#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/28/2232840.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_2232840
loop_
_publ_author_name
'Luo, Yuan-yuan'
_publ_section_title
;
 Di-μ-azido-κ⁴N:N-bis{aqua[bis(1H-benzimidazol-2-ylmethyl)amine]copper(II)}
 dinitrate
;
_journal_coeditor_code           LH5362
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1703
_journal_page_last               m1704
_journal_paper_doi               10.1107/S1600536811045909
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu2 (N3)2 (C16 H15 N5)2 (H2 O)2] (N O3)2'
_chemical_formula_moiety         'C32 H34 Cu2 N16 O2 2+, 2(N O3 -)'
_chemical_formula_sum            'C32 H34 Cu2 N18 O8'
_chemical_formula_weight         925.85
_chemical_name_systematic
;
Di-μ-azido-κ⁴N:N-bis{aqua[bis(1H-
benzimidazol-2-ylmethyl)amine]copper(II)} dinitrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 112.0460(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.1435(10)
_cell_length_b                   14.1942(12)
_cell_length_c                   12.6567(11)
_cell_measurement_reflns_used    1625
_cell_measurement_temperature    289(2)
_cell_measurement_theta_max      19.69
_cell_measurement_theta_min      2.25
_cell_volume                     1855.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      289(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '0.3° wide ω exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed Siemens Mo tube'
_diffrn_radiation_type           'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_sigmaI/netI    0.0658
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13705
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    1.225
_exptl_absorpt_correction_T_max  0.8873
_exptl_absorpt_correction_T_min  0.7918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.485
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0706
_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)+(0.0796P)²+1.2353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1714
_reflns_number_gt                2307
_reflns_number_total             3269
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5362.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2232840
_cod_database_fobs_code          2232840
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cu Cu1 0.11004(7) 0.50588(5) 0.14302(5) 0.0427(3) Uani d . 1 1
C C1 0.0889(6) 0.3158(4) 0.2197(5) 0.0482(15) Uani d . 1 1
H H1A 0.0034 0.2917 0.1748 0.058 Uiso calc R 1 1
H H1B 0.1275 0.2757 0.2859 0.058 Uiso calc R 1 1
C C2 0.1714(5) 0.3173(4) 0.1500(4) 0.0393(13) Uani d . 1 1
C C3 0.2744(5) 0.3736(4) 0.0492(4) 0.0376(13) Uani d . 1 1
C C4 0.3333(5) 0.4286(4) -0.0078(4) 0.0438(14) Uani d . 1 1
H H4 0.3273 0.4939 -0.0082 0.053 Uiso calc R 1 1
C C5 0.4012(6) 0.3829(5) -0.0638(5) 0.0514(16) Uani d . 1 1
H H5 0.4397 0.4181 -0.1044 0.062 Uiso calc R 1 1
C C6 0.4134(6) 0.2848(5) -0.0609(5) 0.0556(17) Uani d . 1 1
H H6 0.4618 0.2562 -0.0979 0.067 Uiso calc R 1 1
C C7 0.3557(6) 0.2304(4) -0.0050(5) 0.0497(15) Uani d . 1 1
H H7 0.3623 0.1651 -0.0045 0.060 Uiso calc R 1 1
C C8 0.2877(5) 0.2751(4) 0.0506(4) 0.0396(13) Uani d . 1 1
C C9 -0.0342(6) 0.4390(4) 0.2785(5) 0.0486(15) Uani d . 1 1
H H9A -0.0233 0.4218 0.3557 0.058 Uiso calc R 1 1
H H9B -0.1107 0.4076 0.2260 0.058 Uiso calc R 1 1
C C10 -0.0471(5) 0.5443(4) 0.2630(4) 0.0422(13) Uani d . 1 1
C C11 -0.0245(5) 0.6839(4) 0.2032(4) 0.0352(12) Uani d . 1 1
C C12 0.0091(5) 0.7629(4) 0.1561(4) 0.0425(14) Uani d . 1 1
H H12 0.0600 0.7585 0.1125 0.051 Uiso calc R 1 1
C C13 -0.0366(5) 0.8486(4) 0.1771(5) 0.0462(14) Uani d . 1 1
H H13 -0.0172 0.9028 0.1455 0.055 Uiso calc R 1 1
C C14 -0.1105(6) 0.8561(5) 0.2438(5) 0.0525(16) Uani d . 1 1
H H14 -0.1379 0.9153 0.2568 0.063 Uiso calc R 1 1
C C15 -0.1442(5) 0.7788(4) 0.2909(5) 0.0479(15) Uani d . 1 1
H H15 -0.1941 0.7840 0.3353 0.058 Uiso calc R 1 1
C C16 -0.0999(5) 0.6915(4) 0.2692(4) 0.0415(14) Uani d . 1 1
N N1 0.0799(5) 0.4121(4) 0.2551(4) 0.0534(13) Uani d D 1 1
H H1C 0.144(4) 0.429(5) 0.315(3) 0.064 Uiso d D 1 1
N N2 0.2008(4) 0.3982(3) 0.1129(4) 0.0413(11) Uani d . 1 1
N N3 0.2202(5) 0.2429(3) 0.1156(4) 0.0429(11) Uani d D 1 1
H H3A 0.214(6) 0.1862(17) 0.129(5) 0.051 Uiso d D 1 1
N N4 0.0095(4) 0.5898(3) 0.2030(3) 0.0363(10) Uani d . 1 1
N N5 -0.1132(4) 0.6021(3) 0.3045(4) 0.0425(11) Uani d D 1 1
H H5A -0.150(5) 0.586(4) 0.350(4) 0.051 Uiso d D 1 1
N N6 0.1104(5) 0.5834(4) 0.0151(4) 0.0523(13) Uani d . 1 1
N N7 0.1896(6) 0.6430(4) 0.0265(4) 0.0521(13) Uani d . 1 1
N N8 0.2602(7) 0.7025(5) 0.0279(6) 0.091(2) Uani d . 1 1
N N9 0.3202(6) 0.4259(4) 0.5493(5) 0.0575(14) Uani d . 1 1
O O1 0.2058(5) 0.4516(4) 0.5211(4) 0.0719(13) Uani d . 1 1
O O2 0.3693(5) 0.4251(4) 0.4759(4) 0.0842(16) Uani d . 1 1
O O3 0.3826(5) 0.4022(4) 0.6480(4) 0.0759(14) Uani d . 1 1
O O4 0.3352(5) 0.5660(4) 0.3111(4) 0.0681(13) Uani d D 1 1
H H4A 0.335(6) 0.541(6) 0.371(4) 0.102 Uiso d D 1 1
H H4B 0.410(3) 0.568(6) 0.313(6) 0.102 Uiso d D 1 1
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'
O O 0.0106 0.0060 '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'
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
N2 Cu1 N6 . 96.73(19)
N2 Cu1 N4 . 163.95(17)
N6 Cu1 N4 . 99.01(19)
N2 Cu1 N1 . 81.88(19)
N6 Cu1 N1 . 169.2(2)
N4 Cu1 N1 . 82.07(19)
N2 Cu1 O4 . 90.27(17)
N6 Cu1 O4 . 100.4(2)
N4 Cu1 O4 . 90.01(16)
N1 Cu1 O4 . 90.29(18)
N2 Cu1 N6 3_565 83.48(17)
N6 Cu1 N6 3_565 86.4(2)
N4 Cu1 N6 3_565 94.31(16)
N1 Cu1 N6 3_565 82.82(18)
O4 Cu1 N6 3_565 171.27(14)
N1 C1 C2 . 107.3(5)
N1 C1 H1A . 110.3
C2 C1 H1A . 110.3
N1 C1 H1B . 110.3
C2 C1 H1B . 110.3
H1A C1 H1B . 108.5
N2 C2 N3 . 112.6(5)
N2 C2 C1 . 120.6(5)
N3 C2 C1 . 126.8(5)
C4 C3 N2 . 131.1(5)
C4 C3 C8 . 119.9(5)
N2 C3 C8 . 109.0(5)
C5 C4 C3 . 117.5(6)
C5 C4 H4 . 121.2
C3 C4 H4 . 121.2
C4 C5 C6 . 121.5(6)
C4 C5 H5 . 119.3
C6 C5 H5 . 119.3
C7 C6 C5 . 121.2(6)
C7 C6 H6 . 119.4
C5 C6 H6 . 119.4
C6 C7 C8 . 117.7(6)
C6 C7 H7 . 121.1
C8 C7 H7 . 121.1
C7 C8 N3 . 133.0(6)
C7 C8 C3 . 122.1(5)
N3 C8 C3 . 104.9(5)
N1 C9 C10 . 106.3(4)
N1 C9 H9A . 110.5
C10 C9 H9A . 110.5
N1 C9 H9B . 110.5
C10 C9 H9B . 110.5
H9A C9 H9B . 108.7
N4 C10 N5 . 112.2(5)
N4 C10 C9 . 121.1(5)
N5 C10 C9 . 126.7(5)
C12 C11 N4 . 131.3(5)
C12 C11 C16 . 121.0(5)
N4 C11 C16 . 107.6(5)
C13 C12 C11 . 116.8(5)
C13 C12 H12 . 121.6
C11 C12 H12 . 121.6
C12 C13 C14 . 122.0(6)
C12 C13 H13 . 119.0
C14 C13 H13 . 119.0
C15 C14 C13 . 121.8(6)
C15 C14 H14 . 119.1
C13 C14 H14 . 119.1
C14 C15 C16 . 116.8(5)
C14 C15 H15 . 121.6
C16 C15 H15 . 121.6
N5 C16 C11 . 106.6(5)
N5 C16 C15 . 131.8(5)
C11 C16 C15 . 121.6(5)
C1 N1 C9 . 118.3(5)
C1 N1 Cu1 . 110.3(3)
C9 N1 Cu1 . 110.5(4)
C1 N1 H1C . 114(5)
C9 N1 H1C . 104(4)
Cu1 N1 H1C . 98(4)
C2 N2 C3 . 105.3(4)
C2 N2 Cu1 . 113.3(3)
C3 N2 Cu1 . 140.5(4)
C2 N3 C8 . 108.2(4)
C2 N3 H3A . 128(4)
C8 N3 H3A . 123(4)
C10 N4 C11 . 106.3(4)
C10 N4 Cu1 . 112.8(4)
C11 N4 Cu1 . 140.9(3)
C10 N5 C16 . 107.3(4)
C10 N5 H5A . 125(4)
C16 N5 H5A . 127(4)
N7 N6 Cu1 . 122.0(4)
N8 N7 N6 . 174.1(7)
O3 N9 O2 . 121.2(6)
O3 N9 O1 . 120.0(5)
O2 N9 O1 . 118.7(6)
Cu1 O4 H4A . 105(5)
Cu1 O4 H4B . 131(5)
H4A O4 H4B . 109(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 N2 . 1.947(4)
Cu1 N6 . 1.959(5)
Cu1 N4 . 1.972(4)
Cu1 N1 . 2.062(5)
Cu1 O4 . 2.747(5)
Cu1 N6 3_565 2.821(6)
C1 N1 . 1.454(8)
C1 C2 . 1.494(7)
C1 H1A . 0.9700
C1 H1B . 0.9700
C2 N2 . 1.327(7)
C2 N3 . 1.333(7)
C3 C4 . 1.384(7)
C3 N2 . 1.394(6)
C3 C8 . 1.405(8)
C4 C5 . 1.377(7)
C4 H4 . 0.9300
C5 C6 . 1.399(9)
C5 H5 . 0.9300
C6 C7 . 1.360(8)
C6 H6 . 0.9300
C7 C8 . 1.367(8)
C7 H7 . 0.9300
C8 N3 . 1.385(7)
C9 N1 . 1.460(7)
C9 C10 . 1.507(8)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 N4 . 1.323(6)
C10 N5 . 1.336(7)
C11 C12 . 1.386(7)
C11 N4 . 1.388(6)
C11 C16 . 1.394(7)
C12 C13 . 1.381(8)
C12 H12 . 0.9300
C13 C14 . 1.388(8)
C13 H13 . 0.9300
C14 C15 . 1.367(8)
C14 H14 . 0.9300
C15 C16 . 1.398(8)
C15 H15 . 0.9300
C16 N5 . 1.372(7)
N1 H1C . 0.86(2)
N3 H3A . 0.83(2)
N5 H5A . 0.86(2)
N6 N7 . 1.191(7)
N7 N8 . 1.150(8)
N9 O3 . 1.228(6)
N9 O2 . 1.243(6)
N9 O1 . 1.243(7)
O4 H4A . 0.84(2)
O4 H4B . 0.83(2)
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
N1 H1C O1 . 0.86(2) 2.45(4) 3.173(7) 142(5) y
N1 H1C O2 . 0.86(2) 2.57(3) 3.388(8) 159(6) y
N3 H3A O4 2_545 0.83(2) 2.02(3) 2.825(7) 162(6) y
N5 H5A O1 3_566 0.86(2) 2.02(2) 2.868(6) 171(5) y
O4 H4A O2 . 0.84(2) 2.06(5) 2.810(7) 149(8) y
O4 H4B O3 3_666 0.83(2) 2.21(3) 3.022(7) 166(8) y
C1 H1B N8 2_545 0.97 2.45 3.404(9) 169.1 y
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
N1 C1 C2 N2 . -12.8(7)
N1 C1 C2 N3 . 169.1(5)
N2 C3 C4 C5 . 179.7(5)
C8 C3 C4 C5 . 1.4(8)
C3 C4 C5 C6 . -1.7(9)
C4 C5 C6 C7 . 1.7(9)
C5 C6 C7 C8 . -1.4(9)
C6 C7 C8 N3 . -179.0(6)
C6 C7 C8 C3 . 1.2(8)
C4 C3 C8 C7 . -1.3(8)
N2 C3 C8 C7 . -179.9(5)
C4 C3 C8 N3 . 178.9(5)
N2 C3 C8 N3 . 0.3(6)
N1 C9 C10 N4 . 20.0(7)
N1 C9 C10 N5 . -160.1(5)
N4 C11 C12 C13 . -176.7(5)
C16 C11 C12 C13 . -0.5(8)
C11 C12 C13 C14 . 1.2(8)
C12 C13 C14 C15 . -1.2(9)
C13 C14 C15 C16 . 0.3(9)
C12 C11 C16 N5 . -178.7(5)
N4 C11 C16 N5 . -1.8(6)
C12 C11 C16 C15 . -0.2(8)
N4 C11 C16 C15 . 176.7(5)
C14 C15 C16 N5 . 178.4(6)
C14 C15 C16 C11 . 0.3(8)
C2 C1 N1 C9 . 153.2(5)
C2 C1 N1 Cu1 . 24.7(6)
C10 C9 N1 C1 . -156.2(5)
C10 C9 N1 Cu1 . -27.8(5)
N2 Cu1 N1 C1 . -23.7(4)
N6 Cu1 N1 C1 . 59.6(12)
N4 Cu1 N1 C1 . 156.1(4)
O4 Cu1 N1 C1 . -113.9(4)
N6 Cu1 N1 C1 3_565 60.7(4)
N2 Cu1 N1 C9 . -156.3(4)
N6 Cu1 N1 C9 . -73.0(12)
N4 Cu1 N1 C9 . 23.4(4)
O4 Cu1 N1 C9 . 113.4(4)
N6 Cu1 N1 C9 3_565 -71.9(4)
N3 C2 N2 C3 . 0.1(6)
C1 C2 N2 C3 . -178.3(5)
N3 C2 N2 Cu1 . 171.5(4)
C1 C2 N2 Cu1 . -6.9(7)
C4 C3 N2 C2 . -178.6(6)
C8 C3 N2 C2 . -0.2(6)
C4 C3 N2 Cu1 . 13.8(10)
C8 C3 N2 Cu1 . -167.8(4)
N6 Cu1 N2 C2 . -152.5(4)
N4 Cu1 N2 C2 . 16.0(9)
N1 Cu1 N2 C2 . 16.7(4)
O4 Cu1 N2 C2 . 107.0(4)
N6 Cu1 N2 C2 3_565 -66.9(4)
N6 Cu1 N2 C3 . 14.4(6)
N4 Cu1 N2 C3 . -177.1(6)
N1 Cu1 N2 C3 . -176.4(6)
O4 Cu1 N2 C3 . -86.1(6)
N6 Cu1 N2 C3 3_565 100.0(6)
N2 C2 N3 C8 . 0.1(6)
C1 C2 N3 C8 . 178.4(5)
C7 C8 N3 C2 . 180.0(6)
C3 C8 N3 C2 . -0.2(6)
N5 C10 N4 C11 . -1.4(6)
C9 C10 N4 C11 . 178.4(5)
N5 C10 N4 Cu1 . 179.0(4)
C9 C10 N4 Cu1 . -1.1(6)
C12 C11 N4 C10 . 178.5(6)
C16 C11 N4 C10 . 2.0(6)
C12 C11 N4 Cu1 . -2.2(10)
C16 C11 N4 Cu1 . -178.7(4)
N2 Cu1 N4 C10 . -11.6(9)
N6 Cu1 N4 C10 . 156.8(4)
N1 Cu1 N4 C10 . -12.3(4)
O4 Cu1 N4 C10 . -102.6(4)
N6 Cu1 N4 C10 3_565 69.8(4)
N2 Cu1 N4 C11 . 169.1(6)
N6 Cu1 N4 C11 . -22.5(6)
N1 Cu1 N4 C11 . 168.4(6)
O4 Cu1 N4 C11 . 78.1(6)
N6 Cu1 N4 C11 3_565 -109.5(6)
N4 C10 N5 C16 . 0.3(6)
C9 C10 N5 C16 . -179.6(5)
C11 C16 N5 C10 . 0.9(6)
C15 C16 N5 C10 . -177.4(6)
N2 Cu1 N6 N7 . -97.0(5)
N4 Cu1 N6 N7 . 86.2(5)
N1 Cu1 N6 N7 . -178.9(9)
O4 Cu1 N6 N7 . -5.5(5)
N6 Cu1 N6 N7 3_565 -180.0(6)
