#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/79/2227996.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227996
loop_
_publ_author_name
'Barcon, Alan'
'Brunskill, Andrew P. J.'
'Lalancette, Roger A.'
'Thompson, Hugh W.'
_publ_section_title
;
 4-Oxocyclohexaneacetic acid: catemeric hydrogen bonding and
 spontaneous resolution of a single conformational enantiomer in an
 achiral ε-keto acid
;
_journal_coeditor_code           SJ5037
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2576
_journal_page_last               o2577
_journal_paper_doi               10.1107/S1600536810036652
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H12 O3'
_chemical_formula_moiety         'C8 H12 O3'
_chemical_formula_sum            'C8 H12 O3'
_chemical_formula_weight         156.18
_chemical_melting_point          345
_chemical_name_systematic
;
4-Oxocyclohexaneacetic acid
;
_space_group_IT_number           78
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_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            4
_cell_length_a                   6.8531(12)
_cell_length_b                   6.8531(12)
_cell_length_c                   17.372(3)
_cell_measurement_reflns_used    6759
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.54
_cell_measurement_theta_min      5.09
_cell_volume                     815.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008b)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008b)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_sigmaI/netI    0.017
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6963
_diffrn_reflns_theta_full        70.82
_diffrn_reflns_theta_max         70.82
_diffrn_reflns_theta_min         6.46
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  0.8822
_exptl_absorpt_correction_T_min  0.8063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details 'Flack (1983), 559 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_coef       0.0023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008b)'
_refine_ls_goodness_of_fit_ref   1.18
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1310
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.18
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.039
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0369P)²+0.6710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.108
_refine_ls_wR_factor_ref         0.113
_reflns_number_gt                1274
_reflns_number_total             1310
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5037.cif
_cod_data_source_block           I
_cod_original_cell_volume        815.9(3)
_cod_database_code               2227996
_cod_database_fobs_code          2227996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'
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 0.9958(3) 1.2372(3) 0.08526(13) 0.0341(5) Uani d . 1 . .
O O2 0.2472(4) 0.6544(3) 0.03744(14) 0.0460(6) Uani d . 1 . .
O O3 0.1245(4) 0.5683(4) 0.15016(13) 0.0421(6) Uani d . 1 . .
H H3 0.083(6) 0.482(6) 0.130(2) 0.036(11) Uiso d . 1 . .
C C1 0.4571(4) 0.9768(4) 0.10334(18) 0.0275(6) Uani d . 1 . .
H H1 0.3956 1.0155 0.0534 0.033 Uiso calc R 1 . .
C C2 0.6441(4) 0.8617(4) 0.08592(17) 0.0289(7) Uani d . 1 . .
H H2A 0.7056 0.8208 0.1349 0.035 Uiso calc R 1 . .
H H2B 0.6105 0.7426 0.0565 0.035 Uiso calc R 1 . .
C C3 0.7890(4) 0.9841(4) 0.03955(19) 0.0299(6) Uani d . 1 . .
H H3A 0.9128 0.9109 0.0342 0.036 Uiso calc R 1 . .
H H3B 0.7358 1.0064 -0.0127 0.036 Uiso calc R 1 . .
C C4 0.8297(4) 1.1764(4) 0.07670(18) 0.0294(7) Uani d . 1 . .
C C5 0.6532(5) 1.2912(4) 0.10375(19) 0.0340(7) Uani d . 1 . .
H H5A 0.5867 1.3494 0.0587 0.041 Uiso calc R 1 . .
H H5B 0.6967 1.3990 0.1376 0.041 Uiso calc R 1 . .
C C6 0.5086(4) 1.1616(4) 0.14778(18) 0.0309(7) Uani d . 1 . .
H H6A 0.5662 1.1249 0.1980 0.037 Uiso calc R 1 . .
H H6B 0.3879 1.2365 0.1580 0.037 Uiso calc R 1 . .
C C7 0.3105(4) 0.8534(4) 0.14873(17) 0.0284(6) Uani d . 1 . .
H H7A 0.3757 0.8031 0.1956 0.034 Uiso calc R 1 . .
H H7B 0.2019 0.9386 0.1656 0.034 Uiso calc R 1 . .
C C8 0.2272(4) 0.6841(4) 0.10499(17) 0.0285(7) Uani d . 1 . .
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 0.0344(12) 0.0356(12) 0.0322(12) -0.0107(9) -0.0004(9) 0.0009(9)
O2 0.0644(16) 0.0488(14) 0.0248(12) -0.0289(12) 0.0023(12) -0.0052(10)
O3 0.0544(15) 0.0413(14) 0.0305(12) -0.0195(12) 0.0077(11) -0.0039(11)
C1 0.0327(15) 0.0281(15) 0.0217(14) -0.0034(12) -0.0037(12) 0.0028(12)
C2 0.0366(16) 0.0244(15) 0.0258(16) -0.0003(12) -0.0009(13) -0.0002(12)
C3 0.0321(16) 0.0318(15) 0.0257(15) 0.0002(12) -0.0033(13) 0.0002(13)
C4 0.0353(16) 0.0308(15) 0.0222(14) -0.0054(13) -0.0014(13) 0.0070(12)
C5 0.0407(18) 0.0254(16) 0.0358(18) -0.0041(13) -0.0004(14) -0.0018(13)
C6 0.0282(15) 0.0294(16) 0.0352(17) 0.0007(11) -0.0004(13) -0.0025(14)
C7 0.0311(15) 0.0299(15) 0.0244(15) -0.0004(11) -0.0004(12) 0.0015(12)
C8 0.0270(15) 0.0351(16) 0.0234(16) 0.0001(12) -0.0016(12) 0.0002(12)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C8 O3 H3 . . 114(3) ?
C6 C1 C7 . . 110.5(2) ?
C6 C1 C2 . . 109.5(2) ?
C7 C1 C2 . . 111.4(2) ?
C6 C1 H1 . . 108.5 ?
C7 C1 H1 . . 108.5 ?
C2 C1 H1 . . 108.5 ?
C3 C2 C1 . . 111.4(2) ?
C3 C2 H2A . . 109.4 ?
C1 C2 H2A . . 109.4 ?
C3 C2 H2B . . 109.4 ?
C1 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
C4 C3 C2 . . 112.2(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 ?
O1 C4 C3 . . 121.8(3) ?
O1 C4 C5 . . 121.9(3) ?
C3 C4 C5 . . 116.3(3) ?
C4 C5 C6 . . 111.6(2) ?
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 ?
C1 C6 C5 . . 112.2(2) ?
C1 C6 H6A . . 109.2 ?
C5 C6 H6A . . 109.2 ?
C1 C6 H6B . . 109.2 ?
C5 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
C8 C7 C1 . . 114.6(2) ?
C8 C7 H7A . . 108.6 ?
C1 C7 H7A . . 108.6 ?
C8 C7 H7B . . 108.6 ?
C1 C7 H7B . . 108.6 ?
H7A C7 H7B . . 107.6 ?
O2 C8 O3 . . 122.8(3) ?
O2 C8 C7 . . 125.7(3) ?
O3 C8 C7 . . 111.5(3) ?
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 C4 . 1.222(4) ?
O2 C8 . 1.199(4) ?
O3 C8 . 1.319(4) ?
O3 H3 . 0.74(4) ?
C1 C6 . 1.524(4) ?
C1 C7 . 1.532(4) ?
C1 C2 . 1.535(4) ?
C1 H1 . 1.0000 ?
C2 C3 . 1.529(4) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.494(4) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.518(4) ?
C5 C6 . 1.535(4) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.500(4) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
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
_geom_hbond_publ_flag
O3 H3 O1 1_445 0.75(6) 1.94(6) 2.682(4) 172(6) yes
C7 H7A O2 4_565 0.99 2.51 3.439(5) 156 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -58.4(3) ?
C7 C1 C2 C3 . . . . 179.1(2) ?
C1 C2 C3 C4 . . . . 52.9(3) ?
C2 C3 C4 O1 . . . . 132.3(3) ?
C2 C3 C4 C5 . . . . -47.3(4) ?
O1 C4 C5 C6 . . . . -133.5(3) ?
C3 C4 C5 C6 . . . . 46.0(4) ?
C7 C1 C6 C5 . . . . -179.2(2) ?
C2 C1 C6 C5 . . . . 57.8(3) ?
C4 C5 C6 C1 . . . . -51.0(3) ?
C6 C1 C7 C8 . . . . 171.1(2) ?
C2 C1 C7 C8 . . . . -67.0(3) ?
C1 C7 C8 O2 . . . . -9.6(4) ?
C1 C7 C8 O3 . . . . 171.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8096073
