##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     CRYSTALS_ver_12.39
_journal_date_recd_electronic     2004-10-22
_journal_date_accepted     2004-11-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue     12
_journal_page_first     o2334
_journal_page_last     o2336
_journal_paper_category     EO
_publ_contact_author_name     'Christopher Harding'
_publ_contact_author_address
;
 Chemical Crystallography,
 Chemistry Research Laboratory,
 University of Oxford,
 Oxford OX1 3TA, England
;
_publ_contact_author_email     christopher.harding@seh.ox.ac.uk
_publ_contact_author_fax     '-'
_publ_contact_author_phone     '+44 7976 503930'
_publ_section_title
;
3-Azido-3-deoxy-2,2':5,6-di-O-isopropylidene-2-C-hydroxmethyl-D-
gulono-1,4-lactone
;
loop_
    _publ_author_name
    _publ_author_address
    'Christopher C. Harding'
;
Department of Chemical Crystallography
Chemical Research Laboratory
Oxford University
Mansfield Road
Oxford OX1 3TA
England
;
    'Howard Shallard-Brown'
;
Department of Chemical Crystallography
Chemical Research Laboratory
Oxford University
Mansfield Road
Oxford OX1 3TA
England
;
    'David J. Watkin'
;
Department of Chemical Crystallography
Chemical Research Laboratory
Oxford University
Mansfield Road
Oxford OX1 3TA
England
;
    'Raquel Soengas'
;
Department of Organic Chemistry
Chemical Research Laboratory
Oxford University
Mansfield Road
Oxford OX1 3TA
England
;
    'George W. J. Fleet'
;
Department of Organic Chemistry
Chemical Research Laboratory
Oxford University
Mansfield Road
Oxford OX1 3TA
England
;
data_4
_chemical_name_systematic
;
3-Azido-3-deoxy-2,2':5,6-di-O-isopropylidene-2-C-hydroxmethyl-D-
gulono-1,4-lactone
;
_chemical_formula_moiety     'C13 H19 N3 O6'
_chemical_formula_sum     'C13 H19 N3 O6'
_chemical_formula_iupac     'C13 H19 N3 O6'
_chemical_formula_weight     313.31
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21 '
_symmetry_space_group_name_Hall     '?'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,y+1/2,-z'
_cell_length_a     8.7755(2)
_cell_length_b     7.6452(2)
_cell_length_c     12.2232(3)
_cell_angle_alpha     90
_cell_angle_beta     106.9659(11)
_cell_angle_gamma     90
_cell_volume     784.37(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1734
_cell_measurement_theta_min     5
_cell_measurement_theta_max     27
_cell_measurement_temperature     120
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.326
_exptl_crystal_density_meas     ?
_exptl_crystal_F_000     332
_exptl_absorpt_coefficient_mu     0.106
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min     0.98
_exptl_absorpt_correction_T_max     0.99
_diffrn_ambient_temperature     120
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_method     ω
_diffrn_reflns_number     3320
_diffrn_reflns_av_R_equivalents     0.015
_diffrn_reflns_theta_min     5.232
_diffrn_reflns_theta_max     27.536
_diffrn_reflns_theta_full     25.058
_diffrn_measured_fraction_theta_max     0.961
_diffrn_measured_fraction_theta_full     0.979
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     1869
_reflns_number_gt     1655
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0518
_refine_ls_R_factor_gt     0.0448
_refine_ls_wR_factor_all     0.1085
_refine_ls_wR_factor_gt     0.1051
_refine_ls_wR_factor_ref     0.1085
_refine_ls_goodness_of_fit_ref     0.9324
_refine_ls_number_reflns     1866
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Method: SHELXL97 (Sheldrick, 1997);
w = 1/[σ²(f)+(0.0522p)²+0.571p], where p = [max(F₀²,0)+2Fc²]/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.000326
_refine_diff_density_max     0.65
_refine_diff_density_min     -0.42
_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 22'
_refine_ls_extinction_coef      30E1(5)
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1997--2001)'
_computing_cell_refinement     'DENZO/SCALEPACK'
_computing_data_reduction     'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'User-defined structure solution (reference?)'
_computing_structure_refinement     'CRYSTALS (Betteridge et al 2003)'
_computing_molecular_graphics     'CAMERON (Watkin et al 1996)'
_computing_publication_material     'CRYSTALS '
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    C1 0.8173(3) 0.1205(4) 0.8704(2) 0.0207 Uani 1.0000 . . C
    C2 0.8728(3) 0.0356(4) 0.9895(2) 0.0197 Uani 1.0000 . . C
    C3 0.7808(3) 0.1387(4) 1.0574(2) 0.0214 Uani 1.0000 . . C
    C4 0.8684(3) 0.1553(4) 1.1835(2) 0.0253 Uani 1.0000 . . C
    O5 0.8788(3) -0.0165(3) 1.22982(16) 0.0306 Uani 1.0000 . . O
    C6 0.8328(4) -0.0098(5) 1.3330(3) 0.0349 Uani 1.0000 . . C
    O7 0.7463(5) 0.1409(5) 1.3271(3) 0.0777 Uani 1.0000 . . O
    C8 0.7788(4) 0.2612(4) 1.2524(3) 0.0345 Uani 1.0000 . . C
    C9 0.9801(6) 0.0021(9) 1.4333(3) 0.0762 Uani 1.0000 . . C
    C10 0.7390(8) -0.1702(9) 1.3373(5) 0.0891 Uani 1.0000 . . C
    O11 0.7642(2) 0.3122(3) 1.00698(16) 0.0251 Uani 1.0000 . . O
    C12 0.7805(3) 0.3076(4) 0.8996(2) 0.0234 Uani 1.0000 . . C
    O13 0.7649(3) 0.4350(3) 0.84141(18) 0.0315 Uani 1.0000 . . O
    N14 0.8584(3) -0.1555(3) 0.9887(2) 0.0219 Uani 1.0000 . . N
    N15 0.7245(3) -0.2124(4) 0.9845(2) 0.0267 Uani 1.0000 . . N
    N16 0.6106(4) -0.2828(4) 0.9831(3) 0.0454 Uani 1.0000 . . N
    O17 0.6748(2) 0.0412(3) 0.80306(15) 0.0223 Uani 1.0000 . . O
    C18 0.6968(3) -0.0131(4) 0.6948(2) 0.0246 Uani 1.0000 . . C
    O19 0.8643(2) -0.0228(3) 0.71573(16) 0.0250 Uani 1.0000 . . O
    C20 0.9322(3) 0.1103(4) 0.7966(2) 0.0252 Uani 1.0000 . . C
    C21 0.6301(4) -0.1943(5) 0.6674(3) 0.0338 Uani 1.0000 . . C
    C22 0.6235(4) 0.1233(5) 0.6046(3) 0.0408 Uani 1.0000 . . C
    H21 0.9848 0.0640 1.0229 0.0240 Uiso 1.0000 . . H
    H31 0.6712 0.0884 1.0445 0.0251 Uiso 1.0000 . . H
    H41 0.9753 0.2039 1.1948 0.0304 Uiso 1.0000 . . H
    H81 0.8497 0.3528 1.2967 0.0438 Uiso 1.0000 . . H
    H82 0.6789 0.3123 1.2055 0.0432 Uiso 1.0000 . . H
    H91 0.9408 0.0093 1.5009 0.0912 Uiso 1.0000 . . H
    H92 1.0438 -0.1057 1.4370 0.0913 Uiso 1.0000 . . H
    H93 1.0444 0.1073 1.4251 0.0920 Uiso 1.0000 . . H
    H101 0.7105 -0.1659 1.4094 0.1170 Uiso 1.0000 . . H
    H102 0.8053 -0.2750 1.3328 0.1173 Uiso 1.0000 . . H
    H103 0.6413 -0.1563 1.2703 0.1167 Uiso 1.0000 . . H
    H201 1.0400 0.0778 0.8411 0.0321 Uiso 1.0000 . . H
    H202 0.9326 0.2218 0.7573 0.0317 Uiso 1.0000 . . H
    H211 0.6543 -0.2349 0.5979 0.0399 Uiso 1.0000 . . H
    H212 0.6785 -0.2742 0.7300 0.0403 Uiso 1.0000 . . H
    H213 0.5151 -0.1924 0.6528 0.0409 Uiso 1.0000 . . H
    H221 0.6405 0.1021 0.5300 0.0487 Uiso 1.0000 . . H
    H222 0.6603 0.2431 0.6279 0.0489 Uiso 1.0000 . . H
    H223 0.5076 0.1206 0.5922 0.0491 Uiso 1.0000 . . H
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
    C1 C2 . . 1.538(4) no
    C1 C12 . . 1.531(4) no
    C1 O17 . . 1.417(3) no
    C1 C20 . . 1.539(3) no
    C2 C3 . . 1.533(4) no
    C2 N14 . . 1.466(4) no
    C2 H21 . . 0.973 no
    C3 C4 . . 1.514(4) no
    C3 O11 . . 1.452(3) no
    C3 H31 . . 1.005 no
    C4 O5 . . 1.423(4) no
    C4 C8 . . 1.538(4) no
    C4 H41 . . 0.981 no
    O5 C6 . . 1.433(3) yes
    C6 O7 . . 1.370(5) yes
    C6 C9 . . 1.503(6) yes
    C6 C10 . . 1.486(7) yes
    O7 C8 . . 1.384(4) yes
    C8 H81 . . 0.987 no
    C8 H82 . . 0.979 no
    C9 H91 . . 0.985 no
    C9 H92 . . 0.989 no
    C9 H93 . . 1.004 no
    C10 H101 . . 0.984 no
    C10 H102 . . 1.001 no
    C10 H103 . . 1.004 no
    O11 C12 . . 1.362(3) no
    C12 O13 . . 1.190(4) no
    N14 N15 . . 1.240(3) no
    N15 N16 . . 1.131(4) no
    O17 C18 . . 1.452(3) no
    C18 O19 . . 1.419(3) no
    C18 C21 . . 1.504(5) no
    C18 C22 . . 1.518(4) no
    O19 C20 . . 1.422(3) no
    C20 H201 . . 0.976 no
    C20 H202 . . 0.979 no
    C21 H211 . . 0.984 no
    C21 H212 . . 0.974 no
    C21 H213 . . 0.973 no
    C22 H221 . . 0.980 no
    C22 H222 . . 0.985 no
    C22 H223 . . 0.984 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 C1 C12 . . . 101.8(2) no
    C2 C1 O17 . . . 110.6(2) no
    C12 C1 O17 . . . 109.0(2) no
    C2 C1 C20 . . . 116.9(2) no
    C12 C1 C20 . . . 113.8(2) no
    O17 C1 C20 . . . 104.8(2) no
    C1 C2 C3 . . . 102.9(2) no
    C1 C2 N14 . . . 114.3(2) no
    C3 C2 N14 . . . 117.3(2) no
    C1 C2 H21 . . . 107.763 no
    C3 C2 H21 . . . 106.585 no
    N14 C2 H21 . . . 107.444 no
    C2 C3 C4 . . . 113.8(2) no
    C2 C3 O11 . . . 104.1(2) no
    C4 C3 O11 . . . 108.3(2) no
    C2 C3 H31 . . . 110.457 no
    C4 C3 H31 . . . 111.708 no
    O11 C3 H31 . . . 108.048 no
    C3 C4 O5 . . . 106.4(2) no
    C3 C4 C8 . . . 114.4(2) no
    O5 C4 C8 . . . 104.6(2) no
    C3 C4 H41 . . . 110.832 no
    O5 C4 H41 . . . 110.245 no
    C8 C4 H41 . . . 110.109 no
    C4 O5 C6 . . . 108.4(2) no
    O5 C6 O7 . . . 106.2(3) no
    O5 C6 C9 . . . 108.9(3) no
    O7 C6 C9 . . . 108.9(4) no
    O5 C6 C10 . . . 107.6(3) no
    O7 C6 C10 . . . 113.0(4) no
    C9 C6 C10 . . . 112.0(4) no
    C6 O7 C8 . . . 112.1(2) no
    C4 C8 O7 . . . 104.4(3) no
    C4 C8 H81 . . . 109.437 no
    O7 C8 H81 . . . 109.119 no
    C4 C8 H82 . . . 113.777 no
    O7 C8 H82 . . . 109.278 no
    H81 C8 H82 . . . 110.606 no
    C6 C9 H91 . . . 105.028 no
    C6 C9 H92 . . . 109.043 no
    H91 C9 H92 . . . 109.895 no
    C6 C9 H93 . . . 109.937 no
    H91 C9 H93 . . . 112.584 no
    H92 C9 H93 . . . 110.192 no
    C6 C10 H101 . . . 107.044 no
    C6 C10 H102 . . . 108.749 no
    H101 C10 H102 . . . 112.303 no
    C6 C10 H103 . . . 103.516 no
    H101 C10 H103 . . . 110.346 no
    H102 C10 H103 . . . 114.253 no
    C3 O11 C12 . . . 111.1(2) no
    C1 C12 O11 . . . 109.7(2) no
    C1 C12 O13 . . . 128.4(2) no
    O11 C12 O13 . . . 121.9(3) no
    C2 N14 N15 . . . 115.4(2) no
    N14 N15 N16 . . . 172.0(3) no
    C1 O17 C18 . . . 108.8(2) no
    O17 C18 O19 . . . 104.9(2) no
    O17 C18 C21 . . . 108.6(2) no
    O19 C18 C21 . . . 107.9(2) no
    O17 C18 C22 . . . 109.0(2) no
    O19 C18 C22 . . . 111.4(2) no
    C21 C18 C22 . . . 114.6(3) no
    C18 O19 C20 . . . 106.8(2) no
    C1 C20 O19 . . . 103.3(2) no
    C1 C20 H201 . . . 112.385 no
    O19 C20 H201 . . . 110.314 no
    C1 C20 H202 . . . 109.886 no
    O19 C20 H202 . . . 110.026 no
    H201 C20 H202 . . . 110.659 no
    C18 C21 H211 . . . 108.339 no
    C18 C21 H212 . . . 110.490 no
    H211 C21 H212 . . . 109.050 no
    C18 C21 H213 . . . 110.056 no
    H211 C21 H213 . . . 108.699 no
    H212 C21 H213 . . . 110.158 no
    C18 C22 H221 . . . 114.558 no
    C18 C22 H222 . . . 113.225 no
    H221 C22 H222 . . . 107.285 no
    C18 C22 H223 . . . 107.279 no
    H221 C22 H223 . . . 106.580 no
    H222 C22 H223 . . . 107.508 no
