#------------------------------------------------------------------------------
#$Date: 2019-11-24 08:23:09 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237283 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/81/4088113.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_4088113
loop_
_publ_author_name
'Astakhov, Alexander V.'
'Khazipov, Oleg V.'
'Degtyareva, Evgeniya S.'
'Khrustalev, Victor N.'
'Chernyshev, Victor M.'
'Ananikov, Valentine P.'
_publ_section_title
;
 Facile Hydrolysis of Nickel(II) Complexes with N-Heterocyclic Carbene
 Ligands
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              5759
_journal_paper_doi               10.1021/acs.organomet.5b00856
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C30 H44 Br2 N4 Ni'
_chemical_formula_sum            'C30 H44 Br2 N4 Ni'
_chemical_formula_weight         679.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 117.4590(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.8444(9)
_cell_length_b                   8.6503(6)
_cell_length_c                   14.2728(10)
_cell_measurement_reflns_used    3691
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.35
_cell_measurement_theta_min      2.85
_cell_volume                     1516.72(18)
_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-2014/7 (Sheldrick, 2014)'
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19099
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         1.658
_exptl_absorpt_coefficient_mu    3.299
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       plate
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.950
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         4427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0605P)²+0.5122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3273
_reflns_number_total             4427
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00856_si_004.cif
_cod_data_source_block           5d
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4088113
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.438
_shelx_estimated_absorpt_t_max   0.852
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Br1 Br 0.51230(3) 0.76536(4) 0.50690(2) 0.02701(10) Uani 1 1 d . . .
Ni1 Ni 0.5000 0.5000 0.5000 0.01669(12) Uani 1 2 d S . P
N1 N 0.29780(18) 0.5557(3) 0.51013(18) 0.0186(5) Uani 1 1 d . . .
C2 C 0.4034(2) 0.5111(3) 0.5608(2) 0.0186(5) Uani 1 1 d . . .
N3 N 0.42481(19) 0.4817(3) 0.66207(18) 0.0185(5) Uani 1 1 d . . .
C3A C 0.3334(2) 0.5105(3) 0.6762(2) 0.0191(5) Uani 1 1 d . . .
C4 C 0.3147(3) 0.4995(3) 0.7639(2) 0.0247(6) Uani 1 1 d . . .
H4 H 0.3705 0.4689 0.8310 0.030 Uiso 1 1 calc R U .
C5 C 0.2112(3) 0.5353(4) 0.7486(3) 0.0268(6) Uani 1 1 d . . .
H5 H 0.1958 0.5300 0.8069 0.032 Uiso 1 1 calc R U .
C6 C 0.1290(2) 0.5787(4) 0.6503(2) 0.0261(6) Uani 1 1 d . . .
H6 H 0.0588 0.6011 0.6432 0.031 Uiso 1 1 calc R U .
C7 C 0.1464(2) 0.5905(3) 0.5622(2) 0.0234(6) Uani 1 1 d . . .
H7 H 0.0901 0.6206 0.4952 0.028 Uiso 1 1 calc R U .
C7A C 0.2512(2) 0.5554(3) 0.5777(2) 0.0185(5) Uani 1 1 d . . .
C8 C 0.2383(2) 0.5927(3) 0.3975(2) 0.0208(6) Uani 1 1 d . . .
H8A H 0.2907 0.6243 0.3719 0.025 Uiso 1 1 calc R U .
H8B H 0.1890 0.6810 0.3874 0.025 Uiso 1 1 calc R U .
C9 C 0.1716(2) 0.4554(3) 0.3321(2) 0.0228(6) Uani 1 1 d . . .
H9A H 0.2217 0.3727 0.3336 0.027 Uiso 1 1 calc R U .
H9B H 0.1272 0.4138 0.3643 0.027 Uiso 1 1 calc R U .
C10 C 0.0975(3) 0.4997(3) 0.2187(2) 0.0272(6) Uani 1 1 d . . .
H10A H 0.1419 0.5413 0.1865 0.033 Uiso 1 1 calc R U .
H10B H 0.0474 0.5824 0.2173 0.033 Uiso 1 1 calc R U .
C11 C 0.0303(3) 0.3620(4) 0.1528(3) 0.0311(7) Uani 1 1 d . . .
H11A H -0.0160 0.3958 0.0800 0.047 Uiso 1 1 calc R U .
H11B H -0.0154 0.3222 0.1832 0.047 Uiso 1 1 calc R U .
H11C H 0.0795 0.2803 0.1531 0.047 Uiso 1 1 calc R U .
C12 C 0.5295(2) 0.4279(3) 0.7465(2) 0.0191(5) Uani 1 1 d . . .
H12A H 0.5678 0.3676 0.7147 0.023 Uiso 1 1 calc R U .
H12B H 0.5156 0.3580 0.7939 0.023 Uiso 1 1 calc R U .
C13 C 0.6032(2) 0.5596(3) 0.8118(2) 0.0201(5) Uani 1 1 d . . .
H13A H 0.6283 0.6188 0.7677 0.024 Uiso 1 1 calc R U .
H13B H 0.5612 0.6305 0.8336 0.024 Uiso 1 1 calc R U .
C14 C 0.7017(2) 0.4999(3) 0.9096(2) 0.0239(6) Uani 1 1 d . . .
H14A H 0.7433 0.4278 0.8879 0.029 Uiso 1 1 calc R U .
H14B H 0.6767 0.4419 0.9542 0.029 Uiso 1 1 calc R U .
C15 C 0.7761(2) 0.6317(4) 0.9740(3) 0.0291(7) Uani 1 1 d . . .
H15A H 0.8407 0.5890 1.0338 0.044 Uiso 1 1 calc R U .
H15B H 0.7369 0.6988 1.0003 0.044 Uiso 1 1 calc R U .
H15C H 0.7985 0.6921 0.9292 0.044 Uiso 1 1 calc R U .
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'
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
C2 Ni1 C2 180.00(15) 3_666 .
C2 Ni1 Br1 89.08(8) 3_666 3_666
C2 Ni1 Br1 90.92(8) . 3_666
C2 Ni1 Br1 90.92(8) 3_666 .
C2 Ni1 Br1 89.08(8) . .
Br1 Ni1 Br1 180.0 3_666 .
C2 N1 C7A 111.2(2) . .
C2 N1 C8 124.8(2) . .
C7A N1 C8 123.9(2) . .
N1 C2 N3 105.9(2) . .
N1 C2 Ni1 125.7(2) . .
N3 C2 Ni1 128.4(2) . .
C2 N3 C3A 110.7(2) . .
C2 N3 C12 125.5(2) . .
C3A N3 C12 123.8(2) . .
C4 C3A N3 132.5(3) . .
C4 C3A C7A 121.4(3) . .
N3 C3A C7A 106.1(2) . .
C5 C4 C3A 116.9(3) . .
C5 C4 H4 121.6 . .
C3A C4 H4 121.6 . .
C4 C5 C6 121.7(3) . .
C4 C5 H5 119.1 . .
C6 C5 H5 119.1 . .
C7 C6 C5 122.1(3) . .
C7 C6 H6 118.9 . .
C5 C6 H6 118.9 . .
C6 C7 C7A 116.2(3) . .
C6 C7 H7 121.9 . .
C7A C7 H7 121.9 . .
N1 C7A C3A 106.1(2) . .
N1 C7A C7 132.2(3) . .
C3A C7A C7 121.7(3) . .
N1 C8 C9 112.1(2) . .
N1 C8 H8A 109.2 . .
C9 C8 H8A 109.2 . .
N1 C8 H8B 109.2 . .
C9 C8 H8B 109.2 . .
H8A C8 H8B 107.9 . .
C10 C9 C8 112.1(2) . .
C10 C9 H9A 109.2 . .
C8 C9 H9A 109.2 . .
C10 C9 H9B 109.2 . .
C8 C9 H9B 109.2 . .
H9A C9 H9B 107.9 . .
C9 C10 C11 112.3(3) . .
C9 C10 H10A 109.1 . .
C11 C10 H10A 109.1 . .
C9 C10 H10B 109.1 . .
C11 C10 H10B 109.1 . .
H10A C10 H10B 107.9 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N3 C12 C13 113.2(2) . .
N3 C12 H12A 108.9 . .
C13 C12 H12A 108.9 . .
N3 C12 H12B 108.9 . .
C13 C12 H12B 108.9 . .
H12A C12 H12B 107.8 . .
C14 C13 C12 111.7(2) . .
C14 C13 H13A 109.3 . .
C12 C13 H13A 109.3 . .
C14 C13 H13B 109.3 . .
C12 C13 H13B 109.3 . .
H13A C13 H13B 107.9 . .
C13 C14 C15 111.6(2) . .
C13 C14 H14A 109.3 . .
C15 C14 H14A 109.3 . .
C13 C14 H14B 109.3 . .
C15 C14 H14B 109.3 . .
H14A C14 H14B 108.0 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 Ni1 2.3005(4) .
Ni1 C2 1.903(3) 3_666
Ni1 C2 1.903(3) .
Ni1 Br1 2.3005(4) 3_666
N1 C2 1.354(4) .
N1 C7A 1.386(3) .
N1 C8 1.465(3) .
C2 N3 1.359(3) .
N3 C3A 1.393(4) .
N3 C12 1.470(3) .
C3A C4 1.393(4) .
C3A C7A 1.395(4) .
C4 C5 1.382(4) .
C4 H4 0.9500 .
C5 C6 1.390(4) .
C5 H5 0.9500 .
C6 C7 1.389(4) .
C6 H6 0.9500 .
C7 C7A 1.397(4) .
C7 H7 0.9500 .
C8 C9 1.529(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.513(4) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.536(4) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.526(4) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.523(4) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.528(4) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
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
C7A N1 C2 N3 0.1(3)
C8 N1 C2 N3 -177.3(2)
C7A N1 C2 Ni1 -178.21(19)
C8 N1 C2 Ni1 4.5(4)
N1 C2 N3 C3A -1.2(3)
Ni1 C2 N3 C3A 177.02(19)
N1 C2 N3 C12 179.3(2)
Ni1 C2 N3 C12 -2.5(4)
C2 N3 C3A C4 -179.3(3)
C12 N3 C3A C4 0.2(4)
C2 N3 C3A C7A 1.8(3)
C12 N3 C3A C7A -178.6(2)
N3 C3A C4 C5 -178.8(3)
C7A C3A C4 C5 -0.1(4)
C3A C4 C5 C6 0.6(4)
C4 C5 C6 C7 -0.7(5)
C5 C6 C7 C7A 0.3(4)
C2 N1 C7A C3A 1.1(3)
C8 N1 C7A C3A 178.4(2)
C2 N1 C7A C7 -179.3(3)
C8 N1 C7A C7 -2.0(5)
C4 C3A C7A N1 179.3(2)
N3 C3A C7A N1 -1.7(3)
C4 C3A C7A C7 -0.3(4)
N3 C3A C7A C7 178.6(3)
C6 C7 C7A N1 -179.3(3)
C6 C7 C7A C3A 0.2(4)
C2 N1 C8 C9 96.7(3)
C7A N1 C8 C9 -80.2(3)
N1 C8 C9 C10 171.6(3)
C8 C9 C10 C11 -180.0(3)
C2 N3 C12 C13 92.9(3)
C3A N3 C12 C13 -86.6(3)
N3 C12 C13 C14 170.1(2)
C12 C13 C14 C15 179.2(2)
