A Chiral Acrylate Equivalent for Metal-Free Diels-Alder Reactions: endo-2-Acryloylisoborneol
Palomo, Claudio; Oiarbide, Mikel; García, Jesús M.; González, Alberto; Lecumberri, Ainara; Linden, Anthony; Journal of the American Chemical Society 124 (2002) 10288–10289; doi:10.1021/ja025906e

data_4115102
_publ_contact_author_address
; Departamento de Qu\'imica Org\'anica I
  Facultad de Qu\'imica
  Universidad del Pa\'is Vasco
  Apdo 1072
  E-20080 San Sebasti\'an
  Spain
;
_publ_contact_author_email       alinden@oci.unizh.ch
_publ_contact_author_fax         '41 1 635 6812'
_publ_contact_author_name        'Claudio Palomo'
_publ_contact_author_phone       '41 1 635 4228'
_publ_section_title
;
 A Chiral Acrylate Equivalent for Metal-Free Diels-Alder Reactions:
 endo-2-Acryloylisoborneol
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10288
_journal_page_last               10289
_journal_paper_doi               10.1021/ja025906e
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C18 H26 O2 '
_chemical_formula_sum            'C18 H26 O2'
_chemical_formula_weight         274.40
_chemical_melting_point          375(1)
_chemical_name_systematic
; (1R)-2-endo-[(1R,2R,4R)-bicyclo[2.2.1]hept-5-en-2-ylcarbonyl]-1,7,7-
trimethylbicyclo[2.2.1]heptan-2-ol
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90.0
_cell_angle_beta                 90.699(1)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   10.5240(2)
_cell_length_b                   7.1324(2)
_cell_length_c                   20.2579(5)
_cell_measurement_reflns_used    2901
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     1520.47(6)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'TEXCIF (Linden, 1999)'
_computing_structure_refinement
'teXsan (Molecular Structure Corporation, 1999)'
_computing_structure_solution    'SIR92 direct methods (Altomare et al., 1994)'
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 '65 mm CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 1.718
_diffrn_measured_fraction_theta_max 1.718
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\w scans with \k offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24912
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.0757
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details
; The enantiomer used in the refinement was based on the known 
configuration of the camphor moiety.
;
_refine_ls_extinction_coef       0.0000055(6)
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   2.3930
_refine_ls_goodness_of_fit_ref   2.5170
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     369
_refine_ls_number_reflns         4417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     '1/[^2^(F~o~) + (0.005F~o~)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0470
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0462
_reflns_number_gt                4417
_reflns_number_total             5009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja025906e_s2_2.cif
_cod_data_source_block           endo-12c
_cod_original_formula_sum        'C18 H26 O2 '
_cod_database_code               4115102