##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2003-05-27
_journal_date_accepted     2003-06-20
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2003
_journal_volume     59
_journal_issue      8
_journal_page_first     m334
_journal_page_last     m336
_journal_paper_category     FM
_publ_contact_author_name     'Marcel Pierrot '
_publ_contact_author_address
;
     LBS-UMR 6517
     Faculté des Sciences  et Techniques de Saint Jérôme
     Avenue Escadrille Normandie Niemen
     13397 Marseille Cedex 20
     France
;
_publ_contact_author_email     'marcel.pierrot@lbs.u-3mrs.fr'
_publ_contact_author_fax     '(33) 4 91 98 32 08'
_publ_contact_author_phone     '(33) 4 91 28 84 24'
_publ_section_title
;
Complexation du 2-[(5-méthylpyrazolyl)méthyle]benzimidazole
par les chlorures de cuivre et de cadmium
;
loop_
    _publ_author_name
    _publ_author_address
    'Sbai, F.'
;    Laboratoire de chimie organique,
        Faculté des Sciences , Université Mohamed V,
        Rabat, Maroc
;
    '  Regragui, R.  '
;    Laboratoire de chimie organique,
        Faculté des Sciences , Université Mohamed V,
        Rabat, Maroc
;
    '  Essassi, E., M.  '
;    Laboratoire de chimie organique,
        Faculté des Sciences , Université Mohamed V,
        Rabat, Maroc
;
    'Kenz, A.'
;   LBS-UMR 6517, Centre Scientifique Saint-Jérôme,
        13397 Marseille, Cedex 20 , France
;
    'Pierrot, M.'
;   LBS-UMR 6517, Centre Scientifique Saint-Jérôme,
        13397 Marseille, Cedex 20 , France
;
_publ_section_synopsis
;
A mixture of copper chloride dissolved in acetone and added to a solution
of ligand L, where L is 2-[(5-methylpyrazolyl)methyle)]benzimidazole, in
acetone gives rise to green crystals of [CuCl₂(C₁₂H₁₂N₄)].
[Cd₂Cl₄(C₁₂H₁₂N₄)₂] is
obtained by adding cadmium chloride dissolved in methanol to a solution
of the same ligand L in methanol. The yellow powder is then crystallized
in ethanol.
;
data_I
_chemical_name_systematic
;
?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H12 Cu1 Cl2 N4'
_chemical_formula_sum     'C12 H12 Cl2 Cu1 N4'
_chemical_formula_iupac     '[Cu Cl2 (C12 H12 N4)]'
_chemical_formula_weight     346.70
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 1 21/c 1'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     13.4356(6)
_cell_length_b     7.2183(2)
_cell_length_c     16.0421(6)
_cell_angle_alpha     90.0
_cell_angle_beta     118.510(2)
_cell_angle_gamma     90.0
_cell_volume     1367.11(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9873
_cell_measurement_theta_min     2
_cell_measurement_theta_max     26.4
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Needle
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.075
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.684
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     700
_exptl_absorpt_coefficient_mu     1.978
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'KappaCCD'
_diffrn_measurement_method     'φ scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9873
_diffrn_reflns_av_R_equivalents     0.037
_diffrn_reflns_av_sigmaI/netI     0.0278
_diffrn_reflns_theta_min     2.56
_diffrn_reflns_theta_max     26.39
_diffrn_reflns_theta_full     26.39
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     0
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total     2744
_reflns_number_gt     2492
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0359
_refine_ls_R_factor_gt     0.0311
_refine_ls_wR_factor_gt     0.0746
_refine_ls_wR_factor_ref     0.0775
_refine_ls_goodness_of_fit_ref     1.066
_refine_ls_restrained_S_all     1.066
_refine_ls_number_reflns     2744
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0248P)²+1.7253P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.605
_refine_diff_density_min     -0.342
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    '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'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'KappaCCD (Nonius, 1998) '
_computing_data_reduction     'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
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 0.37965(2) 0.20934(4) 0.321607(19) 0.02965(11) Uani d . 1 . . Cu
    Cl2 0.27315(6) 0.41367(11) 0.20989(5) 0.04647(19) Uani d . 1 . . Cl
    Cl3 0.41050(7) 0.00258(10) 0.23329(4) 0.04723(19) Uani d . 1 . . Cl
    N1 0.31181(17) 0.2444(3) 0.40433(14) 0.0295(4) Uani d . 1 . . N
    N8 0.29066(19) 0.3038(3) 0.52960(15) 0.0359(5) Uani d . 1 . . N
    H8 0.3078 0.3292 0.5873 0.043 Uiso calc R 1 . . H
    N12 0.53108(17) 0.1884(3) 0.43342(14) 0.0303(4) Uani d . 1 . . N
    N13 0.62656(17) 0.1623(3) 0.42593(14) 0.0329(5) Uani d . 1 . . N
    H13 0.6270 0.1238 0.3754 0.040 Uiso calc R 1 . . H
    C2 0.1961(2) 0.2409(4) 0.37664(18) 0.0351(6) Uani d . 1 . . C
    C3 0.1033(2) 0.1962(5) 0.2904(2) 0.0512(8) Uani d . 1 . . C
    H3 0.1112 0.1686 0.2372 0.061 Uiso calc R 1 . . H
    C4 -0.0009(3) 0.1947(6) 0.2873(2) 0.0637(10) Uani d . 1 . . C
    H4 -0.0645 0.1630 0.2308 0.076 Uiso calc R 1 . . H
    C5 -0.0140(3) 0.2392(6) 0.3657(3) 0.0641(10) Uani d . 1 . . C
    H5 -0.0863 0.2396 0.3599 0.077 Uiso calc R 1 . . H
    C6 0.0774(3) 0.2825(5) 0.4519(2) 0.0534(8) Uani d . 1 . . C
    H6 0.0689 0.3121 0.5046 0.064 Uiso calc R 1 . . H
    C7 0.1829(2) 0.2798(4) 0.45596(18) 0.0364(6) Uani d . 1 . . C
    C9 0.3648(2) 0.2809(3) 0.49660(16) 0.0271(5) Uani d . 1 . . C
    C10 0.4887(2) 0.2950(3) 0.56127(16) 0.0291(5) Uani d . 1 . . C
    H10A 0.5072 0.2148 0.6152 0.035 Uiso calc R 1 . . H
    H10B 0.5050 0.4210 0.5851 0.035 Uiso calc R 1 . . H
    C11 0.5664(2) 0.2481(3) 0.52220(16) 0.0271(5) Uani d . 1 . . C
    C14 0.7199(2) 0.2036(4) 0.50669(19) 0.0357(6) Uani d . 1 . . C
    C15 0.6837(2) 0.2587(4) 0.57039(18) 0.0358(6) Uani d . 1 . . C
    H15 0.7289 0.2954 0.6330 0.043 Uiso calc R 1 . . H
    C16 0.8353(2) 0.1945(5) 0.5150(2) 0.0519(8) Uani d . 1 . . C
    H16A 0.8332 0.1174 0.4654 0.078 Uiso calc R 1 . . H
    H16B 0.8875 0.1433 0.5756 0.078 Uiso calc R 1 . . H
    H16C 0.8594 0.3169 0.5094 0.078 Uiso calc R 1 . . H
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 0.03491(17) 0.03676(19) 0.01630(15) 0.00303(13) 0.01142(12) 0.00022(11)
    Cl2 0.0541(4) 0.0574(4) 0.0315(3) 0.0205(3) 0.0234(3) 0.0169(3)
    Cl3 0.0739(5) 0.0424(4) 0.0234(3) 0.0169(3) 0.0216(3) 0.0010(3)
    N1 0.0304(10) 0.0379(11) 0.0194(9) -0.0011(9) 0.0113(8) 0.0010(8)
    N8 0.0398(12) 0.0494(14) 0.0227(10) -0.0007(10) 0.0184(9) -0.0026(9)
    N12 0.0326(11) 0.0353(11) 0.0228(10) 0.0023(9) 0.0131(8) -0.0006(8)
    N13 0.0361(11) 0.0388(12) 0.0271(10) -0.0007(9) 0.0176(9) -0.0024(9)
    C2 0.0338(13) 0.0441(15) 0.0282(12) -0.0019(11) 0.0154(11) 0.0023(11)
    C3 0.0381(15) 0.082(2) 0.0286(14) -0.0088(15) 0.0119(12) -0.0010(14)
    C4 0.0337(15) 0.105(3) 0.0420(17) -0.0099(17) 0.0096(13) 0.0064(18)
    C5 0.0342(16) 0.101(3) 0.059(2) -0.0012(17) 0.0236(15) 0.014(2)
    C6 0.0463(17) 0.078(2) 0.0468(17) 0.0038(16) 0.0306(15) 0.0055(16)
    C7 0.0363(13) 0.0453(15) 0.0279(12) -0.0007(11) 0.0155(11) 0.0024(11)
    C9 0.0360(12) 0.0253(11) 0.0215(11) -0.0002(9) 0.0148(10) 0.0012(9)
    C10 0.0353(12) 0.0313(12) 0.0190(11) 0.0012(10) 0.0115(10) -0.0001(9)
    C11 0.0346(12) 0.0234(11) 0.0210(11) 0.0005(9) 0.0113(9) 0.0022(8)
    C14 0.0348(13) 0.0367(14) 0.0366(14) -0.0017(11) 0.0179(11) 0.0005(11)
    C15 0.0339(13) 0.0414(14) 0.0273(12) -0.0020(11) 0.0106(10) -0.0042(11)
    C16 0.0377(15) 0.067(2) 0.0537(18) -0.0088(14) 0.0240(14) -0.0132(16)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 . 1.952(2) y
    Cu1 N12 . 1.974(2) y
    Cu1 Cl3 . 2.2286(7) y
    Cu1 Cl2 . 2.2331(8) y
    N1 C9 . 1.327(3) ?
    N1 C2 . 1.398(3) ?
    N8 C9 . 1.343(3) ?
    N8 C7 . 1.374(3) ?
    N8 H8 . 0.8600 ?
    N12 C11 . 1.340(3) ?
    N12 N13 . 1.357(3) ?
    N13 C14 . 1.337(3) ?
    N13 H13 . 0.8600 ?
    C2 C3 . 1.388(4) ?
    C2 C7 . 1.395(4) ?
    C3 C4 . 1.377(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.390(5) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.377(5) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.388(4) ?
    C6 H6 . 0.9300 ?
    C9 C10 . 1.486(3) ?
    C10 C11 . 1.490(3) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C15 . 1.387(3) ?
    C14 C15 . 1.383(4) ?
    C14 C16 . 1.493(4) ?
    C15 H15 . 0.9300 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 Cu1 N12 . . 90.31(8) y
    N1 Cu1 Cl3 . . 143.89(7) y
    N12 Cu1 Cl3 . . 95.90(6) y
    N1 Cu1 Cl2 . . 97.57(6) y
    N12 Cu1 Cl2 . . 140.13(7) y
    Cl3 Cu1 Cl2 . . 100.05(3) y
    C9 N1 C2 . . 106.3(2) ?
    C9 N1 Cu1 . . 127.43(17) ?
    C2 N1 Cu1 . . 126.21(16) ?
    C9 N8 C7 . . 108.7(2) ?
    C9 N8 H8 . . 125.6 ?
    C7 N8 H8 . . 125.6 ?
    C11 N12 N13 . . 105.60(19) ?
    C11 N12 Cu1 . . 129.04(17) ?
    N13 N12 Cu1 . . 122.54(15) ?
    C14 N13 N12 . . 111.8(2) ?
    C14 N13 H13 . . 124.1 ?
    N12 N13 H13 . . 124.1 ?
    C3 C2 C7 . . 120.8(2) ?
    C3 C2 N1 . . 130.8(2) ?
    C7 C2 N1 . . 108.2(2) ?
    C4 C3 C2 . . 116.8(3) ?
    C4 C3 H3 . . 121.6 ?
    C2 C3 H3 . . 121.6 ?
    C3 C4 C5 . . 122.1(3) ?
    C3 C4 H4 . . 118.9 ?
    C5 C4 H4 . . 118.9 ?
    C6 C5 C4 . . 121.6(3) ?
    C6 C5 H5 . . 119.2 ?
    C4 C5 H5 . . 119.2 ?
    C5 C6 C7 . . 116.5(3) ?
    C5 C6 H6 . . 121.8 ?
    C7 C6 H6 . . 121.8 ?
    N8 C7 C6 . . 132.2(3) ?
    N8 C7 C2 . . 105.6(2) ?
    C6 C7 C2 . . 122.1(3) ?
    N1 C9 N8 . . 111.1(2) ?
    N1 C9 C10 . . 128.2(2) ?
    N8 C9 C10 . . 120.7(2) ?
    C9 C10 C11 . . 117.8(2) ?
    C9 C10 H10A . . 107.9 ?
    C11 C10 H10A . . 107.9 ?
    C9 C10 H10B . . 107.9 ?
    C11 C10 H10B . . 107.9 ?
    H10A C10 H10B . . 107.2 ?
    N12 C11 C15 . . 110.0(2) ?
    N12 C11 C10 . . 123.8(2) ?
    C15 C11 C10 . . 126.2(2) ?
    N13 C14 C15 . . 106.4(2) ?
    N13 C14 C16 . . 122.0(2) ?
    C15 C14 C16 . . 131.5(3) ?
    C14 C15 C11 . . 106.2(2) ?
    C14 C15 H15 . . 126.9 ?
    C11 C15 H15 . . 126.9 ?
    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_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 Cl3 4_566 0.86 2.40 3.194(2) 152.9
    N8 H8 Cl2 4_566 0.86 2.83 3.396(2) 124.5
    N13 H13 Cl2 2_645 0.86 2.78 3.548(2) 149.6
    N13 H13 Cl3 . 0.86 2.84 3.278(2) 113.0
data_II
_chemical_name_systematic
;
?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H24 Cd2 Cl4 N8'
_chemical_formula_sum     'C24 H24 Cd2 Cl4 N8'
_chemical_formula_iupac     '[Cd2 Cl4 (C12 H12 N4)2]'
_chemical_formula_weight     791.13
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.8306(2)
_cell_length_b     9.7979(3)
_cell_length_c     10.1976(4)
_cell_angle_alpha     92.8610(10)
_cell_angle_beta     112.0140(10)
_cell_angle_gamma     105.4930(10)
_cell_volume     689.07(4)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     10163
_cell_measurement_theta_min     2
_cell_measurement_theta_max     26.
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.906
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     388
_exptl_absorpt_coefficient_mu     1.962
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'KappaCCD'
_diffrn_measurement_method     'φ scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10163
_diffrn_reflns_av_R_equivalents     0.027
_diffrn_reflns_av_sigmaI/netI     0.0264
_diffrn_reflns_theta_min     2.82
_diffrn_reflns_theta_max     26.
_diffrn_reflns_theta_full     26.46
_diffrn_measured_fraction_theta_max     0.917
_diffrn_measured_fraction_theta_full     0.917
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total     2614
_reflns_number_gt     2474
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0236
_refine_ls_R_factor_gt     0.0215
_refine_ls_wR_factor_gt     0.0495
_refine_ls_wR_factor_ref     0.0511
_refine_ls_goodness_of_fit_ref     1.092
_refine_ls_restrained_S_all     1.092
_refine_ls_number_reflns     2614
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0041P)²+0.8027P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.346
_refine_diff_density_min     -0.473
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'KappaCCD (Nonius, 1998) '
_computing_data_reduction     'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
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_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
    Cd1 0.03186(11) 0.02158(11) 0.03359(11) 0.00968(7) 0.01548(8) 0.01136(8)
    Cl3 0.0408(4) 0.0419(4) 0.0461(4) 0.0201(3) 0.0090(3) 0.0142(3)
    Cl2 0.0427(3) 0.0232(3) 0.0500(4) 0.0088(3) 0.0294(3) 0.0076(3)
    N1 0.0311(10) 0.0206(11) 0.0367(11) 0.0096(8) 0.0155(9) 0.0093(9)
    N8 0.0397(12) 0.0211(12) 0.0405(12) 0.0122(9) 0.0135(10) 0.0114(10)
    N12 0.0468(13) 0.0263(12) 0.0339(11) 0.0157(10) 0.0211(10) 0.0120(10)
    N13 0.0513(14) 0.0282(13) 0.0413(13) 0.0192(11) 0.0247(11) 0.0131(10)
    C2 0.0262(12) 0.0217(13) 0.0382(13) 0.0073(10) 0.0131(10) 0.0053(11)
    C3 0.0437(15) 0.0284(15) 0.0420(15) 0.0104(12) 0.0208(13) 0.0099(12)
    C4 0.0474(16) 0.0350(17) 0.0404(15) 0.0082(13) 0.0200(13) 0.0034(13)
    C5 0.0453(16) 0.0326(17) 0.0482(17) 0.0103(13) 0.0176(14) -0.0040(14)
    C6 0.0463(16) 0.0254(15) 0.0527(17) 0.0157(12) 0.0173(14) 0.0069(13)
    C7 0.0276(12) 0.0249(14) 0.0387(14) 0.0083(10) 0.0108(11) 0.0075(11)
    C9 0.0231(11) 0.0205(13) 0.0393(13) 0.0067(9) 0.0115(10) 0.0092(11)
    C10 0.0403(14) 0.0235(14) 0.0375(14) 0.0105(11) 0.0161(12) 0.0139(11)
    C11 0.0271(12) 0.0258(14) 0.0348(13) 0.0080(10) 0.0144(10) 0.0126(11)
    C14 0.0377(14) 0.0347(16) 0.0407(15) 0.0105(12) 0.0202(12) 0.0095(13)
    C15 0.0447(15) 0.0350(16) 0.0386(14) 0.0154(12) 0.0225(12) 0.0175(13)
    C16 0.062(2) 0.045(2) 0.0484(17) 0.0190(16) 0.0327(16) 0.0077(15)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _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_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
