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_7131489
_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         'C18 H15 Br2 N O2'
_chemical_formula_sum            'C18 H15 Br2 N O2'
_chemical_formula_weight         437.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-31
_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                 92.437(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1676(10)
_cell_length_b                   4.8980(6)
_cell_length_c                   19.342(2)
_cell_measurement_reflns_used    2390
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.776
_cell_measurement_theta_min      2.998
_cell_volume                     867.73(17)
_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      170.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4773
_diffrn_reflns_point_group_measured_fraction_full 0.792
_diffrn_reflns_point_group_measured_fraction_max 0.769
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         2.108
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.679
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0812 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.7389. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 707 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2713
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0359
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.559
_reflns_Friedel_fraction_full    0.593
_reflns_Friedel_fraction_max     0.553
_reflns_number_gt                2218
_reflns_number_total             2713
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00787a2.cif
_cod_data_source_block           cz5_0m
_cod_depositor_comments
'Adding full bibliography for 7131488--7131489.cif.'
_cod_original_cell_volume        867.74(17)
_cod_database_code               7131489
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.800
_shelx_estimated_absorpt_t_min   0.470
_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.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C1(H1A), C2(H2), C5(H5), C4(H4), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'