#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/61/2216130.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_2216130
loop_
_publ_author_name
'Yong Hou'
'Hongrong Zuo'
'Qian Huang'
'Chunlin Ni'
_publ_section_title
;
 Bis(piperidinium)
 bis(1,2-dicyanoethene-1,2-dithiolato-κ²S,S')nickel(II)
;
_journal_coeditor_code           SJ2375
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2802
_journal_page_last               m2802
_journal_paper_doi               10.1107/S1600536807050362
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '(C5 H12 N)2 [Ni (C4 N2 S2)2]'
_chemical_formula_moiety         '2C5 H12 N + , C8 N4 Ni S4 2-'
_chemical_formula_sum            'C18 H24 N6 Ni S4'
_chemical_formula_weight         511.38
_chemical_name_systematic
;
Bis(piperidinium) bis(1,2-dicyanoethene-1,2-dithiolato-κ²S,S')nickel(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                91.477(2)
_cell_angle_beta                 100.083(2)
_cell_angle_gamma                100.425(2)
_cell_formula_units_Z            1
_cell_length_a                   6.5959(9)
_cell_length_b                   9.4351(13)
_cell_length_c                   9.5669(13)
_cell_measurement_reflns_used    2647
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.78
_cell_measurement_theta_min      2.99
_cell_volume                     575.49(14)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXTL (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3282
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.223
_exptl_absorpt_correction_T_max  0.736
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             266
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.452
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0351
_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)+(0.0671P)²+0.3691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                2105
_reflns_number_total             2213
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2375.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               2216130
_cod_database_fobs_code          2216130
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 0.5000 0.5000 0.0000 0.02917(16) Uani d S 1
S S1 0.67713(10) 0.37773(7) 0.15080(7) 0.03905(19) Uani d . 1
S S2 0.24609(10) 0.48199(7) 0.11978(7) 0.03761(19) Uani d . 1
N N1 0.6624(5) 0.2290(3) 0.5088(3) 0.0610(7) Uani d . 1
N N2 0.1297(5) 0.3650(4) 0.4721(3) 0.0616(7) Uani d . 1
N N3 0.0823(6) -0.0310(4) 0.7782(5) 0.0899(12) Uani d . 1
H H3A 0.1473 -0.0330 0.8688 0.108 Uiso calc R 1
H H3B 0.0572 -0.1212 0.7379 0.108 Uiso calc R 1
C C1 0.6037(4) 0.2850(3) 0.4081(3) 0.0421(6) Uani d . 1
C C2 0.5287(4) 0.3541(3) 0.2844(3) 0.0351(5) Uani d . 1
C C3 0.3420(4) 0.4004(3) 0.2707(3) 0.0337(5) Uani d . 1
C C4 0.2229(4) 0.3819(3) 0.3816(3) 0.0406(6) Uani d . 1
C C5 0.2229(6) 0.0684(4) 0.6987(4) 0.0632(9) Uani d . 1
H H5A 0.3568 0.0376 0.7062 0.076 Uiso calc R 1
H H5B 0.1593 0.0629 0.5988 0.076 Uiso calc R 1
C C6 0.2571(5) 0.2211(3) 0.7584(3) 0.0522(7) Uani d . 1
H H6A 0.3318 0.2282 0.8558 0.063 Uiso calc R 1
H H6B 0.3422 0.2840 0.7035 0.063 Uiso calc R 1
C C7 0.0525(4) 0.2688(2) 0.7541(3) 0.0342(5) Uani d . 1
H H7A 0.0782 0.3669 0.7951 0.041 Uiso calc R 1
H H7B -0.0164 0.2688 0.6558 0.041 Uiso calc R 1
C C8 -0.0891(6) 0.1742(3) 0.8328(4) 0.0529(7) Uani d . 1
H H8A -0.2225 0.2059 0.8229 0.063 Uiso calc R 1
H H8B -0.0274 0.1813 0.9331 0.063 Uiso calc R 1
C C9 -0.1238(6) 0.0194(3) 0.7759(4) 0.0585(8) Uani d . 1
H H9A -0.2014 0.0105 0.6791 0.070 Uiso calc R 1
H H9B -0.2073 -0.0418 0.8330 0.070 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Ni1 0.0303(3) 0.0321(3) 0.0261(2) 0.00943(17) 0.00428(17) 0.00203(16)
S1 0.0389(4) 0.0475(4) 0.0374(4) 0.0201(3) 0.0110(3) 0.0122(3)
S2 0.0332(3) 0.0502(4) 0.0334(3) 0.0160(3) 0.0073(2) 0.0092(3)
N1 0.0587(16) 0.0760(19) 0.0519(16) 0.0217(14) 0.0072(13) 0.0293(14)
N2 0.0522(15) 0.092(2) 0.0470(15) 0.0183(15) 0.0201(13) 0.0165(14)
N3 0.100(3) 0.0516(18) 0.115(3) 0.0232(18) 0.002(2) -0.0007(18)
C1 0.0385(14) 0.0478(15) 0.0418(15) 0.0110(11) 0.0078(11) 0.0114(12)
C2 0.0370(13) 0.0361(12) 0.0326(12) 0.0084(10) 0.0057(10) 0.0062(9)
C3 0.0336(12) 0.0365(12) 0.0302(12) 0.0060(10) 0.0042(9) 0.0032(9)
C4 0.0367(13) 0.0500(15) 0.0355(14) 0.0100(11) 0.0055(11) 0.0064(11)
C5 0.059(2) 0.0600(19) 0.071(2) 0.0180(16) 0.0084(17) -0.0130(16)
C6 0.0488(17) 0.0530(17) 0.0501(17) 0.0038(13) 0.0030(13) -0.0016(13)
C7 0.0465(14) 0.0247(11) 0.0308(12) 0.0076(10) 0.0049(10) 0.0020(8)
C8 0.064(2) 0.0479(16) 0.0532(17) 0.0147(14) 0.0234(15) 0.0085(13)
C9 0.063(2) 0.0414(15) 0.068(2) 0.0025(14) 0.0093(16) 0.0082(14)
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'
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
S2 Ni1 S2 2_665 . 180.00(4)
S2 Ni1 S1 2_665 2_665 92.32(2)
S2 Ni1 S1 . 2_665 87.68(2)
S2 Ni1 S1 2_665 . 87.68(2)
S2 Ni1 S1 . . 92.32(2)
S1 Ni1 S1 2_665 . 180.00(3)
C2 S1 Ni1 . . 102.68(9)
C3 S2 Ni1 . . 102.88(9)
C5 N3 C9 . . 110.8(3)
C5 N3 H3A . . 109.5
C9 N3 H3A . . 109.5
C5 N3 H3B . . 109.5
C9 N3 H3B . . 109.5
H3A N3 H3B . . 108.1
N1 C1 C2 . . 179.3(3)
C3 C2 C1 . . 120.4(2)
C3 C2 S1 . . 120.59(19)
C1 C2 S1 . . 119.0(2)
C2 C3 C4 . . 120.1(2)
C2 C3 S2 . . 121.05(19)
C4 C3 S2 . . 118.9(2)
N2 C4 C3 . . 178.5(3)
C6 C5 N3 . . 110.6(3)
C6 C5 H5A . . 109.5
N3 C5 H5A . . 109.5
C6 C5 H5B . . 109.5
N3 C5 H5B . . 109.5
H5A C5 H5B . . 108.1
C7 C6 C5 . . 110.6(3)
C7 C6 H6A . . 109.5
C5 C6 H6A . . 109.5
C7 C6 H6B . . 109.5
C5 C6 H6B . . 109.5
H6A C6 H6B . . 108.1
C8 C7 C6 . . 112.4(2)
C8 C7 H7A . . 109.1
C6 C7 H7A . . 109.1
C8 C7 H7B . . 109.1
C6 C7 H7B . . 109.1
H7A C7 H7B . . 107.9
C7 C8 C9 . . 110.3(3)
C7 C8 H8A . . 109.6
C9 C8 H8A . . 109.6
C7 C8 H8B . . 109.6
C9 C8 H8B . . 109.6
H8A C8 H8B . . 108.1
C8 C9 N3 . . 111.4(3)
C8 C9 H9A . . 109.3
N3 C9 H9A . . 109.3
C8 C9 H9B . . 109.3
N3 C9 H9B . . 109.3
H9A C9 H9B . . 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ni1 S2 2_665 2.1739(7)
Ni1 S2 . 2.1739(7)
Ni1 S1 2_665 2.1819(6)
Ni1 S1 . 2.1819(6)
S1 C2 . 1.737(3)
S2 C3 . 1.730(3)
N1 C1 . 1.151(4)
N2 C4 . 1.145(4)
N3 C5 . 1.512(5)
N3 C9 . 1.517(5)
N3 H3A . 0.9000
N3 H3B . 0.9000
C1 C2 . 1.422(4)
C2 C3 . 1.366(4)
C3 C4 . 1.422(4)
C5 C6 . 1.500(4)
C5 H5A . 0.9700
C5 H5B . 0.9700
C6 C7 . 1.492(4)
C6 H6A . 0.9700
C6 H6B . 0.9700
C7 C8 . 1.489(4)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 C9 . 1.508(4)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 H9A . 0.9700
C9 H9B . 0.9700
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
C6 H6B N2 ? 0.970 2.610 3.139(4) 114.0 y
C7 H7B N2 ? 0.970 2.280 2.967(4) 127.0 y
C7 H7A S1 2_666 0.970 2.630 3.501(3) 150.0 y
C7 H7B N1 1_455 0.970 2.290 3.124(4) 143.0 y
C6 H6A Ni1 ? 0.97 Missing Missing Missing y
