#------------------------------------------------------------------------------ #$Date: 2017-06-16 07:59:25 +0300 (Fri, 16 Jun 2017) $ #$Revision: 197884 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/85/7228503.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_7228503 loop_ _publ_author_name 'Pess\^ego, M\'arcia' 'Bas\'ilio, Nuno' 'Mendoza, Johan' 'Av\'o, Jo\~ao' 'Cunha-Silva, Lu\'is' 'Parola, A. Jorge' 'Pina, Fernando' _publ_section_title ; Exploring the diethylaminoflavylium derivatives multistate system of chemical reactions in the presence of CTAB micelles: thermodynamic reversibility achieved through different kinetic pathways ; _journal_issue 48 _journal_name_full 'RSC Adv.' _journal_page_first 30469 _journal_paper_doi 10.1039/C7RA04514J _journal_volume 7 _journal_year 2017 _chemical_formula_moiety 'C21 H22 N O2, H O4 S' _chemical_formula_sum 'C21 H23 N O6 S' _chemical_formula_weight 417.46 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_date '10 February 2017' _audit_creation_method 'SHELXL-2014/7 and enCIFer' _audit_update_record ; 2017-04-10 deposited with the CCDC. 2017-05-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 114.240(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.3956(7) _cell_length_b 14.0481(9) _cell_length_c 13.0280(8) _cell_measurement_reflns_used 9991 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 29.01 _cell_measurement_theta_min 2.47 _cell_volume 1901.7(2) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker X8 Kappa CCD APEX II' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_unetI/netI 0.0170 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 50030 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.678 _diffrn_reflns_theta_min 3.724 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_correction_T_min 0.929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; 'SADABS V2012/1 (Bruker AXS Inc.)' ; _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.458 _exptl_crystal_description block _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.070 _refine_diff_density_max 0.243 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 270 _refine_ls_number_reflns 3570 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0334 _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^)+(0.0438P)^2^+1.0668P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0870 _refine_ls_wR_factor_ref 0.0931 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3021 _reflns_number_total 3570 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ra04514j2.cif _cod_data_source_block comp2M _cod_database_code 7228503 _shelx_shelxl_version_number 2014/7 _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 0.930 _shelx_estimated_absorpt_t_max 0.985 _shelx_res_file ; lcs17001.res created by SHELXL-2014/7 TITL LCS17001.res in P2(1)/n CELL 0.71073 11.3956 14.0481 13.0280 90.000 114.240 90.000 ZERR 4.0000 0.0007 0.0009 0.0008 0.000 0.003 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 84 92 4 24 4 MERG 2 SHEL 5.60 0.82 FMAP 2 PLAN -5 TEMP -123 SIZE 0.07 0.17 0.35 BOND $H CONF WPDB DFIX 0.95 0.01 O1 H1 DFIX 0.95 0.01 O4 H4 EQIV $1 -x, -y+1, -z-1 HTAB O1 O3 HTAB O4 O5_$1 L.S. 50 ACTA WGHT 0.043800 1.066800 FVAR 0.29848 O1 4 -0.036582 0.630980 -0.084686 11.00000 0.02058 0.05208 = 0.01592 -0.00128 0.00132 0.00590 H1 2 -0.009768 0.626332 -0.142800 11.00000 -1.50000 O2 4 0.367323 0.632916 0.421628 11.00000 0.01491 0.02534 = 0.01236 0.00014 0.00453 -0.00003 N1 3 0.509080 0.665613 0.817952 11.00000 0.01825 0.02629 = 0.01426 -0.00152 0.00495 -0.00082 C1 1 0.068256 0.628530 0.014983 11.00000 0.02093 0.02373 = 0.01700 -0.00144 0.00265 0.00426 C2 1 0.048323 0.615520 0.113019 11.00000 0.01612 0.02885 = 0.02228 -0.00095 0.00585 0.00118 AFIX 43 H2 2 -0.036484 0.608132 0.108613 11.00000 -1.20000 AFIX 0 C3 1 0.152133 0.613453 0.216040 11.00000 0.02054 0.02291 = 0.01868 0.00032 0.00904 0.00067 AFIX 43 H3 2 0.138653 0.604802 0.282716 11.00000 -1.20000 AFIX 0 C4 1 0.277924 0.624072 0.223097 11.00000 0.01922 0.01585 = 0.01614 -0.00108 0.00606 -0.00068 C5 1 0.297735 0.637584 0.123754 11.00000 0.02193 0.01609 = 0.01811 -0.00108 0.00857 0.00098 C6 1 0.192394 0.639392 0.021014 11.00000 0.02475 0.02345 = 0.01670 0.00147 0.00859 0.00393 AFIX 43 H6 2 0.204871 0.648135 -0.046125 11.00000 -1.20000 AFIX 0 C7 1 0.432739 0.652622 0.133400 11.00000 0.02345 0.02733 = 0.01731 -0.00020 0.01030 -0.00278 AFIX 23 H7A 2 0.456357 0.720539 0.149379 11.00000 -1.20000 H7B 2 0.436743 0.636225 0.061003 11.00000 -1.20000 AFIX 0 C8 1 0.528323 0.591347 0.226921 11.00000 0.01778 0.02583 = 0.01925 -0.00347 0.00934 -0.00242 AFIX 23 H8A 2 0.513133 0.523358 0.205562 11.00000 -1.20000 H8B 2 0.617092 0.607517 0.237403 11.00000 -1.20000 AFIX 0 C9 1 0.513899 0.607479 0.335460 11.00000 0.01878 0.01687 = 0.01846 -0.00030 0.00794 -0.00161 C10 1 0.390279 0.621626 0.328231 11.00000 0.02116 0.01499 = 0.01675 0.00020 0.00925 -0.00191 C11 1 0.615158 0.605717 0.441001 11.00000 0.01673 0.01976 = 0.02390 -0.00037 0.00889 -0.00110 AFIX 43 H11 2 0.700122 0.594675 0.447361 11.00000 -1.20000 AFIX 0 C12 1 0.594073 0.619918 0.537916 11.00000 0.01690 0.01740 = 0.01988 0.00086 0.00669 -0.00064 C13 1 0.466386 0.632940 0.526998 11.00000 0.01663 0.01625 = 0.01591 0.00087 0.00367 -0.00144 C14 1 0.434323 0.647186 0.616532 11.00000 0.01504 0.02222 = 0.01756 0.00123 0.00652 0.00021 AFIX 43 H14 2 0.346859 0.653765 0.605134 11.00000 -1.20000 AFIX 0 C15 1 0.533963 0.651880 0.726040 11.00000 0.02025 0.01676 = 0.01684 -0.00016 0.00642 -0.00151 C16 1 0.664516 0.640070 0.738758 11.00000 0.01695 0.02595 = 0.01663 -0.00044 0.00241 -0.00202 AFIX 43 H16 2 0.732578 0.643818 0.811719 11.00000 -1.20000 AFIX 0 C17 1 0.692393 0.623714 0.648822 11.00000 0.01448 0.02543 = 0.02174 0.00049 0.00534 -0.00083 AFIX 43 H17 2 0.779456 0.614593 0.660120 11.00000 -1.20000 AFIX 0 C18 1 0.377910 0.658394 0.811605 11.00000 0.01942 0.02798 = 0.01594 0.00116 0.00722 0.00061 AFIX 23 H18A 2 0.380767 0.625272 0.879667 11.00000 -1.20000 H18B 2 0.325509 0.619195 0.745447 11.00000 -1.20000 AFIX 0 C19 1 0.313260 0.753797 0.802363 11.00000 0.03270 0.03402 = 0.05102 0.00801 0.02036 0.00934 AFIX 137 H19A 2 0.362837 0.792238 0.868919 11.00000 -1.50000 H19B 2 0.225943 0.744286 0.797522 11.00000 -1.50000 H19C 2 0.309048 0.786777 0.734650 11.00000 -1.50000 AFIX 0 C20 1 0.610730 0.684226 0.930675 11.00000 0.02233 0.02882 = 0.01569 -0.00565 0.00490 -0.00354 AFIX 23 H20A 2 0.575202 0.724793 0.973216 11.00000 -1.20000 H20B 2 0.681415 0.719895 0.922640 11.00000 -1.20000 AFIX 0 C21 1 0.664965 0.593941 0.997252 11.00000 0.02406 0.03690 = 0.01661 -0.00165 0.00291 0.00224 AFIX 137 H21A 2 0.594633 0.555976 1.000907 11.00000 -1.50000 H21B 2 0.725908 0.610611 1.073660 11.00000 -1.50000 H21C 2 0.709379 0.556929 0.960185 11.00000 -1.50000 AFIX 0 S1 5 0.043236 0.548333 -0.338701 11.00000 0.02069 0.02431 = 0.01976 0.00083 0.00776 0.00043 O3 4 0.019395 0.619500 -0.269006 11.00000 0.03614 0.03429 = 0.02227 -0.00405 0.01274 0.00023 O4 4 0.088059 0.608599 -0.417648 11.00000 0.04005 0.03159 = 0.02749 -0.00492 0.01892 -0.01065 H4 2 0.079442 0.570711 -0.479455 11.00000 -1.50000 O5 4 -0.076355 0.501137 -0.413750 11.00000 0.02739 0.04565 = 0.02759 -0.00926 0.01477 -0.01187 O6 4 0.143394 0.483138 -0.277451 11.00000 0.04180 0.03814 = 0.04632 0.01053 0.00724 0.01504 HKLF 4 REM LCS17001.res in P2(1)/n REM R1 = 0.0334 for 3021 Fo > 4sig(Fo) and 0.0422 for all 3570 data REM 270 parameters refined using 2 restraints END WGHT 0.0443 1.0763 REM Highest difference peak 0.243, deepest hole -0.436, 1-sigma level 0.048 Q1 1 0.1228 0.5509 -0.3838 11.00000 0.05 0.24 Q2 1 0.2848 0.6387 0.1743 11.00000 0.05 0.23 Q3 1 0.5255 0.6074 0.5280 11.00000 0.05 0.22 Q4 1 0.2204 0.6058 0.2157 11.00000 0.05 0.21 Q5 1 0.4517 0.6191 0.5787 11.00000 0.05 0.21 ; _shelx_res_checksum 97665 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp O1 O -0.03658(11) 0.63098(10) -0.08469(10) 0.0316(3) Uani 1 1 d D . H1 H -0.010(2) 0.6263(16) -0.1428(14) 0.047 Uiso 1 1 d D U O2 O 0.36732(10) 0.63292(8) 0.42163(9) 0.0179(2) Uani 1 1 d . . N1 N 0.50908(12) 0.66561(10) 0.81795(11) 0.0202(3) Uani 1 1 d . . C1 C 0.06826(15) 0.62853(12) 0.01498(14) 0.0222(4) Uani 1 1 d . . C2 C 0.04832(15) 0.61552(12) 0.11302(14) 0.0231(4) Uani 1 1 d . . H2 H -0.0365 0.6081 0.1086 0.028 Uiso 1 1 calc R U C3 C 0.15213(15) 0.61345(11) 0.21604(14) 0.0204(3) Uani 1 1 d . . H3 H 0.1387 0.6048 0.2827 0.024 Uiso 1 1 calc R U C4 C 0.27792(15) 0.62407(11) 0.22310(13) 0.0175(3) Uani 1 1 d . . C5 C 0.29774(15) 0.63758(11) 0.12375(13) 0.0186(3) Uani 1 1 d . . C6 C 0.19239(16) 0.63939(11) 0.02101(14) 0.0216(3) Uani 1 1 d . . H6 H 0.2049 0.6481 -0.0461 0.026 Uiso 1 1 calc R U C7 C 0.43274(15) 0.65262(12) 0.13340(13) 0.0221(4) Uani 1 1 d . . H7A H 0.4564 0.7205 0.1494 0.026 Uiso 1 1 calc R U H7B H 0.4367 0.6362 0.0610 0.026 Uiso 1 1 calc R U C8 C 0.52832(15) 0.59135(12) 0.22692(13) 0.0204(3) Uani 1 1 d . . H8A H 0.5131 0.5234 0.2056 0.024 Uiso 1 1 calc R U H8B H 0.6171 0.6075 0.2374 0.024 Uiso 1 1 calc R U C9 C 0.51390(15) 0.60748(11) 0.33546(13) 0.0179(3) Uani 1 1 d . . C10 C 0.39028(15) 0.62163(11) 0.32823(13) 0.0172(3) Uani 1 1 d . . C11 C 0.61516(15) 0.60572(11) 0.44100(14) 0.0199(3) Uani 1 1 d . . H11 H 0.7001 0.5947 0.4474 0.024 Uiso 1 1 calc R U C12 C 0.59407(15) 0.61992(11) 0.53792(13) 0.0183(3) Uani 1 1 d . . C13 C 0.46639(14) 0.63294(10) 0.52700(13) 0.0173(3) Uani 1 1 d . . C14 C 0.43432(14) 0.64719(11) 0.61653(13) 0.0183(3) Uani 1 1 d . . H14 H 0.3469 0.6538 0.6051 0.022 Uiso 1 1 calc R U C15 C 0.53396(15) 0.65188(11) 0.72604(13) 0.0183(3) Uani 1 1 d . . C16 C 0.66452(15) 0.64007(12) 0.73876(14) 0.0213(3) Uani 1 1 d . . H16 H 0.7326 0.6438 0.8117 0.026 Uiso 1 1 calc R U C17 C 0.69239(15) 0.62371(12) 0.64882(14) 0.0212(3) Uani 1 1 d . . H17 H 0.7795 0.6146 0.6601 0.025 Uiso 1 1 calc R U C18 C 0.37791(15) 0.65839(12) 0.81161(14) 0.0211(3) Uani 1 1 d . . H18A H 0.3808 0.6253 0.8797 0.025 Uiso 1 1 calc R U H18B H 0.3255 0.6192 0.7454 0.025 Uiso 1 1 calc R U C19 C 0.31326(19) 0.75380(14) 0.80236(18) 0.0382(5) Uani 1 1 d . . H19A H 0.3628 0.7922 0.8689 0.057 Uiso 1 1 calc R U H19B H 0.2259 0.7443 0.7975 0.057 Uiso 1 1 calc R U H19C H 0.3090 0.7868 0.7347 0.057 Uiso 1 1 calc R U C20 C 0.61073(16) 0.68423(12) 0.93067(13) 0.0232(4) Uani 1 1 d . . H20A H 0.5752 0.7248 0.9732 0.028 Uiso 1 1 calc R U H20B H 0.6814 0.7199 0.9226 0.028 Uiso 1 1 calc R U C21 C 0.66496(17) 0.59394(13) 0.99725(14) 0.0276(4) Uani 1 1 d . . H21A H 0.5946 0.5560 1.0009 0.041 Uiso 1 1 calc R U H21B H 0.7259 0.6106 1.0737 0.041 Uiso 1 1 calc R U H21C H 0.7094 0.5569 0.9602 0.041 Uiso 1 1 calc R U S1 S 0.04324(4) 0.54833(3) -0.33870(3) 0.02176(13) Uani 1 1 d . . O3 O 0.01939(12) 0.61950(9) -0.26901(10) 0.0307(3) Uani 1 1 d . . O4 O 0.08806(13) 0.60860(9) -0.41765(11) 0.0314(3) Uani 1 1 d D . H4 H 0.079(2) 0.5707(14) -0.4795(13) 0.047 Uiso 1 1 d D U O5 O -0.07636(12) 0.50114(10) -0.41375(10) 0.0324(3) Uani 1 1 d . . O6 O 0.14339(14) 0.48314(10) -0.27745(13) 0.0457(4) Uani 1 1 d . . 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 O1 0.0206(6) 0.0521(8) 0.0159(6) -0.0013(6) 0.0013(5) 0.0059(6) O2 0.0149(5) 0.0253(6) 0.0124(5) 0.0001(4) 0.0045(4) 0.0000(4) N1 0.0182(7) 0.0263(7) 0.0143(7) -0.0015(6) 0.0049(6) -0.0008(5) C1 0.0209(8) 0.0237(8) 0.0170(8) -0.0014(7) 0.0026(7) 0.0043(7) C2 0.0161(8) 0.0288(9) 0.0223(9) -0.0009(7) 0.0059(7) 0.0012(7) C3 0.0205(8) 0.0229(8) 0.0187(8) 0.0003(6) 0.0090(7) 0.0007(6) C4 0.0192(8) 0.0159(7) 0.0161(8) -0.0011(6) 0.0061(7) -0.0007(6) C5 0.0219(8) 0.0161(7) 0.0181(8) -0.0011(6) 0.0086(7) 0.0010(6) C6 0.0248(8) 0.0234(8) 0.0167(8) 0.0015(6) 0.0086(7) 0.0039(7) C7 0.0235(8) 0.0273(9) 0.0173(8) -0.0002(7) 0.0103(7) -0.0028(7) C8 0.0178(8) 0.0258(8) 0.0192(8) -0.0035(7) 0.0093(7) -0.0024(6) C9 0.0188(8) 0.0169(8) 0.0185(8) -0.0003(6) 0.0079(7) -0.0016(6) C10 0.0212(8) 0.0150(7) 0.0168(8) 0.0002(6) 0.0092(7) -0.0019(6) C11 0.0167(8) 0.0198(8) 0.0239(9) -0.0004(6) 0.0089(7) -0.0011(6) C12 0.0169(7) 0.0174(7) 0.0199(8) 0.0009(6) 0.0067(7) -0.0006(6) C13 0.0166(7) 0.0162(7) 0.0159(8) 0.0009(6) 0.0037(6) -0.0014(6) C14 0.0150(7) 0.0222(8) 0.0176(8) 0.0012(6) 0.0065(7) 0.0002(6) C15 0.0202(8) 0.0168(8) 0.0168(8) -0.0002(6) 0.0064(7) -0.0015(6) C16 0.0169(8) 0.0260(9) 0.0166(8) -0.0004(6) 0.0024(7) -0.0020(6) C17 0.0145(7) 0.0254(9) 0.0217(9) 0.0005(7) 0.0053(7) -0.0008(6) C18 0.0194(8) 0.0280(9) 0.0159(8) 0.0012(7) 0.0072(7) 0.0006(7) C19 0.0327(10) 0.0340(10) 0.0510(13) 0.0080(9) 0.0204(10) 0.0093(8) C20 0.0223(8) 0.0288(9) 0.0157(8) -0.0056(7) 0.0049(7) -0.0035(7) C21 0.0241(9) 0.0369(10) 0.0166(9) -0.0017(7) 0.0029(7) 0.0022(7) S1 0.0207(2) 0.0243(2) 0.0198(2) 0.00083(16) 0.00776(17) 0.00043(16) O3 0.0361(7) 0.0343(7) 0.0223(7) -0.0041(5) 0.0127(6) 0.0002(5) O4 0.0401(7) 0.0316(7) 0.0275(7) -0.0049(5) 0.0189(6) -0.0107(6) O5 0.0274(6) 0.0457(8) 0.0276(7) -0.0093(6) 0.0148(6) -0.0119(6) O6 0.0418(8) 0.0381(8) 0.0463(9) 0.0105(7) 0.0072(7) 0.0150(6) 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 C1 O1 H1 108.9(14) C10 O2 C13 121.01(12) C15 N1 C18 121.30(13) C15 N1 C20 122.88(13) C18 N1 C20 115.76(12) O1 C1 C6 121.75(15) O1 C1 C2 117.91(14) C6 C1 C2 120.34(15) C3 C2 C1 119.75(15) C3 C2 H2 120.1 C1 C2 H2 120.1 C2 C3 C4 120.40(15) C2 C3 H3 119.8 C4 C3 H3 119.8 C3 C4 C5 119.71(14) C3 C4 C10 122.94(14) C5 C4 C10 117.35(14) C6 C5 C4 119.11(14) C6 C5 C7 121.94(14) C4 C5 C7 118.92(14) C5 C6 C1 120.69(15) C5 C6 H6 119.7 C1 C6 H6 119.7 C5 C7 C8 110.97(13) C5 C7 H7A 109.4 C8 C7 H7A 109.4 C5 C7 H7B 109.4 C8 C7 H7B 109.4 H7A C7 H7B 108.0 C9 C8 C7 110.36(13) C9 C8 H8A 109.6 C7 C8 H8A 109.6 C9 C8 H8B 109.6 C7 C8 H8B 109.6 H8A C8 H8B 108.1 C11 C9 C10 118.60(14) C11 C9 C8 124.16(14) C10 C9 C8 117.20(14) O2 C10 C9 121.40(14) O2 C10 C4 115.28(13) C9 C10 C4 123.32(14) C9 C11 C12 120.90(14) C9 C11 H11 119.5 C12 C11 H11 119.5 C11 C12 C13 118.71(14) C11 C12 C17 124.74(14) C13 C12 C17 116.54(14) C14 C13 O2 116.94(13) C14 C13 C12 123.72(15) O2 C13 C12 119.33(14) C13 C14 C15 118.73(14) C13 C14 H14 120.6 C15 C14 H14 120.6 N1 C15 C14 121.77(14) N1 C15 C16 119.84(14) C14 C15 C16 118.38(14) C17 C16 C15 121.30(15) C17 C16 H16 119.4 C15 C16 H16 119.4 C16 C17 C12 121.30(15) C16 C17 H17 119.3 C12 C17 H17 119.3 N1 C18 C19 113.31(14) N1 C18 H18A 108.9 C19 C18 H18A 108.9 N1 C18 H18B 108.9 C19 C18 H18B 108.9 H18A C18 H18B 107.7 C18 C19 H19A 109.5 C18 C19 H19B 109.5 H19A C19 H19B 109.5 C18 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 N1 C20 C21 112.99(14) N1 C20 H20A 109.0 C21 C20 H20A 109.0 N1 C20 H20B 109.0 C21 C20 H20B 109.0 H20A C20 H20B 107.8 C20 C21 H21A 109.5 C20 C21 H21B 109.5 H21A C21 H21B 109.5 C20 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 O6 S1 O3 113.93(8) O6 S1 O5 113.17(9) O3 S1 O5 111.53(7) O6 S1 O4 108.19(8) O3 S1 O4 103.50(7) O5 S1 O4 105.64(7) S1 O4 H4 108.0(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.357(2) O1 H1 0.928(10) O2 C10 1.3548(18) O2 C13 1.3734(19) N1 C15 1.353(2) N1 C18 1.466(2) N1 C20 1.473(2) C1 C6 1.393(2) C1 C2 1.398(2) C2 C3 1.378(2) C2 H2 0.9500 C3 C4 1.406(2) C3 H3 0.9500 C4 C5 1.415(2) C4 C10 1.441(2) C5 C6 1.383(2) C5 C7 1.506(2) C6 H6 0.9500 C7 C8 1.524(2) C7 H7A 0.9900 C7 H7B 0.9900 C8 C9 1.506(2) C8 H8A 0.9900 C8 H8B 0.9900 C9 C11 1.386(2) C9 C10 1.387(2) C11 C12 1.393(2) C11 H11 0.9500 C12 C13 1.415(2) C12 C17 1.420(2) C13 C14 1.373(2) C14 C15 1.414(2) C14 H14 0.9500 C15 C16 1.437(2) C16 C17 1.354(2) C16 H16 0.9500 C17 H17 0.9500 C18 C19 1.510(2) C18 H18A 0.9900 C18 H18B 0.9900 C19 H19A 0.9800 C19 H19B 0.9800 C19 H19C 0.9800 C20 C21 1.518(2) C20 H20A 0.9900 C20 H20B 0.9900 C21 H21A 0.9800 C21 H21B 0.9800 C21 H21C 0.9800 S1 O6 1.4249(14) S1 O3 1.4493(13) S1 O5 1.4692(13) S1 O4 1.5706(12) O4 H4 0.936(10) 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 O1 H1 O3 0.928(10) 1.809(10) 2.7308(17) 172(2) . O4 H4 O5 0.936(10) 1.708(10) 2.6417(17) 175(2) 3_564 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 O1 C1 C2 C3 -179.43(15) C6 C1 C2 C3 0.0(2) C1 C2 C3 C4 -0.2(2) C2 C3 C4 C5 0.4(2) C2 C3 C4 C10 -179.39(15) C3 C4 C5 C6 -0.5(2) C10 C4 C5 C6 179.35(14) C3 C4 C5 C7 177.65(14) C10 C4 C5 C7 -2.5(2) C4 C5 C6 C1 0.3(2) C7 C5 C6 C1 -177.77(15) O1 C1 C6 C5 179.35(15) C2 C1 C6 C5 -0.1(2) C6 C5 C7 C8 -144.62(15) C4 C5 C7 C8 37.31(19) C5 C7 C8 C9 -53.03(17) C7 C8 C9 C11 -145.43(15) C7 C8 C9 C10 36.89(19) C13 O2 C10 C9 1.5(2) C13 O2 C10 C4 -179.33(13) C11 C9 C10 O2 -0.5(2) C8 C9 C10 O2 177.34(13) C11 C9 C10 C4 -179.55(14) C8 C9 C10 C4 -1.7(2) C3 C4 C10 O2 -16.3(2) C5 C4 C10 O2 163.93(13) C3 C4 C10 C9 162.88(15) C5 C4 C10 C9 -16.9(2) C10 C9 C11 C12 -1.4(2) C8 C9 C11 C12 -179.05(14) C9 C11 C12 C13 2.2(2) C9 C11 C12 C17 -176.93(15) C10 O2 C13 C14 178.44(13) C10 O2 C13 C12 -0.7(2) C11 C12 C13 C14 179.80(15) C17 C12 C13 C14 -1.0(2) C11 C12 C13 O2 -1.1(2) C17 C12 C13 O2 178.05(13) O2 C13 C14 C15 -177.27(13) C12 C13 C14 C15 1.8(2) C18 N1 C15 C14 11.7(2) C20 N1 C15 C14 -171.15(14) C18 N1 C15 C16 -167.28(14) C20 N1 C15 C16 9.9(2) C13 C14 C15 N1 -179.89(14) C13 C14 C15 C16 -0.9(2) N1 C15 C16 C17 178.24(15) C14 C15 C16 C17 -0.8(2) C15 C16 C17 C12 1.6(2) C11 C12 C17 C16 178.39(16) C13 C12 C17 C16 -0.7(2) C15 N1 C18 C19 -99.02(18) C20 N1 C18 C19 83.62(18) C15 N1 C20 C21 -89.30(18) C18 N1 C20 C21 88.01(17)