Rhodium-catalyzed one-pot intermolecular [2 + 2 + 2] trimerization/asymmetric intramolecular [4 + 2] cycloaddition of two aryl ethynyl ethers and 5-alkynals.
Miyauchi, Yuta; Noguchi, Keiichi; Tanaka, Ken; Organic letters 14 (2012) 5856–5859; doi:10.1021/ol3027158

data_1508759
_publ_section_title
;
 Rhodium-catalyzed one-pot intermolecular [2 + 2 + 2]
 trimerization/asymmetric intramolecular [4 + 2] cycloaddition of two aryl
 ethynyl ethers and 5-alkynals.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5856
_journal_page_last               5859
_journal_paper_doi               10.1021/ol3027158
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H37 N O5 S, 0.5(C6 H14)'
_chemical_formula_sum            'C43 H44 N O5 S'
_chemical_formula_weight         686.85
_chemical_name_systematic
;
 (-)-4-Butyl-6-(naphthalen-2-yloxy)-2-(toluene-4-sulfonyl)-2,3,5,7a-
 tetrahydro-1H-isoindole-5-carboxylic acid naphthalen-2-yl ester
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.195(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.5752(10)
_cell_length_b                   8.5637(4)
_cell_length_c                   20.8927(10)
_cell_measurement_reflns_used    19118
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.09
_cell_measurement_theta_min      4.23
_cell_volume                     3681.3(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2004)'
_computing_data_reduction        'RAPID AUTO'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS 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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34695
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         4.23
_exptl_absorpt_coefficient_mu    1.148
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1460
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881  3112 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       0.0022(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   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         6735
_refine_ls_number_restraints     301
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0739
_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^)+(0.1556P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.2468
_reflns_number_gt                3352
_reflns_number_total             6735
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3027158_si_001.cif
_cod_data_source_block           I
_cod_database_code               1508759