# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_smjl211

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"Hexamethylenetetramine 5,10,15,20-tetra(perfluoro-4'-iodophenyl)porphyrin"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H10 F16 I4 N4, C6 H12 N4'
_chemical_formula_sum            'C50 H22 F16 I4 N8'
_chemical_formula_weight         1546.36

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'
I I -0.4742 1.8119 '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 2/c'
_symmetry_space_group_name_Hall  '-P 2yc'

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

_cell_length_a                   27.319(3)
_cell_length_b                   8.7331(7)
_cell_length_c                   55.699(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.685(9)
_cell_angle_gamma                90.00
_cell_volume                     13223(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    62
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      17.22

_exptl_crystal_description       plate-like
_exptl_crystal_colour            blue-violet
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5872
_exptl_absorpt_coefficient_mu    1.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5455
_exptl_absorpt_correction_T_max  0.8033
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_method       CCD
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            148609
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -78
_diffrn_reflns_limit_l_max       78
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         30.00
_reflns_number_total             38466
_reflns_number_gt                20516
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius BV, 1997-2000)'
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0002P)²+0.0000P] 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       0.00026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         38466
_refine_ls_number_parameters     1406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.386322(14) 0.85490(6) 0.130239(9) 0.04243(14) Uani 1 1 d . . .
I2 I 0.19748(2) -0.14986(7) 0.215492(9) 0.06878(19) Uani 1 1 d . . .
I3 I 0.34862(2) 0.94264(10) 0.064809(10) 0.0941(3) Uani 1 1 d . . .
I4 I 0.093992(18) 0.89881(8) 0.094192(13) 0.0796(2) Uani 1 1 d . . .
N1 N 0.70118(18) 0.9195(6) 0.13833(9) 0.0314(13) Uani 1 1 d . . .
H1 H 0.7167 0.9466 0.1263 0.038 Uiso 1 1 calc R . .
N2 N 0.80460(17) 0.9493(6) 0.13133(9) 0.0286(12) Uani 1 1 d . . .
N3 N 0.77976(17) 0.9741(6) 0.07950(9) 0.0284(13) Uani 1 1 d . . .
H3 H 0.7637 0.9706 0.0920 0.034 Uiso 1 1 calc R . .
N4 N 0.67574(16) 0.9573(6) 0.08703(9) 0.0281(12) Uani 1 1 d . . .
C1 C 0.6173(2) 0.9115(7) 0.11738(12) 0.0325(16) Uani 1 1 d . . .
C2 C 0.6517(2) 0.8911(7) 0.13808(11) 0.0310(16) Uani 1 1 d . . .
C3 C 0.6412(2) 0.8450(8) 0.16170(12) 0.0411(18) Uani 1 1 d . . .
H3A H 0.6105 0.8186 0.1664 0.049 Uiso 1 1 calc R . .
C4 C 0.6828(2) 0.8473(8) 0.17536(12) 0.0355(17) Uani 1 1 d . . .
H4 H 0.6870 0.8210 0.1916 0.043 Uiso 1 1 calc R . .
C5 C 0.7205(2) 0.8960(7) 0.16154(11) 0.0309(16) Uani 1 1 d . . .
C6 C 0.7700(2) 0.9110(7) 0.16970(11) 0.0270(15) Uani 1 1 d . . .
C7 C 0.8080(2) 0.9342(7) 0.15614(11) 0.0297(15) Uani 1 1 d . . .
C8 C 0.8597(2) 0.9325(8) 0.16499(13) 0.0429(18) Uani 1 1 d . . .
H8 H 0.8728 0.9282 0.1810 0.052 Uiso 1 1 calc R . .
C9 C 0.8856(2) 0.9384(8) 0.14507(12) 0.0396(18) Uani 1 1 d . . .
H9 H 0.9197 0.9361 0.1453 0.048 Uiso 1 1 calc R . .
C10 C 0.8514(2) 0.9485(7) 0.12392(11) 0.0299(15) Uani 1 1 d . . .
C11 C 0.8635(2) 0.9559(8) 0.10051(12) 0.0351(17) Uani 1 1 d . . .
C12 C 0.8281(2) 0.9682(7) 0.07927(12) 0.0324(16) Uani 1 1 d . . .
C13 C 0.8404(3) 0.9738(8) 0.05536(12) 0.0413(18) Uani 1 1 d . . .
H13 H 0.8719 0.9708 0.0504 0.050 Uiso 1 1 calc R . .
C14 C 0.7974(2) 0.9845(8) 0.04091(12) 0.0378(18) Uani 1 1 d . . .
H14 H 0.7935 0.9893 0.0241 0.045 Uiso 1 1 calc R . .
C15 C 0.7605(2) 0.9866(7) 0.05642(11) 0.0263(15) Uani 1 1 d . . .
C16 C 0.7115(2) 0.9940(8) 0.04880(11) 0.0326(16) Uani 1 1 d . . .
C17 C 0.6719(2) 0.9858(7) 0.06317(11) 0.0310(16) Uani 1 1 d . . .
C18 C 0.6212(2) 1.0005(8) 0.05463(12) 0.0413(18) Uani 1 1 d . . .
H18 H 0.6088 1.0219 0.0388 0.050 Uiso 1 1 calc R . .
C19 C 0.5946(2) 0.9780(8) 0.07337(12) 0.0385(18) Uani 1 1 d . . .
H19 H 0.5605 0.9819 0.0731 0.046 Uiso 1 1 calc R . .
C20 C 0.6294(2) 0.9466(7) 0.09399(11) 0.0295(15) Uani 1 1 d . . .
C21 C 0.5630(2) 0.8957(7) 0.12123(12) 0.0293(16) Uani 1 1 d . . .
C22 C 0.5395(2) 0.9767(8) 0.13750(11) 0.0306(16) Uani 1 1 d . . .
C23 C 0.4934(2) 0.9655(8) 0.14049(12) 0.0344(17) Uani 1 1 d . . .
C24 C 0.4627(2) 0.8679(9) 0.12585(13) 0.0388(18) Uani 1 1 d . . .
C25 C 0.4845(2) 0.7820(8) 0.10954(12) 0.0341(17) Uani 1 1 d . . .
C26 C 0.5319(2) 0.7933(8) 0.10737(12) 0.0370(17) Uani 1 1 d . . .
C27 C 0.2184(2) -0.1047(8) 0.30423(12) 0.0317(16) Uani 1 1 d . . .
C28 C 0.2155(3) -0.2423(10) 0.29321(13) 0.048(2) Uani 1 1 d . . .
C29 C 0.2078(3) -0.2532(9) 0.26830(14) 0.048(2) Uani 1 1 d . . .
C30 C 0.2024(2) -0.1339(10) 0.25327(12) 0.0430(18) Uani 1 1 d . . .
C31 C 0.2046(3) 0.0070(10) 0.26449(15) 0.054(2) Uani 1 1 d . . .
C32 C 0.2119(3) 0.0186(9) 0.28940(14) 0.0445(19) Uani 1 1 d . . .
C33 C 0.9169(2) 0.9429(9) 0.09695(11) 0.0354(17) Uani 1 1 d . . .
C34 C 0.9408(3) 0.8042(9) 0.09679(15) 0.051(2) Uani 1 1 d . . .
C35 C 0.9884(3) 0.7893(10) 0.09520(15) 0.056(2) Uani 1 1 d . . .
C36 C 0.0170(2) 0.9169(11) 0.09379(14) 0.055(2) Uani 1 1 d . . .
C37 C 0.9950(3) 1.0558(11) 0.09377(15) 0.057(2) Uani 1 1 d . . .
C38 C 0.9463(3) 1.0674(9) 0.09443(14) 0.051(2) Uani 1 1 d . . .
C39 C 0.6979(2) 1.0098(9) 0.02177(11) 0.0355(17) Uani 1 1 d . . .
C40 C 0.6955(3) 0.8856(11) 0.00732(14) 0.054(2) Uani 1 1 d . . .
C41 C 0.6843(3) 0.8963(11) -0.01708(17) 0.071(3) Uani 1 1 d . . .
C42 C 0.3259(3) 0.9676(12) 0.02798(13) 0.058(2) Uani 1 1 d . . .
C43 C 0.6762(3) 1.1621(11) -0.01295(16) 0.069(3) Uani 1 1 d . . .
C44 C 0.6872(3) 1.1488(10) 0.01131(13) 0.051(2) Uani 1 1 d . . .
F1 F 0.56704(12) 1.0800(5) 0.15142(7) 0.0445(10) Uani 1 1 d . . .
F2 F 0.47398(13) 1.0515(5) 0.15750(7) 0.0524(11) Uani 1 1 d . . .
F3 F 0.45701(13) 0.6856(5) 0.09498(8) 0.0563(12) Uani 1 1 d . . .
F4 F 0.55094(12) 0.7024(5) 0.09084(7) 0.0473(10) Uani 1 1 d . . .
F5 F 0.22098(19) -0.3733(5) 0.30585(8) 0.0755(14) Uani 1 1 d . . .
F6 F 0.2055(2) -0.3997(6) 0.25841(8) 0.0871(17) Uani 1 1 d . . .
F7 F 0.1978(2) 0.1363(6) 0.25124(8) 0.0874(16) Uani 1 1 d . . .
F8 F 0.21418(19) 0.1596(5) 0.29902(8) 0.0748(14) Uani 1 1 d . . .
F9 F 0.91398(16) 0.6771(5) 0.09882(12) 0.098(2) Uani 1 1 d . . .
F10 F 1.00853(17) 0.6514(6) 0.09603(14) 0.119(2) Uani 1 1 d . . .
F11 F 1.02090(16) 1.1841(6) 0.09193(13) 0.115(2) Uani 1 1 d . . .
F12 F 0.92579(16) 1.2073(6) 0.09416(12) 0.0952(19) Uani 1 1 d . . .
F13 F 0.7052(2) 0.7457(6) 0.01659(9) 0.0942(18) Uani 1 1 d . . .
F14 F 0.6826(3) 0.7701(8) -0.03108(10) 0.123(2) Uani 1 1 d . . .
F15 F 0.6651(3) 1.3017(7) -0.02247(10) 0.121(2) Uani 1 1 d . . .
F16 F 0.6854(2) 1.2754(6) 0.02486(9) 0.0941(18) Uani 1 1 d . . .
I5 I 0.610321(15) 0.37011(6) 0.115688(9) 0.04479(15) Uani 1 1 d . . .
I6 I 0.34659(2) 0.32218(11) 0.316552(10) 0.0999(3) Uani 1 1 d . . .
I7 I -0.096806(18) 0.38646(8) 0.153800(14) 0.0849(2) Uani 1 1 d . . .
I8 I 0.80103(2) 0.44108(8) 0.032327(9) 0.0735(2) Uani 1 1 d . . .
N9 N 0.32183(16) 0.3976(6) 0.16424(9) 0.0280(13) Uani 1 1 d . . .
H9A H 0.2959 0.4236 0.1551 0.034 Uiso 1 1 calc R . .
N10 N 0.21866(16) 0.4194(6) 0.17210(9) 0.0272(12) Uani 1 1 d . . .
N11 N 0.19467(17) 0.4492(6) 0.12046(9) 0.0301(13) Uani 1 1 d . . .
H11 H 0.2214 0.4477 0.1300 0.036 Uiso 1 1 calc R . .
N12 N 0.29766(16) 0.4359(6) 0.11323(9) 0.0295(13) Uani 1 1 d . . .
C51 C 0.3821(2) 0.3986(7) 0.13439(12) 0.0341(17) Uani 1 1 d . . .
C52 C 0.3682(2) 0.3746(7) 0.15771(11) 0.0316(15) Uani 1 1 d . . .
C53 C 0.4019(2) 0.3264(8) 0.17801(12) 0.0385(18) Uani 1 1 d . . .
H53 H 0.4350 0.3024 0.1779 0.046 Uiso 1 1 calc R . .
C54 C 0.3757(2) 0.3238(8) 0.19672(13) 0.045(2) Uani 1 1 d . . .
H54 H 0.3869 0.2973 0.2125 0.055 Uiso 1 1 calc R . .
C55 C 0.3259(2) 0.3706(8) 0.18786(11) 0.0314(15) Uani 1 1 d . . .
C56 C 0.2862(2) 0.3813(7) 0.20281(11) 0.0345(16) Uani 1 1 d . . .
C57 C 0.2381(2) 0.4021(7) 0.19541(11) 0.0275(15) Uani 1 1 d . . .
C58 C 0.2001(2) 0.3981(8) 0.21001(12) 0.0380(18) Uani 1 1 d . . .
H58 H 0.2033 0.3875 0.2267 0.046 Uiso 1 1 calc R . .
C59 C 0.1572(2) 0.4124(8) 0.19563(11) 0.0369(18) Uani 1 1 d . . .
H59 H 0.1256 0.4149 0.2006 0.044 Uiso 1 1 calc R . .
C60 C 0.1698(2) 0.4226(7) 0.17192(11) 0.0307(16) Uani 1 1 d . . .
C61 C 0.1351(2) 0.4311(7) 0.15086(12) 0.0311(16) Uani 1 1 d . . .
C62 C 0.1476(2) 0.4404(7) 0.12716(11) 0.0291(15) Uani 1 1 d . . .
C63 C 0.1119(2) 0.4408(8) 0.10659(12) 0.0426(18) Uani 1 1 d . . .
H63 H 0.0779 0.4327 0.1064 0.051 Uiso 1 1 calc R . .
C64 C 0.1395(2) 0.4561(8) 0.08671(12) 0.0436(19) Uani 1 1 d . . .
H64 H 0.1269 0.4620 0.0706 0.052 Uiso 1 1 calc R . .
C65 C 0.1911(2) 0.4609(8) 0.09575(11) 0.0335(17) Uani 1 1 d . . .
C66 C 0.2291(2) 0.4716(7) 0.08193(11) 0.0304(16) Uani 1 1 d . . .
C67 C 0.2787(2) 0.4664(7) 0.08996(11) 0.0316(16) Uani 1 1 d . . .
C68 C 0.3176(2) 0.4849(8) 0.07533(11) 0.0334(16) Uani 1 1 d . . .
H68 H 0.3144 0.5068 0.0589 0.040 Uiso 1 1 calc R . .
C69 C 0.3599(2) 0.4653(8) 0.08925(11) 0.0356(17) Uani 1 1 d . . .
H69 H 0.3913 0.4721 0.0843 0.043 Uiso 1 1 calc R . .
C70 C 0.3480(2) 0.4315(7) 0.11347(12) 0.0348(17) Uani 1 1 d . . .
C71 C 0.4365(2) 0.3889(8) 0.12996(12) 0.0329(17) Uani 1 1 d . . .
C72 C 0.4720(2) 0.4771(8) 0.14297(12) 0.0354(17) Uani 1 1 d . . .
C73 C 0.5187(2) 0.4713(8) 0.13919(12) 0.0347(17) Uani 1 1 d . . .
C74 C 0.5345(2) 0.3772(9) 0.12248(13) 0.0406(18) Uani 1 1 d . . .
C75 C 0.4999(2) 0.2887(8) 0.10901(12) 0.0350(17) Uani 1 1 d . . .
C76 C 0.4537(2) 0.2931(7) 0.11351(12) 0.0313(16) Uani 1 1 d . . .
C77 C 0.3004(2) 0.3647(9) 0.22943(12) 0.0348(16) Uani 1 1 d . . .
C78 C 0.3073(3) 0.4878(11) 0.24393(14) 0.058(2) Uani 1 1 d . . .
C79 C 0.3191(3) 0.4763(13) 0.26869(18) 0.077(3) Uani 1 1 d . . .
C80 C 0.3250(3) 0.3373(14) 0.28011(15) 0.069(3) Uani 1 1 d . . .
C81 C 0.3170(3) 0.2132(11) 0.26509(16) 0.062(2) Uani 1 1 d . . .
C82 C 0.3039(3) 0.2259(11) 0.24063(14) 0.055(2) Uani 1 1 d . . .
C83 C 0.0812(2) 0.4201(9) 0.15412(12) 0.0381(18) Uani 1 1 d . . .
C84 C 0.0518(3) 0.5493(10) 0.15465(14) 0.050(2) Uani 1 1 d . . .
C85 C 0.0033(3) 0.5394(10) 0.15503(16) 0.059(2) Uani 1 1 d . . .
C86 C -0.0198(3) 0.4047(11) 0.15536(14) 0.056(2) Uani 1 1 d . . .
C87 C 0.0083(3) 0.2724(10) 0.15514(16) 0.057(2) Uani 1 1 d . . .
C88 C 0.0574(2) 0.2854(9) 0.15467(14) 0.047(2) Uani 1 1 d . . .
C89 C 0.2172(2) 0.4959(9) 0.05555(11) 0.0304(16) Uani 1 1 d . . .
C90 C 0.2152(3) 0.6358(9) 0.04515(13) 0.0454(19) Uani 1 1 d . . .
C91 C 0.2070(3) 0.6538(10) 0.02065(14) 0.049(2) Uani 1 1 d . . .
C92 C 0.2031(3) 0.5332(11) 0.00527(14) 0.051(2) Uani 1 1 d . . .
C93 C 0.2046(3) 0.3939(10) 0.01541(14) 0.058(2) Uani 1 1 d . . .
C94 C 0.2116(3) 0.3751(10) 0.04116(15) 0.055(2) Uani 1 1 d . . .
F17 F 0.45826(13) 0.5754(5) 0.15979(7) 0.0455(10) Uani 1 1 d . . .
F18 F 0.55112(13) 0.5612(5) 0.15231(7) 0.0539(11) Uani 1 1 d . . .
F19 F 0.51315(13) 0.1935(5) 0.09149(7) 0.0531(11) Uani 1 1 d . . .
F20 F 0.42175(12) 0.1973(4) 0.10023(7) 0.0451(10) Uani 1 1 d . . .
F21 F 0.3036(2) 0.6273(6) 0.23429(9) 0.1002(19) Uani 1 1 d . . .
F22 F 0.3265(3) 0.6033(8) 0.28236(10) 0.136(3) Uani 1 1 d . . .
F23 F 0.3219(2) 0.0728(7) 0.27499(10) 0.111(2) Uani 1 1 d . . .
F24 F 0.2988(2) 0.0965(6) 0.22766(9) 0.0906(18) Uani 1 1 d . . .
F25 F 0.07301(16) 0.6880(6) 0.15380(12) 0.096(2) Uani 1 1 d . . .
F26 F -0.02170(17) 0.6714(6) 0.15566(13) 0.115(2) Uani 1 1 d . . .
F27 F -0.01139(16) 0.1343(6) 0.15541(13) 0.114(2) Uani 1 1 d . . .
F28 F 0.08290(16) 0.1538(6) 0.15400(12) 0.0962(19) Uani 1 1 d . . .
F29 F 0.2199(2) 0.7603(5) 0.05864(8) 0.0807(15) Uani 1 1 d . . .
F30 F 0.2062(2) 0.7976(6) 0.01139(8) 0.0870(16) Uani 1 1 d . . .
F31 F 0.1987(2) 0.2637(6) 0.00194(8) 0.1023(19) Uani 1 1 d . . .
F32 F 0.2140(2) 0.2297(6) 0.04944(8) 0.0897(17) Uani 1 1 d . . .
N5 N 0.28489(18) 0.8885(6) 0.13724(10) 0.0373(14) Uani 1 1 d . . .
N6 N 0.2218(2) 0.8859(7) 0.16426(10) 0.0437(15) Uani 1 1 d . . .
N7 N 0.23920(19) 1.1201(6) 0.14290(11) 0.0393(14) Uani 1 1 d . . .
N8 N 0.20090(18) 0.9060(6) 0.12111(10) 0.0344(14) Uani 1 1 d . . .
C45 C 0.2700(2) 0.8294(8) 0.15988(13) 0.0451(19) Uani 1 1 d . . .
H45A H 0.2694 0.7184 0.1593 0.054 Uiso 1 1 calc R . .
H45B H 0.2939 0.8602 0.1730 0.054 Uiso 1 1 calc R . .
C46 C 0.2854(2) 1.0579(8) 0.13900(13) 0.0418(18) Uani 1 1 d . . .
H46A H 0.3094 1.0884 0.1521 0.050 Uiso 1 1 calc R . .
H46B H 0.2958 1.1001 0.1242 0.050 Uiso 1 1 calc R . .
C47 C 0.2480(2) 0.8462(8) 0.11761(12) 0.0395(18) Uani 1 1 d . . .
H47A H 0.2461 0.7355 0.1165 0.047 Uiso 1 1 calc R . .
H47B H 0.2581 0.8845 0.1025 0.047 Uiso 1 1 calc R . .
C48 C 0.2247(3) 1.0565(9) 0.16479(13) 0.050(2) Uani 1 1 d . . .
H48A H 0.1928 1.0976 0.1676 0.061 Uiso 1 1 calc R . .
H48B H 0.2481 1.0878 0.1781 0.061 Uiso 1 1 calc R . .
C49 C 0.1872(2) 0.8452(9) 0.14414(14) 0.048(2) Uani 1 1 d . . .
H49A H 0.1549 0.8842 0.1469 0.057 Uiso 1 1 calc R . .
H49B H 0.1849 0.7346 0.1431 0.057 Uiso 1 1 calc R . .
C50 C 0.2051(2) 1.0724(9) 0.12277(13) 0.0444(19) Uani 1 1 d . . .
H50A H 0.2161 1.1119 0.1079 0.053 Uiso 1 1 calc R . .
H50B H 0.1730 1.1157 0.1245 0.053 Uiso 1 1 calc R . .
N13 N 0.71253(18) 0.4106(6) 0.10950(10) 0.0382(15) Uani 1 1 d . . .
N14 N 0.79623(19) 0.4125(7) 0.12633(10) 0.0391(15) Uani 1 1 d . . .
N15 N 0.75924(18) 0.6449(6) 0.10968(10) 0.0367(14) Uani 1 1 d . . .
N16 N 0.7767(2) 0.4348(7) 0.08316(10) 0.0433(15) Uani 1 1 d . . .
C95 C 0.7487(2) 0.3517(9) 0.12825(13) 0.0450(19) Uani 1 1 d . . .
H95A H 0.7499 0.2410 0.1271 0.054 Uiso 1 1 calc R . .
H95B H 0.7384 0.3774 0.1439 0.054 Uiso 1 1 calc R . .
C96 C 0.7132(2) 0.5783(8) 0.11201(15) 0.050(2) Uani 1 1 d . . .
H96A H 0.6893 0.6217 0.0998 0.060 Uiso 1 1 calc R . .
H96B H 0.7031 0.6049 0.1277 0.060 Uiso 1 1 calc R . .
C97 C 0.7283(2) 0.3729(9) 0.08595(13) 0.0461(19) Uani 1 1 d . . .
H97A H 0.7047 0.4139 0.0734 0.055 Uiso 1 1 calc R . .
H97B H 0.7290 0.2625 0.0841 0.055 Uiso 1 1 calc R . .
C98 C 0.7927(3) 0.5781(9) 0.12838(13) 0.048(2) Uani 1 1 d . . .
H98A H 0.7818 0.6034 0.1440 0.057 Uiso 1 1 calc R . .
H98B H 0.8251 0.6224 0.1277 0.057 Uiso 1 1 calc R . .
C99 C 0.7742(3) 0.5994(9) 0.08623(14) 0.054(2) Uani 1 1 d . . .
H99A H 0.8062 0.6431 0.0843 0.065 Uiso 1 1 calc R . .
H99B H 0.7510 0.6413 0.0736 0.065 Uiso 1 1 calc R . .
C100 C 0.8101(2) 0.3740(8) 0.10206(13) 0.0435(19) Uani 1 1 d . . .
H10A H 0.8428 0.4136 0.1004 0.052 Uiso 1 1 calc R . .
H10B H 0.8113 0.2635 0.1004 0.052 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
I1 C24 2.129(6) . ?
I2 C30 2.100(7) . ?
I3 C42 2.095(7) . ?
I4 C36 2.107(7) . ?
N1 C2 1.374(7) . ?
N1 C5 1.363(7) . ?
N1 H1 0.8600 . ?
N2 C10 1.382(7) . ?
N2 C7 1.382(7) . ?
N3 C12 1.322(7) . ?
N3 C15 1.344(7) . ?
N3 H3 0.8600 . ?
N4 C17 1.346(7) . ?
N4 C20 1.364(7) . ?
C1 C20 1.409(9) . ?
C1 C2 1.424(9) . ?
C1 C21 1.525(8) . ?
C2 C3 1.432(9) . ?
C3 C4 1.304(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.412(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(8) . ?
C6 C7 1.358(8) . ?
C6 C27 1.462(8) 2_665 ?
C7 C8 1.449(8) . ?
C8 C9 1.375(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.431(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(9) . ?
C11 C12 1.456(9) . ?
C11 C33 1.495(8) . ?
C12 C13 1.406(9) . ?
C13 C14 1.359(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(8) . ?
C16 C17 1.409(8) . ?
C16 C39 1.521(9) . ?
C17 C18 1.424(8) . ?
C18 C19 1.345(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.443(8) . ?
C19 H19 0.9300 . ?
C21 C22 1.360(9) . ?
C21 C26 1.411(9) . ?
C22 C23 1.291(8) . ?
C22 F1 1.365(7) . ?
C23 F2 1.358(7) . ?
C23 C24 1.400(10) . ?
C24 C25 1.359(9) . ?
C25 F3 1.345(7) . ?
C25 C26 1.316(8) . ?
C26 F4 1.358(7) . ?
C27 C28 1.348(10) . ?
C27 C32 1.358(10) . ?
C27 C6 1.462(8) 2_645 ?
C28 F5 1.344(8) . ?
C28 C29 1.386(10) . ?
C29 C30 1.336(10) . ?
C29 F6 1.392(9) . ?
C30 C31 1.378(11) . ?
C31 C32 1.386(10) . ?
C31 F7 1.352(9) . ?
C32 F8 1.342(8) . ?
C33 C38 1.368(10) . ?
C33 C34 1.377(10) . ?
C34 F9 1.341(8) . ?
C34 C35 1.318(10) . ?
C35 F10 1.322(9) . ?
C35 C36 1.368(11) 1_655 ?
C36 C35 1.368(11) 1_455 ?
C36 C37 1.354(11) 1_455 ?
C37 F11 1.333(9) . ?
C37 C38 1.340(9) . ?
C37 C36 1.354(11) 1_655 ?
C38 F12 1.344(8) . ?
C39 C44 1.366(10) . ?
C39 C40 1.348(10) . ?
C40 F13 1.343(9) . ?
C40 C41 1.366(11) . ?
C41 F14 1.348(10) . ?
C41 C42 1.352(12) 3_675 ?
C42 C41 1.352(12) 3_675 ?
C42 C43 1.406(12) 3_675 ?
C43 F15 1.352(10) . ?
C43 C42 1.406(12) 3_675 ?
C43 C44 1.360(11) . ?
C44 F16 1.342(9) . ?
I5 C74 2.142(6) . ?
I6 C80 2.061(8) . ?
I7 C86 2.103(7) . ?
I8 C92 2.098(7) 3_665 ?
N9 C55 1.330(7) . ?
N9 C52 1.367(7) . ?
N9 H9A 0.8600 . ?
N10 C60 1.335(7) . ?
N10 C57 1.361(7) . ?
N11 C65 1.374(8) . ?
N11 C62 1.377(7) . ?
N11 H11 0.8600 . ?
N12 C70 1.374(7) . ?
N12 C67 1.373(7) . ?
C51 C52 1.405(9) . ?
C51 C70 1.448(9) . ?
C51 C71 1.533(8) . ?
C52 C53 1.448(9) . ?
C53 C54 1.321(9) . ?
C53 H53 0.9300 . ?
C54 C55 1.460(9) . ?
C54 H54 0.9300 . ?
C55 C56 1.433(9) . ?
C56 C57 1.351(8) . ?
C56 C77 1.502(9) . ?
C57 C58 1.381(8) . ?
C58 C59 1.359(9) . ?
C58 H58 0.9300 . ?
C59 C60 1.400(8) . ?
C59 H59 0.9300 . ?
C60 C61 1.435(9) . ?
C61 C62 1.398(8) . ?
C61 C83 1.504(8) . ?
C62 C63 1.429(9) . ?
C63 C64 1.407(9) . ?
C63 H63 0.9300 . ?
C64 C65 1.450(8) . ?
C64 H64 0.9300 . ?
C65 C66 1.354(8) . ?
C66 C67 1.387(8) . ?
C66 C89 1.488(8) . ?
C67 C68 1.411(8) . ?
C68 C69 1.336(8) . ?
C68 H68 0.9300 . ?
C69 C70 1.449(9) . ?
C69 H69 0.9300 . ?
C71 C76 1.359(9) . ?
C71 C72 1.385(9) . ?
C72 F17 1.351(7) . ?
C72 C73 1.313(8) . ?
C73 F18 1.345(7) . ?
C73 C74 1.345(9) . ?
C74 C75 1.383(9) . ?
C75 C76 1.311(8) . ?
C75 F19 1.358(7) . ?
C76 F20 1.372(7) . ?
C77 C78 1.347(10) . ?
C77 C82 1.362(11) . ?
C78 F21 1.332(9) . ?
C78 C79 1.389(11) . ?
C79 F22 1.349(10) . ?
C79 C80 1.372(13) . ?
C80 C81 1.373(12) . ?
C81 F23 1.346(10) . ?
C81 C82 1.378(11) . ?
C82 F24 1.341(9) . ?
C83 C88 1.346(10) . ?
C83 C84 1.387(10) . ?
C84 F25 1.346(9) . ?
C84 C85 1.331(9) . ?
C85 C86 1.336(11) . ?
C85 F26 1.342(9) . ?
C86 C87 1.389(11) . ?
C87 F27 1.321(9) . ?
C87 C88 1.349(9) . ?
C88 F28 1.346(8) . ?
C89 C94 1.325(10) . ?
C89 C90 1.350(10) . ?
C90 F29 1.321(8) . ?
C90 C91 1.370(10) . ?
C91 C92 1.355(11) . ?
C91 F30 1.357(9) . ?
C92 C93 1.340(11) . ?
C92 I8 2.098(7) 3_665 ?
C93 F31 1.363(9) . ?
C93 C94 1.438(11) . ?
C94 F32 1.350(9) . ?
N5 C47 1.459(8) . ?
N5 C46 1.482(8) . ?
N5 C45 1.457(8) . ?
N6 C49 1.438(9) . ?
N6 C45 1.450(8) . ?
N6 C48 1.492(9) . ?
N7 C48 1.431(9) . ?
N7 C46 1.411(8) . ?
N7 C50 1.447(8) . ?
N8 C47 1.421(8) . ?
N8 C49 1.471(9) . ?
N8 C50 1.460(9) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
N13 C95 1.458(8) . ?
N13 C97 1.458(8) . ?
N13 C96 1.471(9) . ?
N14 C100 1.479(9) . ?
N14 C95 1.418(8) . ?
N14 C98 1.454(9) . ?
N15 C98 1.440(9) . ?
N15 C96 1.404(8) . ?
N15 C99 1.462(9) . ?
N16 C100 1.427(9) . ?
N16 C99 1.450(9) . ?
N16 C97 1.451(8) . ?
C95 H95A 0.9700 . ?
C95 H95B 0.9700 . ?
C96 H96A 0.9700 . ?
C96 H96B 0.9700 . ?
C97 H97A 0.9700 . ?
C97 H97B 0.9700 . ?
C98 H98A 0.9700 . ?
C98 H98B 0.9700 . ?
C99 H99A 0.9700 . ?
C99 H99B 0.9700 . ?
C100 H10A 0.9700 . ?
C100 H10B 0.9700 . ?

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
C2 N1 C5 105.7(5) . . ?
C2 N1 H1 127.1 . . ?
C5 N1 H1 127.1 . . ?
C10 N2 C7 109.0(5) . . ?
C12 N3 C15 106.9(5) . . ?
C12 N3 H3 126.6 . . ?
C15 N3 H3 126.6 . . ?
C17 N4 C20 108.0(5) . . ?
C20 C1 C2 125.4(6) . . ?
C20 C1 C21 118.0(5) . . ?
C2 C1 C21 116.6(6) . . ?
N1 C2 C1 123.7(6) . . ?
N1 C2 C3 109.2(5) . . ?
C1 C2 C3 127.1(6) . . ?
C4 C3 C2 106.8(6) . . ?
C4 C3 H3A 126.6 . . ?
C2 C3 H3A 126.6 . . ?
C3 C4 C5 109.2(6) . . ?
C3 C4 H4 125.4 . . ?
C5 C4 H4 125.4 . . ?
N1 C5 C4 109.1(5) . . ?
N1 C5 C6 124.7(5) . . ?
C4 C5 C6 126.1(6) . . ?
C7 C6 C5 127.2(6) . . ?
C7 C6 C27 117.6(5) . 2_665 ?
C5 C6 C27 115.1(5) . 2_665 ?
C6 C7 N2 126.2(5) . . ?
C6 C7 C8 125.6(6) . . ?
N2 C7 C8 107.9(5) . . ?
C9 C8 C7 106.7(6) . . ?
C9 C8 H8 126.7 . . ?
C7 C8 H8 126.7 . . ?
C8 C9 C10 108.7(5) . . ?
C8 C9 H9 125.6 . . ?
C10 C9 H9 125.6 . . ?
N2 C10 C11 126.7(5) . . ?
N2 C10 C9 107.6(6) . . ?
C11 C10 C9 125.7(6) . . ?
C10 C11 C12 124.8(6) . . ?
C10 C11 C33 116.8(6) . . ?
C12 C11 C33 118.4(6) . . ?
N3 C12 C13 109.9(6) . . ?
N3 C12 C11 125.4(6) . . ?
C13 C12 C11 124.8(6) . . ?
C14 C13 C12 106.9(6) . . ?
C14 C13 H13 126.6 . . ?
C12 C13 H13 126.6 . . ?
C13 C14 C15 105.6(6) . . ?
C13 C14 H14 127.2 . . ?
C15 C14 H14 127.2 . . ?
N3 C15 C16 125.4(5) . . ?
N3 C15 C14 110.7(5) . . ?
C16 C15 C14 123.8(6) . . ?
C15 C16 C17 127.2(6) . . ?
C15 C16 C39 116.6(5) . . ?
C17 C16 C39 116.2(5) . . ?
N4 C17 C16 125.5(5) . . ?
N4 C17 C18 109.0(5) . . ?
C16 C17 C18 125.5(6) . . ?
C19 C18 C17 108.1(6) . . ?
C19 C18 H18 126.0 . . ?
C17 C18 H18 126.0 . . ?
C18 C19 C20 106.3(6) . . ?
C18 C19 H19 126.9 . . ?
C20 C19 H19 126.9 . . ?
N4 C20 C1 126.0(5) . . ?
N4 C20 C19 108.5(5) . . ?
C1 C20 C19 125.5(6) . . ?
C22 C21 C26 113.3(5) . . ?
C22 C21 C1 125.2(6) . . ?
C26 C21 C1 121.5(6) . . ?
C23 C22 F1 117.8(6) . . ?
C23 C22 C21 125.3(6) . . ?
F1 C22 C21 116.9(5) . . ?
C22 C23 F2 120.2(6) . . ?
C22 C23 C24 120.5(6) . . ?
F2 C23 C24 119.4(5) . . ?
C25 C24 C23 116.7(6) . . ?
C25 C24 I1 123.1(5) . . ?
C23 C24 I1 120.2(5) . . ?
F3 C25 C26 119.1(6) . . ?
F3 C25 C24 119.6(6) . . ?
C26 C25 C24 121.3(6) . . ?
F4 C26 C25 117.7(6) . . ?
F4 C26 C21 119.4(5) . . ?
C25 C26 C21 122.9(6) . . ?
C28 C27 C32 115.6(6) . . ?
C28 C27 C6 122.2(6) . 2_645 ?
C32 C27 C6 122.1(6) . 2_645 ?
C27 C28 F5 121.5(6) . . ?
C27 C28 C29 120.9(7) . . ?
F5 C28 C29 117.6(8) . . ?
C30 C29 C28 124.7(7) . . ?
C30 C29 F6 118.1(7) . . ?
C28 C29 F6 117.1(7) . . ?
C29 C30 C31 114.5(7) . . ?
C29 C30 I2 124.6(6) . . ?
C31 C30 I2 120.6(6) . . ?
C32 C31 F7 118.9(8) . . ?
C32 C31 C30 121.0(7) . . ?
F7 C31 C30 120.0(7) . . ?
F8 C32 C27 119.1(7) . . ?
F8 C32 C31 117.6(7) . . ?
C27 C32 C31 123.2(7) . . ?
C38 C33 C34 114.4(6) . . ?
C38 C33 C11 123.0(7) . . ?
C34 C33 C11 122.6(6) . . ?
F9 C34 C35 118.4(7) . . ?
F9 C34 C33 117.6(6) . . ?
C35 C34 C33 124.1(7) . . ?
F10 C35 C34 119.8(7) . . ?
F10 C35 C36 120.4(7) . 1_655 ?
C34 C35 C36 119.7(8) . 1_655 ?
C35 C36 C37 118.3(7) 1_455 1_455 ?
C35 C36 I4 120.9(6) 1_455 . ?
C37 C36 I4 120.6(6) 1_455 . ?
F11 C37 C38 118.3(8) . . ?
F11 C37 C36 121.0(7) . 1_655 ?
C38 C37 C36 120.6(8) . 1_655 ?
F12 C38 C33 118.4(6) . . ?
F12 C38 C37 118.9(7) . . ?
C33 C38 C37 122.6(8) . . ?
C44 C39 C40 117.7(7) . . ?
C44 C39 C16 121.6(7) . . ?
C40 C39 C16 120.7(7) . . ?
F13 C40 C39 120.4(7) . . ?
F13 C40 C41 117.4(8) . . ?
C39 C40 C41 122.1(8) . . ?
F14 C41 C42 117.7(9) . 3_675 ?
F14 C41 C40 120.7(9) . . ?
C42 C41 C40 121.5(9) 3_675 . ?
C41 C42 C43 116.5(8) 3_675 3_675 ?
C41 C42 I3 124.0(7) 3_675 . ?
C43 C42 I3 119.3(7) 3_675 . ?
F15 C43 C42 119.9(8) . 3_675 ?
F15 C43 C44 119.1(9) . . ?
C42 C43 C44 121.0(9) 3_675 . ?
F16 C44 C39 120.7(6) . . ?
F16 C44 C43 118.1(8) . . ?
C39 C44 C43 121.1(8) . . ?
C55 N9 C52 104.4(5) . . ?
C55 N9 H9A 127.8 . . ?
C52 N9 H9A 127.8 . . ?
C60 N10 C57 107.8(5) . . ?
C65 N11 C62 107.5(5) . . ?
C65 N11 H11 126.3 . . ?
C62 N11 H11 126.3 . . ?
C70 N12 C67 107.3(5) . . ?
C52 C51 C70 124.2(6) . . ?
C52 C51 C71 119.8(5) . . ?
C70 C51 C71 116.1(6) . . ?
N9 C52 C51 124.6(5) . . ?
N9 C52 C53 111.6(5) . . ?
C51 C52 C53 123.8(6) . . ?
C54 C53 C52 105.6(6) . . ?
C54 C53 H53 127.2 . . ?
C52 C53 H53 127.2 . . ?
C53 C54 C55 106.7(6) . . ?
C53 C54 H54 126.6 . . ?
C55 C54 H54 126.6 . . ?
N9 C55 C54 111.6(5) . . ?
N9 C55 C56 124.7(6) . . ?
C54 C55 C56 123.7(6) . . ?
C57 C56 C55 126.9(6) . . ?
C57 C56 C77 117.5(6) . . ?
C55 C56 C77 115.6(6) . . ?
N10 C57 C56 125.6(6) . . ?
N10 C57 C58 108.6(5) . . ?
C56 C57 C58 125.6(6) . . ?
C59 C58 C57 107.8(6) . . ?
C59 C58 H58 126.1 . . ?
C57 C58 H58 126.1 . . ?
C58 C59 C60 106.4(6) . . ?
C58 C59 H59 126.8 . . ?
C60 C59 H59 126.8 . . ?
N10 C60 C59 109.3(5) . . ?
N10 C60 C61 125.9(6) . . ?
C59 C60 C61 124.8(6) . . ?
C62 C61 C60 124.9(5) . . ?
C62 C61 C83 116.8(5) . . ?
C60 C61 C83 118.2(6) . . ?
N11 C62 C63 111.4(6) . . ?
N11 C62 C61 125.5(6) . . ?
C63 C62 C61 123.1(6) . . ?
C62 C63 C64 104.7(6) . . ?
C62 C63 H63 127.6 . . ?
C64 C63 H63 127.6 . . ?
C63 C64 C65 108.0(6) . . ?
C63 C64 H64 126.0 . . ?
C65 C64 H64 126.0 . . ?
N11 C65 C66 126.3(5) . . ?
N11 C65 C64 108.4(6) . . ?
C66 C65 C64 125.3(6) . . ?
C65 C66 C67 126.5(6) . . ?
C65 C66 C89 117.8(5) . . ?
C67 C66 C89 115.7(5) . . ?
N12 C67 C68 109.5(5) . . ?
N12 C67 C66 125.1(6) . . ?
C68 C67 C66 125.3(6) . . ?
C69 C68 C67 107.8(6) . . ?
C69 C68 H68 126.1 . . ?
C67 C68 H68 126.1 . . ?
C68 C69 C70 107.8(6) . . ?
C68 C69 H69 126.1 . . ?
C70 C69 H69 126.1 . . ?
N12 C70 C51 125.3(6) . . ?
N12 C70 C69 107.6(5) . . ?
C51 C70 C69 127.1(6) . . ?
C76 C71 C72 115.1(6) . . ?
C76 C71 C51 123.3(6) . . ?
C72 C71 C51 121.6(6) . . ?
F17 C72 C73 118.5(6) . . ?
F17 C72 C71 119.2(6) . . ?
C73 C72 C71 122.3(7) . . ?
C72 C73 F18 119.2(6) . . ?
C72 C73 C74 121.3(6) . . ?
F18 C73 C74 119.5(6) . . ?
C73 C74 C75 117.8(6) . . ?
C73 C74 I5 121.6(5) . . ?
C75 C74 I5 120.5(5) . . ?
C76 C75 F19 119.0(6) . . ?
C76 C75 C74 119.9(7) . . ?
F19 C75 C74 121.1(6) . . ?
C75 C76 C71 123.4(6) . . ?
C75 C76 F20 117.0(6) . . ?
C71 C76 F20 119.6(5) . . ?
C78 C77 C82 115.9(7) . . ?
C78 C77 C56 121.5(7) . . ?
C82 C77 C56 122.5(7) . . ?
F21 C78 C77 119.2(7) . . ?
F21 C78 C79 117.9(9) . . ?
C77 C78 C79 122.9(9) . . ?
F22 C79 C80 117.5(9) . . ?
F22 C79 C78 120.5(10) . . ?
C80 C79 C78 122.0(9) . . ?
C79 C80 C81 114.3(8) . . ?
C79 C80 I6 121.5(8) . . ?
C81 C80 I6 124.2(8) . . ?
F23 C81 C80 117.8(8) . . ?
F23 C81 C82 118.9(9) . . ?
C80 C81 C82 123.3(9) . . ?
F24 C82 C77 120.3(7) . . ?
F24 C82 C81 117.9(8) . . ?
C77 C82 C81 121.6(8) . . ?
C88 C83 C84 115.4(6) . . ?
C88 C83 C61 122.7(6) . . ?
C84 C83 C61 121.8(7) . . ?
F25 C84 C85 119.4(7) . . ?
F25 C84 C83 118.7(6) . . ?
C85 C84 C83 121.9(8) . . ?
C86 C85 F26 120.9(7) . . ?
C86 C85 C84 122.0(8) . . ?
F26 C85 C84 117.1(8) . . ?
C85 C86 C87 118.1(7) . . ?
C85 C86 I7 122.6(6) . . ?
C87 C86 I7 119.2(6) . . ?
F27 C87 C86 122.2(7) . . ?
F27 C87 C88 118.9(8) . . ?
C86 C87 C88 118.8(8) . . ?
C83 C88 F28 119.6(6) . . ?
C83 C88 C87 123.9(7) . . ?
F28 C88 C87 116.5(7) . . ?
C94 C89 C90 117.6(6) . . ?
C94 C89 C66 119.0(7) . . ?
C90 C89 C66 123.2(6) . . ?
F29 C90 C89 120.2(7) . . ?
F29 C90 C91 118.0(7) . . ?
C89 C90 C91 121.8(7) . . ?
C92 C91 F30 118.8(7) . . ?
C92 C91 C90 122.4(8) . . ?
F30 C91 C90 118.7(7) . . ?
C93 C92 C91 116.2(7) . . ?
C93 C92 I8 120.9(7) . 3_665 ?
C91 C92 I8 122.7(6) . 3_665 ?
C92 C93 F31 121.9(7) . . ?
C92 C93 C94 121.3(8) . . ?
F31 C93 C94 116.8(8) . . ?
C89 C94 F32 122.9(7) . . ?
C89 C94 C93 120.6(8) . . ?
F32 C94 C93 116.5(8) . . ?
C47 N5 C46 107.7(5) . . ?
C47 N5 C45 109.2(5) . . ?
C46 N5 C45 107.4(5) . . ?
C49 N6 C45 108.9(6) . . ?
C49 N6 C48 106.9(6) . . ?
C45 N6 C48 107.3(5) . . ?
C48 N7 C46 108.1(6) . . ?
C48 N7 C50 109.7(5) . . ?
C46 N7 C50 106.7(5) . . ?
C47 N8 C49 107.5(5) . . ?
C47 N8 C50 107.9(5) . . ?
C49 N8 C50 109.2(5) . . ?
N6 C45 N5 111.1(5) . . ?
N6 C45 H45A 109.4 . . ?
N5 C45 H45A 109.4 . . ?
N6 C45 H45B 109.4 . . ?
N5 C45 H45B 109.4 . . ?
H45A C45 H45B 108.0 . . ?
N7 C46 N5 113.0(5) . . ?
N7 C46 H46A 109.0 . . ?
N5 C46 H46A 109.0 . . ?
N7 C46 H46B 109.0 . . ?
N5 C46 H46B 109.0 . . ?
H46A C46 H46B 107.8 . . ?
N5 C47 N8 111.8(5) . . ?
N5 C47 H47A 109.3 . . ?
N8 C47 H47A 109.3 . . ?
N5 C47 H47B 109.3 . . ?
N8 C47 H47B 109.3 . . ?
H47A C47 H47B 107.9 . . ?
N7 C48 N6 112.9(6) . . ?
N7 C48 H48A 109.0 . . ?
N6 C48 H48A 109.0 . . ?
N7 C48 H48B 109.0 . . ?
N6 C48 H48B 109.0 . . ?
H48A C48 H48B 107.8 . . ?
N6 C49 N8 112.7(5) . . ?
N6 C49 H49A 109.1 . . ?
N8 C49 H49A 109.1 . . ?
N6 C49 H49B 109.1 . . ?
N8 C49 H49B 109.1 . . ?
H49A C49 H49B 107.8 . . ?
N7 C50 N8 112.1(6) . . ?
N7 C50 H50A 109.2 . . ?
N8 C50 H50A 109.2 . . ?
N7 C50 H50B 109.2 . . ?
N8 C50 H50B 109.2 . . ?
H50A C50 H50B 107.9 . . ?
C95 N13 C97 109.0(5) . . ?
C95 N13 C96 106.4(5) . . ?
C97 N13 C96 108.0(6) . . ?
C100 N14 C95 107.7(5) . . ?
C100 N14 C98 108.8(5) . . ?
C95 N14 C98 107.3(5) . . ?
C98 N15 C96 106.0(6) . . ?
C98 N15 C99 108.8(5) . . ?
C96 N15 C99 107.6(6) . . ?
C100 N16 C99 108.4(6) . . ?
C100 N16 C97 107.8(5) . . ?
C99 N16 C97 107.6(6) . . ?
N13 C95 N14 112.0(6) . . ?
N13 C95 H95A 109.2 . . ?
N14 C95 H95A 109.2 . . ?
N13 C95 H95B 109.2 . . ?
N14 C95 H95B 109.2 . . ?
H95A C95 H95B 107.9 . . ?
N15 C96 N13 114.0(5) . . ?
N15 C96 H96A 108.8 . . ?
N13 C96 H96A 108.8 . . ?
N15 C96 H96B 108.8 . . ?
N13 C96 H96B 108.8 . . ?
H96A C96 H96B 107.7 . . ?
N13 C97 N16 111.4(5) . . ?
N13 C97 H97A 109.3 . . ?
N16 C97 H97A 109.3 . . ?
N13 C97 H97B 109.3 . . ?
N16 C97 H97B 109.3 . . ?
H97A C97 H97B 108.0 . . ?
N15 C98 N14 112.9(6) . . ?
N15 C98 H98A 109.0 . . ?
N14 C98 H98A 109.0 . . ?
N15 C98 H98B 109.0 . . ?
N14 C98 H98B 109.0 . . ?
H98A C98 H98B 107.8 . . ?
N15 C99 N16 113.3(6) . . ?
N15 C99 H99A 108.9 . . ?
N16 C99 H99A 108.9 . . ?
N15 C99 H99B 108.9 . . ?
N16 C99 H99B 108.9 . . ?
H99A C99 H99B 107.7 . . ?
N16 C100 N14 112.7(5) . . ?
N16 C100 H10A 109.1 . . ?
N14 C100 H10A 109.0 . . ?
N16 C100 H10B 109.0 . . ?
N14 C100 H10B 109.0 . . ?
H10A C100 H10B 107.8 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.315
_refine_diff_density_min         -1.165
_refine_diff_density_rms         0.176
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone, chloroform'
_database_code_depnum_ccdc_archive 'CCDC 1018108'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_smjl257s

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Hexamethylenetetramine 1,3,5-Trifluoro-2,4,6-tri-iodobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N4, C6 F3 I3'
_chemical_formula_sum            'C12 H12 F3 I3 N4'
_chemical_formula_weight         649.96

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'
I I -0.4742 1.8119 '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 1 m 1'
_symmetry_space_group_name_Hall  'P -2y'

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

_cell_length_a                   5.8849(13)
_cell_length_b                   24.903(3)
_cell_length_c                   6.2247(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.864(11)
_cell_angle_gamma                90.00
_cell_volume                     901.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    54
_cell_measurement_theta_min      5.4
_cell_measurement_theta_max      20.7

_exptl_crystal_description       parallelepipped
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    5.230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.447
_exptl_absorpt_correction_T_max  0.501
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;


_diffrn_ambient_temperature      250(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  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13934
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4952
_reflns_number_gt                4575
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0351P)²+0.7452P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.14(3)
_refine_ls_number_reflns         4952
_refine_ls_number_parameters     211
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_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
I1 I 0.10030(4) 0.636729(11) 0.68552(4) 0.03215(7) Uani 1 1 d . . .
I2 I 0.77798(6) 0.706812(13) 0.09748(6) 0.03957(9) Uani 1 1 d . . .
I3 I 0.52573(8) 0.858782(13) 0.77994(7) 0.05371(12) Uani 1 1 d . . .
F1 F 0.4199(7) 0.63766(12) 0.3135(6) 0.0474(8) Uani 1 1 d . . .
F2 F 0.7387(7) 0.81085(14) 0.3825(6) 0.0566(10) Uani 1 1 d . . .
F3 F 0.1943(7) 0.75922(14) 0.8178(6) 0.0542(9) Uani 1 1 d . . .
N1 N 0.6895(9) 0.95115(18) 0.0361(8) 0.0433(10) Uani 1 1 d . . .
N2 N 1.0511(14) 1.0000 0.1384(14) 0.0568(19) Uani 1 2 d S . .
N3 N 0.7561(15) 1.0000 0.3776(11) 0.0515(17) Uani 1 2 d S . .
N4 N 0.9147(11) 0.5000 0.2227(9) 0.0339(12) Uani 1 2 d S . .
N5 N 0.5575(10) 0.5000 -0.0372(11) 0.0416(14) Uani 1 2 d S . .
N6 N 0.8925(7) 0.54907(15) -0.1187(6) 0.0293(8) Uani 1 1 d . . .
C1 C 0.2988(9) 0.69737(19) 0.5666(8) 0.0322(10) Uani 1 1 d . . .
C2 C 0.4319(8) 0.68706(18) 0.4063(8) 0.0318(10) Uani 1 1 d . . .
C3 C 0.5769(10) 0.72465(19) 0.3355(8) 0.0341(10) Uani 1 1 d . . .
C4 C 0.5917(10) 0.7739(2) 0.4382(9) 0.0369(11) Uani 1 1 d . . .
C5 C 0.4628(11) 0.78688(19) 0.6020(8) 0.0385(11) Uani 1 1 d . . .
C6 C 0.3189(10) 0.74800(19) 0.6588(8) 0.0362(10) Uani 1 1 d . . .
C8 C 0.9375(13) 0.9523(3) 0.0319(12) 0.0547(15) Uani 1 1 d . . .
H8A H 0.9639 0.9513 -0.1180 0.066 Uiso 1 1 calc R . .
H8B H 1.0067 0.9204 0.1038 0.066 Uiso 1 1 calc R . .
C9 C 0.6543(13) 0.9520(2) 0.2652(10) 0.0505(14) Uani 1 1 d . . .
H9A H 0.4908 0.9512 0.2720 0.061 Uiso 1 1 calc R . .
H9B H 0.7232 0.9202 0.3382 0.061 Uiso 1 1 calc R . .
C10 C 0.5868(15) 1.0000 -0.0706(13) 0.0420(17) Uani 1 2 d S . .
H10A H 0.6091 1.0000 -0.2218 0.050 Uiso 1 2 calc SR . .
H10B H 0.4227 1.0000 -0.0668 0.050 Uiso 1 2 calc SR . .
C11 C 1.0056(19) 1.0000 0.3681(18) 0.063(3) Uani 1 2 d S . .
H11A H 1.0755 0.9685 0.4425 0.075 Uiso 0.50 1 calc PR . .
H11B H 1.0755 1.0315 0.4425 0.075 Uiso 0.50 1 calc PR . .
C12 C 0.6620(13) 0.5000 0.1936(12) 0.0422(17) Uani 1 2 d S . .
H12A H 0.6101 0.5315 0.2639 0.051 Uiso 0.50 1 calc PR . .
H12B H 0.6101 0.4685 0.2639 0.051 Uiso 0.50 1 calc PR . .
C13 C 0.9892(9) 0.45237(19) 0.1128(8) 0.0327(10) Uani 1 1 d . . .
H13A H 1.1558 0.4522 0.1278 0.039 Uiso 1 1 calc R . .
H13B H 0.9423 0.4203 0.1830 0.039 Uiso 1 1 calc R . .
C14 C 0.6389(9) 0.5478(2) -0.1393(9) 0.0387(11) Uani 1 1 d . . .
H14A H 0.5864 0.5796 -0.0719 0.046 Uiso 1 1 calc R . .
H14B H 0.5732 0.5483 -0.2921 0.046 Uiso 1 1 calc R . .
C15 C 0.9676(11) 0.5000 -0.2212(10) 0.0281(12) Uani 1 2 d S . .
H15A H 1.1339 0.5000 -0.2087 0.034 Uiso 1 2 calc SR . .
H15B H 0.9044 0.5000 -0.3747 0.034 Uiso 1 2 calc SR . .


_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
I1 C1 2.112(5) . ?
I2 C3 2.082(5) . ?
I3 C5 2.108(5) . ?
F1 C2 1.356(5) . ?
F2 C4 1.344(6) . ?
F3 C6 1.349(6) . ?
N1 C8 1.464(9) . ?
N1 C10 1.471(7) . ?
N1 C9 1.472(7) . ?
N2 C8 1.470(8) . ?
N2 C8 1.470(8) 2_575 ?
N2 C11 1.495(14) . ?
N3 C9 1.465(8) . ?
N3 C9 1.465(8) 2_575 ?
N3 C11 1.478(14) . ?
N4 C13 1.470(6) . ?
N4 C13 1.470(6) 2_565 ?
N4 C12 1.470(10) . ?
N5 C14 1.464(7) 2_565 ?
N5 C14 1.464(7) . ?
N5 C12 1.473(10) . ?
N6 C13 1.466(6) 2_565 ?
N6 C15 1.477(5) . ?
N6 C14 1.478(7) . ?
C1 C6 1.383(7) . ?
C1 C2 1.384(7) . ?
C2 C3 1.383(7) . ?
C3 C4 1.381(7) . ?
C4 C5 1.398(7) . ?
C5 C6 1.368(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N1 1.471(7) 2_575 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N6 1.466(6) 2_565 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N6 1.477(5) 2_565 ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
C8 N1 C10 108.5(5) . . ?
C8 N1 C9 107.8(5) . . ?
C10 N1 C9 108.4(5) . . ?
C8 N2 C8 107.8(8) . 2_575 ?
C8 N2 C11 107.2(5) . . ?
C8 N2 C11 107.2(5) 2_575 . ?
C9 N3 C9 109.3(7) . 2_575 ?
C9 N3 C11 108.4(5) . . ?
C9 N3 C11 108.4(5) 2_575 . ?
C13 N4 C13 107.6(5) . 2_565 ?
C13 N4 C12 108.2(4) . . ?
C13 N4 C12 108.2(4) 2_565 . ?
C14 N5 C14 108.7(6) 2_565 . ?
C14 N5 C12 108.0(4) 2_565 . ?
C14 N5 C12 108.0(4) . . ?
C13 N6 C15 107.9(4) 2_565 . ?
C13 N6 C14 108.6(4) 2_565 . ?
C15 N6 C14 108.0(4) . . ?
C6 C1 C2 116.5(4) . . ?
C6 C1 I1 121.5(3) . . ?
C2 C1 I1 121.7(3) . . ?
F1 C2 C3 118.2(4) . . ?
F1 C2 C1 118.5(4) . . ?
C3 C2 C1 123.3(4) . . ?
C4 C3 C2 116.9(4) . . ?
C4 C3 I2 121.1(4) . . ?
C2 C3 I2 121.9(3) . . ?
F2 C4 C3 119.1(5) . . ?
F2 C4 C5 118.3(5) . . ?
C3 C4 C5 122.7(5) . . ?
C6 C5 C4 116.9(4) . . ?
C6 C5 I3 122.1(4) . . ?
C4 C5 I3 120.5(4) . . ?
F3 C6 C5 118.1(4) . . ?
F3 C6 C1 118.2(4) . . ?
C5 C6 C1 123.7(5) . . ?
N1 C8 N2 113.2(5) . . ?
N1 C8 H8A 108.9 . . ?
N2 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
N2 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
N3 C9 N1 111.5(5) . . ?
N3 C9 H9A 109.3 . . ?
N1 C9 H9A 109.3 . . ?
N3 C9 H9B 109.3 . . ?
N1 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N1 C10 N1 111.6(7) 2_575 . ?
N1 C10 H10A 109.3 2_575 . ?
N1 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 2_575 . ?
N1 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
N3 C11 N2 111.3(8) . . ?
N3 C11 H11A 109.4 . . ?
N2 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
N2 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N4 C12 N5 112.5(6) . . ?
N4 C12 H12A 109.1 . . ?
N5 C12 H12A 109.1 . . ?
N4 C12 H12B 109.1 . . ?
N5 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
N6 C13 N4 112.2(4) 2_565 . ?
N6 C13 H13A 109.2 2_565 . ?
N4 C13 H13A 109.2 . . ?
N6 C13 H13B 109.2 2_565 . ?
N4 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N5 C14 N6 111.9(4) . . ?
N5 C14 H14A 109.2 . . ?
N6 C14 H14A 109.2 . . ?
N5 C14 H14B 109.2 . . ?
N6 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N6 C15 N6 111.6(5) . 2_565 ?
N6 C15 H15A 109.3 . . ?
N6 C15 H15A 109.3 2_565 . ?
N6 C15 H15B 109.3 . . ?
N6 C15 H15B 109.3 2_565 . ?
H15A C15 H15B 108.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.200
_refine_diff_density_min         -0.813
_refine_diff_density_rms         0.123
_exptl_crystal_recrystallization_method 
'exposing equimolar solutions of the respective XB donor and acceptor molecules in chloroform to a saturated atmosphere of n-pentane at room temperature. '
_database_code_depnum_ccdc_archive 'CCDC 1018109'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_smjl258p

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4-Diazabicyclo(2.2.2)octane 1,3,5-Trifluoro-2,4,6-tri-iodobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N2, C6 F3 I3'
_chemical_formula_sum            'C12 H12 F3 I3 N2'
_chemical_formula_weight         621.94

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_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                   6.2751(3)
_cell_length_b                   23.2198(11)
_cell_length_c                   11.8609(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.297(5)
_cell_angle_gamma                90.00
_cell_volume                     1681.88(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    138
_cell_measurement_theta_min      4.20
_cell_measurement_theta_max      22.21

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    5.596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2265
_exptl_absorpt_correction_T_max  0.8033
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_method       CCD
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14712
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4766
_reflns_number_gt                3526
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius BV, 1997-2000)'
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0504P)²+0.7540P] 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       0.0031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4766
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.24699(5) 0.130508(12) -0.09209(3) 0.03805(11) Uani 1 1 d . . .
I2 I -0.37070(5) 0.237760(15) 0.18078(3) 0.04287(12) Uani 1 1 d . . .
I3 I 0.11621(5) 0.387042(13) -0.09939(3) 0.04074(11) Uani 1 1 d . . .
F1 F -0.1036(5) 0.14513(11) 0.0701(3) 0.0459(7) Uani 1 1 d . . .
F2 F -0.1998(6) 0.34586(12) 0.0665(3) 0.0510(8) Uani 1 1 d . . .
F3 F 0.2729(5) 0.26269(12) -0.1405(3) 0.0507(9) Uani 1 1 d . . .
C1 C 0.0889(7) 0.20216(18) -0.0374(4) 0.0317(9) Uani 1 1 d . . .
C2 C -0.0566(7) 0.19765(18) 0.0342(4) 0.0320(10) Uani 1 1 d . . .
C3 C -0.1561(7) 0.24573(19) 0.0706(4) 0.0317(9) Uani 1 1 d . . .
C4 C -0.1034(7) 0.29895(18) 0.0325(4) 0.0323(10) Uani 1 1 d . . .
C5 C 0.0394(7) 0.30628(18) -0.0384(4) 0.0321(9) Uani 1 1 d . . .
C6 C 0.1324(7) 0.25717(19) -0.0709(4) 0.0328(10) Uani 1 1 d . . .
N1 N -0.5138(6) 0.04387(17) -0.1832(4) 0.0383(9) Uani 1 1 d . . .
N2 N -0.2895(7) -0.01906(16) -0.2915(4) 0.0361(9) Uani 1 1 d . . .
C7 C -0.3202(9) 0.0211(2) -0.1033(5) 0.0443(12) Uani 1 1 d . . .
H7A H -0.3652 -0.0032 -0.0452 0.09(2) Uiso 1 1 d R . .
H7B H -0.2320 0.0529 -0.0629 0.11(3) Uiso 1 1 d R . .
C8 C -0.1819(8) -0.0150(2) -0.1698(5) 0.0494(14) Uani 1 1 d . . .
H8A H -0.1596 -0.0537 -0.1363 0.055(17) Uiso 1 1 d R . .
H8B H -0.0380 0.0031 -0.1617 0.09(2) Uiso 1 1 d R . .
C9 C -0.4351(11) 0.0777(2) -0.2709(5) 0.0582(17) Uani 1 1 d . . .
H9A H -0.5601 0.0954 -0.3247 0.07(2) Uiso 1 1 d R . .
H9B H -0.3388 0.1087 -0.2326 0.07(2) Uiso 1 1 d R . .
C10 C -0.3095(11) 0.0391(2) -0.3394(6) 0.0590(17) Uani 1 1 d . . .
H10A H -0.1633 0.0551 -0.3348 0.07(2) Uiso 1 1 d R . .
H10B H -0.3871 0.0379 -0.4211 0.12(3) Uiso 1 1 d R . .
C11 C -0.6444(9) -0.0042(3) -0.2410(6) 0.0599(17) Uani 1 1 d . . .
H11A H -0.7688 0.0106 -0.2996 0.07(2) Uiso 1 1 d R . .
H11B H -0.7022 -0.0264 -0.1843 0.058(18) Uiso 1 1 d R . .
C12 C -0.5057(10) -0.0436(3) -0.2994(7) 0.070(2) Uani 1 1 d . . .
H12A H -0.4909 -0.0814 -0.2616 0.060(19) Uiso 1 1 d R . .
H12B H -0.5793 -0.0490 -0.3810 0.11(3) Uiso 1 1 d 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
I1 C1 2.114(4) . ?
I2 C3 2.089(4) . ?
I3 C5 2.105(4) . ?
F1 C2 1.347(5) . ?
F2 C4 1.352(5) . ?
F3 C6 1.346(5) . ?
C1 C6 1.383(6) . ?
C1 C2 1.386(6) . ?
C2 C3 1.395(6) . ?
C3 C4 1.382(6) . ?
C4 C5 1.373(6) . ?
C5 C6 1.376(6) . ?
N1 C7 1.457(6) . ?
N1 C11 1.460(7) . ?
N1 C9 1.478(7) . ?
N2 C8 1.449(7) . ?
N2 C12 1.454(6) . ?
N2 C10 1.458(7) . ?
C7 C8 1.546(6) . ?
C7 H7A 0.9801 . ?
C7 H7B 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9801 . ?
C9 C10 1.543(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 H10A 0.9801 . ?
C10 H10B 0.9800 . ?
C11 C12 1.532(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9799 . ?
C12 H12A 0.9802 . ?
C12 H12B 0.9800 . ?

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 C1 C2 116.5(4) . . ?
C6 C1 I1 120.1(3) . . ?
C2 C1 I1 123.4(3) . . ?
F1 C2 C1 119.0(4) . . ?
F1 C2 C3 118.7(4) . . ?
C1 C2 C3 122.3(4) . . ?
C4 C3 C2 117.2(4) . . ?
C4 C3 I2 121.4(3) . . ?
C2 C3 I2 121.4(3) . . ?
F2 C4 C5 118.9(4) . . ?
F2 C4 C3 117.8(4) . . ?
C5 C4 C3 123.4(4) . . ?
C4 C5 C6 116.6(4) . . ?
C4 C5 I3 123.7(3) . . ?
C6 C5 I3 119.8(3) . . ?
F3 C6 C5 118.2(4) . . ?
F3 C6 C1 117.7(4) . . ?
C5 C6 C1 124.1(4) . . ?
C7 N1 C11 108.7(4) . . ?
C7 N1 C9 106.7(4) . . ?
C11 N1 C9 108.6(5) . . ?
C8 N2 C12 107.7(4) . . ?
C8 N2 C10 107.8(5) . . ?
C12 N2 C10 110.0(5) . . ?
N1 C7 C8 110.3(4) . . ?
N1 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N1 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 C7 110.8(4) . . ?
N2 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.1 . . ?
N1 C9 C10 110.8(4) . . ?
N1 C9 H9A 109.5 . . ?
C10 C9 H9A 109.4 . . ?
N1 C9 H9B 109.5 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C9 110.0(4) . . ?
N2 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N2 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.1 . . ?
N1 C11 C12 110.6(4) . . ?
N1 C11 H11A 109.5 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N2 C12 C11 110.9(4) . . ?
N2 C12 H12A 109.4 . . ?
C11 C12 H12A 109.3 . . ?
N2 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.0 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.837
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.239
_exptl_crystal_recrystallization_method 
'exposing equimolar solutions of the respective XB donor and acceptor molecules in chloroform to a saturated atmosphere of n-pentane at room temperature.'
_database_code_depnum_ccdc_archive 'CCDC 1018110'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_smjl259sb

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,3,5-Trifluoro-2,4,6-tri-iodobenzene 4,4'-bipyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2, C6 F3 I3)'
_chemical_formula_sum            'C16 H8 F3 I3 N2'
_chemical_formula_weight         665.94

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'
I I -0.4742 1.8119 '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           monoclinic
_symmetry_space_group_name_H-M   'P n'
_symmetry_space_group_name_Hall  'P -2yac'

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

_cell_length_a                   4.1140(8)
_cell_length_b                   9.0710(9)
_cell_length_c                   24.104(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.621(19)
_cell_angle_gamma                90.00
_cell_volume                     899.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    30
_cell_measurement_theta_min      4.5
_cell_measurement_theta_max      13.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    5.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  0.819
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      250(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  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7515
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4736
_reflns_number_gt                3868
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0868P)²+0.2042P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.26(5)
_refine_ls_number_reflns         4736
_refine_ls_number_parameters     217
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1488
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.26096(14) 0.58102(9) 0.38837(3) 0.04130(18) Uani 1 1 d . . .
I2 I 0.88582(12) 0.53645(8) 0.16744(3) 0.04037(18) Uani 1 1 d . . .
I3 I 0.7529(2) 1.13389(8) 0.27649(4) 0.0560(2) Uani 1 1 d . . .
F1 F 0.5198(19) 0.4627(7) 0.2773(3) 0.0453(17) Uani 1 1 d . . .
F2 F 0.9220(19) 0.8845(8) 0.1908(3) 0.0509(17) Uani 1 1 d . . .
F3 F 0.425(2) 0.9221(8) 0.3626(3) 0.0525(18) Uani 1 1 d . . .
C1 C 0.469(3) 0.6901(11) 0.3208(4) 0.033(2) Uani 1 1 d . . .
C2 C 0.574(3) 0.6095(10) 0.2774(5) 0.0331(19) Uani 1 1 d . . .
C3 C 0.727(2) 0.6694(11) 0.2324(4) 0.0315(19) Uani 1 1 d . . .
C4 C 0.770(2) 0.8199(12) 0.2332(4) 0.033(2) Uani 1 1 d . . .
C5 C 0.673(2) 0.9074(10) 0.2765(4) 0.033(2) Uani 1 1 d . . .
C6 C 0.525(3) 0.8397(12) 0.3200(4) 0.036(2) Uani 1 1 d . . .
N1 N 0.552(3) 0.6397(13) -0.0311(5) 0.053(3) Uani 1 1 d . . .
N2 N 0.102(3) 1.3176(13) 0.0919(4) 0.044(2) Uani 1 1 d . . .
C7 C 0.452(4) 0.6477(13) 0.0213(6) 0.053(3) Uani 1 1 d . . .
H7 H 0.4407 0.5615 0.0421 0.064 Uiso 1 1 calc R . .
C8 C 0.366(4) 0.7794(13) 0.0455(5) 0.059(4) Uani 1 1 d . . .
H8 H 0.2943 0.7788 0.0818 0.071 Uiso 1 1 calc R . .
C9 C 0.382(3) 0.9089(13) 0.0184(4) 0.036(2) Uani 1 1 d . . .
C10 C 0.289(3) 1.0505(13) 0.0442(5) 0.041(3) Uani 1 1 d . . .
C11 C 0.347(4) 1.0781(13) 0.0988(5) 0.047(3) Uani 1 1 d . . .
H11 H 0.4463 1.0063 0.1210 0.057 Uiso 1 1 calc R . .
C12 C 0.261(4) 1.2109(15) 0.1218(5) 0.054(3) Uani 1 1 d . . .
H12 H 0.3131 1.2284 0.1591 0.065 Uiso 1 1 calc R . .
C13 C 0.047(3) 1.2927(14) 0.0385(4) 0.048(3) Uani 1 1 d . . .
H13 H -0.0566 1.3645 0.0169 0.058 Uiso 1 1 calc R . .
C14 C 0.140(4) 1.1628(14) 0.0141(5) 0.054(3) Uani 1 1 d . . .
H14 H 0.1006 1.1501 -0.0238 0.064 Uiso 1 1 calc R . .
C15 C 0.481(4) 0.9032(16) -0.0345(5) 0.055(3) Uani 1 1 d . . .
H15 H 0.4977 0.9897 -0.0550 0.066 Uiso 1 1 calc R . .
C16 C 0.560(5) 0.7658(18) -0.0590(6) 0.073(5) Uani 1 1 d . . .
H16 H 0.6192 0.7642 -0.0959 0.088 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
I1 C1 2.108(10) . ?
I2 C3 2.097(10) . ?
I3 C5 2.081(9) . ?
F1 C2 1.350(11) . ?
F2 C4 1.347(12) . ?
F3 C6 1.344(13) . ?
C1 C2 1.357(15) . ?
C1 C6 1.378(15) . ?
C2 C3 1.378(14) . ?
C3 C4 1.377(15) . ?
C4 C5 1.379(15) . ?
C5 C6 1.372(14) . ?
N1 C16 1.328(19) . ?
N1 C7 1.342(18) . ?
N2 C13 1.320(14) . ?
N2 C12 1.363(18) . ?
C7 C8 1.381(16) . ?
C7 H7 0.9300 . ?
C8 C9 1.347(16) . ?
C8 H8 0.9300 . ?
C9 C15 1.349(17) . ?
C9 C10 1.482(14) . ?
C10 C11 1.354(17) . ?
C10 C14 1.384(18) . ?
C11 C12 1.378(18) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.375(18) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.421(19) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.5(9) . . ?
C2 C1 I1 119.3(7) . . ?
C6 C1 I1 123.0(8) . . ?
F1 C2 C1 118.4(9) . . ?
F1 C2 C3 117.8(10) . . ?
C1 C2 C3 123.8(9) . . ?
C4 C3 C2 116.2(9) . . ?
C4 C3 I2 122.5(7) . . ?
C2 C3 I2 121.3(8) . . ?
F2 C4 C3 119.0(9) . . ?
F2 C4 C5 118.3(9) . . ?
C3 C4 C5 122.7(9) . . ?
C6 C5 C4 117.7(9) . . ?
C6 C5 I3 121.0(8) . . ?
C4 C5 I3 121.3(7) . . ?
F3 C6 C5 119.2(10) . . ?
F3 C6 C1 118.8(10) . . ?
C5 C6 C1 122.0(10) . . ?
C16 N1 C7 116.2(11) . . ?
C13 N2 C12 117.5(11) . . ?
N1 C7 C8 122.3(12) . . ?
N1 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C9 C8 C7 122.2(11) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C15 116.5(11) . . ?
C8 C9 C10 122.4(9) . . ?
C15 C9 C10 121.2(11) . . ?
C11 C10 C14 115.8(11) . . ?
C11 C10 C9 121.8(11) . . ?
C14 C10 C9 122.3(11) . . ?
C10 C11 C12 120.9(12) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
N2 C12 C11 122.1(12) . . ?
N2 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
N2 C13 C14 121.4(11) . . ?
N2 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C10 122.1(11) . . ?
C13 C14 H14 118.9 . . ?
C10 C14 H14 118.9 . . ?
C9 C15 C16 120.3(13) . . ?
C9 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
N1 C16 C15 122.5(12) . . ?
N1 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.851
_refine_diff_density_min         -2.286
_refine_diff_density_rms         0.282
_exptl_crystal_recrystallization_method 
'exposing equimolar solutions of the respective XB donor and acceptor molecules in chloroform to a saturated atmosphere of n-pentane at room temperature. '
_database_code_depnum_ccdc_archive 'CCDC 1018111'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_smjl1505

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4-Diazabicyclo(2.2.2)octane tetrafluoro-1,4-diiodobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N2, C6 F4 I2'
_chemical_formula_sum            'C12 H12 F4 I2 N2'
_chemical_formula_weight         514.04

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   6.8359(4)
_cell_length_b                   10.9401(6)
_cell_length_c                   11.4732(7)
_cell_angle_alpha                107.204(5)
_cell_angle_beta                 92.820(6)
_cell_angle_gamma                105.330(4)
_cell_volume                     782.88(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    87
_cell_measurement_theta_min      5.5
_cell_measurement_theta_max      20.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    4.049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;


_diffrn_ambient_temperature      250(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  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14490
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         29.99
_reflns_number_total             4547
_reflns_number_gt                3082
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0337P)²+0.0000P] 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       0.0127(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4547
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0756
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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
I1 I 1.24625(3) 0.44439(2) 0.23101(2) 0.03592(9) Uani 1 1 d . . .
I2 I 0.28664(3) 0.02319(2) 0.26611(2) 0.03605(9) Uani 1 1 d . . .
F1 F 1.0642(3) 0.3331(3) 0.4469(2) 0.0546(7) Uani 1 1 d . . .
F2 F 0.7021(3) 0.1770(2) 0.46141(18) 0.0491(6) Uani 1 1 d . . .
F3 F 0.4715(3) 0.1341(2) 0.05230(19) 0.0484(6) Uani 1 1 d . . .
F4 F 0.8374(3) 0.2855(2) 0.03630(19) 0.0498(6) Uani 1 1 d . . .
C1 C 0.9638(5) 0.3124(4) 0.2407(3) 0.0319(8) Uani 1 1 d . . .
C2 C 0.9206(5) 0.2827(4) 0.3466(3) 0.0322(8) Uani 1 1 d . . .
C3 C 0.7308(5) 0.2030(4) 0.3551(3) 0.0322(8) Uani 1 1 d . . .
C4 C 0.5743(5) 0.1498(3) 0.2575(3) 0.0297(8) Uani 1 1 d . . .
C5 C 0.6185(5) 0.1807(4) 0.1508(3) 0.0306(8) Uani 1 1 d . . .
C6 C 0.8082(5) 0.2578(4) 0.1425(3) 0.0310(8) Uani 1 1 d . . .
N1 N 0.5977(4) 0.6413(3) 0.2332(3) 0.0321(7) Uani 1 1 d . . .
N2 N 0.9192(4) 0.8356(3) 0.2599(3) 0.0319(7) Uani 1 1 d . . .
C7 C 0.6220(6) 0.7449(4) 0.3536(3) 0.0393(9) Uani 1 1 d . . .
H7A H 0.6284 0.7061 0.4190 0.047 Uiso 1 1 calc R . .
H7B H 0.5049 0.7796 0.3588 0.047 Uiso 1 1 calc R . .
C8 C 0.8195(6) 0.8594(4) 0.3696(3) 0.0409(9) Uani 1 1 d . . .
H8A H 0.7866 0.9434 0.3856 0.049 Uiso 1 1 calc R . .
H8B H 0.9120 0.8665 0.4397 0.049 Uiso 1 1 calc R . .
C9 C 0.5834(6) 0.7027(4) 0.1371(3) 0.0417(10) Uani 1 1 d . . .
H9A H 0.4637 0.7348 0.1415 0.050 Uiso 1 1 calc R . .
H9B H 0.5680 0.6365 0.0567 0.050 Uiso 1 1 calc R . .
C10 C 0.7780(6) 0.8207(4) 0.1534(3) 0.0386(9) Uani 1 1 d . . .
H10A H 0.8445 0.8043 0.0799 0.046 Uiso 1 1 calc R . .
H10B H 0.7404 0.9026 0.1651 0.046 Uiso 1 1 calc R . .
C11 C 0.7785(6) 0.5936(4) 0.2255(4) 0.0410(9) Uani 1 1 d . . .
H11A H 0.7643 0.5253 0.1465 0.049 Uiso 1 1 calc R . .
H11B H 0.7906 0.5539 0.2898 0.049 Uiso 1 1 calc R . .
C12 C 0.9728(6) 0.7104(4) 0.2402(4) 0.0401(9) Uani 1 1 d . . .
H12A H 1.0681 0.7190 0.3097 0.048 Uiso 1 1 calc R . .
H12B H 1.0391 0.6922 0.1667 0.048 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
I1 C1 2.114(3) . ?
I2 C4 2.111(3) . ?
F1 C2 1.349(4) . ?
F2 C3 1.344(4) . ?
F3 C5 1.351(4) . ?
F4 C6 1.351(3) . ?
C1 C2 1.374(5) . ?
C1 C6 1.380(5) . ?
C2 C3 1.385(4) . ?
C3 C4 1.380(5) . ?
C4 C5 1.389(4) . ?
C5 C6 1.372(4) . ?
N1 C11 1.460(5) . ?
N1 C9 1.462(4) . ?
N1 C7 1.474(4) . ?
N2 C8 1.449(4) . ?
N2 C10 1.461(4) . ?
N2 C12 1.467(5) . ?
C7 C8 1.540(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.548(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.542(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
C2 C1 C6 116.5(3) . . ?
C2 C1 I1 122.1(3) . . ?
C6 C1 I1 121.3(2) . . ?
F1 C2 C1 120.0(3) . . ?
F1 C2 C3 118.0(3) . . ?
C1 C2 C3 121.9(3) . . ?
F2 C3 C4 120.1(3) . . ?
F2 C3 C2 118.2(3) . . ?
C4 C3 C2 121.6(3) . . ?
C3 C4 C5 116.2(3) . . ?
C3 C4 I2 122.4(2) . . ?
C5 C4 I2 121.4(2) . . ?
F3 C5 C6 118.7(3) . . ?
F3 C5 C4 119.5(3) . . ?
C6 C5 C4 121.8(3) . . ?
F4 C6 C5 118.1(3) . . ?
F4 C6 C1 119.9(3) . . ?
C5 C6 C1 121.9(3) . . ?
C11 N1 C9 109.0(3) . . ?
C11 N1 C7 108.9(3) . . ?
C9 N1 C7 108.1(3) . . ?
C8 N2 C10 109.6(3) . . ?
C8 N2 C12 108.3(3) . . ?
C10 N2 C12 108.5(3) . . ?
N1 C7 C8 109.8(3) . . ?
N1 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N2 C8 C7 110.7(3) . . ?
N2 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N1 C9 C10 110.2(3) . . ?
N1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C9 110.0(3) . . ?
N2 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N1 C11 C12 110.3(3) . . ?
N1 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
N1 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N2 C12 C11 110.2(3) . . ?
N2 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.129
_exptl_crystal_recrystallization_method 
'exposing equimolar solutions of the respective XB donor and acceptor molecules in chloroform to a saturated atmosphere of n-pentane at room temperature. '
_database_code_depnum_ccdc_archive 'CCDC 1018112'
