#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:02:08 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247579 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125666.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_7125666 loop_ _publ_author_name 'Kahar, Nilesh' 'Jadhav, Pankaj' 'Reddy, R. V. Ramana' 'Dawande, Sudam' _publ_section_title ; A rhodium(ii) catalysed domino synthesis of azepino fused diindoles from isatin tethered N-sulfonyl-1,2,3-triazoles and indoles. ; _journal_issue 8 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 1207 _journal_page_last 1210 _journal_paper_doi 10.1039/c9cc08377d _journal_volume 56 _journal_year 2020 _chemical_formula_sum 'C29 H23 N3 O4 S' _chemical_formula_weight 509.56 _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 _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2019-04-21 deposited with the CCDC. 2019-12-17 downloaded from the CCDC. ; _cell_angle_alpha 106.799(4) _cell_angle_beta 100.940(4) _cell_angle_gamma 116.237(4) _cell_formula_units_Z 2 _cell_length_a 10.8543(11) _cell_length_b 11.7730(11) _cell_length_c 11.9282(10) _cell_measurement_reflns_used 3079 _cell_measurement_temperature 282(2) _cell_measurement_theta_max 22.75 _cell_measurement_theta_min 2.25 _cell_volume 1216.1(2) _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-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 282(2) _diffrn_measured_fraction_theta_full 0.995 _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 0.1709 _diffrn_reflns_av_unetI/netI 0.1455 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 17413 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.177 _diffrn_reflns_theta_max 25.177 _diffrn_reflns_theta_min 2.251 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6563 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2014/5' _exptl_crystal_colour black _exptl_crystal_density_diffrn 1.392 _exptl_crystal_description block _exptl_crystal_F_000 532 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.175 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.354 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.061 _refine_ls_extinction_coef 0.012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)' _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 336 _refine_ls_number_reflns 4336 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.016 _refine_ls_R_factor_all 0.1673 _refine_ls_R_factor_gt 0.0725 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.3703P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1299 _refine_ls_wR_factor_ref 0.1617 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2258 _reflns_number_total 4336 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc08377d2.cif _cod_data_source_block shelx _cod_depositor_comments 'Adding full bibliography for 7125665--7125666.cif.' _cod_database_code 7125666 _shelx_shelxl_version_number 2017/1 _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 ; CELL 0.71073 10.8543 11.7730 11.9282 106.799 100.940 116.237 ZERR 2.00 0.0011 0.0011 0.0010 0.004 0.004 0.004 LATT 1 SFAC C H N O S UNIT 58 46 6 8 2 L.S. 15 ACTA BOND $H FMAP 2 PLAN 4 HTAB C27 N1 HTAB C27 S1 HTAB C21 O1_$1 HTAB N1 O2_$2 HTAB C27 N1 HTAB C27 S1 HTAB C21 O1_$1 HTAB N1 O2_$2 HTAB C25 N1 HTAB C25 S1 HTAB C10 O2_$1 HTAB N1 O1_$2 HTAB CONF EQIV $1 -x+2, -y+1, -z+2 HTAB C10 O2_$1 HTAB C25 S1 HTAB C25 N1 EQIV $2 -x+1, -y+1, -z+1 HTAB N1 O1_$2 HTAB C10 O2_$1 HTAB C25 S1 HTAB C25 N1 HTAB N1 O1_$2 HTAB C10 O2_$1 HTAB C25 S1 HTAB C25 N1 HTAB N1 O1_$2 HTAB C10 O2_$1 HTAB C25 S1 HTAB C25 N1 HTAB N1 O2_$2 HTAB C21 O1_$1 HTAB C27 S1 HTAB C27 N1 TEMP 9.310 WGHT 0.061600 0.370300 EXTI 0.011917 FVAR 0.16342 S1 5 0.838499 0.716561 0.683957 11.00000 0.03722 0.03139 = 0.02319 0.00904 0.00963 0.01486 O2 4 0.493855 0.382166 0.558856 11.00000 0.04629 0.04473 = 0.02764 0.01340 -0.00079 0.01911 O1 4 0.908157 0.457650 1.092984 11.00000 0.06987 0.05621 = 0.03525 0.01024 -0.00288 0.03979 O3 4 0.945419 0.779712 0.808469 11.00000 0.03915 0.04322 = 0.02672 0.00393 -0.00044 0.01117 O4 4 0.847922 0.798084 0.613810 11.00000 0.06212 0.03540 = 0.03698 0.02223 0.02314 0.02050 N1 3 0.676350 0.661452 0.697481 11.00000 0.03676 0.03658 = 0.03148 0.01901 0.01280 0.02741 AFIX 43 H35 2 0.618023 0.686724 0.670191 11.00000 -1.20000 AFIX 0 N2 3 0.739060 0.756865 0.971589 11.00000 0.05397 0.02968 = 0.02580 0.01731 0.01944 0.02585 N3 3 0.638117 0.334119 0.803901 11.00000 0.03641 0.02383 = 0.01963 0.00323 -0.00004 0.01431 C1 1 0.803133 0.075041 0.773010 11.00000 0.07044 0.04903 = 0.06961 0.03066 0.03575 0.04472 AFIX 43 H1 2 0.845238 0.020931 0.768840 11.00000 -1.20000 AFIX 0 C2 1 0.853893 0.189378 0.883291 11.00000 0.04584 0.04250 = 0.05199 0.02459 0.01738 0.02928 AFIX 43 H11 2 0.927827 0.212010 0.954973 11.00000 -1.20000 AFIX 0 C3 1 0.791664 0.269530 0.884271 11.00000 0.04010 0.03353 = 0.03434 0.01355 0.01096 0.02349 C7 1 0.819256 0.394702 0.985208 11.00000 0.03455 0.03850 = 0.03148 0.01904 0.00989 0.01834 C8 1 0.719651 0.434194 0.924597 11.00000 0.03634 0.02657 = 0.02580 0.01486 0.01091 0.01521 C9 1 0.718894 0.555422 0.968960 11.00000 0.02898 0.02715 = 0.02184 0.01123 0.00648 0.01514 C16 1 0.689135 0.621731 0.889634 11.00000 0.03010 0.02603 = 0.02432 0.00795 0.00958 0.01600 C17 1 0.638783 0.568622 0.757701 11.00000 0.03425 0.02906 = 0.02506 0.01535 0.01180 0.01846 C20 1 0.833237 0.566105 0.594919 11.00000 0.03401 0.03535 = 0.03249 0.01205 0.01195 0.01768 C21 1 0.886167 0.503145 0.652709 11.00000 0.04192 0.05528 = 0.04898 0.02279 0.01476 0.02811 AFIX 43 H6 2 0.933826 0.545236 0.739839 11.00000 -1.20000 AFIX 0 C22 1 0.869420 0.379119 0.583280 11.00000 0.06147 0.05468 = 0.07892 0.03005 0.02973 0.04074 AFIX 43 H5 2 0.905026 0.337371 0.624252 11.00000 -1.20000 AFIX 0 C23 1 0.801823 0.314938 0.455420 11.00000 0.05266 0.04120 = 0.07667 0.01646 0.03487 0.02875 C26 1 0.779597 0.176111 0.375526 11.00000 0.09338 0.05251 = 0.14307 0.01992 0.06256 0.04522 AFIX 137 H2 2 0.824016 0.186508 0.313927 11.00000 -1.50000 H4 2 0.675736 0.107308 0.333587 11.00000 -1.50000 H3 2 0.824974 0.146666 0.428508 11.00000 -1.50000 AFIX 0 C15 1 0.786998 0.775356 1.095747 11.00000 0.03661 0.03067 = 0.02255 0.01119 0.01223 0.01906 C10 1 0.777239 0.655002 1.098498 11.00000 0.04005 0.03607 = 0.02036 0.01326 0.01313 0.02211 C4 1 0.690703 0.040252 0.669027 11.00000 0.08170 0.04538 = 0.04809 0.00948 0.01936 0.03961 AFIX 43 H10 2 0.656642 -0.038880 0.596208 11.00000 -1.20000 AFIX 0 C5 1 0.625912 0.119130 0.668692 11.00000 0.06600 0.04140 = 0.03484 0.00665 0.00601 0.03101 AFIX 43 H9 2 0.549886 0.094641 0.597670 11.00000 -1.20000 AFIX 0 C6 1 0.679586 0.234680 0.778129 11.00000 0.04161 0.03279 = 0.03227 0.01287 0.01389 0.02510 C19 1 0.504293 0.318411 0.729374 11.00000 0.03149 0.03143 = 0.03113 0.00562 -0.00046 0.01486 AFIX 23 H8 2 0.450170 0.333037 0.782312 11.00000 -1.20000 H7 2 0.441469 0.224440 0.662590 11.00000 -1.20000 AFIX 0 C18 1 0.543666 0.422690 0.673414 11.00000 0.02885 0.04007 = 0.02414 0.01488 0.00435 0.02152 C11 1 0.815251 0.649432 1.214886 11.00000 0.04979 0.03829 = 0.02856 0.01689 0.01548 0.02562 AFIX 43 H12 2 0.807035 0.568850 1.219094 11.00000 -1.20000 AFIX 0 C12 1 0.865034 0.765999 1.322843 11.00000 0.05557 0.04879 = 0.02279 0.01374 0.01298 0.02458 AFIX 43 H15 2 0.890785 0.763598 1.400694 11.00000 -1.20000 AFIX 0 C13 1 0.877751 0.886834 1.318458 11.00000 0.04715 0.03431 = 0.02133 -0.00018 0.00641 0.01359 AFIX 43 H13 2 0.913535 0.964520 1.393167 11.00000 -1.20000 AFIX 0 C14 1 0.837978 0.893408 1.204585 11.00000 0.04834 0.02587 = 0.03427 0.01055 0.01491 0.01731 AFIX 43 H14 2 0.845054 0.973812 1.200904 11.00000 -1.20000 AFIX 0 C27 1 0.729540 0.865461 0.943230 11.00000 0.08449 0.04027 = 0.03287 0.01866 0.02639 0.04232 AFIX 23 H16 2 0.733436 0.852957 0.860225 11.00000 -1.20000 H19 2 0.815650 0.955386 1.003418 11.00000 -1.20000 AFIX 0 C28 1 0.596876 0.869042 0.945847 11.00000 0.10928 0.10661 = 0.10191 0.06172 0.05196 0.08803 AFIX 43 H17 2 0.592747 0.940157 0.929532 11.00000 -1.20000 AFIX 0 C29 1 0.493900 0.796144 0.965356 11.00000 0.08899 0.19408 = 0.16893 0.13490 0.08248 0.08164 AFIX 93 H27A 2 0.489633 0.722544 0.982463 11.00000 -1.20000 H27B 2 0.417402 0.812570 0.963549 11.00000 -1.20000 AFIX 0 C25 1 0.762435 0.502649 0.465454 11.00000 0.06047 0.04593 = 0.03421 0.01482 0.01600 0.03141 AFIX 43 H21 2 0.724632 0.543567 0.425182 11.00000 -1.20000 AFIX 0 C24 1 0.748250 0.378992 0.396721 11.00000 0.06568 0.05031 = 0.04671 0.00205 0.02124 0.02552 AFIX 43 H20 2 0.702070 0.337249 0.309447 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM REM R1 = 0.0725 for 2258 Fo > 4sig(Fo) and 0.1673 for all 4336 data REM 336 parameters refined using 0 restraints END WGHT 0.0544 0.5689 REM Instructions for potential hydrogen bonds HTAB N1 O2_$2 HTAB C21 O1_$1 HTAB C27 S1 HTAB C27 N1 REM Highest difference peak 0.354, deepest hole -0.424, 1-sigma level 0.061 Q1 1 0.5849 0.6032 0.5983 11.00000 0.05 0.35 Q2 1 0.5627 0.9382 1.0497 11.00000 0.05 0.32 Q3 1 0.8180 0.6232 0.6269 11.00000 0.05 0.25 Q4 1 0.6994 0.2213 0.7134 11.00000 0.05 0.23 ; _shelx_res_checksum 26002 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 0.83850(12) 0.71656(12) 0.68396(10) 0.0330(3) Uani 1 1 d . . O2 O 0.4939(3) 0.3822(3) 0.5589(3) 0.0447(9) Uani 1 1 d . . O1 O 0.9082(4) 0.4576(4) 1.0930(3) 0.0572(10) Uani 1 1 d . . O3 O 0.9454(3) 0.7797(3) 0.8085(3) 0.0460(9) Uani 1 1 d . . O4 O 0.8479(3) 0.7981(3) 0.6138(3) 0.0445(9) Uani 1 1 d . . N1 N 0.6764(4) 0.6615(3) 0.6975(3) 0.0302(9) Uani 1 1 d . . H35 H 0.618023 0.686724 0.670191 0.036 Uiso 1 1 calc R U N2 N 0.7391(4) 0.7569(4) 0.9716(3) 0.0326(9) Uani 1 1 d . . N3 N 0.6381(4) 0.3341(3) 0.8039(3) 0.0307(9) Uani 1 1 d . . C1 C 0.8031(6) 0.0750(5) 0.7730(5) 0.0541(14) Uani 1 1 d . . H1 H 0.845238 0.020931 0.768840 0.065 Uiso 1 1 calc R U C2 C 0.8539(5) 0.1894(5) 0.8833(4) 0.0431(12) Uani 1 1 d . . H11 H 0.927827 0.212010 0.954973 0.052 Uiso 1 1 calc R U C3 C 0.7917(5) 0.2695(5) 0.8843(4) 0.0349(11) Uani 1 1 d . . C7 C 0.8193(5) 0.3947(5) 0.9852(4) 0.0345(11) Uani 1 1 d . . C8 C 0.7197(4) 0.4342(4) 0.9246(4) 0.0293(10) Uani 1 1 d . . C9 C 0.7189(4) 0.5554(4) 0.9690(3) 0.0261(10) Uani 1 1 d . . C16 C 0.6891(4) 0.6217(4) 0.8896(4) 0.0271(10) Uani 1 1 d . . C17 C 0.6388(4) 0.5686(4) 0.7577(4) 0.0275(10) Uani 1 1 d . . C20 C 0.8332(5) 0.5661(5) 0.5949(4) 0.0349(11) Uani 1 1 d . . C21 C 0.8862(5) 0.5031(5) 0.6527(5) 0.0478(13) Uani 1 1 d . . H6 H 0.933826 0.545236 0.739839 0.057 Uiso 1 1 calc R U C22 C 0.8694(6) 0.3791(6) 0.5833(6) 0.0595(15) Uani 1 1 d . . H5 H 0.905026 0.337371 0.624252 0.071 Uiso 1 1 calc R U C23 C 0.8018(6) 0.3149(5) 0.4554(6) 0.0555(15) Uani 1 1 d . . C26 C 0.7796(7) 0.1761(6) 0.3755(6) 0.096(2) Uani 1 1 d . . H2 H 0.824016 0.186508 0.313927 0.144 Uiso 1 1 calc R U H4 H 0.675736 0.107308 0.333587 0.144 Uiso 1 1 calc R U H3 H 0.824974 0.146666 0.428508 0.144 Uiso 1 1 calc R U C15 C 0.7870(4) 0.7754(4) 1.0957(4) 0.0292(10) Uani 1 1 d . . C10 C 0.7772(5) 0.6550(5) 1.0985(4) 0.0306(11) Uani 1 1 d . . C4 C 0.6907(6) 0.0403(5) 0.6690(5) 0.0593(15) Uani 1 1 d . . H10 H 0.656642 -0.038880 0.596208 0.071 Uiso 1 1 calc R U C5 C 0.6259(6) 0.1191(5) 0.6687(4) 0.0510(14) Uani 1 1 d . . H9 H 0.549886 0.094641 0.597670 0.061 Uiso 1 1 calc R U C6 C 0.6796(5) 0.2347(5) 0.7781(4) 0.0334(11) Uani 1 1 d . . C19 C 0.5043(4) 0.3184(5) 0.7294(4) 0.0362(11) Uani 1 1 d . . H8 H 0.450170 0.333037 0.782312 0.043 Uiso 1 1 calc R U H7 H 0.441469 0.224440 0.662590 0.043 Uiso 1 1 calc R U C18 C 0.5437(4) 0.4227(5) 0.6734(4) 0.0302(11) Uani 1 1 d . . C11 C 0.8153(5) 0.6494(5) 1.2149(4) 0.0370(11) Uani 1 1 d . . H12 H 0.807035 0.568850 1.219094 0.044 Uiso 1 1 calc R U C12 C 0.8650(5) 0.7660(5) 1.3228(4) 0.0443(13) Uani 1 1 d . . H15 H 0.890785 0.763598 1.400694 0.053 Uiso 1 1 calc R U C13 C 0.8778(5) 0.8868(5) 1.3185(4) 0.0420(12) Uani 1 1 d . . H13 H 0.913535 0.964520 1.393167 0.050 Uiso 1 1 calc R U C14 C 0.8380(5) 0.8934(5) 1.2046(4) 0.0378(12) Uani 1 1 d . . H14 H 0.845054 0.973812 1.200904 0.045 Uiso 1 1 calc R U C27 C 0.7295(6) 0.8655(5) 0.9432(4) 0.0468(13) Uani 1 1 d . . H16 H 0.733436 0.852957 0.860225 0.056 Uiso 1 1 calc R U H19 H 0.815650 0.955386 1.003418 0.056 Uiso 1 1 calc R U C28 C 0.5969(8) 0.8690(8) 0.9458(6) 0.086(2) Uani 1 1 d . . H17 H 0.592747 0.940157 0.929532 0.103 Uiso 1 1 calc R U C29 C 0.4939(8) 0.7961(9) 0.9654(7) 0.126(3) Uani 1 1 d . . H27A H 0.489633 0.722544 0.982463 0.152 Uiso 1 1 calc R U H27B H 0.417402 0.812570 0.963549 0.152 Uiso 1 1 calc R U C25 C 0.7624(5) 0.5026(5) 0.4655(4) 0.0463(13) Uani 1 1 d . . H21 H 0.724632 0.543567 0.425182 0.056 Uiso 1 1 calc R U C24 C 0.7482(6) 0.3790(6) 0.3967(5) 0.0613(16) Uani 1 1 d . . H20 H 0.702070 0.337249 0.309447 0.074 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 0.0372(7) 0.0314(7) 0.0232(6) 0.0090(6) 0.0096(6) 0.0149(6) O2 0.046(2) 0.045(2) 0.0276(18) 0.0134(16) -0.0008(16) 0.0191(18) O1 0.070(2) 0.056(2) 0.035(2) 0.0102(18) -0.0029(19) 0.040(2) O3 0.0392(18) 0.043(2) 0.0267(17) 0.0039(15) -0.0004(15) 0.0112(17) O4 0.062(2) 0.035(2) 0.0370(18) 0.0222(16) 0.0231(17) 0.0205(18) N1 0.037(2) 0.037(2) 0.031(2) 0.0190(18) 0.0128(17) 0.0274(19) N2 0.054(2) 0.030(2) 0.026(2) 0.0173(18) 0.0194(18) 0.026(2) N3 0.036(2) 0.024(2) 0.0196(19) 0.0032(17) 0.0000(17) 0.0143(19) C1 0.070(4) 0.049(4) 0.070(4) 0.031(3) 0.036(3) 0.045(3) C2 0.046(3) 0.042(3) 0.052(3) 0.025(3) 0.017(3) 0.029(3) C3 0.040(3) 0.034(3) 0.034(3) 0.014(2) 0.011(2) 0.023(2) C7 0.035(3) 0.038(3) 0.031(3) 0.019(2) 0.010(2) 0.018(2) C8 0.036(3) 0.027(3) 0.026(2) 0.015(2) 0.011(2) 0.015(2) C9 0.029(2) 0.027(3) 0.022(2) 0.011(2) 0.006(2) 0.015(2) C16 0.030(2) 0.026(3) 0.024(2) 0.008(2) 0.010(2) 0.016(2) C17 0.034(3) 0.029(3) 0.025(2) 0.015(2) 0.012(2) 0.018(2) C20 0.034(3) 0.035(3) 0.032(3) 0.012(2) 0.012(2) 0.018(2) C21 0.042(3) 0.055(4) 0.049(3) 0.023(3) 0.015(3) 0.028(3) C22 0.061(4) 0.055(4) 0.079(4) 0.030(3) 0.030(3) 0.041(3) C23 0.053(3) 0.041(3) 0.077(4) 0.016(3) 0.035(3) 0.029(3) C26 0.093(5) 0.053(4) 0.143(6) 0.020(4) 0.063(5) 0.045(4) C15 0.037(3) 0.031(3) 0.023(2) 0.011(2) 0.012(2) 0.019(2) C10 0.040(3) 0.036(3) 0.020(2) 0.013(2) 0.013(2) 0.022(2) C4 0.082(4) 0.045(4) 0.048(3) 0.009(3) 0.019(3) 0.040(3) C5 0.066(4) 0.041(3) 0.035(3) 0.007(3) 0.006(3) 0.031(3) C6 0.042(3) 0.033(3) 0.032(3) 0.013(2) 0.014(2) 0.025(2) C19 0.031(3) 0.031(3) 0.031(3) 0.006(2) 0.000(2) 0.015(2) C18 0.029(2) 0.040(3) 0.024(3) 0.015(2) 0.004(2) 0.022(2) C11 0.050(3) 0.038(3) 0.029(3) 0.017(2) 0.015(2) 0.026(3) C12 0.056(3) 0.049(4) 0.023(3) 0.014(2) 0.013(2) 0.025(3) C13 0.047(3) 0.034(3) 0.021(3) 0.000(2) 0.006(2) 0.014(3) C14 0.048(3) 0.026(3) 0.034(3) 0.011(2) 0.015(2) 0.017(2) C27 0.084(4) 0.040(3) 0.033(3) 0.019(2) 0.026(3) 0.042(3) C28 0.109(6) 0.107(6) 0.102(5) 0.062(5) 0.052(5) 0.088(5) C29 0.089(6) 0.194(10) 0.169(8) 0.135(7) 0.082(6) 0.082(6) C25 0.060(3) 0.046(3) 0.034(3) 0.015(3) 0.016(3) 0.031(3) C24 0.066(4) 0.050(4) 0.047(3) 0.002(3) 0.021(3) 0.026(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 O4 S1 O3 119.7(2) O4 S1 N1 105.96(18) O3 S1 N1 106.53(17) O4 S1 C20 109.49(19) O3 S1 C20 108.5(2) N1 S1 C20 105.83(19) C17 N1 S1 115.5(3) C17 N1 H35 122.2 S1 N1 H35 122.2 C16 N2 C15 110.3(3) C16 N2 C27 128.8(3) C15 N2 C27 120.4(3) C8 N3 C6 110.8(3) C8 N3 C19 121.3(3) C6 N3 C19 126.1(3) C4 C1 C2 120.4(4) C4 C1 H1 119.8 C2 C1 H1 119.8 C1 C2 C3 117.9(4) C1 C2 H11 121.0 C3 C2 H11 121.0 C2 C3 C6 121.2(4) C2 C3 C7 131.3(4) C6 C3 C7 107.5(4) O1 C7 C3 128.1(4) O1 C7 C8 126.8(4) C3 C7 C8 104.9(4) N3 C8 C9 123.0(4) N3 C8 C7 107.0(4) C9 C8 C7 129.3(4) C8 C9 C10 127.6(4) C8 C9 C16 123.9(3) C10 C9 C16 107.1(3) N2 C16 C17 125.6(4) N2 C16 C9 105.9(3) C17 C16 C9 128.1(4) C16 C17 N1 120.4(4) C16 C17 C18 124.6(4) N1 C17 C18 115.0(3) C21 C20 C25 119.3(4) C21 C20 S1 120.8(3) C25 C20 S1 119.6(4) C22 C21 C20 120.4(5) C22 C21 H6 119.8 C20 C21 H6 119.8 C21 C22 C23 121.6(5) C21 C22 H5 119.2 C23 C22 H5 119.2 C22 C23 C24 118.0(5) C22 C23 C26 123.0(6) C24 C23 C26 119.1(5) C23 C26 H2 109.5 C23 C26 H4 109.5 H2 C26 H4 109.5 C23 C26 H3 109.5 H2 C26 H3 109.5 H4 C26 H3 109.5 C10 C15 C14 122.5(4) C10 C15 N2 109.8(3) C14 C15 N2 127.7(4) C15 C10 C11 119.2(4) C15 C10 C9 106.8(3) C11 C10 C9 134.0(4) C1 C4 C5 122.4(5) C1 C4 H10 118.8 C5 C4 H10 118.8 C6 C5 C4 116.7(5) C6 C5 H9 121.6 C4 C5 H9 121.6 C5 C6 C3 121.3(4) C5 C6 N3 129.1(4) C3 C6 N3 109.6(3) N3 C19 C18 109.7(3) N3 C19 H8 109.7 C18 C19 H8 109.7 N3 C19 H7 109.7 C18 C19 H7 109.7 H8 C19 H7 108.2 O2 C18 C17 122.1(4) O2 C18 C19 119.8(4) C17 C18 C19 118.2(4) C12 C11 C10 118.4(4) C12 C11 H12 120.8 C10 C11 H12 120.8 C11 C12 C13 121.6(4) C11 C12 H15 119.2 C13 C12 H15 119.2 C14 C13 C12 120.8(4) C14 C13 H13 119.6 C12 C13 H13 119.6 C13 C14 C15 117.4(4) C13 C14 H14 121.3 C15 C14 H14 121.3 N2 C27 C28 115.3(5) N2 C27 H16 108.5 C28 C27 H16 108.5 N2 C27 H19 108.5 C28 C27 H19 108.5 H16 C27 H19 107.5 C29 C28 C27 130.6(7) C29 C28 H17 114.7 C27 C28 H17 114.7 C28 C29 H27A 120.0 C28 C29 H27B 120.0 H27A C29 H27B 120.0 C24 C25 C20 119.6(5) C24 C25 H21 120.2 C20 C25 H21 120.2 C25 C24 C23 121.1(5) C25 C24 H20 119.5 C23 C24 H20 119.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O4 1.429(3) S1 O3 1.432(3) S1 N1 1.644(3) S1 C20 1.752(4) O2 C18 1.226(4) O1 C7 1.216(5) N1 C17 1.431(5) N1 H35 0.8600 N2 C16 1.385(5) N2 C15 1.390(5) N2 C27 1.454(5) N3 C8 1.363(5) N3 C6 1.406(5) N3 C19 1.453(5) C1 C4 1.373(6) C1 C2 1.375(6) C1 H1 0.9300 C2 C3 1.381(6) C2 H11 0.9300 C3 C6 1.387(5) C3 C7 1.469(6) C7 C8 1.500(6) C8 C9 1.376(5) C9 C10 1.445(5) C9 C16 1.464(5) C16 C17 1.403(5) C17 C18 1.438(6) C20 C21 1.370(6) C20 C25 1.382(6) C21 C22 1.364(6) C21 H6 0.9300 C22 C23 1.362(7) C22 H5 0.9300 C23 C24 1.391(7) C23 C26 1.517(7) C26 H2 0.9600 C26 H4 0.9600 C26 H3 0.9600 C15 C10 1.384(6) C15 C14 1.388(5) C10 C11 1.400(5) C4 C5 1.391(6) C4 H10 0.9300 C5 C6 1.370(6) C5 H9 0.9300 C19 C18 1.501(6) C19 H8 0.9700 C19 H7 0.9700 C11 C12 1.376(6) C11 H12 0.9300 C12 C13 1.385(6) C12 H15 0.9300 C13 C14 1.380(6) C13 H13 0.9300 C14 H14 0.9300 C27 C28 1.465(7) C27 H16 0.9700 C27 H19 0.9700 C28 C29 1.186(8) C28 H17 0.9300 C29 H27A 0.9300 C29 H27B 0.9300 C25 C24 1.371(6) C25 H21 0.9300 C24 H20 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C27 H16 N1 0.97 2.24 2.959(5) 130.2 . yes C27 H16 S1 0.97 2.98 3.758(4) 138.1 . yes C21 H6 O1 0.93 2.39 3.179(6) 142.6 2_767 yes N1 H35 O2 0.86 2.49 3.022(4) 121.1 2_666 yes C27 H16 N1 0.97 2.24 2.959(5) 130.2 . yes C27 H16 S1 0.97 2.98 3.758(4) 138.1 . yes C21 H6 O1 0.93 2.39 3.179(6) 142.6 2_767 yes N1 H35 O2 0.86 2.49 3.022(4) 121.1 2_666 yes N1 H35 O2 0.86 2.49 3.022(4) 121.1 2_666 yes C21 H6 O1 0.93 2.39 3.179(6) 142.6 2_767 yes C27 H16 S1 0.97 2.98 3.758(4) 138.1 . yes C27 H16 N1 0.97 2.24 2.959(5) 130.2 . yes 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 O4 S1 N1 C17 175.8(3) O3 S1 N1 C17 -55.7(3) C20 S1 N1 C17 59.6(3) C4 C1 C2 C3 -2.1(7) C1 C2 C3 C6 1.1(7) C1 C2 C3 C7 179.1(5) C2 C3 C7 O1 1.3(8) C6 C3 C7 O1 179.5(4) C2 C3 C7 C8 178.1(5) C6 C3 C7 C8 -3.7(5) C6 N3 C8 C9 169.5(4) C19 N3 C8 C9 -25.0(6) C6 N3 C8 C7 -2.3(5) C19 N3 C8 C7 163.2(4) O1 C7 C8 N3 -179.5(4) C3 C7 C8 N3 3.7(4) O1 C7 C8 C9 9.4(7) C3 C7 C8 C9 -167.4(4) N3 C8 C9 C10 167.3(4) C7 C8 C9 C10 -22.9(7) N3 C8 C9 C16 -27.8(6) C7 C8 C9 C16 142.0(4) C15 N2 C16 C17 -177.1(4) C27 N2 C16 C17 10.9(7) C15 N2 C16 C9 -4.5(4) C27 N2 C16 C9 -176.5(4) C8 C9 C16 N2 -163.4(4) C10 C9 C16 N2 4.1(4) C8 C9 C16 C17 9.0(7) C10 C9 C16 C17 176.5(4) N2 C16 C17 N1 19.2(6) C9 C16 C17 N1 -151.8(4) N2 C16 C17 C18 -158.1(4) C9 C16 C17 C18 30.9(6) S1 N1 C17 C16 83.7(4) S1 N1 C17 C18 -98.7(4) O4 S1 C20 C21 151.9(4) O3 S1 C20 C21 19.7(4) N1 S1 C20 C21 -94.3(4) O4 S1 C20 C25 -34.3(4) O3 S1 C20 C25 -166.5(3) N1 S1 C20 C25 79.5(4) C25 C20 C21 C22 0.1(7) S1 C20 C21 C22 173.9(4) C20 C21 C22 C23 0.8(8) C21 C22 C23 C24 -0.7(8) C21 C22 C23 C26 -179.2(5) C16 N2 C15 C10 3.2(5) C27 N2 C15 C10 176.0(4) C16 N2 C15 C14 -176.7(4) C27 N2 C15 C14 -3.9(6) C14 C15 C10 C11 2.2(6) N2 C15 C10 C11 -177.7(4) C14 C15 C10 C9 179.4(4) N2 C15 C10 C9 -0.5(5) C8 C9 C10 C15 164.7(4) C16 C9 C10 C15 -2.3(4) C8 C9 C10 C11 -18.7(8) C16 C9 C10 C11 174.4(4) C2 C1 C4 C5 1.6(8) C1 C4 C5 C6 -0.1(8) C4 C5 C6 C3 -0.9(7) C4 C5 C6 N3 178.4(4) C2 C3 C6 C5 0.4(7) C7 C3 C6 C5 -178.1(4) C2 C3 C6 N3 -179.1(4) C7 C3 C6 N3 2.5(5) C8 N3 C6 C5 -179.5(4) C19 N3 C6 C5 15.9(7) C8 N3 C6 C3 -0.1(5) C19 N3 C6 C3 -164.7(4) C8 N3 C19 C18 81.9(5) C6 N3 C19 C18 -115.0(4) C16 C17 C18 O2 174.5(4) N1 C17 C18 O2 -3.0(6) C16 C17 C18 C19 -4.9(6) N1 C17 C18 C19 177.6(3) N3 C19 C18 O2 122.2(4) N3 C19 C18 C17 -58.4(5) C15 C10 C11 C12 -1.8(6) C9 C10 C11 C12 -178.1(4) C10 C11 C12 C13 0.1(7) C11 C12 C13 C14 1.2(7) C12 C13 C14 C15 -0.8(6) C10 C15 C14 C13 -0.9(6) N2 C15 C14 C13 179.0(4) C16 N2 C27 C28 90.6(5) C15 N2 C27 C28 -80.7(6) N2 C27 C28 C29 -1.4(11) C21 C20 C25 C24 -1.0(7) S1 C20 C25 C24 -174.9(4) C20 C25 C24 C23 1.1(8) C22 C23 C24 C25 -0.3(8) C26 C23 C24 C25 178.3(5)