data_2013179
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o174
_journal_page_last  o176
_publ_section_title
;
Dhurrin from Henriettella fascicularis
;
loop_
_publ_author_name
  "Calder\'on, Angela I."
  'Terreaux, Christian'
  'Gupta, Mahabir P.'
  'Hostettmann, Kurt'
  'Schenk, Kurt J.'
_chemical_name_common  'dhurrin'
_chemical_formula_moiety  'C14 H17 N O7 , 2H2 O'
_chemical_formula_sum  'C14 H21 N O9'
_chemical_formula_weight  347.32
_chemical_melting_point  409
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2'
_symmetry_space_group_name_Hall  'C 2y'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z'
_cell_length_a  16.055(4)
_cell_length_b  6.2858(17)
_cell_length_c  16.895(5)
_cell_angle_alpha  90
_cell_angle_beta  109.299(5)
_cell_angle_gamma  90
_cell_volume  1609.2(8)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.434
_diffrn_ambient_temperature  293(2)
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 0.21942(14) 1.0239(4) 0.23026(12) 0.0326(6) Uani d . 1 . . O
  O2 0.24078(14) 0.7259(4) 0.31082(12) 0.0314(6) Uani d . 1 . . O
  O3 0.24867(16) 0.5232(4) 0.46412(13) 0.0485(7) Uani d . 1 . . O
  H3O 0.2937 0.4864 0.5014 0.073 Uiso calc R 1 . . H
  O4 0.43406(15) 0.3770(4) 0.39617(14) 0.0418(6) Uani d . 1 . . O
  H4O 0.4225 0.3095 0.4328 0.063 Uiso calc R 1 . . H
  O5 0.50862(14) 0.7739(4) 0.36573(14) 0.0373(6) Uani d . 1 . . O
  H5O 0.5440 0.6783 0.3676 0.056 Uiso calc R 1 . . H
  O6 0.39185(16) 0.9918(4) 0.22364(14) 0.0443(7) Uani d . 1 . . O
  H6O 0.4433 0.9603 0.2304 0.066 Uiso calc R 1 . . H
  O7 0.1490(2) 0.8818(4) -0.15585(13) 0.0543(8) Uani d . 1 . . O
  H7O 0.1433 0.7564 -0.1700 0.081 Uiso calc R 1 . . H
  O1W 0.09012(18) 0.5805(5) 0.48741(17) 0.0553(8) Uani d D 1 . . O
  H11W 0.1353(11) 0.531(6) 0.482(2) 0.083 Uiso d D 1 . . H
  H12W 0.0472(13) 0.522(6) 0.4539(19) 0.083 Uiso d D 1 . . H
  O2W 0.6178(2) 0.4254(4) 0.3809(2) 0.0627(9) Uani d D 1 . . O
  H22W 0.581(2) 0.342(5) 0.386(3) 0.094 Uiso d D 1 . . H
  H21W 0.651(2) 0.362(5) 0.361(2) 0.094 Uiso d D 1 . . H
  N 0.0492(2) 1.3428(7) 0.18401(18) 0.0650(12) Uani d . 1 . . N
  C1 0.0847(3) 1.1895(7) 0.1784(2) 0.0419(11) Uani d . 1 . . C
  C2 0.1313(2) 0.9954(6) 0.17032(18) 0.0349(9) Uani d . 1 . . C
  H2 0.1033 0.8727 0.1870 0.042 Uiso calc R 1 . . H
  C3 0.1324(2) 0.9623(6) 0.08199(19) 0.0322(9) Uani d . 1 . . C
  C4 0.1117(2) 0.7675(6) 0.04304(19) 0.0390(10) Uani d . 1 . . C
  H4 0.0947 0.6561 0.0706 0.047 Uiso calc R 1 . . H
  C5 0.1158(2) 0.7355(6) -0.0371(2) 0.0433(10) Uani d . 1 . . C
  H5 0.1019 0.6036 -0.0631 0.052 Uiso calc R 1 . . H
  C6 0.1408(2) 0.9025(6) -0.0775(2) 0.0373(9) Uani d . 1 . . C
  C7 0.1607(2) 1.0987(6) -0.0396(2) 0.0409(10) Uani d . 1 . . C
  H7 0.1770 1.2107 -0.0673 0.049 Uiso calc R 1 . . H
  C8 0.1562(2) 1.1279(6) 0.0397(2) 0.0406(10) Uani d . 1 . . C
  H8 0.1693 1.2605 0.0652 0.049 Uiso calc R 1 . . H
  C1A 0.2688(2) 0.8345(6) 0.25021(18) 0.0293(9) Uani d . 1 . . C
  H1A 0.2592 0.7466 0.2001 0.035 Uiso calc R 1 . . H
  C2A 0.3651(2) 0.8951(6) 0.28808(18) 0.0279(8) Uani d . 1 . . C
  H2A 0.3718 0.9982 0.3333 0.034 Uiso calc R 1 . . H
  C3A 0.4209(2) 0.6991(5) 0.3236(2) 0.0283(9) Uani d . 1 . . C
  H3A 0.4220 0.6087 0.2767 0.034 Uiso calc R 1 . . H
  C4A 0.3843(2) 0.5705(5) 0.37996(19) 0.0280(8) Uani d . 1 . . C
  H4A 0.3924 0.6471 0.4325 0.034 Uiso calc R 1 . . H
  C5A 0.2868(2) 0.5256(5) 0.33529(18) 0.0289(8) Uani d . 1 . . C
  H5A 0.2805 0.4414 0.2848 0.035 Uiso calc R 1 . . H
  C6A 0.2417(2) 0.4098(6) 0.38847(19) 0.0383(9) Uani d . 1 . . C
  H6AB 0.1798 0.3903 0.3562 0.046 Uiso calc R 1 . . H
  H6AA 0.2680 0.2701 0.4028 0.046 Uiso calc R 1 . . H
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
  O1 0.0307(13) 0.0321(16) 0.0303(12) 0.0082(13) 0.0037(11) 0.0005(12)
  O2 0.0292(14) 0.0326(15) 0.0341(13) 0.0062(12) 0.0126(11) 0.0092(12)
  O3 0.0436(17) 0.071(2) 0.0347(14) 0.0104(16) 0.0177(12) 0.0063(15)
  O4 0.0417(16) 0.0355(16) 0.0517(16) 0.0114(14) 0.0201(13) 0.0152(13)
  O5 0.0239(14) 0.0395(17) 0.0435(14) 0.0010(12) 0.0043(12) -0.0033(13)
  O6 0.0397(16) 0.0499(18) 0.0506(15) 0.0076(15) 0.0246(13) 0.0198(13)
  O7 0.092(2) 0.0439(17) 0.0315(14) 0.0010(18) 0.0262(14) -0.0029(13)
  O1W 0.0359(16) 0.062(2) 0.067(2) -0.0001(16) 0.0158(15) -0.0186(16)
  O2W 0.058(2) 0.057(2) 0.087(2) 0.0142(16) 0.0419(18) 0.0159(18)
  N 0.063(3) 0.086(3) 0.049(2) 0.041(2) 0.0228(18) 0.010(2)
  C1 0.034(2) 0.063(3) 0.028(2) 0.017(2) 0.0102(17) 0.005(2)
  C2 0.028(2) 0.048(3) 0.0304(19) 0.002(2) 0.0118(16) 0.0065(17)
  C3 0.029(2) 0.038(2) 0.0264(19) 0.0020(17) 0.0051(16) -0.0005(17)
  C4 0.042(2) 0.038(3) 0.037(2) -0.003(2) 0.0133(18) 0.006(2)
  C5 0.058(3) 0.030(2) 0.040(2) -0.005(2) 0.0136(19) -0.0043(19)
  C6 0.041(2) 0.036(3) 0.032(2) 0.003(2) 0.0086(18) 0.002(2)
  C7 0.058(3) 0.036(3) 0.032(2) -0.005(2) 0.019(2) 0.0012(18)
  C8 0.051(3) 0.036(2) 0.034(2) -0.007(2) 0.0129(19) -0.0036(18)
  C1A 0.032(2) 0.036(3) 0.0206(18) 0.0034(18) 0.0101(16) -0.0005(16)
  C2A 0.029(2) 0.031(2) 0.0245(18) 0.0018(18) 0.0096(16) 0.0013(16)
  C3A 0.025(2) 0.030(2) 0.0289(18) -0.0005(17) 0.0085(15) -0.0053(17)
  C4A 0.031(2) 0.025(2) 0.0260(18) 0.0050(17) 0.0071(16) 0.0000(17)
  C5A 0.028(2) 0.031(2) 0.0270(18) 0.0036(19) 0.0081(15) 0.0027(17)
  C6A 0.028(2) 0.042(2) 0.041(2) 0.0004(19) 0.0062(18) 0.008(2)
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 C1A . 1.409(4) ?
  O1 C2 . 1.453(4) ?
  O2 C1A . 1.422(3) ?
  O2 C5A . 1.449(4) ?
  O3 C6A . 1.435(4) ?
  O3 H3O . 0.8200 ?
  O4 C4A . 1.431(4) ?
  O4 H4O . 0.8200 ?
  O5 C3A . 1.431(4) ?
  O5 H5O . 0.8200 ?
  O6 C2A . 1.431(3) ?
  O6 H6O . 0.8200 ?
  O7 C6 . 1.379(4) ?
  O7 H7O . 0.8200 ?
  O1W H11W . 0.822(5) ?
  O1W H12W . 0.820(5) ?
  O2W H22W . 0.821(5) ?
  O2W H21W . 0.823(5) ?
  N C1 . 1.139(5) ?
  C1 C2 . 1.462(5) ?
  C2 C3 . 1.512(4) ?
  C2 H2 . 0.9800 ?
  C3 C4 . 1.378(5) ?
  C3 C8 . 1.386(5) ?
  C4 C5 . 1.392(4) ?
  C4 H4 . 0.9300 ?
  C5 C6 . 1.382(5) ?
  C5 H5 . 0.9300 ?
  C6 C7 . 1.378(5) ?
  C7 C8 . 1.377(4) ?
  C7 H7 . 0.9300 ?
  C8 H8 . 0.9300 ?
  C1A C2A . 1.513(4) ?
  C1A H1A . 0.9800 ?
  C2A C3A . 1.525(5) ?
  C2A H2A . 0.9800 ?
  C3A C4A . 1.508(4) ?
  C3A H3A . 0.9800 ?
  C4A C5A . 1.523(4) ?
  C4A H4A . 0.9800 ?
  C5A C6A . 1.514(4) ?
  C5A H5A . 0.9800 ?
  C6A H6AB . 0.9700 ?
  C6A H6AA . 0.9700 ?