# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_db01
_audit_block_doi                 10.5517/cc11yxtq
_database_code_depnum_ccdc_archive 'CCDC 982074'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5CC09741J 2016
_audit_update_record             
;
2014-01-17 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 F N2'
_chemical_formula_weight         214.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0641(3)
_cell_length_b                   11.0425(3)
_cell_length_c                   12.1824(3)
_cell_angle_alpha                114.9240(10)
_cell_angle_beta                 95.0550(10)
_cell_angle_gamma                111.4760(10)
_cell_volume                     1094.39(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.49

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16663
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3848
_reflns_number_gt                3579
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0334P)²+0.4980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.043(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3848
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_iucr_refine_instruction_details 
;
TITL   DB01 in P-1
CELL 0.71073 10.0641 11.0425 12.1824 114.924 95.055 111.476
ZERR 4.00 0.0003 0.0003 0.0003 0.001 0.001 0.001
LATT  1
SFAC    C   H   N   F
UNIT    52  44  8  4
MERG    2
L.S.    12
OMIT -1 50
ACTA
BOND $H
HTAB
CONF
SIZE 0.3 0.25 0.1
TEMP -173
EXYZ C7A C7B
EXYZ C8A C12B
EXYZ C9A C11B
EXYZ C10A C10B
EXYZ C11A C9B
EXYZ C12A C8B
EADP F1A F1B
EADP C7A C7B
EADP C8A C12B
EADP C9A C11B
EADP C10A C10B
EADP C11A C9B
EADP C12A C8B
FMAP    2
PLAN    10
WGHT    0.033400    0.498000
EXTI    0.042762
FVAR       0.25935   0.67535
F2    4    0.508358    0.090204   -0.343420    11.00000    0.04777    0.02213 =
         0.02614    0.01263    0.01412    0.01984
PART 1
F1A   4    0.933822    0.468313   -0.194605    21.00000    0.04177    0.02761 =
         0.03472    0.01850    0.01380    0.01505
C7A   1    0.985974    0.706896   -0.132875    21.00000    0.02169    0.06500 =
         0.02887    0.02976    0.01436    0.02428
C8A   1    0.943712    0.564042   -0.229940    21.00000    0.01926    0.06350 =
         0.03768    0.03582    0.01133    0.01362
C9A   1    0.909637    0.524557   -0.356190    21.00000    0.02619    0.06139 =
         0.03149    0.02499    0.01076    0.01546
AFIX  43
H9A   2    0.883342    0.425613   -0.419755    21.00000   -1.20000
AFIX   0
C10A  1    0.914550    0.631827   -0.388220    21.00000    0.04539    0.08526 =
         0.03402    0.04019    0.02227    0.03952
AFIX  43
H10A  2    0.891368    0.607065   -0.474529    21.00000   -1.20000
AFIX   0
C11A  1    0.953129    0.774769   -0.294766    21.00000    0.06477    0.08470 =
         0.04248    0.04710    0.03384    0.05509
AFIX  43
H11A  2    0.954429    0.848180   -0.316590    21.00000   -1.20000
AFIX   0
C12A  1    0.989990    0.811343   -0.169066    21.00000    0.05320    0.07860 =
         0.03909    0.03914    0.02981    0.04898
AFIX  43
H12A  2    1.018931    0.911033   -0.105617    21.00000   -1.20000
AFIX   0
PART 2
F1B   4    1.007440    0.919858   -0.089858   -21.00000    0.04177    0.02761 =
         0.03472    0.01850    0.01380    0.01505
C7B   1    0.985974    0.706896   -0.132875   -21.00000    0.02169    0.06500 =
         0.02887    0.02976    0.01436    0.02428
C8B   1    0.989990    0.811343   -0.169066   -21.00000    0.05320    0.07860 =
         0.03909    0.03914    0.02981    0.04898
C9B   1    0.953129    0.774769   -0.294766   -21.00000    0.06477    0.08470 =
         0.04248    0.04710    0.03384    0.05509
AFIX  43
H9B   2    0.954429    0.848180   -0.316590   -21.00000   -1.20000
AFIX   0
 
C10B  1    0.914550    0.631827   -0.388220   -21.00000    0.04539    0.08526 =
         0.03402    0.04019    0.02227    0.03952
AFIX  43
H10B  2    0.891368    0.607065   -0.474529   -21.00000   -1.20000
AFIX   0
C11B  1    0.909637    0.524557   -0.356190   -21.00000    0.02619    0.06139 =
         0.03149    0.02499    0.01076    0.01546
AFIX  43
H11B  2    0.883342    0.425613   -0.419755   -21.00000   -1.20000
AFIX   0
C12B  1    0.943712    0.564042   -0.229940   -21.00000    0.01926    0.06350 =
         0.03768    0.03582    0.01133    0.01362
AFIX  43
H12B  2    0.937844    0.489215   -0.208555   -21.00000   -1.20000
AFIX   0
 
PART 0
N1    3    1.031715    0.742767   -0.005251    11.00000    0.02349    0.05689 =
         0.02887    0.02820    0.01303    0.02165
N2    3    0.795316    0.719169    0.011136    11.00000    0.02263    0.04456 =
         0.02486    0.02103    0.01114    0.01952
AFIX  93
H2A   2    0.763262    0.695148   -0.068176    11.00000   -1.20000
H2B   2    0.735389    0.724488    0.059544    11.00000   -1.20000
AFIX   0
N3    3    0.472933    0.281260   -0.122900    11.00000    0.01981    0.02079 =
         0.01836    0.01053    0.00685    0.01020
N4    3    0.723370    0.329079   -0.065889    11.00000    0.01927    0.03617 =
         0.02631    0.02206    0.00785    0.01202
AFIX  93
H4A   2    0.746718    0.362844   -0.118779    11.00000   -1.20000
H4B   2    0.791917    0.326098   -0.018372    11.00000   -1.20000
AFIX   0
C1    1    0.980436    0.786254    0.192760    11.00000    0.02290    0.02352 =
         0.02476    0.01404    0.01000    0.01359
C2    1    0.874982    0.733546    0.248411    11.00000    0.02155    0.03952 =
         0.03206    0.02278    0.01060    0.01508
AFIX  43
H2    2    0.773435    0.671875    0.199847    11.00000   -1.20000
AFIX   0
C3    1    0.916183    0.769844    0.373627    11.00000    0.03232    0.05296 =
         0.03439    0.02958    0.01917    0.02251
AFIX  43
H3    2    0.842905    0.734025    0.410852    11.00000   -1.20000
AFIX   0
C4    1    1.063539    0.857993    0.444562    11.00000    0.03986    0.04412 =
         0.02285    0.01668    0.01200    0.02087
AFIX  43
H4    2    1.092000    0.883453    0.530738    11.00000   -1.20000
AFIX   0
C5    1    1.169537    0.909061    0.389557    11.00000    0.02890    0.03681 =
         0.02604    0.01208    0.00383    0.00641
AFIX  43
H5    2    1.271350    0.968448    0.437819    11.00000   -1.20000
AFIX   0
C6    1    1.128448    0.874335    0.264843    11.00000    0.02457    0.03206 =
         0.02703    0.01571    0.00943    0.00760
AFIX  43
H6    2    1.202020    0.911007    0.228203    11.00000   -1.20000
AFIX   0
 
C13   1    0.935396    0.747650    0.058200    11.00000    0.02045    0.02443 =
         0.02757    0.01646    0.00919    0.01143
C14   1    0.554224    0.232029    0.037574    11.00000    0.02241    0.01955 =
         0.01910    0.00946    0.00891    0.01387
C15   1    0.664954    0.292552    0.148252    11.00000    0.02236    0.02334 =
         0.02178    0.01076    0.00713    0.01245
AFIX  43
H15   2    0.760679    0.368192    0.164548    11.00000   -1.20000
AFIX   0
C16   1    0.636079    0.242845    0.234877    11.00000    0.03300    0.03052 =
         0.01989    0.01196    0.00652    0.01901
AFIX  43
H16   2    0.712429    0.283503    0.309736    11.00000   -1.20000
AFIX   0
C17   1    0.495938    0.133905    0.212349    11.00000    0.04086    0.02965 =
         0.02307    0.01796    0.01566    0.02121
AFIX  43
H17   2    0.476171    0.100183    0.271858    11.00000   -1.20000
AFIX   0
C18   1    0.384614    0.074206    0.102794    11.00000    0.02901    0.02263 =
         0.02819    0.01519    0.01382    0.01360
AFIX  43
H18   2    0.288278    0.000323    0.087721    11.00000   -1.20000
AFIX   0
C19   1    0.413790    0.122195    0.015461    11.00000    0.02256    0.02035 =
         0.02077    0.01013    0.00744    0.01241
AFIX  43
H19   2    0.337683    0.080049   -0.059989    11.00000   -1.20000
AFIX   0
C20   1    0.498528    0.316641   -0.220268    11.00000    0.01389    0.02124 =
         0.01869    0.01034    0.00406    0.00677
C21   1    0.513119    0.219927   -0.331800    11.00000    0.02327    0.01783 =
         0.02250    0.01006    0.00511    0.00937
C22   1    0.530466    0.247613   -0.430732    11.00000    0.02899    0.02662 =
         0.01758    0.00924    0.00673    0.01183
AFIX  43
H22   2    0.541109    0.178564   -0.504696    11.00000   -1.20000
AFIX   0
C23   1    0.532207    0.378024   -0.420993    11.00000    0.02837    0.03243 =
         0.02440    0.01925    0.00853    0.01263
AFIX  43
H23   2    0.543766    0.399116   -0.488496    11.00000   -1.20000
AFIX   0
C24   1    0.516965    0.477132   -0.312113    11.00000    0.02717    0.02635 =
         0.03234    0.01922    0.01022    0.01398
AFIX  43
H24   2    0.517805    0.566488   -0.304954    11.00000   -1.20000
AFIX   0
C25   1    0.500470    0.446536   -0.213413    11.00000    0.02019    0.02211 =
         0.02387    0.01091    0.00787    0.01091
AFIX  43
H25   2    0.490244    0.515809   -0.139323    11.00000   -1.20000
AFIX   0
C26   1    0.582982    0.282048   -0.057682    11.00000    0.01989    0.01633 =
         0.01731    0.00658    0.00603    0.00887
HKLF   4
 
END  
;

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.50836(9) 0.09020(8) -0.34342(7) 0.02999(19) Uani 1 1 d . . .
F1A F 0.93382(13) 0.46831(12) -0.19460(11) 0.0333(3) Uani 0.6754(15) 1 d P A 1
C7A C 0.98597(14) 0.70690(18) -0.13288(13) 0.0336(3) Uani 0.6754(15) 1 d P A 1
C8A C 0.94371(15) 0.56404(19) -0.22994(14) 0.0371(4) Uani 0.6754(15) 1 d P A 1
C9A C 0.90964(16) 0.52456(19) -0.35619(14) 0.0400(4) Uani 0.6754(15) 1 d P A 1
H9A H 0.8833 0.4256 -0.4198 0.048 Uiso 0.6754(15) 1 calc PR A 1
C10A C 0.91455(18) 0.6318(2) -0.38822(15) 0.0462(4) Uani 0.6754(15) 1 d P A 1
H10A H 0.8914 0.6071 -0.4745 0.055 Uiso 0.6754(15) 1 calc PR A 1
C11A C 0.9531(2) 0.7748(2) -0.29477(16) 0.0489(4) Uani 0.6754(15) 1 d P A 1
H11A H 0.9544 0.8482 -0.3166 0.059 Uiso 0.6754(15) 1 calc PR A 1
C12A C 0.98999(19) 0.8113(2) -0.16907(15) 0.0450(4) Uani 0.6754(15) 1 d P A 1
H12A H 1.0189 0.9110 -0.1056 0.054 Uiso 0.6754(15) 1 calc PR A 1
F1B F 1.0074(3) 0.9199(3) -0.0899(2) 0.0333(3) Uani 0.3246(15) 1 d P A 2
C7B C 0.98597(14) 0.70690(18) -0.13288(13) 0.0336(3) Uani 0.3246(15) 1 d P A 2
C8B C 0.98999(19) 0.8113(2) -0.16907(15) 0.0450(4) Uani 0.3246(15) 1 d P A 2
C9B C 0.9531(2) 0.7748(2) -0.29477(16) 0.0489(4) Uani 0.3246(15) 1 d P A 2
H9B H 0.9544 0.8482 -0.3166 0.059 Uiso 0.3246(15) 1 calc PR A 2
C10B C 0.91455(18) 0.6318(2) -0.38822(15) 0.0462(4) Uani 0.3246(15) 1 d P A 2
H10B H 0.8914 0.6071 -0.4745 0.055 Uiso 0.3246(15) 1 calc PR A 2
C11B C 0.90964(16) 0.52456(19) -0.35619(14) 0.0400(4) Uani 0.3246(15) 1 d P A 2
H11B H 0.8833 0.4256 -0.4198 0.048 Uiso 0.3246(15) 1 calc PR A 2
C12B C 0.94371(15) 0.56404(19) -0.22994(14) 0.0371(4) Uani 0.3246(15) 1 d P A 2
H12B H 0.9378 0.4892 -0.2086 0.045 Uiso 0.3246(15) 1 calc PR A 2
N1 N 1.03172(12) 0.74277(14) -0.00525(11) 0.0319(3) Uani 1 1 d . . .
N2 N 0.79532(12) 0.71917(13) 0.01114(10) 0.0272(2) Uani 1 1 d . . .
H2A H 0.7633 0.6951 -0.0682 0.033 Uiso 1 1 calc R A .
H2B H 0.7354 0.7245 0.0595 0.033 Uiso 1 1 calc R . .
N3 N 0.47293(11) 0.28126(10) -0.12290(9) 0.0188(2) Uani 1 1 d . . .
N4 N 0.72337(11) 0.32908(12) -0.06589(10) 0.0246(2) Uani 1 1 d . . .
H4A H 0.7467 0.3628 -0.1188 0.029 Uiso 1 1 calc R . .
H4B H 0.7919 0.3261 -0.0184 0.029 Uiso 1 1 calc R . .
C1 C 0.98044(13) 0.78625(13) 0.19276(11) 0.0215(3) Uani 1 1 d . . .
C2 C 0.87498(14) 0.73355(15) 0.24841(13) 0.0282(3) Uani 1 1 d . A .
H2 H 0.7734 0.6719 0.1998 0.034 Uiso 1 1 calc R . .
C3 C 0.91618(16) 0.76984(17) 0.37363(13) 0.0347(3) Uani 1 1 d . . .
H3 H 0.8429 0.7340 0.4109 0.042 Uiso 1 1 calc R A .
C4 C 1.06354(16) 0.85799(17) 0.44456(13) 0.0346(3) Uani 1 1 d . A .
H4 H 1.0920 0.8835 0.5307 0.041 Uiso 1 1 calc R . .
C5 C 1.16954(16) 0.90906(16) 0.38956(13) 0.0350(3) Uani 1 1 d . . .
H5 H 1.2713 0.9684 0.4378 0.042 Uiso 1 1 calc R A .
C6 C 1.12845(14) 0.87434(15) 0.26484(12) 0.0289(3) Uani 1 1 d . A .
H6 H 1.2020 0.9110 0.2282 0.035 Uiso 1 1 calc R . .
C13 C 0.93540(13) 0.74765(13) 0.05820(12) 0.0220(3) Uani 1 1 d . A .
C14 C 0.55422(13) 0.23203(13) 0.03757(11) 0.0186(2) Uani 1 1 d . . .
C15 C 0.66495(14) 0.29255(13) 0.14825(11) 0.0218(3) Uani 1 1 d . . .
H15 H 0.7607 0.3682 0.1645 0.026 Uiso 1 1 calc R . .
C16 C 0.63608(15) 0.24285(14) 0.23488(12) 0.0264(3) Uani 1 1 d . . .
H16 H 0.7124 0.2835 0.3097 0.032 Uiso 1 1 calc R . .
C17 C 0.49594(15) 0.13390(14) 0.21235(12) 0.0268(3) Uani 1 1 d . . .
H17 H 0.4762 0.1002 0.2719 0.032 Uiso 1 1 calc R . .
C18 C 0.38461(14) 0.07421(14) 0.10279(12) 0.0244(3) Uani 1 1 d . . .
H18 H 0.2883 0.0003 0.0877 0.029 Uiso 1 1 calc R . .
C19 C 0.41379(13) 0.12219(13) 0.01546(11) 0.0201(3) Uani 1 1 d . . .
H19 H 0.3377 0.0800 -0.0600 0.024 Uiso 1 1 calc R . .
C20 C 0.49853(12) 0.31664(13) -0.22027(11) 0.0181(2) Uani 1 1 d . . .
C21 C 0.51312(13) 0.21993(13) -0.33180(11) 0.0212(3) Uani 1 1 d . . .
C22 C 0.53047(14) 0.24761(14) -0.43073(11) 0.0252(3) Uani 1 1 d . . .
H22 H 0.5411 0.1786 -0.5047 0.030 Uiso 1 1 calc R . .
C23 C 0.53221(14) 0.37802(14) -0.42099(12) 0.0265(3) Uani 1 1 d . . .
H23 H 0.5438 0.3991 -0.4885 0.032 Uiso 1 1 calc R . .
C24 C 0.51696(14) 0.47713(14) -0.31211(12) 0.0259(3) Uani 1 1 d . . .
H24 H 0.5178 0.5665 -0.3050 0.031 Uiso 1 1 calc R . .
C25 C 0.50047(13) 0.44654(13) -0.21341(12) 0.0216(3) Uani 1 1 d . . .
H25 H 0.4902 0.5158 -0.1393 0.026 Uiso 1 1 calc R . .
C26 C 0.58298(13) 0.28205(12) -0.05768(11) 0.0182(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C21 1.3609(13) . ?
F1A C8A 1.2754(18) . ?
C7A C8A 1.384(2) . ?
C7A C12A 1.387(2) . ?
C7A N1 1.4168(17) . ?
C8A C9A 1.380(2) . ?
C9A C10A 1.381(2) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.377(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.384(2) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
N1 C13 1.2943(16) . ?
N2 C13 1.3402(16) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 C26 1.3000(15) . ?
N3 C20 1.4131(15) . ?
N4 C26 1.3444(15) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C1 C6 1.3874(18) . ?
C1 C2 1.3899(17) . ?
C1 C13 1.4876(17) . ?
C2 C3 1.3824(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3815(19) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C14 C15 1.3917(17) . ?
C14 C19 1.3941(17) . ?
C14 C26 1.4892(16) . ?
C15 C16 1.3874(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3867(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.3875(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.3839(17) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.3911(17) . ?
C20 C25 1.3939(16) . ?
C21 C22 1.3730(17) . ?
C22 C23 1.3876(18) . ?
C22 H22 0.9500 . ?
C23 C24 1.3842(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.3871(17) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
C8A C7A C12A 116.05(13) . . ?
C8A C7A N1 120.47(13) . . ?
C12A C7A N1 123.34(15) . . ?
F1A C8A C9A 121.59(16) . . ?
F1A C8A C7A 114.92(13) . . ?
C9A C8A C7A 123.46(15) . . ?
C8A C9A C10A 118.65(16) . . ?
C8A C9A H9A 120.7 . . ?
C10A C9A H9A 120.7 . . ?
C11A C10A C9A 119.86(14) . . ?
C11A C10A H10A 120.1 . . ?
C9A C10A H10A 120.1 . . ?
C10A C11A C12A 119.94(16) . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C11A C12A C7A 122.01(17) . . ?
C11A C12A H12A 119.0 . . ?
C7A C12A H12A 119.0 . . ?
C13 N1 C7A 117.46(11) . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C26 N3 C20 117.27(10) . . ?
C26 N4 H4A 120.0 . . ?
C26 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C6 C1 C2 118.69(12) . . ?
C6 C1 C13 120.76(11) . . ?
C2 C1 C13 120.55(11) . . ?
C3 C2 C1 120.75(12) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.07(12) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.61(13) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.44(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.43(12) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N1 C13 N2 124.61(12) . . ?
N1 C13 C1 118.75(11) . . ?
N2 C13 C1 116.64(10) . . ?
C15 C14 C19 119.28(11) . . ?
C15 C14 C26 121.29(11) . . ?
C19 C14 C26 119.43(10) . . ?
C16 C15 C14 120.25(11) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.10(12) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.93(11) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.06(12) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.38(11) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C21 C20 C25 116.06(11) . . ?
C21 C20 N3 122.22(10) . . ?
C25 C20 N3 121.59(10) . . ?
F2 C21 C22 118.48(10) . . ?
F2 C21 C20 117.89(10) . . ?
C22 C21 C20 123.62(11) . . ?
C21 C22 C23 118.96(11) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C24 C23 C22 119.45(11) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 120.28(11) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 121.62(11) . . ?
C24 C25 H25 119.2 . . ?
C20 C25 H25 119.2 . . ?
N3 C26 N4 125.39(11) . . ?
N3 C26 C14 118.01(10) . . ?
N4 C26 C14 116.56(10) . . ?

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
C12A C7A C8A F1A -176.75(12) . . . . ?
N1 C7A C8A F1A 7.46(18) . . . . ?
C12A C7A C8A C9A 1.2(2) . . . . ?
N1 C7A C8A C9A -174.56(12) . . . . ?
F1A C8A C9A C10A 176.38(13) . . . . ?
C7A C8A C9A C10A -1.5(2) . . . . ?
C8A C9A C10A C11A 0.1(2) . . . . ?
C9A C10A C11A C12A 1.4(2) . . . . ?
C10A C11A C12A C7A -1.7(2) . . . . ?
C8A C7A C12A C11A 0.4(2) . . . . ?
N1 C7A C12A C11A 176.01(14) . . . . ?
C8A C7A N1 C13 -100.54(15) . . . . ?
C12A C7A N1 C13 83.98(17) . . . . ?
C6 C1 C2 C3 0.94(19) . . . . ?
C13 C1 C2 C3 -179.62(12) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C2 C1 C6 C5 -0.22(19) . . . . ?
C13 C1 C6 C5 -179.66(12) . . . . ?
C7A N1 C13 N2 1.0(2) . . . . ?
C7A N1 C13 C1 -179.49(12) . . . . ?
C6 C1 C13 N1 27.33(18) . . . . ?
C2 C1 C13 N1 -152.10(13) . . . . ?
C6 C1 C13 N2 -153.11(12) . . . . ?
C2 C1 C13 N2 27.46(17) . . . . ?
C19 C14 C15 C16 0.66(17) . . . . ?
C26 C14 C15 C16 -179.20(10) . . . . ?
C14 C15 C16 C17 -0.88(18) . . . . ?
C15 C16 C17 C18 0.22(18) . . . . ?
C16 C17 C18 C19 0.66(18) . . . . ?
C17 C18 C19 C14 -0.88(17) . . . . ?
C15 C14 C19 C18 0.22(17) . . . . ?
C26 C14 C19 C18 -179.92(10) . . . . ?
C26 N3 C20 C21 71.43(14) . . . . ?
C26 N3 C20 C25 -113.01(12) . . . . ?
C25 C20 C21 F2 -178.53(10) . . . . ?
N3 C20 C21 F2 -2.75(17) . . . . ?
C25 C20 C21 C22 0.79(17) . . . . ?
N3 C20 C21 C22 176.57(11) . . . . ?
F2 C21 C22 C23 178.61(11) . . . . ?
C20 C21 C22 C23 -0.71(19) . . . . ?
C21 C22 C23 C24 0.20(19) . . . . ?
C22 C23 C24 C25 0.17(19) . . . . ?
C23 C24 C25 C20 -0.06(19) . . . . ?
C21 C20 C25 C24 -0.39(17) . . . . ?
N3 C20 C25 C24 -176.20(11) . . . . ?
C20 N3 C26 N4 7.59(17) . . . . ?
C20 N3 C26 C14 -174.68(9) . . . . ?
C15 C14 C26 N3 -147.97(11) . . . . ?
C19 C14 C26 N3 32.18(15) . . . . ?
C15 C14 C26 N4 29.97(15) . . . . ?
C19 C14 C26 N4 -149.89(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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_DB01_II
_audit_block_doi                 10.5517/cc133n51
_database_code_depnum_ccdc_archive 'CCDC 1016402'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5CC09741J 2016
_audit_update_record             
;
2014-07-28 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 F N2'
_chemical_formula_weight         214.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9351(8)
_cell_length_b                   11.8469(9)
_cell_length_c                   15.2049(12)
_cell_angle_alpha                96.758(2)
_cell_angle_beta                 109.718(2)
_cell_angle_gamma                113.790(2)
_cell_volume                     1621.4(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      30.51

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            59699
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         30.63
_reflns_number_total             9959
_reflns_number_gt                7724
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0646P)²+0.7986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9959
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_iucr_refine_instruction_details 
;
TITL DB01_H in P-1
CELL 0.71073 10.9351 11.8469 15.2049 96.758 109.718 113.790
ZERR 6.00 0.0008 0.0009 0.0012 0.002 0.002 0.002
LATT 1
SFAC C H N F
UNIT 78 66 12 6
L.S. 12
OMIT 1 0 0
ACTA
BOND $H
CONF
HTAB
SIZE 0.40 0.32 0.13
TEMP -173
EADP F2A F2B
EXYZ C20A C20B
EXYZ C21A C25B
EXYZ C22A C24B
EXYZ C23A C23B
EXYZ C24A C22B
EXYZ C25A C21B
EADP C20A C20B
EADP C21A C25B
EADP C22A C24B
EADP C23A C23B
EADP C24A C22B
EADP C25A C21B
FMAP 2
PLAN 5
WGHT    0.064600    0.798600
FVAR       0.16989   0.60169
PART 1
F2A   4   -0.042341    0.319704    0.425773    21.00000    0.02809    0.03178 =
         0.05340    0.01450    0.01539    0.01430
C20A  1    0.190617    0.365356    0.464059    21.00000    0.06582    0.01896 =
         0.01647    0.00916    0.01876    0.01933
C21A  1    0.043201    0.275609    0.426797    21.00000    0.06548    0.02714 =
         0.02241    0.00973    0.00541    0.02195
C22A  1   -0.010200    0.145057    0.385996    21.00000    0.06965    0.02357 =
         0.02797    0.00686    0.00685    0.01291
AFIX  43
H22A  2   -0.112303    0.086374    0.362096    21.00000   -1.20000
AFIX   0
C23A  1    0.087049    0.102089    0.380741    21.00000    0.09558    0.01975 =
         0.03948    0.00955    0.03456    0.02276
AFIX  43
H23A  2    0.052583    0.013053    0.352499    21.00000   -1.20000
AFIX   0
C24A  1    0.234860    0.188488    0.416558    21.00000    0.09545    0.02653 =
         0.06251    0.01935    0.05723    0.03182
AFIX  43
H24A  2    0.302333    0.159049    0.412573    21.00000   -1.20000
AFIX   0
C25A  1    0.285534    0.318543    0.458487    21.00000    0.08242    0.02417 =
         0.04952    0.01696    0.04791    0.02470
AFIX  43
H25A  2    0.388049    0.376705    0.483957    21.00000   -1.20000
AFIX   0
PART 2
F2B   4    0.404012    0.397399    0.482004   -21.00000    0.02809    0.03178 =
         0.05340    0.01450    0.01539    0.01430
C20B  1    0.190617    0.365356    0.464059   -21.00000    0.06582    0.01896 =
         0.01647    0.00916    0.01876    0.01933
C21B  1    0.285534    0.318543    0.458487   -21.00000    0.08242    0.02417 =
         0.04952    0.01696    0.04791    0.02470
C22B  1    0.234860    0.188488    0.416558   -21.00000    0.09545    0.02653 =
         0.06251    0.01935    0.05723    0.03182
AFIX  43
H22B  2    0.302333    0.159049    0.412573   -21.00000   -1.20000
AFIX   0
C23B  1    0.087049    0.102089    0.380741   -21.00000    0.09558    0.01975 =
         0.03948    0.00955    0.03456    0.02276
AFIX  43
H23B  2    0.052583    0.013053    0.352499   -21.00000   -1.20000
AFIX   0
C24B  1   -0.010200    0.145057    0.385996   -21.00000    0.06965    0.02357 =
         0.02797    0.00686    0.00685    0.01291
AFIX  43
H24B  2   -0.112303    0.086374    0.362096   -21.00000   -1.20000
AFIX   0
C25B  1    0.043201    0.275609    0.426797   -21.00000    0.06548    0.02714 =
         0.02241    0.00973    0.00541    0.02195
AFIX  43
H25B  2   -0.024975    0.304914    0.429285   -21.00000   -1.20000
AFIX   0
PART 0
F3    4    0.618354    0.141230    0.860766    11.00000    0.02294    0.02503 =
         0.04529    0.01685    0.02210    0.01289
F1    4    0.471927    0.829627    0.892050    11.00000    0.02707    0.02601 =
         0.06683    0.01476    0.02929    0.01375
N3    3    0.241379    0.497376    0.509696    11.00000    0.05061    0.01967 =
         0.01719    0.00701    0.01349    0.01826
N4    3    0.184442    0.528419    0.354947    11.00000    0.04415    0.02059 =
         0.01735    0.00903    0.01539    0.01402
AFIX  93
H4A   2    0.150935    0.446607    0.325558    11.00000   -1.20000
H4B   2    0.184019    0.582922    0.320348    11.00000   -1.20000
AFIX   0
N1    3    0.245756    0.587527    0.859217    11.00000    0.02538    0.01694 =
         0.01774    0.00727    0.01209    0.01138
N2    3    0.208299    0.562822    0.695692    11.00000    0.05203    0.03639 =
         0.01855    0.01307    0.01738    0.03476
AFIX  93
H2A   2    0.188300    0.627543    0.692794    11.00000   -1.20000
H2B   2    0.207004    0.519440    0.643965    11.00000   -1.20000
AFIX   0
N5    3    0.777974    0.349053    0.804023    11.00000    0.02019    0.01567 =
         0.01600    0.00674    0.00933    0.01033
N6    3    0.815131    0.416907    0.966717    11.00000    0.03044    0.02560 =
         0.01622    0.00945    0.01177    0.01948
AFIX  93
H6A   2    0.853434    0.366421    0.985204    11.00000   -1.20000
H6B   2    0.806339    0.466439    1.009487    11.00000   -1.20000
AFIX   0
C36   1    0.902209    0.060023    0.857841    11.00000    0.02677    0.01786 =
         0.02652    0.00621    0.00906    0.01424
AFIX  43
H36   2    0.929572   -0.005511    0.868417    11.00000   -1.20000
AFIX   0
C35   1    0.984818    0.161964    0.830787    11.00000    0.02061    0.02120 =
         0.02389    0.00427    0.00998    0.01198
AFIX  43
H35   2    1.068697    0.165923    0.822616    11.00000   -1.20000
AFIX   0
C34   1    0.945187    0.258198    0.815628    11.00000    0.01988    0.01708 =
         0.01849    0.00537    0.00966    0.00859
AFIX  43
H34   2    1.003464    0.327713    0.797856    11.00000   -1.20000
AFIX   0
C33   1    0.821852    0.255129    0.825893    11.00000    0.01788    0.01469 =
         0.01290    0.00396    0.00603    0.00798
C39   1    0.770005    0.418365    0.873043    11.00000    0.01536    0.01504 =
         0.01604    0.00668    0.00754    0.00696
C27   1    0.715526    0.512434    0.849472    11.00000    0.01585    0.01559 =
         0.01815    0.00738    0.00938    0.00839
C28   1    0.764310    0.624966    0.921280    11.00000    0.02133    0.01876 =
         0.01771    0.00438    0.00701    0.01047
AFIX  43
H28   2    0.831942    0.641531    0.986106    11.00000   -1.20000
AFIX   0
C29   1    0.713866    0.713004    0.897931    11.00000    0.02992    0.01927 =
         0.02470    0.00420    0.01160    0.01404
AFIX  43
H29   2    0.746558    0.789319    0.947010    11.00000   -1.20000
AFIX   0
C30   1    0.616171    0.689639    0.803366    11.00000    0.02744    0.02205 =
         0.02780    0.01059    0.01278    0.01672
AFIX  43
H30   2    0.583021    0.750507    0.787486    11.00000   -1.20000
AFIX   0
C37   1    0.779714    0.054571    0.869288    11.00000    0.02563    0.01598 =
         0.02776    0.00944    0.01224    0.00937
AFIX  43
H37   2    0.722887   -0.013962    0.888531    11.00000   -1.20000
AFIX   0
C38   1    0.741555    0.150241    0.852302    11.00000    0.01772    0.01746 =
         0.02206    0.00652    0.00987    0.00840
C32   1    0.615454    0.488606    0.754666    11.00000    0.01869    0.01745 =
         0.01754    0.00560    0.00875    0.00895
AFIX  43
H32   2    0.580705    0.411445    0.705732    11.00000   -1.20000
AFIX   0
C31   1    0.566476    0.577239    0.731582    11.00000    0.02161    0.02385 =
         0.01964    0.00922    0.00825    0.01365
AFIX  43
H31   2    0.499059    0.561133    0.666795    11.00000   -1.20000
AFIX   0
C17   1    0.388363    0.969348    0.580365    11.00000    0.07732    0.02225 =
         0.05709    0.00657    0.02685    0.02495
AFIX  43
H17   2    0.425894    1.059134    0.607962    11.00000   -1.20000
AFIX   0
C18   1    0.280381    0.906789    0.486376    11.00000    0.10562    0.03829 =
         0.05529    0.02094    0.02491    0.04911
AFIX  43
H18   2    0.239828    0.952913    0.449984    11.00000   -1.20000
AFIX   0
C19   1    0.230073    0.777056    0.444171    11.00000    0.07082    0.03390 =
         0.03080    0.01132    0.00881    0.03327
AFIX  43
H19   2    0.154953    0.734643    0.379365    11.00000   -1.20000
AFIX   0
C14   1    0.289362    0.709333    0.496513    11.00000    0.02770    0.01919 =
         0.02171    0.00824    0.01267    0.01366
C26   1    0.236299    0.570158    0.452740    11.00000    0.02309    0.01954 =
         0.01709    0.00644    0.01019    0.01090
C15   1    0.392679    0.771418    0.591177    11.00000    0.05521    0.02586 =
         0.03376   -0.00155   -0.01033    0.02275
AFIX  43
H15   2    0.431965    0.725303    0.628474    11.00000   -1.20000
AFIX   0
C16   1    0.440877    0.900505    0.633472    11.00000    0.07213    0.02945 =
         0.04804   -0.01118   -0.01430    0.02385
AFIX  43
H16   2    0.510860    0.941398    0.699797    11.00000   -1.20000
AFIX   0
C10   1    0.189519    0.921154    0.876969    11.00000    0.03308    0.02214 =
         0.03023    0.01195    0.01763    0.01825
AFIX  43
H10   2    0.177031    0.996144    0.881595    11.00000   -1.20000
AFIX   0
C9    1    0.324792    0.930604    0.888496    11.00000    0.02878    0.01783 =
         0.03369    0.01008    0.01817    0.01058
AFIX  43
H9    2    0.406283    1.011920    0.901871    11.00000   -1.20000
AFIX   0
C8    1    0.339049    0.819739    0.880197    11.00000    0.02332    0.02179 =
         0.02905    0.00911    0.01692    0.01211
C7    1    0.224235    0.697818    0.860980    11.00000    0.02398    0.01807 =
         0.01458    0.00643    0.01067    0.01122
C13   1    0.240844    0.530205    0.779184    11.00000    0.01845    0.01856 =
         0.01714    0.00607    0.00843    0.00946
C1    1    0.270362    0.417775    0.777819    11.00000    0.01834    0.01669 =
         0.01865    0.00691    0.01052    0.00861
C6    1    0.358901    0.408799    0.864855    11.00000    0.01857    0.02006 =
         0.02012    0.00713    0.00791    0.00943
AFIX  43
H6    2    0.397550    0.472931    0.924695    11.00000   -1.20000
AFIX   0
C5    1    0.390644    0.306456    0.864233    11.00000    0.02133    0.02413 =
         0.02867    0.01281    0.01079    0.01299
AFIX  43
H5    2    0.451070    0.300923    0.923619    11.00000   -1.20000
AFIX   0
C4    1    0.334381    0.212302    0.777163    11.00000    0.02801    0.01957 =
         0.03720    0.01231    0.01951    0.01394
AFIX  43
H4    2    0.357506    0.143133    0.776710    11.00000   -1.20000
AFIX   0
C11   1    0.072338    0.801762    0.858642    11.00000    0.02487    0.02773 =
         0.02632    0.01197    0.01253    0.01683
AFIX  43
H11   2   -0.020342    0.795184    0.851156    11.00000   -1.20000
AFIX   0
C12   1    0.089926    0.691793    0.851190    11.00000    0.02080    0.02037 =
         0.01772    0.00784    0.00800    0.00941
AFIX  43
H12   2    0.008911    0.610815    0.839185    11.00000   -1.20000
AFIX   0
C3    1    0.244263    0.219458    0.690771    11.00000    0.03265    0.01796 =
         0.02704    0.00503    0.01672    0.01124
AFIX  43
H3    2    0.204625    0.154444    0.631228    11.00000   -1.20000
AFIX   0
C2    1    0.211776    0.321363    0.691021    11.00000    0.02552    0.02131 =
         0.01874    0.00660    0.01096    0.01098
AFIX  43
H2    2    0.149295    0.325337    0.631708    11.00000   -1.20000
HKLF   4
 

END  
;

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F2A F -0.04234(17) 0.31970(15) 0.42577(13) 0.0381(3) Uani 0.6017(18) 1 d P A 1
C20A C 0.1906(2) 0.36536(13) 0.46406(10) 0.0332(4) Uani 0.6017(18) 1 d P A 1
C21A C 0.0432(2) 0.27561(16) 0.42680(12) 0.0421(4) Uani 0.6017(18) 1 d P A 1
C22A C -0.0102(2) 0.14506(16) 0.38600(13) 0.0480(5) Uani 0.6017(18) 1 d P A 1
H22A H -0.1123 0.0864 0.3621 0.058 Uiso 0.6017(18) 1 calc PR A 1
C23A C 0.0870(3) 0.10209(16) 0.38074(14) 0.0514(5) Uani 0.6017(18) 1 d P A 1
H23A H 0.0526 0.0131 0.3525 0.062 Uiso 0.6017(18) 1 calc PR A 1
C24A C 0.2349(3) 0.18849(17) 0.41656(16) 0.0526(5) Uani 0.6017(18) 1 d P A 1
H24A H 0.3023 0.1590 0.4126 0.063 Uiso 0.6017(18) 1 calc PR A 1
C25A C 0.2855(3) 0.31854(16) 0.45849(14) 0.0456(5) Uani 0.6017(18) 1 d P A 1
H25A H 0.3880 0.3767 0.4840 0.055 Uiso 0.6017(18) 1 calc PR A 1
F2B F 0.4040(3) 0.3974(2) 0.4820(2) 0.0381(3) Uani 0.3983(18) 1 d P A 2
C20B C 0.1906(2) 0.36536(13) 0.46406(10) 0.0332(4) Uani 0.3983(18) 1 d P A 2
C21B C 0.2855(3) 0.31854(16) 0.45849(14) 0.0456(5) Uani 0.3983(18) 1 d P A 2
C22B C 0.2349(3) 0.18849(17) 0.41656(16) 0.0526(5) Uani 0.3983(18) 1 d P A 2
H22B H 0.3023 0.1590 0.4126 0.063 Uiso 0.3983(18) 1 calc PR A 2
C23B C 0.0870(3) 0.10209(16) 0.38074(14) 0.0514(5) Uani 0.3983(18) 1 d P A 2
H23B H 0.0526 0.0131 0.3525 0.062 Uiso 0.3983(18) 1 calc PR A 2
C24B C -0.0102(2) 0.14506(16) 0.38600(13) 0.0480(5) Uani 0.3983(18) 1 d P A 2
H24B H -0.1123 0.0864 0.3621 0.058 Uiso 0.3983(18) 1 calc PR A 2
C25B C 0.0432(2) 0.27561(16) 0.42680(12) 0.0421(4) Uani 0.3983(18) 1 d P A 2
H25B H -0.0250 0.3049 0.4293 0.051 Uiso 0.3983(18) 1 calc PR A 2
F3 F 0.61835(9) 0.14123(8) 0.86077(7) 0.02757(19) Uani 1 1 d . . .
F1 F 0.47193(10) 0.82963(8) 0.89205(8) 0.0366(2) Uani 1 1 d . . .
N3 N 0.24138(15) 0.49738(11) 0.50970(8) 0.0287(3) Uani 1 1 d . . .
N4 N 0.18444(14) 0.52842(11) 0.35495(8) 0.0268(3) Uani 1 1 d . . .
H4A H 0.1509 0.4466 0.3256 0.032 Uiso 1 1 calc R A .
H4B H 0.1840 0.5829 0.3203 0.032 Uiso 1 1 calc R . .
N1 N 0.24576(12) 0.58753(10) 0.85922(8) 0.0184(2) Uani 1 1 d . . .
N2 N 0.20830(15) 0.56282(13) 0.69569(8) 0.0293(3) Uani 1 1 d . . .
H2A H 0.1883 0.6275 0.6928 0.035 Uiso 1 1 calc R . .
H2B H 0.2070 0.5194 0.6440 0.035 Uiso 1 1 calc R . .
N5 N 0.77797(11) 0.34905(9) 0.80402(7) 0.01590(19) Uani 1 1 d . . .
N6 N 0.81513(13) 0.41691(11) 0.96672(8) 0.0209(2) Uani 1 1 d . . .
H6A H 0.8534 0.3664 0.9852 0.025 Uiso 1 1 calc R . .
H6B H 0.8063 0.4664 1.0095 0.025 Uiso 1 1 calc R . .
C36 C 0.90221(15) 0.06002(12) 0.85784(10) 0.0231(3) Uani 1 1 d . . .
H36 H 0.9296 -0.0055 0.8684 0.028 Uiso 1 1 calc R . .
C35 C 0.98482(14) 0.16196(12) 0.83079(10) 0.0212(2) Uani 1 1 d . . .
H35 H 1.0687 0.1659 0.8226 0.025 Uiso 1 1 calc R . .
C34 C 0.94519(13) 0.25820(12) 0.81563(9) 0.0181(2) Uani 1 1 d . . .
H34 H 1.0035 0.3277 0.7979 0.022 Uiso 1 1 calc R . .
C33 C 0.82185(13) 0.25513(11) 0.82589(8) 0.0152(2) Uani 1 1 d . . .
C39 C 0.77000(13) 0.41837(11) 0.87304(8) 0.0151(2) Uani 1 1 d . . .
C27 C 0.71553(13) 0.51243(11) 0.84947(9) 0.0153(2) Uani 1 1 d . . .
C28 C 0.76431(14) 0.62497(12) 0.92128(9) 0.0194(2) Uani 1 1 d . . .
H28 H 0.8319 0.6415 0.9861 0.023 Uiso 1 1 calc R . .
C29 C 0.71387(15) 0.71300(13) 0.89793(10) 0.0240(3) Uani 1 1 d . . .
H29 H 0.7466 0.7893 0.9470 0.029 Uiso 1 1 calc R . .
C30 C 0.61617(15) 0.68964(13) 0.80337(10) 0.0233(3) Uani 1 1 d . . .
H30 H 0.5830 0.7505 0.7875 0.028 Uiso 1 1 calc R . .
C37 C 0.77971(15) 0.05457(12) 0.86929(10) 0.0227(3) Uani 1 1 d . . .
H37 H 0.7229 -0.0140 0.8885 0.027 Uiso 1 1 calc R . .
C38 C 0.74156(13) 0.15024(12) 0.85230(9) 0.0185(2) Uani 1 1 d . . .
C32 C 0.61545(13) 0.48861(12) 0.75467(9) 0.0174(2) Uani 1 1 d . . .
H32 H 0.5807 0.4114 0.7057 0.021 Uiso 1 1 calc R . .
C31 C 0.56648(14) 0.57724(12) 0.73158(9) 0.0205(2) Uani 1 1 d . . .
H31 H 0.4991 0.5611 0.6668 0.025 Uiso 1 1 calc R . .
C17 C 0.3884(3) 0.96935(17) 0.58037(16) 0.0527(5) Uani 1 1 d . A .
H17 H 0.4259 1.0591 0.6080 0.063 Uiso 1 1 calc R . .
C18 C 0.2804(3) 0.9068(2) 0.48638(17) 0.0629(7) Uani 1 1 d . . .
H18 H 0.2398 0.9529 0.4500 0.075 Uiso 1 1 calc R . .
C19 C 0.2301(2) 0.77706(17) 0.44417(13) 0.0457(5) Uani 1 1 d . A .
H19 H 0.1550 0.7346 0.3794 0.055 Uiso 1 1 calc R . .
C14 C 0.28936(15) 0.70933(12) 0.49651(9) 0.0210(2) Uani 1 1 d . . .
C26 C 0.23630(14) 0.57016(12) 0.45274(9) 0.0190(2) Uani 1 1 d . A .
C15 C 0.3927(2) 0.77142(16) 0.59118(13) 0.0468(5) Uani 1 1 d . A .
H15 H 0.4320 0.7253 0.6285 0.056 Uiso 1 1 calc R . .
C16 C 0.4409(3) 0.90050(18) 0.63347(16) 0.0642(7) Uani 1 1 d . . .
H16 H 0.5109 0.9414 0.6998 0.077 Uiso 1 1 calc R A .
C10 C 0.18952(16) 0.92115(13) 0.87697(10) 0.0249(3) Uani 1 1 d . . .
H10 H 0.1770 0.9961 0.8816 0.030 Uiso 1 1 calc R . .
C9 C 0.32479(16) 0.93060(13) 0.88850(11) 0.0252(3) Uani 1 1 d . . .
H9 H 0.4063 1.0119 0.9019 0.030 Uiso 1 1 calc R . .
C8 C 0.33905(15) 0.81974(13) 0.88020(10) 0.0223(3) Uani 1 1 d . . .
C7 C 0.22423(14) 0.69782(11) 0.86098(9) 0.0175(2) Uani 1 1 d . . .
C13 C 0.24084(13) 0.53020(12) 0.77918(9) 0.0174(2) Uani 1 1 d . . .
C1 C 0.27036(13) 0.41777(11) 0.77782(9) 0.0168(2) Uani 1 1 d . . .
C6 C 0.35890(14) 0.40880(12) 0.86485(9) 0.0195(2) Uani 1 1 d . . .
H6 H 0.3975 0.4729 0.9247 0.023 Uiso 1 1 calc R . .
C5 C 0.39064(15) 0.30646(13) 0.86423(10) 0.0233(3) Uani 1 1 d . . .
H5 H 0.4511 0.3009 0.9236 0.028 Uiso 1 1 calc R . .
C4 C 0.33438(15) 0.21230(13) 0.77716(11) 0.0252(3) Uani 1 1 d . . .
H4 H 0.3575 0.1431 0.7767 0.030 Uiso 1 1 calc R . .
C11 C 0.07234(15) 0.80176(13) 0.85864(10) 0.0238(3) Uani 1 1 d . . .
H11 H -0.0203 0.7952 0.8512 0.029 Uiso 1 1 calc R . .
C12 C 0.08993(14) 0.69179(12) 0.85119(9) 0.0196(2) Uani 1 1 d . . .
H12 H 0.0089 0.6108 0.8392 0.024 Uiso 1 1 calc R . .
C3 C 0.24426(16) 0.21946(13) 0.69077(10) 0.0251(3) Uani 1 1 d . . .
H3 H 0.2046 0.1544 0.6312 0.030 Uiso 1 1 calc R . .
C2 C 0.21178(15) 0.32136(12) 0.69102(9) 0.0214(2) Uani 1 1 d . . .
H2 H 0.1493 0.3253 0.6317 0.026 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2A C21A 1.239(2) . ?
C20A C25A 1.380(3) . ?
C20A C21A 1.382(3) . ?
C20A N3 1.4213(17) . ?
C21A C22A 1.385(2) . ?
C22A C23A 1.371(3) . ?
C22A H22A 0.9500 . ?
C23A C24A 1.377(3) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.389(2) . ?
C24A H24A 0.9500 . ?
C25A H25A 0.9500 . ?
F3 C38 1.3591(14) . ?
F1 C8 1.3559(15) . ?
N3 C26 1.2955(16) . ?
N4 C26 1.3449(16) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N1 C13 1.2949(16) . ?
N1 C7 1.4168(15) . ?
N2 C13 1.3450(16) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N5 C39 1.3038(15) . ?
N5 C33 1.4103(15) . ?
N6 C39 1.3457(15) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
C36 C37 1.3852(19) . ?
C36 C35 1.3897(19) . ?
C36 H36 0.9500 . ?
C35 C34 1.3906(17) . ?
C35 H35 0.9500 . ?
C34 C33 1.3959(17) . ?
C34 H34 0.9500 . ?
C33 C38 1.3969(16) . ?
C39 C27 1.4869(16) . ?
C27 C28 1.3945(17) . ?
C27 C32 1.3949(16) . ?
C28 C29 1.3918(18) . ?
C28 H28 0.9500 . ?
C29 C30 1.3844(19) . ?
C29 H29 0.9500 . ?
C30 C31 1.3906(18) . ?
C30 H30 0.9500 . ?
C37 C38 1.3795(17) . ?
C37 H37 0.9500 . ?
C32 C31 1.3879(17) . ?
C32 H32 0.9500 . ?
C31 H31 0.9500 . ?
C17 C16 1.366(3) . ?
C17 C18 1.375(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C14 1.385(2) . ?
C19 H19 0.9500 . ?
C14 C15 1.368(2) . ?
C14 C26 1.4858(17) . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C10 C9 1.385(2) . ?
C10 C11 1.3872(19) . ?
C10 H10 0.9500 . ?
C9 C8 1.3801(18) . ?
C9 H9 0.9500 . ?
C8 C7 1.3921(18) . ?
C7 C12 1.3963(18) . ?
C13 C1 1.4912(17) . ?
C1 C2 1.3932(17) . ?
C1 C6 1.3970(17) . ?
C6 C5 1.3891(18) . ?
C6 H6 0.9500 . ?
C5 C4 1.387(2) . ?
C5 H5 0.9500 . ?
C4 C3 1.387(2) . ?
C4 H4 0.9500 . ?
C11 C12 1.3889(18) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C3 C2 1.3891(18) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?

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
C25A C20A C21A 116.34(15) . . ?
C25A C20A N3 122.26(16) . . ?
C21A C20A N3 121.33(16) . . ?
F2A C21A C20A 115.82(16) . . ?
F2A C21A C22A 120.7(2) . . ?
C20A C21A C22A 123.32(19) . . ?
C23A C22A C21A 118.8(2) . . ?
C23A C22A H22A 120.6 . . ?
C21A C22A H22A 120.6 . . ?
C22A C23A C24A 119.76(16) . . ?
C22A C23A H23A 120.1 . . ?
C24A C23A H23A 120.1 . . ?
C23A C24A C25A 120.2(2) . . ?
C23A C24A H24A 119.9 . . ?
C25A C24A H24A 119.9 . . ?
C20A C25A C24A 121.6(2) . . ?
C20A C25A H25A 119.2 . . ?
C24A C25A H25A 119.2 . . ?
C26 N3 C20A 116.55(11) . . ?
C26 N4 H4A 120.0 . . ?
C26 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C13 N1 C7 117.61(10) . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C39 N5 C33 117.86(10) . . ?
C39 N6 H6A 120.0 . . ?
C39 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C37 C36 C35 119.58(12) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C36 C35 C34 120.26(12) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C34 C33 121.59(11) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C34 C33 C38 116.06(11) . . ?
C34 C33 N5 120.70(10) . . ?
C38 C33 N5 123.10(11) . . ?
N5 C39 N6 124.95(11) . . ?
N5 C39 C27 118.49(10) . . ?
N6 C39 C27 116.45(10) . . ?
C28 C27 C32 119.57(11) . . ?
C28 C27 C39 120.56(11) . . ?
C32 C27 C39 119.88(10) . . ?
C29 C28 C27 119.97(12) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C30 C29 C28 120.17(12) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 120.12(12) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C38 C37 C36 118.95(12) . . ?
C38 C37 H37 120.5 . . ?
C36 C37 H37 120.5 . . ?
F3 C38 C37 118.21(11) . . ?
F3 C38 C33 118.25(11) . . ?
C37 C38 C33 123.54(11) . . ?
C31 C32 C27 120.23(11) . . ?
C31 C32 H32 119.9 . . ?
C27 C32 H32 119.9 . . ?
C32 C31 C30 119.94(12) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C16 C17 C18 119.05(16) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C19 120.69(18) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 120.01(17) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C15 C14 C19 118.69(14) . . ?
C15 C14 C26 120.45(12) . . ?
C19 C14 C26 120.78(13) . . ?
N3 C26 N4 124.46(12) . . ?
N3 C26 C14 118.91(11) . . ?
N4 C26 C14 116.62(11) . . ?
C14 C15 C16 121.01(16) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 120.40(18) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C9 C10 C11 119.74(12) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C8 C9 C10 118.79(12) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
F1 C8 C9 118.55(12) . . ?
F1 C8 C7 117.99(11) . . ?
C9 C8 C7 123.46(12) . . ?
C8 C7 C12 116.36(11) . . ?
C8 C7 N1 121.73(11) . . ?
C12 C7 N1 121.72(11) . . ?
N1 C13 N2 124.93(12) . . ?
N1 C13 C1 118.18(11) . . ?
N2 C13 C1 116.89(11) . . ?
C2 C1 C6 119.16(11) . . ?
C2 C1 C13 121.19(11) . . ?
C6 C1 C13 119.65(11) . . ?
C5 C6 C1 120.25(12) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C4 C5 C6 120.21(12) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C3 C4 C5 119.80(12) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C10 C11 C12 120.29(12) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 121.36(12) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C4 C3 C2 120.22(12) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C2 C1 120.33(12) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?

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
C25A C20A C21A F2A -175.04(16) . . . . ?
N3 C20A C21A F2A 7.9(2) . . . . ?
C25A C20A C21A C22A 0.3(2) . . . . ?
N3 C20A C21A C22A -176.79(14) . . . . ?
F2A C21A C22A C23A 174.15(17) . . . . ?
C20A C21A C22A C23A -1.0(3) . . . . ?
C21A C22A C23A C24A 0.6(3) . . . . ?
C22A C23A C24A C25A 0.5(3) . . . . ?
C21A C20A C25A C24A 0.8(2) . . . . ?
N3 C20A C25A C24A 177.82(15) . . . . ?
C23A C24A C25A C20A -1.2(3) . . . . ?
C25A C20A N3 C26 96.61(18) . . . . ?
C21A C20A N3 C26 -86.49(18) . . . . ?
C37 C36 C35 C34 0.2(2) . . . . ?
C36 C35 C34 C33 -0.68(19) . . . . ?
C35 C34 C33 C38 0.10(18) . . . . ?
C35 C34 C33 N5 -175.84(11) . . . . ?
C39 N5 C33 C34 -122.05(13) . . . . ?
C39 N5 C33 C38 62.30(16) . . . . ?
C33 N5 C39 N6 7.35(18) . . . . ?
C33 N5 C39 C27 -176.48(10) . . . . ?
N5 C39 C27 C28 -150.39(12) . . . . ?
N6 C39 C27 C28 26.10(16) . . . . ?
N5 C39 C27 C32 29.22(16) . . . . ?
N6 C39 C27 C32 -154.29(11) . . . . ?
C32 C27 C28 C29 -0.43(18) . . . . ?
C39 C27 C28 C29 179.18(11) . . . . ?
C27 C28 C29 C30 -0.5(2) . . . . ?
C28 C29 C30 C31 0.9(2) . . . . ?
C35 C36 C37 C38 0.8(2) . . . . ?
C36 C37 C38 F3 177.90(12) . . . . ?
C36 C37 C38 C33 -1.4(2) . . . . ?
C34 C33 C38 F3 -178.35(11) . . . . ?
N5 C33 C38 F3 -2.52(18) . . . . ?
C34 C33 C38 C37 0.96(18) . . . . ?
N5 C33 C38 C37 176.79(12) . . . . ?
C28 C27 C32 C31 0.98(18) . . . . ?
C39 C27 C32 C31 -178.63(11) . . . . ?
C27 C32 C31 C30 -0.61(19) . . . . ?
C29 C30 C31 C32 -0.3(2) . . . . ?
C16 C17 C18 C19 -3.0(4) . . . . ?
C17 C18 C19 C14 -0.4(4) . . . . ?
C18 C19 C14 C15 2.9(3) . . . . ?
C18 C19 C14 C26 179.65(19) . . . . ?
C20A N3 C26 N4 1.2(2) . . . . ?
C20A N3 C26 C14 -179.39(13) . . . . ?
C15 C14 C26 N3 26.2(2) . . . . ?
C19 C14 C26 N3 -150.48(16) . . . . ?
C15 C14 C26 N4 -154.35(16) . . . . ?
C19 C14 C26 N4 28.9(2) . . . . ?
C19 C14 C15 C16 -1.9(3) . . . . ?
C26 C14 C15 C16 -178.7(2) . . . . ?
C18 C17 C16 C15 4.0(4) . . . . ?
C14 C15 C16 C17 -1.6(4) . . . . ?
C11 C10 C9 C8 0.8(2) . . . . ?
C10 C9 C8 F1 -179.66(13) . . . . ?
C10 C9 C8 C7 -0.2(2) . . . . ?
F1 C8 C7 C12 178.74(11) . . . . ?
C9 C8 C7 C12 -0.74(19) . . . . ?
F1 C8 C7 N1 3.61(18) . . . . ?
C9 C8 C7 N1 -175.87(12) . . . . ?
C13 N1 C7 C8 -83.16(16) . . . . ?
C13 N1 C7 C12 101.97(14) . . . . ?
C7 N1 C13 N2 -4.11(19) . . . . ?
C7 N1 C13 C1 177.16(10) . . . . ?
N1 C13 C1 C2 153.61(12) . . . . ?
N2 C13 C1 C2 -25.23(18) . . . . ?
N1 C13 C1 C6 -26.72(17) . . . . ?
N2 C13 C1 C6 154.44(12) . . . . ?
C2 C1 C6 C5 1.46(18) . . . . ?
C13 C1 C6 C5 -178.21(11) . . . . ?
C1 C6 C5 C4 -0.12(19) . . . . ?
C6 C5 C4 C3 -1.0(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C7 -0.5(2) . . . . ?
C8 C7 C12 C11 1.10(18) . . . . ?
N1 C7 C12 C11 176.23(11) . . . . ?
C5 C4 C3 C2 0.8(2) . . . . ?
C4 C3 C2 C1 0.5(2) . . . . ?
C6 C1 C2 C3 -1.67(19) . . . . ?
C13 C1 C2 C3 178.00(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.63
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.054
