#------------------------------------------------------------------------------ #$Date: 2014-10-25 20:23:10 +0300 (Sat, 25 Oct 2014) $ #$Revision: 125873 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/83/2018301.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_2018301 loop_ _publ_author_name 'Tutughamiarso, Maya' 'Bolte, Michael' _publ_section_title ; A new polymorph and two pseudopolymorphs of pyrimethamine ; _journal_coeditor_code SK3416 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o428 _journal_page_last o434 _journal_volume 67 _journal_year 2011 _chemical_formula_iupac 'C12 H13 Cl N4 , C2 H6 O S' _chemical_formula_moiety 'C12 H13 Cl N4, C2 H6 O S' _chemical_formula_sum 'C14 H19 Cl N4 O S' _chemical_formula_weight 326.84 _chemical_name_systematic ; 2,4-diamino-5(4-chlorophenyl)-6-ethylpyrimidine dimethyl sulfoxide monosolvate ; _space_group_IT_number 14 _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 SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 111.609(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.5596(9) _cell_length_b 7.7212(4) _cell_length_c 16.2870(11) _cell_measurement_reflns_used 7272 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.99 _cell_measurement_theta_min 3.65 _cell_volume 1585.35(18) _computing_cell_refinement 'X-AREA (Stoe & Cie, 2001)' _computing_data_collection 'X-AREA (Stoe & Cie, 2001)' _computing_data_reduction 'X-AREA (Stoe & Cie, 2001)' _computing_molecular_graphics ; Mercury (Version 2.2; Macrae et al., 2008) and XP (Sheldrick, 2008) ; _computing_publication_material 'publCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_device_type 'Stoe IPDS II two-circle' _diffrn_measurement_method \w _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 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 7296 _diffrn_reflns_theta_full 25.68 _diffrn_reflns_theta_max 25.68 _diffrn_reflns_theta_min 3.60 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.377 _exptl_absorpt_correction_T_max 0.8953 _exptl_absorpt_correction_T_min 0.8339 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '[MULABS (Spek, 2009; Blessing, 1995)]' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 688 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.299 _refine_diff_density_min -0.248 _refine_ls_extinction_coef 0.020(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)' _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 2939 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.002 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0409 _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^)+(0.0627P)^2^+0.6444P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1048 _refine_ls_wR_factor_ref 0.1096 _reflns_number_gt 2615 _reflns_number_total 2939 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL Ia in P2(1)/n CELL 0.71073 13.5596 7.7212 16.2870 90.000 111.609 90.000 ZERR 4.00 0.0009 0.0004 0.0011 0.000 0.005 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H CL N O S UNIT 56 76 4 16 4 4 SIZE 0.3 0.4 0.5 REM farbloser Block ACTA L.S. 10 BOND $H CONF FMAP 2 PLAN 10 TEMP -100 HFIX 23 -1.2 C61 HFIX 33 -1.5 C62 HFIX 43 -1.2 C52 C53 C55 C56 EQIV_$1 x-1/2, -y+3/2, z-1/2 EQIV_$2 -x+1, -y+2, -z+1 HTAB N21 Cl1_$1 HTAB N21 O1X_$2 HTAB N41 N3_$2 HTAB N41 O1X WGHT 0.0627 0.6444 EXTI 0.034854 FVAR 0.71787 0.55958 N1 4 0.59303 0.96817 0.27414 11.00000 0.02477 0.02170 = 0.02292 0.00047 0.01149 0.00223 C2 1 0.54371 1.04877 0.32024 11.00000 0.02376 0.01785 = 0.02067 -0.00042 0.00824 -0.00081 N3 4 0.54583 1.00764 0.40149 11.00000 0.02610 0.01955 = 0.02262 0.00042 0.01176 0.00379 C4 1 0.60886 0.87192 0.44116 11.00000 0.02624 0.01953 = 0.01961 -0.00142 0.01082 -0.00020 C5 1 0.66697 0.77973 0.39963 11.00000 0.02170 0.01795 = 0.02141 -0.00244 0.00979 -0.00004 C6 1 0.65535 0.83170 0.31483 11.00000 0.01930 0.02085 = 0.02144 -0.00204 0.01155 -0.00170 N21 4 0.48314 1.18848 0.28057 11.00000 0.04067 0.03141 = 0.02299 0.00607 0.01607 0.01302 H211 2 0.47626 1.20697 0.22953 11.00000 0.03088 H212 2 0.44714 1.23541 0.30900 11.00000 0.04629 N41 4 0.61009 0.82926 0.52179 11.00000 0.04155 0.02731 = 0.02451 0.00501 0.02171 0.01410 H411 2 0.56674 0.87861 0.54338 11.00000 0.02705 H412 2 0.63905 0.72933 0.54613 11.00000 0.04328 C51 1 0.73485 0.62856 0.44368 11.00000 0.02578 0.02114 = 0.01913 -0.00013 0.01459 0.00343 C52 1 0.83476 0.65186 0.50922 11.00000 0.02772 0.02083 = 0.02743 -0.00496 0.01000 -0.00043 C53 1 0.90047 0.51261 0.54716 11.00000 0.02846 0.02824 = 0.02574 -0.00179 0.00392 0.00229 C54 1 0.86452 0.34735 0.51809 11.00000 0.03135 0.02398 = 0.02016 0.00351 0.01717 0.00785 C55 1 0.76599 0.31880 0.45444 11.00000 0.03316 0.02086 = 0.02454 -0.00286 0.01334 -0.00145 C56 1 0.70092 0.46009 0.41825 11.00000 0.02574 0.02359 = 0.02293 -0.00128 0.00696 -0.00163 C61 1 0.70624 0.73913 0.25993 11.00000 0.02627 0.02540 = 0.02283 -0.00071 0.01791 0.00140 C62 1 0.62650 0.62290 0.19112 11.00000 0.03484 0.02808 = 0.02284 -0.00388 0.01231 0.00121 CL1 3 0.94668 0.17022 0.56355 11.00000 0.04360 0.02847 = 0.03011 0.00524 0.01233 0.01469 O1X 5 0.65512 0.57849 0.66530 11.00000 0.06702 0.02580 = 0.05244 0.01331 0.03376 0.01133 PART 1 S2X 6 0.60177 0.40850 0.66238 21.00000 0.02655 0.03327 = 0.03158 0.00008 0.01222 0.00239 PART 2 S2X' 6 0.70367 0.41739 0.70978 -21.00000 0.03059 0.02366 = 0.03819 0.00121 0.02004 0.00160 PART 0 C3X 1 0.63184 0.33870 0.77067 11.00000 0.05967 0.03766 = 0.04040 0.00447 0.03465 -0.00060 AFIX 33 PART 1 H3XA 2 0.59637 0.41365 0.79981 21.00000 -1.50000 H3XB 2 0.70872 0.34389 0.80279 21.00000 -1.50000 H3XC 2 0.60736 0.21928 0.77032 21.00000 -1.50000 PART 2 H3XD 2 0.63978 0.41751 0.81987 -21.00000 -1.50000 H3XE 2 0.65845 0.22384 0.79391 -21.00000 -1.50000 H3XF 2 0.55675 0.33031 0.73259 -21.00000 -1.50000 AFIX 0 PART 0 C4X 1 0.67520 0.25226 0.62856 11.00000 0.05374 0.03431 = 0.04563 -0.00880 0.03184 -0.00053 AFIX 33 PART 1 H4XA 2 0.66645 0.27353 0.56691 21.00000 -1.50000 H4XB 2 0.64920 0.13610 0.63394 21.00000 -1.50000 H4XC 2 0.75045 0.26098 0.66618 21.00000 -1.50000 PART 2 H4XD 2 0.71102 0.27828 0.58759 -21.00000 -1.50000 H4XE 2 0.59846 0.24650 0.59585 -21.00000 -1.50000 H4XF 2 0.70040 0.14081 0.65739 -21.00000 -1.50000 AFIX 0 PART 0 HKLF 4 END ; _[local]_cod_data_source_file sk3416.cif _[local]_cod_data_source_block Ia _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_original_cell_volume 1585.35(17) _cod_database_code 2018301 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 N N1 0.59331(12) 0.96779(19) 0.27418(9) 0.0220(3) Uani d . 1 1 . . C C2 0.54315(14) 1.0490(2) 0.32031(11) 0.0208(4) Uani d . 1 1 . . N N3 0.54644(12) 1.00771(19) 0.40151(9) 0.0221(3) Uani d . 1 1 . . C C4 0.60824(14) 0.8725(2) 0.44101(11) 0.0213(4) Uani d . 1 1 . . C C5 0.66741(14) 0.7791(2) 0.39949(10) 0.0200(4) Uani d . 1 1 . . C C6 0.65485(14) 0.8323(2) 0.31493(11) 0.0200(4) Uani d . 1 1 . . N N21 0.48311(15) 1.1879(2) 0.28079(11) 0.0308(4) Uani d . 1 1 . . H H211 0.4759(19) 1.208(3) 0.2277(16) 0.032(6) Uiso d . 1 1 . . H H212 0.446(2) 1.241(4) 0.3051(17) 0.043(7) Uiso d . 1 1 . . N N41 0.61030(15) 0.8293(2) 0.52169(10) 0.0293(4) Uani d . 1 1 . . H H411 0.567(2) 0.879(3) 0.5396(16) 0.035(6) Uiso d . 1 1 . . H H412 0.640(2) 0.732(4) 0.5461(16) 0.037(6) Uiso d . 1 1 . . C C51 0.73493(14) 0.6282(2) 0.44354(10) 0.0207(4) Uani d . 1 1 . . C C52 0.83494(15) 0.6519(2) 0.50927(12) 0.0263(4) Uani d . 1 1 . . H H52 0.8587 0.7660 0.5284 0.032 Uiso calc R 1 1 . . C C53 0.90030(15) 0.5126(3) 0.54714(12) 0.0281(4) Uani d . 1 1 . . H H53 0.9681 0.5300 0.5920 0.034 Uiso calc R 1 1 . . C C54 0.86460(15) 0.3478(2) 0.51821(11) 0.0240(4) Uani d . 1 1 . . C C55 0.76576(16) 0.3188(2) 0.45428(12) 0.0254(4) Uani d . 1 1 . . H H55 0.7425 0.2045 0.4353 0.030 Uiso calc R 1 1 . . C C56 0.70096(15) 0.4602(2) 0.41813(11) 0.0240(4) Uani d . 1 1 . . H H56 0.6320 0.4414 0.3752 0.029 Uiso calc R 1 1 . . C C61 0.70662(14) 0.7389(2) 0.25973(11) 0.0237(4) Uani d . 1 1 . . H H61A 0.7662 0.6675 0.2986 0.028 Uiso calc R 1 1 . . H H61B 0.7356 0.8247 0.2294 0.028 Uiso calc R 1 1 . . C C62 0.62655(16) 0.6230(3) 0.19121(11) 0.0280(4) Uani d . 1 1 . . H H62A 0.6615 0.5638 0.1561 0.042 Uiso calc R 1 1 . . H H62B 0.5681 0.6939 0.1523 0.042 Uiso calc R 1 1 . . H H62C 0.5987 0.5369 0.2213 0.042 Uiso calc R 1 1 . . Cl Cl1 0.94680(4) 0.17022(6) 0.56355(3) 0.03477(18) Uani d . 1 1 . . O O1X 0.65500(15) 0.5785(2) 0.66513(11) 0.0447(4) Uani d . 1 1 . . S S2X 0.60153(7) 0.40852(12) 0.66242(6) 0.0311(3) Uani d P 0.564(2) 1 A 1 S S2X' 0.70407(9) 0.41757(14) 0.70965(7) 0.0291(4) Uani d P 0.436(2) 1 A 2 C C3X 0.6318(2) 0.3388(3) 0.77096(15) 0.0428(5) Uani d . 1 1 . . H H3XA 0.5963 0.4139 0.8001 0.064 Uiso calc PR 0.564(2) 1 A 1 H H3XB 0.7087 0.3442 0.8030 0.064 Uiso calc PR 0.564(2) 1 A 1 H H3XC 0.6074 0.2193 0.7707 0.064 Uiso calc PR 0.564(2) 1 A 1 H H3XD 0.6398 0.4176 0.8202 0.064 Uiso d PR 0.436(2) 1 A 2 H H3XE 0.6584 0.2240 0.7942 0.064 Uiso d PR 0.436(2) 1 A 2 H H3XF 0.5567 0.3304 0.7329 0.064 Uiso d PR 0.436(2) 1 A 2 C C4X 0.6751(2) 0.2524(3) 0.62857(15) 0.0420(5) Uani d . 1 1 . . H H4XA 0.6664 0.2738 0.5670 0.063 Uiso calc PR 0.564(2) 1 A 1 H H4XB 0.6493 0.1361 0.6340 0.063 Uiso calc PR 0.564(2) 1 A 1 H H4XC 0.7504 0.2613 0.6661 0.063 Uiso calc PR 0.564(2) 1 A 1 H H4XD 0.7110 0.2784 0.5876 0.063 Uiso d PR 0.436(2) 1 A 2 H H4XE 0.5984 0.2467 0.5959 0.063 Uiso d PR 0.436(2) 1 A 2 H H4XF 0.7003 0.1410 0.6574 0.063 Uiso d PR 0.436(2) 1 A 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 N1 0.0230(7) 0.0230(8) 0.0221(7) 0.0006(6) 0.0109(6) 0.0004(6) C2 0.0215(9) 0.0196(8) 0.0211(8) -0.0015(7) 0.0077(7) -0.0011(6) N3 0.0258(8) 0.0211(7) 0.0216(7) 0.0026(6) 0.0114(6) 0.0001(6) C4 0.0232(9) 0.0204(8) 0.0214(8) -0.0005(7) 0.0095(7) -0.0014(6) C5 0.0198(8) 0.0203(8) 0.0207(8) 0.0002(7) 0.0084(6) -0.0026(6) C6 0.0196(8) 0.0210(8) 0.0210(8) -0.0020(7) 0.0094(6) -0.0030(6) N21 0.0393(10) 0.0307(9) 0.0243(8) 0.0125(8) 0.0139(7) 0.0064(7) N41 0.0402(10) 0.0290(9) 0.0251(8) 0.0151(8) 0.0195(7) 0.0060(7) C51 0.0235(9) 0.0230(9) 0.0193(7) 0.0026(7) 0.0123(7) -0.0003(6) C52 0.0266(9) 0.0217(9) 0.0283(9) 0.0002(7) 0.0074(7) -0.0041(7) C53 0.0249(9) 0.0294(10) 0.0258(9) 0.0018(8) 0.0043(7) -0.0020(7) C54 0.0299(10) 0.0242(9) 0.0208(8) 0.0079(7) 0.0128(7) 0.0032(6) C55 0.0322(10) 0.0208(9) 0.0253(8) -0.0016(8) 0.0130(7) -0.0020(7) C56 0.0239(9) 0.0253(9) 0.0222(8) -0.0009(7) 0.0078(7) -0.0007(7) C61 0.0261(9) 0.0259(9) 0.0238(8) 0.0025(7) 0.0146(7) -0.0009(7) C62 0.0328(10) 0.0286(9) 0.0236(8) 0.0016(8) 0.0116(8) -0.0042(7) Cl1 0.0424(3) 0.0295(3) 0.0305(3) 0.0146(2) 0.0112(2) 0.00520(18) O1X 0.0654(11) 0.0270(8) 0.0522(9) 0.0125(7) 0.0339(8) 0.0133(7) S2X 0.0248(5) 0.0347(5) 0.0338(5) 0.0031(4) 0.0107(4) -0.0009(3) S2X' 0.0283(6) 0.0236(6) 0.0388(6) 0.0011(4) 0.0165(5) 0.0017(4) C3X 0.0582(15) 0.0386(12) 0.0420(11) -0.0001(11) 0.0307(11) 0.0036(9) C4X 0.0536(14) 0.0348(12) 0.0468(12) -0.0014(10) 0.0293(11) -0.0073(9) 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 C2 N1 C6 115.85(14) N1 C2 N3 126.91(16) N1 C2 N21 116.33(15) N3 C2 N21 116.76(16) C2 N3 C4 116.32(14) N41 C4 N3 116.42(16) N41 C4 C5 121.73(16) N3 C4 C5 121.85(15) C6 C5 C4 115.95(16) C6 C5 C51 122.58(15) C4 C5 C51 121.42(14) N1 C6 C5 123.08(15) N1 C6 C61 114.55(14) C5 C6 C61 122.35(16) C2 N21 H211 117.0(16) C2 N21 H212 120.8(18) H211 N21 H212 121(2) C4 N41 H411 117.5(17) C4 N41 H412 119.7(16) H411 N41 H412 120(2) C56 C51 C52 118.23(16) C56 C51 C5 120.59(15) C52 C51 C5 121.15(16) C53 C52 C51 121.39(17) C53 C52 H52 119.3 C51 C52 H52 119.3 C54 C53 C52 118.50(17) C54 C53 H53 120.8 C52 C53 H53 120.8 C55 C54 C53 121.85(17) C55 C54 Cl1 118.87(14) C53 C54 Cl1 119.29(14) C54 C55 C56 118.70(17) C54 C55 H55 120.7 C56 C55 H55 120.7 C55 C56 C51 121.30(17) C55 C56 H56 119.4 C51 C56 H56 119.4 C6 C61 C62 110.68(15) C6 C61 H61A 109.5 C62 C61 H61A 109.5 C6 C61 H61B 109.5 C62 C61 H61B 109.5 H61A C61 H61B 108.1 C61 C62 H62A 109.5 C61 C62 H62B 109.5 H62A C62 H62B 109.5 C61 C62 H62C 109.5 H62A C62 H62C 109.5 H62B C62 H62C 109.5 S2X' O1X S2X 52.93(8) O1X S2X C3X 108.09(12) O1X S2X C4X 106.47(11) C3X S2X C4X 98.94(12) O1X S2X H3XF 128.2 C4X S2X H3XF 111.8 O1X S2X H4XE 125.6 C3X S2X H4XE 111.9 H3XF S2X H4XE 105.2 O1X S2X' C3X 109.23(12) O1X S2X' C4X 107.77(12) C3X S2X' C4X 99.13(12) S2X' C3X H3XA 123.4 S2X C3X H3XA 109.5 S2X' C3X H3XB 65.1 S2X C3X H3XB 109.5 H3XA C3X H3XB 109.5 S2X' C3X H3XC 125.8 S2X C3X H3XC 109.5 H3XA C3X H3XC 109.5 H3XB C3X H3XC 109.5 S2X' C3X H3XD 109.6 S2X C3X H3XD 123.4 H3XB C3X H3XD 76.3 H3XC C3X H3XD 121.5 S2X' C3X H3XE 109.4 S2X C3X H3XE 125.9 H3XA C3X H3XE 121.7 H3XB C3X H3XE 70.4 H3XD C3X H3XE 109.4 S2X' C3X H3XF 109.4 S2X C3X H3XF 65.0 H3XA C3X H3XF 76.4 H3XB C3X H3XF 173.4 H3XC C3X H3XF 70.4 H3XD C3X H3XF 109.5 H3XE C3X H3XF 109.5 S2X' C4X H4XA 123.5 S2X C4X H4XA 109.5 S2X' C4X H4XB 125.5 S2X C4X H4XB 109.5 H4XA C4X H4XB 109.5 S2X' C4X H4XC 65.8 S2X C4X H4XC 109.5 H4XA C4X H4XC 109.5 H4XB C4X H4XC 109.5 S2X' C4X H4XD 109.3 S2X C4X H4XD 123.2 H4XB C4X H4XD 122.2 H4XC C4X H4XD 75.4 S2X' C4X H4XE 109.7 S2X C4X H4XE 66.1 H4XA C4X H4XE 75.3 H4XB C4X H4XE 70.3 H4XC C4X H4XE 174.6 H4XD C4X H4XE 109.4 S2X' C4X H4XF 109.4 S2X C4X H4XF 125.7 H4XA C4X H4XF 121.9 H4XC C4X H4XF 70.3 H4XD C4X H4XF 109.5 H4XE C4X H4XF 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.340(2) N1 C6 1.350(2) C2 N3 1.345(2) C2 N21 1.357(2) N3 C4 1.345(2) C4 N41 1.346(2) C4 C5 1.422(2) C5 C6 1.386(2) C5 C51 1.492(2) C6 C61 1.512(2) N21 H211 0.85(2) N21 H212 0.85(3) N41 H411 0.84(3) N41 H412 0.88(3) C51 C56 1.388(3) C51 C52 1.396(3) C52 C53 1.386(3) C52 H52 0.9500 C53 C54 1.381(3) C53 H53 0.9500 C54 C55 1.379(3) C54 Cl1 1.7494(18) C55 C56 1.389(3) C55 H55 0.9500 C56 H56 0.9500 C61 C62 1.527(3) C61 H61A 0.9900 C61 H61B 0.9900 C62 H62A 0.9800 C62 H62B 0.9800 C62 H62C 0.9800 O1X S2X' 1.4689(18) O1X S2X 1.4922(19) S2X C3X 1.746(2) S2X C4X 1.777(2) S2X H3XF 1.6009 S2X H4XE 1.6447 S2X' C3X 1.746(2) S2X' C4X 1.773(2) C3X H3XA 0.9800 C3X H3XB 0.9800 C3X H3XC 0.9800 C3X H3XD 0.9800 C3X H3XE 0.9795 C3X H3XF 0.9800 C4X H4XA 0.9800 C4X H4XB 0.9800 C4X H4XC 0.9800 C4X H4XD 0.9799 C4X H4XE 0.9799 C4X H4XF 0.9796 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 N21 H211 Cl1 4_575 0.85(2) 2.72(3) 3.5607(18) 170(2) N21 H212 O1X 3_676 0.85(3) 2.14(3) 2.958(2) 164(2) N41 H411 N3 3_676 0.84(3) 2.26(3) 3.102(2) 174(2) N41 H412 O1X . 0.88(3) 2.22(3) 2.921(2) 137(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 C6 N1 C2 N3 -1.2(3) C6 N1 C2 N21 178.47(16) N1 C2 N3 C4 1.3(3) N21 C2 N3 C4 -178.39(16) C2 N3 C4 N41 -178.96(16) C2 N3 C4 C5 0.4(3) N41 C4 C5 C6 177.37(17) N3 C4 C5 C6 -2.0(3) N41 C4 C5 C51 -0.1(3) N3 C4 C5 C51 -179.41(16) C2 N1 C6 C5 -0.6(2) C2 N1 C6 C61 177.54(15) C4 C5 C6 N1 2.1(3) C51 C5 C6 N1 179.49(16) C4 C5 C6 C61 -175.92(16) C51 C5 C6 C61 1.5(3) C6 C5 C51 C56 -74.1(2) C4 C5 C51 C56 103.2(2) C6 C5 C51 C52 103.9(2) C4 C5 C51 C52 -78.8(2) C56 C51 C52 C53 1.5(3) C5 C51 C52 C53 -176.56(16) C51 C52 C53 C54 0.2(3) C52 C53 C54 C55 -1.1(3) C52 C53 C54 Cl1 178.77(14) C53 C54 C55 C56 0.2(3) Cl1 C54 C55 C56 -179.69(13) C54 C55 C56 C51 1.6(3) C52 C51 C56 C55 -2.5(3) C5 C51 C56 C55 175.62(16) N1 C6 C61 C62 -76.67(19) C5 C6 C61 C62 101.5(2) S2X' O1X S2X C3X 51.88(11) S2X' O1X S2X C4X -53.62(11) S2X O1X S2X' C3X -52.39(12) S2X O1X S2X' C4X 54.37(11) O1X S2X' C3X S2X 50.52(11) C4X S2X' C3X S2X -62.03(11) O1X S2X C3X S2X' -49.00(10) C4X S2X C3X S2X' 61.70(11) O1X S2X' C4X S2X -52.08(11) C3X S2X' C4X S2X 61.61(11) O1X S2X C4X S2X' 50.45(10) C3X S2X C4X S2X' -61.53(11) _cod_database_fobs_code 2018301 _journal_paper_doi 10.1107/S0108270111038868