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_4035937
_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            'C9 H10 Br F N2 O5'
_chemical_formula_weight         325.10
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   17.6590(15)
_cell_length_b                   17.6590(15)
_cell_length_c                   14.3682(12)
_cell_measurement_reflns_used    9238
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.3065
_cell_volume                     4480.6(7)
_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 0.999
_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  0.0704
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            53700
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         1.631
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.701
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5911
_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    1.928
_exptl_crystal_density_method    none
_exptl_crystal_description       parallelapiped
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 2009 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5154
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0179
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0265P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0439
_refine_ls_wR_factor_ref         0.0443
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4865
_reflns_number_total             5154
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02341_si_001.cif
_cod_data_source_block           compound14
_cod_depositor_comments
;

2021-04-11
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        4480.6(8)
_cod_original_formula_sum        'C10.29 H11.43 Br1.14 F1.14 N2.29 O5.71'
_cod_original_formula_units_Z    14
_cod_original_formula_weight     371.54
_cod_database_code               4035937
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.319
_shelx_estimated_absorpt_t_max   0.319
_shelx_res_checksum              36201
_shelx_hkl_checksum              8093