Transition-metal-free intramolecular double hydrofunctionalization of alkyne to access 6/7/5-fused heterocyclic skeletons.
Aghaie, Kimia; Amiri, Kamran; Rezaei-Gohar, Mohammad; Rominger, Frank; Dar'in, Dmitry; Sapegin, Alexander; Balalaie, Saeed; Chemical communications (Cambridge, England) 60 (2024) 2661–2664; doi:10.1039/d3cc05724k

data_7132679
_publ_section_title
;
 Transition-metal-free intramolecular double hydrofunctionalization of
 alkyne to access 6/7/5-fused heterocyclic skeletons.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2661
_journal_page_last               2664
_journal_paper_doi               10.1039/d3cc05724k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C23 H18 Br N3 O2'
_chemical_formula_weight         448.31
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-08-30 deposited with the CCDC.	2024-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.3335(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8608(5)
_cell_length_b                   18.2829(12)
_cell_length_c                   13.4885(9)
_cell_measurement_reflns_used    6393
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.23
_cell_volume                     1926.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.272
_diffrn_reflns_theta_min         1.884
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    2.159
_exptl_absorpt_correction_T_max  0.8496
_exptl_absorpt_correction_T_min  0.7695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       brick
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0294P)^2^+0.8234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3754
_reflns_number_total             4871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05724k2.cif
_cod_data_source_block           sba197
_cod_depositor_comments
'Adding full bibliography for 7132679--7132680.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7132679
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.788
_shelx_estimated_absorpt_t_max   0.828
_shelx_res_checksum              44058
_shelx_hkl_checksum              16690