Preparation of zwitterionic hydroquinone-fused [1,4]oxazinium derivatives via a photoinduced intramolecular dehydrogenative-coupling reaction.
Yi, Chenyi; Liu, Shi-Xia; Neels, Antonia; Renaud, Philippe; Decurtins, Silvio; Organic letters 11 (2009) 5530–5533; doi:10.1021/ol902355b

data_1504298
_publ_section_title
;
 Preparation of zwitterionic hydroquinone-fused [1,4]oxazinium derivatives
 via a photoinduced intramolecular dehydrogenative-coupling reaction.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5530
_journal_page_last               5533
_journal_paper_doi               10.1021/ol902355b
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C14 H12 N4 O4'
_chemical_formula_weight         300.28
_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                94.192(17)
_cell_angle_beta                 104.400(17)
_cell_angle_gamma                104.893(18)
_cell_formula_units_Z            2
_cell_length_a                   8.0209(18)
_cell_length_b                   8.5834(19)
_cell_length_c                   10.689(2)
_cell_measurement_reflns_used    3294
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      1.98
_cell_volume                     681.4(3)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_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  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5368
_diffrn_reflns_theta_full        25.14
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.864
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0495P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0896
_reflns_number_gt                1533
_reflns_number_total             2380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902355b_si_002.cif
_cod_data_source_block           y337
_cod_database_code               1504298