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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-10-21
_journal_date_accepted     2009-10-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     12
_journal_page_first     o2978
_journal_page_last     o2978
_journal_paper_category     QO
_journal_coeditor_code     BH2256
_publ_contact_author_name     'De-Suo Yang'
_publ_contact_author_address
;
Department of Chemistry and Chemical Engineering
Baoji University of Arts and Sciences
Baoji 721007
People's Republic of China
;
_publ_contact_author_email     desuoyang@yahoo.com.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
3-Hydroxy-N'-(5-hydroxy-2-nitrobenzylidene)-2-naphthohydrazide
;
loop_
    _publ_author_name
    _publ_author_address
    "Yang, De-Suo"
;
Department of Chemistry and Chemical Engineering
Baoji University of Arts and Sciences
Baoji 721007
People's Republic of China
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-Hydroxy-N'-(5-hydroxy-2-nitrobenzylidene)-2-naphthohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H13 N3 O5'
_chemical_formula_sum     'C18 H13 N3 O5'
_chemical_formula_iupac     'C18 H13 N3 O5'
_chemical_formula_weight     351.31
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     10.1588(3)
_cell_length_b     8.2562(2)
_cell_length_c     19.5268(5)
_cell_angle_alpha     90.00
_cell_angle_beta     104.8670(10)
_cell_angle_gamma     90.00
_cell_volume     1582.95(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2463
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     26.6
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.23
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.474
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     728
_exptl_absorpt_coefficient_mu     0.110
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9751
_exptl_absorpt_correction_T_max     0.9783
_exptl_special_details     ?
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9168
_diffrn_reflns_av_R_equivalents     0.0278
_diffrn_reflns_av_sigmaI/netI     0.0282
_diffrn_reflns_theta_min     2.08
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details     ?
_reflns_number_total     3425
_reflns_number_gt     2436
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0639
_refine_ls_R_factor_gt     0.0439
_refine_ls_wR_factor_gt     0.1070
_refine_ls_wR_factor_ref     0.1187
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     3425
_refine_ls_number_parameters     241
_refine_ls_number_restraints     1
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0503P)²+0.3232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.185
_refine_diff_density_min     -0.193
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 2002)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT (Bruker, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    N N1 0.88109(14) 0.92607(17) 0.05530(7) 0.0462(4) Uani d D 1 . .
    N N2 1.00455(13) 0.88709(16) 0.10140(7) 0.0446(3) Uani d . 1 . .
    N N3 1.20940(14) 0.48961(18) 0.04801(7) 0.0461(3) Uani d . 1 . .
    O O1 0.86564(13) 1.16125(15) 0.11112(6) 0.0575(4) Uani d . 1 . .
    O O2 0.63397(15) 1.31345(18) 0.08033(7) 0.0689(4) Uani d . 1 . .
    H H2 0.7084 1.2854 0.1052 0.103 Uiso calc R 1 . .
    O O3 1.13711(14) 0.56430(16) -0.00173(6) 0.0612(4) Uani d . 1 . .
    O O4 1.24674(14) 0.34954(16) 0.04217(7) 0.0695(4) Uani d . 1 . .
    O O5 1.38574(15) 0.75885(19) 0.31532(6) 0.0721(4) Uani d . 1 . .
    H H5 1.4565 0.7160 0.3377 0.108 Uiso calc R 1 . .
    C C1 0.69456(16) 1.10569(19) 0.00579(8) 0.0407(4) Uani d . 1 . .
    C C2 0.60609(17) 1.2299(2) 0.01840(9) 0.0485(4) Uani d . 1 . .
    C C3 0.49048(18) 1.2674(3) -0.03235(10) 0.0601(5) Uani d . 1 . .
    H H3 0.4332 1.3482 -0.0234 0.072 Uiso calc R 1 . .
    C C4 0.45611(17) 1.1865(3) -0.09781(10) 0.0582(5) Uani d . 1 . .
    C C5 0.3359(2) 1.2237(3) -0.15133(13) 0.0833(8) Uani d . 1 . .
    H H5A 0.2756 1.3013 -0.1428 0.100 Uiso calc R 1 . .
    C C6 0.3090(3) 1.1465(4) -0.21477(15) 0.1025(11) Uani d . 1 . .
    H H6 0.2299 1.1717 -0.2493 0.123 Uiso calc R 1 . .
    C C7 0.3980(3) 1.0294(3) -0.22928(13) 0.1001(10) Uani d . 1 . .
    H H7 0.3782 0.9787 -0.2733 0.120 Uiso calc R 1 . .
    C C8 0.5134(2) 0.9896(3) -0.17908(11) 0.0769(7) Uani d . 1 . .
    H H8 0.5721 0.9116 -0.1889 0.092 Uiso calc R 1 . .
    C C9 0.54456(19) 1.0664(2) -0.11211(9) 0.0541(5) Uani d . 1 . .
    C C10 0.66309(18) 1.0299(2) -0.05915(9) 0.0477(4) Uani d . 1 . .
    H H10 0.7224 0.9519 -0.0683 0.057 Uiso calc R 1 . .
    C C11 0.81986(16) 1.06728(19) 0.06131(8) 0.0417(4) Uani d . 1 . .
    C C12 1.04643(17) 0.7455(2) 0.09371(9) 0.0468(4) Uani d . 1 . .
    H H12 0.9935 0.6774 0.0596 0.056 Uiso calc R 1 . .
    C C13 1.17752(16) 0.68736(18) 0.13789(8) 0.0398(4) Uani d . 1 . .
    C C14 1.25482(16) 0.56598(18) 0.11681(8) 0.0381(3) Uani d . 1 . .
    C C15 1.37767(16) 0.51385(19) 0.16009(9) 0.0429(4) Uani d . 1 . .
    H H15 1.4276 0.4342 0.1443 0.051 Uiso calc R 1 . .
    C C16 1.42572(16) 0.5796(2) 0.22626(8) 0.0440(4) Uani d . 1 . .
    H H16 1.5094 0.5471 0.2550 0.053 Uiso calc R 1 . .
    C C17 1.34847(18) 0.6951(2) 0.24990(8) 0.0466(4) Uani d . 1 . .
    C C18 1.22688(17) 0.7487(2) 0.20549(8) 0.0481(4) Uani d . 1 . .
    H H18 1.1772 0.8280 0.2216 0.058 Uiso calc R 1 . .
    H H1 0.8395(18) 0.8513(19) 0.0237(8) 0.066(6) Uiso d D 1 . .
_geom_special_details     ?
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
    N1 C11 . 1.341(2) ?
    N1 N2 . 1.3812(18) ?
    N1 H1 . 0.898(9) ?
    N2 C12 . 1.266(2) ?
    N3 O3 . 1.2235(18) ?
    N3 O4 . 1.2315(18) ?
    N3 C14 . 1.448(2) ?
    O1 C11 . 1.2378(18) ?
    O2 C2 . 1.357(2) ?
    O2 H2 . 0.8200 ?
    O5 C17 . 1.343(2) ?
    O5 H5 . 0.8200 ?
    C1 C10 . 1.376(2) ?
    C1 C2 . 1.426(2) ?
    C1 C11 . 1.479(2) ?
    C2 C3 . 1.364(2) ?
    C3 C4 . 1.405(3) ?
    C3 H3 . 0.9300 ?
    C4 C9 . 1.414(3) ?
    C4 C5 . 1.422(3) ?
    C5 C6 . 1.357(4) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.402(4) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.362(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.414(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.404(2) ?
    C10 H10 . 0.9300 ?
    C12 C13 . 1.469(2) ?
    C12 H12 . 0.9300 ?
    C13 C18 . 1.382(2) ?
    C13 C14 . 1.399(2) ?
    C14 C15 . 1.384(2) ?
    C15 C16 . 1.371(2) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.387(2) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.387(2) ?
    C18 H18 . 0.9300 ?
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
    C11 N1 N2 . . 120.64(13) ?
    C11 N1 H1 . . 120.7(13) ?
    N2 N1 H1 . . 118.4(13) ?
    C12 N2 N1 . . 114.48(14) ?
    O3 N3 O4 . . 122.43(14) ?
    O3 N3 C14 . . 120.03(14) ?
    O4 N3 C14 . . 117.54(14) ?
    C2 O2 H2 . . 109.5 ?
    C17 O5 H5 . . 109.5 ?
    C10 C1 C2 . . 118.58(15) ?
    C10 C1 C11 . . 122.05(15) ?
    C2 C1 C11 . . 119.31(14) ?
    O2 C2 C3 . . 118.43(17) ?
    O2 C2 C1 . . 121.50(15) ?
    C3 C2 C1 . . 120.07(17) ?
    C2 C3 C4 . . 121.34(18) ?
    C2 C3 H3 . . 119.3 ?
    C4 C3 H3 . . 119.3 ?
    C3 C4 C9 . . 119.42(16) ?
    C3 C4 C5 . . 122.1(2) ?
    C9 C4 C5 . . 118.4(2) ?
    C6 C5 C4 . . 120.2(3) ?
    C6 C5 H5A . . 119.9 ?
    C4 C5 H5A . . 119.9 ?
    C5 C6 C7 . . 121.3(2) ?
    C5 C6 H6 . . 119.4 ?
    C7 C6 H6 . . 119.4 ?
    C8 C7 C6 . . 120.1(3) ?
    C8 C7 H7 . . 119.9 ?
    C6 C7 H7 . . 119.9 ?
    C7 C8 C9 . . 120.3(3) ?
    C7 C8 H8 . . 119.8 ?
    C9 C8 H8 . . 119.8 ?
    C10 C9 C4 . . 118.26(17) ?
    C10 C9 C8 . . 122.1(2) ?
    C4 C9 C8 . . 119.63(18) ?
    C1 C10 C9 . . 122.28(17) ?
    C1 C10 H10 . . 118.9 ?
    C9 C10 H10 . . 118.9 ?
    O1 C11 N1 . . 121.64(14) ?
    O1 C11 C1 . . 121.38(15) ?
    N1 C11 C1 . . 116.98(14) ?
    N2 C12 C13 . . 120.90(15) ?
    N2 C12 H12 . . 119.5 ?
    C13 C12 H12 . . 119.5 ?
    C18 C13 C14 . . 116.75(14) ?
    C18 C13 C12 . . 119.55(15) ?
    C14 C13 C12 . . 123.64(14) ?
    C15 C14 C13 . . 121.96(14) ?
    C15 C14 N3 . . 116.99(14) ?
    C13 C14 N3 . . 121.04(14) ?
    C16 C15 C14 . . 119.98(15) ?
    C16 C15 H15 . . 120.0 ?
    C14 C15 H15 . . 120.0 ?
    C15 C16 C17 . . 119.39(15) ?
    C15 C16 H16 . . 120.3 ?
    C17 C16 H16 . . 120.3 ?
    O5 C17 C16 . . 122.72(15) ?
    O5 C17 C18 . . 117.25(16) ?
    C16 C17 C18 . . 120.03(15) ?
    C13 C18 C17 . . 121.79(16) ?
    C13 C18 H18 . . 119.1 ?
    C17 C18 H18 . . 119.1 ?
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
    _geom_hbond_publ_flag
    O2 H2 O1 . 0.82 1.88 2.5987(18) 146.3 yes
    N1 H1 O4 3_765 0.898(9) 2.144(10) 3.0361(19) 172.8(18) yes
    O5 H5 O1 2_745 0.82 1.88 2.6889(17) 168.0 yes
