#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/61/2206146.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_2206146
loop_
_publ_author_name
'Ming-Li Liu'
'Jian-Min Dou'
'Da-Qi Wang'
'Da-Cheng Li'
_publ_section_title
;
 [2-Oxido-1-naphthaldehyde
 (2-hydroxybenzoyl)hydrazonato]pyridinenickel(II)
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1366
_journal_page_last               m1367
_journal_paper_doi               10.1107/S1600536805018672
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Ni (C18 H12 N2 O3) (C5 H5 N)]'
_chemical_formula_moiety         'C23 H17 N3 Ni O3'
_chemical_formula_sum            'C23 H17 N3 Ni O3'
_chemical_formula_weight         442.11
_chemical_name_systematic
;
[2-Oxido-1-naphthaldehyde (2-hydroxybenzoyl)hydrazonato]pyridinenickel(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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.474(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.768(4)
_cell_length_b                   8.164(3)
_cell_length_c                   20.428(7)
_cell_measurement_reflns_used    3286
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.527
_cell_measurement_theta_min      2.35
_cell_volume                     1891.5(11)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens SMART 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  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0603
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9346
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.058
_exptl_absorpt_correction_T_max  0.8747
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange--red
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.245
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0377
_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)+(0.0172P)²+0.829P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                2558
_reflns_number_total             3321
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6433.cif
_cod_data_source_block           I
_cod_original_cell_volume        1891.5(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206146
_cod_database_fobs_code          2206146
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_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_type_symbol
Ni1 0.37075(3) 0.85611(5) 0.538911(16) 0.04388(14) Uani d . 1 Ni
N1 0.40049(19) 0.8656(3) 0.45194(11) 0.0424(5) Uani d . 1 N
N2 0.50205(19) 0.7842(3) 0.44732(11) 0.0476(6) Uani d . 1 N
N3 0.3658(2) 0.8511(3) 0.63608(11) 0.0506(6) Uani d . 1 N
O1 0.51244(16) 0.7260(3) 0.55872(9) 0.0519(5) Uani d . 1 O
O2 0.6524(2) 0.6433(3) 0.39330(11) 0.0838(8) Uani d . 1 O
H2 0.5953 0.6994 0.3946 0.126 Uiso calc R 1 H
O3 0.23011(16) 0.9765(3) 0.50982(9) 0.0532(5) Uani d . 1 O
C1 0.5521(2) 0.7129(4) 0.50576(14) 0.0442(7) Uani d . 1 C
C2 0.6581(2) 0.6122(3) 0.51104(14) 0.0449(7) Uani d . 1 C
C3 0.7022(3) 0.5805(4) 0.45565(15) 0.0583(8) Uani d . 1 C
C4 0.8004(3) 0.4808(5) 0.46312(18) 0.0728(10) Uani d . 1 C
H4 0.8290 0.4580 0.4258 0.087 Uiso calc R 1 H
C5 0.8551(3) 0.4161(4) 0.5253(2) 0.0708(10) Uani d . 1 C
H5 0.9215 0.3506 0.5301 0.085 Uiso calc R 1 H
C6 0.8133(3) 0.4465(4) 0.58075(18) 0.0655(9) Uani d . 1 C
H6 0.8508 0.4019 0.6229 0.079 Uiso calc R 1 H
C7 0.7155(2) 0.5437(4) 0.57309(15) 0.0530(7) Uani d . 1 C
H7 0.6870 0.5642 0.6106 0.064 Uiso calc R 1 H
C8 0.3402(2) 0.9424(4) 0.39846(13) 0.0465(7) Uani d . 1 C
H8 0.3695 0.9428 0.3605 0.056 Uiso calc R 1 H
C9 0.2322(2) 1.0262(3) 0.39368(13) 0.0431(6) Uani d . 1 C
C10 0.1841(2) 1.0377(3) 0.44943(14) 0.0466(7) Uani d . 1 C
C11 0.0754(3) 1.1242(4) 0.44075(16) 0.0574(8) Uani d . 1 C
H11 0.0417 1.1308 0.4770 0.069 Uiso calc R 1 H
C12 0.0205(3) 1.1963(4) 0.38136(17) 0.0606(8) Uani d . 1 C
H12 -0.0498 1.2518 0.3778 0.073 Uiso calc R 1 H
C13 0.0670(3) 1.1898(4) 0.32449(15) 0.0529(7) Uani d . 1 C
C14 0.1734(2) 1.1041(3) 0.32979(14) 0.0466(7) Uani d . 1 C
C15 0.2153(3) 1.1018(4) 0.27164(14) 0.0550(8) Uani d . 1 C
H15 0.2854 1.0472 0.2735 0.066 Uiso calc R 1 H
C16 0.1569(3) 1.1770(4) 0.21231(16) 0.0628(9) Uani d . 1 C
H16 0.1871 1.1716 0.1747 0.075 Uiso calc R 1 H
C17 0.0524(3) 1.2613(4) 0.20799(17) 0.0664(9) Uani d . 1 C
H17 0.0126 1.3127 0.1678 0.080 Uiso calc R 1 H
C18 0.0097(3) 1.2673(4) 0.26308(17) 0.0649(9) Uani d . 1 C
H18 -0.0598 1.3245 0.2603 0.078 Uiso calc R 1 H
C19 0.2891(3) 0.9364(5) 0.65907(15) 0.0632(9) Uani d . 1 C
H19 0.2329 0.9984 0.6284 0.076 Uiso calc R 1 H
C20 0.2888(3) 0.9375(5) 0.72623(16) 0.0718(10) Uani d . 1 C
H20 0.2324 0.9979 0.7401 0.086 Uiso calc R 1 H
C21 0.3704(3) 0.8509(4) 0.77188(16) 0.0710(10) Uani d . 1 C
H21 0.3724 0.8519 0.8177 0.085 Uiso calc R 1 H
C22 0.4495(3) 0.7623(5) 0.74923(17) 0.0852(12) Uani d . 1 C
H22 0.5066 0.7007 0.7795 0.102 Uiso calc R 1 H
C23 0.4450(3) 0.7639(5) 0.68185(17) 0.0805(12) Uani d . 1 C
H23 0.4995 0.7014 0.6671 0.097 Uiso calc R 1 H
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
O3 Ni1 N1 92.82(9)
O3 Ni1 O1 173.87(8)
N1 Ni1 O1 81.61(8)
O3 Ni1 N3 93.91(9)
N1 Ni1 N3 171.30(9)
O1 Ni1 N3 91.89(9)
C8 N1 N2 117.5(2)
C8 N1 Ni1 127.73(19)
N2 N1 Ni1 114.76(16)
C1 N2 N1 109.5(2)
C19 N3 C23 116.6(3)
C19 N3 Ni1 123.0(2)
C23 N3 Ni1 120.4(2)
C1 O1 Ni1 110.83(17)
C3 O2 H2 109.5
C10 O3 Ni1 127.33(18)
O1 C1 N2 123.3(3)
O1 C1 C2 118.2(2)
N2 C1 C2 118.5(2)
C7 C2 C3 118.3(3)
C7 C2 C1 119.2(3)
C3 C2 C1 122.5(3)
O2 C3 C4 117.6(3)
O2 C3 C2 122.3(3)
C4 C3 C2 120.0(3)
C5 C4 C3 120.0(3)
C5 C4 H4 120.0
C3 C4 H4 120.0
C4 C5 C6 120.8(3)
C4 C5 H5 119.6
C6 C5 H5 119.6
C5 C6 C7 119.0(3)
C5 C6 H6 120.5
C7 C6 H6 120.5
C6 C7 C2 121.8(3)
C6 C7 H7 119.1
C2 C7 H7 119.1
N1 C8 C9 124.7(3)
N1 C8 H8 117.7
C9 C8 H8 117.7
C10 C9 C8 121.5(2)
C10 C9 C14 120.1(3)
C8 C9 C14 118.4(2)
O3 C10 C9 125.8(3)
O3 C10 C11 115.9(2)
C9 C10 C11 118.2(3)
C12 C11 C10 121.6(3)
C12 C11 H11 119.2
C10 C11 H11 119.2
C11 C12 C13 121.8(3)
C11 C12 H12 119.1
C13 C12 H12 119.1
C18 C13 C12 121.3(3)
C18 C13 C14 119.7(3)
C12 C13 C14 119.1(3)
C15 C14 C13 116.5(3)
C15 C14 C9 124.4(3)
C13 C14 C9 119.1(3)
C16 C15 C14 122.5(3)
C16 C15 H15 118.8
C14 C15 H15 118.8
C15 C16 C17 120.3(3)
C15 C16 H16 119.8
C17 C16 H16 119.8
C18 C17 C16 119.0(3)
C18 C17 H17 120.5
C16 C17 H17 120.5
C17 C18 C13 122.0(3)
C17 C18 H18 119.0
C13 C18 H18 119.0
N3 C19 C20 122.9(3)
N3 C19 H19 118.6
C20 C19 H19 118.6
C21 C20 C19 119.8(3)
C21 C20 H20 120.1
C19 C20 H20 120.1
C20 C21 C22 118.2(3)
C20 C21 H21 120.9
C22 C21 H21 120.9
C21 C22 C23 119.7(3)
C21 C22 H22 120.2
C23 C22 H22 120.2
N3 C23 C22 122.9(3)
N3 C23 H23 118.5
C22 C23 H23 118.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni1 O3 1.880(2)
Ni1 N1 1.902(2)
Ni1 O1 1.927(2)
Ni1 N3 2.002(2)
N1 C8 1.295(3)
N1 N2 1.393(3)
N2 C1 1.317(3)
N3 C19 1.321(4)
N3 C23 1.336(4)
O1 C1 1.292(3)
O2 C3 1.353(4)
O2 H2 0.82
O3 C10 1.307(3)
C1 C2 1.474(4)
C2 C7 1.385(4)
C2 C3 1.389(4)
C3 C4 1.388(4)
C4 C5 1.368(5)
C4 H4 0.93
C5 C6 1.372(4)
C5 H5 0.93
C6 C7 1.372(4)
C6 H6 0.93
C7 H7 0.93
C8 C9 1.424(4)
C8 H8 0.93
C9 C10 1.403(4)
C9 C14 1.451(4)
C10 C11 1.430(4)
C11 C12 1.348(4)
C11 H11 0.93
C12 C13 1.410(4)
C12 H12 0.93
C13 C18 1.406(4)
C13 C14 1.413(4)
C14 C15 1.403(4)
C15 C16 1.369(4)
C15 H15 0.93
C16 C17 1.391(5)
C16 H16 0.93
C17 C18 1.351(5)
C17 H17 0.93
C18 H18 0.93
C19 C20 1.373(4)
C19 H19 0.93
C20 C21 1.347(5)
C20 H20 0.93
C21 C22 1.354(5)
C21 H21 0.93
C22 C23 1.363(4)
C22 H22 0.93
C23 H23 0.93
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2 N2 0.82 1.86 2.591(3) 147
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
O3 Ni1 N1 C8 3.8(2)
O1 Ni1 N1 C8 -178.8(3)
O3 Ni1 N1 N2 -178.69(18)
O1 Ni1 N1 N2 -1.26(17)
C8 N1 N2 C1 -179.8(2)
Ni1 N1 N2 C1 2.4(3)
O3 Ni1 N3 C19 -8.4(3)
O1 Ni1 N3 C19 173.6(3)
O3 Ni1 N3 C23 174.2(3)
O1 Ni1 N3 C23 -3.8(3)
N1 Ni1 O1 C1 -0.14(18)
N3 Ni1 O1 C1 -174.34(19)
N1 Ni1 O3 C10 -1.0(2)
N3 Ni1 O3 C10 173.5(2)
Ni1 O1 C1 N2 1.7(3)
Ni1 O1 C1 C2 -177.91(19)
N1 N2 C1 O1 -2.7(4)
N1 N2 C1 C2 176.9(2)
O1 C1 C2 C7 -3.8(4)
N2 C1 C2 C7 176.5(3)
O1 C1 C2 C3 175.0(3)
N2 C1 C2 C3 -4.7(4)
C7 C2 C3 O2 -179.4(3)
C1 C2 C3 O2 1.8(5)
C7 C2 C3 C4 0.7(5)
C1 C2 C3 C4 -178.1(3)
O2 C3 C4 C5 179.0(3)
C2 C3 C4 C5 -1.1(5)
C3 C4 C5 C6 0.8(6)
C4 C5 C6 C7 -0.2(5)
C5 C6 C7 C2 -0.2(5)
C3 C2 C7 C6 -0.1(5)
C1 C2 C7 C6 178.8(3)
N2 N1 C8 C9 177.4(2)
Ni1 N1 C8 C9 -5.1(4)
N1 C8 C9 C10 2.7(4)
N1 C8 C9 C14 -178.8(3)
Ni1 O3 C10 C9 -0.6(4)
Ni1 O3 C10 C11 179.8(2)
C8 C9 C10 O3 0.2(4)
C14 C9 C10 O3 -178.2(3)
C8 C9 C10 C11 179.9(3)
C14 C9 C10 C11 1.4(4)
O3 C10 C11 C12 178.4(3)
C9 C10 C11 C12 -1.3(4)
C10 C11 C12 C13 0.3(5)
C11 C12 C13 C18 -179.2(3)
C11 C12 C13 C14 0.6(5)
C18 C13 C14 C15 -0.3(4)
C12 C13 C14 C15 180.0(3)
C18 C13 C14 C9 179.3(3)
C12 C13 C14 C9 -0.4(4)
C10 C9 C14 C15 179.0(3)
C8 C9 C14 C15 0.5(4)
C10 C9 C14 C13 -0.6(4)
C8 C9 C14 C13 -179.1(3)
C13 C14 C15 C16 -0.5(4)
C9 C14 C15 C16 180.0(3)
C14 C15 C16 C17 0.7(5)
C15 C16 C17 C18 -0.2(5)
C16 C17 C18 C13 -0.6(5)
C12 C13 C18 C17 -179.5(3)
C14 C13 C18 C17 0.8(5)
C23 N3 C19 C20 0.0(5)
Ni1 N3 C19 C20 -177.5(3)
N3 C19 C20 C21 1.0(6)
C19 C20 C21 C22 -1.2(6)
C20 C21 C22 C23 0.4(6)
C19 N3 C23 C22 -0.8(6)
Ni1 N3 C23 C22 176.7(3)
C21 C22 C23 N3 0.7(7)
