Development of a Large-Scale Route to Glecaprevir: Synthesis of the Side Chain and Final Assembly
Hill, David R.; Abrahamson, Michael J.; Lukin, Kirill A.; Towne, Timothy B.; Engstrom, Kenneth M.; Reddy, Rajarathnam E.; Kielbus, Angelica B.; Pelc, Matthew J.; Mei, Jianzhang; Nere, Nandkishor K.; Chen, Shuang; Henry, Rodger; Chemburkar, Sanjay; Ding, Chen; Zhang, Hongqiang; Cink, Russell D.; Organic Process Research & Development  (2020) –; doi:10.1021/acs.oprd.0c00245

data_1558672
_publ_section_title
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 Development of a Large-Scale Route to Glecaprevir: Synthesis of the Side
 Chain and Final Assembly
;
_journal_name_full               'Organic Process Research &amp; Development'
_journal_paper_doi               10.1021/acs.oprd.0c00245
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H33 F2 N O4'
_chemical_formula_weight         389.47
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                106.366(3)
_cell_angle_beta                 94.675(3)
_cell_angle_gamma                90.873(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6295(5)
_cell_length_b                   10.2499(5)
_cell_length_c                   12.1993(7)
_cell_measurement_reflns_used    8399
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.873
_cell_measurement_theta_min      3.4915
_cell_volume                     1031.06(10)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.871
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'phi-omega scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.871
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11367
_diffrn_reflns_point_group_measured_fraction_full 0.767
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.925
_diffrn_reflns_theta_min         3.791
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     503
_refine_ls_number_reflns         5728
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+0.2954P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0866
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.663
_reflns_Friedel_fraction_max     0.708
_reflns_number_gt                5038
_reflns_number_total             5728
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            op0c00245_si_003.cif
_cod_data_source_block           Compound19b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
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_cod_database_code               1558672
_shelxl_version_number           2013-2
_shelx_res_checksum              28356
_shelx_hkl_checksum              67673