Rhodium-catalyzed enantio- and diastereoselective intramolecular [2 + 2 + 2] cycloaddition of unsymmetrical dienynes.
Sagae, Hiromi; Noguchi, Keiichi; Hirano, Masao; Tanaka, Ken; Chemical communications (Cambridge, England)  (2008) 3804–3806; doi:10.1039/b804294b

data_7103288
_publ_section_title
;
 Rhodium-catalyzed enantio- and diastereoselective intramolecular [2 +
 2 + 2] cycloaddition of unsymmetrical dienynes.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3804
_journal_page_last               3806
_journal_paper_doi               10.1039/b804294b
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H27 N O3 S'
_chemical_formula_sum            'C20 H27 N O3 S'
_chemical_formula_weight         361.49
_chemical_name_common
;
(+)-3a,5a-Dimethyl-8-(toluene-4-sulfonyl)-
1,3,3a,4,5,5a,6,7,8,9-decahydro-furo(3,4-h)isoquinoline
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.5760(4)
_cell_length_b                   8.40396(10)
_cell_length_c                   9.89489(10)
_cell_measurement_reflns_used    27232
_cell_measurement_temperature    193
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.9
_cell_volume                     1877.34(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      193
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            34420
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         3.92
_exptl_absorpt_coefficient_mu    1.677
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.568
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Higashi, T. (1999). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881 1444 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.008(12)
_refine_ls_extinction_coef       0.0028(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   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.2151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0733
_reflns_number_gt                3314
_reflns_number_total             3420
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b804294b.txt
_cod_data_source_block           I
_cod_database_code               7103288