Accessing indole-isoindole derivatives via palladium-catalyzed [3+2] cyclization of isocyanides with alkynyl imines
Chen, Dianpeng; Li, Jianming; Liu, Gongle; Zhang, Xiuhua; Wang, Xin; Liu, Yongwei; Liu, Xuan; Liu, Xinghai; Li, Yongqin; Shan, Yingying; Chemical Communications  (2023) –; doi:10.1039/D3CC02654J

data_7131945
_publ_section_title
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 Accessing indole-isoindole derivatives via palladium-catalyzed [3+2]
 cyclization of isocyanides with alkynyl imines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02654J
_journal_year                    2023
_chemical_formula_moiety         'C27 H23 N3'
_chemical_formula_sum            'C27 H23 N3'
_chemical_formula_weight         389.48
_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_block_doi                 10.5517/ccdc.csd.cc2g0cpk
_audit_creation_date             2020-12-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2023-05-22 deposited with the CCDC.	2023-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                74.345(2)
_cell_angle_beta                 81.891(2)
_cell_angle_gamma                89.567(2)
_cell_formula_units_Z            4
_cell_length_a                   10.9750(7)
_cell_length_b                   12.9016(8)
_cell_length_c                   15.8408(11)
_cell_measurement_reflns_used    9729
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.584
_cell_measurement_theta_min      2.509
_cell_volume                     2137.1(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0670
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            59928
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.587
_diffrn_reflns_theta_min         2.146
_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  0.7456
_exptl_absorpt_correction_T_min  0.5976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1390 before and 0.0819 after correction.
The Ratio of minimum to maximum transmission is 0.8015.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     587
_refine_ls_number_reflns         9892
_refine_ls_number_restraints     1072
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0413P)^2^+0.8996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8531
_reflns_number_total             9892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02654j2.cif
_cod_data_source_block           a
_cod_database_code               7131945
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.972
_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. Restrained distances
 C54-C35 = C52-C35 = C53-C35
 1.51 with sigma of 0.02
 C52A-C35A = C54A-C35A = C53A-C35A
 1.51 with sigma of 0.02
 N1-C35A
 1.45 with sigma of 0.02
 N1-C9 = N1-C13 = N1-C35
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(C52A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C35A)=Sof(C52A)=Sof(H52D)=Sof(H52E)=Sof(H52F)=Sof(C54A)=Sof(H54D)=
 Sof(H54E)=Sof(H54F)=Sof(C53A)=Sof(H53D)=Sof(H53E)=Sof(H53F)=1-FVAR(1)
 Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=
 Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=Sof(C35)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C7(H7), C18(H18), C21(H21), C22(H22), C23(H23), C25(H25),
 C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C33(H33), C34(H34), C36(H36),
  C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C43(H43), C45(H45),
 C46(H46), C47(H47), C49(H49), C50(H50), C51(H51)
6.b Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C44(H44A,H44B,H44C), C48(H48A,H48B,H48C), C52(H52A,H52B,
 H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C), C52A(H52D,H52E,H52F),
 C54A(H54D,H54E,H54F), C53A(H53D,H53E,H53F)
;
_shelx_res_checksum              40596
_shelx_hkl_checksum              25098
_olex2_submission_special_instructions 'No special instructions were received'