# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_210722f_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2fwp12
_database_code_depnum_ccdc_archive 'CCDC 2260924'
loop_
_audit_author_name
_audit_author_address
'Guanqun Zhan'
;Xian Jiaotong University
China
;
_audit_update_record             
;
2023-05-05 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_audit_creation_date             2023-04-26
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 N3 O3, C3 H6 O'
_chemical_formula_sum            'C24 H29 N3 O4'
_chemical_formula_weight         423.50
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   11.4154(14)
_cell_length_b                   8.0858(10)
_cell_length_c                   11.9564(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.308(2)
_cell_angle_gamma                90
_cell_volume                     1089.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9809
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.31
_cell_measurement_theta_min      4.76
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.935
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6837
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS, Madison WI for PHOTON III'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            35576
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         59.979
_diffrn_reflns_theta_min         6.435
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker Photon III 28 detector'
_diffrn_detector_area_resol_mean '7.39 for PHOTON III'
_diffrn_detector_type            'Bruker Photon III 28'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON III 28detector'
_diffrn_measurement_method       'Profile data from θ/2θ scans'
_diffrn_radiation_monochromator  'Metaljet Helios MX'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_xray_symbol    'Ga K\a'
_diffrn_source                   'METALJET liquid metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_target            Ga
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.926
_reflns_Friedel_fraction_max     0.844
_reflns_number_gt                4465
_reflns_number_total             4483
_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       
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_molecular_graphics    
'Bruker SHELXTL Bruker-AXS, Madison WI and local programs'
_computing_publication_material  'Bruker SHELXTL Bruker-AXS, Madison WI'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1900 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.12(15)
_refine_ls_extinction_coef       0.089(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4483
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.050
_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)+(0.0708P)²+0.2061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1061
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Ternary CH refined with riding coordinates: 
 C15(H15), C19(H19), C20(H20) 
2.b Secondary CH2 refined with riding coordinates: 
 C3(H3A,H3B), C14(H14A,H14B), C17(H17A,H17B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C9(H9), C10(H10), C11(H11), C12(H12), C23(H23), C24(H24), N1(H1) 
2.d Idealised Me refined as rotating group: 
 C18(H18A,H18B,H18C), C25(H25A,H25B,H25C), C1S(H1SA,H1SB,H1SC), C3S(H3SA,H3SB, 
 H3SC) 
2.e Idealised tetrahedral OH refined as rotating group: 
 O1(H1A) 
;
_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
C2 C 0.31203(16) 0.4814(2) 0.36699(15) 0.0202(4) Uani 1 1 d . . . . .
C3 C -0.09728(17) 0.5918(3) 0.16420(17) 0.0251(4) Uani 1 1 d . . . . .
H3A H -0.090873 0.518346 0.099202 0.030 Uiso 1 1 calc R U . . .
H3B H -0.181903 0.598858 0.172936 0.030 Uiso 1 1 calc R U . . .
C7 C 0.35443(16) 0.6132(2) 0.31444(15) 0.0195(4) Uani 1 1 d . . . . .
C8 C 0.48196(16) 0.6079(2) 0.34268(15) 0.0204(4) Uani 1 1 d . . . . .
C9 C 0.57482(17) 0.7026(3) 0.31279(16) 0.0224(4) Uani 1 1 d . . . . .
H9 H 0.558737 0.796456 0.265004 0.027 Uiso 1 1 calc R U . . .
C10 C 0.69132(17) 0.6564(3) 0.35455(17) 0.0251(4) Uani 1 1 d . . . . .
H10 H 0.754939 0.720710 0.335609 0.030 Uiso 1 1 calc R U . . .
C11 C 0.71662(17) 0.5164(3) 0.42417(17) 0.0259(4) Uani 1 1 d . . . . .
H11 H 0.796988 0.486693 0.449823 0.031 Uiso 1 1 calc R U . . .
C12 C 0.62664(17) 0.4208(3) 0.45616(17) 0.0254(4) Uani 1 1 d . . . . .
H12 H 0.643535 0.327075 0.503931 0.031 Uiso 1 1 calc R U . . .
C13 C 0.50991(17) 0.4688(3) 0.41488(16) 0.0216(4) Uani 1 1 d . . . . .
C14 C -0.02465(16) 0.5222(3) 0.27143(16) 0.0239(4) Uani 1 1 d . . . . .
H14A H -0.047943 0.406003 0.281773 0.029 Uiso 1 1 calc R U . . .
H14B H -0.040546 0.586659 0.337774 0.029 Uiso 1 1 calc R U . . .
C15 C 0.10808(15) 0.5304(2) 0.26375(16) 0.0198(4) Uani 1 1 d . . . . .
H15 H 0.118132 0.481698 0.189013 0.024 Uiso 1 1 calc R U . . .
C16 C 0.18572(16) 0.4255(2) 0.35751(16) 0.0202(4) Uani 1 1 d . . . . .
C17 C 0.17661(18) 0.2415(2) 0.32338(17) 0.0239(4) Uani 1 1 d . . . . .
H17A H 0.221850 0.173291 0.384348 0.029 Uiso 1 1 calc R U . . .
H17B H 0.092565 0.205817 0.312666 0.029 Uiso 1 1 calc R U . . .
C18 C 0.28847(17) 0.6990(3) 0.11333(16) 0.0259(4) Uani 1 1 d . . . . .
H18A H 0.266102 0.584466 0.093393 0.039 Uiso 1 1 calc R U . . .
H18B H 0.370798 0.717872 0.102833 0.039 Uiso 1 1 calc R U . . .
H18C H 0.235966 0.774502 0.064399 0.039 Uiso 1 1 calc R U . . .
C19 C 0.27676(15) 0.7308(2) 0.23778(15) 0.0196(4) Uani 1 1 d . . . . .
H19 H 0.304353 0.846051 0.257624 0.024 Uiso 1 1 calc R U . . .
C20 C 0.14866(16) 0.7129(2) 0.26315(15) 0.0192(4) Uani 1 1 d . . . . .
H20 H 0.148468 0.757454 0.341139 0.023 Uiso 1 1 calc R U . . .
C21 C 0.05962(17) 0.8122(2) 0.18359(15) 0.0206(4) Uani 1 1 d . . . . .
C22 C 0.13991(17) 0.4409(2) 0.47073(16) 0.0219(4) Uani 1 1 d . . . . .
C23 C -0.03313(19) 1.0079(3) 0.08300(17) 0.0271(4) Uani 1 1 d . . . . .
H23 H -0.049531 1.111623 0.046488 0.032 Uiso 1 1 calc R U . . .
C24 C -0.11146(18) 0.8813(3) 0.07950(17) 0.0279(4) Uani 1 1 d . . . . .
H24 H -0.190954 0.879019 0.040750 0.034 Uiso 1 1 calc R U . . .
C25 C 0.1541(2) 0.5885(3) 0.64239(18) 0.0304(4) Uani 1 1 d . . . . .
H25A H 0.067903 0.604763 0.630803 0.046 Uiso 1 1 calc R U . . .
H25B H 0.193540 0.686265 0.679619 0.046 Uiso 1 1 calc R U . . .
H25C H 0.174916 0.491064 0.690189 0.046 Uiso 1 1 calc R U . . .
N1 N 0.40490(14) 0.3940(2) 0.42862(14) 0.0223(4) Uani 1 1 d . . . . .
H1 H 0.397984 0.305366 0.469745 0.027 Uiso 1 1 calc R U . . .
N3 N 0.07440(15) 0.9641(2) 0.14761(14) 0.0249(4) Uani 1 1 d . . . . .
N4 N -0.05207(14) 0.7566(2) 0.14368(14) 0.0232(4) Uani 1 1 d . . . . .
O1 O 0.22267(13) 0.21829(19) 0.22160(13) 0.0272(3) Uani 1 1 d . . . . .
H1A H 0.182653 0.145891 0.182002 0.041 Uiso 1 1 calc R U . . .
O2 O 0.06494(13) 0.3516(2) 0.49937(13) 0.0286(4) Uani 1 1 d . . . . .
O3 O 0.19232(13) 0.56427(19) 0.53412(12) 0.0258(3) Uani 1 1 d . . . . .
C1S C 0.5949(3) 0.6056(5) 0.9869(3) 0.0532(7) Uani 1 1 d . . . . .
H1SA H 0.666923 0.581364 0.955041 0.080 Uiso 1 1 calc R U . . .
H1SB H 0.587352 0.525961 1.047112 0.080 Uiso 1 1 calc R U . . .
H1SC H 0.599896 0.717785 1.018280 0.080 Uiso 1 1 calc R U . . .
C2S C 0.4895(2) 0.5928(4) 0.8962(2) 0.0414(6) Uani 1 1 d . . . . .
C3S C 0.4846(3) 0.7085(7) 0.7995(4) 0.0903(17) Uani 1 1 d . . . . .
H3SA H 0.474422 0.821773 0.825533 0.135 Uiso 1 1 calc R U . . .
H3SB H 0.417488 0.679386 0.740811 0.135 Uiso 1 1 calc R U . . .
H3SC H 0.558577 0.701025 0.768101 0.135 Uiso 1 1 calc R U . . .
O1S O 0.4119(2) 0.4925(3) 0.89703(18) 0.0524(5) Uani 1 1 d . . . . .


_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
C2 C7 1.365(3) . ?
C2 C16 1.498(2) . ?
C2 N1 1.383(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C14 1.518(3) . ?
C3 N4 1.464(3) . ?
C7 C8 1.441(2) . ?
C7 C19 1.506(3) . ?
C8 C9 1.400(3) . ?
C8 C13 1.422(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.407(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.399(3) . ?
C13 N1 1.376(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.534(2) . ?
C15 H15 1.0000 . ?
C15 C16 1.562(3) . ?
C15 C20 1.547(3) . ?
C16 C17 1.542(3) . ?
C16 C22 1.533(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 O1 1.414(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C19 1.537(3) . ?
C19 H19 1.0000 . ?
C19 C20 1.548(2) . ?
C20 H20 1.0000 . ?
C20 C21 1.507(3) . ?
C21 N3 1.321(3) . ?
C21 N4 1.363(2) . ?
C22 O2 1.211(3) . ?
C22 O3 1.334(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.356(3) . ?
C23 N3 1.386(3) . ?
C24 H24 0.9500 . ?
C24 N4 1.377(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C25 O3 1.445(2) . ?
N1 H1 0.8800 . ?
O1 H1A 0.8400 . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C1S C2S 1.487(4) . ?
C2S C3S 1.481(5) . ?
C2S O1S 1.203(3) . ?
C3S H3SA 0.9800 . ?
C3S H3SB 0.9800 . ?
C3S H3SC 0.9800 . ?

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 C2 C16 127.54(18) . . ?
C7 C2 N1 110.23(17) . . ?
N1 C2 C16 122.13(17) . . ?
H3A C3 H3B 108.3 . . ?
C14 C3 H3A 110.0 . . ?
C14 C3 H3B 110.0 . . ?
N4 C3 H3A 110.0 . . ?
N4 C3 H3B 110.0 . . ?
N4 C3 C14 108.63(16) . . ?
C2 C7 C8 106.78(17) . . ?
C2 C7 C19 123.74(16) . . ?
C8 C7 C19 129.41(16) . . ?
C9 C8 C7 134.56(18) . . ?
C9 C8 C13 118.86(17) . . ?
C13 C8 C7 106.56(16) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.68(18) . . ?
C10 C9 H9 120.7 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.34(18) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.39(18) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 121.5 . . ?
C11 C12 C13 116.97(19) . . ?
C13 C12 H12 121.5 . . ?
C12 C13 C8 122.75(18) . . ?
N1 C13 C8 107.81(16) . . ?
N1 C13 C12 129.37(19) . . ?
C3 C14 H14A 109.6 . . ?
C3 C14 H14B 109.6 . . ?
C3 C14 C15 110.09(15) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C14 C15 H15 107.1 . . ?
C14 C15 C16 112.65(14) . . ?
C14 C15 C20 109.92(15) . . ?
C16 C15 H15 107.1 . . ?
C20 C15 H15 107.1 . . ?
C20 C15 C16 112.68(14) . . ?
C2 C16 C15 108.55(15) . . ?
C2 C16 C17 109.51(16) . . ?
C2 C16 C22 111.74(15) . . ?
C17 C16 C15 109.14(15) . . ?
C22 C16 C15 110.77(15) . . ?
C22 C16 C17 107.09(15) . . ?
C16 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
O1 C17 C16 109.69(15) . . ?
O1 C17 H17A 109.7 . . ?
O1 C17 H17B 109.7 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
C7 C19 C18 110.43(16) . . ?
C7 C19 H19 108.2 . . ?
C7 C19 C20 107.68(14) . . ?
C18 C19 H19 108.2 . . ?
C18 C19 C20 114.02(15) . . ?
C20 C19 H19 108.2 . . ?
C15 C20 C19 112.54(15) . . ?
C15 C20 H20 107.1 . . ?
C19 C20 H20 107.1 . . ?
C21 C20 C15 109.83(15) . . ?
C21 C20 C19 112.87(15) . . ?
C21 C20 H20 107.1 . . ?
N3 C21 C20 126.32(18) . . ?
N3 C21 N4 110.74(17) . . ?
N4 C21 C20 122.86(17) . . ?
O2 C22 C16 123.99(18) . . ?
O2 C22 O3 123.89(18) . . ?
O3 C22 C16 112.12(16) . . ?
C24 C23 H23 124.9 . . ?
C24 C23 N3 110.14(18) . . ?
N3 C23 H23 124.9 . . ?
C23 C24 H24 127.1 . . ?
C23 C24 N4 105.85(17) . . ?
N4 C24 H24 127.1 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
C2 N1 H1 125.7 . . ?
C13 N1 C2 108.62(16) . . ?
C13 N1 H1 125.7 . . ?
C21 N3 C23 105.71(18) . . ?
C21 N4 C3 125.21(16) . . ?
C21 N4 C24 107.56(17) . . ?
C24 N4 C3 127.21(17) . . ?
C17 O1 H1A 109.5 . . ?
C22 O3 C25 115.97(15) . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
C2S C1S H1SC 109.5 . . ?
C3S C2S C1S 116.7(3) . . ?
O1S C2S C1S 123.4(3) . . ?
O1S C2S C3S 119.8(3) . . ?
C2S C3S H3SA 109.5 . . ?
C2S C3S H3SB 109.5 . . ?
C2S C3S H3SC 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 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
_geom_hbond_publ_flag
O1 H1A N3 0.84 1.92 2.718(2) 157.8 1_545 yes

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
C2 C7 C8 C9 177.3(2) . . . . ?
C2 C7 C8 C13 -0.9(2) . . . . ?
C2 C7 C19 C18 -105.9(2) . . . . ?
C2 C7 C19 C20 19.1(2) . . . . ?
C2 C16 C17 O1 -56.1(2) . . . . ?
C2 C16 C22 O2 -150.05(19) . . . . ?
C2 C16 C22 O3 29.9(2) . . . . ?
C3 C14 C15 C16 -166.88(16) . . . . ?
C3 C14 C15 C20 66.6(2) . . . . ?
C7 C2 C16 C15 7.2(3) . . . . ?
C7 C2 C16 C17 126.3(2) . . . . ?
C7 C2 C16 C22 -115.3(2) . . . . ?
C7 C2 N1 C13 -0.8(2) . . . . ?
C7 C8 C9 C10 -177.7(2) . . . . ?
C7 C8 C13 C12 177.54(18) . . . . ?
C7 C8 C13 N1 0.4(2) . . . . ?
C7 C19 C20 C15 -49.28(19) . . . . ?
C7 C19 C20 C21 -174.29(14) . . . . ?
C8 C7 C19 C18 70.4(2) . . . . ?
C8 C7 C19 C20 -164.49(17) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C8 C13 N1 C2 0.2(2) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
C9 C8 C13 N1 -178.13(16) . . . . ?
C9 C10 C11 C12 -1.5(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C11 C12 C13 N1 176.9(2) . . . . ?
C12 C13 N1 C2 -176.7(2) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?
C14 C3 N4 C21 23.5(3) . . . . ?
C14 C3 N4 C24 -158.26(19) . . . . ?
C14 C15 C16 C2 -162.41(16) . . . . ?
C14 C15 C16 C17 78.29(19) . . . . ?
C14 C15 C16 C22 -39.4(2) . . . . ?
C14 C15 C20 C19 -171.52(15) . . . . ?
C14 C15 C20 C21 -44.86(19) . . . . ?
C15 C16 C17 O1 62.60(19) . . . . ?
C15 C16 C22 O2 88.8(2) . . . . ?
C15 C16 C22 O3 -91.23(18) . . . . ?
C15 C20 C21 N3 -168.03(18) . . . . ?
C15 C20 C21 N4 15.7(2) . . . . ?
C16 C2 C7 C8 -175.30(18) . . . . ?
C16 C2 C7 C19 1.8(3) . . . . ?
C16 C2 N1 C13 175.77(17) . . . . ?
C16 C15 C20 C19 61.95(19) . . . . ?
C16 C15 C20 C21 -171.39(15) . . . . ?
C16 C22 O3 C25 179.69(16) . . . . ?
C17 C16 C22 O2 -30.1(3) . . . . ?
C17 C16 C22 O3 149.87(16) . . . . ?
C18 C19 C20 C15 73.6(2) . . . . ?
C18 C19 C20 C21 -51.4(2) . . . . ?
C19 C7 C8 C9 0.5(3) . . . . ?
C19 C7 C8 C13 -177.72(18) . . . . ?
C19 C20 C21 N3 -41.6(3) . . . . ?
C19 C20 C21 N4 142.16(18) . . . . ?
C20 C15 C16 C2 -37.3(2) . . . . ?
C20 C15 C16 C17 -156.65(16) . . . . ?
C20 C15 C16 C22 85.69(18) . . . . ?
C20 C21 N3 C23 -175.95(18) . . . . ?
C20 C21 N4 C3 -5.2(3) . . . . ?
C20 C21 N4 C24 176.31(17) . . . . ?
C22 C16 C17 O1 -177.44(15) . . . . ?
C23 C24 N4 C3 -178.45(19) . . . . ?
C23 C24 N4 C21 0.0(2) . . . . ?
C24 C23 N3 C21 -0.7(2) . . . . ?
N1 C2 C7 C8 1.0(2) . . . . ?
N1 C2 C7 C19 178.11(16) . . . . ?
N1 C2 C16 C15 -168.74(17) . . . . ?
N1 C2 C16 C17 -49.7(2) . . . . ?
N1 C2 C16 C22 68.8(2) . . . . ?
N3 C21 N4 C3 178.04(17) . . . . ?
N3 C21 N4 C24 -0.5(2) . . . . ?
N3 C23 C24 N4 0.4(2) . . . . ?
N4 C3 C14 C15 -52.9(2) . . . . ?
N4 C21 N3 C23 0.7(2) . . . . ?
O2 C22 O3 C25 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
