#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/20/2202098.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_2202098
loop_
_publ_author_name
'Tong, Wen-Jun'
'Liu, Ling'
'Meng, Qing-Jin'
'Li, Yi-Zhi'
'Yao, Yuan-Gen'
_publ_section_title
;
 1-Methyl-N-(4-nitrobenzyl)pyridinium
 bis(2-thioxo-1,3-dithiole-4,5-dithiolato)nickelate(III)
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m3
_journal_page_last               m5
_journal_paper_doi               10.1107/S1600536802022006
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '(C13 H13 N2 O2) [Ni (C3 S5)2]'
_chemical_formula_moiety         'C13 H13 N2 O2 +, C6 Ni S10 -'
_chemical_formula_sum            'C19 H13 N2 Ni O2 S10'
_chemical_formula_weight         680.70
_chemical_name_systematic        ?
_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
_cell_angle_alpha                105.430(10)
_cell_angle_beta                 92.450(10)
_cell_angle_gamma                108.340(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9820(10)
_cell_length_b                   12.364(2)
_cell_length_c                   13.978(2)
_cell_measurement_reflns_used    885
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.39
_cell_measurement_theta_min      2.19
_cell_volume                     1250.1(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0877
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6270
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    1.635
_exptl_absorpt_correction_T_max  0.714
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             690
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.324
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.60(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0558
_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)+(0.02P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2588
_reflns_number_total             4322
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6200.cif
_cod_data_source_block           I
_cod_database_code               2202098
_cod_database_fobs_code          2202098
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Ni1 0.52897(9) 0.25431(6) 0.33683(5) 0.0427(2) Uani d . 1 . . Ni
C1 0.3490(7) 0.0211(5) 0.3805(4) 0.0436(14) Uani d . 1 . . C
C2 0.1901(7) -0.0984(5) 0.4992(4) 0.0501(15) Uani d . 1 . . C
C3 0.3338(6) 0.1043(5) 0.4629(4) 0.0441(14) Uani d . 1 . . C
C4 0.7222(7) 0.4007(5) 0.2079(4) 0.0437(14) Uani d . 1 . . C
C5 0.8959(7) 0.6045(5) 0.1781(4) 0.0486(15) Uani d . 1 . . C
C6 0.7169(7) 0.4849(5) 0.2914(4) 0.0426(14) Uani d . 1 . . C
S1 0.4539(2) 0.06132(13) 0.28558(10) 0.0503(4) Uani d . 1 . . S
S2 0.2602(2) -0.12605(13) 0.38170(11) 0.0546(4) Uani d . 1 . . S
S3 0.0891(2) -0.20400(15) 0.54650(12) 0.0694(5) Uani d . 1 . . S
S4 0.2337(2) 0.05109(14) 0.55649(11) 0.0565(4) Uani d . 1 . . S
S5 0.4099(2) 0.25278(13) 0.47240(11) 0.0536(4) Uani d . 1 . . S
S6 0.62811(19) 0.25232(13) 0.19579(10) 0.0519(4) Uani d . 1 . . S
S7 0.83319(19) 0.45336(14) 0.11630(10) 0.0504(4) Uani d . 1 . . S
S8 1.0164(2) 0.70748(15) 0.13238(12) 0.0682(5) Uani d . 1 . . S
S9 0.8223(2) 0.63313(13) 0.29412(11) 0.0528(4) Uani d . 1 . . S
S10 0.6176(2) 0.44666(13) 0.39030(10) 0.0503(4) Uani d . 1 . . S
C7 0.9103(7) 0.6524(5) 0.7213(4) 0.0480(15) Uani d . 1 . . C
H7 0.9824 0.7263 0.7178 0.058 Uiso calc R 1 . . H
C8 0.8917(7) 0.5533(5) 0.6443(4) 0.0525(15) Uani d . 1 . . C
H8 0.9484 0.5594 0.5882 0.063 Uiso calc R 1 . . H
C9 0.7882(7) 0.4448(5) 0.6508(4) 0.0537(16) Uani d . 1 . . C
H9 0.7753 0.3757 0.5998 0.064 Uiso calc R 1 . . H
C10 0.7038(7) 0.4391(5) 0.7335(4) 0.0525(16) Uani d . 1 . . C
H10 0.6326 0.3653 0.7377 0.063 Uiso calc R 1 . . H
C11 0.7216(7) 0.5386(5) 0.8095(4) 0.0459(15) Uani d . 1 . . C
C12 0.8457(7) 0.7557(5) 0.8845(4) 0.0515(15) Uani d . 1 . . C
H12A 0.8660 0.7407 0.9479 0.062 Uiso calc R 1 . . H
H12B 0.7336 0.7708 0.8821 0.062 Uiso calc R 1 . . H
C13 0.9930(7) 0.8669(5) 0.8824(4) 0.0460(14) Uani d . 1 . . C
C14 0.9762(7) 0.9268(5) 0.8149(4) 0.0521(16) Uani d . 1 . . C
H14 0.8722 0.8987 0.7698 0.062 Uiso calc R 1 . . H
C15 1.1106(8) 1.0277(5) 0.8129(4) 0.0540(16) Uani d . 1 . . C
H15 1.1003 1.0670 0.7659 0.065 Uiso calc R 1 . . H
C16 1.2592(8) 1.0685(5) 0.8816(4) 0.0525(16) Uani d . 1 . . C
C17 1.2808(7) 1.0157(5) 0.9533(4) 0.0517(16) Uani d . 1 . . C
H17 1.3821 1.0473 1.0008 0.062 Uiso calc R 1 . . H
C18 1.1437(7) 0.9119(5) 0.9516(4) 0.0479(15) Uani d . 1 . . C
H18 1.1545 0.8722 0.9982 0.058 Uiso calc R 1 . . H
C19 0.6364(7) 0.5339(5) 0.9013(4) 0.0580(16) Uani d . 1 . . C
H19A 0.7268 0.5649 0.9586 0.087 Uiso calc R 1 . . H
H19B 0.5677 0.4527 0.8957 0.087 Uiso calc R 1 . . H
H19C 0.5596 0.5809 0.9090 0.087 Uiso calc R 1 . . H
N1 0.8275(5) 0.6464(4) 0.8022(3) 0.0434(11) Uani d . 1 . . N
N2 1.4052(9) 1.1774(6) 0.8802(5) 0.087 Uani d . 1 . . N
O1 1.3955(6) 1.2170(4) 0.8104(4) 0.1025(17) Uani d . 1 . . O
O2 1.5303(7) 1.2182(5) 0.9458(4) 0.135(2) Uani d . 1 . . O
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'
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
S6 Ni1 S5 175.72(7) y
S6 Ni1 S10 93.35(6) y
S5 Ni1 S10 87.64(6) y
S6 Ni1 S1 86.27(6) y
S5 Ni1 S1 92.95(6) y
S10 Ni1 S1 176.97(7) y
C3 C1 S1 121.4(4) ?
C3 C1 S2 115.5(4) ?
S1 C1 S2 123.2(3) y
S3 C2 S4 124.5(3) y
S3 C2 S2 122.8(3) y
S4 C2 S2 112.7(3) y
C1 C3 S5 121.4(4) ?
C1 C3 S4 116.4(4) ?
S5 C3 S4 122.2(3) y
C6 C4 S6 121.3(4) y
C6 C4 S7 116.0(4) y
S6 C4 S7 122.8(3) y
S8 C5 S7 123.1(3) y
S8 C5 S9 124.2(3) y
S7 C5 S9 112.6(3) y
C4 C6 S10 121.4(4) ?
C4 C6 S9 116.1(4) ?
S10 C6 S9 122.5(3) y
C1 S1 Ni1 102.06(19) ?
C1 S2 C2 97.6(3) ?
C2 S4 C3 97.8(3) ?
C3 S5 Ni1 102.15(19) ?
C4 S6 Ni1 102.34(19) ?
C5 S7 C4 97.9(3) ?
C5 S9 C6 97.4(3) ?
C6 S10 Ni1 101.65(19) ?
N1 C7 C8 121.8(5) ?
N1 C7 H7 119.1 ?
C8 C7 H7 119.1 ?
C7 C8 C9 118.8(6) ?
C7 C8 H8 120.6 ?
C9 C8 H8 120.6 ?
C8 C9 C10 119.2(6) ?
C8 C9 H9 120.4 ?
C10 C9 H9 120.4 ?
C11 C10 C9 121.6(6) ?
C11 C10 H10 119.2 ?
C9 C10 H10 119.2 ?
C10 C11 N1 118.4(5) ?
C10 C11 C19 122.4(5) ?
N1 C11 C19 119.1(5) ?
N1 C12 C13 115.5(4) ?
N1 C12 H12A 108.4 ?
C13 C12 H12A 108.4 ?
N1 C12 H12B 108.4 ?
C13 C12 H12B 108.4 ?
H12A C12 H12B 107.5 ?
C14 C13 C18 119.1(5) ?
C14 C13 C12 121.1(6) ?
C18 C13 C12 119.7(6) ?
C13 C14 C15 121.1(6) ?
C13 C14 H14 119.5 ?
C15 C14 H14 119.5 ?
C16 C15 C14 118.1(6) ?
C16 C15 H15 120.9 ?
C14 C15 H15 120.9 ?
C15 C16 C17 123.6(6) ?
C15 C16 N2 118.7(6) ?
C17 C16 N2 117.8(6) ?
C16 C17 C18 116.7(6) ?
C16 C17 H17 121.6 ?
C18 C17 H17 121.6 ?
C13 C18 C17 121.3(6) ?
C13 C18 H18 119.3 ?
C17 C18 H18 119.3 ?
C11 C19 H19A 109.5 ?
C11 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C11 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C7 N1 C11 120.2(5) ?
C7 N1 C12 121.1(5) ?
C11 N1 C12 118.7(5) ?
O2 N2 O1 123.7(7) ?
O2 N2 C16 118.3(7) ?
O1 N2 C16 117.9(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 S6 . 2.1526(16) y
Ni1 S5 . 2.1577(16) y
Ni1 S10 . 2.1599(16) y
Ni1 S1 . 2.1725(16) y
C1 C3 . 1.363(6) ?
C1 S1 . 1.701(5) y
C1 S2 . 1.737(5) y
C2 S3 . 1.623(6) y
C2 S4 . 1.721(6) y
C2 S2 . 1.740(5) y
C3 S5 . 1.709(5) y
C3 S4 . 1.732(5) y
C4 C6 . 1.354(6) ?
C4 S6 . 1.708(6) y
C4 S7 . 1.739(5) y
C5 S8 . 1.634(6) y
C5 S7 . 1.733(6) y
C5 S9 . 1.735(5) y
C6 S10 . 1.722(5) y
C6 S9 . 1.749(5) y
C7 N1 . 1.341(6) ?
C7 C8 . 1.361(6) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.366(7) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.369(7) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.358(7) ?
C10 H10 . 0.9300 ?
C11 N1 . 1.368(6) ?
C11 C19 . 1.484(7) ?
C12 N1 . 1.485(6) ?
C12 C13 . 1.510(7) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.370(8) ?
C13 C18 . 1.373(7) ?
C14 C15 . 1.374(7) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.361(7) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.366(8) ?
C16 N2 . 1.483(8) ?
C17 C18 . 1.394(7) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
N2 O2 . 1.204(7) ?
N2 O1 . 1.213(7) ?
