#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2203200.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2203200
loop_
_publ_author_name
'Langer, Vratislav'
'Li, Shiming'
'Lundquist, Knut'
'Stomberg, Rolf'
_publ_section_title
;
(Z)-3-(3,4-Dimethoxyphenyl)-2-(2-methoxyphenoxy)-2-propenoic acid
;
_journal_issue                 2
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o165
_journal_page_last             o167
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C18 H18 O6'
_chemical_formula_moiety       'C18 H18 O6'
_chemical_formula_sum          'C18 H18 O6'
_chemical_formula_weight       330.32
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
(Z)-3-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-2-propenoic acid
;
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         SHELXL-97
_cell_angle_alpha              90.00
_cell_angle_beta               101.70(4)
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 8.920(7)
_cell_length_b                 12.053(6)
_cell_length_c                 15.658(6)
_cell_measurement_reflns_used  25
_cell_measurement_temperature  296(2)
_cell_measurement_theta_max    23.07
_cell_measurement_theta_min    18.55
_cell_volume                   1648.4(16)
_computing_cell_refinement     'TEXSAN--TEXRAY '
_computing_data_collection
'TEXSAN--TEXRAY (Molecular Structure Corporation, 1985)'
_computing_data_reduction      'TEXSAN--TEXRAY '
_computing_molecular_graphics  'DIAMOND (Brandenburg, 2000)'
_computing_publication_material 'SHELXTL '
_computing_structure_refinement 'SHELXTL '
_computing_structure_solution  'SHELXTL (Bruker, 2001)'
_diffrn_ambient_temperature    296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type 'Rigaku AFC-6'
_diffrn_measurement_method     2\q-\w
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source       'normal-focus rotating anode'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71069
_diffrn_reflns_av_R_equivalents 0.0159
_diffrn_reflns_av_sigmaI/netI  0.0436
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_l_max     18
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_number          3100
_diffrn_reflns_theta_full      25.00
_diffrn_reflns_theta_max       25.00
_diffrn_reflns_theta_min       2.15
_diffrn_standards_decay_%      none
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time ?
_diffrn_standards_number       3
_exptl_absorpt_coefficient_mu  0.100
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_crystal_colour          'light yellow'
_exptl_crystal_density_diffrn  1.331
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           696
_exptl_crystal_size_max        0.60
_exptl_crystal_size_mid        0.50
_exptl_crystal_size_min        0.30
_refine_diff_density_max       0.213
_refine_diff_density_min       -0.125
_refine_ls_extinction_coef     0.0178(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method   SHELXTL
_refine_ls_goodness_of_fit_ref 1.041
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_parameters   240
_refine_ls_number_reflns       2901
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.041
_refine_ls_R_factor_all        0.0688
_refine_ls_R_factor_gt         0.0345
_refine_ls_shift/su_max        0.001
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.3604P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.0859
_refine_ls_wR_factor_ref       0.1012
_reflns_number_gt              1919
_reflns_number_total           2901
_reflns_threshold_expression   I>2\s(I)
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'
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
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
C1 0.0377(9) 0.0434(10) 0.0473(10) 0.0015(8) 0.0045(8) 0.0046(8)
C2 0.0407(10) 0.0458(10) 0.0473(10) -0.0012(8) 0.0066(8) -0.0003(8)
C3 0.0405(9) 0.0493(11) 0.0497(10) 0.0008(8) 0.0095(8) 0.0044(8)
C4 0.0459(10) 0.0489(11) 0.0456(10) 0.0095(9) 0.0061(8) 0.0017(8)
C5 0.0488(11) 0.0441(10) 0.0520(11) 0.0006(9) 0.0040(9) -0.0035(9)
C6 0.0449(10) 0.0441(10) 0.0537(11) -0.0003(9) 0.0062(9) 0.0028(8)
C7 0.0373(9) 0.0447(10) 0.0503(10) -0.0002(8) 0.0084(8) 0.0061(8)
C8 0.0375(9) 0.0437(10) 0.0477(10) -0.0019(8) 0.0086(8) 0.0053(8)
C9 0.0874(18) 0.0756(16) 0.0825(18) -0.0362(15) 0.0336(16) -0.0110(14)
C10 0.0863(19) 0.0669(15) 0.0627(14) 0.0026(13) 0.0201(13) -0.0165(12)
C11 0.0385(9) 0.0526(11) 0.0391(9) -0.0030(8) 0.0088(7) -0.0042(8)
C12 0.0478(11) 0.0528(12) 0.0535(11) -0.0056(9) 0.0100(9) -0.0021(9)
C13 0.0487(12) 0.0647(14) 0.0818(15) -0.0143(11) 0.0080(11) -0.0081(12)
C14 0.0440(12) 0.0793(16) 0.0842(16) -0.0040(12) 0.0024(11) -0.0125(13)
C15 0.0496(12) 0.0698(15) 0.0777(15) 0.0077(11) 0.0028(11) -0.0002(12)
C16 0.0452(11) 0.0564(12) 0.0654(13) -0.0010(10) 0.0087(9) 0.0026(10)
C17 0.0782(17) 0.0530(14) 0.109(2) -0.0128(13) 0.0231(16) 0.0118(14)
C18 0.0383(9) 0.0438(10) 0.0517(11) 0.0015(8) 0.0099(8) 0.0031(9)
O1 0.0675(9) 0.0671(9) 0.0620(9) -0.0190(8) 0.0272(7) -0.0070(7)
O2 0.0701(9) 0.0637(9) 0.0533(8) -0.0008(7) 0.0220(7) -0.0089(7)
O3 0.0393(6) 0.0470(7) 0.0501(7) -0.0046(6) 0.0060(5) 0.0052(6)
O4 0.0592(9) 0.0513(9) 0.0983(12) -0.0099(7) 0.0016(8) 0.0104(8)
O5 0.0628(8) 0.0533(8) 0.0546(8) -0.0068(7) 0.0207(7) -0.0058(6)
O6 0.0694(9) 0.0572(8) 0.0606(9) -0.0157(7) 0.0282(7) -0.0023(7)
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'
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_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_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
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) ?