Palladium-catalyzed oxidative C–H activation/annulation of N-alkylanilines with bromoalkynes: access to functionalized 3-bromoindoles
Fang, Songjia; Chen, Wenhao; Jiang, Huanfeng; Ma, Ruize; Wu, Wanqing; Chemical Communications  (2022) –; doi:10.1039/D2CC03298H

data_7130508
_publ_section_title
;
 Palladium-catalyzed oxidative C--H activation/annulation of
 N-alkylanilines with bromoalkynes: access to functionalized
 3-bromoindoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03298H
_journal_year                    2022
_chemical_formula_moiety         'C17 H16 Br N'
_chemical_formula_sum            'C17 H16 Br N'
_chemical_formula_weight         314.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-16 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                74.380(4)
_cell_angle_beta                 87.105(4)
_cell_angle_gamma                78.928(3)
_cell_formula_units_Z            4
_cell_length_a                   8.8179(11)
_cell_length_b                   9.8490(11)
_cell_length_c                   17.496(2)
_cell_measurement_reflns_used    2782
_cell_measurement_temperature    170
_cell_measurement_theta_max      23.620
_cell_measurement_theta_min      2.417
_cell_volume                     1436.1(3)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_unetI/netI     0.1048
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14912
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         2.185
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.848
_exptl_absorpt_correction_T_max  0.2603
_exptl_absorpt_correction_T_min  0.2046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1108 before and 0.0656 after correction. The Ratio of minimum to maximum transmission is 0.7860. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.0743
_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^)+(0.0681P)^2^+14.3596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.2215
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3176
_reflns_number_total             5046
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03298h2.cif
_cod_data_source_block           fsj20210716_0m
_cod_database_code               7130508
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.871
_shelx_estimated_absorpt_t_min   0.726
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9032(19)
 0.0968(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C19(H19), C15(H15)
3.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C32(H32), C33(H33), C25(H25), C34(H34), C13(H13), C2(H2), C31(H31),
 C30(H30), C12(H12), C5(H5), C23(H23), C3(H3), C24(H24), C6(H6), C4(H4),
 C11(H11), C14(H14)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'