#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:54:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178587 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/98/4069881.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_4069881
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 Cl2 N10 Ni O8'
_chemical_formula_weight         612.05
_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                 96.330(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2512(7)
_cell_length_b                   15.4555(11)
_cell_length_c                   7.8203(6)
_cell_measurement_temperature    150(2)
_cell_volume                     1231.47(15)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12753
_diffrn_reflns_theta_full        28.57
_diffrn_reflns_theta_max         28.57
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_T_max  0.882
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.154
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0526
_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+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1630
_refine_ls_wR_factor_ref         0.1704
_reflns_number_gt                2564
_reflns_number_total             3148
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om9004753_si_001.cif
_cod_data_source_block           complex2
_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               4069881
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
Ni1 Ni 0.0000 1.0000 0.0000 0.02182(18) Uani 1 2 d S
Cl1 Cl 0.51019(7) 0.13216(5) 0.82418(13) 0.0411(2) Uani 1 1 d .
O1 O 0.3735(3) 0.1148(2) 0.8193(4) 0.0538(7) Uani 1 1 d .
O2 O 0.5861(3) 0.0595(2) 0.8189(9) 0.123(2) Uani 1 1 d .
O4 O 0.5291(5) 0.1867(5) 0.6904(10) 0.163(4) Uani 1 1 d .
O3 O 0.5546(6) 0.1799(7) 0.9627(13) 0.225(6) Uani 1 1 d .
N1 N 0.0346(2) 0.89275(15) 0.1616(3) 0.0242(5) Uani 1 1 d .
N2 N 0.1568(3) 0.86403(18) 0.2111(4) 0.0355(6) Uani 1 1 d .
N3 N 0.1372(2) 1.06799(16) 0.1674(3) 0.0270(5) Uani 1 1 d .
N5 N -0.1505(2) 1.03846(16) 0.1455(3) 0.0272(5) Uani 1 1 d .
N4 N 0.2466(3) 1.10698(19) 0.1301(4) 0.0387(7) Uani 1 1 d .
H8 H 0.2737 1.1054 0.0300 0.046 Uiso 1 1 calc R
C7 C -0.2317(3) 1.0563(2) 0.2268(4) 0.0316(6) Uani 1 1 d .
C1 C -0.0434(3) 0.8404(2) 0.2402(4) 0.0335(7) Uani 1 1 d .
H1 H -0.1345 0.8443 0.2304 0.040 Uiso 1 1 calc R
C2 C 0.0302(3) 0.7791(2) 0.3387(5) 0.0373(7) Uani 1 1 d .
H2 H -0.0013 0.7357 0.4056 0.045 Uiso 1 1 calc R
C3 C 0.1567(3) 0.7955(2) 0.3174(5) 0.0363(7) Uani 1 1 d .
H3 H 0.2298 0.7652 0.3667 0.044 Uiso 1 1 calc R
C8 C -0.3355(4) 1.0790(3) 0.3317(6) 0.0525(10) Uani 1 1 d .
H10 H -0.4173 1.0554 0.2807 0.079 Uiso 1 1 calc R
H11 H -0.3425 1.1408 0.3382 0.079 Uiso 1 1 calc R
H9 H -0.3151 1.0558 0.4453 0.079 Uiso 1 1 calc R
C4 C 0.3110(3) 1.1496(2) 0.2664(6) 0.0440(9) Uani 1 1 d .
H7 H 0.3895 1.1798 0.2678 0.053 Uiso 1 1 calc R
C6 C 0.1320(4) 1.0886(3) 0.3349(5) 0.0435(8) Uani 1 1 d .
C5 C 0.2399(4) 1.1395(3) 0.3968(5) 0.0488(9) Uani 1 1 d .
H6 H 0.2581 1.1618 0.5073 0.059 Uiso 1 1 calc R
H4 H 0.218(4) 0.882(3) 0.164(6) 0.041(11) Uiso 1 1 d .
H5 H 0.047(5) 1.070(3) 0.398(7) 0.070(15) Uiso 1 1 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'
Cl Cl 0.1484 0.1585 '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_575 .
N1 Ni1 N3 92.16(9) 3_575 .
N1 Ni1 N3 87.84(10) . .
N1 Ni1 N3 87.84(9) 3_575 3_575
N1 Ni1 N3 92.16(10) . 3_575
N3 Ni1 N3 180.00(11) . 3_575
N1 Ni1 N5 89.01(10) 3_575 3_575
N1 Ni1 N5 90.99(10) . 3_575
N3 Ni1 N5 89.89(10) . 3_575
N3 Ni1 N5 90.11(10) 3_575 3_575
N1 Ni1 N5 90.99(10) 3_575 .
N1 Ni1 N5 89.01(10) . .
N3 Ni1 N5 90.12(10) . .
N3 Ni1 N5 89.88(10) 3_575 .
N5 Ni1 N5 180.0 3_575 .
O3 Cl1 O2 109.3(4) . .
O3 Cl1 O4 102.2(6) . .
O2 Cl1 O4 110.6(4) . .
O3 Cl1 O1 111.7(4) . .
O2 Cl1 O1 113.9(2) . .
O4 Cl1 O1 108.5(3) . .
C1 N1 N2 104.7(2) . .
C1 N1 Ni1 133.5(2) . .
N2 N1 Ni1 121.75(19) . .
N1 N2 C3 111.9(3) . .
N4 N3 C6 103.2(3) . .
N4 N3 Ni1 127.8(2) . .
C6 N3 Ni1 128.8(2) . .
C7 N5 Ni1 177.5(3) . .
N3 N4 C4 113.3(3) . .
N5 C7 C8 179.7(4) . .
N1 C1 C2 110.6(3) . .
C3 C2 C1 105.9(3) . .
N2 C3 C2 106.9(3) . .
C5 C4 N4 106.6(3) . .
N3 C6 C5 110.7(3) . .
C4 C5 C6 106.3(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 2.091(2) 3_575
Ni1 N1 2.091(2) .
Ni1 N3 2.095(3) .
Ni1 N3 2.095(3) 3_575
Ni1 N5 2.101(2) 3_575
Ni1 N5 2.101(2) .
Cl1 O3 1.348(6) .
Cl1 O2 1.370(4) .
Cl1 O4 1.374(5) .
Cl1 O1 1.423(3) .
N1 C1 1.335(4) .
N1 N2 1.344(3) .
N2 C3 1.347(4) .
N3 N4 1.333(4) .
N3 C6 1.355(5) .
N5 C7 1.135(4) .
N4 C4 1.360(5) .
C7 C8 1.456(5) .
C1 C2 1.390(5) .
C2 C3 1.349(5) .
C4 C5 1.326(6) .
C6 C5 1.399(5) .
