SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives.
Sekine, Kohei; Sadamitsu, Yuta; Yamada, Tohru; Organic letters 17 (2015) 5706–5709; doi:10.1021/acs.orglett.5b03023

data_1540602
_publ_section_title
;
 SilverCatalyzed Cascade Carboxylation and Cyclization of
 Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5706
_journal_page_last               5709
_journal_paper_doi               10.1021/acs.orglett.5b03023
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C13 H12 O2'
_chemical_formula_sum            'C13 H12 O2'
_chemical_formula_weight         200.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                102.823(4)
_cell_angle_beta                 100.864(4)
_cell_angle_gamma                113.210(4)
_cell_formula_units_Z            2
_cell_length_a                   8.1069(11)
_cell_length_b                   8.3799(11)
_cell_length_c                   8.9188(11)
_cell_measurement_reflns_used    2987
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      25.0729
_cell_measurement_theta_min      2.4616
_cell_volume                     516.59(12)
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           (MoK\a)
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4588
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             214
_exptl_crystal_size_max          0.588
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0724P)^2^+0.1359P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1439
_reflns_number_gt                1463
_reflns_number_total             1741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03023_si_002.cif
_cod_data_source_block           I
_cod_database_code               1540602