#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/10/2211009.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_2211009
loop_
_publ_author_name
'M. Periasamy'
'N. Subbulakshmi'
'J. Suresh'
'A. Ponnuswamy'
'S. Natarajan'
_publ_section_title
;
 2-Hydroxy-2-(2-methylphenyl)cyclohexyl acetate
;
_journal_coeditor_code           GG2013
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4966
_journal_page_last               o4968
_journal_paper_doi               10.1107/S1600536806041134
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C15 H20 O3'
_chemical_formula_sum            'C15 H20 O3'
_chemical_formula_weight         248.31
_chemical_name_systematic
;
 Configurational and Conformational assignment in
 1-Acetoxy-2-hydroxy-2-(2-methylphenyl)cyclohexane
;
_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                95.62(2)
_cell_angle_beta                 92.770(10)
_cell_angle_gamma                110.94(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9860(10)
_cell_length_b                   7.656(3)
_cell_length_c                   15.5520(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.6
_cell_volume                     659.8(3)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius MACH3'
_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  0.0131
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2564
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.192
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0408
_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)+(0.0574P)²+0.1816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                1827
_reflns_number_total             2320
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gg2013.cif
_cod_data_source_block           I
_cod_database_code               2211009
_cod_database_fobs_code          2211009
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
O O2 0.3544(2) 0.51464(16) 0.36674(7) 0.0408(3) Uani d . 1
O O1 0.77865(19) 0.70890(16) 0.28992(7) 0.0415(3) Uani d . 1
H H1 0.7813 0.6168 0.3122 0.062 Uiso calc R 1
O O3 -0.0369(2) 0.45550(18) 0.38075(9) 0.0532(4) Uani d . 1
C C2 0.5463(3) 0.6662(2) 0.24562(10) 0.0338(4) Uani d . 1
C C3 0.5628(3) 0.8329(2) 0.19473(10) 0.0380(4) Uani d . 1
H H3A 0.6766 0.8413 0.1515 0.046 Uiso calc R 1
H H3B 0.4072 0.8085 0.1644 0.046 Uiso calc R 1
C C21 0.4748(3) 0.4842(2) 0.18167(10) 0.0341(4) Uani d . 1
C C1 0.3669(3) 0.6639(2) 0.31326(10) 0.0371(4) Uani d . 1
H H1A 0.2081 0.6371 0.2834 0.044 Uiso calc R 1
C C26 0.6302(3) 0.4585(2) 0.12035(10) 0.0377(4) Uani d . 1
C C7 0.1426(3) 0.4251(2) 0.39751(10) 0.0393(4) Uani d . 1
C C22 0.2497(3) 0.3419(2) 0.18048(11) 0.0417(4) Uani d . 1
H H22 0.1445 0.3573 0.2200 0.050 Uiso calc R 1
C C6 0.4412(3) 0.8495(2) 0.37276(12) 0.0491(4) Uani d . 1
H H6A 0.5924 0.8713 0.4058 0.059 Uiso calc R 1
H H6B 0.3210 0.8417 0.4134 0.059 Uiso calc R 1
C C4 0.6405(3) 1.0215(2) 0.25233(12) 0.0470(4) Uani d . 1
H H4A 0.8008 1.0513 0.2799 0.056 Uiso calc R 1
H H4B 0.6452 1.1202 0.2170 0.056 Uiso calc R 1
C C23 0.1774(3) 0.1784(2) 0.12242(12) 0.0512(5) Uani d . 1
H H23 0.0262 0.0861 0.1234 0.061 Uiso calc R 1
C C8 0.1585(4) 0.2818(3) 0.45364(12) 0.0563(5) Uani d . 1
H H8A 0.0012 0.2109 0.4692 0.084 Uiso calc R 1
H H8B 0.2621 0.3442 0.5052 0.084 Uiso calc R 1
H H8C 0.2223 0.1982 0.4226 0.084 Uiso calc R 1
C C25 0.5520(3) 0.2926(3) 0.06249(12) 0.0492(4) Uani d . 1
H H25 0.6537 0.2756 0.0218 0.059 Uiso calc R 1
C C24 0.3301(4) 0.1537(3) 0.06351(12) 0.0547(5) Uani d . 1
H H24 0.2841 0.0441 0.0247 0.066 Uiso calc R 1
C C27 0.8767(3) 0.5992(3) 0.10943(12) 0.0483(4) Uani d . 1
H H27A 0.9829 0.5334 0.0961 0.072 Uiso calc R 1
H H27B 0.9384 0.6831 0.1623 0.072 Uiso calc R 1
H H27C 0.8654 0.6704 0.0630 0.072 Uiso calc R 1
C C5 0.4685(4) 1.0141(2) 0.32095(13) 0.0533(5) Uani d . 1
H H5A 0.3130 1.0003 0.2936 0.064 Uiso calc R 1
H H5B 0.5277 1.1312 0.3598 0.064 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
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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
_geom_angle_publ_flag
C7 O2 C1 117.34(12) ?
C2 O1 H1 109.5 ?
O1 C2 C1 108.76(12) y
O1 C2 C21 110.85(12) y
C1 C2 C21 114.66(13) ?
O1 C2 C3 107.03(12) y
C1 C2 C3 105.89(12) ?
C21 C2 C3 109.27(12) ?
C4 C3 C2 113.27(13) ?
C4 C3 H3A 108.9 ?
C2 C3 H3A 108.9 ?
C4 C3 H3B 108.9 ?
C2 C3 H3B 108.9 ?
H3A C3 H3B 107.7 ?
C22 C21 C26 117.76(15) ?
C22 C21 C2 120.81(14) ?
C26 C21 C2 121.39(14) ?
O2 C1 C6 108.17(13) y
O2 C1 C2 108.23(12) y
C6 C1 C2 112.61(13) ?
O2 C1 H1A 109.3 ?
C6 C1 H1A 109.3 ?
C2 C1 H1A 109.3 ?
C25 C26 C21 118.63(15) ?
C25 C26 C27 115.83(15) y
C21 C26 C27 125.51(15) y
O3 C7 O2 123.94(15) ?
O3 C7 C8 124.54(16) ?
O2 C7 C8 111.52(15) ?
C23 C22 C21 122.31(16) ?
C23 C22 H22 118.8 ?
C21 C22 H22 118.8 ?
C1 C6 C5 111.22(15) ?
C1 C6 H6A 109.4 ?
C5 C6 H6A 109.4 ?
C1 C6 H6B 109.4 ?
C5 C6 H6B 109.4 ?
H6A C6 H6B 108.0 ?
C5 C4 C3 110.58(14) ?
C5 C4 H4A 109.5 ?
C3 C4 H4A 109.5 ?
C5 C4 H4B 109.5 ?
C3 C4 H4B 109.5 ?
H4A C4 H4B 108.1 ?
C24 C23 C22 119.61(17) ?
C24 C23 H23 120.2 ?
C22 C23 H23 120.2 ?
C7 C8 H8A 109.5 ?
C7 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C7 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C24 C25 C26 122.34(17) ?
C24 C25 H25 118.8 ?
C26 C25 H25 118.8 ?
C23 C24 C25 119.34(17) ?
C23 C24 H24 120.3 ?
C25 C24 H24 120.3 ?
C26 C27 H27A 109.5 ?
C26 C27 H27B 109.5 ?
H27A C27 H27B 109.5 ?
C26 C27 H27C 109.5 ?
H27A C27 H27C 109.5 ?
H27B C27 H27C 109.5 ?
C4 C5 C6 110.81(15) ?
C4 C5 H5A 109.5 ?
C6 C5 H5A 109.5 ?
C4 C5 H5B 109.5 ?
C6 C5 H5B 109.5 ?
H5A C5 H5B 108.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C7 1.3448(19) y
O2 C1 1.4611(19) y
O1 C2 1.4331(18) y
O1 H1 0.8200 ?
O3 C7 1.200(2) ?
C2 C1 1.536(2) ?
C2 C21 1.541(2) ?
C2 C3 1.543(2) y
C3 C4 1.526(2) y
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C21 C22 1.395(2) ?
C21 C26 1.412(2) ?
C1 C6 1.524(2) y
C1 H1A 0.9800 ?
C26 C25 1.397(2) ?
C26 C27 1.514(2) ?
C7 C8 1.493(2) ?
C22 C23 1.387(2) ?
C22 H22 0.9300 ?
C6 C5 1.526(3) y
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C4 C5 1.510(3) ?
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C23 C24 1.372(3) ?
C23 H23 0.9300 ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C25 C24 1.375(3) ?
C25 H25 0.9300 ?
C24 H24 0.9300 ?
C27 H27A 0.9600 ?
C27 H27B 0.9600 ?
C27 H27C 0.9600 ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
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
O1 H1 O3 1_655 0.82 2.23 2.9826(19) 154
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
O1 C2 C3 C4 -58.11(17)
C1 C2 C3 C4 57.80(17)
C21 C2 C3 C4 -178.20(13)
O1 C2 C21 C22 131.30(15)
C1 C2 C21 C22 7.7(2)
C3 C2 C21 C22 -110.98(16)
O1 C2 C21 C26 -51.10(18)
C1 C2 C21 C26 -174.71(13)
C3 C2 C21 C26 66.62(17)
C7 O2 C1 C6 90.20(16)
C7 O2 C1 C2 -147.51(13)
O1 C2 C1 O2 -62.15(15)
C21 C2 C1 O2 62.57(16)
C3 C2 C1 O2 -176.88(12)
O1 C2 C1 C6 57.38(17)
C21 C2 C1 C6 -177.90(13)
C3 C2 C1 C6 -57.35(17)
C22 C21 C26 C25 -0.5(2)
C2 C21 C26 C25 -178.15(14)
C22 C21 C26 C27 177.70(15)
C2 C21 C26 C27 0.0(2)
C1 O2 C7 O3 3.1(2)
C1 O2 C7 C8 -177.80(14)
C26 C21 C22 C23 0.7(2)
C2 C21 C22 C23 178.41(15)
O2 C1 C6 C5 177.58(14)
C2 C1 C6 C5 58.02(19)
C2 C3 C4 C5 -58.28(19)
C21 C22 C23 C24 -0.2(3)
C21 C26 C25 C24 -0.3(3)
C27 C26 C25 C24 -178.67(17)
C22 C23 C24 C25 -0.6(3)
C26 C25 C24 C23 0.9(3)
C3 C4 C5 C6 54.4(2)
C1 C6 C5 C4 -54.8(2)
