#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/68/2226816.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_2226816
loop_
_publ_author_name
'Najmuldeen, Ibrahim A.'
'Abdul Hadi, Abdul Hamid'
'Awang, Khalijah'
'Mohamad, Khalit'
'Ng, Seik Weng'
_publ_section_title
;
 5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one from Dysoxylum
 macrocarpum (Meliaceae)
;
_journal_coeditor_code           CI5120
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1883
_journal_paper_doi               10.1107/S1600536810025146
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H10 O4'
_chemical_formula_moiety         'C11 H10 O4'
_chemical_formula_sum            'C11 H10 O4'
_chemical_formula_weight         206.19
_chemical_name_systematic
;
5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one
;
_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'
_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                 98.8480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.7393(3)
_cell_length_b                   14.5373(6)
_cell_length_c                   16.8263(7)
_cell_measurement_reflns_used    9622
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.5
_cell_volume                     1870.57(13)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEXII area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17796
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.282
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4285
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0348
_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)+(0.0679P)²+0.4625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                3795
_reflns_number_total             4285
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5120.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226816
_cod_database_fobs_code          2226816
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_type_symbol
_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
O O1 0.49963(9) 0.31112(5) 0.80755(4) 0.01545(16) Uani d . 1 . .
O O2 0.54836(10) 0.03128(5) 0.81510(5) 0.02311(18) Uani d . 1 . .
O O3 0.66721(11) 0.03755(5) 0.67769(5) 0.02290(18) Uani d D 1 . .
O O4 0.71726(10) 0.32572(5) 0.55887(4) 0.01882(17) Uani d . 1 . .
O O5 1.05826(9) 0.38133(5) 0.70570(4) 0.01574(16) Uani d . 1 . .
O O6 1.12544(10) 0.10446(5) 0.73680(5) 0.02192(17) Uani d . 1 . .
O O7 1.00123(11) 0.11679(5) 0.87114(5) 0.02253(18) Uani d D 1 . .
O O8 0.82751(10) 0.40629(5) 0.95136(4) 0.01974(17) Uani d . 1 . .
C C1 0.39489(14) 0.32353(7) 0.93075(6) 0.0200(2) Uani d . 1 . .
H H1A 0.3576 0.2864 0.9737 0.030 Uiso calc R 1 . .
H H1B 0.2964 0.3607 0.9049 0.030 Uiso calc R 1 . .
H H1C 0.4909 0.3641 0.9536 0.030 Uiso calc R 1 . .
C C2 0.45527(12) 0.26180(7) 0.87004(6) 0.0163(2) Uani d . 1 . .
C C3 0.46768(13) 0.16950(7) 0.87405(6) 0.0184(2) Uani d . 1 . .
H H3A 0.4329 0.1383 0.9186 0.022 Uiso calc R 1 . .
C C4 0.53257(12) 0.11694(7) 0.81228(6) 0.0172(2) Uani d . 1 . .
C C5 0.58040(12) 0.17065(6) 0.74648(6) 0.0147(2) Uani d . 1 . .
C C6 0.64722(12) 0.12963(7) 0.68075(6) 0.0160(2) Uani d . 1 . .
C C7 0.69215(12) 0.18335(7) 0.61950(6) 0.0167(2) Uani d . 1 . .
H H7A 0.7379 0.1559 0.5759 0.020 Uiso calc R 1 . .
C C8 0.66943(12) 0.27902(7) 0.62233(6) 0.0148(2) Uani d . 1 . .
C C9 0.60437(12) 0.32217(6) 0.68517(6) 0.01419(19) Uani d . 1 . .
H H9 0.5895 0.3870 0.6864 0.017 Uiso calc R 1 . .
C C10 0.56218(12) 0.26615(6) 0.74610(5) 0.01350(19) Uani d . 1 . .
C C11 0.69519(14) 0.42341(7) 0.55749(6) 0.0205(2) Uani d . 1 . .
H H11A 0.7287 0.4483 0.5079 0.031 Uiso calc R 1 . .
H H11B 0.7693 0.4506 0.6041 0.031 Uiso calc R 1 . .
H H11C 0.5725 0.4383 0.5596 0.031 Uiso calc R 1 . .
C C12 1.16596(14) 0.38672(7) 0.58240(6) 0.0200(2) Uani d . 1 . .
H H12A 1.2153 0.3477 0.5440 0.030 Uiso calc R 1 . .
H H12B 1.2512 0.4340 0.6033 0.030 Uiso calc R 1 . .
H H12C 1.0590 0.4162 0.5553 0.030 Uiso calc R 1 . .
C C13 1.12406(12) 0.32926(7) 0.65014(6) 0.0163(2) Uani d . 1 . .
C C14 1.14769(13) 0.23789(7) 0.65825(6) 0.0180(2) Uani d . 1 . .
H H14 1.1940 0.2047 0.6177 0.022 Uiso calc R 1 . .
C C15 1.10416(12) 0.18917(7) 0.72722(6) 0.0164(2) Uani d . 1 . .
C C16 1.03515(12) 0.24579(6) 0.78581(6) 0.01414(19) Uani d . 1 . .
C C17 0.98490(12) 0.20810(6) 0.85677(6) 0.0159(2) Uani d . 1 . .
C C18 0.91807(12) 0.26380(7) 0.91094(6) 0.0167(2) Uani d . 1 . .
H H18 0.8858 0.2386 0.9586 0.020 Uiso calc R 1 . .
C C19 0.89823(12) 0.35822(7) 0.89482(6) 0.0151(2) Uani d . 1 . .
C C20 0.94688(12) 0.39841(6) 0.82650(6) 0.01472(19) Uani d . 1 . .
H H20 0.9348 0.4626 0.8167 0.018 Uiso calc R 1 . .
C C21 1.01372(12) 0.34029(6) 0.77342(5) 0.01377(19) Uani d . 1 . .
C C22 0.78973(16) 0.50156(7) 0.93552(7) 0.0250(2) Uani d . 1 . .
H H22A 0.7344 0.5275 0.9791 0.038 Uiso calc R 1 . .
H H22B 0.7103 0.5077 0.8845 0.038 Uiso calc R 1 . .
H H22C 0.8986 0.5347 0.9321 0.038 Uiso calc R 1 . .
H H3 0.634(2) 0.0179(12) 0.7204(8) 0.061(6) Uiso d D 1 . .
H H7 1.043(3) 0.0968(13) 0.8304(9) 0.070(6) Uiso d D 1 . .
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
C2 O1 C10 . . 119.45(8) ?
C6 O3 H3 . . 104.5(13) ?
C8 O4 C11 . . 117.45(7) ?
C13 O5 C21 . . 119.70(8) ?
C17 O7 H7 . . 103.2(14) ?
C19 O8 C22 . . 117.32(8) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 O1 . . 122.67(9) ?
C3 C2 C1 . . 126.45(9) ?
O1 C2 C1 . . 110.87(8) ?
C2 C3 C4 . . 121.49(9) ?
C2 C3 H3A . . 119.3 ?
C4 C3 H3A . . 119.3 ?
O2 C4 C3 . . 122.89(9) ?
O2 C4 C5 . . 122.03(9) ?
C3 C4 C5 . . 115.08(9) ?
C10 C5 C6 . . 117.53(8) ?
C10 C5 C4 . . 120.14(9) ?
C6 C5 C4 . . 122.32(9) ?
O3 C6 C7 . . 119.31(9) ?
O3 C6 C5 . . 120.21(9) ?
C7 C6 C5 . . 120.48(9) ?
C6 C7 C8 . . 119.23(9) ?
C6 C7 H7A . . 120.4 ?
C8 C7 H7A . . 120.4 ?
O4 C8 C9 . . 123.04(8) ?
O4 C8 C7 . . 114.59(8) ?
C9 C8 C7 . . 122.37(9) ?
C10 C9 C8 . . 116.85(8) ?
C10 C9 H9 . . 121.6 ?
C8 C9 H9 . . 121.6 ?
O1 C10 C9 . . 115.31(8) ?
O1 C10 C5 . . 121.16(8) ?
C9 C10 C5 . . 123.53(8) ?
O4 C11 H11A . . 109.5 ?
O4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 H12A . . 109.5 ?
C13 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C13 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 O5 . . 122.61(9) ?
C14 C13 C12 . . 126.13(9) ?
O5 C13 C12 . . 111.25(8) ?
C13 C14 C15 . . 121.42(9) ?
C13 C14 H14 . . 119.3 ?
C15 C14 H14 . . 119.3 ?
O6 C15 C14 . . 123.03(9) ?
O6 C15 C16 . . 121.83(9) ?
C14 C15 C16 . . 115.14(9) ?
C21 C16 C17 . . 117.60(8) ?
C21 C16 C15 . . 120.37(9) ?
C17 C16 C15 . . 122.02(9) ?
O7 C17 C18 . . 119.54(9) ?
O7 C17 C16 . . 119.91(9) ?
C18 C17 C16 . . 120.55(9) ?
C17 C18 C19 . . 119.21(9) ?
C17 C18 H18 . . 120.4 ?
C19 C18 H18 . . 120.4 ?
O8 C19 C20 . . 123.40(9) ?
O8 C19 C18 . . 114.27(8) ?
C20 C19 C18 . . 122.33(9) ?
C21 C20 C19 . . 116.84(8) ?
C21 C20 H20 . . 121.6 ?
C19 C20 H20 . . 121.6 ?
O5 C21 C20 . . 115.79(8) ?
O5 C21 C16 . . 120.75(8) ?
C20 C21 C16 . . 123.46(8) ?
O8 C22 H22A . . 109.5 ?
O8 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O8 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 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
O1 C2 . 1.3596(11) ?
O1 C10 . 1.3729(11) ?
O2 C4 . 1.2514(12) ?
O3 C6 . 1.3494(11) ?
O3 H3 . 0.850(9) ?
O4 C8 . 1.3637(11) ?
O4 C11 . 1.4302(12) ?
O5 C13 . 1.3611(11) ?
O5 C21 . 1.3761(11) ?
O6 C15 . 1.2496(12) ?
O7 C17 . 1.3517(11) ?
O7 H7 . 0.852(9) ?
O8 C19 . 1.3612(11) ?
O8 C22 . 1.4319(12) ?
C1 C2 . 1.4880(13) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 C3 . 1.3463(14) ?
C3 C4 . 1.4412(14) ?
C3 H3A . 0.95 ?
C4 C5 . 1.4486(13) ?
C5 C10 . 1.3955(13) ?
C5 C6 . 1.4220(13) ?
C6 C7 . 1.3795(14) ?
C7 C8 . 1.4035(13) ?
C7 H7A . 0.95 ?
C8 C9 . 1.3888(13) ?
C9 C10 . 1.3870(13) ?
C9 H9 . 0.95 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 C13 . 1.4886(13) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C14 . 1.3450(14) ?
C14 C15 . 1.4430(14) ?
C14 H14 . 0.95 ?
C15 C16 . 1.4480(13) ?
C16 C21 . 1.3956(13) ?
C16 C17 . 1.4212(13) ?
C17 C18 . 1.3780(14) ?
C18 C19 . 1.4030(13) ?
C18 H18 . 0.95 ?
C19 C20 . 1.3920(13) ?
C20 C21 . 1.3862(13) ?
C20 H20 . 0.95 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
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
O3 H3 O2 . 0.850(10) 1.830(10) 2.6180(10) 154(2) yes
O7 H7 O6 . 0.850(10) 1.790(10) 2.5950(10) 156(2) yes
C7 H7A O8 4_565 0.95 2.48 3.4222(12) 173 no
C9 H9 O2 2_656 0.95 2.35 3.2614(12) 160 no
C12 H12B O2 2_756 0.98 2.37 3.3326(13) 166 no
C18 H18 O4 4_566 0.95 2.47 3.3904(12) 163 no
C20 H20 O6 2_756 0.95 2.27 3.1995(12) 166 no
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
C10 O1 C2 C3 . . . . -0.95(13) ?
C10 O1 C2 C1 . . . . 178.64(7) ?
O1 C2 C3 C4 . . . . 1.16(15) ?
C1 C2 C3 C4 . . . . -178.35(9) ?
C2 C3 C4 O2 . . . . 178.74(10) ?
C2 C3 C4 C5 . . . . -0.66(14) ?
O2 C4 C5 C10 . . . . -179.40(9) ?
C3 C4 C5 C10 . . . . 0.00(13) ?
O2 C4 C5 C6 . . . . 0.38(15) ?
C3 C4 C5 C6 . . . . 179.78(8) ?
C10 C5 C6 O3 . . . . -179.79(8) ?
C4 C5 C6 O3 . . . . 0.42(14) ?
C10 C5 C6 C7 . . . . 0.16(14) ?
C4 C5 C6 C7 . . . . -179.63(8) ?
O3 C6 C7 C8 . . . . 179.29(9) ?
C5 C6 C7 C8 . . . . -0.66(14) ?
C11 O4 C8 C9 . . . . -1.20(13) ?
C11 O4 C8 C7 . . . . 179.17(8) ?
C6 C7 C8 O4 . . . . -179.82(8) ?
C6 C7 C8 C9 . . . . 0.55(14) ?
O4 C8 C9 C10 . . . . -179.53(8) ?
C7 C8 C9 C10 . . . . 0.08(14) ?
C2 O1 C10 C9 . . . . -179.84(8) ?
C2 O1 C10 C5 . . . . 0.26(13) ?
C8 C9 C10 O1 . . . . 179.48(7) ?
C8 C9 C10 C5 . . . . -0.61(14) ?
C6 C5 C10 O1 . . . . -179.60(8) ?
C4 C5 C10 O1 . . . . 0.19(14) ?
C6 C5 C10 C9 . . . . 0.50(14) ?
C4 C5 C10 C9 . . . . -179.71(9) ?
C21 O5 C13 C14 . . . . 0.18(14) ?
C21 O5 C13 C12 . . . . -179.19(7) ?
O5 C13 C14 C15 . . . . -0.03(15) ?
C12 C13 C14 C15 . . . . 179.24(9) ?
C13 C14 C15 O6 . . . . -179.58(9) ?
C13 C14 C15 C16 . . . . -0.25(14) ?
O6 C15 C16 C21 . . . . 179.72(9) ?
C14 C15 C16 C21 . . . . 0.38(13) ?
O6 C15 C16 C17 . . . . -1.11(15) ?
C14 C15 C16 C17 . . . . 179.55(8) ?
C21 C16 C17 O7 . . . . 179.27(8) ?
C15 C16 C17 O7 . . . . 0.08(14) ?
C21 C16 C17 C18 . . . . -0.18(14) ?
C15 C16 C17 C18 . . . . -179.37(8) ?
O7 C17 C18 C19 . . . . -178.73(9) ?
C16 C17 C18 C19 . . . . 0.72(14) ?
C22 O8 C19 C20 . . . . 5.00(14) ?
C22 O8 C19 C18 . . . . -174.86(9) ?
C17 C18 C19 O8 . . . . 178.59(8) ?
C17 C18 C19 C20 . . . . -1.27(14) ?
O8 C19 C20 C21 . . . . -178.65(8) ?
C18 C19 C20 C21 . . . . 1.19(14) ?
C13 O5 C21 C20 . . . . -179.66(8) ?
C13 O5 C21 C16 . . . . -0.03(13) ?
C19 C20 C21 O5 . . . . 178.99(8) ?
C19 C20 C21 C16 . . . . -0.62(14) ?
C17 C16 C21 O5 . . . . -179.46(8) ?
C15 C16 C21 O5 . . . . -0.26(14) ?
C17 C16 C21 C20 . . . . 0.13(14) ?
C15 C16 C21 C20 . . . . 179.34(9) ?
