Rh-Catalyzed diastereoselective desymmetrization of enone tethered-cyclohexadienones via tandem arylative cyclization.
Jadhav, Sandip B.; Thopate, Satish B.; Nanubolu, Jagadeesh Babu; Chegondi, Rambabu; Organic & biomolecular chemistry 17 (2019) 1937–1946; doi:10.1039/c8ob02284d

data_7156490
_publ_section_title
;
 Rh-Catalyzed diastereoselective desymmetrization of enone
 tethered-cyclohexadienones via tandem arylative cyclization.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1937
_journal_page_last               1946
_journal_paper_doi               10.1039/c8ob02284d
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C29 H24 O3 S'
_chemical_formula_sum            'C29 H24 O3 S'
_chemical_formula_weight         452.54
_chemical_name_systematic
'4-benzoyl-3-(dibenzo[b,d]thophen-4-yl)-8a-methyl-3,4,4a,5-tetrahydro-2H chromen-6(8a H)-one'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-09-08 deposited with the CCDC.
2018-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.942(4)
_cell_length_b                   16.844(10)
_cell_length_c                   17.488(11)
_cell_measurement_reflns_used    8030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.843
_cell_measurement_theta_min      2.327
_cell_volume                     2339(2)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0665
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25848
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.329
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane and Hexane'
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1168 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5384
_refine_ls_number_restraints     204
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0529
_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          0.1230
_refine_ls_wR_factor_ref         0.1498
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3563
_reflns_number_total             5384
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02284d2.cif
_cod_data_source_block           KA437_0m
_cod_depositor_comments          'Adding full bibliography for 7156490.cif.'
_cod_database_code               7156490
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              7572