##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. 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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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-03-21
_journal_date_accepted     2007-04-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      5
_journal_page_first     m1482
_journal_page_last     m1483
_journal_paper_category     EM
_journal_coeditor_code     DN2154
_publ_contact_author_name     'Dr. Li,  Qing-Xiang'
_publ_contact_author_address
;
Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology,
Wuhan Institute of Technology
Wuhan 430073
P.R.CHINA
;
_publ_contact_author_email     lqxwh@yahoo.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     '0086-027-87195749'
_publ_section_title
;\
[(4RS,7SR)-1-(1H-Benzimidazol-2-ylmethyl-κN³)-1,\
4,7-triazacyclononane-κ³N]bromidocopper(II) bromide
;
loop_
    _publ_author_name
    _publ_author_address
    'Li, Qing-Xiang'
;
Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology,
Wuhan Institute of Technology
Wuhan 430073
People's Republic of China
;
    'Bing-Zhong He'
;
Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology,
Wuhan Institute of Technology
Wuhan 430073
People's Republic of China
;
    'Jun-Yun Shen'
;
Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology,
Wuhan Institute of Technology
Wuhan 430073
People's Republic of China
;
    'Hai-Yan Xiao'
;
Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology,
Wuhan Institute of Technology
Wuhan 430073
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
[(4RS,7SR)-1-(1H-Benzimidazol-2-ylmethyl-\kN³)-1,4,7-triazacyclononane-
κ³N]bromidocopper(II) bromide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H21 Br Cu N5 +, Br -'
_chemical_formula_sum     'C14 H21 Br2 Cu N5'
_chemical_formula_iupac     '[Cu Br (C14 H21 N5)] Br'
_chemical_formula_weight     482.72
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
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'
_cell_length_a     19.525(2)
_cell_length_b     7.9390(9)
_cell_length_c     11.2702(12)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1747.0(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4123
_cell_measurement_theta_min     2.76
_cell_measurement_theta_max     24.20
_cell_measurement_temperature     297(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.835
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     956
_exptl_absorpt_coefficient_mu     5.828
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2001)'
_exptl_absorpt_correction_T_min     0.3886
_exptl_absorpt_correction_T_max     0.5934
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine focus sealed Siemens Mo tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     '0.3° wide ω exposures'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12313
_diffrn_reflns_av_R_equivalents     0.0360
_diffrn_reflns_av_sigmaI/netI     0.0491
_diffrn_reflns_theta_min     2.09
_diffrn_reflns_theta_max     26.99
_diffrn_reflns_theta_full     26.99
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_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 > 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     3796
_reflns_number_gt     3268
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0431
_refine_ls_R_factor_gt     0.0348
_refine_ls_wR_factor_gt     0.0763
_refine_ls_wR_factor_ref     0.0797
_refine_ls_goodness_of_fit_ref     1.003
_refine_ls_restrained_S_all     1.003
_refine_ls_number_reflns     3796
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0378P)²] 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     0.743
_refine_diff_density_min     -0.284
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1789 Friedel pairs measured'
_refine_ls_abs_structure_Flack     0.017(12)
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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
_computing_data_collection     'SMART (Bruker, 2001'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'PLATON (Spek, 2003)'
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_disorder_assembly
    _atom_site_disorder_group
    Cu Cu1 0.15537(2) -0.08222(6) 0.58863(4) 0.03287(12) Uani d . 1 . .
    Br Br1 0.14746(3) -0.35578(6) 0.68282(5) 0.06084(16) Uani d . 1 . .
    Br Br2 0.40028(2) 0.01195(6) 0.77450(6) 0.04833(13) Uani d . 1 . .
    C C1 0.2037(2) 0.2360(6) 0.4789(4) 0.0445(10) Uani d . 1 . .
    H H1A 0.2271 0.2142 0.4045 0.053 Uiso calc R 1 . .
    H H1B 0.1928 0.3551 0.4817 0.053 Uiso calc R 1 . .
    C C2 0.2506(2) 0.1952(7) 0.5783(4) 0.0512(12) Uani d . 1 . .
    H H2A 0.2320 0.2420 0.6510 0.061 Uiso calc R 1 . .
    H H2B 0.2946 0.2481 0.5639 0.061 Uiso calc R 1 . .
    C C3 0.2983(3) -0.0715(9) 0.4959(5) 0.0679(16) Uani d . 1 . .
    H H3A 0.3433 -0.1059 0.5234 0.081 Uiso calc R 1 . .
    H H3B 0.3046 0.0085 0.4317 0.081 Uiso calc R 1 . .
    C C4 0.2606(3) -0.2218(8) 0.4506(5) 0.0630(15) Uani d . 1 . .
    H H4A 0.2651 -0.3137 0.5068 0.076 Uiso calc R 1 . .
    H H4B 0.2805 -0.2576 0.3759 0.076 Uiso calc R 1 . .
    C C5 0.1723(3) -0.0696(6) 0.3322(4) 0.0475(12) Uani d . 1 . .
    H H5A 0.1549 -0.1350 0.2660 0.057 Uiso calc R 1 . .
    H H5B 0.2145 -0.0156 0.3071 0.057 Uiso calc R 1 . .
    C C6 0.1207(2) 0.0625(6) 0.3661(4) 0.0414(10) Uani d . 1 . .
    H H6A 0.1196 0.1499 0.3059 0.050 Uiso calc R 1 . .
    H H6B 0.0755 0.0122 0.3707 0.050 Uiso calc R 1 . .
    C C7 0.0825(2) 0.2343(6) 0.5364(4) 0.0440(11) Uani d . 1 . .
    H H7A 0.0398 0.2081 0.4967 0.053 Uiso calc R 1 . .
    H H7B 0.0912 0.3540 0.5275 0.053 Uiso calc R 1 . .
    C C8 0.0774(2) 0.1912(6) 0.6639(4) 0.0363(10) Uani d . 1 . .
    C C9 0.0488(2) 0.1931(6) 0.8520(4) 0.0399(10) Uani d . 1 . .
    C C10 0.0242(2) 0.2273(7) 0.9662(4) 0.0516(12) Uani d . 1 . .
    H H10 -0.0020 0.3225 0.9818 0.062 Uiso calc R 1 . .
    C C11 0.0401(2) 0.1160(8) 1.0527(4) 0.0560(14) Uani d . 1 . .
    H H11 0.0246 0.1358 1.1295 0.067 Uiso calc R 1 . .
    C C12 0.0792(3) -0.0283(8) 1.0299(5) 0.0572(14) Uani d . 1 . .
    H H12 0.0891 -0.1018 1.0918 0.069 Uiso calc R 1 . .
    C C13 0.1034(2) -0.0636(7) 0.9179(5) 0.0486(12) Uani d . 1 . .
    H H13 0.1288 -0.1603 0.9029 0.058 Uiso calc R 1 . .
    C C14 0.0883(2) 0.0510(7) 0.8276(4) 0.0369(10) Uani d . 1 . .
    N N1 0.13896(16) 0.1372(5) 0.4821(3) 0.0344(8) Uani d . 1 . .
    N N2 0.26097(18) 0.0110(5) 0.5943(4) 0.0487(10) Uani d . 1 . .
    H H2 0.2809 -0.0119 0.6655 0.058 Uiso calc R 1 . .
    N N3 0.1865(2) -0.1823(5) 0.4329(3) 0.0436(9) Uani d . 1 . .
    H H3 0.1635 -0.2807 0.4211 0.052 Uiso calc R 1 . .
    N N4 0.10622(17) 0.0531(5) 0.7083(3) 0.0337(8) Uani d . 1 . .
    N N5 0.04310(18) 0.2767(5) 0.7470(3) 0.0448(9) Uani d . 1 . .
    H H5 0.0211 0.3692 0.7361 0.054 Uiso calc R 1 . .
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 0.0368(2) 0.0321(3) 0.0297(3) 0.0042(2) 0.0005(2) 0.0004(2)
    Br1 0.0994(4) 0.0357(3) 0.0474(3) 0.0022(3) 0.0006(3) 0.0071(2)
    Br2 0.0459(2) 0.0481(3) 0.0509(3) -0.0080(2) -0.0043(2) 0.0023(2)
    C1 0.048(3) 0.045(3) 0.040(2) -0.013(2) 0.005(2) 0.000(2)
    C2 0.047(2) 0.063(3) 0.043(3) -0.020(2) 0.000(2) -0.001(2)
    C3 0.043(3) 0.114(5) 0.047(3) 0.021(3) 0.008(2) 0.001(3)
    C4 0.071(3) 0.072(4) 0.047(3) 0.033(3) 0.013(3) -0.002(3)
    C5 0.071(3) 0.045(3) 0.026(2) 0.005(2) -0.009(2) -0.002(2)
    C6 0.050(3) 0.039(3) 0.035(2) 0.001(2) -0.011(2) 0.000(2)
    C7 0.049(3) 0.035(3) 0.048(3) 0.010(2) 0.005(2) 0.010(2)
    C8 0.035(2) 0.037(2) 0.037(3) -0.0019(18) 0.0044(17) -0.002(2)
    C9 0.030(2) 0.046(3) 0.043(3) -0.0029(19) 0.0003(19) -0.010(2)
    C10 0.044(3) 0.064(3) 0.047(3) -0.004(2) 0.007(2) -0.013(3)
    C11 0.046(3) 0.090(4) 0.032(3) -0.007(3) 0.003(2) -0.011(3)
    C12 0.050(3) 0.087(4) 0.034(3) 0.005(3) -0.005(2) 0.005(3)
    C13 0.039(3) 0.061(3) 0.045(3) 0.010(2) 0.003(2) 0.004(2)
    C14 0.024(2) 0.050(3) 0.036(2) 0.0002(18) -0.0008(17) -0.004(2)
    N1 0.0355(19) 0.036(2) 0.0313(19) 0.0027(14) -0.0005(15) -0.0031(15)
    N2 0.0324(18) 0.081(3) 0.033(2) 0.0020(16) 0.0021(17) 0.001(2)
    N3 0.060(2) 0.034(2) 0.036(2) 0.0110(18) -0.0004(18) -0.0041(16)
    N4 0.0311(18) 0.035(2) 0.035(2) 0.0060(15) 0.0022(14) 0.0032(16)
    N5 0.045(2) 0.040(2) 0.049(2) 0.0100(16) 0.0095(17) -0.0021(18)
_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 N4 . 1.973(4) ?
    Cu1 N3 . 2.020(4) ?
    Cu1 N1 . 2.140(4) ?
    Cu1 N2 . 2.192(4) ?
    Cu1 Br1 . 2.4222(7) ?
    C1 C2 . 1.482(7) ?
    C1 N1 . 1.489(6) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 N2 . 1.487(6) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 N2 . 1.480(6) ?
    C3 C4 . 1.492(9) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 N3 . 1.494(6) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 N3 . 1.471(6) ?
    C5 C6 . 1.504(7) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 N1 . 1.479(6) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 N1 . 1.478(6) ?
    C7 C8 . 1.480(6) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 N4 . 1.331(6) ?
    C8 N5 . 1.337(5) ?
    C9 N5 . 1.361(6) ?
    C9 C14 . 1.394(7) ?
    C9 C10 . 1.400(6) ?
    C10 C11 . 1.352(7) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.401(8) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.376(8) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.397(7) ?
    C13 H13 . 0.9300 ?
    C14 N4 . 1.390(5) ?
    N2 H2 . 0.9100 ?
    N3 H3 . 0.9100 ?
    N5 H5 . 0.8600 ?
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
    N4 Cu1 N3 . . 162.57(14) ?
    N4 Cu1 N1 . . 82.38(15) ?
    N3 Cu1 N1 . . 82.96(14) ?
    N4 Cu1 N2 . . 104.71(15) ?
    N3 Cu1 N2 . . 82.83(16) ?
    N1 Cu1 N2 . . 83.24(14) ?
    N4 Cu1 Br1 . . 99.07(11) ?
    N3 Cu1 Br1 . . 92.71(11) ?
    N1 Cu1 Br1 . . 165.07(9) ?
    N2 Cu1 Br1 . . 110.49(11) ?
    C2 C1 N1 . . 113.0(4) ?
    C2 C1 H1A . . 109.0 ?
    N1 C1 H1A . . 109.0 ?
    C2 C1 H1B . . 109.0 ?
    N1 C1 H1B . . 109.0 ?
    H1A C1 H1B . . 107.8 ?
    C1 C2 N2 . . 113.0(4) ?
    C1 C2 H2A . . 109.0 ?
    N2 C2 H2A . . 109.0 ?
    C1 C2 H2B . . 109.0 ?
    N2 C2 H2B . . 109.0 ?
    H2A C2 H2B . . 107.8 ?
    N2 C3 C4 . . 111.5(4) ?
    N2 C3 H3A . . 109.3 ?
    C4 C3 H3A . . 109.3 ?
    N2 C3 H3B . . 109.3 ?
    C4 C3 H3B . . 109.3 ?
    H3A C3 H3B . . 108.0 ?
    C3 C4 N3 . . 110.9(4) ?
    C3 C4 H4A . . 109.5 ?
    N3 C4 H4A . . 109.5 ?
    C3 C4 H4B . . 109.5 ?
    N3 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 108.1 ?
    N3 C5 C6 . . 110.7(4) ?
    N3 C5 H5A . . 109.5 ?
    C6 C5 H5A . . 109.5 ?
    N3 C5 H5B . . 109.5 ?
    C6 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 108.1 ?
    N1 C6 C5 . . 110.1(4) ?
    N1 C6 H6A . . 109.6 ?
    C5 C6 H6A . . 109.6 ?
    N1 C6 H6B . . 109.6 ?
    C5 C6 H6B . . 109.6 ?
    H6A C6 H6B . . 108.2 ?
    N1 C7 C8 . . 109.4(4) ?
    N1 C7 H7A . . 109.8 ?
    C8 C7 H7A . . 109.8 ?
    N1 C7 H7B . . 109.8 ?
    C8 C7 H7B . . 109.8 ?
    H7A C7 H7B . . 108.2 ?
    N4 C8 N5 . . 111.5(4) ?
    N4 C8 C7 . . 121.8(4) ?
    N5 C8 C7 . . 126.7(4) ?
    N5 C9 C14 . . 105.5(4) ?
    N5 C9 C10 . . 132.6(4) ?
    C14 C9 C10 . . 121.9(5) ?
    C11 C10 C9 . . 117.2(5) ?
    C11 C10 H10 . . 121.4 ?
    C9 C10 H10 . . 121.4 ?
    C10 C11 C12 . . 121.8(5) ?
    C10 C11 H11 . . 119.1 ?
    C12 C11 H11 . . 119.1 ?
    C13 C12 C11 . . 121.5(5) ?
    C13 C12 H12 . . 119.3 ?
    C11 C12 H12 . . 119.3 ?
    C12 C13 C14 . . 117.6(5) ?
    C12 C13 H13 . . 121.2 ?
    C14 C13 H13 . . 121.2 ?
    N4 C14 C9 . . 108.7(4) ?
    N4 C14 C13 . . 131.3(5) ?
    C9 C14 C13 . . 120.0(4) ?
    C7 N1 C6 . . 113.3(3) ?
    C7 N1 C1 . . 111.6(4) ?
    C6 N1 C1 . . 113.2(3) ?
    C7 N1 Cu1 . . 107.7(3) ?
    C6 N1 Cu1 . . 101.9(3) ?
    C1 N1 Cu1 . . 108.4(3) ?
    C3 N2 C2 . . 114.3(4) ?
    C3 N2 Cu1 . . 107.0(3) ?
    C2 N2 Cu1 . . 101.5(3) ?
    C3 N2 H2 . . 111.2 ?
    C2 N2 H2 . . 111.2 ?
    Cu1 N2 H2 . . 111.2 ?
    C5 N3 C4 . . 114.4(4) ?
    C5 N3 Cu1 . . 112.0(3) ?
    C4 N3 Cu1 . . 104.9(3) ?
    C5 N3 H3 . . 108.4 ?
    C4 N3 H3 . . 108.4 ?
    Cu1 N3 H3 . . 108.4 ?
    C8 N4 C14 . . 105.5(4) ?
    C8 N4 Cu1 . . 113.4(3) ?
    C14 N4 Cu1 . . 141.0(4) ?
    C8 N5 C9 . . 108.7(4) ?
    C8 N5 H5 . . 125.6 ?
    C9 N5 H5 . . 125.6 ?
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
    N2 H2 Br2 . 0.91 2.64 3.395(4) 140.7
    N3 H3 Br2 4_544 0.91 2.64 3.456(4) 149.0
    N5 H5 Br2 3_455 0.86 2.58 3.269(3) 138.2
