#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/27/4342789.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_4342789
loop_
_publ_author_name
'Broering, Ellen P.'
'Dillon, Stephanie'
'Gale, Eric M.'
'Steiner, Ramsey A.'
'Telser, Joshua'
'Brunold, Thomas C.'
'Harrop, Todd C.'
_publ_section_title
;
 Accessing Ni(III)-Thiolate Versus Ni(II)-Thiyl Bonding in a Family of
 Ni-N2S2 Synthetic Models of NiSOD.
;
_journal_issue                   8
_journal_name_full               'Inorganic chemistry'
_journal_page_first              3815
_journal_page_last               3828
_journal_paper_doi               10.1021/ic503124f
_journal_volume                  54
_journal_year                    2015
_chemical_formula_sum            'C22 H34 N4 Ni O S2'
_chemical_formula_weight         493.36
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.038(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5155(19)
_cell_length_b                   10.0686(16)
_cell_length_c                   20.095(3)
_cell_measurement_reflns_used    9823
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.36
_cell_measurement_theta_min      2.26
_cell_volume                     2328.4(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER SMART APEX-II CCD'
_diffrn_measurement_method       'OMEGA SCAN'
_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  0.0643
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            34465
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    1.034
_exptl_absorpt_correction_T_max  0.9696
_exptl_absorpt_correction_T_min  0.7467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         6815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0378
_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)+(0.0446P)²+0.5915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                5138
_reflns_number_total             6815
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic503124f_si_003.cif
_cod_data_source_block           j1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4342789--4342791.cif.
;
_cod_original_cell_volume        2328.4(7)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4342789
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ni1 Ni 1.04943(2) 0.66109(2) 0.201352(11) 0.01693(7) Uani 1 1 d .
S1 S 1.01799(5) 0.45406(5) 0.21622(3) 0.02395(11) Uani 1 1 d .
S2 S 0.99695(4) 0.64159(5) 0.09456(2) 0.01921(10) Uani 1 1 d .
N1 N 1.09114(14) 0.67505(15) 0.29213(8) 0.0178(3) Uani 1 1 d .
N2 N 1.08308(14) 0.85006(15) 0.20115(8) 0.0180(3) Uani 1 1 d .
N3 N 0.85190(15) 0.67655(16) -0.03263(8) 0.0223(3) Uani 1 1 d .
H3A H 0.8140 0.6805 -0.0714 0.027 Uiso 1 1 calc R
H3B H 0.9202 0.6375 -0.0294 0.027 Uiso 1 1 calc R
O1 O 1.13444(13) 0.82644(14) 0.37622(7) 0.0251(3) Uani 1 1 d .
C1 C 1.09191(17) 0.43448(19) 0.29821(10) 0.0221(4) Uani 1 1 d .
H1A H 1.0550 0.3617 0.3229 0.027 Uiso 1 1 calc R
H1B H 1.1743 0.4107 0.2924 0.027 Uiso 1 1 calc R
C2 C 1.08509(17) 0.56243(19) 0.33771(9) 0.0211(4) Uani 1 1 d .
H2A H 1.0113 0.5654 0.3615 0.025 Uiso 1 1 calc R
H2B H 1.1502 0.5667 0.3711 0.025 Uiso 1 1 calc R
C3 C 1.11406(16) 0.79465(19) 0.31674(9) 0.0190(4) Uani 1 1 d .
C4 C 1.11245(16) 0.89781(19) 0.26259(9) 0.0175(4) Uani 1 1 d .
C5 C 1.13867(17) 1.0304(2) 0.27412(10) 0.0222(4) Uani 1 1 d .
H5A H 1.1588 1.0609 0.3178 0.027 Uiso 1 1 calc R
C6 C 1.13490(17) 1.1178(2) 0.22068(10) 0.0233(4) Uani 1 1 d .
H6A H 1.1522 1.2093 0.2272 0.028 Uiso 1 1 calc R
C7 C 1.10543(16) 1.06953(19) 0.15759(10) 0.0222(4) Uani 1 1 d .
H7A H 1.1028 1.1274 0.1202 0.027 Uiso 1 1 calc R
C8 C 1.07986(17) 0.93534(19) 0.14984(10) 0.0206(4) Uani 1 1 d .
H8A H 1.0593 0.9029 0.1066 0.025 Uiso 1 1 calc R
C9 C 0.86345(16) 0.72877(18) 0.08623(9) 0.0180(4) Uani 1 1 d .
C10 C 0.81059(17) 0.78899(19) 0.14046(9) 0.0195(4) Uani 1 1 d .
H10A H 0.8499 0.7881 0.1828 0.023 Uiso 1 1 calc R
C11 C 0.70262(17) 0.84980(18) 0.13404(10) 0.0210(4) Uani 1 1 d .
H11A H 0.6689 0.8899 0.1715 0.025 Uiso 1 1 calc R
C12 C 0.64432(18) 0.85162(19) 0.07238(10) 0.0220(4) Uani 1 1 d .
H12A H 0.5700 0.8922 0.0676 0.026 Uiso 1 1 calc R
C13 C 0.69490(17) 0.79394(19) 0.01780(10) 0.0218(4) Uani 1 1 d .
H13A H 0.6549 0.7965 -0.0244 0.026 Uiso 1 1 calc R
C14 C 0.80377(17) 0.73205(18) 0.02355(9) 0.0186(4) Uani 1 1 d .
N4 N 0.76768(14) 0.79174(16) 0.41563(8) 0.0209(3) Uani 1 1 d .
C15 C 0.7112(2) 0.6880(2) 0.30243(10) 0.0289(5) Uani 1 1 d .
H15A H 0.7398 0.6260 0.2691 0.043 Uiso 1 1 calc R
H15B H 0.6994 0.7756 0.2821 0.043 Uiso 1 1 calc R
H15C H 0.6374 0.6553 0.3189 0.043 Uiso 1 1 calc R
C16 C 0.79940(17) 0.69873(19) 0.35986(10) 0.0220(4) Uani 1 1 d .
H16A H 0.8120 0.6090 0.3789 0.026 Uiso 1 1 calc R
H16B H 0.8741 0.7286 0.3421 0.026 Uiso 1 1 calc R
C17 C 0.63367(19) 0.6189(2) 0.46656(10) 0.0273(4) Uani 1 1 d .
H17A H 0.5543 0.6070 0.4815 0.041 Uiso 1 1 calc R
H17B H 0.6889 0.6037 0.5040 0.041 Uiso 1 1 calc R
H17C H 0.6486 0.5555 0.4309 0.041 Uiso 1 1 calc R
C18 C 0.64796(17) 0.7590(2) 0.44076(10) 0.0228(4) Uani 1 1 d .
H18A H 0.6304 0.8219 0.4769 0.027 Uiso 1 1 calc R
H18B H 0.5898 0.7738 0.4040 0.027 Uiso 1 1 calc R
C19 C 0.86988(19) 0.9853(2) 0.35893(13) 0.0331(5) Uani 1 1 d .
H19A H 0.8582 1.0778 0.3451 0.050 Uiso 1 1 calc R
H19B H 0.8849 0.9306 0.3198 0.050 Uiso 1 1 calc R
H19C H 0.9364 0.9799 0.3906 0.050 Uiso 1 1 calc R
C20 C 0.76165(18) 0.93504(19) 0.39187(11) 0.0264(4) Uani 1 1 d .
H20A H 0.6948 0.9441 0.3598 0.032 Uiso 1 1 calc R
H20B H 0.7465 0.9927 0.4305 0.032 Uiso 1 1 calc R
C21 C 0.8473(2) 0.8573(3) 0.53217(13) 0.0437(6) Uani 1 1 d .
H21A H 0.9116 0.8388 0.5641 0.066 Uiso 1 1 calc R
H21B H 0.7734 0.8352 0.5522 0.066 Uiso 1 1 calc R
H21C H 0.8478 0.9517 0.5202 0.066 Uiso 1 1 calc R
C22 C 0.86154(18) 0.7738(2) 0.46999(10) 0.0279(4) Uani 1 1 d .
H22A H 0.9376 0.7954 0.4512 0.033 Uiso 1 1 calc R
H22B H 0.8636 0.6791 0.4831 0.033 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'
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
N1 Ni1 N2 83.36(7)
N1 Ni1 S1 88.62(5)
N2 Ni1 S1 171.97(5)
N1 Ni1 S2 178.74(5)
N2 Ni1 S2 97.60(5)
S1 Ni1 S2 90.41(2)
C1 S1 Ni1 98.88(6)
C9 S2 Ni1 104.66(6)
C3 N1 C2 119.01(16)
C3 N1 Ni1 118.16(13)
C2 N1 Ni1 122.38(12)
C8 N2 C4 118.17(16)
C8 N2 Ni1 128.96(13)
C4 N2 Ni1 112.87(12)
C2 C1 S1 110.31(13)
N1 C2 C1 109.07(15)
O1 C3 N1 128.10(18)
O1 C3 C4 120.76(17)
N1 C3 C4 111.14(16)
N2 C4 C5 122.62(17)
N2 C4 C3 114.20(16)
C5 C4 C3 123.18(17)
C4 C5 C6 118.74(18)
C7 C6 C5 118.95(18)
C6 C7 C8 119.12(18)
N2 C8 C7 122.40(18)
C10 C9 C14 118.08(17)
C10 C9 S2 122.59(14)
C14 C9 S2 119.23(14)
C11 C10 C9 122.00(17)
C12 C11 C10 119.47(18)
C11 C12 C13 119.79(19)
C12 C13 C14 121.36(18)
N3 C14 C13 119.50(17)
N3 C14 C9 121.20(17)
C13 C14 C9 119.29(17)
C16 N4 C22 105.92(15)
C16 N4 C20 111.34(15)
C22 N4 C20 111.20(16)
C16 N4 C18 110.91(15)
C22 N4 C18 111.44(16)
C20 N4 C18 106.14(14)
N4 C16 C15 115.80(16)
C17 C18 N4 115.24(16)
C19 C20 N4 115.08(16)
N4 C22 C21 115.52(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni1 N1 1.8750(16)
Ni1 N2 1.9418(16)
Ni1 S1 2.1386(6)
Ni1 S2 2.2173(6)
S1 C1 1.838(2)
S2 C9 1.7730(19)
N1 C3 1.325(2)
N1 C2 1.461(2)
N2 C8 1.341(2)
N2 C4 1.356(2)
N3 C14 1.392(2)
O1 C3 1.252(2)
C1 C2 1.517(3)
C3 C4 1.504(3)
C4 C5 1.387(3)
C5 C6 1.388(3)
C6 C7 1.389(3)
C7 C8 1.390(3)
C9 C10 1.405(3)
C9 C14 1.413(3)
C10 C11 1.388(3)
C11 C12 1.388(3)
C12 C13 1.387(3)
C13 C14 1.401(3)
N4 C16 1.515(2)
N4 C22 1.520(3)
N4 C20 1.520(2)
N4 C18 1.521(2)
C15 C16 1.514(3)
C17 C18 1.514(3)
C19 C20 1.519(3)
C21 C22 1.520(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O1 0.88 2.29 3.050(2) 144.9 4_575
C13 H13A O1 0.95 2.35 3.147(2) 140.6 4_575
