# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_202207127
_audit_block_doi                 10.5517/ccdc.csd.cc2fqvkl
_database_code_depnum_ccdc_archive 'CCDC 2256290'
loop_
_audit_author_name
_audit_author_address
'Xifa Yang'
;Henan Agricultural University
China
;
_audit_update_record             
;
2023-04-14 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_audit_creation_date             2022-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 N O4'
_chemical_formula_sum            'C24 H21 N O4'
_chemical_formula_weight         387.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N1
_chemical_oxdiff_usercomment     r
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5790(3)
_cell_length_b                   13.6219(3)
_cell_length_c                   11.7844(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.869(2)
_cell_angle_gamma                90
_cell_volume                     1951.64(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4265
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8560
_cell_measurement_theta_min      3.6210
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94327
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13721
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.636
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  -4.00   1.00    1.50    --  -33.50   0.00  30.00  101
  2  ω    -94.00 -36.00   1.00    1.50    --  -33.50 -57.00-150.00   58
  3  ω    -50.00 -24.00   1.00    1.50    --  -33.50  57.00-150.00   26
  4  ω     -1.00  25.00   1.00    1.50    --  -33.50  57.00-150.00   26
  5  ω     44.00  69.00   1.00    1.50    --   36.47 -99.00-120.00   25
  6  ω     68.00 109.00   1.00    1.50    --   36.47 178.00  30.00   41
  7  ω      3.00 106.00   1.00    1.50    --   36.47  19.00 -30.00  103
  8  ω     34.00  59.00   1.00    1.50    --   36.47 -37.00 150.00   25
  9  ω      1.00  28.00   1.00    1.50    --   36.47 -99.00-120.00   27
 10  ω    -33.00   1.00   1.00    1.50    --   36.47 -37.00 150.00   34
 11  ω     23.00  72.00   1.00    1.50    --   36.47 -99.00  30.00   49
 12  ω     -2.00  76.00   1.00    1.50    --   36.47 -99.00-180.00   78
 13  ω     58.00 103.00   1.00    1.50    --   36.47 178.00-180.00   45
 14  ω     17.00 105.00   1.00    1.50    --   36.47  77.00-180.00   88
 15  ω    147.00 175.00   1.00    7.00    --  108.00  77.00-180.00   28
 16  ω     80.00 116.00   1.00    7.00    --  108.00  77.00-180.00   36
 17  ω     72.00  98.00   1.00    7.00    --  108.00 -94.00  90.00   26
 18  ω     38.00 108.00   1.00    7.00    --  108.00 -45.00 150.00   70
 19  ω     56.00 110.00   1.00    7.00    --  108.00 -94.00-150.00   54
 20  ω    101.00 176.00   1.00    7.00    --  108.00 111.00 150.00   75
 21  ω     38.00 106.00   1.00    7.00    --  108.00 -94.00 150.00   68
 22  ω     41.00 126.00   1.00    7.00    --  108.00 -61.00-120.00   85
 23  ω    106.00 134.00   1.00    7.00    --  108.00 111.00 -60.00   28
 24  ω     93.00 127.00   1.00    7.00    --  108.00 -45.00  60.00   34
 25  ω     85.00 142.00   1.00    7.00    --  108.00  77.00  90.00   57
 26  ω     71.00 108.00   1.00    7.00    --  108.00 -94.00 -60.00   37
 27  ω     43.00 126.00   1.00    7.00    --  108.00 -30.00-150.00   83
 28  ω    115.00 175.00   1.00    7.00    --  108.00  45.00-150.00   60
 29  ω    100.00 157.00   1.00    7.00    --  108.00 111.00-120.00   57
 30  ω     65.00 138.00   1.00    7.00    --  108.00-157.00 162.00   73
 31  ω     90.00 178.00   1.00    7.00    --  108.00  45.00  30.00   88
;
_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      0.0065344000
_diffrn_orient_matrix_UB_12      0.1121169000
_diffrn_orient_matrix_UB_13      0.0175998000
_diffrn_orient_matrix_UB_21      -0.1171274000
_diffrn_orient_matrix_UB_22      0.0001882000
_diffrn_orient_matrix_UB_23      0.0177915000
_diffrn_orient_matrix_UB_31      0.0479685000
_diffrn_orient_matrix_UB_32      -0.0148538000
_diffrn_orient_matrix_UB_33      0.1329119000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2821
_reflns_number_total             3476
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (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)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.041
_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)+(0.0742P)²+0.3085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1338
_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. Restrained distances
 H4-O4
 0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4A), C10(H10), C11(H11), C12(H12), C13(H13),
 C18(H18), C20(H20)
3.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.92316(11) 0.71041(10) 0.81381(10) 0.0440(3) Uani 1 1 d . . . . .
O2 O 0.76561(12) 0.78053(11) 0.81115(11) 0.0521(4) Uani 1 1 d . . . . .
O3 O 0.75596(9) 0.59309(8) 0.64243(10) 0.0352(3) Uani 1 1 d . . . . .
O4 O 0.35805(13) 0.45066(13) 0.6818(2) 0.0739(6) Uani 1 1 d D . . . .
H4 H 0.360(3) 0.3892(14) 0.701(3) 0.094(11) Uiso 1 1 d D . . . .
N1 N 0.86098(12) 0.70827(11) 0.57527(12) 0.0342(3) Uani 1 1 d . . . . .
H1 H 0.8402(16) 0.7036(15) 0.499(2) 0.039(5) Uiso 1 1 d . . . . .
C1 C 1.08263(16) 0.61500(17) 0.81619(17) 0.0507(5) Uani 1 1 d . . . . .
H1A H 1.1007 0.6158 0.8978 0.061 Uiso 1 1 calc R . . . .
C2 C 1.14952(16) 0.56779(17) 0.7572(2) 0.0555(5) Uani 1 1 d . . . . .
H2 H 1.2129 0.5359 0.7990 0.067 Uiso 1 1 calc R . . . .
C3 C 1.12224(16) 0.56796(16) 0.6358(2) 0.0505(5) Uani 1 1 d . . . . .
H3 H 1.1676 0.5363 0.5963 0.061 Uiso 1 1 calc R . . . .
C4 C 1.02788(15) 0.61489(14) 0.57264(16) 0.0424(4) Uani 1 1 d . . . . .
H4A H 1.0107 0.6154 0.4910 0.051 Uiso 1 1 calc R . . . .
C5 C 0.95908(13) 0.66105(12) 0.63088(15) 0.0348(4) Uani 1 1 d . . . . .
C6 C 0.98868(14) 0.66094(13) 0.75239(15) 0.0386(4) Uani 1 1 d . . . . .
C7 C 0.81885(15) 0.73439(13) 0.75867(14) 0.0364(4) Uani 1 1 d . . . . .
C8 C 0.77446(13) 0.69702(12) 0.63176(13) 0.0321(4) Uani 1 1 d . . . . .
C9 C 0.67197(14) 0.75165(12) 0.56854(14) 0.0340(4) Uani 1 1 d . . . . .
C10 C 0.68150(17) 0.84258(14) 0.51826(17) 0.0454(4) Uani 1 1 d . . . . .
H10 H 0.7507 0.8694 0.5244 0.054 Uiso 1 1 calc R . . . .
C11 C 0.58876(19) 0.89305(16) 0.4594(2) 0.0555(5) Uani 1 1 d . . . . .
H11 H 0.5952 0.9540 0.4263 0.067 Uiso 1 1 calc R . . . .
C12 C 0.48649(18) 0.85250(16) 0.44997(19) 0.0550(5) Uani 1 1 d . . . . .
H12 H 0.4238 0.8860 0.4094 0.066 Uiso 1 1 calc R . . . .
C13 C 0.47616(16) 0.76281(15) 0.50006(17) 0.0458(4) Uani 1 1 d . . . . .
H13 H 0.4065 0.7366 0.4929 0.055 Uiso 1 1 calc R . . . .
C14 C 0.56929(14) 0.71043(13) 0.56177(14) 0.0355(4) Uani 1 1 d . . . . .
C15 C 0.56144(14) 0.61449(12) 0.61712(14) 0.0346(4) Uani 1 1 d . . . . .
C16 C 0.65684(13) 0.55913(12) 0.65795(13) 0.0319(4) Uani 1 1 d . . . . .
C17 C 0.65606(14) 0.46601(12) 0.70849(14) 0.0346(4) Uani 1 1 d . . . . .
C18 C 0.55425(15) 0.42988(13) 0.71467(16) 0.0407(4) Uani 1 1 d . . . . .
H18 H 0.5503 0.3679 0.7463 0.049 Uiso 1 1 calc R . . . .
C19 C 0.45872(15) 0.48387(15) 0.67491(18) 0.0456(4) Uani 1 1 d . . . . .
C20 C 0.46211(15) 0.57593(14) 0.62798(18) 0.0435(4) Uani 1 1 d . . . . .
H20 H 0.3979 0.6125 0.6035 0.052 Uiso 1 1 calc R . . . .
C21 C 0.76277(15) 0.40744(14) 0.75850(17) 0.0423(4) Uani 1 1 d . . . . .
C22 C 0.82269(19) 0.38654(17) 0.6625(2) 0.0566(5) Uani 1 1 d . . . . .
H22A H 0.7767 0.3469 0.6021 0.085 Uiso 1 1 calc GR . . . .
H22B H 0.8901 0.3522 0.6962 0.085 Uiso 1 1 calc GR . . . .
H22C H 0.8387 0.4474 0.6294 0.085 Uiso 1 1 calc GR . . . .
C23 C 0.83849(17) 0.46522(17) 0.85881(19) 0.0547(5) Uani 1 1 d . . . . .
H23A H 0.8565 0.5272 0.8297 0.082 Uiso 1 1 calc GR . . . .
H23B H 0.9047 0.4285 0.8899 0.082 Uiso 1 1 calc GR . . . .
H23C H 0.8017 0.4762 0.9197 0.082 Uiso 1 1 calc GR . . . .
C24 C 0.73976(19) 0.30859(16) 0.8093(2) 0.0605(6) Uani 1 1 d . . . . .
H24A H 0.7056 0.3195 0.8723 0.091 Uiso 1 1 calc GR . . . .
H24B H 0.8077 0.2738 0.8385 0.091 Uiso 1 1 calc GR . . . .
H24C H 0.6916 0.2705 0.7490 0.091 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 C6 1.401(2) . ?
O1 C7 1.346(2) . ?
O2 C7 1.200(2) . ?
O3 C8 1.445(2) . ?
O3 C16 1.385(2) . ?
O4 H4 0.868(18) . ?
O4 C19 1.367(2) . ?
N1 H1 0.87(2) . ?
N1 C5 1.397(2) . ?
N1 C8 1.422(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C6 1.377(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4A 0.9300 . ?
C4 C5 1.386(3) . ?
C5 C6 1.384(2) . ?
C7 C8 1.542(2) . ?
C8 C9 1.509(2) . ?
C9 C10 1.391(3) . ?
C9 C14 1.392(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.405(2) . ?
C14 C15 1.475(2) . ?
C15 C16 1.394(2) . ?
C15 C20 1.391(3) . ?
C16 C17 1.402(2) . ?
C17 C18 1.391(2) . ?
C17 C21 1.543(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C19 C20 1.376(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.538(3) . ?
C21 C23 1.532(3) . ?
C21 C24 1.531(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C7 O1 C6 119.79(13) . . ?
C16 O3 C8 120.60(12) . . ?
C19 O4 H4 112(2) . . ?
C5 N1 H1 116.5(14) . . ?
C5 N1 C8 114.89(13) . . ?
C8 N1 H1 114.2(13) . . ?
C2 C1 H1A 120.5 . . ?
C6 C1 H1A 120.5 . . ?
C6 C1 C2 119.03(18) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.92(18) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.50(19) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4A 120.0 . . ?
C3 C4 C5 120.09(17) . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 N1 124.43(15) . . ?
C6 C5 N1 117.17(16) . . ?
C6 C5 C4 118.40(16) . . ?
C1 C6 O1 118.20(16) . . ?
C1 C6 C5 122.04(18) . . ?
C5 C6 O1 119.75(16) . . ?
O1 C7 C8 116.96(14) . . ?
O2 C7 O1 118.83(15) . . ?
O2 C7 C8 124.18(16) . . ?
O3 C8 C7 105.38(13) . . ?
O3 C8 C9 112.93(13) . . ?
N1 C8 O3 107.81(13) . . ?
N1 C8 C7 106.75(13) . . ?
N1 C8 C9 112.04(13) . . ?
C9 C8 C7 111.52(14) . . ?
C10 C9 C8 119.54(16) . . ?
C10 C9 C14 120.98(16) . . ?
C14 C9 C8 119.47(15) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.27(19) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.52(18) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.65(18) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.97(18) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 C13 117.59(16) . . ?
C9 C14 C15 119.90(15) . . ?
C13 C14 C15 122.51(17) . . ?
C16 C15 C14 118.85(15) . . ?
C20 C15 C14 122.60(16) . . ?
C20 C15 C16 118.54(16) . . ?
O3 C16 C15 119.86(15) . . ?
O3 C16 C17 117.56(14) . . ?
C15 C16 C17 122.45(15) . . ?
C16 C17 C21 121.99(15) . . ?
C18 C17 C16 116.68(16) . . ?
C18 C17 C21 121.30(16) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.69(17) . . ?
C19 C18 H18 119.2 . . ?
O4 C19 C18 122.77(18) . . ?
O4 C19 C20 116.78(17) . . ?
C20 C19 C18 120.44(17) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.16(17) . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C17 110.94(16) . . ?
C23 C21 C17 109.68(15) . . ?
C23 C21 C22 109.73(18) . . ?
C24 C21 C17 111.77(16) . . ?
C24 C21 C22 107.59(17) . . ?
C24 C21 C23 107.03(17) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
O4 H4 O2 0.868(18) 2.14(3) 2.804(2) 133(3) 2_646
N1 H1 O1 0.87(2) 2.90(2) 3.5454(18) 132.5(16) 4_575
N1 H1 O2 0.87(2) 2.18(2) 3.0387(19) 167.5(19) 4_575

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 C7 C8 O3 73.71(18) . . . . ?
O1 C7 C8 N1 -40.75(19) . . . . ?
O1 C7 C8 C9 -163.42(15) . . . . ?
O2 C7 C8 O3 -104.21(19) . . . . ?
O2 C7 C8 N1 141.34(18) . . . . ?
O2 C7 C8 C9 18.7(2) . . . . ?
O3 C8 C9 C10 -159.44(15) . . . . ?
O3 C8 C9 C14 20.8(2) . . . . ?
O3 C16 C17 C18 -174.98(14) . . . . ?
O3 C16 C17 C21 6.9(2) . . . . ?
O4 C19 C20 C15 -179.46(19) . . . . ?
N1 C5 C6 O1 -2.6(2) . . . . ?
N1 C5 C6 C1 178.78(17) . . . . ?
N1 C8 C9 C10 -37.5(2) . . . . ?
N1 C8 C9 C14 142.75(16) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C1 C6 O1 -178.55(18) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 N1 -178.43(17) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C4 C5 C6 O1 177.41(16) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C5 N1 C8 O3 -56.40(17) . . . . ?
C5 N1 C8 C7 56.40(18) . . . . ?
C5 N1 C8 C9 178.74(14) . . . . ?
C6 O1 C7 O2 -176.73(17) . . . . ?
C6 O1 C7 C8 5.2(2) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C7 O1 C6 C1 -163.19(17) . . . . ?
C7 O1 C6 C5 18.1(2) . . . . ?
C7 C8 C9 C10 82.12(19) . . . . ?
C7 C8 C9 C14 -97.66(18) . . . . ?
C8 O3 C16 C15 26.2(2) . . . . ?
C8 O3 C16 C17 -157.73(14) . . . . ?
C8 N1 C5 C4 142.69(17) . . . . ?
C8 N1 C5 C6 -37.3(2) . . . . ?
C8 C9 C10 C11 179.47(17) . . . . ?
C8 C9 C14 C13 -178.72(15) . . . . ?
C8 C9 C14 C15 0.5(2) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C9 C14 C15 C16 -10.8(2) . . . . ?
C9 C14 C15 C20 170.66(17) . . . . ?
C10 C9 C14 C13 1.5(3) . . . . ?
C10 C9 C14 C15 -179.23(16) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C9 -1.1(3) . . . . ?
C12 C13 C14 C15 179.65(18) . . . . ?
C13 C14 C15 C16 168.46(16) . . . . ?
C13 C14 C15 C20 -10.1(3) . . . . ?
C14 C9 C10 C11 -0.7(3) . . . . ?
C14 C15 C16 O3 -2.2(2) . . . . ?
C14 C15 C16 C17 -178.09(15) . . . . ?
C14 C15 C20 C19 176.65(17) . . . . ?
C15 C16 C17 C18 1.0(2) . . . . ?
C15 C16 C17 C21 -177.15(15) . . . . ?
C16 O3 C8 N1 -158.95(13) . . . . ?
C16 O3 C8 C7 87.33(16) . . . . ?
C16 O3 C8 C9 -34.63(19) . . . . ?
C16 C15 C20 C19 -1.9(3) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
C16 C17 C21 C22 -60.3(2) . . . . ?
C16 C17 C21 C23 61.1(2) . . . . ?
C16 C17 C21 C24 179.61(17) . . . . ?
C17 C18 C19 O4 -178.9(2) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C17 C21 C22 121.65(19) . . . . ?
C18 C17 C21 C23 -116.97(19) . . . . ?
C18 C17 C21 C24 1.6(3) . . . . ?
C18 C19 C20 C15 1.8(3) . . . . ?
C20 C15 C16 O3 176.39(15) . . . . ?
C20 C15 C16 C17 0.5(3) . . . . ?
C21 C17 C18 C19 176.99(17) . . . . ?

_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 1.078
_oxdiff_exptl_absorpt_empirical_full_min 0.933
