#------------------------------------------------------------------------------
#$Date: 2021-03-05 04:12:51 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262667 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/20/7242072.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_7242072
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         'C14 H11 N O5'
_chemical_formula_sum            'C14 H11 N O5'
_chemical_formula_weight         273.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-13 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.744(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4314(8)
_cell_length_b                   4.4645(3)
_cell_length_c                   18.5538(11)
_cell_measurement_reflns_used    875
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1820
_cell_measurement_theta_min      6.0980
_cell_volume                     1195.30(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    '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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   0.50   12.50    --  -33.50 -57.00  90.00  174
  2  ω   -104.00 -11.00   0.50   12.50    --  -33.50 -37.00 -30.00  186
  3  ω     14.00 107.00   0.50   12.50    --   36.47  37.00 -60.00  186
  4  ω     14.00 107.00   0.50   12.50    --   36.47  37.00 -30.00  186
  5  ω     41.00 109.00   0.50   12.50    --   36.47  19.00-180.00  136
  6  ω     84.00 110.00   0.50   12.50    --   36.47 178.00 -60.00   52
  7  ω     20.00  60.00   0.50   12.50    --   36.47  57.00  60.00   80
  8  ω     80.00 105.00   0.50   12.50    --   36.47  57.00  60.00   50
  9  ω     82.00 108.00   0.50   12.50    --   36.47 178.00 -90.00   52
 10  ω     72.00 164.00   0.50   17.50    --  108.00  15.00 150.00  184
 11  ω     40.00 107.00   0.50   17.50    --  108.00 -94.00-180.00  134
 12  ω     41.00 107.00   0.50   17.50    --  108.00 -45.00 150.00  132
 13  ω    146.00 175.00   0.50   17.50    --  108.00 111.00  60.00   58
 14  ω     39.00  64.00   0.50   17.50    --  108.00-111.00 150.00   50
 15  ω    149.00 174.00   0.50   17.50    --  108.00 111.00 120.00   50
 16  ω     38.00 134.00   0.50   17.50    --  108.00 -30.00 -60.00  192
 17  ω    149.00 174.00   0.50   17.50    --  108.00  61.00 -60.00   50
 18  ω    109.00 135.00   0.50   17.50    --  108.00  61.00 -60.00   52
;
_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      -0.0000448000
_diffrn_orient_matrix_UB_12      -0.1035427000
_diffrn_orient_matrix_UB_13      0.0792158000
_diffrn_orient_matrix_UB_21      0.1065059000
_diffrn_orient_matrix_UB_22      0.0219568000
_diffrn_orient_matrix_UB_23      0.0027481000
_diffrn_orient_matrix_UB_31      -0.0071057000
_diffrn_orient_matrix_UB_32      0.3283983000
_diffrn_orient_matrix_UB_33      0.0248308000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4371
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         3.856
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.990
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90567
_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    1.518
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0493
_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)+(0.0691P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1388
_reflns_number_total             2131
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0gc03861j2.cif
_cod_data_source_block           202007123
_cod_depositor_comments
'Adding full bibliography for 7242065--7242072.cif.'
_cod_original_cell_volume        1195.28(12)
_cod_database_code               7242072
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C14H15N2O1
_chemical_oxdiff_usercomment     r
_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   0.961
_shelx_estimated_absorpt_t_min   0.827
_reflns_odcompleteness_completeness 99.43
_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:
 C4(H4), C9(H9), C11(H11), 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)
;
_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 1.166
_oxdiff_exptl_absorpt_empirical_full_min 0.853
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C 0.44860(17) 0.3321(6) 0.24922(12) 0.0455(6) Uani 1 1 d . . . . .
C2 C 0.37752(17) 0.5450(6) 0.26834(13) 0.0455(6) Uani 1 1 d . . . . .
C3 C 0.37551(16) 0.6425(6) 0.34480(13) 0.0439(6) Uani 1 1 d . . . . .
C4 C 0.43447(16) 0.5311(6) 0.39500(12) 0.0431(6) Uani 1 1 d . . . . .
H4 H 0.4313 0.5975 0.4424 0.052 Uiso 1 1 calc R . . . .
C5 C 0.50181(16) 0.3117(5) 0.37569(12) 0.0412(6) Uani 1 1 d . . . . .
C6 C 0.50559(16) 0.2169(5) 0.29988(12) 0.0418(6) Uani 1 1 d . . . . .
C7 C 0.62893(17) -0.1026(5) 0.33268(12) 0.0435(6) Uani 1 1 d . . . . .
C8 C 0.62400(16) -0.0047(6) 0.40364(12) 0.0416(6) Uani 1 1 d . . . . .
C9 C 0.68732(17) -0.1172(6) 0.45488(13) 0.0473(6) Uani 1 1 d . . . . .
H9 H 0.6851 -0.0529 0.5025 0.057 Uiso 1 1 calc R . . . .
C10 C 0.75265(17) -0.3233(6) 0.43423(14) 0.0492(6) Uani 1 1 d . . . . .
C11 C 0.75479(18) -0.4241(6) 0.36237(14) 0.0522(7) Uani 1 1 d . . . . .
H11 H 0.7983 -0.5668 0.3491 0.063 Uiso 1 1 calc R . . . .
C12 C 0.69363(17) -0.3146(6) 0.31182(14) 0.0483(6) Uani 1 1 d . . . . .
H12 H 0.6954 -0.3811 0.2644 0.058 Uiso 1 1 calc R . . . .
C13 C 0.5139(2) 0.4253(8) 0.13672(15) 0.0731(9) Uani 1 1 d . . . . .
H13A H 0.5106 0.3641 0.0871 0.110 Uiso 1 1 calc GR . . . .
H13B H 0.5763 0.4038 0.1544 0.110 Uiso 1 1 calc GR . . . .
H13C H 0.4952 0.6309 0.1406 0.110 Uiso 1 1 calc GR . . . .
C14 C 0.8239(2) -0.3341(7) 0.55045(15) 0.0719(9) Uani 1 1 d . . . . .
H14A H 0.8360 -0.1227 0.5493 0.108 Uiso 1 1 calc GR . . . .
H14B H 0.8731 -0.4338 0.5761 0.108 Uiso 1 1 calc GR . . . .
H14C H 0.7663 -0.3701 0.5743 0.108 Uiso 1 1 calc GR . . . .
N1 N 0.55866(13) 0.2053(5) 0.42491(10) 0.0422(5) Uani 1 1 d . . . . .
O1 O 0.45363(13) 0.2422(5) 0.17836(9) 0.0608(6) Uani 1 1 d . . . . .
O2 O 0.32023(12) 0.6488(4) 0.22523(9) 0.0574(5) Uani 1 1 d . . . . .
O3 O 0.31146(12) 0.8464(4) 0.36208(9) 0.0548(5) Uani 1 1 d . . . . .
H3 H 0.2812 0.8916 0.3260 0.082 Uiso 1 1 calc GR . . . .
O4 O 0.56977(11) 0.0098(4) 0.28017(8) 0.0483(5) Uani 1 1 d . . . . .
O5 O 0.81826(13) -0.4469(5) 0.47829(10) 0.0651(6) Uani 1 1 d . . . . .
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
C6 C1 C2 120.7(2) . . ?
C6 C1 O1 121.1(2) . . ?
O1 C1 C2 118.2(2) . . ?
C1 C2 C3 116.7(2) . . ?
O2 C2 C1 124.0(2) . . ?
O2 C2 C3 119.2(2) . . ?
C4 C3 C2 122.1(2) . . ?
O3 C3 C2 116.8(2) . . ?
O3 C3 C4 121.1(2) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 118.1(2) . . ?
N1 C5 C4 119.7(2) . . ?
N1 C5 C6 122.1(2) . . ?
C1 C6 C5 121.9(2) . . ?
C1 C6 O4 119.0(2) . . ?
O4 C6 C5 119.1(2) . . ?
C12 C7 C8 121.4(2) . . ?
O4 C7 C8 121.0(2) . . ?
O4 C7 C12 117.6(2) . . ?
C7 C8 C9 119.2(2) . . ?
C7 C8 N1 121.6(2) . . ?
N1 C8 C9 119.2(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.1(2) . . ?
O5 C10 C9 125.4(2) . . ?
O5 C10 C11 114.6(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.6 . . ?
C11 C12 C7 118.8(2) . . ?
C11 C12 H12 120.6 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
C5 N1 C8 117.9(2) . . ?
C1 O1 C13 112.9(2) . . ?
C3 O3 H3 109.5 . . ?
C6 O4 C7 118.26(18) . . ?
C10 O5 C14 116.7(2) . . ?
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
C1 C2 1.446(3) . ?
C1 C6 1.343(3) . ?
C1 O1 1.377(3) . ?
C2 C3 1.485(3) . ?
C2 O2 1.233(3) . ?
C3 C4 1.348(3) . ?
C3 O3 1.339(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.429(3) . ?
C5 C6 1.471(3) . ?
C5 N1 1.309(3) . ?
C6 O4 1.362(3) . ?
C7 C8 1.390(3) . ?
C7 C12 1.388(3) . ?
C7 O4 1.381(3) . ?
C8 C9 1.403(3) . ?
C8 N1 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(3) . ?
C10 C11 1.408(4) . ?
C10 O5 1.360(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 O1 1.428(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 O5 1.432(3) . ?
O3 H3 0.8200 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.82 2.08 2.825(2) 150.8 2
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
C1 C2 C3 C4 -2.4(4) . . . . ?
C1 C2 C3 O3 178.1(2) . . . . ?
C1 C6 O4 C7 178.9(2) . . . . ?
C2 C1 C6 C5 -3.2(4) . . . . ?
C2 C1 C6 O4 177.9(2) . . . . ?
C2 C1 O1 C13 90.8(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 N1 -180.0(2) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 O4 179.5(2) . . . . ?
C4 C5 N1 C8 -179.1(2) . . . . ?
C5 C6 O4 C7 -0.1(3) . . . . ?
C6 C1 C2 C3 4.0(3) . . . . ?
C6 C1 C2 O2 -176.5(2) . . . . ?
C6 C1 O1 C13 -91.8(3) . . . . ?
C6 C5 N1 C8 -0.2(3) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C7 C8 N1 C5 -0.6(3) . . . . ?
C8 C7 C12 C11 -1.3(4) . . . . ?
C8 C7 O4 C6 -0.8(3) . . . . ?
C8 C9 C10 C11 -1.1(4) . . . . ?
C8 C9 C10 O5 179.3(2) . . . . ?
C9 C8 N1 C5 178.5(2) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
C9 C10 O5 C14 -5.3(4) . . . . ?
C10 C11 C12 C7 -0.3(4) . . . . ?
C11 C10 O5 C14 175.1(2) . . . . ?
C12 C7 C8 C9 1.6(4) . . . . ?
C12 C7 C8 N1 -179.3(2) . . . . ?
C12 C7 O4 C6 179.7(2) . . . . ?
N1 C5 C6 C1 -178.4(2) . . . . ?
N1 C5 C6 O4 0.5(3) . . . . ?
N1 C8 C9 C10 -179.5(2) . . . . ?
O1 C1 C2 C3 -178.6(2) . . . . ?
O1 C1 C2 O2 0.9(4) . . . . ?
O1 C1 C6 C5 179.5(2) . . . . ?
O1 C1 C6 O4 0.6(4) . . . . ?
O2 C2 C3 C4 178.1(2) . . . . ?
O2 C2 C3 O3 -1.4(3) . . . . ?
O3 C3 C4 C5 179.4(2) . . . . ?
O4 C7 C8 C9 -178.0(2) . . . . ?
O4 C7 C8 N1 1.1(4) . . . . ?
O4 C7 C12 C11 178.3(2) . . . . ?
O5 C10 C11 C12 -178.9(2) . . . . ?
