Lewis Acid-Catalyzed Selective [2 + 2]-Cycloaddition and Dearomatizing Cascade Reaction of Aryl Alkynes with Acrylates.
Shen, Liang; Zhao, Kai; Doitomi, Kazuki; Ganguly, Rakesh; Li, Yong-Xin; Shen, Zhi-Liang; Hirao, Hajime; Loh, Teck-Peng; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b07997

data_4126416
_publ_section_title
;
 Lewis Acid-Catalyzed Selective [2 + 2]-Cycloaddition and Dearomatizing
 Cascade Reaction of Aryl Alkynes with Acrylates.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b07997
_journal_year                    2017
_chemical_formula_sum            'C16 H18 Br Cl O4'
_chemical_formula_weight         389.66
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 106.558(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0743(6)
_cell_length_b                   17.4986(10)
_cell_length_c                   10.3332(7)
_cell_measurement_reflns_used    2822
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      25.7861
_cell_measurement_theta_min      3.1066
_cell_volume                     1572.74(18)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22690
_diffrn_reflns_theta_full        31.17
_diffrn_reflns_theta_max         31.17
_diffrn_reflns_theta_min         2.62
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.798
_exptl_absorpt_correction_T_max  0.58
_exptl_absorpt_correction_T_min  0.34
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.975
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         5047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0280P)^2^+0.6202P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                3494
_reflns_number_total             5047
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07997_si_006.cif
_cod_data_source_block           I
_cod_database_code               4126416
_shelx_res_checksum              31330
_shelx_hkl_checksum              1255