A Synthetic Alternative to the Type-II Intramolecular 4 + 3 Cycloaddition Reaction
Richard S. Grainger; Richard B. Owoare; Patrizia Tisselli; Jonathan W. Steed; Journal of Organic Chemistry 68 (2003) 7899–7902; doi:10.1021/jo034356f

data_4022456
_publ_section_title
;
 A Synthetic Alternative to the Type-II Intramolecular
 4 + 3 Cycloaddition Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7899
_journal_page_last               7902
_journal_paper_doi               10.1021/jo034356f
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C11 H14 O2'
_chemical_formula_weight         178.22
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.876(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.1341(6)
_cell_length_b                   7.6802(3)
_cell_length_c                   11.0101(3)
_cell_measurement_temperature    120(2)
_cell_volume                     1781.30(10)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.885
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_device_type  'Nonis KappaCCD CCD diffractometer'
_diffrn_measurement_method       'phi & omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2933
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.59
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9735
_exptl_absorpt_correction_T_min  0.9315
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.021(3)
_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_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+1.2353P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                1548
_reflns_number_total             1813
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034356fsi20030318_091819.cif
_cod_data_source_block           C:\structs\Grainger\ro289a\RO289A.CIF
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4022456