Site-selective synthesis of indanyl-substituted indole derivatives <i>via</i> 1,3-dithiane induced Nazarov cyclization.
Li, Jia; Li, Liang; Mao, Mingming; Li, Rui-Peng; Huo, Xing; Tang, Shouchu; Chemical communications (Cambridge, England) 60 (2024) 6540–6543; doi:10.1039/d4cc01963f

data_7133124
_publ_section_title
;
 Site-selective synthesis of indanyl-substituted indole derivatives
 <i>via</i> 1,3-dithiane induced Nazarov cyclization.
;
_journal_issue                   51
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6540
_journal_page_last               6543
_journal_paper_doi               10.1039/d4cc01963f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         '2(C23 H24 Br N O3 S2)'
_chemical_formula_sum            'C46 H48 Br2 N2 O6 S4'
_chemical_formula_weight         1012.92
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-08-31 deposited with the CCDC.	2024-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                114.8860(10)
_cell_angle_beta                 90.4100(10)
_cell_angle_gamma                117.9530(10)
_cell_formula_units_Z            2
_cell_length_a                   13.3806(2)
_cell_length_b                   13.8640(2)
_cell_length_c                   15.8118(2)
_cell_measurement_reflns_used    40543
_cell_measurement_temperature    302.74(10)
_cell_measurement_theta_max      75.9390
_cell_measurement_theta_min      3.1810
_cell_volume                     2272.67(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.74(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.955
_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    -82.00 -57.00   0.50    0.20    --  -46.45 133.00 178.00   50
  2  \w   -117.00 -72.00   0.50    0.20    --  -46.45-133.00 109.00   90
  3  \w   -113.00 -87.00   0.50    0.20    --  -46.45-136.00 -67.00   52
  4  \w    -65.00 -40.00   0.50    0.20    --  -46.45 136.00  -3.00   50
  5  \w     72.00 118.00   0.50    0.20    --   46.45 136.00  -3.00   92
  6  \w     52.00 100.00   0.50    0.20    --   46.45-136.00 -67.00   96
  7  \w     22.00  98.00   0.50    0.20    --   46.45-133.00 109.00  152
  8  \w   -120.00 -30.00   0.50    0.60    -- -102.00 136.00  -3.00  180
  9  \w   -145.00-120.00   0.50    0.60    -- -102.00-136.00 -67.00   50
 10  \w   -146.00-121.00   0.50    0.60    -- -102.00-133.00 109.00   50
 11  \w   -117.00 -31.00   0.50    0.60    -- -102.00 133.00 178.00  172
 12  \w     72.00 116.00   0.50    0.60    --  103.99-133.00 109.00   88
 13  \w     94.00 120.00   0.50    0.60    --  103.99-136.00 -67.00   52
 14  \w    121.00 146.00   0.50    0.60    --  103.99 136.00  -3.00   50
 15  \w    107.00 133.00   0.50    0.60    --  103.99 133.00 178.00   52
 16  \w    -21.00   5.00   0.50    0.20    --   14.00 103.00 118.79   52
 17  \w     -7.00  33.00   0.50    0.20    --   22.00  91.00 -27.65   80
 18  \w      2.00  33.00   0.50    0.20    --   26.00  82.00 100.20   62
 19  \w     13.00  38.00   0.50    0.20    --   42.00  90.00  39.62   50
 20  \w     12.00  37.00   0.50    0.20    --   42.00  92.00-131.68   50
 21  \w     16.00  41.00   0.50    0.20    --   42.00  85.00 112.74   50
 22  \w     35.00  88.00   0.50    0.20    --   46.45  37.00-120.00  106
 23  \w     83.00 118.00   0.50    0.20    --   46.45  77.00-150.00   70
 24  \w     25.00  60.00   0.50    0.20    --   46.45  77.00   0.00   70
 25  \w     35.00  68.00   0.50    0.20    --   46.45  19.00 120.00   66
 26  \w     24.00  50.00   0.50    0.20    --   46.45  77.00-150.00   52
 27  \w     83.00 109.00   0.50    0.20    --   50.00  75.00 -31.13   52
 28  \w     28.00  59.00   0.50    0.20    --   50.00  75.00 -31.13   62
 29  \w     33.00  61.00   0.50    0.20    --   54.00  74.00 121.35   56
 30  \w     33.00  70.00   0.50    0.20    --   54.00  76.00  73.81   74
 31  \w     31.00  56.00   0.50    0.20    --   54.00  77.00 157.17   50
 32  \w     33.00  59.00   0.50    0.20    --   54.00  73.00  65.65   52
 33  \w     35.00  68.00   0.50    0.20    --   58.00  77.00-124.16   66
 34  \w     36.00  62.00   0.50    0.20    --   58.00  76.00 -19.70   52
 35  \w     37.00  65.00   0.50    0.20    --   58.00  74.00-141.60   56
 36  \w     36.00  69.00   0.50    0.20    --   58.00  75.00  20.65   66
 37  \w     40.00  65.00   0.50    0.20    --   62.00  76.00 150.34   50
 38  \w     41.00  66.00   0.50    0.20    --   62.00  74.00 -82.89   50
 39  \w    -78.00 -45.00   0.50    0.20    --  -66.00 -72.00  22.30   66
 40  \w     43.00  68.00   0.50    0.20    --   66.00  77.00 -59.73   50
 41  \w     45.00  73.00   0.50    0.20    --   66.00  73.00 179.53   56
 42  \w     44.00  81.00   0.50    0.20    --   66.00  76.00 104.81   74
 43  \w     43.00  69.00   0.50    0.20    --   66.00  77.00-106.75   52
 44  \w    -81.00 -55.00   0.50    0.20    --  -74.00 -72.00  78.56   52
 45  \w    -79.00 -53.00   0.50    0.20    --  -74.00 -73.00   9.76   52
 46  \w    -77.00 -51.00   0.50    0.20    --  -74.00 -76.00  65.96   52
 47  \w    -90.00 -54.00   0.50    0.20    --  -74.00 -74.00 -50.25   72
 48  \w    -76.00 -51.00   0.50    0.20    --  -74.00 -77.00-155.83   50
 49  \w    -82.00 -56.00   0.50    0.20    --  -74.00 -64.00-160.58   52
 50  \w    -84.00 -57.00   0.50    0.60    --  -78.00 -72.00-105.39   54
 51  \w    -84.00 -58.00   0.50    0.60    --  -78.00 -69.00 -23.39   52
 52  \w    -94.00 -58.00   0.50    0.60    --  -78.00 -71.00  37.41   72
 53  \w    -83.00 -57.00   0.50    0.60    --  -78.00 -73.00   0.95   52
 54  \w   -101.00 -60.00   0.50    0.60    --  -82.00 -74.00 127.33   82
 55  \w    -92.00 -59.00   0.50    0.60    --  -82.00 -77.00 161.34   66
 56  \w    -88.00 -63.00   0.50    0.60    --  -82.00 -68.00-104.05   50
 57  \w   -101.00 -61.00   0.50    0.60    --  -82.00 -74.00 139.34   80
 58  \w   -152.00-127.00   0.50    0.60    --  -82.00 -74.00 -28.87   50
 59  \w    -96.00 -62.00   0.50    0.60    --  -82.00 -70.00 -69.80   68
 60  \w   -124.00 -60.00   0.50    0.60    --  -82.00 -74.00 -28.87  128
 61  \w    -89.00 -63.00   0.50    0.60    --  -82.00 -67.00  97.01   52
 62  \w    -91.00 -65.00   0.50    0.60    --  -86.00 -73.00  64.64   52
 63  \w    -91.00 -65.00   0.50    0.60    --  -86.00 -72.00 178.19   52
 64  \w   -100.00 -68.00   0.50    0.60    --  -90.00 -75.00 -33.35   64
 65  \w   -162.00-112.00   0.50    0.60    --  -90.00 -75.00 -33.35  100
 66  \w   -101.00 -69.00   0.50    0.60    --  -90.00 -72.00   3.45   64
 67  \w     68.00 102.00   0.50    0.60    --   90.00  75.00  70.43   68
 68  \w   -145.00-120.00   0.50    0.60    --  -90.00 -72.00   3.45   50
 69  \w   -102.00 -68.00   0.50    0.60    --  -90.00 -75.00-148.25   68
 70  \w   -134.00 -72.00   0.50    0.60    --  -90.00 -71.00  41.42  124
 71  \w   -154.00 -71.00   0.50    0.60    --  -90.00 -67.00  95.41  166
 72  \w   -109.00 -69.00   0.50    0.60    --  -90.00 -73.00 112.10   80
 73  \w   -161.00-118.00   0.50    0.60    --  -90.00 -75.00-148.25   86
 74  \w   -160.00-117.00   0.50    0.60    --  -90.00 -73.00 112.10   86
 75  \w   -102.00 -68.00   0.50    0.60    --  -90.00 -75.00-162.23   68
 76  \w   -153.00-127.00   0.50    0.60    --  -94.00 -75.00 134.03   52
 77  \w   -163.00 -75.00   0.50    0.60    --  -94.00 -67.00  14.26  176
 78  \w   -166.00 -79.00   0.50    0.60    --  -94.00 -66.00 144.05  174
 79  \w   -166.00 -76.00   0.50    0.60    --  -94.00 -70.00  82.93  180
 80  \w   -101.00 -75.00   0.50    0.60    --  -94.00 -68.00 -73.63   52
 81  \w   -167.00 -72.00   0.50    0.60    --  -94.00 -75.00-115.20  190
 82  \w   -116.00 -73.00   0.50    0.60    --  -94.00 -72.00  33.74   86
 83  \w   -104.00 -76.00   0.50    0.60    --  -94.00 -66.00-137.72   56
 84  \w   -167.00-120.00   0.50    0.60    --  -94.00 -66.00-137.72   94
 85  \w   -134.00 -77.00   0.50    0.60    --  -94.00 -66.00  48.63  114
 86  \w   -161.00-135.00   0.50    0.60    --  -94.00 -66.00  48.63   52
 87  \w    -98.00 -73.00   0.50    0.60    --  -94.00 -75.00 134.03   50
 88  \w   -169.00 -75.00   0.50    0.60    --  -98.00 -77.00  -6.90  188
 89  \w   -103.00 -77.00   0.50    0.60    --  -98.00 -76.00-172.19   52
 90  \w   -153.00-108.00   0.50    0.60    --  -98.00 -76.00-172.19   90
 91  \w   -106.00 -81.00   0.50    0.60    -- -102.00 -76.00 -19.88   50
 92  \w   -175.00-130.00   0.50    0.60    -- -102.00 -76.00 -19.88   90
 93  \w   -169.00 -82.00   0.50    0.60    -- -102.00 -69.00-104.56  174
 94  \w   -158.00 -80.00   0.50    0.60    -- -102.00 -74.00 161.77  156
 95  \w   -135.00 -85.00   0.50    0.60    -- -102.00 -69.00 -73.42  100
 96  \w   -110.00 -82.00   0.50    0.60    -- -102.00 -70.00 -44.65   56
 97  \w   -164.00-127.00   0.50    0.60    -- -102.00 -70.00 -44.65   74
 98  \w   -111.00 -86.00   0.50    0.60    -- -102.00 -68.00 -54.59   50
 99  \w   -175.00-149.00   0.50    0.60    -- -102.00 -68.00 -54.59   52
100  \w    -59.00 -33.00   0.50    0.60    -- -102.00 135.00 112.02   52
101  \w   -119.00 -71.00   0.50    0.60    -- -102.00 135.00 112.02   96
102  \w   -108.00 -42.00   0.50    0.60    -- -102.00 109.00 -98.14  132
103  \w   -148.00 -79.00   0.50    0.60    -- -102.00 -77.00-180.00  138
104  \w   -135.00 -81.00   0.50    0.60    -- -102.00 -72.00 -85.15  108
105  \w     43.00  72.00   0.50    0.60    --  103.99 -61.00-120.00   58
106  \w     34.00 108.00   0.50    0.60    --  103.99-125.00   0.00  148
107  \w     36.00 102.00   0.50    0.60    --  103.99 -94.00   0.00  132
108  \w     40.00  99.00   0.50    0.60    --  103.99 -94.00 150.00  118
109  \w     37.00  73.00   0.50    0.60    --  103.99 -61.00 150.00   72
110  \w     40.00  67.00   0.50    0.60    --  103.99 -61.00 120.00   54
111  \w    116.00 170.00   0.50    0.60    --  103.99  77.00 -30.00  108
112  \w     83.00 111.00   0.50    0.60    --  103.99-125.00 -30.00   56
113  \w     41.00  91.00   0.50    0.60    --  103.99 -94.00  90.00  100
114  \w     39.00  70.00   0.50    0.60    --  103.99 -61.00 -30.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0077492000
_diffrn_orient_matrix_UB_12      -0.1164704000
_diffrn_orient_matrix_UB_13      -0.0042966000
_diffrn_orient_matrix_UB_21      0.1073661000
_diffrn_orient_matrix_UB_22      0.0836550000
_diffrn_orient_matrix_UB_23      0.0871831000
_diffrn_orient_matrix_UB_31      -0.0811418000
_diffrn_orient_matrix_UB_32      -0.0020946000
_diffrn_orient_matrix_UB_33      0.0686954000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            74877
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.296
_diffrn_reflns_theta_min         3.186
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.384
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.789
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00027(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     548
_refine_ls_number_reflns         9090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+1.2331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8066
_reflns_number_total             9090
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01963f2.cif
_cod_data_source_block           lijia_0427_3_auto
_cod_depositor_comments          'Adding full bibliography for 7133124.cif.'
_cod_original_cell_volume        2272.66(6)
_cod_database_code               7133124
_shelx_shelxl_version_number     2018/1
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C33(H33A,
 H33B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C17(H17), N2(H2A), C25(H25), C26(H26),
  C27(H27), C30(H30), C40(H40)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C44(H44A,H44B,
 H44C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              96789
_shelx_hkl_checksum              13080
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.804
_oxdiff_exptl_absorpt_empirical_full_min 0.307