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#$Date: 2023-10-06 03:03:22 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286728 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/73/7247345.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_7247345
loop_
_publ_author_name
'Costa, António G.'
'Lopes, Gonçalo'
'Ribeiro, Susana'
'Santos, Isabel C.'
'Simão, Dulce'
'Pereira, Laura C. J.'
'Le Breton, Nolwenn'
'Choua, Sylvie'
'Baudron, Stéphane A.'
'Almeida, Manuel'
'Rabaça, Sandra'
_publ_section_title
;
 Cyano benzene functionalised Ni and Cu bisdithiolene complexes
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              5362
_journal_page_last               5371
_journal_paper_doi               10.1039/D3CE00782K
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C24 H20 P, C14 H6 N2 Ni S4'
_chemical_formula_sum            'C38 H26 N2 Ni P S4'
_chemical_formula_weight         728.53
_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-2014/7
_audit_update_record
;
2023-07-24 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.3960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.9983(7)
_cell_length_b                   11.6753(3)
_cell_length_c                   11.6640(3)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.83
_cell_measurement_theta_min      2.60
_cell_volume                     3404.20(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            51724
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.003
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       prism
_exptl_crystal_F_000             1500
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0456
_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)+(0.0561P)²+3.5773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1198
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2792
_reflns_number_total             3489
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00782k2.cif
_cod_data_source_block           tppNi3cbdt2
_cod_depositor_comments
'Adding full bibliography for 7247344--7247351.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7247345
_shelx_shelxl_version_number     2014/7
_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   0.842
_shelx_estimated_absorpt_t_max   0.948
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
Ni1 Ni 0.2500 0.2500 0.0000 0.05972(18) Uani 1 2 d S . P . .
S1 S 0.30371(3) 0.37273(8) 0.07694(7) 0.0721(2) Uani 1 1 d . . . . .
S2 S 0.24318(3) 0.15596(7) 0.15677(8) 0.0701(2) Uani 1 1 d . . . . .
P1 P 0.0000 0.61482(7) 0.2500 0.0412(2) Uani 1 2 d S T P . .
N1 N 0.39577(14) 0.5655(3) 0.2357(3) 0.1007(11) Uani 1 1 d . . . . .
C1 C 0.30983(10) 0.3282(2) 0.2175(3) 0.0585(7) Uani 1 1 d . . . . .
C2 C 0.28328(11) 0.2300(3) 0.2545(3) 0.0634(7) Uani 1 1 d . . . . .
C3 C 0.28844(15) 0.1939(3) 0.3682(3) 0.0806(9) Uani 1 1 d . . . . .
H3 H 0.2716 0.1271 0.3922 0.097 Uiso 1 1 calc R U . . .
C4 C 0.31832(17) 0.2566(4) 0.4443(3) 0.0878(11) Uani 1 1 d . . . . .
H4 H 0.3208 0.2328 0.5203 0.105 Uiso 1 1 calc R U . . .
C5 C 0.34487(14) 0.3548(3) 0.4103(3) 0.0784(9) Uani 1 1 d . . . . .
H5 H 0.3648 0.3969 0.4631 0.094 Uiso 1 1 calc R U . . .
C6 C 0.34159(11) 0.3894(3) 0.2986(3) 0.0635(7) Uani 1 1 d . . . . .
C7 C 0.37092(13) 0.4891(3) 0.2636(3) 0.0731(8) Uani 1 1 d . . . . .
C8 C -0.00197(10) 0.7056(2) 0.3745(2) 0.0463(5) Uani 1 1 d . . . . .
C9 C 0.03582(13) 0.7917(3) 0.3839(3) 0.0693(8) Uani 1 1 d . . . . .
H9 H 0.0603 0.8032 0.3255 0.083 Uiso 1 1 calc R U . . .
C10 C 0.03713(15) 0.8601(3) 0.4797(3) 0.0830(10) Uani 1 1 d . . . . .
H10 H 0.0629 0.9172 0.4867 0.100 Uiso 1 1 calc R U . . .
C11 C 0.00001(15) 0.8438(3) 0.5656(3) 0.0729(9) Uani 1 1 d . . . . .
H11 H 0.0010 0.8898 0.6306 0.087 Uiso 1 1 calc R U . . .
C12 C -0.03780(13) 0.7609(3) 0.5553(2) 0.0639(8) Uani 1 1 d . . . . .
H12 H -0.0630 0.7514 0.6128 0.077 Uiso 1 1 calc R U . . .
C13 C -0.03914(11) 0.6902(2) 0.4599(2) 0.0516(6) Uani 1 1 d . . . . .
H13 H -0.0649 0.6330 0.4536 0.062 Uiso 1 1 calc R U . . .
C14 C 0.05811(9) 0.5249(2) 0.2553(2) 0.0443(5) Uani 1 1 d . . . . .
C15 C 0.06338(12) 0.4370(2) 0.1767(2) 0.0608(7) Uani 1 1 d . . . . .
H15 H 0.0360 0.4224 0.1243 0.073 Uiso 1 1 calc R U . . .
C16 C 0.10913(15) 0.3707(3) 0.1758(3) 0.0762(9) Uani 1 1 d . . . . .
H16 H 0.1127 0.3123 0.1222 0.091 Uiso 1 1 calc R U . . .
C17 C 0.14887(13) 0.3906(3) 0.2531(3) 0.0801(10) Uani 1 1 d . . . . .
H17 H 0.1798 0.3464 0.2515 0.096 Uiso 1 1 calc R U . . .
C18 C 0.14383(12) 0.4758(3) 0.3339(3) 0.0781(10) Uani 1 1 d . . . . .
H18 H 0.1709 0.4874 0.3877 0.094 Uiso 1 1 calc R U . . .
C19 C 0.09888(11) 0.5438(2) 0.3353(3) 0.0589(7) Uani 1 1 d . . . . .
H19 H 0.0957 0.6020 0.3893 0.071 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'
P P 0.1023 0.0942 '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'
Ni Ni 0.3393 1.1124 '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
S2 Ni1 S2 180.0 7 . ?
S2 Ni1 S1 92.20(3) 7 7 ?
S2 Ni1 S1 87.80(3) . 7 ?
S2 Ni1 S1 87.80(3) 7 . ?
S2 Ni1 S1 92.20(3) . . ?
S1 Ni1 S1 180.00(4) 7 . ?
C1 S1 Ni1 104.24(11) . . ?
C2 S2 Ni1 104.80(11) . . ?
C14 P1 C14 108.34(16) 2 . ?
C14 P1 C8 110.24(11) 2 . ?
C14 P1 C8 110.12(11) . . ?
C14 P1 C8 110.12(11) 2 2 ?
C14 P1 C8 110.24(11) . 2 ?
C8 P1 C8 107.78(16) . 2 ?
C2 C1 C6 118.1(3) . . ?
C2 C1 S1 120.2(2) . . ?
C6 C1 S1 121.7(2) . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 S2 118.6(3) . . ?
C3 C2 S2 121.4(3) . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.2(4) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 C7 118.9(3) . . ?
C1 C6 C7 120.1(3) . . ?
N1 C7 C6 177.5(4) . . ?
C13 C8 C9 120.0(2) . . ?
C13 C8 P1 121.94(19) . . ?
C9 C8 P1 118.1(2) . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 119.4(3) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C19 119.2(2) . . ?
C15 C14 P1 119.53(19) . . ?
C19 C14 P1 121.2(2) . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 119.5(3) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
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
Ni1 S2 2.1407(9) 7 ?
Ni1 S2 2.1407(9) . ?
Ni1 S1 2.1551(8) 7 ?
Ni1 S1 2.1551(8) . ?
S1 C1 1.725(3) . ?
S2 C2 1.742(3) . ?
P1 C14 1.793(2) 2 ?
P1 C14 1.793(2) . ?
P1 C8 1.798(2) . ?
P1 C8 1.798(2) 2 ?
N1 C7 1.136(5) . ?
C1 C2 1.395(4) . ?
C1 C6 1.424(4) . ?
C2 C3 1.397(5) . ?
C3 C4 1.369(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.436(5) . ?
C8 C13 1.379(3) . ?
C8 C9 1.384(4) . ?
C9 C10 1.373(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.358(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.383(4) . ?
C14 C19 1.395(4) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.357(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(4) . ?
C18 H18 0.9300 . ?
C19 H19 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
Ni1 S1 C1 C2 1.3(2) . . . . ?
Ni1 S1 C1 C6 -178.6(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
S1 C1 C2 C3 179.8(2) . . . . ?
C6 C1 C2 S2 178.7(2) . . . . ?
S1 C1 C2 S2 -1.2(3) . . . . ?
Ni1 S2 C2 C1 0.4(2) . . . . ?
Ni1 S2 C2 C3 179.4(2) . . . . ?
C1 C2 C3 C4 1.9(5) . . . . ?
S2 C2 C3 C4 -177.1(3) . . . . ?
C2 C3 C4 C5 -1.5(6) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 C5 C6 C1 2.1(5) . . . . ?
C4 C5 C6 C7 -177.7(3) . . . . ?
C2 C1 C6 C5 -1.7(4) . . . . ?
S1 C1 C6 C5 178.2(2) . . . . ?
C2 C1 C6 C7 178.2(3) . . . . ?
S1 C1 C6 C7 -1.9(4) . . . . ?
C14 P1 C8 C13 9.9(3) 2 . . . ?
C14 P1 C8 C13 -109.6(2) . . . . ?
C8 P1 C8 C13 130.1(3) 2 . . . ?
C14 P1 C8 C9 -171.1(2) 2 . . . ?
C14 P1 C8 C9 69.4(3) . . . . ?
C8 P1 C8 C9 -50.9(2) 2 . . . ?
C13 C8 C9 C10 1.5(5) . . . . ?
P1 C8 C9 C10 -177.4(3) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C9 C10 C11 C12 -0.3(6) . . . . ?
C10 C11 C12 C13 1.2(5) . . . . ?
C9 C8 C13 C12 -0.7(4) . . . . ?
P1 C8 C13 C12 178.2(2) . . . . ?
C11 C12 C13 C8 -0.7(4) . . . . ?
C14 P1 C14 C15 49.95(19) 2 . . . ?
C8 P1 C14 C15 170.6(2) . . . . ?
C8 P1 C14 C15 -70.6(2) 2 . . . ?
C14 P1 C14 C19 -131.8(2) 2 . . . ?
C8 P1 C14 C19 -11.1(2) . . . . ?
C8 P1 C14 C19 107.7(2) 2 . . . ?
C19 C14 C15 C16 -1.6(4) . . . . ?
P1 C14 C15 C16 176.7(2) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C15 C16 C17 C18 0.9(5) . . . . ?
C16 C17 C18 C19 -1.7(5) . . . . ?
C17 C18 C19 C14 0.9(5) . . . . ?
C15 C14 C19 C18 0.8(4) . . . . ?
P1 C14 C19 C18 -177.5(2) . . . . ?
