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_7121387
_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_formula_moiety         'C28 H25 N3 O2 Pd S'
_chemical_formula_sum            'C28 H25 N3 O2 Pd S'
_chemical_formula_weight         573.97
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-03-09
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2018-01-09 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                87.411(13)
_cell_angle_beta                 88.915(16)
_cell_angle_gamma                80.386(13)
_cell_formula_units_Z            2
_cell_length_a                   8.1719(16)
_cell_length_b                   9.5500(11)
_cell_length_c                   15.502(3)
_cell_measurement_reflns_used    1289
_cell_measurement_temperature    291.17(10)
_cell_measurement_theta_max      23.1390
_cell_measurement_theta_min      3.7960
_cell_volume                     1191.5(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.17(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -13.00   19.00   2.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  150.0000 16

  2 omega  -35.00   89.00   2.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000   30.0000 62

  3 omega   -1.00   93.00   2.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000    0.0000 47

  4 omega   74.00  102.00   2.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -150.0000 14

  5 omega  -45.00   47.00   2.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -150.0000 46

  6 omega  -12.00   16.00   2.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000    0.0000 14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0570614000
_diffrn_orient_matrix_UB_12      0.0181353000
_diffrn_orient_matrix_UB_13      -0.0342313000
_diffrn_orient_matrix_UB_21      -0.0670194000
_diffrn_orient_matrix_UB_22      0.0030052000
_diffrn_orient_matrix_UB_23      0.0299805000
_diffrn_orient_matrix_UB_31      0.0018054000
_diffrn_orient_matrix_UB_32      0.0731232000
_diffrn_orient_matrix_UB_33      0.0052438000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.1214
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7926
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         3.336
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.600
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.045
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0191P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3328
_reflns_number_total             4671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc01062e2.cif
_cod_data_source_block           liuc_0308_2
_cod_depositor_comments
'Adding full bibliography for 7121384--7121390.cif.'
_cod_database_code               7121387
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O Pd S'
_reflns_odcompleteness_completeness 99.75
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_olex2_date_sample_data_collection 2017-03-08
_olex2_submission_special_instructions 'No special instructions were received'