#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:25:49 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179327 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/24/4322408.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4322408
loop_
_publ_author_name
'Christopher E. Keefer'
'Suzanne T. Purrington'
'Robert D. Bereman'
'Paul D. Boyle'
_publ_contact_author
;
Professor Robert D. Bereman
Department of Chemistry
Box 8204
North Carolina State University
Raleigh, NC 27695-8204
USA
;
_publ_contact_author_email       R_Bereman@ncsu.edu
_publ_contact_author_fax         1(919)5155079
_publ_contact_author_phone       1(919)5151963
_publ_section_title
;
 The First Systematic Synthesis of Heterobimetallic Dithiolene-Bridged
 Complexes. Synthesis and Characterization of Metal Complexes of
 4-(1',2'-Ethylenedithiolate)-1,3-dithiole-2-one and Dimeric Metal
 Complexes of 1,2,3,4-Butadienetetrathiolate
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5437
_journal_page_last               5442
_journal_paper_doi               10.1021/ic990841a
_journal_volume                  38
_journal_year                    1999
_chemical_formula_sum            'C26 H40 N Ni O2 S8'
_chemical_formula_weight         713.78
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 99.8160(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3508(2)
_cell_length_b                   26.4703(7)
_cell_length_c                   15.2778(3)
_cell_measurement_reflns_used    5638
_cell_measurement_temperature    158(2)
_cell_measurement_theta_max      24.78
_cell_measurement_theta_min      2.59
_cell_volume                     3327.69(14)
_computing_cell_refinement       'Siemens SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      158(2)
_diffrn_measurement_device       'Siemens SMART-CCD'
_diffrn_measurement_method       '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  0.0880
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30337
_diffrn_reflns_theta_max         24.78
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    1.110
_exptl_absorpt_correction_T_max  1.065
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            grey
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       plate
_exptl_crystal_F_000             1500
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.483
_refine_diff_density_min         -0.961
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.100
_refine_ls_goodness_of_fit_obs   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         5659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_restrained_S_obs      1.189
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_obs          0.0834
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1045P)²+8.2985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2167
_refine_ls_wR_factor_obs         0.1948
_reflns_number_observed          4013
_reflns_number_total             5685
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic990841a_1.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1045P)^2^+8.2985P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1045P)^2^+8.2985P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4322408
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Ni1 Ni 1.25499(10) 0.76820(3) 1.07372(5) 0.0348(3) Uani 1 d . .
S1 S 1.1390(2) 0.75007(8) 0.94102(11) 0.0456(5) Uani 1 d . .
S2 S 1.2941(2) 0.68975(7) 1.10613(11) 0.0364(4) Uani 1 d . .
S3 S 1.3385(2) 0.78759(7) 1.21082(11) 0.0393(4) Uani 1 d . .
S4 S 1.2414(2) 0.84622(7) 1.03564(11) 0.0454(5) Uani 1 d . .
S5 S 1.2677(4) 0.50892(10) 1.0641(2) 0.0913(10) Uani 1 d . .
S6 S 1.1667(3) 0.57165(8) 0.90638(13) 0.0584(6) Uani 1 d . .
S7 S 1.2408(5) 1.02754(10) 1.0691(2) 0.1104(13) Uani 1 d . .
S8 S 1.3473(3) 0.96809(8) 1.22830(13) 0.0593(6) Uani 1 d . .
N1 N 0.6688(6) 0.1893(2) 0.2913(3) 0.0303(12) Uani 1 d . .
C1 C 1.1513(8) 0.6865(3) 0.9366(4) 0.043(2) Uani 1 d . .
H1 H 1.1108(8) 0.6698(3) 0.8824(4) 0.063(12) Uiso 1 calc R .
C2 C 1.2167(7) 0.6587(3) 1.0077(4) 0.036(2) Uani 1 d . .
C3 C 1.2234(8) 0.6034(3) 1.0076(4) 0.040(2) Uani 1 d . .
C4 C 1.2688(12) 0.5739(3) 1.0780(5) 0.064(2) Uani 1 d . .
H4 H 1.3015(12) 0.5883(3) 1.1353(5) 0.063(12) Uiso 1 calc R .
C5 C 1.1970(13) 0.5093(4) 0.9487(6) 0.070(3) Uani 1 d . .
C6 C 1.3420(8) 0.8523(3) 1.2103(4) 0.040(2) Uani 1 d . .
H6 H 1.3753(8) 0.8699(3) 1.2645(4) 0.063(12) Uiso 1 calc R .
C7 C 1.2982(8) 0.8789(3) 1.1338(4) 0.038(2) Uani 1 d . .
C8 C 1.2944(10) 0.9339(3) 1.1305(4) 0.048(2) Uani 1 d . .
C9 C 1.2446(16) 0.9624(4) 1.0595(6) 0.101(4) Uani 1 d . .
H9 H 1.2110(16) 0.9469(4) 1.0032(6) 0.063(12) Uiso 1 calc R .
C10 C 1.3139(10) 1.0296(3) 1.1843(5) 0.053(2) Uani 1 d . .
C11 C 0.7819(8) 0.1560(3) 0.2500(4) 0.036(2) Uani 1 d . .
H11A H 0.8892(8) 0.1562(3) 0.2893(4) 0.040(4) Uiso 1 calc R .
H11B H 0.7967(8) 0.1714(3) 0.1929(4) 0.040(4) Uiso 1 calc R .
C12 C 0.7321(9) 0.1016(3) 0.2323(5) 0.045(2) Uani 1 d . .
H12A H 0.6334(9) 0.1002(3) 0.1861(5) 0.040(4) Uiso 1 calc R .
H12B H 0.7054(9) 0.0863(3) 0.2872(5) 0.040(4) Uiso 1 calc R .
C13 C 0.8668(10) 0.0715(3) 0.2018(5) 0.056(2) Uani 1 d . .
H13A H 0.8896(10) 0.0862(3) 0.1456(5) 0.040(4) Uiso 1 calc R .
H13B H 0.9666(10) 0.0746(3) 0.2468(5) 0.040(4) Uiso 1 calc R .
C14 C 0.8275(13) 0.0163(3) 0.1871(6) 0.071(3) Uani 1 d . .
H14A H 0.9058(37) 0.0009(5) 0.1542(28) 0.066(7) Uiso 1 calc R .
H14B H 0.7175(25) 0.0127(3) 0.1530(27) 0.066(7) Uiso 1 calc R .
H14C H 0.8336(57) -0.0006(5) 0.2447(6) 0.066(7) Uiso 1 calc R .
C15 C 0.4994(8) 0.1901(3) 0.2345(4) 0.0331(15) Uani 1 d . .
H15A H 0.4545(8) 0.1554(3) 0.2317(4) 0.040(4) Uiso 1 calc R .
H15B H 0.4279(8) 0.2117(3) 0.2640(4) 0.040(4) Uiso 1 calc R .
C16 C 0.4946(8) 0.2093(3) 0.1397(4) 0.041(2) Uani 1 d . .
H16A H 0.5490(8) 0.2426(3) 0.1412(4) 0.040(4) Uiso 1 calc R .
H16B H 0.5537(8) 0.1855(3) 0.1067(4) 0.040(4) Uiso 1 calc R .
C17 C 0.3190(9) 0.2142(3) 0.0929(4) 0.049(2) Uani 1 d . .
H17A H 0.2624(9) 0.2388(3) 0.1256(4) 0.040(4) Uiso 1 calc R .
H17B H 0.3182(9) 0.2278(3) 0.0324(4) 0.040(4) Uiso 1 calc R .
C18 C 0.2271(10) 0.1657(3) 0.0855(6) 0.071(3) Uani 1 d . .
H18A H 0.1198(25) 0.1708(5) 0.0492(28) 0.066(7) Uiso 1 calc R .
H18B H 0.2144(51) 0.1542(10) 0.1449(7) 0.066(7) Uiso 1 calc R .
H18C H 0.2869(31) 0.1402(6) 0.0575(29) 0.066(7) Uiso 1 calc R .
C19 C 0.7445(8) 0.2414(2) 0.3005(4) 0.034(2) Uani 1 d . .
H19A H 0.8460(8) 0.2392(2) 0.3445(4) 0.040(4) Uiso 1 calc R .
H19B H 0.7756(8) 0.2504(2) 0.2428(4) 0.040(4) Uiso 1 calc R .
C20 C 0.6449(8) 0.2843(2) 0.3278(4) 0.036(2) Uani 1 d . .
H20A H 0.6144(8) 0.2768(2) 0.3862(4) 0.040(4) Uiso 1 calc R .
H20B H 0.5440(8) 0.2882(2) 0.2838(4) 0.040(4) Uiso 1 calc R .
C21 C 0.7431(8) 0.3327(2) 0.3333(5) 0.039(2) Uani 1 d . .
H21A H 0.8386(8) 0.3292(2) 0.3812(5) 0.040(4) Uiso 1 calc R .
H21B H 0.7839(8) 0.3374(2) 0.2767(5) 0.040(4) Uiso 1 calc R .
C22 C 0.6500(10) 0.3792(3) 0.3511(5) 0.056(2) Uani 1 d . .
H22A H 0.7243(15) 0.4081(5) 0.3611(32) 0.066(7) Uiso 1 calc R .
H22B H 0.6000(48) 0.3738(7) 0.4039(19) 0.066(7) Uiso 1 calc R .
H22C H 0.5650(39) 0.3861(11) 0.2998(14) 0.066(7) Uiso 1 calc R .
C23 C 0.6432(8) 0.1692(3) 0.3813(4) 0.0319(15) Uani 1 d . .
H23A H 0.5771(8) 0.1380(3) 0.3715(4) 0.040(4) Uiso 1 calc R .
H23B H 0.5792(8) 0.1944(3) 0.4087(4) 0.040(4) Uiso 1 calc R .
C24 C 0.7973(8) 0.1573(3) 0.4474(4) 0.037(2) Uani 1 d . .
H24A H 0.8578(8) 0.1298(3) 0.4236(4) 0.040(4) Uiso 1 calc R .
H24B H 0.8681(8) 0.1875(3) 0.4555(4) 0.040(4) Uiso 1 calc R .
C25 C 0.7555(8) 0.1415(3) 0.5359(4) 0.040(2) Uani 1 d . .
H25A H 0.6806(8) 0.1123(3) 0.5269(4) 0.040(4) Uiso 1 calc R .
H25B H 0.6984(8) 0.1696(3) 0.5604(4) 0.040(4) Uiso 1 calc R .
C26 C 0.9055(9) 0.1273(4) 0.6025(5) 0.056(2) Uani 1 d . .
H26A H 0.8724(9) 0.1138(17) 0.6564(13) 0.066(7) Uiso 1 calc R .
H26B H 0.9733(29) 0.1573(5) 0.6175(23) 0.066(7) Uiso 1 calc R .
H26C H 0.9677(31) 0.1016(13) 0.5765(12) 0.066(7) Uiso 1 calc R .
O1 O 1.1671(11) 0.4719(3) 0.9037(5) 0.100(3) Uani 1 d . .
O2 O 1.3290(7) 1.0672(2) 1.2274(4) 0.064(2) Uani 1 d . .
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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S4 Ni1 S1 87.97(8) . . ?
S4 Ni1 S2 173.49(8) . . ?
S1 Ni1 S2 91.60(8) . . ?
S4 Ni1 S3 91.59(8) . . ?
S1 Ni1 S3 172.21(8) . . ?
S2 Ni1 S3 89.70(7) . . ?
C1 S1 Ni1 103.9(2) . . ?
C2 S2 Ni1 103.7(3) . . ?
C6 S3 Ni1 103.7(2) . . ?
C7 S4 Ni1 104.7(3) . . ?
C4 S5 C5 96.3(4) . . ?
C3 S6 C5 97.1(4) . . ?
C9 S7 C10 96.2(4) . . ?
C8 S8 C10 98.8(4) . . ?
C11 N1 C19 106.9(5) . . ?
C11 N1 C23 111.6(5) . . ?
C19 N1 C23 110.8(5) . . ?
C11 N1 C15 110.8(5) . . ?
C19 N1 C15 111.9(5) . . ?
C23 N1 C15 105.0(4) . . ?
C2 C1 S1 122.1(6) . . ?
C1 C2 C3 123.7(6) . . ?
C1 C2 S2 118.6(6) . . ?
C3 C2 S2 117.6(5) . . ?
C4 C3 C2 126.2(6) . . ?
C4 C3 S6 115.4(6) . . ?
C2 C3 S6 118.4(5) . . ?
C3 C4 S5 119.2(6) . . ?
O1 C5 S5 124.5(8) . . ?
O1 C5 S6 123.5(8) . . ?
S5 C5 S6 111.9(5) . . ?
C7 C6 S3 121.3(5) . . ?
C6 C7 C8 123.3(6) . . ?
C6 C7 S4 118.7(6) . . ?
C8 C7 S4 118.0(5) . . ?
C9 C8 C7 126.6(7) . . ?
C9 C8 S8 113.9(7) . . ?
C7 C8 S8 119.3(5) . . ?
C8 C9 S7 120.2(7) . . ?
O2 C10 S7 124.3(6) . . ?
O2 C10 S8 124.6(6) . . ?
S7 C10 S8 110.9(5) . . ?
N1 C11 C12 117.4(5) . . ?
C11 C12 C13 111.1(6) . . ?
C14 C13 C12 113.7(7) . . ?
C16 C15 N1 114.5(5) . . ?
C17 C16 C15 109.9(6) . . ?
C18 C17 C16 113.9(7) . . ?
C20 C19 N1 118.1(5) . . ?
C19 C20 C21 109.6(5) . . ?
C22 C21 C20 114.3(6) . . ?
N1 C23 C24 115.8(5) . . ?
C25 C24 C23 110.5(5) . . ?
C24 C25 C26 112.1(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 S4 2.143(2) . ?
Ni1 S1 2.147(2) . ?
Ni1 S2 2.147(2) . ?
Ni1 S3 2.154(2) . ?
S1 C1 1.687(8) . ?
S2 C2 1.739(6) . ?
S3 C6 1.712(8) . ?
S4 C7 1.726(7) . ?
S5 C4 1.732(9) . ?
S5 C5 1.762(9) . ?
S6 C3 1.752(7) . ?
S6 C5 1.774(10) . ?
S7 C9 1.732(10) . ?
S7 C10 1.762(8) . ?
S8 C8 1.738(7) . ?
S8 C10 1.765(8) . ?
N1 C11 1.507(8) . ?
N1 C19 1.512(8) . ?
N1 C23 1.524(8) . ?
N1 C15 1.529(8) . ?
C1 C2 1.347(10) . ?
C2 C3 1.466(10) . ?
C3 C4 1.332(11) . ?
C5 O1 1.208(10) . ?
C6 C7 1.361(9) . ?
C7 C8 1.457(11) . ?
C8 C9 1.329(12) . ?
C10 O2 1.189(9) . ?
C11 C12 1.511(9) . ?
C12 C13 1.516(10) . ?
C13 C14 1.504(11) . ?
C15 C16 1.528(9) . ?
C16 C17 1.524(9) . ?
C17 C18 1.489(11) . ?
C19 C20 1.507(9) . ?
C20 C21 1.517(9) . ?
C21 C22 1.505(10) . ?
C23 C24 1.527(9) . ?
C24 C25 1.513(9) . ?
C25 C26 1.520(9) . ?
