A rapid and divergent access to chiral azacyclic nucleoside analogues via highly enantioselective 1,3-dipolar cycloaddition of beta-nucleobase substituted acrylates
Qi-Liang Yang; Ming-Sheng Xie; Chao Xia; Huan-Li Sun; Dan-Jie Zhang; Ke-Xin Huang; Zhen Guo; Gui-Rong Qu; Hai-Ming Guo; Chem.Commun. 50 (2014) 14809–; doi:10.1039/C4cc06632D

data_7115985
_publ_section_title
;
 A rapid and divergent access to chiral azacyclic nucleoside analogues via
 highly enantioselective 1,3-dipolar cycloaddition of beta-nucleobase
 substituted acrylates
;
_journal_name_full               Chem.Commun.
_journal_page_first              14809
_journal_paper_doi               10.1039/C4cc06632D
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H25 Br Cl N5 O6 S'
_chemical_formula_weight         662.94
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 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            8
_cell_length_a                   21.051(4)
_cell_length_b                   28.357(6)
_cell_length_c                   13.136(3)
_cell_measurement_reflns_used    2602
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.548
_cell_measurement_theta_min      4.841
_cell_volume                     7841(3)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0984
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24307
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.207
_exptl_absorpt_correction_T_max  0.9096
_exptl_absorpt_correction_T_min  0.6705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2704
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_platon_squeeze_details          ' ?'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.019(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         6895
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0118P)^2^+0.1907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                3659
_reflns_number_total             6895
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc06632d2.cif
_cod_data_source_block           t
_cod_original_sg_symbol_H-M      C222(1)
_cod_database_code               7115985