##############################################################################
###                                                                        ###
###        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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N'-(2-Bromobenzylidene)-3,4,5-trimethoxybenzohydrazide methanol solvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H17 Br N2 O4, C H4 O'
_chemical_formula_sum     'C18 H21 Br N2 O5'
_chemical_formula_iupac     'C17 H17 Br N2 O4, C H4 O'
_chemical_formula_weight     425.28
_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     12.9234(7)
_cell_length_b     4.9159(3)
_cell_length_c     29.3975(17)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1867.63(19)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4139
_cell_measurement_theta_min     2.77
_cell_measurement_theta_max     26.81
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.33
_exptl_crystal_density_diffrn     1.512
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     872
_exptl_absorpt_coefficient_mu     2.232
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.4553
_exptl_absorpt_correction_T_max     0.4788
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(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 1000 CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8158
_diffrn_reflns_av_R_equivalents     0.0274
_diffrn_reflns_av_sigmaI/netI     0.0612
_diffrn_reflns_theta_min     1.39
_diffrn_reflns_theta_max     27.01
_diffrn_reflns_theta_full     27.01
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -2
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -34
_diffrn_reflns_limit_l_max     37
_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     3799
_reflns_number_gt     3206
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0410
_refine_ls_R_factor_gt     0.0295
_refine_ls_wR_factor_gt     0.0664
_refine_ls_wR_factor_ref     0.0801
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     3799
_refine_ls_number_parameters     240
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'calc w=1/[σ²(Fo²)+0.8008P] 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     0.331
_refine_diff_density_min     -0.261
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1720 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.008(8)
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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2003)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2003)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (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
    Br Br1 0.61656(2) 1.31840(7) 0.659414(16) 0.03707(11) Uani d . 1 . .
    C C1 0.5590(2) 0.7908(6) 0.89278(10) 0.0193(6) Uani d . 1 . .
    C C2 0.6409(2) 0.9755(6) 0.89566(11) 0.0195(6) Uani d . 1 . .
    H H2 0.6593 1.0831 0.8701 0.023 Uiso calc R 1 . .
    C C3 0.6953(2) 1.0008(6) 0.93627(11) 0.0207(7) Uani d . 1 . .
    C C4 0.6698(2) 0.8389(6) 0.97327(10) 0.0186(6) Uani d . 1 . .
    C C5 0.5855(2) 0.6608(6) 0.97056(11) 0.0215(7) Uani d . 1 . .
    C C6 0.5308(2) 0.6357(6) 0.93023(11) 0.0211(7) Uani d . 1 . .
    H H6 0.4742 0.5129 0.9282 0.025 Uiso calc R 1 . .
    C C7 0.4968(2) 0.7557(6) 0.85047(11) 0.0212(7) Uani d . 1 . .
    C C8 0.5282(3) 0.9221(7) 0.73624(12) 0.0276(7) Uani d . 1 . .
    H H8 0.5962 0.9952 0.7377 0.033 Uiso calc R 1 . .
    C C9 0.4707(3) 0.9235(7) 0.69320(11) 0.0254(7) Uani d . 1 . .
    C C10 0.4991(2) 1.0835(6) 0.65573(14) 0.0264(7) Uani d . 1 . .
    C C11 0.4448(3) 1.0814(8) 0.61551(12) 0.0337(8) Uani d . 1 . .
    H H11 0.4657 1.1955 0.5911 0.040 Uiso calc R 1 . .
    C C12 0.3603(3) 0.9139(8) 0.61066(13) 0.0362(9) Uani d . 1 . .
    H H12 0.3235 0.9084 0.5827 0.043 Uiso calc R 1 . .
    C C13 0.3292(3) 0.7520(8) 0.64720(12) 0.0344(9) Uani d . 1 . .
    H H13 0.2709 0.6357 0.6441 0.041 Uiso calc R 1 . .
    C C14 0.3830(3) 0.7604(8) 0.68790(14) 0.0312(8) Uani d . 1 . .
    H H14 0.3598 0.6530 0.7127 0.037 Uiso calc R 1 . .
    C C15 0.8028(3) 1.3547(7) 0.90665(12) 0.0254(7) Uani d . 1 . .
    H H15A 0.8276 1.2478 0.8807 0.038 Uiso calc R 1 . .
    H H15B 0.8577 1.4779 0.9168 0.038 Uiso calc R 1 . .
    H H15C 0.7422 1.4611 0.8975 0.038 Uiso calc R 1 . .
    C C16 0.7819(3) 0.6441(7) 1.02794(14) 0.0378(9) Uani d . 1 . .
    H H16A 0.7402 0.4792 1.0242 0.057 Uiso calc R 1 . .
    H H16B 0.8003 0.6660 1.0601 0.057 Uiso calc R 1 . .
    H H16C 0.8451 0.6289 1.0097 0.057 Uiso calc R 1 . .
    C C17 0.4812(3) 0.3298(7) 1.00811(13) 0.0294(8) Uani d . 1 . .
    H H17A 0.4160 0.4211 1.0006 0.044 Uiso calc R 1 . .
    H H17B 0.4748 0.2407 1.0378 0.044 Uiso calc R 1 . .
    H H17C 0.4968 0.1932 0.9848 0.044 Uiso calc R 1 . .
    C C18 0.2740(4) 0.2319(9) 0.78016(15) 0.0461(11) Uani d . 1 . .
    H H18A 0.3183 0.2281 0.7531 0.069 Uiso calc R 1 . .
    H H18B 0.2092 0.1360 0.7737 0.069 Uiso calc R 1 . .
    H H18C 0.3096 0.1426 0.8055 0.069 Uiso calc R 1 . .
    N N2 0.4860(2) 0.8218(6) 0.77170(9) 0.0247(6) Uani d . 1 . .
    N N1 0.5432(2) 0.8335(6) 0.81116(9) 0.0254(6) Uani d . 1 . .
    H H1A 0.6079 0.8897 0.8109 0.030 Uiso calc R 1 . .
    O O1 0.77516(17) 1.1759(4) 0.94291(7) 0.0240(5) Uani d . 1 . .
    O O2 0.72395(17) 0.8738(5) 1.01327(8) 0.0247(5) Uani d . 1 . .
    O O3 0.56273(16) 0.5255(5) 1.00977(8) 0.0279(5) Uani d . 1 . .
    O O4 0.40936(17) 0.6632(5) 0.85149(8) 0.0282(5) Uani d . 1 . .
    O O5 0.25214(18) 0.5045(5) 0.79189(9) 0.0319(6) Uani d . 1 . .
    H H5 0.2973 0.5615 0.8101 0.048 Uiso calc R 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
    Br1 C10 . 1.911(3) ?
    C1 C6 . 1.388(4) ?
    C1 C2 . 1.397(4) ?
    C1 C7 . 1.491(4) ?
    C2 C3 . 1.391(4) ?
    C2 H2 . 0.9500 ?
    C3 O1 . 1.358(4) ?
    C3 C4 . 1.388(4) ?
    C4 O2 . 1.379(4) ?
    C4 C5 . 1.400(5) ?
    C5 O3 . 1.363(4) ?
    C5 C6 . 1.386(4) ?
    C6 H6 . 0.9500 ?
    C7 O4 . 1.218(4) ?
    C7 N1 . 1.357(4) ?
    C8 N2 . 1.276(4) ?
    C8 C9 . 1.467(4) ?
    C8 H8 . 0.9500 ?
    C9 C14 . 1.398(5) ?
    C9 C10 . 1.402(5) ?
    C10 C11 . 1.375(5) ?
    C11 C12 . 1.375(6) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.396(5) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.384(5) ?
    C13 H13 . 0.9500 ?
    C14 H14 . 0.9500 ?
    C15 O1 . 1.427(4) ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    C16 O2 . 1.422(4) ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 O3 . 1.428(4) ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 O5 . 1.412(5) ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    N2 N1 . 1.377(4) ?
    N1 H1A . 0.8800 ?
    O5 H5 . 0.8400 ?
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
    C6 C1 C2 . . 120.5(3) ?
    C6 C1 C7 . . 117.1(3) ?
    C2 C1 C7 . . 122.3(3) ?
    C3 C2 C1 . . 119.5(3) ?
    C3 C2 H2 . . 120.2 ?
    C1 C2 H2 . . 120.2 ?
    O1 C3 C4 . . 115.6(3) ?
    O1 C3 C2 . . 124.3(3) ?
    C4 C3 C2 . . 120.1(3) ?
    O2 C4 C3 . . 118.5(3) ?
    O2 C4 C5 . . 121.4(3) ?
    C3 C4 C5 . . 119.9(3) ?
    O3 C5 C6 . . 124.7(3) ?
    O3 C5 C4 . . 115.2(3) ?
    C6 C5 C4 . . 120.1(3) ?
    C5 C6 C1 . . 119.7(3) ?
    C5 C6 H6 . . 120.2 ?
    C1 C6 H6 . . 120.2 ?
    O4 C7 N1 . . 122.4(3) ?
    O4 C7 C1 . . 121.5(3) ?
    N1 C7 C1 . . 116.1(3) ?
    N2 C8 C9 . . 119.3(3) ?
    N2 C8 H8 . . 120.3 ?
    C9 C8 H8 . . 120.3 ?
    C14 C9 C10 . . 116.5(3) ?
    C14 C9 C8 . . 120.3(3) ?
    C10 C9 C8 . . 123.2(3) ?
    C11 C10 C9 . . 122.6(3) ?
    C11 C10 Br1 . . 117.3(3) ?
    C9 C10 Br1 . . 120.1(3) ?
    C12 C11 C10 . . 119.9(3) ?
    C12 C11 H11 . . 120.0 ?
    C10 C11 H11 . . 120.0 ?
    C11 C12 C13 . . 119.4(3) ?
    C11 C12 H12 . . 120.3 ?
    C13 C12 H12 . . 120.3 ?
    C14 C13 C12 . . 120.2(4) ?
    C14 C13 H13 . . 119.9 ?
    C12 C13 H13 . . 119.9 ?
    C13 C14 C9 . . 121.4(4) ?
    C13 C14 H14 . . 119.3 ?
    C9 C14 H14 . . 119.3 ?
    O1 C15 H15A . . 109.5 ?
    O1 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    O1 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    O2 C16 H16A . . 109.5 ?
    O2 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    O2 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O3 C17 H17A . . 109.5 ?
    O3 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    O3 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    O5 C18 H18A . . 109.5 ?
    O5 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    O5 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C8 N2 N1 . . 116.2(3) ?
    C7 N1 N2 . . 117.9(3) ?
    C7 N1 H1A . . 121.1 ?
    N2 N1 H1A . . 121.1 ?
    C3 O1 C15 . . 118.2(2) ?
    C4 O2 C16 . . 115.3(2) ?
    C5 O3 C17 . . 117.4(3) ?
    C18 O5 H5 . . 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
    C6 C1 C2 C3 . . . . 0.9(4) ?
    C7 C1 C2 C3 . . . . 179.4(3) ?
    C1 C2 C3 O1 . . . . -179.2(3) ?
    C1 C2 C3 C4 . . . . 1.5(4) ?
    O1 C3 C4 O2 . . . . 2.0(4) ?
    C2 C3 C4 O2 . . . . -178.6(3) ?
    O1 C3 C4 C5 . . . . 177.0(3) ?
    C2 C3 C4 C5 . . . . -3.6(4) ?
    O2 C4 C5 O3 . . . . -0.7(4) ?
    C3 C4 C5 O3 . . . . -175.6(3) ?
    O2 C4 C5 C6 . . . . 178.2(3) ?
    C3 C4 C5 C6 . . . . 3.3(4) ?
    O3 C5 C6 C1 . . . . 177.8(3) ?
    C4 C5 C6 C1 . . . . -1.0(5) ?
    C2 C1 C6 C5 . . . . -1.2(5) ?
    C7 C1 C6 C5 . . . . -179.7(3) ?
    C6 C1 C7 O4 . . . . 21.3(4) ?
    C2 C1 C7 O4 . . . . -157.2(3) ?
    C6 C1 C7 N1 . . . . -159.0(3) ?
    C2 C1 C7 N1 . . . . 22.5(4) ?
    N2 C8 C9 C14 . . . . -15.7(5) ?
    N2 C8 C9 C10 . . . . 164.3(3) ?
    C14 C9 C10 C11 . . . . -0.5(5) ?
    C8 C9 C10 C11 . . . . 179.6(3) ?
    C14 C9 C10 Br1 . . . . 179.1(2) ?
    C8 C9 C10 Br1 . . . . -0.9(4) ?
    C9 C10 C11 C12 . . . . -1.2(5) ?
    Br1 C10 C11 C12 . . . . 179.2(3) ?
    C10 C11 C12 C13 . . . . 1.5(5) ?
    C11 C12 C13 C14 . . . . 0.0(6) ?
    C12 C13 C14 C9 . . . . -1.8(6) ?
    C10 C9 C14 C13 . . . . 1.9(5) ?
    C8 C9 C14 C13 . . . . -178.1(3) ?
    C9 C8 N2 N1 . . . . -178.4(3) ?
    O4 C7 N1 N2 . . . . 4.1(5) ?
    C1 C7 N1 N2 . . . . -175.7(3) ?
    C8 N2 N1 C7 . . . . 173.1(3) ?
    C4 C3 O1 C15 . . . . -177.9(3) ?
    C2 C3 O1 C15 . . . . 2.7(4) ?
    C3 C4 O2 C16 . . . . -117.3(3) ?
    C5 C4 O2 C16 . . . . 67.8(4) ?
    C6 C5 O3 C17 . . . . 4.7(5) ?
    C4 C5 O3 C17 . . . . -176.5(3) ?
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
    N1 H1A O5 3_565 0.88 2.01 2.871(4) 164.2
    O5 H5 O4 . 0.84 1.96 2.794(3) 174.8
data_global
_journal_date_recd_electronic     2008-07-08
_journal_date_accepted     2008-07-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1630
_journal_page_last     o1630
_journal_paper_category     QO
_journal_coeditor_code     WN2271
_publ_contact_author_name     'Dao-Hang He'
_publ_contact_author_address
;
School of Chemistry and Chemical Engineering,
South China University of Technology,
Guangzhou 510640, People's Republic of China
;
_publ_contact_author_email     'daohanghe@yahoo.com.cn'
_publ_contact_author_fax     '+86-20-87110234'
_publ_contact_author_phone     '+86-20-87110234'
_publ_section_title
;
N'-(2-Bromobenzylidene)-3,4,5-trimethoxybenzohydrazide methanol solvate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Zhu, Yong-Chuang' .
;
School of Chemistry and Chemical Engineering,
South China University of Technology,
Guangzhou 510640, People's Republic of China
;
    'He, Dao-Hang' .
;
School of Chemistry and Chemical Engineering,
South China University of Technology,
Guangzhou 510640, People's Republic of China
;
