#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/90/4329075.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_4329075
loop_
_publ_author_name
'Jun-ichi Nishigaki'
'Tsuyoshi Matsumoto'
'Kazuyuki Tatsumi'
_publ_section_title
;
 Model Studies of Methyl CoM Reductase: Methane Formation via CH3-S Bond
 Cleavage of Ni(I) Tetraazacyclic Complexes Having Intramolecular Methyl
 Sulfide Pendants
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5173
_journal_page_last               5187
_journal_paper_doi               10.1021/ic300017k
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C16 H35 N4 Ni S2, C F3 O3 S, 0.5(C6 H5 F) '
_chemical_formula_sum            'C20 H37.5 F3.5 N4 Ni O3 S3'
_chemical_formula_weight         603.42
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                113.522(7)
_cell_angle_beta                 101.034(8)
_cell_angle_gamma                98.780(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6154(14)
_cell_length_b                   12.5521(15)
_cell_length_c                   14.1876(17)
_cell_measurement_reflns_used    4172
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1335.3(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16349
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_exptl_absorpt_coefficient_mu    1.015
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       block
_exptl_crystal_F_000             634.00
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     317
_refine_ls_number_reflns         6081
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0400P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0806
_reflns_number_gt                5009
_reflns_number_total             6081
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ic300017k_si_002_13.cif
_cod_data_source_block           RRSS-[Ni(mtc-H)]OTf_Complex18
_cod_original_formula_sum        'C20 H37.50 F3.50 N4 Ni O3 S3 '
_cod_database_code               4329075
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-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
Ni(1) Ni 0.09291(3) 0.366313(19) 0.191566(17) 0.01682(6) Uani 1.00 1 d .
S(1) S 0.74973(6) 0.54460(5) 0.30568(4) 0.02865(12) Uani 1.00 1 d .
S(2) S -0.56518(6) 0.18677(5) 0.01448(4) 0.03121(12) Uani 1.00 1 d .
S(3) S 0.44877(6) 0.15619(4) 0.31293(4) 0.02607(11) Uani 1.00 1 d .
F(1) F 0.21952(19) 0.04051(16) 0.35754(14) 0.0671(4) Uani 1.00 1 d .
F(2) F 0.4083(2) -0.04920(13) 0.32430(13) 0.0635(4) Uani 1.00 1 d .
F(3) F 0.4539(2) 0.10459(14) 0.47435(11) 0.0619(4) Uani 1.00 1 d .
F(4) F 0.2062(8) 0.1612(4) 0.6736(3) 0.170(3) Uani 0.50 1 d P
O(1) O 0.3500(2) 0.09531(16) 0.20407(12) 0.0469(4) Uani 1.00 1 d .
O(2) O 0.40983(18) 0.26583(13) 0.37609(12) 0.0352(3) Uani 1.00 1 d .
O(3) O 0.62006(18) 0.16383(16) 0.32984(15) 0.0470(4) Uani 1.00 1 d .
N(1) N 0.25723(17) 0.52093(13) 0.27864(12) 0.0206(3) Uani 1.00 1 d .
N(2) N 0.10287(17) 0.32524(13) 0.31239(11) 0.0201(3) Uani 1.00 1 d .
N(3) N -0.06998(17) 0.21140(13) 0.10520(11) 0.0186(3) Uani 1.00 1 d .
N(4) N 0.07460(18) 0.40532(14) 0.07607(12) 0.0228(3) Uani 1.00 1 d .
C(1) C 0.2477(2) 0.59135(17) 0.38982(15) 0.0269(4) Uani 1.00 1 d .
C(2) C 0.2567(2) 0.52516(18) 0.45808(15) 0.0285(4) Uani 1.00 1 d .
C(3) C 0.1103(2) 0.41930(18) 0.41845(14) 0.0275(4) Uani 1.00 1 d .
C(4) C -0.0316(2) 0.21820(17) 0.28197(15) 0.0252(4) Uani 1.00 1 d .
C(5) C -0.0537(2) 0.13840(16) 0.16627(15) 0.0248(4) Uani 1.00 1 d .
C(6) C -0.0496(2) 0.13906(17) -0.00228(15) 0.0256(4) Uani 1.00 1 d .
C(7) C -0.0588(2) 0.20122(19) -0.07415(15) 0.0306(4) Uani 1.00 1 d .
C(8) C 0.0726(2) 0.31618(19) -0.02891(15) 0.0276(4) Uani 1.00 1 d .
C(9) C 0.1982(2) 0.51415(18) 0.10232(16) 0.0278(4) Uani 1.00 1 d .
C(10) C 0.2280(2) 0.59424(17) 0.21895(17) 0.0297(4) Uani 1.00 1 d .
C(11) C 0.4183(2) 0.48882(16) 0.27832(14) 0.0203(3) Uani 1.00 1 d .
C(12) C 0.5711(2) 0.59356(17) 0.33711(15) 0.0253(3) Uani 1.00 1 d .
C(13) C 0.7202(2) 0.5349(2) 0.17343(18) 0.0375(5) Uani 1.00 1 d .
C(14) C -0.2304(2) 0.24457(16) 0.09726(14) 0.0209(3) Uani 1.00 1 d .
C(15) C -0.3832(2) 0.13930(17) 0.04797(17) 0.0278(4) Uani 1.00 1 d .
C(16) C -0.5490(3) 0.1893(3) -0.1089(2) 0.0571(7) Uani 1.00 1 d .
C(17) C 0.3799(2) 0.0587(2) 0.37056(18) 0.0380(5) Uani 1.00 1 d .
C(18) C 0.1054(4) 0.0835(3) 0.5906(2) 0.0803(10) Uani 1.00 1 d .
C(19) C 0.1184(3) -0.0299(3) 0.5560(3) 0.0697(9) Uani 1.00 1 d .
C(20) C 0.0118(5) -0.1157(3) 0.4636(3) 0.0765(10) Uani 1.00 1 d .
H(1) H 0.1990 0.3009 0.3219 0.024 Uiso 1.00 1 c R
H(2) H 0.1437 0.6160 0.3855 0.032 Uiso 1.00 1 c R
H(3) H 0.3382 0.6654 0.4256 0.032 Uiso 1.00 1 c R
H(4) H 0.2645 0.5816 0.5324 0.034 Uiso 1.00 1 c R
H(5) H 0.3573 0.4961 0.4592 0.034 Uiso 1.00 1 c R
H(6) H 0.1168 0.3848 0.4704 0.033 Uiso 1.00 1 c R
H(7) H 0.0090 0.4473 0.4137 0.033 Uiso 1.00 1 c R
H(8) H -0.1336 0.2422 0.2925 0.030 Uiso 1.00 1 c R
H(9) H -0.0027 0.1760 0.3261 0.030 Uiso 1.00 1 c R
H(10) H 0.0417 0.1040 0.1580 0.030 Uiso 1.00 1 c R
H(11) H -0.1529 0.0714 0.1384 0.030 Uiso 1.00 1 c R
H(12) H -0.1355 0.0624 -0.0382 0.031 Uiso 1.00 1 c R
H(13) H 0.0576 0.1195 0.0075 0.031 Uiso 1.00 1 c R
H(14) H -0.0493 0.1462 -0.1446 0.037 Uiso 1.00 1 c R
H(15) H -0.1671 0.2190 -0.0857 0.037 Uiso 1.00 1 c R
H(16) H 0.1801 0.2968 -0.0239 0.033 Uiso 1.00 1 c R
H(17) H 0.0587 0.3523 -0.0796 0.033 Uiso 1.00 1 c R
H(18) H 0.1587 0.5547 0.0588 0.033 Uiso 1.00 1 c R
H(19) H 0.3005 0.4940 0.0877 0.033 Uiso 1.00 1 c R
H(20) H 0.3245 0.6626 0.2439 0.036 Uiso 1.00 1 c R
H(21) H 0.1320 0.6264 0.2313 0.036 Uiso 1.00 1 c R
H(22) H 0.4197 0.4456 0.2030 0.024 Uiso 1.00 1 c R
H(23) H 0.4249 0.4323 0.3107 0.024 Uiso 1.00 1 c R
H(24) H 0.5862 0.6261 0.4153 0.030 Uiso 1.00 1 c R
H(25) H 0.5574 0.6585 0.3159 0.030 Uiso 1.00 1 c R
H(26) H 0.8206 0.5263 0.1516 0.045 Uiso 1.00 1 c R
H(27) H 0.6937 0.6080 0.1733 0.045 Uiso 1.00 1 c R
H(28) H 0.6302 0.4649 0.1233 0.045 Uiso 1.00 1 c R
H(29) H -0.2366 0.2900 0.0541 0.025 Uiso 1.00 1 c R
H(30) H -0.2323 0.2991 0.1700 0.025 Uiso 1.00 1 c R
H(31) H -0.3937 0.1055 0.0994 0.033 Uiso 1.00 1 c R
H(32) H -0.3717 0.0754 -0.0174 0.033 Uiso 1.00 1 c R
H(33) H -0.5014 0.1244 -0.1471 0.069 Uiso 1.00 1 c R
H(34) H -0.4787 0.2668 -0.0936 0.069 Uiso 1.00 1 c R
H(35) H -0.6579 0.1782 -0.1532 0.069 Uiso 1.00 1 c R
H(36) H 0.2012 -0.0499 0.5957 0.084 Uiso 1.00 1 c R
H(37) H 0.0219 -0.1964 0.4387 0.104 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Ni Ni 0.339 1.112
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.017 0.010
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N(1) Ni(1) N(2) 93.46(6) yes . .
N(1) Ni(1) N(3) 179.54(7) yes . .
N(1) Ni(1) N(4) 87.63(6) yes . .
N(2) Ni(1) N(3) 86.21(6) yes . .
N(2) Ni(1) N(4) 177.71(6) yes . .
N(3) Ni(1) N(4) 92.71(6) yes . .
C(12) S(1) C(13) 100.18(11) yes . .
C(15) S(2) C(16) 99.52(13) yes . .
O(1) S(3) O(2) 114.08(10) yes . .
O(1) S(3) O(3) 116.28(11) yes . .
O(1) S(3) C(17) 103.34(10) yes . .
O(2) S(3) O(3) 114.53(8) yes . .
O(2) S(3) C(17) 102.10(11) yes . .
O(3) S(3) C(17) 104.07(12) yes . .
Ni(1) N(1) C(1) 116.55(12) yes . .
Ni(1) N(1) C(10) 104.76(9) yes . .
Ni(1) N(1) C(11) 104.24(9) yes . .
C(1) N(1) C(10) 107.54(15) yes . .
C(1) N(1) C(11) 111.78(13) yes . .
C(10) N(1) C(11) 111.83(16) yes . .
Ni(1) N(2) C(3) 119.26(14) yes . .
Ni(1) N(2) C(4) 109.96(11) yes . .
C(3) N(2) C(4) 109.68(15) yes . .
Ni(1) N(3) C(5) 106.99(8) yes . .
Ni(1) N(3) C(6) 115.23(12) yes . .
Ni(1) N(3) C(14) 103.92(10) yes . .
C(5) N(3) C(6) 107.00(15) yes . .
C(5) N(3) C(14) 111.66(15) yes . .
C(6) N(3) C(14) 112.01(13) yes . .
Ni(1) N(4) C(8) 120.30(15) yes . .
Ni(1) N(4) C(9) 111.62(11) yes . .
C(8) N(4) C(9) 107.28(17) yes . .
N(1) C(1) C(2) 114.65(16) yes . .
C(1) C(2) C(3) 112.87(15) yes . .
N(2) C(3) C(2) 111.56(17) yes . .
N(2) C(4) C(5) 106.35(17) yes . .
N(3) C(5) C(4) 108.60(15) yes . .
N(3) C(6) C(7) 114.02(17) yes . .
C(6) C(7) C(8) 112.88(15) yes . .
N(4) C(8) C(7) 114.93(18) yes . .
N(4) C(9) C(10) 106.97(19) yes . .
N(1) C(10) C(9) 107.79(16) yes . .
N(1) C(11) C(12) 116.14(15) yes . .
S(1) C(12) C(11) 110.44(12) yes . .
N(3) C(14) C(15) 115.70(15) yes . .
S(2) C(15) C(14) 111.14(15) yes . .
S(3) C(17) F(1) 110.6(2) yes . .
S(3) C(17) F(2) 112.08(19) yes . .
S(3) C(17) F(3) 111.78(15) yes . .
F(1) C(17) F(2) 106.67(17) yes . .
F(1) C(17) F(3) 108.2(2) yes . .
F(2) C(17) F(3) 107.2(2) yes . .
F(4) C(18) C(19) 118.2(4) yes . .
F(4) C(18) C(20) 119.5(4) yes . 2_556
C(19) C(18) C(20) 122.3(2) yes . 2_556
C(18) C(19) C(20) 119.0(3) yes . .
C(18) C(20) C(19) 118.7(3) yes 2_556 .
Ni(1) N(2) H(1) 105.6 no . .
C(3) N(2) H(1) 105.7 no . .
C(4) N(2) H(1) 105.7 no . .
N(1) C(1) H(2) 108.6 no . .
N(1) C(1) H(3) 108.6 no . .
C(2) C(1) H(2) 108.6 no . .
C(2) C(1) H(3) 108.6 no . .
H(2) C(1) H(3) 107.6 no . .
C(1) C(2) H(4) 109.0 no . .
C(1) C(2) H(5) 109.0 no . .
C(3) C(2) H(4) 109.0 no . .
C(3) C(2) H(5) 109.0 no . .
H(4) C(2) H(5) 107.8 no . .
N(2) C(3) H(6) 109.3 no . .
N(2) C(3) H(7) 109.3 no . .
C(2) C(3) H(6) 109.3 no . .
C(2) C(3) H(7) 109.3 no . .
H(6) C(3) H(7) 108.0 no . .
N(2) C(4) H(8) 110.5 no . .
N(2) C(4) H(9) 110.5 no . .
C(5) C(4) H(8) 110.5 no . .
C(5) C(4) H(9) 110.5 no . .
H(8) C(4) H(9) 108.7 no . .
N(3) C(5) H(10) 110.0 no . .
N(3) C(5) H(11) 110.0 no . .
C(4) C(5) H(10) 110.0 no . .
C(4) C(5) H(11) 110.0 no . .
H(10) C(5) H(11) 108.4 no . .
N(3) C(6) H(12) 108.7 no . .
N(3) C(6) H(13) 108.8 no . .
C(7) C(6) H(12) 108.7 no . .
C(7) C(6) H(13) 108.7 no . .
H(12) C(6) H(13) 107.7 no . .
C(6) C(7) H(14) 109.0 no . .
C(6) C(7) H(15) 109.0 no . .
C(8) C(7) H(14) 109.0 no . .
C(8) C(7) H(15) 109.0 no . .
H(14) C(7) H(15) 107.8 no . .
N(4) C(8) H(16) 108.5 no . .
N(4) C(8) H(17) 108.5 no . .
C(7) C(8) H(16) 108.5 no . .
C(7) C(8) H(17) 108.5 no . .
H(16) C(8) H(17) 107.5 no . .
N(4) C(9) H(18) 110.3 no . .
N(4) C(9) H(19) 110.3 no . .
C(10) C(9) H(18) 110.3 no . .
C(10) C(9) H(19) 110.3 no . .
H(18) C(9) H(19) 108.6 no . .
N(1) C(10) H(20) 110.1 no . .
N(1) C(10) H(21) 110.1 no . .
C(9) C(10) H(20) 110.2 no . .
C(9) C(10) H(21) 110.2 no . .
H(20) C(10) H(21) 108.5 no . .
N(1) C(11) H(22) 108.3 no . .
N(1) C(11) H(23) 108.2 no . .
C(12) C(11) H(22) 108.2 no . .
C(12) C(11) H(23) 108.2 no . .
H(22) C(11) H(23) 107.4 no . .
S(1) C(12) H(24) 109.6 no . .
S(1) C(12) H(25) 109.6 no . .
C(11) C(12) H(24) 109.6 no . .
C(11) C(12) H(25) 109.6 no . .
H(24) C(12) H(25) 108.1 no . .
S(1) C(13) H(26) 109.5 no . .
S(1) C(13) H(27) 109.5 no . .
S(1) C(13) H(28) 109.5 no . .
H(26) C(13) H(27) 109.5 no . .
H(26) C(13) H(28) 109.5 no . .
H(27) C(13) H(28) 109.5 no . .
N(3) C(14) H(29) 108.4 no . .
N(3) C(14) H(30) 108.4 no . .
C(15) C(14) H(29) 108.4 no . .
C(15) C(14) H(30) 108.4 no . .
H(29) C(14) H(30) 107.4 no . .
S(2) C(15) H(31) 109.4 no . .
S(2) C(15) H(32) 109.4 no . .
C(14) C(15) H(31) 109.4 no . .
C(14) C(15) H(32) 109.4 no . .
H(31) C(15) H(32) 108.0 no . .
S(2) C(16) H(33) 109.5 no . .
S(2) C(16) H(34) 109.5 no . .
S(2) C(16) H(35) 109.5 no . .
H(33) C(16) H(34) 109.5 no . .
H(33) C(16) H(35) 109.5 no . .
H(34) C(16) H(35) 109.5 no . .
C(18) C(19) H(36) 120.5 no . .
C(20) C(19) H(36) 120.5 no . .
C(18) C(20) H(37) 122.4 no 2_556 .
C(19) C(20) H(37) 118.8 no . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
Ni(1) N(1) 1.9685(12) yes .
Ni(1) N(2) 1.9683(18) yes .
Ni(1) N(3) 1.9644(12) yes .
Ni(1) N(4) 1.8748(19) yes .
S(1) C(12) 1.810(2) yes .
S(1) C(13) 1.796(2) yes .
S(2) C(15) 1.807(2) yes .
S(2) C(16) 1.794(3) yes .
S(3) O(1) 1.4316(14) yes .
S(3) O(2) 1.4426(15) yes .
S(3) O(3) 1.4309(16) yes .
S(3) C(17) 1.811(3) yes .
F(1) C(17) 1.330(2) yes .
F(2) C(17) 1.333(2) yes .
F(3) C(17) 1.326(2) yes .
F(4) C(18) 1.235(5) yes .
N(1) C(1) 1.495(2) yes .
N(1) C(10) 1.496(3) yes .
N(1) C(11) 1.503(2) yes .
N(2) C(3) 1.478(2) yes .
N(2) C(4) 1.485(2) yes .
N(3) C(5) 1.495(3) yes .
N(3) C(6) 1.492(2) yes .
N(3) C(14) 1.500(2) yes .
N(4) C(8) 1.458(2) yes .
N(4) C(9) 1.462(2) yes .
C(1) C(2) 1.506(3) yes .
C(2) C(3) 1.514(2) yes .
C(4) C(5) 1.498(2) yes .
C(6) C(7) 1.509(3) yes .
C(7) C(8) 1.503(2) yes .
C(9) C(10) 1.498(2) yes .
C(11) C(12) 1.527(2) yes .
C(14) C(15) 1.532(2) yes .
C(18) C(19) 1.339(6) yes .
C(18) C(20) 1.360(6) yes 2_556
C(19) C(20) 1.353(4) yes .
N(2) H(1) 0.930 no .
C(1) H(2) 0.990 no .
C(1) H(3) 0.990 no .
C(2) H(4) 0.990 no .
C(2) H(5) 0.990 no .
C(3) H(6) 0.990 no .
C(3) H(7) 0.990 no .
C(4) H(8) 0.990 no .
C(4) H(9) 0.990 no .
C(5) H(10) 0.990 no .
C(5) H(11) 0.990 no .
C(6) H(12) 0.990 no .
C(6) H(13) 0.990 no .
C(7) H(14) 0.990 no .
C(7) H(15) 0.990 no .
C(8) H(16) 0.990 no .
C(8) H(17) 0.990 no .
C(9) H(18) 0.990 no .
C(9) H(19) 0.990 no .
C(10) H(20) 0.990 no .
C(10) H(21) 0.990 no .
C(11) H(22) 0.990 no .
C(11) H(23) 0.990 no .
C(12) H(24) 0.990 no .
C(12) H(25) 0.990 no .
C(13) H(26) 0.980 no .
C(13) H(27) 0.980 no .
C(13) H(28) 0.980 no .
C(14) H(29) 0.990 no .
C(14) H(30) 0.990 no .
C(15) H(31) 0.990 no .
C(15) H(32) 0.990 no .
C(16) H(33) 0.980 no .
C(16) H(34) 0.980 no .
C(16) H(35) 0.980 no .
C(19) H(36) 0.950 no .
C(20) H(37) 0.955 no .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
S(1) F(4) 3.540(5) 2_666
S(2) O(1) 3.471(2) 1_455
F(1) C(18) 3.490(4) .
F(1) C(18) 3.342(4) 2_556
F(1) C(19) 3.487(5) .
F(1) C(19) 3.373(4) 2_556
F(1) C(20) 3.409(5) .
F(1) C(20) 3.450(5) 2_556
F(2) F(3) 3.255(2) 2_656
F(2) C(16) 3.418(3) 2_555
F(3) F(2) 3.255(2) 2_656
F(3) F(3) 3.162(2) 2_656
F(4) S(1) 3.540(5) 2_666
F(4) C(12) 3.444(6) 2_666
F(4) C(13) 3.434(5) 2_666
F(4) C(16) 3.242(6) 1_656
O(1) S(2) 3.471(2) 1_655
O(1) C(5) 3.574(2) .
O(1) C(6) 3.4157(19) 2_555
O(2) N(2) 2.931(2) .
O(2) C(1) 3.582(2) 2_666
O(2) C(2) 3.545(2) .
O(2) C(2) 3.2949(19) 2_666
O(2) C(3) 3.452(2) .
O(2) C(11) 3.583(3) .
O(3) C(4) 3.234(2) 1_655
O(3) C(19) 3.529(5) 2_656
N(2) O(2) 2.931(2) .
C(1) O(2) 3.582(2) 2_666
C(2) O(2) 3.545(2) .
C(2) O(2) 3.2949(19) 2_666
C(3) O(2) 3.452(2) .
C(3) C(3) 3.491(2) 2_566
C(4) O(3) 3.234(2) 1_455
C(5) O(1) 3.574(2) .
C(6) O(1) 3.4157(19) 2_555
C(11) O(2) 3.583(3) .
C(12) F(4) 3.444(6) 2_666
C(13) F(4) 3.434(5) 2_666
C(13) C(14) 3.483(3) 1_655
C(14) C(13) 3.483(3) 1_455
C(15) C(15) 3.337(2) 2_455
C(16) F(2) 3.418(3) 2_555
C(16) F(4) 3.242(6) 1_454
C(18) F(1) 3.490(4) .
C(18) F(1) 3.342(4) 2_556
C(19) F(1) 3.487(5) .
C(19) F(1) 3.373(4) 2_556
C(19) O(3) 3.529(5) 2_656
C(20) F(1) 3.409(5) .
C(20) F(1) 3.450(5) 2_556
Ni(1) H(26) 3.420 1_455
S(1) H(2) 3.224 1_655
S(1) H(4) 3.279 2_666
S(1) H(6) 2.871 2_666
S(1) H(7) 3.138 1_655
S(1) H(30) 2.958 1_655
S(1) H(37) 3.273 1_665
S(2) H(11) 3.328 2_455
S(2) H(13) 3.203 1_455
S(2) H(16) 2.843 1_455
S(2) H(22) 3.325 1_455
S(2) H(28) 3.212 1_455
S(2) H(31) 3.294 2_455
S(2) H(32) 3.271 2_455
S(3) H(1) 3.010 .
S(3) H(3) 3.414 2_666
S(3) H(4) 3.381 2_666
S(3) H(10) 3.572 .
S(3) H(23) 3.516 .
S(3) H(31) 3.424 1_655
S(3) H(33) 3.525 2_555
F(1) H(1) 3.525 .
F(1) H(9) 2.834 .
F(1) H(10) 3.393 .
F(1) H(14) 2.894 2_555
F(2) H(14) 3.301 2_555
F(2) H(15) 3.243 2_555
F(2) H(20) 3.240 1_545
F(2) H(33) 2.639 2_555
F(2) H(34) 3.560 2_555
F(2) H(36) 3.208 2_656
F(3) H(3) 2.781 2_666
F(3) H(24) 3.215 2_666
F(3) H(25) 3.294 2_666
F(3) H(36) 3.391 2_656
F(4) H(25) 2.739 2_666
F(4) H(27) 2.712 2_666
F(4) H(33) 3.445 1_656
F(4) H(34) 3.466 1_656
F(4) H(35) 2.420 1_656
O(1) H(1) 3.092 .
O(1) H(10) 2.642 .
O(1) H(12) 2.524 2_555
O(1) H(13) 3.527 .
O(1) H(14) 3.367 2_555
O(1) H(15) 3.559 2_555
O(1) H(31) 2.901 1_655
O(1) H(32) 2.724 2_555
O(1) H(33) 3.112 2_555
O(2) H(1) 2.016 .
O(2) H(3) 2.920 2_666
O(2) H(4) 2.865 2_666
O(2) H(5) 2.799 .
O(2) H(5) 3.036 2_666
O(2) H(6) 3.353 .
O(2) H(9) 3.403 .
O(2) H(23) 2.599 .
O(2) H(24) 2.710 2_666
O(3) H(3) 3.180 2_666
O(3) H(4) 2.885 2_666
O(3) H(8) 2.442 1_655
O(3) H(9) 3.242 1_655
O(3) H(11) 3.572 1_655
O(3) H(31) 3.026 1_655
O(3) H(33) 3.351 2_555
O(3) H(36) 2.605 2_656
N(4) H(17) 3.398 2_565
N(4) H(18) 2.748 2_565
N(4) H(26) 2.976 1_455
C(1) H(37) 3.462 1_565
C(2) H(5) 3.396 2_666
C(2) H(7) 3.163 2_566
C(2) H(24) 3.353 2_666
C(3) H(4) 3.431 2_566
C(3) H(6) 3.452 2_566
C(3) H(7) 2.795 2_566
C(3) H(24) 3.449 2_666
C(4) H(36) 3.544 2_556
C(5) H(12) 3.324 2_555
C(5) H(13) 3.181 2_555
C(6) H(10) 2.989 2_555
C(6) H(11) 3.518 2_555
C(6) H(12) 3.363 2_555
C(6) H(13) 3.206 2_555
C(7) H(10) 3.567 2_555
C(7) H(18) 3.243 2_565
C(8) H(18) 2.826 2_565
C(8) H(21) 3.460 2_565
C(8) H(26) 3.254 2_665
C(8) H(27) 3.421 2_665
C(8) H(35) 3.444 1_655
C(9) H(15) 3.497 2_565
C(9) H(17) 3.017 2_565
C(9) H(18) 3.217 2_565
C(9) H(26) 3.468 1_455
C(9) H(26) 3.399 2_665
C(9) H(34) 3.431 2_565
C(10) H(15) 3.589 2_565
C(10) H(17) 3.187 2_565
C(10) H(26) 3.333 1_455
C(12) H(5) 3.482 2_666
C(12) H(6) 3.337 2_666
C(13) H(17) 3.010 2_665
C(13) H(18) 3.453 2_665
C(13) H(19) 3.542 2_665
C(13) H(21) 3.386 1_655
C(13) H(29) 2.981 1_655
C(13) H(30) 3.032 1_655
C(14) H(26) 3.242 1_455
C(14) H(28) 3.098 1_455
C(15) H(31) 3.006 2_455
C(15) H(32) 2.981 2_455
C(16) H(16) 3.076 1_455
C(16) H(27) 3.354 2_565
C(16) H(28) 3.539 1_455
C(17) H(14) 3.563 2_555
C(17) H(33) 3.552 2_555
C(17) H(36) 3.573 2_656
C(18) H(25) 3.593 2_666
C(18) H(35) 3.428 1_656
C(19) H(9) 3.111 2_556
C(20) H(2) 3.541 1_545
C(20) H(9) 3.370 2_556
H(1) S(3) 3.010 .
H(1) F(1) 3.525 .
H(1) O(1) 3.092 .
H(1) O(2) 2.016 .
H(1) H(24) 3.505 2_666
H(2) S(1) 3.224 1_455
H(2) C(20) 3.541 1_565
H(2) H(6) 3.313 2_566
H(2) H(26) 3.543 1_455
H(2) H(37) 2.618 1_565
H(3) S(3) 3.414 2_666
H(3) F(3) 2.781 2_666
H(3) O(2) 2.920 2_666
H(3) O(3) 3.180 2_666
H(3) H(37) 3.442 1_565
H(4) S(1) 3.279 2_666
H(4) S(3) 3.381 2_666
H(4) O(2) 2.865 2_666
H(4) O(3) 2.885 2_666
H(4) C(3) 3.431 2_566
H(4) H(5) 3.535 2_666
H(4) H(6) 3.370 2_566
H(4) H(7) 2.630 2_566
H(4) H(8) 3.128 2_566
H(4) H(23) 3.213 2_666
H(4) H(24) 3.347 2_666
H(5) O(2) 2.799 .
H(5) O(2) 3.036 2_666
H(5) C(2) 3.396 2_666
H(5) C(12) 3.482 2_666
H(5) H(4) 3.535 2_666
H(5) H(5) 2.478 2_666
H(5) H(23) 3.128 2_666
H(5) H(24) 2.800 2_666
H(6) S(1) 2.871 2_666
H(6) O(2) 3.353 .
H(6) C(3) 3.452 2_566
H(6) C(12) 3.337 2_666
H(6) H(2) 3.313 2_566
H(6) H(4) 3.370 2_566
H(6) H(7) 2.633 2_566
H(6) H(24) 2.810 2_666
H(6) H(37) 3.293 2_556
H(7) S(1) 3.138 1_455
H(7) C(2) 3.163 2_566
H(7) C(3) 2.795 2_566
H(7) H(4) 2.630 2_566
H(7) H(6) 2.633 2_566
H(7) H(7) 2.323 2_566
H(8) O(3) 2.442 1_455
H(8) H(4) 3.128 2_566
H(8) H(36) 3.415 2_556
H(9) F(1) 2.834 .
H(9) O(2) 3.403 .
H(9) O(3) 3.242 1_455
H(9) C(19) 3.111 2_556
H(9) C(20) 3.370 2_556
H(9) H(36) 2.821 2_556
H(9) H(37) 3.281 2_556
H(10) S(3) 3.572 .
H(10) F(1) 3.393 .
H(10) O(1) 2.642 .
H(10) C(6) 2.989 2_555
H(10) C(7) 3.567 2_555
H(10) H(12) 2.473 2_555
H(10) H(13) 2.712 2_555
H(10) H(14) 3.082 2_555
H(11) S(2) 3.328 2_455
H(11) O(3) 3.572 1_455
H(11) C(6) 3.518 2_555
H(11) H(12) 3.426 2_555
H(11) H(13) 2.827 2_555
H(11) H(14) 3.477 2_555
H(11) H(35) 3.408 2_455
H(12) O(1) 2.524 2_555
H(12) C(5) 3.324 2_555
H(12) C(6) 3.363 2_555
H(12) H(10) 2.473 2_555
H(12) H(11) 3.426 2_555
H(12) H(12) 3.254 2_555
H(12) H(13) 2.647 2_555
H(13) S(2) 3.203 1_655
H(13) O(1) 3.527 .
H(13) C(5) 3.181 2_555
H(13) C(6) 3.206 2_555
H(13) H(10) 2.712 2_555
H(13) H(11) 2.827 2_555
H(13) H(12) 2.647 2_555
H(13) H(13) 2.920 2_555
H(14) F(1) 2.894 2_555
H(14) F(2) 3.301 2_555
H(14) O(1) 3.367 2_555
H(14) C(17) 3.563 2_555
H(14) H(10) 3.082 2_555
H(14) H(11) 3.477 2_555
H(14) H(35) 3.366 1_655
H(15) F(2) 3.243 2_555
H(15) O(1) 3.559 2_555
H(15) C(9) 3.497 2_565
H(15) C(10) 3.589 2_565
H(15) H(18) 2.698 2_565
H(15) H(20) 3.346 2_565
H(15) H(21) 3.374 2_565
H(16) S(2) 2.843 1_655
H(16) C(16) 3.076 1_655
H(16) H(26) 3.381 2_665
H(16) H(27) 3.101 2_665
H(16) H(34) 3.304 1_655
H(16) H(35) 2.639 1_655
H(17) N(4) 3.398 2_565
H(17) C(9) 3.017 2_565
H(17) C(10) 3.187 2_565
H(17) C(13) 3.010 2_665
H(17) H(18) 2.358 2_565
H(17) H(20) 3.589 2_565
H(17) H(21) 2.577 2_565
H(17) H(26) 2.369 2_665
H(17) H(27) 2.803 2_665
H(17) H(28) 3.567 2_665
H(17) H(35) 3.551 1_655
H(18) N(4) 2.748 2_565
H(18) C(7) 3.243 2_565
H(18) C(8) 2.826 2_565
H(18) C(9) 3.217 2_565
H(18) C(13) 3.453 2_665
H(18) H(15) 2.698 2_565
H(18) H(17) 2.358 2_565
H(18) H(18) 2.725 2_565
H(18) H(26) 3.445 1_455
H(18) H(26) 2.795 2_665
H(18) H(28) 3.386 2_665
H(18) H(29) 3.052 2_565
H(18) H(34) 3.094 2_565
H(19) C(13) 3.542 2_665
H(19) H(26) 3.248 2_665
H(19) H(27) 3.414 2_665
H(19) H(28) 3.377 2_665
H(19) H(34) 3.119 2_565
H(20) F(2) 3.240 1_565
H(20) H(15) 3.346 2_565
H(20) H(17) 3.589 2_565
H(20) H(34) 3.054 2_565
H(21) C(8) 3.460 2_565
H(21) C(13) 3.386 1_455
H(21) H(15) 3.374 2_565
H(21) H(17) 2.577 2_565
H(21) H(26) 2.594 1_455
H(21) H(37) 3.315 1_565
H(22) S(2) 3.325 1_655
H(23) S(3) 3.516 .
H(23) O(2) 2.599 .
H(23) H(4) 3.213 2_666
H(23) H(5) 3.128 2_666
H(24) F(3) 3.215 2_666
H(24) O(2) 2.710 2_666
H(24) C(2) 3.353 2_666
H(24) C(3) 3.449 2_666
H(24) H(1) 3.505 2_666
H(24) H(4) 3.347 2_666
H(24) H(5) 2.800 2_666
H(24) H(6) 2.810 2_666
H(25) F(3) 3.294 2_666
H(25) F(4) 2.739 2_666
H(25) C(18) 3.593 2_666
H(26) Ni(1) 3.420 1_655
H(26) N(4) 2.976 1_655
H(26) C(8) 3.254 2_665
H(26) C(9) 3.468 1_655
H(26) C(9) 3.399 2_665
H(26) C(10) 3.333 1_655
H(26) C(14) 3.242 1_655
H(26) H(2) 3.543 1_655
H(26) H(16) 3.381 2_665
H(26) H(17) 2.369 2_665
H(26) H(18) 3.445 1_655
H(26) H(18) 2.795 2_665
H(26) H(19) 3.248 2_665
H(26) H(21) 2.594 1_655
H(26) H(29) 2.640 1_655
H(26) H(30) 2.942 1_655
H(27) F(4) 2.712 2_666
H(27) C(8) 3.421 2_665
H(27) C(16) 3.354 2_565
H(27) H(16) 3.101 2_665
H(27) H(17) 2.803 2_665
H(27) H(19) 3.414 2_665
H(27) H(34) 2.947 2_565
H(27) H(35) 2.865 2_565
H(28) S(2) 3.212 1_655
H(28) C(14) 3.098 1_655
H(28) C(16) 3.539 1_655
H(28) H(17) 3.567 2_665
H(28) H(18) 3.386 2_665
H(28) H(19) 3.377 2_665
H(28) H(29) 2.565 1_655
H(28) H(30) 2.781 1_655
H(28) H(34) 2.934 1_655
H(29) C(13) 2.981 1_455
H(29) H(18) 3.052 2_565
H(29) H(26) 2.640 1_455
H(29) H(28) 2.565 1_455
H(30) S(1) 2.958 1_455
H(30) C(13) 3.032 1_455
H(30) H(26) 2.942 1_455
H(30) H(28) 2.781 1_455
H(31) S(2) 3.294 2_455
H(31) S(3) 3.424 1_455
H(31) O(1) 2.901 1_455
H(31) O(3) 3.026 1_455
H(31) C(15) 3.006 2_455
H(31) H(31) 2.983 2_455
H(31) H(32) 2.487 2_455
H(31) H(33) 3.256 2_455
H(32) S(2) 3.271 2_455
H(32) O(1) 2.724 2_555
H(32) C(15) 2.981 2_455
H(32) H(31) 2.487 2_455
H(32) H(32) 2.932 2_455
H(33) S(3) 3.525 2_555
H(33) F(2) 2.639 2_555
H(33) F(4) 3.445 1_454
H(33) O(1) 3.112 2_555
H(33) O(3) 3.351 2_555
H(33) C(17) 3.552 2_555
H(33) H(31) 3.256 2_455
H(34) F(2) 3.560 2_555
H(34) F(4) 3.466 1_454
H(34) C(9) 3.431 2_565
H(34) H(16) 3.304 1_455
H(34) H(18) 3.094 2_565
H(34) H(19) 3.119 2_565
H(34) H(20) 3.054 2_565
H(34) H(27) 2.947 2_565
H(34) H(28) 2.934 1_455
H(35) F(4) 2.420 1_454
H(35) C(8) 3.444 1_455
H(35) C(18) 3.428 1_454
H(35) H(11) 3.408 2_455
H(35) H(14) 3.366 1_455
H(35) H(16) 2.639 1_455
H(35) H(17) 3.551 1_455
H(35) H(27) 2.865 2_565
H(35) H(36) 3.392 1_454
H(36) F(2) 3.208 2_656
H(36) F(3) 3.391 2_656
H(36) O(3) 2.605 2_656
H(36) C(4) 3.544 2_556
H(36) C(17) 3.573 2_656
H(36) H(8) 3.415 2_556
H(36) H(9) 2.821 2_556
H(36) H(35) 3.392 1_656
H(37) S(1) 3.273 1_445
H(37) C(1) 3.462 1_545
H(37) H(2) 2.618 1_545
H(37) H(3) 3.442 1_545
H(37) H(6) 3.293 2_556
H(37) H(9) 3.281 2_556
H(37) H(21) 3.315 1_545
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_3
_geom_torsion_site_symmetry_4
N(1) Ni(1) N(2) C(3) 42.01(13) . . .
N(1) Ni(1) N(2) C(4) 169.90(12) . . .
N(2) Ni(1) N(1) C(1) -39.65(15) . . .
N(2) Ni(1) N(1) C(10) -158.33(12) . . .
N(2) Ni(1) N(1) C(11) 84.04(13) . . .
N(1) Ni(1) N(4) C(8) 134.54(13) . . .
N(1) Ni(1) N(4) C(9) 7.54(13) . . .
N(4) Ni(1) N(1) C(1) 138.34(15) . . .
N(4) Ni(1) N(1) C(10) 19.65(12) . . .
N(4) Ni(1) N(1) C(11) -97.97(13) . . .
N(2) Ni(1) N(3) C(5) -17.37(12) . . .
N(2) Ni(1) N(3) C(6) -136.18(14) . . .
N(2) Ni(1) N(3) C(14) 100.89(12) . . .
N(3) Ni(1) N(2) C(3) -138.31(13) . . .
N(3) Ni(1) N(2) C(4) -10.42(12) . . .
N(3) Ni(1) N(4) C(8) -45.16(13) . . .
N(3) Ni(1) N(4) C(9) -172.15(13) . . .
N(4) Ni(1) N(3) C(5) 164.65(12) . . .
N(4) Ni(1) N(3) C(6) 45.84(15) . . .
N(4) Ni(1) N(3) C(14) -77.09(13) . . .
C(13) S(1) C(12) C(11) 75.91(17) . . .
C(16) S(2) C(15) C(14) 79.33(17) . . .
O(1) S(3) C(17) F(1) -56.23(17) . . .
O(1) S(3) C(17) F(2) 62.68(17) . . .
O(1) S(3) C(17) F(3) -176.94(18) . . .
O(2) S(3) C(17) F(1) 62.43(15) . . .
O(2) S(3) C(17) F(2) -178.65(14) . . .
O(2) S(3) C(17) F(3) -58.28(19) . . .
O(3) S(3) C(17) F(1) -178.14(14) . . .
O(3) S(3) C(17) F(2) -59.22(16) . . .
O(3) S(3) C(17) F(3) 61.16(19) . . .
Ni(1) N(1) C(1) C(2) 56.70(18) . . .
Ni(1) N(1) C(10) C(9) -42.29(17) . . .
Ni(1) N(1) C(11) C(12) 177.67(15) . . .
C(1) N(1) C(10) C(9) -166.90(15) . . .
C(10) N(1) C(1) C(2) 173.88(14) . . .
C(1) N(1) C(11) C(12) -55.6(2) . . .
C(11) N(1) C(1) C(2) -63.0(2) . . .
C(10) N(1) C(11) C(12) 65.0(2) . . .
C(11) N(1) C(10) C(9) 70.02(16) . . .
Ni(1) N(2) C(3) C(2) -58.0(2) . . .
Ni(1) N(2) C(4) C(5) 35.61(18) . . .
C(3) N(2) C(4) C(5) 168.62(17) . . .
C(4) N(2) C(3) C(2) 174.02(18) . . .
Ni(1) N(3) C(5) C(4) 42.06(16) . . .
Ni(1) N(3) C(6) C(7) -59.88(18) . . .
Ni(1) N(3) C(14) C(15) -171.11(15) . . .
C(5) N(3) C(6) C(7) -178.69(14) . . .
C(6) N(3) C(5) C(4) 166.08(14) . . .
C(5) N(3) C(14) C(15) -56.1(2) . . .
C(14) N(3) C(5) C(4) -71.02(15) . . .
C(6) N(3) C(14) C(15) 63.9(2) . . .
C(14) N(3) C(6) C(7) 58.6(2) . . .
Ni(1) N(4) C(8) C(7) 56.5(2) . . .
Ni(1) N(4) C(9) C(10) -33.1(2) . . .
C(8) N(4) C(9) C(10) -166.88(18) . . .
C(9) N(4) C(8) C(7) -174.56(19) . . .
N(1) C(1) C(2) C(3) -66.2(2) . . .
C(1) C(2) C(3) N(2) 65.1(2) . . .
N(2) C(4) C(5) N(3) -50.98(19) . . .
N(3) C(6) C(7) C(8) 61.3(2) . . .
C(6) C(7) C(8) N(4) -57.8(2) . . .
N(4) C(9) C(10) N(1) 49.7(2) . . .
N(1) C(11) C(12) S(1) -167.88(15) . . .
N(3) C(14) C(15) S(2) -166.65(14) . . .
F(4) C(18) C(19) C(20) -178.1(5) . . .
F(4) C(18) C(20) C(19) 178.1(5) . 2_556 2_556
C(19) C(18) C(20) C(19) -0.3(7) . 2_556 2_556
C(20) C(18) C(19) C(20) 0.3(7) 2_556 . .
C(18) C(19) C(20) C(18) -0.3(6) . . 2_556
