#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/00/2200047.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_2200047
loop_
_publ_author_name
'Karalai, Chatchanok'
'Saewon, Nisakorn'
'Chantrapromma, Kan'
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
'Razak, Ibrahim Abdul'
_publ_section_title
;
 1-[4-(3,5-Dimethoxy-2-methylphenoxy)-2,6-dihydroxy-3-methylphenyl]ethanone
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o18
_journal_page_last               o19
_journal_paper_doi               10.1107/S1600536800018213
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C18 H20 O6'
_chemical_formula_sum            'C18 H20 O6'
_chemical_formula_weight         332.34
_chemical_melting_point          189.5(5)
_chemical_name_systematic
;
1-[4-(3,5-Dimethoxy-2-methylphenoxy)-2,6-dihydroxy-3-methylphenyl]ethanone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.4740(10)
_cell_angle_beta                 90.989(2)
_cell_angle_gamma                98.544(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4228(2)
_cell_length_b                   10.14600(10)
_cell_length_c                   11.3559(3)
_cell_measurement_reflns_used    2684
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      1.84
_cell_volume                     824.70(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_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 .983
_diffrn_measured_fraction_theta_max .983
_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  .0625
_diffrn_reflns_av_sigmaI/netI    .1107
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4715
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    .101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             352
_exptl_crystal_size_max          .44
_exptl_crystal_size_mid          .22
_exptl_crystal_size_min          .18
_refine_diff_density_max         .378
_refine_diff_density_min         -.433
_refine_ls_extinction_coef       .040(9)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          .115
_refine_ls_R_factor_gt           .084
_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)+(0.1109P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .228
_reflns_number_gt                1615
_reflns_number_total             2864
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6004.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '189 - 190' was changed to '189.5(5)'
- 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 '189 - 190' was changed to '189.5(5)'
- 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_database_code               2200047
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 .5200(3) .20725(19) .65299(15) .0415(6) Uani d . 1 . . O
O2 .7590(3) .6820(2) .70228(17) .0489(6) Uani d . 1 . . O
H2A .7433 .6789 .7730 .073 Uiso calc R 1 . . H
O3 .8717(3) .6111(2) .33808(18) .0527(7) Uani d . 1 . . O
O4 .7490(3) .3659(2) .32010(16) .0495(6) Uani d . 1 . . O
H4A .7946 .4356 .2996 .074 Uiso calc R 1 . . H
O5 .8189(3) .1038(2) .98373(18) .0550(7) Uani d . 1 . . O
O6 .2931(3) .3248(2) 1.05203(17) .0487(6) Uani d . 1 . . O
C1 .6446(4) .4466(3) .6810(2) .0353(7) Uani d . 1 . . C
H1A .6201 .4623 .7625 .042 Uiso calc R 1 . . H
C2 .7219(4) .5531(3) .6314(2) .0339(7) Uani d . 1 . . C
C3 .7615(4) .5322(3) .5078(2) .0335(7) Uani d . 1 . . C
C4 .7159(4) .3960(3) .4388(2) .0349(7) Uani d . 1 . . C
C5 .6389(4) .2866(3) .4865(2) .0334(7) Uani d . 1 . . C
C6 .6037(4) .3158(3) .6086(2) .0335(7) Uani d . 1 . . C
C7 .5343(4) .2155(3) .7788(2) .0349(7) Uani d . 1 . . C
C8 .6755(4) .1603(3) .8216(2) .0366(7) Uani d . 1 . . C
C9 .6786(4) .1615(3) .9461(2) .0373(7) Uani d . 1 . . C
C10 .5526(4) .2175(3) 1.0206(2) .0390(7) Uani d . 1 . . C
H10A .5598 .2194 1.1028 .047 Uiso calc R 1 . . H
C11 .4138(4) .2716(3) .9716(2) .0367(7) Uani d . 1 . . C
C12 .4025(4) .2696(3) .8487(2) .0377(7) Uani d . 1 . . C
H12A .3091 .3037 .8151 .045 Uiso calc R 1 . . H
C13 .8413(4) .6396(3) .4478(3) .0378(7) Uani d . 1 . . C
C14 .8896(5) .7863(3) .5130(3) .0554(9) Uani d . 1 . . C
H14A .9396 .8398 .4577 .083 Uiso calc R 1 . . H
H14B .9782 .7937 .5776 .083 Uiso calc R 1 . . H
H14C .7821 .8194 .5454 .083 Uiso calc R 1 . . H
C15 .5973(5) .1436(3) .4073(2) .0441(8) Uani d . 1 . . C
H15A .5435 .0813 .4543 .066 Uiso calc R 1 . . H
H15B .7083 .1158 .3758 .066 Uiso calc R 1 . . H
H15C .5139 .1433 .3416 .066 Uiso calc R 1 . . H
C16 .8184(5) .1018(4) .7429(3) .0549(9) Uani d . 1 . . C
H16A .7949 .1089 .6613 .082 Uiso calc R 1 . . H
H16B .8149 .0075 .7454 .082 Uiso calc R 1 . . H
H16C .9367 .1518 .7720 .082 Uiso calc R 1 . . H
C17 .8266(6) .0905(4) 1.1062(3) .0600(10) Uani d . 1 . . C
H17A .9308 .0492 1.1205 .090 Uiso calc R 1 . . H
H17B .7176 .0341 1.1215 .090 Uiso calc R 1 . . H
H17C .8364 .1792 1.1591 .090 Uiso calc R 1 . . H
C18 .1609(5) .3959(4) 1.0102(3) .0611(10) Uani d . 1 . . C
H18A .0863 .4278 1.0753 .092 Uiso calc R 1 . . H
H18B .0855 .3352 .9454 .092 Uiso calc R 1 . . H
H18C .2223 .4725 .9819 .092 Uiso calc R 1 . . H
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 118.6(2) yes
C9 O5 C17 118.1(2) yes
C11 O6 C18 118.2(2) yes
C2 C1 C6 119.6(2) ?
O2 C2 C1 119.5(2) yes
O2 C2 C3 119.0(2) yes
C1 C2 C3 121.5(2) ?
C2 C3 C4 116.0(3) ?
C2 C3 C13 124.9(3) ?
C4 C3 C13 119.1(2) ?
O4 C4 C5 115.9(2) yes
O4 C4 C3 120.4(3) yes
C5 C4 C3 123.7(2) ?
C4 C5 C6 116.7(3) ?
C4 C5 C15 120.5(2) ?
C6 C5 C15 122.8(3) ?
O1 C6 C1 121.7(2) yes
O1 C6 C5 115.8(2) yes
C1 C6 C5 122.5(3) ?
C12 C7 C8 124.6(2) ?
C12 C7 O1 118.2(3) ?
C8 C7 O1 117.0(3) ?
C7 C8 C9 115.7(3) ?
C7 C8 C16 123.5(3) ?
C9 C8 C16 120.8(3) ?
O5 C9 C10 124.5(3) yes
O5 C9 C8 113.5(3) yes
C10 C9 C8 122.0(3) ?
C9 C10 C11 119.4(3) ?
O6 C11 C12 123.6(3) yes
O6 C11 C10 115.7(2) yes
C12 C11 C10 120.7(3) ?
C7 C12 C11 117.6(3) ?
O3 C13 C3 120.2(3) yes
O3 C13 C14 117.2(3) yes
C3 C13 C14 122.6(3) ?
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 . 1.379(3) yes
O1 C7 . 1.414(3) yes
O2 C2 . 1.366(3) yes
O3 C13 . 1.250(3) yes
O4 C4 . 1.351(3) yes
O5 C9 . 1.373(4) yes
O5 C17 . 1.428(3) yes
O6 C11 . 1.374(3) yes
O6 C18 . 1.432(4) yes
C1 C2 . 1.379(4) ?
C1 C6 . 1.389(4) ?
C2 C3 . 1.417(4) ?
C3 C4 . 1.422(4) ?
C3 C13 . 1.465(4) ?
C4 C5 . 1.391(4) ?
C5 C6 . 1.391(4) ?
C5 C15 . 1.518(4) ?
C7 C12 . 1.373(4) ?
C7 C8 . 1.386(4) ?
C8 C9 . 1.411(4) ?
C8 C16 . 1.505(4) ?
C9 C10 . 1.375(4) ?
C10 C11 . 1.397(4) ?
C11 C12 . 1.393(4) ?
C13 C14 . 1.500(4) ?
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 O6 2_667 .82 2.02 2.837(3) 179 yes
O4 H4A O3 1_555 .82 1.74 2.482(3) 149 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133048
2 PubChem 74765924
