Synthesis of Conformationally Locked l-Deoxythreosyl Phosphonate Nucleosides Built on a Bicyclo[3.1.0]hexane Template
Hisao Saneyoshi; Jeffrey R. Deschamps; Victor E. Marquez; Journal of Organic Chemistry 75 (2010) 7659–7669; doi:10.1021/jo101475p

data_4025804
_publ_section_title
;
 Synthesis of Conformationally Locked l-Deoxythreosyl Phosphonate
 Nucleosides Built on a Bicyclo[3.1.0]hexane Template
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7659
_journal_page_last               7669
_journal_paper_doi               10.1021/jo101475p
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C11 H13 N5 O, H2 O'
_chemical_formula_sum            'C11 H15 N5 O2'
_chemical_formula_weight         249.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 108.523(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.496(6)
_cell_length_b                   8.2267(18)
_cell_length_c                   10.584(2)
_cell_measurement_reflns_used    3431
_cell_measurement_temperature    144(2)
_cell_measurement_theta_max      28.53
_cell_measurement_theta_min      2.56
_cell_volume                     2435.2(9)
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001b)'
_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001b)'
_computing_data_reduction
;
Bruker SAINT v6.45 (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001a)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000a)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000a)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000a)'
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000a)'
_diffrn_ambient_temperature      144(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX 2 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14786
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.60
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10, Bruker (2000b)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flat_rod
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.473
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.079
_refine_diff_density_max         1.493
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_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   1.166
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         6644
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0757
_refine_ls_shift/su_max          0.195
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1361P)^2^+0.5194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2388
_reflns_number_gt                4970
_reflns_number_total             6644
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo101475p_si_003.cif
_cod_data_source_block           compound_(-)-26
_cod_original_cell_volume        2435.1(9)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4025804