Oxidative radical skeletal rearrangement induced by molecular oxygen: synthesis of quinazolinones.
Wang, Yi-Feng; Zhang, Feng-Lian; Chiba, Shunsuke; Organic letters 15 (2013) 2842–2845; doi:10.1021/ol4011745

data_1512107
_publ_contact_author
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Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
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_publ_section_title
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 Oxidative radical skeletal rearrangement induced by molecular oxygen:
 synthesis of quinazolinones.
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_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2842
_journal_page_last               2845
_journal_paper_doi               10.1021/ol4011745
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C21 H16 N2 O'
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_formula_weight         312.36
_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                 112.371(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.8881(8)
_cell_length_b                   29.449(3)
_cell_length_c                   11.4581(11)
_cell_measurement_reflns_used    4223
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      30.24
_cell_measurement_theta_min      2.37
_cell_volume                     3085.4(5)
_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      103(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32968
_diffrn_reflns_theta_full        30.62
_diffrn_reflns_theta_max         30.62
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         9455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0871P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1654
_reflns_number_gt                6312
_reflns_number_total             9455
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4011745_si_002.cif
_cod_data_source_block           2a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1512107