Palladium Tandem Catalysis in the Atropodiastereoselective Synthesis of Indenes Bearing Central and Axial Chirality
Borie, Cyril; Vanthuyne, Nicolas; Bertrand, Michèle P.; Siri, Didier; Nechab, Malek; ACS Catalysis 6 (2016) 1559–; doi:10.1021/acscatal.5b02867

data_4513807
_publ_section_title
;
 Palladium Tandem Catalysis in the Atropodiastereoselective Synthesis of
 Indenes Bearing Central and Axial Chirality
;
_journal_issue                   3
_journal_name_full               'ACS Catalysis'
_journal_page_first              1559
_journal_paper_doi               10.1021/acscatal.5b02867
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C26 H21 N'
_chemical_formula_sum            'C26 H21 N'
_chemical_formula_weight         347.44
_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
_audit_creation_date             2015-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                86.213(4)
_cell_angle_beta                 78.340(4)
_cell_angle_gamma                86.602(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2190(4)
_cell_length_b                   10.1031(6)
_cell_length_c                   12.1768(6)
_cell_measurement_reflns_used    3147
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.7850
_cell_measurement_theta_min      3.6850
_cell_volume                     987.01(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega  -77.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014   77.0000  150.0000 137

  2 omega  -62.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014  125.0000  -90.0000 38

  3 omega  -85.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014  125.0000 -180.0000 70

  4 omega   75.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667   38.0000 -180.0000 93

  5 omega  109.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667   77.0000 -150.0000 67

  6 omega  121.00  147.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  178.0000 -180.0000 26

  7 omega   67.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667   77.0000 -150.0000 26

  8 omega   64.00  173.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667   38.0000  -90.0000 109

  9 omega   68.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667 -111.0000 -120.0000 47

 10 omega   31.00  146.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  -63.0000 -180.0000 115

 11 omega   32.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  -25.0000 -120.0000 37

 12 omega   33.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.6014 -125.0000   60.0000 47

 13 omega   47.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  -50.0000   60.0000 42

 14 omega   23.00  151.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  -91.0000   60.0000 128

 15 omega  121.00  167.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  111.0000  150.0000 46

 16 omega   60.00  150.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  178.0000   90.0000 90

 17 omega   59.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  178.0000   60.0000 49

 18 omega -112.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014  -99.0000  -90.0000 33

 19 omega -124.00  -81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014  -99.0000  -30.0000 43

 20 omega -120.00  -87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014  -99.0000 -180.0000 33

 21 omega -122.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014 -125.0000  -90.0000 34

 22 omega -125.00  -83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014  -99.0000  120.0000 42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0517321000
_diffrn_orient_matrix_UB_12      0.1155918000
_diffrn_orient_matrix_UB_13      0.0598981000
_diffrn_orient_matrix_UB_21      0.1570611000
_diffrn_orient_matrix_UB_22      0.0142783000
_diffrn_orient_matrix_UB_23      -0.0927180000
_diffrn_orient_matrix_UB_31      -0.0967788000
_diffrn_orient_matrix_UB_32      0.0991956000
_diffrn_orient_matrix_UB_33      -0.0674893000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5882
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.657
_diffrn_reflns_theta_min         3.712
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.511
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.169
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0524P)^2^+0.1326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3094
_reflns_number_total             3576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs5b02867_si_003.cif
_cod_data_source_block           mn7124f1
_cod_depositor_comments          'Adding full bibliography for 4513807.cif.'
_cod_database_code               4513807
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C23(H23), C24(H24)
2.d X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'