#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:54:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178587 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/98/4069883.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_4069883
loop_
_publ_author_name
'Hsieh, Chang-Chih'
'Lee, Chia-Jung'
'Horng, Yih-Chern'
_publ_section_title
;
 Effects of the Counteranion on the Pyrazole−Nitrile Coupling
 Reaction Mediated by Nickel(II) Ions
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4923
_journal_paper_doi               10.1021/om9004753
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C16 H22 B2 F8 N10 Ni'
_chemical_formula_weight         586.77
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 97.092(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1198(9)
_cell_length_b                   15.3981(14)
_cell_length_c                   7.7713(7)
_cell_measurement_temperature    150(2)
_cell_volume                     1201.70(19)
_computing_cell_refinement       'APEX2 v1.0-22'
_computing_data_collection       'APEX2 v1.0-22 (Bruker, 2004)'
_computing_data_reduction        'APEX2 v1.0-22'
_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_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12557
_diffrn_reflns_theta_full        28.64
_diffrn_reflns_theta_max         28.64
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.897
_exptl_absorpt_correction_T_max  0.8698
_exptl_absorpt_correction_T_min  0.8135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0336
_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)+(0.1000P)²+0.2300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1218
_reflns_number_gt                2611
_reflns_number_total             3097
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om9004753_si_001.cif
_cod_data_source_block           complex5
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4069883
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.5000 0.0000 0.02022(13) Uani 1 2 d S . 1
N1 N 0.53994(13) 0.60740(9) 0.16246(18) 0.0231(3) Uani 1 1 d . A 1
N5 N 0.34761(14) 0.46394(10) 0.14611(19) 0.0259(3) Uani 1 1 d . B 1
N3 N 0.63765(14) 0.42996(9) 0.16908(19) 0.0247(3) Uani 1 1 d . C 1
N2 N 0.66450(14) 0.63605(10) 0.2097(2) 0.0304(3) Uani 1 1 d . A 1
H4 H 0.7341 0.6134 0.1747 0.036 Uiso 1 1 calc R A 1
N4 N 0.74809(16) 0.39011(11) 0.1303(2) 0.0351(4) Uani 1 1 d . C 1
H8 H 0.7748 0.3921 0.0296 0.042 Uiso 1 1 calc R C 1
C7 C 0.26497(18) 0.44702(11) 0.2263(2) 0.0285(4) Uani 1 1 d . B 1
C1 C 0.46311(18) 0.65950(12) 0.2440(2) 0.0309(4) Uani 1 1 d . A 1
H1 H 0.3709 0.6553 0.2359 0.037 Uiso 1 1 calc R A 1
C3 C 0.6677(2) 0.70444(12) 0.3182(3) 0.0341(4) Uani 1 1 d . A 1
H3 H 0.7429 0.7344 0.3669 0.041 Uiso 1 1 calc R A 1
C2 C 0.5393(2) 0.72113(13) 0.3429(3) 0.0364(4) Uani 1 1 d . A 1
H2 H 0.5089 0.7645 0.4114 0.044 Uiso 1 1 calc R A 1
C6 C 0.8128(2) 0.34656(14) 0.2658(3) 0.0412(5) Uani 1 1 d . C 1
H7 H 0.8913 0.3151 0.2668 0.049 Uiso 1 1 calc R C 1
C8 C 0.1589(2) 0.42602(17) 0.3306(3) 0.0485(6) Uani 1 1 d . B 1
H10 H 0.1801 0.4499 0.4448 0.073 Uiso 1 1 calc R B 1
H11 H 0.1505 0.3641 0.3385 0.073 Uiso 1 1 calc R B 1
H9 H 0.0765 0.4502 0.2772 0.073 Uiso 1 1 calc R B 1
C5 C 0.7414(2) 0.35758(15) 0.3995(3) 0.0456(5) Uani 1 1 d . C 1
H6 H 0.7601 0.3350 0.5109 0.055 Uiso 1 1 calc R C 1
C4 C 0.6339(2) 0.40983(15) 0.3362(3) 0.0406(5) Uani 1 1 d . C 1
H5 H 0.5681 0.4283 0.4015 0.049 Uiso 1 1 calc R C 1
B1 B 0.0099(2) 0.36533(16) 0.8296(4) 0.0396(5) Uani 1 1 d . D 1
F1 F -0.12476(12) 0.38020(10) 0.82799(18) 0.0484(3) Uani 1 1 d . D 1
F3 F 0.0831(6) 0.4375(4) 0.8093(12) 0.093(3) Uani 0.602(10) 1 d P D 1
F2 F 0.0317(4) 0.3043(4) 0.7196(10) 0.101(3) Uani 0.602(10) 1 d P D 1
F4 F 0.0492(5) 0.3351(6) 0.9969(8) 0.123(3) Uani 0.602(10) 1 d P D 1
F5 F 0.0632(4) 0.2895(3) 0.8866(10) 0.061(2) Uani 0.398(10) 1 d P D 2
F6 F 0.0234(5) 0.3652(9) 0.6497(6) 0.093(3) Uani 0.398(10) 1 d P D 2
F7 F 0.0795(9) 0.4310(6) 0.8923(14) 0.078(3) Uani 0.398(10) 1 d P D 2
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'
B B 0.0013 0.0007 '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'
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
N1 Ni1 N1 180.0 3_665 .
N1 Ni1 N3 87.96(5) 3_665 3_665
N1 Ni1 N3 92.04(5) . 3_665
N1 Ni1 N3 92.04(5) 3_665 .
N1 Ni1 N3 87.96(5) . .
N3 Ni1 N3 180.0 3_665 .
N1 Ni1 N5 90.99(6) 3_665 .
N1 Ni1 N5 89.01(6) . .
N3 Ni1 N5 89.97(6) 3_665 .
N3 Ni1 N5 90.03(6) . .
N1 Ni1 N5 89.01(6) 3_665 3_665
N1 Ni1 N5 90.99(6) . 3_665
N3 Ni1 N5 90.03(6) 3_665 3_665
N3 Ni1 N5 89.97(6) . 3_665
N5 Ni1 N5 180.0 . 3_665
C1 N1 N2 104.81(14) . .
C1 N1 Ni1 133.15(12) . .
N2 N1 Ni1 122.02(11) . .
C7 N5 Ni1 177.94(15) . .
C4 N3 N4 103.62(15) . .
C4 N3 Ni1 129.17(13) . .
N4 N3 Ni1 127.11(12) . .
N1 N2 C3 112.14(15) . .
N3 N4 C6 112.96(17) . .
N5 C7 C8 179.4(2) . .
N1 C1 C2 110.93(16) . .
N2 C3 C2 106.66(16) . .
C3 C2 C1 105.46(16) . .
C5 C6 N4 106.56(18) . .
C6 C5 C4 105.66(19) . .
N3 C4 C5 111.19(19) . .
F2 B1 F3 112.0(4) . .
F2 B1 F1 111.1(3) . .
F3 B1 F1 114.6(3) . .
F2 B1 F4 108.5(5) . .
F3 B1 F4 106.6(4) . .
F1 B1 F4 103.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 2.0894(14) 3_665
Ni1 N1 2.0895(14) .
Ni1 N3 2.0923(14) 3_665
Ni1 N3 2.0924(14) .
Ni1 N5 2.0996(14) .
Ni1 N5 2.0996(14) 3_665
N1 C1 1.331(2) .
N1 N2 1.3432(19) .
N5 C7 1.133(2) .
N3 C4 1.341(3) .
N3 N4 1.341(2) .
N2 C3 1.347(2) .
N4 C6 1.348(3) .
C7 C8 1.459(3) .
C1 C2 1.393(3) .
C3 C2 1.360(3) .
C6 C5 1.347(3) .
C5 C4 1.393(3) .
B1 F2 1.308(4) .
B1 F3 1.356(6) .
B1 F1 1.380(2) .
B1 F4 1.392(5) .
