Stereoselective Desymmetrization of Cyclohexadienone-Tethered Enones: Efficient Access to Highly Strained Polycyclic Indoles
Thopate, Satish B.; Jadhav, Sandip B.; Nanubolu, Jagadeesh Babu; Chegondi, Rambabu; ACS Catalysis  (2019) 10012–; doi:10.1021/acscatal.9b03560

data_4514893
_publ_section_title
;
 Stereoselective Desymmetrization of Cyclohexadienone-Tethered Enones:
 Efficient Access to Highly Strained Polycyclic Indoles
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10012
_journal_paper_doi               10.1021/acscatal.9b03560
_journal_year                    2019
_chemical_formula_moiety         'C28 H29 N O3'
_chemical_formula_sum            'C28 H29 N O3'
_chemical_formula_weight         427.52
_chemical_name_systematic
'14-(4-ethylbenzoyl)-4a,8-dimethyl-3,4,4a,6,7,13a-hexahydro-4,7-methanobenzo[2,3][1,4]oxazepino[4,5- a]indol-2(1 H)-one'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6581(13)
_cell_length_b                   8.4966(4)
_cell_length_c                   27.1209(15)
_cell_measurement_reflns_used    4519
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.736
_cell_measurement_theta_min      2.558
_cell_volume                     4529.9(4)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1632
_diffrn_reflns_av_unetI/netI     0.0923
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            38580
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.559
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0052(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1703
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1493
_refine_ls_wR_factor_ref         0.1989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1895
_reflns_number_total             3980
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03560_si_003.cif
_cod_data_source_block           KA768_0m
_cod_database_code               4514893
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              18779
_shelx_hkl_checksum              93084