#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/41/2224187.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_2224187
loop_
_publ_author_name
'Martínez, Roberto'
'Hernández-Ortega, Simón'
'Triana, Liz'
'Camacho, Jose'
_publ_section_title
;
 3-Hydroxy-5,5-dimethyl-2-(2-oxopropyl)cyclohex-2-enone
;
_journal_coeditor_code           DN2511
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3186
_journal_paper_doi               10.1107/S1600536809049046
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H16 O3'
_chemical_formula_moiety         'C11 H16 O3'
_chemical_formula_sum            'C11 H16 O3'
_chemical_formula_weight         196.24
_chemical_melting_point          406
_chemical_name_systematic
;
3-Hydroxy-5,5-dimethyl-2-(2-oxopropyl)cyclohex-2-enone
;
_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                 105.352(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.005(3)
_cell_length_b                   13.633(4)
_cell_length_c                   8.441(2)
_cell_measurement_reflns_used    4286
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.50
_cell_volume                     1110.3(5)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD 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  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8977
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.191
_refine_ls_extinction_coef       0.021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2032
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0704P)²+0.0505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1256
_reflns_number_gt                1573
_reflns_number_total             2032
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2511.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224187
_cod_database_fobs_code          2224187
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 0.96277(13) 0.77843(7) 0.23295(14) 0.0636(4) Uani d . 1 . .
O O2 0.92396(12) 0.44317(7) 0.16061(14) 0.0577(4) Uani d D 1 . .
H H2 0.9653(18) 0.3880(11) 0.199(2) 0.069 Uiso d D 1 . .
O O3 0.68935(15) 0.65312(12) 0.26209(17) 0.0924(5) Uani d . 1 . .
C C1 1.00978(16) 0.69523(9) 0.27353(17) 0.0457(4) Uani d . 1 . .
C C2 0.94081(15) 0.61103(9) 0.18949(17) 0.0431(4) Uani d . 1 . .
C C3 0.99433(15) 0.52082(9) 0.23391(17) 0.0422(4) Uani d . 1 . .
C C4 1.12691(15) 0.50283(10) 0.36178(18) 0.0467(4) Uani d . 1 . .
H H4A 1.1757 0.4495 0.3255 0.056 Uiso calc R 1 . .
H H4B 1.1055 0.4820 0.4622 0.056 Uiso calc R 1 . .
C C5 1.22308(15) 0.59193(10) 0.39985(17) 0.0473(4) Uani d . 1 . .
C C6 1.13588(17) 0.68191(11) 0.41453(18) 0.0529(4) Uani d . 1 . .
H H6A 1.1069 0.6766 0.5151 0.064 Uiso calc R 1 . .
H H6B 1.1935 0.7399 0.4234 0.064 Uiso calc R 1 . .
C C7 0.80924(16) 0.62619(11) 0.05840(18) 0.0510(4) Uani d . 1 . .
H H7A 0.8230 0.6794 -0.0119 0.061 Uiso calc R 1 . .
H H7B 0.7901 0.5674 -0.0085 0.061 Uiso calc R 1 . .
C C8 0.68542(18) 0.64907(12) 0.1183(2) 0.0616(5) Uani d . 1 . .
C C9 0.5541(2) 0.6657(2) -0.0119(3) 0.1196(10) Uani d . 1 . .
H H9A 0.5341 0.6094 -0.0824 0.179 Uiso calc R 1 . .
H H9B 0.5639 0.7224 -0.0754 0.179 Uiso calc R 1 . .
H H9C 0.4796 0.6762 0.0382 0.179 Uiso calc R 1 . .
C C10 1.29416(18) 0.60741(12) 0.26238(19) 0.0609(5) Uani d . 1 . .
H H10A 1.2252 0.6147 0.1596 0.091 Uiso calc R 1 . .
H H10B 1.3516 0.5518 0.2568 0.091 Uiso calc R 1 . .
H H10C 1.3503 0.6655 0.2844 0.091 Uiso calc R 1 . .
C C11 1.33259(19) 0.57556(14) 0.5624(2) 0.0702(5) Uani d . 1 . .
H H11A 1.3837 0.5168 0.5555 0.105 Uiso calc R 1 . .
H H11B 1.2880 0.5691 0.6496 0.105 Uiso calc R 1 . .
H H11C 1.3948 0.6305 0.5844 0.105 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
C3 O2 H2 . . 111.8(12) ?
O1 C1 C2 . . 119.99(14) ?
O1 C1 C6 . . 120.52(13) ?
C2 C1 C6 . . 119.45(12) ?
C3 C2 C1 . . 119.28(13) ?
C3 C2 C7 . . 122.51(12) ?
C1 C2 C7 . . 118.19(12) ?
O2 C3 C2 . . 118.19(13) ?
O2 C3 C4 . . 117.74(12) ?
C2 C3 C4 . . 124.07(12) ?
C3 C4 C5 . . 114.25(11) ?
C3 C4 H4A . . 108.7 ?
C5 C4 H4A . . 108.7 ?
C3 C4 H4B . . 108.7 ?
C5 C4 H4B . . 108.7 ?
H4A C4 H4B . . 107.6 ?
C10 C5 C11 . . 109.57(14) ?
C10 C5 C6 . . 109.94(12) ?
C11 C5 C6 . . 109.45(12) ?
C10 C5 C4 . . 110.09(12) ?
C11 C5 C4 . . 109.51(13) ?
C6 C5 C4 . . 108.26(12) ?
C1 C6 C5 . . 114.28(11) ?
C1 C6 H6A . . 108.7 ?
C5 C6 H6A . . 108.7 ?
C1 C6 H6B . . 108.7 ?
C5 C6 H6B . . 108.7 ?
H6A C6 H6B . . 107.6 ?
C8 C7 C2 . . 115.25(13) ?
C8 C7 H7A . . 108.5 ?
C2 C7 H7A . . 108.5 ?
C8 C7 H7B . . 108.5 ?
C2 C7 H7B . . 108.5 ?
H7A C7 H7B . . 107.5 ?
O3 C8 C7 . . 122.90(16) ?
O3 C8 C9 . . 121.54(17) ?
C7 C8 C9 . . 115.56(16) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C5 C10 H10A . . 109.5 ?
C5 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C5 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C5 C11 H11A . . 109.5 ?
C5 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C5 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 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 C1 . 1.2409(16) ?
O2 C3 . 1.3298(16) ?
O2 H2 . 0.877(14) ?
O3 C8 . 1.2050(19) ?
C1 C2 . 1.4276(19) ?
C1 C6 . 1.499(2) ?
C2 C3 . 1.3541(18) ?
C2 C7 . 1.493(2) ?
C3 C4 . 1.492(2) ?
C4 C5 . 1.530(2) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C10 . 1.528(2) ?
C5 C11 . 1.529(2) ?
C5 C6 . 1.529(2) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.490(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.491(3) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 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 O1 2_745 0.877(14) 1.692(14) 2.5685(16) 176.9(18)
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
O1 C1 C2 C3 . . . . 179.22(13) ?
C6 C1 C2 C3 . . . . -3.0(2) ?
O1 C1 C2 C7 . . . . -2.5(2) ?
C6 C1 C2 C7 . . . . 175.23(13) ?
C1 C2 C3 O2 . . . . 176.08(12) ?
C7 C2 C3 O2 . . . . -2.1(2) ?
C1 C2 C3 C4 . . . . -3.2(2) ?
C7 C2 C3 C4 . . . . 178.68(13) ?
O2 C3 C4 C5 . . . . 161.35(13) ?
C2 C3 C4 C5 . . . . -19.4(2) ?
C3 C4 C5 C10 . . . . -75.82(16) ?
C3 C4 C5 C11 . . . . 163.65(13) ?
C3 C4 C5 C6 . . . . 44.38(16) ?
O1 C1 C6 C5 . . . . -150.70(14) ?
C2 C1 C6 C5 . . . . 31.5(2) ?
C10 C5 C6 C1 . . . . 69.73(17) ?
C11 C5 C6 C1 . . . . -169.88(13) ?
C4 C5 C6 C1 . . . . -50.56(17) ?
C3 C2 C7 C8 . . . . 102.90(17) ?
C1 C2 C7 C8 . . . . -75.28(18) ?
C2 C7 C8 O3 . . . . -1.6(2) ?
C2 C7 C8 C9 . . . . 179.14(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5424768
