# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Raymond Ziessel'
_publ_contact_author_email       ZIESSEL@CHIMIE.U-STRASBG.FR

_publ_section_title              
;
Terpyridine-Functionalised Imidazolium Ionic Liquids
;
loop_
_publ_author_name
'Raymond Ziessel'
'Franck Camerel'
'Jean-Hubert Olivier'
'Pascal Retailleau'
'Joseph Selb'

# Attachment 'tosupersede_ccdc_694700.cif'

data_jho385
_database_code_depnum_ccdc_archive 'CCDC 694700'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H24 N5, F6 P'
_chemical_formula_sum            'C23 H24 F6 N5 P'
_chemical_formula_weight         515.44

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.441(2)
_cell_length_b                   9.001(2)
_cell_length_c                   29.937(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.36(2)
_cell_angle_gamma                90.00
_cell_volume                     2441.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3180
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      22.46

_exptl_crystal_description       'large parallelepiped'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1.16
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
Single large crystals of [C4terpim]PF6 suitable for X-ray diffraction
were isolated by slow diffusion of methanol into a concentrated
dichloromethane solution. Crystals with different sizes were tested.
Choice for a crystal with a long dimension (parallel to b axis)
mainly maintained perpendicular to the incident radiation
during the data collection was held in order to maximize diffraction
resolution limits. Nevertheless no diffraction could be detectable
beyond 22.6\% (likely related to high dynamic molecular disorder
inside the crystal at room temperature).
Crystal size, even with collimator size adjustment,
is not really a problem for organic compound structure,
see Gorbitz, Acta Cryst. B55 (1999) 1090-98. Multi-scan absorption
correction appears to handle "the convoluted effects of a large crystal
and a non-uniform beam satisfactorily".
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11765
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         22.57
_reflns_number_total             3185
_reflns_number_gt                2282
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'DENZO (Otwinowski & Minor, 1997) COLLECT (Nonius B.V., 1999)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections except two reflections.
The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
Disorder of the butyl chain was solved by refining the two central carbons
over two positions with site occupation factors equal to 0.65 and 0.35
respectively. Idem for the four F atoms in the square plane of PF6 solvent
molecule with site occupation factors freely refined. Restraints on bond
lengths and ADP were applied to the PF6.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+1.3341P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3183
_refine_ls_number_parameters     372
_refine_ls_number_restraints     305
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1597
_refine_ls_wR_factor_gt          0.1405
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.090
_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
P1 P 0.39406(11) -0.44310(10) 0.80325(3) 0.0703(4) Uani 1 1 d DU . .
F1A F 0.3620(7) -0.3780(11) 0.75299(17) 0.117(5) Uani 0.257(9) 1 d PDU A 1
F2A F 0.2417(7) -0.5236(12) 0.7888(2) 0.140(6) Uani 0.257(9) 1 d PDU A 1
F3A F 0.4297(9) -0.5155(14) 0.8525(2) 0.137(5) Uani 0.257(9) 1 d PDU A 1
F4A F 0.5513(7) -0.3758(16) 0.8148(3) 0.148(5) Uani 0.257(9) 1 d PDU A 1
F1B F 0.2567(4) -0.4379(5) 0.75991(12) 0.133(2) Uani 0.743(9) 1 d PDU A 2
F2B F 0.3138(5) -0.5563(5) 0.82731(15) 0.135(2) Uani 0.743(9) 1 d PDU A 2
F3B F 0.5285(5) -0.4403(6) 0.84740(13) 0.157(3) Uani 0.743(9) 1 d PDU A 2
F4B F 0.4724(4) -0.3279(4) 0.77881(15) 0.118(2) Uani 0.743(9) 1 d PDU A 2
F5 F 0.4620(3) -0.5764(3) 0.78283(11) 0.1352(11) Uani 1 1 d DU A .
F6 F 0.3232(3) -0.3091(3) 0.82263(9) 0.1235(10) Uani 1 1 d DU A .
N1 N -0.0712(3) -0.0854(4) 0.85626(11) 0.0797(10) Uani 1 1 d . . .
N2 N 0.2463(3) 0.0943(3) 0.93107(9) 0.0618(8) Uani 1 1 d . . .
N3 N 0.6163(4) 0.2133(4) 0.97968(12) 0.0930(11) Uani 1 1 d . . .
N4 N 0.2679(3) 0.0542(3) 0.76505(9) 0.0586(8) Uani 1 1 d . . .
N5 N 0.1062(4) -0.0372(4) 0.70593(10) 0.0721(9) Uani 1 1 d . C .
C1 C 0.0122(4) -0.0198(4) 0.89425(12) 0.0601(9) Uani 1 1 d . . .
C2 C -0.1786(5) -0.0378(5) 0.93166(15) 0.0922(14) Uani 1 1 d . . .
H2 H -0.2146 -0.0206 0.9571 0.111 Uiso 1 1 calc R . .
C3 C -0.2644(5) -0.1059(5) 0.89307(16) 0.0862(12) Uani 1 1 d . . .
H3 H -0.3595 -0.1373 0.8916 0.103 Uiso 1 1 calc R . .
C4 C -0.2069(5) -0.1271(5) 0.85625(15) 0.0912(13) Uani 1 1 d . . .
H4 H -0.2660 -0.1731 0.8297 0.109 Uiso 1 1 calc R . .
C5 C -0.0379(4) 0.0056(5) 0.93294(13) 0.0817(12) Uani 1 1 d . . .
H5 H 0.0227 0.0512 0.9593 0.098 Uiso 1 1 calc R . .
C6 C 0.1604(4) 0.0318(4) 0.89259(11) 0.0562(9) Uani 1 1 d . . .
C7 C 0.2030(4) 0.0173(4) 0.85194(11) 0.0579(9) Uani 1 1 d . . .
H7 H 0.1411 -0.0287 0.8259 0.069 Uiso 1 1 calc R . .
C8 C 0.3382(4) 0.0721(4) 0.85082(11) 0.0577(9) Uani 1 1 d . . .
C9 C 0.4286(4) 0.1352(4) 0.89076(11) 0.0634(10) Uani 1 1 d . . .
H9 H 0.5210 0.1720 0.8912 0.076 Uiso 1 1 calc R . .
C10 C 0.3792(4) 0.1430(4) 0.93044(11) 0.0596(9) Uani 1 1 d . . .
C11 C 0.4725(5) 0.2103(4) 0.97415(12) 0.0708(10) Uani 1 1 d . . .
C12 C 0.4110(5) 0.2669(6) 1.00715(15) 0.1043(16) Uani 1 1 d . . .
H12 H 0.3093 0.2644 1.0023 0.125 Uiso 1 1 calc R . .
C13 C 0.7016(6) 0.2718(6) 1.01958(18) 0.1134(17) Uani 1 1 d . . .
H13 H 0.8032 0.2735 1.0240 0.136 Uiso 1 1 calc R . .
C14 C 0.6489(7) 0.3285(7) 1.05392(16) 0.1185(19) Uani 1 1 d . . .
H14 H 0.7125 0.3670 1.0810 0.142 Uiso 1 1 calc R . .
C15 C 0.5016(7) 0.3273(7) 1.04740(16) 0.127(2) Uani 1 1 d . . .
H15 H 0.4615 0.3668 1.0699 0.152 Uiso 1 1 calc R . .
C16 C 0.3914(4) 0.0641(5) 0.80748(11) 0.0704(10) Uani 1 1 d . . .
H16A H 0.4495 0.1518 0.8059 0.084 Uiso 1 1 calc R . .
H16B H 0.4546 -0.0221 0.8095 0.084 Uiso 1 1 calc R . .
C17 C 0.1704(4) 0.1641(4) 0.74639(13) 0.0712(11) Uani 1 1 d . . .
H17 H 0.1731 0.2611 0.7573 0.085 Uiso 1 1 calc R . .
C18 C 0.0708(5) 0.1080(5) 0.70984(14) 0.0776(11) Uani 1 1 d . . .
H18 H -0.0089 0.1586 0.6904 0.093 Uiso 1 1 calc R . .
C19 C 0.2267(5) -0.0661(4) 0.73972(13) 0.0705(10) Uani 1 1 d . . .
H19 H 0.2750 -0.1572 0.7449 0.085 Uiso 1 1 calc R . .
C20 C 0.0290(5) -0.1426(5) 0.66958(13) 0.1046(15) Uani 1 1 d DU . .
H20A H -0.0667 -0.1651 0.6739 0.125 Uiso 0.65 1 calc PR B 1
H20B H 0.0850 -0.2344 0.6734 0.125 Uiso 0.65 1 calc PR B 1
H20C H -0.0714 -0.1096 0.6553 0.125 Uiso 0.35 1 calc PR B 2
H20D H 0.0257 -0.2403 0.6829 0.125 Uiso 0.35 1 calc PR B 2
C21A C 0.0069(7) -0.0869(9) 0.62070(18) 0.102(2) Uani 0.65 1 d PDU C 1
H21A H -0.0603 -0.1519 0.5988 0.122 Uiso 0.65 1 calc PR C 1
H21B H -0.0354 0.0121 0.6175 0.122 Uiso 0.65 1 calc PR C 1
C22A C 0.1541(8) -0.0838(12) 0.6106(2) 0.130(3) Uani 0.65 1 d PDU C 1
H22A H 0.1958 -0.1830 0.6132 0.155 Uiso 0.65 1 calc PR C 1
H22B H 0.2219 -0.0199 0.6327 0.155 Uiso 0.65 1 calc PR C 1
C21B C 0.1148(15) -0.1482(14) 0.6336(4) 0.122(4) Uani 0.35 1 d PDU C 2
H21C H 0.2199 -0.1542 0.6489 0.146 Uiso 0.35 1 calc PR C 2
H21D H 0.0862 -0.2351 0.6139 0.146 Uiso 0.35 1 calc PR C 2
C22B C 0.081(2) -0.0096(14) 0.6047(4) 0.142(4) Uani 0.35 1 d PDU C 2
H22C H -0.0245 0.0090 0.5959 0.170 Uiso 0.35 1 calc PR C 2
H22D H 0.1303 0.0745 0.6228 0.170 Uiso 0.35 1 calc PR C 2
C23 C 0.1317(9) -0.0258(9) 0.56193(18) 0.204(3) Uani 1 1 d DU . .
H23A H 0.2242 -0.0261 0.5545 0.307 Uiso 0.65 1 calc PR C 1
H23B H 0.0940 0.0738 0.5599 0.307 Uiso 0.65 1 calc PR C 1
H23C H 0.0624 -0.0880 0.5403 0.307 Uiso 0.65 1 calc PR C 1
H23D H 0.1122 0.0646 0.5442 0.307 Uiso 0.35 1 calc PR C 2
H23E H 0.0796 -0.1063 0.5434 0.307 Uiso 0.35 1 calc PR C 2
H23F H 0.2357 -0.0459 0.5707 0.307 Uiso 0.35 1 calc PR C 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0797(8) 0.0593(6) 0.0760(7) -0.0045(5) 0.0288(6) -0.0005(5)
F1A 0.141(12) 0.143(10) 0.075(4) 0.010(5) 0.041(6) 0.043(9)
F2A 0.088(5) 0.133(11) 0.201(15) -0.042(10) 0.045(8) -0.035(7)
F3A 0.206(16) 0.107(10) 0.098(5) 0.029(6) 0.039(7) 0.012(9)
F4A 0.094(5) 0.159(11) 0.175(13) 0.001(10) 0.010(7) -0.051(6)
F1B 0.109(3) 0.158(5) 0.106(3) -0.011(3) -0.011(3) -0.007(3)
F2B 0.168(6) 0.094(3) 0.176(6) 0.036(4) 0.103(5) -0.002(3)
F3B 0.133(4) 0.185(6) 0.118(3) 0.003(3) -0.022(3) 0.010(3)
F4B 0.123(4) 0.089(2) 0.169(5) 0.021(3) 0.087(4) -0.004(2)
F5 0.164(3) 0.0840(16) 0.191(3) -0.0170(17) 0.105(2) 0.0226(16)
F6 0.185(3) 0.0825(16) 0.127(2) -0.0124(14) 0.082(2) 0.0237(17)
N1 0.069(2) 0.100(2) 0.077(2) -0.0211(19) 0.0319(18) -0.0177(19)
N2 0.071(2) 0.0645(18) 0.0546(17) -0.0010(14) 0.0251(15) -0.0044(16)
N3 0.075(2) 0.123(3) 0.075(2) -0.013(2) 0.012(2) -0.003(2)
N4 0.0653(19) 0.0657(19) 0.0519(17) 0.0008(15) 0.0281(15) -0.0007(16)
N5 0.086(2) 0.073(2) 0.0608(19) -0.0022(16) 0.0270(19) -0.0150(18)
C1 0.066(2) 0.061(2) 0.056(2) -0.0006(17) 0.0223(19) 0.0011(18)
C2 0.080(3) 0.129(4) 0.082(3) -0.007(3) 0.046(3) -0.006(3)
C3 0.071(3) 0.103(3) 0.095(3) -0.002(3) 0.039(3) -0.007(2)
C4 0.071(3) 0.116(4) 0.090(3) -0.028(3) 0.029(2) -0.019(3)
C5 0.081(3) 0.111(3) 0.062(2) -0.014(2) 0.034(2) -0.016(2)
C6 0.063(2) 0.056(2) 0.056(2) 0.0036(16) 0.0261(18) 0.0007(17)
C7 0.066(2) 0.060(2) 0.0507(19) -0.0008(16) 0.0202(17) -0.0025(18)
C8 0.063(2) 0.064(2) 0.0499(19) 0.0038(16) 0.0224(17) 0.0027(18)
C9 0.061(2) 0.070(2) 0.062(2) 0.0053(18) 0.0212(19) -0.0037(19)
C10 0.067(2) 0.062(2) 0.053(2) 0.0017(16) 0.0222(18) -0.0004(19)
C11 0.078(3) 0.077(2) 0.058(2) 0.0007(19) 0.021(2) -0.012(2)
C12 0.104(4) 0.141(4) 0.079(3) -0.036(3) 0.043(3) -0.048(3)
C13 0.086(3) 0.155(5) 0.086(3) -0.013(3) 0.003(3) -0.023(3)
C14 0.131(5) 0.153(5) 0.066(3) -0.021(3) 0.018(3) -0.053(4)
C15 0.137(5) 0.175(5) 0.080(3) -0.049(3) 0.052(3) -0.069(4)
C16 0.064(2) 0.095(3) 0.057(2) -0.0002(19) 0.0252(19) -0.001(2)
C17 0.088(3) 0.064(2) 0.066(2) -0.002(2) 0.029(2) 0.008(2)
C18 0.083(3) 0.084(3) 0.066(3) 0.009(2) 0.023(2) 0.011(2)
C19 0.092(3) 0.062(2) 0.063(2) 0.002(2) 0.031(2) 0.004(2)
C20 0.126(4) 0.104(3) 0.083(3) -0.020(2) 0.029(3) -0.048(3)
C21A 0.101(5) 0.113(5) 0.082(4) -0.016(4) 0.010(4) -0.026(4)
C22A 0.135(6) 0.177(8) 0.091(4) -0.057(5) 0.055(4) -0.034(6)
C21B 0.148(9) 0.130(8) 0.092(7) -0.047(5) 0.041(6) -0.050(8)
C22B 0.180(10) 0.158(10) 0.104(7) -0.019(6) 0.068(7) -0.057(8)
C23 0.272(8) 0.254(8) 0.110(4) -0.034(5) 0.091(5) -0.065(7)

_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
P1 F4A 1.550(4) . ?
P1 F3B 1.554(3) . ?
P1 F1B 1.555(3) . ?
P1 F2A 1.559(4) . ?
P1 F3A 1.559(4) . ?
P1 F2B 1.562(3) . ?
P1 F1A 1.563(4) . ?
P1 F5 1.564(2) . ?
P1 F6 1.568(2) . ?
P1 F4B 1.569(3) . ?
N1 C1 1.326(4) . ?
N1 C4 1.335(5) . ?
N2 C6 1.332(4) . ?
N2 C10 1.334(4) . ?
N3 C11 1.320(5) . ?
N3 C13 1.346(5) . ?
N4 C19 1.316(4) . ?
N4 C17 1.360(4) . ?
N4 C16 1.465(4) . ?
N5 C19 1.318(5) . ?
N5 C18 1.362(5) . ?
N5 C20 1.473(5) . ?
C1 C5 1.388(5) . ?
C1 C6 1.488(5) . ?
C2 C3 1.357(5) . ?
C2 C5 1.375(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(5) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.391(4) . ?
C7 C8 1.378(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(5) . ?
C8 C16 1.520(4) . ?
C9 C10 1.395(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.485(5) . ?
C11 C12 1.377(5) . ?
C12 C15 1.378(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.349(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.325(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21A 1.505(4) . ?
C20 C21B 1.521(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C20 H20D 0.9700 . ?
C21A C22A 1.504(5) . ?
C21A H21A 0.9700 . ?
C21A H21B 0.9700 . ?
C22A C23 1.505(5) . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
C21B C22B 1.500(5) . ?
C21B H21C 0.9700 . ?
C21B H21D 0.9700 . ?
C22B C23 1.494(5) . ?
C22B H22C 0.9700 . ?
C22B H22D 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 H23D 0.9600 . ?
C23 H23E 0.9600 . ?
C23 H23F 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
F4A P1 F3B 45.73(15) . . ?
F4A P1 F1B 134.1(2) . . ?
F3B P1 F1B 177.0(3) . . ?
F4A P1 F2A 174.0(8) . . ?
F3B P1 F2A 135.5(2) . . ?
F1B P1 F2A 45.18(15) . . ?
F4A P1 F3A 90.8(2) . . ?
F3B P1 F3A 45.23(15) . . ?
F1B P1 F3A 135.1(2) . . ?
F2A P1 F3A 90.3(2) . . ?
F4A P1 F2B 135.3(2) . . ?
F3B P1 F2B 90.27(19) . . ?
F1B P1 F2B 90.31(18) . . ?
F2A P1 F2B 45.19(15) . . ?
F3A P1 F2B 45.14(15) . . ?
F4A P1 F1A 89.0(2) . . ?
F3B P1 F1A 134.7(2) . . ?
F1B P1 F1A 45.22(15) . . ?
F2A P1 F1A 89.6(2) . . ?
F3A P1 F1A 176.9(7) . . ?
F2B P1 F1A 134.5(2) . . ?
F4A P1 F5 85.1(6) . . ?
F3B P1 F5 91.0(3) . . ?
F1B P1 F5 92.0(2) . . ?
F2A P1 F5 89.0(5) . . ?
F3A P1 F5 92.6(6) . . ?
F2B P1 F5 89.2(2) . . ?
F1A P1 F5 84.3(4) . . ?
F4A P1 F6 95.7(7) . . ?
F3B P1 F6 90.3(2) . . ?
F1B P1 F6 86.7(2) . . ?
F2A P1 F6 90.2(5) . . ?
F3A P1 F6 88.5(6) . . ?
F2B P1 F6 91.0(2) . . ?
F1A P1 F6 94.6(4) . . ?
F5 P1 F6 178.69(19) . . ?
F4A P1 F4B 45.40(15) . . ?
F3B P1 F4B 90.4(2) . . ?
F1B P1 F4B 89.02(19) . . ?
F2A P1 F4B 134.2(2) . . ?
F3A P1 F4B 135.4(2) . . ?
F2B P1 F4B 179.1(2) . . ?
F5 P1 F4B 91.46(19) . . ?
F6 P1 F4B 88.33(19) . . ?
C1 N1 C4 117.6(3) . . ?
C6 N2 C10 118.2(3) . . ?
C11 N3 C13 117.2(4) . . ?
C19 N4 C17 107.8(3) . . ?
C19 N4 C16 125.7(3) . . ?
C17 N4 C16 126.4(3) . . ?
C19 N5 C18 107.7(3) . . ?
C19 N5 C20 125.5(4) . . ?
C18 N5 C20 126.8(4) . . ?
N1 C1 C5 122.0(3) . . ?
N1 C1 C6 116.6(3) . . ?
C5 C1 C6 121.4(3) . . ?
C3 C2 C5 119.5(4) . . ?
C3 C2 H2 120.2 . . ?
C5 C2 H2 120.2 . . ?
C2 C3 C4 118.0(4) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
N1 C4 C3 123.9(4) . . ?
N1 C4 H4 118.0 . . ?
C3 C4 H4 118.0 . . ?
C2 C5 C1 118.9(4) . . ?
C2 C5 H5 120.5 . . ?
C1 C5 H5 120.5 . . ?
N2 C6 C7 122.7(3) . . ?
N2 C6 C1 116.9(3) . . ?
C7 C6 C1 120.4(3) . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 118.5(3) . . ?
C7 C8 C16 122.4(3) . . ?
C9 C8 C16 119.1(3) . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
N2 C10 C9 122.5(3) . . ?
N2 C10 C11 116.6(3) . . ?
C9 C10 C11 120.9(3) . . ?
N3 C11 C12 121.9(4) . . ?
N3 C11 C10 116.9(3) . . ?
C12 C11 C10 121.2(4) . . ?
C11 C12 C15 119.4(5) . . ?
C11 C12 H12 120.3 . . ?
C15 C12 H12 120.3 . . ?
N3 C13 C14 124.2(5) . . ?
N3 C13 H13 117.9 . . ?
C14 C13 H13 117.9 . . ?
C15 C14 C13 118.0(5) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C12 119.4(5) . . ?
C14 C15 H15 120.3 . . ?
C12 C15 H15 120.3 . . ?
N4 C16 C8 111.7(3) . . ?
N4 C16 H16A 109.3 . . ?
C8 C16 H16A 109.3 . . ?
N4 C16 H16B 109.3 . . ?
C8 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 N4 107.6(3) . . ?
C18 C17 H17 126.2 . . ?
N4 C17 H17 126.2 . . ?
C17 C18 N5 107.6(4) . . ?
C17 C18 H18 126.2 . . ?
N5 C18 H18 126.2 . . ?
N4 C19 N5 109.3(3) . . ?
N4 C19 H19 125.3 . . ?
N5 C19 H19 125.3 . . ?
N5 C20 C21A 114.1(4) . . ?
N5 C20 C21B 107.1(7) . . ?
N5 C20 H20A 108.7 . . ?
C21A C20 H20A 108.7 . . ?
C21B C20 H20A 142.3 . . ?
N5 C20 H20B 108.7 . . ?
C21A C20 H20B 108.7 . . ?
C21B C20 H20B 71.0 . . ?
H20A C20 H20B 107.6 . . ?
N5 C20 H20C 110.3 . . ?
C21A C20 H20C 67.6 . . ?
C21B C20 H20C 110.3 . . ?
H20B C20 H20C 138.2 . . ?
N5 C20 H20D 110.3 . . ?
C21A C20 H20D 133.7 . . ?
C21B C20 H20D 110.3 . . ?
H20A C20 H20D 67.4 . . ?
H20C C20 H20D 108.6 . . ?
C22A C21A C20 108.6(4) . . ?
C22A C21A H21A 110.0 . . ?
C20 C21A H21A 110.0 . . ?
C22A C21A H21B 110.0 . . ?
C20 C21A H21B 110.0 . . ?
H21A C21A H21B 108.3 . . ?
C21A C22A C23 108.4(5) . . ?
C21A C22A H22A 110.0 . . ?
C23 C22A H22A 110.0 . . ?
C21A C22A H22B 110.0 . . ?
C23 C22A H22B 110.0 . . ?
H22A C22A H22B 108.4 . . ?
C22B C21B C20 108.1(6) . . ?
C22B C21B H21C 110.1 . . ?
C20 C21B H21C 110.1 . . ?
C22B C21B H21D 110.1 . . ?
C20 C21B H21D 110.1 . . ?
H21C C21B H21D 108.4 . . ?
C23 C22B C21B 110.2(6) . . ?
C23 C22B H22C 109.6 . . ?
C21B C22B H22C 109.6 . . ?
C23 C22B H22D 109.6 . . ?
C21B C22B H22D 109.6 . . ?
H22C C22B H22D 108.1 . . ?
C22B C23 H23A 136.9 . . ?
C22A C23 H23A 109.5 . . ?
C22B C23 H23B 76.1 . . ?
C22A C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22B C23 H23C 108.2 . . ?
C22A C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22B C23 H23D 109.5 . . ?
C22A C23 H23D 141.4 . . ?
H23A C23 H23D 85.4 . . ?
H23C C23 H23D 97.7 . . ?
C22B C23 H23E 109.5 . . ?
C22A C23 H23E 102.0 . . ?
H23A C23 H23E 102.4 . . ?
H23B C23 H23E 123.3 . . ?
H23D C23 H23E 109.5 . . ?
C22B C23 H23F 109.5 . . ?
C22A C23 H23F 79.3 . . ?
H23B C23 H23F 121.7 . . ?
H23C C23 H23F 121.6 . . ?
H23D C23 H23F 109.5 . . ?
H23E C23 H23F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C5 0.0(6) . . . . ?
C4 N1 C1 C6 -177.3(4) . . . . ?
C5 C2 C3 C4 -0.8(7) . . . . ?
C1 N1 C4 C3 0.0(7) . . . . ?
C2 C3 C4 N1 0.4(8) . . . . ?
C3 C2 C5 C1 0.8(7) . . . . ?
N1 C1 C5 C2 -0.4(6) . . . . ?
C6 C1 C5 C2 176.7(4) . . . . ?
C10 N2 C6 C7 -0.9(5) . . . . ?
C10 N2 C6 C1 -179.4(3) . . . . ?
N1 C1 C6 N2 -178.3(3) . . . . ?
C5 C1 C6 N2 4.4(5) . . . . ?
N1 C1 C6 C7 3.2(5) . . . . ?
C5 C1 C6 C7 -174.1(3) . . . . ?
N2 C6 C7 C8 -1.3(5) . . . . ?
C1 C6 C7 C8 177.1(3) . . . . ?
C6 C7 C8 C9 2.1(5) . . . . ?
C6 C7 C8 C16 -178.5(3) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
C16 C8 C9 C10 179.7(3) . . . . ?
C6 N2 C10 C9 2.2(5) . . . . ?
C6 N2 C10 C11 -179.3(3) . . . . ?
C8 C9 C10 N2 -1.4(5) . . . . ?
C8 C9 C10 C11 -179.8(3) . . . . ?
C13 N3 C11 C12 1.3(7) . . . . ?
C13 N3 C11 C10 -178.9(4) . . . . ?
N2 C10 C11 N3 158.1(3) . . . . ?
C9 C10 C11 N3 -23.3(5) . . . . ?
N2 C10 C11 C12 -22.0(6) . . . . ?
C9 C10 C11 C12 156.5(4) . . . . ?
N3 C11 C12 C15 -0.7(7) . . . . ?
C10 C11 C12 C15 179.5(4) . . . . ?
C11 N3 C13 C14 -0.7(8) . . . . ?
N3 C13 C14 C15 -0.6(9) . . . . ?
C13 C14 C15 C12 1.2(9) . . . . ?
C11 C12 C15 C14 -0.6(9) . . . . ?
C19 N4 C16 C8 -105.4(4) . . . . ?
C17 N4 C16 C8 70.3(4) . . . . ?
C7 C8 C16 N4 24.4(5) . . . . ?
C9 C8 C16 N4 -156.2(3) . . . . ?
C19 N4 C17 C18 0.1(4) . . . . ?
C16 N4 C17 C18 -176.2(3) . . . . ?
N4 C17 C18 N5 0.2(4) . . . . ?
C19 N5 C18 C17 -0.5(4) . . . . ?
C20 N5 C18 C17 -178.1(3) . . . . ?
C17 N4 C19 N5 -0.5(4) . . . . ?
C16 N4 C19 N5 175.9(3) . . . . ?
C18 N5 C19 N4 0.6(4) . . . . ?
C20 N5 C19 N4 178.2(3) . . . . ?
C19 N5 C20 C21A -125.2(5) . . . . ?
C18 N5 C20 C21A 52.0(6) . . . . ?
C19 N5 C20 C21B -78.9(6) . . . . ?
C18 N5 C20 C21B 98.2(6) . . . . ?
N5 C20 C21A C22A 70.6(8) . . . . ?
C21B C20 C21A C22A -19.2(9) . . . . ?
C20 C21A C22A C23 -179.1(6) . . . . ?
N5 C20 C21B C22B -75.9(13) . . . . ?
C21A C20 C21B C22B 31.3(10) . . . . ?
C20 C21B C22B C23 -166.1(12) . . . . ?
C21B C22B C23 C22A -22.0(9) . . . . ?
C21A C22A C23 C22B 36.5(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        22.57
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.035