# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_202307171_auto
_database_code_depnum_ccdc_archive 'CCDC 2408880'
loop_
_audit_author_name
_audit_author_address
'Mei guangjian'
;JiangSu normal universtiy
China
;
_audit_update_record             
;
2024-12-10 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_date             2023-07-06
_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         'C18 H25 N3 O4, H2 O'
_chemical_formula_sum            'C18 H27 N3 O5'
_chemical_formula_weight         365.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H28O4N2
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.5356(3)
_cell_length_b                   11.5149(5)
_cell_length_c                   11.9517(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.104(4)
_cell_angle_gamma                90
_cell_volume                     1001.25(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4739
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3930
_cell_measurement_theta_min      3.8220
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10486
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.515
_diffrn_reflns_theta_min         3.831
_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 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00 120.00   73
  2  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00-180.00   73
  3  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00   0.00   87
  4  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00-150.00   73
  5  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00   0.00   73
  6  ω     38.00 128.00   1.00    3.50    --  108.00 -45.00-150.00   90
  7  ω    122.00 173.00   1.00    3.50    --  108.00  45.00 120.00   51
  8  ω    116.00 142.00   1.00    3.50    --  108.00  77.00-150.00   26
  9  ω     52.00 104.00   1.00    3.50    --  108.00 -94.00 120.00   52
 10  ω     42.00 107.00   1.00    3.50    --  108.00 -94.00-150.00   65
 11  ω     65.00 163.00   1.00    3.50    --  108.00  15.00  60.00   98
 12  ω     58.00 106.00   1.00    3.50    --  108.00 -94.00 -60.00   48
 13  ω     74.00 127.00   1.00    3.50    --  108.00 -61.00 -90.00   53
 14  ω    -72.00 -18.00   1.00    2.00    --  -33.50 -37.00   0.00   54
 15  ω    -97.00 -46.00   1.00    2.00    --  -33.50 178.00 -90.00   51
 16  ω    -77.00 -51.00   1.00    2.00    --  -33.50 -57.00  30.00   26
 17  ω    -83.00 -57.00   1.00    2.00    --  -33.50 -37.00 150.00   26
 18  ω   -104.00 -11.00   1.00    2.00    --  -33.50 -37.00  60.00   93
 19  ω    -48.00  -9.00   1.00    2.00    --  -33.50 -70.00  77.95   39
 20  ω     83.00 109.00   1.00    3.50    --  108.00  30.00  60.00   26
 21  ω     90.00 116.00   1.00    3.50    --  108.00  61.00 150.00   26
 22  ω     82.00 108.00   1.00    3.50    --  108.00  30.00 150.00   26
 23  ω     89.00 115.00   1.00    3.50    --  108.00  45.00  30.00   26
 24  ω     91.00 131.00   1.00    3.50    --  108.00  61.00  90.00   40
 25  ω     90.00 117.00   1.00    3.50    --  108.00  61.00 120.00   27
 26  ω     89.00 115.00   1.00    3.50    --  108.00  61.00  30.00   26
 27  ω     89.00 115.00   1.00    3.50    --  108.00  45.00  90.00   26
 28  ω     89.00 115.00   1.00    3.50    --  108.00  45.00 150.00   26
 29  ω    128.00 154.00   1.00    3.50    --  108.00  45.00  60.00   26
 30  ω     94.00 120.00   1.00    3.50    --  108.00  45.00-180.00   26
 31  ω     85.00 111.00   1.00    3.50    --  108.00  30.00  90.00   26
 32  ω     88.00 121.00   1.00    3.50    --  108.00  45.00 120.00   33
 33  ω     87.00 113.00   1.00    3.50    --  108.00  30.00-180.00   26
 34  ω     88.00 113.00   1.00    3.50    --  108.00  61.00  60.00   25
 35  ω     88.00 114.00   1.00    3.50    --  108.00  45.00  60.00   26
 36  ω     87.00 144.00   1.00    3.50    --  108.00  30.00 120.00   57
 37  ω     60.00 150.00   1.00    3.50    --  108.00 -15.00 -90.00   90
 38  ω    -77.00 -51.00   1.00    2.00    --  -33.50 -57.00  30.00   26
 39  ω    -68.00 -17.00   1.00    2.00    --  -33.50 -32.00 -16.75   51
 40  ω     18.00  44.00   1.00    2.00    --   36.47  57.00 -60.00   26
 41  ω    152.00 178.00   1.00    3.50    --  108.00  45.00 -60.00   26
 42  ω    121.00 147.00   1.00    3.50    --  108.00 -15.00 150.00   26
 43  ω    109.00 141.00   1.00    3.50    --  108.00 111.00 150.00   32
 44  ω     50.00  91.00   1.00    3.50    --  108.00 -15.00 150.00   41
 45  ω     56.00 118.00   1.00    3.50    --  108.00 -77.00 -60.00   62
 46  ω     46.00  89.00   1.00    3.50    --  108.00-111.00 -60.00   43
 47  ω     64.00  96.00   1.00    3.50    --  108.00 178.00  60.00   32
 48  ω     88.00 114.00   1.00    3.50    --  108.00  30.00 120.00   26
 49  ω     57.00  94.00   1.00    3.50    --  108.00 -94.00  90.00   37
 50  ω     51.00  81.00   1.00    3.50    --  108.00-111.00-150.00   30
 51  ω     93.00 119.00   1.00    3.50    --  108.00  45.00 -60.00   26
 52  ω     90.00 116.00   1.00    3.50    --  108.00  61.00  90.00   26
;
_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      -0.0893482000
_diffrn_orient_matrix_UB_12      0.0064027000
_diffrn_orient_matrix_UB_13      -0.1314250000
_diffrn_orient_matrix_UB_21      0.1783894000
_diffrn_orient_matrix_UB_22      -0.0466653000
_diffrn_orient_matrix_UB_23      -0.0236454000
_diffrn_orient_matrix_UB_31      -0.0710215000
_diffrn_orient_matrix_UB_32      -0.1251655000
_diffrn_orient_matrix_UB_33      0.0021356000
_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         0.747
_reflns_Friedel_fraction_full    0.841
_reflns_Friedel_fraction_max     0.827
_reflns_number_gt                3241
_reflns_number_total             3515
_reflns_odcompleteness_completeness 99.95
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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         0.161
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1254 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(15)
_refine_ls_extinction_coef       0.0187(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.039
_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)+(0.0519P)²+0.0632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1013
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5C,H5D)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
C1 C 0.8141(3) 0.5681(2) 0.5721(2) 0.0426(6) Uani 1 1 d . . . . .
C2 C 1.0363(3) 0.4214(2) 0.6422(2) 0.0441(6) Uani 1 1 d . . . . .
C3 C 1.0517(3) 0.4629(2) 0.5193(2) 0.0467(6) Uani 1 1 d . . . . .
C4 C 1.2391(4) 0.5259(3) 0.5436(3) 0.0653(8) Uani 1 1 d . . . . .
H4A H 1.3277 0.4790 0.5177 0.078 Uiso 1 1 calc R . . . .
H4B H 1.2262 0.5999 0.5035 0.078 Uiso 1 1 calc R . . . .
C5 C 1.3008(4) 0.5440(4) 0.6728(3) 0.0722(9) Uani 1 1 d . . . . .
H5A H 1.2482 0.6144 0.6952 0.087 Uiso 1 1 calc R . . . .
H5B H 1.4337 0.5485 0.6994 0.087 Uiso 1 1 calc R . . . .
C6 C 1.2284(4) 0.4366(3) 0.7215(3) 0.0596(8) Uani 1 1 d . . . . .
H6A H 1.3044 0.3693 0.7183 0.072 Uiso 1 1 calc R . . . .
H6B H 1.2243 0.4490 0.8010 0.072 Uiso 1 1 calc R . . . .
C7 C 1.0331(5) 0.3670(3) 0.4303(3) 0.0644(8) Uani 1 1 d . . . . .
H7A H 0.9143 0.3314 0.4177 0.097 Uiso 1 1 calc GR . . . .
H7B H 1.1268 0.3097 0.4581 0.097 Uiso 1 1 calc GR . . . .
H7C H 1.0463 0.3990 0.3588 0.097 Uiso 1 1 calc GR . . . .
C8 C 0.8807(3) 0.5255(3) 0.7800(2) 0.0477(6) Uani 1 1 d . . . . .
C9 C 0.8571(5) 0.6375(3) 0.8151(3) 0.0648(8) Uani 1 1 d . . . . .
H9 H 0.8556 0.6995 0.7651 0.078 Uiso 1 1 calc R . . . .
C10 C 0.8355(6) 0.6570(4) 0.9253(4) 0.0800(11) Uani 1 1 d . . . . .
H10 H 0.8172 0.7324 0.9480 0.096 Uiso 1 1 calc R . . . .
C11 C 0.8408(5) 0.5675(4) 1.0013(3) 0.0774(11) Uani 1 1 d . . . . .
H11 H 0.8265 0.5816 1.0750 0.093 Uiso 1 1 calc R . . . .
C12 C 0.8675(5) 0.4569(4) 0.9670(3) 0.0751(10) Uani 1 1 d . . . . .
H12 H 0.8728 0.3956 1.0186 0.090 Uiso 1 1 calc R . . . .
C13 C 0.8865(5) 0.4347(3) 0.8574(3) 0.0621(8) Uani 1 1 d . . . . .
H13 H 0.9032 0.3590 0.8352 0.074 Uiso 1 1 calc R . . . .
C14 C 0.6631(4) 0.5426(3) 0.3143(2) 0.0494(6) Uani 1 1 d . . . . .
C15 C 0.4149(4) 0.5878(4) 0.1449(3) 0.0656(9) Uani 1 1 d . . . . .
C16 C 0.2825(5) 0.6104(5) 0.2186(3) 0.0890(13) Uani 1 1 d . . . . .
H16A H 0.2869 0.5467 0.2711 0.134 Uiso 1 1 calc GR . . . .
H16B H 0.1601 0.6180 0.1695 0.134 Uiso 1 1 calc GR . . . .
H16C H 0.3167 0.6807 0.2620 0.134 Uiso 1 1 calc GR . . . .
C17 C 0.3968(6) 0.4683(4) 0.0909(4) 0.0935(14) Uani 1 1 d . . . . .
H17A H 0.4956 0.4557 0.0553 0.140 Uiso 1 1 calc GR . . . .
H17B H 0.2815 0.4626 0.0334 0.140 Uiso 1 1 calc GR . . . .
H17C H 0.4019 0.4108 0.1498 0.140 Uiso 1 1 calc GR . . . .
C18 C 0.3995(6) 0.6806(5) 0.0540(4) 0.0929(14) Uani 1 1 d . . . . .
H18A H 0.4139 0.7556 0.0904 0.139 Uiso 1 1 calc GR . . . .
H18B H 0.2810 0.6760 -0.0005 0.139 Uiso 1 1 calc GR . . . .
H18C H 0.4937 0.6695 0.0143 0.139 Uiso 1 1 calc GR . . . .
N1 N 0.9036(3) 0.5046(2) 0.66745(19) 0.0440(5) Uani 1 1 d . . . . .
N2 N 0.8986(3) 0.5448(2) 0.48729(19) 0.0487(5) Uani 1 1 d . . . . .
N3 N 0.8287(3) 0.5853(2) 0.3762(2) 0.0492(5) Uani 1 1 d . . . . .
H3 H 0.868(4) 0.652(3) 0.356(3) 0.049(8) Uiso 1 1 d . . . . .
O1 O 0.6845(2) 0.63367(17) 0.56401(18) 0.0535(5) Uani 1 1 d . . . . .
O2 O 0.9753(2) 0.30649(17) 0.64678(18) 0.0510(5) Uani 1 1 d . . . . .
H2 H 0.8689 0.3008 0.6074 0.077 Uiso 1 1 calc GR . . . .
O3 O 0.5873(3) 0.4605(2) 0.3432(2) 0.0705(7) Uani 1 1 d . . . . .
O4 O 0.6049(3) 0.60494(19) 0.21818(16) 0.0553(5) Uani 1 1 d . . . . .
O5 O 0.6069(3) 0.3017(2) 0.5263(2) 0.0708(7) Uani 1 1 d . . . . .
H5C H 0.5971 0.3450 0.4673 0.106 Uiso 1 1 d G . . . .
H5D H 0.5371 0.2430 0.5075 0.106 Uiso 1 1 d G . . . .


_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
C1 N1 1.374(3) . ?
C1 N2 1.357(3) . ?
C1 O1 1.218(3) . ?
C2 C3 1.578(4) . ?
C2 C6 1.520(4) . ?
C2 N1 1.472(3) . ?
C2 O2 1.407(3) . ?
C3 C4 1.546(4) . ?
C3 C7 1.514(4) . ?
C3 N2 1.462(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.507(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.527(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.381(5) . ?
C8 C13 1.388(5) . ?
C8 N1 1.421(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.367(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(5) . ?
C13 H13 0.9300 . ?
C14 N3 1.366(4) . ?
C14 O3 1.200(4) . ?
C14 O4 1.329(3) . ?
C15 C16 1.516(5) . ?
C15 C17 1.511(6) . ?
C15 C18 1.506(6) . ?
C15 O4 1.484(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N2 N3 1.376(3) . ?
N3 H3 0.88(4) . ?
O2 H2 0.8200 . ?
O5 H5C 0.8503 . ?
O5 H5D 0.8497 . ?

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
N2 C1 N1 106.8(2) . . ?
O1 C1 N1 127.3(2) . . ?
O1 C1 N2 125.8(2) . . ?
C6 C2 C3 104.9(2) . . ?
N1 C2 C3 102.3(2) . . ?
N1 C2 C6 112.6(2) . . ?
O2 C2 C3 115.2(2) . . ?
O2 C2 C6 110.6(2) . . ?
O2 C2 N1 111.0(2) . . ?
C4 C3 C2 104.6(2) . . ?
C7 C3 C2 114.6(2) . . ?
C7 C3 C4 112.8(3) . . ?
N2 C3 C2 101.22(19) . . ?
N2 C3 C4 111.5(2) . . ?
N2 C3 C7 111.4(2) . . ?
C3 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C5 C4 C3 106.3(2) . . ?
C5 C4 H4A 110.5 . . ?
C5 C4 H4B 110.5 . . ?
C4 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
C4 C5 C6 103.5(3) . . ?
H5A C5 H5B 109.0 . . ?
C6 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
C2 C6 C5 103.4(2) . . ?
C2 C6 H6A 111.1 . . ?
C2 C6 H6B 111.1 . . ?
C5 C6 H6A 111.1 . . ?
C5 C6 H6B 111.1 . . ?
H6A C6 H6B 109.0 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 119.0(3) . . ?
C9 C8 N1 120.2(3) . . ?
C13 C8 N1 120.8(3) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
O3 C14 N3 124.4(3) . . ?
O3 C14 O4 126.8(3) . . ?
O4 C14 N3 108.8(2) . . ?
C17 C15 C16 113.8(4) . . ?
C18 C15 C16 111.0(4) . . ?
C18 C15 C17 110.9(3) . . ?
O4 C15 C16 108.3(3) . . ?
O4 C15 C17 109.8(3) . . ?
O4 C15 C18 102.3(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C2 112.9(2) . . ?
C1 N1 C8 122.7(2) . . ?
C8 N1 C2 124.1(2) . . ?
C1 N2 C3 115.1(2) . . ?
C1 N2 N3 121.2(2) . . ?
N3 N2 C3 123.3(2) . . ?
C14 N3 N2 117.8(2) . . ?
C14 N3 H3 120(2) . . ?
N2 N3 H3 119(2) . . ?
C2 O2 H2 109.5 . . ?
C14 O4 C15 119.3(2) . . ?
H5C O5 H5D 109.4 . . ?

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
N3 H3 O2 0.88(4) 2.14(4) 2.992(3) 163(3) 2_756
O2 H2 O5 0.82 1.96 2.775(3) 172.8 .
O5 H5C O3 0.85 1.98 2.826(3) 173.2 .
O5 H5D O1 0.85 2.09 2.915(3) 164.0 2_646

_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 1.266
_oxdiff_exptl_absorpt_empirical_full_min 0.851
