##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-08-12
_journal_date_accepted     2005-08-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue     10
_journal_page_first     o3222
_journal_page_last     o3223
_journal_paper_category     EO
_journal_coeditor_code     OB6571
_publ_contact_author_name     'Dr Chun-Bao Li'
_publ_contact_author_address
;
Department of Chemistry
Tianjin University
Tianjin 300072
People's Republic of China
;
_publ_contact_author_email     walsoniazhang@hotmail.com
_publ_contact_author_fax     '86 022 27403475'
_publ_contact_author_phone     '86 022 27404933'
_publ_section_title
;
2,3,4-Trimethoxy-6-methylbenzaldehyde
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Wu-Jun Zhang' .
;
Department of Chemistry
Tianjin University
Tianjin 300072
People's Republic of China
;
    'Ming Lu' .
;
Department of Chemistry
Tianjin University
Tianjin 300072
People's Republic of China
;
    'Da-Chang Li' .
;
Department of Chemistry
Tianjin University
Tianjin 300072
People's Republic of China
;
    'Chun-Bao Li' .
;
Department of Chemistry
Tianjin University
Tianjin 300072
People's Republic of China
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
2,3,4-trimethoxy-6-methylbenzaldehyde
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H14 O4'
_chemical_formula_sum     'C11 H14 O4'
_chemical_formula_iupac     'C11 H14 O4'
_chemical_formula_weight     210.22
_chemical_melting_point     333
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
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     9.239(2)
_cell_length_b     7.3884(15)
_cell_length_c     15.649(3)
_cell_angle_alpha     90.00
_cell_angle_beta     92.329(3)
_cell_angle_gamma     90.00
_cell_volume     1067.3(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1636
_cell_measurement_theta_min     2.61
_cell_measurement_theta_max     26.26
_cell_measurement_temperature     294(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.308
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     448
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.972
_exptl_absorpt_correction_T_max     0.988
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     294(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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5806
_diffrn_reflns_av_R_equivalents     0.0352
_diffrn_reflns_av_sigmaI/netI     0.0440
_diffrn_reflns_theta_min     2.52
_diffrn_reflns_theta_max     26.39
_diffrn_reflns_theta_full     26.39
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     4
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     .
_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 > 2sigma(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     2180
_reflns_number_gt     1368
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0746
_refine_ls_R_factor_gt     0.0406
_refine_ls_wR_factor_gt     0.1024
_refine_ls_wR_factor_ref     0.1193
_refine_ls_goodness_of_fit_ref     1.026
_refine_ls_restrained_S_all     1.026
_refine_ls_number_reflns     2180
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0548P)²+0.1632P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.180
_refine_diff_density_min     -0.141
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.019(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    '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, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
loop_
    _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
    _atom_site_type_symbol
    O1 0.9270(2) 1.0152(2) 0.77398(10) 0.0831(6) Uani d . 1 . . O
    O2 0.76757(13) 1.30037(15) 0.96232(8) 0.0464(4) Uani d . 1 . . O
    O3 0.68164(13) 1.16631(16) 1.11355(8) 0.0450(4) Uani d . 1 . . O
    O4 0.71589(14) 0.80823(16) 1.14992(7) 0.0464(4) Uani d . 1 . . O
    C1 0.84417(18) 1.0060(2) 0.91665(10) 0.0360(4) Uani d . 1 . . C
    C2 0.78117(18) 1.1171(2) 0.97772(11) 0.0355(4) Uani d . 1 . . C
    C3 0.73641(18) 1.0493(2) 1.05455(10) 0.0347(4) Uani d . 1 . . C
    C4 0.75796(18) 0.8652(2) 1.07244(10) 0.0344(4) Uani d . 1 . . C
    C5 0.82038(18) 0.7543(2) 1.01232(10) 0.0360(4) Uani d . 1 . . C
    H5 0.8334 0.6321 1.0246 0.043 Uiso calc R 1 . . H
    C6 0.86381(17) 0.8208(2) 0.93433(11) 0.0362(4) Uani d . 1 . . C
    C7 0.8869(2) 1.0905(3) 0.83628(13) 0.0536(5) Uani d . 1 . . C
    H7 0.8822 1.2161 0.8338 0.064 Uiso calc R 1 . . H
    C8 0.6294(2) 1.3537(3) 0.92771(15) 0.0657(6) Uani d . 1 . . C
    H8A 0.6117 1.2961 0.8733 0.099 Uiso calc R 1 . . H
    H8B 0.6274 1.4827 0.9204 0.099 Uiso calc R 1 . . H
    H8C 0.5559 1.3183 0.9660 0.099 Uiso calc R 1 . . H
    C9 0.5329(2) 1.1366(3) 1.13409(13) 0.0569(6) Uani d . 1 . . C
    H9A 0.4741 1.1285 1.0822 0.085 Uiso calc R 1 . . H
    H9B 0.5001 1.2356 1.1680 0.085 Uiso calc R 1 . . H
    H9C 0.5256 1.0259 1.1657 0.085 Uiso calc R 1 . . H
    C10 0.7364(2) 0.6215(3) 1.17200(12) 0.0563(6) Uani d . 1 . . C
    H10A 0.6881 0.5468 1.1295 0.084 Uiso calc R 1 . . H
    H10B 0.6969 0.5986 1.2268 0.084 Uiso calc R 1 . . H
    H10C 0.8381 0.5940 1.1745 0.084 Uiso calc R 1 . . H
    C11 0.9311(2) 0.6907(3) 0.87325(12) 0.0526(5) Uani d . 1 . . C
    H11A 0.9417 0.5742 0.9000 0.079 Uiso calc R 1 . . H
    H11B 1.0245 0.7349 0.8585 0.079 Uiso calc R 1 . . H
    H11C 0.8699 0.6800 0.8224 0.079 Uiso calc R 1 . . H
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
    O1 0.1234(15) 0.0748(12) 0.0537(9) 0.0023(10) 0.0356(9) 0.0043(8)
    O2 0.0505(8) 0.0289(7) 0.0594(8) -0.0021(5) -0.0023(6) 0.0041(6)
    O3 0.0481(8) 0.0391(7) 0.0482(7) -0.0006(6) 0.0080(6) -0.0137(6)
    O4 0.0600(9) 0.0414(8) 0.0383(7) 0.0038(6) 0.0086(6) 0.0053(6)
    C1 0.0352(10) 0.0356(10) 0.0371(9) -0.0056(7) 0.0017(8) 0.0011(7)
    C2 0.0355(10) 0.0267(9) 0.0438(10) -0.0039(7) -0.0026(8) 0.0011(8)
    C3 0.0341(9) 0.0326(10) 0.0371(9) -0.0018(7) 0.0009(7) -0.0070(7)
    C4 0.0351(10) 0.0344(10) 0.0336(9) -0.0025(7) -0.0009(7) 0.0024(7)
    C5 0.0380(10) 0.0274(9) 0.0426(10) 0.0016(7) 0.0008(8) 0.0018(7)
    C6 0.0320(9) 0.0363(10) 0.0403(10) -0.0020(7) 0.0022(7) -0.0056(8)
    C7 0.0619(14) 0.0480(12) 0.0519(12) -0.0033(10) 0.0133(10) 0.0047(10)
    C8 0.0664(15) 0.0439(13) 0.0854(16) 0.0065(10) -0.0135(12) 0.0110(11)
    C9 0.0528(14) 0.0591(14) 0.0594(13) 0.0078(10) 0.0108(10) -0.0120(10)
    C10 0.0716(15) 0.0469(13) 0.0508(11) 0.0065(10) 0.0075(10) 0.0184(10)
    C11 0.0587(13) 0.0459(12) 0.0543(12) 0.0020(9) 0.0142(10) -0.0077(9)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 C7 . 1.194(2) yes
    O2 C2 . 1.380(2) yes
    O2 C8 . 1.422(2) ?
    O3 C3 . 1.3760(19) yes
    O3 C9 . 1.440(2) ?
    O4 C4 . 1.3551(19) yes
    O4 C10 . 1.433(2) ?
    C1 C7 . 1.472(2) yes
    C2 C1 . 1.404(2) ?
    C3 C2 . 1.381(2) ?
    C4 C3 . 1.402(2) ?
    C5 C4 . 1.391(2) ?
    C5 H5 . 0.9300 ?
    C6 C5 . 1.390(2) ?
    C6 C1 . 1.406(2) ?
    C7 H7 . 0.9300 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 C6 . 1.508(2) yes
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 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 O2 C8 . . 114.36(14) yes
    C3 O3 C9 . . 115.72(13) yes
    C4 O4 C10 . . 118.34(14) yes
    C2 C1 C6 . . 119.24(15) ?
    C2 C1 C7 . . 117.82(16) ?
    C6 C1 C7 . . 122.93(16) ?
    O2 C2 C3 . . 118.64(15) ?
    O2 C2 C1 . . 119.46(15) ?
    C3 C2 C1 . . 121.86(16) ?
    O3 C3 C2 . . 119.18(15) ?
    O3 C3 C4 . . 121.93(15) ?
    C2 C3 C4 . . 118.73(15) ?
    O4 C4 C5 . . 124.35(15) ?
    O4 C4 C3 . . 115.89(14) ?
    C5 C4 C3 . . 119.76(15) ?
    C6 C5 C4 . . 121.88(16) ?
    C6 C5 H5 . . 119.1 ?
    C4 C5 H5 . . 119.1 ?
    C5 C6 C1 . . 118.51(15) ?
    C5 C6 C11 . . 118.18(16) ?
    C1 C6 C11 . . 123.31(16) ?
    O1 C7 C1 . . 127.1(2) yes
    O1 C7 H7 . . 116.5 ?
    C1 C7 H7 . . 116.5 ?
    O2 C8 H8C . . 109.5 ?
    O2 C8 H8A . . 109.5 ?
    O2 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    O3 C9 H9A . . 109.5 ?
    O3 C9 H9B . . 109.5 ?
    O3 C9 H9C . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    O4 C10 H10A . . 109.5 ?
    O4 C10 H10B . . 109.5 ?
    O4 C10 H10C . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C6 C11 H11A . . 109.5 ?
    C6 C11 H11B . . 109.5 ?
    C6 C11 H11C . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 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
    C1 C6 C5 C4 . . . . 0.3(2) ?
    C11 C6 C5 C4 . . . . 179.74(16) ?
    C10 O4 C4 C5 . . . . -0.1(2) yes
    C10 O4 C4 C3 . . . . -179.49(15) ?
    C6 C5 C4 O4 . . . . -178.86(15) ?
    C6 C5 C4 C3 . . . . 0.5(2) ?
    C9 O3 C3 C2 . . . . 117.23(18) ?
    C9 O3 C3 C4 . . . . -67.5(2) yes
    O4 C4 C3 O3 . . . . 2.7(2) ?
    C5 C4 C3 O3 . . . . -176.77(15) ?
    O4 C4 C3 C2 . . . . 178.00(14) ?
    C5 C4 C3 C2 . . . . -1.4(2) ?
    C8 O2 C2 C3 . . . . -85.60(19) yes
    C8 O2 C2 C1 . . . . 96.55(19) ?
    O3 C3 C2 O2 . . . . -0.8(2) ?
    C4 C3 C2 O2 . . . . -176.28(15) ?
    O3 C3 C2 C1 . . . . 176.98(15) ?
    C4 C3 C2 C1 . . . . 1.5(2) ?
    O2 C2 C1 C6 . . . . 177.12(15) ?
    C3 C2 C1 C6 . . . . -0.7(2) ?
    O2 C2 C1 C7 . . . . -2.9(2) ?
    C3 C2 C1 C7 . . . . 179.34(15) ?
    C5 C6 C1 C2 . . . . -0.3(2) ?
    C11 C6 C1 C2 . . . . -179.66(16) ?
    C5 C6 C1 C7 . . . . 179.73(16) ?
    C11 C6 C1 C7 . . . . 0.3(3) ?
    C2 C1 C7 O1 . . . . -171.3(2) ?
    C6 C1 C7 O1 . . . . 8.7(3) yes
