# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cd16102
_database_code_depnum_ccdc_archive 'CCDC 1465122'
_audit_update_record             
;
2016-03-12 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 F N4'
_chemical_formula_weight         372.44

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      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                   10.5273(12)
_cell_length_b                   11.4221(14)
_cell_length_c                   34.217(4)
_cell_angle_alpha                90.072(3)
_cell_angle_beta                 98.137(3)
_cell_angle_gamma                105.697(3)
_cell_volume                     3917.7(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2571
_cell_measurement_theta_min      4.407
_cell_measurement_theta_max      44.168

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5346
_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            22738
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         0.602
_diffrn_reflns_theta_max         25.500
_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             14545
_reflns_number_gt                6773
_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)+(0.1139P)²] 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         14545
_refine_ls_number_parameters     1009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.2272
_refine_ls_wR_factor_gt          0.1742
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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 0.3477(2) 0.0432(2) -0.10437(7) 0.1081(8) Uani 1 1 d . . . . .
F2 F 0.3301(2) 0.54592(19) -0.09942(6) 0.0991(7) Uani 1 1 d . . . . .
F3 F 0.6725(2) 1.13119(19) 0.60021(6) 0.0956(7) Uani 1 1 d . . . . .
F4 F 0.6489(2) 0.6157(2) 0.60358(7) 0.1040(7) Uani 1 1 d . . . . .
N1 N 1.0070(2) 0.2842(2) 0.12374(7) 0.0486(6) Uani 1 1 d . . . . .
N2 N 0.9572(3) 0.2187(2) 0.05338(7) 0.0543(6) Uani 1 1 d . . . . .
N3 N 0.9801(3) 0.1107(3) 0.04916(9) 0.0740(8) Uani 1 1 d . . . . .
N4 N 0.8514(2) 0.2326(2) 0.02976(7) 0.0512(6) Uani 1 1 d . . . . .
N5 N 1.0015(2) 0.7840(2) 0.12394(7) 0.0481(6) Uani 1 1 d . . . . .
N6 N 0.9536(2) 0.7216(2) 0.05336(7) 0.0532(6) Uani 1 1 d . . . . .
N7 N 0.9825(3) 0.6173(2) 0.04697(8) 0.0640(7) Uani 1 1 d . . . . .
N8 N 0.8426(2) 0.7332(2) 0.03171(7) 0.0518(6) Uani 1 1 d . . . . .
N9 N 0.0015(2) 1.0349(2) 0.37553(7) 0.0507(6) Uani 1 1 d . . . . .
N10 N 0.0521(3) 0.9985(2) 0.44632(7) 0.0546(6) Uani 1 1 d . . . . .
N11 N 0.0214(3) 0.8811(2) 0.45372(9) 0.0703(8) Uani 1 1 d . . . . .
N12 N 0.1636(2) 1.0655(2) 0.46770(7) 0.0535(6) Uani 1 1 d . . . . .
N13 N -0.0082(2) 0.53265(19) 0.37647(6) 0.0451(6) Uani 1 1 d . . . . .
N14 N 0.0373(2) 0.4899(2) 0.44680(7) 0.0497(6) Uani 1 1 d . . . . .
N15 N 0.0148(3) 0.3703(2) 0.45013(8) 0.0634(7) Uani 1 1 d . . . . .
N16 N 0.1434(2) 0.5567(2) 0.47050(7) 0.0495(6) Uani 1 1 d . . . . .
C1 C 0.8826(4) 0.0535(3) 0.02097(11) 0.0735(10) Uani 1 1 d . . . . .
H1 H 0.8703 -0.0253 0.0111 0.088 Uiso 1 1 calc R U . . .
C2 C 0.8025(3) 0.1277(3) 0.00858(8) 0.0518(7) Uani 1 1 d . . . . .
C3 C 0.6848(3) 0.1053(3) -0.02176(8) 0.0542(8) Uani 1 1 d . . . . .
C4 C 0.6158(4) -0.0092(3) -0.03564(13) 0.1015(14) Uani 1 1 d . . . . .
H4 H 0.6448 -0.0750 -0.0259 0.122 Uiso 1 1 calc R U . . .
C5 C 0.5038(5) -0.0298(4) -0.06375(14) 0.1125(16) Uani 1 1 d . . . . .
H5 H 0.4590 -0.1087 -0.0731 0.135 Uiso 1 1 calc R U . . .
C6 C 0.4598(4) 0.0634(3) -0.07748(10) 0.0747(10) Uani 1 1 d . . . . .
C7 C 0.5298(4) 0.1773(3) -0.06644(11) 0.0950(13) Uani 1 1 d . . . . .
H7 H 0.5025 0.2425 -0.0775 0.114 Uiso 1 1 calc R U . . .
C8 C 0.6432(4) 0.1986(3) -0.03852(11) 0.0831(11) Uani 1 1 d . . . . .
H8 H 0.6918 0.2783 -0.0311 0.100 Uiso 1 1 calc R U . . .
C9 C 1.0343(3) 0.3104(3) 0.08430(8) 0.0545(8) Uani 1 1 d . . . . .
H9A H 1.1285 0.3197 0.0839 0.065 Uiso 1 1 calc R U . . .
H9B H 1.0171 0.3878 0.0777 0.065 Uiso 1 1 calc R U . . .
C10 C 0.8652(3) 0.2607(3) 0.12725(8) 0.0589(8) Uani 1 1 d . . . . .
H10A H 0.8169 0.1820 0.1147 0.071 Uiso 1 1 calc R U . . .
H10B H 0.8302 0.3220 0.1134 0.071 Uiso 1 1 calc R U . . .
C11 C 0.8418(3) 0.2623(3) 0.16960(8) 0.0507(7) Uani 1 1 d . . . . .
C12 C 0.8945(3) 0.3664(3) 0.19377(10) 0.0650(9) Uani 1 1 d . . . . .
H12 H 0.9460 0.4363 0.1838 0.078 Uiso 1 1 calc R U . . .
C13 C 0.8716(4) 0.3678(3) 0.23234(11) 0.0767(10) Uani 1 1 d . . . . .
H13 H 0.9071 0.4385 0.2482 0.092 Uiso 1 1 calc R U . . .
C14 C 0.7966(4) 0.2655(4) 0.24749(10) 0.0771(10) Uani 1 1 d . . . . .
H14 H 0.7804 0.2666 0.2735 0.092 Uiso 1 1 calc R U . . .
C15 C 0.7460(3) 0.1620(3) 0.22405(10) 0.0717(9) Uani 1 1 d . . . . .
H15 H 0.6961 0.0919 0.2343 0.086 Uiso 1 1 calc R U . . .
C16 C 0.7682(3) 0.1606(3) 0.18550(9) 0.0596(8) Uani 1 1 d . . . . .
H16 H 0.7327 0.0894 0.1699 0.072 Uiso 1 1 calc R U . . .
C17 C 1.0667(3) 0.1910(3) 0.14166(9) 0.0531(7) Uani 1 1 d . . . . .
H17A H 1.0449 0.1209 0.1234 0.064 Uiso 1 1 calc R U . . .
H17B H 1.0291 0.1648 0.1655 0.064 Uiso 1 1 calc R U . . .
C18 C 1.2161(3) 0.2382(3) 0.15169(8) 0.0512(7) Uani 1 1 d . . . . .
C19 C 1.2722(3) 0.3382(3) 0.17659(10) 0.0677(9) Uani 1 1 d . . . . .
H19 H 1.2176 0.3812 0.1855 0.081 Uiso 1 1 calc R U . . .
C20 C 1.4081(4) 0.3767(4) 0.18876(12) 0.0844(11) Uani 1 1 d . . . . .
H20 H 1.4437 0.4445 0.2059 0.101 Uiso 1 1 calc R U . . .
C21 C 1.4906(4) 0.3161(4) 0.17580(13) 0.0904(12) Uani 1 1 d . . . . .
H21 H 1.5821 0.3413 0.1842 0.108 Uiso 1 1 calc R U . . .
C22 C 1.4366(4) 0.2187(4) 0.15045(14) 0.1020(14) Uani 1 1 d . . . . .
H22 H 1.4921 0.1776 0.1411 0.122 Uiso 1 1 calc R U . . .
C23 C 1.3000(4) 0.1788(3) 0.13811(11) 0.0810(11) Uani 1 1 d . . . . .
H23 H 1.2651 0.1118 0.1206 0.097 Uiso 1 1 calc R U . . .
C24 C 0.8841(3) 0.5601(3) 0.01914(10) 0.0615(8) Uani 1 1 d . . . . .
H24 H 0.8754 0.4837 0.0078 0.074 Uiso 1 1 calc R U . . .
C25 C 0.7962(3) 0.6301(2) 0.00923(8) 0.0488(7) Uani 1 1 d . . . . .
C26 C 0.6740(3) 0.6083(2) -0.01945(8) 0.0493(7) Uani 1 1 d . . . . .
C27 C 0.6507(3) 0.5304(3) -0.05210(10) 0.0674(9) Uani 1 1 d . . . . .
H27 H 0.7145 0.4908 -0.0562 0.081 Uiso 1 1 calc R U . . .
C28 C 0.5347(4) 0.5095(3) -0.07892(11) 0.0792(11) Uani 1 1 d . . . . .
H28 H 0.5208 0.4569 -0.1008 0.095 Uiso 1 1 calc R U . . .
C29 C 0.4433(4) 0.5659(3) -0.07293(10) 0.0674(9) Uani 1 1 d . . . . .
C30 C 0.4574(4) 0.6429(3) -0.04084(11) 0.0786(10) Uani 1 1 d . . . . .
H30 H 0.3914 0.6801 -0.0371 0.094 Uiso 1 1 calc R U . . .
C31 C 0.5748(3) 0.6630(3) -0.01411(10) 0.0705(10) Uani 1 1 d . . . . .
H31 H 0.5870 0.7147 0.0080 0.085 Uiso 1 1 calc R U . . .
C32 C 1.0303(3) 0.8127(2) 0.08479(8) 0.0532(7) Uani 1 1 d . . . . .
H32A H 1.1246 0.8225 0.0845 0.064 Uiso 1 1 calc R U . . .
H32B H 1.0129 0.8903 0.0786 0.064 Uiso 1 1 calc R U . . .
C33 C 0.8594(3) 0.7620(3) 0.12739(8) 0.0580(8) Uani 1 1 d . . . . .
H33A H 0.8098 0.6847 0.1141 0.070 Uiso 1 1 calc R U . . .
H33B H 0.8261 0.8253 0.1143 0.070 Uiso 1 1 calc R U . . .
C34 C 0.8363(3) 0.7602(3) 0.16973(8) 0.0506(7) Uani 1 1 d . . . . .
C35 C 0.8855(3) 0.8633(3) 0.19471(10) 0.0638(9) Uani 1 1 d . . . . .
H35 H 0.9342 0.9352 0.1851 0.077 Uiso 1 1 calc R U . . .
C36 C 0.8635(3) 0.8610(3) 0.23316(11) 0.0720(10) Uani 1 1 d . . . . .
H36 H 0.8966 0.9315 0.2493 0.086 Uiso 1 1 calc R U . . .
C37 C 0.7934(3) 0.7563(3) 0.24833(10) 0.0706(10) Uani 1 1 d . . . . .
H37 H 0.7788 0.7554 0.2745 0.085 Uiso 1 1 calc R U . . .
C38 C 0.7447(3) 0.6522(3) 0.22435(10) 0.0651(9) Uani 1 1 d . . . . .
H38 H 0.6976 0.5803 0.2343 0.078 Uiso 1 1 calc R U . . .
C39 C 0.7663(3) 0.6551(3) 0.18537(9) 0.0580(8) Uani 1 1 d . . . . .
H39 H 0.7327 0.5846 0.1693 0.070 Uiso 1 1 calc R U . . .
C40 C 1.0607(3) 0.6911(2) 0.14164(9) 0.0520(7) Uani 1 1 d . . . . .
H40A H 1.0408 0.6222 0.1230 0.062 Uiso 1 1 calc R U . . .
H40B H 1.0207 0.6628 0.1650 0.062 Uiso 1 1 calc R U . . .
C41 C 1.2093(3) 0.7378(3) 0.15297(8) 0.0509(7) Uani 1 1 d . . . . .
C42 C 1.2672(3) 0.8528(3) 0.17015(11) 0.0727(10) Uani 1 1 d . . . . .
H42 H 1.2144 0.9051 0.1726 0.087 Uiso 1 1 calc R U . . .
C43 C 1.4015(4) 0.8911(4) 0.18369(12) 0.0882(12) Uani 1 1 d . . . . .
H43 H 1.4384 0.9691 0.1950 0.106 Uiso 1 1 calc R U . . .
C44 C 1.4815(4) 0.8165(4) 0.18082(12) 0.0882(12) Uani 1 1 d . . . . .
H44 H 1.5726 0.8432 0.1898 0.106 Uiso 1 1 calc R U . . .
C45 C 1.4251(4) 0.7017(4) 0.16446(11) 0.0916(13) Uani 1 1 d . . . . .
H45 H 1.4781 0.6491 0.1630 0.110 Uiso 1 1 calc R U . . .
C46 C 1.2902(4) 0.6627(3) 0.15008(10) 0.0731(10) Uani 1 1 d . . . . .
H46 H 1.2541 0.5851 0.1384 0.088 Uiso 1 1 calc R U . . .
C47 C 0.1186(3) 0.8728(3) 0.48147(10) 0.0652(9) Uani 1 1 d . . . . .
H47 H 0.1263 0.8011 0.4932 0.078 Uiso 1 1 calc R U . . .
C48 C 0.2081(3) 0.9867(3) 0.49068(8) 0.0496(7) Uani 1 1 d . . . . .
C49 C 0.3304(3) 1.0240(2) 0.51981(8) 0.0486(7) Uani 1 1 d . . . . .
C50 C 0.3493(3) 0.9581(3) 0.55293(9) 0.0615(9) Uani 1 1 d . . . . .
H50 H 0.2834 0.8882 0.5570 0.074 Uiso 1 1 calc R U . . .
C51 C 0.4639(4) 0.9940(3) 0.58002(10) 0.0684(9) Uani 1 1 d . . . . .
H51 H 0.4753 0.9493 0.6023 0.082 Uiso 1 1 calc R U . . .
C52 C 0.5598(4) 1.0954(3) 0.57367(10) 0.0653(9) Uani 1 1 d . . . . .
C53 C 0.5469(3) 1.1636(3) 0.54097(10) 0.0652(9) Uani 1 1 d . . . . .
H53 H 0.6142 1.2324 0.5370 0.078 Uiso 1 1 calc R U . . .
C54 C 0.4306(3) 1.1265(3) 0.51425(9) 0.0573(8) Uani 1 1 d . . . . .
H54 H 0.4197 1.1716 0.4920 0.069 Uiso 1 1 calc R U . . .
C55 C -0.0249(3) 1.0506(3) 0.41526(9) 0.0561(8) Uani 1 1 d . . . . .
H55A H -0.1190 1.0140 0.4160 0.067 Uiso 1 1 calc R U . . .
H55B H -0.0067 1.1370 0.4214 0.067 Uiso 1 1 calc R U . . .
C56 C 0.1427(3) 1.0834(3) 0.37154(9) 0.0598(8) Uani 1 1 d . . . . .
H56A H 0.1928 1.0311 0.3847 0.072 Uiso 1 1 calc R U . . .
H56B H 0.1766 1.1636 0.3845 0.072 Uiso 1 1 calc R U . . .
C57 C 0.1639(3) 1.0920(3) 0.32892(9) 0.0535(7) Uani 1 1 d . . . . .
C58 C 0.1129(3) 1.1691(3) 0.30424(10) 0.0652(9) Uani 1 1 d . . . . .
H58 H 0.0645 1.2166 0.3140 0.078 Uiso 1 1 calc R U . . .
C59 C 0.1330(4) 1.1764(3) 0.26525(11) 0.0762(10) Uani 1 1 d . . . . .
H59 H 0.0986 1.2291 0.2490 0.091 Uiso 1 1 calc R U . . .
C60 C 0.2035(3) 1.1062(3) 0.25040(10) 0.0715(9) Uani 1 1 d . . . . .
H60 H 0.2174 1.1113 0.2241 0.086 Uiso 1 1 calc R U . . .
C61 C 0.2531(3) 1.0287(3) 0.27446(10) 0.0670(9) Uani 1 1 d . . . . .
H61 H 0.3005 0.9805 0.2645 0.080 Uiso 1 1 calc R U . . .
C62 C 0.2332(3) 1.0215(3) 0.31347(9) 0.0587(8) Uani 1 1 d . . . . .
H62 H 0.2672 0.9682 0.3295 0.070 Uiso 1 1 calc R U . . .
C63 C -0.0580(3) 0.9108(2) 0.35887(9) 0.0544(8) Uani 1 1 d . . . . .
H63A H -0.0349 0.8537 0.3776 0.065 Uiso 1 1 calc R U . . .
H63B H -0.0211 0.9011 0.3350 0.065 Uiso 1 1 calc R U . . .
C64 C -0.2072(3) 0.8817(3) 0.34921(9) 0.0517(7) Uani 1 1 d . . . . .
C65 C -0.2649(3) 0.9530(3) 0.32423(10) 0.0657(9) Uani 1 1 d . . . . .
H65 H -0.2108 1.0229 0.3151 0.079 Uiso 1 1 calc R U . . .
C66 C -0.4010(4) 0.9237(4) 0.31235(11) 0.0826(11) Uani 1 1 d . . . . .
H66 H -0.4376 0.9727 0.2950 0.099 Uiso 1 1 calc R U . . .
C67 C -0.4819(4) 0.8219(4) 0.32619(14) 0.0907(13) Uani 1 1 d . . . . .
H67 H -0.5738 0.8014 0.3185 0.109 Uiso 1 1 calc R U . . .
C68 C -0.4261(4) 0.7515(4) 0.35133(14) 0.0963(13) Uani 1 1 d . . . . .
H68 H -0.4806 0.6824 0.3608 0.116 Uiso 1 1 calc R U . . .
C69 C -0.2895(4) 0.7809(3) 0.36313(11) 0.0777(10) Uani 1 1 d . . . . .
H69 H -0.2533 0.7320 0.3806 0.093 Uiso 1 1 calc R U . . .
C70 C 0.1126(3) 0.3608(3) 0.47802(10) 0.0632(9) Uani 1 1 d . . . . .
H70 H 0.1256 0.2879 0.4874 0.076 Uiso 1 1 calc R U . . .
C71 C 0.1925(3) 0.4754(2) 0.49114(8) 0.0477(7) Uani 1 1 d . . . . .
C72 C 0.3106(3) 0.5116(2) 0.52146(8) 0.0492(7) Uani 1 1 d . . . . .
C73 C 0.3810(4) 0.4303(3) 0.53410(11) 0.0791(11) Uani 1 1 d . . . . .
H73 H 0.3523 0.3507 0.5237 0.095 Uiso 1 1 calc R U . . .
C74 C 0.4942(4) 0.4649(4) 0.56206(11) 0.0913(12) Uani 1 1 d . . . . .
H74 H 0.5409 0.4088 0.5705 0.110 Uiso 1 1 calc R U . . .
C75 C 0.5365(4) 0.5810(3) 0.57706(10) 0.0704(9) Uani 1 1 d . . . . .
C76 C 0.4672(3) 0.6623(3) 0.56601(9) 0.0704(9) Uani 1 1 d . . . . .
H76 H 0.4953 0.7410 0.5771 0.085 Uiso 1 1 calc R U . . .
C77 C 0.3547(3) 0.6275(3) 0.53813(9) 0.0622(8) Uani 1 1 d . . . . .
H77 H 0.3075 0.6838 0.5304 0.075 Uiso 1 1 calc R U . . .
C78 C -0.0376(3) 0.5443(2) 0.41578(8) 0.0491(7) Uani 1 1 d . . . . .
H78A H -0.1321 0.5071 0.4157 0.059 Uiso 1 1 calc R U . . .
H78B H -0.0202 0.6302 0.4226 0.059 Uiso 1 1 calc R U . . .
C79 C 0.1345(3) 0.5799(3) 0.37365(8) 0.0554(8) Uani 1 1 d . . . . .
H79A H 0.1821 0.5251 0.3863 0.066 Uiso 1 1 calc R U . . .
H79B H 0.1689 0.6585 0.3877 0.066 Uiso 1 1 calc R U . . .
C80 C 0.1597(3) 0.5935(3) 0.33151(8) 0.0479(7) Uani 1 1 d . . . . .
C81 C 0.1081(3) 0.6718(3) 0.30705(10) 0.0632(8) Uani 1 1 d . . . . .
H81 H 0.0562 0.7159 0.3168 0.076 Uiso 1 1 calc R U . . .
C82 C 0.1324(3) 0.6850(3) 0.26872(10) 0.0712(9) Uani 1 1 d . . . . .
H82 H 0.0976 0.7382 0.2528 0.085 Uiso 1 1 calc R U . . .
C83 C 0.2074(3) 0.6204(3) 0.25390(10) 0.0729(10) Uani 1 1 d . . . . .
H83 H 0.2243 0.6296 0.2280 0.088 Uiso 1 1 calc R U . . .
C84 C 0.2577(3) 0.5419(3) 0.27739(10) 0.0698(9) Uani 1 1 d . . . . .
H84 H 0.3085 0.4973 0.2673 0.084 Uiso 1 1 calc R U . . .
C85 C 0.2339(3) 0.5286(3) 0.31570(9) 0.0593(8) Uani 1 1 d . . . . .
H85 H 0.2686 0.4746 0.3313 0.071 Uiso 1 1 calc R U . . .
C86 C -0.0679(3) 0.4109(2) 0.35784(8) 0.0505(7) Uani 1 1 d . . . . .
H86A H -0.0488 0.3508 0.3761 0.061 Uiso 1 1 calc R U . . .
H86B H -0.0272 0.4039 0.3345 0.061 Uiso 1 1 calc R U . . .
C87 C -0.2164(3) 0.3839(3) 0.34613(8) 0.0482(7) Uani 1 1 d . . . . .
C88 C -0.2733(3) 0.4699(3) 0.32936(11) 0.0718(10) Uani 1 1 d . . . . .
H88 H -0.2197 0.5485 0.3275 0.086 Uiso 1 1 calc R U . . .
C89 C -0.4074(4) 0.4432(4) 0.31518(12) 0.0869(12) Uani 1 1 d . . . . .
H89 H -0.4435 0.5031 0.3038 0.104 Uiso 1 1 calc R U . . .
C90 C -0.4873(4) 0.3275(4) 0.31801(12) 0.0862(12) Uani 1 1 d . . . . .
H90 H -0.5782 0.3084 0.3087 0.103 Uiso 1 1 calc R U . . .
C91 C -0.4319(4) 0.2410(4) 0.33460(11) 0.0844(12) Uani 1 1 d . . . . .
H91 H -0.4857 0.1623 0.3363 0.101 Uiso 1 1 calc R U . . .
C92 C -0.2976(3) 0.2681(3) 0.34897(9) 0.0661(9) Uani 1 1 d . . . . .
H92 H -0.2617 0.2083 0.3606 0.079 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 C6 1.356(4) . ?
F2 C29 1.357(4) . ?
F3 C52 1.353(4) . ?
F4 C75 1.350(4) . ?
N1 C9 1.435(3) . ?
N1 C10 1.466(3) . ?
N1 C17 1.469(3) . ?
N2 N4 1.327(3) . ?
N2 N3 1.330(3) . ?
N2 C9 1.473(3) . ?
N3 C1 1.328(4) . ?
N4 C2 1.335(3) . ?
N5 C32 1.434(3) . ?
N5 C40 1.461(3) . ?
N5 C33 1.470(3) . ?
N6 N8 1.331(3) . ?
N6 N7 1.332(3) . ?
N6 C32 1.479(3) . ?
N7 C24 1.326(4) . ?
N8 C25 1.340(3) . ?
N9 C55 1.445(4) . ?
N9 C63 1.464(3) . ?
N9 C56 1.466(3) . ?
N10 N11 1.325(3) . ?
N10 N12 1.330(3) . ?
N10 C55 1.469(4) . ?
N11 C47 1.318(4) . ?
N12 C48 1.332(3) . ?
N13 C78 1.436(3) . ?
N13 C86 1.465(3) . ?
N13 C79 1.470(3) . ?
N14 N15 1.329(3) . ?
N14 N16 1.330(3) . ?
N14 C78 1.471(4) . ?
N15 C70 1.329(4) . ?
N16 C71 1.337(3) . ?
C1 C2 1.377(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.463(4) . ?
C3 C8 1.356(4) . ?
C3 C4 1.361(4) . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.333(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.334(4) . ?
C7 C8 1.384(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.505(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.371(4) . ?
C11 C12 1.384(4) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.507(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.367(4) . ?
C18 C23 1.377(4) . ?
C19 C20 1.380(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.366(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.353(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.386(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.466(4) . ?
C26 C27 1.379(4) . ?
C26 C31 1.386(4) . ?
C27 C28 1.384(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.331(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.372(4) . ?
C30 C31 1.394(4) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.502(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C39 1.380(4) . ?
C34 C35 1.389(4) . ?
C35 C36 1.367(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.370(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.377(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.383(4) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 C41 1.503(4) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C46 1.375(4) . ?
C41 C42 1.381(4) . ?
C42 C43 1.372(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.362(5) . ?
C43 H43 0.9300 . ?
C44 C45 1.367(5) . ?
C44 H44 0.9300 . ?
C45 C46 1.384(5) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 C48 1.390(4) . ?
C47 H47 0.9300 . ?
C48 C49 1.474(4) . ?
C49 C54 1.381(4) . ?
C49 C50 1.382(4) . ?
C50 C51 1.378(4) . ?
C50 H50 0.9300 . ?
C51 C52 1.355(5) . ?
C51 H51 0.9300 . ?
C52 C53 1.377(4) . ?
C53 C54 1.384(4) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
C55 H55A 0.9700 . ?
C55 H55B 0.9700 . ?
C56 C57 1.506(4) . ?
C56 H56A 0.9700 . ?
C56 H56B 0.9700 . ?
C57 C62 1.373(4) . ?
C57 C58 1.381(4) . ?
C58 C59 1.379(5) . ?
C58 H58 0.9300 . ?
C59 C60 1.371(5) . ?
C59 H59 0.9300 . ?
C60 C61 1.365(4) . ?
C60 H60 0.9300 . ?
C61 C62 1.379(4) . ?
C61 H61 0.9300 . ?
C62 H62 0.9300 . ?
C63 C64 1.503(4) . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C64 C69 1.372(4) . ?
C64 C65 1.373(4) . ?
C65 C66 1.380(4) . ?
C65 H65 0.9300 . ?
C66 C67 1.372(5) . ?
C66 H66 0.9300 . ?
C67 C68 1.359(6) . ?
C67 H67 0.9300 . ?
C68 C69 1.385(5) . ?
C68 H68 0.9300 . ?
C69 H69 0.9300 . ?
C70 C71 1.385(4) . ?
C70 H70 0.9300 . ?
C71 C72 1.465(4) . ?
C72 C77 1.373(4) . ?
C72 C73 1.372(4) . ?
C73 C74 1.383(5) . ?
C73 H73 0.9300 . ?
C74 C75 1.354(5) . ?
C74 H74 0.9300 . ?
C75 C76 1.352(4) . ?
C76 C77 1.377(4) . ?
C76 H76 0.9300 . ?
C77 H77 0.9300 . ?
C78 H78A 0.9700 . ?
C78 H78B 0.9700 . ?
C79 C80 1.503(4) . ?
C79 H79A 0.9700 . ?
C79 H79B 0.9700 . ?
C80 C85 1.373(4) . ?
C80 C81 1.390(4) . ?
C81 C82 1.372(4) . ?
C81 H81 0.9300 . ?
C82 C83 1.361(5) . ?
C82 H82 0.9300 . ?
C83 C84 1.366(5) . ?
C83 H83 0.9300 . ?
C84 C85 1.370(4) . ?
C84 H84 0.9300 . ?
C85 H85 0.9300 . ?
C86 C87 1.504(4) . ?
C86 H86A 0.9700 . ?
C86 H86B 0.9700 . ?
C87 C88 1.369(4) . ?
C87 C92 1.379(4) . ?
C88 C89 1.376(4) . ?
C88 H88 0.9300 . ?
C89 C90 1.373(5) . ?
C89 H89 0.9300 . ?
C90 C91 1.363(5) . ?
C90 H90 0.9300 . ?
C91 C92 1.380(5) . ?
C91 H91 0.9300 . ?
C92 H92 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
C9 N1 C10 112.9(2) . . ?
C9 N1 C17 113.5(2) . . ?
C10 N1 C17 113.1(2) . . ?
N4 N2 N3 114.3(2) . . ?
N4 N2 C9 122.6(2) . . ?
N3 N2 C9 122.9(3) . . ?
C1 N3 N2 103.4(3) . . ?
N2 N4 C2 104.9(2) . . ?
C32 N5 C40 113.9(2) . . ?
C32 N5 C33 113.2(2) . . ?
C40 N5 C33 113.7(2) . . ?
N8 N6 N7 114.8(2) . . ?
N8 N6 C32 121.9(2) . . ?
N7 N6 C32 123.0(2) . . ?
C24 N7 N6 103.0(2) . . ?
N6 N8 C25 104.6(2) . . ?
C55 N9 C63 113.1(2) . . ?
C55 N9 C56 112.8(2) . . ?
C63 N9 C56 113.8(2) . . ?
N11 N10 N12 114.7(3) . . ?
N11 N10 C55 123.3(3) . . ?
N12 N10 C55 121.9(2) . . ?
C47 N11 N10 103.5(3) . . ?
N10 N12 C48 104.6(2) . . ?
C78 N13 C86 113.8(2) . . ?
C78 N13 C79 112.9(2) . . ?
C86 N13 C79 113.2(2) . . ?
N15 N14 N16 114.8(2) . . ?
N15 N14 C78 122.8(2) . . ?
N16 N14 C78 121.9(2) . . ?
C70 N15 N14 103.2(2) . . ?
N14 N16 C71 104.5(2) . . ?
N3 C1 C2 110.1(3) . . ?
N3 C1 H1 124.9 . . ?
C2 C1 H1 124.9 . . ?
N4 C2 C1 107.3(3) . . ?
N4 C2 C3 122.7(3) . . ?
C1 C2 C3 130.1(3) . . ?
C8 C3 C4 117.0(3) . . ?
C8 C3 C2 121.2(3) . . ?
C4 C3 C2 121.7(3) . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 120.0(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.1(4) . . ?
C5 C6 F1 120.1(3) . . ?
C7 C6 F1 119.7(4) . . ?
C6 C7 C8 120.0(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C3 C8 C7 121.2(3) . . ?
C3 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
N1 C9 N2 115.6(2) . . ?
N1 C9 H9A 108.4 . . ?
N2 C9 H9A 108.4 . . ?
N1 C9 H9B 108.4 . . ?
N2 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
N1 C10 C11 112.3(2) . . ?
N1 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C16 C11 C12 117.9(3) . . ?
C16 C11 C10 121.0(3) . . ?
C12 C11 C10 121.0(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N1 C17 C18 111.7(2) . . ?
N1 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
N1 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C23 117.9(3) . . ?
C19 C18 C17 120.5(3) . . ?
C23 C18 C17 121.5(3) . . ?
C18 C19 C20 121.3(3) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 120.5(4) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 118.7(4) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C22 C23 121.3(4) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C18 C23 C22 120.2(3) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
N7 C24 C25 110.6(3) . . ?
N7 C24 H24 124.7 . . ?
C25 C24 H24 124.7 . . ?
N8 C25 C24 107.0(3) . . ?
N8 C25 C26 121.4(3) . . ?
C24 C25 C26 131.7(3) . . ?
C27 C26 C31 117.1(3) . . ?
C27 C26 C25 121.9(3) . . ?
C31 C26 C25 121.0(3) . . ?
C26 C27 C28 121.6(3) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C29 C28 C27 119.1(3) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C28 C29 F2 119.0(3) . . ?
C28 C29 C30 123.0(3) . . ?
F2 C29 C30 118.0(3) . . ?
C29 C30 C31 117.2(3) . . ?
C29 C30 H30 121.4 . . ?
C31 C30 H30 121.4 . . ?
C26 C31 C30 121.9(3) . . ?
C26 C31 H31 119.0 . . ?
C30 C31 H31 119.0 . . ?
N5 C32 N6 115.2(2) . . ?
N5 C32 H32A 108.5 . . ?
N6 C32 H32A 108.5 . . ?
N5 C32 H32B 108.5 . . ?
N6 C32 H32B 108.5 . . ?
H32A C32 H32B 107.5 . . ?
N5 C33 C34 112.0(2) . . ?
N5 C33 H33A 109.2 . . ?
C34 C33 H33A 109.2 . . ?
N5 C33 H33B 109.2 . . ?
C34 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C39 C34 C35 117.5(3) . . ?
C39 C34 C33 121.0(3) . . ?
C35 C34 C33 121.5(3) . . ?
C36 C35 C34 121.1(3) . . ?
C36 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C35 C36 C37 120.9(3) . . ?
C35 C36 H36 119.6 . . ?
C37 C36 H36 119.6 . . ?
C36 C37 C38 119.3(3) . . ?
C36 C37 H37 120.4 . . ?
C38 C37 H37 120.4 . . ?
C37 C38 C39 119.7(3) . . ?
C37 C38 H38 120.2 . . ?
C39 C38 H38 120.2 . . ?
C34 C39 C38 121.6(3) . . ?
C34 C39 H39 119.2 . . ?
C38 C39 H39 119.2 . . ?
N5 C40 C41 112.4(2) . . ?
N5 C40 H40A 109.1 . . ?
C41 C40 H40A 109.1 . . ?
N5 C40 H40B 109.1 . . ?
C41 C40 H40B 109.1 . . ?
H40A C40 H40B 107.9 . . ?
C46 C41 C42 117.9(3) . . ?
C46 C41 C40 120.6(3) . . ?
C42 C41 C40 121.2(3) . . ?
C43 C42 C41 121.0(3) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C44 C43 C42 121.0(4) . . ?
C44 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C43 C44 C45 118.6(4) . . ?
C43 C44 H44 120.7 . . ?
C45 C44 H44 120.7 . . ?
C44 C45 C46 121.0(4) . . ?
C44 C45 H45 119.5 . . ?
C46 C45 H45 119.5 . . ?
C41 C46 C45 120.5(3) . . ?
C41 C46 H46 119.7 . . ?
C45 C46 H46 119.7 . . ?
N11 C47 C48 110.1(3) . . ?
N11 C47 H47 124.9 . . ?
C48 C47 H47 124.9 . . ?
N12 C48 C47 107.1(3) . . ?
N12 C48 C49 122.5(3) . . ?
C47 C48 C49 130.4(3) . . ?
C54 C49 C50 118.2(3) . . ?
C54 C49 C48 120.2(3) . . ?
C50 C49 C48 121.7(3) . . ?
C51 C50 C49 121.2(3) . . ?
C51 C50 H50 119.4 . . ?
C49 C50 H50 119.4 . . ?
C52 C51 C50 119.0(3) . . ?
C52 C51 H51 120.5 . . ?
C50 C51 H51 120.5 . . ?
F3 C52 C51 119.3(3) . . ?
F3 C52 C53 118.5(3) . . ?
C51 C52 C53 122.3(3) . . ?
C52 C53 C54 117.8(3) . . ?
C52 C53 H53 121.1 . . ?
C54 C53 H53 121.1 . . ?
C49 C54 C53 121.5(3) . . ?
C49 C54 H54 119.2 . . ?
C53 C54 H54 119.2 . . ?
N9 C55 N10 115.6(2) . . ?
N9 C55 H55A 108.4 . . ?
N10 C55 H55A 108.4 . . ?
N9 C55 H55B 108.4 . . ?
N10 C55 H55B 108.4 . . ?
H55A C55 H55B 107.5 . . ?
N9 C56 C57 111.9(2) . . ?
N9 C56 H56A 109.2 . . ?
C57 C56 H56A 109.2 . . ?
N9 C56 H56B 109.2 . . ?
C57 C56 H56B 109.2 . . ?
H56A C56 H56B 107.9 . . ?
C62 C57 C58 118.3(3) . . ?
C62 C57 C56 120.5(3) . . ?
C58 C57 C56 121.2(3) . . ?
C59 C58 C57 120.7(3) . . ?
C59 C58 H58 119.6 . . ?
C57 C58 H58 119.6 . . ?
C60 C59 C58 120.2(3) . . ?
C60 C59 H59 119.9 . . ?
C58 C59 H59 119.9 . . ?
C61 C60 C59 119.5(3) . . ?
C61 C60 H60 120.3 . . ?
C59 C60 H60 120.3 . . ?
C60 C61 C62 120.3(3) . . ?
C60 C61 H61 119.8 . . ?
C62 C61 H61 119.8 . . ?
C57 C62 C61 121.0(3) . . ?
C57 C62 H62 119.5 . . ?
C61 C62 H62 119.5 . . ?
N9 C63 C64 112.1(2) . . ?
N9 C63 H63A 109.2 . . ?
C64 C63 H63A 109.2 . . ?
N9 C63 H63B 109.2 . . ?
C64 C63 H63B 109.2 . . ?
H63A C63 H63B 107.9 . . ?
C69 C64 C65 118.0(3) . . ?
C69 C64 C63 121.7(3) . . ?
C65 C64 C63 120.2(3) . . ?
C64 C65 C66 121.8(3) . . ?
C64 C65 H65 119.1 . . ?
C66 C65 H65 119.1 . . ?
C67 C66 C65 119.6(4) . . ?
C67 C66 H66 120.2 . . ?
C65 C66 H66 120.2 . . ?
C68 C67 C66 119.1(4) . . ?
C68 C67 H67 120.4 . . ?
C66 C67 H67 120.4 . . ?
C67 C68 C69 121.1(4) . . ?
C67 C68 H68 119.4 . . ?
C69 C68 H68 119.4 . . ?
C64 C69 C68 120.3(4) . . ?
C64 C69 H69 119.8 . . ?
C68 C69 H69 119.8 . . ?
N15 C70 C71 110.1(3) . . ?
N15 C70 H70 125.0 . . ?
C71 C70 H70 125.0 . . ?
N16 C71 C70 107.4(3) . . ?
N16 C71 C72 122.3(3) . . ?
C70 C71 C72 130.3(3) . . ?
C77 C72 C73 117.7(3) . . ?
C77 C72 C71 121.4(3) . . ?
C73 C72 C71 120.9(3) . . ?
C72 C73 C74 121.0(3) . . ?
C72 C73 H73 119.5 . . ?
C74 C73 H73 119.5 . . ?
C75 C74 C73 119.5(3) . . ?
C75 C74 H74 120.3 . . ?
C73 C74 H74 120.3 . . ?
F4 C75 C76 119.6(3) . . ?
F4 C75 C74 119.6(3) . . ?
C76 C75 C74 120.9(3) . . ?
C75 C76 C77 119.4(3) . . ?
C75 C76 H76 120.3 . . ?
C77 C76 H76 120.3 . . ?
C72 C77 C76 121.4(3) . . ?
C72 C77 H77 119.3 . . ?
C76 C77 H77 119.3 . . ?
N13 C78 N14 115.7(2) . . ?
N13 C78 H78A 108.3 . . ?
N14 C78 H78A 108.3 . . ?
N13 C78 H78B 108.3 . . ?
N14 C78 H78B 108.3 . . ?
H78A C78 H78B 107.4 . . ?
N13 C79 C80 112.1(2) . . ?
N13 C79 H79A 109.2 . . ?
C80 C79 H79A 109.2 . . ?
N13 C79 H79B 109.2 . . ?
C80 C79 H79B 109.2 . . ?
H79A C79 H79B 107.9 . . ?
C85 C80 C81 117.5(3) . . ?
C85 C80 C79 121.3(3) . . ?
C81 C80 C79 121.2(3) . . ?
C82 C81 C80 121.1(3) . . ?
C82 C81 H81 119.4 . . ?
C80 C81 H81 119.4 . . ?
C83 C82 C81 120.2(3) . . ?
C83 C82 H82 119.9 . . ?
C81 C82 H82 119.9 . . ?
C82 C83 C84 119.5(3) . . ?
C82 C83 H83 120.2 . . ?
C84 C83 H83 120.2 . . ?
C83 C84 C85 120.5(3) . . ?
C83 C84 H84 119.7 . . ?
C85 C84 H84 119.7 . . ?
C84 C85 C80 121.1(3) . . ?
C84 C85 H85 119.4 . . ?
C80 C85 H85 119.4 . . ?
N13 C86 C87 112.6(2) . . ?
N13 C86 H86A 109.1 . . ?
C87 C86 H86A 109.1 . . ?
N13 C86 H86B 109.1 . . ?
C87 C86 H86B 109.1 . . ?
H86A C86 H86B 107.8 . . ?
C88 C87 C92 118.2(3) . . ?
C88 C87 C86 121.3(3) . . ?
C92 C87 C86 120.3(3) . . ?
C87 C88 C89 121.9(3) . . ?
C87 C88 H88 119.1 . . ?
C89 C88 H88 119.1 . . ?
C90 C89 C88 119.5(4) . . ?
C90 C89 H89 120.3 . . ?
C88 C89 H89 120.3 . . ?
C91 C90 C89 119.3(4) . . ?
C91 C90 H90 120.4 . . ?
C89 C90 H90 120.4 . . ?
C90 C91 C92 121.1(3) . . ?
C90 C91 H91 119.4 . . ?
C92 C91 H91 119.4 . . ?
C87 C92 C91 120.0(3) . . ?
C87 C92 H92 120.0 . . ?
C91 C92 H92 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 N2 N3 C1 0.2(3) . . . . ?
C9 N2 N3 C1 174.4(3) . . . . ?
N3 N2 N4 C2 -0.5(3) . . . . ?
C9 N2 N4 C2 -174.7(2) . . . . ?
N8 N6 N7 C24 0.8(3) . . . . ?
C32 N6 N7 C24 174.8(3) . . . . ?
N7 N6 N8 C25 -0.7(3) . . . . ?
C32 N6 N8 C25 -174.9(2) . . . . ?
N12 N10 N11 C47 0.2(3) . . . . ?
C55 N10 N11 C47 176.3(3) . . . . ?
N11 N10 N12 C48 -0.3(3) . . . . ?
C55 N10 N12 C48 -176.5(2) . . . . ?
N16 N14 N15 C70 0.4(3) . . . . ?
C78 N14 N15 C70 172.6(2) . . . . ?
N15 N14 N16 C71 -0.9(3) . . . . ?
C78 N14 N16 C71 -173.1(2) . . . . ?
N2 N3 C1 C2 0.1(4) . . . . ?
N2 N4 C2 C1 0.5(3) . . . . ?
N2 N4 C2 C3 -179.3(2) . . . . ?
N3 C1 C2 N4 -0.3(4) . . . . ?
N3 C1 C2 C3 179.4(3) . . . . ?
N4 C2 C3 C8 20.5(5) . . . . ?
C1 C2 C3 C8 -159.2(3) . . . . ?
N4 C2 C3 C4 -162.4(3) . . . . ?
C1 C2 C3 C4 17.9(5) . . . . ?
C8 C3 C4 C5 -3.8(6) . . . . ?
C2 C3 C4 C5 179.0(4) . . . . ?
C3 C4 C5 C6 -1.0(7) . . . . ?
C4 C5 C6 C7 5.4(7) . . . . ?
C4 C5 C6 F1 -178.3(4) . . . . ?
C5 C6 C7 C8 -4.6(6) . . . . ?
F1 C6 C7 C8 179.0(4) . . . . ?
C4 C3 C8 C7 4.6(6) . . . . ?
C2 C3 C8 C7 -178.2(3) . . . . ?
C6 C7 C8 C3 -0.4(6) . . . . ?
C10 N1 C9 N2 -54.6(3) . . . . ?
C17 N1 C9 N2 75.9(3) . . . . ?
N4 N2 C9 N1 100.9(3) . . . . ?
N3 N2 C9 N1 -72.8(3) . . . . ?
C9 N1 C10 C11 -166.7(2) . . . . ?
C17 N1 C10 C11 62.7(3) . . . . ?
N1 C10 C11 C16 -117.8(3) . . . . ?
N1 C10 C11 C12 61.9(4) . . . . ?
C16 C11 C12 C13 -1.0(5) . . . . ?
C10 C11 C12 C13 179.3(3) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
C12 C13 C14 C15 0.6(6) . . . . ?
C13 C14 C15 C16 -0.9(6) . . . . ?
C14 C15 C16 C11 0.3(5) . . . . ?
C12 C11 C16 C15 0.7(5) . . . . ?
C10 C11 C16 C15 -179.6(3) . . . . ?
C9 N1 C17 C18 71.4(3) . . . . ?
C10 N1 C17 C18 -158.2(2) . . . . ?
N1 C17 C18 C19 58.1(4) . . . . ?
N1 C17 C18 C23 -125.7(3) . . . . ?
C23 C18 C19 C20 -1.9(5) . . . . ?
C17 C18 C19 C20 174.5(3) . . . . ?
C18 C19 C20 C21 0.7(6) . . . . ?
C19 C20 C21 C22 0.8(6) . . . . ?
C20 C21 C22 C23 -1.1(7) . . . . ?
C19 C18 C23 C22 1.6(5) . . . . ?
C17 C18 C23 C22 -174.7(3) . . . . ?
C21 C22 C23 C18 -0.2(7) . . . . ?
N6 N7 C24 C25 -0.5(3) . . . . ?
N6 N8 C25 C24 0.4(3) . . . . ?
N6 N8 C25 C26 -179.3(2) . . . . ?
N7 C24 C25 N8 0.0(3) . . . . ?
N7 C24 C25 C26 179.7(3) . . . . ?
N8 C25 C26 C27 155.2(3) . . . . ?
C24 C25 C26 C27 -24.4(5) . . . . ?
N8 C25 C26 C31 -26.8(4) . . . . ?
C24 C25 C26 C31 153.6(3) . . . . ?
C31 C26 C27 C28 1.4(5) . . . . ?
C25 C26 C27 C28 179.5(3) . . . . ?
C26 C27 C28 C29 -0.3(5) . . . . ?
C27 C28 C29 F2 179.6(3) . . . . ?
C27 C28 C29 C30 -1.1(6) . . . . ?
C28 C29 C30 C31 1.1(6) . . . . ?
F2 C29 C30 C31 -179.5(3) . . . . ?
C27 C26 C31 C30 -1.4(5) . . . . ?
C25 C26 C31 C30 -179.5(3) . . . . ?
C29 C30 C31 C26 0.2(5) . . . . ?
C40 N5 C32 N6 76.1(3) . . . . ?
C33 N5 C32 N6 -55.8(3) . . . . ?
N8 N6 C32 N5 96.1(3) . . . . ?
N7 N6 C32 N5 -77.5(3) . . . . ?
C32 N5 C33 C34 -167.1(2) . . . . ?
C40 N5 C33 C34 60.9(3) . . . . ?
N5 C33 C34 C39 -114.4(3) . . . . ?
N5 C33 C34 C35 64.9(4) . . . . ?
C39 C34 C35 C36 -0.9(5) . . . . ?
C33 C34 C35 C36 179.7(3) . . . . ?
C34 C35 C36 C37 0.7(5) . . . . ?
C35 C36 C37 C38 0.1(5) . . . . ?
C36 C37 C38 C39 -0.6(5) . . . . ?
C35 C34 C39 C38 0.4(4) . . . . ?
C33 C34 C39 C38 179.8(3) . . . . ?
C37 C38 C39 C34 0.3(5) . . . . ?
C32 N5 C40 C41 72.1(3) . . . . ?
C33 N5 C40 C41 -156.2(2) . . . . ?
N5 C40 C41 C46 -145.5(3) . . . . ?
N5 C40 C41 C42 40.9(4) . . . . ?
C46 C41 C42 C43 0.4(5) . . . . ?
C40 C41 C42 C43 174.1(3) . . . . ?
C41 C42 C43 C44 -0.4(6) . . . . ?
C42 C43 C44 C45 -0.6(6) . . . . ?
C43 C44 C45 C46 1.8(6) . . . . ?
C42 C41 C46 C45 0.7(5) . . . . ?
C40 C41 C46 C45 -173.0(3) . . . . ?
C44 C45 C46 C41 -1.8(6) . . . . ?
N10 N11 C47 C48 0.1(3) . . . . ?
N10 N12 C48 C47 0.3(3) . . . . ?
N10 N12 C48 C49 -179.1(2) . . . . ?
N11 C47 C48 N12 -0.3(4) . . . . ?
N11 C47 C48 C49 179.1(3) . . . . ?
N12 C48 C49 C54 -26.3(4) . . . . ?
C47 C48 C49 C54 154.4(3) . . . . ?
N12 C48 C49 C50 154.4(3) . . . . ?
C47 C48 C49 C50 -24.9(5) . . . . ?
C54 C49 C50 C51 0.8(4) . . . . ?
C48 C49 C50 C51 -179.8(3) . . . . ?
C49 C50 C51 C52 -0.5(5) . . . . ?
C50 C51 C52 F3 179.9(3) . . . . ?
C50 C51 C52 C53 -0.3(5) . . . . ?
F3 C52 C53 C54 -179.4(3) . . . . ?
C51 C52 C53 C54 0.7(5) . . . . ?
C50 C49 C54 C53 -0.4(4) . . . . ?
C48 C49 C54 C53 -179.7(3) . . . . ?
C52 C53 C54 C49 -0.4(4) . . . . ?
C63 N9 C55 N10 74.9(3) . . . . ?
C56 N9 C55 N10 -56.1(3) . . . . ?
N11 N10 C55 N9 -79.2(4) . . . . ?
N12 N10 C55 N9 96.6(3) . . . . ?
C55 N9 C56 C57 -167.2(2) . . . . ?
C63 N9 C56 C57 62.2(3) . . . . ?
N9 C56 C57 C62 -114.6(3) . . . . ?
N9 C56 C57 C58 64.5(4) . . . . ?
C62 C57 C58 C59 -1.0(5) . . . . ?
C56 C57 C58 C59 179.9(3) . . . . ?
C57 C58 C59 C60 0.4(5) . . . . ?
C58 C59 C60 C61 0.3(5) . . . . ?
C59 C60 C61 C62 -0.4(5) . . . . ?
C58 C57 C62 C61 0.9(4) . . . . ?
C56 C57 C62 C61 180.0(3) . . . . ?
C60 C61 C62 C57 -0.2(5) . . . . ?
C55 N9 C63 C64 71.5(3) . . . . ?
C56 N9 C63 C64 -158.1(2) . . . . ?
N9 C63 C64 C69 -126.9(3) . . . . ?
N9 C63 C64 C65 56.5(4) . . . . ?
C69 C64 C65 C66 -1.7(5) . . . . ?
C63 C64 C65 C66 175.0(3) . . . . ?
C64 C65 C66 C67 1.1(5) . . . . ?
C65 C66 C67 C68 -0.2(6) . . . . ?
C66 C67 C68 C69 0.0(6) . . . . ?
C65 C64 C69 C68 1.5(5) . . . . ?
C63 C64 C69 C68 -175.2(3) . . . . ?
C67 C68 C69 C64 -0.7(6) . . . . ?
N14 N15 C70 C71 0.2(3) . . . . ?
N14 N16 C71 C70 0.9(3) . . . . ?
N14 N16 C71 C72 -179.2(2) . . . . ?
N15 C70 C71 N16 -0.7(3) . . . . ?
N15 C70 C71 C72 179.4(3) . . . . ?
N16 C71 C72 C77 18.6(4) . . . . ?
C70 C71 C72 C77 -161.6(3) . . . . ?
N16 C71 C72 C73 -161.3(3) . . . . ?
C70 C71 C72 C73 18.6(5) . . . . ?
C77 C72 C73 C74 -1.3(5) . . . . ?
C71 C72 C73 C74 178.5(3) . . . . ?
C72 C73 C74 C75 -0.3(6) . . . . ?
C73 C74 C75 F4 -178.2(3) . . . . ?
C73 C74 C75 C76 2.1(6) . . . . ?
F4 C75 C76 C77 178.2(3) . . . . ?
C74 C75 C76 C77 -2.2(6) . . . . ?
C73 C72 C77 C76 1.3(5) . . . . ?
C71 C72 C77 C76 -178.6(3) . . . . ?
C75 C76 C77 C72 0.5(5) . . . . ?
C86 N13 C78 N14 76.1(3) . . . . ?
C79 N13 C78 N14 -54.8(3) . . . . ?
N15 N14 C78 N13 -71.6(3) . . . . ?
N16 N14 C78 N13 100.0(3) . . . . ?
C78 N13 C79 C80 -167.0(2) . . . . ?
C86 N13 C79 C80 61.9(3) . . . . ?
N13 C79 C80 C85 -117.7(3) . . . . ?
N13 C79 C80 C81 61.9(4) . . . . ?
C85 C80 C81 C82 -1.1(4) . . . . ?
C79 C80 C81 C82 179.3(3) . . . . ?
C80 C81 C82 C83 0.5(5) . . . . ?
C81 C82 C83 C84 0.3(5) . . . . ?
C82 C83 C84 C85 -0.4(5) . . . . ?
C83 C84 C85 C80 -0.2(5) . . . . ?
C81 C80 C85 C84 1.0(4) . . . . ?
C79 C80 C85 C84 -179.4(3) . . . . ?
C78 N13 C86 C87 72.5(3) . . . . ?
C79 N13 C86 C87 -156.8(2) . . . . ?
N13 C86 C87 C88 41.4(4) . . . . ?
N13 C86 C87 C92 -144.2(3) . . . . ?
C92 C87 C88 C89 -0.6(5) . . . . ?
C86 C87 C88 C89 173.9(3) . . . . ?
C87 C88 C89 C90 0.3(6) . . . . ?
C88 C89 C90 C91 -0.4(6) . . . . ?
C89 C90 C91 C92 0.8(6) . . . . ?
C88 C87 C92 C91 0.9(5) . . . . ?
C86 C87 C92 C91 -173.6(3) . . . . ?
C90 C91 C92 C87 -1.0(5) . . . . ?

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
C10 H10B F2 0.97 2.55 3.452(4) 154.7 2_665
C17 H17A N3 0.97 2.53 3.227(4) 128.7 .
C40 H40A N7 0.97 2.58 3.278(4) 128.6 .
C56 H56A F3 0.97 2.63 3.575(4) 163.9 2_676
C63 H63A N11 0.97 2.59 3.277(4) 128.3 .
C79 H79B F3 0.97 2.52 3.416(3) 153.1 2_676
C86 H86A N15 0.97 2.52 3.223(4) 129.1 .

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4



