# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
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data_cu_230519_ch_3ka_0m
_database_code_depnum_ccdc_archive 'CCDC 2264258'
loop_
_audit_author_name
_audit_author_address
'Hong Chen'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2023-05-20 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_audit_creation_date             2023-05-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H33 N O4'
_chemical_formula_sum            'C25 H33 N O4'
_chemical_formula_weight         411.52
_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 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.82470(10)
_cell_length_b                   15.1975(3)
_cell_length_c                   20.6745(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2144.33(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      74.58
_cell_measurement_theta_min      3.61
_shelx_estimated_absorpt_T_max   0.876
_shelx_estimated_absorpt_T_min   0.735
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1409 before and 0.0806 after correction.
The Ratio of minimum to maximum transmission is 0.7518.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22064
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.568
_diffrn_reflns_theta_min         3.609
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4025
_reflns_number_total             4363
_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 Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1620 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4363
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.032
_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)+(0.0628P)²+0.2586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1077
_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
2. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C11(H11), C13(H13), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C10(H10A,H10B), C12(H12A,
 H12B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C23(H23), C24(H24)
3.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.6185(3) 0.35376(14) 0.54347(11) 0.0414(5) Uani 1 1 d . . . . .
O2 O 0.6052(3) 0.53810(13) 0.47821(8) 0.0343(4) Uani 1 1 d . . . . .
O3 O 0.4854(2) 0.56605(11) 0.57857(8) 0.0278(3) Uani 1 1 d . . . . .
O4 O -0.0764(3) 0.56496(14) 0.23805(9) 0.0380(4) Uani 1 1 d . . . . .
N1 N 0.3115(3) 0.42130(14) 0.45161(10) 0.0302(4) Uani 1 1 d D . . . .
C1 C 0.4722(3) 0.33899(16) 0.57448(12) 0.0276(5) Uani 1 1 d . . . . .
C2 C 0.4586(4) 0.26217(18) 0.62041(13) 0.0357(6) Uani 1 1 d . . . . .
H2A H 0.470800 0.284048 0.665334 0.043 Uiso 1 1 calc R U . . .
H2B H 0.569523 0.221711 0.612183 0.043 Uiso 1 1 calc R U . . .
C3 C 0.2669(4) 0.21127(17) 0.61387(14) 0.0358(5) Uani 1 1 d . . . . .
H3A H 0.258432 0.166394 0.648470 0.043 Uiso 1 1 calc R U . . .
H3B H 0.263827 0.180563 0.571652 0.043 Uiso 1 1 calc R U . . .
C4 C 0.0922(4) 0.27388(18) 0.61878(14) 0.0373(6) Uani 1 1 d . . . . .
H4A H -0.031154 0.240214 0.614170 0.045 Uiso 1 1 calc R U . . .
H4B H 0.091840 0.302503 0.661790 0.045 Uiso 1 1 calc R U . . .
C5 C 0.1036(4) 0.34394(17) 0.56605(14) 0.0351(5) Uani 1 1 d . . . . .
H5A H -0.010511 0.383782 0.569976 0.042 Uiso 1 1 calc R U . . .
H5B H 0.096741 0.315087 0.523178 0.042 Uiso 1 1 calc R U . . .
C6 C 0.2933(3) 0.39846(14) 0.57019(11) 0.0257(4) Uani 1 1 d . . . . .
H6 H 0.287324 0.432979 0.611314 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3101(3) 0.46499(15) 0.51448(11) 0.0264(4) Uani 1 1 d . . . . .
H7 H 0.190277 0.502783 0.515969 0.032 Uiso 1 1 calc R U . . .
C8 C 0.4873(3) 0.52629(15) 0.52038(11) 0.0266(4) Uani 1 1 d . . . . .
C9 C 0.6514(3) 0.62065(15) 0.60027(11) 0.0242(4) Uani 1 1 d . . . . .
C10 C 0.8341(3) 0.56367(15) 0.60708(11) 0.0275(5) Uani 1 1 d . . . . .
H10A H 0.874883 0.541286 0.564173 0.033 Uiso 1 1 calc R U . . .
H10B H 0.806266 0.512670 0.635416 0.033 Uiso 1 1 calc R U . . .
C11 C 0.9989(4) 0.62020(17) 0.63665(12) 0.0304(5) Uani 1 1 d . . . . .
H11 H 1.120043 0.583714 0.641286 0.036 Uiso 1 1 calc R U . . .
C12 C 0.9347(4) 0.65334(19) 0.70344(12) 0.0351(5) Uani 1 1 d . . . . .
H12A H 0.906299 0.602718 0.732093 0.042 Uiso 1 1 calc R U . . .
H12B H 1.041196 0.688359 0.723278 0.042 Uiso 1 1 calc R U . . .
C13 C 0.7510(4) 0.71026(18) 0.69598(12) 0.0341(5) Uani 1 1 d . . . . .
H13 H 0.709170 0.732515 0.739357 0.041 Uiso 1 1 calc R U . . .
C14 C 0.5858(4) 0.65402(17) 0.66645(11) 0.0294(5) Uani 1 1 d . . . . .
H14A H 0.556309 0.603611 0.695171 0.035 Uiso 1 1 calc R U . . .
H14B H 0.465396 0.689823 0.661865 0.035 Uiso 1 1 calc R U . . .
C15 C 0.6903(4) 0.69876(15) 0.55526(12) 0.0277(5) Uani 1 1 d . . . . .
H15A H 0.570106 0.734687 0.550615 0.033 Uiso 1 1 calc R U . . .
H15B H 0.729267 0.677401 0.511893 0.033 Uiso 1 1 calc R U . . .
C16 C 0.8560(4) 0.75462(16) 0.58483(13) 0.0320(5) Uani 1 1 d . . . . .
H16 H 0.884281 0.805772 0.555866 0.038 Uiso 1 1 calc R U . . .
C17 C 0.7949(4) 0.78822(17) 0.65139(14) 0.0369(6) Uani 1 1 d . . . . .
H17A H 0.676935 0.825700 0.647285 0.044 Uiso 1 1 calc R U . . .
H17B H 0.901522 0.824324 0.670112 0.044 Uiso 1 1 calc R U . . .
C18 C 1.0407(4) 0.69791(17) 0.59155(13) 0.0332(5) Uani 1 1 d . . . . .
H18A H 1.081141 0.675850 0.548519 0.040 Uiso 1 1 calc R U . . .
H18B H 1.149061 0.733819 0.609357 0.040 Uiso 1 1 calc R U . . .
C19 C 0.2094(3) 0.45986(15) 0.39972(12) 0.0275(4) Uani 1 1 d . . . . .
C20 C 0.0205(4) 0.49324(16) 0.40616(12) 0.0300(5) Uani 1 1 d . . . . .
H20 H -0.041030 0.492056 0.447372 0.036 Uiso 1 1 calc R U . . .
C21 C -0.0804(3) 0.52835(17) 0.35360(12) 0.0298(5) Uani 1 1 d . . . . .
H21 H -0.208905 0.551187 0.359144 0.036 Uiso 1 1 calc R U . . .
C22 C 0.0076(4) 0.52983(16) 0.29310(12) 0.0295(5) Uani 1 1 d . . . . .
C23 C 0.1936(4) 0.49402(17) 0.28520(12) 0.0323(5) Uani 1 1 d . . . . .
H23 H 0.252433 0.492679 0.243566 0.039 Uiso 1 1 calc R U . . .
C24 C 0.2929(4) 0.46037(16) 0.33800(12) 0.0310(5) Uani 1 1 d . . . . .
H24 H 0.420801 0.437063 0.332180 0.037 Uiso 1 1 calc R U . . .
C25 C -0.2535(4) 0.6115(2) 0.24618(15) 0.0423(6) Uani 1 1 d . . . . .
H25A H -0.291709 0.638382 0.204966 0.063 Uiso 1 1 calc R U . . .
H25B H -0.235472 0.657661 0.278765 0.063 Uiso 1 1 calc R U . . .
H25C H -0.356317 0.570927 0.260447 0.063 Uiso 1 1 calc R U . . .
H1 H 0.432(4) 0.409(3) 0.4400(18) 0.051 Uiso 1 1 d D U . . .


_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 1.207(3) . ?
O2 C8 1.200(3) . ?
O3 C8 1.346(3) . ?
O3 C9 1.474(3) . ?
O4 C22 1.382(3) . ?
O4 C25 1.411(3) . ?
N1 C7 1.460(3) . ?
N1 C19 1.407(3) . ?
N1 H1 0.88(2) . ?
C1 C2 1.508(3) . ?
C1 C6 1.521(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.526(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.529(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.526(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.539(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.537(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.531(3) . ?
C9 C10 1.525(3) . ?
C9 C14 1.526(3) . ?
C9 C15 1.531(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.541(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.534(3) . ?
C11 C18 1.531(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.531(4) . ?
C13 H13 1.0000 . ?
C13 C14 1.541(3) . ?
C13 C17 1.531(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.541(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.526(4) . ?
C16 C18 1.533(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.392(3) . ?
C19 C24 1.398(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.393(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(3) . ?
C22 C23 1.391(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.383(4) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C8 O3 C9 121.16(18) . . ?
C22 O4 C25 116.8(2) . . ?
C7 N1 H1 110(3) . . ?
C19 N1 C7 119.10(19) . . ?
C19 N1 H1 110(3) . . ?
O1 C1 C2 122.0(2) . . ?
O1 C1 C6 121.5(2) . . ?
C2 C1 C6 116.6(2) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 C3 112.9(2) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C2 C3 C4 110.3(2) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.3(2) . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C4 C5 C6 112.3(2) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C1 C6 C5 111.00(18) . . ?
C1 C6 H6 107.2 . . ?
C1 C6 C7 112.01(19) . . ?
C5 C6 H6 107.2 . . ?
C7 C6 C5 112.0(2) . . ?
C7 C6 H6 107.2 . . ?
N1 C7 C6 111.62(19) . . ?
N1 C7 H7 107.1 . . ?
N1 C7 C8 110.04(19) . . ?
C6 C7 H7 107.1 . . ?
C8 C7 C6 113.55(18) . . ?
C8 C7 H7 107.1 . . ?
O2 C8 O3 126.0(2) . . ?
O2 C8 C7 124.2(2) . . ?
O3 C8 C7 109.68(19) . . ?
O3 C9 C10 109.69(17) . . ?
O3 C9 C14 103.57(17) . . ?
O3 C9 C15 112.63(18) . . ?
C10 C9 C14 110.22(19) . . ?
C10 C9 C15 110.75(18) . . ?
C14 C9 C15 109.75(19) . . ?
C9 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
C9 C10 C11 108.48(18) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
C10 C11 H11 109.4 . . ?
C12 C11 C10 109.4(2) . . ?
C12 C11 H11 109.4 . . ?
C18 C11 C10 108.92(19) . . ?
C18 C11 H11 109.4 . . ?
C18 C11 C12 110.4(2) . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 C11 109.2(2) . . ?
C13 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C12 C13 H13 109.5 . . ?
C12 C13 C14 109.0(2) . . ?
C14 C13 H13 109.5 . . ?
C17 C13 C12 109.7(2) . . ?
C17 C13 H13 109.5 . . ?
C17 C13 C14 109.5(2) . . ?
C9 C14 C13 108.97(19) . . ?
C9 C14 H14A 109.9 . . ?
C9 C14 H14B 109.9 . . ?
C13 C14 H14A 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C9 C15 H15A 110.0 . . ?
C9 C15 H15B 110.0 . . ?
C9 C15 C16 108.27(19) . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 H15A 110.0 . . ?
C16 C15 H15B 110.0 . . ?
C15 C16 H16 109.4 . . ?
C17 C16 C15 110.0(2) . . ?
C17 C16 H16 109.4 . . ?
C17 C16 C18 109.3(2) . . ?
C18 C16 C15 109.3(2) . . ?
C18 C16 H16 109.4 . . ?
C13 C17 H17A 109.7 . . ?
C13 C17 H17B 109.7 . . ?
C16 C17 C13 109.7(2) . . ?
C16 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C11 C18 C16 109.6(2) . . ?
C11 C18 H18A 109.7 . . ?
C11 C18 H18B 109.7 . . ?
C16 C18 H18A 109.7 . . ?
C16 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C20 C19 N1 122.5(2) . . ?
C20 C19 C24 117.6(2) . . ?
C24 C19 N1 119.8(2) . . ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.5(2) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.7(2) . . ?
C22 C21 H21 120.1 . . ?
O4 C22 C21 124.7(2) . . ?
O4 C22 C23 115.7(2) . . ?
C21 C22 C23 119.6(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 119.9(2) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 119.2 . . ?
C23 C24 C19 121.5(2) . . ?
C23 C24 H24 119.2 . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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 C2 C3 -134.7(3) . . . . ?
O1 C1 C6 C5 136.6(3) . . . . ?
O1 C1 C6 C7 10.6(3) . . . . ?
O3 C9 C10 C11 -174.07(17) . . . . ?
O3 C9 C14 C13 178.12(19) . . . . ?
O3 C9 C15 C16 176.10(18) . . . . ?
O4 C22 C23 C24 177.5(2) . . . . ?
N1 C7 C8 O2 2.2(3) . . . . ?
N1 C7 C8 O3 -179.75(19) . . . . ?
N1 C19 C20 C21 -177.7(2) . . . . ?
N1 C19 C24 C23 177.0(2) . . . . ?
C1 C2 C3 C4 -52.4(3) . . . . ?
C1 C6 C7 N1 65.2(2) . . . . ?
C1 C6 C7 C8 -59.9(2) . . . . ?
C2 C1 C6 C5 -44.7(3) . . . . ?
C2 C1 C6 C7 -170.7(2) . . . . ?
C2 C3 C4 C5 58.9(3) . . . . ?
C3 C4 C5 C6 -58.9(3) . . . . ?
C4 C5 C6 C1 50.4(3) . . . . ?
C4 C5 C6 C7 176.4(2) . . . . ?
C5 C6 C7 N1 -60.3(2) . . . . ?
C5 C6 C7 C8 174.62(19) . . . . ?
C6 C1 C2 C3 46.6(3) . . . . ?
C6 C7 C8 O2 128.1(2) . . . . ?
C6 C7 C8 O3 -53.8(2) . . . . ?
C7 N1 C19 C20 -45.3(3) . . . . ?
C7 N1 C19 C24 138.9(2) . . . . ?
C8 O3 C9 C10 -63.9(3) . . . . ?
C8 O3 C9 C14 178.4(2) . . . . ?
C8 O3 C9 C15 59.9(3) . . . . ?
C9 O3 C8 O2 -9.3(4) . . . . ?
C9 O3 C8 C7 172.71(18) . . . . ?
C9 C10 C11 C12 60.4(2) . . . . ?
C9 C10 C11 C18 -60.3(2) . . . . ?
C9 C15 C16 C17 -60.2(2) . . . . ?
C9 C15 C16 C18 59.8(3) . . . . ?
C10 C9 C14 C13 60.8(3) . . . . ?
C10 C9 C15 C16 -60.6(2) . . . . ?
C10 C11 C12 C13 -61.0(3) . . . . ?
C10 C11 C18 C16 61.1(3) . . . . ?
C11 C12 C13 C14 60.7(3) . . . . ?
C11 C12 C13 C17 -59.2(3) . . . . ?
C12 C11 C18 C16 -59.0(3) . . . . ?
C12 C13 C14 C9 -60.3(3) . . . . ?
C12 C13 C17 C16 60.5(3) . . . . ?
C14 C9 C10 C11 -60.6(2) . . . . ?
C14 C9 C15 C16 61.3(2) . . . . ?
C14 C13 C17 C16 -59.1(3) . . . . ?
C15 C9 C10 C11 61.0(2) . . . . ?
C15 C9 C14 C13 -61.4(2) . . . . ?
C15 C16 C17 C13 59.7(3) . . . . ?
C15 C16 C18 C11 -61.0(3) . . . . ?
C17 C13 C14 C9 59.8(3) . . . . ?
C17 C16 C18 C11 59.4(3) . . . . ?
C18 C11 C12 C13 58.8(3) . . . . ?
C18 C16 C17 C13 -60.3(3) . . . . ?
C19 N1 C7 C6 140.8(2) . . . . ?
C19 N1 C7 C8 -92.2(2) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C20 C19 C24 C23 1.0(4) . . . . ?
C20 C21 C22 O4 -178.3(2) . . . . ?
C20 C21 C22 C23 1.8(4) . . . . ?
C21 C22 C23 C24 -2.5(4) . . . . ?
C22 C23 C24 C19 1.1(4) . . . . ?
C24 C19 C20 C21 -1.8(3) . . . . ?
C25 O4 C22 C21 7.8(4) . . . . ?
C25 O4 C22 C23 -172.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
