##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2011-11-19
_journal_date_accepted     2011-11-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      1
_journal_page_first     m11
_journal_page_last     m11
_journal_paper_category     QM
_journal_paper_doi     10.1107/S1600536811051476
_journal_coeditor_code     CV5207
_publ_contact_author_name     'Ning Wang'
_publ_contact_author_address
;
Department of Chemical Engineering
Henan University of Urban Construction
Pingdingshan 467044
People's Republic of China
;
_publ_contact_author_email     wangning7903@yahoo.com.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Bis[2-(1-iminoethyl)phenolato-κ²N,O]nickel(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Ning Wang'
;
Department of Chemical Engineering
Henan University of Urban Construction
Pingdingshan 467044
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Bis[2-(1-iminoethyl)phenolato-κ²N,O]nickel(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H16 N2 Ni O2'
_chemical_formula_sum     'C16 H16 N2 Ni O2'
_chemical_formula_iupac     '[Ni (C8 H8 N O)2]'
_chemical_formula_weight     327.02
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.1084(10)
_cell_length_b     11.3612(16)
_cell_length_c     11.8249(18)
_cell_angle_alpha     101.006(3)
_cell_angle_beta     93.049(3)
_cell_angle_gamma     109.777(3)
_cell_volume     1121.1(3)
_cell_formula_units_Z     3
_cell_measurement_reflns_used     772
_cell_measurement_theta_min     2.3
_cell_measurement_theta_max     24.5
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.453
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     510
_exptl_absorpt_coefficient_mu     1.303
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min     0.7806
_exptl_absorpt_correction_T_max     0.7993
_exptl_special_details     ?
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6121
_diffrn_reflns_av_R_equivalents     0.0444
_diffrn_reflns_av_sigmaI/netI     0.1125
_diffrn_reflns_theta_min     1.77
_diffrn_reflns_theta_max     25.66
_diffrn_reflns_theta_full     25.66
_diffrn_measured_fraction_theta_max     0.986
_diffrn_measured_fraction_theta_full     0.986
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     4190
_reflns_number_gt     2297
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1360
_refine_ls_R_factor_gt     0.0619
_refine_ls_wR_factor_gt     0.1164
_refine_ls_wR_factor_ref     0.1462
_refine_ls_goodness_of_fit_ref     0.986
_refine_ls_restrained_S_all     0.986
_refine_ls_number_reflns     4190
_refine_ls_number_parameters     298
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0585P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.477
_refine_diff_density_min     -0.386
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Ni Ni1 0.5000 0.5000 0.5000 0.0392(3) Uani d S 1 2 . .
    Ni Ni2 0.35993(9) 0.05065(7) 0.23238(6) 0.0385(3) Uani d . 1 1 . .
    O O1 0.1878(5) -0.0945(3) 0.2135(3) 0.0472(11) Uani d . 1 1 . .
    O O2 0.5346(5) 0.1953(3) 0.2545(3) 0.0473(11) Uani d . 1 1 . .
    O O3 0.4558(5) 0.4475(3) 0.3430(3) 0.0477(11) Uani d . 1 1 . .
    N N1 0.2586(6) 0.1539(4) 0.3058(4) 0.0423(12) Uani d D 1 1 . .
    N N2 0.4618(6) -0.0507(4) 0.1545(4) 0.0423(12) Uani d D 1 1 . .
    N N3 0.4211(6) 0.6312(4) 0.5050(4) 0.0416(12) Uani d D 1 1 . .
    C C1 0.0143(7) -0.0061(6) 0.3199(5) 0.0451(15) Uani d . 1 1 . .
    C C2 0.0540(7) -0.1072(6) 0.2547(5) 0.0445(16) Uani d . 1 1 . .
    C C3 -0.0595(8) -0.2330(6) 0.2351(6) 0.0571(18) Uani d . 1 1 . .
    H H3 -0.0379 -0.3009 0.1913 0.069 Uiso calc R 1 1 . .
    C C4 -0.1993(8) -0.2566(7) 0.2789(6) 0.067(2) Uani d . 1 1 . .
    H H4 -0.2708 -0.3403 0.2651 0.080 Uiso calc R 1 1 . .
    C C5 -0.2365(9) -0.1581(8) 0.3436(6) 0.070(2) Uani d . 1 1 . .
    H H5 -0.3316 -0.1752 0.3741 0.084 Uiso calc R 1 1 . .
    C C6 -0.1317(8) -0.0350(7) 0.3621(6) 0.0594(19) Uani d . 1 1 . .
    H H6 -0.1581 0.0314 0.4039 0.071 Uiso calc R 1 1 . .
    C C7 0.1213(7) 0.1262(6) 0.3398(5) 0.0423(15) Uani d . 1 1 . .
    C C8 0.0716(8) 0.2323(6) 0.4004(6) 0.065(2) Uani d . 1 1 . .
    H H8A 0.1536 0.3133 0.4047 0.098 Uiso calc R 1 1 . .
    H H8B 0.0519 0.2216 0.4775 0.098 Uiso calc R 1 1 . .
    H H8C -0.0226 0.2298 0.3579 0.098 Uiso calc R 1 1 . .
    C C9 0.7050(7) 0.1099(6) 0.1411(5) 0.0419(15) Uani d . 1 1 . .
    C C10 0.6652(7) 0.2101(6) 0.2071(5) 0.0433(15) Uani d . 1 1 . .
    C C11 0.7740(8) 0.3369(6) 0.2241(6) 0.0563(18) Uani d . 1 1 . .
    H H11 0.7512 0.4047 0.2672 0.068 Uiso calc R 1 1 . .
    C C12 0.9132(9) 0.3605(7) 0.1774(6) 0.066(2) Uani d . 1 1 . .
    H H12 0.9839 0.4444 0.1908 0.080 Uiso calc R 1 1 . .
    C C13 0.9520(9) 0.2637(9) 0.1111(7) 0.075(2) Uani d . 1 1 . .
    H H13 1.0458 0.2816 0.0787 0.090 Uiso calc R 1 1 . .
    C C14 0.8479(8) 0.1411(7) 0.0948(6) 0.0613(19) Uani d . 1 1 . .
    H H14 0.8730 0.0752 0.0508 0.074 Uiso calc R 1 1 . .
    C C15 0.5979(7) -0.0231(5) 0.1195(5) 0.0396(15) Uani d . 1 1 . .
    C C16 0.6453(8) -0.1295(6) 0.0558(5) 0.0563(18) Uani d . 1 1 . .
    H H16A 0.5654 -0.2106 0.0551 0.084 Uiso calc R 1 1 . .
    H H16B 0.7430 -0.1254 0.0941 0.084 Uiso calc R 1 1 . .
    H H16C 0.6577 -0.1204 -0.0226 0.084 Uiso calc R 1 1 . .
    C C17 0.3474(6) 0.6042(5) 0.3019(5) 0.0354(14) Uani d . 1 1 . .
    C C18 0.3980(7) 0.4986(5) 0.2679(5) 0.0412(15) Uani d . 1 1 . .
    C C19 0.3859(7) 0.4450(6) 0.1502(5) 0.0491(16) Uani d . 1 1 . .
    H H19 0.4205 0.3770 0.1271 0.059 Uiso calc R 1 1 . .
    C C20 0.3235(8) 0.4911(6) 0.0672(6) 0.0562(18) Uani d . 1 1 . .
    H H20 0.3155 0.4532 -0.0109 0.067 Uiso calc R 1 1 . .
    C C21 0.2730(8) 0.5925(6) 0.0987(6) 0.0567(18) Uani d . 1 1 . .
    H H21 0.2314 0.6234 0.0422 0.068 Uiso calc R 1 1 . .
    C C22 0.2843(7) 0.6477(6) 0.2141(6) 0.0474(16) Uani d . 1 1 . .
    H H22 0.2494 0.7159 0.2348 0.057 Uiso calc R 1 1 . .
    C C23 0.3618(6) 0.6684(5) 0.4228(5) 0.0368(14) Uani d . 1 1 . .
    C C24 0.3106(9) 0.7818(6) 0.4540(5) 0.066(2) Uani d . 1 1 . .
    H H24A 0.3309 0.8143 0.5366 0.099 Uiso calc R 1 1 . .
    H H24B 0.2000 0.7559 0.4291 0.099 Uiso calc R 1 1 . .
    H H24C 0.3680 0.8477 0.4161 0.099 Uiso calc R 1 1 . .
    H H1 0.306(7) 0.2400(13) 0.325(5) 0.080 Uiso d D 1 1 . .
    H H2 0.399(6) -0.134(2) 0.139(5) 0.080 Uiso d D 1 1 . .
    H H3A 0.434(8) 0.676(5) 0.578(2) 0.080 Uiso d D 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 O3 2_666 1.816(4) ?
    Ni1 O3 . 1.816(4) ?
    Ni1 N3 . 1.853(5) ?
    Ni1 N3 2_666 1.853(5) ?
    Ni2 O1 . 1.817(4) ?
    Ni2 O2 . 1.822(4) ?
    Ni2 N1 . 1.847(5) ?
    Ni2 N2 . 1.856(5) ?
    O1 C2 . 1.310(7) ?
    O2 C10 . 1.315(7) ?
    O3 C18 . 1.326(6) ?
    N1 C7 . 1.289(7) ?
    N1 H1 . 0.902(10) ?
    N2 C15 . 1.283(7) ?
    N2 H2 . 0.899(10) ?
    N3 C23 . 1.294(7) ?
    N3 H3A . 0.897(10) ?
    C1 C6 . 1.400(8) ?
    C1 C2 . 1.420(8) ?
    C1 C7 . 1.454(8) ?
    C2 C3 . 1.418(8) ?
    C3 C4 . 1.361(9) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.383(9) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.369(9) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.498(8) ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 C14 . 1.398(8) ?
    C9 C10 . 1.417(8) ?
    C9 C15 . 1.459(8) ?
    C10 C11 . 1.414(8) ?
    C11 C12 . 1.374(9) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.382(10) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.364(9) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.501(7) ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C17 C22 . 1.406(7) ?
    C17 C18 . 1.422(7) ?
    C17 C23 . 1.453(7) ?
    C18 C19 . 1.391(8) ?
    C19 C20 . 1.378(8) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.375(8) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.371(8) ?
    C21 H21 . 0.9300 ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.502(7) ?
    C24 H24A . 0.9600 ?
    C24 H24B . 0.9600 ?
    C24 H24C . 0.9600 ?
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
    O3 Ni1 O3 2_666 . 180.0000(10)
                                 ?
    O3 Ni1 N3 2_666 . 86.81(18) ?
    O3 Ni1 N3 . . 93.19(18) ?
    O3 Ni1 N3 2_666 2_666 93.19(18) ?
    O3 Ni1 N3 . 2_666 86.81(18) ?
    N3 Ni1 N3 . 2_666 180.000(2) ?
    O1 Ni2 O2 . . 178.57(18) ?
    O1 Ni2 N1 . . 93.24(19) ?
    O2 Ni2 N1 . . 87.0(2) ?
    O1 Ni2 N2 . . 87.43(19) ?
    O2 Ni2 N2 . . 92.39(19) ?
    N1 Ni2 N2 . . 178.2(2) ?
    C2 O1 Ni2 . . 127.8(4) ?
    C10 O2 Ni2 . . 127.8(4) ?
    C18 O3 Ni1 . . 129.2(4) ?
    C7 N1 Ni2 . . 131.3(4) ?
    C7 N1 H1 . . 108(4) ?
    Ni2 N1 H1 . . 121(4) ?
    C15 N2 Ni2 . . 132.2(4) ?
    C15 N2 H2 . . 118(4) ?
    Ni2 N2 H2 . . 110(4) ?
    C23 N3 Ni1 . . 131.0(4) ?
    C23 N3 H3A . . 119(4) ?
    Ni1 N3 H3A . . 110(4) ?
    C6 C1 C2 . . 119.1(6) ?
    C6 C1 C7 . . 120.2(6) ?
    C2 C1 C7 . . 120.6(5) ?
    O1 C2 C3 . . 117.3(6) ?
    O1 C2 C1 . . 125.5(5) ?
    C3 C2 C1 . . 117.2(6) ?
    C4 C3 C2 . . 121.7(7) ?
    C4 C3 H3 . . 119.2 ?
    C2 C3 H3 . . 119.2 ?
    C3 C4 C5 . . 121.0(7) ?
    C3 C4 H4 . . 119.5 ?
    C5 C4 H4 . . 119.5 ?
    C6 C5 C4 . . 119.2(7) ?
    C6 C5 H5 . . 120.4 ?
    C4 C5 H5 . . 120.4 ?
    C5 C6 C1 . . 121.9(7) ?
    C5 C6 H6 . . 119.0 ?
    C1 C6 H6 . . 119.0 ?
    N1 C7 C1 . . 121.0(5) ?
    N1 C7 C8 . . 119.3(6) ?
    C1 C7 C8 . . 119.7(6) ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C14 C9 C10 . . 118.7(6) ?
    C14 C9 C15 . . 120.5(6) ?
    C10 C9 C15 . . 120.8(5) ?
    O2 C10 C11 . . 116.8(6) ?
    O2 C10 C9 . . 125.4(5) ?
    C11 C10 C9 . . 117.9(6) ?
    C12 C11 C10 . . 120.3(7) ?
    C12 C11 H11 . . 119.8 ?
    C10 C11 H11 . . 119.8 ?
    C11 C12 C13 . . 122.3(7) ?
    C11 C12 H12 . . 118.9 ?
    C13 C12 H12 . . 118.9 ?
    C14 C13 C12 . . 117.7(7) ?
    C14 C13 H13 . . 121.2 ?
    C12 C13 H13 . . 121.2 ?
    C13 C14 C9 . . 123.1(7) ?
    C13 C14 H14 . . 118.4 ?
    C9 C14 H14 . . 118.4 ?
    N2 C15 C9 . . 120.5(5) ?
    N2 C15 C16 . . 119.1(5) ?
    C9 C15 C16 . . 120.4(5) ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C22 C17 C18 . . 118.0(5) ?
    C22 C17 C23 . . 119.9(5) ?
    C18 C17 C23 . . 122.1(5) ?
    O3 C18 C19 . . 117.8(5) ?
    O3 C18 C17 . . 123.3(5) ?
    C19 C18 C17 . . 118.9(5) ?
    C20 C19 C18 . . 121.1(6) ?
    C20 C19 H19 . . 119.5 ?
    C18 C19 H19 . . 119.5 ?
    C21 C20 C19 . . 120.8(6) ?
    C21 C20 H20 . . 119.6 ?
    C19 C20 H20 . . 119.6 ?
    C22 C21 C20 . . 119.4(6) ?
    C22 C21 H21 . . 120.3 ?
    C20 C21 H21 . . 120.3 ?
    C21 C22 C17 . . 121.9(6) ?
    C21 C22 H22 . . 119.1 ?
    C17 C22 H22 . . 119.1 ?
    N3 C23 C17 . . 121.1(5) ?
    N3 C23 C24 . . 118.8(5) ?
    C17 C23 C24 . . 120.1(5) ?
    C23 C24 H24A . . 109.5 ?
    C23 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C23 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N3 H3A O2 2_666 0.897(10) 2.164(15) 3.055(6) 172(6)
    N1 H1 O3 . 0.902(10) 2.250(18) 3.138(6) 168(6)
    C22 H22 O1 1_565 0.93 2.46 3.332(6) 157(6)
