Formation of 2-oxa- or 2-azabicyclo[3.3.0]octa-3,7-diene by a novel tandem intramolecular photo-cyclization of 2,4,6-tris(phenylthio)hepta-2,4,6-trienal derivatives
Yoshimatsu, Mitsuhiro; Gotoh, Satoshi; Tanabe, Genzoh; Muraoka, Osamu; Chemical Communications  (1999) 909–; doi:10.1039/a901707k

data_7110515
_publ_contact_author
; Mitsuhiro Yoshimatsu

Faculty of Education

Gifu University

1-1 Yanagido

Gifu 501-1193

Japan

;
_publ_section_title
;
 Formation of 2-oxa- or 2-azabicyclo[3.3.0]octa-3,7-diene by a novel
 tandem intramolecular photo-cyclization of
 2,4,6-tris(phenylthio)hepta-2,4,6-trienal derivatives
;
_journal_issue                   10
_journal_name_full               'Chemical Communications'
_journal_page_first              909
_journal_paper_doi               10.1039/a901707k
_journal_year                    1999
_chemical_compound_source
; 

An acetonitrile solution (1400 ml) solution of (2E,4E,6E)-2,4,6-

tris(phenylthio)nona-2,4,6-trienal 1 (1.80 g, 3.68 mmol) was irradiated by
a 40W 

fluorecent daylight lamp for 3 days.  The solvent was removed under reduced
pressure.

The residue was purified by preparative TLC on eluting with AcOEt-hexane (1:40)

to afford
(1R*,5R*,6S*)-6-t-butyl-1,4,7-tris(phenylthio)-2-oxabicyclo[3.3.0]octa-

3,7-diene (2) (0.98 g, 54%) as colorless prisms.

;
_chemical_formula_moiety         'C29 H28 O S3'
_chemical_formula_sum            'C29 H28 O S3'
_chemical_formula_weight         488.72
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source
;International Tables for X-ray Crystallography Vol.IV

;
_cell_angle_alpha                90.02(2)
_cell_angle_beta                 99.34(2)
_cell_angle_gamma                89.99(2)
_cell_formula_units_Z            4
_cell_length_a                   9.007(2)
_cell_length_b                   26.879(6)
_cell_length_c                   10.945(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      -90.0
_cell_measurement_theta_min      90.0
_cell_volume                     2614.6(10)
_computing_cell_refinement
; MSC/AFC Diffractometer Control Software(Molecular Structure 

Corporation, 1988)

;
_computing_data_collection
;MSC/AFC Diffractometer Control Software(Molecular Structure

 Corporation, 1988)

;
_computing_data_reduction
; TEXSAN. TEXRAY Structure Analysis Package (Molecular Srtucture 

Corporation, 1985)

;
_computing_molecular_graphics
;ORTEPII(Johnson, 1976)

;
_computing_structure_refinement
; TEXSAN. TEXRAY Structure Analysis Package (Molecular Structure 

Corporation, 1985)

;
_computing_structure_solution
;MITHRIL90 (Gilmore,1990) & DIRDIF (Beurskens, 1984)

;
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       IW-2Iq
_diffrn_radiation_type           CuIKa
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            4284
_diffrn_reflns_theta_max         60.0720
_diffrn_standards_decay_%        26.13
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    27.28
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   3.28
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     298
_refine_ls_number_reflns         2521
_refine_ls_R_factor_obs          0.056
_refine_ls_shift/esd_max         0.00
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4F~o~^2^/IS^2^(F~o~^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.070
_reflns_number_observed          2720
_reflns_number_total             4096
_reflns_observed_criterion       I>3.00IS(I)
_cod_data_source_file            901707ksup1.cif
_cod_data_source_block           1
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 4F~o~^2^/IS^2^(F~o~^2^)' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
4F~o~^2^/IS^2^(F~o~^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2614.7(9)
_cod_original_sg_symbol_H-M      'P2~1~/n '
_cod_database_code               7110515