##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-09-11
_journal_date_accepted     2007-09-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     10
_journal_page_first     o4153
_journal_page_last     o4153
_journal_paper_category     QO
_journal_coeditor_code     BT2506
_publ_contact_author_name     'Dr. Ke-Wei Lei'
_publ_contact_author_address
;
State Key Laboratory Base of Novel Functional Materials and Preparation Science
    Institute of solid Materials Chemistry
    Faculty of Materials Science and Chemical Engineering
    Ningbo University
    Ningbo 315211
    People's Republic of China
;
_publ_contact_author_email     leikeweipublic@hotmail.com
_publ_contact_author_fax     '86 574 87600791'
_publ_contact_author_phone     '86 574 87600791'
_publ_section_title
;
3-Hydroxy-N'-phenylnaphthalene-2-carbohydrazide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ke-Wei Lei' ?
;
State Key Laboratory Base of Novel Functional Materials and Preparation Science
    Institute of Solid Materials Chemistry
    Faculty of Materials Science and Chemical Engineering
    Ningbo University
    Ningbo 315211
    People's Republic of China
;
    'Hai-Mei Feng' ?
;
State Key Laboratory Base of Novel Functional Materials and Preparation Science
    Institute of Solid Materials Chemistry
    Faculty of Materials Science and Chemical Engineering
    Ningbo University
    Ningbo 315211
    People's Republic of China
;
    'Feng-Qing Li' ?
;
    School of Environmental and Biological Science and Technology
    Dalian University of Technology
    Dalian 116024
    People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-Hydroxy-N'-phenylnaphthalene-2-carbohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H14 N2 O3'
_chemical_formula_sum     'C18 H14 N2 O3'
_chemical_formula_weight     306.31
_chemical_melting_point     '219-223'
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     4.8473(10)
_cell_length_b     33.907(7)
_cell_length_c     8.9148(18)
_cell_angle_alpha     90.00
_cell_angle_beta     91.61(3)
_cell_angle_gamma     90.00
_cell_volume     1464.6(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8325
_cell_measurement_theta_min     6.01
_cell_measurement_theta_max     27.59
_cell_measurement_temperature     273(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.570
_exptl_crystal_size_mid     0.390
_exptl_crystal_size_min     0.310
_exptl_crystal_density_diffrn     1.389
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     640
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 1998)'
_exptl_absorpt_correction_T_min     0.936
_exptl_absorpt_correction_T_max     0.976
_exptl_special_details
;
;
_diffrn_ambient_temperature     273(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     'Rigaku R-AXIS RAPID'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     0
_diffrn_reflns_number     7743
_diffrn_reflns_av_R_equivalents     0.0685
_diffrn_reflns_av_sigmaI/netI     0.0529
_diffrn_reflns_theta_min     3.32
_diffrn_reflns_theta_max     27.59
_diffrn_reflns_theta_full     28.50
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -44
_diffrn_reflns_limit_k_max     44
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     .
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3401
_reflns_number_gt     2414
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0738
_refine_ls_R_factor_gt     0.0544
_refine_ls_wR_factor_gt     0.1109
_refine_ls_wR_factor_ref     0.1169
_refine_ls_goodness_of_fit_ref     1.032
_refine_ls_restrained_S_all     1.032
_refine_ls_number_reflns     3401
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0502P)²+0.5358P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.177
_refine_diff_density_min     -0.181
_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, 1998)'
_computing_cell_refinement     'SMART (Bruker, 1998)'
_computing_data_reduction     'SAINT (Bruker, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1998)'
_computing_publication_material     'SHELXTL (Bruker, 1998)'
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
    C C1 0.3553(9) 0.97519(9) 0.8154(4) 0.0902(12) Uani d . 1 . .
    H H1B 0.4486 0.9957 0.8639 0.108 Uiso calc R 1 . .
    C C2 0.0784(6) 0.91469(9) 0.6775(4) 0.0685(9) Uani d . 1 . .
    H H2B -0.0180 0.8943 0.6301 0.082 Uiso calc R 1 . .
    C C3 0.0072(7) 0.95336(11) 0.6456(4) 0.0884(11) Uani d . 1 . .
    H H3B -0.1360 0.9589 0.5773 0.106 Uiso calc R 1 . .
    C C4 0.1484(9) 0.98325(10) 0.7151(5) 0.0905(12) Uani d . 1 . .
    H H4A 0.1025 1.0093 0.6935 0.109 Uiso calc R 1 . .
    C C5 0.4286(7) 0.93649(8) 0.8464(4) 0.0707(9) Uani d . 1 . .
    H H5A 0.5734 0.9311 0.9140 0.085 Uiso calc R 1 . .
    C C6 0.2887(5) 0.90608(7) 0.7777(3) 0.0464(7) Uani d . 1 . .
    C C7 0.3757(5) 0.86499(7) 0.8103(3) 0.0435(6) Uani d . 1 . .
    C C8 0.1220(5) 0.76940(7) 0.7606(3) 0.0403(6) Uani d . 1 . .
    C C9 0.2169(5) 0.72870(7) 0.7964(3) 0.0385(6) Uani d . 1 . .
    C C10 0.5067(5) 0.68088(7) 0.9256(3) 0.0469(7) Uani d . 1 . .
    H H10A 0.6467 0.6752 0.9957 0.056 Uiso calc R 1 . .
    C C11 0.4322(5) 0.71903(7) 0.9015(3) 0.0417(6) Uani d . 1 . .
    C C12 0.0889(5) 0.69841(7) 0.7208(3) 0.0454(7) Uani d . 1 . .
    H H12A -0.0537 0.7044 0.6527 0.054 Uiso calc R 1 . .
    C C13 0.1627(5) 0.65876(7) 0.7414(3) 0.0431(6) Uani d . 1 . .
    C C14 0.3760(5) 0.64988(7) 0.8464(3) 0.0457(7) Uani d . 1 . .
    C C15 0.4518(6) 0.60999(8) 0.8667(4) 0.0624(8) Uani d . 1 . .
    H H15A 0.5928 0.6036 0.9353 0.075 Uiso calc R 1 . .
    C C16 0.0314(6) 0.62774(8) 0.6613(3) 0.0576(8) Uani d . 1 . .
    H H16A -0.1112 0.6333 0.5927 0.069 Uiso calc R 1 . .
    C C17 0.1121(6) 0.58983(8) 0.6841(3) 0.0638(8) Uani d . 1 . .
    H H17A 0.0261 0.5696 0.6299 0.077 Uiso calc R 1 . .
    C C18 0.3226(6) 0.58093(8) 0.7879(4) 0.0673(9) Uani d . 1 . .
    H H18A 0.3750 0.5548 0.8033 0.081 Uiso calc R 1 . .
    O O1 0.6144(3) 0.85645(5) 0.8467(2) 0.0635(6) Uani d . 1 . .
    O O2 -0.0689(4) 0.77662(5) 0.6712(2) 0.0607(6) Uani d . 1 . .
    O O3 0.5609(3) 0.74934(5) 0.9766(2) 0.0548(5) Uani d . 1 . .
    H H3A 0.6758 0.7404 1.0367 0.082 Uiso calc R 1 . .
    N N1 0.1807(4) 0.83749(6) 0.7983(2) 0.0471(6) Uani d . 1 . .
    H H1A 0.0145 0.8436 0.7710 0.056 Uiso calc R 1 . .
    N N2 0.2512(4) 0.79894(6) 0.8305(2) 0.0474(6) Uani d . 1 . .
    H H2A 0.3797 0.7940 0.8963 0.057 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.135(3) 0.045(2) 0.090(3) -0.012(2) 0.001(3) -0.0035(19)
    C2 0.0663(19) 0.0537(18) 0.085(2) -0.0009(15) -0.0127(18) 0.0181(16)
    C3 0.086(2) 0.068(2) 0.110(3) 0.012(2) -0.015(2) 0.032(2)
    C4 0.119(3) 0.054(2) 0.100(3) 0.021(2) 0.020(3) 0.020(2)
    C5 0.083(2) 0.0514(19) 0.077(2) -0.0081(17) -0.0127(18) 0.0005(16)
    C6 0.0409(15) 0.0427(15) 0.0557(18) 0.0002(12) 0.0008(14) 0.0035(13)
    C7 0.0352(15) 0.0459(15) 0.0488(16) -0.0003(13) -0.0062(12) -0.0019(12)
    C8 0.0356(13) 0.0444(15) 0.0404(15) -0.0007(12) -0.0094(13) -0.0014(12)
    C9 0.0350(13) 0.0407(14) 0.0394(15) 0.0005(11) -0.0060(12) 0.0016(12)
    C10 0.0439(14) 0.0448(16) 0.0511(16) 0.0045(12) -0.0141(13) 0.0051(13)
    C11 0.0411(14) 0.0410(15) 0.0424(15) -0.0030(12) -0.0070(12) -0.0020(12)
    C12 0.0426(15) 0.0472(16) 0.0457(16) -0.0019(12) -0.0101(13) 0.0019(13)
    C13 0.0447(15) 0.0402(15) 0.0443(15) -0.0039(12) 0.0011(13) -0.0016(12)
    C14 0.0426(15) 0.0427(15) 0.0518(16) 0.0031(12) -0.0001(13) 0.0031(13)
    C15 0.0633(19) 0.0454(17) 0.078(2) 0.0051(14) -0.0099(16) 0.0045(15)
    C16 0.0643(19) 0.0491(18) 0.0589(18) -0.0085(14) -0.0060(15) -0.0029(14)
    C17 0.072(2) 0.0476(18) 0.072(2) -0.0113(15) 0.0003(18) -0.0118(15)
    C18 0.074(2) 0.0413(16) 0.087(2) 0.0031(16) 0.0009(19) -0.0037(16)
    O1 0.0357(10) 0.0544(12) 0.0995(17) 0.0012(9) -0.0154(10) 0.0020(11)
    O2 0.0610(12) 0.0479(11) 0.0709(14) 0.0019(9) -0.0377(11) -0.0008(9)
    O3 0.0550(11) 0.0443(10) 0.0634(12) 0.0041(9) -0.0303(10) 0.0009(9)
    N1 0.0340(11) 0.0389(12) 0.0673(15) 0.0032(10) -0.0172(10) 0.0033(11)
    N2 0.0442(12) 0.0371(12) 0.0593(14) 0.0040(10) -0.0249(11) 0.0021(11)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1 C4 . 1.352(5) ?
    C1 C5 . 1.385(4) ?
    C1 H1B . 0.9300 ?
    C2 C6 . 1.368(4) ?
    C2 C3 . 1.383(4) ?
    C2 H2B . 0.9300 ?
    C3 C4 . 1.362(5) ?
    C3 H3B . 0.9300 ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.369(4) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.482(3) ?
    C7 O1 . 1.227(3) ?
    C7 N1 . 1.330(3) ?
    C8 O2 . 1.229(3) ?
    C8 N2 . 1.327(3) ?
    C8 C9 . 1.487(3) ?
    C9 C12 . 1.367(3) ?
    C9 C11 . 1.421(3) ?
    C10 C11 . 1.358(3) ?
    C10 C14 . 1.407(3) ?
    C10 H10A . 0.9300 ?
    C11 O3 . 1.368(3) ?
    C12 C13 . 1.402(3) ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.408(4) ?
    C13 C16 . 1.413(4) ?
    C14 C15 . 1.412(4) ?
    C15 C18 . 1.353(4) ?
    C15 H15A . 0.9300 ?
    C16 C17 . 1.357(4) ?
    C16 H16A . 0.9300 ?
    C17 C18 . 1.392(4) ?
    C17 H17A . 0.9300 ?
    C18 H18A . 0.9300 ?
    O3 H3A . 0.8200 ?
    N1 N2 . 1.379(3) ?
    N1 H1A . 0.8600 ?
    N2 H2A . 0.8600 ?
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
    C4 C1 C5 . . 120.3(3) ?
    C4 C1 H1B . . 119.8 ?
    C5 C1 H1B . . 119.8 ?
    C6 C2 C3 . . 120.9(3) ?
    C6 C2 H2B . . 119.6 ?
    C3 C2 H2B . . 119.6 ?
    C4 C3 C2 . . 119.5(3) ?
    C4 C3 H3B . . 120.2 ?
    C2 C3 H3B . . 120.2 ?
    C1 C4 C3 . . 120.3(3) ?
    C1 C4 H4A . . 119.9 ?
    C3 C4 H4A . . 119.9 ?
    C6 C5 C1 . . 120.2(3) ?
    C6 C5 H5A . . 119.9 ?
    C1 C5 H5A . . 119.9 ?
    C2 C6 C5 . . 118.8(3) ?
    C2 C6 C7 . . 122.1(2) ?
    C5 C6 C7 . . 119.0(2) ?
    O1 C7 N1 . . 121.2(2) ?
    O1 C7 C6 . . 122.3(2) ?
    N1 C7 C6 . . 116.4(2) ?
    O2 C8 N2 . . 119.4(2) ?
    O2 C8 C9 . . 123.1(2) ?
    N2 C8 C9 . . 117.4(2) ?
    C12 C9 C11 . . 117.8(2) ?
    C12 C9 C8 . . 117.3(2) ?
    C11 C9 C8 . . 124.9(2) ?
    C11 C10 C14 . . 121.2(2) ?
    C11 C10 H10A . . 119.4 ?
    C14 C10 H10A . . 119.4 ?
    C10 C11 O3 . . 121.5(2) ?
    C10 C11 C9 . . 120.7(2) ?
    O3 C11 C9 . . 117.8(2) ?
    C9 C12 C13 . . 123.0(2) ?
    C9 C12 H12A . . 118.5 ?
    C13 C12 H12A . . 118.5 ?
    C12 C13 C14 . . 118.2(2) ?
    C12 C13 C16 . . 122.6(2) ?
    C14 C13 C16 . . 119.3(2) ?
    C10 C14 C13 . . 119.1(2) ?
    C10 C14 C15 . . 122.7(2) ?
    C13 C14 C15 . . 118.3(2) ?
    C18 C15 C14 . . 121.1(3) ?
    C18 C15 H15A . . 119.5 ?
    C14 C15 H15A . . 119.5 ?
    C17 C16 C13 . . 120.4(3) ?
    C17 C16 H16A . . 119.8 ?
    C13 C16 H16A . . 119.8 ?
    C16 C17 C18 . . 120.5(3) ?
    C16 C17 H17A . . 119.7 ?
    C18 C17 H17A . . 119.7 ?
    C15 C18 C17 . . 120.5(3) ?
    C15 C18 H18A . . 119.8 ?
    C17 C18 H18A . . 119.8 ?
    C11 O3 H3A . . 109.5 ?
    C7 N1 N2 . . 118.4(2) ?
    C7 N1 H1A . . 120.8 ?
    N2 N1 H1A . . 120.8 ?
    C8 N2 N1 . . 120.4(2) ?
    C8 N2 H2A . . 119.8 ?
    N1 N2 H2A . . 119.8 ?
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
    N1 H1A O1 1_455 0.8600 2.1200 2.864(3) 145.00 yes
    N2 H2A O3 . 0.8600 1.8800 2.582(3) 138.00 yes
    O3 H3A O2 4_676 0.8200 1.7900 2.613(3) 177.00 yes
