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_7134415
_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         'C28 H30 N2 O2'
_chemical_formula_sum            'C28 H30 N2 O2'
_chemical_formula_weight         426.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-01-18 deposited with the CCDC.	2025-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.031(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3912(6)
_cell_length_b                   11.2049(6)
_cell_length_c                   16.6414(9)
_cell_measurement_reflns_used    9778
_cell_measurement_temperature    169(2)
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      3.95
_cell_volume                     2310.2(2)
_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 (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      169.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30611
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.381
_diffrn_reflns_theta_min         4.488
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1744 before and 0.1045 after correction.
The Ratio of minimum to maximum transmission is 0.5744.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0547P)^2^+0.5237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3920
_reflns_number_total             4227
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00866b2.cif
_cod_data_source_block           cu_220705_ljb_pd_c_0m
_cod_depositor_comments
'Adding full bibliography for 7134414--7134415.cif.'
_cod_database_code               7134415
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.773
_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:
 C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C23(H23), C24(H24), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              31260
_shelx_hkl_checksum              1929
_olex2_submission_special_instructions 'No special instructions were received'