#------------------------------------------------------------------------------
#$Date: 2017-03-30 11:54:21 +0300 (Thu, 30 Mar 2017) $
#$Revision: 194617 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/21/4102198.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_4102198
loop_
_publ_author_name
'Deguang Huang'
'R. H. Holm'
_publ_section_title
;
 Reactions of the Terminal NiII-OH Group in Substitution and Electrophilic
 Reactions with Carbon Dioxide and Other Substrates: Structural Definition
 of Binding Modes in an Intramolecular NiII...FeII Bridged Site
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4693
_journal_page_last               4701
_journal_paper_doi               10.1021/ja1003125
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C24 H21 N4 Ni O2, C8 H20 N'
_chemical_formula_sum            'C32 H41 N5 Ni O2'
_chemical_formula_weight         586.41
_chemical_name_common            (Et4N)[Ni(PyN2(Me2))CN]
_space_group_IT_number           44
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'I 2 -2'
_symmetry_space_group_name_H-M   'I m m 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
SHELXL-97

The cation Et4N+ was treated as disordered model (50/50) and all the
atoms of it was anisotroped in the following refinement.

Hydrogen atoms was not added to Et4N+ due to its high symmetry
and disordered atoms on its ethylene chain, but these hydrogen atoms were
included in the reported formula.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.572(5)
_cell_length_b                   9.016(3)
_cell_length_c                   10.919(4)
_cell_measurement_reflns_used    3677
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.28
_cell_volume                     1533.0(9)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9363
_diffrn_reflns_theta_full        25.86
_diffrn_reflns_theta_max         25.86
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  0.9181
_exptl_absorpt_correction_T_min  0.8948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            light-red
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1629
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0383
_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)+(0.0714P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                1594
_reflns_number_total             1629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1003125_si_006.cif
_cod_data_source_block           Compound7
_cod_depositor_comments
;
 Appending the value of the _chemical_name_systematic data item to the
 value of the _audit_creation_method data item since it contained a
 description of the structure solution proccess and not the systematic
 name of the compound. The _chemical_name_systematic data item was removed.

 Antanas Vaitkus,
 2017-03-30

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     I2-2
_cod_database_code               4102198
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x, -y, z'
'-x, y, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-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 0.0000 0.0000 0.385950(6) 0.0212(2) Uani 1 4 d S
O1 O 0.22275(18) 0.0000 0.2103(3) 0.0275(6) Uani 1 2 d S
N1 N 0.1206(2) 0.0000 0.3637(3) 0.0243(8) Uani 1 2 d S
N2 N 0.0000 0.0000 0.2187(5) 0.0240(13) Uani 1 4 d S
N3 N 0.0000 0.0000 0.6604(5) 0.0332(11) Uani 1 4 d S
C1 C 0.1484(3) 0.0000 0.2480(4) 0.0227(8) Uani 1 2 d S
C2 C 0.0749(2) 0.0000 0.1608(4) 0.0216(8) Uani 1 2 d S
C3 C 0.0770(2) 0.0000 0.0340(4) 0.0258(8) Uani 1 2 d S
H3A H 0.1302 0.0000 -0.0086 0.031 Uiso 1 2 calc SR
C4 C 0.0000 0.0000 -0.0294(6) 0.0281(12) Uani 1 4 d S
H4A H 0.0000 0.0000 -0.1164 0.034 Uiso 1 4 calc SR
C5 C 0.1840(3) 0.0000 0.4565(4) 0.0250(8) Uani 1 2 d S
C6 C 0.21398(19) 0.1331(3) 0.5031(3) 0.0296(7) Uani 1 1 d .
C7 C 0.2742(2) 0.1311(3) 0.5952(3) 0.0350(8) Uani 1 1 d .
H7A H 0.2944 0.2221 0.6281 0.042 Uiso 1 1 calc R
C8 C 0.3054(3) 0.0000 0.6404(4) 0.0349(10) Uani 1 2 d S
H8A H 0.3482 0.0000 0.7024 0.042 Uiso 1 2 calc SR
C9 C 0.1793(2) 0.2773(3) 0.4552(3) 0.0413(8) Uani 1 1 d .
H9A H 0.2073 0.3599 0.4976 0.062 Uiso 1 1 calc R
H9B H 0.1172 0.2816 0.4697 0.062 Uiso 1 1 calc R
H9C H 0.1906 0.2844 0.3671 0.062 Uiso 1 1 calc R
C10 C 0.0000 0.0000 0.5553(6) 0.0250(15) Uani 1 4 d S
N4 N 0.5000 0.0000 0.2916(5) 0.0257(10) Uani 1 4 d S
C11 C 0.4452(3) 0.0931(6) 0.3756(9) 0.0325(12) Uani 0.50 1 d P
C11' C 0.4461(4) 0.0955(7) 0.2079(6) 0.0348(14) Uani 0.50 1 d P
C12 C 0.3884(2) 0.2048(3) 0.2906(5) 0.0461(8) Uani 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'
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
N2 Ni1 C10 180.000(1) . .
N2 Ni1 N1 82.65(10) . .
C10 Ni1 N1 97.35(10) . .
N2 Ni1 N1 82.65(10) . 2
C10 Ni1 N1 97.35(10) . 2
N1 Ni1 N1 165.3(2) . 2
C1 N1 C5 116.9(4) . .
C1 N1 Ni1 116.2(3) . .
C5 N1 Ni1 126.9(3) . .
C2 N2 C2 123.1(6) 2 .
C2 N2 Ni1 118.5(3) 2 .
C2 N2 Ni1 118.5(3) . .
O1 C1 N1 128.5(4) . .
O1 C1 C2 120.6(4) . .
N1 C1 C2 110.9(3) . .
N2 C2 C3 119.8(4) . .
N2 C2 C1 111.8(4) . .
C3 C2 C1 128.4(3) . .
C2 C3 C4 118.6(4) . .
C2 C3 H3A 120.7 . .
C4 C3 H3A 120.7 . .
C3 C4 C3 120.0(6) 2 .
C3 C4 H4A 120.0 2 .
C3 C4 H4A 120.0 . .
C6 C5 C6 120.2(4) . 3
C6 C5 N1 119.89(18) . .
C6 C5 N1 119.89(18) 3 .
C7 C6 C5 119.1(3) . .
C7 C6 C9 120.8(3) . .
C5 C6 C9 120.1(3) . .
C8 C7 C6 121.1(3) . .
C8 C7 H7A 119.4 . .
C6 C7 H7A 119.4 . .
C7 C8 C7 119.2(4) 3 .
C7 C8 H8A 120.4 3 .
C7 C8 H8A 120.4 . .
C6 C9 H9A 109.5 . .
C6 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C6 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N3 C10 Ni1 180.000(1) . .
C11 N4 C11 68.9(5) 4_655 .
C11 N4 C11 105.1(7) 4_655 3
C11 N4 C11 67.6(5) . 3
C11 N4 C11 67.6(5) 4_655 2_655
C11 N4 C11 105.1(7) . 2_655
C11 N4 C11 68.9(5) 3 2_655
C11 N4 C11' 111.8(3) 4_655 2_655
C11 N4 C11' 179.0(4) . 2_655
C11 N4 C11' 111.4(3) 3 2_655
C11 N4 C11' 74.7(4) 2_655 2_655
C11 N4 C11' 179.0(4) 4_655 3
C11 N4 C11' 111.8(3) . 3
C11 N4 C11' 74.7(4) 3 3
C11 N4 C11' 111.4(3) 2_655 3
C11' N4 C11' 67.6(5) 2_655 3
C11 N4 C11' 111.4(3) 4_655 .
C11 N4 C11' 74.7(4) . .
C11 N4 C11' 111.8(3) 3 .
C11 N4 C11' 179.0(4) 2_655 .
C11' N4 C11' 105.6(6) 2_655 .
C11' N4 C11' 69.5(5) 3 .
C11 N4 C11' 74.7(4) 4_655 4_655
C11 N4 C11' 111.4(3) . 4_655
C11 N4 C11' 179.0(4) 3 4_655
C11 N4 C11' 111.8(3) 2_655 4_655
C11' N4 C11' 69.5(5) 2_655 4_655
C11' N4 C11' 105.6(6) 3 4_655
C11' N4 C11' 67.6(5) . 4_655
N4 C11 C12 107.7(6) . .
N4 C11' C12 108.7(5) . .
C11' C12 C11 68.8(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N2 1.826(6) .
Ni1 C10 1.849(7) .
Ni1 N1 1.894(3) .
Ni1 N1 1.894(3) 2
O1 C1 1.229(5) .
N1 C1 1.335(5) .
N1 C5 1.414(5) .
N2 C2 1.327(4) 2
N2 C2 1.327(5) .
N3 C10 1.148(9) .
C1 C2 1.489(6) .
C2 C3 1.385(6) .
C3 C4 1.385(5) .
C3 H3A 0.9500 .
C4 C3 1.385(5) 2
C4 H4A 0.9500 .
C5 C6 1.384(3) .
C5 C6 1.384(3) 3
C6 C7 1.375(4) .
C6 C9 1.502(4) .
C7 C8 1.370(4) .
C7 H7A 0.9500 .
C8 C7 1.370(4) 3
C8 H8A 0.9500 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
N4 C11 1.508(8) 4_655
N4 C11 1.508(8) .
N4 C11 1.508(8) 3
N4 C11 1.508(8) 2_655
N4 C11' 1.510(7) 2_655
N4 C11' 1.510(7) 3
N4 C11' 1.510(7) .
N4 C11' 1.510(7) 4_655
C11 C12 1.630(8) .
C11' C12 1.611(8) .
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
N2 Ni1 N1 C1 0.0 . .
C10 Ni1 N1 C1 180.0 . .
N1 Ni1 N1 C1 0.0 2 .
N2 Ni1 N1 C5 180.0 . .
C10 Ni1 N1 C5 0.0 . .
N1 Ni1 N1 C5 180.0 2 .
C10 Ni1 N2 C2 0(100) . 2
N1 Ni1 N2 C2 180.0 . 2
N1 Ni1 N2 C2 0.0 2 2
C10 Ni1 N2 C2 0(95) . .
N1 Ni1 N2 C2 0.0 . .
N1 Ni1 N2 C2 180.0 2 .
C5 N1 C1 O1 0.0 . .
Ni1 N1 C1 O1 180.0 . .
C5 N1 C1 C2 180.0 . .
Ni1 N1 C1 C2 0.0 . .
C2 N2 C2 C3 0.0 2 .
Ni1 N2 C2 C3 180.0 . .
C2 N2 C2 C1 180.0 2 .
Ni1 N2 C2 C1 0.0 . .
O1 C1 C2 N2 180.0 . .
N1 C1 C2 N2 0.0 . .
O1 C1 C2 C3 0.0 . .
N1 C1 C2 C3 180.0 . .
N2 C2 C3 C4 0.0 . .
C1 C2 C3 C4 180.0 . .
C2 C3 C4 C3 0.0 . 2
C1 N1 C5 C6 91.0(3) . .
Ni1 N1 C5 C6 -89.0(3) . .
C1 N1 C5 C6 -91.0(3) . 3
Ni1 N1 C5 C6 89.0(3) . 3
C6 C5 C6 C7 0.5(6) 3 .
N1 C5 C6 C7 178.5(3) . .
C6 C5 C6 C9 -178.0(3) 3 .
N1 C5 C6 C9 0.0(5) . .
C5 C6 C7 C8 0.7(5) . .
C9 C6 C7 C8 179.2(4) . .
C6 C7 C8 C7 -1.8(7) . 3
N2 Ni1 C10 N3 0.0 . .
N1 Ni1 C10 N3 0(100) . .
N1 Ni1 C10 N3 0(100) 2 .
C11 N4 C11 C12 118.1(3) 4_655 .
C11 N4 C11 C12 -124.5(3) 3 .
C11 N4 C11 C12 176.4(4) 2_655 .
C11' N4 C11 C12 -108(31) 2_655 .
C11' N4 C11 C12 -62.6(5) 3 .
C11' N4 C11 C12 -2.6(3) . .
C11' N4 C11 C12 55.2(5) 4_655 .
C11 N4 C11' C12 -56.8(5) 4_655 .
C11 N4 C11' C12 2.7(4) . .
C11 N4 C11' C12 60.4(6) 3 .
C11 N4 C11' C12 -74(31) 2_655 .
C11' N4 C11' C12 -178.3(5) 2_655 .
C11' N4 C11' C12 123.5(3) 3 .
C11' N4 C11' C12 -118.9(3) 4_655 .
N4 C11' C12 C11 -2.5(3) . .
N4 C11 C12 C11' 2.5(3) . .
