#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:00:00 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178928 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/57/4115719.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_4115719
loop_
_publ_author_name
'Diran Herebian'
'Eberhard Bothe'
'Eckhard Bill'
'Thomas Weyhermüller'
'Karl Wieghardt'
_publ_section_title
;
 Experimental Evidence for the Noninnocence of o-Aminothiophenolates:
 Coordination Chemistry of o-Iminothionebenzosemiquinonate(1-) π-Radicals
 with Ni(II), Pd(II), Pt(II)
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10012
_journal_page_last               10023
_journal_paper_doi               10.1021/ja011155p
_journal_volume                  123
_journal_year                    2001
_chemical_formula_structural     '[C28 H42 N2 Ni S2], dmf'
_chemical_formula_sum            'C31 H49 N3 Ni O S2'
_chemical_formula_weight         602.56
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 99.25(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.666(4)
_cell_length_b                   9.7420(12)
_cell_length_c                   11.614(2)
_cell_measurement_reflns_used    3055
_cell_measurement_temperature    150(2)
_cell_volume                     3312.9(9)
_computing_cell_refinement       'Siemens SAINT'
_computing_data_collection       'Siemens SAINT'
_computing_data_reduction        'Siemens SAINT'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device       'Siemens SMART CCD-Detector'
_diffrn_measurement_method       'ω, 0.3 deg./frame'
_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  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14248
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.9563
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_type   'SADABS, G.M. Sheldrick 1994'
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       'opaque block'
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.991
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.999
_refine_ls_goodness_of_fit_obs   1.085
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_restrained_S_obs      1.085
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_obs          0.0562
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0793P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1408
_refine_ls_wR_factor_obs         0.1243
_reflns_number_observed          2575
_reflns_number_total             3765
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja011155p_1.cif
_cod_data_source_block           1a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0793P)^2^+0.0000P] 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^)+(0.0793P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3312.9(8)
_cod_database_code               4115719
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Ni1 Ni 0.5000 0.5000 0.5000 0.0245(2) Uani 1 d S
S1 S 0.44019(3) 0.53047(7) 0.37099(7) 0.0272(2) Uani 1 d .
N1 N 0.47097(9) 0.3578(3) 0.5531(2) 0.0268(6) Uani 1 d .
H1 H 0.4810(11) 0.3111(37) 0.6041(31) 0.035 Uiso 1 d .
C1 C 0.40753(10) 0.3952(3) 0.4065(2) 0.0213(6) Uani 1 d .
C2 C 0.42874(10) 0.3180(3) 0.5038(2) 0.0224(6) Uani 1 d .
C3 C 0.40651(10) 0.2047(3) 0.5457(3) 0.0240(6) Uani 1 d .
H3 H 0.42094(10) 0.1559(3) 0.6124(3) 0.029 Uiso 1 calc R
C4 C 0.36439(10) 0.1650(3) 0.4909(2) 0.0215(6) Uani 1 d .
C5 C 0.34343(10) 0.2438(3) 0.3936(3) 0.0217(6) Uani 1 d .
H5 H 0.31390(10) 0.2166(3) 0.3564(3) 0.026 Uiso 1 calc R
C6 C 0.36294(10) 0.3571(3) 0.3491(2) 0.0203(6) Uani 1 d .
C7 C 0.33709(10) 0.4366(3) 0.2446(3) 0.0270(7) Uani 1 d .
C8 C 0.32773(12) 0.5837(3) 0.2836(3) 0.0405(9) Uani 1 d .
H8A H 0.31026(12) 0.5800(3) 0.3484(3) 0.061 Uiso 1 calc R
H8B H 0.31020(12) 0.6339(3) 0.2181(3) 0.061 Uiso 1 calc R
H8C H 0.35681(12) 0.6309(3) 0.3092(3) 0.061 Uiso 1 calc R
C9 C 0.29037(10) 0.3720(3) 0.1975(3) 0.0316(7) Uani 1 d .
H9A H 0.27183(10) 0.3679(3) 0.2600(3) 0.047 Uiso 1 calc R
H9B H 0.29487(10) 0.2790(3) 0.1692(3) 0.047 Uiso 1 calc R
H9C H 0.27470(10) 0.4281(3) 0.1332(3) 0.047 Uiso 1 calc R
C10 C 0.36433(11) 0.4402(4) 0.1437(3) 0.0348(8) Uani 1 d .
H10A H 0.34716(11) 0.4913(4) 0.0783(3) 0.052 Uiso 1 calc R
H10B H 0.36958(11) 0.3462(4) 0.1188(3) 0.052 Uiso 1 calc R
H10C H 0.39375(11) 0.4854(4) 0.1693(3) 0.052 Uiso 1 calc R
C11 C 0.33966(10) 0.0405(3) 0.5308(3) 0.0247(7) Uani 1 d .
C12 C 0.36727(12) -0.0252(3) 0.6401(3) 0.0389(9) Uani 1 d .
H12A H 0.35060(12) -0.1046(3) 0.6636(3) 0.058 Uiso 1 calc R
H12B H 0.37184(12) 0.0421(3) 0.7035(3) 0.058 Uiso 1 calc R
H12C H 0.39700(12) -0.0552(3) 0.6228(3) 0.058 Uiso 1 calc R
C13 C 0.33307(11) -0.0682(3) 0.4337(3) 0.0307(7) Uani 1 d .
H13A H 0.31720(11) -0.1480(3) 0.4595(3) 0.046 Uiso 1 calc R
H13B H 0.36295(11) -0.0967(3) 0.4163(3) 0.046 Uiso 1 calc R
H13C H 0.31487(11) -0.0294(3) 0.3634(3) 0.046 Uiso 1 calc R
C14 C 0.29287(11) 0.0826(3) 0.5584(3) 0.0350(8) Uani 1 d .
H14A H 0.27739(11) 0.0019(3) 0.5839(3) 0.053 Uiso 1 calc R
H14B H 0.27443(11) 0.1213(3) 0.4884(3) 0.053 Uiso 1 calc R
H14C H 0.29683(11) 0.1516(3) 0.6207(3) 0.053 Uiso 1 calc R
O20 O 0.5000 0.1491(4) 0.7500 0.086(2) Uani 1 d S
C21 C 0.4886(2) 0.0262(8) 0.7889(6) 0.040(2) Uani 0.50 d P
H21 H 0.4708(2) 0.0230(8) 0.8499(6) 0.048 Uiso 0.50 calc PR
N22 N 0.5000 -0.0786(5) 0.7500 0.066(2) Uani 1 d S
C23 C 0.5000 -0.2225(6) 0.7500 0.094(3) Uani 1 d S
H23A H 0.5173 -0.2560(6) 0.6906 0.141 Uiso 0.50 calc PR
H23B H 0.4685 -0.2560(6) 0.7324 0.141 Uiso 0.50 calc PR
H23C H 0.5142 -0.2560(6) 0.8269 0.141 Uiso 0.50 calc PR
C24 C 0.5251(3) -0.0530(9) 0.6329(8) 0.066(3) Uani 0.50 d P
H24A H 0.5340(3) -0.1416(9) 0.6034(8) 0.099 Uiso 0.50 calc PR
H24B H 0.5523(3) 0.0042(9) 0.6545(8) 0.099 Uiso 0.50 calc PR
H24C H 0.5037(3) -0.0066(9) 0.5722(8) 0.099 Uiso 0.50 calc PR
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
N1 Ni1 N1 179.997(1) . 5_666
N1 Ni1 S1 87.59(8) . .
N1 Ni1 S1 92.41(8) 5_666 .
N1 Ni1 S1 92.41(8) . 5_666
N1 Ni1 S1 87.59(8) 5_666 5_666
S1 Ni1 S1 180.0 . 5_666
C1 S1 Ni1 99.23(10) . .
C2 N1 Ni1 122.8(2) . .
C2 C1 C6 119.4(2) . .
C2 C1 S1 113.7(2) . .
C6 C1 S1 126.9(2) . .
N1 C2 C3 122.2(3) . .
N1 C2 C1 116.6(3) . .
C3 C2 C1 121.2(3) . .
C4 C3 C2 120.3(3) . .
C3 C4 C5 117.9(3) . .
C3 C4 C11 122.1(3) . .
C5 C4 C11 120.0(2) . .
C6 C5 C4 124.8(3) . .
C5 C6 C1 116.4(3) . .
C5 C6 C7 120.7(3) . .
C1 C6 C7 122.9(2) . .
C10 C7 C6 111.1(2) . .
C10 C7 C9 107.1(3) . .
C6 C7 C9 112.4(2) . .
C10 C7 C8 110.3(3) . .
C6 C7 C8 109.1(2) . .
C9 C7 C8 106.8(2) . .
C4 C11 C14 110.3(2) . .
C4 C11 C12 111.3(2) . .
C14 C11 C12 108.7(3) . .
C4 C11 C13 109.6(2) . .
C14 C11 C13 109.0(2) . .
C12 C11 C13 107.9(3) . .
N22 C21 O20 122.5(6) . .
C21 N22 C23 149.3(4) . .
C21 N22 C24 111.9(5) . .
C23 N22 C24 98.6(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 1.792(3) .
Ni1 N1 1.792(3) 5_666
Ni1 S1 2.1509(9) .
Ni1 S1 2.1510(9) 5_666
S1 C1 1.724(3) .
N1 C2 1.348(4) .
C1 C2 1.418(4) .
C1 C6 1.431(4) .
C2 C3 1.411(4) .
C3 C4 1.364(4) .
C4 C5 1.424(4) .
C4 C11 1.527(4) .
C5 C6 1.384(4) .
C6 C7 1.537(4) .
C7 C10 1.527(4) .
C7 C9 1.540(4) .
C7 C8 1.542(4) .
C11 C14 1.530(4) .
C11 C12 1.535(4) .
C11 C13 1.537(4) .
O20 C21 1.342(8) .
C21 N22 1.187(8) .
N22 C23 1.402(7) .
N22 C24 1.670(8) .
