#------------------------------------------------------------------------------ #$Date: 2019-12-26 21:58:51 +0200 (Thu, 26 Dec 2019) $ #$Revision: 246129 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/31/18/2311830.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2311830 loop_ _publ_author_name 'Buist, Amanda R.' 'Dennany, Lynn' 'Kennedy, Alan R.' 'Manzie, Craig' 'McPhie, Katherine' 'Walker, Brandon' _publ_section_title ; Eight salt forms of sulfadiazine. ; _journal_coeditor_code LG3144 _journal_issue 'Pt 9' _journal_name_full 'Acta crystallographica. Section C, Structural chemistry' _journal_page_first 900 _journal_page_last 907 _journal_paper_doi 10.1107/S2053229614018725 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac 'C10 H11 N4 O2 S +, Br -, H2 O' _chemical_formula_moiety 'C10 H11 N4 O2 S +, Br -, H2 O' _chemical_formula_sum 'C10 H13 Br N4 O3 S' _chemical_formula_weight 349.21 _chemical_name_systematic ; 2-{[(4-Azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium bromide monohydrate ; _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 98.380(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.9420(3) _cell_length_b 5.6295(2) _cell_length_c 21.0659(6) _cell_measurement_reflns_used 4492 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 29.8208 _cell_measurement_theta_min 3.1714 _cell_volume 1401.09(7) _computing_cell_refinement 'CrysAlis PRO (Oxford Diffraction, 2010)' _computing_data_collection 'CrysAlis PRO (Oxford Diffraction, 2010)' _computing_data_reduction 'CrysAlis PRO (Oxford Diffraction, 2010)' _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 2012) ; _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 123(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur E' _diffrn_measurement_method 'omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 8186 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 3.71 _exptl_absorpt_coefficient_mu 3.092 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.61596 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Oxford Diffraction, 2010) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.456 _refine_diff_density_min -0.521 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 3353 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0289 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0308P)^2^+0.9997P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.0723 _reflns_number_gt 2868 _reflns_number_total 3353 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL craigsulfbr in P 21/n CELL 0.71073 11.9420 5.6295 21.0659 90.000 98.380 90.000 ZERR 4.00 0.0003 0.0002 0.0006 0.000 0.003 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC BR S O N C H UNIT 4 4 12 16 40 52 MERG 2 OMIT -3.00 56.00 shel .5 5.6 DFIX .88 .01 O1W H1W O1W H2W N3 H4N DFIX 1.33 .02 H1W H2W eadp o1w o2w o3w o4w sump 1 .001 1 2 1 3 1 4 1 5 eqiv $1 1-x, 2-y, 2-z htab n1 br1 htab n1 o2_$1 eqiv $2 -x+0.5, y+0.5, -z+3/2 htab n1 br1_$2 eqiv $3 x, y+1, z htab n1 Br1_$3 eqiv $4 -x+2, -y+2, -z+2 htab n3 n2_$4 htab n3 o2_$4 FMAP 2 PLAN 20 ACTA 54.00 BOND $H CONF L.S. 8 TEMP -150.00 WGHT 0.030800 0.999700 FVAR 4.16762 0.45277 0.24808 0.16119 0.13914 BR1 1 0.401273 0.499394 0.747817 11.00000 0.01972 0.01516 = 0.01408 0.00103 0.00096 -0.00096 S1 2 0.763259 0.824812 1.032113 11.00000 0.00886 0.01511 = 0.01196 0.00101 0.00132 -0.00232 O1 3 0.745250 0.593091 1.057680 11.00000 0.01348 0.01924 = 0.02132 0.00807 -0.00041 -0.00330 O2 3 0.768001 1.020524 1.077031 11.00000 0.01276 0.02252 = 0.01377 -0.00463 0.00329 -0.00270 N1 4 0.371464 0.998399 0.826548 11.00000 0.01122 0.01622 = 0.01308 0.00213 -0.00005 -0.00126 AFIX 2 H1N 6 0.359880 0.869649 0.800413 11.00000 -1.50000 H2N 6 0.309555 1.005891 0.844743 11.00000 -1.50000 H3N 6 0.377791 1.126960 0.805812 11.00000 -1.50000 AFIX 0 N2 4 0.877835 0.852992 1.001553 11.00000 0.00929 0.01497 = 0.01538 -0.00166 0.00329 -0.00252 N3 4 0.999721 0.755478 0.932440 11.00000 0.01054 0.01358 = 0.01448 -0.00084 0.00166 -0.00181 AFIX 2 H4N 6 1.037439 0.871487 0.952658 11.00000 -1.20000 AFIX 0 N4 4 0.833615 0.529745 0.929313 11.00000 0.01558 0.01799 = 0.02082 -0.00355 0.00328 -0.00573 C4 5 0.649218 0.880893 0.970234 11.00000 0.00975 0.01415 = 0.01167 0.00010 0.00213 0.00004 C3 5 0.567496 0.706766 0.956215 11.00000 0.01355 0.01159 = 0.01410 0.00346 0.00175 -0.00179 AFIX 43 H3 6 0.574621 0.559630 0.978522 11.00000 -1.20000 AFIX 0 C2 5 0.474702 0.748334 0.909213 11.00000 0.01160 0.01275 = 0.01703 -0.00055 0.00242 -0.00434 AFIX 43 H2 6 0.416404 0.633195 0.900154 11.00000 -1.20000 AFIX 0 C1 5 0.469494 0.960252 0.876203 11.00000 0.00929 0.01616 = 0.00935 -0.00043 0.00137 0.00048 C6 5 0.551685 1.134626 0.889069 11.00000 0.01682 0.01182 = 0.01495 0.00177 0.00195 -0.00164 AFIX 43 H6 6 0.546386 1.278315 0.865169 11.00000 -1.20000 AFIX 0 C5 5 0.641976 1.095559 0.937542 11.00000 0.01401 0.01292 = 0.01851 0.00097 0.00076 -0.00517 AFIX 43 H5 6 0.698045 1.214434 0.948152 11.00000 -1.20000 AFIX 0 C7 5 0.900444 0.708341 0.954725 11.00000 0.01153 0.01190 = 0.01505 0.00294 0.00110 -0.00015 C10 5 0.869419 0.404692 0.882062 11.00000 0.02094 0.02047 = 0.02352 -0.00605 0.00269 -0.00617 AFIX 43 H10 6 0.822901 0.278045 0.863809 11.00000 -1.20000 AFIX 0 C9 5 0.969314 0.446717 0.857917 11.00000 0.02190 0.01972 = 0.01943 -0.00699 0.00524 0.00070 AFIX 43 H9 6 0.991203 0.353200 0.824251 11.00000 -1.20000 AFIX 0 C8 5 1.035133 0.630289 0.885067 11.00000 0.01266 0.01880 = 0.01549 0.00209 0.00301 0.00250 AFIX 43 H8 6 1.104656 0.668000 0.870518 11.00000 -1.20000 AFIX 0 PART 1 O1W 3 0.802577 0.023949 0.762639 21.00000 0.02580 0.03733 = 0.05267 -0.01785 0.00574 -0.00313 AFIX 2 H1W 6 0.826088 -0.122210 0.759127 21.00000 -1.50000 H2W 6 0.829885 0.088387 0.730242 21.00000 -1.50000 AFIX 0 PART 2 O2W 3 0.809365 -0.081538 0.767507 31.00000 0.02580 0.03733 = 0.05267 -0.01785 0.00574 -0.00313 O3W 3 0.813069 0.140557 0.732088 41.00000 0.02580 0.03733 = 0.05267 -0.01785 0.00574 -0.00313 O4W 3 0.777964 0.299982 0.701928 51.00000 0.02580 0.03733 = 0.05267 -0.01785 0.00574 -0.00313 HKLF 4 REM craigsulfbr in P 21/n REM R1 = 0.0289 for 2868 Fo > 4sig(Fo) and 0.0378 for all 3353 data REM 203 parameters refined using 5 restraints END WGHT 0.0308 0.9991 REM Highest difference peak 0.456, deepest hole -0.521, 1-sigma level 0.086 Q1 1 0.8780 -0.0133 0.7568 11.00000 0.05 0.46 Q2 1 0.7038 0.8145 0.9914 11.00000 0.05 0.43 Q3 1 0.5287 0.7210 0.9263 11.00000 0.05 0.37 Q4 1 0.8017 -0.1847 0.7528 11.00000 0.05 0.35 Q5 1 0.8259 0.8417 1.0106 11.00000 0.05 0.34 Q6 1 0.8014 0.1301 0.7560 11.00000 0.05 0.33 Q7 1 0.7605 0.3650 0.7054 11.00000 0.05 0.32 Q8 1 1.0157 0.4953 0.8798 11.00000 0.05 0.32 Q9 1 1.0142 0.6677 0.9166 11.00000 0.05 0.31 Q10 1 0.5989 1.0970 0.9123 11.00000 0.05 0.31 Q11 1 0.4690 0.8628 0.9009 11.00000 0.05 0.31 Q12 1 0.8194 -0.0544 0.7954 11.00000 0.05 0.30 Q13 1 0.6003 0.8102 0.9723 11.00000 0.05 0.30 Q14 1 0.4363 0.9760 0.8590 11.00000 0.05 0.28 Q15 1 0.8761 0.8215 0.9697 11.00000 0.05 0.27 Q16 1 0.6479 0.9757 0.9599 11.00000 0.05 0.27 Q17 1 0.4567 0.6444 0.7622 11.00000 0.05 0.26 Q18 1 0.9408 0.7747 0.9267 11.00000 0.05 0.26 Q19 1 0.2390 0.7373 0.7692 11.00000 0.05 0.26 Q20 1 0.8590 0.4891 1.0300 11.00000 0.05 0.26 ; _cod_data_source_file lg3144sup1.cif _cod_data_source_block III _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2311830 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group Br Br1 0.401273(18) 0.49939(4) 0.747817(10) 0.01647(8) Uani d . 1 1 . . S S1 0.76326(4) 0.82481(10) 1.03211(2) 0.01199(12) Uani d . 1 1 . . O O1 0.74525(12) 0.5931(3) 1.05768(8) 0.0183(3) Uani d . 1 1 . . O O2 0.76800(13) 1.0205(3) 1.07703(8) 0.0162(3) Uani d . 1 1 . . N N1 0.37146(16) 0.9984(4) 0.82655(9) 0.0137(4) Uani d . 1 1 . . H H1N 0.360(2) 0.870(5) 0.8004(13) 0.021 Uiso d . 1 1 . . H H2N 0.310(3) 1.006(4) 0.8447(14) 0.021 Uiso d . 1 1 . . H H3N 0.378(2) 1.127(5) 0.8058(13) 0.021 Uiso d . 1 1 . . N N2 0.87783(14) 0.8530(3) 1.00155(9) 0.0131(4) Uani d . 1 1 . . N N3 0.99972(14) 0.7555(3) 0.93244(9) 0.0129(4) Uani d D 1 1 . . H H4N 1.0374(18) 0.871(3) 0.9527(11) 0.015 Uiso d D 1 1 . . N N4 0.83362(16) 0.5297(3) 0.92931(10) 0.0181(4) Uani d . 1 1 . . C C4 0.64922(16) 0.8809(4) 0.97023(10) 0.0118(4) Uani d . 1 1 . . C C3 0.56750(17) 0.7068(4) 0.95621(10) 0.0131(4) Uani d . 1 1 . . H H3 0.5746 0.5596 0.9785 0.016 Uiso calc R 1 1 . . C C2 0.47470(17) 0.7483(4) 0.90921(10) 0.0138(4) Uani d . 1 1 . . H H2 0.4164 0.6332 0.9002 0.017 Uiso calc R 1 1 . . C C1 0.46949(17) 0.9603(4) 0.87620(10) 0.0116(4) Uani d . 1 1 . . C C6 0.55169(17) 1.1346(4) 0.88907(10) 0.0146(4) Uani d . 1 1 . . H H6 0.5464 1.2783 0.8652 0.017 Uiso calc R 1 1 . . C C5 0.64198(18) 1.0956(4) 0.93754(11) 0.0153(4) Uani d . 1 1 . . H H5 0.6980 1.2144 0.9482 0.018 Uiso calc R 1 1 . . C C7 0.90044(17) 0.7083(4) 0.95472(10) 0.0129(4) Uani d . 1 1 . . C C10 0.86942(19) 0.4047(5) 0.88206(12) 0.0217(5) Uani d . 1 1 . . H H10 0.8229 0.2780 0.8638 0.026 Uiso calc R 1 1 . . C C9 0.9693(2) 0.4467(4) 0.85792(12) 0.0201(5) Uani d . 1 1 . . H H9 0.9912 0.3532 0.8243 0.024 Uiso calc R 1 1 . . C C8 1.03513(18) 0.6303(4) 0.88507(10) 0.0156(5) Uani d . 1 1 . . H H8 1.1047 0.6680 0.8705 0.019 Uiso calc R 1 1 . . O O1W 0.8026(5) 0.0239(18) 0.7626(4) 0.0386(16) Uani d PD 0.453(10) 1 A 1 H H1W 0.826(8) -0.122(6) 0.759(5) 0.058 Uiso d PD 0.45 1 A 1 H H2W 0.830(9) 0.088(16) 0.730(4) 0.058 Uiso d PD 0.45 1 A 1 O O2W 0.8094(12) -0.082(3) 0.7675(8) 0.0386(16) Uani d P 0.248(10) 1 . 2 O O3W 0.8131(13) 0.141(3) 0.7321(9) 0.0386(16) Uani d P 0.161(6) 1 B 2 O O4W 0.7780(11) 0.300(3) 0.7019(8) 0.0386(16) Uani d P 0.139(4) 1 . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.01972(12) 0.01516(13) 0.01408(12) -0.00096(8) 0.00096(8) 0.00103(8) S1 0.0089(2) 0.0151(3) 0.0120(2) -0.0023(2) 0.00132(17) 0.0010(2) O1 0.0135(7) 0.0192(8) 0.0213(9) -0.0033(6) -0.0004(6) 0.0081(7) O2 0.0128(7) 0.0225(9) 0.0138(8) -0.0027(6) 0.0033(6) -0.0046(6) N1 0.0112(8) 0.0162(10) 0.0131(9) -0.0013(7) 0.0000(7) 0.0021(8) N2 0.0093(8) 0.0150(10) 0.0154(9) -0.0025(7) 0.0033(6) -0.0017(7) N3 0.0105(8) 0.0136(9) 0.0145(9) -0.0018(7) 0.0017(6) -0.0008(7) N4 0.0156(9) 0.0180(11) 0.0208(10) -0.0057(7) 0.0033(7) -0.0036(8) C4 0.0098(9) 0.0141(11) 0.0117(10) 0.0000(8) 0.0021(7) 0.0001(8) C3 0.0135(10) 0.0116(11) 0.0141(10) -0.0018(8) 0.0017(8) 0.0035(8) C2 0.0116(9) 0.0127(11) 0.0170(11) -0.0043(8) 0.0024(8) -0.0005(8) C1 0.0093(9) 0.0162(11) 0.0094(10) 0.0005(8) 0.0014(7) -0.0004(8) C6 0.0168(10) 0.0118(11) 0.0149(11) -0.0016(8) 0.0019(8) 0.0018(8) C5 0.0140(10) 0.0129(11) 0.0185(11) -0.0052(8) 0.0008(8) 0.0010(9) C7 0.0115(9) 0.0119(11) 0.0151(11) -0.0001(8) 0.0011(7) 0.0029(8) C10 0.0209(11) 0.0205(12) 0.0235(13) -0.0062(10) 0.0027(9) -0.0061(10) C9 0.0219(11) 0.0197(13) 0.0194(12) 0.0007(9) 0.0052(9) -0.0070(9) C8 0.0127(10) 0.0188(12) 0.0155(11) 0.0025(8) 0.0030(8) 0.0021(9) O1W 0.0258(17) 0.037(5) 0.053(3) -0.003(3) 0.0057(17) -0.018(3) O2W 0.0258(17) 0.037(5) 0.053(3) -0.003(3) 0.0057(17) -0.018(3) O3W 0.0258(17) 0.037(5) 0.053(3) -0.003(3) 0.0057(17) -0.018(3) O4W 0.0258(17) 0.037(5) 0.053(3) -0.003(3) 0.0057(17) -0.018(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Br Br -0.2901 2.4595 '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' O O 0.0106 0.0060 '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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 S1 O2 116.03(10) O1 S1 N2 115.02(10) O2 S1 N2 103.46(9) O1 S1 C4 107.23(10) O2 S1 C4 107.34(10) N2 S1 C4 107.26(10) C1 N1 H1N 110.5(16) C1 N1 H2N 109.2(19) H1N N1 H2N 104(2) C1 N1 H3N 111.6(18) H1N N1 H3N 113(3) H2N N1 H3N 109(2) C7 N2 S1 120.81(15) C8 N3 C7 122.61(19) C8 N3 H4N 124.3(17) C7 N3 H4N 113.1(17) C10 N4 C7 117.0(2) C3 C4 C5 121.32(18) C3 C4 S1 118.25(16) C5 C4 S1 120.42(15) C4 C3 C2 119.7(2) C4 C3 H3 120.2 C2 C3 H3 120.2 C1 C2 C3 118.46(19) C1 C2 H2 120.8 C3 C2 H2 120.8 C2 C1 C6 122.39(19) C2 C1 N1 117.33(18) C6 C1 N1 120.27(19) C1 C6 C5 118.9(2) C1 C6 H6 120.6 C5 C6 H6 120.6 C4 C5 C6 119.2(2) C4 C5 H5 120.4 C6 C5 H5 120.4 N2 C7 N4 125.2(2) N2 C7 N3 114.51(18) N4 C7 N3 120.2(2) N4 C10 C9 124.7(2) N4 C10 H10 117.7 C9 C10 H10 117.7 C8 C9 C10 116.6(2) C8 C9 H9 121.7 C10 C9 H9 121.7 N3 C8 C9 118.9(2) N3 C8 H8 120.6 C9 C8 H8 120.6 H1W O1W H2W 99(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance S1 O1 . 1.4394(17) S1 O2 . 1.4480(16) S1 N2 . 1.6026(18) S1 C4 . 1.771(2) N1 C1 . 1.468(3) N1 H1N . 0.91(3) N1 H2N . 0.88(3) N1 H3N . 0.85(3) N2 C7 . 1.337(3) N3 C8 . 1.340(3) N3 C7 . 1.363(3) N3 H4N . 0.869(10) N4 C10 . 1.339(3) N4 C7 . 1.345(3) C4 C3 . 1.384(3) C4 C5 . 1.387(3) C3 C2 . 1.394(3) C3 H3 . 0.9500 C2 C1 . 1.378(3) C2 H2 . 0.9500 C1 C6 . 1.387(3) C6 C5 . 1.390(3) C6 H6 . 0.9500 C5 H5 . 0.9500 C10 C9 . 1.384(3) C10 H10 . 0.9500 C9 C8 . 1.372(3) C9 H9 . 0.9500 C8 H8 . 0.9500 O1W H1W . 0.876(10) O1W H2W . 0.877(10) O2W O3W . 1.46(2) O2W O4W 2_646 1.46(2) O3W O4W . 1.14(2) O4W O2W 2_656 1.46(2) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1N Br1 . 0.91(3) 2.44(3) 3.308(2) 159(2) N1 H2N O2 3_677 0.88(3) 2.01(3) 2.810(3) 150(3) N1 H2N Br1 2_556 0.88(3) 2.95(3) 3.4022(18) 114(2) N1 H3N Br1 1_565 0.85(3) 2.46(3) 3.317(2) 178(2) N3 H4N N2 3_777 0.869(10) 2.019(10) 2.887(2) 179(2) N3 H4N O2 3_777 0.869(10) 2.57(2) 3.080(2) 119(2) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion O1 S1 N2 C7 55.99(19) O2 S1 N2 C7 -176.45(16) C4 S1 N2 C7 -63.17(19) O1 S1 C4 C3 -0.9(2) O2 S1 C4 C3 -126.17(18) N2 S1 C4 C3 123.19(18) O1 S1 C4 C5 178.30(18) O2 S1 C4 C5 53.0(2) N2 S1 C4 C5 -57.6(2) C5 C4 C3 C2 -1.2(3) S1 C4 C3 C2 177.92(17) C4 C3 C2 C1 2.4(3) C3 C2 C1 C6 -1.5(3) C3 C2 C1 N1 179.4(2) C2 C1 C6 C5 -0.8(3) N1 C1 C6 C5 178.3(2) C3 C4 C5 C6 -1.0(3) S1 C4 C5 C6 179.84(18) C1 C6 C5 C4 2.0(3) S1 N2 C7 N4 -0.6(3) S1 N2 C7 N3 178.80(14) C10 N4 C7 N2 179.2(2) C10 N4 C7 N3 -0.1(3) C8 N3 C7 N2 -179.16(19) C8 N3 C7 N4 0.2(3) C7 N4 C10 C9 -0.1(4) N4 C10 C9 C8 0.1(4) C7 N3 C8 C9 -0.2(3) C10 C9 C8 N3 0.1(3)