Asymmetric Synthesis of an N-Acylpyrrolidine for Inhibition of HCV Polymerase
Armel A. Agbodjan; Bob E. Cooley; Royston C. B. Copley; John A. Corfield; Roy C. Flanagan; Bobby N. Glover; Rossella Guidetti; David Haigh; Peter D. Howes; Mary M. Jackson; Richard T. Matsuoka; Katrina J. Medhurst; Alan Millar; Matthew J. Sharp; Martin J. Slater; Jennifer F. Toczko; Shiping Xie; Journal of Organic Chemistry 73 (2008) 3094–3102; doi:10.1021/jo800062c

data_4023369
_publ_contact_author
;
Shiping Xie,
Chemical Development, 
GlaxoSmithKline, 
Research Triangle Park, 
North Carolina 27709, 
USA
;
_publ_contact_author_email       Shiping.X.Xie@GSK.com
_publ_contact_author_fax         '+1 919 483 3706'
_publ_contact_author_phone       '+1 919 483 6642'
_publ_section_title
;
 Asymmetric Synthesis of an N-Acylpyrrolidine for Inhibition
 of HCV Polymerase
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3094
_journal_page_last               3102
_journal_paper_doi               10.1021/jo800062c
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H42 N2 O5 S, 0.136 C2 H3 N'
_chemical_formula_sum            'C29.27 H42.41 N2.14 O5 S'
_chemical_formula_weight         536.29
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.5527(12)
_cell_length_b                   14.5527(12)
_cell_length_c                   29.858(3)
_cell_measurement_reflns_used    200
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      19.87
_cell_measurement_theta_min      4.30
_cell_volume                     6323.4(10)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs, 1990-2000)'
_computing_molecular_graphics    'SHELXTL V6.10 [NT] (Bruker, 2001)'
_computing_publication_material  'SHELXTL V6.10 [NT] (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL V6.10 [NT] (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.10 [NT] (Bruker, 2001)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.6 mm double-pinhole'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'normal focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5517
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         4.55
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.768
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             2312
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0210P)^2^+2.2537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                4597
_reflns_number_total             5517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800062c-File001.cif
_cod_data_source_block           10
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023369
_computing_data_merging          'SHELXTL V6.10 [NT] (Bruker, 2001)'