Palladium catalysed [2 + 2 + 1] intramolecular cycloaddition for the preparation of bicyclo[3.3.0]octa-1.5-dien-3-ones from 1,6-diynes
Grigg, Ronald; Zhang, Lixin; Collard, Simon; Keep, Ann; Chemical Communications (Cambridge, United Kingdom)  (2003) 1902–1903; doi:10.1039/b302841k

data_7103804
_publ_section_title
;
 Palladium catalysed [2 + 2 + 1] intramolecular cycloaddition for the
 preparation of bicyclo[3.3.0]octa-1.5-dien-3-ones from 1,6-diynes
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   15
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1902
_journal_page_last               1903
_journal_paper_doi               10.1039/b302841k
_journal_year                    2003
_chemical_formula_sum            'C12 H12 O5'
_chemical_formula_weight         236.22
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.7220(13)
_cell_angle_beta                 75.5740(13)
_cell_angle_gamma                82.5810(19)
_cell_formula_units_Z            2
_cell_length_a                   5.70010(10)
_cell_length_b                   9.0939(3)
_cell_length_c                   11.3003(4)
_cell_measurement_temperature    150(2)
_cell_volume                     552.52(3)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1996)'
_computing_data_collection
'DENZO-SMN and COLLECT (Otwinowski & Minor, 1996)'
_computing_data_reduction
'DENZO-SMN and COLLECT (Otwinowski & Minor, 1996)'
_computing_molecular_graphics    ORTEX
_computing_publication_material  'WinCIF (Thornton-Pett, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector diffractometer'
_diffrn_measurement_method       'phi-omega scan'
_diffrn_radiation_detector       'CCD plate'
_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  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8959
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        'not measured'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
?
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.42
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.09
_refine_ls_extinction_coef       0.10(2)
_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   1.23
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.23
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0726P)^2^+0.1195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1451
_reflns_number_gt                1760
_reflns_number_total             2146
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b302841k.txt
_cod_data_source_block           z122
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7103804