The protecting-group free selective 3′-functionalization of nucleosides
McCabe Dunn, Jamie M.; Reibarkh, Mikhail; Sherer, Edward C.; Orr, Robert K.; Ruck, Rebecca T.; Simmons, Bryon; Bellomo, Ana; Chem. Sci. 8 (2017) 2804–; doi:10.1039/C6SC05081F

data_1545091
_publ_section_title
;
 The protecting-group free selective 3&#x2032;-functionalization of
 nucleosides
;
_journal_issue                   4
_journal_name_full               'Chem. Sci.'
_journal_page_first              2804
_journal_paper_doi               10.1039/C6SC05081F
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H17 F5 N O5 P'
_chemical_formula_sum            'C18 H17 F5 N O5 P'
_chemical_formula_weight         453.29
_chemical_name_systematic
;
isopropyl ((R)-(perfluorophenoxy)(phenoxy)phosphoryl)-D-alaninate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-01-05 deposited with the CCDC.
2017-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                74.879(2)
_cell_angle_beta                 84.088(2)
_cell_angle_gamma                80.148(2)
_cell_formula_units_Z            2
_cell_length_a                   5.2533(2)
_cell_length_b                   12.0015(5)
_cell_length_c                   16.3874(7)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      2.80
_cell_volume                     980.85(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23764
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        68.250
_diffrn_reflns_theta_max         68.457
_diffrn_reflns_theta_min         2.798
_diffrn_source                   'sealed-tube microsource X-ray generator'
_exptl_absorpt_coefficient_mu    1.976
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
(SADABS; Sheldrick, 2003) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       rod
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: isopropanol and water'
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
 Flack x determined using 2970 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.010(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         6829
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0466P)^2^+0.6819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_full    0.903
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                6574
_reflns_number_total             6829
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc05081f2.cif
_cod_data_source_block           mdl087
_cod_depositor_comments
;Adding full bibliography for 1545090--1545091.cif.

The following automatic conversions were performed:

'_atom_sites_solution_secondary' value 'diffmap' was changed to
'difmap'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_database_code               1545091
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.797
_shelx_estimated_absorpt_t_max   0.962
_shelx_res_checksum              50510
_shelx_hkl_checksum              54379