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_7132741
_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         'C26 H28 N4'
_chemical_formula_sum            'C26 H28 N4'
_chemical_formula_weight         396.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-09-14 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.8280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.2301(4)
_cell_length_b                   10.2357(3)
_cell_length_c                   28.4109(8)
_cell_measurement_reflns_used    8678
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.361
_cell_measurement_theta_min      2.401
_cell_volume                     4406.1(2)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0420
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            24779
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.401
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0740 before and 0.0482 after correction. The Ratio of minimum to maximum transmission is 0.9532. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0470P)^2^+3.6867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3536
_reflns_number_total             4510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05387c2.cif
_cod_data_source_block           124zm1201_0m
_cod_depositor_comments
'Adding full bibliography for 7132740--7132741.cif.'
_cod_database_code               7132741
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.991
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C3(H3), C15(H15), C2(H2), C18(H18), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C25(H25A,H25B,H25C), C22(H22A,H22B,H22C), C26(H26A,H26B,
 H26C), C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'