##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL-97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2004-12-23
_journal_date_accepted     2005-01-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      2
_journal_page_first     o275
_journal_page_last     o276
_journal_paper_category     EO
_publ_contact_author_name     'Jin, Long-Fei'
_publ_contact_author_address
;
  College of Chemistry
  Central China Normal Univesity
  Wuhan 430079
  People's Republic of China
;
_publ_contact_author_email     jlf163@public.wh.hb.cn
_publ_contact_author_fax     '86 27 67867985'
_publ_contact_author_phone     '86-27-62812177'
_publ_section_title
;
Ethyl 3-hydroxy-2-naphthoate
;
loop_
    _publ_author_name
    _publ_author_address
    'Jin, Cheng-Zhi'
;
College of Chemistry
Central China Normal Univesity
Wuhan 430079
People's Republic of China
;
    'Jin, Long-Fei'
;
College of Chemistry
Central China Normal Univesity
Wuhan 430079
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl 3-hydroxy-2-naphthoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H12 O3'
_chemical_formula_sum     'C13 H12 O3'
_chemical_formula_iupac     'C13 H12 O3'
_chemical_formula_weight     216.23
_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     13.8103(9)
_cell_length_b     11.5082(7)
_cell_length_c     15.0809(9)
_cell_angle_alpha     90.00
_cell_angle_beta     113.2360(10)
_cell_angle_gamma     90.00
_cell_volume     2202.4(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     1884
_cell_measurement_theta_min     2.30
_cell_measurement_theta_max     20.91
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.304
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     912
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9728
_exptl_absorpt_correction_T_max     0.9908
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     14743
_diffrn_reflns_av_R_equivalents     0.0498
_diffrn_reflns_av_sigmaI/netI     0.0520
_diffrn_reflns_theta_min     2.30
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.979
_diffrn_measured_fraction_theta_full     0.979
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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 > 2sigma(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     4236
_reflns_number_gt     2440
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1210
_refine_ls_R_factor_gt     0.0636
_refine_ls_wR_factor_gt     0.1221
_refine_ls_wR_factor_ref     0.1467
_refine_ls_goodness_of_fit_ref     1.043
_refine_ls_restrained_S_all     1.043
_refine_ls_number_reflns     4236
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
      'calc w = 1/[σ²(Fo²)+(0.0493P)²+0.255P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.181
_refine_diff_density_min     -0.137
_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     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXTL (Bruker, 2001)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
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 0.02023(15) 1.00416(15) 0.27366(13) 0.0609(5) Uani d . 1 . . O
    O2 0.19402(18) 1.0096(2) 0.32032(16) 0.0905(7) Uani d . 1 . . O
    O3 0.27429(16) 0.9539(2) 0.19412(16) 0.0820(7) Uani d . 1 . . O
    H3 0.2749 0.9788 0.2453 0.123 Uiso calc R 1 . . H
    C1 -0.0087(2) 0.8949(2) 0.10586(19) 0.0496(7) Uani d . 1 . . C
    H1 -0.0646 0.9043 0.1249 0.060 Uiso calc R 1 . . H
    C2 0.0900(2) 0.9313(2) 0.1667(2) 0.0502(7) Uani d . 1 . . C
    C3 0.1754(2) 0.9167(2) 0.1378(2) 0.0578(7) Uani d . 1 . . C
    C4 0.1586(3) 0.8671(2) 0.0509(2) 0.0649(8) Uani d . 1 . . C
    H4 0.2152 0.8575 0.0328 0.078 Uiso calc R 1 . . H
    C5 0.0378(3) 0.7795(3) -0.1037(2) 0.0736(9) Uani d . 1 . . C
    H5 0.0928 0.7695 -0.1239 0.088 Uiso calc R 1 . . H
    C6 -0.0599(3) 0.7458(2) -0.1617(2) 0.0792(10) Uani d . 1 . . C
    H6 -0.0713 0.7133 -0.2214 0.095 Uiso calc R 1 . . H
    C7 -0.1451(3) 0.7588(2) -0.1340(2) 0.0730(9) Uani d . 1 . . C
    H7 -0.2122 0.7348 -0.1749 0.088 Uiso calc R 1 . . H
    C8 -0.1288(2) 0.8068(2) -0.0467(2) 0.0604(8) Uani d . 1 . . C
    H8 -0.1852 0.8152 -0.0282 0.072 Uiso calc R 1 . . H
    C9 -0.0280(2) 0.8437(2) 0.0157(2) 0.0498(7) Uani d . 1 . . C
    C10 0.0584(2) 0.8302(2) -0.0120(2) 0.0545(7) Uani d . 1 . . C
    C11 0.1081(2) 0.9847(2) 0.2603(2) 0.0574(7) Uani d . 1 . . C
    C12 0.0328(3) 1.0587(3) 0.3645(2) 0.0799(10) Uani d . 1 . . C
    H12A 0.0690 1.1325 0.3715 0.096 Uiso calc R 1 . . H
    H12B 0.0740 1.0091 0.4182 0.096 Uiso calc R 1 . . H
    C13 -0.0734(3) 1.0766(3) 0.3632(2) 0.0914(11) Uani d . 1 . . C
    H13A -0.1106 1.1327 0.3146 0.137 Uiso calc R 1 . . H
    H13B -0.0676 1.1043 0.4251 0.137 Uiso calc R 1 . . H
    H13C -0.1112 1.0043 0.3491 0.137 Uiso calc R 1 . . H
    O4 0.55695(15) 0.18402(16) 0.39717(15) 0.0704(6) Uani d . 1 . . O
    O5 0.39951(17) 0.12720(19) 0.38742(18) 0.0947(8) Uani d . 1 . . O
    O6 0.26250(15) 0.2862(2) 0.38624(17) 0.0836(7) Uani d . 1 . . O
    H6A 0.2856 0.2203 0.3877 0.125 Uiso calc R 1 . . H
    C14 0.5011(2) 0.4123(2) 0.37518(18) 0.0553(7) Uani d . 1 . . C
    H14 0.5653 0.3893 0.3743 0.066 Uiso calc R 1 . . H
    C15 0.4322(2) 0.3288(2) 0.38103(18) 0.0547(7) Uani d . 1 . . C
    C16 0.3339(2) 0.3647(3) 0.38139(19) 0.0608(8) Uani d . 1 . . C
    C17 0.3093(2) 0.4799(3) 0.3762(2) 0.0685(8) Uani d . 1 . . C
    H17 0.2446 0.5021 0.3763 0.082 Uiso calc R 1 . . H
    C18 0.3554(3) 0.6861(3) 0.3667(2) 0.0810(10) Uani d . 1 . . C
    H18 0.2915 0.7106 0.3673 0.097 Uiso calc R 1 . . H
    C19 0.4255(3) 0.7659(3) 0.3621(2) 0.0904(11) Uani d . 1 . . C
    H19 0.4088 0.8445 0.3597 0.109 Uiso calc R 1 . . H
    C20 0.5220(3) 0.7326(3) 0.3611(2) 0.0832(10) Uani d . 1 . . C
    H20 0.5689 0.7885 0.3575 0.100 Uiso calc R 1 . . H
    C21 0.5475(2) 0.6172(3) 0.3654(2) 0.0714(9) Uani d . 1 . . C
    H21 0.6121 0.5950 0.3650 0.086 Uiso calc R 1 . . H
    C22 0.4767(2) 0.5316(2) 0.37047(18) 0.0558(7) Uani d . 1 . . C
    C23 0.3783(2) 0.5657(3) 0.37069(19) 0.0616(8) Uani d . 1 . . C
    C24 0.4594(2) 0.2051(3) 0.3883(2) 0.0651(8) Uani d . 1 . . C
    C25 0.5885(3) 0.0627(3) 0.4053(3) 0.0937(11) Uani d . 1 . . C
    H25A 0.5842 0.0285 0.4624 0.112 Uiso calc R 1 . . H
    H25B 0.5422 0.0198 0.3492 0.112 Uiso calc R 1 . . H
    C26 0.6959(3) 0.0579(3) 0.4118(3) 0.1104(13) Uani d . 1 . . C
    H26A 0.6999 0.0953 0.3565 0.166 Uiso calc R 1 . . H
    H26B 0.7173 -0.0217 0.4139 0.166 Uiso calc R 1 . . H
    H26C 0.7415 0.0970 0.4694 0.166 Uiso calc R 1 . . H
_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
    C9 C8 . 1.403(3) ?
    C9 C1 . 1.407(3) ?
    C9 C10 . 1.421(3) ?
    C8 C7 . 1.361(4) ?
    C8 H8 . 0.93 ?
    C7 C6 . 1.404(4) ?
    C7 H7 . 0.93 ?
    C6 C5 . 1.342(4) ?
    C6 H6 . 0.93 ?
    C5 C10 . 1.423(4) ?
    C5 H5 . 0.93 ?
    C10 C4 . 1.399(4) ?
    C4 C3 . 1.363(4) ?
    C4 H4 . 0.93 ?
    C3 O3 . 1.361(3) yes
    C3 C2 . 1.420(4) ?
    C2 C1 . 1.375(3) ?
    C2 C11 . 1.468(4) yes
    C1 H1 . 0.93 ?
    C11 O2 . 1.209(3) ?
    C11 O1 . 1.325(3) yes
    C12 O1 . 1.453(3) yes
    C12 C13 . 1.474(4) ?
    C12 H12A . 0.97 ?
    C12 H12B . 0.97 ?
    C13 H13A . 0.96 ?
    C13 H13B . 0.96 ?
    C13 H13C . 0.96 ?
    C23 C17 . 1.397(4) ?
    C23 C22 . 1.416(4) ?
    C23 C18 . 1.417(4) ?
    C18 C19 . 1.356(4) ?
    C18 H18 . 0.93 ?
    C19 C20 . 1.393(4) ?
    C19 H19 . 0.93 ?
    C22 C14 . 1.408(4) ?
    C22 C21 . 1.411(4) ?
    C21 C20 . 1.369(4) ?
    C21 H21 . 0.93 ?
    C20 H20 . 0.93 ?
    C14 C15 . 1.380(3) ?
    C14 H14 . 0.93 ?
    C15 C16 . 1.421(4) ?
    C15 C24 . 1.465(4) yes
    C16 O6 . 1.361(3) yes
    C16 C17 . 1.363(4) ?
    C17 H17 . 0.93 ?
    C24 O5 . 1.217(3) ?
    C24 O4 . 1.322(3) yes
    C25 C26 . 1.448(4) ?
    C25 O4 . 1.453(3) yes
    C25 H25A . 0.97 ?
    C25 H25B . 0.97 ?
    C26 H26A . 0.96 ?
    C26 H26B . 0.96 ?
    C26 H26C . 0.96 ?
    O3 H3 . 0.82 ?
    O6 H6A . 0.82 ?
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 C9 C1 . . 122.3(2) ?
    C8 C9 C10 . . 119.7(3) ?
    C1 C9 C10 . . 118.0(3) ?
    C7 C8 C9 . . 120.9(3) ?
    C7 C8 H8 . . 119.6 ?
    C9 C8 H8 . . 119.6 ?
    C8 C7 C6 . . 119.5(3) ?
    C8 C7 H7 . . 120.3 ?
    C6 C7 H7 . . 120.3 ?
    C5 C6 C7 . . 121.4(3) ?
    C5 C6 H6 . . 119.3 ?
    C7 C6 H6 . . 119.3 ?
    C6 C5 C10 . . 121.1(3) ?
    C6 C5 H5 . . 119.5 ?
    C10 C5 H5 . . 119.5 ?
    C4 C10 C9 . . 119.2(3) ?
    C4 C10 C5 . . 123.3(3) ?
    C9 C10 C5 . . 117.5(3) ?
    C3 C4 C10 . . 121.8(3) ?
    C3 C4 H4 . . 119.1 ?
    C10 C4 H4 . . 119.1 ?
    O3 C3 C4 . . 118.7(3) ?
    O3 C3 C2 . . 121.4(3) yes
    C4 C3 C2 . . 119.8(3) ?
    C1 C2 C3 . . 119.0(3) ?
    C1 C2 C11 . . 121.1(2) ?
    C3 C2 C11 . . 119.9(3) ?
    C2 C1 C9 . . 122.2(2) ?
    C2 C1 H1 . . 118.9 ?
    C9 C1 H1 . . 118.9 ?
    O2 C11 O1 . . 122.3(3) yes
    O2 C11 C2 . . 124.3(3) yes
    O1 C11 C2 . . 113.5(3) ?
    O1 C12 C13 . . 107.4(3) ?
    O1 C12 H12A . . 110.2 ?
    C13 C12 H12A . . 110.2 ?
    O1 C12 H12B . . 110.2 ?
    C13 C12 H12B . . 110.2 ?
    H12A C12 H12B . . 108.5 ?
    C12 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C12 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C17 C23 C22 . . 118.8(3) ?
    C17 C23 C18 . . 123.2(3) ?
    C22 C23 C18 . . 118.0(3) ?
    C19 C18 C23 . . 120.8(3) ?
    C19 C18 H18 . . 119.6 ?
    C23 C18 H18 . . 119.6 ?
    C18 C19 C20 . . 121.3(3) ?
    C18 C19 H19 . . 119.3 ?
    C20 C19 H19 . . 119.3 ?
    C14 C22 C21 . . 121.7(3) ?
    C14 C22 C23 . . 118.7(3) ?
    C21 C22 C23 . . 119.6(3) ?
    C20 C21 C22 . . 120.6(3) ?
    C20 C21 H21 . . 119.7 ?
    C22 C21 H21 . . 119.7 ?
    C21 C20 C19 . . 119.7(3) ?
    C21 C20 H20 . . 120.1 ?
    C19 C20 H20 . . 120.1 ?
    C15 C14 C22 . . 121.7(3) ?
    C15 C14 H14 . . 119.2 ?
    C22 C14 H14 . . 119.2 ?
    C14 C15 C16 . . 118.8(3) ?
    C14 C15 C24 . . 121.2(3) ?
    C16 C15 C24 . . 120.0(3) ?
    O6 C16 C17 . . 118.6(3) ?
    O6 C16 C15 . . 121.4(3) yes
    C17 C16 C15 . . 120.0(3) ?
    C16 C17 C23 . . 122.0(3) ?
    C16 C17 H17 . . 119.0 ?
    C23 C17 H17 . . 119.0 ?
    O5 C24 O4 . . 121.8(3) yes
    O5 C24 C15 . . 124.2(3) yes
    O4 C24 C15 . . 114.0(3) ?
    C26 C25 O4 . . 107.9(3) ?
    C26 C25 H25A . . 110.1 ?
    O4 C25 H25A . . 110.1 ?
    C26 C25 H25B . . 110.1 ?
    O4 C25 H25B . . 110.1 ?
    H25A C25 H25B . . 108.4 ?
    C25 C26 H26A . . 109.5 ?
    C25 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    C25 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C3 O3 H3 . . 109.5 ?
    C11 O1 C12 . . 116.1(2) ?
    C16 O6 H6A . . 109.5 ?
    C24 O4 C25 . . 116.4(2) ?
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
    C1 C9 C8 C7 . . . . 179.2(2) ?
    C10 C9 C8 C7 . . . . -0.5(4) ?
    C9 C8 C7 C6 . . . . 0.2(4) ?
    C8 C7 C6 C5 . . . . 0.2(5) ?
    C7 C6 C5 C10 . . . . -0.3(5) ?
    C8 C9 C10 C4 . . . . -179.9(2) ?
    C1 C9 C10 C4 . . . . 0.4(3) ?
    C8 C9 C10 C5 . . . . 0.4(3) ?
    C1 C9 C10 C5 . . . . -179.4(2) ?
    C6 C5 C10 C4 . . . . -179.7(3) ?
    C6 C5 C10 C9 . . . . 0.0(4) ?
    C9 C10 C4 C3 . . . . -0.6(4) ?
    C5 C10 C4 C3 . . . . 179.1(3) ?
    C10 C4 C3 O3 . . . . -178.0(2) ?
    C10 C4 C3 C2 . . . . 0.5(4) ?
    O3 C3 C2 C1 . . . . 178.4(2) ?
    C4 C3 C2 C1 . . . . -0.1(4) ?
    O3 C3 C2 C11 . . . . -1.6(4) ?
    C4 C3 C2 C11 . . . . 179.9(2) ?
    C3 C2 C1 C9 . . . . -0.1(4) ?
    C11 C2 C1 C9 . . . . 179.9(2) ?
    C8 C9 C1 C2 . . . . -179.8(2) ?
    C10 C9 C1 C2 . . . . 0.0(4) ?
    C1 C2 C11 O2 . . . . 173.5(3) ?
    C3 C2 C11 O2 . . . . -6.5(4) y
    C1 C2 C11 O1 . . . . -6.7(3) y
    C3 C2 C11 O1 . . . . 173.3(2) ?
    C17 C23 C18 C19 . . . . 179.5(3) ?
    C22 C23 C18 C19 . . . . 0.5(4) ?
    C23 C18 C19 C20 . . . . 0.1(5) ?
    C17 C23 C22 C14 . . . . 0.4(4) ?
    C18 C23 C22 C14 . . . . 179.5(2) ?
    C17 C23 C22 C21 . . . . -179.7(3) ?
    C18 C23 C22 C21 . . . . -0.6(4) ?
    C14 C22 C21 C20 . . . . -179.8(3) ?
    C23 C22 C21 C20 . . . . 0.3(4) ?
    C22 C21 C20 C19 . . . . 0.3(5) ?
    C18 C19 C20 C21 . . . . -0.4(5) ?
    C21 C22 C14 C15 . . . . 179.4(3) ?
    C23 C22 C14 C15 . . . . -0.7(4) ?
    C22 C14 C15 C16 . . . . 0.6(4) ?
    C22 C14 C15 C24 . . . . -178.5(2) ?
    C14 C15 C16 O6 . . . . 179.5(2) ?
    C24 C15 C16 O6 . . . . -1.5(4) ?
    C14 C15 C16 C17 . . . . -0.1(4) ?
    C24 C15 C16 C17 . . . . 179.0(3) ?
    O6 C16 C17 C23 . . . . -179.8(3) ?
    C15 C16 C17 C23 . . . . -0.2(4) ?
    C22 C23 C17 C16 . . . . 0.0(4) ?
    C18 C23 C17 C16 . . . . -179.0(3) ?
    C14 C15 C24 O5 . . . . -175.1(3) ?
    C16 C15 C24 O5 . . . . 5.9(4) y
    C14 C15 C24 O4 . . . . 5.7(4) y
    C16 C15 C24 O4 . . . . -173.4(2) ?
    O2 C11 O1 C12 . . . . 0.7(4) y
    C2 C11 O1 C12 . . . . -179.1(2) ?
    C13 C12 O1 C11 . . . . 177.8(2) y
    O5 C24 O4 C25 . . . . 0.4(4) y
    C15 C24 O4 C25 . . . . 179.6(2) ?
    C26 C25 O4 C24 . . . . 178.5(3) y
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 O2 . 0.82 1.91 2.632(3) 146 yes
    O6 H6A O5 . 0.82 1.90 2.627(3) 146 yes
