Synthesis of 2-(1<i>H</i>-Indol-2-yl)acetamides via Brønsted Acid-Assisted Cyclization Cascade.
Aksenov, Nicolai A.; Aksenov, Dmitrii A.; Skomorokhov, Anton A.; Prityko, Lidiya A.; Aksenov, Alexander V.; Griaznov, Georgii D.; Rubin, Michael; The Journal of organic chemistry 85 (2020) 12128–12146; doi:10.1021/acs.joc.0c01344

data_4038787
_publ_section_title
;
 Synthesis of 2-(1<i>H</i>-Indol-2-yl)acetamides via Br\/onsted
 Acid-Assisted Cyclization Cascade.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12128
_journal_page_last               12146
_journal_paper_doi               10.1021/acs.joc.0c01344
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C16 H16 N2'
_chemical_formula_sum            'C16 H16 N2'
_chemical_formula_weight         236.31
_chemical_name_systematic        2-(1H-indol-2-yl)-2-phenylethan-1-amine
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.62377(13)
_cell_length_b                   11.62379(12)
_cell_length_c                   19.3359(2)
_cell_measurement_reflns_used    15499
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7520
_cell_measurement_theta_min      3.7710
_cell_volume                     2612.52(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -21.00  74.00   1.00    3.30    --   41.72 -77.00  60.00   95
  2  \w      8.00  42.00   1.00    3.30    --   41.72  81.00  94.22   34
  3  \w    -21.00  74.00   1.00    3.30    --   41.72 -77.00 -30.00   95
  4  \w     84.00 178.00   1.00   13.22    --  112.00  30.00   0.00   94
  5  \w     84.00 178.00   1.00   13.22    --  112.00  30.00  90.00   94
  6  \w    103.00 178.00   1.00   13.22    --  112.00  77.00 120.00   75
  7  \w     83.00 178.00   1.00   13.22    --  112.00  61.00 -30.00   95
  8  \w     36.00 109.00   1.00   13.22    --  112.00-111.00 -30.00   73
  9  \w     36.00 140.00   1.00   13.22    --  112.00 -30.00 120.00  104
 10  \w    104.00 178.00   1.00   13.22    --  112.00 111.00 120.00   74
 11  \w     36.00 109.00   1.00   13.22    --  112.00-111.00  60.00   73
 12  \w     30.00 106.00   1.00   13.22    --  112.00 -95.00 -30.00   76
 13  \w      8.00  42.00   1.00    3.30    --   41.72  81.00   4.57   34
 14  \w      8.00  42.00   1.00    3.30    --   41.72  82.00 -81.69   34
 15  \w      9.00  42.00   1.00    3.30    --   41.72  80.00-175.26   33
 16  \w     83.00 178.00   1.00   13.22    --  112.00  61.00-180.00   95
 17  \w     30.00 106.00   1.00   13.22    --  112.00 -95.00 150.00   76
 18  \w     39.00  64.00   1.00   13.22    --  112.00 -45.00  30.00   25
 19  \w     59.00 178.00   1.00   13.22    --  112.00  15.00 -90.00  119
 20  \w     41.00  66.00   1.00    3.30    --   41.60 -38.00 -30.00   25
 21  \w     41.00  67.00   1.00   13.22    --  112.00 -95.00 -90.00   26
 22  \w    146.00 172.00   1.00   13.22    --  112.00 111.00 -60.00   26
 23  \w   -116.00 -17.00   1.00    3.30    --  -41.60 -38.00  30.00   99
 24  \w   -116.00 -17.00   1.00    3.30    --  -41.60 -38.00 -60.00   99
 25  \w   -114.00 -13.00   1.00    3.30    --  -41.60 -57.00 150.00  101
 26  \w      6.00  35.00   1.00    3.30    --   41.60 -99.00-150.00   29
 27  \w   -116.00 -17.00   1.00    3.30    --  -41.60 -38.00-150.00   99
 28  \w   -115.00 -61.00   1.00    3.30    --  -41.60-150.00  37.00   54
 29  \w   -114.00 -13.00   1.00    3.30    --  -41.60 -57.00 120.00  101
 30  \w   -114.00 -13.00   1.00    3.30    --  -41.60 -57.00   0.00  101
 31  \w   -114.00 -89.00   1.00    3.30    --  -41.60 -57.00 -90.00   25
 32  \w      6.00  82.00   1.00    3.30    --   41.60 -99.00 -90.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1110486000
_diffrn_orient_matrix_UB_12      0.0308656000
_diffrn_orient_matrix_UB_13      0.0393413000
_diffrn_orient_matrix_UB_21      -0.0665015000
_diffrn_orient_matrix_UB_22      -0.0036064000
_diffrn_orient_matrix_UB_23      0.0688840000
_diffrn_orient_matrix_UB_31      0.0284596000
_diffrn_orient_matrix_UB_32      -0.1288370000
_diffrn_orient_matrix_UB_33      0.0074832000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0057
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31528
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.476
_diffrn_reflns_theta_min         4.574
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_preparation
'Compound was prepared by reduction of acetamide with LAH'
_exptl_crystal_recrystallization_method
'Crystal was prepared by evaporation of chloroform solution'
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0728P)^2^+0.3851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2444
_reflns_number_total             2722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01344_si_001.cif
_cod_data_source_block           anna1229_tryptamine_2
_cod_depositor_comments          'Adding full bibliography for 4038787.cif.'
_cod_database_code               4038787
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H16N2
_reflns_odcompleteness_completeness 98.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Others
 Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(N2)=1-FVAR(1)
 Sof(N3)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10A)=Sof(H10B)=FVAR(1)
 Sof(C19)=Sof(C24)=Sof(H24)=Sof(C23)=Sof(H23)=Sof(C22)=Sof(H22)=Sof(C21)=
 Sof(H21)=Sof(C20)=Sof(H20)=1-FVAR(2)
 Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=
 Sof(H15)=Sof(C16)=Sof(H16)=FVAR(2)
 Sof(H3A)=1-FVAR(3)
 Sof(H2A)=FVAR(3)
 Fixed Sof: H2B(0.1) H3B(0.9)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C2(H2), C7(H7), C4(H4),
 C5(H5), C6(H6), C24(H24), C23(H23), C22(H22), C21(H21), C20(H20)
3.d Fitted hexagon refined as free rotating group:
 C11(C12,C13,C14,C15,C16), C19(C24,C23,C22,C21,C20)
3.e X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_shelx_res_checksum              95681
_shelx_hkl_checksum              29129
_olex2_date_sample_data_collection 2020-08-05
_olex2_exptl_crystal_mounting_method
'Mounted by acrylic glue on the glass stick'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.714