Desymmetrization of cyclohexa-2,5-dienes through a diastereoselective protonation-hydroamination cascade.
Lebeuf, Raphaël; Robert, Frédéric; Schenk, Kurt; Landais, Yannick; Organic letters 8 (2006) 4755–4758; doi:10.1021/ol0618353

data_1506209
_publ_section_title
;
 Desymmetrization of cyclohexa-2,5-dienes through a diastereoselective
 protonation-hydroamination cascade.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4755
_journal_page_last               4758
_journal_paper_doi               10.1021/ol0618353
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration unkn
_chemical_formula_moiety         'C25 H31 N O3'
_chemical_formula_sum            'C25 H31 N O3'
_chemical_formula_weight         393.51
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             05-12-09
_audit_creation_method           'SHELXL-97 and STOE X-RED'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.447(2)
_cell_length_b                   11.215(2)
_cell_length_c                   37.269(8)
_cell_measurement_reflns_used    26281
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.50
_cell_measurement_theta_min      1.82
_cell_volume                     4366.6(15)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Bruker SHELXTL, (Bruker, 1996)'
_computing_publication_material  'Bruker SHELXTL, PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL-96 (Sheldrick, 1996)'
_computing_structure_solution    'SIR97 (Moliterni, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      ' 180 frames, detector distance = 100 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       rotation
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            42463
_diffrn_reflns_theta_full        29.26
_diffrn_reflns_theta_max         29.26
_diffrn_reflns_theta_min         1.90
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           45
_diffrn_source_power             2.48
_diffrn_source_voltage           55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_correction_T_min  0.9639
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Stoe X-Red 1.22'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.494
_exptl_crystal_size_mid          0.332
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0075(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   2.765
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         6560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.765
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0618
_reflns_number_gt                4898
_reflns_number_total             6560
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0618353si20060725_100250.cif
_cod_data_source_block           17
_cod_original_cell_volume        4366.4(15)
_cod_database_code               1506209
_audit_contact_author            'Kurt Schenk'