#------------------------------------------------------------------------------ #$Date: 2026-06-29 23:18:01 +0100 (Mon, 29 Jun 2026) $ #$Revision: 306676 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577456.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_1577456 loop_ _publ_author_name 'Shaikh, Aslam C.' 'Kaur, Kavneet' 'SINGH, PUJA' 'Thombare, Rahul D.' 'P., Adithya K.' 'Mane, Manoj V.' _publ_section_title ; Stereoselective Dearomative Formal [3+2] cycloaddition of Indole with Allenols: Access to Structurally Diverse Cyclopenta[b]indoles ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC03994D _journal_year 2026 _chemical_absolute_configuration NA _chemical_formula_sum 'C28 H27 N O3 S' _chemical_formula_weight 457.56 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2019/1 _audit_update_record ; 2025-12-10 deposited with the CCDC. 2026-06-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.689(6) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.190(2) _cell_length_b 7.9615(14) _cell_length_c 13.430(2) _cell_measurement_reflns_used 3249 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 18.22 _cell_measurement_theta_min 2.59 _cell_volume 1179.4(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2019/1 (Sheldrick, 2019)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.995 _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 0.0990 _diffrn_reflns_av_unetI/netI 0.0874 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 34314 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.530 _diffrn_reflns_theta_min 2.595 _diffrn_source Mo _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS-2016/2 _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.288 _exptl_crystal_description 'Block type' _exptl_crystal_F_000 484 _exptl_crystal_size_max 0.193 _exptl_crystal_size_mid 0.145 _exptl_crystal_size_min 0.122 _exptl_transmission_factor_max 0.7457 _exptl_transmission_factor_min 0.6094 _refine_diff_density_max 0.171 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details ; Flack x determined using 1172 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.04(6) _refine_ls_extinction_coef 0.033(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/1 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 302 _refine_ls_number_reflns 5957 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.953 _refine_ls_R_factor_all 0.1178 _refine_ls_R_factor_gt 0.0540 _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^)+(0.0636P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1127 _refine_ls_wR_factor_ref 0.1369 _reflns_Friedel_coverage 0.867 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.993 _reflns_number_gt 3336 _reflns_number_total 5957 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc03994d2.cif _cod_data_source_block acs_kav1_0m_a _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_original_cell_volume 1179.4(4) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1577456 _shelx_shelxl_version_number 2019/1 _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_res_file ; TITL ACS_KAV1_0m_a.res in P2(1) acs_kav1_0m_a.res created by SHELXL-2019/1 at 14:26:26 on 09-Dec-2025 CELL 0.71073 11.1901 7.9615 13.4302 90 99.689 90 ZERR 2 0.002 0.0014 0.0023 0 0.006 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O S UNIT 56 54 2 6 2 L.S. 10 PLAN 2 TEMP 0 CONF BOND fmap 2 acta MORE -1 BOND $H OMIT 0 0 1 REM REM REM WGHT 0.063600 EXTI 0.033128 FVAR 1.00221 S1 5 0.782638 0.324231 0.774217 11.00000 0.05616 0.04837 = 0.04583 0.00228 0.00661 0.00799 O2 4 0.695930 0.189147 0.767339 11.00000 0.07516 0.04574 = 0.06938 0.00504 0.02357 -0.00362 O1 4 0.884965 0.323810 0.853992 11.00000 0.06855 0.08082 = 0.05142 -0.00162 -0.00884 0.02600 O3 4 0.682933 0.705788 0.313572 11.00000 0.08193 0.06936 = 0.04588 0.00582 0.01747 -0.01045 N1 3 0.574541 0.807790 0.917283 11.00000 0.06280 0.07698 = 0.08209 -0.04245 0.01621 -0.00679 AFIX 43 H1 2 0.606810 0.871860 0.966029 11.00000 -1.20000 AFIX 0 C22 1 0.836357 0.334634 0.659123 11.00000 0.03978 0.04496 = 0.05101 -0.00444 0.00634 0.00206 C16 1 0.530588 0.531847 0.513229 11.00000 0.04210 0.04436 = 0.04601 -0.00163 0.00776 -0.00378 AFIX 43 H16 2 0.463906 0.466180 0.520621 11.00000 -1.20000 AFIX 0 C15 1 0.606625 0.586074 0.598772 11.00000 0.03959 0.04256 = 0.04102 0.00180 0.00525 -0.00029 C28 1 0.769185 0.269188 0.572243 11.00000 0.04746 0.05455 = 0.05991 -0.00326 0.01101 0.00106 AFIX 43 H28 2 0.697973 0.210707 0.575389 11.00000 -1.20000 AFIX 0 C17 1 0.549751 0.571524 0.416438 11.00000 0.04873 0.04114 = 0.04408 -0.00203 0.00196 0.00113 AFIX 43 H17 2 0.495606 0.535437 0.360266 11.00000 -1.20000 AFIX 0 C18 1 0.650246 0.665236 0.404754 11.00000 0.05752 0.04456 = 0.04333 0.00751 0.01538 0.00668 C14 1 0.583228 0.539769 0.703837 11.00000 0.04733 0.03902 = 0.04211 0.00110 0.00922 0.00214 AFIX 13 H14 2 0.530565 0.440821 0.700091 11.00000 -1.20000 AFIX 0 C7 1 0.524831 0.688788 0.753313 11.00000 0.05215 0.03862 = 0.05082 0.00125 0.00829 0.00523 AFIX 13 H7 2 0.491339 0.770553 0.701515 11.00000 -1.20000 AFIX 0 C1 1 0.465799 0.727599 0.912776 11.00000 0.05396 0.05062 = 0.04552 -0.00402 0.00404 0.01206 C13 1 0.698523 0.509661 0.779554 11.00000 0.04934 0.04741 = 0.03905 0.00220 0.00554 0.00505 C5 1 0.323661 0.563258 0.799566 11.00000 0.05584 0.05799 = 0.05077 -0.00534 0.00594 0.00151 AFIX 43 H5 2 0.301064 0.509630 0.737746 11.00000 -1.20000 AFIX 0 C20 1 0.726161 0.724579 0.489433 11.00000 0.04905 0.05241 = 0.05470 0.00548 0.00906 -0.00849 AFIX 43 H20 2 0.793110 0.789763 0.482135 11.00000 -1.20000 AFIX 0 C6 1 0.432226 0.648932 0.819969 11.00000 0.05082 0.04034 = 0.04213 0.00101 0.00922 0.00924 C23 1 0.943160 0.418244 0.653187 11.00000 0.05026 0.05986 = 0.06646 -0.00806 0.00924 0.00333 AFIX 43 H23 2 0.989740 0.461424 0.711452 11.00000 -1.20000 AFIX 0 C8 1 0.628140 0.770297 0.828838 11.00000 0.05587 0.04496 = 0.06622 -0.00652 0.00774 -0.00124 AFIX 13 H8 2 0.657859 0.872625 0.800616 11.00000 -1.20000 AFIX 0 C9 1 0.726363 0.635384 0.845796 11.00000 0.04841 0.04680 = 0.04641 -0.00097 0.00953 -0.00431 C27 1 0.807971 0.290655 0.479784 11.00000 0.06683 0.06040 = 0.05075 -0.00433 0.00905 0.01422 AFIX 43 H27 2 0.762271 0.245306 0.421766 11.00000 -1.20000 AFIX 0 C25 1 0.912602 0.377648 0.472459 11.00000 0.07006 0.05717 = 0.06861 0.00478 0.03077 0.01801 C2 1 0.388867 0.725278 0.984320 11.00000 0.06948 0.07426 = 0.04329 -0.00187 0.00858 0.02401 AFIX 43 H2 2 0.409799 0.780998 1.045638 11.00000 -1.20000 AFIX 0 C3 1 0.281515 0.638891 0.962220 11.00000 0.07579 0.08069 = 0.05586 0.00914 0.02289 0.02041 AFIX 43 H3 2 0.229975 0.635441 1.009757 11.00000 -1.20000 AFIX 0 C21 1 0.702875 0.687330 0.584953 11.00000 0.04893 0.05087 = 0.04402 -0.00030 0.00063 -0.00454 AFIX 43 H21 2 0.753079 0.731380 0.641116 11.00000 -1.20000 AFIX 0 C10 1 0.833286 0.664728 0.926126 11.00000 0.05938 0.06337 = 0.05647 -0.01292 0.00598 -0.00271 C24 1 0.981034 0.437997 0.561405 11.00000 0.05232 0.05825 = 0.09337 -0.00438 0.02902 -0.00251 AFIX 43 H24 2 1.053852 0.492808 0.558867 11.00000 -1.20000 AFIX 0 C4 1 0.248353 0.557479 0.871704 11.00000 0.05719 0.07089 = 0.07098 -0.00164 0.02151 0.00190 AFIX 43 H4 2 0.175612 0.498602 0.858751 11.00000 -1.20000 AFIX 0 C19 1 0.619652 0.627565 0.224479 11.00000 0.11640 0.08063 = 0.04450 -0.00230 0.02381 -0.00755 AFIX 137 H19A 2 0.636939 0.509388 0.226644 11.00000 -1.50000 H19B 2 0.645378 0.676185 0.166180 11.00000 -1.50000 H19C 2 0.534061 0.644492 0.220666 11.00000 -1.50000 AFIX 0 C12 1 0.926853 0.775268 0.899375 11.00000 0.07973 0.12959 = 0.09225 -0.00423 -0.00718 -0.04088 AFIX 137 H12A 2 0.985679 0.798482 0.958475 11.00000 -1.50000 H12B 2 0.890552 0.878543 0.872551 11.00000 -1.50000 H12C 2 0.965927 0.721548 0.849487 11.00000 -1.50000 AFIX 0 C26 1 0.950195 0.409154 0.371611 11.00000 0.11432 0.10123 = 0.08691 0.02109 0.05579 0.02814 AFIX 137 H26A 2 0.977484 0.305962 0.346026 11.00000 -1.50000 H26B 2 1.014773 0.489959 0.379362 11.00000 -1.50000 H26C 2 0.882301 0.451631 0.325131 11.00000 -1.50000 AFIX 0 C11 1 0.836766 0.603797 1.020494 11.00000 0.09291 0.08673 = 0.05726 -0.00755 -0.00390 -0.01162 AFIX 93 H11A 2 0.900649 0.632077 1.071417 11.00000 -1.20000 H11B 2 0.775277 0.533587 1.034508 11.00000 -1.20000 AFIX 0 HKLF 4 REM ACS_KAV1_0m_a.res in P2(1) REM wR2 = 0.1369, GooF = S = 0.954, Restrained GooF = 0.953 for all data REM R1 = 0.0540 for 3336 Fo > 4sig(Fo) and 0.1178 for all 5957 data REM 302 parameters refined using 1 restraints END WGHT 0.0636 0.0000 REM Highest difference peak 0.171, deepest hole -0.228, 1-sigma level 0.042 Q1 1 0.6668 0.3212 0.6823 11.00000 0.05 0.17 Q2 1 0.7353 0.2273 0.6819 11.00000 0.05 0.17 ; _shelx_res_checksum 45988 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 S1 S 0.78264(10) 0.32423(13) 0.77422(8) 0.0504(3) Uani 1 1 d . . . . . O2 O 0.6959(3) 0.1891(4) 0.7673(2) 0.0621(9) Uani 1 1 d . . . . . O1 O 0.8850(3) 0.3238(5) 0.8540(2) 0.0691(9) Uani 1 1 d . . . . . O3 O 0.6829(3) 0.7058(4) 0.3136(2) 0.0649(9) Uani 1 1 d . . . . . N1 N 0.5745(4) 0.8078(6) 0.9173(3) 0.0735(12) Uani 1 1 d . . . . . H1 H 0.606810 0.871860 0.966029 0.088 Uiso 1 1 calc R U . . . C22 C 0.8364(4) 0.3346(6) 0.6591(3) 0.0454(9) Uani 1 1 d . . . . . C16 C 0.5306(4) 0.5318(5) 0.5132(3) 0.0441(10) Uani 1 1 d . . . . . H16 H 0.463906 0.466180 0.520621 0.053 Uiso 1 1 calc R U . . . C15 C 0.6066(4) 0.5861(5) 0.5988(3) 0.0412(9) Uani 1 1 d . . . . . C28 C 0.7692(4) 0.2692(5) 0.5722(3) 0.0537(12) Uani 1 1 d . . . . . H28 H 0.697973 0.210707 0.575389 0.064 Uiso 1 1 calc R U . . . C17 C 0.5498(4) 0.5715(5) 0.4164(3) 0.0453(10) Uani 1 1 d . . . . . H17 H 0.495606 0.535437 0.360266 0.054 Uiso 1 1 calc R U . . . C18 C 0.6502(4) 0.6652(5) 0.4048(3) 0.0477(10) Uani 1 1 d . . . . . C14 C 0.5832(4) 0.5398(5) 0.7038(3) 0.0426(10) Uani 1 1 d . . . . . H14 H 0.530565 0.440821 0.700091 0.051 Uiso 1 1 calc R U . . . C7 C 0.5248(4) 0.6888(5) 0.7533(3) 0.0472(10) Uani 1 1 d . . . . . H7 H 0.491339 0.770553 0.701515 0.057 Uiso 1 1 calc R U . . . C1 C 0.4658(4) 0.7276(5) 0.9128(3) 0.0505(11) Uani 1 1 d . . . . . C13 C 0.6985(4) 0.5097(5) 0.7796(3) 0.0455(10) Uani 1 1 d . . . . . C5 C 0.3237(4) 0.5633(6) 0.7996(3) 0.0552(12) Uani 1 1 d . . . . . H5 H 0.301064 0.509630 0.737746 0.066 Uiso 1 1 calc R U . . . C20 C 0.7262(4) 0.7246(5) 0.4894(3) 0.0520(11) Uani 1 1 d . . . . . H20 H 0.793110 0.789763 0.482135 0.062 Uiso 1 1 calc R U . . . C6 C 0.4322(4) 0.6489(5) 0.8200(3) 0.0443(10) Uani 1 1 d . . . . . C23 C 0.9432(4) 0.4182(6) 0.6532(4) 0.0589(12) Uani 1 1 d . . . . . H23 H 0.989740 0.461424 0.711452 0.071 Uiso 1 1 calc R U . . . C8 C 0.6281(4) 0.7703(5) 0.8288(3) 0.0560(12) Uani 1 1 d . . . . . H8 H 0.657859 0.872625 0.800616 0.067 Uiso 1 1 calc R U . . . C9 C 0.7264(4) 0.6354(5) 0.8458(3) 0.0470(10) Uani 1 1 d . . . . . C27 C 0.8080(5) 0.2907(5) 0.4798(3) 0.0594(13) Uani 1 1 d . . . . . H27 H 0.762271 0.245306 0.421766 0.071 Uiso 1 1 calc R U . . . C25 C 0.9126(5) 0.3776(6) 0.4725(4) 0.0631(13) Uani 1 1 d . . . . . C2 C 0.3889(5) 0.7253(7) 0.9843(3) 0.0624(13) Uani 1 1 d . . . . . H2 H 0.409799 0.780998 1.045638 0.075 Uiso 1 1 calc R U . . . C3 C 0.2815(5) 0.6389(7) 0.9622(4) 0.0694(14) Uani 1 1 d . . . . . H3 H 0.229975 0.635441 1.009757 0.083 Uiso 1 1 calc R U . . . C21 C 0.7029(4) 0.6873(5) 0.5850(3) 0.0488(10) Uani 1 1 d . . . . . H21 H 0.753079 0.731380 0.641116 0.059 Uiso 1 1 calc R U . . . C10 C 0.8333(4) 0.6647(6) 0.9261(4) 0.0602(12) Uani 1 1 d . . . . . C24 C 0.9810(5) 0.4380(6) 0.5614(4) 0.0660(14) Uani 1 1 d . . . . . H24 H 1.053852 0.492808 0.558867 0.079 Uiso 1 1 calc R U . . . C4 C 0.2484(5) 0.5575(7) 0.8717(4) 0.0651(13) Uani 1 1 d . . . . . H4 H 0.175612 0.498602 0.858751 0.078 Uiso 1 1 calc R U . . . C19 C 0.6197(6) 0.6276(7) 0.2245(3) 0.0793(16) Uani 1 1 d . . . . . H19A H 0.636939 0.509388 0.226644 0.119 Uiso 1 1 calc R U . . . H19B H 0.645378 0.676185 0.166180 0.119 Uiso 1 1 calc R U . . . H19C H 0.534061 0.644492 0.220666 0.119 Uiso 1 1 calc R U . . . C12 C 0.9269(5) 0.7753(9) 0.8994(5) 0.103(2) Uani 1 1 d . . . . . H12A H 0.985679 0.798482 0.958475 0.155 Uiso 1 1 calc R U . . . H12B H 0.890552 0.878543 0.872551 0.155 Uiso 1 1 calc R U . . . H12C H 0.965927 0.721548 0.849487 0.155 Uiso 1 1 calc R U . . . C26 C 0.9502(6) 0.4092(8) 0.3716(4) 0.096(2) Uani 1 1 d . . . . . H26A H 0.977484 0.305962 0.346026 0.145 Uiso 1 1 calc R U . . . H26B H 1.014773 0.489959 0.379362 0.145 Uiso 1 1 calc R U . . . H26C H 0.882301 0.451631 0.325131 0.145 Uiso 1 1 calc R U . . . C11 C 0.8368(6) 0.6038(7) 1.0205(4) 0.0809(16) Uani 1 1 d . . . . . H11A H 0.900649 0.632077 1.071417 0.097 Uiso 1 1 calc R U . . . H11B H 0.775277 0.533587 1.034508 0.097 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 0.0562(7) 0.0484(5) 0.0458(6) 0.0023(5) 0.0066(5) 0.0080(6) O2 0.075(2) 0.0457(17) 0.069(2) 0.0050(15) 0.0236(18) -0.0036(16) O1 0.069(2) 0.081(2) 0.0514(17) -0.0016(18) -0.0088(16) 0.026(2) O3 0.082(2) 0.069(2) 0.0459(17) 0.0058(15) 0.0175(17) -0.0104(18) N1 0.063(3) 0.077(3) 0.082(3) -0.042(2) 0.016(2) -0.007(2) C22 0.040(2) 0.045(2) 0.051(2) -0.004(2) 0.0063(19) 0.002(2) C16 0.042(3) 0.044(2) 0.046(2) -0.0016(18) 0.008(2) -0.0038(18) C15 0.040(2) 0.043(2) 0.041(2) 0.0018(17) 0.0053(19) -0.0003(18) C28 0.047(3) 0.055(3) 0.060(3) -0.003(2) 0.011(2) 0.001(2) C17 0.049(3) 0.041(2) 0.044(2) -0.0020(17) 0.002(2) 0.0011(19) C18 0.058(3) 0.045(2) 0.043(2) 0.0075(19) 0.015(2) 0.007(2) C14 0.047(3) 0.039(2) 0.042(2) 0.0011(16) 0.0092(19) 0.0021(18) C7 0.052(3) 0.039(2) 0.051(2) 0.0013(18) 0.008(2) 0.0052(19) C1 0.054(3) 0.051(2) 0.046(2) -0.0040(19) 0.004(2) 0.012(2) C13 0.049(3) 0.047(2) 0.039(2) 0.0022(18) 0.006(2) 0.0050(19) C5 0.056(3) 0.058(3) 0.051(3) -0.005(2) 0.006(2) 0.002(2) C20 0.049(3) 0.052(2) 0.055(3) 0.005(2) 0.009(2) -0.008(2) C6 0.051(3) 0.040(2) 0.042(2) 0.0010(17) 0.009(2) 0.0092(19) C23 0.050(3) 0.060(3) 0.066(3) -0.008(2) 0.009(3) 0.003(2) C8 0.056(3) 0.045(2) 0.066(3) -0.007(2) 0.008(2) -0.001(2) C9 0.048(3) 0.047(2) 0.046(2) -0.0010(18) 0.010(2) -0.004(2) C27 0.067(3) 0.060(3) 0.051(3) -0.004(2) 0.009(2) 0.014(2) C25 0.070(4) 0.057(3) 0.069(3) 0.005(2) 0.031(3) 0.018(3) C2 0.069(4) 0.074(3) 0.043(3) -0.002(2) 0.009(3) 0.024(3) C3 0.076(4) 0.081(3) 0.056(3) 0.009(3) 0.023(3) 0.020(3) C21 0.049(3) 0.051(2) 0.044(2) -0.0003(19) 0.001(2) -0.005(2) C10 0.059(3) 0.063(3) 0.056(3) -0.013(2) 0.006(2) -0.003(2) C24 0.052(3) 0.058(3) 0.093(4) -0.004(3) 0.029(3) -0.003(2) C4 0.057(3) 0.071(3) 0.071(3) -0.002(3) 0.022(3) 0.002(2) C19 0.116(5) 0.081(3) 0.044(3) -0.002(3) 0.024(3) -0.008(3) C12 0.080(4) 0.130(6) 0.092(4) -0.004(4) -0.007(3) -0.041(4) C26 0.114(5) 0.101(4) 0.087(4) 0.021(3) 0.056(4) 0.028(4) C11 0.093(4) 0.087(4) 0.057(3) -0.008(3) -0.004(3) -0.012(3) 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 O1 S1 O2 119.5(2) . . ? O1 S1 C22 108.10(19) . . ? O2 S1 C22 107.8(2) . . ? O1 S1 C13 109.7(2) . . ? O2 S1 C13 105.66(18) . . ? C22 S1 C13 105.2(2) . . ? C18 O3 C19 118.4(4) . . ? C1 N1 C8 110.8(4) . . ? C1 N1 H1 124.6 . . ? C8 N1 H1 124.6 . . ? C28 C22 C23 119.1(4) . . ? C28 C22 S1 120.6(3) . . ? C23 C22 S1 120.1(3) . . ? C15 C16 C17 122.5(4) . . ? C15 C16 H16 118.7 . . ? C17 C16 H16 118.7 . . ? C16 C15 C21 117.1(4) . . ? C16 C15 C14 121.2(4) . . ? C21 C15 C14 121.7(3) . . ? C22 C28 C27 120.0(4) . . ? C22 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? C18 C17 C16 119.1(4) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? O3 C18 C17 124.9(4) . . ? O3 C18 C20 115.7(4) . . ? C17 C18 C20 119.4(4) . . ? C13 C14 C15 113.5(3) . . ? C13 C14 C7 101.8(3) . . ? C15 C14 C7 111.2(3) . . ? C13 C14 H14 110.0 . . ? C15 C14 H14 110.0 . . ? C7 C14 H14 110.0 . . ? C6 C7 C8 102.2(3) . . ? C6 C7 C14 118.1(3) . . ? C8 C7 C14 106.2(3) . . ? C6 C7 H7 109.9 . . ? C8 C7 H7 109.9 . . ? C14 C7 H7 109.9 . . ? N1 C1 C6 110.8(4) . . ? N1 C1 C2 128.6(4) . . ? C6 C1 C2 120.5(5) . . ? C9 C13 C14 113.7(4) . . ? C9 C13 S1 126.0(3) . . ? C14 C13 S1 120.3(3) . . ? C6 C5 C4 119.7(4) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C18 C20 C21 120.2(4) . . ? C18 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C5 C6 C1 119.8(4) . . ? C5 C6 C7 130.8(4) . . ? C1 C6 C7 109.1(4) . . ? C24 C23 C22 120.4(5) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? N1 C8 C9 114.2(4) . . ? N1 C8 C7 104.9(4) . . ? C9 C8 C7 104.0(3) . . ? N1 C8 H8 111.1 . . ? C9 C8 H8 111.1 . . ? C7 C8 H8 111.1 . . ? C13 C9 C10 131.8(4) . . ? C13 C9 C8 110.2(4) . . ? C10 C9 C8 117.9(4) . . ? C25 C27 C28 121.4(4) . . ? C25 C27 H27 119.3 . . ? C28 C27 H27 119.3 . . ? C27 C25 C24 117.6(4) . . ? C27 C25 C26 121.2(5) . . ? C24 C25 C26 121.2(5) . . ? C3 C2 C1 118.5(4) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C4 C3 C2 121.6(5) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C15 C21 C20 121.5(4) . . ? C15 C21 H21 119.3 . . ? C20 C21 H21 119.3 . . ? C11 C10 C12 122.6(5) . . ? C11 C10 C9 121.1(5) . . ? C12 C10 C9 116.0(4) . . ? C23 C24 C25 121.4(5) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? C3 C4 C5 119.8(5) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? O3 C19 H19A 109.5 . . ? O3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C10 C11 H11A 120.0 . . ? C10 C11 H11B 120.0 . . ? H11A C11 H11B 120.0 . . ? 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 O1 1.430(3) . ? S1 O2 1.441(3) . ? S1 C22 1.752(4) . ? S1 C13 1.759(4) . ? O3 C18 1.374(5) . ? O3 C19 1.427(5) . ? N1 C1 1.366(6) . ? N1 C8 1.449(6) . ? N1 H1 0.8600 . ? C22 C28 1.379(6) . ? C22 C23 1.382(6) . ? C16 C15 1.379(5) . ? C16 C17 1.389(6) . ? C16 H16 0.9300 . ? C15 C21 1.383(5) . ? C15 C14 1.523(5) . ? C28 C27 1.393(6) . ? C28 H28 0.9300 . ? C17 C18 1.380(6) . ? C17 H17 0.9300 . ? C18 C20 1.383(6) . ? C14 C13 1.521(6) . ? C14 C7 1.556(5) . ? C14 H14 0.9800 . ? C7 C6 1.513(6) . ? C7 C8 1.547(6) . ? C7 H7 0.9800 . ? C1 C6 1.389(6) . ? C1 C2 1.394(6) . ? C13 C9 1.341(5) . ? C5 C6 1.380(6) . ? C5 C4 1.388(7) . ? C5 H5 0.9300 . ? C20 C21 1.383(5) . ? C20 H20 0.9300 . ? C23 C24 1.378(7) . ? C23 H23 0.9300 . ? C8 C9 1.526(6) . ? C8 H8 0.9800 . ? C9 C10 1.488(6) . ? C27 C25 1.378(7) . ? C27 H27 0.9300 . ? C25 C24 1.392(7) . ? C25 C26 1.505(7) . ? C2 C3 1.373(7) . ? C2 H2 0.9300 . ? C3 C4 1.373(7) . ? C3 H3 0.9300 . ? C21 H21 0.9300 . ? C10 C11 1.351(6) . ? C10 C12 1.458(7) . ? C24 H24 0.9300 . ? C4 H4 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C11 H11A 0.9300 . ? C11 H11B 0.9300 . ? 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 O1 S1 C22 C28 152.9(4) . . . . ? O2 S1 C22 C28 22.5(4) . . . . ? C13 S1 C22 C28 -89.9(4) . . . . ? O1 S1 C22 C23 -31.3(4) . . . . ? O2 S1 C22 C23 -161.7(4) . . . . ? C13 S1 C22 C23 85.9(4) . . . . ? C17 C16 C15 C21 1.8(6) . . . . ? C17 C16 C15 C14 -179.8(4) . . . . ? C23 C22 C28 C27 -1.3(7) . . . . ? S1 C22 C28 C27 174.6(3) . . . . ? C15 C16 C17 C18 1.7(6) . . . . ? C19 O3 C18 C17 -9.3(6) . . . . ? C19 O3 C18 C20 170.5(4) . . . . ? C16 C17 C18 O3 176.6(4) . . . . ? C16 C17 C18 C20 -3.2(6) . . . . ? C16 C15 C14 C13 144.2(4) . . . . ? C21 C15 C14 C13 -37.4(5) . . . . ? C16 C15 C14 C7 -101.8(4) . . . . ? C21 C15 C14 C7 76.6(4) . . . . ? C13 C14 C7 C6 -94.2(4) . . . . ? C15 C14 C7 C6 144.6(3) . . . . ? C13 C14 C7 C8 19.6(4) . . . . ? C15 C14 C7 C8 -101.6(4) . . . . ? C8 N1 C1 C6 -6.6(5) . . . . ? C8 N1 C1 C2 177.0(4) . . . . ? C15 C14 C13 C9 105.0(4) . . . . ? C7 C14 C13 C9 -14.6(4) . . . . ? C15 C14 C13 S1 -74.4(4) . . . . ? C7 C14 C13 S1 166.0(3) . . . . ? O1 S1 C13 C9 1.8(5) . . . . ? O2 S1 C13 C9 131.9(4) . . . . ? C22 S1 C13 C9 -114.2(4) . . . . ? O1 S1 C13 C14 -178.8(3) . . . . ? O2 S1 C13 C14 -48.8(3) . . . . ? C22 S1 C13 C14 65.1(4) . . . . ? O3 C18 C20 C21 -178.5(4) . . . . ? C17 C18 C20 C21 1.3(6) . . . . ? C4 C5 C6 C1 0.5(6) . . . . ? C4 C5 C6 C7 -173.7(4) . . . . ? N1 C1 C6 C5 -178.8(4) . . . . ? C2 C1 C6 C5 -2.1(6) . . . . ? N1 C1 C6 C7 -3.5(5) . . . . ? C2 C1 C6 C7 173.3(4) . . . . ? C8 C7 C6 C5 -174.3(4) . . . . ? C14 C7 C6 C5 -58.2(6) . . . . ? C8 C7 C6 C1 11.1(4) . . . . ? C14 C7 C6 C1 127.1(4) . . . . ? C28 C22 C23 C24 0.9(7) . . . . ? S1 C22 C23 C24 -175.0(4) . . . . ? C1 N1 C8 C9 -99.8(5) . . . . ? C1 N1 C8 C7 13.4(5) . . . . ? C6 C7 C8 N1 -14.3(4) . . . . ? C14 C7 C8 N1 -138.7(3) . . . . ? C6 C7 C8 C9 106.0(3) . . . . ? C14 C7 C8 C9 -18.4(4) . . . . ? C14 C13 C9 C10 -174.7(4) . . . . ? S1 C13 C9 C10 4.6(7) . . . . ? C14 C13 C9 C8 3.2(5) . . . . ? S1 C13 C9 C8 -177.5(3) . . . . ? N1 C8 C9 C13 123.6(4) . . . . ? C7 C8 C9 C13 9.9(5) . . . . ? N1 C8 C9 C10 -58.1(5) . . . . ? C7 C8 C9 C10 -171.9(4) . . . . ? C22 C28 C27 C25 -0.5(7) . . . . ? C28 C27 C25 C24 2.5(6) . . . . ? C28 C27 C25 C26 -176.4(4) . . . . ? N1 C1 C2 C3 178.3(5) . . . . ? C6 C1 C2 C3 2.2(7) . . . . ? C1 C2 C3 C4 -0.8(7) . . . . ? C16 C15 C21 C20 -3.7(6) . . . . ? C14 C15 C21 C20 177.8(4) . . . . ? C18 C20 C21 C15 2.2(6) . . . . ? C13 C9 C10 C11 -87.9(6) . . . . ? C8 C9 C10 C11 94.3(6) . . . . ? C13 C9 C10 C12 97.8(6) . . . . ? C8 C9 C10 C12 -80.0(6) . . . . ? C22 C23 C24 C25 1.1(7) . . . . ? C27 C25 C24 C23 -2.8(7) . . . . ? C26 C25 C24 C23 176.0(4) . . . . ? C2 C3 C4 C5 -0.8(8) . . . . ? C6 C5 C4 C3 0.9(7) . . . . ?