#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/57/2215767.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_2215767
loop_
_publ_author_name
'Malinowska, Katarzyna'
'Modranka, Roman'
_publ_section_title
;
 Dichlorido[(3,5-dimethyl-1H-pyrazol-1-yl)methane]copper(II)
;
_journal_coeditor_code           BH2127
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2782
_journal_page_last               m2782
_journal_paper_doi               10.1107/S1600536807048878
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu Cl2 (C11 H16 N4)]'
_chemical_formula_moiety         'C11 H16 Cl2 Cu N4'
_chemical_formula_sum            'C11 H16 Cl2 Cu N4'
_chemical_formula_weight         338.72
_chemical_melting_point          471
_chemical_name_systematic
;
Dichlorido[(3,5-dimethyl-1H-pyrazol-1-yl)methane]copper(II)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 113.580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.8120(7)
_cell_length_b                   16.7384(9)
_cell_length_c                   12.4943(6)
_cell_measurement_reflns_used    2790
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.2
_cell_measurement_theta_min      0.97
_cell_volume                     2839.1(3)
_computing_cell_refinement       'IPDS2 (Stoe & Cie, 2000)'
_computing_data_collection       'IPDS2 (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS2 (Stoe & Cie, 2000)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'PARST97 (Nardelli, 1996)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 150
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Stoe IPDSII'
_diffrn_measurement_method       ω
_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  0.4309
_diffrn_reflns_av_sigmaI/netI    0.1040
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            39701
_diffrn_reflns_theta_full        26.27
_diffrn_reflns_theta_max         26.27
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    1.902
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.370
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0301
_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/[σ²(Fo²)+(0.0335P)²+8.2559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0754
_reflns_number_gt                2619
_reflns_number_total             2790
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2127.cif
_cod_data_source_block           I
_cod_original_cell_volume        2839.0(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2215767
_cod_database_fobs_code          2215767
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'
'-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_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
Cu Cu1 0.22280(2) 0.382801(16) 0.73912(2) 0.01924(10) Uani d . 1
Cl Cl2 0.38607(4) 0.38971(4) 0.81853(6) 0.03166(15) Uani d . 1
Cl Cl3 0.15000(4) 0.50151(3) 0.70045(5) 0.02650(14) Uani d . 1
N N4 0.18202(15) 0.22504(12) 0.81646(18) 0.0246(4) Uani d . 1
N N2 0.18482(15) 0.22408(12) 0.62680(18) 0.0234(4) Uani d . 1
N N1 0.17654(15) 0.30433(12) 0.60113(18) 0.0239(4) Uani d . 1
N N3 0.17098(15) 0.30531(12) 0.83008(18) 0.0228(4) Uani d . 1
C C1 0.23608(18) 0.20058(15) 0.7477(2) 0.0243(5) Uani d . 1
H H1A 0.3023 0.2253 0.7801 0.029 Uiso calc R 1
H H1B 0.2446 0.1418 0.7524 0.029 Uiso calc R 1
C C2 0.12575(18) 0.30910(15) 0.4853(2) 0.0248(5) Uani d . 1
C C9 0.13452(18) 0.18129(16) 0.8687(2) 0.0272(5) Uani d . 1
C C4 0.14092(17) 0.17955(15) 0.5294(2) 0.0257(5) Uani d . 1
C C10 0.1347(2) 0.09174(17) 0.8698(3) 0.0378(6) Uani d . 1
H H10A 0.1020 0.0718 0.7897 0.057 Uiso calc R 1
H H10B 0.0995 0.0726 0.9166 0.057 Uiso calc R 1
H H10C 0.2028 0.0723 0.9040 0.057 Uiso calc R 1
C C7 0.11546(18) 0.31124(15) 0.8915(2) 0.0243(5) Uani d . 1
C C3 0.10333(18) 0.23234(16) 0.4379(2) 0.0265(5) Uani d . 1
H H3 0.0687 0.2192 0.3578 0.032 Uiso calc R 1
C C8 0.09196(19) 0.23490(16) 0.9179(2) 0.0285(5) Uani d . 1
H H8 0.0539 0.2225 0.9615 0.034 Uiso calc R 1
C C5 0.1358(2) 0.09069(16) 0.5300(3) 0.0354(6) Uani d . 1
H H5A 0.2010 0.0690 0.5777 0.053 Uiso calc R 1
H H5B 0.1142 0.0706 0.4499 0.053 Uiso calc R 1
H H5C 0.0887 0.0740 0.5628 0.053 Uiso calc R 1
C C11 0.0867(2) 0.39044(16) 0.9220(2) 0.0321(6) Uani d . 1
H H11A 0.1174 0.4329 0.8941 0.048 Uiso calc R 1
H H11B 0.1089 0.3945 1.0070 0.048 Uiso calc R 1
H H11C 0.0149 0.3961 0.8851 0.048 Uiso calc R 1
C C6 0.1003(2) 0.38793(16) 0.4253(2) 0.0323(6) Uani d . 1
H H6A 0.1371 0.4302 0.4795 0.048 Uiso calc R 1
H H6B 0.0295 0.3976 0.3996 0.048 Uiso calc R 1
H H6C 0.1177 0.3878 0.3574 0.048 Uiso calc R 1
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 N3 89.30(8)
N1 Cu1 Cl2 110.26(7)
N3 Cu1 Cl2 111.42(6)
N1 Cu1 Cl3 114.82(6)
N3 Cu1 Cl3 115.28(6)
Cl2 Cu1 Cl3 113.46(3)
C9 N4 N3 111.1(2)
C9 N4 C1 130.7(2)
N3 N4 C1 118.2(2)
C4 N2 N1 111.3(2)
C4 N2 C1 130.7(2)
N1 N2 C1 118.00(19)
C2 N1 N2 105.6(2)
C2 N1 Cu1 136.29(17)
N2 N1 Cu1 117.39(15)
C7 N3 N4 106.0(2)
C7 N3 Cu1 136.09(17)
N4 N3 Cu1 117.25(15)
N2 C1 N4 111.01(19)
N2 C1 H1A 109.4
N4 C1 H1A 109.4
N2 C1 H1B 109.4
N4 C1 H1B 109.4
H1A C1 H1B 108.0
N1 C2 C3 109.8(2)
N1 C2 C6 121.1(2)
C3 C2 C6 129.2(2)
N4 C9 C8 106.4(2)
N4 C9 C10 123.2(2)
C8 C9 C10 130.4(2)
N2 C4 C3 106.5(2)
N2 C4 C5 123.6(2)
C3 C4 C5 129.9(2)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N3 C7 C8 109.7(2)
N3 C7 C11 121.3(2)
C8 C7 C11 129.0(2)
C4 C3 C2 106.9(2)
C4 C3 H3 126.6
C2 C3 H3 126.6
C9 C8 C7 106.8(2)
C9 C8 H8 126.6
C7 C8 H8 126.6
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C7 C11 H11A 109.5
C7 C11 H11B 109.5
H11A C11 H11B 109.5
C7 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C2 C6 H6A 109.5
C2 C6 H6B 109.5
H6A C6 H6B 109.5
C2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu1 N1 2.055(2)
Cu1 N3 2.064(2)
Cu1 Cl2 2.2195(9)
Cu1 Cl3 2.2197(7)
N4 C9 1.351(3)
N4 N3 1.372(3)
N4 C1 1.448(3)
N2 C4 1.352(3)
N2 N1 1.375(3)
N2 C1 1.448(3)
N1 C2 1.340(3)
N3 C7 1.334(3)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.398(4)
C2 C6 1.490(4)
C9 C8 1.375(4)
C9 C10 1.499(4)
C4 C3 1.374(4)
C4 C5 1.490(4)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C7 C8 1.398(4)
C7 C11 1.488(4)
C3 H3 0.9500
C8 H8 0.9500
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
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
_geom_hbond_publ_flag
C1 H1B Cl3 4_546 0.99 2.75 3.674(2) 155 yes
C6 H6C Cl3 6_565 0.98 2.87 3.676(3) 140 yes
C11 H11B Cl3 6_566 0.98 2.84 3.692(3) 146 yes
C11 H11C Cl3 2_556 0.98 2.85 3.714(2) 147 yes
