Accessing pyrrolo[1,2-<i>a</i>]indole derivatives <i>via</i> visible-light-induced dearomatizative cyclization of indoles.
Liu, Zhaosheng; Ji, Xiaochen; Duan, Lilan; Deng, Guo-Jun; Huang, Huawen; Chemical communications (Cambridge, England) 60 (2024) 4902–4905; doi:10.1039/d4cc01215a

data_7132952
_publ_section_title
;
 Accessing pyrrolo[1,2-<i>a</i>]indole derivatives <i>via</i>
 visible-light-induced dearomatizative cyclization of indoles.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4902
_journal_page_last               4905
_journal_paper_doi               10.1039/d4cc01215a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C16 H19 N O2'
_chemical_formula_sum            'C16 H19 N O2'
_chemical_formula_weight         257.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-04-25
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-03-09 deposited with the CCDC.	2024-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.147(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   16.3685(3)
_cell_length_b                   10.1416(2)
_cell_length_c                   33.0222(7)
_cell_measurement_reflns_used    12032
_cell_measurement_temperature    295.62(13)
_cell_measurement_theta_max      76.3260
_cell_measurement_theta_min      2.6750
_cell_volume                     5477.93(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.62(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -118.00 -73.00   0.50    0.80    --  -47.70-125.00 170.00   90
  2  \w    -85.00 -40.00   0.50    0.80    --  -47.70 125.00-111.00   90
  3  \w   -119.00 -76.00   0.50    0.80    --  -47.70-146.00   3.00   86
  4  \w     54.00  94.00   0.50    0.80    --   47.70-125.00 170.00   80
  5  \w     53.00  78.00   0.50    0.80    --   47.70-146.00   3.00   50
  6  \w   -131.00 -86.00   0.50    2.50    --  -86.25-125.00 170.00   90
  7  \w     81.00 127.00   0.50    2.50    --  107.75-146.00   3.00   92
  8  \w     95.00 160.00   0.50    2.50    --  107.75 125.00-111.00  130
  9  \w    117.00 143.00   0.50    2.50    --  107.75 146.00  55.00   52
 10  \w     86.00 112.00   0.50    2.50    --  107.75-125.00 170.00   52
 11  \w    -89.00 -33.00   0.50    0.80    --  -47.70 -57.00  90.00  112
 12  \w   -118.00 -78.00   0.50    0.80    --  -47.70-125.00 -60.00   80
 13  \w    -27.00  28.00   0.50    0.80    --  -47.70  19.00  30.00  110
 14  \w   -118.00 -93.00   0.50    0.80    --  -47.70 -57.00  90.00   50
 15  \w     -6.00  20.00   0.50    0.80    --   47.70 -19.00 -30.00   52
 16  \w    -41.00 -15.00   0.50    2.50    --  -86.25  37.00 120.00   52
 17  \w    -40.00 -15.00   0.50    2.50    --  -86.25  37.00  60.00   50
 18  \w    -66.00 -30.00   0.50    2.50    --  -86.25  57.00  30.00   72
 19  \w     35.00 104.00   0.50    2.50    --  107.75 -99.00-180.00  138
 20  \w     35.00  61.00   0.50    2.50    --  107.75 -57.00-150.00   52
 21  \w     36.00  62.00   0.50    2.50    --  107.75 -57.00-180.00   52
 22  \w     49.00  92.00   0.50    2.50    --  107.75 -99.00  60.00   86
 23  \w     35.00 103.00   0.50    2.50    --  107.75 -99.00 -30.00  136
 24  \w     36.00  66.00   0.50    2.50    --  107.75 -57.00 120.00   60
 25  \w     66.00  96.00   0.50    2.50    --  107.75 -99.00-150.00   60
 26  \w    113.00 167.00   0.50    2.50    --  107.75  19.00   0.00  108
 27  \w     95.00 178.00   0.50    2.50    --  107.75  37.00  60.00  166
 28  \w     76.00 108.00   0.50    2.50    --  107.75-109.00 126.86   64
 29  \w     36.00  65.00   0.50    2.50    --  107.75 -57.00   0.00   58
 30  \w     35.00  64.00   0.50    2.50    --  107.75 -57.00 -60.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0155356000
_diffrn_orient_matrix_UB_12      0.1314029000
_diffrn_orient_matrix_UB_13      0.0218253000
_diffrn_orient_matrix_UB_21      0.0409102000
_diffrn_orient_matrix_UB_22      0.0752184000
_diffrn_orient_matrix_UB_23      -0.0343555000
_diffrn_orient_matrix_UB_31      -0.0833838000
_diffrn_orient_matrix_UB_32      0.0123911000
_diffrn_orient_matrix_UB_33      -0.0228701000
_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  0.0723
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            39310
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         2.678
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     693
_refine_ls_number_reflns         9638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0728
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2019
_refine_ls_wR_factor_ref         0.2424
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6577
_reflns_number_total             9638
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01215a2.cif
_cod_data_source_block           2942
_cod_depositor_comments
'Adding full bibliography for 7132952--7132953.cif.'
_cod_database_code               7132952
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.914
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C68(H68), C49(H49), C14(H14), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C15(H15A,H15B), C24(H24A,H24B), C5(H5A,H5B), C27(H27A,H27B),
 C43(H43A,H43B), C62(H62A,H62B), C67(H67A,H67B), C2(H2A,H2B), C65(H65A,H65B),
 C46(H46A,H46B), C48(H48A,H48B), C4(H4A,H4B), C3(H3A,H3B), C26(H26A,H26B),
 C25(H25A,H25B), C44(H44A,H44B), C63(H63A,H63B), C64(H64A,H64B), C45(H45A,H45B)
2.c Aromatic/amide H refined with riding coordinates:
 C73(H73), C54(H54), C51(H51), C52(H52), C70(H70), C11(H11), C72(H72),
 C53(H53), C35(H35), C32(H32), C8(H8), C71(H71), C33(H33), C10(H10), C34(H34),
 C9(H9)
2.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C16(H16A,H16B,H16C), C76(H76A,H76B,H76C), C57(H57A,H57B,
 H57C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O36(H36), O55(H55), O74(H74)
;
_shelx_res_checksum              94494
_shelx_hkl_checksum              93842
_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 2.024
_oxdiff_exptl_absorpt_empirical_full_min 0.395