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_4030543
_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         'C10 H17 N O4'
_chemical_formula_sum            'C10 H17 N O4'
_chemical_formula_weight         215.24
_chemical_name_common            methyloxazinane
_chemical_name_systematic
;
((2R,4aS,6aR,7R,9aS)-2-methyloctahydrofuro[3',4':2,3]furo[3,4-d][1,3]oxazin-7-yl)methanol
;
_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   mixed
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6184(3)
_cell_length_b                   9.1016(4)
_cell_length_c                   15.0206(7)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.64
_cell_measurement_theta_min      2.71
_cell_volume                     1041.52(8)
_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 0.962
_diffrn_measured_fraction_theta_max 0.970
_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  0.0523
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17162
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.694
_diffrn_reflns_theta_min         2.998
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1298 before and 0.0685 after correction.
The Ratio of minimum to maximum transmission is 0.8847.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1124 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         3144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0852P)^2^+0.1380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1281
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2802
_reflns_number_total             3144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502672x_si_007.cif
_cod_data_source_block           sd2012_0m
_cod_database_code               4030543
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              11439
_shelx_hkl_checksum              83292