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_7130443
_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         'C26 H26 N2 O2 S'
_chemical_formula_sum            'C26 H26 N2 O2 S'
_chemical_formula_weight         430.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-02
_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                90
_cell_angle_beta                 92.7640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.55350(10)
_cell_length_b                   11.41710(10)
_cell_length_c                   18.3424(2)
_cell_measurement_reflns_used    8912
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      71.4490
_cell_measurement_theta_min      3.8830
_cell_volume                     2207.51(4)
_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      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_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     80.00 132.00   0.50    0.50    --   42.30  77.00 -90.00  104
  2  \w    -31.00  22.00   0.50    0.50    --   42.30 -82.00 -30.00  106
  3  \w    -44.00  64.00   0.50    0.50    --   42.30 -38.00-180.00  216
  4  \w     82.00 123.00   0.50    0.50    --   42.30  77.00-120.00   82
  5  \w     61.00  86.00   0.50    0.50    --   42.30 -82.00 -30.00   50
  6  \w    118.00 158.00   0.50    0.50    --  101.60  50.00-150.00   80
  7  \w     80.00 155.00   0.50    0.50    --  101.60  77.00-150.00  150
  8  \w    151.00 191.00   0.50    0.50    --  101.60  82.00-120.00   80
  9  \w    159.00 186.00   0.50    0.50    --  101.60  82.00 -90.00   54
 10  \w    156.00 191.00   0.50    0.50    --  101.60  50.00 -30.00   70
 11  \w     22.00 121.00   0.50    0.50    --  101.60 -77.00-120.00  198
 12  \w     70.00  95.00   0.50    0.50    --  101.60  50.00-150.00   50
 13  \w     87.00 120.00   0.50    0.50    --  101.60  82.00 -90.00   66
 14  \w     13.00 133.00   0.50    0.50    --  101.60 -50.00 -30.00  240
 15  \w    103.00 129.00   0.50    0.50    --  101.60 -63.00-120.00   52
 16  \w     28.00  68.00   0.50    0.50    --  101.60 -63.00-120.00   80
 17  \w     92.00 117.00   0.50    0.50    --  101.60  82.00  30.00   50
 18  \w     91.00 150.00   0.50    0.50    --  101.60  50.00 -30.00  118
 19  \w    110.00 137.00   0.50    0.50    --  101.60  82.00-120.00   54
;
_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      -0.0558089000
_diffrn_orient_matrix_UB_12      -0.0460925000
_diffrn_orient_matrix_UB_13      0.0705883000
_diffrn_orient_matrix_UB_21      -0.0839911000
_diffrn_orient_matrix_UB_22      -0.0864319000
_diffrn_orient_matrix_UB_23      -0.0451074000
_diffrn_orient_matrix_UB_31      0.1056235000
_diffrn_orient_matrix_UB_32      -0.0930122000
_diffrn_orient_matrix_UB_33      0.0069958000
_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  0.0141
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11203
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.576
_diffrn_reflns_theta_min         4.194
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.500
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64892
_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    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0036(2)
_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   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0473P)^2^+0.6233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4049
_reflns_number_total             4219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02840a2.cif
_cod_data_source_block           5k
_cod_database_code               7130443
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_usercomment     'C H O N S'
_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:
 C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              76636
_shelx_hkl_checksum              3081
_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 1.676
_oxdiff_exptl_absorpt_empirical_full_min 0.629