##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
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data_global
_audit_creation_method     CRYSTALS_ver_14.11
_journal_date_recd_electronic     2010-09-17
_journal_date_accepted     2010-10-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     11
_journal_page_first     o2750
_journal_page_last     o2751
_journal_paper_category     QO
_journal_coeditor_code     HB5639
_publ_contact_author_name     'Anthony Other'
_publ_contact_author_address
;
 Chemistry Research Laboratory,
 Mansfield Road,
University of Oxford,
 Oxford, OX1 3TA, UK.
;
_publ_contact_author_email     'michela.simone@chem.ox.ac.uk'
_publ_contact_author_fax     '+44 1865 000000'
_publ_contact_author_phone     '+44 1865 000000'
_publ_section_title
;\
(3R,4R,5R)-5-(Acetamidomethyl)-N-benzyl-3,4-\
dihydroxytetrahydrofuran-3-carboxamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Simone, Michela I.' .
;
 Chemistry Research Laboratory, University of
 Oxford, Mansfield Road, Oxford, OX1 3TA, England
;
    'Edwards, Alison A.'
;
Present address:
Medway School of Pharmacy, Universities of Kent and Greenwich at Medway,
 Central Avenue, Chatham Maritime, Kent, ME4 4TB, England.
;
;
 Chemistry Research Laboratory, University of
 Oxford, Mansfield Road, Oxford, OX1 3TA, England
;
    'Cowley, Andrew R.' .
;
 Chemistry Research Laboratory, University of
 Oxford, Mansfield Road, Oxford, OX1 3TA, England
;
    'Fleet, George W. J.' .
;
 Chemistry  Research Laboratory, University of
 Oxford, Mansfield Road, Oxford, OX1 3TA, England
;
    'Watkin, David J.' .
;
 Chemistry  Research Laboratory, University of
 Oxford, Mansfield Road, Oxford, OX1 3TA, England
;
_chemical_name_systematic
;
(3R,4R,5R)-5-(Acetamidomethyl)-N-benzyl-
3,4-dihydroxytetrahydrofuran-3-carboxamide
;
_chemical_melting_point     ?
data_I
_chemical_name_systematic
;
 (3R,4R,5R)-5-(Acetamidomethyl)-N-benzyl-3,4-\
dihydroxytetrahydrofuran-3-carboxamide
;
_chemical_formula_moiety     'C15 H20 N2 O5'
_chemical_formula_sum     'C15 H20 N2 O5'
_chemical_formula_iupac     'C15 H20 N2 O5'
_chemical_formula_weight     308.33
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21 '
_symmetry_space_group_name_Hall     ?
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    'x+1/2,-y+1/2,-z'
    '-x,y+1/2,-z+1/2'
    '-x+1/2,-y,z+1/2'
_cell_length_a     5.4130(2)
_cell_length_b     8.5082(2)
_cell_length_c     32.6501(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1503.70(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6490
_cell_measurement_theta_min     2
_cell_measurement_theta_max     50
_cell_measurement_temperature     150
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.350
_exptl_crystal_size_mid     0.200
_exptl_crystal_size_min     0.040
_exptl_crystal_density_diffrn     1.362
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.859
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis RED; Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min     0.95
_exptl_absorpt_correction_T_max     0.97
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems open-flow
nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K.
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107.
The 9 missing reflections are all low-angle and in the penumbra of the beam
trap.
Their indices are
1 0 1
0 1 1
0 1 2
0 1 3
0 0 4
0 1 4
0 1 5
0 0 6
;
_diffrn_ambient_temperature     150
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Oxford Diffraction Gemini'
_diffrn_measurement_device     'Area'
_diffrn_measurement_method     ω
_diffrn_reflns_number     12797
_diffrn_reflns_av_R_equivalents     0.038
_diffrn_reflns_theta_min     5.373
_diffrn_reflns_theta_max     54.307
_diffrn_reflns_theta_full     54.307
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     34
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
;
_reflns_number_total     1805
_reflns_number_gt     1371
_reflns_threshold_expression     I>2.0σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0470
_refine_ls_R_factor_gt     0.0329
_refine_ls_wR_factor_all     0.0614
_refine_ls_wR_factor_gt     0.0601
_refine_ls_wR_factor_ref     0.0614
_refine_ls_goodness_of_fit_ref     0.9939
_refine_ls_number_reflns     1796
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
 Method= Modified Sheldrick
 w=1/[σ²(F²) + ( 0.10P)² + 0.00P]
 ,where P=(max(Fo²,0) + 2Fc²)/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.0002818
_refine_ls_shift/su_mean     0.0000437
_refine_diff_density_max     0.21
_refine_diff_density_min     -0.28
_refine_ls_extinction_method     'None'
_refine_ls_abs_structure_details     'Flack (1983), 681 Friedel pairs'
_refine_ls_abs_structure_Flack     0.0(3)
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0181 0.0091 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    N 0.0311 0.0180 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 0.0492 0.0322 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Gemini (Oxford Diffraction, 2006)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction, 2002)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2002)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement     'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics     'CAMERON (Watkin et al., 1996)'
_computing_publication_material     'CRYSTALS (Betteridge et al., 2003)'
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.5384(3) 0.54901(19) 0.24407(4) 0.0310 Uani 1.0000 . .
    C C2 0.5370(4) 0.5114(3) 0.28721(7) 0.0285 Uani 1.0000 . .
    C C3 0.2641(4) 0.5070(3) 0.29786(7) 0.0260 Uani 1.0000 . .
    C C4 0.1541(4) 0.4286(3) 0.25891(7) 0.0254 Uani 1.0000 . .
    C C5 0.3580(4) 0.4433(3) 0.22659(7) 0.0292 Uani 1.0000 . .
    O O6 0.1751(3) 0.6640(2) 0.30274(4) 0.0326 Uani 1.0000 . .
    O O7 0.0770(3) 0.27045(18) 0.26442(4) 0.0315 Uani 1.0000 . .
    C C8 0.2035(5) 0.4123(4) 0.33591(8) 0.0282 Uani 1.0000 . .
    O O9 0.3097(3) 0.2865(2) 0.34244(5) 0.0385 Uani 1.0000 . .
    N N10 0.0228(4) 0.4687(2) 0.35927(6) 0.0333 Uani 1.0000 . .
    C C11 -0.0761(5) 0.3862(3) 0.39501(7) 0.0386 Uani 1.0000 . .
    C C12 0.0572(5) 0.4266(4) 0.43394(8) 0.0357 Uani 1.0000 . .
    C C13 0.2683(6) 0.3472(4) 0.44544(9) 0.0475 Uani 1.0000 . .
    C C14 0.3884(6) 0.3856(4) 0.48131(11) 0.0609 Uani 1.0000 . .
    C C15 0.3030(7) 0.5041(5) 0.50564(9) 0.0650 Uani 1.0000 . .
    C C16 0.0949(7) 0.5856(4) 0.49430(9) 0.0609 Uani 1.0000 . .
    C C17 -0.0278(5) 0.5475(4) 0.45838(8) 0.0465 Uani 1.0000 . .
    C C18 0.2707(4) 0.5031(3) 0.18519(7) 0.0335 Uani 1.0000 . .
    N N19 0.4531(4) 0.4865(2) 0.15327(6) 0.0334 Uani 1.0000 . .
    C C20 0.4739(5) 0.3543(4) 0.13069(8) 0.0327 Uani 1.0000 . .
    O O21 0.3280(4) 0.2440(2) 0.13419(5) 0.0418 Uani 1.0000 . .
    C C22 0.6860(5) 0.3518(3) 0.10127(8) 0.0482 Uani 1.0000 . .
    H H61 0.1223 0.6945 0.2814 0.0479 Uiso 1.0000 . .
    H H71 0.1969 0.2186 0.2694 0.0465 Uiso 1.0000 . .
    H H101 -0.0317 0.5582 0.3538 0.0384 Uiso 1.0000 . .
    H H191 0.5586 0.5638 0.1497 0.0387 Uiso 1.0000 . .
    H H22 0.6302 0.5904 0.3029 0.0333 Uiso 1.0000 . .
    H H21 0.6124 0.4078 0.2913 0.0332 Uiso 1.0000 . .
    H H41 0.0066 0.4876 0.2499 0.0266 Uiso 1.0000 . .
    H H51 0.4304 0.3372 0.2225 0.0326 Uiso 1.0000 . .
    H H111 -0.2474 0.4142 0.3983 0.0447 Uiso 1.0000 . .
    H H112 -0.0631 0.2706 0.3888 0.0441 Uiso 1.0000 . .
    H H131 0.3326 0.2659 0.4287 0.0566 Uiso 1.0000 . .
    H H141 0.5300 0.3272 0.4883 0.0728 Uiso 1.0000 . .
    H H151 0.3864 0.5282 0.5307 0.0784 Uiso 1.0000 . .
    H H161 0.0278 0.6652 0.5111 0.0716 Uiso 1.0000 . .
    H H171 -0.1695 0.6031 0.4505 0.0557 Uiso 1.0000 . .
    H H181 0.2260 0.6167 0.1869 0.0395 Uiso 1.0000 . .
    H H182 0.1239 0.4446 0.1778 0.0396 Uiso 1.0000 . .
    H H223 0.6719 0.2678 0.0820 0.0701 Uiso 1.0000 . .
    H H222 0.8402 0.3475 0.1150 0.0711 Uiso 1.0000 . .
    H H221 0.6889 0.4446 0.0854 0.0713 Uiso 1.0000 . .
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 C2 . . 1.444(2) no
    O1 C5 . . 1.445(3) no
    C2 C3 . . 1.518(3) no
    C2 H22 . . 0.983 no
    C2 H21 . . 0.981 no
    C3 C4 . . 1.555(3) no
    C3 O6 . . 1.429(3) no
    C3 C8 . . 1.517(3) no
    C4 C5 . . 1.532(3) no
    C4 O7 . . 1.420(2) no
    C4 H41 . . 0.988 no
    C5 C18 . . 1.520(3) no
    C5 H51 . . 0.993 no
    O6 H61 . . 0.796 no
    O7 H71 . . 0.801 no
    C8 O9 . . 1.234(3) no
    C8 N10 . . 1.330(3) no
    N10 C11 . . 1.463(3) no
    N10 H101 . . 0.836 no
    C11 C12 . . 1.501(3) no
    C11 H111 . . 0.963 no
    C11 H112 . . 1.007 no
    C12 C13 . . 1.379(3) no
    C12 C17 . . 1.381(4) no
    C13 C14 . . 1.379(4) no
    C13 H131 . . 0.948 no
    C14 C15 . . 1.364(4) no
    C14 H141 . . 0.941 no
    C15 C16 . . 1.373(4) no
    C15 H151 . . 0.956 no
    C16 C17 . . 1.386(3) no
    C16 H161 . . 0.945 no
    C17 H171 . . 0.937 no
    C18 N19 . . 1.443(3) no
    C18 H181 . . 0.998 no
    C18 H182 . . 0.968 no
    N19 C20 . . 1.350(3) no
    N19 H191 . . 0.879 no
    C20 O21 . . 1.232(3) no
    C20 C22 . . 1.497(3) no
    C22 H223 . . 0.956 no
    C22 H222 . . 0.947 no
    C22 H221 . . 0.945 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
    C2 O1 C5 . . . 104.10(17) no
    O1 C2 C3 . . . 103.53(17) no
    O1 C2 H22 . . . 110.7 no
    C3 C2 H22 . . . 113.4 no
    O1 C2 H21 . . . 109.3 no
    C3 C2 H21 . . . 110.6 no
    H22 C2 H21 . . . 109.2 no
    C2 C3 C4 . . . 101.29(19) no
    C2 C3 O6 . . . 109.3(2) no
    C4 C3 O6 . . . 111.3(2) no
    C2 C3 C8 . . . 114.3(2) no
    C4 C3 C8 . . . 111.0(2) no
    O6 C3 C8 . . . 109.4(2) no
    C3 C4 C5 . . . 104.63(19) no
    C3 C4 O7 . . . 114.56(19) no
    C5 C4 O7 . . . 112.09(19) no
    C3 C4 H41 . . . 109.5 no
    C5 C4 H41 . . . 109.7 no
    O7 C4 H41 . . . 106.4 no
    C4 C5 O1 . . . 105.40(17) no
    C4 C5 C18 . . . 114.6(2) no
    O1 C5 C18 . . . 110.66(19) no
    C4 C5 H51 . . . 107.7 no
    O1 C5 H51 . . . 110.6 no
    C18 C5 H51 . . . 107.9 no
    C3 O6 H61 . . . 109.1 no
    C4 O7 H71 . . . 108.0 no
    C3 C8 O9 . . . 120.1(2) no
    C3 C8 N10 . . . 115.9(3) no
    O9 C8 N10 . . . 123.8(2) no
    C8 N10 C11 . . . 123.6(2) no
    C8 N10 H101 . . . 117.8 no
    C11 N10 H101 . . . 118.5 no
    N10 C11 C12 . . . 112.9(2) no
    N10 C11 H111 . . . 108.9 no
    C12 C11 H111 . . . 108.1 no
    N10 C11 H112 . . . 106.4 no
    C12 C11 H112 . . . 111.2 no
    H111 C11 H112 . . . 109.4 no
    C11 C12 C13 . . . 121.1(3) no
    C11 C12 C17 . . . 120.0(3) no
    C13 C12 C17 . . . 118.9(3) no
    C12 C13 C14 . . . 120.4(3) no
    C12 C13 H131 . . . 120.3 no
    C14 C13 H131 . . . 119.3 no
    C13 C14 C15 . . . 120.7(3) no
    C13 C14 H141 . . . 117.6 no
    C15 C14 H141 . . . 121.7 no
    C14 C15 C16 . . . 119.6(3) no
    C14 C15 H151 . . . 119.8 no
    C16 C15 H151 . . . 120.6 no
    C15 C16 C17 . . . 120.2(3) no
    C15 C16 H161 . . . 121.4 no
    C17 C16 H161 . . . 118.3 no
    C16 C17 C12 . . . 120.2(3) no
    C16 C17 H171 . . . 120.5 no
    C12 C17 H171 . . . 119.3 no
    C5 C18 N19 . . . 113.39(19) no
    C5 C18 H181 . . . 110.5 no
    N19 C18 H181 . . . 107.5 no
    C5 C18 H182 . . . 107.8 no
    N19 C18 H182 . . . 109.3 no
    H181 C18 H182 . . . 108.2 no
    C18 N19 C20 . . . 122.2(2) no
    C18 N19 H191 . . . 117.8 no
    C20 N19 H191 . . . 119.9 no
    N19 C20 O21 . . . 122.1(2) no
    N19 C20 C22 . . . 115.2(3) no
    O21 C20 C22 . . . 122.7(3) no
    C20 C22 H223 . . . 111.9 no
    C20 C22 H222 . . . 111.9 no
    H223 C22 H222 . . . 110.6 no
    C20 C22 H221 . . . 110.7 no
    H223 C22 H221 . . . 105.3 no
    H222 C22 H221 . . . 106.0 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
    O6 H61 O7 . . 3_555 0.80 1.95 2.737(4) 167 yes
    O7 H71 O1 . . 3_645 0.80 2.08 2.821(4) 154 yes
    N10 H101 O21 . . 3_555 0.84 2.29 3.023(4) 147 yes
    N19 H191 O9 . . 3_655 0.88 2.04 2.861(4) 155 yes
    C2 H22 O21 . . 3_655 0.98 2.45 3.322(4) 148 y
    C4 H41 O1 . . 1_455 0.99 2.59 3.520(4) 156 y
    C4 H41 O7 . . 3_555 0.99 2.49 3.257(4) 134 y
