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

#######################################################################
#
#                 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
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# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1-2I2_2PF6
_audit_creation_date             2014-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H36 I4 N4, 2(F6 P)'
_chemical_formula_sum            'C18 H36 F12 I4 N4 P2'
_chemical_formula_weight         1106.05
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H18 N4 F12 P2 I4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3275(5)
_cell_length_b                   8.5017(6)
_cell_length_c                   13.4868(9)
_cell_angle_alpha                84.830(6)
_cell_angle_beta                 86.312(6)
_cell_angle_gamma                74.381(6)
_cell_volume                     805.17(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3154
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      76.9079
_cell_measurement_theta_min      3.2932
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    32.151
_exptl_absorpt_correction_T_max  0.175
_exptl_absorpt_correction_T_min  0.037
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             522
_exptl_crystal_size_max          0.2328
_exptl_crystal_size_mid          0.1572
_exptl_crystal_size_min          0.1167
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5322
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.931
_diffrn_reflns_theta_min         3.293
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -110.00  -20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -30.0000  120.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  -60.0000 75

#__ type_ start__ end____ width___ exp.time_
  3 omega  -46.00   27.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   30.0000   90.0000 73

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       43.8187 -125.0000   60.0000 75

#__ type_ start__ end____ width___ exp.time_
  5 omega   29.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       43.8187  -99.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
  6 omega   43.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   77.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000  -60.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega   79.00  134.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000 -120.0000 55

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000  120.0000 72

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
 11 omega   49.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -30.0000 49

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 14 omega   73.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  178.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   52.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 16 omega  108.00  149.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  178.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
 17 omega   93.00  140.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
 18 omega   43.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
 19 omega   95.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000 -120.0000 83

#__ type_ start__ end____ width___ exp.time_
 20 omega   89.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -109.0000  175.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   53.00  148.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -15.0000 -120.0000 95

#__ type_ start__ end____ width___ exp.time_
 22 omega   45.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000 -120.0000 31
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1270839000
_diffrn_orient_matrix_UB_12      0.0965201000
_diffrn_orient_matrix_UB_13      0.0816740000
_diffrn_orient_matrix_UB_21      -0.0671315000
_diffrn_orient_matrix_UB_22      0.1471261000
_diffrn_orient_matrix_UB_23      -0.0765357000
_diffrn_orient_matrix_UB_31      -0.1645689000
_diffrn_orient_matrix_UB_32      -0.0681446000
_diffrn_orient_matrix_UB_33      -0.0254829000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2637
_reflns_number_total             2922
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         2.290
_refine_diff_density_min         -2.884
_refine_diff_density_rms         0.307
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2922
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0946P)²+11.5204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.1783
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F6A) \\sim Ueq, Uanis(F6B) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F3B)
\\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F4B) \\sim Ueq, Uanis(F5B) \\sim Ueq,
Uanis(F5A) \\sim Ueq: with sigma of 0.008 and sigma for terminal atoms of 0.012
3. Others
 Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=1-FVAR(1)
 Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.25445(9) 0.75890(8) 0.03275(5) 0.0203(2) Uani 1 1 d . . . . .
I2 I -0.52108(9) 0.74334(8) -0.10084(5) 0.0263(3) Uani 1 1 d . . . . .
N1 N -0.0146(12) 0.7749(11) 0.1543(6) 0.0181(18) Uani 1 1 d . . . . .
N2 N 0.2306(13) 0.7839(10) 0.2798(6) 0.0181(17) Uani 1 1 d . . . . .
C1 C 0.1329(16) 0.6199(13) 0.1597(8) 0.023(2) Uani 1 1 d . . . . .
H1A H 0.1985 0.6038 0.0951 0.027 Uiso 1 1 calc R . . . .
H1B H 0.0747 0.5305 0.1764 0.027 Uiso 1 1 calc R . . . .
C2 C 0.2763(18) 0.6174(14) 0.2383(10) 0.033(3) Uani 1 1 d . . . . .
H2A H 0.2701 0.5342 0.2915 0.039 Uiso 1 1 calc R . . . .
H2B H 0.4037 0.5913 0.2082 0.039 Uiso 1 1 calc R . . . .
C3 C 0.0750(15) 0.9085(13) 0.1220(8) 0.021(2) Uani 1 1 d . . . . .
H3A H -0.0204 1.0128 0.1211 0.025 Uiso 1 1 calc R . . . .
H3B H 0.1299 0.8938 0.0550 0.025 Uiso 1 1 calc R . . . .
C4 C 0.2305(17) 0.9096(15) 0.1930(8) 0.026(2) Uani 1 1 d . . . . .
H4A H 0.3532 0.8843 0.1577 0.032 Uiso 1 1 calc R . . . .
H4B H 0.2075 1.0175 0.2173 0.032 Uiso 1 1 calc R . . . .
C5 C -0.1088(15) 0.8072(13) 0.2544(7) 0.021(2) Uani 1 1 d . . . . .
H5A H -0.1677 0.7203 0.2773 0.025 Uiso 1 1 calc R . . . .
H5B H -0.2073 0.9096 0.2499 0.025 Uiso 1 1 calc R . . . .
C6 C 0.0377(15) 0.8167(15) 0.3301(7) 0.025(2) Uani 1 1 d . . . . .
H6A H 0.0040 0.9246 0.3553 0.030 Uiso 1 1 calc R . . . .
H6B H 0.0375 0.7365 0.3860 0.030 Uiso 1 1 calc R . . . .
C7 C 0.3803(15) 0.7803(13) 0.3523(8) 0.021(2) Uani 1 1 d . . . . .
H7A H 0.5039 0.7478 0.3183 0.025 Uiso 1 1 calc R . . . .
H7B H 0.3755 0.6973 0.4059 0.025 Uiso 1 1 calc R . . . .
C8 C 0.3617(16) 0.9444(14) 0.3981(8) 0.026(2) Uani 1 1 d . . . . .
H8A H 0.3758 1.0272 0.3460 0.031 Uiso 1 1 calc R . . . .
H8B H 0.2372 0.9810 0.4306 0.031 Uiso 1 1 calc R . . . .
C9 C 0.5122(15) 0.9215(13) 0.4727(8) 0.022(2) Uani 1 1 d . . . . .
H9A H 0.6362 0.8938 0.4388 0.026 Uiso 1 1 calc R . . . .
H9B H 0.5051 0.8314 0.5210 0.026 Uiso 1 1 calc R . . . .
P1 P 0.1640(4) 0.6653(3) 0.6546(2) 0.0225(6) Uani 1 1 d . . . . .
F2 F 0.0841(11) 0.7930(9) 0.5632(5) 0.0362(17) Uani 1 1 d . . . . .
F3 F 0.2422(10) 0.5381(8) 0.7471(5) 0.0332(16) Uani 1 1 d . . . . .
F3A F 0.269(4) 0.794(2) 0.6853(15) 0.044(5) Uani 0.58(4) 1 d . U P A 1
F3B F 0.180(5) 0.809(2) 0.7152(19) 0.037(6) Uani 0.42(4) 1 d . U P A 2
F4A F -0.013(3) 0.748(3) 0.7253(14) 0.048(6) Uani 0.58(4) 1 d . U P A 1
F4B F -0.048(3) 0.700(4) 0.697(2) 0.043(7) Uani 0.42(4) 1 d . U P A 2
F5A F 0.056(3) 0.543(2) 0.6217(15) 0.041(5) Uani 0.58(4) 1 d . U P A 1
F5B F 0.139(6) 0.516(4) 0.598(2) 0.057(8) Uani 0.42(4) 1 d . U P A 2
F6A F 0.336(3) 0.588(3) 0.5811(16) 0.052(6) Uani 0.58(4) 1 d . U P A 1
F6B F 0.375(4) 0.625(3) 0.615(2) 0.044(7) Uani 0.42(4) 1 d . U P A 2


_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 I2 2.7778(9) . ?
I1 N1 2.517(9) . ?
N1 C1 1.461(14) . ?
N1 C3 1.478(13) . ?
N1 C5 1.490(12) . ?
N2 C2 1.514(13) . ?
N2 C4 1.513(12) . ?
N2 C6 1.494(13) . ?
N2 C7 1.509(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.534(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.537(15) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.550(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.545(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.502(15) . ?
C9 C9 1.55(2) 2_676 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
P1 F2 1.597(7) . ?
P1 F3 1.603(7) . ?
P1 F3A 1.595(16) . ?
P1 F3B 1.57(2) . ?
P1 F4A 1.597(17) . ?
P1 F4B 1.58(2) . ?
P1 F5A 1.570(15) . ?
P1 F5B 1.60(3) . ?
P1 F6A 1.584(19) . ?
P1 F6B 1.56(2) . ?

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
N1 I1 I2 179.6(2) . . ?
C1 N1 I1 108.8(6) . . ?
C1 N1 C3 108.6(8) . . ?
C1 N1 C5 110.2(8) . . ?
C3 N1 I1 111.1(6) . . ?
C3 N1 C5 108.2(8) . . ?
C5 N1 I1 109.9(6) . . ?
C4 N2 C2 107.5(9) . . ?
C6 N2 C2 108.6(9) . . ?
C6 N2 C4 109.6(9) . . ?
C6 N2 C7 111.4(8) . . ?
C7 N2 C2 107.9(8) . . ?
C7 N2 C4 111.8(8) . . ?
N1 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
N1 C1 C2 111.3(9) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N2 C2 C1 109.2(9) . . ?
N2 C2 H2A 109.8 . . ?
N2 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 C4 110.6(8) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
N2 C4 C3 109.6(8) . . ?
N2 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
N1 C5 C6 110.4(8) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
N2 C6 C5 109.4(8) . . ?
N2 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 H7A 108.5 . . ?
N2 C7 H7B 108.5 . . ?
N2 C7 C8 114.9(9) . . ?
H7A C7 H7B 107.5 . . ?
C8 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 C7 109.4(9) . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C8 C9 C9 111.2(11) . 2_676 ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C9 C9 H9A 109.4 2_676 . ?
C9 C9 H9B 109.4 2_676 . ?
H9A C9 H9B 108.0 . . ?
F2 P1 F3 179.4(5) . . ?
F3A P1 F2 87.2(6) . . ?
F3A P1 F3 92.7(6) . . ?
F3A P1 F4A 88.6(11) . . ?
F3B P1 F2 90.0(8) . . ?
F3B P1 F3 89.7(8) . . ?
F3B P1 F4B 86.3(13) . . ?
F3B P1 F5B 176.5(15) . . ?
F4A P1 F2 91.4(7) . . ?
F4A P1 F3 88.0(7) . . ?
F4B P1 F2 86.5(9) . . ?
F4B P1 F3 93.0(9) . . ?
F4B P1 F5B 90.8(15) . . ?
F5A P1 F2 90.7(6) . . ?
F5A P1 F3 89.3(6) . . ?
F5A P1 F3A 177.9(8) . . ?
F5A P1 F4A 91.0(11) . . ?
F5A P1 F6A 88.8(11) . . ?
F5B P1 F2 91.7(11) . . ?
F5B P1 F3 88.6(11) . . ?
F6A P1 F2 86.5(8) . . ?
F6A P1 F3 94.2(8) . . ?
F6A P1 F3A 91.5(11) . . ?
F6A P1 F4A 177.8(9) . . ?
F6B P1 F2 95.1(10) . . ?
F6B P1 F3 85.4(10) . . ?
F6B P1 F3B 94.4(14) . . ?
F6B P1 F4B 178.2(12) . . ?
F6B P1 F5B 88.4(15) . . ?

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
I1 N1 C1 C2 -176.0(8) . . . . ?
I1 N1 C3 C4 -176.2(7) . . . . ?
I1 N1 C5 C6 179.8(7) . . . . ?
N1 C1 C2 N2 -5.1(13) . . . . ?
N1 C3 C4 N2 -5.5(12) . . . . ?
N1 C5 C6 N2 -2.2(12) . . . . ?
N2 C7 C8 C9 176.9(9) . . . . ?
C1 N1 C3 C4 -56.6(11) . . . . ?
C1 N1 C5 C6 59.9(11) . . . . ?
C2 N2 C4 C3 62.1(11) . . . . ?
C2 N2 C6 C5 -57.5(11) . . . . ?
C2 N2 C7 C8 176.9(10) . . . . ?
C3 N1 C1 C2 63.0(11) . . . . ?
C3 N1 C5 C6 -58.7(11) . . . . ?
C4 N2 C2 C1 -56.1(12) . . . . ?
C4 N2 C6 C5 59.6(11) . . . . ?
C4 N2 C7 C8 58.9(12) . . . . ?
C5 N1 C1 C2 -55.4(11) . . . . ?
C5 N1 C3 C4 63.0(11) . . . . ?
C6 N2 C2 C1 62.4(12) . . . . ?
C6 N2 C4 C3 -55.7(11) . . . . ?
C6 N2 C7 C8 -64.1(12) . . . . ?
C7 N2 C2 C1 -176.8(9) . . . . ?
C7 N2 C4 C3 -179.7(9) . . . . ?
C7 N2 C6 C5 -176.1(9) . . . . ?
C7 C8 C9 C9 -174.9(11) . . . 2_676 ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3 -3 4 0.1120 3.0000 -3.0000 4.0001 -0.3441 -0.9489 -0.3912
-4 -5 -1 0.0783 -4.0000 -5.0000 -1.0000 -0.0559 -0.3906 1.0245
-4 -3 -3 0.0740 -4.0000 -3.0000 -3.0000 -0.0262 0.0568 0.9392
3 5 0 0.0646 3.0000 5.0000 -0.0001 0.1013 0.5342 -0.8344
-1 1 9 0.0490 -1.0000 1.0000 9.0000 0.9587 -0.4746 -0.1329
4 2 -4 0.0813 4.0000 2.0000 -4.0000 -0.6420 0.3319 -0.6926
1 0 -8 0.0673 1.0000 -0.0000 -8.0000 -0.7805 0.5452 0.0393
4 3 4 0.0939 4.0000 3.0000 4.0000 0.1079 -0.1333 -0.9646
2 5 0 0.0731 2.0000 5.0000 -0.0001 0.2284 0.6014 -0.6699
-1 5 -2 0.0986 -1.0000 5.0000 -2.0001 0.4463 0.9558 -0.1252
3 -3 -1 0.0935 3.0000 -3.0000 -0.9999 -0.7525 -0.5662 -0.2638
-3 -5 -3 0.0794 -3.0000 -5.0000 -3.0000 -0.3464 -0.3046 0.9109
1 -1 -8 0.0656 1.0000 -1.0000 -8.0000 -0.8770 0.3980 0.1074
1 -1 8 0.0747 1.0000 -1.0000 8.0000 0.4298 -0.8265 -0.3003
1 2 -8 0.0673 1.0000 2.0000 -8.0000 -0.5874 0.8394 -0.0970
3 3 -4 0.0581 3.0000 3.0000 -4.0000 -0.4184 0.5461 -0.5962
-2 -2 7 0.0680 -2.0000 -2.0000 7.0000 0.6328 -0.6957 0.2870
-2 4 4 0.0787 -2.0000 4.0000 3.9999 0.9669 0.4166 -0.0454

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1023704'
#######################################################################
#
#                 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_1-2I2-I16_2-
_audit_creation_date             2014-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H36 N4, 2(I5), 5(I2)'
_chemical_formula_sum            'C18 H36 I20 N4'
_chemical_formula_weight         2846.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H36 N4 I20'
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2353(4)
_cell_length_b                   9.5741(4)
_cell_length_c                   15.2398(7)
_cell_angle_alpha                92.225(4)
_cell_angle_beta                 94.475(4)
_cell_angle_gamma                92.593(4)
_cell_volume                     1340.80(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5229
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      28.8410
_cell_measurement_theta_min      3.1440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    11.553
_exptl_absorpt_correction_T_max  0.206
_exptl_absorpt_correction_T_min  0.059
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic blackish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    3.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.1792
_exptl_crystal_size_min          0.1153
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8950
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         3.148
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -61.00   32.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -        9.5778  -57.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   50.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -        9.5778  -99.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   77.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -        9.5778   57.0000  -30.0000 95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0063286000
_diffrn_orient_matrix_UB_12      0.0267379000
_diffrn_orient_matrix_UB_13      0.0442653000
_diffrn_orient_matrix_UB_21      -0.0690381000
_diffrn_orient_matrix_UB_22      -0.0317071000
_diffrn_orient_matrix_UB_23      0.0064888000
_diffrn_orient_matrix_UB_31      0.0338006000
_diffrn_orient_matrix_UB_32      -0.0615600000
_diffrn_orient_matrix_UB_33      0.0134876000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4473
_reflns_number_total             5226
_reflns_odcompleteness_completeness 98.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.142
_refine_diff_density_min         -1.330
_refine_diff_density_rms         0.252
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         5226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0162P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0666
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.23215(5) 0.94876(4) 0.55762(3) 0.02011(12) Uani 1 1 d . . . . .
I2 I 0.27479(6) 1.09515(5) 0.71849(3) 0.02645(13) Uani 1 1 d . . . . .
N1 N 0.2062(6) 0.8234(5) 0.4077(4) 0.0184(14) Uani 1 1 d . . . . .
N2 N 0.1913(6) 0.7002(5) 0.2555(4) 0.0170(13) Uani 1 1 d . . . . .
C1 C 0.3454(9) 0.7639(7) 0.3933(5) 0.0250(18) Uani 1 1 d . . . . .
H1A H 0.3714 0.7022 0.4404 0.030 Uiso 1 1 calc R . . . .
H1B H 0.4203 0.8385 0.3945 0.030 Uiso 1 1 calc R . . . .
C2 C 0.3379(8) 0.6819(7) 0.3047(5) 0.0241(17) Uani 1 1 d . . . . .
H2A H 0.4150 0.7159 0.2702 0.029 Uiso 1 1 calc R . . . .
H2B H 0.3507 0.5834 0.3143 0.029 Uiso 1 1 calc R . . . .
C3 C 0.0917(8) 0.7115(7) 0.4016(5) 0.0202(16) Uani 1 1 d . . . . .
H3A H 0.0003 0.7503 0.4149 0.024 Uiso 1 1 calc R . . . .
H3B H 0.1155 0.6425 0.4447 0.024 Uiso 1 1 calc R . . . .
C4 C 0.0748(8) 0.6404(7) 0.3090(5) 0.0193(16) Uani 1 1 d . . . . .
H4A H 0.0838 0.5402 0.3130 0.023 Uiso 1 1 calc R . . . .
H4B H -0.0205 0.6565 0.2807 0.023 Uiso 1 1 calc R . . . .
C5 C 0.1709(9) 0.9266(7) 0.3402(5) 0.0229(18) Uani 1 1 d . . . . .
H5A H 0.2426 1.0042 0.3461 0.027 Uiso 1 1 calc R . . . .
H5B H 0.0763 0.9629 0.3483 0.027 Uiso 1 1 calc R . . . .
C6 C 0.1700(8) 0.8541(6) 0.2474(5) 0.0196(16) Uani 1 1 d . . . . .
H6A H 0.0781 0.8675 0.2142 0.023 Uiso 1 1 calc R . . . .
H6B H 0.2472 0.8957 0.2159 0.023 Uiso 1 1 calc R . . . .
C7 C 0.1918(7) 0.6242(7) 0.1664(4) 0.0171(15) Uani 1 1 d . . . . .
H7A H 0.2317 0.5334 0.1753 0.021 Uiso 1 1 calc R . . . .
H7B H 0.2571 0.6763 0.1313 0.021 Uiso 1 1 calc R . . . .
C8 C 0.0456(7) 0.6019(7) 0.1134(4) 0.0167(15) Uani 1 1 d . . . . .
H8A H 0.0040 0.6913 0.1020 0.020 Uiso 1 1 calc R . . . .
H8B H -0.0212 0.5471 0.1460 0.020 Uiso 1 1 calc R . . . .
C9 C 0.0705(7) 0.5241(7) 0.0260(5) 0.0208(17) Uani 1 1 d . . . . .
H9A H 0.1260 0.5856 -0.0095 0.025 Uiso 1 1 calc R . . . .
H9B H 0.1275 0.4434 0.0383 0.025 Uiso 1 1 calc R . . . .
I4 I 0.50927(5) 0.82555(5) 0.04490(3) 0.02511(13) Uani 1 1 d . . . . .
I5 I 0.61061(5) 0.57848(4) 0.11629(3) 0.01963(12) Uani 1 1 d . . . . .
I6 I 0.70786(5) 0.30574(5) 0.20121(3) 0.02182(12) Uani 1 1 d . . . . .
I8 I 0.05991(5) 0.23589(4) 0.22065(3) 0.02073(12) Uani 1 1 d . . . . .
I7 I 0.35835(5) 0.23635(5) 0.22103(3) 0.02220(12) Uani 1 1 d . . . . .
I9 I 0.71479(5) 0.48596(4) 0.38056(3) 0.02231(12) Uani 1 1 d . . . . .
I10 I 0.71005(6) 0.64385(5) 0.53628(4) 0.03098(14) Uani 1 1 d . . . . .
I3 I 0.13971(5) 1.03815(5) -0.01452(3) 0.02497(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.7680(7) . ?
I1 N1 2.528(6) . ?
N1 C1 1.458(10) . ?
N1 C3 1.466(8) . ?
N1 C5 1.482(8) . ?
N2 C2 1.516(9) . ?
N2 C4 1.506(8) . ?
N2 C6 1.503(8) . ?
N2 C7 1.517(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.531(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.537(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.550(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.520(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.540(11) . ?
C9 C9 1.514(12) 2_565 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
I4 I5 2.8100(6) . ?
I5 I6 3.0974(6) . ?
I8 I7 2.7555(7) . ?
I9 I10 2.7681(8) . ?
I3 I3 2.7241(10) 2_575 ?

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
N1 I1 I2 176.55(12) . . ?
C1 N1 I1 107.5(4) . . ?
C1 N1 C3 109.5(5) . . ?
C1 N1 C5 110.0(6) . . ?
C3 N1 I1 112.1(4) . . ?
C3 N1 C5 109.1(5) . . ?
C5 N1 I1 108.7(4) . . ?
C2 N2 C7 107.3(6) . . ?
C4 N2 C2 108.4(5) . . ?
C4 N2 C7 111.9(5) . . ?
C6 N2 C2 108.7(5) . . ?
C6 N2 C4 108.4(6) . . ?
C6 N2 C7 112.1(5) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 C2 110.9(6) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
N2 C2 C1 109.1(6) . . ?
N2 C2 H2A 109.9 . . ?
N2 C2 H2B 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N1 C3 H3A 109.4 . . ?
N1 C3 H3B 109.4 . . ?
N1 C3 C4 111.0(6) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
N2 C4 C3 108.8(5) . . ?
N2 C4 H4A 109.9 . . ?
N2 C4 H4B 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 H5A 109.9 . . ?
N1 C5 H5B 109.9 . . ?
N1 C5 C6 109.1(6) . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
N2 C6 C5 110.0(5) . . ?
N2 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 H7A 108.2 . . ?
N2 C7 H7B 108.2 . . ?
N2 C7 C8 116.4(6) . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
C7 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
C7 C8 C9 107.9(6) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C9 C9 C8 112.5(8) 2_565 . ?
C9 C9 H9A 109.1 2_565 . ?
C9 C9 H9B 109.1 2_565 . ?
H9A C9 H9B 107.8 . . ?
I4 I5 I6 176.86(2) . . ?

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
I1 N1 C1 C2 178.3(4) . . . . ?
I1 N1 C3 C4 178.1(4) . . . . ?
I1 N1 C5 C6 174.4(4) . . . . ?
N1 C1 C2 N2 5.5(7) . . . . ?
N1 C3 C4 N2 4.9(8) . . . . ?
N1 C5 C6 N2 5.2(8) . . . . ?
N2 C7 C8 C9 179.8(5) . . . . ?
C1 N1 C3 C4 -62.7(7) . . . . ?
C1 N1 C5 C6 57.0(7) . . . . ?
C2 N2 C4 C3 55.8(7) . . . . ?
C2 N2 C6 C5 -61.4(7) . . . . ?
C2 N2 C7 C8 167.4(5) . . . . ?
C3 N1 C1 C2 56.3(7) . . . . ?
C3 N1 C5 C6 -63.2(8) . . . . ?
C4 N2 C2 C1 -62.1(6) . . . . ?
C4 N2 C6 C5 56.2(7) . . . . ?
C4 N2 C7 C8 48.6(7) . . . . ?
C5 N1 C1 C2 -63.6(7) . . . . ?
C5 N1 C3 C4 57.7(8) . . . . ?
C6 N2 C2 C1 55.5(7) . . . . ?
C6 N2 C4 C3 -62.0(6) . . . . ?
C6 N2 C7 C8 -73.4(6) . . . . ?
C7 N2 C2 C1 176.9(5) . . . . ?
C7 N2 C4 C3 173.9(5) . . . . ?
C7 N2 C6 C5 -179.8(6) . . . . ?
C7 C8 C9 C9 170.9(6) . . . 2_565 ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
11 -1 -12 0.0684 11.0000 -1.0000 -12.0000 -0.4883 -0.8056 0.2715
3 10 -15 0.0719 3.0000 10.0000 -15.0000 -0.3776 -0.6215 -0.7165
9 -10 1 0.0950 9.0000 -10.0000 1.0000 -0.1662 -0.2978 0.9333
-8 -5 16 0.0342 -8.0000 -5.0000 16.0000 0.5239 0.8147 0.2532
-5 -4 -18 0.0917 -5.0000 -4.0000 -18.0000 -0.9354 0.3552 -0.1655
0 11 11 0.0521 -0.0000 11.0000 11.0000 0.7810 -0.2774 -0.5288
4 -13 -1 0.1072 4.0000 -13.0000 -1.0000 -0.3665 0.1296 0.9220
7 -10 10 0.0955 7.0000 -10.0000 10.0000 0.2196 -0.1013 0.9871
-9 6 -11 0.1566 -9.0000 6.0000 -11.0000 -0.3834 0.3597 -0.8219
2 5 -20 0.0675 2.0000 5.0000 -20.0000 -0.7390 -0.4264 -0.5100
5 -1 -20 0.0639 5.0000 -1.0000 -20.0000 -0.8804 -0.4433 -0.0392
13 1 -3 0.0794 13.0000 1.0000 -3.0000 -0.0238 -0.9487 0.3374

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1023705'
#######################################################################
#
#                 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_1-2I3-
_audit_creation_date             2014-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H36 N4, 2(I3)'
_chemical_formula_sum            'C18 H36 I6 N4'
_chemical_formula_weight         1069.91
_chemical_melting_point          ?
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'-x-1/2, y-1/2, z'
'x-1/2, -y-1/2, z'

_cell_length_a                   23.6028(6)
_cell_length_b                   25.1893(8)
_cell_length_c                   7.6207(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4530.8(2)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    298
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.183
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1190 before and 0.0760 after correction.
The Ratio of minimum to maximum transmission is 0.6895.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2940
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20815
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.617
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3267
_reflns_number_total             4796
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.007
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4796
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+20.7955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.1011
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 C19-C20
 1.54 with sigma of 0.02
 C20-C21
 1.54 with sigma of 0.02
 C21-C21_$3
 1.54 with sigma of 0.02
 N6-C19_$1
 1.5 with sigma of 0.02
 H20B_$1-H20A
 1.75 with sigma of 0.02
 C8-C9
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(I7B)=Sof(I8B)=Sof(I9B)=0.5*(1-FVAR(2))
 Sof(I7A)=Sof(I8A)=Sof(I9A)=0.5*FVAR(2)
 Fixed Sof: H1A(0.5) H1B(0.5) H2A(0.5) H2B(0.5) H5A(0.5) H5B(0.5) H6A(0.5)
 H6B(0.5) H7A(0.5) H7B(0.5) H8A(0.5) H8B(0.5) H9A(0.5) H9B(0.5) H10A(0.5)
 H10B(0.5) H11A(0.5) H11B(0.5) H12A(0.5) H12B(0.5) H17A(0.5) H17B(0.5)
 H18A(0.5) H18B(0.5) C19(0.5) H19A(0.5) H19B(0.5) C20(0.5) H20A(0.5) H20B(0.5)
 C21(0.5) H21A(0.5) H21B(0.5)
5.a Riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C8(H8A,H8B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B),
  C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2162(5) 0.5408(4) 0.5000 0.089(3) Uani 1 2 d S T P . .
N2 N 0.1541(4) 0.4578(3) 0.5000 0.053(2) Uani 1 2 d S T P . .
N3 N -0.1807(4) 0.1419(4) 0.5000 0.079(3) Uani 1 2 d S T P . .
N4 N -0.1307(4) 0.2322(3) 0.5000 0.059(2) Uani 1 2 d S T P . .
C1 C 0.2514(5) 0.4947(5) 0.5000 0.085(4) Uani 1 2 d S T P . .
H1A H 0.2755 0.4952 0.6029 0.102 Uiso 0.5 1 calc R . . . .
H1B H 0.2755 0.4952 0.3971 0.102 Uiso 0.5 1 calc R . . . .
C2 C 0.2170(4) 0.4443(4) 0.5000 0.058(3) Uani 1 2 d S T P . .
H2A H 0.2261 0.4234 0.6031 0.069 Uiso 0.5 1 calc R . . . .
H2B H 0.2261 0.4234 0.3969 0.069 Uiso 0.5 1 calc R . . . .
C3 C 0.1805(4) 0.5397(3) 0.3461(15) 0.107(4) Uani 1 1 d . . . . .
H3A H 0.2043 0.5398 0.2422 0.128 Uiso 1 1 calc R . . . .
H3B H 0.1575 0.5715 0.3438 0.128 Uiso 1 1 calc R . . . .
C4 C 0.1419(3) 0.4913(3) 0.3404(10) 0.071(2) Uani 1 1 d . . . . .
H4A H 0.1026 0.5024 0.3403 0.085 Uiso 1 1 calc R . . . .
H4B H 0.1490 0.4710 0.2345 0.085 Uiso 1 1 calc R . . . .
C5 C 0.1222(5) 0.4068(4) 0.5000 0.069(3) Uani 1 2 d S T P . .
H5A H 0.1339 0.3868 0.3975 0.083 Uiso 0.5 1 d R . . . .
H5B H 0.1339 0.3868 0.6025 0.083 Uiso 0.5 1 d R . . . .
C6 C 0.0592(5) 0.4102(4) 0.5000 0.076(3) Uani 1 2 d S T P . .
H6A H 0.0462 0.4290 0.3967 0.092 Uiso 0.5 1 calc R . . . .
H6B H 0.0462 0.4290 0.6033 0.092 Uiso 0.5 1 calc R . . . .
C7 C 0.0362(6) 0.3532(5) 0.5000 0.084(4) Uani 1 2 d S T P . .
H7A H 0.0508 0.3350 0.6028 0.101 Uiso 0.5 1 d R . . . .
H7B H 0.0508 0.3350 0.3972 0.101 Uiso 0.5 1 d R . . . .
C8 C -0.0263(6) 0.3503(5) 0.5000 0.094(4) Uani 1 2 d DS T P . .
H8A H -0.0414 0.3678 0.3967 0.113 Uiso 0.5 1 calc R . . . .
H8B H -0.0414 0.3678 0.6033 0.113 Uiso 0.5 1 calc R . . . .
C9 C -0.0438(5) 0.2901(4) 0.5000 0.077(3) Uani 1 2 d DS T P . .
H9A H -0.0288 0.2725 0.3967 0.092 Uiso 0.5 1 calc R . . . .
H9B H -0.0288 0.2725 0.6033 0.092 Uiso 0.5 1 calc R . . . .
C10 C -0.1053(5) 0.2875(4) 0.5000 0.076(3) Uani 1 2 d S T P . .
H10A H -0.1191 0.3063 0.3974 0.091 Uiso 0.5 1 calc R . . . .
H10B H -0.1191 0.3063 0.6026 0.091 Uiso 0.5 1 calc R . . . .
C11 C -0.2214(5) 0.1843(4) 0.5000 0.084(4) Uani 1 2 d S T P . .
H11A H -0.2454 0.1809 0.6028 0.100 Uiso 0.5 1 calc R . . . .
H11B H -0.2454 0.1809 0.3972 0.100 Uiso 0.5 1 calc R . . . .
C12 C -0.1948(4) 0.2389(4) 0.5000 0.061(3) Uani 1 2 d S T P . .
H12A H -0.2066 0.2585 0.6032 0.073 Uiso 0.5 1 calc R . . . .
H12B H -0.2066 0.2585 0.3968 0.073 Uiso 0.5 1 calc R . . . .
C13 C -0.1447(4) 0.1471(3) 0.6540(13) 0.092(3) Uani 1 1 d . . . . .
H13A H -0.1169 0.1187 0.6539 0.111 Uiso 1 1 calc R . . . .
H13B H -0.1677 0.1433 0.7587 0.111 Uiso 1 1 calc R . . . .
C14 C -0.1138(4) 0.2008(3) 0.6595(10) 0.072(2) Uani 1 1 d . . . . .
H14A H -0.1242 0.2200 0.7651 0.087 Uiso 1 1 calc R . . . .
H14B H -0.0732 0.1952 0.6602 0.087 Uiso 1 1 calc R . . . .
N5 N 0.1852(4) 0.2080(4) 0.5000 0.088(3) Uani 1 2 d S T P . .
N6 N 0.1090(4) 0.1379(4) 0.5000 0.084(3) Uani 1 2 d DS T P . .
C15 C 0.1479(5) 0.2101(5) 0.3444(17) 0.136(5) Uani 1 1 d . . . . .
H15A H 0.1308 0.2450 0.3375 0.164 Uiso 1 1 calc R . . . .
H15B H 0.1707 0.2051 0.2399 0.164 Uiso 1 1 calc R . . . .
C16 C 0.1030(5) 0.1702(4) 0.3466(15) 0.113(4) Uani 1 1 d . . . . .
H16A H 0.0663 0.1874 0.3472 0.136 Uiso 1 1 calc R . . . .
H16B H 0.1055 0.1482 0.2424 0.136 Uiso 1 1 calc R . . . .
C17 C 0.2115(5) 0.1562(4) 0.5000 0.078(3) Uani 1 2 d S T P . .
H17A H 0.2353 0.1527 0.6030 0.094 Uiso 0.5 1 calc R . . . .
H17B H 0.2353 0.1527 0.3970 0.094 Uiso 0.5 1 calc R . . . .
C18 C 0.1673(5) 0.1119(4) 0.5000 0.067(3) Uani 1 2 d S T P . .
H18A H 0.1717 0.0898 0.3967 0.080 Uiso 0.5 1 calc R . . . .
H18B H 0.1717 0.0898 0.6033 0.080 Uiso 0.5 1 calc R . . . .
C19 C 0.0624(8) 0.1001(6) 0.424(2) 0.106(7) Uani 0.5 1 d D U . . .
H19A H 0.0261 0.1181 0.4193 0.127 Uiso 0.5 1 calc R . . . .
H19B H 0.0724 0.0886 0.3067 0.127 Uiso 0.5 1 calc R . . . .
C20 C 0.0596(7) 0.0525(6) 0.5490(14) 0.093(6) Uani 0.5 1 d D U . . .
H20A H 0.0692 0.0645 0.6663 0.111 Uiso 0.5 1 calc DR . . . .
H20B H 0.0879 0.0268 0.5135 0.111 Uiso 0.5 1 calc DR . . . .
C21 C 0.0011(8) 0.0244(5) 0.556(2) 0.127(9) Uani 0.5 1 d D U . . .
H21A H -0.0073 0.0148 0.6766 0.152 Uiso 0.5 1 calc R . . . .
H21B H -0.0280 0.0490 0.5172 0.152 Uiso 0.5 1 calc R . . . .
I1 I 0.31622(5) 0.56461(3) 0.0000 0.0887(3) Uani 1 2 d S T P . .
I2 I 0.39539(4) 0.47458(3) 0.0000 0.0716(2) Uani 1 2 d S T P . .
I3 I 0.47210(4) 0.38391(4) 0.0000 0.0947(3) Uani 1 2 d S T P . .
I4 I 0.22998(4) 0.39931(4) 0.0000 0.0855(3) Uani 1 2 d S T P . .
I5 I 0.12782(4) 0.33235(3) 0.0000 0.0747(3) Uani 1 2 d S T P . .
I6 I 0.02913(4) 0.26303(4) 0.0000 0.0922(3) Uani 1 2 d S T P . .
I7A I 0.2736(3) 0.2313(3) 0.0000 0.0886(12) Uani 0.59(2) 2 d S T P A 1
I8A I 0.3638(5) 0.1509(2) 0.0000 0.0774(15) Uani 0.59(2) 2 d S T P A 1
I9A I 0.4519(5) 0.0702(2) 0.0000 0.1013(17) Uani 0.59(2) 2 d S T P A 1
I7B I 0.2876(6) 0.2092(8) 0.0000 0.105(3) Uani 0.41(2) 2 d S T P A 2
I8B I 0.3835(6) 0.1324(9) 0.0000 0.099(3) Uani 0.41(2) 2 d S T P A 2
I9B I 0.4718(6) 0.0548(8) 0.0000 0.130(3) Uani 0.41(2) 2 d S T P A 2


_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
N1 C1 1.428(15) . ?
N1 C3 1.444(11) 6_556 ?
N1 C3 1.444(11) . ?
N2 C2 1.524(13) . ?
N2 C4 1.507(8) . ?
N2 C4 1.507(8) 6_556 ?
N2 C5 1.489(12) . ?
N3 C11 1.437(14) . ?
N3 C13 1.455(10) . ?
N3 C13 1.455(10) 6_556 ?
N4 C10 1.518(13) . ?
N4 C12 1.522(13) . ?
N4 C14 1.503(8) . ?
N4 C14 1.503(8) 6_556 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.506(15) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.522(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9699 . ?
C5 H5B 0.9699 . ?
C5 C6 1.488(16) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.535(15) . ?
C7 H7A 0.9703 . ?
C7 H7B 0.9703 . ?
C7 C8 1.478(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.572(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.453(15) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.512(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.536(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N5 C15 1.478(13) 6_556 ?
N5 C15 1.478(13) . ?
N5 C17 1.445(13) . ?
N6 C16 1.430(11) 6_556 ?
N6 C16 1.430(11) . ?
N6 C18 1.524(14) . ?
N6 C19 1.566(14) . ?
N6 C19 1.566(14) 6_556 ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.459(14) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.527(14) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.532(14) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.553(15) . ?
C21 C21 1.500(17) 5_556 ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
I1 I2 2.9384(13) . ?
I2 I3 2.9145(13) . ?
I4 I5 2.9427(13) . ?
I5 I6 2.9112(14) . ?
I7A I8A 2.938(4) . ?
I8A I9A 2.907(5) . ?
I7B I8B 2.979(7) . ?
I8B I9B 2.857(7) . ?
I9B I9B 3.06(5) 5_655 ?

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
C1 N1 C3 108.8(7) . 6_556 ?
C1 N1 C3 108.8(7) . . ?
C3 N1 C3 108.6(11) 6_556 . ?
C4 N2 C2 108.1(5) 6_556 . ?
C4 N2 C2 108.1(5) . . ?
C4 N2 C4 107.6(7) 6_556 . ?
C5 N2 C2 107.4(8) . . ?
C5 N2 C4 112.7(5) . . ?
C5 N2 C4 112.7(5) . 6_556 ?
C11 N3 C13 108.9(6) . 6_556 ?
C11 N3 C13 108.9(6) . . ?
C13 N3 C13 107.5(10) . 6_556 ?
C10 N4 C12 106.8(8) . . ?
C14 N4 C10 112.3(5) 6_556 . ?
C14 N4 C10 112.3(5) . . ?
C14 N4 C12 108.8(6) 6_556 . ?
C14 N4 C12 108.8(6) . . ?
C14 N4 C14 107.9(8) 6_556 . ?
N1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
N1 C1 C2 111.9(10) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
N2 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
C1 C2 N2 109.6(8) . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 H3A 109.0 . . ?
N1 C3 H3B 109.0 . . ?
N1 C3 C4 112.9(8) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
N2 C4 C3 108.1(7) . . ?
N2 C4 H4A 110.1 . . ?
N2 C4 H4B 110.1 . . ?
C3 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
N2 C5 H5A 107.7 . . ?
N2 C5 H5B 107.7 . . ?
H5A C5 H5B 107.3 . . ?
C6 C5 N2 117.1(9) . . ?
C6 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
C5 C6 H6A 110.2 . . ?
C5 C6 H6B 110.2 . . ?
C5 C6 C7 107.5(10) . . ?
H6A C6 H6B 108.5 . . ?
C7 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
C6 C7 H7A 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 113.6(11) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
C7 C8 C9 108.1(11) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
C8 C9 H9A 110.2 . . ?
C8 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C10 C9 C8 107.8(11) . . ?
C10 C9 H9A 110.2 . . ?
C10 C9 H9B 110.2 . . ?
N4 C10 H10A 108.3 . . ?
N4 C10 H10B 108.3 . . ?
C9 C10 N4 115.8(10) . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
N3 C11 H11A 108.9 . . ?
N3 C11 H11B 108.9 . . ?
N3 C11 C12 113.4(10) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
N4 C12 H12A 110.1 . . ?
N4 C12 H12B 110.1 . . ?
C11 C12 N4 108.2(8) . . ?
C11 C12 H12A 110.1 . . ?
C11 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
N3 C13 H13A 109.2 . . ?
N3 C13 H13B 109.2 . . ?
N3 C13 C14 112.2(7) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
N4 C14 C13 108.4(7) . . ?
N4 C14 H14A 110.0 . . ?
N4 C14 H14B 110.0 . . ?
C13 C14 H14A 110.0 . . ?
C13 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C15 N5 C15 106.7(12) 6_556 . ?
C17 N5 C15 106.7(7) . 6_556 ?
C17 N5 C15 106.7(7) . . ?
C16 N6 C16 109.6(11) 6_556 . ?
C16 N6 C18 109.5(7) . . ?
C16 N6 C18 109.5(7) 6_556 . ?
C16 N6 C19 125.3(10) 6_556 . ?
C16 N6 C19 125.3(10) . 6_556 ?
C16 N6 C19 88.5(8) . . ?
C16 N6 C19 88.5(8) 6_556 6_556 ?
C18 N6 C19 111.8(10) . 6_556 ?
C18 N6 C19 111.8(10) . . ?
C19 N6 C19 43.3(13) . 6_556 ?
N5 C15 H15A 108.9 . . ?
N5 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 N5 113.5(9) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
N6 C16 C15 109.2(9) . . ?
N6 C16 H16A 109.8 . . ?
N6 C16 H16B 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
N5 C17 H17A 109.3 . . ?
N5 C17 H17B 109.3 . . ?
N5 C17 C18 111.5(10) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
N6 C18 C17 107.5(8) . . ?
N6 C18 H18A 110.2 . . ?
N6 C18 H18B 110.2 . . ?
C17 C18 H18A 110.2 . . ?
C17 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
N6 C19 H19A 110.5 . . ?
N6 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
C20 C19 N6 106.1(12) . . ?
C20 C19 H19A 110.5 . . ?
C20 C19 H19B 110.5 . . ?
C19 C20 H20A 108.6 . . ?
C19 C20 H20B 108.6 . . ?
C19 C20 C21 114.6(14) . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
C21 C21 C20 112.6(19) 5_556 . ?
C21 C21 H21A 109.1 5_556 . ?
C21 C21 H21B 109.1 5_556 . ?
H21A C21 H21B 107.8 . . ?
I3 I2 I1 178.92(4) . . ?
I6 I5 I4 178.11(4) . . ?
I9A I8A I7A 179.2(3) . . ?
I9B I8B I7B 177.4(4) . . ?
I8B I9B I9B 158.9(6) . 5_655 ?

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
N1 C1 C2 N2 0.0 . . . . ?
N1 C3 C4 N2 -1.2(11) . . . . ?
N2 C5 C6 C7 180.0 . . . . ?
N3 C11 C12 N4 0.0 . . . . ?
N3 C13 C14 N4 -0.1(11) . . . . ?
C1 N1 C3 C4 60.5(11) . . . . ?
C2 N2 C4 C3 -56.4(8) . . . . ?
C2 N2 C5 C6 180.0 . . . . ?
C3 N1 C1 C2 -59.1(6) . . . . ?
C3 N1 C1 C2 59.1(6) 6_556 . . . ?
C3 N1 C3 C4 -57.8(13) 6_556 . . . ?
C4 N2 C2 C1 -58.1(5) 6_556 . . . ?
C4 N2 C2 C1 58.1(5) . . . . ?
C4 N2 C4 C3 60.2(10) 6_556 . . . ?
C4 N2 C5 C6 -61.0(6) . . . . ?
C4 N2 C5 C6 61.0(6) 6_556 . . . ?
C5 N2 C2 C1 180.0 . . . . ?
C5 N2 C4 C3 -174.9(8) . . . . ?
C5 C6 C7 C8 180.0 . . . . ?
C6 C7 C8 C9 180.0 . . . . ?
C7 C8 C9 C10 180.0 . . . . ?
C8 C9 C10 N4 180.0 . . . . ?
C10 N4 C12 C11 180.0 . . . . ?
C10 N4 C14 C13 176.1(8) . . . . ?
C11 N3 C13 C14 -58.4(10) . . . . ?
C12 N4 C10 C9 180.0 . . . . ?
C12 N4 C14 C13 58.2(8) . . . . ?
C13 N3 C11 C12 -58.5(6) 6_556 . . . ?
C13 N3 C11 C12 58.5(6) . . . . ?
C13 N3 C13 C14 59.6(12) 6_556 . . . ?
C14 N4 C10 C9 -60.9(6) 6_556 . . . ?
C14 N4 C10 C9 60.9(6) . . . . ?
C14 N4 C12 C11 58.6(5) 6_556 . . . ?
C14 N4 C12 C11 -58.6(5) . . . . ?
C14 N4 C14 C13 -59.6(10) 6_556 . . . ?
N5 C15 C16 N6 -2.2(15) . . . . ?
N5 C17 C18 N6 0.0 . . . . ?
N6 C19 C20 C21 152.4(12) . . . . ?
C15 N5 C15 C16 -52.7(16) 6_556 . . . ?
C15 N5 C17 C18 56.9(7) 6_556 . . . ?
C15 N5 C17 C18 -56.9(7) . . . . ?
C16 N6 C16 C15 61.8(15) 6_556 . . . ?
C16 N6 C18 C17 60.1(7) . . . . ?
C16 N6 C18 C17 -60.1(7) 6_556 . . . ?
C16 N6 C19 C20 173.7(13) . . . . ?
C16 N6 C19 C20 -73.1(16) 6_556 . . . ?
C17 N5 C15 C16 61.1(12) . . . . ?
C18 N6 C16 C15 -58.3(11) . . . . ?
C18 N6 C19 C20 63.3(13) . . . . ?
C19 N6 C16 C15 164.5(11) 6_556 . . . ?
C19 N6 C16 C15 -171.0(12) . . . . ?
C19 N6 C18 C17 -156.6(7) 6_556 . . . ?
C19 N6 C18 C17 156.6(7) . . . . ?
C19 N6 C19 C20 -35.9(14) 6_556 . . . ?
C19 C20 C21 C21 99(2) . . . 5_556 ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1023706'
#######################################################################
#
#                 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_1-I4_2-
_audit_creation_date             2014-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H36 N4, 4(I)'
_chemical_formula_sum            'C18 H36 I4 N4'
_chemical_formula_weight         816.11
_chemical_melting_point          ?
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   28.9478(14)
_cell_length_b                   14.3498(9)
_cell_length_c                   6.3034(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2618.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    123
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.771
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1336 before and 0.0809 after correction.
The Ratio of minimum to maximum transmission is 0.6164.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            15764
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.153
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2399
_reflns_number_total             2638
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         3.538
_refine_diff_density_min         -1.137
_refine_diff_density_rms         0.221
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2638
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.198
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+44.2980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1497
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2857(2) 0.0108(5) -0.4757(11) 0.0240(15) Uani 1 1 d . . . . .
N2 N 0.3732(2) 0.0064(5) -0.4002(10) 0.0173(13) Uani 1 1 d . . . . .
C1 C 0.2983(3) -0.0759(7) -0.3730(14) 0.0271(19) Uani 1 1 d . . . . .
H1A H 0.2942 -0.1280 -0.4742 0.033 Uiso 1 1 calc R . . . .
H1B H 0.2775 -0.0868 -0.2509 0.033 Uiso 1 1 calc R . . . .
C2 C 0.3496(3) -0.0740(6) -0.2935(12) 0.0217(17) Uani 1 1 d . . . . .
H2A H 0.3505 -0.0661 -0.1375 0.026 Uiso 1 1 calc R . . . .
H2B H 0.3652 -0.1331 -0.3301 0.026 Uiso 1 1 calc R . . . .
C3 C 0.2994(3) 0.0888(7) -0.3395(14) 0.0285(19) Uani 1 1 d . . . . .
H3A H 0.2858 0.0802 -0.1967 0.034 Uiso 1 1 calc R . . . .
H3B H 0.2871 0.1476 -0.3991 0.034 Uiso 1 1 calc R . . . .
C4 C 0.3528(3) 0.0960(6) -0.3198(13) 0.0235(17) Uani 1 1 d . . . . .
H4A H 0.3644 0.1492 -0.4048 0.028 Uiso 1 1 calc R . . . .
H4B H 0.3618 0.1061 -0.1699 0.028 Uiso 1 1 calc R . . . .
C5 C 0.3133(3) 0.0186(6) -0.6760(13) 0.0248(18) Uani 1 1 d . . . . .
H5A H 0.3095 0.0819 -0.7360 0.030 Uiso 1 1 calc R . . . .
H5B H 0.3014 -0.0267 -0.7812 0.030 Uiso 1 1 calc R . . . .
C6 C 0.3639(3) 0.0002(6) -0.6370(12) 0.0194(16) Uani 1 1 d . . . . .
H6A H 0.3829 0.0468 -0.7134 0.023 Uiso 1 1 calc R . . . .
H6B H 0.3723 -0.0625 -0.6899 0.023 Uiso 1 1 calc R . . . .
C7 C 0.4253(2) 0.0037(6) -0.3662(13) 0.0210(17) Uani 1 1 d . . . . .
H7A H 0.4390 0.0605 -0.4293 0.025 Uiso 1 1 calc R . . . .
H7B H 0.4380 -0.0507 -0.4430 0.025 Uiso 1 1 calc R . . . .
C8 C 0.4399(3) -0.0024(6) -0.1332(12) 0.0231(17) Uani 1 1 d . . . . .
H8A H 0.4256 0.0494 -0.0526 0.028 Uiso 1 1 calc R . . . .
H8B H 0.4289 -0.0618 -0.0719 0.028 Uiso 1 1 calc R . . . .
C9 C 0.4916(2) 0.0030(6) -0.1131(12) 0.0224(18) Uani 1 1 d . U . . .
H9A H 0.5023 0.0625 -0.1755 0.027 Uiso 1 1 calc R . . . .
H9B H 0.5055 -0.0483 -0.1960 0.027 Uiso 1 1 calc R . . . .
I1 I 0.39088(4) 0.2500 0.16579(14) 0.0387(3) Uani 1 2 d S T P . .
I2 I 0.48811(4) 0.2500 0.46226(18) 0.0439(3) Uani 1 2 d S T P . .
I3 I 0.57152(3) 0.2500 0.69280(17) 0.0405(3) Uani 1 2 d S T P . .
I4 I 0.67696(3) 0.2500 0.88839(14) 0.0316(3) Uani 1 2 d S T P . .


_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
N1 C1 1.449(11) . ?
N1 C3 1.464(11) . ?
N1 C5 1.498(10) . ?
N2 C2 1.500(10) . ?
N2 C4 1.503(10) . ?
N2 C6 1.519(9) . ?
N2 C7 1.523(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.567(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.557(11) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.510(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.531(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.502(10) . ?
C9 C9 1.510(16) 5_655 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
I2 I3 2.8180(15) . ?

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
C1 N1 C3 109.0(7) . . ?
C1 N1 C5 107.9(7) . . ?
C3 N1 C5 107.1(7) . . ?
C2 N2 C4 109.2(6) . . ?
C2 N2 C6 108.4(6) . . ?
C2 N2 C7 111.7(6) . . ?
C4 N2 C6 108.2(6) . . ?
C4 N2 C7 111.2(6) . . ?
C6 N2 C7 108.1(6) . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N1 C1 C2 111.5(7) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N2 C2 C1 107.6(6) . . ?
N2 C2 H2A 110.2 . . ?
N2 C2 H2B 110.2 . . ?
C1 C2 H2A 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
N1 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
N1 C3 C4 111.5(7) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
N2 C4 C3 107.8(7) . . ?
N2 C4 H4A 110.2 . . ?
N2 C4 H4B 110.2 . . ?
C3 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
N1 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
N1 C5 C6 111.5(6) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
N2 C6 H6A 109.9 . . ?
N2 C6 H6B 109.9 . . ?
C5 C6 N2 108.7(6) . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 H7A 108.7 . . ?
N2 C7 H7B 108.7 . . ?
N2 C7 C8 114.3(6) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 C7 110.7(6) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C8 C9 C9 113.5(8) . 5_655 ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C9 C9 H9A 108.9 5_655 . ?
C9 C9 H9B 108.9 5_655 . ?
H9A C9 H9B 107.7 . . ?

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
N1 C1 C2 N2 -15.2(9) . . . . ?
N1 C3 C4 N2 -14.5(10) . . . . ?
N1 C5 C6 N2 -15.8(10) . . . . ?
N2 C7 C8 C9 -175.5(7) . . . . ?
C1 N1 C3 C4 66.8(9) . . . . ?
C1 N1 C5 C6 -49.1(9) . . . . ?
C2 N2 C4 C3 -50.7(8) . . . . ?
C2 N2 C6 C5 68.0(8) . . . . ?
C2 N2 C7 C8 -53.9(9) . . . . ?
C3 N1 C1 C2 -49.1(9) . . . . ?
C3 N1 C5 C6 68.1(9) . . . . ?
C4 N2 C2 C1 67.3(8) . . . . ?
C4 N2 C6 C5 -50.3(8) . . . . ?
C4 N2 C7 C8 68.3(9) . . . . ?
C5 N1 C1 C2 66.8(8) . . . . ?
C5 N1 C3 C4 -49.7(9) . . . . ?
C6 N2 C2 C1 -50.3(8) . . . . ?
C6 N2 C4 C3 67.1(8) . . . . ?
C6 N2 C7 C8 -173.1(7) . . . . ?
C7 N2 C2 C1 -169.4(6) . . . . ?
C7 N2 C4 C3 -174.3(7) . . . . ?
C7 N2 C6 C5 -170.8(7) . . . . ?
C7 C8 C9 C9 -179.7(9) . . . 5_655 ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1023707'
#######################################################################
#
#                 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_2-2I2_2PF6
_audit_creation_date             2014-08-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H40 I4 N4, 2(F6 P)'
_chemical_formula_sum            'C20 H40 F12 I4 N4 P2'
_chemical_formula_weight         1134.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H40 N4 F12 P2 I4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1603(6)
_cell_length_b                   9.2796(8)
_cell_length_c                   11.8828(5)
_cell_angle_alpha                96.851(5)
_cell_angle_beta                 90.584(5)
_cell_angle_gamma                111.270(7)
_cell_volume                     831.15(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2736
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      75.8610
_cell_measurement_theta_min      5.1490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    31.229
_exptl_absorpt_correction_T_max  0.264
_exptl_absorpt_correction_T_min  0.080
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             538
_exptl_crystal_size_max          0.2031
_exptl_crystal_size_mid          0.1225
_exptl_crystal_size_min          0.0821
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5124
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.979
_diffrn_reflns_theta_min         3.753
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -107.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
  2 omega  -64.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega  -75.00  -44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  178.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega    2.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       43.8187  -99.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
  5 omega  107.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000 -120.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
  7 omega   73.00  149.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  178.0000 -150.0000 76

#__ type_ start__ end____ width___ exp.time_
  8 omega   65.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
  9 omega   49.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 11 omega   90.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000  -60.0000 85

#__ type_ start__ end____ width___ exp.time_
 12 omega   45.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
 13 omega   48.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000 -150.0000 72

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
 15 omega   89.00  172.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000 -180.0000 83
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1131105000
_diffrn_orient_matrix_UB_12      0.1396148000
_diffrn_orient_matrix_UB_13      0.0860605000
_diffrn_orient_matrix_UB_21      -0.1684410000
_diffrn_orient_matrix_UB_22      0.0167250000
_diffrn_orient_matrix_UB_23      0.0468665000
_diffrn_orient_matrix_UB_31      -0.0035354000
_diffrn_orient_matrix_UB_32      -0.1119305000
_diffrn_orient_matrix_UB_33      0.0866316000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2602
_reflns_number_total             3050
_reflns_odcompleteness_completeness 98.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.566
_refine_diff_density_min         -2.420
_refine_diff_density_rms         0.231
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1167
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.19019(5) 0.24491(5) 0.00401(3) 0.01972(15) Uani 1 1 d . . . . .
I2 I -0.47023(6) 0.23038(5) -0.13748(3) 0.02287(15) Uani 1 1 d . . . . .
N1 N 0.0560(7) 0.2593(6) 0.1377(4) 0.0153(11) Uani 1 1 d . . . . .
N2 N 0.3010(7) 0.2674(7) 0.2756(4) 0.0167(11) Uani 1 1 d . . . . .
C1 C 0.2249(9) 0.3012(9) 0.0809(6) 0.0223(15) Uani 1 1 d . . . . .
H1A H 0.2628 0.4106 0.0649 0.027 Uiso 1 1 calc R . . . .
H1B H 0.2086 0.2330 0.0077 0.027 Uiso 1 1 calc R . . . .
C2 C 0.3674(9) 0.2825(8) 0.1570(5) 0.0180(13) Uani 1 1 d . . . . .
H2A H 0.3912 0.1883 0.1267 0.022 Uiso 1 1 calc R . . . .
H2B H 0.4781 0.3744 0.1591 0.022 Uiso 1 1 calc R . . . .
C3 C 0.0744(10) 0.3775(9) 0.2359(6) 0.0226(14) Uani 1 1 d . . . . .
H3A H -0.0325 0.3447 0.2798 0.027 Uiso 1 1 calc R . . . .
H3B H 0.0873 0.4782 0.2096 0.027 Uiso 1 1 calc R . . . .
C4 C 0.2375(9) 0.3979(8) 0.3124(6) 0.0197(14) Uani 1 1 d . . . . .
H4A H 0.3320 0.4996 0.3060 0.024 Uiso 1 1 calc R . . . .
H4B H 0.2064 0.3961 0.3927 0.024 Uiso 1 1 calc R . . . .
C5 C 0.0141(10) 0.1058(9) 0.1776(6) 0.0227(14) Uani 1 1 d . . . . .
H5A H 0.0160 0.0281 0.1133 0.027 Uiso 1 1 calc R . . . .
H5B H -0.1059 0.0712 0.2060 0.027 Uiso 1 1 calc R . . . .
C6 C 0.1465(9) 0.1144(8) 0.2720(6) 0.0219(14) Uani 1 1 d . . . . .
H6A H 0.0907 0.1086 0.3458 0.026 Uiso 1 1 calc R . . . .
H6B H 0.1872 0.0259 0.2572 0.026 Uiso 1 1 calc R . . . .
C7 C 0.4454(9) 0.2745(9) 0.3615(6) 0.0222(14) Uani 1 1 d . . . . .
H7A H 0.5285 0.3839 0.3784 0.027 Uiso 1 1 calc R . . . .
H7B H 0.3908 0.2425 0.4330 0.027 Uiso 1 1 calc R . . . .
C8 C 0.5485(10) 0.1722(9) 0.3221(6) 0.0228(15) Uani 1 1 d . . . . .
H8A H 0.6225 0.2162 0.2599 0.027 Uiso 1 1 calc R . . . .
H8B H 0.4653 0.0664 0.2919 0.027 Uiso 1 1 calc R . . . .
C9 C 0.6659(10) 0.1604(10) 0.4191(6) 0.0281(16) Uani 1 1 d . . . . .
H9A H 0.7473 0.2669 0.4491 0.034 Uiso 1 1 calc R . . . .
H9B H 0.7384 0.1013 0.3878 0.034 Uiso 1 1 calc R . . . .
C10 C 0.5672(9) 0.0818(9) 0.5183(6) 0.0244(16) Uani 1 1 d . . . . .
H10A H 0.6539 0.0761 0.5748 0.029 Uiso 1 1 calc R . . . .
H10B H 0.5059 0.1474 0.5559 0.029 Uiso 1 1 calc R . . . .
P1 P 0.8643(2) 0.6915(2) 0.33846(14) 0.0195(4) Uani 1 1 d . . . . .
F1 F 0.8793(7) 0.5626(6) 0.4126(4) 0.0387(12) Uani 1 1 d . . . . .
F2 F 0.6662(6) 0.6575(6) 0.3751(4) 0.0381(12) Uani 1 1 d . . . . .
F3 F 0.7908(6) 0.5592(5) 0.2328(4) 0.0325(10) Uani 1 1 d . . . . .
F4 F 0.8485(6) 0.8183(6) 0.2640(4) 0.0385(11) Uani 1 1 d . . . . .
F5 F 1.0607(6) 0.7262(5) 0.3010(4) 0.0317(10) Uani 1 1 d . . . . .
F6 F 0.9356(7) 0.8227(6) 0.4457(4) 0.0407(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.7769(6) . ?
I1 N1 2.503(6) . ?
N1 C1 1.483(8) . ?
N1 C3 1.470(9) . ?
N1 C5 1.477(9) . ?
N2 C2 1.518(7) . ?
N2 C4 1.503(9) . ?
N2 C6 1.515(8) . ?
N2 C7 1.529(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.537(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.544(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.525(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.520(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.530(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.539(9) . ?
C10 C10 1.524(15) 2_656 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
P1 F1 1.605(5) . ?
P1 F2 1.606(4) . ?
P1 F3 1.590(4) . ?
P1 F4 1.593(5) . ?
P1 F5 1.595(4) . ?
P1 F6 1.595(5) . ?

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
N1 I1 I2 177.91(11) . . ?
C1 N1 I1 111.0(4) . . ?
C3 N1 I1 109.8(4) . . ?
C3 N1 C1 108.9(5) . . ?
C3 N1 C5 109.0(5) . . ?
C5 N1 I1 108.7(4) . . ?
C5 N1 C1 109.5(5) . . ?
C2 N2 C7 111.7(5) . . ?
C4 N2 C2 109.2(5) . . ?
C4 N2 C6 108.2(5) . . ?
C4 N2 C7 108.8(5) . . ?
C6 N2 C2 108.6(5) . . ?
C6 N2 C7 110.2(5) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
N1 C1 C2 110.2(5) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
N2 C2 C1 108.2(5) . . ?
N2 C2 H2A 110.1 . . ?
N2 C2 H2B 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
N1 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
N1 C3 C4 109.7(6) . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
N2 C4 C3 109.0(5) . . ?
N2 C4 H4A 109.9 . . ?
N2 C4 H4B 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 C6 110.9(6) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
N2 C6 C5 108.3(5) . . ?
N2 C6 H6A 110.0 . . ?
N2 C6 H6B 110.0 . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
N2 C7 H7A 108.7 . . ?
N2 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 N2 114.2(6) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C7 C8 C9 111.5(6) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C8 C9 C10 115.2(6) . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C10 C10 C9 113.3(7) 2_656 . ?
C10 C10 H10A 108.9 2_656 . ?
C10 C10 H10B 108.9 2_656 . ?
H10A C10 H10B 107.7 . . ?
F1 P1 F2 90.3(3) . . ?
F3 P1 F1 89.1(3) . . ?
F3 P1 F2 89.5(3) . . ?
F3 P1 F4 90.4(3) . . ?
F3 P1 F5 90.3(2) . . ?
F3 P1 F6 179.1(3) . . ?
F4 P1 F1 179.5(3) . . ?
F4 P1 F2 89.6(3) . . ?
F4 P1 F5 89.8(3) . . ?
F4 P1 F6 90.1(3) . . ?
F5 P1 F1 90.3(3) . . ?
F5 P1 F2 179.4(3) . . ?
F6 P1 F1 90.4(3) . . ?
F6 P1 F2 89.7(3) . . ?
F6 P1 F5 90.5(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
I1 N1 C1 C2 -170.4(4) . . . . ?
I1 N1 C3 C4 -174.5(4) . . . . ?
I1 N1 C5 C6 -171.8(4) . . . . ?
N1 C1 C2 N2 -14.2(8) . . . . ?
N1 C3 C4 N2 -12.1(7) . . . . ?
N1 C5 C6 N2 -12.8(8) . . . . ?
N2 C7 C8 C9 -169.3(6) . . . . ?
C1 N1 C3 C4 -52.8(7) . . . . ?
C1 N1 C5 C6 66.8(7) . . . . ?
C2 N2 C4 C3 65.8(6) . . . . ?
C2 N2 C6 C5 -51.9(7) . . . . ?
C2 N2 C7 C8 -46.8(8) . . . . ?
C3 N1 C1 C2 68.7(7) . . . . ?
C3 N1 C5 C6 -52.2(7) . . . . ?
C4 N2 C2 C1 -50.4(7) . . . . ?
C4 N2 C6 C5 66.6(6) . . . . ?
C4 N2 C7 C8 -167.4(6) . . . . ?
C5 N1 C1 C2 -50.4(7) . . . . ?
C5 N1 C3 C4 66.6(7) . . . . ?
C6 N2 C2 C1 67.4(7) . . . . ?
C6 N2 C4 C3 -52.3(6) . . . . ?
C6 N2 C7 C8 74.1(7) . . . . ?
C7 N2 C2 C1 -170.9(6) . . . . ?
C7 N2 C4 C3 -172.0(5) . . . . ?
C7 N2 C6 C5 -174.6(5) . . . . ?
C7 C8 C9 C10 63.5(9) . . . . ?
C8 C9 C10 C10 56.3(11) . . . 2_656 ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2 -6 -1 0.0408 1.9870 -6.0029 -0.9979 -0.6992 -0.4819 0.5784
0 -1 -7 0.0279 -0.0053 -1.0031 -6.9956 -0.7427 -0.3437 -0.4937
-2 6 -2 0.0725 -1.9883 6.0017 -2.0005 0.4409 0.3415 -0.8381
1 -4 7 0.0746 0.9947 -3.9988 6.9977 0.1565 0.0935 1.0503
0 1 7 0.0543 0.0053 1.0031 6.9956 0.7427 0.3437 0.4937
3 4 -2 0.0473 3.0082 3.9992 -2.0049 0.7261 -0.5338 -0.6320
-2 4 -6 0.0592 -1.9944 3.9996 -5.9971 -0.1833 0.1218 -0.9602
-4 2 -5 0.0564 -3.9986 2.0002 -4.9941 -0.6028 0.4729 -0.6424
3 0 -6 0.0259 2.9978 -0.0036 -6.0002 -0.1778 -0.7862 -0.5300
-3 0 6 0.0636 -2.9978 0.0036 6.0002 0.1778 0.7862 0.5300
-5 0 -2 0.0326 -5.0017 0.0012 -1.9932 -0.7371 0.7491 -0.1551

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1023708'
#######################################################################
#
#                 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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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data_2-I6_2-
_audit_creation_date             2014-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H40 N4, 2(I3)'
_chemical_formula_sum            'C20 H40 I6 N4'
_chemical_formula_weight         1097.96
_chemical_melting_point          ?
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.8096(2)
_cell_length_b                   15.32770(10)
_cell_length_c                   22.8613(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5890.27(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    123
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.344
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0933 before and 0.0797 after correction.
The Ratio of minimum to maximum transmission is 0.7790.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             4048
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            37444
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.155
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5012
_reflns_number_total             5750
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.780
_refine_diff_density_min         -4.129
_refine_diff_density_rms         0.296
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5750
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0762P)²+186.3230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1649
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C2(H2a,H2b), C3(H3a,H3b), C4(H4a,H4b), C5(H5a,H5b), C6(H6a,H6b),
 C7(H7a,H7b), C8(H8a,H8b), C9(H9a,H9b), C10(H10a,H10b), C11(H11a,H11b),
 C12(H12a,H12b), C13(H13a,H13b), C14(H14a,H14b), C15(H15a,H15b), C16(H16a,H16b),
  C17(H17a,H17b), C18(H18a,H18b), C19(H19a,H19b), C20(H20a,H20b)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3291(5) -0.3192(5) -0.2077(4) 0.0165(17) Uani 1 1 d . . . . .
N2 N 0.3734(5) -0.2058(5) -0.1319(3) 0.0103(15) Uani 1 1 d . . . . .
N3 N 0.3066(5) 0.4336(5) 0.1249(3) 0.0121(16) Uani 1 1 d . . . . .
N4 N 0.3183(5) 0.5478(5) 0.2058(4) 0.0171(17) Uani 1 1 d . . . . .
C1 C 0.3292(6) -0.2317(6) -0.2341(4) 0.017(2) Uani 1 1 d . . . . .
H1A H 0.2747 -0.2170 -0.2472 0.021 Uiso 1 1 calc R . . . .
H1B H 0.3643 -0.2318 -0.2689 0.021 Uiso 1 1 calc R . . . .
C2 C 0.3584(7) -0.1614(7) -0.1904(4) 0.021(2) Uani 1 1 d . . . . .
H2A H 0.4081 -0.1342 -0.2050 0.026 Uiso 1 1 calc R . . . .
H2B H 0.3177 -0.1152 -0.1860 0.026 Uiso 1 1 calc R . . . .
C3 C 0.2753(6) -0.3193(7) -0.1580(4) 0.020(2) Uani 1 1 d . . . . .
H3A H 0.2758 -0.3778 -0.1397 0.023 Uiso 1 1 calc R . . . .
H3B H 0.2206 -0.3076 -0.1719 0.023 Uiso 1 1 calc R . . . .
C4 C 0.2986(6) -0.2498(7) -0.1114(4) 0.017(2) Uani 1 1 d . . . . .
H4A H 0.2554 -0.2064 -0.1070 0.021 Uiso 1 1 calc R . . . .
H4B H 0.3076 -0.2781 -0.0730 0.021 Uiso 1 1 calc R . . . .
C5 C 0.4101(7) -0.3399(7) -0.1877(5) 0.024(2) Uani 1 1 d . . . . .
H5A H 0.4473 -0.3368 -0.2213 0.028 Uiso 1 1 calc R . . . .
H5B H 0.4114 -0.4002 -0.1722 0.028 Uiso 1 1 calc R . . . .
C6 C 0.4373(6) -0.2752(7) -0.1395(4) 0.018(2) Uani 1 1 d . . . . .
H6A H 0.4455 -0.3067 -0.1022 0.022 Uiso 1 1 calc R . . . .
H6B H 0.4883 -0.2475 -0.1508 0.022 Uiso 1 1 calc R . . . .
C7 C 0.4046(6) -0.1403(6) -0.0868(4) 0.0148(19) Uani 1 1 d . . . . .
H7A H 0.4080 -0.1697 -0.0484 0.018 Uiso 1 1 calc R . . . .
H7B H 0.4592 -0.1229 -0.0982 0.018 Uiso 1 1 calc R . . . .
C8 C 0.3544(6) -0.0584(6) -0.0801(5) 0.018(2) Uani 1 1 d . . . . .
H8A H 0.2992 -0.0746 -0.0696 0.021 Uiso 1 1 calc R . . . .
H8B H 0.3529 -0.0263 -0.1177 0.021 Uiso 1 1 calc R . . . .
C9 C 0.3898(6) 0.0001(6) -0.0323(4) 0.016(2) Uani 1 1 d . . . . .
H9A H 0.3847 -0.0296 0.0060 0.019 Uiso 1 1 calc R . . . .
H9B H 0.4471 0.0089 -0.0402 0.019 Uiso 1 1 calc R . . . .
C10 C 0.3486(6) 0.0886(6) -0.0293(4) 0.017(2) Uani 1 1 d . . . . .
H10A H 0.2907 0.0792 -0.0246 0.021 Uiso 1 1 calc R . . . .
H10B H 0.3570 0.1195 -0.0668 0.021 Uiso 1 1 calc R . . . .
C11 C 0.3779(6) 0.1467(6) 0.0205(4) 0.0148(19) Uani 1 1 d . . . . .
H11A H 0.4341 0.1629 0.0135 0.018 Uiso 1 1 calc R . . . .
H11B H 0.3753 0.1140 0.0578 0.018 Uiso 1 1 calc R . . . .
C12 C 0.3266(6) 0.2304(6) 0.0253(4) 0.016(2) Uani 1 1 d . . . . .
H12A H 0.3304 0.2631 -0.0120 0.019 Uiso 1 1 calc R . . . .
H12B H 0.2703 0.2135 0.0308 0.019 Uiso 1 1 calc R . . . .
C13 C 0.3512(6) 0.2898(6) 0.0749(4) 0.0145(19) Uani 1 1 d . . . . .
H13A H 0.4070 0.3088 0.0694 0.017 Uiso 1 1 calc R . . . .
H13B H 0.3474 0.2583 0.1126 0.017 Uiso 1 1 calc R . . . .
C14 C 0.2966(6) 0.3683(6) 0.0755(4) 0.0144(19) Uani 1 1 d . . . . .
H14A H 0.2411 0.3467 0.0764 0.017 Uiso 1 1 calc R . . . .
H14B H 0.3037 0.3998 0.0380 0.017 Uiso 1 1 calc R . . . .
C15 C 0.3924(6) 0.4573(6) 0.1332(4) 0.0143(19) Uani 1 1 d . . . . .
H15A H 0.4158 0.4766 0.0956 0.017 Uiso 1 1 calc R . . . .
H15B H 0.4228 0.4062 0.1474 0.017 Uiso 1 1 calc R . . . .
C16 C 0.3959(6) 0.5328(7) 0.1790(5) 0.021(2) Uani 1 1 d . . . . .
H16A H 0.4350 0.5179 0.2099 0.025 Uiso 1 1 calc R . . . .
H16B H 0.4140 0.5870 0.1596 0.025 Uiso 1 1 calc R . . . .
C17 C 0.2716(6) 0.3975(6) 0.1807(4) 0.0142(19) Uani 1 1 d . . . . .
H17A H 0.2970 0.3412 0.1908 0.017 Uiso 1 1 calc R . . . .
H17B H 0.2137 0.3878 0.1761 0.017 Uiso 1 1 calc R . . . .
C18 C 0.2877(6) 0.4665(6) 0.2298(4) 0.019(2) Uani 1 1 d . . . . .
H18A H 0.2376 0.4783 0.2512 0.023 Uiso 1 1 calc R . . . .
H18B H 0.3266 0.4425 0.2581 0.023 Uiso 1 1 calc R . . . .
C19 C 0.2615(6) 0.5151(6) 0.1080(4) 0.016(2) Uani 1 1 d . . . . .
H19A H 0.2057 0.5003 0.0984 0.019 Uiso 1 1 calc R . . . .
H19B H 0.2862 0.5423 0.0732 0.019 Uiso 1 1 calc R . . . .
C20 C 0.2640(7) 0.5788(7) 0.1601(5) 0.022(2) Uani 1 1 d . . . . .
H20A H 0.2816 0.6369 0.1463 0.027 Uiso 1 1 calc R . . . .
H20B H 0.2099 0.5851 0.1767 0.027 Uiso 1 1 calc R . . . .
I1 I 0.09468(6) -0.22174(7) -0.25518(5) 0.0515(3) Uani 1 1 d . . . . .
I2 I 0.10789(4) -0.11409(4) -0.15660(3) 0.02083(18) Uani 1 1 d . . . . .
I3 I 0.10954(5) -0.00448(5) -0.05816(4) 0.0322(2) Uani 1 1 d . . . . .
I4 I 0.07785(6) 0.17839(6) 0.03718(4) 0.0378(2) Uani 1 1 d . . . . .
I5 I 0.05509(4) 0.32785(4) 0.10912(3) 0.02107(18) Uani 1 1 d . . . . .
I6 I 0.04085(5) 0.48306(5) 0.17746(3) 0.0319(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.470(12) . ?
N1 C3 1.451(13) . ?
N1 C5 1.472(14) . ?
N2 C2 1.522(12) . ?
N2 C4 1.501(12) . ?
N2 C6 1.523(12) . ?
N2 C7 1.531(12) . ?
N3 C14 1.520(11) . ?
N3 C15 1.499(12) . ?
N3 C17 1.510(11) . ?
N3 C19 1.511(11) . ?
N4 C16 1.458(13) . ?
N4 C18 1.457(13) . ?
N4 C20 1.465(13) . ?
C1 C2 1.549(13) . ?
C3 C4 1.557(13) . ?
C5 C6 1.553(14) . ?
C7 C8 1.520(13) . ?
C8 C9 1.533(13) . ?
C9 C10 1.524(13) . ?
C10 C11 1.526(13) . ?
C11 C12 1.550(13) . ?
C12 C13 1.512(13) . ?
C13 C14 1.513(13) . ?
C15 C16 1.563(13) . ?
C17 C18 1.566(12) . ?
C19 C20 1.541(14) . ?
I1 I2 2.8018(12) . ?
I2 I3 2.8087(11) . ?
I4 I5 2.8461(11) . ?
I5 I6 2.8561(11) . ?

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
C1 N1 C5 108.8(8) . . ?
C3 N1 C1 108.9(8) . . ?
C3 N1 C5 109.5(8) . . ?
C2 N2 C6 109.2(7) . . ?
C2 N2 C7 110.8(7) . . ?
C4 N2 C2 109.7(7) . . ?
C4 N2 C6 108.2(7) . . ?
C4 N2 C7 111.8(7) . . ?
C6 N2 C7 107.0(7) . . ?
C15 N3 C14 111.1(7) . . ?
C15 N3 C17 111.0(7) . . ?
C15 N3 C19 108.3(7) . . ?
C17 N3 C14 110.1(7) . . ?
C17 N3 C19 108.9(7) . . ?
C19 N3 C14 107.4(7) . . ?
C16 N4 C20 108.0(8) . . ?
C18 N4 C16 109.8(8) . . ?
C18 N4 C20 109.0(8) . . ?
N1 C1 C2 111.8(8) . . ?
N2 C2 C1 107.9(8) . . ?
N1 C3 C4 112.2(8) . . ?
N2 C4 C3 107.7(8) . . ?
N1 C5 C6 110.8(8) . . ?
N2 C6 C5 108.6(8) . . ?
C8 C7 N2 114.8(8) . . ?
C7 C8 C9 109.8(8) . . ?
C10 C9 C8 112.1(8) . . ?
C9 C10 C11 114.0(8) . . ?
C10 C11 C12 110.8(8) . . ?
C13 C12 C11 113.5(8) . . ?
C12 C13 C14 108.6(8) . . ?
C13 C14 N3 117.6(8) . . ?
N3 C15 C16 107.4(8) . . ?
N4 C16 C15 111.4(8) . . ?
N3 C17 C18 106.9(7) . . ?
N4 C18 C17 111.6(8) . . ?
N3 C19 C20 108.2(8) . . ?
N4 C20 C19 111.2(8) . . ?
I1 I2 I3 175.98(4) . . ?
I4 I5 I6 176.24(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
N1 C1 C2 N2 -3.3(12) . . . . ?
N1 C3 C4 N2 -2.4(11) . . . . ?
N1 C5 C6 N2 -4.7(11) . . . . ?
N2 C7 C8 C9 177.8(8) . . . . ?
N3 C15 C16 N4 8.5(11) . . . . ?
N3 C17 C18 N4 9.4(11) . . . . ?
N3 C19 C20 N4 8.6(12) . . . . ?
C1 N1 C3 C4 -57.8(10) . . . . ?
C1 N1 C5 C6 62.7(10) . . . . ?
C2 N2 C4 C3 60.6(10) . . . . ?
C2 N2 C6 C5 -56.6(10) . . . . ?
C2 N2 C7 C8 52.2(11) . . . . ?
C3 N1 C1 C2 61.0(11) . . . . ?
C3 N1 C5 C6 -56.2(10) . . . . ?
C4 N2 C2 C1 -57.5(10) . . . . ?
C4 N2 C6 C5 62.8(10) . . . . ?
C4 N2 C7 C8 -70.5(10) . . . . ?
C5 N1 C1 C2 -58.3(11) . . . . ?
C5 N1 C3 C4 61.0(10) . . . . ?
C6 N2 C2 C1 60.9(10) . . . . ?
C6 N2 C4 C3 -58.4(9) . . . . ?
C6 N2 C7 C8 171.1(8) . . . . ?
C7 N2 C2 C1 178.5(8) . . . . ?
C7 N2 C4 C3 -176.0(7) . . . . ?
C7 N2 C6 C5 -176.6(8) . . . . ?
C7 C8 C9 C10 172.3(8) . . . . ?
C8 C9 C10 C11 175.9(8) . . . . ?
C9 C10 C11 C12 -173.3(8) . . . . ?
C10 C11 C12 C13 178.5(8) . . . . ?
C11 C12 C13 C14 -179.4(8) . . . . ?
C12 C13 C14 N3 175.5(8) . . . . ?
C14 N3 C15 C16 173.0(7) . . . . ?
C14 N3 C17 C18 177.5(8) . . . . ?
C14 N3 C19 C20 174.6(8) . . . . ?
C15 N3 C14 C13 47.7(11) . . . . ?
C15 N3 C17 C18 54.1(10) . . . . ?
C15 N3 C19 C20 -65.4(10) . . . . ?
C16 N4 C18 C17 -64.4(11) . . . . ?
C16 N4 C20 C19 54.8(11) . . . . ?
C17 N3 C14 C13 -75.6(10) . . . . ?
C17 N3 C15 C16 -64.2(9) . . . . ?
C17 N3 C19 C20 55.4(10) . . . . ?
C18 N4 C16 C15 53.8(11) . . . . ?
C18 N4 C20 C19 -64.6(11) . . . . ?
C19 N3 C14 C13 166.0(8) . . . . ?
C19 N3 C15 C16 55.3(9) . . . . ?
C19 N3 C17 C18 -65.0(10) . . . . ?
C20 N4 C16 C15 -65.0(10) . . . . ?
C20 N4 C18 C17 53.8(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1023709'
#######################################################################
#
#                 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_2-I12_2-
_audit_creation_date             2014-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H40 I4 N4, 2.67(I3)'
_chemical_formula_sum            'C20 H40 I12 N4'
_chemical_formula_weight         1859.36
_chemical_melting_point          ?
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8468(5)
_cell_length_b                   9.2378(4)
_cell_length_c                   13.5621(8)
_cell_angle_alpha                102.188(3)
_cell_angle_beta                 92.217(2)
_cell_angle_gamma                106.349(3)
_cell_volume                     1033.87(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    123
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.004
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0748 after correction.
The Ratio of minimum to maximum transmission is 0.7409.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'metallic blackish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.986
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13721
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.362
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3129
_reflns_number_total             3625
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.224
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+10.7581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0780
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.26109(6) 1.15412(6) 0.43704(4) 0.02078(15) Uani 1 1 d . . . . .
I2 I 1.26950(6) 1.44483(6) 0.55229(5) 0.02209(15) Uani 1 1 d . . . . .
I3 I 0.79259(7) 1.19405(6) 0.33318(5) 0.02840(16) Uani 1 1 d . . . . .
I4 I 0.75544(6) 0.88399(6) 0.22313(4) 0.02064(15) Uani 1 1 d . . . . .
I5 I 0.71583(7) 0.55302(6) 0.11689(5) 0.02950(17) Uani 1 1 d . . . . .
I6 I 0.55654(7) 0.15658(7) 0.04097(5) 0.02891(16) Uani 1 1 d . . . . .
N1 N 1.2517(8) 0.8835(8) 0.3440(6) 0.0190(16) Uani 1 1 d . . . . .
N2 N 1.2379(7) 0.6052(7) 0.2631(5) 0.0168(15) Uani 1 1 d . . . . .
C1 C 1.3855(9) 0.8459(9) 0.3886(6) 0.0159(18) Uani 1 1 d . . . . .
H1A H 1.3774 0.8527 0.4619 0.019 Uiso 1 1 calc R . . . .
H1B H 1.4861 0.9218 0.3809 0.019 Uiso 1 1 calc R . . . .
C2 C 1.3859(9) 0.6818(9) 0.3360(7) 0.0190(19) Uani 1 1 d . . . . .
H2A H 1.4806 0.6870 0.2988 0.023 Uiso 1 1 calc R . . . .
H2B H 1.3894 0.6204 0.3872 0.023 Uiso 1 1 calc R . . . .
C3 C 1.1018(9) 0.7775(9) 0.3631(7) 0.0193(19) Uani 1 1 d . . . . .
H3A H 1.0111 0.7998 0.3311 0.023 Uiso 1 1 calc R . . . .
H3B H 1.0937 0.7947 0.4371 0.023 Uiso 1 1 calc R . . . .
C4 C 1.0954(9) 0.6076(9) 0.3199(7) 0.0207(19) Uani 1 1 d . . . . .
H4A H 1.0954 0.5537 0.3757 0.025 Uiso 1 1 calc R . . . .
H4B H 0.9971 0.5534 0.2736 0.025 Uiso 1 1 calc R . . . .
C5 C 1.2617(11) 0.8655(9) 0.2339(7) 0.025(2) Uani 1 1 d . . . . .
H5A H 1.3659 0.9309 0.2220 0.030 Uiso 1 1 calc R . . . .
H5B H 1.1782 0.9004 0.2040 0.030 Uiso 1 1 calc R . . . .
C6 C 1.2410(11) 0.6959(9) 0.1828(7) 0.024(2) Uani 1 1 d . . . . .
H6A H 1.1409 0.6526 0.1373 0.029 Uiso 1 1 calc R . . . .
H6B H 1.3296 0.6885 0.1416 0.029 Uiso 1 1 calc R . . . .
C7 C 1.2353(9) 0.4375(9) 0.2173(7) 0.022(2) Uani 1 1 d . . . . .
H7A H 1.3358 0.4398 0.1871 0.026 Uiso 1 1 calc R . . . .
H7B H 1.2318 0.3827 0.2729 0.026 Uiso 1 1 calc R . . . .
C8 C 1.1014(10) 0.3459(9) 0.1384(7) 0.022(2) Uani 1 1 d . . . . .
H8A H 1.1070 0.3940 0.0794 0.026 Uiso 1 1 calc R . . . .
H8B H 0.9992 0.3439 0.1662 0.026 Uiso 1 1 calc R . . . .
C9 C 1.1129(10) 0.1808(10) 0.1055(7) 0.026(2) Uani 1 1 d . . . . .
H9A H 1.2207 0.1856 0.0861 0.032 Uiso 1 1 calc R . . . .
H9B H 1.0973 0.1312 0.1638 0.032 Uiso 1 1 calc R . . . .
C10 C 0.9918(9) 0.0806(9) 0.0166(7) 0.0198(19) Uani 1 1 d . . . . .
H10A H 0.8838 0.0728 0.0366 0.024 Uiso 1 1 calc R . . . .
H10B H 1.0053 0.1313 -0.0412 0.024 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 I2 2.7869(7) . ?
I1 N1 2.528(7) . ?
I3 I4 2.8577(8) . ?
I4 I5 3.0074(8) . ?
I6 I6 2.7444(12) 2_655 ?
N1 C1 1.467(10) . ?
N1 C3 1.479(10) . ?
N1 C5 1.476(11) . ?
N2 C2 1.508(10) . ?
N2 C4 1.505(10) . ?
N2 C6 1.504(11) . ?
N2 C7 1.536(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.535(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.539(11) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.529(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.489(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.530(11) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.526(12) . ?
C10 C10 1.512(15) 2_755 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
N1 I1 I2 175.91(16) . . ?
I3 I4 I5 177.24(3) . . ?
C1 N1 I1 107.5(5) . . ?
C1 N1 C3 109.2(6) . . ?
C1 N1 C5 108.8(6) . . ?
C3 N1 I1 106.9(5) . . ?
C5 N1 I1 114.0(5) . . ?
C5 N1 C3 110.3(7) . . ?
C2 N2 C7 108.0(6) . . ?
C4 N2 C2 109.1(6) . . ?
C4 N2 C7 110.5(6) . . ?
C6 N2 C2 108.5(6) . . ?
C6 N2 C4 109.1(6) . . ?
C6 N2 C7 111.6(6) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
N1 C1 C2 110.2(6) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
N2 C2 C1 109.1(6) . . ?
N2 C2 H2A 109.9 . . ?
N2 C2 H2B 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N1 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
N1 C3 C4 110.4(6) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
N2 C4 C3 108.6(6) . . ?
N2 C4 H4A 110.0 . . ?
N2 C4 H4B 110.0 . . ?
C3 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
N1 C5 C6 110.3(7) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
N2 C6 C5 109.1(7) . . ?
N2 C6 H6A 109.9 . . ?
N2 C6 H6B 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 H7A 108.4 . . ?
N2 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 N2 115.7(6) . . ?
C8 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
C7 C8 C9 108.5(7) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 C8 113.2(7) . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C10 C10 C9 112.3(9) 2_755 . ?
C10 C10 H10A 109.1 2_755 . ?
C10 C10 H10B 109.1 2_755 . ?
H10A C10 H10B 107.9 . . ?

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
I1 N1 C1 C2 179.5(5) . . . . ?
I1 N1 C3 C4 -173.2(6) . . . . ?
I1 N1 C5 C6 -175.2(5) . . . . ?
N1 C1 C2 N2 -6.2(9) . . . . ?
N1 C3 C4 N2 -5.3(9) . . . . ?
N1 C5 C6 N2 -7.2(9) . . . . ?
N2 C7 C8 C9 -177.2(7) . . . . ?
C1 N1 C3 C4 -57.1(9) . . . . ?
C1 N1 C5 C6 64.8(8) . . . . ?
C2 N2 C4 C3 62.1(8) . . . . ?
C2 N2 C6 C5 -55.0(8) . . . . ?
C2 N2 C7 C8 -176.6(7) . . . . ?
C3 N1 C1 C2 63.8(9) . . . . ?
C3 N1 C5 C6 -54.9(9) . . . . ?
C4 N2 C2 C1 -55.9(8) . . . . ?
C4 N2 C6 C5 63.7(8) . . . . ?
C4 N2 C7 C8 64.2(9) . . . . ?
C5 N1 C1 C2 -56.6(8) . . . . ?
C5 N1 C3 C4 62.3(8) . . . . ?
C6 N2 C2 C1 62.9(8) . . . . ?
C6 N2 C4 C3 -56.2(8) . . . . ?
C6 N2 C7 C8 -57.4(9) . . . . ?
C7 N2 C2 C1 -176.0(7) . . . . ?
C7 N2 C4 C3 -179.3(7) . . . . ?
C7 N2 C6 C5 -173.9(6) . . . . ?
C7 C8 C9 C10 -173.9(8) . . . . ?
C8 C9 C10 C10 178.4(9) . . . 2_755 ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1023710'
