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_7242069
_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         'C14 H11 N O3'
_chemical_formula_sum            'C14 H11 N O3'
_chemical_formula_weight         241.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 97.187(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.6906(3)
_cell_length_b                   14.7537(9)
_cell_length_c                   16.5416(11)
_cell_measurement_reflns_used    701
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.9800
_cell_measurement_theta_min      4.0090
_cell_volume                     1135.75(13)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -102.00 -15.00   1.00    4.00    --  -33.50 -57.00 -90.00   87
  2  \w   -108.00 -32.00   1.00    4.00    --  -33.50 178.00  90.00   76
  3  \w     44.00  69.00   1.00    4.00    --   36.47 -19.00  30.00   25
  4  \w     59.00  91.00   1.00    4.00    --   36.47 178.00-120.00   32
  5  \w     79.00 109.00   1.00    4.00    --   36.47 178.00-180.00   30
  6  \w     57.00  86.00   1.00    4.00    --   36.47-142.00 111.00   29
  7  \w     76.00 106.00   1.00    4.00    --   36.47 178.00  30.00   30
  8  \w    -36.00  23.00   1.00    4.00    --   36.47 -19.00  30.00   59
  9  \w     39.00 119.00   1.00    7.50    --  108.00 -45.00-150.00   80
 10  \w     55.00 106.00   1.00    7.50    --  108.00-111.00 150.00   51
 11  \w     44.00 128.00   1.00    7.50    --  108.00 -45.00 120.00   84
 12  \w    104.00 149.00   1.00    7.50    --  108.00  45.00  30.00   45
 13  \w     49.00 104.00   1.00    7.50    --  108.00 -45.00  60.00   55
 14  \w     52.00 100.00   1.00    7.50    --  108.00-111.00  30.00   48
 15  \w     52.00 109.00   1.00    7.50    --  108.00 -94.00-150.00   57
 16  \w     82.00 158.00   1.00    7.50    --  108.00  30.00 -60.00   76
;
_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      0.0853924000
_diffrn_orient_matrix_UB_12      -0.0640786000
_diffrn_orient_matrix_UB_13      0.0726029000
_diffrn_orient_matrix_UB_21      0.0043544000
_diffrn_orient_matrix_UB_22      -0.0804814000
_diffrn_orient_matrix_UB_23      -0.0591917000
_diffrn_orient_matrix_UB_31      0.3195462000
_diffrn_orient_matrix_UB_32      0.0182174000
_diffrn_orient_matrix_UB_33      -0.0064075000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4088
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         4.029
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10259
_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    1.411
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0590
_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^)+(0.0724P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1657
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1192
_reflns_number_total             2025
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc03861j2.cif
_cod_data_source_block           20200638
_cod_depositor_comments
'Adding full bibliography for 7242065--7242072.cif.'
_cod_original_cell_volume        1135.74(12)
_cod_database_code               7242069
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4Cl1
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.879
_reflns_odcompleteness_completeness 99.48
_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), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              38870
_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 7.202
_oxdiff_exptl_absorpt_empirical_full_min 0.724