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_7242066
_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         'C2 H6 O S, C12 H6 F N O3'
_chemical_formula_sum            'C14 H12 F N O4 S'
_chemical_formula_weight         309.31
_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     direct
_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                97.694(6)
_cell_angle_beta                 93.323(7)
_cell_angle_gamma                97.422(9)
_cell_formula_units_Z            2
_cell_length_a                   6.1820(7)
_cell_length_b                   7.3430(7)
_cell_length_c                   15.4344(9)
_cell_measurement_reflns_used    1538
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8470
_cell_measurement_theta_min      5.7960
_cell_volume                     686.49(11)
_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    'ShelXS (Sheldrick, 2008)'
_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   -105.00  38.00   1.00    1.00    --  -33.50   0.00 150.00  143
  2  \w    -56.00  37.00   1.00    1.00    --  -33.50  37.00-180.00   93
  3  \w   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00   0.00   93
  4  \w     -4.00  77.00   1.00    1.00    --   36.47 -99.00-180.00   81
  5  \w     -4.00  77.00   1.00    1.00    --   36.47 -99.00 -30.00   81
  6  \w     57.00 110.00   1.00    1.00    --   36.47 178.00-180.00   53
  7  \w     57.00 110.00   1.00    1.00    --   36.47 178.00 -90.00   53
  8  \w     57.00 110.00   1.00    1.00    --   36.47 178.00 -30.00   53
  9  \w      8.00 106.00   1.00    1.00    --   36.47  77.00 -60.00   98
 10  \w     40.00 128.00   1.00    1.00    --  108.00 -61.00-120.00   88
 11  \w     37.00 134.00   1.00    1.00    --  108.00 -30.00  60.00   97
 12  \w    100.00 175.00   1.00    1.00    --  108.00 111.00  60.00   75
 13  \w     38.00 110.00   1.00    1.00    --  108.00 -45.00 -60.00   72
 14  \w     89.00 167.00   1.00    1.00    --  108.00  61.00-120.00   78
 15  \w     62.00 100.00   1.00    1.00    --  108.00 178.00 150.00   38
 16  \w     63.00 109.00   1.00    1.00    --  108.00 -94.00-180.00   46
 17  \w     72.00 112.00   1.00    1.00    --  108.00-111.00 -60.00   40
 18  \w     40.00 112.00   1.00    1.00    --  108.00-111.00 120.00   72
 19  \w     42.00  89.00   1.00    1.00    --  108.00 -77.00 120.00   47
 20  \w    107.00 158.00   1.00    1.00    --  108.00  61.00   0.00   51
 21  \w     39.00 122.00   1.00    1.00    --  108.00 -45.00 150.00   83
 22  \w    103.00 147.00   1.00    1.00    --  108.00 178.00 150.00   44
 23  \w     82.00 171.00   1.00    1.00    --  108.00  30.00 -30.00   89
;
_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      0.1642834000
_diffrn_orient_matrix_UB_12      0.1768710000
_diffrn_orient_matrix_UB_13      0.0295784000
_diffrn_orient_matrix_UB_21      0.1907966000
_diffrn_orient_matrix_UB_22      -0.1152545000
_diffrn_orient_matrix_UB_23      -0.0093837000
_diffrn_orient_matrix_UB_31      0.0116386000
_diffrn_orient_matrix_UB_32      0.0335934000
_diffrn_orient_matrix_UB_33      -0.0961329000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0401
_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       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4915
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         5.803
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.367
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65064
_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    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0095(10)
_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   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0551P)^2^+0.1130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1884
_reflns_number_total             2450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc03861j2.cif
_cod_data_source_block           20200636
_cod_depositor_comments
'Adding full bibliography for 7242065--7242072.cif.'
_cod_original_cell_volume        686.48(11)
_cod_database_code               7242066
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4F1
_shelx_estimated_absorpt_t_max   0.798
_shelx_estimated_absorpt_t_min   0.675
_reflns_odcompleteness_completeness 99.80
_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), C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              60520
_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 1.735
_oxdiff_exptl_absorpt_empirical_full_min 0.863