#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/03/2210303.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_2210303
loop_
_publ_author_name
'Rodríguez-López, Verónica'
'Moreno-Escobar, J. Armando'
'Ávila-Torres, Olga'
'Tlahuext, Hugo'
_publ_section_title
;
 6-Acetyl-5-hydroxy-2,2-dimethyl-2H-chromene
;
_journal_coeditor_code           JH2031
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3616
_journal_page_last               o3617
_journal_paper_doi               10.1107/S1600536806028947
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H14 O3'
_chemical_formula_moiety         'C13 H14 O3'
_chemical_formula_sum            'C13 H14 O3'
_chemical_formula_weight         218.24
_chemical_melting_point          376.6
_chemical_name_common            chromene
_chemical_name_systematic
;
6-Acetyl-5-hydroxy-2,2-dimethyl-2H-chromene
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.269(2)
_cell_length_b                   11.194(2)
_cell_length_c                   19.006(4)
_cell_measurement_reflns_used    129
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.98
_cell_measurement_theta_min      1.94
_cell_volume                     2184.8(7)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL and  publCIF'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10526
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.90
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.172
_refine_ls_abs_structure_details
;
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2038
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.345
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0580
_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)+(0.0256P)²+1.8648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                1867
_reflns_number_total             2038
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2031.cif
_cod_data_source_block           I
_cod_database_code               2210303
_cod_database_fobs_code          2210303
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C C2 0.1620(2) 1.0583(2) 0.20105(12) 0.0195(5) Uani d . 1
C C3 0.2365(2) 1.1174(2) 0.14250(12) 0.0202(5) Uani d . 1
H H3 0.2842 1.1861 0.1520 0.024 Uiso calc R 1
C C4 0.2356(2) 1.0738(2) 0.07768(12) 0.0183(5) Uani d . 1
H H4 0.2858 1.1093 0.0428 0.022 Uiso calc R 1
C C5 0.1554(2) 0.9700(2) 0.06132(12) 0.0164(5) Uani d . 1
C C6 0.1611(2) 0.9079(2) -0.00226(12) 0.0171(5) Uani d . 1
C C7 0.0763(2) 0.8114(2) -0.01597(12) 0.0168(5) Uani d . 1
C C8 -0.0169(2) 0.7822(2) 0.03519(12) 0.0180(5) Uani d . 1
H H8 -0.0741 0.7194 0.0266 0.022 Uiso calc R 1
C C9 -0.0262(2) 0.8434(2) 0.09743(12) 0.0186(5) Uani d . 1
H H9 -0.0901 0.8239 0.1301 0.022 Uiso calc R 1
C C10 0.0616(2) 0.9354(2) 0.11088(12) 0.0163(5) Uani d . 1
C C11 0.0862(2) 0.7453(2) -0.08211(12) 0.0195(5) Uani d . 1
C C12 0.0010(2) 0.6381(2) -0.09461(13) 0.0249(6) Uani d . 1
H H12A 0.0132 0.6100 -0.1419 0.037 Uiso calc R 1
H H12B -0.0886 0.6599 -0.0879 0.037 Uiso calc R 1
H H12C 0.0240 0.5760 -0.0621 0.037 Uiso calc R 1
C C13 0.1039(3) 1.1480(2) 0.25232(13) 0.0247(6) Uani d . 1
H H13A 0.0453 1.2000 0.2276 0.037 Uiso calc R 1
H H13B 0.1724 1.1943 0.2732 0.037 Uiso calc R 1
H H13C 0.0573 1.1062 0.2885 0.037 Uiso calc R 1
C C14 0.2469(3) 0.9672(2) 0.23829(13) 0.0250(6) Uani d . 1
H H14A 0.1966 0.9269 0.2736 0.038 Uiso calc R 1
H H14B 0.3192 1.0069 0.2600 0.038 Uiso calc R 1
H H14C 0.2785 0.9099 0.2048 0.038 Uiso calc R 1
O O1 0.04783(16) 0.99554(14) 0.17225(8) 0.0204(4) Uani d . 1
O O2 0.25131(16) 0.94321(15) -0.04961(9) 0.0210(4) Uani d D 1
H H2 0.2427 0.9046 -0.0860 0.053(11) Uiso calc RD 1
O O3 0.16514(17) 0.77543(16) -0.12821(9) 0.0251(4) Uani 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
O1 C2 C3 109.85(19)
O1 C2 C14 108.03(19)
C3 C2 C14 110.4(2)
O1 C2 C13 103.94(18)
C3 C2 C13 112.6(2)
C14 C2 C13 111.7(2)
C4 C3 C2 121.5(2)
C4 C3 H3 119.2
C2 C3 H3 119.2
C3 C4 C5 119.7(2)
C3 C4 H4 120.1
C5 C4 H4 120.1
C6 C5 C10 118.3(2)
C6 C5 C4 123.9(2)
C10 C5 C4 117.7(2)
O2 C6 C5 117.4(2)
O2 C6 C7 121.6(2)
C5 C6 C7 121.0(2)
C8 C7 C6 118.1(2)
C8 C7 C11 121.7(2)
C6 C7 C11 120.2(2)
C9 C8 C7 122.0(2)
C9 C8 H8 119.0
C7 C8 H8 119.0
C8 C9 C10 118.9(2)
C8 C9 H9 120.6
C10 C9 H9 120.6
O1 C10 C9 117.2(2)
O1 C10 C5 120.9(2)
C9 C10 C5 121.7(2)
O3 C11 C7 121.0(2)
O3 C11 C12 119.0(2)
C7 C11 C12 119.9(2)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C2 C13 H13A 109.5
C2 C13 H13B 109.5
H13A C13 H13B 109.5
C2 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C2 C14 H14A 109.5
C2 C14 H14B 109.5
H14A C14 H14B 109.5
C2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C10 O1 C2 118.31(18)
C6 O2 H2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 O1 1.473(3) yes
C2 C3 1.503(3) yes
C2 C14 1.517(3) ?
C2 C13 1.521(3) ?
C3 C4 1.325(3) yes
C3 H3 0.9300 ?
C4 C5 1.458(3) ?
C4 H4 0.9300 ?
C5 C6 1.395(3) ?
C5 C10 1.402(3) ?
C6 O2 1.350(3) ?
C6 C7 1.412(3) ?
C7 C8 1.403(3) ?
C7 C11 1.462(3) ?
C8 C9 1.370(3) ?
C8 H8 0.9300 ?
C9 C10 1.393(3) ?
C9 H9 0.9300 ?
C10 O1 1.354(3) ?
C11 O3 1.241(3) yes
C11 C12 1.504(3) ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
O2 H2 0.8200 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
O1 C2 C3 C4 -28.5(3) yes
C14 C2 C3 C4 90.5(3) yes
C13 C2 C3 C4 -143.8(2) yes
C2 C3 C4 C5 3.3(3) ?
C3 C4 C5 C6 -170.9(2) ?
C3 C4 C5 C10 13.2(3) ?
C10 C5 C6 O2 179.4(2) ?
C4 C5 C6 O2 3.5(3) ?
C10 C5 C6 C7 -1.1(3) ?
C4 C5 C6 C7 -176.9(2) ?
O2 C6 C7 C8 -178.4(2) ?
C5 C6 C7 C8 2.1(3) ?
O2 C6 C7 C11 1.2(3) ?
C5 C6 C7 C11 -178.3(2) ?
C6 C7 C8 C9 -0.7(3) ?
C11 C7 C8 C9 179.7(2) ?
C7 C8 C9 C10 -1.6(3) ?
C8 C9 C10 O1 178.7(2) ?
C8 C9 C10 C5 2.7(3) ?
C6 C5 C10 O1 -177.2(2) ?
C4 C5 C10 O1 -1.0(3) yes
C6 C5 C10 C9 -1.4(3) ?
C4 C5 C10 C9 174.8(2) ?
C8 C7 C11 O3 176.8(2) ?
C6 C7 C11 O3 -2.8(3) ?
C8 C7 C11 C12 -4.1(3) ?
C6 C7 C11 C12 176.3(2) ?
C9 C10 O1 C2 156.9(2) ?
C5 C10 O1 C2 -27.1(3) ?
C3 C2 O1 C10 40.1(3) ?
C14 C2 O1 C10 -80.4(2) ?
C13 C2 O1 C10 160.78(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 722734
