##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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     SHELXL-97
_journal_date_recd_electronic     2008-04-22
_journal_date_accepted     2008-04-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      6
_journal_page_first     o961
_journal_page_last     o961
_journal_paper_category     QO
_journal_coeditor_code     SG2239
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
(2,4-Dimethoxybenzylidene)-2-hydroxybenzohydrazide ethanol solvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Yehye, Wagee A.'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Ariffin, Azhar'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(2,4-Dimethoxybenzylidene)-2-hydroxybenzohydrazide ethanol solvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H16 N2 O4, C2 H6 O'
_chemical_formula_sum     'C18 H22 N2 O5'
_chemical_formula_iupac     'C16 H16 N2 O4, C2 H6 O'
_chemical_formula_weight     346.38
_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     7.7909(2)
_cell_length_b     18.0539(6)
_cell_length_c     12.0001(4)
_cell_angle_alpha     90.00
_cell_angle_beta     93.803(2)
_cell_angle_gamma     90.00
_cell_volume     1684.17(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1895
_cell_measurement_theta_min     2.8
_cell_measurement_theta_max     25.5
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.366
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     736
_exptl_absorpt_coefficient_mu     0.100
_exptl_absorpt_correction_type     None
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     100(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 APEX'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13796
_diffrn_reflns_av_R_equivalents     0.0590
_diffrn_reflns_av_sigmaI/netI     0.0629
_diffrn_reflns_theta_min     2.04
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3853
_reflns_number_gt     2575
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0789
_refine_ls_R_factor_gt     0.0461
_refine_ls_wR_factor_gt     0.1015
_refine_ls_wR_factor_ref     0.1179
_refine_ls_goodness_of_fit_ref     1.032
_refine_ls_restrained_S_all     1.032
_refine_ls_number_reflns     3853
_refine_ls_number_parameters     241
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0476P)²+0.175P] 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     0.211
_refine_diff_density_min     -0.245
_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     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 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
    O O1 0.64682(15) 0.22307(7) 0.69448(11) 0.0248(3) Uani d D 1 . .
    O O2 0.48542(15) 0.30514(7) 0.55256(10) 0.0253(3) Uani d . 1 . .
    O O3 0.09164(14) 0.62457(7) 0.44328(10) 0.0224(3) Uani d . 1 . .
    O O4 -0.15888(16) 0.55131(7) 0.07909(10) 0.0280(3) Uani d . 1 . .
    O O5 0.45339(16) 0.56902(7) 0.68732(11) 0.0256(3) Uani d D 1 . .
    N N1 0.40917(17) 0.42200(9) 0.59366(12) 0.0191(3) Uani d D 1 . .
    N N2 0.32044(17) 0.42928(8) 0.48948(11) 0.0195(3) Uani d . 1 . .
    C C1 0.6546(2) 0.28297(10) 0.76338(14) 0.0199(4) Uani d . 1 . .
    C C2 0.7381(2) 0.27412(10) 0.86870(14) 0.0219(4) Uani d . 1 . .
    H H2 0.7858 0.2275 0.8904 0.026 Uiso calc R 1 . .
    C C3 0.7514(2) 0.33316(11) 0.94120(14) 0.0231(4) Uani d . 1 . .
    H H3 0.8073 0.3266 1.0133 0.028 Uiso calc R 1 . .
    C C4 0.6847(2) 0.40220(10) 0.91101(14) 0.0230(4) Uani d . 1 . .
    H H4 0.6962 0.4428 0.9614 0.028 Uiso calc R 1 . .
    C C5 0.6014(2) 0.41094(10) 0.80671(14) 0.0211(4) Uani d . 1 . .
    H H5 0.5560 0.4581 0.7856 0.025 Uiso calc R 1 . .
    C C6 0.5825(2) 0.35172(10) 0.73132(14) 0.0180(4) Uani d . 1 . .
    C C7 0.4908(2) 0.35796(10) 0.61929(14) 0.0192(4) Uani d . 1 . .
    C C8 0.22902(19) 0.48872(10) 0.47864(14) 0.0188(4) Uani d . 1 . .
    H H8 0.2277 0.5226 0.5391 0.023 Uiso calc R 1 . .
    C C9 0.1282(2) 0.50446(10) 0.37526(14) 0.0185(4) Uani d . 1 . .
    C C10 0.0552(2) 0.57510(10) 0.35888(14) 0.0189(4) Uani d . 1 . .
    C C11 -0.0433(2) 0.59274(10) 0.26156(14) 0.0197(4) Uani d . 1 . .
    H H11 -0.0930 0.6405 0.2519 0.024 Uiso calc R 1 . .
    C C12 -0.0677(2) 0.53942(10) 0.17899(14) 0.0213(4) Uani d . 1 . .
    C C13 0.0016(2) 0.46857(10) 0.19353(15) 0.0227(4) Uani d . 1 . .
    H H13 -0.0173 0.4321 0.1369 0.027 Uiso calc R 1 . .
    C C14 0.0973(2) 0.45200(10) 0.29057(14) 0.0205(4) Uani d . 1 . .
    H H14 0.1438 0.4036 0.3004 0.025 Uiso calc R 1 . .
    C C15 0.0125(2) 0.69592(10) 0.43449(15) 0.0240(4) Uani d . 1 . .
    H H15A 0.0456 0.7250 0.5015 0.036 Uiso calc R 1 . .
    H H15B -0.1128 0.6902 0.4275 0.036 Uiso calc R 1 . .
    H H15C 0.0505 0.7215 0.3685 0.036 Uiso calc R 1 . .
    C C16 -0.2167(2) 0.62483(11) 0.05390(16) 0.0281(4) Uani d . 1 . .
    H H16A -0.2707 0.6264 -0.0222 0.042 Uiso calc R 1 . .
    H H16B -0.1184 0.6588 0.0597 0.042 Uiso calc R 1 . .
    H H16C -0.3006 0.6398 0.1069 0.042 Uiso calc R 1 . .
    C C17 0.4115(2) 0.62589(11) 0.76362(15) 0.0278(4) Uani d . 1 . .
    H H17A 0.5186 0.6506 0.7929 0.033 Uiso calc R 1 . .
    H H17B 0.3567 0.6033 0.8275 0.033 Uiso calc R 1 . .
    C C18 0.2921(2) 0.68255(11) 0.70951(16) 0.0310(5) Uani d . 1 . .
    H H18A 0.2608 0.7187 0.7655 0.046 Uiso calc R 1 . .
    H H18B 0.1881 0.6579 0.6775 0.046 Uiso calc R 1 . .
    H H18C 0.3496 0.7079 0.6502 0.046 Uiso calc R 1 . .
    H H1O 0.594(3) 0.2375(13) 0.6331(12) 0.054(7) Uiso d D 1 . .
    H H5O 0.518(2) 0.5858(13) 0.6389(15) 0.052(7) Uiso d D 1 . .
    H H1N 0.410(3) 0.4596(8) 0.6371(14) 0.036(6) Uiso d D 1 . .
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 C1 . 1.360(2) ?
    O1 H1O . 0.859(9) ?
    O2 C7 . 1.244(2) ?
    O3 C10 . 1.366(2) ?
    O3 C15 . 1.429(2) ?
    O4 C12 . 1.369(2) ?
    O4 C16 . 1.428(2) ?
    O5 C17 . 1.428(2) ?
    O5 H5O . 0.848(10) ?
    N1 C7 . 1.345(2) ?
    N1 N2 . 1.3941(19) ?
    N1 H1N . 0.855(9) ?
    N2 C8 . 1.290(2) ?
    C1 C2 . 1.392(2) ?
    C1 C6 . 1.405(2) ?
    C2 C3 . 1.375(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.389(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.380(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.402(2) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.485(2) ?
    C8 C9 . 1.452(2) ?
    C8 H8 . 0.9500 ?
    C9 C14 . 1.398(2) ?
    C9 C10 . 1.405(2) ?
    C10 C11 . 1.391(2) ?
    C11 C12 . 1.385(2) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.395(2) ?
    C13 C14 . 1.374(2) ?
    C13 H13 . 0.9500 ?
    C14 H14 . 0.9500 ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 C18 . 1.501(3) ?
    C17 H17A . 0.9900 ?
    C17 H17B . 0.9900 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
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
    C1 O1 H1O . . 106.2(16) ?
    C10 O3 C15 . . 117.86(13) ?
    C12 O4 C16 . . 117.97(14) ?
    C17 O5 H5O . . 110.7(17) ?
    C7 N1 N2 . . 119.00(15) ?
    C7 N1 H1N . . 123.9(14) ?
    N2 N1 H1N . . 117.1(14) ?
    C8 N2 N1 . . 113.99(14) ?
    O1 C1 C2 . . 117.39(16) ?
    O1 C1 C6 . . 122.35(15) ?
    C2 C1 C6 . . 120.27(16) ?
    C3 C2 C1 . . 119.77(17) ?
    C3 C2 H2 . . 120.1 ?
    C1 C2 H2 . . 120.1 ?
    C2 C3 C4 . . 121.28(16) ?
    C2 C3 H3 . . 119.4 ?
    C4 C3 H3 . . 119.4 ?
    C5 C4 C3 . . 118.97(17) ?
    C5 C4 H4 . . 120.5 ?
    C3 C4 H4 . . 120.5 ?
    C4 C5 C6 . . 121.40(17) ?
    C4 C5 H5 . . 119.3 ?
    C6 C5 H5 . . 119.3 ?
    C5 C6 C1 . . 118.29(15) ?
    C5 C6 C7 . . 123.38(16) ?
    C1 C6 C7 . . 118.32(15) ?
    O2 C7 N1 . . 121.10(16) ?
    O2 C7 C6 . . 121.22(15) ?
    N1 C7 C6 . . 117.66(15) ?
    N2 C8 C9 . . 120.86(16) ?
    N2 C8 H8 . . 119.6 ?
    C9 C8 H8 . . 119.6 ?
    C14 C9 C10 . . 117.70(15) ?
    C14 C9 C8 . . 123.06(16) ?
    C10 C9 C8 . . 119.23(16) ?
    O3 C10 C11 . . 123.27(16) ?
    O3 C10 C9 . . 115.32(15) ?
    C11 C10 C9 . . 121.39(16) ?
    C12 C11 C10 . . 118.89(16) ?
    C12 C11 H11 . . 120.6 ?
    C10 C11 H11 . . 120.6 ?
    O4 C12 C11 . . 123.77(16) ?
    O4 C12 C13 . . 115.29(16) ?
    C11 C12 C13 . . 120.94(16) ?
    C14 C13 C12 . . 119.31(17) ?
    C14 C13 H13 . . 120.3 ?
    C12 C13 H13 . . 120.3 ?
    C13 C14 C9 . . 121.74(17) ?
    C13 C14 H14 . . 119.1 ?
    C9 C14 H14 . . 119.1 ?
    O3 C15 H15A . . 109.5 ?
    O3 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    O3 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    O4 C16 H16A . . 109.5 ?
    O4 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    O4 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O5 C17 C18 . . 111.97(15) ?
    O5 C17 H17A . . 109.2 ?
    C18 C17 H17A . . 109.2 ?
    O5 C17 H17B . . 109.2 ?
    C18 C17 H17B . . 109.2 ?
    H17A C17 H17B . . 107.9 ?
    C17 C18 H18A . . 109.5 ?
    C17 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C17 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
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
    C7 N1 N2 C8 . . . . 171.60(15) ?
    O1 C1 C2 C3 . . . . 179.24(15) ?
    C6 C1 C2 C3 . . . . -0.6(2) ?
    C1 C2 C3 C4 . . . . -0.8(2) ?
    C2 C3 C4 C5 . . . . 1.0(2) ?
    C3 C4 C5 C6 . . . . 0.2(2) ?
    C4 C5 C6 C1 . . . . -1.6(2) ?
    C4 C5 C6 C7 . . . . 178.61(15) ?
    O1 C1 C6 C5 . . . . -178.08(14) ?
    C2 C1 C6 C5 . . . . 1.7(2) ?
    O1 C1 C6 C7 . . . . 1.8(2) ?
    C2 C1 C6 C7 . . . . -178.44(14) ?
    N2 N1 C7 O2 . . . . -1.3(2) ?
    N2 N1 C7 C6 . . . . -179.38(13) ?
    C5 C6 C7 O2 . . . . 175.88(16) ?
    C1 C6 C7 O2 . . . . -4.0(2) ?
    C5 C6 C7 N1 . . . . -6.1(2) ?
    C1 C6 C7 N1 . . . . 174.10(15) ?
    N1 N2 C8 C9 . . . . -179.75(14) ?
    N2 C8 C9 C14 . . . . 12.2(2) ?
    N2 C8 C9 C10 . . . . -168.70(15) ?
    C15 O3 C10 C11 . . . . 5.3(2) ?
    C15 O3 C10 C9 . . . . -176.25(14) ?
    C14 C9 C10 O3 . . . . -178.97(14) ?
    C8 C9 C10 O3 . . . . 1.9(2) ?
    C14 C9 C10 C11 . . . . -0.5(2) ?
    C8 C9 C10 C11 . . . . -179.61(15) ?
    O3 C10 C11 C12 . . . . 177.63(14) ?
    C9 C10 C11 C12 . . . . -0.7(2) ?
    C16 O4 C12 C11 . . . . 6.8(2) ?
    C16 O4 C12 C13 . . . . -173.16(15) ?
    C10 C11 C12 O4 . . . . -178.49(15) ?
    C10 C11 C12 C13 . . . . 1.5(2) ?
    O4 C12 C13 C14 . . . . 179.01(14) ?
    C11 C12 C13 C14 . . . . -0.9(3) ?
    C12 C13 C14 C9 . . . . -0.3(3) ?
    C10 C9 C14 C13 . . . . 1.0(2) ?
    C8 C9 C14 C13 . . . . -179.89(15) ?
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
    O1 H1o O2 . 0.860(10)
                        1.74(2) 2.528(2) 151(2) y
    O5 H5o N2 3_666 0.850(10)
                            2.070(10)
                                    2.847(2) 152(2) y
    N1 H1n O5 . 0.860(10)
                        2.090(10)
                                2.894(2) 157(2) y
