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#$Date: 2022-03-03 04:15:33 +0200 (Thu, 03 Mar 2022) $
#$Revision: 273216 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/45/7244558.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_7244558
loop_
_publ_author_name
'Finko, Alexander V.'
'Sokolov, Anatolii I.'
'Guk, Dmitry A.'
'Tafeenko, Victor A.'
'Moiseeva, Anna A.'
'Skvortsov, Dmitry A.'
'Stomakhin, Andrei A.'
'Beloglazkin, Andrei A.'
'Borisov, Roman S.'
'Pergushov, Vladimir I.'
'Melnikov, Mikhail Ya.'
'Zyk, Nikolay V.'
'Majouga, Alexander G.'
'Beloglazkina, Elena K.'
_publ_section_title
;
 Copper coordination compounds with
 (5Z,5Z′)-2,2′-(alkane-α,ω-diyldiselenyl)-bis-5-(2-pyridylmethylene)-3,5-dihydro-4H-imidazol-4-ones.
 Comparison with sulfur analogue
;
_journal_issue                   12
_journal_name_full               'RSC Advances'
_journal_page_first              7133
_journal_page_last               7148
_journal_paper_doi               10.1039/D1RA08995A
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C15 H16 Cl2 Cu N3 O Se'
_chemical_formula_sum            'C15 H16 Cl2 Cu N3 O Se'
_chemical_formula_weight         467.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-11-30 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.406(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.8120(10)
_cell_length_b                   10.3367(4)
_cell_length_c                   13.4574(6)
_cell_measurement_reflns_used    6254
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      64.4
_cell_measurement_theta_min      4.60
_cell_volume                     3403.0(3)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      295
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  STOE
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_av_unetI/netI     0.0980
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16893
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.990
_diffrn_reflns_theta_max         66.990
_diffrn_reflns_theta_min         3.614
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    7.201
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_refine_diff_density_max         1.057
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2989
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.1388
_refine_ls_R_factor_gt           0.0711
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1292P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1859
_refine_ls_wR_factor_ref         0.2199
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1357
_reflns_number_total             2989
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra08995a2.cif
_cod_data_source_block           dgcpc6_k
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7244558
_shelx_shelxl_version_number     2016/6
_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.60753(6) 0.31797(11) 0.61964(12) 0.0722(5) Uani 1 1 d . . . . .
Cl1 Cl 0.64706(11) 0.1263(2) 0.6327(3) 0.0867(8) Uani 1 1 d . . . . .
Cl2 Cl 0.63343(12) 0.4102(2) 0.5012(2) 0.0875(8) Uani 1 1 d . . . . .
O1 O 0.5264(3) 0.7601(6) 0.6602(6) 0.088(2) Uani 1 1 d . . . . .
N1 N 0.5381(3) 0.2534(7) 0.6229(7) 0.070(2) Uani 1 1 d . . . . .
N2 N 0.6064(3) 0.4811(6) 0.6951(6) 0.0632(19) Uani 1 1 d . . . . .
N3 N 0.6168(3) 0.6977(6) 0.7300(6) 0.066(2) Uani 1 1 d . . . . .
C2 C 0.5278(5) 0.1259(9) 0.6183(9) 0.076(3) Uani 1 1 d . . . . .
H2 H 0.555852 0.069075 0.629300 0.091 Uiso 1 1 calc R U . . .
C3 C 0.4783(5) 0.0741(9) 0.5984(9) 0.081(3) Uani 1 1 d . . . . .
H3 H 0.473735 -0.015041 0.598205 0.097 Uiso 1 1 calc R U . . .
C4 C 0.4360(5) 0.1563(10) 0.5788(9) 0.081(3) Uani 1 1 d . . . . .
H4 H 0.401189 0.124889 0.558825 0.098 Uiso 1 1 calc R U . . .
C5 C 0.4470(5) 0.2885(9) 0.5901(9) 0.079(3) Uani 1 1 d . . . . .
H5 H 0.419873 0.346618 0.582062 0.095 Uiso 1 1 calc R U . . .
C6 C 0.4980(4) 0.3338(8) 0.6131(8) 0.065(2) Uani 1 1 d . . . . .
C7 C 0.5081(4) 0.4724(8) 0.6288(8) 0.065(2) Uani 1 1 d . . . . .
H7 H 0.477560 0.523869 0.610150 0.078 Uiso 1 1 calc R U . . .
C8 C 0.5551(4) 0.5350(8) 0.6660(8) 0.064(2) Uani 1 1 d . . . . .
C9 C 0.5611(5) 0.6789(9) 0.6827(8) 0.068(3) Uani 1 1 d . . . . .
C10 C 0.6427(4) 0.5794(8) 0.7354(8) 0.065(2) Uani 1 1 d . . . . .
C11 C 0.6428(5) 0.8205(8) 0.7619(9) 0.078(3) Uani 1 1 d . . . . .
H11 H 0.6466(7) 0.856(5) 0.715(7) 0.094 Uiso 1 1 calc R U . . .
C12 C 0.6314(6) 0.9062(9) 0.8364(9) 0.091(4) Uani 1 1 d . . . . .
H12A H 0.628217 0.998263 0.820590 0.109 Uiso 1 1 calc R U . . .
H12B H 0.607754 0.873437 0.865158 0.109 Uiso 1 1 calc R U . . .
C13 C 0.6860(5) 0.8465(10) 0.8792(10) 0.088(3) Uani 1 1 d . . . . .
H13A H 0.695679 0.777233 0.934010 0.106 Uiso 1 1 calc R U . . .
H13B H 0.716146 0.902085 0.889432 0.106 Uiso 1 1 calc R U . . .
Se1 Se 0.71690(5) 0.58347(9) 0.78959(11) 0.0860(5) Uani 1 1 d . . . . .
C14 C 0.7361(5) 0.4009(10) 0.8012(11) 0.111(4) Uani 1 1 d D . . . .
H14A H 0.703659 0.347803 0.775831 0.133 Uiso 1 1 calc R U . . .
H14B H 0.753255 0.381795 0.754724 0.133 Uiso 1 1 calc R U . . .
C15 C 0.7753(8) 0.3736(16) 0.9238(13) 0.59(6) Uani 1 1 d D . . . .
H15A H 0.811990 0.376311 0.932490 0.710 Uiso 1 1 calc R U . . .
H15B H 0.772472 0.444794 0.967665 0.710 Uiso 1 1 calc R U . . .
C16 C 0.7705(7) 0.2510(16) 0.9776(19) 0.56(6) Uani 1 1 d D . . . .
H16A H 0.806281 0.230795 1.039806 0.673 Uiso 1 1 calc R U . . .
H16B H 0.761018 0.181924 0.922567 0.673 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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'
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'
Se Se -0.7943 1.1372 '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
N2 Cu1 N1 91.2(3) . . ?
N2 Cu1 Cl1 147.6(2) . . ?
N1 Cu1 Cl1 98.2(2) . . ?
N2 Cu1 Cl2 95.2(2) . . ?
N1 Cu1 Cl2 140.4(2) . . ?
Cl1 Cu1 Cl2 96.90(11) . . ?
C2 N1 C6 117.0(9) . . ?
C2 N1 Cu1 119.7(7) . . ?
C6 N1 Cu1 122.6(6) . . ?
C10 N2 C8 106.3(7) . . ?
C10 N2 Cu1 131.0(6) . . ?
C8 N2 Cu1 117.2(6) . . ?
C9 N3 C10 109.7(7) . . ?
C9 N3 C11 124.2(8) . . ?
C10 N3 C11 126.0(9) . . ?
N1 C2 C3 124.0(10) . . ?
N1 C2 H2 118.0 . . ?
C3 C2 H2 118.0 . . ?
C4 C3 C2 118.9(9) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 117.5(10) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
C6 C5 C4 120.5(10) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 C5 121.8(8) . . ?
N1 C6 C7 119.9(9) . . ?
C5 C6 C7 118.3(9) . . ?
C8 C7 C6 128.6(9) . . ?
C8 C7 H7 115.7 . . ?
C6 C7 H7 115.7 . . ?
C7 C8 N2 127.0(8) . . ?
C7 C8 C9 123.9(9) . . ?
N2 C8 C9 109.0(8) . . ?
O1 C9 N3 127.3(9) . . ?
O1 C9 C8 129.5(10) . . ?
N3 C9 C8 103.2(8) . . ?
N2 C10 N3 111.5(9) . . ?
N2 C10 Se1 131.5(6) . . ?
N3 C10 Se1 117.0(7) . . ?
N3 C11 C12 119.8(9) . . ?
N3 C11 C13 121.4(8) . . ?
C12 C11 C13 59.8(7) . . ?
N3 C11 H11 114.9 . . ?
C12 C11 H11 114.9 . . ?
C13 C11 H11 114.9 . . ?
C13 C12 C11 60.3(8) . . ?
C13 C12 H12A 117.7 . . ?
C11 C12 H12A 117.7 . . ?
C13 C12 H12B 117.7 . . ?
C11 C12 H12B 117.7 . . ?
H12A C12 H12B 114.9 . . ?
C12 C13 C11 59.9(7) . . ?
C12 C13 H13A 117.8 . . ?
C11 C13 H13A 117.8 . . ?
C12 C13 H13B 117.8 . . ?
C11 C13 H13B 117.8 . . ?
H13A C13 H13B 114.9 . . ?
C10 Se1 C14 102.9(5) . . ?
C15 C14 Se1 107.3(10) . . ?
C15 C14 H14A 110.3 . . ?
Se1 C14 H14A 110.3 . . ?
C15 C14 H14B 110.3 . . ?
Se1 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
C16 C15 C14 120.2(11) . . ?
C16 C15 H15A 107.3 . . ?
C14 C15 H15A 107.3 . . ?
C16 C15 H15B 107.3 . . ?
C14 C15 H15B 107.3 . . ?
H15A C15 H15B 106.9 . . ?
C15 C16 C16 117.3(11) . 7_657 ?
C15 C16 H16A 108.0 . . ?
C16 C16 H16A 108.0 7_657 . ?
C15 C16 H16B 108.0 . . ?
C16 C16 H16B 108.0 7_657 . ?
H16A C16 H16B 107.2 . . ?
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 N2 1.976(7) . ?
Cu1 N1 2.064(8) . ?
Cu1 Cl1 2.232(2) . ?
Cu1 Cl2 2.250(3) . ?
O1 C9 1.203(11) . ?
N1 C2 1.344(11) . ?
N1 C6 1.346(12) . ?
N2 C10 1.351(11) . ?
N2 C8 1.403(12) . ?
N3 C9 1.381(13) . ?
N3 C10 1.404(10) . ?
N3 C11 1.422(11) . ?
C2 C3 1.379(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.457(12) . ?
C7 C8 1.325(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.501(12) . ?
C10 Se1 1.832(11) . ?
C11 C12 1.480(14) . ?
C11 C13 1.485(15) . ?
C11 H11 0.78(11) . ?
C12 C13 1.478(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
Se1 C14 1.947(11) . ?
C14 C15 1.510(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.496(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C16 1.525(10) 7_657 ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
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
C6 N1 C2 C3 3.6(15) . . . . ?
Cu1 N1 C2 C3 -167.1(8) . . . . ?
N1 C2 C3 C4 1.8(16) . . . . ?
C2 C3 C4 C5 -5.5(16) . . . . ?
C3 C4 C5 C6 4.0(16) . . . . ?
C2 N1 C6 C5 -5.2(14) . . . . ?
Cu1 N1 C6 C5 165.2(7) . . . . ?
C2 N1 C6 C7 173.8(8) . . . . ?
Cu1 N1 C6 C7 -15.8(12) . . . . ?
C4 C5 C6 N1 1.5(16) . . . . ?
C4 C5 C6 C7 -177.5(9) . . . . ?
N1 C6 C7 C8 -9.1(15) . . . . ?
C5 C6 C7 C8 169.9(10) . . . . ?
C6 C7 C8 N2 2.8(16) . . . . ?
C6 C7 C8 C9 -177.8(8) . . . . ?
C10 N2 C8 C7 -176.1(9) . . . . ?
Cu1 N2 C8 C7 27.0(12) . . . . ?
C10 N2 C8 C9 4.4(10) . . . . ?
Cu1 N2 C8 C9 -152.5(6) . . . . ?
C10 N3 C9 O1 -175.8(9) . . . . ?
C11 N3 C9 O1 0.8(15) . . . . ?
C10 N3 C9 C8 3.6(9) . . . . ?
C11 N3 C9 C8 -179.7(8) . . . . ?
C7 C8 C9 O1 -5.0(16) . . . . ?
N2 C8 C9 O1 174.4(10) . . . . ?
C7 C8 C9 N3 175.5(9) . . . . ?
N2 C8 C9 N3 -5.0(10) . . . . ?
C8 N2 C10 N3 -2.2(10) . . . . ?
Cu1 N2 C10 N3 150.3(6) . . . . ?
C8 N2 C10 Se1 179.8(7) . . . . ?
Cu1 N2 C10 Se1 -27.8(13) . . . . ?
C9 N3 C10 N2 -1.1(10) . . . . ?
C11 N3 C10 N2 -177.7(8) . . . . ?
C9 N3 C10 Se1 177.2(6) . . . . ?
C11 N3 C10 Se1 0.6(12) . . . . ?
C9 N3 C11 C12 52.5(14) . . . . ?
C10 N3 C11 C12 -131.4(11) . . . . ?
C9 N3 C11 C13 123.2(11) . . . . ?
C10 N3 C11 C13 -60.7(14) . . . . ?
N3 C11 C12 C13 111.1(11) . . . . ?
N3 C11 C13 C12 -108.6(12) . . . . ?
N2 C10 Se1 C14 -9.4(10) . . . . ?
N3 C10 Se1 C14 172.6(7) . . . . ?
Se1 C14 C15 C16 139.3(12) . . . . ?
C14 C15 C16 C16 -84(3) . . . 7_657 ?
