#------------------------------------------------------------------------------ #$Date: 2023-12-01 19:20:38 +0200 (Fri, 01 Dec 2023) $ #$Revision: 287940 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225269.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_7225269 loop_ _publ_author_name 'Payne, Abby-Jo' 'Hendsbee, Arthur D.' 'McAfee, Seth M.' 'Paul, Devproshad K.' 'Karan, Kunal' 'Welch, Gregory C.' _publ_section_exptl_refinement ; The H atoms were placed in geometrically idealized positions with C-H distances of 0.93\%A (aromatic),0.97\%A (idealized CH~2~) and 0.96\%A (idealized CH~3~) and were constrained to ride on the parent C atom with Uiso(H) = 1.2Ueq(C) for the aromatic, CH~2~ and C-H protons and Uiso(H) = 1.5Ueq(C) for the idealized CH~3~ protons. ; _publ_section_title ; Synthesis and structure-property relationships of phthalimide and naphthalimide based organic \p-conjugated small molecules. ; _journal_issue 21 _journal_name_full 'Physical chemistry chemical physics : PCCP' _journal_page_first 14709 _journal_page_last 14719 _journal_paper_doi 10.1039/c6cp01596d _journal_volume 18 _journal_year 2016 _chemical_formula_moiety 'C48 H48 N2 O4 S2' _chemical_formula_sum 'C48 H48 N2 O4 S2' _chemical_formula_weight 781.02 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2015-11-06 deposited with the CCDC. 2016-05-17 downloaded from the CCDC. ; _cell_angle_alpha 94.98(2) _cell_angle_beta 93.06(2) _cell_angle_gamma 116.609(15) _cell_formula_units_Z 1 _cell_length_a 8.870(13) _cell_length_b 9.773(14) _cell_length_c 13.13(3) _cell_measurement_temperature 125(2) _cell_volume 1008(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'LinXTL v. 5.4.5' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 125(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.917 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.2034 _diffrn_reflns_av_unetI/netI 0.3251 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.917 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 11387 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.917 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.435 _diffrn_reflns_theta_min 2.349 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.3515 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 414 _exptl_crystal_size_max 0.299 _exptl_crystal_size_mid 0.282 _exptl_crystal_size_min 0.190 _refine_diff_density_max 0.757 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.114 _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 255 _refine_ls_number_reflns 4660 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.082 _refine_ls_R_factor_all 0.2914 _refine_ls_R_factor_gt 0.1161 _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^)+(0.0100P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2137 _refine_ls_wR_factor_ref 0.2638 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1483 _reflns_number_total 4660 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6cp01596d2.cif _cod_data_source_block 06_02_2014_ADH2nap2_0ma _cod_depositor_comments 'Adding full bibliography for 7225267--7225270.cif.' _cod_database_code 7225269 _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_min 0.3515 _shelx_estimated_absorpt_t_max 0.7457 _shelxl_version_number 2013-4 _shelx_res_file ; TITL 06_02_2014_ADH2nap2_0ma in New: P-1 CELL 0.71073 8.8700 9.7730 13.1300 94.980 93.060 116.609 ZERR 1 0.0130 0.0140 0.0300 0.020 0.020 0.015 LATT 1 SFAC C 2.31000 20.84392 1.02000 10.20751 1.58860 0.56870 0.86500 = 51.65125 0.21560 0.00330 0.00160 11.500 0.68000 12.01000 SFAC H 0.49300 10.51091 0.32291 26.12573 0.14019 3.14236 0.04081 = 57.79977 0.00304 0.00000 0.00000 0.624 0.35000 1.00800 SFAC N 12.21261 0.00570 3.13220 9.89331 2.01250 28.99754 1.16630 = 0.58260 -11.52901 0.00610 0.00330 19.600 0.68000 14.01000 SFAC O 3.04850 13.27711 2.28680 5.70111 1.54630 0.32390 0.86700 = 32.90894 0.25080 0.01060 0.00600 32.500 0.68000 16.00000 SFAC S 6.90531 1.46790 5.20341 22.21512 1.43790 0.25360 1.58630 = 56.17207 0.86690 0.12460 0.12340 532.000 1.04000 32.07000 UNIT 48 48 2 4 2 TEMP -148 L.S. 5 FMAP 2 PLAN 20 ACTA CONF BOND $H WGHT 0.010000 EXTI 0.012160 FVAR 0.19857 S1 5 -0.279564 -0.409490 0.116026 11.00000 0.01202 0.04545 = 0.05461 0.00200 0.00145 0.01061 O1 4 0.581880 -0.190469 0.353095 11.00000 0.02399 0.07615 = 0.06529 0.02575 0.00750 0.02553 O2 4 0.793728 0.242689 0.192774 11.00000 0.01677 0.04365 = 0.07014 0.00120 0.00394 0.01168 N1 3 0.685435 0.025785 0.274213 11.00000 0.01405 0.04342 = 0.05567 0.00173 0.00037 0.01436 C1 1 -0.405487 -0.466260 0.000104 11.00000 0.02017 0.03613 = 0.03037 -0.00001 -0.00266 0.00524 C2 1 -0.312321 -0.433223 -0.080210 11.00000 0.01889 0.05071 = 0.03145 0.00525 0.00116 0.01283 AFIX 43 H2 2 -0.359940 -0.455278 -0.149788 11.00000 -1.20000 AFIX 0 C3 1 -0.133511 -0.361179 -0.049483 11.00000 0.01384 0.05366 = 0.05300 -0.00195 0.00967 0.01901 AFIX 43 H3 2 -0.050118 -0.331936 -0.096643 11.00000 -1.20000 AFIX 0 C4 1 -0.096092 -0.339257 0.053556 11.00000 0.00998 0.04419 = 0.03585 0.00355 -0.00111 0.01227 C5 1 0.071039 -0.277943 0.116507 11.00000 0.01879 0.04277 = 0.05751 -0.00611 0.00163 0.02168 C6 1 0.093653 -0.355440 0.193541 11.00000 0.01982 0.05156 = 0.06500 0.00807 0.00749 0.02078 AFIX 43 H6 2 0.000542 -0.446326 0.208787 11.00000 -1.20000 AFIX 0 C7 1 0.254570 -0.301581 0.250881 11.00000 0.02101 0.04881 = 0.05342 -0.00104 -0.00009 0.02091 AFIX 43 H7 2 0.269299 -0.359371 0.301647 11.00000 -1.20000 AFIX 0 C8 1 0.388880 -0.166411 0.233268 11.00000 0.02101 0.04053 = 0.04813 0.00069 0.00843 0.01703 C9 1 0.369371 -0.078159 0.158728 11.00000 0.01883 0.03184 = 0.05124 0.00043 0.00578 0.01465 C10 1 0.206151 -0.132641 0.099339 11.00000 0.01422 0.03977 = 0.04761 0.00267 0.00375 0.01199 C11 1 0.192576 -0.038600 0.027330 11.00000 0.02198 0.04086 = 0.04927 0.00559 0.00503 0.01725 AFIX 43 H11 2 0.087043 -0.071694 -0.012586 11.00000 -1.20000 AFIX 0 C12 1 0.324762 0.097746 0.012768 11.00000 0.02296 0.04358 = 0.04806 -0.00244 -0.00498 0.02408 AFIX 43 H12 2 0.310504 0.157138 -0.036989 11.00000 -1.20000 AFIX 0 C13 1 0.485080 0.151733 0.072258 11.00000 0.01984 0.03207 = 0.05739 0.00940 0.00813 0.01014 AFIX 43 H13 2 0.577544 0.246863 0.062466 11.00000 -1.20000 AFIX 0 C14 1 0.503482 0.064188 0.143691 11.00000 0.01860 0.03484 = 0.03883 0.00073 0.00182 0.01089 C15 1 0.673551 0.121312 0.204612 11.00000 0.02630 0.04908 = 0.03969 0.00146 0.00093 0.01923 C16 1 0.559236 -0.114161 0.292316 11.00000 0.02184 0.04687 = 0.04465 0.01022 0.00642 0.01492 C17 1 0.855598 0.075668 0.333129 11.00000 0.01872 0.06386 = 0.04857 -0.00566 -0.00290 0.02374 AFIX 23 H17A 2 0.839792 0.050695 0.404486 11.00000 -1.20000 H17B 2 0.923763 0.188736 0.335910 11.00000 -1.20000 AFIX 0 C18 1 0.950875 -0.005637 0.282014 11.00000 0.01803 0.04449 = 0.05610 -0.00826 -0.00579 0.01392 AFIX 23 H18A 2 0.967361 0.020072 0.210847 11.00000 -1.20000 H18B 2 0.882034 -0.118711 0.278623 11.00000 -1.20000 AFIX 0 C19 1 1.124433 0.043552 0.342277 11.00000 0.02030 0.04868 = 0.04215 -0.00060 -0.00083 0.01646 AFIX 23 H19A 2 1.110322 0.043909 0.416572 11.00000 -1.20000 H19B 2 1.164121 -0.034027 0.322638 11.00000 -1.20000 AFIX 0 C20 1 1.260430 0.202399 0.324306 11.00000 0.02387 0.06046 = 0.05282 0.00365 0.00523 0.02413 AFIX 23 H20A 2 1.219560 0.279804 0.341649 11.00000 -1.20000 H20B 2 1.278260 0.201194 0.250508 11.00000 -1.20000 AFIX 0 C21 1 1.431006 0.251433 0.388438 11.00000 0.02392 0.06838 = 0.04017 0.01061 0.00414 0.03113 AFIX 23 H21A 2 1.411727 0.249516 0.461988 11.00000 -1.20000 H21B 2 1.472049 0.174480 0.369942 11.00000 -1.20000 AFIX 0 C22 1 1.566795 0.407910 0.374827 11.00000 0.01449 0.06374 = 0.06235 0.00348 0.00098 0.01190 AFIX 23 H22A 2 1.524853 0.484621 0.391863 11.00000 -1.20000 H22B 2 1.587925 0.409143 0.301554 11.00000 -1.20000 AFIX 0 C23 1 1.735509 0.457918 0.440546 11.00000 0.02104 0.07676 = 0.05796 -0.00672 -0.00200 0.02643 AFIX 23 H23A 2 1.713592 0.450279 0.513495 11.00000 -1.20000 H23B 2 1.781770 0.385474 0.420201 11.00000 -1.20000 AFIX 0 C24 1 1.869033 0.622269 0.430923 11.00000 0.02810 0.06576 = 0.07092 -0.00360 0.00460 0.01887 AFIX 137 H24A 2 1.893286 0.630628 0.359146 11.00000 -1.50000 H24B 2 1.973183 0.645984 0.474282 11.00000 -1.50000 H24C 2 1.826067 0.695358 0.453184 11.00000 -1.50000 AFIX 0 HKLF 4 REM 06_02_2014_ADH2nap2_0ma in New: P-1 REM R1 = 0.1161 for 1483 Fo > 4sig(Fo) and 0.2914 for all 4660 data REM 255 parameters refined using 0 restraints END WGHT 0.1394 0.0000 REM Highest difference peak 0.757, deepest hole -0.552, 1-sigma level 0.114 Q1 1 -0.3277 -0.5186 0.0579 11.00000 0.05 0.76 Q2 1 -0.2381 -0.3104 0.1860 11.00000 0.05 0.75 Q3 1 -0.2947 -0.4276 0.0319 11.00000 0.05 0.67 Q4 1 -0.2370 -0.2870 0.1351 11.00000 0.05 0.62 Q5 1 0.6466 0.0185 0.1666 11.00000 0.05 0.47 Q6 1 0.3945 -0.0578 0.2416 11.00000 0.05 0.46 Q7 1 0.6190 -0.0530 0.3680 11.00000 0.05 0.42 Q8 1 0.4585 0.0264 0.0662 11.00000 0.05 0.41 Q9 1 0.2289 -0.0288 0.1100 11.00000 0.05 0.40 Q10 1 0.6369 -0.0852 0.4249 11.00000 0.05 0.40 Q11 1 0.0609 -0.3827 0.1120 11.00000 0.05 0.39 Q12 1 -0.3755 -0.3442 0.0104 11.00000 0.05 0.39 Q13 1 0.5256 0.2330 0.1402 11.00000 0.05 0.39 Q14 1 0.1625 -0.1741 0.0070 11.00000 0.05 0.39 Q15 1 0.6983 0.1273 0.2739 11.00000 0.05 0.37 Q16 1 -0.0622 -0.2203 0.0544 11.00000 0.05 0.37 Q17 1 0.6264 -0.0588 0.2173 11.00000 0.05 0.37 Q18 1 0.7571 0.1655 0.1347 11.00000 0.05 0.37 Q19 1 0.3564 -0.1798 0.1657 11.00000 0.05 0.36 Q20 1 0.5677 0.3157 0.0447 11.00000 0.05 0.36 ; _shelx_res_checksum 6910 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 S1 S -0.2796(2) -0.4095(2) 0.11603(15) 0.0386(6) Uani 1 1 d . . O1 O 0.5819(6) -0.1905(6) 0.3531(4) 0.0529(15) Uani 1 1 d . . O2 O 0.7937(6) 0.2427(5) 0.1928(4) 0.0447(14) Uani 1 1 d . . N1 N 0.6854(6) 0.0258(6) 0.2742(4) 0.0376(16) Uani 1 1 d . . C1 C -0.4055(8) -0.4663(7) 0.0001(5) 0.0322(18) Uani 1 1 d . . C2 C -0.3123(8) -0.4332(7) -0.0802(5) 0.0349(18) Uani 1 1 d . . H2 H -0.3599 -0.4553 -0.1498 0.042 Uiso 1 1 calc R U C3 C -0.1335(8) -0.3612(8) -0.0495(6) 0.039(2) Uani 1 1 d . . H3 H -0.0501 -0.3319 -0.0966 0.047 Uiso 1 1 calc R U C4 C -0.0961(7) -0.3393(7) 0.0536(5) 0.0303(17) Uani 1 1 d . . C5 C 0.0710(8) -0.2779(8) 0.1165(6) 0.0377(19) Uani 1 1 d . . C6 C 0.0937(8) -0.3554(8) 0.1935(6) 0.044(2) Uani 1 1 d . . H6 H 0.0005 -0.4463 0.2088 0.052 Uiso 1 1 calc R U C7 C 0.2546(8) -0.3016(8) 0.2509(5) 0.0398(19) Uani 1 1 d . . H7 H 0.2693 -0.3594 0.3016 0.048 Uiso 1 1 calc R U C8 C 0.3889(8) -0.1664(8) 0.2333(5) 0.0355(18) Uani 1 1 d . . C9 C 0.3694(8) -0.0782(8) 0.1587(5) 0.0330(18) Uani 1 1 d . . C10 C 0.2062(8) -0.1326(8) 0.0993(5) 0.0341(18) Uani 1 1 d . . C11 C 0.1926(8) -0.0386(8) 0.0273(5) 0.0362(18) Uani 1 1 d . . H11 H 0.0870 -0.0717 -0.0126 0.043 Uiso 1 1 calc R U C12 C 0.3248(8) 0.0977(8) 0.0128(5) 0.0357(18) Uani 1 1 d . . H12 H 0.3105 0.1571 -0.0370 0.043 Uiso 1 1 calc R U C13 C 0.4851(8) 0.1517(8) 0.0723(5) 0.0366(18) Uani 1 1 d . . H13 H 0.5775 0.2469 0.0625 0.044 Uiso 1 1 calc R U C14 C 0.5035(8) 0.0642(8) 0.1437(5) 0.0315(17) Uani 1 1 d . . C15 C 0.6736(9) 0.1213(9) 0.2046(5) 0.0379(19) Uani 1 1 d . . C16 C 0.5592(8) -0.1142(8) 0.2923(6) 0.0376(19) Uani 1 1 d . . C17 C 0.8556(8) 0.0757(9) 0.3331(5) 0.043(2) Uani 1 1 d . . H17A H 0.8398 0.0507 0.4045 0.052 Uiso 1 1 calc R U H17B H 0.9238 0.1887 0.3359 0.052 Uiso 1 1 calc R U C18 C 0.9509(8) -0.0056(8) 0.2820(5) 0.0410(19) Uani 1 1 d . . H18A H 0.9674 0.0201 0.2108 0.049 Uiso 1 1 calc R U H18B H 0.8820 -0.1187 0.2786 0.049 Uiso 1 1 calc R U C19 C 1.1244(8) 0.0436(8) 0.3423(5) 0.0373(18) Uani 1 1 d . . H19A H 1.1103 0.0439 0.4166 0.045 Uiso 1 1 calc R U H19B H 1.1641 -0.0340 0.3226 0.045 Uiso 1 1 calc R U C20 C 1.2604(8) 0.2024(8) 0.3243(6) 0.044(2) Uani 1 1 d . . H20A H 1.2196 0.2798 0.3416 0.053 Uiso 1 1 calc R U H20B H 1.2783 0.2012 0.2505 0.053 Uiso 1 1 calc R U C21 C 1.4310(8) 0.2514(8) 0.3884(5) 0.0400(19) Uani 1 1 d . . H21A H 1.4117 0.2495 0.4620 0.048 Uiso 1 1 calc R U H21B H 1.4720 0.1745 0.3699 0.048 Uiso 1 1 calc R U C22 C 1.5668(8) 0.4079(8) 0.3748(6) 0.049(2) Uani 1 1 d . . H22A H 1.5249 0.4846 0.3919 0.059 Uiso 1 1 calc R U H22B H 1.5879 0.4091 0.3016 0.059 Uiso 1 1 calc R U C23 C 1.7355(8) 0.4579(9) 0.4405(6) 0.052(2) Uani 1 1 d . . H23A H 1.7136 0.4503 0.5135 0.062 Uiso 1 1 calc R U H23B H 1.7818 0.3855 0.4202 0.062 Uiso 1 1 calc R U C24 C 1.8690(9) 0.6223(8) 0.4309(6) 0.057(2) Uani 1 1 d . . H24A H 1.8933 0.6306 0.3591 0.085 Uiso 1 1 calc R U H24B H 1.9732 0.6460 0.4743 0.085 Uiso 1 1 calc R U H24C H 1.8261 0.6954 0.4532 0.085 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 0.0120(8) 0.0455(13) 0.0546(14) 0.0020(10) 0.0014(8) 0.0106(8) O1 0.024(3) 0.076(4) 0.065(4) 0.026(3) 0.008(3) 0.026(3) O2 0.017(3) 0.044(3) 0.070(4) 0.001(3) 0.004(3) 0.012(3) N1 0.014(3) 0.043(4) 0.056(4) 0.002(3) 0.000(3) 0.014(3) C1 0.020(3) 0.036(4) 0.030(4) 0.000(3) -0.003(3) 0.005(3) C2 0.019(3) 0.051(5) 0.031(4) 0.005(4) 0.001(3) 0.013(3) C3 0.014(3) 0.054(5) 0.053(5) -0.002(4) 0.010(3) 0.019(4) C4 0.010(3) 0.044(5) 0.036(5) 0.004(4) -0.001(3) 0.012(3) C5 0.019(4) 0.043(5) 0.058(5) -0.006(4) 0.002(4) 0.022(4) C6 0.020(4) 0.052(5) 0.065(6) 0.008(5) 0.007(4) 0.021(4) C7 0.021(4) 0.049(5) 0.053(5) -0.001(4) 0.000(3) 0.021(4) C8 0.021(4) 0.041(5) 0.048(5) 0.001(4) 0.008(3) 0.017(4) C9 0.019(3) 0.032(4) 0.051(5) 0.000(4) 0.006(3) 0.015(3) C10 0.014(3) 0.040(5) 0.048(5) 0.003(4) 0.004(3) 0.012(3) C11 0.022(4) 0.041(5) 0.049(5) 0.006(4) 0.005(3) 0.017(4) C12 0.023(4) 0.044(5) 0.048(5) -0.002(4) -0.005(3) 0.024(4) C13 0.020(4) 0.032(4) 0.057(5) 0.009(4) 0.008(3) 0.010(3) C14 0.019(3) 0.035(4) 0.039(5) 0.001(4) 0.002(3) 0.011(3) C15 0.026(4) 0.049(5) 0.040(5) 0.001(4) 0.001(4) 0.019(4) C16 0.022(4) 0.047(5) 0.045(5) 0.010(4) 0.006(4) 0.015(4) C17 0.019(4) 0.064(5) 0.049(5) -0.006(4) -0.003(3) 0.024(4) C18 0.018(4) 0.044(5) 0.056(5) -0.008(4) -0.006(3) 0.014(4) C19 0.020(4) 0.049(5) 0.042(5) -0.001(4) -0.001(3) 0.016(4) C20 0.024(4) 0.060(5) 0.053(5) 0.004(4) 0.005(4) 0.024(4) C21 0.024(4) 0.068(5) 0.040(5) 0.011(4) 0.004(3) 0.031(4) C22 0.014(3) 0.064(5) 0.062(6) 0.003(4) 0.001(4) 0.012(4) C23 0.021(4) 0.077(6) 0.058(6) -0.007(5) -0.002(4) 0.026(4) C24 0.028(4) 0.066(6) 0.071(6) -0.004(5) 0.005(4) 0.019(4) 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 C1 S1 C4 91.3(3) . . C16 N1 C15 127.0(6) . . C16 N1 C17 115.6(6) . . C15 N1 C17 117.4(6) . . C2 C1 C1 128.7(7) . 2_445 C2 C1 S1 111.8(5) . . C1 C1 S1 119.4(6) 2_445 . C1 C2 C3 112.8(6) . . C1 C2 H2 123.6 . . C3 C2 H2 123.6 . . C4 C3 C2 112.9(6) . . C4 C3 H3 123.5 . . C2 C3 H3 123.5 . . C3 C4 C5 130.2(6) . . C3 C4 S1 111.2(5) . . C5 C4 S1 118.5(5) . . C6 C5 C10 120.0(6) . . C6 C5 C4 120.6(6) . . C10 C5 C4 119.4(7) . . C5 C6 C7 120.9(7) . . C5 C6 H6 119.5 . . C7 C6 H6 119.5 . . C8 C7 C6 120.4(7) . . C8 C7 H7 119.8 . . C6 C7 H7 119.8 . . C7 C8 C9 120.7(6) . . C7 C8 C16 119.6(7) . . C9 C8 C16 119.7(6) . . C14 C9 C8 121.2(6) . . C14 C9 C10 119.5(6) . . C8 C9 C10 119.3(6) . . C11 C10 C5 124.6(6) . . C11 C10 C9 117.0(6) . . C5 C10 C9 118.4(6) . . C12 C11 C10 122.6(7) . . C12 C11 H11 118.7 . . C10 C11 H11 118.7 . . C11 C12 C13 120.2(7) . . C11 C12 H12 119.9 . . C13 C12 H12 119.9 . . C14 C13 C12 119.1(6) . . C14 C13 H13 120.4 . . C12 C13 H13 120.4 . . C13 C14 C9 121.6(6) . . C13 C14 C15 118.5(6) . . C9 C14 C15 119.8(6) . . O2 C15 N1 122.2(6) . . O2 C15 C14 121.9(7) . . N1 C15 C14 115.9(6) . . O1 C16 N1 122.4(7) . . O1 C16 C8 121.3(6) . . N1 C16 C8 116.3(7) . . N1 C17 C18 110.8(5) . . N1 C17 H17A 109.5 . . C18 C17 H17A 109.5 . . N1 C17 H17B 109.5 . . C18 C17 H17B 109.5 . . H17A C17 H17B 108.1 . . C17 C18 C19 111.2(6) . . C17 C18 H18A 109.4 . . C19 C18 H18A 109.4 . . C17 C18 H18B 109.4 . . C19 C18 H18B 109.4 . . H18A C18 H18B 108.0 . . C20 C19 C18 114.0(6) . . C20 C19 H19A 108.7 . . C18 C19 H19A 108.7 . . C20 C19 H19B 108.7 . . C18 C19 H19B 108.7 . . H19A C19 H19B 107.6 . . C19 C20 C21 113.0(6) . . C19 C20 H20A 109.0 . . C21 C20 H20A 109.0 . . C19 C20 H20B 109.0 . . C21 C20 H20B 109.0 . . H20A C20 H20B 107.8 . . C22 C21 C20 114.8(6) . . C22 C21 H21A 108.6 . . C20 C21 H21A 108.6 . . C22 C21 H21B 108.6 . . C20 C21 H21B 108.6 . . H21A C21 H21B 107.6 . . C21 C22 C23 114.7(6) . . C21 C22 H22A 108.6 . . C23 C22 H22A 108.6 . . C21 C22 H22B 108.6 . . C23 C22 H22B 108.6 . . H22A C22 H22B 107.6 . . C24 C23 C22 113.9(6) . . C24 C23 H23A 108.8 . . C22 C23 H23A 108.8 . . C24 C23 H23B 108.8 . . C22 C23 H23B 108.8 . . H23A C23 H23B 107.7 . . C23 C24 H24A 109.5 . . C23 C24 H24B 109.5 . . H24A C24 H24B 109.5 . . C23 C24 H24C 109.5 . . H24A C24 H24C 109.5 . . H24B C24 H24C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C1 1.729(7) . S1 C4 1.741(7) . O1 C16 1.206(7) . O2 C15 1.218(8) . N1 C16 1.376(8) . N1 C15 1.394(8) . N1 C17 1.505(8) . C1 C2 1.346(9) . C1 C1 1.502(12) 2_445 C2 C3 1.434(9) . C2 H2 0.9500 . C3 C4 1.351(9) . C3 H3 0.9500 . C4 C5 1.492(9) . C5 C6 1.373(9) . C5 C10 1.436(9) . C6 C7 1.423(9) . C6 H6 0.9500 . C7 C8 1.375(9) . C7 H7 0.9500 . C8 C9 1.412(9) . C8 C16 1.503(9) . C9 C14 1.407(9) . C9 C10 1.451(9) . C10 C11 1.411(9) . C11 C12 1.362(9) . C11 H11 0.9500 . C12 C13 1.431(9) . C12 H12 0.9500 . C13 C14 1.373(9) . C13 H13 0.9500 . C14 C15 1.505(9) . C17 C18 1.538(9) . C17 H17A 0.9900 . C17 H17B 0.9900 . C18 C19 1.539(9) . C18 H18A 0.9900 . C18 H18B 0.9900 . C19 C20 1.529(9) . C19 H19A 0.9900 . C19 H19B 0.9900 . C20 C21 1.540(9) . C20 H20A 0.9900 . C20 H20B 0.9900 . C21 C22 1.497(9) . C21 H21A 0.9900 . C21 H21B 0.9900 . C22 C23 1.535(9) . C22 H22A 0.9900 . C22 H22B 0.9900 . C23 C24 1.532(9) . C23 H23A 0.9900 . C23 H23B 0.9900 . C24 H24A 0.9800 . C24 H24B 0.9800 . C24 H24C 0.9800 . 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_4 C4 S1 C1 C2 0.0(6) . . C4 S1 C1 C1 -176.4(7) . 2_445 C1 C1 C2 C3 176.6(8) 2_445 . S1 C1 C2 C3 0.6(8) . . C1 C2 C3 C4 -1.0(9) . . C2 C3 C4 C5 175.9(7) . . C2 C3 C4 S1 1.0(8) . . C1 S1 C4 C3 -0.6(6) . . C1 S1 C4 C5 -176.1(6) . . C3 C4 C5 C6 -130.7(8) . . S1 C4 C5 C6 43.8(9) . . C3 C4 C5 C10 52.4(10) . . S1 C4 C5 C10 -133.0(6) . . C10 C5 C6 C7 -6.0(10) . . C4 C5 C6 C7 177.2(6) . . C5 C6 C7 C8 3.1(11) . . C6 C7 C8 C9 0.5(10) . . C6 C7 C8 C16 -178.1(6) . . C7 C8 C9 C14 176.7(6) . . C16 C8 C9 C14 -4.7(10) . . C7 C8 C9 C10 -0.9(10) . . C16 C8 C9 C10 177.6(6) . . C6 C5 C10 C11 -175.4(7) . . C4 C5 C10 C11 1.5(10) . . C6 C5 C10 C9 5.4(10) . . C4 C5 C10 C9 -177.7(6) . . C14 C9 C10 C11 1.1(9) . . C8 C9 C10 C11 178.8(6) . . C14 C9 C10 C5 -179.7(6) . . C8 C9 C10 C5 -2.0(10) . . C5 C10 C11 C12 -179.2(7) . . C9 C10 C11 C12 0.0(10) . . C10 C11 C12 C13 -0.6(10) . . C11 C12 C13 C14 0.1(10) . . C12 C13 C14 C9 0.9(10) . . C12 C13 C14 C15 179.1(6) . . C8 C9 C14 C13 -179.2(7) . . C10 C9 C14 C13 -1.5(10) . . C8 C9 C14 C15 2.6(10) . . C10 C9 C14 C15 -179.7(6) . . C16 N1 C15 O2 -178.8(7) . . C17 N1 C15 O2 -1.8(10) . . C16 N1 C15 C14 0.4(10) . . C17 N1 C15 C14 177.4(6) . . C13 C14 C15 O2 0.6(10) . . C9 C14 C15 O2 178.8(7) . . C13 C14 C15 N1 -178.6(6) . . C9 C14 C15 N1 -0.3(9) . . C15 N1 C16 O1 178.7(7) . . C17 N1 C16 O1 1.7(10) . . C15 N1 C16 C8 -2.4(10) . . C17 N1 C16 C8 -179.4(6) . . C7 C8 C16 O1 2.0(11) . . C9 C8 C16 O1 -176.6(7) . . C7 C8 C16 N1 -177.0(6) . . C9 C8 C16 N1 4.5(9) . . C16 N1 C17 C18 80.0(8) . . C15 N1 C17 C18 -97.4(7) . . N1 C17 C18 C19 -179.5(6) . . C17 C18 C19 C20 -77.5(8) . . C18 C19 C20 C21 177.9(6) . . C19 C20 C21 C22 -178.8(6) . . C20 C21 C22 C23 178.8(6) . . C21 C22 C23 C24 -176.2(6) . .