#------------------------------------------------------------------------------ #$Date: 2020-08-01 03:58:32 +0300 (Sat, 01 Aug 2020) $ #$Revision: 254716 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/87/1558721.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_1558721 loop_ _publ_author_name 'Berton, Cesare' 'Busiello, Daniel Maria' 'Zamuner, Stefano' 'Solari, Euro' 'Scopelliti, Rosario' 'Fadaei-Tirani, Farzaneh' 'Severin, Kay' 'Pezzato, Cristian' _publ_section_title ; Thermodynamics and kinetics of protonated merocyanine photoacids in water ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC03152F _journal_year 2020 _chemical_formula_sum 'C21 H23 N O4 S' _chemical_formula_weight 385.46 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_block_doi 10.5517/ccdc.csd.cc224csd _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-04-17 deposited with the CCDC. 2020-07-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 111.756(12) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.282(6) _cell_length_b 15.881(7) _cell_length_c 11.591(6) _cell_measurement_reflns_used 664 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 20.05 _cell_measurement_theta_min 2.33 _cell_volume 1928.8(17) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_device_type CCD _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1443 _diffrn_reflns_av_unetI/netI 0.1474 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 11443 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.975 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.599 _diffrn_reflns_theta_min 1.944 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.327 _exptl_crystal_description Block _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.180 _exptl_transmission_factor_max 0.864 _exptl_transmission_factor_min 0.864 _refine_diff_density_max 0.278 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.074 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 249 _refine_ls_number_reflns 3544 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.958 _refine_ls_R_factor_all 0.1508 _refine_ls_R_factor_gt 0.0748 _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^)+(0.0821P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1676 _refine_ls_wR_factor_ref 0.2100 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1769 _reflns_number_total 3544 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc03152f2.cif _cod_data_source_block 1_a _cod_original_cell_volume 1928.7(17) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1558721 _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 0.958 _shelx_estimated_absorpt_t_max 0.966 _shelx_res_file ; 1_a.res created by SHELXL-2014/7 TITL 1_a.res in P2(1)/c CELL 0.71073 11.2818 15.8807 11.5909 90.000 111.756 90.000 ZERR 4.000 0.0057 0.0074 0.0061 0.000 0.012 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O S UNIT 84 92 4 16 4 L.S. 20 ACTA BOND $H FMAP 2 PLAN 20 SIZE 0.22 0.2 0.18 CONF LIST 6 DFIX 0.84 0.02 O1 H1O TEMP 23.000 WGHT 0.082100 FVAR 0.57704 C1 1 0.467111 0.323841 0.229551 11.00000 0.04024 0.03972 = 0.03556 -0.00126 0.01314 -0.00137 C2 1 0.419502 0.316517 0.099542 11.00000 0.05104 0.05037 = 0.03832 -0.00830 0.01078 -0.00638 AFIX 43 H2 2 0.352759 0.279558 0.060193 11.00000 -1.20000 AFIX 0 C3 1 0.470237 0.363015 0.030932 11.00000 0.07041 0.06565 = 0.03158 -0.00572 0.01565 -0.00224 AFIX 43 H3 2 0.437281 0.357890 -0.055125 11.00000 -1.20000 AFIX 0 C4 1 0.569890 0.417705 0.087008 11.00000 0.07491 0.07347 = 0.04336 0.00281 0.02872 -0.00954 AFIX 43 H4 2 0.604859 0.448548 0.039187 11.00000 -1.20000 AFIX 0 C5 1 0.617238 0.426387 0.213884 11.00000 0.05429 0.05248 = 0.05479 -0.00654 0.02318 -0.01255 AFIX 43 H5 2 0.683641 0.463981 0.251305 11.00000 -1.20000 AFIX 0 C6 1 0.567393 0.379653 0.288148 11.00000 0.04565 0.04700 = 0.03449 -0.00618 0.01032 -0.00238 C7 1 0.610830 0.389479 0.422412 11.00000 0.05370 0.04673 = 0.03619 -0.00382 0.01081 -0.00808 AFIX 43 H7 2 0.585578 0.348966 0.466554 11.00000 -1.20000 AFIX 0 C8 1 0.684898 0.452943 0.487336 11.00000 0.05395 0.05148 = 0.03423 -0.00318 0.01280 -0.00620 AFIX 43 H8 2 0.713467 0.491845 0.443515 11.00000 -1.20000 AFIX 0 C9 1 0.722676 0.465080 0.617059 11.00000 0.03518 0.04821 = 0.03904 -0.00449 0.00953 -0.00628 C10 1 0.712684 0.403929 0.714764 11.00000 0.03818 0.04437 = 0.03610 -0.00129 0.00968 -0.00308 C11 1 0.775779 0.453832 0.832471 11.00000 0.03739 0.05219 = 0.03433 0.00246 0.01185 -0.00365 C12 1 0.809473 0.532502 0.804584 11.00000 0.03515 0.05352 = 0.02584 -0.00037 0.00940 -0.00149 C13 1 0.862119 0.594480 0.891069 11.00000 0.04936 0.04593 = 0.03892 -0.00329 0.01533 0.00112 AFIX 43 H13 2 0.883563 0.646995 0.869057 11.00000 -1.20000 AFIX 0 C14 1 0.881394 0.574373 1.012566 11.00000 0.04293 0.06787 = 0.03938 -0.00815 0.01185 0.00019 AFIX 43 H14 2 0.916283 0.614656 1.074111 11.00000 -1.20000 AFIX 0 C15 1 0.850469 0.496390 1.045339 11.00000 0.05250 0.08002 = 0.02692 0.00200 0.01332 0.00336 AFIX 43 H15 2 0.864568 0.484925 1.128069 11.00000 -1.20000 AFIX 0 C16 1 0.797823 0.434090 0.954762 11.00000 0.05362 0.05530 = 0.05078 0.00867 0.02404 -0.00542 AFIX 43 H16 2 0.778321 0.380965 0.976520 11.00000 -1.20000 AFIX 0 C17 1 0.779515 0.319495 0.714755 11.00000 0.05922 0.05349 = 0.04917 0.00315 0.01156 0.00794 AFIX 137 H17A 2 0.865705 0.329775 0.721549 11.00000 -1.50000 H17B 2 0.734530 0.289968 0.638781 11.00000 -1.50000 H17C 2 0.780017 0.286051 0.783928 11.00000 -1.50000 AFIX 0 C18 1 0.570770 0.390034 0.697423 11.00000 0.04655 0.06329 = 0.05736 -0.00237 0.01712 -0.01221 AFIX 137 H18A 2 0.566404 0.354883 0.763115 11.00000 -1.50000 H18B 2 0.526608 0.363252 0.618885 11.00000 -1.50000 H18C 2 0.531610 0.443380 0.699555 11.00000 -1.50000 AFIX 0 C19 1 0.801381 0.611249 0.609222 11.00000 0.04618 0.03783 = 0.03344 0.00211 0.01194 0.00095 AFIX 23 H19A 2 0.796869 0.661585 0.654824 11.00000 -1.20000 H19B 2 0.736023 0.615273 0.526634 11.00000 -1.20000 AFIX 0 C20 1 0.930921 0.606259 0.599410 11.00000 0.04688 0.04764 = 0.04826 0.01018 0.01391 0.00179 AFIX 23 H20A 2 0.941636 0.550558 0.570330 11.00000 -1.20000 H20B 2 0.996098 0.613625 0.681489 11.00000 -1.20000 AFIX 0 C21 1 0.950983 0.671397 0.512623 11.00000 0.04274 0.05217 = 0.03674 0.00132 0.01037 -0.00560 AFIX 23 H21A 2 1.041678 0.675525 0.529555 11.00000 -1.20000 H21B 2 0.923000 0.725702 0.531296 11.00000 -1.20000 AFIX 0 N1 3 0.776944 0.536523 0.672991 11.00000 0.04003 0.04195 = 0.02961 -0.00290 0.00994 -0.00419 O1 4 0.417814 0.279867 0.300750 11.00000 0.06388 0.05752 = 0.03851 -0.00793 0.01564 -0.02074 H1O 2 0.360574 0.246577 0.256172 11.00000 -1.20000 O2 4 0.733470 0.656654 0.328213 11.00000 0.04756 0.07918 = 0.04402 0.01337 0.01033 0.01142 O3 4 0.904559 0.565943 0.331101 11.00000 0.13286 0.04644 = 0.05378 -0.00405 0.03014 0.04097 O4 4 0.909223 0.714389 0.283710 11.00000 0.08193 0.06747 = 0.05551 0.01897 0.03942 0.00569 S1 5 0.869588 0.650346 0.350589 11.00000 0.05765 0.04045 = 0.03710 0.00609 0.01889 0.01307 HKLF 4 REM 1_a.res in P2(1)/c REM R1 = 0.0748 for 1769 Fo > 4sig(Fo) and 0.1508 for all 3544 data REM 249 parameters refined using 1 restraints END WGHT 0.0808 0.0000 REM Highest difference peak 0.278, deepest hole -0.595, 1-sigma level 0.074 Q1 1 0.8784 0.7524 0.3553 11.00000 0.05 0.28 Q2 1 1.0539 0.5274 0.6253 11.00000 0.05 0.26 Q3 1 0.4092 0.3713 0.6344 11.00000 0.05 0.25 Q4 1 0.8020 0.7130 0.2431 11.00000 0.05 0.25 Q5 1 0.9932 0.6463 0.3863 11.00000 0.05 0.25 Q6 1 0.7453 0.3571 1.0928 11.00000 0.05 0.23 Q7 1 0.9011 0.6821 0.2983 11.00000 0.05 0.22 Q8 1 0.3130 0.4101 -0.0420 11.00000 0.05 0.22 Q9 1 0.7743 0.5123 1.1373 11.00000 0.05 0.22 Q10 1 0.6738 0.4415 0.9367 11.00000 0.05 0.21 Q11 1 0.9943 0.7332 0.3358 11.00000 0.05 0.21 Q12 1 0.8844 0.3720 0.5936 11.00000 0.05 0.20 Q13 1 0.9921 0.7487 0.2147 11.00000 0.05 0.20 Q14 1 0.5626 0.2645 0.6186 11.00000 0.05 0.20 Q15 1 0.8374 0.7221 0.4387 11.00000 0.05 0.20 Q16 1 0.7688 0.6383 0.3002 11.00000 0.05 0.20 Q17 1 1.0648 0.7674 0.4148 11.00000 0.05 0.20 Q18 1 0.4247 0.1759 0.2975 11.00000 0.05 0.20 Q19 1 0.6432 0.5419 0.7860 11.00000 0.05 0.20 Q20 1 0.9731 0.3730 0.7985 11.00000 0.05 0.20 ; _shelx_res_checksum 46321 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4671(4) 0.3238(3) 0.2296(5) 0.0388(11) Uani 1 1 d . . . . . C2 C 0.4195(5) 0.3165(3) 0.0995(5) 0.0482(13) Uani 1 1 d . . . . . H2 H 0.3528 0.2796 0.0602 0.058 Uiso 1 1 calc R U . . . C3 C 0.4702(5) 0.3630(3) 0.0309(5) 0.0568(14) Uani 1 1 d . . . . . H3 H 0.4373 0.3579 -0.0551 0.068 Uiso 1 1 calc R U . . . C4 C 0.5699(5) 0.4177(3) 0.0870(5) 0.0620(15) Uani 1 1 d . . . . . H4 H 0.6049 0.4485 0.0392 0.074 Uiso 1 1 calc R U . . . C5 C 0.6172(5) 0.4264(3) 0.2139(5) 0.0530(14) Uani 1 1 d . . . . . H5 H 0.6836 0.4640 0.2513 0.064 Uiso 1 1 calc R U . . . C6 C 0.5674(4) 0.3797(3) 0.2881(5) 0.0437(12) Uani 1 1 d . . . . . C7 C 0.6108(5) 0.3895(3) 0.4224(5) 0.0472(13) Uani 1 1 d . . . . . H7 H 0.5856 0.3490 0.4666 0.057 Uiso 1 1 calc R U . . . C8 C 0.6849(4) 0.4529(3) 0.4873(5) 0.0476(13) Uani 1 1 d . . . . . H8 H 0.7135 0.4918 0.4435 0.057 Uiso 1 1 calc R U . . . C9 C 0.7227(4) 0.4651(3) 0.6171(5) 0.0420(12) Uani 1 1 d . . . . . C10 C 0.7127(4) 0.4039(3) 0.7148(5) 0.0407(12) Uani 1 1 d . . . . . C11 C 0.7758(4) 0.4538(3) 0.8325(5) 0.0417(12) Uani 1 1 d . . . . . C12 C 0.8095(4) 0.5325(3) 0.8046(4) 0.0387(11) Uani 1 1 d . . . . . C13 C 0.8621(4) 0.5945(3) 0.8911(5) 0.0450(12) Uani 1 1 d . . . . . H13 H 0.8836 0.6470 0.8691 0.054 Uiso 1 1 calc R U . . . C14 C 0.8814(4) 0.5744(3) 1.0126(5) 0.0510(13) Uani 1 1 d . . . . . H14 H 0.9163 0.6147 1.0741 0.061 Uiso 1 1 calc R U . . . C15 C 0.8505(4) 0.4964(3) 1.0453(5) 0.0535(13) Uani 1 1 d . . . . . H15 H 0.8646 0.4849 1.1281 0.064 Uiso 1 1 calc R U . . . C16 C 0.7978(5) 0.4341(3) 0.9548(5) 0.0519(14) Uani 1 1 d . . . . . H16 H 0.7783 0.3810 0.9765 0.062 Uiso 1 1 calc R U . . . C17 C 0.7795(5) 0.3195(3) 0.7148(5) 0.0564(15) Uani 1 1 d . . . . . H17A H 0.8657 0.3298 0.7215 0.085 Uiso 1 1 calc R U . . . H17B H 0.7345 0.2900 0.6388 0.085 Uiso 1 1 calc R U . . . H17C H 0.7800 0.2861 0.7839 0.085 Uiso 1 1 calc R U . . . C18 C 0.5708(4) 0.3900(3) 0.6974(6) 0.0563(14) Uani 1 1 d . . . . . H18A H 0.5664 0.3549 0.7631 0.085 Uiso 1 1 calc R U . . . H18B H 0.5266 0.3633 0.6189 0.085 Uiso 1 1 calc R U . . . H18C H 0.5316 0.4434 0.6996 0.085 Uiso 1 1 calc R U . . . C19 C 0.8014(4) 0.6112(3) 0.6092(4) 0.0400(11) Uani 1 1 d . . . . . H19A H 0.7969 0.6616 0.6548 0.048 Uiso 1 1 calc R U . . . H19B H 0.7360 0.6153 0.5266 0.048 Uiso 1 1 calc R U . . . C20 C 0.9309(5) 0.6063(3) 0.5994(5) 0.0487(13) Uani 1 1 d . . . . . H20A H 0.9416 0.5506 0.5703 0.058 Uiso 1 1 calc R U . . . H20B H 0.9961 0.6136 0.6815 0.058 Uiso 1 1 calc R U . . . C21 C 0.9510(4) 0.6714(3) 0.5126(5) 0.0451(12) Uani 1 1 d . . . . . H21A H 1.0417 0.6755 0.5296 0.054 Uiso 1 1 calc R U . . . H21B H 0.9230 0.7257 0.5313 0.054 Uiso 1 1 calc R U . . . N1 N 0.7769(3) 0.5365(2) 0.6730(4) 0.0380(9) Uani 1 1 d . . . . . O1 O 0.4178(3) 0.2799(2) 0.3007(3) 0.0543(10) Uani 1 1 d D . . . . H1O H 0.361(4) 0.247(3) 0.256(4) 0.065 Uiso 1 1 d D U . . . O2 O 0.7335(3) 0.6567(2) 0.3282(3) 0.0588(10) Uani 1 1 d . . . . . O3 O 0.9046(4) 0.5659(2) 0.3311(4) 0.0790(13) Uani 1 1 d . . . . . O4 O 0.9092(3) 0.7144(2) 0.2837(4) 0.0643(11) Uani 1 1 d . . . . . S1 S 0.86959(12) 0.65035(7) 0.35059(12) 0.0447(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 C1 0.040(3) 0.040(2) 0.036(3) -0.001(2) 0.013(2) -0.0014(19) C2 0.051(3) 0.050(3) 0.038(3) -0.008(2) 0.011(3) -0.006(2) C3 0.070(4) 0.066(3) 0.032(3) -0.006(3) 0.016(3) -0.002(3) C4 0.075(4) 0.073(4) 0.043(4) 0.003(3) 0.029(3) -0.010(3) C5 0.054(3) 0.052(3) 0.055(4) -0.007(3) 0.023(3) -0.013(2) C6 0.046(3) 0.047(3) 0.034(3) -0.006(2) 0.010(2) -0.002(2) C7 0.054(3) 0.047(3) 0.036(3) -0.004(2) 0.011(3) -0.008(2) C8 0.054(3) 0.051(3) 0.034(3) -0.003(2) 0.013(3) -0.006(2) C9 0.035(3) 0.048(3) 0.039(3) -0.004(2) 0.010(2) -0.006(2) C10 0.038(3) 0.044(3) 0.036(3) -0.001(2) 0.010(2) -0.0031(19) C11 0.037(3) 0.052(3) 0.034(3) 0.002(2) 0.012(2) -0.004(2) C12 0.035(3) 0.054(3) 0.026(3) 0.000(2) 0.009(2) -0.001(2) C13 0.049(3) 0.046(3) 0.039(3) -0.003(2) 0.015(3) 0.001(2) C14 0.043(3) 0.068(3) 0.039(3) -0.008(3) 0.012(3) 0.000(2) C15 0.053(3) 0.080(4) 0.027(3) 0.002(3) 0.013(3) 0.003(3) C16 0.054(3) 0.055(3) 0.051(4) 0.009(3) 0.024(3) -0.005(2) C17 0.059(3) 0.053(3) 0.049(4) 0.003(3) 0.012(3) 0.008(2) C18 0.047(3) 0.063(3) 0.057(4) -0.002(3) 0.017(3) -0.012(2) C19 0.046(3) 0.038(2) 0.033(3) 0.002(2) 0.012(2) 0.0009(19) C20 0.047(3) 0.048(3) 0.048(3) 0.010(2) 0.014(3) 0.002(2) C21 0.043(3) 0.052(3) 0.037(3) 0.001(2) 0.010(2) -0.006(2) N1 0.040(2) 0.042(2) 0.030(2) -0.0029(17) 0.0099(19) -0.0042(16) O1 0.064(2) 0.058(2) 0.039(2) -0.0079(17) 0.016(2) -0.0207(17) O2 0.048(2) 0.079(2) 0.044(2) 0.0134(19) 0.0103(18) 0.0114(17) O3 0.133(4) 0.046(2) 0.054(3) -0.0041(19) 0.030(3) 0.041(2) O4 0.082(3) 0.067(2) 0.056(3) 0.0190(19) 0.039(2) 0.0057(19) S1 0.0577(8) 0.0405(6) 0.0371(8) 0.0061(6) 0.0189(6) 0.0131(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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 118.3(4) . . ? O1 C1 C2 122.2(4) . . ? C6 C1 C2 119.5(4) . . ? C3 C2 C1 120.5(5) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.9(5) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 119.6(5) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 121.3(5) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.3(5) . . ? C1 C6 C7 118.5(4) . . ? C5 C6 C7 123.1(4) . . ? C8 C7 C6 124.8(5) . . ? C8 C7 H7 117.6 . . ? C6 C7 H7 117.6 . . ? C7 C8 C9 125.1(5) . . ? C7 C8 H8 117.4 . . ? C9 C8 H8 117.4 . . ? N1 C9 C8 122.3(4) . . ? N1 C9 C10 109.0(4) . . ? C8 C9 C10 128.7(4) . . ? C11 C10 C9 101.3(4) . . ? C11 C10 C17 113.0(4) . . ? C9 C10 C17 112.5(4) . . ? C11 C10 C18 108.0(4) . . ? C9 C10 C18 110.5(4) . . ? C17 C10 C18 111.0(4) . . ? C12 C11 C16 119.1(5) . . ? C12 C11 C10 110.0(4) . . ? C16 C11 C10 130.8(4) . . ? C13 C12 C11 124.1(5) . . ? C13 C12 N1 128.1(4) . . ? C11 C12 N1 107.8(4) . . ? C12 C13 C14 116.2(5) . . ? C12 C13 H13 121.9 . . ? C14 C13 H13 121.9 . . ? C15 C14 C13 121.9(5) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 C16 120.5(5) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C11 C16 C15 118.2(5) . . ? C11 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C10 C17 H17A 109.5 . . ? C10 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C10 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C10 C18 H18A 109.5 . . ? C10 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C10 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 C20 111.2(3) . . ? N1 C19 H19A 109.4 . . ? C20 C19 H19A 109.4 . . ? N1 C19 H19B 109.4 . . ? C20 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C19 C20 C21 113.6(4) . . ? C19 C20 H20A 108.8 . . ? C21 C20 H20A 108.8 . . ? C19 C20 H20B 108.8 . . ? C21 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? C20 C21 S1 115.1(3) . . ? C20 C21 H21A 108.5 . . ? S1 C21 H21A 108.5 . . ? C20 C21 H21B 108.5 . . ? S1 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C9 N1 C12 111.7(4) . . ? C9 N1 C19 125.2(4) . . ? C12 N1 C19 123.2(4) . . ? C1 O1 H1O 110(4) . . ? O3 S1 O4 114.4(2) . . ? O3 S1 O2 111.5(2) . . ? O4 S1 O2 111.7(2) . . ? O3 S1 C21 106.0(2) . . ? O4 S1 C21 106.9(2) . . ? O2 S1 C21 105.7(2) . . ? 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 C1 O1 1.348(5) . ? C1 C6 1.399(6) . ? C1 C2 1.405(7) . ? C2 C3 1.357(7) . ? C2 H2 0.9300 . ? C3 C4 1.378(7) . ? C3 H3 0.9300 . ? C4 C5 1.373(8) . ? C4 H4 0.9300 . ? C5 C6 1.402(7) . ? C5 H5 0.9300 . ? C6 C7 1.456(7) . ? C7 C8 1.347(6) . ? C7 H7 0.9300 . ? C8 C9 1.416(7) . ? C8 H8 0.9300 . ? C9 N1 1.337(5) . ? C9 C10 1.527(7) . ? C10 C11 1.509(7) . ? C10 C17 1.538(6) . ? C10 C18 1.554(6) . ? C11 C12 1.379(6) . ? C11 C16 1.381(7) . ? C12 C13 1.373(6) . ? C12 N1 1.432(6) . ? C13 C14 1.380(7) . ? C13 H13 0.9300 . ? C14 C15 1.378(7) . ? C14 H14 0.9300 . ? C15 C16 1.404(7) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N1 1.477(5) . ? C19 C20 1.509(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.517(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 S1 1.790(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? O1 H1O 0.846(19) . ? O2 S1 1.463(3) . ? O3 S1 1.439(3) . ? O4 S1 1.446(3) . ? 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 C1 C2 C3 178.8(4) . . . . ? C6 C1 C2 C3 0.1(7) . . . . ? C1 C2 C3 C4 0.6(8) . . . . ? C2 C3 C4 C5 -1.1(8) . . . . ? C3 C4 C5 C6 1.0(8) . . . . ? O1 C1 C6 C5 -179.0(4) . . . . ? C2 C1 C6 C5 -0.2(7) . . . . ? O1 C1 C6 C7 -1.9(7) . . . . ? C2 C1 C6 C7 176.9(4) . . . . ? C4 C5 C6 C1 -0.3(8) . . . . ? C4 C5 C6 C7 -177.2(5) . . . . ? C1 C6 C7 C8 -164.5(5) . . . . ? C5 C6 C7 C8 12.4(8) . . . . ? C6 C7 C8 C9 176.9(5) . . . . ? C7 C8 C9 N1 -167.9(5) . . . . ? C7 C8 C9 C10 13.0(8) . . . . ? N1 C9 C10 C11 -2.2(5) . . . . ? C8 C9 C10 C11 177.0(5) . . . . ? N1 C9 C10 C17 -123.2(4) . . . . ? C8 C9 C10 C17 56.0(6) . . . . ? N1 C9 C10 C18 112.1(4) . . . . ? C8 C9 C10 C18 -68.7(6) . . . . ? C9 C10 C11 C12 2.9(5) . . . . ? C17 C10 C11 C12 123.6(4) . . . . ? C18 C10 C11 C12 -113.3(4) . . . . ? C9 C10 C11 C16 -180.0(5) . . . . ? C17 C10 C11 C16 -59.3(7) . . . . ? C18 C10 C11 C16 63.8(6) . . . . ? C16 C11 C12 C13 -1.4(7) . . . . ? C10 C11 C12 C13 176.1(4) . . . . ? C16 C11 C12 N1 179.9(4) . . . . ? C10 C11 C12 N1 -2.6(5) . . . . ? C11 C12 C13 C14 0.2(7) . . . . ? N1 C12 C13 C14 178.6(4) . . . . ? C12 C13 C14 C15 0.5(7) . . . . ? C13 C14 C15 C16 0.1(7) . . . . ? C12 C11 C16 C15 1.9(7) . . . . ? C10 C11 C16 C15 -175.0(5) . . . . ? C14 C15 C16 C11 -1.3(7) . . . . ? N1 C19 C20 C21 168.2(4) . . . . ? C19 C20 C21 S1 -75.0(5) . . . . ? C8 C9 N1 C12 -178.4(4) . . . . ? C10 C9 N1 C12 0.8(5) . . . . ? C8 C9 N1 C19 1.6(7) . . . . ? C10 C9 N1 C19 -179.2(4) . . . . ? C13 C12 N1 C9 -177.5(4) . . . . ? C11 C12 N1 C9 1.1(5) . . . . ? C13 C12 N1 C19 2.4(7) . . . . ? C11 C12 N1 C19 -178.9(4) . . . . ? C20 C19 N1 C9 -89.5(5) . . . . ? C20 C19 N1 C12 90.5(5) . . . . ? C20 C21 S1 O3 -52.5(4) . . . . ? C20 C21 S1 O4 -174.9(3) . . . . ? C20 C21 S1 O2 66.0(4) . . . . ?