# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2022 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_10 _database_code_depnum_ccdc_archive 'CCDC 2125364' loop_ _audit_author_name _audit_author_address 'Sylvain Bernes' ;Instituto de Fisica, BUAP, Puebla Mexico ; _audit_update_record ; 2021-11-30 deposited with the CCDC. 2022-01-21 downloaded from the CCDC. ; # Clave Lab. : ENR-376-1 # Clave IF-UAP: ENR-376-1 # Solicitud: 362 # Firma en la Solicitud: Dr. Joel Luis Teran (ICUAP) # Clave datos : ... \BUAP\Sylvain\ENR-376-1\40mm_1\ _database_code_CAS ? _database_code_CSD ? _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _audit_creation_date 2019-08-30 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point 372 _chemical_formula_moiety 'C16 H20 Br N O4' _chemical_formula_sum 'C16 H20 Br N O4' _chemical_formula_weight 370.24 _chemical_absolute_configuration ad _chemical_optical_rotation ? _chemical_properties_physical ? _chemical_properties_biological ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br 0.1811 1.6452 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _shelx_space_group_comment ? loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.7807(3) _cell_length_b 13.9973(7) _cell_length_c 15.1800(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1653.24(14) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 27617 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 24.52 _exptl_crystal_recrystallization_method ; Re-crystallisation from solvent: CH2Cl2/Petroleum ether ; _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_F_000 760 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.288 _exptl_crystal_size_mid 0.215 _exptl_crystal_size_min 0.150 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 2 -5 5 0.0600 -1 2 -2 0.0450 7 -3 2 0.1450 -1 -5 6 0.1100 0 4 -7 0.1050 -1 -3 5 0.1410 3 5 -1 0.1500 -3 -2 -5 0.1700 3 2 5 0.1760 -3 -5 1 0.1380 _exptl_absorpt_coefficient_mu 1.347 _shelx_estimated_absorpt_T_min 0.698 _shelx_estimated_absorpt_T_max 0.824 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4889 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'X-AREA 1.86 (Stoe & Cie, 2018)' _diffrn_ambient_temperature 295(1) _diffrn_ambient_environment air _diffrn_measurement_specimen_support Mitegen _diffrn_source 'Sealed X-ray tube' _diffrn_source_type 'Axo Astix-f Microfocus source' _diffrn_source_voltage 65 _diffrn_source_current 0.55 _diffrn_source_power 0.03575 _diffrn_radiation_collimation '0.6 mm diameter' _diffrn_radiation_probe x-ray _diffrn_radiation_type AgK\a _diffrn_radiation_wavelength 0.56083 _diffrn_radiation_monochromator 'Graded multilayer mirror' _diffrn_radiation_polarisn_norm -90 _diffrn_measurement_device 'Eulerian four-circle diffractometer' _diffrn_measurement_device_type 'Stoe Stadivari' _diffrn_detector 'Reverse-biased silicon diode array' _diffrn_detector_type 'Dectris Pilatus 100K R' _diffrn_measurement_method '\w scans' _diffrn_measurement_details ; 1149 frames, 50 s/frame, 1 deg./frame, detector distance = 40 mm ; _diffrn_detector_area_resol_mean 5.81 _diffrn_reflns_number 44015 _diffrn_reflns_av_unetI/netI 0.0372 _diffrn_reflns_av_R_equivalents 0.0808 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.321 _diffrn_reflns_theta_max 21.994 _diffrn_reflns_theta_full 19.664 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 4137 _reflns_number_gt 2869 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.750 _reflns_Friedel_fraction_max 0.999 _reflns_Friedel_fraction_full 0.999 _reflns_special_details ? _computing_data_collection 'X-AREA 1.86 (Stoe & Cie, 2018)' _computing_cell_refinement 'X-AREA 1.86' _computing_data_reduction 'X-AREA 1.86' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015a)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)' _computing_publication_material 'PublCif (Westrip, 2010)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0448P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 1005 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.029(8) _refine_ls_number_reflns 4137 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0870 _refine_ls_wR_factor_gt 0.0780 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.05180(6) 0.54800(4) 0.60851(4) 0.06968(19) Uani 1 1 d . . . . . O1 O 0.5818(3) 0.3627(2) 0.79794(19) 0.0460(7) Uani 1 1 d . . . . . C2 C 0.6353(5) 0.3517(3) 0.7088(3) 0.0461(10) Uani 1 1 d . . . . . H2A H 0.634682 0.284846 0.691867 0.055 Uiso 1 1 calc R U . . . H2B H 0.750077 0.377104 0.700375 0.055 Uiso 1 1 calc R U . . . C3 C 0.5037(4) 0.4083(3) 0.6552(3) 0.0379(9) Uani 1 1 d . . . . . H3A H 0.537237 0.475812 0.654275 0.045 Uiso 1 1 calc R U . . . N4 N 0.3510(3) 0.3968(2) 0.7111(2) 0.0369(7) Uani 1 1 d . . . . . C5 C 0.4003(5) 0.3639(3) 0.8013(3) 0.0385(8) Uani 1 1 d . . . . . C6 C 0.4892(4) 0.3724(3) 0.5621(3) 0.0386(9) Uani 1 1 d . . . . . C7 C 0.4269(5) 0.2812(3) 0.5432(3) 0.0460(9) Uani 1 1 d . . . . . H7A H 0.386014 0.243060 0.588762 0.055 Uiso 1 1 calc R U . . . C8 C 0.4251(6) 0.2467(3) 0.4582(3) 0.0567(11) Uani 1 1 d . . . . . H8A H 0.383641 0.185625 0.446787 0.068 Uiso 1 1 calc R U . . . C9 C 0.4847(5) 0.3027(4) 0.3900(3) 0.0621(12) Uani 1 1 d . . . . . H9A H 0.483460 0.279339 0.332689 0.075 Uiso 1 1 calc R U . . . C10 C 0.5459(6) 0.3927(4) 0.4066(3) 0.0579(11) Uani 1 1 d . . . . . H10A H 0.585375 0.430516 0.360503 0.069 Uiso 1 1 calc R U . . . C11 C 0.5491(6) 0.4273(3) 0.4919(3) 0.0465(9) Uani 1 1 d . . . . . H11A H 0.591865 0.488273 0.502611 0.056 Uiso 1 1 calc R U . . . C12 C 0.1892(4) 0.4266(3) 0.6941(3) 0.0400(9) Uani 1 1 d . . . . . O12 O 0.0685(3) 0.4089(2) 0.74342(19) 0.0539(7) Uani 1 1 d . . . . . C13 C 0.1681(4) 0.4835(3) 0.6101(3) 0.0497(10) Uani 1 1 d . . . . . H13A H 0.176349 0.441093 0.559741 0.060 Uiso 1 1 calc R U . . . H13B H 0.259721 0.530297 0.605672 0.060 Uiso 1 1 calc R U . . . C14 C 0.3504(5) 0.4352(3) 0.8729(3) 0.0482(10) Uani 1 1 d . . . . . H14A H 0.400190 0.414820 0.928421 0.058 Uiso 1 1 calc R U . . . H14B H 0.226439 0.434946 0.879587 0.058 Uiso 1 1 calc R U . . . C15 C 0.4100(7) 0.5368(3) 0.8529(4) 0.0679(14) Uani 1 1 d . . . . . H15A H 0.382325 0.577620 0.901622 0.102 Uiso 1 1 calc R U . . . H15B H 0.353043 0.559514 0.800820 0.102 Uiso 1 1 calc R U . . . H15C H 0.531995 0.537017 0.843499 0.102 Uiso 1 1 calc R U . . . C16 C 0.3294(6) 0.2623(3) 0.8147(3) 0.0478(11) Uani 1 1 d . . . . . H16A H 0.205007 0.265702 0.817979 0.057 Uiso 1 1 calc R U . . . H16B H 0.358562 0.224109 0.763518 0.057 Uiso 1 1 calc R U . . . C17 C 0.3951(5) 0.2121(3) 0.8960(3) 0.0452(9) Uani 1 1 d . . . . . O17 O 0.5000(4) 0.1497(2) 0.8953(2) 0.0694(9) Uani 1 1 d . . . . . C18 C 0.3727(7) 0.2012(4) 1.0515(3) 0.0618(13) Uani 1 1 d . . . . . H18A H 0.347127 0.243996 1.099157 0.093 Uiso 1 1 calc R U . . . H18B H 0.494062 0.188893 1.050051 0.093 Uiso 1 1 calc R U . . . H18C H 0.311975 0.142193 1.060059 0.093 Uiso 1 1 calc R U . . . O18 O 0.3195(4) 0.2443(2) 0.9686(2) 0.0552(8) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0541(2) 0.0734(3) 0.0816(4) 0.0243(3) 0.0054(3) 0.0221(2) O1 0.0408(14) 0.0577(18) 0.0395(16) 0.0053(13) -0.0049(13) 0.0005(13) C2 0.0373(18) 0.060(3) 0.041(2) 0.002(2) 0.0014(18) 0.0016(17) C3 0.0364(17) 0.0362(19) 0.041(2) -0.0004(17) 0.0011(16) -0.0047(15) N4 0.0325(13) 0.047(2) 0.0313(18) 0.0032(15) -0.0001(13) 0.0019(13) C5 0.0410(18) 0.042(2) 0.032(2) 0.0030(17) -0.0017(16) -0.0026(15) C6 0.0368(17) 0.042(2) 0.037(2) -0.0003(17) -0.0002(16) 0.0038(14) C7 0.046(2) 0.046(2) 0.046(3) -0.0016(19) 0.002(2) -0.0026(18) C8 0.057(3) 0.053(3) 0.060(3) -0.014(2) -0.005(3) -0.001(2) C9 0.061(2) 0.080(3) 0.045(3) -0.015(3) -0.005(3) 0.010(2) C10 0.064(2) 0.074(3) 0.035(3) 0.006(2) 0.002(2) 0.003(3) C11 0.0528(19) 0.046(2) 0.040(2) 0.0031(17) 0.006(2) -0.001(2) C12 0.0391(17) 0.043(2) 0.038(2) 0.0001(17) -0.0001(17) -0.0004(15) O12 0.0405(13) 0.072(2) 0.0496(18) 0.0095(15) 0.0070(15) 0.0013(14) C13 0.0374(16) 0.062(3) 0.050(3) 0.011(2) 0.004(2) 0.0091(16) C14 0.062(2) 0.046(3) 0.037(3) -0.0010(19) 0.0025(19) -0.0020(18) C15 0.093(4) 0.048(3) 0.063(3) -0.007(2) 0.005(3) -0.007(3) C16 0.059(2) 0.043(2) 0.041(3) 0.0023(19) -0.006(2) -0.003(2) C17 0.0520(19) 0.039(2) 0.045(2) 0.005(2) 0.002(2) -0.0057(16) O17 0.092(2) 0.0528(18) 0.063(2) 0.0092(18) 0.0113(19) 0.0237(17) C18 0.079(3) 0.065(3) 0.042(3) 0.013(2) 0.002(2) -0.004(2) O18 0.0611(18) 0.062(2) 0.0430(19) 0.0110(16) 0.0065(16) 0.0105(15) _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C13 1.935(3) . ? O1 C5 1.413(5) . ? O1 C2 1.424(5) . ? C2 C3 1.530(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N4 1.469(4) . ? C3 C6 1.504(6) . ? C3 H3A 0.9800 . ? N4 C12 1.351(4) . ? N4 C5 1.495(5) . ? C5 C14 1.526(6) . ? C5 C16 1.539(6) . ? C6 C11 1.394(6) . ? C6 C7 1.395(6) . ? C7 C8 1.378(6) . ? C7 H7A 0.9300 . ? C8 C9 1.378(7) . ? C8 H8A 0.9300 . ? C9 C10 1.370(7) . ? C9 H9A 0.9300 . ? C10 C11 1.382(6) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 O12 1.226(4) . ? C12 C13 1.513(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.526(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.509(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O17 1.196(5) . ? C17 O18 1.328(5) . ? C18 O18 1.457(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O1 C2 109.1(3) . . ? O1 C2 C3 104.7(3) . . ? O1 C2 H2A 110.8 . . ? C3 C2 H2A 110.8 . . ? O1 C2 H2B 110.8 . . ? C3 C2 H2B 110.8 . . ? H2A C2 H2B 108.9 . . ? N4 C3 C6 116.5(3) . . ? N4 C3 C2 100.2(3) . . ? C6 C3 C2 112.2(3) . . ? N4 C3 H3A 109.2 . . ? C6 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C12 N4 C3 127.5(3) . . ? C12 N4 C5 120.6(3) . . ? C3 N4 C5 110.9(3) . . ? O1 C5 N4 103.1(3) . . ? O1 C5 C14 106.7(3) . . ? N4 C5 C14 112.7(3) . . ? O1 C5 C16 110.6(3) . . ? N4 C5 C16 108.3(3) . . ? C14 C5 C16 114.8(3) . . ? C11 C6 C7 117.6(4) . . ? C11 C6 C3 120.6(4) . . ? C7 C6 C3 121.7(4) . . ? C8 C7 C6 121.1(4) . . ? C8 C7 H7A 119.4 . . ? C6 C7 H7A 119.4 . . ? C7 C8 C9 120.0(4) . . ? C7 C8 H8A 120.0 . . ? C9 C8 H8A 120.0 . . ? C10 C9 C8 120.1(5) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? C9 C10 C11 120.1(4) . . ? C9 C10 H10A 120.0 . . ? C11 C10 H10A 120.0 . . ? C10 C11 C6 121.1(4) . . ? C10 C11 H11A 119.5 . . ? C6 C11 H11A 119.5 . . ? O12 C12 N4 122.4(4) . . ? O12 C12 C13 122.5(3) . . ? N4 C12 C13 115.1(3) . . ? C12 C13 Br1 110.6(3) . . ? C12 C13 H13A 109.5 . . ? Br1 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? Br1 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C5 C14 C15 112.9(4) . . ? C5 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? C5 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C5 114.6(3) . . ? C17 C16 H16A 108.6 . . ? C5 C16 H16A 108.6 . . ? C17 C16 H16B 108.6 . . ? C5 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? O17 C17 O18 123.8(4) . . ? O17 C17 C16 124.4(5) . . ? O18 C17 C16 111.8(3) . . ? O18 C18 H18A 109.5 . . ? O18 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O18 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 O18 C18 116.8(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O1 C2 C3 36.1(4) . . . . ? O1 C2 C3 N4 -30.7(4) . . . . ? O1 C2 C3 C6 -154.9(3) . . . . ? C6 C3 N4 C12 -53.9(5) . . . . ? C2 C3 N4 C12 -175.1(4) . . . . ? C6 C3 N4 C5 137.7(3) . . . . ? C2 C3 N4 C5 16.5(4) . . . . ? C2 O1 C5 N4 -24.6(4) . . . . ? C2 O1 C5 C14 -143.6(3) . . . . ? C2 O1 C5 C16 91.0(4) . . . . ? C12 N4 C5 O1 -165.7(3) . . . . ? C3 N4 C5 O1 3.6(4) . . . . ? C12 N4 C5 C14 -51.1(5) . . . . ? C3 N4 C5 C14 118.3(3) . . . . ? C12 N4 C5 C16 77.0(4) . . . . ? C3 N4 C5 C16 -113.7(4) . . . . ? N4 C3 C6 C11 135.1(4) . . . . ? C2 C3 C6 C11 -110.3(4) . . . . ? N4 C3 C6 C7 -49.4(5) . . . . ? C2 C3 C6 C7 65.2(4) . . . . ? C11 C6 C7 C8 0.1(6) . . . . ? C3 C6 C7 C8 -175.5(4) . . . . ? C6 C7 C8 C9 -0.3(7) . . . . ? C7 C8 C9 C10 0.0(7) . . . . ? C8 C9 C10 C11 0.4(7) . . . . ? C9 C10 C11 C6 -0.6(7) . . . . ? C7 C6 C11 C10 0.4(6) . . . . ? C3 C6 C11 C10 176.0(4) . . . . ? C3 N4 C12 O12 176.1(4) . . . . ? C5 N4 C12 O12 -16.5(6) . . . . ? C3 N4 C12 C13 -4.1(6) . . . . ? C5 N4 C12 C13 163.3(3) . . . . ? O12 C12 C13 Br1 14.1(5) . . . . ? N4 C12 C13 Br1 -165.6(3) . . . . ? O1 C5 C14 C15 62.2(5) . . . . ? N4 C5 C14 C15 -50.3(5) . . . . ? C16 C5 C14 C15 -174.9(4) . . . . ? O1 C5 C16 C17 57.2(5) . . . . ? N4 C5 C16 C17 169.5(3) . . . . ? C14 C5 C16 C17 -63.7(5) . . . . ? C5 C16 C17 O17 -105.0(5) . . . . ? C5 C16 C17 O18 76.3(4) . . . . ? O17 C17 O18 C18 1.3(6) . . . . ? C16 C17 O18 C18 -180.0(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C2 H2B O12 0.97 2.60 3.504(5) 155.1 1_655 yes C3 H3A O17 0.98 2.56 3.465(5) 152.7 3_656 yes C13 H13B O17 0.97 2.51 3.476(5) 176.3 3_656 yes C14 H14A Br1 0.97 3.02 3.912(4) 153.0 2_565 yes C14 H14A O18 0.97 2.54 3.050(5) 112.7 . yes C14 H14B O12 0.97 2.43 2.968(5) 114.5 . yes C16 H16A O12 0.97 2.54 3.083(5) 115.7 . yes _refine_diff_density_max 0.500 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.049 _shelx_res_file ; TITL enr-376-1_a.res in P2(1)2(1)2(1) ENR-376-1.res created by SHELXL-2018/3 at 17:35:41 on 30-Aug-2019 CELL 0.56083 7.7807 13.9973 15.1800 90 90 90 ZERR 4 0.0003 0.0007 0.0008 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O Br UNIT 64 80 4 16 4 TEMP 22 SIZE 0.288 0.215 0.150 L.S. 12 PLAN 20 BOND $H CONF EQIV $1 x+1, y, z EQIV $2 -x+1, y+1/2, -z+3/2 EQIV $3 -x+1/2, -y+1, z+1/2 HTAB C2 O12_$1 HTAB C3 O17_$2 HTAB C13 O17_$2 HTAB C14 Br1_$3 HTAB C14 O18 HTAB C14 O12 HTAB C16 O12 LIST 4 FMAP 2 ACTA WGHT 0.044800 FVAR 0.49604 BR1 5 -0.051797 0.547995 0.608508 11.00000 0.05409 0.07337 = 0.08157 0.02430 0.00538 0.02214 O1 4 0.581764 0.362683 0.797942 11.00000 0.04076 0.05772 = 0.03953 0.00533 -0.00491 0.00049 C2 1 0.635297 0.351659 0.708828 11.00000 0.03733 0.05955 = 0.04128 0.00235 0.00143 0.00160 AFIX 23 H2A 2 0.634682 0.284846 0.691867 11.00000 -1.20000 H2B 2 0.750077 0.377104 0.700375 11.00000 -1.20000 AFIX 0 C3 1 0.503730 0.408328 0.655162 11.00000 0.03644 0.03622 = 0.04091 -0.00041 0.00106 -0.00465 AFIX 13 H3A 2 0.537237 0.475812 0.654275 11.00000 -1.20000 AFIX 0 N4 3 0.351039 0.396785 0.711107 11.00000 0.03253 0.04685 = 0.03126 0.00324 -0.00014 0.00190 C5 1 0.400312 0.363867 0.801301 11.00000 0.04105 0.04235 = 0.03196 0.00302 -0.00167 -0.00258 C6 1 0.489173 0.372449 0.562088 11.00000 0.03681 0.04172 = 0.03723 -0.00029 -0.00018 0.00381 C7 1 0.426943 0.281215 0.543204 11.00000 0.04592 0.04607 = 0.04614 -0.00164 0.00214 -0.00256 AFIX 43 H7A 2 0.386014 0.243060 0.588762 11.00000 -1.20000 AFIX 0 C8 1 0.425116 0.246701 0.458181 11.00000 0.05691 0.05326 = 0.05981 -0.01353 -0.00472 -0.00061 AFIX 43 H8A 2 0.383641 0.185625 0.446787 11.00000 -1.20000 AFIX 0 C9 1 0.484750 0.302692 0.390041 11.00000 0.06111 0.08002 = 0.04525 -0.01535 -0.00535 0.01006 AFIX 43 H9A 2 0.483460 0.279339 0.332689 11.00000 -1.20000 AFIX 0 C10 1 0.545929 0.392695 0.406638 11.00000 0.06439 0.07437 = 0.03491 0.00600 0.00202 0.00264 AFIX 43 H10A 2 0.585375 0.430516 0.360503 11.00000 -1.20000 AFIX 0 C11 1 0.549070 0.427333 0.491902 11.00000 0.05279 0.04643 = 0.04042 0.00314 0.00632 -0.00110 AFIX 43 H11A 2 0.591865 0.488273 0.502611 11.00000 -1.20000 AFIX 0 C12 1 0.189197 0.426564 0.694103 11.00000 0.03906 0.04258 = 0.03832 0.00011 -0.00006 -0.00036 O12 4 0.068485 0.408941 0.743415 11.00000 0.04049 0.07153 = 0.04960 0.00947 0.00697 0.00135 C13 1 0.168127 0.483530 0.610082 11.00000 0.03742 0.06199 = 0.04955 0.01148 0.00444 0.00911 AFIX 23 H13A 2 0.176349 0.441093 0.559741 11.00000 -1.20000 H13B 2 0.259721 0.530297 0.605672 11.00000 -1.20000 AFIX 0 C14 1 0.350424 0.435151 0.872913 11.00000 0.06212 0.04591 = 0.03662 -0.00095 0.00246 -0.00200 AFIX 23 H14A 2 0.400190 0.414820 0.928421 11.00000 -1.20000 H14B 2 0.226439 0.434946 0.879587 11.00000 -1.20000 AFIX 0 C15 1 0.409971 0.536750 0.852853 11.00000 0.09271 0.04785 = 0.06323 -0.00735 0.00468 -0.00667 AFIX 137 H15A 2 0.382325 0.577620 0.901622 11.00000 -1.50000 H15B 2 0.353043 0.559514 0.800820 11.00000 -1.50000 H15C 2 0.531995 0.537017 0.843499 11.00000 -1.50000 AFIX 0 C16 1 0.329359 0.262288 0.814703 11.00000 0.05927 0.04278 = 0.04141 0.00226 -0.00596 -0.00340 AFIX 23 H16A 2 0.205007 0.265702 0.817979 11.00000 -1.20000 H16B 2 0.358562 0.224109 0.763518 11.00000 -1.20000 AFIX 0 C17 1 0.395089 0.212117 0.895971 11.00000 0.05201 0.03892 = 0.04481 0.00543 0.00193 -0.00567 O17 4 0.500006 0.149708 0.895348 11.00000 0.09244 0.05281 = 0.06294 0.00920 0.01128 0.02373 C18 1 0.372708 0.201173 1.051531 11.00000 0.07865 0.06522 = 0.04158 0.01297 0.00217 -0.00351 AFIX 137 H18A 2 0.347127 0.243996 1.099157 11.00000 -1.50000 H18B 2 0.494062 0.188893 1.050051 11.00000 -1.50000 H18C 2 0.311975 0.142193 1.060059 11.00000 -1.50000 AFIX 0 O18 4 0.319542 0.244318 0.968572 11.00000 0.06113 0.06156 = 0.04300 0.01096 0.00653 0.01047 HKLF 4 REM enr-376-1_a.res in P2(1)2(1)2(1) REM wR2 = 0.0870, GooF = S = 0.987, Restrained GooF = 0.987 for all data REM R1 = 0.0356 for 2869 Fo > 4sig(Fo) and 0.0646 for all 4137 data REM 201 parameters refined using 0 restraints END WGHT 0.0446 0.0000 REM Highest difference peak 0.500, deepest hole -0.359, 1-sigma level 0.049 Q1 1 0.0322 0.5809 0.6336 11.00000 0.05 0.50 Q2 1 -0.0856 0.5572 0.5932 11.00000 0.05 0.26 Q3 1 -0.0375 0.5145 0.5963 11.00000 0.05 0.23 Q4 1 0.0782 0.4895 0.5992 11.00000 0.05 0.21 Q5 1 -0.1150 0.5517 0.6407 11.00000 0.05 0.19 Q6 1 -0.1013 0.4563 0.6021 11.00000 0.05 0.17 Q7 1 0.0192 0.4828 0.6541 11.00000 0.05 0.17 Q8 1 0.5437 0.1823 0.8801 11.00000 0.05 0.17 Q9 1 0.1928 0.1827 0.9227 11.00000 0.05 0.16 Q10 1 0.1619 0.1907 0.9364 11.00000 0.05 0.15 Q11 1 0.5536 0.4469 0.6584 11.00000 0.05 0.15 Q12 1 0.7522 0.3622 0.7414 11.00000 0.05 0.15 Q13 1 0.6736 0.5192 0.4377 11.00000 0.05 0.15 Q14 1 0.5543 0.2016 0.5961 11.00000 0.05 0.15 Q15 1 0.4786 0.1855 0.9184 11.00000 0.05 0.15 Q16 1 -0.0029 0.4571 0.7393 11.00000 0.05 0.15 Q17 1 0.7221 0.5719 0.6904 11.00000 0.05 0.15 Q18 1 -0.2109 0.5766 0.6167 11.00000 0.05 0.15 Q19 1 -0.0055 0.4658 0.6203 11.00000 0.05 0.14 Q20 1 0.1060 0.4144 0.5662 11.00000 0.05 0.14 ; _shelx_res_checksum 74684 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_24a _database_code_depnum_ccdc_archive 'CCDC 2125367' loop_ _audit_author_name _audit_author_address 'Sylvain Bernes' ;Instituto de Fisica, BUAP, Puebla Mexico ; _audit_update_record ; 2021-11-30 deposited with the CCDC. 2022-01-21 downloaded from the CCDC. ; # start Validation Reply Form _vrf_RINTA01_24a ; PROBLEM: The value of Rint is greater than 0.25 RESPONSE: The crystal crystallizes in a ncs space group, with Z' = 3 and Z = 12, and is the an intrinsically poorly diffracting sample. Moreover, thickness of the single crystals is limited to 0.07 micras. ; _vrf_PLAT026_24a ; PROBLEM: Ratio Observed / Unique Reflections (too) Low .. 33% Check RESPONSE: The crystal crystallizes in a ncs space group, with Z' = 3 and Z = 12, and is the an intrinsically poorly diffracting sample. Moreover, thickness of the single crystals is limited to 0.07 micras. ; # Added during the CSD deposition process: Tuesday 30 November 2021 08:37 PM # end Validation Reply Form # Clave Lab. : ENR-410-1 # Clave IF-UAP: ENR-410-1 # Solicitud: 393 # Firma en la Solicitud: Dr. David Aparicio (ICUAP) # Clave datos : ... \BUAP\Sylvain\ENR-410-1\70mm_1\ _database_code_CAS ? _database_code_CSD ? _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _audit_creation_date 2019-10-20 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point 423 _chemical_formula_moiety 'C17 H21 N O3 S' _chemical_formula_sum 'C17 H21 N O3 S' _chemical_formula_weight 319.41 _chemical_absolute_configuration ad _chemical_optical_rotation ? _chemical_properties_physical ? _chemical_properties_biological ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.0826 0.0763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _shelx_space_group_comment ? loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.4670(2) _cell_length_b 27.8275(12) _cell_length_c 32.842(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4996.4(4) _cell_formula_units_Z 12 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 12011 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 19.60 _exptl_crystal_recrystallization_method ; Re-crystallisation from solvent: AcOEt/benzine ; _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_F_000 2040 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.458 _exptl_crystal_size_mid 0.092 _exptl_crystal_size_min 0.069 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 5 0.0290 2 -1 -9 0.0400 0 0 -1 0.0440 0 0 1 0.0480 1 4 0 0.2520 -2 -9 0 0.2060 _exptl_absorpt_coefficient_mu 0.114 _shelx_estimated_absorpt_T_min 0.950 _shelx_estimated_absorpt_T_max 0.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2503 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'X-AREA 1.86 (Stoe & Cie, 2018)' _diffrn_ambient_temperature 295(1) _diffrn_ambient_environment air _diffrn_measurement_specimen_support Mitegen _diffrn_source 'Sealed X-ray tube' _diffrn_source_type 'Axo Astix-f Microfocus source' _diffrn_source_voltage 65 _diffrn_source_current 0.55 _diffrn_source_power 0.03575 _diffrn_radiation_collimation '0.6 mm diameter' _diffrn_radiation_probe x-ray _diffrn_radiation_type AgK\a _diffrn_radiation_wavelength 0.56083 _diffrn_radiation_monochromator 'Graded multilayer mirror' _diffrn_radiation_polarisn_norm -90 _diffrn_measurement_device 'Eulerian four-circle diffractometer' _diffrn_measurement_device_type 'Stoe Stadivari' _diffrn_detector 'Reverse-biased silicon diode array' _diffrn_detector_type 'Dectris Pilatus 100K R' _diffrn_measurement_method '\w scans' _diffrn_measurement_details ; 1742 frames, 70-100 s/frame, 1 deg./frame, detector distance = 70 mm ; _diffrn_detector_area_resol_mean 5.81 _diffrn_reflns_number 87513 _diffrn_reflns_av_unetI/netI 0.2287 _diffrn_reflns_av_R_equivalents 0.2841 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.271 _diffrn_reflns_theta_max 19.999 _diffrn_reflns_theta_full 19.664 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 9490 _reflns_number_gt 3129 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.743 _reflns_Friedel_fraction_max 1.000 _reflns_Friedel_fraction_full 1.000 _reflns_special_details ? _computing_data_collection 'X-AREA 1.86 (Stoe & Cie, 2018)' _computing_cell_refinement 'X-AREA 1.86' _computing_data_reduction 'X-AREA 1.86' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015a)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)' _computing_publication_material 'PublCif (Westrip, 2010)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0114P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_extinction_coef 0.00060(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Flack x determined using 941 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.01(15) _refine_ls_number_reflns 9490 _refine_ls_number_parameters 605 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1652 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0699 _refine_ls_goodness_of_fit_ref 0.647 _refine_ls_restrained_S_all 0.647 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.8586(3) 0.52611(7) 0.89092(6) 0.0666(6) Uani 1 1 d . . . . . N1 N 0.8117(9) 0.63546(19) 0.96566(16) 0.0489(14) Uani 1 1 d . . . . . C2 C 0.8645(12) 0.5906(3) 0.9493(2) 0.0536(18) Uani 1 1 d . . . . . O2 O 0.9953(7) 0.56257(17) 0.97014(15) 0.0688(14) Uani 1 1 d . . . . . C3 C 0.7564(11) 0.5793(2) 0.9116(2) 0.0513(18) Uani 1 1 d . . . . . C4 C 0.5628(12) 0.6054(3) 0.8940(2) 0.059(2) Uani 1 1 d . . . . . O4 O 0.4506(9) 0.59342(19) 0.86184(16) 0.0853(16) Uani 1 1 d . . . . . C5 C 0.4710(11) 0.6481(3) 0.9181(2) 0.064(2) Uani 1 1 d . . . . . H5A H 0.343508 0.637515 0.936566 0.076 Uiso 1 1 calc R U . . . H5B H 0.399879 0.671310 0.899516 0.076 Uiso 1 1 calc R U . . . C6 C 0.6775(12) 0.6724(3) 0.9427(2) 0.0551(18) Uani 1 1 d . . . . . O6 O 0.5686(9) 0.70005(16) 0.97431(16) 0.0724(14) Uani 1 1 d . . . . . C7 C 0.7449(13) 0.7000(3) 1.0066(2) 0.077(2) Uani 1 1 d . . . . . H7A H 0.668340 0.708356 1.032316 0.092 Uiso 1 1 calc R U . . . H7B H 0.875000 0.722788 1.001101 0.092 Uiso 1 1 calc R U . . . C8 C 0.8451(12) 0.6484(2) 1.0079(2) 0.0527(18) Uani 1 1 d . . . . . H8A H 1.019210 0.648476 1.015019 0.063 Uiso 1 1 calc R U . . . C9 C 0.8454(12) 0.7027(2) 0.9166(2) 0.069(2) Uani 1 1 d . . . . . H9A H 0.986228 0.711878 0.932744 0.082 Uiso 1 1 calc R U . . . H9B H 0.904088 0.683028 0.894213 0.082 Uiso 1 1 calc R U . . . C10 C 0.7325(14) 0.7472(3) 0.8993(3) 0.136(4) Uani 1 1 d . . . . . H10A H 0.851982 0.764205 0.883450 0.205 Uiso 1 1 calc R U . . . H10B H 0.676454 0.767363 0.921100 0.205 Uiso 1 1 calc R U . . . H10C H 0.596697 0.738585 0.882272 0.205 Uiso 1 1 calc R U . . . C11 C 0.9181(13) 0.5373(3) 0.8386(2) 0.086(2) Uani 1 1 d . . . . . H11A H 0.959929 0.507744 0.825245 0.128 Uiso 1 1 calc R U . . . H11B H 1.051625 0.559558 0.836112 0.128 Uiso 1 1 calc R U . . . H11C H 0.774917 0.550775 0.826039 0.128 Uiso 1 1 calc R U . . . C12 C 0.5872(10) 0.4888(2) 0.8872(2) 0.075(2) Uani 1 1 d . . . . . H12A H 0.622898 0.460935 0.871088 0.112 Uiso 1 1 calc R U . . . H12B H 0.457906 0.506826 0.874585 0.112 Uiso 1 1 calc R U . . . H12C H 0.537188 0.479068 0.913969 0.112 Uiso 1 1 calc R U . . . C13 C 0.7011(12) 0.6185(2) 1.0378(2) 0.0514(18) Uani 1 1 d . . . . . C14 C 0.7686(13) 0.6174(3) 1.0780(2) 0.069(2) Uani 1 1 d . . . . . H14A H 0.910555 0.633227 1.086007 0.083 Uiso 1 1 calc R U . . . C15 C 0.6324(16) 0.5937(3) 1.1065(2) 0.083(2) Uani 1 1 d . . . . . H15A H 0.679982 0.593839 1.133716 0.099 Uiso 1 1 calc R U . . . C16 C 0.4219(15) 0.5693(3) 1.0946(3) 0.078(2) Uani 1 1 d . . . . . H16A H 0.329153 0.552792 1.113784 0.094 Uiso 1 1 calc R U . . . C17 C 0.3507(12) 0.5695(2) 1.0542(3) 0.068(2) Uani 1 1 d . . . . . H17A H 0.209499 0.553443 1.046165 0.082 Uiso 1 1 calc R U . . . C18 C 0.4918(12) 0.5938(2) 1.0258(2) 0.0577(19) Uani 1 1 d . . . . . H18A H 0.446270 0.593558 0.998533 0.069 Uiso 1 1 calc R U . . . S21 S 0.6737(3) 0.51084(7) 0.72689(6) 0.0606(5) Uani 1 1 d . . . . . N21 N 0.6676(9) 0.37959(19) 0.77136(17) 0.0495(14) Uani 1 1 d . . . . . C22 C 0.6261(11) 0.4282(2) 0.7684(2) 0.0475(17) Uani 1 1 d . . . . . O22 O 0.4822(7) 0.44838(15) 0.79200(13) 0.0582(12) Uani 1 1 d . . . . . C23 C 0.7674(10) 0.4527(2) 0.7371(2) 0.0512(18) Uani 1 1 d . . . . . C24 C 0.9719(12) 0.4324(3) 0.7174(2) 0.057(2) Uani 1 1 d . . . . . O24 O 1.1060(8) 0.45398(17) 0.69195(14) 0.0698(14) Uani 1 1 d . . . . . C25 C 1.0411(11) 0.3819(2) 0.7306(2) 0.064(2) Uani 1 1 d . . . . . H25A H 1.151175 0.383689 0.753713 0.077 Uiso 1 1 calc R U . . . H25B H 1.127023 0.365974 0.708544 0.077 Uiso 1 1 calc R U . . . C26 C 0.8167(11) 0.3522(2) 0.7423(2) 0.0522(18) Uani 1 1 d . . . . . O26 O 0.8911(7) 0.31181(15) 0.76637(14) 0.0613(13) Uani 1 1 d . . . . . C27 C 0.6874(11) 0.3008(2) 0.7924(2) 0.060(2) Uani 1 1 d . . . . . H27A H 0.736678 0.280609 0.815015 0.072 Uiso 1 1 calc R U . . . H27B H 0.557202 0.285062 0.777446 0.072 Uiso 1 1 calc R U . . . C28 C 0.6071(11) 0.3516(2) 0.80735(19) 0.0490(17) Uani 1 1 d . . . . . H28A H 0.430027 0.352140 0.811989 0.059 Uiso 1 1 calc R U . . . C29 C 0.6611(12) 0.3355(3) 0.70623(19) 0.068(2) Uani 1 1 d . . . . . H29A H 0.514193 0.320189 0.716550 0.081 Uiso 1 1 calc R U . . . H29B H 0.611499 0.363306 0.690498 0.081 Uiso 1 1 calc R U . . . C30 C 0.7932(14) 0.3005(3) 0.6783(2) 0.103(3) Uani 1 1 d . . . . . H30A H 0.683337 0.289717 0.657446 0.155 Uiso 1 1 calc R U . . . H30B H 0.848907 0.273389 0.693880 0.155 Uiso 1 1 calc R U . . . H30C H 0.930964 0.316240 0.666067 0.155 Uiso 1 1 calc R U . . . C31 C 0.6143(12) 0.5135(3) 0.67307(18) 0.073(2) Uani 1 1 d . . . . . H31A H 0.589445 0.546322 0.665085 0.110 Uiso 1 1 calc R U . . . H31B H 0.470443 0.495111 0.666906 0.110 Uiso 1 1 calc R U . . . H31C H 0.751393 0.500484 0.658506 0.110 Uiso 1 1 calc R U . . . C32 C 0.9452(10) 0.5468(2) 0.7299(2) 0.074(2) Uani 1 1 d . . . . . H32A H 0.927132 0.574659 0.712937 0.111 Uiso 1 1 calc R U . . . H32B H 1.083054 0.528320 0.720890 0.111 Uiso 1 1 calc R U . . . H32C H 0.970604 0.556739 0.757609 0.111 Uiso 1 1 calc R U . . . C33 C 0.7397(11) 0.3658(2) 0.8456(2) 0.0480(17) Uani 1 1 d . . . . . C34 C 0.6595(12) 0.3496(2) 0.8831(2) 0.0604(19) Uani 1 1 d . . . . . H34A H 0.518112 0.331124 0.884345 0.072 Uiso 1 1 calc R U . . . C35 C 0.7824(13) 0.3601(3) 0.9186(2) 0.066(2) Uani 1 1 d . . . . . H35A H 0.723731 0.348993 0.943451 0.079 Uiso 1 1 calc R U . . . C36 C 0.9940(13) 0.3873(3) 0.9170(3) 0.072(2) Uani 1 1 d . . . . . H36A H 1.077198 0.395023 0.940801 0.086 Uiso 1 1 calc R U . . . C37 C 1.0805(13) 0.4029(3) 0.8800(3) 0.073(2) Uani 1 1 d . . . . . H37A H 1.224287 0.420750 0.878970 0.088 Uiso 1 1 calc R U . . . C38 C 0.9580(11) 0.3927(2) 0.8446(2) 0.0538(18) Uani 1 1 d . . . . . H38A H 1.019209 0.403489 0.819839 0.065 Uiso 1 1 calc R U . . . S41 S 1.0891(3) 0.05503(7) 0.93908(6) 0.0615(5) Uani 1 1 d . . . . . N41 N 1.1370(9) 0.1758(2) 0.87795(17) 0.0517(14) Uani 1 1 d . . . . . C42 C 1.0811(11) 0.1288(3) 0.8865(2) 0.0497(17) Uani 1 1 d . . . . . O42 O 0.9400(7) 0.10576(16) 0.86381(13) 0.0614(13) Uani 1 1 d . . . . . C43 C 1.1979(11) 0.1103(2) 0.9227(2) 0.0547(19) Uani 1 1 d . . . . . C44 C 1.3972(12) 0.1334(3) 0.9432(2) 0.0595(19) Uani 1 1 d . . . . . O44 O 1.4988(8) 0.11687(17) 0.97447(15) 0.0701(15) Uani 1 1 d . . . . . C45 C 1.4883(10) 0.1788(2) 0.9236(2) 0.058(2) Uani 1 1 d . . . . . H45A H 1.605308 0.170835 0.902457 0.070 Uiso 1 1 calc R U . . . H45B H 1.571364 0.198324 0.943803 0.070 Uiso 1 1 calc R U . . . C46 C 1.2804(11) 0.2073(3) 0.9053(2) 0.0519(18) Uani 1 1 d . . . . . O46 O 1.3711(7) 0.24233(16) 0.87747(13) 0.0580(12) Uani 1 1 d . . . . . C47 C 1.1760(12) 0.2498(2) 0.8490(2) 0.065(2) Uani 1 1 d . . . . . H47A H 1.235446 0.265795 0.824711 0.078 Uiso 1 1 calc R U . . . H47B H 1.047627 0.269256 0.861067 0.078 Uiso 1 1 calc R U . . . C48 C 1.0825(11) 0.2000(2) 0.8391(2) 0.0528(18) Uani 1 1 d . . . . . H48A H 0.905572 0.200732 0.834330 0.063 Uiso 1 1 calc R U . . . C49 C 1.1165(11) 0.2311(2) 0.9372(2) 0.0587(19) Uani 1 1 d . . . . . H49A H 0.974832 0.244910 0.923835 0.070 Uiso 1 1 calc R U . . . H49B H 1.058990 0.206889 0.956170 0.070 Uiso 1 1 calc R U . . . C50 C 1.2495(12) 0.2704(3) 0.9608(2) 0.076(2) Uani 1 1 d . . . . . H50A H 1.131853 0.291253 0.973488 0.114 Uiso 1 1 calc R U . . . H50B H 1.349552 0.288753 0.942492 0.114 Uiso 1 1 calc R U . . . H50C H 1.350780 0.256081 0.981377 0.114 Uiso 1 1 calc R U . . . C51 C 1.0124(12) 0.0607(3) 0.9918(2) 0.083(2) Uani 1 1 d . . . . . H51A H 0.953783 0.030365 1.001776 0.124 Uiso 1 1 calc R U . . . H51B H 0.887186 0.084561 0.994931 0.124 Uiso 1 1 calc R U . . . H51C H 1.154886 0.070075 1.006850 0.124 Uiso 1 1 calc R U . . . C52 C 1.3549(10) 0.0172(2) 0.9426(2) 0.072(2) Uani 1 1 d . . . . . H52A H 1.308039 -0.013840 0.952605 0.108 Uiso 1 1 calc R U . . . H52B H 1.471113 0.031465 0.960854 0.108 Uiso 1 1 calc R U . . . H52C H 1.427420 0.013859 0.916099 0.108 Uiso 1 1 calc R U . . . C53 C 1.2112(12) 0.1791(2) 0.8029(2) 0.0505(18) Uani 1 1 d . . . . . C54 C 1.1237(14) 0.1892(3) 0.7645(2) 0.073(2) Uani 1 1 d . . . . . H54A H 0.980629 0.207043 0.761859 0.088 Uiso 1 1 calc R U . . . C55 C 1.2432(18) 0.1736(3) 0.7293(3) 0.102(3) Uani 1 1 d . . . . . H55A H 1.182331 0.180870 0.703595 0.123 Uiso 1 1 calc R U . . . C56 C 1.4578(18) 0.1465(3) 0.7340(3) 0.095(3) Uani 1 1 d . . . . . H56A H 1.540051 0.135220 0.711116 0.114 Uiso 1 1 calc R U . . . C57 C 1.5446(15) 0.1369(3) 0.7711(3) 0.088(3) Uani 1 1 d . . . . . H57A H 1.689077 0.119490 0.773450 0.105 Uiso 1 1 calc R U . . . C58 C 1.4258(12) 0.1522(3) 0.8067(2) 0.064(2) Uani 1 1 d . . . . . H58A H 1.488342 0.144501 0.832197 0.077 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0613(10) 0.0659(13) 0.0724(14) -0.0156(11) -0.0020(11) 0.0048(10) N1 0.049(3) 0.041(4) 0.056(4) -0.003(3) -0.006(3) 0.000(3) C2 0.048(4) 0.048(5) 0.064(5) -0.003(4) 0.001(4) 0.003(4) O2 0.070(3) 0.058(3) 0.079(4) -0.005(3) -0.014(3) 0.010(3) C3 0.049(4) 0.048(4) 0.057(5) -0.015(4) -0.004(4) 0.007(4) C4 0.057(4) 0.054(5) 0.065(5) 0.004(5) -0.001(4) 0.002(4) O4 0.078(3) 0.103(4) 0.074(4) -0.007(3) -0.022(3) 0.006(3) C5 0.051(4) 0.064(5) 0.076(5) 0.018(4) -0.008(4) 0.005(4) C6 0.050(4) 0.055(5) 0.061(5) 0.006(4) 0.004(4) 0.013(4) O6 0.082(3) 0.050(3) 0.086(4) 0.000(3) 0.013(3) 0.013(3) C7 0.081(5) 0.057(6) 0.092(7) -0.007(5) 0.005(5) -0.012(5) C8 0.052(4) 0.038(4) 0.068(5) -0.010(4) -0.004(4) 0.001(4) C9 0.068(4) 0.051(5) 0.087(6) 0.012(4) 0.016(5) 0.009(4) C10 0.118(7) 0.103(8) 0.189(11) 0.097(8) 0.042(7) 0.031(6) C11 0.095(5) 0.088(6) 0.074(6) -0.015(5) 0.021(5) -0.011(5) C12 0.055(4) 0.061(5) 0.108(6) -0.014(5) 0.003(4) -0.011(4) C13 0.050(4) 0.039(4) 0.064(5) -0.004(4) 0.001(4) 0.002(4) C14 0.068(5) 0.077(6) 0.063(6) -0.007(5) 0.000(5) -0.013(4) C15 0.094(6) 0.096(7) 0.059(5) -0.015(5) -0.009(5) -0.004(6) C16 0.091(6) 0.067(6) 0.076(6) 0.016(5) 0.017(5) 0.006(5) C17 0.058(4) 0.061(5) 0.085(6) 0.009(5) 0.004(5) -0.008(4) C18 0.057(4) 0.057(5) 0.059(5) 0.015(4) 0.001(4) 0.007(4) S21 0.0614(11) 0.0524(12) 0.0680(13) 0.0088(11) 0.0050(11) -0.0054(11) N21 0.048(3) 0.044(4) 0.056(4) 0.003(3) 0.014(3) 0.007(3) C22 0.043(4) 0.041(5) 0.058(5) 0.000(4) -0.007(4) -0.003(4) O22 0.059(3) 0.047(3) 0.069(3) 0.000(3) 0.014(2) 0.004(3) C23 0.048(4) 0.036(4) 0.069(5) 0.010(4) 0.003(4) 0.009(4) C24 0.055(4) 0.055(5) 0.061(5) -0.008(4) -0.002(4) 0.004(4) O24 0.070(3) 0.076(4) 0.063(3) 0.002(3) 0.020(3) -0.009(3) C25 0.051(4) 0.069(5) 0.071(5) -0.004(4) 0.006(4) 0.007(4) C26 0.050(4) 0.045(4) 0.061(5) -0.007(4) -0.004(4) 0.000(4) O26 0.062(3) 0.047(3) 0.075(3) 0.004(3) -0.002(3) 0.012(3) C27 0.055(4) 0.052(5) 0.072(5) 0.010(4) 0.003(4) -0.010(4) C28 0.045(4) 0.042(4) 0.060(5) -0.003(4) -0.002(4) 0.006(4) C29 0.069(4) 0.072(5) 0.062(5) -0.016(4) 0.001(4) 0.000(5) C30 0.111(6) 0.098(7) 0.101(7) -0.040(6) 0.004(6) 0.022(6) C31 0.088(5) 0.067(5) 0.065(5) 0.012(4) -0.016(5) -0.017(5) C32 0.075(5) 0.063(5) 0.085(5) -0.007(5) -0.004(4) -0.027(4) C33 0.051(4) 0.030(4) 0.063(5) -0.004(4) -0.002(4) 0.006(3) C34 0.065(4) 0.044(4) 0.073(5) 0.003(4) -0.008(5) -0.001(4) C35 0.083(5) 0.052(5) 0.064(6) 0.002(4) -0.006(5) -0.002(5) C36 0.073(5) 0.062(6) 0.081(6) -0.014(5) -0.021(5) 0.004(5) C37 0.057(4) 0.073(6) 0.090(6) -0.001(5) -0.014(5) -0.014(4) C38 0.045(4) 0.048(4) 0.068(5) 0.001(4) 0.000(4) -0.003(4) S41 0.0566(10) 0.0522(12) 0.0758(14) 0.0096(11) -0.0060(10) -0.0028(10) N41 0.050(3) 0.047(4) 0.058(4) 0.003(3) -0.010(3) -0.004(3) C42 0.047(4) 0.043(5) 0.059(5) 0.009(4) -0.003(4) 0.005(4) O42 0.063(3) 0.053(3) 0.068(3) -0.002(3) -0.016(3) -0.004(3) C43 0.057(4) 0.040(4) 0.067(5) 0.012(4) 0.001(4) -0.015(4) C44 0.053(4) 0.047(5) 0.079(6) -0.004(4) -0.004(4) -0.005(4) O44 0.063(3) 0.070(4) 0.078(4) 0.010(3) -0.027(3) 0.000(3) C45 0.044(4) 0.058(5) 0.073(5) -0.001(4) -0.004(4) 0.002(4) C46 0.048(4) 0.051(5) 0.057(5) -0.003(4) -0.001(4) -0.003(4) O46 0.057(3) 0.055(3) 0.062(3) 0.006(3) 0.001(3) -0.009(3) C47 0.071(5) 0.047(5) 0.078(5) 0.005(4) -0.006(5) 0.000(4) C48 0.048(4) 0.043(4) 0.068(5) 0.010(4) -0.003(4) 0.006(4) C49 0.059(4) 0.050(5) 0.066(5) 0.004(4) 0.000(4) -0.001(4) C50 0.087(5) 0.063(5) 0.079(6) -0.016(5) -0.004(4) 0.003(4) C51 0.084(5) 0.081(6) 0.083(6) 0.018(5) 0.026(4) 0.008(5) C52 0.062(4) 0.057(5) 0.097(6) 0.007(5) -0.007(5) 0.024(4) C53 0.055(4) 0.042(4) 0.055(5) -0.003(4) 0.004(4) -0.011(4) C54 0.086(5) 0.072(6) 0.062(5) -0.002(5) -0.003(5) -0.003(5) C55 0.136(8) 0.089(7) 0.082(7) -0.005(6) 0.011(7) 0.006(6) C56 0.105(7) 0.089(7) 0.091(8) -0.005(7) 0.032(7) -0.004(6) C57 0.080(6) 0.063(6) 0.119(8) -0.001(6) 0.014(7) 0.007(5) C58 0.054(4) 0.060(5) 0.078(6) -0.014(5) 0.009(4) 0.001(4) _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C3 1.721(7) . ? S1 C11 1.778(7) . ? S1 C12 1.814(6) . ? N1 C2 1.388(8) . ? N1 C8 1.445(7) . ? N1 C6 1.471(8) . ? C2 O2 1.260(7) . ? C2 C3 1.409(8) . ? C3 C4 1.407(8) . ? C4 O4 1.267(7) . ? C4 C5 1.511(9) . ? C5 C6 1.546(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O6 1.421(7) . ? C6 C9 1.513(8) . ? O6 C7 1.433(7) . ? C7 C8 1.537(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C13 1.509(9) . ? C8 H8A 0.9800 . ? C9 C10 1.495(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.370(9) . ? C13 C18 1.393(8) . ? C14 C15 1.368(9) . ? C14 H14A 0.9300 . ? C15 C16 1.393(10) . ? C15 H15A 0.9300 . ? C16 C17 1.381(9) . ? C16 H16A 0.9300 . ? C17 C18 1.387(8) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? S21 C23 1.729(6) . ? S21 C32 1.793(6) . ? S21 C31 1.799(6) . ? N21 C22 1.375(7) . ? N21 C28 1.454(7) . ? N21 C26 1.469(7) . ? C22 O22 1.240(7) . ? C22 C23 1.454(8) . ? C23 C24 1.411(8) . ? C24 O24 1.263(7) . ? C24 C25 1.519(9) . ? C25 C26 1.527(8) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 O26 1.435(7) . ? C26 C29 1.530(8) . ? O26 C27 1.437(7) . ? C27 C28 1.557(8) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C33 1.504(8) . ? C28 H28A 0.9800 . ? C29 C30 1.519(9) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.380(8) . ? C33 C38 1.409(8) . ? C34 C35 1.378(8) . ? C34 H34A 0.9300 . ? C35 C36 1.383(9) . ? C35 H35A 0.9300 . ? C36 C37 1.373(9) . ? C36 H36A 0.9300 . ? C37 C38 1.372(8) . ? C37 H37A 0.9300 . ? C38 H38A 0.9300 . ? S41 C43 1.735(7) . ? S41 C51 1.787(7) . ? S41 C52 1.798(6) . ? N41 C42 1.372(7) . ? N41 C48 1.473(7) . ? N41 C46 1.479(8) . ? C42 O42 1.250(7) . ? C42 C43 1.445(8) . ? C43 C44 1.432(9) . ? C44 O44 1.256(8) . ? C44 C45 1.503(8) . ? C45 C46 1.510(8) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 O46 1.425(7) . ? C46 C49 1.531(8) . ? O46 C47 1.433(7) . ? C47 C48 1.515(8) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 C53 1.497(8) . ? C48 H48A 0.9800 . ? C49 C50 1.525(8) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 0.9600 . ? C51 H51A 0.9600 . ? C51 H51B 0.9600 . ? C51 H51C 0.9600 . ? C52 H52A 0.9600 . ? C52 H52B 0.9600 . ? C52 H52C 0.9600 . ? C53 C54 1.380(9) . ? C53 C58 1.398(8) . ? C54 C55 1.396(10) . ? C54 H54A 0.9300 . ? C55 C56 1.403(10) . ? C55 H55A 0.9300 . ? C56 C57 1.335(10) . ? C56 H56A 0.9300 . ? C57 C58 1.402(9) . ? C57 H57A 0.9300 . ? C58 H58A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 S1 C11 106.8(4) . . ? C3 S1 C12 104.6(3) . . ? C11 S1 C12 100.7(3) . . ? C2 N1 C8 124.7(6) . . ? C2 N1 C6 122.3(6) . . ? C8 N1 C6 112.3(5) . . ? O2 C2 N1 117.7(6) . . ? O2 C2 C3 125.2(7) . . ? N1 C2 C3 117.0(6) . . ? C4 C3 C2 124.1(7) . . ? C4 C3 S1 121.8(5) . . ? C2 C3 S1 113.8(5) . . ? O4 C4 C3 124.7(7) . . ? O4 C4 C5 118.8(6) . . ? C3 C4 C5 116.2(6) . . ? C4 C5 C6 112.1(6) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? O6 C6 N1 102.3(5) . . ? O6 C6 C9 111.6(6) . . ? N1 C6 C9 112.2(5) . . ? O6 C6 C5 108.3(5) . . ? N1 C6 C5 109.0(6) . . ? C9 C6 C5 112.9(6) . . ? C6 O6 C7 105.0(5) . . ? O6 C7 C8 105.1(6) . . ? O6 C7 H7A 110.7 . . ? C8 C7 H7A 110.7 . . ? O6 C7 H7B 110.7 . . ? C8 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? N1 C8 C13 114.9(6) . . ? N1 C8 C7 99.3(5) . . ? C13 C8 C7 110.3(5) . . ? N1 C8 H8A 110.6 . . ? C13 C8 H8A 110.6 . . ? C7 C8 H8A 110.6 . . ? C10 C9 C6 115.2(6) . . ? C10 C9 H9A 108.5 . . ? C6 C9 H9A 108.5 . . ? C10 C9 H9B 108.5 . . ? C6 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? S1 C11 H11A 109.5 . . ? S1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? S1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? S1 C12 H12A 109.5 . . ? S1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? S1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 118.9(7) . . ? C14 C13 C8 119.9(7) . . ? C18 C13 C8 121.1(7) . . ? C15 C14 C13 121.6(7) . . ? C15 C14 H14A 119.2 . . ? C13 C14 H14A 119.2 . . ? C14 C15 C16 119.5(7) . . ? C14 C15 H15A 120.3 . . ? C16 C15 H15A 120.3 . . ? C17 C16 C15 120.1(8) . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C16 C17 C18 119.4(7) . . ? C16 C17 H17A 120.3 . . ? C18 C17 H17A 120.3 . . ? C17 C18 C13 120.5(7) . . ? C17 C18 H18A 119.7 . . ? C13 C18 H18A 119.7 . . ? C23 S21 C32 105.4(3) . . ? C23 S21 C31 106.4(3) . . ? C32 S21 C31 100.4(3) . . ? C22 N21 C28 123.2(6) . . ? C22 N21 C26 123.7(6) . . ? C28 N21 C26 112.2(5) . . ? O22 C22 N21 120.4(6) . . ? O22 C22 C23 124.5(6) . . ? N21 C22 C23 115.2(6) . . ? C24 C23 C22 123.8(6) . . ? C24 C23 S21 121.3(5) . . ? C22 C23 S21 114.8(5) . . ? O24 C24 C23 125.0(7) . . ? O24 C24 C25 118.9(6) . . ? C23 C24 C25 115.9(7) . . ? C24 C25 C26 111.8(5) . . ? C24 C25 H25A 109.3 . . ? C26 C25 H25A 109.3 . . ? C24 C25 H25B 109.3 . . ? C26 C25 H25B 109.3 . . ? H25A C25 H25B 107.9 . . ? O26 C26 N21 101.8(5) . . ? O26 C26 C25 109.5(5) . . ? N21 C26 C25 109.2(5) . . ? O26 C26 C29 110.2(5) . . ? N21 C26 C29 110.6(5) . . ? C25 C26 C29 114.7(6) . . ? C26 O26 C27 106.0(4) . . ? O26 C27 C28 102.3(5) . . ? O26 C27 H27A 111.3 . . ? C28 C27 H27A 111.3 . . ? O26 C27 H27B 111.3 . . ? C28 C27 H27B 111.3 . . ? H27A C27 H27B 109.2 . . ? N21 C28 C33 115.4(5) . . ? N21 C28 C27 99.5(5) . . ? C33 C28 C27 111.4(5) . . ? N21 C28 H28A 110.0 . . ? C33 C28 H28A 110.0 . . ? C27 C28 H28A 110.0 . . ? C30 C29 C26 113.4(6) . . ? C30 C29 H29A 108.9 . . ? C26 C29 H29A 108.9 . . ? C30 C29 H29B 108.9 . . ? C26 C29 H29B 108.9 . . ? H29A C29 H29B 107.7 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? S21 C31 H31A 109.5 . . ? S21 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? S21 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? S21 C32 H32A 109.5 . . ? S21 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? S21 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 C38 117.6(7) . . ? C34 C33 C28 120.4(6) . . ? C38 C33 C28 121.8(7) . . ? C35 C34 C33 122.1(7) . . ? C35 C34 H34A 119.0 . . ? C33 C34 H34A 119.0 . . ? C34 C35 C36 119.4(8) . . ? C34 C35 H35A 120.3 . . ? C36 C35 H35A 120.3 . . ? C37 C36 C35 119.7(7) . . ? C37 C36 H36A 120.2 . . ? C35 C36 H36A 120.2 . . ? C38 C37 C36 121.0(7) . . ? C38 C37 H37A 119.5 . . ? C36 C37 H37A 119.5 . . ? C37 C38 C33 120.3(7) . . ? C37 C38 H38A 119.9 . . ? C33 C38 H38A 119.9 . . ? C43 S41 C51 107.6(3) . . ? C43 S41 C52 105.2(3) . . ? C51 S41 C52 100.3(3) . . ? C42 N41 C48 124.5(6) . . ? C42 N41 C46 123.9(6) . . ? C48 N41 C46 111.3(5) . . ? O42 C42 N41 120.3(6) . . ? O42 C42 C43 125.5(6) . . ? N41 C42 C43 114.2(6) . . ? C44 C43 C42 124.2(6) . . ? C44 C43 S41 120.9(5) . . ? C42 C43 S41 114.8(5) . . ? O44 C44 C43 123.7(7) . . ? O44 C44 C45 120.8(6) . . ? C43 C44 C45 115.4(7) . . ? C44 C45 C46 111.2(5) . . ? C44 C45 H45A 109.4 . . ? C46 C45 H45A 109.4 . . ? C44 C45 H45B 109.4 . . ? C46 C45 H45B 109.4 . . ? H45A C45 H45B 108.0 . . ? O46 C46 N41 101.6(5) . . ? O46 C46 C45 110.6(5) . . ? N41 C46 C45 109.3(6) . . ? O46 C46 C49 110.3(6) . . ? N41 C46 C49 111.2(5) . . ? C45 C46 C49 113.3(6) . . ? C46 O46 C47 105.0(5) . . ? O46 C47 C48 105.0(5) . . ? O46 C47 H47A 110.8 . . ? C48 C47 H47A 110.8 . . ? O46 C47 H47B 110.8 . . ? C48 C47 H47B 110.8 . . ? H47A C47 H47B 108.8 . . ? N41 C48 C53 114.6(5) . . ? N41 C48 C47 99.3(5) . . ? C53 C48 C47 111.6(5) . . ? N41 C48 H48A 110.3 . . ? C53 C48 H48A 110.3 . . ? C47 C48 H48A 110.3 . . ? C50 C49 C46 112.4(5) . . ? C50 C49 H49A 109.1 . . ? C46 C49 H49A 109.1 . . ? C50 C49 H49B 109.1 . . ? C46 C49 H49B 109.1 . . ? H49A C49 H49B 107.9 . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? S41 C51 H51A 109.5 . . ? S41 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? S41 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? S41 C52 H52A 109.5 . . ? S41 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? S41 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C54 C53 C58 118.8(7) . . ? C54 C53 C48 119.0(7) . . ? C58 C53 C48 122.2(7) . . ? C53 C54 C55 122.1(8) . . ? C53 C54 H54A 119.0 . . ? C55 C54 H54A 119.0 . . ? C54 C55 C56 117.9(9) . . ? C54 C55 H55A 121.0 . . ? C56 C55 H55A 121.0 . . ? C57 C56 C55 120.3(10) . . ? C57 C56 H56A 119.8 . . ? C55 C56 H56A 119.8 . . ? C56 C57 C58 122.4(8) . . ? C56 C57 H57A 118.8 . . ? C58 C57 H57A 118.8 . . ? C53 C58 C57 118.5(7) . . ? C53 C58 H58A 120.7 . . ? C57 C58 H58A 120.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C2 O2 -15.2(9) . . . . ? C6 N1 C2 O2 175.0(5) . . . . ? C8 N1 C2 C3 161.6(6) . . . . ? C6 N1 C2 C3 -8.1(9) . . . . ? O2 C2 C3 C4 162.6(6) . . . . ? N1 C2 C3 C4 -13.9(9) . . . . ? O2 C2 C3 S1 -10.4(9) . . . . ? N1 C2 C3 S1 173.1(5) . . . . ? C11 S1 C3 C4 51.9(6) . . . . ? C12 S1 C3 C4 -54.3(6) . . . . ? C11 S1 C3 C2 -134.9(5) . . . . ? C12 S1 C3 C2 118.9(5) . . . . ? C2 C3 C4 O4 -173.9(7) . . . . ? S1 C3 C4 O4 -1.4(10) . . . . ? C2 C3 C4 C5 0.2(9) . . . . ? S1 C3 C4 C5 172.6(5) . . . . ? O4 C4 C5 C6 -153.3(6) . . . . ? C3 C4 C5 C6 32.3(8) . . . . ? C2 N1 C6 O6 153.8(5) . . . . ? C8 N1 C6 O6 -17.1(7) . . . . ? C2 N1 C6 C9 -86.5(7) . . . . ? C8 N1 C6 C9 102.6(7) . . . . ? C2 N1 C6 C5 39.2(8) . . . . ? C8 N1 C6 C5 -131.7(5) . . . . ? C4 C5 C6 O6 -160.0(5) . . . . ? C4 C5 C6 N1 -49.4(7) . . . . ? C4 C5 C6 C9 75.9(7) . . . . ? N1 C6 O6 C7 35.3(6) . . . . ? C9 C6 O6 C7 -84.8(6) . . . . ? C5 C6 O6 C7 150.4(5) . . . . ? C6 O6 C7 C8 -41.2(7) . . . . ? C2 N1 C8 C13 -59.8(8) . . . . ? C6 N1 C8 C13 110.8(6) . . . . ? C2 N1 C8 C7 -177.4(6) . . . . ? C6 N1 C8 C7 -6.8(7) . . . . ? O6 C7 C8 N1 28.4(6) . . . . ? O6 C7 C8 C13 -92.6(7) . . . . ? O6 C6 C9 C10 -53.5(9) . . . . ? N1 C6 C9 C10 -167.6(7) . . . . ? C5 C6 C9 C10 68.8(9) . . . . ? N1 C8 C13 C14 160.8(6) . . . . ? C7 C8 C13 C14 -87.9(8) . . . . ? N1 C8 C13 C18 -22.5(9) . . . . ? C7 C8 C13 C18 88.7(8) . . . . ? C18 C13 C14 C15 -1.7(11) . . . . ? C8 C13 C14 C15 175.1(7) . . . . ? C13 C14 C15 C16 1.1(12) . . . . ? C14 C15 C16 C17 -0.6(11) . . . . ? C15 C16 C17 C18 0.6(11) . . . . ? C16 C17 C18 C13 -1.1(10) . . . . ? C14 C13 C18 C17 1.7(10) . . . . ? C8 C13 C18 C17 -175.0(6) . . . . ? C28 N21 C22 O22 -17.7(9) . . . . ? C26 N21 C22 O22 174.0(5) . . . . ? C28 N21 C22 C23 160.3(5) . . . . ? C26 N21 C22 C23 -7.9(9) . . . . ? O22 C22 C23 C24 163.7(6) . . . . ? N21 C22 C23 C24 -14.3(9) . . . . ? O22 C22 C23 S21 -13.8(8) . . . . ? N21 C22 C23 S21 168.2(4) . . . . ? C32 S21 C23 C24 -48.6(6) . . . . ? C31 S21 C23 C24 57.6(6) . . . . ? C32 S21 C23 C22 129.0(5) . . . . ? C31 S21 C23 C22 -124.9(5) . . . . ? C22 C23 C24 O24 -175.6(6) . . . . ? S21 C23 C24 O24 1.7(9) . . . . ? C22 C23 C24 C25 0.0(9) . . . . ? S21 C23 C24 C25 177.4(5) . . . . ? O24 C24 C25 C26 -150.8(6) . . . . ? C23 C24 C25 C26 33.3(8) . . . . ? C22 N21 C26 O26 156.0(5) . . . . ? C28 N21 C26 O26 -13.4(6) . . . . ? C22 N21 C26 C25 40.2(8) . . . . ? C28 N21 C26 C25 -129.1(5) . . . . ? C22 N21 C26 C29 -86.9(7) . . . . ? C28 N21 C26 C29 103.7(6) . . . . ? C24 C25 C26 O26 -161.5(5) . . . . ? C24 C25 C26 N21 -50.8(8) . . . . ? C24 C25 C26 C29 74.1(8) . . . . ? N21 C26 O26 C27 35.7(6) . . . . ? C25 C26 O26 C27 151.3(6) . . . . ? C29 C26 O26 C27 -81.7(6) . . . . ? C26 O26 C27 C28 -44.0(6) . . . . ? C22 N21 C28 C33 -62.0(8) . . . . ? C26 N21 C28 C33 107.4(6) . . . . ? C22 N21 C28 C27 178.6(5) . . . . ? C26 N21 C28 C27 -11.9(6) . . . . ? O26 C27 C28 N21 32.9(6) . . . . ? O26 C27 C28 C33 -89.4(6) . . . . ? O26 C26 C29 C30 -59.1(8) . . . . ? N21 C26 C29 C30 -171.0(6) . . . . ? C25 C26 C29 C30 65.0(8) . . . . ? N21 C28 C33 C34 165.3(6) . . . . ? C27 C28 C33 C34 -82.2(7) . . . . ? N21 C28 C33 C38 -19.5(8) . . . . ? C27 C28 C33 C38 93.1(7) . . . . ? C38 C33 C34 C35 1.6(9) . . . . ? C28 C33 C34 C35 177.1(6) . . . . ? C33 C34 C35 C36 -0.5(10) . . . . ? C34 C35 C36 C37 -0.9(11) . . . . ? C35 C36 C37 C38 1.1(11) . . . . ? C36 C37 C38 C33 0.0(10) . . . . ? C34 C33 C38 C37 -1.4(9) . . . . ? C28 C33 C38 C37 -176.8(6) . . . . ? C48 N41 C42 O42 -12.7(9) . . . . ? C46 N41 C42 O42 173.3(5) . . . . ? C48 N41 C42 C43 167.3(5) . . . . ? C46 N41 C42 C43 -6.7(9) . . . . ? O42 C42 C43 C44 165.9(6) . . . . ? N41 C42 C43 C44 -14.1(9) . . . . ? O42 C42 C43 S41 -10.9(8) . . . . ? N41 C42 C43 S41 169.2(5) . . . . ? C51 S41 C43 C44 54.9(6) . . . . ? C52 S41 C43 C44 -51.4(6) . . . . ? C51 S41 C43 C42 -128.2(5) . . . . ? C52 S41 C43 C42 125.5(5) . . . . ? C42 C43 C44 O44 -179.4(7) . . . . ? S41 C43 C44 O44 -2.8(9) . . . . ? C42 C43 C44 C45 -2.1(9) . . . . ? S41 C43 C44 C45 174.5(5) . . . . ? O44 C44 C45 C46 -146.3(6) . . . . ? C43 C44 C45 C46 36.3(8) . . . . ? C42 N41 C46 O46 157.1(5) . . . . ? C48 N41 C46 O46 -17.6(6) . . . . ? C42 N41 C46 C45 40.2(8) . . . . ? C48 N41 C46 C45 -134.5(5) . . . . ? C42 N41 C46 C49 -85.6(7) . . . . ? C48 N41 C46 C49 99.7(6) . . . . ? C44 C45 C46 O46 -163.7(5) . . . . ? C44 C45 C46 N41 -52.7(7) . . . . ? C44 C45 C46 C49 71.9(8) . . . . ? N41 C46 O46 C47 37.0(6) . . . . ? C45 C46 O46 C47 152.9(5) . . . . ? C49 C46 O46 C47 -81.0(6) . . . . ? C46 O46 C47 C48 -43.9(6) . . . . ? C42 N41 C48 C53 -63.2(8) . . . . ? C46 N41 C48 C53 111.5(6) . . . . ? C42 N41 C48 C47 177.8(6) . . . . ? C46 N41 C48 C47 -7.5(6) . . . . ? O46 C47 C48 N41 30.2(6) . . . . ? O46 C47 C48 C53 -91.0(6) . . . . ? O46 C46 C49 C50 -57.8(7) . . . . ? N41 C46 C49 C50 -169.7(6) . . . . ? C45 C46 C49 C50 66.8(8) . . . . ? N41 C48 C53 C54 161.6(6) . . . . ? C47 C48 C53 C54 -86.5(7) . . . . ? N41 C48 C53 C58 -22.3(9) . . . . ? C47 C48 C53 C58 89.6(7) . . . . ? C58 C53 C54 C55 -0.3(11) . . . . ? C48 C53 C54 C55 175.9(7) . . . . ? C53 C54 C55 C56 0.4(12) . . . . ? C54 C55 C56 C57 -0.9(13) . . . . ? C55 C56 C57 C58 1.3(13) . . . . ? C54 C53 C58 C57 0.7(10) . . . . ? C48 C53 C58 C57 -175.4(6) . . . . ? C56 C57 C58 C53 -1.2(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C7 H7B O6 0.97 2.53 3.356(8) 143.4 4_567 yes C11 H11B O4 0.96 2.52 3.391(8) 150.5 1_655 yes C11 H11C O4 0.96 2.44 3.090(8) 125.2 . yes C12 H12B O4 0.96 2.45 3.118(8) 126.8 . yes C31 H31B O24 0.96 2.44 3.294(8) 148.0 1_455 yes C31 H31C O24 0.96 2.58 3.217(8) 124.4 . yes C32 H32B O24 0.96 2.28 3.001(8) 131.2 . yes C51 H51B O44 0.96 2.40 3.264(8) 149.2 1_455 yes C51 H51C O44 0.96 2.52 3.137(8) 121.9 . yes C52 H52B O44 0.96 2.42 3.067(8) 124.2 . yes _refine_diff_density_max 0.148 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.037 _shelx_res_file ; TITL enr-410-1_a.res in P2(1)2(1)2(1) ENR-410-1.res created by SHELXL-2018/3 at 19:00:17 on 20-Oct-2019 CELL 0.56083 5.4670 27.8275 32.8425 90.000 90.000 90.000 ZERR 12.00 0.0002 0.0012 0.0020 0.000 0.000 0.000 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O S UNIT 204 252 12 36 12 TEMP 22 SIZE 0.458 0.092 0.069 L.S. 14 PLAN 20 BOND $H CONF EQIV $1 x+1/2, -y+3/2, -z+2 EQIV $2 x+1, y, z EQIV $3 x-1, y, z HTAB C7 O6_$1 HTAB C11 O4_$2 HTAB C11 O4 HTAB C12 O4 HTAB C31 O24_$3 HTAB C31 O24 HTAB C32 O24 HTAB C51 O44_$3 HTAB C51 O44 HTAB C52 O44 LIST 4 FMAP 2 ACTA WGHT 0.011400 EXTI 0.000601 FVAR 0.22979 S1 5 0.858552 0.526110 0.890920 11.00000 0.06133 0.06593 = 0.07240 -0.01558 -0.00203 0.00477 N1 3 0.811705 0.635464 0.965664 11.00000 0.04932 0.04114 = 0.05618 -0.00288 -0.00573 0.00046 C2 1 0.864504 0.590629 0.949324 11.00000 0.04821 0.04840 = 0.06421 -0.00286 0.00107 0.00271 O2 4 0.995346 0.562573 0.970138 11.00000 0.07015 0.05754 = 0.07857 -0.00549 -0.01427 0.01048 C3 1 0.756376 0.579304 0.911572 11.00000 0.04895 0.04761 = 0.05728 -0.01474 -0.00376 0.00695 C4 1 0.562785 0.605417 0.894013 11.00000 0.05717 0.05443 = 0.06523 0.00402 -0.00052 0.00244 O4 4 0.450645 0.593418 0.861836 11.00000 0.07808 0.10346 = 0.07433 -0.00660 -0.02216 0.00560 C5 1 0.470971 0.648053 0.918062 11.00000 0.05119 0.06423 = 0.07560 0.01823 -0.00778 0.00522 AFIX 23 H5A 2 0.343508 0.637515 0.936566 11.00000 -1.20000 H5B 2 0.399879 0.671310 0.899516 11.00000 -1.20000 AFIX 0 C6 1 0.677452 0.672442 0.942737 11.00000 0.04990 0.05461 = 0.06070 0.00649 0.00414 0.01279 O6 4 0.568641 0.700049 0.974311 11.00000 0.08161 0.04984 = 0.08583 -0.00009 0.01301 0.01293 C7 1 0.744878 0.700006 1.006627 11.00000 0.08108 0.05734 = 0.09210 -0.00669 0.00517 -0.01237 AFIX 23 H7A 2 0.668340 0.708356 1.032316 11.00000 -1.20000 H7B 2 0.875000 0.722788 1.001101 11.00000 -1.20000 AFIX 0 C8 1 0.845125 0.648442 1.007903 11.00000 0.05194 0.03782 = 0.06827 -0.00951 -0.00374 0.00066 AFIX 13 H8A 2 1.019210 0.648476 1.015019 11.00000 -1.20000 AFIX 0 C9 1 0.845379 0.702687 0.916559 11.00000 0.06850 0.05062 = 0.08688 0.01187 0.01649 0.00902 AFIX 23 H9A 2 0.986228 0.711878 0.932744 11.00000 -1.20000 H9B 2 0.904088 0.683028 0.894213 11.00000 -1.20000 AFIX 0 C10 1 0.732529 0.747193 0.899301 11.00000 0.11819 0.10267 = 0.18856 0.09677 0.04161 0.03063 AFIX 137 H10A 2 0.851982 0.764205 0.883450 11.00000 -1.50000 H10B 2 0.676454 0.767363 0.921100 11.00000 -1.50000 H10C 2 0.596697 0.738585 0.882272 11.00000 -1.50000 AFIX 0 C11 1 0.918105 0.537338 0.838557 11.00000 0.09460 0.08815 = 0.07388 -0.01493 0.02107 -0.01101 AFIX 137 H11A 2 0.959929 0.507744 0.825245 11.00000 -1.50000 H11B 2 1.051625 0.559558 0.836112 11.00000 -1.50000 H11C 2 0.774917 0.550775 0.826039 11.00000 -1.50000 AFIX 0 C12 1 0.587198 0.488849 0.887203 11.00000 0.05459 0.06094 = 0.10807 -0.01358 0.00343 -0.01114 AFIX 137 H12A 2 0.622898 0.460935 0.871088 11.00000 -1.50000 H12B 2 0.457906 0.506826 0.874585 11.00000 -1.50000 H12C 2 0.537188 0.479068 0.913969 11.00000 -1.50000 AFIX 0 C13 1 0.701099 0.618548 1.037819 11.00000 0.05039 0.03922 = 0.06444 -0.00395 0.00120 0.00212 C14 1 0.768616 0.617440 1.077965 11.00000 0.06805 0.07690 = 0.06298 -0.00738 -0.00007 -0.01341 AFIX 43 H14A 2 0.910555 0.633227 1.086007 11.00000 -1.20000 AFIX 0 C15 1 0.632407 0.593683 1.106529 11.00000 0.09413 0.09552 = 0.05900 -0.01530 -0.00912 -0.00351 AFIX 43 H15A 2 0.679982 0.593839 1.133716 11.00000 -1.20000 AFIX 0 C16 1 0.421880 0.569256 1.094574 11.00000 0.09119 0.06693 = 0.07607 0.01626 0.01708 0.00605 AFIX 43 H16A 2 0.329153 0.552792 1.113784 11.00000 -1.20000 AFIX 0 C17 1 0.350732 0.569467 1.054216 11.00000 0.05846 0.06086 = 0.08487 0.00877 0.00394 -0.00792 AFIX 43 H17A 2 0.209499 0.553443 1.046165 11.00000 -1.20000 AFIX 0 C18 1 0.491794 0.593785 1.025816 11.00000 0.05710 0.05654 = 0.05942 0.01457 0.00106 0.00721 AFIX 43 H18A 2 0.446270 0.593558 0.998533 11.00000 -1.20000 AFIX 0 S21 5 0.673713 0.510838 0.726893 11.00000 0.06145 0.05241 = 0.06798 0.00882 0.00502 -0.00539 N21 3 0.667571 0.379587 0.771355 11.00000 0.04781 0.04426 = 0.05643 0.00282 0.01381 0.00722 C22 1 0.626137 0.428194 0.768357 11.00000 0.04267 0.04139 = 0.05836 -0.00006 -0.00703 -0.00327 O22 4 0.482167 0.448384 0.792004 11.00000 0.05903 0.04718 = 0.06852 -0.00013 0.01388 0.00414 C23 1 0.767366 0.452731 0.737138 11.00000 0.04841 0.03586 = 0.06948 0.00954 0.00266 0.00854 C24 1 0.971898 0.432401 0.717396 11.00000 0.05521 0.05517 = 0.06108 -0.00827 -0.00222 0.00441 O24 4 1.105961 0.453977 0.691950 11.00000 0.06977 0.07624 = 0.06345 0.00181 0.02006 -0.00914 C25 1 1.041134 0.381879 0.730596 11.00000 0.05059 0.06944 = 0.07124 -0.00437 0.00637 0.00738 AFIX 23 H25A 2 1.151175 0.383689 0.753713 11.00000 -1.20000 H25B 2 1.127023 0.365974 0.708544 11.00000 -1.20000 AFIX 0 C26 1 0.816732 0.352239 0.742266 11.00000 0.04987 0.04547 = 0.06139 -0.00679 -0.00411 -0.00040 O26 4 0.891136 0.311808 0.766370 11.00000 0.06184 0.04681 = 0.07535 0.00369 -0.00246 0.01225 C27 1 0.687372 0.300846 0.792411 11.00000 0.05474 0.05229 = 0.07180 0.01004 0.00284 -0.01021 AFIX 23 H27A 2 0.736678 0.280609 0.815015 11.00000 -1.20000 H27B 2 0.557202 0.285062 0.777446 11.00000 -1.20000 AFIX 0 C28 1 0.607085 0.351566 0.807355 11.00000 0.04515 0.04213 = 0.05986 -0.00335 -0.00158 0.00582 AFIX 13 H28A 2 0.430027 0.352140 0.811989 11.00000 -1.20000 AFIX 0 C29 1 0.661138 0.335462 0.706228 11.00000 0.06866 0.07213 = 0.06203 -0.01621 0.00112 -0.00033 AFIX 23 H29A 2 0.514193 0.320189 0.716550 11.00000 -1.20000 H29B 2 0.611499 0.363306 0.690498 11.00000 -1.20000 AFIX 0 C30 1 0.793243 0.300483 0.678339 11.00000 0.11139 0.09795 = 0.10071 -0.03974 0.00367 0.02245 AFIX 137 H30A 2 0.683337 0.289717 0.657446 11.00000 -1.50000 H30B 2 0.848907 0.273389 0.693880 11.00000 -1.50000 H30C 2 0.930964 0.316240 0.666067 11.00000 -1.50000 AFIX 0 C31 1 0.614326 0.513499 0.673074 11.00000 0.08753 0.06740 = 0.06530 0.01243 -0.01601 -0.01730 AFIX 137 H31A 2 0.589445 0.546322 0.665085 11.00000 -1.50000 H31B 2 0.470443 0.495111 0.666906 11.00000 -1.50000 H31C 2 0.751393 0.500484 0.658506 11.00000 -1.50000 AFIX 0 C32 1 0.945150 0.546818 0.729936 11.00000 0.07481 0.06313 = 0.08481 -0.00731 -0.00425 -0.02744 AFIX 137 H32A 2 0.927132 0.574659 0.712937 11.00000 -1.50000 H32B 2 1.083054 0.528320 0.720890 11.00000 -1.50000 H32C 2 0.970604 0.556739 0.757609 11.00000 -1.50000 AFIX 0 C33 1 0.739744 0.365750 0.845643 11.00000 0.05135 0.02982 = 0.06292 -0.00428 -0.00163 0.00588 C34 1 0.659536 0.349635 0.883067 11.00000 0.06483 0.04353 = 0.07280 0.00296 -0.00789 -0.00063 AFIX 43 H34A 2 0.518112 0.331124 0.884345 11.00000 -1.20000 AFIX 0 C35 1 0.782443 0.360115 0.918601 11.00000 0.08266 0.05161 = 0.06443 0.00225 -0.00576 -0.00187 AFIX 43 H35A 2 0.723731 0.348993 0.943451 11.00000 -1.20000 AFIX 0 C36 1 0.993985 0.387334 0.916978 11.00000 0.07308 0.06194 = 0.08077 -0.01401 -0.02063 0.00448 AFIX 43 H36A 2 1.077198 0.395023 0.940801 11.00000 -1.20000 AFIX 0 C37 1 1.080481 0.402940 0.880019 11.00000 0.05689 0.07343 = 0.08963 -0.00097 -0.01364 -0.01446 AFIX 43 H37A 2 1.224287 0.420750 0.878970 11.00000 -1.20000 AFIX 0 C38 1 0.957969 0.392657 0.844612 11.00000 0.04499 0.04836 = 0.06802 0.00102 0.00045 -0.00329 AFIX 43 H38A 2 1.019209 0.403489 0.819839 11.00000 -1.20000 AFIX 0 S41 5 1.089108 0.055033 0.939077 11.00000 0.05663 0.05217 = 0.07584 0.00960 -0.00601 -0.00281 N41 3 1.136998 0.175831 0.877955 11.00000 0.04996 0.04729 = 0.05785 0.00328 -0.00967 -0.00438 C42 1 1.081108 0.128828 0.886527 11.00000 0.04706 0.04297 = 0.05906 0.00924 -0.00289 0.00519 O42 4 0.940008 0.105763 0.863815 11.00000 0.06341 0.05311 = 0.06768 -0.00245 -0.01634 -0.00361 C43 1 1.197940 0.110329 0.922746 11.00000 0.05734 0.04010 = 0.06659 0.01202 0.00115 -0.01490 C44 1 1.397198 0.133442 0.943191 11.00000 0.05266 0.04657 = 0.07929 -0.00415 -0.00407 -0.00500 O44 4 1.498787 0.116875 0.974470 11.00000 0.06270 0.06966 = 0.07784 0.01018 -0.02681 0.00012 C45 1 1.488267 0.178841 0.923592 11.00000 0.04402 0.05812 = 0.07278 -0.00121 -0.00399 0.00226 AFIX 23 H45A 2 1.605308 0.170835 0.902457 11.00000 -1.20000 H45B 2 1.571364 0.198324 0.943803 11.00000 -1.20000 AFIX 0 C46 1 1.280410 0.207286 0.905286 11.00000 0.04752 0.05116 = 0.05698 -0.00253 -0.00119 -0.00339 O46 4 1.371090 0.242329 0.877471 11.00000 0.05659 0.05491 = 0.06239 0.00598 0.00086 -0.00917 C47 1 1.176028 0.249838 0.849035 11.00000 0.07114 0.04654 = 0.07802 0.00514 -0.00608 -0.00002 AFIX 23 H47A 2 1.235446 0.265795 0.824711 11.00000 -1.20000 H47B 2 1.047627 0.269256 0.861067 11.00000 -1.20000 AFIX 0 C48 1 1.082520 0.199952 0.839059 11.00000 0.04822 0.04266 = 0.06760 0.01027 -0.00286 0.00584 AFIX 13 H48A 2 0.905572 0.200732 0.834330 11.00000 -1.20000 AFIX 0 C49 1 1.116545 0.231133 0.937235 11.00000 0.05942 0.05046 = 0.06612 0.00411 0.00018 -0.00069 AFIX 23 H49A 2 0.974832 0.244910 0.923835 11.00000 -1.20000 H49B 2 1.058990 0.206889 0.956170 11.00000 -1.20000 AFIX 0 C50 1 1.249498 0.270447 0.960834 11.00000 0.08721 0.06274 = 0.07866 -0.01602 -0.00381 0.00317 AFIX 137 H50A 2 1.131853 0.291253 0.973488 11.00000 -1.50000 H50B 2 1.349552 0.288753 0.942492 11.00000 -1.50000 H50C 2 1.350780 0.256081 0.981377 11.00000 -1.50000 AFIX 0 C51 1 1.012361 0.060660 0.991753 11.00000 0.08449 0.08136 = 0.08289 0.01788 0.02644 0.00805 AFIX 137 H51A 2 0.953783 0.030365 1.001776 11.00000 -1.50000 H51B 2 0.887186 0.084561 0.994931 11.00000 -1.50000 H51C 2 1.154886 0.070075 1.006850 11.00000 -1.50000 AFIX 0 C52 1 1.354878 0.017225 0.942565 11.00000 0.06151 0.05718 = 0.09698 0.00735 -0.00709 0.02390 AFIX 137 H52A 2 1.308039 -0.013840 0.952605 11.00000 -1.50000 H52B 2 1.471113 0.031465 0.960854 11.00000 -1.50000 H52C 2 1.427420 0.013859 0.916099 11.00000 -1.50000 AFIX 0 C53 1 1.211237 0.179142 0.802914 11.00000 0.05463 0.04193 = 0.05494 -0.00315 0.00398 -0.01074 C54 1 1.123746 0.189239 0.764453 11.00000 0.08645 0.07179 = 0.06162 -0.00194 -0.00324 -0.00257 AFIX 43 H54A 2 0.980629 0.207043 0.761859 11.00000 -1.20000 AFIX 0 C55 1 1.243175 0.173585 0.729308 11.00000 0.13636 0.08910 = 0.08153 -0.00450 0.01084 0.00563 AFIX 43 H55A 2 1.182331 0.180870 0.703595 11.00000 -1.20000 AFIX 0 C56 1 1.457816 0.146524 0.733980 11.00000 0.10489 0.08896 = 0.09095 -0.00520 0.03188 -0.00412 AFIX 43 H56A 2 1.540051 0.135220 0.711116 11.00000 -1.20000 AFIX 0 C57 1 1.544618 0.136919 0.771101 11.00000 0.08047 0.06343 = 0.11949 -0.00092 0.01432 0.00650 AFIX 43 H57A 2 1.689077 0.119490 0.773450 11.00000 -1.20000 AFIX 0 C58 1 1.425805 0.152165 0.806676 11.00000 0.05357 0.06008 = 0.07765 -0.01394 0.00916 0.00079 AFIX 43 H58A 2 1.488342 0.144501 0.832197 11.00000 -1.20000 AFIX 0 HKLF 4 REM enr-410-1_a.res in P2(1)2(1)2(1) REM wR2 = 0.0874, GooF = S = 0.647, Restrained GooF = 0.647 for all data REM R1 = 0.0430 for 3129 Fo > 4sig(Fo) and 0.1652 for all 9490 data REM 605 parameters refined using 0 restraints END WGHT 0.0057 0.0000 REM Highest difference peak 0.148, deepest hole -0.205, 1-sigma level 0.037 Q1 1 0.8200 0.4790 0.6893 11.00000 0.05 0.15 Q2 1 0.8964 0.5667 1.1185 11.00000 0.05 0.14 Q3 1 0.6724 0.5755 0.8267 11.00000 0.05 0.14 Q4 1 1.2562 0.0894 0.9705 11.00000 0.05 0.14 Q5 1 1.0833 0.5120 0.7698 11.00000 0.05 0.14 Q6 1 1.0282 0.0489 1.0303 11.00000 0.05 0.13 Q7 1 0.7512 0.6943 0.8600 11.00000 0.05 0.13 Q8 1 0.6711 0.3511 0.8295 11.00000 0.05 0.13 Q9 1 0.8855 0.0311 0.9134 11.00000 0.05 0.13 Q10 1 1.2075 0.1902 0.8916 11.00000 0.05 0.13 Q11 1 0.8975 -0.0008 1.0018 11.00000 0.05 0.13 Q12 1 1.5965 0.0488 0.9384 11.00000 0.05 0.13 Q13 1 0.8677 0.5751 1.0716 11.00000 0.05 0.13 Q14 1 0.7554 0.3695 0.7588 11.00000 0.05 0.13 Q15 1 1.1669 0.1189 0.8306 11.00000 0.05 0.12 Q16 1 0.6779 0.5602 0.8594 11.00000 0.05 0.12 Q17 1 1.0506 0.5646 0.9149 11.00000 0.05 0.12 Q18 1 0.9135 0.3608 0.7349 11.00000 0.05 0.12 Q19 1 0.8856 0.3520 0.7931 11.00000 0.05 0.12 Q20 1 0.8960 0.1031 0.9179 11.00000 0.05 0.12 ; _shelx_res_checksum 66331 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_22ab _database_code_depnum_ccdc_archive 'CCDC 2125365' loop_ _audit_author_name _audit_author_address 'Sylvain Bernes' ;Instituto de Fisica, BUAP, Puebla Mexico ; _audit_update_record ; 2021-11-30 deposited with the CCDC. 2022-01-21 downloaded from the CCDC. ; # Clave Lab. : ENR-101 # Clave IF-UAP: ENR101 # Solicitud: 97 # Firma en la Solicitud: Dr. Joel L. Teran, ICUAP # Clave datos : ... \BUAP\Sylvain\ENR101\40mm_2\ _database_code_CAS ? _database_code_CSD ? _audit_creation_method SHELXL-2018/1 _shelx_SHELXL_version_number 2018/1 _audit_creation_date 2018-04-18 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 N O3 S' _chemical_formula_sum 'C15 H17 N O3 S' _chemical_formula_weight 291.35 _chemical_absolute_configuration ad _chemical_optical_rotation ? _chemical_properties_physical ? _chemical_properties_biological ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.0826 0.0763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 1 _space_group_name_H-M_alt 'P 1' _space_group_name_Hall 'P 1' _shelx_space_group_comment ? loop_ _space_group_symop_operation_xyz 'x, y, z' _cell_length_a 6.0976(4) _cell_length_b 9.5728(8) _cell_length_c 12.3463(10) _cell_angle_alpha 99.389(7) _cell_angle_beta 90.433(6) _cell_angle_gamma 89.796(7) _cell_volume 710.99(10) _cell_formula_units_Z 2 _cell_measurement_temperature 243(1) _cell_measurement_reflns_used 10706 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 26.73 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_F_000 308 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.050 _exptl_absorpt_coefficient_mu 0.128 _shelx_estimated_absorpt_T_min 0.951 _shelx_estimated_absorpt_T_max 0.994 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5109 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'X-Area (Stoe & Cie, 2015)' _diffrn_ambient_temperature 243(1) _diffrn_ambient_environment air _diffrn_measurement_specimen_support 'Mitegen 50um' _diffrn_source 'Sealed X-ray tube' _diffrn_source_type 'Axo Astix-f Microfocus source' _diffrn_source_voltage 65 _diffrn_source_current 0.600 _diffrn_source_power 0.039 _diffrn_radiation_collimation '0.6 mm diameter' _diffrn_radiation_probe x-ray _diffrn_radiation_type AgK\a _diffrn_radiation_wavelength 0.56083 _diffrn_radiation_monochromator 'Graded multilayer mirror' _diffrn_radiation_polarisn_norm -90 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Stoe Stadivari' _diffrn_detector 'Reverse-biased silicon diode array' _diffrn_detector_type 'Dectris Pilatus 100K R' _diffrn_measurement_method '\w scans' _diffrn_measurement_details ; 1375 frames, 115 s/frame, 1 deg./frame, detector distance = 40 mm ; _diffrn_detector_area_resol_mean 5.81 _diffrn_reflns_number 17365 _diffrn_reflns_av_unetI/netI 0.1109 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.636 _diffrn_reflns_theta_max 19.999 _diffrn_reflns_theta_full 19.664 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.891 _diffrn_reflns_point_group_measured_fraction_full 0.890 _reflns_number_total 4804 _reflns_number_gt 2713 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.787 _reflns_Friedel_fraction_max 0.785 _reflns_Friedel_fraction_full 0.783 _reflns_special_details ? _computing_data_collection 'X-AREA (Stoe & Cie, 2015)' _computing_cell_refinement X-AREA _computing_data_reduction X-AREA _computing_structure_solution 'SHELXT-2014/5 (Sheldrick, 2015a)' _computing_structure_refinement 'SHELXL-2018/1 (Sheldrick, 2018)' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)' _computing_publication_material 'PublCif (Westrip, 2010)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0511P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 782 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.20(16) _refine_ls_number_reflns 4804 _refine_ls_number_parameters 375 _refine_ls_number_restraints 3 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1036 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1234 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.900 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.2728(3) 0.0994(2) 0.49990(16) 0.0589(6) Uani 1 1 d . . . . . O1 O -0.2041(10) 0.1155(7) 0.9067(5) 0.094(2) Uani 1 1 d . . . . . O2 O -0.1218(7) 0.2781(5) 0.5896(4) 0.0491(12) Uani 1 1 d . . . . . O3 O 0.3854(10) -0.0611(6) 0.6757(5) 0.0852(19) Uani 1 1 d . . . . . C2 C -0.3647(15) 0.2057(10) 0.8955(7) 0.076(3) Uani 1 1 d . . . . . H2A H -0.365769 0.281447 0.959287 0.091 Uiso 1 1 calc R U . . . H2B H -0.505724 0.156396 0.892495 0.091 Uiso 1 1 calc R U . . . C3 C -0.3357(11) 0.2706(7) 0.7898(6) 0.0453(17) Uani 1 1 d . . . . . H3A H -0.452370 0.236147 0.735966 0.054 Uiso 1 1 calc R U . . . N4 N -0.1270(9) 0.2053(7) 0.7545(5) 0.0544(17) Uani 1 1 d . . . . . C5 C -0.0443(10) 0.2021(7) 0.6509(6) 0.0413(16) Uani 1 1 d . . . . . C6 C 0.1372(11) 0.1071(8) 0.6239(6) 0.0437(18) Uani 1 1 d . . . . . C7 C 0.2211(13) 0.0152(8) 0.6943(6) 0.058(2) Uani 1 1 d . . . . . C8 C 0.0919(17) 0.0164(10) 0.7994(7) 0.086(3) Uani 1 1 d . . . . . H8A H -0.014677 -0.061038 0.786715 0.104 Uiso 0.55(3) 1 calc R U P A 1 H8B H 0.193701 -0.003968 0.856655 0.104 Uiso 0.55(3) 1 calc R U P A 1 H8C H 0.094497 -0.079553 0.817469 0.104 Uiso 0.45(3) 1 calc R U P A 2 H8D H 0.168253 0.078167 0.858863 0.104 Uiso 0.45(3) 1 calc R U P A 2 C8AA C -0.021(4) 0.142(3) 0.8398(17) 0.071(9) Uani 0.55(3) 1 d . . P A 1 H8AA H 0.079782 0.210981 0.882692 0.085 Uiso 0.55(3) 1 calc R U P A 1 C8AB C -0.123(3) 0.060(2) 0.7980(16) 0.035(6) Uani 0.45(3) 1 d . . P A 2 H8AB H -0.220452 -0.011976 0.756010 0.043 Uiso 0.45(3) 1 calc R U P A 2 C9 C -0.3335(10) 0.4299(7) 0.8115(5) 0.0390(16) Uani 1 1 d . . . . . C10 C -0.5180(12) 0.5033(9) 0.7833(6) 0.0552(19) Uani 1 1 d . . . . . H10A H -0.636568 0.451789 0.747987 0.066 Uiso 1 1 calc R U . . . C11 C -0.5314(17) 0.6457(11) 0.8051(8) 0.073(3) Uani 1 1 d . . . . . H11A H -0.657280 0.692437 0.784649 0.087 Uiso 1 1 calc R U . . . C12 C -0.362(2) 0.7213(11) 0.8568(9) 0.090(3) Uani 1 1 d . . . . . H12A H -0.371240 0.820574 0.872623 0.108 Uiso 1 1 calc R U . . . C13 C -0.1789(18) 0.6555(12) 0.8858(7) 0.075(3) Uani 1 1 d . . . . . H13A H -0.062482 0.709312 0.921004 0.090 Uiso 1 1 calc R U . . . C14 C -0.1619(12) 0.5077(10) 0.8636(6) 0.058(2) Uani 1 1 d . . . . . H14A H -0.035073 0.461999 0.884025 0.070 Uiso 1 1 calc R U . . . C15 C 0.0703(15) 0.0741(9) 0.3927(7) 0.074(3) Uani 1 1 d . . . . . H15A H 0.013375 -0.021532 0.384799 0.110 Uiso 1 1 calc R U . . . H15B H 0.136398 0.088851 0.324290 0.110 Uiso 1 1 calc R U . . . H15C H -0.048416 0.141280 0.411091 0.110 Uiso 1 1 calc R U . . . C16 C 0.3625(13) 0.2772(9) 0.4911(7) 0.069(2) Uani 1 1 d . . . . . H16A H 0.432323 0.318487 0.559672 0.104 Uiso 1 1 calc R U . . . H16B H 0.236884 0.334414 0.477284 0.104 Uiso 1 1 calc R U . . . H16C H 0.466318 0.274052 0.431598 0.104 Uiso 1 1 calc R U . . . S21 S 0.7602(3) 0.5936(2) 0.48196(16) 0.0575(6) Uani 1 1 d . . . . . O21 O 1.2533(10) 0.4325(6) 0.0799(4) 0.0708(16) Uani 1 1 d . . . . . O22 O 1.1493(7) 0.7380(5) 0.3913(4) 0.0496(12) Uani 1 1 d . . . . . O23 O 0.6543(10) 0.3577(7) 0.3060(5) 0.0851(19) Uani 1 1 d . . . . . C22 C 1.4067(16) 0.5402(9) 0.0848(8) 0.084(3) Uani 1 1 d . . . . . H22A H 1.388079 0.589418 0.021649 0.101 Uiso 1 1 calc R U . . . H22B H 1.555400 0.500718 0.082985 0.101 Uiso 1 1 calc R U . . . C23 C 1.3717(11) 0.6445(7) 0.1927(6) 0.0487(18) Uani 1 1 d . . . . . H23A H 1.494294 0.637465 0.244625 0.058 Uiso 1 1 calc R U . . . N24 N 1.1702(9) 0.5867(6) 0.2318(5) 0.0515(17) Uani 1 1 d . . . . . C25 C 1.0795(10) 0.6302(7) 0.3329(5) 0.0397(16) Uani 1 1 d . . . . . C26 C 0.9001(11) 0.5466(7) 0.3591(6) 0.0415(17) Uani 1 1 d . . . . . C27 C 0.8174(12) 0.4251(8) 0.2897(6) 0.0542(19) Uani 1 1 d . . . . . C28 C 0.9452(16) 0.3821(10) 0.1842(7) 0.081(3) Uani 1 1 d . . . . . H28A H 0.966079 0.279183 0.173667 0.097 Uiso 1 1 calc R U . . . H28B H 0.853460 0.402717 0.123193 0.097 Uiso 1 1 calc R U . . . C28A C 1.141(2) 0.4413(11) 0.1758(10) 0.118(5) Uani 1 1 d . . . . . H28C H 1.236701 0.387268 0.219450 0.142 Uiso 1 1 calc R U . . . C29 C 1.3481(11) 0.7941(7) 0.1715(5) 0.0469(18) Uani 1 1 d . . . . . C30 C 1.5290(13) 0.8839(9) 0.1934(7) 0.068(2) Uani 1 1 d . . . . . H30A H 1.655978 0.854286 0.226951 0.081 Uiso 1 1 calc R U . . . C31 C 1.517(2) 1.0185(13) 0.1642(11) 0.105(4) Uani 1 1 d . . . . . H31A H 1.636754 1.080139 0.178141 0.126 Uiso 1 1 calc R U . . . C32 C 1.333(3) 1.0616(12) 0.1160(10) 0.110(5) Uani 1 1 d . . . . . H32A H 1.327379 1.151840 0.095361 0.132 Uiso 1 1 calc R U . . . C33 C 1.158(2) 0.9740(13) 0.0977(7) 0.088(3) Uani 1 1 d . . . . . H33A H 1.030648 1.004481 0.065147 0.106 Uiso 1 1 calc R U . . . C34 C 1.1647(12) 0.8422(8) 0.1259(6) 0.056(2) Uani 1 1 d . . . . . H34A H 1.040548 0.783577 0.113633 0.067 Uiso 1 1 calc R U . . . C35 C 0.6701(13) 0.7725(8) 0.4871(7) 0.069(2) Uani 1 1 d . . . . . H35A H 0.541035 0.774350 0.440926 0.103 Uiso 1 1 calc R U . . . H35B H 0.785934 0.827500 0.461039 0.103 Uiso 1 1 calc R U . . . H35C H 0.634331 0.812830 0.562178 0.103 Uiso 1 1 calc R U . . . C36 C 0.9618(14) 0.6159(9) 0.5880(6) 0.070(2) Uani 1 1 d . . . . . H36A H 1.027229 0.524892 0.593887 0.104 Uiso 1 1 calc R U . . . H36B H 0.893677 0.654987 0.657141 0.104 Uiso 1 1 calc R U . . . H36C H 1.074571 0.679977 0.570946 0.104 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0720(12) 0.0639(13) 0.0456(13) 0.0226(10) 0.0267(10) 0.0261(10) O1 0.099(4) 0.140(6) 0.055(4) 0.054(4) 0.041(3) 0.057(4) O2 0.055(3) 0.053(3) 0.042(3) 0.018(3) 0.011(2) 0.013(2) O3 0.105(4) 0.090(5) 0.066(4) 0.028(3) 0.032(3) 0.058(4) C2 0.086(6) 0.081(7) 0.070(6) 0.037(5) 0.040(5) 0.030(5) C3 0.043(3) 0.049(5) 0.044(4) 0.006(3) 0.011(3) 0.003(3) N4 0.063(4) 0.069(4) 0.036(3) 0.025(3) 0.019(3) 0.031(3) C5 0.049(4) 0.041(4) 0.037(4) 0.015(3) 0.010(3) 0.004(3) C6 0.054(4) 0.047(4) 0.032(4) 0.011(3) 0.012(3) 0.013(3) C7 0.075(5) 0.051(5) 0.051(5) 0.017(4) 0.014(4) 0.010(4) C8 0.127(8) 0.086(7) 0.055(5) 0.038(5) 0.042(5) 0.052(6) C8AA 0.076(14) 0.095(19) 0.045(11) 0.021(12) 0.021(10) 0.035(13) C8AB 0.053(11) 0.030(11) 0.027(10) 0.017(8) 0.008(8) 0.009(8) C9 0.041(4) 0.045(4) 0.032(4) 0.007(3) 0.012(3) 0.005(3) C10 0.061(5) 0.050(5) 0.055(5) 0.012(4) -0.002(4) 0.007(4) C11 0.084(6) 0.067(7) 0.068(6) 0.014(5) 0.016(5) 0.016(6) C12 0.142(10) 0.058(7) 0.072(7) 0.015(6) 0.052(7) 0.002(7) C13 0.098(7) 0.089(8) 0.035(5) -0.003(5) 0.000(5) -0.035(6) C14 0.055(4) 0.081(6) 0.043(5) 0.019(4) 0.006(4) -0.003(4) C15 0.119(8) 0.061(6) 0.042(5) 0.011(4) 0.008(5) 0.010(5) C16 0.069(5) 0.084(6) 0.061(5) 0.032(5) 0.011(4) -0.015(4) S21 0.0635(11) 0.0588(13) 0.0472(13) -0.0018(10) 0.0253(10) -0.0138(10) O21 0.101(4) 0.060(4) 0.045(3) -0.011(3) 0.033(3) -0.009(3) O22 0.056(3) 0.049(3) 0.040(3) -0.002(2) 0.011(2) -0.006(2) O23 0.095(4) 0.091(5) 0.062(4) -0.010(3) 0.027(3) -0.043(4) C22 0.094(6) 0.068(6) 0.083(7) -0.011(5) 0.059(6) -0.010(5) C23 0.053(4) 0.040(4) 0.054(5) 0.008(3) 0.018(3) 0.010(3) N24 0.062(4) 0.036(4) 0.053(4) -0.004(3) 0.025(3) -0.015(3) C25 0.045(4) 0.037(4) 0.035(4) -0.002(3) 0.010(3) 0.005(3) C26 0.055(4) 0.033(4) 0.034(4) -0.002(3) 0.015(3) -0.004(3) C27 0.067(5) 0.043(5) 0.052(5) 0.004(4) 0.010(4) -0.009(4) C28 0.101(6) 0.069(6) 0.062(6) -0.023(5) 0.034(5) -0.032(5) C28A 0.156(11) 0.067(7) 0.113(9) -0.043(6) 0.089(8) -0.046(7) C29 0.060(4) 0.042(4) 0.037(4) -0.001(3) 0.019(3) -0.004(4) C30 0.071(5) 0.057(6) 0.073(6) 0.004(4) 0.016(4) -0.014(4) C31 0.128(10) 0.067(9) 0.119(11) 0.005(7) 0.068(8) -0.035(7) C32 0.197(15) 0.054(7) 0.089(9) 0.032(6) 0.089(10) 0.036(9) C33 0.131(9) 0.096(9) 0.042(5) 0.024(5) 0.027(6) 0.060(7) C34 0.065(5) 0.059(6) 0.042(4) 0.005(4) 0.001(4) 0.013(4) C35 0.071(5) 0.068(6) 0.060(5) -0.011(4) 0.010(4) 0.019(4) C36 0.094(6) 0.083(7) 0.029(5) 0.001(4) 0.005(4) -0.011(5) _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C6 1.736(7) . ? S1 C15 1.791(9) . ? S1 C16 1.810(8) . ? O1 C2 1.324(9) . ? O1 C8AA 1.44(2) . ? O1 C8AB 1.452(19) . ? O2 C5 1.224(7) . ? O3 C7 1.239(8) . ? C2 C3 1.545(10) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 N4 1.454(8) . ? C3 C9 1.505(9) . ? C3 H3A 0.9900 . ? N4 C5 1.374(8) . ? N4 C8AA 1.444(17) . ? N4 C8AB 1.571(17) . ? C5 C6 1.436(9) . ? C6 C7 1.425(10) . ? C7 C8 1.522(10) . ? C8 C8AB 1.37(2) . ? C8 C8AA 1.41(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C8 H8D 0.9800 . ? C8AA H8AA 0.9900 . ? C8AB H8AB 0.9900 . ? C9 C14 1.379(10) . ? C9 C10 1.396(10) . ? C10 C11 1.348(12) . ? C10 H10A 0.9400 . ? C11 C12 1.360(14) . ? C11 H11A 0.9400 . ? C12 C13 1.352(14) . ? C12 H12A 0.9400 . ? C13 C14 1.400(12) . ? C13 H13A 0.9400 . ? C14 H14A 0.9400 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15C 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 H16C 0.9700 . ? S21 C26 1.739(7) . ? S21 C36 1.777(8) . ? S21 C35 1.789(8) . ? O21 C28A 1.362(10) . ? O21 C22 1.388(9) . ? O22 C25 1.234(8) . ? O23 C27 1.223(8) . ? C22 C23 1.546(10) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 N24 1.466(9) . ? C23 C29 1.503(10) . ? C23 H23A 0.9900 . ? N24 C25 1.369(8) . ? N24 C28A 1.461(10) . ? C25 C26 1.427(9) . ? C26 C27 1.419(10) . ? C27 C28 1.520(10) . ? C28 C28A 1.337(12) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28A H28C 0.9900 . ? C29 C34 1.361(10) . ? C29 C30 1.398(10) . ? C30 C31 1.395(14) . ? C30 H30A 0.9400 . ? C31 C32 1.358(18) . ? C31 H31A 0.9400 . ? C32 C33 1.353(17) . ? C32 H32A 0.9400 . ? C33 C34 1.363(12) . ? C33 H33A 0.9400 . ? C34 H34A 0.9400 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C35 H35C 0.9700 . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C36 H36C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 S1 C15 107.6(4) . . ? C6 S1 C16 107.2(4) . . ? C15 S1 C16 100.4(4) . . ? C2 O1 C8AA 109.6(9) . . ? C2 O1 C8AB 107.9(8) . . ? O1 C2 C3 110.9(6) . . ? O1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? O1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.0 . . ? N4 C3 C9 114.6(6) . . ? N4 C3 C2 98.5(6) . . ? C9 C3 C2 112.7(6) . . ? N4 C3 H3A 110.1 . . ? C9 C3 H3A 110.1 . . ? C2 C3 H3A 110.1 . . ? C5 N4 C8AA 124.5(7) . . ? C5 N4 C3 123.4(6) . . ? C8AA N4 C3 112.1(7) . . ? C5 N4 C8AB 115.3(8) . . ? C3 N4 C8AB 105.6(7) . . ? O2 C5 N4 120.6(6) . . ? O2 C5 C6 124.5(6) . . ? N4 C5 C6 114.9(6) . . ? C7 C6 C5 124.1(6) . . ? C7 C6 S1 115.2(5) . . ? C5 C6 S1 120.7(5) . . ? O3 C7 C6 125.2(7) . . ? O3 C7 C8 120.2(7) . . ? C6 C7 C8 114.6(6) . . ? C8AB C8 C7 116.6(9) . . ? C8AA C8 C7 116.5(9) . . ? C8AA C8 H8A 108.2 . . ? C7 C8 H8A 108.2 . . ? C8AA C8 H8B 108.2 . . ? C7 C8 H8B 108.2 . . ? H8A C8 H8B 107.3 . . ? C8AB C8 H8C 108.1 . . ? C7 C8 H8C 108.1 . . ? C8AB C8 H8D 108.1 . . ? C7 C8 H8D 108.1 . . ? H8C C8 H8D 107.3 . . ? C8 C8AA O1 111(2) . . ? C8 C8AA N4 113.1(17) . . ? O1 C8AA N4 102.1(14) . . ? C8 C8AA H8AA 110.0 . . ? O1 C8AA H8AA 110.0 . . ? N4 C8AA H8AA 110.0 . . ? C8 C8AB O1 112.7(17) . . ? C8 C8AB N4 107.7(15) . . ? O1 C8AB N4 95.7(12) . . ? C8 C8AB H8AB 113.1 . . ? O1 C8AB H8AB 113.1 . . ? N4 C8AB H8AB 113.1 . . ? C14 C9 C10 117.9(7) . . ? C14 C9 C3 123.1(7) . . ? C10 C9 C3 118.9(6) . . ? C11 C10 C9 122.1(8) . . ? C11 C10 H10A 119.0 . . ? C9 C10 H10A 119.0 . . ? C10 C11 C12 119.5(9) . . ? C10 C11 H11A 120.3 . . ? C12 C11 H11A 120.3 . . ? C13 C12 C11 120.8(10) . . ? C13 C12 H12A 119.6 . . ? C11 C12 H12A 119.6 . . ? C12 C13 C14 120.5(9) . . ? C12 C13 H13A 119.8 . . ? C14 C13 H13A 119.8 . . ? C9 C14 C13 119.2(8) . . ? C9 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? S1 C15 H15A 109.5 . . ? S1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? S1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S1 C16 H16A 109.5 . . ? S1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? S1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C26 S21 C36 106.6(4) . . ? C26 S21 C35 107.0(4) . . ? C36 S21 C35 100.6(4) . . ? C28A O21 C22 111.5(6) . . ? O21 C22 C23 108.2(6) . . ? O21 C22 H22A 110.1 . . ? C23 C22 H22A 110.1 . . ? O21 C22 H22B 110.1 . . ? C23 C22 H22B 110.1 . . ? H22A C22 H22B 108.4 . . ? N24 C23 C29 113.7(5) . . ? N24 C23 C22 100.2(6) . . ? C29 C23 C22 111.3(6) . . ? N24 C23 H23A 110.4 . . ? C29 C23 H23A 110.4 . . ? C22 C23 H23A 110.4 . . ? C25 N24 C28A 120.4(6) . . ? C25 N24 C23 124.7(6) . . ? C28A N24 C23 109.1(6) . . ? O22 C25 N24 119.5(6) . . ? O22 C25 C26 125.3(6) . . ? N24 C25 C26 115.1(6) . . ? C27 C26 C25 124.7(6) . . ? C27 C26 S21 114.9(5) . . ? C25 C26 S21 120.3(5) . . ? O23 C27 C26 126.3(7) . . ? O23 C27 C28 119.2(7) . . ? C26 C27 C28 114.5(6) . . ? C28A C28 C27 118.1(7) . . ? C28A C28 H28A 107.8 . . ? C27 C28 H28A 107.8 . . ? C28A C28 H28B 107.8 . . ? C27 C28 H28B 107.8 . . ? H28A C28 H28B 107.1 . . ? C28 C28A O21 123.8(10) . . ? C28 C28A N24 117.1(8) . . ? O21 C28A N24 105.6(7) . . ? C28 C28A H28C 102.3 . . ? O21 C28A H28C 102.3 . . ? N24 C28A H28C 102.3 . . ? C34 C29 C30 119.1(7) . . ? C34 C29 C23 122.8(7) . . ? C30 C29 C23 117.9(7) . . ? C31 C30 C29 118.4(10) . . ? C31 C30 H30A 120.8 . . ? C29 C30 H30A 120.8 . . ? C32 C31 C30 120.9(11) . . ? C32 C31 H31A 119.6 . . ? C30 C31 H31A 119.6 . . ? C33 C32 C31 119.7(10) . . ? C33 C32 H32A 120.2 . . ? C31 C32 H32A 120.2 . . ? C32 C33 C34 120.9(10) . . ? C32 C33 H33A 119.6 . . ? C34 C33 H33A 119.6 . . ? C29 C34 C33 121.0(9) . . ? C29 C34 H34A 119.5 . . ? C33 C34 H34A 119.5 . . ? S21 C35 H35A 109.5 . . ? S21 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? S21 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? S21 C36 H36A 109.5 . . ? S21 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? S21 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8AA O1 C2 C3 19.1(18) . . . . ? C8AB O1 C2 C3 -26.6(15) . . . . ? O1 C2 C3 N4 -3.6(10) . . . . ? O1 C2 C3 C9 -125.0(8) . . . . ? C9 C3 N4 C5 -74.7(9) . . . . ? C2 C3 N4 C5 165.4(7) . . . . ? C9 C3 N4 C8AA 106.6(18) . . . . ? C2 C3 N4 C8AA -13.3(18) . . . . ? C9 C3 N4 C8AB 149.6(11) . . . . ? C2 C3 N4 C8AB 29.7(12) . . . . ? C8AA N4 C5 O2 -167.1(19) . . . . ? C3 N4 C5 O2 14.4(11) . . . . ? C8AB N4 C5 O2 146.3(12) . . . . ? C8AA N4 C5 C6 12(2) . . . . ? C3 N4 C5 C6 -166.9(7) . . . . ? C8AB N4 C5 C6 -35.0(13) . . . . ? O2 C5 C6 C7 -177.6(7) . . . . ? N4 C5 C6 C7 3.7(11) . . . . ? O2 C5 C6 S1 3.1(10) . . . . ? N4 C5 C6 S1 -175.5(6) . . . . ? C15 S1 C6 C7 128.8(6) . . . . ? C16 S1 C6 C7 -124.0(6) . . . . ? C15 S1 C6 C5 -51.9(7) . . . . ? C16 S1 C6 C5 55.3(7) . . . . ? C5 C6 C7 O3 -175.4(8) . . . . ? S1 C6 C7 O3 3.9(11) . . . . ? C5 C6 C7 C8 4.3(12) . . . . ? S1 C6 C7 C8 -176.4(7) . . . . ? O3 C7 C8 C8AB -157.3(15) . . . . ? C6 C7 C8 C8AB 23.0(18) . . . . ? O3 C7 C8 C8AA 152.0(18) . . . . ? C6 C7 C8 C8AA -28(2) . . . . ? C7 C8 C8AA O1 155.3(12) . . . . ? C7 C8 C8AA N4 41(3) . . . . ? C2 O1 C8AA C8 -147.1(15) . . . . ? C2 O1 C8AA N4 -26(2) . . . . ? C5 N4 C8AA C8 -35(3) . . . . ? C3 N4 C8AA C8 144.1(16) . . . . ? C5 N4 C8AA O1 -154.4(10) . . . . ? C3 N4 C8AA O1 24(2) . . . . ? C7 C8 C8AB O1 -155.2(10) . . . . ? C7 C8 C8AB N4 -51(2) . . . . ? C2 O1 C8AB C8 153.9(13) . . . . ? C2 O1 C8AB N4 42.0(15) . . . . ? C5 N4 C8AB C8 59.7(19) . . . . ? C3 N4 C8AB C8 -160.5(12) . . . . ? C5 N4 C8AB O1 175.8(9) . . . . ? C3 N4 C8AB O1 -44.4(15) . . . . ? N4 C3 C9 C14 -40.7(9) . . . . ? C2 C3 C9 C14 71.0(8) . . . . ? N4 C3 C9 C10 143.0(6) . . . . ? C2 C3 C9 C10 -105.4(7) . . . . ? C14 C9 C10 C11 0.2(11) . . . . ? C3 C9 C10 C11 176.8(7) . . . . ? C9 C10 C11 C12 -0.5(13) . . . . ? C10 C11 C12 C13 0.6(14) . . . . ? C11 C12 C13 C14 -0.5(14) . . . . ? C10 C9 C14 C13 -0.1(10) . . . . ? C3 C9 C14 C13 -176.5(6) . . . . ? C12 C13 C14 C9 0.2(12) . . . . ? C28A O21 C22 C23 -8.0(12) . . . . ? O21 C22 C23 N24 -6.9(9) . . . . ? O21 C22 C23 C29 -127.6(8) . . . . ? C29 C23 N24 C25 -69.4(9) . . . . ? C22 C23 N24 C25 171.8(7) . . . . ? C29 C23 N24 C28A 137.3(9) . . . . ? C22 C23 N24 C28A 18.5(10) . . . . ? C28A N24 C25 O22 161.3(9) . . . . ? C23 N24 C25 O22 10.8(10) . . . . ? C28A N24 C25 C26 -21.5(11) . . . . ? C23 N24 C25 C26 -172.0(6) . . . . ? O22 C25 C26 C27 178.1(7) . . . . ? N24 C25 C26 C27 1.1(10) . . . . ? O22 C25 C26 S21 -0.1(10) . . . . ? N24 C25 C26 S21 -177.1(5) . . . . ? C36 S21 C26 C27 129.7(6) . . . . ? C35 S21 C26 C27 -123.4(6) . . . . ? C36 S21 C26 C25 -51.9(7) . . . . ? C35 S21 C26 C25 55.0(7) . . . . ? C25 C26 C27 O23 -174.1(8) . . . . ? S21 C26 C27 O23 4.1(11) . . . . ? C25 C26 C27 C28 3.7(11) . . . . ? S21 C26 C27 C28 -178.1(6) . . . . ? O23 C27 C28 C28A -169.1(11) . . . . ? C26 C27 C28 C28A 12.9(14) . . . . ? C27 C28 C28A O21 -167.4(9) . . . . ? C27 C28 C28A N24 -32.6(17) . . . . ? C22 O21 C28A C28 158.7(12) . . . . ? C22 O21 C28A N24 19.6(13) . . . . ? C25 N24 C28A C28 38.8(16) . . . . ? C23 N24 C28A C28 -166.6(11) . . . . ? C25 N24 C28A O21 -179.0(8) . . . . ? C23 N24 C28A O21 -24.4(12) . . . . ? N24 C23 C29 C34 -38.8(9) . . . . ? C22 C23 C29 C34 73.5(8) . . . . ? N24 C23 C29 C30 145.4(7) . . . . ? C22 C23 C29 C30 -102.3(8) . . . . ? C34 C29 C30 C31 -2.0(11) . . . . ? C23 C29 C30 C31 173.9(7) . . . . ? C29 C30 C31 C32 0.2(15) . . . . ? C30 C31 C32 C33 1.2(17) . . . . ? C31 C32 C33 C34 -0.8(16) . . . . ? C30 C29 C34 C33 2.5(11) . . . . ? C23 C29 C34 C33 -173.2(7) . . . . ? C32 C33 C34 C29 -1.1(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C8AB^b H8AB^b O3 0.99 2.61 3.47(3) 145.0 1_455 yes C15 H15A O22 0.97 2.46 3.248(10) 138.6 1_445 yes C15 H15C O2 0.97 2.42 3.094(9) 126.5 . yes C16 H16C O23 0.97 2.19 3.103(9) 156.2 . yes C35 H35A O22 0.97 2.47 3.378(10) 155.3 1_455 yes C35 H35B O22 0.97 2.48 3.157(9) 126.5 . yes C35 H35C O3 0.97 2.28 3.131(9) 146.1 1_565 yes C36 H36A O2 0.97 2.53 3.278(10) 134.3 1_655 yes C36 H36C O22 0.97 2.42 3.091(9) 125.9 . yes _refine_diff_density_max 0.332 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.045 _shelx_res_file ; TITL enr101_a.res in P1 enr101.res created by SHELXL-2018/1 at 08:48:28 on 18-Apr-2018 CELL 0.56083 6.0976 9.5728 12.3463 99.389 90.433 89.796 ZERR 2 0.0004 0.0008 0.0010 0.007 0.006 0.007 LATT -1 SFAC C H N O S UNIT 30 34 2 6 2 SIZE 0.4 0.15 0.05 TEMP -30 L.S. 20 PLAN 20 OMIT 1 0 3 OMIT -1 0 -3 OMIT -1 0 1 OMIT -2 0 -2 BOND $H CONF EQIV $1 x-1, y, z EQIV $2 x-1, y-1, z EQIV $3 x, y+1, z EQIV $4 x+1, y, z HTAB C8AB O3_$1 HTAB C15 O22_$2 HTAB C15 O2 HTAB C16 O23 HTAB C35 O22_$1 HTAB C35 O22 HTAB C35 O3_$3 HTAB C36 O2_$4 HTAB C36 O22 FMAP 2 ACTA WGHT 0.051100 FVAR 1.46001 0.54635 S1 5 0.272815 0.099416 0.499903 11.00000 0.07198 0.06390 = 0.04556 0.02263 0.02667 0.02605 O1 4 -0.204139 0.115539 0.906668 11.00000 0.09894 0.13976 = 0.05542 0.05382 0.04100 0.05700 O2 4 -0.121795 0.278143 0.589557 11.00000 0.05486 0.05343 = 0.04248 0.01810 0.01144 0.01251 O3 4 0.385383 -0.061138 0.675705 11.00000 0.10458 0.09035 = 0.06593 0.02820 0.03161 0.05834 C2 1 -0.364677 0.205683 0.895473 11.00000 0.08576 0.08106 = 0.07049 0.03690 0.04023 0.03013 AFIX 23 H2A 2 -0.365769 0.281447 0.959287 11.00000 -1.20000 H2B 2 -0.505724 0.156396 0.892495 11.00000 -1.20000 AFIX 0 C3 1 -0.335714 0.270573 0.789847 11.00000 0.04261 0.04892 = 0.04384 0.00558 0.01106 0.00297 AFIX 13 H3A 2 -0.452370 0.236147 0.735966 11.00000 -1.20000 AFIX 0 N4 3 -0.127027 0.205258 0.754466 11.00000 0.06330 0.06892 = 0.03646 0.02475 0.01851 0.03098 C5 1 -0.044322 0.202073 0.650894 11.00000 0.04944 0.04090 = 0.03654 0.01485 0.01015 0.00384 C6 1 0.137195 0.107113 0.623897 11.00000 0.05397 0.04685 = 0.03172 0.01071 0.01159 0.01309 C7 1 0.221078 0.015214 0.694284 11.00000 0.07483 0.05139 = 0.05125 0.01694 0.01416 0.00996 C8 1 0.091898 0.016402 0.799407 11.00000 0.12667 0.08633 = 0.05545 0.03758 0.04247 0.05221 PART 1 21 AFIX 23 H8A 2 -0.014677 -0.061038 0.786715 21.00000 -1.20000 H8B 2 0.193701 -0.003968 0.856655 21.00000 -1.20000 AFIX 23 PART 0 PART 2 -21 H8C 2 0.094497 -0.079553 0.817469 -21.00000 -1.20000 H8D 2 0.168253 0.078167 0.858863 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C8AA 1 -0.021373 0.142085 0.839776 21.00000 0.07573 0.09503 = 0.04537 0.02111 0.02086 0.03476 AFIX 13 H8AA 2 0.079782 0.210981 0.882692 21.00000 -1.20000 AFIX 0 PART 2 C8AB 1 -0.122546 0.059906 0.797959 -21.00000 0.05333 0.03048 = 0.02667 0.01712 0.00782 0.00923 AFIX 13 H8AB 2 -0.220452 -0.011976 0.756010 -21.00000 -1.20000 AFIX 0 PART 0 C9 1 -0.333452 0.429910 0.811536 11.00000 0.04108 0.04469 = 0.03152 0.00692 0.01248 0.00466 C10 1 -0.517987 0.503299 0.783292 11.00000 0.06113 0.05030 = 0.05522 0.01177 -0.00234 0.00662 AFIX 43 H10A 2 -0.636568 0.451789 0.747987 11.00000 -1.20000 AFIX 0 C11 1 -0.531434 0.645746 0.805071 11.00000 0.08399 0.06682 = 0.06800 0.01448 0.01604 0.01637 AFIX 43 H11A 2 -0.657280 0.692437 0.784649 11.00000 -1.20000 AFIX 0 C12 1 -0.361566 0.721321 0.856799 11.00000 0.14164 0.05818 = 0.07245 0.01469 0.05153 0.00225 AFIX 43 H12A 2 -0.371240 0.820574 0.872623 11.00000 -1.20000 AFIX 0 C13 1 -0.178901 0.655481 0.885758 11.00000 0.09762 0.08870 = 0.03502 -0.00324 0.00024 -0.03490 AFIX 43 H13A 2 -0.062482 0.709312 0.921004 11.00000 -1.20000 AFIX 0 C14 1 -0.161933 0.507671 0.863616 11.00000 0.05468 0.08078 = 0.04310 0.01945 0.00614 -0.00273 AFIX 43 H14A 2 -0.035073 0.461999 0.884025 11.00000 -1.20000 AFIX 0 C15 1 0.070347 0.074104 0.392744 11.00000 0.11927 0.06064 = 0.04164 0.01086 0.00764 0.01016 AFIX 137 H15A 2 0.013375 -0.021532 0.384799 11.00000 -1.50000 H15B 2 0.136398 0.088851 0.324290 11.00000 -1.50000 H15C 2 -0.048416 0.141280 0.411091 11.00000 -1.50000 AFIX 0 C16 1 0.362488 0.277221 0.491092 11.00000 0.06944 0.08381 = 0.06140 0.03209 0.01149 -0.01522 AFIX 137 H16A 2 0.432323 0.318487 0.559672 11.00000 -1.50000 H16B 2 0.236884 0.334414 0.477284 11.00000 -1.50000 H16C 2 0.466318 0.274052 0.431598 11.00000 -1.50000 AFIX 0 S21 5 0.760249 0.593597 0.481961 11.00000 0.06350 0.05880 = 0.04721 -0.00181 0.02527 -0.01377 O21 4 1.253292 0.432453 0.079924 11.00000 0.10135 0.05967 = 0.04526 -0.01111 0.03284 -0.00859 O22 4 1.149332 0.738050 0.391296 11.00000 0.05649 0.04923 = 0.04024 -0.00197 0.01066 -0.00630 O23 4 0.654337 0.357658 0.306023 11.00000 0.09472 0.09138 = 0.06225 -0.01029 0.02744 -0.04316 C22 1 1.406693 0.540158 0.084754 11.00000 0.09360 0.06809 = 0.08339 -0.01052 0.05893 -0.00990 AFIX 23 H22A 2 1.388079 0.589418 0.021649 11.00000 -1.20000 H22B 2 1.555400 0.500718 0.082985 11.00000 -1.20000 AFIX 0 C23 1 1.371732 0.644546 0.192735 11.00000 0.05270 0.03965 = 0.05417 0.00833 0.01812 0.00968 AFIX 13 H23A 2 1.494294 0.637465 0.244625 11.00000 -1.20000 AFIX 0 N24 3 1.170228 0.586692 0.231834 11.00000 0.06210 0.03619 = 0.05282 -0.00413 0.02530 -0.01484 C25 1 1.079520 0.630188 0.332853 11.00000 0.04465 0.03695 = 0.03479 -0.00228 0.00977 0.00510 C26 1 0.900115 0.546624 0.359083 11.00000 0.05530 0.03255 = 0.03448 -0.00156 0.01498 -0.00356 C27 1 0.817424 0.425097 0.289682 11.00000 0.06666 0.04267 = 0.05205 0.00389 0.01003 -0.00895 C28 1 0.945219 0.382052 0.184170 11.00000 0.10091 0.06891 = 0.06192 -0.02307 0.03405 -0.03163 AFIX 23 H28A 2 0.966079 0.279183 0.173667 11.00000 -1.20000 H28B 2 0.853460 0.402717 0.123193 11.00000 -1.20000 AFIX 0 C28A 1 1.141274 0.441258 0.175801 11.00000 0.15571 0.06731 = 0.11309 -0.04346 0.08935 -0.04629 AFIX 13 H28C 2 1.236701 0.387268 0.219450 11.00000 -1.20000 AFIX 0 C29 1 1.348147 0.794096 0.171523 11.00000 0.05961 0.04180 = 0.03701 -0.00148 0.01930 -0.00429 C30 1 1.528988 0.883899 0.193386 11.00000 0.07102 0.05741 = 0.07270 0.00395 0.01586 -0.01397 AFIX 43 H30A 2 1.655978 0.854286 0.226951 11.00000 -1.20000 AFIX 0 C31 1 1.516526 1.018466 0.164220 11.00000 0.12773 0.06724 = 0.11899 0.00514 0.06829 -0.03462 AFIX 43 H31A 2 1.636754 1.080139 0.178141 11.00000 -1.20000 AFIX 0 C32 1 1.332960 1.061592 0.115964 11.00000 0.19674 0.05375 = 0.08858 0.03197 0.08941 0.03637 AFIX 43 H32A 2 1.327379 1.151840 0.095361 11.00000 -1.20000 AFIX 0 C33 1 1.158214 0.974014 0.097705 11.00000 0.13137 0.09563 = 0.04156 0.02422 0.02704 0.06021 AFIX 43 H33A 2 1.030648 1.004481 0.065147 11.00000 -1.20000 AFIX 0 C34 1 1.164654 0.842153 0.125893 11.00000 0.06467 0.05899 = 0.04191 0.00475 0.00092 0.01283 AFIX 43 H34A 2 1.040548 0.783577 0.113633 11.00000 -1.20000 AFIX 0 C35 1 0.670069 0.772545 0.487116 11.00000 0.07119 0.06807 = 0.05958 -0.01070 0.01050 0.01920 AFIX 137 H35A 2 0.541035 0.774350 0.440926 11.00000 -1.50000 H35B 2 0.785934 0.827500 0.461039 11.00000 -1.50000 H35C 2 0.634331 0.812830 0.562178 11.00000 -1.50000 AFIX 0 C36 1 0.961814 0.615894 0.588025 11.00000 0.09433 0.08289 = 0.02899 0.00110 0.00496 -0.01082 AFIX 137 H36A 2 1.027229 0.524892 0.593887 11.00000 -1.50000 H36B 2 0.893677 0.654987 0.657141 11.00000 -1.50000 H36C 2 1.074571 0.679977 0.570946 11.00000 -1.50000 AFIX 0 HKLF 4 REM enr101_a.res in P1 REM R1 = 0.0532 for 2713 Fo > 4sig(Fo) and 0.1036 for all 4804 data REM 375 parameters refined using 3 restraints END WGHT 0.0510 0.0000 REM Highest difference peak 0.332, deepest hole -0.202, 1-sigma level 0.045 Q1 1 -0.1144 0.2159 0.9378 11.00000 0.05 0.33 Q2 1 -0.2722 0.1721 0.4885 11.00000 0.05 0.27 Q3 1 0.3107 0.5222 0.4969 11.00000 0.05 0.21 Q4 1 0.7906 1.0161 0.4842 11.00000 0.05 0.21 Q5 1 -0.5277 0.0592 0.8275 11.00000 0.05 0.20 Q6 1 0.8850 0.2955 0.1381 11.00000 0.05 0.19 Q7 1 1.3725 1.2204 0.1753 11.00000 0.05 0.19 Q8 1 1.2625 0.6826 0.5053 11.00000 0.05 0.19 Q9 1 0.0512 0.0096 0.5929 11.00000 0.05 0.17 Q10 1 -0.1523 0.9343 0.9225 11.00000 0.05 0.17 Q11 1 1.2001 0.4327 0.1888 11.00000 0.05 0.16 Q12 1 -0.0415 0.0706 0.5862 11.00000 0.05 0.16 Q13 1 -0.3577 0.8749 0.8377 11.00000 0.05 0.16 Q14 1 1.1254 0.6688 0.0626 11.00000 0.05 0.16 Q15 1 1.2368 0.3239 0.2385 11.00000 0.05 0.16 Q16 1 0.7911 0.4971 0.0825 11.00000 0.05 0.16 Q17 1 -0.3247 0.6995 0.7368 11.00000 0.05 0.15 Q18 1 -0.8013 0.5038 0.7761 11.00000 0.05 0.15 Q19 1 0.8149 0.8521 0.5578 11.00000 0.05 0.15 Q20 1 -0.2318 0.8213 0.8783 11.00000 0.05 0.15 ; _shelx_res_checksum 83697 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_23a _database_code_depnum_ccdc_archive 'CCDC 2125366' loop_ _audit_author_name _audit_author_address 'Sylvain Bernes' ;Instituto de Fisica, BUAP, Puebla Mexico ; _audit_update_record ; 2021-11-30 deposited with the CCDC. 2022-01-21 downloaded from the CCDC. ; # Clave Lab. : ENR33_1 # Clave IF-UAP: ENR33_1 # Clave datos : ... \BUAP\Sylvain\ENR33_1\50mm_1\ _database_code_CAS ? _database_code_CSD ? _audit_creation_method SHELXL-2018/1 _shelx_SHELXL_version_number 2018/1 _audit_creation_date 2018-02-13 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 N O3 S' _chemical_formula_sum 'C16 H19 N O3 S' _chemical_formula_weight 305.38 _chemical_absolute_configuration ad _chemical_optical_rotation ? _chemical_properties_physical ? _chemical_properties_biological ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.0826 0.0763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _shelx_space_group_comment ? loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.46490(10) _cell_length_b 10.7205(4) _cell_length_c 26.0834(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1528.13(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 27016 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 29.15 _exptl_crystal_recrystallization_method ; Re-crystallisation from solvent: CH2Cl2/benzine ; _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_F_000 648 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.300 _exptl_absorpt_coefficient_mu 0.121 _shelx_estimated_absorpt_T_min 0.953 _shelx_estimated_absorpt_T_max 0.964 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5466 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _diffrn_ambient_temperature 295(1) _diffrn_ambient_environment air _diffrn_measurement_specimen_support 'Mitegen 50um' _diffrn_source 'Sealed X-ray tube' _diffrn_source_type 'Axo Astix-f Microfocus source' _diffrn_source_voltage 65 _diffrn_source_current 0.600 _diffrn_source_power 0.039 _diffrn_radiation_collimation '0.3 mm diameter' _diffrn_radiation_probe x-ray _diffrn_radiation_type AgK\a _diffrn_radiation_wavelength 0.56083 _diffrn_radiation_monochromator 'Graded multilayer mirror' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Stoe Stadivari' _diffrn_detector 'Reverse-biased silicon diode array' _diffrn_detector_type 'Dectris Pilatus 100K R' _diffrn_measurement_method '\w scans' _diffrn_measurement_details ; 1619 frames, 35-45 s/frame, 1 deg./frame, detector distance = 50 mm ; _diffrn_detector_area_resol_mean 5.81 _diffrn_reflns_number 34956 _diffrn_reflns_av_unetI/netI 0.0203 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.885 _diffrn_reflns_theta_max 20.998 _diffrn_reflns_theta_full 19.664 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_point_group_measured_fraction_full 0.998 _reflns_number_total 3324 _reflns_number_gt 3073 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.703 _reflns_Friedel_fraction_max 1.000 _reflns_Friedel_fraction_full 1.000 _reflns_special_details ? _computing_data_collection 'X-AREA (Stoe & Cie, 2015)' _computing_cell_refinement X-AREA _computing_data_reduction X-AREA _computing_structure_solution 'SHELXT-2014/5 (Sheldrick, 2015a)' _computing_structure_refinement 'SHELXL-2018/1 (Sheldrick, 2018)' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)' _computing_publication_material 'PublCif (Westrip, 2010)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0598P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method 'SHELXL-2018/1 (Sheldrick 2018)' _refine_ls_extinction_coef 0.039(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Flack x determined using 1208 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.05(4) _refine_ls_number_reflns 3324 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0870 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.37953(10) 0.36461(5) 0.27142(2) 0.04486(16) Uani 1 1 d . . . . . O1 O 0.5974(3) 0.54107(16) 0.47647(6) 0.0507(4) Uani 1 1 d . . . . . O2 O 0.2044(3) 0.58577(15) 0.32652(6) 0.0462(4) Uani 1 1 d . . . . . O3 O 0.7885(3) 0.26374(17) 0.33920(7) 0.0585(4) Uani 1 1 d . . . . . C2 C 0.4079(4) 0.6324(2) 0.48173(8) 0.0494(5) Uani 1 1 d . . . . . H2A H 0.468312 0.706395 0.498983 0.059 Uiso 1 1 calc R U . . . H2B H 0.270629 0.599097 0.500945 0.059 Uiso 1 1 calc R U . . . C3 C 0.3334(4) 0.6621(2) 0.42647(7) 0.0392(4) Uani 1 1 d . . . . . H3A H 0.158693 0.682430 0.424905 0.047 Uiso 1 1 calc R U . . . N4 N 0.3782(3) 0.54116(15) 0.40287(6) 0.0370(4) Uani 1 1 d . . . . . C5 C 0.3380(3) 0.51678(19) 0.35212(7) 0.0356(4) Uani 1 1 d . . . . . C6 C 0.4663(4) 0.4084(2) 0.33239(8) 0.0407(4) Uani 1 1 d . . . . . C7 C 0.6653(4) 0.3501(2) 0.35736(8) 0.0425(5) Uani 1 1 d . . . . . C8 C 0.7334(4) 0.4030(2) 0.40951(9) 0.0465(5) Uani 1 1 d . . . . . H8A H 0.803469 0.337125 0.430368 0.056 Uiso 1 1 calc R U . . . H8B H 0.856998 0.466974 0.405075 0.056 Uiso 1 1 calc R U . . . C8A C 0.5160(4) 0.4582(2) 0.43722(8) 0.0414(5) Uani 1 1 d . . . . . C9 C 0.4833(4) 0.7678(2) 0.40424(7) 0.0381(4) Uani 1 1 d . . . . . C10 C 0.4127(4) 0.8904(2) 0.41367(9) 0.0477(5) Uani 1 1 d . . . . . H10A H 0.270025 0.906306 0.431980 0.057 Uiso 1 1 calc R U . . . C11 C 0.5538(5) 0.9893(2) 0.39594(10) 0.0584(6) Uani 1 1 d . . . . . H11A H 0.504617 1.070883 0.402347 0.070 Uiso 1 1 calc R U . . . C12 C 0.7664(5) 0.9672(3) 0.36889(11) 0.0604(6) Uani 1 1 d . . . . . H12A H 0.860724 1.033324 0.356993 0.072 Uiso 1 1 calc R U . . . C13 C 0.8369(4) 0.8461(3) 0.35975(9) 0.0546(6) Uani 1 1 d . . . . . H13A H 0.981052 0.830605 0.341899 0.066 Uiso 1 1 calc R U . . . C14 C 0.6975(4) 0.7478(2) 0.37662(8) 0.0439(5) Uani 1 1 d . . . . . H14A H 0.746932 0.666609 0.369478 0.053 Uiso 1 1 calc R U . . . C15 C 0.3531(4) 0.3569(3) 0.45961(10) 0.0548(6) Uani 1 1 d . . . . . H15A H 0.294739 0.304073 0.432526 0.082 Uiso 1 1 calc R U . . . H15B H 0.216403 0.394692 0.476750 0.082 Uiso 1 1 calc R U . . . H15C H 0.445186 0.308097 0.483673 0.082 Uiso 1 1 calc R U . . . C16 C 0.6551(5) 0.3602(3) 0.23363(9) 0.0553(6) Uani 1 1 d . . . . . H16A H 0.613332 0.358572 0.197891 0.083 Uiso 1 1 calc R U . . . H16B H 0.747131 0.286824 0.242127 0.083 Uiso 1 1 calc R U . . . H16C H 0.751711 0.432998 0.240739 0.083 Uiso 1 1 calc R U . . . C17 C 0.3104(6) 0.2013(2) 0.27522(12) 0.0631(7) Uani 1 1 d . . . . . H17A H 0.276957 0.169736 0.241497 0.095 Uiso 1 1 calc R U . . . H17B H 0.169544 0.189165 0.296652 0.095 Uiso 1 1 calc R U . . . H17C H 0.447581 0.157587 0.289553 0.095 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0486(3) 0.0439(3) 0.0420(3) -0.0083(2) -0.0004(2) 0.0052(2) O1 0.0553(8) 0.0603(10) 0.0367(7) 0.0014(7) -0.0108(7) -0.0014(8) O2 0.0533(8) 0.0469(8) 0.0383(7) -0.0022(6) -0.0080(6) 0.0155(7) O3 0.0578(8) 0.0490(9) 0.0687(10) -0.0017(8) 0.0043(8) 0.0203(8) C2 0.0600(12) 0.0542(12) 0.0341(10) -0.0027(9) 0.0011(9) -0.0038(12) C3 0.0411(9) 0.0432(11) 0.0333(9) -0.0031(8) 0.0018(8) 0.0022(8) N4 0.0412(7) 0.0370(8) 0.0327(8) 0.0000(6) -0.0033(7) 0.0017(7) C5 0.0349(8) 0.0370(9) 0.0349(9) 0.0011(8) -0.0003(7) 0.0005(8) C6 0.0411(9) 0.0390(10) 0.0422(10) -0.0025(8) -0.0014(8) 0.0046(8) C7 0.0404(9) 0.0373(10) 0.0500(11) 0.0029(9) 0.0037(8) 0.0052(8) C8 0.0382(9) 0.0500(12) 0.0513(12) 0.0076(10) -0.0086(9) 0.0042(9) C8A 0.0408(9) 0.0468(11) 0.0366(10) 0.0054(9) -0.0083(8) -0.0014(9) C9 0.0407(9) 0.0417(10) 0.0318(9) -0.0019(8) -0.0024(8) 0.0016(9) C10 0.0543(11) 0.0444(12) 0.0444(11) -0.0038(9) 0.0009(9) 0.0050(10) C11 0.0748(16) 0.0409(12) 0.0595(15) 0.0001(11) -0.0081(13) -0.0010(12) C12 0.0603(13) 0.0539(15) 0.0671(16) 0.0126(12) -0.0047(13) -0.0118(12) C13 0.0445(11) 0.0638(15) 0.0554(13) 0.0107(11) 0.0030(10) -0.0036(11) C14 0.0413(9) 0.0458(12) 0.0446(11) 0.0022(9) 0.0019(8) 0.0024(9) C15 0.0526(12) 0.0543(13) 0.0575(13) 0.0177(11) -0.0021(10) -0.0004(12) C16 0.0612(13) 0.0565(13) 0.0483(12) -0.0051(12) 0.0093(11) 0.0007(12) C17 0.0688(14) 0.0520(14) 0.0686(16) -0.0124(12) 0.0034(14) -0.0103(12) _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C6 1.725(2) . ? S1 C17 1.794(3) . ? S1 C16 1.800(2) . ? O1 C8A 1.427(3) . ? O1 C2 1.432(3) . ? O2 C5 1.235(2) . ? O3 C7 1.239(3) . ? C2 C3 1.531(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N4 1.456(3) . ? C3 C9 1.514(3) . ? C3 H3A 0.9800 . ? N4 C5 1.367(2) . ? N4 C8A 1.470(3) . ? C5 C6 1.451(3) . ? C6 C7 1.413(3) . ? C7 C8 1.520(3) . ? C8 C8A 1.511(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8A C15 1.521(3) . ? C9 C14 1.391(3) . ? C9 C10 1.392(3) . ? C10 C11 1.390(4) . ? C10 H10A 0.9300 . ? C11 C12 1.380(4) . ? C11 H11A 0.9300 . ? C12 C13 1.375(4) . ? C12 H12A 0.9300 . ? C13 C14 1.373(3) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 S1 C17 105.82(13) . . ? C6 S1 C16 106.38(11) . . ? C17 S1 C16 100.44(13) . . ? C8A O1 C2 105.59(16) . . ? O1 C2 C3 104.13(16) . . ? O1 C2 H2A 110.9 . . ? C3 C2 H2A 110.9 . . ? O1 C2 H2B 110.9 . . ? C3 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? N4 C3 C9 114.44(16) . . ? N4 C3 C2 99.69(17) . . ? C9 C3 C2 111.85(17) . . ? N4 C3 H3A 110.1 . . ? C9 C3 H3A 110.1 . . ? C2 C3 H3A 110.1 . . ? C5 N4 C3 123.56(17) . . ? C5 N4 C8A 123.83(17) . . ? C3 N4 C8A 111.54(16) . . ? O2 C5 N4 120.25(18) . . ? O2 C5 C6 124.97(18) . . ? N4 C5 C6 114.78(18) . . ? C7 C6 C5 124.21(19) . . ? C7 C6 S1 121.06(16) . . ? C5 C6 S1 114.35(15) . . ? O3 C7 C6 124.9(2) . . ? O3 C7 C8 119.19(19) . . ? C6 C7 C8 115.84(19) . . ? C8A C8 C7 112.44(17) . . ? C8A C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? C8A C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? O1 C8A N4 102.74(16) . . ? O1 C8A C8 110.00(17) . . ? N4 C8A C8 110.38(16) . . ? O1 C8A C15 110.59(19) . . ? N4 C8A C15 111.47(16) . . ? C8 C8A C15 111.4(2) . . ? C14 C9 C10 118.1(2) . . ? C14 C9 C3 122.54(19) . . ? C10 C9 C3 119.30(18) . . ? C11 C10 C9 120.5(2) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? C13 C12 C11 119.2(2) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C14 C13 C12 120.9(2) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C13 C14 C9 120.9(2) . . ? C13 C14 H14A 119.5 . . ? C9 C14 H14A 119.5 . . ? C8A C15 H15A 109.5 . . ? C8A C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8A C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S1 C16 H16A 109.5 . . ? S1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? S1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? S1 C17 H17A 109.5 . . ? S1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? S1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8A O1 C2 C3 -41.9(2) . . . . ? O1 C2 C3 N4 31.8(2) . . . . ? O1 C2 C3 C9 -89.5(2) . . . . ? C9 C3 N4 C5 -60.9(2) . . . . ? C2 C3 N4 C5 179.65(18) . . . . ? C9 C3 N4 C8A 107.68(18) . . . . ? C2 C3 N4 C8A -11.8(2) . . . . ? C3 N4 C5 O2 -18.6(3) . . . . ? C8A N4 C5 O2 174.29(19) . . . . ? C3 N4 C5 C6 160.33(18) . . . . ? C8A N4 C5 C6 -6.8(3) . . . . ? O2 C5 C6 C7 162.5(2) . . . . ? N4 C5 C6 C7 -16.3(3) . . . . ? O2 C5 C6 S1 -10.5(3) . . . . ? N4 C5 C6 S1 170.70(14) . . . . ? C17 S1 C6 C7 58.1(2) . . . . ? C16 S1 C6 C7 -48.1(2) . . . . ? C17 S1 C6 C5 -128.66(17) . . . . ? C16 S1 C6 C5 125.11(17) . . . . ? C5 C6 C7 O3 -174.1(2) . . . . ? S1 C6 C7 O3 -1.6(3) . . . . ? C5 C6 C7 C8 3.6(3) . . . . ? S1 C6 C7 C8 176.17(15) . . . . ? O3 C7 C8 C8A -152.6(2) . . . . ? C6 C7 C8 C8A 29.5(3) . . . . ? C2 O1 C8A N4 33.3(2) . . . . ? C2 O1 C8A C8 150.84(18) . . . . ? C2 O1 C8A C15 -85.7(2) . . . . ? C5 N4 C8A O1 156.18(17) . . . . ? C3 N4 C8A O1 -12.3(2) . . . . ? C5 N4 C8A C8 38.9(3) . . . . ? C3 N4 C8A C8 -129.58(18) . . . . ? C5 N4 C8A C15 -85.4(2) . . . . ? C3 N4 C8A C15 106.1(2) . . . . ? C7 C8 C8A O1 -160.80(18) . . . . ? C7 C8 C8A N4 -48.1(2) . . . . ? C7 C8 C8A C15 76.2(2) . . . . ? N4 C3 C9 C14 -20.1(3) . . . . ? C2 C3 C9 C14 92.3(2) . . . . ? N4 C3 C9 C10 163.15(19) . . . . ? C2 C3 C9 C10 -84.4(2) . . . . ? C14 C9 C10 C11 -0.2(3) . . . . ? C3 C9 C10 C11 176.7(2) . . . . ? C9 C10 C11 C12 -0.2(4) . . . . ? C10 C11 C12 C13 -0.1(4) . . . . ? C11 C12 C13 C14 0.8(4) . . . . ? C12 C13 C14 C9 -1.2(4) . . . . ? C10 C9 C14 C13 0.9(3) . . . . ? C3 C9 C14 C13 -175.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C16 H16B O3 0.96 2.55 3.030(3) 110.8 . yes C17 H17B O3 0.96 2.49 3.371(4) 152.4 1_455 yes C17 H17C O3 0.96 2.54 3.172(4) 123.6 . yes _refine_diff_density_max 0.195 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.036 _shelx_res_file ; TITL enr33_1_a.res in P2(1)2(1)2(1) ENR33_1.res created by SHELXL-2018/1 at 09:31:20 on 13-Feb-2018 CELL 0.56083 5.4649 10.7205 26.0834 90 90 90 ZERR 4 0.0001 0.0004 0.0007 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O S UNIT 64 76 4 12 4 TEMP 22 SIZE 0.4 0.3 0.3 ACTA L.S. 20 PLAN 20 BOND $H CONF HTAB FMAP 2 EQIV $1 x-1, y, z HTAB C16 O3 HTAB C17 O3_$1 HTAB C17 O3 WGHT 0.059800 EXTI 0.039116 FVAR 0.90225 S1 5 0.379531 0.364608 0.271416 11.00000 0.04864 0.04390 = 0.04204 -0.00832 -0.00041 0.00516 O1 4 0.597435 0.541066 0.476472 11.00000 0.05525 0.06025 = 0.03666 0.00140 -0.01077 -0.00144 O2 4 0.204401 0.585772 0.326521 11.00000 0.05333 0.04694 = 0.03826 -0.00217 -0.00798 0.01553 O3 4 0.788506 0.263743 0.339200 11.00000 0.05781 0.04896 = 0.06875 -0.00173 0.00432 0.02030 C2 1 0.407856 0.632397 0.481735 11.00000 0.06002 0.05418 = 0.03411 -0.00273 0.00111 -0.00376 AFIX 23 H2A 2 0.468312 0.706395 0.498983 11.00000 -1.20000 H2B 2 0.270629 0.599097 0.500945 11.00000 -1.20000 AFIX 0 C3 1 0.333360 0.662081 0.426471 11.00000 0.04105 0.04322 = 0.03330 -0.00313 0.00183 0.00219 AFIX 13 H3A 2 0.158693 0.682430 0.424905 11.00000 -1.20000 AFIX 0 N4 3 0.378178 0.541160 0.402868 11.00000 0.04117 0.03701 = 0.03270 -0.00003 -0.00328 0.00173 C5 1 0.338044 0.516779 0.352121 11.00000 0.03491 0.03704 = 0.03489 0.00110 -0.00031 0.00047 C6 1 0.466269 0.408425 0.332390 11.00000 0.04108 0.03899 = 0.04216 -0.00252 -0.00137 0.00457 C7 1 0.665285 0.350120 0.357360 11.00000 0.04035 0.03729 = 0.04997 0.00294 0.00372 0.00522 C8 1 0.733351 0.402963 0.409513 11.00000 0.03816 0.04998 = 0.05125 0.00758 -0.00856 0.00423 AFIX 23 H8A 2 0.803469 0.337125 0.430368 11.00000 -1.20000 H8B 2 0.856998 0.466974 0.405075 11.00000 -1.20000 AFIX 0 C8A 1 0.515995 0.458197 0.437222 11.00000 0.04080 0.04685 = 0.03662 0.00540 -0.00835 -0.00143 C9 1 0.483302 0.767834 0.404242 11.00000 0.04066 0.04166 = 0.03184 -0.00187 -0.00236 0.00156 C10 1 0.412694 0.890417 0.413674 11.00000 0.05428 0.04436 = 0.04437 -0.00377 0.00092 0.00504 AFIX 43 H10A 2 0.270025 0.906306 0.431980 11.00000 -1.20000 AFIX 0 C11 1 0.553806 0.989313 0.395939 11.00000 0.07479 0.04095 = 0.05952 0.00005 -0.00811 -0.00098 AFIX 43 H11A 2 0.504617 1.070883 0.402347 11.00000 -1.20000 AFIX 0 C12 1 0.766369 0.967187 0.368891 11.00000 0.06025 0.05387 = 0.06710 0.01259 -0.00469 -0.01183 AFIX 43 H12A 2 0.860724 1.033324 0.356993 11.00000 -1.20000 AFIX 0 C13 1 0.836919 0.846117 0.359751 11.00000 0.04450 0.06384 = 0.05541 0.01067 0.00304 -0.00356 AFIX 43 H13A 2 0.981052 0.830605 0.341899 11.00000 -1.20000 AFIX 0 C14 1 0.697480 0.747775 0.376621 11.00000 0.04128 0.04582 = 0.04456 0.00221 0.00192 0.00242 AFIX 43 H14A 2 0.746932 0.666609 0.369478 11.00000 -1.20000 AFIX 0 C15 1 0.353063 0.356931 0.459606 11.00000 0.05257 0.05429 = 0.05754 0.01773 -0.00210 -0.00040 AFIX 137 H15A 2 0.294739 0.304073 0.432526 11.00000 -1.50000 H15B 2 0.216403 0.394692 0.476750 11.00000 -1.50000 H15C 2 0.445186 0.308097 0.483673 11.00000 -1.50000 AFIX 0 C16 1 0.655079 0.360241 0.233635 11.00000 0.06118 0.05649 = 0.04828 -0.00509 0.00928 0.00068 AFIX 137 H16A 2 0.613332 0.358572 0.197891 11.00000 -1.50000 H16B 2 0.747131 0.286824 0.242127 11.00000 -1.50000 H16C 2 0.751711 0.432998 0.240739 11.00000 -1.50000 AFIX 0 C17 1 0.310365 0.201295 0.275222 11.00000 0.06881 0.05204 = 0.06859 -0.01243 0.00338 -0.01029 AFIX 137 H17A 2 0.276957 0.169736 0.241497 11.00000 -1.50000 H17B 2 0.169544 0.189165 0.296652 11.00000 -1.50000 H17C 2 0.447581 0.157587 0.289553 11.00000 -1.50000 AFIX 0 HKLF 4 REM enr33_1_a.res in P2(1)2(1)2(1) REM R1 = 0.0312 for 3073 Fo > 4sig(Fo) and 0.0342 for all 3324 data REM 194 parameters refined using 0 restraints END WGHT 0.0595 0.0000 REM Instructions for potential hydrogen bonds HTAB C16 O3 HTAB C17 O3_$1 HTAB C17 O3 REM Highest difference peak 0.195, deepest hole -0.193, 1-sigma level 0.036 Q1 1 0.7944 0.3642 0.2601 11.00000 0.05 0.20 Q2 1 0.2307 0.4185 0.2474 11.00000 0.05 0.16 Q3 1 0.5247 0.3503 0.2461 11.00000 0.05 0.15 Q4 1 0.6037 0.2861 0.2010 11.00000 0.05 0.15 Q5 1 0.5068 0.3771 0.3034 11.00000 0.05 0.13 Q6 1 0.2041 0.3229 0.2505 11.00000 0.05 0.13 Q7 1 0.7325 0.5422 0.5097 11.00000 0.05 0.12 Q8 1 0.1223 0.2188 0.2420 11.00000 0.05 0.11 Q9 1 0.2372 0.2861 0.2699 11.00000 0.05 0.11 Q10 1 0.2521 0.3827 0.3050 11.00000 0.05 0.11 Q11 1 0.4247 0.1776 0.3046 11.00000 0.05 0.11 Q12 1 0.9626 0.8250 0.3144 11.00000 0.05 0.11 Q13 1 0.2139 0.3917 0.4907 11.00000 0.05 0.10 Q14 1 0.5628 0.3702 0.3432 11.00000 0.05 0.10 Q15 1 0.8469 0.4015 0.3782 11.00000 0.05 0.10 Q16 1 0.6622 0.2469 0.3140 11.00000 0.05 0.10 Q17 1 0.5444 0.6458 0.5100 11.00000 0.05 0.10 Q18 1 0.0967 0.1416 0.2620 11.00000 0.05 0.10 Q19 1 0.7401 0.6431 0.3436 11.00000 0.05 0.10 Q20 1 0.3337 0.5641 0.2972 11.00000 0.05 0.10 ; _shelx_res_checksum 79980 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_32a _database_code_depnum_ccdc_archive 'CCDC 2125369' loop_ _audit_author_name _audit_author_address 'Sylvain Bernes' ;Instituto de Fisica, BUAP, Puebla Mexico ; _audit_update_record ; 2021-11-30 deposited with the CCDC. 2022-01-21 downloaded from the CCDC. ; # Clave Lab. : ENR-194-2 # Clave IF-UAP: ENR194_2 # Solicitud: 160 # Firma en la Solicitud: Dr. Joel Teran (ICUAP) # Clave datos : ... \BUAP\Sylvain\ENR194_2\40mm_2\ _database_code_CAS ? _database_code_CSD ? _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _audit_creation_date 2018-09-10 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H17 N O3' _chemical_formula_sum 'C14 H17 N O3' _chemical_formula_weight 247.28 _chemical_absolute_configuration syn _chemical_optical_rotation ? _chemical_properties_physical ? _chemical_properties_biological ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 21' _space_group_name_Hall 'P 2yb' _shelx_space_group_comment ? loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.5839(15) _cell_length_b 6.9820(5) _cell_length_c 16.333(2) _cell_angle_alpha 90 _cell_angle_beta 102.429(10) _cell_angle_gamma 90 _cell_volume 1290.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 7259 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 25.51 _exptl_crystal_recrystallization_method ; Re-crystallisation from solvent: CH2Cl2/Petroleum benzine ; _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_F_000 528 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.040 _exptl_absorpt_coefficient_mu 0.056 _shelx_estimated_absorpt_T_min 0.982 _shelx_estimated_absorpt_T_max 0.998 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3987 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'X-AREA 1.82 (Stoe & Cie, 2018)' _diffrn_ambient_temperature 295(1) _diffrn_ambient_environment air _diffrn_measurement_specimen_support Mitegen _diffrn_source 'Sealed X-ray tube' _diffrn_source_type 'Axo Astix-f Microfocus source' _diffrn_source_voltage 65 _diffrn_source_current 0.600 _diffrn_source_power 0.039 _diffrn_radiation_collimation '0.6 mm diameter' _diffrn_radiation_probe x-ray _diffrn_radiation_type AgK\a _diffrn_radiation_wavelength 0.56083 _diffrn_radiation_monochromator 'Graded multilayer mirror' _diffrn_radiation_polarisn_norm -90 _diffrn_measurement_device 'Eulerian four-circle diffractometer' _diffrn_measurement_device_type 'Stoe Stadivari' _diffrn_detector 'Reverse-biased silicon diode array' _diffrn_detector_type 'Dectris Pilatus 100K R' _diffrn_measurement_method '\w scans' _diffrn_measurement_details ; 1148 frames, 70 s/frame, 1 deg./frame, detector distance = 40 mm ; _diffrn_detector_area_resol_mean 5.81 _diffrn_reflns_number 29502 _diffrn_reflns_av_unetI/netI 0.2294 _diffrn_reflns_av_R_equivalents 0.1823 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.513 _diffrn_reflns_theta_max 20.988 _diffrn_reflns_theta_full 19.664 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.955 _diffrn_reflns_point_group_measured_fraction_full 0.953 _reflns_number_total 5371 _reflns_number_gt 1684 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.767 _reflns_Friedel_fraction_max 0.905 _reflns_Friedel_fraction_full 0.901 _reflns_special_details ? _computing_data_collection 'X-AREA 1.82 (Stoe & Cie, 2018)' _computing_cell_refinement 'X-AREA 1.82' _computing_data_reduction 'X-AREA 1.82' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015a)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)' _computing_publication_material 'PublCif (Westrip, 2010)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0405P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? # -0.3(10) _refine_ls_number_reflns 5371 _refine_ls_number_parameters 329 _refine_ls_number_restraints 1 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1941 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 0.713 _refine_ls_restrained_S_all 0.713 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5626(4) 0.0545(6) 0.7943(3) 0.0675(14) Uani 1 1 d . . . . . C2 C 0.4553(7) 0.0007(8) 0.8152(4) 0.074(2) Uani 1 1 d . . . . . H2A H 0.465038 -0.013181 0.875397 0.089 Uiso 1 1 calc R U . . . H2B H 0.426610 -0.119344 0.788472 0.089 Uiso 1 1 calc R U . . . C3 C 0.3687(6) 0.1676(8) 0.7817(4) 0.0538(18) Uani 1 1 d . . . . . H3A H 0.289243 0.116655 0.759749 0.065 Uiso 1 1 calc R U . . . N4 N 0.4206(4) 0.2304(7) 0.7131(3) 0.0443(13) Uani 1 1 d . . . . . C5 C 0.3748(6) 0.3675(9) 0.6588(4) 0.0518(17) Uani 1 1 d . . . . . O5 O 0.2787(4) 0.4408(6) 0.6598(2) 0.0703(13) Uani 1 1 d . . . . . C6 C 0.4478(6) 0.4198(10) 0.5958(4) 0.0628(18) Uani 1 1 d . . . . . H6A H 0.426361 0.548544 0.575905 0.075 Uiso 1 1 calc R U . . . H6B H 0.426260 0.334258 0.548193 0.075 Uiso 1 1 calc R U . . . C7 C 0.5817(6) 0.4121(11) 0.6269(4) 0.071(2) Uani 1 1 d . . . . . H7A H 0.609340 0.541503 0.644329 0.085 Uiso 1 1 calc R U . . . O7 O 0.6297(4) 0.3602(10) 0.5573(3) 0.0915(16) Uani 1 1 d . . . . . H7 H 0.701735 0.350955 0.572138 0.137 Uiso 1 1 calc R U . . . C8 C 0.6219(6) 0.2789(10) 0.7007(4) 0.070(2) Uani 1 1 d . . . . . H8A H 0.641981 0.355411 0.751329 0.084 Uiso 1 1 calc R U . . . H8B H 0.693311 0.214325 0.693797 0.084 Uiso 1 1 calc R U . . . C8A C 0.5325(6) 0.1287(8) 0.7126(4) 0.0557(18) Uani 1 1 d . . . . . C9 C 0.3645(6) 0.3146(8) 0.8472(4) 0.0467(16) Uani 1 1 d . . . . . C10 C 0.4542(6) 0.4486(9) 0.8731(4) 0.0532(16) Uani 1 1 d . . . . . H10A H 0.517155 0.453973 0.846238 0.064 Uiso 1 1 calc R U . . . C11 C 0.4508(7) 0.5733(9) 0.9382(4) 0.064(2) Uani 1 1 d . . . . . H11A H 0.511219 0.661643 0.955337 0.077 Uiso 1 1 calc R U . . . C12 C 0.3561(8) 0.5651(11) 0.9776(4) 0.073(2) Uani 1 1 d . . . . . H12A H 0.353534 0.648462 1.021543 0.088 Uiso 1 1 calc R U . . . C13 C 0.2687(7) 0.4392(13) 0.9532(5) 0.077(2) Uani 1 1 d . . . . . H13A H 0.205065 0.436490 0.979603 0.092 Uiso 1 1 calc R U . . . C14 C 0.2730(6) 0.3137(9) 0.8891(4) 0.0588(19) Uani 1 1 d . . . . . H14A H 0.212198 0.225228 0.873464 0.071 Uiso 1 1 calc R U . . . C15 C 0.5161(7) -0.0297(10) 0.6470(4) 0.091(2) Uani 1 1 d . . . . . H15A H 0.461612 -0.123241 0.659435 0.136 Uiso 1 1 calc R U . . . H15B H 0.590883 -0.089738 0.647689 0.136 Uiso 1 1 calc R U . . . H15C H 0.485549 0.024023 0.592559 0.136 Uiso 1 1 calc R U . . . O21 O 1.0900(4) 0.9386(5) 0.7543(3) 0.0599(12) Uani 1 1 d . . . . . C22 C 1.1324(6) 0.7604(9) 0.7916(4) 0.068(2) Uani 1 1 d . . . . . H22A H 1.138867 0.764236 0.851736 0.081 Uiso 1 1 calc R U . . . H22B H 1.209441 0.730858 0.780470 0.081 Uiso 1 1 calc R U . . . C23 C 1.0405(5) 0.6104(8) 0.7508(4) 0.0503(17) Uani 1 1 d . . . . . H23A H 1.080003 0.492317 0.739341 0.060 Uiso 1 1 calc R U . . . N24 N 0.9884(4) 0.7078(6) 0.6725(3) 0.0466(14) Uani 1 1 d . . . . . C25 C 0.8942(6) 0.6402(9) 0.6188(4) 0.0514(17) Uani 1 1 d . . . . . O25 O 0.8562(4) 0.4771(5) 0.6253(3) 0.0637(13) Uani 1 1 d . . . . . C26 C 0.8296(7) 0.7742(8) 0.5536(4) 0.084(3) Uani 1 1 d . . . . . H26A H 0.835336 0.723127 0.499347 0.100 Uiso 1 1 calc R U . . . H26B H 0.746727 0.769815 0.556130 0.100 Uiso 1 1 calc R U . . . C27 C 0.8645(7) 0.9777(10) 0.5553(4) 0.069(2) Uani 1 1 d . . . . . H27A H 0.793292 1.057635 0.545910 0.083 Uiso 1 1 calc R U . . . O27 O 0.9186(7) 0.9952(12) 0.4856(4) 0.161(3) Uani 1 1 d . . . . . H27 H 0.880137 0.935075 0.445783 0.242 Uiso 1 1 calc R U . . . C28 C 0.9472(6) 1.0420(8) 0.6330(4) 0.064(2) Uani 1 1 d . . . . . H28A H 0.902353 1.069653 0.675303 0.077 Uiso 1 1 calc R U . . . H28B H 0.984742 1.160113 0.621210 0.077 Uiso 1 1 calc R U . . . C28A C 1.0423(6) 0.8970(8) 0.6679(4) 0.0478(16) Uani 1 1 d . . . . . C29 C 0.9506(6) 0.5675(10) 0.8038(4) 0.0590(19) Uani 1 1 d . . . . . C30 C 0.8719(8) 0.7039(11) 0.8173(5) 0.082(2) Uani 1 1 d . . . . . H30A H 0.869760 0.821275 0.790015 0.098 Uiso 1 1 calc R U . . . C31 C 0.7937(8) 0.6711(15) 0.8715(6) 0.103(3) Uani 1 1 d . . . . . H31A H 0.740181 0.765189 0.879249 0.123 Uiso 1 1 calc R U . . . C32 C 0.7976(10) 0.5014(18) 0.9119(6) 0.113(4) Uani 1 1 d . . . . . H32A H 0.748007 0.479557 0.948743 0.135 Uiso 1 1 calc R U . . . C33 C 0.8758(8) 0.3596(16) 0.8985(6) 0.105(3) Uani 1 1 d . . . . . H33A H 0.878164 0.242626 0.926019 0.126 Uiso 1 1 calc R U . . . C34 C 0.9510(6) 0.3936(11) 0.8431(5) 0.082(2) Uani 1 1 d . . . . . H34A H 1.001587 0.297298 0.832965 0.099 Uiso 1 1 calc R U . . . C35 C 1.1420(5) 0.8884(8) 0.6200(4) 0.0594(18) Uani 1 1 d . . . . . H35A H 1.195496 0.786799 0.642194 0.089 Uiso 1 1 calc R U . . . H35B H 1.183894 1.008032 0.626139 0.089 Uiso 1 1 calc R U . . . H35C H 1.109332 0.865092 0.561731 0.089 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.068(4) 0.060(3) 0.068(3) 0.018(3) 0.002(3) 0.020(3) C2 0.110(7) 0.036(4) 0.069(5) 0.011(3) 0.005(5) 0.002(4) C3 0.055(5) 0.054(4) 0.048(4) -0.009(3) 0.002(4) -0.010(4) N4 0.043(3) 0.044(3) 0.044(3) -0.001(3) 0.006(3) 0.002(3) C5 0.051(5) 0.052(4) 0.043(4) 0.000(3) -0.009(4) 0.004(4) O5 0.058(3) 0.085(3) 0.064(3) 0.012(3) 0.003(3) 0.032(3) C6 0.062(5) 0.070(5) 0.054(4) 0.002(4) 0.007(4) 0.000(4) C7 0.055(5) 0.092(6) 0.061(5) -0.021(5) 0.006(4) -0.006(4) O7 0.059(3) 0.141(4) 0.078(4) -0.011(3) 0.021(3) -0.008(4) C8 0.045(5) 0.099(6) 0.064(5) -0.003(5) 0.006(4) 0.009(4) C8A 0.053(5) 0.047(4) 0.063(5) 0.003(4) 0.004(4) 0.017(4) C9 0.043(4) 0.051(4) 0.042(4) 0.007(3) 0.001(4) 0.001(3) C10 0.059(5) 0.051(3) 0.048(4) -0.002(4) 0.009(3) -0.007(4) C11 0.083(6) 0.044(3) 0.055(5) -0.004(4) -0.007(4) 0.001(4) C12 0.090(7) 0.082(5) 0.041(4) -0.005(4) 0.002(5) 0.025(5) C13 0.062(6) 0.100(6) 0.067(5) 0.013(5) 0.013(5) 0.017(5) C14 0.056(5) 0.056(4) 0.061(5) 0.006(4) 0.005(4) 0.004(4) C15 0.112(7) 0.066(4) 0.092(6) -0.018(5) 0.018(5) 0.017(5) O21 0.064(3) 0.052(2) 0.057(3) -0.001(2) -0.004(2) -0.011(2) C22 0.052(5) 0.069(5) 0.072(5) 0.017(4) -0.009(4) -0.006(4) C23 0.035(4) 0.052(4) 0.063(4) 0.006(3) 0.008(4) -0.003(3) N24 0.043(3) 0.037(3) 0.053(3) 0.000(3) -0.004(3) 0.002(3) C25 0.048(5) 0.050(4) 0.054(4) -0.004(4) 0.007(4) 0.007(4) O25 0.053(3) 0.042(2) 0.090(4) -0.005(3) 0.003(3) -0.012(2) C26 0.102(6) 0.058(4) 0.070(5) 0.006(4) -0.027(5) -0.016(4) C27 0.081(6) 0.062(5) 0.067(6) 0.012(4) 0.021(5) 0.011(4) O27 0.172(7) 0.170(7) 0.113(5) 0.034(5) -0.033(5) -0.092(5) C28 0.067(5) 0.046(4) 0.070(5) -0.016(4) -0.006(4) 0.014(4) C28A 0.051(4) 0.040(4) 0.048(4) 0.001(3) 0.001(3) -0.002(3) C29 0.056(5) 0.059(4) 0.055(5) 0.000(4) -0.004(4) -0.011(4) C30 0.097(7) 0.065(5) 0.088(6) -0.003(5) 0.030(5) -0.002(5) C31 0.094(8) 0.134(8) 0.091(7) -0.021(6) 0.043(6) -0.006(6) C32 0.094(9) 0.158(10) 0.090(7) 0.017(7) 0.025(6) -0.033(8) C33 0.069(7) 0.135(8) 0.104(8) 0.060(7) 0.002(6) -0.040(6) C34 0.056(5) 0.086(6) 0.099(6) 0.027(5) 0.004(5) -0.016(4) C35 0.049(4) 0.059(4) 0.069(5) 0.014(4) 0.008(4) -0.002(3) _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8A 1.403(7) . ? O1 C2 1.409(8) . ? C2 C3 1.558(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N4 1.449(7) . ? C3 C9 1.490(8) . ? C3 H3A 0.9800 . ? N4 C5 1.335(7) . ? N4 C8A 1.480(7) . ? C5 O5 1.229(7) . ? C5 C6 1.509(8) . ? C6 C7 1.526(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O7 1.416(7) . ? C7 C8 1.514(8) . ? C7 H7A 0.9800 . ? O7 H7 0.8200 . ? C8 C8A 1.515(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8A C15 1.523(8) . ? C9 C14 1.380(8) . ? C9 C10 1.394(7) . ? C10 C11 1.381(8) . ? C10 H10A 0.9300 . ? C11 C12 1.387(9) . ? C11 H11A 0.9300 . ? C12 C13 1.336(10) . ? C12 H12A 0.9300 . ? C13 C14 1.375(9) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? O21 C22 1.425(6) . ? O21 C28A 1.432(6) . ? C22 C23 1.539(7) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 N24 1.459(7) . ? C23 C29 1.521(8) . ? C23 H23A 0.9800 . ? N24 C25 1.331(7) . ? N24 C28A 1.470(7) . ? C25 O25 1.234(7) . ? C25 C26 1.492(8) . ? C26 C27 1.476(8) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 O27 1.419(8) . ? C27 C28 1.486(8) . ? C27 H27A 0.9800 . ? O27 H27 0.8200 . ? C28 C28A 1.514(7) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28A C35 1.528(8) . ? C29 C30 1.369(9) . ? C29 C34 1.373(9) . ? C30 C31 1.416(9) . ? C30 H30A 0.9300 . ? C31 C32 1.352(11) . ? C31 H31A 0.9300 . ? C32 C33 1.391(11) . ? C32 H32A 0.9300 . ? C33 C34 1.404(10) . ? C33 H33A 0.9300 . ? C34 H34A 0.9300 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8A O1 C2 106.1(5) . . ? O1 C2 C3 104.5(5) . . ? O1 C2 H2A 110.9 . . ? C3 C2 H2A 110.9 . . ? O1 C2 H2B 110.9 . . ? C3 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? N4 C3 C9 115.5(5) . . ? N4 C3 C2 98.9(5) . . ? C9 C3 C2 112.4(5) . . ? N4 C3 H3A 109.9 . . ? C9 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? C5 N4 C3 124.1(6) . . ? C5 N4 C8A 124.3(6) . . ? C3 N4 C8A 111.7(5) . . ? O5 C5 N4 121.4(7) . . ? O5 C5 C6 123.4(6) . . ? N4 C5 C6 115.2(6) . . ? C5 C6 C7 116.3(5) . . ? C5 C6 H6A 108.2 . . ? C7 C6 H6A 108.2 . . ? C5 C6 H6B 108.2 . . ? C7 C6 H6B 108.2 . . ? H6A C6 H6B 107.4 . . ? O7 C7 C8 112.0(6) . . ? O7 C7 C6 106.8(5) . . ? C8 C7 C6 113.7(6) . . ? O7 C7 H7A 108.0 . . ? C8 C7 H7A 108.0 . . ? C6 C7 H7A 108.0 . . ? C7 O7 H7 109.5 . . ? C7 C8 C8A 115.2(6) . . ? C7 C8 H8A 108.5 . . ? C8A C8 H8A 108.5 . . ? C7 C8 H8B 108.5 . . ? C8A C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? O1 C8A N4 102.2(5) . . ? O1 C8A C8 109.9(6) . . ? N4 C8A C8 107.0(5) . . ? O1 C8A C15 111.6(5) . . ? N4 C8A C15 112.0(5) . . ? C8 C8A C15 113.4(6) . . ? C14 C9 C10 117.0(6) . . ? C14 C9 C3 120.0(6) . . ? C10 C9 C3 122.9(6) . . ? C11 C10 C9 121.0(6) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C10 C11 C12 119.2(7) . . ? C10 C11 H11A 120.4 . . ? C12 C11 H11A 120.4 . . ? C13 C12 C11 120.9(7) . . ? C13 C12 H12A 119.5 . . ? C11 C12 H12A 119.5 . . ? C12 C13 C14 119.8(7) . . ? C12 C13 H13A 120.1 . . ? C14 C13 H13A 120.1 . . ? C13 C14 C9 122.2(7) . . ? C13 C14 H14A 118.9 . . ? C9 C14 H14A 118.9 . . ? C8A C15 H15A 109.5 . . ? C8A C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8A C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C22 O21 C28A 105.6(4) . . ? O21 C22 C23 105.5(5) . . ? O21 C22 H22A 110.6 . . ? C23 C22 H22A 110.6 . . ? O21 C22 H22B 110.6 . . ? C23 C22 H22B 110.6 . . ? H22A C22 H22B 108.8 . . ? N24 C23 C29 112.7(5) . . ? N24 C23 C22 100.3(5) . . ? C29 C23 C22 112.4(6) . . ? N24 C23 H23A 110.3 . . ? C29 C23 H23A 110.3 . . ? C22 C23 H23A 110.3 . . ? C25 N24 C23 122.6(5) . . ? C25 N24 C28A 125.6(5) . . ? C23 N24 C28A 111.3(5) . . ? O25 C25 N24 121.8(5) . . ? O25 C25 C26 120.4(6) . . ? N24 C25 C26 117.6(6) . . ? C27 C26 C25 119.8(6) . . ? C27 C26 H26A 107.4 . . ? C25 C26 H26A 107.4 . . ? C27 C26 H26B 107.4 . . ? C25 C26 H26B 107.4 . . ? H26A C26 H26B 106.9 . . ? O27 C27 C26 103.6(7) . . ? O27 C27 C28 110.1(6) . . ? C26 C27 C28 115.6(6) . . ? O27 C27 H27A 109.1 . . ? C26 C27 H27A 109.1 . . ? C28 C27 H27A 109.1 . . ? C27 O27 H27 109.5 . . ? C27 C28 C28A 113.7(5) . . ? C27 C28 H28A 108.8 . . ? C28A C28 H28A 108.8 . . ? C27 C28 H28B 108.8 . . ? C28A C28 H28B 108.8 . . ? H28A C28 H28B 107.7 . . ? O21 C28A N24 102.1(5) . . ? O21 C28A C28 109.3(5) . . ? N24 C28A C28 109.7(5) . . ? O21 C28A C35 109.8(5) . . ? N24 C28A C35 111.6(5) . . ? C28 C28A C35 113.7(5) . . ? C30 C29 C34 118.4(7) . . ? C30 C29 C23 121.0(7) . . ? C34 C29 C23 120.5(7) . . ? C29 C30 C31 121.7(8) . . ? C29 C30 H30A 119.1 . . ? C31 C30 H30A 119.1 . . ? C32 C31 C30 119.2(9) . . ? C32 C31 H31A 120.4 . . ? C30 C31 H31A 120.4 . . ? C31 C32 C33 120.1(10) . . ? C31 C32 H32A 119.9 . . ? C33 C32 H32A 119.9 . . ? C32 C33 C34 119.8(9) . . ? C32 C33 H33A 120.1 . . ? C34 C33 H33A 120.1 . . ? C29 C34 C33 120.7(8) . . ? C29 C34 H34A 119.7 . . ? C33 C34 H34A 119.7 . . ? C28A C35 H35A 109.5 . . ? C28A C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C28A C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8A O1 C2 C3 -42.2(6) . . . . ? O1 C2 C3 N4 28.4(6) . . . . ? O1 C2 C3 C9 -93.9(7) . . . . ? C9 C3 N4 C5 -64.1(7) . . . . ? C2 C3 N4 C5 175.8(5) . . . . ? C9 C3 N4 C8A 113.9(6) . . . . ? C2 C3 N4 C8A -6.3(6) . . . . ? C3 N4 C5 O5 -5.7(9) . . . . ? C8A N4 C5 O5 176.6(5) . . . . ? C3 N4 C5 C6 175.9(5) . . . . ? C8A N4 C5 C6 -1.8(8) . . . . ? O5 C5 C6 C7 146.7(6) . . . . ? N4 C5 C6 C7 -34.9(8) . . . . ? C5 C6 C7 O7 148.4(6) . . . . ? C5 C6 C7 C8 24.3(8) . . . . ? O7 C7 C8 C8A -101.2(7) . . . . ? C6 C7 C8 C8A 20.0(8) . . . . ? C2 O1 C8A N4 36.9(6) . . . . ? C2 O1 C8A C8 150.2(5) . . . . ? C2 O1 C8A C15 -83.0(6) . . . . ? C5 N4 C8A O1 160.2(5) . . . . ? C3 N4 C8A O1 -17.8(6) . . . . ? C5 N4 C8A C8 44.7(7) . . . . ? C3 N4 C8A C8 -133.3(5) . . . . ? C5 N4 C8A C15 -80.2(7) . . . . ? C3 N4 C8A C15 101.8(6) . . . . ? C7 C8 C8A O1 -162.0(5) . . . . ? C7 C8 C8A N4 -51.9(7) . . . . ? C7 C8 C8A C15 72.2(7) . . . . ? N4 C3 C9 C14 147.7(6) . . . . ? C2 C3 C9 C14 -99.9(7) . . . . ? N4 C3 C9 C10 -36.8(8) . . . . ? C2 C3 C9 C10 75.6(7) . . . . ? C14 C9 C10 C11 0.3(8) . . . . ? C3 C9 C10 C11 -175.3(6) . . . . ? C9 C10 C11 C12 -0.4(9) . . . . ? C10 C11 C12 C13 -0.2(10) . . . . ? C11 C12 C13 C14 1.0(11) . . . . ? C12 C13 C14 C9 -1.1(10) . . . . ? C10 C9 C14 C13 0.5(9) . . . . ? C3 C9 C14 C13 176.2(5) . . . . ? C28A O21 C22 C23 -39.1(6) . . . . ? O21 C22 C23 N24 23.7(6) . . . . ? O21 C22 C23 C29 -96.3(6) . . . . ? C29 C23 N24 C25 -53.1(8) . . . . ? C22 C23 N24 C25 -172.9(5) . . . . ? C29 C23 N24 C28A 119.0(6) . . . . ? C22 C23 N24 C28A -0.8(6) . . . . ? C23 N24 C25 O25 -11.4(9) . . . . ? C28A N24 C25 O25 177.7(6) . . . . ? C23 N24 C25 C26 163.9(6) . . . . ? C28A N24 C25 C26 -7.1(9) . . . . ? O25 C25 C26 C27 169.9(7) . . . . ? N24 C25 C26 C27 -5.5(10) . . . . ? C25 C26 C27 O27 108.7(8) . . . . ? C25 C26 C27 C28 -11.8(11) . . . . ? O27 C27 C28 C28A -77.2(8) . . . . ? C26 C27 C28 C28A 39.6(9) . . . . ? C22 O21 C28A N24 37.1(5) . . . . ? C22 O21 C28A C28 153.3(5) . . . . ? C22 O21 C28A C35 -81.4(6) . . . . ? C25 N24 C28A O21 150.0(6) . . . . ? C23 N24 C28A O21 -21.9(6) . . . . ? C25 N24 C28A C28 34.1(8) . . . . ? C23 N24 C28A C28 -137.8(5) . . . . ? C25 N24 C28A C35 -92.8(7) . . . . ? C23 N24 C28A C35 95.3(6) . . . . ? C27 C28 C28A O21 -160.0(5) . . . . ? C27 C28 C28A N24 -48.8(8) . . . . ? C27 C28 C28A C35 76.9(7) . . . . ? N24 C23 C29 C30 -46.1(9) . . . . ? C22 C23 C29 C30 66.4(8) . . . . ? N24 C23 C29 C34 137.4(6) . . . . ? C22 C23 C29 C34 -110.1(7) . . . . ? C34 C29 C30 C31 1.4(11) . . . . ? C23 C29 C30 C31 -175.2(6) . . . . ? C29 C30 C31 C32 0.8(13) . . . . ? C30 C31 C32 C33 -1.6(14) . . . . ? C31 C32 C33 C34 0.3(15) . . . . ? C30 C29 C34 C33 -2.6(10) . . . . ? C23 C29 C34 C33 174.0(6) . . . . ? C32 C33 C34 C29 1.8(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O7 H7 O25 0.82 2.02 2.744(6) 147.7 . yes O27 H27 O5 0.82 2.23 2.944(7) 145.0 2_656 yes _refine_diff_density_max 0.288 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.037 _shelx_res_file ; TITL enr194_2_a.res in P2(1) ENR194_2.res created by SHELXL-2018/3 at 10:32:14 on 10-Sep-2018 CELL 0.56083 11.5839 6.9820 16.3335 90.000 102.429 90.000 ZERR 4.00 0.0015 0.0005 0.0020 0.000 0.010 0.000 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O UNIT 56 68 4 12 TEMP 22 SIZE 0.32 0.15 0.04 OMIT -2 0 1 L.S. 20 PLAN 40 BOND $H CONF EQIV $2 -x+1, y+1/2, -z+1 HTAB O7 O25 HTAB O27 O5_$2 LIST 4 FMAP 2 ACTA WGHT 0.040500 FVAR 0.96389 O1 4 0.562634 0.054524 0.794296 11.00000 0.06835 0.06025 = 0.06834 0.01826 0.00208 0.02038 C2 1 0.455300 0.000679 0.815206 11.00000 0.10988 0.03617 = 0.06932 0.01111 0.00489 0.00238 AFIX 23 H2A 2 0.465038 -0.013181 0.875397 11.00000 -1.20000 H2B 2 0.426610 -0.119344 0.788472 11.00000 -1.20000 AFIX 0 C3 1 0.368694 0.167639 0.781725 11.00000 0.05511 0.05442 = 0.04772 -0.00890 0.00164 -0.01005 AFIX 13 H3A 2 0.289243 0.116655 0.759749 11.00000 -1.20000 AFIX 0 N4 3 0.420562 0.230384 0.713126 11.00000 0.04294 0.04438 = 0.04409 -0.00083 0.00606 0.00161 C5 1 0.374830 0.367497 0.658762 11.00000 0.05109 0.05223 = 0.04346 0.00022 -0.00863 0.00371 O5 4 0.278714 0.440821 0.659782 11.00000 0.05811 0.08464 = 0.06356 0.01168 0.00319 0.03169 C6 1 0.447786 0.419793 0.595837 11.00000 0.06213 0.07030 = 0.05352 0.00162 0.00712 0.00009 AFIX 23 H6A 2 0.426361 0.548544 0.575905 11.00000 -1.20000 H6B 2 0.426260 0.334258 0.548193 11.00000 -1.20000 AFIX 0 C7 1 0.581700 0.412128 0.626880 11.00000 0.05541 0.09212 = 0.06128 -0.02056 0.00612 -0.00590 AFIX 13 H7A 2 0.609340 0.541503 0.644329 11.00000 -1.20000 AFIX 0 O7 4 0.629686 0.360176 0.557298 11.00000 0.05939 0.14052 = 0.07758 -0.01124 0.02138 -0.00842 AFIX 147 H7 2 0.701735 0.350955 0.572138 11.00000 -1.50000 AFIX 0 C8 1 0.621869 0.278897 0.700687 11.00000 0.04541 0.09861 = 0.06424 -0.00286 0.00599 0.00889 AFIX 23 H8A 2 0.641981 0.355411 0.751329 11.00000 -1.20000 H8B 2 0.693311 0.214325 0.693797 11.00000 -1.20000 AFIX 0 C8A 1 0.532524 0.128714 0.712626 11.00000 0.05268 0.04743 = 0.06283 0.00296 0.00352 0.01722 C9 1 0.364493 0.314594 0.847195 11.00000 0.04347 0.05085 = 0.04216 0.00744 0.00114 0.00118 C10 1 0.454160 0.448551 0.873133 11.00000 0.05910 0.05140 = 0.04797 -0.00217 0.00917 -0.00692 AFIX 43 H10A 2 0.517155 0.453973 0.846238 11.00000 -1.20000 AFIX 0 C11 1 0.450786 0.573273 0.938167 11.00000 0.08323 0.04430 = 0.05526 -0.00362 -0.00658 0.00135 AFIX 43 H11A 2 0.511219 0.661643 0.955337 11.00000 -1.20000 AFIX 0 C12 1 0.356133 0.565103 0.977566 11.00000 0.09015 0.08190 = 0.04119 -0.00533 0.00164 0.02518 AFIX 43 H12A 2 0.353534 0.648462 1.021543 11.00000 -1.20000 AFIX 0 C13 1 0.268663 0.439225 0.953250 11.00000 0.06222 0.10036 = 0.06749 0.01275 0.01259 0.01716 AFIX 43 H13A 2 0.205065 0.436490 0.979603 11.00000 -1.20000 AFIX 0 C14 1 0.272967 0.313688 0.889118 11.00000 0.05585 0.05641 = 0.06051 0.00600 0.00475 0.00371 AFIX 43 H14A 2 0.212198 0.225228 0.873464 11.00000 -1.20000 AFIX 0 C15 1 0.516126 -0.029706 0.647011 11.00000 0.11250 0.06564 = 0.09224 -0.01817 0.01770 0.01651 AFIX 137 H15A 2 0.461612 -0.123241 0.659435 11.00000 -1.50000 H15B 2 0.590883 -0.089738 0.647689 11.00000 -1.50000 H15C 2 0.485549 0.024023 0.592559 11.00000 -1.50000 AFIX 0 O21 4 1.090031 0.938596 0.754346 11.00000 0.06370 0.05173 = 0.05678 -0.00105 -0.00374 -0.01148 C22 1 1.132422 0.760419 0.791556 11.00000 0.05203 0.06852 = 0.07205 0.01717 -0.00889 -0.00566 AFIX 23 H22A 2 1.138867 0.764236 0.851736 11.00000 -1.20000 H22B 2 1.209441 0.730858 0.780470 11.00000 -1.20000 AFIX 0 C23 1 1.040534 0.610408 0.750765 11.00000 0.03528 0.05158 = 0.06308 0.00556 0.00827 -0.00339 AFIX 13 H23A 2 1.080003 0.492317 0.739341 11.00000 -1.20000 AFIX 0 N24 3 0.988374 0.707806 0.672497 11.00000 0.04343 0.03692 = 0.05263 0.00024 -0.00446 0.00220 C25 1 0.894220 0.640247 0.618759 11.00000 0.04794 0.05006 = 0.05419 -0.00434 0.00679 0.00727 O25 4 0.856174 0.477122 0.625288 11.00000 0.05321 0.04175 = 0.09045 -0.00464 0.00294 -0.01236 C26 1 0.829566 0.774164 0.553556 11.00000 0.10174 0.05794 = 0.07039 0.00630 -0.02674 -0.01619 AFIX 23 H26A 2 0.835336 0.723127 0.499347 11.00000 -1.20000 H26B 2 0.746727 0.769815 0.556130 11.00000 -1.20000 AFIX 0 C27 1 0.864459 0.977676 0.555283 11.00000 0.08096 0.06193 = 0.06659 0.01216 0.02135 0.01116 AFIX 13 H27A 2 0.793292 1.057635 0.545910 11.00000 -1.20000 AFIX 0 O27 4 0.918591 0.995215 0.485567 11.00000 0.17233 0.16982 = 0.11274 0.03382 -0.03280 -0.09236 AFIX 147 H27 2 0.880137 0.935075 0.445783 11.00000 -1.50000 AFIX 0 C28 1 0.947243 1.042044 0.632952 11.00000 0.06720 0.04572 = 0.07018 -0.01610 -0.00556 0.01413 AFIX 23 H28A 2 0.902353 1.069653 0.675303 11.00000 -1.20000 H28B 2 0.984742 1.160113 0.621210 11.00000 -1.20000 AFIX 0 C28A 1 1.042319 0.896980 0.667858 11.00000 0.05070 0.04036 = 0.04786 0.00123 0.00079 -0.00241 C29 1 0.950640 0.567503 0.803849 11.00000 0.05590 0.05857 = 0.05539 0.00021 -0.00380 -0.01076 C30 1 0.871918 0.703938 0.817251 11.00000 0.09719 0.06497 = 0.08793 -0.00336 0.02964 -0.00170 AFIX 43 H30A 2 0.869760 0.821275 0.790015 11.00000 -1.20000 AFIX 0 C31 1 0.793667 0.671135 0.871498 11.00000 0.09388 0.13379 = 0.09083 -0.02072 0.04339 -0.00596 AFIX 43 H31A 2 0.740181 0.765189 0.879249 11.00000 -1.20000 AFIX 0 C32 1 0.797629 0.501443 0.911896 11.00000 0.09359 0.15787 = 0.08974 0.01683 0.02525 -0.03327 AFIX 43 H32A 2 0.748007 0.479557 0.948743 11.00000 -1.20000 AFIX 0 C33 1 0.875750 0.359589 0.898459 11.00000 0.06933 0.13516 = 0.10364 0.06041 0.00238 -0.03991 AFIX 43 H33A 2 0.878164 0.242626 0.926019 11.00000 -1.20000 AFIX 0 C34 1 0.950992 0.393597 0.843117 11.00000 0.05646 0.08632 = 0.09873 0.02737 0.00356 -0.01644 AFIX 43 H34A 2 1.001587 0.297298 0.832965 11.00000 -1.20000 AFIX 0 C35 1 1.142032 0.888431 0.620033 11.00000 0.04859 0.05858 = 0.06880 0.01448 0.00773 -0.00159 AFIX 137 H35A 2 1.195496 0.786799 0.642194 11.00000 -1.50000 H35B 2 1.183894 1.008032 0.626139 11.00000 -1.50000 H35C 2 1.109332 0.865092 0.561731 11.00000 -1.50000 AFIX 0 HKLF 4 REM enr194_2_a.res in P2(1) REM wR2 = 0.1198, GooF = S = 0.713, Restrained GooF = 0.713 for all data REM R1 = 0.0507 for 1684 Fo > 4sig(Fo) and 0.1941 for all 5371 data REM 329 parameters refined using 1 restraints END WGHT 0.0403 0.0000 REM Highest difference peak 0.288, deepest hole -0.272, 1-sigma level 0.037 Q1 1 0.7461 0.9561 0.5966 11.00000 0.05 0.29 Q2 1 0.7867 1.1045 0.5236 11.00000 0.05 0.23 Q3 1 0.6079 0.5495 0.5773 11.00000 0.05 0.22 Q4 1 0.7760 0.6977 0.5183 11.00000 0.05 0.14 Q5 1 0.8735 0.9674 0.5383 11.00000 0.05 0.13 Q6 1 0.6729 0.7460 0.8449 11.00000 0.05 0.12 Q7 1 0.6479 0.7041 0.5974 11.00000 0.05 0.12 Q8 1 1.3466 0.6762 0.8425 11.00000 0.05 0.12 Q9 1 0.3441 0.7264 0.5755 11.00000 0.05 0.11 Q10 1 0.9563 1.0327 0.5879 11.00000 0.05 0.11 Q11 1 1.1642 0.7246 0.6114 11.00000 0.05 0.11 Q12 1 0.7349 0.6188 0.5776 11.00000 0.05 0.11 Q13 1 1.2349 1.0749 0.6087 11.00000 0.05 0.11 Q14 1 1.0020 1.3871 0.6277 11.00000 0.05 0.11 Q15 1 1.1546 1.1633 0.6350 11.00000 0.05 0.11 Q16 1 0.6427 0.4810 0.6974 11.00000 0.05 0.10 Q17 1 1.2237 0.5120 0.7844 11.00000 0.05 0.10 Q18 1 0.2271 0.0711 0.7097 11.00000 0.05 0.10 Q19 1 0.7579 0.0357 0.7017 11.00000 0.05 0.10 Q20 1 1.0158 0.7007 0.5646 11.00000 0.05 0.10 Q21 1 0.3488 -0.1336 0.7296 11.00000 0.05 0.10 Q22 1 0.9098 0.1877 0.8906 11.00000 0.05 0.10 Q23 1 0.9218 0.8875 0.7960 11.00000 0.05 0.10 Q24 1 1.2834 0.9321 0.8848 11.00000 0.05 0.10 Q25 1 0.6648 0.3828 0.4725 11.00000 0.05 0.10 Q26 1 0.3578 0.0367 0.9270 11.00000 0.05 0.10 Q27 1 0.2242 0.4249 0.6521 11.00000 0.05 0.10 Q28 1 0.4840 0.1701 0.5106 11.00000 0.05 0.10 Q29 1 0.5333 -0.1990 0.7095 11.00000 0.05 0.10 Q30 1 0.7652 0.4128 1.0544 11.00000 0.05 0.10 Q31 1 1.1920 0.8888 0.5566 11.00000 0.05 0.10 Q32 1 0.8102 0.1540 0.7834 11.00000 0.05 0.10 Q33 1 1.0615 0.9441 0.4815 11.00000 0.05 0.10 Q34 1 1.1088 0.9530 0.6292 11.00000 0.05 0.09 Q35 1 1.0974 0.8054 0.8454 11.00000 0.05 0.09 Q36 1 0.7678 1.0218 0.8179 11.00000 0.05 0.09 Q37 1 0.6436 0.5945 0.7678 11.00000 0.05 0.09 Q38 1 0.1872 0.2782 0.7168 11.00000 0.05 0.09 Q39 1 1.0182 0.6819 0.7076 11.00000 0.05 0.09 Q40 1 0.4965 0.6153 0.5113 11.00000 0.05 0.09 ; _shelx_res_checksum 21666 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_38 _database_code_depnum_ccdc_archive 'CCDC 2125371' loop_ _audit_author_name _audit_author_address 'Sylvain Bernes' ;Instituto de Fisica, BUAP, Puebla Mexico ; _audit_update_record ; 2021-11-30 deposited with the CCDC. 2022-01-21 downloaded from the CCDC. ; # Clave Lab. : ENR500 # Clave IF-UAP: ENR500 # Solicitud: 482 # Firma en la Solicitud: La solicitud no fue firmada # Clave datos : ... \BUAP\Sylvain\ENR500\50mm_1\ _database_code_CAS ? _database_code_CSD ? _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _audit_creation_date 2021-10-14 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point 369 _chemical_formula_moiety 'C7 H14 N O3, Cl, H2 O' _chemical_formula_sum 'C7 H16 Cl N O4' _chemical_formula_weight 213.66 _chemical_absolute_configuration ad _chemical_optical_rotation ? _chemical_properties_physical ? _chemical_properties_biological ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0013 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1009 0.0992 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0058 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _shelx_space_group_comment ? loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.2312(5) _cell_length_b 9.1140(9) _cell_length_c 13.9693(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1047.97(14) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 17116 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 23.84 _exptl_crystal_recrystallization_method ; Re-crystallisation from solvent: Methanol/AcOEt ; _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_F_000 456 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.442 _exptl_crystal_size_mid 0.093 _exptl_crystal_size_min 0.046 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 5 3 -2 0.0110 -5 -3 2 0.0350 -3 2 6 0.2030 3 -2 -6 0.2390 -2 -9 3 0.0420 1 7 -2 0.0510 _exptl_absorpt_coefficient_mu 0.185 _shelx_estimated_absorpt_T_min 0.923 _shelx_estimated_absorpt_T_max 0.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2094 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'X-AREA 1.88 (Stoe & Cie, 2019)' _diffrn_ambient_temperature 295(1) _diffrn_ambient_environment air _diffrn_measurement_specimen_support Mitegen _diffrn_source 'Sealed X-ray tube' _diffrn_source_type 'Axo Astix-f Microfocus source' _diffrn_source_voltage 65 _diffrn_source_current 0.600 _diffrn_source_power 0.039 _diffrn_radiation_collimation '0.6 mm diameter' _diffrn_radiation_probe x-ray _diffrn_radiation_type AgK\a _diffrn_radiation_wavelength 0.56083 _diffrn_radiation_monochromator 'Graded multilayer mirror' _diffrn_radiation_polarisn_norm -90 _diffrn_measurement_device 'Eulerian four-circle diffractometer' _diffrn_measurement_device_type 'Stoe Stadivari' _diffrn_detector 'Reverse-biased silicon diode array' _diffrn_detector_type 'Dectris Pilatus 100K R' _diffrn_measurement_method '\w scans' _diffrn_measurement_details ; 1545 frames, 100-140 s/frame, 1 deg./frame, detector distance = 50 mm ; _diffrn_detector_area_resol_mean 5.81 _diffrn_reflns_number 29183 _diffrn_reflns_av_unetI/netI 0.0403 _diffrn_reflns_av_R_equivalents 0.0792 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.105 _diffrn_reflns_theta_max 20.990 _diffrn_reflns_theta_full 19.664 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_point_group_measured_fraction_full 0.990 _reflns_number_total 2273 _reflns_number_gt 1768 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.713 _reflns_Friedel_fraction_max 0.994 _reflns_Friedel_fraction_full 0.992 _reflns_special_details ? _computing_data_collection 'X-AREA 1.88 (Stoe & Cie, 2019)' _computing_cell_refinement 'X-AREA 1.88' _computing_data_reduction 'X-AREA 1.88' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015a)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)' _computing_publication_material 'PublCif (Westrip, 2010)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0247P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 625 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.06(5) _refine_ls_number_reflns 2273 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0531 _refine_ls_wR_factor_gt 0.0501 _refine_ls_goodness_of_fit_ref 0.877 _refine_ls_restrained_S_all 0.877 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.38116(6) -0.00930(7) 0.42282(4) 0.04655(17) Uani 1 1 d . . . . . N1 N 0.2581(2) 0.3204(2) 0.37246(14) 0.0357(4) Uani 1 1 d . . . . . H1A H 0.139(3) 0.307(3) 0.3712(18) 0.054 Uiso 1 1 d . U . . . H1B H 0.300(3) 0.231(3) 0.3885(19) 0.054 Uiso 1 1 d . U . . . C2 C 0.3004(2) 0.4344(2) 0.44583(16) 0.0349(5) Uani 1 1 d . . . . . H2A H 0.244253 0.408829 0.505395 0.042 Uiso 1 1 calc R U . . . C3 C 0.2394(3) 0.5844(2) 0.41395(17) 0.0364(5) Uani 1 1 d . . . . . H3A H 0.121544 0.584797 0.414305 0.044 Uiso 1 1 calc R U . . . H3B H 0.276490 0.658430 0.458795 0.044 Uiso 1 1 calc R U . . . C4 C 0.2998(3) 0.6221(3) 0.31433(18) 0.0409(6) Uani 1 1 d . . . . . H4 H 0.418753 0.627142 0.315109 0.049 Uiso 1 1 calc R U . . . C5 C 0.2469(3) 0.5065(3) 0.24332(15) 0.0432(5) Uani 1 1 d . . . . . H5A H 0.288429 0.531594 0.180425 0.052 Uiso 1 1 calc R U . . . H5B H 0.129263 0.505389 0.239740 0.052 Uiso 1 1 calc R U . . . C6 C 0.3070(3) 0.3547(3) 0.27073(17) 0.0405(6) Uani 1 1 d . . . . . H6 H 0.425862 0.353965 0.266799 0.049 Uiso 1 1 calc R U . . . C7 C 0.4820(3) 0.4293(3) 0.46516(17) 0.0395(6) Uani 1 1 d . . . . . C8 C 0.2409(3) 0.2345(3) 0.2056(2) 0.0575(7) Uani 1 1 d . . . . . H8A H 0.273358 0.140388 0.229729 0.086 Uiso 1 1 calc R U . . . H8B H 0.283279 0.247500 0.142116 0.086 Uiso 1 1 calc R U . . . H8C H 0.124476 0.240072 0.203879 0.086 Uiso 1 1 calc R U . . . O1 O 0.57299(17) 0.3399(2) 0.43163(13) 0.0539(5) Uani 1 1 d . . . . . O2 O 0.5243(2) 0.5342(2) 0.52569(14) 0.0589(5) Uani 1 1 d . . . . . H2 H 0.627(4) 0.523(4) 0.537(2) 0.088 Uiso 1 1 d . U . . . O3 O 0.2363(2) 0.7597(2) 0.28354(13) 0.0559(5) Uani 1 1 d . . . . . H3 H 0.278(4) 0.832(4) 0.317(2) 0.084 Uiso 1 1 d . U . . . O4 O -0.07173(19) 0.3146(3) 0.38125(16) 0.0619(6) Uani 1 1 d . . . . . H4A H -0.118(4) 0.380(4) 0.415(3) 0.093 Uiso 1 1 d . U . . . H4B H -0.131(4) 0.306(4) 0.333(3) 0.093 Uiso 1 1 d . U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0417(2) 0.0425(3) 0.0554(4) -0.0082(3) 0.0033(3) 0.0037(3) N1 0.0311(9) 0.0360(11) 0.0402(12) -0.0028(10) -0.0007(9) -0.0001(9) C2 0.0344(10) 0.0391(12) 0.0313(13) -0.0017(10) 0.0000(9) 0.0004(10) C3 0.0366(10) 0.0379(12) 0.0348(12) -0.0040(11) -0.0006(11) 0.0025(10) C4 0.0406(12) 0.0407(14) 0.0413(14) 0.0025(12) -0.0035(11) -0.0014(11) C5 0.0476(10) 0.0498(13) 0.0322(12) 0.0004(13) -0.0016(10) 0.0019(14) C6 0.0368(11) 0.0475(14) 0.0373(14) -0.0041(12) 0.0005(10) 0.0022(11) C7 0.0393(11) 0.0422(14) 0.0370(13) 0.0020(12) -0.0059(10) -0.0009(11) C8 0.0621(16) 0.0589(17) 0.0514(17) -0.0184(14) -0.0089(14) 0.0069(15) O1 0.0372(8) 0.0619(11) 0.0625(12) -0.0165(10) -0.0062(9) 0.0067(8) O2 0.0472(9) 0.0586(13) 0.0711(12) -0.0222(10) -0.0201(9) 0.0058(9) O3 0.0800(13) 0.0396(10) 0.0480(11) 0.0052(9) -0.0161(10) -0.0009(10) O4 0.0381(10) 0.0905(16) 0.0571(14) -0.0232(12) 0.0001(8) -0.0005(9) _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.500(3) . ? N1 C6 1.510(3) . ? N1 H1A 0.99(3) . ? N1 H1B 0.91(3) . ? C2 C7 1.519(3) . ? C2 C3 1.523(3) . ? C2 H2A 0.9800 . ? C3 C4 1.517(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O3 1.425(3) . ? C4 C5 1.511(3) . ? C4 H4 0.9800 . ? C5 C6 1.518(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C8 1.524(3) . ? C6 H6 0.9800 . ? C7 O1 1.202(3) . ? C7 O2 1.323(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? O2 H2 0.87(3) . ? O3 H3 0.87(3) . ? O4 H4A 0.85(4) . ? O4 H4B 0.83(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 115.95(18) . . ? C2 N1 H1A 109.1(14) . . ? C6 N1 H1A 105.9(15) . . ? C2 N1 H1B 111.3(17) . . ? C6 N1 H1B 108.4(17) . . ? H1A N1 H1B 106(2) . . ? N1 C2 C7 109.20(19) . . ? N1 C2 C3 110.18(17) . . ? C7 C2 C3 113.82(19) . . ? N1 C2 H2A 107.8 . . ? C7 C2 H2A 107.8 . . ? C3 C2 H2A 107.8 . . ? C4 C3 C2 111.29(18) . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? O3 C4 C5 108.0(2) . . ? O3 C4 C3 110.8(2) . . ? C5 C4 C3 110.5(2) . . ? O3 C4 H4 109.1 . . ? C5 C4 H4 109.1 . . ? C3 C4 H4 109.1 . . ? C4 C5 C6 112.07(18) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? N1 C6 C5 109.83(19) . . ? N1 C6 C8 108.5(2) . . ? C5 C6 C8 112.8(2) . . ? N1 C6 H6 108.5 . . ? C5 C6 H6 108.5 . . ? C8 C6 H6 108.5 . . ? O1 C7 O2 125.1(2) . . ? O1 C7 C2 124.4(2) . . ? O2 C7 C2 110.5(2) . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 O2 H2 107(2) . . ? C4 O3 H3 111(2) . . ? H4A O4 H4B 105(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C7 -74.1(2) . . . . ? C6 N1 C2 C3 51.6(2) . . . . ? N1 C2 C3 C4 -53.6(2) . . . . ? C7 C2 C3 C4 69.4(2) . . . . ? C2 C3 C4 O3 177.48(18) . . . . ? C2 C3 C4 C5 57.7(2) . . . . ? O3 C4 C5 C6 -179.22(19) . . . . ? C3 C4 C5 C6 -57.8(2) . . . . ? C2 N1 C6 C5 -51.1(2) . . . . ? C2 N1 C6 C8 -174.87(19) . . . . ? C4 C5 C6 N1 53.0(2) . . . . ? C4 C5 C6 C8 174.3(2) . . . . ? N1 C2 C7 O1 -5.1(3) . . . . ? C3 C2 C7 O1 -128.7(3) . . . . ? N1 C2 C7 O2 176.50(19) . . . . ? C3 C2 C7 O2 52.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O4 H4A Cl1 0.85(4) 2.55(4) 3.285(2) 145(3) 4_456 yes O4 H4A O1 0.85(4) 2.58(3) 3.017(2) 113(3) 1_455 yes N1 H1A O4 0.99(3) 1.74(3) 2.718(3) 169(2) . yes N1 H1B Cl1 0.91(3) 2.34(3) 3.249(2) 174(2) . yes O2 H2 Cl1 0.87(3) 2.17(3) 3.0326(18) 175(3) 4_556 yes O3 H3 Cl1 0.87(3) 2.24(4) 3.105(2) 170(3) 1_565 yes O4 H4B O3 0.83(4) 1.90(4) 2.718(3) 169(3) 3_545 yes _refine_diff_density_max 0.178 _refine_diff_density_min -0.103 _refine_diff_density_rms 0.029 _shelx_res_file ; TITL enr500_a.res in P2(1)2(1)2(1) ENR500.res created by SHELXL-2018/3 at 21:10:08 on 13-Oct-2021 CELL 0.56083 8.2312 9.1140 13.9693 90.000 90.000 90.000 ZERR 4.00 0.0005 0.0009 0.0010 0.000 0.000 0.000 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H Cl N O DISP C 0.0013 0.0009 7.4 DISP Cl 0.1009 0.0992 336.8 DISP H 0 0 0.7 DISP N 0.003 0.002 11.7 DISP O 0.0058 0.0036 18.2 UNIT 28 64 4 4 16 TEMP 22 SIZE 0.442 0.093 0.046 L.S. 12 PLAN 2 CONF LIST 4 BOND $H FMAP 2 EQIV $1 x-1/2, -y+1/2, -z+1 EQIV $2 x-1, y, z EQIV $3 x+1/2, -y+1/2, -z+1 EQIV $4 x, y+1, z EQIV $5 -x, y-1/2, -z+1/2 HTAB O4 Cl1_$1 HTAB O4 O1_$2 HTAB N1 O4 HTAB N1 Cl1 HTAB O2 Cl1_$3 HTAB O3 Cl1_$4 HTAB O4 O3_$5 ACTA WGHT 0.024700 FVAR 0.91377 CL1 3 0.381156 -0.009298 0.422818 11.00000 0.04171 0.04254 = 0.05539 -0.00821 0.00328 0.00365 N1 4 0.258054 0.320437 0.372463 11.00000 0.03106 0.03597 = 0.04018 -0.00278 -0.00075 -0.00006 H1A 2 0.138803 0.307143 0.371225 11.00000 -1.50000 H1B 2 0.299760 0.231188 0.388474 11.00000 -1.50000 C2 1 0.300427 0.434380 0.445829 11.00000 0.03440 0.03906 = 0.03132 -0.00171 -0.00003 0.00040 AFIX 13 H2A 2 0.244253 0.408829 0.505395 11.00000 -1.20000 AFIX 0 C3 1 0.239386 0.584400 0.413953 11.00000 0.03661 0.03788 = 0.03477 -0.00401 -0.00061 0.00253 AFIX 23 H3A 2 0.121544 0.584797 0.414305 11.00000 -1.20000 H3B 2 0.276490 0.658430 0.458795 11.00000 -1.20000 AFIX 0 C4 1 0.299834 0.622062 0.314329 11.00000 0.04059 0.04070 = 0.04134 0.00245 -0.00353 -0.00145 AFIX 13 H4 2 0.418753 0.627142 0.315109 11.00000 -1.20000 AFIX 0 C5 1 0.246944 0.506490 0.243320 11.00000 0.04758 0.04981 = 0.03223 0.00041 -0.00157 0.00190 AFIX 23 H5A 2 0.288429 0.531594 0.180425 11.00000 -1.20000 H5B 2 0.129263 0.505389 0.239740 11.00000 -1.20000 AFIX 0 C6 1 0.306993 0.354743 0.270729 11.00000 0.03680 0.04746 = 0.03730 -0.00410 0.00052 0.00221 AFIX 13 H6 2 0.425862 0.353965 0.266799 11.00000 -1.20000 AFIX 0 C7 1 0.482002 0.429277 0.465163 11.00000 0.03934 0.04224 = 0.03701 0.00198 -0.00585 -0.00089 C8 1 0.240909 0.234549 0.205582 11.00000 0.06206 0.05894 = 0.05141 -0.01835 -0.00894 0.00689 AFIX 137 H8A 2 0.273358 0.140388 0.229729 11.00000 -1.50000 H8B 2 0.283279 0.247500 0.142116 11.00000 -1.50000 H8C 2 0.124476 0.240072 0.203879 11.00000 -1.50000 AFIX 0 O1 5 0.572989 0.339858 0.431633 11.00000 0.03721 0.06191 = 0.06251 -0.01654 -0.00624 0.00671 O2 5 0.524312 0.534201 0.525687 11.00000 0.04718 0.05860 = 0.07106 -0.02222 -0.02007 0.00583 H2 2 0.626930 0.523315 0.537064 11.00000 -1.50000 O3 5 0.236338 0.759690 0.283542 11.00000 0.07996 0.03961 = 0.04802 0.00523 -0.01608 -0.00090 H3 2 0.277721 0.832196 0.316543 11.00000 -1.50000 O4 5 -0.071728 0.314616 0.381250 11.00000 0.03808 0.09047 = 0.05711 -0.02324 0.00011 -0.00048 H4A 2 -0.117521 0.379616 0.415280 11.00000 -1.50000 H4B 2 -0.130820 0.305521 0.333329 11.00000 -1.50000 HKLF 4 REM enr500_a.res in P2(1)2(1)2(1) REM wR2 = 0.0531, GooF = S = 0.877, Restrained GooF = 0.877 for all data REM R1 = 0.0271 for 1768 Fo > 4sig(Fo) and 0.0424 for all 2273 data REM 137 parameters refined using 0 restraints END WGHT 0.0247 0.0000 REM Highest difference peak 0.178, deepest hole -0.103, 1-sigma level 0.029 Q1 1 0.3060 -0.0004 0.3806 11.00000 0.05 0.18 Q2 1 0.3850 0.4598 0.4465 11.00000 0.05 0.13 ; _shelx_res_checksum 89466 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_33a _database_code_depnum_ccdc_archive 'CCDC 2125370' loop_ _audit_author_name _audit_author_address 'Sylvain Bernes' ;Instituto de Fisica, BUAP, Puebla Mexico ; _audit_update_record ; 2021-11-30 deposited with the CCDC. 2022-01-21 downloaded from the CCDC. ; # Clave Lab. : ENR-356-1 # Clave IF-UAP: ENR_356_1 # Solicitud: 336 # Firma en la Solicitud: Dr. David Aparicio (ICUAP) # Clave datos : ... \BUAP\Sylvain\ENR_356_1\40mm_1\ _database_code_CAS ? _database_code_CSD ? _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _audit_creation_date 2019-06-07 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H21 N O2' _chemical_formula_sum 'C14 H21 N O2' _chemical_formula_weight 235.32 _chemical_absolute_configuration syn _chemical_optical_rotation ? _chemical_properties_physical ? _chemical_properties_biological ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _shelx_space_group_comment ? loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.0341(8) _cell_length_b 14.022(2) _cell_length_c 14.321(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1412.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 6607 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 21.51 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.107 _exptl_crystal_F_000 512 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.441 _exptl_crystal_size_mid 0.063 _exptl_crystal_size_min 0.034 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 3 4 3 0.0220 -3 -5 -4 0.0120 0 -1 1 0.0310 0 6 -5 0.0320 -3 5 7 0.2220 1 -2 -2 0.2190 _exptl_absorpt_coefficient_mu 0.047 _shelx_estimated_absorpt_T_min 0.980 _shelx_estimated_absorpt_T_max 0.998 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1182 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'X-AREA 1.86 (Stoe & Cie, 2018)' _diffrn_ambient_temperature 295(1) _diffrn_ambient_environment air _diffrn_measurement_specimen_support Mitegen _diffrn_source 'Sealed X-ray tube' _diffrn_source_type 'Axo Astix-f Microfocus source' _diffrn_source_voltage 65 _diffrn_source_current 0.600 _diffrn_source_power 0.039 _diffrn_radiation_collimation '0.6 mm diameter' _diffrn_radiation_probe x-ray _diffrn_radiation_type AgK\a _diffrn_radiation_wavelength 0.56083 _diffrn_radiation_monochromator 'Graded multilayer mirror' _diffrn_radiation_polarisn_norm -90 _diffrn_measurement_device 'Eulerian four-circle diffractometer' _diffrn_measurement_device_type 'Stoe Stadivari' _diffrn_detector 'Reverse-biased silicon diode array' _diffrn_detector_type 'Dectris Pilatus 100K R' _diffrn_measurement_method '\w scans' _diffrn_measurement_details ; 1127 frames, 80 s/frame, 1 deg./frame, detector distance = 40 mm ; _diffrn_detector_area_resol_mean 5.81 _diffrn_reflns_number 30320 _diffrn_reflns_av_unetI/netI 0.1422 _diffrn_reflns_av_R_equivalents 0.1988 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.546 _diffrn_reflns_theta_max 20.499 _diffrn_reflns_theta_full 19.664 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 0.998 _reflns_number_total 2885 _reflns_number_gt 1087 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.724 _reflns_Friedel_fraction_max 1.000 _reflns_Friedel_fraction_full 1.000 _reflns_special_details ? _computing_data_collection 'X-AREA 1.86 (Stoe & Cie, 2018)' _computing_cell_refinement 'X-AREA 1.86' _computing_data_reduction 'X-AREA 1.86' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015a)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)' _computing_publication_material 'PublCif (Westrip, 2010)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0219P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? # -0.2(10) _refine_ls_number_reflns 2885 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1343 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0736 _refine_ls_wR_factor_gt 0.0593 _refine_ls_goodness_of_fit_ref 0.681 _refine_ls_restrained_S_all 0.681 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3673(3) 0.5729(2) 0.30187(19) 0.0403(8) Uani 1 1 d . . . . . C2 C 0.5080(5) 0.5088(2) 0.2574(3) 0.0468(10) Uani 1 1 d . . . . . H2A H 0.448490 0.476104 0.204391 0.056 Uiso 1 1 calc R U . . . C3 C 0.5683(4) 0.4348(3) 0.3305(3) 0.0510(10) Uani 1 1 d . . . . . H3A H 0.661123 0.391931 0.303260 0.061 Uiso 1 1 calc R U . . . H3B H 0.628012 0.467163 0.382716 0.061 Uiso 1 1 calc R U . . . C4 C 0.4016(5) 0.3781(3) 0.3653(3) 0.0529(11) Uani 1 1 d . . . . . H4A H 0.347773 0.341213 0.313499 0.064 Uiso 1 1 calc R U . . . O4 O 0.4573(4) 0.3138(2) 0.4391(2) 0.0733(10) Uani 1 1 d . . . . . H4 H 0.548(6) 0.288(3) 0.430(3) 0.110 Uiso 1 1 d . U . . . C5 C 0.2506(5) 0.4442(3) 0.4042(3) 0.0526(11) Uani 1 1 d . . . . . H5A H 0.297860 0.475351 0.460038 0.063 Uiso 1 1 calc R U . . . H5B H 0.138441 0.407693 0.420956 0.063 Uiso 1 1 calc R U . . . C6 C 0.1989(4) 0.5190(2) 0.3308(3) 0.0495(11) Uani 1 1 d . . . . . H6A H 0.143349 0.487814 0.276866 0.059 Uiso 1 1 calc R U . . . H6B H 0.105079 0.562489 0.356365 0.059 Uiso 1 1 calc R U . . . C7 C 0.3181(5) 0.6595(3) 0.2480(2) 0.0425(10) Uani 1 1 d . . . . . H7A H 0.439063 0.686651 0.226943 0.051 Uiso 1 1 calc R U . . . C8 C 0.2042(5) 0.6397(3) 0.1606(3) 0.0543(11) Uani 1 1 d . . . . . H8A H 0.257716 0.585684 0.127452 0.065 Uiso 1 1 calc R U . . . H8B H 0.073699 0.624675 0.176866 0.065 Uiso 1 1 calc R U . . . O8 O 0.2098(4) 0.7233(2) 0.10245(18) 0.0608(9) Uani 1 1 d . . . . . H8 H 0.171(7) 0.716(3) 0.061(3) 0.091 Uiso 1 1 d . U . . . C9 C 0.6831(4) 0.5630(3) 0.2235(3) 0.0773(15) Uani 1 1 d . . . . . H9A H 0.649501 0.601781 0.170753 0.116 Uiso 1 1 calc R U . . . H9B H 0.779997 0.518379 0.205490 0.116 Uiso 1 1 calc R U . . . H9C H 0.730032 0.602897 0.272818 0.116 Uiso 1 1 calc R U . . . C10 C 0.2313(5) 0.7325(3) 0.3132(3) 0.0484(10) Uani 1 1 d . . . . . C11 C 0.3436(6) 0.7665(3) 0.3846(3) 0.0745(14) Uani 1 1 d . . . . . H11A H 0.467702 0.744484 0.390511 0.089 Uiso 1 1 calc R U . . . C12 C 0.2737(10) 0.8340(4) 0.4486(4) 0.108(2) Uani 1 1 d . . . . . H12A H 0.350444 0.856992 0.496417 0.130 Uiso 1 1 calc R U . . . C13 C 0.0904(11) 0.8650(4) 0.4390(4) 0.113(2) Uani 1 1 d . . . . . H13A H 0.042007 0.909121 0.481301 0.135 Uiso 1 1 calc R U . . . C14 C -0.0208(7) 0.8329(4) 0.3696(4) 0.0916(17) Uani 1 1 d . . . . . H14A H -0.145052 0.854975 0.364357 0.110 Uiso 1 1 calc R U . . . C15 C 0.0479(6) 0.7671(3) 0.3056(3) 0.0666(12) Uani 1 1 d . . . . . H15A H -0.029836 0.746161 0.257203 0.080 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0398(16) 0.0374(19) 0.044(2) 0.0032(18) 0.0045(16) -0.0015(15) C2 0.0458(19) 0.045(3) 0.050(3) -0.002(2) 0.0074(19) -0.003(2) C3 0.050(2) 0.052(3) 0.050(3) -0.006(2) 0.008(2) 0.006(2) C4 0.069(3) 0.046(3) 0.044(3) 0.005(2) 0.005(2) 0.010(2) O4 0.088(2) 0.072(2) 0.060(2) 0.0234(17) 0.0293(19) 0.0317(19) C5 0.055(2) 0.051(3) 0.052(3) 0.006(2) 0.010(2) 0.004(2) C6 0.051(2) 0.047(3) 0.051(3) 0.006(2) 0.009(2) 0.004(2) C7 0.046(2) 0.046(3) 0.036(2) 0.001(2) -0.002(2) -0.0066(19) C8 0.065(2) 0.049(3) 0.049(3) 0.006(2) -0.005(2) -0.010(2) O8 0.078(2) 0.061(2) 0.043(2) 0.0098(18) -0.0115(16) -0.0169(16) C9 0.052(2) 0.074(3) 0.105(4) 0.019(3) 0.032(3) 0.002(2) C10 0.064(2) 0.042(2) 0.039(3) 0.008(2) -0.002(2) 0.000(2) C11 0.108(3) 0.060(3) 0.056(3) -0.009(3) -0.010(3) 0.015(3) C12 0.183(6) 0.082(4) 0.061(4) -0.014(3) -0.027(4) 0.014(5) C13 0.193(7) 0.068(4) 0.077(5) -0.004(4) 0.019(5) 0.046(5) C14 0.108(4) 0.082(4) 0.085(5) 0.017(3) 0.022(4) 0.032(4) C15 0.076(3) 0.058(3) 0.065(3) 0.003(3) 0.008(3) 0.007(3) _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.464(4) . ? N1 C7 1.479(4) . ? N1 C2 1.481(4) . ? C2 C9 1.527(4) . ? C2 C3 1.533(5) . ? C2 H2A 0.9800 . ? C3 C4 1.502(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O4 1.443(4) . ? C4 C5 1.516(4) . ? C4 H4A 0.9800 . ? O4 H4 0.75(4) . ? C5 C6 1.530(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.512(4) . ? C7 C10 1.515(5) . ? C7 H7A 0.9800 . ? C8 O8 1.438(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O8 H8 0.66(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.376(5) . ? C10 C15 1.383(4) . ? C11 C12 1.406(6) . ? C11 H11A 0.9300 . ? C12 C13 1.367(6) . ? C12 H12A 0.9300 . ? C13 C14 1.343(7) . ? C13 H13A 0.9300 . ? C14 C15 1.388(5) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C7 112.4(2) . . ? C6 N1 C2 110.4(3) . . ? C7 N1 C2 115.5(3) . . ? N1 C2 C9 111.9(3) . . ? N1 C2 C3 107.5(3) . . ? C9 C2 C3 109.3(3) . . ? N1 C2 H2A 109.3 . . ? C9 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C4 C3 C2 111.7(3) . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? O4 C4 C3 111.2(3) . . ? O4 C4 C5 107.6(3) . . ? C3 C4 C5 110.2(3) . . ? O4 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? C4 O4 H4 114(4) . . ? C4 C5 C6 109.5(3) . . ? C4 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? C4 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? N1 C6 C5 110.9(3) . . ? N1 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N1 C7 C8 113.9(3) . . ? N1 C7 C10 109.1(3) . . ? C8 C7 C10 114.9(3) . . ? N1 C7 H7A 106.1 . . ? C8 C7 H7A 106.1 . . ? C10 C7 H7A 106.1 . . ? O8 C8 C7 108.4(3) . . ? O8 C8 H8A 110.0 . . ? C7 C8 H8A 110.0 . . ? O8 C8 H8B 110.0 . . ? C7 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? C8 O8 H8 113(4) . . ? C2 C9 H9A 109.5 . . ? C2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 118.2(4) . . ? C11 C10 C7 117.4(3) . . ? C15 C10 C7 124.3(4) . . ? C10 C11 C12 121.1(5) . . ? C10 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C13 C12 C11 118.6(6) . . ? C13 C12 H12A 120.7 . . ? C11 C12 H12A 120.7 . . ? C14 C13 C12 121.1(6) . . ? C14 C13 H13A 119.4 . . ? C12 C13 H13A 119.4 . . ? C13 C14 C15 120.6(5) . . ? C13 C14 H14A 119.7 . . ? C15 C14 H14A 119.7 . . ? C10 C15 C14 120.4(4) . . ? C10 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C9 178.2(3) . . . . ? C7 N1 C2 C9 49.3(4) . . . . ? C6 N1 C2 C3 -61.7(4) . . . . ? C7 N1 C2 C3 169.3(3) . . . . ? N1 C2 C3 C4 59.2(4) . . . . ? C9 C2 C3 C4 -179.1(3) . . . . ? C2 C3 C4 O4 -175.6(3) . . . . ? C2 C3 C4 C5 -56.4(4) . . . . ? O4 C4 C5 C6 175.3(3) . . . . ? C3 C4 C5 C6 53.9(4) . . . . ? C7 N1 C6 C5 -166.9(3) . . . . ? C2 N1 C6 C5 62.5(4) . . . . ? C4 C5 C6 N1 -57.4(4) . . . . ? C6 N1 C7 C8 -58.3(4) . . . . ? C2 N1 C7 C8 69.6(4) . . . . ? C6 N1 C7 C10 71.5(4) . . . . ? C2 N1 C7 C10 -160.5(3) . . . . ? N1 C7 C8 O8 -164.6(3) . . . . ? C10 C7 C8 O8 68.5(4) . . . . ? N1 C7 C10 C11 62.4(4) . . . . ? C8 C7 C10 C11 -168.2(3) . . . . ? N1 C7 C10 C15 -117.7(4) . . . . ? C8 C7 C10 C15 11.6(5) . . . . ? C15 C10 C11 C12 0.6(6) . . . . ? C7 C10 C11 C12 -179.6(4) . . . . ? C10 C11 C12 C13 0.4(8) . . . . ? C11 C12 C13 C14 -0.7(9) . . . . ? C12 C13 C14 C15 0.0(9) . . . . ? C11 C10 C15 C14 -1.3(6) . . . . ? C7 C10 C15 C14 178.9(4) . . . . ? C13 C14 C15 C10 1.0(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O4 H4 O8 0.75(4) 1.98(4) 2.729(4) 176(5) 3_645 yes O8 H8 O4 0.66(4) 2.01(4) 2.669(4) 176(6) 2_564 yes _refine_diff_density_max 0.111 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.027 _shelx_res_file ; TITL enr_356_1_a.res in P2(1)2(1)2(1) ENR_356_1.res created by SHELXL-2018/3 at 19:07:23 on 07-Jun-2019 CELL 0.56083 7.0341 14.0215 14.3209 90.000 90.000 90.000 ZERR 4.00 0.0008 0.0020 0.0020 0.000 0.000 0.000 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 56 84 4 8 TEMP 22 SIZE 0.441 0.063 0.034 L.S. 10 PLAN 20 BOND $H CONF LIST 4 FMAP 2 EQIV $1 -x+1, y-1/2, -z+1/2 EQIV $2 -x+1/2, -y+1, z-1/2 HTAB O4 O8_$1 HTAB O8 O4_$2 ACTA WGHT 0.021900 FVAR 0.91299 N1 3 0.367293 0.572875 0.301874 11.00000 0.03979 0.03737 = 0.04387 0.00319 0.00447 -0.00145 C2 1 0.508011 0.508756 0.257364 11.00000 0.04584 0.04489 = 0.04954 -0.00226 0.00744 -0.00321 AFIX 13 H2A 2 0.448490 0.476104 0.204391 11.00000 -1.20000 AFIX 0 C3 1 0.568263 0.434833 0.330518 11.00000 0.05019 0.05245 = 0.05040 -0.00612 0.00840 0.00643 AFIX 23 H3A 2 0.661123 0.391931 0.303260 11.00000 -1.20000 H3B 2 0.628012 0.467163 0.382716 11.00000 -1.20000 AFIX 0 C4 1 0.401591 0.378057 0.365294 11.00000 0.06871 0.04642 = 0.04363 0.00480 0.00531 0.00970 AFIX 13 H4A 2 0.347773 0.341213 0.313499 11.00000 -1.20000 AFIX 0 O4 4 0.457258 0.313791 0.439086 11.00000 0.08750 0.07234 = 0.06017 0.02335 0.02929 0.03174 H4 2 0.548486 0.288052 0.429903 11.00000 -1.50000 C5 1 0.250570 0.444155 0.404223 11.00000 0.05485 0.05082 = 0.05217 0.00578 0.00969 0.00422 AFIX 23 H5A 2 0.297860 0.475351 0.460038 11.00000 -1.20000 H5B 2 0.138441 0.407693 0.420956 11.00000 -1.20000 AFIX 0 C6 1 0.198908 0.519035 0.330798 11.00000 0.05050 0.04670 = 0.05124 0.00584 0.00923 0.00370 AFIX 23 H6A 2 0.143349 0.487814 0.276866 11.00000 -1.20000 H6B 2 0.105079 0.562489 0.356365 11.00000 -1.20000 AFIX 0 C7 1 0.318092 0.659462 0.248007 11.00000 0.04589 0.04559 = 0.03607 0.00058 -0.00220 -0.00664 AFIX 13 H7A 2 0.439063 0.686651 0.226943 11.00000 -1.20000 AFIX 0 C8 1 0.204162 0.639707 0.160590 11.00000 0.06460 0.04949 = 0.04889 0.00580 -0.00471 -0.00975 AFIX 23 H8A 2 0.257716 0.585684 0.127452 11.00000 -1.20000 H8B 2 0.073699 0.624675 0.176866 11.00000 -1.20000 AFIX 0 O8 4 0.209798 0.723269 0.102446 11.00000 0.07845 0.06145 = 0.04251 0.00977 -0.01148 -0.01687 H8 2 0.171168 0.716301 0.061042 11.00000 -1.50000 C9 1 0.683141 0.562987 0.223459 11.00000 0.05211 0.07445 = 0.10522 0.01859 0.03193 0.00181 AFIX 137 H9A 2 0.649501 0.601781 0.170753 11.00000 -1.50000 H9B 2 0.779997 0.518379 0.205490 11.00000 -1.50000 H9C 2 0.730032 0.602897 0.272818 11.00000 -1.50000 AFIX 0 C10 1 0.231344 0.732505 0.313249 11.00000 0.06422 0.04241 = 0.03867 0.00838 -0.00150 -0.00007 C11 1 0.343573 0.766497 0.384558 11.00000 0.10757 0.06040 = 0.05564 -0.00904 -0.01049 0.01519 AFIX 43 H11A 2 0.467702 0.744484 0.390511 11.00000 -1.20000 AFIX 0 C12 1 0.273675 0.833977 0.448588 11.00000 0.18272 0.08156 = 0.06075 -0.01440 -0.02658 0.01412 AFIX 43 H12A 2 0.350444 0.856992 0.496417 11.00000 -1.20000 AFIX 0 C13 1 0.090423 0.865027 0.439019 11.00000 0.19263 0.06828 = 0.07711 -0.00372 0.01930 0.04584 AFIX 43 H13A 2 0.042007 0.909121 0.481301 11.00000 -1.20000 AFIX 0 C14 1 -0.020823 0.832910 0.369579 11.00000 0.10821 0.08177 = 0.08475 0.01707 0.02184 0.03247 AFIX 43 H14A 2 -0.145052 0.854975 0.364357 11.00000 -1.20000 AFIX 0 C15 1 0.047908 0.767110 0.305560 11.00000 0.07650 0.05779 = 0.06547 0.00324 0.00829 0.00694 AFIX 43 H15A 2 -0.029836 0.746161 0.257203 11.00000 -1.20000 AFIX 0 HKLF 4 REM enr_356_1_a.res in P2(1)2(1)2(1) REM wR2 = 0.0736, GooF = S = 0.681, Restrained GooF = 0.681 for all data REM R1 = 0.0372 for 1087 Fo > 4sig(Fo) and 0.1343 for all 2885 data REM 161 parameters refined using 0 restraints END WGHT 0.0228 0.0000 REM Highest difference peak 0.111, deepest hole -0.118, 1-sigma level 0.027 Q1 1 0.4308 0.5410 0.2814 11.00000 0.05 0.11 Q2 1 0.5941 0.5421 0.2338 11.00000 0.05 0.11 Q3 1 0.7807 0.4979 0.3486 11.00000 0.05 0.10 Q4 1 0.1269 0.4743 0.2192 11.00000 0.05 0.08 Q5 1 0.4510 0.4486 0.1408 11.00000 0.05 0.08 Q6 1 0.2867 0.5558 0.3138 11.00000 0.05 0.08 Q7 1 0.6684 0.6211 0.1975 11.00000 0.05 0.08 Q8 1 0.3433 0.6187 0.2834 11.00000 0.05 0.08 Q9 1 0.7496 0.3383 0.5190 11.00000 0.05 0.08 Q10 1 0.4373 0.9389 0.5237 11.00000 0.05 0.08 Q11 1 0.4335 0.3451 0.3977 11.00000 0.05 0.07 Q12 1 0.3712 0.3432 0.2007 11.00000 0.05 0.07 Q13 1 -0.2317 0.8562 0.3222 11.00000 0.05 0.07 Q14 1 0.2330 0.4785 0.3657 11.00000 0.05 0.07 Q15 1 0.7273 0.6432 0.3164 11.00000 0.05 0.07 Q16 1 0.5239 0.4694 0.2927 11.00000 0.05 0.07 Q17 1 0.0242 0.6237 0.3970 11.00000 0.05 0.07 Q18 1 0.6034 0.2124 0.4949 11.00000 0.05 0.07 Q19 1 0.1975 0.6775 0.1385 11.00000 0.05 0.07 Q20 1 0.1591 0.9581 0.5014 11.00000 0.05 0.07 ; _shelx_res_checksum 99551 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_29 _database_code_depnum_ccdc_archive 'CCDC 2125368' loop_ _audit_author_name _audit_author_address 'Sylvain Bernes' ;Instituto de Fisica, BUAP, Puebla Mexico ; _audit_update_record ; 2021-11-30 deposited with the CCDC. 2022-01-21 downloaded from the CCDC. ; # Clave Lab. : ENR157_1 # Clave IF-UAP: ENR157_1 # Solicitud: 124 # Firma en la Solicitud: Dr. Joel L. Teran (ICUAP) # Clave datos : ... \BUAP\Sylvain\ENR157_1\40mm_2\ _database_code_CAS ? _database_code_CSD ? _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _audit_creation_date 2018-06-25 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 N O3' _chemical_formula_sum 'C14 H15 N O3' _chemical_formula_weight 245.27 _chemical_absolute_configuration syn _chemical_optical_rotation ? _chemical_properties_physical ? _chemical_properties_biological ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _shelx_space_group_comment ? loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.4810(4) _cell_length_b 10.4640(9) _cell_length_c 15.9980(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1252.34(15) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 18729 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 24.84 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_F_000 520 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.150 _exptl_absorpt_coefficient_mu 0.057 _shelx_estimated_absorpt_T_min 0.972 _shelx_estimated_absorpt_T_max 0.991 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4137 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'X-AREA 1.82 (Stoe & Cie, 2018)' _diffrn_ambient_temperature 295(1) _diffrn_ambient_environment air _diffrn_measurement_specimen_support Mitegen _diffrn_source 'Sealed X-ray tube' _diffrn_source_type 'Axo Astix-f Microfocus source' _diffrn_source_voltage 65 _diffrn_source_current 0.600 _diffrn_source_power 0.039 _diffrn_radiation_collimation '0.6 mm diameter' _diffrn_radiation_probe x-ray _diffrn_radiation_type AgK\a _diffrn_radiation_wavelength 0.56083 _diffrn_radiation_monochromator 'Graded multilayer mirror' _diffrn_radiation_polarisn_norm -90 _diffrn_measurement_device 'Eulerian four-circle diffractometer' _diffrn_measurement_device_type 'Stoe Stadivari' _diffrn_detector 'Reverse-biased silicon diode array' _diffrn_detector_type 'Dectris Pilatus 100K R' _diffrn_measurement_method '\w scans' _diffrn_measurement_details ; 1400 frames, 20 s/frame, 1 deg./frame, detector distance = 40 mm ; _diffrn_detector_area_resol_mean 5.81 _diffrn_reflns_number 40682 _diffrn_reflns_av_unetI/netI 0.0471 _diffrn_reflns_av_R_equivalents 0.0823 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.372 _diffrn_reflns_theta_max 22.494 _diffrn_reflns_theta_full 19.664 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 3318 _reflns_number_gt 1955 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.734 _reflns_Friedel_fraction_max 1.000 _reflns_Friedel_fraction_full 1.000 _reflns_special_details ? _computing_data_collection 'X-AREA 1.82 (Stoe & Cie, 2018)' _computing_cell_refinement 'X-AREA 1.82' _computing_data_reduction 'X-AREA 1.82' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015a)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)' _computing_publication_material 'PublCif (Westrip, 2010)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0439P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_extinction_coef 0.020(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? # 0.7(9) _refine_ls_number_reflns 3318 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0762 _refine_ls_goodness_of_fit_ref 0.813 _refine_ls_restrained_S_all 0.813 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.08851(17) 0.57286(15) 0.25693(10) 0.0574(4) Uani 1 1 d . . . . . C2 C 0.2499(3) 0.5008(2) 0.24310(16) 0.0553(6) Uani 1 1 d . . . . . H2A H 0.264449 0.480864 0.184277 0.066 Uiso 1 1 calc R U . . . H2B H 0.248204 0.421696 0.274710 0.066 Uiso 1 1 calc R U . . . C3 C 0.4003(3) 0.5889(2) 0.27367(13) 0.0465(5) Uani 1 1 d . . . . . H3A H 0.492397 0.538326 0.302012 0.056 Uiso 1 1 calc R U . . . N4 N 0.30251(19) 0.66624(18) 0.33505(11) 0.0438(4) Uani 1 1 d . . . . . C5 C 0.3777(3) 0.7541(2) 0.38439(12) 0.0470(5) Uani 1 1 d . . . . . O2 O 0.53935(19) 0.77441(18) 0.38523(10) 0.0644(5) Uani 1 1 d . . . . . C6 C 0.2502(3) 0.8283(2) 0.43897(14) 0.0524(6) Uani 1 1 d . . . . . H6A H 0.299513 0.913040 0.447343 0.063 Uiso 1 1 calc R U . . . H6B H 0.245819 0.786941 0.493204 0.063 Uiso 1 1 calc R U . . . C7 C 0.0610(3) 0.8428(2) 0.40766(14) 0.0496(5) Uani 1 1 d . . . . . O3 O -0.0367(2) 0.92196(18) 0.43823(11) 0.0730(5) Uani 1 1 d . . . . . C8 C 0.0028(2) 0.7566(2) 0.33744(15) 0.0522(6) Uani 1 1 d . . . . . H8A H 0.017167 0.801141 0.284679 0.063 Uiso 1 1 calc R U . . . H8B H -0.122934 0.736369 0.344085 0.063 Uiso 1 1 calc R U . . . C8A C 0.1096(2) 0.6341(2) 0.33538(14) 0.0480(5) Uani 1 1 d . . . . . C9 C 0.4837(2) 0.6654(2) 0.20363(13) 0.0453(5) Uani 1 1 d . . . . . C10 C 0.3881(3) 0.7582(2) 0.16074(15) 0.0591(6) Uani 1 1 d . . . . . H10A H 0.273985 0.780545 0.178650 0.071 Uiso 1 1 calc R U . . . C11 C 0.4611(4) 0.8178(3) 0.09171(16) 0.0711(7) Uani 1 1 d . . . . . H11A H 0.396295 0.880390 0.063724 0.085 Uiso 1 1 calc R U . . . C12 C 0.6278(4) 0.7853(3) 0.06427(16) 0.0767(8) Uani 1 1 d . . . . . H12A H 0.675139 0.823484 0.016684 0.092 Uiso 1 1 calc R U . . . C13 C 0.7250(4) 0.6958(3) 0.10741(18) 0.0746(8) Uani 1 1 d . . . . . H13A H 0.839684 0.674878 0.089604 0.090 Uiso 1 1 calc R U . . . C14 C 0.6541(3) 0.6365(2) 0.17709(15) 0.0574(6) Uani 1 1 d . . . . . H14A H 0.721793 0.576709 0.206218 0.069 Uiso 1 1 calc R U . . . C15 C 0.0610(3) 0.5451(2) 0.40656(17) 0.0679(7) Uani 1 1 d . . . . . H15A H 0.128881 0.467565 0.401829 0.102 Uiso 1 1 calc R U . . . H15B H -0.064242 0.525618 0.404053 0.102 Uiso 1 1 calc R U . . . H15C H 0.087696 0.585740 0.458898 0.102 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0427(7) 0.0609(10) 0.0685(10) -0.0198(9) -0.0035(7) -0.0019(7) C2 0.0504(11) 0.0487(13) 0.0669(16) -0.0091(12) 0.0062(12) 0.0004(11) C3 0.0414(10) 0.0464(12) 0.0516(12) 0.0020(11) -0.0003(9) 0.0059(10) N4 0.0336(7) 0.0525(11) 0.0454(10) -0.0030(10) -0.0020(8) -0.0008(8) C5 0.0426(10) 0.0597(14) 0.0387(11) 0.0022(11) -0.0062(9) -0.0056(11) O2 0.0442(8) 0.0910(13) 0.0580(10) -0.0080(9) -0.0050(7) -0.0118(9) C6 0.0535(11) 0.0608(15) 0.0430(12) -0.0051(12) -0.0047(9) -0.0044(12) C7 0.0516(11) 0.0477(13) 0.0494(12) 0.0011(11) 0.0012(10) 0.0001(11) O3 0.0682(10) 0.0716(12) 0.0793(12) -0.0204(10) -0.0018(9) 0.0200(10) C8 0.0396(10) 0.0578(13) 0.0593(14) -0.0063(13) -0.0067(9) 0.0037(10) C8A 0.0374(9) 0.0500(13) 0.0565(13) -0.0060(12) 0.0008(10) -0.0019(9) C9 0.0457(10) 0.0467(12) 0.0435(11) -0.0074(10) -0.0008(9) -0.0042(10) C10 0.0603(12) 0.0657(15) 0.0514(13) 0.0012(14) -0.0010(12) 0.0016(13) C11 0.0922(18) 0.0731(18) 0.0480(14) 0.0045(14) -0.0091(14) -0.0059(17) C12 0.100(2) 0.085(2) 0.0458(14) -0.0019(15) 0.0113(15) -0.0268(19) C13 0.0683(15) 0.089(2) 0.0663(18) -0.0138(17) 0.0249(14) -0.0138(16) C14 0.0530(12) 0.0607(16) 0.0586(15) -0.0068(13) 0.0083(11) 0.0000(11) C15 0.0618(14) 0.0576(15) 0.0841(19) -0.0017(14) 0.0258(14) 0.0007(13) _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8A 1.418(3) . ? O1 C2 1.440(3) . ? C2 C3 1.535(3) . ? C3 N4 1.468(3) . ? C3 C9 1.512(3) . ? N4 C5 1.336(3) . ? N4 C8A 1.482(2) . ? C5 O2 1.228(2) . ? C5 C6 1.508(3) . ? C6 C7 1.509(3) . ? C7 O3 1.208(3) . ? C7 C8 1.505(3) . ? C8 C8A 1.511(3) . ? C8A C15 1.515(3) . ? C9 C14 1.377(3) . ? C9 C10 1.388(3) . ? C10 C11 1.381(3) . ? C11 C12 1.365(4) . ? C12 C13 1.372(4) . ? C13 C14 1.382(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8A O1 C2 106.21(15) . . ? O1 C2 C3 104.54(17) . . ? N4 C3 C9 114.19(18) . . ? N4 C3 C2 100.31(15) . . ? C9 C3 C2 112.60(18) . . ? C5 N4 C3 124.39(16) . . ? C5 N4 C8A 124.35(17) . . ? C3 N4 C8A 111.26(17) . . ? O2 C5 N4 122.7(2) . . ? O2 C5 C6 121.8(2) . . ? N4 C5 C6 115.46(16) . . ? C5 C6 C7 116.94(19) . . ? O3 C7 C8 122.6(2) . . ? O3 C7 C6 120.2(2) . . ? C8 C7 C6 117.29(19) . . ? C7 C8 C8A 111.82(17) . . ? O1 C8A N4 102.00(15) . . ? O1 C8A C8 110.11(18) . . ? N4 C8A C8 108.82(17) . . ? O1 C8A C15 111.14(18) . . ? N4 C8A C15 112.08(19) . . ? C8 C8A C15 112.22(18) . . ? C14 C9 C10 118.6(2) . . ? C14 C9 C3 119.6(2) . . ? C10 C9 C3 121.62(18) . . ? C11 C10 C9 120.5(2) . . ? C12 C11 C10 120.4(3) . . ? C11 C12 C13 119.5(3) . . ? C12 C13 C14 120.6(2) . . ? C9 C14 C13 120.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8A O1 C2 C3 -40.6(2) . . . . ? O1 C2 C3 N4 26.3(2) . . . . ? O1 C2 C3 C9 -95.5(2) . . . . ? C9 C3 N4 C5 -63.9(3) . . . . ? C2 C3 N4 C5 175.5(2) . . . . ? C9 C3 N4 C8A 116.26(19) . . . . ? C2 C3 N4 C8A -4.4(2) . . . . ? C3 N4 C5 O2 -3.2(4) . . . . ? C8A N4 C5 O2 176.6(2) . . . . ? C3 N4 C5 C6 176.26(19) . . . . ? C8A N4 C5 C6 -3.9(3) . . . . ? O2 C5 C6 C7 152.4(2) . . . . ? N4 C5 C6 C7 -27.2(3) . . . . ? C5 C6 C7 O3 -164.3(2) . . . . ? C5 C6 C7 C8 15.0(3) . . . . ? O3 C7 C8 C8A -155.2(2) . . . . ? C6 C7 C8 C8A 25.5(3) . . . . ? C2 O1 C8A N4 36.4(2) . . . . ? C2 O1 C8A C8 151.81(17) . . . . ? C2 O1 C8A C15 -83.2(2) . . . . ? C5 N4 C8A O1 160.98(19) . . . . ? C3 N4 C8A O1 -19.1(2) . . . . ? C5 N4 C8A C8 44.6(3) . . . . ? C3 N4 C8A C8 -135.48(18) . . . . ? C5 N4 C8A C15 -80.1(3) . . . . ? C3 N4 C8A C15 99.8(2) . . . . ? C7 C8 C8A O1 -163.52(17) . . . . ? C7 C8 C8A N4 -52.5(2) . . . . ? C7 C8 C8A C15 72.1(2) . . . . ? N4 C3 C9 C14 137.7(2) . . . . ? C2 C3 C9 C14 -108.8(2) . . . . ? N4 C3 C9 C10 -47.3(3) . . . . ? C2 C3 C9 C10 66.3(3) . . . . ? C14 C9 C10 C11 1.6(3) . . . . ? C3 C9 C10 C11 -173.5(2) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C10 C11 C12 C13 -2.1(4) . . . . ? C11 C12 C13 C14 1.5(4) . . . . ? C10 C9 C14 C13 -2.3(3) . . . . ? C3 C9 C14 C13 172.9(2) . . . . ? C12 C13 C14 C9 0.8(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C6 H6B O2 0.97 2.57 3.399(3) 144.1 4_466 yes C8 H8B O2 0.97 2.64 3.555(2) 157.2 1_455 yes _refine_diff_density_max 0.130 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.027 _shelx_res_file ; TITL enr157_1_a.res in P2(1)2(1)2(1) ENR157_1.res created by SHELXL-2018/3 at 11:14:56 on 25-Jun-2018 CELL 0.56083 7.4810 10.464 15.9980 90 90 90 ZERR 4 0.0004 0.0009 0.0010 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 56 60 4 12 TEMP 22 SIZE 0.50 0.30 0.15 L.S. 10 PLAN 20 CONF HTAB EQIV $1 x-1/2, -y+3/2, -z+1 EQIV $2 x-1, y, z HTAB C6 O2_$1 HTAB C8 O2_$2 LIST 4 FMAP 2 ACTA WGHT 0.043900 EXTI 0.020149 FVAR 1.02150 O1 4 0.088506 0.572860 0.256933 11.00000 0.04272 0.06091 = 0.06854 -0.01983 -0.00350 -0.00186 C2 1 0.249870 0.500791 0.243098 11.00000 0.05038 0.04866 = 0.06693 -0.00913 0.00619 0.00039 AFIX 23 H2A 2 0.264449 0.480864 0.184277 11.00000 -1.20000 H2B 2 0.248204 0.421696 0.274710 11.00000 -1.20000 AFIX 0 C3 1 0.400292 0.588896 0.273668 11.00000 0.04144 0.04640 = 0.05162 0.00198 -0.00033 0.00589 AFIX 13 H3A 2 0.492397 0.538326 0.302012 11.00000 -1.20000 AFIX 0 N4 3 0.302505 0.666243 0.335051 11.00000 0.03365 0.05249 = 0.04541 -0.00300 -0.00203 -0.00079 C5 1 0.377712 0.754116 0.384388 11.00000 0.04262 0.05970 = 0.03867 0.00222 -0.00624 -0.00563 O2 4 0.539352 0.774411 0.385232 11.00000 0.04423 0.09098 = 0.05802 -0.00803 -0.00504 -0.01184 C6 1 0.250216 0.828263 0.438968 11.00000 0.05348 0.06078 = 0.04302 -0.00512 -0.00472 -0.00436 AFIX 23 H6A 2 0.299513 0.913040 0.447343 11.00000 -1.20000 H6B 2 0.245819 0.786941 0.493204 11.00000 -1.20000 AFIX 0 C7 1 0.060990 0.842834 0.407663 11.00000 0.05163 0.04765 = 0.04938 0.00106 0.00118 0.00012 O3 4 -0.036688 0.921958 0.438232 11.00000 0.06818 0.07165 = 0.07932 -0.02040 -0.00177 0.01997 C8 1 0.002791 0.756636 0.337440 11.00000 0.03959 0.05779 = 0.05926 -0.00633 -0.00675 0.00375 AFIX 23 H8A 2 0.017167 0.801141 0.284679 11.00000 -1.20000 H8B 2 -0.122934 0.736369 0.344085 11.00000 -1.20000 AFIX 0 C8A 1 0.109635 0.634104 0.335383 11.00000 0.03741 0.05001 = 0.05651 -0.00601 0.00078 -0.00188 C9 1 0.483683 0.665357 0.203629 11.00000 0.04568 0.04667 = 0.04351 -0.00737 -0.00084 -0.00419 C10 1 0.388069 0.758245 0.160744 11.00000 0.06030 0.06568 = 0.05145 0.00120 -0.00100 0.00158 AFIX 43 H10A 2 0.273985 0.780545 0.178650 11.00000 -1.20000 AFIX 0 C11 1 0.461082 0.817761 0.091713 11.00000 0.09221 0.07311 = 0.04797 0.00452 -0.00912 -0.00592 AFIX 43 H11A 2 0.396295 0.880390 0.063724 11.00000 -1.20000 AFIX 0 C12 1 0.627826 0.785252 0.064271 11.00000 0.09955 0.08462 = 0.04579 -0.00187 0.01126 -0.02677 AFIX 43 H12A 2 0.675139 0.823484 0.016684 11.00000 -1.20000 AFIX 0 C13 1 0.725017 0.695797 0.107408 11.00000 0.06828 0.08936 = 0.06628 -0.01377 0.02487 -0.01377 AFIX 43 H13A 2 0.839684 0.674878 0.089604 11.00000 -1.20000 AFIX 0 C14 1 0.654084 0.636474 0.177085 11.00000 0.05304 0.06068 = 0.05861 -0.00683 0.00827 -0.00004 AFIX 43 H14A 2 0.721793 0.576709 0.206218 11.00000 -1.20000 AFIX 0 C15 1 0.061040 0.545103 0.406562 11.00000 0.06183 0.05765 = 0.08414 -0.00172 0.02577 0.00071 AFIX 137 H15A 2 0.128881 0.467565 0.401829 11.00000 -1.50000 H15B 2 -0.064242 0.525618 0.404053 11.00000 -1.50000 H15C 2 0.087696 0.585740 0.458898 11.00000 -1.50000 AFIX 0 HKLF 4 REM enr157_1_a.res in P2(1)2(1)2(1) REM wR2 = 0.0832, GooF = S = 0.813, Restrained GooF = 0.813 for all data REM R1 = 0.0379 for 1955 Fo > 4sig(Fo) and 0.0709 for all 3318 data REM 165 parameters refined using 0 restraints END WGHT 0.0438 0.0000 REM Instructions for potential hydrogen bonds HTAB C6 O2_$1 HTAB C8 O2_$2 REM Highest difference peak 0.130, deepest hole -0.163, 1-sigma level 0.027 Q1 1 0.2069 0.6580 0.3480 11.00000 0.05 0.13 Q2 1 -0.0348 0.5852 0.2352 11.00000 0.05 0.11 Q3 1 0.5888 0.6964 0.2057 11.00000 0.05 0.11 Q4 1 0.1444 0.8049 0.4352 11.00000 0.05 0.11 Q5 1 0.3037 0.7543 0.4326 11.00000 0.05 0.11 Q6 1 0.4604 0.8015 0.3526 11.00000 0.05 0.10 Q7 1 0.6133 0.7800 0.3383 11.00000 0.05 0.10 Q8 1 0.5038 0.7003 0.3857 11.00000 0.05 0.09 Q9 1 0.5394 0.6122 0.1666 11.00000 0.05 0.09 Q10 1 0.0388 0.9320 0.4028 11.00000 0.05 0.09 Q11 1 0.3211 0.7580 0.3358 11.00000 0.05 0.09 Q12 1 0.3041 0.8256 0.3924 11.00000 0.05 0.09 Q13 1 0.3149 0.5720 0.2342 11.00000 0.05 0.09 Q14 1 0.0001 0.5123 0.2744 11.00000 0.05 0.09 Q15 1 0.1686 0.8617 0.4017 11.00000 0.05 0.09 Q16 1 0.4208 0.6744 0.1587 11.00000 0.05 0.09 Q17 1 0.3477 0.6755 0.3733 11.00000 0.05 0.09 Q18 1 0.3745 0.5974 0.3371 11.00000 0.05 0.09 Q19 1 0.6125 0.7937 0.4263 11.00000 0.05 0.08 Q20 1 0.2538 0.5147 0.1854 11.00000 0.05 0.08 ; _shelx_res_checksum 65629