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_4129416
_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_formula_moiety         'C23 H28 N2 O5 S'
_chemical_formula_sum            'C23 H28 N2 O5 S'
_chemical_formula_weight         444.53
_chemical_name_common            13310b
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 99.408(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2847(13)
_cell_length_b                   10.7604(8)
_cell_length_c                   11.6974(9)
_cell_measurement_reflns_used    2982
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      68.00
_cell_measurement_theta_min      2.59
_cell_volume                     2146.3(3)
_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-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXT (Sheldrick 2013)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker-AXS PHOTON-100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'normal, parabolic mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14179
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.222
_diffrn_reflns_theta_min         2.591
_diffrn_source                   'ImuS micro-focus'
_exptl_absorpt_coefficient_mu    1.663
_exptl_absorpt_correction_T_max  0.9289
_exptl_absorpt_correction_T_min  0.7885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+1.5624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3461
_reflns_number_total             3874
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b02561_si_004.cif
_cod_data_source_block           13310b
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4129416
_shelx_estimated_absorpt_t_min   0.789
_shelx_estimated_absorpt_t_max   0.929
_shelxl_version_number           2013-3
_shelx_res_checksum              96673
_shelx_hkl_checksum              52955