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_1558670
_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                106.432(4)
_cell_angle_beta                 94.759(4)
_cell_angle_gamma                90.868(4)
_cell_formula_units_Z            2
_cell_length_a                   8.6196(7)
_cell_length_b                   10.2451(7)
_cell_length_c                   12.2006(8)
_cell_measurement_reflns_used    3465
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      60.6915
_cell_measurement_theta_min      3.793
_cell_volume                     1029.01(13)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.812
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega-phi scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.812
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11343
_diffrn_reflns_point_group_measured_fraction_full 0.713
_diffrn_reflns_point_group_measured_fraction_max 0.794
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         63.112
_diffrn_reflns_theta_min         3.793
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_description       fragment
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1441 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.20(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         5311
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.1211P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.614
_reflns_Friedel_fraction_max     0.684
_reflns_number_gt                3809
_reflns_number_total             5311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            op0c00245_si_002.cif
_cod_data_source_block           Compound19a
_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               1558670
_shelxl_version_number           2013-2
_shelx_res_checksum              22635
_shelx_hkl_checksum              75026