####################################################################### 
# 
# 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_nbvlf180119
_database_code_depnum_ccdc_archive 'CCDC 1903455'
loop_
_audit_author_name
_audit_author_address
'Lydia Karmazin'
;Universite de Strasbourg
France
;
_audit_update_record             
;
2019-03-19 deposited with the CCDC.	2019-06-05 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         'C13 H10 F N3'
_chemical_formula_sum            'C13 H10 F N3'
_chemical_formula_weight         227.24

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'
N N 0.0311 0.0180 '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'

_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                   10.17620(10)
_cell_length_b                   13.3486(2)
_cell_length_c                   14.3784(2)
_cell_angle_alpha                65.3340(10)
_cell_angle_beta                 71.4130(10)
_cell_angle_gamma                77.3550(10)
_cell_volume                     1673.96(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9840
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      66.46

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             708
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.786
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6540
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Cu-ImuS microfocus tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38060
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.499
_diffrn_reflns_theta_max         66.693
_diffrn_reflns_theta_full        66.693
_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             5908
_reflns_number_gt                5039
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0572P)²+0.5121P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5908
_refine_ls_number_parameters     475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
C1 C 0.70039(14) 0.72986(12) 0.05174(11) 0.0278(3) Uani 1 1 d . . . . .
C2 C 0.72431(15) 0.67614(12) -0.01782(12) 0.0322(3) Uani 1 1 d . . . . .
H2 H 0.7509 0.5986 0.0047 0.039 Uiso 1 1 calc R U . . .
C3 C 0.70937(16) 0.73540(14) -0.11949(12) 0.0368(4) Uani 1 1 d . . . . .
H3 H 0.7267 0.6985 -0.1669 0.044 Uiso 1 1 calc R U . . .
C4 C 0.66926(16) 0.84816(14) -0.15267(12) 0.0379(4) Uani 1 1 d . . . . .
H4 H 0.6593 0.8886 -0.2227 0.045 Uiso 1 1 calc R U . . .
C5 C 0.64374(16) 0.90199(13) -0.08372(12) 0.0367(4) Uani 1 1 d . . . . .
H5 H 0.6151 0.9792 -0.1062 0.044 Uiso 1 1 calc R U . . .
C6 C 0.65985(15) 0.84344(12) 0.01795(12) 0.0313(3) Uani 1 1 d . . . . .
H6 H 0.6432 0.8808 0.0648 0.038 Uiso 1 1 calc R U . . .
C7 C 0.71274(14) 0.66711(11) 0.16186(11) 0.0267(3) Uani 1 1 d . . . . .
C8 C 0.64308(15) 0.57473(12) 0.22861(11) 0.0285(3) Uani 1 1 d . . . . .
C9 C 0.64739(15) 0.51520(12) 0.33333(12) 0.0314(3) Uani 1 1 d . . . . .
H9 H 0.5951 0.4530 0.3737 0.038 Uiso 1 1 calc R U . . .
C10 C 0.79096(14) 0.63127(11) 0.31613(11) 0.0262(3) Uani 1 1 d . . . . .
C11 C 0.79262(14) 0.69601(11) 0.20972(11) 0.0258(3) Uani 1 1 d . . . . .
C12 C 0.88699(15) 0.77642(11) 0.17917(12) 0.0296(3) Uani 1 1 d . . . . .
C13 C 0.93793(17) 0.86570(13) 0.07495(13) 0.0405(4) Uani 1 1 d . . . . .
H13A H 1.0104 0.9003 0.0791 0.061 Uiso 1 1 calc R U . . .
H13B H 0.8603 0.9217 0.0569 0.061 Uiso 1 1 calc R U . . .
H13C H 0.9766 0.8339 0.0203 0.061 Uiso 1 1 calc R U . . .
C14 C 0.81424(15) 0.41517(12) 0.91237(12) 0.0292(3) Uani 1 1 d . . . . .
C15 C 0.91769(16) 0.39156(13) 0.96487(12) 0.0339(3) Uani 1 1 d . . . . .
H15 H 1.0110 0.4048 0.9252 0.041 Uiso 1 1 calc R U . . .
C16 C 0.88572(17) 0.34898(14) 1.07437(13) 0.0388(4) Uani 1 1 d . . . . .
H16 H 0.9576 0.3319 1.1092 0.047 Uiso 1 1 calc R U . . .
C17 C 0.75012(18) 0.33112(14) 1.13342(13) 0.0409(4) Uani 1 1 d . . . . .
H17 H 0.7287 0.3014 1.2086 0.049 Uiso 1 1 calc R U . . .
C18 C 0.64576(17) 0.35688(14) 1.08212(13) 0.0407(4) Uani 1 1 d . . . . .
H18 H 0.5521 0.3460 1.1223 0.049 Uiso 1 1 calc R U . . .
C19 C 0.67724(16) 0.39837(13) 0.97257(12) 0.0344(3) Uani 1 1 d . . . . .
H19 H 0.6050 0.4155 0.9381 0.041 Uiso 1 1 calc R U . . .
C20 C 0.84507(14) 0.46017(12) 0.79513(11) 0.0275(3) Uani 1 1 d . . . . .
C21 C 0.92350(15) 0.54849(12) 0.73118(12) 0.0311(3) Uani 1 1 d . . . . .
C22 C 0.93999(16) 0.60127(12) 0.62233(12) 0.0329(3) Uani 1 1 d . . . . .
H22 H 0.9946 0.6622 0.5850 0.039 Uiso 1 1 calc R U . . .
C23 C 0.81225(14) 0.48158(12) 0.62792(11) 0.0280(3) Uani 1 1 d . . . . .
C24 C 0.79150(14) 0.42214(11) 0.73740(11) 0.0263(3) Uani 1 1 d . . . . .
C25 C 0.72039(14) 0.33046(12) 0.75862(11) 0.0289(3) Uani 1 1 d . . . . .
C26 C 0.68187(17) 0.23165(13) 0.85739(13) 0.0388(4) Uani 1 1 d . . . . .
H26A H 0.6534 0.1766 0.8410 0.058 Uiso 1 1 calc R U . . .
H26B H 0.6045 0.2539 0.9086 0.058 Uiso 1 1 calc R U . . .
H26C H 0.7623 0.1994 0.8876 0.058 Uiso 1 1 calc R U . . .
C27 C 0.22200(15) 0.03164(12) 0.57175(13) 0.0334(3) Uani 1 1 d . . . . .
C28 C 0.25209(19) -0.04389(15) 0.52302(18) 0.0532(5) Uani 1 1 d . . . . .
H28 H 0.3353 -0.0421 0.4685 0.064 Uiso 1 1 calc R U . . .
C29 C 0.1611(2) -0.12193(18) 0.5536(2) 0.0685(6) Uani 1 1 d . . . . .
H29 H 0.1829 -0.1742 0.5206 0.082 Uiso 1 1 calc R U . . .
C30 C 0.0396(2) -0.12438(17) 0.63142(19) 0.0605(5) Uani 1 1 d . . . . .
H30 H -0.0227 -0.1780 0.6521 0.073 Uiso 1 1 calc R U . . .
C31 C 0.0088(2) -0.04938(18) 0.67881(18) 0.0600(5) Uani 1 1 d . . . . .
H31 H -0.0753 -0.0507 0.7324 0.072 Uiso 1 1 calc R U . . .
C32 C 0.09950(18) 0.02875(15) 0.64940(15) 0.0473(4) Uani 1 1 d . . . . .
H32 H 0.0771 0.0806 0.6829 0.057 Uiso 1 1 calc R U . . .
C33 C 0.31863(14) 0.11551(12) 0.54093(12) 0.0291(3) Uani 1 1 d . . . . .
C34 C 0.35051(16) 0.19610(13) 0.44104(12) 0.0348(3) Uani 1 1 d . . . . .
C35 C 0.43361(17) 0.28000(13) 0.41169(12) 0.0373(4) Uani 1 1 d . . . . .
H35 H 0.4483 0.3332 0.3412 0.045 Uiso 1 1 calc R U . . .
C36 C 0.46618(14) 0.21045(11) 0.57387(11) 0.0266(3) Uani 1 1 d . . . . .
C37 C 0.38266(14) 0.12322(11) 0.61125(11) 0.0264(3) Uani 1 1 d . . . . .
C38 C 0.39278(15) 0.06131(12) 0.71741(12) 0.0311(3) Uani 1 1 d . . . . .
C39 C 0.33068(19) -0.04273(14) 0.79627(14) 0.0462(4) Uani 1 1 d . . . . .
H39A H 0.3612 -0.0667 0.8611 0.069 Uiso 1 1 calc R U . . .
H39B H 0.3612 -0.1007 0.7668 0.069 Uiso 1 1 calc R U . . .
H39C H 0.2288 -0.0291 0.8127 0.069 Uiso 1 1 calc R U . . .
N1 N 0.72183(13) 0.54175(10) 0.37952(9) 0.0309(3) Uani 1 1 d . . . . .
N2 N 0.87539(13) 0.67333(10) 0.34364(10) 0.0299(3) Uani 1 1 d . . . . .
N3 N 0.93448(13) 0.76155(10) 0.26030(10) 0.0317(3) Uani 1 1 d . . . . .
N4 N 0.88339(13) 0.57091(10) 0.56801(10) 0.0319(3) Uani 1 1 d . . . . .
N5 N 0.75165(13) 0.43059(10) 0.59080(10) 0.0325(3) Uani 1 1 d . . . . .
N6 N 0.69658(13) 0.33813(10) 0.67021(10) 0.0322(3) Uani 1 1 d . . . . .
N7 N 0.49341(13) 0.28964(10) 0.47673(10) 0.0329(3) Uani 1 1 d . . . . .
N8 N 0.51761(13) 0.19834(10) 0.65431(10) 0.0311(3) Uani 1 1 d . . . . .
N9 N 0.47350(13) 0.10744(10) 0.74174(10) 0.0344(3) Uani 1 1 d . . . . .
F1 F 0.56088(9) 0.53859(7) 0.19295(7) 0.0359(2) Uani 1 1 d . . . . .
F2 F 0.98519(10) 0.59179(8) 0.77515(7) 0.0423(2) Uani 1 1 d . . . . .
F3 F 0.29479(11) 0.19870(9) 0.36544(8) 0.0514(3) Uani 1 1 d . . . . .
H2N H 0.8931(18) 0.6510(15) 0.4070(15) 0.041(5) Uiso 1 1 d . . . . .
H5N H 0.7379(19) 0.4569(15) 0.5230(16) 0.048(5) Uiso 1 1 d . . . . .
H8N H 0.575(2) 0.2420(16) 0.6544(15) 0.046(5) Uiso 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 1.393(2) . ?
C1 C6 1.394(2) . ?
C1 C7 1.4827(19) . ?
C2 C3 1.382(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.380(2) . ?
C7 C11 1.414(2) . ?
C8 F1 1.3608(16) . ?
C8 C9 1.389(2) . ?
C9 N1 1.3323(19) . ?
C9 H9 0.9500 . ?
C10 N1 1.3431(18) . ?
C10 N2 1.3502(18) . ?
C10 C11 1.4051(19) . ?
C11 C12 1.4338(19) . ?
C12 N3 1.3258(19) . ?
C12 C13 1.490(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.393(2) . ?
C14 C19 1.396(2) . ?
C14 C20 1.484(2) . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.383(2) . ?
C20 C24 1.4161(19) . ?
C21 F2 1.3583(16) . ?
C21 C22 1.392(2) . ?
C22 N4 1.3264(19) . ?
C22 H22 0.9500 . ?
C23 N4 1.3457(19) . ?
C23 N5 1.3510(18) . ?
C23 C24 1.404(2) . ?
C24 C25 1.432(2) . ?
C25 N6 1.3273(19) . ?
C25 C26 1.489(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.378(2) . ?
C27 C28 1.385(2) . ?
C27 C33 1.486(2) . ?
C28 C29 1.384(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.374(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.364(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.386(2) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.375(2) . ?
C33 C37 1.412(2) . ?
C34 F3 1.3629(17) . ?
C34 C35 1.393(2) . ?
C35 N7 1.326(2) . ?
C35 H35 0.9500 . ?
C36 N7 1.3394(19) . ?
C36 N8 1.3530(19) . ?
C36 C37 1.4096(19) . ?
C37 C38 1.426(2) . ?
C38 N9 1.3268(19) . ?
C38 C39 1.492(2) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
N2 N3 1.3628(17) . ?
N2 H2N 0.897(19) . ?
N5 N6 1.3637(17) . ?
N5 H5N 0.93(2) . ?
N8 N9 1.3637(17) . ?
N8 H8N 0.91(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
C2 C1 C6 119.27(13) . . ?
C2 C1 C7 120.82(13) . . ?
C6 C1 C7 119.87(13) . . ?
C3 C2 C1 120.12(14) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.37(15) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.91(14) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.10(14) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.22(14) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 C11 113.48(13) . . ?
C8 C7 C1 122.17(13) . . ?
C11 C7 C1 124.34(12) . . ?
F1 C8 C7 119.57(12) . . ?
F1 C8 C9 115.93(12) . . ?
C7 C8 C9 124.48(13) . . ?
N1 C9 C8 122.66(13) . . ?
N1 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
N1 C10 N2 125.34(13) . . ?
N1 C10 C11 127.05(13) . . ?
N2 C10 C11 107.59(12) . . ?
C10 C11 C7 118.28(12) . . ?
C10 C11 C12 103.99(12) . . ?
C7 C11 C12 137.68(13) . . ?
N3 C12 C11 110.28(12) . . ?
N3 C12 C13 119.22(13) . . ?
C11 C12 C13 130.48(14) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.53(14) . . ?
C15 C14 C20 121.96(13) . . ?
C19 C14 C20 119.49(13) . . ?
C16 C15 C14 120.57(14) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.52(15) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.45(15) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 120.34(15) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.56(14) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C21 C20 C24 112.99(13) . . ?
C21 C20 C14 122.89(13) . . ?
C24 C20 C14 124.03(13) . . ?
F2 C21 C20 119.69(13) . . ?
F2 C21 C22 116.03(13) . . ?
C20 C21 C22 124.22(13) . . ?
N4 C22 C21 123.42(13) . . ?
N4 C22 H22 118.3 . . ?
C21 C22 H22 118.3 . . ?
N4 C23 N5 124.96(13) . . ?
N4 C23 C24 127.34(13) . . ?
N5 C23 C24 107.66(12) . . ?
C23 C24 C20 118.44(12) . . ?
C23 C24 C25 104.34(12) . . ?
C20 C24 C25 137.17(13) . . ?
N6 C25 C24 109.77(12) . . ?
N6 C25 C26 119.54(13) . . ?
C24 C25 C26 130.55(13) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 118.93(15) . . ?
C32 C27 C33 119.97(14) . . ?
C28 C27 C33 121.10(14) . . ?
C29 C28 C27 120.11(18) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C28 120.47(18) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C31 C30 C29 119.59(17) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C30 C31 C32 120.53(18) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C27 C32 C31 120.36(16) . . ?
C27 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C37 113.39(13) . . ?
C34 C33 C27 122.74(13) . . ?
C37 C33 C27 123.83(13) . . ?
F3 C34 C33 119.46(13) . . ?
F3 C34 C35 116.45(13) . . ?
C33 C34 C35 124.04(14) . . ?
N7 C35 C34 123.58(14) . . ?
N7 C35 H35 118.2 . . ?
C34 C35 H35 118.2 . . ?
N7 C36 N8 125.66(13) . . ?
N7 C36 C37 127.25(13) . . ?
N8 C36 C37 107.08(12) . . ?
C36 C37 C33 118.37(13) . . ?
C36 C37 C38 104.39(12) . . ?
C33 C37 C38 137.19(13) . . ?
N9 C38 C37 110.34(12) . . ?
N9 C38 C39 120.25(14) . . ?
C37 C38 C39 129.38(14) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C9 N1 C10 114.04(12) . . ?
C10 N2 N3 111.04(12) . . ?
C10 N2 H2N 128.3(12) . . ?
N3 N2 H2N 120.7(12) . . ?
C12 N3 N2 107.08(11) . . ?
C22 N4 C23 113.33(12) . . ?
C23 N5 N6 110.58(12) . . ?
C23 N5 H5N 126.7(12) . . ?
N6 N5 H5N 122.3(12) . . ?
C25 N6 N5 107.58(12) . . ?
C35 N7 C36 113.34(12) . . ?
C36 N8 N9 111.15(12) . . ?
C36 N8 H8N 127.9(12) . . ?
N9 N8 H8N 121.0(12) . . ?
C38 N9 N8 107.03(12) . . ?

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
C6 C1 C2 C3 0.7(2) . . . . ?
C7 C1 C2 C3 178.57(13) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C7 C1 C6 C5 -177.92(13) . . . . ?
C2 C1 C7 C8 -52.55(19) . . . . ?
C6 C1 C7 C8 125.29(15) . . . . ?
C2 C1 C7 C11 128.93(15) . . . . ?
C6 C1 C7 C11 -53.22(19) . . . . ?
C11 C7 C8 F1 179.20(11) . . . . ?
C1 C7 C8 F1 0.5(2) . . . . ?
C11 C7 C8 C9 0.9(2) . . . . ?
C1 C7 C8 C9 -177.79(14) . . . . ?
F1 C8 C9 N1 -179.10(13) . . . . ?
C7 C8 C9 N1 -0.7(2) . . . . ?
N1 C10 C11 C7 0.8(2) . . . . ?
N2 C10 C11 C7 179.17(12) . . . . ?
N1 C10 C11 C12 -177.21(13) . . . . ?
N2 C10 C11 C12 1.11(15) . . . . ?
C8 C7 C11 C10 -0.89(18) . . . . ?
C1 C7 C11 C10 177.74(13) . . . . ?
C8 C7 C11 C12 176.31(16) . . . . ?
C1 C7 C11 C12 -5.1(3) . . . . ?
C10 C11 C12 N3 -0.94(15) . . . . ?
C7 C11 C12 N3 -178.40(15) . . . . ?
C10 C11 C12 C13 177.14(15) . . . . ?
C7 C11 C12 C13 -0.3(3) . . . . ?
C19 C14 C15 C16 2.1(2) . . . . ?
C20 C14 C15 C16 -179.59(14) . . . . ?
C14 C15 C16 C17 -1.2(2) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 C19 1.1(3) . . . . ?
C17 C18 C19 C14 -0.2(2) . . . . ?
C15 C14 C19 C18 -1.4(2) . . . . ?
C20 C14 C19 C18 -179.73(14) . . . . ?
C15 C14 C20 C21 -47.9(2) . . . . ?
C19 C14 C20 C21 130.45(15) . . . . ?
C15 C14 C20 C24 135.90(15) . . . . ?
C19 C14 C20 C24 -45.8(2) . . . . ?
C24 C20 C21 F2 -178.05(12) . . . . ?
C14 C20 C21 F2 5.3(2) . . . . ?
C24 C20 C21 C22 4.9(2) . . . . ?
C14 C20 C21 C22 -171.74(14) . . . . ?
F2 C21 C22 N4 -178.25(13) . . . . ?
C20 C21 C22 N4 -1.1(2) . . . . ?
N4 C23 C24 C20 2.7(2) . . . . ?
N5 C23 C24 C20 -179.52(12) . . . . ?
N4 C23 C24 C25 -175.05(14) . . . . ?
N5 C23 C24 C25 2.71(15) . . . . ?
C21 C20 C24 C23 -5.40(19) . . . . ?
C14 C20 C24 C23 171.17(13) . . . . ?
C21 C20 C24 C25 171.41(16) . . . . ?
C14 C20 C24 C25 -12.0(3) . . . . ?
C23 C24 C25 N6 -2.35(16) . . . . ?
C20 C24 C25 N6 -179.47(15) . . . . ?
C23 C24 C25 C26 173.10(15) . . . . ?
C20 C24 C25 C26 -4.0(3) . . . . ?
C32 C27 C28 C29 -1.1(3) . . . . ?
C33 C27 C28 C29 179.45(19) . . . . ?
C27 C28 C29 C30 0.8(4) . . . . ?
C28 C29 C30 C31 -0.1(4) . . . . ?
C29 C30 C31 C32 -0.3(4) . . . . ?
C28 C27 C32 C31 0.7(3) . . . . ?
C33 C27 C32 C31 -179.87(17) . . . . ?
C30 C31 C32 C27 0.0(3) . . . . ?
C32 C27 C33 C34 -116.81(18) . . . . ?
C28 C27 C33 C34 62.6(2) . . . . ?
C32 C27 C33 C37 60.9(2) . . . . ?
C28 C27 C33 C37 -119.71(18) . . . . ?
C37 C33 C34 F3 -179.57(13) . . . . ?
C27 C33 C34 F3 -1.7(2) . . . . ?
C37 C33 C34 C35 -2.1(2) . . . . ?
C27 C33 C34 C35 175.76(15) . . . . ?
F3 C34 C35 N7 179.00(14) . . . . ?
C33 C34 C35 N7 1.5(3) . . . . ?
N7 C36 C37 C33 0.0(2) . . . . ?
N8 C36 C37 C33 -178.61(12) . . . . ?
N7 C36 C37 C38 177.92(14) . . . . ?
N8 C36 C37 C38 -0.68(15) . . . . ?
C34 C33 C37 C36 1.39(19) . . . . ?
C27 C33 C37 C36 -176.46(13) . . . . ?
C34 C33 C37 C38 -175.66(16) . . . . ?
C27 C33 C37 C38 6.5(3) . . . . ?
C36 C37 C38 N9 0.51(16) . . . . ?
C33 C37 C38 N9 177.84(16) . . . . ?
C36 C37 C38 C39 -177.73(16) . . . . ?
C33 C37 C38 C39 -0.4(3) . . . . ?
C8 C9 N1 C10 0.5(2) . . . . ?
N2 C10 N1 C9 -178.64(13) . . . . ?
C11 C10 N1 C9 -0.6(2) . . . . ?
N1 C10 N2 N3 177.42(13) . . . . ?
C11 C10 N2 N3 -0.95(16) . . . . ?
C11 C12 N3 N2 0.40(15) . . . . ?
C13 C12 N3 N2 -177.93(13) . . . . ?
C10 N2 N3 C12 0.34(16) . . . . ?
C21 C22 N4 C23 -2.1(2) . . . . ?
N5 C23 N4 C22 -176.13(14) . . . . ?
C24 C23 N4 C22 1.3(2) . . . . ?
N4 C23 N5 N6 175.60(13) . . . . ?
C24 C23 N5 N6 -2.23(16) . . . . ?
C24 C25 N6 N5 1.07(16) . . . . ?
C26 C25 N6 N5 -174.96(13) . . . . ?
C23 N5 N6 C25 0.72(16) . . . . ?
C34 C35 N7 C36 0.1(2) . . . . ?
N8 C36 N7 C35 177.59(14) . . . . ?
C37 C36 N7 C35 -0.7(2) . . . . ?
N7 C36 N8 N9 -177.99(13) . . . . ?
C37 C36 N8 N9 0.63(16) . . . . ?
C37 C38 N9 N8 -0.15(16) . . . . ?
C39 C38 N9 N8 178.29(14) . . . . ?
C36 N8 N9 C38 -0.31(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N N4 0.897(19) 2.09(2) 2.9531(18) 162.4(16) .
N5 H5N N1 0.93(2) 1.94(2) 2.8549(17) 167.2(17) .
N8 H8N N6 0.91(2) 2.08(2) 2.9935(18) 174.4(17) .

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.062



