# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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. 
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data_mo_0428_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2101084'
loop_
_audit_author_name
_audit_author_address
'gang wang'
;Xinjiang University
China
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_audit_creation_date             2021-04-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H13 F2 N O'
_chemical_formula_sum            'C22 H13 F2 N O'
_chemical_formula_weight         345.33
_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 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.1916(17)
_cell_length_b                   9.9649(5)
_cell_length_c                   14.5436(11)
_cell_angle_alpha                90
_cell_angle_beta                 112.784(3)
_cell_angle_gamma                90
_cell_volume                     3232.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3725
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      25.92
_cell_measurement_theta_min      3.04
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0789 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.4130.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_colour_primary    .
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.2
_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  0.0705
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28476
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.465
_diffrn_reflns_theta_min         2.238
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2614
_reflns_number_total             3311
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.105
_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)+(0.0493P)²+1.6768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00C(H00C), C00D(H00D), C00E(H00E), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F001 F 0.26037(5) 0.48710(10) 0.60648(8) 0.0423(3) Uani 1 1 d . . . . .
F002 F 0.20357(4) 0.45210(10) 0.45219(8) 0.0448(3) Uani 1 1 d . . . . .
O003 O 0.43260(5) 0.06059(11) 0.56578(10) 0.0414(3) Uani 1 1 d . . . . .
N004 N 0.39271(6) 0.27434(13) 0.52970(10) 0.0318(3) Uani 1 1 d . . . . .
C005 C 0.30167(7) 0.33376(16) 0.40821(13) 0.0332(4) Uani 1 1 d . . . . .
C006 C 0.40472(7) 0.51164(15) 0.58819(12) 0.0309(3) Uani 1 1 d . . . . .
C007 C 0.37879(8) 0.63482(16) 0.59096(14) 0.0363(4) Uani 1 1 d . . . . .
H007 H 0.337940 0.638966 0.582913 0.044 Uiso 1 1 calc R U . . .
C008 C 0.41168(7) 0.19694(16) 0.68753(13) 0.0348(4) Uani 1 1 d . . . . .
C009 C 0.25889(7) 0.44065(16) 0.52047(13) 0.0346(4) Uani 1 1 d . . . . .
C00A C 0.30432(7) 0.39236(15) 0.50294(12) 0.0317(3) Uani 1 1 d . . . . .
C00B C 0.38322(7) 0.32009(16) 0.68052(12) 0.0326(4) Uani 1 1 d . . . . .
C00C C 0.37569(8) 0.37401(17) 0.76251(13) 0.0370(4) Uani 1 1 d . . . . .
H00C H 0.357744 0.459627 0.759188 0.044 Uiso 1 1 calc R U . . .
C00D C 0.46464(8) 0.50710(17) 0.60148(14) 0.0379(4) Uani 1 1 d . . . . .
H00D H 0.483077 0.423217 0.600550 0.046 Uiso 1 1 calc R U . . .
C00E C 0.43114(8) 0.12213(18) 0.77463(14) 0.0411(4) Uani 1 1 d . . . . .
H00E H 0.450202 0.037780 0.778413 0.049 Uiso 1 1 calc R U . . .
C00F C 0.35496(7) 0.26245(15) 0.42762(13) 0.0327(4) Uani 1 1 d . . . . .
C00G C 0.36950(7) 0.37967(15) 0.57756(12) 0.0302(3) Uani 1 1 d . . . . .
C00H C 0.41531(7) 0.16311(15) 0.59111(13) 0.0341(4) Uani 1 1 d . . . . .
C00I C 0.49768(8) 0.62417(18) 0.61606(15) 0.0424(4) Uani 1 1 d . . . . .
H00I H 0.538713 0.620183 0.625213 0.051 Uiso 1 1 calc R U . . .
C00J C 0.25705(8) 0.33217(17) 0.31269(13) 0.0390(4) Uani 1 1 d . . . . .
H00J H 0.220773 0.380503 0.297977 0.047 Uiso 1 1 calc R U . . .
C00K C 0.47139(8) 0.74690(17) 0.61741(13) 0.0382(4) Uani 1 1 d . . . . .
H00K H 0.494088 0.827174 0.626570 0.046 Uiso 1 1 calc R U . . .
C00L C 0.41201(8) 0.75214(16) 0.60539(14) 0.0385(4) Uani 1 1 d . . . . .
H00L H 0.393835 0.836145 0.606993 0.046 Uiso 1 1 calc R U . . .
C00M C 0.36466(8) 0.18814(17) 0.35520(14) 0.0392(4) Uani 1 1 d . . . . .
H00M H 0.400895 0.139732 0.369652 0.047 Uiso 1 1 calc R U . . .
C00N C 0.42203(9) 0.17380(19) 0.85583(14) 0.0455(5) Uani 1 1 d . . . . .
H00N H 0.434130 0.123642 0.915984 0.055 Uiso 1 1 calc R U . . .
C00O C 0.39521(8) 0.29897(19) 0.85006(14) 0.0429(4) Uani 1 1 d . . . . .
H00O H 0.390135 0.333842 0.907083 0.051 Uiso 1 1 calc R U . . .
C00P C 0.31934(9) 0.18676(19) 0.26012(14) 0.0445(4) Uani 1 1 d . . . . .
H00P H 0.324625 0.135991 0.208837 0.053 Uiso 1 1 calc R U . . .
C00Q C 0.26674(9) 0.25808(19) 0.23905(14) 0.0442(4) Uani 1 1 d . . . . .
H00Q H 0.236772 0.256477 0.173345 0.053 Uiso 1 1 calc R 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
F001 C009 1.321(2) . ?
F002 C009 1.327(2) . ?
O003 C00H 1.214(2) . ?
N004 C00F 1.415(2) . ?
N004 C00G 1.485(2) . ?
N004 C00H 1.395(2) . ?
C005 C00A 1.475(2) . ?
C005 C00F 1.402(2) . ?
C005 C00J 1.391(2) . ?
C006 C007 1.386(2) . ?
C006 C00D 1.387(2) . ?
C006 C00G 1.542(2) . ?
C007 H007 0.9500 . ?
C007 C00L 1.388(2) . ?
C008 C00B 1.391(2) . ?
C008 C00E 1.386(2) . ?
C008 C00H 1.478(2) . ?
C009 C00A 1.312(2) . ?
C00A C00G 1.534(2) . ?
C00B C00C 1.383(2) . ?
C00B C00G 1.523(2) . ?
C00C H00C 0.9500 . ?
C00C C00O 1.392(3) . ?
C00D H00D 0.9500 . ?
C00D C00I 1.383(2) . ?
C00E H00E 0.9500 . ?
C00E C00N 1.382(3) . ?
C00F C00M 1.380(2) . ?
C00I H00I 0.9500 . ?
C00I C00K 1.382(2) . ?
C00J H00J 0.9500 . ?
C00J C00Q 1.393(3) . ?
C00K H00K 0.9500 . ?
C00K C00L 1.379(3) . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00M C00P 1.393(3) . ?
C00N H00N 0.9500 . ?
C00N C00O 1.393(3) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00P C00Q 1.384(3) . ?
C00Q H00Q 0.9500 . ?

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
C00F N004 C00G 110.09(13) . . ?
C00H N004 C00F 122.60(13) . . ?
C00H N004 C00G 112.78(13) . . ?
C00F C005 C00A 107.98(14) . . ?
C00J C005 C00A 132.37(16) . . ?
C00J C005 C00F 119.54(16) . . ?
C007 C006 C00D 119.02(15) . . ?
C007 C006 C00G 121.30(14) . . ?
C00D C006 C00G 119.56(14) . . ?
C006 C007 H007 119.7 . . ?
C006 C007 C00L 120.55(16) . . ?
C00L C007 H007 119.7 . . ?
C00B C008 C00H 109.95(14) . . ?
C00E C008 C00B 121.66(17) . . ?
C00E C008 C00H 128.37(16) . . ?
F001 C009 F002 109.15(14) . . ?
C00A C009 F001 126.50(16) . . ?
C00A C009 F002 124.34(16) . . ?
C005 C00A C00G 106.81(13) . . ?
C009 C00A C005 126.16(16) . . ?
C009 C00A C00G 126.97(16) . . ?
C008 C00B C00G 109.22(14) . . ?
C00C C00B C008 120.41(16) . . ?
C00C C00B C00G 130.16(15) . . ?
C00B C00C H00C 121.0 . . ?
C00B C00C C00O 117.95(17) . . ?
C00O C00C H00C 121.0 . . ?
C006 C00D H00D 119.9 . . ?
C00I C00D C006 120.30(16) . . ?
C00I C00D H00D 119.9 . . ?
C008 C00E H00E 121.0 . . ?
C00N C00E C008 118.07(17) . . ?
C00N C00E H00E 121.0 . . ?
C005 C00F N004 109.78(14) . . ?
C00M C00F N004 127.90(16) . . ?
C00M C00F C005 122.23(16) . . ?
N004 C00G C006 110.81(12) . . ?
N004 C00G C00A 101.44(12) . . ?
N004 C00G C00B 101.96(12) . . ?
C00A C00G C006 112.16(13) . . ?
C00B C00G C006 109.41(13) . . ?
C00B C00G C00A 120.04(13) . . ?
O003 C00H N004 124.75(17) . . ?
O003 C00H C008 129.35(16) . . ?
N004 C00H C008 105.88(13) . . ?
C00D C00I H00I 119.8 . . ?
C00K C00I C00D 120.45(16) . . ?
C00K C00I H00I 119.8 . . ?
C005 C00J H00J 120.7 . . ?
C005 C00J C00Q 118.51(17) . . ?
C00Q C00J H00J 120.7 . . ?
C00I C00K H00K 120.2 . . ?
C00L C00K C00I 119.61(15) . . ?
C00L C00K H00K 120.2 . . ?
C007 C00L H00L 120.0 . . ?
C00K C00L C007 120.06(16) . . ?
C00K C00L H00L 120.0 . . ?
C00F C00M H00M 121.2 . . ?
C00F C00M C00P 117.51(17) . . ?
C00P C00M H00M 121.2 . . ?
C00E C00N H00N 119.8 . . ?
C00E C00N C00O 120.44(17) . . ?
C00O C00N H00N 119.8 . . ?
C00C C00O C00N 121.40(18) . . ?
C00C C00O H00O 119.3 . . ?
C00N C00O H00O 119.3 . . ?
C00M C00P H00P 119.4 . . ?
C00Q C00P C00M 121.16(17) . . ?
C00Q C00P H00P 119.4 . . ?
C00J C00Q H00Q 119.5 . . ?
C00P C00Q C00J 121.05(17) . . ?
C00P C00Q H00Q 119.5 . . ?

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
F001 C009 C00A C005 176.35(14) . . . . ?
F001 C009 C00A C00G -0.5(3) . . . . ?
F002 C009 C00A C005 -4.8(3) . . . . ?
F002 C009 C00A C00G 178.34(14) . . . . ?
N004 C00F C00M C00P 176.87(16) . . . . ?
C005 C00A C00G N004 -18.89(15) . . . . ?
C005 C00A C00G C006 99.40(14) . . . . ?
C005 C00A C00G C00B -130.06(14) . . . . ?
C005 C00F C00M C00P 0.5(2) . . . . ?
C005 C00J C00Q C00P 0.4(3) . . . . ?
C006 C007 C00L C00K -0.2(3) . . . . ?
C006 C00D C00I C00K -0.1(3) . . . . ?
C007 C006 C00D C00I -0.8(3) . . . . ?
C007 C006 C00G N004 153.16(15) . . . . ?
C007 C006 C00G C00A 40.6(2) . . . . ?
C007 C006 C00G C00B -95.19(18) . . . . ?
C008 C00B C00C C00O -2.5(2) . . . . ?
C008 C00B C00G N004 0.90(16) . . . . ?
C008 C00B C00G C006 -116.47(14) . . . . ?
C008 C00B C00G C00A 111.79(16) . . . . ?
C008 C00E C00N C00O -1.4(3) . . . . ?
C009 C00A C00G N004 158.48(16) . . . . ?
C009 C00A C00G C006 -83.2(2) . . . . ?
C009 C00A C00G C00B 47.3(2) . . . . ?
C00A C005 C00F N004 -1.37(17) . . . . ?
C00A C005 C00F C00M 175.57(15) . . . . ?
C00A C005 C00J C00Q -175.06(16) . . . . ?
C00B C008 C00E C00N -0.6(3) . . . . ?
C00B C008 C00H O003 -173.71(16) . . . . ?
C00B C008 C00H N004 4.72(17) . . . . ?
C00B C00C C00O C00N 0.5(3) . . . . ?
C00C C00B C00G N004 175.56(16) . . . . ?
C00C C00B C00G C006 58.2(2) . . . . ?
C00C C00B C00G C00A -73.5(2) . . . . ?
C00D C006 C007 C00L 0.9(3) . . . . ?
C00D C006 C00G N004 -30.9(2) . . . . ?
C00D C006 C00G C00A -143.47(16) . . . . ?
C00D C006 C00G C00B 80.76(18) . . . . ?
C00D C00I C00K C00L 0.8(3) . . . . ?
C00E C008 C00B C00C 2.6(2) . . . . ?
C00E C008 C00B C00G 177.87(15) . . . . ?
C00E C008 C00H O003 4.8(3) . . . . ?
C00E C008 C00H N004 -176.72(16) . . . . ?
C00E C00N C00O C00C 1.4(3) . . . . ?
C00F N004 C00G C006 -100.62(15) . . . . ?
C00F N004 C00G C00A 18.64(16) . . . . ?
C00F N004 C00G C00B 143.03(13) . . . . ?
C00F N004 C00H O003 39.0(2) . . . . ?
C00F N004 C00H C008 -139.49(15) . . . . ?
C00F C005 C00A C009 -164.20(16) . . . . ?
C00F C005 C00A C00G 13.19(17) . . . . ?
C00F C005 C00J C00Q 0.5(2) . . . . ?
C00F C00M C00P C00Q 0.4(3) . . . . ?
C00G N004 C00F C005 -11.63(17) . . . . ?
C00G N004 C00F C00M 171.66(16) . . . . ?
C00G N004 C00H O003 174.33(15) . . . . ?
C00G N004 C00H C008 -4.20(17) . . . . ?
C00G C006 C007 C00L 176.88(16) . . . . ?
C00G C006 C00D C00I -176.80(16) . . . . ?
C00G C00B C00C C00O -176.67(16) . . . . ?
C00H N004 C00F C005 124.69(16) . . . . ?
C00H N004 C00F C00M -52.0(2) . . . . ?
C00H N004 C00G C006 118.52(14) . . . . ?
C00H N004 C00G C00A -122.23(14) . . . . ?
C00H N004 C00G C00B 2.17(16) . . . . ?
C00H C008 C00B C00C -178.73(14) . . . . ?
C00H C008 C00B C00G -3.46(18) . . . . ?
C00H C008 C00E C00N -178.99(16) . . . . ?
C00I C00K C00L C007 -0.7(3) . . . . ?
C00J C005 C00A C009 11.8(3) . . . . ?
C00J C005 C00A C00G -170.83(17) . . . . ?
C00J C005 C00F N004 -177.95(14) . . . . ?
C00J C005 C00F C00M -1.0(2) . . . . ?
C00M C00P C00Q C00J -0.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2101086'
loop_
_audit_author_name
_audit_author_address
'gang wang'
;Xinjiang University
China
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_audit_creation_date             2021-05-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 F2 N O'
_chemical_formula_sum            'C17 H11 F2 N O'
_chemical_formula_weight         283.27
_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 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   13.160(4)
_cell_length_b                   7.282(2)
_cell_length_c                   14.200(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.631(6)
_cell_angle_gamma                90
_cell_volume                     1341.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    800
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.19
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0561 before and 0.0363 after correction.
The Ratio of minimum to maximum transmission is 0.8710.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6537
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.910
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1140
_reflns_number_total             2358
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      0.974
_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)+(0.0356P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.1102
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 0.92954(12) 0.6181(2) 0.43924(12) 0.0858(6) Uani 1 1 d . . . . .
F2 F 0.91023(12) 0.6247(2) 0.28551(12) 0.0871(6) Uani 1 1 d . . . . .
O1 O 0.49313(16) 0.2911(3) 0.39618(14) 0.0809(7) Uani 1 1 d . . . . .
N1 N 0.59894(15) 0.5434(3) 0.39120(16) 0.0530(6) Uani 1 1 d . . . . .
C1 C 0.7615(2) 0.6101(4) 0.35459(18) 0.0486(7) Uani 1 1 d . . . . .
C2 C 0.70190(19) 0.6065(4) 0.43911(19) 0.0495(7) Uani 1 1 d . . . . .
C3 C 0.6845(2) 0.6132(4) 0.26744(19) 0.0512(7) Uani 1 1 d . . . . .
C4 C 0.7279(2) 0.4665(4) 0.51823(19) 0.0528(7) Uani 1 1 d . . . . .
C5 C 0.5683(2) 0.3814(4) 0.4298(2) 0.0598(8) Uani 1 1 d . . . . .
C6 C 0.6467(2) 0.3452(4) 0.5151(2) 0.0559(8) Uani 1 1 d . . . . .
C7 C 0.5884(2) 0.5753(4) 0.2910(2) 0.0545(8) Uani 1 1 d . . . . .
C8 C 0.8602(3) 0.6184(4) 0.3598(2) 0.0607(8) Uani 1 1 d . . . . .
C9 C 0.8110(2) 0.4580(4) 0.5920(2) 0.0665(9) Uani 1 1 d . . . . .
H9 H 0.865191 0.540940 0.595390 0.080 Uiso 1 1 calc R U . . .
C10 C 0.6948(2) 0.8000(4) 0.47909(19) 0.0615(8) Uani 1 1 d . . . . .
H10A H 0.665050 0.881135 0.428662 0.092 Uiso 1 1 calc R U . . .
H10B H 0.762538 0.842351 0.505897 0.092 Uiso 1 1 calc R U . . .
H10C H 0.652296 0.797946 0.527842 0.092 Uiso 1 1 calc R U . . .
C11 C 0.4995(2) 0.5680(4) 0.2242(2) 0.0702(9) Uani 1 1 d . . . . .
H11 H 0.435781 0.543052 0.241542 0.084 Uiso 1 1 calc R U . . .
C12 C 0.6919(3) 0.6448(4) 0.1722(2) 0.0649(8) Uani 1 1 d . . . . .
H12 H 0.755328 0.669533 0.154367 0.078 Uiso 1 1 calc R U . . .
C13 C 0.6461(3) 0.2100(4) 0.5840(3) 0.0774(10) Uani 1 1 d . . . . .
H13 H 0.591137 0.128755 0.581379 0.093 Uiso 1 1 calc R U . . .
C14 C 0.8114(3) 0.3229(5) 0.6605(2) 0.0809(10) Uani 1 1 d . . . . .
H14 H 0.867316 0.314112 0.709964 0.097 Uiso 1 1 calc R U . . .
C15 C 0.7304(3) 0.2008(5) 0.6570(2) 0.0858(11) Uani 1 1 d . . . . .
H15 H 0.732533 0.111397 0.704102 0.103 Uiso 1 1 calc R U . . .
C16 C 0.5098(3) 0.6000(4) 0.1295(2) 0.0825(10) Uani 1 1 d . . . . .
H16 H 0.451626 0.594760 0.082281 0.099 Uiso 1 1 calc R U . . .
C17 C 0.6032(3) 0.6388(4) 0.1044(2) 0.0764(10) Uani 1 1 d . . . . .
H17 H 0.607277 0.661652 0.040738 0.092 Uiso 1 1 calc R 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
F1 C8 1.327(3) . ?
F2 C8 1.334(3) . ?
O1 C5 1.217(3) . ?
N1 C2 1.484(3) . ?
N1 C5 1.388(3) . ?
N1 C7 1.425(3) . ?
C1 C2 1.540(3) . ?
C1 C3 1.463(3) . ?
C1 C8 1.290(3) . ?
C2 C4 1.513(3) . ?
C2 C10 1.527(3) . ?
C3 C7 1.389(3) . ?
C3 C12 1.391(4) . ?
C4 C6 1.381(4) . ?
C4 C9 1.383(3) . ?
C5 C6 1.477(4) . ?
C6 C13 1.389(4) . ?
C7 C11 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C14 1.383(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C16 1.394(4) . ?
C12 H12 0.9300 . ?
C12 C17 1.383(4) . ?
C13 H13 0.9300 . ?
C13 C15 1.388(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.366(4) . ?
C17 H17 0.9300 . ?

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
C5 N1 C2 112.7(2) . . ?
C5 N1 C7 123.1(2) . . ?
C7 N1 C2 109.6(2) . . ?
C3 C1 C2 106.7(2) . . ?
C8 C1 C2 126.6(3) . . ?
C8 C1 C3 126.6(3) . . ?
N1 C2 C1 101.1(2) . . ?
N1 C2 C4 102.0(2) . . ?
N1 C2 C10 110.4(2) . . ?
C4 C2 C1 120.6(2) . . ?
C4 C2 C10 111.4(2) . . ?
C10 C2 C1 110.2(2) . . ?
C7 C3 C1 108.8(2) . . ?
C7 C3 C12 118.8(3) . . ?
C12 C3 C1 132.4(3) . . ?
C6 C4 C2 109.3(2) . . ?
C6 C4 C9 120.3(3) . . ?
C9 C4 C2 130.1(3) . . ?
O1 C5 N1 125.1(3) . . ?
O1 C5 C6 129.4(3) . . ?
N1 C5 C6 105.5(3) . . ?
C4 C6 C5 110.0(3) . . ?
C4 C6 C13 121.8(3) . . ?
C13 C6 C5 128.2(3) . . ?
C3 C7 N1 109.4(2) . . ?
C11 C7 N1 127.6(3) . . ?
C11 C7 C3 123.0(3) . . ?
F1 C8 F2 108.2(3) . . ?
C1 C8 F1 126.2(3) . . ?
C1 C8 F2 125.6(3) . . ?
C4 C9 H9 120.8 . . ?
C14 C9 C4 118.3(3) . . ?
C14 C9 H9 120.8 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11 121.7 . . ?
C7 C11 C16 116.7(3) . . ?
C16 C11 H11 121.7 . . ?
C3 C12 H12 120.5 . . ?
C17 C12 C3 118.9(3) . . ?
C17 C12 H12 120.5 . . ?
C6 C13 H13 121.2 . . ?
C15 C13 C6 117.5(3) . . ?
C15 C13 H13 121.2 . . ?
C9 C14 H14 119.3 . . ?
C15 C14 C9 121.3(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C15 H15 119.6 . . ?
C14 C15 C13 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C11 C16 H16 119.2 . . ?
C17 C16 C11 121.5(3) . . ?
C17 C16 H16 119.2 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.1(3) . . ?
C16 C17 H17 119.4 . . ?

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 C5 C6 C4 169.9(3) . . . . ?
O1 C5 C6 C13 -8.7(5) . . . . ?
N1 C2 C4 C6 -1.7(3) . . . . ?
N1 C2 C4 C9 -175.0(3) . . . . ?
N1 C5 C6 C4 -8.4(3) . . . . ?
N1 C5 C6 C13 172.9(2) . . . . ?
N1 C7 C11 C16 -178.3(3) . . . . ?
C1 C2 C4 C6 -112.4(3) . . . . ?
C1 C2 C4 C9 74.3(4) . . . . ?
C1 C3 C7 N1 -1.1(3) . . . . ?
C1 C3 C7 C11 -179.9(2) . . . . ?
C1 C3 C12 C17 -179.8(3) . . . . ?
C2 N1 C5 O1 -171.0(2) . . . . ?
C2 N1 C5 C6 7.4(3) . . . . ?
C2 N1 C7 C3 14.2(3) . . . . ?
C2 N1 C7 C11 -167.1(3) . . . . ?
C2 C1 C3 C7 -11.7(3) . . . . ?
C2 C1 C3 C12 168.6(3) . . . . ?
C2 C1 C8 F1 2.8(5) . . . . ?
C2 C1 C8 F2 -178.7(3) . . . . ?
C2 C4 C6 C5 6.2(3) . . . . ?
C2 C4 C6 C13 -175.1(2) . . . . ?
C2 C4 C9 C14 174.1(2) . . . . ?
C3 C1 C2 N1 18.8(3) . . . . ?
C3 C1 C2 C4 130.0(2) . . . . ?
C3 C1 C2 C10 -97.9(2) . . . . ?
C3 C1 C8 F1 179.0(2) . . . . ?
C3 C1 C8 F2 -2.6(5) . . . . ?
C3 C7 C11 C16 0.3(4) . . . . ?
C3 C12 C17 C16 -1.0(4) . . . . ?
C4 C6 C13 C15 0.1(4) . . . . ?
C4 C9 C14 C15 -1.1(4) . . . . ?
C5 N1 C2 C1 121.0(2) . . . . ?
C5 N1 C2 C4 -3.8(3) . . . . ?
C5 N1 C2 C10 -122.3(2) . . . . ?
C5 N1 C7 C3 -122.0(3) . . . . ?
C5 N1 C7 C11 56.8(4) . . . . ?
C5 C6 C13 C15 178.5(3) . . . . ?
C6 C4 C9 C14 1.5(4) . . . . ?
C6 C13 C15 C14 0.3(5) . . . . ?
C7 N1 C2 C1 -20.0(3) . . . . ?
C7 N1 C2 C4 -144.9(2) . . . . ?
C7 N1 C2 C10 96.6(2) . . . . ?
C7 N1 C5 O1 -36.0(4) . . . . ?
C7 N1 C5 C6 142.4(2) . . . . ?
C7 C3 C12 C17 0.5(4) . . . . ?
C7 C11 C16 C17 -0.8(5) . . . . ?
C8 C1 C2 N1 -164.4(3) . . . . ?
C8 C1 C2 C4 -53.2(4) . . . . ?
C8 C1 C2 C10 78.8(4) . . . . ?
C8 C1 C3 C7 171.6(3) . . . . ?
C8 C1 C3 C12 -8.1(5) . . . . ?
C9 C4 C6 C5 -179.7(2) . . . . ?
C9 C4 C6 C13 -1.0(4) . . . . ?
C9 C14 C15 C13 0.2(5) . . . . ?
C10 C2 C4 C6 116.1(2) . . . . ?
C10 C2 C4 C9 -57.2(3) . . . . ?
C11 C16 C17 C12 1.1(5) . . . . ?
C12 C3 C7 N1 178.6(2) . . . . ?
C12 C3 C7 C11 -0.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2103217'
loop_
_audit_author_name
_audit_author_address
'gang wang'
;Xinjiang University
China
;
_audit_update_record             
;
2021-08-14 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_audit_creation_date             2021-08-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H30 N2 O2'
_chemical_formula_sum            'C25 H30 N2 O2'
_chemical_formula_weight         390.51
_chemical_absolute_configuration .
_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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'y, -x, -z'
'-x, -y, z'
'-y, x, -z'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   20.1920(8)
_cell_length_b                   20.1920(8)
_cell_length_c                   11.0430(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4502.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2911
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.156
_cell_measurement_theta_min      2.253
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1144 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8023.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1637
_diffrn_reflns_av_unetI/netI     0.1123
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21458
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.734
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1958
_reflns_number_total             3966
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3966
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1518
_refine_ls_R_factor_gt           0.0709
_refine_ls_restrained_S_all      0.952
_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)+(0.0707P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1737
_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.a Ternary CH refined with riding coordinates:
 C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C11(H11A,H11B), C16(H16A,H16B), C19(H19A,H19B),
 C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C9(H9), C12(H12), C14(H14), C17(H17), C21(H21)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C), C18(H18A,H18B,H18C)
;
_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
O1 O 0.24019(19) 0.7433(2) 0.8483(4) 0.0657(11) Uani 1 1 d . . . . .
O2 O 0.0292(2) 0.7298(3) 0.9037(4) 0.0924(16) Uani 1 1 d . . . . .
N1 N 0.0924(2) 0.7725(2) 0.7491(4) 0.0558(13) Uani 1 1 d . . . . .
N2 N 0.3166(3) 0.7605(3) 0.7035(4) 0.0618(14) Uani 1 1 d . . . . .
C1 C 0.1738(4) 0.5651(4) 0.6684(8) 0.094(2) Uani 1 1 d . . . . .
H1 H 0.199010 0.531641 0.633291 0.113 Uiso 1 1 calc R U . . .
C2 C 0.1304(5) 0.5500(4) 0.7601(8) 0.103(3) Uani 1 1 d . . . . .
H2 H 0.127046 0.506337 0.786085 0.123 Uiso 1 1 calc R U . . .
C3 C 0.3681(3) 0.7341(4) 0.7825(6) 0.0725(19) Uani 1 1 d . . . . .
H3A H 0.356355 0.743433 0.865866 0.087 Uiso 1 1 calc R U . . .
H3B H 0.409331 0.756934 0.765307 0.087 Uiso 1 1 calc R U . . .
C4 C 0.4443(6) 0.5686(6) 0.8532(14) 0.178(5) Uani 1 1 d . . . . .
H4A H 0.467985 0.557919 0.780397 0.267 Uiso 1 1 calc R U . . .
H4B H 0.402567 0.545908 0.853626 0.267 Uiso 1 1 calc R U . . .
H4C H 0.469915 0.555107 0.922220 0.267 Uiso 1 1 calc R U . . .
C5 C 0.3945(4) 0.8702(4) 0.4590(6) 0.089(2) Uani 1 1 d . . . . .
H5A H 0.368275 0.855307 0.390716 0.107 Uiso 1 1 calc R U . . .
H5B H 0.436048 0.845997 0.457599 0.107 Uiso 1 1 calc R U . . .
C6 C 0.1708(3) 0.8536(3) 0.7405(6) 0.0588(17) Uani 1 1 d . . . . .
C7 C 0.1801(3) 0.6288(4) 0.6282(7) 0.078(2) Uani 1 1 d . . . . .
H7 H 0.208950 0.638836 0.565221 0.094 Uiso 1 1 calc R U . . .
C8 C 0.1073(3) 0.7613(3) 0.5295(5) 0.0708(19) Uani 1 1 d . . . . .
H8A H 0.066689 0.736790 0.524680 0.106 Uiso 1 1 calc R U . . .
H8B H 0.137080 0.746384 0.467418 0.106 Uiso 1 1 calc R U . . .
H8C H 0.098329 0.807606 0.518415 0.106 Uiso 1 1 calc R U . . .
C9 C 0.1971(4) 0.9142(4) 0.7673(7) 0.085(2) Uani 1 1 d . . . . .
H9 H 0.237175 0.927451 0.733355 0.103 Uiso 1 1 calc R U . . .
C10 C 0.2539(3) 0.7632(3) 0.7474(6) 0.0542(15) Uani 1 1 d . . . . .
C11 C 0.4333(4) 0.6382(4) 0.8583(10) 0.116(3) Uani 1 1 d . . . . .
H11A H 0.474365 0.660981 0.839959 0.140 Uiso 1 1 calc R U . . .
H11B H 0.420450 0.650207 0.940120 0.140 Uiso 1 1 calc R U . . .
C12 C 0.1040(5) 0.9373(5) 0.8921(9) 0.106(3) Uani 1 1 d . . . . .
H12 H 0.081575 0.965801 0.943841 0.127 Uiso 1 1 calc R U . . .
C13 C 0.1436(3) 0.6773(3) 0.6817(6) 0.0573(17) Uani 1 1 d . . . . .
C14 C 0.0761(4) 0.8770(4) 0.8644(7) 0.083(2) Uani 1 1 d . . . . .
H14 H 0.035530 0.864483 0.896921 0.099 Uiso 1 1 calc R U . . .
C15 C 0.0992(3) 0.6620(3) 0.7748(6) 0.0620(18) Uani 1 1 d . . . . .
C16 C 0.3395(3) 0.7808(3) 0.5823(6) 0.0694(19) Uani 1 1 d . . . . .
H16A H 0.304645 0.771724 0.524111 0.083 Uiso 1 1 calc R U . . .
H16B H 0.377525 0.754016 0.560241 0.083 Uiso 1 1 calc R U . . .
C17 C 0.0916(4) 0.5978(4) 0.8153(7) 0.087(2) Uani 1 1 d . . . . .
H17 H 0.061867 0.587154 0.876526 0.104 Uiso 1 1 calc R U . . .
C18 C 0.4090(4) 0.9431(4) 0.4442(8) 0.125(3) Uani 1 1 d . . . . .
H18A H 0.431488 0.950288 0.368738 0.188 Uiso 1 1 calc R U . . .
H18B H 0.436432 0.957920 0.509722 0.188 Uiso 1 1 calc R U . . .
H18C H 0.368123 0.967440 0.444536 0.188 Uiso 1 1 calc R U . . .
C19 C 0.3586(3) 0.8538(3) 0.5734(6) 0.0741(19) Uani 1 1 d . . . . .
H19A H 0.318735 0.880550 0.578059 0.089 Uiso 1 1 calc R U . . .
H19B H 0.386345 0.865231 0.641891 0.089 Uiso 1 1 calc R U . . .
C20 C 0.2005(3) 0.7956(3) 0.6702(5) 0.0561(16) Uani 1 1 d . . . . .
H20 H 0.218100 0.810011 0.591754 0.067 Uiso 1 1 calc R U . . .
C21 C 0.1629(5) 0.9561(4) 0.8465(9) 0.100(3) Uani 1 1 d . . . . .
H21 H 0.180742 0.996984 0.867587 0.120 Uiso 1 1 calc R U . . .
C22 C 0.1392(3) 0.7504(3) 0.6544(5) 0.0527(15) Uani 1 1 d . . . . .
C23 C 0.0678(3) 0.7228(4) 0.8206(6) 0.0669(18) Uani 1 1 d . . . . .
C24 C 0.3791(4) 0.6620(4) 0.7695(7) 0.086(2) Uani 1 1 d . . . . .
H24A H 0.392534 0.652165 0.687062 0.103 Uiso 1 1 calc R U . . .
H24B H 0.338150 0.638556 0.785641 0.103 Uiso 1 1 calc R U . . .
C25 C 0.1098(3) 0.8362(3) 0.7881(6) 0.0604(17) 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
O1 C10 1.216(7) . ?
O2 C23 1.212(7) . ?
N1 C22 1.480(7) . ?
N1 C23 1.371(8) . ?
N1 C25 1.401(8) . ?
N2 C3 1.459(7) . ?
N2 C10 1.356(7) . ?
N2 C16 1.474(8) . ?
C1 H1 0.9300 . ?
C1 C2 1.373(10) . ?
C1 C7 1.367(9) . ?
C2 H2 0.9300 . ?
C2 C17 1.384(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C24 1.479(9) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 C11 1.424(12) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C18 1.510(10) . ?
C5 C19 1.494(9) . ?
C6 C9 1.368(8) . ?
C6 C20 1.526(8) . ?
C6 C25 1.385(9) . ?
C7 H7 0.9300 . ?
C7 C13 1.361(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C22 1.538(7) . ?
C9 H9 0.9300 . ?
C9 C21 1.400(10) . ?
C10 C20 1.523(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C24 1.546(11) . ?
C12 H12 0.9300 . ?
C12 C14 1.375(10) . ?
C12 C21 1.345(11) . ?
C13 C15 1.397(8) . ?
C13 C22 1.509(9) . ?
C14 H14 0.9300 . ?
C14 C25 1.360(9) . ?
C15 C17 1.380(9) . ?
C15 C23 1.471(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C19 1.527(8) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20 0.9800 . ?
C20 C22 1.548(7) . ?
C21 H21 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?

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
C23 N1 C22 114.6(5) . . ?
C23 N1 C25 125.9(5) . . ?
C25 N1 C22 109.5(5) . . ?
C3 N2 C16 114.9(5) . . ?
C10 N2 C3 117.8(5) . . ?
C10 N2 C16 127.3(5) . . ?
C2 C1 H1 119.8 . . ?
C7 C1 H1 119.8 . . ?
C7 C1 C2 120.5(8) . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C17 122.1(8) . . ?
C17 C2 H2 118.9 . . ?
N2 C3 H3A 108.7 . . ?
N2 C3 H3B 108.7 . . ?
N2 C3 C24 114.2(6) . . ?
H3A C3 H3B 107.6 . . ?
C24 C3 H3A 108.7 . . ?
C24 C3 H3B 108.7 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C11 C4 H4A 109.5 . . ?
C11 C4 H4B 109.5 . . ?
C11 C4 H4C 109.5 . . ?
H5A C5 H5B 107.7 . . ?
C18 C5 H5A 108.8 . . ?
C18 C5 H5B 108.8 . . ?
C19 C5 H5A 108.8 . . ?
C19 C5 H5B 108.8 . . ?
C19 C5 C18 113.7(7) . . ?
C9 C6 C20 130.1(6) . . ?
C9 C6 C25 119.3(6) . . ?
C25 C6 C20 110.4(5) . . ?
C1 C7 H7 120.5 . . ?
C13 C7 C1 119.1(7) . . ?
C13 C7 H7 120.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C22 C8 H8A 109.5 . . ?
C22 C8 H8B 109.5 . . ?
C22 C8 H8C 109.5 . . ?
C6 C9 H9 120.5 . . ?
C6 C9 C21 119.0(7) . . ?
C21 C9 H9 120.5 . . ?
O1 C10 N2 121.8(6) . . ?
O1 C10 C20 119.6(6) . . ?
N2 C10 C20 118.5(6) . . ?
C4 C11 H11A 109.0 . . ?
C4 C11 H11B 109.0 . . ?
C4 C11 C24 113.1(9) . . ?
H11A C11 H11B 107.8 . . ?
C24 C11 H11A 109.0 . . ?
C24 C11 H11B 109.0 . . ?
C14 C12 H12 119.0 . . ?
C21 C12 H12 119.0 . . ?
C21 C12 C14 122.0(8) . . ?
C7 C13 C15 120.5(6) . . ?
C7 C13 C22 130.4(6) . . ?
C15 C13 C22 109.0(5) . . ?
C12 C14 H14 121.0 . . ?
C25 C14 C12 117.9(7) . . ?
C25 C14 H14 121.0 . . ?
C13 C15 C23 110.2(6) . . ?
C17 C15 C13 121.1(7) . . ?
C17 C15 C23 128.6(7) . . ?
N2 C16 H16A 108.8 . . ?
N2 C16 H16B 108.8 . . ?
N2 C16 C19 113.9(5) . . ?
H16A C16 H16B 107.7 . . ?
C19 C16 H16A 108.8 . . ?
C19 C16 H16B 108.8 . . ?
C2 C17 H17 121.6 . . ?
C15 C17 C2 116.7(7) . . ?
C15 C17 H17 121.6 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C5 C19 C16 113.0(6) . . ?
C5 C19 H19A 109.0 . . ?
C5 C19 H19B 109.0 . . ?
C16 C19 H19A 109.0 . . ?
C16 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C6 C20 H20 111.4 . . ?
C6 C20 C22 101.3(4) . . ?
C10 C20 C6 108.8(5) . . ?
C10 C20 H20 111.4 . . ?
C10 C20 C22 112.0(5) . . ?
C22 C20 H20 111.4 . . ?
C9 C21 H21 120.0 . . ?
C12 C21 C9 119.9(7) . . ?
C12 C21 H21 120.0 . . ?
N1 C22 C8 108.8(4) . . ?
N1 C22 C13 101.0(5) . . ?
N1 C22 C20 104.6(4) . . ?
C8 C22 C20 110.5(5) . . ?
C13 C22 C8 110.1(5) . . ?
C13 C22 C20 120.6(5) . . ?
O2 C23 N1 125.6(7) . . ?
O2 C23 C15 129.5(7) . . ?
N1 C23 C15 104.9(6) . . ?
C3 C24 C11 110.5(7) . . ?
C3 C24 H24A 109.5 . . ?
C3 C24 H24B 109.5 . . ?
C11 C24 H24A 109.5 . . ?
C11 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
C6 C25 N1 109.8(5) . . ?
C14 C25 N1 128.4(6) . . ?
C14 C25 C6 121.8(7) . . ?

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 C10 C20 C6 55.8(7) . . . . ?
O1 C10 C20 C22 -55.4(7) . . . . ?
N2 C3 C24 C11 -178.7(6) . . . . ?
N2 C10 C20 C6 -120.7(6) . . . . ?
N2 C10 C20 C22 128.2(5) . . . . ?
N2 C16 C19 C5 168.0(5) . . . . ?
C1 C2 C17 C15 -1.0(12) . . . . ?
C1 C7 C13 C15 -1.2(10) . . . . ?
C1 C7 C13 C22 -178.2(7) . . . . ?
C2 C1 C7 C13 1.0(11) . . . . ?
C3 N2 C10 O1 -1.2(9) . . . . ?
C3 N2 C10 C20 175.2(5) . . . . ?
C3 N2 C16 C19 -92.9(7) . . . . ?
C4 C11 C24 C3 177.8(9) . . . . ?
C6 C9 C21 C12 -2.0(12) . . . . ?
C6 C20 C22 N1 -19.9(5) . . . . ?
C6 C20 C22 C8 97.1(5) . . . . ?
C6 C20 C22 C13 -132.5(5) . . . . ?
C7 C1 C2 C17 0.1(13) . . . . ?
C7 C13 C15 C17 0.3(9) . . . . ?
C7 C13 C15 C23 177.9(6) . . . . ?
C7 C13 C22 N1 -178.3(6) . . . . ?
C7 C13 C22 C8 66.7(8) . . . . ?
C7 C13 C22 C20 -63.8(9) . . . . ?
C9 C6 C20 C10 72.5(8) . . . . ?
C9 C6 C20 C22 -169.4(7) . . . . ?
C9 C6 C25 N1 179.8(6) . . . . ?
C9 C6 C25 C14 -2.4(10) . . . . ?
C10 N2 C3 C24 91.6(7) . . . . ?
C10 N2 C16 C19 88.0(7) . . . . ?
C10 C20 C22 N1 95.9(5) . . . . ?
C10 C20 C22 C8 -147.1(5) . . . . ?
C10 C20 C22 C13 -16.7(7) . . . . ?
C12 C14 C25 N1 178.5(7) . . . . ?
C12 C14 C25 C6 1.1(10) . . . . ?
C13 C15 C17 C2 0.8(10) . . . . ?
C13 C15 C23 O2 -176.4(6) . . . . ?
C13 C15 C23 N1 2.6(7) . . . . ?
C14 C12 C21 C9 0.8(14) . . . . ?
C15 C13 C22 N1 4.4(6) . . . . ?
C15 C13 C22 C8 -110.5(5) . . . . ?
C15 C13 C22 C20 118.9(5) . . . . ?
C16 N2 C3 C24 -87.6(7) . . . . ?
C16 N2 C10 O1 177.9(6) . . . . ?
C16 N2 C10 C20 -5.7(9) . . . . ?
C17 C15 C23 O2 0.9(12) . . . . ?
C17 C15 C23 N1 179.9(6) . . . . ?
C18 C5 C19 C16 175.4(6) . . . . ?
C20 C6 C9 C21 -172.2(7) . . . . ?
C20 C6 C25 N1 -4.3(7) . . . . ?
C20 C6 C25 C14 173.5(6) . . . . ?
C21 C12 C14 C25 -0.3(13) . . . . ?
C22 N1 C23 O2 179.5(6) . . . . ?
C22 N1 C23 C15 0.4(7) . . . . ?
C22 N1 C25 C6 -9.7(7) . . . . ?
C22 N1 C25 C14 172.7(6) . . . . ?
C22 C13 C15 C17 177.9(6) . . . . ?
C22 C13 C15 C23 -4.6(7) . . . . ?
C23 N1 C22 C8 113.0(6) . . . . ?
C23 N1 C22 C13 -3.0(6) . . . . ?
C23 N1 C22 C20 -128.9(5) . . . . ?
C23 N1 C25 C6 133.8(6) . . . . ?
C23 N1 C25 C14 -43.8(10) . . . . ?
C23 C15 C17 C2 -176.2(7) . . . . ?
C25 N1 C22 C8 -99.1(6) . . . . ?
C25 N1 C22 C13 145.0(5) . . . . ?
C25 N1 C22 C20 19.1(6) . . . . ?
C25 N1 C23 O2 37.6(10) . . . . ?
C25 N1 C23 C15 -141.4(6) . . . . ?
C25 C6 C9 C21 2.8(10) . . . . ?
C25 C6 C20 C10 -102.8(6) . . . . ?
C25 C6 C20 C22 15.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
