# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2021 ####################################################################### # # 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_AJGI_749_2_1 _database_code_depnum_ccdc_archive 'CCDC 2015200' loop_ _audit_author_name _audit_author_address 'Celine Besnard' ;university of Geneva Switzerland ; _audit_update_record ; 2020-07-09 deposited with the CCDC. 2020-11-23 downloaded from the CCDC. ; _audit_creation_date 2017-12-04 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _shelx_SHELXL_version_number 2017/1 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C31 H30 N4 O5 S' _chemical_formula_sum 'C31 H30 N4 O5 S' _chemical_formula_weight 570.65 _chemical_melting_point ? _chemical_oxdiff_formula 'C31 H30 N4 O5 S1' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.14023(8) _cell_length_b 15.89219(10) _cell_length_c 18.23835(15) _cell_angle_alpha 90 _cell_angle_beta 105.5221(8) _cell_angle_gamma 90 _cell_volume 2831.92(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 13174 _cell_measurement_temperature 180.01(10) _cell_measurement_theta_max 73.6670 _cell_measurement_theta_min 3.7150 _shelx_estimated_absorpt_T_max 0.775 _shelx_estimated_absorpt_T_min 0.585 _exptl_absorpt_coefficient_mu 1.411 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.261 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description prism _exptl_crystal_F_000 1200 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 -1 0.1410 0 -1 1 0.1410 -1 1 0 0.1593 1 -1 0 0.1593 1 0 -1 0.1832 -1 0 1 0.1832 0 1 1 0.0951 0 -1 -1 0.0951 _exptl_crystal_size_max 0.426 _exptl_crystal_size_mid 0.303 _exptl_crystal_size_min 0.19 loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.0000 1.0000 -1.0000 0.1271 0.0261 -0.0157 0.0000 -1.0000 1.0000 -0.1271 -0.0261 0.0157 -1.0000 1.0000 -0.0000 0.1214 -0.0053 0.1397 1.0000 -1.0000 0.0000 -0.1214 0.0053 -0.1397 1.0000 -0.0000 -1.0000 0.0057 0.0313 -0.1554 -1.0000 0.0000 1.0000 -0.0057 -0.0313 0.1554 -0.0000 1.0000 1.0000 0.0394 -0.1246 0.0020 0.0000 -1.0000 -1.0000 -0.0394 0.1246 -0.0020 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_unetI/netI 0.0189 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 19567 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.630 _diffrn_reflns_theta_min 3.750 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 180.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.4679 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -3.00 69.00 1.00 1.00 -- 38.94 -38.00 90.00 72 2 \w 4.00 49.00 1.00 1.00 -- 38.94 -99.00 90.00 45 3 \w 37.00 133.00 1.00 1.50 -- 110.40 -45.00 120.00 96 4 \w 54.00 171.00 1.00 1.50 -- 110.40 -15.00 -30.00 117 5 \w 117.00 169.00 1.00 1.50 -- 110.40 45.00-180.00 52 6 \w 132.00 173.00 1.00 1.50 -- 110.40 111.00-180.00 41 7 \w 103.00 132.00 1.00 1.50 -- 110.40 111.00-150.00 29 8 \w 61.00 148.00 1.00 1.50 -- 110.40 -30.00-180.00 87 9 \w 79.00 114.00 1.00 1.50 -- 110.40-111.00 -60.00 35 10 \w 68.00 109.00 1.00 1.50 -- 110.40 -94.00-180.00 41 11 \w 55.00 126.00 1.00 1.50 -- 110.40 -61.00-150.00 71 12 \w 89.00 117.00 1.00 1.00 -- 38.94-178.00-120.00 28 13 \w 37.00 115.00 1.00 1.50 -- 110.40-111.00 60.00 78 14 \w 26.00 73.00 1.00 1.50 -- 110.40 -77.00 90.00 47 15 \w 28.00 89.00 1.00 1.50 -- 110.40 -94.00 150.00 61 16 \w 100.00 177.00 1.00 1.50 -- 110.40 111.00 120.00 77 17 \w 71.00 132.00 1.00 1.00 -- 38.94 178.00 90.00 61 18 \w -114.00 -87.00 1.00 1.00 -- -38.94 -99.00-120.00 27 19 \w -113.00 -7.00 1.00 1.00 -- -38.94 -57.00-150.00 106 20 \w -111.00 -85.00 1.00 1.00 -- -38.94 -99.00 -30.00 26 21 \w -105.00 -80.00 1.00 1.00 -- -38.94 -99.00 30.00 25 22 \w -121.00 -83.00 1.00 1.00 -- -38.94 -99.00 -60.00 38 23 \w -114.00 -57.00 1.00 1.00 -- -38.94-151.00-142.00 57 24 \w -115.00 -81.00 1.00 1.00 -- -38.94 -99.00-150.00 34 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0381842000 _diffrn_orient_matrix_UB_12 0.0832339000 _diffrn_orient_matrix_UB_13 -0.0438836000 _diffrn_orient_matrix_UB_21 -0.0440069000 _diffrn_orient_matrix_UB_22 -0.0492578000 _diffrn_orient_matrix_UB_23 -0.0753442000 _diffrn_orient_matrix_UB_31 -0.1465168000 _diffrn_orient_matrix_UB_32 -0.0068359000 _diffrn_orient_matrix_UB_33 0.0088527000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 5173 _reflns_number_total 5648 _reflns_odcompleteness_completeness 99.96 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 67.29 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'SIR2004 (Burla et al., 2007)' _refine_diff_density_max 0.264 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.086 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 380 _refine_ls_number_reflns 5648 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0409 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+0.8235P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1056 _refine_ls_wR_factor_ref 0.1083 _refine_special_details ; The O-methyl group is disordered ans was refined using two components. Same distances restraints were applied and anisotropic displacement parameters of identical atoms were constrained to be identical. SADI O42 C37 O40 C37 SADI O40 C41 O42 C43 SADI 0.04 C41 C37 C37 C43 EADP O40 O42 EADP C41 C43 ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances O42-C37 \\sim O40-C37 with sigma of 0.02 O40-C41 \\sim O42-C43 with sigma of 0.02 C41-C37 \\sim C37-C43 with sigma of 0.04 3. Uiso/Uaniso restraints and constraints Uanis(O40) = Uanis(O42) Uanis(C41) = Uanis(C43) 4. Others Sof(O40)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(H41C)=1-FVAR(1) Sof(O42)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(H43C)=FVAR(1) 5.a Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C12(H12A,H12B), C17(H17A,H17B) 5.b Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C8(H8), C9(H9), C15(H15), C22(H22), C23(H23), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C38(H38), C39(H39) 5.c Idealised Me refined as rotating group: C25(H25A,H25B,H25C), C41(H41A,H41B,H41C), C43(H43A,H43B,H43C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary ? 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 S18 S 0.79337(3) 0.48139(2) 0.60565(2) 0.02526(10) Uani 1 1 d . . . . . O2 O 0.24106(18) 0.27590(9) 0.74207(10) 0.0745(5) Uani 1 1 d . . . . . O3 O 0.18546(19) 0.36228(10) 0.82069(10) 0.0749(5) Uani 1 1 d . . . . . O19 O 0.68444(11) 0.44613(6) 0.54667(6) 0.0352(2) Uani 1 1 d . . . . . O20 O 0.88325(11) 0.42727(6) 0.65888(6) 0.0351(2) Uani 1 1 d . . . . . O40 O 0.895(2) 0.9751(9) 0.5586(13) 0.0652(13) Uani 0.319(16) 1 d D . P A 2 O42 O 0.9266(10) 0.9621(4) 0.5613(6) 0.0652(13) Uani 0.681(16) 1 d D . P A 1 N1 N 0.24256(17) 0.34608(10) 0.77061(10) 0.0526(4) Uani 1 1 d . . . . . N10 N 0.50176(11) 0.60736(7) 0.65710(7) 0.0265(2) Uani 1 1 d . . . . . N13 N 0.72662(11) 0.71906(7) 0.72357(6) 0.0246(2) Uani 1 1 d . . . . . N16 N 0.71989(11) 0.54536(7) 0.65539(6) 0.0231(2) Uani 1 1 d . . . . . C4 C 0.31444(15) 0.41309(10) 0.74388(9) 0.0356(3) Uani 1 1 d . . . . . C5 C 0.30895(16) 0.49399(10) 0.77103(9) 0.0372(3) Uani 1 1 d . . . . . H5 H 0.261506 0.504982 0.808412 0.045 Uiso 1 1 calc R . . . . C6 C 0.37278(14) 0.55834(9) 0.74342(9) 0.0327(3) Uani 1 1 d . . . . . H6 H 0.368579 0.613996 0.761674 0.039 Uiso 1 1 calc R . . . . C7 C 0.44455(13) 0.54260(8) 0.68819(8) 0.0260(3) Uani 1 1 d . . . . . C8 C 0.45462(13) 0.45843(9) 0.66541(8) 0.0280(3) Uani 1 1 d . . . . . H8 H 0.507655 0.445711 0.631076 0.034 Uiso 1 1 calc R . . . . C9 C 0.38859(14) 0.39460(9) 0.69233(8) 0.0318(3) Uani 1 1 d . . . . . H9 H 0.393879 0.338373 0.675668 0.038 Uiso 1 1 calc R . . . . C11 C 0.48179(14) 0.69519(8) 0.67556(8) 0.0286(3) Uani 1 1 d . . . . . H11A H 0.392854 0.701087 0.687823 0.034 Uiso 1 1 calc R . . . . H11B H 0.479448 0.730993 0.630801 0.034 Uiso 1 1 calc R . . . . C12 C 0.59584(13) 0.72464(8) 0.74264(8) 0.0270(3) Uani 1 1 d . . . . . H12A H 0.578929 0.783531 0.755326 0.032 Uiso 1 1 calc R . . . . H12B H 0.598426 0.689147 0.787606 0.032 Uiso 1 1 calc R . . . . C14 C 0.81644(13) 0.65185(8) 0.75545(7) 0.0239(3) Uani 1 1 d . . . . . C15 C 0.80807(13) 0.57539(8) 0.72394(7) 0.0240(3) Uani 1 1 d . . . . . H15 H 0.871034 0.535172 0.751945 0.029 Uiso 1 1 calc R . . . . C17 C 0.59583(13) 0.59136(8) 0.61199(7) 0.0250(3) Uani 1 1 d . . . . . H17A H 0.623756 0.645569 0.593972 0.030 Uiso 1 1 calc R . . . . H17B H 0.549018 0.557875 0.566733 0.030 Uiso 1 1 calc R . . . . C21 C 0.89152(13) 0.54858(8) 0.56471(7) 0.0252(3) Uani 1 1 d . . . . . C22 C 0.82832(15) 0.59317(10) 0.49973(8) 0.0353(3) Uani 1 1 d . . . . . H22 H 0.734383 0.583942 0.474989 0.042 Uiso 1 1 calc R . . . . C23 C 0.90307(18) 0.65145(10) 0.47095(9) 0.0402(4) Uani 1 1 d . . . . . H23 H 0.859746 0.682091 0.426274 0.048 Uiso 1 1 calc R . . . . C24 C 1.04020(16) 0.66565(9) 0.50648(9) 0.0360(3) Uani 1 1 d . . . . . C25 C 1.1208(2) 0.72990(11) 0.47591(13) 0.0548(5) Uani 1 1 d . . . . . H25A H 1.168693 0.767312 0.517190 0.082 Uiso 1 1 calc GR . . . . H25B H 1.058511 0.763016 0.435979 0.082 Uiso 1 1 calc GR . . . . H25C H 1.187794 0.701190 0.454649 0.082 Uiso 1 1 calc GR . . . . C26 C 1.10176(16) 0.61932(10) 0.57063(10) 0.0409(4) Uani 1 1 d . . . . . H26 H 1.196126 0.627775 0.594832 0.049 Uiso 1 1 calc R . . . . C27 C 1.02889(15) 0.56074(10) 0.60050(9) 0.0346(3) Uani 1 1 d . . . . . H27 H 1.072496 0.529505 0.644762 0.042 Uiso 1 1 calc R . . . . C28 C 0.91940(14) 0.67050(9) 0.82870(8) 0.0290(3) Uani 1 1 d . . . . . C29 C 1.03870(19) 0.62407(14) 0.85442(11) 0.0586(6) Uani 1 1 d . . . . . H29 H 1.055866 0.578155 0.824914 0.070 Uiso 1 1 calc R . . . . C30 C 1.1333(2) 0.64368(15) 0.92253(12) 0.0684(7) Uani 1 1 d . . . . . H30 H 1.214736 0.611415 0.938939 0.082 Uiso 1 1 calc R . . . . C31 C 1.11016(18) 0.70956(12) 0.96665(9) 0.0473(4) Uani 1 1 d . . . . . H31 H 1.174133 0.722013 1.013865 0.057 Uiso 1 1 calc R . . . . C32 C 0.99331(17) 0.75711(10) 0.94150(8) 0.0376(3) Uani 1 1 d . . . . . H32 H 0.976819 0.802919 0.971323 0.045 Uiso 1 1 calc R . . . . C33 C 0.89943(15) 0.73844(9) 0.87275(8) 0.0311(3) Uani 1 1 d . . . . . H33 H 0.820267 0.772576 0.855473 0.037 Uiso 1 1 calc R . . . . C34 C 0.77301(14) 0.78401(8) 0.68495(7) 0.0270(3) Uani 1 1 d . . . . . C35 C 0.70512(19) 0.86091(9) 0.66979(9) 0.0407(4) Uani 1 1 d . . . . . H35 H 0.626041 0.870719 0.687102 0.049 Uiso 1 1 calc R . . . . C36 C 0.7518(2) 0.92353(10) 0.62959(11) 0.0533(5) Uani 1 1 d . . . . . H36 H 0.705290 0.975952 0.620367 0.064 Uiso 1 1 calc R . . . . C37 C 0.8652(2) 0.90989(10) 0.60310(10) 0.0495(5) Uani 1 1 d D . . . . C38 C 0.93334(18) 0.83387(10) 0.61761(9) 0.0416(4) Uani 1 1 d . . . . . H38 H 1.011731 0.824340 0.599604 0.050 Uiso 1 1 calc R . . . . C39 C 0.88857(15) 0.77159(9) 0.65807(8) 0.0322(3) Uani 1 1 d . . . . . H39 H 0.936759 0.719749 0.667749 0.039 Uiso 1 1 calc R . . . . C41 C 0.8054(19) 1.0434(8) 0.5282(10) 0.080(2) Uani 0.319(16) 1 d D . P A 2 H41A H 0.845310 1.077343 0.494693 0.120 Uiso 0.319(16) 1 calc GR . P A 2 H41B H 0.792760 1.078561 0.569975 0.120 Uiso 0.319(16) 1 calc GR . P A 2 H41C H 0.716651 1.021216 0.499152 0.120 Uiso 0.319(16) 1 calc GR . P A 2 C43 C 0.8731(12) 1.0460(3) 0.5532(5) 0.080(2) Uani 0.681(16) 1 d D . P A 1 H43A H 0.775815 1.044645 0.525639 0.120 Uiso 0.681(16) 1 calc GR . P A 1 H43B H 0.923105 1.080135 0.524813 0.120 Uiso 0.681(16) 1 calc GR . P A 1 H43C H 0.883617 1.070748 0.603702 0.120 Uiso 0.681(16) 1 calc GR . P A 1 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 S18 0.03137(18) 0.01908(16) 0.02846(18) -0.00393(11) 0.01346(13) -0.00229(11) O2 0.1025(12) 0.0407(7) 0.1049(13) -0.0116(8) 0.0703(11) -0.0295(8) O3 0.0994(12) 0.0633(9) 0.0878(11) -0.0120(8) 0.0694(10) -0.0335(9) O19 0.0392(6) 0.0317(5) 0.0382(6) -0.0151(4) 0.0163(4) -0.0111(4) O20 0.0472(6) 0.0220(5) 0.0406(6) 0.0036(4) 0.0198(5) 0.0073(4) O40 0.117(5) 0.027(2) 0.0742(12) 0.0070(16) 0.065(3) -0.0074(17) O42 0.117(5) 0.027(2) 0.0742(12) 0.0070(16) 0.065(3) -0.0074(17) N1 0.0589(9) 0.0444(8) 0.0664(10) -0.0015(7) 0.0371(8) -0.0182(7) N10 0.0266(5) 0.0215(5) 0.0332(6) -0.0019(4) 0.0110(4) -0.0009(4) N13 0.0275(5) 0.0200(5) 0.0272(5) 0.0003(4) 0.0088(4) -0.0010(4) N16 0.0262(5) 0.0211(5) 0.0234(5) -0.0029(4) 0.0090(4) -0.0001(4) C4 0.0331(7) 0.0337(8) 0.0428(8) 0.0031(6) 0.0150(6) -0.0082(6) C5 0.0330(7) 0.0408(8) 0.0434(8) -0.0026(7) 0.0199(6) -0.0034(6) C6 0.0302(7) 0.0307(7) 0.0400(8) -0.0047(6) 0.0142(6) -0.0012(5) C7 0.0214(6) 0.0259(6) 0.0300(7) -0.0007(5) 0.0057(5) -0.0017(5) C8 0.0271(6) 0.0261(6) 0.0315(7) -0.0025(5) 0.0091(5) -0.0028(5) C9 0.0315(7) 0.0263(7) 0.0379(7) -0.0013(6) 0.0097(6) -0.0050(5) C11 0.0278(6) 0.0214(6) 0.0373(7) -0.0002(5) 0.0101(5) 0.0027(5) C12 0.0318(7) 0.0213(6) 0.0306(6) -0.0015(5) 0.0131(5) 0.0009(5) C14 0.0261(6) 0.0243(6) 0.0226(6) 0.0002(5) 0.0086(5) -0.0004(5) C15 0.0267(6) 0.0238(6) 0.0227(6) 0.0018(5) 0.0088(5) 0.0011(5) C17 0.0272(6) 0.0240(6) 0.0238(6) 0.0006(5) 0.0068(5) -0.0011(5) C21 0.0296(6) 0.0216(6) 0.0271(6) -0.0038(5) 0.0125(5) -0.0011(5) C22 0.0340(7) 0.0415(8) 0.0299(7) 0.0029(6) 0.0078(6) -0.0027(6) C23 0.0504(9) 0.0387(8) 0.0349(8) 0.0083(6) 0.0174(7) 0.0019(7) C24 0.0458(8) 0.0246(6) 0.0470(8) -0.0043(6) 0.0286(7) -0.0024(6) C25 0.0750(13) 0.0314(8) 0.0759(13) -0.0033(8) 0.0511(11) -0.0094(8) C26 0.0304(7) 0.0398(8) 0.0545(10) -0.0010(7) 0.0147(7) -0.0051(6) C27 0.0292(7) 0.0352(7) 0.0391(8) 0.0045(6) 0.0085(6) 0.0013(6) C28 0.0303(7) 0.0306(7) 0.0255(6) -0.0034(5) 0.0063(5) -0.0004(5) C29 0.0472(10) 0.0655(12) 0.0497(10) -0.0289(9) -0.0104(8) 0.0240(9) C30 0.0528(11) 0.0766(14) 0.0568(12) -0.0245(11) -0.0186(9) 0.0282(10) C31 0.0486(9) 0.0512(10) 0.0323(8) -0.0092(7) -0.0060(7) 0.0013(8) C32 0.0481(9) 0.0343(7) 0.0285(7) -0.0064(6) 0.0066(6) -0.0038(6) C33 0.0358(7) 0.0287(7) 0.0278(7) -0.0032(5) 0.0069(5) -0.0009(6) C34 0.0376(7) 0.0213(6) 0.0221(6) -0.0033(5) 0.0082(5) -0.0063(5) C35 0.0634(10) 0.0242(7) 0.0416(8) 0.0016(6) 0.0262(8) 0.0029(7) C36 0.0971(15) 0.0223(7) 0.0511(10) 0.0043(7) 0.0382(10) 0.0026(8) C37 0.0865(13) 0.0304(8) 0.0406(9) -0.0023(7) 0.0325(9) -0.0188(8) C38 0.0542(9) 0.0396(8) 0.0365(8) -0.0053(6) 0.0218(7) -0.0173(7) C39 0.0379(7) 0.0307(7) 0.0290(7) -0.0031(5) 0.0109(6) -0.0078(6) C41 0.141(7) 0.0314(11) 0.086(4) 0.017(2) 0.064(4) -0.003(3) C43 0.141(7) 0.0314(11) 0.086(4) 0.017(2) 0.064(4) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 S18 O19 1.4335(10) . ? S18 O20 1.4281(11) . ? S18 N16 1.6655(11) . ? S18 C21 1.7567(13) . ? O2 N1 1.229(2) . ? O3 N1 1.232(2) . ? O40 C37 1.399(12) . ? O40 C41 1.430(13) . ? O42 C37 1.383(6) . ? O42 C43 1.432(6) . ? N1 C4 1.4468(19) . ? N10 C7 1.3760(17) . ? N10 C11 1.4627(16) . ? N10 C17 1.4393(17) . ? N13 C12 1.4608(16) . ? N13 C14 1.4230(16) . ? N13 C34 1.4001(16) . ? N16 C15 1.4114(16) . ? N16 C17 1.4867(16) . ? C4 C5 1.384(2) . ? C4 C9 1.383(2) . ? C5 H5 0.9500 . ? C5 C6 1.376(2) . ? C6 H6 0.9500 . ? C6 C7 1.4139(19) . ? C7 C8 1.4125(18) . ? C8 H8 0.9500 . ? C8 C9 1.3763(19) . ? C9 H9 0.9500 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.5153(19) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C14 C15 1.3372(18) . ? C14 C28 1.4887(18) . ? C15 H15 0.9500 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C21 C22 1.382(2) . ? C21 C27 1.385(2) . ? C22 H22 0.9500 . ? C22 C23 1.386(2) . ? C23 H23 0.9500 . ? C23 C24 1.386(2) . ? C24 C25 1.505(2) . ? C24 C26 1.382(2) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26 0.9500 . ? C26 C27 1.387(2) . ? C27 H27 0.9500 . ? C28 C29 1.387(2) . ? C28 C33 1.3926(19) . ? C29 H29 0.9500 . ? C29 C30 1.387(2) . ? C30 H30 0.9500 . ? C30 C31 1.378(3) . ? C31 H31 0.9500 . ? C31 C32 1.376(2) . ? C32 H32 0.9500 . ? C32 C33 1.388(2) . ? C33 H33 0.9500 . ? C34 C35 1.394(2) . ? C34 C39 1.400(2) . ? C35 H35 0.9500 . ? C35 C36 1.392(2) . ? C36 H36 0.9500 . ? C36 C37 1.378(3) . ? C37 C38 1.382(3) . ? C38 H38 0.9500 . ? C38 C39 1.382(2) . ? C39 H39 0.9500 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? 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 O19 S18 N16 106.26(6) . . ? O19 S18 C21 109.21(6) . . ? O20 S18 O19 119.88(6) . . ? O20 S18 N16 107.12(6) . . ? O20 S18 C21 108.91(6) . . ? N16 S18 C21 104.32(6) . . ? C37 O40 C41 124.9(13) . . ? C37 O42 C43 113.7(5) . . ? O2 N1 O3 123.26(15) . . ? O2 N1 C4 118.39(14) . . ? O3 N1 C4 118.35(15) . . ? C7 N10 C11 121.28(11) . . ? C7 N10 C17 121.37(11) . . ? C17 N10 C11 116.99(11) . . ? C14 N13 C12 118.09(10) . . ? C34 N13 C12 121.57(11) . . ? C34 N13 C14 119.63(11) . . ? C15 N16 S18 114.78(9) . . ? C15 N16 C17 123.41(10) . . ? C17 N16 S18 116.64(8) . . ? C5 C4 N1 119.41(14) . . ? C9 C4 N1 119.15(14) . . ? C9 C4 C5 121.44(13) . . ? C4 C5 H5 120.3 . . ? C6 C5 C4 119.45(14) . . ? C6 C5 H5 120.3 . . ? C5 C6 H6 119.6 . . ? C5 C6 C7 120.76(13) . . ? C7 C6 H6 119.6 . . ? N10 C7 C6 121.03(12) . . ? N10 C7 C8 121.03(12) . . ? C8 C7 C6 117.94(13) . . ? C7 C8 H8 119.6 . . ? C9 C8 C7 120.84(13) . . ? C9 C8 H8 119.6 . . ? C4 C9 H9 120.3 . . ? C8 C9 C4 119.38(13) . . ? C8 C9 H9 120.3 . . ? N10 C11 H11A 109.4 . . ? N10 C11 H11B 109.4 . . ? N10 C11 C12 110.97(11) . . ? H11A C11 H11B 108.0 . . ? C12 C11 H11A 109.4 . . ? C12 C11 H11B 109.4 . . ? N13 C12 C11 109.53(11) . . ? N13 C12 H12A 109.8 . . ? N13 C12 H12B 109.8 . . ? C11 C12 H12A 109.8 . . ? C11 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? N13 C14 C28 115.84(11) . . ? C15 C14 N13 123.12(12) . . ? C15 C14 C28 121.01(12) . . ? N16 C15 H15 115.1 . . ? C14 C15 N16 129.81(12) . . ? C14 C15 H15 115.1 . . ? N10 C17 N16 112.23(10) . . ? N10 C17 H17A 109.2 . . ? N10 C17 H17B 109.2 . . ? N16 C17 H17A 109.2 . . ? N16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C22 C21 S18 119.39(11) . . ? C22 C21 C27 120.65(13) . . ? C27 C21 S18 119.82(11) . . ? C21 C22 H22 120.3 . . ? C21 C22 C23 119.49(14) . . ? C23 C22 H22 120.3 . . ? C22 C23 H23 119.5 . . ? C22 C23 C24 120.90(14) . . ? C24 C23 H23 119.5 . . ? C23 C24 C25 120.90(16) . . ? C26 C24 C23 118.57(14) . . ? C26 C24 C25 120.53(16) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26 119.2 . . ? C24 C26 C27 121.51(14) . . ? C27 C26 H26 119.2 . . ? C21 C27 C26 118.87(14) . . ? C21 C27 H27 120.6 . . ? C26 C27 H27 120.6 . . ? C29 C28 C14 122.43(13) . . ? C29 C28 C33 117.76(13) . . ? C33 C28 C14 119.78(12) . . ? C28 C29 H29 119.5 . . ? C30 C29 C28 120.99(16) . . ? C30 C29 H29 119.5 . . ? C29 C30 H30 119.7 . . ? C31 C30 C29 120.59(17) . . ? C31 C30 H30 119.7 . . ? C30 C31 H31 120.4 . . ? C32 C31 C30 119.22(15) . . ? C32 C31 H31 120.4 . . ? C31 C32 H32 119.8 . . ? C31 C32 C33 120.31(14) . . ? C33 C32 H32 119.8 . . ? C28 C33 H33 119.5 . . ? C32 C33 C28 121.08(14) . . ? C32 C33 H33 119.5 . . ? C35 C34 N13 122.12(13) . . ? C35 C34 C39 118.01(13) . . ? C39 C34 N13 119.84(12) . . ? C34 C35 H35 119.6 . . ? C36 C35 C34 120.78(16) . . ? C36 C35 H35 119.6 . . ? C35 C36 H36 119.8 . . ? C37 C36 C35 120.36(16) . . ? C37 C36 H36 119.8 . . ? C36 C37 O40 114.7(6) . . ? C36 C37 O42 129.8(4) . . ? C36 C37 C38 119.46(15) . . ? C38 C37 O40 125.7(6) . . ? C38 C37 O42 110.8(4) . . ? C37 C38 H38 119.7 . . ? C37 C38 C39 120.64(16) . . ? C39 C38 H38 119.7 . . ? C34 C39 H39 119.6 . . ? C38 C39 C34 120.75(14) . . ? C38 C39 H39 119.6 . . ? O40 C41 H41A 109.5 . . ? O40 C41 H41B 109.5 . . ? O40 C41 H41C 109.5 . . ? H41A C41 H41B 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? O42 C43 H43A 109.5 . . ? O42 C43 H43B 109.5 . . ? O42 C43 H43C 109.5 . . ? H43A C43 H43B 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? _shelx_res_file ; TITL exp_2405_a.res in P2(1)/n exp_2405.res created by SHELXL-2017/1 at 10:38:53 on 04-Dec-2017 REM Old TITL exp_2405 in P2 REM SHELXT solution in P2(1)/n REM R1 0.163, Rweak 0.020, Alpha 0.035, Orientation as input REM Formula found by SHELXT: C34 N3 O3 Cl CELL 1.54184 10.140226 15.892192 18.23835 90 105.5221 90 ZERR 4 0.000077 0.000102 0.000148 0 0.0008 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O S UNIT 124 120 16 20 4 SADI O42 C37 O40 C37 SADI O40 C41 O42 C43 SADI 0.04 C41 C37 C37 C43 EADP O40 O42 EADP C41 C43 L.S. 4 PLAN 6 SIZE 0.19 0.303 0.426 TEMP -93 BOND $H LIST 4 fmap 2 acta REM REM REM WGHT 0.061800 0.823500 FVAR 4.44011 0.68075 S18 5 0.793373 0.481386 0.605647 11.00000 0.03137 0.01908 = 0.02846 -0.00393 0.01346 -0.00229 O2 4 0.241064 0.275895 0.742074 11.00000 0.10252 0.04074 = 0.10486 -0.01163 0.07026 -0.02952 O3 4 0.185458 0.362283 0.820694 11.00000 0.09939 0.06326 = 0.08775 -0.01197 0.06944 -0.03347 O19 4 0.684435 0.446132 0.546675 11.00000 0.03920 0.03170 = 0.03823 -0.01507 0.01628 -0.01114 O20 4 0.883247 0.427269 0.658883 11.00000 0.04720 0.02203 = 0.04059 0.00356 0.01976 0.00726 PART 2 O40 4 0.895180 0.975099 0.558626 -21.00000 0.11711 0.02697 = 0.07420 0.00697 0.06480 -0.00736 PART 0 PART 1 O42 4 0.926595 0.962144 0.561294 21.00000 0.11711 0.02697 = 0.07420 0.00697 0.06480 -0.00736 PART 0 N1 3 0.242559 0.346080 0.770611 11.00000 0.05888 0.04436 = 0.06639 -0.00149 0.03708 -0.01821 N10 3 0.501759 0.607357 0.657095 11.00000 0.02657 0.02151 = 0.03319 -0.00193 0.01103 -0.00091 N13 3 0.726616 0.719060 0.723568 11.00000 0.02750 0.02000 = 0.02719 0.00032 0.00883 -0.00101 N16 3 0.719887 0.545362 0.655388 11.00000 0.02623 0.02109 = 0.02342 -0.00288 0.00900 -0.00011 C4 1 0.314442 0.413091 0.743882 11.00000 0.03314 0.03374 = 0.04278 0.00312 0.01502 -0.00823 C5 1 0.308953 0.493987 0.771027 11.00000 0.03305 0.04076 = 0.04341 -0.00255 0.01989 -0.00341 AFIX 43 H5 2 0.261506 0.504982 0.808412 11.00000 -1.20000 AFIX 0 C6 1 0.372778 0.558343 0.743419 11.00000 0.03022 0.03066 = 0.04001 -0.00473 0.01417 -0.00124 AFIX 43 H6 2 0.368579 0.613996 0.761674 11.00000 -1.20000 AFIX 0 C7 1 0.444548 0.542602 0.688191 11.00000 0.02141 0.02593 = 0.02997 -0.00073 0.00567 -0.00174 C8 1 0.454623 0.458429 0.665413 11.00000 0.02714 0.02611 = 0.03150 -0.00253 0.00911 -0.00284 AFIX 43 H8 2 0.507655 0.445711 0.631076 11.00000 -1.20000 AFIX 0 C9 1 0.388591 0.394603 0.692331 11.00000 0.03145 0.02634 = 0.03787 -0.00126 0.00969 -0.00496 AFIX 43 H9 2 0.393879 0.338373 0.675668 11.00000 -1.20000 AFIX 0 C11 1 0.481789 0.695194 0.675555 11.00000 0.02776 0.02141 = 0.03730 -0.00020 0.01008 0.00268 AFIX 23 H11A 2 0.392854 0.701087 0.687823 11.00000 -1.20000 H11B 2 0.479448 0.730993 0.630801 11.00000 -1.20000 AFIX 0 C12 1 0.595844 0.724642 0.742636 11.00000 0.03175 0.02133 = 0.03060 -0.00148 0.01313 0.00091 AFIX 23 H12A 2 0.578929 0.783531 0.755326 11.00000 -1.20000 H12B 2 0.598426 0.689147 0.787606 11.00000 -1.20000 AFIX 0 C14 1 0.816444 0.651854 0.755451 11.00000 0.02606 0.02429 = 0.02263 0.00022 0.00858 -0.00042 C15 1 0.808070 0.575390 0.723939 11.00000 0.02670 0.02385 = 0.02272 0.00184 0.00879 0.00108 AFIX 43 H15 2 0.871034 0.535172 0.751945 11.00000 -1.20000 AFIX 0 C17 1 0.595834 0.591361 0.611988 11.00000 0.02724 0.02395 = 0.02380 0.00055 0.00683 -0.00111 AFIX 23 H17A 2 0.623756 0.645569 0.593972 11.00000 -1.20000 H17B 2 0.549018 0.557875 0.566733 11.00000 -1.20000 AFIX 0 C21 1 0.891517 0.548579 0.564706 11.00000 0.02962 0.02158 = 0.02707 -0.00384 0.01247 -0.00114 C22 1 0.828325 0.593174 0.499729 11.00000 0.03400 0.04150 = 0.02990 0.00292 0.00775 -0.00275 AFIX 43 H22 2 0.734383 0.583942 0.474989 11.00000 -1.20000 AFIX 0 C23 1 0.903068 0.651453 0.470953 11.00000 0.05041 0.03870 = 0.03489 0.00831 0.01743 0.00194 AFIX 43 H23 2 0.859746 0.682091 0.426274 11.00000 -1.20000 AFIX 0 C24 1 1.040198 0.665655 0.506480 11.00000 0.04576 0.02456 = 0.04702 -0.00433 0.02858 -0.00237 C25 1 1.120833 0.729898 0.475907 11.00000 0.07503 0.03142 = 0.07591 -0.00327 0.05114 -0.00938 AFIX 137 H25A 2 1.168693 0.767312 0.517190 11.00000 -1.50000 H25B 2 1.058511 0.763016 0.435979 11.00000 -1.50000 H25C 2 1.187794 0.701190 0.454649 11.00000 -1.50000 AFIX 0 C26 1 1.101757 0.619321 0.570632 11.00000 0.03042 0.03977 = 0.05450 -0.00097 0.01471 -0.00507 AFIX 43 H26 2 1.196126 0.627775 0.594832 11.00000 -1.20000 AFIX 0 C27 1 1.028885 0.560740 0.600503 11.00000 0.02918 0.03522 = 0.03910 0.00449 0.00848 0.00128 AFIX 43 H27 2 1.072496 0.529505 0.644762 11.00000 -1.20000 AFIX 0 C28 1 0.919402 0.670500 0.828705 11.00000 0.03030 0.03058 = 0.02553 -0.00340 0.00633 -0.00039 C29 1 1.038702 0.624075 0.854417 11.00000 0.04722 0.06549 = 0.04970 -0.02887 -0.01035 0.02400 AFIX 43 H29 2 1.055866 0.578155 0.824914 11.00000 -1.20000 AFIX 0 C30 1 1.133276 0.643681 0.922532 11.00000 0.05275 0.07665 = 0.05675 -0.02450 -0.01857 0.02824 AFIX 43 H30 2 1.214736 0.611415 0.938939 11.00000 -1.20000 AFIX 0 C31 1 1.110162 0.709564 0.966649 11.00000 0.04864 0.05116 = 0.03228 -0.00920 -0.00602 0.00126 AFIX 43 H31 2 1.174133 0.722013 1.013865 11.00000 -1.20000 AFIX 0 C32 1 0.993311 0.757111 0.941499 11.00000 0.04808 0.03426 = 0.02846 -0.00640 0.00663 -0.00376 AFIX 43 H32 2 0.976819 0.802919 0.971323 11.00000 -1.20000 AFIX 0 C33 1 0.899427 0.738443 0.872750 11.00000 0.03584 0.02869 = 0.02784 -0.00316 0.00691 -0.00091 AFIX 43 H33 2 0.820267 0.772576 0.855473 11.00000 -1.20000 AFIX 0 C34 1 0.773008 0.784014 0.684946 11.00000 0.03759 0.02129 = 0.02213 -0.00325 0.00821 -0.00633 C35 1 0.705122 0.860911 0.669793 11.00000 0.06340 0.02416 = 0.04157 0.00163 0.02620 0.00288 AFIX 43 H35 2 0.626041 0.870719 0.687102 11.00000 -1.20000 AFIX 0 C36 1 0.751824 0.923531 0.629589 11.00000 0.09714 0.02227 = 0.05112 0.00427 0.03821 0.00265 AFIX 43 H36 2 0.705290 0.975952 0.620367 11.00000 -1.20000 AFIX 0 C37 1 0.865171 0.909893 0.603098 11.00000 0.08651 0.03040 = 0.04060 -0.00229 0.03249 -0.01883 C38 1 0.933336 0.833875 0.617612 11.00000 0.05420 0.03962 = 0.03649 -0.00532 0.02179 -0.01732 AFIX 43 H38 2 1.011731 0.824340 0.599604 11.00000 -1.20000 AFIX 0 C39 1 0.888570 0.771589 0.658067 11.00000 0.03789 0.03071 = 0.02896 -0.00311 0.01085 -0.00776 AFIX 43 H39 2 0.936759 0.719749 0.667749 11.00000 -1.20000 AFIX 0 PART 2 C41 1 0.805412 1.043432 0.528219 -21.00000 0.14096 0.03141 = 0.08630 0.01719 0.06367 -0.00313 AFIX 137 H41A 2 0.845310 1.077343 0.494693 -21.00000 -1.50000 H41B 2 0.792760 1.078561 0.569975 -21.00000 -1.50000 H41C 2 0.716651 1.021216 0.499152 -21.00000 -1.50000 AFIX 0 PART 0 PART 1 C43 1 0.873057 1.046041 0.553225 21.00000 0.14096 0.03141 = 0.08630 0.01719 0.06367 -0.00313 AFIX 137 H43A 2 0.775815 1.044645 0.525639 21.00000 -1.50000 H43B 2 0.923105 1.080135 0.524813 21.00000 -1.50000 H43C 2 0.883617 1.070748 0.603702 21.00000 -1.50000 AFIX 0 HKLF 4 REM exp_2405_a.res in P2(1)/n REM R1 = 0.0409 for 5173 Fo > 4sig(Fo) and 0.0438 for all 5648 data REM 380 parameters refined using 3 restraints END WGHT 0.0618 0.8235 REM Highest difference peak 0.264, deepest hole -0.533, 1-sigma level 0.086 Q1 1 0.5381 1.0586 0.4950 11.00000 0.05 0.26 Q2 1 0.5887 1.0651 0.4307 11.00000 0.05 0.25 Q3 1 0.7788 1.0873 0.4341 11.00000 0.05 0.22 Q4 1 1.1134 0.7200 0.4131 11.00000 0.05 0.21 Q5 1 0.7984 1.0273 0.4242 11.00000 0.05 0.20 Q6 1 0.3731 0.5444 0.8808 11.00000 0.05 0.20 ; _shelx_res_checksum 1753 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.283 _oxdiff_exptl_absorpt_empirical_full_min 0.770 ####################################################################### # # 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_ajgi665_2_2 _database_code_depnum_ccdc_archive 'CCDC 2015201' loop_ _audit_author_name _audit_author_address 'Celine Besnard' ;university of Geneva Switzerland ; _audit_update_record ; 2020-07-09 deposited with the CCDC. 2020-11-23 downloaded from the CCDC. ; _audit_creation_date 2017-06-27 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _shelx_SHELXL_version_number 2016/6 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C32 H33 N3 O2 S' _chemical_formula_sum 'C32 H33 N3 O2 S' _chemical_formula_weight 523.67 _chemical_melting_point ? _chemical_oxdiff_formula 'C32 H33 N2 O2 S1' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'I 1 2/a 1' _space_group_name_Hall '-I 2ya' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 18.90952(14) _cell_length_b 10.14583(6) _cell_length_c 28.4275(2) _cell_angle_alpha 90 _cell_angle_beta 93.3559(7) _cell_angle_gamma 90 _cell_volume 5444.54(7) _cell_formula_units_Z 8 _cell_measurement_reflns_used 15287 _cell_measurement_temperature 180.00(10) _cell_measurement_theta_max 73.5070 _cell_measurement_theta_min 4.6030 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 1.322 _exptl_absorpt_correction_T_max 0.884 _exptl_absorpt_correction_T_min 0.714 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description prism _exptl_crystal_F_000 2224 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.0845 -1 0 0 0.0845 0 -1 -1 0.1385 0 1 1 0.1385 0 0 -1 0.0521 0 0 1 0.0521 _exptl_crystal_size_max 0.332 _exptl_crystal_size_mid 0.169 _exptl_crystal_size_min 0.104 loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0.9992 0.0003 0.0004 0.0146 -0.0298 -0.0745 -0.9992 -0.0003 -0.0004 -0.0146 0.0298 0.0745 0.0002 -0.9991 -1.0014 0.0946 -0.1119 0.0670 -0.0002 0.9991 1.0014 -0.0946 0.1119 -0.0670 -0.0000 0.0004 -0.9995 -0.0300 -0.0428 0.0147 0.0000 -0.0004 0.9995 0.0300 0.0428 -0.0147 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_unetI/netI 0.0136 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 23114 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.635 _diffrn_reflns_theta_min 3.114 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 180.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.4679 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -70.00 4.00 1.00 1.00 -- -38.94 38.00 150.00 74 2 \w 71.00 112.00 1.00 1.00 -- 38.94 178.00 120.00 41 3 \w 100.00 178.00 1.00 5.00 -- 110.40 111.00 30.00 78 4 \w 114.00 158.00 1.00 5.00 -- 110.40 111.00 -60.00 44 5 \w 99.00 156.00 1.00 5.00 -- 110.40 61.00 -60.00 57 6 \w 79.00 155.00 1.00 5.00 -- 110.40 45.00 0.00 76 7 \w 110.00 137.00 1.00 5.00 -- 110.40 -45.00 -30.00 27 8 \w 81.00 108.00 1.00 5.00 -- 110.40 -94.00 60.00 27 9 \w 66.00 113.00 1.00 5.00 -- 110.40-111.00 -30.00 47 10 \w 35.00 142.00 1.00 5.00 -- 110.40 -77.00 -30.00 107 11 \w 75.00 173.00 1.00 5.00 -- 110.40 30.00 -90.00 98 12 \w 84.00 176.00 1.00 5.00 -- 110.40 30.00 90.00 92 13 \w 60.00 131.00 1.00 1.00 -- 38.94 178.00 -90.00 71 14 \w 26.00 99.00 1.00 5.00 -- 110.40 -94.00 150.00 73 15 \w 30.00 56.00 1.00 5.00 -- 110.40-111.00 -30.00 26 16 \w 24.00 58.00 1.00 5.00 -- 110.40 -94.00 -30.00 34 17 \w 31.00 105.00 1.00 5.00 -- 110.40-111.00-120.00 74 18 \w -95.00 -10.00 1.00 1.00 -- -38.94 -38.00 -90.00 85 19 \w -111.00 -81.00 1.00 1.00 -- -38.94 -99.00 90.00 30 20 \w -115.00 -7.00 1.00 1.00 -- -38.94 -57.00 150.00 108 21 \w -123.00 -98.00 1.00 1.00 -- -38.94 -99.00 60.00 25 22 \w -124.00 -80.00 1.00 1.00 -- -38.94 -99.00-120.00 44 23 \w -62.00 -36.00 1.00 1.00 -- -38.94-178.00 -90.00 26 24 \w -124.00 -99.00 1.00 1.00 -- -38.94 -99.00 -30.00 25 25 \w -120.00 -94.00 1.00 1.00 -- -38.94-178.00 -90.00 26 26 \w 29.00 55.00 1.00 1.00 -- 38.94 38.00 -60.00 26 27 \w 63.00 89.00 1.00 1.00 -- 38.94 38.00 -60.00 26 28 \w 110.00 154.00 1.00 5.00 -- 110.40 111.00-180.00 44 29 \w 47.00 75.00 1.00 5.00 -- 110.40 -61.00-180.00 28 30 \w 148.00 174.00 1.00 5.00 -- 110.40 61.00 -30.00 26 31 \w 83.00 109.00 1.00 5.00 -- 110.40 61.00 -30.00 26 32 \w 114.00 140.00 1.00 5.00 -- 110.40 -61.00-180.00 26 33 \w 68.00 115.00 1.00 5.00 -- 110.40-111.00 120.00 47 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0146891000 _diffrn_orient_matrix_UB_12 -0.1246445000 _diffrn_orient_matrix_UB_13 0.0299326000 _diffrn_orient_matrix_UB_21 -0.0298941000 _diffrn_orient_matrix_UB_22 0.0691138000 _diffrn_orient_matrix_UB_23 0.0428140000 _diffrn_orient_matrix_UB_31 -0.0745196000 _diffrn_orient_matrix_UB_32 -0.0522985000 _diffrn_orient_matrix_UB_33 -0.0147620000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 5075 _reflns_number_total 5449 _reflns_odcompleteness_completeness 99.94 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 67.29 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _refine_diff_density_max 0.223 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.045 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 420 _refine_ls_number_reflns 5449 _refine_ls_number_restraints 180 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0348 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+3.4143P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0905 _refine_ls_wR_factor_ref 0.0926 _refine_special_details ; The methylphenyl group is disordered and was refined using two components. The following restraints/constraints were used: SADI C36B C35B C38 C35 SADI C37B C35B C34B C35B C35 C34 C35 C36 C38B C37B C34 C33 C33B C34B C33 C32 C33B C32 C38 C32 C37 C32 C36 C37 FLAT C36 C37 C32 C35 C34 C33 C38 FLAT C32 C33B C34 C35 C38 C36 C37 RIGU C33 C37 C34 C36 C35 C38 C32 RIGU C33B C38B C37B C35B C34B C36B C32 EADP C33B C33 The hydrogens bound to the carbon C9 are disordered. 6 hydrogen atoms were used with half occupancies and SADI restraints SADI C9 H9AB C9 H9BD C9 H9AC C9 H9AA C9 H9BE C9 H9BF ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C36B-C35B \\sim C38-C35 with sigma of 0.02 C37B-C35B \\sim C34B-C35B \\sim C35-C34 \\sim C35-C36 \\sim C38B-C37B \\sim C34-C33 \\sim C33B-C34B ~ C33-C32 \\sim C33B-C32 \\sim C38B-C32 \\sim C37-C32 \\sim C36-C37 with sigma of 0.02 C9-H9AB \\sim C9-H9BD \\sim C9-H9AC \\sim C9-H9AA \\sim C9-H9BE \\sim C9-H9BF with sigma of 0.02 3. Restrained planarity C32, C33, C34, C35, C36, C37, C38 with sigma of 0.1 C32, C33B, C34, C35, C36, C37, C38 with sigma of 0.1 4. Uiso/Uaniso restraints and constraints Uanis(C33B) = Uanis(C33) 5. Rigid body (RIGU) restrains C32, C33, C34, C35, C36, C37, C38 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 C32, C33B, C34B, C35B, C36B, C37B, C38B with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 6. Others Sof(C33B)=Sof(H33B)=Sof(C34B)=Sof(H34B)=Sof(C35B)=Sof(C36B)=Sof(H36A)= Sof(H36B)=Sof(H36C)=Sof(C37B)=Sof(H37B)=Sof(C38B)=Sof(H38B)=1-FVAR(1) Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(C36)=Sof(H36)=Sof(C37)= Sof(H37)=Sof(C38)=Sof(H38A)=Sof(H38C)=Sof(H38D)=FVAR(1) Fixed Sof: H9BD(0.5) H9BE(0.5) H9BF(0.5) H9AA(0.5) H9AB(0.5) H9AC(0.5) 7.a Ternary CH refined with riding coordinates: C5(H5) 7.b Secondary CH2 refined with riding coordinates: C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B) 7.c Aromatic/amide H refined with riding coordinates: C7(H7), C10(H10), C11(H11), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C30(H30), C31(H31), C33B(H33B), C34B(H34B), C37B(H37B), C38B(H38B), C33(H33), C34(H34), C36(H36), C37(H37) 7.d Idealised Me refined as rotating group: C29(H29A,H29B,H29C), C36B(H36A,H36B,H36C), C38(H38A,H38C,H38D) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary ? 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 0.60903(2) 0.57748(3) 0.52300(2) 0.02565(9) Uani 1 1 d . . . . . O2 O 0.65721(5) 0.68545(11) 0.52835(3) 0.0419(3) Uani 1 1 d . . . . . O3 O 0.57303(5) 0.55384(9) 0.47770(3) 0.0308(2) Uani 1 1 d . . . . . N4 N 0.54719(5) 0.59804(10) 0.55901(3) 0.0240(2) Uani 1 1 d . . . . . H4 H 0.5094(9) 0.5617(16) 0.5501(6) 0.037(4) Uiso 1 1 d . . . . . N13 N 0.52868(5) 0.67787(10) 0.68362(3) 0.0236(2) Uani 1 1 d . . . . . N16 N 0.43451(5) 0.45940(10) 0.67858(3) 0.0249(2) Uani 1 1 d . . . . . C5 C 0.56035(6) 0.65659(11) 0.60536(4) 0.0217(2) Uani 1 1 d . . . . . H5 H 0.612422 0.672801 0.610301 0.026 Uiso 1 1 calc R . . . . C6 C 0.52246(6) 0.78567(11) 0.61231(4) 0.0239(2) Uani 1 1 d . . . . . C7 C 0.50712(7) 0.88775(12) 0.58157(4) 0.0288(3) Uani 1 1 d . . . . . H7 H 0.520379 0.882518 0.549906 0.035 Uiso 1 1 calc R . . . . C8 C 0.47176(7) 0.99981(13) 0.59724(5) 0.0333(3) Uani 1 1 d . . . . . C9 C 0.45296(10) 1.11169(15) 0.56375(6) 0.0450(4) Uani 1 1 d D . . . . H9BD H 0.455(3) 1.198(3) 0.5797(15) 0.068 Uiso 0.5 1 d DR . P A 4 H9BE H 0.4052(16) 1.104(5) 0.5479(18) 0.068 Uiso 0.5 1 d DR . P B 4 H9BF H 0.484(2) 1.110(5) 0.5369(12) 0.068 Uiso 0.5 1 d DR . P C 4 H9AA H 0.432(2) 1.082(3) 0.5330(8) 0.038(9) Uiso 0.5 1 d D . P D 3 H9AB H 0.4931(16) 1.172(4) 0.5618(16) 0.052(10) Uiso 0.5 1 d D . P E 3 H9AC H 0.4121(18) 1.163(4) 0.5747(15) 0.052(11) Uiso 0.5 1 d D . P F 3 C10 C 0.45312(8) 1.00349(13) 0.64380(5) 0.0357(3) Uani 1 1 d . . . . . H10 H 0.429079 1.078879 0.654606 0.043 Uiso 1 1 calc R . . . . C11 C 0.46853(7) 0.90007(13) 0.67530(5) 0.0323(3) Uani 1 1 d . . . . . H11 H 0.454859 0.904272 0.706889 0.039 Uiso 1 1 calc R . . . . C12 C 0.50431(6) 0.79123(12) 0.65915(4) 0.0246(2) Uani 1 1 d . . . . . C14 C 0.49304(7) 0.63438(12) 0.72526(4) 0.0282(3) Uani 1 1 d . . . . . H14A H 0.484335 0.711709 0.745360 0.034 Uiso 1 1 calc R . . . . H14B H 0.524491 0.573072 0.743740 0.034 Uiso 1 1 calc R . . . . C15 C 0.42312(7) 0.56608(13) 0.71253(4) 0.0294(3) Uani 1 1 d . . . . . H15A H 0.403536 0.529171 0.741263 0.035 Uiso 1 1 calc R . . . . H15B H 0.388655 0.630461 0.698489 0.035 Uiso 1 1 calc R . . . . C17 C 0.46310(6) 0.51113(11) 0.63577(4) 0.0224(2) Uani 1 1 d . . . . . H17A H 0.430665 0.578750 0.621604 0.027 Uiso 1 1 calc R . . . . H17B H 0.467290 0.439122 0.612596 0.027 Uiso 1 1 calc R . . . . C18 C 0.53637(6) 0.57239(11) 0.64761(4) 0.0216(2) Uani 1 1 d . . . . . C19 C 0.59167(6) 0.47092(12) 0.66436(4) 0.0241(2) Uani 1 1 d . . . . . C20 C 0.65700(7) 0.51397(14) 0.68368(5) 0.0336(3) Uani 1 1 d . . . . . H20 H 0.665633 0.605785 0.687191 0.040 Uiso 1 1 calc R . . . . C21 C 0.70971(8) 0.42490(16) 0.69789(6) 0.0420(3) Uani 1 1 d . . . . . H21 H 0.754011 0.456110 0.710891 0.050 Uiso 1 1 calc R . . . . C22 C 0.69798(8) 0.29100(16) 0.69319(5) 0.0430(3) Uani 1 1 d . . . . . H22 H 0.734004 0.229917 0.702916 0.052 Uiso 1 1 calc R . . . . C23 C 0.63329(9) 0.24680(14) 0.67421(6) 0.0433(3) Uani 1 1 d . . . . . H23 H 0.624826 0.154877 0.670911 0.052 Uiso 1 1 calc R . . . . C24 C 0.58072(7) 0.33577(13) 0.65996(5) 0.0344(3) Uani 1 1 d . . . . . H24 H 0.536518 0.304001 0.646991 0.041 Uiso 1 1 calc R . . . . C25 C 0.37739(6) 0.36901(12) 0.67220(4) 0.0247(2) Uani 1 1 d . . . . . C26 C 0.35825(7) 0.29447(13) 0.71091(4) 0.0305(3) Uani 1 1 d . . . . . H26 H 0.383571 0.304910 0.740532 0.037 Uiso 1 1 calc R . . . . C27 C 0.30273(7) 0.20572(13) 0.70633(5) 0.0354(3) Uani 1 1 d . . . . . H27 H 0.290623 0.156156 0.733051 0.042 Uiso 1 1 calc R . . . . C28 C 0.26409(7) 0.18704(13) 0.66361(5) 0.0345(3) Uani 1 1 d . . . . . C29 C 0.20139(9) 0.09465(16) 0.66052(7) 0.0499(4) Uani 1 1 d . . . . . H29A H 0.216904 0.005868 0.669972 0.075 Uiso 1 1 calc GR . . . . H29B H 0.180966 0.092522 0.628037 0.075 Uiso 1 1 calc GR . . . . H29C H 0.165620 0.125586 0.681532 0.075 Uiso 1 1 calc GR . . . . C30 C 0.28473(7) 0.25772(13) 0.62508(5) 0.0335(3) Uani 1 1 d . . . . . H30 H 0.260290 0.244645 0.595285 0.040 Uiso 1 1 calc R . . . . C31 C 0.34056(6) 0.34767(12) 0.62895(4) 0.0286(3) Uani 1 1 d . . . . . H31 H 0.353581 0.394765 0.601896 0.034 Uiso 1 1 calc R . . . . C32 C 0.65543(7) 0.43261(16) 0.53897(5) 0.0380(3) Uani 1 1 d D U . . . C33B C 0.6224(11) 0.3113(12) 0.5333(4) 0.0579(5) Uani 0.387(18) 1 d D U P G 2 H33B H 0.573038 0.316160 0.525259 0.069 Uiso 0.387(18) 1 calc R . P G 2 C34B C 0.6489(6) 0.1830(11) 0.5374(4) 0.0499(19) Uani 0.387(18) 1 d D U P G 2 H34B H 0.621169 0.106875 0.530125 0.060 Uiso 0.387(18) 1 calc R . P G 2 C35B C 0.7196(6) 0.1776(11) 0.5531(4) 0.050(2) Uani 0.387(18) 1 d D U P G 2 C36B C 0.7620(8) 0.0501(11) 0.5567(5) 0.086(3) Uani 0.387(18) 1 d D U P G 2 H36A H 0.797050 0.049451 0.532588 0.128 Uiso 0.387(18) 1 calc GR . P G 2 H36B H 0.729989 -0.025207 0.551797 0.128 Uiso 0.387(18) 1 calc GR . P G 2 H36C H 0.786419 0.043953 0.587990 0.128 Uiso 0.387(18) 1 calc GR . P G 2 C37B C 0.7528(5) 0.2931(12) 0.5654(3) 0.048(2) Uani 0.387(18) 1 d D U P G 2 H37B H 0.800421 0.289553 0.578006 0.058 Uiso 0.387(18) 1 calc R . P G 2 C38B C 0.7205(5) 0.4146(11) 0.5606(4) 0.0441(18) Uani 0.387(18) 1 d D U P G 2 H38B H 0.745105 0.489623 0.573062 0.053 Uiso 0.387(18) 1 calc R . P G 2 C33 C 0.6227(7) 0.3122(8) 0.5327(3) 0.0579(5) Uani 0.613(18) 1 d D U P G 1 H33 H 0.575334 0.300398 0.520452 0.069 Uiso 0.613(18) 1 calc R . P G 1 C34 C 0.6690(5) 0.2086(9) 0.5470(3) 0.071(2) Uani 0.613(18) 1 d D U P G 1 H34 H 0.650105 0.121805 0.545464 0.086 Uiso 0.613(18) 1 calc R . P G 1 C35 C 0.7389(4) 0.2212(10) 0.5628(3) 0.057(2) Uani 0.613(18) 1 d D U P G 1 C36 C 0.7688(4) 0.3452(10) 0.5652(2) 0.0534(16) Uani 0.613(18) 1 d D U P G 1 H36 H 0.817221 0.355301 0.575340 0.064 Uiso 0.613(18) 1 calc R . P G 1 C37 C 0.7281(3) 0.4557(8) 0.5528(2) 0.0423(12) Uani 0.613(18) 1 d D U P G 1 H37 H 0.747739 0.541930 0.553544 0.051 Uiso 0.613(18) 1 calc R . P G 1 C38 C 0.7843(5) 0.1018(12) 0.5755(4) 0.108(4) Uani 0.613(18) 1 d D U P G 1 H38A H 0.789468 0.092901 0.609856 0.162 Uiso 0.613(18) 1 calc GR . P G 1 H38C H 0.831100 0.112752 0.562952 0.162 Uiso 0.613(18) 1 calc GR . P G 1 H38D H 0.761598 0.022554 0.561907 0.162 Uiso 0.613(18) 1 calc GR . P G 1 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 0.02312(15) 0.03466(17) 0.01949(15) -0.00345(10) 0.00394(10) -0.00365(11) O2 0.0366(5) 0.0551(6) 0.0350(5) -0.0106(4) 0.0104(4) -0.0208(5) O3 0.0314(4) 0.0417(5) 0.0192(4) -0.0020(3) 0.0020(3) -0.0054(4) N4 0.0209(5) 0.0305(5) 0.0206(5) -0.0051(4) 0.0022(4) -0.0022(4) N13 0.0285(5) 0.0243(5) 0.0180(4) -0.0020(4) 0.0020(4) -0.0006(4) N16 0.0253(5) 0.0292(5) 0.0205(5) -0.0013(4) 0.0040(4) -0.0030(4) C5 0.0224(5) 0.0236(5) 0.0191(5) -0.0015(4) 0.0005(4) -0.0007(4) C6 0.0250(5) 0.0235(5) 0.0232(5) -0.0018(4) 0.0018(4) -0.0012(4) C7 0.0338(6) 0.0270(6) 0.0257(6) 0.0010(5) 0.0034(5) -0.0007(5) C8 0.0397(7) 0.0239(6) 0.0364(7) 0.0018(5) 0.0029(5) 0.0013(5) C9 0.0589(10) 0.0293(7) 0.0474(9) 0.0088(6) 0.0072(7) 0.0088(7) C10 0.0449(7) 0.0240(6) 0.0388(7) -0.0049(5) 0.0075(6) 0.0054(5) C11 0.0424(7) 0.0275(6) 0.0276(6) -0.0067(5) 0.0067(5) 0.0005(5) C12 0.0274(6) 0.0236(5) 0.0227(5) -0.0024(4) 0.0001(4) -0.0022(4) C14 0.0357(6) 0.0311(6) 0.0180(5) -0.0014(4) 0.0031(4) -0.0024(5) C15 0.0323(6) 0.0335(6) 0.0231(6) -0.0033(5) 0.0072(5) -0.0020(5) C17 0.0227(5) 0.0255(5) 0.0190(5) -0.0002(4) 0.0015(4) -0.0009(4) C18 0.0228(5) 0.0236(5) 0.0184(5) -0.0021(4) 0.0010(4) -0.0003(4) C19 0.0251(5) 0.0272(6) 0.0201(5) 0.0008(4) 0.0018(4) 0.0019(5) C20 0.0299(6) 0.0335(7) 0.0365(7) 0.0006(5) -0.0048(5) 0.0000(5) C21 0.0306(7) 0.0508(9) 0.0433(8) 0.0005(6) -0.0095(6) 0.0061(6) C22 0.0420(8) 0.0442(8) 0.0421(8) 0.0030(6) -0.0043(6) 0.0189(6) C23 0.0489(8) 0.0292(7) 0.0511(9) 0.0010(6) -0.0021(7) 0.0104(6) C24 0.0333(6) 0.0289(6) 0.0404(7) -0.0002(5) -0.0039(5) 0.0017(5) C25 0.0219(5) 0.0250(5) 0.0274(6) 0.0018(4) 0.0038(4) 0.0018(4) C26 0.0308(6) 0.0337(6) 0.0273(6) 0.0047(5) 0.0055(5) 0.0025(5) C27 0.0352(7) 0.0320(6) 0.0403(7) 0.0083(5) 0.0138(6) 0.0005(5) C28 0.0286(6) 0.0260(6) 0.0496(8) 0.0002(5) 0.0084(5) -0.0017(5) C29 0.0413(8) 0.0388(8) 0.0705(11) -0.0010(7) 0.0119(8) -0.0139(7) C30 0.0303(6) 0.0306(6) 0.0390(7) -0.0004(5) -0.0028(5) -0.0031(5) C31 0.0285(6) 0.0278(6) 0.0293(6) 0.0044(5) 0.0004(5) -0.0018(5) C32 0.0342(7) 0.0549(9) 0.0257(6) -0.0004(6) 0.0082(5) 0.0157(6) C33B 0.0487(9) 0.0482(9) 0.0796(13) 0.0204(9) 0.0295(9) 0.0136(7) C34B 0.041(4) 0.038(3) 0.073(4) 0.014(3) 0.029(3) 0.004(3) C35B 0.052(5) 0.050(4) 0.049(4) 0.013(3) 0.020(3) 0.017(3) C36B 0.105(7) 0.068(5) 0.087(7) 0.032(4) 0.032(5) 0.052(5) C37B 0.033(4) 0.061(5) 0.051(3) 0.015(5) 0.004(3) 0.009(4) C38B 0.047(3) 0.051(4) 0.034(3) 0.009(3) 0.000(2) 0.007(3) C33 0.0487(9) 0.0482(9) 0.0796(13) 0.0204(9) 0.0295(9) 0.0136(7) C34 0.050(4) 0.049(3) 0.119(5) 0.035(3) 0.039(3) 0.008(3) C35 0.052(4) 0.068(4) 0.054(4) 0.029(4) 0.025(3) 0.027(3) C36 0.038(2) 0.079(4) 0.0425(17) -0.002(3) -0.0026(18) 0.024(2) C37 0.0354(17) 0.058(3) 0.032(2) -0.008(2) -0.0050(14) 0.0180(18) C38 0.102(5) 0.111(6) 0.117(6) 0.072(5) 0.061(5) 0.069(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O2 1.4273(10) . ? S1 O3 1.4410(9) . ? S1 N4 1.6121(10) . ? S1 C32 1.7578(15) . ? N4 H4 0.830(17) . ? N4 C5 1.4535(14) . ? N13 C12 1.4076(15) . ? N13 C14 1.4640(15) . ? N13 C18 1.4941(14) . ? N16 C15 1.4743(15) . ? N16 C17 1.4580(14) . ? N16 C25 1.4205(15) . ? C5 H5 1.0000 . ? C5 C6 1.5113(15) . ? C5 C18 1.5627(15) . ? C6 C7 1.3749(17) . ? C6 C12 1.3957(16) . ? C7 H7 0.9500 . ? C7 C8 1.4046(18) . ? C8 C9 1.5104(19) . ? C8 C10 1.3900(19) . ? C9 H9BD 0.987(18) . ? C9 H9BE 0.990(18) . ? C9 H9BF 0.987(18) . ? C9 H9AA 0.987(17) . ? C9 H9AB 0.979(17) . ? C9 H9AC 0.995(17) . ? C10 H10 0.9500 . ? C10 C11 1.3990(19) . ? C11 H11 0.9500 . ? C11 C12 1.3872(17) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 C15 1.5177(17) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 C18 1.5377(15) . ? C18 C19 1.5238(15) . ? C19 C20 1.3925(17) . ? C19 C24 1.3913(18) . ? C20 H20 0.9500 . ? C20 C21 1.3877(19) . ? C21 H21 0.9500 . ? C21 C22 1.382(2) . ? C22 H22 0.9500 . ? C22 C23 1.383(2) . ? C23 H23 0.9500 . ? C23 C24 1.3855(19) . ? C24 H24 0.9500 . ? C25 C26 1.4001(17) . ? C25 C31 1.3942(17) . ? C26 H26 0.9500 . ? C26 C27 1.3834(19) . ? C27 H27 0.9500 . ? C27 C28 1.393(2) . ? C28 C29 1.5099(19) . ? C28 C30 1.384(2) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30 0.9500 . ? C30 C31 1.3950(17) . ? C31 H31 0.9500 . ? C32 C33B 1.385(12) . ? C32 C38B 1.355(9) . ? C32 C33 1.376(8) . ? C32 C37 1.426(5) . ? C33B H33B 0.9500 . ? C33B C34B 1.397(12) . ? C34B H34B 0.9500 . ? C34B C35B 1.384(9) . ? C35B C36B 1.522(10) . ? C35B C37B 1.366(8) . ? C36B H36A 0.9800 . ? C36B H36B 0.9800 . ? C36B H36C 0.9800 . ? C37B H37B 0.9500 . ? C37B C38B 1.380(9) . ? C38B H38B 0.9500 . ? C33 H33 0.9500 . ? C33 C34 1.412(10) . ? C34 H34 0.9500 . ? C34 C35 1.378(7) . ? C35 C36 1.379(6) . ? C35 C38 1.516(6) . ? C36 H36 0.9500 . ? C36 C37 1.393(6) . ? C37 H37 0.9500 . ? C38 H38A 0.9800 . ? C38 H38C 0.9800 . ? C38 H38D 0.9800 . ? 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 O2 S1 O3 119.23(6) . . ? O2 S1 N4 108.37(6) . . ? O2 S1 C32 107.96(7) . . ? O3 S1 N4 105.47(5) . . ? O3 S1 C32 107.11(6) . . ? N4 S1 C32 108.29(6) . . ? S1 N4 H4 113.0(12) . . ? C5 N4 S1 122.44(8) . . ? C5 N4 H4 123.9(12) . . ? C12 N13 C14 119.54(10) . . ? C12 N13 C18 106.79(9) . . ? C14 N13 C18 113.95(9) . . ? C17 N16 C15 110.96(9) . . ? C25 N16 C15 114.72(9) . . ? C25 N16 C17 116.25(9) . . ? N4 C5 H5 108.0 . . ? N4 C5 C6 114.54(9) . . ? N4 C5 C18 115.55(9) . . ? C6 C5 H5 108.0 . . ? C6 C5 C18 102.24(9) . . ? C18 C5 H5 108.0 . . ? C7 C6 C5 130.82(11) . . ? C7 C6 C12 121.42(11) . . ? C12 C6 C5 107.74(10) . . ? C6 C7 H7 120.2 . . ? C6 C7 C8 119.66(12) . . ? C8 C7 H7 120.2 . . ? C7 C8 C9 120.49(13) . . ? C10 C8 C7 118.40(12) . . ? C10 C8 C9 121.09(13) . . ? C8 C9 H9BD 112(3) . . ? C8 C9 H9BE 114(3) . . ? C8 C9 H9BF 110(3) . . ? C8 C9 H9AA 114(2) . . ? C8 C9 H9AB 111(2) . . ? C8 C9 H9AC 111(2) . . ? H9BD C9 H9BE 107(4) . . ? H9BD C9 H9BF 111(4) . . ? H9BE C9 H9BF 102(4) . . ? H9AA C9 H9AB 115(3) . . ? H9AA C9 H9AC 98(3) . . ? H9AB C9 H9AC 108(3) . . ? C8 C10 H10 118.8 . . ? C8 C10 C11 122.30(12) . . ? C11 C10 H10 118.8 . . ? C10 C11 H11 120.9 . . ? C12 C11 C10 118.21(12) . . ? C12 C11 H11 120.9 . . ? C6 C12 N13 110.30(10) . . ? C11 C12 N13 129.71(11) . . ? C11 C12 C6 119.98(11) . . ? N13 C14 H14A 109.1 . . ? N13 C14 H14B 109.1 . . ? N13 C14 C15 112.37(10) . . ? H14A C14 H14B 107.9 . . ? C15 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? N16 C15 C14 109.43(10) . . ? N16 C15 H15A 109.8 . . ? N16 C15 H15B 109.8 . . ? C14 C15 H15A 109.8 . . ? C14 C15 H15B 109.8 . . ? H15A C15 H15B 108.2 . . ? N16 C17 H17A 109.7 . . ? N16 C17 H17B 109.7 . . ? N16 C17 C18 109.64(9) . . ? H17A C17 H17B 108.2 . . ? C18 C17 H17A 109.7 . . ? C18 C17 H17B 109.7 . . ? N13 C18 C5 100.33(8) . . ? N13 C18 C17 108.48(9) . . ? N13 C18 C19 111.24(9) . . ? C17 C18 C5 110.55(9) . . ? C19 C18 C5 112.64(9) . . ? C19 C18 C17 112.86(9) . . ? C20 C19 C18 119.22(11) . . ? C24 C19 C18 122.82(11) . . ? C24 C19 C20 117.94(12) . . ? C19 C20 H20 119.5 . . ? C21 C20 C19 121.06(13) . . ? C21 C20 H20 119.5 . . ? C20 C21 H21 119.9 . . ? C22 C21 C20 120.24(14) . . ? C22 C21 H21 119.9 . . ? C21 C22 H22 120.3 . . ? C21 C22 C23 119.34(13) . . ? C23 C22 H22 120.3 . . ? C22 C23 H23 119.8 . . ? C22 C23 C24 120.40(14) . . ? C24 C23 H23 119.8 . . ? C19 C24 H24 119.5 . . ? C23 C24 C19 121.02(13) . . ? C23 C24 H24 119.5 . . ? C26 C25 N16 118.56(11) . . ? C31 C25 N16 123.34(11) . . ? C31 C25 C26 118.07(11) . . ? C25 C26 H26 119.8 . . ? C27 C26 C25 120.49(12) . . ? C27 C26 H26 119.8 . . ? C26 C27 H27 119.1 . . ? C26 C27 C28 121.79(12) . . ? C28 C27 H27 119.1 . . ? C27 C28 C29 120.34(13) . . ? C30 C28 C27 117.49(12) . . ? C30 C28 C29 122.16(14) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30 119.2 . . ? C28 C30 C31 121.57(12) . . ? C31 C30 H30 119.2 . . ? C25 C31 C30 120.52(12) . . ? C25 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C33B C32 S1 119.9(9) . . ? C38B C32 S1 131.0(5) . . ? C38B C32 C33B 108.9(11) . . ? C33 C32 S1 119.7(6) . . ? C33 C32 C37 126.9(6) . . ? C37 C32 S1 113.1(4) . . ? C32 C33B H33B 114.3 . . ? C32 C33B C34B 131.4(17) . . ? C34B C33B H33B 114.3 . . ? C33B C34B H34B 123.3 . . ? C35B C34B C33B 113.5(11) . . ? C35B C34B H34B 123.3 . . ? C34B C35B C36B 123.4(8) . . ? C37B C35B C34B 118.0(7) . . ? C37B C35B C36B 118.6(8) . . ? C35B C36B H36A 109.5 . . ? C35B C36B H36B 109.5 . . ? C35B C36B H36C 109.5 . . ? H36A C36B H36B 109.5 . . ? H36A C36B H36C 109.5 . . ? H36B C36B H36C 109.5 . . ? C35B C37B H37B 118.4 . . ? C35B C37B C38B 123.2(8) . . ? C38B C37B H37B 118.4 . . ? C32 C38B C37B 123.4(8) . . ? C32 C38B H38B 118.3 . . ? C37B C38B H38B 118.3 . . ? C32 C33 H33 124.5 . . ? C32 C33 C34 111.0(10) . . ? C34 C33 H33 124.5 . . ? C33 C34 H34 116.9 . . ? C35 C34 C33 126.2(7) . . ? C35 C34 H34 116.9 . . ? C34 C35 C36 118.9(5) . . ? C34 C35 C38 121.5(6) . . ? C36 C35 C38 119.6(5) . . ? C35 C36 H36 119.9 . . ? C35 C36 C37 120.3(5) . . ? C37 C36 H36 119.9 . . ? C32 C37 H37 121.8 . . ? C36 C37 C32 116.5(4) . . ? C36 C37 H37 121.8 . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38C 109.5 . . ? C35 C38 H38D 109.5 . . ? H38A C38 H38C 109.5 . . ? H38A C38 H38D 109.5 . . ? H38C C38 H38D 109.5 . . ? _shelx_res_file ; TITL ajgi665_2_2_a.res in I2/a ajgi665_2_2.res created by SHELXL-2016/6 at 15:32:59 on 27-Jun-2017 REM Old TITL AJGI665_2_2 in I2/a REM SHELXT solution in I2/a REM R1 0.155, Rweak 0.027, Alpha 0.045, Orientation as input REM Formula found by SHELXT: C31 N3 O2 Cl CELL 1.54184 18.90952 10.145831 28.427502 90 93.3559 90 ZERR 8 0.000138 0.000063 0.000204 0 0.0007 0 LATT 2 SYMM 0.5-X,+Y,-Z SFAC C H N O S UNIT 256 264 24 16 8 SADI C36B C35B C38 C35 SADI C37B C35B C34B C35B C35 C34 C35 C36 C38B C37B C34 C33 C33B C34B C33 C32 = C33B C32 C38B C32 C37 C32 C36 C37 SADI C9 H9ab C9 H9bd C9 H9ac C9 H9aa C9 H9be C9 H9bf FLAT C32 C33 C34 C35 C36 C37 C38 FLAT C32 C33B C34 C35 C36 C37 C38 RIGU C32 C33 C34 C35 C36 C37 C38 RIGU C32 C33B C34B C35B C36B C37B C38B EADP C33B C33 L.S. 50 PLAN 20 TEMP -93 BOND $H LIST 6 fmap 2 acta REM REM REM WGHT 0.047100 3.414300 FVAR 2.36209 0.61275 S1 5 0.609026 0.577479 0.522996 11.00000 0.02312 0.03466 = 0.01949 -0.00345 0.00394 -0.00365 O2 4 0.657208 0.685451 0.528352 11.00000 0.03665 0.05508 = 0.03496 -0.01060 0.01043 -0.02077 O3 4 0.573027 0.553843 0.477698 11.00000 0.03142 0.04172 = 0.01923 -0.00202 0.00199 -0.00544 N4 3 0.547188 0.598041 0.559007 11.00000 0.02094 0.03053 = 0.02061 -0.00510 0.00221 -0.00221 H4 2 0.509430 0.561650 0.550057 11.00000 0.03717 N13 3 0.528677 0.677873 0.683624 11.00000 0.02854 0.02429 = 0.01798 -0.00203 0.00199 -0.00059 N16 3 0.434513 0.459404 0.678577 11.00000 0.02525 0.02915 = 0.02054 -0.00125 0.00397 -0.00302 C5 1 0.560354 0.656592 0.605358 11.00000 0.02239 0.02361 = 0.01913 -0.00147 0.00049 -0.00072 AFIX 13 H5 2 0.612422 0.672801 0.610301 11.00000 -1.20000 AFIX 0 C6 1 0.522461 0.785668 0.612309 11.00000 0.02496 0.02350 = 0.02321 -0.00185 0.00176 -0.00121 C7 1 0.507124 0.887750 0.581575 11.00000 0.03382 0.02704 = 0.02570 0.00102 0.00343 -0.00074 AFIX 43 H7 2 0.520379 0.882518 0.549906 11.00000 -1.20000 AFIX 0 C8 1 0.471761 0.999806 0.597237 11.00000 0.03975 0.02387 = 0.03638 0.00183 0.00290 0.00130 C9 1 0.452959 1.111690 0.563755 11.00000 0.05888 0.02930 = 0.04735 0.00878 0.00719 0.00884 PART 4 H9BD 2 0.455288 1.198123 0.579679 10.50000 -1.50000 H9BE 2 0.405159 1.104194 0.547858 10.50000 -1.50000 H9BF 2 0.483664 1.110306 0.536866 10.50000 -1.50000 PART 0 PART 3 H9AA 2 0.431625 1.082432 0.533005 10.50000 0.03846 H9AB 2 0.493095 1.171928 0.561769 10.50000 0.05247 H9AC 2 0.412053 1.162608 0.574673 10.50000 0.05248 PART 0 C10 1 0.453123 1.003494 0.643796 11.00000 0.04487 0.02400 = 0.03880 -0.00493 0.00746 0.00535 AFIX 43 H10 2 0.429079 1.078879 0.654606 11.00000 -1.20000 AFIX 0 C11 1 0.468532 0.900072 0.675296 11.00000 0.04241 0.02747 = 0.02760 -0.00671 0.00666 0.00050 AFIX 43 H11 2 0.454859 0.904272 0.706889 11.00000 -1.20000 AFIX 0 C12 1 0.504314 0.791228 0.659154 11.00000 0.02737 0.02365 = 0.02267 -0.00245 0.00007 -0.00216 C14 1 0.493035 0.634380 0.725260 11.00000 0.03571 0.03113 = 0.01797 -0.00141 0.00314 -0.00239 AFIX 23 H14A 2 0.484335 0.711709 0.745360 11.00000 -1.20000 H14B 2 0.524491 0.573072 0.743740 11.00000 -1.20000 AFIX 0 C15 1 0.423116 0.566079 0.712525 11.00000 0.03230 0.03354 = 0.02313 -0.00329 0.00725 -0.00203 AFIX 23 H15A 2 0.403536 0.529171 0.741263 11.00000 -1.20000 H15B 2 0.388655 0.630461 0.698489 11.00000 -1.20000 AFIX 0 C17 1 0.463102 0.511131 0.635769 11.00000 0.02270 0.02553 = 0.01899 -0.00018 0.00154 -0.00088 AFIX 23 H17A 2 0.430665 0.578750 0.621604 11.00000 -1.20000 H17B 2 0.467290 0.439122 0.612596 11.00000 -1.20000 AFIX 0 C18 1 0.536370 0.572388 0.647609 11.00000 0.02276 0.02358 = 0.01842 -0.00208 0.00098 -0.00032 C19 1 0.591673 0.470918 0.664364 11.00000 0.02511 0.02717 = 0.02005 0.00080 0.00180 0.00189 C20 1 0.657003 0.513967 0.683682 11.00000 0.02989 0.03346 = 0.03652 0.00064 -0.00480 0.00001 AFIX 43 H20 2 0.665633 0.605785 0.687191 11.00000 -1.20000 AFIX 0 C21 1 0.709706 0.424904 0.697889 11.00000 0.03057 0.05076 = 0.04334 0.00046 -0.00952 0.00608 AFIX 43 H21 2 0.754011 0.456110 0.710891 11.00000 -1.20000 AFIX 0 C22 1 0.697978 0.291000 0.693195 11.00000 0.04196 0.04419 = 0.04209 0.00302 -0.00427 0.01885 AFIX 43 H22 2 0.734004 0.229917 0.702916 11.00000 -1.20000 AFIX 0 C23 1 0.633286 0.246804 0.674209 11.00000 0.04891 0.02924 = 0.05109 0.00102 -0.00206 0.01038 AFIX 43 H23 2 0.624826 0.154877 0.670911 11.00000 -1.20000 AFIX 0 C24 1 0.580721 0.335772 0.659964 11.00000 0.03334 0.02886 = 0.04035 -0.00024 -0.00391 0.00170 AFIX 43 H24 2 0.536518 0.304001 0.646991 11.00000 -1.20000 AFIX 0 C25 1 0.377387 0.369010 0.672203 11.00000 0.02187 0.02495 = 0.02745 0.00178 0.00384 0.00181 C26 1 0.358247 0.294467 0.710908 11.00000 0.03085 0.03374 = 0.02728 0.00473 0.00555 0.00252 AFIX 43 H26 2 0.383571 0.304910 0.740532 11.00000 -1.20000 AFIX 0 C27 1 0.302729 0.205716 0.706332 11.00000 0.03524 0.03196 = 0.04029 0.00834 0.01381 0.00046 AFIX 43 H27 2 0.290623 0.156156 0.733051 11.00000 -1.20000 AFIX 0 C28 1 0.264088 0.187041 0.663606 11.00000 0.02862 0.02598 = 0.04964 0.00020 0.00839 -0.00168 C29 1 0.201394 0.094648 0.660516 11.00000 0.04132 0.03881 = 0.07048 -0.00098 0.01191 -0.01391 AFIX 137 H29A 2 0.216904 0.005868 0.669972 11.00000 -1.50000 H29B 2 0.180966 0.092522 0.628037 11.00000 -1.50000 H29C 2 0.165620 0.125586 0.681532 11.00000 -1.50000 AFIX 0 C30 1 0.284729 0.257717 0.625076 11.00000 0.03032 0.03055 = 0.03901 -0.00043 -0.00277 -0.00313 AFIX 43 H30 2 0.260290 0.244645 0.595285 11.00000 -1.20000 AFIX 0 C31 1 0.340556 0.347672 0.628947 11.00000 0.02850 0.02785 = 0.02926 0.00444 0.00040 -0.00182 AFIX 43 H31 2 0.353581 0.394765 0.601896 11.00000 -1.20000 AFIX 0 C32 1 0.655430 0.432608 0.538972 11.00000 0.03419 0.05494 = 0.02568 -0.00039 0.00816 0.01569 PART 2 C33B 1 0.622436 0.311280 0.533328 -21.00000 0.04875 0.04823 = 0.07964 0.02039 0.02948 0.01357 AFIX 43 H33B 2 0.573038 0.316160 0.525259 -21.00000 -1.20000 AFIX 0 C34B 1 0.648942 0.183008 0.537400 -21.00000 0.04130 0.03847 = 0.07310 0.01435 0.02940 0.00442 AFIX 43 H34B 2 0.621169 0.106875 0.530125 -21.00000 -1.20000 AFIX 0 C35B 1 0.719599 0.177562 0.553064 -21.00000 0.05161 0.04970 = 0.04935 0.01338 0.02007 0.01718 C36B 1 0.762045 0.050084 0.556682 -21.00000 0.10464 0.06845 = 0.08690 0.03180 0.03226 0.05189 AFIX 137 H36A 2 0.797050 0.049451 0.532588 -21.00000 -1.50000 H36B 2 0.729989 -0.025207 0.551797 -21.00000 -1.50000 H36C 2 0.786419 0.043953 0.587990 -21.00000 -1.50000 AFIX 0 C37B 1 0.752785 0.293069 0.565445 -21.00000 0.03298 0.06126 = 0.05132 0.01528 0.00446 0.00904 AFIX 43 H37B 2 0.800421 0.289553 0.578006 -21.00000 -1.20000 AFIX 0 C38B 1 0.720462 0.414624 0.560590 -21.00000 0.04683 0.05117 = 0.03397 0.00875 0.00036 0.00713 AFIX 43 H38B 2 0.745105 0.489623 0.573062 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C33 1 0.622728 0.312214 0.532716 21.00000 0.04875 0.04823 = 0.07964 0.02039 0.02948 0.01357 AFIX 43 H33 2 0.575334 0.300398 0.520452 21.00000 -1.20000 AFIX 0 C34 1 0.669002 0.208562 0.546954 21.00000 0.05006 0.04887 = 0.11918 0.03526 0.03908 0.00833 AFIX 43 H34 2 0.650105 0.121805 0.545464 21.00000 -1.20000 AFIX 0 C35 1 0.738928 0.221197 0.562799 21.00000 0.05202 0.06832 = 0.05450 0.02896 0.02540 0.02698 C36 1 0.768758 0.345194 0.565200 21.00000 0.03814 0.07896 = 0.04245 -0.00207 -0.00261 0.02402 AFIX 43 H36 2 0.817221 0.355301 0.575340 21.00000 -1.20000 AFIX 0 C37 1 0.728102 0.455718 0.552813 21.00000 0.03545 0.05848 = 0.03227 -0.00847 -0.00502 0.01803 AFIX 43 H37 2 0.747739 0.541930 0.553544 21.00000 -1.20000 AFIX 0 C38 1 0.784280 0.101803 0.575501 21.00000 0.10196 0.11100 = 0.11698 0.07225 0.06060 0.06945 AFIX 137 H38A 2 0.789468 0.092901 0.609856 21.00000 -1.50000 H38C 2 0.831100 0.112752 0.562952 21.00000 -1.50000 H38D 2 0.761598 0.022554 0.561907 21.00000 -1.50000 AFIX 0 HKLF 4 REM ajgi665_2_2_a.res in I2/a REM R1 = 0.0348 for 5075 Fo > 4sig(Fo) and 0.0372 for all 5449 data REM 420 parameters refined using 180 restraints END WGHT 0.0471 3.4143 REM Highest difference peak 0.223, deepest hole -0.434, 1-sigma level 0.045 Q1 1 0.5008 0.5429 0.6406 11.00000 0.05 0.22 Q2 1 0.5411 0.7269 0.6061 11.00000 0.05 0.21 Q3 1 0.5657 0.5217 0.6549 11.00000 0.05 0.19 Q4 1 0.5494 0.6070 0.6257 11.00000 0.05 0.19 Q5 1 0.6342 0.4970 0.5331 11.00000 0.05 0.19 Q6 1 0.2924 0.1796 0.6796 11.00000 0.05 0.18 Q7 1 0.5110 0.7433 0.6729 11.00000 0.05 0.18 Q8 1 0.2630 0.2481 0.6486 11.00000 0.05 0.18 Q9 1 0.5002 0.8530 0.6716 11.00000 0.05 0.18 Q10 1 0.5043 0.7794 0.6323 11.00000 0.05 0.17 Q11 1 0.5744 0.5776 0.5484 11.00000 0.05 0.17 Q12 1 0.7500 -0.1094 0.5000 10.50000 0.05 0.17 Q13 1 0.1982 0.0473 0.7002 11.00000 0.05 0.17 Q14 1 0.5114 0.6584 0.7024 11.00000 0.05 0.17 Q15 1 0.2141 0.0088 0.6415 11.00000 0.05 0.17 Q16 1 0.3101 0.2995 0.6275 11.00000 0.05 0.16 Q17 1 0.4584 0.6008 0.7184 11.00000 0.05 0.16 Q18 1 0.3648 0.3412 0.6482 11.00000 0.05 0.15 Q19 1 0.3214 0.2809 0.7103 11.00000 0.05 0.15 Q20 1 0.3706 0.3265 0.6924 11.00000 0.05 0.15 ; _shelx_res_checksum 82109 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.487 _oxdiff_exptl_absorpt_empirical_full_min 0.670 ####################################################################### # # 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_ajgi-665-23 _database_code_depnum_ccdc_archive 'CCDC 2015202' loop_ _audit_author_name _audit_author_address 'Celine Besnard' ;university of Geneva Switzerland ; _audit_update_record ; 2020-07-09 deposited with the CCDC. 2020-11-23 downloaded from the CCDC. ; _audit_creation_date 2017-07-11 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _shelx_SHELXL_version_number 2017/1 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C32 H33 N3 O2 S' _chemical_formula_sum 'C32 H33 N3 O2 S' _chemical_formula_weight 523.67 _chemical_melting_point ? _chemical_oxdiff_formula 'C32 H33 N3 O2 S1' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9678(3) _cell_length_b 15.3212(4) _cell_length_c 17.9064(5) _cell_angle_alpha 111.225(3) _cell_angle_beta 98.183(3) _cell_angle_gamma 98.485(3) _cell_volume 2710.90(15) _cell_formula_units_Z 4 _cell_measurement_reflns_used 16273 _cell_measurement_temperature 180.01(10) _cell_measurement_theta_max 73.7010 _cell_measurement_theta_min 3.1300 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 1.327 _exptl_absorpt_correction_T_max 0.942 _exptl_absorpt_correction_T_min 0.719 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description plate _exptl_crystal_F_000 1112 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -5 -2 4 0.0720 5 -3 4 0.1401 4 2 -5 0.0902 -1 1 -1 0.1451 0 -1 -1 0.0230 0 1 1 0.0230 0 1 -1 0.1696 _exptl_crystal_size_max 0.411 _exptl_crystal_size_mid 0.182 _exptl_crystal_size_min 0.046 loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -4.9942 -1.9976 4.0015 -0.1669 0.0479 -0.7587 4.9958 -2.9996 3.9907 0.7621 -0.0989 0.3210 3.9950 1.9982 -4.9995 0.0222 0.0458 0.6808 -0.9992 0.9996 -0.9979 -0.1759 -0.0065 -0.0439 -0.0002 -0.9988 -0.9992 -0.0236 0.1693 -0.0004 0.0002 0.9988 0.9992 0.0236 -0.1693 0.0004 -0.0002 0.9993 -0.9990 -0.0861 -0.0312 0.0674 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_unetI/netI 0.0292 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 42868 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.705 _diffrn_reflns_theta_min 3.169 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 180.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.4679 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 19.00 44.00 1.00 1.00 -- 56.00 80.00 -18.88 25 2 \w 32.00 63.00 1.00 1.00 -- 68.00 77.00 -24.54 31 3 \w 82.00 124.00 1.00 1.00 -- 68.00 77.00 -24.54 42 4 \w 108.00 154.00 1.00 1.00 -- 72.00 76.00 -73.52 46 5 \w 118.00 173.00 1.00 4.00 -- 110.40 111.00-150.00 55 6 \w 110.00 152.00 1.00 4.00 -- 110.40 77.00 -90.00 42 7 \w 109.00 175.00 1.00 4.00 -- 110.40 111.00 0.00 66 8 \w 115.00 178.00 1.00 4.00 -- 110.40 77.00 120.00 63 9 \w 113.00 150.00 1.00 4.00 -- 110.40 77.00 60.00 37 10 \w 108.00 149.00 1.00 1.00 -- 68.00 76.00 169.68 41 11 \w 77.00 108.00 1.00 4.00 -- 110.40 61.00 90.00 31 12 \w 78.00 126.00 1.00 4.00 -- 110.40 61.00 150.00 48 13 \w 79.00 106.00 1.00 4.00 -- 110.40 61.00 120.00 27 14 \w 74.00 100.00 1.00 4.00 -- 110.40 77.00 60.00 26 15 \w 74.00 177.00 1.00 4.00 -- 110.40 77.00 30.00 103 16 \w 80.00 107.00 1.00 4.00 -- 110.40 61.00 -60.00 27 17 \w 74.00 177.00 1.00 4.00 -- 110.40 77.00 -30.00 103 18 \w 78.00 103.00 1.00 4.00 -- 110.40 61.00-180.00 25 19 \w 74.00 176.00 1.00 4.00 -- 110.40 77.00-120.00 102 20 \w 77.00 104.00 1.00 4.00 -- 110.40 61.00 0.00 27 21 \w 78.00 118.00 1.00 4.00 -- 110.40 61.00 -30.00 40 22 \w 74.00 100.00 1.00 4.00 -- 110.40 77.00 -60.00 26 23 \w 74.00 100.00 1.00 4.00 -- 110.40 77.00 -90.00 26 24 \w 74.00 139.00 1.00 4.00 -- 110.40 77.00-150.00 65 25 \w 74.00 177.00 1.00 4.00 -- 110.40 77.00-180.00 103 26 \w 74.00 132.00 1.00 4.00 -- 110.40 77.00 0.00 58 27 \w 74.00 101.00 1.00 4.00 -- 110.40 77.00 120.00 27 28 \w 74.00 178.00 1.00 4.00 -- 110.40 77.00 90.00 104 29 \w 74.00 150.00 1.00 4.00 -- 110.40 77.00 150.00 76 30 \w 55.00 123.00 1.00 1.00 -- 38.94 77.00 150.00 68 31 \w 33.00 62.00 1.00 1.00 -- 68.00 76.00 169.68 29 32 \w 36.00 80.00 1.00 1.00 -- 72.00 77.00 109.24 44 33 \w 36.00 74.00 1.00 1.00 -- 72.00 77.00 70.73 38 34 \w 32.00 60.00 1.00 1.00 -- 68.00 76.00 31.92 28 35 \w 19.00 44.00 1.00 1.00 -- 56.00 80.00 72.06 25 36 \w 19.00 44.00 1.00 1.00 -- 56.00 82.00 19.32 25 37 \w 36.00 67.00 1.00 1.00 -- 72.00 76.00 -73.52 31 38 \w 28.00 54.00 1.00 1.00 -- 64.00 77.00 -92.81 26 39 \w 36.00 140.00 1.00 1.00 -- 72.00 77.00-147.44 104 40 \w 60.00 146.00 1.00 4.00 -- 110.40 178.00-120.00 86 41 \w 19.00 44.00 1.00 1.00 -- 56.00 81.00-152.46 25 42 \w 6.00 34.00 1.00 1.00 -- 44.00 87.00-105.05 28 43 \w -4.00 21.00 1.00 1.00 -- 38.94 96.00 19.65 25 44 \w 4.00 49.00 1.00 1.00 -- 38.94 77.00 150.00 45 45 \w 19.00 45.00 1.00 1.00 -- 56.00 80.00 168.20 26 46 \w -59.00 -8.00 1.00 1.00 -- -38.94 -57.00 150.00 51 47 \w -94.00 -16.00 1.00 1.00 -- -38.94 -38.00 30.00 78 48 \w -71.00 39.00 1.00 1.00 -- -38.94 57.00 -90.00 110 49 \w 35.00 115.00 1.00 4.00 -- 110.40-111.00-150.00 80 50 \w 55.00 130.00 1.00 1.00 -- 38.94-178.00-150.00 75 51 \w 31.00 108.00 1.00 4.00 -- 110.40 -94.00 -60.00 77 52 \w 38.00 113.00 1.00 4.00 -- 110.40-111.00 60.00 75 53 \w -117.00 -74.00 1.00 1.00 -- -38.94 -57.00 150.00 43 54 \w -117.00 -7.00 1.00 1.00 -- -38.94 -57.00 -60.00 110 55 \w -129.00 -57.00 1.00 1.00 -- -38.94 178.00-150.00 72 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0899192000 _diffrn_orient_matrix_UB_12 -0.0312750000 _diffrn_orient_matrix_UB_13 0.0549050000 _diffrn_orient_matrix_UB_21 -0.0248423000 _diffrn_orient_matrix_UB_22 -0.1003657000 _diffrn_orient_matrix_UB_23 -0.0691347000 _diffrn_orient_matrix_UB_31 0.1114378000 _diffrn_orient_matrix_UB_32 0.0339461000 _diffrn_orient_matrix_UB_33 -0.0335616000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 8967 _reflns_number_total 10776 _reflns_odcompleteness_completeness 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 67.29 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _refine_diff_density_max 0.244 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.040 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 698 _refine_ls_number_reflns 10776 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0381 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.5227P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0989 _refine_ls_wR_factor_ref 0.1064 _refine_special_details ; There are two molecules per asymmetric unit. They can be overlaid. (root mean square deviations between the equivalent atoms in the two different molecules is 0.282A) ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C5(H5), C5B(H5B) 2.b Secondary CH2 refined with riding coordinates: C14(H14A,H14B), C15(H15A,H15B), C24(H24A,H24B), C14B(H14C,H14D), C15B(H15C, H15D), C24B(H24C,H24D) 2.c Aromatic/amide H refined with riding coordinates: C7(H7), C10(H10), C11(H11), C18(H18), C19(H19), C22(H22), C23(H23), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33), C34(H34), C37(H37), C38(H38), C7B(H7B), C10B(H10B), C11B(H11B), C18B(H18B), C19B(H19B), C22B(H22B), C23B(H23B), C27B(H27B), C28B(H28B), C29B(H29B), C30B(H30B), C31B(H31B), C33B(H33B), C34B(H34B), C37B(H37B), C38B(H38B) 2.d Idealised Me refined as rotating group: C9(H9A,H9B,H9C), C21(H21A,H21B,H21C), C36(H36A,H36B,H36C), C9B(H9BA,H9BB, H9BC), C21B(H21D,H21E,H21F), C36B(H36D,H36E,H36F) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary ? 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 0.53590(3) 0.15208(3) 0.89892(2) 0.03163(9) Uani 1 1 d . . . . . O2 O 0.57624(12) 0.21612(8) 0.98315(7) 0.0424(3) Uani 1 1 d . . . . . O3 O 0.41119(10) 0.14009(9) 0.85463(9) 0.0459(3) Uani 1 1 d . . . . . N4 N 0.62929(11) 0.18797(9) 0.84831(8) 0.0292(3) Uani 1 1 d . . . . . H4 H 0.600(2) 0.1691(16) 0.7979(14) 0.057(6) Uiso 1 1 d . . . . . N13 N 0.96846(11) 0.24892(9) 0.86124(8) 0.0314(3) Uani 1 1 d . . . . . N16 N 1.00754(11) 0.06930(9) 0.84612(8) 0.0307(3) Uani 1 1 d . . . . . C5 C 0.76313(13) 0.22826(10) 0.88132(8) 0.0269(3) Uani 1 1 d . . . . . H5 H 0.780874 0.235002 0.939724 0.032 Uiso 1 1 calc R . . . . C6 C 0.80707(14) 0.32629(10) 0.88053(9) 0.0297(3) Uani 1 1 d . . . . . C7 C 0.74711(15) 0.40141(11) 0.89113(9) 0.0339(3) Uani 1 1 d . . . . . H7 H 0.661490 0.394103 0.896118 0.041 Uiso 1 1 calc R . . . . C8 C 0.81324(18) 0.48871(12) 0.89451(11) 0.0414(4) Uani 1 1 d . . . . . C9 C 0.7502(2) 0.57268(14) 0.90689(14) 0.0577(5) Uani 1 1 d . . . . . H9A H 0.740620 0.599939 0.963840 0.086 Uiso 1 1 calc GR . . . . H9B H 0.666891 0.550890 0.870014 0.086 Uiso 1 1 calc GR . . . . H9C H 0.802088 0.621665 0.894830 0.086 Uiso 1 1 calc GR . . . . C10 C 0.93841(19) 0.49611(13) 0.88706(12) 0.0480(4) Uani 1 1 d . . . . . H10 H 0.984056 0.555576 0.890336 0.058 Uiso 1 1 calc R . . . . C11 C 1.00023(17) 0.42016(12) 0.87496(12) 0.0429(4) Uani 1 1 d . . . . . H11 H 1.085638 0.426968 0.869510 0.051 Uiso 1 1 calc R . . . . C12 C 0.93195(14) 0.33455(11) 0.87124(9) 0.0324(3) Uani 1 1 d . . . . . C14 C 1.08360(14) 0.22401(12) 0.83856(11) 0.0372(3) Uani 1 1 d . . . . . H14A H 1.152927 0.281808 0.861421 0.045 Uiso 1 1 calc R . . . . H14B H 1.072410 0.196777 0.778137 0.045 Uiso 1 1 calc R . . . . C15 C 1.11511(14) 0.15080(12) 0.87256(11) 0.0387(4) Uani 1 1 d . . . . . H15A H 1.189149 0.127765 0.853208 0.046 Uiso 1 1 calc R . . . . H15B H 1.137115 0.181213 0.933191 0.046 Uiso 1 1 calc R . . . . C17 C 1.03628(13) -0.01341(11) 0.85618(9) 0.0298(3) Uani 1 1 d . . . . . C18 C 1.14104(15) -0.04739(11) 0.82984(10) 0.0348(3) Uani 1 1 d . . . . . H18 H 1.192971 -0.013938 0.806335 0.042 Uiso 1 1 calc R . . . . C19 C 1.16969(15) -0.12912(12) 0.83767(10) 0.0379(3) Uani 1 1 d . . . . . H19 H 1.242102 -0.149851 0.820224 0.046 Uiso 1 1 calc R . . . . C20 C 1.09590(16) -0.18165(11) 0.87020(10) 0.0365(3) Uani 1 1 d . . . . . C21 C 1.12833(19) -0.27046(12) 0.87857(12) 0.0483(4) Uani 1 1 d . . . . . H21A H 1.220159 -0.261338 0.893557 0.072 Uiso 1 1 calc GR . . . . H21B H 1.095640 -0.325552 0.826290 0.072 Uiso 1 1 calc GR . . . . H21C H 1.090244 -0.282174 0.921299 0.072 Uiso 1 1 calc GR . . . . C22 C 0.99221(16) -0.14847(12) 0.89561(10) 0.0383(3) Uani 1 1 d . . . . . H22 H 0.939403 -0.183270 0.917680 0.046 Uiso 1 1 calc R . . . . C23 C 0.96295(15) -0.06551(12) 0.88979(10) 0.0356(3) Uani 1 1 d . . . . . H23 H 0.891952 -0.044077 0.909001 0.043 Uiso 1 1 calc R . . . . C24 C 0.89520(13) 0.09915(10) 0.87296(9) 0.0287(3) Uani 1 1 d . . . . . H24A H 0.912590 0.129334 0.933577 0.034 Uiso 1 1 calc R . . . . H24B H 0.825014 0.042386 0.854511 0.034 Uiso 1 1 calc R . . . . C25 C 0.85731(13) 0.17061(10) 0.83732(9) 0.0269(3) Uani 1 1 d . . . . . C26 C 0.80642(13) 0.12313(11) 0.74405(9) 0.0298(3) Uani 1 1 d . . . . . C27 C 0.83339(15) 0.17145(13) 0.69336(10) 0.0367(3) Uani 1 1 d . . . . . H27 H 0.885726 0.234025 0.716627 0.044 Uiso 1 1 calc R . . . . C28 C 0.78454(18) 0.12900(15) 0.60941(11) 0.0469(4) Uani 1 1 d . . . . . H28 H 0.804339 0.162560 0.575780 0.056 Uiso 1 1 calc R . . . . C29 C 0.70767(19) 0.03868(16) 0.57454(11) 0.0539(5) Uani 1 1 d . . . . . H29 H 0.674914 0.009703 0.517053 0.065 Uiso 1 1 calc R . . . . C30 C 0.67862(19) -0.00940(14) 0.62387(12) 0.0510(5) Uani 1 1 d . . . . . H30 H 0.624803 -0.071418 0.600223 0.061 Uiso 1 1 calc R . . . . C31 C 0.72748(16) 0.03222(12) 0.70779(10) 0.0392(4) Uani 1 1 d . . . . . H31 H 0.706780 -0.001777 0.740939 0.047 Uiso 1 1 calc R . . . . C32 C 0.55796(14) 0.03790(11) 0.89210(9) 0.0312(3) Uani 1 1 d . . . . . C33 C 0.62730(15) 0.02728(12) 0.95789(10) 0.0364(3) Uani 1 1 d . . . . . H33 H 0.662332 0.081377 1.007658 0.044 Uiso 1 1 calc R . . . . C34 C 0.64530(16) -0.06280(13) 0.95073(11) 0.0414(4) Uani 1 1 d . . . . . H34 H 0.692677 -0.069893 0.996104 0.050 Uiso 1 1 calc R . . . . C35 C 0.59554(17) -0.14282(12) 0.87862(12) 0.0420(4) Uani 1 1 d . . . . . C36 C 0.6157(2) -0.24057(15) 0.87106(15) 0.0596(5) Uani 1 1 d . . . . . H36A H 0.658990 -0.236850 0.924282 0.089 Uiso 1 1 calc GR . . . . H36B H 0.667410 -0.262747 0.830454 0.089 Uiso 1 1 calc GR . . . . H36C H 0.533991 -0.285697 0.853526 0.089 Uiso 1 1 calc GR . . . . C37 C 0.52647(18) -0.13055(13) 0.81327(12) 0.0465(4) Uani 1 1 d . . . . . H37 H 0.492210 -0.184535 0.763307 0.056 Uiso 1 1 calc R . . . . C38 C 0.50645(16) -0.04132(12) 0.81935(11) 0.0411(4) Uani 1 1 d . . . . . H38 H 0.458032 -0.034303 0.774282 0.049 Uiso 1 1 calc R . . . . S1B S 0.97983(3) 0.64664(3) 0.40909(3) 0.03648(10) Uani 1 1 d . . . . . O2B O 1.00676(12) 0.71680(8) 0.49114(8) 0.0515(3) Uani 1 1 d . . . . . O3B O 1.07773(11) 0.62792(10) 0.36465(10) 0.0542(4) Uani 1 1 d . . . . . N4B N 0.87984(12) 0.67976(9) 0.35475(9) 0.0320(3) Uani 1 1 d . . . . . H4B H 0.8769(18) 0.6548(14) 0.3066(12) 0.038 Uiso 1 1 d R . . . . N13B N 0.57409(11) 0.74540(9) 0.35554(8) 0.0294(3) Uani 1 1 d . . . . . N16B N 0.44824(12) 0.56854(10) 0.34266(9) 0.0353(3) Uani 1 1 d . . . . . C5B C 0.77897(13) 0.72410(10) 0.38525(9) 0.0273(3) Uani 1 1 d . . . . . H5B H 0.788778 0.735045 0.444536 0.033 Uiso 1 1 calc R . . . . C6B C 0.77929(14) 0.81938(10) 0.37757(8) 0.0281(3) Uani 1 1 d . . . . . C7B C 0.87769(14) 0.89073(10) 0.38576(9) 0.0311(3) Uani 1 1 d . . . . . H7B H 0.962101 0.883943 0.397851 0.037 Uiso 1 1 calc R . . . . C8B C 0.85348(16) 0.97434(11) 0.37622(9) 0.0343(3) Uani 1 1 d . . . . . C9B C 0.96136(18) 1.05111(12) 0.38170(11) 0.0448(4) Uani 1 1 d . . . . . H9BA H 1.025936 1.066281 0.431025 0.067 Uiso 1 1 calc GR . . . . H9BB H 0.930457 1.108823 0.384521 0.067 Uiso 1 1 calc GR . . . . H9BC H 0.997929 1.028195 0.333126 0.067 Uiso 1 1 calc GR . . . . C10B C 0.72861(16) 0.98173(11) 0.36025(9) 0.0363(3) Uani 1 1 d . . . . . H10B H 0.711289 1.038081 0.354262 0.044 Uiso 1 1 calc R . . . . C11B C 0.62719(15) 0.90973(11) 0.35261(9) 0.0340(3) Uani 1 1 d . . . . . H11B H 0.542632 0.916884 0.342202 0.041 Uiso 1 1 calc R . . . . C12B C 0.65420(14) 0.82756(10) 0.36072(8) 0.0279(3) Uani 1 1 d . . . . . C14B C 0.43891(14) 0.71984(12) 0.32641(10) 0.0358(3) Uani 1 1 d . . . . . H14C H 0.417765 0.690296 0.265742 0.043 Uiso 1 1 calc R . . . . H14D H 0.403104 0.777840 0.344677 0.043 Uiso 1 1 calc R . . . . C15B C 0.38424(15) 0.64946(13) 0.36073(12) 0.0408(4) Uani 1 1 d . . . . . H15C H 0.394419 0.682404 0.420795 0.049 Uiso 1 1 calc R . . . . H15D H 0.292937 0.625212 0.336281 0.049 Uiso 1 1 calc R . . . . C17B C 0.38424(14) 0.48313(11) 0.34478(9) 0.0329(3) Uani 1 1 d . . . . . C18B C 0.25751(15) 0.44495(12) 0.30358(10) 0.0377(3) Uani 1 1 d . . . . . H18B H 0.215130 0.478489 0.276474 0.045 Uiso 1 1 calc R . . . . C19B C 0.19376(15) 0.35937(12) 0.30197(10) 0.0407(4) Uani 1 1 d . . . . . H19B H 0.108035 0.335500 0.273755 0.049 Uiso 1 1 calc R . . . . C20B C 0.25088(16) 0.30696(12) 0.34028(10) 0.0401(4) Uani 1 1 d . . . . . C21B C 0.1785(2) 0.21438(14) 0.33892(14) 0.0572(5) Uani 1 1 d . . . . . H21D H 0.101081 0.225206 0.358778 0.086 Uiso 1 1 calc GR . . . . H21E H 0.230698 0.192004 0.374382 0.086 Uiso 1 1 calc GR . . . . H21F H 0.156842 0.165848 0.282703 0.086 Uiso 1 1 calc GR . . . . C22B C 0.37624(17) 0.34461(13) 0.38063(11) 0.0407(4) Uani 1 1 d . . . . . H22B H 0.418407 0.310162 0.406856 0.049 Uiso 1 1 calc R . . . . C23B C 0.44193(15) 0.43111(12) 0.38386(10) 0.0378(3) Uani 1 1 d . . . . . H23B H 0.527164 0.455205 0.413019 0.045 Uiso 1 1 calc R . . . . C24B C 0.58320(14) 0.60078(11) 0.37842(10) 0.0331(3) Uani 1 1 d . . . . . H24C H 0.623367 0.544908 0.367681 0.040 Uiso 1 1 calc R . . . . H24D H 0.597110 0.635933 0.438498 0.040 Uiso 1 1 calc R . . . . C25B C 0.64109(13) 0.66643(10) 0.33984(9) 0.0269(3) Uani 1 1 d . . . . . C26B C 0.63410(13) 0.61146(10) 0.24801(9) 0.0292(3) Uani 1 1 d . . . . . C27B C 0.61695(14) 0.65615(11) 0.19288(9) 0.0330(3) Uani 1 1 d . . . . . H27B H 0.607845 0.720826 0.212406 0.040 Uiso 1 1 calc R . . . . C28B C 0.61299(16) 0.60771(14) 0.11019(10) 0.0421(4) Uani 1 1 d . . . . . H28B H 0.600266 0.639159 0.073631 0.051 Uiso 1 1 calc R . . . . C29B C 0.62743(17) 0.51410(15) 0.08068(11) 0.0493(4) Uani 1 1 d . . . . . H29B H 0.624566 0.481064 0.023971 0.059 Uiso 1 1 calc R . . . . C30B C 0.64603(18) 0.46879(13) 0.13396(13) 0.0518(5) Uani 1 1 d . . . . . H30B H 0.656666 0.404495 0.113958 0.062 Uiso 1 1 calc R . . . . C31B C 0.64930(16) 0.51686(12) 0.21692(11) 0.0410(4) Uani 1 1 d . . . . . H31B H 0.662072 0.484836 0.253021 0.049 Uiso 1 1 calc R . . . . C32B C 0.90481(14) 0.53763(11) 0.41058(9) 0.0319(3) Uani 1 1 d . . . . . C33B C 0.85124(16) 0.53638(12) 0.47552(10) 0.0380(3) Uani 1 1 d . . . . . H33B H 0.855870 0.594476 0.520678 0.046 Uiso 1 1 calc R . . . . C34B C 0.79067(16) 0.44972(13) 0.47430(11) 0.0413(4) Uani 1 1 d . . . . . H34B H 0.753562 0.448994 0.518943 0.050 Uiso 1 1 calc R . . . . C35B C 0.78318(15) 0.36418(12) 0.40928(10) 0.0382(3) Uani 1 1 d . . . . . C36B C 0.71790(19) 0.26982(15) 0.40816(14) 0.0535(5) Uani 1 1 d . . . . . H36D H 0.745060 0.266749 0.461547 0.080 Uiso 1 1 calc GR . . . . H36E H 0.739832 0.217081 0.365318 0.080 Uiso 1 1 calc GR . . . . H36F H 0.626379 0.264295 0.396894 0.080 Uiso 1 1 calc GR . . . . C37B C 0.8401(2) 0.36705(12) 0.34558(11) 0.0488(4) Uani 1 1 d . . . . . H37B H 0.837671 0.308873 0.301092 0.059 Uiso 1 1 calc R . . . . C38B C 0.90034(19) 0.45288(12) 0.34557(11) 0.0444(4) Uani 1 1 d . . . . . H38B H 0.938364 0.453685 0.301285 0.053 Uiso 1 1 calc R . . . . 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 0.02426(17) 0.03364(18) 0.0437(2) 0.01838(15) 0.01528(14) 0.00994(14) O2 0.0491(7) 0.0376(6) 0.0450(6) 0.0138(5) 0.0264(5) 0.0128(5) O3 0.0235(5) 0.0537(7) 0.0743(8) 0.0365(7) 0.0159(5) 0.0140(5) N4 0.0224(6) 0.0345(6) 0.0339(6) 0.0160(5) 0.0079(5) 0.0066(5) N13 0.0222(6) 0.0295(6) 0.0446(7) 0.0162(5) 0.0103(5) 0.0039(5) N16 0.0213(6) 0.0327(6) 0.0432(7) 0.0186(5) 0.0105(5) 0.0079(5) C5 0.0227(7) 0.0296(7) 0.0299(6) 0.0120(5) 0.0080(5) 0.0066(5) C6 0.0304(7) 0.0290(7) 0.0295(7) 0.0105(6) 0.0087(6) 0.0062(6) C7 0.0363(8) 0.0329(7) 0.0334(7) 0.0109(6) 0.0119(6) 0.0112(6) C8 0.0518(10) 0.0310(8) 0.0452(9) 0.0155(7) 0.0166(8) 0.0134(7) C9 0.0786(15) 0.0391(10) 0.0724(13) 0.0283(9) 0.0366(12) 0.0269(10) C10 0.0540(11) 0.0314(8) 0.0622(11) 0.0212(8) 0.0195(9) 0.0054(8) C11 0.0361(9) 0.0355(8) 0.0592(10) 0.0210(8) 0.0152(7) 0.0030(7) C12 0.0304(7) 0.0304(7) 0.0368(7) 0.0136(6) 0.0083(6) 0.0053(6) C14 0.0217(7) 0.0380(8) 0.0568(10) 0.0229(7) 0.0133(6) 0.0051(6) C15 0.0206(7) 0.0400(8) 0.0587(10) 0.0229(8) 0.0087(7) 0.0062(6) C17 0.0254(7) 0.0319(7) 0.0311(7) 0.0116(6) 0.0044(5) 0.0070(6) C18 0.0292(7) 0.0358(8) 0.0415(8) 0.0151(6) 0.0115(6) 0.0093(6) C19 0.0316(8) 0.0355(8) 0.0428(8) 0.0092(7) 0.0072(6) 0.0122(6) C20 0.0382(8) 0.0308(7) 0.0348(7) 0.0092(6) -0.0008(6) 0.0079(6) C21 0.0570(11) 0.0352(9) 0.0513(10) 0.0169(8) 0.0028(8) 0.0145(8) C22 0.0402(9) 0.0385(8) 0.0401(8) 0.0200(7) 0.0093(7) 0.0072(7) C23 0.0313(8) 0.0402(8) 0.0410(8) 0.0192(7) 0.0116(6) 0.0119(6) C24 0.0222(7) 0.0331(7) 0.0353(7) 0.0168(6) 0.0090(5) 0.0077(6) C25 0.0203(6) 0.0296(7) 0.0336(7) 0.0141(6) 0.0095(5) 0.0057(5) C26 0.0240(7) 0.0356(7) 0.0331(7) 0.0129(6) 0.0111(5) 0.0129(6) C27 0.0323(8) 0.0476(9) 0.0386(8) 0.0209(7) 0.0145(6) 0.0166(7) C28 0.0450(10) 0.0700(12) 0.0389(9) 0.0276(9) 0.0176(7) 0.0270(9) C29 0.0538(11) 0.0736(13) 0.0313(8) 0.0118(8) 0.0100(8) 0.0273(10) C30 0.0471(10) 0.0466(10) 0.0432(9) 0.0017(8) 0.0029(8) 0.0101(8) C31 0.0365(8) 0.0390(8) 0.0387(8) 0.0107(7) 0.0094(7) 0.0087(7) C32 0.0245(7) 0.0330(7) 0.0407(8) 0.0177(6) 0.0123(6) 0.0066(6) C33 0.0336(8) 0.0397(8) 0.0390(8) 0.0181(7) 0.0105(6) 0.0074(7) C34 0.0382(9) 0.0496(10) 0.0493(9) 0.0297(8) 0.0150(7) 0.0157(7) C35 0.0384(9) 0.0388(9) 0.0602(10) 0.0257(8) 0.0239(8) 0.0132(7) C36 0.0681(14) 0.0451(11) 0.0853(15) 0.0356(11) 0.0360(12) 0.0253(10) C37 0.0492(10) 0.0347(8) 0.0492(10) 0.0109(7) 0.0099(8) 0.0048(7) C38 0.0374(9) 0.0402(9) 0.0439(9) 0.0177(7) 0.0031(7) 0.0050(7) S1B 0.02329(17) 0.02873(18) 0.0559(2) 0.01606(16) 0.00287(15) 0.00785(14) O2B 0.0453(7) 0.0306(6) 0.0600(8) 0.0074(5) -0.0170(6) 0.0067(5) O3B 0.0274(6) 0.0507(7) 0.1013(11) 0.0414(8) 0.0247(6) 0.0176(5) N4B 0.0249(6) 0.0316(6) 0.0423(7) 0.0151(6) 0.0098(5) 0.0105(5) N13B 0.0238(6) 0.0290(6) 0.0373(6) 0.0128(5) 0.0077(5) 0.0104(5) N16B 0.0216(6) 0.0403(7) 0.0522(8) 0.0255(6) 0.0112(5) 0.0085(5) C5B 0.0223(6) 0.0279(7) 0.0340(7) 0.0137(6) 0.0072(5) 0.0070(5) C6B 0.0294(7) 0.0268(7) 0.0291(6) 0.0106(5) 0.0076(5) 0.0089(6) C7B 0.0313(7) 0.0289(7) 0.0331(7) 0.0106(6) 0.0093(6) 0.0078(6) C8B 0.0428(9) 0.0264(7) 0.0321(7) 0.0092(6) 0.0111(6) 0.0056(6) C9B 0.0520(10) 0.0311(8) 0.0505(10) 0.0164(7) 0.0139(8) 0.0031(7) C10B 0.0491(9) 0.0266(7) 0.0351(7) 0.0120(6) 0.0089(7) 0.0135(7) C11B 0.0366(8) 0.0321(7) 0.0338(7) 0.0112(6) 0.0063(6) 0.0144(6) C12B 0.0282(7) 0.0273(7) 0.0277(6) 0.0088(5) 0.0078(5) 0.0082(6) C14B 0.0239(7) 0.0383(8) 0.0489(9) 0.0181(7) 0.0088(6) 0.0137(6) C15B 0.0264(8) 0.0447(9) 0.0581(10) 0.0229(8) 0.0173(7) 0.0123(7) C17B 0.0273(7) 0.0376(8) 0.0365(7) 0.0158(6) 0.0123(6) 0.0062(6) C18B 0.0275(8) 0.0435(9) 0.0426(8) 0.0174(7) 0.0083(6) 0.0072(7) C19B 0.0286(8) 0.0425(9) 0.0428(8) 0.0093(7) 0.0083(6) 0.0021(7) C20B 0.0397(9) 0.0363(8) 0.0406(8) 0.0109(7) 0.0151(7) 0.0017(7) C21B 0.0559(12) 0.0412(10) 0.0679(13) 0.0190(9) 0.0147(10) -0.0044(9) C22B 0.0399(9) 0.0418(9) 0.0453(9) 0.0224(7) 0.0119(7) 0.0068(7) C23B 0.0297(8) 0.0441(9) 0.0423(8) 0.0216(7) 0.0075(6) 0.0040(7) C24B 0.0232(7) 0.0394(8) 0.0435(8) 0.0229(7) 0.0093(6) 0.0074(6) C25B 0.0210(6) 0.0279(7) 0.0350(7) 0.0143(6) 0.0076(5) 0.0076(5) C26B 0.0198(6) 0.0289(7) 0.0376(7) 0.0108(6) 0.0082(5) 0.0049(5) C27B 0.0248(7) 0.0372(8) 0.0357(7) 0.0135(6) 0.0077(6) 0.0039(6) C28B 0.0315(8) 0.0547(10) 0.0349(8) 0.0134(7) 0.0077(6) 0.0038(7) C29B 0.0360(9) 0.0596(11) 0.0368(8) 0.0023(8) 0.0094(7) 0.0057(8) C30B 0.0431(10) 0.0376(9) 0.0587(11) -0.0008(8) 0.0120(8) 0.0111(8) C31B 0.0381(9) 0.0323(8) 0.0487(9) 0.0102(7) 0.0094(7) 0.0103(7) C32B 0.0276(7) 0.0303(7) 0.0388(8) 0.0132(6) 0.0059(6) 0.0111(6) C33B 0.0417(9) 0.0394(8) 0.0335(7) 0.0111(6) 0.0087(6) 0.0183(7) C34B 0.0396(9) 0.0531(10) 0.0409(8) 0.0247(8) 0.0142(7) 0.0169(8) C35B 0.0325(8) 0.0394(8) 0.0455(9) 0.0224(7) 0.0028(7) 0.0065(7) C36B 0.0431(10) 0.0513(11) 0.0684(12) 0.0354(10) -0.0008(9) -0.0015(8) C37B 0.0681(13) 0.0304(8) 0.0437(9) 0.0089(7) 0.0174(9) 0.0077(8) C38B 0.0597(11) 0.0331(8) 0.0421(9) 0.0108(7) 0.0245(8) 0.0118(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O2 1.4295(13) . ? S1 O3 1.4301(12) . ? S1 N4 1.6224(13) . ? S1 C32 1.7642(15) . ? N4 H4 0.84(2) . ? N4 C5 1.4514(18) . ? N13 C12 1.3852(19) . ? N13 C14 1.4427(19) . ? N13 C25 1.4686(18) . ? N16 C15 1.468(2) . ? N16 C17 1.4159(18) . ? N16 C24 1.4608(17) . ? C5 H5 1.0000 . ? C5 C6 1.514(2) . ? C5 C25 1.5700(18) . ? C6 C7 1.376(2) . ? C6 C12 1.396(2) . ? C7 H7 0.9500 . ? C7 C8 1.400(2) . ? C8 C9 1.511(2) . ? C8 C10 1.390(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10 0.9500 . ? C10 C11 1.397(2) . ? C11 H11 0.9500 . ? C11 C12 1.385(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 C15 1.516(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C17 C18 1.402(2) . ? C17 C23 1.394(2) . ? C18 H18 0.9500 . ? C18 C19 1.385(2) . ? C19 H19 0.9500 . ? C19 C20 1.387(2) . ? C20 C21 1.508(2) . ? C20 C22 1.382(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22 0.9500 . ? C22 C23 1.391(2) . ? C23 H23 0.9500 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C24 C25 1.5308(18) . ? C25 C26 1.5379(19) . ? C26 C27 1.399(2) . ? C26 C31 1.393(2) . ? C27 H27 0.9500 . ? C27 C28 1.389(2) . ? C28 H28 0.9500 . ? C28 C29 1.377(3) . ? C29 H29 0.9500 . ? C29 C30 1.381(3) . ? C30 H30 0.9500 . ? C30 C31 1.388(2) . ? C31 H31 0.9500 . ? C32 C33 1.383(2) . ? C32 C38 1.390(2) . ? C33 H33 0.9500 . ? C33 C34 1.385(2) . ? C34 H34 0.9500 . ? C34 C35 1.387(3) . ? C35 C36 1.507(2) . ? C35 C37 1.389(3) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37 0.9500 . ? C37 C38 1.384(2) . ? C38 H38 0.9500 . ? S1B O2B 1.4284(14) . ? S1B O3B 1.4274(13) . ? S1B N4B 1.6201(13) . ? S1B C32B 1.7608(16) . ? N4B H4B 0.80(2) . ? N4B C5B 1.4522(18) . ? N13B C12B 1.3896(19) . ? N13B C14B 1.4437(18) . ? N13B C25B 1.4690(17) . ? N16B C15B 1.472(2) . ? N16B C17B 1.407(2) . ? N16B C24B 1.4597(19) . ? C5B H5B 1.0000 . ? C5B C6B 1.5146(19) . ? C5B C25B 1.5697(19) . ? C6B C7B 1.368(2) . ? C6B C12B 1.396(2) . ? C7B H7B 0.9500 . ? C7B C8B 1.409(2) . ? C8B C9B 1.505(2) . ? C8B C10B 1.389(2) . ? C9B H9BA 0.9800 . ? C9B H9BB 0.9800 . ? C9B H9BC 0.9800 . ? C10B H10B 0.9500 . ? C10B C11B 1.399(2) . ? C11B H11B 0.9500 . ? C11B C12B 1.387(2) . ? C14B H14C 0.9900 . ? C14B H14D 0.9900 . ? C14B C15B 1.514(2) . ? C15B H15C 0.9900 . ? C15B H15D 0.9900 . ? C17B C18B 1.405(2) . ? C17B C23B 1.397(2) . ? C18B H18B 0.9500 . ? C18B C19B 1.380(2) . ? C19B H19B 0.9500 . ? C19B C20B 1.390(3) . ? C20B C21B 1.510(2) . ? C20B C22B 1.388(2) . ? C21B H21D 0.9800 . ? C21B H21E 0.9800 . ? C21B H21F 0.9800 . ? C22B H22B 0.9500 . ? C22B C23B 1.389(2) . ? C23B H23B 0.9500 . ? C24B H24C 0.9900 . ? C24B H24D 0.9900 . ? C24B C25B 1.527(2) . ? C25B C26B 1.537(2) . ? C26B C27B 1.398(2) . ? C26B C31B 1.397(2) . ? C27B H27B 0.9500 . ? C27B C28B 1.386(2) . ? C28B H28B 0.9500 . ? C28B C29B 1.380(3) . ? C29B H29B 0.9500 . ? C29B C30B 1.378(3) . ? C30B H30B 0.9500 . ? C30B C31B 1.391(3) . ? C31B H31B 0.9500 . ? C32B C33B 1.380(2) . ? C32B C38B 1.384(2) . ? C33B H33B 0.9500 . ? C33B C34B 1.385(2) . ? C34B H34B 0.9500 . ? C34B C35B 1.384(2) . ? C35B C36B 1.507(2) . ? C35B C37B 1.387(3) . ? C36B H36D 0.9800 . ? C36B H36E 0.9800 . ? C36B H36F 0.9800 . ? C37B H37B 0.9500 . ? C37B C38B 1.382(2) . ? C38B H38B 0.9500 . ? 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 O2 S1 O3 120.77(8) . . ? O2 S1 N4 107.55(7) . . ? O2 S1 C32 107.55(7) . . ? O3 S1 N4 105.18(7) . . ? O3 S1 C32 107.68(8) . . ? N4 S1 C32 107.47(7) . . ? S1 N4 H4 114.8(16) . . ? C5 N4 S1 123.01(10) . . ? C5 N4 H4 120.5(16) . . ? C12 N13 C14 126.33(13) . . ? C12 N13 C25 110.41(12) . . ? C14 N13 C25 117.61(12) . . ? C17 N16 C15 115.00(12) . . ? C17 N16 C24 116.79(12) . . ? C24 N16 C15 111.94(12) . . ? N4 C5 H5 107.5 . . ? N4 C5 C6 114.21(12) . . ? N4 C5 C25 117.30(12) . . ? C6 C5 H5 107.5 . . ? C6 C5 C25 102.23(11) . . ? C25 C5 H5 107.5 . . ? C7 C6 C5 130.80(14) . . ? C7 C6 C12 121.33(14) . . ? C12 C6 C5 107.78(12) . . ? C6 C7 H7 120.2 . . ? C6 C7 C8 119.52(15) . . ? C8 C7 H7 120.2 . . ? C7 C8 C9 120.66(17) . . ? C10 C8 C7 118.21(15) . . ? C10 C8 C9 121.13(17) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10 118.5 . . ? C8 C10 C11 123.07(16) . . ? C11 C10 H10 118.5 . . ? C10 C11 H11 121.3 . . ? C12 C11 C10 117.31(16) . . ? C12 C11 H11 121.3 . . ? N13 C12 C6 109.44(13) . . ? N13 C12 C11 130.00(15) . . ? C11 C12 C6 120.53(14) . . ? N13 C14 H14A 110.1 . . ? N13 C14 H14B 110.1 . . ? N13 C14 C15 108.00(13) . . ? H14A C14 H14B 108.4 . . ? C15 C14 H14A 110.1 . . ? C15 C14 H14B 110.1 . . ? N16 C15 C14 110.57(13) . . ? N16 C15 H15A 109.5 . . ? N16 C15 H15B 109.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C18 C17 N16 119.75(14) . . ? C23 C17 N16 123.01(13) . . ? C23 C17 C18 117.22(14) . . ? C17 C18 H18 119.6 . . ? C19 C18 C17 120.79(15) . . ? C19 C18 H18 119.6 . . ? C18 C19 H19 119.0 . . ? C18 C19 C20 122.02(15) . . ? C20 C19 H19 119.0 . . ? C19 C20 C21 121.49(16) . . ? C22 C20 C19 117.13(15) . . ? C22 C20 C21 121.38(16) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22 119.1 . . ? C20 C22 C23 121.86(16) . . ? C23 C22 H22 119.1 . . ? C17 C23 H23 119.5 . . ? C22 C23 C17 120.96(15) . . ? C22 C23 H23 119.5 . . ? N16 C24 H24A 109.7 . . ? N16 C24 H24B 109.7 . . ? N16 C24 C25 110.00(11) . . ? H24A C24 H24B 108.2 . . ? C25 C24 H24A 109.7 . . ? C25 C24 H24B 109.7 . . ? N13 C25 C5 99.77(11) . . ? N13 C25 C24 106.91(11) . . ? N13 C25 C26 112.84(12) . . ? C24 C25 C5 113.52(11) . . ? C24 C25 C26 112.25(12) . . ? C26 C25 C5 110.90(11) . . ? C27 C26 C25 121.11(14) . . ? C31 C26 C25 120.98(14) . . ? C31 C26 C27 117.85(15) . . ? C26 C27 H27 119.6 . . ? C28 C27 C26 120.78(17) . . ? C28 C27 H27 119.6 . . ? C27 C28 H28 119.7 . . ? C29 C28 C27 120.54(17) . . ? C29 C28 H28 119.7 . . ? C28 C29 H29 120.3 . . ? C28 C29 C30 119.41(17) . . ? C30 C29 H29 120.3 . . ? C29 C30 H30 119.8 . . ? C29 C30 C31 120.49(19) . . ? C31 C30 H30 119.8 . . ? C26 C31 H31 119.5 . . ? C30 C31 C26 120.92(17) . . ? C30 C31 H31 119.5 . . ? C33 C32 S1 120.50(12) . . ? C33 C32 C38 120.21(15) . . ? C38 C32 S1 119.29(12) . . ? C32 C33 H33 120.2 . . ? C32 C33 C34 119.55(16) . . ? C34 C33 H33 120.2 . . ? C33 C34 H34 119.3 . . ? C33 C34 C35 121.32(16) . . ? C35 C34 H34 119.3 . . ? C34 C35 C36 121.11(18) . . ? C34 C35 C37 118.20(16) . . ? C37 C35 C36 120.69(18) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36B 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37 119.3 . . ? C38 C37 C35 121.41(17) . . ? C38 C37 H37 119.3 . . ? C32 C38 H38 120.3 . . ? C37 C38 C32 119.30(16) . . ? C37 C38 H38 120.3 . . ? O2B S1B N4B 107.02(7) . . ? O2B S1B C32B 107.28(8) . . ? O3B S1B O2B 120.89(9) . . ? O3B S1B N4B 105.19(8) . . ? O3B S1B C32B 107.88(7) . . ? N4B S1B C32B 108.03(7) . . ? S1B N4B H4B 113.0(14) . . ? C5B N4B S1B 123.26(11) . . ? C5B N4B H4B 121.1(14) . . ? C12B N13B C14B 126.12(12) . . ? C12B N13B C25B 109.72(11) . . ? C14B N13B C25B 117.04(12) . . ? C17B N16B C15B 117.39(12) . . ? C17B N16B C24B 118.23(12) . . ? C24B N16B C15B 111.54(13) . . ? N4B C5B H5B 108.3 . . ? N4B C5B C6B 113.41(12) . . ? N4B C5B C25B 116.03(12) . . ? C6B C5B H5B 108.3 . . ? C6B C5B C25B 102.16(11) . . ? C25B C5B H5B 108.3 . . ? C7B C6B C5B 130.45(13) . . ? C7B C6B C12B 121.53(13) . . ? C12B C6B C5B 108.01(12) . . ? C6B C7B H7B 120.1 . . ? C6B C7B C8B 119.82(14) . . ? C8B C7B H7B 120.1 . . ? C7B C8B C9B 119.91(15) . . ? C10B C8B C7B 117.92(15) . . ? C10B C8B C9B 122.16(14) . . ? C8B C9B H9BA 109.5 . . ? C8B C9B H9BB 109.5 . . ? C8B C9B H9BC 109.5 . . ? H9BA C9B H9BB 109.5 . . ? H9BA C9B H9BC 109.5 . . ? H9BB C9B H9BC 109.5 . . ? C8B C10B H10B 118.6 . . ? C8B C10B C11B 122.80(14) . . ? C11B C10B H10B 118.6 . . ? C10B C11B H11B 121.1 . . ? C12B C11B C10B 117.81(14) . . ? C12B C11B H11B 121.1 . . ? N13B C12B C6B 109.52(12) . . ? C11B C12B N13B 130.38(14) . . ? C11B C12B C6B 120.10(14) . . ? N13B C14B H14C 110.0 . . ? N13B C14B H14D 110.0 . . ? N13B C14B C15B 108.37(13) . . ? H14C C14B H14D 108.4 . . ? C15B C14B H14C 110.0 . . ? C15B C14B H14D 110.0 . . ? N16B C15B C14B 110.47(13) . . ? N16B C15B H15C 109.6 . . ? N16B C15B H15D 109.6 . . ? C14B C15B H15C 109.6 . . ? C14B C15B H15D 109.6 . . ? H15C C15B H15D 108.1 . . ? C18B C17B N16B 119.60(14) . . ? C23B C17B N16B 123.13(14) . . ? C23B C17B C18B 117.23(15) . . ? C17B C18B H18B 119.6 . . ? C19B C18B C17B 120.88(15) . . ? C19B C18B H18B 119.6 . . ? C18B C19B H19B 118.9 . . ? C18B C19B C20B 122.16(16) . . ? C20B C19B H19B 118.9 . . ? C19B C20B C21B 121.19(17) . . ? C22B C20B C19B 116.85(16) . . ? C22B C20B C21B 121.95(17) . . ? C20B C21B H21D 109.5 . . ? C20B C21B H21E 109.5 . . ? C20B C21B H21F 109.5 . . ? H21D C21B H21E 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? C20B C22B H22B 119.0 . . ? C20B C22B C23B 122.02(16) . . ? C23B C22B H22B 119.0 . . ? C17B C23B H23B 119.6 . . ? C22B C23B C17B 120.84(15) . . ? C22B C23B H23B 119.6 . . ? N16B C24B H24C 110.0 . . ? N16B C24B H24D 110.0 . . ? N16B C24B C25B 108.48(12) . . ? H24C C24B H24D 108.4 . . ? C25B C24B H24C 110.0 . . ? C25B C24B H24D 110.0 . . ? N13B C25B C5B 100.22(11) . . ? N13B C25B C24B 106.97(11) . . ? N13B C25B C26B 112.54(11) . . ? C24B C25B C5B 114.14(11) . . ? C24B C25B C26B 111.50(12) . . ? C26B C25B C5B 110.95(11) . . ? C27B C26B C25B 120.73(13) . . ? C31B C26B C25B 121.69(14) . . ? C31B C26B C27B 117.53(15) . . ? C26B C27B H27B 119.4 . . ? C28B C27B C26B 121.13(15) . . ? C28B C27B H27B 119.4 . . ? C27B C28B H28B 119.8 . . ? C29B C28B C27B 120.39(17) . . ? C29B C28B H28B 119.8 . . ? C28B C29B H29B 120.2 . . ? C30B C29B C28B 119.62(16) . . ? C30B C29B H29B 120.2 . . ? C29B C30B H30B 119.9 . . ? C29B C30B C31B 120.24(17) . . ? C31B C30B H30B 119.9 . . ? C26B C31B H31B 119.5 . . ? C30B C31B C26B 121.09(17) . . ? C30B C31B H31B 119.5 . . ? C33B C32B S1B 120.70(12) . . ? C33B C32B C38B 120.31(16) . . ? C38B C32B S1B 118.99(13) . . ? C32B C33B H33B 120.3 . . ? C32B C33B C34B 119.45(15) . . ? C34B C33B H33B 120.3 . . ? C33B C34B H34B 119.4 . . ? C35B C34B C33B 121.26(16) . . ? C35B C34B H34B 119.4 . . ? C34B C35B C36B 121.27(17) . . ? C34B C35B C37B 118.22(16) . . ? C37B C35B C36B 120.49(17) . . ? C35B C36B H36D 109.5 . . ? C35B C36B H36E 109.5 . . ? C35B C36B H36F 109.5 . . ? H36D C36B H36E 109.5 . . ? H36D C36B H36F 109.5 . . ? H36E C36B H36F 109.5 . . ? C35B C37B H37B 119.4 . . ? C38B C37B C35B 121.29(16) . . ? C38B C37B H37B 119.4 . . ? C32B C38B H38B 120.3 . . ? C37B C38B C32B 119.45(16) . . ? C37B C38B H38B 120.3 . . ? _shelx_res_file ; TITL ajgi-665-23_a.res in P-1 ajgi-665-23.res created by SHELXL-2017/1 at 14:50:10 on 11-Jul-2017 REM Old TITL REM SHELXT solution in P-1 REM R1 0.157, Rweak 0.007, Alpha 0.084, Orientation as input REM Formula found by SHELXT: C62 N6 O6 S2 CELL 1.54184 10.967774 15.321158 17.90639 111.2252 98.1833 98.4846 ZERR 4 0.000329 0.000449 0.000536 0.0027 0.0025 0.0025 LATT 1 SFAC C H N O S UNIT 128 132 12 8 4 L.S. 4 PLAN 20 TEMP -93 BOND $H list 4 fmap 2 acta REM REM REM WGHT 0.055500 0.522700 FVAR 4.37297 S1 5 0.535903 0.152078 0.898923 11.00000 0.02426 0.03364 = 0.04369 0.01838 0.01528 0.00994 O2 4 0.576240 0.216117 0.983146 11.00000 0.04907 0.03762 = 0.04496 0.01381 0.02641 0.01277 O3 4 0.411193 0.140095 0.854627 11.00000 0.02354 0.05366 = 0.07428 0.03651 0.01593 0.01401 N4 3 0.629293 0.187974 0.848305 11.00000 0.02238 0.03447 = 0.03390 0.01599 0.00791 0.00655 H4 2 0.599672 0.169064 0.797914 11.00000 0.05658 N13 3 0.968462 0.248919 0.861239 11.00000 0.02216 0.02946 = 0.04464 0.01616 0.01028 0.00394 N16 3 1.007537 0.069299 0.846116 11.00000 0.02129 0.03271 = 0.04318 0.01859 0.01052 0.00788 C5 1 0.763131 0.228259 0.881324 11.00000 0.02270 0.02959 = 0.02988 0.01203 0.00797 0.00662 AFIX 13 H5 2 0.780874 0.235002 0.939724 11.00000 -1.20000 AFIX 0 C6 1 0.807073 0.326287 0.880532 11.00000 0.03035 0.02899 = 0.02949 0.01048 0.00866 0.00617 C7 1 0.747113 0.401412 0.891131 11.00000 0.03627 0.03293 = 0.03340 0.01092 0.01187 0.01125 AFIX 43 H7 2 0.661490 0.394103 0.896118 11.00000 -1.20000 AFIX 0 C8 1 0.813237 0.488711 0.894513 11.00000 0.05184 0.03104 = 0.04523 0.01547 0.01662 0.01344 C9 1 0.750170 0.572676 0.906886 11.00000 0.07861 0.03909 = 0.07240 0.02832 0.03662 0.02693 AFIX 137 H9A 2 0.740620 0.599939 0.963840 11.00000 -1.50000 H9B 2 0.666891 0.550890 0.870014 11.00000 -1.50000 H9C 2 0.802088 0.621665 0.894830 11.00000 -1.50000 AFIX 0 C10 1 0.938409 0.496108 0.887056 11.00000 0.05404 0.03145 = 0.06218 0.02118 0.01951 0.00537 AFIX 43 H10 2 0.984056 0.555576 0.890336 11.00000 -1.20000 AFIX 0 C11 1 1.000227 0.420156 0.874961 11.00000 0.03611 0.03552 = 0.05920 0.02100 0.01517 0.00300 AFIX 43 H11 2 1.085638 0.426968 0.869510 11.00000 -1.20000 AFIX 0 C12 1 0.931946 0.334545 0.871240 11.00000 0.03040 0.03042 = 0.03680 0.01356 0.00826 0.00535 C14 1 1.083605 0.224008 0.838564 11.00000 0.02175 0.03804 = 0.05683 0.02294 0.01328 0.00506 AFIX 23 H14A 2 1.152927 0.281808 0.861421 11.00000 -1.20000 H14B 2 1.072410 0.196777 0.778137 11.00000 -1.20000 AFIX 0 C15 1 1.115111 0.150799 0.872557 11.00000 0.02058 0.04000 = 0.05875 0.02293 0.00874 0.00625 AFIX 23 H15A 2 1.189149 0.127765 0.853208 11.00000 -1.20000 H15B 2 1.137115 0.181213 0.933191 11.00000 -1.20000 AFIX 0 C17 1 1.036283 -0.013409 0.856182 11.00000 0.02541 0.03190 = 0.03111 0.01162 0.00438 0.00699 C18 1 1.141041 -0.047394 0.829836 11.00000 0.02916 0.03575 = 0.04152 0.01512 0.01154 0.00933 AFIX 43 H18 2 1.192971 -0.013938 0.806335 11.00000 -1.20000 AFIX 0 C19 1 1.169685 -0.129121 0.837668 11.00000 0.03155 0.03554 = 0.04281 0.00917 0.00722 0.01223 AFIX 43 H19 2 1.242102 -0.149851 0.820224 11.00000 -1.20000 AFIX 0 C20 1 1.095898 -0.181652 0.870200 11.00000 0.03821 0.03078 = 0.03484 0.00919 -0.00076 0.00789 C21 1 1.128325 -0.270456 0.878569 11.00000 0.05702 0.03524 = 0.05126 0.01686 0.00277 0.01445 AFIX 137 H21A 2 1.220159 -0.261338 0.893557 11.00000 -1.50000 H21B 2 1.095640 -0.325552 0.826290 11.00000 -1.50000 H21C 2 1.090244 -0.282174 0.921299 11.00000 -1.50000 AFIX 0 C22 1 0.992206 -0.148465 0.895611 11.00000 0.04022 0.03848 = 0.04013 0.01995 0.00928 0.00716 AFIX 43 H22 2 0.939403 -0.183270 0.917680 11.00000 -1.20000 AFIX 0 C23 1 0.962950 -0.065514 0.889789 11.00000 0.03134 0.04016 = 0.04099 0.01924 0.01160 0.01189 AFIX 43 H23 2 0.891952 -0.044077 0.909001 11.00000 -1.20000 AFIX 0 C24 1 0.895202 0.099149 0.872957 11.00000 0.02222 0.03314 = 0.03532 0.01683 0.00897 0.00774 AFIX 23 H24A 2 0.912590 0.129334 0.933577 11.00000 -1.20000 H24B 2 0.825014 0.042386 0.854511 11.00000 -1.20000 AFIX 0 C25 1 0.857310 0.170611 0.837322 11.00000 0.02026 0.02960 = 0.03360 0.01411 0.00952 0.00571 C26 1 0.806425 0.123134 0.744054 11.00000 0.02401 0.03555 = 0.03307 0.01292 0.01110 0.01288 C27 1 0.833392 0.171450 0.693359 11.00000 0.03228 0.04763 = 0.03858 0.02087 0.01450 0.01659 AFIX 43 H27 2 0.885726 0.234025 0.716627 11.00000 -1.20000 AFIX 0 C28 1 0.784544 0.129000 0.609406 11.00000 0.04498 0.07004 = 0.03888 0.02757 0.01763 0.02705 AFIX 43 H28 2 0.804339 0.162560 0.575780 11.00000 -1.20000 AFIX 0 C29 1 0.707672 0.038680 0.574538 11.00000 0.05381 0.07363 = 0.03133 0.01178 0.00998 0.02727 AFIX 43 H29 2 0.674914 0.009703 0.517053 11.00000 -1.20000 AFIX 0 C30 1 0.678618 -0.009403 0.623873 11.00000 0.04711 0.04655 = 0.04323 0.00165 0.00288 0.01007 AFIX 43 H30 2 0.624803 -0.071418 0.600223 11.00000 -1.20000 AFIX 0 C31 1 0.727477 0.032218 0.707789 11.00000 0.03652 0.03903 = 0.03874 0.01074 0.00943 0.00867 AFIX 43 H31 2 0.706780 -0.001777 0.740939 11.00000 -1.20000 AFIX 0 C32 1 0.557961 0.037898 0.892096 11.00000 0.02453 0.03303 = 0.04074 0.01767 0.01226 0.00656 C33 1 0.627297 0.027276 0.957893 11.00000 0.03359 0.03970 = 0.03902 0.01809 0.01054 0.00739 AFIX 43 H33 2 0.662332 0.081377 1.007658 11.00000 -1.20000 AFIX 0 C34 1 0.645302 -0.062797 0.950726 11.00000 0.03824 0.04956 = 0.04925 0.02969 0.01498 0.01572 AFIX 43 H34 2 0.692677 -0.069893 0.996104 11.00000 -1.20000 AFIX 0 C35 1 0.595544 -0.142824 0.878624 11.00000 0.03835 0.03885 = 0.06020 0.02567 0.02392 0.01323 C36 1 0.615749 -0.240571 0.871060 11.00000 0.06807 0.04507 = 0.08526 0.03557 0.03597 0.02534 AFIX 137 H36A 2 0.658990 -0.236850 0.924282 11.00000 -1.50000 H36B 2 0.667410 -0.262747 0.830454 11.00000 -1.50000 H36C 2 0.533991 -0.285697 0.853526 11.00000 -1.50000 AFIX 0 C37 1 0.526469 -0.130547 0.813268 11.00000 0.04917 0.03469 = 0.04923 0.01089 0.00988 0.00481 AFIX 43 H37 2 0.492210 -0.184535 0.763307 11.00000 -1.20000 AFIX 0 C38 1 0.506454 -0.041323 0.819348 11.00000 0.03743 0.04022 = 0.04393 0.01771 0.00315 0.00498 AFIX 43 H38 2 0.458032 -0.034303 0.774282 11.00000 -1.20000 AFIX 0 S1B 5 0.979826 0.646645 0.409094 11.00000 0.02329 0.02873 = 0.05594 0.01606 0.00287 0.00785 O2B 4 1.006759 0.716802 0.491140 11.00000 0.04532 0.03064 = 0.06002 0.00742 -0.01701 0.00671 O3B 4 1.077731 0.627924 0.364651 11.00000 0.02738 0.05075 = 0.10131 0.04137 0.02471 0.01757 N4B 3 0.879838 0.679760 0.354755 11.00000 0.02489 0.03158 = 0.04232 0.01506 0.00979 0.01052 H4B 2 0.876942 0.654845 0.306559 11.00000 -1.20000 N13B 3 0.574091 0.745402 0.355537 11.00000 0.02380 0.02898 = 0.03734 0.01285 0.00772 0.01041 N16B 3 0.448237 0.568544 0.342658 11.00000 0.02162 0.04029 = 0.05221 0.02555 0.01124 0.00850 C5B 1 0.778968 0.724101 0.385248 11.00000 0.02234 0.02791 = 0.03403 0.01371 0.00720 0.00704 AFIX 13 H5B 2 0.788778 0.735045 0.444536 11.00000 -1.20000 AFIX 0 C6B 1 0.779292 0.819379 0.377566 11.00000 0.02940 0.02677 = 0.02912 0.01056 0.00757 0.00893 C7B 1 0.877689 0.890734 0.385760 11.00000 0.03125 0.02889 = 0.03308 0.01055 0.00930 0.00778 AFIX 43 H7B 2 0.962101 0.883943 0.397851 11.00000 -1.20000 AFIX 0 C8B 1 0.853481 0.974341 0.376216 11.00000 0.04280 0.02639 = 0.03213 0.00924 0.01115 0.00558 C9B 1 0.961361 1.051106 0.381700 11.00000 0.05204 0.03108 = 0.05054 0.01637 0.01395 0.00307 AFIX 137 H9BA 2 1.025936 1.066281 0.431025 11.00000 -1.50000 H9BB 2 0.930457 1.108823 0.384521 11.00000 -1.50000 H9BC 2 0.997929 1.028195 0.333126 11.00000 -1.50000 AFIX 0 C10B 1 0.728613 0.981735 0.360252 11.00000 0.04909 0.02657 = 0.03510 0.01202 0.00890 0.01349 AFIX 43 H10B 2 0.711289 1.038081 0.354262 11.00000 -1.20000 AFIX 0 C11B 1 0.627192 0.909727 0.352607 11.00000 0.03661 0.03208 = 0.03381 0.01122 0.00630 0.01437 AFIX 43 H11B 2 0.542632 0.916884 0.342202 11.00000 -1.20000 AFIX 0 C12B 1 0.654203 0.827559 0.360723 11.00000 0.02824 0.02733 = 0.02767 0.00877 0.00779 0.00824 C14B 1 0.438911 0.719835 0.326411 11.00000 0.02391 0.03830 = 0.04891 0.01815 0.00879 0.01374 AFIX 23 H14C 2 0.417765 0.690296 0.265742 11.00000 -1.20000 H14D 2 0.403104 0.777840 0.344677 11.00000 -1.20000 AFIX 0 C15B 1 0.384239 0.649464 0.360730 11.00000 0.02636 0.04470 = 0.05812 0.02286 0.01732 0.01228 AFIX 23 H15C 2 0.394419 0.682404 0.420795 11.00000 -1.20000 H15D 2 0.292937 0.625212 0.336281 11.00000 -1.20000 AFIX 0 C17B 1 0.384240 0.483125 0.344779 11.00000 0.02728 0.03761 = 0.03649 0.01579 0.01230 0.00622 C18B 1 0.257508 0.444951 0.303581 11.00000 0.02753 0.04352 = 0.04262 0.01735 0.00832 0.00718 AFIX 43 H18B 2 0.215130 0.478489 0.276474 11.00000 -1.20000 AFIX 0 C19B 1 0.193760 0.359372 0.301968 11.00000 0.02858 0.04251 = 0.04283 0.00926 0.00831 0.00209 AFIX 43 H19B 2 0.108035 0.335500 0.273755 11.00000 -1.20000 AFIX 0 C20B 1 0.250884 0.306961 0.340276 11.00000 0.03967 0.03627 = 0.04058 0.01092 0.01507 0.00167 C21B 1 0.178529 0.214383 0.338915 11.00000 0.05585 0.04122 = 0.06786 0.01898 0.01470 -0.00437 AFIX 137 H21D 2 0.101081 0.225206 0.358778 11.00000 -1.50000 H21E 2 0.230698 0.192004 0.374382 11.00000 -1.50000 H21F 2 0.156842 0.165848 0.282703 11.00000 -1.50000 AFIX 0 C22B 1 0.376237 0.344608 0.380635 11.00000 0.03990 0.04184 = 0.04528 0.02239 0.01190 0.00678 AFIX 43 H22B 2 0.418407 0.310162 0.406856 11.00000 -1.20000 AFIX 0 C23B 1 0.441926 0.431112 0.383862 11.00000 0.02966 0.04414 = 0.04227 0.02159 0.00754 0.00400 AFIX 43 H23B 2 0.527164 0.455205 0.413019 11.00000 -1.20000 AFIX 0 C24B 1 0.583201 0.600783 0.378422 11.00000 0.02319 0.03944 = 0.04349 0.02290 0.00927 0.00743 AFIX 23 H24C 2 0.623367 0.544908 0.367681 11.00000 -1.20000 H24D 2 0.597110 0.635933 0.438498 11.00000 -1.20000 AFIX 0 C25B 1 0.641092 0.666425 0.339845 11.00000 0.02104 0.02788 = 0.03499 0.01429 0.00762 0.00764 C26B 1 0.634102 0.611463 0.248014 11.00000 0.01983 0.02892 = 0.03756 0.01076 0.00820 0.00494 C27B 1 0.616949 0.656147 0.192878 11.00000 0.02480 0.03719 = 0.03574 0.01346 0.00769 0.00391 AFIX 43 H27B 2 0.607845 0.720826 0.212406 11.00000 -1.20000 AFIX 0 C28B 1 0.612993 0.607712 0.110193 11.00000 0.03149 0.05473 = 0.03490 0.01345 0.00768 0.00383 AFIX 43 H28B 2 0.600266 0.639159 0.073631 11.00000 -1.20000 AFIX 0 C29B 1 0.627431 0.514099 0.080684 11.00000 0.03598 0.05957 = 0.03677 0.00227 0.00936 0.00574 AFIX 43 H29B 2 0.624566 0.481064 0.023971 11.00000 -1.20000 AFIX 0 C30B 1 0.646034 0.468788 0.133959 11.00000 0.04308 0.03761 = 0.05875 -0.00076 0.01204 0.01105 AFIX 43 H30B 2 0.656666 0.404495 0.113958 11.00000 -1.20000 AFIX 0 C31B 1 0.649299 0.516862 0.216918 11.00000 0.03813 0.03227 = 0.04872 0.01024 0.00941 0.01035 AFIX 43 H31B 2 0.662072 0.484836 0.253021 11.00000 -1.20000 AFIX 0 C32B 1 0.904811 0.537626 0.410585 11.00000 0.02762 0.03031 = 0.03878 0.01321 0.00593 0.01113 C33B 1 0.851245 0.536385 0.475518 11.00000 0.04174 0.03937 = 0.03348 0.01106 0.00875 0.01834 AFIX 43 H33B 2 0.855870 0.594476 0.520678 11.00000 -1.20000 AFIX 0 C34B 1 0.790670 0.449724 0.474301 11.00000 0.03964 0.05314 = 0.04086 0.02472 0.01420 0.01686 AFIX 43 H34B 2 0.753562 0.448994 0.518943 11.00000 -1.20000 AFIX 0 C35B 1 0.783181 0.364182 0.409283 11.00000 0.03255 0.03941 = 0.04546 0.02244 0.00278 0.00646 C36B 1 0.717903 0.269822 0.408162 11.00000 0.04305 0.05133 = 0.06843 0.03538 -0.00079 -0.00147 AFIX 137 H36D 2 0.745060 0.266749 0.461547 11.00000 -1.50000 H36E 2 0.739832 0.217081 0.365318 11.00000 -1.50000 H36F 2 0.626379 0.264295 0.396894 11.00000 -1.50000 AFIX 0 C37B 1 0.840124 0.367051 0.345579 11.00000 0.06807 0.03043 = 0.04372 0.00890 0.01744 0.00767 AFIX 43 H37B 2 0.837671 0.308873 0.301092 11.00000 -1.20000 AFIX 0 C38B 1 0.900345 0.452876 0.345567 11.00000 0.05967 0.03313 = 0.04206 0.01082 0.02448 0.01181 AFIX 43 H38B 2 0.938364 0.453685 0.301285 11.00000 -1.20000 AFIX 0 HKLF 4 REM ajgi-665-23_a.res in P-1 REM R1 = 0.0381 for 8967 Fo > 4sig(Fo) and 0.0480 for all 10776 data REM 698 parameters refined using 0 restraints END WGHT 0.0555 0.5227 REM Highest difference peak 0.244, deepest hole -0.419, 1-sigma level 0.040 Q1 1 0.7230 0.8274 0.3701 11.00000 0.05 0.24 Q2 1 0.7874 0.7754 0.3809 11.00000 0.05 0.24 Q3 1 0.5730 -0.2575 0.9116 11.00000 0.05 0.24 Q4 1 0.6555 0.5589 0.9247 11.00000 0.05 0.23 Q5 1 0.7905 0.2265 0.4229 11.00000 0.05 0.22 Q6 1 0.0835 0.1969 0.2994 11.00000 0.05 0.22 Q7 1 0.9375 0.5821 0.4105 11.00000 0.05 0.22 Q8 1 0.7791 0.2813 0.8808 11.00000 0.05 0.21 Q9 1 0.8086 0.1973 0.8582 11.00000 0.05 0.21 Q10 1 0.7966 0.9837 0.3854 11.00000 0.05 0.21 Q11 1 0.5782 -0.2917 0.8091 11.00000 0.05 0.20 Q12 1 0.8766 0.1390 0.8583 11.00000 0.05 0.19 Q13 1 0.9823 1.1161 0.4299 11.00000 0.05 0.18 Q14 1 0.7061 0.6876 0.3626 11.00000 0.05 0.18 Q15 1 0.6033 0.7081 0.3523 11.00000 0.05 0.18 Q16 1 1.1807 -0.2591 0.9278 11.00000 0.05 0.18 Q17 1 0.6187 0.6351 0.3561 11.00000 0.05 0.18 Q18 1 0.8644 0.9317 0.3729 11.00000 0.05 0.18 Q19 1 0.8756 0.4999 0.3690 11.00000 0.05 0.17 Q20 1 0.5478 0.0843 0.8995 11.00000 0.05 0.17 ; _shelx_res_checksum 34469 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.338 _oxdiff_exptl_absorpt_empirical_full_min 0.695 ####################################################################### # # 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_ajgi879b _database_code_depnum_ccdc_archive 'CCDC 2015204' loop_ _audit_author_name _audit_author_address 'Celine Besnard' ;university of Geneva Switzerland ; _audit_update_record ; 2020-07-09 deposited with the CCDC. 2020-11-23 downloaded from the CCDC. ; _audit_creation_date 2019-12-05 _audit_creation_method ; Olex2 1.3 (compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938) ; _shelx_SHELXL_version_number 2018/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C26 H25 N3 O2' _chemical_formula_sum 'C26 H25 N3 O2' _chemical_formula_weight 411.49 _chemical_absolute_configuration ? _chemical_melting_point ? _chemical_oxdiff_formula 'C26 H25 N3 O2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system orthorhombic _space_group_IT_number 45 _space_group_name_H-M_alt 'I b a 2' _space_group_name_Hall 'I 2 -2c' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, z+1/2' _cell_length_a 18.50216(12) _cell_length_b 21.27952(14) _cell_length_c 10.92519(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4301.43(5) _cell_formula_units_Z 8 _cell_measurement_reflns_used 53948 _cell_measurement_temperature 149.99(10) _cell_measurement_theta_max 74.2240 _cell_measurement_theta_min 3.1410 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 0.647 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.408 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description plate _exptl_crystal_F_000 1744 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 -1 0 0.0409 1 1 0 0.0085 1 0 -1 0.2544 1 1 2 0.2818 -1 1 0 0.0559 1 -1 0 0.0481 _exptl_crystal_size_max 0.652 _exptl_crystal_size_mid 0.112 _exptl_crystal_size_min 0.049 loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.9995 -1.0001 0.0000 -0.0166 -0.1011 0.0407 0.9995 1.0001 -0.0000 0.0166 0.1011 -0.0407 0.9998 -0.0005 -0.9999 -0.0594 0.1174 0.0975 0.9989 1.0012 1.9997 0.0467 -0.0079 -0.2991 -0.9996 1.0001 -0.0000 0.1051 -0.0247 0.0226 0.9996 -1.0001 0.0000 -0.1051 0.0247 -0.0226 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_unetI/netI 0.0090 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 89610 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.897 _diffrn_reflns_theta_min 3.165 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 149.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix-Arc _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -91.00 -66.00 0.50 1.00 -- -57.24 154.00-128.00 50 2 \w -53.00 -20.00 0.50 1.00 -- -57.24 93.00-179.00 66 3 \w -51.00 -13.00 0.50 1.00 -- -57.24 120.00 74.00 76 4 \w -106.00 -62.00 0.50 1.00 -- -57.24 -31.00-154.00 88 5 \w -33.00 -8.00 0.50 1.00 -- -57.24 31.00 5.00 50 6 \w 24.00 49.00 0.50 1.00 -- 60.61 -93.00 68.00 50 7 \w 63.00 88.00 0.50 1.00 -- 60.61 31.00 5.00 50 8 \w 55.00 80.00 0.50 1.00 -- 60.61-154.00-167.00 50 9 \w 36.00 61.00 0.50 1.00 -- 75.13 -93.00 68.00 50 10 \w 54.00 80.00 0.50 1.00 -- 75.13-120.00 -10.00 52 11 \w 38.00 63.00 0.50 1.00 -- 77.04 -93.00 68.00 50 12 \w 63.00 89.00 0.50 1.00 -- 77.04-154.00-167.00 52 13 \w 80.00 105.00 0.50 1.00 -- 77.04 31.00 5.00 50 14 \w -35.00 -10.00 0.50 1.00 -- -57.24 30.00 0.00 50 15 \w 41.00 79.00 0.50 1.00 -- 75.13 -94.00-120.00 76 16 \w 37.00 79.00 0.50 1.00 -- 75.13 -94.00 90.00 84 17 \w 93.00 118.00 0.50 1.00 -- 77.04 30.00 60.00 50 18 \w 92.00 127.00 0.50 1.00 -- 77.04 30.00 90.00 70 19 \w 84.00 110.00 0.50 1.00 -- 81.25-152.00 135.67 52 20 \w 40.00 101.00 0.50 1.00 -- 81.25-108.00 164.97 122 21 \w 43.00 76.00 0.50 1.00 -- 81.25 -73.00 -49.66 66 22 \w 101.00 126.00 0.50 1.00 -- 81.25 8.00 11.67 50 23 \w 43.00 68.00 0.50 1.00 -- 81.25-113.00 85.23 50 24 \w 49.00 75.00 0.50 1.00 -- 81.25 0.00 175.68 52 25 \w 45.00 71.00 0.50 1.00 -- 81.25 0.00 -4.18 52 26 \w 72.00 115.00 0.50 1.00 -- 81.25 -1.00 73.92 86 27 \w 92.00 117.00 0.50 1.00 -- 81.25 58.00 -99.83 50 28 \w 37.00 62.00 0.50 1.00 -- 81.25 -54.00 -86.77 50 29 \w 89.00 114.00 0.50 1.00 -- 81.25 36.00 -48.98 50 30 \w 55.00 106.00 0.50 1.00 -- 81.25-115.00 -98.49 102 31 \w 53.00 105.00 0.50 1.00 -- 81.25 14.00 171.17 104 32 \w 42.00 115.00 0.50 1.00 -- 81.25-138.00 166.72 146 33 \w 47.00 83.00 0.50 1.00 -- 81.25 8.00 11.67 72 34 \w 48.00 74.00 0.50 1.00 -- 81.25 -80.00 162.42 52 35 \w 57.00 92.00 0.50 1.00 -- 81.25-122.00 47.57 70 36 \w 71.00 103.00 0.50 1.00 -- 81.25 163.00-166.54 64 37 \w 56.00 102.00 0.50 1.00 -- 81.25 5.00 116.37 92 38 \w 57.00 83.00 0.50 1.00 -- 75.13-154.00-167.00 52 39 \w -14.00 14.00 0.50 1.00 -- 0.00 102.00 -54.87 56 40 \w -4.00 21.00 0.50 1.00 -- 8.00 97.00 131.50 50 41 \w 5.00 30.00 0.50 1.00 -- 16.00 95.00-117.12 50 42 \w 12.00 38.00 0.50 1.00 -- 20.00 92.00 -97.54 52 43 \w 12.00 37.00 0.50 1.00 -- 20.00 91.00 -13.12 50 44 \w 12.00 37.00 0.50 1.00 -- 20.00 91.00 116.16 50 45 \w 16.00 41.00 0.50 1.00 -- 24.00 91.00 46.18 50 46 \w -41.00 -8.00 0.50 1.00 -- -24.00 104.00 119.35 66 47 \w 16.00 41.00 0.50 1.00 -- 24.00 91.00-178.77 50 48 \w 30.00 55.00 0.50 1.00 -- 28.00 75.00 121.30 50 49 \w 29.00 54.00 0.50 1.00 -- 28.00 77.00 -41.52 50 50 \w 34.00 59.00 0.50 1.00 -- 28.00 67.00 73.59 50 51 \w -60.00 -35.00 0.50 1.00 -- -32.00 -74.00 160.82 50 52 \w 31.00 56.00 0.50 1.00 -- 32.00 80.00 141.99 50 53 \w 35.00 60.00 0.50 1.00 -- 36.00 80.00 157.40 50 54 \w 36.00 61.00 0.50 1.00 -- 36.00 79.00-117.02 50 55 \w 36.00 61.00 0.50 1.00 -- 36.00 78.00 19.56 50 56 \w 37.00 62.00 0.50 1.00 -- 36.00 77.00 79.41 50 57 \w 38.00 63.00 0.50 1.00 -- 36.00 75.00-126.95 50 58 \w 38.00 63.00 0.50 1.00 -- 36.00 76.00 -29.75 50 59 \w 41.00 66.00 0.50 1.00 -- 36.00 69.00 11.30 50 60 \w -67.00 -41.00 0.50 1.00 -- -40.00 -76.00 -26.98 52 61 \w 46.00 71.00 0.50 1.00 -- 40.00 65.00 41.21 50 62 \w 42.00 67.00 0.50 1.00 -- 40.00 75.00 -73.12 50 63 \w 45.00 71.00 0.50 1.00 -- 44.00 79.00 43.11 52 64 \w -69.00 -43.00 0.50 1.00 -- -44.00 -80.00 168.67 52 65 \w 43.00 68.00 0.50 1.00 -- 44.00 80.00 118.00 50 66 \w 46.00 71.00 0.50 1.00 -- 44.00 76.00-105.86 50 67 \w 43.00 68.00 0.50 1.00 -- 44.00 80.00-127.95 50 68 \w -71.00 -46.00 0.50 1.00 -- -44.00 -75.00 -84.86 50 69 \w 43.00 68.00 0.50 1.00 -- 44.00 80.00 98.39 50 70 \w 47.00 72.00 0.50 1.00 -- 48.00 80.00-159.58 50 71 \w 54.00 79.00 0.50 1.00 -- 48.00 65.00 157.95 50 72 \w 47.00 72.00 0.50 1.00 -- 48.00 80.00 -87.35 50 73 \w 57.00 82.00 0.50 1.00 -- 52.00 71.00 15.55 50 74 \w 55.00 80.00 0.50 1.00 -- 52.00 73.00 -40.78 50 75 \w 51.00 76.00 0.50 1.00 -- 52.00 80.00 152.01 50 76 \w 58.00 83.00 0.50 1.00 -- 52.00 66.00 87.42 50 77 \w 56.00 81.00 0.50 1.00 -- 52.00 72.00 -28.48 50 78 \w 57.00 82.00 0.50 1.00 -- 52.00 70.00 -0.66 50 79 \w 59.00 84.00 0.50 1.00 -- 52.00 63.00-160.34 50 80 \w 57.00 82.00 0.50 1.00 -- 52.00 70.00 -55.74 50 81 \w 51.00 76.00 0.50 1.00 -- 52.00 80.00 22.17 50 82 \w 60.00 85.00 0.50 1.00 -- 56.00 72.00 38.63 50 83 \w -87.00 -61.00 0.50 1.00 -- -56.00 -71.00-135.04 52 84 \w 61.00 86.00 0.50 1.00 -- 56.00 71.00-138.13 50 85 \w -34.00 -8.00 0.50 1.00 -- -57.24 30.00 -60.00 52 86 \w -35.00 -8.00 0.50 1.00 -- -57.24 30.00 60.00 54 87 \w -35.00 -10.00 0.50 1.00 -- -57.24 30.00 30.00 50 88 \w -35.00 -10.00 0.50 1.00 -- -57.24 30.00 120.00 50 89 \w -35.00 -10.00 0.50 1.00 -- -57.24 30.00-150.00 50 90 \w -35.00 -9.00 0.50 1.00 -- -57.24 30.00-180.00 52 91 \w -35.00 -10.00 0.50 1.00 -- -57.24 30.00 90.00 50 92 \w 64.00 89.00 0.50 1.00 -- 60.00 72.00 -17.69 50 93 \w 65.00 90.00 0.50 1.00 -- 60.00 70.00 68.82 50 94 \w 67.00 92.00 0.50 1.00 -- 64.00 73.00 1.58 50 95 \w 67.00 92.00 0.50 1.00 -- 64.00 73.00 100.96 50 96 \w -90.00 -64.00 0.50 1.00 -- -64.50 -80.00 -98.53 52 97 \w -99.00 -73.00 0.50 1.00 -- -64.50 -76.00 71.25 52 98 \w -93.00 -67.00 0.50 1.00 -- -64.50 -75.00 27.01 52 99 \w -92.00 -66.00 0.50 1.00 -- -64.50 -79.00 124.34 52 100 \w -94.00 -65.00 0.50 1.00 -- -64.50 -78.00 -60.54 58 101 \w -92.00 -66.00 0.50 1.00 -- -64.50 -78.00-154.59 52 102 \w -92.00 -66.00 0.50 1.00 -- -64.50 -78.00-168.59 52 103 \w -92.00 -66.00 0.50 1.00 -- -64.50 -80.00-174.43 52 104 \w -90.00 -64.00 0.50 1.00 -- -64.50 -79.00 -30.94 52 105 \w -93.00 -67.00 0.50 1.00 -- -64.50 -75.00 49.09 52 106 \w -100.00 -64.00 0.50 1.00 -- -64.50 -80.00 171.02 72 107 \w -91.00 -65.00 0.50 1.00 -- -64.50 -77.00 107.80 52 108 \w -91.00 -65.00 0.50 1.00 -- -64.50 -78.00 148.49 52 109 \w -113.00 -76.00 0.50 1.00 -- -64.50 -36.00 176.94 74 110 \w -90.00 -65.00 0.50 1.00 -- -64.50 -78.00 126.59 50 111 \w -94.00 -68.00 0.50 1.00 -- -64.50 -72.00 -88.97 52 112 \w -91.00 -65.00 0.50 1.00 -- -64.50 -79.00 95.30 52 113 \w -89.00 -64.00 0.50 1.00 -- -64.50 -79.00-123.47 50 114 \w -104.00 -79.00 0.50 1.00 -- -64.50 -71.00 96.47 50 115 \w 68.00 98.00 0.50 1.00 -- 68.00 79.00 9.35 60 116 \w 71.00 96.00 0.50 1.00 -- 68.00 74.00-119.59 50 117 \w 71.00 96.00 0.50 1.00 -- 68.00 74.00 124.66 50 118 \w 36.00 107.00 0.50 1.00 -- 75.13 0.00 120.00 142 119 \w 36.00 62.00 0.50 1.00 -- 75.13 0.00-150.00 52 120 \w 34.00 60.00 0.50 1.00 -- 75.13-125.00 -90.00 52 121 \w 99.00 124.00 0.50 1.00 -- 75.13-154.00-167.00 50 122 \w 82.00 107.00 0.50 1.00 -- 76.00 68.00 -35.09 50 123 \w 44.00 74.00 0.50 1.00 -- 77.04-125.00 -60.00 60 124 \w 79.00 111.00 0.50 1.00 -- 77.04 30.00-180.00 64 125 \w 73.00 105.00 0.50 1.00 -- 77.04-125.00 60.00 64 126 \w 41.00 67.00 0.50 1.00 -- 77.04-125.00 60.00 52 127 \w 38.00 63.00 0.50 1.00 -- 77.04 -94.00 -60.00 50 128 \w 38.00 73.00 0.50 1.00 -- 77.04-125.00-150.00 70 129 \w 48.00 81.00 0.50 1.00 -- 77.04-125.00 30.00 66 130 \w 37.00 81.00 0.50 1.00 -- 77.04-125.00 -30.00 88 131 \w 77.00 102.00 0.50 1.00 -- 77.04-125.00 -60.00 50 132 \w 45.00 90.00 0.50 1.00 -- 77.04 0.00 60.00 90 133 \w 90.00 116.00 0.50 1.00 -- 77.04 30.00 -60.00 52 134 \w 37.00 66.00 0.50 1.00 -- 77.04 -94.00-150.00 58 135 \w 51.00 77.00 0.50 1.00 -- 77.04-125.00 150.00 52 136 \w 79.00 107.00 0.50 1.00 -- 80.00 80.00 -68.87 56 137 \w 83.00 108.00 0.50 1.00 -- 81.25 76.00 -93.25 50 138 \w 91.00 119.00 0.50 1.00 -- 81.25 59.00 7.58 56 139 \w 62.00 120.00 0.50 1.00 -- 81.25 -2.00-161.63 116 140 \w 83.00 110.00 0.50 1.00 -- 81.25-125.00-138.29 54 141 \w 67.00 105.00 0.50 1.00 -- 81.25-118.00-117.96 76 142 \w 35.00 61.00 0.50 1.00 -- 81.25-118.00-117.96 52 143 \w 42.00 68.00 0.50 1.00 -- 81.25-125.00-138.29 52 144 \w 90.00 115.00 0.50 1.00 -- 81.25 54.00 94.00 50 145 \w 65.00 91.00 0.50 1.00 -- 81.25-174.00 37.70 52 146 \w 105.00 130.00 0.50 1.00 -- 81.25 19.00 -31.45 50 147 \w 59.00 85.00 0.50 1.00 -- 81.25 19.00 -31.45 52 148 \w 92.00 118.00 0.50 1.00 -- 81.25 22.00 34.17 52 149 \w 62.00 88.00 0.50 1.00 -- 81.25 22.00 34.17 52 150 \w 83.00 109.00 0.50 1.00 -- 81.25-120.00 84.46 52 151 \w 76.00 111.00 0.50 1.00 -- 81.25-125.00 163.80 70 152 \w 36.00 62.00 0.50 1.00 -- 81.25-120.00 84.46 52 153 \w 51.00 106.00 0.50 1.00 -- 81.25-152.00 -46.25 110 154 \w 42.00 76.00 0.50 1.00 -- 81.25 -67.00-141.95 68 155 \w 95.00 121.00 0.50 1.00 -- 81.25 55.00-125.23 52 156 \w 84.00 109.00 0.50 1.00 -- 81.25 74.00 22.86 50 157 \w 90.00 125.00 0.50 1.00 -- 81.25 47.00-148.61 70 158 \w 87.00 114.00 0.50 1.00 -- 81.25 76.00 32.95 54 159 \w 44.00 73.00 0.50 1.00 -- 81.25 -69.00 12.95 58 160 \w 82.00 116.00 0.50 1.00 -- 81.25 78.00 141.48 68 161 \w 41.00 120.00 0.50 1.00 -- 81.25 -2.00 -76.76 158 162 \w 89.00 115.00 0.50 1.00 -- 81.25 60.00 -14.95 52 163 \w 89.00 130.00 0.50 1.00 -- 81.25-155.00 9.85 82 164 \w 51.00 76.00 0.50 1.00 -- 81.25-155.00 9.85 50 165 \w 58.00 84.00 0.50 1.00 -- 81.25-154.00 134.21 52 166 \w 90.00 116.00 0.50 1.00 -- 81.25-132.00 26.70 52 167 \w 38.00 82.00 0.50 1.00 -- 81.25-132.00 26.70 88 168 \w 84.00 119.00 0.50 1.00 -- 81.25 75.00 95.30 70 169 \w 81.00 118.00 0.50 1.00 -- 81.25 79.00 2.00 74 170 \w 89.00 122.00 0.50 1.00 -- 81.25 58.00-133.33 66 171 \w 61.00 121.00 0.50 1.00 -- 81.25 22.00-145.39 120 172 \w 55.00 80.00 0.50 1.00 -- 60.61-154.00-167.00 50 173 \w 82.00 107.00 0.50 1.00 -- 81.25 77.00 110.58 50 174 \w 51.00 77.00 0.50 1.00 -- 81.25 -73.00-110.12 52 175 \w 37.00 63.00 0.50 1.00 -- 81.25-112.00 30.60 52 176 \w 72.00 98.00 0.50 1.00 -- 81.25-112.00 30.60 52 177 \w 81.00 106.00 0.50 1.00 -- 81.25 79.00 154.27 50 178 \w 80.00 105.00 0.50 1.00 -- 77.04-120.00 -10.00 50 179 \w 51.00 102.00 0.50 1.00 -- 81.25-146.00 82.66 102 180 \w 82.00 107.00 0.50 1.00 -- 81.25 77.00 81.03 50 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix-Arc' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0443184000 _diffrn_orient_matrix_UB_12 0.0608389000 _diffrn_orient_matrix_UB_13 0.0150123000 _diffrn_orient_matrix_UB_21 0.0629204000 _diffrn_orient_matrix_UB_22 0.0381882000 _diffrn_orient_matrix_UB_23 -0.0545154000 _diffrn_orient_matrix_UB_31 -0.0316931000 _diffrn_orient_matrix_UB_32 -0.0090402000 _diffrn_orient_matrix_UB_33 -0.1292336000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _reflns_Friedel_coverage 0.869 _reflns_Friedel_fraction_full 0.991 _reflns_Friedel_fraction_max 0.974 _reflns_number_gt 4241 _reflns_number_total 4355 _reflns_odcompleteness_completeness 99.96 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 74.33 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. Completness statistics refer to single and composite reflections containing twin component 1 only. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'ShelXT n/a (Sheldrick, 2015)' _refine_diff_density_max 0.112 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.032 _refine_ls_abs_structure_details ; Refined as an inversion twin. Flack parameter: the space group\~A? contains symmetry element of the second kind. The NO2 group is disordered and was refined using 2 components with the following restraints: SADI N29A C28 N29B C28 SADI O30A N29A O30B N29B O31A N29A O31B N29B RIGU O30B O31B N29B C28 RIGU O30A O31A N29A C28 ; _refine_ls_abs_structure_Flack -0.1(3) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 311 _refine_ls_number_reflns 4355 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0280 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.9442P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.0720 _refine_special_details ; Refined as a 2-component inversion twin. The NO2 group is disordered and was refined using 2 components with the following restraints: SADI N29A C28 N29B C28 SADI O30A N29A O30B N29B O31A N29A O31B N29B RIGU O30B O31B N29B C28 RIGU O30A O31A N29A C28 The flack parameter was included in the least-square matrix, giving a value of -0.1(3). The more sensitive post refinement Flack parameter determined using 1935 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259) confirm the handleness of a structure with a value of 0.02(7) ; _olex2_refinement_description ; 1. Twinned data refinement Scales: 1.1(3) -0.1(3) 2. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups At 1.5 times of: All C(H,H,H) groups 3. Restrained distances N29A-C28 \\sim N29B-C28 with sigma of 0.02 O30A-N29A \\sim O30B-N29B \\sim O31A-N29A \\sim O31B-N29B with sigma of 0.02 4. Rigid body (RIGU) restrains O30B, O31B, N29B, C28 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 O30A, O31A, N29A, C28 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 5. Others Sof(O30B)=Sof(O31B)=Sof(N29B)=Sof(H28C)=Sof(H28D)=1-FVAR(1) Sof(O30A)=Sof(O31A)=Sof(N29A)=Sof(H28A)=Sof(H28B)=FVAR(1) 6.a Ternary CH refined with riding coordinates: C5(H5) 6.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C28(H28C,H28D), C28(H28A,H28B) 6.c Aromatic/amide H refined with riding coordinates: C9(H9), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C27(H27) 6.d Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C25(H25A,H25B,H25C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary ? 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 O30A O 0.5491(6) 0.6666(9) 0.9008(7) 0.075(3) Uani 0.48(3) 1 d D . P A 1 O30B O 0.5343(5) 0.6350(9) 0.8902(8) 0.070(3) Uani 0.52(3) 1 d D . P A 2 O31A O 0.5022(7) 0.5765(7) 0.8464(16) 0.087(4) Uani 0.48(3) 1 d D . P A 1 O31B O 0.4766(8) 0.5606(4) 0.7948(14) 0.079(3) Uani 0.52(3) 1 d D . P A 2 N1 N 0.64541(8) 0.63118(6) 0.43545(13) 0.0297(3) Uani 1 1 d . . . . . N4 N 0.63487(7) 0.57586(6) 0.66475(13) 0.0295(3) Uani 1 1 d . . . . . N29A N 0.5268(7) 0.6294(8) 0.8246(11) 0.054(3) Uani 0.48(3) 1 d D . P A 1 N29B N 0.5102(6) 0.6103(5) 0.7977(11) 0.0499(19) Uani 0.52(3) 1 d D . P A 2 C2 C 0.65802(10) 0.56355(8) 0.44311(16) 0.0347(4) Uani 1 1 d . . . . . H2A H 0.710417 0.554893 0.450398 0.042 Uiso 1 1 calc R U . . . H2B H 0.639743 0.542484 0.368472 0.042 Uiso 1 1 calc R U . . . C3 C 0.61843(9) 0.53918(7) 0.55506(16) 0.0330(4) Uani 1 1 d . . . . . H3A H 0.565726 0.540571 0.539650 0.040 Uiso 1 1 calc R U . . . H3B H 0.632117 0.494793 0.569188 0.040 Uiso 1 1 calc R U . . . C5 C 0.60915(9) 0.64093(7) 0.65572(15) 0.0300(3) Uani 1 1 d . . . . . H5 H 0.635855 0.666643 0.717568 0.036 Uiso 1 1 calc R U . . . C6 C 0.62321(8) 0.66881(7) 0.53078(14) 0.0275(3) Uani 1 1 d . . . . . C7 C 0.61611(8) 0.73001(7) 0.49134(15) 0.0273(3) Uani 1 1 d . . . . . C8 C 0.63659(8) 0.73050(7) 0.36456(14) 0.0272(3) Uani 1 1 d . . . . . C9 C 0.64449(8) 0.77781(8) 0.27577(15) 0.0295(3) Uani 1 1 d . . . . . H9 H 0.632650 0.820106 0.295099 0.035 Uiso 1 1 calc R U . . . C10 C 0.66959(9) 0.76262(8) 0.15992(15) 0.0321(3) Uani 1 1 d . . . . . C11 C 0.68049(10) 0.81201(10) 0.06268(18) 0.0407(4) Uani 1 1 d . . . . . H11A H 0.678388 0.853818 0.100117 0.061 Uiso 1 1 calc R U . . . H11B H 0.642407 0.808262 0.000770 0.061 Uiso 1 1 calc R U . . . H11C H 0.727774 0.806042 0.023944 0.061 Uiso 1 1 calc R U . . . C12 C 0.68572(10) 0.69934(9) 0.13215(16) 0.0357(4) Uani 1 1 d . . . . . H12 H 0.701678 0.689246 0.051881 0.043 Uiso 1 1 calc R U . . . C13 C 0.67926(9) 0.65181(8) 0.21645(16) 0.0339(4) Uani 1 1 d . . . . . H13 H 0.690849 0.609587 0.196156 0.041 Uiso 1 1 calc R U . . . C14 C 0.65497(9) 0.66809(8) 0.33327(15) 0.0291(3) Uani 1 1 d . . . . . C15 C 0.58880(8) 0.78362(7) 0.56432(15) 0.0273(3) Uani 1 1 d . . . . . C16 C 0.62076(9) 0.80131(7) 0.67446(16) 0.0329(3) Uani 1 1 d . . . . . H16 H 0.662597 0.779864 0.702671 0.040 Uiso 1 1 calc R U . . . C17 C 0.59186(12) 0.85017(8) 0.74348(17) 0.0409(4) Uani 1 1 d . . . . . H17 H 0.613904 0.861632 0.818772 0.049 Uiso 1 1 calc R U . . . C18 C 0.53170(11) 0.88197(8) 0.70362(19) 0.0427(4) Uani 1 1 d . . . . . H18 H 0.511907 0.915084 0.751357 0.051 Uiso 1 1 calc R U . . . C19 C 0.50009(11) 0.86540(8) 0.5932(2) 0.0437(4) Uani 1 1 d . . . . . H19 H 0.458801 0.887605 0.564909 0.052 Uiso 1 1 calc R U . . . C20 C 0.52825(9) 0.81668(8) 0.52384(18) 0.0367(4) Uani 1 1 d . . . . . H20 H 0.506182 0.805744 0.448275 0.044 Uiso 1 1 calc R U . . . C21 C 0.69951(9) 0.56354(7) 0.72880(14) 0.0270(3) Uani 1 1 d . . . . . C22 C 0.71385(9) 0.59352(7) 0.84080(15) 0.0309(3) Uani 1 1 d . . . . . H22 H 0.680776 0.623825 0.871457 0.037 Uiso 1 1 calc R U . . . C23 C 0.77571(9) 0.57941(8) 0.90719(15) 0.0322(3) Uani 1 1 d . . . . . H23 H 0.784600 0.600935 0.981867 0.039 Uiso 1 1 calc R U . . . C24 C 0.82505(9) 0.53452(8) 0.86715(16) 0.0321(3) Uani 1 1 d . . . . . C25 C 0.89062(10) 0.51717(10) 0.9414(2) 0.0448(4) Uani 1 1 d . . . . . H25A H 0.879022 0.481517 0.994640 0.067 Uiso 1 1 calc R U . . . H25B H 0.905309 0.553147 0.991546 0.067 Uiso 1 1 calc R U . . . H25C H 0.930211 0.505560 0.886250 0.067 Uiso 1 1 calc R U . . . C26 C 0.81034(9) 0.50485(8) 0.75678(15) 0.0329(3) Uani 1 1 d . . . . . H26 H 0.842903 0.473801 0.727430 0.039 Uiso 1 1 calc R U . . . C27 C 0.74963(9) 0.51918(7) 0.68821(15) 0.0302(3) Uani 1 1 d . . . . . H27 H 0.741955 0.498469 0.612281 0.036 Uiso 1 1 calc R U . . . C28 C 0.52800(10) 0.64483(9) 0.68538(19) 0.0430(4) Uani 1 1 d D . . . . H28C H 0.513959 0.689436 0.695199 0.052 Uiso 0.52(3) 1 calc R U P A 2 H28D H 0.499954 0.627209 0.616251 0.052 Uiso 0.52(3) 1 calc R U P A 2 H28A H 0.499985 0.613587 0.637850 0.052 Uiso 0.48(3) 1 calc R U P A 1 H28B H 0.508628 0.687367 0.668962 0.052 Uiso 0.48(3) 1 calc R U P A 1 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 O30A 0.076(4) 0.112(7) 0.037(2) 0.001(3) 0.010(2) 0.024(4) O30B 0.064(3) 0.110(8) 0.036(3) 0.014(4) 0.018(2) 0.021(4) O31A 0.078(5) 0.071(5) 0.111(8) 0.050(6) 0.051(5) 0.014(4) O31B 0.079(5) 0.056(3) 0.103(6) 0.022(3) 0.048(4) 0.005(2) N1 0.0375(7) 0.0269(6) 0.0246(6) -0.0021(5) -0.0005(5) 0.0056(5) N4 0.0350(7) 0.0261(6) 0.0273(7) 0.0001(5) 0.0004(5) 0.0043(5) N29A 0.045(4) 0.064(6) 0.053(5) 0.020(4) 0.024(4) 0.021(4) N29B 0.045(4) 0.052(4) 0.053(4) 0.016(3) 0.023(3) 0.016(3) C2 0.0475(9) 0.0269(8) 0.0299(8) -0.0018(6) -0.0015(7) 0.0087(7) C3 0.0381(9) 0.0276(7) 0.0332(9) -0.0010(7) -0.0047(7) 0.0018(6) C5 0.0365(8) 0.0276(7) 0.0258(8) 0.0017(6) 0.0022(6) 0.0072(6) C6 0.0283(7) 0.0296(7) 0.0246(8) -0.0019(6) -0.0006(6) 0.0033(6) C7 0.0284(7) 0.0275(7) 0.0260(8) -0.0012(6) -0.0018(6) 0.0017(6) C8 0.0267(7) 0.0297(7) 0.0253(8) -0.0013(6) -0.0024(6) 0.0012(6) C9 0.0288(7) 0.0302(8) 0.0296(8) 0.0005(6) -0.0029(6) 0.0009(6) C10 0.0289(7) 0.0395(9) 0.0277(8) 0.0041(7) -0.0018(6) 0.0014(6) C11 0.0398(9) 0.0478(10) 0.0345(9) 0.0093(7) 0.0044(7) 0.0033(8) C12 0.0392(9) 0.0434(10) 0.0244(8) -0.0031(7) 0.0002(6) 0.0055(7) C13 0.0404(9) 0.0338(8) 0.0273(8) -0.0043(7) -0.0008(6) 0.0066(7) C14 0.0313(7) 0.0308(8) 0.0253(7) -0.0001(6) -0.0020(6) 0.0025(6) C15 0.0292(8) 0.0259(7) 0.0267(7) 0.0004(6) 0.0026(6) 0.0005(6) C16 0.0412(9) 0.0304(8) 0.0272(8) 0.0012(7) -0.0021(7) 0.0007(7) C17 0.0647(12) 0.0317(8) 0.0263(8) -0.0016(7) 0.0053(8) -0.0044(8) C18 0.0531(11) 0.0302(8) 0.0447(10) -0.0052(8) 0.0184(9) 0.0005(8) C19 0.0344(9) 0.0340(8) 0.0627(12) -0.0034(9) 0.0042(9) 0.0073(8) C20 0.0343(8) 0.0328(8) 0.0431(10) -0.0026(7) -0.0062(7) 0.0043(6) C21 0.0330(8) 0.0233(7) 0.0246(7) 0.0045(6) 0.0029(6) 0.0007(6) C22 0.0395(8) 0.0259(7) 0.0271(8) 0.0009(6) 0.0039(7) 0.0039(6) C23 0.0423(9) 0.0287(7) 0.0256(8) 0.0011(6) 0.0009(7) -0.0022(7) C24 0.0342(8) 0.0327(8) 0.0295(8) 0.0045(6) 0.0024(6) -0.0016(6) C25 0.0382(9) 0.0564(12) 0.0396(10) 0.0007(9) -0.0042(8) 0.0037(8) C26 0.0348(8) 0.0336(8) 0.0304(8) 0.0022(6) 0.0046(7) 0.0057(7) C27 0.0386(8) 0.0273(7) 0.0247(7) -0.0004(6) 0.0014(6) 0.0028(6) C28 0.0413(10) 0.0439(9) 0.0438(11) 0.0126(8) 0.0130(8) 0.0127(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O30A N29A 1.220(10) . ? O30B N29B 1.224(9) . ? O31A N29A 1.239(10) . ? O31B N29B 1.227(8) . ? N1 C2 1.460(2) . ? N1 C6 1.376(2) . ? N1 C14 1.376(2) . ? N4 C3 1.462(2) . ? N4 C5 1.468(2) . ? N4 C21 1.410(2) . ? N29A C28 1.556(10) . ? N29B C28 1.468(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.517(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 H5 1.0000 . ? C5 C6 1.511(2) . ? C5 C28 1.538(2) . ? C6 C7 1.378(2) . ? C7 C8 1.436(2) . ? C7 C15 1.481(2) . ? C8 C9 1.406(2) . ? C8 C14 1.413(2) . ? C9 H9 0.9500 . ? C9 C10 1.386(2) . ? C10 C11 1.508(2) . ? C10 C12 1.412(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12 0.9500 . ? C12 C13 1.373(3) . ? C13 H13 0.9500 . ? C13 C14 1.397(2) . ? C15 C16 1.393(2) . ? C15 C20 1.395(2) . ? C16 H16 0.9500 . ? C16 C17 1.391(2) . ? C17 H17 0.9500 . ? C17 C18 1.373(3) . ? C18 H18 0.9500 . ? C18 C19 1.386(3) . ? C19 H19 0.9500 . ? C19 C20 1.386(3) . ? C20 H20 0.9500 . ? C21 C22 1.405(2) . ? C21 C27 1.396(2) . ? C22 H22 0.9500 . ? C22 C23 1.388(2) . ? C23 H23 0.9500 . ? C23 C24 1.392(2) . ? C24 C25 1.505(2) . ? C24 C26 1.388(2) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26 0.9500 . ? C26 C27 1.384(2) . ? C27 H27 0.9500 . ? C28 H28C 0.9900 . ? C28 H28D 0.9900 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? 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 C2 125.28(14) . . ? C14 N1 C2 126.03(14) . . ? C14 N1 C6 108.67(13) . . ? C3 N4 C5 112.41(13) . . ? C21 N4 C3 118.94(12) . . ? C21 N4 C5 118.93(13) . . ? O30A N29A O31A 125.7(8) . . ? O30A N29A C28 121.7(7) . . ? O31A N29A C28 112.6(8) . . ? O30B N29B O31B 125.3(7) . . ? O30B N29B C28 113.1(6) . . ? O31B N29B C28 121.6(7) . . ? N1 C2 H2A 110.1 . . ? N1 C2 H2B 110.1 . . ? N1 C2 C3 107.81(14) . . ? H2A C2 H2B 108.5 . . ? C3 C2 H2A 110.1 . . ? C3 C2 H2B 110.1 . . ? N4 C3 C2 112.21(13) . . ? N4 C3 H3A 109.2 . . ? N4 C3 H3B 109.2 . . ? C2 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N4 C5 H5 108.1 . . ? N4 C5 C6 112.04(13) . . ? N4 C5 C28 110.68(14) . . ? C6 C5 H5 108.1 . . ? C6 C5 C28 109.71(13) . . ? C28 C5 H5 108.1 . . ? N1 C6 C5 120.44(13) . . ? N1 C6 C7 109.97(14) . . ? C7 C6 C5 129.58(14) . . ? C6 C7 C8 106.46(13) . . ? C6 C7 C15 126.31(14) . . ? C8 C7 C15 127.14(14) . . ? C9 C8 C7 134.29(15) . . ? C9 C8 C14 118.77(14) . . ? C14 C8 C7 106.86(13) . . ? C8 C9 H9 120.1 . . ? C10 C9 C8 119.85(15) . . ? C10 C9 H9 120.1 . . ? C9 C10 C11 121.70(16) . . ? C9 C10 C12 119.29(15) . . ? C12 C10 C11 119.01(16) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12 118.7 . . ? C13 C12 C10 122.68(16) . . ? C13 C12 H12 118.7 . . ? C12 C13 H13 121.4 . . ? C12 C13 C14 117.27(15) . . ? C14 C13 H13 121.4 . . ? N1 C14 C8 108.01(13) . . ? N1 C14 C13 129.86(15) . . ? C13 C14 C8 122.12(15) . . ? C16 C15 C7 121.91(14) . . ? C16 C15 C20 118.60(15) . . ? C20 C15 C7 119.47(15) . . ? C15 C16 H16 119.8 . . ? C17 C16 C15 120.47(16) . . ? C17 C16 H16 119.8 . . ? C16 C17 H17 119.7 . . ? C18 C17 C16 120.52(18) . . ? C18 C17 H17 119.7 . . ? C17 C18 H18 120.2 . . ? C17 C18 C19 119.51(17) . . ? C19 C18 H18 120.2 . . ? C18 C19 H19 119.7 . . ? C18 C19 C20 120.51(18) . . ? C20 C19 H19 119.7 . . ? C15 C20 H20 119.8 . . ? C19 C20 C15 120.39(17) . . ? C19 C20 H20 119.8 . . ? C22 C21 N4 120.51(14) . . ? C27 C21 N4 122.11(14) . . ? C27 C21 C22 117.28(15) . . ? C21 C22 H22 119.6 . . ? C23 C22 C21 120.83(14) . . ? C23 C22 H22 119.6 . . ? C22 C23 H23 119.2 . . ? C22 C23 C24 121.68(16) . . ? C24 C23 H23 119.2 . . ? C23 C24 C25 121.85(16) . . ? C26 C24 C23 117.17(16) . . ? C26 C24 C25 120.96(16) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26 119.0 . . ? C27 C26 C24 121.95(16) . . ? C27 C26 H26 119.0 . . ? C21 C27 H27 119.5 . . ? C26 C27 C21 121.08(15) . . ? C26 C27 H27 119.5 . . ? N29A C28 H28A 111.4 . . ? N29A C28 H28B 111.4 . . ? N29B C28 C5 111.6(5) . . ? N29B C28 H28C 109.3 . . ? N29B C28 H28D 109.3 . . ? C5 C28 N29A 102.0(5) . . ? C5 C28 H28C 109.3 . . ? C5 C28 H28D 109.3 . . ? C5 C28 H28A 111.4 . . ? C5 C28 H28B 111.4 . . ? H28C C28 H28D 108.0 . . ? H28A C28 H28B 109.2 . . ? 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 O30A N29A C28 C5 71.8(9) . . . . ? O30B N29B C28 C5 69.2(8) . . . . ? O31A N29A C28 C5 -107.4(7) . . . . ? O31B N29B C28 C5 -108.3(8) . . . . ? N1 C2 C3 N4 -50.43(18) . . . . ? N1 C6 C7 C8 -1.23(18) . . . . ? N1 C6 C7 C15 175.70(14) . . . . ? N4 C5 C6 N1 10.8(2) . . . . ? N4 C5 C6 C7 -170.45(16) . . . . ? N4 C5 C28 N29A 68.7(7) . . . . ? N4 C5 C28 N29B 47.7(7) . . . . ? N4 C21 C22 C23 176.91(15) . . . . ? N4 C21 C27 C26 -175.63(15) . . . . ? C2 N1 C6 C5 -0.5(2) . . . . ? C2 N1 C6 C7 -179.50(15) . . . . ? C2 N1 C14 C8 179.77(15) . . . . ? C2 N1 C14 C13 -1.3(3) . . . . ? C3 N4 C5 C6 -41.86(18) . . . . ? C3 N4 C5 C28 80.94(17) . . . . ? C3 N4 C21 C22 -173.88(14) . . . . ? C3 N4 C21 C27 2.5(2) . . . . ? C5 N4 C3 C2 64.82(17) . . . . ? C5 N4 C21 C22 42.7(2) . . . . ? C5 N4 C21 C27 -140.89(15) . . . . ? C5 C6 C7 C8 179.93(15) . . . . ? C5 C6 C7 C15 -3.1(3) . . . . ? C6 N1 C2 C3 19.6(2) . . . . ? C6 N1 C14 C8 -1.41(17) . . . . ? C6 N1 C14 C13 177.56(17) . . . . ? C6 C5 C28 N29A -167.2(7) . . . . ? C6 C5 C28 N29B 171.8(6) . . . . ? C6 C7 C8 C9 -176.09(17) . . . . ? C6 C7 C8 C14 0.34(17) . . . . ? C6 C7 C15 C16 57.4(2) . . . . ? C6 C7 C15 C20 -120.96(19) . . . . ? C7 C8 C9 C10 176.41(17) . . . . ? C7 C8 C14 N1 0.65(17) . . . . ? C7 C8 C14 C13 -178.42(15) . . . . ? C7 C15 C16 C17 -177.18(16) . . . . ? C7 C15 C20 C19 177.42(16) . . . . ? C8 C7 C15 C16 -126.26(18) . . . . ? C8 C7 C15 C20 55.3(2) . . . . ? C8 C9 C10 C11 -178.61(15) . . . . ? C8 C9 C10 C12 1.1(2) . . . . ? C9 C8 C14 N1 177.74(14) . . . . ? C9 C8 C14 C13 -1.3(2) . . . . ? C9 C10 C12 C13 -1.6(3) . . . . ? C10 C12 C13 C14 0.6(3) . . . . ? C11 C10 C12 C13 178.10(17) . . . . ? C12 C13 C14 N1 -177.99(16) . . . . ? C12 C13 C14 C8 0.9(2) . . . . ? C14 N1 C2 C3 -161.74(15) . . . . ? C14 N1 C6 C5 -179.37(14) . . . . ? C14 N1 C6 C7 1.67(18) . . . . ? C14 C8 C9 C10 0.3(2) . . . . ? C15 C7 C8 C9 7.0(3) . . . . ? C15 C7 C8 C14 -176.55(15) . . . . ? C15 C16 C17 C18 -0.5(3) . . . . ? C16 C15 C20 C19 -1.0(3) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? C17 C18 C19 C20 0.7(3) . . . . ? C18 C19 C20 C15 0.1(3) . . . . ? C20 C15 C16 C17 1.2(2) . . . . ? C21 N4 C3 C2 -80.85(17) . . . . ? C21 N4 C5 C6 103.81(16) . . . . ? C21 N4 C5 C28 -133.39(16) . . . . ? C21 C22 C23 C24 -1.2(2) . . . . ? C22 C21 C27 C26 0.9(2) . . . . ? C22 C23 C24 C25 -177.45(16) . . . . ? C22 C23 C24 C26 0.8(2) . . . . ? C23 C24 C26 C27 0.4(2) . . . . ? C24 C26 C27 C21 -1.3(3) . . . . ? C25 C24 C26 C27 178.71(16) . . . . ? C27 C21 C22 C23 0.3(2) . . . . ? C28 C5 C6 N1 -112.54(17) . . . . ? C28 C5 C6 C7 66.2(2) . . . . ? _shelx_res_file ; TITL ajgi-879-3-1_a.res in Iba2 ajgi879b.res created by SHELXL-2018/3 at 16:14:08 on 05-Dec-2019 REM Old TITL AJGI-879-3-1 in Iba2 REM SHELXT solution in Iba2 REM R1 0.124, Rweak 0.079, Alpha 0.004, Orientation as input REM Flack x = -9.990 ( 2.250 ) from Parsons' quotients REM Formula found by SHELXT: C28 N4 O CELL 1.54184 18.502163 21.279519 10.925189 90 90 90 ZERR 8 0.00012 0.00014 0.000067 0 0 0 LATT -2 SYMM -X,-Y,+Z SYMM 0.5+X,0.5-Y,+Z SYMM 0.5-X,0.5+Y,+Z SFAC C H N O UNIT 208 200 24 16 SADI N29A C28 N29B C28 SADI O30A N29A O30B N29B O31A N29A O31B N29B RIGU O30B O31B N29B C28 RIGU O30A O31A N29A C28 L.S. 4 PLAN 1 TEMP -123 CONF BOND $H LIST 6 MORE -1 fmap 2 acta TWIN -1 0 0 0 -1 0 0 0 -1 2 REM REM REM WGHT 0.044300 0.944200 BASF -0.08158 FVAR 3.55366 0.48460 PART 1 O30A 4 0.549089 0.666645 0.900778 21.00000 0.07579 0.11215 = 0.03741 0.00098 0.01024 0.02440 PART 0 PART 2 O30B 4 0.534337 0.635034 0.890217 -21.00000 0.06372 0.11007 = 0.03577 0.01397 0.01786 0.02084 PART 0 PART 1 O31A 4 0.502249 0.576473 0.846441 21.00000 0.07800 0.07063 = 0.11099 0.04973 0.05104 0.01369 PART 0 PART 2 O31B 4 0.476650 0.560554 0.794799 -21.00000 0.07933 0.05555 = 0.10263 0.02160 0.04759 0.00525 PART 0 N1 3 0.645405 0.631182 0.435452 11.00000 0.03754 0.02690 = 0.02458 -0.00205 -0.00049 0.00558 N4 3 0.634866 0.575857 0.664747 11.00000 0.03505 0.02609 = 0.02732 0.00014 0.00043 0.00435 PART 1 N29A 3 0.526835 0.629448 0.824646 21.00000 0.04451 0.06401 = 0.05269 0.02037 0.02394 0.02130 PART 0 PART 2 N29B 3 0.510165 0.610280 0.797747 -21.00000 0.04484 0.05163 = 0.05325 0.01626 0.02304 0.01587 PART 0 C2 1 0.658020 0.563546 0.443106 11.00000 0.04753 0.02686 = 0.02985 -0.00183 -0.00151 0.00874 AFIX 23 H2A 2 0.710417 0.554893 0.450398 11.00000 -1.20000 H2B 2 0.639743 0.542484 0.368472 11.00000 -1.20000 AFIX 0 C3 1 0.618430 0.539180 0.555059 11.00000 0.03808 0.02763 = 0.03320 -0.00098 -0.00473 0.00184 AFIX 23 H3A 2 0.565726 0.540571 0.539650 11.00000 -1.20000 H3B 2 0.632117 0.494793 0.569188 11.00000 -1.20000 AFIX 0 C5 1 0.609147 0.640935 0.655723 11.00000 0.03649 0.02764 = 0.02578 0.00173 0.00216 0.00724 AFIX 13 H5 2 0.635855 0.666643 0.717568 11.00000 -1.20000 AFIX 0 C6 1 0.623206 0.668809 0.530780 11.00000 0.02833 0.02957 = 0.02457 -0.00186 -0.00058 0.00331 C7 1 0.616113 0.730013 0.491337 11.00000 0.02837 0.02750 = 0.02605 -0.00124 -0.00185 0.00171 C8 1 0.636590 0.730504 0.364559 11.00000 0.02672 0.02972 = 0.02529 -0.00132 -0.00236 0.00118 C9 1 0.644488 0.777814 0.275769 11.00000 0.02876 0.03015 = 0.02961 0.00045 -0.00286 0.00087 AFIX 43 H9 2 0.632650 0.820106 0.295099 11.00000 -1.20000 AFIX 0 C10 1 0.669591 0.762619 0.159923 11.00000 0.02892 0.03950 = 0.02774 0.00405 -0.00183 0.00137 C11 1 0.680494 0.812008 0.062676 11.00000 0.03979 0.04779 = 0.03452 0.00929 0.00445 0.00329 AFIX 137 H11A 2 0.678388 0.853818 0.100117 11.00000 -1.50000 H11B 2 0.642407 0.808262 0.000770 11.00000 -1.50000 H11C 2 0.727774 0.806042 0.023944 11.00000 -1.50000 AFIX 0 C12 1 0.685716 0.699342 0.132154 11.00000 0.03924 0.04335 = 0.02436 -0.00309 0.00024 0.00550 AFIX 43 H12 2 0.701678 0.689246 0.051881 11.00000 -1.20000 AFIX 0 C13 1 0.679265 0.651812 0.216454 11.00000 0.04040 0.03384 = 0.02735 -0.00432 -0.00080 0.00656 AFIX 43 H13 2 0.690849 0.609587 0.196156 11.00000 -1.20000 AFIX 0 C14 1 0.654972 0.668092 0.333270 11.00000 0.03126 0.03079 = 0.02533 -0.00013 -0.00198 0.00246 C15 1 0.588795 0.783624 0.564320 11.00000 0.02916 0.02591 = 0.02671 0.00043 0.00263 0.00045 C16 1 0.620759 0.801314 0.674464 11.00000 0.04124 0.03037 = 0.02723 0.00124 -0.00214 0.00070 AFIX 43 H16 2 0.662597 0.779864 0.702671 11.00000 -1.20000 AFIX 0 C17 1 0.591857 0.850174 0.743479 11.00000 0.06466 0.03175 = 0.02629 -0.00159 0.00532 -0.00439 AFIX 43 H17 2 0.613904 0.861632 0.818772 11.00000 -1.20000 AFIX 0 C18 1 0.531701 0.881975 0.703619 11.00000 0.05313 0.03023 = 0.04475 -0.00522 0.01838 0.00049 AFIX 43 H18 2 0.511907 0.915084 0.751357 11.00000 -1.20000 AFIX 0 C19 1 0.500088 0.865401 0.593229 11.00000 0.03444 0.03402 = 0.06269 -0.00344 0.00421 0.00732 AFIX 43 H19 2 0.458801 0.887605 0.564909 11.00000 -1.20000 AFIX 0 C20 1 0.528248 0.816684 0.523844 11.00000 0.03426 0.03276 = 0.04307 -0.00263 -0.00615 0.00428 AFIX 43 H20 2 0.506182 0.805744 0.448275 11.00000 -1.20000 AFIX 0 C21 1 0.699515 0.563537 0.728801 11.00000 0.03304 0.02333 = 0.02457 0.00449 0.00295 0.00068 C22 1 0.713845 0.593517 0.840798 11.00000 0.03955 0.02591 = 0.02713 0.00092 0.00392 0.00394 AFIX 43 H22 2 0.680776 0.623825 0.871457 11.00000 -1.20000 AFIX 0 C23 1 0.775708 0.579406 0.907193 11.00000 0.04231 0.02871 = 0.02555 0.00106 0.00087 -0.00221 AFIX 43 H23 2 0.784600 0.600935 0.981867 11.00000 -1.20000 AFIX 0 C24 1 0.825046 0.534519 0.867155 11.00000 0.03423 0.03269 = 0.02951 0.00451 0.00237 -0.00159 C25 1 0.890617 0.517173 0.941371 11.00000 0.03825 0.05644 = 0.03962 0.00072 -0.00420 0.00370 AFIX 137 H25A 2 0.879022 0.481517 0.994640 11.00000 -1.50000 H25B 2 0.905309 0.553147 0.991546 11.00000 -1.50000 H25C 2 0.930211 0.505560 0.886250 11.00000 -1.50000 AFIX 0 C26 1 0.810337 0.504854 0.756778 11.00000 0.03477 0.03356 = 0.03036 0.00220 0.00462 0.00569 AFIX 43 H26 2 0.842903 0.473801 0.727430 11.00000 -1.20000 AFIX 0 C27 1 0.749632 0.519175 0.688213 11.00000 0.03855 0.02728 = 0.02467 -0.00039 0.00140 0.00278 AFIX 43 H27 2 0.741955 0.498469 0.612281 11.00000 -1.20000 AFIX 0 C28 1 0.527995 0.644825 0.685379 11.00000 0.04130 0.04390 = 0.04379 0.01263 0.01304 0.01274 PART 2 AFIX 23 H28C 2 0.513959 0.689436 0.695199 -21.00000 -1.20000 H28D 2 0.499954 0.627209 0.616251 -21.00000 -1.20000 AFIX 23 PART 0 PART 1 H28A 2 0.499985 0.613587 0.637850 21.00000 -1.20000 H28B 2 0.508628 0.687367 0.668962 21.00000 -1.20000 AFIX 0 HKLF 4 REM ajgi-879-3-1_a.res in Iba2 REM wR2 = 0.0720, GooF = S = 1.048, Restrained GooF = 1.047 for all data REM R1 = 0.0280 for 4241 Fo > 4sig(Fo) and 0.0289 for all 4355 data REM 311 parameters refined using 44 restraints END WGHT 0.0443 0.9442 REM Highest difference peak 0.112, deepest hole -0.181, 1-sigma level 0.032 Q1 1 0.8860 0.5233 1.0282 11.00000 0.05 0.11 ; _shelx_res_checksum 29168 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.060 _oxdiff_exptl_absorpt_empirical_full_min 0.654 loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 1.1(3) 2 -0.1(3) ####################################################################### # # 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_ajgi831_2_1 _database_code_depnum_ccdc_archive 'CCDC 2015203' loop_ _audit_author_name _audit_author_address 'Celine Besnard' ;university of Geneva Switzerland ; _audit_update_record ; 2020-07-09 deposited with the CCDC. 2020-11-23 downloaded from the CCDC. ; _audit_creation_date 2018-07-06 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number 2017/1 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C25 H24 N2' _chemical_formula_sum 'C25 H24 N2' _chemical_formula_weight 352.46 _chemical_melting_point ? _chemical_oxdiff_formula 'C25 H24 N2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' 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' '-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 21.3021(10) _cell_length_b 7.7181(4) _cell_length_c 23.5444(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3871.0(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2532 _cell_measurement_temperature 180.01(10) _cell_measurement_theta_max 70.6850 _cell_measurement_theta_min 4.2830 _shelx_estimated_absorpt_T_max 0.989 _shelx_estimated_absorpt_T_min 0.787 _exptl_absorpt_coefficient_mu 0.539 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.806 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description plate _exptl_crystal_F_000 1504 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 1 0.0181 1 0 -1 0.0181 1 1 -1 0.2016 -1 -1 1 0.2016 0 0 -1 0.0100 0 0 1 0.0100 _exptl_crystal_size_max 0.466 _exptl_crystal_size_mid 0.067 _exptl_crystal_size_min 0.02 loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.9992 0.0008 1.0032 -0.0224 -0.0916 -0.0252 0.9992 -0.0008 -1.0032 0.0224 0.0916 0.0252 0.9964 0.9989 -1.0054 -0.0012 0.0439 0.2175 -0.9964 -0.9989 1.0054 0.0012 -0.0439 -0.2175 -0.0002 -0.0006 -1.0014 -0.0368 0.0535 0.0087 0.0002 0.0006 1.0014 0.0368 -0.0535 -0.0087 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_unetI/netI 0.0524 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 8929 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.460 _diffrn_reflns_theta_min 3.755 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 180.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.4670 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -66.00 -27.00 1.00 20.00 -- -41.74 38.00 -60.00 39 2 \w -64.00 33.00 1.00 20.00 -- -41.74 38.00 30.00 97 3 \w 121.00 170.00 1.00 30.00 -- 100.00 45.00-120.00 49 4 \w 95.00 126.00 1.00 30.00 -- 100.00 125.00-180.00 31 5 \w 83.00 109.00 1.00 30.00 -- 100.00-125.00-120.00 26 6 \w 94.00 172.00 1.00 30.00 -- 100.00 125.00-120.00 78 7 \w 38.00 113.00 1.00 30.00 -- 100.00-125.00 90.00 75 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0592905000 _diffrn_orient_matrix_UB_12 -0.0233060000 _diffrn_orient_matrix_UB_13 0.0367478000 _diffrn_orient_matrix_UB_21 0.0379969000 _diffrn_orient_matrix_UB_22 -0.0476914000 _diffrn_orient_matrix_UB_23 -0.0534013000 _diffrn_orient_matrix_UB_31 0.0165575000 _diffrn_orient_matrix_UB_32 0.1923861000 _diffrn_orient_matrix_UB_33 -0.0088319000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2423 _reflns_number_total 3621 _reflns_odcompleteness_completeness 99.80 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _refine_diff_density_max 0.192 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef 0.00040(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)' _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 247 _refine_ls_number_reflns 3621 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0549 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0708P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1293 _refine_ls_wR_factor_ref 0.1547 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C20(H20A,H20B) 2.b Aromatic/amide H refined with riding coordinates: C6(H6), C7(H7), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C22(H22), C23(H23), C25(H25), C26(H26) 2.c Idealised Me refined as rotating group: C9(H9A,H9B,H9C), C27(H27A,H27B,H27C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary ? 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 0.20143(8) 0.2752(2) 0.30286(7) 0.0329(4) Uani 1 1 d . . . . . N4 N 0.25698(8) 0.2800(2) 0.19689(7) 0.0349(4) Uani 1 1 d . . . . . C2 C 0.16512(10) 0.3420(3) 0.25497(9) 0.0368(5) Uani 1 1 d . . . . . H2A H 0.168784 0.469774 0.253596 0.044 Uiso 1 1 calc R . . . . H2B H 0.120268 0.312257 0.260105 0.044 Uiso 1 1 calc R . . . . C3 C 0.18874(9) 0.2653(3) 0.19976(9) 0.0373(5) Uani 1 1 d . . . . . H3A H 0.176379 0.141884 0.197348 0.045 Uiso 1 1 calc R . . . . H3B H 0.169608 0.327408 0.167296 0.045 Uiso 1 1 calc R . . . . C5 C 0.29401(10) 0.2437(3) 0.15032(9) 0.0366(5) Uani 1 1 d . . . . . C6 C 0.27637(11) 0.2042(3) 0.09489(10) 0.0457(6) Uani 1 1 d . . . . . H6 H 0.233419 0.197838 0.084234 0.055 Uiso 1 1 calc R . . . . C7 C 0.32362(12) 0.1745(3) 0.05602(10) 0.0494(6) Uani 1 1 d . . . . . H7 H 0.312709 0.146836 0.017959 0.059 Uiso 1 1 calc R . . . . C8 C 0.38736(11) 0.1839(3) 0.07097(10) 0.0455(6) Uani 1 1 d . . . . . C9 C 0.43695(12) 0.1540(4) 0.02606(11) 0.0595(7) Uani 1 1 d . . . . . H9A H 0.478097 0.187968 0.040991 0.089 Uiso 1 1 calc GR . . . . H9B H 0.427178 0.223647 -0.007598 0.089 Uiso 1 1 calc GR . . . . H9C H 0.437724 0.031046 0.015700 0.089 Uiso 1 1 calc GR . . . . C10 C 0.40401(11) 0.2229(3) 0.12643(10) 0.0402(5) Uani 1 1 d . . . . . H10 H 0.447059 0.229883 0.136703 0.048 Uiso 1 1 calc R . . . . C11 C 0.35731(9) 0.2522(3) 0.16749(9) 0.0346(5) Uani 1 1 d . . . . . C12 C 0.35734(9) 0.2915(3) 0.22729(9) 0.0323(5) Uani 1 1 d . . . . . C13 C 0.41090(9) 0.3001(3) 0.26665(9) 0.0333(5) Uani 1 1 d . . . . . C14 C 0.46207(9) 0.1873(3) 0.26154(10) 0.0389(5) Uani 1 1 d . . . . . H14 H 0.463822 0.108605 0.230542 0.047 Uiso 1 1 calc R . . . . C15 C 0.50998(10) 0.1890(3) 0.30099(10) 0.0469(6) Uani 1 1 d . . . . . H15 H 0.544265 0.111221 0.296992 0.056 Uiso 1 1 calc R . . . . C16 C 0.50851(11) 0.3030(4) 0.34629(11) 0.0522(6) Uani 1 1 d . . . . . H16 H 0.541496 0.303027 0.373446 0.063 Uiso 1 1 calc R . . . . C17 C 0.45883(10) 0.4167(3) 0.35186(10) 0.0473(6) Uani 1 1 d . . . . . H17 H 0.457650 0.495172 0.382930 0.057 Uiso 1 1 calc R . . . . C18 C 0.41073(10) 0.4168(3) 0.31228(9) 0.0400(5) Uani 1 1 d . . . . . H18 H 0.377159 0.496935 0.316112 0.048 Uiso 1 1 calc R . . . . C19 C 0.29508(10) 0.3057(3) 0.24299(9) 0.0324(5) Uani 1 1 d . . . . . C20 C 0.26668(9) 0.3382(3) 0.29981(9) 0.0342(5) Uani 1 1 d . . . . . H20A H 0.292089 0.279442 0.329273 0.041 Uiso 1 1 calc R . . . . H20B H 0.267432 0.464152 0.307802 0.041 Uiso 1 1 calc R . . . . C21 C 0.17497(10) 0.3010(3) 0.35807(9) 0.0352(5) Uani 1 1 d . . . . . C22 C 0.20338(11) 0.2200(3) 0.40421(10) 0.0412(5) Uani 1 1 d . . . . . H22 H 0.239817 0.151184 0.398489 0.049 Uiso 1 1 calc R . . . . C23 C 0.17906(11) 0.2387(3) 0.45813(10) 0.0455(6) Uani 1 1 d . . . . . H23 H 0.199287 0.182421 0.489002 0.055 Uiso 1 1 calc R . . . . C24 C 0.12566(11) 0.3378(3) 0.46858(10) 0.0475(6) Uani 1 1 d . . . . . C25 C 0.09771(11) 0.4157(4) 0.42237(11) 0.0535(7) Uani 1 1 d . . . . . H25 H 0.060763 0.482381 0.428070 0.064 Uiso 1 1 calc R . . . . C26 C 0.12167(10) 0.4001(3) 0.36785(10) 0.0459(6) Uani 1 1 d . . . . . H26 H 0.101551 0.457366 0.337119 0.055 Uiso 1 1 calc R . . . . C27 C 0.10070(13) 0.3576(4) 0.52809(11) 0.0632(8) Uani 1 1 d . . . . . H27A H 0.107198 0.249410 0.549096 0.095 Uiso 1 1 calc GR . . . . H27B H 0.055735 0.384016 0.526625 0.095 Uiso 1 1 calc GR . . . . H27C H 0.122930 0.452084 0.547265 0.095 Uiso 1 1 calc GR . . . . 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 0.0271(8) 0.0380(9) 0.0337(9) 0.0011(8) -0.0009(7) 0.0001(8) N4 0.0302(9) 0.0433(10) 0.0313(9) -0.0005(8) -0.0024(7) 0.0010(8) C2 0.0307(11) 0.0399(11) 0.0398(12) 0.0011(10) -0.0016(9) 0.0010(9) C3 0.0289(10) 0.0452(12) 0.0378(12) 0.0026(10) -0.0043(9) -0.0002(10) C5 0.0371(11) 0.0405(11) 0.0322(11) 0.0006(10) 0.0003(9) 0.0024(10) C6 0.0412(12) 0.0602(15) 0.0356(12) -0.0021(12) -0.0044(10) 0.0003(11) C7 0.0537(14) 0.0622(15) 0.0322(12) -0.0050(12) -0.0004(11) 0.0010(13) C8 0.0501(13) 0.0505(13) 0.0360(12) 0.0029(11) 0.0054(11) 0.0045(12) C9 0.0587(16) 0.0773(18) 0.0424(14) -0.0006(14) 0.0123(12) 0.0100(15) C10 0.0391(11) 0.0438(12) 0.0376(12) 0.0036(11) 0.0024(10) 0.0026(10) C11 0.0346(11) 0.0352(10) 0.0341(11) 0.0040(9) -0.0002(9) 0.0020(9) C12 0.0298(10) 0.0342(10) 0.0330(10) 0.0024(9) 0.0012(9) -0.0010(9) C13 0.0288(10) 0.0374(11) 0.0338(11) 0.0025(10) 0.0022(9) -0.0033(9) C14 0.0311(11) 0.0438(12) 0.0418(12) 0.0042(10) 0.0049(9) -0.0009(10) C15 0.0318(11) 0.0595(14) 0.0494(14) 0.0094(13) -0.0003(11) 0.0010(11) C16 0.0357(12) 0.0766(17) 0.0442(13) 0.0101(14) -0.0089(11) -0.0079(13) C17 0.0418(13) 0.0625(15) 0.0377(12) -0.0038(12) -0.0008(10) -0.0108(12) C18 0.0358(11) 0.0447(11) 0.0396(12) -0.0022(10) 0.0029(10) -0.0047(10) C19 0.0321(11) 0.0313(10) 0.0339(11) 0.0003(9) -0.0030(9) -0.0021(9) C20 0.0279(10) 0.0394(11) 0.0353(11) -0.0030(10) 0.0008(9) -0.0034(9) C21 0.0330(10) 0.0346(10) 0.0381(12) -0.0036(10) 0.0019(9) -0.0053(9) C22 0.0394(11) 0.0475(12) 0.0367(12) -0.0021(11) -0.0007(10) 0.0014(11) C23 0.0476(13) 0.0529(13) 0.0359(12) -0.0012(11) -0.0011(10) -0.0017(12) C24 0.0469(13) 0.0558(14) 0.0398(13) -0.0051(12) 0.0096(11) -0.0053(12) C25 0.0446(13) 0.0651(15) 0.0509(15) -0.0036(14) 0.0106(12) 0.0100(12) C26 0.0413(12) 0.0539(14) 0.0426(13) 0.0016(12) 0.0049(11) 0.0087(12) C27 0.0629(17) 0.0818(19) 0.0449(15) -0.0072(15) 0.0129(13) -0.0009(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 1.461(3) . ? N1 C20 1.474(2) . ? N1 C21 1.431(3) . ? N4 C3 1.460(3) . ? N4 C5 1.379(3) . ? N4 C19 1.370(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.514(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C6 1.392(3) . ? C5 C11 1.409(3) . ? C6 H6 0.9500 . ? C6 C7 1.380(3) . ? C7 H7 0.9500 . ? C7 C8 1.404(3) . ? C8 C9 1.512(3) . ? C8 C10 1.386(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10 0.9500 . ? C10 C11 1.405(3) . ? C11 C12 1.440(3) . ? C12 C13 1.472(3) . ? C12 C19 1.381(3) . ? C13 C14 1.400(3) . ? C13 C18 1.402(3) . ? C14 H14 0.9500 . ? C14 C15 1.380(3) . ? C15 H15 0.9500 . ? C15 C16 1.383(4) . ? C16 H16 0.9500 . ? C16 C17 1.381(4) . ? C17 H17 0.9500 . ? C17 C18 1.385(3) . ? C18 H18 0.9500 . ? C19 C20 1.490(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.392(3) . ? C21 C26 1.388(3) . ? C22 H22 0.9500 . ? C22 C23 1.379(3) . ? C23 H23 0.9500 . ? C23 C24 1.393(3) . ? C24 C25 1.378(4) . ? C24 C27 1.506(3) . ? C25 H25 0.9500 . ? C25 C26 1.386(3) . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 C20 110.18(16) . . ? C21 N1 C2 116.31(16) . . ? C21 N1 C20 111.70(16) . . ? C5 N4 C3 126.20(17) . . ? C19 N4 C3 124.38(17) . . ? C19 N4 C5 108.69(17) . . ? N1 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? N1 C2 C3 110.40(16) . . ? H2A C2 H2B 108.1 . . ? C3 C2 H2A 109.6 . . ? C3 C2 H2B 109.6 . . ? N4 C3 C2 109.90(17) . . ? N4 C3 H3A 109.7 . . ? N4 C3 H3B 109.7 . . ? C2 C3 H3A 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? N4 C5 C6 129.5(2) . . ? N4 C5 C11 108.04(18) . . ? C6 C5 C11 122.5(2) . . ? C5 C6 H6 121.3 . . ? C7 C6 C5 117.5(2) . . ? C7 C6 H6 121.3 . . ? C6 C7 H7 119.0 . . ? C6 C7 C8 122.0(2) . . ? C8 C7 H7 119.0 . . ? C7 C8 C9 119.5(2) . . ? C10 C8 C7 119.6(2) . . ? C10 C8 C9 120.9(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10 119.9 . . ? C8 C10 C11 120.1(2) . . ? C11 C10 H10 119.9 . . ? C5 C11 C12 106.90(18) . . ? C10 C11 C5 118.2(2) . . ? C10 C11 C12 134.9(2) . . ? C11 C12 C13 128.71(19) . . ? C19 C12 C11 106.14(18) . . ? C19 C12 C13 124.93(19) . . ? C14 C13 C12 121.43(19) . . ? C14 C13 C18 117.9(2) . . ? C18 C13 C12 120.63(19) . . ? C13 C14 H14 119.6 . . ? C15 C14 C13 120.8(2) . . ? C15 C14 H14 119.6 . . ? C14 C15 H15 119.7 . . ? C14 C15 C16 120.6(2) . . ? C16 C15 H15 119.7 . . ? C15 C16 H16 120.2 . . ? C17 C16 C15 119.7(2) . . ? C17 C16 H16 120.2 . . ? C16 C17 H17 119.9 . . ? C16 C17 C18 120.2(2) . . ? C18 C17 H17 119.9 . . ? C13 C18 H18 119.5 . . ? C17 C18 C13 120.9(2) . . ? C17 C18 H18 119.5 . . ? N4 C19 C12 110.21(18) . . ? N4 C19 C20 119.70(18) . . ? C12 C19 C20 130.07(18) . . ? N1 C20 C19 111.77(17) . . ? N1 C20 H20A 109.3 . . ? N1 C20 H20B 109.3 . . ? C19 C20 H20A 109.3 . . ? C19 C20 H20B 109.3 . . ? H20A C20 H20B 107.9 . . ? C22 C21 N1 118.35(18) . . ? C26 C21 N1 123.4(2) . . ? C26 C21 C22 118.3(2) . . ? C21 C22 H22 119.7 . . ? C23 C22 C21 120.5(2) . . ? C23 C22 H22 119.7 . . ? C22 C23 H23 119.1 . . ? C22 C23 C24 121.8(2) . . ? C24 C23 H23 119.1 . . ? C23 C24 C27 120.5(2) . . ? C25 C24 C23 116.9(2) . . ? C25 C24 C27 122.5(2) . . ? C24 C25 H25 118.9 . . ? C24 C25 C26 122.3(2) . . ? C26 C25 H25 118.9 . . ? C21 C26 H26 119.9 . . ? C25 C26 C21 120.2(2) . . ? C25 C26 H26 119.9 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27B 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? _shelx_res_file ; TITL cr2_010_a.res in Pbca ajgi831_2_1.res created by SHELXL-2017/1 at 10:06:52 on 06-Jul-2018 REM Old TITL cr2_010 in Pbca REM SHELXT solution in Pbca REM R1 0.219, Rweak 0.004, Alpha 0.036, Orientation as input REM Formula found by SHELXT: C25 N2 CELL 1.54184 21.30209 7.718084 23.544368 90 90 90 ZERR 8 0.001025 0.000402 0.001187 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 UNIT 200 192 16 L.S. 4 0 0 PLAN 20 SIZE 0.02 0.067 0.466 TEMP -93 BOND $H list 4 fmap 2 53 acta REM REM REM WGHT 0.070800 EXTI 0.000404 FVAR 1.99974 N1 3 0.201433 0.275189 0.302863 11.00000 0.02713 0.03798 = 0.03368 0.00111 -0.00089 0.00014 N4 3 0.256985 0.279962 0.196891 11.00000 0.03020 0.04328 = 0.03130 -0.00053 -0.00235 0.00103 C2 1 0.165120 0.341972 0.254973 11.00000 0.03074 0.03992 = 0.03979 0.00109 -0.00160 0.00097 AFIX 23 H2A 2 0.168784 0.469774 0.253596 11.00000 -1.20000 H2B 2 0.120268 0.312257 0.260105 11.00000 -1.20000 AFIX 0 C3 1 0.188743 0.265313 0.199761 11.00000 0.02890 0.04524 = 0.03779 0.00258 -0.00432 -0.00019 AFIX 23 H3A 2 0.176379 0.141884 0.197348 11.00000 -1.20000 H3B 2 0.169608 0.327408 0.167296 11.00000 -1.20000 AFIX 0 C5 1 0.294011 0.243716 0.150319 11.00000 0.03710 0.04050 = 0.03221 0.00063 0.00028 0.00243 C6 1 0.276371 0.204159 0.094892 11.00000 0.04125 0.06025 = 0.03563 -0.00209 -0.00438 0.00033 AFIX 43 H6 2 0.233419 0.197838 0.084234 11.00000 -1.20000 AFIX 0 C7 1 0.323622 0.174478 0.056017 11.00000 0.05374 0.06219 = 0.03217 -0.00497 -0.00040 0.00099 AFIX 43 H7 2 0.312709 0.146836 0.017959 11.00000 -1.20000 AFIX 0 C8 1 0.387357 0.183862 0.070965 11.00000 0.05010 0.05051 = 0.03596 0.00291 0.00543 0.00450 C9 1 0.436953 0.154004 0.026063 11.00000 0.05867 0.07734 = 0.04244 -0.00059 0.01233 0.01005 AFIX 137 H9A 2 0.478097 0.187968 0.040991 11.00000 -1.50000 H9B 2 0.427178 0.223647 -0.007598 11.00000 -1.50000 H9C 2 0.437724 0.031046 0.015700 11.00000 -1.50000 AFIX 0 C10 1 0.404005 0.222904 0.126432 11.00000 0.03909 0.04378 = 0.03765 0.00362 0.00244 0.00263 AFIX 43 H10 2 0.447059 0.229883 0.136703 11.00000 -1.20000 AFIX 0 C11 1 0.357310 0.252176 0.167495 11.00000 0.03455 0.03524 = 0.03405 0.00399 -0.00018 0.00202 C12 1 0.357336 0.291540 0.227285 11.00000 0.02982 0.03420 = 0.03301 0.00240 0.00123 -0.00101 C13 1 0.410905 0.300108 0.266650 11.00000 0.02882 0.03744 = 0.03378 0.00247 0.00223 -0.00333 C14 1 0.462070 0.187269 0.261535 11.00000 0.03110 0.04381 = 0.04176 0.00423 0.00485 -0.00091 AFIX 43 H14 2 0.463822 0.108605 0.230542 11.00000 -1.20000 AFIX 0 C15 1 0.509982 0.188992 0.300989 11.00000 0.03183 0.05953 = 0.04937 0.00942 -0.00026 0.00100 AFIX 43 H15 2 0.544265 0.111221 0.296992 11.00000 -1.20000 AFIX 0 C16 1 0.508509 0.302967 0.346292 11.00000 0.03573 0.07660 = 0.04421 0.01012 -0.00890 -0.00793 AFIX 43 H16 2 0.541496 0.303027 0.373446 11.00000 -1.20000 AFIX 0 C17 1 0.458829 0.416717 0.351858 11.00000 0.04180 0.06248 = 0.03766 -0.00377 -0.00079 -0.01079 AFIX 43 H17 2 0.457650 0.495172 0.382930 11.00000 -1.20000 AFIX 0 C18 1 0.410730 0.416755 0.312281 11.00000 0.03576 0.04473 = 0.03959 -0.00217 0.00288 -0.00473 AFIX 43 H18 2 0.377159 0.496935 0.316112 11.00000 -1.20000 AFIX 0 C19 1 0.295084 0.305651 0.242986 11.00000 0.03208 0.03127 = 0.03393 0.00027 -0.00305 -0.00205 C20 1 0.266682 0.338237 0.299809 11.00000 0.02791 0.03935 = 0.03528 -0.00301 0.00077 -0.00342 AFIX 23 H20A 2 0.292089 0.279442 0.329273 11.00000 -1.20000 H20B 2 0.267432 0.464152 0.307802 11.00000 -1.20000 AFIX 0 C21 1 0.174968 0.301050 0.358074 11.00000 0.03301 0.03462 = 0.03810 -0.00358 0.00187 -0.00527 C22 1 0.203377 0.219969 0.404206 11.00000 0.03942 0.04753 = 0.03671 -0.00213 -0.00070 0.00144 AFIX 43 H22 2 0.239817 0.151184 0.398489 11.00000 -1.20000 AFIX 0 C23 1 0.179061 0.238677 0.458129 11.00000 0.04760 0.05291 = 0.03594 -0.00120 -0.00115 -0.00172 AFIX 43 H23 2 0.199287 0.182421 0.489002 11.00000 -1.20000 AFIX 0 C24 1 0.125658 0.337790 0.468580 11.00000 0.04688 0.05584 = 0.03977 -0.00509 0.00959 -0.00534 C25 1 0.097714 0.415696 0.422370 11.00000 0.04458 0.06512 = 0.05088 -0.00360 0.01059 0.00998 AFIX 43 H25 2 0.060763 0.482381 0.428070 11.00000 -1.20000 AFIX 0 C26 1 0.121666 0.400112 0.367853 11.00000 0.04130 0.05387 = 0.04263 0.00159 0.00493 0.00870 AFIX 43 H26 2 0.101551 0.457366 0.337119 11.00000 -1.20000 AFIX 0 C27 1 0.100700 0.357551 0.528090 11.00000 0.06288 0.08179 = 0.04491 -0.00720 0.01293 -0.00094 AFIX 137 H27A 2 0.107198 0.249410 0.549096 11.00000 -1.50000 H27B 2 0.055735 0.384016 0.526625 11.00000 -1.50000 H27C 2 0.122930 0.452084 0.547265 11.00000 -1.50000 AFIX 0 HKLF 4 REM cr2_010_a.res in Pbca REM R1 = 0.0549 for 2423 Fo > 4sig(Fo) and 0.0881 for all 3621 data REM 247 parameters refined using 0 restraints END WGHT 0.0708 0.0000 REM Highest difference peak 0.192, deepest hole -0.207, 1-sigma level 0.049 Q1 1 0.0593 0.2580 0.5416 11.00000 0.05 0.19 Q2 1 0.2069 0.1512 0.2994 11.00000 0.05 0.18 Q3 1 0.3208 0.2741 0.2407 11.00000 0.05 0.18 Q4 1 0.1186 0.1677 0.3566 11.00000 0.05 0.17 Q5 1 0.4801 0.3010 0.3616 11.00000 0.05 0.16 Q6 1 0.3447 0.6511 0.3174 11.00000 0.05 0.16 Q7 1 0.4593 0.1895 0.3606 11.00000 0.05 0.15 Q8 1 0.1266 0.2927 0.3572 11.00000 0.05 0.15 Q9 1 0.1229 0.1959 0.2782 11.00000 0.05 0.14 Q10 1 0.4226 0.2056 0.2752 11.00000 0.05 0.14 Q11 1 0.4593 0.2975 0.1424 11.00000 0.05 0.14 Q12 1 0.3814 0.2947 0.2424 11.00000 0.05 0.14 Q13 1 0.1185 0.2634 0.1806 11.00000 0.05 0.14 Q14 1 0.2567 0.6052 0.3406 11.00000 0.05 0.14 Q15 1 0.5213 0.3334 0.2544 11.00000 0.05 0.14 Q16 1 0.1184 0.2394 0.3753 11.00000 0.05 0.14 Q17 1 0.5261 0.2687 0.4048 11.00000 0.05 0.13 Q18 1 0.1155 0.2427 0.2596 11.00000 0.05 0.13 Q19 1 0.0839 0.2453 0.2392 11.00000 0.05 0.13 Q20 1 0.3376 0.2394 0.1606 11.00000 0.05 0.13 ; _shelx_res_checksum 98958 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.568 _oxdiff_exptl_absorpt_empirical_full_min 0.712