#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/63/2216368.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_2216368
loop_
_publ_author_name
'Ai-Qun Zhou'
'Chun-Lin Ni'
_publ_section_title
;
 Bis[1-(4-fluorobenzyl)pyridinium]
 bis(2,2-dicyanoethene-1,1-dithiolato-κ²S,S')nickelate(II)
;
_journal_coeditor_code           CI2509
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m3084
_journal_page_last               m3084
_journal_paper_doi               10.1107/S160053680705814X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '(C12 H11 F N)2 [Ni (C4 N2 S2)2]'
_chemical_formula_moiety         '2(C12 H11 F N), C8 N4 Ni S4'
_chemical_formula_sum            'C32 H22 F2 N6 Ni S4'
_chemical_formula_weight         715.51
_chemical_name_systematic
;
Bis[1-(4-fluorobenzyl)pyridinium]
bis(2,2-dicyanoethene-1,1-dithiolato-κ²S,S')nickelate(II)
;
_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           SHELXL2000
_cell_angle_alpha                71.680(10)
_cell_angle_beta                 74.930(10)
_cell_angle_gamma                82.110(10)
_cell_formula_units_Z            1
_cell_length_a                   7.0850(10)
_cell_length_b                   9.0480(10)
_cell_length_c                   13.1820(10)
_cell_measurement_reflns_used    3505
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      29.46
_cell_measurement_theta_min      2.38
_cell_volume                     773.19(16)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0089
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4185
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.1686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0707
_reflns_number_gt                2568
_reflns_number_total             2695
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2509.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_original_cell_volume        773.19(15)
_cod_database_code               2216368
_cod_database_fobs_code          2216368
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
Ni Ni1 1.0000 0.0000 0.5000 0.03971(11) Uani d S 1
S S1 0.87140(6) -0.02721(5) 0.67579(3) 0.04361(12) Uani d . 1
S S2 0.86668(7) 0.23756(5) 0.49460(3) 0.04755(13) Uani d . 1
N N1 0.7048(3) 0.1351(2) 0.91290(14) 0.0747(5) Uani d . 1
N N2 0.6279(3) 0.54849(19) 0.63808(14) 0.0611(4) Uani d . 1
N N3 0.33540(19) 0.96970(15) 0.76440(11) 0.0391(3) Uani d . 1
F F1 -0.34351(17) 0.52632(13) 0.90040(10) 0.0665(3) Uani d . 1
C C1 0.8128(2) 0.17017(19) 0.63538(12) 0.0376(3) Uani d . 1
C C2 0.7406(2) 0.25975(19) 0.70595(13) 0.0398(3) Uani d . 1
C C3 0.7188(3) 0.1919(2) 0.82093(14) 0.0479(4) Uani d . 1
C C4 0.6808(2) 0.4202(2) 0.66752(13) 0.0440(4) Uani d . 1
C C5 0.1503(3) 0.64193(18) 0.78041(13) 0.0442(4) Uani d . 1
H H5 0.2537 0.6311 0.7225 0.053 Uiso calc R 1
C C6 -0.0245(3) 0.57681(19) 0.79671(14) 0.0472(4) Uani d . 1
H H6 -0.0406 0.5234 0.7500 0.057 Uiso calc R 1
C C7 -0.1730(3) 0.59274(19) 0.88309(14) 0.0474(4) Uani d . 1
C C8 -0.1575(3) 0.6725(2) 0.95277(14) 0.0516(4) Uani d . 1
H H8 -0.2619 0.6824 1.0104 0.062 Uiso calc R 1
C C9 0.0174(3) 0.7379(2) 0.93532(13) 0.0486(4) Uani d . 1
H H9 0.0310 0.7926 0.9818 0.058 Uiso calc R 1
C C10 0.1731(2) 0.72308(17) 0.84929(12) 0.0398(3) Uani d . 1
C C11 0.3599(3) 0.8020(2) 0.82662(15) 0.0469(4) Uani d . 1
H H11A 0.3924 0.7936 0.8954 0.056 Uiso calc R 1
H H11B 0.4663 0.7510 0.7843 0.056 Uiso calc R 1
C C12 0.2810(3) 1.0763(2) 0.81891(15) 0.0493(4) Uani d . 1
H H12 0.2663 1.0465 0.8947 0.059 Uiso calc R 1
C C13 0.2468(3) 1.2291(2) 0.76345(17) 0.0586(5) Uani d . 1
H H13 0.2076 1.3029 0.8017 0.070 Uiso calc R 1
C C14 0.2701(3) 1.2737(2) 0.65203(17) 0.0556(5) Uani d . 1
H H14 0.2482 1.3777 0.6140 0.067 Uiso calc R 1
C C15 0.3260(3) 1.1639(2) 0.59723(15) 0.0551(5) Uani d . 1
H H15 0.3426 1.1920 0.5214 0.066 Uiso calc R 1
C C16 0.3573(3) 1.0107(2) 0.65574(14) 0.0510(4) Uani d . 1
H H16 0.3941 0.9349 0.6191 0.061 Uiso calc R 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'
F F 0.0171 0.0103 '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'
Ni Ni 0.3393 1.1124 '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'
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_756 . 180
S1 Ni1 S2 2_756 . 101.201(18)
S1 Ni1 S2 . . 78.799(19)
S1 Ni1 S2 2_756 2_756 78.799(18)
S1 Ni1 S2 . 2_756 101.201(18)
S2 Ni1 S2 . 2_756 180
C1 S1 Ni1 . . 85.66(5)
C1 S2 Ni1 . . 85.51(6)
C16 N3 C12 . . 120.66(15)
C16 N3 C11 . . 119.73(15)
C12 N3 C11 . . 119.50(14)
C2 C1 S2 . . 125.81(13)
C2 C1 S1 . . 124.73(12)
S2 C1 S1 . . 109.42(9)
C1 C2 C3 . . 120.24(15)
C1 C2 C4 . . 121.83(14)
C3 C2 C4 . . 117.91(15)
N1 C3 C2 . . 178.5(2)
N2 C4 C2 . . 178.26(19)
C6 C5 C10 . . 120.72(16)
C6 C5 H5 . . 119.6
C10 C5 H5 . . 119.6
C7 C6 C5 . . 118.37(16)
C7 C6 H6 . . 120.8
C5 C6 H6 . . 120.8
F1 C7 C6 . . 118.43(17)
F1 C7 C8 . . 118.65(16)
C6 C7 C8 . . 122.93(17)
C7 C8 C9 . . 118.20(16)
C7 C8 H8 . . 120.9
C9 C8 H8 . . 120.9
C8 C9 C10 . . 120.87(16)
C8 C9 H9 . . 119.6
C10 C9 H9 . . 119.6
C5 C10 C9 . . 118.90(16)
C5 C10 C11 . . 120.24(15)
C9 C10 C11 . . 120.76(15)
N3 C11 C10 . . 109.83(13)
N3 C11 H11A . . 109.7
C10 C11 H11A . . 109.7
N3 C11 H11B . . 109.7
C10 C11 H11B . . 109.7
H11A C11 H11B . . 108.2
N3 C12 C13 . . 120.07(17)
N3 C12 H12 . . 120.0
C13 C12 H12 . . 120.0
C14 C13 C12 . . 120.18(19)
C14 C13 H13 . . 119.9
C12 C13 H13 . . 119.9
C15 C14 C13 . . 119.22(17)
C15 C14 H14 . . 120.4
C13 C14 H14 . . 120.4
C14 C15 C16 . . 119.12(17)
C14 C15 H15 . . 120.4
C16 C15 H15 . . 120.4
N3 C16 C15 . . 120.75(18)
N3 C16 H16 . . 119.6
C15 C16 H16 . . 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ni1 S1 2_756 2.2058(5)
Ni1 S1 . 2.2058(4)
Ni1 S2 . 2.2133(5)
Ni1 S2 2_756 2.2133(5)
S1 C1 . 1.7201(17)
S2 C1 . 1.7163(15)
N1 C3 . 1.142(2)
N2 C4 . 1.145(2)
N3 C16 . 1.334(2)
N3 C12 . 1.336(2)
N3 C11 . 1.491(2)
F1 C7 . 1.357(2)
C1 C2 . 1.377(2)
C2 C3 . 1.420(2)
C2 C4 . 1.423(2)
C5 C6 . 1.382(2)
C5 C10 . 1.385(2)
C5 H5 . 0.93
C6 C7 . 1.365(3)
C6 H6 . 0.93
C7 C8 . 1.366(3)
C8 C9 . 1.380(3)
C8 H8 . 0.93
C9 C10 . 1.387(2)
C9 H9 . 0.93
C10 C11 . 1.507(2)
C11 H11A . 0.97
C11 H11B . 0.97
C12 C13 . 1.368(3)
C12 H12 . 0.93
C13 C14 . 1.366(3)
C13 H13 . 0.93
C14 C15 . 1.364(3)
C14 H14 . 0.93
C15 C16 . 1.378(3)
C15 H15 . 0.93
C16 H16 . 0.93
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
_geom_hbond_publ_flag
C12 H12 N1 2_667 0.93 2.59 3.471(3) 157 y
C15 H15 N2 2_676 0.93 2.60 3.337(3) 136 y
