#------------------------------------------------------------------------------ #$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/53/2015333.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_2015333 loop_ _publ_author_name 'Cieplik, Jerzy' 'Pluta, Janusz' 'Bryndal, Iwona' 'Lis, Tadeusz' _publ_section_title ;\ Two polymorphic forms of N-(4-chlorophenyl)-5-{[(4-chlorophenyl)amino]methyl}-6-methyl-2-\ phenylpyrimidin-4-amine ; _journal_coeditor_code SQ3007 _journal_issue 5 _journal_name_full 'Acta Crystallographica, Section C' _journal_page_first o259 _journal_page_last o261 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C24 H20 Cl2 N4' _chemical_formula_moiety 'C24 H20 Cl2 N4' _chemical_formula_sum 'C24 H20 Cl2 N4' _chemical_formula_weight 435.34 _chemical_melting_point 190 _chemical_name_common ; N-(4-chlorophenyl)-5-{[(4-chlorophenyl)amino]methyl}-6-methyl-2- phenylpyrimidin-4-amine ; _chemical_name_systematic ; N-(4-chlorophenyl)-5-{[(4-chlorophenyl)amino]methyl}-6-methyl-2- phenylpyrimidin-4-amine ; _space_group_IT_number 14 _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 SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 104.06(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 15.332(4) _cell_length_b 7.993(2) _cell_length_c 17.235(4) _cell_measurement_reflns_used 16673 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.06 _cell_measurement_theta_min 4.73 _cell_volume 2048.9(9) _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2003)' _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2003)' _computing_data_reduction CrysAlisRED _computing_molecular_graphics 'XP (Bruker, 1998)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 0 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Kuma KM4 CCD \k-geometry diffractometr' _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 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 26386 _diffrn_reflns_theta_full 28.06 _diffrn_reflns_theta_max 28.06 _diffrn_reflns_theta_min 4.73 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.336 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 904 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.49 _refine_diff_density_min -0.30 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 278 _refine_ls_number_reflns 4952 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.118 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0568 _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^)+(0.0769P)^2^+0.4721P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1346 _refine_ls_wR_factor_ref 0.1454 _reflns_number_gt 3895 _reflns_number_total 4952 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sq3007.cif _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 2015333 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 Cl Cl4 0.66123(4) 0.33111(7) 0.37837(3) 0.02978(17) Uani d . 1 Cl Cl5 0.33415(4) 0.49845(8) 0.89159(4) 0.03679(18) Uani d . 1 N N1 0.88258(12) 0.3531(2) 0.91081(10) 0.0211(4) Uani d . 1 C C2 0.86547(13) 0.2882(3) 0.83714(12) 0.0186(4) Uani d . 1 C C21 0.90082(13) 0.1179(3) 0.82712(12) 0.0189(4) Uani d . 1 C C22 0.95206(14) 0.0301(3) 0.89212(13) 0.0247(5) Uani d . 1 H H22 0.9675 0.0811 0.9434 0.030 Uiso calc R 1 C C23 0.98096(15) -0.1325(3) 0.88235(14) 0.0276(5) Uani d . 1 H H23 1.0151 -0.1922 0.9272 0.033 Uiso calc R 1 C C24 0.96003(15) -0.2073(3) 0.80745(15) 0.0270(5) Uani d . 1 H H24 0.9801 -0.3177 0.8009 0.032 Uiso calc R 1 C C25 0.90980(16) -0.1202(3) 0.74239(14) 0.0266(5) Uani d . 1 H H25 0.8957 -0.1711 0.6910 0.032 Uiso calc R 1 C C26 0.87980(15) 0.0411(3) 0.75156(13) 0.0230(5) Uani d . 1 H H26 0.8450 0.0994 0.7066 0.028 Uiso calc R 1 N N3 0.81732(12) 0.3611(2) 0.77059(10) 0.0194(4) Uani d . 1 C C4 0.78123(14) 0.5096(2) 0.77805(12) 0.0187(4) Uani d . 1 N N4 0.73384(12) 0.5890(2) 0.70989(10) 0.0215(4) Uani d . 1 H H4 0.7017(17) 0.676(3) 0.7178(15) 0.026 Uiso d . 1 C C41 0.72011(14) 0.5287(3) 0.63102(12) 0.0206(4) Uani d . 1 C C42 0.78666(15) 0.4462(3) 0.60340(13) 0.0232(5) Uani d . 1 H H42 0.8444 0.4303 0.6382 0.028 Uiso calc R 1 C C43 0.76924(15) 0.3872(3) 0.52539(13) 0.0245(5) Uani d . 1 H H43 0.8144 0.3296 0.5068 0.029 Uiso calc R 1 C C44 0.68490(15) 0.4135(3) 0.47504(12) 0.0226(5) Uani d . 1 C C45 0.61949(15) 0.5026(3) 0.50023(13) 0.0250(5) Uani d . 1 H H45 0.5629 0.5240 0.4644 0.030 Uiso calc R 1 C C46 0.63733(15) 0.5600(3) 0.57807(13) 0.0233(5) Uani d . 1 H H46 0.5927 0.6215 0.5957 0.028 Uiso calc R 1 C C5 0.78988(14) 0.5870(3) 0.85380(12) 0.0201(4) Uani d . 1 C C57 0.74856(15) 0.7570(3) 0.86288(13) 0.0239(5) Uani d . 1 H H57A 0.7455 0.7706 0.9192 0.029 Uiso calc R 1 H H57B 0.7889 0.8453 0.8512 0.029 Uiso calc R 1 N N5 0.65831(13) 0.7829(2) 0.81104(11) 0.0244(4) Uani d . 1 H H5 0.6506(17) 0.890(3) 0.7994(15) 0.029 Uiso d . 1 C C51 0.58325(15) 0.7165(3) 0.83278(12) 0.0217(4) Uani d . 1 C C52 0.58972(14) 0.5813(3) 0.88475(13) 0.0224(4) Uani d . 1 H H52 0.6470 0.5346 0.9083 0.027 Uiso calc R 1 C C53 0.51332(15) 0.5139(3) 0.90247(13) 0.0237(5) Uani d . 1 H H53 0.5183 0.4210 0.9376 0.028 Uiso calc R 1 C C54 0.42980(15) 0.5828(3) 0.86870(13) 0.0258(5) Uani d . 1 C C55 0.42173(16) 0.7183(3) 0.81736(13) 0.0270(5) Uani d . 1 H H55 0.3643 0.7655 0.7948 0.032 Uiso calc R 1 C C56 0.49781(16) 0.7847(3) 0.79899(13) 0.0261(5) Uani d . 1 H H56 0.4922 0.8769 0.7633 0.031 Uiso calc R 1 C C6 0.84411(14) 0.5028(3) 0.91826(13) 0.0209(4) Uani d . 1 C C61 0.86469(16) 0.5710(3) 1.00255(13) 0.0288(5) Uani d . 1 H H61A 0.9119 0.5032 1.0370 0.043 Uiso calc R 1 H H61B 0.8103 0.5669 1.0228 0.043 Uiso calc R 1 H H61C 0.8853 0.6871 1.0025 0.043 Uiso calc R 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 Cl4 0.0434(4) 0.0247(3) 0.0194(3) -0.0037(2) 0.0041(2) -0.0016(2) Cl5 0.0213(3) 0.0443(4) 0.0447(4) -0.0003(2) 0.0078(3) -0.0010(3) N1 0.0212(9) 0.0237(9) 0.0178(9) -0.0022(7) 0.0034(7) 0.0006(7) C2 0.0169(10) 0.0205(10) 0.0196(10) -0.0035(8) 0.0066(8) 0.0012(8) C21 0.0160(10) 0.0189(10) 0.0225(10) -0.0019(8) 0.0058(8) 0.0023(8) C22 0.0202(11) 0.0289(11) 0.0233(11) -0.0001(9) 0.0018(9) 0.0021(9) C23 0.0199(11) 0.0282(12) 0.0341(13) 0.0031(9) 0.0051(9) 0.0065(10) C24 0.0227(11) 0.0206(11) 0.0410(13) 0.0028(9) 0.0142(10) 0.0022(10) C25 0.0307(12) 0.0237(11) 0.0283(12) -0.0031(9) 0.0127(10) -0.0040(9) C26 0.0237(11) 0.0239(11) 0.0220(11) 0.0003(9) 0.0066(9) 0.0032(9) N3 0.0208(9) 0.0198(9) 0.0176(8) -0.0005(7) 0.0047(7) 0.0008(7) C4 0.0181(10) 0.0198(10) 0.0188(10) -0.0025(8) 0.0055(8) 0.0009(8) N4 0.0251(10) 0.0211(9) 0.0180(9) 0.0050(8) 0.0050(7) -0.0005(7) C41 0.0247(11) 0.0204(10) 0.0174(10) 0.0005(8) 0.0065(8) 0.0026(8) C42 0.0218(11) 0.0269(11) 0.0206(10) 0.0048(9) 0.0044(9) 0.0040(9) C43 0.0295(12) 0.0236(11) 0.0220(11) 0.0048(9) 0.0094(9) 0.0027(9) C44 0.0321(12) 0.0197(10) 0.0158(10) -0.0038(9) 0.0055(9) 0.0025(8) C45 0.0220(11) 0.0298(12) 0.0209(11) -0.0006(9) 0.0010(9) 0.0050(9) C46 0.0223(11) 0.0255(11) 0.0225(11) 0.0042(9) 0.0063(9) 0.0037(9) C5 0.0201(10) 0.0203(10) 0.0212(10) -0.0042(8) 0.0077(8) -0.0013(8) C57 0.0263(11) 0.0216(10) 0.0248(11) -0.0047(9) 0.0083(9) -0.0036(9) N5 0.0304(10) 0.0183(9) 0.0261(10) 0.0043(8) 0.0102(8) 0.0029(8) C51 0.0278(11) 0.0212(10) 0.0170(10) 0.0028(9) 0.0072(9) -0.0059(8) C52 0.0208(11) 0.0225(10) 0.0228(11) 0.0050(9) 0.0032(9) -0.0033(9) C53 0.0250(11) 0.0235(11) 0.0221(11) 0.0017(9) 0.0048(9) 0.0008(9) C54 0.0219(11) 0.0286(12) 0.0267(11) -0.0003(9) 0.0058(9) -0.0081(9) C55 0.0258(12) 0.0326(12) 0.0196(10) 0.0103(10) 0.0000(9) -0.0057(9) C56 0.0334(13) 0.0261(11) 0.0180(10) 0.0083(10) 0.0045(9) -0.0025(9) C6 0.0219(11) 0.0233(10) 0.0185(10) -0.0072(8) 0.0073(8) -0.0029(8) C61 0.0358(13) 0.0321(12) 0.0171(11) -0.0020(10) 0.0039(9) -0.0039(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' N N 0.0061 0.0033 '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 C2 N1 C6 116.32(18) N1 C2 N3 125.84(19) N1 C2 C21 118.12(18) N3 C2 C21 116.03(18) C22 C21 C26 118.9(2) C22 C21 C2 121.16(19) C26 C21 C2 119.93(19) C21 C22 C23 120.4(2) C21 C22 H22 119.8 C23 C22 H22 119.8 C24 C23 C22 120.3(2) C24 C23 H23 119.8 C22 C23 H23 119.8 C25 C24 C23 119.6(2) C25 C24 H24 120.2 C23 C24 H24 120.2 C24 C25 C26 120.6(2) C24 C25 H25 119.7 C26 C25 H25 119.7 C25 C26 C21 120.2(2) C25 C26 H26 119.9 C21 C26 H26 119.9 C4 N3 C2 117.52(18) N3 C4 N4 118.35(19) N3 C4 C5 121.96(19) N4 C4 C5 119.69(18) C4 N4 C41 126.11(18) C4 N4 H4 115.5(16) C41 N4 H4 117.5(16) C42 C41 C46 119.17(19) C42 C41 N4 122.80(19) C46 C41 N4 117.97(19) C43 C42 C41 120.5(2) C43 C42 H42 119.7 C41 C42 H42 119.7 C44 C43 C42 119.0(2) C44 C43 H43 120.5 C42 C43 H43 120.5 C45 C44 C43 121.2(2) C45 C44 Cl4 119.70(17) C43 C44 Cl4 119.07(17) C46 C45 C44 119.2(2) C46 C45 H45 120.4 C44 C45 H45 120.4 C45 C46 C41 120.7(2) C45 C46 H46 119.7 C41 C46 H46 119.7 C6 C5 C4 115.33(19) C6 C5 C57 122.22(19) C4 C5 C57 122.29(19) N5 C57 C5 114.66(17) N5 C57 H57A 108.6 C5 C57 H57A 108.6 N5 C57 H57B 108.6 C5 C57 H57B 108.6 H57A C57 H57B 107.6 C51 N5 C57 119.91(18) C51 N5 H5 110.9(17) C57 N5 H5 109.3(17) C52 C51 N5 122.18(19) C52 C51 C56 118.7(2) N5 C51 C56 119.1(2) C53 C52 C51 120.7(2) C53 C52 H52 119.6 C51 C52 H52 119.6 C54 C53 C52 119.8(2) C54 C53 H53 120.1 C52 C53 H53 120.1 C55 C54 C53 120.6(2) C55 C54 Cl5 119.83(18) C53 C54 Cl5 119.57(18) C54 C55 C56 119.7(2) C54 C55 H55 120.1 C56 C55 H55 120.1 C55 C56 C51 120.5(2) C55 C56 H56 119.8 C51 C56 H56 119.8 N1 C6 C5 122.84(19) N1 C6 C61 114.58(19) C5 C6 C61 122.6(2) 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 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl4 C44 1.746(2) Cl5 C54 1.744(2) N1 C2 1.337(3) N1 C6 1.353(3) C2 N3 1.337(3) C2 C21 1.491(3) C21 C22 1.392(3) C21 C26 1.405(3) C22 C23 1.397(3) C22 H22 0.9500 C23 C24 1.388(3) C23 H23 0.9500 C24 C25 1.384(3) C24 H24 0.9500 C25 C26 1.391(3) C25 H25 0.9500 C26 H26 0.9500 N3 C4 1.329(3) C4 N4 1.377(3) C4 C5 1.421(3) N4 C41 1.409(3) N4 H4 0.88(3) C41 C42 1.392(3) C41 C46 1.394(3) C42 C43 1.388(3) C42 H42 0.9500 C43 C44 1.387(3) C43 H43 0.9500 C44 C45 1.383(3) C45 C46 1.381(3) C45 H45 0.9500 C46 H46 0.9500 C5 C6 1.389(3) C5 C57 1.524(3) C57 N5 1.468(3) C57 H57A 0.9900 C57 H57B 0.9900 N5 C51 1.399(3) N5 H5 0.88(3) C51 C52 1.392(3) C51 C56 1.408(3) C52 C53 1.389(3) C52 H52 0.9500 C53 C54 1.386(3) C53 H53 0.9500 C54 C55 1.385(3) C55 C56 1.386(3) C55 H55 0.9500 C56 H56 0.9500 C6 C61 1.511(3) C61 H61A 0.9800 C61 H61B 0.9800 C61 H61C 0.9800 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 3.0(3) C6 N1 C2 C21 -175.53(17) N1 C2 C21 C22 -1.5(3) N3 C2 C21 C22 179.81(19) N1 C2 C21 C26 176.16(19) N3 C2 C21 C26 -2.5(3) C26 C21 C22 C23 -0.8(3) C2 C21 C22 C23 176.88(19) C21 C22 C23 C24 1.0(3) C22 C23 C24 C25 -0.4(3) C23 C24 C25 C26 -0.3(3) C24 C25 C26 C21 0.5(3) C22 C21 C26 C25 0.1(3) C2 C21 C26 C25 -177.63(19) N1 C2 N3 C4 -1.7(3) C21 C2 N3 C4 176.86(17) C2 N3 C4 N4 177.95(18) C2 N3 C4 C5 -2.4(3) N3 C4 N4 C41 -0.8(3) C5 C4 N4 C41 179.56(19) C4 N4 C41 C42 -39.4(3) C4 N4 C41 C46 143.4(2) C46 C41 C42 C43 -3.7(3) N4 C41 C42 C43 179.1(2) C41 C42 C43 C44 0.9(3) C42 C43 C44 C45 2.5(3) C42 C43 C44 Cl4 -177.11(16) C43 C44 C45 C46 -2.8(3) Cl4 C44 C45 C46 176.75(17) C44 C45 C46 C41 -0.1(3) C42 C41 C46 C45 3.4(3) N4 C41 C46 C45 -179.33(19) N3 C4 C5 C6 4.7(3) N4 C4 C5 C6 -175.66(18) N3 C4 C5 C57 -179.88(19) N4 C4 C5 C57 -0.2(3) C6 C5 C57 N5 -144.4(2) C4 C5 C57 N5 40.5(3) C5 C57 N5 C51 80.5(2) C57 N5 C51 C52 -22.9(3) C57 N5 C51 C56 159.35(19) N5 C51 C52 C53 -177.28(19) C56 C51 C52 C53 0.5(3) C51 C52 C53 C54 -0.6(3) C52 C53 C54 C55 0.0(3) C52 C53 C54 Cl5 -179.65(16) C53 C54 C55 C56 0.6(3) Cl5 C54 C55 C56 -179.74(16) C54 C55 C56 C51 -0.6(3) C52 C51 C56 C55 0.1(3) N5 C51 C56 C55 177.96(19) C2 N1 C6 C5 -0.2(3) C2 N1 C6 C61 179.62(18) C4 C5 C6 N1 -3.3(3) C57 C5 C6 N1 -178.75(19) C4 C5 C6 C61 176.85(19) C57 C5 C6 C61 1.4(3)