#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:14:52 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179237 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/57/4315749.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_4315749
loop_
_publ_author_name
'Roxanne M. Jenkins'
'Michael L. Singleton'
'Lauren A. Leamer'
'Joseph H. Reibenspies'
'Marcetta Y. Darensbourg'
_publ_section_title
;
 Orientation and Stereodynamic Paths of Planar Monodentate Ligands in
 Square Planar Nickel N2S Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5503
_journal_page_last               5514
_journal_paper_doi               10.1021/ic1002012
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C15 H29 I N4 Ni S'
_chemical_formula_weight         483.09
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 110.946(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   13.963(5)
_cell_length_b                   12.042(5)
_cell_length_c                   12.364(5)
_cell_measurement_temperature    110(2)
_cell_volume                     1941.5(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.916
_diffrn_measured_fraction_theta_max 0.916
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_av_sigmaI/netI    0.0917
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15834
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    2.699
_exptl_absorpt_correction_T_max  0.8769
_exptl_absorpt_correction_T_min  0.6569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       0.0053(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0540P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                1900
_reflns_number_total             3140
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic1002012_si_006.cif
_cod_data_source_block           rox1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4315749
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.63664(5) 0.14552(5) 0.91440(5) 0.0369(2) Uani 1 1 d . . .
Ni1 Ni 0.21866(7) 0.08736(8) 0.58955(8) 0.0227(3) Uani 1 1 d . . .
S1 S 0.11561(16) 0.20020(18) 0.46975(16) 0.0292(5) Uani 1 1 d . . .
N1 N 0.1410(5) 0.0990(6) 0.6923(5) 0.0291(16) Uani 1 1 d . . .
N2 N 0.3075(5) -0.0065(5) 0.7165(6) 0.0257(15) Uani 1 1 d . . .
N3 N 0.3739(5) 0.1567(6) 0.4993(6) 0.0312(16) Uani 1 1 d . . .
N4 N 0.2968(5) 0.0110(5) 0.4121(5) 0.0274(16) Uani 1 1 d . . .
C1 C 0.0741(6) 0.2741(7) 0.5754(7) 0.0306(19) Uani 1 1 d . . .
C2 C 0.0577(7) 0.1842(7) 0.6545(7) 0.033(2) Uani 1 1 d . . .
H2A H 0.0523 0.2201 0.7241 0.039 Uiso 1 1 calc R . .
H2B H -0.0082 0.1463 0.6133 0.039 Uiso 1 1 calc R . .
C3 C 0.0899(7) -0.0098(8) 0.6956(8) 0.040(2) Uani 1 1 d . . .
H3A H 0.0510 -0.0339 0.6153 0.048 Uiso 1 1 calc R . .
H3B H 0.0404 0.0008 0.7354 0.048 Uiso 1 1 calc R . .
C4 C 0.1645(7) -0.0993(7) 0.7564(7) 0.034(2) Uani 1 1 d . . .
H4A H 0.1898 -0.0835 0.8406 0.041 Uiso 1 1 calc R . .
H4B H 0.1270 -0.1707 0.7442 0.041 Uiso 1 1 calc R . .
C5 C 0.2534(7) -0.1133(7) 0.7212(7) 0.033(2) Uani 1 1 d . . .
H5A H 0.2305 -0.1486 0.6438 0.040 Uiso 1 1 calc R . .
H5B H 0.3027 -0.1643 0.7763 0.040 Uiso 1 1 calc R . .
C6 C 0.2200(7) 0.1221(8) 0.8083(7) 0.035(2) Uani 1 1 d . . .
H6A H 0.1953 0.0961 0.8696 0.042 Uiso 1 1 calc R . .
H6B H 0.2323 0.2031 0.8180 0.042 Uiso 1 1 calc R . .
C7 C 0.3190(7) 0.0633(7) 0.8199(7) 0.035(2) Uani 1 1 d . . .
H7A H 0.3735 0.1191 0.8298 0.042 Uiso 1 1 calc R . .
H7B H 0.3401 0.0158 0.8899 0.042 Uiso 1 1 calc R . .
C8 C 0.4105(7) -0.0344(8) 0.7166(8) 0.040(2) Uani 1 1 d . . .
H8A H 0.4476 0.0341 0.7143 0.060 Uiso 1 1 calc R . .
H8B H 0.4039 -0.0798 0.6485 0.060 Uiso 1 1 calc R . .
H8C H 0.4484 -0.0760 0.7871 0.060 Uiso 1 1 calc R . .
C9 C -0.0287(7) 0.3312(8) 0.5097(9) 0.043(2) Uani 1 1 d . . .
H9A H -0.0187 0.3881 0.4581 0.064 Uiso 1 1 calc R . .
H9B H -0.0550 0.3659 0.5652 0.064 Uiso 1 1 calc R . .
H9C H -0.0781 0.2759 0.4638 0.064 Uiso 1 1 calc R . .
C10 C 0.1510(8) 0.3585(9) 0.6413(9) 0.052(3) Uani 1 1 d . . .
H10A H 0.1586 0.4148 0.5877 0.078 Uiso 1 1 calc R . .
H10B H 0.2171 0.3222 0.6806 0.078 Uiso 1 1 calc R . .
H10C H 0.1277 0.3941 0.6988 0.078 Uiso 1 1 calc R . .
C11 C 0.2995(6) 0.0829(7) 0.4953(6) 0.0259(18) Uani 1 1 d . . .
C12 C 0.4163(6) 0.1282(7) 0.4172(7) 0.032(2) Uani 1 1 d . . .
H12 H 0.4697 0.1668 0.4024 0.039 Uiso 1 1 calc R . .
C13 C 0.3686(6) 0.0366(8) 0.3626(7) 0.032(2) Uani 1 1 d . . .
H13 H 0.3813 -0.0026 0.3025 0.039 Uiso 1 1 calc R . .
C14 C 0.4023(7) 0.2524(7) 0.5765(8) 0.036(2) Uani 1 1 d . . .
H14A H 0.4582 0.2929 0.5635 0.055 Uiso 1 1 calc R . .
H14B H 0.4251 0.2271 0.6571 0.055 Uiso 1 1 calc R . .
H14C H 0.3429 0.3015 0.5607 0.055 Uiso 1 1 calc R . .
C15 C 0.2277(8) -0.0854(7) 0.3760(7) 0.037(2) Uani 1 1 d . . .
H15A H 0.2418 -0.1257 0.3145 0.055 Uiso 1 1 calc R . .
H15B H 0.1563 -0.0598 0.3470 0.055 Uiso 1 1 calc R . .
H15C H 0.2388 -0.1347 0.4424 0.055 Uiso 1 1 calc R . .
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'
I I -0.4742 1.8119 '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
C11 Ni1 N1 176.5(3) . . ?
C11 Ni1 N2 97.5(3) . . ?
N1 Ni1 N2 82.0(3) . . ?
C11 Ni1 S1 89.6(2) . . ?
N1 Ni1 S1 90.7(2) . . ?
N2 Ni1 S1 171.97(19) . . ?
C1 S1 Ni1 96.9(3) . . ?
C6 N1 C2 113.5(6) . . ?
C6 N1 C3 109.4(7) . . ?
C2 N1 C3 106.4(7) . . ?
C6 N1 Ni1 104.4(5) . . ?
C2 N1 Ni1 113.5(5) . . ?
C3 N1 Ni1 109.6(5) . . ?
C8 N2 C7 108.8(6) . . ?
C8 N2 C5 108.0(6) . . ?
C7 N2 C5 110.5(6) . . ?
C8 N2 Ni1 117.8(5) . . ?
C7 N2 Ni1 101.7(5) . . ?
C5 N2 Ni1 109.8(5) . . ?
C11 N3 C12 109.5(7) . . ?
C11 N3 C14 124.7(7) . . ?
C12 N3 C14 125.9(7) . . ?
C11 N4 C13 111.8(7) . . ?
C11 N4 C15 125.4(7) . . ?
C13 N4 C15 122.7(7) . . ?
C10 C1 C2 112.1(8) . . ?
C10 C1 C9 109.8(8) . . ?
C2 C1 C9 109.3(7) . . ?
C10 C1 S1 111.7(6) . . ?
C2 C1 S1 105.6(5) . . ?
C9 C1 S1 108.3(6) . . ?
N1 C2 C1 114.1(7) . . ?
N1 C3 C4 112.9(8) . . ?
C5 C4 C3 116.4(7) . . ?
C4 C5 N2 113.8(7) . . ?
N1 C6 C7 109.9(6) . . ?
N2 C7 C6 111.6(7) . . ?
N4 C11 N3 105.3(6) . . ?
N4 C11 Ni1 129.4(6) . . ?
N3 C11 Ni1 125.3(6) . . ?
C13 C12 N3 107.8(7) . . ?
C12 C13 N4 105.6(7) . . ?
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 C11 1.891(8) . ?
Ni1 N1 1.947(6) . ?
Ni1 N2 1.972(7) . ?
Ni1 S1 2.142(2) . ?
S1 C1 1.837(8) . ?
N1 C6 1.490(10) . ?
N1 C2 1.495(11) . ?
N1 C3 1.499(12) . ?
N2 C8 1.476(11) . ?
N2 C7 1.490(10) . ?
N2 C5 1.504(11) . ?
N3 C11 1.354(10) . ?
N3 C12 1.389(11) . ?
N3 C14 1.458(11) . ?
N4 C11 1.334(10) . ?
N4 C13 1.383(10) . ?
N4 C15 1.473(11) . ?
C1 C10 1.492(14) . ?
C1 C2 1.530(12) . ?
C1 C9 1.536(13) . ?
C3 C4 1.501(13) . ?
C4 C5 1.464(12) . ?
C6 C7 1.512(13) . ?
C12 C13 1.340(13) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 Ni1 S1 C1 -150.3(4) . . . . ?
N1 Ni1 S1 C1 26.2(3) . . . . ?
N2 Ni1 S1 C1 1.5(15) . . . . ?
C11 Ni1 N1 C6 -35(5) . . . . ?
N2 Ni1 N1 C6 46.2(5) . . . . ?
S1 Ni1 N1 C6 -130.4(5) . . . . ?
C11 Ni1 N1 C2 89(5) . . . . ?
N2 Ni1 N1 C2 170.3(6) . . . . ?
S1 Ni1 N1 C2 -6.3(6) . . . . ?
C11 Ni1 N1 C3 -152(5) . . . . ?
N2 Ni1 N1 C3 -70.9(6) . . . . ?
S1 Ni1 N1 C3 112.5(5) . . . . ?
C11 Ni1 N2 C8 10.4(6) . . . . ?
N1 Ni1 N2 C8 -166.1(6) . . . . ?
S1 Ni1 N2 C8 -141.1(13) . . . . ?
C11 Ni1 N2 C7 129.2(5) . . . . ?
N1 Ni1 N2 C7 -47.3(5) . . . . ?
S1 Ni1 N2 C7 -22.3(18) . . . . ?
C11 Ni1 N2 C5 -113.7(5) . . . . ?
N1 Ni1 N2 C5 69.8(5) . . . . ?
S1 Ni1 N2 C5 94.8(15) . . . . ?
Ni1 S1 C1 C10 79.7(6) . . . . ?
Ni1 S1 C1 C2 -42.3(6) . . . . ?
Ni1 S1 C1 C9 -159.3(5) . . . . ?
C6 N1 C2 C1 96.3(8) . . . . ?
C3 N1 C2 C1 -143.2(7) . . . . ?
Ni1 N1 C2 C1 -22.6(9) . . . . ?
C10 C1 C2 N1 -77.4(9) . . . . ?
C9 C1 C2 N1 160.7(7) . . . . ?
S1 C1 C2 N1 44.4(8) . . . . ?
C6 N1 C3 C4 -44.4(9) . . . . ?
C2 N1 C3 C4 -167.4(7) . . . . ?
Ni1 N1 C3 C4 69.5(8) . . . . ?
N1 C3 C4 C5 -48.9(10) . . . . ?
C3 C4 C5 N2 48.4(11) . . . . ?
C8 N2 C5 C4 162.6(7) . . . . ?
C7 N2 C5 C4 43.7(9) . . . . ?
Ni1 N2 C5 C4 -67.8(8) . . . . ?
C2 N1 C6 C7 -157.6(7) . . . . ?
C3 N1 C6 C7 83.7(8) . . . . ?
Ni1 N1 C6 C7 -33.6(8) . . . . ?
C8 N2 C7 C6 163.6(7) . . . . ?
C5 N2 C7 C6 -78.1(9) . . . . ?
Ni1 N2 C7 C6 38.5(8) . . . . ?
N1 C6 C7 N2 -3.9(10) . . . . ?
C13 N4 C11 N3 0.3(9) . . . . ?
C15 N4 C11 N3 179.7(7) . . . . ?
C13 N4 C11 Ni1 179.7(6) . . . . ?
C15 N4 C11 Ni1 -0.9(12) . . . . ?
C12 N3 C11 N4 -0.1(9) . . . . ?
C14 N3 C11 N4 178.5(7) . . . . ?
C12 N3 C11 Ni1 -179.4(6) . . . . ?
C14 N3 C11 Ni1 -0.9(11) . . . . ?
N1 Ni1 C11 N4 171(5) . . . . ?
N2 Ni1 C11 N4 89.7(7) . . . . ?
S1 Ni1 C11 N4 -94.2(7) . . . . ?
N1 Ni1 C11 N3 -10(5) . . . . ?
N2 Ni1 C11 N3 -91.1(7) . . . . ?
S1 Ni1 C11 N3 85.1(7) . . . . ?
C11 N3 C12 C13 -0.2(9) . . . . ?
C14 N3 C12 C13 -178.8(8) . . . . ?
N3 C12 C13 N4 0.4(9) . . . . ?
C11 N4 C13 C12 -0.5(9) . . . . ?
C15 N4 C13 C12 -179.9(7) . . . . ?
