Metal-free dearomative [5+2]/[2+2] cycloaddition of 1<i>H</i>-indoles with <i>ortho</i>-(trimethylsilyl)aryl triflates.
Chen, Xinyu; Yang, Na; Zeng, Wen; Wang, Lei; Li, Pinhua; Li, Hongji; Chemical communications (Cambridge, England) 57 (2021) 7047–7050; doi:10.1039/d1cc02550c

data_7128523
_publ_section_title
;
 Metal-free dearomative [5+2]/[2+2] cycloaddition of 1<i>H</i>-indoles
 with <i>ortho</i>-(trimethylsilyl)aryl triflates.
;
_journal_issue                   57
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7047
_journal_page_last               7050
_journal_paper_doi               10.1039/d1cc02550c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C27 H21 N'
_chemical_formula_sum            'C27 H21 N'
_chemical_formula_weight         359.45
_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             2020-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-19 deposited with the CCDC.	2021-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                67.411(2)
_cell_angle_beta                 86.553(2)
_cell_angle_gamma                87.881(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0099(13)
_cell_length_b                   10.3660(15)
_cell_length_c                   11.4985(16)
_cell_measurement_reflns_used    1543
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.42
_cell_measurement_theta_min      2.90
_cell_volume                     989.6(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6052
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.735
_diffrn_reflns_theta_min         2.128
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6558
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0515 before and 0.0265 after correction.
The Ratio of minimum to maximum transmission is 0.8796.
The \l/2 correction factor is 0.00150.
;
_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    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0582
_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^)+(0.0767P)^2^+0.1995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1679
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2652
_reflns_number_total             4351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02550c2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7128523--7128524.cif.'
_cod_database_code               7128523
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              54859
_shelx_hkl_checksum              75101
_olex2_submission_special_instructions 'No special instructions were received'