#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/61/2226130.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_2226130
loop_
_publ_author_name
'Liu, Bingjing'
'Chen, Guangying'
'Cen, Changchun'
'Song, Xinming'
'Han, Changri'
_publ_section_title
;
 1-(5-Hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethan-1-one
;
_journal_coeditor_code           HB5429
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1441
_journal_paper_doi               10.1107/S1600536810018374
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H16 O4'
_chemical_formula_moiety         'C14 H16 O4'
_chemical_formula_sum            'C14 H16 O4'
_chemical_formula_weight         248.28
_chemical_name_common
;
2,2-Dimethyl-5-hydroxy-7-methoxy-6-acetylchromene
;
_chemical_name_systematic
;
1-(5-Hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethan-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.9480(10)
_cell_angle_beta                 77.4110(10)
_cell_angle_gamma                84.465(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3797(9)
_cell_length_b                   8.0066(10)
_cell_length_c                   11.2878(14)
_cell_measurement_reflns_used    1208
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.07
_cell_measurement_theta_min      2.606
_cell_volume                     635.67(14)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3335
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0801P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1591
_reflns_number_gt                1361
_reflns_number_total             2217
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5429.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2226130
_cod_database_fobs_code          2226130
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.1836(2) 0.20248(18) 0.25325(13) 0.0529(5) Uani d . 1 . .
O O2 0.2390(2) 0.76852(19) 0.29434(15) 0.0659(5) Uani d . 1 . .
H H2 0.2508 0.8241 0.3453 0.099 Uiso calc R 1 . .
O O3 0.2742(3) 0.8220(2) 0.49648(17) 0.0720(6) Uani d . 1 . .
O O4 0.2615(2) 0.30717(19) 0.63521(13) 0.0604(5) Uani d . 1 . .
C C1 0.2377(3) 0.2453(3) 0.11859(19) 0.0534(7) Uani d . 1 . .
C C2 0.2004(4) 0.4317(3) 0.0732(2) 0.0584(7) Uani d . 1 . .
H H2A 0.1813 0.4684 -0.0072 0.070 Uiso calc R 1 . .
C C3 0.1938(3) 0.5467(3) 0.1434(2) 0.0546(7) Uani d . 1 . .
H H3 0.1751 0.6624 0.1116 0.066 Uiso calc R 1 . .
C C4 0.2160(3) 0.4900(3) 0.27044(19) 0.0431(6) Uani d . 1 . .
C C5 0.2349(3) 0.6020(3) 0.3466(2) 0.0451(6) Uani d . 1 . .
C C6 0.2498(3) 0.5431(3) 0.47159(19) 0.0419(5) Uani d . 1 . .
C C7 0.2432(3) 0.3632(3) 0.51639(19) 0.0429(6) Uani d . 1 . .
C C8 0.2232(3) 0.2528(3) 0.44272(19) 0.0433(5) Uani d . 1 . .
H H8 0.2184 0.1360 0.4741 0.052 Uiso calc R 1 . .
C C9 0.2101(3) 0.3175(3) 0.32112(19) 0.0411(5) Uani d . 1 . .
C C10 0.1212(4) 0.1353(3) 0.0740(2) 0.0695(8) Uani d . 1 . .
H H10A 0.1443 0.0172 0.1090 0.104 Uiso calc R 1 . .
H H10B 0.1534 0.1517 -0.0146 0.104 Uiso calc R 1 . .
H H10C -0.0081 0.1672 0.0992 0.104 Uiso calc R 1 . .
C C11 0.4434(4) 0.1947(4) 0.0849(2) 0.0791(8) Uani d . 1 . .
H H11A 0.5131 0.2610 0.1191 0.119 Uiso calc R 1 . .
H H11B 0.4831 0.2157 -0.0035 0.119 Uiso calc R 1 . .
H H11C 0.4640 0.0754 0.1176 0.119 Uiso calc R 1 . .
C C12 0.2686(3) 0.6685(3) 0.5448(2) 0.0501(6) Uani d . 1 . .
C C13 0.2816(3) 0.6241(3) 0.6777(2) 0.0598(7) Uani d . 1 . .
H H13A 0.2903 0.7267 0.7070 0.090 Uiso calc R 1 . .
H H13B 0.3900 0.5500 0.6867 0.090 Uiso calc R 1 . .
H H13C 0.1727 0.5670 0.7251 0.090 Uiso calc R 1 . .
C C14 0.2647(4) 0.1275(3) 0.6819(2) 0.0717(8) Uani d . 1 . .
H H14A 0.1481 0.0845 0.6811 0.108 Uiso calc R 1 . .
H H14B 0.2846 0.1051 0.7652 0.108 Uiso calc R 1 . .
H H14C 0.3635 0.0720 0.6310 0.108 Uiso calc R 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
C9 O1 C1 . . 118.89(16) ?
C5 O2 H2 . . 109.5 ?
C7 O4 C14 . . 118.00(17) ?
O1 C1 C2 . . 110.59(18) ?
O1 C1 C10 . . 104.22(17) ?
C2 C1 C10 . . 112.3(2) ?
O1 C1 C11 . . 106.92(19) ?
C2 C1 C11 . . 111.2(2) ?
C10 C1 C11 . . 111.3(2) ?
C3 C2 C1 . . 122.2(2) ?
C3 C2 H2A . . 118.9 ?
C1 C2 H2A . . 118.9 ?
C2 C3 C4 . . 119.3(2) ?
C2 C3 H3 . . 120.3 ?
C4 C3 H3 . . 120.3 ?
C9 C4 C5 . . 117.9(2) ?
C9 C4 C3 . . 118.6(2) ?
C5 C4 C3 . . 123.4(2) ?
O2 C5 C4 . . 116.2(2) ?
O2 C5 C6 . . 121.7(2) ?
C4 C5 C6 . . 122.1(2) ?
C5 C6 C7 . . 116.38(19) ?
C5 C6 C12 . . 118.6(2) ?
C7 C6 C12 . . 125.0(2) ?
O4 C7 C8 . . 121.91(19) ?
O4 C7 C6 . . 116.15(18) ?
C8 C7 C6 . . 121.93(19) ?
C7 C8 C9 . . 119.2(2) ?
C7 C8 H8 . . 120.4 ?
C9 C8 H8 . . 120.4 ?
O1 C9 C4 . . 120.78(18) ?
O1 C9 C8 . . 116.67(18) ?
C4 C9 C8 . . 122.51(19) ?
C1 C10 H10A . . 109.5 ?
C1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C1 C11 H11A . . 109.5 ?
C1 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C1 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O3 C12 C6 . . 119.8(2) ?
O3 C12 C13 . . 116.2(2) ?
C6 C12 C13 . . 124.0(2) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
O4 C14 H14A . . 109.5 ?
O4 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O4 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 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 C9 . 1.367(2) ?
O1 C1 . 1.460(2) ?
O2 C5 . 1.341(2) ?
O2 H2 . 0.8200 ?
O3 C12 . 1.237(3) ?
O4 C7 . 1.354(2) ?
O4 C14 . 1.424(3) ?
C1 C2 . 1.493(3) ?
C1 C10 . 1.513(3) ?
C1 C11 . 1.519(3) ?
C2 C3 . 1.326(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.451(3) ?
C3 H3 . 0.9300 ?
C4 C9 . 1.381(3) ?
C4 C5 . 1.401(3) ?
C5 C6 . 1.415(3) ?
C6 C7 . 1.426(3) ?
C6 C12 . 1.460(3) ?
C7 C8 . 1.371(3) ?
C8 C9 . 1.383(3) ?
C8 H8 . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.490(3) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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
O2 H2 O3 . 0.82 1.75 2.479(2) 147
C8 H8 O3 1_545 0.93 2.48 3.374(3) 162
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
C9 O1 C1 C2 . . . . -36.1(3) ?
C9 O1 C1 C10 . . . . -157.02(19) ?
C9 O1 C1 C11 . . . . 85.1(2) ?
O1 C1 C2 C3 . . . . 25.1(3) ?
C10 C1 C2 C3 . . . . 141.0(2) ?
C11 C1 C2 C3 . . . . -93.6(3) ?
C1 C2 C3 C4 . . . . -2.5(4) ?
C2 C3 C4 C9 . . . . -11.4(3) ?
C2 C3 C4 C5 . . . . 171.5(2) ?
C9 C4 C5 O2 . . . . -179.63(18) ?
C3 C4 C5 O2 . . . . -2.6(3) ?
C9 C4 C5 C6 . . . . 0.7(3) ?
C3 C4 C5 C6 . . . . 177.72(19) ?
O2 C5 C6 C7 . . . . 179.90(18) ?
C4 C5 C6 C7 . . . . -0.4(3) ?
O2 C5 C6 C12 . . . . 0.5(3) ?
C4 C5 C6 C12 . . . . -179.84(19) ?
C14 O4 C7 C8 . . . . 1.7(3) ?
C14 O4 C7 C6 . . . . -177.06(19) ?
C5 C6 C7 O4 . . . . 178.63(19) ?
C12 C6 C7 O4 . . . . -2.0(3) ?
C5 C6 C7 C8 . . . . -0.1(3) ?
C12 C6 C7 C8 . . . . 179.2(2) ?
O4 C7 C8 C9 . . . . -178.26(18) ?
C6 C7 C8 C9 . . . . 0.4(3) ?
C1 O1 C9 C4 . . . . 25.4(3) ?
C1 O1 C9 C8 . . . . -157.02(19) ?
C5 C4 C9 O1 . . . . 177.07(19) ?
C3 C4 C9 O1 . . . . -0.1(3) ?
C5 C4 C9 C8 . . . . -0.4(3) ?
C3 C4 C9 C8 . . . . -177.6(2) ?
C7 C8 C9 O1 . . . . -177.73(18) ?
C7 C8 C9 C4 . . . . -0.2(3) ?
C5 C6 C12 O3 . . . . -1.2(3) ?
C7 C6 C12 O3 . . . . 179.5(2) ?
C5 C6 C12 C13 . . . . 178.7(2) ?
C7 C6 C12 C13 . . . . -0.6(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9303772
