AlCl₃-Catalyzed Ring Expansion Cascades of Bicyclic Cyclobutenamides Involving Highly Strained Cis,Trans-Cycloheptadienone Intermediates.
Wang, Xiao-Na; Krenske, Elizabeth H.; Johnston, Ryne C.; Houk, K. N.; Hsung, Richard P.; Journal of the American Chemical Society 137 (2015) 5596–5601; doi:10.1021/jacs.5b02561

data_4129415
_publ_section_title
;
 AlCl&#x2083;-Catalyzed Ring Expansion Cascades of Bicyclic
 Cyclobutenamides Involving Highly Strained Cis,Trans-Cycloheptadienone
 Intermediates.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5596
_journal_page_last               5601
_journal_paper_doi               10.1021/jacs.5b02561
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 N2 O5 S'
_chemical_formula_sum            'C22 H22 N2 O5 S'
_chemical_formula_weight         426.48
_chemical_name_common            13118b
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 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                 99.519(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.8494(6)
_cell_length_b                   9.7009(4)
_cell_length_c                   14.1516(6)
_cell_measurement_reflns_used    2753
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      4.72
_cell_volume                     2010.50(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 PHOTON-100'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'normal parabolic mirrors'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17037
_diffrn_reflns_theta_full        68.35
_diffrn_reflns_theta_max         68.35
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    1.756
_exptl_absorpt_correction_T_max  0.8723
_exptl_absorpt_correction_T_min  0.6679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008/1)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.131(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         7214
_refine_ls_number_restraints     243
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0415P)^2^+1.0328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                6911
_reflns_number_total             7214
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b02561_si_005.cif
_cod_data_source_block           13118b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4129415