#------------------------------------------------------------------------------
#$Date: 2021-03-05 04:12:51 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262667 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/20/7242071.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7242071
loop_
_publ_author_name
'Li, Wenhao'
'Duan, Wenxue'
'Tang, Qingxuan'
'Li, Zhan-Ting'
'Yang, Guanyu'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -32.00   1.00    2.00    --  -33.50 178.00-150.00   76
  2  ω   -102.00 -15.00   1.00    2.00    --  -33.50 -57.00-180.00   87
  3  ω    -81.00  14.00   1.00    2.00    --  -33.50 112.00  -9.00   95
  4  ω   -108.00 -32.00   1.00    2.00    --  -33.50 178.00 150.00   76
  5  ω    -71.00  39.00   1.00    2.00    --  -33.50  19.00   0.00  110
  6  ω     14.00 107.00   1.00    2.00    --   36.47  37.00-180.00   93
  7  ω     -4.00  77.00   1.00    2.00    --   36.47 -99.00-180.00   81
  8  ω      8.00 106.00   1.00    2.00    --   36.47  77.00  60.00   98
  9  ω     57.00 110.00   1.00    2.00    --   36.47 178.00  30.00   53
 10  ω     38.00 110.00   1.00    2.50    --  108.00 -94.00 150.00   72
 11  ω     38.00 110.00   1.00    2.50    --  108.00 -94.00 -90.00   72
 12  ω     82.00 178.00   1.00    2.50    --  108.00  30.00 -30.00   96
 13  ω     38.00 128.00   1.00    2.50    --  108.00 -45.00 150.00   90
 14  ω     40.00 128.00   1.00    2.50    --  108.00 -61.00 -60.00   88
 15  ω    100.00 178.00   1.00    2.50    --  108.00 111.00 -60.00   78
 16  ω     96.00 133.00   1.00    2.50    --  108.00  77.00  90.00   37
 17  ω     52.00 119.00   1.00    2.50    --  108.00 -61.00-120.00   67
 18  ω     40.00 119.00   1.00    2.50    --  108.00 -45.00  30.00   79
 19  ω     63.00 107.00   1.00    2.50    --  108.00-111.00  90.00   44
 20  ω     79.00 105.00   1.00    2.50    --  108.00 -94.00 -30.00   26
 21  ω     90.00 177.00   1.00    2.50    --  108.00  30.00  60.00   87
 22  ω     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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0708P)²+0.0206P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3374(2) -0.13821(19) 0.46721(15) 0.0551(4) Uani 1 1 d . . . . .
O2 O 0.4964(2) 0.2869(2) 0.06719(14) 0.0639(5) Uani 1 1 d . . . . .
O3 O 0.3010(2) 0.59238(19) 0.16758(16) 0.0648(5) Uani 1 1 d . . . . .
H3 H 0.3673 0.5841 0.0953 0.097 Uiso 1 1 calc GR . . . .
N1 N 0.1206(3) 0.1815(3) 0.56981(19) 0.0556(5) Uani 1 1 d . . . . .
C1 C 0.2517(4) -0.3461(3) 0.6703(2) 0.0636(7) Uani 1 1 d . . . . .
H1 H 0.3235 -0.4499 0.6348 0.076 Uiso 1 1 calc R . . . .
C2 C 0.1559(4) -0.3729(4) 0.7995(3) 0.0712(7) Uani 1 1 d . . . . .
H2 H 0.1649 -0.4965 0.8525 0.085 Uiso 1 1 calc R . . . .
C3 C 0.0467(4) -0.2178(4) 0.8510(3) 0.0719(7) Uani 1 1 d . . . . .
H3A H -0.0184 -0.2381 0.9377 0.086 Uiso 1 1 calc R . . . .
C4 C 0.0332(3) -0.0343(4) 0.7755(2) 0.0656(7) Uani 1 1 d . . . . .
H4 H -0.0406 0.0689 0.8110 0.079 Uiso 1 1 calc R . . . .
C5 C 0.1307(3) -0.0030(3) 0.6450(2) 0.0532(5) Uani 1 1 d . . . . .
C6 C 0.2385(3) -0.1616(3) 0.5950(2) 0.0519(5) Uani 1 1 d . . . . .
C7 C 0.2170(3) 0.2028(3) 0.4496(2) 0.0485(5) Uani 1 1 d . . . . .
C8 C 0.3313(3) 0.0420(3) 0.3915(2) 0.0461(5) Uani 1 1 d . . . . .
C9 C 0.4282(3) 0.0615(3) 0.2665(2) 0.0470(5) Uani 1 1 d . . . . .
C10 C 0.4178(3) 0.2532(3) 0.1852(2) 0.0482(5) Uani 1 1 d . . . . .
C11 C 0.3064(3) 0.4167(3) 0.2447(2) 0.0495(5) Uani 1 1 d . . . . .
C12 C 0.2115(3) 0.3913(3) 0.3693(2) 0.0537(6) Uani 1 1 d . . . . .
H12 H 0.1418 0.4964 0.4039 0.064 Uiso 1 1 calc R . . . .
C13 C 0.5413(4) -0.1048(3) 0.2069(2) 0.0685(7) Uani 1 1 d . . . . .
H13A H 0.6239 -0.2076 0.2772 0.103 Uiso 1 1 calc GR . . . .
H13B H 0.6160 -0.0639 0.1260 0.103 Uiso 1 1 calc GR . . . .
H13C H 0.4563 -0.1490 0.1795 0.103 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C6 119.10(17) . . ?
C11 O3 H3 109.5 . . ?
C7 N1 C5 117.74(19) . . ?
C2 C1 H1 120.8 . . ?
C2 C1 C6 118.4(2) . . ?
C6 C1 H1 120.8 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 120.1(2) . . ?
N1 C5 C6 121.7(2) . . ?
C6 C5 C4 118.2(2) . . ?
O1 C6 C1 117.5(2) . . ?
O1 C6 C5 120.39(18) . . ?
C1 C6 C5 122.1(2) . . ?
N1 C7 C8 122.94(18) . . ?
N1 C7 C12 119.4(2) . . ?
C12 C7 C8 117.65(19) . . ?
O1 C8 C7 118.08(18) . . ?
C9 C8 O1 118.06(18) . . ?
C9 C8 C7 123.85(18) . . ?
C8 C9 C10 117.85(19) . . ?
C8 C9 C13 123.09(18) . . ?
C10 C9 C13 119.05(18) . . ?
O2 C10 C9 122.75(19) . . ?
O2 C10 C11 118.44(18) . . ?
C9 C10 C11 118.81(18) . . ?
O3 C11 C10 117.46(18) . . ?
C12 C11 O3 121.03(19) . . ?
C12 C11 C10 121.50(18) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.378(2) . ?
O1 C8 1.367(2) . ?
O2 C10 1.237(2) . ?
O3 H3 0.8200 . ?
O3 C11 1.342(2) . ?
N1 C5 1.386(3) . ?
N1 C7 1.307(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C6 1.380(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.373(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.399(3) . ?
C5 C6 1.394(3) . ?
C7 C8 1.463(3) . ?
C7 C12 1.435(3) . ?
C8 C9 1.346(3) . ?
C9 C10 1.448(3) . ?
C9 C13 1.502(3) . ?
C10 C11 1.483(3) . ?
C11 C12 1.339(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C8 C9 C10 178.62(16) . . . . ?
O1 C8 C9 C13 0.2(3) . . . . ?
O2 C10 C11 O3 -1.5(3) . . . . ?
O2 C10 C11 C12 177.3(2) . . . . ?
O3 C11 C12 C7 179.27(19) . . . . ?
N1 C5 C6 O1 -0.7(3) . . . . ?
N1 C5 C6 C1 178.9(2) . . . . ?
N1 C7 C8 O1 -0.3(3) . . . . ?
N1 C7 C8 C9 178.5(2) . . . . ?
N1 C7 C12 C11 -178.73(19) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C1 C6 O1 179.10(19) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 N1 -178.7(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 O1 -179.88(18) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C5 N1 C7 C8 0.8(3) . . . . ?
C5 N1 C7 C12 -179.47(18) . . . . ?
C6 O1 C8 C7 -0.8(3) . . . . ?
C6 O1 C8 C9 -179.63(17) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C7 N1 C5 C4 178.77(19) . . . . ?
C7 N1 C5 C6 -0.3(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C8 C9 C13 -178.58(19) . . . . ?
C8 O1 C6 C1 -178.36(18) . . . . ?
C8 O1 C6 C5 1.3(3) . . . . ?
C8 C7 C12 C11 1.0(3) . . . . ?
C8 C9 C10 O2 -177.51(19) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
C9 C10 C11 O3 179.33(18) . . . . ?
C9 C10 C11 C12 -1.9(3) . . . . ?
C10 C11 C12 C7 0.5(3) . . . . ?
C12 C7 C8 O1 -179.97(17) . . . . ?
C12 C7 C8 C9 -1.2(3) . . . . ?
C13 C9 C10 O2 1.0(3) . . . . ?
C13 C9 C10 C11 -179.8(2) . . . . ?
