# Supplementary Information (SI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2024 ####################################################################### # # 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_2_211_1 _database_code_depnum_ccdc_archive 'CCDC 2335728' loop_ _audit_author_name _audit_author_address 'zurong Xu' ;South China University of Technology China ; _audit_update_record ; 2024-02-27 deposited with the CCDC. 2024-11-18 downloaded from the CCDC. ; _audit_creation_date 2023-04-01 _audit_creation_method ; Olex2 1.5-beta (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439) ; _shelx_SHELXL_version_number 2018/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C14 H13 Br O3' _chemical_formula_sum 'C14 H13 Br O3' _chemical_formula_weight 309.15 _chemical_melting_point ? 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' Br Br -0.6763 1.2805 '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 monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.5459(6) _cell_length_b 7.4134(4) _cell_length_c 27.118(3) _cell_angle_alpha 90 _cell_angle_beta 96.115(9) _cell_angle_gamma 90 _cell_volume 1308.48(19) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2753 _cell_measurement_temperature 149.99(10) _cell_measurement_theta_max 70.9200 _cell_measurement_theta_min 3.2270 _shelx_estimated_absorpt_T_max 0.726 _shelx_estimated_absorpt_T_min 0.607 _exptl_absorpt_coefficient_mu 4.273 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.48611 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour 'light colourless' _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description prism _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_av_unetI/netI 0.1447 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_number 2308 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 66.568 _diffrn_reflns_theta_max 66.568 _diffrn_reflns_theta_min 3.278 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 149.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 -117.00 -8.00 1.00 1.00 -- -40.92 -77.00 0.00 109 2 \w -115.00 -17.00 1.00 1.00 -- -40.92 -37.00-150.00 98 3 \w 23.00 97.00 1.00 1.00 -- 40.92-125.00 30.00 74 4 \w 17.00 92.00 1.00 1.00 -- 40.92-117.00-150.00 75 5 \w 17.00 115.00 1.00 1.00 -- 40.92 37.00 120.00 98 6 \w 81.00 178.00 1.00 1.50 -- 106.95 45.00 -90.00 97 7 \w 34.00 121.00 1.00 1.50 -- 106.95-125.00 150.00 87 8 \w 32.00 74.00 1.00 1.50 -- 106.95 -15.00-150.00 42 9 \w 42.00 86.00 1.00 1.50 -- 106.95 -30.00 -60.00 44 10 \w 100.00 135.00 1.00 1.50 -- 106.95 -30.00 120.00 35 11 \w 106.00 134.00 1.00 1.50 -- 106.95 -30.00 -60.00 28 12 \w 126.00 178.00 1.00 1.50 -- 106.95 125.00 30.00 52 13 \w 32.00 95.00 1.00 1.50 -- 106.95 -30.00 120.00 63 14 \w 81.00 149.00 1.00 1.50 -- 106.95 45.00 120.00 68 15 \w 87.00 144.00 1.00 1.50 -- 106.95 -15.00-150.00 57 16 \w 35.00 136.00 1.00 1.50 -- 106.95 -61.00 120.00 101 17 \w 82.00 109.00 1.00 1.50 -- 106.95 -94.00 -60.00 27 18 \w 32.00 140.00 1.00 1.50 -- 106.95 -77.00 -60.00 108 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0742923000 _diffrn_orient_matrix_UB_12 0.0579478000 _diffrn_orient_matrix_UB_13 0.0535210000 _diffrn_orient_matrix_UB_21 0.0124809000 _diffrn_orient_matrix_UB_22 0.1972671000 _diffrn_orient_matrix_UB_23 -0.0172792000 _diffrn_orient_matrix_UB_31 -0.2242336000 _diffrn_orient_matrix_UB_32 0.0301412000 _diffrn_orient_matrix_UB_33 0.0102624000 _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 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1980 _reflns_number_total 2308 _reflns_special_details ; _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 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _refine_diff_density_max 3.426 _refine_diff_density_min -1.543 _refine_diff_density_rms 0.439 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 2.595 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 2308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1251 _refine_ls_R_factor_gt 0.1137 _refine_ls_restrained_S_all 2.595 _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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3452 _refine_ls_wR_factor_ref 0.3523 _refine_special_details ; Refined as a 2-component twin. ; _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.712(7) 0.288(7) 2. 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 3.a Ternary CH refined with riding coordinates: C7(H7) 3.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C10(H10A,H10B) 3.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C11(H11) 3.d Idealised Me refined as rotating group: C14(H14A,H14B,H14C) ; _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 Br1 Br 0.8435(2) 0.19899(15) 0.54635(4) 0.0615(4) Uani 1 1 d . . . A 1 O1 O 0.1860(11) 0.5075(8) 0.2032(2) 0.0422(16) Uani 1 1 d . . . . . O2 O 0.1769(15) 0.2269(11) 0.1726(3) 0.062(2) Uani 1 1 d . . . . . O3 O -0.2383(12) 0.4290(10) 0.1929(3) 0.053(2) Uani 1 1 d . . . . . C1 C 0.4399(15) 0.4016(12) 0.4049(3) 0.042(2) Uani 1 1 d . . . . . C2 C 0.6508(15) 0.4526(14) 0.4138(4) 0.046(2) Uani 1 1 d . . . . . H2 H 0.710064 0.527383 0.390652 0.055 Uiso 1 1 calc R U . . . C3 C 0.7662(16) 0.3951(12) 0.4549(3) 0.044(2) Uani 1 1 d . . . . . H3 H 0.906332 0.429443 0.461187 0.053 Uiso 1 1 calc R U . . . C4 C 0.6754(16) 0.2832(11) 0.4882(4) 0.043(2) Uani 1 1 d . . . . . C5 C 0.4760(15) 0.2371(11) 0.4810(3) 0.039(2) Uani 1 1 d . . . . . H5 H 0.418572 0.165640 0.505138 0.046 Uiso 1 1 calc R U . . . C6 C 0.354(2) 0.2911(13) 0.4395(4) 0.051(3) Uani 1 1 d . . . . . H6 H 0.214420 0.254737 0.434214 0.061 Uiso 1 1 calc R U . . . C7 C 0.3141(19) 0.4750(10) 0.3604(3) 0.049(3) Uani 1 1 d . . . . . H7 H 0.274446 0.603039 0.365994 0.059 Uiso 1 1 calc R U . . . C8 C 0.3986(17) 0.4530(14) 0.3081(4) 0.047(3) Uani 1 1 d . . . . . H8A H 0.456620 0.565144 0.295475 0.057 Uiso 1 1 calc R U . . . H8B H 0.494319 0.350349 0.306292 0.057 Uiso 1 1 calc R U . . . C9 C 0.1887(16) 0.4148(11) 0.2868(3) 0.042(2) Uani 1 1 d . . . . . C10 C 0.1266(16) 0.3652(13) 0.3361(4) 0.047(2) Uani 1 1 d . . . . . H10A H 0.134756 0.234275 0.343194 0.056 Uiso 1 1 calc R U . . . H10B H -0.008157 0.414943 0.342655 0.056 Uiso 1 1 calc R U . . . C11 C -0.1340(15) 0.4089(11) 0.2340(4) 0.040(2) Uani 1 1 d . . . . . H11 H -0.203426 0.373370 0.261480 0.049 Uiso 1 1 calc R U . . . C12 C 0.0769(15) 0.4354(13) 0.2419(3) 0.042(2) Uani 1 1 d . . . . . C13 C 0.2157(15) 0.3818(11) 0.1681(3) 0.040(2) Uani 1 1 d . . . . . C14 C 0.3118(15) 0.4677(13) 0.1253(3) 0.044(2) Uani 1 1 d . . . . . H14A H 0.254609 0.588686 0.119082 0.066 Uiso 1 1 calc R U . . . H14B H 0.282101 0.393454 0.095488 0.066 Uiso 1 1 calc R U . . . H14C H 0.460887 0.476241 0.133687 0.066 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0742(8) 0.0517(6) 0.0550(7) 0.0070(4) -0.0092(6) 0.0034(5) O1 0.056(4) 0.038(3) 0.034(3) -0.006(2) 0.009(3) -0.002(3) O2 0.076(5) 0.062(4) 0.053(4) -0.003(3) 0.030(4) 0.001(4) O3 0.052(4) 0.060(4) 0.048(4) 0.010(3) 0.003(3) 0.002(3) C1 0.043(5) 0.042(4) 0.042(4) 0.004(4) 0.016(4) -0.002(4) C2 0.040(5) 0.050(4) 0.051(5) 0.008(4) 0.021(4) -0.003(4) C3 0.044(5) 0.046(4) 0.041(4) -0.009(4) 0.001(4) 0.000(4) C4 0.051(5) 0.042(4) 0.039(4) -0.001(4) 0.016(4) 0.012(4) C5 0.051(5) 0.026(3) 0.042(4) 0.003(3) 0.019(4) 0.000(3) C6 0.063(6) 0.049(5) 0.041(5) -0.002(4) 0.003(5) 0.000(4) C7 0.083(7) 0.015(3) 0.047(5) -0.005(3) -0.006(5) -0.001(4) C8 0.051(5) 0.044(4) 0.050(5) -0.001(4) 0.018(4) -0.004(4) C9 0.048(5) 0.039(4) 0.039(4) -0.002(3) 0.009(4) 0.004(4) C10 0.043(5) 0.043(4) 0.053(5) -0.003(4) -0.001(4) -0.001(4) C11 0.039(4) 0.031(3) 0.055(5) 0.002(3) 0.022(4) 0.003(3) C12 0.040(4) 0.045(4) 0.042(4) -0.005(4) 0.014(4) 0.005(4) C13 0.042(5) 0.032(4) 0.047(5) -0.001(3) -0.001(4) -0.013(3) C14 0.047(5) 0.044(4) 0.043(4) 0.002(4) 0.016(4) -0.004(4) _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 Br1 C4 1.927(10) . ? O1 C12 1.434(12) . ? O1 C13 1.361(11) . ? O2 C13 1.185(12) . ? O3 C11 1.254(12) . ? C1 C2 1.427(14) . ? C1 C6 1.408(15) . ? C1 C7 1.489(13) . ? C2 H2 0.9500 . ? C2 C3 1.347(13) . ? C3 H3 0.9500 . ? C3 C4 1.405(14) . ? C4 C5 1.343(15) . ? C5 H5 0.9500 . ? C5 C6 1.367(14) . ? C6 H6 0.9500 . ? C7 H7 1.0000 . ? C7 C8 1.586(14) . ? C7 C10 1.560(14) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.460(14) . ? C9 C10 1.483(14) . ? C9 C12 1.361(13) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11 0.9500 . ? C11 C12 1.388(14) . ? C13 C14 1.518(13) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 C13 O1 C12 112.1(7) . . ? C2 C1 C7 118.8(9) . . ? C6 C1 C2 119.3(9) . . ? C6 C1 C7 121.9(10) . . ? C1 C2 H2 119.9 . . ? C3 C2 C1 120.2(9) . . ? C3 C2 H2 119.9 . . ? C2 C3 H3 120.6 . . ? C2 C3 C4 118.8(10) . . ? C4 C3 H3 120.6 . . ? C3 C4 Br1 118.3(8) . . ? C5 C4 Br1 119.9(7) . . ? C5 C4 C3 121.8(9) . . ? C4 C5 H5 119.4 . . ? C4 C5 C6 121.2(10) . . ? C6 C5 H5 119.4 . . ? C1 C6 H6 120.6 . . ? C5 C6 C1 118.7(11) . . ? C5 C6 H6 120.6 . . ? C1 C7 H7 110.7 . . ? C1 C7 C8 118.2(9) . . ? C1 C7 C10 119.7(8) . . ? C8 C7 H7 110.7 . . ? C10 C7 H7 110.7 . . ? C10 C7 C8 84.3(7) . . ? C7 C8 H8A 113.9 . . ? C7 C8 H8B 113.9 . . ? H8A C8 H8B 111.1 . . ? C9 C8 C7 88.3(8) . . ? C9 C8 H8A 113.9 . . ? C9 C8 H8B 113.9 . . ? C8 C9 C10 91.6(8) . . ? C12 C9 C8 136.5(10) . . ? C12 C9 C10 131.4(10) . . ? C7 C10 H10A 113.9 . . ? C7 C10 H10B 113.9 . . ? C9 C10 C7 88.5(8) . . ? C9 C10 H10A 113.9 . . ? C9 C10 H10B 113.9 . . ? H10A C10 H10B 111.1 . . ? O3 C11 H11 118.0 . . ? O3 C11 C12 124.0(9) . . ? C12 C11 H11 118.0 . . ? C9 C12 O1 115.8(9) . . ? C9 C12 C11 123.6(9) . . ? C11 C12 O1 120.3(8) . . ? O1 C13 C14 110.5(7) . . ? O2 C13 O1 122.9(9) . . ? O2 C13 C14 126.6(9) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br1 C4 C5 C6 -178.4(7) . . . . ? O3 C11 C12 O1 6.7(14) . . . . ? O3 C11 C12 C9 179.4(9) . . . . ? C1 C2 C3 C4 0.6(15) . . . . ? C1 C7 C8 C9 140.4(8) . . . . ? C1 C7 C10 C9 -138.7(9) . . . . ? C2 C1 C6 C5 0.5(14) . . . . ? C2 C1 C7 C8 52.3(11) . . . . ? C2 C1 C7 C10 152.4(10) . . . . ? C2 C3 C4 Br1 179.1(7) . . . . ? C2 C3 C4 C5 -2.1(14) . . . . ? C3 C4 C5 C6 2.8(14) . . . . ? C4 C5 C6 C1 -2.0(15) . . . . ? C6 C1 C2 C3 0.1(15) . . . . ? C6 C1 C7 C8 -130.9(10) . . . . ? C6 C1 C7 C10 -30.8(14) . . . . ? C7 C1 C2 C3 177.0(9) . . . . ? C7 C1 C6 C5 -176.3(9) . . . . ? C7 C8 C9 C10 -20.7(7) . . . . ? C7 C8 C9 C12 151.7(11) . . . . ? C8 C7 C10 C9 -19.4(7) . . . . ? C8 C9 C10 C7 21.0(7) . . . . ? C8 C9 C12 O1 2.5(16) . . . . ? C8 C9 C12 C11 -170.5(10) . . . . ? C10 C7 C8 C9 19.7(7) . . . . ? C10 C9 C12 O1 172.3(9) . . . . ? C10 C9 C12 C11 -0.7(16) . . . . ? C12 O1 C13 O2 -8.4(13) . . . . ? C12 O1 C13 C14 174.2(7) . . . . ? C12 C9 C10 C7 -152.0(10) . . . . ? C13 O1 C12 C9 109.8(9) . . . . ? C13 O1 C12 C11 -77.0(10) . . . . ? _shelx_res_file ; TITL x2r=2-211-1_a.res in P2(1)/c 2_211_1.res created by SHELXL-2018/3 at 15:55:55 on 01-Apr-2023 REM Old TITL X2R=2-211-1 in P2(1) REM SHELXT solution in P2(1)/c: R1 0.294, Rweak 0.436, Alpha 0.220 REM 3.179 for 212 systematic absences, Orientation as input REM Formula found by SHELXT: C10 N4 O3 Br CELL 1.54184 6.5459 7.4134 27.118 90 96.115 90 ZERR 4 0.0006 0.0004 0.0025 0 0.009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br O UNIT 56 52 4 12 L.S. 20 PLAN 2 SIZE 0.08 0.12 0.13 TEMP -120 CONF BOND LIST 4 MORE -1 BOND $H fmap 2 53 acta MERG 0 SHEL 999 0.84 REM REM REM WGHT 0.200000 BASF 0.28775 FVAR 10.73359 PART 1 BR1 3 0.843492 0.198992 0.546346 11.00000 0.07419 0.05171 = 0.05502 0.00701 -0.00921 0.00343 PART 0 O1 4 0.185955 0.507475 0.203203 11.00000 0.05573 0.03750 = 0.03439 -0.00572 0.00892 -0.00168 O2 4 0.176914 0.226945 0.172629 11.00000 0.07622 0.06190 = 0.05252 -0.00343 0.02965 0.00056 O3 4 -0.238344 0.428952 0.192862 11.00000 0.05176 0.06013 = 0.04765 0.00980 0.00321 0.00153 C1 1 0.439896 0.401641 0.404889 11.00000 0.04312 0.04239 = 0.04196 0.00396 0.01620 -0.00164 C2 1 0.650822 0.452637 0.413777 11.00000 0.03974 0.05043 = 0.05149 0.00788 0.02142 -0.00339 AFIX 43 H2 2 0.710064 0.527383 0.390652 11.00000 -1.20000 AFIX 0 C3 1 0.766178 0.395054 0.454881 11.00000 0.04418 0.04623 = 0.04101 -0.00855 0.00134 0.00009 AFIX 43 H3 2 0.906332 0.429443 0.461187 11.00000 -1.20000 AFIX 0 C4 1 0.675358 0.283219 0.488242 11.00000 0.05056 0.04202 = 0.03852 -0.00069 0.01628 0.01174 C5 1 0.475997 0.237091 0.481007 11.00000 0.05134 0.02559 = 0.04235 0.00324 0.01947 -0.00031 AFIX 43 H5 2 0.418572 0.165640 0.505138 11.00000 -1.20000 AFIX 0 C6 1 0.354192 0.291106 0.439538 11.00000 0.06252 0.04863 = 0.04064 -0.00152 0.00324 -0.00044 AFIX 43 H6 2 0.214420 0.254737 0.434214 11.00000 -1.20000 AFIX 0 C7 1 0.314123 0.474981 0.360412 11.00000 0.08258 0.01497 = 0.04701 -0.00502 -0.00630 -0.00092 AFIX 13 H7 2 0.274446 0.603039 0.365994 11.00000 -1.20000 AFIX 0 C8 1 0.398611 0.452973 0.308076 11.00000 0.05096 0.04410 = 0.04963 -0.00060 0.01804 -0.00384 AFIX 23 H8A 2 0.456620 0.565144 0.295475 11.00000 -1.20000 H8B 2 0.494319 0.350349 0.306292 11.00000 -1.20000 AFIX 0 C9 1 0.188660 0.414830 0.286801 11.00000 0.04823 0.03934 = 0.03888 -0.00187 0.00895 0.00397 C10 1 0.126620 0.365192 0.336052 11.00000 0.04331 0.04279 = 0.05332 -0.00299 -0.00117 -0.00063 AFIX 23 H10A 2 0.134756 0.234275 0.343194 11.00000 -1.20000 H10B 2 -0.008157 0.414943 0.342655 11.00000 -1.20000 AFIX 0 C11 1 -0.133978 0.408877 0.234022 11.00000 0.03908 0.03148 = 0.05461 0.00204 0.02209 0.00258 AFIX 43 H11 2 -0.203426 0.373370 0.261480 11.00000 -1.20000 AFIX 0 C12 1 0.076883 0.435397 0.241894 11.00000 0.03999 0.04502 = 0.04190 -0.00475 0.01421 0.00518 C13 1 0.215677 0.381794 0.168109 11.00000 0.04161 0.03187 = 0.04677 -0.00114 -0.00077 -0.01253 C14 1 0.311841 0.467653 0.125298 11.00000 0.04718 0.04422 = 0.04271 0.00191 0.01615 -0.00353 AFIX 137 H14A 2 0.254609 0.588686 0.119082 11.00000 -1.50000 H14B 2 0.282101 0.393454 0.095488 11.00000 -1.50000 H14C 2 0.460887 0.476241 0.133687 11.00000 -1.50000 AFIX 0 HKLF 5 REM x2r=2-211-1_a.res in P2(1)/c REM wR2 = 0.3523, GooF = S = 2.595, Restrained GooF = 2.595 for all data REM R1 = 0.1137 for 1980 Fo > 4sig(Fo) and 0.1251 for all 2308 data REM 165 parameters refined using 0 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 3.426, deepest hole -1.543, 1-sigma level 0.439 Q1 1 0.9882 0.1994 0.5440 11.00000 0.05 3.43 Q2 1 0.8494 0.2940 0.5455 11.00000 0.05 2.00 ; _shelx_res_checksum 2077 _shelx_hkl_file ; 1 0 0 160024 5783 1 2 0 0 2348415 1364641 1 3 0 0 1394040 21195 1 4 0 0 149964 12433 1 -5 0 4 54775 3919 -2 5 0 0 54775 3919 1 6 0 0 50904 3441 1 7 0 0 13110 3879 1 1 1 0 1267509 421106 1 2 1 0 375603 169693 1 3 1 0 7089 3011 1 4 1 0 30888 3998 1 -5 -1 4 66762 2740 -2 5 1 0 66762 2740 1 6 1 0 5878 1179 1 7 1 0 18797 2716 1 0 -2 0 40135 1864 -2 0 2 0 40135 1864 1 1 2 0 390027 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13955 1776 1 3 1 21 35030 2907 1 4 1 21 -199 526 1 5 1 21 1346 438 1 -6 2 21 10004 1290 1 -5 2 21 12847 7973 1 -4 2 21 7702 1497 1 -3 2 21 3919 1689 1 -2 2 21 8491 1274 1 -1 2 21 21250 2055 1 0 2 21 526 621 1 1 2 21 64333 3250 1 2 2 21 6746 1163 1 3 2 21 1633 733 1 4 2 21 16344 2166 1 5 2 21 1585 406 1 -6 3 21 4030 1027 1 -5 3 21 7527 4683 1 -4 3 21 23345 4803 1 -3 3 21 8156 1537 1 -2 3 21 31772 9622 1 -1 3 21 14847 1951 1 0 3 21 139546 5344 1 1 3 21 4205 980 1 2 3 21 13413 1697 1 3 3 21 18272 1880 1 4 3 21 21760 2350 1 5 3 21 1434 510 1 -5 4 21 2023 948 1 -4 4 21 32887 3544 1 -3 4 21 3975 1832 1 -2 4 21 25297 2366 1 -1 4 21 4110 980 1 0 4 21 3640 948 1 1 4 21 35022 2517 1 2 4 21 70641 3767 1 3 4 21 2103 677 1 4 4 21 6029 1474 1 -5 5 21 629 550 1 -4 5 21 19618 2461 1 -3 5 21 12170 3282 1 -2 5 21 7814 2804 1 -1 5 21 9454 1410 1 0 5 21 45583 3035 1 1 5 21 3393 868 1 2 5 21 9701 1410 1 3 5 21 22437 1784 1 4 5 21 -175 446 1 -4 6 21 12186 1720 1 -3 6 21 1179 685 1 -2 6 21 4460 956 1 -1 6 21 12322 1418 1 0 6 21 255 422 1 1 6 21 18152 1601 1 2 6 21 11685 1657 1 -2 7 21 5090 1529 1 -1 7 21 10554 1354 1 0 7 21 27750 2859 1 1 7 21 5982 1227 1 -6 0 22 2007 1418 1 -5 0 22 446 1083 1 -4 0 22 2111 1697 1 -3 0 22 1505 1928 1 -2 0 22 11517 2541 1 -1 0 22 7415 1776 1 0 0 22 152799 7782 1 1 0 22 81537 5647 1 2 0 22 43194 7137 1 3 0 22 37539 3505 1 4 0 22 36766 3106 1 5 0 22 502 518 1 -6 1 22 12585 7009 1 -5 1 22 5902 3138 1 -4 1 22 41585 4205 1 -3 1 22 2350 1243 1 -2 1 22 76432 3911 1 -1 1 22 177419 7065 1 0 1 22 5137 1266 1 1 1 22 55548 3274 1 2 1 22 74855 4110 1 3 1 22 11557 1657 1 4 1 22 14440 1545 1 5 1 22 24795 1394 1 -6 2 22 5759 1505 1 -5 2 22 7909 8124 1 -4 2 22 1912 980 1 -3 2 22 33301 15109 1 -2 2 22 60032 4381 1 -1 2 22 72847 4588 1 0 2 22 57587 3704 1 1 2 22 35627 2748 1 2 2 22 2700 765 1 3 2 22 39403 2350 1 4 2 22 24038 2477 1 5 2 22 1497 462 1 -6 3 22 3250 852 1 -5 3 22 16687 9040 1 -4 3 22 11135 7933 1 -3 3 22 12011 7033 1 -2 3 22 12664 3409 1 -1 3 22 4994 1147 1 0 3 22 14018 1625 1 1 3 22 9789 1282 1 2 3 22 2437 812 1 3 3 22 2254 653 1 4 3 22 5129 1075 1 -5 4 22 1187 749 1 -4 4 22 3990 1250 1 -3 4 22 9048 8857 1 -2 4 22 3839 1004 1 -1 4 22 26985 2063 1 0 4 22 327 605 1 1 4 22 47901 3138 1 2 4 22 2533 820 1 3 4 22 271 478 1 4 4 22 2939 765 1 -5 5 22 8196 1681 1 -4 5 22 1545 820 1 -3 5 22 27877 21800 1 -2 5 22 581 605 1 -1 5 22 3242 844 1 0 5 22 1027 597 1 1 5 22 7200 1314 1 2 5 22 -143 462 1 3 5 22 1912 550 1 -3 6 22 3895 2692 1 -2 6 22 2445 733 1 -1 6 22 9821 1163 1 0 6 22 1967 613 1 1 6 22 6691 1394 1 2 6 22 956 510 1 -6 1 23 3170 597 1 -5 1 23 7097 2190 1 -4 1 23 1545 876 1 -3 1 23 11573 2374 1 -2 1 23 15396 2143 1 -1 1 23 46690 4835 1 0 1 23 159 1012 1 1 1 23 44970 3090 1 2 1 23 21242 2111 1 3 1 23 2445 812 1 4 1 23 9574 1505 1 5 1 23 382 335 1 -6 2 23 3775 765 1 -5 2 23 20518 10864 1 -4 2 23 5480 1211 1 -3 2 23 10147 4755 1 -2 2 23 13477 4221 1 -1 2 23 34377 4333 1 0 2 23 8507 2111 1 1 2 23 10131 1497 1 2 2 23 23313 1935 1 3 2 23 5599 996 1 4 2 23 1840 677 1 5 2 23 6077 1290 1 -6 3 23 2294 1004 1 -5 3 23 2573 860 1 -4 3 23 4413 1322 1 -3 3 23 20709 3528 1 -2 3 23 12736 1697 1 -1 3 23 8228 1474 1 0 3 23 72131 4030 1 1 3 23 52831 3377 1 2 3 23 2772 820 1 3 3 23 15197 1330 1 4 3 23 11223 1442 1 -5 4 23 1880 781 1 -4 4 23 34050 3329 1 -3 4 23 1282 1123 1 -2 4 23 20478 2310 1 -1 4 23 66388 3385 1 0 4 23 11183 1386 1 1 4 23 21466 2071 1 2 4 23 29781 1951 1 3 4 23 167 486 1 4 4 23 3536 733 1 -4 5 23 1282 701 1 -3 5 23 4373 1521 1 -2 5 23 7168 1712 1 -1 5 23 5775 1012 1 0 5 23 67344 3401 1 1 5 23 11254 1505 1 2 5 23 8666 1561 1 3 5 23 8124 884 1 -3 6 23 2931 1195 1 -2 6 23 14122 1935 1 -1 6 23 10402 1091 1 0 6 23 21067 1784 1 1 6 23 2867 828 1 2 6 23 46491 2708 1 -6 0 24 14249 11780 1 -5 0 24 -1290 1290 1 -4 0 24 3035 1609 1 -3 0 24 1386 1904 1 -2 0 24 91031 28268 1 -1 0 24 13174 3959 1 0 0 24 146316 8825 1 1 0 24 103990 7543 1 2 0 24 5408 3090 1 3 0 24 20231 4126 1 4 0 24 38710 4452 1 5 0 24 613 542 1 -6 1 24 1489 1633 1 -5 1 24 9526 2828 1 -4 1 24 50681 20868 1 -3 1 24 36360 3927 1 -2 1 24 61625 20741 1 -1 1 24 63680 6523 1 0 1 24 22182 3321 1 1 1 24 3266 988 1 2 1 24 16248 1856 1 3 1 24 41258 2867 1 4 1 24 526 438 1 -6 2 24 5042 1067 1 -5 2 24 3648 900 1 -4 2 24 7758 5273 1 -3 2 24 5305 4245 1 -2 2 24 5098 1561 1 -1 2 24 10259 2286 1 0 2 24 9733 2238 1 1 2 24 30689 2501 1 2 2 24 4134 948 1 3 2 24 7630 1171 1 4 2 24 21067 1975 1 -5 3 24 8881 1601 1 -4 3 24 9701 1959 1 -3 3 24 15603 5241 1 -2 3 24 3202 1338 1 -1 3 24 55070 4277 1 0 3 24 44054 3059 1 1 3 24 7551 1330 1 2 3 24 27352 1943 1 3 3 24 13955 1346 1 4 3 24 143 478 1 -5 4 24 3624 1083 1 -4 4 24 6539 1466 1 -3 4 24 781 653 1 -2 4 24 6037 1394 1 -1 4 24 15715 1521 1 0 4 24 255 605 1 1 4 24 23178 1999 1 2 4 24 5145 1004 1 3 4 24 852 350 1 -4 5 24 2302 804 1 -3 5 24 14775 7208 1 -2 5 24 2238 1035 1 -1 5 24 5862 996 1 0 5 24 3823 924 1 1 5 24 5599 1553 1 2 5 24 2772 884 1 -2 6 24 4739 1497 1 -1 6 24 3616 804 1 0 6 24 4221 765 1 1 6 24 3903 844 1 -6 1 25 924 1697 1 -5 1 25 13851 10036 1 -4 1 25 303 589 1 -3 1 25 16551 2652 1 -2 1 25 14186 4333 1 -1 1 25 5018 1704 1 0 1 25 42389 3831 1 1 1 25 37937 2859 1 2 1 25 5727 1107 1 3 1 25 151 653 1 4 1 25 255 390 1 -5 2 25 3775 844 1 -4 2 25 7845 3122 1 -3 2 25 22079 13381 1 -2 2 25 13246 7527 1 -1 2 25 25281 3449 1 0 2 25 54799 5153 1 1 2 25 11143 1426 1 2 2 25 26738 1975 1 3 2 25 11693 1378 1 4 2 25 358 342 1 -5 3 25 6221 1258 1 -4 3 25 24277 2820 1 -3 3 25 1840 908 1 -2 3 25 7941 2119 1 -1 3 25 10880 1888 1 0 3 25 3728 956 1 1 3 25 22987 2063 1 2 3 25 14345 1378 1 3 3 25 3051 908 1 4 3 25 9287 1561 1 -4 4 25 7137 1386 1 -3 4 25 446 542 1 -2 4 25 17826 7766 1 -1 4 25 31358 2851 1 0 4 25 25034 2023 1 1 4 25 1697 605 1 2 4 25 16766 2055 1 3 4 25 13803 4174 1 -4 5 25 1131 781 1 -3 5 25 2644 884 1 -2 5 25 23616 14958 1 -1 5 25 9502 1099 1 0 5 25 22318 1920 1 1 5 25 43082 2222 1 2 5 25 1274 566 1 -5 0 26 342 733 1 -4 0 26 20717 17499 1 -3 0 26 239 1442 1 -2 0 26 37977 23688 1 -1 0 26 5950 2668 1 0 0 26 16 1808 1 1 0 26 6850 2923 1 2 0 26 48451 6659 1 3 0 26 1689 876 1 4 0 26 34353 3505 1 -5 1 26 7479 2732 1 -4 1 26 15356 2389 1 -3 1 26 2947 1258 1 -2 1 26 10060 5496 1 -1 1 26 80318 6683 1 0 1 26 71039 4914 1 1 1 26 17021 1959 1 2 1 26 17109 2071 1 3 1 26 32370 2971 1 4 1 26 988 486 1 -5 2 26 2477 860 1 -4 2 26 27471 3003 1 -3 2 26 2812 2143 1 -2 2 26 11326 10203 1 -1 2 26 15683 2788 1 0 2 26 1266 1027 1 1 2 26 68475 3369 1 2 2 26 17810 1776 1 3 2 26 605 573 1 4 2 26 8188 1091 1 -5 3 26 2533 844 1 -4 3 26 4221 1171 1 -3 3 26 12242 4285 1 -2 3 26 14958 6029 1 -1 3 26 15372 2087 1 0 3 26 15340 2095 1 1 3 26 12816 1410 1 2 3 26 159 414 1 3 3 26 15787 1553 1 -4 4 26 3441 956 1 -3 4 26 773 820 1 -2 4 26 3911 1673 1 -1 4 26 1171 645 1 0 4 26 2413 685 1 1 4 26 3329 669 1 2 4 26 4094 765 1 -3 5 26 8491 1832 1 -2 5 26 2047 1760 1 -1 5 26 25886 5679 1 0 5 26 175 382 1 1 5 26 1545 820 1 -5 1 27 27814 2549 1 -4 1 27 8435 1736 1 -3 1 27 48196 4142 1 -2 1 27 2127 1083 1 -1 1 27 30131 3927 1 0 1 27 9016 2151 1 1 1 27 8602 1577 1 2 1 27 10092 1537 1 3 1 27 510 526 1 4 1 27 1951 581 1 -5 2 27 1768 677 1 -4 2 27 2366 956 1 -3 2 27 8905 1266 1 -2 2 27 16464 4994 1 -1 2 27 44413 4381 1 0 2 27 59641 4237 1 1 2 27 5767 1027 1 2 2 27 4875 948 1 3 2 27 3751 1099 1 -4 3 27 12202 1752 1 -3 3 27 5934 3680 1 -2 3 27 16631 2740 1 -1 3 27 12927 1864 1 0 3 27 10020 1617 1 1 3 27 20621 1625 1 2 3 27 6085 908 1 3 3 27 -135 510 1 -4 4 27 2987 1179 1 -3 4 27 8738 4086 1 -2 4 27 9861 5687 1 -1 4 27 3720 1187 1 0 4 27 26252 1840 1 1 4 27 14377 1298 1 2 4 27 1617 1027 1 -2 5 27 3943 1298 1 -1 5 27 3234 884 1 0 5 27 1258 510 1 1 5 27 11095 2007 1 -5 0 28 -390 685 1 -4 0 28 39769 4875 1 -3 0 28 -844 1107 1 -2 0 28 66635 7511 1 -1 0 28 17610 4134 1 0 0 28 70283 8546 1 1 0 28 32067 5544 1 2 0 28 67989 4659 1 3 0 28 5464 1529 1 -5 1 28 709 940 1 -4 1 28 1163 828 1 -3 1 28 1561 1474 1 -2 1 28 5050 1545 1 -1 1 28 8746 2190 1 0 1 28 39522 4389 1 1 1 28 20119 3090 1 2 1 28 1489 677 1 3 1 28 21067 1665 1 -5 2 28 5878 1298 1 -4 2 28 23417 2445 1 -3 2 28 9311 4277 1 -2 2 28 19650 2206 1 -1 2 28 7909 1625 1 0 2 28 1322 749 1 1 2 28 2939 812 1 2 2 28 12601 1497 1 3 2 28 3417 804 1 -4 3 28 -32 605 1 -3 3 28 2437 884 1 -2 3 28 1442 852 1 -1 3 28 15333 1912 1 0 3 28 14600 1593 1 1 3 28 15420 1561 1 2 3 28 3544 1083 1 -3 4 28 5360 7535 1 -2 4 28 4142 1027 1 -1 4 28 9829 1625 1 0 4 28 422 518 1 1 4 28 2724 566 1 -1 5 28 7861 1266 1 -5 1 29 14871 2222 1 -4 1 29 -621 677 1 -3 1 29 19196 11414 1 -2 1 29 1920 1123 1 -1 1 29 18319 2867 1 0 1 29 1012 1020 1 1 1 29 9470 2103 1 2 1 29 2294 733 1 3 1 29 191 701 1 -4 2 29 526 534 1 -3 2 29 1418 1553 1 -2 2 29 10052 1967 1 -1 2 29 3043 1027 1 0 2 29 3441 1083 1 1 2 29 10490 1529 1 2 2 29 247 789 1 -4 3 29 12155 2031 1 -3 3 29 9080 6778 1 -2 3 29 6555 1394 1 -1 3 29 22668 2182 1 0 3 29 10968 1298 1 1 3 29 4859 844 1 -2 4 29 2055 773 1 -1 4 29 1673 757 1 0 4 29 23616 1856 1 -4 0 30 32234 3600 1 -3 0 30 32 876 1 -2 0 30 8515 2397 1 -1 0 30 454 1266 1 0 0 30 10729 3011 1 1 0 30 908 1147 1 2 0 30 7384 1434 1 -4 1 30 1561 1187 1 -3 1 30 2525 3274 1 -2 1 30 3417 1179 1 -1 1 30 8554 1951 1 0 1 30 33771 3656 1 1 1 30 30394 4198 1 2 1 30 7718 908 1 -4 2 30 9327 1792 1 -3 2 30 2708 1195 1 -2 2 30 7344 2127 1 -1 2 30 9128 1458 1 0 2 30 26284 2397 1 1 2 30 80 605 1 2 2 30 15102 1673 1 -2 3 30 20820 2254 1 -1 3 30 2206 1012 1 0 3 30 4779 956 1 1 3 30 12441 1784 1 -1 4 30 4906 1020 1 0 4 30 4046 1394 1 -3 1 31 613 884 1 -2 1 31 6714 1458 1 -1 1 31 21888 2684 1 0 1 31 3098 964 1 1 1 31 7065 1235 1 2 1 31 486 948 1 -2 2 31 7288 1394 1 -1 2 31 820 605 1 0 2 31 4898 1004 1 1 2 31 4054 1147 1 -2 3 31 1107 924 1 -1 3 31 14982 1800 1 0 3 31 18996 1625 1 -1 0 32 14456 2971 1 0 0 32 59259 6037 1 1 0 32 8594 2143 1 -2 1 32 5010 1426 1 -1 1 32 12792 1537 1 0 1 32 1298 605 1 1 1 32 16081 1943 1 -2 2 32 1704 916 1 -1 2 32 2015 677 1 0 2 32 20143 1697 1 1 2 32 2716 1243 1 -2 1 33 -382 573 1 -1 1 33 6961 1330 1 0 1 33 2605 693 1 ; _shelx_hkl_checksum 17862 _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 1.662 _oxdiff_exptl_absorpt_empirical_full_min 0.683 loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.712(7) 2 0.288(7) ####################################################################### # # 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_179-4 _database_code_depnum_ccdc_archive 'CCDC 2335731' loop_ _audit_author_name _audit_author_address 'zurong Xu' ;South China University of Technology China ; _audit_update_record ; 2024-02-27 deposited with the CCDC. 2024-11-18 downloaded from the CCDC. ; _audit_creation_date 2021-11-27 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _shelx_SHELXL_version_number 2018/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C16 H14 O5' _chemical_formula_sum 'C16 H14 O5' _chemical_formula_weight 286.27 _chemical_absolute_configuration ? _chemical_melting_point ? 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' 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 monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.7856(4) _cell_length_b 6.0442(4) _cell_length_c 16.6292(9) _cell_angle_alpha 90 _cell_angle_beta 92.683(5) _cell_angle_gamma 90 _cell_volume 681.27(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2083 _cell_measurement_temperature 149.99(10) _cell_measurement_theta_max 73.3590 _cell_measurement_theta_min 5.3060 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 0.871 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.77547 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) 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 1.396 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 300 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_unetI/netI 0.0340 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.962 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 2502 _diffrn_reflns_point_group_measured_fraction_full 0.727 _diffrn_reflns_point_group_measured_fraction_max 0.688 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.435 _diffrn_reflns_theta_min 2.660 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 149.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.962 _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 -2.00 61.00 1.00 1.00 -- 40.73 -57.00 0.00 63 2 \w 31.00 134.00 1.00 1.00 -- 106.95 -30.00 -90.00 103 3 \w 93.00 119.00 1.00 1.00 -- 106.95-125.00-180.00 26 4 \w 54.00 80.00 1.00 1.00 -- 106.95-125.00-180.00 26 5 \w 26.00 101.00 1.00 1.00 -- 106.95 -95.00 90.00 75 6 \w 86.00 111.00 1.00 1.00 -- 106.95 45.00 90.00 25 7 \w 132.00 164.00 1.00 1.00 -- 106.95 45.00 90.00 32 8 \w 115.00 177.00 1.00 1.00 -- 106.95 125.00 60.00 62 9 \w 94.00 170.00 1.00 1.00 -- 106.95 125.00 0.00 76 10 \w -34.00 3.00 1.00 1.00 -- 40.73 -77.00 150.00 37 11 \w -67.00 31.00 1.00 1.00 -- -40.73 57.00-120.00 98 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0012453000 _diffrn_orient_matrix_UB_12 0.2295785000 _diffrn_orient_matrix_UB_13 0.0402826000 _diffrn_orient_matrix_UB_21 0.0244265000 _diffrn_orient_matrix_UB_22 -0.1101374000 _diffrn_orient_matrix_UB_23 0.0833625000 _diffrn_orient_matrix_UB_31 0.2260592000 _diffrn_orient_matrix_UB_32 0.0107062000 _diffrn_orient_matrix_UB_33 -0.0048817000 _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 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.302 _reflns_Friedel_fraction_full 0.393 _reflns_Friedel_fraction_max 0.355 _reflns_number_gt 1864 _reflns_number_total 1897 _reflns_odcompleteness_completeness 99.78 _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 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _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 2018/2 (Sheldrick, 2018)' _refine_diff_density_max 0.526 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.107 _refine_ls_abs_structure_details ; Flack x determined using 415 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.1(3) _refine_ls_extinction_coef 0.0157(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 193 _refine_ls_number_reflns 1897 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0834 _refine_ls_restrained_S_all 1.141 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0728P)^2^+3.7566P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2455 _refine_ls_wR_factor_ref 0.2464 _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: C8(H8A,H8B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C12(H12) 2.c Idealised Me refined as rotating group: C14(H14A,H14B,H14C), C16(H16A,H16B,H16C) ; _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 O1 O -0.2023(4) 0.1630(7) 0.0983(2) 0.0340(9) Uani 1 1 d . . . . . O2 O -0.2364(5) 0.5097(8) 0.0509(2) 0.0489(11) Uani 1 1 d . . . . . O3 O 1.3049(4) 0.8989(6) 0.3666(2) 0.0313(9) Uani 1 1 d . . . . . O4 O 1.1353(4) 0.4848(6) 0.39109(17) 0.0239(7) Uani 1 1 d . . . . . O5 O 1.1424(5) 0.6494(7) 0.5123(2) 0.0349(9) Uani 1 1 d . . . . . C1 C 0.0426(6) 0.4200(9) 0.1366(3) 0.0259(11) Uani 1 1 d . . . . . C2 C 0.1268(6) 0.6288(9) 0.1318(3) 0.0271(11) Uani 1 1 d . . . . . H2 H 0.065165 0.737710 0.100148 0.033 Uiso 1 1 calc R U . . . C3 C 0.3034(6) 0.6747(9) 0.1744(2) 0.0234(10) Uani 1 1 d . . . . . H3 H 0.358220 0.815403 0.171695 0.028 Uiso 1 1 calc R U . . . C4 C 0.3990(6) 0.5125(8) 0.2212(2) 0.0224(10) Uani 1 1 d . . . . . C5 C 0.3120(6) 0.3029(8) 0.2268(3) 0.0238(11) Uani 1 1 d . . . . . H5 H 0.373105 0.193487 0.258377 0.029 Uiso 1 1 calc R U . . . C6 C 0.1347(7) 0.2593(9) 0.1849(3) 0.0300(12) Uani 1 1 d . . . . . H6 H 0.076607 0.120689 0.189314 0.036 Uiso 1 1 calc R U . . . C7 C 0.5837(6) 0.5587(8) 0.2657(3) 0.0244(11) Uani 1 1 d . . . . . C8 C 0.7062(6) 0.7681(9) 0.2709(3) 0.0240(11) Uani 1 1 d . . . . . H8A H 0.645955 0.889548 0.298994 0.029 Uiso 1 1 calc R U . . . H8B H 0.758111 0.815634 0.220392 0.029 Uiso 1 1 calc R U . . . C9 C 0.8482(6) 0.6245(9) 0.3238(3) 0.0251(11) Uani 1 1 d . . . . . C10 C 0.7132(6) 0.4399(8) 0.3134(3) 0.0270(12) Uani 1 1 d . . . . . H10 H 0.714517 0.295006 0.332269 0.032 Uiso 1 1 calc R U . . . C11 C 1.0278(6) 0.6586(9) 0.3572(2) 0.0236(10) Uani 1 1 d . . . . . C12 C 1.1272(6) 0.8706(8) 0.3516(3) 0.0250(11) Uani 1 1 d . . . . . H12 H 1.051838 0.992770 0.335619 0.030 Uiso 1 1 calc R U . . . C13 C 1.1993(6) 0.5012(9) 0.4699(3) 0.0268(11) Uani 1 1 d . . . . . C14 C 1.3393(7) 0.3250(10) 0.4927(3) 0.0310(12) Uani 1 1 d . . . . . H14A H 1.274253 0.184241 0.488072 0.046 Uiso 1 1 calc R U . . . H14B H 1.387466 0.346895 0.547354 0.046 Uiso 1 1 calc R U . . . H14C H 1.447808 0.328545 0.457744 0.046 Uiso 1 1 calc R U . . . C15 C -0.1464(6) 0.3769(10) 0.0904(3) 0.0283(12) Uani 1 1 d . . . . . C16 C -0.3860(6) 0.1019(10) 0.0559(3) 0.0360(14) Uani 1 1 d . . . . . H16A H -0.387879 0.159758 0.002148 0.054 Uiso 1 1 calc R U . . . H16B H -0.494799 0.162001 0.083696 0.054 Uiso 1 1 calc R U . . . H16C H -0.396928 -0.056341 0.053978 0.054 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0229(14) 0.0363(19) 0.0415(17) 0.0049(17) -0.0115(13) -0.0096(15) O2 0.044(2) 0.037(2) 0.063(2) 0.010(2) -0.0236(17) -0.0041(19) O3 0.0229(14) 0.0336(18) 0.0371(16) 0.0009(16) -0.0010(12) -0.0088(15) O4 0.0233(13) 0.0251(15) 0.0231(12) -0.0021(14) -0.0009(11) 0.0040(14) O5 0.0354(16) 0.0372(19) 0.0316(15) -0.0107(17) -0.0025(13) 0.0087(17) C1 0.0202(18) 0.029(3) 0.028(2) -0.001(2) -0.0041(16) -0.0001(19) C2 0.026(2) 0.028(2) 0.027(2) 0.005(2) -0.0071(16) 0.003(2) C3 0.0181(17) 0.024(2) 0.0281(19) 0.001(2) 0.0069(15) -0.0058(18) C4 0.0159(17) 0.028(2) 0.0235(17) -0.003(2) 0.0040(14) 0.0025(19) C5 0.0169(18) 0.027(2) 0.0276(19) 0.005(2) -0.0021(16) 0.0007(19) C6 0.032(2) 0.022(2) 0.034(2) 0.005(2) -0.0069(19) -0.003(2) C7 0.024(2) 0.025(2) 0.0246(19) 0.0005(19) -0.0016(17) -0.0011(19) C8 0.0167(18) 0.028(2) 0.0273(19) 0.003(2) 0.0056(16) 0.0021(19) C9 0.0243(19) 0.023(2) 0.0278(19) 0.002(2) 0.0016(16) -0.003(2) C10 0.024(2) 0.026(3) 0.032(2) 0.000(2) 0.0046(17) -0.0018(19) C11 0.0236(19) 0.024(2) 0.0225(18) 0.000(2) -0.0033(16) -0.004(2) C12 0.0238(19) 0.021(2) 0.030(2) -0.002(2) -0.0007(16) -0.002(2) C13 0.0196(18) 0.031(2) 0.030(2) -0.001(2) -0.0011(16) -0.009(2) C14 0.026(2) 0.038(3) 0.029(2) 0.005(2) -0.0014(17) 0.002(2) C15 0.0185(18) 0.035(3) 0.030(2) 0.000(2) -0.0052(16) 0.000(2) C16 0.021(2) 0.048(3) 0.039(2) 0.006(3) -0.0091(18) -0.013(2) _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 O1 C15 1.355(7) . ? O1 C16 1.451(5) . ? O2 C15 1.188(7) . ? O3 C12 1.232(5) . ? O4 C11 1.384(6) . ? O4 C13 1.365(5) . ? O5 C13 1.215(6) . ? C1 C2 1.389(7) . ? C1 C6 1.391(7) . ? C1 C15 1.486(6) . ? C2 H2 0.9300 . ? C2 C3 1.392(6) . ? C3 H3 0.9300 . ? C3 C4 1.393(6) . ? C4 C5 1.402(7) . ? C4 C7 1.452(6) . ? C5 H5 0.9300 . ? C5 C6 1.386(6) . ? C6 H6 0.9300 . ? C7 C8 1.515(7) . ? C7 C10 1.361(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.541(6) . ? C9 C10 1.449(7) . ? C9 C11 1.332(6) . ? C10 H10 0.9300 . ? C11 C12 1.453(7) . ? C12 H12 0.9300 . ? C13 C14 1.465(7) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O1 C16 115.7(4) . . ? C13 O4 C11 118.3(4) . . ? C2 C1 C6 119.5(4) . . ? C2 C1 C15 118.5(4) . . ? C6 C1 C15 122.0(5) . . ? C1 C2 H2 120.0 . . ? C1 C2 C3 119.9(4) . . ? C3 C2 H2 120.0 . . ? C2 C3 H3 119.6 . . ? C2 C3 C4 120.8(5) . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 119.1(4) . . ? C3 C4 C7 121.1(4) . . ? C5 C4 C7 119.7(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 C4 119.8(4) . . ? C6 C5 H5 120.1 . . ? C1 C6 H6 119.6 . . ? C5 C6 C1 120.9(5) . . ? C5 C6 H6 119.6 . . ? C4 C7 C8 130.4(4) . . ? C10 C7 C4 135.5(5) . . ? C10 C7 C8 94.0(4) . . ? C7 C8 H8A 114.7 . . ? C7 C8 H8B 114.7 . . ? C7 C8 C9 83.6(4) . . ? H8A C8 H8B 111.8 . . ? C9 C8 H8A 114.7 . . ? C9 C8 H8B 114.7 . . ? C10 C9 C8 89.5(3) . . ? C11 C9 C8 133.4(5) . . ? C11 C9 C10 136.9(5) . . ? C7 C10 C9 92.9(4) . . ? C7 C10 H10 133.6 . . ? C9 C10 H10 133.6 . . ? O4 C11 C12 117.2(4) . . ? C9 C11 O4 120.5(5) . . ? C9 C11 C12 121.9(4) . . ? O3 C12 C11 124.2(4) . . ? O3 C12 H12 117.9 . . ? C11 C12 H12 117.9 . . ? O4 C13 C14 111.7(4) . . ? O5 C13 O4 121.1(4) . . ? O5 C13 C14 127.2(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 C15 C1 110.8(4) . . ? O2 C15 O1 124.0(4) . . ? O2 C15 C1 125.1(5) . . ? O1 C16 H16A 109.5 . . ? O1 C16 H16B 109.5 . . ? O1 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 C11 C12 O3 8.3(7) . . . . ? C1 C2 C3 C4 0.9(7) . . . . ? C2 C1 C6 C5 -1.7(7) . . . . ? C2 C1 C15 O1 176.7(4) . . . . ? C2 C1 C15 O2 -2.4(7) . . . . ? C2 C3 C4 C5 -1.8(6) . . . . ? C2 C3 C4 C7 179.8(4) . . . . ? C3 C4 C5 C6 1.0(6) . . . . ? C3 C4 C7 C8 -1.0(7) . . . . ? C3 C4 C7 C10 -177.8(5) . . . . ? C4 C5 C6 C1 0.8(7) . . . . ? C4 C7 C8 C9 -177.2(5) . . . . ? C4 C7 C10 C9 176.9(5) . . . . ? C5 C4 C7 C8 -179.3(4) . . . . ? C5 C4 C7 C10 3.8(8) . . . . ? C6 C1 C2 C3 0.8(7) . . . . ? C6 C1 C15 O1 -4.3(6) . . . . ? C6 C1 C15 O2 176.6(5) . . . . ? C7 C4 C5 C6 179.4(4) . . . . ? C7 C8 C9 C10 -0.6(3) . . . . ? C7 C8 C9 C11 173.9(5) . . . . ? C8 C7 C10 C9 -0.6(4) . . . . ? C8 C9 C10 C7 0.6(4) . . . . ? C8 C9 C11 O4 -169.0(4) . . . . ? C8 C9 C11 C12 3.8(8) . . . . ? C9 C11 C12 O3 -164.7(5) . . . . ? C10 C7 C8 C9 0.6(4) . . . . ? C10 C9 C11 O4 2.9(8) . . . . ? C10 C9 C11 C12 175.7(5) . . . . ? C11 O4 C13 O5 9.6(6) . . . . ? C11 O4 C13 C14 -169.8(4) . . . . ? C11 C9 C10 C7 -173.5(6) . . . . ? C13 O4 C11 C9 -123.2(5) . . . . ? C13 O4 C11 C12 63.7(5) . . . . ? C15 C1 C2 C3 179.8(4) . . . . ? C15 C1 C6 C5 179.3(4) . . . . ? C16 O1 C15 O2 -1.2(7) . . . . ? C16 O1 C15 C1 179.7(4) . . . . ? _shelx_res_file ; TITL 179-4_a.res in P2(1) 179-4.res created by SHELXL-2018/3 at 17:01:18 on 27-Nov-2021 REM Old TITL 179-4 in P2(1)/m REM SHELXT solution in P2(1): R1 0.123, Rweak 0.059, Alpha 0.002 REM 1.375 for 4 systematic absences, Orientation as input REM Flack x = 0.495 ( 0.296 ) from 433 Parsons' quotients REM Formula found by SHELXT: C16 O5 CELL 1.54184 6.7856 6.0442 16.6292 90 92.683 90 ZERR 2 0.0004 0.0004 0.0009 0 0.005 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H O UNIT 32 28 10 L.S. 10 PLAN 5 CONF FREE C9 C7 BOND list 4 fmap 2 53 MORE -1 ACTA BOND $H REM REM REM WGHT 0.072800 3.756600 EXTI 0.015747 FVAR 1.31074 O1 3 -0.202264 0.162998 0.098288 11.00000 0.02292 0.03630 = 0.04148 0.00494 -0.01150 -0.00961 O2 3 -0.236380 0.509711 0.050930 11.00000 0.04398 0.03698 = 0.06343 0.01032 -0.02360 -0.00408 O3 3 1.304919 0.898851 0.366631 11.00000 0.02294 0.03362 = 0.03711 0.00089 -0.00097 -0.00884 O4 3 1.135325 0.484806 0.391086 11.00000 0.02330 0.02514 = 0.02306 -0.00213 -0.00090 0.00395 O5 3 1.142405 0.649408 0.512344 11.00000 0.03538 0.03725 = 0.03161 -0.01072 -0.00253 0.00866 C1 1 0.042573 0.419962 0.136571 11.00000 0.02016 0.02914 = 0.02778 -0.00055 -0.00411 -0.00006 C2 1 0.126764 0.628753 0.131802 11.00000 0.02600 0.02758 = 0.02692 0.00532 -0.00714 0.00339 AFIX 43 H2 2 0.065165 0.737710 0.100148 11.00000 -1.20000 AFIX 0 C3 1 0.303413 0.674733 0.174446 11.00000 0.01813 0.02449 = 0.02812 0.00089 0.00689 -0.00581 AFIX 43 H3 2 0.358220 0.815403 0.171695 11.00000 -1.20000 AFIX 0 C4 1 0.399046 0.512452 0.221199 11.00000 0.01591 0.02798 = 0.02350 -0.00332 0.00397 0.00253 C5 1 0.312045 0.302868 0.226753 11.00000 0.01687 0.02659 = 0.02757 0.00532 -0.00206 0.00073 AFIX 43 H5 2 0.373105 0.193487 0.258377 11.00000 -1.20000 AFIX 0 C6 1 0.134720 0.259256 0.184949 11.00000 0.03224 0.02246 = 0.03442 0.00497 -0.00687 -0.00312 AFIX 43 H6 2 0.076607 0.120689 0.189314 11.00000 -1.20000 AFIX 0 C7 1 0.583734 0.558665 0.265678 11.00000 0.02371 0.02460 = 0.02465 0.00052 -0.00163 -0.00105 C8 1 0.706159 0.768140 0.270937 11.00000 0.01671 0.02838 = 0.02733 0.00275 0.00556 0.00210 AFIX 23 H8A 2 0.645955 0.889548 0.298994 11.00000 -1.20000 H8B 2 0.758111 0.815634 0.220392 11.00000 -1.20000 AFIX 0 C9 1 0.848152 0.624528 0.323785 11.00000 0.02425 0.02346 = 0.02776 0.00160 0.00158 -0.00309 C10 1 0.713189 0.439890 0.313423 11.00000 0.02357 0.02627 = 0.03157 0.00033 0.00459 -0.00176 AFIX 43 H10 2 0.714517 0.295006 0.332269 11.00000 -1.20000 AFIX 0 C11 1 1.027767 0.658561 0.357206 11.00000 0.02361 0.02437 = 0.02247 -0.00041 -0.00333 -0.00391 C12 1 1.127211 0.870575 0.351593 11.00000 0.02378 0.02125 = 0.02966 -0.00156 -0.00067 -0.00172 AFIX 43 H12 2 1.051838 0.992770 0.335619 11.00000 -1.20000 AFIX 0 C13 1 1.199266 0.501196 0.469891 11.00000 0.01962 0.03105 = 0.02962 -0.00135 -0.00109 -0.00866 C14 1 1.339265 0.325035 0.492734 11.00000 0.02551 0.03789 = 0.02935 0.00462 -0.00136 0.00231 AFIX 137 H14A 2 1.274253 0.184241 0.488072 11.00000 -1.50000 H14B 2 1.387466 0.346895 0.547354 11.00000 -1.50000 H14C 2 1.447808 0.328545 0.457744 11.00000 -1.50000 AFIX 0 C15 1 -0.146401 0.376854 0.090416 11.00000 0.01847 0.03543 = 0.03040 -0.00016 -0.00520 0.00038 C16 1 -0.386002 0.101942 0.055948 11.00000 0.02062 0.04761 = 0.03874 0.00582 -0.00914 -0.01262 AFIX 137 H16A 2 -0.387879 0.159758 0.002148 11.00000 -1.50000 H16B 2 -0.494799 0.162001 0.083696 11.00000 -1.50000 H16C 2 -0.396928 -0.056341 0.053978 11.00000 -1.50000 AFIX 0 HKLF 4 REM 179-4_a.res in P2(1) REM wR2 = 0.2464, GooF = S = 1.141, Restrained GooF = 1.141 for all data REM R1 = 0.0834 for 1864 Fo > 4sig(Fo) and 0.0853 for all 1897 data REM 193 parameters refined using 1 restraints END WGHT 0.0725 3.7592 REM Highest difference peak 0.526, deepest hole -0.362, 1-sigma level 0.107 Q1 1 0.9118 0.4811 0.3925 11.00000 0.05 0.53 Q2 1 1.3720 0.6676 0.5174 11.00000 0.05 0.49 Q3 1 1.4388 0.5218 0.4667 11.00000 0.05 0.42 Q4 1 1.4119 0.1671 0.4798 11.00000 0.05 0.42 Q5 1 1.5891 0.3328 0.4966 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7 -1 51.53 3.06 1 7 0 7.38 1.14 1 7 1 19.13 1.82 1 7 2 25.68 2.00 1 7 3 19.29 1.64 1 7 4 3.92 0.70 1 7 5 5.91 0.79 2 0 -20 24.71 2.01 2 0 -19 128.25 6.17 2 0 -18 45.42 4.40 2 0 -17 3.19 1.25 2 0 -16 178.10 9.99 2 0 -15 19.36 3.34 2 0 -14 24.52 3.76 2 0 -13 294.69 12.71 2 0 -13 328.81 13.24 2 0 -12 8.78 2.09 2 0 -12 10.76 2.23 2 0 -11 50.03 4.73 2 0 -11 45.24 4.60 2 0 -10 359.58 11.91 2 0 -9 348.66 10.83 2 0 -8 1932.85 23.62 2 0 -7 216.59 7.36 2 0 -6 16.69 1.87 2 0 -5 6.98 1.09 2 0 -4 62.12 3.02 2 0 -3 64.46 2.93 2 0 -2 549.88 8.13 2 0 -1 390.04 4.92 2 0 -1 353.22 6.44 2 0 0 4728.29 18.92 2 0 0 4720.37 21.71 2 0 1 148.20 3.57 2 0 1 133.90 3.37 2 0 2 40.31 2.01 2 0 3 163.02 4.32 2 0 4 234.57 5.55 2 0 5 901.61 11.68 2 0 6 0.31 0.26 2 0 7 506.46 10.13 2 0 8 736.90 13.03 2 0 9 2.77 0.86 2 0 10 17.85 2.31 2 0 11 9.92 1.80 2 0 11 20.60 2.64 2 0 12 44.32 4.03 2 0 12 44.60 4.08 2 0 13 138.91 7.50 -2 0 -13 129.84 6.52 2 0 13 116.59 6.94 2 0 14 836.50 18.95 2 0 15 397.55 13.19 -2 0 -16 153.41 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2 -2 -16 4.57 1.44 2 -2 -15 36.11 4.59 2 -2 -14 73.65 6.65 2 -2 -13 163.86 9.87 2 -2 -12 22.96 3.52 2 -2 -12 24.07 3.87 2 2 -12 19.98 2.80 2 -2 -11 70.75 6.38 2 -2 -11 76.42 6.31 2 2 -11 76.00 5.14 2 2 -10 77.58 4.75 2 -2 -10 79.37 6.13 2 -2 -10 70.59 6.10 2 -2 -9 73.93 5.86 2 2 -9 82.98 4.50 2 2 -8 346.33 8.40 2 -2 -8 343.39 12.03 2 2 -7 885.82 12.51 2 -2 -7 886.14 18.32 2 2 -6 293.82 6.55 2 -2 -6 295.43 10.09 2 -2 -5 408.88 11.29 2 2 -5 401.03 6.86 2 2 -4 99.19 3.01 2 -2 -4 101.16 5.44 2 -2 -3 1008.43 16.41 2 -2 -2 1390.50 18.43 2 -2 -1 719.62 13.21 2 -2 0 98.23 4.47 2 -2 1 313.07 8.00 2 -2 1 271.07 7.35 2 -2 2 1041.01 14.96 2 -2 3 1835.38 20.16 2 2 4 49.47 2.79 2 -2 4 69.17 3.99 2 2 5 39.84 2.56 2 -2 5 37.61 3.10 2 2 6 69.94 3.56 2 -2 6 64.96 4.20 2 2 7 223.83 6.70 2 -2 7 210.63 7.81 2 -2 8 38.95 3.45 2 2 8 41.94 3.03 2 2 9 58.45 3.80 2 2 9 54.43 3.69 2 -2 9 53.90 4.19 -2 2 -9 55.89 4.24 -2 2 -10 155.37 7.42 2 2 10 156.23 6.49 2 2 11 39.23 3.45 2 2 11 44.98 3.70 -2 2 -11 40.76 3.99 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2 3 7 7.17 1.32 2 3 7 9.25 1.58 -2 3 -7 7.20 1.61 2 -3 7 6.78 1.60 2 3 8 43.26 3.47 -2 3 -8 35.58 3.73 2 3 8 37.23 3.18 2 -3 8 36.52 3.93 2 3 9 197.43 7.59 -2 3 -9 185.98 8.88 2 -3 9 178.90 8.78 2 3 10 57.18 4.13 2 3 10 52.81 4.11 -2 3 -10 53.77 4.95 -2 3 -11 128.70 7.87 2 3 11 122.34 6.11 -2 3 -12 87.75 6.57 2 3 12 93.11 5.50 2 3 13 41.94 3.73 2 3 14 35.15 3.39 2 3 15 15.13 2.13 2 3 16 2.48 0.82 2 3 17 3.04 0.81 2 3 18 92.62 3.74 2 4 -16 20.28 2.11 2 4 -15 126.80 5.93 2 4 -15 125.54 5.85 2 4 -14 154.40 7.12 2 4 -14 150.43 7.39 2 4 -13 391.00 13.18 2 4 -12 200.20 9.98 2 4 -11 91.66 7.04 2 4 -10 87.98 7.03 2 4 -9 6.12 1.89 2 4 -8 6.38 1.90 2 4 -7 14.67 2.88 2 -4 -7 19.81 3.28 2 -4 -6 12.74 2.45 2 4 -6 15.40 2.92 2 -4 -5 0.12 0.34 2 4 -5 0.71 0.48 2 4 -4 91.95 6.90 2 -4 -4 83.78 5.67 2 4 -3 54.37 5.18 2 -4 -3 44.91 4.20 2 -4 -2 136.75 7.02 -2 -4 2 146.56 7.28 2 4 -1 35.20 4.04 2 4 0 50.52 4.64 2 4 1 89.92 6.22 2 -4 2 54.60 4.99 2 4 2 63.47 5.15 2 4 3 92.52 6.03 2 -4 3 87.03 6.54 2 4 4 82.12 5.42 2 -4 4 72.03 5.98 2 -4 5 46.01 4.83 2 4 5 52.41 4.20 2 4 6 36.24 3.41 2 4 6 38.95 3.59 2 -4 6 34.01 4.21 2 4 7 11.33 1.89 2 4 7 13.84 2.10 2 -4 7 12.62 2.58 2 4 8 75.35 4.87 2 4 9 222.31 8.24 2 4 10 788.74 15.41 2 4 11 148.06 6.55 2 4 12 58.61 4.12 2 4 13 241.45 8.22 2 4 14 26.90 2.61 2 4 15 6.89 1.24 -2 4 -16 13.39 1.83 2 4 16 12.43 1.45 2 5 -14 92.47 4.55 2 5 -14 93.60 4.38 2 5 -13 10.26 1.65 2 5 -13 9.94 1.67 2 5 -12 15.41 2.20 2 5 -12 15.79 2.38 2 5 -11 32.67 3.64 2 5 -11 33.15 3.41 2 5 -10 77.71 5.99 2 5 -9 40.73 4.52 2 5 -8 112.00 7.67 2 5 -7 11.31 2.50 2 5 -6 43.80 4.90 2 5 -5 18.91 3.23 2 5 -4 218.69 9.34 2 5 -4 226.23 11.25 2 5 -3 452.45 16.05 2 5 -2 89.01 6.66 2 5 -1 13.79 2.64 2 5 0 276.00 11.62 2 5 1 51.80 4.95 2 5 2 141.86 8.02 2 5 3 17.84 2.67 2 5 4 26.45 3.10 2 5 5 15.86 2.32 2 5 6 69.80 4.75 -2 5 -6 64.84 5.56 2 5 7 303.30 9.63 -2 5 -7 302.14 12.00 2 5 8 68.08 4.40 -2 5 -8 66.79 5.65 2 5 9 144.28 6.15 -2 5 -9 141.47 8.07 2 5 10 39.22 3.10 -2 5 -10 41.80 4.25 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9.37 2.58 3 0 -11 7.54 1.98 3 0 -10 1.42 0.97 3 0 -10 2.53 1.08 3 0 -9 79.85 5.83 3 0 -8 30.67 3.38 3 0 -7 15.80 2.28 3 0 -6 108.86 5.56 3 0 -5 4.31 1.02 3 0 -4 423.32 9.78 3 0 -3 443.55 9.46 3 0 -2 386.92 8.37 3 0 -1 768.79 9.32 3 0 -1 728.93 10.98 3 0 0 22.71 1.75 3 0 0 15.49 1.39 3 0 1 879.53 11.38 3 0 2 1731.81 16.88 3 0 3 3.94 0.89 3 0 4 48.93 3.12 3 0 5 969.86 14.68 3 0 6 2.06 0.76 3 0 7 64.28 4.20 3 0 8 6.62 1.42 3 0 9 2.75 0.95 3 0 10 984.55 19.39 3 0 10 934.47 17.01 3 0 11 41.01 3.72 3 0 11 57.78 4.77 3 0 12 26.53 3.13 3 0 13 37.55 3.80 3 0 14 280.40 10.44 3 0 15 67.38 4.84 -3 0 -16 10.71 1.86 3 0 17 42.73 4.09 -3 0 -17 50.04 3.67 3 0 18 0.32 0.37 -3 0 -18 1.16 0.53 3 -1 -19 4.86 0.98 3 1 -18 6.10 1.11 3 -1 -18 6.96 1.47 3 -1 -17 6.98 1.71 3 1 -17 6.31 1.37 3 -1 -16 184.41 9.96 3 1 -16 137.08 7.23 3 -1 -15 92.48 7.50 3 1 -15 70.12 5.78 3 1 -14 62.13 5.68 3 -1 -14 78.23 7.13 3 1 -13 113.51 7.91 3 -1 -13 121.57 8.99 3 -1 -12 604.23 19.90 3 1 -12 623.36 17.98 3 -1 -12 632.60 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67.53 6.22 5 1 -7 66.84 3.94 5 -1 -7 58.11 3.67 5 -1 -7 90.48 7.17 5 1 -7 97.75 7.02 5 -1 -7 103.58 7.19 5 -1 -6 50.07 4.87 5 1 -6 47.06 4.81 5 1 -6 6.34 2.34 5 1 -6 10.58 1.86 5 -1 -6 38.07 3.40 5 -1 -6 42.05 4.73 5 -1 -5 70.81 5.01 5 1 -5 79.32 6.56 5 1 -5 147.39 8.15 5 1 -5 75.84 4.19 5 -1 -5 136.93 6.41 5 -1 -5 120.00 7.53 5 -1 -5 141.45 7.98 5 -1 -4 100.08 5.86 5 1 -4 110.21 7.34 5 1 -4 100.78 4.65 5 -1 -4 104.73 6.03 5 -1 -4 93.77 6.00 5 1 -4 89.12 6.22 5 -1 -4 86.04 6.01 5 -1 -3 361.19 10.75 5 -1 -3 304.44 10.43 5 -1 -3 431.35 12.94 5 1 -3 332.72 12.43 5 1 -3 325.16 8.33 5 -1 -3 453.17 12.99 5 -1 -3 377.98 11.25 5 1 -3 470.40 14.29 5 -1 -2 12.88 2.28 5 -1 -2 14.30 2.23 5 1 -2 7.60 2.51 5 1 -2 12.97 1.65 5 -1 -2 80.55 5.66 5 -1 -2 59.71 4.42 5 1 -2 92.03 6.14 5 -1 -2 92.83 5.96 5 -1 -1 8.58 1.93 5 1 -1 10.28 2.41 5 1 -1 9.53 1.49 5 -1 -1 58.66 5.19 5 1 -1 65.77 5.29 5 -1 -1 48.18 4.55 5 -1 0 134.76 6.40 5 1 0 148.65 7.66 5 1 0 120.25 4.97 5 -1 0 110.09 6.98 5 -1 1 190.06 7.57 5 1 1 178.90 6.09 5 1 2 641.41 14.98 5 -1 2 594.85 13.42 5 1 2 561.28 10.62 5 -1 2 660.68 18.33 5 1 2 573.20 15.61 5 1 3 57.30 4.38 5 -1 3 51.42 3.99 5 1 3 50.99 3.16 5 1 3 46.06 4.13 5 -1 3 89.88 6.89 5 1 3 76.32 5.95 5 -1 4 226.52 8.31 5 1 4 207.37 8.85 5 -1 4 237.21 11.39 5 1 4 202.49 9.43 5 -1 5 106.58 5.67 5 1 5 92.98 6.14 5 -1 5 96.09 7.24 5 1 5 90.92 6.41 5 -1 6 153.29 6.76 5 -1 6 142.69 9.05 5 1 6 136.92 8.26 5 -1 7 28.89 4.36 5 1 7 27.45 4.00 5 -1 8 135.88 9.06 5 1 8 138.21 8.75 5 1 9 690.78 19.65 5 -1 9 705.41 20.73 5 1 10 153.91 9.30 -5 1 -10 181.82 7.39 5 -1 10 160.19 9.73 5 1 11 63.00 5.85 -5 1 -11 67.88 4.43 5 -1 11 73.07 6.32 -5 1 -12 98.17 5.13 5 -1 12 92.41 6.66 5 1 12 92.50 6.70 -5 1 -13 23.99 2.42 5 -1 13 25.90 3.27 5 1 13 21.38 3.03 -5 1 -14 7.31 1.23 5 -1 14 8.89 1.76 5 1 14 7.86 1.67 -5 1 -15 32.14 2.30 -5 -1 -15 35.81 2.44 5 -1 15 31.10 2.77 5 1 15 27.64 2.50 5 -2 -15 25.36 2.46 5 -2 -14 8.25 1.69 5 2 -13 17.16 2.39 5 2 -13 19.05 2.24 5 -2 -13 19.78 2.74 5 2 -12 28.36 3.53 5 2 -12 23.33 2.66 5 -2 -12 25.16 3.26 5 2 -11 35.24 4.35 5 2 -11 35.60 3.60 5 -2 -11 45.49 4.52 5 2 -10 20.29 2.76 5 -2 -10 19.17 2.92 5 2 -9 77.95 5.52 5 -2 -9 90.04 6.43 5 2 -8 251.38 10.41 5 -2 -8 296.72 11.45 5 2 -7 107.52 6.71 5 -2 -7 118.14 7.13 5 2 -6 66.21 6.75 5 2 -6 56.09 4.88 5 -2 -6 55.02 4.76 5 -2 -5 89.95 5.56 5 2 -5 83.93 7.76 5 2 -5 114.15 5.46 5 -2 -5 279.68 9.55 5 -2 -5 247.91 11.08 5 2 -5 326.56 11.84 5 -2 -5 341.80 11.58 5 -2 -4 219.74 8.50 5 2 -4 255.82 12.59 5 2 -4 256.69 7.99 5 -2 -4 303.69 10.02 5 -2 -4 266.99 10.44 5 2 -4 316.94 11.40 5 -2 -4 298.04 10.35 5 -2 -3 673.60 14.71 5 2 -3 713.20 19.84 5 2 -3 703.93 12.62 5 -2 -3 736.60 16.66 5 -2 -3 687.77 17.33 5 2 -3 700.63 17.15 5 -2 -3 676.70 15.59 5 -2 -2 595.08 13.71 5 2 -2 644.13 18.06 5 2 -2 618.44 11.55 5 -2 -2 531.56 14.63 5 -2 -2 502.71 14.30 5 -2 -1 53.69 4.63 5 2 -1 48.70 3.38 5 2 0 685.44 16.91 5 -2 0 686.96 15.12 5 2 0 710.23 12.23 5 2 1 90.07 6.28 5 2 1 94.26 4.40 5 2 2 603.02 15.44 5 -2 2 612.69 15.57 5 2 2 583.43 10.66 5 2 3 471.24 12.80 5 -2 3 460.77 13.50 5 -2 3 444.60 15.36 5 2 4 811.06 15.81 5 -2 4 757.79 17.46 5 -2 5 47.04 4.37 5 -2 5 58.00 5.88 5 -2 6 280.09 10.32 5 -2 6 216.83 11.24 5 -2 7 677.92 15.04 5 -2 7 529.85 17.65 5 -2 8 179.07 7.29 5 -2 8 136.72 8.83 5 -2 9 11.09 2.53 5 -2 10 52.83 5.13 5 -2 11 24.21 3.26 5 -2 12 31.54 3.46 5 -2 13 25.93 2.82 5 -2 14 24.65 2.38 5 3 -14 14.23 1.62 5 3 -13 40.77 3.47 5 3 -12 32.04 3.56 5 3 -11 93.46 6.82 5 3 -10 34.28 4.47 5 3 -9 41.31 5.04 5 3 -8 195.19 11.22 5 3 -7 12.58 3.26 5 3 -6 219.93 12.40 5 -3 -5 331.37 10.04 5 3 -5 332.67 15.28 5 -3 -4 474.71 12.27 5 3 -4 498.01 18.25 5 -3 -4 485.28 12.38 5 -3 -3 789.57 15.95 5 -3 -3 769.14 15.56 5 -3 -2 211.93 8.45 5 3 -2 227.48 11.26 5 -3 -2 196.21 8.30 5 3 -1 239.86 10.99 5 -3 -1 245.50 9.77 5 -3 0 332.53 11.85 5 -3 0 326.65 11.55 5 3 1 105.77 6.58 5 -3 1 124.05 7.52 5 -3 2 781.46 19.83 5 -3 2 820.33 19.95 5 -3 3 507.96 16.05 5 -3 3 519.10 15.93 5 -3 4 104.22 7.33 5 -3 4 172.55 9.07 5 -3 5 178.37 9.41 5 -3 5 175.87 9.29 5 -3 6 147.95 8.16 5 -3 6 97.35 6.72 5 -3 7 53.43 4.76 5 -3 7 86.55 6.40 5 -3 8 9.85 1.83 5 -3 8 12.02 2.33 5 -3 9 10.49 1.61 5 -3 9 12.10 2.21 5 -3 10 54.35 4.28 5 -3 11 14.25 1.97 5 -3 12 9.35 1.39 5 4 -12 0.53 0.25 5 4 -11 28.62 3.09 5 4 -10 1.23 0.69 5 4 -9 252.22 10.94 5 4 -8 20.66 3.26 5 4 -7 62.40 6.08 5 4 -6 38.34 4.71 5 4 -5 13.90 2.83 5 -4 -4 8.70 1.57 5 4 -4 7.28 1.95 5 -4 -3 129.88 6.15 5 4 -3 125.95 7.97 5 -4 -2 21.33 2.60 5 4 -2 19.03 2.98 5 4 -1 262.24 10.18 5 -4 -1 267.19 9.92 5 4 0 35.12 3.63 5 -4 0 47.84 4.72 5 -4 1 24.97 3.29 5 -4 1 23.45 2.51 5 -4 2 16.57 3.17 5 -4 2 55.75 4.00 5 -4 3 8.94 2.02 5 -4 3 7.29 1.45 5 4 4 17.13 1.95 5 -4 4 24.92 3.41 5 -4 4 20.24 2.40 5 4 5 36.67 2.79 5 -4 5 48.20 4.66 5 4 6 117.02 4.88 5 -4 6 145.94 7.53 5 4 7 11.73 1.50 5 -4 7 13.73 2.15 5 -4 8 78.16 4.60 5 4 8 80.87 3.92 5 4 9 0.81 0.35 5 -4 9 1.79 0.60 5 -4 10 88.71 3.42 5 4 10 79.01 3.40 5 5 -9 7.41 1.25 5 5 -8 2.75 0.93 5 5 -7 7.45 1.42 5 5 -6 10.37 1.77 5 5 -5 65.81 4.33 5 5 -4 7.34 1.41 5 -5 -3 39.16 2.82 5 5 -3 27.19 2.62 5 -5 -2 24.43 2.35 5 -5 -1 88.05 4.61 5 -5 0 103.21 5.18 5 5 0 96.62 4.34 5 -5 1 60.40 4.11 5 5 1 53.26 3.16 5 5 2 29.13 2.29 5 -5 2 36.67 3.32 5 5 3 11.35 1.37 5 -5 3 12.38 1.92 5 5 4 41.36 2.56 5 -5 4 49.47 3.75 5 5 5 53.28 2.79 5 -5 5 66.20 4.12 5 5 6 35.62 2.17 5 -5 6 45.03 3.14 5 -5 7 79.08 3.63 5 5 7 67.73 2.85 5 -5 8 1.80 0.49 6 0 -15 7.61 1.12 6 0 -14 9.38 1.47 6 0 -13 8.19 1.53 6 0 -12 0.75 0.51 6 0 -11 7.76 1.80 6 0 -10 57.50 5.06 6 0 -9 4.98 1.56 6 0 -9 8.00 1.30 6 0 -9 5.65 1.30 6 0 -8 5.77 2.00 6 0 -8 3.70 1.13 6 0 -8 3.62 0.88 6 0 -7 7.02 1.68 6 0 -7 7.19 1.26 6 0 -6 63.77 5.16 6 0 -6 61.00 3.71 6 0 -5 14.11 2.43 6 0 -5 11.39 1.57 6 0 -5 10.55 1.96 6 0 -4 8.32 2.10 6 0 -4 9.12 1.97 6 0 -4 9.42 1.44 6 0 -4 6.49 1.39 6 0 -3 305.84 11.15 6 0 -3 285.85 8.34 6 0 -3 235.04 8.70 6 0 -3 247.45 11.13 6 0 -2 1.87 1.64 6 0 -2 1.66 0.86 6 0 -1 305.49 10.72 6 0 -1 251.71 9.79 6 0 0 147.59 8.15 6 0 1 43.37 4.38 6 0 2 103.98 6.89 6 0 3 44.66 4.67 6 0 4 75.25 6.15 6 0 5 107.72 7.60 6 0 6 813.17 21.15 6 0 7 187.01 9.95 6 0 8 102.92 7.22 6 0 9 0.04 0.21 6 0 10 26.26 3.39 6 0 11 2.61 0.96 6 0 12 136.92 6.71 6 0 13 0.59 0.41 6 1 -14 11.89 1.48 6 -1 -14 11.96 1.62 6 1 -13 3.70 0.96 6 -1 -13 3.58 0.96 6 1 -12 3.75 1.12 6 -1 -12 4.42 1.26 6 1 -11 28.28 3.26 6 -1 -11 30.96 3.43 6 1 -10 17.04 2.70 6 -1 -10 18.46 2.78 6 1 -9 158.14 8.11 6 -1 -9 167.40 5.19 6 1 -9 96.82 6.61 6 -1 -9 97.63 6.62 6 1 -8 47.44 4.61 6 -1 -8 51.58 3.12 6 1 -8 31.92 3.87 6 -1 -8 31.60 3.81 6 1 -7 138.68 8.08 6 1 -7 159.31 6.06 6 -1 -7 135.76 5.23 6 1 -7 96.42 6.91 6 -1 -7 99.38 6.74 6 1 -6 170.91 9.11 6 1 -6 182.93 6.47 6 -1 -6 154.13 5.76 6 1 -6 128.63 7.97 6 -1 -6 136.99 8.11 6 1 -5 139.87 8.29 6 1 -5 145.75 5.88 6 -1 -5 118.30 6.00 6 1 -5 104.88 7.18 6 -1 -5 101.45 6.95 6 1 -4 12.19 2.48 6 1 -4 11.78 1.66 6 -1 -4 9.59 2.07 6 -1 -4 9.73 2.28 6 -1 -3 6.77 1.86 6 1 -3 7.43 1.90 6 1 -3 8.38 1.37 6 -1 -3 12.00 2.44 6 1 -2 0.92 0.82 6 1 -2 0.47 0.31 6 1 -1 32.24 3.71 6 1 -1 26.23 2.41 6 -1 -1 30.81 3.60 6 1 0 159.09 5.94 6 -1 0 151.62 8.29 6 1 1 33.17 3.58 6 1 1 29.93 2.53 6 -1 1 27.55 3.69 6 1 2 146.41 5.49 6 1 2 139.95 7.36 6 -1 2 131.80 8.08 6 1 3 124.92 4.90 6 1 3 115.30 6.72 6 -1 3 115.02 7.72 6 1 4 115.04 6.85 6 -1 4 135.89 8.70 6 1 5 226.56 9.94 6 -1 5 240.54 11.59 6 -1 6 63.76 6.06 6 1 6 65.13 5.41 6 -1 7 40.12 4.71 6 1 7 36.50 4.06 6 -1 8 26.20 3.71 6 1 8 21.94 3.11 6 -1 9 39.72 4.33 6 1 9 37.13 3.86 6 -1 10 30.80 3.69 6 1 10 27.13 3.15 6 -1 11 22.86 2.92 6 1 11 21.55 2.61 6 -1 12 8.95 1.63 6 1 12 7.52 1.37 6 -1 13 76.16 4.08 6 -2 -13 19.88 2.00 6 2 -12 43.65 3.20 6 -2 -12 27.60 2.67 6 2 -11 19.78 2.44 6 2 -11 14.52 1.95 6 -2 -11 13.09 1.95 6 2 -10 31.41 3.11 6 -2 -10 28.96 3.09 6 2 -9 83.96 5.36 6 -2 -9 79.18 5.36 6 2 -8 179.97 8.24 6 -2 -8 179.81 8.32 6 2 -7 199.81 9.89 6 -2 -7 209.29 6.10 6 2 -7 155.43 7.94 6 -2 -7 152.56 7.64 6 2 -6 428.06 14.61 6 -2 -6 342.89 11.39 6 2 -5 17.45 3.00 6 -2 -5 14.05 2.28 6 2 -4 295.61 12.20 6 -2 -4 278.11 10.30 6 2 -3 25.65 2.56 6 -2 -3 33.94 3.68 6 2 -2 834.68 20.27 6 2 -2 861.30 14.02 6 -2 -1 16.26 2.46 6 2 -1 16.39 2.81 6 2 -1 22.88 2.32 6 -2 -1 15.83 2.57 6 -2 0 164.91 7.84 6 2 0 156.91 8.23 6 2 0 161.34 5.91 6 -2 1 79.53 5.44 6 2 1 70.10 5.24 6 2 1 77.43 4.00 6 -2 1 70.97 5.80 6 2 2 575.70 14.20 6 -2 2 561.92 14.44 6 2 2 577.41 10.44 6 -2 3 104.82 6.19 6 -2 3 95.85 8.24 6 -2 4 2.24 1.31 6 -2 4 1.45 0.59 6 -2 5 20.03 2.63 6 -2 5 33.11 4.38 6 -2 6 87.23 5.30 6 -2 6 66.50 5.80 6 -2 7 12.75 1.88 6 -2 7 9.91 2.29 6 -2 8 95.01 6.40 6 -2 9 46.41 4.21 6 -2 10 21.68 2.62 6 -2 11 5.04 1.12 6 -2 12 5.62 1.05 6 3 -12 25.21 2.09 6 3 -11 80.10 4.32 6 3 -10 14.05 2.03 6 3 -9 2.51 0.94 6 3 -8 35.67 3.78 6 3 -7 98.24 6.56 6 3 -6 119.80 7.40 6 3 -5 94.45 6.61 6 3 -4 323.49 12.08 6 3 -3 406.75 13.59 6 -3 -3 387.03 10.66 6 -3 -2 134.32 6.67 6 3 -2 122.07 7.44 6 -3 -2 113.25 5.82 6 -3 -1 74.17 5.06 6 3 -1 69.47 5.48 6 -3 0 256.30 9.52 6 3 0 243.58 9.73 6 3 1 81.20 5.25 6 -3 1 84.65 5.43 6 -3 1 83.49 5.58 6 -3 2 128.23 6.63 6 -3 2 157.94 7.91 6 -3 3 175.59 7.73 6 -3 3 216.46 9.29 6 -3 4 135.09 6.65 6 -3 4 114.82 6.61 6 -3 5 18.31 2.39 6 -3 5 17.67 2.59 6 -3 6 5.05 1.40 6 -3 6 3.28 0.94 6 -3 7 39.78 3.12 6 -3 7 26.30 2.93 6 -3 8 77.43 3.89 6 -3 8 50.49 3.77 6 -3 9 2.99 0.81 6 -3 10 28.84 2.19 6 4 -10 10.37 1.33 6 4 -9 6.98 1.22 6 4 -8 7.72 1.39 6 4 -7 32.56 3.02 6 4 -6 19.51 2.44 6 4 -5 31.62 3.18 6 4 -4 12.73 2.04 6 4 -3 16.86 2.33 6 -4 -2 19.34 2.21 6 4 -2 16.11 2.23 6 -4 -1 6.45 1.33 6 4 -1 4.98 1.14 6 -4 0 93.16 5.12 6 -4 1 17.65 2.27 6 -4 1 17.47 1.89 6 -4 2 3.50 0.97 6 -4 2 5.12 1.06 6 -4 3 26.66 2.68 6 -4 3 21.61 1.98 6 -4 4 22.56 2.39 6 -4 4 17.48 1.71 6 -4 5 9.02 1.46 6 -4 5 8.19 1.08 6 -4 6 12.85 1.59 6 -4 7 79.44 3.60 6 -5 1 57.66 3.01 6 -5 2 5.72 0.94 6 -5 3 71.28 3.22 6 -5 4 5.61 0.85 7 0 -10 22.23 2.55 7 0 -9 23.04 2.80 7 0 -8 9.96 1.97 7 0 -7 7.09 1.14 7 0 -6 41.62 2.73 7 0 -5 16.05 1.77 7 0 -4 24.83 2.25 7 0 -3 144.70 5.50 7 0 -3 129.67 5.43 7 0 -2 239.21 7.08 7 0 -2 195.01 6.83 7 0 -1 15.38 1.78 7 0 -1 12.50 1.80 7 0 0 483.28 10.04 7 0 0 453.05 11.66 7 0 1 135.34 5.24 7 0 1 122.72 6.28 7 0 2 232.02 6.71 7 0 2 211.57 8.51 7 0 3 6.26 1.42 7 0 3 6.90 1.12 7 0 4 44.15 2.67 7 0 4 33.94 3.50 7 0 5 1.10 0.83 7 0 6 0.66 0.64 7 0 7 41.73 3.65 7 0 8 0.72 0.53 7 0 9 137.74 5.77 7 0 10 65.11 3.55 7 -1 -10 39.61 3.20 7 -1 -9 72.20 4.64 7 1 -8 17.36 2.15 7 -1 -8 19.68 1.60 7 1 -7 64.28 4.47 7 -1 -7 65.27 3.17 7 1 -6 21.21 2.66 7 -1 -6 22.71 1.98 7 1 -5 78.18 5.27 7 1 -5 88.90 4.22 7 -1 -5 75.11 3.68 7 1 -4 132.33 6.89 7 1 -4 148.74 5.54 7 -1 -4 129.30 5.00 7 1 -3 6.80 1.64 7 1 -3 7.30 1.24 7 -1 -3 6.15 1.06 7 -1 -3 5.93 1.25 7 -1 -2 4.23 1.04 7 -1 -2 3.10 0.73 7 1 -1 140.37 5.30 7 -1 -1 136.63 6.54 7 1 0 15.22 1.73 7 -1 0 14.12 2.19 7 1 1 121.90 4.78 7 -1 1 101.11 5.90 7 1 2 24.86 2.07 7 -1 2 29.27 3.56 7 1 3 31.17 2.17 7 -1 3 32.53 3.58 7 -1 4 37.59 3.84 7 -1 5 52.59 2.98 7 -1 5 43.58 4.08 7 -1 6 6.30 1.56 7 -1 7 33.66 3.35 7 -1 8 13.74 2.00 7 -1 9 143.14 5.98 7 -1 10 1.17 0.48 7 2 -10 55.13 2.89 7 2 -9 37.33 2.79 7 2 -8 74.49 4.35 7 2 -7 73.70 4.65 7 -2 -7 85.66 3.18 7 2 -6 254.86 9.06 7 -2 -6 261.58 6.02 7 2 -5 4.56 1.20 7 -2 -5 1.45 0.45 7 2 -4 88.53 5.53 7 -2 -4 86.52 3.95 7 2 -3 195.51 8.27 7 -2 -3 175.78 6.67 7 2 -2 14.05 2.21 7 -2 -2 11.38 1.74 7 -2 -1 43.59 3.39 7 -2 0 3.42 0.96 7 -2 1 21.62 2.96 7 -2 2 18.03 2.95 7 -2 3 61.32 4.41 7 -2 4 122.76 6.26 7 -2 5 23.79 2.73 7 -2 6 8.20 1.48 7 -2 7 10.78 1.62 7 -2 8 0.33 0.28 7 -2 9 6.44 1.02 7 3 -8 53.49 3.11 7 3 -7 80.16 4.15 7 3 -6 72.21 4.19 7 3 -5 53.44 3.73 7 -3 -5 58.02 2.51 7 3 -4 21.25 2.39 7 -3 -4 28.20 1.93 7 3 -3 29.86 2.85 7 3 -2 239.78 7.80 7 -3 0 42.83 3.43 7 -3 1 2.99 0.85 7 -3 2 12.67 1.58 7 -3 3 15.37 1.73 7 -3 4 5.18 1.06 7 -3 5 25.72 2.09 7 -3 6 4.74 0.86 8 0 -3 73.89 3.10 8 0 -2 75.06 3.14 8 0 -1 13.07 1.31 8 0 0 4.14 0.77 8 0 1 8.71 1.04 8 0 2 5.77 0.84 8 0 2 39.68 2.20 8 -1 -5 145.10 3.80 8 -1 -4 16.63 1.36 8 -1 -3 66.60 2.85 8 -1 -2 40.56 2.27 8 -1 -1 16.69 1.46 8 -1 0 5.89 0.89 8 -1 1 44.45 2.33 8 -1 1 55.04 2.85 8 -1 2 46.35 2.26 8 -1 2 38.79 2.33 8 -1 3 3.11 0.57 8 -1 3 40.42 2.40 8 -1 4 20.37 1.61 8 -2 -3 8.52 0.88 8 -2 -2 12.13 1.10 8 -2 -1 9.38 0.97 8 -2 0 23.05 1.52 8 -2 1 5.10 0.70 8 -2 2 3.09 0.52 8 -2 2 4.59 0.76 0 0 0 0.00 0.00 TITL 179-4 in P2(1)/m REM P2(1)/m (#11 in standard setting) CELL 1.54184 6.785606 6.044200 16.629247 90.0000 92.6827 90.0000 ZERR 3.00 0.000358 0.000357 0.000905 0.0000 0.0049 0.0000 LATT 1 SYMM -x, y+1/2,-z SFAC C H N O UNIT 33.00 30.00 3.00 3.00 TREF HKLF 4 END _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' ; _shelx_hkl_checksum 39389 _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 1.502 _oxdiff_exptl_absorpt_empirical_full_min 0.480