PyBidine-Ni(OAc)<sub>2</sub>-Catalyzed Michael/Aldol Reaction of Methyleneindolinones and Thiosalicylaldehydes for Stereochemically Divergent Thiochromanyl-spirooxindoles.
Arai, Takayoshi; Miyazaki, Tomoya; Ogawa, Hiroki; Masu, Hyuma; Organic letters 18 (2016) 5824–5827; doi:10.1021/acs.orglett.6b02783

data_1555868
_publ_section_title
;
 PyBidine-Ni(OAc)<sub>2</sub>-Catalyzed Michael/Aldol Reaction of
 Methyleneindolinones and Thiosalicylaldehydes for Stereochemically
 Divergent Thiochromanyl-spirooxindoles.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5824
_journal_page_last               5827
_journal_paper_doi               10.1021/acs.orglett.6b02783
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         '4(C22 H16 Br N O2 S), 2.5(C H2 Cl2) '
_chemical_formula_sum            'C90.5 H69 Br4 Cl5 N4 O8 S4'
_chemical_formula_weight         1965.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.4233(13)
_cell_length_b                   28.5691(18)
_cell_length_c                   33.289(2)
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.9108
_cell_measurement_theta_min      2.2071
_cell_volume                     19423(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            48400
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.367
_diffrn_reflns_theta_min         1.223
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.933
_exptl_absorpt_correction_T_max  0.45
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             7944
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         1.653
_refine_diff_density_min         -1.258
_refine_ls_abs_structure_details
;
Flack x determined using 4793 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1055
_refine_ls_number_reflns         17721
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0862P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                12795
_reflns_number_total             17721
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02783_si_002.cif
_cod_data_source_block           I
_cod_original_cell_volume        19423.(2)
_cod_original_formula_sum        'C90.50 H69 Br4 Cl5 N4 O8 S4'
_cod_database_code               1555868
_shelx_res_checksum              46677
_shelx_hkl_checksum              65611