Face-Selective Diels-Alder Reactions between Unsymmetrical Cyclohexadienes and Symmetric trans-Dienophile: An Experimental and Computational Investigation
Saswati Lahiri; Somnath Yadav; Srirupa Banerjee; Mahendra P. Patil; Raghavan B. Sunoj; Journal of Organic Chemistry 73 (2008) 435–444; doi:10.1021/jo701884d

data_4023196
_publ_section_title
;
 Face-Selective Diels-Alder Reactions between Unsymmetrical
 Cyclohexadienes and Symmetric trans-Dienophile: An Experimental
 and Computational Investigation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              435
_journal_page_last               444
_journal_paper_doi               10.1021/jo701884d
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C25 H24 O3'
_chemical_formula_weight         370.43
_chemical_melting_point          174
_chemical_name_systematic        8,9-Dibenzoylhexahydro-3a,6-ethano-inden-5-one
_space_group_IT_number           14
_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                90.00
_cell_angle_beta                 91.149(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.005(5)
_cell_length_b                   14.836(8)
_cell_length_c                   14.242(8)
_cell_measurement_reflns_used    875
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.21
_cell_measurement_theta_min      2.65
_cell_volume                     1902.2(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\f and \w 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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13797
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_correction_T_min  0.9235
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0717P)^2^+0.4280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1222
_reflns_number_gt                2925
_reflns_number_total             3467
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701884d-File003.cif
_cod_data_source_block           sy7d4_m_(3nx)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023196