# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tx2667
_database_code_depnum_ccdc_archive 'CCDC 2050910'
loop_
_audit_author_name
_audit_author_address
'wang man'
;University
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-09-15 downloaded from the CCDC.
;
_audit_creation_date             2020-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N O3'
_chemical_formula_sum            'C19 H15 N O3'
_chemical_formula_weight         305.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.18780(10)
_cell_length_b                   10.5485(2)
_cell_length_c                   18.4881(3)
_cell_angle_alpha                74.8690(10)
_cell_angle_beta                 88.4730(10)
_cell_angle_gamma                89.1010(10)
_cell_volume                     1540.83(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14140
_cell_measurement_temperature    170.00(12)
_cell_measurement_theta_max      75.1720
_cell_measurement_theta_min      4.3210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20582
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.362
_diffrn_reflns_theta_min         2.476
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -43.00   0.50    0.05    --  -47.20 -40.00  75.00  138
  2  ω    -37.00   2.00   0.50    0.05    --  -47.20  40.00-131.00   78
  3  ω     48.00 106.00   0.50    0.05    --   47.20  40.00-131.00  116
  4  ω   -120.00 -87.00   0.50    0.05    --  -99.00 -40.00  75.00   66
  5  ω   -166.00-125.00   0.50    0.05    --  -99.00 -40.00  75.00   82
  6  ω     96.00 143.00   0.50    0.05    --  103.25  40.00-131.00   94
  7  ω   -108.00 -78.00   0.50    0.05    --  -47.20-125.00 -30.00   60
  8  ω   -114.00 -75.00   0.50    0.05    --  -47.20-125.00  30.00   78
  9  ω    -19.00  16.00   0.50    0.05    --  -47.20  38.00   0.00   70
 10  ω    -11.00  16.00   0.50    0.05    --   47.20 -77.00-120.00   54
 11  ω     30.00  67.00   0.50    0.05    --   47.20 -77.00-120.00   74
 12  ω    -23.00  44.00   0.50    0.05    --   47.20 -40.00  75.00  134
 13  ω    -27.00  30.00   0.50    0.05    --   47.20 -19.00 -60.00  114
 14  ω   -112.00 -50.00   0.50    0.05    --  -99.00 125.00-150.00  124
 15  ω    -66.00 -32.00   0.50    0.05    --  -99.00  61.00  90.00   68
 16  ω   -108.00 -74.00   0.50    0.05    --  -99.00 110.00 -15.45   68
 17  ω   -166.00 -87.00   0.50    0.05    --  -99.00 -45.00 150.00  158
 18  ω   -112.00 -31.00   0.50    0.05    --  -99.00 125.00 150.00  162
 19  ω    -58.00 -32.00   0.50    0.05    --  -99.00  77.00 -30.00   52
 20  ω    -92.00 -67.00   0.50    0.05    --  -99.00  77.00 -30.00   50
 21  ω   -109.00 -79.00   0.50    0.05    --  -99.00 115.00-157.50   60
 22  ω   -112.00 -27.00   0.50    0.05    --  -99.00 125.00  60.00  170
 23  ω   -100.00 -35.00   0.50    0.05    --  -99.00  77.00  30.00  130
 24  ω    -82.00 -45.00   0.50    0.05    --  -99.00 125.00  90.00   74
 25  ω   -111.00 -32.00   0.50    0.05    --  -99.00 125.00   0.00  158
 26  ω     33.00  58.00   0.50    0.05    --  103.25-125.00 120.00   50
 27  ω     46.00 106.00   0.50    0.05    --  103.25 -94.00-120.00  120
 28  ω     36.00 109.00   0.50    0.05    --  103.25 -77.00-180.00  146
 29  ω     31.00  56.00   0.50    0.05    --  103.25 -61.00 120.00   50
 30  ω     35.00  74.00   0.50    0.05    --  103.25 -61.00  60.00   78
 31  ω     36.00  79.00   0.50    0.05    --  103.25 -94.00 150.00   86
 32  ω     43.00  94.00   0.50    0.05    --  103.25 -77.00   0.00  102
 33  ω     51.00 105.00   0.50    0.05    --  103.25 -94.00 -60.00  108
 34  ω     32.00  75.00   0.50    0.05    --  103.25 -61.00-120.00   86
 35  ω     91.00 169.00   0.50    0.05    --  103.25  15.00 -90.00  156
 36  ω    104.00 169.00   0.50    0.05    --  103.25  30.00   0.00  130
 37  ω    138.00 164.00   0.50    0.05    --  103.25  45.00 -30.00   52
 38  ω     86.00 111.00   0.50    0.05    --  103.25-125.00 120.00   50
 39  ω     91.00 125.00   0.50    0.05    --  103.25  45.00 -30.00   68
 40  ω     99.00 159.00   0.50    0.05    --  103.25  15.00 -30.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1254056000
_diffrn_orient_matrix_UB_12      -0.0720132000
_diffrn_orient_matrix_UB_13      -0.0390030000
_diffrn_orient_matrix_UB_21      -0.1071429000
_diffrn_orient_matrix_UB_22      -0.1235955000
_diffrn_orient_matrix_UB_23      0.0206945000
_diffrn_orient_matrix_UB_31      -0.0906830000
_diffrn_orient_matrix_UB_32      0.0492866000
_diffrn_orient_matrix_UB_33      -0.0742002000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5599
_reflns_number_total             6116
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0753P)²+0.5319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1285
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), N1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A),
  C8A(H8A), C10A(H10A), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A),
 C19A(H19A)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C13A(H13D,H13E,H13F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.19039(13) 0.49212(9) 0.47293(5) 0.0314(2) Uani 1 1 d . . . . .
O2 O 0.14299(16) 0.60771(12) 0.58788(6) 0.0443(3) Uani 1 1 d . . . . .
O3 O 0.01554(14) 0.77248(10) 0.50662(6) 0.0378(3) Uani 1 1 d . . . . .
N1 N 0.22478(14) 0.90902(12) 0.13300(6) 0.0282(3) Uani 1 1 d . . . . .
H1 H 0.266131 0.932665 0.088308 0.034 Uiso 1 1 calc R . . . .
C1 C 0.12148(16) 0.98460(13) 0.16486(8) 0.0268(3) Uani 1 1 d . . . . .
C2 C 0.05510(19) 1.10810(14) 0.13212(9) 0.0348(3) Uani 1 1 d . . . . .
H2 H 0.082028 1.153284 0.083077 0.042 Uiso 1 1 calc R . . . .
C3 C -0.0516(2) 1.16011(15) 0.17535(10) 0.0399(4) Uani 1 1 d . . . . .
H3 H -0.097864 1.242473 0.155254 0.048 Uiso 1 1 calc R . . . .
C4 C -0.09244(19) 1.09193(15) 0.24903(9) 0.0360(3) Uani 1 1 d . . . . .
H4 H -0.165015 1.130008 0.276928 0.043 Uiso 1 1 calc R . . . .
C5 C -0.02702(17) 0.96889(14) 0.28130(8) 0.0287(3) Uani 1 1 d . . . . .
H5 H -0.055833 0.924326 0.330228 0.034 Uiso 1 1 calc R . . . .
C6 C 0.08334(16) 0.91253(13) 0.23907(7) 0.0239(3) Uani 1 1 d . . . . .
C7 C 0.16937(15) 0.78732(13) 0.24997(7) 0.0233(3) Uani 1 1 d . . . . .
C8 C 0.25113(16) 0.79250(13) 0.18250(7) 0.0253(3) Uani 1 1 d . . . . .
H8 H 0.315142 0.724866 0.172871 0.030 Uiso 1 1 calc R . . . .
C9 C 0.18676(15) 0.68079(13) 0.31677(7) 0.0229(3) Uani 1 1 d . . . . .
C10 C 0.14942(17) 0.70180(13) 0.38524(7) 0.0258(3) Uani 1 1 d . . . . .
H10 H 0.117835 0.786985 0.384985 0.031 Uiso 1 1 calc R . . . .
C11 C 0.15278(16) 0.60897(13) 0.45758(7) 0.0252(3) Uani 1 1 d . . . . .
C12 C 0.10427(18) 0.66252(14) 0.52524(7) 0.0294(3) Uani 1 1 d . . . . .
C13 C -0.0449(3) 0.8203(2) 0.56853(11) 0.0640(6) Uani 1 1 d . . . . .
H13A H -0.112520 0.896516 0.550051 0.096 Uiso 1 1 calc GR . . . .
H13B H 0.045461 0.843199 0.594509 0.096 Uiso 1 1 calc GR . . . .
H13C H -0.108014 0.753198 0.602291 0.096 Uiso 1 1 calc GR . . . .
C14 C 0.25141(16) 0.55436(13) 0.30570(7) 0.0244(3) Uani 1 1 d . . . . .
C15 C 0.17447(19) 0.49433(14) 0.25697(8) 0.0320(3) Uani 1 1 d . . . . .
H15 H 0.079817 0.531385 0.233249 0.038 Uiso 1 1 calc R . . . .
C16 C 0.2385(2) 0.37976(16) 0.24379(9) 0.0417(4) Uani 1 1 d . . . . .
H16 H 0.184737 0.339008 0.212403 0.050 Uiso 1 1 calc R . . . .
C17 C 0.3817(2) 0.32567(15) 0.27697(9) 0.0434(4) Uani 1 1 d . . . . .
H17 H 0.425692 0.250043 0.266970 0.052 Uiso 1 1 calc R . . . .
C18 C 0.4594(2) 0.38481(15) 0.32529(9) 0.0388(4) Uani 1 1 d . . . . .
H18 H 0.555789 0.348850 0.347719 0.047 Uiso 1 1 calc R . . . .
C19 C 0.39367(17) 0.49699(14) 0.34010(8) 0.0282(3) Uani 1 1 d . . . . .
H19 H 0.445014 0.534821 0.373495 0.034 Uiso 1 1 calc R . . . .
O1A O 0.31077(13) 0.04733(10) 0.98201(5) 0.0311(2) Uani 1 1 d . . . . .
O2A O 0.36203(15) -0.21714(10) 1.01942(6) 0.0407(3) Uani 1 1 d . . . . .
O3A O 0.50927(13) -0.18860(9) 0.91249(5) 0.0315(2) Uani 1 1 d . . . . .
N1A N 0.27783(14) 0.33541(12) 0.61662(6) 0.0285(3) Uani 1 1 d . . . . .
H1A H 0.235576 0.393202 0.580022 0.034 Uiso 1 1 calc R . . . .
C1A C 0.38341(17) 0.23605(14) 0.60933(7) 0.0268(3) Uani 1 1 d . . . . .
C2A C 0.44954(19) 0.21200(16) 0.54393(8) 0.0344(3) Uani 1 1 d . . . . .
H2A H 0.421770 0.263727 0.496883 0.041 Uiso 1 1 calc R . . . .
C3A C 0.5577(2) 0.10846(16) 0.55196(9) 0.0384(4) Uani 1 1 d . . . . .
H3A H 0.604195 0.089447 0.509524 0.046 Uiso 1 1 calc R . . . .
C4A C 0.5988(2) 0.03112(15) 0.62312(9) 0.0358(3) Uani 1 1 d . . . . .
H4A H 0.671843 -0.038592 0.626876 0.043 Uiso 1 1 calc R . . . .
C5A C 0.53350(17) 0.05590(13) 0.68791(8) 0.0285(3) Uani 1 1 d . . . . .
H5A H 0.563024 0.004170 0.734690 0.034 Uiso 1 1 calc R . . . .
C6A C 0.42216(16) 0.16018(13) 0.68193(7) 0.0235(3) Uani 1 1 d . . . . .
C7A C 0.33494(15) 0.22080(12) 0.73400(7) 0.0227(3) Uani 1 1 d . . . . .
C8A C 0.25108(16) 0.32812(13) 0.68955(7) 0.0259(3) Uani 1 1 d . . . . .
H8A H 0.185924 0.386336 0.707857 0.031 Uiso 1 1 calc R . . . .
C9A C 0.31740(15) 0.17899(12) 0.81451(7) 0.0222(3) Uani 1 1 d . . . . .
C10A C 0.35850(16) 0.05316(13) 0.85252(7) 0.0246(3) Uani 1 1 d . . . . .
H10A H 0.393971 -0.001859 0.823224 0.030 Uiso 1 1 calc R . . . .
C11A C 0.35344(16) -0.00394(13) 0.93198(7) 0.0245(3) Uani 1 1 d . . . . .
C12A C 0.40737(17) -0.14916(13) 0.95965(7) 0.0274(3) Uani 1 1 d . . . . .
C13A C 0.5816(2) -0.31697(15) 0.94260(9) 0.0408(4) Uani 1 1 d . . . . .
H13D H 0.652693 -0.338539 0.905327 0.061 Uiso 1 1 calc GR . . . .
H13E H 0.496871 -0.381244 0.956520 0.061 Uiso 1 1 calc GR . . . .
H13F H 0.643313 -0.316306 0.985934 0.061 Uiso 1 1 calc GR . . . .
C14A C 0.24892(16) 0.27864(13) 0.85139(7) 0.0231(3) Uani 1 1 d . . . . .
C15A C 0.32048(17) 0.40236(13) 0.83757(8) 0.0281(3) Uani 1 1 d . . . . .
H15A H 0.414961 0.420286 0.807792 0.034 Uiso 1 1 calc R . . . .
C16A C 0.25186(19) 0.49860(14) 0.86787(8) 0.0334(3) Uani 1 1 d . . . . .
H16A H 0.301327 0.580178 0.858866 0.040 Uiso 1 1 calc R . . . .
C17A C 0.1099(2) 0.47373(15) 0.91150(8) 0.0343(3) Uani 1 1 d . . . . .
H17A H 0.063520 0.538637 0.931449 0.041 Uiso 1 1 calc R . . . .
C18A C 0.03723(18) 0.35157(15) 0.92528(8) 0.0311(3) Uani 1 1 d . . . . .
H18A H -0.058498 0.334722 0.954244 0.037 Uiso 1 1 calc R . . . .
C19A C 0.10689(16) 0.25464(13) 0.89603(7) 0.0256(3) Uani 1 1 d . . . . .
H19A H 0.058409 0.172528 0.906265 0.031 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C11 1.2268(16) . ?
O2 C12 1.2001(18) . ?
O3 C12 1.3304(17) . ?
O3 C13 1.4400(19) . ?
N1 C1 1.3768(19) . ?
N1 C8 1.3452(17) . ?
C1 C2 1.3938(19) . ?
C1 C6 1.4135(18) . ?
C2 C3 1.371(2) . ?
C3 C4 1.399(2) . ?
C4 C5 1.385(2) . ?
C5 C6 1.4027(19) . ?
C6 C7 1.4562(18) . ?
C7 C8 1.3887(18) . ?
C7 C9 1.4450(17) . ?
C9 C10 1.3672(18) . ?
C9 C14 1.4883(18) . ?
C10 C11 1.4372(17) . ?
C11 C12 1.5417(19) . ?
C14 C15 1.396(2) . ?
C14 C19 1.3942(19) . ?
C15 C16 1.386(2) . ?
C16 C17 1.382(3) . ?
C17 C18 1.388(3) . ?
C18 C19 1.381(2) . ?
O1A C11A 1.2280(16) . ?
O2A C12A 1.2025(17) . ?
O3A C12A 1.3301(17) . ?
O3A C13A 1.4468(17) . ?
N1A C1A 1.3795(19) . ?
N1A C8A 1.3427(18) . ?
C1A C2A 1.393(2) . ?
C1A C6A 1.4131(18) . ?
C2A C3A 1.375(2) . ?
C3A C4A 1.402(2) . ?
C4A C5A 1.383(2) . ?
C5A C6A 1.4013(19) . ?
C6A C7A 1.4546(18) . ?
C7A C8A 1.3959(18) . ?
C7A C9A 1.4418(17) . ?
C9A C10A 1.3713(18) . ?
C9A C14A 1.4898(18) . ?
C10A C11A 1.4347(17) . ?
C11A C12A 1.5444(18) . ?
C14A C15A 1.3977(19) . ?
C14A C19A 1.3952(19) . ?
C15A C16A 1.386(2) . ?
C16A C17A 1.386(2) . ?
C17A C18A 1.387(2) . ?
C18A C19A 1.385(2) . ?

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
C12 O3 C13 115.34(12) . . ?
C8 N1 C1 109.56(11) . . ?
N1 C1 C2 128.60(13) . . ?
N1 C1 C6 108.12(11) . . ?
C2 C1 C6 123.21(14) . . ?
C3 C2 C1 117.11(14) . . ?
C2 C3 C4 121.41(14) . . ?
C5 C4 C3 121.38(15) . . ?
C4 C5 C6 118.98(13) . . ?
C1 C6 C7 106.07(11) . . ?
C5 C6 C1 117.90(12) . . ?
C5 C6 C7 135.91(12) . . ?
C8 C7 C6 105.72(11) . . ?
C8 C7 C9 123.84(12) . . ?
C9 C7 C6 130.17(12) . . ?
N1 C8 C7 110.51(12) . . ?
C7 C9 C14 116.39(11) . . ?
C10 C9 C7 119.46(12) . . ?
C10 C9 C14 124.12(12) . . ?
C9 C10 C11 128.25(13) . . ?
O1 C11 C10 128.52(13) . . ?
O1 C11 C12 115.25(11) . . ?
C10 C11 C12 116.23(12) . . ?
O2 C12 O3 124.74(13) . . ?
O2 C12 C11 122.09(13) . . ?
O3 C12 C11 113.17(11) . . ?
C15 C14 C9 120.07(12) . . ?
C19 C14 C9 121.29(12) . . ?
C19 C14 C15 118.55(13) . . ?
C16 C15 C14 120.32(14) . . ?
C17 C16 C15 120.45(15) . . ?
C16 C17 C18 119.65(14) . . ?
C19 C18 C17 120.05(15) . . ?
C18 C19 C14 120.93(14) . . ?
C12A O3A C13A 114.47(11) . . ?
C8A N1A C1A 109.63(11) . . ?
N1A C1A C2A 128.43(13) . . ?
N1A C1A C6A 108.14(12) . . ?
C2A C1A C6A 123.39(13) . . ?
C3A C2A C1A 117.10(14) . . ?
C2A C3A C4A 121.02(14) . . ?
C5A C4A C3A 121.64(14) . . ?
C4A C5A C6A 118.96(13) . . ?
C1A C6A C7A 106.14(11) . . ?
C5A C6A C1A 117.88(12) . . ?
C5A C6A C7A 135.87(12) . . ?
C8A C7A C6A 105.68(11) . . ?
C8A C7A C9A 123.52(12) . . ?
C9A C7A C6A 130.52(12) . . ?
N1A C8A C7A 110.38(12) . . ?
C7A C9A C14A 115.91(11) . . ?
C10A C9A C7A 120.30(12) . . ?
C10A C9A C14A 123.77(11) . . ?
C9A C10A C11A 127.89(12) . . ?
O1A C11A C10A 128.55(12) . . ?
O1A C11A C12A 114.58(11) . . ?
C10A C11A C12A 116.87(12) . . ?
O2A C12A O3A 124.48(13) . . ?
O2A C12A C11A 121.64(13) . . ?
O3A C12A C11A 113.86(11) . . ?
C15A C14A C9A 120.09(12) . . ?
C19A C14A C9A 121.29(12) . . ?
C19A C14A C15A 118.48(12) . . ?
C16A C15A C14A 120.59(13) . . ?
C17A C16A C15A 120.28(14) . . ?
C16A C17A C18A 119.67(13) . . ?
C19A C18A C17A 120.16(13) . . ?
C18A C19A C14A 120.82(13) . . ?

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
_geom_hbond_publ_flag
N1 H1 O1A 0.86 2.05 2.8667(14) 158.8 1_564 yes
N1 H1 O2A 0.86 2.39 2.9545(17) 124.0 1_564 yes
N1A H1A O1 0.86 2.02 2.8414(14) 158.6 . yes
N1A H1A O2 0.86 2.41 2.9811(17) 124.0 . yes

_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 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.714
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tx2525
_database_code_depnum_ccdc_archive 'CCDC 2040081'
loop_
_audit_author_name
_audit_author_address
wangman
;qingdao university of science and technology
China
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2021-09-15 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H13 N O3'
_chemical_formula_sum            'C19 H13 N O3'
_chemical_formula_weight         303.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5812(5)
_cell_length_b                   9.4110(6)
_cell_length_c                   10.4027(6)
_cell_angle_alpha                70.079(5)
_cell_angle_beta                 86.828(5)
_cell_angle_gamma                67.570(6)
_cell_volume                     727.38(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7442
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      75.1680
_cell_measurement_theta_min      5.5910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8335
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.371
_diffrn_reflns_theta_min         5.598
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -33.00   0.50    0.05    --  -47.20 -51.00-159.00  174
  2  ω    -47.00  23.00   0.50    0.05    --  -47.20  51.00 -13.00  140
  3  ω    -21.00  43.00   0.50    0.05    --   47.20 -51.00-159.00  128
  4  ω     37.00 115.00   0.50    0.05    --   47.20  51.00 -13.00  156
  5  ω   -165.00-107.00   0.50    0.05    --  -99.00 -51.00-159.00  116
  6  ω    -53.00 -26.00   0.50    0.05    --  -99.00  51.00 -13.00   54
  7  ω    135.00 166.00   0.50    0.05    --  103.25  51.00 -13.00   62
  8  ω     31.00  57.00   0.50    0.05    --  103.25 -51.00-159.00   52
  9  ω    -22.00  24.00   0.50    0.05    --  -47.20  19.00 -90.00   92
 10  ω    -46.00 -16.00   0.50    0.05    --  -47.20 125.00  90.00   60
 11  ω    -87.00 -55.00   0.50    0.05    --  -47.20 125.00  90.00   64
 12  ω    -27.00  30.00   0.50    0.05    --   47.20 -19.00  60.00  114
 13  ω    -91.00 -41.00   0.50    0.05    --  -99.00  77.00  90.00  100
 14  ω    -84.00 -34.00   0.50    0.05    --  -99.00  77.00-120.00  100
 15  ω   -110.00 -84.00   0.50    0.05    --  -99.00 125.00 -60.00   52
 16  ω    -58.00 -26.00   0.50    0.05    --  -99.00 125.00  90.00   64
 17  ω    -64.00 -29.00   0.50    0.05    --  -99.00  61.00-120.00   70
 18  ω    -70.00 -26.00   0.50    0.05    --  -99.00 125.00 -60.00   88
 19  ω    -61.00 -26.00   0.50    0.05    --  -99.00  61.00-180.00   70
 20  ω   -112.00 -78.00   0.50    0.05    --  -99.00 125.00-120.00   68
 21  ω   -111.00 -75.00   0.50    0.05    --  -99.00 125.00 120.00   72
 22  ω   -112.00 -27.00   0.50    0.05    --  -99.00 125.00  60.00  170
 23  ω   -105.00 -74.00   0.50    0.05    --  -99.00 125.00  90.00   62
 24  ω    126.00 166.00   0.50    0.05    --  103.25  30.00  30.00   80
 25  ω     91.00 119.00   0.50    0.05    --  103.25  30.00  30.00   56
 26  ω     32.00 103.00   0.50    0.05    --  103.25 -94.00 -30.00  142
 27  ω     55.00  81.00   0.50    0.05    --  103.25-125.00 -30.00   52
 28  ω     36.00 105.00   0.50    0.05    --  103.25-125.00 -60.00  138
 29  ω    131.00 169.00   0.50    0.05    --  103.25  15.00 -60.00   76
 30  ω     43.00  81.00   0.50    0.05    --  103.25 -94.00 120.00   76
 31  ω     55.00  93.00   0.50    0.05    --  103.25 -94.00  30.00   76
 32  ω     91.00 118.00   0.50    0.05    --  103.25  15.00 -60.00   54
 33  ω     32.00 109.00   0.50    0.05    --  103.25 -77.00 150.00  154
 34  ω     96.00 160.00   0.50    0.05    --  103.25  61.00 -90.00  128
 35  ω     91.00 154.00   0.50    0.05    --  103.25  15.00  90.00  126
 36  ω     37.00  67.00   0.50    0.05    --  103.25 -61.00   0.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0921942000
_diffrn_orient_matrix_UB_12      -0.1095977000
_diffrn_orient_matrix_UB_13      -0.0067977000
_diffrn_orient_matrix_UB_21      0.1423340000
_diffrn_orient_matrix_UB_22      -0.1507993000
_diffrn_orient_matrix_UB_23      0.0979211000
_diffrn_orient_matrix_UB_31      -0.0961425000
_diffrn_orient_matrix_UB_32      0.0297370000
_diffrn_orient_matrix_UB_33      0.1239429000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2737
_reflns_number_total             2869
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.073
_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)+(0.0501P)²+0.2337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1001
_refine_special_details          ?
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.80974(10) 0.60744(10) 0.32287(8) 0.0260(2) Uani 1 1 d . . . . .
O2 O 0.90765(17) 0.82806(14) 0.13831(10) 0.0518(3) Uani 1 1 d . . . . .
O3 O 0.87066(12) 0.96716(11) 0.28235(9) 0.0351(2) Uani 1 1 d . . . . .
N1 N 0.74758(13) 0.37639(12) 0.38894(10) 0.0274(2) Uani 1 1 d . . . . .
C1 C 0.70200(14) 0.28606(14) 0.51332(12) 0.0260(3) Uani 1 1 d . . . . .
C2 C 0.66485(16) 0.14823(15) 0.53599(14) 0.0320(3) Uani 1 1 d . . . . .
H2 H 0.669907 0.105609 0.466570 0.038 Uiso 1 1 calc R . . . .
C3 C 0.62023(16) 0.07629(15) 0.66431(15) 0.0349(3) Uani 1 1 d . . . . .
H3 H 0.593053 -0.014648 0.680526 0.042 Uiso 1 1 calc R . . . .
C4 C 0.61518(17) 0.13744(15) 0.77001(14) 0.0354(3) Uani 1 1 d . . . . .
H4 H 0.586660 0.085552 0.855800 0.042 Uiso 1 1 calc R . . . .
C5 C 0.65209(16) 0.27448(15) 0.74881(13) 0.0314(3) Uani 1 1 d . . . . .
H5 H 0.648878 0.314735 0.819507 0.038 Uiso 1 1 calc R . . . .
C6 C 0.69414(14) 0.35073(14) 0.61928(12) 0.0251(2) Uani 1 1 d . . . . .
C7 C 0.73791(14) 0.49231(14) 0.55764(11) 0.0234(2) Uani 1 1 d . . . . .
C8 C 0.76578(14) 0.49276(14) 0.41808(12) 0.0234(2) Uani 1 1 d . . . . .
C9 C 0.83216(14) 0.72222(14) 0.36360(12) 0.0244(2) Uani 1 1 d . . . . .
C10 C 0.81500(14) 0.72356(14) 0.49268(12) 0.0243(2) Uani 1 1 d . . . . .
H10 H 0.837267 0.801796 0.515343 0.029 Uiso 1 1 calc R . . . .
C11 C 0.76323(14) 0.60751(14) 0.59662(11) 0.0231(2) Uani 1 1 d . . . . .
C12 C 0.73606(14) 0.62547(13) 0.73275(11) 0.0233(2) Uani 1 1 d . . . . .
C13 C 0.58466(15) 0.63228(14) 0.79168(12) 0.0273(3) Uani 1 1 d . . . . .
H13 H 0.502578 0.618011 0.748431 0.033 Uiso 1 1 calc R . . . .
C14 C 0.55683(17) 0.66044(16) 0.91526(13) 0.0327(3) Uani 1 1 d . . . . .
H14 H 0.454735 0.667540 0.953462 0.039 Uiso 1 1 calc R . . . .
C15 C 0.68002(17) 0.67807(16) 0.98211(12) 0.0329(3) Uani 1 1 d . . . . .
H15 H 0.661244 0.695193 1.065521 0.039 Uiso 1 1 calc R . . . .
C16 C 0.83124(16) 0.67010(14) 0.92428(12) 0.0291(3) Uani 1 1 d . . . . .
H16 H 0.914333 0.681139 0.969276 0.035 Uiso 1 1 calc R . . . .
C17 C 0.85880(15) 0.64571(14) 0.79957(12) 0.0262(3) Uani 1 1 d . . . . .
H17 H 0.959418 0.642789 0.760148 0.031 Uiso 1 1 calc R . . . .
C18 C 0.87490(15) 0.84277(16) 0.24745(12) 0.0290(3) Uani 1 1 d . . . . .
C19 C 0.91691(19) 1.09063(18) 0.18058(16) 0.0411(3) Uani 1 1 d . . . . .
H19A H 0.860944 1.118870 0.092760 0.062 Uiso 1 1 calc GR . . . .
H19B H 1.037198 1.048496 0.175456 0.062 Uiso 1 1 calc GR . . . .
H19C H 0.883242 1.186409 0.206045 0.062 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C8 1.3524(14) . ?
O1 C9 1.3648(13) . ?
O2 C18 1.1956(15) . ?
O3 C18 1.3263(15) . ?
O3 C19 1.4476(15) . ?
N1 C1 1.4134(16) . ?
N1 C8 1.2952(15) . ?
C1 C2 1.3924(17) . ?
C1 C6 1.4169(16) . ?
C2 C3 1.3828(19) . ?
C3 C4 1.396(2) . ?
C4 C5 1.3865(18) . ?
C5 C6 1.3949(17) . ?
C6 C7 1.4494(16) . ?
C7 C8 1.4572(15) . ?
C7 C11 1.3696(16) . ?
C9 C10 1.3465(16) . ?
C9 C18 1.4886(17) . ?
C10 C11 1.4394(16) . ?
C11 C12 1.4781(15) . ?
C12 C13 1.3939(16) . ?
C12 C17 1.3975(16) . ?
C13 C14 1.3892(16) . ?
C14 C15 1.3865(18) . ?
C15 C16 1.3862(18) . ?
C16 C17 1.3853(16) . ?

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 C9 117.17(9) . . ?
C18 O3 C19 116.42(10) . . ?
C8 N1 C1 103.08(9) . . ?
N1 C1 C6 113.13(10) . . ?
C2 C1 N1 126.17(11) . . ?
C2 C1 C6 120.70(11) . . ?
C3 C2 C1 118.34(12) . . ?
C2 C3 C4 121.32(12) . . ?
C5 C4 C3 120.90(12) . . ?
C4 C5 C6 118.65(12) . . ?
C1 C6 C7 104.80(10) . . ?
C5 C6 C1 120.08(11) . . ?
C5 C6 C7 135.12(11) . . ?
C6 C7 C8 102.30(9) . . ?
C11 C7 C6 138.20(11) . . ?
C11 C7 C8 119.44(10) . . ?
O1 C8 C7 122.30(10) . . ?
N1 C8 O1 121.01(10) . . ?
N1 C8 C7 116.69(10) . . ?
O1 C9 C18 111.16(9) . . ?
C10 C9 O1 123.02(11) . . ?
C10 C9 C18 125.82(11) . . ?
C9 C10 C11 121.96(11) . . ?
C7 C11 C10 116.02(10) . . ?
C7 C11 C12 125.75(10) . . ?
C10 C11 C12 118.20(10) . . ?
C13 C12 C11 120.60(10) . . ?
C13 C12 C17 119.46(10) . . ?
C17 C12 C11 119.83(10) . . ?
C14 C13 C12 119.75(11) . . ?
C15 C14 C13 120.54(12) . . ?
C16 C15 C14 119.82(11) . . ?
C17 C16 C15 120.11(11) . . ?
C16 C17 C12 120.29(11) . . ?
O2 C18 O3 125.42(12) . . ?
O2 C18 C9 124.05(11) . . ?
O3 C18 C9 110.53(10) . . ?

_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.843
