#------------------------------------------------------------------------------ #$Date: 2016-08-11 15:44:16 +0300 (Thu, 11 Aug 2016) $ #$Revision: 185754 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119123.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_7119123 loop_ _publ_author_name 'Cory M. Widdifield' 'Harry Robson' 'Paul Hodgkinson' _publ_section_title ; Furosemide's one little hydrogen atom: NMR crystallography structure verification of powdered molecular organics ; _journal_name_full Chem.Commun. _journal_page_first 6685 _journal_volume 52 _journal_year 2016 _chemical_formula_moiety 'C12 H11 Cl N2 O5 S' _chemical_formula_sum 'C12 H11 Cl N2 O5 S' _chemical_formula_weight 330.74 _chemical_name_common Furosemide _chemical_name_systematic ; ? ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2016-02-03 _audit_creation_method ; Olex2 1.2-beta (compiled 2015.11.20 svn.r3248 for OlexSys, GUI svn.r5133) ; _audit_update_record ; 2016-03-07 deposited with the CCDC. 2016-04-18 downloaded from the CCDC. ; _cell_angle_alpha 92.938(5) _cell_angle_beta 107.085(5) _cell_angle_gamma 116.622(6) _cell_formula_units_Z 4 _cell_length_a 9.5347(5) _cell_length_b 10.4694(6) _cell_length_c 15.6057(9) _cell_measurement_reflns_used 2809 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 29.8050 _cell_measurement_theta_min 2.2170 _cell_volume 1300.34(16) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _diffrn_ambient_temperature 120.0 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.1511 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; 1 omega -34.00 44.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 -57.0000 -180.0000 78 2 omega 44.00 81.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 -178.0000 -150.0000 37 3 omega 14.00 68.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 -100.0000 -60.0000 54 4 omega 44.00 71.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 -100.0000 60.0000 27 5 omega 23.00 71.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 -100.0000 -180.0000 48 6 omega 9.00 98.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 57.0000 60.0000 89 7 omega -44.00 67.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 -19.0000 -120.0000 111 8 omega 9.00 98.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 57.0000 -30.0000 89 9 omega 35.00 94.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 178.0000 120.0000 59 10 omega -1.00 99.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 77.0000 -120.0000 100 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0482803000 _diffrn_orient_matrix_UB_12 -0.0335980000 _diffrn_orient_matrix_UB_13 0.0196828000 _diffrn_orient_matrix_UB_21 -0.0228266000 _diffrn_orient_matrix_UB_22 -0.0408962000 _diffrn_orient_matrix_UB_23 -0.0441273000 _diffrn_orient_matrix_UB_31 0.0712004000 _diffrn_orient_matrix_UB_32 0.0567245000 _diffrn_orient_matrix_UB_33 -0.0059058000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0797 _diffrn_reflns_av_unetI/netI 0.1153 _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 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 19564 _diffrn_reflns_theta_full 29.00 _diffrn_reflns_theta_max 29.00 _diffrn_reflns_theta_min 2.23 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.479 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_correction_T_min 0.956 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.508 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.098 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 467 _refine_ls_number_reflns 6913 _refine_ls_number_restraints 43 _refine_ls_restrained_S_all 0.990 _refine_ls_R_factor_all 0.1193 _refine_ls_R_factor_gt 0.0561 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0240P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0935 _refine_ls_wR_factor_ref 0.1209 _reflns_number_gt 3893 _reflns_number_total 6913 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL 16srv043 in P-1 #2 REM reset to P-1 #2 CELL 0.71073 9.534736 10.469428 15.605726 92.9384 107.0845 116.6221 ZERR 4 0.000539 0.000584 0.00094 0.0047 0.0052 0.0056 LATT 1 SFAC C H Cl N O S UNIT 48 44 4 8 20 4 EQIV $1 1-X,1-Y,1-Z EQIV $2 -X,1-Y,1-Z EQIV $3 +X,-1+Y,+Z EQIV $4 -X,2-Y,1-Z SADI 0.005 C10 H10 C11 H11 C12 H12 C12A H12A C11A H11A C10A H10A SADI 0.005 C8 H8a C8 H8b C8A H8Aa C8A H8Ab SADI 0.005 C3 H3 C6 H6 C3A H3A C6A H6A SADI 0.005 N1 H1 N1A H1A N2 H2b N2 H2a N2A H2Ac N2A H2Ab SADI 0.005 O2A H2Aa O2 H2 L.S. 9 PLAN 5 SIZE 0.04 0.13 0.28 CONF C4 C5 S1 O4 CONF C6 C5 S1 O4 CONF C4 C5 S1 O5 CONF C6 C5 S1 O5 CONF C4 C5 S1 N2 CONF C6 C5 S1 N2 CONF C2 C1 C7 O2 CONF C6 C1 C7 O2 CONF C2 C1 C7 O3 CONF C6 C1 C7 O3 CONF C1 C2 N1 C8 CONF C3 C2 N1 C8 CONF C9 C8 N1 C2 CONF N1 C8 C9 O1 CONF C10 C9 C8 N1 CONF C4A C5A S1A O4A CONF C6A C5A S1A O4A CONF C4A C5A S1A O5A CONF C6A C5A S1A O5A CONF C4A C5A S1A N2A CONF C6A C5A S1A N2A CONF C2A C1A C7A O2A CONF C6A C1A C7A O2A CONF C2A C1A C7A O3A CONF C6A C1A C7A O3A CONF C1A C2A N1A C8A CONF C3A C2A N1A C8A CONF C9A C8A N1A C2A CONF N1A C8A C9A O1A CONF C10A C9A C8A N1A HTAB O2 O3A_$1 HTAB N1 O3 HTAB N2 O5_$2 HTAB N2 O5A_$3 HTAB O2A O3_$1 HTAB N1A O3A HTAB N2A O5 HTAB N2A O5A_$4 BOND $h fmap 2 53 acta OMIT -2 58 WGHT 0.024 0 FVAR 2.54148 Cl1 3 0.00525 0.60206 0.19321 11.00000 0.02307 0.02166 0.02312 = 0.00851 0.00646 0.01417 S1 6 -0.12313 0.42881 0.34625 11.00000 0.01625 0.01681 0.02268 = 0.00544 0.00647 0.00925 O1 5 0.25355 0.36876 0.06799 11.00000 0.02211 0.02629 0.03087 = 0.00504 0.00811 0.01197 O2 5 0.34057 0.30813 0.49642 11.00000 0.02174 0.03156 0.02017 = 0.01387 0.00873 0.01647 O3 5 0.49998 0.32425 0.41251 11.00000 0.02179 0.02642 0.02607 = 0.00885 0.00907 0.01565 O4 5 -0.25985 0.36848 0.26014 11.00000 0.01861 0.02381 0.02513 = 0.00523 0.00331 0.01040 O5 5 -0.08460 0.56531 0.39938 11.00000 0.02424 0.01912 0.02780 = 0.00295 0.00896 0.01434 N1 4 0.47319 0.47034 0.27304 11.00000 0.02001 0.02417 0.02101 = 0.00933 0.00869 0.01334 N2 4 -0.16391 0.31232 0.40927 11.00000 0.02397 0.01865 0.02861 = 0.01132 0.01482 0.01086 C1 1 0.29855 0.40800 0.36673 11.00000 0.01421 0.01484 0.01586 = 0.00407 0.00372 0.00466 C2 1 0.34439 0.46929 0.29335 11.00000 0.01483 0.01416 0.01841 = 0.00284 0.00347 0.00467 C3 1 0.24923 0.53065 0.24267 11.00000 0.01970 0.01509 0.01447 = 0.00313 0.00424 0.00770 C4 1 0.11174 0.52246 0.25908 11.00000 0.01663 0.01477 0.01846 = 0.00473 0.00144 0.00825 C5 1 0.05921 0.45289 0.32768 11.00000 0.01776 0.00970 0.02051 = 0.00368 0.00512 0.00657 C6 1 0.15719 0.40106 0.38104 11.00000 0.01831 0.01402 0.01946 = 0.00375 0.00600 0.00781 C7 1 0.38773 0.34339 0.42628 11.00000 0.01638 0.01606 0.01742 = 0.00366 0.00480 0.00618 C8 1 0.51899 0.52144 0.19449 11.00000 0.01737 0.02132 0.02587 = 0.00783 0.01175 0.00702 C9 1 0.42106 0.41024 0.10664 11.00000 0.01742 0.01964 0.02345 = 0.00756 0.00842 0.00716 C10 1 0.46407 0.34181 0.05246 11.00000 0.02945 0.02817 0.03012 = 0.00763 0.01588 0.01304 C11 1 0.31670 0.25273 -0.02590 11.00000 0.04451 0.02541 0.02120 = 0.00339 0.01239 0.01657 C12 1 0.19426 0.27091 -0.01366 11.00000 0.03215 0.02477 0.02694 = 0.00479 0.00429 0.01253 H1 2 0.51494 0.42339 0.30259 11.00000 0.02857 H2 2 0.38235 0.25730 0.53129 11.00000 0.04272 H2a 2 -0.10378 0.34557 0.46503 11.00000 0.05443 H2b 2 -0.19795 0.22580 0.38439 11.00000 0.04803 H3 2 0.28169 0.57429 0.19370 11.00000 0.00971 H6 2 0.13059 0.35134 0.42927 11.00000 0.02662 H8a 2 0.63657 0.54888 0.20898 11.00000 0.01626 H8b 2 0.51258 0.61090 0.18892 11.00000 0.01044 H10 2 0.56801 0.35219 0.06677 11.00000 0.03825 H11 2 0.30543 0.19904 -0.07713 11.00000 0.01998 H12 2 0.08279 0.23692 -0.04065 11.00000 0.02227 Cl1A 3 0.02963 1.10623 0.18112 11.00000 0.02244 0.02277 0.02406 = 0.00950 0.00593 0.01379 S1A 6 -0.09157 0.94038 0.33989 11.00000 0.01571 0.01536 0.02188 = 0.00413 0.00565 0.00813 O1A 5 0.35494 0.75394 0.09595 11.00000 0.02521 0.02131 0.02636 = 0.00757 0.00754 0.01174 O2A 5 0.36143 0.80556 0.48033 11.00000 0.02306 0.03096 0.02638 = 0.01624 0.01194 0.01656 O3A 5 0.53787 0.84363 0.40455 11.00000 0.02193 0.02667 0.02576 = 0.00969 0.00926 0.01532 O4A 5 -0.22816 0.87817 0.25376 11.00000 0.01876 0.02472 0.02203 = 0.00430 0.00208 0.01063 O5A 5 -0.05690 1.07537 0.39275 11.00000 0.02321 0.01630 0.02686 = 0.00440 0.00934 0.01058 N1A 4 0.50432 0.98493 0.26235 11.00000 0.01961 0.02441 0.01664 = 0.00852 0.00655 0.01443 N2A 4 -0.12795 0.82523 0.40350 11.00000 0.02257 0.01740 0.02237 = 0.00629 0.00948 0.01019 C1A 1 0.33017 0.92003 0.35639 11.00000 0.01541 0.01628 0.01918 = 0.00341 0.00608 0.00669 C2A 1 0.37339 0.97996 0.28304 11.00000 0.01741 0.01388 0.01728 = 0.00227 0.00379 0.00744 C3A 1 0.27531 1.03780 0.23065 11.00000 0.01997 0.01982 0.01820 = 0.00748 0.00646 0.00957 C4A 1 0.13907 1.03034 0.24865 11.00000 0.01622 0.01275 0.02123 = 0.00090 0.00252 0.00649 C5A 1 0.09085 0.96486 0.31914 11.00000 0.01738 0.01389 0.01713 = 0.00137 0.00413 0.00672 C6A 1 0.19076 0.91480 0.37214 11.00000 0.01821 0.01733 0.01768 = 0.00317 0.00589 0.00815 C7A 1 0.41822 0.85339 0.41480 11.00000 0.01634 0.01474 0.01747 = 0.00393 0.00498 0.00684 C8A 1 0.52526 1.01113 0.17369 11.00000 0.01789 0.01932 0.02585 = 0.00925 0.01066 0.00789 C9A 1 0.38491 0.89540 0.09405 11.00000 0.02237 0.01812 0.02480 = 0.00825 0.01320 0.01102 C10A 1 0.27312 0.89409 0.01800 11.00000 0.03529 0.02352 0.02668 = 0.00458 0.00030 0.01690 C11A 1 0.16812 0.74654 -0.03134 11.00000 0.03231 0.02902 0.03087 = 0.00654 0.00325 0.01909 C12A 1 0.22020 0.66632 0.01799 11.00000 0.02366 0.02454 0.02696 = 0.00454 0.00882 0.01037 H1A 2 0.55248 0.94008 0.28891 11.00000 0.01749 H8Aa 2 0.63107 1.01583 0.17724 11.00000 0.02732 H2Aa 2 0.41140 0.75974 0.51510 11.00000 0.07211 H2Ab 2 -0.07704 0.85393 0.46043 11.00000 0.01970 H2Ac 2 -0.14701 0.74031 0.38516 11.00000 0.03211 H3A 2 0.28793 1.07342 0.17595 11.00000 0.02682 H6A 2 0.16460 0.87222 0.42271 11.00000 0.02625 H8Ab 2 0.53473 1.10557 0.16513 11.00000 0.02187 H10A 2 0.26309 0.97278 0.00365 11.00000 0.05243 H11A 2 0.08209 0.71291 -0.08555 11.00000 0.04626 H12A 2 0.18365 0.56964 0.01461 11.00000 0.05988 HKLF 4 END ; _cod_data_source_file c6cc02171a2.cif _cod_data_source_block fur_new_16srv043 _cod_original_cell_volume 1300.35(13) _cod_database_code 7119123 _chemical_oxdiff_formula 'C12 H11 Cl1 N2 O5 S1' _reflns_odcompleteness_completeness 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.44 _olex2_refinement_description ; 1. Restrained distances C10-H10 \\sim C11-H11 \\sim C12-H12 \\sim C12A-H12A \\sim C11A-H11A \\sim C10A-H10A with sigma of 0.005 C8-H8A \\sim C8-H8B \\sim C8A-H8AA \\sim C8A-H8AB with sigma of 0.005 C3-H3 \\sim C6-H6 \\sim C3A-H3A \\sim C6A-H6A with sigma of 0.005 N1-H1 \\sim N1A-H1A \\sim N2-H2B \\sim N2-H2A \\sim N2A-H2AC \\sim N2A-H2AB with sigma of 0.005 O2A-H2AA \\sim O2-H2 with sigma of 0.005 ; loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl1 Cl 0.00523(10) 0.60204(9) 0.19321(6) 0.02161(19) Uani 1 d . . . S1 S -0.12313(9) 0.42882(9) 0.34624(6) 0.01822(19) Uani 1 d . . . O1 O 0.2535(3) 0.3688(3) 0.06799(17) 0.0267(6) Uani 1 d . . . O2 O 0.3406(3) 0.3081(3) 0.49644(16) 0.0224(5) Uani 1 d . . D O3 O 0.5000(3) 0.3242(2) 0.41250(15) 0.0228(5) Uani 1 d . . . O4 O -0.2598(3) 0.3685(2) 0.26013(15) 0.0235(5) Uani 1 d . . . O5 O -0.0846(3) 0.5653(2) 0.39940(16) 0.0223(5) Uani 1 d . . . N1 N 0.4732(3) 0.4703(3) 0.2730(2) 0.0201(6) Uani 1 d . . D N2 N -0.1639(4) 0.3123(3) 0.4093(2) 0.0219(7) Uani 1 d . . D C1 C 0.2985(4) 0.4080(3) 0.3667(2) 0.0162(7) Uani 1 d . . . C2 C 0.3444(4) 0.4693(3) 0.2934(2) 0.0174(7) Uani 1 d . . . C3 C 0.2492(4) 0.5306(3) 0.2427(2) 0.0171(7) Uani 1 d . . D C4 C 0.1117(4) 0.5224(3) 0.2590(2) 0.0174(7) Uani 1 d . . . C5 C 0.0592(4) 0.4529(3) 0.3277(2) 0.0163(7) Uani 1 d . . . C6 C 0.1572(4) 0.4011(3) 0.3810(2) 0.0173(7) Uani 1 d . . D C7 C 0.3877(4) 0.3434(3) 0.4263(2) 0.0175(7) Uani 1 d . . . C8 C 0.5189(4) 0.5213(4) 0.1944(2) 0.0213(7) Uani 1 d . . D C9 C 0.4211(4) 0.4102(4) 0.1066(2) 0.0203(7) Uani 1 d . . . C10 C 0.4639(5) 0.3418(4) 0.0525(3) 0.0282(8) Uani 1 d . . D C11 C 0.3167(5) 0.2528(4) -0.0258(3) 0.0303(9) Uani 1 d . . D C12 C 0.1944(5) 0.2710(4) -0.0136(3) 0.0301(9) Uani 1 d . . D H1 H 0.516(4) 0.424(3) 0.303(2) 0.030(11) Uiso 1 d . . D H2 H 0.383(4) 0.258(4) 0.531(2) 0.042(12) Uiso 1 d . . D H2A H -0.103(4) 0.345(4) 0.4652(12) 0.056(15) Uiso 1 d . . D H2B H -0.198(4) 0.225(2) 0.385(2) 0.045(13) Uiso 1 d . . D H3 H 0.281(3) 0.574(3) 0.1938(16) 0.010(8) Uiso 1 d . . D H6 H 0.130(4) 0.352(3) 0.4292(17) 0.025(9) Uiso 1 d . . D H8A H 0.637(2) 0.548(3) 0.209(2) 0.017(8) Uiso 1 d . . D H8B H 0.512(3) 0.611(2) 0.189(2) 0.011(8) Uiso 1 d . . D H10 H 0.567(3) 0.351(4) 0.067(2) 0.038(11) Uiso 1 d . . D H11 H 0.306(4) 0.199(3) -0.0767(15) 0.021(9) Uiso 1 d . . D H12 H 0.083(2) 0.237(3) -0.040(2) 0.022(9) Uiso 1 d . . D Cl1A Cl 0.02964(9) 1.10622(9) 0.18112(6) 0.0224(2) Uani 1 d . . . S1A S -0.09157(9) 0.94039(9) 0.33989(6) 0.01773(19) Uani 1 d . . . O1A O 0.3549(3) 0.7539(2) 0.09592(16) 0.0244(5) Uani 1 d . . . O2A O 0.3614(3) 0.8055(3) 0.48035(17) 0.0242(6) Uani 1 d . . D O3A O 0.5379(3) 0.8436(2) 0.40454(15) 0.0229(5) Uani 1 d . . . O4A O -0.2282(3) 0.8782(2) 0.25373(15) 0.0231(5) Uani 1 d . . . O5A O -0.0569(3) 1.0754(2) 0.39279(15) 0.0216(5) Uani 1 d . . . N1A N 0.5043(3) 0.9849(3) 0.26234(19) 0.0185(6) Uani 1 d . . D N2A N -0.1280(4) 0.8252(3) 0.4035(2) 0.0202(6) Uani 1 d . . D C1A C 0.3301(4) 0.9200(3) 0.3564(2) 0.0172(7) Uani 1 d . . . C2A C 0.3733(4) 0.9799(3) 0.2830(2) 0.0169(7) Uani 1 d . . . C3A C 0.2753(4) 1.0378(4) 0.2307(2) 0.0192(7) Uani 1 d . . D C4A C 0.1391(4) 1.0303(3) 0.2486(2) 0.0180(7) Uani 1 d . . . C5A C 0.0908(4) 0.9648(3) 0.3191(2) 0.0169(7) Uani 1 d . . . C6A C 0.1909(4) 0.9149(3) 0.3721(2) 0.0179(7) Uani 1 d . . D C7A C 0.4182(4) 0.8534(3) 0.4148(2) 0.0167(7) Uani 1 d . . . C8A C 0.5252(4) 1.0111(4) 0.1737(2) 0.0205(7) Uani 1 d . . D C9A C 0.3850(4) 0.8954(3) 0.0941(2) 0.0198(7) Uani 1 d . . . C10A C 0.2731(5) 0.8940(4) 0.0180(3) 0.0302(9) Uani 1 d . . D C11A C 0.1683(5) 0.7466(4) -0.0313(3) 0.0310(9) Uani 1 d . . D C12A C 0.2203(4) 0.6664(4) 0.0180(3) 0.0256(8) Uani 1 d . . D H1A H 0.553(3) 0.941(3) 0.289(2) 0.017(9) Uiso 1 d . . D H8AA H 0.632(3) 1.016(4) 0.178(2) 0.027(9) Uiso 1 d . . D H2AA H 0.411(5) 0.759(5) 0.515(3) 0.072(16) Uiso 1 d . . D H2AB H -0.076(3) 0.854(4) 0.4606(10) 0.023(10) Uiso 1 d . . D H2AC H -0.147(4) 0.740(2) 0.386(2) 0.032(11) Uiso 1 d . . D H3A H 0.287(4) 1.073(3) 0.1760(16) 0.027(10) Uiso 1 d . . D H6A H 0.165(4) 0.873(3) 0.4228(17) 0.025(9) Uiso 1 d . . D H8AB H 0.535(4) 1.106(2) 0.165(2) 0.022(9) Uiso 1 d . . D H10A H 0.262(5) 0.972(3) 0.004(3) 0.050(13) Uiso 1 d . . D H11A H 0.083(3) 0.713(4) -0.0854(15) 0.046(12) Uiso 1 d . . D H12A H 0.185(5) 0.5700(19) 0.014(3) 0.059(14) Uiso 1 d . . 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 Cl1 0.0232(4) 0.0217(4) 0.0232(5) 0.0085(4) 0.0065(3) 0.0142(3) S1 0.0164(4) 0.0169(4) 0.0228(5) 0.0055(4) 0.0065(4) 0.0093(3) O1 0.0222(12) 0.0262(14) 0.0309(15) 0.0050(12) 0.0082(11) 0.0119(11) O2 0.0218(12) 0.0315(14) 0.0201(14) 0.0139(12) 0.0086(11) 0.0165(11) O3 0.0219(11) 0.0264(13) 0.0259(14) 0.0088(11) 0.0091(11) 0.0157(10) O4 0.0186(11) 0.0240(13) 0.0249(14) 0.0054(11) 0.0033(10) 0.0104(10) O5 0.0246(12) 0.0190(12) 0.0277(14) 0.0030(11) 0.0091(11) 0.0145(10) N1 0.0201(14) 0.0242(16) 0.0210(17) 0.0094(14) 0.0087(13) 0.0134(12) N2 0.0240(15) 0.0186(16) 0.029(2) 0.0116(15) 0.0150(15) 0.0108(13) C1 0.0141(14) 0.0147(16) 0.0158(17) 0.0041(14) 0.0037(13) 0.0046(12) C2 0.0147(14) 0.0142(16) 0.0185(18) 0.0028(14) 0.0035(13) 0.0046(12) C3 0.0197(16) 0.0151(16) 0.0142(17) 0.0032(14) 0.0043(14) 0.0077(13) C4 0.0165(15) 0.0145(16) 0.0185(18) 0.0046(14) 0.0013(14) 0.0081(13) C5 0.0176(15) 0.0097(15) 0.0204(18) 0.0036(14) 0.0051(14) 0.0066(12) C6 0.0184(15) 0.0139(16) 0.0191(18) 0.0037(14) 0.0060(14) 0.0077(13) C7 0.0164(15) 0.0160(16) 0.0173(18) 0.0036(14) 0.0049(14) 0.0062(13) C8 0.0175(16) 0.0214(18) 0.026(2) 0.0079(16) 0.0118(15) 0.0072(14) C9 0.0174(15) 0.0194(17) 0.0234(19) 0.0078(15) 0.0084(14) 0.0072(14) C10 0.029(2) 0.028(2) 0.030(2) 0.0076(18) 0.0159(18) 0.0130(17) C11 0.045(2) 0.025(2) 0.021(2) 0.0033(17) 0.0123(19) 0.0167(18) C12 0.032(2) 0.025(2) 0.027(2) 0.0049(17) 0.0041(18) 0.0123(17) Cl1A 0.0225(4) 0.0228(4) 0.0241(5) 0.0095(4) 0.0059(4) 0.0138(3) S1A 0.0158(4) 0.0154(4) 0.0220(5) 0.0042(4) 0.0057(3) 0.0082(3) O1A 0.0252(12) 0.0213(13) 0.0264(14) 0.0074(11) 0.0074(11) 0.0118(10) O2A 0.0231(12) 0.0311(14) 0.0264(15) 0.0164(12) 0.0120(11) 0.0167(11) O3A 0.0219(11) 0.0266(13) 0.0258(14) 0.0097(11) 0.0093(11) 0.0154(10) O4A 0.0186(11) 0.0248(13) 0.0218(13) 0.0044(11) 0.0019(10) 0.0105(10) O5A 0.0234(11) 0.0162(12) 0.0269(14) 0.0044(11) 0.0095(11) 0.0107(10) N1A 0.0196(13) 0.0243(16) 0.0168(16) 0.0086(13) 0.0066(12) 0.0144(12) N2A 0.0228(14) 0.0173(16) 0.0226(18) 0.0067(14) 0.0097(14) 0.0103(13) C1A 0.0153(14) 0.0162(16) 0.0190(18) 0.0034(14) 0.0059(14) 0.0067(13) C2A 0.0172(15) 0.0139(16) 0.0174(18) 0.0023(14) 0.0038(14) 0.0073(13) C3A 0.0198(16) 0.0198(17) 0.0180(19) 0.0075(15) 0.0063(14) 0.0094(14) C4A 0.0161(15) 0.0127(16) 0.0211(18) 0.0009(14) 0.0025(14) 0.0065(13) C5A 0.0173(15) 0.0138(16) 0.0169(18) 0.0013(14) 0.0041(14) 0.0067(13) C6A 0.0183(15) 0.0172(17) 0.0174(18) 0.0033(14) 0.0060(14) 0.0081(13) C7A 0.0164(15) 0.0147(16) 0.0173(18) 0.0039(14) 0.0051(14) 0.0067(13) C8A 0.0180(16) 0.0196(18) 0.026(2) 0.0094(16) 0.0108(15) 0.0081(14) C9A 0.0225(16) 0.0180(17) 0.025(2) 0.0084(15) 0.0132(15) 0.0112(14) C10A 0.035(2) 0.024(2) 0.027(2) 0.0045(18) 0.0004(17) 0.0169(17) C11A 0.032(2) 0.029(2) 0.031(2) 0.0064(19) 0.0030(18) 0.0189(17) C12A 0.0237(17) 0.024(2) 0.027(2) 0.0043(17) 0.0087(16) 0.0104(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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 -1 1 0.0836 0.0000 -1.0000 1.0000 0.0533 -0.0032 -0.0626 0 1 -1 0.0836 -0.0000 1.0000 -1.0000 -0.0533 0.0032 0.0626 0 0 -1 0.0213 -0.0000 0.0000 -1.0000 -0.0197 0.0441 0.0059 0 0 1 0.0213 0.0000 -0.0000 1.0000 0.0197 -0.0441 -0.0059 1 0 -1 0.0610 1.0000 0.0000 -1.0000 0.0286 0.0213 0.0771 -1 0 1 0.0610 -1.0000 -0.0000 1.0000 -0.0286 -0.0213 -0.0771 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 O4 S1 O5 117.90(14) . . O4 S1 N2 107.80(16) . . O4 S1 C5 108.89(14) . . O5 S1 N2 106.45(15) . . O5 S1 C5 107.83(13) . . N2 S1 C5 107.54(15) . . C9 O1 C12 105.7(3) . . C7 O2 H2 117(2) . . C2 N1 C8 124.7(3) . . C2 N1 H1 114(2) . . C8 N1 H1 120(2) . . S1 N2 H2A 115(3) . . S1 N2 H2B 117(3) . . H2A N2 H2B 120(4) . . C2 C1 C7 123.1(3) . . C6 C1 C2 119.5(3) . . C6 C1 C7 117.4(3) . . N1 C2 C1 121.9(3) . . N1 C2 C3 121.2(3) . . C3 C2 C1 116.9(3) . . C2 C3 H3 117.3(17) . . C4 C3 C2 121.8(3) . . C4 C3 H3 120.9(17) . . C3 C4 Cl1 117.8(2) . . C3 C4 C5 121.3(3) . . C5 C4 Cl1 120.9(2) . . C4 C5 S1 123.1(2) . . C6 C5 S1 119.7(2) . . C6 C5 C4 117.2(3) . . C1 C6 H6 114.1(19) . . C5 C6 C1 123.1(3) . . C5 C6 H6 122.8(19) . . O2 C7 C1 114.4(3) . . O3 C7 O2 122.2(3) . . O3 C7 C1 123.4(3) . . N1 C8 C9 114.5(3) . . N1 C8 H8A 107.5(18) . . N1 C8 H8B 109.1(17) . . C9 C8 H8A 107.4(18) . . C9 C8 H8B 111.8(18) . . H8A C8 H8B 106(2) . . O1 C9 C8 117.1(3) . . C10 C9 O1 110.0(3) . . C10 C9 C8 132.8(3) . . C9 C10 C11 107.0(3) . . C9 C10 H10 124(2) . . C11 C10 H10 129(2) . . C10 C11 H11 129(2) . . C12 C11 C10 106.6(3) . . C12 C11 H11 125(2) . . O1 C12 H12 109(2) . . C11 C12 O1 110.7(3) . . C11 C12 H12 140(2) . . O4A S1A O5A 117.90(14) . . O4A S1A N2A 108.23(15) . . O4A S1A C5A 107.66(14) . . O5A S1A N2A 106.09(15) . . O5A S1A C5A 109.34(13) . . N2A S1A C5A 107.15(15) . . C12A O1A C9A 106.5(3) . . C7A O2A H2AA 115(3) . . C2A N1A C8A 122.8(3) . . C2A N1A H1A 119(2) . . C8A N1A H1A 114(2) . . S1A N2A H2AB 119(2) . . S1A N2A H2AC 121(2) . . H2AB N2A H2AC 111(3) . . C2A C1A C7A 123.3(3) . . C6A C1A C2A 119.3(3) . . C6A C1A C7A 117.3(3) . . N1A C2A C1A 122.4(3) . . N1A C2A C3A 120.1(3) . . C1A C2A C3A 117.5(3) . . C2A C3A H3A 124(2) . . C4A C3A C2A 121.2(3) . . C4A C3A H3A 113.9(19) . . C3A C4A Cl1A 117.2(2) . . C3A C4A C5A 121.6(3) . . C5A C4A Cl1A 121.2(2) . . C4A C5A S1A 123.5(2) . . C6A C5A S1A 119.6(2) . . C6A C5A C4A 116.9(3) . . C1A C6A H6A 117.2(19) . . C5A C6A C1A 123.4(3) . . C5A C6A H6A 119.3(19) . . O2A C7A C1A 114.4(3) . . O3A C7A O2A 122.0(3) . . O3A C7A C1A 123.6(3) . . N1A C8A C9A 112.8(3) . . N1A C8A H8AA 106.8(19) . . N1A C8A H8AB 110.1(19) . . C9A C8A H8AA 110.7(19) . . C9A C8A H8AB 109(2) . . H8AA C8A H8AB 107(2) . . O1A C9A C8A 116.4(3) . . C10A C9A O1A 108.9(3) . . C10A C9A C8A 134.7(3) . . C9A C10A C11A 107.6(3) . . C9A C10A H10A 125(3) . . C11A C10A H10A 127(3) . . C10A C11A H11A 127(3) . . C12A C11A C10A 106.7(3) . . C12A C11A H11A 126(3) . . O1A C12A H12A 114(3) . . C11A C12A O1A 110.3(3) . . C11A C12A H12A 135(3) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cl1 C4 1.736(3) . S1 O4 1.432(2) . S1 O5 1.447(2) . S1 N2 1.591(3) . S1 C5 1.755(3) . O1 C9 1.375(4) . O1 C12 1.384(4) . O2 C7 1.311(4) . O2 H2 0.91(3) . O3 C7 1.247(3) . N1 C2 1.351(4) . N1 C8 1.467(4) . N1 H1 0.841(14) . N2 H2A 0.842(14) . N2 H2B 0.841(14) . C1 C2 1.425(4) . C1 C6 1.401(4) . C1 C7 1.469(4) . C2 C3 1.419(4) . C3 C4 1.374(4) . C3 H3 0.965(16) . C4 C5 1.413(4) . C5 C6 1.380(4) . C6 H6 0.965(16) . C8 C9 1.488(5) . C8 H8A 0.975(14) . C8 H8B 0.974(14) . C9 C10 1.341(5) . C10 C11 1.427(5) . C10 H10 0.900(14) . C11 C12 1.326(5) . C11 H11 0.901(14) . C12 H12 0.901(14) . Cl1A C4A 1.735(3) . S1A O4A 1.431(2) . S1A O5A 1.446(2) . S1A N2A 1.585(3) . S1A C5A 1.771(3) . O1A C9A 1.381(4) . O1A C12A 1.371(4) . O2A C7A 1.314(4) . O2A H2AA 0.91(3) . O3A C7A 1.244(3) . N1A C2A 1.359(4) . N1A C8A 1.477(4) . N1A H1A 0.842(14) . N2A H2AB 0.842(14) . N2A H2AC 0.842(14) . C1A C2A 1.413(4) . C1A C6A 1.398(4) . C1A C7A 1.471(4) . C2A C3A 1.420(4) . C3A C4A 1.377(4) . C3A H3A 0.965(16) . C4A C5A 1.409(4) . C5A C6A 1.377(4) . C6A H6A 0.965(16) . C8A C9A 1.489(5) . C8A H8AA 0.974(14) . C8A H8AB 0.974(14) . C9A C10A 1.337(5) . C10A C11A 1.421(5) . C10A H10A 0.900(14) . C11A C12A 1.325(5) . C11A H11A 0.901(14) . C12A H12A 0.901(15) . 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 N1 H1 O3 0.841(14) 2.05(2) 2.740(4) 138(3) . O2 H2 O3A 0.91(3) 1.75(3) 2.665(3) 178(4) 2_666 N2 H2A O5 0.842(14) 2.149(16) 2.983(4) 171(4) 2_566 N2 H2B O5A 0.841(14) 2.47(3) 3.101(4) 133(3) 1_545 N1A H1A O3A 0.842(14) 2.12(2) 2.749(3) 131(3) . O2A H2AA O3 0.91(3) 1.72(3) 2.633(3) 176(4) 2_666 N2A H2AB O5A 0.842(14) 2.162(15) 3.003(4) 179(3) 2_576 N2A H2AC O5 0.842(14) 2.16(2) 2.929(4) 151(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 N1 C8 C9 O1 67.9(4) . . . . C1 C2 N1 C8 175.1(3) . . . . C2 C1 C7 O2 172.4(3) . . . . C2 C1 C7 O3 -7.0(5) . . . . C3 C2 N1 C8 -5.4(5) . . . . C4 C5 S1 O4 48.8(3) . . . . C4 C5 S1 O5 -80.2(3) . . . . C4 C5 S1 N2 165.4(3) . . . . C6 C1 C7 O2 -10.9(4) . . . . C6 C1 C7 O3 169.7(3) . . . . C6 C5 S1 O4 -130.4(3) . . . . C6 C5 S1 O5 100.6(3) . . . . C6 C5 S1 N2 -13.9(3) . . . . C9 C8 N1 C2 -83.7(4) . . . . C10 C9 C8 N1 -114.9(4) . . . . N1A C8A C9A O1A -57.3(4) . . . . C1A C2A N1A C8A 163.8(3) . . . . C2A C1A C7A O2A 179.1(3) . . . . C2A C1A C7A O3A -0.3(5) . . . . C3A C2A N1A C8A -16.9(5) . . . . C4A C5A S1A O4A 47.8(3) . . . . C4A C5A S1A O5A -81.4(3) . . . . C4A C5A S1A N2A 164.0(3) . . . . C6A C1A C7A O2A -4.7(4) . . . . C6A C1A C7A O3A 175.9(3) . . . . C6A C5A S1A O4A -130.5(3) . . . . C6A C5A S1A O5A 100.3(3) . . . . C6A C5A S1A N2A -14.3(3) . . . . C9A C8A N1A C2A -62.0(4) . . . . C10A C9A C8A N1A 121.2(4) . . . .