C-H functionalization of 2-alkyl tryptamines: direct assembly of azepino[4,5-<i>b</i>]indoles and total synthesis of ngouniensines.
Xie, Kejing; Shen, Zeyuan; Cheng, Peng; Dong, Haoxiang; Yu, Zhi-Xiang; Zu, Liansuo; Chemical science 15 (2024) 12732–12738; doi:10.1039/d4sc02802c

data_1572101
_publ_section_title
;
 C-H functionalization of 2-alkyl tryptamines: direct assembly of
 azepino[4,5-<i>b</i>]indoles and total synthesis of ngouniensines.
;
_journal_issue                   32
_journal_name_full               'Chemical science'
_journal_page_first              12732
_journal_page_last               12738
_journal_paper_doi               10.1039/d4sc02802c
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H22 N2'
_chemical_formula_sum            'C20 H22 N2'
_chemical_formula_weight         290.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-03-24
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2023-07-26 deposited with the CCDC.	2024-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.67(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8833(11)
_cell_length_b                   7.8177(10)
_cell_length_c                   14.677(4)
_cell_measurement_reflns_used    1632
_cell_measurement_temperature    111.60(14)
_cell_measurement_theta_max      24.9360
_cell_measurement_theta_min      3.7500
_cell_volume                     778.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      111.60(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.8720
_diffrn_measurement_details
;
  1 omega   32.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   37.0000   90.0000 53

  2 omega    1.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   77.0000  -30.0000 82

  3 omega  -24.00    4.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000 -150.0000 28

  4 omega   32.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289 -178.0000 -120.0000 49

  5 omega  -47.00  -11.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.7727  -37.0000   90.0000 36

  6 omega   17.00   52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -99.0000 -150.0000 35

  7 omega  -33.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -19.0000    0.0000 71

  8 omega   39.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  178.0000   60.0000 47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0551334000
_diffrn_orient_matrix_UB_12      -0.0275876000
_diffrn_orient_matrix_UB_13      0.0426956000
_diffrn_orient_matrix_UB_21      0.0506052000
_diffrn_orient_matrix_UB_22      -0.0597882000
_diffrn_orient_matrix_UB_23      -0.0237741000
_diffrn_orient_matrix_UB_31      0.0729822000
_diffrn_orient_matrix_UB_32      0.0624867000
_diffrn_orient_matrix_UB_33      -0.0039350000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6324
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+0.1525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1337
_reflns_number_gt                2434
_reflns_number_total             2965
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4sc02802c2.cif
_cod_data_source_block           exp_7889
_cod_depositor_comments
'Adding full bibliography for 1572101--1572103.cif.'
_cod_database_code               1572101
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07