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_4030544
_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         'C21 H27 N O6'
_chemical_formula_sum            'C21 H27 N O6'
_chemical_formula_weight         389.43
_chemical_name_common            'oxazocinyl acetate'
_chemical_name_systematic
;
(3S,5R,6aR,7aR,10aR,10bR)-1-benzyl-9,9-dimethyloctahydro-3,10b-methano
[1,3]dioxolo[4',5':4,5]furo[3,2-c][1,2]oxazocin-5-yl acetate
;
_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                 108.29(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.804(4)
_cell_length_b                   5.996(2)
_cell_length_c                   13.750(5)
_cell_measurement_reflns_used    4034
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.25
_cell_measurement_theta_min      2.62
_cell_volume                     1002.3(6)
_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 0.935
_diffrn_measured_fraction_theta_max 0.947
_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  0.0460
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11748
_diffrn_reflns_point_group_measured_fraction_full 0.836
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.770
_diffrn_reflns_theta_min         1.675
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1286 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.8859.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 731 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.2(10)
_refine_ls_extinction_coef       0.027(7)
_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   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3963
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0890P)^2^+0.1706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1965
_reflns_Friedel_coverage         0.617
_reflns_Friedel_fraction_full    0.713
_reflns_Friedel_fraction_max     0.707
_reflns_number_gt                2558
_reflns_number_total             3963
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502672x_si_003.cif
_cod_data_source_block           sd_nh_f_0m
_cod_original_cell_volume        1002.4(6)
_cod_database_code               4030544
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              92429
_shelx_hkl_checksum              84533