#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/00/2100009.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_2100009 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) emerald green form ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _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 8 _cell_length_a 11.6899(6) _cell_length_b 14.9843(8) _cell_length_c 19.2115(9) _cell_measurement_reflns_used 4601 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 30.45 _cell_measurement_theta_min 2.45 _cell_volume 3365.2(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 0.892 _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 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 17334 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 32.36 _diffrn_reflns_theta_min 2.12 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.619 _exptl_absorpt_correction_T_max 0.86 _exptl_absorpt_correction_T_min 0.6571 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Bruker)' _exptl_crystal_colour 'clear emerald green' _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'elongated prism' _exptl_crystal_F_000 1624 _exptl_crystal_size_max 0.328 _exptl_crystal_size_mid 0.102 _exptl_crystal_size_min 0.091 _refine_diff_density_max 0.494 _refine_diff_density_min -0.435 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.862 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 5379 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.862 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0323 _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^)+(0.0530P)^2^+2.2199P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0834 _refine_ls_wR_factor_ref 0.0984 _reflns_number_gt 3611 _reflns_number_total 5379 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file av5023.cif _[local]_cod_data_source_block 2eg _[local]_cod_cif_authors_sg_H-M Pbca _cod_database_code 2100009 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' 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 0.751430(18) 0.839560(17) 0.548815(12) 0.03193(8) Uani d . 1 . . Cu Cl1 0.71694(4) 0.74685(4) 0.63721(3) 0.04276(13) Uani d . 1 . . Cl Cl2 0.93311(4) 0.86988(5) 0.56060(3) 0.05205(15) Uani d . 1 . . Cl C3 0.79496(17) 0.81698(14) 0.38867(10) 0.0364(4) Uani d . 1 . . C C4 0.72127(18) 0.80284(16) 0.33277(11) 0.0403(5) Uani d . 1 . . C H4A 0.7428 0.7869 0.2879 0.048 Uiso calc R 1 . . H C5 0.61204(17) 0.81652(13) 0.35544(10) 0.0337(4) Uani d . 1 . . C C6 0.54197(15) 0.86338(12) 0.47575(9) 0.0281(3) Uani d . 1 . . C C7 0.42510(15) 0.86907(13) 0.46564(10) 0.0323(4) Uani d . 1 . . C H7A 0.3915 0.8540 0.4233 0.039 Uiso calc R 1 . . H C8 0.36002(16) 0.89850(13) 0.52199(10) 0.0330(4) Uani d . 1 . . C C9 0.52140(15) 0.91422(12) 0.58829(9) 0.0297(4) Uani d . 1 . . C C10 0.57579(16) 0.94086(13) 0.65468(9) 0.0321(4) Uani d . 1 . . C C11 0.5195(2) 0.92555(15) 0.71717(11) 0.0450(5) Uani d . 1 . . C H11A 0.4460 0.9019 0.7172 0.054 Uiso calc R 1 . . H C12 0.5732(3) 0.94568(18) 0.77950(12) 0.0581(6) Uani d . 1 . . C H12A 0.5362 0.9342 0.8214 0.070 Uiso calc R 1 . . H C13 0.6811(2) 0.98264(18) 0.77971(12) 0.0563(6) Uani d . 1 . . C H13A 0.7169 0.9952 0.8218 0.068 Uiso calc R 1 . . H C14 0.7361(2) 1.00108(16) 0.71794(13) 0.0478(5) Uani d . 1 . . C H14A 0.8078 1.0280 0.7182 0.057 Uiso calc R 1 . . H C15 0.68394(17) 0.97928(14) 0.65567(10) 0.0368(4) Uani d . 1 . . C H15A 0.7217 0.9905 0.6139 0.044 Uiso calc R 1 . . H C31 0.92214(18) 0.81407(19) 0.38827(12) 0.0521(6) Uani d . 1 . . C H31A 0.9516 0.8724 0.3779 0.078 Uiso calc R 1 . . H H31B 0.9477 0.7726 0.3535 0.078 Uiso calc R 1 . . H H31C 0.9492 0.7954 0.4331 0.078 Uiso calc R 1 . . H C51 0.50499(19) 0.81183(17) 0.31405(10) 0.0452(5) Uani d . 1 . . C H51A 0.5229 0.7955 0.2670 0.068 Uiso calc R 1 . . H H51B 0.4680 0.8690 0.3145 0.068 Uiso calc R 1 . . H H51C 0.4549 0.7679 0.3339 0.068 Uiso calc R 1 . . H C81 0.23295(17) 0.90503(17) 0.51881(13) 0.0442(5) Uani d . 1 . . C H81A 0.2001 0.8721 0.5567 0.066 Uiso calc R 1 . . H H81B 0.2064 0.8807 0.4755 0.066 Uiso calc R 1 . . H H81C 0.2105 0.9665 0.5222 0.066 Uiso calc R 1 . . H N1 0.73495(12) 0.83749(11) 0.44553(8) 0.0316(3) Uani d . 1 . . N N2 0.62136(13) 0.83753(10) 0.42500(8) 0.0295(3) Uani d . 1 . . N N3 0.40850(13) 0.92337(11) 0.58266(9) 0.0348(4) Uani d . 1 . . N N4 0.58950(12) 0.88237(11) 0.53781(8) 0.0282(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 0.02606(11) 0.04428(15) 0.02545(13) 0.00235(9) -0.00037(8) 0.00186(9) Cl1 0.0403(2) 0.0539(3) 0.0341(3) 0.0093(2) 0.00545(19) 0.0107(2) Cl2 0.0298(2) 0.0792(4) 0.0471(3) -0.0078(3) -0.0035(2) -0.0021(3) C3 0.0355(9) 0.0458(11) 0.0278(9) 0.0054(8) 0.0088(8) 0.0050(8) C4 0.0449(11) 0.0511(12) 0.0248(9) 0.0053(9) 0.0065(8) 0.0002(9) C5 0.0386(10) 0.0389(10) 0.0236(9) -0.0004(8) -0.0004(7) 0.0000(7) C6 0.0290(8) 0.0304(8) 0.0247(8) 0.0004(7) 0.0013(7) 0.0022(7) C7 0.0286(8) 0.0389(10) 0.0294(9) -0.0002(7) -0.0020(7) -0.0002(8) C8 0.0284(8) 0.0382(10) 0.0323(10) 0.0006(7) 0.0004(7) 0.0015(8) C9 0.0305(8) 0.0324(9) 0.0260(8) 0.0020(7) 0.0029(7) -0.0017(7) C10 0.0358(9) 0.0360(9) 0.0244(9) 0.0053(7) 0.0011(7) -0.0023(7) C11 0.0493(12) 0.0528(13) 0.0330(11) -0.0025(10) 0.0087(9) -0.0046(9) C12 0.0818(18) 0.0668(16) 0.0257(10) -0.0018(14) 0.0073(11) -0.0009(11) C13 0.0766(17) 0.0598(15) 0.0325(11) 0.0008(13) -0.0136(11) -0.0066(10) C14 0.0492(13) 0.0523(13) 0.0419(12) -0.0002(10) -0.0119(10) -0.0059(10) C15 0.0368(9) 0.0426(10) 0.0311(10) 0.0035(8) -0.0003(8) -0.0032(8) C31 0.0365(11) 0.0822(17) 0.0378(12) 0.0125(11) 0.0109(9) 0.0074(12) C51 0.0436(11) 0.0653(14) 0.0269(10) -0.0024(10) -0.0045(8) -0.0068(10) C81 0.0298(10) 0.0566(14) 0.0461(13) 0.0012(9) 0.0020(8) -0.0020(10) N1 0.0261(7) 0.0437(9) 0.0250(8) 0.0029(6) 0.0019(5) 0.0011(6) N2 0.0257(7) 0.0402(8) 0.0225(7) 0.0021(6) 0.0012(6) -0.0015(6) N3 0.0302(8) 0.0418(9) 0.0325(8) 0.0028(6) 0.0025(6) -0.0025(7) N4 0.0268(7) 0.0344(8) 0.0233(7) 0.0016(6) -0.0003(5) -0.0011(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 . 1.9938(16) ? Cu1 N4 . 2.0098(15) ? Cu1 Cl2 . 2.1836(6) ? Cu1 Cl1 . 2.2307(6) ? C3 N1 . 1.334(2) ? C3 C4 . 1.393(3) ? C3 C31 . 1.487(3) ? C4 C5 . 1.365(3) ? C4 H4A . 0.9300 ? C5 N2 . 1.377(2) ? C5 C51 . 1.484(3) ? C6 N4 . 1.346(2) ? C6 C7 . 1.383(2) ? C6 N2 . 1.401(2) ? C7 C8 . 1.395(3) ? C7 H7A . 0.9300 ? C8 N3 . 1.349(3) ? C8 C81 . 1.490(3) ? C9 N3 . 1.331(2) ? C9 N4 . 1.342(2) ? C9 C10 . 1.480(3) ? C10 C15 . 1.389(3) ? C10 C11 . 1.388(3) ? C11 C12 . 1.385(3) ? C11 H11A . 0.9300 ? C12 C13 . 1.377(4) ? C12 H12A . 0.9300 ? C13 C14 . 1.378(3) ? C13 H13A . 0.9300 ? C14 C15 . 1.382(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 . 1.385(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 79.01(6) N1 Cu1 Cl2 101.56(5) N4 Cu1 Cl2 149.38(5) N1 Cu1 Cl1 136.93(5) N4 Cu1 Cl1 96.23(5) Cl2 Cu1 Cl1 103.09(2) N1 C3 C4 109.95(17) N1 C3 C31 122.45(19) C4 C3 C31 127.57(18) C5 C4 C3 108.05(18) C5 C4 H4A 126.0 C3 C4 H4A 126.0 C4 C5 N2 105.66(17) C4 C5 C51 127.65(18) N2 C5 C51 126.68(18) N4 C6 C7 121.29(16) N4 C6 N2 113.68(15) C7 C6 N2 125.02(17) C6 C7 C8 116.71(17) C6 C7 H7A 121.6 C8 C7 H7A 121.6 N3 C8 C7 121.94(17) N3 C8 C81 115.87(18) C7 C8 C81 122.19(19) N3 C9 N4 124.47(17) N3 C9 C10 117.91(16) N4 C9 C10 117.62(16) C15 C10 C11 119.20(19) C15 C10 C9 120.97(17) C11 C10 C9 119.82(18) C12 C11 C10 119.8(2) C12 C11 H11A 120.1 C10 C11 H11A 120.1 C13 C12 C11 120.3(2) C13 C12 H12A 119.8 C11 C12 H12A 119.8 C12 C13 C14 120.4(2) C12 C13 H13A 119.8 C14 C13 H13A 119.8 C13 C14 C15 119.4(2) C13 C14 H14A 120.3 C15 C14 H14A 120.3 C14 C15 C10 120.8(2) 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 105.72(16) C3 N1 Cu1 140.14(14) N2 N1 Cu1 112.09(11) C5 N2 N1 110.61(14) C5 N2 C6 133.33(16) N1 N2 C6 115.91(14) C9 N3 C8 117.28(16) C9 N4 C6 118.05(15) C9 N4 Cu1 126.59(12) C6 N4 Cu1 114.49(12) 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 -1.5(2) N4 C9 C10 C15 35.2(3) _cod_database_fobs_code 2100009