#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/86/2208693.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2208693
loop_
_publ_author_name
'Wang, Yan-Ling'
'Xu, Dong'
'Yu, Wen-Tao'
'Wang, Xin-Qiang'
'Zhang, Guang-Hui'
_publ_section_title
;Hexadecyltrimethylammonium
 bis(2-thioxo-1,3-dithiole-4,5-dithiolato-κ²S⁴,S⁵)nickelate(III)
;
_journal_coeditor_code           OM6279
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m757
_journal_page_last               m759
_journal_paper_doi               10.1107/S1600536806008415
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '(C19 H42 N) [Ni (C3 S5)2]'
_chemical_formula_moiety         'C19 H42 N +, C6 Ni S10 -'
_chemical_formula_sum            'C25 H42 N Ni S10'
_chemical_formula_weight         735.91
_chemical_name_systematic
;
Hexadecyltrimethylammonium
bis(2-thioxo-1,3-dithiole-4,5-dithiolato-κ²S⁴,S⁵)nickel(III)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL-97
_cell_angle_alpha                93.426(5)
_cell_angle_beta                 99.218(5)
_cell_angle_gamma                100.494(5)
_cell_formula_units_Z            2
_cell_length_a                   8.051(5)
_cell_length_b                   12.240(5)
_cell_length_c                   18.316(5)
_cell_measurement_reflns_used    2878
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.140
_cell_measurement_theta_min      2.613
_cell_volume                     1744.5(14)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXTL (Bruker, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0600
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8662
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.172
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             774
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.439
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0523
_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)+(0.0848P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1552
_reflns_number_gt                4270
_reflns_number_total             6012
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om6279.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2208693
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.6995(5) 0.8698(3) -0.0285(2) 0.0695(11) Uani d . 1
C C2 0.6603(5) 0.7060(3) 0.0544(2) 0.0558(9) Uani d . 1
C C3 0.7316(5) 0.6680(3) -0.0023(2) 0.0541(9) Uani d . 1
C C4 0.6737(5) 0.2796(3) 0.1862(2) 0.0595(10) Uani d . 1
C C5 0.7598(5) 0.2460(3) 0.1345(2) 0.0559(9) Uani d . 1
C C6 0.7329(5) 0.0860(3) 0.2215(2) 0.0603(10) Uani d . 1
C C7 0.3001(10) -0.7192(5) 0.6261(4) 0.158(3) Uani d . 1
H H7A 0.2550 -0.7585 0.6647 0.237 Uiso calc R 1
H H7B 0.4230 -0.7086 0.6355 0.237 Uiso calc R 1
H H7C 0.2560 -0.7618 0.5790 0.237 Uiso calc R 1
C C8 0.2500(11) -0.6132(5) 0.6247(4) 0.156(3) Uani d . 1
H H8A 0.2911 -0.5750 0.6740 0.187 Uiso calc R 1
H H8B 0.1257 -0.6277 0.6178 0.187 Uiso calc R 1
C C9 0.2982(8) -0.5351(4) 0.5733(3) 0.115(2) Uani d . 1
H H9A 0.2560 -0.5725 0.5239 0.138 Uiso calc R 1
H H9B 0.4225 -0.5206 0.5799 0.138 Uiso calc R 1
C C10 0.2469(9) -0.4276(5) 0.5737(3) 0.121(2) Uani d . 1
H H10A 0.2935 -0.3888 0.6224 0.145 Uiso calc R 1
H H10B 0.1230 -0.4419 0.5694 0.145 Uiso calc R 1
C C11 0.2900(8) -0.3498(4) 0.5194(3) 0.1100(18) Uani d . 1
H H11A 0.2448 -0.3886 0.4706 0.132 Uiso calc R 1
H H11B 0.4140 -0.3341 0.5242 0.132 Uiso calc R 1
C C12 0.2335(8) -0.2412(5) 0.5204(3) 0.1123(18) Uani d . 1
H H12A 0.1102 -0.2566 0.5183 0.135 Uiso calc R 1
H H12B 0.2840 -0.2005 0.5682 0.135 Uiso calc R 1
C C13 0.2702(8) -0.1664(4) 0.4634(3) 0.1087(18) Uani d . 1
H H13A 0.2207 -0.2076 0.4156 0.130 Uiso calc R 1
H H13B 0.3936 -0.1507 0.4658 0.130 Uiso calc R 1
C C14 0.2139(8) -0.0594(4) 0.4633(3) 0.1028(17) Uani d . 1
H H14A 0.2669 -0.0168 0.5102 0.123 Uiso calc R 1
H H14B 0.0911 -0.0746 0.4626 0.123 Uiso calc R 1
C C15 0.2469(8) 0.0126(4) 0.4040(3) 0.1027(17) Uani d . 1
H H15A 0.1975 -0.0309 0.3570 0.123 Uiso calc R 1
H H15B 0.3700 0.0300 0.4059 0.123 Uiso calc R 1
C C16 0.1849(7) 0.1190(4) 0.4024(3) 0.0920(15) Uani d . 1
H H16A 0.2343 0.1629 0.4493 0.110 Uiso calc R 1
H H16B 0.0617 0.1019 0.4003 0.110 Uiso calc R 1
C C17 0.2200(7) 0.1899(4) 0.3421(3) 0.0904(14) Uani d . 1
H H17A 0.3432 0.2073 0.3443 0.108 Uiso calc R 1
H H17B 0.1708 0.1461 0.2952 0.108 Uiso calc R 1
C C18 0.1569(6) 0.2962(4) 0.3409(3) 0.0890(14) Uani d . 1
H H18A 0.1993 0.3374 0.3892 0.107 Uiso calc R 1
H H18B 0.0328 0.2782 0.3353 0.107 Uiso calc R 1
C C19 0.2003(7) 0.3724(4) 0.2839(3) 0.0902(14) Uani d . 1
H H19A 0.3243 0.3916 0.2897 0.108 Uiso calc R 1
H H19B 0.1586 0.3315 0.2355 0.108 Uiso calc R 1
C C20 0.1347(6) 0.4762(4) 0.2838(3) 0.0901(14) Uani d . 1
H H20A 0.1659 0.5130 0.3338 0.108 Uiso calc R 1
H H20B 0.0104 0.4566 0.2729 0.108 Uiso calc R 1
C C21 0.1908(6) 0.5589(3) 0.2322(2) 0.0796(13) Uani d . 1
H H21A 0.3143 0.5833 0.2442 0.096 Uiso calc R 1
H H21B 0.1628 0.5235 0.1818 0.096 Uiso calc R 1
C C22 0.1082(6) 0.6579(4) 0.2362(3) 0.0832(13) Uani d . 1
H H22A -0.0140 0.6331 0.2188 0.100 Uiso calc R 1
H H22B 0.1234 0.6858 0.2880 0.100 Uiso calc R 1
C C23 0.0528(6) 0.8343(4) 0.1999(3) 0.0995(16) Uani d . 1
H H23A -0.0631 0.7988 0.1793 0.149 Uiso calc R 1
H H23B 0.0873 0.8972 0.1732 0.149 Uiso calc R 1
H H23C 0.0594 0.8591 0.2512 0.149 Uiso calc R 1
C C24 0.3470(5) 0.8104(3) 0.2265(2) 0.0795(12) Uani d . 1
H H24A 0.4247 0.7600 0.2234 0.119 Uiso calc R 1
H H24B 0.3515 0.8353 0.2776 0.119 Uiso calc R 1
H H24C 0.3796 0.8735 0.1995 0.119 Uiso calc R 1
C C25 0.1603(6) 0.7180(3) 0.1154(2) 0.0765(12) Uani d . 1
H H25A 0.2355 0.6665 0.1104 0.115 Uiso calc R 1
H H25B 0.1944 0.7824 0.0898 0.115 Uiso calc R 1
H H25C 0.0447 0.6826 0.0943 0.115 Uiso calc R 1
N N1 0.1701(4) 0.7523(3) 0.19390(16) 0.0581(8) Uani d . 1
Ni Ni1 0.70329(6) 0.47444(3) 0.09273(2) 0.04893(18) Uani d . 1
S S1 0.7014(2) 0.99012(10) -0.06389(9) 0.1119(5) Uani d . 1
S S2 0.62251(16) 0.84072(8) 0.05183(7) 0.0751(3) Uani d . 1
S S3 0.77555(16) 0.76192(9) -0.06764(6) 0.0725(3) Uani d . 1
S S4 0.61629(14) 0.62448(8) 0.12397(6) 0.0649(3) Uani d . 1
S S5 0.77857(14) 0.53725(7) -0.00692(5) 0.0586(3) Uani d . 1
S S6 0.61368(15) 0.40746(8) 0.18825(6) 0.0707(3) Uani d . 1
S S7 0.81108(15) 0.33095(8) 0.06742(5) 0.0674(3) Uani d . 1
S S8 0.63257(17) 0.18651(10) 0.25266(7) 0.0810(4) Uani d . 1
S S9 0.81643(15) 0.11729(8) 0.14245(6) 0.0708(3) Uani d . 1
S S10 0.74829(17) -0.02838(10) 0.26272(8) 0.0876(4) Uani d . 1
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'
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_publ_flag
S1 C1 S2 122.9(2) ?
S1 C1 S3 123.4(3) ?
S2 C1 S3 113.7(2) ?
C3 C2 S4 120.8(3) ?
C3 C2 S2 116.0(3) ?
S4 C2 S2 123.1(2) ?
C2 C3 S5 121.5(3) ?
C2 C3 S3 115.7(3) ?
S5 C3 S3 122.8(2) ?
C5 C4 S6 122.3(3) ?
C5 C4 S8 115.6(3) ?
S6 C4 S8 122.2(2) ?
C4 C5 S7 120.0(3) ?
C4 C5 S9 116.2(3) ?
S7 C5 S9 123.8(2) ?
S10 C6 S8 123.4(2) ?
S10 C6 S9 123.7(2) ?
S8 C6 S9 112.9(2) ?
C8 C7 H7A 109.5 ?
C8 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C8 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C7 C8 C9 122.7(7) ?
C7 C8 H8A 106.6 ?
C9 C8 H8A 106.6 ?
C7 C8 H8B 106.6 ?
C9 C8 H8B 106.6 ?
H8A C8 H8B 106.6 ?
C8 C9 C10 121.5(6) ?
C8 C9 H9A 106.9 ?
C10 C9 H9A 106.9 ?
C8 C9 H9B 106.9 ?
C10 C9 H9B 106.9 ?
H9A C9 H9B 106.7 ?
C9 C10 C11 121.6(5) ?
C9 C10 H10A 106.9 ?
C11 C10 H10A 106.9 ?
C9 C10 H10B 106.9 ?
C11 C10 H10B 106.9 ?
H10A C10 H10B 106.7 ?
C10 C11 C12 120.4(5) ?
C10 C11 H11A 107.2 ?
C12 C11 H11A 107.2 ?
C10 C11 H11B 107.2 ?
C12 C11 H11B 107.2 ?
H11A C11 H11B 106.9 ?
C13 C12 C11 119.8(5) ?
C13 C12 H12A 107.4 ?
C11 C12 H12A 107.4 ?
C13 C12 H12B 107.4 ?
C11 C12 H12B 107.4 ?
H12A C12 H12B 106.9 ?
C12 C13 C14 120.3(5) ?
C12 C13 H13A 107.2 ?
C14 C13 H13A 107.2 ?
C12 C13 H13B 107.2 ?
C14 C13 H13B 107.2 ?
H13A C13 H13B 106.9 ?
C13 C14 C15 119.4(5) ?
C13 C14 H14A 107.5 ?
C15 C14 H14A 107.5 ?
C13 C14 H14B 107.5 ?
C15 C14 H14B 107.5 ?
H14A C14 H14B 107.0 ?
C14 C15 C16 119.5(5) ?
C14 C15 H15A 107.5 ?
C16 C15 H15A 107.5 ?
C14 C15 H15B 107.5 ?
C16 C15 H15B 107.5 ?
H15A C15 H15B 107.0 ?
C15 C16 C17 118.3(4) ?
C15 C16 H16A 107.7 ?
C17 C16 H16A 107.7 ?
C15 C16 H16B 107.7 ?
C17 C16 H16B 107.7 ?
H16A C16 H16B 107.1 ?
C18 C17 C16 117.9(4) ?
C18 C17 H17A 107.8 ?
C16 C17 H17A 107.8 ?
C18 C17 H17B 107.8 ?
C16 C17 H17B 107.8 ?
H17A C17 H17B 107.2 ?
C17 C18 C19 118.9(4) ?
C17 C18 H18A 107.6 ?
C19 C18 H18A 107.6 ?
C17 C18 H18B 107.6 ?
C19 C18 H18B 107.6 ?
H18A C18 H18B 107.0 ?
C20 C19 C18 117.6(4) ?
C20 C19 H19A 107.9 ?
C18 C19 H19A 107.9 ?
C20 C19 H19B 107.9 ?
C18 C19 H19B 107.9 ?
H19A C19 H19B 107.2 ?
C19 C20 C21 118.5(4) ?
C19 C20 H20A 107.7 ?
C21 C20 H20A 107.7 ?
C19 C20 H20B 107.7 ?
C21 C20 H20B 107.7 ?
H20A C20 H20B 107.1 ?
C22 C21 C20 112.3(4) ?
C22 C21 H21A 109.2 ?
C20 C21 H21A 109.2 ?
C22 C21 H21B 109.2 ?
C20 C21 H21B 109.2 ?
H21A C21 H21B 107.9 ?
N1 C22 C21 117.0(4) ?
N1 C22 H22A 108.0 ?
C21 C22 H22A 108.0 ?
N1 C22 H22B 108.0 ?
C21 C22 H22B 108.0 ?
H22A C22 H22B 107.3 ?
N1 C23 H23A 109.5 ?
N1 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
N1 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
N1 C24 H24A 109.5 ?
N1 C24 H24B 109.5 ?
H24A C24 H24B 109.5 ?
N1 C24 H24C 109.5 ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
N1 C25 H25A 109.5 ?
N1 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
N1 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
C25 N1 C24 109.9(3) ?
C25 N1 C22 112.5(3) ?
C24 N1 C22 112.0(3) ?
C25 N1 C23 108.3(3) ?
C24 N1 C23 107.7(3) ?
C22 N1 C23 106.2(3) ?
S6 Ni1 S7 92.90(4) y
S6 Ni1 S5 176.61(5) y
S7 Ni1 S5 87.25(4) y
S6 Ni1 S4 87.08(4) y
S7 Ni1 S4 175.07(5) y
S5 Ni1 S4 93.06(4) y
C1 S2 C2 97.37(19) ?
C1 S3 C3 97.20(19) ?
C2 S4 Ni1 102.45(13) ?
C3 S5 Ni1 102.12(14) ?
C4 S6 Ni1 101.82(13) ?
C5 S7 Ni1 103.01(13) ?
C6 S8 C4 97.62(19) ?
C6 S9 C5 97.63(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 S1 1.642(4) y
C1 S2 1.719(4) y
C1 S3 1.719(4) y
C2 C3 1.362(5) y
C2 S4 1.706(4) y
C2 S2 1.733(3) y
C3 S5 1.710(3) y
C3 S3 1.742(3) y
C4 C5 1.347(5) y
C4 S6 1.720(4) y
C4 S8 1.746(3) y
C5 S7 1.709(4) y
C5 S9 1.726(3) y
C6 S10 1.645(4) y
C6 S8 1.708(4) y
C6 S9 1.726(4) y
C7 C8 1.428(7) ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
C8 C9 1.429(7) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 C10 1.449(7) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C11 1.455(7) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 C12 1.481(7) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 C13 1.461(6) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 C14 1.461(6) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 C15 1.466(6) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 C16 1.477(6) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 C17 1.477(6) ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C17 C18 1.481(6) ?
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C18 C19 1.481(6) ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 C20 1.461(6) ?
C19 H19A 0.9700 ?
C19 H19B 0.9700 ?
C20 C21 1.487(5) ?
C20 H20A 0.9700 ?
C20 H20B 0.9700 ?
C21 C22 1.487(6) ?
C21 H21A 0.9700 ?
C21 H21B 0.9700 ?
C22 N1 1.485(5) ?
C22 H22A 0.9700 ?
C22 H22B 0.9700 ?
C23 N1 1.509(5) ?
C23 H23A 0.9600 ?
C23 H23B 0.9600 ?
C23 H23C 0.9600 ?
C24 N1 1.483(5) ?
C24 H24A 0.9600 ?
C24 H24B 0.9600 ?
C24 H24C 0.9600 ?
C25 N1 1.460(4) ?
C25 H25A 0.9600 ?
C25 H25B 0.9600 ?
C25 H25C 0.9600 ?
Ni1 S6 2.1479(11) y
Ni1 S7 2.1540(12) y
Ni1 S5 2.1545(11) y
Ni1 S4 2.1592(12) y
