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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_252
_database_code_depnum_ccdc_archive 'CCDC 1438186'
_audit_update_record             
;
2015-11-22 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 F4 N2 O2'
_chemical_formula_sum            'C20 H14 F4 N2 O2'
_chemical_formula_weight         390.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   11.228(2)
_cell_length_b                   12.460(3)
_cell_length_c                   12.943(3)
_cell_angle_alpha                77.35(3)
_cell_angle_beta                 89.67(3)
_cell_angle_gamma                86.39(3)
_cell_volume                     1763.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8224
_cell_measurement_theta_min      3.94
_cell_measurement_theta_max      66.89

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6007
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11932
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.94
_diffrn_reflns_theta_max         65.98
_reflns_number_total             5661
_reflns_number_gt                5266
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0888P)²+0.3570P] 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       0.0029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5661
_refine_ls_number_parameters     506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1449
_refine_ls_wR_factor_gt          0.1424
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.09501(9) 0.38676(9) 0.97798(9) 0.0571(3) Uani 1 1 d . . .
F2 F -0.01400(10) 0.25503(11) 0.88500(12) 0.0745(4) Uani 1 1 d . . .
F3 F 0.08376(13) 0.21662(13) 0.75394(12) 0.0863(4) Uani 1 1 d . . .
F4 F 0.06504(12) 0.38326(11) 0.77195(10) 0.0737(4) Uani 1 1 d . . .
F5 F 0.18154(12) 0.67261(13) 0.44497(11) 0.0826(4) Uani 1 1 d . . .
F6 F 0.10765(12) 0.83574(14) 0.43583(11) 0.0895(5) Uani 1 1 d . . .
F7 F 0.26414(14) 0.80957(15) 0.34725(9) 0.0898(5) Uani 1 1 d . . .
F8 F 0.41511(11) 0.66008(12) 0.46737(10) 0.0755(4) Uani 1 1 d . . .
O1 O 0.33157(14) 0.35452(13) 0.75424(11) 0.0657(4) Uani 1 1 d . . .
O2 O 0.45763(11) 0.24241(11) 0.97015(11) 0.0599(4) Uani 1 1 d . . .
O3 O 0.44275(13) 0.86874(12) 0.69439(10) 0.0618(4) Uani 1 1 d . . .
O4 O 0.34303(16) 0.97663(14) 0.46278(13) 0.0801(5) Uani 1 1 d . . .
N1 N 0.48560(12) 0.36105(12) 1.07859(11) 0.0482(3) Uani 1 1 d . . .
N2 N 0.35010(14) 0.16485(14) 0.81086(13) 0.0576(4) Uani 1 1 d . . .
N3 N 0.63892(14) 0.80603(14) 0.68699(12) 0.0558(4) Uani 1 1 d . . .
N4 N 0.21290(15) 0.93915(14) 0.60209(13) 0.0593(4) Uani 1 1 d . . .
C1 C 0.20930(18) 0.50058(17) 1.13016(15) 0.0579(5) Uani 1 1 d . . .
H1A H 0.1299 0.5027 1.1092 0.069 Uiso 1 1 calc R . .
C2 C 0.2439(2) 0.56305(19) 1.20028(18) 0.0700(6) Uani 1 1 d . . .
H2A H 0.1868 0.6071 1.2268 0.084 Uiso 1 1 calc R . .
C3 C 0.3606(2) 0.56089(19) 1.23103(17) 0.0698(6) Uani 1 1 d . . .
H3A H 0.3812 0.6041 1.2775 0.084 Uiso 1 1 calc R . .
C4 C 0.44903(19) 0.49578(17) 1.19456(15) 0.0589(5) Uani 1 1 d . . .
H4A H 0.5282 0.4944 1.2157 0.071 Uiso 1 1 calc R . .
C5 C 0.41423(15) 0.43344(14) 1.12575(13) 0.0463(4) Uani 1 1 d . . .
C6 C 0.41952(15) 0.31246(14) 1.01631(13) 0.0460(4) Uani 1 1 d . . .
C7 C 0.29373(14) 0.36042(13) 1.01906(13) 0.0438(4) Uani 1 1 d . . .
C8 C 0.29557(15) 0.43504(14) 1.09209(13) 0.0451(4) Uani 1 1 d . . .
C9 C 0.20292(14) 0.33685(13) 0.96437(13) 0.0441(4) Uani 1 1 d . . .
C10 C 0.19811(15) 0.25776(14) 0.89091(14) 0.0474(4) Uani 1 1 d . . .
C11 C 0.30336(16) 0.26919(16) 0.80954(14) 0.0517(4) Uani 1 1 d . . .
C12 C 0.30457(16) 0.08832(16) 0.89478(16) 0.0550(4) Uani 1 1 d . . .
C13 C 0.3401(2) -0.02179(19) 0.9296(2) 0.0735(6) Uani 1 1 d . . .
H13A H 0.4011 -0.0548 0.8961 0.088 Uiso 1 1 calc R . .
C14 C 0.2822(2) -0.08132(19) 1.0157(2) 0.0816(7) Uani 1 1 d . . .
H14A H 0.3055 -0.1554 1.0410 0.098 Uiso 1 1 calc R . .
C15 C 0.1901(2) -0.03349(19) 1.0655(2) 0.0752(6) Uani 1 1 d . . .
H15A H 0.1517 -0.0757 1.1227 0.090 Uiso 1 1 calc R . .
C16 C 0.15490(18) 0.07775(17) 1.02981(17) 0.0602(5) Uani 1 1 d . . .
H16A H 0.0932 0.1107 1.0625 0.072 Uiso 1 1 calc R . .
C17 C 0.21345(15) 0.13731(14) 0.94552(14) 0.0493(4) Uani 1 1 d . . .
C18 C 0.61240(16) 0.33726(18) 1.09583(16) 0.0577(5) Uani 1 1 d . . .
H18A H 0.6408 0.2853 1.0550 0.087 Uiso 1 1 calc R . .
H18B H 0.6278 0.3066 1.1696 0.087 Uiso 1 1 calc R . .
H18C H 0.6529 0.4040 1.0743 0.087 Uiso 1 1 calc R . .
C19 C 0.4583(2) 0.1455(2) 0.7536(2) 0.0806(7) Uani 1 1 d . . .
H19A H 0.4713 0.2097 0.6993 0.121 Uiso 1 1 calc R . .
H19B H 0.4502 0.0835 0.7220 0.121 Uiso 1 1 calc R . .
H19C H 0.5250 0.1306 0.8018 0.121 Uiso 1 1 calc R . .
C20 C 0.08229(17) 0.27957(17) 0.82476(17) 0.0598(5) Uani 1 1 d . . .
C21 C 0.6781(2) 0.6321(2) 0.50050(17) 0.0675(5) Uani 1 1 d . . .
H21A H 0.6290 0.6041 0.4565 0.081 Uiso 1 1 calc R . .
C22 C 0.8007(2) 0.6076(2) 0.5031(2) 0.0805(7) Uani 1 1 d . . .
H22A H 0.8339 0.5630 0.4601 0.097 Uiso 1 1 calc R . .
C23 C 0.8735(2) 0.6482(3) 0.5683(2) 0.0846(7) Uani 1 1 d . . .
H23A H 0.9552 0.6305 0.5688 0.102 Uiso 1 1 calc R . .
C24 C 0.8275(2) 0.7154(2) 0.63352(19) 0.0730(6) Uani 1 1 d . . .
H24A H 0.8770 0.7430 0.6775 0.088 Uiso 1 1 calc R . .
C25 C 0.70621(17) 0.73972(17) 0.63070(14) 0.0557(4) Uani 1 1 d . . .
C26 C 0.52176(17) 0.81618(15) 0.65849(13) 0.0510(4) Uani 1 1 d . . .
C27 C 0.51034(16) 0.74581(16) 0.57884(13) 0.0503(4) Uani 1 1 d . . .
C28 C 0.63061(16) 0.69910(16) 0.56489(14) 0.0534(4) Uani 1 1 d . . .
C29 C 0.40928(16) 0.73235(16) 0.53149(14) 0.0517(4) Uani 1 1 d . . .
C30 C 0.28609(16) 0.78707(16) 0.53483(14) 0.0510(4) Uani 1 1 d . . .
C31 C 0.28855(18) 0.91447(17) 0.52714(15) 0.0578(5) Uani 1 1 d . . .
C32 C 0.17679(16) 0.84478(16) 0.67052(14) 0.0527(4) Uani 1 1 d . . .
C33 C 0.11240(18) 0.8376(2) 0.76287(17) 0.0656(5) Uani 1 1 d . . .
H33A H 0.0863 0.9004 0.7863 0.079 Uiso 1 1 calc R . .
C34 C 0.08826(19) 0.7341(2) 0.81885(18) 0.0731(6) Uani 1 1 d . . .
H34A H 0.0452 0.7274 0.8813 0.088 Uiso 1 1 calc R . .
C35 C 0.12572(18) 0.6411(2) 0.78535(17) 0.0680(6) Uani 1 1 d . . .
H35A H 0.1070 0.5724 0.8246 0.082 Uiso 1 1 calc R . .
C36 C 0.19210(17) 0.64819(17) 0.69250(16) 0.0573(5) Uani 1 1 d . . .
H36A H 0.2186 0.5851 0.6696 0.069 Uiso 1 1 calc R . .
C37 C 0.21681(15) 0.75087(15) 0.63633(13) 0.0490(4) Uani 1 1 d . . .
C38 C 0.6884(2) 0.8670(2) 0.75793(17) 0.0711(6) Uani 1 1 d . . .
H38A H 0.6249 0.9059 0.7874 0.107 Uiso 1 1 calc R . .
H38B H 0.7413 0.9189 0.7195 0.107 Uiso 1 1 calc R . .
H38C H 0.7318 0.8169 0.8140 0.107 Uiso 1 1 calc R . .
C39 C 0.1952(3) 1.05006(19) 0.6205(2) 0.0822(7) Uani 1 1 d . . .
H39A H 0.2280 1.1014 0.5627 0.123 Uiso 1 1 calc R . .
H39B H 0.2345 1.0536 0.6852 0.123 Uiso 1 1 calc R . .
H39C H 0.1113 1.0684 0.6257 0.123 Uiso 1 1 calc R . .
C40 C 0.20997(19) 0.7756(2) 0.43970(16) 0.0659(5) 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
F1 C9 1.3552(19) . ?
F2 C20 1.341(3) . ?
F3 C20 1.330(2) . ?
F4 C20 1.326(2) . ?
F5 C40 1.329(3) . ?
F6 C40 1.327(3) . ?
F7 C40 1.335(3) . ?
F8 C29 1.350(2) . ?
O1 C11 1.204(2) . ?
O2 C6 1.217(2) . ?
O3 C26 1.220(2) . ?
O4 C31 1.200(3) . ?
N1 C6 1.358(2) . ?
N1 C5 1.405(2) . ?
N1 C18 1.444(2) . ?
N2 C11 1.368(3) . ?
N2 C12 1.397(3) . ?
N2 C19 1.454(3) . ?
N3 C26 1.359(2) . ?
N3 C25 1.401(3) . ?
N3 C38 1.447(3) . ?
N4 C31 1.358(3) . ?
N4 C32 1.390(3) . ?
N4 C39 1.454(3) . ?
C1 C8 1.385(3) . ?
C1 C2 1.390(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.369(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.389(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4A 0.9300 . ?
C5 C8 1.402(2) . ?
C6 C7 1.502(2) . ?
C7 C9 1.328(2) . ?
C7 C8 1.465(2) . ?
C9 C10 1.515(2) . ?
C10 C17 1.512(3) . ?
C10 C20 1.538(2) . ?
C10 C11 1.571(2) . ?
C12 C13 1.381(3) . ?
C12 C17 1.393(3) . ?
C13 C14 1.380(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.387(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.394(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.368(3) . ?
C16 H16A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C28 1.386(3) . ?
C21 C22 1.391(3) . ?
C21 H21A 0.9300 . ?
C22 C23 1.372(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.389(4) . ?
C23 H23A 0.9300 . ?
C24 C25 1.375(3) . ?
C24 H24A 0.9300 . ?
C25 C28 1.398(3) . ?
C26 C27 1.503(3) . ?
C27 C29 1.330(3) . ?
C27 C28 1.463(3) . ?
C29 C30 1.508(3) . ?
C30 C37 1.519(2) . ?
C30 C40 1.540(3) . ?
C30 C31 1.571(3) . ?
C32 C33 1.382(3) . ?
C32 C37 1.387(3) . ?
C33 C34 1.376(4) . ?
C33 H33A 0.9300 . ?
C34 C35 1.366(4) . ?
C34 H34A 0.9300 . ?
C35 C36 1.400(3) . ?
C35 H35A 0.9300 . ?
C36 C37 1.370(3) . ?
C36 H36A 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C5 111.34(14) . . ?
C6 N1 C18 123.48(15) . . ?
C5 N1 C18 125.15(15) . . ?
C11 N2 C12 111.19(15) . . ?
C11 N2 C19 121.49(19) . . ?
C12 N2 C19 124.62(19) . . ?
C26 N3 C25 111.72(16) . . ?
C26 N3 C38 123.17(18) . . ?
C25 N3 C38 124.75(18) . . ?
C31 N4 C32 111.77(16) . . ?
C31 N4 C39 122.3(2) . . ?
C32 N4 C39 124.64(19) . . ?
C8 C1 C2 118.59(19) . . ?
C8 C1 H1A 120.7 . . ?
C2 C1 H1A 120.7 . . ?
C3 C2 C1 121.11(19) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
C2 C3 C4 121.66(19) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C5 C4 C3 117.03(19) . . ?
C5 C4 H4A 121.5 . . ?
C3 C4 H4A 121.5 . . ?
C4 C5 C8 122.47(17) . . ?
C4 C5 N1 128.04(17) . . ?
C8 C5 N1 109.50(15) . . ?
O2 C6 N1 125.13(15) . . ?
O2 C6 C7 128.35(16) . . ?
N1 C6 C7 106.51(14) . . ?
C9 C7 C8 129.35(15) . . ?
C9 C7 C6 124.77(15) . . ?
C8 C7 C6 105.87(14) . . ?
C1 C8 C5 119.14(16) . . ?
C1 C8 C7 134.15(17) . . ?
C5 C8 C7 106.71(14) . . ?
C7 C9 F1 116.63(14) . . ?
C7 C9 C10 130.29(15) . . ?
F1 C9 C10 113.02(14) . . ?
C17 C10 C9 114.52(14) . . ?
C17 C10 C20 109.96(15) . . ?
C9 C10 C20 110.91(14) . . ?
C17 C10 C11 101.98(14) . . ?
C9 C10 C11 112.61(14) . . ?
C20 C10 C11 106.24(15) . . ?
O1 C11 N2 127.98(18) . . ?
O1 C11 C10 125.09(17) . . ?
N2 C11 C10 106.84(16) . . ?
C13 C12 C17 120.8(2) . . ?
C13 C12 N2 128.28(18) . . ?
C17 C12 N2 110.95(16) . . ?
C14 C13 C12 117.9(2) . . ?
C14 C13 H13A 121.1 . . ?
C12 C13 H13A 121.1 . . ?
C13 C14 C15 121.6(2) . . ?
C13 C14 H14A 119.2 . . ?
C15 C14 H14A 119.2 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C17 C16 C15 118.38(19) . . ?
C17 C16 H16A 120.8 . . ?
C15 C16 H16A 120.8 . . ?
C16 C17 C12 121.25(17) . . ?
C16 C17 C10 130.77(16) . . ?
C12 C17 C10 107.97(16) . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F4 C20 F3 107.15(17) . . ?
F4 C20 F2 107.45(16) . . ?
F3 C20 F2 106.50(17) . . ?
F4 C20 C10 113.18(16) . . ?
F3 C20 C10 110.43(16) . . ?
F2 C20 C10 111.79(17) . . ?
C28 C21 C22 118.5(2) . . ?
C28 C21 H21A 120.7 . . ?
C22 C21 H21A 120.7 . . ?
C23 C22 C21 121.0(2) . . ?
C23 C22 H22A 119.5 . . ?
C21 C22 H22A 119.5 . . ?
C22 C23 C24 121.3(2) . . ?
C22 C23 H23A 119.3 . . ?
C24 C23 H23A 119.3 . . ?
C25 C24 C23 117.7(2) . . ?
C25 C24 H24A 121.2 . . ?
C23 C24 H24A 121.2 . . ?
C24 C25 C28 121.9(2) . . ?
C24 C25 N3 128.6(2) . . ?
C28 C25 N3 109.46(16) . . ?
O3 C26 N3 126.06(17) . . ?
O3 C26 C27 127.97(17) . . ?
N3 C26 C27 105.91(16) . . ?
C29 C27 C28 128.68(17) . . ?
C29 C27 C26 125.16(17) . . ?
C28 C27 C26 106.15(15) . . ?
C21 C28 C25 119.63(18) . . ?
C21 C28 C27 133.62(18) . . ?
C25 C28 C27 106.69(17) . . ?
C27 C29 F8 116.65(16) . . ?
C27 C29 C30 130.65(16) . . ?
F8 C29 C30 112.68(15) . . ?
C29 C30 C37 116.24(15) . . ?
C29 C30 C40 110.99(15) . . ?
C37 C30 C40 109.41(15) . . ?
C29 C30 C31 112.43(15) . . ?
C37 C30 C31 101.59(15) . . ?
C40 C30 C31 105.30(16) . . ?
O4 C31 N4 128.0(2) . . ?
O4 C31 C30 125.15(19) . . ?
N4 C31 C30 106.75(16) . . ?
C33 C32 C37 121.1(2) . . ?
C33 C32 N4 127.95(19) . . ?
C37 C32 N4 110.93(16) . . ?
C34 C33 C32 117.6(2) . . ?
C34 C33 H33A 121.2 . . ?
C32 C33 H33A 121.2 . . ?
C35 C34 C33 121.9(2) . . ?
C35 C34 H34A 119.1 . . ?
C33 C34 H34A 119.1 . . ?
C34 C35 C36 120.5(2) . . ?
C34 C35 H35A 119.7 . . ?
C36 C35 H35A 119.7 . . ?
C37 C36 C35 118.0(2) . . ?
C37 C36 H36A 121.0 . . ?
C35 C36 H36A 121.0 . . ?
C36 C37 C32 120.86(17) . . ?
C36 C37 C30 131.28(17) . . ?
C32 C37 C30 107.85(16) . . ?
N3 C38 H38A 109.5 . . ?
N3 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N3 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N4 C39 H39A 109.5 . . ?
N4 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
N4 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
F6 C40 F5 106.33(19) . . ?
F6 C40 F7 106.97(18) . . ?
F5 C40 F7 107.43(18) . . ?
F6 C40 C30 110.47(17) . . ?
F5 C40 C30 112.70(18) . . ?
F7 C40 C30 112.58(18) . . ?

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
C8 C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C8 0.6(3) . . . . ?
C3 C4 C5 N1 -179.56(19) . . . . ?
C6 N1 C5 C4 178.99(18) . . . . ?
C18 N1 C5 C4 1.0(3) . . . . ?
C6 N1 C5 C8 -1.2(2) . . . . ?
C18 N1 C5 C8 -179.18(16) . . . . ?
C5 N1 C6 O2 -176.32(17) . . . . ?
C18 N1 C6 O2 1.7(3) . . . . ?
C5 N1 C6 C7 2.41(19) . . . . ?
C18 N1 C6 C7 -179.53(15) . . . . ?
O2 C6 C7 C9 -4.1(3) . . . . ?
N1 C6 C7 C9 177.18(16) . . . . ?
O2 C6 C7 C8 175.95(18) . . . . ?
N1 C6 C7 C8 -2.73(18) . . . . ?
C2 C1 C8 C5 0.3(3) . . . . ?
C2 C1 C8 C7 -179.69(19) . . . . ?
C4 C5 C8 C1 -0.8(3) . . . . ?
N1 C5 C8 C1 179.32(16) . . . . ?
C4 C5 C8 C7 179.19(16) . . . . ?
N1 C5 C8 C7 -0.68(19) . . . . ?
C9 C7 C8 C1 2.2(3) . . . . ?
C6 C7 C8 C1 -177.9(2) . . . . ?
C9 C7 C8 C5 -177.85(17) . . . . ?
C6 C7 C8 C5 2.05(18) . . . . ?
C8 C7 C9 F1 -1.1(3) . . . . ?
C6 C7 C9 F1 178.99(14) . . . . ?
C8 C7 C9 C10 -178.06(17) . . . . ?
C6 C7 C9 C10 2.1(3) . . . . ?
C7 C9 C10 C17 69.0(2) . . . . ?
F1 C9 C10 C17 -108.00(16) . . . . ?
C7 C9 C10 C20 -165.80(18) . . . . ?
F1 C9 C10 C20 17.2(2) . . . . ?
C7 C9 C10 C11 -46.9(3) . . . . ?
F1 C9 C10 C11 136.08(15) . . . . ?
C12 N2 C11 O1 172.60(18) . . . . ?
C19 N2 C11 O1 10.4(3) . . . . ?
C12 N2 C11 C10 -10.58(19) . . . . ?
C19 N2 C11 C10 -172.77(18) . . . . ?
C17 C10 C11 O1 -173.59(17) . . . . ?
C9 C10 C11 O1 -50.4(2) . . . . ?
C20 C10 C11 O1 71.2(2) . . . . ?
C17 C10 C11 N2 9.48(17) . . . . ?
C9 C10 C11 N2 132.71(15) . . . . ?
C20 C10 C11 N2 -105.69(17) . . . . ?
C11 N2 C12 C13 -171.7(2) . . . . ?
C19 N2 C12 C13 -10.1(3) . . . . ?
C11 N2 C12 C17 7.5(2) . . . . ?
C19 N2 C12 C17 169.00(18) . . . . ?
C17 C12 C13 C14 0.2(3) . . . . ?
N2 C12 C13 C14 179.3(2) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C12 1.2(3) . . . . ?
C15 C16 C17 C10 -178.56(19) . . . . ?
C13 C12 C17 C16 -1.3(3) . . . . ?
N2 C12 C17 C16 179.52(17) . . . . ?
C13 C12 C17 C10 178.53(18) . . . . ?
N2 C12 C17 C10 -0.7(2) . . . . ?
C9 C10 C17 C16 52.6(3) . . . . ?
C20 C10 C17 C16 -73.0(2) . . . . ?
C11 C10 C17 C16 174.56(19) . . . . ?
C9 C10 C17 C12 -127.14(16) . . . . ?
C20 C10 C17 C12 107.19(17) . . . . ?
C11 C10 C17 C12 -5.21(18) . . . . ?
C17 C10 C20 F4 -178.04(15) . . . . ?
C9 C10 C20 F4 54.3(2) . . . . ?
C11 C10 C20 F4 -68.4(2) . . . . ?
C17 C10 C20 F3 -57.9(2) . . . . ?
C9 C10 C20 F3 174.38(16) . . . . ?
C11 C10 C20 F3 51.7(2) . . . . ?
C17 C10 C20 F2 60.5(2) . . . . ?
C9 C10 C20 F2 -67.2(2) . . . . ?
C11 C10 C20 F2 170.08(15) . . . . ?
C28 C21 C22 C23 0.3(4) . . . . ?
C21 C22 C23 C24 -0.3(4) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C23 C24 C25 C28 -0.1(3) . . . . ?
C23 C24 C25 N3 -179.0(2) . . . . ?
C26 N3 C25 C24 176.19(19) . . . . ?
C38 N3 C25 C24 2.9(3) . . . . ?
C26 N3 C25 C28 -2.8(2) . . . . ?
C38 N3 C25 C28 -176.17(17) . . . . ?
C25 N3 C26 O3 179.92(17) . . . . ?
C38 N3 C26 O3 -6.6(3) . . . . ?
C25 N3 C26 C27 2.48(19) . . . . ?
C38 N3 C26 C27 175.93(17) . . . . ?
O3 C26 C27 C29 2.2(3) . . . . ?
N3 C26 C27 C29 179.54(17) . . . . ?
O3 C26 C27 C28 -178.63(18) . . . . ?
N3 C26 C27 C28 -1.26(18) . . . . ?
C22 C21 C28 C25 -0.3(3) . . . . ?
C22 C21 C28 C27 176.3(2) . . . . ?
C24 C25 C28 C21 0.2(3) . . . . ?
N3 C25 C28 C21 179.30(17) . . . . ?
C24 C25 C28 C27 -177.24(18) . . . . ?
N3 C25 C28 C27 1.9(2) . . . . ?
C29 C27 C28 C21 1.9(3) . . . . ?
C26 C27 C28 C21 -177.3(2) . . . . ?
C29 C27 C28 C25 178.79(19) . . . . ?
C26 C27 C28 C25 -0.38(19) . . . . ?
C28 C27 C29 F8 5.3(3) . . . . ?
C26 C27 C29 F8 -175.73(16) . . . . ?
C28 C27 C29 C30 -173.11(18) . . . . ?
C26 C27 C29 C30 5.9(3) . . . . ?
C27 C29 C30 C37 -73.9(3) . . . . ?
F8 C29 C30 C37 107.70(18) . . . . ?
C27 C29 C30 C40 160.2(2) . . . . ?
F8 C29 C30 C40 -18.2(2) . . . . ?
C27 C29 C30 C31 42.6(3) . . . . ?
F8 C29 C30 C31 -135.81(16) . . . . ?
C32 N4 C31 O4 -173.0(2) . . . . ?
C39 N4 C31 O4 -5.6(3) . . . . ?
C32 N4 C31 C30 10.6(2) . . . . ?
C39 N4 C31 C30 178.00(19) . . . . ?
C29 C30 C31 O4 48.7(3) . . . . ?
C37 C30 C31 O4 173.6(2) . . . . ?
C40 C30 C31 O4 -72.3(2) . . . . ?
C29 C30 C31 N4 -134.82(16) . . . . ?
C37 C30 C31 N4 -9.87(18) . . . . ?
C40 C30 C31 N4 104.21(17) . . . . ?
C31 N4 C32 C33 171.53(19) . . . . ?
C39 N4 C32 C33 4.5(3) . . . . ?
C31 N4 C32 C37 -6.9(2) . . . . ?
C39 N4 C32 C37 -174.0(2) . . . . ?
C37 C32 C33 C34 -0.8(3) . . . . ?
N4 C32 C33 C34 -179.1(2) . . . . ?
C32 C33 C34 C35 -0.1(3) . . . . ?
C33 C34 C35 C36 0.9(3) . . . . ?
C34 C35 C36 C37 -0.7(3) . . . . ?
C35 C36 C37 C32 -0.2(3) . . . . ?
C35 C36 C37 C30 179.44(18) . . . . ?
C33 C32 C37 C36 0.9(3) . . . . ?
N4 C32 C37 C36 179.54(16) . . . . ?
C33 C32 C37 C30 -178.77(17) . . . . ?
N4 C32 C37 C30 -0.2(2) . . . . ?
C29 C30 C37 C36 -51.4(3) . . . . ?
C40 C30 C37 C36 75.3(2) . . . . ?
C31 C30 C37 C36 -173.73(19) . . . . ?
C29 C30 C37 C32 128.31(17) . . . . ?
C40 C30 C37 C32 -105.03(18) . . . . ?
C31 C30 C37 C32 5.94(18) . . . . ?
C29 C30 C40 F6 -171.99(18) . . . . ?
C37 C30 C40 F6 58.4(2) . . . . ?
C31 C30 C40 F6 -50.1(2) . . . . ?
C29 C30 C40 F5 69.2(2) . . . . ?
C37 C30 C40 F5 -60.4(2) . . . . ?
C31 C30 C40 F5 -168.85(16) . . . . ?
C29 C30 C40 F7 -52.5(2) . . . . ?
C37 C30 C40 F7 177.94(17) . . . . ?
C31 C30 C40 F7 69.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.920
_diffrn_reflns_theta_full        65.98
_diffrn_measured_fraction_theta_full 0.920
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.054
