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_1545090
_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         'C22 H29 F N3 O9 P'
_chemical_formula_sum            'C22 H29 F N3 O9 P'
_chemical_formula_weight         529.45
_chemical_name_systematic
'isopropyl ((R)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-yl)oxy)(phenoxy)phosphoryl)-D-alaninate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.355(3)
_cell_length_b                   13.612(3)
_cell_length_c                   16.835(4)
_cell_measurement_reflns_used    2355
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.97
_cell_measurement_theta_min      4.18
_cell_volume                     2602.1(11)
_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 0.981
_diffrn_measured_fraction_theta_max 0.980
_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  0.0482
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11896
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        68.250
_diffrn_reflns_theta_max         68.339
_diffrn_reflns_theta_min         4.177
_diffrn_source                   'sealed-tube microsource X-ray generator'
_exptl_absorpt_coefficient_mu    1.480
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
(SADABS; Sheldrick, 2003) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and methanol'
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
; 
 Flack x determined using 1389 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0575P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                3860
_reflns_number_total             4596
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc05081f2.cif
_cod_data_source_block           mdl086
_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_original_cell_volume        2602.1(10)
_cod_database_code               1545090
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.842
_shelx_estimated_absorpt_t_max   0.971
_shelx_res_checksum              33995
_shelx_hkl_checksum              44972