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_4030955
_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_sum            'C21 H22 N2 O4 Si'
_chemical_formula_weight         394.50
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.372(3)
_cell_angle_beta                 95.057(3)
_cell_angle_gamma                98.899(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6005(3)
_cell_length_b                   10.3300(3)
_cell_length_c                   15.2977(5)
_cell_measurement_reflns_used    10132
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      1.00000
_cell_measurement_theta_min      0.78186
_cell_volume                     1018.22(7)
_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_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23514
_diffrn_reflns_theta_full        78.84
_diffrn_reflns_theta_max         78.84
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    1.264
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0201P)^2^+0.9761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                3713
_reflns_number_total             4259
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            4ab.cif
_cod_data_source_block           pg-ea
_cod_depositor_comments
'Adding full bibliography for 4030954--4030956.cif.'
_cod_original_cell_volume        1018.21(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4030955