##############################################################################
###                                                                        ###
###        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/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'manual editing of form.cif'
_journal_date_recd_electronic     2007-06-15
_journal_date_accepted     2007-07-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      8
_journal_page_first     o3484
_journal_page_last     o3484
_journal_paper_category     QO
_journal_coeditor_code     RZ2154
_publ_contact_author
; Matthias Zeller
  Research Fellow and Adjunct Professor
  Department of Chemistry
  Youngstown State University
  1 University Plaza
  Youngstown, OH 44555-3663
  USA
;
_publ_contact_author_email     mzeller@cc.ysu.edu
_publ_contact_author_fax     '(330)941-1579'
_publ_contact_author_phone     '(330)941-7105'
_publ_section_title
;
3,4-Di-O-acetyl-2-azidodeoxy-1-O-nitro-α-L-fucose
;
loop_
    _publ_author_name
    _publ_author_address
    'McCutcheon, David C.'
; Department of Chemistry
  Youngstown State University
  1 University Plaza
  Youngstown, OH 44555-3663
  USA
;
    'Norris, Peter'
; Department of Chemistry
  Youngstown State University
  1 University Plaza
  Youngstown, OH 44555-3663
  USA
;
    'Zeller, Matthias'
; Department of Chemistry
  Youngstown State University
  1 University Plaza
  Youngstown, OH 44555-3663
  USA
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3,4-Di-O-acetyl-2-azidodeoxy-1-O-nitro-α-L-fucose
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H14 N4 O8'
_chemical_formula_sum     'C10 H14 N4 O8'
_chemical_formula_iupac     'C10 H14 N4 O8'
_chemical_formula_weight     318.25
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     8.2169(6)
_cell_length_b     15.8825(12)
_cell_length_c     21.7738(16)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2841.6(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     8591
_cell_measurement_theta_min     2.27
_cell_measurement_theta_max     30.54
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.52
_exptl_crystal_size_mid     0.50
_exptl_crystal_size_min     0.36
_exptl_crystal_density_diffrn     1.488
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1328
_exptl_absorpt_coefficient_mu     0.130
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS in SAINT-Plus; Bruker, 2003)'
_exptl_absorpt_correction_T_min     0.783
_exptl_absorpt_correction_T_max     0.954
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     100(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 APEX CCD diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     25826
_diffrn_reflns_av_R_equivalents     0.0568
_diffrn_reflns_av_sigmaI/netI     0.0341
_diffrn_reflns_theta_min     1.59
_diffrn_reflns_theta_max     28.28
_diffrn_reflns_theta_full     28.28
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -28
_diffrn_reflns_limit_l_max     28
_diffrn_standards_number     0
_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 > 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     3960
_reflns_number_gt     3777
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0348
_refine_ls_R_factor_gt     0.0330
_refine_ls_wR_factor_gt     0.0825
_refine_ls_wR_factor_ref     0.0840
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.047
_refine_ls_number_reflns     3960
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0432P)²+0.6271P] 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     0.273
_refine_diff_density_min     -0.183
_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'
    '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     'SMART (Bruker, 2002)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2003)'
_computing_data_reduction     'SAINT-Plus'
_computing_structure_solution     'SHELXTL (Bruker, 2003)'
_computing_structure_refinement     SHELXTL
_computing_molecular_graphics     SHELXTL
_computing_publication_material     SHELXTL
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
    C C1A 0.1519(2) 0.68931(11) 0.96074(8) 0.0173(3) Uani d . 1 . .
    H H1A 0.1697 0.6907 1.0062 0.021 Uiso calc R 1 . .
    C C2A 0.3138(2) 0.70045(11) 0.92821(8) 0.0165(3) Uani d . 1 . .
    H H2A 0.3653 0.7545 0.9416 0.020 Uiso calc R 1 . .
    C C3A 0.2871(2) 0.70192(11) 0.85901(8) 0.0160(3) Uani d . 1 . .
    H H3A 0.2445 0.6460 0.8452 0.019 Uiso calc R 1 . .
    C C4A 0.1645(2) 0.77066(11) 0.84250(8) 0.0171(3) Uani d . 1 . .
    H H4A 0.1394 0.7679 0.7976 0.021 Uiso calc R 1 . .
    C C5A 0.0083(2) 0.75793(11) 0.87924(8) 0.0178(3) Uani d . 1 . .
    H H5A -0.0439 0.7043 0.8654 0.021 Uiso calc R 1 . .
    C C6A -0.1136(2) 0.82860(12) 0.87166(9) 0.0234(4) Uani d . 1 . .
    H H6A1 -0.0730 0.8792 0.8924 0.035 Uiso calc R 1 . .
    H H6A2 -0.2178 0.8119 0.8898 0.035 Uiso calc R 1 . .
    H H6A3 -0.1288 0.8405 0.8279 0.035 Uiso calc R 1 . .
    C C7A 0.4653(2) 0.68822(11) 0.77365(8) 0.0180(3) Uani d . 1 . .
    C C8A 0.6392(2) 0.69823(12) 0.75485(9) 0.0233(4) Uani d . 1 . .
    H H8A1 0.6533 0.6775 0.7128 0.035 Uiso calc R 1 . .
    H H8A2 0.7089 0.6659 0.7827 0.035 Uiso calc R 1 . .
    H H8A3 0.6694 0.7579 0.7567 0.035 Uiso calc R 1 . .
    C C9A 0.3093(3) 0.89460(12) 0.81195(9) 0.0230(4) Uani d . 1 . .
    C C10A 0.3549(3) 0.98127(13) 0.83182(10) 0.0301(5) Uani d . 1 . .
    H H10A 0.2568 1.0161 0.8347 0.045 Uiso calc R 1 . .
    H H10B 0.4297 1.0060 0.8018 0.045 Uiso calc R 1 . .
    H H10C 0.4082 0.9787 0.8720 0.045 Uiso calc R 1 . .
    C C1B 0.2547(2) 0.43484(11) 0.79007(8) 0.0180(3) Uani d . 1 . .
    H H1B 0.3018 0.4367 0.7477 0.022 Uiso calc R 1 . .
    C C2B 0.3935(2) 0.43329(11) 0.83734(8) 0.0178(3) Uani d . 1 . .
    H H2B 0.4627 0.3826 0.8297 0.021 Uiso calc R 1 . .
    C C3B 0.3204(2) 0.42703(11) 0.90164(8) 0.0163(3) Uani d . 1 . .
    H H3B 0.2521 0.4777 0.9105 0.020 Uiso calc R 1 . .
    C C4B 0.2164(2) 0.34711(11) 0.90480(8) 0.0175(3) Uani d . 1 . .
    H H4B 0.1664 0.3415 0.9465 0.021 Uiso calc R 1 . .
    C C5B 0.0837(2) 0.35172(11) 0.85600(8) 0.0178(3) Uani d . 1 . .
    H H5B 0.0102 0.4000 0.8660 0.021 Uiso calc R 1 . .
    C C6B -0.0187(3) 0.27262(13) 0.85109(9) 0.0251(4) Uani d . 1 . .
    H H6B1 0.0490 0.2262 0.8361 0.038 Uiso calc R 1 . .
    H H6B2 -0.1086 0.2823 0.8224 0.038 Uiso calc R 1 . .
    H H6B3 -0.0624 0.2582 0.8916 0.038 Uiso calc R 1 . .
    C C7B 0.4189(2) 0.44343(11) 1.00306(8) 0.0198(4) Uani d . 1 . .
    C C8B 0.5676(3) 0.43756(15) 1.04241(10) 0.0304(4) Uani d . 1 . .
    H H8B1 0.5360 0.4401 1.0858 0.046 Uiso calc R 1 . .
    H H8B2 0.6407 0.4845 1.0329 0.046 Uiso calc R 1 . .
    H H8B3 0.6234 0.3842 1.0343 0.046 Uiso calc R 1 . .
    C C9B 0.3866(2) 0.23554(11) 0.94182(9) 0.0204(4) Uani d . 1 . .
    C C10B 0.5124(3) 0.17257(13) 0.92196(10) 0.0274(4) Uani d . 1 . .
    H H10D 0.4929 0.1189 0.9428 0.041 Uiso calc R 1 . .
    H H10E 0.6210 0.1934 0.9326 0.041 Uiso calc R 1 . .
    H H10F 0.5054 0.1644 0.8774 0.041 Uiso calc R 1 . .
    N N1A -0.0035(2) 0.56522(10) 0.98752(7) 0.0216(3) Uani d . 1 . .
    N N2A 0.41780(19) 0.62882(10) 0.94692(7) 0.0184(3) Uani d . 1 . .
    N N3A 0.5655(2) 0.64117(10) 0.94132(7) 0.0206(3) Uani d . 1 . .
    N N4A 0.7021(2) 0.64433(12) 0.93857(10) 0.0313(4) Uani d . 1 . .
    N N1B 0.0763(2) 0.54341(10) 0.75172(7) 0.0226(3) Uani d . 1 . .
    N N2B 0.4937(2) 0.50950(10) 0.82922(8) 0.0209(3) Uani d . 1 . .
    N N3B 0.6420(2) 0.49697(10) 0.83443(8) 0.0230(3) Uani d . 1 . .
    N N4B 0.7785(2) 0.49429(13) 0.83732(11) 0.0374(5) Uani d . 1 . .
    O O1A 0.04098(16) 0.75143(8) 0.94464(6) 0.0181(3) Uani d . 1 . .
    O O2A 0.09418(16) 0.60611(8) 0.94303(6) 0.0188(3) Uani d . 1 . .
    O O3A 0.44471(16) 0.71616(8) 0.83227(6) 0.0181(3) Uani d . 1 . .
    O O4A 0.22958(17) 0.85305(8) 0.85736(6) 0.0191(3) Uani d . 1 . .
    O O5A -0.0240(2) 0.59973(10) 1.03602(7) 0.0311(3) Uani d . 1 . .
    O O6A -0.05346(18) 0.49872(9) 0.96954(7) 0.0280(3) Uani d . 1 . .
    O O7A 0.35749(18) 0.65942(9) 0.74306(6) 0.0237(3) Uani d . 1 . .
    O O8A 0.3355(2) 0.86470(9) 0.76178(7) 0.0311(3) Uani d . 1 . .
    O O1B 0.15313(16) 0.36579(8) 0.79517(6) 0.0189(3) Uani d . 1 . .
    O O2B 0.16796(16) 0.51307(8) 0.80211(6) 0.0194(3) Uani d . 1 . .
    O O3B 0.45529(16) 0.42301(8) 0.94370(6) 0.0191(3) Uani d . 1 . .
    O O4B 0.32046(16) 0.27581(8) 0.89237(6) 0.0180(3) Uani d . 1 . .
    O O5B 0.0821(2) 0.50576(10) 0.70412(7) 0.0371(4) Uani d . 1 . .
    O O6B 0.00131(18) 0.60629(9) 0.76422(7) 0.0265(3) Uani d . 1 . .
    O O7B 0.28545(17) 0.46294(9) 1.01992(6) 0.0228(3) Uani d . 1 . .
    O O8B 0.3492(2) 0.25016(10) 0.99387(7) 0.0291(3) Uani d . 1 . .
_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
    C1A O1A . 1.388(2) ?
    C1A O2A . 1.456(2) ?
    C1A C2A . 1.518(2) ?
    C1A H1A . 1.0000 ?
    C2A N2A . 1.480(2) ?
    C2A C3A . 1.523(2) ?
    C2A H2A . 1.0000 ?
    C3A O3A . 1.438(2) ?
    C3A C4A . 1.529(2) ?
    C3A H3A . 1.0000 ?
    C4A O4A . 1.450(2) ?
    C4A C5A . 1.526(2) ?
    C4A H4A . 1.0000 ?
    C5A O1A . 1.453(2) ?
    C5A C6A . 1.513(3) ?
    C5A H5A . 1.0000 ?
    C6A H6A1 . 0.9800 ?
    C6A H6A2 . 0.9800 ?
    C6A H6A3 . 0.9800 ?
    C7A O7A . 1.199(2) ?
    C7A O3A . 1.362(2) ?
    C7A C8A . 1.495(3) ?
    C8A H8A1 . 0.9800 ?
    C8A H8A2 . 0.9800 ?
    C8A H8A3 . 0.9800 ?
    C9A O8A . 1.210(2) ?
    C9A O4A . 1.357(2) ?
    C9A C10A . 1.491(3) ?
    C10A H10A . 0.9800 ?
    C10A H10B . 0.9800 ?
    C10A H10C . 0.9800 ?
    C1B O1B . 1.383(2) ?
    C1B O2B . 1.456(2) ?
    C1B C2B . 1.536(2) ?
    C1B H1B . 1.0000 ?
    C2B N2B . 1.474(2) ?
    C2B C3B . 1.527(2) ?
    C2B H2B . 1.0000 ?
    C3B O3B . 1.440(2) ?
    C3B C4B . 1.532(2) ?
    C3B H3B . 1.0000 ?
    C4B O4B . 1.445(2) ?
    C4B C5B . 1.524(2) ?
    C4B H4B . 1.0000 ?
    C5B O1B . 1.459(2) ?
    C5B C6B . 1.516(3) ?
    C5B H5B . 1.0000 ?
    C6B H6B1 . 0.9800 ?
    C6B H6B2 . 0.9800 ?
    C6B H6B3 . 0.9800 ?
    C7B O7B . 1.197(2) ?
    C7B O3B . 1.366(2) ?
    C7B C8B . 1.495(3) ?
    C8B H8B1 . 0.9800 ?
    C8B H8B2 . 0.9800 ?
    C8B H8B3 . 0.9800 ?
    C9B O8B . 1.197(2) ?
    C9B O4B . 1.365(2) ?
    C9B C10B . 1.502(3) ?
    C10B H10D . 0.9800 ?
    C10B H10E . 0.9800 ?
    C10B H10F . 0.9800 ?
    N1A O6A . 1.199(2) ?
    N1A O5A . 1.202(2) ?
    N1A O2A . 1.4158(19) ?
    N2A N3A . 1.236(2) ?
    N3A N4A . 1.125(2) ?
    N1B O5B . 1.198(2) ?
    N1B O6B . 1.204(2) ?
    N1B O2B . 1.4156(19) ?
    N2B N3B . 1.240(2) ?
    N3B N4B . 1.124(3) ?
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
    O1A C1A O2A . . 111.38(14) ?
    O1A C1A C2A . . 112.01(14) ?
    O2A C1A C2A . . 105.52(14) ?
    O1A C1A H1A . . 109.3 ?
    O2A C1A H1A . . 109.3 ?
    C2A C1A H1A . . 109.3 ?
    N2A C2A C1A . . 106.74(14) ?
    N2A C2A C3A . . 111.55(14) ?
    C1A C2A C3A . . 109.69(15) ?
    N2A C2A H2A . . 109.6 ?
    C1A C2A H2A . . 109.6 ?
    C3A C2A H2A . . 109.6 ?
    O3A C3A C2A . . 105.84(14) ?
    O3A C3A C4A . . 112.72(13) ?
    C2A C3A C4A . . 109.80(14) ?
    O3A C3A H3A . . 109.5 ?
    C2A C3A H3A . . 109.5 ?
    C4A C3A H3A . . 109.5 ?
    O4A C4A C5A . . 108.24(14) ?
    O4A C4A C3A . . 110.41(14) ?
    C5A C4A C3A . . 109.66(14) ?
    O4A C4A H4A . . 109.5 ?
    C5A C4A H4A . . 109.5 ?
    C3A C4A H4A . . 109.5 ?
    O1A C5A C6A . . 106.39(14) ?
    O1A C5A C4A . . 111.57(14) ?
    C6A C5A C4A . . 113.64(15) ?
    O1A C5A H5A . . 108.4 ?
    C6A C5A H5A . . 108.4 ?
    C4A C5A H5A . . 108.4 ?
    C5A C6A H6A1 . . 109.5 ?
    C5A C6A H6A2 . . 109.5 ?
    H6A1 C6A H6A2 . . 109.5 ?
    C5A C6A H6A3 . . 109.5 ?
    H6A1 C6A H6A3 . . 109.5 ?
    H6A2 C6A H6A3 . . 109.5 ?
    O7A C7A O3A . . 123.58(17) ?
    O7A C7A C8A . . 126.49(17) ?
    O3A C7A C8A . . 109.92(16) ?
    C7A C8A H8A1 . . 109.5 ?
    C7A C8A H8A2 . . 109.5 ?
    H8A1 C8A H8A2 . . 109.5 ?
    C7A C8A H8A3 . . 109.5 ?
    H8A1 C8A H8A3 . . 109.5 ?
    H8A2 C8A H8A3 . . 109.5 ?
    O8A C9A O4A . . 123.53(18) ?
    O8A C9A C10A . . 125.42(18) ?
    O4A C9A C10A . . 111.03(16) ?
    C9A C10A H10A . . 109.5 ?
    C9A C10A H10B . . 109.5 ?
    H10A C10A H10B . . 109.5 ?
    C9A C10A H10C . . 109.5 ?
    H10A C10A H10C . . 109.5 ?
    H10B C10A H10C . . 109.5 ?
    O1B C1B O2B . . 111.51(14) ?
    O1B C1B C2B . . 112.43(14) ?
    O2B C1B C2B . . 104.85(14) ?
    O1B C1B H1B . . 109.3 ?
    O2B C1B H1B . . 109.3 ?
    C2B C1B H1B . . 109.3 ?
    N2B C2B C3B . . 112.53(15) ?
    N2B C2B C1B . . 108.72(14) ?
    C3B C2B C1B . . 108.86(15) ?
    N2B C2B H2B . . 108.9 ?
    C3B C2B H2B . . 108.9 ?
    C1B C2B H2B . . 108.9 ?
    O3B C3B C2B . . 106.45(14) ?
    O3B C3B C4B . . 111.37(14) ?
    C2B C3B C4B . . 108.34(14) ?
    O3B C3B H3B . . 110.2 ?
    C2B C3B H3B . . 110.2 ?
    C4B C3B H3B . . 110.2 ?
    O4B C4B C5B . . 109.31(14) ?
    O4B C4B C3B . . 108.11(14) ?
    C5B C4B C3B . . 109.14(14) ?
    O4B C4B H4B . . 110.1 ?
    C5B C4B H4B . . 110.1 ?
    C3B C4B H4B . . 110.1 ?
    O1B C5B C6B . . 106.25(14) ?
    O1B C5B C4B . . 111.12(14) ?
    C6B C5B C4B . . 113.97(15) ?
    O1B C5B H5B . . 108.5 ?
    C6B C5B H5B . . 108.5 ?
    C4B C5B H5B . . 108.5 ?
    C5B C6B H6B1 . . 109.5 ?
    C5B C6B H6B2 . . 109.5 ?
    H6B1 C6B H6B2 . . 109.5 ?
    C5B C6B H6B3 . . 109.5 ?
    H6B1 C6B H6B3 . . 109.5 ?
    H6B2 C6B H6B3 . . 109.5 ?
    O7B C7B O3B . . 123.52(17) ?
    O7B C7B C8B . . 126.08(18) ?
    O3B C7B C8B . . 110.40(16) ?
    C7B C8B H8B1 . . 109.5 ?
    C7B C8B H8B2 . . 109.5 ?
    H8B1 C8B H8B2 . . 109.5 ?
    C7B C8B H8B3 . . 109.5 ?
    H8B1 C8B H8B3 . . 109.5 ?
    H8B2 C8B H8B3 . . 109.5 ?
    O8B C9B O4B . . 123.61(18) ?
    O8B C9B C10B . . 125.35(18) ?
    O4B C9B C10B . . 111.03(16) ?
    C9B C10B H10D . . 109.5 ?
    C9B C10B H10E . . 109.5 ?
    H10D C10B H10E . . 109.5 ?
    C9B C10B H10F . . 109.5 ?
    H10D C10B H10F . . 109.5 ?
    H10E C10B H10F . . 109.5 ?
    O6A N1A O5A . . 129.84(17) ?
    O6A N1A O2A . . 112.01(15) ?
    O5A N1A O2A . . 118.14(16) ?
    N3A N2A C2A . . 114.70(15) ?
    N4A N3A N2A . . 172.9(2) ?
    O5B N1B O6B . . 129.07(17) ?
    O5B N1B O2B . . 118.64(15) ?
    O6B N1B O2B . . 112.29(15) ?
    N3B N2B C2B . . 113.95(16) ?
    N4B N3B N2B . . 172.6(2) ?
    C1A O1A C5A . . 114.81(13) ?
    N1A O2A C1A . . 114.81(13) ?
    C7A O3A C3A . . 116.11(14) ?
    C9A O4A C4A . . 117.02(14) ?
    C1B O1B C5B . . 115.50(13) ?
    N1B O2B C1B . . 114.29(13) ?
    C7B O3B C3B . . 115.02(14) ?
    C9B O4B C4B . . 117.08(14) ?
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
    O1A C1A C2A N2A . . . . -177.50(14) ?
    O2A C1A C2A N2A . . . . -56.15(17) ?
    O1A C1A C2A C3A . . . . -56.49(19) ?
    O2A C1A C2A C3A . . . . 64.86(16) ?
    N2A C2A C3A O3A . . . . -64.30(17) ?
    C1A C2A C3A O3A . . . . 177.64(13) ?
    N2A C2A C3A C4A . . . . 173.77(14) ?
    C1A C2A C3A C4A . . . . 55.71(18) ?
    O3A C3A C4A O4A . . . . -53.14(18) ?
    C2A C3A C4A O4A . . . . 64.59(18) ?
    O3A C3A C4A C5A . . . . -172.32(14) ?
    C2A C3A C4A C5A . . . . -54.59(19) ?
    O4A C4A C5A O1A . . . . -67.51(17) ?
    C3A C4A C5A O1A . . . . 53.00(19) ?
    O4A C4A C5A C6A . . . . 52.77(19) ?
    C3A C4A C5A C6A . . . . 173.28(15) ?
    O1B C1B C2B N2B . . . . -179.13(14) ?
    O2B C1B C2B N2B . . . . -57.80(17) ?
    O1B C1B C2B C3B . . . . -56.22(19) ?
    O2B C1B C2B C3B . . . . 65.10(17) ?
    N2B C2B C3B O3B . . . . -61.27(18) ?
    C1B C2B C3B O3B . . . . 178.14(13) ?
    N2B C2B C3B C4B . . . . 178.85(14) ?
    C1B C2B C3B C4B . . . . 58.26(18) ?
    O3B C3B C4B O4B . . . . -56.78(17) ?
    C2B C3B C4B O4B . . . . 59.97(17) ?
    O3B C3B C4B C5B . . . . -175.58(14) ?
    C2B C3B C4B C5B . . . . -58.83(18) ?
    O4B C4B C5B O1B . . . . -62.93(18) ?
    C3B C4B C5B O1B . . . . 55.12(18) ?
    O4B C4B C5B C6B . . . . 57.07(19) ?
    C3B C4B C5B C6B . . . . 175.12(15) ?
    C1A C2A N2A N3A . . . . -157.79(16) ?
    C3A C2A N2A N3A . . . . 82.4(2) ?
    C3B C2B N2B N3B . . . . 99.33(19) ?
    C1B C2B N2B N3B . . . . -140.00(17) ?
    O2A C1A O1A C5A . . . . -61.11(19) ?
    C2A C1A O1A C5A . . . . 56.80(19) ?
    C6A C5A O1A C1A . . . . -179.81(14) ?
    C4A C5A O1A C1A . . . . -55.36(19) ?
    O6A N1A O2A C1A . . . . 176.94(15) ?
    O5A N1A O2A C1A . . . . -3.3(2) ?
    O1A C1A O2A N1A . . . . -88.22(17) ?
    C2A C1A O2A N1A . . . . 150.01(14) ?
    O7A C7A O3A C3A . . . . 5.9(2) ?
    C8A C7A O3A C3A . . . . -173.41(14) ?
    C2A C3A O3A C7A . . . . 155.22(14) ?
    C4A C3A O3A C7A . . . . -84.75(18) ?
    O8A C9A O4A C4A . . . . -4.0(3) ?
    C10A C9A O4A C4A . . . . 174.42(16) ?
    C5A C4A O4A C9A . . . . -147.08(16) ?
    C3A C4A O4A C9A . . . . 92.88(18) ?
    O2B C1B O1B C5B . . . . -62.93(18) ?
    C2B C1B O1B C5B . . . . 54.51(19) ?
    C6B C5B O1B C1B . . . . -178.66(15) ?
    C4B C5B O1B C1B . . . . -54.18(19) ?
    O5B N1B O2B C1B . . . . -2.9(2) ?
    O6B N1B O2B C1B . . . . 177.26(15) ?
    O1B C1B O2B N1B . . . . -80.51(17) ?
    C2B C1B O2B N1B . . . . 157.57(14) ?
    O7B C7B O3B C3B . . . . 0.4(3) ?
    C8B C7B O3B C3B . . . . -179.70(15) ?
    C2B C3B O3B C7B . . . . 160.42(14) ?
    C4B C3B O3B C7B . . . . -81.68(18) ?
    O8B C9B O4B C4B . . . . 8.5(3) ?
    C10B C9B O4B C4B . . . . -170.63(15) ?
    C5B C4B O4B C9B . . . . -147.23(15) ?
    C3B C4B O4B C9B . . . . 94.07(17) ?
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
    C10A H10C O5A 4_567 0.98 2.42 3.305(3) 149.6
    C8A H8A3 O1B 3_656 0.98 2.52 3.344(2) 141.8
    C5B H5B N4B 1_455 1.00 2.50 3.403(3) 149.8
    C4B H4B O8B . 1.00 2.33 2.706(2) 101.1
    C3B H3B O2A . 1.00 2.52 3.515(2) 174.3
    C3A H3A O2B . 1.00 2.40 3.390(2) 172.7
    C2B H2B O4B . 1.00 2.47 2.838(2) 101.1
    C2A H2A O5A 4_567 1.00 2.54 3.529(2) 172.6
