Synthesis of indolines via a palladium/norbornene-catalyzed reaction of aziridines with aryl iodides.
Liu, Ce; Liang, Yujie; Zheng, Nian; Zhang, Bo-Sheng; Feng, Yuan; Bi, Siwei; Liang, Yong-Min; Chemical communications (Cambridge, England) 54 (2018) 3407–3410; doi:10.1039/C8CC01062E

data_7121385
_publ_section_title
;
 Synthesis of indolines via a palladium/norbornene-catalyzed reaction of
 aziridines with aryl iodides.
;
_journal_issue                   27
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3407
_journal_page_last               3410
_journal_paper_doi               10.1039/C8CC01062E
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H18 Br N O2 S'
_chemical_formula_sum            'C24 H18 Br N O2 S'
_chemical_formula_weight         464.36
_chemical_name_systematic
(R)-1-((4-bromophenyl)sulfonyl)-2-phenyl-2,3-dihydro-1H-benzo[g]indole
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-01-09 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.605(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.2737(10)
_cell_length_b                   8.0033(8)
_cell_length_c                   11.9357(10)
_cell_measurement_reflns_used    807
_cell_measurement_temperature    289.50(10)
_cell_measurement_theta_max      24.9940
_cell_measurement_theta_min      3.8060
_cell_volume                     1020.64(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      289.50(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -97.00  -58.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000   90.0000 26

  2 omega    8.00   66.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000  -90.0000 39

  3 omega  -34.00   86.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000   90.0000 80
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0535642000
_diffrn_orient_matrix_UB_12      -0.0521785000
_diffrn_orient_matrix_UB_13      0.0139267000
_diffrn_orient_matrix_UB_21      -0.0387964000
_diffrn_orient_matrix_UB_22      -0.0716321000
_diffrn_orient_matrix_UB_23      -0.0069876000
_diffrn_orient_matrix_UB_31      -0.0052445000
_diffrn_orient_matrix_UB_32      -0.0038427000
_diffrn_orient_matrix_UB_33      -0.0607621000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3728
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.34
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0305P)^2^+0.0412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                1913
_reflns_number_total             2564
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc01062e2.cif
_cod_data_source_block           liuc_547_2
_cod_depositor_comments
'Adding full bibliography for 7121384--7121390.cif.'
_cod_original_cell_volume        1020.64(16)
_cod_database_code               7121385
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
;
_olex2_date_sample_data_collection 2017-05-03
_olex2_submission_special_instructions 'No special instructions were received'