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_1572103
_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_formula_moiety         'C33 H32 N2 O2 S'
_chemical_formula_sum            'C33 H32 N2 O2 S'
_chemical_formula_weight         520.67
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-11-01
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.115(3)
_cell_length_b                   20.818(4)
_cell_length_c                   21.153(3)
_cell_measurement_reflns_used    922
_cell_measurement_temperature    115.00(14)
_cell_measurement_theta_max      20.0690
_cell_measurement_theta_min      3.4730
_cell_volume                     5335.0(18)
_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      115.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.8622
_diffrn_measurement_details
;
  1 omega   54.00   82.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   57.0000   30.0000 28

  2 omega   39.00   85.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  178.0000  150.0000 46

  3 omega  -34.00   57.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508   77.0000 -120.0000 91

  4 omega  -53.00  -18.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -37.0000  -30.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0295596000
_diffrn_orient_matrix_UB_12      0.0294141000
_diffrn_orient_matrix_UB_13      0.0009192000
_diffrn_orient_matrix_UB_21      0.0279573000
_diffrn_orient_matrix_UB_22      0.0104562000
_diffrn_orient_matrix_UB_23      -0.0276767000
_diffrn_orient_matrix_UB_31      -0.0420205000
_diffrn_orient_matrix_UB_32      -0.0137612000
_diffrn_orient_matrix_UB_33      -0.0189745000
_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  0.1344
_diffrn_reflns_av_unetI/netI     0.1528
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20010
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.22
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87068
_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    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1700
_refine_ls_R_factor_gt           0.0783
_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^)+(0.0319P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1670
_reflns_number_gt                2591
_reflns_number_total             5213
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4sc02802c2.cif
_cod_data_source_block           exp_8244
_cod_depositor_comments
'Adding full bibliography for 1572101--1572103.cif.'
_cod_original_cell_volume        5334.8(19)
_cod_database_code               1572103
_chemical_oxdiff_formula         C2
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07