Dearomative 1,6-enyne cycloisomerization of alkyne-tethered benzofurans and indoles via a 6-endo-dig cyclization
Lu, Jin-Bo; Wang, Yi-Fan; Xu, Xue-Ting; Wang, Bing-Xia; Liang, Ren-Xiao; Jia, Yi-Xia; Chemical Communications 61 (2025) 7616–7619; doi:10.1039/D5CC00866B

data_7134414
_publ_section_title
;
 Dearomative 1,6-enyne cycloisomerization of alkyne-tethered benzofurans
 and indoles via a 6-endo-dig cyclization
;
_journal_issue                   42
_journal_name_full               'Chemical Communications'
_journal_page_first              7616
_journal_page_last               7619
_journal_paper_doi               10.1039/D5CC00866B
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C22 H21 N O2'
_chemical_formula_sum            'C22 H21 N O2'
_chemical_formula_weight         331.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-06
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-01-18 deposited with the CCDC.	2025-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 120.693(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.3399(15)
_cell_length_b                   12.3406(8)
_cell_length_c                   14.4440(10)
_cell_measurement_reflns_used    6391
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.496
_cell_measurement_theta_min      3.618
_cell_volume                     3730.8(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24039
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.643
_diffrn_reflns_theta_min         3.617
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0771 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.8876.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4271
_refine_ls_number_restraints     313
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0669
_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^)+(0.0682P)^2^+4.2821P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1765
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3350
_reflns_number_total             4271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00866b2.cif
_cod_data_source_block           230303_ljb_3_npr_0m
_cod_depositor_comments
'Adding full bibliography for 7134414--7134415.cif.'
_cod_database_code               7134414
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.942
_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. Restrained distances
 O1-C7 \\sim O1A-C7
 with sigma of 0.02
 O1-C6 \\sim O1A-C6A
 with sigma of 0.02
 C8-C7 \\sim C8A-C7
 with sigma of 0.02
 C8-C5 \\sim C8A-C5A
 with sigma of 0.02
 C6-C4 \\sim C6A-C4A
 with sigma of 0.04
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 C5-C6 \\sim C5A-C6A
 with sigma of 0.02
 C5-C4 \\sim C5A-C4A
 with sigma of 0.02
 C5-C3 \\sim C5A-C3A
 with sigma of 0.04
 C6-C1 \\sim C6A-C1A
 with sigma of 0.02
 C4-C2 \\sim C4A-C2A
 with sigma of 0.04
 C4-C3 \\sim C4A-C3A
 with sigma of 0.02
 C1-C2 \\sim C1A-C2A
 with sigma of 0.02
 C5-C1 \\sim C5A-C1A
 with sigma of 0.04
 C5-C9 \\sim C5A-C9A
 with sigma of 0.04
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C6-C2 \\sim C6A-C2A
 with sigma of 0.04
 O1-C5 \\sim O1A-C5A
 with sigma of 0.04
 O1-C1 \\sim O1A-C1A
 with sigma of 0.04
 C1-C3 \\sim C1A-C3A
 with sigma of 0.04
 C8-C6 \\sim C8A-C6A
 with sigma of 0.04
 C8-C4 \\sim C8A-C4A
 with sigma of 0.04
 C7-C5 \\sim C7-C5A
 with sigma of 0.04
 C7-C6 \\sim C7-C6A
 with sigma of 0.04
 C7-C9 \\sim C7-C9A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C7 \\sim C8 \\sim C9 \\sim O1A \\sim O1 \\sim C9A \\sim C8A \\sim C5 \\sim C6
\\sim C4 \\sim C1 \\sim C2 \\sim C3 \\sim C5A \\sim C4A \\sim C3A \\sim C2A
\\sim C1A \\sim C6A: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
4. Others
 Sof(O1A)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C8A)=Sof(C5A)=Sof(C4A)=Sof(H4A)=
 Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(H2A)=Sof(C1A)=Sof(H1A)=Sof(C6A)=1-FVAR(1)
 Sof(O1)=Sof(C8)=Sof(C5)=Sof(C6)=Sof(C4)=Sof(H4)=Sof(C1)=Sof(H1)=Sof(C2)=
 Sof(H2)=Sof(C3)=Sof(H3)=Sof(C9)=Sof(H9A)=Sof(H9B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C22(H22), C4(H4), C21(H21), C18(H18), C1(H1), C19(H19), C20(H20),
 C2(H2), C3(H3), C4A(H4A), C3A(H3A), C2A(H2A), C1A(H1A)
5.c Fitted hexagon refined as free rotating group:
 C5A(C4A,C3A,C2A,C1A,C6A)
5.d X=CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB)
5.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              22487
_shelx_hkl_checksum              75576
_shelx_fab_checksum              52305
_olex2_submission_special_instructions 'No special instructions were received'