#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/31/2233117.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_2233117
loop_
_publ_author_name
'Wang, Ning'
_publ_section_title
;
 Bis[2-(1-iminoethyl)phenolato-κ²N,O]nickel(II)
;
_journal_coeditor_code           CV5207
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m11
_journal_paper_doi               10.1107/S1600536811051476
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Ni (C8 H8 N O)2]'
_chemical_formula_moiety         'C16 H16 N2 Ni O2'
_chemical_formula_sum            'C16 H16 N2 Ni O2'
_chemical_formula_weight         327.02
_chemical_name_systematic
;
Bis[2-(1-iminoethyl)phenolato-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                101.006(3)
_cell_angle_beta                 93.049(3)
_cell_angle_gamma                109.777(3)
_cell_formula_units_Z            3
_cell_length_a                   9.1084(10)
_cell_length_b                   11.3612(16)
_cell_length_c                   11.8249(18)
_cell_measurement_reflns_used    772
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.3
_cell_volume                     1121.1(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (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      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω 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  0.0444
_diffrn_reflns_av_sigmaI/netI    0.1125
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6121
_diffrn_reflns_theta_full        25.66
_diffrn_reflns_theta_max         25.66
_diffrn_reflns_theta_min         1.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  0.7993
_exptl_absorpt_correction_T_min  0.7806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.386
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4190
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1360
_refine_ls_R_factor_gt           0.0619
_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)+(0.0585P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                2297
_reflns_number_total             4190
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5207.cif
_cod_data_source_block           I
_cod_database_code               2233117
_cod_database_fobs_code          2233117
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_symmetry_multiplicity
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
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
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_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)
