Regioselective Synthesis of Bicyclic and Polycyclic Systems by Cycloaddition Reactions of Alkenyl p-Benzoquinones
Bisht, Shweta; Rani, Rashmi; Peddinti, Rama Krishna; The Journal of Organic Chemistry  (2017) –; doi:10.1021/acs.joc.7b02377

data_4033263
_publ_section_title
;
 Regioselective Synthesis of Bicyclic and Polycyclic Systems by
 Cycloaddition Reactions of Alkenyl p-Benzoquinones
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02377
_journal_year                    2017
_chemical_formula_moiety         'C20 H26 O8'
_chemical_formula_sum            'C20 H26 O8'
_chemical_formula_weight         394.41
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                90.000(5)
_cell_angle_beta                 103.551(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   10.377(5)
_cell_length_b                   22.737(5)
_cell_length_c                   8.394(5)
_cell_measurement_reflns_used    4553
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.366
_cell_measurement_theta_min      0.979
_cell_volume                     1925.4(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector''
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0875
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            24989
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.79
_diffrn_standards_number         29739
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.263
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3580
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.263
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0588
_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          0.1660
_refine_ls_wR_factor_ref         0.2172
_reflns_number_gt                2136
_reflns_number_total             3580
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02377_si_002.cif
_cod_data_source_block           ups3140rkp_ssb13_0ma
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4033263