Palladium-catalyzed dearomative cyclization by a norbornene-mediated sequence: a route to spiroindolenine derivatives
Xin-Xing Wu; Yi Shen; Wen-Long Chen; Si Chen; Peng-Fei Xu; Yong-Min Liang; Chem.Commun. 51 (2015) 16798–; doi:10.1039/C5cc07411H

data_7118087
_publ_section_title
;
 Palladium-catalyzed dearomative cyclization by a norbornene-mediated
 sequence: a route to spiroindolenine derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              16798
_journal_paper_doi               10.1039/C5cc07411H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C22 H25 N'
_chemical_formula_sum            'C22 H25 N'
_chemical_formula_weight         303.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-17
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-20 deposited with the CCDC.
2015-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.3630(6)
_cell_length_b                   16.4293(8)
_cell_length_c                   25.6720(15)
_cell_measurement_reflns_used    1860
_cell_measurement_temperature    294.76(10)
_cell_measurement_theta_max      68.5740
_cell_measurement_theta_min      8.2870
_cell_volume                     3527.3(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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.76(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega   64.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 26

  2 omega   49.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 29

  3 omega   38.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 57

  4 omega   36.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 28

  5 omega   24.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -90.0000 59

  6 omega   15.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 53

  7 omega   75.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 43

  8 omega  106.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 70

  9 omega  113.00  139.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 26

 10 omega  100.00  161.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 61

 11 omega   58.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 26

 12 omega   37.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 72

 13 omega    9.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 52
;
_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      0.0393957000
_diffrn_orient_matrix_UB_12      -0.0029597000
_diffrn_orient_matrix_UB_13      -0.0586418000
_diffrn_orient_matrix_UB_21      -0.1576873000
_diffrn_orient_matrix_UB_22      -0.0456815000
_diffrn_orient_matrix_UB_23      -0.0102716000
_diffrn_orient_matrix_UB_31      -0.0865140000
_diffrn_orient_matrix_UB_32      0.0818230000
_diffrn_orient_matrix_UB_33      -0.0078103000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7857
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.165
_diffrn_reflns_theta_min         3.443
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79864
_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    1.143
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0630
_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^)+(0.1093P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.2038
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2168
_reflns_number_total             3289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc07411h2.cif
_cod_data_source_block           wuxx_35_3
_cod_database_code               7118087
_reflns_odcompleteness_completeness 99.53
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C15(H15), C8(H8), C14(H14), C3(H3), C2(H2), C13(H13)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C21(H21A,H21B,
 H21C)
;
_shelx_res_checksum              65635
_shelx_hkl_checksum              89344
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'