Synthesis of ABBV-168, a 2'-Bromouridine for the Treatment of Hepatitis C.
Voight, Eric A.; Brown, Brian S.; Greszler, Stephen N.; Halvorsen, Geoff T.; Zhao, Gang; Kruger, Albert W.; Hartung, John; Lukin, Kirill A.; Martinez, Steven R.; Moschetta, Eric G.; Tudesco, Michael T.; Ide, Nathan D.; The Journal of organic chemistry 84 (2019) 4723–4734; doi:10.1021/acs.joc.8b02341

data_4035936
_publ_section_title
;
 Synthesis of ABBV-168, a 2'-Bromouridine for the Treatment of Hepatitis
 C.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4723
_journal_page_last               4734
_journal_paper_doi               10.1021/acs.joc.8b02341
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H20 Br F O5'
_chemical_formula_weight         355.20
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.810(3)
_cell_length_b                   10.115(6)
_cell_length_c                   25.579(14)
_cell_measurement_reflns_used    1122
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.589
_cell_measurement_theta_min      3.1245
_cell_volume                     1503.2(14)
_computing_cell_refinement       'Apex2 v2.4-3 (Bruker, 2012)'
_computing_data_collection       'Apex2 v2.4-3 (Bruker, 2012)'
_computing_data_reduction        'Apex2 v2.4-3 (Bruker, 2012)'
_computing_molecular_graphics    'ORTEP-3 for Windows v2.01'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1646
_diffrn_reflns_av_unetI/netI     0.1988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            17960
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_min         1.592
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.761
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03 (Bruker AXS Inc., 2003'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    none
_exptl_crystal_description       rod
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details
;
 Flack x determined using 532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.783
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.783
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0103P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0694
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1899
_reflns_number_total             3442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02341_si_002.cif
_cod_data_source_block           compound21
_cod_original_cell_volume        1503.3(14)
_cod_database_code               4035936
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.608
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              94001
_shelx_hkl_checksum              70985