Enantioselective intramolecular Pictet–Spengler type annulation of indole-linked 3-methyleneisoindolin-1-ones
Liu, Min; Li, Wenzhe; Huang, Min; Yan, Yingkun; Li, Min; Cao, Lianyi; Zhang, Xiaomei; New Journal of Chemistry 46 (2022) 9582–9586; doi:10.1039/D2NJ00517D

data_7061451
_publ_section_title
;
 Enantioselective intramolecular Pictet--Spengler type annulation of
 indole-linked 3-methyleneisoindolin-1-ones
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9582
_journal_page_last               9586
_journal_paper_doi               10.1039/D2NJ00517D
_journal_volume                  46
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H16 N2 O'
_chemical_formula_sum            'C19 H16 N2 O'
_chemical_formula_weight         288.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-09 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4363(4)
_cell_length_b                   14.1125(9)
_cell_length_c                   14.2240(9)
_cell_measurement_reflns_used    1796
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4240
_cell_measurement_theta_min      4.3910
_cell_volume                     1492.73(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_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    -64.00 -38.00   1.00    1.10    --  -33.50 -57.00  30.00   26
  2  \w    -71.00   2.00   1.00    1.10    --  -33.50  19.00 150.00   73
  3  \w    -14.00  21.00   1.00    1.10    --  -33.50  37.00-150.00   35
  4  \w     43.00  77.00   1.00    1.10    --   36.47 -99.00 -60.00   34
  5  \w     24.00  50.00   1.00    1.10    --   36.47 -57.00 -60.00   26
  6  \w    -31.00  -5.00   1.00    1.10    --   36.47 -57.00 -60.00   26
  7  \w    108.00 145.00   1.00    7.00    --  108.00 111.00  30.00   37
  8  \w    148.00 177.00   1.00    7.00    --  108.00  15.00-150.00   29
  9  \w     89.00 160.00   1.00    7.00    --  108.00  45.00   0.00   71
 10  \w     75.00 101.00   1.00    7.00    --  108.00  15.00-150.00   26
 11  \w    138.00 176.00   1.00    7.00    --  108.00 111.00 120.00   38
 12  \w    102.00 127.00   1.00    7.00    --  108.00 111.00 120.00   25
 13  \w     47.00 109.00   1.00    7.00    --  108.00 -94.00 -90.00   62
 14  \w    100.00 170.00   1.00    7.00    --  108.00 111.00-120.00   70
 15  \w    -57.00 -29.00   1.00    4.00    --  -33.50  77.00  60.00   28
 16  \w    -67.00 -41.00   1.00    4.00    --  -33.50 178.00   0.00   26
 17  \w    -93.00 -68.00   1.00    4.00    --  -33.50 -57.00-150.00   25
 18  \w     57.00  82.00   1.00    4.00    --   36.47 178.00-120.00   25
 19  \w     14.00  41.00   1.00    4.00    --   36.47 -37.00 -60.00   27
 20  \w     85.00 124.00   1.00    5.00    --  108.00 -30.00 -60.00   39
 21  \w     38.00  68.00   1.00    5.00    --  108.00 -30.00 -60.00   30
 22  \w     60.00  86.00   1.00    5.00    --  108.00 -94.00  60.00   26
 23  \w    108.00 135.00   1.00    5.00    --  108.00 111.00   0.00   27
 24  \w    111.00 177.00   1.00    5.00    --  108.00 111.00 150.00   66
 25  \w     11.00  36.00   1.00    4.00    --  -33.50  77.00-180.00   25
 26  \w     11.00  36.00   1.00    4.00    --  -33.50  77.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0284934000
_diffrn_orient_matrix_UB_12      0.1048715000
_diffrn_orient_matrix_UB_13      0.0261786000
_diffrn_orient_matrix_UB_21      0.0242195000
_diffrn_orient_matrix_UB_22      -0.0280847000
_diffrn_orient_matrix_UB_23      0.1038668000
_diffrn_orient_matrix_UB_31      0.2038412000
_diffrn_orient_matrix_UB_32      -0.0112127000
_diffrn_orient_matrix_UB_33      -0.0158923000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6222
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.085
_diffrn_reflns_theta_min         4.413
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 804 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0666P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1301
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                2346
_reflns_number_total             2815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj00517d2.cif
_cod_data_source_block           20200658
_cod_depositor_comments          'Adding full bibliography for 7061451.cif.'
_cod_original_cell_volume        1492.72(15)
_cod_database_code               7061451
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C14H15N2O4
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.905
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C2(H2A), C1(H1), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Fitted hexagon refined as free rotating group:
 C3(C2,C1,C6,C5,C4)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              41868
_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 1.094
_oxdiff_exptl_absorpt_empirical_full_min 0.911