##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2012-05-18
_journal_date_accepted     2012-06-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      7
_journal_page_first     m948
_journal_page_last     m948
_journal_paper_category     QM
_journal_paper_doi     10.1107/S1600536812026712
_journal_coeditor_code     VM2178
_publ_contact_author_name     'Dr. Haiyan Yang'
_publ_contact_author_address
;
 School of Materials and Chemical Engineering
 Zhongyuan University of Technology
 Zhengzhou 450007
 People's Republic of China
;
_publ_contact_author_email     'yanghy2009@yahoo.com.cn'
_publ_contact_author_fax     '86 371 62506687'
_publ_contact_author_phone     '86 371 62506687'
_publ_section_title
;\
Bis{1-[(1H-benzotriazol-1-yl)methyl]-2-methyl-1H-imidazole-\
κN³}dichloridocobalt(II)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Haiyan Yang' ?
;
 School of Materials and Chemical Engineering
 Zhongyuan University of Technology
 Zhengzhou 450007
 People's Republic of China
;
    'Yinghua Li' ?
;
 School of Materials and Chemical Engineering
 Zhongyuan University of Technology
 Zhengzhou 450007
 People's Republic of China
;
    'Yaomin Zhao' ?
;
 School of Materials and Chemical Engineering
 Zhongyuan University of Technology
 Zhengzhou 450007
 People's Republic of China
;
    'Wenzhuo Li' ?
;
 School of Materials and Chemical Engineering
 Zhongyuan University of Technology
 Zhengzhou 450007
 People's Republic of China
;
    'Fang He' ?
;
 School of Materials and Chemical Engineering
 Zhongyuan University of Technology
 Zhengzhou 450007
 People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Bis{1-[(1H-benzotriazol-1-yl)methyl]-2-methyl-1H-imidazole-
κN³}dichloridocobalt(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H22 Cl2 Co N10'
_chemical_formula_sum     'C22 H22 Cl2 Co N10'
_chemical_formula_iupac     '[Co Cl2 (C11 H11 N5)2]'
_chemical_formula_weight     556.33
_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     8.1684(16)
_cell_length_b     12.691(3)
_cell_length_c     13.289(3)
_cell_angle_alpha     65.48(3)
_cell_angle_beta     79.66(3)
_cell_angle_gamma     84.30(3)
_cell_volume     1232.5(6)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3451
_cell_measurement_theta_min     2.5355
_cell_measurement_theta_max     29.1686
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.499
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     570
_exptl_absorpt_coefficient_mu     0.946
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details     '(CrystalClear; Rigaku/MSC, 2006)'
_exptl_absorpt_correction_T_min     0.8189
_exptl_absorpt_correction_T_max     0.8482
_exptl_special_details     ?
_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     'Rigaku Saturn'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     28.5714
_diffrn_reflns_number     12593
_diffrn_reflns_av_R_equivalents     0.0392
_diffrn_reflns_av_sigmaI/netI     0.0478
_diffrn_reflns_theta_min     2.54
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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     4330
_reflns_number_gt     3512
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0657
_refine_ls_R_factor_gt     0.0492
_refine_ls_wR_factor_gt     0.0936
_refine_ls_wR_factor_ref     0.1007
_refine_ls_goodness_of_fit_ref     1.077
_refine_ls_restrained_S_all     1.077
_refine_ls_number_reflns     4330
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0391P)²+0.5956P] 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     0.265
_refine_diff_density_min     -0.234
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0016(4)
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'
    'Co' 'Co' 0.3494 0.9721
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrystalClear (Rigaku/MSC, 2006)'
_computing_cell_refinement     'CrystalClear (Rigaku/MSC, 2006)'
_computing_data_reduction     'CrystalClear (Rigaku/MSC, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Co Co1 0.74031(5) 0.25471(4) 1.02928(4) 0.03397(15) Uani d . 1 1 . .
    Cl Cl2 0.96039(10) 0.29359(8) 1.08673(7) 0.0442(2) Uani d . 1 1 . .
    Cl Cl1 0.54177(11) 0.15986(8) 1.17231(7) 0.0499(3) Uani d . 1 1 . .
    N N10 0.8046(3) 0.1424(2) 0.9553(2) 0.0355(6) Uani d . 1 1 . .
    N N9 0.9277(3) 0.0521(2) 0.8515(2) 0.0361(6) Uani d . 1 1 . .
    N N8 0.5347(3) 0.5454(2) 0.7929(2) 0.0347(6) Uani d . 1 1 . .
    N N7 0.6681(3) 0.4063(2) 0.9140(2) 0.0356(6) Uani d . 1 1 . .
    N N6 0.3355(3) 0.5794(2) 0.6656(2) 0.0366(6) Uani d . 1 1 . .
    N N5 1.0308(3) 0.0933(2) 0.6572(2) 0.0355(6) Uani d . 1 1 . .
    N N4 0.1979(4) 0.5126(3) 0.7064(2) 0.0506(8) Uani d . 1 1 . .
    C C22 0.5192(4) 0.4454(3) 0.8859(3) 0.0341(7) Uani d . 1 1 . .
    C C21 0.3696(4) 0.6166(3) 0.5519(3) 0.0351(8) Uani d . 1 1 . .
    C C20 1.0485(4) 0.0219(3) 0.7720(3) 0.0402(8) Uani d . 1 1 . .
    H H20A 1.1599 0.0296 0.7836 0.048 Uiso calc R 1 1 . .
    H H20B 1.0357 -0.0585 0.7865 0.048 Uiso calc R 1 1 . .
    C C19 0.9193(4) 0.0867(3) 0.5953(3) 0.0355(8) Uani d . 1 1 . .
    C C18 0.7811(4) 0.4857(3) 0.8355(3) 0.0412(8) Uani d . 1 1 . .
    H H18 0.8957 0.4805 0.8347 0.049 Uiso calc R 1 1 . .
    C C17 1.0626(4) 0.2316(3) 0.8261(3) 0.0518(10) Uani d . 1 1 . .
    H H17A 1.0585 0.2762 0.8698 0.078 Uiso calc R 1 1 . .
    H H17B 1.0434 0.2820 0.7517 0.078 Uiso calc R 1 1 . .
    H H17C 1.1701 0.1939 0.8228 0.078 Uiso calc R 1 1 . .
    N N3 1.1490(4) 0.1713(3) 0.5909(3) 0.0506(8) Uani d . 1 1 . .
    C C16 0.7157(4) 0.0454(3) 0.9789(3) 0.0458(9) Uani d . 1 1 . .
    H H16 0.6192 0.0222 1.0307 0.055 Uiso calc R 1 1 . .
    C C15 0.9326(4) 0.1432(3) 0.8783(3) 0.0336(7) Uani d . 1 1 . .
    C C14 0.7008(4) 0.5706(3) 0.7612(3) 0.0431(9) Uani d . 1 1 . .
    H H14 0.7478 0.6343 0.7001 0.052 Uiso calc R 1 1 . .
    C C13 0.3999(4) 0.6178(3) 0.7388(3) 0.0412(8) Uani d . 1 1 . .
    H H13A 0.3096 0.6206 0.7962 0.049 Uiso calc R 1 1 . .
    H H13B 0.4391 0.6960 0.6957 0.049 Uiso calc R 1 1 . .
    N N2 0.1465(4) 0.5038(3) 0.6233(3) 0.0545(8) Uani d . 1 1 . .
    C C12 0.9755(4) 0.1649(3) 0.4876(3) 0.0429(9) Uani d . 1 1 . .
    N N1 1.1164(4) 0.2153(3) 0.4899(3) 0.0561(9) Uani d . 1 1 . .
    C C11 0.4878(4) 0.6888(3) 0.4702(3) 0.0516(10) Uani d . 1 1 . .
    H H11 0.5704 0.7210 0.4876 0.062 Uiso calc R 1 1 . .
    C C10 0.2473(4) 0.5673(3) 0.5262(3) 0.0409(8) Uani d . 1 1 . .
    C C9 0.3583(4) 0.3907(3) 0.9458(3) 0.0548(10) Uani d . 1 1 . .
    H H9A 0.3199 0.3536 0.9047 0.082 Uiso calc R 1 1 . .
    H H9B 0.2778 0.4489 0.9524 0.082 Uiso calc R 1 1 . .
    H H9C 0.3727 0.3341 1.0190 0.082 Uiso calc R 1 1 . .
    C C8 0.7901(4) -0.0098(3) 0.9155(3) 0.0477(9) Uani d . 1 1 . .
    H H8 0.7552 -0.0771 0.9150 0.057 Uiso calc R 1 1 . .
    C C7 0.7637(6) 0.1099(4) 0.4233(4) 0.0684(13) Uani d . 1 1 . .
    H H7 0.7086 0.1153 0.3658 0.082 Uiso calc R 1 1 . .
    C C6 0.7829(4) 0.0189(3) 0.6201(3) 0.0506(9) Uani d . 1 1 . .
    H H6 0.7453 -0.0331 0.6926 0.061 Uiso calc R 1 1 . .
    C C5 0.7071(5) 0.0326(4) 0.5325(4) 0.0657(12) Uani d . 1 1 . .
    H H5 0.6143 -0.0109 0.5456 0.079 Uiso calc R 1 1 . .
    C C4 0.2367(5) 0.5902(4) 0.4153(3) 0.0541(10) Uani d . 1 1 . .
    H H4 0.1549 0.5580 0.3973 0.065 Uiso calc R 1 1 . .
    C C3 0.8964(6) 0.1772(4) 0.3983(3) 0.0606(11) Uani d . 1 1 . .
    H H3 0.9330 0.2290 0.3255 0.073 Uiso calc R 1 1 . .
    C C2 0.3513(5) 0.6615(4) 0.3352(3) 0.0623(11) Uani d . 1 1 . .
    H H2 0.3476 0.6788 0.2604 0.075 Uiso calc R 1 1 . .
    C C1 0.4746(5) 0.7095(4) 0.3621(3) 0.0645(12) Uani d . 1 1 . .
    H H1 0.5510 0.7575 0.3043 0.077 Uiso calc R 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    Co1 N7 . 2.012(3) ?
    Co1 N10 . 2.026(3) ?
    Co1 Cl2 . 2.2449(10) ?
    Co1 Cl1 . 2.2527(14) ?
    N10 C15 . 1.323(4) ?
    N10 C16 . 1.385(4) ?
    N9 C15 . 1.350(4) ?
    N9 C8 . 1.372(4) ?
    N9 C20 . 1.457(4) ?
    N8 C22 . 1.351(4) ?
    N8 C14 . 1.375(4) ?
    N8 C13 . 1.452(4) ?
    N7 C22 . 1.324(4) ?
    N7 C18 . 1.387(4) ?
    N6 N4 . 1.365(4) ?
    N6 C21 . 1.366(4) ?
    N6 C13 . 1.446(4) ?
    N5 N3 . 1.360(4) ?
    N5 C19 . 1.361(4) ?
    N5 C20 . 1.441(4) ?
    N4 N2 . 1.298(4) ?
    C22 C9 . 1.480(4) ?
    C21 C10 . 1.390(4) ?
    C21 C11 . 1.387(5) ?
    C20 H20A . 0.9700 ?
    C20 H20B . 0.9700 ?
    C19 C6 . 1.383(4) ?
    C19 C12 . 1.386(4) ?
    C18 C14 . 1.332(5) ?
    C18 H18 . 0.9300 ?
    C17 C15 . 1.480(4) ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    N3 N1 . 1.289(4) ?
    C16 C8 . 1.339(5) ?
    C16 H16 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    N2 C10 . 1.371(4) ?
    C12 N1 . 1.381(5) ?
    C12 C3 . 1.396(5) ?
    C11 C1 . 1.372(5) ?
    C11 H11 . 0.9300 ?
    C10 C4 . 1.396(5) ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C8 H8 . 0.9300 ?
    C7 C3 . 1.355(6) ?
    C7 C5 . 1.397(6) ?
    C7 H7 . 0.9300 ?
    C6 C5 . 1.355(5) ?
    C6 H6 . 0.9300 ?
    C5 H5 . 0.9300 ?
    C4 C2 . 1.357(5) ?
    C4 H4 . 0.9300 ?
    C3 H3 . 0.9300 ?
    C2 C1 . 1.395(6) ?
    C2 H2 . 0.9300 ?
    C1 H1 . 0.9300 ?
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
    N7 Co1 N10 . . 108.31(11) ?
    N7 Co1 Cl2 . . 106.00(8) ?
    N10 Co1 Cl2 . . 111.09(8) ?
    N7 Co1 Cl1 . . 115.96(8) ?
    N10 Co1 Cl1 . . 102.74(8) ?
    Cl2 Co1 Cl1 . . 112.73(4) ?
    C15 N10 C16 . . 106.0(3) ?
    C15 N10 Co1 . . 129.7(2) ?
    C16 N10 Co1 . . 124.2(2) ?
    C15 N9 C8 . . 107.5(3) ?
    C15 N9 C20 . . 126.7(3) ?
    C8 N9 C20 . . 125.7(3) ?
    C22 N8 C14 . . 108.1(3) ?
    C22 N8 C13 . . 126.5(3) ?
    C14 N8 C13 . . 125.4(3) ?
    C22 N7 C18 . . 106.3(3) ?
    C22 N7 Co1 . . 130.8(2) ?
    C18 N7 Co1 . . 122.4(2) ?
    N4 N6 C21 . . 110.0(3) ?
    N4 N6 C13 . . 118.9(3) ?
    C21 N6 C13 . . 129.8(3) ?
    N3 N5 C19 . . 110.3(3) ?
    N3 N5 C20 . . 119.8(3) ?
    C19 N5 C20 . . 129.4(3) ?
    N2 N4 N6 . . 108.5(3) ?
    N7 C22 N8 . . 109.6(3) ?
    N7 C22 C9 . . 126.4(3) ?
    N8 C22 C9 . . 124.0(3) ?
    N6 C21 C10 . . 103.9(3) ?
    N6 C21 C11 . . 133.7(3) ?
    C10 C21 C11 . . 122.3(3) ?
    N5 C20 N9 . . 112.9(3) ?
    N5 C20 H20A . . 109.0 ?
    N9 C20 H20A . . 109.0 ?
    N5 C20 H20B . . 109.0 ?
    N9 C20 H20B . . 109.0 ?
    H20A C20 H20B . . 107.8 ?
    N5 C19 C6 . . 133.5(3) ?
    N5 C19 C12 . . 104.1(3) ?
    C6 C19 C12 . . 122.3(3) ?
    C14 C18 N7 . . 109.7(3) ?
    C14 C18 H18 . . 125.1 ?
    N7 C18 H18 . . 125.1 ?
    C15 C17 H17A . . 109.5 ?
    C15 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C15 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    N1 N3 N5 . . 108.6(3) ?
    C8 C16 N10 . . 109.4(3) ?
    C8 C16 H16 . . 125.3 ?
    N10 C16 H16 . . 125.3 ?
    N10 C15 N9 . . 110.3(3) ?
    N10 C15 C17 . . 125.8(3) ?
    N9 C15 C17 . . 123.9(3) ?
    C18 C14 N8 . . 106.3(3) ?
    C18 C14 H14 . . 126.8 ?
    N8 C14 H14 . . 126.8 ?
    N6 C13 N8 . . 114.5(3) ?
    N6 C13 H13A . . 108.6 ?
    N8 C13 H13A . . 108.6 ?
    N6 C13 H13B . . 108.6 ?
    N8 C13 H13B . . 108.6 ?
    H13A C13 H13B . . 107.6 ?
    N4 N2 C10 . . 108.7(3) ?
    N1 C12 C19 . . 108.3(3) ?
    N1 C12 C3 . . 130.9(4) ?
    C19 C12 C3 . . 120.7(4) ?
    N3 N1 C12 . . 108.7(3) ?
    C1 C11 C21 . . 115.5(3) ?
    C1 C11 H11 . . 122.2 ?
    C21 C11 H11 . . 122.2 ?
    N2 C10 C21 . . 108.9(3) ?
    N2 C10 C4 . . 130.2(3) ?
    C21 C10 C4 . . 120.9(3) ?
    C22 C9 H9A . . 109.5 ?
    C22 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C22 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C16 C8 N9 . . 106.7(3) ?
    C16 C8 H8 . . 126.6 ?
    N9 C8 H8 . . 126.6 ?
    C3 C7 C5 . . 122.1(4) ?
    C3 C7 H7 . . 119.0 ?
    C5 C7 H7 . . 119.0 ?
    C5 C6 C19 . . 116.2(4) ?
    C5 C6 H6 . . 121.9 ?
    C19 C6 H6 . . 121.9 ?
    C6 C5 C7 . . 122.2(4) ?
    C6 C5 H5 . . 118.9 ?
    C7 C5 H5 . . 118.9 ?
    C2 C4 C10 . . 117.0(3) ?
    C2 C4 H4 . . 121.5 ?
    C10 C4 H4 . . 121.5 ?
    C7 C3 C12 . . 116.6(4) ?
    C7 C3 H3 . . 121.7 ?
    C12 C3 H3 . . 121.7 ?
    C4 C2 C1 . . 121.6(4) ?
    C4 C2 H2 . . 119.2 ?
    C1 C2 H2 . . 119.2 ?
    C11 C1 C2 . . 122.7(4) ?
    C11 C1 H1 . . 118.7 ?
    C2 C1 H1 . . 118.7 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N7 Co1 N10 C15 . . . . 68.8(3) ?
    Cl2 Co1 N10 C15 . . . . -47.3(3) ?
    Cl1 Co1 N10 C15 . . . . -168.0(3) ?
    N7 Co1 N10 C16 . . . . -111.3(3) ?
    Cl2 Co1 N10 C16 . . . . 132.7(2) ?
    Cl1 Co1 N10 C16 . . . . 11.9(3) ?
    N10 Co1 N7 C22 . . . . 91.0(3) ?
    Cl2 Co1 N7 C22 . . . . -149.7(3) ?
    Cl1 Co1 N7 C22 . . . . -23.8(3) ?
    N10 Co1 N7 C18 . . . . -79.4(3) ?
    Cl2 Co1 N7 C18 . . . . 39.9(3) ?
    Cl1 Co1 N7 C18 . . . . 165.8(2) ?
    C21 N6 N4 N2 . . . . 1.7(4) ?
    C13 N6 N4 N2 . . . . 169.9(3) ?
    C18 N7 C22 N8 . . . . 0.4(4) ?
    Co1 N7 C22 N8 . . . . -171.2(2) ?
    C18 N7 C22 C9 . . . . -179.2(3) ?
    Co1 N7 C22 C9 . . . . 9.2(5) ?
    C14 N8 C22 N7 . . . . -0.3(4) ?
    C13 N8 C22 N7 . . . . -177.0(3) ?
    C14 N8 C22 C9 . . . . 179.3(3) ?
    C13 N8 C22 C9 . . . . 2.7(5) ?
    N4 N6 C21 C10 . . . . -1.0(3) ?
    C13 N6 C21 C10 . . . . -167.6(3) ?
    N4 N6 C21 C11 . . . . 176.8(4) ?
    C13 N6 C21 C11 . . . . 10.2(6) ?
    N3 N5 C20 N9 . . . . 110.2(3) ?
    C19 N5 C20 N9 . . . . -79.0(4) ?
    C15 N9 C20 N5 . . . . -77.1(4) ?
    C8 N9 C20 N5 . . . . 105.0(4) ?
    N3 N5 C19 C6 . . . . 176.6(4) ?
    C20 N5 C19 C6 . . . . 5.1(6) ?
    N3 N5 C19 C12 . . . . 0.0(3) ?
    C20 N5 C19 C12 . . . . -171.5(3) ?
    C22 N7 C18 C14 . . . . -0.4(4) ?
    Co1 N7 C18 C14 . . . . 172.1(2) ?
    C19 N5 N3 N1 . . . . 0.6(4) ?
    C20 N5 N3 N1 . . . . 173.0(3) ?
    C15 N10 C16 C8 . . . . -0.5(4) ?
    Co1 N10 C16 C8 . . . . 179.6(2) ?
    C16 N10 C15 N9 . . . . 0.5(4) ?
    Co1 N10 C15 N9 . . . . -179.5(2) ?
    C16 N10 C15 C17 . . . . 179.5(3) ?
    Co1 N10 C15 C17 . . . . -0.5(5) ?
    C8 N9 C15 N10 . . . . -0.4(4) ?
    C20 N9 C15 N10 . . . . -178.6(3) ?
    C8 N9 C15 C17 . . . . -179.4(3) ?
    C20 N9 C15 C17 . . . . 2.4(5) ?
    N7 C18 C14 N8 . . . . 0.2(4) ?
    C22 N8 C14 C18 . . . . 0.0(4) ?
    C13 N8 C14 C18 . . . . 176.8(3) ?
    N4 N6 C13 N8 . . . . 95.8(4) ?
    C21 N6 C13 N8 . . . . -98.6(4) ?
    C22 N8 C13 N6 . . . . -81.8(4) ?
    C14 N8 C13 N6 . . . . 102.0(4) ?
    N6 N4 N2 C10 . . . . -1.6(4) ?
    N5 C19 C12 N1 . . . . -0.5(4) ?
    C6 C19 C12 N1 . . . . -177.7(3) ?
    N5 C19 C12 C3 . . . . 176.2(3) ?
    C6 C19 C12 C3 . . . . -0.9(5) ?
    N5 N3 N1 C12 . . . . -0.9(4) ?
    C19 C12 N1 N3 . . . . 0.9(4) ?
    C3 C12 N1 N3 . . . . -175.4(4) ?
    N6 C21 C11 C1 . . . . -176.7(4) ?
    C10 C21 C11 C1 . . . . 0.8(5) ?
    N4 N2 C10 C21 . . . . 0.9(4) ?
    N4 N2 C10 C4 . . . . -175.8(4) ?
    N6 C21 C10 N2 . . . . 0.1(4) ?
    C11 C21 C10 N2 . . . . -178.1(3) ?
    N6 C21 C10 C4 . . . . 177.2(3) ?
    C11 C21 C10 C4 . . . . -1.0(5) ?
    N10 C16 C8 N9 . . . . 0.2(4) ?
    C15 N9 C8 C16 . . . . 0.1(4) ?
    C20 N9 C8 C16 . . . . 178.3(3) ?
    N5 C19 C6 C5 . . . . -175.7(4) ?
    C12 C19 C6 C5 . . . . 0.4(5) ?
    C19 C6 C5 C7 . . . . 0.5(6) ?
    C3 C7 C5 C6 . . . . -1.0(7) ?
    N2 C10 C4 C2 . . . . 176.8(4) ?
    C21 C10 C4 C2 . . . . 0.4(6) ?
    C5 C7 C3 C12 . . . . 0.5(6) ?
    N1 C12 C3 C7 . . . . 176.3(4) ?
    C19 C12 C3 C7 . . . . 0.4(5) ?
    C10 C4 C2 C1 . . . . 0.3(6) ?
    C21 C11 C1 C2 . . . . -0.1(6) ?
    C4 C2 C1 C11 . . . . -0.4(7) ?
