# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 
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data_cu_22020375_0m
_database_code_depnum_ccdc_archive 'CCDC 2025858'
loop_
_audit_author_name
_audit_author_address
'Xiao-Bing Wang'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2020-08-28 deposited with the CCDC.	2021-01-25 downloaded from the CCDC.
;
_audit_creation_date             2020-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H25 F N2 O3'
_chemical_formula_sum            'C21 H25 F N2 O3'
_chemical_formula_weight         372.43
_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'
F F 0.0727 0.0534 '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                   10.4277(3)
_cell_length_b                   8.5846(2)
_cell_length_c                   22.3869(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.0440(10)
_cell_angle_gamma                90
_cell_volume                     1984.30(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9385
_cell_measurement_temperature    170
_cell_measurement_theta_max      72.428
_cell_measurement_theta_min      5.524
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1329 before and 0.0654 after correction. The Ratio of minimum to maximum transmission is 0.8585. 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    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17958
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        63.675
_diffrn_reflns_theta_max         63.675
_diffrn_reflns_theta_min         5.526
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2738
_reflns_number_total             3203
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     298
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.015
_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)+(0.0689P)²+0.5773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1354
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 O3-C19 \\sim O4-C19
 with sigma of 0.02
 O3-C22 \\sim O4-C23
 with sigma of 0.02
 C25-C22 \\sim C23-C24
 with sigma of 0.02
3. Rigid bond restraints
 C24, C23, C22, C25, O3, O4, O2, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Others
 Fixed Sof: H9AA(0.75) H9AB(0.75) H9BC(0.25) H9BD(0.25) H14A(0.75) H14B(0.75)
 H14C(0.25) H14D(0.25) H15A(0.75) H15B(0.75) H15C(0.75) H15D(0.25) H15E(0.25)
 H15F(0.25) O3(0.5) C12(0.75) H12A(0.75) H12B(0.75) C11(0.75) H11(0.75) O4(0.5)
 C13(0.25) H13A(0.25) H13B(0.25) C10(0.25) H10(0.25) C22(0.5) H22A(0.5)
 H22B(0.5) C25(0.5) H25A(0.5) H25B(0.5) H25C(0.5) C24(0.5) H24A(0.5) H24B(0.5)
 H24C(0.5) C23(0.5) H23A(0.5) H23B(0.5)
6.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9AA,H9AB), C9(H9BC,H9BD), C14(H14A,H14B), C14(H14C,H14D), C12(H12A,H12B),
 C13(H13A,H13B), C22(H22A,H22B), C23(H23A,H23B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C21(H21), C6(H6), C20(H20)
6.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C15(H15D,H15E,H15F), C17(H17A,H17B,
 H17C), C25(H25A,H25B,H25C), C24(H24A,H24B,H24C)
;
_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
F1 F 0.15666(11) 0.93442(14) 0.57909(5) 0.0664(4) Uani 1 1 d . U . . .
O1 O 0.40856(17) 0.53199(18) 0.32485(7) 0.0786(5) Uani 1 1 d . U . . .
N1 N 0.42303(14) 0.69042(16) 0.40807(6) 0.0486(4) Uani 1 1 d . U . . .
N2 N 0.37201(16) 0.7908(2) 0.31092(7) 0.0614(4) Uani 1 1 d . U . . .
C2 C 0.34884(17) 0.8430(2) 0.54804(8) 0.0497(4) Uani 1 1 d . U . . .
H2 H 0.394678 0.862117 0.587086 0.060 Uiso 1 1 calc R . . . .
C5 C 0.20480(17) 0.78286(19) 0.43195(8) 0.0480(4) Uani 1 1 d . U . . .
C7 C 0.54109(17) 0.73340(19) 0.49904(8) 0.0473(4) Uani 1 1 d . U . . .
C1 C 0.21963(18) 0.8743(2) 0.53455(8) 0.0516(4) Uani 1 1 d . U . . .
C4 C 0.33811(17) 0.75358(18) 0.44444(8) 0.0458(4) Uani 1 1 d . U . . .
C9 C 0.65732(18) 0.7385(2) 0.54629(9) 0.0540(5) Uani 1 1 d . U . . .
H9AA H 0.685468 0.847947 0.553112 0.065 Uiso 0.75 1 calc R . P A 1
H9AB H 0.633998 0.697344 0.584663 0.065 Uiso 0.75 1 calc R . P A 1
H9BC H 0.650628 0.655770 0.576522 0.065 Uiso 0.25 1 calc R . P B 2
H9BD H 0.661039 0.840277 0.567242 0.065 Uiso 0.25 1 calc R . P B 2
O2 O -0.01457(19) 0.6503(3) 0.26309(9) 0.1110(7) Uani 1 1 d . U . . .
C21 C 0.12786(18) 0.7428(2) 0.37452(9) 0.0540(5) Uani 1 1 d . U . . .
H21 H 0.160213 0.661376 0.352050 0.065 Uiso 1 1 calc R . . . .
C3 C 0.41074(16) 0.78123(19) 0.50156(8) 0.0458(4) Uani 1 1 d . U . . .
C6 C 0.14720(17) 0.8472(2) 0.47919(8) 0.0515(4) Uani 1 1 d . U . . .
H6 H 0.057604 0.872381 0.473022 0.062 Uiso 1 1 calc R . . . .
C18 C 0.40019(18) 0.6625(2) 0.34437(9) 0.0540(5) Uani 1 1 d . U . . .
C8 C 0.54505(17) 0.67897(19) 0.44227(8) 0.0484(4) Uani 1 1 d . U . . .
C14 C 0.66281(18) 0.6203(2) 0.41872(9) 0.0572(5) Uani 1 1 d . U . . .
H14A H 0.668332 0.665927 0.378541 0.069 Uiso 0.75 1 calc R . P C 1
H14B H 0.658890 0.505556 0.414624 0.069 Uiso 0.75 1 calc R . P C 1
H14C H 0.694774 0.701698 0.393146 0.069 Uiso 0.25 1 calc R . P D 2
H14D H 0.639379 0.527848 0.393095 0.069 Uiso 0.25 1 calc R . P D 2
C20 C 0.0182(2) 0.8077(3) 0.35059(10) 0.0690(6) Uani 1 1 d . U . . .
H20 H -0.017238 0.891308 0.370762 0.083 Uiso 1 1 calc R . . . .
C16 C 0.3783(2) 0.9493(3) 0.33491(11) 0.0748(6) Uani 1 1 d . U . . .
H16A H 0.290584 0.985855 0.338417 0.112 Uiso 1 1 calc GR . . . .
H16B H 0.417565 1.018156 0.307619 0.112 Uiso 1 1 calc GR . . . .
H16C H 0.430817 0.950310 0.374784 0.112 Uiso 1 1 calc GR . . . .
C15 C 0.8936(2) 0.6743(3) 0.56946(11) 0.0725(6) Uani 1 1 d . U . . .
H15A H 0.914839 0.785452 0.569323 0.109 Uiso 0.75 1 calc GR . P E 1
H15B H 0.962669 0.614294 0.554669 0.109 Uiso 0.75 1 calc GR . P E 1
H15C H 0.885201 0.641400 0.610657 0.109 Uiso 0.75 1 calc GR . P E 1
H15D H 0.889664 0.749868 0.601954 0.109 Uiso 0.25 1 calc GR . P F 2
H15E H 0.979170 0.678745 0.556191 0.109 Uiso 0.25 1 calc GR . P F 2
H15F H 0.878602 0.569286 0.584233 0.109 Uiso 0.25 1 calc GR . P F 2
O3 O -0.1418(5) 0.8611(8) 0.2688(2) 0.0909(16) Uani 0.5 1 d D U P G 2
C17 C 0.3264(3) 0.7748(4) 0.24656(10) 0.0880(8) Uani 1 1 d . U . . .
H17A H 0.344231 0.668994 0.233484 0.132 Uiso 1 1 calc GR . . . .
H17B H 0.371437 0.850155 0.223998 0.132 Uiso 1 1 calc GR . . . .
H17C H 0.232985 0.794466 0.238986 0.132 Uiso 1 1 calc GR . . . .
C12 C 0.7806(3) 0.6674(4) 0.46308(14) 0.0599(7) Uani 0.75 1 d . U P H 1
H12A H 0.855933 0.605601 0.454312 0.072 Uiso 0.75 1 calc R . P H 1
H12B H 0.799918 0.778411 0.456330 0.072 Uiso 0.75 1 calc R . P H 1
C19 C -0.0494(2) 0.7509(4) 0.29277(12) 0.0856(8) Uani 1 1 d D U . . .
C11 C 0.7658(3) 0.6457(4) 0.52851(15) 0.0595(8) Uani 0.75 1 d . U P H 1
H11 H 0.743266 0.533638 0.533526 0.071 Uiso 0.75 1 calc R . P H 1
O4 O -0.1755(5) 0.7995(6) 0.2839(2) 0.0880(14) Uani 0.5 1 d D U P G 1
C13 C 0.7717(7) 0.5762(9) 0.4694(4) 0.053(2) Uani 0.25 1 d . U P H 2
H13A H 0.853502 0.558723 0.452654 0.064 Uiso 0.25 1 calc R . P H 2
H13B H 0.749156 0.479162 0.489458 0.064 Uiso 0.25 1 calc R . P H 2
C10 C 0.7886(8) 0.7135(10) 0.5159(4) 0.047(2) Uani 0.25 1 d . U P H 2
H10 H 0.811455 0.811580 0.495762 0.057 Uiso 0.25 1 calc R . P H 2
C22 C -0.2159(6) 0.8054(16) 0.2130(3) 0.110(3) Uani 0.5 1 d D U P G 2
H22A H -0.211746 0.884786 0.181232 0.132 Uiso 0.5 1 calc R . P G 2
H22B H -0.174545 0.709422 0.200311 0.132 Uiso 0.5 1 calc R . P G 2
C25 C -0.3500(7) 0.7726(13) 0.2171(4) 0.123(3) Uani 0.5 1 d D U P G 2
H25A H -0.398469 0.764959 0.176407 0.185 Uiso 0.5 1 calc GR . P G 2
H25B H -0.386147 0.856620 0.239197 0.185 Uiso 0.5 1 calc GR . P G 2
H25C H -0.356393 0.673806 0.238409 0.185 Uiso 0.5 1 calc GR . P G 2
C24 C -0.2714(19) 0.8576(12) 0.1902(3) 0.191(6) Uani 0.5 1 d D U P G 1
H24A H -0.301445 0.954652 0.206620 0.287 Uiso 0.5 1 calc GR . P G 1
H24B H -0.329937 0.828747 0.153709 0.287 Uiso 0.5 1 calc GR . P G 1
H24C H -0.183755 0.872459 0.180079 0.287 Uiso 0.5 1 calc GR . P G 1
C23 C -0.2702(15) 0.7434(11) 0.2315(4) 0.130(3) Uani 0.5 1 d D U P G 1
H23A H -0.241164 0.643661 0.215659 0.157 Uiso 0.5 1 calc R . P G 1
H23B H -0.357249 0.728708 0.243455 0.157 Uiso 0.5 1 calc R . P G 1


_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
F1 C1 1.3695(19) . ?
O1 C18 1.210(2) . ?
N1 C4 1.394(2) . ?
N1 C18 1.433(2) . ?
N1 C8 1.394(2) . ?
N2 C18 1.341(3) . ?
N2 C16 1.461(3) . ?
N2 C17 1.459(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.366(3) . ?
C2 C3 1.403(2) . ?
C5 C4 1.402(3) . ?
C5 C21 1.458(3) . ?
C5 C6 1.401(2) . ?
C7 C9 1.494(3) . ?
C7 C3 1.429(2) . ?
C7 C8 1.360(3) . ?
C1 C6 1.378(3) . ?
C4 C3 1.412(2) . ?
C9 H9AA 0.9900 . ?
C9 H9AB 0.9900 . ?
C9 H9BC 0.9900 . ?
C9 H9BD 0.9900 . ?
C9 C11 1.483(4) . ?
C9 C10 1.625(9) . ?
O2 C19 1.177(3) . ?
C21 H21 0.9500 . ?
C21 C20 1.317(3) . ?
C6 H6 0.9500 . ?
C8 C14 1.490(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 H14C 0.9900 . ?
C14 H14D 0.9900 . ?
C14 C12 1.522(4) . ?
C14 C13 1.537(8) . ?
C20 H20 0.9500 . ?
C20 C19 1.468(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 H15D 0.9800 . ?
C15 H15E 0.9800 . ?
C15 H15F 0.9800 . ?
C15 C11 1.528(4) . ?
C15 C10 1.544(9) . ?
O3 C19 1.403(6) . ?
O3 C22 1.454(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.506(5) . ?
C19 O4 1.367(6) . ?
C11 H11 1.0000 . ?
O4 C23 1.502(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C10 1.566(13) . ?
C10 H10 1.0000 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C25 1.442(10) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 C23 1.347(10) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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
C4 N1 C18 128.01(15) . . ?
C8 N1 C4 108.19(14) . . ?
C8 N1 C18 123.16(14) . . ?
C18 N2 C16 124.38(17) . . ?
C18 N2 C17 119.30(19) . . ?
C17 N2 C16 116.3(2) . . ?
C1 C2 H2 121.6 . . ?
C1 C2 C3 116.89(16) . . ?
C3 C2 H2 121.6 . . ?
C4 C5 C21 122.79(16) . . ?
C6 C5 C4 115.98(16) . . ?
C6 C5 C21 121.17(16) . . ?
C3 C7 C9 130.23(16) . . ?
C8 C7 C9 122.96(16) . . ?
C8 C7 C3 106.81(16) . . ?
F1 C1 C6 117.40(16) . . ?
C2 C1 F1 118.15(16) . . ?
C2 C1 C6 124.44(16) . . ?
N1 C4 C5 130.28(16) . . ?
N1 C4 C3 106.88(15) . . ?
C5 C4 C3 122.81(16) . . ?
C7 C9 H9AA 109.3 . . ?
C7 C9 H9AB 109.3 . . ?
C7 C9 H9BC 109.6 . . ?
C7 C9 H9BD 109.6 . . ?
C7 C9 C10 110.3(4) . . ?
H9AA C9 H9AB 108.0 . . ?
H9BC C9 H9BD 108.1 . . ?
C11 C9 C7 111.60(19) . . ?
C11 C9 H9AA 109.3 . . ?
C11 C9 H9AB 109.3 . . ?
C10 C9 H9BC 109.6 . . ?
C10 C9 H9BD 109.6 . . ?
C5 C21 H21 116.6 . . ?
C20 C21 C5 126.74(18) . . ?
C20 C21 H21 116.6 . . ?
C2 C3 C7 132.60(17) . . ?
C2 C3 C4 119.41(16) . . ?
C4 C3 C7 107.98(15) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 C5 120.43(17) . . ?
C1 C6 H6 119.8 . . ?
O1 C18 N1 120.25(18) . . ?
O1 C18 N2 125.45(19) . . ?
N2 C18 N1 114.29(16) . . ?
N1 C8 C14 124.30(16) . . ?
C7 C8 N1 110.15(15) . . ?
C7 C8 C14 125.52(17) . . ?
C8 C14 H14A 110.1 . . ?
C8 C14 H14B 110.1 . . ?
C8 C14 H14C 109.1 . . ?
C8 C14 H14D 109.1 . . ?
C8 C14 C12 108.01(17) . . ?
C8 C14 C13 112.5(3) . . ?
H14A C14 H14B 108.4 . . ?
H14C C14 H14D 107.8 . . ?
C12 C14 H14A 110.1 . . ?
C12 C14 H14B 110.1 . . ?
C13 C14 H14C 109.1 . . ?
C13 C14 H14D 109.1 . . ?
C21 C20 H20 120.0 . . ?
C21 C20 C19 120.1(2) . . ?
C19 C20 H20 120.0 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H15D C15 H15E 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
C10 C15 H15D 109.5 . . ?
C10 C15 H15E 109.5 . . ?
C10 C15 H15F 109.5 . . ?
C19 O3 C22 111.2(7) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C12 H12A 108.6 . . ?
C14 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C11 C12 C14 114.7(2) . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
O2 C19 C20 126.4(2) . . ?
O2 C19 O3 121.9(3) . . ?
O2 C19 O4 120.6(3) . . ?
O3 C19 C20 109.5(3) . . ?
O4 C19 C20 111.1(3) . . ?
C9 C11 C15 112.7(3) . . ?
C9 C11 C12 112.4(3) . . ?
C9 C11 H11 106.6 . . ?
C15 C11 H11 106.6 . . ?
C12 C11 C15 111.4(3) . . ?
C12 C11 H11 106.6 . . ?
C19 O4 C23 121.9(7) . . ?
C14 C13 H13A 110.1 . . ?
C14 C13 H13B 110.1 . . ?
C14 C13 C10 107.9(6) . . ?
H13A C13 H13B 108.4 . . ?
C10 C13 H13A 110.1 . . ?
C10 C13 H13B 110.1 . . ?
C9 C10 H10 110.2 . . ?
C15 C10 C9 104.6(6) . . ?
C15 C10 C13 110.7(6) . . ?
C15 C10 H10 110.2 . . ?
C13 C10 C9 110.8(6) . . ?
C13 C10 H10 110.2 . . ?
O3 C22 H22A 108.7 . . ?
O3 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C25 C22 O3 114.4(6) . . ?
C25 C22 H22A 108.7 . . ?
C25 C22 H22B 108.7 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
O4 C23 H23A 110.9 . . ?
O4 C23 H23B 110.9 . . ?
C24 C23 O4 104.2(9) . . ?
C24 C23 H23A 110.9 . . ?
C24 C23 H23B 110.9 . . ?
H23A C23 H23B 108.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
