#------------------------------------------------------------------------------ #$Date: 2015-08-26 04:42:05 +0300 (Wed, 26 Aug 2015) $ #$Revision: 153656 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/02/00/2020091.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_2020091 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 'C6 H4 Cl2 O, C4 H7 N5 ' _chemical_formula_moiety 'C6 H4 Cl2 O, C4 H7 N5 ' _chemical_formula_sum 'C10 H11 Cl2 N5 O' _chemical_formula_weight 288.14 _chemical_name_systematic ; 2,4-Diamino-6-methyl-1,3,5-triazine--2,6-dichlorophenol (1/1) ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _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_method SHELXL-97 _cell_angle_alpha 93.929(11) _cell_angle_beta 96.214(11) _cell_angle_gamma 100.121(11) _cell_formula_units_Z 2 _cell_length_a 5.0318(7) _cell_length_b 8.5779(11) _cell_length_c 15.008(2) _cell_measurement_reflns_used 2942 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 26.04 _cell_measurement_theta_min 3.49 _cell_volume 631.41(15) _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 0.995 _diffrn_measured_fraction_theta_max 0.989 _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 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 5126 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.61 _diffrn_reflns_theta_min 3.49 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.509 _exptl_absorpt_correction_T_max 0.872 _exptl_absorpt_correction_T_min 0.719 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (X-AREA; Stoe & Cie, 2001) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 296 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.189 _refine_diff_density_min -0.213 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 180 _refine_ls_number_reflns 2354 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0332 _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^)+(0.0448P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0766 _refine_ls_wR_factor_ref 0.0809 _reflns_number_gt 1864 _reflns_number_total 2354 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL III in P-1 CELL 0.71073 5.0318 8.5779 15.0080 93.929 96.214 100.121 ZERR 2.00 0.0007 0.0011 0.0020 0.011 0.011 0.011 LATT 1 SFAC C H N O CL UNIT 20 22 10 2 4 ACTA 50 REM farblos Nadel SIZE 0.122 0.191 0.063 TEMP -100 HTAB N2B O1A_$1 HTAB N2B N1B_$2 HTAB N4B N3B_$1 HTAB O1A N5B_$3 RTAB DIST N4B Cl6A RTAB ANGL N4B H4B1 Cl6A RTAB DIST H4B1 Cl6A RTAB DIST N4B O1A RTAB ANGL N4B H4B1 O1A RTAB DIST H4B1 O1A EQIV_$1 -x+1, -y+1, -z+1 EQIV_$2 -x+2, -y, -z+1 EQIV_$3 x-1, y, z MPLA N1B > C61B MPLA C1A > Cl6A MPLA C4B N4B Cl6A L.S. 8 BOND $H CONF FMAP 2 PLAN 10 WGHT 0.044800 FVAR 1.03079 0.71257 N1B 3 0.977112 0.161484 0.422593 11.00000 0.03052 0.01975 = 0.02998 0.00202 0.00668 0.00562 C2B 1 0.827094 0.215417 0.483690 11.00000 0.02617 0.01878 = 0.02804 0.00164 0.00323 0.00198 N2B 3 0.787633 0.131595 0.553893 11.00000 0.04659 0.02483 = 0.03356 0.00927 0.01452 0.01502 H2B1 2 0.705915 0.168340 0.593652 11.00000 -1.20000 H2B2 2 0.853466 0.048124 0.560096 11.00000 -1.20000 N3B 3 0.715018 0.345832 0.478182 11.00000 0.02442 0.02208 = 0.02835 0.00388 0.00384 0.00478 C4B 1 0.772764 0.429051 0.408284 11.00000 0.01921 0.02150 = 0.02565 0.00255 -0.00131 0.00159 N4B 3 0.663281 0.557675 0.398152 11.00000 0.03138 0.03008 = 0.03190 0.01264 0.00915 0.01306 H4B1 2 0.679496 0.602853 0.351001 11.00000 -1.20000 H4B2 2 0.544973 0.578546 0.433200 11.00000 -1.20000 N5B 3 0.934050 0.390393 0.346893 11.00000 0.02456 0.02432 = 0.02820 0.00364 0.00495 0.00378 C6B 1 1.025520 0.255208 0.356882 11.00000 0.02358 0.02012 = 0.02844 0.00041 0.00140 0.00150 C61B 1 1.194157 0.205520 0.288373 11.00000 0.03543 0.02790 = 0.03855 0.00267 0.01400 0.00658 AFIX 137 PART 1 H6B1 2 1.322091 0.143442 0.315787 21.00000 -1.50000 H6B2 2 1.295579 0.300035 0.265931 21.00000 -1.50000 H6B3 2 1.075849 0.140365 0.238287 21.00000 -1.50000 AFIX 137 PART 2 H6BA 2 1.385568 0.253198 0.306940 -21.00000 -1.50000 H6BB 2 1.134189 0.241239 0.230156 -21.00000 -1.50000 H6BC 2 1.173762 0.089404 0.282908 -21.00000 -1.50000 AFIX 0 PART 0 C1A 1 0.152581 0.681849 0.190304 11.00000 0.02709 0.02666 = 0.02753 0.00464 0.00651 0.00991 O1A 4 0.189559 0.628542 0.271282 11.00000 0.03199 0.03264 = 0.02948 0.01067 -0.00152 -0.00319 H1A 2 0.083339 0.544588 0.284113 11.00000 -1.50000 C2A 1 -0.060604 0.622422 0.123896 11.00000 0.03301 0.03644 = 0.02983 0.00354 0.00550 0.00955 CL2A 5 -0.305873 0.464659 0.145670 11.00000 0.03667 0.05326 = 0.03948 0.00287 -0.00457 -0.00674 C3A 1 -0.087358 0.685107 0.041473 11.00000 0.05095 0.05909 = 0.02961 0.00591 -0.00348 0.01431 AFIX 43 H3A 2 -0.235298 0.640866 -0.003024 11.00000 -1.20000 AFIX 0 C4A 1 0.102934 0.812143 0.024919 11.00000 0.07243 0.06302 = 0.03346 0.02233 0.00779 0.01489 AFIX 43 H4A 2 0.085769 0.856327 -0.031298 11.00000 -1.20000 AFIX 0 C5A 1 0.317512 0.875704 0.088901 11.00000 0.05877 0.04375 = 0.04328 0.01786 0.01910 0.00724 AFIX 43 H5A 2 0.448245 0.963837 0.077314 11.00000 -1.20000 AFIX 0 C6A 1 0.341675 0.810458 0.170210 11.00000 0.03157 0.03026 = 0.03492 0.00494 0.00913 0.00795 CL6A 5 0.612992 0.888851 0.251702 11.00000 0.03482 0.03385 = 0.04911 0.00501 0.00661 -0.00380 HKLF 4 REM III in P-1 REM R1 = 0.0332 for 1864 Fo > 4sig(Fo) and 0.0484 for all 2354 data REM 180 parameters refined using 0 restraints END WGHT 0.0448 0.0000 REM Highest difference peak 0.189, deepest hole -0.213, 1-sigma level 0.043 ; _cod_data_source_file sk3598sup1.cif _cod_data_source_block III _cod_database_code 2020091 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 N1B 0.9771(3) 0.16148(16) 0.42259(10) 0.0264(3) Uani d . 1 1 . . C C2B 0.8271(4) 0.21542(19) 0.48369(12) 0.0246(4) Uani d . 1 1 . . N N2B 0.7876(4) 0.1316(2) 0.55389(12) 0.0329(4) Uani d . 1 1 . . H H2B1 0.706(5) 0.168(3) 0.5937(16) 0.040 Uiso d . 1 1 . . H H2B2 0.853(5) 0.048(3) 0.5601(16) 0.040 Uiso d . 1 1 . . N N3B 0.7150(3) 0.34583(16) 0.47818(10) 0.0248(3) Uani d . 1 1 . . C C4B 0.7728(4) 0.42905(19) 0.40828(11) 0.0227(4) Uani d . 1 1 . . N N4B 0.6633(4) 0.55767(19) 0.39815(12) 0.0294(4) Uani d . 1 1 . . H H4B1 0.679(5) 0.603(3) 0.3510(16) 0.035 Uiso d . 1 1 . . H H4B2 0.545(5) 0.579(3) 0.4332(16) 0.035 Uiso d . 1 1 . . N N5B 0.9340(3) 0.39039(16) 0.34689(10) 0.0256(3) Uani d . 1 1 . . C C6B 1.0255(4) 0.2552(2) 0.35688(12) 0.0246(4) Uani d . 1 1 . . C C61B 1.1942(4) 0.2055(2) 0.28837(14) 0.0332(5) Uani d . 1 1 . . H H6B1 1.3221 0.1434 0.3158 0.050 Uiso calc PR 0.71(2) 1 A 1 H H6B2 1.2956 0.3000 0.2659 0.050 Uiso calc PR 0.71(2) 1 A 1 H H6B3 1.0758 0.1404 0.2383 0.050 Uiso calc PR 0.71(2) 1 A 1 H H6BA 1.3856 0.2532 0.3069 0.050 Uiso calc PR 0.29(2) 1 A 2 H H6BB 1.1342 0.2412 0.2302 0.050 Uiso calc PR 0.29(2) 1 A 2 H H6BC 1.1738 0.0894 0.2829 0.050 Uiso calc PR 0.29(2) 1 A 2 C C1A 0.1526(4) 0.6818(2) 0.19030(12) 0.0261(4) Uani d . 1 1 . . O O1A 0.1896(3) 0.62854(16) 0.27128(9) 0.0325(3) Uani d . 1 1 . . H H1A 0.083(6) 0.545(3) 0.2841(17) 0.049 Uiso d . 1 1 . . C C2A -0.0606(4) 0.6224(2) 0.12390(13) 0.0326(4) Uani d . 1 1 . . Cl Cl2A -0.30587(12) 0.46466(7) 0.14567(4) 0.04572(17) Uani d . 1 1 . . C C3A -0.0874(5) 0.6851(3) 0.04147(15) 0.0466(6) Uani d . 1 1 . . H H3A -0.2353 0.6409 -0.0030 0.056 Uiso calc R 1 1 . . C C4A 0.1029(6) 0.8121(3) 0.02492(16) 0.0551(7) Uani d . 1 1 . . H H4A 0.0858 0.8563 -0.0313 0.066 Uiso calc R 1 1 . . C C5A 0.3175(6) 0.8757(3) 0.08890(16) 0.0473(6) Uani d . 1 1 . . H H5A 0.4482 0.9638 0.0773 0.057 Uiso calc R 1 1 . . C C6A 0.3417(4) 0.8105(2) 0.17021(13) 0.0315(4) Uani d . 1 1 . . Cl Cl6A 0.61299(11) 0.88885(6) 0.25170(4) 0.04033(16) Uani 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 N1B 0.0305(9) 0.0197(7) 0.0300(8) 0.0056(6) 0.0067(7) 0.0020(6) C2B 0.0262(10) 0.0188(8) 0.0280(9) 0.0020(7) 0.0032(8) 0.0016(7) N2B 0.0466(12) 0.0248(8) 0.0336(9) 0.0150(8) 0.0145(8) 0.0093(7) N3B 0.0244(8) 0.0221(7) 0.0283(8) 0.0048(6) 0.0038(6) 0.0039(6) C4B 0.0192(9) 0.0215(8) 0.0257(9) 0.0016(7) -0.0013(7) 0.0026(7) N4B 0.0314(10) 0.0301(8) 0.0319(9) 0.0131(7) 0.0091(7) 0.0126(7) N5B 0.0246(8) 0.0243(8) 0.0282(8) 0.0038(6) 0.0049(6) 0.0036(6) C6B 0.0236(10) 0.0201(8) 0.0284(9) 0.0015(7) 0.0014(7) 0.0004(7) C61B 0.0354(12) 0.0279(9) 0.0386(11) 0.0066(8) 0.0140(9) 0.0027(8) C1A 0.0271(10) 0.0267(9) 0.0275(9) 0.0099(7) 0.0065(8) 0.0046(7) O1A 0.0320(8) 0.0326(7) 0.0295(7) -0.0032(6) -0.0015(6) 0.0107(6) C2A 0.0330(11) 0.0364(10) 0.0298(10) 0.0095(8) 0.0055(8) 0.0035(8) Cl2A 0.0367(3) 0.0533(3) 0.0395(3) -0.0067(2) -0.0046(2) 0.0029(2) C3A 0.0510(15) 0.0591(14) 0.0296(11) 0.0143(11) -0.0035(10) 0.0059(10) C4A 0.0724(19) 0.0630(15) 0.0335(12) 0.0149(14) 0.0078(12) 0.0223(11) C5A 0.0588(16) 0.0437(12) 0.0433(13) 0.0072(11) 0.0191(12) 0.0179(10) C6A 0.0316(11) 0.0303(10) 0.0349(11) 0.0080(8) 0.0091(9) 0.0049(8) Cl6A 0.0348(3) 0.0338(3) 0.0491(3) -0.0038(2) 0.0066(2) 0.0050(2) 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' Cl Cl 0.1484 0.1585 '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 C6B N1B C2B 114.68(15) N2B C2B N3B 117.89(17) N2B C2B N1B 117.13(16) N3B C2B N1B 124.98(15) C2B N2B H2B1 117.3(15) C2B N2B H2B2 121.3(16) H2B1 N2B H2B2 121(2) C4B N3B C2B 114.98(15) N4B C4B N3B 117.81(17) N4B C4B N5B 117.79(16) N3B C4B N5B 124.40(16) C4B N4B H4B1 118.5(15) C4B N4B H4B2 119.1(14) H4B1 N4B H4B2 121(2) C6B N5B C4B 115.45(14) N1B C6B N5B 125.32(17) N1B C6B C61B 117.75(16) N5B C6B C61B 116.93(15) C6B C61B H6B1 109.5 C6B C61B H6B2 109.5 C6B C61B H6B3 109.5 C6B C61B H6BA 109.5 C6B C61B H6BB 109.5 H6BA C61B H6BB 109.5 C6B C61B H6BC 109.5 H6BA C61B H6BC 109.5 H6BB C61B H6BC 109.5 O1A C1A C2A 125.68(17) O1A C1A C6A 117.98(18) C2A C1A C6A 116.34(17) C1A O1A H1A 120.0(17) C1A C2A C3A 122.5(2) C1A C2A Cl2A 118.49(14) C3A C2A Cl2A 119.03(18) C4A C3A C2A 119.1(2) C4A C3A H3A 120.4 C2A C3A H3A 120.4 C5A C4A C3A 120.5(2) C5A C4A H4A 119.7 C3A C4A H4A 119.7 C4A C5A C6A 119.4(2) C4A C5A H5A 120.3 C6A C5A H5A 120.3 C5A C6A C1A 122.1(2) C5A C6A Cl6A 119.97(17) C1A C6A Cl6A 117.89(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1B C6B 1.330(2) N1B C2B 1.356(2) C2B N2B 1.329(2) C2B N3B 1.342(2) N2B H2B1 0.84(2) N2B H2B2 0.85(3) N3B C4B 1.338(2) C4B N4B 1.328(2) C4B N5B 1.354(2) N4B H4B1 0.83(2) N4B H4B2 0.87(3) N5B C6B 1.332(2) C6B C61B 1.488(3) C61B H6B1 0.9800 C61B H6B2 0.9800 C61B H6B3 0.9800 C61B H6BA 0.9800 C61B H6BB 0.9800 C61B H6BC 0.9800 C1A O1A 1.333(2) C1A C2A 1.382(3) C1A C6A 1.397(3) O1A H1A 0.86(3) C2A C3A 1.385(3) C2A Cl2A 1.738(2) C3A C4A 1.374(4) C3A H3A 0.9500 C4A C5A 1.372(4) C4A H4A 0.9500 C5A C6A 1.379(3) C5A H5A 0.9500 C6A Cl6A 1.736(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 N4B H4B1 O1A . 0.83(2) 2.68(2) 3.060(2) 110(2) N4B H4B1 Cl6A . 0.83(2) 3.01(2) 3.7354(17) 147(2) N2B H2B1 O1A 2_666 0.84(2) 2.53(2) 3.200(2) 139(2) N2B H2B2 N1B 2_756 0.85(3) 2.14(3) 2.987(2) 179(2) N4B H4B2 N3B 2_666 0.87(3) 2.11(3) 2.977(2) 174(2) O1A H1A N5B 1_455 0.86(3) 1.78(3) 2.6123(19) 160(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 C6B N1B C2B N2B -175.78(18) C6B N1B C2B N3B 4.6(3) N2B C2B N3B C4B 177.00(17) N1B C2B N3B C4B -3.4(3) C2B N3B C4B N4B 178.67(16) C2B N3B C4B N5B -0.9(3) N4B C4B N5B C6B -176.09(17) N3B C4B N5B C6B 3.5(3) C2B N1B C6B N5B -1.7(3) C2B N1B C6B C61B 178.69(17) C4B N5B C6B N1B -2.1(3) C4B N5B C6B C61B 177.56(16) O1A C1A C2A C3A 179.3(2) C6A C1A C2A C3A 0.3(3) O1A C1A C2A Cl2A 0.1(3) C6A C1A C2A Cl2A -178.86(14) C1A C2A C3A C4A -0.6(3) Cl2A C2A C3A C4A 178.52(19) C2A C3A C4A C5A 0.3(4) C3A C4A C5A C6A 0.3(4) C4A C5A C6A C1A -0.6(3) C4A C5A C6A Cl6A 179.68(19) O1A C1A C6A C5A -178.74(19) C2A C1A C6A C5A 0.3(3) O1A C1A C6A Cl6A 1.0(2) C2A C1A C6A Cl6A -179.97(14) _cod_database_fobs_code 2020091