Switchable regioselective hydroalkylation of 2-arylindoles with maleimides.
Nipate, Dhananjay S.; Shinde, Vikki N.; Rangan, Krishnan; Kumar, Anil; Organic & biomolecular chemistry 19 (2021) 4910–4921; doi:10.1039/d1ob00690h

data_7158053
_publ_section_title
;
 Switchable regioselective hydroalkylation of 2-arylindoles with
 maleimides.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4910
_journal_page_last               4921
_journal_paper_doi               10.1039/d1ob00690h
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34
_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     dual
_audit_creation_date             2020-10-16
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-03-07 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.086(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4146(6)
_cell_length_b                   9.1711(5)
_cell_length_c                   13.5882(8)
_cell_measurement_reflns_used    3818
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      78.5990
_cell_measurement_theta_min      4.3000
_cell_volume                     1493.77(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_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    -55.00  18.00   0.50    2.10    --    0.00 -37.00-150.00  146
  2  \w    -44.00 -16.00   0.50    2.10    --    0.00 -37.00 -60.00   56
  3  \w      0.00  25.00   0.50    2.10    --    0.00 -82.00-150.00   50
  4  \w    -88.00 -37.00   0.50    2.10    --    0.00 -82.00-150.00  102
  5  \w     33.00 139.00   0.50    8.41    --  107.20 -82.00-150.00  212
  6  \w     81.00 150.00   0.50    8.41    --  107.20  15.00  30.00  138
  7  \w     24.00 126.00   0.50    8.41    --  107.20 -30.00 -90.00  204
  8  \w    104.00 131.00   0.50    8.41    --  107.20 -82.00-120.00   54
  9  \w     89.00 130.00   0.50    8.41    --  107.20 -82.00 -90.00   82
 10  \w     21.00  94.00   0.50    8.41    --  107.20 -30.00-150.00  146
 11  \w     19.00 133.00   0.50    8.41    --  107.20 -15.00-180.00  228
 12  \w     95.00 128.00   0.50    8.41    --  107.20 -82.00 -60.00   66
 13  \w    105.00 139.00   0.50    8.41    --  107.20 -82.00 -30.00   68
 14  \w     81.00 138.00   0.50    8.41    --  107.20 -82.00-180.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0760447000
_diffrn_orient_matrix_UB_12      -0.0076413000
_diffrn_orient_matrix_UB_13      -0.1093024000
_diffrn_orient_matrix_UB_21      0.1035322000
_diffrn_orient_matrix_UB_22      0.0026456000
_diffrn_orient_matrix_UB_23      -0.0426410000
_diffrn_orient_matrix_UB_31      0.0050167000
_diffrn_orient_matrix_UB_32      -0.1677379000
_diffrn_orient_matrix_UB_33      0.0042412000
_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  0.0685
_diffrn_reflns_av_unetI/netI     0.0914
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8879
_diffrn_reflns_point_group_measured_fraction_full 0.710
_diffrn_reflns_point_group_measured_fraction_max 0.669
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.599
_diffrn_reflns_theta_min         3.369
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.129
_refine_ls_abs_structure_details
;
 Flack x determined using 801 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         4340
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0862
_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^)+(0.1658P)^2^+2.5438P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2693
_refine_ls_wR_factor_ref         0.2721
_reflns_Friedel_coverage         0.304
_reflns_Friedel_fraction_full    0.379
_reflns_Friedel_fraction_max     0.334
_reflns_number_gt                3898
_reflns_number_total             4340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00690h2.cif
_cod_data_source_block           exp_687-ak-dns-59
_cod_depositor_comments          'Adding full bibliography for 7158053.cif.'
_cod_database_code               7158053
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H16 N2 O2'
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.900
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 Ternary CH refined with riding coordinates:
 C15'(H15'), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16'(H16A,H16B), C16(H16C,H16D)
2.c Aromatic/amide H refined with riding coordinates:
 N1'(H1'), N1(H1), C11'(H11'), C13'(H13'), C12'(H12'), C5(H5), C7'(H7'),
 C2'(H2'), C4(H4), C3'(H3'), C4'(H4'), C7(H7), C14'(H14'), C3(H3), C5'(H5'),
 C14(H14), C11(H11), C2(H2), C13(H13), C12(H12)
2.d Idealised Me refined as rotating group:
 C19(H19D,H19E,H19F), C19'(H19A,H19B,H19C)
;
_shelx_res_checksum              56906
_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 3.474
_oxdiff_exptl_absorpt_empirical_full_min 0.551