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_4030541
_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         'C25 H29 N O5'
_chemical_formula_sum            'C25 H29 N O5'
_chemical_formula_weight         423.49
_chemical_name_common            Cyclopentaisooxazole
_chemical_name_systematic
;
(3aR,5R,5aS,6aR,9aR,9bR)-1-benzyl-5-(benzyloxy)-8,8-dimethyloctahydro-
[1,3]dioxolo[4'',5'':4',5']furo[3',2':1,5]cyclopenta[1,2-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             2014-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.916(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.660(2)
_cell_length_b                   10.965(2)
_cell_length_c                   10.599(2)
_cell_measurement_reflns_used    6447
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1114.5(4)
_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 0.969
_diffrn_measured_fraction_theta_max 0.998
_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  0.0233
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12860
_diffrn_reflns_point_group_measured_fraction_full 0.865
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.124
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1584 before and 0.0713 after correction.
The Ratio of minimum to maximum transmission is 0.9017.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1082 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3497
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0804P)^2^+0.0871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1208
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    0.747
_reflns_Friedel_fraction_max     0.770
_reflns_number_gt                2934
_reflns_number_total             3497
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502672x_si_004.cif
_cod_data_source_block           sd_c6_n
_cod_database_code               4030541
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H22 of C22, H16 of C16, H18 of C18, H15 of C15, H21 of
  C21, H17 of C17, H19A of C19, H14 of C14, H24 of C24, H23 of C23, H25 of C25,
  H3 of C3, H4 of C4, H7 of C7, H8 of C8
 At 1.5 times of:
  All C(H,H,H) groups
 At 1 times of:
  H19B of C19
2. Restrained distances
 C20-C19 \\sim C20-C19B
 with sigma of 0.02
 C25-C20 \\sim C25-C24 \\sim C24-C23 \\sim C23-C22 \\sim C22-C21 \\sim C21-C20
 with sigma of 0.02
 O1-C1 \\sim O1B-C1
 with sigma of 0.02
 O1B-C19B \\sim O1-C19
 with sigma of 0.02
3. Rigid bond restraints
 C19, C19B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C19: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C19: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C19 \\sim C19B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
5. Rigid body (RIGU) restrains
 O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H1B)=Sof(C19B)=Sof(H19C)=Sof(H19D)=Sof(O1B)=1-FVAR(1)
 Sof(H1A)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(O1)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C1(H1A), C1(H1B), C3(H3), C4(H4), C7(H7), C8(H8)
7.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C12(H12A,H12B), C19(H19A,H19B), C19B(H19C,H19D)
7.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25)
7.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              92784
_shelx_hkl_checksum              17035