#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2100007.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_2100007 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 N4' _chemical_formula_sum 'C16 H16 N4' _chemical_formula_weight 264.33 _chemical_name_systematic ; 4-(3,5-dimethyl-1H-pyrazol-1-yl)-2-phenyl-pyrimidyne ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _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 4 _cell_length_a 19.499(3) _cell_length_b 4.7884(6) _cell_length_c 15.106(2) _cell_measurement_reflns_used 1009 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 22.11 _cell_measurement_theta_min 2.49 _cell_volume 1410.4(3) _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 0.999 _diffrn_measured_fraction_theta_max 0.994 _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 0.0825 _diffrn_reflns_av_sigmaI/netI 0.0986 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 9460 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 30.55 _diffrn_reflns_theta_min 2.49 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_description lath _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.140 _refine_diff_density_min -0.151 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.910 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 2221 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.910 _refine_ls_R_factor_all 0.1646 _refine_ls_R_factor_gt 0.0594 _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^)+(0.0847P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1363 _refine_ls_wR_factor_ref 0.1813 _reflns_number_gt 885 _reflns_number_total 2221 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file av5023.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M Pna2(1) _cod_original_cell_volume 1410.5(4) _cod_database_code 2100007 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, 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_type_symbol C3 0.8529(2) -0.3636(9) 0.3520(3) 0.0799(12) Uani d . 1 C C4 0.9130(2) -0.3220(9) 0.4000(3) 0.0791(11) Uani d . 1 C H4A 0.9249 -0.4103 0.4527 0.095 Uiso calc R 1 H C5 0.9513(2) -0.1272(8) 0.3556(3) 0.0727(11) Uani d . 1 C C6 0.9255(2) 0.1327(8) 0.2136(3) 0.0625(9) Uani d . 1 C C7 0.8773(2) 0.1804(8) 0.1472(3) 0.0716(11) Uani d . 1 C H7A 0.8356 0.0866 0.1455 0.086 Uiso calc R 1 H C8 0.8955(2) 0.3770(9) 0.0833(3) 0.0703(11) Uani d . 1 C C9 0.9980(2) 0.4456(8) 0.1520(3) 0.0642(10) Uani d . 1 C C10 1.0663(2) 0.5856(8) 0.1551(3) 0.0678(10) Uani d . 1 C C11 1.0834(3) 0.7937(9) 0.0965(3) 0.0792(12) Uani d . 1 C H11A 1.0513 0.8554 0.0555 0.095 Uiso calc R 1 H C12 1.1484(3) 0.9130(10) 0.0981(4) 0.0869(13) Uani d . 1 C H12A 1.1594 1.0517 0.0573 0.104 Uiso calc R 1 H C13 1.1961(2) 0.8301(10) 0.1581(4) 0.0878(14) Uani d . 1 C H13A 1.2396 0.9101 0.1586 0.105 Uiso calc R 1 H C14 1.1788(2) 0.6243(11) 0.2185(4) 0.0919(14) Uani d . 1 C H14A 1.2108 0.5674 0.2606 0.110 Uiso calc R 1 H C15 1.1147(2) 0.5032(9) 0.2169(3) 0.0799(12) Uani d . 1 C H15A 1.1039 0.3645 0.2576 0.096 Uiso calc R 1 H C31 0.7947(3) -0.5540(10) 0.3735(4) 0.1005(16) Uani d . 1 C H31A 0.7976 -0.6093 0.4344 0.121 Uiso calc R 1 H H31B 0.7970 -0.7165 0.3364 0.121 Uiso calc R 1 H H31C 0.7521 -0.4586 0.3634 0.19(3) Uiso calc R 1 H C51 1.0191(2) -0.0068(11) 0.3793(4) 0.0902(13) Uani d . 1 C H51A 1.0346 -0.0866 0.4340 0.135 Uiso calc R 1 H H51B 1.0149 0.1919 0.3858 0.135 Uiso calc R 1 H H51C 1.0516 -0.0477 0.3333 0.135 Uiso calc R 1 H C81 0.8477(2) 0.4494(12) 0.0097(3) 0.0950(15) Uani d . 1 C H81A 0.8063 0.3429 0.0156 0.143 Uiso calc R 1 H H81B 0.8691 0.4070 -0.0459 0.143 Uiso calc R 1 H H81C 0.8371 0.6450 0.0122 0.143 Uiso calc R 1 H N1 0.85223(17) -0.2084(7) 0.2793(2) 0.0753(9) Uani d . 1 N N2 0.91272(17) -0.0615(7) 0.2823(2) 0.0690(9) Uani d . 1 N N3 0.95636(17) 0.5093(7) 0.0857(2) 0.0681(9) Uani d . 1 N N4 0.98480(16) 0.2599(7) 0.2170(2) 0.0680(8) 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 C3 0.102(3) 0.059(2) 0.079(3) 0.011(2) 0.009(3) -0.010(2) C4 0.104(3) 0.064(2) 0.070(2) 0.020(2) 0.007(3) -0.001(2) C5 0.088(3) 0.071(2) 0.059(2) 0.024(2) 0.003(2) -0.006(2) C6 0.072(2) 0.061(2) 0.055(2) 0.0179(19) 0.001(2) -0.0049(18) C7 0.077(3) 0.072(3) 0.066(3) 0.0113(19) -0.003(2) -0.008(2) C8 0.078(3) 0.077(2) 0.055(2) 0.019(2) -0.003(2) -0.008(2) C9 0.080(2) 0.062(2) 0.051(2) 0.0166(19) -0.001(2) -0.0078(19) C10 0.077(3) 0.064(2) 0.063(2) 0.010(2) -0.002(2) -0.014(2) C11 0.096(3) 0.074(3) 0.068(3) 0.009(2) -0.008(2) -0.005(2) C12 0.091(3) 0.083(3) 0.086(3) -0.006(3) 0.001(3) -0.004(3) C13 0.085(3) 0.084(3) 0.095(4) -0.008(2) 0.003(3) -0.008(3) C14 0.082(3) 0.099(3) 0.095(3) 0.008(3) -0.013(3) -0.001(3) C15 0.081(3) 0.079(3) 0.081(3) 0.005(2) -0.008(2) 0.002(3) C31 0.124(4) 0.068(3) 0.109(4) 0.004(3) 0.028(3) 0.000(3) C51 0.091(3) 0.102(3) 0.077(3) 0.017(3) -0.011(3) 0.003(2) C81 0.087(3) 0.125(4) 0.073(3) 0.023(3) -0.016(2) 0.010(3) N1 0.084(2) 0.066(2) 0.076(2) 0.0082(18) 0.0038(19) -0.0034(19) N2 0.077(2) 0.0668(19) 0.0629(19) 0.0123(17) 0.0027(17) -0.0018(16) N3 0.070(2) 0.075(2) 0.0599(18) 0.0111(17) -0.0056(17) -0.0028(17) N4 0.072(2) 0.0695(19) 0.0620(19) 0.0135(16) -0.0039(18) -0.0071(19) 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 0.0000 '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 0.0000 '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 C3 C4 111.1(4) N1 C3 C31 121.0(5) C4 C3 C31 127.9(5) C5 C4 C3 107.5(5) C5 C4 H4A 126.2 C3 C4 H4A 126.2 C4 C5 N2 104.6(4) C4 C5 C51 129.2(4) N2 C5 C51 126.3(4) N4 C6 C7 123.2(4) N4 C6 N2 115.6(4) C7 C6 N2 121.2(4) C6 C7 C8 116.0(4) C6 C7 H7A 122.0 C8 C7 H7A 122.0 N3 C8 C7 121.5(4) N3 C8 C81 117.5(4) C7 C8 C81 121.0(4) N3 C9 N4 125.8(4) N3 C9 C10 117.8(4) N4 C9 C10 116.3(3) C11 C10 C15 118.3(4) C11 C10 C9 121.5(4) C15 C10 C9 120.1(4) C10 C11 C12 120.6(4) C10 C11 H11A 119.7 C12 C11 H11A 119.7 C13 C12 C11 121.0(5) C13 C12 H12A 119.5 C11 C12 H12A 119.5 C12 C13 C14 118.8(4) C12 C13 H13A 120.6 C14 C13 H13A 120.6 C15 C14 C13 120.5(5) C15 C14 H14A 119.7 C13 C14 H14A 119.7 C14 C15 C10 120.8(5) C14 C15 H15A 119.6 C10 C15 H15A 119.6 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 104.6(4) N1 N2 C5 112.3(3) N1 N2 C6 117.6(3) C5 N2 C6 130.1(4) C9 N3 C8 116.9(4) C6 N4 C9 116.6(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C3 N1 1.325(6) C3 C4 1.393(6) C3 C31 1.491(7) C4 C5 1.371(6) C4 H4A 0.9300 C5 N2 1.376(5) C5 C51 1.485(6) C6 N4 1.309(5) C6 C7 1.393(6) C6 N2 1.415(5) C7 C8 1.394(6) C7 H7A 0.9300 C8 N3 1.347(5) C8 C81 1.490(6) C9 N3 1.325(5) C9 N4 1.349(5) C9 C10 1.491(6) C10 C11 1.374(6) C10 C15 1.385(6) C11 C12 1.391(7) C11 H11A 0.9300 C12 C13 1.358(7) C12 H12A 0.9300 C13 C14 1.386(7) C13 H13A 0.9300 C14 C15 1.378(6) 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 1.374(5) 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 -177.4(3) N4 C9 C10 C15 6.4(5)