Complete Control of Regioselectivity in the Intramolecular [2 + 2] Photocycloaddition of 2-Alkenyl-3(2H)-furanones by the Length of the Side Chain
Thorsten Bach; Michael Kemmler; Eberhardt Herdtweck; Journal of Organic Chemistry 68 (2003) 1994–1997; doi:10.1021/jo0264372

data_4022300
_publ_contact_author
;
       Dr. Eberhardt Herdtweck
       Anorganisch-chemisches Institut der
       Technischen Universit\"at M\"unchen,
       Lichtenbergstrasse 4,
       D-85747 Garching bei M\"unchen,
       Germany.
;
_publ_contact_author_email       eberhardt.herdtweck@ch.tum.de
_publ_contact_author_fax         ' +49(0)89 289 13473'
_publ_contact_author_phone       '+49(0)89 289 13143'
_publ_section_title
;
 Complete Control of Regioselectivity in the Intramolecular
 [2 + 2] Photocycloaddition of 2-Alkenyl-3(2H)-furanones
 by the Length of the Side Chain
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1994
_journal_page_last               1997
_journal_paper_doi               10.1021/jo0264372
_journal_volume                  68
_journal_year                    2003
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C17 H18 O4'
_chemical_formula_sum            'C17 H18 O4'
_chemical_formula_weight         286.31
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             10-Sep-02
_audit_creation_method           'PLATON <TABLE ACC> option'
_audit_update_record
;
  10-Sep-02  Updated by the Author E.H.
            Textwriting by E.H.
            Checkcif    OK
  11-Sep-02  Updated by the Author E.H.
;
_cell_angle_alpha                68.44(3)
_cell_angle_beta                 84.42(2)
_cell_angle_gamma                69.68(3)
_cell_formula_units_Z            2
_cell_length_a                   7.408(2)
_cell_length_b                   10.275(5)
_cell_length_c                   10.768(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      48.6
_cell_measurement_theta_min      38.0
_cell_volume                     714.4(5)
_computing_cell_refinement       'CAD4 (Straver, 1989'
_computing_data_collection       'CAD4 (Straver, 1989)'
_computing_data_reduction        'MoleN(Fair, 1990)'
_computing_molecular_graphics    'PLATON PLUTON (Spek, 2001)'
_computing_publication_material  'PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1998)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector                 'scintillation counter'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'CAD4 (Nonius)'
_diffrn_measurement_method       'theta/2theta scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'NONIUS FR 590 sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5579
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        7.6
_diffrn_standards_interval_count 60
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
; 
 no correction applied
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       fragment
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.97
_exptl_crystal_size_mid          0.72
_exptl_crystal_size_min          0.64
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.2037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                2406
_reflns_number_total             2795
_reflns_threshold_expression     >2sigma(i)
_cod_data_source_file            jo0264372si20021203_024615.cif
_cod_data_source_block           KEMC-1022-153
_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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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 
;
_cod_database_code               4022300