#------------------------------------------------------------------------------ #$Date: 2020-05-07 23:56:45 +0300 (Thu, 07 May 2020) $ #$Revision: 251887 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240487.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_7240487 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_moiety 'C17 H19 Cl N6 O5 S' _chemical_formula_sum 'C17 H16 Cl N6 O5 S' _chemical_formula_weight 451.87 _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 mixed _atom_sites_solution_primary direct _audit_creation_date 2019-12-27 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-01-07 deposited with the CCDC. 2020-04-07 downloaded from the CCDC. ; _cell_angle_alpha 85.32(3) _cell_angle_beta 81.63(3) _cell_angle_gamma 72.73(3) _cell_formula_units_Z 2 _cell_length_a 7.8939(16) _cell_length_b 8.9985(18) _cell_length_c 14.466(3) _cell_measurement_reflns_used 3013 _cell_measurement_temperature 113(2) _cell_measurement_theta_max 27.8386 _cell_measurement_theta_min 1.4240 _cell_volume 970.0(4) _computing_cell_refinement crystalclear _computing_data_collection crystalclear _computing_data_reduction crystalclear _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 113.15 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku Saturn 70 CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator confocal _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_unetI/netI 0.0346 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 9370 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.026 _diffrn_reflns_theta_max 25.026 _diffrn_reflns_theta_min 2.372 _exptl_absorpt_coefficient_mu 0.350 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.8885 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details crystalclear _exptl_crystal_density_diffrn 1.547 _exptl_crystal_description block _exptl_crystal_F_000 466 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _refine_diff_density_max 1.674 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.081 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 274 _refine_ls_number_reflns 3424 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0570 _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^)+(0.0863P)^2^+1.5493P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1506 _refine_ls_wR_factor_ref 0.1597 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2857 _reflns_number_total 3424 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra00811g2.cif _cod_data_source_block shelxl _cod_database_code 7240487 _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_max 0.959 _shelx_estimated_absorpt_t_min 0.933 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Rigid bond restraints N5, N6, C15 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002 3.a Riding coordinates: N2(H2) 3.b Ternary CH refined with riding coordinates: C3(H3A) 3.c Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C2(H2A,H2B) 3.d Aromatic/amide H refined with riding coordinates: N3(H3), C7(H7), C8(H8), C11(H11) 3.e Idealised Me refined as rotating group: C5(H5A,H5B,H5C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C) ; _shelx_res_file ; TITL shelxl in P-1 shelxl.res created by SHELXL-2018/3 at 09:35:40 on 27-Dec-2019 CELL 0.71073 7.8939 8.9985 14.4665 85.316 81.634 72.729 ZERR 2 0.0016 0.0018 0.0029 0.03 0.03 0.03 LATT 1 SFAC C H Cl N O S UNIT 34 32 2 12 10 2 EQIV $1 1+X,-1+Y,+Z DELU 0.001 0.002 N5 N6 C15 L.S. 12 PLAN 20 SIZE 0.2 0.18 0.12 TEMP -160 HTAB C3 O4 HTAB C5 Cl1_$1 BOND $H HTAB CONF fmap 2 acta SHEL 99 0.84 OMIT 0 0 1 REM REM REM WGHT 0.086300 1.549300 FVAR 0.65026 S1 6 -0.191444 0.197518 0.395164 11.00000 0.02771 0.01587 = 0.01839 -0.00019 -0.00477 -0.00227 CL1 3 -0.541571 0.072422 0.382749 11.00000 0.02098 0.02720 = 0.03020 -0.00057 -0.00238 0.00172 O1 5 0.465784 -0.447829 0.261735 11.00000 0.02094 0.01994 = 0.02618 0.00398 -0.00016 0.00051 O2 5 -0.332656 0.263234 0.467130 11.00000 0.04069 0.02235 = 0.01973 -0.00391 0.00076 -0.00061 O3 5 -0.014443 0.205083 0.400204 11.00000 0.03114 0.02224 = 0.03643 -0.00212 -0.01244 -0.00673 O4 5 -0.023267 0.151081 0.198156 11.00000 0.02591 0.02689 = 0.03051 -0.00072 0.00287 0.00143 O5 5 0.135280 0.204467 -0.132339 11.00000 0.04071 0.04090 = 0.03714 -0.00078 -0.00221 -0.00755 N1 4 0.191291 -0.369210 0.344899 11.00000 0.02152 0.01453 = 0.01866 0.00326 -0.00384 -0.00253 N2 4 -0.260702 0.289279 0.298007 11.00000 0.02316 0.02159 = 0.01934 0.00432 -0.00100 -0.00275 AFIX 3 H2 2 -0.370232 0.286729 0.294737 11.00000 -1.20000 AFIX 0 N3 4 -0.232381 0.366596 0.143281 11.00000 0.02732 0.02540 = 0.01895 0.00147 -0.00052 -0.00502 AFIX 43 H3 2 -0.333017 0.436364 0.163097 11.00000 -1.20000 AFIX 0 N4 4 -0.262119 0.512697 0.006711 11.00000 0.04841 0.03606 = 0.02387 0.01066 -0.01205 -0.02404 N5 4 -0.073261 0.436136 -0.130390 11.00000 0.03966 0.03903 = 0.04116 0.00175 -0.01214 -0.02127 N6 4 -0.037171 0.268218 0.009118 11.00000 0.03080 0.04456 = 0.02914 -0.00922 0.00056 -0.01920 C1 1 0.373159 -0.214515 0.112367 11.00000 0.02768 0.03032 = 0.02573 0.00810 -0.00147 -0.00800 AFIX 23 H1A 2 0.469091 -0.310877 0.094788 11.00000 -1.20000 H1B 2 0.308915 -0.157807 0.060280 11.00000 -1.20000 AFIX 0 C2 1 0.401331 -0.121191 0.185142 11.00000 0.03861 0.02823 = 0.03978 0.01080 -0.01152 -0.01764 AFIX 23 H2A 2 0.354495 -0.006420 0.178407 11.00000 -1.20000 H2B 2 0.514701 -0.159519 0.212922 11.00000 -1.20000 AFIX 0 C3 1 0.267159 -0.213002 0.208017 11.00000 0.02163 0.02048 = 0.02198 0.00327 -0.00372 -0.00293 AFIX 13 H3A 2 0.138022 -0.151621 0.213253 11.00000 -1.20000 AFIX 0 C4 1 0.314559 -0.350887 0.272537 11.00000 0.01845 0.01814 = 0.01767 -0.00296 -0.00224 -0.00464 C5 1 0.233394 -0.510582 0.405971 11.00000 0.02709 0.01934 = 0.02626 0.00667 -0.00110 -0.00153 AFIX 137 H5A 2 0.229348 -0.599679 0.372560 11.00000 -1.50000 H5B 2 0.145560 -0.496816 0.462262 11.00000 -1.50000 H5C 2 0.353347 -0.529515 0.423812 11.00000 -1.50000 AFIX 0 C6 1 0.015709 -0.262512 0.359958 11.00000 0.01998 0.02125 = 0.01038 0.00323 -0.00133 -0.00286 C7 1 -0.132951 -0.315261 0.360618 11.00000 0.02495 0.01620 = 0.01816 0.00154 -0.00212 -0.00382 AFIX 43 H7 2 -0.117904 -0.422612 0.353483 11.00000 -1.20000 AFIX 0 C8 1 -0.303537 -0.211263 0.371693 11.00000 0.02248 0.02434 = 0.01992 0.00229 -0.00298 -0.00755 AFIX 43 H8 2 -0.405107 -0.248071 0.373775 11.00000 -1.20000 AFIX 0 C9 1 -0.326125 -0.053556 0.379737 11.00000 0.01885 0.02459 = 0.01396 0.00347 0.00048 -0.00246 C10 1 -0.177117 -0.000566 0.381806 11.00000 0.02603 0.01682 = 0.01360 0.00226 -0.00345 -0.00425 C11 1 -0.006645 -0.106082 0.374319 11.00000 0.01992 0.02182 = 0.01459 0.00216 -0.00262 -0.00547 AFIX 43 H11 2 0.094311 -0.071538 0.378988 11.00000 -1.20000 AFIX 0 C12 1 -0.157486 0.258542 0.210393 11.00000 0.02327 0.01829 = 0.02193 0.00078 0.00023 -0.00597 C13 1 -0.171407 0.380447 0.049428 11.00000 0.03488 0.03818 = 0.01984 -0.00271 0.00000 -0.02345 C14 1 -0.208213 0.534690 -0.083261 11.00000 0.04155 0.04111 = 0.03334 -0.00230 -0.00747 -0.02288 C15 1 0.004657 0.307500 -0.084874 11.00000 0.02559 0.03301 = 0.03344 -0.00843 0.00106 -0.01276 C16 1 -0.309613 0.683547 -0.131105 11.00000 0.04541 0.02870 = 0.02579 0.00743 -0.01132 -0.01540 AFIX 137 H16A 2 -0.435163 0.713013 -0.103214 11.00000 -1.50000 H16B 2 -0.302467 0.667271 -0.197889 11.00000 -1.50000 H16C 2 -0.256918 0.766818 -0.123213 11.00000 -1.50000 AFIX 0 C17 1 0.213589 0.060506 -0.086978 11.00000 0.03481 0.02828 = 0.03100 -0.00502 0.00573 -0.00801 AFIX 137 H17A 2 0.274298 0.078020 -0.036195 11.00000 -1.50000 H17B 2 0.300542 -0.008044 -0.132025 11.00000 -1.50000 H17C 2 0.120267 0.011649 -0.061236 11.00000 -1.50000 AFIX 0 HKLF 4 REM shelxl in P-1 REM wR2 = 0.1597, GooF = S = 1.058, Restrained GooF = 1.060 for all data REM R1 = 0.0570 for 2857 Fo > 4sig(Fo) and 0.0676 for all 3424 data REM 274 parameters refined using 3 restraints END WGHT 0.0764 1.5730 REM Instructions for potential hydrogen bonds HTAB N2 Cl1 EQIV $2 x-1, y+1, z HTAB N3 O1_$2 HTAB C3 O4 HTAB C5 Cl1_$1 EQIV $3 -x, -y+1, -z HTAB C16 O4_$3 REM Highest difference peak 1.674, deepest hole -0.588, 1-sigma level 0.081 Q1 1 -0.1810 0.5663 -0.1580 11.00000 0.05 1.67 Q2 1 0.0627 0.2117 -0.0615 11.00000 0.05 1.01 Q3 1 0.0161 0.3338 -0.1361 11.00000 0.05 0.80 Q4 1 0.0172 0.1868 0.0349 11.00000 0.05 0.69 Q5 1 -0.3627 0.3790 0.3031 11.00000 0.05 0.57 Q6 1 -0.1649 0.4376 -0.0052 11.00000 0.05 0.53 Q7 1 -0.1290 0.4412 -0.0844 11.00000 0.05 0.39 Q8 1 -0.0612 0.3082 0.0171 11.00000 0.05 0.29 Q9 1 -0.2061 0.7204 -0.1870 11.00000 0.05 0.26 Q10 1 -0.3745 0.7628 -0.0836 11.00000 0.05 0.24 Q11 1 -0.4066 0.6608 -0.1694 11.00000 0.05 0.23 Q12 1 0.5141 -0.5055 0.2919 11.00000 0.05 0.22 Q13 1 0.1242 -0.5545 0.4413 11.00000 0.05 0.22 Q14 1 0.0646 0.0740 0.3218 11.00000 0.05 0.21 Q15 1 -0.4686 -0.3735 0.4023 11.00000 0.05 0.21 Q16 1 -0.0836 0.4748 0.1134 11.00000 0.05 0.20 Q17 1 0.0380 0.1062 0.2424 11.00000 0.05 0.20 Q18 1 -0.5330 -0.0014 0.2960 11.00000 0.05 0.19 Q19 1 0.1383 -0.0452 0.3387 11.00000 0.05 0.19 Q20 1 0.1171 0.1670 0.3651 11.00000 0.05 0.19 ; _shelx_res_checksum 58390 _olex2_submission_special_instructions 'No special instructions were received' 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.19144(11) 0.19752(9) 0.39516(5) 0.0214(2) Uani 1 1 d . . . . . Cl1 Cl -0.54157(11) 0.07242(10) 0.38275(6) 0.0282(3) Uani 1 1 d . . . . . O1 O 0.4658(3) -0.4478(3) 0.26174(16) 0.0243(5) Uani 1 1 d . . . . . O2 O -0.3327(3) 0.2632(3) 0.46713(16) 0.0298(6) Uani 1 1 d . . . . . O3 O -0.0144(3) 0.2051(3) 0.40020(18) 0.0293(6) Uani 1 1 d . . . . . O4 O -0.0233(3) 0.1511(3) 0.19816(17) 0.0304(6) Uani 1 1 d . . . . . O5 O 0.1353(4) 0.2045(3) -0.1323(2) 0.0408(7) Uani 1 1 d . . . . . N1 N 0.1913(3) -0.3692(3) 0.34490(18) 0.0189(6) Uani 1 1 d . . . . . N2 N -0.2607(4) 0.2893(3) 0.29801(19) 0.0227(6) Uani 1 1 d . . . . . H2 H -0.370232 0.286729 0.294737 0.027 Uiso 1 1 d R . . . . N3 N -0.2324(4) 0.3666(3) 0.14328(19) 0.0249(6) Uani 1 1 d . . . . . H3 H -0.333017 0.436364 0.163097 0.030 Uiso 1 1 calc R . . . . N4 N -0.2621(5) 0.5127(4) 0.0067(2) 0.0334(7) Uani 1 1 d . . . . . N5 N -0.0733(4) 0.4361(4) -0.1304(2) 0.0373(8) Uani 1 1 d . U . . . N6 N -0.0372(4) 0.2682(4) 0.0091(2) 0.0330(7) Uani 1 1 d . U . . . C1 C 0.3732(5) -0.2145(4) 0.1124(2) 0.0287(8) Uani 1 1 d . . . . . H1A H 0.469091 -0.310877 0.094788 0.034 Uiso 1 1 calc R . . . . H1B H 0.308915 -0.157807 0.060280 0.034 Uiso 1 1 calc R . . . . C2 C 0.4013(5) -0.1212(4) 0.1851(3) 0.0338(9) Uani 1 1 d . . . . . H2A H 0.354495 -0.006420 0.178407 0.041 Uiso 1 1 calc R . . . . H2B H 0.514701 -0.159519 0.212922 0.041 Uiso 1 1 calc R . . . . C3 C 0.2672(4) -0.2130(4) 0.2080(2) 0.0222(7) Uani 1 1 d . . . . . H3A H 0.138022 -0.151621 0.213253 0.027 Uiso 1 1 calc R . . . . C4 C 0.3146(4) -0.3509(4) 0.2725(2) 0.0181(7) Uani 1 1 d . . . . . C5 C 0.2334(5) -0.5106(4) 0.4060(2) 0.0260(8) Uani 1 1 d . . . . . H5A H 0.229348 -0.599679 0.372560 0.039 Uiso 1 1 calc GR . . . . H5B H 0.145560 -0.496816 0.462262 0.039 Uiso 1 1 calc GR . . . . H5C H 0.353347 -0.529515 0.423812 0.039 Uiso 1 1 calc GR . . . . C6 C 0.0157(4) -0.2625(4) 0.3600(2) 0.0182(7) Uani 1 1 d . . . . . C7 C -0.1330(4) -0.3153(4) 0.3606(2) 0.0204(7) Uani 1 1 d . . . . . H7 H -0.117904 -0.422612 0.353483 0.025 Uiso 1 1 calc R . . . . C8 C -0.3035(4) -0.2113(4) 0.3717(2) 0.0222(7) Uani 1 1 d . . . . . H8 H -0.405107 -0.248071 0.373775 0.027 Uiso 1 1 calc R . . . . C9 C -0.3261(4) -0.0536(4) 0.3797(2) 0.0205(7) Uani 1 1 d . . . . . C10 C -0.1771(4) -0.0006(4) 0.3818(2) 0.0193(7) Uani 1 1 d . . . . . C11 C -0.0066(4) -0.1061(4) 0.3743(2) 0.0190(7) Uani 1 1 d . . . . . H11 H 0.094311 -0.071538 0.378988 0.023 Uiso 1 1 calc R . . . . C12 C -0.1575(4) 0.2585(4) 0.2104(2) 0.0216(7) Uani 1 1 d . . . . . C13 C -0.1714(5) 0.3804(4) 0.0494(2) 0.0284(8) Uani 1 1 d . . . . . C14 C -0.2082(5) 0.5347(5) -0.0833(3) 0.0359(9) Uani 1 1 d . . . . . C15 C 0.0047(5) 0.3075(4) -0.0849(3) 0.0298(7) Uani 1 1 d . U . . . C16 C -0.3096(5) 0.6835(4) -0.1311(3) 0.0321(8) Uani 1 1 d . . . . . H16A H -0.435163 0.713013 -0.103214 0.048 Uiso 1 1 calc GR . . . . H16B H -0.302467 0.667271 -0.197889 0.048 Uiso 1 1 calc GR . . . . H16C H -0.256918 0.766818 -0.123213 0.048 Uiso 1 1 calc GR . . . . C17 C 0.2136(5) 0.0605(4) -0.0870(3) 0.0324(8) Uani 1 1 d . . . . . H17A H 0.274298 0.078020 -0.036195 0.049 Uiso 1 1 calc GR . . . . H17B H 0.300542 -0.008044 -0.132025 0.049 Uiso 1 1 calc GR . . . . H17C H 0.120267 0.011649 -0.061236 0.049 Uiso 1 1 calc GR . . . . 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 0.0277(5) 0.0159(4) 0.0184(4) -0.0002(3) -0.0048(3) -0.0023(3) Cl1 0.0210(4) 0.0272(5) 0.0302(5) -0.0006(3) -0.0024(3) 0.0017(3) O1 0.0209(12) 0.0199(12) 0.0262(13) 0.0040(9) -0.0002(9) 0.0005(10) O2 0.0407(15) 0.0223(12) 0.0197(12) -0.0039(10) 0.0008(10) -0.0006(11) O3 0.0311(14) 0.0222(13) 0.0364(14) -0.0021(10) -0.0124(11) -0.0067(11) O4 0.0259(13) 0.0269(13) 0.0305(14) -0.0007(10) 0.0029(10) 0.0014(11) O5 0.0407(16) 0.0409(16) 0.0371(16) -0.0008(13) -0.0022(13) -0.0075(13) N1 0.0215(14) 0.0145(13) 0.0187(14) 0.0033(10) -0.0038(11) -0.0025(11) N2 0.0232(14) 0.0216(14) 0.0193(14) 0.0043(11) -0.0010(11) -0.0027(12) N3 0.0273(15) 0.0254(15) 0.0190(15) 0.0015(11) -0.0005(12) -0.0050(12) N4 0.048(2) 0.0361(18) 0.0239(16) 0.0107(13) -0.0121(14) -0.0240(16) N5 0.0397(19) 0.0390(17) 0.0412(19) 0.0017(13) -0.0121(15) -0.0213(15) N6 0.0308(17) 0.0446(19) 0.0291(13) -0.0092(13) 0.0006(13) -0.0192(15) C1 0.0277(19) 0.0303(19) 0.0257(19) 0.0081(15) -0.0015(15) -0.0080(15) C2 0.039(2) 0.028(2) 0.040(2) 0.0108(16) -0.0115(17) -0.0176(17) C3 0.0216(17) 0.0205(17) 0.0220(17) 0.0033(13) -0.0037(13) -0.0029(13) C4 0.0185(16) 0.0181(16) 0.0177(16) -0.0030(12) -0.0022(12) -0.0046(13) C5 0.0271(18) 0.0193(17) 0.0263(18) 0.0067(14) -0.0011(14) -0.0015(14) C6 0.0200(16) 0.0213(16) 0.0104(15) 0.0032(12) -0.0013(12) -0.0029(13) C7 0.0249(17) 0.0162(16) 0.0182(16) 0.0015(12) -0.0021(13) -0.0038(13) C8 0.0225(17) 0.0243(17) 0.0199(17) 0.0023(13) -0.0030(13) -0.0076(14) C9 0.0188(16) 0.0246(17) 0.0140(15) 0.0035(12) 0.0005(12) -0.0025(13) C10 0.0260(17) 0.0168(16) 0.0136(15) 0.0023(12) -0.0034(12) -0.0042(13) C11 0.0199(16) 0.0218(16) 0.0146(15) 0.0022(12) -0.0026(12) -0.0055(13) C12 0.0233(17) 0.0183(16) 0.0219(17) 0.0008(13) 0.0002(13) -0.0060(14) C13 0.035(2) 0.038(2) 0.0198(18) -0.0027(15) 0.0000(15) -0.0234(17) C14 0.042(2) 0.041(2) 0.033(2) -0.0023(17) -0.0075(18) -0.0229(19) C15 0.0256(18) 0.0330(17) 0.0334(14) -0.0084(13) 0.0011(14) -0.0128(15) C16 0.045(2) 0.0287(19) 0.0258(19) 0.0074(15) -0.0113(16) -0.0154(17) C17 0.035(2) 0.0283(19) 0.031(2) -0.0050(15) 0.0057(16) -0.0080(16) 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' Cl Cl 0.1484 0.1585 '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 O2 S1 O3 119.53(15) . . ? O2 S1 N2 104.41(14) . . ? O2 S1 C10 110.34(15) . . ? O3 S1 N2 109.11(15) . . ? O3 S1 C10 107.49(15) . . ? N2 S1 C10 105.05(15) . . ? C15 O5 C17 118.4(3) . . ? C4 N1 C5 119.0(3) . . ? C4 N1 C6 122.6(3) . . ? C6 N1 C5 118.2(3) . . ? S1 N2 H2 109.8 . . ? C12 N2 S1 122.2(2) . . ? C12 N2 H2 109.7 . . ? C12 N3 H3 115.5 . . ? C13 N3 H3 115.5 . . ? C13 N3 C12 129.1(3) . . ? C14 N4 C13 116.7(4) . . ? C14 N5 C15 116.4(4) . . ? C13 N6 C15 110.7(3) . . ? H1A C1 H1B 114.8 . . ? C2 C1 H1A 117.7 . . ? C2 C1 H1B 117.7 . . ? C2 C1 C3 60.8(2) . . ? C3 C1 H1A 117.7 . . ? C3 C1 H1B 117.7 . . ? C1 C2 H2A 117.7 . . ? C1 C2 H2B 117.7 . . ? C1 C2 C3 60.5(2) . . ? H2A C2 H2B 114.8 . . ? C3 C2 H2A 117.7 . . ? C3 C2 H2B 117.7 . . ? C1 C3 C2 58.6(2) . . ? C1 C3 H3A 116.5 . . ? C2 C3 H3A 116.5 . . ? C4 C3 C1 119.4(3) . . ? C4 C3 C2 117.0(3) . . ? C4 C3 H3A 116.5 . . ? O1 C4 N1 120.4(3) . . ? O1 C4 C3 120.9(3) . . ? N1 C4 C3 118.7(3) . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5B 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 N1 119.8(3) . . ? C7 C6 C11 120.0(3) . . ? C11 C6 N1 120.3(3) . . ? C6 C7 H7 120.0 . . ? C8 C7 C6 120.1(3) . . ? C8 C7 H7 120.0 . . ? C7 C8 H8 119.9 . . ? C7 C8 C9 120.2(3) . . ? C9 C8 H8 119.9 . . ? C8 C9 Cl1 117.8(3) . . ? C8 C9 C10 119.9(3) . . ? C10 C9 Cl1 122.3(3) . . ? C9 C10 S1 123.5(2) . . ? C11 C10 S1 116.7(2) . . ? C11 C10 C9 119.7(3) . . ? C6 C11 H11 120.0 . . ? C10 C11 C6 119.9(3) . . ? C10 C11 H11 120.0 . . ? O4 C12 N2 123.0(3) . . ? O4 C12 N3 126.5(3) . . ? N3 C12 N2 110.5(3) . . ? N4 C13 N3 113.6(3) . . ? N6 C13 N3 120.3(3) . . ? N6 C13 N4 126.0(3) . . ? N4 C14 C16 116.7(4) . . ? N5 C14 N4 123.4(4) . . ? N5 C14 C16 119.9(4) . . ? O5 C15 N6 116.3(3) . . ? N5 C15 O5 117.1(4) . . ? N5 C15 N6 126.7(4) . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O5 C17 H17A 109.5 . . ? O5 C17 H17B 109.5 . . ? O5 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 O2 1.431(3) . ? S1 O3 1.431(3) . ? S1 N2 1.650(3) . ? S1 C10 1.777(3) . ? Cl1 C9 1.738(3) . ? O1 C4 1.249(4) . ? O4 C12 1.206(4) . ? O5 C15 1.313(5) . ? O5 C17 1.412(5) . ? N1 C4 1.357(4) . ? N1 C5 1.470(4) . ? N1 C6 1.431(4) . ? N2 H2 0.8799 . ? N2 C12 1.403(4) . ? N3 H3 0.8800 . ? N3 C12 1.382(4) . ? N3 C13 1.381(4) . ? N4 C13 1.347(5) . ? N4 C14 1.327(5) . ? N5 C14 1.309(5) . ? N5 C15 1.312(5) . ? N6 C13 1.328(5) . ? N6 C15 1.394(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C2 1.479(5) . ? C1 C3 1.508(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.512(5) . ? C3 H3A 1.0000 . ? C3 C4 1.479(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.389(5) . ? C6 C11 1.395(5) . ? C7 H7 0.9500 . ? C7 C8 1.389(5) . ? C8 H8 0.9500 . ? C8 C9 1.389(5) . ? C9 C10 1.399(5) . ? C10 C11 1.393(5) . ? C11 H11 0.9500 . ? C14 C16 1.512(5) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 C3 H3A O4 1.00 2.65 3.401(4) 132.2 . yes C5 H5A Cl1 0.98 2.97 3.664(4) 128.5 1_645 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 N2 C12 O4 9.6(5) . . . . ? S1 N2 C12 N3 -170.7(2) . . . . ? S1 C10 C11 C6 -177.5(2) . . . . ? Cl1 C9 C10 S1 4.2(4) . . . . ? Cl1 C9 C10 C11 -176.7(2) . . . . ? O2 S1 N2 C12 179.4(3) . . . . ? O2 S1 C10 C9 44.4(3) . . . . ? O2 S1 C10 C11 -134.8(2) . . . . ? O3 S1 N2 C12 50.5(3) . . . . ? O3 S1 C10 C9 176.3(3) . . . . ? O3 S1 C10 C11 -2.9(3) . . . . ? N1 C6 C7 C8 -177.6(3) . . . . ? N1 C6 C11 C10 175.1(3) . . . . ? N2 S1 C10 C9 -67.6(3) . . . . ? N2 S1 C10 C11 113.2(3) . . . . ? C1 C2 C3 C4 109.5(3) . . . . ? C1 C3 C4 O1 20.4(5) . . . . ? C1 C3 C4 N1 -160.6(3) . . . . ? C2 C1 C3 C4 -105.4(3) . . . . ? C2 C3 C4 O1 -47.0(4) . . . . ? C2 C3 C4 N1 132.0(3) . . . . ? C4 N1 C6 C7 120.5(3) . . . . ? C4 N1 C6 C11 -59.7(4) . . . . ? C5 N1 C4 O1 -4.6(4) . . . . ? C5 N1 C4 C3 176.4(3) . . . . ? C5 N1 C6 C7 -54.3(4) . . . . ? C5 N1 C6 C11 125.4(3) . . . . ? C6 N1 C4 O1 -179.4(3) . . . . ? C6 N1 C4 C3 1.6(4) . . . . ? C6 C7 C8 C9 1.7(5) . . . . ? C7 C6 C11 C10 -5.1(5) . . . . ? C7 C8 C9 Cl1 174.3(2) . . . . ? C7 C8 C9 C10 -3.5(5) . . . . ? C8 C9 C10 S1 -178.2(2) . . . . ? C8 C9 C10 C11 1.0(5) . . . . ? C9 C10 C11 C6 3.3(5) . . . . ? C10 S1 N2 C12 -64.4(3) . . . . ? C11 C6 C7 C8 2.7(5) . . . . ? C12 N3 C13 N4 -170.6(3) . . . . ? C12 N3 C13 N6 10.5(5) . . . . ? C13 N3 C12 O4 -2.0(6) . . . . ? C13 N3 C12 N2 178.3(3) . . . . ? C13 N4 C14 N5 -0.6(5) . . . . ? C13 N4 C14 C16 -179.7(3) . . . . ? C13 N6 C15 O5 -179.6(3) . . . . ? C13 N6 C15 N5 0.2(5) . . . . ? C14 N4 C13 N3 178.8(3) . . . . ? C14 N4 C13 N6 -2.3(5) . . . . ? C14 N5 C15 O5 177.1(3) . . . . ? C14 N5 C15 N6 -2.7(5) . . . . ? C15 N5 C14 N4 2.8(5) . . . . ? C15 N5 C14 C16 -178.0(3) . . . . ? C15 N6 C13 N3 -178.8(3) . . . . ? C15 N6 C13 N4 2.4(5) . . . . ? C17 O5 C15 N5 -175.8(3) . . . . ? C17 O5 C15 N6 4.1(5) . . . . ?