Photoinduced [2+2] cycloadditions (the Paterno–Büchi reaction) of 1-acetylisatin with enol ethers—regioselectivity, diastereoselectivity and acid catalysed transformations of the spirooxetane products
Zhang, Yan; Xue, Jie; Gao, Yi; Fun, Hoong-Kun; Xu, Jian-Hua; Journal of the Chemical Society, Perkin Transactions 1  (2002) 345–353; doi:10.1039/b109697d

data_7204304
_publ_section_title
;
 Photoinduced [2+2] cycloadditions (the Paterno--B\"uchi reaction) of
 1-acetylisatin with enol ethers---regioselectivity, diastereoselectivity
 and acid catalysed transformations of the spirooxetane products
;
_journal_coden_ASTM              JCSPCE
_journal_issue                   3
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              345
_journal_page_last               353
_journal_paper_doi               10.1039/b109697d
_journal_year                    2002
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.046(2)
_cell_angle_beta                 105.633(2)
_cell_angle_gamma                101.122(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2141(8)
_cell_length_b                   8.7676(8)
_cell_length_c                   12.0117(11)
_cell_measurement_reflns_used    1749
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      1.85
_cell_volume                     776.65(13)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method       '\w 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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.1095
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4387
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.051(12)
_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   0.963
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1514
_refine_ls_R_factor_gt           0.0835
_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^)+(0.1397P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2189
_refine_ls_wR_factor_ref         0.2592
_reflns_number_gt                1305
_reflns_number_total             2676
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            b109697d.txt
_cod_data_source_block           compound17
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204304