#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229900.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_2229900
loop_
_publ_author_name
'Zou, Li-Fei'
'Yang, Xiu-Yun'
'Gao, Ying'
'Yao, Hai-Bo'
'Li, Yun-Hui'
_publ_section_title
;
 (2-Oxido-1-naphthaldehyde
 benzoylhydrazonato-κ³N,N',O)pyridinecopper(II)
;
_journal_coeditor_code           ZQ2095
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m511
_journal_paper_doi               10.1107/S1600536811011081
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu (C18 H12 N2 O2) (C5 H5 N)]'
_chemical_formula_moiety         'C23 H17 Cu N3 O2'
_chemical_formula_sum            'C23 H17 Cu N3 O2'
_chemical_formula_weight         430.94
_chemical_name_common
;
N-[(2-oxido-1-naphthyl-κO)methylidene]benzohydrazidato-\
κ²N,O](pyridine)copper(II)
;
_chemical_name_systematic
;(2-Oxido-1-naphthaldehyde benzoylhydrazonato-κ³N,N',
O)pyridinecopper(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                 106.2470(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6196(6)
_cell_length_b                   8.4254(4)
_cell_length_c                   19.6194(10)
_cell_measurement_reflns_used    9033
_cell_measurement_temperature    185(2)
_cell_measurement_theta_max      51.94
_cell_measurement_theta_min      4.80
_cell_volume                     1844.03(16)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'DIAMOND  (Brandenburg, 1999)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      185(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8559
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    1.210
_exptl_absorpt_correction_T_max  0.8886
_exptl_absorpt_correction_T_min  0.8489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0353P)²+1.0945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0856
_reflns_number_gt                2860
_reflns_number_total             3619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            zq2095.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229900
_cod_database_fobs_code          2229900
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.86976(3) 0.13588(4) 0.539632(16) 0.02191(11) Uani d . 1 . .
N N1 0.89789(18) 0.1188(2) 0.44895(11) 0.0200(5) Uani d . 1 . .
N N2 0.99966(18) 0.1976(3) 0.44156(11) 0.0216(5) Uani d . 1 . .
N N3 0.86766(19) 0.1483(2) 0.64115(11) 0.0226(5) Uani d . 1 . .
O O1 0.72604(15) 0.0186(2) 0.51138(9) 0.0247(4) Uani d . 1 . .
O O2 1.00963(15) 0.2688(2) 0.55668(9) 0.0238(4) Uani d . 1 . .
C C1 0.7084(2) -0.1291(3) 0.26471(14) 0.0265(6) Uani d . 1 . .
H H1 0.7807 -0.0755 0.2655 0.032 Uiso calc R 1 . .
C C2 0.6465(3) -0.2069(3) 0.20399(14) 0.0300(6) Uani d . 1 . .
H H2 0.6762 -0.2046 0.1635 0.036 Uiso calc R 1 . .
C C3 0.5411(3) -0.2891(3) 0.20059(15) 0.0306(6) Uani d . 1 . .
H H3 0.4997 -0.3440 0.1586 0.037 Uiso calc R 1 . .
C C4 0.4982(3) -0.2894(3) 0.25876(15) 0.0313(7) Uani d . 1 . .
H H4 0.4259 -0.3444 0.2567 0.038 Uiso calc R 1 . .
C C5 0.5588(2) -0.2100(3) 0.32154(14) 0.0261(6) Uani d . 1 . .
C C6 0.5135(2) -0.2110(3) 0.38178(15) 0.0295(6) Uani d . 1 . .
H H6 0.4416 -0.2672 0.3794 0.035 Uiso calc R 1 . .
C C7 0.5702(2) -0.1339(3) 0.44258(14) 0.0267(6) Uani d . 1 . .
H H7 0.5366 -0.1366 0.4815 0.032 Uiso calc R 1 . .
C C8 0.6791(2) -0.0489(3) 0.44957(13) 0.0221(6) Uani d . 1 . .
C C9 0.7276(2) -0.0447(3) 0.39116(13) 0.0205(5) Uani d . 1 . .
C C10 0.6671(2) -0.1266(3) 0.32608(13) 0.0225(6) Uani d . 1 . .
C C11 0.8363(2) 0.0379(3) 0.39455(13) 0.0216(6) Uani d . 1 . .
H H11 0.8658 0.0333 0.3541 0.026 Uiso calc R 1 . .
C C12 1.0481(2) 0.2750(3) 0.50057(13) 0.0213(6) Uani d . 1 . .
C C13 1.1522(2) 0.3790(3) 0.50397(14) 0.0219(6) Uani d . 1 . .
C C14 1.1922(3) 0.4090(3) 0.44463(15) 0.0329(7) Uani d . 1 . .
H H14 1.1537 0.3597 0.4006 0.039 Uiso calc R 1 . .
C C15 1.2877(3) 0.5103(4) 0.44947(16) 0.0385(7) Uani d . 1 . .
H H15 1.3142 0.5301 0.4086 0.046 Uiso calc R 1 . .
C C16 1.3449(3) 0.5828(3) 0.51292(17) 0.0361(7) Uani d . 1 . .
H H16 1.4105 0.6522 0.5158 0.043 Uiso calc R 1 . .
C C17 1.3063(2) 0.5537(3) 0.57197(16) 0.0328(7) Uani d . 1 . .
H H17 1.3455 0.6032 0.6158 0.039 Uiso calc R 1 . .
C C18 1.2107(2) 0.4527(3) 0.56769(14) 0.0262(6) Uani d . 1 . .
H H18 1.1847 0.4334 0.6087 0.031 Uiso calc R 1 . .
C C19 0.9510(2) 0.2352(3) 0.68806(15) 0.0323(7) Uani d . 1 . .
H H19 1.0071 0.2946 0.6714 0.039 Uiso calc R 1 . .
C C20 0.9577(3) 0.2408(4) 0.75936(15) 0.0350(7) Uani d . 1 . .
H H20 1.0176 0.3027 0.7911 0.042 Uiso calc R 1 . .
C C21 0.8762(3) 0.1554(3) 0.78380(14) 0.0313(7) Uani d . 1 . .
H H21 0.8795 0.1564 0.8327 0.038 Uiso calc R 1 . .
C C22 0.7900(3) 0.0686(4) 0.73614(15) 0.0332(7) Uani d . 1 . .
H H22 0.7319 0.0101 0.7515 0.040 Uiso calc R 1 . .
C C23 0.7889(2) 0.0676(3) 0.66537(14) 0.0275(6) Uani d . 1 . .
H H23 0.7294 0.0067 0.6328 0.033 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'
Cu Cu 0.3201 1.2651 '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 Cu1 N1 . . 93.17(8) y
O1 Cu1 O2 . . 172.59(7) y
N1 Cu1 O2 . . 81.30(8) y
O1 Cu1 N3 . . 93.65(8) y
N1 Cu1 N3 . . 171.07(8) y
O2 Cu1 N3 . . 92.37(8) y
C11 N1 N2 . . 116.8(2) ?
C11 N1 Cu1 . . 127.48(17) ?
N2 N1 Cu1 . . 115.64(15) ?
C12 N2 N1 . . 108.15(19) ?
C23 N3 C19 . . 117.9(2) ?
C23 N3 Cu1 . . 121.99(18) ?
C19 N3 Cu1 . . 120.08(17) ?
C8 O1 Cu1 . . 127.16(16) ?
C12 O2 Cu1 . . 110.51(16) ?
C2 C1 C10 . . 121.7(3) ?
C2 C1 H1 . . 119.2 ?
C10 C1 H1 . . 119.2 ?
C1 C2 C3 . . 121.3(3) ?
C1 C2 H2 . . 119.4 ?
C3 C2 H2 . . 119.4 ?
C4 C3 C2 . . 118.8(3) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?
C3 C4 C5 . . 121.4(3) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C4 C5 C6 . . 121.0(3) ?
C4 C5 C10 . . 120.5(3) ?
C6 C5 C10 . . 118.5(2) ?
C7 C6 C5 . . 121.8(2) ?
C7 C6 H6 . . 119.1 ?
C5 C6 H6 . . 119.1 ?
C6 C7 C8 . . 121.7(2) ?
C6 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
O1 C8 C9 . . 125.6(2) ?
O1 C8 C7 . . 115.8(2) ?
C9 C8 C7 . . 118.6(2) ?
C8 C9 C11 . . 121.6(2) ?
C8 C9 C10 . . 119.9(2) ?
C11 C9 C10 . . 118.6(2) ?
C1 C10 C5 . . 116.4(2) ?
C1 C10 C9 . . 124.1(2) ?
C5 C10 C9 . . 119.6(2) ?
N1 C11 C9 . . 124.8(2) ?
N1 C11 H11 . . 117.6 ?
C9 C11 H11 . . 117.6 ?
O2 C12 N2 . . 124.3(2) ?
O2 C12 C13 . . 117.2(2) ?
N2 C12 C13 . . 118.6(2) ?
C18 C13 C14 . . 118.5(2) ?
C18 C13 C12 . . 119.5(2) ?
C14 C13 C12 . . 122.0(2) ?
C15 C14 C13 . . 120.3(3) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C16 C15 C14 . . 120.7(3) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C17 C16 C15 . . 119.5(3) ?
C17 C16 H16 . . 120.2 ?
C15 C16 H16 . . 120.2 ?
C16 C17 C18 . . 120.2(3) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C17 C18 C13 . . 120.7(3) ?
C17 C18 H18 . . 119.6 ?
C13 C18 H18 . . 119.6 ?
N3 C19 C20 . . 122.5(3) ?
N3 C19 H19 . . 118.8 ?
C20 C19 H19 . . 118.8 ?
C21 C20 C19 . . 119.0(3) ?
C21 C20 H20 . . 120.5 ?
C19 C20 H20 . . 120.5 ?
C22 C21 C20 . . 118.8(3) ?
C22 C21 H21 . . 120.6 ?
C20 C21 H21 . . 120.6 ?
C21 C22 C23 . . 119.1(3) ?
C21 C22 H22 . . 120.4 ?
C23 C22 H22 . . 120.4 ?
N3 C23 C22 . . 122.7(3) ?
N3 C23 H23 . . 118.6 ?
C22 C23 H23 . . 118.6 ?
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
Cu1 O1 . 1.8853(17) y
Cu1 N1 . 1.902(2) y
Cu1 O2 . 1.9243(17) y
Cu1 N3 . 2.001(2) y
N1 C11 . 1.300(3) ?
N1 N2 . 1.398(3) ?
N2 C12 . 1.311(3) ?
N3 C23 . 1.331(3) ?
N3 C19 . 1.349(3) ?
O1 C8 . 1.312(3) ?
O2 C12 . 1.300(3) ?
C1 C2 . 1.374(4) ?
C1 C10 . 1.415(4) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.392(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.367(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.405(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.422(4) ?
C5 C10 . 1.423(4) ?
C6 C7 . 1.356(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.427(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.412(3) ?
C9 C11 . 1.428(3) ?
C9 C10 . 1.449(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.480(3) ?
C13 C18 . 1.391(4) ?
C13 C14 . 1.392(4) ?
C14 C15 . 1.381(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.379(4) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.376(4) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.384(4) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 C20 . 1.380(4) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.378(4) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.374(4) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.385(4) ?
C22 H22 . 0.9500 ?
C23 H23 . 0.9500 ?
