##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2013-12-13
_journal_date_accepted     2014-01-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      3
_journal_page_first     o242
_journal_page_last     o242
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814001822
_journal_coeditor_code     FJ2657
_publ_contact_author_name     'M. Sithambaresan'
_publ_contact_author_address
;
Department of Chemistry
Faculty of Science
Eastern University
Chenkalady
Sri Lanka
;
_publ_contact_author_email     'eesans@yahoo.com'
_publ_contact_author_fax     '94-65-2240758'
_publ_contact_author_phone     '94-65-2240755'
_publ_section_title
;
N'-[(E)-Furan-2-ylmethylidene]-4-hydroxybenzohydrazide
;
loop_
    _publ_author_name
    _publ_author_address
    'Riya Datta'
;
      Department of Chemistry
      Christ University
      Hosur Road
      Bangalore 560 029
      India
;
    'V. Ramya'
;
      Department of Chemistry
      Christ University
      Hosur Road
      Bangalore 560 029
      India
;
    'M. Sithambaresan'
;
      Department of Chemistry
      Faculty of Science
      Eastern University, Sri Lanka
      Chenkalady
      Sri Lanka
;
    'M. R. Prathapachandra Kurup'
;
      Department of Applied Chemistry
      Cochin University of Science and Technology
      Kochi 682 022
      India
;
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 983574'
_chemical_name_systematic
;
N'-[(E)-Furan-2-ylmethylidene]-4-hydroxybenzohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H10 N2 O3'
_chemical_formula_sum     'C12 H10 N2 O3'
_chemical_formula_iupac     'C12 H10 N2 O3'
_chemical_formula_weight     230.22
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y+1/2, z'
    '-x+1/2, y+1/2, z+1/2'
_cell_length_a     9.5934(3)
_cell_length_b     11.1939(4)
_cell_length_c     10.3332(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1109.66(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     2.68
_cell_measurement_theta_max     28.36
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'light orange'
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.378
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     480
_exptl_absorpt_coefficient_mu     0.101
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2004)'
_exptl_absorpt_correction_T_min     0.9751
_exptl_absorpt_correction_T_max     0.9840
_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 APEXII CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     3425
_diffrn_reflns_av_R_equivalents     0.0154
_diffrn_reflns_av_sigmaI/netI     0.0147
_diffrn_reflns_theta_min     2.68
_diffrn_reflns_theta_max     24.99
_diffrn_reflns_theta_full     24.99
_diffrn_measured_fraction_theta_max     0.980
_diffrn_measured_fraction_theta_full     0.980
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_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 >
σ(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     1014
_reflns_number_gt     992
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0250
_refine_ls_R_factor_gt     0.0242
_refine_ls_wR_factor_gt     0.0634
_refine_ls_wR_factor_ref     0.0641
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.049
_refine_ls_number_reflns     1014
_refine_ls_number_parameters     163
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0363P)²+0.1774P] 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     0.131
_refine_diff_density_min     -0.103
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.046(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     ?
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     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'APEX2 and SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT and XPREP (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
          'ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010)'
_computing_publication_material
                        'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 1.10537(16) 0.44042(12) 0.85962(16) 0.0487(4) Uani d . 1 1 . .
    O O2 1.15292(13) 0.82491(12) 0.64988(16) 0.0454(4) Uani d . 1 1 . .
    O O3 0.79142(15) 1.25293(13) 0.43449(17) 0.0509(4) Uani d D 1 1 . .
    N N1 1.00354(16) 0.64857(13) 0.74734(17) 0.0346(4) Uani d . 1 1 . .
    N N2 0.94150(15) 0.74797(14) 0.69195(18) 0.0357(4) Uani d D 1 1 . .
    C C1 1.1354(3) 0.3230(2) 0.8813(3) 0.0609(7) Uani d . 1 1 . .
    H H1 1.2119 0.2956 0.9279 0.073 Uiso calc R 1 1 . .
    C C2 1.0401(3) 0.2529(2) 0.8265(3) 0.0655(7) Uani d . 1 1 . .
    H H2 1.0390 0.1698 0.8271 0.079 Uiso calc R 1 1 . .
    C C3 0.9410(3) 0.32850(19) 0.7673(3) 0.0528(6) Uani d . 1 1 . .
    H H3 0.8614 0.3054 0.7224 0.063 Uiso calc R 1 1 . .
    C C4 0.9853(2) 0.44092(17) 0.7889(2) 0.0394(5) Uani d . 1 1 . .
    C C5 0.9330(2) 0.55207(17) 0.7401(2) 0.0389(5) Uani d . 1 1 . .
    H H5 0.8452 0.5539 0.7019 0.047 Uiso calc R 1 1 . .
    C C6 1.02519(18) 0.83589(16) 0.64733(19) 0.0332(4) Uani d . 1 1 . .
    C C7 0.95845(19) 0.94475(16) 0.5952(2) 0.0327(4) Uani d . 1 1 . .
    C C8 0.81588(19) 0.96915(18) 0.6015(2) 0.0422(5) Uani d . 1 1 . .
    H H8 0.7566 0.9156 0.6428 0.051 Uiso calc R 1 1 . .
    C C9 0.7622(2) 1.07164(18) 0.5474(2) 0.0464(5) Uani d . 1 1 . .
    H H9 0.6670 1.0866 0.5525 0.056 Uiso calc R 1 1 . .
    C C10 0.8484(2) 1.15259(16) 0.48562(19) 0.0363(5) Uani d . 1 1 . .
    C C11 0.9907(2) 1.13042(17) 0.4805(2) 0.0400(5) Uani d . 1 1 . .
    H H11 1.0502 1.1850 0.4410 0.048 Uiso calc R 1 1 . .
    C C12 1.04335(19) 1.02759(17) 0.5340(2) 0.0383(5) Uani d . 1 1 . .
    H H12 1.1387 1.0131 0.5291 0.046 Uiso calc R 1 1 . .
    H H2' 0.8518(11) 0.7474(18) 0.676(2) 0.041(6) Uiso d D 1 1 . .
    H H3' 0.853(2) 1.288(2) 0.389(2) 0.062(8) Uiso d D 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    O1 C4 . 1.364(3) ?
    O1 C1 . 1.364(3) ?
    O2 C6 . 1.232(2) ?
    O3 C10 . 1.356(2) ?
    O3 H3' . 0.847(10) ?
    N1 C5 . 1.277(2) ?
    N1 N2 . 1.386(2) ?
    N2 C6 . 1.351(2) ?
    N2 H2' . 0.876(10) ?
    C1 C2 . 1.331(4) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.412(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.347(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.433(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.478(2) ?
    C7 C12 . 1.387(2) ?
    C7 C8 . 1.396(3) ?
    C8 C9 . 1.376(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.383(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.389(3) ?
    C11 C12 . 1.373(3) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 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
    C4 O1 C1 . . 105.67(19) ?
    C10 O3 H3' . . 108.7(18) ?
    C5 N1 N2 . . 115.31(16) ?
    C6 N2 N1 . . 118.08(14) ?
    C6 N2 H2' . . 121.6(14) ?
    N1 N2 H2' . . 119.6(14) ?
    C2 C1 O1 . . 110.7(2) ?
    C2 C1 H1 . . 124.7 ?
    O1 C1 H1 . . 124.7 ?
    C1 C2 C3 . . 107.1(2) ?
    C1 C2 H2 . . 126.5 ?
    C3 C2 H2 . . 126.5 ?
    C4 C3 C2 . . 106.0(2) ?
    C4 C3 H3 . . 127.0 ?
    C2 C3 H3 . . 127.0 ?
    C3 C4 O1 . . 110.59(19) ?
    C3 C4 C5 . . 129.9(2) ?
    O1 C4 C5 . . 119.19(18) ?
    N1 C5 C4 . . 121.89(19) ?
    N1 C5 H5 . . 119.1 ?
    C4 C5 H5 . . 119.1 ?
    O2 C6 N2 . . 120.73(17) ?
    O2 C6 C7 . . 121.39(16) ?
    N2 C6 C7 . . 117.87(15) ?
    C12 C7 C8 . . 117.77(17) ?
    C12 C7 C6 . . 117.59(15) ?
    C8 C7 C6 . . 124.63(17) ?
    C9 C8 C7 . . 120.71(19) ?
    C9 C8 H8 . . 119.6 ?
    C7 C8 H8 . . 119.6 ?
    C8 C9 C10 . . 120.64(17) ?
    C8 C9 H9 . . 119.7 ?
    C10 C9 H9 . . 119.7 ?
    O3 C10 C9 . . 118.77(17) ?
    O3 C10 C11 . . 121.97(18) ?
    C9 C10 C11 . . 119.24(18) ?
    C12 C11 C10 . . 119.74(18) ?
    C12 C11 H11 . . 120.1 ?
    C10 C11 H11 . . 120.1 ?
    C11 C12 C7 . . 121.88(16) ?
    C11 C12 H12 . . 119.1 ?
    C7 C12 H12 . . 119.1 ?
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
    C5 N1 N2 C6 . . . . -152.8(2) ?
    C4 O1 C1 C2 . . . . 0.4(3) ?
    O1 C1 C2 C3 . . . . -0.9(3) ?
    C1 C2 C3 C4 . . . . 1.0(3) ?
    C2 C3 C4 O1 . . . . -0.8(3) ?
    C2 C3 C4 C5 . . . . 173.0(2) ?
    C1 O1 C4 C3 . . . . 0.2(3) ?
    C1 O1 C4 C5 . . . . -174.3(2) ?
    N2 N1 C5 C4 . . . . 177.85(18) ?
    C3 C4 C5 N1 . . . . -164.8(3) ?
    O1 C4 C5 N1 . . . . 8.5(3) ?
    N1 N2 C6 O2 . . . . 3.7(3) ?
    N1 N2 C6 C7 . . . . -176.57(16) ?
    O2 C6 C7 C12 . . . . 8.1(3) ?
    N2 C6 C7 C12 . . . . -171.64(19) ?
    O2 C6 C7 C8 . . . . -172.9(2) ?
    N2 C6 C7 C8 . . . . 7.4(3) ?
    C12 C7 C8 C9 . . . . 0.7(3) ?
    C6 C7 C8 C9 . . . . -178.4(2) ?
    C7 C8 C9 C10 . . . . 0.0(4) ?
    C8 C9 C10 O3 . . . . -179.5(2) ?
    C8 C9 C10 C11 . . . . -1.1(3) ?
    O3 C10 C11 C12 . . . . 179.84(19) ?
    C9 C10 C11 C12 . . . . 1.5(3) ?
    C10 C11 C12 C7 . . . . -0.8(3) ?
    C8 C7 C12 C11 . . . . -0.3(3) ?
    C6 C7 C12 C11 . . . . 178.9(2) ?
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
    N2 H2' O2 3_465 0.876(10) 2.090(12) 2.9187(19) 157.4(18)
    O3 H3' N1 2_774 0.847(10) 2.134(12) 2.971(2) 169(3)
    C5 H5 O2 3_465 0.9300 2.35 3.160(2) 145
    C11 H11 O3 3_575 0.9300 2.42 3.202(2) 142
