Efficient synthesis of bibutenolide derivatives through oxidative dimeric cyclization-coupling reaction of 2,3-allenoic acids.
Ma, Shengming; Yu, Zhanqian; Organic letters 5 (2003) 1507–1510; doi:10.1021/ol0342812

data_1507290
_publ_section_title
;
 Efficient synthesis of bibutenolide derivatives through oxidative dimeric
 cyclization-coupling reaction of 2,3-allenoic acids.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1507
_journal_page_last               1510
_journal_paper_doi               10.1021/ol0342812
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C26 H26 O4'
_chemical_formula_weight         402.47
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.3667(12)
_cell_length_b                   29.873(2)
_cell_length_c                   8.5210(6)
_cell_measurement_reflns_used    6364
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.232
_cell_measurement_theta_min      4.691
_cell_volume                     4420.7(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            26942
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.1345
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(7)
_refine_ls_extinction_coef       0.00177(18)
_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   0.851
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     750
_refine_ls_number_reflns         10052
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      0.852
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0853
_reflns_number_gt                6027
_reflns_number_total             10052
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0342812si20030218_091610.cif
_cod_data_source_block           cd22122
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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        4420.6(5)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1507290