#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/18/2221867.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221867
loop_
_publ_author_name
'Guan, Dexin'
'Sun, Hongjian'
_publ_section_title
Bis[4-methyl-2-(4-methylphenyldiazenyl)phenolato-κ²N,O]nickel(II)
_journal_coeditor_code           XU2508
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m566
_journal_paper_doi               10.1107/S1600536809013920
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Ni (C14 H13 N2 O)2]'
_chemical_formula_moiety         'C28 H26 N4 Ni O2'
_chemical_formula_sum            'C28 H26 N4 Ni O2'
_chemical_formula_weight         509.24
_chemical_name_systematic
;
Bis[4-methyl-2-(4-methylphenyldiazenyl)phenolato-
κ²N,O]nickel(II)
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 105.367(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5211(10)
_cell_length_b                   10.8162(11)
_cell_length_c                   12.2647(13)
_cell_measurement_reflns_used    1666
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.42
_cell_measurement_theta_min      2.55
_cell_volume                     1217.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7063
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0378
_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)+(0.0451P)²+0.1292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                1890
_reflns_number_total             2775
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2508.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221867
_cod_database_fobs_code          2221867
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 1.0000 1.0000 0.0000 0.04172(15) Uani d S 1 . .
N N1 0.96662(19) 0.83618(16) 0.04286(15) 0.0412(4) Uani d . 1 . .
N N2 1.02859(19) 0.77982(17) 0.13462(15) 0.0448(5) Uani d . 1 . .
O O 1.0688(2) 1.04670(16) 0.14634(14) 0.0552(5) Uani d . 1 . .
C C7 1.1204(2) 0.8429(2) 0.22272(18) 0.0428(5) Uani d . 1 . .
C C1 0.8685(2) 0.75494(19) -0.03615(18) 0.0402(5) Uani d . 1 . .
C C6 0.9169(3) 0.6442(2) -0.0673(2) 0.0440(5) Uani d . 1 . .
C C4 0.6804(3) 0.6040(2) -0.1919(2) 0.0474(6) Uani d . 1 . .
C C5 0.8231(3) 0.5700(2) -0.1455(2) 0.0480(6) Uani d . 1 . .
C C2 0.7255(3) 0.7908(2) -0.0813(2) 0.0527(6) Uani d . 1 . .
C C12 1.1914(3) 0.7700(3) 0.3162(2) 0.0524(6) Uani d . 1 . .
C C8 1.1345(3) 0.9729(2) 0.2279(2) 0.0462(6) Uani d . 1 . .
C C3 0.6333(3) 0.7146(2) -0.1575(2) 0.0559(7) Uani d . 1 . .
C C9 1.2225(3) 1.0238(3) 0.3292(2) 0.0571(7) Uani d . 1 . .
C C11 1.2798(3) 0.8206(3) 0.4119(2) 0.0560(7) Uani d . 1 . .
C C10 1.2937(3) 0.9492(3) 0.4156(2) 0.0595(7) Uani d . 1 . .
C C13 0.5765(5) 0.5215(4) -0.2756(4) 0.0741(10) Uani d . 1 . .
C C14 1.3546(5) 0.7421(5) 0.5127(3) 0.0827(11) Uani d . 1 . .
H H10 1.347(3) 0.987(2) 0.479(2) 0.050(7) Uiso d . 1 . .
H H5 0.862(3) 0.494(2) -0.165(2) 0.048(7) Uiso d . 1 . .
H H6 1.014(2) 0.624(2) -0.0350(18) 0.047(6) Uiso d . 1 . .
H H12 1.173(3) 0.686(2) 0.311(2) 0.061(8) Uiso d . 1 . .
H H3 0.541(3) 0.737(2) -0.185(2) 0.066(8) Uiso d . 1 . .
H H9 1.232(3) 1.111(3) 0.333(2) 0.066(8) Uiso d . 1 . .
H H13B 0.594(4) 0.440(4) -0.253(3) 0.127(16) Uiso d . 1 . .
H H13A 0.603(5) 0.522(4) -0.338(4) 0.127(19) Uiso d . 1 . .
H H2 0.689(3) 0.867(3) -0.057(2) 0.076(8) Uiso d . 1 . .
H H13C 0.491(5) 0.541(3) -0.290(3) 0.106(15) Uiso d . 1 . .
H H14C 1.454(4) 0.752(4) 0.527(3) 0.111(13) Uiso d . 1 . .
H H14A 1.318(4) 0.761(4) 0.576(3) 0.119(14) Uiso d . 1 . .
H H14B 1.341(5) 0.663(5) 0.504(4) 0.16(2) Uiso d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O Ni O 3_775 . 180.0000(10) ?
O Ni N1 3_775 . 88.33(8) ?
O Ni N1 . . 91.67(8) ?
O Ni N1 3_775 3_775 91.67(8) ?
O Ni N1 . 3_775 88.33(8) ?
N1 Ni N1 . 3_775 180.0 ?
N2 N1 C1 . . 111.38(17) ?
N2 N1 Ni . . 128.07(14) ?
C1 N1 Ni . . 120.38(13) ?
N1 N2 C7 . . 120.24(19) ?
C8 O Ni . . 124.29(15) ?
N2 C7 C12 . . 115.5(2) ?
N2 C7 C8 . . 124.1(2) ?
C12 C7 C8 . . 120.1(2) ?
C6 C1 C2 . . 120.0(2) ?
C6 C1 N1 . . 120.67(19) ?
C2 C1 N1 . . 119.3(2) ?
C1 C6 C5 . . 119.8(2) ?
C1 C6 H6 . . 117.3(15) ?
C5 C6 H6 . . 122.9(15) ?
C5 C4 C3 . . 118.0(2) ?
C5 C4 C13 . . 121.3(3) ?
C3 C4 C13 . . 120.8(3) ?
C4 C5 C6 . . 121.2(2) ?
C4 C5 H5 . . 121.9(15) ?
C6 C5 H5 . . 116.9(15) ?
C3 C2 C1 . . 119.2(2) ?
C3 C2 H2 . . 120.0(15) ?
C1 C2 H2 . . 120.8(15) ?
C11 C12 C7 . . 122.0(3) ?
C11 C12 H12 . . 121.2(16) ?
C7 C12 H12 . . 116.8(16) ?
O C8 C7 . . 123.7(2) ?
O C8 C9 . . 119.2(2) ?
C7 C8 C9 . . 117.0(2) ?
C2 C3 C4 . . 121.8(2) ?
C2 C3 H3 . . 119.1(17) ?
C4 C3 H3 . . 119.2(17) ?
C10 C9 C8 . . 120.7(3) ?
C10 C9 H9 . . 122.2(16) ?
C8 C9 H9 . . 117.0(16) ?
C12 C11 C10 . . 117.3(2) ?
C12 C11 C14 . . 121.8(3) ?
C10 C11 C14 . . 120.8(3) ?
C9 C10 C11 . . 122.8(3) ?
C9 C10 H10 . . 117.0(15) ?
C11 C10 H10 . . 120.2(14) ?
C4 C13 H13B . . 109(2) ?
C4 C13 H13A . . 108(3) ?
H13B C13 H13A . . 101(3) ?
C4 C13 H13C . . 115(3) ?
H13B C13 H13C . . 114(3) ?
H13A C13 H13C . . 108(4) ?
C11 C14 H14C . . 109(2) ?
C11 C14 H14A . . 111(2) ?
H14C C14 H14A . . 113(3) ?
C11 C14 H14B . . 115(3) ?
H14C C14 H14B . . 104(4) ?
H14A C14 H14B . . 104(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni O 3_775 1.8118(16) ?
Ni O . 1.8118(16) y
Ni N1 . 1.8988(18) y
Ni N1 3_775 1.8988(18) ?
N1 N2 . 1.278(2) ?
N1 C1 . 1.451(3) ?
N2 C7 . 1.377(3) ?
O C8 . 1.303(3) ?
C7 C12 . 1.408(3) ?
C7 C8 . 1.412(3) ?
C1 C6 . 1.373(3) ?
C1 C2 . 1.382(3) ?
C6 C5 . 1.381(3) ?
C6 H6 . 0.93(2) ?
C4 C5 . 1.377(3) ?
C4 C3 . 1.382(3) ?
C4 C13 . 1.514(4) ?
C5 H5 . 0.95(2) ?
C2 C3 . 1.374(3) ?
C2 H2 . 0.98(3) ?
C12 C11 . 1.364(3) ?
C12 H12 . 0.92(2) ?
C8 C9 . 1.413(3) ?
C3 H3 . 0.89(2) ?
C9 C10 . 1.361(4) ?
C9 H9 . 0.95(3) ?
C11 C10 . 1.397(4) ?
C11 C14 . 1.513(4) ?
C10 H10 . 0.91(3) ?
C13 H13B . 0.92(4) ?
C13 H13A . 0.87(5) ?
C13 H13C . 0.81(4) ?
C14 H14C . 0.92(4) ?
C14 H14A . 0.95(4) ?
C14 H14B . 0.86(5) ?
