Regioselective Transition-Metal-Free Synthesis of 2-(Trimethylsilylmethylene)pyrrol-3-ones by Thermal Cyclization of Acetylenic Enamines.
Golubev, Pavel R.; Pankova, Alena S.; Kuznetsov, Mikhail A.; The Journal of organic chemistry 80 (2015) 4545–4552; doi:10.1021/acs.joc.5b00398

data_4030956
_publ_section_title
;
 Regioselective Transition-Metal-Free Synthesis of
 2-(Trimethylsilylmethylene)pyrrol-3-ones by Thermal Cyclization of
 Acetylenic Enamines.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4545
_journal_page_last               4552
_journal_paper_doi               10.1021/acs.joc.5b00398
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C19 H20 N2 O4 Si'
_chemical_formula_sum            'C19 H20 N2 O4 Si'
_chemical_formula_weight         368.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-02-17
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.7185(10)
_cell_length_b                   16.4457(17)
_cell_length_c                   21.179(2)
_cell_measurement_reflns_used    5022
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.7794
_cell_measurement_theta_min      2.6984
_cell_volume                     3733.3(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_details
;
  1 omega  -78.00  -41.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661 -178.0000   90.0000 37

  2 omega  -15.00   45.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661   57.0000   60.0000 60

  3 omega  -18.00   47.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -19.0000 -150.0000 65

  4 omega  -99.00  -70.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661 -178.0000 -150.0000 29

  5 omega  -37.00  -10.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661  -38.0000   60.0000 27

  6 omega   53.00   86.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  173.0000  130.0000 33

  7 omega  -12.00   16.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -19.0000 -180.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0304593000
_diffrn_orient_matrix_UB_12      0.0242076000
_diffrn_orient_matrix_UB_13      0.0230080000
_diffrn_orient_matrix_UB_21      0.0315738000
_diffrn_orient_matrix_UB_22      -0.0348536000
_diffrn_orient_matrix_UB_23      0.0114390000
_diffrn_orient_matrix_UB_31      0.0497404000
_diffrn_orient_matrix_UB_32      0.0073740000
_diffrn_orient_matrix_UB_33      -0.0214354000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19349
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.70
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1552
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+2.2395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                3464
_reflns_number_total             4277
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            4ar.cif
_cod_data_source_block           pg_frf
_cod_depositor_comments
'Adding full bibliography for 4030954--4030956.cif.'
_cod_original_cell_volume        3733.2(6)
_cod_database_code               4030956
_chemical_oxdiff_formula         'Si C20 O4 N2 H15'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51