Lewis/Brønsted acid-mediated cyclization/amidation of 1,6-enynes with nitriles: access to 3-enamide substituted dihydrobenzofurans.
Chen, Zan; Huang, Wenting; Su, Yu; Jiang, Huanfeng; Wu, Wanqing; Chemical communications (Cambridge, England) 59 (2023) 4523–4526; doi:10.1039/d3cc00787a

data_7131488
_publ_section_title
;
 Lewis/Br&#xf8;nsted acid-mediated cyclization/amidation of 1,6-enynes
 with nitriles: access to 3-enamide substituted dihydrobenzofurans.
;
_journal_issue                   30
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4523
_journal_page_last               4526
_journal_paper_doi               10.1039/d3cc00787a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C19 H16 F3 N O2'
_chemical_formula_sum            'C19 H16 F3 N O2'
_chemical_formula_weight         347.33
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-26 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.050(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.843(7)
_cell_length_b                   9.345(4)
_cell_length_c                   9.737(4)
_cell_measurement_reflns_used    1516
_cell_measurement_temperature    170
_cell_measurement_theta_max      22.732
_cell_measurement_theta_min      2.434
_cell_volume                     1707.9(12)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      170
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13067
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.105
_diffrn_reflns_theta_max         25.105
_diffrn_reflns_theta_min         2.170
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0966 before and 0.0652 after correction. The Ratio of minimum to maximum transmission is 0.8671. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     334
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0613
_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^)+(0.0540P)^2^+0.9589P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1570
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1730
_reflns_number_total             2960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00787a2.cif
_cod_data_source_block           cz2
_cod_depositor_comments
'Adding full bibliography for 7131488--7131489.cif.'
_cod_database_code               7131488
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(F2) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F5) \\sim
Ueq, Uanis(F4) \\sim Ueq, Uanis(F3) \\sim Ueq: with sigma of 0.005 and sigma
for terminal atoms of 0.01
4. Others
 Fixed Sof: F1(0.75) F5(0.75) F3(0.75) F4(0.25) F6(0.25) F2(0.25)
5.a Ternary CH refined with riding coordinates:
 C1(H1A)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C14(H14), C15(H15), C18(H18), C17(H17), C6(H6), C7(H7), C8(H8)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C2(H2A,H2B,H2C)
;
_olex2_submission_special_instructions 'No special instructions were received'