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_7242067
_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 O4'
_chemical_formula_sum            'C13 H9 N O4'
_chemical_formula_weight         243.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc25t64c
_audit_creation_date             2020-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-30 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.682(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.1572(5)
_cell_length_b                   11.7989(2)
_cell_length_c                   6.85220(14)
_cell_measurement_reflns_used    2207
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7590
_cell_measurement_theta_min      4.0740
_cell_volume                     2168.92(7)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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   -104.00 -11.00   0.50    4.00    --  -33.50 -37.00 -90.00  186
  2  \w   -108.00 -32.00   0.50    4.00    --  -33.50 178.00  30.00  152
  3  \w    -71.00  39.00   0.50    4.00    --  -33.50  19.00  90.00  220
  4  \w     30.00 103.00   0.50    4.00    --   36.47-143.00 144.00  146
  5  \w      8.00 106.00   0.50    4.00    --   36.47  77.00   0.00  196
  6  \w     18.00 105.00   0.50    4.00    --   36.47  57.00-180.00  174
  7  \w     -4.00  77.00   0.50    4.00    --   36.47 -99.00 -60.00  162
  8  \w     -4.00  77.00   0.50    4.00    --   36.47 -99.00-180.00  162
  9  \w     57.00 110.00   0.50    4.00    --   36.47 178.00 -30.00  106
 10  \w     57.00 110.00   0.50    4.00    --   36.47 178.00   0.00  106
 11  \w     63.00 178.00   0.50   13.00    --  108.00  15.00-120.00  230
 12  \w     38.00  64.00   0.50   13.00    --  108.00-111.00-150.00   52
 13  \w     37.00 112.00   0.50   13.00    --  108.00-111.00 120.00  150
 14  \w     89.00 172.00   0.50   13.00    --  108.00  61.00 -60.00  166
 15  \w     66.00 110.00   0.50   13.00    --  108.00 -94.00 -60.00   88
 16  \w     38.00 108.00   0.50   13.00    --  108.00 -45.00-120.00  140
 17  \w     58.00 108.00   0.50   13.00    --  108.00-111.00 -90.00  100
 18  \w    110.00 171.00   0.50   13.00    --  108.00 111.00 -90.00  122
 19  \w     40.00 126.00   0.50   13.00    --  108.00 -45.00 -60.00  172
 20  \w     83.00 141.00   0.50   13.00    --  108.00  30.00  30.00  116
 21  \w     66.00  92.00   0.50   13.00    --  108.00-111.00-150.00   52
 22  \w    100.00 137.50   0.50   13.00    --  108.00 111.00-120.00   75
;
_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      -0.0568185000
_diffrn_orient_matrix_UB_12      -0.0179017000
_diffrn_orient_matrix_UB_13      -0.0602745000
_diffrn_orient_matrix_UB_21      0.0076692500
_diffrn_orient_matrix_UB_22      -0.1290811500
_diffrn_orient_matrix_UB_23      -0.0066251000
_diffrn_orient_matrix_UB_31      0.0032555500
_diffrn_orient_matrix_UB_32      -0.0085289500
_diffrn_orient_matrix_UB_33      0.2280058000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6615
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         3.295
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71318
_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    1.490
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00033(8)
_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   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.5077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1430
_reflns_number_total             1928
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc03861j2.cif
_cod_data_source_block           202007112
_cod_depositor_comments
'Adding full bibliography for 7242065--7242072.cif.'
_cod_database_code               7242067
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C14H15N2O4
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.871
_reflns_odcompleteness_completeness 99.66
_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(H1A), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              36246
_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 1.622
_oxdiff_exptl_absorpt_empirical_full_min 0.850