Synthesis of Highly Substituted 3-Pyrrolin-2-ones from N,N-Disubstituted α-Amino Acids.
Samper Barceló, Víctor; Bienz, Stefan; The Journal of organic chemistry 83 (2018) 2734–2743; doi:10.1021/acs.joc.7b03187

data_4034969
_publ_section_title
;
 Synthesis of Highly Substituted 3-Pyrrolin-2-ones from N,N-Disubstituted
 \a-Amino Acids.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2734
_journal_page_last               2743
_journal_paper_doi               10.1021/acs.joc.7b03187
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C10 H10 Cl N O2 S'
_chemical_formula_sum            'C10 H10 Cl N O2 S'
_chemical_formula_weight         243.70
_chemical_melting_point          404.9
_chemical_name_systematic
3-chloro-5-methoxy-1-methyl-4-(2-thienyl)-1,5-dihydro-2H-pyrrol-2-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 109.471(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2094(2)
_cell_length_b                   14.5436(2)
_cell_length_c                   7.83158(19)
_cell_measurement_reflns_used    6583
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.2560
_cell_measurement_theta_min      2.7870
_cell_volume                     1096.34(4)
_computing_cell_refinement
'CrysAlisPro, Version 1.171.37.35g (Agilent Technologies, 2014)'
_computing_data_collection
'CrysAlisPro, Version 1.171.37.35g (Agilent Technologies, 2014)'
_computing_data_reduction
'CrysAlisPro, Version 1.171.37.35g (Agilent Technologies, 2014)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2014 and PLATON (Spek, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2008)'
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 'Atlas CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.444
_diffrn_reflns_theta_min         2.537
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.37.35g (Agilent Technologies, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0363P)^2^+0.7504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2180
_reflns_number_total             2460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03187_si_002.cif
_cod_data_source_block           8l
_cod_original_cell_volume        1096.35(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034969
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              26963
_shelx_hkl_checksum              38542