[2 + 2] Photochemical Cycloaddition/Ring Opening of 6-Alkenyl-2,3-dihydro-4-pyridones
James J. Sahn; Daniel L. Comins; Journal of Organic Chemistry 75 (2010) 6728–6731; doi:10.1021/jo101276q

data_4025702
_publ_section_title
;
 [2 + 2] Photochemical Cycloaddition/Ring Opening of
 6-Alkenyl-2,3-dihydro-4-pyridones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6728
_journal_page_last               6731
_journal_paper_doi               10.1021/jo101276q
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C19 H33 N O3'
_chemical_formula_weight         323.46
_chemical_name_systematic
;2-Isopropyl-7-methyl-4-oxo-1-aza-
 spiro[5.5]undecane-1-carboxylic acid tert-butyl ester
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.663(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2852(3)
_cell_length_b                   10.9825(4)
_cell_length_c                   18.1638(6)
_cell_measurement_reflns_used    2851
_cell_measurement_temperature    110
_cell_measurement_theta_max      68.79
_cell_measurement_theta_min      4.71
_cell_volume                     1850.25(11)
_computing_cell_refinement       SAINT
_computing_data_collection       Apex2
_computing_data_reduction        SAINT
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py
_computing_structure_refinement  XL
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      110
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Apex2'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12960
_diffrn_reflns_theta_full        69.59
_diffrn_reflns_theta_max         69.59
_diffrn_reflns_theta_min         4.71
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  0.9473
_exptl_absorpt_correction_T_min  0.8244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0489P)^2^+0.1659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                2781
_reflns_number_total             3436
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101276q_si_001.cif
_cod_data_source_block           x09058
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4025702