#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:26:16 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179790 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/86/7008604.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_7008604
loop_
_publ_author_name
'Lewis, Jana A.'
'Tran, Ba L.'
'Puerta, David T.'
'Rumberger, Evan M.'
'Hendrickson, David N.'
'Cohen, Seth M.'
_publ_section_title
;
 Synthesis, structure and spectroscopy of new thiopyrone and
 hydroxypyridinethione transition-metal complexes.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2588
_journal_page_last               2596
_journal_paper_doi               10.1039/b505034k
_journal_year                    2005
_chemical_formula_sum            'C15 H20 N2 Ni O3 S2'
_chemical_formula_weight         399.16
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.4626(7)
_cell_length_b                   19.3473(18)
_cell_length_c                   22.730(2)
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      1.79
_cell_volume                     3281.8(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            26647
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    1.452
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.785266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0462
_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)+(0.0404P)²+1.9028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                3025
_reflns_number_total             3766
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b505034k.txt
_cod_data_source_block           '[Ni(3,4-HOPTO)2]'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7008604
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
Ni1 Ni 0.09529(5) 0.349914(18) 0.397950(15) 0.01156(11) Uani 1 1 d . . .
S1 S 0.09408(10) 0.34968(4) 0.49291(3) 0.01507(16) Uani 1 1 d . . .
S2 S -0.03478(10) 0.25099(4) 0.39579(3) 0.01444(16) Uani 1 1 d . . .
O1 O 0.2114(3) 0.43637(10) 0.39807(8) 0.0140(4) Uani 1 1 d . . .
O2 O 0.0966(3) 0.35297(10) 0.31536(8) 0.0159(4) Uani 1 1 d . . .
O3 O 1.0472(3) 0.52675(13) 0.31565(11) 0.0271(6) Uani 1 1 d . . .
N1 N -0.0316(3) 0.23658(12) 0.19924(10) 0.0126(5) Uani 1 1 d . . .
N2 N 0.3131(3) 0.56455(12) 0.50712(10) 0.0133(5) Uani 1 1 d . . .
C1 C 0.1741(4) 0.43289(15) 0.50152(12) 0.0126(6) Uani 1 1 d . . .
C2 C 0.1850(4) 0.46793(15) 0.55490(12) 0.0148(6) Uani 1 1 d . . .
H2 H 0.1449 0.4464 0.5901 0.018 Uiso 1 1 calc R . .
C3 C 0.2534(4) 0.53329(15) 0.55645(12) 0.0164(6) Uani 1 1 d . . .
H3A H 0.2590 0.5572 0.5929 0.020 Uiso 1 1 calc R . .
C4 C 0.3813(4) 0.63583(15) 0.51195(13) 0.0179(7) Uani 1 1 d . . .
H4A H 0.3561 0.6538 0.5514 0.027 Uiso 1 1 calc R . .
H4B H 0.3221 0.6650 0.4826 0.027 Uiso 1 1 calc R . .
H4C H 0.5109 0.6361 0.5051 0.027 Uiso 1 1 calc R . .
C5 C 0.3054(3) 0.53297(14) 0.45377(12) 0.0116(6) Uani 1 1 d . . .
C6 C 0.3733(4) 0.56953(15) 0.40031(12) 0.0160(6) Uani 1 1 d . . .
H6A H 0.2839 0.6032 0.3871 0.024 Uiso 1 1 calc R . .
H6B H 0.3951 0.5358 0.3689 0.024 Uiso 1 1 calc R . .
H6C H 0.4853 0.5935 0.4098 0.024 Uiso 1 1 calc R . .
C7 C 0.2304(4) 0.46706(15) 0.44948(12) 0.0125(6) Uani 1 1 d . . .
C8 C -0.0334(4) 0.24127(15) 0.32024(12) 0.0148(6) Uani 1 1 d . . .
C9 C -0.0943(4) 0.18301(15) 0.28996(13) 0.0167(6) Uani 1 1 d . . .
H9 H -0.1389 0.1443 0.3112 0.020 Uiso 1 1 calc R . .
C10 C -0.0900(4) 0.18161(15) 0.23009(13) 0.0159(6) Uani 1 1 d . . .
H10 H -0.1286 0.1413 0.2098 0.019 Uiso 1 1 calc R . .
C11 C -0.0278(4) 0.23194(16) 0.13426(12) 0.0184(7) Uani 1 1 d . . .
H11A H -0.0697 0.1862 0.1220 0.028 Uiso 1 1 calc R . .
H11B H 0.0950 0.2391 0.1203 0.028 Uiso 1 1 calc R . .
H11C H -0.1063 0.2675 0.1175 0.028 Uiso 1 1 calc R . .
C12 C 0.0281(4) 0.29541(14) 0.22612(12) 0.0125(6) Uani 1 1 d . . .
C13 C 0.0857(4) 0.35514(15) 0.18929(12) 0.0157(6) Uani 1 1 d . . .
H13A H 0.1824 0.3406 0.1629 0.024 Uiso 1 1 calc R . .
H13B H 0.1287 0.3925 0.2148 0.024 Uiso 1 1 calc R . .
H13C H -0.0161 0.3717 0.1660 0.024 Uiso 1 1 calc R . .
C14 C 0.0331(4) 0.29824(14) 0.28737(12) 0.0127(6) Uani 1 1 d . . .
C15 C 0.8944(4) 0.50924(17) 0.28199(14) 0.0252(7) Uani 1 1 d . . .
H15A H 0.7892 0.5070 0.3077 0.038 Uiso 1 1 calc R . .
H15B H 0.9130 0.4642 0.2633 0.038 Uiso 1 1 calc R . .
H15C H 0.8750 0.5444 0.2516 0.038 Uiso 1 1 calc R . .
H3B H 1.080(5) 0.496(2) 0.3312(17) 0.033(12) Uiso 1 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
O2 Ni1 O1 88.34(8) . . ?
O2 Ni1 S2 90.44(6) . . ?
O1 Ni1 S2 178.68(6) . . ?
O2 Ni1 S1 178.32(6) . . ?
O1 Ni1 S1 90.13(6) . . ?
S2 Ni1 S1 91.09(3) . . ?
C1 S1 Ni1 96.31(10) . . ?
C8 S2 Ni1 96.72(10) . . ?
C7 O1 Ni1 116.78(17) . . ?
C14 O2 Ni1 116.97(18) . . ?
C10 N1 C12 122.0(2) . . ?
C10 N1 C11 118.6(2) . . ?
C12 N1 C11 119.4(2) . . ?
C3 N2 C5 121.7(2) . . ?
C3 N2 C4 118.1(2) . . ?
C5 N2 C4 120.1(2) . . ?
C2 C1 C7 118.9(3) . . ?
C2 C1 S1 124.9(2) . . ?
C7 C1 S1 116.2(2) . . ?
C3 C2 C1 119.7(3) . . ?
N2 C3 C2 121.2(3) . . ?
N2 C5 C7 119.3(2) . . ?
N2 C5 C6 119.9(2) . . ?
C7 C5 C6 120.8(2) . . ?
O1 C7 C5 121.1(2) . . ?
O1 C7 C1 119.8(3) . . ?
C5 C7 C1 119.1(3) . . ?
C9 C8 C14 118.7(3) . . ?
C9 C8 S2 125.2(2) . . ?
C14 C8 S2 116.1(2) . . ?
C10 C9 C8 120.1(3) . . ?
N1 C10 C9 120.8(3) . . ?
N1 C12 C14 119.2(3) . . ?
N1 C12 C13 119.3(2) . . ?
C14 C12 C13 121.5(3) . . ?
O2 C14 C12 121.4(3) . . ?
O2 C14 C8 119.5(3) . . ?
C12 C14 C8 119.0(3) . . ?
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 O2 1.8782(19) . ?
Ni1 O1 1.8840(19) . ?
Ni1 S2 2.1466(8) . ?
Ni1 S1 2.1584(8) . ?
S1 C1 1.728(3) . ?
S2 C8 1.728(3) . ?
O1 C7 1.318(3) . ?
O2 C14 1.323(3) . ?
O3 C15 1.415(4) . ?
N1 C10 1.347(4) . ?
N1 C12 1.366(3) . ?
N1 C11 1.480(3) . ?
N2 C3 1.350(4) . ?
N2 C5 1.359(3) . ?
N2 C4 1.474(4) . ?
C1 C2 1.392(4) . ?
C1 C7 1.419(4) . ?
C2 C3 1.364(4) . ?
C5 C7 1.396(4) . ?
C5 C6 1.494(4) . ?
C8 C9 1.397(4) . ?
C8 C14 1.421(4) . ?
C9 C10 1.361(4) . ?
C12 C14 1.394(4) . ?
C12 C13 1.490(4) . ?
