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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2373953'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Yunnan University
China
;
_audit_update_record             
;
2024-07-27 deposited with the CCDC.	2024-09-10 downloaded from the CCDC.
;
_audit_creation_date             2024-02-27
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2024,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_diffrn_source_power             0.07
_chemical_name_common            ?
_chemical_formula_sum            'C18 H17 F N2 O2'
_chemical_formula_moiety         'C18 H17 F N2 O2'
_chemical_formula_weight         312.33
_exptl_crystal_colour_primary    yellow
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C30(H30A,H30B), C29(H29A,H29B), C18(H18A,H18B), C28(H28A,
 H28B), C16(H16A,H16B), C36(H36A,H36B), C17(H17A,H17B), C12(H12A,H12B),
 C34(H34A,H34B), C11(H11A,H11B), C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), C5(H5), C21(H21), C3(H3A), C23(H23), C20(H20), C2(H2), C6(H6),
  C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5103(2)
_cell_length_b                   10.3560(3)
_cell_length_c                   17.9206(4)
_cell_angle_alpha                86.6800(10)
_cell_angle_beta                 88.9640(10)
_cell_angle_gamma                75.0740(10)
_cell_volume                     1523.53(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298.15
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.71
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7263
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0857 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.9740.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.979
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      298.15
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            55404
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_theta_min         2.038
_diffrn_reflns_theta_max         28.383
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7604
_reflns_number_gt                5335
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+0.8106P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         7604
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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
O4 O 0.85425(17) 0.60615(15) 0.55529(8) 0.0514(4) Uani 1 1 d . . . . .
O1 O 0.07501(17) 0.62268(15) 0.96055(8) 0.0521(4) Uani 1 1 d . . . . .
O2 O 0.5097(2) 0.77333(16) 0.89846(10) 0.0621(4) Uani 1 1 d . . . . .
N2 N 0.49817(19) 0.33549(16) 0.90672(9) 0.0399(4) Uani 1 1 d . . . . .
F2 F 0.6053(2) 1.11355(15) 0.73896(9) 0.0882(5) Uani 1 1 d . . . . .
O3 O 0.3214(2) 0.74660(17) 0.61693(9) 0.0623(4) Uani 1 1 d . . . . .
F1 F 0.0538(2) 1.14029(15) 0.75815(10) 0.0940(5) Uani 1 1 d . . . . .
N4 N 0.51866(19) 0.61833(16) 0.38756(9) 0.0410(4) Uani 1 1 d . . . . .
N3 N 0.8013(2) 0.55259(18) 0.40796(9) 0.0496(4) Uani 1 1 d . . . . .
H3 H 0.881574 0.542553 0.438086 0.060 Uiso 1 1 calc R U . . .
N1 N 0.2310(2) 0.34661(17) 0.94776(10) 0.0489(4) Uani 1 1 d . . . . .
H1 H 0.134416 0.394164 0.956702 0.059 Uiso 1 1 calc R U . . .
C26 C 0.5972(2) 0.66336(18) 0.50096(10) 0.0377(4) Uani 1 1 d . . . . .
C27 C 0.6506(2) 0.60557(18) 0.43322(10) 0.0383(4) Uani 1 1 d . . . . .
C9 C 0.4970(2) 0.55071(19) 0.88543(10) 0.0382(4) Uani 1 1 d . . . . .
C14 C 0.5900(2) 0.4217(2) 0.88272(10) 0.0390(4) Uani 1 1 d . . . . .
C4 C 0.1554(2) 0.77614(19) 0.87580(11) 0.0400(4) Uani 1 1 d . . . . .
C22 C 0.6753(2) 0.79491(19) 0.60471(10) 0.0396(4) Uani 1 1 d . . . . .
C8 C 0.3363(2) 0.54514(19) 0.91237(10) 0.0370(4) Uani 1 1 d . . . . .
C15 C 0.3456(2) 0.40858(19) 0.92581(10) 0.0383(4) Uani 1 1 d . . . . .
C25 C 0.7129(2) 0.68061(19) 0.55419(10) 0.0385(4) Uani 1 1 d . . . . .
C10 C 0.5754(2) 0.6599(2) 0.88014(11) 0.0455(5) Uani 1 1 d . . . . .
C32 C 0.4211(2) 0.70913(19) 0.49424(11) 0.0400(4) Uani 1 1 d . . . . .
C7 C 0.1865(2) 0.64505(19) 0.91982(11) 0.0395(4) Uani 1 1 d . . . . .
C5 C 0.0542(2) 0.8887(2) 0.90553(12) 0.0485(5) Uani 1 1 d . . . . .
H5 H 0.008673 0.881433 0.952668 0.058 Uiso 1 1 calc R U . . .
C21 C 0.5537(3) 0.9110(2) 0.58917(12) 0.0463(5) Uani 1 1 d . . . . .
H21 H 0.487384 0.916419 0.547802 0.056 Uiso 1 1 calc R U . . .
C33 C 0.2946(3) 0.7504(2) 0.54974(13) 0.0483(5) Uani 1 1 d . . . . .
C31 C 0.3797(2) 0.68033(19) 0.42477(11) 0.0412(4) Uani 1 1 d . . . . .
C3 C 0.2182(3) 0.7884(2) 0.80448(11) 0.0487(5) Uani 1 1 d . . . . .
H3A H 0.284754 0.713318 0.783526 0.058 Uiso 1 1 calc R U . . .
C23 C 0.7747(3) 0.7900(2) 0.66597(12) 0.0542(6) Uani 1 1 d . . . . .
H23 H 0.858418 0.713748 0.676545 0.065 Uiso 1 1 calc R U . . .
C13 C 0.7642(2) 0.3782(2) 0.86042(12) 0.0518(5) Uani 1 1 d . . . . .
H13A H 0.781279 0.302042 0.829387 0.062 Uiso 1 1 calc R U . . .
H13B H 0.831784 0.351521 0.904507 0.062 Uiso 1 1 calc R U . . .
C30 C 0.5362(3) 0.5710(2) 0.31168(11) 0.0513(5) Uani 1 1 d . . . . .
H30A H 0.448338 0.623853 0.280409 0.062 Uiso 1 1 calc R U . . .
H30B H 0.532069 0.478185 0.312580 0.062 Uiso 1 1 calc R U . . .
C29 C 0.6977(3) 0.5847(2) 0.28085(12) 0.0560(6) Uani 1 1 d . . . . .
H29A H 0.696655 0.678617 0.275471 0.067 Uiso 1 1 calc R U . . .
H29B H 0.714970 0.548403 0.231784 0.067 Uiso 1 1 calc R U . . .
C18 C 0.5476(3) 0.1890(2) 0.91503(13) 0.0507(5) Uani 1 1 d . . . . .
H18A H 0.593668 0.160535 0.964238 0.061 Uiso 1 1 calc R U . . .
H18B H 0.629614 0.153907 0.877944 0.061 Uiso 1 1 calc R U . . .
C20 C 0.5291(3) 1.0188(2) 0.63409(13) 0.0558(6) Uani 1 1 d . . . . .
H20 H 0.447694 1.096627 0.623411 0.067 Uiso 1 1 calc R U . . .
C28 C 0.8350(3) 0.5114(2) 0.33200(11) 0.0520(5) Uani 1 1 d . . . . .
H28A H 0.847916 0.415708 0.330865 0.062 Uiso 1 1 calc R U . . .
H28B H 0.935732 0.530571 0.314734 0.062 Uiso 1 1 calc R U . . .
C2 C 0.1837(3) 0.9102(2) 0.76396(13) 0.0581(6) Uani 1 1 d . . . . .
H2 H 0.225051 0.917912 0.715997 0.070 Uiso 1 1 calc R U . . .
C6 C 0.0199(3) 1.0110(2) 0.86638(14) 0.0571(6) Uani 1 1 d . . . . .
H6 H -0.047107 1.086466 0.886771 0.069 Uiso 1 1 calc R U . . .
C16 C 0.2645(3) 0.2017(2) 0.95696(13) 0.0547(5) Uani 1 1 d . . . . .
H16A H 0.167091 0.174024 0.946330 0.066 Uiso 1 1 calc R U . . .
H16B H 0.295728 0.172992 1.008264 0.066 Uiso 1 1 calc R U . . .
C36 C 0.2119(3) 0.7071(2) 0.39444(14) 0.0571(6) Uani 1 1 d . . . . .
H36A H 0.172627 0.627079 0.400599 0.069 Uiso 1 1 calc R U . . .
H36B H 0.211386 0.733278 0.341578 0.069 Uiso 1 1 calc R U . . .
C17 C 0.4000(3) 0.1365(2) 0.90478(14) 0.0578(6) Uani 1 1 d . . . . .
H17A H 0.428643 0.040314 0.914925 0.069 Uiso 1 1 calc R U . . .
H17B H 0.363121 0.155070 0.853437 0.069 Uiso 1 1 calc R U . . .
C19 C 0.6279(3) 1.0075(2) 0.69442(12) 0.0580(6) Uani 1 1 d . . . . .
C1 C 0.0867(3) 1.0189(2) 0.79666(14) 0.0583(6) Uani 1 1 d . . . . .
C12 C 0.8098(3) 0.4940(3) 0.81733(14) 0.0620(6) Uani 1 1 d . . . . .
H12A H 0.927016 0.473333 0.811556 0.074 Uiso 1 1 calc R U . . .
H12B H 0.762248 0.505109 0.767833 0.074 Uiso 1 1 calc R U . . .
C24 C 0.7510(3) 0.8968(2) 0.71153(13) 0.0630(6) Uani 1 1 d . . . . .
H24 H 0.817237 0.893202 0.752705 0.076 Uiso 1 1 calc R U . . .
C34 C 0.1216(3) 0.7936(3) 0.52085(15) 0.0665(7) Uani 1 1 d . . . . .
H34A H 0.067237 0.724822 0.536418 0.080 Uiso 1 1 calc R U . . .
H34B H 0.065675 0.874624 0.544626 0.080 Uiso 1 1 calc R U . . .
C11 C 0.7518(3) 0.6234(3) 0.85639(14) 0.0610(6) Uani 1 1 d . . . . .
H11A H 0.818321 0.617906 0.900432 0.073 Uiso 1 1 calc R U . . .
H11B H 0.770541 0.695490 0.823321 0.073 Uiso 1 1 calc R U . . .
C35 C 0.1028(3) 0.8195(3) 0.43715(16) 0.0714(7) Uani 1 1 d . . . . .
H35A H 0.129493 0.902997 0.422591 0.086 Uiso 1 1 calc R U . . .
H35B H -0.009649 0.828749 0.423791 0.086 Uiso 1 1 calc R U . . .


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
O4 C25 1.250(2) . ?
O1 C7 1.247(2) . ?
O2 C10 1.224(2) . ?
N2 C14 1.377(3) . ?
N2 C15 1.373(2) . ?
N2 C18 1.466(2) . ?
F2 C19 1.367(2) . ?
O3 C33 1.226(3) . ?
F1 C1 1.363(3) . ?
N4 C27 1.375(2) . ?
N4 C31 1.373(2) . ?
N4 C30 1.464(2) . ?
N3 H3 0.8600 . ?
N3 C27 1.340(2) . ?
N3 C28 1.452(2) . ?
N1 H1 0.8600 . ?
N1 C15 1.340(2) . ?
N1 C16 1.453(3) . ?
C26 C27 1.401(3) . ?
C26 C25 1.434(3) . ?
C26 C32 1.455(3) . ?
C9 C14 1.369(3) . ?
C9 C8 1.456(3) . ?
C9 C10 1.452(3) . ?
C14 C13 1.488(3) . ?
C4 C7 1.495(3) . ?
C4 C5 1.387(3) . ?
C4 C3 1.388(3) . ?
C22 C25 1.497(3) . ?
C22 C21 1.387(3) . ?
C22 C23 1.388(3) . ?
C8 C15 1.403(3) . ?
C8 C7 1.430(3) . ?
C10 C11 1.511(3) . ?
C32 C33 1.451(3) . ?
C32 C31 1.370(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.385(3) . ?
C33 C34 1.516(3) . ?
C31 C36 1.489(3) . ?
C3 H3A 0.9300 . ?
C3 C2 1.384(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.519(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C29 1.510(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C28 1.511(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.509(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.363(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C2 H2 0.9300 . ?
C2 C1 1.368(3) . ?
C6 H6 0.9300 . ?
C6 C1 1.371(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.514(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C35 1.524(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 C24 1.363(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.511(3) . ?
C24 H24 0.9300 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C35 1.512(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 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
C14 N2 C18 128.42(16) . . ?
C15 N2 C14 109.11(16) . . ?
C15 N2 C18 122.43(17) . . ?
C27 N4 C30 121.96(16) . . ?
C31 N4 C27 109.15(15) . . ?
C31 N4 C30 128.88(16) . . ?
C27 N3 H3 118.5 . . ?
C27 N3 C28 122.93(17) . . ?
C28 N3 H3 118.5 . . ?
C15 N1 H1 118.9 . . ?
C15 N1 C16 122.20(17) . . ?
C16 N1 H1 118.9 . . ?
C27 C26 C25 120.12(17) . . ?
C27 C26 C32 105.03(16) . . ?
C25 C26 C32 134.30(17) . . ?
N4 C27 C26 109.09(16) . . ?
N3 C27 N4 120.18(16) . . ?
N3 C27 C26 130.57(17) . . ?
C14 C9 C8 107.49(17) . . ?
C14 C9 C10 119.37(18) . . ?
C10 C9 C8 131.18(18) . . ?
N2 C14 C13 124.18(18) . . ?
C9 C14 N2 109.08(16) . . ?
C9 C14 C13 126.70(19) . . ?
C5 C4 C7 119.08(18) . . ?
C5 C4 C3 118.52(19) . . ?
C3 C4 C7 122.33(17) . . ?
C21 C22 C25 122.48(17) . . ?
C21 C22 C23 118.35(18) . . ?
C23 C22 C25 118.92(18) . . ?
C15 C8 C9 105.36(16) . . ?
C15 C8 C7 121.51(17) . . ?
C7 C8 C9 132.89(18) . . ?
N2 C15 C8 108.94(16) . . ?
N1 C15 N2 120.32(17) . . ?
N1 C15 C8 130.56(17) . . ?
O4 C25 C26 120.28(17) . . ?
O4 C25 C22 117.66(17) . . ?
C26 C25 C22 121.79(17) . . ?
O2 C10 C9 123.56(19) . . ?
O2 C10 C11 120.5(2) . . ?
C9 C10 C11 115.75(19) . . ?
C33 C32 C26 131.51(18) . . ?
C31 C32 C26 107.87(16) . . ?
C31 C32 C33 119.29(18) . . ?
O1 C7 C4 118.09(17) . . ?
O1 C7 C8 120.82(18) . . ?
C8 C7 C4 121.01(17) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.5 . . ?
C22 C21 H21 119.4 . . ?
C20 C21 C22 121.2(2) . . ?
C20 C21 H21 119.4 . . ?
O3 C33 C32 123.4(2) . . ?
O3 C33 C34 120.3(2) . . ?
C32 C33 C34 116.2(2) . . ?
N4 C31 C36 124.86(18) . . ?
C32 C31 N4 108.83(16) . . ?
C32 C31 C36 126.28(19) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 C4 121.21(19) . . ?
C2 C3 H3A 119.4 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.0(2) . . ?
C24 C23 H23 119.5 . . ?
C14 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
C14 C13 C12 108.71(18) . . ?
H13A C13 H13B 108.3 . . ?
C12 C13 H13A 109.9 . . ?
C12 C13 H13B 109.9 . . ?
N4 C30 H30A 110.1 . . ?
N4 C30 H30B 110.1 . . ?
N4 C30 C29 108.13(17) . . ?
H30A C30 H30B 108.4 . . ?
C29 C30 H30A 110.1 . . ?
C29 C30 H30B 110.1 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
C30 C29 C28 110.80(19) . . ?
H29A C29 H29B 108.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
N2 C18 H18A 110.0 . . ?
N2 C18 H18B 110.0 . . ?
N2 C18 C17 108.63(17) . . ?
H18A C18 H18B 108.3 . . ?
C17 C18 H18A 110.0 . . ?
C17 C18 H18B 110.0 . . ?
C21 C20 H20 121.0 . . ?
C19 C20 C21 117.9(2) . . ?
C19 C20 H20 121.0 . . ?
N3 C28 C29 110.28(17) . . ?
N3 C28 H28A 109.6 . . ?
N3 C28 H28B 109.6 . . ?
C29 C28 H28A 109.6 . . ?
C29 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C3 C2 H2 121.0 . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 H2 121.0 . . ?
C5 C6 H6 120.8 . . ?
C1 C6 C5 118.4(2) . . ?
C1 C6 H6 120.8 . . ?
N1 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
N1 C16 C17 110.37(18) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C31 C36 H36A 110.1 . . ?
C31 C36 H36B 110.1 . . ?
C31 C36 C35 108.03(19) . . ?
H36A C36 H36B 108.4 . . ?
C35 C36 H36A 110.1 . . ?
C35 C36 H36B 110.1 . . ?
C18 C17 C16 110.46(18) . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C20 C19 F2 118.5(2) . . ?
C20 C19 C24 123.3(2) . . ?
C24 C19 F2 118.3(2) . . ?
F1 C1 C2 118.8(2) . . ?
F1 C1 C6 118.4(2) . . ?
C2 C1 C6 122.8(2) . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C11 C12 C13 111.93(19) . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C23 C24 H24 120.9 . . ?
C19 C24 C23 118.2(2) . . ?
C19 C24 H24 120.9 . . ?
C33 C34 H34A 108.3 . . ?
C33 C34 H34B 108.3 . . ?
H34A C34 H34B 107.4 . . ?
C35 C34 C33 116.0(2) . . ?
C35 C34 H34A 108.3 . . ?
C35 C34 H34B 108.3 . . ?
C10 C11 C12 116.12(19) . . ?
C10 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C36 C35 H35A 109.2 . . ?
C36 C35 H35B 109.2 . . ?
C34 C35 C36 112.1(2) . . ?
C34 C35 H35A 109.2 . . ?
C34 C35 H35B 109.2 . . ?
H35A C35 H35B 107.9 . . ?

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
O2 C10 C11 C12 -165.6(2) . . . . ?
N2 C14 C13 C12 164.16(18) . . . . ?
N2 C18 C17 C16 -53.7(2) . . . . ?
F2 C19 C24 C23 -179.4(2) . . . . ?
O3 C33 C34 C35 169.1(2) . . . . ?
N4 C31 C36 C35 -158.8(2) . . . . ?
N4 C30 C29 C28 55.5(2) . . . . ?
N1 C16 C17 C18 53.6(3) . . . . ?
C26 C32 C33 O3 -3.5(4) . . . . ?
C26 C32 C33 C34 179.5(2) . . . . ?
C26 C32 C31 N4 0.5(2) . . . . ?
C26 C32 C31 C36 178.66(19) . . . . ?
C27 N4 C31 C32 0.6(2) . . . . ?
C27 N4 C31 C36 -177.62(19) . . . . ?
C27 N4 C30 C29 -31.4(3) . . . . ?
C27 N3 C28 C29 23.0(3) . . . . ?
C27 C26 C25 O4 -25.7(3) . . . . ?
C27 C26 C25 C22 148.21(18) . . . . ?
C27 C26 C32 C33 165.0(2) . . . . ?
C27 C26 C32 C31 -1.3(2) . . . . ?
C9 C14 C13 C12 -18.2(3) . . . . ?
C9 C8 C15 N2 -1.6(2) . . . . ?
C9 C8 C15 N1 -176.5(2) . . . . ?
C9 C8 C7 O1 -162.65(19) . . . . ?
C9 C8 C7 C4 20.8(3) . . . . ?
C9 C10 C11 C12 19.3(3) . . . . ?
C14 N2 C15 N1 176.96(17) . . . . ?
C14 N2 C15 C8 1.4(2) . . . . ?
C14 N2 C18 C17 -151.98(19) . . . . ?
C14 C9 C8 C15 1.2(2) . . . . ?
C14 C9 C8 C7 -173.1(2) . . . . ?
C14 C9 C10 O2 -163.02(19) . . . . ?
C14 C9 C10 C11 11.9(3) . . . . ?
C14 C13 C12 C11 47.2(3) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C3 C2 C1 0.6(4) . . . . ?
C22 C21 C20 C19 -0.2(3) . . . . ?
C22 C23 C24 C19 -0.4(4) . . . . ?
C8 C9 C14 N2 -0.4(2) . . . . ?
C8 C9 C14 C13 -178.30(18) . . . . ?
C8 C9 C10 O2 -1.1(3) . . . . ?
C8 C9 C10 C11 173.8(2) . . . . ?
C15 N2 C14 C9 -0.6(2) . . . . ?
C15 N2 C14 C13 177.37(18) . . . . ?
C15 N2 C18 C17 30.6(3) . . . . ?
C15 N1 C16 C17 -28.7(3) . . . . ?
C15 C8 C7 O1 23.8(3) . . . . ?
C15 C8 C7 C4 -152.67(18) . . . . ?
C25 C26 C27 N4 -170.99(17) . . . . ?
C25 C26 C27 N3 4.3(3) . . . . ?
C25 C26 C32 C33 -23.8(4) . . . . ?
C25 C26 C32 C31 169.8(2) . . . . ?
C25 C22 C21 C20 -175.38(19) . . . . ?
C25 C22 C23 C24 175.9(2) . . . . ?
C10 C9 C14 N2 165.40(16) . . . . ?
C10 C9 C14 C13 -12.5(3) . . . . ?
C10 C9 C8 C15 -162.29(19) . . . . ?
C10 C9 C8 C7 23.4(3) . . . . ?
C32 C26 C27 N4 1.7(2) . . . . ?
C32 C26 C27 N3 176.9(2) . . . . ?
C32 C26 C25 O4 164.2(2) . . . . ?
C32 C26 C25 C22 -21.9(3) . . . . ?
C32 C33 C34 C35 -13.7(3) . . . . ?
C32 C31 C36 C35 23.2(3) . . . . ?
C7 C4 C5 C6 -178.85(19) . . . . ?
C7 C4 C3 C2 178.0(2) . . . . ?
C7 C8 C15 N2 173.51(16) . . . . ?
C7 C8 C15 N1 -1.5(3) . . . . ?
C5 C4 C7 O1 32.8(3) . . . . ?
C5 C4 C7 C8 -150.59(19) . . . . ?
C5 C4 C3 C2 1.1(3) . . . . ?
C5 C6 C1 F1 -179.5(2) . . . . ?
C5 C6 C1 C2 1.1(4) . . . . ?
C21 C22 C25 O4 153.5(2) . . . . ?
C21 C22 C25 C26 -20.6(3) . . . . ?
C21 C22 C23 C24 1.5(3) . . . . ?
C21 C20 C19 F2 179.7(2) . . . . ?
C21 C20 C19 C24 1.4(4) . . . . ?
C33 C32 C31 N4 -167.84(17) . . . . ?
C33 C32 C31 C36 10.4(3) . . . . ?
C33 C34 C35 C36 47.6(3) . . . . ?
C31 N4 C27 N3 -177.30(18) . . . . ?
C31 N4 C27 C26 -1.5(2) . . . . ?
C31 N4 C30 C29 148.0(2) . . . . ?
C31 C32 C33 O3 161.6(2) . . . . ?
C31 C32 C33 C34 -15.5(3) . . . . ?
C31 C36 C35 C34 -49.9(3) . . . . ?
C3 C4 C7 O1 -144.1(2) . . . . ?
C3 C4 C7 C8 32.5(3) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
C3 C2 C1 F1 178.8(2) . . . . ?
C3 C2 C1 C6 -1.8(4) . . . . ?
C23 C22 C25 O4 -20.7(3) . . . . ?
C23 C22 C25 C26 165.25(19) . . . . ?
C23 C22 C21 C20 -1.2(3) . . . . ?
C13 C12 C11 C10 -50.2(3) . . . . ?
C30 N4 C27 N3 2.3(3) . . . . ?
C30 N4 C27 C26 178.07(18) . . . . ?
C30 N4 C31 C32 -178.90(19) . . . . ?
C30 N4 C31 C36 2.9(3) . . . . ?
C30 C29 C28 N3 -52.1(3) . . . . ?
C18 N2 C14 C9 -178.33(18) . . . . ?
C18 N2 C14 C13 -0.4(3) . . . . ?
C18 N2 C15 N1 -5.1(3) . . . . ?
C18 N2 C15 C8 179.28(17) . . . . ?
C20 C19 C24 C23 -1.1(4) . . . . ?
C28 N3 C27 N4 2.5(3) . . . . ?
C28 N3 C27 C26 -172.3(2) . . . . ?
C16 N1 C15 N2 4.0(3) . . . . ?
C16 N1 C15 C8 178.5(2) . . . . ?

####################################################################### 
# 
# 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 2373954'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Yunnan University
China
;
_audit_update_record             
;
2024-07-27 deposited with the CCDC.	2024-09-10 downloaded from the CCDC.
;
_audit_creation_date             2024-02-27
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2024,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_diffrn_source_power             0.07
_chemical_name_common            ?
_chemical_formula_sum            'C24 H21 F N2 O2'
_chemical_formula_moiety         'C24 H21 F N2 O2'
_chemical_formula_weight         388.43
_exptl_crystal_colour_primary    yellow
_chemical_melting_point          ?
_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, All N(H) groups
2. Restrained distances
 C25-C26 \\sim C25-C26A
 with sigma of 0.02
 C26-C27 \\sim C26A-C27
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N3, N4, C25, C26, C27, C28, C26A
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0001
4. Others
 Sof(H25C)=Sof(H25D)=Sof(H27C)=Sof(H27D)=Sof(C26A)=Sof(H26C)=Sof(H26D)=1-FVAR(1)
 Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H27A)=Sof(H27B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C34(H34)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C9(H9A,H9B), C10(H10A,H10B), C25(H25A,
 H25B), C25(H25C,H25D), C26(H26A,H26B), C27(H27A,H27B), C27(H27C,H27D),
 C33(H33A,H33B), C35(H35A,H35B), C26A(H26C,H26D)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21),
 C23(H23), C24(H24), N4(H4), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41),
 C43(H43), C44(H44), C46(H46), C47(H47)
5.d Fitted hexagon refined as free rotating group:
 C36(C37,C38,C39,C40,C41)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_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.
;

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                   14.4294(6)
_cell_length_b                   18.3423(10)
_cell_length_c                   14.5578(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.1700(10)
_cell_angle_gamma                90
_cell_volume                     3853.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298.15
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      25.40
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7124
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1354 before and 0.0688 after correction.
The Ratio of minimum to maximum transmission is 0.9553.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.982
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      298.15
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            85595
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.1034
_diffrn_reflns_theta_min         2.221
_diffrn_reflns_theta_max         28.396
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9588
_reflns_number_gt                5552
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+3.1389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         9588
_refine_ls_number_parameters     521
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0845
_refine_ls_wR_factor_ref         0.1864
_refine_ls_wR_factor_gt          0.1539
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 0.55748(14) 0.22036(13) 1.18664(14) 0.0904(7) Uani 1 1 d . . . . .
O1 O 0.16928(14) 0.11201(15) 1.06362(13) 0.0706(7) Uani 1 1 d . . . . .
O2 O 0.21642(17) 0.11152(19) 0.59752(15) 0.1001(10) Uani 1 1 d . . . . .
N1 N 0.04914(16) 0.09838(15) 0.91792(16) 0.0578(7) Uani 1 1 d . . . . .
H1 H 0.047012 0.101628 0.976810 0.069 Uiso 1 1 calc R U . . .
N2 N 0.13458(15) 0.11040(13) 0.78309(14) 0.0460(6) Uani 1 1 d . . . . .
C1 C -0.0338(2) 0.0765(2) 0.8678(2) 0.0675(9) Uani 1 1 d . . . . .
H1A H -0.088441 0.092920 0.900482 0.081 Uiso 1 1 calc R U . . .
H1B H -0.036234 0.023732 0.863580 0.081 Uiso 1 1 calc R U . . .
C2 C -0.0328(2) 0.1089(2) 0.7730(2) 0.0692(10) Uani 1 1 d . . . . .
H2A H -0.040896 0.161306 0.777600 0.083 Uiso 1 1 calc R U . . .
H2B H -0.084449 0.089522 0.737988 0.083 Uiso 1 1 calc R U . . .
C3 C 0.05590(19) 0.09311(18) 0.72288(19) 0.0558(8) Uani 1 1 d . . . . .
H3A H 0.057971 0.042084 0.705512 0.067 Uiso 1 1 calc R U . . .
H3B H 0.059056 0.122293 0.667413 0.067 Uiso 1 1 calc R U . . .
C4 C 0.12782(18) 0.11347(16) 0.87519(18) 0.0450(6) Uani 1 1 d . . . . .
C5 C 0.21594(17) 0.13389(15) 0.91303(17) 0.0424(6) Uani 1 1 d . . . . .
C6 C 0.27656(17) 0.14194(15) 0.83626(16) 0.0411(6) Uani 1 1 d . . . . .
C7 C 0.22603(18) 0.12750(16) 0.75806(17) 0.0453(6) Uani 1 1 d . . . . .
C8 C 0.2623(2) 0.12653(19) 0.66592(19) 0.0602(8) Uani 1 1 d . . . . .
C9 C 0.3631(2) 0.1464(2) 0.65950(19) 0.0636(9) Uani 1 1 d . . . . .
H9A H 0.368383 0.198733 0.651713 0.076 Uiso 1 1 calc R U . . .
H9B H 0.389195 0.123413 0.605411 0.076 Uiso 1 1 calc R U . . .
C10 C 0.37832(17) 0.15815(16) 0.82997(17) 0.0444(6) Uani 1 1 d . . . . .
H10A H 0.409782 0.139072 0.883814 0.053 Uiso 1 1 calc R U . . .
H10B H 0.387756 0.210492 0.828386 0.053 Uiso 1 1 calc R U . . .
C11 C 0.41943(19) 0.12360(17) 0.74326(18) 0.0496(7) Uani 1 1 d . . . . .
H11 H 0.412471 0.070685 0.749561 0.060 Uiso 1 1 calc R U . . .
C12 C 0.5220(2) 0.13882(17) 0.73311(18) 0.0511(7) Uani 1 1 d . . . . .
C13 C 0.5553(2) 0.2027(2) 0.6963(3) 0.0733(10) Uani 1 1 d . . . . .
H13 H 0.513791 0.238092 0.676081 0.088 Uiso 1 1 calc R U . . .
C14 C 0.6498(2) 0.2152(2) 0.6888(3) 0.0813(11) Uani 1 1 d . . . . .
H14 H 0.670692 0.258708 0.663467 0.098 Uiso 1 1 calc R U . . .
C15 C 0.7122(2) 0.1648(2) 0.7180(2) 0.0758(10) Uani 1 1 d . . . . .
H15 H 0.775444 0.173740 0.713360 0.091 Uiso 1 1 calc R U . . .
C16 C 0.6807(3) 0.1011(2) 0.7541(3) 0.0846(12) Uani 1 1 d . . . . .
H16 H 0.722621 0.066107 0.774367 0.102 Uiso 1 1 calc R U . . .
C17 C 0.5867(2) 0.0882(2) 0.7609(2) 0.0685(9) Uani 1 1 d . . . . .
H17 H 0.566549 0.043970 0.784882 0.082 Uiso 1 1 calc R U . . .
C18 C 0.23086(19) 0.13278(17) 1.01081(18) 0.0480(7) Uani 1 1 d . . . . .
C19 C 0.32090(18) 0.15548(16) 1.05296(17) 0.0445(6) Uani 1 1 d . . . . .
C20 C 0.3615(2) 0.22192(17) 1.0334(2) 0.0558(8) Uani 1 1 d . . . . .
H20 H 0.335229 0.251918 0.988925 0.067 Uiso 1 1 calc R U . . .
C21 C 0.4407(2) 0.24447(19) 1.0791(2) 0.0647(9) Uani 1 1 d . . . . .
H21 H 0.467345 0.289591 1.066790 0.078 Uiso 1 1 calc R U . . .
C22 C 0.4787(2) 0.1985(2) 1.1429(2) 0.0620(9) Uani 1 1 d . . . . .
C23 C 0.4408(2) 0.1329(2) 1.1646(2) 0.0634(9) Uani 1 1 d . . . . .
H23 H 0.467957 0.103143 1.208784 0.076 Uiso 1 1 calc R U . . .
C24 C 0.3612(2) 0.11157(18) 1.11972(19) 0.0563(8) Uani 1 1 d . . . . .
H24 H 0.334045 0.067088 1.134316 0.068 Uiso 1 1 calc R U . . .
F2 F 0.04017(12) 0.41940(13) 0.46824(14) 0.0873(7) Uani 1 1 d . . . . .
O3 O 0.38290(15) 0.41810(14) 1.05118(13) 0.0679(6) Uani 1 1 d . . . . .
O4 O 0.44910(14) 0.36122(14) 0.59013(13) 0.0695(7) Uani 1 1 d . . . . .
N3 N 0.47313(15) 0.39948(13) 0.87026(15) 0.0483(5) Uani 1 1 d . . . . .
N4 N 0.56670(15) 0.39060(15) 0.73996(16) 0.0573(6) Uani 1 1 d . . . . .
H4 H 0.571173 0.385625 0.681401 0.069 Uiso 1 1 calc R U . . .
C25 C 0.55199(19) 0.4070(2) 0.9334(2) 0.0662(9) Uani 1 1 d D . . . .
H25A H 0.563612 0.458111 0.946042 0.079 Uiso 0.698(10) 1 calc R U P A 1
H25B H 0.538762 0.382581 0.990943 0.079 Uiso 0.698(10) 1 calc R U P A 1
H25C H 0.562999 0.361112 0.964650 0.079 Uiso 0.302(10) 1 calc R U P A 2
H25D H 0.538337 0.443758 0.979267 0.079 Uiso 0.302(10) 1 calc R U P A 2
C26 C 0.6327(4) 0.3742(6) 0.8900(3) 0.085(2) Uani 0.698(10) 1 d D . P A 1
H26A H 0.625079 0.321674 0.890338 0.102 Uiso 0.698(10) 1 calc R U P A 1
H26B H 0.686951 0.385505 0.926862 0.102 Uiso 0.698(10) 1 calc R U P A 1
C27 C 0.6502(2) 0.3979(3) 0.7947(2) 0.0808(11) Uani 1 1 d D . . . .
H27A H 0.670401 0.448351 0.794501 0.097 Uiso 0.698(10) 1 calc R U P A 1
H27B H 0.699182 0.368442 0.768257 0.097 Uiso 0.698(10) 1 calc R U P A 1
H27C H 0.676113 0.349641 0.803885 0.097 Uiso 0.302(10) 1 calc R U P A 2
H27D H 0.694878 0.425756 0.759479 0.097 Uiso 0.302(10) 1 calc R U P A 2
C28 C 0.48327(18) 0.39143(16) 0.77851(17) 0.0454(6) Uani 1 1 d . . . . .
C29 C 0.39388(17) 0.38680(16) 0.73697(17) 0.0443(6) Uani 1 1 d . . . . .
C30 C 0.32917(18) 0.39252(16) 0.81032(17) 0.0448(6) Uani 1 1 d . . . . .
C31 C 0.37820(18) 0.40047(16) 0.89047(17) 0.0464(7) Uani 1 1 d . . . . .
C32 C 0.3380(2) 0.41115(17) 0.97983(18) 0.0517(7) Uani 1 1 d . . . . .
C33 C 0.2341(2) 0.4137(2) 0.97968(19) 0.0595(8) Uani 1 1 d . . . . .
H33A H 0.214563 0.464136 0.973735 0.071 Uiso 1 1 calc R U . . .
H33B H 0.211916 0.395990 1.038417 0.071 Uiso 1 1 calc R U . . .
C34 C 0.18914(19) 0.36999(19) 0.90458(19) 0.0572(8) Uani 1 1 d . . . . .
H34 H 0.207894 0.319420 0.915870 0.069 Uiso 1 1 calc R U . . .
C35 C 0.22536(18) 0.38811(19) 0.81058(18) 0.0532(8) Uani 1 1 d . . . . .
H35A H 0.205351 0.351004 0.767384 0.064 Uiso 1 1 calc R U . . .
H35B H 0.199748 0.434414 0.790738 0.064 Uiso 1 1 calc R U . . .
C36 C 0.08438(11) 0.36962(13) 0.90818(14) 0.0549(8) Uani 1 1 d G . . . .
C37 C 0.03131(19) 0.43268(11) 0.90207(15) 0.0803(11) Uani 1 1 d G . . . .
H37 H 0.060132 0.477829 0.896689 0.096 Uiso 1 1 calc R U . . .
C38 C -0.06483(18) 0.42828(18) 0.90399(16) 0.1038(17) Uani 1 1 d G . . . .
H38 H -0.100336 0.470476 0.899902 0.125 Uiso 1 1 calc R U . . .
C39 C -0.10790(11) 0.3608(2) 0.91203(17) 0.115(2) Uani 1 1 d G . . . .
H39 H -0.172229 0.357860 0.913322 0.138 Uiso 1 1 calc R U . . .
C40 C -0.05484(17) 0.29774(17) 0.91815(18) 0.1085(17) Uani 1 1 d G . . . .
H40 H -0.083655 0.252596 0.923529 0.130 Uiso 1 1 calc R U . . .
C41 C 0.04131(16) 0.30214(11) 0.91622(16) 0.0754(10) Uani 1 1 d G . . . .
H41 H 0.076813 0.259947 0.920315 0.091 Uiso 1 1 calc R U . . .
C42 C 0.28976(18) 0.38732(16) 0.59587(17) 0.0430(6) Uani 1 1 d . . . . .
C43 C 0.2544(2) 0.33481(19) 0.5366(2) 0.0615(8) Uani 1 1 d . . . . .
H43 H 0.287574 0.292236 0.525716 0.074 Uiso 1 1 calc R U . . .
C44 C 0.1698(2) 0.3458(2) 0.4938(2) 0.0700(10) Uani 1 1 d . . . . .
H44 H 0.145130 0.310761 0.454622 0.084 Uiso 1 1 calc R U . . .
C45 C 0.12340(19) 0.4090(2) 0.5102(2) 0.0573(8) Uani 1 1 d . . . . .
C46 C 0.15618(19) 0.46224(18) 0.56599(19) 0.0537(7) Uani 1 1 d . . . . .
H46 H 0.123328 0.505299 0.574691 0.064 Uiso 1 1 calc R U . . .
C47 C 0.23996(18) 0.45046(16) 0.60944(18) 0.0478(7) Uani 1 1 d . . . . .
H47 H 0.263351 0.485968 0.648783 0.057 Uiso 1 1 calc R U . . .
C48 C 0.38254(18) 0.37708(17) 0.63972(18) 0.0473(7) Uani 1 1 d . . . . .
C26A C 0.6412(7) 0.4298(11) 0.8775(7) 0.078(3) Uani 0.302(10) 1 d D . P A 2
H26C H 0.640266 0.482201 0.868949 0.094 Uiso 0.302(10) 1 calc R U P A 2
H26D H 0.695500 0.418099 0.914137 0.094 Uiso 0.302(10) 1 calc R U P A 2


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 C22 1.362(3) . ?
O1 C18 1.237(3) . ?
O2 C8 1.225(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.456(4) . ?
N1 C4 1.325(3) . ?
N2 C3 1.467(3) . ?
N2 C4 1.346(3) . ?
N2 C7 1.405(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.503(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.503(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.434(4) . ?
C5 C6 1.429(4) . ?
C5 C18 1.439(3) . ?
C6 C7 1.376(3) . ?
C6 C10 1.501(4) . ?
C7 C8 1.441(4) . ?
C8 C9 1.503(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C11 1.522(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.533(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.513(4) . ?
C12 C13 1.376(4) . ?
C12 C17 1.377(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.357(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.361(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.494(4) . ?
C19 C20 1.382(4) . ?
C19 C24 1.389(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.368(4) . ?
C22 C23 1.359(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(4) . ?
C24 H24 0.9300 . ?
F2 C45 1.360(3) . ?
O3 C32 1.229(3) . ?
O4 C48 1.238(3) . ?
N3 C25 1.467(3) . ?
N3 C28 1.352(3) . ?
N3 C31 1.402(3) . ?
N4 H4 0.8600 . ?
N4 C27 1.449(4) . ?
N4 C28 1.330(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C25 H25D 0.9700 . ?
C25 C26 1.456(6) . ?
C25 C26A 1.581(11) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.476(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
C27 H27D 0.9700 . ?
C27 C26A 1.346(11) . ?
C28 C29 1.425(3) . ?
C29 C30 1.424(4) . ?
C29 C48 1.436(4) . ?
C30 C31 1.371(3) . ?
C30 C35 1.500(4) . ?
C31 C32 1.439(4) . ?
C32 C33 1.501(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.502(4) . ?
C34 H34 0.9800 . ?
C34 C35 1.503(4) . ?
C34 C36 1.513(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.3900 . ?
C36 C41 1.3900 . ?
C37 H37 0.9300 . ?
C37 C38 1.3900 . ?
C38 H38 0.9300 . ?
C38 C39 1.3900 . ?
C39 H39 0.9300 . ?
C39 C40 1.3900 . ?
C40 H40 0.9300 . ?
C40 C41 1.3900 . ?
C41 H41 0.9300 . ?
C42 C43 1.389(4) . ?
C42 C47 1.377(4) . ?
C42 C48 1.493(4) . ?
C43 H43 0.9300 . ?
C43 C44 1.384(4) . ?
C44 H44 0.9300 . ?
C44 C45 1.359(5) . ?
C45 C46 1.354(4) . ?
C46 H46 0.9300 . ?
C46 C47 1.380(4) . ?
C47 H47 0.9300 . ?
C26A H26C 0.9700 . ?
C26A H26D 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
C1 N1 H1 119.1 . . ?
C4 N1 H1 119.1 . . ?
C4 N1 C1 121.8(2) . . ?
C4 N2 C3 123.1(2) . . ?
C4 N2 C7 108.7(2) . . ?
C7 N2 C3 128.2(2) . . ?
N1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
N1 C1 C2 109.9(3) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C1 C2 C3 112.3(3) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
N2 C3 C2 109.1(2) . . ?
N2 C3 H3A 109.9 . . ?
N2 C3 H3B 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N1 C4 N2 121.6(2) . . ?
N1 C4 C5 129.3(2) . . ?
N2 C4 C5 109.1(2) . . ?
C4 C5 C18 120.4(2) . . ?
C6 C5 C4 105.7(2) . . ?
C6 C5 C18 133.2(2) . . ?
C5 C6 C10 132.0(2) . . ?
C7 C6 C5 107.6(2) . . ?
C7 C6 C10 120.3(2) . . ?
N2 C7 C8 125.6(2) . . ?
C6 C7 N2 108.9(2) . . ?
C6 C7 C8 125.4(3) . . ?
O2 C8 C7 124.3(3) . . ?
O2 C8 C9 121.6(3) . . ?
C7 C8 C9 114.1(2) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C8 C9 C11 113.5(2) . . ?
H9A C9 H9B 107.7 . . ?
C11 C9 H9A 108.9 . . ?
C11 C9 H9B 108.9 . . ?
C6 C10 H10A 109.6 . . ?
C6 C10 H10B 109.6 . . ?
C6 C10 C11 110.4(2) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C11 C10 109.8(2) . . ?
C9 C11 H11 107.0 . . ?
C10 C11 H11 107.0 . . ?
C12 C11 C9 113.0(2) . . ?
C12 C11 C10 112.6(2) . . ?
C12 C11 H11 107.0 . . ?
C13 C12 C11 122.5(3) . . ?
C13 C12 C17 116.8(3) . . ?
C17 C12 C11 120.6(3) . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 118.9(3) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.3(4) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 121.9(3) . . ?
C12 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
O1 C18 C5 120.9(2) . . ?
O1 C18 C19 117.1(2) . . ?
C5 C18 C19 122.0(2) . . ?
C20 C19 C18 122.0(2) . . ?
C20 C19 C24 118.6(3) . . ?
C24 C19 C18 119.2(3) . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 121.0 . . ?
C22 C21 C20 118.1(3) . . ?
C22 C21 H21 121.0 . . ?
F1 C22 C21 117.9(3) . . ?
C23 C22 F1 119.2(3) . . ?
C23 C22 C21 122.9(3) . . ?
C22 C23 H23 120.7 . . ?
C22 C23 C24 118.5(3) . . ?
C24 C23 H23 120.7 . . ?
C19 C24 H24 119.5 . . ?
C23 C24 C19 120.9(3) . . ?
C23 C24 H24 119.5 . . ?
C28 N3 C25 122.9(2) . . ?
C28 N3 C31 108.5(2) . . ?
C31 N3 C25 128.6(2) . . ?
C27 N4 H4 119.4 . . ?
C28 N4 H4 119.4 . . ?
C28 N4 C27 121.3(2) . . ?
N3 C25 H25A 110.1 . . ?
N3 C25 H25B 110.1 . . ?
N3 C25 H25C 109.8 . . ?
N3 C25 H25D 109.8 . . ?
N3 C25 C26A 109.5(5) . . ?
H25A C25 H25B 108.4 . . ?
H25C C25 H25D 108.2 . . ?
C26 C25 N3 108.0(3) . . ?
C26 C25 H25A 110.1 . . ?
C26 C25 H25B 110.1 . . ?
C26A C25 H25C 109.8 . . ?
C26A C25 H25D 109.8 . . ?
C25 C26 H26A 108.5 . . ?
C25 C26 H26B 108.5 . . ?
C25 C26 C27 115.2(5) . . ?
H26A C26 H26B 107.5 . . ?
C27 C26 H26A 108.5 . . ?
C27 C26 H26B 108.5 . . ?
N4 C27 C26 110.2(3) . . ?
N4 C27 H27A 109.6 . . ?
N4 C27 H27B 109.6 . . ?
N4 C27 H27C 108.1 . . ?
N4 C27 H27D 108.1 . . ?
C26 C27 H27A 109.6 . . ?
C26 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
H27C C27 H27D 107.3 . . ?
C26A C27 N4 116.8(6) . . ?
C26A C27 H27C 108.1 . . ?
C26A C27 H27D 108.1 . . ?
N3 C28 C29 109.0(2) . . ?
N4 C28 N3 121.3(2) . . ?
N4 C28 C29 129.7(2) . . ?
C28 C29 C48 121.7(2) . . ?
C30 C29 C28 105.8(2) . . ?
C30 C29 C48 132.5(2) . . ?
C29 C30 C35 130.9(2) . . ?
C31 C30 C29 108.0(2) . . ?
C31 C30 C35 121.1(2) . . ?
N3 C31 C32 126.0(2) . . ?
C30 C31 N3 108.8(2) . . ?
C30 C31 C32 125.2(3) . . ?
O3 C32 C31 124.4(3) . . ?
O3 C32 C33 121.5(3) . . ?
C31 C32 C33 114.1(2) . . ?
C32 C33 H33A 108.7 . . ?
C32 C33 H33B 108.7 . . ?
C32 C33 C34 114.4(2) . . ?
H33A C33 H33B 107.6 . . ?
C34 C33 H33A 108.7 . . ?
C34 C33 H33B 108.7 . . ?
C33 C34 H34 105.4 . . ?
C33 C34 C35 113.2(3) . . ?
C33 C34 C36 114.0(2) . . ?
C35 C34 H34 105.4 . . ?
C35 C34 C36 112.5(2) . . ?
C36 C34 H34 105.4 . . ?
C30 C35 C34 111.4(2) . . ?
C30 C35 H35A 109.4 . . ?
C30 C35 H35B 109.4 . . ?
C34 C35 H35A 109.4 . . ?
C34 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
C37 C36 C34 123.0(2) . . ?
C37 C36 C41 120.0 . . ?
C41 C36 C34 117.0(2) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 120.0 . . ?
C38 C37 H37 120.0 . . ?
C37 C38 H38 120.0 . . ?
C39 C38 C37 120.0 . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 120.0 . . ?
C38 C39 C40 120.0 . . ?
C40 C39 H39 120.0 . . ?
C39 C40 H40 120.0 . . ?
C39 C40 C41 120.0 . . ?
C41 C40 H40 120.0 . . ?
C36 C41 H41 120.0 . . ?
C40 C41 C36 120.0 . . ?
C40 C41 H41 120.0 . . ?
C43 C42 C48 120.4(3) . . ?
C47 C42 C43 118.8(2) . . ?
C47 C42 C48 120.8(2) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 C42 120.0(3) . . ?
C44 C43 H43 120.0 . . ?
C43 C44 H44 120.7 . . ?
C45 C44 C43 118.6(3) . . ?
C45 C44 H44 120.7 . . ?
F2 C45 C44 118.4(3) . . ?
C46 C45 F2 118.3(3) . . ?
C46 C45 C44 123.3(3) . . ?
C45 C46 H46 121.1 . . ?
C45 C46 C47 117.8(3) . . ?
C47 C46 H46 121.1 . . ?
C42 C47 C46 121.5(3) . . ?
C42 C47 H47 119.2 . . ?
C46 C47 H47 119.2 . . ?
O4 C48 C29 121.2(2) . . ?
O4 C48 C42 118.4(2) . . ?
C29 C48 C42 120.3(2) . . ?
C25 C26A H26C 108.5 . . ?
C25 C26A H26D 108.5 . . ?
C27 C26A C25 115.3(9) . . ?
C27 C26A H26C 108.5 . . ?
C27 C26A H26D 108.5 . . ?
H26C C26A H26D 107.5 . . ?

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
F1 C22 C23 C24 -180.0(3) . . . . ?
O1 C18 C19 C20 -127.9(3) . . . . ?
O1 C18 C19 C24 46.4(4) . . . . ?
O2 C8 C9 C11 -148.6(4) . . . . ?
N1 C1 C2 C3 52.3(4) . . . . ?
N1 C4 C5 C6 178.7(3) . . . . ?
N1 C4 C5 C18 6.8(5) . . . . ?
N2 C4 C5 C6 -0.7(3) . . . . ?
N2 C4 C5 C18 -172.6(3) . . . . ?
N2 C7 C8 O2 1.2(6) . . . . ?
N2 C7 C8 C9 -179.3(3) . . . . ?
C1 N1 C4 N2 1.1(5) . . . . ?
C1 N1 C4 C5 -178.3(3) . . . . ?
C1 C2 C3 N2 -48.7(4) . . . . ?
C3 N2 C4 N1 2.4(4) . . . . ?
C3 N2 C4 C5 -178.2(3) . . . . ?
C3 N2 C7 C6 178.4(3) . . . . ?
C3 N2 C7 C8 -4.5(5) . . . . ?
C4 N1 C1 C2 -28.4(4) . . . . ?
C4 N2 C3 C2 22.0(4) . . . . ?
C4 N2 C7 C6 -0.5(3) . . . . ?
C4 N2 C7 C8 176.7(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C4 C5 C6 C10 -175.9(3) . . . . ?
C4 C5 C18 O1 2.4(4) . . . . ?
C4 C5 C18 C19 -178.4(3) . . . . ?
C5 C6 C7 N2 0.0(3) . . . . ?
C5 C6 C7 C8 -177.2(3) . . . . ?
C5 C6 C10 C11 150.6(3) . . . . ?
C5 C18 C19 C20 52.9(4) . . . . ?
C5 C18 C19 C24 -132.8(3) . . . . ?
C6 C5 C18 O1 -166.9(3) . . . . ?
C6 C5 C18 C19 12.3(5) . . . . ?
C6 C7 C8 O2 177.9(3) . . . . ?
C6 C7 C8 C9 -2.6(5) . . . . ?
C6 C10 C11 C9 52.6(3) . . . . ?
C6 C10 C11 C12 179.5(2) . . . . ?
C7 N2 C3 C2 -156.7(3) . . . . ?
C7 N2 C4 N1 -178.8(3) . . . . ?
C7 N2 C4 C5 0.7(3) . . . . ?
C7 C6 C10 C11 -25.4(4) . . . . ?
C7 C8 C9 C11 31.9(4) . . . . ?
C8 C9 C11 C10 -57.5(4) . . . . ?
C8 C9 C11 C12 175.8(3) . . . . ?
C9 C11 C12 C13 42.7(4) . . . . ?
C9 C11 C12 C17 -137.2(3) . . . . ?
C10 C6 C7 N2 176.9(2) . . . . ?
C10 C6 C7 C8 -0.3(5) . . . . ?
C10 C11 C12 C13 -82.5(4) . . . . ?
C10 C11 C12 C17 97.6(3) . . . . ?
C11 C12 C13 C14 179.4(3) . . . . ?
C11 C12 C17 C16 -178.7(3) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
C13 C12 C17 C16 1.3(5) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C12 -1.0(6) . . . . ?
C17 C12 C13 C14 -0.7(5) . . . . ?
C18 C5 C6 C7 170.8(3) . . . . ?
C18 C5 C6 C10 -5.6(5) . . . . ?
C18 C19 C20 C21 174.4(3) . . . . ?
C18 C19 C24 C23 -175.6(3) . . . . ?
C19 C20 C21 C22 1.3(5) . . . . ?
C20 C19 C24 C23 -1.1(4) . . . . ?
C20 C21 C22 F1 179.0(3) . . . . ?
C20 C21 C22 C23 -1.7(5) . . . . ?
C21 C22 C23 C24 0.7(5) . . . . ?
C22 C23 C24 C19 0.7(5) . . . . ?
C24 C19 C20 C21 0.1(4) . . . . ?
F2 C45 C46 C47 178.9(3) . . . . ?
O3 C32 C33 C34 -151.1(3) . . . . ?
N3 C25 C26 C27 49.6(8) . . . . ?
N3 C25 C26A C27 -38.4(16) . . . . ?
N3 C28 C29 C30 -0.1(3) . . . . ?
N3 C28 C29 C48 -179.2(3) . . . . ?
N3 C31 C32 O3 -2.9(5) . . . . ?
N3 C31 C32 C33 176.7(3) . . . . ?
N4 C27 C26A C25 40.8(17) . . . . ?
N4 C28 C29 C30 -178.3(3) . . . . ?
N4 C28 C29 C48 2.6(5) . . . . ?
C25 N3 C28 N4 -0.6(5) . . . . ?
C25 N3 C28 C29 -179.1(3) . . . . ?
C25 N3 C31 C30 179.2(3) . . . . ?
C25 N3 C31 C32 1.6(5) . . . . ?
C25 C26 C27 N4 -51.0(8) . . . . ?
C27 N4 C28 N3 0.3(5) . . . . ?
C27 N4 C28 C29 178.4(3) . . . . ?
C28 N3 C25 C26 -23.9(6) . . . . ?
C28 N3 C25 C26A 18.3(9) . . . . ?
C28 N3 C31 C30 0.3(3) . . . . ?
C28 N3 C31 C32 -177.2(3) . . . . ?
C28 N4 C27 C26 24.4(6) . . . . ?
C28 N4 C27 C26A -22.2(11) . . . . ?
C28 C29 C30 C31 0.3(3) . . . . ?
C28 C29 C30 C35 -177.0(3) . . . . ?
C28 C29 C48 O4 11.2(5) . . . . ?
C28 C29 C48 C42 -167.7(3) . . . . ?
C29 C30 C31 N3 -0.4(3) . . . . ?
C29 C30 C31 C32 177.2(3) . . . . ?
C29 C30 C35 C34 159.2(3) . . . . ?
C30 C29 C48 O4 -167.6(3) . . . . ?
C30 C29 C48 C42 13.5(5) . . . . ?
C30 C31 C32 O3 179.9(3) . . . . ?
C30 C31 C32 C33 -0.5(4) . . . . ?
C31 N3 C25 C26 157.4(5) . . . . ?
C31 N3 C25 C26A -160.4(8) . . . . ?
C31 N3 C28 N4 178.3(3) . . . . ?
C31 N3 C28 C29 -0.2(3) . . . . ?
C31 C30 C35 C34 -17.8(4) . . . . ?
C31 C32 C33 C34 29.2(4) . . . . ?
C32 C33 C34 C35 -52.9(4) . . . . ?
C32 C33 C34 C36 176.8(2) . . . . ?
C33 C34 C35 C30 45.6(4) . . . . ?
C33 C34 C36 C37 60.0(3) . . . . ?
C33 C34 C36 C41 -121.2(3) . . . . ?
C34 C36 C37 C38 178.7(2) . . . . ?
C34 C36 C41 C40 -178.8(2) . . . . ?
C35 C30 C31 N3 177.2(3) . . . . ?
C35 C30 C31 C32 -5.2(5) . . . . ?
C35 C34 C36 C37 -70.6(3) . . . . ?
C35 C34 C36 C41 108.1(3) . . . . ?
C36 C34 C35 C30 176.6(3) . . . . ?
C36 C37 C38 C39 0.0 . . . . ?
C37 C36 C41 C40 0.0 . . . . ?
C37 C38 C39 C40 0.0 . . . . ?
C38 C39 C40 C41 0.0 . . . . ?
C39 C40 C41 C36 0.0 . . . . ?
C41 C36 C37 C38 0.0 . . . . ?
C42 C43 C44 C45 0.8(5) . . . . ?
C43 C42 C47 C46 0.3(4) . . . . ?
C43 C42 C48 O4 50.6(4) . . . . ?
C43 C42 C48 C29 -130.5(3) . . . . ?
C43 C44 C45 F2 -179.8(3) . . . . ?
C43 C44 C45 C46 0.6(5) . . . . ?
C44 C45 C46 C47 -1.4(5) . . . . ?
C45 C46 C47 C42 1.0(4) . . . . ?
C47 C42 C43 C44 -1.2(5) . . . . ?
C47 C42 C48 O4 -125.9(3) . . . . ?
C47 C42 C48 C29 53.0(4) . . . . ?
C48 C29 C30 C31 179.2(3) . . . . ?
C48 C29 C30 C35 2.0(6) . . . . ?
C48 C42 C43 C44 -177.8(3) . . . . ?
C48 C42 C47 C46 176.9(3) . . . . ?

