#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/97/2229752.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_2229752
loop_
_publ_author_name
'Wang, Quanbo'
'Jiang, Jianzhuang'
'Zhu, Peihua'
_publ_section_title
;
 Bis{1-[(4-methylphenyl)iminomethyl]-2-naphtholato-κ²N,O}nickel(II)
;
_journal_coeditor_code           LH5218
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m470
_journal_paper_doi               10.1107/S1600536811010087
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Ni (C18 H14 N O)2]'
_chemical_formula_moiety         'C36 H28 N2 Ni O2'
_chemical_formula_sum            'C36 H28 N2 Ni O2'
_chemical_formula_weight         579.31
_chemical_name_systematic
;
Bis{1-[(4-methylphenyl)iminomethyl]-2-naphtholato-
κ²N,O}nickel(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                103.057(4)
_cell_angle_beta                 96.327(4)
_cell_angle_gamma                103.488(4)
_cell_formula_units_Z            1
_cell_length_a                   7.1159(4)
_cell_length_b                   9.9950(5)
_cell_length_c                   10.5803(5)
_cell_measurement_reflns_used    4766
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7557
_cell_measurement_theta_min      3.1849
_cell_volume                     702.21(7)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0355
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6948
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.84809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0286
_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)+(0.0426P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0736
_reflns_number_gt                2438
_reflns_number_total             2753
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5218.cif
_cod_data_source_block           I
_cod_original_cell_volume        702.21(6)
_cod_database_code               2229752
_cod_database_fobs_code          2229752
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 Ni1 1.0000 0.0000 0.0000 0.03301(12) Uani d S 1 . .
O O1 1.13942(16) -0.07866(13) 0.10420(11) 0.0407(3) Uani d . 1 . .
N N1 0.86165(19) 0.06039(14) 0.13584(13) 0.0333(3) Uani d . 1 . .
C C1 0.7670(2) 0.17310(17) 0.13529(15) 0.0330(4) Uani d . 1 . .
C C2 0.5687(2) 0.14945(18) 0.13814(16) 0.0389(4) Uani d . 1 . .
H H2 0.4929 0.0588 0.1347 0.047 Uiso calc R 1 . .
C C3 0.4832(3) 0.26138(19) 0.14616(17) 0.0442(4) Uani d . 1 . .
H H3 0.3494 0.2446 0.1477 0.053 Uiso calc R 1 . .
C C4 0.5911(3) 0.39724(19) 0.15200(17) 0.0436(4) Uani d . 1 . .
C C5 0.7878(3) 0.41810(19) 0.14396(18) 0.0479(5) Uani d . 1 . .
H H5 0.8627 0.5082 0.1452 0.057 Uiso calc R 1 . .
C C6 0.8752(3) 0.30679(19) 0.13413(18) 0.0435(4) Uani d . 1 . .
H H6 1.0071 0.3221 0.1267 0.052 Uiso calc R 1 . .
C C7 0.4985(3) 0.5211(2) 0.1706(2) 0.0656(6) Uani d . 1 . .
H H7A 0.3635 0.4877 0.1285 0.098 Uiso calc R 1 . .
H H7C 0.5673 0.5921 0.1321 0.098 Uiso calc R 1 . .
H H7B 0.5062 0.5619 0.2629 0.098 Uiso calc R 1 . .
C C8 0.8407(2) 0.00365(18) 0.23459(16) 0.0362(4) Uani d . 1 . .
H H8 0.7570 0.0334 0.2897 0.043 Uiso calc R 1 . .
C C9 0.9333(2) -0.09941(17) 0.26675(15) 0.0348(4) Uani d . 1 . .
C C10 0.8838(3) -0.16148(18) 0.37372(16) 0.0378(4) Uani d . 1 . .
C C11 0.7251(3) -0.1453(2) 0.43815(17) 0.0472(5) Uani d . 1 . .
H H11 0.6482 -0.0889 0.4136 0.057 Uiso calc R 1 . .
C C12 0.6802(3) -0.2103(2) 0.53611(18) 0.0582(5) Uani d . 1 . .
H H12 0.5739 -0.1976 0.5768 0.070 Uiso calc R 1 . .
C C13 0.7941(3) -0.2955(2) 0.57493(19) 0.0631(6) Uani d . 1 . .
H H13 0.7626 -0.3406 0.6406 0.076 Uiso calc R 1 . .
C C14 0.9498(3) -0.3120(2) 0.51683(19) 0.0562(5) Uani d . 1 . .
H H14 1.0257 -0.3677 0.5442 0.067 Uiso calc R 1 . .
C C15 1.0000(3) -0.24677(19) 0.41566(17) 0.0436(4) Uani d . 1 . .
C C16 1.1607(3) -0.2661(2) 0.35237(19) 0.0494(5) Uani d . 1 . .
H H16 1.2390 -0.3194 0.3817 0.059 Uiso calc R 1 . .
C C17 1.2044(3) -0.2103(2) 0.25140(18) 0.0454(4) Uani d . 1 . .
H H17 1.3110 -0.2259 0.2125 0.054 Uiso calc R 1 . .
C C18 1.0881(2) -0.12706(17) 0.20317(16) 0.0359(4) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 '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'
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
O1 Ni1 O1 2_755 . 180 ?
O1 Ni1 N1 2_755 . 88.02(5) ?
O1 Ni1 N1 . . 91.98(5) ?
O1 Ni1 N1 2_755 2_755 91.98(5) ?
O1 Ni1 N1 . 2_755 88.02(5) ?
O1 C18 C9 . . 124.55(14) ?
O1 C18 C17 . . 116.56(14) ?
N1 Ni1 N1 . 2_755 180 ?
N1 C8 H8 . . 116.7 ?
N1 C8 C9 . . 126.64(14) ?
C1 N1 Ni1 . . 121.52(10) ?
C1 C2 H2 . . 120.2 ?
C1 C2 C3 . . 119.58(16) ?
C1 C6 C5 . . 120.18(16) ?
C1 C6 H6 . . 119.9 ?
C2 C1 N1 . . 120.54(15) ?
C2 C1 C6 . . 119.37(14) ?
C2 C3 H3 . . 119.1 ?
C3 C2 H2 . . 120.2 ?
C3 C4 C5 . . 117.94(15) ?
C3 C4 C7 . . 121.20(17) ?
C4 C3 C2 . . 121.79(16) ?
C4 C3 H3 . . 119.1 ?
C4 C5 H5 . . 119.5 ?
C4 C5 C6 . . 121.00(17) ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7C . . 109.5 ?
C4 C7 H7B . . 109.5 ?
C5 C4 C7 . . 120.84(18) ?
C5 C6 H6 . . 119.9 ?
C6 C1 N1 . . 120.08(14) ?
C6 C5 H5 . . 119.5 ?
H7A C7 H7C . . 109.5 ?
H7A C7 H7B . . 109.5 ?
H7C C7 H7B . . 109.5 ?
C8 N1 Ni1 . . 123.82(10) ?
C8 N1 C1 . . 114.66(13) ?
C8 C9 C10 . . 120.43(14) ?
C9 C8 H8 . . 116.7 ?
C9 C18 C17 . . 118.85(15) ?
C10 C11 H11 . . 119.0 ?
C11 C10 C9 . . 124.15(15) ?
C11 C10 C15 . . 117.29(16) ?
C11 C12 H12 . . 120.0 ?
C11 C12 C13 . . 120.04(19) ?
C12 C11 C10 . . 122.01(17) ?
C12 C11 H11 . . 119.0 ?
C12 C13 H13 . . 120.1 ?
C13 C12 H12 . . 120.0 ?
C13 C14 H14 . . 119.2 ?
C13 C14 C15 . . 121.60(18) ?
C14 C13 C12 . . 119.80(19) ?
C14 C13 H13 . . 120.1 ?
C14 C15 C10 . . 119.25(17) ?
C14 C15 C16 . . 121.88(16) ?
C15 C10 C9 . . 118.55(15) ?
C15 C14 H14 . . 119.2 ?
C15 C16 H16 . . 118.8 ?
C16 C15 C10 . . 118.86(16) ?
C16 C17 H17 . . 119.7 ?
C16 C17 C18 . . 120.68(16) ?
C17 C16 C15 . . 122.48(15) ?
C17 C16 H16 . . 118.8 ?
C18 O1 Ni1 . . 127.72(10) ?
C18 C9 C8 . . 118.71(15) ?
C18 C9 C10 . . 120.46(14) ?
C18 C17 H17 . . 119.7 ?
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
Ni1 O1 2_755 1.8255(11) ?
Ni1 O1 . 1.8255(11) ?
Ni1 N1 . 1.8964(13) ?
Ni1 N1 2_755 1.8964(13) ?
O1 C18 . 1.302(2) ?
N1 C1 . 1.4420(18) ?
N1 C8 . 1.303(2) ?
C1 C2 . 1.380(2) ?
C1 C6 . 1.381(2) ?
C2 H2 . 0.9300 ?
C2 C3 . 1.383(2) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.379(3) ?
C4 C5 . 1.381(3) ?
C4 C7 . 1.518(2) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.386(2) ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7C . 0.9600 ?
C7 H7B . 0.9600 ?
C8 H8 . 0.9300 ?
C8 C9 . 1.427(2) ?
C9 C10 . 1.447(2) ?
C9 C18 . 1.402(2) ?
C10 C11 . 1.404(2) ?
C10 C15 . 1.423(2) ?
C11 H11 . 0.9300 ?
C11 C12 . 1.370(3) ?
C12 H12 . 0.9300 ?
C12 C13 . 1.399(3) ?
C13 H13 . 0.9300 ?
C13 C14 . 1.350(3) ?
C14 H14 . 0.9300 ?
C14 C15 . 1.410(3) ?
C15 C16 . 1.416(3) ?
C16 H16 . 0.9300 ?
C16 C17 . 1.345(3) ?
C17 H17 . 0.9300 ?
C17 C18 . 1.434(2) ?
