A one-pot, three-step process for the diastereoselective synthesis of aminobicyclo[4.3.0]nonanes using consecutive palladium(ii)- and ruthenium(ii)-catalysis.
Mostafa, Mohamed A. B.; Grafton, Mark W.; Wilson, Claire; Sutherland, Andrew; Organic & biomolecular chemistry 14 (2016) 3284–3297; doi:10.1039/c6ob00165c

data_7154994
_publ_section_title
;
 A one-pot, three-step process for the diastereoselective synthesis of
 aminobicyclo[4.3.0]nonanes using consecutive palladium(ii)- and
 ruthenium(ii)-catalysis.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3284
_journal_page_last               3297
_journal_paper_doi               10.1039/c6ob00165c
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C25 H23 Cl3 N2 O5, C H4 O'
_chemical_formula_sum            'C26 H27 Cl3 N2 O6'
_chemical_formula_weight         569.84
_chemical_name_systematic
(3aS*,5R*,5aR*,8R*,8aR*,8bR*)-5,5a-dihydroxy-2,5-diphenyl-3a,4,5,5a,6,7,8a,8b-octahydro-8-(2',2',2'-trichloromethylcarbonylamino)cyclopent[e]isoindole-1,3(2H,3aH)-dione
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date
;
'Wed Sep 09 11:56:03 2015'
;
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_audit_update_record
;
2015-10-05 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.096(3)
_cell_angle_beta                 95.408(3)
_cell_angle_gamma                91.971(3)
_cell_formula_units_Z            4
_cell_length_a                   11.7084(4)
_cell_length_b                   14.1127(6)
_cell_length_c                   15.5928(6)
_cell_measurement_reflns_used    11249
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4920
_cell_measurement_theta_min      2.5080
_cell_volume                     2563.49(17)
_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
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_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, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -27.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000   72.0000  120.0000 100

  2 omega  -77.00   22.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000  -72.0000    0.0000 99

  3 omega  -68.00   22.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000  -72.0000 -180.0000 90

  4 omega  -87.00  -21.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000    0.0000    0.0000 66

  5 omega  -31.00  -13.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000   54.0000  -30.0000 18

  6 omega  -35.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000   72.0000  150.0000 108

  7 omega  -69.00   11.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0000  -72.0000   30.0000 80
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0408486000
_diffrn_orient_matrix_UB_12      0.0113760000
_diffrn_orient_matrix_UB_13      -0.0295363000
_diffrn_orient_matrix_UB_21      0.0451434000
_diffrn_orient_matrix_UB_22      -0.0069645000
_diffrn_orient_matrix_UB_23      0.0327798000
_diffrn_orient_matrix_UB_31      0.0009077000
_diffrn_orient_matrix_UB_32      -0.0484890000
_diffrn_orient_matrix_UB_33      -0.0118715000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34139
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.229
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46404
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       blade
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.2590
_exptl_crystal_size_mid          0.0470
_exptl_crystal_size_min          0.0150
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     675
_refine_ls_number_reflns         9008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0700P)^2^+0.5780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1355
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6437
_reflns_number_total             9008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00165c2.cif
_cod_data_source_block           2015ncs0547
_cod_depositor_comments          'Adding full bibliography for 7154994.cif.'
_cod_original_cell_volume        2563.48(17)
_cod_database_code               7154994
_chemical_oxdiff_formula         C25H23Cl3N2O5
_cell_oxdiff_angle_alpha         90.096(3)
_cell_oxdiff_angle_beta          95.408(3)
_cell_oxdiff_angle_gamma         91.971(3)
_cell_oxdiff_length_a            11.7084(4)
_cell_oxdiff_length_b            14.1127(6)
_cell_oxdiff_length_c            15.5928(6)
_cell_oxdiff_measurement_reflns_used 11249
_cell_oxdiff_volume              2563.48(17)
_reflns_odcompleteness_completeness 99.94
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C3A(H3A), C8A(H8A), C8B(H8B), C28(H28), C23A(H23A), C28A(H28A),
 C28B(H28B)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C24(H24A,H24B), C26(H26A,H26B),
 C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C102(H102), C103(H103), C104(H104), C105(H105), C106(H106),
 C112(H112), C113(H113), C114(H114), C115(H115), C116(H116), N21(H21),
 C202(H202), C203(H203), C204(H204), C205(H205), C206(H206), C212(H212),
 C213(H213), C214(H214), C215(H215), C216(H216)
2.d Idealised Me refined as rotating group:
 C1M(H1MA,H1MB,H1MC), C2M(H2MA,H2MB,H2MC)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O5A(H5A), O25(H25), O25A(H25A), O1M(H1M), O2M(H2M)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'