#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/69/2216976.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_2216976
loop_
_publ_author_name
'Li, Zong-Xiao'
'Zhang, Xin-Li'
'Pu, Xiao-Hua'
_publ_section_title
Bis[2-(benzyliminomethyl)-4-chlorophenolato-κ²N,O]nickel(II)
_journal_coeditor_code           CI2496
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m202
_journal_page_last               m202
_journal_paper_doi               10.1107/S1600536807054943
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Ni (C14 H11 Cl N O)2]'
_chemical_formula_moiety         'C28 H22 Cl2 N2 Ni O2'
_chemical_formula_sum            'C28 H22 Cl2 N2 Ni O2'
_chemical_formula_weight         548.09
_chemical_name_systematic
;
Bis[2-(benzyliminomethyl)-4-chlorophenolato-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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.529(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.6785(17)
_cell_length_b                   10.5986(14)
_cell_length_c                   8.6560(13)
_cell_measurement_reflns_used    1825
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.231
_cell_measurement_theta_min      2.476
_cell_volume                     1196.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and 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  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5718
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.064
_exptl_absorpt_correction_T_max  0.7270
_exptl_absorpt_correction_T_min  0.5872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombus
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0426
_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)+(0.0570P)²+0.6708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1238
_reflns_number_gt                1506
_reflns_number_total             2110
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2496.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2216976
_cod_database_fobs_code          2216976
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
Ni Ni1 0.0000 0.5000 0.0000 0.0329(2) Uani d S 1
Cl Cl1 0.48272(9) 0.77502(16) 0.44350(18) 0.0919(6) Uani d . 1
N N1 0.0104(2) 0.6504(3) 0.1288(3) 0.0316(7) Uani d . 1
O O1 0.13607(19) 0.4664(3) 0.0829(3) 0.0472(7) Uani d . 1
C C1 0.0949(3) 0.7006(4) 0.2141(4) 0.0354(8) Uani d . 1
H H1 0.0899 0.7737 0.2705 0.043 Uiso calc R 1
C C2 0.1963(3) 0.6549(4) 0.2309(4) 0.0359(9) Uani d . 1
C C3 0.2107(3) 0.5393(4) 0.1629(4) 0.0365(9) Uani d . 1
C C4 0.3123(3) 0.4982(4) 0.1878(5) 0.0467(10) Uani d . 1
H H4 0.3240 0.4208 0.1461 0.056 Uiso calc R 1
C C5 0.3939(3) 0.5699(5) 0.2720(5) 0.0528(11) Uani d . 1
H H5 0.4603 0.5418 0.2855 0.063 Uiso calc R 1
C C6 0.3779(3) 0.6840(5) 0.3372(5) 0.0520(11) Uani d . 1
C C7 0.2809(3) 0.7283(4) 0.3197(5) 0.0451(10) Uani d . 1
H H7 0.2710 0.8048 0.3653 0.054 Uiso calc R 1
C C8 -0.0831(3) 0.7179(4) 0.1351(4) 0.0369(9) Uani d . 1
H H8A -0.1254 0.7353 0.0253 0.044 Uiso calc R 1
H H8B -0.0633 0.7982 0.1893 0.044 Uiso calc R 1
C C9 -0.1461(2) 0.6457(3) 0.2219(4) 0.0316(8) Uani d . 1
C C10 -0.1084(3) 0.5490(4) 0.3262(4) 0.0393(9) Uani d . 1
H H10 -0.0411 0.5225 0.3438 0.047 Uiso calc R 1
C C11 -0.1688(3) 0.4897(4) 0.4064(5) 0.0469(10) Uani d . 1
H H11 -0.1422 0.4233 0.4767 0.056 Uiso calc R 1
C C12 -0.2678(3) 0.5281(4) 0.3827(5) 0.0533(12) Uani d . 1
H H12 -0.3087 0.4878 0.4361 0.064 Uiso calc R 1
C C13 -0.3059(3) 0.6264(5) 0.2799(5) 0.0553(12) Uani d . 1
H H13 -0.3725 0.6544 0.2651 0.066 Uiso calc R 1
C C14 -0.2457(3) 0.6839(4) 0.1983(5) 0.0458(10) Uani d . 1
H H14 -0.2727 0.7493 0.1265 0.055 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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 . 3_565 180 y
O1 Ni1 N1 . 3_565 87.39(11) y
O1 Ni1 N1 3_565 3_565 92.61(11) ?
O1 Ni1 N1 . . 92.61(11) y
O1 Ni1 N1 3_565 . 87.39(11) ?
N1 Ni1 N1 3_565 . 180.00(14) ?
C1 N1 C8 . . 114.6(3) ?
C1 N1 Ni1 . . 124.9(2) ?
C8 N1 Ni1 . . 120.5(2) ?
C3 O1 Ni1 . . 129.8(3) ?
N1 C1 C2 . . 126.4(4) ?
N1 C1 H1 . . 116.8 ?
C2 C1 H1 . . 116.8 ?
C3 C2 C7 . . 120.9(3) ?
C3 C2 C1 . . 120.5(3) ?
C7 C2 C1 . . 118.5(4) ?
O1 C3 C2 . . 123.8(3) ?
O1 C3 C4 . . 118.5(4) ?
C2 C3 C4 . . 117.6(3) ?
C5 C4 C3 . . 121.3(4) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
C4 C5 C6 . . 120.1(4) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C7 C6 C5 . . 121.4(4) ?
C7 C6 Cl1 . . 118.9(4) ?
C5 C6 Cl1 . . 119.6(3) ?
C6 C7 C2 . . 118.6(4) ?
C6 C7 H7 . . 120.7 ?
C2 C7 H7 . . 120.7 ?
N1 C8 C9 . . 113.7(3) ?
N1 C8 H8A . . 108.8 ?
C9 C8 H8A . . 108.8 ?
N1 C8 H8B . . 108.8 ?
C9 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
C10 C9 C14 . . 118.7(3) ?
C10 C9 C8 . . 123.5(3) ?
C14 C9 C8 . . 117.7(3) ?
C9 C10 C11 . . 120.8(3) ?
C9 C10 H10 . . 119.6 ?
C11 C10 H10 . . 119.6 ?
C12 C11 C10 . . 120.3(4) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C13 C12 C11 . . 119.4(4) ?
C13 C12 H12 . . 120.3 ?
C11 C12 H12 . . 120.3 ?
C12 C13 C14 . . 120.1(4) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C9 C14 C13 . . 120.7(4) ?
C9 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
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 . 1.817(2) y
Ni1 O1 3_565 1.817(2) ?
Ni1 N1 3_565 1.926(3) ?
Ni1 N1 . 1.926(3) y
Cl1 C6 . 1.743(4) ?
N1 C1 . 1.284(4) ?
N1 C8 . 1.480(4) ?
O1 C3 . 1.301(4) ?
C1 C2 . 1.434(5) ?
C1 H1 . 0.93 ?
C2 C3 . 1.399(5) ?
C2 C7 . 1.414(5) ?
C3 C4 . 1.409(5) ?
C4 C5 . 1.365(6) ?
C4 H4 . 0.93 ?
C5 C6 . 1.379(6) ?
C5 H5 . 0.93 ?
C6 C7 . 1.372(5) ?
C7 H7 . 0.93 ?
C8 C9 . 1.510(5) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 C10 . 1.361(5) ?
C9 C14 . 1.377(5) ?
C10 C11 . 1.380(5) ?
C10 H10 . 0.93 ?
C11 C12 . 1.369(6) ?
C11 H11 . 0.93 ?
C12 C13 . 1.367(6) ?
C12 H12 . 0.93 ?
C13 C14 . 1.378(6) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
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_site_symmetry_1
_geom_torsion
O1 Ni1 N1 C1 . 9.0(3)
O1 Ni1 N1 C1 3_565 -171.0(3)
O1 Ni1 N1 C8 . -171.1(2)
O1 Ni1 N1 C8 3_565 8.9(2)
N1 Ni1 O1 C3 3_565 164.0(3)
N1 Ni1 O1 C3 . -16.0(3)
C8 N1 C1 C2 . 179.6(3)
Ni1 N1 C1 C2 . -0.4(5)
N1 C1 C2 C3 . -6.1(6)
N1 C1 C2 C7 . 174.9(3)
Ni1 O1 C3 C2 . 14.1(5)
Ni1 O1 C3 C4 . -168.2(3)
C7 C2 C3 O1 . 178.5(3)
C1 C2 C3 O1 . -0.5(5)
C7 C2 C3 C4 . 0.7(5)
C1 C2 C3 C4 . -178.2(3)
O1 C3 C4 C5 . -179.4(4)
C2 C3 C4 C5 . -1.5(6)
C3 C4 C5 C6 . 1.1(6)
C4 C5 C6 C7 . 0.0(7)
C4 C5 C6 Cl1 . -179.7(3)
C5 C6 C7 C2 . -0.8(6)
Cl1 C6 C7 C2 . 178.9(3)
C3 C2 C7 C6 . 0.4(5)
C1 C2 C7 C6 . 179.3(3)
C1 N1 C8 C9 . -111.5(3)
Ni1 N1 C8 C9 . 68.5(3)
N1 C8 C9 C10 . 19.2(5)
N1 C8 C9 C14 . -163.5(3)
C14 C9 C10 C11 . 0.4(6)
C8 C9 C10 C11 . 177.6(4)
C9 C10 C11 C12 . -0.5(6)
C10 C11 C12 C13 . -0.5(6)
C11 C12 C13 C14 . 1.5(7)
C10 C9 C14 C13 . 0.7(6)
C8 C9 C14 C13 . -176.8(4)
C12 C13 C14 C9 . -1.6(7)
