#------------------------------------------------------------------------------
#$Date: 2023-09-04 17:13:28 +0300 (Mon, 04 Sep 2023) $
#$Revision: 285986 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/97/1569769.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_1569769
loop_
_publ_author_name
'Aliyeva, Vusala A.'
'Gurbanov, Atash V.'
'Mahmoud, Abdallah G.'
'Gomila, Rosa M.'
'Frontera, Antonio'
'Mahmudov, Kamran T.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Chalcogen bonding in copper(II)-mediated synthesis.
;
_journal_issue                   0
_journal_name_full               'Faraday discussions'
_journal_page_first              77
_journal_page_last               95
_journal_paper_doi               10.1039/d2fd00160h
_journal_volume                  244
_journal_year                    2023
_chemical_formula_moiety         'C18 H24 Cu N12, 2(C4 N3 O2 Se)'
_chemical_formula_sum            'C26 H24 Cu N18 O4 Se2'
_chemical_formula_weight         874.09
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2022-10-18 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.361(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2710(4)
_cell_length_b                   20.2764(11)
_cell_length_c                   10.1890(5)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.27
_cell_volume                     1675.28(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            37974
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_min         2.273
_exptl_absorpt_coefficient_mu    2.889
_exptl_absorpt_correction_T_max  0.671
_exptl_absorpt_correction_T_min  0.432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_description       plate
_exptl_crystal_F_000             870
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0200
_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)+(0.0240P)²+0.9575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0489
_refine_ls_wR_factor_ref         0.0513
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3064
_reflns_number_total             3425
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2fd00160h5.cif
_cod_data_source_block           m8_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1569769
_shelx_shelxl_version_number     2019/1
_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.
;
_shelx_estimated_absorpt_t_min   0.458
_shelx_estimated_absorpt_t_max   0.688
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
Cu1 Cu 0.000000 0.500000 0.500000 0.01625(7) Uani 1 2 d S . P . .
Se1 Se 0.76954(2) 0.21616(2) 0.29487(2) 0.02276(6) Uani 1 1 d . . . . .
O1 O 0.47281(16) 0.38803(7) 0.07253(13) 0.0280(3) Uani 1 1 d . . . . .
O2 O 0.59547(16) 0.35411(7) -0.09133(12) 0.0265(3) Uani 1 1 d . . . . .
N1 N 0.61403(19) 0.27320(7) 0.21172(15) 0.0216(3) Uani 1 1 d . . . . .
N2 N 0.91379(18) 0.23980(7) 0.19299(15) 0.0219(3) Uani 1 1 d . . . . .
N3 N 1.0115(2) 0.33422(10) -0.05255(18) 0.0350(4) Uani 1 1 d . . . . .
N4 N 0.19908(19) 0.41746(7) 0.44652(15) 0.0224(3) Uani 1 1 d . . . . .
N5 N 0.32461(19) 0.37777(8) 0.29084(15) 0.0250(3) Uani 1 1 d . . . . .
H5N H 0.382406 0.378029 0.223877 0.030 Uiso 1 1 d R U . . .
N6 N 0.14621(17) 0.57280(7) 0.44951(13) 0.0171(3) Uani 1 1 d . . . . .
N7 N 0.28328(19) 0.63354(8) 0.33004(15) 0.0240(3) Uani 1 1 d . . . . .
H7N H 0.318602 0.648108 0.254702 0.029 Uiso 1 1 d R U . . .
N8 N 0.12416(18) 0.50331(7) 0.69463(14) 0.0179(3) Uani 1 1 d . . . . .
N9 N 0.28339(19) 0.46881(7) 0.88083(14) 0.0232(3) Uani 1 1 d . . . . .
H9N H 0.358425 0.444409 0.937776 0.028 Uiso 1 1 d R U . . .
C1 C 0.6745(2) 0.30335(8) 0.11887(16) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.8395(2) 0.28470(8) 0.10906(17) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.5727(2) 0.35308(8) 0.02592(17) 0.0188(3) Uani 1 1 d . . . . .
C4 C 0.9324(2) 0.31301(9) 0.01643(18) 0.0233(4) Uani 1 1 d . . . . .
C5 C 0.3003(2) 0.43054(9) 0.36459(18) 0.0235(4) Uani 1 1 d . . . . .
H5A H 0.350198 0.472339 0.358461 0.028 Uiso 1 1 calc R U . . .
C6 C 0.2347(2) 0.32712(10) 0.32769(19) 0.0268(4) Uani 1 1 d . . . . .
H6A H 0.227186 0.283403 0.293511 0.032 Uiso 1 1 calc R U . . .
C7 C 0.1578(2) 0.35199(9) 0.42352(18) 0.0240(4) Uani 1 1 d . . . . .
H7A H 0.086287 0.327764 0.468003 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1581(2) 0.59147(9) 0.32758(18) 0.0232(4) Uani 1 1 d . . . . .
H8A H 0.086825 0.576870 0.248147 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3561(3) 0.64298(11) 0.4607(2) 0.0342(5) Uani 1 1 d . . . . .
H9A H 0.448187 0.670388 0.493935 0.041 Uiso 1 1 calc R U . . .
C10 C 0.2712(2) 0.60559(10) 0.53360(19) 0.0287(4) Uani 1 1 d . . . . .
H10A H 0.294182 0.602413 0.628480 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2450(2) 0.46269(8) 0.74672(17) 0.0207(3) Uani 1 1 d . . . . .
H11A H 0.297768 0.433142 0.696205 0.025 Uiso 1 1 calc R U . . .
C12 C 0.1823(2) 0.51576(9) 0.91668(18) 0.0241(4) Uani 1 1 d . . . . .
H12A H 0.180467 0.530474 1.004895 0.029 Uiso 1 1 calc R U . . .
C13 C 0.0848(2) 0.53736(9) 0.80176(17) 0.0212(4) Uani 1 1 d . . . . .
H13A H 0.002636 0.570558 0.795806 0.025 Uiso 1 1 calc R U . . .
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'
Se Se -0.0929 2.2259 '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
N6 Cu1 N6 180.00(5) 3_566 . ?
N6 Cu1 N8 89.34(5) 3_566 . ?
N6 Cu1 N8 90.66(5) . . ?
N6 Cu1 N8 90.66(5) 3_566 3_566 ?
N6 Cu1 N8 89.34(5) . 3_566 ?
N8 Cu1 N8 180.0 . 3_566 ?
N2 Se1 N1 92.91(7) . . ?
C1 N1 Se1 107.44(12) . . ?
C2 N2 Se1 106.40(12) . . ?
C5 N4 C7 104.62(15) . . ?
C5 N5 C6 107.20(16) . . ?
C5 N5 H5N 125.1 . . ?
C6 N5 H5N 127.5 . . ?
C8 N6 C10 105.12(15) . . ?
C8 N6 Cu1 127.09(12) . . ?
C10 N6 Cu1 127.08(11) . . ?
C8 N7 C9 107.42(15) . . ?
C8 N7 H7N 124.0 . . ?
C9 N7 H7N 128.1 . . ?
C11 N8 C13 105.71(14) . . ?
C11 N8 Cu1 124.30(12) . . ?
C13 N8 Cu1 129.02(12) . . ?
C11 N9 C12 107.58(15) . . ?
C11 N9 H9N 126.4 . . ?
C12 N9 H9N 126.0 . . ?
N1 C1 C2 115.55(15) . . ?
N1 C1 C3 121.19(15) . . ?
C2 C1 C3 123.23(15) . . ?
N2 C2 C1 117.69(16) . . ?
N2 C2 C4 117.27(15) . . ?
C1 C2 C4 125.01(15) . . ?
O2 C3 O1 126.19(16) . . ?
O2 C3 C1 116.04(15) . . ?
O1 C3 C1 117.76(15) . . ?
N3 C4 C2 176.9(2) . . ?
N4 C5 N5 112.12(17) . . ?
N4 C5 H5A 123.9 . . ?
N5 C5 H5A 123.9 . . ?
C7 C6 N5 105.99(16) . . ?
C7 C6 H6A 127.0 . . ?
N5 C6 H6A 127.0 . . ?
C6 C7 N4 110.07(17) . . ?
C6 C7 H7A 125.0 . . ?
N4 C7 H7A 125.0 . . ?
N6 C8 N7 111.47(16) . . ?
N6 C8 H8A 124.3 . . ?
N7 C8 H8A 124.3 . . ?
C10 C9 N7 106.32(17) . . ?
C10 C9 H9A 126.8 . . ?
N7 C9 H9A 126.8 . . ?
C9 C10 N6 109.67(16) . . ?
C9 C10 H10A 125.2 . . ?
N6 C10 H10A 125.2 . . ?
N8 C11 N9 110.98(16) . . ?
N8 C11 H11A 124.5 . . ?
N9 C11 H11A 124.5 . . ?
C13 C12 N9 106.60(16) . . ?
C13 C12 H12A 126.7 . . ?
N9 C12 H12A 126.7 . . ?
C12 C13 N8 109.12(16) . . ?
C12 C13 H13A 125.4 . . ?
N8 C13 H13A 125.4 . . ?
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
Cu1 N6 2.0375(14) 3_566 ?
Cu1 N6 2.0375(14) . ?
Cu1 N8 2.0468(14) . ?
Cu1 N8 2.0468(14) 3_566 ?
Se1 N2 1.7941(15) . ?
Se1 N1 1.8111(15) . ?
O1 C3 1.251(2) . ?
O2 C3 1.246(2) . ?
N1 C1 1.306(2) . ?
N2 C2 1.316(2) . ?
N3 C4 1.135(2) . ?
N4 C5 1.321(2) . ?
N4 C7 1.379(2) . ?
N5 C5 1.345(2) . ?
N5 C6 1.363(3) . ?
N5 H5N 0.9069 . ?
N6 C8 1.321(2) . ?
N6 C10 1.377(2) . ?
N7 C8 1.338(2) . ?
N7 C9 1.362(3) . ?
N7 H7N 0.9221 . ?
N8 C11 1.323(2) . ?
N8 C13 1.383(2) . ?
N9 C11 1.346(2) . ?
N9 C12 1.364(2) . ?
N9 H9N 0.9082 . ?
C1 C2 1.439(2) . ?
C1 C3 1.519(2) . ?
C2 C4 1.448(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.363(3) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 C10 1.351(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C13 1.357(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
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
N5 H5N O1 0.91 1.85 2.751(2) 170.3 . yes
N7 H7N O2 0.92 1.93 2.8187(19) 159.9 3_665 yes
N9 H9N O1 0.91 1.89 2.7833(19) 167.0 1_556 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Se1 N1 C1 0.78(12) . . . . ?
N1 Se1 N2 C2 -0.81(12) . . . . ?
Se1 N1 C1 C2 -0.55(18) . . . . ?
Se1 N1 C1 C3 177.63(12) . . . . ?
Se1 N2 C2 C1 0.67(18) . . . . ?
Se1 N2 C2 C4 178.85(13) . . . . ?
N1 C1 C2 N2 -0.1(2) . . . . ?
C3 C1 C2 N2 -178.23(15) . . . . ?
N1 C1 C2 C4 -178.10(16) . . . . ?
C3 C1 C2 C4 3.7(3) . . . . ?
N1 C1 C3 O2 -144.66(17) . . . . ?
C2 C1 C3 O2 33.4(2) . . . . ?
N1 C1 C3 O1 34.1(2) . . . . ?
C2 C1 C3 O1 -147.85(17) . . . . ?
C7 N4 C5 N5 0.5(2) . . . . ?
C6 N5 C5 N4 -0.5(2) . . . . ?
C5 N5 C6 C7 0.3(2) . . . . ?
N5 C6 C7 N4 0.0(2) . . . . ?
C5 N4 C7 C6 -0.3(2) . . . . ?
C10 N6 C8 N7 0.4(2) . . . . ?
Cu1 N6 C8 N7 -170.48(12) . . . . ?
C9 N7 C8 N6 -0.3(2) . . . . ?
C8 N7 C9 C10 0.1(2) . . . . ?
N7 C9 C10 N6 0.1(3) . . . . ?
C8 N6 C10 C9 -0.3(2) . . . . ?
Cu1 N6 C10 C9 170.57(15) . . . . ?
C13 N8 C11 N9 0.5(2) . . . . ?
Cu1 N8 C11 N9 -169.16(11) . . . . ?
C12 N9 C11 N8 -0.1(2) . . . . ?
C11 N9 C12 C13 -0.3(2) . . . . ?
N9 C12 C13 N8 0.6(2) . . . . ?
C11 N8 C13 C12 -0.7(2) . . . . ?
Cu1 N8 C13 C12 168.28(12) . . . . ?
