#------------------------------------------------------------------------------
#$Date: 2016-02-04 02:35:36 +0200 (Thu, 04 Feb 2016) $
#$Revision: 175573 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/46/4344694.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_4344694
loop_
_publ_author_name
'Mebrouk, Kenny'
'Camerel, Franck'
'Jeannin, Olivier'
'Heinrich, Benoit'
'Donnio, Bertrand'
'Fourmigué, Marc'
_publ_section_title
;
 High Photothermal Activity within Neutral Nickel Dithiolene Complexes
 Derived from Imidazolium-Based Ionic Liquids.
;
_journal_issue                   3
_journal_name_full               'Inorganic chemistry'
_journal_page_first              1296
_journal_page_last               1303
_journal_paper_doi               10.1021/acs.inorgchem.5b02648
_journal_volume                  55
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H36 N4 Ni1 S6'
_chemical_formula_sum            'C22 H36 N4 Ni S6'
_chemical_formula_weight         607.62
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-12-14T15:52:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 96.936(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.0192(10)
_cell_length_b                   5.1084(3)
_cell_length_c                   21.3364(16)
_cell_measurement_reflns_used    3747
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.63
_cell_measurement_wavelength     0.71073
_cell_volume                     1408.64(17)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_orient_matrix_type       'by SAINT Bruker-AXS'
_diffrn_orient_matrix_UB_11      0.074804
_diffrn_orient_matrix_UB_12      0.01156
_diffrn_orient_matrix_UB_13      0.017172
_diffrn_orient_matrix_UB_21      0.01971
_diffrn_orient_matrix_UB_22      -0.027081
_diffrn_orient_matrix_UB_23      -0.043404
_diffrn_orient_matrix_UB_31      -0.00171
_diffrn_orient_matrix_UB_32      0.193527
_diffrn_orient_matrix_UB_33      -0.007099
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_laue_measured_fraction_full 0.994
_diffrn_reflns_laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11348
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.632
_diffrn_reflns_theta_min         3.152
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.152
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.22
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     153
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0908P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.128
_refine_ls_wR_factor_ref         0.1533
_reflns_Friedel_coverage         0
_reflns_number_gt                2400
_reflns_number_total             3245
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic5b02648_si_001.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4344694
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.8208(2) 0.3472(7) 1.01258(15) 0.0227(7) Uani 1 1 d . . .
C2 C 0.8912(3) 0.4143(7) 1.06506(15) 0.0231(7) Uani 1 1 d . . .
C3 C 0.7489(3) 0.6650(7) 1.06664(16) 0.0261(7) Uani 1 1 d . . .
C4 C 0.6387(3) 0.4826(7) 0.97160(17) 0.0267(7) Uani 1 1 d . . .
H4A H 0.5814 0.5397 0.9933 0.032 Uiso 1 1 calc R U .
H4B H 0.6271 0.3003 0.9602 0.032 Uiso 1 1 calc R U .
C5 C 0.6390(3) 0.6421(7) 0.91175(16) 0.0286(8) Uani 1 1 d . . .
H5A H 0.6948 0.5823 0.8891 0.034 Uiso 1 1 calc R U .
H5B H 0.6518 0.8243 0.9229 0.034 Uiso 1 1 calc R U .
C6 C 0.5373(3) 0.6204(7) 0.86886(17) 0.0319(8) Uani 1 1 d . . .
H6A H 0.5277 0.4404 0.8549 0.038 Uiso 1 1 calc R U .
H6B H 0.481 0.6643 0.8929 0.038 Uiso 1 1 calc R U .
C7 C 0.5317(3) 0.7967(8) 0.81157(19) 0.0422(10) Uani 1 1 d . . .
H7A H 0.5403 0.9756 0.825 0.063 Uiso 1 1 calc R U .
H7B H 0.4657 0.776 0.7867 0.063 Uiso 1 1 calc R U .
H7C H 0.5857 0.7503 0.7867 0.063 Uiso 1 1 calc R U .
C8 C 0.8906(3) 0.7171(7) 1.15795(16) 0.0287(8) Uani 1 1 d . . .
H8A H 0.8534 0.8755 1.1662 0.034 Uiso 1 1 calc R U .
H8B H 0.9621 0.7642 1.1554 0.034 Uiso 1 1 calc R U .
C9 C 0.8861(3) 0.5269(7) 1.21247(16) 0.0286(8) Uani 1 1 d . . .
H9A H 0.9278 0.3747 1.2054 0.034 Uiso 1 1 calc R U .
H9B H 0.9169 0.6102 1.2511 0.034 Uiso 1 1 calc R U .
C10 C 0.7782(3) 0.4360(8) 1.22160(18) 0.0346(8) Uani 1 1 d . . .
H10A H 0.7479 0.3457 1.1838 0.042 Uiso 1 1 calc R U .
H10B H 0.7354 0.5872 1.2277 0.042 Uiso 1 1 calc R U .
C11 C 0.7792(4) 0.2532(10) 1.27825(19) 0.0472(11) Uani 1 1 d . . .
H11A H 0.819 0.0997 1.2715 0.071 Uiso 1 1 calc R U .
H11B H 0.7096 0.2032 1.2833 0.071 Uiso 1 1 calc R U .
H11C H 0.8097 0.3416 1.3156 0.071 Uiso 1 1 calc R U .
N1 N 0.7341(2) 0.5023(5) 1.01497(13) 0.0231(6) Uani 1 1 d . . .
N2 N 0.8458(2) 0.6070(6) 1.09728(13) 0.0240(6) Uani 1 1 d . . .
S1 S 0.84606(6) 0.11851(17) 0.96009(4) 0.0239(2) Uani 1 1 d . . .
S2 S 1.00844(6) 0.27067(17) 1.07926(4) 0.0235(2) Uani 1 1 d . . .
S3 S 0.66598(7) 0.88764(19) 1.08730(4) 0.0330(3) Uani 1 1 d . . .
Ni1 Ni 1 0 1 0.02100(19) Uani 1 2 d S . P
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 0 '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'
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
N1 C1 C2 106.7(3) . .
N1 C1 S1 130.5(3) . .
C2 C1 S1 122.8(3) . .
N2 C2 C1 107.2(3) . .
N2 C2 S2 131.0(3) . .
C1 C2 S2 121.8(3) . .
N1 C3 N2 106.4(3) . .
N1 C3 S3 126.3(3) . .
N2 C3 S3 127.3(3) . .
N1 C4 C5 114.1(3) . .
N1 C4 H4A 108.7 . .
C5 C4 H4A 108.7 . .
N1 C4 H4B 108.7 . .
C5 C4 H4B 108.7 . .
H4A C4 H4B 107.6 . .
C4 C5 C6 112.2(3) . .
C4 C5 H5A 109.2 . .
C6 C5 H5A 109.2 . .
C4 C5 H5B 109.2 . .
C6 C5 H5B 109.2 . .
H5A C5 H5B 107.9 . .
C7 C6 C5 113.4(3) . .
C7 C6 H6A 108.9 . .
C5 C6 H6A 108.9 . .
C7 C6 H6B 108.9 . .
C5 C6 H6B 108.9 . .
H6A C6 H6B 107.7 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N2 C8 C9 112.5(3) . .
N2 C8 H8A 109.1 . .
C9 C8 H8A 109.1 . .
N2 C8 H8B 109.1 . .
C9 C8 H8B 109.1 . .
H8A C8 H8B 107.8 . .
C10 C9 C8 114.6(3) . .
C10 C9 H9A 108.6 . .
C8 C9 H9A 108.6 . .
C10 C9 H9B 108.6 . .
C8 C9 H9B 108.6 . .
H9A C9 H9B 107.6 . .
C9 C10 C11 111.7(3) . .
C9 C10 H10A 109.3 . .
C11 C10 H10A 109.3 . .
C9 C10 H10B 109.3 . .
C11 C10 H10B 109.3 . .
H10A C10 H10B 107.9 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C3 N1 C1 109.8(3) . .
C3 N1 C4 125.2(3) . .
C1 N1 C4 124.9(3) . .
C2 N2 C3 109.9(3) . .
C2 N2 C8 124.5(3) . .
C3 N2 C8 125.4(3) . .
C1 S1 Ni1 100.30(12) . .
C2 S2 Ni1 100.20(12) . .
S1 Ni1 S1 180 . 3_757
S1 Ni1 S2 94.89(3) . .
S1 Ni1 S2 85.11(3) 3_757 .
S1 Ni1 S2 85.11(3) . 3_757
S1 Ni1 S2 94.89(3) 3_757 3_757
S2 Ni1 S2 180 . 3_757
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.385(4) .
C1 C2 1.401(5) .
C1 S1 1.678(3) .
C2 N2 1.374(4) .
C2 S2 1.688(4) .
C3 N1 1.376(5) .
C3 N2 1.380(4) .
C3 S3 1.664(3) .
C4 N1 1.460(4) .
C4 C5 1.515(5) .
C4 H4A 0.97 .
C4 H4B 0.97 .
C5 C6 1.520(5) .
C5 H5A 0.97 .
C5 H5B 0.97 .
C6 C7 1.513(5) .
C6 H6A 0.97 .
C6 H6B 0.97 .
C7 H7A 0.96 .
C7 H7B 0.96 .
C7 H7C 0.96 .
C8 N2 1.466(4) .
C8 C9 1.522(5) .
C8 H8A 0.97 .
C8 H8B 0.97 .
C9 C10 1.514(5) .
C9 H9A 0.97 .
C9 H9B 0.97 .
C10 C11 1.526(5) .
C10 H10A 0.97 .
C10 H10B 0.97 .
C11 H11A 0.96 .
C11 H11B 0.96 .
C11 H11C 0.96 .
S1 Ni1 2.1671(8) .
S2 Ni1 2.1769(8) .
Ni1 S1 2.1671(8) 3_757
Ni1 S2 2.1769(8) 3_757
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
N1 C1 C2 N2 -0.2(4)
S1 C1 C2 N2 179.7(2)
N1 C1 C2 S2 -179.4(2)
S1 C1 C2 S2 0.6(4)
N1 C4 C5 C6 -178.7(3)
C4 C5 C6 C7 174.8(3)
N2 C8 C9 C10 -58.5(4)
C8 C9 C10 C11 -178.1(3)
N2 C3 N1 C1 -0.9(3)
S3 C3 N1 C1 178.9(2)
N2 C3 N1 C4 175.2(3)
S3 C3 N1 C4 -5.1(5)
C2 C1 N1 C3 0.7(4)
S1 C1 N1 C3 -179.3(3)
C2 C1 N1 C4 -175.4(3)
S1 C1 N1 C4 4.7(5)
C5 C4 N1 C3 97.7(4)
C5 C4 N1 C1 -86.8(4)
C1 C2 N2 C3 -0.3(4)
S2 C2 N2 C3 178.7(3)
C1 C2 N2 C8 174.9(3)
S2 C2 N2 C8 -6.0(5)
N1 C3 N2 C2 0.7(4)
S3 C3 N2 C2 -179.0(3)
N1 C3 N2 C8 -174.4(3)
S3 C3 N2 C8 5.8(5)
C9 C8 N2 C2 -72.2(4)
C9 C8 N2 C3 102.3(4)
N1 C1 S1 Ni1 180.0(3)
C2 C1 S1 Ni1 0.0(3)
N2 C2 S2 Ni1 -179.7(3)
C1 C2 S2 Ni1 -0.8(3)
