#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/34/2213421.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_2213421
loop_
_publ_author_name
'Jia-Rong Zhou'
'Chun-Lin Ni'
'Lin-Liang Yu'
_publ_section_title
;
 Bis(benzyltriphenylphosphonium)
 bis(1,2-dicyanoethene-1,2-dithiolato)nickel(II)
;
_journal_coeditor_code           KJ2051
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1427
_journal_page_last               m1429
_journal_paper_doi               10.1107/S1600536807018715
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '(C25 H22 P)2 [Ni (C4 N2 S2)2]'
_chemical_formula_moiety         '2(C25 H22 P +), C8 N4 Ni S4 2-'
_chemical_formula_sum            'C58 H44 N4 Ni P2 S4'
_chemical_formula_weight         1045.86
_chemical_name_systematic
;Bis(benzyltripenylphosphinium)
 bis(1,2-dicyanoethene-1,2-dithiolato)nickel(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.4430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3845(5)
_cell_length_b                   14.6825(9)
_cell_length_c                   18.8748(11)
_cell_measurement_reflns_used    6873
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.49
_cell_measurement_theta_min      2.29
_cell_volume                     2565.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX 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     0.71073
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13425
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.355
_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     313
_refine_ls_number_reflns         4508
_refine_ls_number_restraints     175
_refine_ls_restrained_S_all      1.260
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0379
_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)+(0.06P)²+1.2P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1068
_reflns_number_gt                3985
_reflns_number_total             4508
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2051.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2213421
_cod_database_fobs_code          2213421
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.0000 0.0000 0.0000 0.04382(17) Uani d SU 1
P P1 0.71262(8) 0.85014(5) 0.16816(4) 0.0472(2) Uani d . 1
S S1 0.09417(8) 0.09747(6) 0.08059(4) 0.0601(2) Uani d U 1
S S2 0.17963(8) -0.09001(5) 0.03927(4) 0.0543(2) Uani d . 1
N N1 0.0244(3) 0.3313(2) 0.14578(16) 0.0726(7) Uani d U 1
N N2 0.3221(3) -0.3185(2) 0.00175(18) 0.0836(9) Uani d U 1
C C1 0.0024(3) 0.2666(2) 0.11185(16) 0.0567(6) Uani d U 1
C C2 -0.0268(3) 0.1870(2) 0.06848(15) 0.0507(6) Uani d U 1
C C3 0.1457(3) -0.1837(2) -0.01717(15) 0.0524(6) Uani d U 1
C C4 0.2437(3) -0.2583(2) -0.00691(17) 0.0602(7) Uani d U 1
C C5 0.9392(4) 0.6951(3) 0.08592(19) 0.0689(7) Uani d U 1
H H5 1.0107 0.7389 0.0976 0.083 Uiso calc R 1
C C6 0.9776(5) 0.6048(3) 0.0796(2) 0.0817(8) Uani d U 1
H H6 1.0745 0.5883 0.0867 0.098 Uiso calc R 1
C C7 0.8731(5) 0.5398(3) 0.0630(2) 0.0860(8) Uani d U 1
H H7 0.8992 0.4791 0.0594 0.103 Uiso calc R 1
C C8 0.7315(5) 0.5638(3) 0.0516(2) 0.0863(8) Uani d U 1
H H8 0.6608 0.5194 0.0401 0.104 Uiso calc R 1
C C9 0.6917(4) 0.6544(3) 0.0572(2) 0.0767(8) Uani d U 1
H H9 0.5945 0.6705 0.0490 0.092 Uiso calc R 1
C C10 0.7960(3) 0.7205(2) 0.07501(16) 0.0610(6) Uani d U 1
C C11 0.7531(4) 0.8188(2) 0.08065(16) 0.0617(7) Uani d U 1
H H11A 0.6688 0.8308 0.0447 0.074 Uiso calc R 1
H H11B 0.8309 0.8571 0.0698 0.074 Uiso calc R 1
C C12 1.0078(3) 0.8754(2) 0.21253(18) 0.0578(6) Uani d U 1
H H12 1.0159 0.8784 0.1641 0.069 Uiso calc R 1
C C13 1.1286(3) 0.8868(2) 0.2650(2) 0.0653(7) Uani d U 1
H H13 1.2186 0.8956 0.2515 0.078 Uiso calc R 1
C C14 1.1172(4) 0.8852(2) 0.3361(2) 0.0694(7) Uani d U 1
H H14 1.1990 0.8931 0.3707 0.083 Uiso calc R 1
C C15 0.9853(4) 0.8720(2) 0.35666(19) 0.0669(7) Uani d U 1
H H15 0.9777 0.8725 0.4052 0.080 Uiso calc R 1
C C16 0.8640(3) 0.8581(2) 0.30593(17) 0.0584(6) Uani d U 1
H H16 0.7751 0.8479 0.3202 0.070 Uiso calc R 1
C C17 0.8745(3) 0.8594(2) 0.23325(16) 0.0510(6) Uani d U 1
C C18 0.6183(4) 1.0140(2) 0.1030(2) 0.0703(7) Uani d U 1
H H18 0.6650 0.9969 0.0653 0.084 Uiso calc R 1
C C19 0.5460(4) 1.0968(3) 0.1017(2) 0.0792(8) Uani d U 1
H H19 0.5458 1.1359 0.0629 0.095 Uiso calc R 1
C C20 0.4756(4) 1.1214(3) 0.1563(2) 0.0786(8) Uani d U 1
H H20 0.4257 1.1763 0.1539 0.094 Uiso calc R 1
C C21 0.4778(4) 1.0661(2) 0.2145(2) 0.0744(7) Uani d U 1
H H21 0.4305 1.0837 0.2519 0.089 Uiso calc R 1
C C22 0.5501(4) 0.9838(2) 0.2180(2) 0.0644(7) Uani d U 1
H H22 0.5522 0.9463 0.2578 0.077 Uiso calc R 1
C C23 0.6193(3) 0.9575(2) 0.16196(18) 0.0572(6) Uani d U 1
C C24 0.4480(3) 0.7734(2) 0.17503(16) 0.0545(6) Uani d U 1
H H24 0.4090 0.8246 0.1499 0.065 Uiso calc R 1
C C25 0.3591(3) 0.7053(2) 0.19190(18) 0.0625(7) Uani d U 1
H H25 0.2596 0.7105 0.1782 0.075 Uiso calc R 1
C C26 0.4156(4) 0.6299(2) 0.22854(19) 0.0655(7) Uani d U 1
H H26 0.3545 0.5844 0.2400 0.079 Uiso calc R 1
C C27 0.5628(4) 0.6212(2) 0.24860(19) 0.0651(7) Uani d U 1
H H27 0.6010 0.5696 0.2733 0.078 Uiso calc R 1
C C28 0.6530(3) 0.6886(2) 0.23222(17) 0.0578(6) Uani d U 1
H H28 0.7525 0.6826 0.2457 0.069 Uiso calc R 1
C C29 0.5967(3) 0.76547(19) 0.19574(15) 0.0488(6) Uani d U 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'
P P 0.1023 0.0942 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
S1 Ni1 S1 . 3 180.00(4)
S1 Ni1 S2 . . 87.60(3)
S1 Ni1 S2 3 . 92.40(3)
S1 Ni1 S2 . 3 92.40(3)
S1 Ni1 S2 3 3 87.60(3)
S2 Ni1 S2 . 3 180.00(6)
C29 P1 C17 . . 109.94(13)
C29 P1 C23 . . 108.42(13)
C17 P1 C23 . . 109.06(15)
C29 P1 C11 . . 108.50(15)
C17 P1 C11 . . 111.25(14)
C23 P1 C11 . . 109.62(15)
C2 S1 Ni1 . . 103.05(10)
C3 S2 Ni1 . . 102.62(10)
N1 C1 C2 . . 178.9(4)
C3 C2 C1 3 . 119.9(3)
C3 C2 S1 3 . 121.0(2)
C1 C2 S1 . . 119.1(2)
C2 C3 C4 3 . 120.6(3)
C2 C3 S2 3 . 120.9(2)
C4 C3 S2 . . 118.5(2)
N2 C4 C3 . . 179.5(4)
C10 C5 C6 . . 120.5(4)
C10 C5 H5 . . 119.7
C6 C5 H5 . . 119.7
C7 C6 C5 . . 120.1(4)
C7 C6 H6 . . 120.0
C5 C6 H6 . . 120.0
C8 C7 C6 . . 120.2(4)
C8 C7 H7 . . 119.9
C6 C7 H7 . . 119.9
C7 C8 C9 . . 120.2(4)
C7 C8 H8 . . 119.9
C9 C8 H8 . . 119.9
C10 C9 C8 . . 120.2(4)
C10 C9 H9 . . 119.9
C8 C9 H9 . . 119.9
C5 C10 C9 . . 118.8(3)
C5 C10 C11 . . 121.0(3)
C9 C10 C11 . . 120.3(3)
C10 C11 P1 . . 113.9(2)
C10 C11 H11A . . 108.8
P1 C11 H11A . . 108.8
C10 C11 H11B . . 108.8
P1 C11 H11B . . 108.8
H11A C11 H11B . . 107.7
C13 C12 C17 . . 119.1(3)
C13 C12 H12 . . 120.4
C17 C12 H12 . . 120.4
C14 C13 C12 . . 120.9(3)
C14 C13 H13 . . 119.6
C12 C13 H13 . . 119.6
C13 C14 C15 . . 120.1(3)
C13 C14 H14 . . 119.9
C15 C14 H14 . . 119.9
C14 C15 C16 . . 120.4(3)
C14 C15 H15 . . 119.8
C16 C15 H15 . . 119.8
C15 C16 C17 . . 120.0(3)
C15 C16 H16 . . 120.0
C17 C16 H16 . . 120.0
C12 C17 C16 . . 119.5(3)
C12 C17 P1 . . 121.3(2)
C16 C17 P1 . . 119.0(2)
C23 C18 C19 . . 118.5(4)
C23 C18 H18 . . 120.8
C19 C18 H18 . . 120.8
C20 C19 C18 . . 120.9(4)
C20 C19 H19 . . 119.5
C18 C19 H19 . . 119.5
C19 C20 C21 . . 120.5(4)
C19 C20 H20 . . 119.8
C21 C20 H20 . . 119.8
C20 C21 C22 . . 120.1(4)
C20 C21 H21 . . 120.0
C22 C21 H21 . . 120.0
C21 C22 C23 . . 119.8(3)
C21 C22 H22 . . 120.1
C23 C22 H22 . . 120.1
C22 C23 C18 . . 120.3(3)
C22 C23 P1 . . 118.7(2)
C18 C23 P1 . . 121.0(3)
C25 C24 C29 . . 119.5(3)
C25 C24 H24 . . 120.2
C29 C24 H24 . . 120.2
C26 C25 C24 . . 120.5(3)
C26 C25 H25 . . 119.7
C24 C25 H25 . . 119.7
C25 C26 C27 . . 120.3(3)
C25 C26 H26 . . 119.9
C27 C26 H26 . . 119.9
C28 C27 C26 . . 120.0(3)
C28 C27 H27 . . 120.0
C26 C27 H27 . . 120.0
C27 C28 C29 . . 120.2(3)
C27 C28 H28 . . 119.9
C29 C28 H28 . . 119.9
C28 C29 C24 . . 119.5(3)
C28 C29 P1 . . 120.9(2)
C24 C29 P1 . . 119.4(2)
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 S1 . 2.1684(8) yes
Ni1 S1 3 2.1684(8) ?
Ni1 S2 . 2.1743(7) yes
Ni1 S2 3 2.1743(7) ?
P1 C29 . 1.785(3) ?
P1 C17 . 1.795(3) ?
P1 C23 . 1.798(3) ?
P1 C11 . 1.814(3) ?
S1 C2 . 1.727(3) yes
S2 C3 . 1.737(3) yes
N1 C1 . 1.145(4) ?
N2 C4 . 1.145(4) ?
C1 C2 . 1.428(4) ?
C2 C3 3 1.353(4) ?
C3 C2 3 1.353(4) ?
C3 C4 . 1.423(4) ?
C5 C10 . 1.377(5) ?
C5 C6 . 1.384(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.367(6) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.358(6) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.390(6) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.380(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.507(5) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.388(5) ?
C12 C17 . 1.391(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.364(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.370(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.377(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.392(4) ?
C16 H16 . 0.9300 ?
C18 C23 . 1.386(5) ?
C18 C19 . 1.391(5) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.361(6) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.363(6) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.381(5) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.384(5) ?
C22 H22 . 0.9300 ?
C24 C25 . 1.373(4) ?
C24 C29 . 1.392(4) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.365(5) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.377(5) ?
C26 H26 . 0.9300 ?
C27 C28 . 1.370(4) ?
C27 H27 . 0.9300 ?
C28 C29 . 1.381(4) ?
C28 H28 . 0.9300 ?
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
C9 H9 N2 1_565 0.93 2.57 3.478(5) 165.0 yes
C20 H20 Cg1 2_655 0.93 3.15 3.852(5) 133 yes
C27 H27 Cg1 2_645 0.93 3.17 3.727(3) 120 yes
