#------------------------------------------------------------------------------
#$Date: 2016-03-23 23:36:17 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179508 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/05/4340583.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_4340583
loop_
_publ_author_name
'Filatre-Furcate, Agathe'
'Bellec, Nathalie'
'Jeannin, Olivier'
'Auban-Senzier, Pascale'
'Fourmigué, Marc'
'Vacher, Antoine'
'Lorcy, Dominique'
_publ_section_title
;
 Radical or not radical: compared structures of metal (m = ni, au)
 bis-dithiolene complexes with a thiazole backbone.
;
_journal_issue                   16
_journal_name_full               'Inorganic chemistry'
_journal_page_first              8681
_journal_page_last               8690
_journal_paper_doi               10.1021/ic501293z
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C24 H20 P, C10 H10 N2 Ni S8, 2(C2 H3 N) '
_chemical_formula_sum            'C38 H36 N4 Ni P S8'
_chemical_formula_weight         894.93
_chemical_name_common            '[PPh4)[Ni(Et-thiazdt)2]'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.314(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.2864(15)
_cell_length_b                   7.1977(4)
_cell_length_c                   24.6704(15)
_cell_measurement_reflns_used    7282
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.98
_cell_volume                     4219.5(4)
_computing_cell_refinement       'Bruker SMART, 2006'
_computing_data_collection       'Bruker SMART, 2006'
_computing_data_reduction        'Bruker SAINT, 2006'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17697
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1852.0
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.294
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0612P)²+1.3993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                3932
_reflns_number_total             4844
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic501293z_si_001.cif
_cod_data_source_block           monoanion
_cod_depositor_comments
'Adding full bibliography for 4340582--4340584.cif.'
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4340583
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.60546(10) 0.2964(3) 0.58234(10) 0.0205(5) Uani 1 1 d .
C2 C 0.56391(10) 0.1716(3) 0.57313(10) 0.0196(5) Uani 1 1 d .
C3 C 0.65924(11) 0.0628(4) 0.64523(12) 0.0294(6) Uani 1 1 d .
C4 C 0.70960(11) 0.3531(4) 0.64264(12) 0.0338(6) Uani 1 1 d .
H4A H 0.7355 0.3169 0.6829 0.041 Uiso 1 1 calc R
H4B H 0.6991 0.4816 0.6440 0.041 Uiso 1 1 calc R
C5 C 0.73919(14) 0.3378(5) 0.60179(17) 0.0532(9) Uani 1 1 d .
H5A H 0.7525 0.2131 0.6029 0.080 Uiso 1 1 calc R
H5B H 0.7705 0.4221 0.6152 0.080 Uiso 1 1 calc R
H5C H 0.7133 0.3687 0.5615 0.080 Uiso 1 1 calc R
C6 C 0.54662(11) 0.2275(4) 0.73410(11) 0.0237(5) Uani 1 1 d .
C7 C 0.60457(12) 0.2155(4) 0.76644(13) 0.0339(6) Uani 1 1 d .
H7 H 0.6202 0.1238 0.7955 0.041 Uiso 1 1 calc R
C8 C 0.63901(13) 0.3404(5) 0.75533(15) 0.0443(8) Uani 1 1 d .
H8 H 0.6779 0.3329 0.7771 0.053 Uiso 1 1 calc R
C9 C 0.61611(15) 0.4752(4) 0.71234(15) 0.0411(8) Uani 1 1 d .
H9 H 0.6395 0.5588 0.7052 0.049 Uiso 1 1 calc R
C10 C 0.55857(15) 0.4877(4) 0.67959(14) 0.0368(7) Uani 1 1 d .
H10 H 0.5434 0.5784 0.6502 0.044 Uiso 1 1 calc R
C11 C 0.52326(12) 0.3649(4) 0.69048(12) 0.0282(6) Uani 1 1 d .
H11 H 0.4844 0.3742 0.6689 0.034 Uiso 1 1 calc R
C12 C 0.46081(11) -0.0697(3) 0.68781(11) 0.0224(5) Uani 1 1 d .
C13 C 0.46349(12) -0.0505(4) 0.63297(12) 0.0264(6) Uani 1 1 d .
H13 H 0.4849 0.0442 0.6274 0.032 Uiso 1 1 calc R
C14 C 0.43430(12) -0.1725(4) 0.58670(12) 0.0334(6) Uani 1 1 d .
H14 H 0.4368 -0.1614 0.5503 0.040 Uiso 1 1 calc R
C15 C 0.40156(12) -0.3105(4) 0.59427(12) 0.0337(6) Uani 1 1 d .
H15 H 0.3820 -0.3918 0.5629 0.040 Uiso 1 1 calc R
C16 C 0.39760(12) -0.3287(4) 0.64828(12) 0.0327(6) Uani 1 1 d .
H16 H 0.3749 -0.4206 0.6529 0.039 Uiso 1 1 calc R
C17 C 0.42742(12) -0.2100(4) 0.69508(12) 0.0303(6) Uani 1 1 d .
H17 H 0.4253 -0.2234 0.7316 0.036 Uiso 1 1 calc R
C18 C 0.67646(17) -0.2051(5) 0.46698(18) 0.0599(10) Uani 1 1 d .
C19 C 0.67888(19) -0.1179(6) 0.52144(17) 0.0651(11) Uani 1 1 d .
H19A H 0.6465 -0.1537 0.5274 0.098 Uiso 1 1 calc R
H19B H 0.6794 0.0147 0.5176 0.098 Uiso 1 1 calc R
H19C H 0.7124 -0.1574 0.5552 0.098 Uiso 1 1 calc R
N1 N 0.65876(9) 0.2361(3) 0.62287(9) 0.0251(5) Uani 1 1 d .
N2 N 0.67534(18) -0.2735(6) 0.42497(18) 0.0898(13) Uani 1 1 d .
P1 P 0.5000 0.07826(13) 0.7500 0.0207(2) Uani 1 2 d S
S1 S 0.59128(3) 0.51165(8) 0.54867(3) 0.02279(16) Uani 1 1 d .
S2 S 0.49482(3) 0.21949(8) 0.52788(3) 0.02085(15) Uani 1 1 d .
S3 S 0.59173(3) -0.02892(9) 0.61457(3) 0.02690(17) Uani 1 1 d .
S4 S 0.71417(3) -0.05515(14) 0.69409(4) 0.0478(2) Uani 1 1 d .
Ni1 Ni 0.5000 0.5000 0.5000 0.01767(13) Uani 1 2 d S
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
C2 C1 N1 113.8(2) . .
C2 C1 S1 121.51(18) . .
N1 C1 S1 124.66(19) . .
C1 C2 S2 121.98(18) . .
C1 C2 S3 110.20(17) . .
S2 C2 S3 127.79(15) . .
N1 C3 S4 128.0(2) . .
N1 C3 S3 109.96(19) . .
S4 C3 S3 122.07(18) . .
N1 C4 C5 112.9(2) . .
N1 C4 H4A 109.0 . .
C5 C4 H4A 109.0 . .
N1 C4 H4B 109.0 . .
C5 C4 H4B 109.0 . .
H4A C4 H4B 107.8 . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C7 C6 C11 120.0(2) . .
C7 C6 P1 121.4(2) . .
C11 C6 P1 118.4(2) . .
C8 C7 C6 119.7(3) . .
C8 C7 H7 120.1 . .
C6 C7 H7 120.1 . .
C9 C8 C7 120.3(3) . .
C9 C8 H8 119.8 . .
C7 C8 H8 119.8 . .
C8 C9 C10 120.5(3) . .
C8 C9 H9 119.8 . .
C10 C9 H9 119.8 . .
C9 C10 C11 120.1(3) . .
C9 C10 H10 119.9 . .
C11 C10 H10 119.9 . .
C10 C11 C6 119.3(3) . .
C10 C11 H11 120.3 . .
C6 C11 H11 120.3 . .
C13 C12 C17 119.5(2) . .
C13 C12 P1 121.7(2) . .
C17 C12 P1 118.86(18) . .
C14 C13 C12 119.9(2) . .
C14 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
C15 C14 C13 120.2(2) . .
C15 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
C14 C15 C16 120.4(3) . .
C14 C15 H15 119.8 . .
C16 C15 H15 119.8 . .
C17 C16 C15 119.8(3) . .
C17 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
C16 C17 C12 120.2(2) . .
C16 C17 H17 119.9 . .
C12 C17 H17 119.9 . .
N2 C18 C19 179.1(5) . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C3 N1 C1 114.0(2) . .
C3 N1 C4 122.6(2) . .
C1 N1 C4 123.3(2) . .
C12 P1 C12 106.90(17) . 2_656
C12 P1 C6 111.45(11) . .
C12 P1 C6 110.32(12) 2_656 .
C12 P1 C6 110.32(12) . 2_656
C12 P1 C6 111.44(11) 2_656 2_656
C6 P1 C6 106.46(17) . 2_656
C1 S1 Ni1 101.04(9) . .
C2 S2 Ni1 101.68(9) . .
C3 S3 C2 92.02(13) . .
S2 Ni1 S2 180.0 . 5_666
S2 Ni1 S1 93.74(2) . .
S2 Ni1 S1 86.26(2) 5_666 .
S2 Ni1 S1 86.26(2) . 5_666
S2 Ni1 S1 93.74(2) 5_666 5_666
S1 Ni1 S1 180.0 . 5_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.356(3) .
C1 N1 1.398(3) .
C1 S1 1.722(2) .
C2 S2 1.712(2) .
C2 S3 1.739(2) .
C3 N1 1.362(4) .
C3 S4 1.664(3) .
C3 S3 1.735(3) .
C4 N1 1.475(3) .
C4 C5 1.518(4) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C6 C7 1.388(4) .
C6 C11 1.396(4) .
C6 P1 1.795(2) .
C7 C8 1.384(4) .
C7 H7 0.9300 .
C8 C9 1.372(5) .
C8 H8 0.9300 .
C9 C10 1.380(5) .
C9 H9 0.9300 .
C10 C11 1.388(4) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 C13 1.391(3) .
C12 C17 1.399(4) .
C12 P1 1.788(3) .
C13 C14 1.384(4) .
C13 H13 0.9300 .
C14 C15 1.378(4) .
C14 H14 0.9300 .
C15 C16 1.386(4) .
C15 H15 0.9300 .
C16 C17 1.379(4) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 N2 1.136(5) .
C18 C19 1.459(5) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
P1 C12 1.788(3) 2_656
P1 C6 1.795(2) 2_656
S1 Ni1 2.1778(6) .
S2 Ni1 2.1560(6) .
Ni1 S2 2.1561(6) 5_666
Ni1 S1 2.1779(6) 5_666
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_4
N1 C1 C2 S2 177.06(16) .
S1 C1 C2 S2 -0.3(3) .
N1 C1 C2 S3 -1.3(3) .
S1 C1 C2 S3 -178.69(12) .
C11 C6 C7 C8 0.1(4) .
P1 C6 C7 C8 -176.1(2) .
C6 C7 C8 C9 -0.3(4) .
C7 C8 C9 C10 -0.2(5) .
C8 C9 C10 C11 0.9(4) .
C9 C10 C11 C6 -1.0(4) .
C7 C6 C11 C10 0.5(4) .
P1 C6 C11 C10 176.9(2) .
C17 C12 C13 C14 -1.5(4) .
P1 C12 C13 C14 177.4(2) .
C12 C13 C14 C15 1.5(4) .
C13 C14 C15 C16 -0.1(5) .
C14 C15 C16 C17 -1.1(5) .
C15 C16 C17 C12 1.1(4) .
C13 C12 C17 C16 0.2(4) .
P1 C12 C17 C16 -178.7(2) .
S4 C3 N1 C1 180.0(2) .
S3 C3 N1 C1 0.6(3) .
S4 C3 N1 C4 -3.4(4) .
S3 C3 N1 C4 177.14(19) .
C2 C1 N1 C3 0.5(3) .
S1 C1 N1 C3 177.77(18) .
C2 C1 N1 C4 -176.0(2) .
S1 C1 N1 C4 1.2(3) .
C5 C4 N1 C3 95.5(3) .
C5 C4 N1 C1 -88.2(3) .
C13 C12 P1 C12 -127.1(3) 2_656
C17 C12 P1 C12 51.86(19) 2_656
C13 C12 P1 C6 -6.4(3) .
C17 C12 P1 C6 172.5(2) .
C13 C12 P1 C6 111.6(2) 2_656
C17 C12 P1 C6 -69.5(2) 2_656
C7 C6 P1 C12 -116.4(2) .
C11 C6 P1 C12 67.3(2) .
C7 C6 P1 C12 2.2(3) 2_656
C11 C6 P1 C12 -174.10(19) 2_656
C7 C6 P1 C6 123.2(2) 2_656
C11 C6 P1 C6 -53.04(17) 2_656
C2 C1 S1 Ni1 1.6(2) .
N1 C1 S1 Ni1 -175.43(18) .
C1 C2 S2 Ni1 -1.2(2) .
S3 C2 S2 Ni1 176.87(14) .
N1 C3 S3 C2 -1.12(19) .
S4 C3 S3 C2 179.41(18) .
C1 C2 S3 C3 1.41(19) .
S2 C2 S3 C3 -176.88(17) .
C2 S2 Ni1 S2 40(14) 5_666
C2 S2 Ni1 S1 1.73(8) .
C2 S2 Ni1 S1 -178.27(8) 5_666
C1 S1 Ni1 S2 -1.83(8) .
C1 S1 Ni1 S2 178.17(8) 5_666
C1 S1 Ni1 S1 -87(43) 5_666
