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_7242070
_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 H8 Br N O3'
_chemical_formula_sum            'C13 H8 Br N O3'
_chemical_formula_weight         306.11
_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     direct
_audit_creation_date             2020-04-28
_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                 96.343(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.70525(16)
_cell_length_b                   13.1424(4)
_cell_length_c                   18.3356(5)
_cell_measurement_reflns_used    1656
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3190
_cell_measurement_theta_min      4.1330
_cell_volume                     1126.90(6)
_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    -56.00  37.00   1.00    2.50    --  -33.50  37.00 -30.00   93
  2  \w   -102.00 -15.00   1.00    2.50    --  -33.50 -57.00-180.00   87
  3  \w     18.00 105.00   1.00    2.50    --   36.47  57.00  30.00   87
  4  \w    -33.00  65.00   1.00    2.50    --   36.47 -77.00  60.00   98
  5  \w     66.00 106.00   1.00    2.50    --   36.47 178.00 -90.00   40
  6  \w     69.00  94.00   1.00    2.50    --   36.47-141.00 137.00   25
  7  \w    101.00 127.00   1.00    8.00    --  108.00 111.00-150.00   26
  8  \w     43.00 110.00   1.00    8.00    --  108.00-111.00-150.00   67
  9  \w    144.00 178.00   1.00    8.00    --  108.00 124.00 116.00   34
 10  \w     37.00 131.00   1.00    8.00    --  108.00 -30.00  30.00   94
 11  \w    100.00 126.00   1.00    8.00    --  108.00 124.00 116.00   26
 12  \w     39.00 127.00   1.00    8.00    --  108.00 -45.00 -60.00   88
 13  \w     62.00 109.00   1.00    8.00    --  108.00 -94.00-120.00   47
 14  \w     64.00 159.00   1.00    8.00    --  108.00  15.00  60.00   95
;
_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      0.0604649000
_diffrn_orient_matrix_UB_12      -0.0253304000
_diffrn_orient_matrix_UB_13      0.0822715000
_diffrn_orient_matrix_UB_21      0.0245428000
_diffrn_orient_matrix_UB_22      -0.1136960000
_diffrn_orient_matrix_UB_23      -0.0188677000
_diffrn_orient_matrix_UB_31      0.3228663000
_diffrn_orient_matrix_UB_32      0.0134251000
_diffrn_orient_matrix_UB_33      -0.0044365000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4063
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.061
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         4.147
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.990
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80972
_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    1.804
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0817P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1420
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1670
_reflns_number_total             2011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc03861j2.cif
_cod_data_source_block           20200427
_cod_depositor_comments
'Adding full bibliography for 7242065--7242072.cif.'
_cod_database_code               7242070
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O4Cl1Br1
_shelx_estimated_absorpt_t_max   0.865
_shelx_estimated_absorpt_t_min   0.435
_reflns_odcompleteness_completeness 99.67
_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), C3(H3), C4(H4), C9(H9)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              26820
_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 1.596
_oxdiff_exptl_absorpt_empirical_full_min 0.795