Simple and efficient syntheses of 2-hydroxy-3H-phenoxazin-3-ones by aerobic oxidative cross-cyclocondensation in water
Li, Wenhao; Duan, Wenxue; Tang, Qingxuan; Li, Zhan-Ting; Yang, Guanyu; Green Chemistry 23 (2021) 1136–1139; doi:10.1039/D0GC03861J

data_7242071
_publ_section_title
;
 Simple and efficient syntheses of 2-hydroxy-3H-phenoxazin-3-ones by
 aerobic oxidative cross-cyclocondensation in water
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              1136
_journal_page_last               1139
_journal_paper_doi               10.1039/D0GC03861J
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C13 H9 N O3'
_chemical_formula_sum            'C13 H9 N O3'
_chemical_formula_weight         227.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-28 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                71.388(14)
_cell_angle_beta                 80.879(14)
_cell_angle_gamma                66.502(17)
_cell_formula_units_Z            2
_cell_length_a                   7.6718(15)
_cell_length_b                   7.8925(13)
_cell_length_c                   10.0037(14)
_cell_measurement_reflns_used    1036
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.2940
_cell_measurement_theta_min      4.6420
_cell_volume                     526.10(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -108.00 -32.00   1.00    2.00    --  -33.50 178.00-150.00   76
  2  \w   -102.00 -15.00   1.00    2.00    --  -33.50 -57.00-180.00   87
  3  \w    -81.00  14.00   1.00    2.00    --  -33.50 112.00  -9.00   95
  4  \w   -108.00 -32.00   1.00    2.00    --  -33.50 178.00 150.00   76
  5  \w    -71.00  39.00   1.00    2.00    --  -33.50  19.00   0.00  110
  6  \w     14.00 107.00   1.00    2.00    --   36.47  37.00-180.00   93
  7  \w     -4.00  77.00   1.00    2.00    --   36.47 -99.00-180.00   81
  8  \w      8.00 106.00   1.00    2.00    --   36.47  77.00  60.00   98
  9  \w     57.00 110.00   1.00    2.00    --   36.47 178.00  30.00   53
 10  \w     38.00 110.00   1.00    2.50    --  108.00 -94.00 150.00   72
 11  \w     38.00 110.00   1.00    2.50    --  108.00 -94.00 -90.00   72
 12  \w     82.00 178.00   1.00    2.50    --  108.00  30.00 -30.00   96
 13  \w     38.00 128.00   1.00    2.50    --  108.00 -45.00 150.00   90
 14  \w     40.00 128.00   1.00    2.50    --  108.00 -61.00 -60.00   88
 15  \w    100.00 178.00   1.00    2.50    --  108.00 111.00 -60.00   78
 16  \w     96.00 133.00   1.00    2.50    --  108.00  77.00  90.00   37
 17  \w     52.00 119.00   1.00    2.50    --  108.00 -61.00-120.00   67
 18  \w     40.00 119.00   1.00    2.50    --  108.00 -45.00  30.00   79
 19  \w     63.00 107.00   1.00    2.50    --  108.00-111.00  90.00   44
 20  \w     79.00 105.00   1.00    2.50    --  108.00 -94.00 -30.00   26
 21  \w     90.00 177.00   1.00    2.50    --  108.00  30.00  60.00   87
 22  \w     88.00 155.00   1.00    2.50    --  108.00  61.00   0.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1342119000
_diffrn_orient_matrix_UB_12      0.1314071000
_diffrn_orient_matrix_UB_13      0.0888879000
_diffrn_orient_matrix_UB_21      -0.0418556000
_diffrn_orient_matrix_UB_22      0.1741118000
_diffrn_orient_matrix_UB_23      -0.1327415000
_diffrn_orient_matrix_UB_31      -0.1680593000
_diffrn_orient_matrix_UB_32      -0.0406716000
_diffrn_orient_matrix_UB_33      -0.0303017000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3745
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.667
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0084(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0708P)^2^+0.0206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1481
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1195
_reflns_number_total             1874
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc03861j2.cif
_cod_data_source_block           20200637
_cod_depositor_comments
'Adding full bibliography for 7242065--7242072.cif.'
_cod_database_code               7242071
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4Cl1
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.847
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C4(H4), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              94854
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.687
_oxdiff_exptl_absorpt_empirical_full_min 0.770