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_4030540
_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         'C18 H23 N O5'
_chemical_formula_sum            'C18 H23 N O5'
_chemical_formula_weight         333.37
_chemical_name_common            Pyranoisoxazole
_chemical_name_systematic
;
(3aR,5aR,7aR,10aS,10bR)-1-benzyl-9,9-dimethyloctahydro-[1,3]dioxolo
[4'',5'':4',5']pyrano[2',3':2,3]furo[3,4-c]isoxazole
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.1419(10)
_cell_length_b                   20.457(3)
_cell_length_c                   27.077(4)
_cell_measurement_reflns_used    4080
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.07
_cell_measurement_theta_min      2.47
_cell_volume                     3402.1(9)
_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 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1062
_diffrn_reflns_av_unetI/netI     0.1102
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            32205
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.567
_diffrn_reflns_theta_min         1.248
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1398 before and 0.0997 after correction.
The Ratio of minimum to maximum transmission is 0.6416.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         7719
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1584
_refine_ls_R_factor_gt           0.0721
_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^)+(0.1172P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.2356
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3732
_reflns_number_total             7719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502672x_si_006.cif
_cod_data_source_block           subh_29112010_0m_a
_cod_database_code               4030540
_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 C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O10A-N007 \\sim O10B-N007
 with sigma of 0.02
 O10A-C19 \\sim O10B-C19
 with sigma of 0.02
 C31-C30 \\sim C31-C30A
 with sigma of 0.02
 N007-C30 \\sim N007-C30A
 with sigma of 0.02
 C36-C31 \\sim C36-C35 \\sim C35-C34 \\sim C34-C33 \\sim C33-C32 \\sim C32-C31
 with sigma of 0.02
3. Rigid bond restraints
 C30, C30A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C30 \\sim C30A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
5. Rigid body (RIGU) restrains
 C31, C36, C35, C34, C33, C32
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(O10B)=Sof(H19C)=Sof(H19D)=1-FVAR(1)
 Sof(H19A)=Sof(H19B)=Sof(O10A)=FVAR(1)
 Sof(C30A)=Sof(H30C)=Sof(H30D)=1-FVAR(2)
 Sof(C30)=Sof(H30A)=Sof(H30B)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C8(H8), C20(H20), C23(H23), C25(H25), C26(H26)
7.b Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B), C1(H1A,H1B), C3(H3A,H3B), C6(H6A,H6B), C19(H19A,H19B),
 C19(H19C,H19D), C22(H22A,H22B), C24(H24A,H24B), C30A(H30C,H30D), C30(H30A,H30B)
7.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36)
7.d Fitted hexagon refined as free rotating group:
 C31(C32,C33,C34,C35,C36)
7.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C)
;
_shelx_res_checksum              13226
_shelx_hkl_checksum              98621