# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_lg202007hbx7
_database_code_depnum_ccdc_archive 'CCDC 2014074'
loop_
_audit_author_name
_audit_author_address
'Gang Li'
;Zhengzhou University
China
;
_audit_update_record             
;
2022-03-14 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_audit_creation_date             2020-07-02
_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 H15 N3 O6, 4(H2 O)'
_chemical_formula_sum            'C24 H23 N3 O10'
_chemical_formula_weight         513.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O4Ce1
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/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   7.9842(3)
_cell_length_b                   18.7164(7)
_cell_length_c                   15.8121(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.417(3)
_cell_angle_gamma                90
_cell_volume                     2360.78(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2252
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8960
_cell_measurement_theta_min      4.7000
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.971
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27035
_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            'clear violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8515
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.056
_diffrn_reflns_theta_max         67.056
_diffrn_reflns_theta_min         3.661
_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   -104.00 -11.00   1.00    6.00    --  -33.50 -37.00 -30.00   93
  2  ω   -105.00 -79.00   1.00    6.00    --  -33.50 178.00  30.00   26
  3  ω     26.00  73.00   1.00    6.00    --   36.47 -99.00  90.00   47
  4  ω     16.00 106.00   1.00    6.00    --   36.47  77.00 -90.00   90
  5  ω     -2.00  33.00   1.00    6.00    --   36.47 -99.00 -30.00   35
  6  ω     57.00  83.00   1.00    6.00    --   36.47 178.00 120.00   26
  7  ω     12.00  86.00   1.00    6.00    --   36.47  77.00-150.00   74
  8  ω     93.00 125.00   1.00   12.00    --  108.00  61.00  30.00   32
  9  ω    110.00 157.00   1.00   12.00    --  108.00 111.00  60.00   47
 10  ω     39.00 112.00   1.00   12.00    --  108.00-111.00-120.00   73
 11  ω     60.00 122.00   1.00   12.00    --  108.00 -61.00 -90.00   62
 12  ω     49.00  98.00   1.00   12.00    --  108.00 -94.00  60.00   49
 13  ω    138.00 176.00   1.00   12.00    --  108.00  61.00  30.00   38
 14  ω    100.00 138.00   1.00   12.00    --  108.00 111.00   0.00   38
 15  ω     41.00 104.00   1.00   12.00    --  108.00 -94.00 -90.00   63
 16  ω     72.00 150.00   1.00   12.00    --  108.00  15.00 120.00   78
;
_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      0.0172683000
_diffrn_orient_matrix_UB_12      -0.0438163000
_diffrn_orient_matrix_UB_13      -0.0816612000
_diffrn_orient_matrix_UB_21      0.0359096000
_diffrn_orient_matrix_UB_22      0.0691774000
_diffrn_orient_matrix_UB_23      -0.0489432000
_diffrn_orient_matrix_UB_31      0.1889852000
_diffrn_orient_matrix_UB_32      -0.0091014000
_diffrn_orient_matrix_UB_33      0.0209911000
_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                3050
_reflns_number_total             4219
_reflns_odcompleteness_completeness 99.73
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4219
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0658
_refine_ls_restrained_S_all      1.028
_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)+(0.1036P)²+1.0507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1769
_refine_ls_wR_factor_ref         0.2002
_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 O(H) groups, All O(H,H) groups
2. Restrained distances
 O9-H9A
 0.9 with sigma of 0.02
 O9-H9B
 0.9 with sigma of 0.02
3.a Riding coordinates:
 O7(H7A,H7B), O10(H10A,H10B)
3.b Free rotating group:
 O8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 -0.0141(3) 0.78378(13) 0.59761(15) 0.0560(6) Uani 1 1 d . . . . .
O2 O 0.0738(4) 0.70254(13) 0.69103(14) 0.0625(7) Uani 1 1 d . . . . .
H2 H 0.0180 0.7264 0.7229 0.094 Uiso 1 1 calc GR . . . .
O3 O 0.1706(3) 0.46232(12) 0.55387(15) 0.0543(6) Uani 1 1 d . . . . .
O4 O 0.2973(4) 0.46396(12) 0.43104(16) 0.0621(7) Uani 1 1 d . . . . .
O5 O 0.5868(3) 0.74235(15) 0.40282(17) 0.0628(7) Uani 1 1 d . . . . .
O6 O 0.3998(3) 0.72771(16) 0.29693(15) 0.0663(7) Uani 1 1 d . . . . .
O7 O 0.3217(4) 0.32589(14) 0.4344(2) 0.0836(10) Uani 1 1 d . . . . .
H7A H 0.3495 0.3009 0.4777 0.125 Uiso 1 1 d R . . . .
H7B H 0.3316 0.3718 0.4276 0.125 Uiso 1 1 d R . . . .
O8 O 0.4092(5) 0.2439(3) 0.2901(3) 0.1142(14) Uani 1 1 d . . . . .
H8A H 0.4155 0.2872 0.3059 0.171 Uiso 1 1 d G . . . .
H8B H 0.3167 0.2369 0.2628 0.171 Uiso 1 1 d G . . . .
O9 O 0.8883(6) 0.6823(3) 0.3439(4) 0.1369(18) Uani 1 1 d D . . . .
H9A H 0.84(3) 0.721(7) 0.318(13) 0.52(15) Uiso 1 1 d D . . . .
H9B H 0.81(2) 0.686(15) 0.384(12) 0.7(2) Uiso 1 1 d D . . . .
N1 N 0.3873(3) 1.03321(13) 0.60881(16) 0.0393(6) Uani 1 1 d . . . . .
H1 H 0.3244 1.0494 0.5677 0.047 Uiso 1 1 calc R . . . .
N2 N 0.2470(3) 0.95309(12) 0.48524(14) 0.0349(5) Uani 1 1 d . . . . .
N3 N 0.0545(4) 1.02739(15) 0.36508(19) 0.0535(7) Uani 1 1 d . . . . .
H3 H 0.0986 1.0495 0.4082 0.064 Uiso 1 1 calc R . . . .
C1 C 0.0623(4) 0.72980(15) 0.61521(19) 0.0390(7) Uani 1 1 d . . . . .
C2 C 0.2304(4) 0.49480(16) 0.49610(19) 0.0407(7) Uani 1 1 d . . . . .
C3 C 0.4490(4) 0.72161(15) 0.37230(19) 0.0404(7) Uani 1 1 d . . . . .
C4 C 0.1578(3) 0.68814(14) 0.55220(17) 0.0327(6) Uani 1 1 d . . . . .
C5 C 0.1544(3) 0.61376(14) 0.55300(17) 0.0347(6) Uani 1 1 d . . . . .
H5 H 0.0966 0.5901 0.5945 0.042 Uiso 1 1 calc R . . . .
C6 C 0.2358(3) 0.57464(15) 0.49313(17) 0.0345(6) Uani 1 1 d . . . . .
C7 C 0.3264(4) 0.61037(15) 0.43268(18) 0.0368(6) Uani 1 1 d . . . . .
H7 H 0.3823 0.5843 0.3925 0.044 Uiso 1 1 calc R . . . .
C8 C 0.3338(3) 0.68441(14) 0.43199(17) 0.0333(6) Uani 1 1 d . . . . .
C9 C 0.2484(3) 0.72392(15) 0.49144(16) 0.0325(6) Uani 1 1 d . . . . .
C10 C 0.4512(4) 1.07966(17) 0.6658(2) 0.0478(8) Uani 1 1 d . . . . .
H10 H 0.4281 1.1282 0.6601 0.057 Uiso 1 1 calc R . . . .
C11 C 0.5504(4) 1.05586(19) 0.7323(2) 0.0507(8) Uani 1 1 d . . . . .
H11 H 0.5942 1.0876 0.7728 0.061 Uiso 1 1 calc R . . . .
C12 C 0.5843(4) 0.9837(2) 0.7382(2) 0.0547(9) Uani 1 1 d . . . . .
H12 H 0.6525 0.9665 0.7828 0.066 Uiso 1 1 calc R . . . .
C13 C 0.5177(4) 0.93706(18) 0.6784(2) 0.0474(7) Uani 1 1 d . . . . .
H13 H 0.5410 0.8885 0.6825 0.057 Uiso 1 1 calc R . . . .
C14 C 0.4166(3) 0.96255(15) 0.61264(18) 0.0359(6) Uani 1 1 d . . . . .
C15 C 0.3329(3) 0.91722(15) 0.54641(17) 0.0338(6) Uani 1 1 d . . . . .
C16 C 0.3412(3) 0.84341(15) 0.55059(17) 0.0355(6) Uani 1 1 d . . . . .
H16 H 0.4040 0.8207 0.5936 0.043 Uiso 1 1 calc R . . . .
C17 C 0.2535(3) 0.80416(15) 0.48892(17) 0.0329(6) Uani 1 1 d . . . . .
C18 C 0.1662(3) 0.84034(15) 0.42469(18) 0.0361(6) Uani 1 1 d . . . . .
H18 H 0.1087 0.8153 0.3818 0.043 Uiso 1 1 calc R . . . .
C19 C 0.1657(3) 0.91494(15) 0.42526(17) 0.0343(6) Uani 1 1 d . . . . .
C20 C 0.0701(3) 0.95528(16) 0.35769(18) 0.0378(6) Uani 1 1 d . . . . .
C21 C 0.0045(4) 0.91892(17) 0.2902(2) 0.0460(7) Uani 1 1 d . . . . .
H21 H 0.0173 0.8697 0.2860 0.055 Uiso 1 1 calc R . . . .
C22 C -0.0807(5) 0.9563(2) 0.2288(2) 0.0669(11) Uani 1 1 d . . . . .
H22 H -0.1264 0.9320 0.1821 0.080 Uiso 1 1 calc R . . . .
C23 C -0.1018(4) 1.0292(2) 0.2336(2) 0.0608(10) Uani 1 1 d . . . . .
H23 H -0.1611 1.0540 0.1911 0.073 Uiso 1 1 calc R . . . .
C24 C -0.0329(5) 1.0640(2) 0.3026(2) 0.0573(9) Uani 1 1 d . . . . .
H24 H -0.0455 1.1132 0.3071 0.069 Uiso 1 1 calc R . . . .
O10 O 0.7611(4) 0.8712(3) 0.4999(3) 0.1325(19) Uani 1 1 d . . . . .
H10A H 0.6869 0.8312 0.4989 0.199 Uiso 1 1 d R . . . .
H10B H 0.8516 0.8517 0.5182 0.199 Uiso 1 1 d 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 C1 1.206(4) . ?
O2 H2 0.8200 . ?
O2 C1 1.303(4) . ?
O3 C2 1.212(4) . ?
O4 C2 1.312(4) . ?
O5 C3 1.245(4) . ?
O6 C3 1.244(4) . ?
O7 H7A 0.8502 . ?
O7 H7B 0.8696 . ?
O8 H8A 0.8492 . ?
O8 H8B 0.8493 . ?
O9 H9A 0.91(2) . ?
O9 H9B 0.91(2) . ?
N1 H1 0.8600 . ?
N1 C10 1.338(4) . ?
N1 C14 1.344(4) . ?
N2 C15 1.342(4) . ?
N2 C19 1.334(4) . ?
N3 H3 0.8600 . ?
N3 C20 1.361(4) . ?
N3 C24 1.369(4) . ?
C1 C4 1.499(4) . ?
C2 C6 1.496(4) . ?
C3 C8 1.514(4) . ?
C4 C5 1.392(4) . ?
C4 C9 1.397(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(4) . ?
C6 C7 1.394(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(4) . ?
C8 C9 1.397(4) . ?
C9 C17 1.503(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(4) . ?
C14 C15 1.484(4) . ?
C15 C16 1.385(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(4) . ?
C17 C18 1.384(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.396(4) . ?
C19 C20 1.492(4) . ?
C20 C21 1.353(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.356(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.366(6) . ?
C24 H24 0.9300 . ?
O10 H10A 0.9544 . ?
O10 H10B 0.8492 . ?

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
C1 O2 H2 109.5 . . ?
H7A O7 H7B 128.3 . . ?
H8A O8 H8B 109.6 . . ?
H9A O9 H9B 88(10) . . ?
C10 N1 H1 118.4 . . ?
C10 N1 C14 123.3(3) . . ?
C14 N1 H1 118.4 . . ?
C19 N2 C15 117.6(2) . . ?
C20 N3 H3 120.7 . . ?
C20 N3 C24 118.7(3) . . ?
C24 N3 H3 120.7 . . ?
O1 C1 O2 123.8(3) . . ?
O1 C1 C4 123.3(3) . . ?
O2 C1 C4 112.9(2) . . ?
O3 C2 O4 123.8(3) . . ?
O3 C2 C6 122.5(3) . . ?
O4 C2 C6 113.7(3) . . ?
O5 C3 C8 116.8(3) . . ?
O6 C3 O5 125.5(3) . . ?
O6 C3 C8 117.6(3) . . ?
C5 C4 C1 120.2(2) . . ?
C5 C4 C9 119.7(2) . . ?
C9 C4 C1 120.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C2 119.6(3) . . ?
C5 C6 C7 119.2(3) . . ?
C7 C6 C2 121.1(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C3 119.4(2) . . ?
C7 C8 C9 120.1(3) . . ?
C9 C8 C3 120.2(2) . . ?
C4 C9 C17 120.8(2) . . ?
C8 C9 C4 119.4(3) . . ?
C8 C9 C17 119.8(2) . . ?
N1 C10 H10 120.0 . . ?
N1 C10 C11 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.5(3) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
N1 C14 C13 118.1(3) . . ?
N1 C14 C15 117.3(3) . . ?
C13 C14 C15 124.6(3) . . ?
N2 C15 C14 115.1(2) . . ?
N2 C15 C16 123.8(3) . . ?
C16 C15 C14 121.2(3) . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.2(3) . . ?
C17 C16 H16 120.9 . . ?
C16 C17 C9 121.6(2) . . ?
C18 C17 C9 119.7(2) . . ?
C18 C17 C16 118.7(3) . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.1(3) . . ?
C19 C18 H18 120.5 . . ?
N2 C19 C18 122.6(3) . . ?
N2 C19 C20 117.2(2) . . ?
C18 C19 C20 120.2(2) . . ?
N3 C20 C19 119.1(3) . . ?
C21 C20 N3 122.2(3) . . ?
C21 C20 C19 118.7(3) . . ?
C20 C21 H21 121.0 . . ?
C20 C21 C22 118.1(3) . . ?
C22 C21 H21 121.0 . . ?
C21 C22 H22 119.0 . . ?
C21 C22 C23 122.1(3) . . ?
C23 C22 H22 119.0 . . ?
C22 C23 H23 121.0 . . ?
C24 C23 C22 118.1(3) . . ?
C24 C23 H23 121.0 . . ?
N3 C24 H24 119.6 . . ?
C23 C24 N3 120.9(3) . . ?
C23 C24 H24 119.6 . . ?
H10A O10 H10B 100.8 . . ?

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
O2 H2 O6 0.82 1.76 2.576(3) 175.6 4_576
O7 H7B O4 0.87 1.75 2.592(4) 162.9 .
O8 H8A O7 0.85 2.31 2.860(6) 122.7 .
O8 H8B O6 0.85 1.94 2.790(5) 175.9 2_545
O9 H9B O5 0.91(2) 2.11(18) 2.849(5) 138(23) .
N1 H1 O10 0.86 1.94 2.718(4) 150.2 3_676
O10 H10B O1 0.85 2.06 2.837(4) 152.6 1_655

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 C1 C4 C5 -140.0(3) . . . . ?
O1 C1 C4 C9 38.9(4) . . . . ?
O2 C1 C4 C5 41.5(4) . . . . ?
O2 C1 C4 C9 -139.5(3) . . . . ?
O3 C2 C6 C5 -7.1(4) . . . . ?
O3 C2 C6 C7 170.6(3) . . . . ?
O4 C2 C6 C5 173.3(3) . . . . ?
O4 C2 C6 C7 -9.0(4) . . . . ?
O5 C3 C8 C7 -99.2(3) . . . . ?
O5 C3 C8 C9 74.7(4) . . . . ?
O6 C3 C8 C7 79.5(4) . . . . ?
O6 C3 C8 C9 -106.7(3) . . . . ?
N1 C10 C11 C12 1.0(5) . . . . ?
N1 C14 C15 N2 5.3(4) . . . . ?
N1 C14 C15 C16 -172.9(3) . . . . ?
N2 C15 C16 C17 -1.1(4) . . . . ?
N2 C19 C20 N3 -7.2(4) . . . . ?
N2 C19 C20 C21 171.6(3) . . . . ?
N3 C20 C21 C22 -0.6(5) . . . . ?
C1 C4 C5 C6 177.2(3) . . . . ?
C1 C4 C9 C8 -178.6(3) . . . . ?
C1 C4 C9 C17 0.8(4) . . . . ?
C2 C6 C7 C8 -178.3(3) . . . . ?
C3 C8 C9 C4 -172.8(3) . . . . ?
C3 C8 C9 C17 7.7(4) . . . . ?
C4 C5 C6 C2 179.7(3) . . . . ?
C4 C5 C6 C7 1.9(4) . . . . ?
C4 C9 C17 C16 71.0(3) . . . . ?
C4 C9 C17 C18 -107.7(3) . . . . ?
C5 C4 C9 C8 0.3(4) . . . . ?
C5 C4 C9 C17 179.7(3) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C6 C7 C8 C3 173.0(3) . . . . ?
C6 C7 C8 C9 -0.9(4) . . . . ?
C7 C8 C9 C4 1.0(4) . . . . ?
C7 C8 C9 C17 -178.5(3) . . . . ?
C8 C9 C17 C16 -109.5(3) . . . . ?
C8 C9 C17 C18 71.8(3) . . . . ?
C9 C4 C5 C6 -1.7(4) . . . . ?
C9 C17 C18 C19 177.1(2) . . . . ?
C10 N1 C14 C13 -0.2(4) . . . . ?
C10 N1 C14 C15 178.2(3) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 N1 0.6(5) . . . . ?
C12 C13 C14 C15 -177.6(3) . . . . ?
C13 C14 C15 N2 -176.5(3) . . . . ?
C13 C14 C15 C16 5.3(4) . . . . ?
C14 N1 C10 C11 -0.6(5) . . . . ?
C14 C15 C16 C17 176.9(2) . . . . ?
C15 N2 C19 C18 0.6(4) . . . . ?
C15 N2 C19 C20 179.8(2) . . . . ?
C15 C16 C17 C9 -176.7(2) . . . . ?
C15 C16 C17 C18 2.0(4) . . . . ?
C16 C17 C18 C19 -1.7(4) . . . . ?
C17 C18 C19 N2 0.3(4) . . . . ?
C17 C18 C19 C20 -178.9(2) . . . . ?
C18 C19 C20 N3 172.0(3) . . . . ?
C18 C19 C20 C21 -9.2(4) . . . . ?
C19 N2 C15 C14 -178.3(2) . . . . ?
C19 N2 C15 C16 -0.2(4) . . . . ?
C19 C20 C21 C22 -179.4(3) . . . . ?
C20 N3 C24 C23 -0.7(5) . . . . ?
C20 C21 C22 C23 -0.1(6) . . . . ?
C21 C22 C23 C24 0.4(6) . . . . ?
C22 C23 C24 N3 0.0(5) . . . . ?
C24 N3 C20 C19 179.7(3) . . . . ?
C24 N3 C20 C21 1.0(5) . . . . ?

_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 3.421
_oxdiff_exptl_absorpt_empirical_full_min 0.719
