Synthesis of Oxazolidin-4-ones: Domino O-Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation.
El Bouakher, Abderrahman; Le Goff, Ronan; Tasserie, Jordan; Lhoste, Jérôme; Martel, Arnaud; Comesse, Sébastien; Organic letters 18 (2016) 2383–2386; doi:10.1021/acs.orglett.6b00851

data_1543217
_publ_section_title
;
 Synthesis of Oxazolidin-4-ones: Domino
 O-Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2383
_journal_page_last               2386
_journal_paper_doi               10.1021/acs.orglett.6b00851
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_sum            'C20 H21 N O5 S'
_chemical_formula_weight         387.44
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.420(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7950(5)
_cell_length_b                   21.5130(13)
_cell_length_c                   11.4883(7)
_cell_measurement_reflns_used    323
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      3.3
_cell_volume                     1917.9(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            42466
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SHELX76; Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.137
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0833
_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^)+(0.1356P)^2^+2.8401P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2412
_refine_ls_wR_factor_ref         0.2805
_reflns_number_gt                2420
_reflns_number_total             3516
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00851_si_004.cif
_cod_data_source_block           C20H21NO5S
_cod_depositor_comments
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The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1543214--1543218.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1543217