An Experimental and Theoretical Study of the Type C Enone Rearrangement: Mechanistic and Exploratory Organic Photochemistry1
Howard E. Zimmerman; Evgueni E. Nesterov; Journal of the American Chemical Society 125 (2003) 5422–5430; doi:10.1021/ja028631b

data_4113691
_publ_section_title
;
 An Experimental and Theoretical Study of the Type C Enone Rearrangement:
 Mechanistic and Exploratory Organic Photochemistry1
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5422
_journal_page_last               5430
_journal_paper_doi               10.1021/ja028631b
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C22 H24 O'
_chemical_formula_weight         304.41
_chemical_melting_point          445(1)
_chemical_name_systematic
;
1-tert-butyl-endo-2-(4-cyanophenyl)-5-phenylbicyclo[3.1.0]hexan-3-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                 100.168(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2034(9)
_cell_length_b                   6.8456(6)
_cell_length_c                   25.029(2)
_cell_measurement_temperature    173(2)
_cell_volume                     1720.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10208
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.2950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1667
_reflns_number_gt                2944
_reflns_number_total             4163
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja028631bsi20030220_045416.cif
_cod_data_source_block           zimm
_cod_database_code               4113691