#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/34/2013418.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_2013418
loop_
_publ_author_name
'Sbai, F.'
'Regragui, R.'
'Essassi, E., M.'
'Kenz, A.'
'Pierrot, M.'
_publ_section_title
;
 Complexation du 2-[(5-méthylpyrazolyl)méthyle]benzimidazole par
 les chlorures de cuivre et de cadmium
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m334
_journal_page_last               m336
_journal_paper_doi               10.1107/S0108270103013945
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '[Cd2 Cl4 (C12 H12 N4)2]'
_chemical_formula_moiety         'C24 H24 Cd2 Cl4 N8'
_chemical_formula_sum            'C24 H24 Cd2 Cl4 N8'
_chemical_formula_weight         791.13
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                92.8610(10)
_cell_angle_beta                 112.0140(10)
_cell_angle_gamma                105.4930(10)
_cell_formula_units_Z            1
_cell_length_a                   7.8306(2)
_cell_length_b                   9.7979(3)
_cell_length_c                   10.1976(4)
_cell_measurement_reflns_used    10163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.
_cell_measurement_theta_min      2
_cell_volume                     689.07(4)
_computing_data_collection       'KappaCCD (Nonius, 1998) '
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'φ scan'
_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  0.027
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10163
_diffrn_reflns_theta_full        26.46
_diffrn_reflns_theta_max         26.
_diffrn_reflns_theta_min         2.82
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.962
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.473
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0215
_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)+(0.0041P)²+0.8027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0495
_refine_ls_wR_factor_ref         0.0511
_reflns_number_gt                2474
_reflns_number_total             2614
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            dn1026.cif
_cod_data_source_block           II
_cod_database_code               2013418
_cod_database_fobs_code          2013418
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cd1 0.27325(3) 0.336088(19) 0.47595(2) 0.02774(7) Uani d . 1 . . Cd
Cl3 -0.03141(10) 0.33503(8) 0.28348(8) 0.04374(17) Uani d . 1 . . Cl
Cl2 0.56172(10) 0.38913(7) 0.40148(8) 0.03556(15) Uani d . 1 . . Cl
N1 0.2474(3) 0.0970(2) 0.4594(2) 0.0284(4) Uani d . 1 . . N
N8 0.2560(3) -0.1181(2) 0.5112(2) 0.0337(5) Uani d . 1 . . N
H8 0.2621 -0.1874 0.5596 0.040 Uiso calc R 1 . . H
N12 0.2414(3) 0.2942(2) 0.6848(2) 0.0330(5) Uani d . 1 . . N
N13 0.2332(4) 0.3980(2) 0.7738(3) 0.0366(5) Uani d . 1 . . N
H13 0.2133 0.4770 0.7494 0.044 Uiso calc R 1 . . H
C2 0.2329(3) 0.0118(3) 0.3394(3) 0.0287(5) Uani d . 1 . . C
C3 0.2122(4) 0.0431(3) 0.2043(3) 0.0369(6) Uani d . 1 . . C
H3 0.2076 0.1332 0.1815 0.044 Uiso calc R 1 . . H
C4 0.1985(4) -0.0644(3) 0.1050(3) 0.0413(6) Uani d . 1 . . C
H4 0.1832 -0.0467 0.0131 0.050 Uiso calc R 1 . . H
C5 0.2072(4) -0.1989(3) 0.1391(3) 0.0432(7) Uani d . 1 . . C
H5 0.1989 -0.2684 0.0695 0.052 Uiso calc R 1 . . H
C6 0.2275(4) -0.2320(3) 0.2722(3) 0.0413(7) Uani d . 1 . . C
H6 0.2332 -0.3220 0.2947 0.050 Uiso calc R 1 . . H
C7 0.2392(4) -0.1239(3) 0.3715(3) 0.0310(5) Uani d . 1 . . C
C9 0.2613(3) 0.0142(3) 0.5594(3) 0.0278(5) Uani d . 1 . . C
C10 0.2836(4) 0.0500(3) 0.7095(3) 0.0332(6) Uani d . 1 . . C
H10A 0.4079 0.0420 0.7720 0.040 Uiso calc R 1 . . H
H10B 0.1851 -0.0243 0.7238 0.040 Uiso calc R 1 . . H
C11 0.2728(3) 0.1912(3) 0.7619(3) 0.0284(5) Uani d . 1 . . C
C14 0.2595(4) 0.3633(3) 0.9036(3) 0.0363(6) Uani d . 1 . . C
C15 0.2882(4) 0.2321(3) 0.8999(3) 0.0366(6) Uani d . 1 . . C
H15 0.3132 0.1799 0.9749 0.044 Uiso calc R 1 . . H
C16 0.2523(5) 0.4585(4) 1.0182(3) 0.0481(7) Uani d . 1 . . C
H16A 0.3503 0.5496 1.0398 0.072 Uiso calc R 1 . . H
H16B 0.2748 0.4149 1.1029 0.072 Uiso calc R 1 . . H
H16C 0.1272 0.4726 0.9861 0.072 Uiso calc R 1 . . H
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'
Cd Cd -0.8075 1.2024 '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'
N N 0.0061 0.0033 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N12 Cd1 N1 . 80.44(8) y
N12 Cd1 Cl3 . 112.74(6) y
N1 Cd1 Cl3 . 102.18(6) y
N12 Cd1 Cl2 . 133.64(6) y
N1 Cd1 Cl2 . 91.02(5) y
Cl3 Cd1 Cl2 . 113.61(3) y
N12 Cd1 Cl2 2_666 86.40(6) y
N1 Cd1 Cl2 2_666 154.17(6) y
Cl3 Cd1 Cl2 2_666 103.40(2) y
Cl2 Cd1 Cl2 2_666 82.09(2) y
Cd1 Cl2 Cd1 2_666 97.91(2) y
C9 N1 C2 . 105.6(2) ?
C9 N1 Cd1 . 129.45(18) ?
C2 N1 Cd1 . 124.67(16) ?
C9 N8 C7 . 108.6(2) ?
C9 N8 H8 . 125.7 ?
C7 N8 H8 . 125.7 ?
C11 N12 N13 . 105.2(2) ?
C11 N12 Cd1 . 131.02(18) ?
N13 N12 Cd1 . 121.92(15) ?
C14 N13 N12 . 112.3(2) ?
C14 N13 H13 . 123.8 ?
N12 N13 H13 . 123.8 ?
C3 C2 C7 . 120.5(2) ?
C3 C2 N1 . 130.2(2) ?
C7 C2 N1 . 109.3(2) ?
C4 C3 C2 . 117.4(3) ?
C4 C3 H3 . 121.3 ?
C2 C3 H3 . 121.3 ?
C3 C4 C5 . 121.5(3) ?
C3 C4 H4 . 119.3 ?
C5 C4 H4 . 119.3 ?
C6 C5 C4 . 122.0(3) ?
C6 C5 H5 . 119.0 ?
C4 C5 H5 . 119.0 ?
C5 C6 C7 . 116.4(3) ?
C5 C6 H6 . 121.8 ?
C7 C6 H6 . 121.8 ?
N8 C7 C6 . 132.8(2) ?
N8 C7 C2 . 104.9(2) ?
C6 C7 C2 . 122.3(3) ?
N1 C9 N8 . 111.6(2) ?
N1 C9 C10 . 128.9(2) ?
N8 C9 C10 . 119.5(2) ?
C9 C10 C11 . 120.6(2) ?
C9 C10 H10A . 107.2 ?
C11 C10 H10A . 107.2 ?
C9 C10 H10B . 107.2 ?
C11 C10 H10B . 107.2 ?
H10A C10 H10B . 106.8 ?
N12 C11 C15 . 109.8(2) ?
N12 C11 C10 . 125.9(2) ?
C15 C11 C10 . 124.3(2) ?
N13 C14 C15 . 105.9(2) ?
N13 C14 C16 . 122.1(3) ?
C15 C14 C16 . 131.9(3) ?
C14 C15 C11 . 106.8(2) ?
C14 C15 H15 . 126.6 ?
C11 C15 H15 . 126.6 ?
C14 C16 H16A . 109.5 ?
C14 C16 H16B . 109.5 ?
H16A C16 H16B . 109.5 ?
C14 C16 H16C . 109.5 ?
H16A C16 H16C . 109.5 ?
H16B C16 H16C . 109.5 ?
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
Cd1 N12 . 2.280(2) y
Cd1 N1 . 2.289(2) y
Cd1 Cl3 . 2.4533(7) y
Cd1 Cl2 . 2.5783(6) y
Cd1 Cl2 2_666 2.6600(7) y
N1 C9 . 1.325(3) ?
N1 C2 . 1.397(3) ?
N8 C9 . 1.348(3) ?
N8 C7 . 1.378(4) ?
N8 H8 . 0.8600 ?
N12 C11 . 1.328(3) ?
N12 N13 . 1.360(3) ?
N13 C14 . 1.337(4) ?
N13 H13 . 0.8600 ?
C2 C3 . 1.386(4) ?
C2 C7 . 1.394(3) ?
C3 C4 . 1.378(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.392(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.372(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.389(4) ?
C6 H6 . 0.9300 ?
C9 C10 . 1.486(4) ?
C10 C11 . 1.492(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C15 . 1.395(4) ?
C14 C15 . 1.364(4) ?
C14 C16 . 1.486(4) ?
C15 H15 . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
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
N8 H8 Cl2 2_656 0.86 2.66 3.345(2) 137.1
N8 H8 Cl3 2_556 0.86 2.99 3.633(2) 133.6
N13 H13 Cl3 2_566 0.86 2.58 3.369(2) 153.6
N13 H13 Cl2 2_666 0.86 2.86 3.295(2) 113.1
