Asymmetric vinylogous Michael addition of 5-substituted-furan-2(3<i>H</i>)-ones to an α,β-unsaturated-γ-lactam.
Romaniszyn, Marta; Sieroń, Lesław; Albrecht, Łukasz; Organic & biomolecular chemistry 18 (2020) 8633–8637; doi:10.1039/d0ob01750g

data_7157734
_publ_section_title
;
 Asymmetric vinylogous Michael addition of
 5-substituted-furan-2(3<i>H</i>)-ones to an \a,\b-unsaturated-\g-lactam.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8633
_journal_page_last               8637
_journal_paper_doi               10.1039/d0ob01750g
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H20 Cl N O5'
_chemical_formula_sum            'C19 H20 Cl N O5'
_chemical_formula_weight         377.81
_chemical_melting_point          444
_chemical_name_systematic
;
(R)-tert-butyl 4-((R)-2-(4-chlorophenyl)-5-oxo-2,5-dihydrofuran-2-yl)-2-oxopyrrolidine-1-carboxylate
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-07-01 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.0027(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.62610(9)
_cell_length_b                   6.61723(11)
_cell_length_c                   14.2237(2)
_cell_measurement_reflns_used    21137
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.797
_cell_measurement_theta_min      4.636
_cell_volume                     897.20(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21820
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         4.64
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.152
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.309
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.74a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       Prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1295 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(6)
_refine_ls_extinction_coef       0.0042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'shelxl-2018/3 (sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0225
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0316P)^2^+0.2692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0589
_reflns_number_gt                3038
_reflns_number_total             3040
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d0ob01750g3.cif
_cod_data_source_block           dm_l
_cod_depositor_comments          'Adding full bibliography for 7157734.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7157734
_shelx_res_checksum              46090