#------------------------------------------------------------------------------
#$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/30/2013066.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_2013066
loop_
_publ_author_name
'Newman, Jacob M.'
'Thompson, Hugh W.'
'Lalancette, Roger A.'
_publ_section_title
;
 <i>trans</i>-4-Acetylcyclohexanecarboxylic acid and
 (+-)-<i>trans</i>-2-acetylcyclohexanecarboxylic acid: hydrogen-bonding
 patterns in two isomeric keto acids
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o693
_journal_page_last               o696
_journal_paper_doi               10.1107/S0108270102018553
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C9 H14 O3'
_chemical_formula_moiety         'C9 H14 O3'
_chemical_formula_sum            'C9 H14 O3'
_chemical_formula_weight         170.20
_chemical_melting_point          409
_chemical_name_systematic
;
trans-2-acetylcyclohexanecarboxylic acid
;
_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                 101.47(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.943(2)
_cell_length_b                   10.489(3)
_cell_length_c                   12.778(4)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      10.1
_cell_measurement_theta_min      2.5
_cell_volume                     912.0(5)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP in SHELXL97'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       2\q/\q
_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  0.086
_diffrn_reflns_av_sigmaI/netI    0.098
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3465
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        'variation <3'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.13
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.99
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.99
_refine_ls_R_factor_all          0.107
_refine_ls_R_factor_gt           0.052
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0187P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.088
_refine_ls_wR_factor_ref         0.104
_reflns_number_gt                912
_reflns_number_total             1599
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fr1396.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013066
_cod_database_fobs_code          2013066
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_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
_atom_site_type_symbol
O1 0.4841(3) 1.04319(18) 0.16824(16) 0.0787(7) Uani d . 1 . . O
O2 0.4662(3) 0.90097(16) 0.39422(13) 0.0542(5) Uani d . 1 . . O
O3 0.7196(3) 1.02941(17) 0.45112(13) 0.0630(6) Uani d . 1 . . O
C1 0.7425(3) 0.8925(2) 0.30749(17) 0.0388(6) Uani d . 1 . . C
C2 0.6104(3) 0.8346(2) 0.20943(16) 0.0363(6) Uani d . 1 . . C
C3 0.7354(4) 0.7803(2) 0.13316(19) 0.0499(7) Uani d . 1 . . C
C4 0.8864(4) 0.6840(3) 0.18820(19) 0.0560(8) Uani d . 1 . . C
C5 1.0155(4) 0.7418(3) 0.2861(2) 0.0615(8) Uani d . 1 . . C
C6 0.8939(4) 0.7945(2) 0.36330(19) 0.0514(7) Uani d . 1 . . C
C7 0.4655(4) 0.9301(3) 0.15017(19) 0.0468(7) Uani d . 1 . . C
C8 0.2996(4) 0.8811(3) 0.0659(2) 0.0701(9) Uani d . 1 . . C
C9 0.6285(4) 0.9426(2) 0.38695(17) 0.0389(6) Uani d . 1 . . C
H3 0.6551 1.0465 0.4966 0.095 Uiso calc R 1 . . H
H1 0.8143 0.9638 0.2838 0.047 Uiso calc R 1 . . H
H2A 0.5362 0.7643 0.2330 0.044 Uiso calc R 1 . . H
H3A 0.6498 0.7395 0.0733 0.060 Uiso calc R 1 . . H
H3B 0.8028 0.8497 0.1054 0.060 Uiso calc R 1 . . H
H4A 0.8192 0.6099 0.2089 0.067 Uiso calc R 1 . . H
H4B 0.9674 0.6563 0.1388 0.067 Uiso calc R 1 . . H
H5A 1.0934 0.8100 0.2643 0.074 Uiso calc R 1 . . H
H5B 1.1050 0.6774 0.3220 0.074 Uiso calc R 1 . . H
H6A 0.9803 0.8347 0.4232 0.062 Uiso calc R 1 . . H
H6B 0.8261 0.7250 0.3907 0.062 Uiso calc R 1 . . H
H8A 0.1956 0.9429 0.0532 0.105 Uiso calc PR 0.78(3) . . H
H8B 0.2512 0.8027 0.0896 0.105 Uiso calc PR 0.78(3) . . H
H8C 0.3459 0.8663 0.0010 0.105 Uiso calc PR 0.78(3) . . H
H8D 0.3328 0.7983 0.0426 0.105 Uiso d PR 0.22(3) . . H
H8E 0.2772 0.9386 0.0062 0.105 Uiso d PR 0.22(3) . . H
H8F 0.1826 0.8750 0.0949 0.105 Uiso d PR 0.22(3) . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0997(17) 0.0519(12) 0.0773(14) 0.0197(13) 0.0003(13) -0.0048(11)
O2 0.0496(11) 0.0674(12) 0.0505(11) -0.0157(10) 0.0217(9) -0.0188(9)
O3 0.0650(13) 0.0742(13) 0.0577(11) -0.0243(11) 0.0311(10) -0.0343(10)
C1 0.0459(14) 0.0401(14) 0.0314(12) -0.0083(13) 0.0105(11) -0.0053(11)
C2 0.0389(14) 0.0394(13) 0.0323(12) -0.0013(11) 0.0115(11) -0.0040(11)
C3 0.0527(17) 0.0607(17) 0.0366(13) 0.0016(15) 0.0094(13) -0.0108(13)
C4 0.0604(19) 0.0620(18) 0.0476(14) 0.0111(15) 0.0154(15) -0.0085(13)
C5 0.0489(18) 0.081(2) 0.0543(16) 0.0175(15) 0.0087(15) -0.0085(15)
C6 0.0454(17) 0.0700(19) 0.0367(13) 0.0047(14) 0.0026(13) -0.0089(13)
C7 0.0556(18) 0.0507(17) 0.0379(14) 0.0062(14) 0.0185(14) -0.0009(12)
C8 0.064(2) 0.086(2) 0.0540(17) 0.0047(18) -0.0030(16) 0.0074(16)
C9 0.0464(16) 0.0396(14) 0.0308(12) -0.0041(13) 0.0081(12) -0.0036(11)
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
_geom_angle_publ_flag
C9 C1 C2 112.54(19) ?
C9 C1 C6 108.90(18) ?
C2 C1 C6 110.99(19) ?
C7 C2 C1 112.3(2) ?
C7 C2 C3 109.33(18) ?
C1 C2 C3 110.20(19) ?
C4 C3 C2 112.09(19) ?
C5 C4 C3 110.9(2) ?
C4 C5 C6 111.5(2) ?
C5 C6 C1 110.9(2) ?
O1 C7 C8 120.6(3) ?
O1 C7 C2 121.3(3) ?
C8 C7 C2 118.1(2) ?
O2 C9 O3 122.6(2) ?
O2 C9 C1 122.8(2) y
O3 C9 C1 114.5(2) y
C9 O3 H3 109.5 ?
C9 C1 H1 108.1 ?
C2 C1 H1 108.1 ?
C6 C1 H1 108.1 ?
C7 C2 H2A 108.3 ?
C1 C2 H2A 108.3 ?
C3 C2 H2A 108.3 ?
C4 C3 H3A 109.2 ?
C2 C3 H3A 109.2 ?
C4 C3 H3B 109.2 ?
C2 C3 H3B 109.2 ?
H3A C3 H3B 107.9 ?
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 ?
C4 C5 H5A 109.3 ?
C6 C5 H5A 109.3 ?
C4 C5 H5B 109.3 ?
C6 C5 H5B 109.3 ?
H5A C5 H5B 108.0 ?
C5 C6 H6A 109.5 ?
C1 C6 H6A 109.5 ?
C5 C6 H6B 109.5 ?
C1 C6 H6B 109.5 ?
H6A C6 H6B 108.0 ?
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 ?
C7 C8 H8D 109.5 ?
H8A C8 H8D 141.0 ?
H8B C8 H8D 56.2 ?
H8C C8 H8D 56.3 ?
C7 C8 H8E 109.5 ?
H8A C8 H8E 56.3 ?
H8B C8 H8E 141.0 ?
H8C C8 H8E 56.2 ?
H8D C8 H8E 109.5 ?
C7 C8 H8F 109.4 ?
H8A C8 H8F 56.2 ?
H8B C8 H8F 56.3 ?
H8C C8 H8F 141.1 ?
H8D C8 H8F 109.5 ?
H8E C8 H8F 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 C7 . 1.211(3) ?
O2 C9 . 1.229(3) y
O3 C9 . 1.302(3) y
C1 C9 . 1.501(3) ?
C1 C2 . 1.524(3) ?
C1 C6 . 1.540(3) ?
C2 C7 . 1.512(3) ?
C2 C3 . 1.537(3) ?
C3 C4 . 1.523(3) ?
C4 C5 . 1.513(3) ?
C5 C6 . 1.524(3) ?
C7 C8 . 1.503(4) ?
O3 H3 . 0.8200 ?
C1 H1 . 0.9800 ?
C2 H2A . 0.9800 ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C8 H8D . 0.9602 ?
C8 H8E . 0.9601 ?
C8 H8F . 0.9601 ?
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
C9 C1 C2 C7 60.1(3)
C6 C1 C2 C7 -177.61(18)
C9 C1 C2 C3 -177.8(2)
C6 C1 C2 C3 -55.5(2)
C7 C2 C3 C4 179.4(2)
C1 C2 C3 C4 55.6(3)
C2 C3 C4 C5 -55.5(3)
C3 C4 C5 C6 55.6(3)
C4 C5 C6 C1 -56.2(3)
C9 C1 C6 C5 -179.3(2)
C2 C1 C6 C5 56.3(3)
C1 C2 C7 O1 13.8(3)
C3 C2 C7 O1 -108.8(3)
C1 C2 C7 C8 -167.6(2)
C3 C2 C7 C8 69.8(3)
C2 C1 C9 O2 26.0(3)
C6 C1 C9 O2 -97.5(3)
C2 C1 C9 O3 -157.3(2)
C6 C1 C9 O3 79.2(3)