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_1506980
_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         'C20 H28 O7 '
_chemical_formula_sum            'C20 H28 O7'
_chemical_formula_weight         380.437
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 99.303(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.5630(9)
_cell_length_b                   20.8620(11)
_cell_length_c                   12.5750(4)
_cell_measurement_temperature    298
_cell_volume                     4029.1(3)
_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
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_diffrn_measurement_device       'DIP Image plate'
_diffrn_measurement_method       IP
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.02495
_diffrn_orient_matrix_UB_12      0.07586
_diffrn_orient_matrix_UB_13      -0.00965
_diffrn_orient_matrix_UB_21      0.03931
_diffrn_orient_matrix_UB_22      0.00967
_diffrn_orient_matrix_UB_23      -0.02563
_diffrn_orient_matrix_UB_31      -0.03397
_diffrn_orient_matrix_UB_32      -0.00708
_diffrn_orient_matrix_UB_33      -0.05478
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7198
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_diffrn_reflns_theta_max         25.75
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cube
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.05
_refine_diff_density_min         -0.50
_refine_diff_density_rms         0.08
_refine_ls_extinction_coef       69E5(8)
_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   0.526
_refine_ls_goodness_of_fit_gt    0.552
_refine_ls_goodness_of_fit_ref   0.552
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     550
_refine_ls_number_reflns         5863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.081
_refine_ls_R_factor_gt           0.073
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.005
_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         0.186
_refine_ls_wR_factor_gt          0.184
_refine_ls_wR_factor_ref         0.184
_reflns_d_resolution_high        0.64
_reflns_d_resolution_low         2.08
_reflns_limit_h_max              18
_reflns_limit_h_min              0
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                5864
_reflns_number_total             7422
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_cod_data_source_file            ol0483450si20040820_035617.cif
_cod_data_source_block           14i
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom, diff' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c        '
_cod_original_formula_sum        'C20 H28 O7 '
_cod_database_code               1506980