#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/12/2241259.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_2241259
loop_
_publ_author_name
'Liu, Chen'
'Abboud, Khalil A.'
_publ_section_title
;
 Crystal structures of μ-oxalato-bis[azido(histamine)copper(II)] and
 μ-oxalato-bis[(dicyanamido)(histamine)copper(II)]
;
_journal_coeditor_code           ZL2645
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1379
_journal_page_last               1383
_journal_paper_doi               10.1107/S2056989015019908
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '[Cu2 (C2 O4) (N3)2 (C5 H9 N3)2]'
_chemical_formula_sum            'C12 H18 Cu2 N12 O4'
_chemical_formula_weight         521.46
_chemical_name_systematic
μ-Oxalato-κ⁴O¹,O²:O^1'^,O^2'^-bis[[4-(2-aminoethyl)-1H-imidazole-κ²N³,N⁴](azido-κN¹)copper(II)]
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4419(7)
_cell_length_b                   7.4576(4)
_cell_length_c                   17.7662(9)
_cell_measurement_reflns_used    88
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     1780.96(16)
_computing_cell_refinement
;
SMART and SAINT (Bruker, 1998)
;
_computing_data_collection
;
SMART (Bruker, 1998)
;
_computing_data_reduction
;
SAINT (Bruker, 1998)
;
_computing_molecular_graphics
;
SHELXTL-Plus (Sheldrick, 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10138
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.293
_exptl_absorpt_coefficient_mu    2.442
_exptl_absorpt_correction_T_max  0.8353
_exptl_absorpt_correction_T_min  0.6818
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(SADABS; Bruker, 1998)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.945
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.255
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0279P)²+1.2918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                1768
_reflns_number_total             2027
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zl2645sup1.cif
_cod_data_source_block           I
_cod_database_code               2241259
_cod_database_fobs_code          2241259
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_occupancy
Cu Cu1 0.44296(2) 0.24198(3) 0.59064(2) 0.01472(11) Uani d 1
O O1 0.47496(11) 0.27517(17) 0.48108(7) 0.0173(3) Uani d 1
O O2 0.46843(11) 0.50801(17) 0.59516(7) 0.0181(3) Uani d 1
N N1 0.60261(13) 0.1548(2) 0.60977(10) 0.0221(4) Uani d 1
N N2 0.65931(13) 0.2515(2) 0.57879(9) 0.0182(3) Uani d 1
N N3 0.71372(14) 0.3492(3) 0.54767(10) 0.0301(4) Uani d 1
N N4 0.39863(12) 0.23846(19) 0.69487(9) 0.0159(3) Uani d 1
N N5 0.36694(12) 0.3189(2) 0.81078(9) 0.0199(3) Uani d 1
H H5 0.3614 0.3858 0.8514 0.024 Uiso calc 1
N N6 0.37467(14) 0.0143(2) 0.56327(9) 0.0182(3) Uani d 1
H H6A 0.3427(19) 0.035(3) 0.5215(14) 0.025(6) Uiso d 1
H H6B 0.420(2) -0.065(4) 0.5489(14) 0.027(6) Uiso d 1
C C1 0.49805(13) 0.5671(2) 0.53301(10) 0.0156(4) Uani d 1
C C2 0.39970(14) 0.3740(3) 0.74353(10) 0.0187(4) Uani d 1
H H2A 0.4207 0.4926 0.7322 0.022 Uiso calc 1
C C3 0.34345(15) 0.1401(3) 0.80562(11) 0.0203(4) Uani d 1
H H3A 0.3182 0.0661 0.8447 0.024 Uiso calc 1
C C4 0.36342(14) 0.0895(2) 0.73347(10) 0.0164(4) Uani d 1
C C5 0.35239(15) -0.0881(2) 0.69514(11) 0.0187(4) Uani d 1
H H5A 0.3107 -0.1673 0.7268 0.022 Uiso calc 1
H H5B 0.4188 -0.1445 0.6903 0.022 Uiso calc 1
C C6 0.30567(14) -0.0729(3) 0.61751(11) 0.0188(4) Uani d 1
H H6C 0.2882 -0.1941 0.5990 0.023 Uiso calc 1
H H6D 0.2436 -0.0019 0.6210 0.023 Uiso calc 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_1
_geom_angle_site_symmetry_3
_geom_angle
N4 Cu1 N6 . . 94.58(7)
N4 Cu1 O1 . . 171.72(6)
N6 Cu1 O1 . . 88.11(6)
N4 Cu1 O2 . . 91.58(6)
N6 Cu1 O2 . . 158.12(7)
O1 Cu1 O2 . . 83.16(5)
N4 Cu1 N1 . . 98.24(6)
N6 Cu1 N1 . . 103.21(7)
O1 Cu1 N1 . . 88.73(6)
O2 Cu1 N1 . . 96.63(6)
C1 O1 Cu1 5_666 . 111.73(11)
C1 O2 Cu1 . . 111.40(11)
N2 N1 Cu1 . . 111.39(13)
N3 N2 N1 . . 178.6(2)
C2 N4 C4 . . 106.89(16)
C2 N4 Cu1 . . 127.24(13)
C4 N4 Cu1 . . 125.82(12)
C2 N5 C3 . . 108.30(16)
C2 N5 H5 . . 125.8
C3 N5 H5 . . 125.8
C6 N6 Cu1 . . 120.15(12)
C6 N6 H6A . . 108.7(16)
Cu1 N6 H6A . . 106.6(16)
C6 N6 H6B . . 108.9(16)
Cu1 N6 H6B . . 108.7(17)
H6A N6 H6B . . 102(2)
O2 C1 O1 . 5_666 126.59(17)
O2 C1 C1 . 5_666 116.9(2)
O1 C1 C1 5_666 5_666 116.48(19)
N4 C2 N5 . . 110.11(17)
N4 C2 H2A . . 124.9
N5 C2 H2A . . 124.9
C4 C3 N5 . . 106.62(16)
C4 C3 H3A . . 126.7
N5 C3 H3A . . 126.7
C3 C4 N4 . . 108.08(16)
C3 C4 C5 . . 130.79(17)
N4 C4 C5 . . 121.13(16)
C4 C5 C6 . . 112.82(16)
C4 C5 H5A . . 109.0
C6 C5 H5A . . 109.0
C4 C5 H5B . . 109.0
C6 C5 H5B . . 109.0
H5A C5 H5B . . 107.8
N6 C6 C5 . . 111.28(16)
N6 C6 H6C . . 109.4
C5 C6 H6C . . 109.4
N6 C6 H6D . . 109.4
C5 C6 H6D . . 109.4
H6C C6 H6D . . 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 N4 . 1.9454(16)
Cu1 N6 . 1.9904(17)
Cu1 O1 . 2.0088(13)
Cu1 O2 . 2.0148(13)
Cu1 N1 . 2.2679(17)
O1 C1 5_666 1.257(2)
O2 C1 . 1.254(2)
N1 N2 . 1.185(2)
N2 N3 . 1.171(2)
N4 C2 . 1.330(2)
N4 C4 . 1.388(2)
N5 C2 . 1.338(2)
N5 C3 . 1.374(3)
N5 H5 . 0.8800
N6 C6 . 1.487(2)
N6 H6A . 0.87(3)
N6 H6B . 0.89(3)
C1 O1 5_666 1.257(2)
C1 C1 5_666 1.542(4)
C2 H2A . 0.9500
C3 C4 . 1.363(3)
C3 H3 . 0.9500
C4 C5 . 1.497(3)
C5 C6 . 1.520(3)
C5 H5A . 0.9900
C5 H5B . 0.9900
C6 H6C . 0.9900
C6 H6D . 0.9900
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
N5 H5 N1 3_656 0.88 2.18 2.904(2) 139.8
N5 H5 N3 6_557 0.88 2.69 3.258(2) 123.5
N6 H6A N3 4_456 0.87(3) 2.29(3) 3.099(3) 154(2)
N6 H6B O1 5_656 0.89(3) 2.17(3) 3.061(2) 175(2)
C3 H3 N3 3_646 0.95 2.54 3.476(8) 168.6
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168326400
