Sequential Ring-Closing Metathesis and Nitrone Cycloaddition on Glucose-Derived Substrates: A Divergent Approach to Analogues of Spiroannulated Carbanucleosides and Conformationally Locked Nucleosides
Sk. Sahabuddin; Ashim Roy; Michael G. B. Drew; Biswajit Gopal Roy; Basudeb Achari; Sukhendu B. Mandal; Journal of Organic Chemistry 71 (2006) 5980–5992; doi:10.1021/jo0606554

data_4021839
_publ_section_title
;
 Sequential Ring-Closing Metathesis and Nitrone Cycloaddition on
 Glucose-Derived Substrates: A Divergent Approach to Analogues of
 Spiroannulated Carbanucleosides and Conformationally Locked Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5980
_journal_page_last               5992
_journal_paper_doi               10.1021/jo0606554
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C14 H17 N O4'
_chemical_formula_weight         263.28
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.240(9)
_cell_length_b                   10.604(12)
_cell_length_c                   19.21(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1271(3)
_computing_cell_refinement       XDS
_computing_data_collection       'XDS (Kabsch, 1988)'
_computing_data_reduction        XDS
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.872
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device       'Marresearch Image Plate'
_diffrn_measurement_method
'95 frames at 2 degree intervals, counting time 2 min.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5729
_diffrn_reflns_theta_full        25.74
_diffrn_reflns_theta_max         25.74
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelopiped
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.1(15)
_refine_ls_extinction_coef       0.040(6)
_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   0.936
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0823P)^2^+0.1721P] where P=(Fo^2^+2Fc^2^)/3 

;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                1811
_reflns_number_total             2129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0606554si20060515_023810_4.cif
_cod_database_code               4021839