Double-Tandem [4π+2π].[2π+2π].[4π+2π].[2π+2π] Synthetic Sequence with Photoprotolytic Oxametathesis and Photoepoxidation in the Chromone Series
Roman A. Valiulin; Teresa M. Arisco; Andrei G. Kutateladze; Journal of Organic Chemistry 76 (2011) 1319–1332; doi:10.1021/jo102221q

data_4026072
_publ_contact_author_address
;Department of Chemistry and Biochemistry
University of Denver
FW Olin Hall, 202
2190 E. Iliff Ave
Denver, CO 80208
;
_publ_contact_author_email       akutatel.edu
_publ_contact_author_fax         303-871-2254
_publ_contact_author_name        'Andrei Kutateladze'
_publ_contact_author_phone       303-871-2995
_publ_section_title
;
 Double-Tandem [4\p+2\p].[2\p+2\p].[4\p+2\p].[2\p+2\p] Synthetic Sequence
 with Photoprotolytic Oxametathesis and Photoepoxidation in the Chromone
 Series
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1319
_journal_page_last               1332
_journal_paper_doi               10.1021/jo102221q
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.28
_chemical_name_common            none
_chemical_name_systematic
;
exo-4,5-benzo-7-cyano-3-oxatricyclo[6.2.2.0^2,7^]dodec-9-ene-6-one
;
_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                89.4910(10)
_cell_angle_beta                 81.1990(10)
_cell_angle_gamma                66.46
_cell_formula_units_Z            2
_cell_length_a                   6.70800(10)
_cell_length_b                   7.86520(10)
_cell_length_c                   12.7175(2)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.83
_cell_volume                     606.881(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 APEX II Diffractometer'
_diffrn_measurement_method       '\f and \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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0097
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25717
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_correction_T_min  0.9403
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       needle
_exptl_crystal_F_000             266
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.695
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.695
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1503P)^2^+0.2498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1602
_reflns_number_gt                2573
_reflns_number_total             2896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102221q_si_003.cif
_cod_data_source_block           rav28591
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4026072