One-Step Transformation of Tricyclopentabenzene (Trindane, C15H18) to Bicyclo(10.3.0)pentadec-1(12)ene- 2,6,7,11-tetrone (C15H18O4) and Its Aldol Product, 12-Hydroxy-16-oxatetracyclo(10.3.1.0.1,507,11)hexadec-7(11)ene-2,6-dione (C15H18O4)⊥
Ranganathan, Subramania; Muraleedharan, K. M.; Rao, CH. Chandrashekhar; Vairamani, M.; Karle, Isabella L.; Organic Letters 3 (2001) 2447–; doi:10.1021/ol010086g

data_1507508
_publ_section_title
;
 One-Step Transformation of Tricyclopentabenzene (Trindane, C15H18) to
 Bicyclo(10.3.0)pentadec-1(12)ene- 2,6,7,11-tetrone (C15H18O4) and Its
 Aldol Product,
 12-Hydroxy-16-oxatetracyclo(10.3.1.0.1,507,11)hexadec-7(11)ene-2,6-dione
 (C15H18O4)&#x22A5;
;
_journal_issue                   16
_journal_name_full               'Organic Letters'
_journal_page_first              2447
_journal_paper_doi               10.1021/ol010086g
_journal_volume                  3
_journal_year                    2001
_chemical_compound_source        synthesized
_chemical_formula_structural     'C15 C18 O4'
_chemical_formula_sum            'C15 H18 O4'
_chemical_formula_weight         262.29
_chemical_name_systematic
;12-hydroxy-16-oxatetracyclo(10.3.1.0[1,5]. 0[7,11])hexadec-7(11)ene-2,6-dione 
 ?
;
_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, diff map'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                73.02
_cell_angle_beta                 89.26
_cell_angle_gamma                89.44
_cell_formula_units_Z            8
_cell_length_a                   11.471(1)
_cell_length_b                   14.1580(10)
_cell_length_c                   17.1210(10)
_cell_measurement_temperature    293(2)
_cell_volume                     2659.1(3)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'direct phase determination'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Bruker P4 diffractometer'
_diffrn_measurement_method       'theta-2theta scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7699
_diffrn_reflns_theta_max         57.49
_diffrn_reflns_theta_min         2.70
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.775
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       'thin plates'
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.869
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0028(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_all   1.009
_refine_ls_goodness_of_fit_obs   1.044
_refine_ls_hydrogen_treatment    'riding on C atom to which attached'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     683
_refine_ls_number_reflns         7211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_restrained_S_obs      1.044
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_obs          0.0607
_refine_ls_shift/esd_max         -0.005
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+1.9968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1725
_refine_ls_wR_factor_obs         0.1414
_reflns_number_observed          4855
_reflns_number_total             7213
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ol010086g.cif
_cod_data_source_block           oz4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+1.9968P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+1.9968P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2659.1(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1507508