##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(Z)-3-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-2-propenoic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H18 O6'
_chemical_formula_sum     'C18 H18 O6'
_chemical_formula_iupac     'C18 H18 O6'
_chemical_formula_weight     330.32
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     8.920(7)
_cell_length_b     12.053(6)
_cell_length_c     15.658(6)
_cell_angle_alpha     90.00
_cell_angle_beta     101.70(4)
_cell_angle_gamma     90.00
_cell_volume     1648.4(16)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     18.55
_cell_measurement_theta_max     23.07
_cell_measurement_temperature     296(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.50
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.331
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     696
_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     ?
_exptl_special_details
;
Data were collected at room temperature using a Rigaku AFC6R diffractometer.
The data were collected using 2θ-ω-scan. Scans of (1.37+0.30tanθ) were made
at a speed of 8.0ο/min in ω. The weak reflections (I<10.0σI) were
rescanned (maximum 3 rescans) and the counts were accumulated to assure good
counting statistics. Stationary bacground counts were recored on each side of
the reflection.The ratio of peak counting time to backgroud counting time was
2:1. The crystal--to--detector distance was 400 mm.
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'normal-focus rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku AFC-6'
_diffrn_measurement_method     '2θ-ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3100
_diffrn_reflns_av_R_equivalents     0.0159
_diffrn_reflns_av_sigmaI/netI     0.0436
_diffrn_reflns_theta_min     2.15
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     3
_diffrn_standards_interval_count     150
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     none
_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     2901
_reflns_number_gt     1919
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0688
_refine_ls_R_factor_gt     0.0345
_refine_ls_wR_factor_gt     0.0859
_refine_ls_wR_factor_ref     0.1012
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     2901
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0335P)²+0.3604P] 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     0.213
_refine_diff_density_min     -0.125
_refine_ls_extinction_method     SHELXTL
_refine_ls_extinction_coef     0.0178(15)
_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
                        'TEXSAN--TEXRAY (Molecular Structure Corporation, 1985)'
_computing_cell_refinement     'TEXSAN--TEXRAY '
_computing_data_reduction     'TEXSAN--TEXRAY '
_computing_structure_solution     'SHELXTL (Bruker, 2001)'
_computing_structure_refinement     'SHELXTL '
_computing_molecular_graphics     'DIAMOND (Brandenburg, 2000)'
_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
    C1 0.09822(19) -0.06378(14) 0.15409(11) 0.0434(4) Uani d . 1 . . C
    C2 0.19625(19) 0.01258(15) 0.12446(12) 0.0450(4) Uani d . 1 . . C
    H2 0.2357 0.0722 0.1597 0.044(5) Uiso calc R 1 . . H
    C3 0.2341(2) -0.00002(15) 0.04427(12) 0.0465(4) Uani d . 1 . . C
    C4 0.1760(2) -0.09056(15) -0.00920(12) 0.0472(4) Uani d . 1 . . C
    C5 0.0789(2) -0.16437(15) 0.01894(12) 0.0492(5) Uani d . 1 . . C
    H5 0.0387 -0.2235 -0.0166 0.044(5) Uiso calc R 1 . . H
    C6 0.0405(2) -0.15131(15) 0.09991(12) 0.0481(5) Uani d . 1 . . C
    H6 -0.0250 -0.2021 0.1181 0.056(6) Uiso calc R 1 . . H
    C7 0.05540(19) -0.05622(15) 0.23897(12) 0.0441(4) Uani d . 1 . . C
    H7 -0.0102 -0.1118 0.2504 0.050(5) Uiso calc R 1 . . H
    C8 0.09545(19) 0.01783(14) 0.30291(11) 0.0430(4) Uani d . 1 . . C
    C9 0.3805(3) 0.1671(2) 0.05904(17) 0.0795(8) Uani d . 1 . . C
    H9A 0.2949 0.2105 0.0684 0.105(10) Uiso calc R 1 . . H
    H9B 0.4415 0.2105 0.0275 0.100(8) Uiso calc R 1 . . H
    H9C 0.4415 0.1456 0.1143 0.109(10) Uiso calc R 1 . . H
    C10 0.1711(3) -0.18840(19) -0.14195(15) 0.0713(6) Uani d . 1 . . C
    H10A 0.0612 -0.1886 -0.1565 0.079(7) Uiso calc R 1 . . H
    H10B 0.2066 -0.2560 -0.1122 0.077(7) Uiso calc R 1 . . H
    H10C 0.2108 -0.1827 -0.1944 0.105(9) Uiso calc R 1 . . H
    C11 0.33326(19) 0.11361(15) 0.33168(11) 0.0433(4) Uani d . 1 . . C
    C12 0.4065(2) 0.21467(16) 0.32813(12) 0.0514(5) Uani d . 1 . . C
    C13 0.5622(2) 0.22145(19) 0.36244(15) 0.0658(6) Uani d . 1 . . C
    H13 0.6134 0.2883 0.3604 0.088(8) Uiso calc R 1 . . H
    C14 0.6415(2) 0.1291(2) 0.39975(16) 0.0707(6) Uani d . 1 . . C
    H14 0.7461 0.1343 0.4223 0.095(8) Uiso calc R 1 . . H
    C15 0.5684(2) 0.0303(2) 0.40394(15) 0.0671(6) Uani d . 1 . . C
    H15 0.6223 -0.0310 0.4301 0.092(8) Uiso calc R 1 . . H
    C16 0.4125(2) 0.02229(17) 0.36861(13) 0.0560(5) Uani d . 1 . . C
    H16 0.3621 -0.0450 0.3701 0.075(7) Uiso calc R 1 . . H
    C17 0.3793(3) 0.40837(19) 0.2980(2) 0.0796(7) Uani d . 1 . . C
    H17A 0.4137 0.4260 0.3586 0.129(12) Uiso calc R 1 . . H
    H17B 0.3027 0.4608 0.2718 0.120(11) Uiso calc R 1 . . H
    H17C 0.4643 0.4116 0.2690 0.113(10) Uiso calc R 1 . . H
    C18 0.0490(2) 0.01075(15) 0.38762(12) 0.0444(4) Uani d . 1 . . C
    O1 0.32630(16) 0.07083(12) 0.01010(9) 0.0636(4) Uani d . 1 . . O
    O2 0.22250(16) -0.09634(12) -0.08689(9) 0.0610(4) Uani d . 1 . . O
    O3 0.17836(13) 0.11280(10) 0.29338(8) 0.0459(3) Uani d . 1 . . O
    O4 0.31587(16) 0.29951(11) 0.28993(10) 0.0716(4) Uani d . 1 . . O
    O5 0.09173(15) 0.08234(11) 0.44459(8) 0.0556(4) Uani d . 1 . . O
    O6 -0.03502(17) -0.07398(11) 0.39865(10) 0.0603(4) Uani d . 1 . . O
    H6A -0.0556 -0.0710 0.4473 0.129(12) Uiso calc R 1 . . H
_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
    C1 C6 . 1.386(2) ?
    C1 C2 . 1.411(2) ?
    C1 C7 . 1.458(3) ?
    C2 C3 . 1.373(3) ?
    C2 H2 . 0.9300 ?
    C3 O1 . 1.368(2) ?
    C3 C4 . 1.409(3) ?
    C4 O2 . 1.364(2) ?
    C4 C5 . 1.375(3) ?
    C5 C6 . 1.388(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.335(2) ?
    C7 H7 . 0.9300 ?
    C8 O3 . 1.387(2) ?
    C8 C18 . 1.470(3) ?
    C9 O1 . 1.421(3) ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 O2 . 1.423(2) ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 C16 . 1.371(3) ?
    C11 C12 . 1.389(3) ?
    C11 O3 . 1.390(2) ?
    C12 O4 . 1.364(2) ?
    C12 C13 . 1.386(3) ?
    C13 C14 . 1.384(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.365(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.392(3) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C17 O4 . 1.424(3) ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C18 O5 . 1.244(2) ?
    C18 O6 . 1.299(2) ?
    O6 H6A . 0.8200 ?
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 . . 118.25(17) ?
    C6 C1 C7 . . 118.17(16) ?
    C2 C1 C7 . . 123.58(17) ?
    C3 C2 C1 . . 120.80(18) ?
    C3 C2 H2 . . 119.6 ?
    C1 C2 H2 . . 119.6 ?
    O1 C3 C2 . . 124.58(17) ?
    O1 C3 C4 . . 115.41(16) ?
    C2 C3 C4 . . 120.01(17) ?
    O2 C4 C5 . . 125.29(17) ?
    O2 C4 C3 . . 115.34(16) ?
    C5 C4 C3 . . 119.37(17) ?
    C4 C5 C6 . . 120.50(18) ?
    C4 C5 H5 . . 119.7 ?
    C6 C5 H5 . . 119.7 ?
    C5 C6 C1 . . 121.05(18) ?
    C5 C6 H6 . . 119.5 ?
    C1 C6 H6 . . 119.5 ?
    C8 C7 C1 . . 130.22(17) ?
    C8 C7 H7 . . 114.9 ?
    C1 C7 H7 . . 114.9 ?
    C7 C8 O3 . . 122.59(16) ?
    C7 C8 C18 . . 123.81(16) ?
    O3 C8 C18 . . 113.51(15) ?
    O1 C9 H9A . . 109.5 ?
    O1 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    O1 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    O2 C10 H10A . . 109.5 ?
    O2 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    O2 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C16 C11 C12 . . 120.96(17) ?
    C16 C11 O3 . . 123.96(16) ?
    C12 C11 O3 . . 115.05(16) ?
    O4 C12 C13 . . 125.72(18) ?
    O4 C12 C11 . . 115.67(17) ?
    C13 C12 C11 . . 118.61(19) ?
    C12 C13 C14 . . 120.2(2) ?
    C12 C13 H13 . . 119.9 ?
    C14 C13 H13 . . 119.9 ?
    C15 C14 C13 . . 120.9(2) ?
    C15 C14 H14 . . 119.6 ?
    C13 C14 H14 . . 119.6 ?
    C14 C15 C16 . . 119.3(2) ?
    C14 C15 H15 . . 120.3 ?
    C16 C15 H15 . . 120.3 ?
    C11 C16 C15 . . 120.0(2) ?
    C11 C16 H16 . . 120.0 ?
    C15 C16 H16 . . 120.0 ?
    O4 C17 H17A . . 109.5 ?
    O4 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    O4 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    O5 C18 O6 . . 123.46(17) ?
    O5 C18 C8 . . 120.34(16) ?
    O6 C18 C8 . . 116.19(16) ?
    C3 O1 C9 . . 117.71(16) ?
    C4 O2 C10 . . 117.47(16) ?
    C8 O3 C11 . . 117.66(13) ?
    C12 O4 C17 . . 117.54(18) ?
    C18 O6 H6A . . 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 . . . . -0.4(3) ?
    C7 C1 C2 C3 . . . . 179.01(17) ?
    C1 C2 C3 O1 . . . . 179.02(17) ?
    C1 C2 C3 C4 . . . . -0.6(3) ?
    O1 C3 C4 O2 . . . . 1.4(2) ?
    C2 C3 C4 O2 . . . . -179.01(16) ?
    O1 C3 C4 C5 . . . . -178.24(16) ?
    C2 C3 C4 C5 . . . . 1.4(3) ?
    O2 C4 C5 C6 . . . . 179.21(17) ?
    C3 C4 C5 C6 . . . . -1.2(3) ?
    C4 C5 C6 C1 . . . . 0.3(3) ?
    C2 C1 C6 C5 . . . . 0.6(3) ?
    C7 C1 C6 C5 . . . . -178.89(16) ?
    C6 C1 C7 C8 . . . . 179.26(18) ?
    C2 C1 C7 C8 . . . . -0.2(3) ?
    C1 C7 C8 O3 . . . . 7.4(3) ?
    C1 C7 C8 C18 . . . . -176.45(17) ?
    C16 C11 C12 O4 . . . . -179.95(17) ?
    O3 C11 C12 O4 . . . . 1.8(2) ?
    C16 C11 C12 C13 . . . . 0.3(3) ?
    O3 C11 C12 C13 . . . . -178.00(17) ?
    O4 C12 C13 C14 . . . . 179.9(2) ?
    C11 C12 C13 C14 . . . . -0.4(3) ?
    C12 C13 C14 C15 . . . . -0.4(4) ?
    C13 C14 C15 C16 . . . . 1.2(4) ?
    C12 C11 C16 C15 . . . . 0.6(3) ?
    O3 C11 C16 C15 . . . . 178.69(18) ?
    C14 C15 C16 C11 . . . . -1.3(3) ?
    C7 C8 C18 O5 . . . . 179.37(17) ?
    O3 C8 C18 O5 . . . . -4.1(2) ?
    C7 C8 C18 O6 . . . . 0.4(3) ?
    O3 C8 C18 O6 . . . . 176.94(15) ?
    C2 C3 O1 C9 . . . . -3.3(3) ?
    C4 C3 O1 C9 . . . . 176.27(19) ?
    C5 C4 O2 C10 . . . . -2.5(3) ?
    C3 C4 O2 C10 . . . . 177.91(17) ?
    C7 C8 O3 C11 . . . . -103.1(2) ?
    C18 C8 O3 C11 . . . . 80.32(18) ?
    C16 C11 O3 C8 . . . . 8.4(2) ?
    C12 C11 O3 C8 . . . . -173.35(15) ?
    C13 C12 O4 C17 . . . . -10.7(3) ?
    C11 C12 O4 C17 . . . . 169.55(19) ?
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
    O6 H6A O5 3_556 0.82 1.79 2.607(2) 173
    C2 H2 O3 . 0.93 2.31 2.941(2) 125
    C7 H7 O6 . 0.93 2.42 2.787(2) 103
data_global
_journal_date_recd_electronic     2003-12-11
_journal_date_accepted     2003-12-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue      2
_journal_page_first     o165
_journal_page_last     o167
_journal_paper_category     EO
_publ_contact_author_name     'Vratislav Langer'
_publ_contact_author_address
;
Department of Environmental Inorganic Chemistry
Chalmers University of Technology
SE-41296 Göteborg
Sweden
;
_publ_contact_author_email     'langer@chem.chalmers.se'
_publ_contact_author_fax     '46-31-7722853'
_publ_contact_author_phone     '46-31-7722877'
_publ_section_title
;
(Z)-3-(3,4-Dimethoxyphenyl)-2-(2-methoxyphenoxy)-2-propenoic acid
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Langer, Vratislav'
; ?
;
;
Department of Environmental Inorganic Chemistry
Chalmers University of Technology
SE-412 96 Göteborg
Sweden
;
    'Li, Shiming'
; ?
;
;
Department of Forest Products and Chemical Engineering
Chalmers University of Technology
SE-412 96 Göteborg
Sweden
;
    'Lundquist, Knut'
; ?
;
;
Department of Forest Products and Chemical Engineering
Chalmers University of Technology
SE-412 96 Göteborg
Sweden
;
    'Stomberg, Rolf'
; ?
;
;
Department of Chemistry
Division of Inorganic Chemistry
Göteborg University
SE-412 96 Göteborg
Sweden
;
