##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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  #
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data_global
_audit_creation_method     'Jana2006 Version : 22/06/2010'
_journal_date_recd_electronic     2010-07-02
_journal_date_accepted     2010-07-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      8
_journal_page_first     o2062
_journal_page_last     o2062
_journal_paper_category     QO
_journal_coeditor_code     FK2021
_publ_contact_author_name     'Karla Fejfarov\'a'
_publ_contact_author_address
;
Institute of Physics
Na Slovance 2
182 21 Praha 8
Czech Republic
;
_publ_contact_author_email     fejfarov@fzu.cz
_publ_contact_author_fax     '+420 233 343 184'
_publ_contact_author_phone     '+420 220 318 594'
_publ_section_title
;
(<i>E</i>)-4-Bromo-<i>N</i>-(2,3,4-trimethoxybenzylidene)aniline
;
loop_
    _publ_author_name
    _publ_author_address
    'Fejfarov\'a, Karla'
;
Institute of Physics
Na Slovance 2
182 21 Praha 8
Czech Republic
;
    'Khalaji, Aliakbar Dehno'
;
Department of Chemistry
Faculty of Science
Golestan University
Gorgan
Iran
;
    'Du\<sek, Michal'
;
Institute of Physics
Na Slovance 2
182 21 Praha 8
Czech Republic
;
data_I
_chemical_name_systematic
;
(<i>E</i>)-4-Bromo-<i>N</i>-(2,3,4-trimethoxybenzylidene)aniline
;
_chemical_formula_moiety     'C16 H16 Br1 N1 O3'
_chemical_formula_sum     'C16 H16 Br1 N1 O3'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C16 H16 Br1 N1 O3'
_chemical_formula_weight     350.2
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,-y,-z
_cell_length_a     7.9103(3)
_cell_length_b     9.9902(4)
_cell_length_c     10.7821(3)
_cell_angle_alpha     93.068(3)
_cell_angle_beta     108.568(3)
_cell_angle_gamma     109.679(3)
_cell_volume     748.10(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     11782
_cell_measurement_theta_min     4.3994
_cell_measurement_theta_max     66.6530
_cell_measurement_temperature     120
_cell_special_details
;
;
_exptl_crystal_description     'irregular shape'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.4852
_exptl_crystal_size_mid     0.3782
_exptl_crystal_size_min     0.2533
_exptl_crystal_density_diffrn     1.5542
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     356
_exptl_absorpt_coefficient_mu     3.832
_exptl_absorpt_correction_type     analytical
_exptl_absorpt_process_details     '(CrysAlis Pro; Oxford Diffraction, 2009)'
_exptl_absorpt_correction_T_min     0.308
_exptl_absorpt_correction_T_max     0.631
_exptl_special_details
;
CrysAlisPro (Oxford Diffraction, 2009).
Analytical numeric absorption correction using a multifaceted crystal
model.
;
_diffrn_ambient_temperature     120
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source     'X-ray tube'
_diffrn_radiation_monochromator     'mirror'
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with an Atlas
(Gemini Ultra Cu) detector
;
_diffrn_measurement_device     'four-cycle diffractometer'
_diffrn_measurement_method     'Rotation method data acquisition using \w scans'
_diffrn_detector_area_resol_mean     10.3784
_diffrn_reflns_number     11571
_diffrn_reflns_av_R_equivalents     0.0229
_diffrn_reflns_av_sigmaI/netI     0.0072
_diffrn_reflns_theta_min     4.43
_diffrn_reflns_theta_max     65.05
_diffrn_reflns_theta_full     65.05
_diffrn_measured_fraction_theta_max     0.99
_diffrn_measured_fraction_theta_full     0.99
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_reflns_reduction_process
;
Integration of the CCD images was done by program CrysAlis Pro
(Oxford diffraction, 2009). The same program was used for indexing of the
crystal shape and absorption correction.
;
_refine_special_details
;
The refinement was carried out against all reflections. The conventional
<i>R</i>-factor is always based on <i>F</i>. The goodness of fit as well as
the weighted <i>R</i>-factor are based on <i>F</i> and <i>F</i>^2^ for
refinement carried out on <i>F</i> and <i>F</i>^2^, respectively. The
threshold expression is used only for calculating <i>R</i>-factors <i>etc</i>.
and it is not relevant to the choice of reflections for refinement.
The program used for refinement, Jana2006, uses the weighting scheme based on
the experimental expectations, see _refine_ls_weighting_details, that does not
force <i>S</i> to be one. Therefore the values of <i>S</i> are usually larger
than the ones from the <i>SHELX</i> program.
;
_reflns_number_total     2546
_reflns_number_gt     2485
_reflns_threshold_expression     I>3\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_all     0.0259
_refine_ls_R_factor_gt     0.0255
_refine_ls_wR_factor_gt     0.0925
_refine_ls_wR_factor_ref     0.0931
_refine_ls_goodness_of_fit_ref     1.73
_refine_ls_restrained_S_all     ?
_refine_ls_number_reflns     2546
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_number_constraints     64
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     sigma
_refine_ls_weighting_details     'w=1/[\s^2^(I)+0.0025000002I^2^]'
_refine_ls_shift/su_max     0.0097
_refine_ls_shift/su_mean     0.0018
_refine_diff_density_max     0.29
_refine_diff_density_min     -0.28
_refine_ls_extinction_method     'none'
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
_refine_ls_abs_structure_Rogers     ?
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.018 0.009 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
    H 0.000 0.000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
    Br -0.676 1.281 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
    N 0.031 0.018 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
    O 0.049 0.032 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
_computing_data_collection     'Crysalis Pro (Oxford Diffraction, 2009)'
_computing_cell_refinement     'Crysalis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction     'Crysalis Pro (Oxford Diffraction, 2009)'
_computing_structure_solution     'SIR2002 (Burla <i>et al.</i>, 2003)'
_computing_structure_refinement
                                 'JANA2006 (Pet\<r\'i\<cek <i>et al.</i>, 2006)'
_computing_molecular_graphics     'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material
                                 'JANA2006 (Pet\<r\'i\<cek <i>et al.</i>, 2006)'
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 0.74999(3) 0.08307(2) 0.325568(16) 0.02973(14) Uani d . 1 . .
    O O1 0.27449(16) 0.17106(14) 0.96566(12) 0.0209(5) Uani d . 1 . .
    O O2 0.28261(17) 0.27191(14) 1.21239(13) 0.0204(5) Uani d . 1 . .
    O O3 0.58807(17) 0.49203(14) 1.37866(12) 0.0217(5) Uani d . 1 . .
    N N1 0.7545(2) 0.28811(17) 0.86865(15) 0.0205(6) Uani d . 1 . .
    C C1 0.5987(2) 0.27332(18) 0.88986(17) 0.0196(6) Uani d . 1 . .
    C C2 0.6019(2) 0.33388(19) 1.01757(17) 0.0183(6) Uani d . 1 . .
    C C3 0.4387(2) 0.27855(18) 1.05351(17) 0.0179(6) Uani d . 1 . .
    C C4 0.4391(2) 0.33244(18) 1.17524(16) 0.0177(6) Uani d . 1 . .
    C C5 0.6034(2) 0.44399(19) 1.26324(17) 0.0188(6) Uani d . 1 . .
    C C6 0.7671(2) 0.50042(19) 1.22894(17) 0.0205(7) Uani d . 1 . .
    C C7 0.7633(2) 0.4451(2) 1.10740(17) 0.0209(7) Uani d . 1 . .
    C C8 0.2463(3) 0.0301(2) 1.0001(2) 0.0275(7) Uani d . 1 . .
    C C9 0.1411(2) 0.3364(2) 1.16845(19) 0.0225(7) Uani d . 1 . .
    C C10 0.7574(3) 0.5963(2) 1.4782(2) 0.0283(8) Uani d . 1 . .
    C C11 0.7401(2) 0.23365(19) 0.74029(17) 0.0190(6) Uani d . 1 . .
    C C12 0.8644(2) 0.16622(19) 0.73130(18) 0.0214(7) Uani d . 1 . .
    C C13 0.8630(3) 0.1162(2) 0.60794(19) 0.0228(7) Uani d . 1 . .
    C C14 0.7397(3) 0.1383(2)   0.49439(18) 0.0212(7) Uani d . 1 . .
    C C15 0.6134(3) 0.2048(2) 0.50017(19) 0.0232(7) Uani d . 1 . .
    C C16 0.6156(3) 0.2530(2)   0.62404(18) 0.0224(7) Uani d . 1 . .
    H H1 0.477112 0.22121 0.820107 0.0236 Uiso d . 1 . .
    H H6 0.880465 0.576586 1.289179 0.0246 Uiso d . 1 . .
    H H7 0.875405 0.484421 1.084082 0.0251 Uiso d . 1 . .
    H H8a 0.117756 -0.035146 0.948638 0.0329 Uiso d . 1 . .
    H H8b 0.336604 -0.004589 0.981472 0.0329 Uiso d . 1 . .
    H H8c 0.265545 0.035921 1.093009 0.0329 Uiso d . 1 . .
    H H9a 0.039226 0.294309 1.201348 0.0269 Uiso d . 1 . .
    H H9b 0.200061 0.438601 1.201714 0.0269 Uiso d . 1 . .
    H H9c 0.089588 0.3194 1.073 0.0269 Uiso d . 1 . .
    H H10a 0.725742 0.625109 1.551587 0.034 Uiso d . 1 . .
    H H10b 0.852651 0.554334 1.508865 0.034 Uiso d . 1 . .
    H H10c 0.807226 0.679308 1.440879 0.034 Uiso d . 1 . .
    H H12 0.95208 0.154077 0.810937 0.0256 Uiso d . 1 . .
    H H13 0.946288 0.067032 0.60173 0.0274 Uiso d . 1 . .
    H H15 0.526458 0.217114 0.42029 0.0278 Uiso d . 1 . .
    H H16 0.530309 0.300348 0.629778 0.0268 Uiso d . 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
    _atom_site_aniso_type_symbol
    Br1 0.03787(19) 0.03187(19) 0.02105(19) 0.00904(13) 0.01747(12) 0.00097(11)
                                                                              Br
    O1 0.0192(6) 0.0209(7) 0.0176(6) 0.0033(5) 0.0045(5) 0.0034(5) O
    O2 0.0202(6) 0.0239(7) 0.0230(7) 0.0091(5) 0.0132(5) 0.0103(5) O
    O3 0.0227(6) 0.0259(7) 0.0175(6) 0.0079(5) 0.0099(5) 0.0019(5) O
    N1 0.0230(7) 0.0245(8) 0.0159(7) 0.0089(6) 0.0090(6) 0.0047(6) N
    C1 0.0214(8) 0.0192(8) 0.0189(9) 0.0072(7) 0.0078(7) 0.0067(7) C
    C2 0.0206(8) 0.0211(8) 0.0174(8) 0.0098(7) 0.0094(7) 0.0071(7) C
    C3 0.0179(8) 0.0183(8) 0.0178(8) 0.0071(7) 0.0059(6) 0.0058(7) C
    C4 0.0196(8) 0.0197(8) 0.0192(8) 0.0096(7) 0.0107(7) 0.0095(7) C
    C5 0.0214(8) 0.0216(9) 0.0177(8) 0.0104(7) 0.0093(7) 0.0069(7) C
    C6 0.0196(8) 0.0213(9) 0.0199(9) 0.0059(7) 0.0082(7) 0.0030(7) C
    C7 0.0201(8) 0.0238(9) 0.0213(9) 0.0073(7) 0.0114(7) 0.0060(7) C
    C8 0.0309(9) 0.0197(9) 0.0304(11) 0.0044(8) 0.0147(8) 0.0038(8) C
    C9 0.0187(9) 0.0268(9) 0.0248(10) 0.0093(8) 0.0105(7) 0.0066(7) C
    C10 0.0256(9) 0.0369(11) 0.0186(9) 0.0094(8) 0.0066(7) -0.0024(8) C
    C11 0.0192(8) 0.0185(8) 0.0188(9) 0.0039(7) 0.0091(7) 0.0044(7) C
    C12 0.0208(8) 0.0256(9) 0.0208(9) 0.0097(7) 0.0098(7) 0.0078(7) C
    C13 0.0232(9) 0.0227(9) 0.0265(10) 0.0097(7) 0.0126(7) 0.0055(7) C
    C14 0.0261(9) 0.0205(9) 0.0186(9) 0.0053(7) 0.0140(7) 0.0022(7) C
    C15 0.0277(9) 0.0249(9) 0.0185(9) 0.0105(8) 0.0088(7) 0.0083(7) C
    C16 0.0255(9) 0.0241(9) 0.0223(9) 0.0118(7) 0.0116(7) 0.0066(7) C
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Br1 C14 . . 1.908(2) no
    O1 C3 . . 1.3805(16) no
    O1 C8 . . 1.438(2) no
    O2 C4 . . 1.377(2) no
    O2 C9 . . 1.440(3) no
    O3 C5 . . 1.365(2) no
    O3 C10 . . 1.4342(19) no
    N1 C1 . . 1.286(3) no
    N1 C11 . . 1.415(3) no
    C1 C2 . . 1.463(3) no
    C1 H1 . . 0.96 no
    C2 C3 . . 1.408(3) no
    C2 C7 . . 1.3946(19) no
    C3 C4 . . 1.391(3) no
    C4 C5 . . 1.3990(19) no
    C5 C6 . . 1.403(3) no
    C6 C7 . . 1.382(3) no
    C6 H6 . . 0.96 no
    C7 H7 . . 0.96 no
    C8 H8a . . 0.96 no
    C8 H8b . . 0.96 no
    C8 H8c . . 0.96 no
    C9 H9a . . 0.96 no
    C9 H9b . . 0.96 no
    C9 H9c . . 0.96 no
    C10 H10a . . 0.96 no
    C10 H10b . . 0.96 no
    C10 H10c . . 0.96 no
    C11 C12 . . 1.390(3) no
    C11 C16 . . 1.395(3) no
    C12 C13 . . 1.391(3) no
    C12 H12 . . 0.96 no
    C13 C14 . . 1.383(3) no
    C13 H13 . . 0.96 no
    C14 C15 . . 1.387(3) no
    C15 C16 . . 1.388(3) no
    C15 H15 . . 0.96 no
    C16 H16 . . 0.96 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C3 O1 C8 . . . 113.46(13) no
    C4 O2 C9 . . . 112.97(15) no
    C5 O3 C10 . . . 117.80(15) no
    C1 N1 C11 . . . 118.43(13) no
    N1 C1 C2 . . . 121.70(13) no
    N1 C1 H1 . . . 119.1502 no
    C2 C1 H1 . . . 119.1489 no
    C1 C2 C3 . . . 119.84(13) no
    C1 C2 C7 . . . 122.20(18) no
    C3 C2 C7 . . . 117.96(17) no
    O1 C3 C2 . . . 119.60(16) no
    O1 C3 C4 . . . 119.38(16) no
    C2 C3 C4 . . . 121.01(13) no
    O2 C4 C3 . . . 120.43(12) no
    O2 C4 C5 . . . 119.83(17) no
    C3 C4 C5 . . . 119.66(17) no
    O3 C5 C4 . . . 115.31(17) no
    O3 C5 C6 . . . 124.62(13) no
    C4 C5 C6 . . . 120.06(17) no
    C5 C6 C7 . . . 119.23(13) no
    C5 C6 H6 . . . 120.3876 no
    C7 C6 H6 . . . 120.3865 no
    C2 C7 C6 . . . 122.09(18) no
    C2 C7 H7 . . . 118.9551 no
    C6 C7 H7 . . . 118.9554 no
    O1 C8 H8a . . . 109.4712 no
    O1 C8 H8b . . . 109.4712 no
    O1 C8 H8c . . . 109.4713 no
    H8a C8 H8b . . . 109.4713 no
    H8a C8 H8c . . . 109.4709 no
    H8b C8 H8c . . . 109.4714 no
    O2 C9 H9a . . . 109.4709 no
    O2 C9 H9b . . . 109.4713 no
    O2 C9 H9c . . . 109.4711 no
    H9a C9 H9b . . . 109.4714 no
    H9a C9 H9c . . . 109.4709 no
    H9b C9 H9c . . . 109.4718 no
    O3 C10 H10a . . . 109.4713 no
    O3 C10 H10b . . . 109.4716 no
    O3 C10 H10c . . . 109.4711 no
    H10a C10 H10b . . . 109.4714 no
    H10a C10 H10c . . . 109.4707 no
    H10b C10 H10c . . . 109.4713 no
    N1 C11 C12 . . . 117.91(16) no
    N1 C11 C16 . . . 122.8(2) no
    C12 C11 C16 . . . 119.21(19) no
    C11 C12 C13 . . . 120.60(17) no
    C11 C12 H12 . . . 119.6985 no
    C13 C12 H12 . . . 119.6991 no
    C12 C13 C14 . . . 118.9(2) no
    C12 C13 H13 . . . 120.5337 no
    C14 C13 H13 . . . 120.5339 no
    Br1 C14 C13 . . . 119.31(18) no
    Br1 C14 C15 . . . 118.89(14) no
    C13 C14 C15 . . . 121.8(2) no
    C14 C15 C16 . . . 118.52(18) no
    C14 C15 H15 . . . 120.7399 no
    C16 C15 H15 . . . 120.7397 no
    C11 C16 C15 . . . 120.9(2) no
    C11 C16 H16 . . . 119.5302 no
    C15 C16 H16 . . . 119.5303 no
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
    C8 O1 C3 C2 . . . . 103.6(2) no
    C8 O1 C3 C4 . . . . -77.6(2) no
    C9 O2 C4 C3 . . . . -88.7(2) no
    C9 O2 C4 C5 . . . . 94.54(19) no
    C10 O3 C5 C4 . . . . 174.08(16) no
    C10 O3 C5 C6 . . . . -7.2(3) no
    C11 N1 C1 C2 . . . . -176.48(16) no
    C1 N1 C11 C12 . . . . -140.37(18) no
    C1 N1 C11 C16 . . . . 43.7(3) no
    N1 C1 C2 C3 . . . . -159.30(17) no
    N1 C1 C2 C7 . . . . 20.0(3) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    ? ? ? ? ? ? ? ? ? ? ?