#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012292.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012292
loop_
_publ_author_name
'Gales, Luis'
'de Sousa, Maria Emilia'
'Pinto, Madalena M. M.'
'Kijjoa, Anake'
'Damas, Ana M.'
_publ_section_title
;
 Naturally occurring 1,2,8-trimethoxyxanthone and biphenyl ether
 intermediates leading to 1,2-dimethoxyxanthone
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1319
_journal_page_last               1323
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C16 H16 O5'
_chemical_formula_sum            'C16 H16 O5'
_chemical_formula_weight         288.29
_chemical_melting_point          .335E-305
_chemical_name_systematic
;
Methyl 2-(3,4-dimethoxyphenoxy)benzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 132.31(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.306(7)
_cell_length_b                   7.788(4)
_cell_length_c                   16.426(7)
_cell_measurement_reflns_used    1232
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      5.04
_cell_volume                     1448.0(14)
_computing_cell_refinement       IPDS
_computing_data_collection       'IPDS (Stoe & Cie, 1994)'
_computing_data_reduction        IPDS
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 and ORTEP-3'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .976
_diffrn_measured_fraction_theta_max .976
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'Image Plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .068
_diffrn_reflns_av_sigmaI/netI    .043
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13194
_diffrn_reflns_theta_full        28.10
_diffrn_reflns_theta_max         28.10
_diffrn_reflns_theta_min         5.04
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    .098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'square prism'
_exptl_crystal_F_000             608
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .20
_refine_diff_density_max         .23
_refine_diff_density_min         -.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          .091
_refine_ls_R_factor_gt           .055
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.068P)^2^+0.376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .165
_reflns_number_gt                2221
_reflns_number_total             3439
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm1457.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        1448.0(12)
_cod_database_code               2012292
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_occupancy
_atom_site_type_symbol
O1 .24922(13) .95469(19) .36254(10) .0701(5) Uani d 1 O
O2 .52741(18) 1.1418(3) .67270(13) .1062(8) Uani d 1 O
O3 .43905(15) .9146(2) .56698(12) .0799(5) Uani d 1 O
O4 .08949(12) .7792(2) .00103(11) .0648(4) Uani d 1 O
O5 -.10491(12) .6765(2) -.05112(10) .0647(4) Uani d 1 O
C1 .27071(16) 1.1278(3) .37561(14) .0511(4) Uani d 1 C
C2 .36879(16) 1.1880(3) .48176(15) .0532(4) Uani d 1 C
C3 .3895(2) 1.3644(3) .49603(19) .0668(6) Uani d 1 C
C4 .3174(2) 1.4790(3) .4103(2) .0730(6) Uani d 1 C
C5 .2212(2) 1.4168(3) .30683(19) .0649(5) Uani d 1 C
C6 .19786(18) 1.2434(3) .28934(16) .0563(5) Uani d 1 C
C1' .15623(18) .8911(3) .25623(14) .0586(5) Uani d 1 C
C2' .17351(18) .8712(3) .18365(15) .0575(5) Uani d 1 C
C3' .08389(16) .8010(2) .08024(14) .0522(4) Uani d 1 C
C4' -.02158(16) .7463(3) .05170(14) .0534(5) Uani d 1 C
C5' -.03561(19) .7676(3) .12593(16) .0616(5) Uani d 1 C
C6' .0536(2) .8416(3) .22907(16) .0636(5) Uani d 1 C
C7 .45267(17) 1.0809(3) .58277(15) .0580(5) Uani d 1 C
C8 .1928(3) .8416(4) .0255(3) .0776(7) Uani d 1 C
C9 -.2103(2) .6147(4) -.0804(2) .0687(6) Uani d 1 C
C10 .5178(3) .8075(5) .6633(2) .0852(8) Uani d 1 C
H3 .460(2) 1.401(3) .572(2) .079(7) Uiso d 1 H
H4 .336(2) 1.602(4) .424(2) .088(8) Uiso d 1 H
H5 .167(2) 1.495(3) .246(2) .075(7) Uiso d 1 H
H6 .134(2) 1.201(3) .2192(19) .067(6) Uiso d 1 H
H2' .244(2) .902(3) .2046(18) .066(6) Uiso d 1 H
H5' -.108(2) .731(3) .105(2) .073(7) Uiso d 1 H
H6' .044(2) .854(3) .2804(19) .072(6) Uiso d 1 H
H8A -.252(2) .556(3) -.151(2) .086(8) Uiso d 1 H
H8B -.254(2) .715(4) -.084(2) .079(7) Uiso d 1 H
H8C -.190(2) .531(3) -.025(2) .074(7) Uiso d 1 H
H9A .181(3) .818(4) -.040(3) .110(10) Uiso d 1 H
H9B .262(3) .777(4) .091(2) .092(9) Uiso d 1 H
H9C .205(3) .969(4) .042(2) .096(9) Uiso d 1 H
H10A .505(4) .841(6) .710(3) .153(16) Uiso d 1 H
H10B .594(4) .830(5) .699(3) .133(13) Uiso d 1 H
H10C .494(4) .694(6) .640(3) .156(16) Uiso d 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 .0700(9) .0592(9) .0393(7) -.0049(7) .0198(7) -.0001(6)
O2 .0953(14) .0945(14) .0488(9) .0103(10) .0160(9) -.0106(8)
O3 .0726(10) .0693(10) .0459(7) .0002(8) .0188(7) .0077(7)
O4 .0586(8) .0822(10) .0578(8) -.0099(7) .0409(7) -.0071(7)
O5 .0508(7) .0875(10) .0450(7) -.0137(7) .0279(6) -.0088(7)
C1 .0484(9) .0586(11) .0441(9) .0014(8) .0302(8) -.0011(8)
C2 .0470(9) .0632(11) .0480(9) .0010(8) .0315(8) -.0019(8)
C3 .0608(12) .0680(13) .0596(12) -.0046(10) .0356(10) -.0085(10)
C4 .0787(15) .0574(13) .0778(15) -.0022(11) .0505(13) -.0036(11)
C5 .0685(13) .0639(13) .0645(12) .0128(10) .0457(11) .0107(10)
C6 .0533(10) .0653(12) .0465(10) .0054(9) .0320(9) .0041(8)
C1' .0565(11) .0567(11) .0392(9) .0012(8) .0227(8) .0024(7)
C2' .0466(10) .0581(11) .0510(10) -.0022(8) .0260(8) .0031(8)
C3' .0499(9) .0553(10) .0441(9) .0015(8) .0286(8) .0021(7)
C4' .0468(9) .0608(11) .0409(9) -.0004(8) .0248(8) .0015(8)
C5' .0514(11) .0782(14) .0503(10) -.0023(10) .0323(9) .0017(9)
C6' .0650(12) .0744(14) .0472(10) .0019(10) .0361(10) .0020(9)
C7 .0469(9) .0748(13) .0436(9) .0021(9) .0269(8) -.0064(9)
C8 .0762(16) .0856(19) .0892(18) -.0148(14) .0630(15) -.0064(15)
C9 .0535(11) .0801(16) .0600(13) -.0126(11) .0331(10) -.0059(12)
C10 .0695(16) .088(2) .0566(13) .0065(14) .0256(12) .0197(13)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
_geom_angle_publ_flag
C1 O1 C1' 118.49(15) no
C3' O4 C8 117.06(18) no
C4' O5 C9 117.00(17) no
C7 O3 C10 116.7(2) no
C6' C1' C2' 121.82(18) no
C6' C1' O1 119.00(19) no
C2' C1' O1 119.07(19) no
C3' C2' C1' 119.4(2) no
C3' C2' H2' 120.3(14) no
C1' C2' H2' 120.3(14) no
O4 C3' C2' 124.63(18) no
O4 C3' C4' 115.85(16) no
C2' C3' C4' 119.52(18) no
O5 C4' C5' 124.52(18) no
O5 C4' C3' 115.94(17) no
C5' C4' C3' 119.54(18) no
C4' C5' C6' 120.9(2) no
C4' C5' H5' 118.5(14) no
C6' C5' H5' 120.6(14) no
C1' C6' C5' 118.8(2) no
C1' C6' H6' 120.8(14) no
C5' C6' H6' 120.3(14) no
O1 C1 C6 122.28(17) no
O1 C1 C2 117.67(16) no
C6 C1 C2 120.03(19) no
C3 C2 C1 117.90(18) no
C3 C2 C7 115.82(18) no
C1 C2 C7 126.26(19) no
C4 C3 C2 122.0(2) no
C4 C3 H3 122.7(15) no
C2 C3 H3 115.3(15) no
C3 C4 C5 119.0(2) no
C3 C4 H4 119.0(16) no
C5 C4 H4 122.0(16) no
C6 C5 C4 120.7(2) no
C6 C5 H5 118.6(15) no
C4 C5 H5 120.7(15) no
C5 C6 C1 120.3(2) no
C5 C6 H6 120.7(14) no
C1 C6 H6 119.0(14) no
O4 C8 H9A 106.1(19) no
O4 C8 H9B 107.9(17) no
H9A C8 H9B 111(2) no
O4 C8 H9C 112.0(17) no
H9A C8 H9C 110(2) no
H9B C8 H9C 109(2) no
O5 C9 H8A 104.1(16) no
O5 C9 H8B 108.6(15) no
H8A C9 H8B 114(2) no
O5 C9 H8C 109.6(15) no
H8A C9 H8C 110(2) no
H8B C9 H8C 110(2) no
O2 C7 O3 121.8(2) no
O2 C7 C2 122.8(2) no
O3 C7 C2 115.42(16) no
O3 C10 H10A 105(3) no
O3 C10 H10B 111(2) no
H10A C10 H10B 107(4) no
O3 C10 H10C 107(3) no
H10A C10 H10C 111(4) no
H10B C10 H10C 115(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.370(3) yes
O1 C1' 1.405(2) yes
O4 C3' 1.371(2) yes
O4 C8 1.429(3) yes
O5 C4' 1.369(2) yes
O5 C9 1.422(3) yes
O2 C7 1.200(2) yes
O3 C7 1.310(3) yes
O3 C10 1.444(3) yes
C1' C6' 1.368(3) yes
C1' C2' 1.393(3) yes
C2' C3' 1.389(3) yes
C2' H2' .92(2) no
C3' C4' 1.410(3) yes
C4' C5' 1.383(3) yes
C5' C6' 1.397(3) yes
C5' H5' .96(3) no
C6' H6' .96(3) no
C1 C6 1.391(3) yes
C1 C2 1.411(3) yes
C2 C3 1.394(3) yes
C2 C7 1.493(3) yes
C3 C4 1.380(3) yes
C3 H3 1.00(3) no
C4 C5 1.387(3) yes
C4 H4 .98(3) no
C5 C6 1.377(3) yes
C5 H5 .97(3) no
C6 H6 .93(2) no
C8 H9A .98(3) no
C8 H9B 1.00(3) no
C8 H9C 1.02(3) no
C9 H8A .99(3) no
C9 H8B 1.00(3) no
C9 H8C .98(3) no
C10 H10A .94(4) no
C10 H10B .90(4) no
C10 H10C .93(5) no