##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-05-17
_journal_date_accepted     2010-05-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      6
_journal_page_first     o1516
_journal_page_last     o1516
_journal_paper_category     QO
_journal_coeditor_code     OM2342
_publ_contact_author_name     'Songwen Xie'
_publ_contact_author_address
;
Department of Natural, Information, and Mathematical Sciences
Indiana University Kokomo
Kokomo, IN 46904 - 9003
USA
;
_publ_contact_author_email     soxie@iuk.edu
_publ_contact_author_fax     '1 765 455 9310'
_publ_contact_author_phone     '1 765 455 9284'
_publ_section_title
;
4-(2-Methoxyphenyl)-2,6-dimethylcyclohex-3-enecarboxylic acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Xie, Songwen'
;
Department of Natural, Information, and Mathematical Sciences
Indiana University Kokomo
Kokomo, IN 46904--9003
USA
;
    'Fowler, Brian P.'
;
Department of Natural, Information, and Mathematical Sciences
Indiana University Kokomo
Kokomo, IN 46904--9003
USA
;
    'Deyo, Sara M.'
;
Department of Natural, Information, and Mathematical Sciences
Indiana University Kokomo
Kokomo, IN 46904--9003
USA
;
    'Pink, Maren'
;
Indiana University Molecular Structure Center
Indiana University
Bloomington, IN 47405--7102
USA
;
data_I
_chemical_name_systematic
;
4-(2-Methoxyphenyl)-2,6-dimethylcyclohex-3-enecarboxylic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H20 O3'
_chemical_formula_sum     'C16 H20 O3'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C16 H20 O3'
_chemical_formula_weight     260.32
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     14.2283(9)
_cell_length_b     7.1202(5)
_cell_length_c     14.9517(10)
_cell_angle_alpha     90.00
_cell_angle_beta     106.069(2)
_cell_angle_gamma     90.00
_cell_volume     1455.55(17)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4026
_cell_measurement_theta_min     2.8
_cell_measurement_theta_max     26.3
_cell_measurement_temperature     150(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.188
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     560
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9801
_exptl_absorpt_correction_T_max     0.9944
_exptl_special_details
;
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII Kappa Duo'
_diffrn_measurement_device     'Bruker APEXII Kappa Duo'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     83.33
_diffrn_reflns_number     11165
_diffrn_reflns_av_R_equivalents     0.0223
_diffrn_reflns_av_sigmaI/netI     0.0219
_diffrn_reflns_theta_min     1.49
_diffrn_reflns_theta_max     26.37
_diffrn_reflns_theta_full     26.37
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors
based on F² are statistically about twice as large as those based on
F, and R- factors based on ALL data will be even larger.
;
_reflns_number_total     2964
_reflns_number_gt     2296
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0633
_refine_ls_R_factor_gt     0.0478
_refine_ls_wR_factor_gt     0.1258
_refine_ls_wR_factor_ref     0.1378
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.039
_refine_ls_number_reflns     2964
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0653P)²+0.6215P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.561
_refine_diff_density_min     -0.343
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SIR2004 (Burla et al.,  2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 0.88885(9) 0.4779(2) 0.00968(10) 0.0602(5) Uani d . 1 . .
    O O2 1.02302(9) 0.3518(2) 0.10376(10) 0.0531(4) Uani d . 1 . .
    H H2O 1.051(2) 0.411(4) 0.0670(18) 0.082(8) Uiso d . 1 . .
    O O3 0.55725(8) -0.14999(17) 0.09567(7) 0.0342(3) Uani d . 1 . .
    C C1 0.76051(16) -0.0149(3) 0.11315(14) 0.0478(5) Uani d . 1 . .
    H H1A 0.7060 -0.0803 0.0683 0.057 Uiso calc R 1 . .
    H H1B 0.8079 -0.1122 0.1446 0.057 Uiso calc R 1 . .
    C C2 0.81042(14) 0.1106(3) 0.05858(12) 0.0418(5) Uani d . 1 . .
    H H2 0.7585 0.1771 0.0100 0.050 Uiso calc R 1 . .
    C C3 0.87036(12) 0.2591(3) 0.12493(12) 0.0366(4) Uani d . 1 . .
    H H3 0.9175 0.1927 0.1775 0.044 Uiso calc R 1 . .
    C C4 0.80346(14) 0.3809(3) 0.16515(13) 0.0409(4) Uani d . 1 . .
    H H4 0.7610 0.4559 0.1129 0.049 Uiso calc R 1 . .
    C C5 0.73751(16) 0.2583(3) 0.20376(14) 0.0479(5) Uani d . 1 . .
    H H5 0.7053 0.3137 0.2450 0.057 Uiso calc R 1 . .
    C C6 0.72161(11) 0.0741(2) 0.18303(11) 0.0300(4) Uani d . 1 . .
    C C7 0.66838(11) -0.0451(2) 0.23497(10) 0.0279(4) Uani d . 1 . .
    C C8 0.69907(12) -0.0459(2) 0.33172(11) 0.0322(4) Uani d . 1 . .
    H H8 0.7515 0.0337 0.3629 0.039 Uiso calc R 1 . .
    C C9 0.65520(14) -0.1596(2) 0.38384(11) 0.0377(4) Uani d . 1 . .
    H H9 0.6772 -0.1570 0.4499 0.045 Uiso calc R 1 . .
    C C10 0.57966(14) -0.2762(3) 0.33929(12) 0.0392(4) Uani d . 1 . .
    H H10 0.5501 -0.3557 0.3748 0.047 Uiso calc R 1 . .
    C C11 0.54636(13) -0.2784(2) 0.24267(12) 0.0343(4) Uani d . 1 . .
    H H11 0.4942 -0.3592 0.2122 0.041 Uiso calc R 1 . .
    C C12 0.58967(11) -0.1624(2) 0.19099(11) 0.0279(4) Uani d . 1 . .
    C C13 0.87078(18) -0.0056(4) 0.00957(17) 0.0680(7) Uani d . 1 . .
    H H13A 0.8984 0.0766 -0.0292 0.102 Uiso calc R 1 . .
    H H13B 0.8290 -0.1004 -0.0297 0.102 Uiso calc R 1 . .
    H H13C 0.9239 -0.0680 0.0560 0.102 Uiso calc R 1 . .
    C C14 0.92794(13) 0.3744(3) 0.07423(12) 0.0409(5) Uani d . 1 . .
    C C15 0.86046(19) 0.5186(3) 0.23835(16) 0.0615(6) Uani d . 1 . .
    H H15A 0.8146 0.5943 0.2615 0.092 Uiso calc R 1 . .
    H H15B 0.8997 0.6013 0.2105 0.092 Uiso calc R 1 . .
    H H15C 0.9037 0.4488 0.2901 0.092 Uiso calc R 1 . .
    C C16 0.47037(14) -0.2506(3) 0.05064(12) 0.0441(5) Uani d . 1 . .
    H H16A 0.4516 -0.2223 -0.0161 0.066 Uiso calc R 1 . .
    H H16B 0.4175 -0.2129 0.0772 0.066 Uiso calc R 1 . .
    H H16C 0.4822 -0.3857 0.0599 0.066 Uiso calc R 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 0.0321(7) 0.0899(12) 0.0542(8) -0.0105(7) 0.0048(6) 0.0408(8)
    O2 0.0299(7) 0.0756(11) 0.0510(8) -0.0106(7) 0.0066(6) 0.0317(7)
    O3 0.0347(6) 0.0422(7) 0.0275(6) -0.0110(5) 0.0115(5) -0.0011(5)
    C1 0.0570(12) 0.0433(11) 0.0542(11) -0.0197(9) 0.0341(10) -0.0117(9)
    C2 0.0365(9) 0.0554(12) 0.0387(9) -0.0140(9) 0.0190(8) -0.0047(8)
    C3 0.0303(9) 0.0444(10) 0.0336(8) -0.0108(8) 0.0066(7) 0.0099(7)
    C4 0.0461(11) 0.0374(10) 0.0397(9) -0.0125(8) 0.0124(8) 0.0025(8)
    C5 0.0604(13) 0.0390(11) 0.0554(11) -0.0104(9) 0.0346(10) -0.0058(9)
    C6 0.0270(8) 0.0360(9) 0.0285(8) -0.0060(7) 0.0100(6) -0.0011(7)
    C7 0.0277(8) 0.0292(8) 0.0294(8) 0.0019(7) 0.0121(6) 0.0008(6)
    C8 0.0318(9) 0.0335(9) 0.0315(8) 0.0020(7) 0.0091(7) -0.0001(7)
    C9 0.0475(10) 0.0398(10) 0.0274(8) 0.0071(8) 0.0129(7) 0.0056(7)
    C10 0.0515(11) 0.0355(9) 0.0374(9) -0.0013(8) 0.0236(8) 0.0088(8)
    C11 0.0382(9) 0.0314(9) 0.0374(9) -0.0046(7) 0.0173(7) 0.0010(7)
    C12 0.0301(8) 0.0279(8) 0.0291(8) 0.0011(7) 0.0138(6) 0.0007(6)
    C13 0.0605(14) 0.0884(18) 0.0704(15) -0.0219(13) 0.0437(12) -0.0283(13)
    C14 0.0299(9) 0.0529(11) 0.0365(9) -0.0122(8) 0.0036(7) 0.0126(8)
    C15 0.0778(16) 0.0467(12) 0.0576(13) -0.0251(12) 0.0148(12) -0.0074(10)
    C16 0.0473(11) 0.0508(11) 0.0334(9) -0.0185(9) 0.0098(8) -0.0066(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell esds are taken into
account individually in the estimation of esds in distances, angles and
torsion angles; correlations between esds in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C14 . 1.219(2) ?
    O2 C14 . 1.312(2) ?
    O2 H2O . 0.88(3) ?
    O3 C12 . 1.3740(19) ?
    O3 C16 . 1.426(2) ?
    C1 C6 . 1.456(2) ?
    C1 C2 . 1.513(2) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 C13 . 1.519(3) ?
    C2 C3 . 1.537(2) ?
    C2 H2 . 1.0000 ?
    C3 C14 . 1.504(2) ?
    C3 C4 . 1.528(3) ?
    C3 H3 . 1.0000 ?
    C4 C5 . 1.508(2) ?
    C4 C15 . 1.525(3) ?
    C4 H4 . 1.0000 ?
    C5 C6 . 1.352(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.491(2) ?
    C7 C8 . 1.391(2) ?
    C7 C12 . 1.406(2) ?
    C8 C9 . 1.386(2) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.376(3) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.390(2) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.387(2) ?
    C11 H11 . 0.9500 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
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
    C14 O2 H2O . . 110.0(18) ?
    C12 O3 C16 . . 117.10(12) ?
    C6 C1 C2 . . 117.26(16) ?
    C6 C1 H1A . . 108.0 ?
    C2 C1 H1A . . 108.0 ?
    C6 C1 H1B . . 108.0 ?
    C2 C1 H1B . . 108.0 ?
    H1A C1 H1B . . 107.2 ?
    C1 C2 C13 . . 110.54(18) ?
    C1 C2 C3 . . 108.53(14) ?
    C13 C2 C3 . . 113.54(16) ?
    C1 C2 H2 . . 108.0 ?
    C13 C2 H2 . . 108.0 ?
    C3 C2 H2 . . 108.0 ?
    C14 C3 C4 . . 111.98(15) ?
    C14 C3 C2 . . 109.42(14) ?
    C4 C3 C2 . . 110.45(14) ?
    C14 C3 H3 . . 108.3 ?
    C4 C3 H3 . . 108.3 ?
    C2 C3 H3 . . 108.3 ?
    C5 C4 C15 . . 111.17(16) ?
    C5 C4 C3 . . 110.10(15) ?
    C15 C4 C3 . . 112.43(17) ?
    C5 C4 H4 . . 107.6 ?
    C15 C4 H4 . . 107.6 ?
    C3 C4 H4 . . 107.6 ?
    C6 C5 C4 . . 123.77(17) ?
    C6 C5 H5 . . 118.1 ?
    C4 C5 H5 . . 118.1 ?
    C5 C6 C1 . . 120.94(16) ?
    C5 C6 C7 . . 120.64(15) ?
    C1 C6 C7 . . 118.33(15) ?
    C8 C7 C12 . . 117.67(14) ?
    C8 C7 C6 . . 119.05(14) ?
    C12 C7 C6 . . 123.25(14) ?
    C9 C8 C7 . . 121.77(16) ?
    C9 C8 H8 . . 119.1 ?
    C7 C8 H8 . . 119.1 ?
    C10 C9 C8 . . 119.56(15) ?
    C10 C9 H9 . . 120.2 ?
    C8 C9 H9 . . 120.2 ?
    C9 C10 C11 . . 120.40(16) ?
    C9 C10 H10 . . 119.8 ?
    C11 C10 H10 . . 119.8 ?
    C12 C11 C10 . . 119.74(16) ?
    C12 C11 H11 . . 120.1 ?
    C10 C11 H11 . . 120.1 ?
    O3 C12 C11 . . 122.89(15) ?
    O3 C12 C7 . . 116.24(13) ?
    C11 C12 C7 . . 120.84(15) ?
    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 ?
    O1 C14 O2 . . 122.86(16) ?
    O1 C14 C3 . . 122.40(16) ?
    O2 C14 C3 . . 114.73(15) ?
    C4 C15 H15A . . 109.5 ?
    C4 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C4 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    O3 C16 H16A . . 109.5 ?
    O3 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    O3 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
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 C13 . . . . 164.10(19) ?
    C6 C1 C2 C3 . . . . 39.0(2) ?
    C1 C2 C3 C14 . . . . 174.85(16) ?
    C13 C2 C3 C14 . . . . 51.5(2) ?
    C1 C2 C3 C4 . . . . -61.4(2) ?
    C13 C2 C3 C4 . . . . 175.22(18) ?
    C14 C3 C4 C5 . . . . 172.34(15) ?
    C2 C3 C4 C5 . . . . 50.1(2) ?
    C14 C3 C4 C15 . . . . -63.1(2) ?
    C2 C3 C4 C15 . . . . 174.67(15) ?
    C15 C4 C5 C6 . . . . -141.8(2) ?
    C3 C4 C5 C6 . . . . -16.6(3) ?
    C4 C5 C6 C1 . . . . -6.3(3) ?
    C4 C5 C6 C7 . . . . 170.29(17) ?
    C2 C1 C6 C5 . . . . -5.8(3) ?
    C2 C1 C6 C7 . . . . 177.46(16) ?
    C5 C6 C7 C8 . . . . -51.6(2) ?
    C1 C6 C7 C8 . . . . 125.06(18) ?
    C5 C6 C7 C12 . . . . 130.28(19) ?
    C1 C6 C7 C12 . . . . -53.0(2) ?
    C12 C7 C8 C9 . . . . 0.9(2) ?
    C6 C7 C8 C9 . . . . -177.28(15) ?
    C7 C8 C9 C10 . . . . 0.4(3) ?
    C8 C9 C10 C11 . . . . -0.9(3) ?
    C9 C10 C11 C12 . . . . 0.0(3) ?
    C16 O3 C12 C11 . . . . 5.2(2) ?
    C16 O3 C12 C7 . . . . -172.68(15) ?
    C10 C11 C12 O3 . . . . -176.46(16) ?
    C10 C11 C12 C7 . . . . 1.4(2) ?
    C8 C7 C12 O3 . . . . 176.16(14) ?
    C6 C7 C12 O3 . . . . -5.7(2) ?
    C8 C7 C12 C11 . . . . -1.8(2) ?
    C6 C7 C12 C11 . . . . 176.29(15) ?
    C4 C3 C14 O1 . . . . -56.8(3) ?
    C2 C3 C14 O1 . . . . 66.0(3) ?
    C4 C3 C14 O2 . . . . 124.50(18) ?
    C2 C3 C14 O2 . . . . -112.68(19) ?
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 H2O O1 3_765 0.88(3) 1.79(3) 2.6640(18) 177(3)
