Diazaphenoxazines and Diazaphenothiazines: Synthesis of the "Correct" Isomers Reveals They Are Highly Reactive Radical-Trapping Antioxidants.
Haidasz, Evan A.; Pratt, Derek A.; Organic letters 19 (2017) 1854–1857; doi:10.1021/acs.orglett.7b00615

data_1545944
_publ_section_title
;
 Diazaphenoxazines and Diazaphenothiazines: Synthesis of the
 &quot;Correct&quot; Isomers Reveals They Are Highly Reactive
 Radical-Trapping&#x00A0;Antioxidants.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1854
_journal_page_last               1857
_journal_paper_doi               10.1021/acs.orglett.7b00615
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C14 H14 N4 S'
_chemical_formula_weight         270.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.71(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.013(3)
_cell_length_b                   5.4697(17)
_cell_length_c                   11.876(4)
_cell_measurement_reflns_used    1305
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.94
_cell_measurement_theta_min      2.52
_cell_volume                     646.0(4)
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4861
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.475
_diffrn_reflns_theta_min         1.726
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       needle
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.710
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 491 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2114
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.2206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.591
_reflns_Friedel_fraction_full    0.752
_reflns_Friedel_fraction_max     0.738
_reflns_number_gt                1534
_reflns_number_total             2114
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00615_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               1545944
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.847
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              43212
_shelx_hkl_checksum              47141