Remote Stereocontrolled Asymmetric 1,6-Addition/1,4-Addition Cascade Reactions between Cyclic Dienones and 2-Indolinethiones
Sun, Xiaohua; Fei, Jie; Zou, Chuncheng; Lu, Min; Ye, Jinxing; RSC Adv.  (2016) –; doi:10.1039/C6RA19916J

data_7226982
_publ_section_title
;
 Remote Stereocontrolled Asymmetric 1,6-Addition/1,4-Addition Cascade
 Reactions between Cyclic Dienones and 2-Indolinethiones
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA19916J
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H21 N O3 S'
_chemical_formula_weight         343.43
_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   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-07-22 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8324(19)
_cell_length_b                   10.981(3)
_cell_length_c                   20.695(5)
_cell_measurement_reflns_used    2566
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      44.133
_cell_measurement_theta_min      5.410
_cell_volume                     1779.9(8)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10113
_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         25.493
_diffrn_reflns_theta_min         1.968
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
; 
 Flack x determined using 1064 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0590P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2838
_reflns_number_total             3313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra19916j2.cif
_cod_data_source_block           cd16448
_cod_original_cell_volume        1779.8(7)
_cod_database_code               7226982
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2013-4
_shelx_res_checksum              36182