#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/00/2100010.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_2100010 loop_ _publ_author_name 'Peresypkina, Eugenia V.' 'Bushuev, Mark B.' 'Virovets, Alexander V.' 'Krivopalov, Victor P.' 'Lavrenova, Ludmila G.' 'Larionov, Stanislav V.' _publ_section_title ;Three differently coloured concomitant polymorphs: synthesis, structure and packing analysis of (4-(3',5'-dimethyl-1H-pyrazol-1'-yl)-6-methyl-2-phenylpyrimidine)dichlorocopper(II) ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 164 _journal_page_last 173 _journal_volume 61 _journal_year 2005 _chemical_formula_moiety 'C16 H16 Cl2 Cu N4' _chemical_formula_sum 'C16 H16 Cl2 Cu N4' _chemical_formula_weight 398.77 _chemical_name_systematic ; (4-(3,5-dimethyl-1H-pyrazol-1-yl)-2-phenyl-pyrimidyne)dichlorocopper(II) orange form ; _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 SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 108.5440(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.7652(6) _cell_length_b 18.7631(10) _cell_length_c 9.8115(4) _cell_measurement_temperature 293(2) _cell_volume 1704.38(16) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL, TOPOS 4.0 Standard' _computing_publication_material 'local programs' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 25 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Bruker-Nonius X8Apex CCD area-detector' _diffrn_measurement_method \p-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 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 12988 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.57 _diffrn_reflns_theta_min 2.17 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.598 _exptl_absorpt_correction_T_max 0.8200 _exptl_absorpt_correction_T_min 0.7206 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Bruker)' _exptl_crystal_colour 'clear orange' _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 812 _exptl_crystal_size_max 0.308 _exptl_crystal_size_mid 0.172 _exptl_crystal_size_min 0.122 _refine_diff_density_max 0.377 _refine_diff_density_min -0.283 _refine_ls_extinction_coef 0.0021(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3915 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.097 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0290 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.2601P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0838 _refine_ls_wR_factor_ref 0.0877 _reflns_number_gt 3240 _reflns_number_total 3915 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file av5023.cif _[local]_cod_data_source_block 2o _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2100010 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_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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cu1 0.35577(2) 0.953703(11) 0.63529(2) 0.03640(10) Uani d . 1 . . Cu Cl1 0.26509(5) 0.85393(2) 0.69352(5) 0.04572(14) Uani d . 1 . . Cl Cl2 0.26863(6) 0.95797(3) 0.39918(5) 0.04932(14) Uani d . 1 . . Cl C3 0.2445(2) 1.10742(10) 0.6439(2) 0.0429(4) Uani d . 1 . . C C4 0.2987(2) 1.16774(11) 0.7277(2) 0.0471(5) Uani d . 1 . . C H4A 0.2528 1.2117 0.7207 0.056 Uiso calc R 1 . . H C5 0.4302(2) 1.15061(9) 0.8209(2) 0.0406(4) Uani d . 1 . . C C6 0.56506(19) 1.03183(9) 0.85684(19) 0.0342(4) Uani d . 1 . . C C7 0.68466(19) 1.04774(11) 0.9723(2) 0.0423(5) Uani d . 1 . . C H7A 0.6963 1.0924 1.0157 0.051 Uiso calc R 1 . . H C8 0.7868(2) 0.99460(12) 1.0210(2) 0.0443(5) Uani d . 1 . . C C9 0.65500(18) 0.91947(10) 0.84397(19) 0.0375(4) Uani d . 1 . . C C10 0.6418(2) 0.84987(10) 0.7705(2) 0.0410(4) Uani d . 1 . . C C11 0.6852(3) 0.78836(12) 0.8515(3) 0.0578(6) Uani d . 1 . . C H11A 0.7306 0.7917 0.9502 0.069 Uiso calc R 1 . . H C12 0.6613(3) 0.72257(13) 0.7865(4) 0.0756(8) Uani d . 1 . . C H12A 0.6879 0.6814 0.8414 0.091 Uiso calc R 1 . . H C13 0.5983(3) 0.71794(13) 0.6405(4) 0.0763(8) Uani d . 1 . . C H13A 0.5808 0.6733 0.5970 0.092 Uiso calc R 1 . . H C14 0.5605(3) 0.77812(13) 0.5572(3) 0.0624(6) Uani d . 1 . . C H14A 0.5204 0.7743 0.4579 0.075 Uiso calc R 1 . . H C15 0.5823(2) 0.84446(11) 0.6220(2) 0.0477(5) Uani d . 1 . . C H15A 0.5573 0.8854 0.5662 0.057 Uiso calc R 1 . . H C31 0.1050(2) 1.09956(12) 0.5253(3) 0.0616(6) Uani d . 1 . . C H31A 0.1136 1.1204 0.4391 0.092 Uiso calc R 1 . . H H31B 0.0298 1.1233 0.5513 0.092 Uiso calc R 1 . . H H31C 0.0818 1.0499 0.5093 0.092 Uiso calc R 1 . . H C51 0.5336(2) 1.19784(11) 0.9267(2) 0.0569(6) Uani d . 1 . . C H51A 0.4912 1.2441 0.9249 0.085 Uiso calc R 1 . . H H51B 0.6209 1.2020 0.9021 0.085 Uiso calc R 1 . . H H51C 0.5554 1.1778 1.0212 0.085 Uiso calc R 1 . . H C81 0.9208(2) 1.00655(15) 1.1464(2) 0.0600(6) Uani d . 1 . . C H81A 0.9661 0.9616 1.1793 0.090 Uiso calc R 1 . . H H81B 0.8956 1.0293 1.2227 0.090 Uiso calc R 1 . . H H81C 0.9863 1.0364 1.1172 0.090 Uiso calc R 1 . . H N1 0.33813(17) 1.05425(8) 0.68426(18) 0.0390(4) Uani d . 1 . . N N2 0.45345(15) 1.07999(8) 0.79458(15) 0.0347(3) Uani d . 1 . . N N3 0.77311(17) 0.93061(10) 0.95595(18) 0.0444(4) Uani d . 1 . . N N4 0.54687(15) 0.96688(8) 0.79507(16) 0.0335(3) Uani d . 1 . . N 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 Cu1 0.03786(15) 0.02895(14) 0.03432(15) -0.00187(8) 0.00005(10) 0.00082(8) Cl1 0.0478(3) 0.0376(2) 0.0470(3) -0.00841(19) 0.0084(2) 0.00478(19) Cl2 0.0595(3) 0.0456(3) 0.0339(3) -0.0068(2) 0.0021(2) 0.00339(19) C3 0.0396(10) 0.0349(9) 0.0474(11) 0.0041(8) 0.0040(8) 0.0022(8) C4 0.0518(11) 0.0323(9) 0.0528(12) 0.0057(8) 0.0105(9) 0.0013(8) C5 0.0471(10) 0.0319(9) 0.0418(10) -0.0038(8) 0.0129(8) -0.0032(7) C6 0.0314(8) 0.0376(9) 0.0326(9) -0.0026(7) 0.0088(7) 0.0018(7) C7 0.0336(9) 0.0495(12) 0.0394(10) -0.0036(8) 0.0054(8) -0.0087(8) C8 0.0307(9) 0.0649(13) 0.0346(10) -0.0019(8) 0.0068(7) 0.0007(9) C9 0.0318(9) 0.0424(10) 0.0366(9) 0.0008(7) 0.0088(7) 0.0076(8) C10 0.0327(9) 0.0387(10) 0.0514(11) 0.0053(7) 0.0132(8) 0.0055(8) C11 0.0554(12) 0.0485(12) 0.0692(15) 0.0161(10) 0.0196(11) 0.0142(11) C12 0.0837(19) 0.0426(13) 0.107(2) 0.0169(12) 0.0389(17) 0.0165(14) C13 0.0863(19) 0.0384(13) 0.119(3) -0.0027(12) 0.0530(19) -0.0159(14) C14 0.0599(14) 0.0604(15) 0.0714(16) -0.0038(11) 0.0275(12) -0.0180(12) C15 0.0475(11) 0.0422(11) 0.0539(12) 0.0044(9) 0.0170(9) -0.0004(9) C31 0.0465(12) 0.0489(12) 0.0682(15) 0.0092(10) -0.0116(11) -0.0003(11) C51 0.0603(14) 0.0404(11) 0.0605(14) -0.0071(10) 0.0058(11) -0.0121(10) C81 0.0346(11) 0.0918(18) 0.0442(12) 0.0022(11) -0.0010(9) -0.0068(12) N1 0.0359(8) 0.0322(8) 0.0392(8) 0.0001(6) -0.0017(6) -0.0030(6) N2 0.0315(7) 0.0316(7) 0.0346(8) -0.0024(6) 0.0015(6) -0.0036(6) N3 0.0322(8) 0.0555(10) 0.0412(9) 0.0061(7) 0.0058(7) 0.0051(8) N4 0.0297(7) 0.0343(7) 0.0332(8) -0.0005(6) 0.0055(6) 0.0024(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 N1 . 1.9679(15) ? Cu1 N4 . 2.0348(14) ? Cu1 Cl2 . 2.2008(5) ? Cu1 Cl1 . 2.2219(5) ? C3 N1 . 1.326(2) ? C3 C4 . 1.400(3) ? C3 C31 . 1.491(3) ? C4 C5 . 1.357(3) ? C4 H4A . 0.9300 ? C5 N2 . 1.383(2) ? C5 C51 . 1.488(3) ? C6 N4 . 1.347(2) ? C6 C7 . 1.376(2) ? C6 N2 . 1.398(2) ? C7 C8 . 1.384(3) ? C7 H7A . 0.9300 ? C8 N3 . 1.346(3) ? C8 C81 . 1.500(3) ? C9 N3 . 1.332(2) ? C9 N4 . 1.347(2) ? C9 C10 . 1.477(3) ? C10 C11 . 1.389(3) ? C10 C15 . 1.391(3) ? C11 C12 . 1.375(4) ? C11 H11A . 0.9300 ? C12 C13 . 1.371(4) ? C12 H12A . 0.9300 ? C13 C14 . 1.374(4) ? C13 H13A . 0.9300 ? C14 C15 . 1.383(3) ? C14 H14A . 0.9300 ? C15 H15A . 0.9300 ? C31 H31A . 0.9600 ? C31 H31B . 0.9600 ? C31 H31C . 0.9600 ? C51 H51A . 0.9600 ? C51 H51B . 0.9600 ? C51 H51C . 0.9600 ? C81 H81A . 0.9600 ? C81 H81B . 0.9600 ? C81 H81C . 0.9600 ? N1 N2 . 1.378(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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 N1 Cu1 N4 79.95(6) N1 Cu1 Cl2 100.81(5) N4 Cu1 Cl2 139.41(5) N1 Cu1 Cl1 132.22(5) N4 Cu1 Cl1 104.31(4) Cl2 Cu1 Cl1 104.42(2) N1 C3 C4 109.70(17) N1 C3 C31 122.06(18) C4 C3 C31 128.24(18) C5 C4 C3 107.71(17) C5 C4 H4A 126.1 C3 C4 H4A 126.1 C4 C5 N2 106.10(16) C4 C5 C51 127.99(18) N2 C5 C51 125.85(18) N4 C6 C7 121.49(17) N4 C6 N2 114.53(15) C7 C6 N2 123.99(17) C6 C7 C8 117.25(18) C6 C7 H7A 121.4 C8 C7 H7A 121.4 N3 C8 C7 121.79(17) N3 C8 C81 116.82(19) C7 C8 C81 121.4(2) N3 C9 N4 124.41(18) N3 C9 C10 117.35(17) N4 C9 C10 118.24(16) C11 C10 C15 119.2(2) C11 C10 C9 119.50(19) C15 C10 C9 121.23(17) C12 C11 C10 120.4(2) C12 C11 H11A 119.8 C10 C11 H11A 119.8 C13 C12 C11 119.7(2) C13 C12 H12A 120.2 C11 C12 H12A 120.2 C12 C13 C14 121.0(2) C12 C13 H13A 119.5 C14 C13 H13A 119.5 C13 C14 C15 119.6(2) C13 C14 H14A 120.2 C15 C14 H14A 120.2 C14 C15 C10 119.9(2) C14 C15 H15A 120.0 C10 C15 H15A 120.0 C3 C31 H31A 109.5 C3 C31 H31B 109.5 H31A C31 H31B 109.5 C3 C31 H31C 109.5 H31A C31 H31C 109.5 H31B C31 H31C 109.5 C5 C51 H51A 109.5 C5 C51 H51B 109.5 H51A C51 H51B 109.5 C5 C51 H51C 109.5 H51A C51 H51C 109.5 H51B C51 H51C 109.5 C8 C81 H81A 109.5 C8 C81 H81B 109.5 H81A C81 H81B 109.5 C8 C81 H81C 109.5 H81A C81 H81C 109.5 H81B C81 H81C 109.5 C3 N1 N2 106.54(14) C3 N1 Cu1 138.95(13) N2 N1 Cu1 114.50(11) N1 N2 C5 109.94(14) N1 N2 C6 116.47(14) C5 N2 C6 133.58(15) C9 N3 C8 117.41(17) C9 N4 C6 117.44(15) C9 N4 Cu1 128.11(13) C6 N4 Cu1 114.45(11) 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 N1 N2 C6 N4 2.8(2) N4 C9 C10 C15 38.6(3)