##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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     SHELXL-97
_journal_date_recd_electronic     2011-09-11
_journal_date_accepted     2011-09-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue     10
_journal_page_first     o2757
_journal_page_last     o2758
_journal_paper_category     QO
_journal_coeditor_code     HG5093
_publ_contact_author_name     'Julio Zukerman-Schpector'
_publ_contact_author_address
;
Department of Chemistry,
Universidade Federal de São Carlos,
13565-905 São Carlos
SP
Brazil
;
_publ_contact_author_email     julio@power.ufscar.br
_publ_contact_author_fax     ' 55 16 3351 8350'
_publ_contact_author_phone     ' 55 16 33518208 '
_publ_section_title
;\
[(2R,3S,6S)-3-Acetyloxy-6-(1-phenyl-1H-1,2,3-\
triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
;
loop_
    _publ_author_name
    _publ_author_address
    'Zukerman-Schpector, Julio'
;
Department of Chemistry,
Universidade Federal de São Carlos,
13565-905 São Carlos
SP
Brazil
;
    'Stefani, Hélio A.'
;
Departamento de Farmácia,
Faculdade de Ciências Farmacêuticas,
Universidade de São Paulo,
São Paulo-SP
Brazil
;
    'Silva, Nathalia C. S.'
;
Departamento de Farmácia,
Faculdade de Ciências Farmacêuticas,
Universidade de São Paulo,
São Paulo-SP
Brazil
;
    'Ng, Seik Weng'
;
Department of Chemistry,
University of Malaya,
50603 Kuala Lumpur,
Malaysia
and
Chemistry Department, Faculty of Science, King Abdulaziz University,
PO Box 80203 Jeddah, Saudi Arabia
;
    'Tiekink, Edward R. T.'
;
Department of Chemistry,
University of Malaya,
50603 Kuala Lumpur,
Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
[(2R,3S,6S)-3-Acetyloxy-6-(1-phenyl-1H-1,2,3-
triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H19 N3 O5'
_chemical_formula_sum     'C18 H19 N3 O5'
_chemical_formula_iupac     'C18 H19 N3 O5'
_chemical_formula_weight     357.36
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     4.79932(7)
_cell_length_b     16.6308(2)
_cell_length_c     10.76331(14)
_cell_angle_alpha     90.00
_cell_angle_beta     93.2250(10)
_cell_angle_gamma     90.00
_cell_volume     857.73(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4088
_cell_measurement_theta_min     2.65
_cell_measurement_theta_max     73.99
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.384
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     376
_exptl_absorpt_coefficient_mu     0.856
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Agilent, 2010)'
_exptl_absorpt_correction_T_min     0.8475
_exptl_absorpt_correction_T_max     0.9585
_exptl_special_details     ?
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
      'Agilent SuperNova Dual Cu at zero diffractometer  with an Atlas detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.4041
_diffrn_reflns_number     5784
_diffrn_reflns_av_R_equivalents     0.0193
_diffrn_reflns_av_sigmaI/netI     0.0275
_diffrn_reflns_theta_min     4.11
_diffrn_reflns_theta_max     74.15
_diffrn_reflns_theta_full     74.15
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     8
_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 >
2σ(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     3369
_reflns_number_gt     3304
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0335
_refine_ls_R_factor_gt     0.0329
_refine_ls_wR_factor_gt     0.0830
_refine_ls_wR_factor_ref     0.0838
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_restrained_S_all     1.042
_refine_ls_number_reflns     3369
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0525P)²+0.1259P] 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     0.140
_refine_diff_density_min     -0.193
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1591 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.09(15)
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'
    'N' 'N' 0.0311 0.0180
                         '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'
_computing_data_collection     'CrysAlis PRO (Agilent, 2010)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2010)'
_computing_structure_solution     'SIR92 (Altomare et al., 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and
MarvinSketch (ChemAxon, 2009)
;
_computing_publication_material     'publCIF (Westrip, 2010)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 -0.1199(2) 0.49978(6) 0.39298(9) 0.0183(2) Uani d . 1 1 . .
    O O2 0.1131(3) 0.41952(8) 0.69075(13) 0.0374(3) Uani d . 1 1 . .
    O O3 0.0424(2) 0.54932(7) 0.63709(10) 0.0230(2) Uani d . 1 1 . .
    O O4 0.0156(3) 0.75452(8) 0.58495(11) 0.0298(3) Uani d . 1 1 . .
    O O5 0.1489(2) 0.70479(7) 0.40355(11) 0.0226(2) Uani d . 1 1 . .
    N N1 0.2553(3) 0.37406(8) 0.10112(11) 0.0163(2) Uani d . 1 1 . .
    N N2 0.2724(3) 0.44506(8) 0.03950(12) 0.0205(3) Uani d . 1 1 . .
    N N3 0.1016(3) 0.49499(8) 0.09098(12) 0.0202(3) Uani d . 1 1 . .
    C C1 0.4329(3) 0.30870(9) 0.07023(15) 0.0174(3) Uani d . 1 1 . .
    C C2 0.5395(4) 0.30667(10) -0.04686(15) 0.0231(3) Uani d . 1 1 . .
    H H2 0.4855 0.3461 -0.1074 0.028 Uiso calc R 1 1 . .
    C C3 0.7260(4) 0.24640(11) -0.07433(16) 0.0274(3) Uani d . 1 1 . .
    H H3 0.8035 0.2451 -0.1536 0.033 Uiso calc R 1 1 . .
    C C4 0.7999(4) 0.18788(10) 0.01356(17) 0.0265(3) Uani d . 1 1 . .
    H H4 0.9275 0.1466 -0.0056 0.032 Uiso calc R 1 1 . .
    C C5 0.6871(4) 0.18983(10) 0.12911(17) 0.0278(4) Uani d . 1 1 . .
    H H5 0.7362 0.1494 0.1888 0.033 Uiso calc R 1 1 . .
    C C6 0.5023(3) 0.25052(10) 0.15854(15) 0.0232(3) Uani d . 1 1 . .
    H H6 0.4251 0.2520 0.2379 0.028 Uiso calc R 1 1 . .
    C C7 0.0740(3) 0.37932(9) 0.19199(13) 0.0177(3) Uani d . 1 1 . .
    H H7 0.0251 0.3385 0.2485 0.021 Uiso calc R 1 1 . .
    C C8 -0.0244(3) 0.45681(9) 0.18467(13) 0.0160(3) Uani d . 1 1 . .
    C C9 -0.2265(3) 0.49831(9) 0.26498(13) 0.0176(3) Uani d . 1 1 . .
    H H9 -0.4020 0.4658 0.2614 0.021 Uiso calc R 1 1 . .
    C C10 -0.3016(3) 0.58149(9) 0.21885(15) 0.0192(3) Uani d . 1 1 . .
    H H10 -0.4012 0.5874 0.1406 0.023 Uiso calc R 1 1 . .
    C C11 -0.2323(3) 0.64660(9) 0.28465(14) 0.0200(3) Uani d . 1 1 . .
    H H11 -0.2926 0.6977 0.2543 0.024 Uiso calc R 1 1 . .
    C C12 -0.0613(3) 0.64194(9) 0.40561(14) 0.0193(3) Uani d . 1 1 . .
    H H12 -0.1821 0.6498 0.4774 0.023 Uiso calc R 1 1 . .
    C C13 0.0863(3) 0.56087(9) 0.41504(14) 0.0181(3) Uani d . 1 1 . .
    H H13 0.2238 0.5577 0.3488 0.022 Uiso calc R 1 1 . .
    C C14 0.2357(3) 0.54349(10) 0.53946(14) 0.0225(3) Uani d . 1 1 . .
    H H14A 0.3170 0.4888 0.5388 0.027 Uiso calc R 1 1 . .
    H H14B 0.3896 0.5825 0.5550 0.027 Uiso calc R 1 1 . .
    C C15 -0.0055(3) 0.48239(10) 0.70412(15) 0.0247(3) Uani d . 1 1 . .
    C C16 -0.2217(4) 0.49774(14) 0.79520(16) 0.0342(4) Uani d . 1 1 . .
    H H16A -0.1650 0.4725 0.8749 0.051 Uiso calc R 1 1 . .
    H H16B -0.4003 0.4750 0.7636 0.051 Uiso calc R 1 1 . .
    H H16C -0.2422 0.5558 0.8070 0.051 Uiso calc R 1 1 . .
    C C17 0.1610(3) 0.75859(9) 0.49755(14) 0.0201(3) Uani d . 1 1 . .
    C C18 0.3763(4) 0.82174(10) 0.47939(18) 0.0270(4) Uani d . 1 1 . .
    H H18A 0.3102 0.8734 0.5100 0.041 Uiso calc R 1 1 . .
    H H18B 0.4096 0.8263 0.3907 0.041 Uiso calc R 1 1 . .
    H H18C 0.5505 0.8069 0.5256 0.041 Uiso calc R 1 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C13 . 1.4289(17) ?
    O1 C9 . 1.4425(17) ?
    O2 C15 . 1.203(2) ?
    O3 C15 . 1.353(2) ?
    O3 C14 . 1.4435(18) ?
    O4 C17 . 1.204(2) ?
    O5 C17 . 1.3494(19) ?
    O5 C12 . 1.4537(18) ?
    N1 C7 . 1.3482(19) ?
    N1 N2 . 1.3591(18) ?
    N1 C1 . 1.4320(19) ?
    N2 N3 . 1.3113(19) ?
    N3 C8 . 1.3617(19) ?
    C1 C6 . 1.384(2) ?
    C1 C2 . 1.387(2) ?
    C2 C3 . 1.387(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.389(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.384(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.392(2) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.373(2) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.503(2) ?
    C9 C10 . 1.507(2) ?
    C9 H9 . 1.0000 ?
    C10 C11 . 1.326(2) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.501(2) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.524(2) ?
    C12 H12 . 1.0000 ?
    C13 C14 . 1.511(2) ?
    C13 H13 . 1.0000 ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 C16 . 1.489(2) ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 C18 . 1.494(2) ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 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
    C13 O1 C9 . . 112.08(11) ?
    C15 O3 C14 . . 117.93(13) ?
    C17 O5 C12 . . 117.77(12) ?
    C7 N1 N2 . . 110.90(12) ?
    C7 N1 C1 . . 129.40(13) ?
    N2 N1 C1 . . 119.55(12) ?
    N3 N2 N1 . . 106.72(12) ?
    N2 N3 C8 . . 109.38(13) ?
    C6 C1 C2 . . 121.36(14) ?
    C6 C1 N1 . . 119.64(14) ?
    C2 C1 N1 . . 118.96(14) ?
    C3 C2 C1 . . 119.13(15) ?
    C3 C2 H2 . . 120.4 ?
    C1 C2 H2 . . 120.4 ?
    C2 C3 C4 . . 120.28(15) ?
    C2 C3 H3 . . 119.9 ?
    C4 C3 H3 . . 119.9 ?
    C5 C4 C3 . . 119.84(15) ?
    C5 C4 H4 . . 120.1 ?
    C3 C4 H4 . . 120.1 ?
    C4 C5 C6 . . 120.51(16) ?
    C4 C5 H5 . . 119.7 ?
    C6 C5 H5 . . 119.7 ?
    C1 C6 C5 . . 118.85(15) ?
    C1 C6 H6 . . 120.6 ?
    C5 C6 H6 . . 120.6 ?
    N1 C7 C8 . . 104.66(13) ?
    N1 C7 H7 . . 127.7 ?
    C8 C7 H7 . . 127.7 ?
    N3 C8 C7 . . 108.34(13) ?
    N3 C8 C9 . . 122.66(13) ?
    C7 C8 C9 . . 128.96(14) ?
    O1 C9 C8 . . 110.58(12) ?
    O1 C9 C10 . . 111.38(12) ?
    C8 C9 C10 . . 112.47(12) ?
    O1 C9 H9 . . 107.4 ?
    C8 C9 H9 . . 107.4 ?
    C10 C9 H9 . . 107.4 ?
    C11 C10 C9 . . 121.71(14) ?
    C11 C10 H10 . . 119.1 ?
    C9 C10 H10 . . 119.1 ?
    C10 C11 C12 . . 121.97(14) ?
    C10 C11 H11 . . 119.0 ?
    C12 C11 H11 . . 119.0 ?
    O5 C12 C11 . . 107.19(12) ?
    O5 C12 C13 . . 108.46(12) ?
    C11 C12 C13 . . 109.44(12) ?
    O5 C12 H12 . . 110.6 ?
    C11 C12 H12 . . 110.6 ?
    C13 C12 H12 . . 110.6 ?
    O1 C13 C14 . . 107.51(12) ?
    O1 C13 C12 . . 107.63(12) ?
    C14 C13 C12 . . 115.09(13) ?
    O1 C13 H13 . . 108.8 ?
    C14 C13 H13 . . 108.8 ?
    C12 C13 H13 . . 108.8 ?
    O3 C14 C13 . . 109.89(12) ?
    O3 C14 H14A . . 109.7 ?
    C13 C14 H14A . . 109.7 ?
    O3 C14 H14B . . 109.7 ?
    C13 C14 H14B . . 109.7 ?
    H14A C14 H14B . . 108.2 ?
    O2 C15 O3 . . 123.73(16) ?
    O2 C15 C16 . . 125.44(17) ?
    O3 C15 C16 . . 110.83(16) ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O4 C17 O5 . . 123.09(14) ?
    O4 C17 C18 . . 125.26(14) ?
    O5 C17 C18 . . 111.64(14) ?
    C17 C18 H18A . . 109.5 ?
    C17 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C17 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 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
    C7 N1 N2 N3 . . . . -0.21(17) ?
    C1 N1 N2 N3 . . . . -176.19(13) ?
    N1 N2 N3 C8 . . . . -0.02(16) ?
    C7 N1 C1 C6 . . . . -21.1(2) ?
    N2 N1 C1 C6 . . . . 154.08(15) ?
    C7 N1 C1 C2 . . . . 161.09(15) ?
    N2 N1 C1 C2 . . . . -23.8(2) ?
    C6 C1 C2 C3 . . . . -2.0(2) ?
    N1 C1 C2 C3 . . . . 175.82(14) ?
    C1 C2 C3 C4 . . . . 1.4(2) ?
    C2 C3 C4 C5 . . . . -0.1(3) ?
    C3 C4 C5 C6 . . . . -0.7(3) ?
    C2 C1 C6 C5 . . . . 1.2(2) ?
    N1 C1 C6 C5 . . . . -176.58(15) ?
    C4 C5 C6 C1 . . . . 0.2(3) ?
    N2 N1 C7 C8 . . . . 0.34(16) ?
    C1 N1 C7 C8 . . . . 175.81(14) ?
    N2 N3 C8 C7 . . . . 0.23(17) ?
    N2 N3 C8 C9 . . . . 178.14(13) ?
    N1 C7 C8 N3 . . . . -0.34(16) ?
    N1 C7 C8 C9 . . . . -178.08(14) ?
    C13 O1 C9 C8 . . . . 78.46(14) ?
    C13 O1 C9 C10 . . . . -47.37(15) ?
    N3 C8 C9 O1 . . . . -117.28(15) ?
    C7 C8 C9 O1 . . . . 60.2(2) ?
    N3 C8 C9 C10 . . . . 7.9(2) ?
    C7 C8 C9 C10 . . . . -174.61(14) ?
    O1 C9 C10 C11 . . . . 9.9(2) ?
    C8 C9 C10 C11 . . . . -114.87(16) ?
    C9 C10 C11 C12 . . . . 3.5(2) ?
    C17 O5 C12 C11 . . . . 124.32(14) ?
    C17 O5 C12 C13 . . . . -117.60(14) ?
    C10 C11 C12 O5 . . . . 135.30(15) ?
    C10 C11 C12 C13 . . . . 17.9(2) ?
    C9 O1 C13 C14 . . . . -165.40(12) ?
    C9 O1 C13 C12 . . . . 70.07(14) ?
    O5 C12 C13 O1 . . . . -169.07(11) ?
    C11 C12 C13 O1 . . . . -52.44(15) ?
    O5 C12 C13 C14 . . . . 71.10(15) ?
    C11 C12 C13 C14 . . . . -172.27(13) ?
    C15 O3 C14 C13 . . . . 117.54(15) ?
    O1 C13 C14 O3 . . . . -63.44(16) ?
    C12 C13 C14 O3 . . . . 56.45(17) ?
    C14 O3 C15 O2 . . . . 3.6(2) ?
    C14 O3 C15 C16 . . . . -176.58(13) ?
    C12 O5 C17 O4 . . . . 3.6(2) ?
    C12 O5 C17 C18 . . . . -177.05(14) ?
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
    C7 H7 O4 2_546 0.95 2.29 3.2207(19) 167
    C9 H9 Cg1 1_455 1.00 2.68 3.5362(16) 144
    C16 H16a N3 1_556 0.98 2.62 3.463(2) 145
    C16 H16b O2 1_455 0.98 2.59 3.570(2) 177
    C18 H18a O1 2_556 0.98 2.54 3.516(2) 174
    C18 H18c O4 1_655 0.98 2.45 3.400(2) 164
