#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/16/2231658.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_2231658
loop_
_publ_author_name
'Yu, Rui-Jin'
'Deng, Bin'
_publ_section_title
;
 Bis(cyanamide-κN)[4-(1H-imidazol-1-yl)phenol-κN³]bis(nitrato-κO)copper(II)
;
_journal_coeditor_code           PK2338
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1253
_journal_paper_doi               10.1107/S1600536811032399
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu (N O3)2 (C9 H8 N2 O)2 (C H2 N2)2]'
_chemical_formula_moiety         'C20 H20 Cu N10 O8'
_chemical_formula_sum            'C20 H20 Cu N10 O8'
_chemical_formula_weight         592.00
_chemical_name_systematic
;
Bis(cyanamide-κN)[4-(1H-imidazol-1-yl)phenol-
κN³]bis(nitrato-κO)copper(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.8080(10)
_cell_angle_beta                 96.696(2)
_cell_angle_gamma                98.883(2)
_cell_formula_units_Z            1
_cell_length_a                   8.2235(7)
_cell_length_b                   8.7144(8)
_cell_length_c                   9.4553(9)
_cell_measurement_reflns_used    2396
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.35
_cell_volume                     614.92(10)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4951
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_T_max  0.847
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             303
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.2239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                2229
_reflns_number_total             2396
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2338.cif
_cod_data_source_block           I
_cod_database_code               2231658
_cod_database_fobs_code          2231658
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cu Cu1 0.0000 0.5000 0.0000 0.03730(17) Uani d S 1 2
O O1 1.0200(2) 1.3124(2) 0.3638(2) 0.0522(5) Uani d . 1 1
H HO1 1.0559 1.3039 0.2822 0.078 Uiso d R 1 1
O O3 0.1612(2) 0.3321(3) 0.1247(2) 0.0588(5) Uani d . 1 1
O O4 0.3655(3) 0.4115(4) 0.3168(3) 0.0738(7) Uani d . 1 1
O O2 0.4149(3) 0.4075(3) 0.0983(2) 0.0598(5) Uani d . 1 1
N N1 -0.1364(3) 0.5376(3) 0.1629(3) 0.0465(5) Uani d . 1 1
N N2 -0.2913(3) 0.5888(3) 0.3748(3) 0.0516(6) Uani d . 1 1
H HN2B -0.3876 0.5230 0.3578 0.062 Uiso d R 1 1
H HN2A -0.2331 0.6083 0.4636 0.062 Uiso d R 1 1
N N3 0.1547(3) 0.7184(2) 0.1239(2) 0.0390(5) Uani d . 1 1
N N4 0.3757(2) 0.9254(2) 0.2240(2) 0.0389(5) Uani d . 1 1
N N5 0.3155(3) 0.3834(3) 0.1788(3) 0.0433(5) Uani d . 1 1
C C1 0.1064(3) 0.8598(3) 0.2122(3) 0.0473(6) Uani d . 1 1
H H1 -0.0025 0.8663 0.2274 0.057 Uiso calc R 1 1
C C2 0.2407(3) 0.9884(3) 0.2740(3) 0.0484(7) Uani d . 1 1
H H2 0.2417 1.0981 0.3378 0.058 Uiso calc R 1 1
C C3 0.3189(3) 0.7628(3) 0.1334(3) 0.0392(6) Uani d . 1 1
H H3 0.3853 0.6910 0.0841 0.047 Uiso calc R 1 1
C C4 0.5449(3) 1.0196(3) 0.2591(3) 0.0372(5) Uani d . 1 1
C C5 0.6081(3) 1.1383(3) 0.4066(3) 0.0459(6) Uani d . 1 1
H H5 0.5432 1.1533 0.4828 0.055 Uiso calc R 1 1
C C6 0.7685(3) 1.2339(3) 0.4393(3) 0.0460(6) Uani d . 1 1
H H6 0.8122 1.3130 0.5381 0.055 Uiso calc R 1 1
C C7 0.8639(3) 1.2124(3) 0.3258(3) 0.0393(6) Uani d . 1 1
C C8 0.8007(3) 1.0926(3) 0.1790(3) 0.0427(6) Uani d . 1 1
H H8 0.8656 1.0774 0.1028 0.051 Uiso calc R 1 1
C C9 0.6406(3) 0.9957(3) 0.1462(3) 0.0415(6) Uani d . 1 1
H H9 0.5980 0.9146 0.0481 0.050 Uiso calc R 1 1
C C10 -0.2100(3) 0.5568(3) 0.2602(3) 0.0387(6) Uani 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'
Cu Cu 0.3201 1.2651 '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'
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
N1 Cu1 N1 . 2_565 180.00(14)
N1 Cu1 N3 . . 89.82(9)
N1 Cu1 N3 2_565 . 90.18(8)
N1 Cu1 N3 . 2_565 90.18(9)
N1 Cu1 N3 2_565 2_565 89.82(8)
N3 Cu1 N3 . 2_565 180.0
C7 O1 HO1 . . 108.5
C10 N1 Cu1 . . 177.0(2)
C10 N2 HN2B . . 116.0
C10 N2 HN2A . . 115.8
HN2B N2 HN2A . . 112.2
C3 N3 C1 . . 106.0(2)
C3 N3 Cu1 . . 129.22(18)
C1 N3 Cu1 . . 124.71(17)
C3 N4 C2 . . 107.3(2)
C3 N4 C4 . . 127.0(2)
C2 N4 C4 . . 125.7(2)
O2 N5 O4 . . 120.4(2)
O2 N5 O3 . . 120.9(2)
O4 N5 O3 . . 118.8(2)
C2 C1 N3 . . 109.6(2)
C2 C1 H1 . . 125.2
N3 C1 H1 . . 125.2
C1 C2 N4 . . 106.5(2)
C1 C2 H2 . . 126.8
N4 C2 H2 . . 126.8
N3 C3 N4 . . 110.7(2)
N3 C3 H3 . . 124.7
N4 C3 H3 . . 124.7
C9 C4 C5 . . 120.6(2)
C9 C4 N4 . . 120.2(2)
C5 C4 N4 . . 119.1(2)
C6 C5 C4 . . 119.4(3)
C6 C5 H5 . . 120.3
C4 C5 H5 . . 120.3
C7 C6 C5 . . 120.2(2)
C7 C6 H6 . . 119.9
C5 C6 H6 . . 119.9
O1 C7 C6 . . 117.7(2)
O1 C7 C8 . . 122.1(2)
C6 C7 C8 . . 120.2(2)
C9 C8 C7 . . 119.7(2)
C9 C8 H8 . . 120.1
C7 C8 H8 . . 120.1
C4 C9 C8 . . 119.8(2)
C4 C9 H9 . . 120.1
C8 C9 H9 . . 120.1
N1 C10 N2 . . 176.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 N1 . 1.974(2)
Cu1 N1 2_565 1.974(2)
Cu1 N3 . 1.9837(19)
Cu1 N3 2_565 1.9837(19)
O1 C7 . 1.365(3)
O1 HO1 . 0.8409
O3 N5 . 1.259(3)
O4 N5 . 1.244(3)
O2 N5 . 1.224(3)
N1 C10 . 1.136(3)
N2 C10 . 1.308(3)
N2 HN2B . 0.8638
N2 HN2A . 0.8613
N3 C3 . 1.329(3)
N3 C1 . 1.368(3)
N4 C3 . 1.342(3)
N4 C2 . 1.372(3)
N4 C4 . 1.438(3)
C1 C2 . 1.349(4)
C1 H1 . 0.9300
C2 H2 . 0.9300
C3 H3 . 0.9300
C4 C9 . 1.375(4)
C4 C5 . 1.388(4)
C5 C6 . 1.383(4)
C5 H5 . 0.9300
C6 C7 . 1.378(4)
C6 H6 . 0.9300
C7 C8 . 1.386(4)
C8 C9 . 1.385(3)
C8 H8 . 0.9300
C9 H9 . 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
O1 HO1 O3 1_665 0.84 1.88 2.704(3) 167.8
O1 HO1 O4 1_665 0.84 2.51 2.970(3) 115.2
O1 HO1 N5 1_665 0.84 2.55 3.262(3) 143.1
N2 HN2B O4 1_455 0.86 2.04 2.888(3) 167.7
N2 HN2B O2 1_455 0.86 2.55 3.096(3) 122.3
N2 HN2B N5 1_455 0.86 2.64 3.399(3) 147.5
N2 HN2A O1 2_676 0.86 2.09 2.904(3) 157.3
N2 HN2A O4 2_566 0.86 2.50 3.049(3) 122.3
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139081932
