#------------------------------------------------------------------------------ #$Date: 2020-05-07 23:56:45 +0300 (Thu, 07 May 2020) $ #$Revision: 251887 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240488.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_7240488 loop_ _publ_author_name 'Meng, Fan-Fei' 'Wu, Lei' 'Gu, Yu-Cheng' 'Zhou, Sha' 'Li, Yong-Hong' 'Chen, Ming-Gui' 'Zhou, Shaa' 'Zhao, Yang-Yang' 'Ma, Yi' 'Li, Zheng-Ming' _publ_section_title ; Research on the controllable degradation of N-methylamido and dialkylamino substituted at the 5th position of the benzene ring in chlorsulfuron in acidic soil ; _journal_issue 30 _journal_name_full 'RSC Advances' _journal_page_first 17870 _journal_paper_doi 10.1039/D0RA00811G _journal_volume 10 _journal_year 2020 _chemical_formula_sum 'C16 H19 Cl N6 O4 S' _chemical_formula_weight 426.88 _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_creation_method SHELXL-2018/3 _audit_update_record ; 2020-01-07 deposited with the CCDC. 2020-04-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.533(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.2847(5) _cell_length_b 17.1412(7) _cell_length_c 11.2410(5) _cell_measurement_reflns_used 12430 _cell_measurement_temperature 113(2) _cell_measurement_theta_max 32.4900 _cell_measurement_theta_min 2.0200 _cell_volume 1934.48(15) _computing_cell_refinement crystalclear _computing_data_collection crystalclear _computing_data_reduction crystalclear _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 113(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_unetI/netI 0.0279 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 20402 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.372 _diffrn_reflns_theta_min 2.028 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.342 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.51980 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details crystalclear _exptl_crystal_density_diffrn 1.466 _exptl_crystal_F_000 888 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.621 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.058 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 3952 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0496 _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^)+(0.0639P)^2^+1.6125P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1274 _refine_ls_wR_factor_ref 0.1345 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3383 _reflns_number_total 3952 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra00811g2.cif _cod_data_source_block r20191117b _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 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240488 _shelx_shelxl_version_number 2018/3 _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 0.935 _shelx_estimated_absorpt_t_max 0.960 _shelx_res_file ; TITL r20191117b in P2(1)/c r20191117b.res created by SHELXL-2018/3 at 09:59:17 on 18-Nov-2019 CELL 0.71073 10.284751 17.141157 11.240965 90.0000 102.5331 90.0000 ZERR 4.00 0.000473 0.000707 0.000525 0.0000 0.0045 0.0000 LATT 1 SYMM -x, y+1/2,-z+1/2 SFAC C H N O Cl S UNIT 64 76 24 16 4 4 L.S. 4 ACTA CONF HTAB SIZE 0.20 0.18 0.12 TEMP -160 BOND $H FMAP 2 PLAN 20 DFIX 0.90 0.01 N2 H2 N3 H3 WGHT 0.063900 1.612500 FVAR 6.87437 MOLE 1 S1 6 0.325377 0.136763 0.780942 11.00000 0.03829 0.03520 = 0.03845 -0.00564 0.01198 -0.00299 CL1 5 0.146019 0.231344 0.545906 11.00000 0.06063 0.03651 = 0.05049 0.00795 0.02476 0.00870 O1 4 0.381273 0.076907 0.864241 11.00000 0.04230 0.04893 = 0.04631 0.00476 -0.00040 -0.00531 O2 4 0.315915 0.214579 0.823841 11.00000 0.05986 0.04208 = 0.04896 -0.01525 0.02344 -0.00459 O3 4 0.405072 0.021588 0.608897 11.00000 0.03771 0.02941 = 0.06282 -0.01217 0.01965 -0.00678 O4 4 0.783277 0.246398 0.329512 11.00000 0.05016 0.04536 = 0.04821 0.00668 0.01975 0.00215 N1 3 -0.048108 -0.063348 0.726192 11.00000 0.03627 0.04489 = 0.05589 0.00431 0.01471 -0.00587 N2 3 0.416617 0.147258 0.678350 11.00000 0.03785 0.02770 = 0.04997 -0.00942 0.01887 -0.00462 H2 2 0.441850 0.194574 0.658813 11.00000 -1.20000 N3 3 0.527930 0.108816 0.529064 11.00000 0.03419 0.02715 = 0.05043 -0.01343 0.01456 -0.00373 H3 2 0.548278 0.069599 0.484140 11.00000 -1.20000 N4 3 0.654544 0.179360 0.425837 11.00000 0.03237 0.03379 = 0.04031 -0.00408 0.00912 -0.00051 N5 3 0.553662 0.242790 0.570388 11.00000 0.02978 0.02899 = 0.03818 -0.00665 0.00603 -0.00117 N6 3 0.686978 0.315734 0.464074 11.00000 0.03831 0.03150 = 0.03887 0.00371 0.00266 0.00132 C1 1 -0.259439 -0.012242 0.840040 11.00000 0.08900 0.07108 = 0.08818 -0.02729 0.05654 -0.02068 AFIX 93 H1A 2 -0.171345 0.005808 0.871470 11.00000 -1.20000 H1B 2 -0.330275 0.004776 0.875637 11.00000 -1.20000 AFIX 0 C2 1 -0.283145 -0.060416 0.747964 11.00000 0.04388 0.06306 = 0.05940 -0.01099 0.02157 -0.01052 AFIX 43 H2A 2 -0.372745 -0.076858 0.719697 11.00000 -1.20000 AFIX 0 C3 1 -0.182255 -0.092155 0.682784 11.00000 0.04352 0.04806 = 0.05039 -0.01111 0.01813 -0.01094 AFIX 23 H3A 2 -0.181022 -0.149707 0.690335 11.00000 -1.20000 H3B 2 -0.211047 -0.079391 0.595115 11.00000 -1.20000 AFIX 0 C4 1 0.036318 -0.105364 0.826328 11.00000 0.05343 0.05252 = 0.09979 0.03213 0.00938 -0.00652 AFIX 137 H4A 2 0.124231 -0.113706 0.808095 11.00000 -1.50000 H4B 2 -0.004280 -0.155894 0.836948 11.00000 -1.50000 H4C 2 0.045886 -0.074803 0.901411 11.00000 -1.50000 AFIX 0 C5 1 -0.005577 0.005979 0.686282 11.00000 0.03365 0.04024 = 0.03787 -0.00372 0.01531 0.00234 C6 1 -0.081516 0.048879 0.589145 11.00000 0.03067 0.04732 = 0.04000 -0.00577 0.01286 0.00509 AFIX 43 H6 2 -0.168102 0.031130 0.551231 11.00000 -1.20000 AFIX 0 C7 1 -0.032956 0.116150 0.547780 11.00000 0.03727 0.04739 = 0.03407 0.00130 0.01288 0.01477 AFIX 43 H7 2 -0.086016 0.142995 0.480492 11.00000 -1.20000 AFIX 0 C8 1 0.091224 0.145726 0.601680 11.00000 0.04155 0.03380 = 0.03649 -0.00032 0.01866 0.00840 C9 1 0.168142 0.104477 0.699473 11.00000 0.03231 0.03648 = 0.03323 -0.00352 0.01387 0.00324 C10 1 0.121162 0.035753 0.740091 11.00000 0.03445 0.03715 = 0.03531 0.00173 0.00944 0.00266 AFIX 43 H10 2 0.175724 0.008165 0.805677 11.00000 -1.20000 AFIX 0 C11 1 0.446653 0.088131 0.606974 11.00000 0.02464 0.03244 = 0.04706 -0.00958 0.00990 -0.00161 C12 1 0.579958 0.180360 0.508617 11.00000 0.02519 0.03355 = 0.03538 -0.00562 0.00414 -0.00042 C13 1 0.705731 0.248715 0.408992 11.00000 0.03223 0.04071 = 0.03395 0.00381 0.00673 0.00355 C14 1 0.608835 0.309436 0.543642 11.00000 0.03087 0.03360 = 0.03365 0.00013 0.00095 0.00199 C15 1 0.580309 0.380774 0.609426 11.00000 0.04864 0.02606 = 0.04708 -0.00408 -0.00069 0.00137 AFIX 137 H15A 2 0.627341 0.377619 0.695007 11.00000 -1.50000 H15B 2 0.484263 0.384628 0.604760 11.00000 -1.50000 H15C 2 0.610570 0.426970 0.571758 11.00000 -1.50000 AFIX 0 C16 1 0.844500 0.318043 0.303896 11.00000 0.06830 0.05203 = 0.06632 0.01267 0.03852 -0.00274 AFIX 137 H16A 2 0.775223 0.356244 0.270675 11.00000 -1.50000 H16B 2 0.899450 0.308259 0.244313 11.00000 -1.50000 H16C 2 0.900565 0.338472 0.379236 11.00000 -1.50000 AFIX 0 HKLF 4 REM r20191117b in P2(1)/c REM wR2 = 0.1345, GooF = S = 1.040, Restrained GooF = 1.039 for all data REM R1 = 0.0496 for 3383 Fo > 4sig(Fo) and 0.0589 for all 3952 data REM 262 parameters refined using 2 restraints END WGHT 0.0627 1.6064 REM Instructions for potential hydrogen bonds HTAB N2 N5 EQIV $1 -x+1, -y, -z+1 HTAB N3 O3_$1 EQIV $2 -x, y-1/2, -z+3/2 HTAB C4 Cl1_$2 EQIV $3 x-1, y, z HTAB C7 O4_$3 HTAB C7 N4_$3 REM Highest difference peak 0.621, deepest hole -0.548, 1-sigma level 0.058 Q1 1 0.3791 0.1503 0.7373 11.00000 0.05 0.62 Q2 1 0.6419 0.3836 0.5560 11.00000 0.05 0.46 Q3 1 0.0025 -0.0831 0.8975 11.00000 0.05 0.34 Q4 1 0.5147 0.3833 0.6628 11.00000 0.05 0.33 Q5 1 -0.0337 -0.0590 0.9525 11.00000 0.05 0.29 Q6 1 0.4286 0.0963 0.8147 11.00000 0.05 0.29 Q7 1 0.2518 0.1221 0.7349 11.00000 0.05 0.28 Q8 1 0.7472 0.3394 0.4368 11.00000 0.05 0.27 Q9 1 0.2013 0.2703 0.5482 11.00000 0.05 0.25 Q10 1 0.2846 0.2504 0.7728 11.00000 0.05 0.25 Q11 1 0.0000 0.0000 1.0000 10.50000 0.05 0.22 Q12 1 0.0405 0.1282 0.5617 11.00000 0.05 0.21 Q13 1 0.6620 0.2986 0.4163 11.00000 0.05 0.20 Q14 1 0.6602 0.3159 0.5135 11.00000 0.05 0.20 Q15 1 0.6951 0.1960 0.3957 11.00000 0.05 0.20 Q16 1 0.8436 0.2630 0.2767 11.00000 0.05 0.20 Q17 1 0.2853 0.1810 0.7734 11.00000 0.05 0.19 Q18 1 0.1603 0.0640 0.7037 11.00000 0.05 0.19 Q19 1 0.1227 -0.1371 0.7773 11.00000 0.05 0.19 Q20 1 0.1285 0.1321 0.6464 11.00000 0.05 0.19 ; _shelx_res_checksum 64136 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 S1 S 0.32538(6) 0.13676(4) 0.78094(6) 0.03676(18) Uani 1 1 d . . . . . Cl1 Cl 0.14602(7) 0.23134(4) 0.54591(6) 0.0473(2) Uani 1 1 d . . . . . O1 O 0.38127(18) 0.07691(11) 0.86424(17) 0.0474(5) Uani 1 1 d . . . . . O2 O 0.3159(2) 0.21458(11) 0.82384(18) 0.0485(5) Uani 1 1 d . . . . . O3 O 0.40507(17) 0.02159(10) 0.60890(18) 0.0420(4) Uani 1 1 d . . . . . O4 O 0.78328(19) 0.24640(11) 0.32951(17) 0.0465(5) Uani 1 1 d . . . . . N1 N -0.0481(2) -0.06335(13) 0.7262(2) 0.0450(5) Uani 1 1 d . . . . . N2 N 0.4166(2) 0.14726(12) 0.6784(2) 0.0371(5) Uani 1 1 d D . . . . H2 H 0.442(3) 0.1946(9) 0.659(3) 0.045 Uiso 1 1 d D U . . . N3 N 0.5279(2) 0.10882(11) 0.5291(2) 0.0364(5) Uani 1 1 d D . . . . H3 H 0.548(3) 0.0696(12) 0.484(2) 0.044 Uiso 1 1 d D U . . . N4 N 0.6545(2) 0.17936(12) 0.42584(19) 0.0353(5) Uani 1 1 d . . . . . N5 N 0.55366(19) 0.24279(11) 0.57039(18) 0.0325(4) Uani 1 1 d . . . . . N6 N 0.6870(2) 0.31573(12) 0.46407(19) 0.0371(5) Uani 1 1 d . . . . . C1 C -0.2594(4) -0.0122(2) 0.8400(4) 0.0771(11) Uani 1 1 d . . . . . H1A H -0.171345 0.005808 0.871470 0.093 Uiso 1 1 calc R U . . . H1B H -0.330275 0.004776 0.875637 0.093 Uiso 1 1 calc R U . . . C2 C -0.2831(3) -0.06042(19) 0.7480(3) 0.0539(7) Uani 1 1 d . . . . . H2A H -0.372745 -0.076858 0.719697 0.065 Uiso 1 1 calc R U . . . C3 C -0.1823(3) -0.09216(17) 0.6828(3) 0.0461(6) Uani 1 1 d . . . . . H3A H -0.181022 -0.149707 0.690335 0.055 Uiso 1 1 calc R U . . . H3B H -0.211047 -0.079391 0.595115 0.055 Uiso 1 1 calc R U . . . C4 C 0.0363(3) -0.1054(2) 0.8263(4) 0.0697(10) Uani 1 1 d . . . . . H4A H 0.124231 -0.113706 0.808095 0.105 Uiso 1 1 calc R U . . . H4B H -0.004280 -0.155894 0.836948 0.105 Uiso 1 1 calc R U . . . H4C H 0.045886 -0.074803 0.901411 0.105 Uiso 1 1 calc R U . . . C5 C -0.0056(2) 0.00598(15) 0.6863(2) 0.0361(5) Uani 1 1 d . . . . . C6 C -0.0815(2) 0.04888(15) 0.5891(2) 0.0385(6) Uani 1 1 d . . . . . H6 H -0.168102 0.031130 0.551231 0.046 Uiso 1 1 calc R U . . . C7 C -0.0330(3) 0.11615(16) 0.5478(2) 0.0388(6) Uani 1 1 d . . . . . H7 H -0.086016 0.142995 0.480492 0.047 Uiso 1 1 calc R U . . . C8 C 0.0912(3) 0.14573(14) 0.6017(2) 0.0357(5) Uani 1 1 d . . . . . C9 C 0.1681(2) 0.10448(14) 0.6995(2) 0.0330(5) Uani 1 1 d . . . . . C10 C 0.1212(2) 0.03575(14) 0.7401(2) 0.0354(5) Uani 1 1 d . . . . . H10 H 0.175724 0.008165 0.805677 0.042 Uiso 1 1 calc R U . . . C11 C 0.4467(2) 0.08813(14) 0.6070(2) 0.0344(5) Uani 1 1 d . . . . . C12 C 0.5800(2) 0.18036(13) 0.5086(2) 0.0317(5) Uani 1 1 d . . . . . C13 C 0.7057(2) 0.24872(15) 0.4090(2) 0.0357(5) Uani 1 1 d . . . . . C14 C 0.6088(2) 0.30944(14) 0.5436(2) 0.0336(5) Uani 1 1 d . . . . . C15 C 0.5803(3) 0.38077(14) 0.6094(2) 0.0423(6) Uani 1 1 d . . . . . H15A H 0.627341 0.377619 0.695007 0.063 Uiso 1 1 calc R U . . . H15B H 0.484263 0.384628 0.604760 0.063 Uiso 1 1 calc R U . . . H15C H 0.610570 0.426970 0.571758 0.063 Uiso 1 1 calc R U . . . C16 C 0.8445(3) 0.31804(18) 0.3039(3) 0.0586(8) Uani 1 1 d . . . . . H16A H 0.775223 0.356244 0.270675 0.088 Uiso 1 1 calc R U . . . H16B H 0.899450 0.308259 0.244313 0.088 Uiso 1 1 calc R U . . . H16C H 0.900565 0.338472 0.379236 0.088 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 0.0383(3) 0.0352(3) 0.0385(3) -0.0056(2) 0.0120(3) -0.0030(2) Cl1 0.0606(4) 0.0365(3) 0.0505(4) 0.0080(3) 0.0248(3) 0.0087(3) O1 0.0423(10) 0.0489(11) 0.0463(10) 0.0048(8) -0.0004(8) -0.0053(8) O2 0.0599(12) 0.0421(10) 0.0490(11) -0.0153(8) 0.0234(9) -0.0046(9) O3 0.0377(9) 0.0294(9) 0.0628(12) -0.0122(8) 0.0197(8) -0.0068(7) O4 0.0502(11) 0.0454(11) 0.0482(11) 0.0067(8) 0.0198(9) 0.0021(8) N1 0.0363(11) 0.0449(13) 0.0559(14) 0.0043(10) 0.0147(10) -0.0059(9) N2 0.0379(11) 0.0277(10) 0.0500(12) -0.0094(9) 0.0189(9) -0.0046(8) N3 0.0342(11) 0.0272(10) 0.0504(12) -0.0134(9) 0.0146(9) -0.0037(8) N4 0.0324(10) 0.0338(11) 0.0403(11) -0.0041(8) 0.0091(8) -0.0005(8) N5 0.0298(10) 0.0290(10) 0.0382(11) -0.0066(8) 0.0060(8) -0.0012(8) N6 0.0383(11) 0.0315(11) 0.0389(11) 0.0037(8) 0.0027(9) 0.0013(8) C1 0.089(3) 0.071(2) 0.088(3) -0.027(2) 0.057(2) -0.021(2) C2 0.0439(16) 0.0631(19) 0.0594(18) -0.0110(15) 0.0216(14) -0.0105(14) C3 0.0435(15) 0.0481(16) 0.0504(15) -0.0111(12) 0.0181(12) -0.0109(12) C4 0.0534(18) 0.0525(19) 0.100(3) 0.0321(18) 0.0094(18) -0.0065(15) C5 0.0336(12) 0.0402(13) 0.0379(13) -0.0037(10) 0.0153(10) 0.0023(10) C6 0.0307(12) 0.0473(15) 0.0400(13) -0.0058(11) 0.0129(10) 0.0051(10) C7 0.0373(13) 0.0474(15) 0.0341(12) 0.0013(10) 0.0129(10) 0.0148(11) C8 0.0416(13) 0.0338(12) 0.0365(12) -0.0003(10) 0.0187(10) 0.0084(10) C9 0.0323(12) 0.0365(13) 0.0332(12) -0.0035(9) 0.0139(9) 0.0032(10) C10 0.0344(12) 0.0372(13) 0.0353(12) 0.0017(10) 0.0094(10) 0.0027(10) C11 0.0246(11) 0.0324(12) 0.0471(14) -0.0096(10) 0.0099(10) -0.0016(9) C12 0.0252(11) 0.0335(12) 0.0354(12) -0.0056(9) 0.0041(9) -0.0004(9) C13 0.0322(12) 0.0407(14) 0.0340(12) 0.0038(10) 0.0067(10) 0.0036(10) C14 0.0309(12) 0.0336(12) 0.0336(12) 0.0001(9) 0.0010(9) 0.0020(9) C15 0.0486(15) 0.0261(12) 0.0471(15) -0.0041(10) -0.0007(12) 0.0014(11) C16 0.068(2) 0.0520(18) 0.066(2) 0.0127(15) 0.0385(17) -0.0027(15) 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' Cl Cl 0.1484 0.1585 '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 119.88(12) . . ? O1 S1 N2 109.22(12) . . ? O2 S1 N2 103.02(11) . . ? O1 S1 C9 108.00(11) . . ? O2 S1 C9 110.24(12) . . ? N2 S1 C9 105.54(11) . . ? C13 O4 C16 117.7(2) . . ? C5 N1 C3 122.2(2) . . ? C5 N1 C4 120.1(2) . . ? C3 N1 C4 117.2(2) . . ? C11 N2 S1 124.39(17) . . ? C11 N2 H2 114.4(19) . . ? S1 N2 H2 120.8(19) . . ? C12 N3 C11 130.1(2) . . ? C12 N3 H3 115.4(19) . . ? C11 N3 H3 114.4(19) . . ? C12 N4 C13 113.2(2) . . ? C12 N5 C14 115.1(2) . . ? C14 N6 C13 114.2(2) . . ? C2 C1 H1A 120.0 . . ? C2 C1 H1B 120.0 . . ? H1A C1 H1B 120.0 . . ? C1 C2 C3 126.0(3) . . ? C1 C2 H2A 117.0 . . ? C3 C2 H2A 117.0 . . ? N1 C3 C2 115.0(2) . . ? N1 C3 H3A 108.5 . . ? C2 C3 H3A 108.5 . . ? N1 C3 H3B 108.5 . . ? C2 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 C6 122.9(2) . . ? N1 C5 C10 120.2(2) . . ? C6 C5 C10 116.8(2) . . ? C7 C6 C5 121.3(2) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C6 C7 C8 121.8(2) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C7 C8 C9 118.0(2) . . ? C7 C8 Cl1 119.46(19) . . ? C9 C8 Cl1 122.6(2) . . ? C10 C9 C8 120.6(2) . . ? C10 C9 S1 116.14(18) . . ? C8 C9 S1 123.18(19) . . ? C9 C10 C5 121.5(2) . . ? C9 C10 H10 119.3 . . ? C5 C10 H10 119.3 . . ? O3 C11 N2 123.9(2) . . ? O3 C11 N3 120.9(2) . . ? N2 C11 N3 115.2(2) . . ? N4 C12 N5 126.0(2) . . ? N4 C12 N3 114.2(2) . . ? N5 C12 N3 119.8(2) . . ? O4 C13 N4 112.6(2) . . ? O4 C13 N6 120.5(2) . . ? N4 C13 N6 126.9(2) . . ? N6 C14 N5 124.6(2) . . ? N6 C14 C15 118.7(2) . . ? N5 C14 C15 116.7(2) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 1.4235(19) . ? S1 O2 1.4288(19) . ? S1 N2 1.647(2) . ? S1 C9 1.766(2) . ? Cl1 C8 1.737(3) . ? O3 C11 1.220(3) . ? O4 C13 1.321(3) . ? O4 C16 1.437(3) . ? N1 C5 1.375(3) . ? N1 C3 1.447(3) . ? N1 C4 1.454(4) . ? N2 C11 1.369(3) . ? N2 H2 0.893(10) . ? N3 C12 1.377(3) . ? N3 C11 1.382(3) . ? N3 H3 0.893(10) . ? N4 C12 1.328(3) . ? N4 C13 1.330(3) . ? N5 C12 1.335(3) . ? N5 C14 1.338(3) . ? N6 C14 1.330(3) . ? N6 C13 1.339(3) . ? C1 C2 1.305(5) . ? C1 H1A 0.9500 . ? C1 H1B 0.9500 . ? C2 C3 1.496(4) . ? C2 H2A 0.9500 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.405(4) . ? C5 C10 1.408(3) . ? C6 C7 1.377(4) . ? C6 H6 0.9500 . ? C7 C8 1.385(4) . ? C7 H7 0.9500 . ? C8 C9 1.399(3) . ? C9 C10 1.388(3) . ? C10 H10 0.9500 . ? C14 C15 1.491(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N2 C11 55.2(2) . . . . ? O2 S1 N2 C11 -176.3(2) . . . . ? C9 S1 N2 C11 -60.7(2) . . . . ? C5 N1 C3 C2 -84.3(3) . . . . ? C4 N1 C3 C2 87.8(4) . . . . ? C1 C2 C3 N1 -2.1(5) . . . . ? C3 N1 C5 C6 -9.0(4) . . . . ? C4 N1 C5 C6 179.2(3) . . . . ? C3 N1 C5 C10 173.4(2) . . . . ? C4 N1 C5 C10 1.5(4) . . . . ? N1 C5 C6 C7 -176.8(2) . . . . ? C10 C5 C6 C7 0.9(3) . . . . ? C5 C6 C7 C8 -1.6(4) . . . . ? C6 C7 C8 C9 0.9(3) . . . . ? C6 C7 C8 Cl1 -179.44(18) . . . . ? C7 C8 C9 C10 0.5(3) . . . . ? Cl1 C8 C9 C10 -179.16(18) . . . . ? C7 C8 C9 S1 -177.52(18) . . . . ? Cl1 C8 C9 S1 2.8(3) . . . . ? O1 S1 C9 C10 8.4(2) . . . . ? O2 S1 C9 C10 -124.33(19) . . . . ? N2 S1 C9 C10 125.08(18) . . . . ? O1 S1 C9 C8 -173.55(19) . . . . ? O2 S1 C9 C8 53.8(2) . . . . ? N2 S1 C9 C8 -56.8(2) . . . . ? C8 C9 C10 C5 -1.2(4) . . . . ? S1 C9 C10 C5 176.98(18) . . . . ? N1 C5 C10 C9 178.2(2) . . . . ? C6 C5 C10 C9 0.4(3) . . . . ? S1 N2 C11 O3 2.6(4) . . . . ? S1 N2 C11 N3 -178.19(18) . . . . ? C12 N3 C11 O3 176.7(2) . . . . ? C12 N3 C11 N2 -2.6(4) . . . . ? C13 N4 C12 N5 0.9(3) . . . . ? C13 N4 C12 N3 -178.9(2) . . . . ? C14 N5 C12 N4 0.3(3) . . . . ? C14 N5 C12 N3 -179.9(2) . . . . ? C11 N3 C12 N4 -179.6(2) . . . . ? C11 N3 C12 N5 0.5(4) . . . . ? C16 O4 C13 N4 -179.9(2) . . . . ? C16 O4 C13 N6 -0.7(4) . . . . ? C12 N4 C13 O4 177.9(2) . . . . ? C12 N4 C13 N6 -1.3(3) . . . . ? C14 N6 C13 O4 -178.7(2) . . . . ? C14 N6 C13 N4 0.4(4) . . . . ? C13 N6 C14 N5 1.1(3) . . . . ? C13 N6 C14 C15 -179.5(2) . . . . ? C12 N5 C14 N6 -1.4(3) . . . . ? C12 N5 C14 C15 179.2(2) . . . . ?