#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:16:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178600 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/11/4071167.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_4071167
loop_
_publ_author_name
'Huynh, Han Vinh'
'Wong, Ling Rong'
'Ng, Pearly Shuyi'
_publ_section_title
;
 Anagostic Interactions and Catalytic Activities of Sterically Bulky
 Benzannulated N-Heterocyclic Carbene Complexes of Nickel(II)
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              2231
_journal_paper_doi               10.1021/om800004j
_journal_volume                  27
_journal_year                    2008
_chemical_formula_sum            'C60 H58 Br2 N6 Ni O2'
_chemical_formula_weight         1113.65
_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                 94.9870(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.5341(5)
_cell_length_b                   17.8161(8)
_cell_length_c                   14.2407(7)
_cell_measurement_reflns_used    2981
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      22.81
_cell_measurement_theta_min      2.31
_cell_volume                     2662.5(2)
_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      223(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18906
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    1.914
_exptl_absorpt_correction_T_max  0.7008
_exptl_absorpt_correction_T_min  0.5148
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            ORANGE
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.915
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         6117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0691P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                3876
_reflns_number_total             6117
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800004j-file008.cif
_cod_data_source_block           Complex12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4071167
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 0.5000 0.5000 0.5000 0.03816(16) Uani 1 2 d S
Br1 Br 0.70311(3) 0.53157(2) 0.56135(3) 0.05798(14) Uani 1 1 d .
N1 N 0.4427(2) 0.65954(13) 0.51150(17) 0.0411(6) Uani 1 1 d .
N2 N 0.3887(2) 0.60000(13) 0.63432(17) 0.0417(6) Uani 1 1 d .
C1 C 0.4391(3) 0.59061(15) 0.5506(2) 0.0395(7) Uani 1 1 d .
C2 C 0.3976(3) 0.71329(17) 0.5697(2) 0.0455(8) Uani 1 1 d .
C3 C 0.3887(3) 0.79117(19) 0.5611(3) 0.0592(9) Uani 1 1 d .
H3 H 0.4135 0.8165 0.5077 0.071 Uiso 1 1 calc R
C4 C 0.3412(4) 0.8293(2) 0.6354(3) 0.0718(11) Uani 1 1 d .
H4 H 0.3334 0.8818 0.6324 0.086 Uiso 1 1 calc R
C5 C 0.3052(4) 0.7919(2) 0.7137(3) 0.0737(11) Uani 1 1 d .
H5 H 0.2731 0.8199 0.7623 0.088 Uiso 1 1 calc R
C6 C 0.3145(4) 0.7152(2) 0.7232(3) 0.0604(9) Uani 1 1 d .
H6 H 0.2902 0.6904 0.7771 0.073 Uiso 1 1 calc R
C7 C 0.3617(3) 0.67624(17) 0.6491(2) 0.0471(8) Uani 1 1 d .
C8 C 0.4953(3) 0.67535(18) 0.4214(2) 0.0502(8) Uani 1 1 d .
H8A H 0.5339 0.6294 0.3991 0.060 Uiso 1 1 calc R
H8B H 0.5629 0.7129 0.4319 0.060 Uiso 1 1 calc R
C9 C 0.3984(3) 0.70336(18) 0.3460(2) 0.0479(8) Uani 1 1 d .
C10 C 0.4212(4) 0.7675(2) 0.2962(3) 0.0674(11) Uani 1 1 d .
H10 H 0.4968 0.7946 0.3109 0.081 Uiso 1 1 calc R
C11 C 0.3341(5) 0.7925(3) 0.2249(3) 0.0915(15) Uani 1 1 d .
H11 H 0.3502 0.8369 0.1923 0.110 Uiso 1 1 calc R
C12 C 0.2248(5) 0.7530(3) 0.2018(3) 0.0863(14) Uani 1 1 d .
H12 H 0.1661 0.7697 0.1527 0.104 Uiso 1 1 calc R
C13 C 0.2017(4) 0.6901(3) 0.2493(3) 0.0898(14) Uani 1 1 d .
H13 H 0.1265 0.6629 0.2332 0.108 Uiso 1 1 calc R
C14 C 0.2866(4) 0.6651(2) 0.3215(3) 0.0742(12) Uani 1 1 d .
H14 H 0.2681 0.6213 0.3545 0.089 Uiso 1 1 calc R
C15 C 0.3756(3) 0.53679(16) 0.6991(2) 0.0476(8) Uani 1 1 d .
H15 H 0.3817 0.4913 0.6598 0.057 Uiso 1 1 calc R
C16 C 0.2431(3) 0.53302(18) 0.7349(3) 0.0509(8) Uani 1 1 d .
C17 C 0.2197(4) 0.5535(2) 0.8248(3) 0.0660(10) Uani 1 1 d .
H17 H 0.2869 0.5711 0.8668 0.079 Uiso 1 1 calc R
C18 C 0.0987(5) 0.5483(2) 0.8537(4) 0.0854(14) Uani 1 1 d .
H18 H 0.0833 0.5630 0.9151 0.102 Uiso 1 1 calc R
C19 C 0.0000(5) 0.5216(3) 0.7928(5) 0.1005(18) Uani 1 1 d .
H19 H -0.0826 0.5181 0.8127 0.121 Uiso 1 1 calc R
C20 C 0.0221(5) 0.5005(3) 0.7047(4) 0.0960(15) Uani 1 1 d .
H20 H -0.0452 0.4823 0.6633 0.115 Uiso 1 1 calc R
C21 C 0.1431(4) 0.5056(2) 0.6750(3) 0.0720(11) Uani 1 1 d .
H21 H 0.1578 0.4904 0.6137 0.086 Uiso 1 1 calc R
C22 C 0.4847(3) 0.5303(2) 0.7754(2) 0.0592(10) Uani 1 1 d .
C23 C 0.5025(5) 0.4630(3) 0.8213(4) 0.127(2) Uani 1 1 d .
H23 H 0.4476 0.4225 0.8052 0.153 Uiso 1 1 calc R
C24 C 0.6013(7) 0.4545(5) 0.8917(5) 0.175(4) Uani 1 1 d .
H24 H 0.6116 0.4085 0.9239 0.210 Uiso 1 1 calc R
C25 C 0.6835(6) 0.5119(5) 0.9147(4) 0.138(3) Uani 1 1 d .
H25 H 0.7496 0.5064 0.9629 0.166 Uiso 1 1 calc R
C26 C 0.6681(5) 0.5756(4) 0.8676(4) 0.1112(18) Uani 1 1 d .
H26 H 0.7256 0.6152 0.8821 0.133 Uiso 1 1 calc R
C27 C 0.5692(4) 0.5860(3) 0.7971(3) 0.0830(13) Uani 1 1 d .
H27 H 0.5612 0.6319 0.7646 0.100 Uiso 1 1 calc R
N1S N 0.4593(4) 0.7812(2) 0.9907(3) 0.0874(11) Uani 1 1 d .
O1S O 0.2735(3) 0.7207(2) 0.9500(2) 0.1007(11) Uani 1 1 d .
C1S C 0.3370(5) 0.7755(4) 0.9718(3) 0.0980(16) Uani 1 1 d .
H1S H 0.2912 0.8205 0.9756 0.118 Uiso 1 1 calc R
C2S C 0.5242(6) 0.8506(3) 1.0184(5) 0.140(2) Uani 1 1 d .
H2S1 H 0.5777 0.8658 0.9697 0.210 Uiso 1 1 calc R
H2S2 H 0.5766 0.8429 1.0771 0.210 Uiso 1 1 calc R
H2S3 H 0.4617 0.8894 1.0270 0.210 Uiso 1 1 calc R
C3S C 0.5369(7) 0.7182(4) 0.9830(7) 0.208(4) Uani 1 1 d .
H3S1 H 0.4844 0.6752 0.9639 0.312 Uiso 1 1 calc R
H3S2 H 0.5833 0.7081 1.0435 0.312 Uiso 1 1 calc R
H3S3 H 0.5967 0.7277 0.9364 0.312 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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
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
C1 Ni1 C1 180.000(1) 3_666 .
C1 Ni1 Br1 91.05(8) 3_666 .
C1 Ni1 Br1 88.95(8) . .
C1 Ni1 Br1 88.95(8) 3_666 3_666
C1 Ni1 Br1 91.05(8) . 3_666
Br1 Ni1 Br1 180.0 . 3_666
C1 N1 C2 111.1(3) . .
C1 N1 C8 124.1(3) . .
C2 N1 C8 124.6(2) . .
C1 N2 C7 110.5(2) . .
C1 N2 C15 121.5(2) . .
C7 N2 C15 127.9(3) . .
N1 C1 N2 106.1(2) . .
N1 C1 Ni1 126.4(2) . .
N2 C1 Ni1 127.5(2) . .
N1 C2 C7 107.0(3) . .
N1 C2 C3 131.5(3) . .
C7 C2 C3 121.5(3) . .
C4 C3 C2 116.5(3) . .
C5 C4 C3 121.5(3) . .
C6 C5 C4 122.5(4) . .
C5 C6 C7 116.6(3) . .
C2 C7 C6 121.4(3) . .
C2 C7 N2 105.3(3) . .
C6 C7 N2 133.3(3) . .
N1 C8 C9 113.9(3) . .
C10 C9 C14 117.6(3) . .
C10 C9 C8 120.4(3) . .
C14 C9 C8 121.9(3) . .
C9 C10 C11 120.8(4) . .
C12 C11 C10 120.2(4) . .
C13 C12 C11 119.7(4) . .
C12 C13 C14 120.8(4) . .
C13 C14 C9 120.9(4) . .
N2 C15 C22 113.7(3) . .
N2 C15 C16 112.4(2) . .
C22 C15 C16 114.5(3) . .
C17 C16 C21 118.6(4) . .
C17 C16 C15 122.8(3) . .
C21 C16 C15 118.5(3) . .
C16 C17 C18 120.4(4) . .
C17 C18 C19 120.2(5) . .
C20 C19 C18 119.9(5) . .
C19 C20 C21 120.3(5) . .
C20 C21 C16 120.5(5) . .
C27 C22 C23 118.3(4) . .
C27 C22 C15 123.4(3) . .
C23 C22 C15 118.2(4) . .
C22 C23 C24 120.1(6) . .
C25 C24 C23 120.8(6) . .
C26 C25 C24 118.5(5) . .
C25 C26 C27 122.0(6) . .
C22 C27 C26 120.2(5) . .
C1S N1S C3S 119.9(5) . .
C1S N1S C2S 124.0(5) . .
C3S N1S C2S 116.1(5) . .
O1S C1S N1S 129.4(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 C1 1.902(3) 3_666
Ni1 C1 1.902(3) .
Ni1 Br1 2.3092(3) .
Ni1 Br1 2.3092(3) 3_666
N1 C1 1.350(3) .
N1 C2 1.378(4) .
N1 C8 1.468(4) .
N2 C1 1.357(4) .
N2 C7 1.407(4) .
N2 C15 1.470(4) .
C2 C7 1.390(4) .
C2 C3 1.395(4) .
C3 C4 1.387(5) .
C4 C5 1.380(6) .
C5 C6 1.376(5) .
C6 C7 1.391(5) .
C8 C9 1.501(4) .
C9 C10 1.377(5) .
C9 C14 1.379(5) .
C10 C11 1.381(5) .
C11 C12 1.366(6) .
C12 C13 1.342(6) .
C13 C14 1.377(5) .
C15 C22 1.517(5) .
C15 C16 1.529(5) .
C16 C17 1.373(5) .
C16 C21 1.385(5) .
C17 C18 1.377(6) .
C18 C19 1.379(7) .
C19 C20 1.350(7) .
C20 C21 1.380(6) .
C22 C27 1.350(5) .
C22 C23 1.371(6) .
C23 C24 1.389(8) .
C24 C25 1.362(10) .
C25 C26 1.320(8) .
C26 C27 1.396(6) .
N1S C1S 1.297(6) .
N1S C3S 1.398(7) .
N1S C2S 1.451(6) .
O1S C1S 1.209(6) .
