Rhodium(I)-Catalyzed Cycloisomerization of 1,6-Enynes to Bicyclo[4.1.0]heptenes
Sun Young Kim; Young Keun Chung; Journal of Organic Chemistry 75 (2010) 1281–1284; doi:10.1021/jo902273x

data_4025224
_publ_section_title
;
 Rhodium(I)-Catalyzed Cycloisomerization of 1,6-Enynes to
 Bicyclo[4.1.0]heptenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1281
_journal_page_last               1284
_journal_paper_doi               10.1021/jo902273x
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C21 H23 N O2 S'
_chemical_formula_weight         353.46
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.0340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   16.0988(3)
_cell_length_b                   22.0048(7)
_cell_length_c                   17.5308(5)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     5715.2(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20109
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          1
_exptl_crystal_size_min          0.5
_refine_diff_density_max         1.087
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.205
_refine_ls_extinction_coef       0.0181(19)
_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   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     677
_refine_ls_number_reflns         12641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0882
_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^)+(0.1445P)^2^+3.0007P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2330
_refine_ls_wR_factor_ref         0.2780
_reflns_number_gt                8255
_reflns_number_total             12641
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902273x_si_001.cif
_cod_data_source_block           17enyne
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4025224