Palladium-catalyzed ligand-regulated divergent synthesis of pyrrole[2,3-<i>b</i>]indoles and ureas from 2-ethynylanilines and isocyanides.
Zhang, Min; Zheng, Yongpeng; Jin, Yangbin; Jiang, Huanfeng; Wu, Wanqing; Chemical communications (Cambridge, England) 60 (2024) 2950–2953; doi:10.1039/d3cc05387c

data_7132740
_publ_section_title
;
 Palladium-catalyzed ligand-regulated divergent synthesis of
 pyrrole[2,3-<i>b</i>]indoles and ureas from 2-ethynylanilines and
 isocyanides.
;
_journal_issue                   21
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2950
_journal_page_last               2953
_journal_paper_doi               10.1039/d3cc05387c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C19 H20 N2 O'
_chemical_formula_sum            'C19 H20 N2 O'
_chemical_formula_weight         292.37
_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             2023-03-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-14 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.679(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.637(3)
_cell_length_b                   13.293(4)
_cell_length_c                   29.631(8)
_cell_measurement_reflns_used    2254
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.931
_cell_measurement_theta_min      2.580
_cell_volume                     3378.9(18)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.992
_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  0.1175
_diffrn_reflns_av_unetI/netI     0.1246
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            23319
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_min         2.065
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1453 before and 0.0702 after correction.
The Ratio of minimum to maximum transmission is 0.7833.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1894
_refine_ls_R_factor_gt           0.0726
_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^)+(0.0617P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3002
_reflns_number_total             6847
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05387c2.cif
_cod_data_source_block           zm1211_0m
_cod_depositor_comments
'Adding full bibliography for 7132740--7132741.cif.'
_cod_original_cell_volume        3378.8(17)
_cod_database_code               7132740
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.992
_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 Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), N3(H3), N4(H4), C24(H24), C13(H13), C32(H32), C23(H23),
 C1(H1A), C20(H20), C22(H22), C5(H5), C10(H10), C21(H21), C4(H4A), C12(H12),
 C2(H2A), C31(H31), C11(H11), C3(H3A), C30(H30), C29(H29)
2.b Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C38(H38A,H38B,
 H38C), C37(H37A,H37B,H37C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              25447
_shelx_hkl_checksum              27180
_olex2_submission_special_instructions 'No special instructions were received'