Pd-catalyzed domino Heck cyclization/cross-coupling of indoles with β-chlorovinyl ketones: synthesis of furan-bearing indolo[2,1-<i>α</i>]isoquinolines with antifungal activity.
Bai, Yongqi; Qi, Xingrui; Li, Hanjing; Ban, Yihui; Zhao, Rong; Wang, Yian; Zhang, Jingli; Sun, Taolei; Gao, Guanbin; Organic & biomolecular chemistry 23 (2025) 3307–3313; doi:10.1039/d5ob00165j

data_7160473
_publ_section_title
;
 Pd-catalyzed domino Heck cyclization/cross-coupling of indoles with
 &#x3b2;-chlorovinyl ketones: synthesis of furan-bearing
 indolo[2,1-<i>&#x3b1;</i>]isoquinolines with antifungal activity.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3307
_journal_page_last               3313
_journal_paper_doi               10.1039/d5ob00165j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C32 H28 Br N O2'
_chemical_formula_weight         538.46
_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
;
2024-12-23 deposited with the CCDC.	2025-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.855(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8884(10)
_cell_length_b                   9.8535(8)
_cell_length_c                   21.4916(18)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      61.40
_cell_measurement_theta_min      3.58
_cell_volume                     2514.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_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, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            30775
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         61.700
_diffrn_reflns_theta_min         3.583
_exptl_absorpt_coefficient_mu    1.620
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0054(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0443P)^2^+2.1929P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5654
_reflns_number_total             5861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00165j2.cif
_cod_data_source_block           240514h_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160473
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.707
_shelx_estimated_absorpt_t_max   0.829
_shelx_res_checksum              59955