#------------------------------------------------------------------------------
#$Date: 2024-12-06 19:44:38 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296482 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/95/7249572.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_7249572
loop_
_publ_author_name
'Gurbanov, Atash V.'
'Mahmoudi, Ghodrat'
'Zangrando, Ennio'
'Zubkov, Fedor I.'
'Hasanov, Khudayar I.'
'Mahmudov, Kamran T.'
_publ_section_title
;
 Bridging linker installation strategy in the engineering of copper(ii)
 complexes: activation of nitriles, efficient catalysts for the
 cyanosilylation of aldehydes
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              6692
_journal_page_last               6700
_journal_paper_doi               10.1039/D4CE00950A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C20 H16 Cu N6 O4 S3 [+ solvent]'
_chemical_formula_sum            'C20 H16 Cu N6 O4 S3'
_chemical_formula_weight         564.11
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2024-08-16 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.633(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.938(4)
_cell_length_b                   30.421(10)
_cell_length_c                   15.066(4)
_cell_measurement_reflns_used    9755
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.09
_cell_measurement_theta_min      2.65
_cell_volume                     5243(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            50955
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.425
_diffrn_reflns_theta_min         2.042
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       needle
_exptl_crystal_F_000             2296
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0582P)²+30.8360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1632
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3987
_reflns_number_total             5376
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00950a2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7249567--7249573.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7249572
_shelx_shelxl_version_number     2019/2
_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   0.754
_shelx_estimated_absorpt_t_max   0.888
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 0.56893(5) 0.62262(2) 0.42359(4) 0.03620(18) Uani 1 1 d . . . . .
S1 S 0.77834(11) 0.65640(4) 0.35819(10) 0.0431(3) Uani 1 1 d . . . . .
S2 S 0.11826(10) 0.75425(4) 0.36484(9) 0.0413(3) Uani 1 1 d . . . . .
S3 S 0.16929(11) 0.81781(4) 0.36331(9) 0.0399(3) Uani 1 1 d . . . . .
O1 O 0.6675(3) 0.66993(11) 0.3718(3) 0.0488(9) Uani 1 1 d . . . . .
O2 O 0.8472(4) 0.69275(14) 0.3428(3) 0.0656(12) Uani 1 1 d . . . . .
O3 O 0.7626(4) 0.62191(14) 0.2897(3) 0.0625(11) Uani 1 1 d . . . . .
O4 O 0.4037(3) 0.50393(12) 0.3244(3) 0.0558(10) Uani 1 1 d . . . . .
N1 N 0.6992(3) 0.58020(12) 0.4526(3) 0.0334(9) Uani 1 1 d . . . . .
N2 N 0.6917(3) 0.53757(12) 0.4538(3) 0.0372(9) Uani 1 1 d . . . . .
N3 N 0.4646(3) 0.57687(13) 0.3515(3) 0.0375(9) Uani 1 1 d . . . . .
H3N H 0.391641 0.587737 0.317073 0.045 Uiso 1 1 d R U . . .
N4 N 0.6188(5) 0.43286(16) 0.4265(5) 0.0789(18) Uani 1 1 d . . . . .
N5 N 0.4335(3) 0.66520(12) 0.3995(3) 0.0365(9) Uani 1 1 d . . . . .
N6 N 0.1229(3) 0.85610(12) 0.0637(3) 0.0341(8) Uani 1 1 d . . . . .
C1 C 0.8148(4) 0.59511(16) 0.4988(4) 0.0383(11) Uani 1 1 d . . . . .
C2 C 0.8582(4) 0.63210(17) 0.4646(4) 0.0425(12) Uani 1 1 d . . . . .
C3 C 0.9662(5) 0.6493(2) 0.5122(5) 0.0681(19) Uani 1 1 d . . . . .
H3 H 0.993913 0.674633 0.491170 0.082 Uiso 1 1 calc R U . . .
C4 C 1.0324(6) 0.6283(3) 0.5912(6) 0.094(3) Uani 1 1 d . . . . .
H4 H 1.104721 0.639793 0.623607 0.113 Uiso 1 1 calc R U . . .
C5 C 0.9924(6) 0.5903(3) 0.6226(6) 0.093(3) Uani 1 1 d . . . . .
H5 H 1.039419 0.575545 0.673982 0.111 Uiso 1 1 calc R U . . .
C6 C 0.8836(5) 0.5744(2) 0.5781(4) 0.0591(16) Uani 1 1 d . . . . .
H6 H 0.855496 0.549625 0.600851 0.071 Uiso 1 1 calc R U . . .
C7 C 0.5928(5) 0.51647(15) 0.4139(4) 0.0410(12) Uani 1 1 d . . . . .
C8 C 0.4816(4) 0.53538(16) 0.3623(4) 0.0392(11) Uani 1 1 d . . . . .
C9 C 0.6053(5) 0.46992(18) 0.4210(4) 0.0536(14) Uani 1 1 d . . . . .
C10 C 0.2844(5) 0.5171(2) 0.2801(5) 0.0671(18) Uani 1 1 d . . . . .
H10A H 0.238087 0.491595 0.256481 0.101 Uiso 1 1 calc R U . . .
H10B H 0.282570 0.536849 0.230010 0.101 Uiso 1 1 calc R U . . .
H10C H 0.253198 0.531621 0.324432 0.101 Uiso 1 1 calc R U . . .
C11 C 0.3354(5) 0.65258(17) 0.4177(4) 0.0420(12) Uani 1 1 d . . . . .
H11 H 0.331184 0.623988 0.438312 0.050 Uiso 1 1 calc R U . . .
C12 C 0.2401(4) 0.67946(16) 0.4075(3) 0.0385(11) Uani 1 1 d . . . . .
H12 H 0.172778 0.669022 0.419624 0.046 Uiso 1 1 calc R U . . .
C13 C 0.2464(4) 0.72254(16) 0.3789(3) 0.0365(10) Uani 1 1 d . . . . .
C14 C 0.3472(4) 0.73586(16) 0.3591(4) 0.0395(11) Uani 1 1 d . . . . .
H14 H 0.353543 0.764314 0.338475 0.047 Uiso 1 1 calc R U . . .
C15 C 0.4379(4) 0.70666(16) 0.3701(4) 0.0400(11) Uani 1 1 d . . . . .
H15 H 0.505326 0.716013 0.356541 0.048 Uiso 1 1 calc R U . . .
C16 C 0.1533(4) 0.82984(15) 0.2450(3) 0.0318(10) Uani 1 1 d . . . . .
C17 C 0.1529(4) 0.79918(15) 0.1777(3) 0.0345(10) Uani 1 1 d . . . . .
H17 H 0.163138 0.769453 0.192113 0.041 Uiso 1 1 calc R U . . .
C18 C 0.1368(4) 0.81373(15) 0.0882(3) 0.0359(10) Uani 1 1 d . . . . .
H18 H 0.135441 0.793008 0.042545 0.043 Uiso 1 1 calc R U . . .
C19 C 0.1286(4) 0.88533(15) 0.1307(4) 0.0397(11) Uani 1 1 d . . . . .
H19 H 0.123247 0.915008 0.115277 0.048 Uiso 1 1 calc R U . . .
C20 C 0.1420(4) 0.87388(15) 0.2220(4) 0.0378(11) Uani 1 1 d . . . . .
H20 H 0.143354 0.895194 0.266559 0.045 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'
S S 0.1246 0.1234 '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'
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
N1 Cu1 N3 89.64(16) . . ?
N1 Cu1 N5 177.20(17) . . ?
N3 Cu1 N5 90.41(16) . . ?
N1 Cu1 N6 89.03(15) . 8_566 ?
N3 Cu1 N6 136.60(17) . 8_566 ?
N5 Cu1 N6 89.01(15) . 8_566 ?
N1 Cu1 O1 92.28(15) . . ?
N3 Cu1 O1 126.79(17) . . ?
N5 Cu1 O1 89.92(15) . . ?
N6 Cu1 O1 96.60(16) 8_566 . ?
O2 S1 O3 114.0(3) . . ?
O2 S1 O1 113.0(2) . . ?
O3 S1 O1 111.6(3) . . ?
O2 S1 C2 106.4(3) . . ?
O3 S1 C2 105.6(3) . . ?
O1 S1 C2 105.4(2) . . ?
C13 S2 S3 105.60(17) . . ?
C16 S3 S2 105.16(16) . . ?
S1 O1 Cu1 118.5(2) . . ?
C8 O4 C10 118.0(4) . . ?
N2 N1 C1 111.7(4) . . ?
N2 N1 Cu1 127.1(3) . . ?
C1 N1 Cu1 119.4(3) . . ?
N1 N2 C7 122.1(4) . . ?
C8 N3 Cu1 125.0(3) . . ?
C8 N3 H3N 120.4 . . ?
Cu1 N3 H3N 113.3 . . ?
C11 N5 C15 117.2(4) . . ?
C11 N5 Cu1 118.9(3) . . ?
C15 N5 Cu1 123.8(3) . . ?
C19 N6 C18 117.2(4) . . ?
C19 N6 Cu1 119.0(3) . 8_465 ?
C18 N6 Cu1 123.1(3) . 8_465 ?
C6 C1 C2 119.4(5) . . ?
C6 C1 N1 121.6(5) . . ?
C2 C1 N1 119.0(4) . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 S1 119.3(5) . . ?
C1 C2 S1 120.5(4) . . ?
C4 C3 C2 119.3(6) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.8(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.9(7) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.4(6) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N2 C7 C9 112.7(5) . . ?
N2 C7 C8 127.6(4) . . ?
C9 C7 C8 119.6(5) . . ?
N3 C8 O4 125.7(5) . . ?
N3 C8 C7 123.1(4) . . ?
O4 C8 C7 111.2(4) . . ?
N4 C9 C7 177.8(7) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 C12 123.6(5) . . ?
N5 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C13 118.7(5) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 118.2(4) . . ?
C14 C13 S2 126.2(4) . . ?
C12 C13 S2 115.5(4) . . ?
C15 C14 C13 119.3(5) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
N5 C15 C14 122.9(5) . . ?
N5 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C17 C16 C20 119.5(4) . . ?
C17 C16 S3 125.2(4) . . ?
C20 C16 S3 115.3(4) . . ?
C16 C17 C18 118.2(4) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
N6 C18 C17 123.5(4) . . ?
N6 C18 H18 118.3 . . ?
C17 C18 H18 118.3 . . ?
N6 C19 C20 123.5(4) . . ?
N6 C19 H19 118.2 . . ?
C20 C19 H19 118.2 . . ?
C16 C20 C19 118.0(4) . . ?
C16 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
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 N1 1.971(4) . ?
Cu1 N3 1.973(4) . ?
Cu1 N5 2.022(4) . ?
Cu1 N6 2.123(4) 8_566 ?
Cu1 O1 2.143(4) . ?
S1 O2 1.436(4) . ?
S1 O3 1.446(4) . ?
S1 O1 1.455(4) . ?
S1 C2 1.775(6) . ?
S2 C13 1.769(5) . ?
S2 S3 2.0292(19) . ?
S3 C16 1.775(5) . ?
O4 C8 1.342(6) . ?
O4 C10 1.446(7) . ?
N1 N2 1.300(5) . ?
N1 C1 1.430(6) . ?
N2 C7 1.328(6) . ?
N3 C8 1.281(6) . ?
N3 H3N 0.9374 . ?
N4 C9 1.139(7) . ?
N5 C11 1.334(7) . ?
N5 C15 1.343(6) . ?
N6 C19 1.333(6) . ?
N6 C18 1.338(6) . ?
C1 C6 1.392(7) . ?
C1 C2 1.397(7) . ?
C2 C3 1.386(8) . ?
C3 C4 1.382(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C9 1.425(7) . ?
C7 C8 1.451(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.373(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(7) . ?
C14 C15 1.374(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.378(7) . ?
C16 C20 1.381(6) . ?
C17 C18 1.379(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.383(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
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
O2 S1 O1 Cu1 -167.4(3) . . . . ?
O3 S1 O1 Cu1 62.6(3) . . . . ?
C2 S1 O1 Cu1 -51.6(3) . . . . ?
C1 N1 N2 C7 -179.0(5) . . . . ?
Cu1 N1 N2 C7 16.6(7) . . . . ?
N2 N1 C1 C6 -37.0(7) . . . . ?
Cu1 N1 C1 C6 128.7(5) . . . . ?
N2 N1 C1 C2 144.7(5) . . . . ?
Cu1 N1 C1 C2 -49.5(6) . . . . ?
C6 C1 C2 C3 -3.4(9) . . . . ?
N1 C1 C2 C3 174.9(5) . . . . ?
C6 C1 C2 S1 174.4(5) . . . . ?
N1 C1 C2 S1 -7.3(7) . . . . ?
O2 S1 C2 C3 -1.4(6) . . . . ?
O3 S1 C2 C3 120.2(5) . . . . ?
O1 S1 C2 C3 -121.5(5) . . . . ?
O2 S1 C2 C1 -179.1(4) . . . . ?
O3 S1 C2 C1 -57.6(5) . . . . ?
O1 S1 C2 C1 60.7(5) . . . . ?
C1 C2 C3 C4 2.8(11) . . . . ?
S1 C2 C3 C4 -174.9(7) . . . . ?
C2 C3 C4 C5 0.5(14) . . . . ?
C3 C4 C5 C6 -3.4(15) . . . . ?
C4 C5 C6 C1 2.8(13) . . . . ?
C2 C1 C6 C5 0.5(10) . . . . ?
N1 C1 C6 C5 -177.7(7) . . . . ?
N1 N2 C7 C9 178.1(5) . . . . ?
N1 N2 C7 C8 1.6(9) . . . . ?
Cu1 N3 C8 O4 169.1(4) . . . . ?
Cu1 N3 C8 C7 -14.8(7) . . . . ?
C10 O4 C8 N3 -10.9(8) . . . . ?
C10 O4 C8 C7 172.7(5) . . . . ?
N2 C7 C8 N3 -2.4(9) . . . . ?
C9 C7 C8 N3 -178.6(5) . . . . ?
N2 C7 C8 O4 174.2(5) . . . . ?
C9 C7 C8 O4 -2.0(7) . . . . ?
C15 N5 C11 C12 0.2(7) . . . . ?
Cu1 N5 C11 C12 177.2(4) . . . . ?
N5 C11 C12 C13 -1.5(8) . . . . ?
C11 C12 C13 C14 2.0(7) . . . . ?
C11 C12 C13 S2 178.4(4) . . . . ?
S3 S2 C13 C14 -21.2(5) . . . . ?
S3 S2 C13 C12 162.7(3) . . . . ?
C12 C13 C14 C15 -1.3(7) . . . . ?
S2 C13 C14 C15 -177.3(4) . . . . ?
C11 N5 C15 C14 0.5(7) . . . . ?
Cu1 N5 C15 C14 -176.3(4) . . . . ?
C13 C14 C15 N5 0.0(8) . . . . ?
S2 S3 C16 C17 -23.1(4) . . . . ?
S2 S3 C16 C20 157.7(3) . . . . ?
C20 C16 C17 C18 -2.3(7) . . . . ?
S3 C16 C17 C18 178.5(4) . . . . ?
C19 N6 C18 C17 1.9(7) . . . . ?
Cu1 N6 C18 C17 -168.9(3) 8_465 . . . ?
C16 C17 C18 N6 0.8(7) . . . . ?
C18 N6 C19 C20 -3.3(7) . . . . ?
Cu1 N6 C19 C20 168.0(4) 8_465 . . . ?
C17 C16 C20 C19 1.1(7) . . . . ?
S3 C16 C20 C19 -179.6(4) . . . . ?
N6 C19 C20 C16 1.8(7) . . . . ?
