Cascade hydroarylation/Diels-Alder cycloaddition of alkynylindoles with electron-deficient alkynes and alkenes.
Feng, Guang-Chao; Li, Jun-Chi; Huang, Xiang; Liu, Ji-Kai; Wu, Bin; Yang, Jin-Ming; Chemical communications (Cambridge, England) 60 (2024) 328–331; doi:10.1039/d3cc05210a

data_7132423
_publ_section_title
;
 Cascade hydroarylation/Diels-Alder cycloaddition of alkynylindoles with
 electron-deficient alkynes and alkenes.
;
_journal_issue                   3
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              328
_journal_page_last               331
_journal_paper_doi               10.1039/d3cc05210a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C30 H25 Br2 N3 O4 S'
_chemical_formula_sum            'C30 H25 Br2 N3 O4 S'
_chemical_formula_weight         683.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-24
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-07-12 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.922(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.8975(8)
_cell_length_b                   9.0370(2)
_cell_length_c                   31.2449(14)
_cell_measurement_reflns_used    4674
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      73.5550
_cell_measurement_theta_min      4.4260
_cell_volume                     5581.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_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    -64.00  24.00   1.00    2.00    --  -40.98  37.00  30.00   88
  2  \w     34.00  94.00   1.00    2.00    --   40.98-125.00  90.00   60
  3  \w     71.00  97.00   1.00    5.00    --  107.58 -94.00 -30.00   26
  4  \w     90.00 134.00   1.00    5.00    --  107.58-149.00 -50.00   44
  5  \w     52.00  95.00   1.00    2.00    --   40.98-125.00 -60.00   43
  6  \w     45.00 104.00   1.00    5.00    --  107.58 -94.00  30.00   59
  7  \w     48.00 115.00   1.00    5.00    --  107.58 -45.00   0.00   67
  8  \w     79.00 178.00   1.00    5.00    --  107.58  30.00  60.00   99
  9  \w    153.00 178.00   1.00    5.00    --  107.58 125.00 -90.00   25
 10  \w    146.00 177.00   1.00    5.00    --  107.58 125.00-120.00   31
 11  \w     94.00 120.00   1.00    5.00    --  107.58 125.00 -90.00   26
 12  \w     94.00 123.00   1.00    5.00    --  107.58 125.00 -60.00   29
 13  \w     97.00 129.00   1.00    5.00    --  107.58 125.00-120.00   32
 14  \w     94.00 175.00   1.00    5.00    --  107.58 125.00 -30.00   81
 15  \w     58.00  84.00   1.00    5.00    --  107.58 -30.00 150.00   26
 16  \w     36.00 102.00   1.00    5.00    --  107.58 -45.00  90.00   66
 17  \w     31.00 121.00   1.00    5.00    --  107.58 -30.00-120.00   90
 18  \w     34.00 130.00   1.00    5.00    --  107.58 -77.00-120.00   96
 19  \w    -99.00 -73.00   1.00    2.00    --  -40.98-149.00 -50.00   26
 20  \w   -113.00 -17.00   1.00    2.00    --  -40.98 -37.00-150.00   96
 21  \w   -115.00 -24.00   1.00    2.00    --  -40.98 -37.00 120.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0320911500
_diffrn_orient_matrix_UB_12      -0.0152683500
_diffrn_orient_matrix_UB_13      -0.0377623500
_diffrn_orient_matrix_UB_21      -0.0708609500
_diffrn_orient_matrix_UB_22      0.0050118500
_diffrn_orient_matrix_UB_23      -0.0358637500
_diffrn_orient_matrix_UB_31      0.0050048500
_diffrn_orient_matrix_UB_32      0.1696382500
_diffrn_orient_matrix_UB_33      -0.0023672500
_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  0.1078
_diffrn_reflns_av_unetI/netI     0.1047
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            18816
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.884
_diffrn_reflns_theta_min         2.990
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_description       block
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0484P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4015
_reflns_number_total             5534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05210a2.cif
_cod_data_source_block           f678
_cod_depositor_comments          'Adding full bibliography for 7132423.cif.'
_cod_database_code               7132423
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C20(H20), C21(H21), C22(H22), C25(H25),
 C26(H26), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_shelx_res_checksum              52149
_shelx_hkl_checksum              80418
_olex2_date_sample_data_collection 2023-04-23
_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 2.195
_oxdiff_exptl_absorpt_empirical_full_min 0.361