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#$Date: 2020-11-06 13:56:04 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258783 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/55/7705525.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_7705525
loop_
_publ_author_name
'Guk, Dmitry'
'Naumov, Alexei'
'Krasnovskaya, Olga'
'Tafeenko, Viktor'
'Moiseeeva, Anna'
'Pergushov, Vladimir'
'Melnikov, Michail'
'Zyk, Nikolai'
'Majouga, Alexander'
'Belolglazkina, Elena'
_publ_section_title
;
 Three types of copper derivatives formed by
 CuCl₂·2H₂O interaction with
 (Z)-3-aryl-2-(methylthio)-5-(pyridine-2-ylmethylene)-3,5-dihydro-4H-imidazol-4-ones.
;
_journal_issue                   41
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14528
_journal_page_last               14535
_journal_paper_doi               10.1039/d0dt02817g
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C16 H12 Cl Cu F N3 O S'
_chemical_formula_sum            'C16 H12 Cl Cu F N3 O S'
_chemical_formula_weight         412.34
_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
;
2020-05-10 deposited with the CCDC.	2020-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.2410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.4118(8)
_cell_length_b                   9.2731(3)
_cell_length_c                   13.7925(5)
_cell_measurement_reflns_used    3542
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      67.8
_cell_measurement_theta_min      5.6
_cell_volume                     3386.98(19)
_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 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  STOE
_diffrn_measurement_method       'rotation method'
_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  0.0844
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17508
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.805
_diffrn_reflns_theta_min         3.338
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    4.593
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_correction_T_min  0.449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_description       plate
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          .24
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .14
_refine_diff_density_max         1.031
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.348
_refine_ls_extinction_coef       0.00142(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0868P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1460
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2031
_reflns_number_total             3095
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt02817g2.cif
_cod_data_source_block           shelx_2fse
_cod_depositor_comments
'Adding full bibliography for 7705524--7705528.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7705525
_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 0.48694(3) 0.51600(6) 0.63069(5) 0.0498(3) Uani 1 1 d . . . . .
Cl1 Cl 0.43286(4) 0.34125(10) 0.59893(9) 0.0550(3) Uani 1 1 d . . . . .
S1 S 0.61998(5) 0.37336(12) 0.67024(11) 0.0616(4) Uani 1 1 d . . . . .
O1 O 0.62671(12) 0.9019(3) 0.6476(3) 0.0614(9) Uani 1 1 d . . . . .
N1 N 0.44660(14) 0.7107(3) 0.6139(3) 0.0454(8) Uani 1 1 d . . . . .
N2 N 0.55260(13) 0.5965(3) 0.6459(2) 0.0434(8) Uani 1 1 d . . . . .
N3 N 0.63256(14) 0.6541(3) 0.6664(3) 0.0472(9) Uani 1 1 d . . . . .
F1 F 0.70858(14) 0.6086(6) 0.8531(3) 0.1191(15) Uani 1 1 d . . . . .
C2 C 0.39777(18) 0.7073(5) 0.5990(4) 0.0527(11) Uani 1 1 d . . . . .
H2 H 0.382891 0.617818 0.598468 0.063 Uiso 1 1 calc R U . . .
C3 C 0.36812(19) 0.8268(5) 0.5844(4) 0.0602(13) Uani 1 1 d . . . . .
H3 H 0.334016 0.818797 0.574083 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3899(2) 0.9596(5) 0.5853(4) 0.0656(14) Uani 1 1 d . . . . .
H4 H 0.370545 1.043089 0.575262 0.079 Uiso 1 1 calc R U . . .
C5 C 0.4402(2) 0.9677(5) 0.6010(4) 0.0568(12) Uani 1 1 d . . . . .
H5 H 0.455540 1.056673 0.602556 0.068 Uiso 1 1 calc R U . . .
C6 C 0.46796(17) 0.8409(4) 0.6146(3) 0.0438(10) Uani 1 1 d . . . . .
C7 C 0.52095(17) 0.8499(4) 0.6279(3) 0.0470(11) Uani 1 1 d . . . . .
H7 H 0.532733 0.943539 0.628153 0.056 Uiso 1 1 calc R U . . .
C8 C 0.55595(16) 0.7477(4) 0.6398(3) 0.0416(9) Uani 1 1 d . . . . .
C9 C 0.60812(17) 0.7861(4) 0.6503(3) 0.0482(11) Uani 1 1 d . . . . .
C10 C 0.59787(18) 0.5476(4) 0.6601(3) 0.0465(10) Uani 1 1 d . . . . .
C11 C 0.68382(17) 0.6308(5) 0.6732(4) 0.0540(12) Uani 1 1 d . . . . .
C12 C 0.6959(2) 0.6287(6) 0.5847(4) 0.0716(15) Uani 1 1 d . . . . .
H12 H 0.671005 0.642995 0.519523 0.086 Uiso 1 1 calc R U . . .
C13 C 0.7452(2) 0.6052(7) 0.5941(5) 0.0851(17) Uani 1 1 d . . . . .
H13 H 0.753801 0.605606 0.535182 0.102 Uiso 1 1 calc R U . . .
C14 C 0.7817(2) 0.5812(7) 0.6900(5) 0.0854(18) Uani 1 1 d . . . . .
H14 H 0.814709 0.562729 0.695453 0.103 Uiso 1 1 calc R U . . .
C15 C 0.7699(2) 0.5842(8) 0.7773(5) 0.0878(19) Uani 1 1 d . . . . .
H15 H 0.794708 0.569534 0.842465 0.105 Uiso 1 1 calc R U . . .
C16 C 0.7212(2) 0.6089(6) 0.7675(4) 0.0713(15) Uani 1 1 d . . . . .
C17 C 0.5659(2) 0.2631(5) 0.6494(4) 0.0657(14) Uani 1 1 d . . . . .
H17A H 0.553521 0.277894 0.704773 0.099 Uiso 1 1 calc R U . . .
H17B H 0.574972 0.163616 0.647848 0.099 Uiso 1 1 calc R U . . .
H17C H 0.540111 0.288313 0.584281 0.099 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'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 '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 98.33(14) . . ?
N2 Cu1 Cl1 152.83(10) . . ?
N1 Cu1 Cl1 107.54(11) . . ?
C10 S1 C17 105.0(2) . . ?
C2 N1 C6 117.7(3) . . ?
C2 N1 Cu1 119.6(3) . . ?
C6 N1 Cu1 122.7(3) . . ?
C10 N2 C8 105.6(4) . . ?
C10 N2 Cu1 137.2(3) . . ?
C8 N2 Cu1 117.2(3) . . ?
C10 N3 C9 108.5(4) . . ?
C10 N3 C11 125.5(3) . . ?
C9 N3 C11 125.4(3) . . ?
N1 C2 C3 124.0(4) . . ?
N1 C2 H2 118.0 . . ?
C3 C2 H2 118.0 . . ?
C2 C3 C4 118.4(5) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 119.0(4) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
N1 C6 C5 121.6(4) . . ?
N1 C6 C7 119.7(3) . . ?
C5 C6 C7 118.7(4) . . ?
C8 C7 C6 131.6(4) . . ?
C8 C7 H7 114.2 . . ?
C6 C7 H7 114.2 . . ?
C7 C8 N2 130.4(4) . . ?
C7 C8 C9 120.9(4) . . ?
N2 C8 C9 108.7(3) . . ?
O1 C9 N3 126.4(4) . . ?
O1 C9 C8 130.3(4) . . ?
N3 C9 C8 103.3(3) . . ?
N2 C10 N3 113.8(4) . . ?
N2 C10 S1 130.3(3) . . ?
N3 C10 S1 115.9(3) . . ?
C16 C11 C12 118.9(5) . . ?
C16 C11 N3 120.2(5) . . ?
C12 C11 N3 120.9(4) . . ?
C13 C12 C11 119.2(5) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 120.3(6) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.5(6) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 118.9(5) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
F1 C16 C15 119.7(5) . . ?
F1 C16 C11 118.1(5) . . ?
C15 C16 C11 122.1(5) . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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 1.949(4) . ?
Cu1 N1 2.106(3) . ?
Cu1 Cl1 2.1658(12) . ?
S1 C10 1.721(4) . ?
S1 C17 1.780(5) . ?
O1 C9 1.203(5) . ?
N1 C2 1.327(6) . ?
N1 C6 1.349(5) . ?
N2 C10 1.310(5) . ?
N2 C8 1.410(5) . ?
N3 C10 1.376(6) . ?
N3 C9 1.385(5) . ?
N3 C11 1.441(6) . ?
F1 C16 1.353(6) . ?
C2 C3 1.362(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.452(6) . ?
C7 C8 1.340(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.480(6) . ?
C11 C16 1.365(7) . ?
C11 C12 1.382(7) . ?
C12 C13 1.376(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(8) . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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
C2 H2 Cl1 0.93 2.93 3.538(4) 124.2 .
C5 H5 Cl1 0.93 2.71 3.469(4) 139.1 1_565
C12 H12 Cl1 0.93 2.81 3.628(6) 147.1 5_666
C17 H17A Cl1 0.96 2.66 3.534(5) 151.9 2_656
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 0.0(7) . . . . ?
Cu1 N1 C2 C3 -178.1(4) . . . . ?
N1 C2 C3 C4 -0.1(8) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C2 N1 C6 C5 0.5(6) . . . . ?
Cu1 N1 C6 C5 178.5(3) . . . . ?
C2 N1 C6 C7 -178.4(4) . . . . ?
Cu1 N1 C6 C7 -0.3(6) . . . . ?
C4 C5 C6 N1 -0.8(7) . . . . ?
C4 C5 C6 C7 178.0(4) . . . . ?
N1 C6 C7 C8 0.6(7) . . . . ?
C5 C6 C7 C8 -178.2(5) . . . . ?
C6 C7 C8 N2 -1.8(8) . . . . ?
C6 C7 C8 C9 179.0(4) . . . . ?
C10 N2 C8 C7 -178.5(4) . . . . ?
Cu1 N2 C8 C7 2.2(6) . . . . ?
C10 N2 C8 C9 0.8(4) . . . . ?
Cu1 N2 C8 C9 -178.5(2) . . . . ?
C10 N3 C9 O1 -177.8(4) . . . . ?
C11 N3 C9 O1 -6.1(7) . . . . ?
C10 N3 C9 C8 3.1(4) . . . . ?
C11 N3 C9 C8 174.8(4) . . . . ?
C7 C8 C9 O1 -2.1(7) . . . . ?
N2 C8 C9 O1 178.5(4) . . . . ?
C7 C8 C9 N3 176.9(4) . . . . ?
N2 C8 C9 N3 -2.4(4) . . . . ?
C8 N2 C10 N3 1.3(5) . . . . ?
Cu1 N2 C10 N3 -179.7(3) . . . . ?
C8 N2 C10 S1 -177.9(3) . . . . ?
Cu1 N2 C10 S1 1.2(7) . . . . ?
C9 N3 C10 N2 -3.0(5) . . . . ?
C11 N3 C10 N2 -174.6(4) . . . . ?
C9 N3 C10 S1 176.3(3) . . . . ?
C11 N3 C10 S1 4.6(6) . . . . ?
C17 S1 C10 N2 3.4(5) . . . . ?
C17 S1 C10 N3 -175.7(3) . . . . ?
C10 N3 C11 C16 -86.3(6) . . . . ?
C9 N3 C11 C16 103.5(6) . . . . ?
C10 N3 C11 C12 93.1(6) . . . . ?
C9 N3 C11 C12 -77.2(6) . . . . ?
C16 C11 C12 C13 -0.2(8) . . . . ?
N3 C11 C12 C13 -179.6(5) . . . . ?
C11 C12 C13 C14 1.3(10) . . . . ?
C12 C13 C14 C15 -1.8(11) . . . . ?
C13 C14 C15 C16 1.1(11) . . . . ?
C14 C15 C16 F1 178.3(6) . . . . ?
C14 C15 C16 C11 0.1(11) . . . . ?
C12 C11 C16 F1 -178.8(5) . . . . ?
N3 C11 C16 F1 0.6(7) . . . . ?
C12 C11 C16 C15 -0.5(9) . . . . ?
N3 C11 C16 C15 178.9(6) . . . . ?
