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#$Date: 2025-10-30 01:45:39 +0200 (Thu, 30 Oct 2025) $
#$Revision: 303097 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/11/7251157.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7251157
loop_
_publ_author_name
'Fokin, Sergey V.'
'Tolstikov, Svyatoslav E.'
'Morozov, Vitaliy A.'
'Samsonenko, Arkady A.'
'Romanenko, Galina'
'Bogomyakov, Artem'
_publ_section_title
;
 Aqua and ammine 3d metal complexes with anion-radical of
 difurazanopyrazine
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00836K
_journal_year                    2025
_chemical_formula_sum            'C8 H12 Cu N16 O4'
_chemical_formula_weight         459.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-12-05 deposited with the CCDC.	2025-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.1066(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3743(3)
_cell_length_b                   10.4991(4)
_cell_length_c                   9.5646(4)
_cell_measurement_reflns_used    5083
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.53
_cell_measurement_theta_min      6.15
_cell_volume                     799.30(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7965
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.556
_diffrn_reflns_theta_max         67.556
_diffrn_reflns_theta_min         6.147
_exptl_absorpt_coefficient_mu    2.547
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_description       prism
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1439
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0605P)²+0.1707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0866
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1362
_reflns_number_total             1439
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00836k2.cif
_cod_data_source_block           515
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7251157
_shelx_shelxl_version_number     2018/3
_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. 
;
loop_
_space_group_symop_operation_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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.500000 -0.500000 0.500000 0.03432(17) Uani 1 2 d S . P . .
O1 O 0.1835(2) -0.57935(16) 0.87305(16) 0.0570(4) Uani 1 1 d . . . . .
N2 N 0.2662(2) -0.57337(16) 0.76721(18) 0.0449(4) Uani 1 1 d . . . . .
C3 C 0.1915(2) -0.47907(16) 0.68103(19) 0.0304(4) Uani 1 1 d . . . . .
N4 N 0.22952(16) -0.43832(13) 0.56115(15) 0.0303(3) Uani 1 1 d . . . . .
C5 C 0.12641(19) -0.34203(15) 0.49892(17) 0.0287(3) Uani 1 1 d . . . . .
N6 N 0.12699(19) -0.27979(15) 0.37889(17) 0.0402(4) Uani 1 1 d . . . . .
O7 O -0.00184(18) -0.19093(14) 0.35747(16) 0.0500(4) Uani 1 1 d . . . . .
N8 N -0.0831(2) -0.19803(16) 0.4626(2) 0.0465(4) Uani 1 1 d . . . . .
C9 C -0.00546(19) -0.29016(16) 0.55114(19) 0.0322(3) Uani 1 1 d . . . . .
N10 N -0.04372(18) -0.33107(15) 0.67045(17) 0.0382(3) Uani 1 1 d . . . . .
C11 C 0.0596(2) -0.42705(17) 0.73257(18) 0.0339(4) Uani 1 1 d . . . . .
N12 N 0.0561(3) -0.49052(18) 0.8509(2) 0.0523(5) Uani 1 1 d . . . . .
N1H N 0.4399(2) -0.68836(15) 0.4791(2) 0.0412(4) Uani 1 1 d D . . . .
H11 H 0.537(4) -0.739(4) 0.483(5) 0.138(18) Uiso 1 1 d D . . . .
H12 H 0.326(3) -0.698(4) 0.413(3) 0.099(11) Uiso 1 1 d D . . . .
H13 H 0.430(6) -0.730(4) 0.560(3) 0.121(14) Uiso 1 1 d D . . . .
N2H N 0.6279(2) -0.5301(2) 0.71663(19) 0.0396(4) Uani 1 1 d . . . . .
H21 H 0.575(6) -0.527(4) 0.770(5) 0.096(13) Uiso 1 1 d . . . . .
H22 H 0.689(5) -0.476(4) 0.755(5) 0.089(13) Uiso 1 1 d . . . . .
H23 H 0.684(5) -0.586(4) 0.724(4) 0.096(13) Uiso 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1H Cu N1H 180.0 . 3_646 ?
N1H Cu N2H 89.13(8) . . ?
N1H Cu N2H 90.87(8) 3_646 . ?
N1H Cu N2H 90.87(8) . 3_646 ?
N1H Cu N2H 89.12(8) 3_646 3_646 ?
N2H Cu N2H 180.0 . 3_646 ?
N1H Cu N4 93.33(5) . . ?
N1H Cu N4 86.67(5) 3_646 . ?
N2H Cu N4 91.67(6) . . ?
N2H Cu N4 88.32(6) 3_646 . ?
N1H Cu N4 86.67(5) . 3_646 ?
N1H Cu N4 93.33(5) 3_646 3_646 ?
N2H Cu N4 88.32(6) . 3_646 ?
N2H Cu N4 91.68(6) 3_646 3_646 ?
N4 Cu N4 180.0 . 3_646 ?
N12 O1 N2 113.06(14) . . ?
C3 N2 O1 104.02(15) . . ?
N2 C3 N4 125.34(16) . . ?
N2 C3 C11 109.56(16) . . ?
N4 C3 C11 125.09(16) . . ?
C5 N4 C3 109.02(13) . . ?
C5 N4 Cu 125.10(10) . . ?
C3 N4 Cu 124.43(11) . . ?
N6 C5 N4 125.57(14) . . ?
N6 C5 C9 108.76(15) . . ?
N4 C5 C9 125.67(14) . . ?
C5 N6 O7 104.31(13) . . ?
N8 O7 N6 113.04(13) . . ?
C9 N8 O7 104.57(14) . . ?
N8 C9 N10 125.37(16) . . ?
N8 C9 C5 109.32(16) . . ?
N10 C9 C5 125.31(15) . . ?
C11 N10 C9 108.92(13) . . ?
N12 C11 N10 125.13(16) . . ?
N12 C11 C3 108.87(17) . . ?
N10 C11 C3 126.00(15) . . ?
C11 N12 O1 104.49(16) . . ?
Cu N1H H11 110(3) . . ?
Cu N1H H12 109(2) . . ?
H11 N1H H12 128(3) . . ?
Cu N1H H13 118(3) . . ?
H11 N1H H13 90(4) . . ?
H12 N1H H13 100(4) . . ?
Cu N2H H21 116(3) . . ?
Cu N2H H22 115(3) . . ?
H21 N2H H22 95(4) . . ?
Cu N2H H23 109(3) . . ?
H21 N2H H23 117(4) . . ?
H22 N2H H23 103(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu N1H 2.0351(16) . ?
Cu N1H 2.0351(16) 3_646 ?
Cu N2H 2.0398(17) . ?
Cu N2H 2.0398(17) 3_646 ?
Cu N4 2.5914(13) . ?
Cu N4 2.5915(13) 3_646 ?
O1 N12 1.383(3) . ?
O1 N2 1.394(2) . ?
N2 C3 1.315(2) . ?
C3 N4 1.351(2) . ?
C3 C11 1.449(2) . ?
N4 C5 1.343(2) . ?
C5 N6 1.322(2) . ?
C5 C9 1.452(2) . ?
N6 O7 1.392(2) . ?
O7 N8 1.381(2) . ?
N8 C9 1.316(2) . ?
C9 N10 1.348(2) . ?
N10 C11 1.341(2) . ?
C11 N12 1.321(2) . ?
N1H H11 0.962(19) . ?
N1H H12 0.973(19) . ?
N1H H13 0.916(19) . ?
N2H H21 0.77(5) . ?
N2H H22 0.78(4) . ?
N2H H23 0.74(5) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1H H12 N10 0.973(19) 2.27(2) 3.185(2) 157(3) 3_546 yes
N2H H21 N2 0.77(5) 2.62(5) 3.244(3) 139(4) . yes
N2H H21 O7 0.77(5) 2.59(4) 3.048(2) 120(3) 4_656 yes
N2H H23 N6 0.74(5) 2.53(4) 3.193(2) 149(4) 3_646 yes
