Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic beta-keto esters with terminal alkynes.
Kuninobu, Yoichiro; Morita, Junya; Nishi, Mitsumi; Kawata, Atsushi; Takai, Kazuhiko; Organic letters 11 (2009) 2535–2537; doi:10.1021/ol900772h

data_1503952
_publ_section_title
;
 Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a
 reaction of cyclic beta-keto esters with terminal alkynes.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2535
_journal_page_last               2537
_journal_paper_doi               10.1021/ol900772h
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C20 H18 O3 '
_chemical_formula_sum            'C20 H18 O3'
_chemical_formula_weight         306.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.8570(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   27.2828(5)
_cell_length_b                   7.17088(13)
_cell_length_c                   15.7671(3)
_cell_measurement_reflns_used    26988
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.4
_cell_volume                     2952.16(10)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR2004
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34111
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296.00
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.89
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     419
_refine_ls_number_reflns         5374
_refine_ls_R_factor_gt           0.0713
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1396P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1949
_reflns_number_gt                4262
_reflns_number_total             5374
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol900772h_si_002.cif
_cod_data_source_block           '_sc0330'
_cod_original_cell_volume        2952.16(9)
_cod_original_formula_sum        'C20 H18 O3 '
_cod_database_code               1503952