Thermal and palladium-catalyzed [3 + 2] synthesis of cyclopentadienone acetals from cyclopropenone acetals and acetylenes.
Isobe, Hiroyuki; Sato, Sota; Tanaka, Takatsugu; Tokuyama, Hidetoshi; Nakamura, Eiichi; Organic letters 6 (2004) 3569–3571; doi:10.1021/ol0483450

data_1506986
_publ_section_title
;
 Thermal and palladium-catalyzed [3 + 2] synthesis of cyclopentadienone
 acetals from cyclopropenone acetals and acetylenes.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              3569
_journal_page_last               3571
_journal_paper_doi               10.1021/ol0483450
_journal_volume                  6
_journal_year                    2004
_chemical_compound_source        'Nakamura laboratory'
_chemical_formula_moiety         'C27 H30 O6 '
_chemical_formula_sum            'C27 H30 O6'
_chemical_formula_weight         450.531
_chemical_name_systematic
;
 ?
;
_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           maXus
_cell_angle_alpha                94.578(4)
_cell_angle_beta                 99.652(5)
_cell_angle_gamma                104.643(5)
_cell_formula_units_Z            2
_cell_length_a                   9.9730(5)
_cell_length_b                   11.3770(10)
_cell_length_c                   10.8700(10)
_cell_measurement_temperature    298
_cell_volume                     1166.70(16)
_computing_cell_refinement       Scalepack(HKL)
_computing_data_collection       'DIP Image plate'
_computing_data_reduction        'maXus (Mackay et al., 1999)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_publication_material  'maXus(Mackay et al., 1999)'
_computing_structure_refinement  'maXus(Mackay et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_measurement_device       'DIP Image plate'
_diffrn_measurement_method       IP
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.02315
_diffrn_orient_matrix_UB_12      -0.10068
_diffrn_orient_matrix_UB_13      -0.01981
_diffrn_orient_matrix_UB_21      0.02764
_diffrn_orient_matrix_UB_22      -0.00230
_diffrn_orient_matrix_UB_23      -0.08643
_diffrn_orient_matrix_UB_31      0.09217
_diffrn_orient_matrix_UB_32      -0.00124
_diffrn_orient_matrix_UB_33      0.01664
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3832
_diffrn_reflns_theta_full        25.73
_diffrn_reflns_theta_max         25.73
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cube
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.74
_refine_diff_density_min         -0.80
_refine_diff_density_rms         0.21
_refine_ls_extinction_coef       36E5(12)
_refine_ls_extinction_expression
;
 equation(22) p292 'Crystallographic Computing' (1970)
 coefficient is multiplied by 10^4
;
_refine_ls_extinction_method     Zachariasen
_refine_ls_goodness_of_fit_all   1.142
_refine_ls_goodness_of_fit_gt    1.242
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.173
_refine_ls_R_factor_gt           0.167
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details     ' w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.486
_refine_ls_wR_factor_gt          0.486
_refine_ls_wR_factor_ref         0.486
_reflns_d_resolution_high        0.64
_reflns_d_resolution_low         2.04
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              12
_reflns_limit_l_min              -13
_reflns_number_gt                3290
_reflns_number_total             3947
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_cod_data_source_file            ol0483450si20040820_035617.cif
_cod_data_source_block           19
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1166.7(2)
_cod_original_sg_symbol_H-M      'P -1          '
_cod_original_formula_sum        'C27 H30 O6 '
_cod_database_code               1506986