#------------------------------------------------------------------------------ #$Date: 2023-10-27 01:36:08 +0300 (Fri, 27 Oct 2023) $ #$Revision: 287127 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247581.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7247581 loop_ _publ_author_name 'Sobczak, Paulina' 'Siera\'nski, Tomasz' 'Swiatkowski, Marcin' 'Trzesowska-Kruszynska, Agata' _publ_section_title ; New Schiff base salts as sources of blue and green light in the solid state: the role of anion and protonation ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00758H _journal_year 2023 _chemical_formula_moiety 'C15 H14 N O3, H O4 S' _chemical_formula_sum 'C15 H15 N O7 S' _chemical_formula_weight 353.34 _space_group_crystal_system monoclinic _space_group_IT_number 7 _space_group_name_Hall 'P -2yc' _space_group_name_H-M_alt 'P 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2023-07-28 _audit_creation_method ; Olex2 1.5-ac5-024 (compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498) ; _audit_update_record ; 2023-07-28 deposited with the CCDC. 2023-10-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.109(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 4.47140(10) _cell_length_b 9.3275(2) _cell_length_c 17.7797(5) _cell_measurement_reflns_used 12883 _cell_measurement_temperature 100.0(1) _cell_measurement_theta_max 78.7550 _cell_measurement_theta_min 4.7330 _cell_volume 741.54(3) _computing_cell_refinement 'CrysAlisPro 1.171.42.86a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.86a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.86a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100.0(1) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_detector_type 'Pilatus 300K' _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.976 _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 -120.00 -33.00 0.50 6.00 -- -48.87 -57.00 -30.00 174 2 \w -120.00 -41.00 0.50 6.00 -- -48.87-178.00-180.00 158 3 \w -41.00 27.00 0.50 6.00 -- -48.87 38.00 120.00 136 4 \w -20.00 27.00 0.50 6.00 -- -48.87 19.00-150.00 94 5 \w 25.00 114.00 0.50 6.00 -- 48.87 77.00 30.00 178 6 \w -27.00 20.00 0.50 6.00 -- 48.87 -19.00 0.00 94 7 \w -41.00 -13.00 0.50 16.00 -- -88.50 38.00-180.00 56 8 \w -41.00 -13.00 0.50 16.00 -- -88.50 38.00 150.00 56 9 \w -87.00 -19.00 0.50 16.00 -- -88.50 125.00 90.00 136 10 \w -164.00 -75.00 0.50 16.00 -- -88.50 -38.00-150.00 178 11 \w -41.00 -13.00 0.50 16.00 -- -88.50 38.00 90.00 56 12 \w -87.00 -19.00 0.50 16.00 -- -88.50 125.00-150.00 136 13 \w -160.00 -16.00 0.50 16.00 -- -88.50 0.00-150.00 288 14 \w -157.00 -85.00 0.50 16.00 -- -88.50 -99.00-150.00 144 15 \w -41.00 -13.00 0.50 16.00 -- -88.50 38.00 120.00 56 16 \w -41.00 -13.00 0.50 16.00 -- -88.50 38.00 -60.00 56 17 \w -87.00 -19.00 0.50 16.00 -- -88.50 125.00 150.00 136 18 \w 86.00 176.00 0.50 16.00 -- 110.00 77.00 30.00 180 19 \w 38.00 66.00 0.50 16.00 -- 110.00 -57.00 120.00 56 20 \w 41.00 113.00 0.50 16.00 -- 110.00-125.00 60.00 144 21 \w 41.00 106.00 0.50 16.00 -- 110.00 -99.00 0.00 130 22 \w 41.00 106.00 0.50 16.00 -- 110.00 -99.00-120.00 130 23 \w 94.00 178.00 0.50 16.00 -- 110.00 125.00 60.00 168 24 \w 45.00 134.00 0.50 16.00 -- 110.00 -77.00 60.00 178 25 \w 41.00 106.00 0.50 16.00 -- 110.00 -99.00 90.00 130 26 \w 41.00 106.00 0.50 16.00 -- 110.00 -99.00-180.00 130 27 \w 38.00 66.00 0.50 16.00 -- 110.00 -57.00 -90.00 56 28 \w 25.00 114.00 0.50 6.00 -- 48.87 77.00-120.00 178 29 \w 25.00 114.00 0.50 6.00 -- 48.87 77.00 0.00 178 30 \w 25.00 114.00 0.50 6.00 -- 48.87 77.00 120.00 178 31 \w 25.00 114.00 0.50 6.00 -- 48.87 77.00 -90.00 178 32 \w 33.00 121.00 0.50 6.00 -- 48.87 57.00 90.00 176 33 \w 25.00 114.00 0.50 6.00 -- 48.87 77.00 150.00 178 34 \w -154.00 -65.00 0.50 16.00 -- -88.50 -77.00 30.00 178 35 \w -154.00 -65.00 0.50 16.00 -- -88.50 -77.00-180.00 178 36 \w -154.00 -65.00 0.50 16.00 -- -88.50 -77.00 120.00 178 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, Pilatus 300K' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0331452000 _diffrn_orient_matrix_UB_12 -0.0456742000 _diffrn_orient_matrix_UB_13 0.0828592000 _diffrn_orient_matrix_UB_21 0.3417892000 _diffrn_orient_matrix_UB_22 -0.0083829000 _diffrn_orient_matrix_UB_23 -0.0097371000 _diffrn_orient_matrix_UB_31 0.0276038000 _diffrn_orient_matrix_UB_32 0.1585269000 _diffrn_orient_matrix_UB_33 0.0233726000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_unetI/netI 0.0161 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 24898 _diffrn_reflns_point_group_measured_fraction_full 0.980 _diffrn_reflns_point_group_measured_fraction_max 0.925 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.665 _diffrn_reflns_theta_min 4.741 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.327 _exptl_absorpt_correction_T_max 0.955 _exptl_absorpt_correction_T_min 0.729 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.86a (Rigaku Oxford Diffraction, 2023) 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_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.582 _exptl_crystal_description prism _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.054 _exptl_crystal_size_min 0.024 _refine_diff_density_max 0.226 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.393(18) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 2993 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.073 _refine_ls_R_factor_all 0.0265 _refine_ls_R_factor_gt 0.0260 _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^)+(0.0432P)^2^+0.2527P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0708 _refine_ls_wR_factor_ref 0.0711 _reflns_Friedel_coverage 0.890 _reflns_Friedel_fraction_full 0.972 _reflns_Friedel_fraction_max 0.874 _reflns_number_gt 2972 _reflns_number_total 2993 _reflns_threshold_expression 'I > 2\s(I)' _twin_special_details ; Component 2 rotated by 55.3443\% around [-1.00 0.00 0.01] (reciprocal) or [-1.00 0.00 -0.00] (direct) ; _cod_data_source_file d3ce00758h2.cif _cod_data_source_block ps10_s04_2_twin1_hklf4 _cod_database_code 7247581 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C15 H15 N1 O7 S1' _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. ; _shelx_estimated_absorpt_t_max 0.946 _shelx_estimated_absorpt_t_min 0.617 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.607(18) 0.393(18) 2. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 3.a Aromatic/amide H refined with riding coordinates: N1(H1), C10(H10), C13(H13), C8(H8), C14(H14), C11(H11), C3(H3), C7(H7), C6(H6), C4(H4) 3.b Idealised Me refined as rotating group: C15(H15A,H15B,H15C) 3.c Idealised tetrahedral OH refined as rotating group: O2(H2), O7(H7A) ; _shelx_res_file ; TITL ps10_s04_2_twin1_hklf4_a.res in Pc ps10_s04_2_twin1_hklf4.res created by SHELXL-2018/3 at 13:12:41 on 28-Jul-2023 REM Old TITL ps10_s04_2_twin1_hklf4 in Pc REM SHELXT solution in Pc: R1 0.062, Rweak 0.034, Alpha 0.002 REM 0.000 for 0 systematic absences, Orientation as input REM Flack x = 0.409 ( 0.010 ) from 1369 Parsons' quotients REM Formula found by SHELXT: C15 N O7 S CELL 1.54184 4.4714 9.3275 17.7797 90 90.109 90 ZERR 2 0.0001 0.0002 0.0005 0 0.002 0 LATT -1 SYMM +X,-Y,0.5+Z SFAC C H N O S UNIT 30 30 2 14 2 L.S. 10 PLAN 20 SIZE 0.024 0.054 0.23 TEMP -173.15(10) CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta TWIN -1 0 0 0 -1 0 0 0 -1 2 REM REM REM WGHT 0.043200 0.252700 BASF 0.39340 FVAR 0.60926 S1 5 -0.462960 0.768363 0.865091 11.00000 0.01602 0.01330 = 0.01800 -0.00196 0.00403 0.00082 O3 4 1.587543 0.635393 0.122594 11.00000 0.02485 0.01841 = 0.01944 -0.00059 0.00722 0.00167 O6 4 -0.237753 0.880774 0.878504 11.00000 0.01668 0.01247 = 0.03480 -0.00100 0.00317 -0.00127 O5 4 -0.341254 0.629181 0.883523 11.00000 0.02735 0.01082 = 0.03018 -0.00049 0.00495 -0.00018 O2 4 -0.244553 0.706581 0.673398 11.00000 0.02738 0.01822 = 0.02124 -0.00104 0.01162 -0.00153 AFIX 147 H2 2 -0.347554 0.736770 0.709546 11.00000 -1.50000 AFIX 0 O1 4 -0.179703 0.940888 0.652465 11.00000 0.03504 0.01686 = 0.02890 -0.00324 0.01356 0.00165 O4 4 -0.594497 0.778118 0.790577 11.00000 0.02361 0.03296 = 0.01732 -0.00161 0.00355 0.00202 O7 4 -0.714899 0.798239 0.922962 11.00000 0.01618 0.03645 = 0.02007 -0.00240 0.00563 0.00235 AFIX 147 H7A 2 -0.871630 0.822341 0.900115 11.00000 -1.50000 AFIX 0 N1 3 0.646641 0.671174 0.395222 11.00000 0.01569 0.01294 = 0.01801 0.00012 0.00071 0.00043 AFIX 43 H1 2 0.667088 0.579292 0.385241 11.00000 -1.20000 AFIX 0 C9 1 1.011837 0.724438 0.298192 11.00000 0.01305 0.01598 = 0.01601 0.00045 -0.00205 0.00038 C10 1 1.152545 0.839375 0.260449 11.00000 0.01841 0.01295 = 0.01843 0.00085 -0.00098 0.00106 AFIX 43 H10 2 1.110216 0.935086 0.275275 11.00000 -1.20000 AFIX 0 C13 1 1.277337 0.557917 0.219225 11.00000 0.01829 0.01486 = 0.02219 -0.00077 -0.00072 0.00079 AFIX 43 H13 2 1.325190 0.462290 0.205341 11.00000 -1.20000 AFIX 0 C8 1 0.804593 0.761785 0.355448 11.00000 0.01562 0.01449 = 0.01708 0.00018 -0.00181 0.00016 AFIX 43 H8 2 0.778415 0.860930 0.365746 11.00000 -1.20000 AFIX 0 C5 1 0.443979 0.710461 0.453507 11.00000 0.01386 0.01534 = 0.01477 0.00006 0.00043 -0.00011 C14 1 1.081068 0.582180 0.276786 11.00000 0.01772 0.01438 = 0.01916 0.00123 0.00162 -0.00081 AFIX 43 H14 2 0.991526 0.503719 0.302308 11.00000 -1.20000 AFIX 0 C12 1 1.409563 0.673570 0.180224 11.00000 0.01584 0.01940 = 0.01440 -0.00058 0.00063 0.00114 C2 1 0.060858 0.774814 0.571368 11.00000 0.01539 0.01642 = 0.01549 -0.00143 0.00080 0.00081 C11 1 1.351100 0.814718 0.202210 11.00000 0.01839 0.01821 = 0.01652 0.00295 0.00080 -0.00031 AFIX 43 H11 2 1.446299 0.892623 0.177529 11.00000 -1.20000 AFIX 0 C3 1 0.197465 0.884273 0.530506 11.00000 0.02034 0.01208 = 0.02499 -0.00282 0.00321 0.00126 AFIX 43 H3 2 0.158542 0.981432 0.543178 11.00000 -1.20000 AFIX 0 C7 1 0.111355 0.631866 0.551574 11.00000 0.01846 0.01498 = 0.01710 0.00233 0.00138 -0.00171 AFIX 43 H7 2 0.014721 0.556991 0.578386 11.00000 -1.20000 AFIX 0 C6 1 0.303405 0.599478 0.492531 11.00000 0.01956 0.01220 = 0.01856 -0.00013 0.00068 0.00043 AFIX 43 H6 2 0.338716 0.502503 0.478842 11.00000 -1.20000 AFIX 0 C15 1 1.714692 0.747253 0.076973 11.00000 0.02584 0.02320 = 0.01823 0.00222 0.00573 -0.00024 AFIX 137 H15A 2 1.835896 0.704459 0.036969 11.00000 -1.50000 H15B 2 1.841014 0.809005 0.108328 11.00000 -1.50000 H15C 2 1.553741 0.804461 0.054558 11.00000 -1.50000 AFIX 0 C1 1 -0.133101 0.816621 0.635903 11.00000 0.01771 0.01572 = 0.01889 -0.00101 0.00118 -0.00046 C4 1 0.388866 0.853030 0.471773 11.00000 0.01946 0.01341 = 0.02300 0.00176 0.00357 -0.00030 AFIX 43 H4 2 0.481652 0.928040 0.444215 11.00000 -1.20000 AFIX 0 HKLF 4 REM ps10_s04_2_twin1_hklf4_a.res in Pc REM wR2 = 0.0711, GooF = S = 1.073, Restrained GooF = 1.073 for all data REM R1 = 0.0260 for 2972 Fo > 4sig(Fo) and 0.0265 for all 2993 data REM 221 parameters refined using 2 restraints END WGHT 0.0434 0.2451 REM Highest difference peak 0.226, deepest hole -0.202, 1-sigma level 0.045 Q1 1 1.3134 0.6164 0.2044 11.00000 0.05 0.23 Q2 1 0.4153 0.7778 0.4618 11.00000 0.05 0.22 Q3 1 1.0334 0.6553 0.2854 11.00000 0.05 0.22 Q4 1 1.4023 0.7404 0.1978 11.00000 0.05 0.22 Q5 1 0.1418 0.8310 0.5565 11.00000 0.05 0.21 Q6 1 0.0581 0.7050 0.5605 11.00000 0.05 0.20 Q7 1 0.2858 0.8632 0.5004 11.00000 0.05 0.20 Q8 1 0.9426 0.7352 0.3362 11.00000 0.05 0.19 Q9 1 -0.0252 0.7873 0.5965 11.00000 0.05 0.19 Q10 1 -0.4275 0.5655 0.8798 11.00000 0.05 0.18 Q11 1 1.6180 0.8984 0.1168 11.00000 0.05 0.18 Q12 1 0.2430 0.6226 0.5210 11.00000 0.05 0.17 Q13 1 1.0497 0.7741 0.2752 11.00000 0.05 0.16 Q14 1 0.3475 0.6585 0.4663 11.00000 0.05 0.16 Q15 1 1.2331 0.8203 0.2341 11.00000 0.05 0.16 Q16 1 -0.6755 0.7776 0.9636 11.00000 0.05 0.16 Q17 1 -0.2545 0.8450 0.8776 11.00000 0.05 0.16 Q18 1 0.5647 0.6986 0.4232 11.00000 0.05 0.16 Q19 1 1.7550 0.8773 0.0966 11.00000 0.05 0.15 Q20 1 1.6669 0.5626 0.1173 11.00000 0.05 0.15 ; _shelx_res_checksum 91624 _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 1.877 _oxdiff_exptl_absorpt_empirical_full_min 0.526 _oxdiff_twin_integration_method simultaneous _oxdiff_twin_items 2 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, z+1/2' 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 -0.46296(12) 0.76836(5) 0.86509(4) 0.01577(14) Uani 1 1 d . . . . . O3 O 1.5875(4) 0.63539(19) 0.12259(10) 0.0209(4) Uani 1 1 d . . . . . O6 O -0.2378(4) 0.88077(18) 0.87850(11) 0.0213(4) Uani 1 1 d . . . . . O5 O -0.3413(4) 0.62918(18) 0.88352(11) 0.0228(4) Uani 1 1 d . . . . . O2 O -0.2446(4) 0.70658(19) 0.67340(11) 0.0223(4) Uani 1 1 d . . . . . H2 H -0.347554 0.736770 0.709546 0.033 Uiso 1 1 calc R U . . . O1 O -0.1797(4) 0.9409(2) 0.65246(11) 0.0269(4) Uani 1 1 d . . . . . O4 O -0.5945(4) 0.7781(2) 0.79058(11) 0.0246(4) Uani 1 1 d . . . . . O7 O -0.7149(4) 0.7982(2) 0.92296(11) 0.0242(4) Uani 1 1 d . . . . . H7A H -0.871630 0.822341 0.900115 0.036 Uiso 1 1 calc R U . . . N1 N 0.6466(4) 0.6712(2) 0.39522(11) 0.0155(4) Uani 1 1 d . . . . . H1 H 0.667088 0.579292 0.385241 0.019 Uiso 1 1 calc R U . . . C9 C 1.0118(5) 0.7244(3) 0.29819(14) 0.0150(5) Uani 1 1 d . . . . . C10 C 1.1525(5) 0.8394(3) 0.26045(14) 0.0166(5) Uani 1 1 d . . . . . H10 H 1.110216 0.935086 0.275275 0.020 Uiso 1 1 calc R U . . . C13 C 1.2773(5) 0.5579(3) 0.21922(15) 0.0184(5) Uani 1 1 d . . . . . H13 H 1.325190 0.462290 0.205341 0.022 Uiso 1 1 calc R U . . . C8 C 0.8046(5) 0.7618(3) 0.35545(14) 0.0157(5) Uani 1 1 d . . . . . H8 H 0.778415 0.860930 0.365746 0.019 Uiso 1 1 calc R U . . . C5 C 0.4440(5) 0.7105(3) 0.45351(13) 0.0147(4) Uani 1 1 d . . . . . C14 C 1.0811(5) 0.5822(3) 0.27679(14) 0.0171(5) Uani 1 1 d . . . . . H14 H 0.991526 0.503719 0.302308 0.021 Uiso 1 1 calc R U . . . C12 C 1.4096(5) 0.6736(3) 0.18022(14) 0.0165(5) Uani 1 1 d . . . . . C2 C 0.0609(5) 0.7748(3) 0.57137(14) 0.0158(5) Uani 1 1 d . . . . . C11 C 1.3511(5) 0.8147(3) 0.20221(14) 0.0177(5) Uani 1 1 d . . . . . H11 H 1.446299 0.892623 0.177529 0.021 Uiso 1 1 calc R U . . . C3 C 0.1975(5) 0.8843(3) 0.53051(14) 0.0191(5) Uani 1 1 d . . . . . H3 H 0.158542 0.981432 0.543178 0.023 Uiso 1 1 calc R U . . . C7 C 0.1114(5) 0.6319(3) 0.55157(14) 0.0168(5) Uani 1 1 d . . . . . H7 H 0.014721 0.556991 0.578386 0.020 Uiso 1 1 calc R U . . . C6 C 0.3034(5) 0.5995(3) 0.49253(14) 0.0168(5) Uani 1 1 d . . . . . H6 H 0.338716 0.502503 0.478842 0.020 Uiso 1 1 calc R U . . . C15 C 1.7147(6) 0.7473(3) 0.07697(16) 0.0224(5) Uani 1 1 d . . . . . H15A H 1.835896 0.704459 0.036969 0.034 Uiso 1 1 calc R U . . . H15B H 1.841014 0.809005 0.108328 0.034 Uiso 1 1 calc R U . . . H15C H 1.553741 0.804461 0.054558 0.034 Uiso 1 1 calc R U . . . C1 C -0.1331(5) 0.8166(3) 0.63590(14) 0.0174(5) Uani 1 1 d . . . . . C4 C 0.3889(5) 0.8530(3) 0.47177(15) 0.0186(5) Uani 1 1 d . . . . . H4 H 0.481652 0.928040 0.444215 0.022 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0160(2) 0.0133(2) 0.0180(3) -0.0020(3) 0.00403(18) 0.0008(2) O3 0.0249(9) 0.0184(8) 0.0194(9) -0.0006(7) 0.0072(7) 0.0017(7) O6 0.0167(8) 0.0125(8) 0.0348(10) -0.0010(7) 0.0032(7) -0.0013(6) O5 0.0274(9) 0.0108(8) 0.0302(10) -0.0005(7) 0.0049(8) -0.0002(7) O2 0.0274(10) 0.0182(9) 0.0212(9) -0.0010(7) 0.0116(7) -0.0015(7) O1 0.0350(10) 0.0169(9) 0.0289(10) -0.0032(8) 0.0136(8) 0.0016(8) O4 0.0236(10) 0.0330(10) 0.0173(9) -0.0016(8) 0.0035(7) 0.0020(8) O7 0.0162(8) 0.0364(11) 0.0201(10) -0.0024(8) 0.0056(7) 0.0023(8) N1 0.0157(9) 0.0129(9) 0.0180(10) 0.0001(7) 0.0007(8) 0.0004(7) C9 0.0130(11) 0.0160(11) 0.0160(11) 0.0004(9) -0.0021(9) 0.0004(8) C10 0.0184(11) 0.0129(11) 0.0184(12) 0.0009(9) -0.0010(9) 0.0011(8) C13 0.0183(11) 0.0149(11) 0.0222(12) -0.0008(9) -0.0007(9) 0.0008(9) C8 0.0156(11) 0.0145(11) 0.0171(12) 0.0002(8) -0.0018(9) 0.0002(9) C5 0.0139(10) 0.0153(11) 0.0148(11) 0.0001(9) 0.0004(9) -0.0001(8) C14 0.0177(11) 0.0144(11) 0.0192(12) 0.0012(9) 0.0016(8) -0.0008(9) C12 0.0158(11) 0.0194(11) 0.0144(11) -0.0006(9) 0.0006(8) 0.0011(9) C2 0.0154(11) 0.0164(11) 0.0155(11) -0.0014(9) 0.0008(9) 0.0008(8) C11 0.0184(11) 0.0182(12) 0.0165(12) 0.0029(9) 0.0008(9) -0.0003(9) C3 0.0203(11) 0.0121(11) 0.0250(13) -0.0028(9) 0.0032(10) 0.0013(9) C7 0.0185(11) 0.0150(11) 0.0171(12) 0.0023(9) 0.0014(9) -0.0017(9) C6 0.0196(11) 0.0122(10) 0.0186(11) -0.0001(9) 0.0007(9) 0.0004(9) C15 0.0258(14) 0.0232(12) 0.0182(12) 0.0022(10) 0.0057(10) -0.0002(10) C1 0.0177(11) 0.0157(11) 0.0189(12) -0.0010(9) 0.0012(9) -0.0005(9) C4 0.0195(12) 0.0134(11) 0.0230(13) 0.0018(9) 0.0036(9) -0.0003(9) 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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -6 -3 0.0229 0 -5 7 0.0182 0 5 -7 0.0182 0 -6 -3 0.0173 -3 -1 -2 0.1055 2 4 3 0.0915 -3 1 -1 0.1105 3 -2 0 0.1062 0 1 -11 0.0133 0 5 8 0.0178 0 5 -8 0.0171 0 -5 6 0.0121 0 5 -6 0.0121 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 O6 S1 O7 105.17(11) . . ? O5 S1 O6 110.23(12) . . ? O5 S1 O4 114.53(11) . . ? O5 S1 O7 106.52(12) . . ? O4 S1 O6 112.27(11) . . ? O4 S1 O7 107.48(11) . . ? C12 O3 C15 118.2(2) . . ? C1 O2 H2 109.5 . . ? S1 O7 H7A 109.5 . . ? C8 N1 H1 117.6 . . ? C8 N1 C5 124.8(2) . . ? C5 N1 H1 117.6 . . ? C10 C9 C8 116.5(2) . . ? C10 C9 C14 119.1(2) . . ? C14 C9 C8 124.5(2) . . ? C9 C10 H10 119.5 . . ? C11 C10 C9 121.1(2) . . ? C11 C10 H10 119.5 . . ? C14 C13 H13 119.7 . . ? C14 C13 C12 120.7(2) . . ? C12 C13 H13 119.7 . . ? N1 C8 C9 125.6(2) . . ? N1 C8 H8 117.2 . . ? C9 C8 H8 117.2 . . ? C6 C5 N1 117.3(2) . . ? C4 C5 N1 121.9(2) . . ? C4 C5 C6 120.8(2) . . ? C9 C14 H14 120.1 . . ? C13 C14 C9 119.8(2) . . ? C13 C14 H14 120.1 . . ? O3 C12 C13 114.8(2) . . ? O3 C12 C11 124.9(2) . . ? C11 C12 C13 120.2(2) . . ? C3 C2 C7 119.7(2) . . ? C3 C2 C1 117.7(2) . . ? C7 C2 C1 122.5(2) . . ? C10 C11 C12 119.1(2) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C2 C3 H3 119.6 . . ? C4 C3 C2 120.8(2) . . ? C4 C3 H3 119.6 . . ? C2 C7 H7 120.1 . . ? C6 C7 C2 119.8(2) . . ? C6 C7 H7 120.1 . . ? C5 C6 H6 120.2 . . ? C7 C6 C5 119.6(2) . . ? C7 C6 H6 120.2 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O2 C1 C2 113.9(2) . . ? O1 C1 O2 123.6(2) . . ? O1 C1 C2 122.4(2) . . ? C5 C4 H4 120.4 . . ? C3 C4 C5 119.2(2) . . ? C3 C4 H4 120.4 . . ? 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 O6 1.4729(18) . ? S1 O5 1.4451(19) . ? S1 O4 1.451(2) . ? S1 O7 1.5524(18) . ? O3 C12 1.347(3) . ? O3 C15 1.439(3) . ? O2 H2 0.8400 . ? O2 C1 1.322(3) . ? O1 C1 1.214(3) . ? O7 H7A 0.8400 . ? N1 H1 0.8800 . ? N1 C8 1.310(3) . ? N1 C5 1.426(3) . ? C9 C10 1.413(3) . ? C9 C8 1.421(3) . ? C9 C14 1.415(3) . ? C10 H10 0.9500 . ? C10 C11 1.384(4) . ? C13 H13 0.9500 . ? C13 C14 1.368(4) . ? C13 C12 1.413(4) . ? C8 H8 0.9500 . ? C5 C6 1.396(3) . ? C5 C4 1.391(3) . ? C14 H14 0.9500 . ? C12 C11 1.398(4) . ? C2 C3 1.395(3) . ? C2 C7 1.397(3) . ? C2 C1 1.491(3) . ? C11 H11 0.9500 . ? C3 H3 0.9500 . ? C3 C4 1.382(4) . ? C7 H7 0.9500 . ? C7 C6 1.391(3) . ? C6 H6 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C4 H4 0.9500 . ? 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 O3 C12 C11 C10 177.1(2) . . . . ? N1 C5 C6 C7 177.9(2) . . . . ? N1 C5 C4 C3 -177.9(2) . . . . ? C9 C10 C11 C12 0.7(4) . . . . ? C10 C9 C8 N1 178.1(2) . . . . ? C10 C9 C14 C13 -1.3(4) . . . . ? C13 C12 C11 C10 -2.7(3) . . . . ? C8 N1 C5 C6 -177.2(2) . . . . ? C8 N1 C5 C4 2.2(3) . . . . ? C8 C9 C10 C11 -178.0(2) . . . . ? C8 C9 C14 C13 177.9(2) . . . . ? C5 N1 C8 C9 178.7(2) . . . . ? C14 C9 C10 C11 1.3(4) . . . . ? C14 C9 C8 N1 -1.1(4) . . . . ? C14 C13 C12 O3 -177.0(2) . . . . ? C14 C13 C12 C11 2.8(3) . . . . ? C12 C13 C14 C9 -0.7(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C2 C7 C6 C5 0.0(4) . . . . ? C3 C2 C7 C6 1.7(4) . . . . ? C3 C2 C1 O2 -177.5(2) . . . . ? C3 C2 C1 O1 1.7(4) . . . . ? C7 C2 C3 C4 -1.7(4) . . . . ? C7 C2 C1 O2 1.8(3) . . . . ? C7 C2 C1 O1 -179.1(2) . . . . ? C6 C5 C4 C3 1.5(4) . . . . ? C15 O3 C12 C13 176.0(2) . . . . ? C15 O3 C12 C11 -3.9(4) . . . . ? C1 C2 C3 C4 177.6(2) . . . . ? C1 C2 C7 C6 -177.6(2) . . . . ? C4 C5 C6 C7 -1.5(4) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined _oxdiff_twin_reflns_isolated _oxdiff_twin_reflns_overlapped _twin_individual_twin_lattice_type _twin_individual_twin_matrix_11 _twin_individual_twin_matrix_12 _twin_individual_twin_matrix_13 _twin_individual_twin_matrix_21 _twin_individual_twin_matrix_22 _twin_individual_twin_matrix_23 _twin_individual_twin_matrix_31 _twin_individual_twin_matrix_32 _twin_individual_twin_matrix_33 1 0.607(18) 11416 2874 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 2 0.393(18) 11501 2874 nmt 1.0000 -0.0001 0.0000 0.0025 0.5687 0.4314 -0.0031 -1.5676 0.5686 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 -0.0193 -5.8476 -2.9828 0.0193 0.0715 -0.9973 -0.4631 -4.8763 6.5924 0.7536 -0.1816 -0.6317 0.4631 4.8763 -6.5924 -0.7536 0.1816 0.6317 0.2163 -5.8489 -2.8493 0.0382 0.1507 -0.9878 -2.7712 -1.3453 -2.2614 -0.2178 -0.9139 -0.3426 2.0948 3.8476 3.1480 0.1545 0.6531 0.7414 -2.8344 1.1875 -1.0102 -0.2319 -0.9689 0.0864 2.6981 -2.2209 0.4074 0.2246 0.9368 -0.2681 0.3886 1.1931 -11.2131 -0.9707 0.2320 -0.0622 0.0383 4.5566 7.5955 0.4225 -0.0991 0.9009 -0.0447 4.5736 -7.5605 -0.8368 0.0200 0.5471 -0.0146 -5.2598 5.7154 0.7133 -0.0166 -0.7006 0.0146 5.2598 -5.7154 -0.7133 0.0166 0.7006