##############################################################################
# #
# 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 #
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# #
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data_General
_audit_creation_method 'by CrystalStructure 4.0'
_journal_date_recd_electronic 2013-11-10
_journal_date_accepted 2013-11-13
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2013
_journal_volume 69
_journal_issue 12
_journal_page_first o1811
_journal_page_last o1811
_journal_paper_category QO
_journal_paper_doi 10.1107/S1600536813031140
_journal_coeditor_code IS5321
_publ_contact_author_name 'Prof Shigeru Ohba'
_publ_contact_author_address
;
Research and Education Center for Natural Sciences
Keio University
Hiyoshi 4-1-1, Kohoku-ku
Yokohama 223-8521
Japan
;
_publ_contact_author_email 'ohba@a3.keio.jp'
_publ_contact_author_fax '(81) 45 566 1314'
_publ_contact_author_phone '(81) 45 566 1308'
_publ_section_title
;
(-)-Benzyl 2,3-dideoxy-\b-D-erythro-hex-2-enopyranoside
;
loop_
_publ_author_name
_publ_author_address
'Ohba, Shigeru'
;
Research and Education Center for Natural Sciences
Keio University
Hiyoshi 4-1-1, Kohoku-ku
Yokohama 223-8521
Japan
;
'Okazaki, Hayato'
;
Department of Pharmaceutical Science
Keio University
Shibakoen 1-5-30, Minato-ku
Tokyo 105-8512
Japan
;
'Ueda, Yuji'
;
Department of Pharmaceutical Science
Keio University
Shibakoen 1-5-30, Minato-ku
Tokyo 105-8512
Japan
;
'Hanaya, Kengo'
;
Department of Pharmaceutical Science
Keio University
Shibakoen 1-5-30, Minato-ku
Tokyo 105-8512
Japan
;
'Shoji, Mitsuru'
;
Department of Pharmaceutical Science
Keio University
Shibakoen 1-5-30, Minato-ku
Tokyo 105-8512
Japan
;
'Sugai, Takeshi'
;
Department of Pharmaceutical Science
Keio University
Shibakoen 1-5-30, Minato-ku
Tokyo 105-8512
Japan
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 971648'
_chemical_name_systematic
;
(-)-Benzyl 2,3-dideoxy-\b-D-erythro-hex-2-enopyranoside
;
_chemical_formula_moiety 'C13 H16 O4'
_chemical_formula_sum 'C13 H16 O4'
_chemical_formula_weight 236.26
_chemical_melting_point_gt 353
_chemical_melting_point_lt 354
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 1 21 1'
_symmetry_space_group_name_Hall 'P 2yb'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 '+X,+Y,+Z'
2 '-X,1/2+Y,-Z'
_cell_length_a 19.500(9)
_cell_length_b 5.291(2)
_cell_length_c 6.0809(15)
_cell_angle_alpha 90.0000
_cell_angle_beta 94.27(3)
_cell_angle_gamma 90.0000
_cell_volume 625.7(4)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 25
_cell_measurement_theta_min 10.07
_cell_measurement_theta_max 12.54
_cell_measurement_temperature 292
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.60
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.254
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 252.00
_exptl_absorpt_coefficient_mu 0.093
_exptl_absorpt_correction_type none
_exptl_special_details
;
Spectroscopic data: IR \n max: 3292, 2937, 2872, 1377, 1325,
1176, 1144, 1122, 1051, 970, 951, 876, 787, 744, 696 cm^-1^; ^1^H NMR
(CDCl~3~): \d = 7.26--7.40 (m, 5H), 6.14 (ddd, J = 1.3, 4.6, 10.0 Hz,
1H), 5.89 (ddd, J = 1.0, 1.1, 10.0 Hz, 1H), 5.18 (ddd, J = 1.1,
1.3, 1.5 Hz, 1H), 4.92 (d, J = 11.8 Hz, 1H), 4.70 (d, J = 11.8
Hz, 1H), 4.02--4.09 (m, 1H), 3.97 (ddd, J = 5.9, 6.7, 12.0 Hz, 1H),
3.88 (ddd, J = 4.3, 7.3, 12.0 Hz, 1H), 3.79 (ddd, J = 3.1, 4.3,
6.7 Hz, 1H), 2.21 (dd, J = 5.9, 7.3 Hz, 1H), 1.97 (d, J = 10.6
Hz, 1H); ^13^C NMR (CDCl~3~): \d = 137.2, 130.9, 130.2, 128.4, 128.0, 127.9,
96.5, 75.1, 70.3, 62.9, 62.5.
;
_diffrn_ambient_temperature 292
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71069
_diffrn_radiation_source 'Rigaku rotating Mo anode'
_diffrn_radiation_monochromator 'graphite plate'
_diffrn_measurement_device_type 'Rigaku AFC-7R'
_diffrn_measurement_method \w-2\q
_diffrn_reflns_number 1713
_diffrn_reflns_av_R_equivalents 0.0344
_diffrn_reflns_theta_max 27.50
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 25
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_l_min -7
_diffrn_reflns_limit_l_max 7
_diffrn_standards_number 3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_% 0.763
_refine_special_details
;
Refinement was performed using all reflections. The weighted R-factor
(wR) and goodness of fit (S) are based on F^2^.
R-factor (gt) are based on F. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factor
(gt).
;
_reflns_number_total 1585
_reflns_number_gt 786
_reflns_threshold_expression F^2^>2\s(F^2^)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_gt 0.0563
_refine_ls_wR_factor_ref 0.2547
_refine_ls_goodness_of_fit_ref 1.044
_refine_ls_number_reflns 1579
_refine_ls_number_parameters 193
_refine_ls_number_restraints 33
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1473P)^2^+0.0601P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.001
_refine_diff_density_max 0.160
_refine_diff_density_min -0.170
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'see text'
_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
'O' 'O' 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
'C' 'C' 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
'H' 'H' 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
_computing_data_collection
;
WinAFC Diffractometer Control Software (Rigaku, 1999)
;
_computing_cell_refinement
;
WinAFC Diffractometer Control Software (Rigaku, 1999)
;
_computing_data_reduction 'CrystalStructure (Rigaku, 2010)'
_computing_structure_solution 'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'ORTEPII (Johnson, 1976)'
_computing_publication_material 'CrystalStructure (Rigaku, 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 0.3098(2) 0.1914(7) 0.7411(7) 0.0920(13) Uani d . 1.0 2 . .
O O2 0.4326(4) -0.2905(9) 0.9178(11) 0.152(3) Uani d . 1.0 2 . .
O O3 0.4652(2) 0.2679(10) 0.7637(8) 0.0988(14) Uani d . 1.0 2 . .
O O4A 0.2323(7) 0.485(3) 0.5340(18) 0.090(4) Uani d . 0.589(9) 2 . 1
O O4B 0.2402(8) 0.476(4) 0.638(2) 0.068(4) Uani d . 0.411(9) 2 . 2
C C5 0.3777(5) -0.1093(15) 0.9332(13) 0.116(3) Uani d . 1.0 2 . .
C C6 0.3606(3) 0.0062(11) 0.7108(10) 0.0822(15) Uani d . 1.0 2 . .
C C7 0.4216(3) 0.1300(14) 0.6082(9) 0.0837(16) Uani d . 1.0 2 . .
C C8 0.3960(3) 0.2985(17) 0.4253(8) 0.0933(19) Uani d . 1.0 2 . .
C C9 0.3317(3) 0.3656(15) 0.3939(10) 0.096(2) Uani d . 1.0 2 . .
C C10 0.2796(3) 0.2768(14) 0.5335(12) 0.0946(17) Uani d . 1.0 2 . .
C C11A 0.1683(5) 0.409(3) 0.605(3) 0.097(4) Uani d . 0.589(9) 2 . 1
C C11B 0.1941(7) 0.406(4) 0.797(4) 0.107(6) Uani d . 0.411(9) 2 . 2
C C12A 0.1400(7) 0.603(3) 0.754(2) 0.078(4) Uani d . 0.589(9) 2 . 1
C C12B 0.1432(11) 0.611(4) 0.826(4) 0.078(4) Uani d . 0.411(9) 2 . 2
C C13A 0.1743(7) 0.635(3) 0.960(2) 0.108(4) Uani d . 0.589(9) 2 . 1
C C13B 0.1432(12) 0.747(5) 1.019(4) 0.108(4) Uani d . 0.411(9) 2 . 2
C C14A 0.1520(9) 0.811(4) 1.107(3) 0.153(8) Uani d . 0.589(9) 2 . 1
C C14B 0.0960(16) 0.938(7) 1.038(5) 0.153(8) Uani d . 0.411(9) 2 . 2
C C15A 0.0936(10) 0.947(4) 1.041(3) 0.143(8) Uani d . 0.589(9) 2 . 1
C C15B 0.0485(15) 0.990(5) 0.867(4) 0.143(8) Uani d . 0.411(9) 2 . 2
C C16A 0.0592(8) 0.927(3) 0.837(3) 0.109(4) Uani d . 0.589(9) 2 . 1
C C16B 0.0481(10) 0.852(4) 0.674(3) 0.109(4) Uani d . 0.411(9) 2 . 2
C C17A 0.0842(9) 0.750(3) 0.696(3) 0.095(4) Uani d . 0.589(9) 2 . 1
C C17B 0.0940(15) 0.661(5) 0.659(5) 0.095(4) Uani d . 0.411(9) 2 . 2
H H2 0.4679 -0.2355 0.9822 0.1820 Uiso calc R 1.0 2 . .
H H3 0.4543 0.4176 0.7592 0.1185 Uiso calc R 1.0 2 . .
H H51 0.3919 0.0215 1.0387 0.1391 Uiso calc R 1.0 2 . .
H H52 0.3374 -0.1926 0.9836 0.1391 Uiso calc R 1.0 2 . .
H H6 0.3411 -0.1243 0.6103 0.0986 Uiso calc R 1.0 2 . .
H H7 0.4491 -0.0040 0.5463 0.1005 Uiso calc R 1.0 2 . .
H H8 0.4271 0.3589 0.3291 0.1120 Uiso calc R 1.0 2 . .
H H9 0.3188 0.4743 0.2779 0.1150 Uiso calc R 1.0 2 . .
H H10A 0.2558 0.1336 0.4596 0.1135 Uiso calc R 0.589(9) 2 . 1
H H10B 0.2496 0.1490 0.4601 0.1135 Uiso calc R 0.411(9) 2 . 2
H H11A 0.1737 0.2499 0.6832 0.1165 Uiso calc R 0.589(9) 2 . 1
H H11B 0.1361 0.3836 0.4779 0.1165 Uiso calc R 0.589(9) 2 . 1
H H11C 0.2197 0.3725 0.9365 0.1280 Uiso calc R 0.411(9) 2 . 2
H H11D 0.1701 0.2528 0.7494 0.1280 Uiso calc R 0.411(9) 2 . 2
H H13A 0.2127 0.5360 1.0006 0.1298 Uiso calc R 0.589(9) 2 . 1
H H13B 0.1750 0.7105 1.1365 0.1298 Uiso calc R 0.411(9) 2 . 2
H H14A 0.1753 0.8367 1.2442 0.1836 Uiso calc R 0.589(9) 2 . 1
H H14B 0.0965 1.0323 1.1672 0.1836 Uiso calc R 0.411(9) 2 . 2
H H15A 0.0767 1.0598 1.1409 0.1720 Uiso calc R 0.589(9) 2 . 1
H H15B 0.0164 1.1182 0.8812 0.1720 Uiso calc R 0.411(9) 2 . 2
H H16A 0.0211 1.0264 0.7962 0.1307 Uiso calc R 0.589(9) 2 . 1
H H16B 0.0168 0.8893 0.5555 0.1307 Uiso calc R 0.411(9) 2 . 2
H H17A 0.0621 0.7311 0.5564 0.1141 Uiso calc R 0.589(9) 2 . 1
H H17B 0.0920 0.5625 0.5324 0.1141 Uiso calc R 0.411(9) 2 . 2
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 0.089(3) 0.071(3) 0.121(3) 0.007(2) 0.040(3) -0.013(3)
O2 0.198(6) 0.072(3) 0.169(5) 0.023(4) -0.094(5) -0.033(3)
O3 0.083(3) 0.091(3) 0.117(3) 0.003(3) -0.029(2) -0.023(3)
O4A 0.079(6) 0.079(5) 0.111(8) 0.007(5) 0.009(7) 0.007(8)
O4B 0.051(6) 0.067(6) 0.087(9) 0.012(5) 0.010(7) 0.010(9)
C5 0.132(6) 0.088(5) 0.128(5) 0.001(5) 0.010(5) 0.019(5)
C6 0.089(4) 0.060(3) 0.097(4) 0.007(3) 0.003(3) -0.022(3)
C7 0.076(3) 0.093(4) 0.082(3) 0.020(3) 0.000(3) -0.032(3)
C8 0.080(4) 0.128(6) 0.073(3) 0.004(4) 0.012(3) -0.012(4)
C9 0.086(4) 0.118(6) 0.083(3) 0.005(4) -0.001(3) -0.008(4)
C10 0.067(3) 0.075(4) 0.141(5) 0.010(4) 0.005(4) -0.015(4)
C11A 0.057(5) 0.094(8) 0.141(9) -0.013(6) 0.016(6) -0.026(8)
C11B 0.060(8) 0.116(13) 0.146(15) 0.024(9) 0.023(9) 0.042(13)
C12A 0.062(4) 0.084(4) 0.088(10) 0.003(4) 0.002(6) 0.018(6)
C12B 0.062(4) 0.084(4) 0.088(10) 0.003(4) 0.002(6) 0.018(6)
C13A 0.107(9) 0.109(10) 0.106(8) 0.002(7) -0.009(7) 0.000(8)
C13B 0.107(9) 0.109(10) 0.106(8) 0.002(7) -0.009(7) 0.000(8)
C14A 0.159(14) 0.19(2) 0.107(10) -0.077(16) 0.007(9) -0.040(11)
C14B 0.159(14) 0.19(2) 0.107(10) -0.077(16) 0.007(9) -0.040(11)
C15A 0.169(16) 0.104(10) 0.171(17) 0.018(11) 0.109(13) 0.011(11)
C15B 0.169(16) 0.104(10) 0.171(17) 0.018(11) 0.109(13) 0.011(11)
C16A 0.096(7) 0.100(9) 0.134(11) 0.022(7) 0.031(8) -0.012(7)
C16B 0.096(7) 0.100(9) 0.134(11) 0.022(7) 0.031(8) -0.012(7)
C17A 0.076(7) 0.087(13) 0.121(7) 0.032(8) 0.004(6) 0.004(8)
C17B 0.076(7) 0.087(13) 0.121(7) 0.032(8) 0.004(6) 0.004(8)
_geom_special_details
;
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . . 1.416(8) no
O1 C10 . . 1.426(8) no
O2 C5 . . 1.445(11) no
O3 C7 . . 1.424(8) no
O4A C10 . . 1.438(17) no
O4A C11A . . 1.409(18) no
O4B C10 . . 1.477(19) no
O4B C11B . . 1.42(3) no
C5 C6 . . 1.499(10) no
C6 C7 . . 1.531(9) no
C7 C8 . . 1.483(9) no
C8 C9 . . 1.304(9) no
C9 C10 . . 1.449(9) no
C11A C12A . . 1.499(19) no
C11B C12B . . 1.49(3) no
C12A C13A . . 1.388(18) no
C12A C17A . . 1.36(3) no
C12B C13B . . 1.38(3) no
C12B C17B . . 1.37(4) no
C13A C14A . . 1.38(3) no
C13B C14B . . 1.38(4) no
C14A C15A . . 1.38(3) no
C14B C15B . . 1.37(4) no
C15A C16A . . 1.37(3) no
C15B C16B . . 1.39(3) no
C16A C17A . . 1.38(3) no
C16B C17B . . 1.36(4) no
O2 H2 . . 0.820 no
O3 H3 . . 0.820 no
C5 H51 . . 0.970 no
C5 H52 . . 0.970 no
C6 H6 . . 0.980 no
C7 H7 . . 0.980 no
C8 H8 . . 0.930 no
C9 H9 . . 0.930 no
C10 H10A . . 0.980 no
C10 H10B . . 0.980 no
C11A H11A . . 0.970 no
C11A H11B . . 0.970 no
C11B H11C . . 0.970 no
C11B H11D . . 0.970 no
C13A H13A . . 0.930 no
C13B H13B . . 0.930 no
C14A H14A . . 0.930 no
C14B H14B . . 0.930 no
C15A H15A . . 0.930 no
C15B H15B . . 0.930 no
C16A H16A . . 0.930 no
C16B H16B . . 0.930 no
C17A H17A . . 0.930 no
C17B H17B . . 0.930 no
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 O1 C10 . . . 110.5(5) no
C10 O4A C11A . . . 111.4(12) no
C10 O4B C11B . . . 118.8(16) no
O2 C5 C6 . . . 109.1(7) no
O1 C6 C5 . . . 106.0(6) no
O1 C6 C7 . . . 109.3(5) no
C5 C6 C7 . . . 114.5(6) no
O3 C7 C6 . . . 113.1(5) no
O3 C7 C8 . . . 109.9(6) no
C6 C7 C8 . . . 109.5(5) no
C7 C8 C9 . . . 122.7(6) no
C8 C9 C10 . . . 122.3(6) no
O1 C10 O4A . . . 117.6(7) no
O1 C10 O4B . . . 92.3(7) no
O1 C10 C9 . . . 111.1(5) no
O4A C10 C9 . . . 103.3(8) no
O4B C10 C9 . . . 115.4(9) no
O4A C11A C12A . . . 111.4(11) no
O4B C11B C12B . . . 110.7(18) no
C11A C12A C13A . . . 117.0(12) no
C11A C12A C17A . . . 123.9(12) no
C13A C12A C17A . . . 119.1(14) no
C11B C12B C13B . . . 121.7(19) no
C11B C12B C17B . . . 119(2) no
C13B C12B C17B . . . 119(2) no
C12A C13A C14A . . . 120.7(13) no
C12B C13B C14B . . . 120(2) no
C13A C14A C15A . . . 117.1(15) no
C13B C14B C15B . . . 120(3) no
C14A C15A C16A . . . 124.1(18) no
C14B C15B C16B . . . 120(3) no
C15A C16A C17A . . . 116.3(15) no
C15B C16B C17B . . . 119(2) no
C12A C17A C16A . . . 122.6(15) no
C12B C17B C16B . . . 122(3) no
C5 O2 H2 . . . 109.474 no
C7 O3 H3 . . . 109.475 no
O2 C5 H51 . . . 109.847 no
O2 C5 H52 . . . 109.853 no
C6 C5 H51 . . . 109.854 no
C6 C5 H52 . . . 109.864 no
H51 C5 H52 . . . 108.286 no
O1 C6 H6 . . . 108.978 no
C5 C6 H6 . . . 108.981 no
C7 C6 H6 . . . 108.989 no
O3 C7 H7 . . . 108.061 no
C6 C7 H7 . . . 108.071 no
C8 C7 H7 . . . 108.069 no
C7 C8 H8 . . . 118.624 no
C9 C8 H8 . . . 118.631 no
C8 C9 H9 . . . 118.863 no
C10 C9 H9 . . . 118.877 no
O1 C10 H10A . . . 108.127 no
O1 C10 H10B . . . 112.184 no
O4A C10 H10A . . . 108.127 no
O4B C10 H10B . . . 112.183 no
C9 C10 H10A . . . 108.128 no
C9 C10 H10B . . . 112.184 no
O4A C11A H11A . . . 109.342 no
O4A C11A H11B . . . 109.349 no
C12A C11A H11A . . . 109.342 no
C12A C11A H11B . . . 109.335 no
H11A C11A H11B . . . 107.980 no
O4B C11B H11C . . . 109.503 no
O4B C11B H11D . . . 109.498 no
C12B C11B H11C . . . 109.496 no
C12B C11B H11D . . . 109.495 no
H11C C11B H11D . . . 108.069 no
C12A C13A H13A . . . 119.650 no
C14A C13A H13A . . . 119.655 no
C12B C13B H13B . . . 120.088 no
C14B C13B H13B . . . 120.082 no
C13A C14A H14A . . . 121.432 no
C15A C14A H14A . . . 121.427 no
C13B C14B H14B . . . 119.853 no
C15B C14B H14B . . . 119.850 no
C14A C15A H15A . . . 117.945 no
C16A C15A H15A . . . 117.953 no
C14B C15B H15B . . . 120.031 no
C16B C15B H15B . . . 120.027 no
C15A C16A H16A . . . 121.839 no
C17A C16A H16A . . . 121.842 no
C15B C16B H16B . . . 120.433 no
C17B C16B H16B . . . 120.424 no
C12A C17A H17A . . . 118.712 no
C16A C17A H17A . . . 118.718 no
C12B C17B H17B . . . 119.115 no
C16B C17B H17B . . . 119.099 no
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
C6 O1 C10 O4A . . . . -173.3(5) no
C6 O1 C10 O4B . . . . -173.0(4) no
C6 O1 C10 C9 . . . . -54.6(6) no
C10 O1 C6 C5 . . . . -168.0(4) no
C10 O1 C6 C7 . . . . 68.1(5) no
C10 O4A C11A C12A . . . . 139.3(9) no
C11A O4A C10 O1 . . . . -74.9(11) no
C11A O4A C10 O4B . . . . -75.6(14) no
C11A O4A C10 C9 . . . . 162.3(9) no
C10 O4B C11B C12B . . . . -160.8(10) no
C11B O4B C10 O1 . . . . -58.0(13) no
C11B O4B C10 O4A . . . . 121(3) no
C11B O4B C10 C9 . . . . -172.7(11) no
O2 C5 C6 O1 . . . . -176.5(5) no
O2 C5 C6 C7 . . . . -56.0(7) no
O1 C6 C7 O3 . . . . 77.9(6) no
O1 C6 C7 C8 . . . . -45.0(6) no
C5 C6 C7 O3 . . . . -40.7(8) no
C5 C6 C7 C8 . . . . -163.7(5) no
O3 C7 C8 C9 . . . . -111.7(7) no
C6 C7 C8 C9 . . . . 13.0(9) no
C7 C8 C9 C10 . . . . -1.1(11) no
C8 C9 C10 O1 . . . . 20.8(10) no
C8 C9 C10 O4A . . . . 147.8(7) no
C8 C9 C10 O4B . . . . 124.1(7) no
O4A C11A C12A C13A . . . . -68.8(15) no
O4A C11A C12A C17A . . . . 109.9(13) no
O4B C11B C12B C13B . . . . -111.9(19) no
O4B C11B C12B C17B . . . . 70(2) no
C11A C12A C13A C14A . . . . 179.4(11) no
C11A C12A C17A C16A . . . . 179.8(12) no
C13A C12A C17A C16A . . . . -2(3) no
C17A C12A C13A C14A . . . . 1(2) no
C11B C12B C13B C14B . . . . 178.8(17) no
C11B C12B C17B C16B . . . . -177.4(19) no
C13B C12B C17B C16B . . . . 4(4) no
C17B C12B C13B C14B . . . . -3(4) no
C12A C13A C14A C15A . . . . 2(3) no
C12B C13B C14B C15B . . . . 1(4) no
C13A C14A C15A C16A . . . . -3(3) no
C13B C14B C15B C16B . . . . -1(5) no
C14A C15A C16A C17A . . . . 3(3) no
C14B C15B C16B C17B . . . . 2(4) no
C15A C16A C17A C12A . . . . 0(3) no
C15B C16B C17B C12B . . . . -4(4) no
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
O2 H2 O3 . . 2_647 0.82 1.95 2.692(8) 151 yes
O3 H3 O2 . . 1_565 0.82 1.89 2.614(8) 147 yes
_iucr_refine_instructions_details
;
TITL 3-O-benzyl-D-gulal
CELL 0.71069 19.49980 5.29090 6.08090 90.000 94.266 90.000
ZERR 2 0.00900 0.00200 0.00150 0.000 0.025 0.000
LATT -1
SYMM -X, .50+Y, -Z
SFAC O C H
UNIT 8 26 32
SHEL 5.094079 0.769564
L.S. 10
FMAP 2
PLAN -10
WPDB -2
HTAB
MERG 3
TEMP 19.0
ACTA
SIZE 0.600 0.400 0.200
DFIX 1.3800 0.0200 C13B C14B
DFIX 1.3800 0.0200 C14B C15B
DFIX 1.3800 0.0200 C15B C16B
DFIX 1.3800 0.0200 C16B C17B
EADP C13A C13B
EADP C14A C14B
EADP C15A C15B
EADP C16A C16B
EADP C17A C17B
EADP C12A C12B
DFIX 1.3800 0.0200 C12A C13A
DFIX 1.3800 0.0200 C13A C14A
DFIX 1.3800 0.0200 C14A C15A
DFIX 1.3800 0.0200 C15A C16A
DFIX 1.3800 0.0200 C16A C17A
DFIX 1.3800 0.0200 C12A C17A
DFIX 1.3800 0.0200 C12B C13B
DFIX 1.3800 0.0200 C12B C17B
FLAT 0.1000 C11A C12A C13A C14A C15A C16A C17A
FLAT 0.1000 C11B C12B C13B C14B C15B C16B C17B
DANG 2.39 0.0400 C17A C13A
DANG 2.39 0.0400 C12A C14A
DANG 2.39 0.0400 C13A C15A
DANG 2.39 0.0400 C14A C16A
DANG 2.39 0.0400 C15A C17A
DANG 2.39 0.0400 C16A C12A
DANG 2.39 0.0400 C17B C13B
DANG 2.39 0.0400 C14B C16B
DANG 2.39 0.0400 C15B C17B
DANG 2.39 0.0400 C16B C12B
DANG 2.39 0.0400 C12B C14B
DANG 2.39 0.0400 C13B C15B
WGHT 0.147300 0.060100
FVAR 2.20369 0.58900
PART 0
O1 1 0.309799 0.191406 0.741138 11.00000 0.08867 0.07084 =
0.12112 -0.01348 0.03973 0.00658
O2 1 0.432575 -0.290525 0.917803 11.00000 0.19781 0.07188 =
0.16923 -0.03292 -0.09422 0.02302
AFIX 147
H2 3 0.467903 -0.235494 0.982162 11.00000 -1.20000
AFIX 0
O3 1 0.465182 0.267874 0.763678 11.00000 0.08295 0.09086 =
0.11708 -0.02288 -0.02864 0.00278
AFIX 147
H3 3 0.454327 0.417619 0.759218 11.00000 -1.20000
AFIX 0
PART 1
O4A 1 0.232305 0.485171 0.533948 21.00000 0.07892 0.07945 =
0.11141 0.00736 0.00877 0.00693
PART 2
O4B 1 0.240252 0.476485 0.637859 -21.00000 0.05120 0.06658 =
0.08694 0.01033 0.00984 0.01217
PART 0
C5 2 0.377685 -0.109247 0.933202 11.00000 0.13192 0.08762 =
0.12830 0.01860 0.00959 0.00073
AFIX 23
H51 3 0.391898 0.021515 1.038744 11.00000 -1.20000
H52 3 0.337406 -0.192603 0.983550 11.00000 -1.20000
AFIX 0
C6 2 0.360628 0.006230 0.710771 11.00000 0.08880 0.05985 =
0.09729 -0.02192 0.00325 0.00662
AFIX 13
H6 3 0.341084 -0.124249 0.610307 11.00000 -1.20000
AFIX 0
C7 2 0.421643 0.130000 0.608191 11.00000 0.07569 0.09267 =
0.08191 -0.03185 -0.00040 0.01960
AFIX 13
H7 3 0.449077 -0.003974 0.546268 11.00000 -1.20000
AFIX 0
C8 2 0.395994 0.298520 0.425345 11.00000 0.08029 0.12769 =
0.07294 -0.01181 0.01211 0.00386
AFIX 43
H8 3 0.427082 0.358862 0.329078 11.00000 -1.20000
AFIX 0
C9 2 0.331675 0.365636 0.393893 11.00000 0.08560 0.11751 =
0.08325 -0.00808 -0.00119 0.00477
AFIX 43
H9 3 0.318761 0.474256 0.277885 11.00000 -1.20000
AFIX 0
C10 2 0.279627 0.276816 0.533463 11.00000 0.06680 0.07502 =
0.14150 -0.01492 0.00471 0.00963
PART 1
AFIX 13
H10A 3 0.255800 0.133641 0.459603 21.00000 -1.20000
AFIX 13
PART 2
H10B 3 0.249617 0.148971 0.460053 -21.00000 -1.20000
AFIX 0
PART 1
C11A 2 0.168316 0.409360 0.605200 21.00000 0.05716 0.09438 =
0.14105 -0.02629 0.01570 -0.01308
AFIX 23
H11A 3 0.173736 0.249861 0.683210 21.00000 -1.20000
H11B 3 0.136051 0.383629 0.477928 21.00000 -1.20000
AFIX 0
C12A 2 0.140004 0.603034 0.753948 21.00000 0.06184 0.08427 =
0.08813 0.01803 0.00200 0.00251
C13A 2 0.174299 0.634529 0.960397 21.00000 0.10680 0.10896 =
0.10613 -0.00005 -0.00939 0.00215
AFIX 43
H13A 3 0.212690 0.535965 1.000594 21.00000 -1.20000
AFIX 0
C14A 2 0.151989 0.810927 1.106972 21.00000 0.15934 0.19223 =
0.10710 -0.04005 0.00701 -0.07738
AFIX 43
H14A 3 0.175272 0.836730 1.244215 21.00000 -1.20000
AFIX 0
C15A 2 0.093618 0.947197 1.040763 21.00000 0.16917 0.10431 =
0.17090 0.01107 0.10902 0.01845
AFIX 43
H15A 3 0.076665 1.059795 1.140897 21.00000 -1.20000
AFIX 0
C16A 2 0.059242 0.926873 0.837362 21.00000 0.09643 0.09985 =
0.13388 -0.01212 0.03124 0.02237
AFIX 43
H16A 3 0.021128 1.026438 0.796177 21.00000 -1.20000
AFIX 0
C17A 2 0.084234 0.750218 0.696235 21.00000 0.07622 0.08710 =
0.12146 0.00446 0.00445 0.03168
AFIX 43
H17A 3 0.062112 0.731076 0.556392 21.00000 -1.20000
AFIX 0
PART 2
C11B 2 0.194068 0.406359 0.796641 -21.00000 0.05963 0.11633 =
0.14638 0.04240 0.02323 0.02423
AFIX 23
H11C 3 0.219660 0.372540 0.936469 -21.00000 -1.20000
H11D 3 0.170110 0.252803 0.749391 -21.00000 -1.20000
AFIX 0
C12B 2 0.143239 0.610651 0.825808 -21.00000 0.06184 0.08427 =
0.08813 0.01803 0.00200 0.00251
C13B 2 0.143218 0.747339 1.019174 -21.00000 0.10680 0.10896 =
0.10613 -0.00005 -0.00939 0.00215
AFIX 43
H13B 3 0.174990 0.710538 1.136487 -21.00000 -1.20000
AFIX 0
C14B 2 0.096048 0.938252 1.037905 -21.00000 0.15934 0.19223 =
0.10710 -0.04005 0.00701 -0.07738
AFIX 43
H14B 3 0.096538 1.032330 1.167201 -21.00000 -1.20000
AFIX 0
C15B 2 0.048504 0.990153 0.867356 -21.00000 0.16917 0.10431 =
0.17090 0.01107 0.10902 0.01845
AFIX 43
H15B 3 0.016439 1.118202 0.881204 -21.00000 -1.20000
AFIX 0
C16B 2 0.048112 0.851886 0.673840 -21.00000 0.09643 0.09985 =
0.13388 -0.01212 0.03124 0.02237
AFIX 43
H16B 3 0.016758 0.889284 0.555554 -21.00000 -1.20000
AFIX 0
C17B 2 0.094005 0.661412 0.659105 -21.00000 0.07622 0.08710 =
0.12146 0.00446 0.00445 0.03168
AFIX 43
H17B 3 0.092023 0.562473 0.532382 -21.00000 -1.20000
PART 0
HKLF 4
REM 3-O-benzyl-D-gulal
REM R1 = 0.0563 for 786 Fo > 4sig(Fo) and 0.1318 for all 1579 data
REM 193 parameters refined using 33 restraints
END
WGHT 0.1333 0.0794
REM Highest difference peak 0.163, deepest hole -0.172, 1-sigma level 0.039
Q1 1 0.3685 -0.4862 0.8464 11.00000 0.05 0.16
Q2 1 0.3579 0.4299 0.7127 11.00000 0.05 0.13
Q3 1 0.5088 -0.1025 0.9158 11.00000 0.05 0.12
Q4 1 0.3384 -0.1920 0.7179 11.00000 0.05 0.12
Q5 1 0.3695 -0.5514 1.0614 11.00000 0.05 0.12
Q6 1 0.3693 -0.0602 0.6559 11.00000 0.05 0.12
Q7 1 0.3612 0.3526 0.8930 11.00000 0.05 0.11
Q8 1 0.2109 0.0931 0.5853 11.00000 0.05 0.11
Q9 1 0.5052 0.2276 0.5255 11.00000 0.05 0.11
Q10 1 0.3602 0.2247 0.3464 11.00000 0.05 0.11
;