# 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_Y
_database_code_depnum_ccdc_archive 'CCDC 2341706'
_audit_update_record             
;
2024-03-20 deposited with the CCDC.	2024-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 F3 N5 O'
_chemical_formula_weight         401.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.4542(7)
_cell_length_b                   19.2551(10)
_cell_length_c                   7.9463(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.380(2)
_cell_angle_gamma                90
_cell_volume                     1994.09(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35677
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.630
_diffrn_reflns_theta_max         25.649
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3771
_reflns_number_gt                2950
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0555P)²+0.7710P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3771
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.87583(9) 0.00305(8) 0.87119(17) 0.0614(4) Uani 1 1 d . . . . .
N1 N 0.67559(12) 0.00169(9) 0.48977(19) 0.0539(4) Uani 1 1 d . . . . .
N2 N 0.67927(13) 0.04834(10) 0.3843(2) 0.0607(4) Uani 1 1 d . . . . .
N3 N 0.67719(18) 0.08587(13) 0.2748(2) 0.0910(7) Uani 1 1 d . . . . .
N4 N 0.86805(10) 0.06033(8) 0.61223(18) 0.0475(4) Uani 1 1 d . . . . .
N5 N 1.03790(11) 0.06261(9) 0.7936(2) 0.0551(4) Uani 1 1 d . . . . .
H5N H 1.0287 0.0424 0.8836 0.066 Uiso 1 1 d R U . . .
C1 C 0.82859(12) 0.02677(9) 0.7311(2) 0.0422(4) Uani 1 1 d . . . . .
C2 C 0.70945(12) 0.02220(9) 0.6783(2) 0.0425(4) Uani 1 1 d . . . . .
C3 C 0.68939(17) -0.10513(11) 0.7346(3) 0.0636(5) Uani 1 1 d . . . . .
H3 H 0.7214 -0.1144 0.6459 0.076 Uiso 1 1 calc R U . . .
C4 C 0.6589(2) -0.15984(12) 0.8236(3) 0.0786(7) Uani 1 1 d . . . . .
H4 H 0.6704 -0.2053 0.7941 0.094 Uiso 1 1 calc R U . . .
C5 C 0.61180(17) -0.14703(13) 0.9550(3) 0.0742(7) Uani 1 1 d . . . . .
H5 H 0.5907 -0.1837 1.0141 0.089 Uiso 1 1 calc R U . . .
C6 C 0.59614(16) -0.08020(13) 0.9984(3) 0.0706(6) Uani 1 1 d . . . . .
H6 H 0.5650 -0.0713 1.0884 0.085 Uiso 1 1 calc R U . . .
C7 C 0.62615(14) -0.02521(11) 0.9095(3) 0.0579(5) Uani 1 1 d . . . . .
H7 H 0.6147 0.0202 0.9401 0.069 Uiso 1 1 calc R U . . .
C8 C 0.67299(12) -0.03721(9) 0.7758(2) 0.0456(4) Uani 1 1 d . . . . .
C9 C 0.56364(14) 0.10883(11) 0.6278(3) 0.0567(5) Uani 1 1 d . . . . .
H9 H 0.5239 0.0772 0.5513 0.068 Uiso 1 1 calc R U . . .
C10 C 0.52159(17) 0.17160(12) 0.6585(3) 0.0693(6) Uani 1 1 d . . . . .
H10 H 0.4540 0.1818 0.6021 0.083 Uiso 1 1 calc R U . . .
C11 C 0.57797(19) 0.21868(12) 0.7701(3) 0.0754(6) Uani 1 1 d . . . . .
H11 H 0.5494 0.2610 0.7892 0.090 Uiso 1 1 calc R U . . .
C12 C 0.6772(2) 0.20317(13) 0.8542(4) 0.0864(8) Uani 1 1 d . . . . .
H12 H 0.7159 0.2348 0.9319 0.104 Uiso 1 1 calc R U . . .
C13 C 0.72022(16) 0.14041(12) 0.8238(3) 0.0700(6) Uani 1 1 d . . . . .
H13 H 0.7878 0.1305 0.8813 0.084 Uiso 1 1 calc R U . . .
C14 C 0.66446(12) 0.09252(9) 0.7099(2) 0.0446(4) Uani 1 1 d . . . . .
C15 C 0.96652(13) 0.07594(9) 0.6532(2) 0.0458(4) Uani 1 1 d . . . . .
C16 C 1.13896(16) 0.08993(16) 0.7951(3) 0.0894(9) Uani 1 1 d . . . . .
H16A H 1.1889 0.0528 0.8063 0.107 Uiso 1 1 calc R U . . .
H16B H 1.1620 0.1226 0.8896 0.107 Uiso 1 1 calc R U . . .
C17 C 1.12261(15) 0.12510(12) 0.6233(3) 0.0656(6) Uani 1 1 d . . . . .
H17A H 1.1756 0.1116 0.5663 0.079 Uiso 1 1 calc R U . A 1
H17B H 1.1248 0.1751 0.6380 0.079 Uiso 1 1 calc R U . A 1
C18 C 1.0150(5) 0.1020(4) 0.5126(8) 0.0449(13) Uani 0.480(7) 1 d . . P B 1
H18 H 1.0239 0.0626 0.4395 0.054 Uiso 0.480(7) 1 d R U P B 1
C19 C 0.9426(4) 0.1541(3) 0.4007(7) 0.0608(15) Uani 0.480(7) 1 d . . P B 1
H19A H 0.9403 0.1966 0.4648 0.073 Uiso 0.480(7) 1 calc R U P B 1
H19B H 0.8738 0.1351 0.3646 0.073 Uiso 0.480(7) 1 calc R U P B 1
C20 C 0.987(2) 0.1686(10) 0.236(3) 0.060(3) Uani 0.480(7) 1 d . . P B 1
F1 F 0.9949(8) 0.1296(5) 0.1497(10) 0.202(4) Uani 0.480(7) 1 d . . P B 1
F2 F 0.9116(4) 0.2206(4) 0.1489(11) 0.136(3) Uani 0.480(7) 1 d . . P B 1
F3 F 1.0665(11) 0.2177(7) 0.3113(16) 0.155(5) Uani 0.480(7) 1 d . . P B 1
C18' C 1.0124(4) 0.1304(3) 0.5491(8) 0.0443(12) Uani 0.520(7) 1 d . . P B 2
H18' H 0.9899 0.1767 0.5755 0.053 Uiso 0.520(7) 1 d R U P B 2
C19' C 0.9723(4) 0.1174(3) 0.3558(5) 0.0551(13) Uani 0.520(7) 1 d . . P B 2
H19C H 0.9006 0.1041 0.3295 0.066 Uiso 0.520(7) 1 calc R U P B 2
H19D H 1.0109 0.0803 0.3188 0.066 Uiso 0.520(7) 1 calc R U P B 2
C20' C 0.985(2) 0.1863(9) 0.260(3) 0.070(4) Uani 0.520(7) 1 d . . P B 2
F1' F 0.9633(4) 0.1633(4) 0.0811(5) 0.1100(19) Uani 0.520(7) 1 d . . P B 2
F2' F 0.9418(6) 0.2340(3) 0.2720(9) 0.129(2) Uani 0.520(7) 1 d . . P B 2
F3' F 1.0837(8) 0.1933(6) 0.2690(13) 0.110(3) Uani 0.520(7) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.225(2) . ?
N1 N2 1.238(2) . ?
N1 C2 1.506(2) . ?
N2 N3 1.126(2) . ?
N4 C15 1.318(2) . ?
N4 C1 1.357(2) . ?
N5 C15 1.304(2) . ?
N5 C16 1.455(2) . ?
N5 H5N 0.8495 . ?
C1 C2 1.555(2) . ?
C2 C8 1.529(2) . ?
C2 C14 1.529(2) . ?
C3 C8 1.379(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.362(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9300 . ?
C9 C10 1.381(3) . ?
C9 C14 1.387(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.360(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C15 C18 1.513(6) . ?
C15 C18' 1.556(6) . ?
C16 C17 1.491(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18' 1.457(6) . ?
C17 C18 1.561(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.521(9) . ?
C18 H18 0.9800 . ?
C19 C20 1.59(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 F1 1.041(19) . ?
C20 F3 1.44(2) . ?
C20 F2 1.47(3) . ?
C18' C19' 1.517(8) . ?
C18' H18' 0.9801 . ?
C19' C20' 1.56(2) . ?
C19' H19C 0.9700 . ?
C19' H19D 0.9700 . ?
C20' F2' 1.11(2) . ?
C20' F3' 1.32(3) . ?
C20' F1' 1.45(2) . ?

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
N2 N1 C2 115.46(15) . . ?
N3 N2 N1 172.4(2) . . ?
C15 N4 C1 118.65(14) . . ?
C15 N5 C16 115.11(16) . . ?
C15 N5 H5N 125.5 . . ?
C16 N5 H5N 119.3 . . ?
O1 C1 N4 127.29(15) . . ?
O1 C1 C2 119.45(14) . . ?
N4 C1 C2 113.21(14) . . ?
N1 C2 C8 104.59(13) . . ?
N1 C2 C14 111.20(13) . . ?
C8 C2 C14 112.90(13) . . ?
N1 C2 C1 108.68(13) . . ?
C8 C2 C1 110.14(13) . . ?
C14 C2 C1 109.20(13) . . ?
C8 C3 C4 121.0(2) . . ?
C8 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C3 C8 C7 118.09(18) . . ?
C3 C8 C2 119.94(16) . . ?
C7 C8 C2 121.94(17) . . ?
C10 C9 C14 120.69(19) . . ?
C10 C9 H9 119.7 . . ?
C14 C9 H9 119.7 . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C9 117.85(17) . . ?
C13 C14 C2 121.87(16) . . ?
C9 C14 C2 120.25(16) . . ?
N5 C15 N4 130.41(16) . . ?
N5 C15 C18 109.7(3) . . ?
N4 C15 C18 118.9(3) . . ?
N5 C15 C18' 106.4(3) . . ?
N4 C15 C18' 122.0(2) . . ?
N5 C16 C17 103.39(16) . . ?
N5 C16 H16A 111.1 . . ?
C17 C16 H16A 111.1 . . ?
N5 C16 H16B 111.1 . . ?
C17 C16 H16B 111.1 . . ?
H16A C16 H16B 109.0 . . ?
C18' C17 C16 107.8(3) . . ?
C16 C17 C18 107.0(3) . . ?
C16 C17 H17A 110.3 . . ?
C18 C17 H17A 110.3 . . ?
C16 C17 H17B 110.3 . . ?
C18 C17 H17B 110.3 . . ?
H17A C17 H17B 108.6 . . ?
C15 C18 C19 108.7(5) . . ?
C15 C18 C17 100.8(4) . . ?
C19 C18 C17 120.7(5) . . ?
C15 C18 H18 108.7 . . ?
C19 C18 H18 108.6 . . ?
C17 C18 H18 108.7 . . ?
C18 C19 C20 106.1(10) . . ?
C18 C19 H19A 110.5 . . ?
C20 C19 H19A 110.5 . . ?
C18 C19 H19B 110.5 . . ?
C20 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
F1 C20 F3 124(2) . . ?
F1 C20 F2 110.4(19) . . ?
F3 C20 F2 95.9(14) . . ?
F1 C20 C19 122.2(19) . . ?
F3 C20 C19 99.6(14) . . ?
F2 C20 C19 98.5(15) . . ?
C17 C18' C19' 117.9(5) . . ?
C17 C18' C15 103.6(4) . . ?
C19' C18' C15 109.8(4) . . ?
C17 C18' H18' 108.4 . . ?
C19' C18' H18' 108.4 . . ?
C15 C18' H18' 108.3 . . ?
C18' C19' C20' 107.3(9) . . ?
C18' C19' H19C 110.2 . . ?
C20' C19' H19C 110.2 . . ?
C18' C19' H19D 110.2 . . ?
C20' C19' H19D 110.2 . . ?
H19C C19' H19D 108.5 . . ?
F2' C20' F3' 117.2(17) . . ?
F2' C20' F1' 110.7(18) . . ?
F3' C20' F1' 92.4(16) . . ?
F2' C20' C19' 123(2) . . ?
F3' C20' C19' 107.1(16) . . ?
F1' C20' C19' 101.4(11) . . ?

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
C15 N4 C1 O1 -6.9(3) . . . . ?
C15 N4 C1 C2 170.70(15) . . . . ?
N2 N1 C2 C8 166.44(15) . . . . ?
N2 N1 C2 C14 44.3(2) . . . . ?
N2 N1 C2 C1 -75.94(19) . . . . ?
O1 C1 C2 N1 -137.60(17) . . . . ?
N4 C1 C2 N1 44.6(2) . . . . ?
O1 C1 C2 C8 -23.6(2) . . . . ?
N4 C1 C2 C8 158.64(15) . . . . ?
O1 C1 C2 C14 100.94(19) . . . . ?
N4 C1 C2 C14 -76.85(17) . . . . ?
C8 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C4 C3 C8 C7 0.6(3) . . . . ?
C4 C3 C8 C2 178.68(19) . . . . ?
C6 C7 C8 C3 -0.4(3) . . . . ?
C6 C7 C8 C2 -178.42(17) . . . . ?
N1 C2 C8 C3 45.9(2) . . . . ?
C14 C2 C8 C3 166.94(16) . . . . ?
C1 C2 C8 C3 -70.7(2) . . . . ?
N1 C2 C8 C7 -136.11(17) . . . . ?
C14 C2 C8 C7 -15.1(2) . . . . ?
C1 C2 C8 C7 107.28(18) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C9 -0.6(3) . . . . ?
C12 C13 C14 C2 -178.3(2) . . . . ?
C10 C9 C14 C13 0.8(3) . . . . ?
C10 C9 C14 C2 178.59(18) . . . . ?
N1 C2 C14 C13 -141.47(18) . . . . ?
C8 C2 C14 C13 101.3(2) . . . . ?
C1 C2 C14 C13 -21.5(2) . . . . ?
N1 C2 C14 C9 40.8(2) . . . . ?
C8 C2 C14 C9 -76.4(2) . . . . ?
C1 C2 C14 C9 160.75(16) . . . . ?
C16 N5 C15 N4 -178.4(2) . . . . ?
C16 N5 C15 C18 13.4(4) . . . . ?
C16 N5 C15 C18' -11.1(3) . . . . ?
C1 N4 C15 N5 2.3(3) . . . . ?
C1 N4 C15 C18 169.6(3) . . . . ?
C1 N4 C15 C18' -163.3(3) . . . . ?
C15 N5 C16 C17 -0.4(3) . . . . ?
N5 C16 C17 C18' 12.5(4) . . . . ?
N5 C16 C17 C18 -12.2(4) . . . . ?
N5 C15 C18 C19 -147.3(5) . . . . ?
N4 C15 C18 C19 42.9(7) . . . . ?
N5 C15 C18 C17 -19.4(5) . . . . ?
N4 C15 C18 C17 170.8(2) . . . . ?
C16 C17 C18 C15 18.7(5) . . . . ?
C16 C17 C18 C19 138.2(5) . . . . ?
C15 C18 C19 C20 -169.7(8) . . . . ?
C17 C18 C19 C20 74.8(10) . . . . ?
C18 C19 C20 F1 61(2) . . . . ?
C18 C19 C20 F3 -80.5(14) . . . . ?
C18 C19 C20 F2 -178.1(9) . . . . ?
C16 C17 C18' C19' -139.9(5) . . . . ?
C16 C17 C18' C15 -18.3(4) . . . . ?
N5 C15 C18' C17 18.1(4) . . . . ?
N4 C15 C18' C17 -173.3(2) . . . . ?
N5 C15 C18' C19' 144.9(4) . . . . ?
N4 C15 C18' C19' -46.4(6) . . . . ?
C17 C18' C19' C20' -82.6(12) . . . . ?
C15 C18' C19' C20' 159.1(11) . . . . ?
C18' C19' C20' F2' -66(2) . . . . ?
C18' C19' C20' F3' 73.5(15) . . . . ?
C18' C19' C20' F1' 169.7(11) . . . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.036



####################################################################### 
# 
# 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_Y_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2341707'
_audit_update_record             
;
2024-03-20 deposited with the CCDC.	2024-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 F3 N3 O'
_chemical_formula_weight         373.37

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3452(5)
_cell_length_b                   16.1586(8)
_cell_length_c                   26.0208(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3508.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.02

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62306
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.1087
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.521
_diffrn_reflns_theta_max         25.095
_diffrn_reflns_theta_full        25.095
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3086
_reflns_number_gt                2268
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1383P)²+12.2219P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0027(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3086
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.0978
_refine_ls_wR_factor_ref         0.2955
_refine_ls_wR_factor_gt          0.2472
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.3108(4) 0.5456(2) -0.00793(12) 0.0428(9) Uani 1 1 d . . . . .
F1 F -0.2613(4) 0.6586(2) 0.18484(13) 0.0637(10) Uani 1 1 d . . . . .
F2 F -0.1770(7) 0.6062(3) 0.25363(17) 0.1000(16) Uani 1 1 d . . . . .
F3 F -0.0568(5) 0.7088(3) 0.22195(18) 0.0883(13) Uani 1 1 d . . . . .
N1 N 0.1454(5) 0.5346(2) 0.06186(14) 0.0376(9) Uani 1 1 d . . . . .
N2 N 0.2381(5) 0.4821(3) 0.14129(14) 0.0402(10) Uani 1 1 d . . . . .
N3 N 0.3919(5) 0.4736(2) 0.06312(14) 0.0345(9) Uani 1 1 d . . . . .
H3N H 0.4891 0.4700 0.0524 0.041 Uiso 1 1 calc R U . . .
C1 C -0.1294(8) 0.6386(4) 0.2102(2) 0.0620(17) Uani 1 1 d . . . . .
C2 C -0.0398(9) 0.5673(5) 0.1838(3) 0.0723(19) Uani 1 1 d . . . . .
H2A H 0.0501 0.5515 0.2053 0.087 Uiso 1 1 calc R U . . .
H2B H -0.1111 0.5201 0.1817 0.087 Uiso 1 1 calc R U . . .
C3 C 0.0173(9) 0.5848(5) 0.1349(2) 0.084(3) Uani 1 1 d . . . . .
H3 H 0.0728 0.6378 0.1389 0.101 Uiso 1 1 calc R U . . .
C4 C -0.0896(8) 0.5974(5) 0.0875(2) 0.0668(18) Uani 1 1 d . . . . .
H4A H -0.1695 0.5540 0.0850 0.080 Uiso 1 1 calc R U . . .
H4B H -0.1434 0.6506 0.0889 0.080 Uiso 1 1 calc R U . . .
C5 C 0.0253(6) 0.5938(3) 0.04313(19) 0.0436(12) Uani 1 1 d . . . . .
H5A H -0.0268 0.5739 0.0122 0.052 Uiso 1 1 calc R U . . .
H5B H 0.0727 0.6476 0.0364 0.052 Uiso 1 1 calc R U . . .
C6 C 0.1443(6) 0.5273(3) 0.11528(18) 0.0449(12) Uani 1 1 d . . . . .
C7 C 0.2871(5) 0.5186(3) 0.03568(17) 0.0361(10) Uani 1 1 d . . . . .
C8 C 0.3475(5) 0.4304(3) 0.11049(16) 0.0342(10) Uani 1 1 d . . . . .
C9 C 0.50140(18) 0.41149(9) 0.14031(7) 0.0319(10) Uani 1 1 d G . . . .
C10 C 0.5207(2) 0.43578(12) 0.19118(7) 0.0344(10) Uani 1 1 d G . . . .
H10 H 0.4406 0.4660 0.2075 0.041 Uiso 1 1 calc R U . . .
C11 C 0.6597(2) 0.41497(15) 0.21764(7) 0.0370(10) Uani 1 1 d G . . . .
H11 H 0.6726 0.4312 0.2517 0.044 Uiso 1 1 calc R U . . .
C12 C 0.7793(2) 0.36987(14) 0.19323(9) 0.0389(11) Uani 1 1 d G . . . .
H12 H 0.8723 0.3560 0.2109 0.047 Uiso 1 1 calc R U . . .
C13 C 0.76006(16) 0.34558(14) 0.14236(9) 0.0381(11) Uani 1 1 d G . . . .
H13 H 0.8401 0.3154 0.1260 0.046 Uiso 1 1 calc R U . . .
C14 C 0.62109(17) 0.36639(12) 0.11590(7) 0.0378(11) Uani 1 1 d G . . . .
H14 H 0.6082 0.3501 0.0819 0.045 Uiso 1 1 calc R U . . .
C15 C 0.25871(18) 0.34845(10) 0.09947(7) 0.0338(10) Uani 1 1 d G . . . .
C16 C 0.19985(17) 0.30203(13) 0.14094(7) 0.0420(11) Uani 1 1 d G . . . .
H16 H 0.2169 0.3208 0.1743 0.050 Uiso 1 1 calc R U . . .
C17 C 0.1184(2) 0.23015(14) 0.13340(9) 0.0479(13) Uani 1 1 d G . . . .
H17 H 0.0813 0.2004 0.1616 0.057 Uiso 1 1 calc R U . . .
C18 C 0.0892(2) 0.19987(13) 0.08286(11) 0.0530(14) Uani 1 1 d G . . . .
H18 H 0.0321 0.1511 0.0777 0.064 Uiso 1 1 calc R U . . .
C19 C 0.1481(2) 0.24512(15) 0.04112(9) 0.0522(14) Uani 1 1 d G . . . .
H19 H 0.1308 0.2263 0.0078 0.063 Uiso 1 1 calc R U . . .
C20 C 0.2342(2) 0.31952(14) 0.04949(7) 0.0432(12) Uani 1 1 d G . . . .
H20 H 0.2745 0.3491 0.0217 0.052 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
O1 C7 1.231(6) . ?
F1 C1 1.324(7) . ?
F2 C1 1.307(7) . ?
F3 C1 1.322(8) . ?
N1 C7 1.389(6) . ?
N1 C6 1.395(6) . ?
N1 C5 1.469(6) . ?
N2 C6 1.266(6) . ?
N2 C8 1.474(6) . ?
N3 C7 1.343(6) . ?
N3 C8 1.464(6) . ?
N3 H3N 0.8600 . ?
C1 C2 1.535(9) . ?
C2 C3 1.388(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C6 1.499(7) . ?
C3 C4 1.535(7) . ?
C3 H3 0.9800 . ?
C4 C5 1.503(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C8 C9 1.532(4) . ?
C8 C15 1.545(5) . ?
C9 C10 1.3900 . ?
C9 C14 1.3900 . ?
C10 C11 1.3900 . ?
C10 H10 0.9300 . ?
C11 C12 1.3900 . ?
C11 H11 0.9300 . ?
C12 C13 1.3900 . ?
C12 H12 0.9300 . ?
C13 C14 1.3900 . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.3970 . ?
C15 C16 1.4028 . ?
C16 C17 1.3600 . ?
C16 H16 0.9300 . ?
C17 C18 1.4244 . ?
C17 H17 0.9300 . ?
C18 C19 1.3987 . ?
C18 H18 0.9300 . ?
C19 C20 1.4175 . ?
C19 H19 0.9300 . ?
C20 H20 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
C7 N1 C6 118.6(4) . . ?
C7 N1 C5 122.6(4) . . ?
C6 N1 C5 112.4(4) . . ?
C6 N2 C8 114.7(4) . . ?
C7 N3 C8 122.7(4) . . ?
C7 N3 H3N 118.6 . . ?
C8 N3 H3N 118.6 . . ?
F2 C1 F3 106.5(5) . . ?
F2 C1 F1 106.0(5) . . ?
F3 C1 F1 106.7(5) . . ?
F2 C1 C2 103.6(5) . . ?
F3 C1 C2 121.6(6) . . ?
F1 C1 C2 111.4(6) . . ?
C3 C2 C1 115.2(6) . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C2 C3 C6 115.4(6) . . ?
C2 C3 C4 124.3(7) . . ?
C6 C3 C4 102.7(4) . . ?
C2 C3 H3 104.1 . . ?
C6 C3 H3 104.1 . . ?
C4 C3 H3 104.1 . . ?
C5 C4 C3 104.0(5) . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
N1 C5 C4 101.9(4) . . ?
N1 C5 H5A 111.4 . . ?
C4 C5 H5A 111.4 . . ?
N1 C5 H5B 111.4 . . ?
C4 C5 H5B 111.4 . . ?
H5A C5 H5B 109.3 . . ?
N2 C6 N1 125.3(4) . . ?
N2 C6 C3 127.8(5) . . ?
N1 C6 C3 106.9(4) . . ?
O1 C7 N3 125.2(4) . . ?
O1 C7 N1 121.5(4) . . ?
N3 C7 N1 113.2(4) . . ?
N3 C8 N2 110.2(3) . . ?
N3 C8 C9 108.0(3) . . ?
N2 C8 C9 110.9(3) . . ?
N3 C8 C15 111.9(3) . . ?
N2 C8 C15 106.8(3) . . ?
C9 C8 C15 108.9(3) . . ?
C10 C9 C14 120.0 . . ?
C10 C9 C8 121.54(18) . . ?
C14 C9 C8 118.43(18) . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 120.0 . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C20 C15 C16 119.1 . . ?
C20 C15 C8 121.99(18) . . ?
C16 C15 C8 118.93(18) . . ?
C17 C16 C15 121.4 . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 120.8 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 118.5 . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C18 C19 C20 120.2 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.1 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?

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
F2 C1 C2 C3 176.9(7) . . . . ?
F3 C1 C2 C3 -63.6(9) . . . . ?
F1 C1 C2 C3 63.4(9) . . . . ?
C1 C2 C3 C6 162.4(6) . . . . ?
C1 C2 C3 C4 -69.3(10) . . . . ?
C2 C3 C4 C5 -166.8(7) . . . . ?
C6 C3 C4 C5 -33.4(8) . . . . ?
C7 N1 C5 C4 -172.3(5) . . . . ?
C6 N1 C5 C4 -20.9(6) . . . . ?
C3 C4 C5 N1 32.7(6) . . . . ?
C8 N2 C6 N1 -4.1(8) . . . . ?
C8 N2 C6 C3 178.4(6) . . . . ?
C7 N1 C6 N2 -25.5(8) . . . . ?
C5 N1 C6 N2 -178.2(5) . . . . ?
C7 N1 C6 C3 152.5(5) . . . . ?
C5 N1 C6 C3 -0.3(7) . . . . ?
C2 C3 C6 N2 -22.8(11) . . . . ?
C4 C3 C6 N2 -161.2(6) . . . . ?
C2 C3 C6 N1 159.3(6) . . . . ?
C4 C3 C6 N1 20.9(8) . . . . ?
C8 N3 C7 O1 -168.4(4) . . . . ?
C8 N3 C7 N1 13.0(6) . . . . ?
C6 N1 C7 O1 -159.0(4) . . . . ?
C5 N1 C7 O1 -9.2(7) . . . . ?
C6 N1 C7 N3 19.7(6) . . . . ?
C5 N1 C7 N3 169.5(4) . . . . ?
C7 N3 C8 N2 -39.7(6) . . . . ?
C7 N3 C8 C9 -161.0(4) . . . . ?
C7 N3 C8 C15 79.1(5) . . . . ?
C6 N2 C8 N3 33.2(6) . . . . ?
C6 N2 C8 C9 152.8(4) . . . . ?
C6 N2 C8 C15 -88.6(5) . . . . ?
N3 C8 C9 C10 126.0(2) . . . . ?
N2 C8 C9 C10 5.1(4) . . . . ?
C15 C8 C9 C10 -112.2(2) . . . . ?
N3 C8 C9 C14 -56.3(3) . . . . ?
N2 C8 C9 C14 -177.2(3) . . . . ?
C15 C8 C9 C14 65.5(3) . . . . ?
C14 C9 C10 C11 0.0 . . . . ?
C8 C9 C10 C11 177.7(2) . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C9 0.0 . . . . ?
C10 C9 C14 C13 0.0 . . . . ?
C8 C9 C14 C13 -177.8(2) . . . . ?
N3 C8 C15 C20 3.1(4) . . . . ?
N2 C8 C15 C20 123.8(2) . . . . ?
C9 C8 C15 C20 -116.3(2) . . . . ?
N3 C8 C15 C16 -176.4(2) . . . . ?
N2 C8 C15 C16 -55.7(3) . . . . ?
C9 C8 C15 C16 64.2(3) . . . . ?
C20 C15 C16 C17 -0.7 . . . . ?
C8 C15 C16 C17 178.83(19) . . . . ?
C15 C16 C17 C18 -0.4 . . . . ?
C16 C17 C18 C19 0.9 . . . . ?
C17 C18 C19 C20 -0.3 . . . . ?
C16 C15 C20 C19 1.3 . . . . ?
C8 C15 C20 C19 -178.19(19) . . . . ?
C18 C19 C20 C15 -0.8 . . . . ?

_refine_diff_density_max         1.732
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.087



####################################################################### 
# 
# 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_YY
_database_code_depnum_ccdc_archive 'CCDC 2341708'
_audit_update_record             
;
2024-03-20 deposited with the CCDC.	2024-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 N6 O'
_chemical_formula_weight         400.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   12.6779(12)
_cell_length_b                   15.4791(12)
_cell_length_c                   21.483(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.233(5)
_cell_angle_gamma                90
_cell_volume                     4190.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9878
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      27.46

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            89621
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.632
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4839
_reflns_number_gt                3638
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0720P)²+3.6814P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4839
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1658
_refine_ls_wR_factor_gt          0.1525
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.54426(6) 0.33152(5) 0.55018(4) 0.0421(4) Uani 1 1 d G . . . .
C2 C 0.59049(7) 0.39778(5) 0.51890(4) 0.0525(5) Uani 1 1 d G . . . .
H2 H 0.6015 0.3911 0.4771 0.063 Uiso 1 1 calc R U . . .
C3 C 0.62020(10) 0.47408(6) 0.55014(6) 0.0686(7) Uani 1 1 d G . . . .
H3 H 0.6511 0.5184 0.5292 0.082 Uiso 1 1 calc R U . . .
C4 C 0.60370(10) 0.48412(7) 0.61264(6) 0.0770(8) Uani 1 1 d G . . . .
H4 H 0.6236 0.5352 0.6335 0.092 Uiso 1 1 calc R U . . .
C5 C 0.55747(9) 0.41787(8) 0.64392(4) 0.0772(8) Uani 1 1 d G . . . .
H5 H 0.5464 0.4246 0.6857 0.093 Uiso 1 1 calc R U . . .
C6 C 0.52775(9) 0.34157(7) 0.61268(4) 0.0610(6) Uani 1 1 d G . . . .
H6 H 0.4968 0.2972 0.6336 0.073 Uiso 1 1 calc R U . . .
C7 C 0.54462(6) 0.23993(5) 0.45143(4) 0.0408(4) Uani 1 1 d G . . . .
C8 C 0.64174(7) 0.20731(6) 0.43881(4) 0.0496(5) Uani 1 1 d G . . . .
H8 H 0.6883 0.1852 0.4713 0.060 Uiso 1 1 calc R U . . .
C9 C 0.67035(8) 0.20724(8) 0.37850(5) 0.0619(6) Uani 1 1 d G . . . .
H9 H 0.7368 0.1868 0.3710 0.074 Uiso 1 1 calc R U . . .
C10 C 0.60087(10) 0.23726(8) 0.32950(4) 0.0709(7) Uani 1 1 d G . . . .
H10 H 0.6194 0.2350 0.2888 0.085 Uiso 1 1 calc R U . . .
C11 C 0.50408(10) 0.27057(8) 0.34077(4) 0.0751(8) Uani 1 1 d G . . . .
H11 H 0.4580 0.2923 0.3079 0.090 Uiso 1 1 calc R U . . .
C12 C 0.47486(7) 0.27175(7) 0.40242(4) 0.0582(6) Uani 1 1 d G . . . .
H12 H 0.4093 0.2937 0.4101 0.070 Uiso 1 1 calc R U . . .
C13 C 0.51591(12) 0.24342(11) 0.51882(9) 0.0385(4) Uani 1 1 d . . . . .
C14 C 0.35440(12) 0.16401(11) 0.54711(8) 0.0357(4) Uani 1 1 d . . . . .
C15 C 0.53214(12) 0.11857(11) 0.58120(8) 0.0346(4) Uani 1 1 d . . . . .
C16 C 0.58794(14) 0.04742(11) 0.62068(8) 0.0387(4) Uani 1 1 d . . . . .
C17 C 0.49561(17) -0.00096(16) 0.64644(12) 0.0640(6) Uani 1 1 d . . . . .
H17A H 0.5029 -0.0627 0.6404 0.077 Uiso 1 1 calc R U . . .
H17B H 0.4962 0.0101 0.6909 0.077 Uiso 1 1 calc R U . . .
C18 C 0.39382(17) 0.03049(16) 0.61201(13) 0.0665(7) Uani 1 1 d . . . . .
H18A H 0.3627 -0.0133 0.5834 0.080 Uiso 1 1 calc R U . . .
H18B H 0.3432 0.0456 0.6410 0.080 Uiso 1 1 calc R U . . .
C19 C 0.6516(2) -0.00946(15) 0.57972(10) 0.0627(6) Uani 1 1 d . . . . .
H19A H 0.6031 -0.0389 0.5488 0.075 Uiso 1 1 calc R U . . .
H19B H 0.6975 0.0269 0.5576 0.075 Uiso 1 1 calc R U . . .
C20 C 0.7192(2) -0.07652(18) 0.61815(13) 0.0794(8) Uani 1 1 d . . . . .
H20A H 0.6733 -0.1166 0.6371 0.095 Uiso 1 1 calc R U . . .
H20B H 0.7605 -0.1091 0.5908 0.095 Uiso 1 1 calc R U . . .
C21 C 0.7929(2) -0.0333(2) 0.66866(13) 0.0775(8) Uani 1 1 d . . . . .
H21A H 0.8431 0.0026 0.6495 0.093 Uiso 1 1 calc R U . . .
H21B H 0.8326 -0.0770 0.6937 0.093 Uiso 1 1 calc R U . . .
C22 C 0.73145(19) 0.02207(18) 0.71076(11) 0.0646(6) Uani 1 1 d . . . . .
H22A H 0.7805 0.0512 0.7416 0.077 Uiso 1 1 calc R U . . .
H22B H 0.6854 -0.0143 0.7328 0.077 Uiso 1 1 calc R U . . .
C23 C 0.66532(15) 0.08861(13) 0.67172(9) 0.0449(4) Uani 1 1 d . . . . .
H23 H 0.7136 0.1262 0.6515 0.054 Uiso 1 1 calc R U . . .
N1 N 0.57884(11) 0.17826(10) 0.55559(8) 0.0442(4) Uani 1 1 d . . . . .
N2 N 0.39995(11) 0.22931(10) 0.51993(8) 0.0448(4) Uani 1 1 d . . . . .
H2N H 0.3516 0.2693 0.4983 0.054 Uiso 1 1 d R U . . .
N3 N 0.42406(11) 0.10649(10) 0.57794(8) 0.0443(4) Uani 1 1 d . . . . .
N4 N 0.60143(19) 0.14331(17) 0.71007(10) 0.0770(6) Uani 1 1 d . . . . .
N5 N 0.6491(3) 0.18900(18) 0.74823(13) 0.0996(9) Uani 1 1 d . . . . .
N6 N 0.6845(5) 0.2330(3) 0.7863(2) 0.201(2) Uani 1 1 d . . . . .
O1 O 0.25787(9) 0.15461(9) 0.54566(7) 0.0512(4) 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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C13 1.546(2) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C7 C8 1.3845 . ?
C7 C12 1.3895 . ?
C7 C13 1.532(2) . ?
C8 C9 1.3829 . ?
C9 C10 1.3779 . ?
C10 C11 1.3765 . ?
C11 C12 1.4137 . ?
C13 N1 1.463(2) . ?
C13 N2 1.489(2) . ?
C14 O1 1.229(2) . ?
C14 N2 1.330(2) . ?
C14 N3 1.373(2) . ?
C15 N1 1.256(2) . ?
C15 N3 1.377(2) . ?
C15 C16 1.517(2) . ?
C16 C23 1.529(3) . ?
C16 C19 1.535(3) . ?
C16 C17 1.542(3) . ?
C17 C18 1.497(3) . ?
C18 N3 1.459(2) . ?
C19 C20 1.529(3) . ?
C20 C21 1.509(4) . ?
C21 C22 1.520(4) . ?
C22 C23 1.521(3) . ?
C23 N4 1.482(3) . ?
N4 N5 1.196(3) . ?
N5 N6 1.120(4) . ?

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
C2 C1 C6 120.0 . . ?
C2 C1 C13 122.04(7) . . ?
C6 C1 C13 117.86(7) . . ?
C1 C2 C3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C8 C7 C12 119.2 . . ?
C8 C7 C13 120.37(7) . . ?
C12 C7 C13 120.44(7) . . ?
C9 C8 C7 120.9 . . ?
C10 C9 C8 120.3 . . ?
C11 C10 C9 120.0 . . ?
C10 C11 C12 119.9 . . ?
C7 C12 C11 119.7 . . ?
N1 C13 N2 111.82(13) . . ?
N1 C13 C7 108.33(13) . . ?
N2 C13 C7 110.26(13) . . ?
N1 C13 C1 106.58(13) . . ?
N2 C13 C1 107.79(13) . . ?
C7 C13 C1 112.03(11) . . ?
O1 C14 N2 123.86(16) . . ?
O1 C14 N3 121.46(16) . . ?
N2 C14 N3 114.67(14) . . ?
N1 C15 N3 126.25(15) . . ?
N1 C15 C16 124.43(15) . . ?
N3 C15 C16 109.32(14) . . ?
C15 C16 C23 108.79(14) . . ?
C15 C16 C19 109.78(15) . . ?
C23 C16 C19 108.28(16) . . ?
C15 C16 C17 103.12(14) . . ?
C23 C16 C17 113.46(17) . . ?
C19 C16 C17 113.23(19) . . ?
C18 C17 C16 108.18(17) . . ?
N3 C18 C17 104.52(16) . . ?
C20 C19 C16 112.25(18) . . ?
C21 C20 C19 110.7(2) . . ?
C20 C21 C22 111.2(2) . . ?
C21 C22 C23 109.91(18) . . ?
N4 C23 C22 112.46(18) . . ?
N4 C23 C16 106.86(16) . . ?
C22 C23 C16 112.67(17) . . ?
C15 N1 C13 119.22(14) . . ?
C14 N2 C13 126.50(14) . . ?
C14 N3 C15 121.39(14) . . ?
C14 N3 C18 125.09(15) . . ?
C15 N3 C18 113.48(15) . . ?
N5 N4 C23 117.0(2) . . ?
N6 N5 N4 173.2(4) . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.039



