#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/16/2011658.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_2011658
loop_
_publ_author_name
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
'Razak, Ibrahim Abdul'
'Saewon, Nisakorn'
'Karalai, Chatchanok'
'Chantrapromma, Kan'
_publ_section_title
;
 2-(4-Acetyl-3,5-dihydroxy-2-methylphenoxy)-4,6-dimethoxy-3-methylbenzoic
 acid
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e598
_journal_page_last               e599
_journal_paper_doi               10.1107/S0108270100016280
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C19 H20 O8'
_chemical_formula_weight         376.35
_chemical_melting_point          175.0(10)
_chemical_name_systematic
;
2-(4-Acetyl-3,5-dihydroxy-2-methylphenoxy)-4,6-dimethoxy-3-methylbenzoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.9280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0228(3)
_cell_length_b                   24.7920(10)
_cell_length_c                   12.1890(10)
_cell_measurement_reflns_used    3937
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      1.64
_cell_volume                     1787.02(19)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_publication_material  'SHELXTL and PLATON (Spek, 1990)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .904
_diffrn_measured_fraction_theta_max .904
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0753
_diffrn_reflns_av_sigmaI/netI    .1018
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6669
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          .34
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .10
_refine_diff_density_max         .47
_refine_diff_density_min         -.36
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .961
_refine_ls_R_factor_all          .136
_refine_ls_R_factor_gt           .080
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1483P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .231
_reflns_number_gt                1529
_reflns_number_total             2848
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0457.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '174-176' was changed to '175.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '174-176' was changed to '175.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1787.1(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2011658
_cod_database_fobs_code          2011658
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'
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 1.1912(5) .58748(10) .2336(2) .0408(8) Uani d . 1 . . O
O2 .5518(6) .65014(13) -.0280(3) .0714(12) Uani d . 1 . . O
H2A .5548 .6186 -.0477 .107 Uiso calc R 1 . . H
O3 .6996(7) .80722(13) .0786(3) .0742(12) Uani d . 1 . . O
O4 1.0595(7) .77311(12) .1958(3) .0718(12) Uani d . 1 . . O
H4A .9642 .7950 .1667 .108 Uiso calc R 1 . . H
O5 .6954(6) .48547(12) .4075(3) .0585(10) Uani d . 1 . . O
O6 1.1350(5) .39835(11) .1675(3) .0469(9) Uani d . 1 . . O
O7 1.4470(5) .46170(12) .1015(3) .0482(9) Uani d . 1 . . O
O8 1.2700(6) .53787(13) .0455(3) .0613(10) Uani d . 1 . . O
H8A 1.3684 .5390 .0074 .092 Uiso calc R 1 . . H
C1 .8631(8) .61821(17) .1042(4) .0462(12) Uani d . 1 . . C
H1A .8223 .5829 .0843 .055 Uiso calc R 1 . . H
C2 .7321(8) .66010(17) .0563(4) .0486(13) Uani d . 1 . . C
C3 .7823(8) .71442(16) .0875(4) .0422(12) Uani d . 1 . . C
C4 .9890(8) .72245(16) .1640(4) .0442(12) Uani d . 1 . . C
C5 1.1305(8) .68091(16) .2101(4) .0425(12) Uani d . 1 . . C
C6 1.0567(8) .62856(16) .1827(4) .0402(11) Uani d . 1 . . C
C7 1.0854(7) .53831(15) .2480(4) .0336(10) Uani d . 1 . . C
C8 .9357(7) .53618(16) .3208(4) .0400(11) Uani d . 1 . . C
C9 .8464(7) .48542(17) .3387(4) .0396(11) Uani d . 1 . . C
C10 .9128(7) .43905(16) .2901(4) .0402(11) Uani d . 1 . . C
H10A .8545 .4057 .3052 .048 Uiso calc R 1 . . H
C11 1.0657(7) .44248(16) .2190(4) .0359(10) Uani d . 1 . . C
C12 1.1536(7) .49248(15) .1943(3) .0323(10) Uani d . 1 . . C
C13 .6371(9) .76068(18) .0483(4) .0543(14) Uani d . 1 . . C
C14 .4080(10) .7549(2) -.0252(5) .0721(17) Uani d . 1 . . C
H14A .3408 .7899 -.0401 .108 Uiso calc R 1 . . H
H14B .3133 .7330 .0119 .108 Uiso calc R 1 . . H
H14C .4236 .7381 -.0943 .108 Uiso calc R 1 . . H
C15 1.3484(9) .6915(2) .2918(5) .0708(17) Uani d . 1 . . C
H15A 1.3722 .7297 .2999 .106 Uiso calc R 1 . . H
H15B 1.4723 .6755 .2643 .106 Uiso calc R 1 . . H
H15C 1.3389 .6760 .3630 .106 Uiso calc R 1 . . H
C16 .8672(9) .58493(18) .3812(4) .0535(13) Uani d . 1 . . C
H16A .9421 .6164 .3601 .080 Uiso calc R 1 . . H
H16B .9095 .5796 .4604 .080 Uiso calc R 1 . . H
H16C .7064 .5898 .3614 .080 Uiso calc R 1 . . H
C17 .5833(9) .43585(19) .4250(5) .0658(16) Uani d . 1 . . C
H17A .4812 .4420 .4754 .099 Uiso calc R 1 . . H
H17B .6937 .4094 .4564 .099 Uiso calc R 1 . . H
H17C .5001 .4230 .3549 .099 Uiso calc R 1 . . H
C18 1.0217(9) .34841(17) .1762(5) .0560(14) Uani d . 1 . . C
H18A 1.0858 .3210 .1362 .084 Uiso calc R 1 . . H
H18B .8639 .3524 .1449 .084 Uiso calc R 1 . . H
H18C 1.0393 .3383 .2534 .084 Uiso calc R 1 . . H
C19 1.3050(8) .49644(16) .1123(4) .0384(11) Uani d . 1 . . C
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
C6 O1 C7 117.3(3) yes
C2 O2 H2A 109.5 ?
C4 O4 H4A 109.5 ?
C9 O5 C17 118.8(4) yes
C11 O6 C18 117.9(3) yes
C19 O8 H8A 109.5 ?
C2 C1 C6 119.8(4) ?
C2 C1 H1A 120.1 ?
C6 C1 H1A 120.1 ?
C1 C2 O2 119.7(4) ?
C1 C2 C3 122.1(4) ?
O2 C2 C3 118.1(4) ?
C2 C3 C4 115.2(4) ?
C2 C3 C13 124.9(4) ?
C4 C3 C13 119.9(4) ?
O4 C4 C5 115.9(4) ?
O4 C4 C3 120.3(4) ?
C5 C4 C3 123.8(4) ?
C4 C5 C6 116.9(4) ?
C4 C5 C15 121.9(4) ?
C6 C5 C15 121.2(4) ?
O1 C6 C1 121.5(4) ?
O1 C6 C5 116.7(4) ?
C1 C6 C5 121.8(4) ?
C8 C7 O1 118.8(4) ?
C8 C7 C12 123.4(4) ?
O1 C7 C12 117.6(4) ?
C7 C8 C9 116.8(4) ?
C7 C8 C16 123.6(4) ?
C9 C8 C16 119.6(4) ?
O5 C9 C10 123.3(4) ?
O5 C9 C8 114.8(4) ?
C10 C9 C8 121.8(4) ?
C11 C10 C9 119.8(4) ?
C11 C10 H10A 120.1 ?
C9 C10 H10A 120.1 ?
O6 C11 C10 122.5(4) ?
O6 C11 C12 116.6(4) ?
C10 C11 C12 120.8(4) ?
C11 C12 C7 117.2(4) ?
C11 C12 C19 120.7(4) ?
C7 C12 C19 122.1(4) ?
O3 C13 C3 120.0(5) ?
O3 C13 C14 117.1(4) ?
C3 C13 C14 122.9(4) ?
C13 C14 H14A 109.5 ?
C13 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C13 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C5 C15 H15A 109.5 ?
C5 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C5 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C8 C16 H16A 109.5 ?
C8 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C8 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
O5 C17 H17A 109.5 ?
O5 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
O5 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
O6 C18 H18A 109.5 ?
O6 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
O6 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
O7 C19 O8 121.0(4) ?
O7 C19 C12 123.6(4) ?
O8 C19 C12 115.3(4) ?
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 C6 . 1.374(5) yes
O1 C7 . 1.402(5) yes
O2 C2 . 1.369(6) yes
O2 H2A . .8200 ?
O3 C13 . 1.248(5) yes
O4 C4 . 1.358(5) yes
O4 H4A . .8200 ?
O5 C9 . 1.349(5) yes
O5 C17 . 1.438(5) yes
O6 C11 . 1.366(5) yes
O6 C18 . 1.427(5) yes
O7 C19 . 1.239(5) yes
O8 C19 . 1.303(5) yes
O8 H8A . .8200 ?
C1 C2 . 1.366(6) ?
C1 C6 . 1.385(6) ?
C1 H1A . .9300 ?
C2 C3 . 1.416(6) ?
C3 C4 . 1.421(7) ?
C3 C13 . 1.466(6) ?
C4 C5 . 1.386(6) ?
C5 C6 . 1.392(6) ?
C5 C15 . 1.512(7) ?
C7 C8 . 1.381(6) ?
C7 C12 . 1.411(6) ?
C8 C9 . 1.402(6) ?
C8 C16 . 1.512(6) ?
C9 C10 . 1.387(6) ?
C10 C11 . 1.381(6) ?
C10 H10A . .9300 ?
C11 C12 . 1.403(6) ?
C12 C19 . 1.478(6) ?
C13 C14 . 1.503(8) ?
C14 H14A . .9600 ?
C14 H14B . .9600 ?
C14 H14C . .9600 ?
C15 H15A . .9600 ?
C15 H15B . .9600 ?
C15 H15C . .9600 ?
C16 H16A . .9600 ?
C16 H16B . .9600 ?
C16 H16C . .9600 ?
C17 H17A . .9600 ?
C17 H17B . .9600 ?
C17 H17C . .9600 ?
C18 H18A . .9600 ?
C18 H18B . .9600 ?
C18 H18C . .9600 ?
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
_geom_hbond_publ_flag
O2 H2A O7 3_765 .82 2.10 2.914(4) 178 yes
O4 H4A O3 1_555 .82 1.77 2.506(6) 148 yes
O8 H8A O7 3_865 .82 1.89 2.697(5) 170 yes
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
_geom_torsion_publ_flag
C6 C1 C2 O2 174.4(4) yes
C6 C1 C2 C3 -2.7(7) ?
C1 C2 C3 C4 5.6(7) yes
O2 C2 C3 C4 -171.5(4) ?
C1 C2 C3 C13 -173.3(4) ?
O2 C2 C3 C13 9.6(7) yes
C2 C3 C4 O4 177.0(4) yes
C13 C3 C4 O4 -4.1(7) ?
C2 C3 C4 C5 -2.6(7) ?
C13 C3 C4 C5 176.3(4) yes
O4 C4 C5 C6 177.2(4) yes
C3 C4 C5 C6 -3.2(7) ?
O4 C4 C5 C15 .7(7) ?
C3 C4 C5 C15 -179.7(5) ?
C7 O1 C6 C1 -29.9(6) yes
C7 O1 C6 C5 152.9(4) ?
C2 C1 C6 O1 179.2(4) ?
C2 C1 C6 C5 -3.8(7) ?
C4 C5 C6 O1 -176.3(4) yes
C15 C5 C6 O1 .2(7) ?
C4 C5 C6 C1 6.5(7) ?
C15 C5 C6 C1 -177.0(5) ?
C6 O1 C7 C8 -67.2(5) ?
C6 O1 C7 C12 118.3(4) ?
O1 C7 C8 C9 -175.6(4) ?
C12 C7 C8 C9 -1.4(6) ?
O1 C7 C8 C16 4.0(6) ?
C12 C7 C8 C16 178.2(4) ?
C17 O5 C9 C10 -5.1(7) yes
C17 O5 C9 C8 175.9(4) yes
C7 C8 C9 O5 -178.0(4) ?
C16 C8 C9 O5 2.5(6) ?
C7 C8 C9 C10 3.0(6) ?
C16 C8 C9 C10 -176.5(4) ?
O5 C9 C10 C11 179.0(4) ?
C8 C9 C10 C11 -2.1(7) ?
C18 O6 C11 C10 8.6(6) yes
C18 O6 C11 C12 -169.9(4) ?
C9 C10 C11 O6 -179.1(4) yes
C9 C10 C11 C12 -.6(7) ?
O6 C11 C12 C7 -179.3(4) ?
C10 C11 C12 C7 2.2(6) ?
O6 C11 C12 C19 2.8(6) ?
C10 C11 C12 C19 -175.8(4) ?
C8 C7 C12 C11 -1.2(6) ?
O1 C7 C12 C11 173.1(3) ?
C8 C7 C12 C19 176.7(4) yes
O1 C7 C12 C19 -9.0(6) ?
C2 C3 C13 O3 -178.2(5) ?
C4 C3 C13 O3 3.0(7) ?
C2 C3 C13 C14 3.8(8) yes
C4 C3 C13 C14 -175.0(5) ?
C11 C12 C19 O7 -36.4(6) ?
C7 C12 C19 O7 145.8(4) ?
C11 C12 C19 O8 139.3(4) ?
C7 C12 C19 O8 -38.5(6) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21105825
