#------------------------------------------------------------------------------ #$Date: 2019-12-26 21:58:51 +0200 (Thu, 26 Dec 2019) $ #$Revision: 246129 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/31/18/2311834.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_2311834 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 +, C2 H5 O3 S -' _chemical_formula_moiety 'C10 H11 N4 O2 S +, C2 H5 O3 S -' _chemical_formula_sum 'C12 H16 N4 O5 S2' _chemical_formula_weight 360.41 _chemical_name_systematic ; 4-[(Pyrimidin-2-yl)sulfamoyl]anilinium ethanesulfonate ; _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 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 93.102(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.5269(4) _cell_length_b 34.979(3) _cell_length_c 8.4395(6) _cell_measurement_reflns_used 2991 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 28.6519 _cell_measurement_theta_min 3.3506 _cell_volume 1629.2(2) _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) and Mercury (Macrae et al., 2008) ; _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 0.991 _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 0.1038 _diffrn_reflns_av_sigmaI/netI 0.0985 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 19991 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 3.36 _exptl_absorpt_coefficient_mu 0.357 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90769 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Oxford Diffraction, 2010) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.354 _refine_diff_density_min -0.405 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 222 _refine_ls_number_reflns 3515 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.007 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0546 _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^)+(0.0391P)^2^+0.6311P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0947 _refine_ls_wR_factor_ref 0.1123 _reflns_number_gt 2212 _reflns_number_total 3515 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL brandon_sulfaetso3 in P 21/c CELL 0.71073 5.5269 34.9790 8.4395 90.000 93.102 90.000 ZERR 4.00 0.0004 0.0030 0.0006 0.000 0.007 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC S O N C H UNIT 8 20 16 48 64 MERG 2 OMIT -3.00 54.00 eqiv $1 x, -y+0.5, z+0.5 eqiv $2 x+1, y, z eqiv $3 x+1, -y+0.5, z+0.5 eqiv $4 -x+1, -y+1, -z+1 htab N1 O5_$1 htab N1 O4_$2 htab N1 O3_$3 htab N1 O5 htab N2 N4_$4 dfix 0.91 .01 n1 h1n n1 h2n n1 h3n FMAP 2 PLAN 20 ACTA 52.00 BOND $H CONF L.S. 4 TEMP -150.00 WGHT 0.039100 0.631100 FVAR 1.13332 S1 1 0.281922 0.440934 0.779102 11.00000 0.01936 0.01754 = 0.01670 -0.00066 0.00499 -0.00184 S2 1 0.009734 0.279302 0.232755 11.00000 0.01560 0.02132 = 0.01716 -0.00216 0.00029 -0.00033 O1 2 0.467629 0.454204 0.890178 11.00000 0.02680 0.02518 = 0.01522 -0.00290 0.00150 -0.00487 O2 2 0.037103 0.440022 0.824123 11.00000 0.02158 0.02229 = 0.02081 -0.00086 0.00844 0.00242 O3 2 -0.149755 0.246734 0.210357 11.00000 0.02036 0.02796 = 0.03539 0.00037 -0.00777 -0.00569 O4 2 -0.035631 0.301071 0.373878 11.00000 0.02381 0.03550 = 0.02201 -0.00999 0.00019 0.00422 O5 2 0.267049 0.268235 0.230149 11.00000 0.01394 0.02999 = 0.02277 -0.00521 0.00248 0.00317 N1 3 0.497205 0.286715 0.524078 11.00000 0.02155 0.01956 = 0.02301 -0.00392 -0.00361 0.00205 AFIX 2 H1N 5 0.452330 0.267096 0.585895 11.00000 -1.50000 H2N 5 0.655559 0.284110 0.505430 11.00000 -1.50000 H3N 5 0.419696 0.281834 0.427955 11.00000 -1.50000 AFIX 0 N2 3 0.308161 0.467873 0.622893 11.00000 0.01949 0.01837 = 0.01755 0.00197 0.00323 -0.00540 N3 3 0.001467 0.438043 0.466745 11.00000 0.02430 0.02289 = 0.02018 0.00011 0.00358 -0.00618 N4 3 0.279501 0.481585 0.356152 11.00000 0.02160 0.01685 = 0.01733 0.00165 0.00637 0.00112 C1 4 0.451180 0.324144 0.592971 11.00000 0.01510 0.01921 = 0.01497 -0.00290 -0.00506 0.00371 C2 4 0.244862 0.328917 0.675721 11.00000 0.01839 0.01601 = 0.02189 0.00186 -0.00271 -0.00183 AFIX 43 H2 5 0.138814 0.308072 0.691906 11.00000 -1.20000 AFIX 0 C3 4 0.196458 0.364870 0.734528 11.00000 0.01629 0.02038 = 0.01791 0.00276 0.00494 -0.00056 AFIX 43 H3 5 0.053793 0.369008 0.790082 11.00000 -1.20000 AFIX 0 C4 4 0.353702 0.394640 0.713004 11.00000 0.01641 0.01578 = 0.01407 0.00114 -0.00088 -0.00065 C5 4 0.565253 0.389239 0.633699 11.00000 0.01717 0.01968 = 0.01894 0.00122 0.00172 -0.00500 AFIX 43 H5 5 0.675047 0.409805 0.621749 11.00000 -1.20000 AFIX 0 C6 4 0.613431 0.353684 0.572734 11.00000 0.01352 0.02311 = 0.01855 -0.00286 0.00403 0.00028 AFIX 43 H6 5 0.756281 0.349477 0.517456 11.00000 -1.20000 AFIX 0 C7 4 0.189179 0.462048 0.475859 11.00000 0.01812 0.01560 = 0.01682 -0.00211 0.00555 0.00366 C8 4 -0.107012 0.434365 0.322272 11.00000 0.02509 0.02695 = 0.02613 -0.00486 0.00143 -0.00613 AFIX 43 H8 5 -0.243575 0.417920 0.310315 11.00000 -1.20000 AFIX 0 C9 4 -0.033061 0.452906 0.190184 11.00000 0.02804 0.02623 = 0.01536 -0.00015 0.00037 -0.00355 AFIX 43 H9 5 -0.113637 0.449729 0.088732 11.00000 -1.20000 AFIX 0 C10 4 0.166027 0.476498 0.213954 11.00000 0.03160 0.02033 = 0.01413 0.00090 0.00715 0.00429 AFIX 43 H10 5 0.224733 0.489667 0.125378 11.00000 -1.20000 AFIX 0 C11 4 -0.040217 0.309856 0.067580 11.00000 0.02659 0.03549 = 0.02642 0.00904 0.00451 -0.00253 AFIX 23 H11A 5 0.079252 0.330954 0.075161 11.00000 -1.20000 H11B 5 -0.012809 0.295326 -0.030507 11.00000 -1.20000 AFIX 0 C12 4 -0.294237 0.326740 0.055323 11.00000 0.03388 0.05356 = 0.04500 0.02050 -0.00194 0.00421 AFIX 137 H12A 5 -0.413560 0.306043 0.045038 11.00000 -1.50000 H12B 5 -0.311221 0.343398 -0.037982 11.00000 -1.50000 H12C 5 -0.321550 0.341655 0.151019 11.00000 -1.50000 AFIX 0 H4N 5 0.441983 0.482165 0.627483 11.00000 0.03124 HKLF 4 REM brandon_sulfaetso3 in P 21/c REM R1 = 0.0546 for 2212 Fo > 4sig(Fo) and 0.1104 for all 3515 data REM 222 parameters refined using 3 restraints END WGHT 0.0391 0.6374 REM Highest difference peak 0.354, deepest hole -0.405, 1-sigma level 0.081 Q1 1 0.3045 0.4174 0.6961 11.00000 0.05 0.35 Q2 1 -0.1786 0.4697 0.0355 11.00000 0.05 0.33 Q3 1 0.0375 0.3279 0.1670 11.00000 0.05 0.33 Q4 1 -0.0263 0.2925 0.1375 11.00000 0.05 0.32 Q5 1 0.1426 0.5213 0.0975 11.00000 0.05 0.31 Q6 1 0.2772 0.5004 0.2956 11.00000 0.05 0.31 Q7 1 0.0683 0.4166 0.8768 11.00000 0.05 0.30 Q8 1 -0.4891 0.4502 0.2739 11.00000 0.05 0.29 Q9 1 0.0799 0.4392 0.7628 11.00000 0.05 0.29 Q10 1 0.1628 0.4868 0.6392 11.00000 0.05 0.28 Q11 1 0.1961 0.4680 0.5748 11.00000 0.05 0.28 Q12 1 0.2969 0.4718 0.4165 11.00000 0.05 0.28 Q13 1 -0.1608 0.2305 0.0929 11.00000 0.05 0.27 Q14 1 0.4221 0.3979 0.6469 11.00000 0.05 0.27 Q15 1 0.5371 0.4381 0.5300 11.00000 0.05 0.26 Q16 1 0.7194 0.4493 0.9187 11.00000 0.05 0.26 Q17 1 0.4404 0.4909 0.3399 11.00000 0.05 0.26 Q18 1 -0.0418 0.2805 0.3364 11.00000 0.05 0.26 Q19 1 -0.0952 0.3506 0.1865 11.00000 0.05 0.25 Q20 1 0.3064 0.4546 0.6763 11.00000 0.05 0.25 ; _cod_data_source_file lg3144sup1.cif _cod_data_source_block VII _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2311834 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 S S1 0.28192(13) 0.44093(2) 0.77910(9) 0.0177(2) Uani d . 1 1 S S2 0.00973(13) 0.27930(2) 0.23275(9) 0.0181(2) Uani d . 1 1 O O1 0.4676(4) 0.45420(6) 0.8902(2) 0.0224(5) Uani d . 1 1 O O2 0.0371(4) 0.44002(6) 0.8241(2) 0.0213(5) Uani d . 1 1 O O3 -0.1498(4) 0.24673(6) 0.2104(3) 0.0282(6) Uani d . 1 1 O O4 -0.0356(4) 0.30107(7) 0.3739(3) 0.0271(6) Uani d . 1 1 O O5 0.2670(3) 0.26823(6) 0.2301(3) 0.0222(5) Uani d . 1 1 N N1 0.4972(5) 0.28671(8) 0.5241(3) 0.0215(6) Uani d D 1 1 H H1N 0.452(6) 0.2671(7) 0.586(3) 0.032 Uiso d D 1 1 H H2N 0.656(2) 0.2841(10) 0.505(4) 0.032 Uiso d D 1 1 H H3N 0.420(5) 0.2818(9) 0.428(2) 0.032 Uiso d D 1 1 N N2 0.3082(5) 0.46787(8) 0.6229(3) 0.0184(6) Uani d . 1 1 N N3 0.0015(5) 0.43804(8) 0.4667(3) 0.0224(6) Uani d . 1 1 N N4 0.2795(4) 0.48159(7) 0.3562(3) 0.0184(6) Uani d . 1 1 C C1 0.4512(5) 0.32414(9) 0.5930(4) 0.0166(7) Uani d . 1 1 C C2 0.2449(5) 0.32892(9) 0.6757(4) 0.0189(7) Uani d . 1 1 H H2 0.1388 0.3081 0.6919 0.023 Uiso calc R 1 1 C C3 0.1965(5) 0.36487(9) 0.7345(4) 0.0180(7) Uani d . 1 1 H H3 0.0538 0.3690 0.7901 0.022 Uiso calc R 1 1 C C4 0.3537(5) 0.39464(9) 0.7130(4) 0.0155(7) Uani d . 1 1 C C5 0.5653(5) 0.38924(9) 0.6337(4) 0.0186(7) Uani d . 1 1 H H5 0.6750 0.4098 0.6217 0.022 Uiso calc R 1 1 C C6 0.6134(5) 0.35368(9) 0.5727(4) 0.0183(7) Uani d . 1 1 H H6 0.7563 0.3495 0.5175 0.022 Uiso calc R 1 1 C C7 0.1892(5) 0.46205(9) 0.4759(4) 0.0167(7) Uani d . 1 1 C C8 -0.1070(6) 0.43437(10) 0.3223(4) 0.0261(8) Uani d . 1 1 H H8 -0.2436 0.4179 0.3103 0.031 Uiso calc R 1 1 C C9 -0.0331(6) 0.45291(9) 0.1902(4) 0.0232(8) Uani d . 1 1 H H9 -0.1136 0.4497 0.0887 0.028 Uiso calc R 1 1 C C10 0.1660(6) 0.47650(9) 0.2140(4) 0.0218(8) Uani d . 1 1 H H10 0.2247 0.4897 0.1254 0.026 Uiso calc R 1 1 C C11 -0.0402(6) 0.30986(10) 0.0676(4) 0.0294(9) Uani d . 1 1 H H11A 0.0793 0.3310 0.0752 0.035 Uiso calc R 1 1 H H11B -0.0128 0.2953 -0.0305 0.035 Uiso calc R 1 1 C C12 -0.2942(6) 0.32674(12) 0.0553(5) 0.0443(11) Uani d . 1 1 H H12A -0.4136 0.3060 0.0450 0.066 Uiso calc R 1 1 H H12B -0.3112 0.3434 -0.0380 0.066 Uiso calc R 1 1 H H12C -0.3215 0.3417 0.1510 0.066 Uiso calc R 1 1 H H4N 0.442(6) 0.4822(10) 0.627(4) 0.031(10) Uiso d . 1 1 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 S1 0.0194(4) 0.0175(4) 0.0167(4) -0.0018(3) 0.0050(3) -0.0007(4) S2 0.0156(4) 0.0213(5) 0.0172(4) -0.0003(3) 0.0003(3) -0.0022(4) O1 0.0268(12) 0.0252(13) 0.0152(12) -0.0049(10) 0.0015(9) -0.0029(10) O2 0.0216(11) 0.0223(13) 0.0208(13) 0.0024(10) 0.0084(9) -0.0009(10) O3 0.0204(12) 0.0280(14) 0.0354(15) -0.0057(10) -0.0078(10) 0.0004(12) O4 0.0238(12) 0.0355(15) 0.0220(13) 0.0042(11) 0.0002(10) -0.0100(11) O5 0.0139(11) 0.0300(14) 0.0228(13) 0.0032(10) 0.0025(9) -0.0052(10) N1 0.0216(15) 0.0196(16) 0.0230(17) 0.0020(13) -0.0036(13) -0.0039(13) N2 0.0195(14) 0.0184(16) 0.0176(15) -0.0054(13) 0.0032(12) 0.0020(12) N3 0.0243(15) 0.0229(16) 0.0202(16) -0.0062(13) 0.0036(12) 0.0001(13) N4 0.0216(14) 0.0168(15) 0.0173(15) 0.0011(11) 0.0064(11) 0.0017(12) C1 0.0151(16) 0.0192(18) 0.0150(17) 0.0037(13) -0.0051(13) -0.0029(14) C2 0.0184(17) 0.0160(18) 0.0219(18) -0.0018(14) -0.0027(14) 0.0019(15) C3 0.0163(16) 0.0204(18) 0.0179(18) -0.0006(14) 0.0049(13) 0.0028(15) C4 0.0164(16) 0.0158(17) 0.0141(17) -0.0006(13) -0.0009(13) 0.0011(14) C5 0.0172(16) 0.0197(18) 0.0189(18) -0.0050(14) 0.0017(13) 0.0012(15) C6 0.0135(16) 0.0231(19) 0.0186(18) 0.0003(14) 0.0040(13) -0.0029(15) C7 0.0181(16) 0.0156(18) 0.0168(18) 0.0037(13) 0.0055(13) -0.0021(14) C8 0.0251(18) 0.027(2) 0.026(2) -0.0061(15) 0.0014(15) -0.0049(16) C9 0.0280(18) 0.026(2) 0.0154(18) -0.0035(15) 0.0004(14) -0.0002(15) C10 0.0316(19) 0.0203(19) 0.0141(18) 0.0043(15) 0.0071(14) 0.0009(15) C11 0.0266(19) 0.035(2) 0.026(2) -0.0025(16) 0.0045(15) 0.0090(17) C12 0.034(2) 0.054(3) 0.045(3) 0.0042(19) -0.0019(19) 0.021(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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 O2 S1 O1 119.39(13) O2 S1 N2 110.80(13) O1 S1 N2 104.48(14) O2 S1 C4 107.25(14) O1 S1 C4 109.85(13) N2 S1 C4 104.06(14) O3 S2 O4 112.99(14) O3 S2 O5 111.87(13) O4 S2 O5 111.13(13) O3 S2 C11 107.77(15) O4 S2 C11 107.73(16) O5 S2 C11 104.87(14) C1 N1 H1N 113(2) C1 N1 H2N 111(2) H1N N1 H2N 109(3) C1 N1 H3N 116(2) H1N N1 H3N 104(3) H2N N1 H3N 104(3) C7 N2 S1 125.4(2) C7 N2 H4N 118(2) S1 N2 H4N 113(2) C7 N3 C8 115.0(3) C10 N4 C7 115.7(3) C2 C1 C6 122.1(3) C2 C1 N1 118.5(3) C6 C1 N1 119.5(3) C1 C2 C3 118.2(3) C1 C2 H2 120.9 C3 C2 H2 120.9 C4 C3 C2 120.4(3) C4 C3 H3 119.8 C2 C3 H3 119.8 C3 C4 C5 121.0(3) C3 C4 S1 119.9(2) C5 C4 S1 119.1(2) C6 C5 C4 119.1(3) C6 C5 H5 120.4 C4 C5 H5 120.4 C5 C6 C1 119.2(3) C5 C6 H6 120.4 C1 C6 H6 120.4 N3 C7 N4 126.8(3) N3 C7 N2 118.3(3) N4 C7 N2 115.0(3) N3 C8 C9 123.9(3) N3 C8 H8 118.0 C9 C8 H8 118.0 C8 C9 C10 115.8(3) C8 C9 H9 122.1 C10 C9 H9 122.1 N4 C10 C9 122.8(3) N4 C10 H10 118.6 C9 C10 H10 118.6 C12 C11 S2 113.1(2) C12 C11 H11A 109.0 S2 C11 H11A 109.0 C12 C11 H11B 109.0 S2 C11 H11B 109.0 H11A C11 H11B 107.8 C11 C12 H12A 109.5 C11 C12 H12B 109.5 H12A C12 H12B 109.5 C11 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O2 1.425(2) S1 O1 1.430(2) S1 N2 1.633(3) S1 C4 1.765(3) S2 O3 1.447(2) S2 O4 1.447(2) S2 O5 1.475(2) S2 C11 1.766(3) N1 C1 1.460(4) N1 H1N 0.905(10) N1 H2N 0.902(10) N1 H3N 0.913(10) N2 C7 1.388(4) N2 H4N 0.89(3) N3 C7 1.334(4) N3 C8 1.335(4) N4 C10 1.336(4) N4 C7 1.338(4) C1 C2 1.379(4) C1 C6 1.385(4) C2 C3 1.383(4) C2 H2 0.9500 C3 C4 1.375(4) C3 H3 0.9500 C4 C5 1.391(4) C5 C6 1.377(4) C5 H5 0.9500 C6 H6 0.9500 C8 C9 1.371(4) C8 H8 0.9500 C9 C10 1.381(4) C9 H9 0.9500 C10 H10 0.9500 C11 C12 1.521(5) C11 H11A 0.9900 C11 H11B 0.9900 C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 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 O5 4_566 0.905(10) 2.048(14) 2.929(4) 164(3) N1 H2N O4 1_655 0.902(10) 2.169(19) 2.980(4) 149(3) N1 H2N O3 4_666 0.902(10) 2.26(3) 2.705(3) 110(2) N1 H3N O5 . 0.913(10) 1.890(11) 2.801(3) 176(3) N2 H4N N4 3_666 0.89(3) 1.99(3) 2.882(4) 174(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 O2 S1 N2 C7 -60.0(3) O1 S1 N2 C7 170.2(2) C4 S1 N2 C7 55.0(3) C6 C1 C2 C3 2.4(4) N1 C1 C2 C3 -177.1(3) C1 C2 C3 C4 -1.3(4) C2 C3 C4 C5 -0.8(5) C2 C3 C4 S1 176.6(2) O2 S1 C4 C3 -9.6(3) O1 S1 C4 C3 121.6(2) N2 S1 C4 C3 -127.1(3) O2 S1 C4 C5 167.8(2) O1 S1 C4 C5 -61.1(3) N2 S1 C4 C5 50.3(3) C3 C4 C5 C6 1.7(5) S1 C4 C5 C6 -175.7(2) C4 C5 C6 C1 -0.5(4) C2 C1 C6 C5 -1.6(5) N1 C1 C6 C5 178.0(3) C8 N3 C7 N4 -1.6(5) C8 N3 C7 N2 178.8(3) C10 N4 C7 N3 0.8(4) C10 N4 C7 N2 -179.6(3) S1 N2 C7 N3 15.1(4) S1 N2 C7 N4 -164.5(2) C7 N3 C8 C9 1.1(5) N3 C8 C9 C10 -0.1(5) C7 N4 C10 C9 0.5(4) C8 C9 C10 N4 -0.8(5) O3 S2 C11 C12 64.5(3) O4 S2 C11 C12 -57.7(3) O5 S2 C11 C12 -176.1(3)