# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       a.micallef1@uq.edu.au
_publ_contact_author_name        'Aaron Micallef'
loop_
_publ_author_name
A.Micallef
K
Davy
'John McMurtrie'
L.Rintoul
P.Bernhardt

data_TMIO2DITFB2
_database_code_depnum_ccdc_archive 'CCDC 798433'
#TrackingRef 'web_deposit_cif_file_0_JohnMcMurtrie_1288135304.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          340
_chemical_formula_moiety         '(C12 H16 N O)2, (C6 F4 I2)2'
_chemical_formula_sum            'C36 H32 F8 I4 N2 O2'
_chemical_formula_weight         1184.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4740 1.8120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.6551(2)
_cell_length_b                   12.9917(4)
_cell_length_c                   19.0093(4)
_cell_angle_alpha                109.596(2)
_cell_angle_beta                 96.091(2)
_cell_angle_gamma                90.550(2)
_cell_volume                     1999.99(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6658
_cell_measurement_theta_min      2.8238
_cell_measurement_theta_max      28.9644

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.967
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1124
_exptl_absorpt_coefficient_mu    3.187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.93925
_exptl_absorpt_correction_T_max  1

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 16.0774
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18183
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0893
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         29.04
_reflns_number_total             9247
_reflns_number_gt                5540
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET)
(compiled Nov 29 2007,17:23:28)
;
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;ORTEPIII (Farrugia, 1997)
WINGX-32 (Farrugia, 1999)
;
_computing_publication_material  'enCIFer 1.0 (CCDC, 2003)'

_refine_special_details          
;
Refinement of F^2^ against ALL 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.
;

_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^)+(0.0010P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9247
_refine_ls_number_parameters     477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0410
_refine_ls_wR_factor_gt          0.0392
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_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
C1 C -0.2082(4) 0.5055(3) 0.0396(2) 0.0217(10) Uani 1 1 d . . .
C2 C -0.2807(5) 0.4578(3) -0.0326(2) 0.0236(11) Uani 1 1 d . . .
C3 C -0.2520(5) 0.3547(4) -0.0776(2) 0.0249(11) Uani 1 1 d . . .
C4 C -0.1435(5) 0.2967(3) -0.0509(2) 0.0260(11) Uani 1 1 d . . .
C5 C -0.0683(5) 0.3413(4) 0.0210(3) 0.0255(11) Uani 1 1 d . . .
C6 C -0.0984(4) 0.4443(3) 0.0673(2) 0.0235(11) Uani 1 1 d . . .
F1 F -0.3865(3) 0.51282(19) -0.06169(14) 0.0367(7) Uani 1 1 d . . .
F2 F -0.3244(3) 0.31041(19) -0.14713(13) 0.0369(7) Uani 1 1 d . . .
F3 F -0.1110(3) 0.19619(19) -0.09469(14) 0.0369(7) Uani 1 1 d . . .
F4 F 0.0346(3) 0.27982(19) 0.04496(14) 0.0368(7) Uani 1 1 d . . .
I1 I -0.25678(3) 0.66572(2) 0.100059(17) 0.03058(9) Uani 1 1 d . . .
I2 I 0.02242(3) 0.50259(3) 0.175496(17) 0.03206(9) Uani 1 1 d . . .
C7 C -0.1135(4) 0.8577(3) 0.4765(2) 0.0234(11) Uani 1 1 d . . .
C8 C -0.1118(5) 0.8728(4) 0.5507(3) 0.0264(11) Uani 1 1 d . . .
C9 C -0.1943(5) 0.9523(4) 0.5969(2) 0.0296(12) Uani 1 1 d . . .
C10 C -0.2827(5) 1.0187(4) 0.5683(3) 0.0304(12) Uani 1 1 d . . .
C11 C -0.2851(5) 1.0053(4) 0.4929(3) 0.0265(12) Uani 1 1 d . . .
C12 C -0.2034(5) 0.9263(3) 0.4460(2) 0.0242(11) Uani 1 1 d . . .
F5 F -0.0275(3) 0.8104(2) 0.58285(14) 0.0410(7) Uani 1 1 d . . .
F6 F -0.1906(3) 0.9635(2) 0.67032(14) 0.0491(8) Uani 1 1 d . . .
F7 F -0.3624(3) 1.0956(2) 0.61348(15) 0.0469(8) Uani 1 1 d . . .
F8 F -0.3728(3) 1.0735(2) 0.46800(14) 0.0421(7) Uani 1 1 d . . .
I3 I 0.02060(3) 0.73530(2) 0.412425(17) 0.03101(9) Uani 1 1 d . . .
I4 I -0.22417(4) 0.91174(3) 0.332441(17) 0.03493(9) Uani 1 1 d . . .
C13 C -0.2174(5) 1.0594(3) 0.1457(2) 0.0228(11) Uani 1 1 d . . .
C14 C -0.3318(5) 1.1412(3) 0.1363(2) 0.0204(10) Uani 1 1 d . . .
C15 C -0.2998(5) 1.2407(3) 0.1292(2) 0.0269(11) Uani 1 1 d . . .
H15 H -0.1953 1.2667 0.1328 0.032 Uiso 1 1 calc R . .
C16 C -0.4232(5) 1.3031(4) 0.1168(2) 0.0322(12) Uani 1 1 d . . .
H16 H -0.4025 1.3712 0.1105 0.039 Uiso 1 1 calc R . .
C17 C -0.5742(5) 1.2671(4) 0.1136(2) 0.0340(13) Uani 1 1 d . . .
H17 H -0.6568 1.3106 0.1051 0.041 Uiso 1 1 calc R . .
C18 C -0.6074(5) 1.1682(4) 0.1225(2) 0.0271(11) Uani 1 1 d . . .
H18 H -0.7120 1.1439 0.1210 0.033 Uiso 1 1 calc R . .
C19 C -0.4848(5) 1.1050(3) 0.1338(2) 0.0197(10) Uani 1 1 d . . .
C20 C -0.4951(5) 0.9958(3) 0.1440(2) 0.0236(11) Uani 1 1 d . . .
C21 C -0.0952(5) 1.1047(3) 0.2143(2) 0.0371(13) Uani 1 1 d . . .
H21A H -0.0349 1.0447 0.2213 0.056 Uiso 1 1 calc R . .
H21B H -0.1472 1.1397 0.2591 0.056 Uiso 1 1 calc R . .
H21C H -0.0254 1.1585 0.2064 0.056 Uiso 1 1 calc R . .
C22 C -0.1423(5) 1.0031(3) 0.0751(2) 0.0348(12) Uani 1 1 d . . .
H22A H -0.2233 0.9730 0.0325 0.052 Uiso 1 1 calc R . .
H22B H -0.0805 0.9437 0.0820 0.052 Uiso 1 1 calc R . .
H22C H -0.0746 1.0561 0.0649 0.052 Uiso 1 1 calc R . .
C23 C -0.5765(5) 0.9949(3) 0.2098(2) 0.0349(12) Uani 1 1 d . . .
H23A H -0.5271 1.0510 0.2556 0.052 Uiso 1 1 calc R . .
H23B H -0.5693 0.9229 0.2155 0.052 Uiso 1 1 calc R . .
H23C H -0.6861 1.0104 0.2011 0.052 Uiso 1 1 calc R . .
C24 C -0.5595(5) 0.9040(3) 0.0716(2) 0.0296(12) Uani 1 1 d . . .
H24A H -0.5520 0.8334 0.0796 0.044 Uiso 1 1 calc R . .
H24B H -0.4989 0.9041 0.0309 0.044 Uiso 1 1 calc R . .
H24C H -0.6686 0.9159 0.0581 0.044 Uiso 1 1 calc R . .
N1 N -0.3246(4) 0.9794(3) 0.15904(18) 0.0235(9) Uani 1 1 d . . .
O1 O -0.2766(3) 0.8981(2) 0.17557(15) 0.0326(8) Uani 1 1 d . . .
C25 C 0.4833(5) 0.5555(3) 0.3418(2) 0.0247(11) Uani 1 1 d . . .
C26 C 0.5660(5) 0.4602(3) 0.3544(2) 0.0213(11) Uani 1 1 d . . .
C27 C 0.7239(5) 0.4424(4) 0.3572(2) 0.0316(12) Uani 1 1 d . . .
H27 H 0.7948 0.4922 0.3488 0.038 Uiso 1 1 calc R . .
C28 C 0.7765(5) 0.3514(4) 0.3723(3) 0.0337(13) Uani 1 1 d . . .
H28 H 0.8845 0.3388 0.3741 0.040 Uiso 1 1 calc R . .
C29 C 0.6757(5) 0.2786(4) 0.3846(2) 0.0339(12) Uani 1 1 d . . .
H29 H 0.7145 0.2164 0.3949 0.041 Uiso 1 1 calc R . .
C30 C 0.5171(5) 0.2957(3) 0.3822(2) 0.0313(12) Uani 1 1 d . . .
H30 H 0.4466 0.2459 0.3908 0.038 Uiso 1 1 calc R . .
C31 C 0.4649(5) 0.3872(3) 0.3668(2) 0.0220(11) Uani 1 1 d . . .
C32 C 0.2991(5) 0.4198(3) 0.3620(2) 0.0235(11) Uani 1 1 d . . .
C33 C 0.5180(5) 0.6625(3) 0.4079(2) 0.0355(13) Uani 1 1 d . . .
H33A H 0.5068 0.6494 0.4550 0.053 Uiso 1 1 calc R . .
H33B H 0.4449 0.7169 0.4019 0.053 Uiso 1 1 calc R . .
H33C H 0.6246 0.6896 0.4090 0.053 Uiso 1 1 calc R . .
C34 C 0.5096(5) 0.5708(4) 0.2675(2) 0.0397(13) Uani 1 1 d . . .
H34A H 0.4494 0.6316 0.2617 0.060 Uiso 1 1 calc R . .
H34B H 0.4757 0.5036 0.2257 0.060 Uiso 1 1 calc R . .
H34C H 0.6204 0.5871 0.2676 0.060 Uiso 1 1 calc R . .
C35 C 0.2313(4) 0.4542(3) 0.4365(2) 0.0312(12) Uani 1 1 d . . .
H35A H 0.1307 0.4863 0.4310 0.047 Uiso 1 1 calc R . .
H35B H 0.3027 0.5083 0.4749 0.047 Uiso 1 1 calc R . .
H35C H 0.2168 0.3901 0.4517 0.047 Uiso 1 1 calc R . .
C36 C 0.1929(4) 0.3336(3) 0.2999(2) 0.0308(12) Uani 1 1 d . . .
H36A H 0.2380 0.3156 0.2523 0.046 Uiso 1 1 calc R . .
H36B H 0.0900 0.3627 0.2945 0.046 Uiso 1 1 calc R . .
H36C H 0.1830 0.2675 0.3134 0.046 Uiso 1 1 calc R . .
N2 N 0.3198(4) 0.5171(3) 0.33900(19) 0.0256(9) Uani 1 1 d . . .
O2 O 0.2054(3) 0.5701(2) 0.32379(16) 0.0321(8) Uani 1 1 d . . .

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
C1 0.019(2) 0.019(3) 0.030(3) 0.010(2) 0.007(2) 0.0010(19)
C2 0.019(3) 0.025(3) 0.032(3) 0.017(2) -0.001(2) 0.004(2)
C3 0.023(3) 0.025(3) 0.024(3) 0.007(2) -0.004(2) -0.006(2)
C4 0.034(3) 0.013(2) 0.032(3) 0.006(2) 0.015(2) 0.000(2)
C5 0.025(3) 0.025(3) 0.034(3) 0.020(2) 0.000(2) 0.004(2)
C6 0.026(3) 0.021(3) 0.027(3) 0.012(2) 0.006(2) -0.002(2)
F1 0.0368(16) 0.0317(16) 0.0421(17) 0.0169(14) -0.0075(13) 0.0046(13)
F2 0.0370(16) 0.0352(17) 0.0322(16) 0.0072(13) -0.0088(13) -0.0031(13)
F3 0.0369(16) 0.0240(16) 0.0438(17) 0.0037(13) 0.0047(13) 0.0037(13)
F4 0.0370(16) 0.0339(17) 0.0438(17) 0.0214(14) -0.0038(13) 0.0057(13)
I1 0.03233(19) 0.02296(19) 0.0354(2) 0.00758(16) 0.00667(15) 0.00383(15)
I2 0.03128(19) 0.0387(2) 0.02723(19) 0.01413(16) -0.00186(15) -0.00066(16)
C7 0.024(3) 0.019(3) 0.025(3) 0.004(2) 0.002(2) -0.004(2)
C8 0.026(3) 0.028(3) 0.030(3) 0.017(2) -0.002(2) 0.001(2)
C9 0.029(3) 0.043(3) 0.021(3) 0.016(2) 0.006(2) 0.000(2)
C10 0.026(3) 0.025(3) 0.037(3) 0.002(2) 0.012(2) 0.003(2)
C11 0.023(3) 0.024(3) 0.035(3) 0.014(2) -0.004(2) 0.004(2)
C12 0.023(3) 0.021(3) 0.026(3) 0.006(2) -0.002(2) -0.008(2)
F5 0.0422(17) 0.0499(19) 0.0396(17) 0.0264(15) 0.0036(14) 0.0163(14)
F6 0.0579(19) 0.066(2) 0.0311(17) 0.0235(16) 0.0161(14) 0.0176(15)
F7 0.0453(17) 0.0462(19) 0.0464(19) 0.0084(15) 0.0158(14) 0.0177(14)
F8 0.0441(17) 0.0412(18) 0.0482(18) 0.0246(15) 0.0036(14) 0.0185(13)
I3 0.02911(19) 0.02553(19) 0.0359(2) 0.00680(16) 0.00440(15) 0.00509(15)
I4 0.0426(2) 0.0368(2) 0.02667(19) 0.01410(16) -0.00186(16) 0.00201(16)
C13 0.025(3) 0.021(3) 0.021(3) 0.006(2) 0.001(2) 0.003(2)
C14 0.028(3) 0.019(3) 0.014(2) 0.005(2) 0.005(2) -0.001(2)
C15 0.028(3) 0.022(3) 0.028(3) 0.006(2) 0.004(2) -0.004(2)
C16 0.040(3) 0.021(3) 0.042(3) 0.017(2) 0.011(3) 0.004(2)
C17 0.041(3) 0.027(3) 0.039(3) 0.019(3) 0.002(3) 0.010(2)
C18 0.022(3) 0.037(3) 0.023(3) 0.011(2) 0.002(2) 0.005(2)
C19 0.023(3) 0.019(3) 0.012(2) 0.0010(19) -0.004(2) -0.002(2)
C20 0.020(3) 0.032(3) 0.019(3) 0.012(2) -0.006(2) -0.011(2)
C21 0.027(3) 0.034(3) 0.043(3) 0.006(3) -0.005(2) -0.004(2)
C22 0.038(3) 0.034(3) 0.042(3) 0.022(3) 0.015(2) 0.015(2)
C23 0.038(3) 0.036(3) 0.032(3) 0.011(2) 0.013(2) -0.003(2)
C24 0.033(3) 0.021(3) 0.028(3) -0.001(2) 0.001(2) -0.008(2)
N1 0.033(2) 0.020(2) 0.019(2) 0.0084(17) -0.0014(17) 0.0026(18)
O1 0.046(2) 0.0213(18) 0.0309(19) 0.0112(15) -0.0008(16) 0.0057(15)
C25 0.026(3) 0.024(3) 0.023(3) 0.007(2) -0.002(2) 0.003(2)
C26 0.024(3) 0.021(3) 0.018(2) 0.007(2) 0.001(2) 0.001(2)
C27 0.028(3) 0.032(3) 0.032(3) 0.006(2) 0.010(2) 0.000(2)
C28 0.023(3) 0.038(3) 0.041(3) 0.014(3) 0.003(2) 0.006(2)
C29 0.034(3) 0.034(3) 0.033(3) 0.010(2) 0.005(2) 0.013(2)
C30 0.034(3) 0.023(3) 0.036(3) 0.012(2) -0.007(2) -0.008(2)
C31 0.024(3) 0.018(3) 0.019(3) 0.001(2) 0.001(2) -0.001(2)
C32 0.020(3) 0.029(3) 0.019(3) 0.004(2) 0.000(2) -0.006(2)
C33 0.037(3) 0.022(3) 0.042(3) 0.005(2) -0.002(2) 0.001(2)
C34 0.053(3) 0.035(3) 0.037(3) 0.016(3) 0.018(3) 0.014(3)
C35 0.024(3) 0.039(3) 0.026(3) 0.004(2) 0.004(2) 0.002(2)
C36 0.022(3) 0.036(3) 0.029(3) 0.008(2) -0.007(2) -0.006(2)
N2 0.026(2) 0.024(2) 0.026(2) 0.0088(18) -0.0016(18) 0.0054(18)
O2 0.0327(18) 0.0292(19) 0.0297(19) 0.0039(15) 0.0019(15) 0.0145(15)

_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
C1 C2 1.379(5) . ?
C1 C6 1.415(5) . ?
C1 I1 2.084(4) . ?
C2 F1 1.351(4) . ?
C2 C3 1.368(5) . ?
C3 F2 1.333(4) . ?
C3 C4 1.370(5) . ?
C4 F3 1.344(4) . ?
C4 C5 1.378(5) . ?
C5 F4 1.345(4) . ?
C5 C6 1.378(5) . ?
C6 I2 2.094(4) . ?
C7 C8 1.357(5) . ?
C7 C12 1.414(5) . ?
C7 I3 2.096(4) . ?
C8 F5 1.346(4) . ?
C8 C9 1.373(6) . ?
C9 F6 1.350(5) . ?
C9 C10 1.365(6) . ?
C10 F7 1.332(5) . ?
C10 C11 1.383(6) . ?
C11 F8 1.343(4) . ?
C11 C12 1.372(6) . ?
C12 I4 2.091(4) . ?
C13 N1 1.488(5) . ?
C13 C14 1.500(5) . ?
C13 C22 1.516(6) . ?
C13 C21 1.531(5) . ?
C14 C15 1.373(5) . ?
C14 C19 1.391(5) . ?
C15 C16 1.395(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.371(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.498(5) . ?
C20 N1 1.504(5) . ?
C20 C23 1.501(6) . ?
C20 C24 1.533(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 O1 1.261(4) . ?
C25 N2 1.485(5) . ?
C25 C26 1.510(5) . ?
C25 C33 1.530(5) . ?
C25 C34 1.531(6) . ?
C26 C31 1.378(5) . ?
C26 C27 1.387(5) . ?
C27 C28 1.376(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.374(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.391(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.386(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.502(5) . ?
C32 N2 1.485(5) . ?
C32 C35 1.519(6) . ?
C32 C36 1.534(5) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
N2 O2 1.275(4) . ?

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 117.7(4) . . ?
C2 C1 I1 118.7(3) . . ?
C6 C1 I1 123.5(3) . . ?
F1 C2 C3 117.0(4) . . ?
F1 C2 C1 120.1(4) . . ?
C3 C2 C1 122.9(4) . . ?
F2 C3 C4 119.4(4) . . ?
F2 C3 C2 121.7(4) . . ?
C4 C3 C2 118.9(4) . . ?
F3 C4 C3 119.9(4) . . ?
F3 C4 C5 120.1(4) . . ?
C3 C4 C5 120.0(4) . . ?
F4 C5 C6 121.0(4) . . ?
F4 C5 C4 117.5(4) . . ?
C6 C5 C4 121.5(4) . . ?
C5 C6 C1 118.8(4) . . ?
C5 C6 I2 117.9(3) . . ?
C1 C6 I2 123.2(3) . . ?
C8 C7 C12 118.6(4) . . ?
C8 C7 I3 118.4(3) . . ?
C12 C7 I3 122.9(3) . . ?
F5 C8 C7 121.2(4) . . ?
F5 C8 C9 116.7(4) . . ?
C7 C8 C9 122.2(4) . . ?
F6 C9 C10 119.9(5) . . ?
F6 C9 C8 120.1(4) . . ?
C10 C9 C8 120.0(4) . . ?
F7 C10 C9 119.7(4) . . ?
F7 C10 C11 121.5(4) . . ?
C9 C10 C11 118.8(4) . . ?
F8 C11 C12 121.8(4) . . ?
F8 C11 C10 116.2(4) . . ?
C12 C11 C10 122.0(4) . . ?
C11 C12 C7 118.5(4) . . ?
C11 C12 I4 117.8(3) . . ?
C7 C12 I4 123.7(3) . . ?
N1 C13 C14 99.7(3) . . ?
N1 C13 C22 109.1(3) . . ?
C14 C13 C22 113.0(3) . . ?
N1 C13 C21 109.0(3) . . ?
C14 C13 C21 114.0(4) . . ?
C22 C13 C21 111.3(4) . . ?
C15 C14 C19 120.4(4) . . ?
C15 C14 C13 127.3(4) . . ?
C19 C14 C13 112.2(4) . . ?
C14 C15 C16 118.9(4) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 120.7(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.8(4) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 118.7(4) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C14 C19 C18 120.4(4) . . ?
C14 C19 C20 112.3(4) . . ?
C18 C19 C20 127.3(4) . . ?
C19 C20 N1 99.4(3) . . ?
C19 C20 C23 114.6(4) . . ?
N1 C20 C23 109.8(3) . . ?
C19 C20 C24 112.7(3) . . ?
N1 C20 C24 107.6(4) . . ?
C23 C20 C24 111.8(3) . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C22 H22A 109.5 . . ?
C13 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C13 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O1 N1 C13 122.5(3) . . ?
O1 N1 C20 122.0(3) . . ?
C13 N1 C20 115.3(3) . . ?
N2 C25 C26 99.4(3) . . ?
N2 C25 C33 109.0(4) . . ?
C26 C25 C33 113.0(3) . . ?
N2 C25 C34 110.2(3) . . ?
C26 C25 C34 113.5(4) . . ?
C33 C25 C34 111.1(4) . . ?
C31 C26 C27 119.7(4) . . ?
C31 C26 C25 111.9(4) . . ?
C27 C26 C25 128.3(4) . . ?
C28 C27 C26 119.0(4) . . ?
C28 C27 H27 120.5 . . ?
C26 C27 H27 120.5 . . ?
C27 C28 C29 121.3(4) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
C28 C29 C30 120.3(4) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 118.2(4) . . ?
C31 C30 H30 120.9 . . ?
C29 C30 H30 120.9 . . ?
C26 C31 C30 121.5(4) . . ?
C26 C31 C32 112.4(4) . . ?
C30 C31 C32 126.1(4) . . ?
N2 C32 C31 99.5(3) . . ?
N2 C32 C35 109.2(4) . . ?
C31 C32 C35 114.1(3) . . ?
N2 C32 C36 108.8(3) . . ?
C31 C32 C36 112.6(4) . . ?
C35 C32 C36 111.7(3) . . ?
C25 C33 H33A 109.5 . . ?
C25 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C25 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C25 C34 H34A 109.5 . . ?
C25 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C25 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C32 C36 H36A 109.5 . . ?
C32 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C32 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O2 N2 C25 121.6(3) . . ?
O2 N2 C32 122.4(4) . . ?
C25 N2 C32 115.7(3) . . ?

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
C6 C1 C2 F1 180.0(4) . . . . ?
I1 C1 C2 F1 -3.2(5) . . . . ?
C6 C1 C2 C3 0.7(6) . . . . ?
I1 C1 C2 C3 177.5(3) . . . . ?
F1 C2 C3 F2 0.3(6) . . . . ?
C1 C2 C3 F2 179.6(4) . . . . ?
F1 C2 C3 C4 178.9(4) . . . . ?
C1 C2 C3 C4 -1.8(7) . . . . ?
F2 C3 C4 F3 0.0(6) . . . . ?
C2 C3 C4 F3 -178.6(4) . . . . ?
F2 C3 C4 C5 -179.7(4) . . . . ?
C2 C3 C4 C5 1.7(7) . . . . ?
F3 C4 C5 F4 -1.2(6) . . . . ?
C3 C4 C5 F4 178.6(4) . . . . ?
F3 C4 C5 C6 179.7(4) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
F4 C5 C6 C1 -179.7(4) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
F4 C5 C6 I2 0.6(6) . . . . ?
C4 C5 C6 I2 179.6(3) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
I1 C1 C6 C5 -176.2(3) . . . . ?
C2 C1 C6 I2 -179.7(3) . . . . ?
I1 C1 C6 I2 3.6(5) . . . . ?
C12 C7 C8 F5 -179.6(3) . . . . ?
I3 C7 C8 F5 -0.5(5) . . . . ?
C12 C7 C8 C9 -0.1(6) . . . . ?
I3 C7 C8 C9 179.0(3) . . . . ?
F5 C8 C9 F6 -1.2(6) . . . . ?
C7 C8 C9 F6 179.3(4) . . . . ?
F5 C8 C9 C10 -179.9(3) . . . . ?
C7 C8 C9 C10 0.5(7) . . . . ?
F6 C9 C10 F7 1.3(6) . . . . ?
C8 C9 C10 F7 -180.0(4) . . . . ?
F6 C9 C10 C11 -179.8(4) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
F7 C10 C11 F8 -0.5(6) . . . . ?
C9 C10 C11 F8 -179.4(3) . . . . ?
F7 C10 C11 C12 180.0(4) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
F8 C11 C12 C7 179.9(3) . . . . ?
C10 C11 C12 C7 -0.6(6) . . . . ?
F8 C11 C12 I4 -1.7(5) . . . . ?
C10 C11 C12 I4 177.8(3) . . . . ?
C8 C7 C12 C11 0.1(6) . . . . ?
I3 C7 C12 C11 -178.9(3) . . . . ?
C8 C7 C12 I4 -178.2(3) . . . . ?
I3 C7 C12 I4 2.8(4) . . . . ?
N1 C13 C14 C15 173.5(4) . . . . ?
C22 C13 C14 C15 -70.8(5) . . . . ?
C21 C13 C14 C15 57.6(6) . . . . ?
N1 C13 C14 C19 -7.7(4) . . . . ?
C22 C13 C14 C19 108.0(4) . . . . ?
C21 C13 C14 C19 -123.6(4) . . . . ?
C19 C14 C15 C16 -2.2(6) . . . . ?
C13 C14 C15 C16 176.5(4) . . . . ?
C14 C15 C16 C17 1.6(7) . . . . ?
C15 C16 C17 C18 -0.1(7) . . . . ?
C16 C17 C18 C19 -0.9(7) . . . . ?
C15 C14 C19 C18 1.3(6) . . . . ?
C13 C14 C19 C18 -177.6(4) . . . . ?
C15 C14 C19 C20 -178.9(4) . . . . ?
C13 C14 C19 C20 2.2(5) . . . . ?
C17 C18 C19 C14 0.3(6) . . . . ?
C17 C18 C19 C20 -179.5(4) . . . . ?
C14 C19 C20 N1 4.3(4) . . . . ?
C18 C19 C20 N1 -175.9(4) . . . . ?
C14 C19 C20 C23 121.3(4) . . . . ?
C18 C19 C20 C23 -58.9(5) . . . . ?
C14 C19 C20 C24 -109.3(4) . . . . ?
C18 C19 C20 C24 70.5(6) . . . . ?
C14 C13 N1 O1 -174.8(3) . . . . ?
C22 C13 N1 O1 66.6(4) . . . . ?
C21 C13 N1 O1 -55.1(5) . . . . ?
C14 C13 N1 C20 11.0(4) . . . . ?
C22 C13 N1 C20 -107.6(4) . . . . ?
C21 C13 N1 C20 130.6(4) . . . . ?
C19 C20 N1 O1 175.9(3) . . . . ?
C23 C20 N1 O1 55.4(5) . . . . ?
C24 C20 N1 O1 -66.6(4) . . . . ?
C19 C20 N1 C13 -9.8(4) . . . . ?
C23 C20 N1 C13 -130.3(4) . . . . ?
C24 C20 N1 C13 107.7(4) . . . . ?
N2 C25 C26 C31 -7.1(4) . . . . ?
C33 C25 C26 C31 108.3(4) . . . . ?
C34 C25 C26 C31 -124.1(4) . . . . ?
N2 C25 C26 C27 175.3(4) . . . . ?
C33 C25 C26 C27 -69.3(6) . . . . ?
C34 C25 C26 C27 58.3(6) . . . . ?
C31 C26 C27 C28 0.1(6) . . . . ?
C25 C26 C27 C28 177.5(4) . . . . ?
C26 C27 C28 C29 -0.1(7) . . . . ?
C27 C28 C29 C30 -0.1(7) . . . . ?
C28 C29 C30 C31 0.2(6) . . . . ?
C27 C26 C31 C30 0.1(6) . . . . ?
C25 C26 C31 C30 -177.8(4) . . . . ?
C27 C26 C31 C32 179.7(4) . . . . ?
C25 C26 C31 C32 1.9(5) . . . . ?
C29 C30 C31 C26 -0.2(6) . . . . ?
C29 C30 C31 C32 -179.8(4) . . . . ?
C26 C31 C32 N2 4.3(4) . . . . ?
C30 C31 C32 N2 -176.1(4) . . . . ?
C26 C31 C32 C35 -111.8(4) . . . . ?
C30 C31 C32 C35 67.8(5) . . . . ?
C26 C31 C32 C36 119.5(4) . . . . ?
C30 C31 C32 C36 -60.9(6) . . . . ?
C26 C25 N2 O2 -175.1(3) . . . . ?
C33 C25 N2 O2 66.4(5) . . . . ?
C34 C25 N2 O2 -55.7(5) . . . . ?
C26 C25 N2 C32 10.5(4) . . . . ?
C33 C25 N2 C32 -108.0(4) . . . . ?
C34 C25 N2 C32 129.9(4) . . . . ?
C31 C32 N2 O2 176.1(3) . . . . ?
C35 C32 N2 O2 -64.1(4) . . . . ?
C36 C32 N2 O2 58.1(5) . . . . ?
C31 C32 N2 C25 -9.5(4) . . . . ?
C35 C32 N2 C25 110.3(4) . . . . ?
C36 C32 N2 C25 -127.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.867
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.114