#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/82/4068298.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_4068298
loop_
_publ_author_name
'Ojwach, Stephen O.'
'Guzei, Ilia A.'
'Benade, Letitia L.'
'Mapolie, Selwyn F.'
'Darkwa, James'
_publ_section_title
;
 (Pyrazol-1-ylmethyl)pyridine Nickel Complexes: Ethylene Oligomerization
 and Unusual Friedel−Crafts Alkylation Catalysts
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              2127
_journal_paper_doi               10.1021/om8006322
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C22 H26 Br4 N6 Ni2'
_chemical_formula_sum            'C22 H26 Br4 N6 Ni2'
_chemical_formula_weight         811.55
_chemical_name_systematic
; 
 ? 
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                71.8750(10)
_cell_angle_beta                 72.8330(10)
_cell_angle_gamma                83.9380(10)
_cell_formula_units_Z            1
_cell_length_a                   7.4989(6)
_cell_length_b                   8.6632(7)
_cell_length_c                   10.9434(9)
_cell_measurement_reflns_used    6098
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2686
_cell_measurement_theta_min      2.4740
_cell_volume                     645.48(9)
_computing_cell_refinement       'SAINT Ver. 6.22  (Bruker-AXS, 2003)'
_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_molecular_graphics    'SHELXTL Ver. 6.10'
_computing_publication_material  'SHELXTL Ver. 6.10'
_computing_structure_refinement  'SHELXTL Ver. 6.10'
_computing_structure_solution    'SHELXTL Ver. 6.10 (Bruker-AXS, 2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker CCD-1000 area detector'
_diffrn_measurement_method       '0.30° ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8518
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.673
_exptl_absorpt_correction_T_max  0.4595
_exptl_absorpt_correction_T_min  0.1263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2003)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.088
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0187
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0303P)²+0.2871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0488
_refine_ls_wR_factor_ref         0.0497
_reflns_number_gt                2923
_reflns_number_total             3115
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om8006322_si_001.cif
_cod_data_source_block           darkwa42
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-P 1        '
_cod_original_sg_symbol_H-M      'P -1        '
_cod_database_code               4068298
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
Ni1 Ni 0.39118(3) 0.10132(2) 0.35474(2) 0.01036(6) Uani 1 1 d .
Br1 Br 0.28209(2) -0.059479(19) 0.247315(18) 0.01549(6) Uani 1 1 d .
Br2 Br 0.35583(2) 0.116798(19) 0.585261(17) 0.01406(6) Uani 1 1 d .
N1 N 0.5663(2) 0.26706(17) 0.21187(15) 0.0121(3) Uani 1 1 d .
N2 N 0.5373(2) 0.42891(16) 0.20245(15) 0.0112(3) Uani 1 1 d .
N3 N 0.1744(2) 0.27022(17) 0.34458(15) 0.0118(3) Uani 1 1 d .
C1 C 0.7856(3) 0.1042(2) 0.0792(2) 0.0187(4) Uani 1 1 d .
H1A H 0.8483 0.1249 -0.0165 0.028 Uiso 1 1 calc R
H1B H 0.6828 0.0290 0.1054 0.028 Uiso 1 1 calc R
H1C H 0.8751 0.0563 0.1308 0.028 Uiso 1 1 calc R
C2 C 0.7105(2) 0.2600(2) 0.10652(18) 0.0131(3) Uani 1 1 d .
C3 C 0.7733(2) 0.4168(2) 0.03131(18) 0.0146(3) Uani 1 1 d .
H3 H 0.8735 0.4452 -0.0482 0.018 Uiso 1 1 calc R
C4 C 0.6621(2) 0.5220(2) 0.09449(18) 0.0136(3) Uani 1 1 d .
C5 C 0.6677(3) 0.7018(2) 0.0613(2) 0.0198(4) Uani 1 1 d .
H5A H 0.5458 0.7488 0.0525 0.030 Uiso 1 1 calc R
H5B H 0.7634 0.7447 -0.0233 0.030 Uiso 1 1 calc R
H5C H 0.6978 0.7304 0.1328 0.030 Uiso 1 1 calc R
C6 C 0.3955(2) 0.4805(2) 0.30604(18) 0.0122(3) Uani 1 1 d .
H6A H 0.3970 0.6004 0.2830 0.015 Uiso 1 1 calc R
H6B H 0.4279 0.4350 0.3919 0.015 Uiso 1 1 calc R
C7 C 0.2004(2) 0.4288(2) 0.32483(16) 0.0107(3) Uani 1 1 d .
C8 C 0.0533(2) 0.5408(2) 0.32845(17) 0.0135(3) Uani 1 1 d .
H8 H 0.0755 0.6524 0.3122 0.016 Uiso 1 1 calc R
C9 C -0.1263(2) 0.4875(2) 0.35611(18) 0.0143(3) Uani 1 1 d .
H9 H -0.2290 0.5618 0.3598 0.017 Uiso 1 1 calc R
C10 C -0.1537(3) 0.3243(2) 0.37828(19) 0.0154(3) Uani 1 1 d .
H10 H -0.2756 0.2845 0.3990 0.019 Uiso 1 1 calc R
C11 C 0.0000(2) 0.2204(2) 0.36973(18) 0.0138(3) Uani 1 1 d .
H11 H -0.0186 0.1091 0.3822 0.017 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'
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_3
_geom_angle_publ_flag
N1 Ni1 N3 89.42(6) . yes
N1 Ni1 Br1 107.81(4) . yes
N3 Ni1 Br1 94.14(4) . yes
N1 Ni1 Br2 112.99(4) . yes
N3 Ni1 Br2 87.52(4) . yes
Br1 Ni1 Br2 139.180(11) . yes
N1 Ni1 Br2 96.93(4) 2_656 yes
N3 Ni1 Br2 169.41(4) 2_656 yes
Br1 Ni1 Br2 91.984(10) 2_656 yes
Br2 Ni1 Br2 82.205(9) 2_656 yes
Ni1 Br2 Ni1 97.794(9) 2_656 yes
C2 N1 N2 105.78(13) . ?
C2 N1 Ni1 133.79(12) . ?
N2 N1 Ni1 120.16(11) . ?
C4 N2 N1 111.29(14) . ?
C4 N2 C6 128.07(14) . ?
N1 N2 C6 120.48(13) . ?
C11 N3 C7 118.35(15) . ?
C11 N3 Ni1 119.84(12) . ?
C7 N3 Ni1 121.55(11) . ?
C2 C1 H1A 109.5 . ?
C2 C1 H1B 109.5 . ?
H1A C1 H1B 109.5 . ?
C2 C1 H1C 109.5 . ?
H1A C1 H1C 109.5 . ?
H1B C1 H1C 109.5 . ?
N1 C2 C3 109.75(15) . ?
N1 C2 C1 122.76(16) . ?
C3 C2 C1 127.48(16) . ?
C4 C3 C2 106.89(15) . ?
C4 C3 H3 126.6 . ?
C2 C3 H3 126.6 . ?
N2 C4 C3 106.27(15) . ?
N2 C4 C5 123.22(16) . ?
C3 C4 C5 130.50(16) . ?
C4 C5 H5A 109.5 . ?
C4 C5 H5B 109.5 . ?
H5A C5 H5B 109.5 . ?
C4 C5 H5C 109.5 . ?
H5A C5 H5C 109.5 . ?
H5B C5 H5C 109.5 . ?
N2 C6 C7 113.75(14) . ?
N2 C6 H6A 108.8 . ?
C7 C6 H6A 108.8 . ?
N2 C6 H6B 108.8 . ?
C7 C6 H6B 108.8 . ?
H6A C6 H6B 107.7 . ?
N3 C7 C8 122.02(15) . ?
N3 C7 C6 117.54(15) . ?
C8 C7 C6 120.35(15) . ?
C9 C8 C7 119.06(15) . ?
C9 C8 H8 120.5 . ?
C7 C8 H8 120.5 . ?
C10 C9 C8 119.03(16) . ?
C10 C9 H9 120.5 . ?
C8 C9 H9 120.5 . ?
C9 C10 C11 118.75(16) . ?
C9 C10 H10 120.6 . ?
C11 C10 H10 120.6 . ?
N3 C11 C10 122.76(16) . ?
N3 C11 H11 118.6 . ?
C10 C11 H11 118.6 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 2.0052(15) . yes
Ni1 N3 2.0733(14) . yes
Ni1 Br1 2.4123(3) . yes
Ni1 Br2 2.5021(3) . yes
Ni1 Br2 2.6090(3) 2_656 yes
Br2 Ni1 2.6090(3) 2_656 yes
N1 C2 1.340(2) . ?
N1 N2 1.3722(19) . ?
N2 C4 1.355(2) . ?
N2 C6 1.455(2) . ?
N3 C11 1.344(2) . ?
N3 C7 1.349(2) . ?
C1 C2 1.490(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.398(2) . ?
C3 C4 1.377(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.487(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.512(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.390(2) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
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_4
N1 Ni1 Br2 Ni1 -94.25(5) . 2_656
N3 Ni1 Br2 Ni1 177.43(4) . 2_656
Br1 Ni1 Br2 Ni1 83.971(17) . 2_656
Br2 Ni1 Br2 Ni1 0.0 2_656 2_656
N3 Ni1 N1 C2 -141.29(17) . .
Br1 Ni1 N1 C2 -47.13(17) . .
Br2 Ni1 N1 C2 131.65(16) . .
Br2 Ni1 N1 C2 47.21(17) 2_656 .
N3 Ni1 N1 N2 31.84(13) . .
Br1 Ni1 N1 N2 126.01(11) . .
Br2 Ni1 N1 N2 -55.21(13) . .
Br2 Ni1 N1 N2 -139.65(12) 2_656 .
C2 N1 N2 C4 -0.82(19) . .
Ni1 N1 N2 C4 -175.68(11) . .
C2 N1 N2 C6 -176.72(15) . .
Ni1 N1 N2 C6 8.4(2) . .
N1 Ni1 N3 C11 148.70(14) . .
Br1 Ni1 N3 C11 40.88(13) . .
Br2 Ni1 N3 C11 -98.26(13) . .
Br2 Ni1 N3 C11 -84.3(3) 2_656 .
N1 Ni1 N3 C7 -37.28(14) . .
Br1 Ni1 N3 C7 -145.09(13) . .
Br2 Ni1 N3 C7 75.77(13) . .
Br2 Ni1 N3 C7 89.7(3) 2_656 .
N2 N1 C2 C3 0.43(19) . .
Ni1 N1 C2 C3 174.27(13) . .
N2 N1 C2 C1 -179.44(16) . .
Ni1 N1 C2 C1 -5.6(3) . .
N1 C2 C3 C4 0.1(2) . .
C1 C2 C3 C4 179.95(18) . .
N1 N2 C4 C3 0.9(2) . .
C6 N2 C4 C3 176.38(16) . .
N1 N2 C4 C5 -178.13(16) . .
C6 N2 C4 C5 -2.6(3) . .
C2 C3 C4 N2 -0.6(2) . .
C2 C3 C4 C5 178.33(18) . .
C4 N2 C6 C7 125.14(18) . .
N1 N2 C6 C7 -59.7(2) . .
C11 N3 C7 C8 -0.7(3) . .
Ni1 N3 C7 C8 -174.78(12) . .
C11 N3 C7 C6 175.93(15) . .
Ni1 N3 C7 C6 1.8(2) . .
N2 C6 C7 N3 52.5(2) . .
N2 C6 C7 C8 -130.82(16) . .
N3 C7 C8 C9 1.5(3) . .
C6 C7 C8 C9 -175.06(16) . .
C7 C8 C9 C10 -0.5(3) . .
C8 C9 C10 C11 -1.1(3) . .
C7 N3 C11 C10 -1.1(3) . .
Ni1 N3 C11 C10 173.15(14) . .
C9 C10 C11 N3 2.0(3) . .
