#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/93/2209310.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_2209310
loop_
_publ_author_name
'Liu, Hui-Yan '
'Gao, Feng'
'Lu, Zai-Sheng'
'Wang, Hai-Ying'
_publ_section_title
Bis[1-(2-hydroxyethyliminomethyl)-2-naphtholato-κ²N,O]nickel(II)
_journal_coeditor_code           SJ2054
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1306
_journal_page_last               m1308
_journal_paper_doi               10.1107/S1600536806017041
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Ni (C13 H12 N1 O2)2]'
_chemical_formula_moiety         'C26 H24 N2 Ni O4'
_chemical_formula_sum            'C26 H24 N2 Ni O4'
_chemical_formula_weight         487.18
_chemical_name_systematic
;
Bis[1-(2-hydroxyethyliminomethyl)-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                105.941(6)
_cell_angle_beta                 109.636(6)
_cell_angle_gamma                103.438(6)
_cell_formula_units_Z            2
_cell_length_a                   10.227(4)
_cell_length_b                   10.288(4)
_cell_length_c                   12.119(5)
_cell_measurement_reflns_used    1179
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.892
_cell_measurement_theta_min      2.264
_cell_volume                     1078.0(7)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker CCD area-detector'
_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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0882
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5658
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_T_max  0.9373
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0522
_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)+(0.0506P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                2236
_reflns_number_total             3748
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2054.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Yes' changed to 'yes' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

'_geom_angle_publ_flag' value 'Yes' changed to 'yes' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (8 times).

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 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

'_geom_angle_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (8
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1077.9(8)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               2209310
_cod_database_fobs_code          2209310
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
Ni Ni1 0.0000 0.0000 0.0000 0.0314(3) Uani d S 1
Ni Ni2 0.0000 0.5000 0.0000 0.0330(3) Uani d S 1
N N1 -0.0851(4) -0.0351(4) 0.1114(3) 0.0353(10) Uani d . 1
N N2 0.1562(4) 0.6843(4) 0.0976(3) 0.0335(9) Uani d . 1
O O1 0.1856(3) 0.0917(3) 0.1310(3) 0.0444(9) Uani d . 1
O O2 -0.3824(4) -0.3974(4) -0.0462(4) 0.0641(11) Uani d . 1
H H2 -0.3786 -0.4741 -0.0403 0.096 Uiso calc R 1
O O3 0.0423(3) 0.4496(3) 0.1370(3) 0.0423(9) Uani d . 1
O O4 0.4286(4) 0.6830(4) 0.0602(4) 0.0575(10) Uani d . 1
H H4 0.4010 0.6274 0.0918 0.086 Uiso calc R 1
C C1 -0.0208(5) 0.0252(5) 0.2335(4) 0.0367(12) Uani d . 1
H H1 -0.0769 0.0009 0.2763 0.044 Uiso calc R 1
C C2 0.1265(5) 0.1245(5) 0.3091(4) 0.0336(11) Uani d . 1
C C3 0.2240(5) 0.1502(5) 0.2530(4) 0.0374(12) Uani d . 1
C C4 0.3746(5) 0.2429(5) 0.3299(5) 0.0483(14) Uani d . 1
H H4A 0.4402 0.2578 0.2930 0.058 Uiso calc R 1
C C5 0.4234(5) 0.3104(5) 0.4582(5) 0.0487(14) Uani d . 1
H H5 0.5228 0.3697 0.5072 0.058 Uiso calc R 1
C C6 0.3294(5) 0.2934(5) 0.5177(5) 0.0404(12) Uani d . 1
C C7 0.3816(6) 0.3715(5) 0.6492(5) 0.0515(15) Uani d . 1
H H7 0.4804 0.4331 0.6967 0.062 Uiso calc R 1
C C8 0.2886(6) 0.3573(6) 0.7071(5) 0.0502(14) Uani d . 1
H H8 0.3237 0.4095 0.7937 0.060 Uiso calc R 1
C C9 0.1416(6) 0.2648(6) 0.6366(4) 0.0505(14) Uani d . 1
H H9 0.0790 0.2552 0.6768 0.061 Uiso calc R 1
C C10 0.0866(6) 0.1872(5) 0.5086(4) 0.0425(13) Uani d . 1
H H10 -0.0125 0.1260 0.4636 0.051 Uiso calc R 1
C C11 0.1791(5) 0.1991(5) 0.4441(4) 0.0361(12) Uani d . 1
C C12 -0.2377(5) -0.1449(5) 0.0568(4) 0.0455(13) Uani d . 1
H H12A -0.3039 -0.1275 -0.0118 0.055 Uiso calc R 1
H H12B -0.2744 -0.1351 0.1216 0.055 Uiso calc R 1
C C13 -0.2380(5) -0.2961(5) 0.0072(5) 0.0455(13) Uani d . 1
H H13A -0.1994 -0.3056 -0.0564 0.055 Uiso calc R 1
H H13B -0.1740 -0.3147 0.0761 0.055 Uiso calc R 1
C C14 0.2134(5) 0.7447(5) 0.2200(4) 0.0354(12) Uani d . 1
H H14 0.2815 0.8391 0.2570 0.043 Uiso calc R 1
C C15 0.1833(5) 0.6820(5) 0.3049(4) 0.0336(11) Uani d . 1
C C16 0.1049(5) 0.5329(5) 0.2570(4) 0.0334(11) Uani d . 1
C C17 0.0928(5) 0.4656(5) 0.3429(4) 0.0411(12) Uani d . 1
H H17 0.0428 0.3662 0.3119 0.049 Uiso calc R 1
C C18 0.1525(5) 0.5435(5) 0.4680(5) 0.0438(13) Uani d . 1
H H18 0.1459 0.4959 0.5222 0.053 Uiso calc R 1
C C19 0.2254(5) 0.6960(5) 0.5206(4) 0.0374(12) Uani d . 1
C C20 0.2812(5) 0.7759(6) 0.6517(5) 0.0492(14) Uani d . 1
H H20 0.2696 0.7282 0.7047 0.059 Uiso calc R 1
C C21 0.3517(6) 0.9220(7) 0.7019(5) 0.0583(16) Uani d . 1
H H21 0.3894 0.9736 0.7888 0.070 Uiso calc R 1
C C22 0.3670(5) 0.9934(6) 0.6227(5) 0.0532(15) Uani d . 1
H H22 0.4136 1.0936 0.6569 0.064 Uiso calc R 1
C C23 0.3143(5) 0.9184(5) 0.4946(4) 0.0434(13) Uani d . 1
H H23 0.3264 0.9686 0.4434 0.052 Uiso calc R 1
C C24 0.2427(5) 0.7673(5) 0.4394(4) 0.0350(11) Uani d . 1
C C25 0.2215(5) 0.7673(5) 0.0351(4) 0.0407(12) Uani d . 1
H H25A 0.2897 0.8626 0.0977 0.049 Uiso calc R 1
H H25B 0.1429 0.7801 -0.0282 0.049 Uiso calc R 1
C C26 0.3029(6) 0.6942(6) -0.0275(5) 0.0489(14) Uani d . 1
H H26A 0.2354 0.5979 -0.0883 0.059 Uiso calc R 1
H H26B 0.3351 0.7481 -0.0738 0.059 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'
Ni Ni 0.3393 1.1124 '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'
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 . 180.0(3) yes
O1 Ni1 N1 2 2 91.48(15) yes
O1 Ni1 N1 . 2 88.53(15) ?
O1 Ni1 N1 2 . 88.52(15) ?
O1 Ni1 N1 . . 91.47(15) yes
N1 Ni1 N1 2 . 180.0(3) yes
O3 Ni2 O3 2_565 . 180.00(17) yes
O3 Ni2 N2 2_565 . 88.60(15) ?
O3 Ni2 N2 . . 91.40(15) yes
O3 Ni2 N2 2_565 2_565 91.40(15) yes
O3 Ni2 N2 . 2_565 88.60(15) ?
N2 Ni2 N2 . 2_565 180.0 yes
C1 N1 C12 . . 115.1(4) ?
C1 N1 Ni1 . . 125.7(3) ?
C12 N1 Ni1 . . 119.1(3) ?
C14 N2 C25 . . 115.4(4) ?
C14 N2 Ni2 . . 124.0(3) ?
C25 N2 Ni2 . . 120.7(3) ?
C3 O1 Ni1 . . 129.2(3) ?
C13 O2 H2 . . 109.5 ?
C16 O3 Ni2 . . 128.9(3) ?
C26 O4 H4 . . 109.5 ?
N1 C1 C2 . . 126.6(4) ?
N1 C1 H1 . . 116.7 ?
C2 C1 H1 . . 116.7 ?
C3 C2 C1 . . 119.7(4) ?
C3 C2 C11 . . 119.2(4) ?
C1 C2 C11 . . 121.0(4) ?
O1 C3 C2 . . 123.8(4) ?
O1 C3 C4 . . 116.4(5) ?
C2 C3 C4 . . 119.8(4) ?
C5 C4 C3 . . 120.1(5) ?
C5 C4 H4A . . 119.9 ?
C3 C4 H4A . . 119.9 ?
C4 C5 C6 . . 122.2(5) ?
C4 C5 H5 . . 118.9 ?
C6 C5 H5 . . 118.9 ?
C5 C6 C7 . . 120.6(5) ?
C5 C6 C11 . . 119.1(5) ?
C7 C6 C11 . . 120.3(5) ?
C8 C7 C6 . . 120.6(5) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C7 C8 C9 . . 119.7(5) ?
C7 C8 H8 . . 120.1 ?
C9 C8 H8 . . 120.1 ?
C10 C9 C8 . . 121.4(5) ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
C9 C10 C11 . . 120.9(5) ?
C9 C10 H10 . . 119.6 ?
C11 C10 H10 . . 119.6 ?
C6 C11 C10 . . 117.1(4) ?
C6 C11 C2 . . 119.4(5) ?
C10 C11 C2 . . 123.5(4) ?
N1 C12 C13 . . 111.2(4) ?
N1 C12 H12A . . 109.4 ?
C13 C12 H12A . . 109.4 ?
N1 C12 H12B . . 109.4 ?
C13 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
O2 C13 C12 . . 110.4(4) ?
O2 C13 H13A . . 109.6 ?
C12 C13 H13A . . 109.6 ?
O2 C13 H13B . . 109.6 ?
C12 C13 H13B . . 109.6 ?
H13A C13 H13B . . 108.1 ?
N2 C14 C15 . . 127.0(4) ?
N2 C14 H14 . . 116.5 ?
C15 C14 H14 . . 116.5 ?
C16 C15 C14 . . 118.5(4) ?
C16 C15 C24 . . 120.0(4) ?
C14 C15 C24 . . 121.3(4) ?
O3 C16 C15 . . 124.0(4) ?
O3 C16 C17 . . 116.9(4) ?
C15 C16 C17 . . 119.1(4) ?
C18 C17 C16 . . 120.9(5) ?
C18 C17 H17 . . 119.6 ?
C16 C17 H17 . . 119.6 ?
C17 C18 C19 . . 122.2(5) ?
C17 C18 H18 . . 118.9 ?
C19 C18 H18 . . 118.9 ?
C20 C19 C24 . . 120.1(5) ?
C20 C19 C18 . . 121.0(5) ?
C24 C19 C18 . . 118.9(4) ?
C21 C20 C19 . . 120.9(5) ?
C21 C20 H20 . . 119.6 ?
C19 C20 H20 . . 119.6 ?
C20 C21 C22 . . 119.6(5) ?
C20 C21 H21 . . 120.2 ?
C22 C21 H21 . . 120.2 ?
C23 C22 C21 . . 120.9(5) ?
C23 C22 H22 . . 119.6 ?
C21 C22 H22 . . 119.6 ?
C22 C23 C24 . . 121.3(5) ?
C22 C23 H23 . . 119.4 ?
C24 C23 H23 . . 119.4 ?
C23 C24 C19 . . 117.3(4) ?
C23 C24 C15 . . 123.9(4) ?
C19 C24 C15 . . 118.7(4) ?
N2 C25 C26 . . 112.5(4) ?
N2 C25 H25A . . 109.1 ?
C26 C25 H25A . . 109.1 ?
N2 C25 H25B . . 109.1 ?
C26 C25 H25B . . 109.1 ?
H25A C25 H25B . . 107.8 ?
O4 C26 C25 . . 112.9(4) ?
O4 C26 H26A . . 109.0 ?
C25 C26 H26A . . 109.0 ?
O4 C26 H26B . . 109.0 ?
C25 C26 H26B . . 109.0 ?
H26A C26 H26B . . 107.8 ?
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 1.826(3) yes
Ni1 O1 . 1.826(3) ?
Ni1 N1 2 1.904(4) yes
Ni1 N1 . 1.904(4) ?
Ni2 O3 2_565 1.818(3) yes
Ni2 O3 . 1.818(3) ?
Ni2 N2 . 1.907(4) ?
Ni2 N2 2_565 1.907(4) yes
N1 C1 . 1.288(5) ?
N1 C12 . 1.491(5) ?
N2 C14 . 1.292(5) ?
N2 C25 . 1.477(6) ?
O1 C3 . 1.309(5) ?
O2 C13 . 1.398(5) ?
O2 H2 . 0.8200 ?
O3 C16 . 1.301(5) ?
O4 C26 . 1.419(5) ?
O4 H4 . 0.8200 ?
C1 C2 . 1.413(6) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.399(6) ?
C2 C11 . 1.442(6) ?
C3 C4 . 1.419(6) ?
C4 C5 . 1.368(6) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.390(7) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.413(6) ?
C6 C11 . 1.417(6) ?
C7 C8 . 1.364(7) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.386(7) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.372(6) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.420(6) ?
C10 H10 . 0.9300 ?
C12 C13 . 1.505(6) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.432(6) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.400(6) ?
C15 C24 . 1.448(6) ?
C16 C17 . 1.422(6) ?
C17 C18 . 1.341(6) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.419(6) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.407(6) ?
C19 C24 . 1.411(6) ?
C20 C21 . 1.359(7) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.386(7) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.372(6) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.404(6) ?
C23 H23 . 0.9300 ?
C25 C26 . 1.495(6) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 H26A . 0.9700 ?
C26 H26B . 0.9700 ?
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
O2 H2 O4 2_555 0.82 2.01 2.813(5) 164.2
O4 H4 O2 2_555 0.82 2.22 2.813(5) 129.1
C18 H18 Cg 1_555 0.93 2.7582(9) 3.4914(11) 136.4
C22 H22 Cg 1_565 0.93 3.0610(8) 3.6071(12) 119.2
