#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/24/2232456.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_2232456
loop_
_publ_author_name
'Liu, Guang-Xiang'
_publ_section_title
;
 1-(4-Iodobenzyl)-3-methylpyridinium
 bis(benzene-1,2-dithiolato)nickelate(III)
;
_journal_coeditor_code           RZ2652
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1607
_journal_paper_doi               10.1107/S1600536811043522
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '(C13 H13 I N) [Ni (C6 H4 S2)2]'
_chemical_formula_moiety         'C13 H13 I N +, C12 H8 Ni S4 -'
_chemical_formula_sum            'C25 H21 I N Ni S4'
_chemical_formula_weight         649.28
_chemical_name_systematic
;
1-(4-Iodobenzyl)-3-methylpyridinium bis(benzene-1,2-dithiolato)nickelate(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           SHELXL-97
_cell_angle_alpha                98.425(2)
_cell_angle_beta                 98.466(2)
_cell_angle_gamma                96.216(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3222(14)
_cell_length_b                   12.267(2)
_cell_length_c                   14.628(3)
_cell_measurement_reflns_used    2848
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.97
_cell_measurement_theta_min      2.39
_cell_volume                     1274.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6282
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    2.315
_exptl_absorpt_correction_T_max  0.7686
_exptl_absorpt_correction_T_min  0.5844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             646
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.524
_refine_diff_density_min         -1.913
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0559
_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)+(0.1231P)²+0.2746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1776
_refine_ls_wR_factor_ref         0.1957
_reflns_number_gt                3397
_reflns_number_total             4392
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2652.cif
_cod_data_source_block           I
_cod_database_code               2232456
_cod_database_fobs_code          2232456
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
_atom_site_symmetry_multiplicity
Ni Ni1 0.5000 0.0000 0.5000 0.0571(3) Uani d S 1 2
Ni Ni2 0.5000 1.0000 1.0000 0.0538(3) Uani d S 1 2
S S1 0.5791(2) 0.17354(14) 0.49920(11) 0.0667(4) Uani d . 1 1
S S2 0.4882(2) 0.03099(14) 0.64783(11) 0.0659(4) Uani d . 1 1
S S3 0.6151(2) 0.85051(14) 0.95682(12) 0.0704(4) Uani d . 1 1
S S4 0.2296(2) 0.90892(14) 0.99225(11) 0.0669(4) Uani d . 1 1
C C1 0.6117(8) 0.2356(5) 0.6168(4) 0.0623(14) Uani d . 1 1
C C2 0.6779(10) 0.3477(6) 0.6447(5) 0.0760(17) Uani d . 1 1
H H2 0.7043 0.3913 0.6002 0.091 Uiso calc R 1 1
C C3 0.7044(12) 0.3944(7) 0.7370(6) 0.091(2) Uani d . 1 1
H H3 0.7500 0.4694 0.7552 0.109 Uiso calc R 1 1
C C4 0.6634(11) 0.3302(7) 0.8039(5) 0.083(2) Uani d . 1 1
H H4 0.6796 0.3628 0.8666 0.100 Uiso calc R 1 1
C C5 0.6006(9) 0.2212(7) 0.7784(5) 0.0750(18) Uani d . 1 1
H H5 0.5756 0.1785 0.8238 0.090 Uiso calc R 1 1
C C6 0.5725(7) 0.1716(5) 0.6842(4) 0.0591(13) Uani d . 1 1
C C7 0.4339(9) 0.7433(5) 0.9440(4) 0.0654(15) Uani d . 1 1
C C8 0.4558(12) 0.6329(6) 0.9180(5) 0.086(2) Uani d . 1 1
H H8 0.5728 0.6151 0.9089 0.103 Uiso calc R 1 1
C C9 0.3127(16) 0.5509(7) 0.9055(6) 0.103(3) Uani d . 1 1
H H9 0.3319 0.4773 0.8892 0.124 Uiso calc R 1 1
C C10 0.1387(16) 0.5755(7) 0.9169(6) 0.106(3) Uani d . 1 1
H H10 0.0400 0.5183 0.9065 0.127 Uiso calc R 1 1
C C11 0.1057(12) 0.6862(7) 0.9440(5) 0.089(2) Uani d . 1 1
H H11 -0.0124 0.7031 0.9520 0.107 Uiso calc R 1 1
C C12 0.2610(9) 0.7703(5) 0.9585(4) 0.0652(15) Uani d . 1 1
C C13 0.1673(11) 0.6604(5) 0.6633(4) 0.0706(17) Uani d . 1 1
C C14 0.2677(9) 0.7576(5) 0.7112(4) 0.0623(14) Uani d . 1 1
H H14 0.3971 0.7642 0.7222 0.075 Uiso calc R 1 1
C C15 0.1810(8) 0.8458(5) 0.7435(4) 0.0604(14) Uani d . 1 1
H H15 0.2511 0.9111 0.7768 0.072 Uiso calc R 1 1
C C16 -0.0127(8) 0.8368(5) 0.7261(4) 0.0623(15) Uani d . 1 1
C C17 -0.1164(10) 0.7408(7) 0.6757(6) 0.087(2) Uani d . 1 1
H H17 -0.2457 0.7352 0.6629 0.104 Uiso calc R 1 1
C C18 -0.0259(13) 0.6526(6) 0.6441(6) 0.096(2) Uani d . 1 1
H H18 -0.0951 0.5875 0.6098 0.115 Uiso calc R 1 1
C C19 -0.1106(9) 0.9293(5) 0.7648(5) 0.0745(17) Uani d . 1 1
H H19A -0.1118 0.9272 0.8308 0.089 Uiso calc R 1 1
H H19B -0.2389 0.9173 0.7331 0.089 Uiso calc R 1 1
C C20 0.0515(11) 1.1170(7) 0.8295(5) 0.083(2) Uani d . 1 1
H H20 0.0471 1.0998 0.8890 0.100 Uiso calc R 1 1
C C21 0.1330(13) 1.2164(7) 0.8205(6) 0.092(2) Uani d . 1 1
H H21 0.1867 1.2676 0.8735 0.110 Uiso calc R 1 1
C C22 0.1377(10) 1.2435(6) 0.7331(5) 0.0774(17) Uani d . 1 1
H H22 0.1904 1.3139 0.7269 0.093 Uiso calc R 1 1
C C23 0.0637(7) 1.1657(5) 0.6538(4) 0.0599(14) Uani d . 1 1
C C24 -0.0168(8) 1.0640(5) 0.6672(4) 0.0631(14) Uani d . 1 1
H H24 -0.0671 1.0098 0.6156 0.076 Uiso calc R 1 1
C C25 0.0744(10) 1.1905(6) 0.5574(5) 0.0751(17) Uani d . 1 1
H H25A -0.0129 1.1379 0.5124 0.113 Uiso calc R 1 1
H H25B 0.1981 1.1853 0.5443 0.113 Uiso calc R 1 1
H H25C 0.0450 1.2643 0.5538 0.113 Uiso calc R 1 1
I I1 0.31005(11) 0.52863(4) 0.61739(4) 0.1153(3) Uani d . 1 1
N N1 -0.0234(7) 1.0421(4) 0.7546(4) 0.0637(12) Uani d . 1 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'
I I -0.4742 1.8119 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
S1 Ni1 S1 2_656 . 180.0000(10)
S1 Ni1 S2 2_656 . 88.41(6)
S1 Ni1 S2 . . 91.59(6)
S1 Ni1 S2 2_656 2_656 91.59(6)
S1 Ni1 S2 . 2_656 88.41(6)
S2 Ni1 S2 . 2_656 180.0
S4 Ni2 S4 . 2_677 180.0
S4 Ni2 S3 . 2_677 88.21(6)
S4 Ni2 S3 2_677 2_677 91.79(6)
S4 Ni2 S3 . . 91.79(6)
S4 Ni2 S3 2_677 . 88.21(6)
S3 Ni2 S3 2_677 . 180.0000(10)
C1 S1 Ni1 . . 104.7(2)
C6 S2 Ni1 . . 105.1(2)
C7 S3 Ni2 . . 105.5(2)
C12 S4 Ni2 . . 104.1(2)
C2 C1 C6 . . 119.1(6)
C2 C1 S1 . . 121.3(5)
C6 C1 S1 . . 119.6(5)
C3 C2 C1 . . 120.4(7)
C3 C2 H2 . . 119.8
C1 C2 H2 . . 119.8
C2 C3 C4 . . 120.2(7)
C2 C3 H3 . . 119.9
C4 C3 H3 . . 119.9
C5 C4 C3 . . 120.3(7)
C5 C4 H4 . . 119.8
C3 C4 H4 . . 119.8
C4 C5 C6 . . 120.4(7)
C4 C5 H5 . . 119.8
C6 C5 H5 . . 119.8
C1 C6 C5 . . 119.5(6)
C1 C6 S2 . . 118.5(5)
C5 C6 S2 . . 122.0(5)
C12 C7 C8 . . 119.4(6)
C12 C7 S3 . . 118.1(5)
C8 C7 S3 . . 122.5(6)
C9 C8 C7 . . 121.8(8)
C9 C8 H8 . . 119.1
C7 C8 H8 . . 119.1
C8 C9 C10 . . 120.0(8)
C8 C9 H9 . . 120.0
C10 C9 H9 . . 120.0
C9 C10 C11 . . 121.4(8)
C9 C10 H10 . . 119.3
C11 C10 H10 . . 119.3
C10 C11 C12 . . 116.9(8)
C10 C11 H11 . . 121.5
C12 C11 H11 . . 121.5
C7 C12 C11 . . 120.4(7)
C7 C12 S4 . . 120.4(5)
C11 C12 S4 . . 119.2(6)
C14 C13 C18 . . 119.2(7)
C14 C13 I1 . . 118.9(5)
C18 C13 I1 . . 121.9(5)
C13 C14 C15 . . 121.2(6)
C13 C14 H14 . . 119.4
C15 C14 H14 . . 119.4
C14 C15 C16 . . 119.5(6)
C14 C15 H15 . . 120.2
C16 C15 H15 . . 120.2
C17 C16 C15 . . 120.3(7)
C17 C16 C19 . . 119.2(6)
C15 C16 C19 . . 120.5(6)
C16 C17 C18 . . 119.2(7)
C16 C17 H17 . . 120.4
C18 C17 H17 . . 120.4
C17 C18 C13 . . 120.6(7)
C17 C18 H18 . . 119.7
C13 C18 H18 . . 119.7
C16 C19 N1 . . 113.7(5)
C16 C19 H19A . . 108.8
N1 C19 H19A . . 108.8
C16 C19 H19B . . 108.8
N1 C19 H19B . . 108.8
H19A C19 H19B . . 107.7
N1 C20 C21 . . 120.9(6)
N1 C20 H20 . . 119.5
C21 C20 H20 . . 119.5
C20 C21 C22 . . 120.1(7)
C20 C21 H21 . . 120.0
C22 C21 H21 . . 120.0
C21 C22 C23 . . 120.0(7)
C21 C22 H22 . . 120.0
C23 C22 H22 . . 120.0
C24 C23 C22 . . 117.5(5)
C24 C23 C25 . . 121.1(6)
C22 C23 C25 . . 121.4(6)
N1 C24 C23 . . 120.5(6)
N1 C24 H24 . . 119.7
C23 C24 H24 . . 119.7
C23 C25 H25A . . 109.5
C23 C25 H25B . . 109.5
H25A C25 H25B . . 109.5
C23 C25 H25C . . 109.5
H25A C25 H25C . . 109.5
H25B C25 H25C . . 109.5
C20 N1 C24 . . 121.0(6)
C20 N1 C19 . . 120.9(5)
C24 N1 C19 . . 118.1(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ni1 S1 2_656 2.1470(16)
Ni1 S1 . 2.1470(16)
Ni1 S2 . 2.1562(16)
Ni1 S2 2_656 2.1562(16)
Ni2 S4 . 2.1447(15)
Ni2 S4 2_677 2.1447(15)
Ni2 S3 2_677 2.1504(17)
Ni2 S3 . 2.1504(17)
S1 C1 . 1.747(6)
S2 C6 . 1.745(6)
S3 C7 . 1.732(6)
S4 C12 . 1.749(7)
C1 C2 . 1.388(9)
C1 C6 . 1.390(8)
C2 C3 . 1.364(11)
C2 H2 . 0.9300
C3 C4 . 1.388(10)
C3 H3 . 0.9300
C4 C5 . 1.345(11)
C4 H4 . 0.9300
C5 C6 . 1.399(9)
C5 H5 . 0.9300
C7 C12 . 1.381(9)
C7 C8 . 1.385(9)
C8 C9 . 1.344(12)
C8 H8 . 0.9300
C9 C10 . 1.369(14)
C9 H9 . 0.9300
C10 C11 . 1.414(13)
C10 H10 . 0.9300
C11 C12 . 1.419(9)
C11 H11 . 0.9300
C13 C14 . 1.367(9)
C13 C18 . 1.391(11)
C13 I1 . 2.101(7)
C14 C15 . 1.372(9)
C14 H14 . 0.9300
C15 C16 . 1.393(8)
C15 H15 . 0.9300
C16 C17 . 1.376(10)
C16 C19 . 1.492(9)
C17 C18 . 1.387(12)
C17 H17 . 0.9300
C18 H18 . 0.9300
C19 N1 . 1.498(8)
C19 H19A . 0.9700
C19 H19B . 0.9700
C20 N1 . 1.328(9)
C20 C21 . 1.331(11)
C20 H20 . 0.9300
C21 C22 . 1.371(10)
C21 H21 . 0.9300
C22 C23 . 1.388(9)
C22 H22 . 0.9300
C23 C24 . 1.374(8)
C23 C25 . 1.497(8)
C24 N1 . 1.352(7)
C24 H24 . 0.9300
C25 H25A . 0.9600
C25 H25B . 0.9600
C25 H25C . 0.9600
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
C19 H19B S2 1_465 0.97 2.81 3.613(7) 141
C20 H20 S4 2_577 0.93 2.86 3.580(8) 135
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_site_symmetry_1
_geom_torsion
S2 Ni1 S1 C1 . 6.0(2)
S2 Ni1 S1 C1 2_656 -174.0(2)
S1 Ni1 S2 C6 2_656 173.59(19)
S1 Ni1 S2 C6 . -6.41(19)
S4 Ni2 S3 C7 . -1.8(2)
S4 Ni2 S3 C7 2_677 178.2(2)
S3 Ni2 S4 C12 2_677 -178.97(19)
S3 Ni2 S4 C12 . 1.03(19)
Ni1 S1 C1 C2 . 175.1(5)
Ni1 S1 C1 C6 . -4.3(5)
C6 C1 C2 C3 . 0.1(10)
S1 C1 C2 C3 . -179.3(6)
C1 C2 C3 C4 . -0.7(12)
C2 C3 C4 C5 . 1.2(12)
C3 C4 C5 C6 . -1.2(11)
C2 C1 C6 C5 . -0.1(8)
S1 C1 C6 C5 . 179.3(4)
C2 C1 C6 S2 . 179.7(5)
S1 C1 C6 S2 . -0.9(6)
C4 C5 C6 C1 . 0.6(9)
C4 C5 C6 S2 . -179.1(5)
Ni1 S2 C6 C1 . 5.6(5)
Ni1 S2 C6 C5 . -174.6(4)
Ni2 S3 C7 C12 . 2.5(5)
Ni2 S3 C7 C8 . -178.9(5)
C12 C7 C8 C9 . 0.6(10)
S3 C7 C8 C9 . -178.0(6)
C7 C8 C9 C10 . 1.2(12)
C8 C9 C10 C11 . -1.6(13)
C9 C10 C11 C12 . 0.3(11)
C8 C7 C12 C11 . -2.0(9)
S3 C7 C12 C11 . 176.6(5)
C8 C7 C12 S4 . 179.5(5)
S3 C7 C12 S4 . -1.8(7)
C10 C11 C12 C7 . 1.6(9)
C10 C11 C12 S4 . -179.9(5)
Ni2 S4 C12 C7 . 0.2(5)
Ni2 S4 C12 C11 . -178.3(4)
C18 C13 C14 C15 . 2.4(9)
I1 C13 C14 C15 . -179.3(4)
C13 C14 C15 C16 . -0.9(8)
C14 C15 C16 C17 . -1.0(8)
C14 C15 C16 C19 . 176.8(5)
C15 C16 C17 C18 . 1.3(10)
C19 C16 C17 C18 . -176.5(6)
C16 C17 C18 C13 . 0.2(11)
C14 C13 C18 C17 . -2.0(10)
I1 C13 C18 C17 . 179.7(5)
C17 C16 C19 N1 . -138.2(6)
C15 C16 C19 N1 . 44.0(8)
N1 C20 C21 C22 . 1.1(13)
C20 C21 C22 C23 . -2.4(12)
C21 C22 C23 C24 . 1.7(10)
C21 C22 C23 C25 . -177.1(7)
C22 C23 C24 N1 . 0.3(8)
C25 C23 C24 N1 . 179.1(5)
C21 C20 N1 C24 . 1.0(11)
C21 C20 N1 C19 . 178.4(7)
C23 C24 N1 C20 . -1.7(8)
C23 C24 N1 C19 . -179.2(5)
C16 C19 N1 C20 . -115.7(7)
C16 C19 N1 C24 . 61.8(7)
