Intramolecular Diels-Alder Reactions of Ester Linked 1,3,9-Decatrienes: Cis/Trans Selectivity in Thermal and Lewis Acid Promoted Reactions of Ethylene-Tethered and Benzo-Tethered Systems
Emma L. Pearson; Laurence C. H. Kwan; Craig I. Turner; Garth A. Jones; Anthony C. Willis; Michael N. Paddon-Row; Michael S. Sherburn; Journal of Organic Chemistry 71 (2006) 6099–6109; doi:10.1021/jo0607818

data_4021845
_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, ACT 0200, Australia
;
_publ_contact_author_email       ' sherburn@rsc.anu.edu.au '
_publ_contact_author_fax         ' 61 2 6125 8114 '
_publ_contact_author_name        ' Michael S. Sherburn '
_publ_contact_author_phone       ' 61 2 6125 4988 '
_publ_section_title
;
 Intramolecular Diels-Alder Reactions of Ester Linked 1,3,9-Decatrienes:
 Cis/Trans Selectivity in Thermal and Lewis Acid Promoted Reactions
 of Ethylene-Tethered and Benzo-Tethered Systems
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6099
_journal_page_last               6109
_journal_paper_doi               10.1021/jo0607818
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source        local
_chemical_formula_moiety         'C15 H14 O4'
_chemical_formula_sum            'C15 H14 O4'
_chemical_formula_weight         258.27
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             06-03-15
_audit_creation_method           CRYSTALS_ver_12.18
_audit_update_record
;
2004-08         Data collected
2006-03-15 - Raw frames reprocessed
2006-03-16 - Report on  C15 H14 O4 
             by Anthony C. Willis
             for Craig Turner and Mick Sherburn
2006-03-16 - passes checkcif tests with minor warnings
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.8162(1)
_cell_length_b                   19.9828(6)
_cell_length_c                   21.1044(6)
_cell_measurement_reflns_used    46769
_cell_measurement_temperature    200
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     2452.84(11)
_computing_cell_refinement       'Denzo/Scalepack '
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek,  2001)'
_computing_publication_material  'CRYSTALS '
_computing_structure_refinement  'CRYSTALS (Watkin et al 2003)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29744
_diffrn_reflns_theta_full        27.476
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         2.808
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1352
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         1828
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.005211
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.414 0.200 0.168 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0612
_refine_ls_wR_factor_gt          0.0389
_refine_ls_wR_factor_ref         0.0389
_reflns_limit_h_max              7
_reflns_limit_h_min              0
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                1828
_reflns_number_total             2813
_reflns_threshold_expression     I>1.5\s(I)
_cod_data_source_file            jo0607818si20060413_123325.cif
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               4021845