#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:07:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178550 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/57/4065729.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_4065729
loop_
_publ_author_name
'Lee, Way-Zen'
'Tseng, Huan-Sheng'
'Wang, Tzu-Li'
'Tsai, Hui-Lien'
'Kuo, Ting-Shen'
_publ_contact_author             'Way-Zen Lee'
_publ_section_title
;
 Bioinspired Catalytic Conjugate Additions of Thiophenols to α,β-Enones
 by a Disubstituted Benzoate-Bridged Nickel Mimic for the Active Site of
 Urease
;
_journal_issue                   13
_journal_name_full               Organometallics
_journal_page_first              2874
_journal_paper_doi               10.1021/om100103u
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C41 H46 Cl2 N7 Ni2 O13'
_chemical_formula_sum            'C41 H46 Cl2 N7 Ni2 O13'
_chemical_formula_weight         1033.17
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.5660(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.6691(5)
_cell_length_b                   9.5065(2)
_cell_length_c                   18.3372(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     4862.38(17)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack (O & M 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17677
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  0.8705
_exptl_absorpt_correction_T_min  0.6583
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2140
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.069
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1561P)²+1.4979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2044
_refine_ls_wR_factor_ref         0.2175
_reflns_number_gt                3324
_reflns_number_total             4185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100103u_si_002.cif
_cod_data_source_block           737500
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4065729
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_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
C1 C 0.0466(2) 0.5007(6) 0.1539(4) 0.0828(14) Uani 1 1 d . . .
H1 H 0.0188 0.4809 0.1605 0.099 Uiso 1 1 calc R . .
C2 C 0.0454(3) 0.5975(7) 0.0971(5) 0.113(2) Uani 1 1 d . . .
H2 H 0.0170 0.6442 0.0665 0.135 Uiso 1 1 calc R . .
C3 C 0.0855(3) 0.6245(9) 0.0857(5) 0.131(3) Uani 1 1 d . . .
H3 H 0.0846 0.6892 0.0470 0.158 Uiso 1 1 calc R . .
C4 C 0.1277(3) 0.5564(7) 0.1313(4) 0.0970(17) Uani 1 1 d . . .
H4 H 0.1554 0.5728 0.1237 0.116 Uiso 1 1 calc R . .
C5 C 0.1275(2) 0.4613(5) 0.1898(3) 0.0758(13) Uani 1 1 d . . .
C6 C 0.17228(19) 0.3889(5) 0.2452(4) 0.0764(14) Uani 1 1 d . . .
H6A H 0.1919 0.3663 0.2167 0.092 Uiso 1 1 calc R . .
H6B H 0.1906 0.4511 0.2893 0.092 Uiso 1 1 calc R . .
C7 C 0.19857(19) 0.2067(6) 0.3514(4) 0.0778(15) Uani 1 1 d . . .
H7A H 0.2205 0.2834 0.3768 0.093 Uiso 1 1 calc R . .
H7B H 0.2164 0.1334 0.3389 0.093 Uiso 1 1 calc R . .
C8 C 0.1790(2) 0.1493(6) 0.4090(3) 0.0805(13) Uani 1 1 d . . .
C9 C 0.2078(2) 0.0722(6) 0.4769(4) 0.0943(19) Uani 1 1 d . . .
H9 H 0.2391 0.0493 0.4860 0.113 Uiso 1 1 calc R . .
C10 C 0.1895(4) 0.0315(7) 0.5289(4) 0.115(3) Uani 1 1 d . . .
H10 H 0.2085 -0.0176 0.5751 0.138 Uiso 1 1 calc R . .
C11 C 0.1431(3) 0.0624(7) 0.5137(4) 0.102(2) Uani 1 1 d . . .
H11 H 0.1301 0.0344 0.5491 0.122 Uiso 1 1 calc R . .
C12 C 0.1163(2) 0.1343(5) 0.4463(3) 0.0725(13) Uani 1 1 d . . .
H12 H 0.0843 0.1515 0.4348 0.087 Uiso 1 1 calc R . .
C13 C 0.14290(17) 0.1486(5) 0.2119(3) 0.0644(12) Uani 1 1 d . . .
H13A H 0.1703 0.1025 0.2089 0.077 Uiso 1 1 calc R . .
H13B H 0.1250 0.1947 0.1609 0.077 Uiso 1 1 calc R . .
C14 C 0.11143(16) 0.0392(4) 0.2260(3) 0.0601(11) Uani 1 1 d . . .
H14A H 0.0997 -0.0277 0.1822 0.072 Uiso 1 1 calc R . .
H14B H 0.1292 -0.0114 0.2755 0.072 Uiso 1 1 calc R . .
C15 C 0.03696(15) 0.0378(4) 0.2420(2) 0.0516(9) Uani 1 1 d . . .
C16 C 0.0000 0.1124(5) 0.2500 0.0472(12) Uani 1 2 d S . .
C17 C 0.0000 0.2717(6) 0.2500 0.0516(14) Uani 1 2 d S . .
C18 C 0.0366(2) -0.1079(5) 0.2419(4) 0.0809(17) Uani 1 1 d . . .
H18 H 0.0612 -0.1575 0.2364 0.097 Uiso 1 1 calc R . .
C19 C 0.0000 -0.1785(7) 0.2500 0.099(3) Uani 1 2 d S . .
H19 H 0.0000 -0.2763 0.2500 0.119 Uiso 1 2 calc SR . .
Ni1 Ni 0.101163(17) 0.30777(5) 0.29808(3) 0.0479(3) Uani 1 1 d . . .
Cl1 Cl 0.27655(6) 0.27863(16) 0.18757(14) 0.1025(6) Uani 1 1 d . . .
N1 N 0.08762(13) 0.4347(4) 0.1999(2) 0.0613(9) Uani 1 1 d . B .
N2 N 0.16013(13) 0.2570(4) 0.2772(2) 0.0591(9) Uani 1 1 d . B .
N3 N 0.13416(14) 0.1823(4) 0.3948(2) 0.0591(9) Uani 1 1 d . B .
O1 O 0.07170(10) 0.1160(3) 0.23100(17) 0.0527(7) Uani 1 1 d . B .
O2 O 0.03682(11) 0.3347(3) 0.2960(2) 0.0633(8) Uani 1 1 d . B .
O4 O 0.2528(2) 0.1694(5) 0.2009(4) 0.1321(19) Uani 1 1 d . A .
O5 O 0.2488(3) 0.3864(8) 0.1438(5) 0.178(3) Uani 1 1 d . A .
O6 O 0.3220(8) 0.276(3) 0.204(2) 0.250(15) Uani 0.60 1 d P A 1
O6' O 0.2730(10) 0.187(2) 0.1134(17) 0.198(12) Uani 0.40 1 d P A 2
O7 O 0.2954(4) 0.3490(12) 0.2728(7) 0.169(4) Uani 0.65 1 d P A 3
O7' O 0.3158(16) 0.242(4) 0.176(3) 0.19(2) Uani 0.35 1 d P A 4
N4 N 0.1232(8) 0.481(2) 0.3770(15) 0.0613(9) Uani 0.50 1 d P B 5
C24 C 0.1312(6) 0.5873(15) 0.4055(10) 0.0970(17) Uani 0.50 1 d P B 5
C25 C 0.1369(8) 0.7070(14) 0.4507(9) 0.126(7) Uani 0.50 1 d P B 5
H25A H 0.1222 0.6935 0.4874 0.189 Uiso 0.50 1 calc PR B 5
H25B H 0.1220 0.7850 0.4161 0.189 Uiso 0.50 1 calc PR B 5
H25C H 0.1705 0.7259 0.4804 0.189 Uiso 0.50 1 calc PR B 5
O8 O 0.1278(6) 0.4891(15) 0.3666(9) 0.064(3) Uani 0.50 1 d P B 6
C20 C 0.1504(4) 0.5230(13) 0.4395(7) 0.0805(13) Uani 0.50 1 d P B 6
H20A H 0.1833 0.4941 0.4536 0.097 Uiso 0.50 1 calc PR B 6
H20B H 0.1382 0.4608 0.4687 0.097 Uiso 0.50 1 calc PR B 6
C21 C 0.1539(5) 0.6566(13) 0.4755(8) 0.0828(14) Uani 0.50 1 d P B 6
H21A H 0.1474 0.6528 0.5229 0.099 Uiso 0.50 1 calc PR B 6
H21B H 0.1846 0.7012 0.4882 0.099 Uiso 0.50 1 calc PR B 6
C22 C 0.1163(7) 0.7212(18) 0.4098(11) 0.113(2) Uani 0.50 1 d P B 6
H22A H 0.1278 0.8071 0.3952 0.135 Uiso 0.50 1 calc PR B 6
H22B H 0.0902 0.7452 0.4244 0.135 Uiso 0.50 1 calc PR B 6
C23 C 0.0989(4) 0.6215(10) 0.3405(7) 0.0758(13) Uani 0.50 1 d P B 6
H23A H 0.0652 0.6011 0.3244 0.091 Uiso 0.50 1 calc PR B 6
H23B H 0.1028 0.6627 0.2952 0.091 Uiso 0.50 1 calc PR B 6
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'
Cl Cl 0.1484 0.1585 '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 C1 C2 120.7(6) . .
N1 C1 H1 119.7 . .
C2 C1 H1 119.6 . .
C3 C2 C1 120.1(6) . .
C3 C2 H2 119.9 . .
C1 C2 H2 120.0 . .
C4 C3 C2 120.1(6) . .
C4 C3 H3 119.9 . .
C2 C3 H3 120.0 . .
C3 C4 C5 117.8(6) . .
C3 C4 H4 121.1 . .
C5 C4 H4 121.1 . .
N1 C5 C4 121.5(5) . .
N1 C5 C6 117.0(4) . .
C4 C5 C6 121.5(5) . .
N2 C6 C5 110.2(4) . .
N2 C6 H6A 109.6 . .
C5 C6 H6A 109.6 . .
N2 C6 H6B 109.6 . .
C5 C6 H6B 109.6 . .
H6A C6 H6B 108.1 . .
N2 C7 C8 111.5(4) . .
N2 C7 H7A 109.4 . .
C8 C7 H7A 109.3 . .
N2 C7 H7B 109.3 . .
C8 C7 H7B 109.3 . .
H7A C7 H7B 108.0 . .
N3 C8 C9 121.1(6) . .
N3 C8 C7 117.2(5) . .
C9 C8 C7 121.6(6) . .
C10 C9 C8 119.1(7) . .
C10 C9 H9 120.4 . .
C8 C9 H9 120.4 . .
C9 C10 C11 119.9(6) . .
C9 C10 H10 120.0 . .
C11 C10 H10 120.1 . .
C12 C11 C10 118.8(7) . .
C12 C11 H11 120.6 . .
C10 C11 H11 120.6 . .
C11 C12 N3 122.8(6) . .
C11 C12 H12 118.6 . .
N3 C12 H12 118.6 . .
N2 C13 C14 111.9(4) . .
N2 C13 H13A 109.2 . .
C14 C13 H13A 109.2 . .
N2 C13 H13B 109.3 . .
C14 C13 H13B 109.3 . .
H13A C13 H13B 107.9 . .
O1 C14 C13 106.0(3) . .
O1 C14 H14A 110.5 . .
C13 C14 H14A 110.5 . .
O1 C14 H14B 110.5 . .
C13 C14 H14B 110.5 . .
H14A C14 H14B 108.7 . .
O1 C15 C18 123.0(4) . .
O1 C15 C16 116.8(3) . .
C18 C15 C16 120.2(4) . .
C15 C16 C15 118.9(5) 2 .
C15 C16 C17 120.5(2) 2 .
C15 C16 C17 120.5(2) . .
O2 C17 O2 122.6(5) . 2
O2 C17 C16 118.7(3) . .
O2 C17 C16 118.7(3) 2 .
C19 C18 C15 119.7(5) . .
C19 C18 H18 120.2 . .
C15 C18 H18 120.1 . .
C18 C19 C18 121.3(6) . 2
C18 C19 H19 119.4 . .
C18 C19 H19 119.4 2 .
O2 Ni1 N3 102.99(16) . .
O2 Ni1 N4 86.8(6) . .
N3 Ni1 N4 87.6(6) . .
O2 Ni1 N2 167.52(14) . .
N3 Ni1 N2 82.35(16) . .
N4 Ni1 N2 104.8(6) . .
O2 Ni1 N1 94.03(15) . .
N3 Ni1 N1 162.92(16) . .
N4 Ni1 N1 91.9(6) . .
N2 Ni1 N1 81.27(15) . .
O2 Ni1 O8 92.5(4) . .
N3 Ni1 O8 91.8(5) . .
N4 Ni1 O8 8.0(8) . .
N2 Ni1 O8 98.7(4) . .
N1 Ni1 O8 85.9(4) . .
O2 Ni1 O1 85.45(11) . .
N3 Ni1 O1 86.59(12) . .
N4 Ni1 O1 169.1(5) . .
N2 Ni1 O1 83.60(13) . .
N1 Ni1 O1 96.38(13) . .
O8 Ni1 O1 177.0(3) . .
O6 Cl1 O7' 24(3) . .
O6 Cl1 O4 123.8(13) . .
O7' Cl1 O4 114.3(16) . .
O6 Cl1 O5 119.6(14) . .
O7' Cl1 O5 118.9(17) . .
O4 Cl1 O5 115.8(5) . .
O6 Cl1 O7 82.3(16) . .
O7' Cl1 O7 106(2) . .
O4 Cl1 O7 98.7(6) . .
O5 Cl1 O7 98.5(6) . .
O6 Cl1 O6' 82.4(16) . .
O7' Cl1 O6' 58(2) . .
O4 Cl1 O6' 83.4(10) . .
O5 Cl1 O6' 95.9(12) . .
O7 Cl1 O6' 162.7(11) . .
C1 N1 C5 119.8(5) . .
C1 N1 Ni1 128.1(4) . .
C5 N1 Ni1 111.6(3) . .
C7 N2 C6 113.8(4) . .
C7 N2 C13 113.5(4) . .
C6 N2 C13 109.0(4) . .
C7 N2 Ni1 109.6(3) . .
C6 N2 Ni1 104.9(3) . .
C13 N2 Ni1 105.4(2) . .
C8 N3 C12 118.1(5) . .
C8 N3 Ni1 114.2(4) . .
C12 N3 Ni1 127.6(3) . .
C15 O1 C14 117.1(3) . .
C15 O1 Ni1 122.3(2) . .
C14 O1 Ni1 107.1(2) . .
C17 O2 Ni1 124.6(2) . .
C24 N4 Ni1 166.6(19) . .
N4 C24 C25 168.0(18) . .
C20 O8 C23 96.5(11) . .
C20 O8 Ni1 138.7(11) . .
C23 O8 Ni1 118.0(11) . .
O8 C20 C21 128.6(14) . .
O8 C20 H20A 104.9 . .
C21 C20 H20A 105.2 . .
O8 C20 H20B 105.1 . .
C21 C20 H20B 105.3 . .
H20A C20 H20B 106.0 . .
C22 C21 C20 96.7(13) . .
C22 C21 H21A 112.6 . .
C20 C21 H21A 112.5 . .
C22 C21 H21B 112.2 . .
C20 C21 H21B 112.5 . .
H21A C21 H21B 109.9 . .
C21 C22 C23 109.0(13) . .
C21 C22 H22A 110.1 . .
C23 C22 H22A 110.0 . .
C21 C22 H22B 109.7 . .
C23 C22 H22B 109.8 . .
H22A C22 H22B 108.3 . .
O8 C23 C22 107.8(11) . .
O8 C23 H23A 110.1 . .
C22 C23 H23A 110.3 . .
O8 C23 H23B 110.2 . .
C22 C23 H23B 110.0 . .
H23A C23 H23B 108.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.343(6) .
C1 C2 1.379(8) .
C1 H1 0.9300 .
C2 C3 1.357(10) .
C2 H2 0.9300 .
C3 C4 1.375(10) .
C3 H3 0.9300 .
C4 C5 1.404(8) .
C4 H4 0.9300 .
C5 N1 1.336(6) .
C5 C6 1.493(8) .
C6 N2 1.496(6) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 N2 1.461(7) .
C7 C8 1.517(9) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 N3 1.327(7) .
C8 C9 1.397(8) .
C9 C10 1.349(11) .
C9 H9 0.9300 .
C10 C11 1.364(11) .
C10 H10 0.9300 .
C11 C12 1.351(8) .
C11 H11 0.9300 .
C12 N3 1.351(6) .
C12 H12 0.9300 .
C13 N2 1.500(6) .
C13 C14 1.513(7) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 O1 1.455(5) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 O1 1.381(5) .
C15 C18 1.385(6) .
C15 C16 1.396(5) .
C16 C15 1.396(5) 2
C16 C17 1.515(8) .
C17 O2 1.246(4) .
C17 O2 1.246(4) 2
C18 C19 1.369(6) .
C18 H18 0.9300 .
C19 C18 1.369(6) 2
C19 H19 0.9300 .
Ni1 O2 1.974(3) .
Ni1 N3 2.026(4) .
Ni1 N4 2.11(3) .
Ni1 N2 2.056(3) .
Ni1 N1 2.061(4) .
Ni1 O8 2.089(15) .
Ni1 O1 2.174(3) .
Cl1 O6 1.30(2) .
Cl1 O7' 1.35(2) .
Cl1 O4 1.348(5) .
Cl1 O5 1.360(7) .
Cl1 O7 1.572(10) .
Cl1 O6' 1.58(2) .
N4 C24 1.11(3) .
C24 C25 1.38(2) .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
O8 C20 1.27(2) .
O8 C23 1.50(2) .
C20 C21 1.414(17) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 C22 1.415(19) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 C23 1.49(2) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
