Diastereoselective Construction of 2-Aminoindanones via an In(OTf)<sub>3</sub>-Catalyzed Domino Reaction.
Xing, Siyang; Xia, Hanyu; Guo, Junshuo; Zou, Chenchen; Gao, Tingxuan; Wang, Kui; Zhu, Bolin; Pei, Meiqi; Bai, Mengpei; The Journal of organic chemistry 84 (2019) 8984–8997; doi:10.1021/acs.joc.9b00876

data_4034161
_publ_section_title
;
 Diastereoselective Construction of 2-Aminoindanones via an
 In(OTf)<sub>3</sub>-Catalyzed Domino Reaction.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8984
_journal_page_last               8997
_journal_paper_doi               10.1021/acs.joc.9b00876
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C24 H27 N O7 S'
_chemical_formula_sum            'C24 H27 N O7 S'
_chemical_formula_weight         473.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                65.531(4)
_cell_angle_beta                 64.231(4)
_cell_angle_gamma                76.602(4)
_cell_formula_units_Z            2
_cell_length_a                   10.6851(4)
_cell_length_b                   11.3861(5)
_cell_length_c                   11.7403(5)
_cell_measurement_reflns_used    10206
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9090
_cell_measurement_theta_min      4.2720
_cell_volume                     1168.45(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w      0.00  25.00   1.00    1.00    --   38.00  91.00  84.55   25
  2  \w   -111.00  -7.00   1.00    1.00    --  -41.49 -19.00   0.00  104
  3  \w   -113.00 -59.00   1.00    1.00    --  -41.49 -57.00-120.00   54
  4  \w    -54.00 -13.00   1.00    1.00    --  -41.49 -57.00-120.00   41
  5  \w    -70.00 -18.00   1.00    1.00    --  -41.49 -38.00 -60.00   52
  6  \w     23.00  94.00   1.00    1.00    --   41.49-125.00 -90.00   71
  7  \w     24.00  87.00   1.00    1.00    --   41.49-125.00 120.00   63
  8  \w     12.00  39.00   1.00    1.00    --   46.00  83.00   7.60   27
  9  \w     12.00  37.00   1.00    1.00    --   46.00  83.00-158.22   25
 10  \w     18.00  45.00   1.00    1.00    --   50.00  82.00 153.04   27
 11  \w     18.00  43.00   1.00    1.00    --   50.00  80.00 -65.29   25
 12  \w     25.00  51.00   1.00    1.00    --   58.00  77.00-121.92   26
 13  \w     91.00 128.00   1.00    1.00    --   58.00  76.00  78.71   37
 14  \w     30.00  67.00   1.00    1.00    --   58.00  76.00  78.71   37
 15  \w     31.00  57.00   1.00    1.00    --   62.00  76.00 116.44   26
 16  \w     96.00 138.00   1.00    1.00    --   62.00  76.00 116.44   42
 17  \w     37.00  69.00   1.00    1.00    --   66.00  77.00 165.03   32
 18  \w    114.00 140.00   1.00    1.00    --   66.00  76.00-140.57   26
 19  \w     36.00  78.00   1.00    1.00    --   66.00  76.00 -66.48   42
 20  \w     34.00  68.00   1.00    1.00    --   66.00  76.00-140.57   34
 21  \w     82.00 142.00   1.00    1.00    --   66.00  76.00 -66.48   60
 22  \w     34.00  60.00   1.00    1.00    --   66.00  76.00  19.52   26
 23  \w    113.00 142.00   1.00    1.00    --   66.00  77.00 165.03   29
 24  \w     34.00  61.00   1.00    1.00    --   66.00  76.00  38.89   27
 25  \w     40.00  72.00   1.00    1.00    --   70.00  77.00-100.61   32
 26  \w     41.00  71.00   1.00    1.00    --   70.00  75.00 -26.77   30
 27  \w     44.00  78.00   1.00    1.00    --   74.00  76.00 124.70   34
 28  \w    125.00 150.00   1.00    1.00    --   74.00  76.00 124.70   25
 29  \w     48.00 113.00   1.00    3.82    --  107.08-125.00  90.00   65
 30  \w     80.00 173.00   1.00    3.82    --  107.08  61.00  60.00   93
 31  \w    122.00 176.00   1.00    3.82    --  107.08  77.00 150.00   54
 32  \w     75.00 101.00   1.00    3.82    --  107.08  77.00 150.00   26
 33  \w    113.00 161.00   1.00    3.82    --  107.08  45.00 -90.00   48
 34  \w     74.00 178.00   1.00    3.82    --  107.08  77.00 -60.00  104
 35  \w     82.00 109.00   1.00    3.82    --  107.08  45.00 -90.00   27
 36  \w     74.00 148.00   1.00    3.82    --  107.08  77.00-180.00   74
 37  \w     79.00 108.00   1.00    3.82    --  107.08  61.00 -90.00   29
 38  \w     34.00 110.00   1.00    3.82    --  107.08 -94.00 120.00   76
 39  \w    120.00 146.00   1.00    3.82    --  107.08  77.00 -30.00   26
 40  \w     74.00 142.00   1.00    3.82    --  107.08  77.00 120.00   68
 41  \w     74.00 100.00   1.00    3.82    --  107.08  77.00 -30.00   26
 42  \w     76.00 101.00   1.00    3.82    --  107.08  77.00  60.00   25
 43  \w     79.00 104.00   1.00    3.82    --  107.08  61.00 -60.00   25
 44  \w     74.00  99.00   1.00    3.82    --  107.08  77.00  30.00   25
 45  \w     78.00 114.00   1.00    3.82    --  107.08  61.00-180.00   36
 46  \w    151.00 177.00   1.00    3.82    --  107.08  61.00  30.00   26
 47  \w     75.00 174.00   1.00    3.82    --  107.08  77.00  90.00   99
 48  \w     79.00 117.00   1.00    3.82    --  107.08  61.00  30.00   38
 49  \w    112.00 177.00   1.00    3.82    --  107.08  77.00   0.00   65
 50  \w     74.00 100.00   1.00    3.82    --  107.08  77.00   0.00   26
 51  \w     39.00 116.00   1.00    3.82    --  107.08-125.00  30.00   77
 52  \w     74.00 100.00   1.00    3.82    --  107.08  77.00 -90.00   26
 53  \w    142.00 172.00   1.00    3.82    --  107.08  77.00 -90.00   30
 54  \w     74.00 177.00   1.00    3.82    --  107.08  77.00-150.00  103
 55  \w     78.00 149.00   1.00    3.82    --  107.08  61.00   0.00   71
 56  \w     39.00 137.00   1.00    3.82    --  107.08 -77.00-180.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0963357000
_diffrn_orient_matrix_UB_12      0.0619399000
_diffrn_orient_matrix_UB_13      0.1056406000
_diffrn_orient_matrix_UB_21      -0.0946192000
_diffrn_orient_matrix_UB_22      0.0627377000
_diffrn_orient_matrix_UB_23      -0.0809250000
_diffrn_orient_matrix_UB_31      -0.0866070000
_diffrn_orient_matrix_UB_32      -0.1200559000
_diffrn_orient_matrix_UB_33      0.0814868000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17070
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.275
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.617
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0523
_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^)+(0.1060P)^2^+0.2090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1572
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3632
_reflns_number_total             4158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00876_si_002.cif
_cod_data_source_block           a190227a
_cod_original_cell_volume        1168.44(10)
_cod_database_code               4034161
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C19A-C18 = C19-C18
 1.45 with sigma of 0.01
 C20A-C19A = C19-C20
 1.5 with sigma of 0.01
 N1-H1
 0.8 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.005
Uanis(C20) = Uanis(C20A)
Uanis(C19A) = Uanis(C19)
4. Others
 Sof(H18C)=Sof(H18D)=Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20D)=
 Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=
 Sof(H20C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C15(H15), C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C18(H18C,H18D), C22(H22A,H22B), C23(H23A,H23B), C19(H19A,
 H19B), C19A(H19C,H19D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13)
5.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-02-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.432
_oxdiff_exptl_absorpt_empirical_full_min 0.512