#------------------------------------------------------------------------------ #$Date: 2015-08-26 04:42:05 +0300 (Wed, 26 Aug 2015) $ #$Revision: 153656 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/02/00/2020090.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_2020090 loop_ _publ_author_name 'Gerhardt, Valeska' 'Bolte, Michael' _publ_section_title ; Cocrystals of 2,6-dichloroaniline and 2,6-dichlorophenol plus three new pseudopolymorphs of their coformers ; _journal_coeditor_code SK3598 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first ; ; _journal_paper_doi 10.1107/S2053229615015119 _journal_volume 71 _journal_year 2015 _chemical_formula_iupac 'C4 H7 N5, C5 H9 N O' _chemical_formula_moiety 'C4 H7 N5, C5 H9 N O' _chemical_formula_sum 'C9 H16 N6 O' _chemical_formula_weight 224.28 _chemical_name_systematic ; 2,4-Diamino-6-methyl-1,3,5-triazine--N-methylpyrrolidin-2-one (1/1) ; _space_group_IT_number 43 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'F 2 -2d' _symmetry_space_group_name_H-M 'F d d 2' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 16 _cell_length_a 23.178(2) _cell_length_b 26.3327(17) _cell_length_c 7.3428(5) _cell_measurement_reflns_used 15487 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.97 _cell_measurement_theta_min 3.515 _cell_volume 4481.6(6) _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 (Macrae et al., 2008) and XP in SHELXTL-Plus (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 0.997 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Stoe IPDS II two-circle' _diffrn_measurement_method \w _diffrn_radiation_monochromator 'Genix 3D multilayer optics' _diffrn_radiation_source 'Genix 3D I\mS microfocus X-ray source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1040 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 27934 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.64 _diffrn_reflns_theta_min 3.52 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 0.776 _exptl_absorpt_correction_T_min 0.623 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (X-AREA; Stoe & Cie, 2001) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1920 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.156 _refine_diff_density_min -0.203 _refine_ls_abs_structure_details - _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.216 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 159 _refine_ls_number_reflns 1147 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.215 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0519 _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^)+(0.0505P)^2^+1.9967P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1007 _refine_ls_wR_factor_ref 0.1034 _reflns_number_gt 1050 _reflns_number_total 1147 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL II in Fdd2 CELL 0.71073 23.1785 26.3327 7.3428 90.000 90.000 90.000 ZERR 16.00 0.0021 0.0017 0.0005 0.000 0.000 0.000 LATT -4 SYMM -X, -Y, Z SYMM 0.25+X, 0.25-Y, 0.25+Z SYMM 0.25-X, 0.25+Y, 0.25+Z SFAC C H N O UNIT 144 256 96 16 ACTA 50 SIZE 0.19 0.10 0.14 REM farbloser Block TEMP -100 HTAB N2 N3_$1 HTAB N2 N5_$2 HTAB N4 N1_$3 HTAB N4 O2X EQIV_$1 -x+1, -y+1, z EQIV_$2 x-1/4, -y+3/4, z+1/4 EQIV_$3 x+1/4, -y+3/4, z-1/4 MPLA N1_$1 C2_$1 N2_$1 N3_$1 C4_$1 N4_$1 N5_$1 C6_$1 C61_$1 MPLA N1 > C61 MPLA N1X > C5X MERG 3 L.S. 15 BOND $H CONF FMAP 2 PLAN 10 WGHT 0.050500 1.996700 FVAR 0.05159 N1 3 0.495941 0.366820 0.573018 11.00000 0.01820 0.01927 = 0.03079 0.00165 0.00569 0.00204 C2 1 0.498449 0.418117 0.564199 11.00000 0.01738 0.02316 = 0.01949 -0.00040 -0.00174 0.00061 N2 3 0.451299 0.443904 0.608999 11.00000 0.01828 0.01665 = 0.03965 0.00134 0.00523 -0.00229 H21 2 0.450083 0.479576 0.595161 11.00000 -1.20000 H22 2 0.421637 0.425781 0.627051 11.00000 -1.20000 N3 3 0.545623 0.444732 0.515131 11.00000 0.01543 0.01859 = 0.02875 0.00150 0.00121 -0.00020 C4 1 0.592065 0.416916 0.475332 11.00000 0.01500 0.02292 = 0.02179 -0.00103 -0.00064 -0.00027 N4 3 0.639876 0.440889 0.423050 11.00000 0.01495 0.01615 = 0.03890 0.00079 0.00580 0.00213 H41 2 0.669226 0.424204 0.388455 11.00000 -1.20000 H42 2 0.639238 0.473850 0.405990 11.00000 -1.20000 N5 3 0.594454 0.365396 0.481184 11.00000 0.01953 0.01594 = 0.03187 0.00088 0.00213 0.00208 C6 1 0.544849 0.343112 0.530527 11.00000 0.02019 0.02194 = 0.02602 0.00000 -0.00251 -0.00016 C61 1 0.545026 0.286663 0.539210 11.00000 0.02820 0.02182 = 0.06296 -0.00364 0.01165 0.00130 AFIX 137 H61A 2 0.552297 0.275765 0.664743 11.00000 -1.50000 H61B 2 0.575397 0.273367 0.459538 11.00000 -1.50000 H61C 2 0.507500 0.273675 0.499069 11.00000 -1.50000 AFIX 0 N1X 3 0.589144 0.585710 0.168093 11.00000 0.02612 0.02920 = 0.03616 0.00570 0.00126 -0.00249 C1X 1 0.553516 0.542284 0.129033 11.00000 0.03310 0.03529 = 0.04717 -0.00207 0.00194 -0.00590 AFIX 137 H1X1 2 0.574208 0.511187 0.162337 11.00000 -1.50000 H1X2 2 0.544397 0.541579 -0.001265 11.00000 -1.50000 H1X3 2 0.517686 0.544521 0.199434 11.00000 -1.50000 AFIX 0 C2X 1 0.641754 0.583086 0.244570 11.00000 0.02865 0.03291 = 0.03097 0.00519 0.00523 0.00234 O2X 4 0.664698 0.544045 0.298980 11.00000 0.03503 0.03104 = 0.06210 0.01414 -0.00198 0.00700 C3X 1 0.667237 0.635281 0.247015 11.00000 0.03037 0.03286 = 0.03149 0.00443 0.00155 -0.00184 AFIX 23 H3X1 2 0.700317 0.637437 0.162078 11.00000 -1.20000 H3X2 2 0.680752 0.644077 0.370962 11.00000 -1.20000 AFIX 0 C4X 1 0.619147 0.670995 0.187534 11.00000 0.04073 0.02605 = 0.03299 0.00270 0.00350 0.00082 AFIX 23 H4X1 2 0.633008 0.694579 0.092085 11.00000 -1.20000 H4X2 2 0.604858 0.691115 0.292116 11.00000 -1.20000 AFIX 0 C5X 1 0.571346 0.636441 0.112810 11.00000 0.02971 0.03188 = 0.03262 0.00786 0.00275 0.00764 AFIX 23 H5X1 2 0.533461 0.645344 0.166260 11.00000 -1.20000 H5X2 2 0.568790 0.639042 -0.021451 11.00000 -1.20000 HKLF 4 REM II in Fdd2 REM R1 = 0.0519 for 1050 Fo > 4sig(Fo) and 0.0613 for all 1147 data REM 159 parameters refined using 1 restraints END WGHT 0.0505 1.9967 ; _cod_data_source_file sk3598sup1.cif _cod_data_source_block II _cod_original_cell_volume 4481.7(6) _cod_database_code 2020090 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' 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 N N1 0.49594(12) 0.36682(10) 0.5730(4) 0.0228(7) Uani d . 1 1 C C2 0.49845(14) 0.41812(12) 0.5642(5) 0.0200(7) Uani d . 1 1 N N2 0.45130(13) 0.44390(12) 0.6090(5) 0.0249(7) Uani d . 1 1 H H21 0.4501(17) 0.4796(17) 0.595(5) 0.030 Uiso d . 1 1 H H22 0.4216(18) 0.4258(16) 0.627(6) 0.030 Uiso d . 1 1 N N3 0.54562(12) 0.44473(10) 0.5151(5) 0.0209(6) Uani d . 1 1 C C4 0.59207(14) 0.41692(12) 0.4753(5) 0.0199(8) Uani d . 1 1 N N4 0.63988(13) 0.44089(12) 0.4230(5) 0.0233(7) Uani d . 1 1 H H41 0.6692(19) 0.4242(16) 0.388(6) 0.028 Uiso d . 1 1 H H42 0.6392(16) 0.4738(16) 0.406(6) 0.028 Uiso d . 1 1 N N5 0.59445(12) 0.36540(10) 0.4812(4) 0.0224(7) Uani d . 1 1 C C6 0.54485(15) 0.34311(12) 0.5305(6) 0.0227(8) Uani d . 1 1 C C61 0.54503(18) 0.28666(13) 0.5392(7) 0.0377(11) Uani d . 1 1 H H61A 0.5523 0.2758 0.6647 0.056 Uiso calc R 1 1 H H61B 0.5754 0.2734 0.4595 0.056 Uiso calc R 1 1 H H61C 0.5075 0.2737 0.4991 0.056 Uiso calc R 1 1 N N1X 0.58914(12) 0.58571(12) 0.1681(5) 0.0305(8) Uani d . 1 1 C C1X 0.55352(18) 0.54228(16) 0.1290(7) 0.0385(10) Uani d . 1 1 H H1X1 0.5742 0.5112 0.1623 0.058 Uiso calc R 1 1 H H1X2 0.5444 0.5416 -0.0013 0.058 Uiso calc R 1 1 H H1X3 0.5177 0.5445 0.1994 0.058 Uiso calc R 1 1 C C2X 0.64175(16) 0.58309(15) 0.2446(6) 0.0308(9) Uani d . 1 1 O O2X 0.66470(12) 0.54405(11) 0.2990(5) 0.0427(8) Uani d . 1 1 C C3X 0.66724(16) 0.63528(14) 0.2470(6) 0.0316(9) Uani d . 1 1 H H3X1 0.7003 0.6374 0.1621 0.038 Uiso calc R 1 1 H H3X2 0.6808 0.6441 0.3710 0.038 Uiso calc R 1 1 C C4X 0.61915(17) 0.67100(14) 0.1875(6) 0.0333(9) Uani d . 1 1 H H4X1 0.6330 0.6946 0.0921 0.040 Uiso calc R 1 1 H H4X2 0.6049 0.6911 0.2921 0.040 Uiso calc R 1 1 C C5X 0.57135(16) 0.63644(14) 0.1128(6) 0.0314(9) Uani d . 1 1 H H5X1 0.5335 0.6453 0.1663 0.038 Uiso calc R 1 1 H H5X2 0.5688 0.6390 -0.0215 0.038 Uiso calc R 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 N1 0.0182(14) 0.0193(14) 0.0308(18) 0.0020(12) 0.0057(12) 0.0016(14) C2 0.0174(15) 0.0232(17) 0.0195(17) 0.0006(14) -0.0017(13) -0.0004(16) N2 0.0183(15) 0.0167(15) 0.0396(19) -0.0023(13) 0.0052(15) 0.0013(14) N3 0.0154(12) 0.0186(13) 0.0288(15) -0.0002(12) 0.0012(12) 0.0015(14) C4 0.0150(15) 0.0229(18) 0.0218(19) -0.0003(14) -0.0006(14) -0.0010(16) N4 0.0149(14) 0.0161(14) 0.0389(19) 0.0021(13) 0.0058(14) 0.0008(13) N5 0.0195(15) 0.0159(15) 0.0319(18) 0.0021(11) 0.0021(13) 0.0009(14) C6 0.0202(15) 0.0219(16) 0.0260(19) -0.0002(15) -0.0025(14) 0.0000(16) C61 0.0282(18) 0.0218(18) 0.063(3) 0.0013(17) 0.012(2) -0.004(2) N1X 0.0261(16) 0.0292(17) 0.0362(19) -0.0025(13) 0.0013(16) 0.0057(15) C1X 0.033(2) 0.035(2) 0.047(3) -0.0059(18) 0.002(2) -0.002(2) C2X 0.0286(19) 0.033(2) 0.031(2) 0.0023(17) 0.0052(18) 0.0052(18) O2X 0.0350(15) 0.0310(15) 0.062(2) 0.0070(12) -0.0020(14) 0.0141(15) C3X 0.030(2) 0.033(2) 0.031(2) -0.0018(17) 0.0016(18) 0.0044(18) C4X 0.041(2) 0.0260(19) 0.033(2) 0.0008(18) 0.0035(18) 0.0027(17) C5X 0.0297(19) 0.032(2) 0.033(2) 0.0076(17) 0.0028(18) 0.0079(18) 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C6 N1 C2 114.8(3) N2 C2 N3 117.9(3) N2 C2 N1 117.6(3) N3 C2 N1 124.5(3) C2 N2 H21 120(2) C2 N2 H22 115(3) H21 N2 H22 124(4) C4 N3 C2 115.3(3) N4 C4 N3 118.3(3) N4 C4 N5 116.7(3) N3 C4 N5 125.0(3) C4 N4 H41 121(3) C4 N4 H42 120(3) H41 N4 H42 119(4) C6 N5 C4 114.2(3) N1 C6 N5 126.0(3) N1 C6 C61 117.4(3) N5 C6 C61 116.5(3) C6 C61 H61A 109.5 C6 C61 H61B 109.5 H61A C61 H61B 109.5 C6 C61 H61C 109.5 H61A C61 H61C 109.5 H61B C61 H61C 109.5 C2X N1X C1X 124.3(3) C2X N1X C5X 114.9(3) C1X N1X C5X 120.7(3) N1X C1X H1X1 109.5 N1X C1X H1X2 109.5 H1X1 C1X H1X2 109.5 N1X C1X H1X3 109.5 H1X1 C1X H1X3 109.5 H1X2 C1X H1X3 109.5 O2X C2X N1X 125.0(4) O2X C2X C3X 126.6(4) N1X C2X C3X 108.4(3) C2X C3X C4X 106.0(3) C2X C3X H3X1 110.5 C4X C3X H3X1 110.5 C2X C3X H3X2 110.5 C4X C3X H3X2 110.5 H3X1 C3X H3X2 108.7 C3X C4X C5X 105.4(3) C3X C4X H4X1 110.7 C5X C4X H4X1 110.7 C3X C4X H4X2 110.7 C5X C4X H4X2 110.7 H4X1 C4X H4X2 108.8 N1X C5X C4X 103.9(3) N1X C5X H5X1 111.0 C4X C5X H5X1 111.0 N1X C5X H5X2 111.0 C4X C5X H5X2 111.0 H5X1 C5X H5X2 109.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C6 1.331(4) N1 C2 1.354(4) C2 N2 1.328(5) C2 N3 1.348(4) N2 H21 0.95(4) N2 H22 0.85(4) N3 C4 1.334(4) C4 N4 1.332(4) C4 N5 1.358(4) N4 H41 0.85(5) N4 H42 0.88(4) N5 C6 1.341(4) C6 C61 1.488(5) C61 H61A 0.9800 C61 H61B 0.9800 C61 H61C 0.9800 N1X C2X 1.344(5) N1X C1X 1.439(5) N1X C5X 1.456(5) C1X H1X1 0.9800 C1X H1X2 0.9800 C1X H1X3 0.9800 C2X O2X 1.224(5) C2X C3X 1.496(5) C3X C4X 1.522(5) C3X H3X1 0.9900 C3X H3X2 0.9900 C4X C5X 1.535(6) C4X H4X1 0.9900 C4X H4X2 0.9900 C5X H5X1 0.9900 C5X H5X2 0.9900 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 N2 H21 N3 2_665 0.95(4) 2.08(4) 3.013(4) 169(4) N2 H22 N5 15_455 0.85(4) 2.23(5) 3.062(4) 168(4) N4 H41 N1 7_554 0.85(5) 2.14(5) 2.982(4) 175(4) N4 H42 O2X . 0.88(4) 2.09(4) 2.922(4) 157(4) 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 N2 -178.6(4) C6 N1 C2 N3 0.7(6) N2 C2 N3 C4 178.6(3) N1 C2 N3 C4 -0.6(6) C2 N3 C4 N4 179.0(3) C2 N3 C4 N5 0.0(6) N4 C4 N5 C6 -178.5(3) N3 C4 N5 C6 0.4(5) C2 N1 C6 N5 -0.1(6) C2 N1 C6 C61 179.5(4) C4 N5 C6 N1 -0.4(6) C4 N5 C6 C61 180.0(4) C1X N1X C2X O2X -4.0(6) C5X N1X C2X O2X -179.5(4) C1X N1X C2X C3X 174.7(4) C5X N1X C2X C3X -0.8(5) O2X C2X C3X C4X -173.0(4) N1X C2X C3X C4X 8.3(4) C2X C3X C4X C5X -12.1(4) C2X N1X C5X C4X -6.9(5) C1X N1X C5X C4X 177.4(4) C3X C4X C5X N1X 11.4(4) _cod_database_fobs_code 2020090