#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/01/2200133.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_2200133
loop_
_publ_author_name
'Azim, Abul'
'Errington, William'
'Parmar, Virinder S.'
_publ_section_title
;
 3-Hydroxy-1-(2-hydroxy-3,4-dimethoxyphenyl)-2-methylpropanone
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o266
_journal_page_last               o268
_journal_paper_doi               10.1107/S1600536801003518
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C12 H16 O5'
_chemical_formula_moiety         'C12 H16 O5'
_chemical_formula_sum            'C12 H16 O5'
_chemical_formula_weight         240.25
_chemical_melting_point          343
_chemical_name_systematic
;
3-Hydroxy-1-(2-hydroxy-3,4-dimethoxyphenyl)-2-methylpropanone
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 134.586(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.9568(12)
_cell_length_b                   10.6129(6)
_cell_length_c                   14.7853(9)
_cell_measurement_reflns_used    4598
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.35
_cell_volume                     2342.0(3)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1994a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL/PC (Siemens, 1994b)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full .991
_diffrn_measured_fraction_theta_max .991
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0180
_diffrn_reflns_av_sigmaI/netI    .0228
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6539
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .106
_exptl_absorpt_correction_T_max  .959
_exptl_absorpt_correction_T_min  .949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .4
_refine_diff_density_max         .199
_refine_diff_density_min         -.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          .0492
_refine_ls_R_factor_gt           .0373
_refine_ls_shift/su_max          .000
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0603P)²+0.4432P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1096
_reflns_number_gt                2008
_reflns_number_total             2534
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6050.cif
_cod_data_source_block           I
_cod_original_cell_volume        2342.0(2)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2200133
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 .23471(6) .10151(9) .38188(9) .0397(2) Uani d . 1 . . O
O2 .11909(7) -.04825(11) .42363(10) .0491(3) Uani d . 1 . . O
H2 .1717(16) -.009(2) .489(2) .093(7) Uiso d . 1 . . H
O3 .25689(6) .33737(10) .40202(9) .0387(2) Uani d . 1 . . O
H3 .2690(12) .2572(19) .4132(17) .063(6) Uiso d . 1 . . H
O4 .18555(6) .56909(8) .33589(9) .0394(2) Uani d . 1 . . O
O5 .00860(6) .60420(9) .14341(9) .0415(3) Uani d . 1 . . O
C1 .15183(8) .11280(12) .29649(12) .0319(3) Uani d . 1 . . C
C2 .09563(9) -.00657(12) .23933(12) .0362(3) Uani d . 1 . . C
H2A .0318 .0158 .1885 .043 Uiso calc R 1 . . H
C3 .12836(10) -.09810(13) .34392(13) .0414(3) Uani d . 1 . . C
H3A .0938 -.1775 .3050 .050 Uiso calc R 1 . . H
H3B .1922 -.1181 .3962 .050 Uiso calc R 1 . . H
C4 .10196(12) -.06568(14) .15105(15) .0518(4) Uani d . 1 . . C
H4A .0840 -.0035 .0876 .078 Uiso calc R 1 . . H
H4B .0622 -.1390 .1081 .078 Uiso calc R 1 . . H
H4C .1638 -.0923 .2011 .078 Uiso calc R 1 . . H
C5 .20792(10) .62533(14) .27336(15) .0490(4) Uani d . 1 . . C
H5A .2502 .6946 .3253 .073 Uiso calc R 1 . . H
H5B .1535 .6580 .1905 .073 Uiso calc R 1 . . H
H5C .2355 .5620 .2614 .073 Uiso calc R 1 . . H
C6 -.08524(9) .62789(14) .03954(14) .0458(4) Uani d . 1 . . C
H6A -.0960 .7190 .0288 .069 Uiso calc R 1 . . H
H6B -.1181 .5891 .0571 .069 Uiso calc R 1 . . H
H6C -.1059 .5918 -.0384 .069 Uiso calc R 1 . . H
C1' .11061(8) .23794(12) .25137(11) .0310(3) Uani d . 1 . . C
C2' .16641(8) .34630(12) .30908(11) .0309(3) Uani d . 1 . . C
C3' .12957(8) .46679(12) .27187(11) .0326(3) Uani d . 1 . . C
C4' .03681(9) .48277(12) .17268(12) .0339(3) Uani d . 1 . . C
C5' -.01932(8) .37699(13) .11258(12) .0353(3) Uani d . 1 . . C
H5'A -.0823 .3872 .0446 .042 Uiso calc R 1 . . H
C6' .01772(8) .25802(12) .15302(12) .0337(3) Uani d . 1 . . C
H6'A -.0210 .1870 .1129 .040 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
C3 O2 H2 106.5(14)
C2' O3 H3 105.9(12)
C3' O4 C5 113.16(10)
C4' O5 C6 118.18(11)
O1 C1 C1' 120.43(11)
O1 C1 C2 117.98(11)
C1' C1 C2 121.58(11)
C1 C2 C3 110.27(11)
C1 C2 C4 108.52(11)
C3 C2 C4 110.90(12)
C1 C2 H2A 109.0
C3 C2 H2A 109.0
C4 C2 H2A 109.0
O2 C3 C2 112.20(12)
O2 C3 H3A 109.2
C2 C3 H3A 109.2
O2 C3 H3B 109.2
C2 C3 H3B 109.2
H3A C3 H3B 107.9
C2 C4 H4A 109.5
C2 C4 H4B 109.5
H4A C4 H4B 109.5
C2 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
O4 C5 H5A 109.5
O4 C5 H5B 109.5
H5A C5 H5B 109.5
O4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
O5 C6 H6A 109.5
O5 C6 H6B 109.5
H6A C6 H6B 109.5
O5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C6' C1' C2' 117.20(11)
C6' C1' C1 123.66(11)
C2' C1' C1 119.14(11)
O3 C2' C3' 117.28(11)
O3 C2' C1' 121.92(11)
C3' C2' C1' 120.81(11)
O4 C3' C2' 118.99(11)
O4 C3' C4' 120.80(11)
C2' C3' C4' 120.19(11)
O5 C4' C3' 115.06(11)
O5 C4' C5' 125.09(11)
C3' C4' C5' 119.84(12)
C6' C5' C4' 119.46(12)
C6' C5' H5'A 120.3
C4' C5' H5'A 120.3
C5' C6' C1' 122.45(11)
C5' C6' H6'A 118.8
C1' C6' H6'A 118.8
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 C1 . 1.2436(15) ?
O2 C3 . 1.4239(18) ?
O2 H2 . .91(2) ?
O3 C2' . 1.3545(15) ?
O3 H3 . .87(2) ?
O4 C3' . 1.3755(14) ?
O4 C5 . 1.4280(18) ?
O5 C4' . 1.3558(16) ?
O5 C6 . 1.4314(16) ?
C1 C1' . 1.4649(17) ?
C1 C2 . 1.5194(17) ?
C2 C3 . 1.5219(19) ?
C2 C4 . 1.536(2) ?
C2 H2A . 1.000 ?
C3 H3A . .990 ?
C3 H3B . .990 ?
C4 H4A . .980 ?
C4 H4B . .980 ?
C4 H4C . .980 ?
C5 H5A . .980 ?
C5 H5B . .980 ?
C5 H5C . .980 ?
C6 H6A . .980 ?
C6 H6B . .980 ?
C6 H6C . .980 ?
C1' C6' . 1.4054(17) ?
C1' C2' . 1.4202(17) ?
C2' C3' . 1.3919(18) ?
C3' C4' . 1.3987(17) ?
C4' C5' . 1.4022(18) ?
C5' C6' . 1.3794(18) ?
C5' H5'A . .950 ?
C6' H6'A . .950 ?
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
O3 H3 O1 . .87(2) 1.73(2) 2.5252(13) 150.8(18)
O2 H2 O3 7_556 .91(2) 2.19(3) 3.0004(15) 149(2)
O2 H2 O4 7_556 .91(2) 2.28(2) 3.0025(14) 137(2)
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
O1 C1 C2 C3 46.75(16) ?
C1' C1 C2 C3 -134.59(12) ?
O1 C1 C2 C4 -74.91(15) ?
C1' C1 C2 C4 103.75(14) ?
C1 C2 C3 O2 62.71(14) ?
C4 C2 C3 O2 -177.06(11) ?
O1 C1 C1' C6' 178.20(11) yes
C2 C1 C1' C6' -.43(19) yes
O1 C1 C1' C2' -1.92(18) yes
C2 C1 C1' C2' 179.46(11) yes
C6' C1' C2' O3 -177.99(11) ?
C1 C1' C2' O3 2.12(18) ?
C6' C1' C2' C3' 2.17(18) ?
C1 C1' C2' C3' -177.72(11) ?
C5 O4 C3' C2' 97.59(14) yes
C5 O4 C3' C4' -83.85(15) yes
O3 C2' C3' O4 -4.19(17) ?
C1' C2' C3' O4 175.66(11) ?
O3 C2' C3' C4' 177.24(11) ?
C1' C2' C3' C4' -2.91(18) ?
C6 O5 C4' C3' 177.60(11) yes
C6 O5 C4' C5' -3.00(19) yes
O4 C3' C4' O5 2.37(17) ?
C2' C3' C4' O5 -179.09(11) ?
O4 C3' C4' C5' -177.07(11) ?
C2' C3' C4' C5' 1.47(19) ?
O5 C4' C5' C6' -178.74(12) ?
C3' C4' C5' C6' .64(19) ?
C4' C5' C6' C1' -1.4(2) ?
C2' C1' C6' C5' -.03(19) ?
C1 C1' C6' C5' 179.86(12) ?
