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#$Date: 2016-03-21 09:39:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178626 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/37/4073768.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_4073768
loop_
_publ_author_name
'Liao, Chuang-Yi'
'Chan, Kai-Ting'
'Chang, Yu-Chuan'
'Chen, Chih-Yuan'
'Tu, Cheng-Yi'
'Hu, Ching-Han'
'Lee, Hon Man'
_publ_section_title
;
 Unexpected Solvent-Induced Cis/Trans Isomerization and Catalytic
 Application of a Bis-bidentate Nickel(II) Complex with N-Heterocyclic
 Carbene and Amido Functionalities
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              5826
_journal_paper_doi               10.1021/om700607m
_journal_volume                  26
_journal_year                    2007
_chemical_formula_moiety         'C36 H30 F2 N6 Ni O2, 2(H2 O)'
_chemical_formula_sum            'C36 H34 F2 N6 Ni O4'
_chemical_formula_weight         711.40
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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                 101.777(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.809(3)
_cell_length_b                   15.718(2)
_cell_length_c                   13.543(2)
_cell_measurement_temperature    150(2)
_cell_volume                     3294.4(9)
_computing_cell_refinement       'SAINT v6.280a (Bruker, 2004)'
_computing_data_collection       'APEX2 v1.0-22 (Bruker, 2004)'
_computing_data_reduction        'SAINT v6.280a (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL 5.1'
_computing_publication_material  'SHELXTL 5.1'
_computing_structure_refinement  'SHELXTL 5.1'
_computing_structure_solution    'SHELXTL 5.1 (Sheldrick, 1998)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17457
_diffrn_reflns_theta_full        27.98
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         1.85
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  0.9378
_exptl_absorpt_correction_T_min  0.8288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            parallelepipe
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       yellow
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0309P)²+10.2394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                2982
_reflns_number_total             3976
_reflns_threshold_expression     I>2σ
_cod_data_source_file            om700607m-file002.cif
_cod_data_source_block           2b
_cod_original_cell_volume        3294.6(10)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4073768
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
C1 C 0.0854(2) 0.84357(18) 0.7453(2) 0.0428(8) Uani 1 1 d .
C2 C 0.1993(3) 0.8956(2) 0.6880(4) 0.0732(14) Uani 1 1 d .
H2 H 0.2437 0.9007 0.6505 0.088 Uiso 1 1 calc R
C3 C 0.1832(3) 0.9496(2) 0.7577(4) 0.0775(15) Uani 1 1 d .
H3 H 0.2136 1.0007 0.7792 0.093 Uiso 1 1 calc R
C4 C 0.0784(3) 0.9544(2) 0.8760(3) 0.0710(13) Uani 1 1 d .
H4A H 0.0157 0.9643 0.8525 0.085 Uiso 1 1 calc R
H4B H 0.1062 1.0104 0.8936 0.085 Uiso 1 1 calc R
C5 C 0.0923(3) 0.8997(3) 0.9688(3) 0.0660(12) Uani 1 1 d .
C6 C 0.0241(3) 0.8835(3) 1.0167(3) 0.0694(12) Uani 1 1 d .
H6 H -0.0316 0.9060 0.9897 0.083 Uiso 1 1 calc R
C7 C 0.0369(3) 0.8349(3) 1.1036(3) 0.0806(15) Uani 1 1 d .
H7 H -0.0094 0.8240 1.1368 0.097 Uiso 1 1 calc R
C8 C 0.1176(3) 0.8028(4) 1.1410(3) 0.0867(16) Uani 1 1 d .
C9 C 0.1867(3) 0.8181(4) 1.0954(4) 0.0912(18) Uani 1 1 d .
H9 H 0.2423 0.7956 1.1231 0.109 Uiso 1 1 calc R
C10 C 0.1734(3) 0.8665(3) 1.0096(3) 0.0791(15) Uani 1 1 d .
H10 H 0.2204 0.8776 0.9774 0.095 Uiso 1 1 calc R
C11 C 0.1371(2) 0.75283(17) 0.6217(2) 0.0419(8) Uani 1 1 d .
H11A H 0.1862 0.7523 0.5866 0.050 Uiso 1 1 calc R
H11B H 0.0829 0.7508 0.5701 0.050 Uiso 1 1 calc R
C12 C 0.14224(17) 0.67533(16) 0.68996(18) 0.0272(5) Uani 1 1 d .
C13 C 0.09397(17) 0.6140(2) 0.8294(2) 0.0354(7) Uani 1 1 d .
C14 C 0.0909(2) 0.6426(3) 0.9268(2) 0.0576(10) Uani 1 1 d .
H14 H 0.0852 0.7018 0.9384 0.069 Uiso 1 1 calc R
C15 C 0.0961(3) 0.5871(5) 1.0051(3) 0.0905(19) Uani 1 1 d .
H15 H 0.0941 0.6075 1.0707 0.109 Uiso 1 1 calc R
C16 C 0.1042(2) 0.5028(4) 0.9891(4) 0.100(2) Uani 1 1 d .
H16 H 0.1086 0.4641 1.0438 0.120 Uiso 1 1 calc R
C17 C 0.1059(3) 0.4725(3) 0.8938(5) 0.095(2) Uani 1 1 d .
H17 H 0.1106 0.4131 0.8834 0.114 Uiso 1 1 calc R
C18 C 0.1009(2) 0.5289(2) 0.8121(3) 0.0578(10) Uani 1 1 d .
H18 H 0.1024 0.5082 0.7466 0.069 Uiso 1 1 calc R
F1 F 0.1295(2) 0.7541(3) 1.22547(19) 0.1179(12) Uani 1 1 d .
N1 N 0.13947(19) 0.83095(16) 0.6806(2) 0.0485(7) Uani 1 1 d .
N2 N 0.1133(2) 0.91678(17) 0.7928(2) 0.0573(9) Uani 1 1 d .
N3 N 0.08803(14) 0.67702(14) 0.75340(15) 0.0263(5) Uani 1 1 d .
Ni1 Ni 0.0000 0.76333(3) 0.7500 0.02982(15) Uani 1 2 d S
O1 O 0.19514(12) 0.61839(12) 0.68136(14) 0.0336(4) Uani 1 1 d .
O2 O 0.3098(2) 0.6342(3) 0.5623(3) 0.145(2) Uani 1 1 d D
H1B H 0.2832 0.5972 0.5270 0.174 Uiso 1 1 d D
H1A H 0.2773 0.6395 0.6020 0.174 Uiso 1 1 d 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'
F F 0.0171 0.0103 '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
N2 C1 N1 104.2(3) . .
N2 C1 Ni1 137.0(2) . .
N1 C1 Ni1 118.7(2) . .
C3 C2 N1 107.1(3) . .
C3 C2 H2 126.5 . .
N1 C2 H2 126.5 . .
C2 C3 N2 106.7(3) . .
C2 C3 H3 126.7 . .
N2 C3 H3 126.7 . .
N2 C4 C5 113.3(3) . .
N2 C4 H4A 108.9 . .
C5 C4 H4A 108.9 . .
N2 C4 H4B 108.9 . .
C5 C4 H4B 108.9 . .
H4A C4 H4B 107.7 . .
C10 C5 C6 119.1(5) . .
C10 C5 C4 120.9(4) . .
C6 C5 C4 120.0(4) . .
C7 C6 C5 120.4(5) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C8 C7 C6 118.8(4) . .
C8 C7 H7 120.6 . .
C6 C7 H7 120.6 . .
F1 C8 C7 118.5(5) . .
F1 C8 C9 119.3(5) . .
C7 C8 C9 122.2(5) . .
C10 C9 C8 118.6(5) . .
C10 C9 H9 120.7 . .
C8 C9 H9 120.7 . .
C9 C10 C5 121.0(4) . .
C9 C10 H10 119.5 . .
C5 C10 H10 119.5 . .
N1 C11 C12 110.5(2) . .
N1 C11 H11A 109.6 . .
C12 C11 H11A 109.6 . .
N1 C11 H11B 109.6 . .
C12 C11 H11B 109.6 . .
H11A C11 H11B 108.1 . .
O1 C12 N3 127.4(3) . .
O1 C12 C11 118.2(2) . .
N3 C12 C11 114.5(2) . .
C18 C13 C14 119.6(3) . .
C18 C13 N3 123.8(3) . .
C14 C13 N3 116.7(3) . .
C15 C14 C13 121.2(5) . .
C15 C14 H14 119.4 . .
C13 C14 H14 119.4 . .
C16 C15 C14 119.6(5) . .
C16 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
C15 C16 C17 120.5(4) . .
C15 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
C16 C17 C18 120.6(5) . .
C16 C17 H17 119.7 . .
C18 C17 H17 119.7 . .
C13 C18 C17 118.4(4) . .
C13 C18 H18 120.8 . .
C17 C18 H18 120.8 . .
C1 N1 C2 111.0(3) . .
C1 N1 C11 121.7(2) . .
C2 N1 C11 126.9(3) . .
C1 N2 C3 111.0(3) . .
C1 N2 C4 124.8(3) . .
C3 N2 C4 124.0(3) . .
C12 N3 C13 119.9(2) . .
C12 N3 Ni1 123.53(18) . .
C13 N3 Ni1 116.58(17) . .
C1 Ni1 C1 94.52(19) 2_556 .
C1 Ni1 N3 87.28(11) 2_556 2_556
C1 Ni1 N3 176.32(11) . 2_556
C1 Ni1 N3 176.32(11) 2_556 .
C1 Ni1 N3 87.28(11) . .
N3 Ni1 N3 91.10(13) 2_556 .
H1B O2 H1A 98.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.348(4) .
C1 N1 1.357(4) .
C1 Ni1 1.858(3) .
C2 C3 1.333(5) .
C2 N1 1.378(4) .
C2 H2 0.9500 .
C3 N2 1.388(4) .
C3 H3 0.9500 .
C4 N2 1.475(4) .
C4 C5 1.502(6) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C10 1.390(6) .
C5 C6 1.391(5) .
C6 C7 1.383(7) .
C6 H6 0.9500 .
C7 C8 1.369(7) .
C7 H7 0.9500 .
C8 F1 1.358(6) .
C8 C9 1.381(6) .
C9 C10 1.369(7) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C11 N1 1.460(4) .
C11 C12 1.521(4) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 O1 1.246(3) .
C12 N3 1.332(3) .
C13 C18 1.367(5) .
C13 C14 1.404(4) .
C13 N3 1.418(3) .
C14 C15 1.363(5) .
C14 H14 0.9500 .
C15 C16 1.353(8) .
C15 H15 0.9500 .
C16 C17 1.381(8) .
C16 H16 0.9500 .
C17 C18 1.406(5) .
C17 H17 0.9500 .
C18 H18 0.9500 .
N3 Ni1 1.937(2) .
Ni1 C1 1.858(3) 2_556
Ni1 N3 1.937(2) 2_556
O2 H1B 0.8142 .
O2 H1A 0.8203 .
