#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/05/2230561.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_2230561
loop_
_publ_author_name
'Zhou, Fu-Lin'
'Ng, Seik Weng'
_publ_section_title
;
 Tetrakis(1H-benzimidazole-κN³)(nitrato-κO)copper(II)
 nitrate
;
_journal_coeditor_code           ZS2111
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m792
_journal_paper_doi               10.1107/S1600536811018885
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu (N O3) (C7 H6 N2)4] N O3'
_chemical_formula_moiety         'C28 H24 Cu N9 O3 +, N O3 -'
_chemical_formula_sum            'C28 H24 Cu N10 O6'
_chemical_formula_weight         660.12
_chemical_name_systematic
;
Tetrakis(1H-benzimidazole-κN³)(nitrato-κO)copper(II)
nitrate
;
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.7181(2)
_cell_length_b                   24.9338(3)
_cell_length_c                   15.1048(2)
_cell_measurement_reflns_used    5605
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.54
_cell_measurement_theta_min      2.92
_cell_volume                     5919.75(13)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Agilent Xcalibur Eos Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0109
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7285
_diffrn_reflns_theta_full        70.67
_diffrn_reflns_theta_max         70.67
_diffrn_reflns_theta_min         3.32
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.562
_exptl_absorpt_correction_T_max  0.9121
_exptl_absorpt_correction_T_min  0.8595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2712
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.313
_refine_ls_abs_structure_details 'Flack (1983), 1676 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         5038
_refine_ls_number_restraints     130
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0810P)²+2.0279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1165
_reflns_number_gt                4779
_reflns_number_total             5038
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2111.cif
_cod_data_source_block           I
_cod_database_code               2230561
_cod_database_fobs_code          2230561
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, 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'
'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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.0000 0.417817(18) 0.2500 0.03722(14) Uani d S 1 2 . .
Cu Cu2 0.5000 0.38135(2) 0.7500 0.05537(17) Uani d S 1 2 . .
O O1 -0.0129(5) 0.5148(3) 0.1902(6) 0.0616(18) Uani d PDU 0.50 1 A -1
O O2 -0.0161(7) 0.59502(16) 0.2397(10) 0.101(3) Uani d PDU 0.50 1 A -1
O O3 0.0386(5) 0.5315(3) 0.3167(6) 0.074(2) Uani d PDU 0.50 1 A -1
O O4 0.4732(5) 0.47882(18) 0.7442(8) 0.107(2) Uani d PDU 0.50 1 B -1
O O5 0.4466(6) 0.5603(3) 0.7658(10) 0.156(4) Uani d PDU 0.50 1 B -1
O O6 0.5717(4) 0.5318(3) 0.7891(6) 0.117(3) Uani d PDU 0.50 1 B -1
O O7 0.2850(7) 0.4949(5) 0.4463(6) 0.089(3) Uani d PDU 0.50 1 C -1
O O8 0.1786(3) 0.4969(4) 0.5351(5) 0.110(3) Uani d PDU 0.50 1 C -1
O O9 0.3011(5) 0.5214(4) 0.5815(5) 0.083(2) Uani d PDU 0.50 1 C -1
O O10 0.1531(11) 0.4740(12) 0.9487(14) 0.056(3) Uani d PDU 0.50 1 D -1
O O11 0.2713(2) 0.4965(11) 1.0107(14) 0.064(3) Uani d PDU 0.50 1 D -1
O O12 0.1518(13) 0.5215(12) 1.0668(14) 0.059(4) Uani d PDU 0.50 1 D -1
N N1 0.03749(15) 0.40674(10) 0.37505(15) 0.0423(5) Uani d . 1 1 A .
N N2 0.04470(17) 0.42208(11) 0.51886(16) 0.0509(6) Uani d . 1 1 A .
H H2 0.0323 0.4352 0.5714 0.061 Uiso calc R 1 1 . .
N N3 0.12264(13) 0.41851(10) 0.21267(16) 0.0436(5) Uani d . 1 1 A .
N N4 0.25856(17) 0.43865(13) 0.2204(3) 0.0744(11) Uani d . 1 1 A .
H H4 0.3059 0.4544 0.2377 0.089 Uiso calc R 1 1 . .
N N5 0.46012(19) 0.37857(12) 0.6251(2) 0.0603(7) Uani d . 1 1 B .
N N6 0.4071(2) 0.40852(14) 0.5002(2) 0.0744(9) Uani d . 1 1 B .
H H6 0.3816 0.4302 0.4626 0.089 Uiso calc R 1 1 . .
N N7 0.37999(19) 0.37880(11) 0.7923(2) 0.0598(7) Uani d . 1 1 B .
N N8 0.2594(2) 0.40803(13) 0.8488(2) 0.0708(8) Uani d . 1 1 B .
H H8 0.2231 0.4290 0.8766 0.085 Uiso calc R 1 1 . .
N N9 0.0030(5) 0.54803(13) 0.2490(8) 0.0462(9) Uani d SDU 0.50 1 A -1
N N10 0.4980(6) 0.52280(17) 0.7649(6) 0.059(3) Uani d PDU 0.50 1 B -1
N N11 0.2553(4) 0.5029(6) 0.5215(4) 0.066(3) Uani d PDU 0.50 1 C -1
N N12 0.1927(3) 0.5001(13) 1.0062(17) 0.048(2) Uani d PDU 0.50 1 D -1
C C1 0.0063(2) 0.43455(11) 0.44316(18) 0.0478(6) Uani d . 1 1 . .
H H1 -0.0372 0.4597 0.4383 0.057 Uiso calc R 1 1 A .
C C2 0.10595(12) 0.38578(8) 0.50119(11) 0.0494(6) Uani d G 1 1 . .
C C3 0.16641(15) 0.35976(10) 0.55281(9) 0.0660(9) Uani d G 1 1 A .
H H3 0.1702 0.3672 0.6130 0.079 Uiso calc R 1 1 . .
C C4 0.22118(14) 0.32267(10) 0.51443(14) 0.0723(10) Uani d G 1 1 A .
H H4A 0.2616 0.3053 0.5490 0.087 Uiso calc R 1 1 . .
C C5 0.21549(13) 0.31161(9) 0.42443(14) 0.0680(9) Uani d G 1 1 A .
H H5 0.2521 0.2868 0.3988 0.082 Uiso calc R 1 1 . .
C C6 0.15502(13) 0.33764(8) 0.37281(10) 0.0515(7) Uani d G 1 1 A .
H H6A 0.1512 0.3302 0.3126 0.062 Uiso calc R 1 1 . .
C C7 0.10025(11) 0.37472(7) 0.41119(11) 0.0428(6) Uani d G 1 1 A .
C C8 0.18048(17) 0.44833(12) 0.2533(3) 0.0563(7) Uani d . 1 1 . .
H H8A 0.1687 0.4726 0.2983 0.068 Uiso calc R 1 1 A .
C C9 0.16669(11) 0.38703(9) 0.15231(13) 0.0509(7) Uani d G 1 1 . .
C C10 0.13867(13) 0.34785(10) 0.09369(15) 0.0656(9) Uani d G 1 1 A .
H H10 0.0813 0.3389 0.0914 0.079 Uiso calc R 1 1 . .
C C11 0.1964(2) 0.32205(10) 0.03854(15) 0.0909(16) Uani d G 1 1 A .
H H11 0.1777 0.2958 -0.0007 0.109 Uiso calc R 1 1 . .
C C12 0.28222(19) 0.33543(13) 0.04201(19) 0.0989(18) Uani d G 1 1 A .
H H12 0.3209 0.3182 0.0051 0.119 Uiso calc R 1 1 . .
C C13 0.31024(11) 0.37460(13) 0.1006(2) 0.109(2) Uani d G 1 1 A .
H H13 0.3676 0.3836 0.1029 0.131 Uiso calc R 1 1 . .
C C14 0.25248(13) 0.40040(10) 0.15578(17) 0.0682(10) Uani d G 1 1 A .
C C15 0.4189(3) 0.41740(16) 0.5867(3) 0.0720(10) Uani d . 1 1 . .
H H15 0.3998 0.4479 0.6161 0.086 Uiso calc R 1 1 B .
C C16 0.44165(15) 0.36015(8) 0.48107(15) 0.0637(8) Uani d G 1 1 . .
C C17 0.44827(18) 0.32937(11) 0.40466(12) 0.0818(12) Uani d G 1 1 B .
H H17 0.4260 0.3420 0.3516 0.098 Uiso calc R 1 1 . .
C C18 0.48821(18) 0.27966(11) 0.40755(14) 0.0836(12) Uani d G 1 1 B .
H H18 0.4926 0.2591 0.3564 0.100 Uiso calc R 1 1 . .
C C19 0.52152(16) 0.26073(8) 0.48686(18) 0.0764(11) Uani d G 1 1 B .
H H19 0.5482 0.2275 0.4888 0.092 Uiso calc R 1 1 . .
C C20 0.51490(15) 0.29151(8) 0.56328(14) 0.0638(9) Uani d G 1 1 B .
H H20 0.5372 0.2788 0.6163 0.077 Uiso calc R 1 1 . .
C C21 0.47496(14) 0.34122(8) 0.56039(12) 0.0555(7) Uani d G 1 1 B .
C C22 0.3423(3) 0.41754(16) 0.8371(3) 0.0691(9) Uani d . 1 1 . .
H H22 0.3702 0.4479 0.8581 0.083 Uiso calc R 1 1 B .
C C23 0.24100(14) 0.36003(8) 0.80981(14) 0.0602(8) Uani d G 1 1 . .
C C24 0.16767(11) 0.32924(11) 0.80189(16) 0.0787(12) Uani d G 1 1 B .
H H24 0.1166 0.3415 0.8255 0.094 Uiso calc R 1 1 . .
C C25 0.17062(13) 0.28005(11) 0.75867(18) 0.0788(10) Uani d G 1 1 B .
H H25 0.1216 0.2595 0.7534 0.095 Uiso calc R 1 1 . .
C C26 0.24690(16) 0.26166(8) 0.72338(16) 0.0724(10) Uani d G 1 1 B .
H H26 0.2489 0.2288 0.6945 0.087 Uiso calc R 1 1 . .
C C27 0.32023(12) 0.29245(8) 0.73130(14) 0.0616(8) Uani d G 1 1 B .
H H27 0.3713 0.2801 0.7077 0.074 Uiso calc R 1 1 . .
C C28 0.31728(11) 0.34163(8) 0.77451(14) 0.0550(7) Uani d G 1 1 B .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Cu1 N1 4 . 164.10(14) ?
N1 Cu1 N3 4 . 91.08(10) ?
N1 Cu1 N3 . . 89.06(10) ?
N1 Cu1 N3 4 4 89.06(10) ?
N1 Cu1 N3 . 4 91.08(10) ?
N3 Cu1 N3 . 4 179.02(14) ?
N1 Cu1 O1 4 . 77.06(17) ?
N1 Cu1 O1 . . 118.83(17) ?
N3 Cu1 O1 . . 88.23(19) ?
N3 Cu1 O1 4 . 90.9(2) ?
N5 Cu2 N5 . 4_656 176.00(17) ?
N5 Cu2 N7 . 4_656 89.60(13) ?
N5 Cu2 N7 4_656 4_656 90.27(13) ?
N5 Cu2 N7 . . 90.27(13) ?
N5 Cu2 N7 4_656 . 89.60(13) ?
N7 Cu2 N7 4_656 . 176.34(17) ?
N5 Cu2 O4 . . 87.0(3) ?
N5 Cu2 O4 4_656 . 97.0(3) ?
N7 Cu2 O4 4_656 . 100.5(2) ?
N7 Cu2 O4 . . 83.2(2) ?
N9 O1 Cu1 . . 111.0(5) ?
N10 O4 Cu2 . . 146.3(6) ?
C1 N1 C7 . . 105.0(2) ?
C1 N1 Cu1 . . 123.3(2) ?
C7 N1 Cu1 . . 131.62(17) ?
C1 N2 C2 . . 108.1(2) ?
C1 N2 H2 . . 125.9 ?
C2 N2 H2 . . 125.9 ?
C8 N3 C9 . . 106.2(2) ?
C8 N3 Cu1 . . 122.2(2) ?
C9 N3 Cu1 . . 131.17(17) ?
C8 N4 C14 . . 109.0(3) ?
C8 N4 H4 . . 125.5 ?
C14 N4 H4 . . 125.5 ?
C15 N5 C21 . . 105.8(3) ?
C15 N5 Cu2 . . 123.6(3) ?
C21 N5 Cu2 . . 130.3(2) ?
C15 N6 C16 . . 107.5(3) ?
C15 N6 H6 . . 126.3 ?
C16 N6 H6 . . 126.3 ?
C22 N7 C28 . . 105.7(3) ?
C22 N7 Cu2 . . 124.5(3) ?
C28 N7 Cu2 . . 129.45(19) ?
C22 N8 C23 . . 107.8(3) ?
C22 N8 H8 . . 126.1 ?
C23 N8 H8 . . 126.1 ?
O2 N9 O3 . . 121.8(8) ?
O2 N9 O1 . . 120.7(9) ?
O3 N9 O1 . . 117.5(5) ?
O4 N10 O5 . . 118.7(9) ?
O4 N10 O6 . . 123.0(7) ?
O5 N10 O6 . . 118.2(7) ?
O8 N11 O7 . . 120.0(7) ?
O8 N11 O9 . . 119.3(7) ?
O7 N11 O9 . . 120.4(7) ?
O11 N12 O12 . . 120.5(10) ?
O11 N12 O10 . . 119.7(10) ?
O12 N12 O10 . . 118.6(6) ?
N2 C1 N1 . . 112.0(3) ?
N2 C1 H1 . . 124.0 ?
N1 C1 H1 . . 124.0 ?
N2 C2 C3 . . 133.68(17) ?
N2 C2 C7 . . 106.31(17) ?
C3 C2 C7 . . 120.0 ?
C2 C3 C4 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C3 C4 C5 . . 120.0 ?
C3 C4 H4A . . 120.0 ?
C5 C4 H4A . . 120.0 ?
C4 C5 C6 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C7 C6 C5 . . 120.0 ?
C7 C6 H6A . . 120.0 ?
C5 C6 H6A . . 120.0 ?
N1 C7 C6 . . 131.44(15) ?
N1 C7 C2 . . 108.53(15) ?
C6 C7 C2 . . 120.0 ?
N3 C8 N4 . . 110.7(3) ?
N3 C8 H8A . . 124.6 ?
N4 C8 H8A . . 124.6 ?
N3 C9 C10 . . 131.12(17) ?
N3 C9 C14 . . 108.88(17) ?
C10 C9 C14 . . 120.0 ?
C9 C10 C11 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C10 C11 C12 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C13 C12 C11 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
N4 C14 C13 . . 134.80(19) ?
N4 C14 C9 . . 105.18(19) ?
C13 C14 C9 . . 120.0 ?
N5 C15 N6 . . 112.4(4) ?
N5 C15 H15 . . 123.8 ?
N6 C15 H15 . . 123.8 ?
N6 C16 C17 . . 134.4(2) ?
N6 C16 C21 . . 105.6(2) ?
C17 C16 C21 . . 120.0 ?
C16 C17 C18 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
C18 C17 H17 . . 120.0 ?
C19 C18 C17 . . 120.0 ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C20 C19 C18 . . 120.0 ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C19 C20 C21 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C21 C20 H20 . . 120.0 ?
N5 C21 C20 . . 131.35(19) ?
N5 C21 C16 . . 108.65(19) ?
C20 C21 C16 . . 120.0 ?
N7 C22 N8 . . 112.0(4) ?
N7 C22 H22 . . 124.0 ?
N8 C22 H22 . . 124.0 ?
N8 C23 C24 . . 134.2(2) ?
N8 C23 C28 . . 105.8(2) ?
C24 C23 C28 . . 120.0 ?
C23 C24 C25 . . 120.0 ?
C23 C24 H24 . . 120.0 ?
C25 C24 H24 . . 120.0 ?
C26 C25 C24 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
C24 C25 H25 . . 120.0 ?
C27 C26 C25 . . 120.0 ?
C27 C26 H26 . . 120.0 ?
C25 C26 H26 . . 120.0 ?
C26 C27 C28 . . 120.0 ?
C26 C27 H27 . . 120.0 ?
C28 C27 H27 . . 120.0 ?
N7 C28 C27 . . 131.33(18) ?
N7 C28 C23 . . 108.66(18) ?
C27 C28 C23 . . 120.0 ?
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 4 1.998(2) ?
Cu1 N1 . 1.998(2) ?
Cu1 N3 . 2.008(2) ?
Cu1 N3 4 2.008(2) ?
Cu1 O1 . 2.590(7) ?
Cu2 N5 . 1.989(3) ?
Cu2 N5 4_656 1.989(3) ?
Cu2 N7 4_656 1.993(3) ?
Cu2 N7 . 1.993(3) ?
Cu2 O4 . 2.468(5) ?
O1 N9 . 1.240(7) ?
O2 N9 . 1.218(5) ?
O3 N9 . 1.236(9) ?
O4 N10 . 1.205(6) ?
O5 N10 . 1.234(7) ?
O6 N10 . 1.237(8) ?
O7 N11 . 1.244(8) ?
O8 N11 . 1.231(7) ?
O9 N11 . 1.246(8) ?
O10 N12 . 1.250(8) ?
O11 N12 . 1.240(6) ?
O12 N12 . 1.239(8) ?
N1 C1 . 1.334(4) ?
N1 C7 . 1.382(3) ?
N2 C1 . 1.330(4) ?
N2 C2 . 1.348(3) ?
N2 H2 . 0.8800 ?
N3 C8 . 1.325(4) ?
N3 C9 . 1.388(3) ?
N4 C8 . 1.346(4) ?
N4 C14 . 1.368(4) ?
N4 H4 . 0.8800 ?
N5 C15 . 1.301(5) ?
N5 C21 . 1.370(3) ?
N6 C15 . 1.338(6) ?
N6 C16 . 1.354(4) ?
N6 H6 . 0.8800 ?
N7 C22 . 1.320(5) ?
N7 C28 . 1.379(3) ?
N8 C22 . 1.337(5) ?
N8 C23 . 1.365(4) ?
N8 H8 . 0.8800 ?
C1 H1 . 0.9300 ?
C2 C3 . 1.3900 ?
C2 C7 . 1.3900 ?
C3 C4 . 1.3900 ?
C3 H3 . 0.9300 ?
C4 C5 . 1.3900 ?
C4 H4A . 0.9300 ?
C5 C6 . 1.3900 ?
C5 H5 . 0.9300 ?
C6 C7 . 1.3900 ?
C6 H6A . 0.9300 ?
C8 H8A . 0.9300 ?
C9 C10 . 1.3900 ?
C9 C14 . 1.3900 ?
C10 C11 . 1.3900 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.3900 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.3900 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.3900 ?
C13 H13 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.3900 ?
C16 C21 . 1.3900 ?
C17 C18 . 1.3900 ?
C17 H17 . 0.9300 ?
C18 C19 . 1.3900 ?
C18 H18 . 0.9300 ?
C19 C20 . 1.3900 ?
C19 H19 . 0.9300 ?
C20 C21 . 1.3900 ?
C20 H20 . 0.9300 ?
C22 H22 . 0.9300 ?
C23 C24 . 1.3900 ?
C23 C28 . 1.3900 ?
C24 C25 . 1.3900 ?
C24 H24 . 0.9300 ?
C25 C26 . 1.3900 ?
C25 H25 . 0.9300 ?
C26 C27 . 1.3900 ?
C26 H26 . 0.9300 ?
C27 C28 . 1.3900 ?
C27 H27 . 0.9300 ?
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
N2 H2 O1 2_565 0.88 2.21 3.069(9) 167 yes
N2 H2 O3 3_566 0.88 1.89 2.742(9) 164 yes
N4 H4 O5 3_566 0.88 2.24 2.964(9) 139 yes
N4 H4 O6 2_664 0.88 2.10 2.955(7) 163 yes
N6 H6 O7 . 0.88 2.23 2.998(14) 146 yes
N8 H8 O10 . 0.88 1.91 2.79(2) 173 yes
N8 H8 O12 3_567 0.88 1.87 2.75(3) 175 yes
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
N1 Cu1 O1 N9 4 . . . 177.7(5) ?
N1 Cu1 O1 N9 . . . . -2.8(5) ?
N3 Cu1 O1 N9 . . . . -90.8(4) ?
N3 Cu1 O1 N9 4 . . . 88.9(4) ?
N5 Cu2 O4 N10 . . . . -139.8(18) ?
N5 Cu2 O4 N10 4_656 . . . 40.8(18) ?
N7 Cu2 O4 N10 4_656 . . . -50.8(18) ?
N7 Cu2 O4 N10 . . . . 129.6(18) ?
N1 Cu1 N1 C1 4 . . . -136.0(2) ?
N3 Cu1 N1 C1 . . . . 133.4(2) ?
N3 Cu1 N1 C1 4 . . . -45.7(2) ?
O1 Cu1 N1 C1 . . . . 45.9(3) ?
N1 Cu1 N1 C7 4 . . . 49.0(2) ?
N3 Cu1 N1 C7 . . . . -41.7(2) ?
N3 Cu1 N1 C7 4 . . . 139.3(2) ?
O1 Cu1 N1 C7 . . . . -129.1(3) ?
N1 Cu1 N3 C8 4 . . . 146.8(2) ?
N1 Cu1 N3 C8 . . . . -49.1(2) ?
O1 Cu1 N3 C8 . . . . 69.8(3) ?
N1 Cu1 N3 C9 4 . . . -41.4(2) ?
N1 Cu1 N3 C9 . . . . 122.7(2) ?
O1 Cu1 N3 C9 . . . . -118.4(3) ?
N7 Cu2 N5 C15 4_656 . . . -115.3(3) ?
N7 Cu2 N5 C15 . . . . 68.3(3) ?
O4 Cu2 N5 C15 . . . . -14.8(4) ?
N7 Cu2 N5 C21 4_656 . . . 57.7(3) ?
N7 Cu2 N5 C21 . . . . -118.6(3) ?
O4 Cu2 N5 C21 . . . . 158.2(4) ?
N5 Cu2 N7 C22 . . . . -116.5(3) ?
N5 Cu2 N7 C22 4_656 . . . 67.5(3) ?
O4 Cu2 N7 C22 . . . . -29.6(4) ?
N5 Cu2 N7 C28 . . . . 55.6(3) ?
N5 Cu2 N7 C28 4_656 . . . -120.4(3) ?
O4 Cu2 N7 C28 . . . . 142.5(4) ?
Cu1 O1 N9 O2 . . . . -165.0(7) ?
Cu1 O1 N9 O3 . . . . 15.0(7) ?
Cu2 O4 N10 O5 . . . . -159.8(14) ?
Cu2 O4 N10 O6 . . . . 17(2) ?
C2 N2 C1 N1 . . . . 2.0(3) ?
C7 N1 C1 N2 . . . . -0.2(3) ?
Cu1 N1 C1 N2 . . . . -176.4(2) ?
C1 N2 C2 C3 . . . . 178.3(2) ?
C1 N2 C2 C7 . . . . -2.8(3) ?
N2 C2 C3 C4 . . . . 178.8(3) ?
C7 C2 C3 C4 . . . . 0.0 ?
C2 C3 C4 C5 . . . . 0.0 ?
C3 C4 C5 C6 . . . . 0.0 ?
C4 C5 C6 C7 . . . . 0.0 ?
C1 N1 C7 C6 . . . . -179.5(2) ?
Cu1 N1 C7 C6 . . . . -3.8(3) ?
C1 N1 C7 C2 . . . . -1.6(2) ?
Cu1 N1 C7 C2 . . . . 174.14(17) ?
C5 C6 C7 N1 . . . . 177.7(2) ?
C5 C6 C7 C2 . . . . 0.0 ?
N2 C2 C7 N1 . . . . 2.7(2) ?
C3 C2 C7 N1 . . . . -178.2(2) ?
N2 C2 C7 C6 . . . . -179.1(2) ?
C3 C2 C7 C6 . . . . 0.0 ?
C9 N3 C8 N4 . . . . 1.7(4) ?
Cu1 N3 C8 N4 . . . . 175.3(2) ?
C14 N4 C8 N3 . . . . -0.6(4) ?
C8 N3 C9 C10 . . . . 178.5(2) ?
Cu1 N3 C9 C10 . . . . 5.7(3) ?
C8 N3 C9 C14 . . . . -2.2(3) ?
Cu1 N3 C9 C14 . . . . -174.97(16) ?
N3 C9 C10 C11 . . . . 179.3(2) ?
C14 C9 C10 C11 . . . . 0.0 ?
C9 C10 C11 C12 . . . . 0.0 ?
C10 C11 C12 C13 . . . . 0.0 ?
C11 C12 C13 C14 . . . . 0.0 ?
C8 N4 C14 C13 . . . . -179.2(2) ?
C8 N4 C14 C9 . . . . -0.8(3) ?
C12 C13 C14 N4 . . . . 178.3(3) ?
C12 C13 C14 C9 . . . . 0.0 ?
N3 C9 C14 N4 . . . . 1.8(2) ?
C10 C9 C14 N4 . . . . -178.7(2) ?
N3 C9 C14 C13 . . . . -179.4(2) ?
C10 C9 C14 C13 . . . . 0.0 ?
C21 N5 C15 N6 . . . . -1.3(5) ?
Cu2 N5 C15 N6 . . . . 173.2(3) ?
C16 N6 C15 N5 . . . . 1.2(5) ?
C15 N6 C16 C17 . . . . 178.9(3) ?
C15 N6 C16 C21 . . . . -0.5(4) ?
N6 C16 C17 C18 . . . . -179.4(3) ?
C21 C16 C17 C18 . . . . 0.0 ?
C16 C17 C18 C19 . . . . 0.0 ?
C17 C18 C19 C20 . . . . 0.0 ?
C18 C19 C20 C21 . . . . 0.0 ?
C15 N5 C21 C20 . . . . -178.8(3) ?
Cu2 N5 C21 C20 . . . . 7.2(4) ?
C15 N5 C21 C16 . . . . 0.9(3) ?
Cu2 N5 C21 C16 . . . . -173.1(2) ?
C19 C20 C21 N5 . . . . 179.8(3) ?
C19 C20 C21 C16 . . . . 0.0 ?
N6 C16 C21 N5 . . . . -0.3(3) ?
C17 C16 C21 N5 . . . . -179.8(2) ?
N6 C16 C21 C20 . . . . 179.6(2) ?
C17 C16 C21 C20 . . . . 0.0 ?
C28 N7 C22 N8 . . . . -0.5(4) ?
Cu2 N7 C22 N8 . . . . 173.2(3) ?
C23 N8 C22 N7 . . . . 0.3(4) ?
C22 N8 C23 C24 . . . . 178.5(2) ?
C22 N8 C23 C28 . . . . 0.0(3) ?
N8 C23 C24 C25 . . . . -178.3(3) ?
C28 C23 C24 C25 . . . . 0.0 ?
C23 C24 C25 C26 . . . . 0.0 ?
C24 C25 C26 C27 . . . . 0.0 ?
C25 C26 C27 C28 . . . . 0.0 ?
C22 N7 C28 C27 . . . . -178.4(2) ?
Cu2 N7 C28 C27 . . . . 8.3(4) ?
C22 N7 C28 C23 . . . . 0.5(3) ?
Cu2 N7 C28 C23 . . . . -172.7(2) ?
C26 C27 C28 N7 . . . . 178.8(3) ?
C26 C27 C28 C23 . . . . 0.0 ?
N8 C23 C28 N7 . . . . -0.3(2) ?
C24 C23 C28 N7 . . . . -179.1(2) ?
N8 C23 C28 C27 . . . . 178.7(2) ?
C24 C23 C28 C27 . . . . 0.0 ?
