##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-04-01
_journal_date_accepted     2006-04-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      5
_journal_page_first     m1004
_journal_page_last     m1005
_journal_paper_category     EM
_journal_coeditor_code     SJ2035
_publ_contact_author_name     'Ruojie Tao'
_publ_contact_author_address
; Institute of Molecule and Crystal Engineering,
 School of Chemistry and Chemical Engineering,
 Henan University, Kaifeng, 475001, People's Republic of China
;
_publ_contact_author_email     rjtao@henu.edu.cn
_publ_contact_author_fax     '41 1 635 6812'
_publ_contact_author_phone     '41 1 635 4228'
_publ_section_title
;
N-(4-Bromobenzyl)-4-cyanopyridinium
bis(2-thioxo-1,3-dithiole-4,5-dithiolato)nickelate(III) acetone solvate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Shuang-Quan Zang' .
;
Institute of Molecular and Crystal Engineering
School of Chemistry and Chemical Engineering
Henan University
Kaifeng 475001
People's Republic of China
;
    'Yang Su' .
;
Coordination Chemistry Institute
State Key Laboratory of Coordination Chemistry
School of Chemistry and Chemical Engineering
Nanjing University
Nanjing 210093
People's Republic of China
;
    'Ruo-Jie Tao' .
;
Institute of Molecular and Crystal Engineering
School of Chemistry and Chemical Engineering
Henan University
Kaifeng 475001
People's Republic of China
;
data_I
_chemical_name_systematic
;
N-(4-Bromobenzyl)-4-cyanopyridinium
bis(2-thioxo-1,3-dithiole-4,5-dithiolato)nickelate(III) acetone solvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 Br N2 +, C6 Ni S10 -, C3 H6 O'
_chemical_formula_sum     'C22 H16 Br N2 Ni O S10'
_chemical_formula_iupac     '(C13 H10 Br N2) [Ni (C3 S5)2], C3 H6 O'
_chemical_formula_weight     783.66
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.197(2)
_cell_length_b     10.601(3)
_cell_length_c     15.714(4)
_cell_angle_alpha     98.265(5)
_cell_angle_beta     92.767(4)
_cell_angle_gamma     95.821(5)
_cell_volume     1505.3(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     804
_cell_measurement_theta_min     2.52
_cell_measurement_theta_max     22.42
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     black
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.1
_exptl_crystal_size_min     0.1
_exptl_crystal_density_diffrn     1.729
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     786.0
_exptl_absorpt_coefficient_mu     2.687
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.739
_exptl_absorpt_correction_T_max     0.760
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7546
_diffrn_reflns_av_R_equivalents     0.0634
_diffrn_reflns_av_sigmaI/netI     0.0907
_diffrn_reflns_theta_min     1.95
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     0.982
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 Two DFIX restraints on two bonds (C16--C19 and C21--C22).
 Twelve DELU restraints on the pyridine ring (N1 C14 > C18).
;
_reflns_number_total     5213
_reflns_number_gt     2680
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1034
_refine_ls_R_factor_gt     0.0551
_refine_ls_wR_factor_gt     0.0988
_refine_ls_wR_factor_ref     0.1051
_refine_ls_goodness_of_fit_ref     0.987
_refine_ls_restrained_S_all     0.987
_refine_ls_number_reflns     5213
_refine_ls_number_parameters     330
_refine_ls_number_restraints     14
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w = 1/[σ²(Fo²)+(0.02P)²+0.04P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.547
_refine_diff_density_min     -0.487
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
_computing_data_collection     'SMART  (Bruker, 2000)'
_computing_cell_refinement     'SAINT  (Bruker, 2000)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXTL (Bruker, 2000)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL and PLATON (Spek, 2003)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Ni Ni1 0.69767(8) 1.01287(6) 0.39871(4) 0.0618(2) Uani d . 1 . .
    C C1 0.8245(7) 1.3721(5) 0.1881(3) 0.0785(18) Uani d . 1 . .
    C C2 0.7028(6) 1.1851(5) 0.2615(3) 0.0658(16) Uani d . 1 . .
    C C3 0.8296(7) 1.2275(5) 0.3080(3) 0.0657(16) Uani d . 1 . .
    C C4 0.5717(6) 0.7980(5) 0.4908(3) 0.0594(15) Uani d . 1 . .
    C C5 0.6955(5) 0.8467(5) 0.5394(3) 0.0556(14) Uani d . 1 . .
    C C6 0.5817(6) 0.6592(5) 0.6133(3) 0.0716(17) Uani d . 1 . .
    C C7 0.1092(7) 0.0243(6) 0.8882(4) 0.0754(18) Uani d . 1 . .
    H H7 0.1206 -0.0475 0.8486 0.091 Uiso calc R 1 . .
    C C8 0.1850(7) 0.0406(6) 0.9673(4) 0.088(2) Uani d . 1 . .
    H H8 0.2463 -0.0192 0.9809 0.105 Uiso calc R 1 . .
    C C9 0.1687(8) 0.1457(8) 1.0250(4) 0.096 Uani d . 1 . .
    C C10 0.0809(7) 0.2305(6) 1.0055(4) 0.086(2) Uani d . 1 . .
    H H10 0.0711 0.3025 1.0454 0.104 Uiso calc R 1 . .
    C C11 0.0035(7) 0.2123(5) 0.9258(4) 0.0740(17) Uani d . 1 . .
    H H11 -0.0594 0.2713 0.9132 0.089 Uiso calc R 1 . .
    C C12 0.0188(6) 0.1087(5) 0.8659(3) 0.0607(15) Uani d . 1 . .
    C C13 -0.0633(7) 0.0870(5) 0.7803(3) 0.0744(18) Uani d . 1 . .
    H H13A -0.0514 0.0017 0.7514 0.089 Uiso calc R 1 . .
    H H13B -0.1667 0.0905 0.7886 0.089 Uiso calc R 1 . .
    C C14 -0.1106(7) 0.2299(5) 0.6763(3) 0.0714(17) Uani d U 1 . .
    H H14 -0.2100 0.2076 0.6808 0.086 Uiso calc R 1 . .
    C C15 -0.0674(7) 0.3116(5) 0.6198(3) 0.0700(16) Uani d U 1 . .
    H H15 -0.1369 0.3437 0.5863 0.084 Uiso calc R 1 . .
    C C16 0.0804(7) 0.3460(5) 0.6130(3) 0.0594(14) Uani d DU 1 . .
    C C17 0.1756(7) 0.2979(5) 0.6660(3) 0.0700(16) Uani d U 1 . .
    H H17 0.2756 0.3217 0.6651 0.084 Uiso calc R 1 . .
    C C18 0.1259(7) 0.2144(5) 0.7209(3) 0.0694(16) Uani d U 1 . .
    H H18 0.1927 0.1811 0.7556 0.083 Uiso calc R 1 . .
    C C19 0.1278(6) 0.4236(5) 0.5553(3) 0.0660(16) Uani d D 1 . .
    O O1 0.6721(7) 0.2594(6) 0.8238(4) 0.169(3) Uani d . 1 . .
    C C20 0.6395(11) 0.4577(10) 0.8934(5) 0.200(5) Uani d . 1 . .
    H H20A 0.7228 0.4857 0.8637 0.300 Uiso calc R 1 . .
    H H20B 0.6624 0.4763 0.9545 0.300 Uiso calc R 1 . .
    H H20C 0.5580 0.5018 0.8785 0.300 Uiso calc R 1 . .
    C C21 0.6025(10) 0.3226(9) 0.8689(5) 0.123(3) Uani d D 1 . .
    C C22 0.4850(11) 0.2644(11) 0.9124(7) 0.302(9) Uani d D 1 . .
    H H22A 0.3941 0.2626 0.8792 0.453 Uiso calc R 1 . .
    H H22B 0.4797 0.3133 0.9683 0.453 Uiso calc R 1 . .
    H H22C 0.5027 0.1784 0.9186 0.453 Uiso calc R 1 . .
    N N1 -0.0145(5) 0.1818(4) 0.7244(3) 0.0591(12) Uani d U 1 . .
    S S1 0.8584(2) 1.48341(17) 0.12731(12) 0.1117(7) Uani d . 1 . .
    S S2 0.6668(2) 1.26554(16) 0.17419(10) 0.0865(5) Uani d . 1 . .
    S S3 0.93637(19) 1.35129(14) 0.27390(10) 0.0794(5) Uani d . 1 . .
    S S4 0.58654(17) 1.05888(15) 0.28470(9) 0.0774(5) Uani d . 1 . .
    S S5 0.88065(16) 1.15543(13) 0.39461(9) 0.0686(4) Uani d . 1 . .
    S S6 0.52012(16) 0.86344(14) 0.40212(9) 0.0690(4) Uani d . 1 . .
    S S7 0.80795(16) 0.97166(14) 0.51400(9) 0.0680(4) Uani d . 1 . .
    S S8 0.47060(17) 0.66924(15) 0.52389(9) 0.0760(5) Uani d . 1 . .
    S S9 0.73328(17) 0.77180(15) 0.62845(9) 0.0714(5) Uani d . 1 . .
    S S10 0.5507(2) 0.55030(18) 0.67645(10) 0.1042(7) Uani d . 1 . .
    Br Br1 0.27186(10) 0.17125(9) 1.13312(5) 0.1400(4) Uani d . 1 . .
    N N2 0.1693(5) 0.4865(5) 0.5061(3) 0.0831(15) Uani d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 S7 . 2.1545(16) yes
    Ni1 S5 . 2.1547(16) yes
    Ni1 S4 . 2.1605(16) yes
    Ni1 S6 . 2.1649(16) yes
    C1 S1 . 1.638(6) ?
    C1 S3 . 1.709(6) ?
    C1 S2 . 1.730(6) ?
    C2 C3 . 1.347(7) ?
    C2 S4 . 1.719(6) ?
    C2 S2 . 1.751(5) ?
    C3 S5 . 1.722(6) ?
    C3 S3 . 1.722(6) ?
    C4 C5 . 1.353(6) ?
    C4 S6 . 1.711(5) ?
    C4 S8 . 1.730(5) ?
    C5 S7 . 1.702(5) ?
    C5 S9 . 1.742(5) ?
    C6 S10 . 1.640(6) ?
    C6 S8 . 1.719(5) ?
    C6 S9 . 1.724(5) ?
    C7 C12 . 1.352(7) ?
    C7 C8 . 1.374(7) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.358(8) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.325(8) ?
    C9 Br1 . 1.876(7) ?
    C10 C11 . 1.389(7) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.363(6) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.487(6) ?
    C13 N1 . 1.477(6) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 N1 . 1.323(6) ?
    C14 C15 . 1.371(7) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.384(7) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.365(7) ?
    C16 C19 . 1.367(7) ?
    C17 C18 . 1.384(7) ?
    C17 H17 . 0.9300 ?
    C18 N1 . 1.308(6) ?
    C18 H18 . 0.9300 ?
    C19 N2 . 1.146(6) ?
    O1 C21 . 1.165(8) ?
    C20 C21 . 1.430(10) ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
    C21 C22 . 1.440(14) ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    S7 Ni1 S5 . . 86.20(6) yes
    S7 Ni1 S4 . . 178.59(6) yes
    S5 Ni1 S4 . . 93.18(6) yes
    S7 Ni1 S6 . . 92.71(6) yes
    S5 Ni1 S6 . . 177.58(7) yes
    S4 Ni1 S6 . . 87.96(6) yes
    S1 C1 S3 . . 124.3(4) ?
    S1 C1 S2 . . 123.1(4) ?
    S3 C1 S2 . . 112.6(3) ?
    C3 C2 S4 . . 122.4(5) ?
    C3 C2 S2 . . 115.2(5) ?
    S4 C2 S2 . . 122.4(4) ?
    C2 C3 S5 . . 120.2(5) ?
    C2 C3 S3 . . 116.5(5) ?
    S5 C3 S3 . . 123.2(4) ?
    C5 C4 S6 . . 120.7(4) ?
    C5 C4 S8 . . 116.5(4) ?
    S6 C4 S8 . . 122.9(3) ?
    C4 C5 S7 . . 121.9(4) ?
    C4 C5 S9 . . 115.7(4) ?
    S7 C5 S9 . . 122.4(3) ?
    S10 C6 S8 . . 123.6(3) ?
    S10 C6 S9 . . 122.9(3) ?
    S8 C6 S9 . . 113.5(3) ?
    C12 C7 C8 . . 122.5(6) ?
    C12 C7 H7 . . 118.7 ?
    C8 C7 H7 . . 118.7 ?
    C9 C8 C7 . . 118.6(7) ?
    C9 C8 H8 . . 120.7 ?
    C7 C8 H8 . . 120.7 ?
    C10 C9 C8 . . 120.6(7) ?
    C10 C9 Br1 . . 119.8(7) ?
    C8 C9 Br1 . . 119.6(6) ?
    C9 C10 C11 . . 120.2(6) ?
    C9 C10 H10 . . 119.9 ?
    C11 C10 H10 . . 119.9 ?
    C12 C11 C10 . . 120.7(6) ?
    C12 C11 H11 . . 119.6 ?
    C10 C11 H11 . . 119.6 ?
    C7 C12 C11 . . 117.3(6) ?
    C7 C12 C13 . . 121.1(6) ?
    C11 C12 C13 . . 121.7(6) ?
    N1 C13 C12 . . 113.1(4) ?
    N1 C13 H13A . . 109.0 ?
    C12 C13 H13A . . 109.0 ?
    N1 C13 H13B . . 109.0 ?
    C12 C13 H13B . . 109.0 ?
    H13A C13 H13B . . 107.8 ?
    N1 C14 C15 . . 121.7(6) ?
    N1 C14 H14 . . 119.1 ?
    C15 C14 H14 . . 119.1 ?
    C16 C15 C14 . . 119.6(6) ?
    C16 C15 H15 . . 120.2 ?
    C14 C15 H15 . . 120.2 ?
    C17 C16 C15 . . 116.8(5) ?
    C17 C16 C19 . . 121.9(6) ?
    C15 C16 C19 . . 121.3(6) ?
    C16 C17 C18 . . 121.1(6) ?
    C16 C17 H17 . . 119.5 ?
    C18 C17 H17 . . 119.5 ?
    N1 C18 C17 . . 120.4(6) ?
    N1 C18 H18 . . 119.8 ?
    C17 C18 H18 . . 119.8 ?
    N2 C19 C16 . . 178.5(7) ?
    C21 C20 H20A . . 109.5 ?
    C21 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C21 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    O1 C21 C22 . . 120.5(10) ?
    O1 C21 C20 . . 122.8(9) ?
    C22 C21 C20 . . 116.2(9) ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C18 N1 C14 . . 120.3(5) ?
    C18 N1 C13 . . 118.9(5) ?
    C14 N1 C13 . . 120.7(5) ?
    C1 S2 C2 . . 97.4(3) ?
    C1 S3 C3 . . 98.3(3) ?
    C2 S4 Ni1 . . 101.6(2) ?
    C3 S5 Ni1 . . 102.5(2) ?
    C4 S6 Ni1 . . 102.33(18) ?
    C5 S7 Ni1 . . 102.37(18) ?
    C6 S8 C4 . . 97.3(3) ?
    C6 S9 C5 . . 97.1(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C15 H15 N2 2_566 0.93 2.50 3.290(8) 143
    C14 H14 O1 1_455 0.93 2.55 3.135(8) 121
    C13 H13B O1 1_455 0.97 2.46 3.230(9) 136
