##############################################################################
###                                                                        ###
###        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.                                        #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2008-11-24
_journal_date_accepted     2008-11-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      1
_journal_page_first     o29
_journal_page_last     o29
_journal_paper_category     QO
_journal_coeditor_code     SJ2559
_publ_contact_author_name     'Chun-Lin Du'
_publ_contact_author_address
;
College of Chemical Engineering & Material Science
Liaodong University
Dandong 118003
People's Republic of China
;
_publ_contact_author_email     chunlin_du@163.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
N'-(2-Hydroxy-3-methoxybenzylidene)-1,3-benzodioxole-5-carbohydrazide
monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Chun-Lin Du'
;
College of Chemical Engineering & Materials Science
Liaodong University
Dandong 118003
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N'-(2-Hydroxy-3-methoxybenzylidene)-1,3-benzodioxole-5-carbohydrazide
monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H14 N2 O5, H2 O'
_chemical_formula_sum     'C16 H16 N2 O6'
_chemical_formula_iupac     'C16 H14 N2 O5, H2 O'
_chemical_formula_weight     332.31
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     4.792(2)
_cell_length_b     12.916(3)
_cell_length_c     24.002(6)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1485.6(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3222
_cell_measurement_theta_min     2.4
_cell_measurement_theta_max     25.6
_cell_measurement_temperature     298(2)
_exptl_crystal_description     'cut from needle'
_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     1.486
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     696
_exptl_absorpt_coefficient_mu     0.115
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9740
_exptl_absorpt_correction_T_max     0.9773
_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 1K CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8595
_diffrn_reflns_av_R_equivalents     0.0301
_diffrn_reflns_av_sigmaI/netI     0.0220
_diffrn_reflns_theta_min     1.70
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     28
_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     1907
_reflns_number_gt     1639
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0395
_refine_ls_R_factor_gt     0.0315
_refine_ls_wR_factor_gt     0.0716
_refine_ls_wR_factor_ref     0.0763
_refine_ls_goodness_of_fit_ref     1.054
_refine_ls_restrained_S_all     1.053
_refine_ls_number_reflns     1907
_refine_ls_number_parameters     228
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0385P)²+0.1335P] 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     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.128
_refine_diff_density_min     -0.130
_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
    O O1 0.9802(3) 0.80320(10) 0.83305(6) 0.0447(4) Uani d . 1 . .
    H H1 0.8775 0.8121 0.8061 0.067 Uiso calc R 1 . .
    O O2 0.3794(4) 0.78499(11) 0.69933(6) 0.0563(5) Uani d . 1 . .
    O O3 1.3470(3) 0.79317(11) 0.91162(6) 0.0489(4) Uani d . 1 . .
    O O4 -0.3191(4) 0.81446(12) 0.53841(6) 0.0599(5) Uani d . 1 . .
    O O5 -0.3991(3) 0.98897(11) 0.52200(6) 0.0490(4) Uani d . 1 . .
    O O6 0.4857(4) 0.67908(12) 0.79533(6) 0.0528(4) Uani d D 1 . .
    N N1 0.7019(4) 0.92306(13) 0.75678(6) 0.0368(4) Uani d . 1 . .
    N N2 0.5153(4) 0.95059(13) 0.71517(7) 0.0374(4) Uani d D 1 . .
    C C1 1.0510(4) 0.98797(15) 0.82015(7) 0.0349(4) Uani d . 1 . .
    C C2 1.1069(4) 0.89400(14) 0.84647(8) 0.0330(4) Uani d . 1 . .
    C C3 1.3082(4) 0.88967(15) 0.88912(8) 0.0360(4) Uani d . 1 . .
    C C4 1.4481(5) 0.97831(16) 0.90522(8) 0.0415(5) Uani d . 1 . .
    H H4 1.5789 0.9754 0.9338 0.050 Uiso calc R 1 . .
    C C5 1.3937(5) 1.07197(16) 0.87871(8) 0.0449(5) Uani d . 1 . .
    H H5 1.4897 1.1314 0.8893 0.054 Uiso calc R 1 . .
    C C6 1.1978(5) 1.07680(15) 0.83680(8) 0.0418(5) Uani d . 1 . .
    H H6 1.1624 1.1397 0.8193 0.050 Uiso calc R 1 . .
    C C7 0.8453(5) 0.99888(16) 0.77596(8) 0.0388(5) Uani d . 1 . .
    H H7 0.8163 1.0643 0.7608 0.047 Uiso calc R 1 . .
    C C8 0.3608(5) 0.87806(15) 0.68878(7) 0.0371(5) Uani d . 1 . .
    C C9 0.1638(5) 0.91647(14) 0.64528(7) 0.0330(4) Uani d . 1 . .
    C C10 0.0244(5) 0.84061(15) 0.61392(8) 0.0383(5) Uani d . 1 . .
    H H10 0.0559 0.7705 0.6200 0.046 Uiso calc R 1 . .
    C C11 -0.1597(5) 0.87353(15) 0.57404(8) 0.0385(5) Uani d . 1 . .
    C C12 -0.2088(5) 0.97742(15) 0.56457(7) 0.0359(4) Uani d . 1 . .
    C C13 -0.0799(5) 1.05292(15) 0.59480(8) 0.0412(5) Uani d . 1 . .
    H H13 -0.1162 1.1227 0.5885 0.049 Uiso calc R 1 . .
    C C14 0.1088(5) 1.02087(15) 0.63555(8) 0.0386(5) Uani d . 1 . .
    H H14 0.2004 1.0705 0.6568 0.046 Uiso calc R 1 . .
    C C15 -0.4686(6) 0.88603(18) 0.50433(8) 0.0497(6) Uani d . 1 . .
    H H15A -0.6678 0.8746 0.5080 0.060 Uiso calc R 1 . .
    H H15B -0.4179 0.8765 0.4655 0.060 Uiso calc R 1 . .
    C C16 1.5697(5) 0.78022(19) 0.95022(9) 0.0522(6) Uani d . 1 . .
    H H16A 1.5365 0.8226 0.9824 0.078 Uiso calc R 1 . .
    H H16B 1.7421 0.8005 0.9330 0.078 Uiso calc R 1 . .
    H H16C 1.5806 0.7089 0.9613 0.078 Uiso calc R 1 . .
    H H2 0.499(7) 1.0186(9) 0.7078(10) 0.080 Uiso d D 1 . .
    H H6A 0.474(6) 0.7133(18) 0.7649(6) 0.080 Uiso d D 1 . .
    H H6B 0.366(5) 0.706(2) 0.8170(8) 0.080 Uiso d D 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 C2 . 1.359(2) ?
    O1 H1 . 0.8200 ?
    O2 C8 . 1.232(2) ?
    O3 C3 . 1.371(2) ?
    O3 C16 . 1.423(2) ?
    O4 C11 . 1.377(2) ?
    O4 C15 . 1.427(3) ?
    O5 C12 . 1.378(2) ?
    O5 C15 . 1.435(3) ?
    O6 H6A . 0.857(10) ?
    O6 H6B . 0.848(10) ?
    N1 C7 . 1.282(3) ?
    N1 N2 . 1.387(2) ?
    N2 C8 . 1.352(3) ?
    N2 H2 . 0.899(10) ?
    C1 C2 . 1.394(3) ?
    C1 C6 . 1.404(3) ?
    C1 C7 . 1.455(3) ?
    C2 C3 . 1.408(3) ?
    C3 C4 . 1.382(3) ?
    C4 C5 . 1.392(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.377(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.492(3) ?
    C9 C14 . 1.394(3) ?
    C9 C10 . 1.405(3) ?
    C10 C11 . 1.369(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.381(3) ?
    C12 C13 . 1.363(3) ?
    C13 C14 . 1.395(3) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
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
    C2 O1 H1 . . 109.5 ?
    C3 O3 C16 . . 117.72(17) ?
    C11 O4 C15 . . 105.99(16) ?
    C12 O5 C15 . . 105.81(15) ?
    H6A O6 H6B . . 105.5(19) ?
    C7 N1 N2 . . 114.10(16) ?
    C8 N2 N1 . . 120.86(16) ?
    C8 N2 H2 . . 122.6(19) ?
    N1 N2 H2 . . 116.6(19) ?
    C2 C1 C6 . . 119.08(18) ?
    C2 C1 C7 . . 123.01(19) ?
    C6 C1 C7 . . 117.90(18) ?
    O1 C2 C1 . . 123.91(17) ?
    O1 C2 C3 . . 116.37(16) ?
    C1 C2 C3 . . 119.72(17) ?
    O3 C3 C4 . . 125.24(18) ?
    O3 C3 C2 . . 114.56(17) ?
    C4 C3 C2 . . 120.20(18) ?
    C3 C4 C5 . . 120.09(19) ?
    C3 C4 H4 . . 120.0 ?
    C5 C4 H4 . . 120.0 ?
    C6 C5 C4 . . 120.1(2) ?
    C6 C5 H5 . . 120.0 ?
    C4 C5 H5 . . 120.0 ?
    C5 C6 C1 . . 120.83(19) ?
    C5 C6 H6 . . 119.6 ?
    C1 C6 H6 . . 119.6 ?
    N1 C7 C1 . . 123.44(18) ?
    N1 C7 H7 . . 118.3 ?
    C1 C7 H7 . . 118.3 ?
    O2 C8 N2 . . 122.73(19) ?
    O2 C8 C9 . . 120.92(19) ?
    N2 C8 C9 . . 116.35(16) ?
    C14 C9 C10 . . 119.66(18) ?
    C14 C9 C8 . . 123.96(18) ?
    C10 C9 C8 . . 116.36(17) ?
    C11 C10 C9 . . 117.68(18) ?
    C11 C10 H10 . . 121.2 ?
    C9 C10 H10 . . 121.2 ?
    C10 C11 O4 . . 128.26(18) ?
    C10 C11 C12 . . 121.75(19) ?
    O4 C11 C12 . . 109.99(18) ?
    C13 C12 O5 . . 128.10(17) ?
    C13 C12 C11 . . 122.03(18) ?
    O5 C12 C11 . . 109.86(17) ?
    C12 C13 C14 . . 117.03(17) ?
    C12 C13 H13 . . 121.5 ?
    C14 C13 H13 . . 121.5 ?
    C9 C14 C13 . . 121.83(18) ?
    C9 C14 H14 . . 119.1 ?
    C13 C14 H14 . . 119.1 ?
    O4 C15 O5 . . 108.32(17) ?
    O4 C15 H15A . . 110.0 ?
    O5 C15 H15A . . 110.0 ?
    O4 C15 H15B . . 110.0 ?
    O5 C15 H15B . . 110.0 ?
    H15A C15 H15B . . 108.4 ?
    O3 C16 H16A . . 109.5 ?
    O3 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    O3 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
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
    O1 H1 N1 . 0.82 2.04 2.743(2) 143.4
    O1 H1 O6 . 0.82 2.56 3.001(2) 115.2
    N2 H2 O6 3_656 0.899(10) 2.075(11) 2.962(2) 168(3)
    O6 H6A O2 . 0.857(10) 1.880(12) 2.728(2) 170(3)
    O6 H6B O1 1_455 0.848(10) 2.269(16) 3.043(2) 152(2)
    O6 H6B O3 1_455 0.848(10) 2.538(19) 3.226(2) 139(2)
