#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:27:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180394 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/63/7206322.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7206322
loop_
_publ_author_name
'Davy, Karl J. P.'
'McMurtrie, John'
'Rintoul, Llew'
'Bernhardt, Paul V.'
'Micallef, Aaron S.'
_publ_section_title
;
 Vapour phase assembly of a halogen bonded complex of an isoindoline
 nitroxide and 1,2-diiodotetrafluorobenzene
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              5062
_journal_paper_doi               10.1039/c1ce05344b
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         '(C12 H16 N O)2, (C6 F4 I2)2'
_chemical_formula_sum            'C18 H16 F4 I2 N O'
_chemical_formula_weight         592.13
_chemical_melting_point          340
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.596(2)
_cell_angle_beta                 96.091(2)
_cell_angle_gamma                90.550(2)
_cell_formula_units_Z            4
_cell_length_a                   8.6551(2)
_cell_length_b                   12.9917(4)
_cell_length_c                   19.0093(4)
_cell_measurement_reflns_used    6658
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.9644
_cell_measurement_theta_min      2.8238
_cell_volume                     1999.99(9)
_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_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_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_molecular_graphics
;ORTEPIII (Farrugia, 1997)
WINGX-32 (Farrugia, 1999)
;
_computing_publication_material  'enCIFer 1.0 (CCDC, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0893
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18183
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.04
_diffrn_reflns_theta_min         2.83
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.187
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.93925
_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_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.967
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         9247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0010P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0392
_refine_ls_wR_factor_ref         0.0410
_reflns_number_gt                5540
_reflns_number_total             9247
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05344b.txt
_cod_data_source_block           TMIO2DITFB2
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7206322
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_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'
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_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_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) . . . . ?
