Cycloaddition Reaction of Vinylphenylfurans and Dimethyl Acetylenedicarboxylate to [8 + 2] Isomers via Tandem [4 + 2]/Diradical Alkene-Alkene Coupling/[1,3]-H Shift Reactions: Experimental Exploration and DFT Understanding of Reaction Mechanisms.
Chen, Kai; Wu, Feng; Ye, Lijuan; Tian, Zi-You; Yu, Zhi-Xiang; Zhu, Shifa; The Journal of organic chemistry 81 (2016) 8155–8168; doi:10.1021/acs.joc.6b00792

data_4036887
_publ_section_title
;
 Cycloaddition Reaction of Vinylphenylfurans and Dimethyl
 Acetylenedicarboxylate to [8 + 2] Isomers via Tandem [4 + 2]/Diradical
 Alkene-Alkene Coupling/[1,3]-H Shift Reactions: Experimental Exploration
 and DFT Understanding of Reaction Mechanisms.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8155
_journal_page_last               8168
_journal_paper_doi               10.1021/acs.joc.6b00792
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C18 H16 O5'
_chemical_formula_weight         312.31
_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_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.004(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1905(3)
_cell_length_b                   22.6990(8)
_cell_length_c                   8.3591(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1478.00(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4035
_diffrn_reflns_theta_full        62.32
_diffrn_reflns_theta_max         62.32
_diffrn_reflns_theta_min         3.89
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  0.9196
_exptl_absorpt_correction_T_min  0.8481
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1411
_reflns_number_gt                2041
_reflns_number_total             2275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00792_si_002.cif
_cod_data_source_block           zsfhjld
_cod_original_cell_volume        1478.00(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036887