Acid-promoted intra- and intermolecular [2+2] cycloaddition of indoles to aryl alkynes to access cyclobutene-fused indolines
Wang, Qing; Wang, Sen-Lin; Fan, Jin-Bao; Zeng, Guang-Yao; Zhou, Ying-Jun; Deng, Xu; Chemical Communications  (2022) –; doi:10.1039/D2CC02840A

data_7130442
_publ_section_title
;
 Acid-promoted intra- and intermolecular [2+2] cycloaddition of indoles to
 aryl alkynes to access cyclobutene-fused indolines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02840A
_journal_year                    2022
_chemical_formula_moiety         'C20 H19 N'
_chemical_formula_sum            'C20 H19 N'
_chemical_formula_weight         273.36
_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             2022-04-23
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-05-18 deposited with the CCDC.	2022-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                107.989(2)
_cell_angle_beta                 94.9730(10)
_cell_angle_gamma                92.730(2)
_cell_formula_units_Z            2
_cell_length_a                   8.71530(10)
_cell_length_b                   9.2902(2)
_cell_length_c                   9.50980(10)
_cell_measurement_reflns_used    5445
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.5540
_cell_measurement_theta_min      4.9250
_cell_volume                     727.33(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.958
_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     56.00  82.00   0.50    0.50    --   42.30 -77.00-150.00   52
  2  \w     85.00 110.00   0.50    0.50    --   42.30  77.00 120.00   50
  3  \w     23.00  57.00   0.50    0.50    --   42.30 -57.00   0.00   68
  4  \w     83.00 126.00   0.50    0.50    --   42.30  77.00 -60.00   86
  5  \w    -24.00  82.00   0.50    0.50    --   42.30 -82.00 150.00  212
  6  \w     42.00  83.00   0.50    0.50    --   42.30 -82.00 -60.00   82
  7  \w    -41.00  37.00   0.50    0.50    --   42.30 -77.00-150.00  156
  8  \w    -31.00  38.00   0.50    0.50    --   42.30 -82.00 -60.00  138
  9  \w     82.00 132.00   0.50    0.50    --   42.30  77.00-150.00  100
 10  \w     60.00 146.00   0.50    0.50    --  102.30 -82.00-120.00  172
 11  \w     19.00  44.00   0.50    0.50    --  102.30 -82.00-120.00   50
 12  \w     50.00  94.00   0.50    0.50    --  102.30 -82.00  30.00   88
 13  \w     76.00 146.00   0.50    0.50    --  102.30 -82.00  60.00  140
 14  \w    110.00 146.00   0.50    0.50    --  102.30  82.00 -60.00   72
 15  \w     13.00  96.00   0.50    0.50    --  102.30 -63.00-150.00  166
 16  \w     16.00  41.00   0.50    0.50    --  102.30 -82.00 -60.00   50
 17  \w     77.00 106.00   0.50    0.50    --  102.30 -82.00 120.00   58
 18  \w     14.00 133.00   0.50    0.50    --  102.30 -63.00  30.00  238
 19  \w     27.00  52.00   0.50    0.50    --  102.30 -82.00 120.00   50
 20  \w     68.00 172.00   0.50    0.50    --  102.30 -12.00 -60.00  208
 21  \w     13.00  63.00   0.50    0.50    --  102.30 -12.00 -60.00  100
 22  \w     86.00 122.00   0.50    0.50    --  102.30 -82.00 -60.00   72
 23  \w     14.00 184.00   0.50    0.50    --  102.30  12.00   0.00  340
 24  \w     99.00 134.00   0.50    0.50    --  102.30 -63.00-150.00   70
 25  \w    165.00 190.00   0.50    0.50    --  102.30  82.00  90.00   50
 26  \w     43.00 103.00   0.50    0.50    --  102.30 -82.00-180.00  120
 27  \w     67.00 141.00   0.50    0.50    --  102.30 -38.00  30.00  148
 28  \w     98.00 124.00   0.50    0.50    --  102.30 -82.00  90.00   52
 29  \w     30.00  55.00   0.50    0.50    --  102.30 -38.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1565372000
_diffrn_orient_matrix_UB_12      0.0009949000
_diffrn_orient_matrix_UB_13      -0.0636651000
_diffrn_orient_matrix_UB_21      0.0711161000
_diffrn_orient_matrix_UB_22      -0.0711680000
_diffrn_orient_matrix_UB_23      0.1144880000
_diffrn_orient_matrix_UB_31      -0.0460053000
_diffrn_orient_matrix_UB_32      -0.1597509000
_diffrn_orient_matrix_UB_33      -0.1103793000
_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  0.0122
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6281
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.998
_diffrn_reflns_theta_min         4.918
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0218(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0473P)^2^+0.2390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2617
_reflns_number_total             2750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02840a2.cif
_cod_data_source_block           8
_cod_database_code               7130442
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.928
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              25020
_shelx_hkl_checksum              10026
_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 1.557
_oxdiff_exptl_absorpt_empirical_full_min 0.628