# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cd15293
_database_code_depnum_ccdc_archive 'CCDC 1440522'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 F3 N3'
_chemical_formula_weight         417.42

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'
F F 0.0171 0.0103 '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                   21.381(8)
_cell_length_b                   12.571(4)
_cell_length_c                   16.690(6)
_cell_angle_alpha                90
_cell_angle_beta                 117.251(8)
_cell_angle_gamma                90
_cell_volume                     3988(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1616
_cell_measurement_theta_min      5.297
_cell_measurement_theta_max      40.879

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6357
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11038
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.942
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3920
_reflns_number_gt                2605
_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 SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0593P)²+0.9045P] 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         3920
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
F1 F 0.13240(10) 0.21091(17) -0.03875(11) 0.1185(7) Uani 1 1 d . . . . .
F2 F 0.07134(8) 0.19103(16) 0.02797(13) 0.1159(7) Uani 1 1 d . . . . .
F3 F 0.10580(9) 0.34311(12) 0.01508(12) 0.1048(6) Uani 1 1 d . . . . .
N1 N 0.20747(8) 0.04359(13) 0.07632(11) 0.0434(4) Uani 1 1 d . . . . .
N2 N 0.23982(9) 0.04750(14) 0.02424(12) 0.0516(5) Uani 1 1 d . . . . .
N3 N 0.21637(9) -0.03475(14) -0.03000(11) 0.0519(5) Uani 1 1 d . . . . .
C1 C 0.16939(10) -0.09040(16) -0.01268(13) 0.0445(5) Uani 1 1 d . . . . .
C2 C 0.16416(10) -0.04043(15) 0.05688(13) 0.0422(5) Uani 1 1 d . . . . .
C3 C 0.13177(10) -0.03639(16) 0.11615(13) 0.0440(5) Uani 1 1 d . . . . .
C4 C 0.08423(12) -0.10287(19) 0.12545(15) 0.0595(6) Uani 1 1 d . . . . .
H4 H 0.0692 -0.1650 0.0918 0.071 Uiso 1 1 calc R U . . .
C5 C 0.05959(13) -0.0755(2) 0.18537(17) 0.0729(8) Uani 1 1 d . . . . .
H5 H 0.0279 -0.1199 0.1929 0.087 Uiso 1 1 calc R U . . .
C6 C 0.08114(13) 0.0169(2) 0.23434(17) 0.0686(7) Uani 1 1 d . . . . .
H6 H 0.0634 0.0347 0.2741 0.082 Uiso 1 1 calc R U . . .
C7 C 0.12844(11) 0.08329(19) 0.22551(15) 0.0559(6) Uani 1 1 d . . . . .
H7 H 0.1420 0.1465 0.2579 0.067 Uiso 1 1 calc R U . . .
C8 C 0.15553(10) 0.05518(16) 0.16826(13) 0.0442(5) Uani 1 1 d . . . . .
C9 C 0.21107(10) 0.11254(15) 0.15055(13) 0.0418(5) Uani 1 1 d . . . . .
C10 C 0.19042(11) 0.22806(16) 0.11884(14) 0.0480(5) Uani 1 1 d . . . . .
C11 C 0.24375(14) 0.31429(18) 0.13892(18) 0.0642(7) Uani 1 1 d . . . . .
H11A H 0.2930 0.2946 0.1702 0.077 Uiso 1 1 calc R U . . .
H11B H 0.2329 0.3705 0.0947 0.077 Uiso 1 1 calc R U . . .
C12 C 0.20312(13) 0.31070(17) 0.18998(17) 0.0618(6) Uani 1 1 d . . . . .
H12A H 0.1672 0.3645 0.1769 0.074 Uiso 1 1 calc R U . . .
H12B H 0.2274 0.2886 0.2525 0.074 Uiso 1 1 calc R U . . .
C13 C 0.12567(14) 0.2426(2) 0.03253(19) 0.0672(7) Uani 1 1 d . . . . .
C14 C 0.28439(10) 0.10514(15) 0.23085(14) 0.0441(5) Uani 1 1 d . . . . .
C15 C 0.34311(12) 0.11126(17) 0.21717(17) 0.0595(6) Uani 1 1 d . . . . .
H15 H 0.3381 0.1187 0.1591 0.071 Uiso 1 1 calc R U . . .
C16 C 0.40947(13) 0.1063(2) 0.2896(2) 0.0772(8) Uani 1 1 d . . . . .
H16 H 0.4490 0.1108 0.2800 0.093 Uiso 1 1 calc R U . . .
C17 C 0.41749(15) 0.0949(2) 0.3756(2) 0.0787(8) Uani 1 1 d . . . . .
H17 H 0.4623 0.0916 0.4242 0.094 Uiso 1 1 calc R U . . .
C18 C 0.36019(14) 0.08837(19) 0.38963(17) 0.0697(7) Uani 1 1 d . . . . .
H18 H 0.3656 0.0805 0.4478 0.084 Uiso 1 1 calc R U . . .
C19 C 0.29393(12) 0.09340(16) 0.31794(15) 0.0532(6) Uani 1 1 d . . . . .
H19 H 0.2548 0.0888 0.3283 0.064 Uiso 1 1 calc R U . . .
C20 C 0.13451(11) -0.18701(16) -0.06232(13) 0.0477(5) Uani 1 1 d . . . . .
C21 C 0.06703(12) -0.21061(19) -0.07943(15) 0.0613(6) Uani 1 1 d . . . . .
H21 H 0.0420 -0.1629 -0.0625 0.074 Uiso 1 1 calc R U . . .
C22 C 0.03595(14) -0.3042(2) -0.12139(17) 0.0772(8) Uani 1 1 d . . . . .
H22 H -0.0097 -0.3202 -0.1322 0.093 Uiso 1 1 calc R U . . .
C23 C 0.07284(17) -0.3742(2) -0.14725(17) 0.0780(8) Uani 1 1 d . . . . .
H23 H 0.0525 -0.4385 -0.1742 0.094 Uiso 1 1 calc R U . . .
C24 C 0.13871(15) -0.34992(19) -0.13372(15) 0.0674(7) Uani 1 1 d . . . . .
H24 H 0.1628 -0.3965 -0.1531 0.081 Uiso 1 1 calc R U . . .
C25 C 0.17006(13) -0.25666(18) -0.09139(14) 0.0547(6) Uani 1 1 d . . . . .
H25 H 0.2153 -0.2403 -0.0823 0.066 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.324(3) . ?
F2 C13 1.302(3) . ?
F3 C13 1.322(3) . ?
N1 N2 1.337(2) . ?
N1 C2 1.343(2) . ?
N1 C9 1.485(2) . ?
N2 N3 1.313(2) . ?
N3 C1 1.359(2) . ?
C1 C2 1.369(3) . ?
C1 C20 1.467(3) . ?
C2 C3 1.445(3) . ?
C3 C4 1.379(3) . ?
C3 C8 1.391(3) . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.529(3) . ?
C9 C14 1.529(3) . ?
C9 C10 1.540(3) . ?
C10 C13 1.483(3) . ?
C10 C11 1.496(3) . ?
C10 C12 1.506(3) . ?
C11 C12 1.470(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C15 1.377(3) . ?
C14 C19 1.380(3) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.351(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.369(3) . ?
C20 C25 1.385(3) . ?
C21 C22 1.375(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.376(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.355(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.375(3) . ?
C24 H24 0.9300 . ?
C25 H25 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
N2 N1 C2 112.13(16) . . ?
N2 N1 C9 132.56(16) . . ?
C2 N1 C9 115.30(16) . . ?
N3 N2 N1 105.75(16) . . ?
N2 N3 C1 110.16(16) . . ?
N3 C1 C2 107.43(17) . . ?
N3 C1 C20 122.68(18) . . ?
C2 C1 C20 129.88(19) . . ?
N1 C2 C1 104.53(17) . . ?
N1 C2 C3 107.49(16) . . ?
C1 C2 C3 147.95(19) . . ?
C4 C3 C8 120.55(19) . . ?
C4 C3 C2 131.68(19) . . ?
C8 C3 C2 107.75(17) . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.1(2) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C7 C8 C3 119.94(19) . . ?
C7 C8 C9 128.78(18) . . ?
C3 C8 C9 111.28(17) . . ?
N1 C9 C14 109.66(15) . . ?
N1 C9 C8 97.92(15) . . ?
C14 C9 C8 112.16(16) . . ?
N1 C9 C10 111.51(16) . . ?
C14 C9 C10 112.10(15) . . ?
C8 C9 C10 112.66(16) . . ?
C13 C10 C11 113.9(2) . . ?
C13 C10 C12 115.60(19) . . ?
C11 C10 C12 58.65(15) . . ?
C13 C10 C9 116.33(18) . . ?
C11 C10 C9 122.50(19) . . ?
C12 C10 C9 117.38(18) . . ?
C12 C11 C10 61.01(15) . . ?
C12 C11 H11A 117.7 . . ?
C10 C11 H11A 117.7 . . ?
C12 C11 H11B 117.7 . . ?
C10 C11 H11B 117.7 . . ?
H11A C11 H11B 114.8 . . ?
C11 C12 C10 60.34(15) . . ?
C11 C12 H12A 117.7 . . ?
C10 C12 H12A 117.7 . . ?
C11 C12 H12B 117.7 . . ?
C10 C12 H12B 117.7 . . ?
H12A C12 H12B 114.9 . . ?
F2 C13 F3 106.0(2) . . ?
F2 C13 F1 105.0(2) . . ?
F3 C13 F1 104.2(2) . . ?
F2 C13 C10 114.0(2) . . ?
F3 C13 C10 113.2(2) . . ?
F1 C13 C10 113.5(2) . . ?
C15 C14 C19 118.3(2) . . ?
C15 C14 C9 119.9(2) . . ?
C19 C14 C9 121.82(19) . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
C21 C20 C25 119.0(2) . . ?
C21 C20 C1 120.8(2) . . ?
C25 C20 C1 120.2(2) . . ?
C20 C21 C22 120.6(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C23 119.6(3) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.2(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 N2 N3 0.6(2) . . . . ?
C9 N1 N2 N3 179.79(18) . . . . ?
N1 N2 N3 C1 0.1(2) . . . . ?
N2 N3 C1 C2 -0.8(2) . . . . ?
N2 N3 C1 C20 -179.62(17) . . . . ?
N2 N1 C2 C1 -1.0(2) . . . . ?
C9 N1 C2 C1 179.62(16) . . . . ?
N2 N1 C2 C3 -179.52(16) . . . . ?
C9 N1 C2 C3 1.1(2) . . . . ?
N3 C1 C2 N1 1.0(2) . . . . ?
C20 C1 C2 N1 179.81(19) . . . . ?
N3 C1 C2 C3 178.3(3) . . . . ?
C20 C1 C2 C3 -2.9(5) . . . . ?
N1 C2 C3 C4 -179.2(2) . . . . ?
C1 C2 C3 C4 3.5(5) . . . . ?
N1 C2 C3 C8 2.4(2) . . . . ?
C1 C2 C3 C8 -174.9(3) . . . . ?
C8 C3 C4 C5 1.6(3) . . . . ?
C2 C3 C4 C5 -176.6(2) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
C5 C6 C7 C8 -1.5(4) . . . . ?
C6 C7 C8 C3 3.8(3) . . . . ?
C6 C7 C8 C9 -176.7(2) . . . . ?
C4 C3 C8 C7 -4.0(3) . . . . ?
C2 C3 C8 C7 174.66(19) . . . . ?
C4 C3 C8 C9 176.52(19) . . . . ?
C2 C3 C8 C9 -4.9(2) . . . . ?
N2 N1 C9 C14 -65.9(3) . . . . ?
C2 N1 C9 C14 113.32(18) . . . . ?
N2 N1 C9 C8 177.13(19) . . . . ?
C2 N1 C9 C8 -3.7(2) . . . . ?
N2 N1 C9 C10 58.9(3) . . . . ?
C2 N1 C9 C10 -121.92(18) . . . . ?
C7 C8 C9 N1 -174.4(2) . . . . ?
C3 C8 C9 N1 5.1(2) . . . . ?
C7 C8 C9 C14 70.5(3) . . . . ?
C3 C8 C9 C14 -109.99(19) . . . . ?
C7 C8 C9 C10 -57.1(3) . . . . ?
C3 C8 C9 C10 122.40(18) . . . . ?
N1 C9 C10 C13 46.9(2) . . . . ?
C14 C9 C10 C13 170.27(19) . . . . ?
C8 C9 C10 C13 -62.1(2) . . . . ?
N1 C9 C10 C11 -101.5(2) . . . . ?
C14 C9 C10 C11 21.9(3) . . . . ?
C8 C9 C10 C11 149.6(2) . . . . ?
N1 C9 C10 C12 -170.06(17) . . . . ?
C14 C9 C10 C12 -46.7(2) . . . . ?
C8 C9 C10 C12 81.0(2) . . . . ?
C13 C10 C11 C12 106.5(2) . . . . ?
C9 C10 C11 C12 -104.5(2) . . . . ?
C13 C10 C12 C11 -103.5(2) . . . . ?
C9 C10 C12 C11 113.1(2) . . . . ?
C11 C10 C13 F2 -158.6(2) . . . . ?
C12 C10 C13 F2 -93.3(3) . . . . ?
C9 C10 C13 F2 50.4(3) . . . . ?
C11 C10 C13 F3 -37.3(3) . . . . ?
C12 C10 C13 F3 27.9(3) . . . . ?
C9 C10 C13 F3 171.6(2) . . . . ?
C11 C10 C13 F1 81.2(3) . . . . ?
C12 C10 C13 F1 146.5(2) . . . . ?
C9 C10 C13 F1 -69.8(3) . . . . ?
N1 C9 C14 C15 45.7(2) . . . . ?
C8 C9 C14 C15 153.38(18) . . . . ?
C10 C9 C14 C15 -78.7(2) . . . . ?
N1 C9 C14 C19 -134.93(19) . . . . ?
C8 C9 C14 C19 -27.3(3) . . . . ?
C10 C9 C14 C19 100.6(2) . . . . ?
C19 C14 C15 C16 -0.4(3) . . . . ?
C9 C14 C15 C16 179.0(2) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C17 C18 C19 C14 0.0(3) . . . . ?
C15 C14 C19 C18 0.3(3) . . . . ?
C9 C14 C19 C18 -179.06(19) . . . . ?
N3 C1 C20 C21 -146.3(2) . . . . ?
C2 C1 C20 C21 35.1(3) . . . . ?
N3 C1 C20 C25 34.7(3) . . . . ?
C2 C1 C20 C25 -143.9(2) . . . . ?
C25 C20 C21 C22 2.8(3) . . . . ?
C1 C20 C21 C22 -176.2(2) . . . . ?
C20 C21 C22 C23 -0.7(4) . . . . ?
C21 C22 C23 C24 -1.8(4) . . . . ?
C22 C23 C24 C25 2.1(4) . . . . ?
C23 C24 C25 C20 0.0(3) . . . . ?
C21 C20 C25 C24 -2.5(3) . . . . ?
C1 C20 C25 C24 176.57(19) . . . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd16297
_database_code_depnum_ccdc_archive 'CCDC 1482939'
_audit_update_record             
;
2016-06-01 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H32 N12'
_chemical_formula_weight         728.81

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   8.1858(10)
_cell_length_b                   10.1508(13)
_cell_length_c                   22.150(3)
_cell_angle_alpha                89.880(3)
_cell_angle_beta                 83.440(3)
_cell_angle_gamma                78.898(3)
_cell_volume                     1793.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1203
_cell_measurement_theta_min      5.106
_cell_measurement_theta_max      40.944

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10435
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.851
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6666
_reflns_number_gt                4047
_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 SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0761P)²+0.0125P] 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         6666
_refine_ls_number_parameters     505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1446
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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
N1 N 0.8402(3) 0.0685(2) 0.35888(9) 0.0380(6) Uani 1 1 d . . . . .
N2 N 0.7614(3) 0.1871(2) 0.34045(10) 0.0455(6) Uani 1 1 d . . . . .
N3 N 0.6596(3) 0.2409(2) 0.38793(11) 0.0467(6) Uani 1 1 d . . . . .
N4 N 0.8643(3) -0.0048(3) 0.22785(11) 0.0565(7) Uani 1 1 d . . . . .
N5 N 0.8219(3) -0.0489(2) 0.18233(11) 0.0472(6) Uani 1 1 d . . . . .
N6 N 0.7774(4) -0.0747(3) 0.13821(13) 0.0722(9) Uani 1 1 d . . . . .
N7 N 0.0969(3) 0.5608(2) 0.14532(9) 0.0371(5) Uani 1 1 d . . . . .
N8 N 0.1149(3) 0.6798(2) 0.16670(10) 0.0448(6) Uani 1 1 d . . . . .
N9 N 0.1919(3) 0.7363(2) 0.12115(11) 0.0447(6) Uani 1 1 d . . . . .
N10 N 0.1107(3) 0.4856(3) 0.27650(11) 0.0570(7) Uani 1 1 d . . . . .
N11 N 0.0389(3) 0.4539(3) 0.32423(12) 0.0527(7) Uani 1 1 d . . . . .
N12 N -0.0248(5) 0.4365(3) 0.37023(14) 0.0848(10) Uani 1 1 d . . . . .
C1 C 0.8945(3) -0.0848(3) 0.43164(11) 0.0372(6) Uani 1 1 d . . . . .
C2 C 0.9033(4) -0.1601(3) 0.48332(13) 0.0528(8) Uani 1 1 d . . . . .
H2 H 0.8331 -0.1306 0.5187 0.063 Uiso 1 1 calc R U . . .
C3 C 1.0167(4) -0.2795(3) 0.48218(14) 0.0594(9) Uani 1 1 d . . . . .
H3 H 1.0230 -0.3302 0.5171 0.071 Uiso 1 1 calc R U . . .
C4 C 1.1211(4) -0.3251(3) 0.43013(14) 0.0540(8) Uani 1 1 d . . . . .
H4 H 1.1974 -0.4059 0.4303 0.065 Uiso 1 1 calc R U . . .
C5 C 1.1126(4) -0.2513(3) 0.37784(13) 0.0480(8) Uani 1 1 d . . . . .
H5 H 1.1828 -0.2817 0.3426 0.058 Uiso 1 1 calc R U . . .
C6 C 0.9987(3) -0.1316(3) 0.37839(12) 0.0379(7) Uani 1 1 d . . . . .
C7 C 0.9714(3) -0.0351(3) 0.32595(11) 0.0379(7) Uani 1 1 d . . . . .
C8 C 0.8986(4) -0.1019(3) 0.27658(12) 0.0438(7) Uani 1 1 d . . . . .
H8A H 0.9775 -0.1812 0.2604 0.053 Uiso 1 1 calc R U . . .
H8B H 0.7958 -0.1292 0.2933 0.053 Uiso 1 1 calc R U . . .
C9 C 0.7933(3) 0.0451(3) 0.41793(11) 0.0372(7) Uani 1 1 d . . . . .
C10 C 0.6742(3) 0.1577(3) 0.43650(12) 0.0392(7) Uani 1 1 d . . . . .
C11 C 0.5748(3) 0.2004(3) 0.49515(13) 0.0435(7) Uani 1 1 d . . . . .
C12 C 0.4720(5) 0.3248(4) 0.50130(16) 0.0714(11) Uani 1 1 d . . . . .
H12 H 0.4611 0.3793 0.4676 0.086 Uiso 1 1 calc R U . . .
C13 C 0.3845(5) 0.3701(4) 0.55686(19) 0.0862(13) Uani 1 1 d . . . . .
H13 H 0.3162 0.4549 0.5601 0.103 Uiso 1 1 calc R U . . .
C14 C 0.3970(4) 0.2922(4) 0.60705(16) 0.0678(10) Uani 1 1 d . . . . .
H14 H 0.3397 0.3240 0.6445 0.081 Uiso 1 1 calc R U . . .
C15 C 0.4946(4) 0.1673(4) 0.60132(14) 0.0636(10) Uani 1 1 d . . . . .
H15 H 0.5027 0.1124 0.6349 0.076 Uiso 1 1 calc R U . . .
C16 C 0.5817(4) 0.1217(4) 0.54598(14) 0.0569(9) Uani 1 1 d . . . . .
H16 H 0.6468 0.0356 0.5428 0.068 Uiso 1 1 calc R U . . .
C17 C 1.1288(3) 0.0189(3) 0.30491(12) 0.0405(7) Uani 1 1 d . . . . .
C18 C 1.1768(4) 0.1141(3) 0.34029(13) 0.0458(7) Uani 1 1 d . . . . .
H18 H 1.1081 0.1481 0.3754 0.055 Uiso 1 1 calc R U . . .
C19 C 1.3230(4) 0.1594(3) 0.32481(15) 0.0562(9) Uani 1 1 d . . . . .
H19 H 1.3529 0.2230 0.3494 0.067 Uiso 1 1 calc R U . . .
C20 C 1.4253(4) 0.1109(3) 0.27292(16) 0.0596(9) Uani 1 1 d . . . . .
H20 H 1.5251 0.1407 0.2623 0.071 Uiso 1 1 calc R U . . .
C21 C 1.3785(4) 0.0176(4) 0.23674(16) 0.0643(10) Uani 1 1 d . . . . .
H21 H 1.4466 -0.0146 0.2013 0.077 Uiso 1 1 calc R U . . .
C22 C 1.2316(4) -0.0287(3) 0.25252(14) 0.0534(8) Uani 1 1 d . . . . .
H22 H 1.2018 -0.0921 0.2278 0.064 Uiso 1 1 calc R U . . .
C23 C 0.1300(3) 0.4065(3) 0.06915(12) 0.0379(7) Uani 1 1 d . . . . .
C24 C 0.1659(4) 0.3296(3) 0.01573(13) 0.0494(8) Uani 1 1 d . . . . .
H24 H 0.2181 0.3620 -0.0191 0.059 Uiso 1 1 calc R U . . .
C25 C 0.1230(4) 0.2047(3) 0.01504(14) 0.0578(9) Uani 1 1 d . . . . .
H25 H 0.1451 0.1536 -0.0208 0.069 Uiso 1 1 calc R U . . .
C26 C 0.0483(4) 0.1543(3) 0.06640(15) 0.0560(8) Uani 1 1 d . . . . .
H26 H 0.0229 0.0690 0.0652 0.067 Uiso 1 1 calc R U . . .
C27 C 0.0107(4) 0.2295(3) 0.11974(14) 0.0511(8) Uani 1 1 d . . . . .
H27 H -0.0412 0.1961 0.1544 0.061 Uiso 1 1 calc R U . . .
C28 C 0.0517(3) 0.3549(3) 0.12063(12) 0.0377(6) Uani 1 1 d . . . . .
C29 C 0.0202(3) 0.4533(3) 0.17461(11) 0.0379(7) Uani 1 1 d . . . . .
C30 C 0.1242(4) 0.3913(3) 0.22488(12) 0.0486(8) Uani 1 1 d . . . . .
H30A H 0.0858 0.3109 0.2392 0.058 Uiso 1 1 calc R U . . .
H30B H 0.2409 0.3654 0.2081 0.058 Uiso 1 1 calc R U . . .
C31 C 0.1600(3) 0.5391(3) 0.08622(11) 0.0353(6) Uani 1 1 d . . . . .
C32 C 0.2231(3) 0.6532(3) 0.07089(12) 0.0381(7) Uani 1 1 d . . . . .
C33 C 0.3074(3) 0.6955(3) 0.01372(12) 0.0396(7) Uani 1 1 d . . . . .
C34 C 0.3480(4) 0.8225(3) 0.01028(15) 0.0579(9) Uani 1 1 d . . . . .
H34 H 0.3237 0.8796 0.0442 0.069 Uiso 1 1 calc R U . . .
C35 C 0.4236(5) 0.8639(4) -0.04295(15) 0.0668(10) Uani 1 1 d . . . . .
H35 H 0.4483 0.9495 -0.0447 0.080 Uiso 1 1 calc R U . . .
C36 C 0.4631(4) 0.7819(4) -0.09338(14) 0.0578(9) Uani 1 1 d . . . . .
H36 H 0.5150 0.8108 -0.1292 0.069 Uiso 1 1 calc R U . . .
C37 C 0.4251(4) 0.6565(4) -0.09026(14) 0.0614(9) Uani 1 1 d . . . . .
H37 H 0.4511 0.5993 -0.1242 0.074 Uiso 1 1 calc R U . . .
C38 C 0.3489(4) 0.6148(3) -0.03739(14) 0.0608(9) Uani 1 1 d . . . . .
H38 H 0.3245 0.5289 -0.0361 0.073 Uiso 1 1 calc R U . . .
C39 C -0.1654(3) 0.5012(3) 0.19544(12) 0.0392(7) Uani 1 1 d . . . . .
C40 C -0.2559(4) 0.6114(3) 0.16865(13) 0.0476(8) Uani 1 1 d . . . . .
H40 H -0.2015 0.6592 0.1396 0.057 Uiso 1 1 calc R U . . .
C41 C -0.4267(4) 0.6502(3) 0.18511(16) 0.0585(9) Uani 1 1 d . . . . .
H41 H -0.4872 0.7216 0.1657 0.070 Uiso 1 1 calc R U . . .
C42 C -0.5074(4) 0.5846(4) 0.22962(16) 0.0622(10) Uani 1 1 d . . . . .
H42 H -0.6213 0.6137 0.2416 0.075 Uiso 1 1 calc R U . . .
C43 C -0.4191(4) 0.4749(4) 0.25668(15) 0.0615(9) Uani 1 1 d . . . . .
H43 H -0.4739 0.4289 0.2864 0.074 Uiso 1 1 calc R U . . .
C44 C -0.2494(4) 0.4336(3) 0.23951(13) 0.0503(8) Uani 1 1 d . . . . .
H44 H -0.1907 0.3594 0.2577 0.060 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 N2 1.338(3) . ?
N1 C9 1.354(3) . ?
N1 C7 1.477(3) . ?
N2 N3 1.314(3) . ?
N3 C10 1.368(4) . ?
N4 N5 1.216(3) . ?
N4 C8 1.474(4) . ?
N5 N6 1.129(3) . ?
N7 N8 1.339(3) . ?
N7 C31 1.354(3) . ?
N7 C29 1.474(3) . ?
N8 N9 1.318(3) . ?
N9 C32 1.368(3) . ?
N10 N11 1.223(4) . ?
N10 C30 1.474(4) . ?
N11 N12 1.120(4) . ?
C1 C2 1.376(4) . ?
C1 C6 1.400(3) . ?
C1 C9 1.467(4) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.526(4) . ?
C7 C17 1.521(4) . ?
C7 C8 1.523(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.381(4) . ?
C10 C11 1.471(4) . ?
C11 C12 1.374(4) . ?
C11 C16 1.379(4) . ?
C12 C13 1.383(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.382(4) . ?
C17 C18 1.387(4) . ?
C18 C19 1.371(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.390(4) . ?
C23 C28 1.395(4) . ?
C23 C31 1.472(4) . ?
C24 C25 1.380(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.374(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.379(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.378(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.526(4) . ?
C29 C39 1.521(4) . ?
C29 C30 1.539(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.383(4) . ?
C32 C33 1.476(4) . ?
C33 C38 1.370(4) . ?
C33 C34 1.391(4) . ?
C34 C35 1.371(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.365(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.367(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.369(4) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C44 1.386(4) . ?
C39 C40 1.389(4) . ?
C40 C41 1.384(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.367(5) . ?
C41 H41 0.9300 . ?
C42 C43 1.381(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.380(4) . ?
C43 H43 0.9300 . ?
C44 H44 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
N2 N1 C9 113.0(2) . . ?
N2 N1 C7 130.3(2) . . ?
C9 N1 C7 116.7(2) . . ?
N3 N2 N1 105.4(2) . . ?
N2 N3 C10 110.5(2) . . ?
N5 N4 C8 115.7(2) . . ?
N6 N5 N4 172.0(3) . . ?
N8 N7 C31 112.5(2) . . ?
N8 N7 C29 131.3(2) . . ?
C31 N7 C29 116.2(2) . . ?
N9 N8 N7 106.0(2) . . ?
N8 N9 C32 110.0(2) . . ?
N11 N10 C30 115.5(3) . . ?
N12 N11 N10 173.2(3) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 C9 133.2(3) . . ?
C6 C1 C9 107.1(2) . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 C7 127.3(2) . . ?
C1 C6 C7 112.3(2) . . ?
N1 C7 C6 97.6(2) . . ?
N1 C7 C17 111.8(2) . . ?
C6 C7 C17 111.4(2) . . ?
N1 C7 C8 110.0(2) . . ?
C6 C7 C8 109.2(2) . . ?
C17 C7 C8 115.3(2) . . ?
N4 C8 C7 108.5(2) . . ?
N4 C8 H8A 110.0 . . ?
C7 C8 H8A 110.0 . . ?
N4 C8 H8B 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N1 C9 C10 103.6(2) . . ?
N1 C9 C1 106.4(2) . . ?
C10 C9 C1 150.0(3) . . ?
N3 C10 C9 107.5(2) . . ?
N3 C10 C11 119.6(3) . . ?
C9 C10 C11 132.9(3) . . ?
C12 C11 C16 117.2(3) . . ?
C12 C11 C10 119.9(3) . . ?
C16 C11 C10 122.9(3) . . ?
C11 C12 C13 120.9(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 118.8(3) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 121.7(3) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
C22 C17 C18 118.2(3) . . ?
C22 C17 C7 122.0(3) . . ?
C18 C17 C7 119.8(2) . . ?
C19 C18 C17 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 119.3(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C22 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C17 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C24 C23 C28 118.9(3) . . ?
C24 C23 C31 133.6(3) . . ?
C28 C23 C31 107.4(2) . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 121.2(3) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C27 120.5(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C28 118.7(3) . . ?
C26 C27 H27 120.7 . . ?
C28 C27 H27 120.7 . . ?
C27 C28 C23 121.5(3) . . ?
C27 C28 C29 126.8(3) . . ?
C23 C28 C29 111.7(2) . . ?
N7 C29 C39 111.9(2) . . ?
N7 C29 C28 98.3(2) . . ?
C39 C29 C28 112.6(2) . . ?
N7 C29 C30 109.4(2) . . ?
C39 C29 C30 114.5(2) . . ?
C28 C29 C30 109.0(2) . . ?
N10 C30 C29 111.9(2) . . ?
N10 C30 H30A 109.2 . . ?
C29 C30 H30A 109.2 . . ?
N10 C30 H30B 109.2 . . ?
C29 C30 H30B 109.2 . . ?
H30A C30 H30B 107.9 . . ?
N7 C31 C32 103.9(2) . . ?
N7 C31 C23 106.3(2) . . ?
C32 C31 C23 149.8(2) . . ?
N9 C32 C31 107.6(2) . . ?
N9 C32 C33 120.0(3) . . ?
C31 C32 C33 132.4(2) . . ?
C38 C33 C34 117.3(3) . . ?
C38 C33 C32 122.9(3) . . ?
C34 C33 C32 119.8(3) . . ?
C35 C34 C33 120.3(3) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C34 121.3(3) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C35 C36 C37 118.7(3) . . ?
C35 C36 H36 120.6 . . ?
C37 C36 H36 120.6 . . ?
C36 C37 C38 120.3(3) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C33 C38 C37 122.0(3) . . ?
C33 C38 H38 119.0 . . ?
C37 C38 H38 119.0 . . ?
C44 C39 C40 118.5(3) . . ?
C44 C39 C29 121.2(3) . . ?
C40 C39 C29 120.2(3) . . ?
C41 C40 C39 120.2(3) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C42 C41 C40 120.7(3) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C41 C42 C43 119.7(3) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C44 C43 C42 119.9(3) . . ?
C44 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
C43 C44 C39 120.9(3) . . ?
C43 C44 H44 119.5 . . ?
C39 C44 H44 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 N2 N3 -1.0(3) . . . . ?
C7 N1 N2 N3 -178.5(2) . . . . ?
N1 N2 N3 C10 0.4(3) . . . . ?
C31 N7 N8 N9 -0.5(3) . . . . ?
C29 N7 N8 N9 -179.8(2) . . . . ?
N7 N8 N9 C32 -0.1(3) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
C9 C1 C2 C3 -178.4(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C4 C5 C6 C7 179.2(3) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
C9 C1 C6 C5 178.2(2) . . . . ?
C2 C1 C6 C7 179.9(2) . . . . ?
C9 C1 C6 C7 -0.4(3) . . . . ?
N2 N1 C7 C6 177.2(2) . . . . ?
C9 N1 C7 C6 -0.2(3) . . . . ?
N2 N1 C7 C17 60.4(3) . . . . ?
C9 N1 C7 C17 -117.0(2) . . . . ?
N2 N1 C7 C8 -69.2(3) . . . . ?
C9 N1 C7 C8 113.4(2) . . . . ?
C5 C6 C7 N1 -178.1(3) . . . . ?
C1 C6 C7 N1 0.3(3) . . . . ?
C5 C6 C7 C17 -61.0(3) . . . . ?
C1 C6 C7 C17 117.4(2) . . . . ?
C5 C6 C7 C8 67.5(4) . . . . ?
C1 C6 C7 C8 -114.0(2) . . . . ?
N5 N4 C8 C7 172.7(2) . . . . ?
N1 C7 C8 N4 70.9(3) . . . . ?
C6 C7 C8 N4 176.9(2) . . . . ?
C17 C7 C8 N4 -56.7(3) . . . . ?
N2 N1 C9 C10 1.1(3) . . . . ?
C7 N1 C9 C10 179.0(2) . . . . ?
N2 N1 C9 C1 -177.8(2) . . . . ?
C7 N1 C9 C1 0.0(3) . . . . ?
C2 C1 C9 N1 179.9(3) . . . . ?
C6 C1 C9 N1 0.2(3) . . . . ?
C2 C1 C9 C10 1.9(7) . . . . ?
C6 C1 C9 C10 -177.7(4) . . . . ?
N2 N3 C10 C9 0.3(3) . . . . ?
N2 N3 C10 C11 178.1(2) . . . . ?
N1 C9 C10 N3 -0.8(3) . . . . ?
C1 C9 C10 N3 177.2(4) . . . . ?
N1 C9 C10 C11 -178.3(3) . . . . ?
C1 C9 C10 C11 -0.3(7) . . . . ?
N3 C10 C11 C12 -1.9(4) . . . . ?
C9 C10 C11 C12 175.3(3) . . . . ?
N3 C10 C11 C16 179.5(3) . . . . ?
C9 C10 C11 C16 -3.3(5) . . . . ?
C16 C11 C12 C13 2.3(5) . . . . ?
C10 C11 C12 C13 -176.4(3) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 -1.4(6) . . . . ?
C13 C14 C15 C16 1.2(6) . . . . ?
C14 C15 C16 C11 0.7(5) . . . . ?
C12 C11 C16 C15 -2.4(5) . . . . ?
C10 C11 C16 C15 176.2(3) . . . . ?
N1 C7 C17 C22 -148.9(3) . . . . ?
C6 C7 C17 C22 103.0(3) . . . . ?
C8 C7 C17 C22 -22.2(4) . . . . ?
N1 C7 C17 C18 34.2(3) . . . . ?
C6 C7 C17 C18 -73.8(3) . . . . ?
C8 C7 C17 C18 161.0(3) . . . . ?
C22 C17 C18 C19 -0.9(4) . . . . ?
C7 C17 C18 C19 176.0(3) . . . . ?
C17 C18 C19 C20 0.4(5) . . . . ?
C18 C19 C20 C21 0.5(5) . . . . ?
C19 C20 C21 C22 -0.9(5) . . . . ?
C20 C21 C22 C17 0.4(5) . . . . ?
C18 C17 C22 C21 0.5(5) . . . . ?
C7 C17 C22 C21 -176.4(3) . . . . ?
C28 C23 C24 C25 0.1(4) . . . . ?
C31 C23 C24 C25 178.6(3) . . . . ?
C23 C24 C25 C26 -1.1(5) . . . . ?
C24 C25 C26 C27 1.5(5) . . . . ?
C25 C26 C27 C28 -0.9(5) . . . . ?
C26 C27 C28 C23 -0.2(4) . . . . ?
C26 C27 C28 C29 179.7(3) . . . . ?
C24 C23 C28 C27 0.6(4) . . . . ?
C31 C23 C28 C27 -178.3(2) . . . . ?
C24 C23 C28 C29 -179.3(2) . . . . ?
C31 C23 C28 C29 1.8(3) . . . . ?
N8 N7 C29 C39 61.8(3) . . . . ?
C31 N7 C29 C39 -117.5(2) . . . . ?
N8 N7 C29 C28 -179.7(2) . . . . ?
C31 N7 C29 C28 1.0(3) . . . . ?
N8 N7 C29 C30 -66.1(3) . . . . ?
C31 N7 C29 C30 114.6(2) . . . . ?
C27 C28 C29 N7 178.4(3) . . . . ?
C23 C28 C29 N7 -1.7(3) . . . . ?
C27 C28 C29 C39 -63.6(4) . . . . ?
C23 C28 C29 C39 116.3(3) . . . . ?
C27 C28 C29 C30 64.5(3) . . . . ?
C23 C28 C29 C30 -115.6(3) . . . . ?
N11 N10 C30 C29 113.2(3) . . . . ?
N7 C29 C30 N10 68.8(3) . . . . ?
C39 C29 C30 N10 -57.6(3) . . . . ?
C28 C29 C30 N10 175.3(2) . . . . ?
N8 N7 C31 C32 0.8(3) . . . . ?
C29 N7 C31 C32 -179.8(2) . . . . ?
N8 N7 C31 C23 -179.5(2) . . . . ?
C29 N7 C31 C23 -0.1(3) . . . . ?
C24 C23 C31 N7 -179.7(3) . . . . ?
C28 C23 C31 N7 -1.1(3) . . . . ?
C24 C23 C31 C32 -0.3(7) . . . . ?
C28 C23 C31 C32 178.3(4) . . . . ?
N8 N9 C32 C31 0.6(3) . . . . ?
N8 N9 C32 C33 179.4(2) . . . . ?
N7 C31 C32 N9 -0.8(3) . . . . ?
C23 C31 C32 N9 179.7(4) . . . . ?
N7 C31 C32 C33 -179.5(3) . . . . ?
C23 C31 C32 C33 1.1(7) . . . . ?
N9 C32 C33 C38 177.0(3) . . . . ?
C31 C32 C33 C38 -4.5(5) . . . . ?
N9 C32 C33 C34 -3.0(4) . . . . ?
C31 C32 C33 C34 175.5(3) . . . . ?
C38 C33 C34 C35 1.2(5) . . . . ?
C32 C33 C34 C35 -178.8(3) . . . . ?
C33 C34 C35 C36 -1.0(5) . . . . ?
C34 C35 C36 C37 0.4(5) . . . . ?
C35 C36 C37 C38 0.0(5) . . . . ?
C34 C33 C38 C37 -0.9(5) . . . . ?
C32 C33 C38 C37 179.1(3) . . . . ?
C36 C37 C38 C33 0.3(5) . . . . ?
N7 C29 C39 C44 -159.8(2) . . . . ?
C28 C29 C39 C44 90.6(3) . . . . ?
C30 C29 C39 C44 -34.6(4) . . . . ?
N7 C29 C39 C40 22.8(3) . . . . ?
C28 C29 C39 C40 -86.9(3) . . . . ?
C30 C29 C39 C40 147.9(3) . . . . ?
C44 C39 C40 C41 -1.3(4) . . . . ?
C29 C39 C40 C41 176.2(3) . . . . ?
C39 C40 C41 C42 2.8(5) . . . . ?
C40 C41 C42 C43 -2.8(5) . . . . ?
C41 C42 C43 C44 1.2(5) . . . . ?
C42 C43 C44 C39 0.3(5) . . . . ?
C40 C39 C44 C43 -0.3(4) . . . . ?
C29 C39 C44 C43 -177.7(3) . . . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4

