Intramolecular pyridone/enyne photocycloaddition: partitioning of the [4 + 4] and [2 + 2] pathways.
Kulyk, Svitlana; Dougherty, Jr, William G; Kassel, W. Scott; Zdilla, Michael J.; Sieburth, Scott McN; Organic letters 13 (2011) 2180–2183; doi:10.1021/ol200390j

data_1502085
_publ_section_title
;
 Intramolecular pyridone/enyne photocycloaddition: partitioning of the [4
 + 4] and [2 + 2] pathways.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2180
_journal_page_last               2183
_journal_paper_doi               10.1021/ol200390j
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         '(C9 H8 N1 O1) (C1 H3)2 (C2 H1) (O)'
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_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                 100.540(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.217(3)
_cell_length_b                   10.848(3)
_cell_length_c                   18.810(5)
_cell_measurement_reflns_used    9418
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.270
_cell_measurement_theta_min      2.198
_cell_volume                     2250.2(11)
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_collection       'COSMO (Bruker-AXS)'
_computing_data_reduction        'SADABS (Bruker-AXS)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'APEX2 (Bruker-AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEX II DUO'
_diffrn_measurement_method       'phi and 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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7701
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 9411 Corrected reflections written to file 
 C:\frames\guest\197\work\mo_197_0m.hkl
 Estimated minimum and maximum transmission:  0.6779  0.7456
 The ratio of these values is more reliable than their absolute values!
 Additional spherical absorption correction applied with mu*r =  0.2000
 Lambda/2 correction factor = 0.0015
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0405P)^2^+1.2960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0955
_reflns_number_gt                1406
_reflns_number_total             1985
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200390j_si_004.cif
_cod_data_source_block           solve_15
_cod_original_cell_volume        2250.3(11)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1502085