#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/04/2220436.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_2220436
loop_
_publ_author_name
'Mohd Lair, Nooraziah'
'Mohd Ali, Hapipah'
'Ng, Seik Weng'
_publ_section_title
'[N'-(4-Methoxy-2-oxidobenzylidene)4-nitrobenzohydrazidato-κ³O,N,O'](pyridine-κN)copper(II)'
_journal_coeditor_code           BT2838
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m121
_journal_paper_doi               10.1107/S1600536808042803
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C15 H11 N3 O5) (C5 H5 N)]'
_chemical_formula_moiety         'C20 H16 Cu N4 O5'
_chemical_formula_sum            'C20 H16 Cu N4 O5'
_chemical_formula_weight         455.91
_chemical_name_systematic
;
[N'-(4-Methoxy-2-oxidobenzylidene)-4-nitrobenzohydrazidato-
κ³O,N,O'](pyridine-κN)copper(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                98.0630(10)
_cell_angle_beta                 92.0110(10)
_cell_angle_gamma                107.0880(10)
_cell_formula_units_Z            2
_cell_length_a                   6.35290(10)
_cell_length_b                   9.8409(2)
_cell_length_c                   15.1303(3)
_cell_measurement_reflns_used    3716
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.2
_cell_measurement_theta_min      2.4
_cell_volume                     892.31(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'pubCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       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  0.0130
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6268
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.269
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0494P)²+0.535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                3605
_reflns_number_total             3942
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2838.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.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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 '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.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_database_code               2220436
_cod_database_fobs_code          2220436
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_disorder_assembly
_atom_site_disorder_group
Cu Cu1 1.14506(4) 0.70062(2) 0.728016(14) 0.01312(9) Uani d . 1 . .
N N1 0.9381(3) 0.64556(17) 0.62386(11) 0.0150(3) Uani d . 1 . .
N N2 1.0273(3) 0.68298(18) 0.54424(10) 0.0159(3) Uani d . 1 . .
N N3 1.7555(3) 0.93172(18) 0.27544(11) 0.0189(4) Uani d . 1 . .
N N4 1.3792(3) 0.78081(17) 0.82931(11) 0.0145(3) Uani d . 1 . .
O O1 0.9305(2) 0.61658(15) 0.80405(9) 0.0163(3) Uani d . 1 . .
O O2 0.2533(2) 0.39329(16) 0.90700(9) 0.0199(3) Uani d . 1 . .
O O3 1.3444(2) 0.77637(15) 0.64095(9) 0.0159(3) Uani d . 1 . .
O O4 1.6632(3) 0.91481(17) 0.20033(9) 0.0247(3) Uani d . 1 . .
O O5 1.9560(3) 0.9856(2) 0.29243(11) 0.0311(4) Uani d . 1 . .
C C1 0.7183(3) 0.5521(2) 0.78294(13) 0.0139(4) Uani d . 1 . .
C C2 0.5869(3) 0.5009(2) 0.85092(13) 0.0152(4) Uani d . 1 . .
H H2 0.6540 0.5120 0.9097 0.018 Uiso calc R 1 . .
C C3 0.3615(3) 0.4346(2) 0.83442(13) 0.0149(4) Uani d . 1 . .
C C4 0.2562(3) 0.4147(2) 0.74829(13) 0.0151(4) Uani d . 1 . .
H H4 0.1016 0.3693 0.7371 0.018 Uiso calc R 1 . .
C C5 0.3837(3) 0.4630(2) 0.68048(13) 0.0146(4) Uani d . 1 . .
H H5 0.3142 0.4495 0.6219 0.018 Uiso calc R 1 . .
C C6 0.6124(3) 0.5313(2) 0.69468(12) 0.0140(4) Uani d . 1 . .
C C7 0.7290(3) 0.5785(2) 0.61964(12) 0.0149(4) Uani d . 1 . .
H H7 0.6471 0.5592 0.5631 0.018 Uiso calc R 1 . .
C C8 0.0219(3) 0.3204(3) 0.89270(15) 0.0247(5) Uani d . 1 . .
H H8A -0.0352 0.2939 0.9492 0.037 Uiso calc R 1 . .
H H8B -0.0038 0.2333 0.8484 0.037 Uiso calc R 1 . .
H H8C -0.0540 0.3840 0.8707 0.037 Uiso calc R 1 . .
C C9 1.2393(3) 0.7493(2) 0.56222(12) 0.0140(4) Uani d . 1 . .
C C10 1.3714(3) 0.79538(19) 0.48671(12) 0.0142(4) Uani d . 1 . .
C C11 1.2684(3) 0.7902(2) 0.40223(13) 0.0162(4) Uani d . 1 . .
H H11 1.1119 0.7555 0.3927 0.019 Uiso calc R 1 . .
C C12 1.3932(3) 0.8352(2) 0.33284(13) 0.0174(4) Uani d . 1 . .
H H12 1.3242 0.8321 0.2755 0.021 Uiso calc R 1 . .
C C13 1.6204(3) 0.8849(2) 0.34864(12) 0.0149(4) Uani d . 1 . .
C C14 1.7277(3) 0.8905(2) 0.43096(13) 0.0162(4) Uani d . 1 . .
H H14 1.8844 0.9243 0.4396 0.019 Uiso calc R 1 . .
C C15 1.6016(3) 0.8457(2) 0.50049(12) 0.0146(4) Uani d . 1 . .
H H15 1.6720 0.8492 0.5576 0.017 Uiso calc R 1 . .
C C16 1.3332(3) 0.7615(2) 0.91374(13) 0.0189(4) Uani d . 1 . .
H H16 1.1851 0.7146 0.9246 0.023 Uiso calc R 1 . .
C C17 1.4910(3) 0.8068(2) 0.98487(13) 0.0219(4) Uani d . 1 . .
H H17 1.4524 0.7913 1.0435 0.026 Uiso calc R 1 . .
C C18 1.7074(3) 0.8753(2) 0.96950(14) 0.0210(4) Uani d . 1 . .
H H18 1.8197 0.9079 1.0175 0.025 Uiso calc R 1 . .
C C19 1.7569(3) 0.8955(2) 0.88305(13) 0.0189(4) Uani d . 1 . .
H H19 1.9041 0.9416 0.8707 0.023 Uiso calc R 1 . .
C C20 1.5893(3) 0.8476(2) 0.81504(13) 0.0161(4) Uani d . 1 . .
H H20 1.6239 0.8625 0.7559 0.019 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 . . 93.57(6) ?
O1 Cu1 O3 . . 174.58(6) ?
N1 Cu1 O3 . . 81.17(6) ?
O1 Cu1 N4 . . 92.67(6) ?
N1 Cu1 N4 . . 172.51(7) ?
O3 Cu1 N4 . . 92.68(6) ?
C7 N1 N2 . . 117.25(16) ?
C7 N1 Cu1 . . 127.41(13) ?
N2 N1 Cu1 . . 115.34(12) ?
C9 N2 N1 . . 108.05(15) ?
O5 N3 O4 . . 123.25(17) ?
O5 N3 C13 . . 118.27(16) ?
O4 N3 C13 . . 118.47(17) ?
C20 N4 C16 . . 117.86(17) ?
C20 N4 Cu1 . . 121.38(13) ?
C16 N4 Cu1 . . 120.64(14) ?
C1 O1 Cu1 . . 127.54(12) ?
C3 O2 C8 . . 117.33(15) ?
C9 O3 Cu1 . . 110.23(12) ?
O1 C1 C2 . . 118.11(17) ?
O1 C1 C6 . . 124.11(17) ?
C2 C1 C6 . . 117.78(17) ?
C3 C2 C1 . . 121.55(17) ?
C3 C2 H2 . . 119.2 ?
C1 C2 H2 . . 119.2 ?
O2 C3 C2 . . 115.33(17) ?
O2 C3 C4 . . 123.65(18) ?
C2 C3 C4 . . 121.01(18) ?
C5 C4 C3 . . 118.12(18) ?
C5 C4 H4 . . 120.9 ?
C3 C4 H4 . . 120.9 ?
C4 C5 C6 . . 122.53(17) ?
C4 C5 H5 . . 118.7 ?
C6 C5 H5 . . 118.7 ?
C5 C6 C1 . . 119.00(17) ?
C5 C6 C7 . . 117.98(17) ?
C1 C6 C7 . . 123.02(17) ?
N1 C7 C6 . . 124.30(17) ?
N1 C7 H7 . . 117.9 ?
C6 C7 H7 . . 117.9 ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O3 C9 N2 . . 125.19(17) ?
O3 C9 C10 . . 117.01(17) ?
N2 C9 C10 . . 117.79(16) ?
C15 C10 C11 . . 119.71(17) ?
C15 C10 C9 . . 119.31(16) ?
C11 C10 C9 . . 120.98(18) ?
C12 C11 C10 . . 120.41(18) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C11 C12 C13 . . 118.53(17) ?
C11 C12 H12 . . 120.7 ?
C13 C12 H12 . . 120.7 ?
C12 C13 C14 . . 122.62(18) ?
C12 C13 N3 . . 119.26(17) ?
C14 C13 N3 . . 118.12(18) ?
C15 C14 C13 . . 118.62(18) ?
C15 C14 H14 . . 120.7 ?
C13 C14 H14 . . 120.7 ?
C14 C15 C10 . . 120.11(17) ?
C14 C15 H15 . . 119.9 ?
C10 C15 H15 . . 119.9 ?
N4 C16 C17 . . 122.91(19) ?
N4 C16 H16 . . 118.5 ?
C17 C16 H16 . . 118.5 ?
C16 C17 C18 . . 118.84(19) ?
C16 C17 H17 . . 120.6 ?
C18 C17 H17 . . 120.6 ?
C19 C18 C17 . . 118.81(19) ?
C19 C18 H18 . . 120.6 ?
C17 C18 H18 . . 120.6 ?
C20 C19 C18 . . 119.05(19) ?
C20 C19 H19 . . 120.5 ?
C18 C19 H19 . . 120.5 ?
N4 C20 C19 . . 122.52(18) ?
N4 C20 H20 . . 118.7 ?
C19 C20 H20 . . 118.7 ?
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 . 1.8922(14) ?
Cu1 N1 . 1.9239(16) ?
Cu1 O3 . 1.9320(14) ?
Cu1 N4 . 1.9989(16) ?
N1 C7 . 1.293(3) ?
N1 N2 . 1.399(2) ?
N2 C9 . 1.312(3) ?
N3 O5 . 1.229(2) ?
N3 O4 . 1.227(2) ?
N3 C13 . 1.467(2) ?
N4 C20 . 1.343(3) ?
N4 C16 . 1.347(2) ?
O1 C1 . 1.316(2) ?
O2 C3 . 1.363(2) ?
O2 C8 . 1.427(2) ?
O3 C9 . 1.299(2) ?
C1 C2 . 1.403(3) ?
C1 C6 . 1.434(3) ?
C2 C3 . 1.385(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.405(3) ?
C4 C5 . 1.380(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.404(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.435(3) ?
C7 H7 . 0.9500 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.485(3) ?
C10 C15 . 1.397(3) ?
C10 C11 . 1.403(3) ?
C11 C12 . 1.382(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.381(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.385(3) ?
C14 C15 . 1.387(3) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 C17 . 1.375(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.386(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.384(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.381(3) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 Cu1 N1 C7 . . . . 1.77(18) ?
O3 Cu1 N1 C7 . . . . -179.56(18) ?
O1 Cu1 N1 N2 . . . . -178.07(13) ?
O3 Cu1 N1 N2 . . . . 0.60(12) ?
C7 N1 N2 C9 . . . . -179.91(17) ?
Cu1 N1 N2 C9 . . . . -0.05(19) ?
O1 Cu1 N4 C20 . . . . 174.53(15) ?
O3 Cu1 N4 C20 . . . . -4.54(15) ?
O1 Cu1 N4 C16 . . . . -1.39(16) ?
O3 Cu1 N4 C16 . . . . 179.54(15) ?
N1 Cu1 O1 C1 . . . . -2.34(16) ?
N4 Cu1 O1 C1 . . . . 173.51(16) ?
N1 Cu1 O3 C9 . . . . -1.01(12) ?
N4 Cu1 O3 C9 . . . . -176.72(13) ?
Cu1 O1 C1 C2 . . . . -178.09(13) ?
Cu1 O1 C1 C6 . . . . 1.7(3) ?
O1 C1 C2 C3 . . . . 178.63(17) ?
C6 C1 C2 C3 . . . . -1.1(3) ?
C8 O2 C3 C2 . . . . -178.07(18) ?
C8 O2 C3 C4 . . . . 2.8(3) ?
C1 C2 C3 O2 . . . . -178.47(17) ?
C1 C2 C3 C4 . . . . 0.7(3) ?
O2 C3 C4 C5 . . . . 179.17(17) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . -0.4(3) ?
C4 C5 C6 C1 . . . . -0.1(3) ?
C4 C5 C6 C7 . . . . -179.44(17) ?
O1 C1 C6 C5 . . . . -178.95(17) ?
C2 C1 C6 C5 . . . . 0.8(3) ?
O1 C1 C6 C7 . . . . 0.4(3) ?
C2 C1 C6 C7 . . . . -179.86(17) ?
N2 N1 C7 C6 . . . . 179.34(16) ?
Cu1 N1 C7 C6 . . . . -0.5(3) ?
C5 C6 C7 N1 . . . . 178.35(18) ?
C1 C6 C7 N1 . . . . -1.0(3) ?
Cu1 O3 C9 N2 . . . . 1.5(2) ?
Cu1 O3 C9 C10 . . . . -177.59(12) ?
N1 N2 C9 O3 . . . . -1.0(3) ?
N1 N2 C9 C10 . . . . 178.08(15) ?
O3 C9 C10 C15 . . . . 9.0(3) ?
N2 C9 C10 C15 . . . . -170.09(17) ?
O3 C9 C10 C11 . . . . -170.48(17) ?
N2 C9 C10 C11 . . . . 10.4(3) ?
C15 C10 C11 C12 . . . . -0.4(3) ?
C9 C10 C11 C12 . . . . 179.15(17) ?
C10 C11 C12 C13 . . . . 0.1(3) ?
C11 C12 C13 C14 . . . . 0.4(3) ?
C11 C12 C13 N3 . . . . 179.37(17) ?
O5 N3 C13 C12 . . . . 174.64(18) ?
O4 N3 C13 C12 . . . . -5.6(3) ?
O5 N3 C13 C14 . . . . -6.3(3) ?
O4 N3 C13 C14 . . . . 173.44(18) ?
C12 C13 C14 C15 . . . . -0.6(3) ?
N3 C13 C14 C15 . . . . -179.62(16) ?
C13 C14 C15 C10 . . . . 0.4(3) ?
C11 C10 C15 C14 . . . . 0.1(3) ?
C9 C10 C15 C14 . . . . -179.40(17) ?
C20 N4 C16 C17 . . . . -0.1(3) ?
Cu1 N4 C16 C17 . . . . 175.93(16) ?
N4 C16 C17 C18 . . . . 0.0(3) ?
C16 C17 C18 C19 . . . . -0.1(3) ?
C17 C18 C19 C20 . . . . 0.4(3) ?
C16 N4 C20 C19 . . . . 0.4(3) ?
Cu1 N4 C20 C19 . . . . -175.60(15) ?
C18 C19 C20 N4 . . . . -0.6(3) ?
