Exploitation of in Situ Generated Sugar-Based Olefin Keto-Nitrones: Synthesis of Carbocycles, Heterocycles, and Nucleoside Derivatives.
Das, Soumendra Nath; Chowdhury, Arpan; Tripathi, Neha; Jana, Prithwish K.; Mandal, Sukhendu B.; The Journal of organic chemistry 80 (2014) 1136–; doi:10.1021/jo502672x

data_4030538
_publ_section_title
;
 Exploitation of in Situ Generated Sugar-Based Olefin Keto-Nitrones:
 Synthesis of Carbocycles, Heterocycles, and Nucleoside Derivatives.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1136
_journal_paper_doi               10.1021/jo502672x
_journal_volume                  80
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C29 H31 N O5'
_chemical_formula_sum            'C29 H31 N O5'
_chemical_formula_weight         473.55
_chemical_name_common            isoxazolidine
_chemical_name_systematic
;
(3aS,5aS,7R,8R,8aS)-1-benzyl-8-(benzyloxy)-7-((benzyloxy)methyl)hexahydro-1H-furo
[2',3':2,3]furo[3,4-c]isoxazole 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.152(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8763(4)
_cell_length_b                   9.3567(7)
_cell_length_c                   22.8256(16)
_cell_measurement_reflns_used    5205
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.76
_cell_measurement_theta_min      2.35
_cell_volume                     1249.94(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.793
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.793
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16188
_diffrn_reflns_point_group_measured_fraction_full 0.787
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         23.129
_diffrn_reflns_theta_min         0.896
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1148 before and 0.0480 after correction.
The Ratio of minimum to maximum transmission is 0.9055.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1212 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(4)
_refine_ls_extinction_coef       0.019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         3548
_refine_ls_number_restraints     157
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0812P)^2^+0.0049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.781
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2931
_reflns_number_total             3548
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502672x_si_005.cif
_cod_data_source_block           sd_ac_1_090511_0m
_cod_database_code               4030538
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 C26, C27, C28, C29
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C23A, C24A, C29A, C28A, C27A, C26A, C25A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C23, C24, C29, C28, C27, C26, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C26 \\sim C27 \\sim C28 \\sim C29: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C24 \\sim C24A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C25 \\sim C25A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C26 \\sim C26A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C27 \\sim C27A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C28 \\sim C28A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C29 \\sim C29A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C23 \\sim C23A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C23A \\sim C24A \\sim C29A \\sim C28A \\sim C27A \\sim C26A \\sim C25A: within
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C23 \\sim C24 \\sim C29 \\sim C28 \\sim C27 \\sim C26 \\sim C25: within 1.7A
with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=
 Sof(H26A)=Sof(C27A)=Sof(H27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=1-FVAR(1)
 Sof(C24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=Sof(C28)=
 Sof(H28)=Sof(C29)=Sof(H29)=Sof(C23A)=Sof(H23C)=Sof(H23D)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C14(H14), N1(H1A)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C15(H15A,H15B), C16(H16A,H16B), C23(H23A,H23B),
 C23A(H23C,H23D)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C11(H11),
  C25A(H25A), C26A(H26A), C27A(H27A), C28A(H28A), C29A(H29A)
;
_shelx_res_checksum              94603
_shelx_hkl_checksum              77906