Asymmetric Diels–Alder reaction of 3-(acyloxy)acryloyl oxazolidinones: optically active synthesis of a high-affinity ligand for potent HIV-1 protease inhibitors
Ghosh, Arun K.; Grillo, Alessandro; Kovela, Satish; Brindisi, Margherita; RSC Advances 9 (2019) 41755–; doi:10.1039/C9RA10178K

data_7239644
_publ_section_title
;
 Asymmetric Diels--Alder reaction of 3-(acyloxy)acryloyl oxazolidinones:
 optically active synthesis of a high-affinity ligand for potent HIV-1
 protease inhibitors
;
_journal_issue                   71
_journal_name_full               'RSC Advances'
_journal_page_first              41755
_journal_paper_doi               10.1039/C9RA10178K
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_sum            'C16 H15 N O6'
_chemical_formula_weight         317.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-09-25 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.854(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8717(4)
_cell_length_b                   7.6590(4)
_cell_length_c                   14.4338(7)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      36.3053
_cell_measurement_theta_min      3.0255
_cell_volume                     743.46(7)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_collection       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_refinement
;  
SHELXL-2016/6 (Sheldrick, 2015, 2016), 
SHELXLE Rev714 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24622
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.138
_diffrn_reflns_theta_min         3.025
_diffrn_source                   'sealed tube X-ray source'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         5530
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0736P)^2^+0.0171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                4726
_reflns_number_total             5530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra10178k2.cif
_cod_data_source_block           AG_01_082_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7239644
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              21410