##############################################################################
#                                                                            #
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1438541'
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2015-11-15
_journal_date_accepted     2015-11-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue     12
_journal_page_first     1542
_journal_page_last     1544
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989015022434
_journal_coeditor_code     SU5245
_publ_contact_author_name     'Maris Turks'
_publ_contact_author_address
;
Faculty of Material Science and Applied Chemistry, Riga Technical University,
14/24 Azenes street
Riga
LV-1007
Latvia
;
_publ_contact_author_email     'd_stepanovs@osi.lv, maris_turks@ktf.rtu.lv'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
Crystal structure of
3-O-benzyl-4(R)-C-(1-benzyl-1H-1,2,3-triazol-4-\
yl)-1,2-O-isopropylidene-α-D-erythrofuranose
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Semjonovs, Nikita' .
;
Institute of Technology of Organic Chemistry,
Faculty of Materials Science and Applied Chemistry,
Riga Technical University, P. Valdena 3/7, Riga, LV-1048,
Latvia
;
    'Rjabovs, Vitalijs' .
;
Institute of Technology of Organic Chemistry,
Faculty of Materials Science and Applied Chemistry,
Riga Technical University, P. Valdena 3/7, Riga, LV-1048,
Latvia
;
    'Stepanovs, Dmitrijs' .
;
Latvian Institute of Organic Synthesis, Str. Aizkraukles 21, Riga, LV 1006,
Latvia
;
    'Turks, Maris' .
;
Institute of Technology of Organic Chemistry,
Faculty of Materials Science and Applied Chemistry,
Riga Technical University, P. Valdena 3/7, Riga, LV-1048,
Latvia
;
_publ_section_synopsis
;
The title compound is a substituted
2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole. The furanose ring adopts
an envelope conformation, close to C₃-exo, as does the fused
dioxolane ring. In the crystal, molecules are linked by weak C---H...O
hydrogen bonds, forming zigzag chains along [010].
;
_chemical_name_systematic
;\
3-O-Benzyl-4(R)-C-(1-benzyl-1H-1,2,3-triazol-4-\
yl)-1,2-O-isopropylidene-α-D-erythrofuranose
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H25 N3 O4'
_chemical_formula_sum     'C23 H25 N3 O4'
_chemical_formula_iupac     'C23 H25 N3 O4'
_chemical_formula_weight     407.46
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     9.5276(2)
_cell_length_b     10.0030(2)
_cell_length_c     21.9495(7)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2091.89(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     11742
_cell_measurement_theta_min     0.998
_cell_measurement_theta_max     30.034
_cell_measurement_temperature     173(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.17
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.294
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     864
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details     ?
_diffrn_ambient_temperature     173(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     'Nonius KappaCCD'
_diffrn_measurement_method     'φ and ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5878
_diffrn_reflns_av_R_equivalents     0.0703
_diffrn_reflns_av_sigmaI/netI     0.0920
_diffrn_reflns_theta_min     2.24
_diffrn_reflns_theta_max     30.05
_diffrn_reflns_theta_full     30.05
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     30
_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     3423
_reflns_number_gt     1983
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1217
_refine_ls_R_factor_gt     0.0534
_refine_ls_wR_factor_gt     0.0887
_refine_ls_wR_factor_ref     0.1060
_refine_ls_goodness_of_fit_ref     1.021
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     3423
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0425P)²+0.0000P] 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     0.189
_refine_diff_density_min     -0.199
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'none; Friedel pairs merged'
_refine_ls_abs_structure_Flack     ?
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'
    'N' 'N' 0.0061 0.0033
                         '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
;
KappaCCD Server Software (Nonius, 1997)
;
_computing_cell_refinement
;
SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_structure_solution
;
SIR2011 (Burla et al.,  2012)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and
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 1.16295(19) 0.88874(17) 0.19794(8) 0.0303(4) Uani d . 1 1 . .
    C C1 1.2698(3) 0.9325(2) 0.23846(11) 0.0257(6) Uani d . 1 1 . .
    H H1 1.2802 1.0299 0.2367 0.031 Uiso calc R 1 1 . .
    C C2 1.2262(3) 0.8879(2) 0.30203(12) 0.0264(6) Uani d . 1 1 . .
    H H2 1.2484 0.9535 0.3338 0.032 Uiso calc R 1 1 . .
    C C3 1.0704(3) 0.8622(2) 0.29521(11) 0.0249(6) Uani d . 1 1 . .
    H H3 1.0190 0.9468 0.2983 0.030 Uiso calc R 1 1 . .
    C C4 1.0612(3) 0.8090(2) 0.23003(11) 0.0255(6) Uani d . 1 1 . .
    H H4 1.0914 0.7153 0.2295 0.031 Uiso calc R 1 1 . .
    C C5 0.9254(3) 0.8207(2) 0.19804(11) 0.0247(6) Uani d . 1 1 . .
    C C6 0.8620(3) 0.9299(3) 0.17250(11) 0.0281(7) Uani d . 1 1 . .
    H H6 0.8943 1.0176 0.1724 0.034 Uiso calc R 1 1 . .
    N N7 0.8440(3) 0.7120(2) 0.18755(10) 0.0330(6) Uani d . 1 1 . .
    N N8 0.7314(3) 0.7502(2) 0.15626(10) 0.0340(6) Uani d . 1 1 . .
    N N9 0.7435(2) 0.8834(2) 0.14768(9) 0.0281(5) Uani d . 1 1 . .
    C C10 0.6401(3) 0.9530(3) 0.11021(12) 0.0347(7) Uani d . 1 1 . .
    H H10A 0.6524 1.0487 0.1150 0.042 Uiso calc R 1 1 . .
    H H10B 0.5466 0.9304 0.1243 0.042 Uiso calc R 1 1 . .
    C C11 0.6530(3) 0.9172(2) 0.04351(12) 0.0278(6) Uani d . 1 1 . .
    C C12 0.7666(4) 0.9615(3) 0.00985(13) 0.0424(8) Uani d . 1 1 . .
    H H12 0.8340 1.0160 0.0278 0.051 Uiso calc R 1 1 . .
    C C13 0.7797(4) 0.9242(3) -0.05091(14) 0.0509(9) Uani d . 1 1 . .
    H H13 0.8563 0.9536 -0.0735 0.061 Uiso calc R 1 1 . .
    C C14 0.6808(4) 0.8446(3) -0.07767(14) 0.0507(9) Uani d . 1 1 . .
    H H14 0.6908 0.8191 -0.1182 0.061 Uiso calc R 1 1 . .
    C C15 0.5672(4) 0.8026(3) -0.04496(15) 0.0511(9) Uani d . 1 1 . .
    H H15 0.4987 0.7502 -0.0635 0.061 Uiso calc R 1 1 . .
    C C16 0.5537(3) 0.8380(3) 0.01595(14) 0.0402(8) Uani d . 1 1 . .
    H H16 0.4770 0.8078 0.0382 0.048 Uiso calc R 1 1 . .
    O O17 1.29867(19) 0.76405(16) 0.30941(8) 0.0286(5) Uani d . 1 1 . .
    C C18 1.4170(3) 0.7600(2) 0.26879(11) 0.0278(6) Uani d . 1 1 . .
    O O19 1.3983(2) 0.86916(16) 0.22727(8) 0.0308(5) Uani d . 1 1 . .
    C C20 1.5517(3) 0.7802(3) 0.30359(13) 0.0360(7) Uani d . 1 1 . .
    H H20A 1.5477 0.8636 0.3252 0.054 Uiso calc R 1 1 . .
    H H20B 1.6292 0.7816 0.2757 0.054 Uiso calc R 1 1 . .
    H H20C 1.5639 0.7084 0.3321 0.054 Uiso calc R 1 1 . .
    C C21 1.4123(3) 0.6299(2) 0.23368(12) 0.0364(7) Uani d . 1 1 . .
    H H21A 1.4858 0.6291 0.2038 0.055 Uiso calc R 1 1 . .
    H H21B 1.3230 0.6216 0.2137 0.055 Uiso calc R 1 1 . .
    H H21C 1.4250 0.5564 0.2613 0.055 Uiso calc R 1 1 . .
    O O3' 1.0121(2) 0.76803(16) 0.33605(8) 0.0283(4) Uani d . 1 1 . .
    C C4' 0.9967(4) 0.8185(3) 0.39562(13) 0.0497(9) Uani d . 1 1 . .
    H H4'1 0.9405 0.8992 0.3945 0.060 Uiso calc R 1 1 . .
    H H4'2 1.0883 0.8413 0.4119 0.060 Uiso calc R 1 1 . .
    C C5' 0.9281(3) 0.7180(2) 0.43610(12) 0.0303(7) Uani d . 1 1 . .
    C C6' 0.9439(4) 0.7281(3) 0.49853(14) 0.0446(8) Uani d . 1 1 . .
    H H6' 0.9965 0.7976 0.5150 0.054 Uiso calc R 1 1 . .
    C C7' 0.8820(4) 0.6357(3) 0.53642(13) 0.0495(9) Uani d . 1 1 . .
    H H7' 0.8924 0.6437 0.5784 0.059 Uiso calc R 1 1 . .
    C C8' 0.8054(4) 0.5322(3) 0.51301(15) 0.0500(9) Uani d . 1 1 . .
    H H8' 0.7648 0.4692 0.5388 0.060 Uiso calc R 1 1 . .
    C C9' 0.7889(4) 0.5223(3) 0.45101(15) 0.0480(9) Uani d . 1 1 . .
    H H9' 0.7360 0.4528 0.4348 0.058 Uiso calc R 1 1 . .
    C C10' 0.8498(3) 0.6139(3) 0.41277(12) 0.0360(7) Uani d . 1 1 . .
    H H10' 0.8383 0.6058 0.3709 0.043 Uiso calc R 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'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 C1 . 1.421(3) ?
    O1 C4 . 1.439(3) ?
    C1 O19 . 1.400(3) ?
    C1 C2 . 1.523(3) ?
    C1 H1 . 0.9800 ?
    C2 O17 . 1.428(3) ?
    C2 C3 . 1.514(4) ?
    C2 H2 . 0.9800 ?
    C3 O3' . 1.414(3) ?
    C3 C4 . 1.529(3) ?
    C3 H3 . 0.9800 ?
    C4 C5 . 1.477(4) ?
    C4 H4 . 0.9800 ?
    C5 N7 . 1.355(3) ?
    C5 C6 . 1.369(3) ?
    C6 N9 . 1.337(3) ?
    C6 H6 . 0.9300 ?
    N7 N8 . 1.330(3) ?
    N8 N9 . 1.351(3) ?
    N9 C10 . 1.460(3) ?
    C10 C11 . 1.513(3) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C16 . 1.374(4) ?
    C11 C12 . 1.383(4) ?
    C12 C13 . 1.391(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.366(4) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.365(5) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.389(4) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    O17 C18 . 1.438(3) ?
    C18 O19 . 1.433(3) ?
    C18 C20 . 1.507(4) ?
    C18 C21 . 1.513(3) ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    O3' C4' . 1.409(3) ?
    C4' C5' . 1.492(4) ?
    C4' H4'1 . 0.9700 ?
    C4' H4'2 . 0.9700 ?
    C5' C10' . 1.379(4) ?
    C5' C6' . 1.382(4) ?
    C6' C7' . 1.376(4) ?
    C6' H6' . 0.9300 ?
    C7' C8' . 1.367(4) ?
    C7' H7' . 0.9300 ?
    C8' C9' . 1.373(4) ?
    C8' H8' . 0.9300 ?
    C9' C10' . 1.371(4) ?
    C9' H9' . 0.9300 ?
    C10' H10' . 0.9300 ?
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
    C1 O1 C4 . . 110.29(18) ?
    O19 C1 O1 . . 112.16(19) ?
    O19 C1 C2 . . 105.47(19) ?
    O1 C1 C2 . . 106.7(2) ?
    O19 C1 H1 . . 110.8 ?
    O1 C1 H1 . . 110.8 ?
    C2 C1 H1 . . 110.8 ?
    O17 C2 C3 . . 109.7(2) ?
    O17 C2 C1 . . 103.1(2) ?
    C3 C2 C1 . . 103.1(2) ?
    O17 C2 H2 . . 113.3 ?
    C3 C2 H2 . . 113.3 ?
    C1 C2 H2 . . 113.3 ?
    O3' C3 C2 . . 115.8(2) ?
    O3' C3 C4 . . 109.82(19) ?
    C2 C3 C4 . . 102.0(2) ?
    O3' C3 H3 . . 109.6 ?
    C2 C3 H3 . . 109.6 ?
    C4 C3 H3 . . 109.6 ?
    O1 C4 C5 . . 108.25(19) ?
    O1 C4 C3 . . 103.10(19) ?
    C5 C4 C3 . . 117.9(2) ?
    O1 C4 H4 . . 109.1 ?
    C5 C4 H4 . . 109.1 ?
    C3 C4 H4 . . 109.1 ?
    N7 C5 C6 . . 108.5(2) ?
    N7 C5 C4 . . 121.3(2) ?
    C6 C5 C4 . . 130.2(2) ?
    N9 C6 C5 . . 105.2(2) ?
    N9 C6 H6 . . 127.4 ?
    C5 C6 H6 . . 127.4 ?
    N8 N7 C5 . . 108.6(2) ?
    N7 N8 N9 . . 106.6(2) ?
    C6 N9 N8 . . 111.0(2) ?
    C6 N9 C10 . . 129.3(2) ?
    N8 N9 C10 . . 119.5(2) ?
    N9 C10 C11 . . 112.1(2) ?
    N9 C10 H10A . . 109.2 ?
    C11 C10 H10A . . 109.2 ?
    N9 C10 H10B . . 109.2 ?
    C11 C10 H10B . . 109.2 ?
    H10A C10 H10B . . 107.9 ?
    C16 C11 C12 . . 119.2(3) ?
    C16 C11 C10 . . 120.5(3) ?
    C12 C11 C10 . . 120.3(3) ?
    C11 C12 C13 . . 119.8(3) ?
    C11 C12 H12 . . 120.1 ?
    C13 C12 H12 . . 120.1 ?
    C14 C13 C12 . . 120.4(3) ?
    C14 C13 H13 . . 119.8 ?
    C12 C13 H13 . . 119.8 ?
    C15 C14 C13 . . 120.0(3) ?
    C15 C14 H14 . . 120.0 ?
    C13 C14 H14 . . 120.0 ?
    C14 C15 C16 . . 120.0(3) ?
    C14 C15 H15 . . 120.0 ?
    C16 C15 H15 . . 120.0 ?
    C11 C16 C15 . . 120.5(3) ?
    C11 C16 H16 . . 119.8 ?
    C15 C16 H16 . . 119.8 ?
    C2 O17 C18 . . 109.46(17) ?
    O19 C18 O17 . . 105.97(19) ?
    O19 C18 C20 . . 109.0(2) ?
    O17 C18 C20 . . 110.5(2) ?
    O19 C18 C21 . . 109.1(2) ?
    O17 C18 C21 . . 108.4(2) ?
    C20 C18 C21 . . 113.5(2) ?
    C1 O19 C18 . . 110.00(19) ?
    C18 C20 H20A . . 109.5 ?
    C18 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C18 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    C18 C21 H21A . . 109.5 ?
    C18 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C18 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C4' O3' C3 . . 113.00(19) ?
    O3' C4' C5' . . 110.9(2) ?
    O3' C4' H4'1 . . 109.5 ?
    C5' C4' H4'1 . . 109.5 ?
    O3' C4' H4'2 . . 109.5 ?
    C5' C4' H4'2 . . 109.5 ?
    H4'1 C4' H4'2 . . 108.0 ?
    C10' C5' C6' . . 118.8(3) ?
    C10' C5' C4' . . 121.6(2) ?
    C6' C5' C4' . . 119.5(3) ?
    C7' C6' C5' . . 120.2(3) ?
    C7' C6' H6' . . 119.9 ?
    C5' C6' H6' . . 119.9 ?
    C8' C7' C6' . . 120.7(3) ?
    C8' C7' H7' . . 119.7 ?
    C6' C7' H7' . . 119.7 ?
    C7' C8' C9' . . 119.2(3) ?
    C7' C8' H8' . . 120.4 ?
    C9' C8' H8' . . 120.4 ?
    C10' C9' C8' . . 120.7(3) ?
    C10' C9' H9' . . 119.7 ?
    C8' C9' H9' . . 119.7 ?
    C9' C10' C5' . . 120.4(3) ?
    C9' C10' H10' . . 119.8 ?
    C5' C10' H10' . . 119.8 ?
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
    C4 O1 C1 O19 . . . . 109.7(2) ?
    C4 O1 C1 C2 . . . . -5.3(3) ?
    O19 C1 C2 O17 . . . . -24.2(2) ?
    O1 C1 C2 O17 . . . . 95.2(2) ?
    O19 C1 C2 C3 . . . . -138.4(2) ?
    O1 C1 C2 C3 . . . . -19.0(3) ?
    O17 C2 C3 O3' . . . . 44.2(3) ?
    C1 C2 C3 O3' . . . . 153.50(19) ?
    O17 C2 C3 C4 . . . . -75.0(2) ?
    C1 C2 C3 C4 . . . . 34.3(2) ?
    C1 O1 C4 C5 . . . . 152.8(2) ?
    C1 O1 C4 C3 . . . . 27.2(3) ?
    O3' C3 C4 O1 . . . . -161.15(19) ?
    C2 C3 C4 O1 . . . . -37.8(2) ?
    O3' C3 C4 C5 . . . . 79.7(3) ?
    C2 C3 C4 C5 . . . . -156.9(2) ?
    O1 C4 C5 N7 . . . . 136.0(2) ?
    C3 C4 C5 N7 . . . . -107.6(3) ?
    O1 C4 C5 C6 . . . . -41.0(4) ?
    C3 C4 C5 C6 . . . . 75.3(3) ?
    N7 C5 C6 N9 . . . . 0.4(3) ?
    C4 C5 C6 N9 . . . . 177.7(2) ?
    C6 C5 N7 N8 . . . . -0.1(3) ?
    C4 C5 N7 N8 . . . . -177.7(2) ?
    C5 N7 N8 N9 . . . . -0.3(3) ?
    C5 C6 N9 N8 . . . . -0.5(3) ?
    C5 C6 N9 C10 . . . . -174.5(2) ?
    N7 N8 N9 C6 . . . . 0.5(3) ?
    N7 N8 N9 C10 . . . . 175.2(2) ?
    C6 N9 C10 C11 . . . . 103.7(3) ?
    N8 N9 C10 C11 . . . . -69.9(3) ?
    N9 C10 C11 C16 . . . . 108.0(3) ?
    N9 C10 C11 C12 . . . . -70.7(3) ?
    C16 C11 C12 C13 . . . . -0.8(4) ?
    C10 C11 C12 C13 . . . . 177.9(3) ?
    C11 C12 C13 C14 . . . . 0.3(5) ?
    C12 C13 C14 C15 . . . . 0.8(5) ?
    C13 C14 C15 C16 . . . . -1.6(5) ?
    C12 C11 C16 C15 . . . . 0.1(4) ?
    C10 C11 C16 C15 . . . . -178.6(3) ?
    C14 C15 C16 C11 . . . . 1.1(5) ?
    C3 C2 O17 C18 . . . . 131.7(2) ?
    C1 C2 O17 C18 . . . . 22.4(2) ?
    C2 O17 C18 O19 . . . . -12.5(2) ?
    C2 O17 C18 C20 . . . . 105.5(2) ?
    C2 O17 C18 C21 . . . . -129.5(2) ?
    O1 C1 O19 C18 . . . . -98.2(2) ?
    C2 C1 O19 C18 . . . . 17.6(3) ?
    O17 C18 O19 C1 . . . . -4.0(3) ?
    C20 C18 O19 C1 . . . . -123.0(2) ?
    C21 C18 O19 C1 . . . . 112.5(2) ?
    C2 C3 O3' C4' . . . . 74.5(3) ?
    C4 C3 O3' C4' . . . . -170.7(3) ?
    C3 O3' C4' C5' . . . . 177.0(2) ?
    O3' C4' C5' C10' . . . . -20.4(4) ?
    O3' C4' C5' C6' . . . . 159.0(3) ?
    C10' C5' C6' C7' . . . . -0.2(5) ?
    C4' C5' C6' C7' . . . . -179.6(3) ?
    C5' C6' C7' C8' . . . . 0.6(5) ?
    C6' C7' C8' C9' . . . . -0.9(5) ?
    C7' C8' C9' C10' . . . . 0.8(5) ?
    C8' C9' C10' C5' . . . . -0.3(5) ?
    C6' C5' C10' C9' . . . . 0.0(5) ?
    C4' C5' C10' C9' . . . . 179.4(3) ?
loop_
    _geom_hbond_atom_site_label_d
    _geom_hbond_atom_site_label_h
    _geom_hbond_atom_site_label_a
    _geom_hbond_site_symmetry_d
    _geom_hbond_site_symmetry_h
    _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
    C21 H21C O19 1_555 1_555 4_845 0.96 2.53 3.285(3) 136 yes
