Synthesis and Structural Investigation of an "Oxazinoquinolinespirohexadienone" That Only Exists as Its Long-Wavelength Ring-Opened Quinonimine Isomer
Benjamin J. Pollock; Christos A. Sikes; Ryan P. Ter Louw; Scott R. Hawken; Amy L. Speelman; Eugene J. Lynch; Daniel J. Stanford; Kraig A. Wheeler; Jason G. Gillmore; Journal of Organic Chemistry 77 (2012) 8689–8695; doi:10.1021/jo3016083

data_4027565
_publ_section_title
;
 Synthesis and Structural Investigation of an
 "Oxazinoquinolinespirohexadienone" That Only Exists as Its
 Long-Wavelength Ring-Opened Quinonimine Isomer
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8689
_journal_page_last               8695
_journal_paper_doi               10.1021/jo3016083
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C11 H11 N O'
_chemical_formula_sum            'C11 H11 N O'
_chemical_formula_weight         173.21
_chemical_name_systematic
; 
 ? 
;
_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                 90.870(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2964(2)
_cell_length_b                   11.3994(3)
_cell_length_c                   9.5886(3)
_cell_measurement_reflns_used    5674
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.517
_cell_measurement_theta_min      3.650
_cell_volume                     906.73(4)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12329
_diffrn_reflns_theta_full        67.78
_diffrn_reflns_theta_max         67.78
_diffrn_reflns_theta_min         6.03
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  0.8299
_exptl_absorpt_correction_T_min  0.7490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       'transparent rhomboid'
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1638
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0537P)^2^+0.2090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                1488
_reflns_number_total             1638
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3016083_si_004.cif
_cod_data_source_block           c:\frames\guest\jgg03\work\jgg03
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027565