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_7226980
_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_formula_sum            'C27 H29 N O3 S'
_chemical_formula_weight         447.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-05-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.732(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.477(5)
_cell_length_b                   19.264(8)
_cell_length_c                   21.970(9)
_cell_measurement_reflns_used    967
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.442
_cell_measurement_theta_min      2.583
_cell_volume                     4857(4)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_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  0.0437
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23754
_diffrn_reflns_point_group_measured_fraction_full 0.874
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         1.406
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1165
_refine_ls_number_reflns         17711
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      0.878
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0672P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_full    0.742
_reflns_Friedel_fraction_max     0.679
_reflns_number_gt                10757
_reflns_number_total             17711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra19916j2.cif
_cod_data_source_block           a60114a
_cod_original_cell_volume        4857(3)
_cod_database_code               7226980
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.953
_shelxl_version_number           2013-2
_shelx_res_checksum              33127