# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_yhb-2-20221012
_database_code_depnum_ccdc_archive 'CCDC 2224582'
loop_
_audit_author_name
_audit_author_address
guohonghong
;TYUT
China
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;
_audit_creation_date             2022-10-12
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 F2 N3'
_chemical_formula_sum            'C27 H19 F2 N3'
_chemical_formula_weight         423.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 F1 N1 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1865(2)
_cell_length_b                   11.3004(2)
_cell_length_c                   19.1635(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.307(2)
_cell_angle_gamma                90
_cell_volume                     2146.71(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5785
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0480
_cell_measurement_theta_min      4.5520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             880
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10518
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.497
_diffrn_reflns_theta_min         4.544
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -13.00   1.00    1.00    --  -35.62 147.00  11.00   89
  2  ω    -69.00 -44.00   1.00    1.00    --  -35.62 124.00-153.00   25
  3  ω     31.00  56.00   1.00    1.00    --   35.62-124.00 127.00   25
  4  ω    103.00 128.00   1.00    1.24    --  107.12 147.00  11.00   25
  5  ω     42.00 115.00   1.00    1.24    --  107.12-124.00 127.00   73
  6  ω    111.00 136.00   1.00    1.24    --  107.12 124.00-153.00   25
  7  ω     86.00 113.00   1.00    1.24    --  107.12-147.00 -37.00   27
  8  ω    -93.00 -40.00   1.00    1.00    --  -35.62 178.00-120.00   53
  9  ω   -102.00 -20.00   1.00    1.00    --  -35.62 -57.00 -90.00   82
 10  ω     20.00  99.00   1.00    1.00    --   35.62  57.00  30.00   79
 11  ω     24.00  72.00   1.00    1.00    --   35.62 -99.00 -60.00   48
 12  ω     81.00 106.00   1.00    1.24    --  107.12 -95.00   0.00   25
 13  ω     49.00  80.00   1.00    1.24    --  107.12 -95.00 -30.00   31
 14  ω    119.00 174.00   1.00    1.24    --  107.12  45.00-150.00   55
 15  ω     90.00 176.00   1.00    1.24    --  107.12  45.00   0.00   86
 16  ω     48.00 110.00   1.00    1.24    --  107.12 -95.00 150.00   62
 17  ω    100.00 175.00   1.00    1.24    --  107.12 111.00  30.00   75
 18  ω    102.00 167.00   1.00    1.24    --  107.12 111.00 150.00   65
 19  ω    133.00 169.00   1.00    1.24    --  107.12 111.00  60.00   36
 20  ω    103.00 128.00   1.00    1.24    --  107.12  61.00 -60.00   25
 21  ω     37.00 120.00   1.00    1.24    --  107.12 -30.00  60.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0315789000
_diffrn_orient_matrix_UB_12      -0.1329409000
_diffrn_orient_matrix_UB_13      -0.0117631000
_diffrn_orient_matrix_UB_21      -0.1040308000
_diffrn_orient_matrix_UB_22      0.0286884000
_diffrn_orient_matrix_UB_23      -0.0699740000
_diffrn_orient_matrix_UB_31      0.1109060000
_diffrn_orient_matrix_UB_32      -0.0108180000
_diffrn_orient_matrix_UB_33      -0.0423053000
_diffrn_oxdiff_digest_frames     
;
01473b9dfc98ce9f966b3a0889676fd31800030107c
;
_diffrn_oxdiff_digest_hkl        
;
01a56ec8086894cece25038b96f5cc11f59884
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3534
_reflns_number_total             4088
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0803P)²+0.4810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1584
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C8(H8), C25(H25), C12(H12), C21(H21), C23(H23), C32(H32), C18(H18),
 C28(H28), C22(H22), C16(H16), C17(H17), C11(H11), C9(H9), C10(H10), C31(H31),
 C29(H29), C30(H30)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F19 F 0.07484(13) 0.12754(12) 0.04601(8) 0.0709(4) Uani 1 1 d . . . . .
F26 F 0.79983(16) 0.40688(14) 0.46585(7) 0.0757(4) Uani 1 1 d . . . . .
N1 N 0.63667(13) 0.53561(13) 0.15531(8) 0.0348(3) Uani 1 1 d . . . . .
N3 N 0.49684(14) 0.44797(13) 0.22139(8) 0.0370(3) Uani 1 1 d . . . . .
N5 N 0.43068(14) 0.44090(12) 0.09332(8) 0.0366(3) Uani 1 1 d . . . . .
C7 C 0.76898(16) 0.53455(15) 0.14171(9) 0.0346(4) Uani 1 1 d . . . . .
C4 C 0.42144(15) 0.40570(15) 0.15582(9) 0.0336(4) Uani 1 1 d . . . . .
C2 C 0.60866(16) 0.50145(14) 0.21870(9) 0.0334(4) Uani 1 1 d . . . . .
C6 C 0.51847(16) 0.54303(14) 0.09424(9) 0.0341(4) Uani 1 1 d . . . . .
H6 H 0.551618 0.540901 0.050139 0.041 Uiso 1 1 calc R . . . .
C13 C 0.32679(16) 0.30776(15) 0.16184(10) 0.0360(4) Uani 1 1 d . . . . .
C27 C 0.43770(17) 0.65626(16) 0.09318(10) 0.0393(4) Uani 1 1 d . . . . .
C20 C 0.70540(16) 0.52821(15) 0.28748(9) 0.0355(4) Uani 1 1 d . . . . .
C14 C 0.24415(17) 0.26144(16) 0.09981(10) 0.0405(4) Uani 1 1 d . . . . .
H14 H 0.247818 0.290506 0.054902 0.049 Uiso 1 1 calc R . . . .
C8 C 0.80593(19) 0.62243(18) 0.09992(11) 0.0460(4) Uani 1 1 d . . . . .
H8 H 0.746067 0.683113 0.081842 0.055 Uiso 1 1 calc R . . . .
C25 C 0.70848(18) 0.45450(16) 0.34552(10) 0.0411(4) Uani 1 1 d . . . . .
H25 H 0.653302 0.388037 0.340892 0.049 Uiso 1 1 calc R . . . .
C12 C 0.8578(2) 0.44411(18) 0.16838(11) 0.0474(5) Uani 1 1 d . . . . .
H12 H 0.832591 0.384296 0.195978 0.057 Uiso 1 1 calc R . . . .
C15 C 0.15678(18) 0.17146(17) 0.10658(12) 0.0473(5) Uani 1 1 d . . . . .
C21 C 0.7883(2) 0.62828(17) 0.29596(11) 0.0457(4) Uani 1 1 d . . . . .
H21 H 0.787638 0.677978 0.257199 0.055 Uiso 1 1 calc R . . . .
C24 C 0.7942(2) 0.48106(18) 0.40998(10) 0.0473(5) Uani 1 1 d . . . . .
C23 C 0.8761(2) 0.57948(19) 0.42009(11) 0.0516(5) Uani 1 1 d . . . . .
H23 H 0.932650 0.595754 0.464513 0.062 Uiso 1 1 calc R . . . .
C32 C 0.3158(2) 0.6646(2) 0.04242(13) 0.0553(5) Uani 1 1 d . . . . .
H32 H 0.286737 0.602160 0.011057 0.066 Uiso 1 1 calc R . . . .
C18 C 0.3194(2) 0.26165(19) 0.22814(11) 0.0496(5) Uani 1 1 d . . . . .
H18 H 0.374609 0.291875 0.269868 0.060 Uiso 1 1 calc R . . . .
C28 C 0.4795(3) 0.75027(18) 0.13875(13) 0.0577(5) Uani 1 1 d . . . . .
H28 H 0.561352 0.745963 0.172369 0.069 Uiso 1 1 calc R . . . .
C22 C 0.8714(2) 0.6530(2) 0.36231(12) 0.0541(5) Uani 1 1 d . . . . .
H22 H 0.925022 0.720557 0.367960 0.065 Uiso 1 1 calc R . . . .
C16 C 0.1475(2) 0.12437(19) 0.17108(13) 0.0556(5) Uani 1 1 d . . . . .
H16 H 0.087515 0.063285 0.173568 0.067 Uiso 1 1 calc R . . . .
C17 C 0.2300(2) 0.1707(2) 0.23217(13) 0.0596(6) Uani 1 1 d . . . . .
H17 H 0.225693 0.140490 0.276746 0.071 Uiso 1 1 calc R . . . .
C11 C 0.9844(2) 0.4435(2) 0.15363(13) 0.0632(6) Uani 1 1 d . . . . .
H11 H 1.045075 0.383543 0.172120 0.076 Uiso 1 1 calc R . . . .
C9 C 0.9323(2) 0.6196(2) 0.08517(13) 0.0623(6) Uani 1 1 d . . . . .
H9 H 0.957339 0.678434 0.056882 0.075 Uiso 1 1 calc R . . . .
C10 C 1.0215(2) 0.5304(3) 0.11198(13) 0.0671(7) Uani 1 1 d . . . . .
H10 H 1.106525 0.528914 0.101930 0.080 Uiso 1 1 calc R . . . .
C31 C 0.2379(2) 0.7656(3) 0.03860(17) 0.0759(8) Uani 1 1 d . . . . .
H31 H 0.156943 0.771036 0.004349 0.091 Uiso 1 1 calc R . . . .
C29 C 0.4008(4) 0.8511(2) 0.13491(18) 0.0799(8) Uani 1 1 d . . . . .
H29 H 0.429723 0.914135 0.165851 0.096 Uiso 1 1 calc R . . . .
C30 C 0.2791(3) 0.8579(2) 0.08500(19) 0.0851(10) Uani 1 1 d . . . . .
H30 H 0.225262 0.924874 0.082879 0.102 Uiso 1 1 calc R . . . .


_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
F19 C15 1.358(2) . ?
F26 C24 1.351(2) . ?
N1 C7 1.430(2) . ?
N1 C2 1.366(2) . ?
N1 C6 1.476(2) . ?
N3 C4 1.397(2) . ?
N3 C2 1.301(2) . ?
N5 C4 1.286(2) . ?
N5 C6 1.458(2) . ?
C7 C8 1.381(2) . ?
C7 C12 1.382(2) . ?
C4 C13 1.490(2) . ?
C2 C20 1.484(2) . ?
C6 H6 0.9800 . ?
C6 C27 1.519(2) . ?
C13 C14 1.391(2) . ?
C13 C18 1.391(3) . ?
C27 C32 1.394(3) . ?
C27 C28 1.379(3) . ?
C20 C25 1.384(2) . ?
C20 C21 1.398(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.372(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.383(3) . ?
C15 C16 1.369(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C24 C23 1.377(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.377(3) . ?
C32 H32 0.9300 . ?
C32 C31 1.382(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.388(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.386(3) . ?
C22 H22 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.378(3) . ?
C17 H17 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.372(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(4) . ?
C10 H10 0.9300 . ?
C31 H31 0.9300 . ?
C31 C30 1.372(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.383(5) . ?
C30 H30 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 119.15(13) . . ?
C2 N1 C7 123.93(14) . . ?
C2 N1 C6 114.96(13) . . ?
C2 N3 C4 115.35(14) . . ?
C4 N5 C6 114.19(14) . . ?
C8 C7 N1 119.57(15) . . ?
C8 C7 C12 120.23(16) . . ?
C12 C7 N1 120.17(16) . . ?
N3 C4 C13 114.57(14) . . ?
N5 C4 N3 126.08(15) . . ?
N5 C4 C13 119.30(15) . . ?
N1 C2 C20 120.02(14) . . ?
N3 C2 N1 122.04(15) . . ?
N3 C2 C20 117.91(15) . . ?
N1 C6 H6 107.6 . . ?
N1 C6 C27 113.52(14) . . ?
N5 C6 N1 110.55(13) . . ?
N5 C6 H6 107.6 . . ?
N5 C6 C27 109.75(13) . . ?
C27 C6 H6 107.6 . . ?
C14 C13 C4 119.25(16) . . ?
C14 C13 C18 119.36(16) . . ?
C18 C13 C4 121.39(16) . . ?
C32 C27 C6 117.36(17) . . ?
C28 C27 C6 123.58(17) . . ?
C28 C27 C32 119.06(19) . . ?
C25 C20 C2 118.60(15) . . ?
C25 C20 C21 119.47(16) . . ?
C21 C20 C2 121.87(16) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.34(18) . . ?
C15 C14 H14 120.8 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.56(19) . . ?
C9 C8 H8 120.2 . . ?
C20 C25 H25 120.5 . . ?
C24 C25 C20 118.93(17) . . ?
C24 C25 H25 120.5 . . ?
C7 C12 H12 120.3 . . ?
C7 C12 C11 119.35(19) . . ?
C11 C12 H12 120.3 . . ?
F19 C15 C14 118.22(19) . . ?
F19 C15 C16 118.22(18) . . ?
C16 C15 C14 123.56(19) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.70(18) . . ?
C22 C21 H21 120.1 . . ?
F26 C24 C25 118.68(18) . . ?
F26 C24 C23 118.44(18) . . ?
C25 C24 C23 122.88(18) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 C24 117.84(19) . . ?
C22 C23 H23 121.1 . . ?
C27 C32 H32 119.9 . . ?
C31 C32 C27 120.1(2) . . ?
C31 C32 H32 119.9 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.6(2) . . ?
C29 C28 H28 119.7 . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.16(18) . . ?
C23 C22 H22 119.4 . . ?
C15 C16 H16 121.2 . . ?
C15 C16 C17 117.65(19) . . ?
C17 C16 H16 121.2 . . ?
C18 C17 H17 119.5 . . ?
C16 C17 C18 120.9(2) . . ?
C16 C17 H17 119.5 . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 119.72(19) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C32 C31 H31 119.8 . . ?
C30 C31 C32 120.5(3) . . ?
C30 C31 H31 119.8 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 119.9(2) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?

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
F19 C15 C16 C17 -179.25(19) . . . . ?
F26 C24 C23 C22 178.7(2) . . . . ?
N1 C7 C8 C9 -178.22(19) . . . . ?
N1 C7 C12 C11 178.88(19) . . . . ?
N1 C2 C20 C25 -152.53(16) . . . . ?
N1 C2 C20 C21 30.5(2) . . . . ?
N1 C6 C27 C32 -172.58(15) . . . . ?
N1 C6 C27 C28 8.3(2) . . . . ?
N3 C4 C13 C14 178.21(14) . . . . ?
N3 C4 C13 C18 -1.9(2) . . . . ?
N3 C2 C20 C25 29.2(2) . . . . ?
N3 C2 C20 C21 -147.77(17) . . . . ?
N5 C4 C13 C14 -4.0(2) . . . . ?
N5 C4 C13 C18 175.91(16) . . . . ?
N5 C6 C27 C32 -48.3(2) . . . . ?
N5 C6 C27 C28 132.54(18) . . . . ?
C7 N1 C2 N3 -145.19(17) . . . . ?
C7 N1 C2 C20 36.6(2) . . . . ?
C7 N1 C6 N5 121.01(15) . . . . ?
C7 N1 C6 C27 -115.16(16) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C7 C12 C11 C10 -1.1(4) . . . . ?
C4 N3 C2 N1 13.1(2) . . . . ?
C4 N3 C2 C20 -168.71(14) . . . . ?
C4 N5 C6 N1 37.38(19) . . . . ?
C4 N5 C6 C27 -88.60(17) . . . . ?
C4 C13 C14 C15 -179.60(15) . . . . ?
C4 C13 C18 C17 179.79(18) . . . . ?
C2 N1 C7 C8 -144.02(18) . . . . ?
C2 N1 C7 C12 38.0(3) . . . . ?
C2 N1 C6 N5 -43.65(19) . . . . ?
C2 N1 C6 C27 80.18(18) . . . . ?
C2 N3 C4 N5 -20.2(2) . . . . ?
C2 N3 C4 C13 157.33(14) . . . . ?
C2 C20 C25 C24 -177.70(16) . . . . ?
C2 C20 C21 C22 176.34(17) . . . . ?
C6 N1 C7 C8 52.8(2) . . . . ?
C6 N1 C7 C12 -125.22(18) . . . . ?
C6 N1 C2 N3 18.6(2) . . . . ?
C6 N1 C2 C20 -159.56(14) . . . . ?
C6 N5 C4 N3 -7.1(2) . . . . ?
C6 N5 C4 C13 175.45(13) . . . . ?
C6 C27 C32 C31 -179.78(18) . . . . ?
C6 C27 C28 C29 -180.0(2) . . . . ?
C13 C14 C15 F19 179.07(16) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C13 C18 C17 C16 0.1(3) . . . . ?
C27 C32 C31 C30 -0.6(4) . . . . ?
C27 C28 C29 C30 0.0(4) . . . . ?
C20 C25 C24 F26 -178.00(18) . . . . ?
C20 C25 C24 C23 1.3(3) . . . . ?
C20 C21 C22 C23 1.3(3) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C8 C7 C12 C11 0.9(3) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C25 C20 C21 C22 -0.6(3) . . . . ?
C25 C24 C23 C22 -0.6(3) . . . . ?
C12 C7 C8 C9 -0.2(3) . . . . ?
C12 C11 C10 C9 0.6(4) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C21 C20 C25 C24 -0.7(3) . . . . ?
C24 C23 C22 C21 -0.7(3) . . . . ?
C32 C27 C28 C29 0.9(3) . . . . ?
C32 C31 C30 C29 1.4(4) . . . . ?
C18 C13 C14 C15 0.5(3) . . . . ?
C28 C27 C32 C31 -0.6(3) . . . . ?
C28 C29 C30 C31 -1.2(4) . . . . ?

_olex2_date_sample_data_collection 2022-10-12
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.151
_oxdiff_exptl_absorpt_empirical_full_min 0.493
####################################################################### 
# 
# 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_yhb-3-20221013
_database_code_depnum_ccdc_archive 'CCDC 2224587'
loop_
_audit_author_name
_audit_author_address
guohonghong
;TYUT
China
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H42 N6'
_chemical_formula_weight         678.85

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'

_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                   9.5634(5)
_cell_length_b                   33.8247(15)
_cell_length_c                   12.5950(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.385(6)
_cell_angle_gamma                90
_cell_volume                     3793.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14633
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.393
_diffrn_reflns_theta_max         29.029
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.815
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.815
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             8234
_reflns_number_gt                5048
_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, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0786P)²+1.6752P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8234
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.2194
_refine_ls_wR_factor_gt          0.1913
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.220
_refine_ls_shift/su_mean         0.003

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
N1 N 0.4605(2) 0.39313(6) 0.52091(18) 0.0505(5) Uani 1 1 d . . . . .
N5 N 0.3573(2) 0.33039(6) 0.47158(17) 0.0493(5) Uani 1 1 d . . . . .
N29 N 0.8695(3) 0.33628(7) 0.4496(2) 0.0591(6) Uani 1 1 d . . . . .
N27 N 0.8639(2) 0.37786(7) 0.3005(2) 0.0589(6) Uani 1 1 d . . . . .
N3 N 0.3976(3) 0.36974(7) 0.3283(2) 0.0597(6) Uani 1 1 d . . . . .
C6 C 0.4059(3) 0.35898(7) 0.5467(2) 0.0457(6) Uani 1 1 d . . . . .
N31 N 0.9909(3) 0.39909(9) 0.4940(2) 0.0724(7) Uani 1 1 d . . . . .
C33 C 0.7731(3) 0.39883(8) 0.2011(2) 0.0505(6) Uani 1 1 d . . . . .
C15 C 0.4028(3) 0.35226(7) 0.6622(2) 0.0464(6) Uani 1 1 d . . . . .
C7 C 0.4743(3) 0.42995(8) 0.5799(2) 0.0504(6) Uani 1 1 d . . . . .
C4 C 0.3370(3) 0.34037(8) 0.3593(2) 0.0503(6) Uani 1 1 d . . . . .
C38 C 0.6187(3) 0.40084(8) 0.1702(2) 0.0502(6) Uani 1 1 d . . . . .
H38 H 0.572159 0.386900 0.211744 0.060 Uiso 1 1 calc R U . . .
C21 C 0.2347(3) 0.31314(8) 0.2716(2) 0.0527(6) Uani 1 1 d . . . . .
C8 C 0.3552(3) 0.44420(8) 0.6068(2) 0.0537(6) Uani 1 1 d . . . . .
H8 H 0.266580 0.429743 0.587050 0.064 Uiso 1 1 calc R U . . .
C28 C 0.8239(3) 0.34364(8) 0.3410(2) 0.0527(6) Uani 1 1 d . . . . .
C37 C 0.5336(3) 0.42344(9) 0.0779(2) 0.0584(7) Uani 1 1 d . . . . .
C2 C 0.5083(3) 0.39031(9) 0.4226(3) 0.0604(7) Uani 1 1 d . . . . .
H2A H 0.523292 0.416683 0.398402 0.072 Uiso 1 1 calc R U . . .
H2B H 0.603278 0.376351 0.445017 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6051(3) 0.45174(9) 0.6061(2) 0.0579(7) Uani 1 1 d . . . . .
H12 H 0.683697 0.442017 0.586799 0.069 Uiso 1 1 calc R U . . .
C30 C 0.9314(3) 0.36846(9) 0.5213(3) 0.0601(7) Uani 1 1 d . . . . .
C20 C 0.5185(3) 0.36553(9) 0.7599(2) 0.0576(7) Uani 1 1 d . . . . .
H20 H 0.596258 0.380538 0.752998 0.069 Uiso 1 1 calc R U . . .
C16 C 0.2879(3) 0.32989(8) 0.6744(2) 0.0551(7) Uani 1 1 d . . . . .
H16 H 0.211483 0.320199 0.610165 0.066 Uiso 1 1 calc R U . . .
C34 C 0.8432(3) 0.41923(9) 0.1389(3) 0.0619(7) Uani 1 1 d . . . . .
H34 H 0.946558 0.417048 0.158433 0.074 Uiso 1 1 calc R U . . .
C41 C 0.7308(3) 0.31407(8) 0.2593(2) 0.0562(7) Uani 1 1 d . . . . .
C11 C 0.6201(4) 0.48794(9) 0.6608(2) 0.0639(8) Uani 1 1 d . . . . .
C22 C 0.1641(3) 0.28219(9) 0.3027(3) 0.0669(8) Uani 1 1 d . . . . .
H22 H 0.174038 0.279363 0.378551 0.080 Uiso 1 1 calc R U . . .
C19 C 0.5183(4) 0.35654(10) 0.8663(2) 0.0669(8) Uani 1 1 d . . . . .
H19 H 0.596736 0.365059 0.931103 0.080 Uiso 1 1 calc R U . . .
C10 C 0.5011(4) 0.50124(9) 0.6894(3) 0.0685(8) Uani 1 1 d . . . . .
H10 H 0.510534 0.525217 0.727580 0.082 Uiso 1 1 calc R U . . .
C18 C 0.4019(4) 0.33490(10) 0.8771(3) 0.0695(8) Uani 1 1 d . . . . .
H18 H 0.401369 0.329094 0.949178 0.083 Uiso 1 1 calc R U . . .
C36 C 0.6077(4) 0.44446(9) 0.0188(3) 0.0692(8) Uani 1 1 d . . . . .
H36 H 0.551511 0.460136 -0.042600 0.083 Uiso 1 1 calc R U . . .
C9 C 0.3685(4) 0.48001(9) 0.6631(3) 0.0641(7) Uani 1 1 d . . . . .
C42 C 0.6271(4) 0.29197(9) 0.2878(3) 0.0688(8) Uani 1 1 d . . . . .
H42 H 0.617177 0.295827 0.357831 0.083 Uiso 1 1 calc R U . . .
C35 C 0.7605(4) 0.44279(9) 0.0481(3) 0.0677(8) Uani 1 1 d . . . . .
C47 C 0.9240(3) 0.36566(10) 0.6370(3) 0.0642(8) Uani 1 1 d . . . . .
C17 C 0.2870(3) 0.32196(10) 0.7818(3) 0.0672(8) Uani 1 1 d . . . . .
H17 H 0.207858 0.307759 0.789376 0.081 Uiso 1 1 calc R U . . .
C46 C 0.7483(4) 0.30754(10) 0.1561(3) 0.0706(8) Uani 1 1 d . . . . .
H46 H 0.817674 0.322145 0.136516 0.085 Uiso 1 1 calc R U . . .
C26 C 0.2164(4) 0.31708(11) 0.1581(3) 0.0753(9) Uani 1 1 d . . . . .
H26 H 0.261050 0.338086 0.134740 0.090 Uiso 1 1 calc R U . . .
C48 C 0.8581(4) 0.33441(11) 0.6697(3) 0.0727(9) Uani 1 1 d . . . . .
H48 H 0.812475 0.314557 0.617414 0.087 Uiso 1 1 calc R U . . .
C32 C 0.9994(3) 0.39650(11) 0.3818(3) 0.0754(9) Uani 1 1 d . . . . .
H32A H 1.086970 0.381143 0.386091 0.090 Uiso 1 1 calc R U . . .
H32B H 1.010520 0.422813 0.355281 0.090 Uiso 1 1 calc R U . . .
C44 C 0.5566(5) 0.25804(11) 0.1096(4) 0.0919(12) Uani 1 1 d . . . . .
H44 H 0.496943 0.239457 0.058679 0.110 Uiso 1 1 calc R U . . .
C45 C 0.6605(5) 0.27881(11) 0.0821(3) 0.0871(11) Uani 1 1 d . . . . .
H45 H 0.673190 0.273820 0.013549 0.105 Uiso 1 1 calc R U . . .
C24 C 0.0628(4) 0.25877(12) 0.1103(3) 0.0836(10) Uani 1 1 d . . . . .
H24 H 0.006451 0.240437 0.056745 0.100 Uiso 1 1 calc R U . . .
C40 C 0.3652(4) 0.42484(12) 0.0417(3) 0.0865(11) Uani 1 1 d . . . . .
H40A H 0.320883 0.406518 -0.019606 0.130 Uiso 1 1 calc R U . . .
H40B H 0.330374 0.451074 0.016630 0.130 Uiso 1 1 calc R U . . .
H40C H 0.337072 0.417817 0.105045 0.130 Uiso 1 1 calc R U . . .
C25 C 0.1310(4) 0.28955(13) 0.0786(3) 0.0870(11) Uani 1 1 d . . . . .
H25 H 0.120294 0.292215 0.002580 0.104 Uiso 1 1 calc R U . . .
C23 C 0.0790(4) 0.25536(11) 0.2229(3) 0.0829(10) Uani 1 1 d . . . . .
H23 H 0.031942 0.234706 0.245542 0.100 Uiso 1 1 calc R U . . .
C43 C 0.5389(4) 0.26432(10) 0.2124(4) 0.0879(11) Uani 1 1 d . . . . .
H43 H 0.467794 0.249971 0.230670 0.106 Uiso 1 1 calc R U . . .
C14 C 0.7625(4) 0.51182(11) 0.6880(3) 0.0896(11) Uani 1 1 d . . . . .
H14A H 0.845376 0.497371 0.740446 0.134 Uiso 1 1 calc R U . . .
H14B H 0.751830 0.536541 0.721757 0.134 Uiso 1 1 calc R U . . .
H14C H 0.780741 0.516732 0.619108 0.134 Uiso 1 1 calc R U . . .
C50 C 0.9243(5) 0.36147(18) 0.8565(3) 0.1035(15) Uani 1 1 d . . . . .
H50 H 0.923999 0.360192 0.930164 0.124 Uiso 1 1 calc R U . . .
C51 C 0.9898(5) 0.39252(17) 0.8248(4) 0.1041(15) Uani 1 1 d . . . . .
H51 H 1.034620 0.412297 0.877596 0.125 Uiso 1 1 calc R U . . .
C49 C 0.8586(4) 0.33195(14) 0.7800(3) 0.0912(11) Uani 1 1 d . . . . .
H49 H 0.814665 0.310442 0.801797 0.109 Uiso 1 1 calc R U . . .
C52 C 0.9913(4) 0.39542(13) 0.7160(3) 0.0858(11) Uani 1 1 d . . . . .
H52 H 1.036659 0.416916 0.695534 0.103 Uiso 1 1 calc R U . . .
C13 C 0.2388(5) 0.49600(12) 0.6919(4) 0.1057(14) Uani 1 1 d . . . . .
H13A H 0.145691 0.488357 0.633699 0.159 Uiso 1 1 calc R U . . .
H13B H 0.244928 0.524316 0.696441 0.159 Uiso 1 1 calc R U . . .
H13C H 0.243625 0.485468 0.763953 0.159 Uiso 1 1 calc R U . . .
C39 C 0.8385(5) 0.46585(13) -0.0174(4) 0.1059(14) Uani 1 1 d . . . . .
H39A H 0.842952 0.493285 0.003069 0.159 Uiso 1 1 calc R U . . .
H39B H 0.783481 0.463024 -0.097774 0.159 Uiso 1 1 calc R U . . .
H39C H 0.938531 0.455856 0.000870 0.159 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
N1 C6 1.355(3) . ?
N1 C7 1.432(3) . ?
N1 C2 1.471(3) . ?
N5 C6 1.313(3) . ?
N5 C4 1.397(3) . ?
N29 C28 1.299(4) . ?
N29 C30 1.401(4) . ?
N27 C28 1.374(3) . ?
N27 C33 1.425(3) . ?
N27 C32 1.469(4) . ?
N3 C4 1.280(3) . ?
N3 C2 1.449(4) . ?
C6 C15 1.484(3) . ?
N31 C30 1.287(4) . ?
N31 C32 1.447(4) . ?
C33 C38 1.384(4) . ?
C33 C34 1.387(4) . ?
C15 C16 1.388(4) . ?
C15 C20 1.396(4) . ?
C7 C12 1.385(4) . ?
C7 C8 1.388(4) . ?
C4 C21 1.496(4) . ?
C38 C37 1.381(4) . ?
C38 H38 0.9300 . ?
C21 C22 1.378(4) . ?
C21 C26 1.382(4) . ?
C8 C9 1.386(4) . ?
C8 H8 0.9300 . ?
C28 C41 1.477(4) . ?
C37 C36 1.395(4) . ?
C37 C40 1.505(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C12 C11 1.387(4) . ?
C12 H12 0.9300 . ?
C30 C47 1.487(4) . ?
C20 C19 1.375(4) . ?
C20 H20 0.9300 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9300 . ?
C34 C35 1.382(4) . ?
C34 H34 0.9300 . ?
C41 C46 1.386(4) . ?
C41 C42 1.390(4) . ?
C11 C10 1.388(4) . ?
C11 C14 1.512(4) . ?
C22 C23 1.378(4) . ?
C22 H22 0.9300 . ?
C19 C18 1.380(4) . ?
C19 H19 0.9300 . ?
C10 C9 1.389(4) . ?
C10 H10 0.9300 . ?
C18 C17 1.371(4) . ?
C18 H18 0.9300 . ?
C36 C35 1.372(5) . ?
C36 H36 0.9300 . ?
C9 C13 1.513(5) . ?
C42 C43 1.380(5) . ?
C42 H42 0.9300 . ?
C35 C39 1.515(4) . ?
C47 C48 1.368(5) . ?
C47 C52 1.397(5) . ?
C17 H17 0.9300 . ?
C46 C45 1.396(5) . ?
C46 H46 0.9300 . ?
C26 C25 1.392(5) . ?
C26 H26 0.9300 . ?
C48 C49 1.391(5) . ?
C48 H48 0.9300 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C44 C45 1.361(6) . ?
C44 C43 1.383(6) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C24 C25 1.363(5) . ?
C24 C23 1.375(5) . ?
C24 H24 0.9300 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C25 H25 0.9300 . ?
C23 H23 0.9300 . ?
C43 H43 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C50 C51 1.355(7) . ?
C50 C49 1.370(6) . ?
C50 H50 0.9300 . ?
C51 C52 1.380(6) . ?
C51 H51 0.9300 . ?
C49 H49 0.9300 . ?
C52 H52 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?

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
C6 N1 C7 126.0(2) . . ?
C6 N1 C2 114.3(2) . . ?
C7 N1 C2 119.7(2) . . ?
C6 N5 C4 115.7(2) . . ?
C28 N29 C30 115.5(3) . . ?
C28 N27 C33 125.6(2) . . ?
C28 N27 C32 113.4(2) . . ?
C33 N27 C32 119.9(2) . . ?
C4 N3 C2 113.6(2) . . ?
N5 C6 N1 121.4(2) . . ?
N5 C6 C15 117.7(2) . . ?
N1 C6 C15 120.8(2) . . ?
C30 N31 C32 113.6(3) . . ?
C38 C33 C34 120.2(3) . . ?
C38 C33 N27 121.1(2) . . ?
C34 C33 N27 118.6(2) . . ?
C16 C15 C20 118.9(2) . . ?
C16 C15 C6 119.5(2) . . ?
C20 C15 C6 121.5(2) . . ?
C12 C7 C8 120.5(3) . . ?
C12 C7 N1 119.4(2) . . ?
C8 C7 N1 120.0(2) . . ?
N3 C4 N5 125.8(2) . . ?
N3 C4 C21 120.0(2) . . ?
N5 C4 C21 114.3(2) . . ?
C37 C38 C33 120.3(3) . . ?
C37 C38 H38 119.8 . . ?
C33 C38 H38 119.8 . . ?
C22 C21 C26 118.5(3) . . ?
C22 C21 C4 120.9(2) . . ?
C26 C21 C4 120.4(3) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
N29 C28 N27 121.3(3) . . ?
N29 C28 C41 119.3(3) . . ?
N27 C28 C41 119.4(2) . . ?
C38 C37 C36 118.2(3) . . ?
C38 C37 C40 120.7(3) . . ?
C36 C37 C40 121.2(3) . . ?
N3 C2 N1 111.3(2) . . ?
N3 C2 H2A 109.4 . . ?
N1 C2 H2A 109.4 . . ?
N3 C2 H2B 109.4 . . ?
N1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C7 C12 C11 120.6(3) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
N31 C30 N29 125.2(3) . . ?
N31 C30 C47 119.8(3) . . ?
N29 C30 C47 115.0(3) . . ?
C19 C20 C15 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C35 C34 C33 120.3(3) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C46 C41 C42 119.9(3) . . ?
C46 C41 C28 120.8(3) . . ?
C42 C41 C28 119.3(3) . . ?
C12 C11 C10 118.0(3) . . ?
C12 C11 C14 120.4(3) . . ?
C10 C11 C14 121.6(3) . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C11 C10 C9 122.3(3) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C35 C36 C37 122.3(3) . . ?
C35 C36 H36 118.9 . . ?
C37 C36 H36 118.9 . . ?
C8 C9 C10 118.7(3) . . ?
C8 C9 C13 120.3(3) . . ?
C10 C9 C13 121.0(3) . . ?
C43 C42 C41 120.1(3) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C36 C35 C34 118.6(3) . . ?
C36 C35 C39 121.3(3) . . ?
C34 C35 C39 120.0(3) . . ?
C48 C47 C52 119.1(3) . . ?
C48 C47 C30 122.4(3) . . ?
C52 C47 C30 118.5(3) . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C41 C46 C45 119.2(3) . . ?
C41 C46 H46 120.4 . . ?
C45 C46 H46 120.4 . . ?
C21 C26 C25 119.9(3) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C47 C48 C49 120.8(4) . . ?
C47 C48 H48 119.6 . . ?
C49 C48 H48 119.6 . . ?
N31 C32 N27 110.9(2) . . ?
N31 C32 H32A 109.5 . . ?
N27 C32 H32A 109.5 . . ?
N31 C32 H32B 109.5 . . ?
N27 C32 H32B 109.5 . . ?
H32A C32 H32B 108.0 . . ?
C45 C44 C43 120.6(4) . . ?
C45 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C44 C45 C46 120.4(4) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C25 C24 C23 118.7(3) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.7 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C24 C25 C26 121.2(3) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C42 C43 C44 119.7(4) . . ?
C42 C43 H43 120.1 . . ?
C44 C43 H43 120.1 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C51 C50 C49 120.1(4) . . ?
C51 C50 H50 120.0 . . ?
C49 C50 H50 120.0 . . ?
C50 C51 C52 121.4(4) . . ?
C50 C51 H51 119.3 . . ?
C52 C51 H51 119.3 . . ?
C50 C49 C48 119.5(4) . . ?
C50 C49 H49 120.3 . . ?
C48 C49 H49 120.3 . . ?
C51 C52 C47 119.2(4) . . ?
C51 C52 H52 120.4 . . ?
C47 C52 H52 120.4 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C35 C39 H39A 109.5 . . ?
C35 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C35 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N5 C6 N1 -12.6(3) . . . . ?
C4 N5 C6 C15 169.0(2) . . . . ?
C7 N1 C6 N5 160.2(2) . . . . ?
C2 N1 C6 N5 -19.9(3) . . . . ?
C7 N1 C6 C15 -21.4(4) . . . . ?
C2 N1 C6 C15 158.5(2) . . . . ?
C28 N27 C33 C38 35.3(4) . . . . ?
C32 N27 C33 C38 -132.0(3) . . . . ?
C28 N27 C33 C34 -148.3(3) . . . . ?
C32 N27 C33 C34 44.4(4) . . . . ?
N5 C6 C15 C16 -34.2(3) . . . . ?
N1 C6 C15 C16 147.3(2) . . . . ?
N5 C6 C15 C20 141.1(3) . . . . ?
N1 C6 C15 C20 -37.4(4) . . . . ?
C6 N1 C7 C12 135.4(3) . . . . ?
C2 N1 C7 C12 -44.6(4) . . . . ?
C6 N1 C7 C8 -46.9(4) . . . . ?
C2 N1 C7 C8 133.2(3) . . . . ?
C2 N3 C4 N5 7.3(4) . . . . ?
C2 N3 C4 C21 -172.5(2) . . . . ?
C6 N5 C4 N3 20.3(4) . . . . ?
C6 N5 C4 C21 -159.9(2) . . . . ?
C34 C33 C38 C37 -0.6(4) . . . . ?
N27 C33 C38 C37 175.7(2) . . . . ?
N3 C4 C21 C22 -177.7(3) . . . . ?
N5 C4 C21 C22 2.5(4) . . . . ?
N3 C4 C21 C26 6.4(4) . . . . ?
N5 C4 C21 C26 -173.4(3) . . . . ?
C12 C7 C8 C9 -1.8(4) . . . . ?
N1 C7 C8 C9 -179.5(2) . . . . ?
C30 N29 C28 N27 13.7(4) . . . . ?
C30 N29 C28 C41 -168.1(2) . . . . ?
C33 N27 C28 N29 -146.7(3) . . . . ?
C32 N27 C28 N29 21.3(4) . . . . ?
C33 N27 C28 C41 35.1(4) . . . . ?
C32 N27 C28 C41 -156.8(3) . . . . ?
C33 C38 C37 C36 -1.0(4) . . . . ?
C33 C38 C37 C40 178.2(3) . . . . ?
C4 N3 C2 N1 -38.9(3) . . . . ?
C6 N1 C2 N3 45.7(3) . . . . ?
C7 N1 C2 N3 -134.3(2) . . . . ?
C8 C7 C12 C11 0.8(4) . . . . ?
N1 C7 C12 C11 178.5(2) . . . . ?
C32 N31 C30 N29 -4.4(4) . . . . ?
C32 N31 C30 C47 176.1(2) . . . . ?
C28 N29 C30 N31 -24.1(4) . . . . ?
C28 N29 C30 C47 155.4(2) . . . . ?
C16 C15 C20 C19 -0.1(4) . . . . ?
C6 C15 C20 C19 -175.4(3) . . . . ?
C20 C15 C16 C17 1.8(4) . . . . ?
C6 C15 C16 C17 177.2(3) . . . . ?
C38 C33 C34 C35 2.2(4) . . . . ?
N27 C33 C34 C35 -174.2(3) . . . . ?
N29 C28 C41 C46 -142.8(3) . . . . ?
N27 C28 C41 C46 35.4(4) . . . . ?
N29 C28 C41 C42 35.7(4) . . . . ?
N27 C28 C41 C42 -146.1(3) . . . . ?
C7 C12 C11 C10 0.7(4) . . . . ?
C7 C12 C11 C14 -179.3(3) . . . . ?
C26 C21 C22 C23 1.0(5) . . . . ?
C4 C21 C22 C23 -175.0(3) . . . . ?
C15 C20 C19 C18 -1.2(5) . . . . ?
C12 C11 C10 C9 -1.3(4) . . . . ?
C14 C11 C10 C9 178.7(3) . . . . ?
C20 C19 C18 C17 0.7(5) . . . . ?
C38 C37 C36 C35 1.1(5) . . . . ?
C40 C37 C36 C35 -178.1(3) . . . . ?
C7 C8 C9 C10 1.2(4) . . . . ?
C7 C8 C9 C13 179.5(3) . . . . ?
C11 C10 C9 C8 0.4(5) . . . . ?
C11 C10 C9 C13 -177.9(3) . . . . ?
C46 C41 C42 C43 -1.7(5) . . . . ?
C28 C41 C42 C43 179.8(3) . . . . ?
C37 C36 C35 C34 0.4(5) . . . . ?
C37 C36 C35 C39 180.0(3) . . . . ?
C33 C34 C35 C36 -2.1(5) . . . . ?
C33 C34 C35 C39 178.4(3) . . . . ?
N31 C30 C47 C48 178.0(3) . . . . ?
N29 C30 C47 C48 -1.5(4) . . . . ?
N31 C30 C47 C52 -4.2(4) . . . . ?
N29 C30 C47 C52 176.2(3) . . . . ?
C19 C18 C17 C16 1.1(5) . . . . ?
C15 C16 C17 C18 -2.3(5) . . . . ?
C42 C41 C46 C45 0.2(5) . . . . ?
C28 C41 C46 C45 178.7(3) . . . . ?
C22 C21 C26 C25 -1.5(5) . . . . ?
C4 C21 C26 C25 174.6(3) . . . . ?
C52 C47 C48 C49 -0.4(5) . . . . ?
C30 C47 C48 C49 177.3(3) . . . . ?
C30 N31 C32 N27 39.0(4) . . . . ?
C28 N27 C32 N31 -47.8(4) . . . . ?
C33 N27 C32 N31 120.9(3) . . . . ?
C43 C44 C45 C46 -1.7(6) . . . . ?
C41 C46 C45 C44 1.5(5) . . . . ?
C23 C24 C25 C26 0.4(6) . . . . ?
C21 C26 C25 C24 0.8(6) . . . . ?
C25 C24 C23 C22 -0.9(6) . . . . ?
C21 C22 C23 C24 0.2(5) . . . . ?
C41 C42 C43 C44 1.5(5) . . . . ?
C45 C44 C43 C42 0.2(6) . . . . ?
C49 C50 C51 C52 0.4(6) . . . . ?
C51 C50 C49 C48 -0.8(6) . . . . ?
C47 C48 C49 C50 0.8(5) . . . . ?
C50 C51 C52 C47 0.0(6) . . . . ?
C48 C47 C52 C51 0.0(5) . . . . ?
C30 C47 C52 C51 -177.8(3) . . . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042

