#------------------------------------------------------------------------------ #$Date: 2024-01-06 11:55:24 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288907 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247673.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_7247673 loop_ _publ_author_name 'Xiao, Xiao' 'Mu, Tong' 'Sukhanov, Andrey A.' 'Zhou, Yihang' 'Yu, Peiran' 'Yu, Fabiao' 'Elmali, Ayhan' 'Zhao, Jianzhang' 'Karatay, Ahmet' 'Voronkova, Violeta K.' _publ_section_title ; The effect of thionation of the carbonyl group on the photophysics of compact spiro rhodamine-naphthalimide electron donor-acceptor dyads: intersystem crossing, charge separation, and electron spin dynamics. ; _journal_issue 46 _journal_name_full 'Physical chemistry chemical physics : PCCP' _journal_page_first 31667 _journal_page_last 31682 _journal_paper_doi 10.1039/d3cp04891h _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C18 H18 N2 O S2' _chemical_formula_sum 'C18 H18 N2 O S2' _chemical_formula_weight 342.46 _chemical_name_systematic NIS-NHAc _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2023-09-08 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335) ; _audit_update_record ; 2023-09-11 deposited with the CCDC. 2023-11-01 downloaded from the CCDC. ; _cell_angle_alpha 76.969(2) _cell_angle_beta 75.0350(10) _cell_angle_gamma 72.6480(10) _cell_formula_units_Z 4 _cell_length_a 9.2114(4) _cell_length_b 13.4808(6) _cell_length_c 14.5200(7) _cell_measurement_reflns_used 5255 _cell_measurement_temperature 120 _cell_measurement_theta_max 26.54 _cell_measurement_theta_min 2.94 _cell_volume 1640.93(13) _computing_cell_refinement 'SAINT V8.40A (?, 2016)' _computing_data_reduction 'SAINT V8.40A (?, 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'SIR2004 (Burla et al., 2007)' _diffrn_ambient_temperature 120.0 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0645 _diffrn_reflns_av_unetI/netI 0.0556 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 26161 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.026 _diffrn_reflns_theta_max 25.026 _diffrn_reflns_theta_min 2.344 _exptl_absorpt_coefficient_mu 0.330 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6885 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1168 before and 0.0627 after correction. The Ratio of minimum to maximum transmission is 0.9237. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'metallic reddish red' _exptl_crystal_colour_lustre metallic _exptl_crystal_colour_modifier reddish _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.386 _exptl_crystal_description needle _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.528 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 419 _refine_ls_number_reflns 5766 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.025 _refine_ls_R_factor_all 0.0875 _refine_ls_R_factor_gt 0.0551 _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^)+(0.0585P)^2^+1.9559P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1271 _refine_ls_wR_factor_ref 0.1465 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4116 _reflns_number_total 5766 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL 1_a.res in P-1 1.res created by SHELXL-2016/6 at 21:37:19 on 08-Sep-2023 REM Old TITL 1 in P-1 REM SHELXT solution in P-1 REM R1 0.173, Rweak 0.011, Alpha 0.050, Orientation as input REM Formula found by SHELXT: C36 N4 O2 S4 CELL 0.71073 9.2114 13.4808 14.52 76.969 75.035 72.648 ZERR 4 0.0004 0.0006 0.0007 0.002 0.001 0.001 LATT 1 SFAC C H N O S UNIT 72 72 8 4 8 L.S. 20 PLAN 5 TEMP -153.15 BOND $H list 4 fmap 2 acta SHEL 999 0.84 REM REM REM WGHT 0.058500 1.955900 FVAR 0.70610 S001 5 0.181637 0.496137 -0.043076 11.00000 0.03637 0.05031 = 0.03920 -0.01202 -0.01110 -0.01471 S002 5 0.042741 0.227850 0.341319 11.00000 0.05571 0.03246 = 0.04786 -0.01234 -0.01038 -0.01199 S003 5 0.519780 0.196240 0.175379 11.00000 0.05259 0.02874 = 0.05762 -0.00778 -0.01706 -0.00909 S004 5 0.424721 0.282314 0.529235 11.00000 0.04935 0.04157 = 0.06019 -0.00210 -0.03105 -0.00079 O005 4 -0.307714 0.764100 0.221468 11.00000 0.02248 0.03351 = 0.04904 -0.00370 -0.01506 -0.01036 O006 4 0.138702 0.876729 0.231583 11.00000 0.01963 0.02474 = 0.06747 -0.01421 -0.01094 -0.00302 N007 3 -0.072645 0.750124 0.252629 11.00000 0.01911 0.02300 = 0.03979 -0.00479 -0.01008 -0.00799 AFIX 43 H007 2 -0.007873 0.786465 0.253152 11.00000 -1.20000 AFIX 0 N008 3 0.360157 0.357554 0.069023 11.00000 0.02637 0.03318 = 0.02917 -0.01043 -0.00260 -0.01358 N009 3 0.387875 0.776316 0.204241 11.00000 0.01535 0.02373 = 0.04506 -0.00723 -0.00864 -0.00424 AFIX 43 H009 2 0.482449 0.768997 0.211852 11.00000 -1.20000 AFIX 0 N00A 3 0.243922 0.271055 0.418308 11.00000 0.02965 0.02677 = 0.03530 -0.00837 -0.00726 0.00009 C00B 1 0.070551 0.601060 0.350444 11.00000 0.01570 0.02631 = 0.02765 -0.00803 -0.00251 -0.00388 C00C 1 0.408519 0.511281 0.153027 11.00000 0.01543 0.02598 = 0.02819 -0.00538 0.00025 -0.00919 C00D 1 0.362200 0.697000 0.165223 11.00000 0.01725 0.02013 = 0.03524 -0.00546 -0.00022 -0.00630 C00E 1 0.078268 0.421460 0.334988 11.00000 0.02001 0.02694 = 0.02605 -0.00861 -0.00005 -0.00655 C00F 1 0.314613 0.542399 0.082846 11.00000 0.01833 0.03073 = 0.02912 -0.00727 -0.00202 -0.00939 C00G 1 0.433902 0.589553 0.195048 11.00000 0.01598 0.02796 = 0.03019 -0.00492 -0.00048 -0.00826 C00H 1 -0.026330 0.641110 0.281138 11.00000 0.01760 0.02747 = 0.03181 -0.00704 -0.00556 -0.00666 C00I 1 0.477061 0.403664 0.181018 11.00000 0.02292 0.02474 = 0.02702 -0.00498 -0.00076 -0.00615 C00J 1 0.228492 0.448103 0.440338 11.00000 0.01977 0.03231 = 0.02552 -0.00683 -0.00164 -0.00436 C00K 1 0.126551 0.490071 0.374908 11.00000 0.01542 0.03053 = 0.02377 -0.00825 -0.00135 -0.00491 C00L 1 0.275988 0.863033 0.230715 11.00000 0.02621 0.02162 = 0.04764 -0.00755 -0.00687 -0.00730 C00M 1 0.528523 0.556552 0.264530 11.00000 0.02452 0.02870 = 0.02830 -0.00751 -0.00446 -0.00967 AFIX 43 H00M 2 0.545654 0.607340 0.293684 11.00000 -1.20000 AFIX 0 C00N 1 0.113615 0.666431 0.397024 11.00000 0.02100 0.03133 = 0.03343 -0.01404 -0.00161 -0.00583 AFIX 43 H00N 2 0.074935 0.740688 0.383403 11.00000 -1.20000 AFIX 0 C00O 1 -0.207678 0.805579 0.224193 11.00000 0.02470 0.03070 = 0.02933 -0.00481 -0.00612 -0.00850 C00P 1 -0.067665 0.572589 0.240973 11.00000 0.02538 0.02968 = 0.03808 -0.00616 -0.01383 -0.00742 AFIX 43 H00P 2 -0.131338 0.599551 0.194296 11.00000 -1.20000 AFIX 0 C00Q 1 0.570667 0.375286 0.249214 11.00000 0.02892 0.02611 = 0.03313 -0.00275 -0.00774 -0.00649 AFIX 43 H00Q 2 0.618038 0.303024 0.268126 11.00000 -1.20000 AFIX 0 C00R 1 0.210107 0.624226 0.461357 11.00000 0.02491 0.03599 = 0.03372 -0.01383 -0.00738 -0.00703 AFIX 43 H00R 2 0.237495 0.669466 0.491830 11.00000 -1.20000 AFIX 0 C00S 1 0.289951 0.462696 0.038489 11.00000 0.02095 0.03458 = 0.02980 -0.00923 0.00291 -0.01180 C00T 1 0.126631 0.308380 0.365492 11.00000 0.02779 0.03295 = 0.02372 -0.00921 0.00149 -0.00407 C00U 1 0.248064 0.647754 0.056305 11.00000 0.02312 0.03345 = 0.03484 -0.00385 -0.00837 -0.00695 AFIX 43 H00U 2 0.184657 0.668454 0.009529 11.00000 -1.20000 AFIX 0 C00V 1 0.271816 0.724168 0.096527 11.00000 0.02292 0.02806 = 0.03985 -0.00407 -0.00885 -0.00606 AFIX 43 H00V 2 0.225184 0.796302 0.076504 11.00000 -1.20000 AFIX 0 C00W 1 -0.016816 0.464597 0.268333 11.00000 0.02455 0.03068 = 0.03578 -0.01122 -0.00473 -0.00979 AFIX 43 H00W 2 -0.048063 0.418886 0.240587 11.00000 -1.20000 AFIX 0 C00X 1 0.595892 0.451540 0.290194 11.00000 0.02801 0.03299 = 0.03190 -0.00357 -0.01147 -0.00622 AFIX 43 H00X 2 0.660424 0.430449 0.336357 11.00000 -1.20000 AFIX 0 C00Y 1 0.268272 0.516144 0.482499 11.00000 0.02454 0.04349 = 0.02908 -0.00830 -0.00898 -0.00549 AFIX 43 H00Y 2 0.336417 0.488314 0.526548 11.00000 -1.20000 AFIX 0 C00Z 1 0.294488 0.334149 0.459934 11.00000 0.02726 0.03689 = 0.03279 -0.00711 -0.00287 -0.00419 C010 1 -0.226112 0.922154 0.196887 11.00000 0.03246 0.02601 = 0.04739 -0.00406 -0.01512 -0.00555 AFIX 137 H01M 2 -0.256368 0.946318 0.134012 11.00000 -1.50000 H01N 2 -0.127372 0.938034 0.192992 11.00000 -1.50000 H01O 2 -0.306639 0.958267 0.245818 11.00000 -1.50000 AFIX 0 C011 1 0.330586 0.277200 0.026393 11.00000 0.03930 0.03203 = 0.03330 -0.01346 -0.00018 -0.01765 AFIX 23 H01A 2 0.420490 0.214634 0.025393 11.00000 -1.20000 H01B 2 0.319018 0.306058 -0.041090 11.00000 -1.20000 AFIX 0 C012 1 0.449699 0.322560 0.139955 11.00000 0.02694 0.03018 = 0.03487 -0.01145 0.00318 -0.01043 C013 1 0.183536 0.244443 0.084290 11.00000 0.04104 0.04321 = 0.03467 -0.00774 -0.00391 -0.02350 AFIX 23 H01C 2 0.200240 0.207916 0.149407 11.00000 -1.20000 H01D 2 0.096573 0.308208 0.092213 11.00000 -1.20000 AFIX 0 C014 1 0.334862 0.942418 0.258923 11.00000 0.03545 0.03401 = 0.08469 -0.02891 -0.01682 -0.00686 AFIX 137 H01E 2 0.386003 0.981883 0.200714 11.00000 -1.50000 H01F 2 0.409475 0.905887 0.300640 11.00000 -1.50000 H01G 2 0.247439 0.991170 0.293780 11.00000 -1.50000 AFIX 0 C015 1 0.139898 0.172380 0.035513 11.00000 0.05823 0.05137 = 0.04577 -0.00662 -0.01274 -0.03401 AFIX 23 H01H 2 0.230353 0.111756 0.022485 11.00000 -1.20000 H01I 2 0.114891 0.211124 -0.027320 11.00000 -1.20000 AFIX 0 C016 1 0.311216 0.156227 0.434474 11.00000 0.04422 0.02961 = 0.05030 -0.01141 -0.01424 0.00667 AFIX 23 H01P 2 0.421520 0.142110 0.438224 11.00000 -1.20000 H01Q 2 0.308205 0.126932 0.378505 11.00000 -1.20000 AFIX 0 C017 1 0.227245 0.100591 0.525387 11.00000 0.07784 0.02901 = 0.04975 -0.00558 -0.02002 -0.00630 AFIX 23 H01R 2 0.113664 0.128762 0.530455 11.00000 -1.20000 H01S 2 0.254251 0.114212 0.582291 11.00000 -1.20000 AFIX 0 C018 1 0.002068 0.131685 0.095771 11.00000 0.06824 0.06313 = 0.06255 0.01112 -0.02576 -0.04346 AFIX 137 H01J 2 -0.025281 0.089397 0.059261 11.00000 -1.50000 H01K 2 -0.086750 0.191330 0.111229 11.00000 -1.50000 H01L 2 0.029241 0.088052 0.155731 11.00000 -1.50000 AFIX 0 C019 1 0.216047 -0.078746 0.613529 11.00000 0.07972 0.05628 = 0.06410 -0.00643 -0.01354 -0.01969 AFIX 137 H01T 2 0.228086 -0.150139 0.602547 11.00000 -1.50000 H01U 2 0.106054 -0.046589 0.637657 11.00000 -1.50000 H01V 2 0.276286 -0.081925 0.661231 11.00000 -1.50000 AFIX 0 C01A 1 0.270794 -0.017179 0.525203 11.00000 0.06220 0.04526 = 0.09483 0.01482 -0.00645 0.00541 AFIX 23 H01W 2 0.229724 -0.030028 0.473540 11.00000 -1.20000 H01X 2 0.385493 -0.041948 0.508684 11.00000 -1.20000 AFIX 0 HKLF 4 REM 1_a.res in P-1 REM R1 = 0.0551 for 4116 Fo > 4sig(Fo) and 0.0875 for all 5766 data REM 419 parameters refined using 0 restraints END WGHT 0.0585 1.9559 REM Highest difference peak 0.528, deepest hole -0.427, 1-sigma level 0.063 Q1 1 0.2514 -0.0945 0.5138 11.00000 0.05 0.53 Q2 1 0.2294 -0.0051 0.5936 11.00000 0.05 0.40 Q3 1 0.3175 -0.0131 0.5800 11.00000 0.05 0.39 Q4 1 0.1504 0.1231 0.5761 11.00000 0.05 0.38 Q5 1 0.2673 -0.0023 0.5023 11.00000 0.05 0.32 REM The information below was added by Olex2. REM REM R1 = 0.0551 for 4116 Fo > 4sig(Fo) and 0.0875 for all 29771 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.53, deepest hole -0.43 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0875 REM R1_gt = 0.0551 REM wR_ref = 0.1465 REM GOOF = 1.025 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 29771 REM Reflections_gt = 4116 REM Parameters = n/a REM Hole = -0.43 REM Peak = 0.53 REM Flack = n/a ; _cod_data_source_file d3cp04891h2.cif _cod_data_source_block 1 _cod_depositor_comments 'Adding full bibliography for 7247673--7247674.cif.' _cod_database_code 7247673 _shelx_shelxl_version_number 2016/6 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C011(H01A,H01B), C013(H01C,H01D), C015(H01H,H01I), C016(H01P,H01Q), C017(H01R, H01S), C01A(H01W,H01X) 2.b Aromatic/amide H refined with riding coordinates: N007(H007), N009(H009), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y) 2.c Idealised Me refined as rotating group: C010(H01M,H01N,H01O), C014(H01E,H01F,H01G), C018(H01J,H01K,H01L), C019(H01T, H01U,H01V) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 S001 S 0.18164(11) 0.49614(8) -0.04308(7) 0.0397(3) Uani 1 1 d . . . . . S002 S 0.04274(12) 0.22785(7) 0.34132(7) 0.0442(3) Uani 1 1 d . . . . . S003 S 0.51978(12) 0.19624(7) 0.17538(8) 0.0454(3) Uani 1 1 d . . . . . S004 S 0.42472(12) 0.28231(8) 0.52924(8) 0.0500(3) Uani 1 1 d . . . . . O005 O -0.3077(2) 0.76410(17) 0.22147(17) 0.0333(6) Uani 1 1 d . . . . . O006 O 0.1387(2) 0.87673(17) 0.23158(18) 0.0364(6) Uani 1 1 d . . . . . N007 N -0.0726(3) 0.75012(19) 0.25263(19) 0.0260(6) Uani 1 1 d . . . . . H007 H -0.007873 0.786465 0.253152 0.031 Uiso 1 1 calc R . . . . N008 N 0.3602(3) 0.3576(2) 0.06902(18) 0.0279(6) Uani 1 1 d . . . . . N009 N 0.3879(3) 0.77632(19) 0.20424(19) 0.0275(6) Uani 1 1 d . . . . . H009 H 0.482449 0.768997 0.211852 0.033 Uiso 1 1 calc R . . . . N00A N 0.2439(3) 0.2711(2) 0.41831(19) 0.0315(7) Uani 1 1 d . . . . . C00B C 0.0706(3) 0.6011(2) 0.3504(2) 0.0233(7) Uani 1 1 d . . . . . C00C C 0.4085(3) 0.5113(2) 0.1530(2) 0.0231(7) Uani 1 1 d . . . . . C00D C 0.3622(3) 0.6970(2) 0.1652(2) 0.0247(7) Uani 1 1 d . . . . . C00E C 0.0783(3) 0.4215(2) 0.3350(2) 0.0244(7) Uani 1 1 d . . . . . C00F C 0.3146(3) 0.5424(2) 0.0828(2) 0.0255(7) Uani 1 1 d . . . . . C00G C 0.4339(3) 0.5896(2) 0.1950(2) 0.0249(7) Uani 1 1 d . . . . . C00H C -0.0263(3) 0.6411(2) 0.2811(2) 0.0249(7) Uani 1 1 d . . . . . C00I C 0.4771(3) 0.4037(2) 0.1810(2) 0.0256(7) Uani 1 1 d . . . . . C00J C 0.2285(3) 0.4481(2) 0.4403(2) 0.0266(7) Uani 1 1 d . . . . . C00K C 0.1266(3) 0.4901(2) 0.3749(2) 0.0233(7) Uani 1 1 d . . . . . C00L C 0.2760(4) 0.8630(2) 0.2307(3) 0.0314(8) Uani 1 1 d . . . . . C00M C 0.5285(3) 0.5566(2) 0.2645(2) 0.0262(7) Uani 1 1 d . . . . . H00M H 0.545654 0.607340 0.293684 0.031 Uiso 1 1 calc R . . . . C00N C 0.1136(3) 0.6664(3) 0.3970(2) 0.0281(7) Uani 1 1 d . . . . . H00N H 0.074935 0.740688 0.383403 0.034 Uiso 1 1 calc R . . . . C00O C -0.2077(4) 0.8056(2) 0.2242(2) 0.0278(7) Uani 1 1 d . . . . . C00P C -0.0677(4) 0.5726(2) 0.2410(2) 0.0294(7) Uani 1 1 d . . . . . H00P H -0.131338 0.599551 0.194296 0.035 Uiso 1 1 calc R . . . . C00Q C 0.5707(4) 0.3753(3) 0.2492(2) 0.0296(7) Uani 1 1 d . . . . . H00Q H 0.618038 0.303024 0.268126 0.035 Uiso 1 1 calc R . . . . C00R C 0.2101(4) 0.6242(3) 0.4614(2) 0.0301(8) Uani 1 1 d . . . . . H00R H 0.237495 0.669466 0.491830 0.036 Uiso 1 1 calc R . . . . C00S C 0.2900(3) 0.4627(3) 0.0385(2) 0.0283(7) Uani 1 1 d . . . . . C00T C 0.1266(4) 0.3084(3) 0.3655(2) 0.0295(8) Uani 1 1 d . . . . . C00U C 0.2481(4) 0.6478(3) 0.0563(2) 0.0303(8) Uani 1 1 d . . . . . H00U H 0.184657 0.668454 0.009529 0.036 Uiso 1 1 calc R . . . . C00V C 0.2718(4) 0.7242(3) 0.0965(2) 0.0301(8) Uani 1 1 d . . . . . H00V H 0.225184 0.796302 0.076504 0.036 Uiso 1 1 calc R . . . . C00W C -0.0168(4) 0.4646(3) 0.2683(2) 0.0290(7) Uani 1 1 d . . . . . H00W H -0.048063 0.418886 0.240587 0.035 Uiso 1 1 calc R . . . . C00X C 0.5959(4) 0.4515(3) 0.2902(2) 0.0306(8) Uani 1 1 d . . . . . H00X H 0.660424 0.430449 0.336357 0.037 Uiso 1 1 calc R . . . . C00Y C 0.2683(4) 0.5161(3) 0.4825(2) 0.0320(8) Uani 1 1 d . . . . . H00Y H 0.336417 0.488314 0.526548 0.038 Uiso 1 1 calc R . . . . C00Z C 0.2945(4) 0.3341(3) 0.4599(2) 0.0336(8) Uani 1 1 d . . . . . C010 C -0.2261(4) 0.9222(2) 0.1969(3) 0.0347(8) Uani 1 1 d . . . . . H01M H -0.256368 0.946318 0.134012 0.052 Uiso 1 1 calc GR . . . . H01N H -0.127372 0.938034 0.192992 0.052 Uiso 1 1 calc GR . . . . H01O H -0.306639 0.958267 0.245818 0.052 Uiso 1 1 calc GR . . . . C011 C 0.3306(4) 0.2772(3) 0.0264(2) 0.0330(8) Uani 1 1 d . . . . . H01A H 0.420490 0.214634 0.025393 0.040 Uiso 1 1 calc R . . . . H01B H 0.319018 0.306058 -0.041090 0.040 Uiso 1 1 calc R . . . . C012 C 0.4497(4) 0.3226(3) 0.1400(2) 0.0307(8) Uani 1 1 d . . . . . C013 C 0.1835(4) 0.2444(3) 0.0843(3) 0.0373(9) Uani 1 1 d . . . . . H01C H 0.200240 0.207916 0.149407 0.045 Uiso 1 1 calc R . . . . H01D H 0.096573 0.308208 0.092213 0.045 Uiso 1 1 calc R . . . . C014 C 0.3349(4) 0.9424(3) 0.2589(3) 0.0477(10) Uani 1 1 d . . . . . H01E H 0.386003 0.981883 0.200714 0.072 Uiso 1 1 calc GR . . . . H01F H 0.409475 0.905887 0.300640 0.072 Uiso 1 1 calc GR . . . . H01G H 0.247439 0.991170 0.293780 0.072 Uiso 1 1 calc GR . . . . C015 C 0.1399(5) 0.1724(3) 0.0355(3) 0.0471(10) Uani 1 1 d . . . . . H01H H 0.230353 0.111756 0.022485 0.056 Uiso 1 1 calc R . . . . H01I H 0.114891 0.211124 -0.027320 0.056 Uiso 1 1 calc R . . . . C016 C 0.3112(4) 0.1562(3) 0.4345(3) 0.0433(9) Uani 1 1 d . . . . . H01P H 0.421520 0.142110 0.438224 0.052 Uiso 1 1 calc R . . . . H01Q H 0.308205 0.126932 0.378505 0.052 Uiso 1 1 calc R . . . . C017 C 0.2272(5) 0.1006(3) 0.5254(3) 0.0526(11) Uani 1 1 d . . . . . H01R H 0.113664 0.128762 0.530455 0.063 Uiso 1 1 calc R . . . . H01S H 0.254251 0.114212 0.582291 0.063 Uiso 1 1 calc R . . . . C018 C 0.0021(5) 0.1317(3) 0.0958(3) 0.0598(12) Uani 1 1 d . . . . . H01J H -0.025281 0.089397 0.059261 0.090 Uiso 1 1 calc GR . . . . H01K H -0.086750 0.191330 0.111229 0.090 Uiso 1 1 calc GR . . . . H01L H 0.029241 0.088052 0.155731 0.090 Uiso 1 1 calc GR . . . . C019 C 0.2160(6) -0.0787(4) 0.6135(3) 0.0670(13) Uani 1 1 d . . . . . H01T H 0.228086 -0.150139 0.602547 0.100 Uiso 1 1 calc GR . . . . H01U H 0.106054 -0.046589 0.637657 0.100 Uiso 1 1 calc GR . . . . H01V H 0.276286 -0.081925 0.661231 0.100 Uiso 1 1 calc GR . . . . C01A C 0.2708(6) -0.0172(3) 0.5252(4) 0.0780(16) Uani 1 1 d . . . . . H01W H 0.229724 -0.030028 0.473540 0.094 Uiso 1 1 calc R . . . . H01X H 0.385493 -0.041948 0.508684 0.094 Uiso 1 1 calc R . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S001 0.0364(5) 0.0503(6) 0.0392(5) -0.0120(4) -0.0111(4) -0.0147(4) S002 0.0557(6) 0.0325(5) 0.0479(6) -0.0123(4) -0.0104(5) -0.0120(4) S003 0.0526(6) 0.0287(5) 0.0576(6) -0.0078(4) -0.0171(5) -0.0091(4) S004 0.0493(6) 0.0416(6) 0.0602(7) -0.0021(5) -0.0310(5) -0.0008(5) O005 0.0225(12) 0.0335(13) 0.0490(15) -0.0037(11) -0.0151(10) -0.0104(10) O006 0.0196(12) 0.0247(12) 0.0675(17) -0.0142(11) -0.0109(11) -0.0030(9) N007 0.0191(13) 0.0230(14) 0.0398(16) -0.0048(12) -0.0101(11) -0.0080(11) N008 0.0264(14) 0.0332(16) 0.0292(15) -0.0104(12) -0.0026(12) -0.0136(12) N009 0.0154(13) 0.0237(14) 0.0451(17) -0.0072(12) -0.0086(12) -0.0042(11) N00A 0.0296(15) 0.0268(15) 0.0353(16) -0.0084(12) -0.0073(13) 0.0001(12) C00B 0.0157(15) 0.0263(17) 0.0277(17) -0.0080(13) -0.0025(13) -0.0039(13) C00C 0.0154(15) 0.0260(17) 0.0282(17) -0.0054(13) 0.0003(13) -0.0092(13) C00D 0.0172(15) 0.0201(16) 0.0352(18) -0.0055(14) -0.0002(13) -0.0063(12) C00E 0.0200(15) 0.0269(17) 0.0261(17) -0.0086(13) 0.0000(13) -0.0065(13) C00F 0.0183(15) 0.0307(18) 0.0291(17) -0.0073(14) -0.0020(13) -0.0094(13) C00G 0.0160(15) 0.0280(17) 0.0302(17) -0.0049(14) -0.0005(13) -0.0083(13) C00H 0.0176(15) 0.0275(17) 0.0318(18) -0.0070(14) -0.0056(13) -0.0067(13) C00I 0.0229(16) 0.0247(17) 0.0270(17) -0.0050(14) -0.0008(13) -0.0061(13) C00J 0.0198(16) 0.0323(18) 0.0255(17) -0.0068(14) -0.0016(13) -0.0044(13) C00K 0.0154(15) 0.0305(17) 0.0238(16) -0.0082(13) -0.0013(12) -0.0049(13) C00L 0.0262(18) 0.0216(17) 0.048(2) -0.0076(15) -0.0069(15) -0.0073(14) C00M 0.0245(16) 0.0287(18) 0.0283(17) -0.0075(14) -0.0045(14) -0.0097(14) C00N 0.0210(16) 0.0313(18) 0.0334(18) -0.0140(15) -0.0016(14) -0.0058(14) C00O 0.0247(17) 0.0307(18) 0.0293(18) -0.0048(14) -0.0061(14) -0.0085(14) C00P 0.0254(17) 0.0297(18) 0.0381(19) -0.0062(15) -0.0138(15) -0.0074(14) C00Q 0.0289(18) 0.0261(18) 0.0331(19) -0.0027(14) -0.0077(14) -0.0065(14) C00R 0.0249(17) 0.036(2) 0.0337(19) -0.0138(15) -0.0074(14) -0.0070(14) C00S 0.0209(16) 0.0346(19) 0.0298(18) -0.0092(15) 0.0029(14) -0.0118(14) C00T 0.0278(17) 0.0330(19) 0.0237(17) -0.0092(14) 0.0015(14) -0.0041(14) C00U 0.0231(16) 0.0335(19) 0.0348(19) -0.0039(15) -0.0084(14) -0.0070(14) C00V 0.0229(17) 0.0281(18) 0.040(2) -0.0041(15) -0.0088(15) -0.0061(14) C00W 0.0246(17) 0.0307(18) 0.0358(19) -0.0112(15) -0.0047(14) -0.0098(14) C00X 0.0280(17) 0.0330(19) 0.0319(18) -0.0036(15) -0.0115(14) -0.0062(15) C00Y 0.0245(17) 0.043(2) 0.0291(18) -0.0083(15) -0.0090(14) -0.0055(15) C00Z 0.0273(18) 0.037(2) 0.0328(19) -0.0071(16) -0.0029(15) -0.0042(15) C010 0.0325(19) 0.0260(18) 0.047(2) -0.0041(16) -0.0151(16) -0.0055(15) C011 0.039(2) 0.0320(19) 0.0333(19) -0.0135(15) -0.0002(15) -0.0177(16) C012 0.0269(18) 0.0302(18) 0.0349(19) -0.0114(15) 0.0032(15) -0.0104(14) C013 0.041(2) 0.043(2) 0.035(2) -0.0077(16) -0.0039(16) -0.0235(17) C014 0.035(2) 0.034(2) 0.085(3) -0.029(2) -0.017(2) -0.0069(17) C015 0.058(3) 0.051(2) 0.046(2) -0.0066(19) -0.0127(19) -0.034(2) C016 0.044(2) 0.030(2) 0.050(2) -0.0114(17) -0.0142(18) 0.0067(17) C017 0.078(3) 0.029(2) 0.050(2) -0.0056(18) -0.020(2) -0.006(2) C018 0.068(3) 0.063(3) 0.063(3) 0.011(2) -0.026(2) -0.043(2) C019 0.080(3) 0.056(3) 0.064(3) -0.006(2) -0.014(3) -0.020(3) C01A 0.062(3) 0.045(3) 0.095(4) 0.015(3) -0.006(3) 0.005(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C00H N007 H007 116.7 . . ? C00O N007 H007 116.7 . . ? C00O N007 C00H 126.5(3) . . ? C00S N008 C011 117.3(3) . . ? C00S N008 C012 124.7(3) . . ? C012 N008 C011 117.9(3) . . ? C00D N009 H009 117.8 . . ? C00L N009 H009 117.8 . . ? C00L N009 C00D 124.4(3) . . ? C00T N00A C016 117.0(3) . . ? C00Z N00A C00T 124.1(3) . . ? C00Z N00A C016 118.8(3) . . ? C00K C00B C00H 118.8(3) . . ? C00N C00B C00H 123.2(3) . . ? C00N C00B C00K 118.0(3) . . ? C00F C00C C00G 119.7(3) . . ? C00I C00C C00F 120.0(3) . . ? C00I C00C C00G 120.2(3) . . ? N009 C00D C00G 119.6(3) . . ? C00V C00D N009 120.3(3) . . ? C00V C00D C00G 120.1(3) . . ? C00K C00E C00T 119.8(3) . . ? C00W C00E C00K 118.7(3) . . ? C00W C00E C00T 121.4(3) . . ? C00C C00F C00S 120.0(3) . . ? C00U C00F C00C 119.5(3) . . ? C00U C00F C00S 120.5(3) . . ? C00D C00G C00C 118.5(3) . . ? C00M C00G C00C 118.7(3) . . ? C00M C00G C00D 122.9(3) . . ? N007 C00H C00B 118.6(3) . . ? C00P C00H N007 121.4(3) . . ? C00P C00H C00B 120.0(3) . . ? C00C C00I C012 120.8(3) . . ? C00Q C00I C00C 118.9(3) . . ? C00Q C00I C012 120.3(3) . . ? C00K C00J C00Z 119.8(3) . . ? C00Y C00J C00K 119.2(3) . . ? C00Y C00J C00Z 121.0(3) . . ? C00E C00K C00B 120.0(3) . . ? C00J C00K C00B 120.0(3) . . ? C00J C00K C00E 120.0(3) . . ? O006 C00L N009 123.5(3) . . ? O006 C00L C014 121.9(3) . . ? N009 C00L C014 114.6(3) . . ? C00G C00M H00M 119.8 . . ? C00X C00M C00G 120.4(3) . . ? C00X C00M H00M 119.8 . . ? C00B C00N H00N 119.5 . . ? C00R C00N C00B 121.0(3) . . ? C00R C00N H00N 119.5 . . ? O005 C00O N007 122.8(3) . . ? O005 C00O C010 122.2(3) . . ? N007 C00O C010 115.0(3) . . ? C00H C00P H00P 119.8 . . ? C00H C00P C00W 120.4(3) . . ? C00W C00P H00P 119.8 . . ? C00I C00Q H00Q 119.5 . . ? C00I C00Q C00X 121.0(3) . . ? C00X C00Q H00Q 119.5 . . ? C00N C00R H00R 119.7 . . ? C00N C00R C00Y 120.7(3) . . ? C00Y C00R H00R 119.7 . . ? N008 C00S S001 121.3(2) . . ? N008 C00S C00F 117.5(3) . . ? C00F C00S S001 121.2(2) . . ? N00A C00T S002 121.3(2) . . ? N00A C00T C00E 117.3(3) . . ? C00E C00T S002 121.4(3) . . ? C00F C00U H00U 119.4 . . ? C00F C00U C00V 121.3(3) . . ? C00V C00U H00U 119.4 . . ? C00D C00V C00U 121.0(3) . . ? C00D C00V H00V 119.5 . . ? C00U C00V H00V 119.5 . . ? C00E C00W C00P 121.9(3) . . ? C00E C00W H00W 119.0 . . ? C00P C00W H00W 119.0 . . ? C00M C00X C00Q 120.8(3) . . ? C00M C00X H00X 119.6 . . ? C00Q C00X H00X 119.6 . . ? C00J C00Y C00R 121.0(3) . . ? C00J C00Y H00Y 119.5 . . ? C00R C00Y H00Y 119.5 . . ? N00A C00Z S004 121.1(3) . . ? N00A C00Z C00J 117.5(3) . . ? C00J C00Z S004 121.4(3) . . ? C00O C010 H01M 109.5 . . ? C00O C010 H01N 109.5 . . ? C00O C010 H01O 109.5 . . ? H01M C010 H01N 109.5 . . ? H01M C010 H01O 109.5 . . ? H01N C010 H01O 109.5 . . ? N008 C011 H01A 109.4 . . ? N008 C011 H01B 109.4 . . ? N008 C011 C013 111.1(3) . . ? H01A C011 H01B 108.0 . . ? C013 C011 H01A 109.4 . . ? C013 C011 H01B 109.4 . . ? N008 C012 S003 121.1(2) . . ? N008 C012 C00I 116.8(3) . . ? C00I C012 S003 122.1(3) . . ? C011 C013 H01C 109.2 . . ? C011 C013 H01D 109.2 . . ? H01C C013 H01D 107.9 . . ? C015 C013 C011 112.1(3) . . ? C015 C013 H01C 109.2 . . ? C015 C013 H01D 109.2 . . ? C00L C014 H01E 109.5 . . ? C00L C014 H01F 109.5 . . ? C00L C014 H01G 109.5 . . ? H01E C014 H01F 109.5 . . ? H01E C014 H01G 109.5 . . ? H01F C014 H01G 109.5 . . ? C013 C015 H01H 109.0 . . ? C013 C015 H01I 109.0 . . ? C013 C015 C018 112.9(3) . . ? H01H C015 H01I 107.8 . . ? C018 C015 H01H 109.0 . . ? C018 C015 H01I 109.0 . . ? N00A C016 H01P 109.0 . . ? N00A C016 H01Q 109.0 . . ? N00A C016 C017 113.1(3) . . ? H01P C016 H01Q 107.8 . . ? C017 C016 H01P 109.0 . . ? C017 C016 H01Q 109.0 . . ? C016 C017 H01R 109.4 . . ? C016 C017 H01S 109.4 . . ? C016 C017 C01A 111.0(3) . . ? H01R C017 H01S 108.0 . . ? C01A C017 H01R 109.4 . . ? C01A C017 H01S 109.4 . . ? C015 C018 H01J 109.5 . . ? C015 C018 H01K 109.5 . . ? C015 C018 H01L 109.5 . . ? H01J C018 H01K 109.5 . . ? H01J C018 H01L 109.5 . . ? H01K C018 H01L 109.5 . . ? H01T C019 H01U 109.5 . . ? H01T C019 H01V 109.5 . . ? H01U C019 H01V 109.5 . . ? C01A C019 H01T 109.5 . . ? C01A C019 H01U 109.5 . . ? C01A C019 H01V 109.5 . . ? C017 C01A H01W 108.4 . . ? C017 C01A H01X 108.4 . . ? C019 C01A C017 115.4(4) . . ? C019 C01A H01W 108.4 . . ? C019 C01A H01X 108.4 . . ? H01W C01A H01X 107.5 . . ? 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 S001 C00S 1.644(3) . ? S002 C00T 1.647(3) . ? S003 C012 1.644(3) . ? S004 C00Z 1.657(4) . ? O005 C00O 1.225(4) . ? O006 C00L 1.219(4) . ? N007 H007 0.8800 . ? N007 C00H 1.399(4) . ? N007 C00O 1.359(4) . ? N008 C00S 1.393(4) . ? N008 C011 1.482(4) . ? N008 C012 1.397(4) . ? N009 H009 0.8800 . ? N009 C00D 1.419(4) . ? N009 C00L 1.362(4) . ? N00A C00T 1.392(4) . ? N00A C00Z 1.385(4) . ? N00A C016 1.475(4) . ? C00B C00H 1.425(4) . ? C00B C00K 1.423(4) . ? C00B C00N 1.417(4) . ? C00C C00F 1.417(4) . ? C00C C00G 1.432(4) . ? C00C C00I 1.410(4) . ? C00D C00G 1.420(4) . ? C00D C00V 1.380(5) . ? C00E C00K 1.418(4) . ? C00E C00T 1.453(4) . ? C00E C00W 1.386(4) . ? C00F C00S 1.468(4) . ? C00F C00U 1.377(4) . ? C00G C00M 1.413(4) . ? C00H C00P 1.380(4) . ? C00I C00Q 1.394(4) . ? C00I C012 1.466(4) . ? C00J C00K 1.416(4) . ? C00J C00Y 1.386(5) . ? C00J C00Z 1.465(5) . ? C00L C014 1.505(5) . ? C00M H00M 0.9500 . ? C00M C00X 1.373(4) . ? C00N H00N 0.9500 . ? C00N C00R 1.369(5) . ? C00O C010 1.500(4) . ? C00P H00P 0.9500 . ? C00P C00W 1.388(4) . ? C00Q H00Q 0.9500 . ? C00Q C00X 1.398(4) . ? C00R H00R 0.9500 . ? C00R C00Y 1.386(5) . ? C00U H00U 0.9500 . ? C00U C00V 1.386(4) . ? C00V H00V 0.9500 . ? C00W H00W 0.9500 . ? C00X H00X 0.9500 . ? C00Y H00Y 0.9500 . ? C010 H01M 0.9800 . ? C010 H01N 0.9800 . ? C010 H01O 0.9800 . ? C011 H01A 0.9900 . ? C011 H01B 0.9900 . ? C011 C013 1.529(5) . ? C013 H01C 0.9900 . ? C013 H01D 0.9900 . ? C013 C015 1.516(5) . ? C014 H01E 0.9800 . ? C014 H01F 0.9800 . ? C014 H01G 0.9800 . ? C015 H01H 0.9900 . ? C015 H01I 0.9900 . ? C015 C018 1.518(5) . ? C016 H01P 0.9900 . ? C016 H01Q 0.9900 . ? C016 C017 1.508(5) . ? C017 H01R 0.9900 . ? C017 H01S 0.9900 . ? C017 C01A 1.518(6) . ? C018 H01J 0.9800 . ? C018 H01K 0.9800 . ? C018 H01L 0.9800 . ? C019 H01T 0.9800 . ? C019 H01U 0.9800 . ? C019 H01V 0.9800 . ? C019 C01A 1.423(6) . ? C01A H01W 0.9900 . ? C01A H01X 0.9900 . ?