Mitsunobu Coupling of Nucleobases and Alcohols: An Efficient, Practical Synthesis for Novel Nonsugar Carbon Nucleosides
Weibing Lu; Sujata Sengupta; Jeffrey L. Petersen; Novruz G. Akhmedov; Xiaodong Shi; Journal of Organic Chemistry 72 (2007) 5012–5015; doi:10.1021/jo070515+

data_4023960
_publ_section_title
;
 Mitsunobu Coupling of Nucleobases and Alcohols: An Efficient,
 Practical Synthesis for Novel Nonsugar Carbon Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5012
_journal_page_last               5015
_journal_paper_doi               10.1021/jo070515+
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C8 H4 Cl2 N4'
_chemical_formula_weight         227.05
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 98.9750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9928(3)
_cell_length_b                   20.7240(14)
_cell_length_c                   11.2562(8)
_cell_measurement_reflns_used    5200
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.68
_cell_volume                     920.01(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5645
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+0.2328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                1830
_reflns_number_total             2030
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070515+si20070312_112705.cif
_cod_data_source_block           ms14ccd
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023960