Rh(iii)-Catalyzed C(sp2)‒H functionalization/cyclization cascade of N-carboxamide indole and iodonium reagents for access to indoloquinazolinone derivatives
Han, Zhi-Peng; Xu, Meng-Meng; Zhang, Rui-Ying; Xu, Xiao-Ping; Ji, Shun-Jun; Green Chemistry 23 (2021) 6337–6340; doi:10.1039/D1GC01820E

data_7243303
_publ_section_title
;
 Rh(iii)-Catalyzed C(sp2)--H functionalization/cyclization cascade of
 N-carboxamide indole and iodonium reagents for access to
 indoloquinazolinone derivatives
;
_journal_issue                   17
_journal_name_full               'Green Chemistry'
_journal_page_first              6337
_journal_page_last               6340
_journal_paper_doi               10.1039/D1GC01820E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C18 H18 N2 O3'
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.34
_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             2021-01-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-03-17 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                110.924(12)
_cell_angle_beta                 95.681(9)
_cell_angle_gamma                108.558(12)
_cell_formula_units_Z            2
_cell_length_a                   8.4879(10)
_cell_length_b                   9.8238(14)
_cell_length_c                   10.6092(11)
_cell_measurement_reflns_used    1282
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0660
_cell_measurement_theta_min      4.5930
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega  -10.00   27.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843   37.0000  150.0000 37

  2 omega -127.00 -101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843    0.0000  -90.0000 26

  3 omega  -46.00  -15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843   37.0000  150.0000 31

  4 omega  -75.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843    0.0000  -90.0000 122

  5 omega   35.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9843  -99.0000  120.0000 37

  6 omega   22.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9843 -125.0000  -90.0000 55

  7 omega   36.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9843 -131.0000   98.0000 29

  8 omega   -2.00   71.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9843  -99.0000  -30.0000 73

  9 omega  133.00  159.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000   90.0000 26

 10 omega   37.00   71.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   30.0000 34

 11 omega   36.00  111.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  -30.0000 75

 12 omega  114.00  164.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  -90.0000 50

 13 omega  139.00  165.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000 -180.0000 26

 14 omega   77.00  115.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000   30.0000 38

 15 omega   54.00   80.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -82.0000  134.5010 26

 16 omega   99.00  149.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  178.0000    0.0000 50

 17 omega   69.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -138.0000  -77.0000 26

 18 omega   88.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  150.0000 28

 19 omega   60.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   60.0000 31

 20 omega   97.00  143.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000  -60.0000 46

 21 omega   37.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  150.0000 45

 22 omega   36.00  101.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000   60.0000 65

 23 omega   51.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000  150.0000 33

 24 omega  124.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  150.0000 53

 25 omega   37.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  120.0000 51

 26 omega   61.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  178.0000  120.0000 32

 27 omega   55.00  144.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000  150.0000 89

 28 omega  114.00  147.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  178.0000 -150.0000 33

 29 omega   40.00   66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000  -90.0000 26

 30 omega   84.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000  -90.0000 25

 31 omega   98.00  145.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  178.0000   90.0000 47

 32 omega   68.00   94.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  178.0000   90.0000 26

 33 omega  128.00  169.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  120.0000 41

 34 omega   61.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  -90.0000 25

 35 omega   93.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000 -120.0000 84

 36 omega   72.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000    0.0000 25

 37 omega   37.00   63.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000   90.0000 26

 38 omega   73.00  112.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000   90.0000 39

 39 omega   84.00  112.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -82.0000  134.5010 28

 40 omega  140.00  166.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000   30.0000 26

 41 omega   83.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -82.0000   56.7392 25

 42 omega   40.00   66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -82.0000   56.7392 26
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0149891000
_diffrn_orient_matrix_UB_12      0.0652797000
_diffrn_orient_matrix_UB_13      -0.1109131000
_diffrn_orient_matrix_UB_21      0.0550940000
_diffrn_orient_matrix_UB_22      0.1669647000
_diffrn_orient_matrix_UB_23      0.1155009000
_diffrn_orient_matrix_UB_31      0.1887818000
_diffrn_orient_matrix_UB_32      0.0286135000
_diffrn_orient_matrix_UB_33      -0.0023338000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7565
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.386
_diffrn_reflns_theta_min         4.597
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0840
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1557P)^2^+0.0545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2306
_refine_ls_wR_factor_ref         0.3080
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1846
_reflns_number_total             3191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc01820e2.cif
_cod_data_source_block           g210105a
_cod_depositor_comments          'Adding full bibliography for 7243303.cif.'
_cod_original_cell_volume        760.40(18)
_cod_database_code               7243303
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C N O H'
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.833
_reflns_odcompleteness_completeness 95.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B), C00G(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00H(H00H), C00J(H00J), C00L(H00N), C00M(H00O)
2.c Idealised Me refined as rotating group:
 C00I(H00F,H00G,H00I), C00K(H00K,H00L,H00M), C00N(H00P,H00Q,H00R)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              85634
_olex2_submission_special_instructions 'No special instructions were received'