##############################################################################
###                                                                        ###
###        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/  #
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data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2009-06-16
_journal_date_accepted     2009-06-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      8
_journal_page_first     o1781
_journal_page_last     o1782
_journal_paper_category     QO
_journal_coeditor_code     IS2433
_publ_contact_author_name     'Dr Masahisa Wada'
_publ_contact_author_address
;
Department of Biomaterials Science
Graduate School of Agricultural and Life Science
The University of Tokyo
Yayoi 1-1-1
Bunkyo-ku
Tokyo 113-8657
Japan
;
_publ_contact_author_email     'awadam@mail.ecc.u-tokyo.ac.jp'
_publ_contact_author_fax     '81(35841)2677'
_publ_contact_author_phone     '81(35841)5247'
_publ_section_title
;
2-Acetamido-2-deoxy-3-<i>O</i>-\b-<i>D</i>-galactopyranosyl-<i>D</i>-glucose
dihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Wada, Masahisa'
;
    Department of Biomaterials Science
    Graduate School of Agricultural and Life Science
    The University of Tokyo
    Yayoi 1-1-1
    Bunkyo-ku
    Tokyo 113-8657
    Japan
;
    'Kobayashi, Kayoko'
;
    Department of Biomaterials Science
    Graduate School of Agricultural and Life Science
    The University of Tokyo
    Yayoi 1-1-1
    Bunkyo-ku
    Tokyo 113-8657
    Japan
;
    'Nishimoto, Mamoru'
;
    National Food Reserch Institute
    National Agriculture and Food Research Organization
    2-1-12 Kanondai
    Tsukuba
    Ibaraki 305-8642
    Japan
;
    'Kitaoka, Motomitsu'
;
    National Food Reserch Institute
    National Agriculture and Food Research Organization
    2-1-12 Kanondai
    Tsukuba
    Ibaraki 305-8642
    Japan
;
    'Noguchi, Keiichi'
;
    Instrumentaion Analysis Center
    Tokyo University of Agriculture & Technology
    2-24-16 Naka-cho
    Koganei
    Tokyo 184-8588
    Japan
;
data_I
_chemical_name_systematic
;
2-Acetamido-2-deoxy-3-<i>O</i>-\b-D-galactopyranosyl-D-
glucose dihydrate
;
_chemical_name_common     'lacto-N-biose I dihydrate'
_chemical_formula_moiety     'C14 H25 N O11, 2(H2 O)'
_chemical_formula_sum     'C14 H29 N O13'
_chemical_formula_iupac     'C14 H25 N O11, 2H2 O'
_chemical_formula_weight     419.38
_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_site_id
    _symmetry_equiv_pos_as_xyz
    1 'x, y, z'
    2 '-x+1/2, -y, z+1/2'
    3 'x+1/2, -y+1/2, -z'
    4 '-x, y+1/2, -z+1/2'
_cell_length_a     8.2840(10)
_cell_length_b     12.8410(10)
_cell_length_c     17.5030(10)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1861.9(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25787
_cell_measurement_theta_min     2.21
_cell_measurement_theta_max     30.01
_cell_measurement_temperature     95(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.10
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.496
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     896
_exptl_absorpt_coefficient_mu     0.132
_exptl_absorpt_correction_type     none
_diffrn_ambient_temperature     95(2)
_diffrn_radiation_type     synchrotron
_diffrn_radiation_wavelength     0.80000
_diffrn_radiation_source     'Photon Facrory NW12A'
_diffrn_radiation_monochromator     silicon
_diffrn_measurement_device_type     'ADSC Quantum 210r'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     9.7466
_diffrn_reflns_number     25787
_diffrn_reflns_av_R_equivalents     0.0470
_diffrn_reflns_av_sigmaI/netI     0.0189
_diffrn_reflns_theta_min     2.21
_diffrn_reflns_theta_max     30.01
_diffrn_reflns_theta_full     30.01
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     2153
_reflns_number_gt     2046
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0440
_refine_ls_R_factor_gt     0.0421
_refine_ls_wR_factor_gt     0.1137
_refine_ls_wR_factor_ref     0.1153
_refine_ls_goodness_of_fit_ref     1.063
_refine_ls_restrained_S_all     1.063
_refine_ls_number_reflns     2153
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0806P)^2^+0.7215P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     difmap&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     0.272
_refine_diff_density_min     -0.309
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.084(6)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0040 0.0020
                         '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' 0.0080 0.0040
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0140 0.0080
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
<i>UGUI</i> (Structural Biology Research Center, 2005)
;
_computing_cell_refinement     'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction     'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS86 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEPIII (Burnett & Johnson, 1996)'
_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
    C C1 0.7021(3) 0.32502(19) 0.34879(14) 0.0205(5) Uani d . 1 . .
    H H1 0.8227 0.3214 0.3471 0.025 Uiso calc R 1 . .
    C C2 0.6435(3) 0.4253(2) 0.31127(15) 0.0211(5) Uani d . 1 . .
    H H2 0.5234 0.4232 0.3059 0.025 Uiso calc R 1 . .
    C C3 0.6921(3) 0.52070(19) 0.35853(15) 0.0215(5) Uani d . 1 . .
    H H3 0.8113 0.5310 0.3535 0.026 Uiso calc R 1 . .
    C C4 0.6518(3) 0.5082(2) 0.44263(16) 0.0226(6) Uani d . 1 . .
    H H4 0.7071 0.5646 0.4721 0.027 Uiso calc R 1 . .
    C C5 0.7119(4) 0.4031(2) 0.47122(15) 0.0235(6) Uani d . 1 . .
    H H5 0.8323 0.4017 0.4671 0.028 Uiso calc R 1 . .
    C C6 0.6658(4) 0.3832(2) 0.55375(16) 0.0279(6) Uani d . 1 . .
    H H61 0.6722 0.4494 0.5826 0.033 Uiso calc R 1 . .
    H H62 0.5526 0.3585 0.5559 0.033 Uiso calc R 1 . .
    O O1 0.6358(2) 0.24111(13) 0.30922(11) 0.0217(4) Uani d . 1 B .
    O O2 0.7150(2) 0.43673(14) 0.23805(11) 0.0241(4) Uani d . 1 . .
    H H2O 0.6648 0.4055 0.2024 0.029 Uiso d R 1 . .
    O O3 0.6135(3) 0.61167(14) 0.33229(11) 0.0261(5) Uani d . 1 . .
    H H3O 0.6709 0.6420 0.2988 0.031 Uiso d R 1 . .
    O O4 0.4818(3) 0.51573(15) 0.45519(11) 0.0268(5) Uani d . 1 . .
    H H4O 0.4508 0.5788 0.4331 0.032 Uiso d R 1 . .
    O O5 0.6475(2) 0.31996(13) 0.42597(10) 0.0219(4) Uani d . 1 . .
    O O6 0.7678(3) 0.30802(14) 0.58916(11) 0.0266(5) Uani d . 1 . .
    H H6O 0.7491 0.2462 0.5742 0.032 Uiso d R 1 . .
    C C7 0.8597(3) -0.00264(19) 0.25298(15) 0.0220(5) Uani d . 1 . .
    H H71 0.8919 -0.0327 0.2025 0.026 Uiso calc PR 0.77 A 1
    H H72 0.9533 0.0120 0.2874 0.026 Uiso d PR 0.23 A 2
    C C8 0.7699(3) 0.10082(19) 0.24040(15) 0.0213(5) Uani d . 1 B .
    H H8 0.6707 0.0870 0.2094 0.026 Uiso calc R 1 . .
    C C9 0.7191(3) 0.14403(19) 0.31837(15) 0.0206(5) Uani d . 1 . .
    H H9 0.8171 0.1549 0.3508 0.025 Uiso calc R 1 B .
    C C10 0.6100(3) 0.06275(19) 0.35568(15) 0.0213(5) Uani d . 1 B .
    H H10 0.5151 0.0491 0.3218 0.026 Uiso calc R 1 . .
    C C11 0.7058(3) -0.03748(19) 0.36589(15) 0.0218(5) Uani d . 1 . .
    H H11 0.8047 -0.0211 0.3964 0.026 Uiso calc R 1 B .
    C C12 0.6157(4) -0.1242(2) 0.40603(16) 0.0248(6) Uani d . 1 B .
    H H121 0.6855 -0.1866 0.4092 0.030 Uiso calc R 1 . .
    H H122 0.5888 -0.1022 0.4587 0.030 Uiso calc R 1 . .
    O O71 0.9959(3) 0.01943(18) 0.29538(14) 0.0217(5) Uani d P 0.77 B 1
    H H71O 1.0752 -0.0218 0.2860 0.026 Uiso d PR 0.77 B 1
    O O72 0.9226(12) -0.0517(7) 0.1856(5) 0.031(2) Uani d P 0.23 B 2
    H H72O 0.8861 -0.0216 0.1467 0.037 Uiso d PR 0.23 B 2
    O O10 0.5548(3) 0.09459(15) 0.42885(11) 0.0251(5) Uani d . 1 . .
    H H10O 0.4729 0.1468 0.4241 0.030 Uiso d R 1 B .
    O O11 0.7561(2) -0.07395(14) 0.29198(11) 0.0229(4) Uani d . 1 B .
    O O12 0.4722(3) -0.1495(2) 0.36648(17) 0.0485(7) Uani d . 1 . .
    H H12O 0.4325 -0.2091 0.3760 0.058 Uiso d R 1 B .
    N N1 0.8734(3) 0.17181(16) 0.19831(13) 0.0214(5) Uani d . 1 . .
    H H1N 0.9621 0.1942 0.2205 0.026 Uiso calc R 1 B .
    C C13 0.8410(3) 0.20474(19) 0.12798(16) 0.0220(6) Uani d . 1 B .
    O O13 0.7167(3) 0.18034(14) 0.09211(11) 0.0258(4) Uani d . 1 . .
    C C14 0.9628(4) 0.2771(2) 0.09275(17) 0.0312(7) Uani d . 1 . .
    H H141 1.0519 0.2884 0.1287 0.047 Uiso calc R 1 B .
    H H142 0.9112 0.3438 0.0810 0.047 Uiso calc R 1 . .
    H H143 1.0048 0.2461 0.0456 0.047 Uiso calc R 1 . .
    O O1W 0.2143(3) 0.39008(16) 0.43738(13) 0.0370(6) Uani d . 1 . .
    H H11W 0.1688 0.3974 0.4806 0.044 Uiso d R 1 . .
    H H12W 0.2950 0.4330 0.4398 0.044 Uiso d R 1 . .
    O O2W 0.8087(2) 0.72473(14) 0.24058(11) 0.0247(4) Uani d . 1 . .
    H H21W 0.7630 0.7867 0.2498 0.030 Uiso d R 1 . .
    H H22W 0.7901 0.7083 0.1942 0.030 Uiso d 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
    C1 0.0228(13) 0.0155(11) 0.0234(12) -0.0008(11) 0.0008(11) -0.0003(9)
    C2 0.0226(13) 0.0174(12) 0.0234(12) -0.0030(10) 0.0052(11) 0.0017(10)
    C3 0.0216(12) 0.0146(11) 0.0284(13) -0.0008(10) 0.0015(11) 0.0010(10)
    C4 0.0235(13) 0.0161(11) 0.0282(13) 0.0002(11) 0.0020(11) 0.0000(10)
    C5 0.0270(13) 0.0168(11) 0.0266(13) -0.0004(11) -0.0002(11) 0.0000(10)
    C6 0.0334(16) 0.0232(13) 0.0271(14) 0.0061(12) 0.0018(12) 0.0011(11)
    O1 0.0240(10) 0.0130(8) 0.0280(9) 0.0006(8) -0.0020(8) -0.0001(7)
    O2 0.0269(10) 0.0221(9) 0.0233(9) -0.0041(8) 0.0020(8) 0.0008(7)
    O3 0.0302(11) 0.0151(8) 0.0329(10) 0.0033(8) 0.0029(9) 0.0043(7)
    O4 0.0272(10) 0.0196(9) 0.0336(10) 0.0058(8) 0.0065(9) 0.0026(8)
    O5 0.0286(10) 0.0147(8) 0.0225(9) 0.0002(8) 0.0013(8) -0.0005(7)
    O6 0.0311(11) 0.0193(9) 0.0293(10) 0.0021(8) -0.0036(8) 0.0022(8)
    C7 0.0244(13) 0.0165(11) 0.0251(12) -0.0016(11) 0.0001(11) 0.0006(10)
    C8 0.0255(13) 0.0146(11) 0.0237(12) -0.0025(11) 0.0002(11) 0.0029(10)
    C9 0.0212(12) 0.0138(11) 0.0268(12) 0.0010(11) -0.0009(11) 0.0000(10)
    C10 0.0254(14) 0.0160(11) 0.0225(12) 0.0003(11) 0.0018(11) -0.0005(10)
    C11 0.0252(13) 0.0162(11) 0.0241(12) 0.0004(11) 0.0004(11) -0.0004(10)
    C12 0.0257(14) 0.0182(12) 0.0304(13) 0.0001(11) -0.0022(12) 0.0039(11)
    O71 0.0196(11) 0.0169(11) 0.0284(12) 0.0029(10) -0.0022(10) -0.0015(9)
    O72 0.039(5) 0.024(4) 0.028(4) 0.008(4) 0.011(4) 0.001(4)
    O10 0.0307(11) 0.0200(9) 0.0246(9) 0.0042(8) 0.0048(8) 0.0018(8)
    O11 0.0289(10) 0.0153(8) 0.0246(9) -0.0021(8) 0.0027(8) -0.0012(7)
    O12 0.0368(13) 0.0384(12) 0.0703(17) -0.0204(11) -0.0240(13) 0.0300(12)
    N1 0.0208(10) 0.0168(10) 0.0268(11) -0.0020(9) 0.0010(9) 0.0007(9)
    C13 0.0235(13) 0.0148(11) 0.0278(12) -0.0005(10) -0.0005(11) 0.0002(10)
    O13 0.0256(10) 0.0232(9) 0.0286(10) -0.0046(8) -0.0015(8) 0.0015(8)
    C14 0.0330(16) 0.0308(14) 0.0298(14) -0.0107(13) 0.0024(12) 0.0058(12)
    O1W 0.0484(14) 0.0261(10) 0.0365(12) -0.0066(11) 0.0090(11) -0.0014(9)
    O2W 0.0292(10) 0.0169(8) 0.0280(9) 0.0031(8) -0.0015(9) -0.0020(7)
_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
    C1 O1 . 1.394(3) ?
    C1 O5 . 1.426(3) ?
    C1 C2 . 1.525(3) ?
    C1 H1 . 1.0000 ?
    C2 O2 . 1.419(3) ?
    C2 C3 . 1.532(3) ?
    C2 H2 . 1.0000 ?
    C3 O3 . 1.414(3) ?
    C3 C4 . 1.518(4) ?
    C3 H3 . 1.0000 ?
    C4 O4 . 1.429(3) ?
    C4 C5 . 1.523(3) ?
    C4 H4 . 1.0000 ?
    C5 O5 . 1.432(3) ?
    C5 C6 . 1.516(4) ?
    C5 H5 . 1.0000 ?
    C6 O6 . 1.425(3) ?
    C6 H61 . 0.9900 ?
    C6 H62 . 0.9900 ?
    O1 C9 . 1.434(3) ?
    O2 H2O . 0.8500 ?
    O3 H3O . 0.8500 ?
    O4 H4O . 0.9338 ?
    O6 H6O . 0.8499 ?
    C7 O71 . 1.380(4) ?
    C7 O11 . 1.428(3) ?
    C7 O72 . 1.435(9) ?
    C7 C8 . 1.538(3) ?
    C7 H71 . 1.0000 ?
    C7 H72 . 1.0000 ?
    C8 N1 . 1.452(3) ?
    C8 C9 . 1.532(4) ?
    C8 H8 . 1.0000 ?
    C9 C10 . 1.528(4) ?
    C9 H9 . 1.0000 ?
    C10 O10 . 1.420(3) ?
    C10 C11 . 1.523(3) ?
    C10 H10 . 1.0000 ?
    C11 O11 . 1.437(3) ?
    C11 C12 . 1.514(4) ?
    C11 H11 . 1.0000 ?
    C12 O12 . 1.413(4) ?
    C12 H121 . 0.9900 ?
    C12 H122 . 0.9900 ?
    O71 H71O . 0.8594 ?
    O72 H72O . 0.8400 ?
    O10 H10O . 0.9571 ?
    O12 H12O . 0.8497 ?
    N1 C13 . 1.329(4) ?
    N1 H1N . 0.8800 ?
    C13 O13 . 1.246(4) ?
    C13 C14 . 1.504(4) ?
    C14 H141 . 0.9800 ?
    C14 H142 . 0.9800 ?
    C14 H143 . 0.9800 ?
    O1W H11W . 0.8500 ?
    O1W H12W . 0.8676 ?
    O2W H21W . 0.8963 ?
    O2W H22W . 0.8523 ?
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
    O1 C1 O5 . . 108.1(2) ?
    O1 C1 C2 . . 108.3(2) ?
    O5 C1 C2 . . 110.2(2) ?
    O1 C1 H1 . . 110.1 ?
    O5 C1 H1 . . 110.1 ?
    C2 C1 H1 . . 110.1 ?
    O2 C2 C1 . . 110.1(2) ?
    O2 C2 C3 . . 107.2(2) ?
    C1 C2 C3 . . 111.0(2) ?
    O2 C2 H2 . . 109.5 ?
    C1 C2 H2 . . 109.5 ?
    C3 C2 H2 . . 109.5 ?
    O3 C3 C4 . . 107.5(2) ?
    O3 C3 C2 . . 111.3(2) ?
    C4 C3 C2 . . 112.4(2) ?
    O3 C3 H3 . . 108.5 ?
    C4 C3 H3 . . 108.5 ?
    C2 C3 H3 . . 108.5 ?
    O4 C4 C3 . . 111.0(2) ?
    O4 C4 C5 . . 109.4(2) ?
    C3 C4 C5 . . 109.9(2) ?
    O4 C4 H4 . . 108.8 ?
    C3 C4 H4 . . 108.8 ?
    C5 C4 H4 . . 108.8 ?
    O5 C5 C6 . . 107.9(2) ?
    O5 C5 C4 . . 110.9(2) ?
    C6 C5 C4 . . 112.3(2) ?
    O5 C5 H5 . . 108.5 ?
    C6 C5 H5 . . 108.5 ?
    C4 C5 H5 . . 108.5 ?
    O6 C6 C5 . . 112.3(2) ?
    O6 C6 H61 . . 109.2 ?
    C5 C6 H61 . . 109.2 ?
    O6 C6 H62 . . 109.2 ?
    C5 C6 H62 . . 109.2 ?
    H61 C6 H62 . . 107.9 ?
    C1 O1 C9 . . 115.2(2) y
    C2 O2 H2O . . 114.2 ?
    C3 O3 H3O . . 110.2 ?
    C4 O4 H4O . . 105.5 ?
    C1 O5 C5 . . 111.8(2) ?
    C6 O6 H6O . . 113.0 ?
    O71 C7 O11 . . 111.5(2) ?
    O11 C7 O72 . . 109.2(4) ?
    O71 C7 C8 . . 107.1(2) ?
    O11 C7 C8 . . 109.4(2) ?
    O72 C7 C8 . . 115.9(4) ?
    O71 C7 H71 . . 109.6 ?
    O11 C7 H71 . . 109.6 ?
    C8 C7 H71 . . 109.6 ?
    O11 C7 H72 . . 107.4 ?
    O72 C7 H72 . . 107.2 ?
    C8 C7 H72 . . 107.4 ?
    N1 C8 C9 . . 112.7(2) ?
    N1 C8 C7 . . 109.2(2) ?
    C9 C8 C7 . . 108.5(2) ?
    N1 C8 H8 . . 108.8 ?
    C9 C8 H8 . . 108.8 ?
    C7 C8 H8 . . 108.8 ?
    O1 C9 C10 . . 110.9(2) ?
    O1 C9 C8 . . 110.3(2) ?
    C10 C9 C8 . . 107.2(2) ?
    O1 C9 H9 . . 109.5 ?
    C10 C9 H9 . . 109.5 ?
    C8 C9 H9 . . 109.5 ?
    O10 C10 C11 . . 107.8(2) ?
    O10 C10 C9 . . 112.3(2) ?
    C11 C10 C9 . . 108.6(2) ?
    O10 C10 H10 . . 109.4 ?
    C11 C10 H10 . . 109.4 ?
    C9 C10 H10 . . 109.4 ?
    O11 C11 C12 . . 108.7(2) ?
    O11 C11 C10 . . 108.7(2) ?
    C12 C11 C10 . . 114.8(2) ?
    O11 C11 H11 . . 108.2 ?
    C12 C11 H11 . . 108.2 ?
    C10 C11 H11 . . 108.2 ?
    O12 C12 C11 . . 110.9(2) ?
    O12 C12 H121 . . 109.5 ?
    C11 C12 H121 . . 109.5 ?
    O12 C12 H122 . . 109.5 ?
    C11 C12 H122 . . 109.5 ?
    H121 C12 H122 . . 108.0 ?
    C7 O71 H71O . . 113.3 ?
    C7 O72 H72O . . 109.5 ?
    C10 O10 H10O . . 110.6 ?
    C7 O11 C11 . . 113.28(19) ?
    C12 O12 H12O . . 115.9 ?
    C13 N1 C8 . . 123.4(2) ?
    C13 N1 H1N . . 118.3 ?
    C8 N1 H1N . . 118.3 ?
    O13 C13 N1 . . 123.6(3) ?
    O13 C13 C14 . . 120.2(2) ?
    N1 C13 C14 . . 116.2(2) ?
    C13 C14 H141 . . 109.5 ?
    C13 C14 H142 . . 109.5 ?
    H141 C14 H142 . . 109.5 ?
    C13 C14 H143 . . 109.5 ?
    H141 C14 H143 . . 109.5 ?
    H142 C14 H143 . . 109.5 ?
    H11W O1W H12W . . 103.1 ?
    H21W O2W H22W . . 108.4 ?
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
    O1 C1 C2 O2 . . . . -69.5(3) ?
    O5 C1 C2 O2 . . . . 172.4(2) ?
    O1 C1 C2 C3 . . . . 171.9(2) ?
    O5 C1 C2 C3 . . . . 53.9(3) ?
    O2 C2 C3 O3 . . . . 70.7(3) ?
    C1 C2 C3 O3 . . . . -169.0(2) ?
    O2 C2 C3 C4 . . . . -168.6(2) ?
    C1 C2 C3 C4 . . . . -48.3(3) ?
    O3 C3 C4 O4 . . . . 50.3(3) ?
    C2 C3 C4 O4 . . . . -72.6(3) ?
    O3 C3 C4 C5 . . . . 171.5(2) ?
    C2 C3 C4 C5 . . . . 48.6(3) ?
    O4 C4 C5 O5 . . . . 66.6(3) ?
    C3 C4 C5 O5 . . . . -55.5(3) ?
    O4 C4 C5 C6 . . . . -54.2(3) ?
    C3 C4 C5 C6 . . . . -176.4(2) ?
    O5 C5 C6 O6 . . . . 79.5(3) ?
    C4 C5 C6 O6 . . . . -157.9(2) ?
    O5 C1 O1 C9 . . . . -81.6(3) y
    C2 C1 O1 C9 . . . . 159.0(2) y
    O1 C1 O5 C5 . . . . 179.3(2) ?
    C2 C1 O5 C5 . . . . -62.6(3) ?
    C6 C5 O5 C1 . . . . -172.6(2) ?
    C4 C5 O5 C1 . . . . 64.0(3) ?
    O71 C7 C8 N1 . . . . 61.1(3) ?
    O11 C7 C8 N1 . . . . -178.0(2) ?
    O72 C7 C8 N1 . . . . -53.9(5) ?
    O71 C7 C8 C9 . . . . -62.2(3) ?
    O11 C7 C8 C9 . . . . 58.8(3) ?
    O72 C7 C8 C9 . . . . -177.2(5) ?
    C1 O1 C9 C10 . . . . 118.0(2) y
    C1 O1 C9 C8 . . . . -123.3(2) y
    N1 C8 C9 O1 . . . . 58.5(3) ?
    C7 C8 C9 O1 . . . . 179.6(2) ?
    N1 C8 C9 C10 . . . . 179.3(2) ?
    C7 C8 C9 C10 . . . . -59.5(3) ?
    O1 C9 C10 O10 . . . . -59.4(3) ?
    C8 C9 C10 O10 . . . . -179.9(2) ?
    O1 C9 C10 C11 . . . . -178.5(2) ?
    C8 C9 C10 C11 . . . . 61.0(3) ?
    O10 C10 C11 O11 . . . . 177.2(2) ?
    C9 C10 C11 O11 . . . . -60.9(3) ?
    O10 C10 C11 C12 . . . . 55.2(3) ?
    C9 C10 C11 C12 . . . . 177.1(2) ?
    O11 C11 C12 O12 . . . . -64.1(3) ?
    C10 C11 C12 O12 . . . . 57.9(3) ?
    O71 C7 O11 C11 . . . . 57.6(3) ?
    O72 C7 O11 C11 . . . . 171.4(5) ?
    C8 C7 O11 C11 . . . . -60.7(3) ?
    C12 C11 O11 C7 . . . . -172.7(2) ?
    C10 C11 O11 C7 . . . . 61.8(3) ?
    C9 C8 N1 C13 . . . . -125.0(3) ?
    C7 C8 N1 C13 . . . . 114.2(3) ?
    C8 N1 C13 O13 . . . . 2.1(4) ?
    C8 N1 C13 C14 . . . . -179.2(2) ?
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
    N1 H1N O2W 4_745 0.88 2.05 2.923(3) 169 y
    O2 H2O O12 4_655 0.85 1.80 2.642(3) 170 y
    O3 H3O O2W . 0.85 1.86 2.702(3) 169 y
    O4 H4O O13 4_655 0.93 1.95 2.803(3) 150 y
    O6 H6O O1W 3_556 0.85 1.79 2.624(3) 168 y
    O10 H10O O6 3_456 0.96 1.81 2.705(3) 154 y
    O1W H11W O10 3_456 0.85 1.85 2.696(3) 175 y
    O12 H12O O13 4_645 0.85 1.96 2.784(3) 162 y
    O1W H12W O4 . 0.87 1.90 2.759(3) 173 y
    O2W H21W O11 1_565 0.90 1.94 2.772(3) 154 y
    O2W H22W O6 2_664 0.85 1.91 2.757(3) 171 y
    O71 H71O O2 4_745 0.86 1.87 2.683(3) 159 y
    O72 H72O O1W 4_645 0.84 2.04 2.545(9) 119 y