# Electronic Supplementary Material (ESI) for ChemComm.
# 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
#  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_mo_40106a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 I N2'
_chemical_formula_weight         404.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.668(3)
_cell_length_b                   10.397(3)
_cell_length_c                   10.757(3)
_cell_angle_alpha                108.642(4)
_cell_angle_beta                 99.276(4)
_cell_angle_gamma                101.841(5)
_cell_volume                     871.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4410
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.83

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.836
_shelx_estimated_absorpt_T_min   0.667
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.524
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6305
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.061
_diffrn_reflns_theta_max         27.934
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4081
_reflns_number_gt                3685
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0848P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4081
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_restrained_S_all      1.215
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.30195(3) 0.33193(3) 0.08990(2) 0.03329(13) Uani 1 1 d . . . . .
N1 N 0.8081(4) 0.4411(3) 0.2188(3) 0.0233(6) Uani 1 1 d . . . . .
N2 N 0.7239(4) 0.3094(3) 0.0041(3) 0.0277(6) Uani 1 1 d . . . . .
C1 C 0.7186(4) 0.4227(4) 0.1005(3) 0.0214(6) Uani 1 1 d . . . . .
C2 C 0.8753(6) 0.3188(4) 0.2099(4) 0.0325(8) Uani 1 1 d . . . . .
H2A H 0.8220 0.2608 0.2564 0.039 Uiso 1 1 calc R U . . .
H2B H 0.9941 0.3503 0.2497 0.039 Uiso 1 1 calc R U . . .
C3 C 0.8357(5) 0.2373(4) 0.0575(4) 0.0304(8) Uani 1 1 d . . . . .
H3 H 0.9369 0.2520 0.0245 0.036 Uiso 1 1 calc R U . . .
C4 C 0.7404(6) 0.0827(4) -0.0067(4) 0.0354(9) Uani 1 1 d . . . . .
H4A H 0.8128 0.0213 -0.0310 0.043 Uiso 1 1 calc R U . . .
H4B H 0.6787 0.0535 0.0541 0.043 Uiso 1 1 calc R U . . .
C5 C 0.6274(5) 0.0793(4) -0.1318(4) 0.0289(7) Uani 1 1 d . . . . .
C6 C 0.5381(6) -0.0334(5) -0.2485(5) 0.0444(10) Uani 1 1 d . . . . .
H6 H 0.5452 -0.1264 -0.2604 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4392(6) -0.0089(5) -0.3469(5) 0.0465(11) Uani 1 1 d . . . . .
H7 H 0.3769 -0.0860 -0.4265 0.056 Uiso 1 1 calc R U . . .
C8 C 0.4288(5) 0.1257(5) -0.3321(4) 0.0412(10) Uani 1 1 d . . . . .
H8 H 0.3602 0.1400 -0.4018 0.049 Uiso 1 1 calc R U . . .
C9 C 0.5182(5) 0.2412(5) -0.2154(4) 0.0352(9) Uani 1 1 d . . . . .
H9 H 0.5123 0.3345 -0.2035 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6155(4) 0.2122(4) -0.1185(3) 0.0250(7) Uani 1 1 d . . . . .
C11 C 0.8453(4) 0.5637(4) 0.3394(3) 0.0219(6) Uani 1 1 d . . . . .
C12 C 0.9606(4) 0.6840(4) 0.3513(3) 0.0234(6) Uani 1 1 d . . . . .
C13 C 0.9944(4) 0.8034(4) 0.4690(3) 0.0254(7) Uani 1 1 d . . . . .
H13 H 1.0720 0.8873 0.4787 0.031 Uiso 1 1 calc R U . . .
C14 C 0.9168(5) 0.8019(4) 0.5722(3) 0.0253(7) Uani 1 1 d . . . . .
C15 C 0.8058(5) 0.6795(4) 0.5584(3) 0.0266(7) Uani 1 1 d . . . . .
H15 H 0.7527 0.6784 0.6289 0.032 Uiso 1 1 calc R U . . .
C16 C 0.7695(4) 0.5579(4) 0.4444(3) 0.0235(6) Uani 1 1 d . . . . .
C17 C 1.0476(6) 0.6873(5) 0.2413(4) 0.0349(8) Uani 1 1 d . . . . .
H17A H 1.0748 0.5978 0.2053 0.052 Uiso 1 1 calc R U . . .
H17B H 1.1476 0.7652 0.2787 0.052 Uiso 1 1 calc R U . . .
H17C H 0.9770 0.7009 0.1685 0.052 Uiso 1 1 calc R U . . .
C18 C 0.9585(6) 0.9322(4) 0.7006(4) 0.0370(9) Uani 1 1 d . . . . .
H18A H 0.8860 0.9909 0.6899 0.056 Uiso 1 1 calc R U . . .
H18B H 1.0715 0.9863 0.7174 0.056 Uiso 1 1 calc R U . . .
H18C H 0.9449 0.9032 0.7773 0.056 Uiso 1 1 calc R U . . .
C19 C 0.6557(5) 0.4216(4) 0.4355(4) 0.0347(8) Uani 1 1 d . . . . .
H19A H 0.7151 0.3500 0.4292 0.052 Uiso 1 1 calc R U . . .
H19B H 0.5653 0.3883 0.3551 0.052 Uiso 1 1 calc R U . . .
H19C H 0.6130 0.4384 0.5166 0.052 Uiso 1 1 calc R U . . .
H1 H 0.659(5) 0.483(4) 0.083(4) 0.015(9) Uiso 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 1.312(4) . ?
N1 C11 1.432(4) . ?
N1 C2 1.487(5) . ?
N2 C1 1.312(4) . ?
N2 C10 1.416(4) . ?
N2 C3 1.491(5) . ?
C1 H1 0.94(4) . ?
C2 C3 1.528(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.518(6) . ?
C3 H3 1.0000 . ?
C4 C5 1.516(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.370(6) . ?
C5 C6 1.386(6) . ?
C6 C7 1.374(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(5) . ?
C9 H9 0.9500 . ?
C11 C12 1.388(5) . ?
C11 C16 1.406(5) . ?
C12 C13 1.399(5) . ?
C12 C17 1.507(5) . ?
C13 C14 1.390(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(5) . ?
C14 C18 1.522(5) . ?
C15 C16 1.387(5) . ?
C15 H15 0.9500 . ?
C16 C19 1.517(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 126.0(3) . . ?
C1 N1 C2 110.5(3) . . ?
C11 N1 C2 123.5(3) . . ?
C1 N2 C10 135.3(3) . . ?
C1 N2 C3 110.9(3) . . ?
C10 N2 C3 109.1(3) . . ?
N2 C1 N1 112.6(3) . . ?
N2 C1 H1 122(2) . . ?
N1 C1 H1 126(2) . . ?
N1 C2 C3 102.7(3) . . ?
N1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
N1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
N2 C3 C4 103.1(3) . . ?
N2 C3 C2 102.0(3) . . ?
C4 C3 C2 122.2(4) . . ?
N2 C3 H3 109.5 . . ?
C4 C3 H3 109.5 . . ?
C2 C3 H3 109.5 . . ?
C5 C4 C3 102.0(3) . . ?
C5 C4 H4A 111.4 . . ?
C3 C4 H4A 111.4 . . ?
C5 C4 H4B 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H4A C4 H4B 109.2 . . ?
C10 C5 C6 118.9(4) . . ?
C10 C5 C4 110.6(3) . . ?
C6 C5 C4 130.4(4) . . ?
C7 C6 C5 119.2(4) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 121.2(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 120.7(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 116.3(4) . . ?
C10 C9 H9 121.8 . . ?
C8 C9 H9 121.8 . . ?
C5 C10 C9 123.7(4) . . ?
C5 C10 N2 108.5(3) . . ?
C9 C10 N2 127.8(4) . . ?
C12 C11 C16 121.7(3) . . ?
C12 C11 N1 118.6(3) . . ?
C16 C11 N1 119.7(3) . . ?
C11 C12 C13 118.0(3) . . ?
C11 C12 C17 121.4(3) . . ?
C13 C12 C17 120.6(3) . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 C18 120.6(3) . . ?
C13 C14 C18 120.3(4) . . ?
C14 C15 C16 121.7(3) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C11 118.0(3) . . ?
C15 C16 C19 120.8(3) . . ?
C11 C16 C19 121.1(3) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N2 C1 N1 150.1(4) . . . . ?
C3 N2 C1 N1 -2.0(4) . . . . ?
C11 N1 C1 N2 171.0(3) . . . . ?
C2 N1 C1 N2 -5.8(5) . . . . ?
C1 N1 C2 C3 10.6(4) . . . . ?
C11 N1 C2 C3 -166.3(3) . . . . ?
C1 N2 C3 C4 135.8(4) . . . . ?
C10 N2 C3 C4 -23.8(4) . . . . ?
C1 N2 C3 C2 8.4(4) . . . . ?
C10 N2 C3 C2 -151.2(3) . . . . ?
N1 C2 C3 N2 -10.7(4) . . . . ?
N1 C2 C3 C4 -124.8(4) . . . . ?
N2 C3 C4 C5 24.5(4) . . . . ?
C2 C3 C4 C5 138.0(4) . . . . ?
C3 C4 C5 C10 -18.9(4) . . . . ?
C3 C4 C5 C6 162.5(5) . . . . ?
C10 C5 C6 C7 -0.6(7) . . . . ?
C4 C5 C6 C7 177.9(5) . . . . ?
C5 C6 C7 C8 0.8(8) . . . . ?
C6 C7 C8 C9 -0.5(8) . . . . ?
C7 C8 C9 C10 0.1(7) . . . . ?
C6 C5 C10 C9 0.3(6) . . . . ?
C4 C5 C10 C9 -178.5(4) . . . . ?
C6 C5 C10 N2 -176.6(4) . . . . ?
C4 C5 C10 N2 4.6(5) . . . . ?
C8 C9 C10 C5 0.0(6) . . . . ?
C8 C9 C10 N2 176.3(4) . . . . ?
C1 N2 C10 C5 -140.0(4) . . . . ?
C3 N2 C10 C5 12.4(4) . . . . ?
C1 N2 C10 C9 43.2(7) . . . . ?
C3 N2 C10 C9 -164.3(4) . . . . ?
C1 N1 C11 C12 -76.1(5) . . . . ?
C2 N1 C11 C12 100.3(4) . . . . ?
C1 N1 C11 C16 106.3(4) . . . . ?
C2 N1 C11 C16 -77.3(5) . . . . ?
C16 C11 C12 C13 -3.2(5) . . . . ?
N1 C11 C12 C13 179.3(3) . . . . ?
C16 C11 C12 C17 176.8(3) . . . . ?
N1 C11 C12 C17 -0.7(5) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C17 C12 C13 C14 -179.2(3) . . . . ?
C12 C13 C14 C15 0.8(5) . . . . ?
C12 C13 C14 C18 178.6(3) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C18 C14 C15 C16 -177.8(3) . . . . ?
C14 C15 C16 C11 -2.3(5) . . . . ?
C14 C15 C16 C19 175.8(3) . . . . ?
C12 C11 C16 C15 3.9(5) . . . . ?
N1 C11 C16 C15 -178.6(3) . . . . ?
C12 C11 C16 C19 -174.2(3) . . . . ?
N1 C11 C16 C19 3.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 I1 1.00 3.00 3.888(4) 148.0 1_655

_refine_diff_density_max         1.129
_refine_diff_density_min         -1.223
_refine_diff_density_rms         0.205

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 1017139'
#######################################################################
#
#                 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
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data_mo_40107b

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 I N2'
_chemical_formula_weight         368.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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. 
;

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

_cell_length_a                   11.3435(19)
_cell_length_b                   12.737(2)
_cell_length_c                   24.224(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3499.9(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2515
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      21.61

_exptl_crystal_description       sheet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.821
_shelx_estimated_absorpt_T_min   0.811
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24480
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.460
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4030
_reflns_number_gt                2517
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0441P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4030
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.000 0.500 176.7 21.4
2 0.000 0.500 1.000 176.7 21.4
3 0.500 0.000 0.000 176.7 22.0
4 0.500 0.500 0.500 176.7 22.0
_platon_squeeze_details          
; 
;

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 0.05185(3) 0.51535(2) 0.19861(2) 0.04094(12) Uani 1 1 d . . . . .
N1 N 0.7478(3) 0.2902(3) 0.25556(13) 0.0283(8) Uani 1 1 d . . . . .
N2 N 0.8463(3) 0.3554(3) 0.32548(14) 0.0309(8) Uani 1 1 d . . . . .
C1 C 0.8191(4) 0.3639(3) 0.27239(17) 0.0263(9) Uani 1 1 d . . . . .
C2 C 0.8691(4) 0.4326(3) 0.36620(16) 0.0275(9) Uani 1 1 d . . . . .
C3 C 0.9409(4) 0.5206(3) 0.36154(17) 0.0315(9) Uani 1 1 d . . . . .
H3 H 0.9807 0.5373 0.3282 0.038 Uiso 1 1 calc R U . . .
C4 C 0.9511(4) 0.5828(3) 0.40842(19) 0.0346(10) Uani 1 1 d . . . . .
H4 H 0.9990 0.6439 0.4071 0.041 Uiso 1 1 calc R U . . .
C5 C 0.8929(4) 0.5577(4) 0.45731(19) 0.0405(11) Uani 1 1 d . . . . .
H5 H 0.9022 0.6007 0.4890 0.049 Uiso 1 1 calc R U . . .
C6 C 0.8212(5) 0.4698(4) 0.45944(19) 0.0448(13) Uani 1 1 d . . . . .
H6 H 0.7810 0.4528 0.4927 0.054 Uiso 1 1 calc R U . . .
C7 C 0.8079(4) 0.4065(4) 0.41351(17) 0.0345(11) Uani 1 1 d . . . . .
C8 C 0.7317(5) 0.3126(4) 0.40409(18) 0.0453(13) Uani 1 1 d . . . . .
H8A H 0.6483 0.3331 0.3989 0.054 Uiso 1 1 calc R U . . .
H8B H 0.7373 0.2627 0.4353 0.054 Uiso 1 1 calc R U . . .
C9 C 0.7837(5) 0.2648(3) 0.35069(18) 0.0393(12) Uani 1 1 d . . . . .
H9 H 0.8413 0.2082 0.3601 0.047 Uiso 1 1 calc R U . . .
C10 C 0.7039(4) 0.2288(3) 0.30337(17) 0.0376(11) Uani 1 1 d . . . . .
H10A H 0.7120 0.1524 0.2968 0.045 Uiso 1 1 calc R U . . .
H10B H 0.6202 0.2451 0.3112 0.045 Uiso 1 1 calc R U . . .
C11 C 0.7083(4) 0.2694(3) 0.19964(17) 0.0295(9) Uani 1 1 d . . . . .
H11 H 0.6229 0.2499 0.2013 0.035 Uiso 1 1 calc R U . . .
C12 C 0.7195(5) 0.3652(3) 0.16298(17) 0.0398(12) Uani 1 1 d . . . . .
H12A H 0.8030 0.3877 0.1615 0.048 Uiso 1 1 calc R U . . .
H12B H 0.6726 0.4236 0.1787 0.048 Uiso 1 1 calc R U . . .
C13 C 0.6756(5) 0.3405(4) 0.10425(19) 0.0486(14) Uani 1 1 d . . . . .
H13A H 0.5901 0.3247 0.1054 0.058 Uiso 1 1 calc R U . . .
H13B H 0.6872 0.4027 0.0804 0.058 Uiso 1 1 calc R U . . .
C14 C 0.7406(5) 0.2485(3) 0.08018(17) 0.0422(12) Uani 1 1 d . . . . .
H14A H 0.8246 0.2672 0.0752 0.051 Uiso 1 1 calc R U . . .
H14B H 0.7074 0.2315 0.0435 0.051 Uiso 1 1 calc R U . . .
C15 C 0.7314(5) 0.1534(4) 0.11729(17) 0.0399(12) Uani 1 1 d . . . . .
H15A H 0.7788 0.0954 0.1015 0.048 Uiso 1 1 calc R U . . .
H15B H 0.6483 0.1300 0.1189 0.048 Uiso 1 1 calc R U . . .
C16 C 0.7748(5) 0.1770(3) 0.17552(17) 0.0373(12) Uani 1 1 d . . . . .
H16A H 0.7632 0.1145 0.1992 0.045 Uiso 1 1 calc R U . . .
H16B H 0.8601 0.1932 0.1746 0.045 Uiso 1 1 calc R U . . .
H1 H 0.855(3) 0.419(3) 0.2495(16) 0.025(11) Uiso 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 1.305(5) . ?
N1 C11 1.451(5) . ?
N1 C10 1.483(5) . ?
N2 C1 1.327(5) . ?
N2 C2 1.417(5) . ?
N2 C9 1.486(6) . ?
C1 H1 0.98(4) . ?
C2 C7 1.381(6) . ?
C2 C3 1.390(6) . ?
C3 C4 1.389(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.493(6) . ?
C8 C9 1.546(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.531(6) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.515(6) . ?
C11 C12 1.515(6) . ?
C11 H11 1.0000 . ?
C12 C13 1.540(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.503(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.512(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.524(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 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
C1 N1 C11 127.9(3) . . ?
C1 N1 C10 110.1(3) . . ?
C11 N1 C10 121.9(3) . . ?
C1 N2 C2 131.4(4) . . ?
C1 N2 C9 110.5(4) . . ?
C2 N2 C9 109.9(3) . . ?
N1 C1 N2 112.8(4) . . ?
N1 C1 H1 127(2) . . ?
N2 C1 H1 121(2) . . ?
C7 C2 C3 123.8(4) . . ?
C7 C2 N2 108.6(4) . . ?
C3 C2 N2 127.6(4) . . ?
C4 C3 C2 116.3(4) . . ?
C4 C3 H3 121.9 . . ?
C2 C3 H3 121.9 . . ?
C3 C4 C5 121.6(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 119.7(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C2 C7 C6 118.3(4) . . ?
C2 C7 C8 110.9(4) . . ?
C6 C7 C8 130.8(4) . . ?
C7 C8 C9 102.9(4) . . ?
C7 C8 H8A 111.2 . . ?
C9 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
N2 C9 C10 102.0(3) . . ?
N2 C9 C8 102.7(3) . . ?
C10 C9 C8 121.3(4) . . ?
N2 C9 H9 110.0 . . ?
C10 C9 H9 110.0 . . ?
C8 C9 H9 110.0 . . ?
N1 C10 C9 103.2(3) . . ?
N1 C10 H10A 111.1 . . ?
C9 C10 H10A 111.1 . . ?
N1 C10 H10B 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
N1 C11 C16 110.3(4) . . ?
N1 C11 C12 112.0(3) . . ?
C16 C11 C12 111.0(4) . . ?
N1 C11 H11 107.8 . . ?
C16 C11 H11 107.8 . . ?
C12 C11 H11 107.8 . . ?
C11 C12 C13 110.4(4) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 111.0(4) . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 111.1(4) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 111.7(4) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C11 C16 C15 110.5(4) . . ?
C11 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C11 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?

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
C11 N1 C1 N2 -174.0(4) . . . . ?
C10 N1 C1 N2 8.9(5) . . . . ?
C2 N2 C1 N1 -146.1(4) . . . . ?
C9 N2 C1 N1 -1.6(5) . . . . ?
C1 N2 C2 C7 134.3(5) . . . . ?
C9 N2 C2 C7 -10.4(5) . . . . ?
C1 N2 C2 C3 -46.1(7) . . . . ?
C9 N2 C2 C3 169.2(4) . . . . ?
C7 C2 C3 C4 1.3(6) . . . . ?
N2 C2 C3 C4 -178.2(4) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 -1.1(7) . . . . ?
C4 C5 C6 C7 0.5(8) . . . . ?
C3 C2 C7 C6 -1.9(7) . . . . ?
N2 C2 C7 C6 177.7(4) . . . . ?
C3 C2 C7 C8 175.6(4) . . . . ?
N2 C2 C7 C8 -4.8(5) . . . . ?
C5 C6 C7 C2 1.0(7) . . . . ?
C5 C6 C7 C8 -175.9(5) . . . . ?
C2 C7 C8 C9 17.0(5) . . . . ?
C6 C7 C8 C9 -165.9(5) . . . . ?
C1 N2 C9 C10 -5.9(5) . . . . ?
C2 N2 C9 C10 146.5(4) . . . . ?
C1 N2 C9 C8 -132.2(4) . . . . ?
C2 N2 C9 C8 20.2(5) . . . . ?
C7 C8 C9 N2 -21.5(5) . . . . ?
C7 C8 C9 C10 -134.2(4) . . . . ?
C1 N1 C10 C9 -11.9(5) . . . . ?
C11 N1 C10 C9 170.7(4) . . . . ?
N2 C9 C10 N1 10.1(5) . . . . ?
C8 C9 C10 N1 123.1(4) . . . . ?
C1 N1 C11 C16 102.2(5) . . . . ?
C10 N1 C11 C16 -81.0(5) . . . . ?
C1 N1 C11 C12 -21.9(6) . . . . ?
C10 N1 C11 C12 154.9(4) . . . . ?
N1 C11 C12 C13 -179.4(4) . . . . ?
C16 C11 C12 C13 56.8(5) . . . . ?
C11 C12 C13 C14 -56.3(6) . . . . ?
C12 C13 C14 C15 55.6(6) . . . . ?
C13 C14 C15 C16 -55.7(6) . . . . ?
N1 C11 C16 C15 178.7(4) . . . . ?
C12 C11 C16 C15 -56.6(5) . . . . ?
C14 C15 C16 C11 55.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 I1 0.98(4) 2.83(4) 3.726(4) 152(3) 1_655

_refine_diff_density_max         0.499
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.111

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 1017140'
#######################################################################
#
#                 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_a31202a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C67 H70 Cl2 I2 N4 O'
_chemical_formula_weight         1271.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.894(7)
_cell_length_b                   15.126(7)
_cell_length_c                   17.283(8)
_cell_angle_alpha                108.209(5)
_cell_angle_beta                 97.011(6)
_cell_angle_gamma                114.943(5)
_cell_volume                     2990(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    959
_cell_measurement_theta_min      2.596
_cell_measurement_theta_max      26.112

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.187
_shelx_estimated_absorpt_T_min   0.681
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.477
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12435
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.617
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             10298
_reflns_number_gt                7623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0842P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10298
_refine_ls_number_parameters     698
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1228
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 -0.00860(3) 0.65149(2) 0.25878(2) 0.06349(12) Uani 1 1 d . . . . .
I2 I 0.28444(3) 0.04185(3) 0.24997(2) 0.07638(13) Uani 1 1 d . . . . .
N1 N 0.1065(2) 0.8503(2) 0.94993(18) 0.0423(7) Uani 1 1 d . . . . .
N2 N 0.0697(2) 0.6946(2) 0.95025(18) 0.0417(7) Uani 1 1 d . . . . .
N3 N 0.4134(2) 0.1805(2) 0.55768(19) 0.0453(7) Uani 1 1 d . . . . .
N4 N 0.2400(2) 0.1228(2) 0.55792(18) 0.0432(7) Uani 1 1 d . . . . .
C1 C 0.0971(3) 0.7561(3) 0.9079(2) 0.0402(8) Uani 1 1 d . . . . .
C2 C 0.0682(3) 0.8518(3) 1.0271(2) 0.0505(9) Uani 1 1 d . . . . .
H2A H -0.0025 0.8511 1.0200 0.061 Uiso 1 1 calc R U . . .
H2B H 0.1223 0.9140 1.0776 0.061 Uiso 1 1 calc R U . . .
C3 C 0.0572(3) 0.7509(3) 1.0327(2) 0.0465(9) Uani 1 1 d . . . . .
H3 H 0.1184 0.7685 1.0798 0.056 Uiso 1 1 calc R U . . .
C4 C -0.0512(3) 0.6694(3) 1.0362(2) 0.0473(9) Uani 1 1 d . . . . .
H4A H -0.0956 0.7021 1.0554 0.057 Uiso 1 1 calc R U . . .
H4B H -0.0372 0.6388 1.0751 0.057 Uiso 1 1 calc R U . . .
C5 C -0.1120(3) 0.5822(3) 0.9440(2) 0.0416(8) Uani 1 1 d . . . . .
C6 C -0.0111(3) 0.5805(3) 0.9156(2) 0.0437(8) Uani 1 1 d . . . . .
H6A H 0.0162 0.5427 0.9399 0.052 Uiso 1 1 calc R U . . .
H6B H -0.0293 0.5482 0.8540 0.052 Uiso 1 1 calc R U . . .
C7 C 0.1161(3) 0.7225(3) 0.8240(2) 0.0433(8) Uani 1 1 d . . . . .
C8 C 0.0940(3) 0.7592(3) 0.7641(2) 0.0540(9) Uani 1 1 d . . . . .
H8 H 0.0667 0.8069 0.7760 0.065 Uiso 1 1 calc R U . . .
C9 C 0.1125(4) 0.7249(3) 0.6865(3) 0.0609(11) Uani 1 1 d . . . . .
H9 H 0.0986 0.7502 0.6463 0.073 Uiso 1 1 calc R U . . .
C10 C 0.1514(4) 0.6537(4) 0.6684(3) 0.0638(11) Uani 1 1 d . . . . .
H10 H 0.1645 0.6313 0.6161 0.077 Uiso 1 1 calc R U . . .
C11 C 0.1708(4) 0.6156(3) 0.7263(3) 0.0642(12) Uani 1 1 d . . . . .
H11 H 0.1953 0.5657 0.7128 0.077 Uiso 1 1 calc R U . . .
C12 C 0.1549(3) 0.6499(3) 0.8053(3) 0.0519(9) Uani 1 1 d . . . . .
H12 H 0.1700 0.6246 0.8452 0.062 Uiso 1 1 calc R U . . .
C13 C 0.1633(3) 0.9469(3) 0.9370(2) 0.0443(8) Uani 1 1 d . . . . .
C14 C 0.1009(3) 0.9829(3) 0.9019(2) 0.0484(9) Uani 1 1 d . . . . .
C15 C 0.1583(4) 1.0775(3) 0.8912(3) 0.0570(11) Uani 1 1 d . . . . .
H15 H 0.1187 1.1036 0.8669 0.068 Uiso 1 1 calc R U . . .
C16 C 0.2737(4) 1.1329(3) 0.9162(3) 0.0637(12) Uani 1 1 d . . . . .
C17 C 0.3303(4) 1.0942(3) 0.9520(3) 0.0618(11) Uani 1 1 d . . . . .
H17 H 0.4075 1.1322 0.9694 0.074 Uiso 1 1 calc R U . . .
C18 C 0.2786(3) 1.0011(3) 0.9638(2) 0.0517(9) Uani 1 1 d . . . . .
C19 C -0.0241(3) 0.9231(3) 0.8748(3) 0.0598(10) Uani 1 1 d . . . . .
H19A H -0.0500 0.8491 0.8414 0.090 Uiso 1 1 calc R U . . .
H19B H -0.0524 0.9518 0.8414 0.090 Uiso 1 1 calc R U . . .
H19C H -0.0496 0.9302 0.9245 0.090 Uiso 1 1 calc R U . . .
C20 C 0.3320(5) 1.2333(4) 0.9029(4) 0.0896(17) Uani 1 1 d . . . . .
H20A H 0.3703 1.2930 0.9572 0.134 Uiso 1 1 calc R U . . .
H20B H 0.2786 1.2424 0.8702 0.134 Uiso 1 1 calc R U . . .
H20C H 0.3846 1.2288 0.8728 0.134 Uiso 1 1 calc R U . . .
C21 C 0.3437(4) 0.9607(4) 1.0034(3) 0.0728(13) Uani 1 1 d . . . . .
H21A H 0.3240 0.9546 1.0535 0.109 Uiso 1 1 calc R U . . .
H21B H 0.4216 1.0094 1.0186 0.109 Uiso 1 1 calc R U . . .
H21C H 0.3272 0.8920 0.9634 0.109 Uiso 1 1 calc R U . . .
C22 C -0.1922(3) 0.4745(3) 0.9421(2) 0.0460(8) Uani 1 1 d . . . . .
C23 C -0.2128(3) 0.3799(3) 0.8789(3) 0.0538(9) Uani 1 1 d . . . . .
H23 H -0.1763 0.3820 0.8373 0.065 Uiso 1 1 calc R U . . .
C24 C -0.2871(4) 0.2824(3) 0.8770(3) 0.0651(11) Uani 1 1 d . . . . .
H24 H -0.3001 0.2196 0.8342 0.078 Uiso 1 1 calc R U . . .
C25 C -0.3413(4) 0.2785(4) 0.9377(3) 0.0701(13) Uani 1 1 d . . . . .
H25 H -0.3916 0.2130 0.9361 0.084 Uiso 1 1 calc R U . . .
C26 C -0.3217(4) 0.3693(4) 0.9996(3) 0.0779(14) Uani 1 1 d . . . . .
H26 H -0.3583 0.3659 1.0410 0.094 Uiso 1 1 calc R U . . .
C27 C -0.2484(4) 0.4674(4) 1.0030(3) 0.0628(11) Uani 1 1 d . . . . .
H27 H -0.2364 0.5293 1.0464 0.075 Uiso 1 1 calc R U . . .
C28 C -0.1736(3) 0.6137(3) 0.8879(2) 0.0415(8) Uani 1 1 d . . . . .
C29 C -0.1893(4) 0.5772(4) 0.8011(2) 0.0635(11) Uani 1 1 d . . . . .
H29 H -0.1620 0.5323 0.7761 0.076 Uiso 1 1 calc R U . . .
C30 C -0.2449(4) 0.6063(4) 0.7507(3) 0.0779(14) Uani 1 1 d . . . . .
H30 H -0.2537 0.5814 0.6924 0.093 Uiso 1 1 calc R U . . .
C31 C -0.2870(4) 0.6709(4) 0.7853(3) 0.0700(12) Uani 1 1 d . . . . .
H31 H -0.3241 0.6905 0.7512 0.084 Uiso 1 1 calc R U . . .
C32 C -0.2740(4) 0.7057(4) 0.8691(3) 0.0730(13) Uani 1 1 d . . . . .
H32 H -0.3023 0.7500 0.8933 0.088 Uiso 1 1 calc R U . . .
C33 C -0.2196(3) 0.6772(3) 0.9203(3) 0.0585(10) Uani 1 1 d . . . . .
H33 H -0.2136 0.7011 0.9781 0.070 Uiso 1 1 calc R U . . .
C34 C 0.3449(3) 0.1959(3) 0.6005(2) 0.0410(8) Uani 1 1 d . . . . .
C35 C 0.3526(3) 0.0775(3) 0.4817(2) 0.0516(9) Uani 1 1 d . . . . .
H35A H 0.3677 0.0239 0.4907 0.062 Uiso 1 1 calc R U . . .
H35B H 0.3720 0.0858 0.4314 0.062 Uiso 1 1 calc R U . . .
C36 C 0.2315(3) 0.0487(3) 0.4737(2) 0.0471(8) Uani 1 1 d . . . . .
H36 H 0.2025 0.0644 0.4281 0.057 Uiso 1 1 calc R U . . .
C37 C 0.1494(3) -0.0604(3) 0.4660(2) 0.0482(9) Uani 1 1 d . . . . .
H37A H 0.1746 -0.1113 0.4434 0.058 Uiso 1 1 calc R U . . .
H37B H 0.0772 -0.0852 0.4284 0.058 Uiso 1 1 calc R U . . .
C38 C 0.1425(3) -0.0477(3) 0.5580(2) 0.0414(8) Uani 1 1 d . . . . .
C39 C 0.1543(3) 0.0658(3) 0.5919(2) 0.0440(8) Uani 1 1 d . . . . .
H39A H 0.0851 0.0636 0.5705 0.053 Uiso 1 1 calc R U . . .
H39B H 0.1775 0.0984 0.6537 0.053 Uiso 1 1 calc R U . . .
C40 C 0.3772(3) 0.2837(3) 0.6820(2) 0.0438(8) Uani 1 1 d . . . . .
C41 C 0.3025(3) 0.3209(3) 0.7010(3) 0.0532(9) Uani 1 1 d . . . . .
H41 H 0.2332 0.2898 0.6618 0.064 Uiso 1 1 calc R U . . .
C42 C 0.3315(4) 0.4028(3) 0.7769(3) 0.0661(12) Uani 1 1 d . . . . .
H42 H 0.2812 0.4264 0.7896 0.079 Uiso 1 1 calc R U . . .
C43 C 0.4330(4) 0.4508(3) 0.8347(3) 0.0676(12) Uani 1 1 d . . . . .
H43 H 0.4522 0.5078 0.8856 0.081 Uiso 1 1 calc R U . . .
C44 C 0.5072(4) 0.4148(3) 0.8178(3) 0.0628(11) Uani 1 1 d . . . . .
H44 H 0.5761 0.4470 0.8578 0.075 Uiso 1 1 calc R U . . .
C45 C 0.4799(3) 0.3311(3) 0.7418(2) 0.0537(10) Uani 1 1 d . . . . .
H45 H 0.5299 0.3065 0.7307 0.064 Uiso 1 1 calc R U . . .
C46 C 0.5263(3) 0.2533(3) 0.5685(2) 0.0448(8) Uani 1 1 d . . . . .
C47 C 0.6110(3) 0.2371(3) 0.6045(2) 0.0488(9) Uani 1 1 d . . . . .
C48 C 0.7175(3) 0.3042(3) 0.6094(2) 0.0552(10) Uani 1 1 d . . . . .
H48 H 0.7750 0.2962 0.6341 0.066 Uiso 1 1 calc R U . . .
C49 C 0.7430(3) 0.3832(3) 0.5793(3) 0.0585(11) Uani 1 1 d . . . . .
C50 C 0.6577(4) 0.3945(3) 0.5429(3) 0.0580(10) Uani 1 1 d . . . . .
H50 H 0.6737 0.4467 0.5215 0.070 Uiso 1 1 calc R U . . .
C51 C 0.5480(3) 0.3299(3) 0.5373(3) 0.0530(10) Uani 1 1 d . . . . .
C52 C 0.5862(4) 0.1499(4) 0.6343(3) 0.0692(12) Uani 1 1 d . . . . .
H52A H 0.6544 0.1590 0.6651 0.104 Uiso 1 1 calc R U . . .
H52B H 0.5484 0.0825 0.5861 0.104 Uiso 1 1 calc R U . . .
H52C H 0.5398 0.1520 0.6710 0.104 Uiso 1 1 calc R U . . .
C53 C 0.8618(4) 0.4543(4) 0.5859(3) 0.0844(15) Uani 1 1 d . . . . .
H53A H 0.8639 0.4986 0.5559 0.127 Uiso 1 1 calc R U . . .
H53B H 0.8938 0.4112 0.5612 0.127 Uiso 1 1 calc R U . . .
H53C H 0.9035 0.4984 0.6448 0.127 Uiso 1 1 calc R U . . .
C54 C 0.4549(4) 0.3443(4) 0.4977(3) 0.0712(12) Uani 1 1 d . . . . .
H54A H 0.4011 0.2788 0.4509 0.107 Uiso 1 1 calc R U . . .
H54B H 0.4848 0.3997 0.4776 0.107 Uiso 1 1 calc R U . . .
H54C H 0.4198 0.3634 0.5397 0.107 Uiso 1 1 calc R U . . .
C55 C 0.2390(3) -0.0497(3) 0.6101(2) 0.0413(8) Uani 1 1 d . . . . .
C56 C 0.2866(3) 0.0118(4) 0.6958(2) 0.0601(11) Uani 1 1 d . . . . .
H56 H 0.2609 0.0568 0.7235 0.072 Uiso 1 1 calc R U . . .
C57 C 0.3724(4) 0.0080(4) 0.7418(3) 0.0722(13) Uani 1 1 d . . . . .
H57 H 0.4041 0.0511 0.7998 0.087 Uiso 1 1 calc R U . . .
C58 C 0.4111(4) -0.0580(4) 0.7034(3) 0.0674(12) Uani 1 1 d . . . . .
H58 H 0.4693 -0.0599 0.7345 0.081 Uiso 1 1 calc R U . . .
C59 C 0.3629(4) -0.1212(4) 0.6185(3) 0.0646(12) Uani 1 1 d . . . . .
H59 H 0.3883 -0.1669 0.5914 0.078 Uiso 1 1 calc R U . . .
C60 C 0.2769(3) -0.1183(3) 0.5724(2) 0.0536(10) Uani 1 1 d . . . . .
H60 H 0.2439 -0.1633 0.5149 0.064 Uiso 1 1 calc R U . . .
C61 C 0.0328(3) -0.1319(3) 0.5582(2) 0.0438(8) Uani 1 1 d . . . . .
C62 C -0.0133(3) -0.1099(3) 0.6238(3) 0.0535(9) Uani 1 1 d . . . . .
H62 H 0.0220 -0.0420 0.6674 0.064 Uiso 1 1 calc R U . . .
C63 C -0.1106(4) -0.1876(4) 0.6249(3) 0.0626(11) Uani 1 1 d . . . . .
H63 H -0.1408 -0.1714 0.6689 0.075 Uiso 1 1 calc R U . . .
C64 C -0.1639(4) -0.2891(4) 0.5616(3) 0.0674(12) Uani 1 1 d . . . . .
H64 H -0.2296 -0.3416 0.5625 0.081 Uiso 1 1 calc R U . . .
C65 C -0.1183(4) -0.3109(4) 0.4978(3) 0.0680(12) Uani 1 1 d . . . . .
H65 H -0.1534 -0.3793 0.4548 0.082 Uiso 1 1 calc R U . . .
C66 C -0.0212(3) -0.2341(3) 0.4952(3) 0.0570(10) Uani 1 1 d . . . . .
H66 H 0.0083 -0.2512 0.4509 0.068 Uiso 1 1 calc R U . . .
C67 C 0.4493(5) 0.7118(6) 0.7266(5) 0.129(3) Uani 1 1 d . U . . .
H67A H 0.3948 0.7292 0.7049 0.155 Uiso 1 1 calc R U . . .
H67B H 0.5200 0.7569 0.7209 0.155 Uiso 1 1 calc R U . . .
Cl1 Cl 0.46211(17) 0.73537(19) 0.83874(13) 0.1438(7) Uani 1 1 d . . . . .
Cl2 Cl 0.40949(15) 0.58294(16) 0.67051(12) 0.1207(6) Uani 1 1 d . . . . .
O1 O -0.0016(4) 0.8808(4) 0.2434(3) 0.1098(14) Uani 1 1 d D . . . .
H1A H -0.007(4) 0.832(3) 0.255(3) 0.079(17) Uiso 1 1 d D . . . .
H1B H 0.034(5) 0.887(5) 0.210(4) 0.119 Uiso 1 1 d D U . . .


_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 1.323(4) . ?
N1 C13 1.444(5) . ?
N1 C2 1.493(4) . ?
N2 C1 1.319(5) . ?
N2 C6 1.467(5) . ?
N2 C3 1.488(4) . ?
N3 C34 1.326(4) . ?
N3 C46 1.432(5) . ?
N3 C35 1.485(5) . ?
N4 C34 1.326(4) . ?
N4 C39 1.458(5) . ?
N4 C36 1.488(4) . ?
C1 C7 1.475(5) . ?
C2 C3 1.504(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.515(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.553(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C22 1.525(5) . ?
C5 C28 1.526(5) . ?
C5 C6 1.549(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.379(5) . ?
C7 C12 1.387(5) . ?
C8 C9 1.376(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.354(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.376(5) . ?
C13 C18 1.388(5) . ?
C14 C15 1.399(6) . ?
C14 C19 1.505(6) . ?
C15 C16 1.389(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.356(7) . ?
C16 C20 1.497(6) . ?
C17 C18 1.379(6) . ?
C17 H17 0.9300 . ?
C18 C21 1.495(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.387(5) . ?
C22 C27 1.388(5) . ?
C23 C24 1.385(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.366(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.342(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.378(6) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.380(5) . ?
C28 C33 1.384(5) . ?
C29 C30 1.382(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.363(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.338(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.375(6) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C40 1.458(5) . ?
C35 C36 1.525(5) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.511(5) . ?
C36 H36 0.9800 . ?
C37 C38 1.560(5) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C61 1.521(5) . ?
C38 C55 1.538(5) . ?
C38 C39 1.558(5) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C45 1.390(5) . ?
C40 C41 1.401(5) . ?
C41 C42 1.361(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.361(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.375(6) . ?
C43 H43 0.9300 . ?
C44 C45 1.381(5) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C46 C51 1.362(5) . ?
C46 C47 1.411(5) . ?
C47 C48 1.370(6) . ?
C47 C52 1.487(6) . ?
C48 C49 1.379(6) . ?
C48 H48 0.9300 . ?
C49 C50 1.373(6) . ?
C49 C53 1.508(6) . ?
C50 C51 1.393(6) . ?
C50 H50 0.9300 . ?
C51 C54 1.518(6) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C55 C56 1.370(5) . ?
C55 C60 1.379(5) . ?
C56 C57 1.382(6) . ?
C56 H56 0.9300 . ?
C57 C58 1.361(6) . ?
C57 H57 0.9300 . ?
C58 C59 1.364(6) . ?
C58 H58 0.9300 . ?
C59 C60 1.377(6) . ?
C59 H59 0.9300 . ?
C60 H60 0.9300 . ?
C61 C66 1.382(5) . ?
C61 C62 1.387(5) . ?
C62 C63 1.374(6) . ?
C62 H62 0.9300 . ?
C63 C64 1.377(6) . ?
C63 H63 0.9300 . ?
C64 C65 1.359(7) . ?
C64 H64 0.9300 . ?
C65 C66 1.376(6) . ?
C65 H65 0.9300 . ?
C66 H66 0.9300 . ?
C67 Cl2 1.681(8) . ?
C67 Cl1 1.830(8) . ?
C67 H67A 0.9700 . ?
C67 H67B 0.9700 . ?
O1 H1A 0.795(19) . ?
O1 H1B 0.810(19) . ?

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 C13 127.8(3) . . ?
C1 N1 C2 110.0(3) . . ?
C13 N1 C2 121.2(3) . . ?
C1 N2 C6 127.2(3) . . ?
C1 N2 C3 110.5(3) . . ?
C6 N2 C3 109.9(3) . . ?
C34 N3 C46 129.1(3) . . ?
C34 N3 C35 110.6(3) . . ?
C46 N3 C35 119.6(3) . . ?
C34 N4 C39 127.4(3) . . ?
C34 N4 C36 111.0(3) . . ?
C39 N4 C36 110.0(3) . . ?
N2 C1 N1 112.1(3) . . ?
N2 C1 C7 123.2(3) . . ?
N1 C1 C7 124.7(3) . . ?
N1 C2 C3 102.9(3) . . ?
N1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
N1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
N2 C3 C2 103.2(3) . . ?
N2 C3 C4 104.0(3) . . ?
C2 C3 C4 120.5(3) . . ?
N2 C3 H3 109.5 . . ?
C2 C3 H3 109.5 . . ?
C4 C3 H3 109.5 . . ?
C3 C4 C5 106.0(3) . . ?
C3 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C22 C5 C28 109.6(3) . . ?
C22 C5 C6 111.5(3) . . ?
C28 C5 C6 111.0(3) . . ?
C22 C5 C4 112.2(3) . . ?
C28 C5 C4 112.5(3) . . ?
C6 C5 C4 99.8(3) . . ?
N2 C6 C5 101.7(3) . . ?
N2 C6 H6A 111.4 . . ?
C5 C6 H6A 111.4 . . ?
N2 C6 H6B 111.4 . . ?
C5 C6 H6B 111.4 . . ?
H6A C6 H6B 109.3 . . ?
C8 C7 C12 119.8(3) . . ?
C8 C7 C1 122.0(3) . . ?
C12 C7 C1 118.1(3) . . ?
C9 C8 C7 119.7(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.9(4) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C7 119.0(4) . . ?
C11 C12 H12 120.5 . . ?
C7 C12 H12 120.5 . . ?
C14 C13 C18 123.3(4) . . ?
C14 C13 N1 118.6(3) . . ?
C18 C13 N1 118.1(3) . . ?
C13 C14 C15 117.3(4) . . ?
C13 C14 C19 121.9(3) . . ?
C15 C14 C19 120.8(4) . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 118.9(4) . . ?
C17 C16 C20 121.9(5) . . ?
C15 C16 C20 119.2(5) . . ?
C16 C17 C18 123.0(4) . . ?
C16 C17 H17 118.5 . . ?
C18 C17 H17 118.5 . . ?
C17 C18 C13 116.6(4) . . ?
C17 C18 C21 121.6(4) . . ?
C13 C18 C21 121.8(4) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 117.5(4) . . ?
C23 C22 C5 121.2(3) . . ?
C27 C22 C5 121.3(3) . . ?
C24 C23 C22 120.8(4) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 120.0(4) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 119.8(4) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 121.4(4) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C26 C27 C22 120.4(4) . . ?
C26 C27 H27 119.8 . . ?
C22 C27 H27 119.8 . . ?
C29 C28 C33 116.4(3) . . ?
C29 C28 C5 121.4(3) . . ?
C33 C28 C5 122.2(3) . . ?
C28 C29 C30 121.0(4) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C31 C30 C29 120.9(4) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C32 C31 C30 118.8(4) . . ?
C32 C31 H31 120.6 . . ?
C30 C31 H31 120.6 . . ?
C31 C32 C33 121.2(4) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C32 C33 C28 121.6(4) . . ?
C32 C33 H33 119.2 . . ?
C28 C33 H33 119.2 . . ?
N4 C34 N3 111.3(3) . . ?
N4 C34 C40 122.9(3) . . ?
N3 C34 C40 125.7(3) . . ?
N3 C35 C36 102.5(3) . . ?
N3 C35 H35A 111.3 . . ?
C36 C35 H35A 111.3 . . ?
N3 C35 H35B 111.3 . . ?
C36 C35 H35B 111.3 . . ?
H35A C35 H35B 109.2 . . ?
N4 C36 C37 104.3(3) . . ?
N4 C36 C35 102.1(3) . . ?
C37 C36 C35 119.7(3) . . ?
N4 C36 H36 110.0 . . ?
C37 C36 H36 110.0 . . ?
C35 C36 H36 110.0 . . ?
C36 C37 C38 106.1(3) . . ?
C36 C37 H37A 110.5 . . ?
C38 C37 H37A 110.5 . . ?
C36 C37 H37B 110.5 . . ?
C38 C37 H37B 110.5 . . ?
H37A C37 H37B 108.7 . . ?
C61 C38 C55 109.4(3) . . ?
C61 C38 C39 112.4(3) . . ?
C55 C38 C39 111.1(3) . . ?
C61 C38 C37 112.5(3) . . ?
C55 C38 C37 112.0(3) . . ?
C39 C38 C37 99.2(3) . . ?
N4 C39 C38 102.6(3) . . ?
N4 C39 H39A 111.3 . . ?
C38 C39 H39A 111.3 . . ?
N4 C39 H39B 111.3 . . ?
C38 C39 H39B 111.3 . . ?
H39A C39 H39B 109.2 . . ?
C45 C40 C41 119.0(3) . . ?
C45 C40 C34 121.8(3) . . ?
C41 C40 C34 119.2(3) . . ?
C42 C41 C40 119.8(4) . . ?
C42 C41 H41 120.1 . . ?
C40 C41 H41 120.1 . . ?
C43 C42 C41 121.2(4) . . ?
C43 C42 H42 119.4 . . ?
C41 C42 H42 119.4 . . ?
C42 C43 C44 120.0(4) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C43 C44 C45 120.3(4) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C44 C45 C40 119.7(4) . . ?
C44 C45 H45 120.2 . . ?
C40 C45 H45 120.2 . . ?
C51 C46 C47 122.0(4) . . ?
C51 C46 N3 119.4(3) . . ?
C47 C46 N3 118.4(3) . . ?
C48 C47 C46 117.1(4) . . ?
C48 C47 C52 121.1(4) . . ?
C46 C47 C52 121.8(4) . . ?
C47 C48 C49 122.6(4) . . ?
C47 C48 H48 118.7 . . ?
C49 C48 H48 118.7 . . ?
C50 C49 C48 118.3(4) . . ?
C50 C49 C53 121.3(4) . . ?
C48 C49 C53 120.3(4) . . ?
C49 C50 C51 121.7(4) . . ?
C49 C50 H50 119.2 . . ?
C51 C50 H50 119.2 . . ?
C46 C51 C50 118.2(4) . . ?
C46 C51 C54 120.8(4) . . ?
C50 C51 C54 121.0(4) . . ?
C47 C52 H52A 109.5 . . ?
C47 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C47 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C49 C53 H53A 109.5 . . ?
C49 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C49 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C51 C54 H54A 109.5 . . ?
C51 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C51 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C56 C55 C60 117.4(3) . . ?
C56 C55 C38 121.9(3) . . ?
C60 C55 C38 120.6(3) . . ?
C55 C56 C57 121.1(4) . . ?
C55 C56 H56 119.5 . . ?
C57 C56 H56 119.5 . . ?
C58 C57 C56 120.9(4) . . ?
C58 C57 H57 119.6 . . ?
C56 C57 H57 119.6 . . ?
C57 C58 C59 118.6(4) . . ?
C57 C58 H58 120.7 . . ?
C59 C58 H58 120.7 . . ?
C58 C59 C60 120.8(4) . . ?
C58 C59 H59 119.6 . . ?
C60 C59 H59 119.6 . . ?
C59 C60 C55 121.2(4) . . ?
C59 C60 H60 119.4 . . ?
C55 C60 H60 119.4 . . ?
C66 C61 C62 118.0(4) . . ?
C66 C61 C38 120.9(3) . . ?
C62 C61 C38 121.1(3) . . ?
C63 C62 C61 120.6(4) . . ?
C63 C62 H62 119.7 . . ?
C61 C62 H62 119.7 . . ?
C62 C63 C64 120.9(4) . . ?
C62 C63 H63 119.6 . . ?
C64 C63 H63 119.6 . . ?
C65 C64 C63 118.5(4) . . ?
C65 C64 H64 120.7 . . ?
C63 C64 H64 120.7 . . ?
C64 C65 C66 121.5(4) . . ?
C64 C65 H65 119.2 . . ?
C66 C65 H65 119.2 . . ?
C65 C66 C61 120.5(4) . . ?
C65 C66 H66 119.8 . . ?
C61 C66 H66 119.8 . . ?
Cl2 C67 Cl1 109.0(3) . . ?
Cl2 C67 H67A 109.9 . . ?
Cl1 C67 H67A 109.9 . . ?
Cl2 C67 H67B 109.9 . . ?
Cl1 C67 H67B 109.9 . . ?
H67A C67 H67B 108.3 . . ?
H1A O1 H1B 110(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 C1 N1 137.9(3) . . . . ?
C3 N2 C1 N1 0.3(4) . . . . ?
C6 N2 C1 C7 -42.8(5) . . . . ?
C3 N2 C1 C7 179.6(3) . . . . ?
C13 N1 C1 N2 161.3(3) . . . . ?
C2 N1 C1 N2 -7.5(4) . . . . ?
C13 N1 C1 C7 -18.0(5) . . . . ?
C2 N1 C1 C7 173.2(3) . . . . ?
C1 N1 C2 C3 11.2(4) . . . . ?
C13 N1 C2 C3 -158.5(3) . . . . ?
C1 N2 C3 C2 6.8(4) . . . . ?
C6 N2 C3 C2 -138.4(3) . . . . ?
C1 N2 C3 C4 133.3(3) . . . . ?
C6 N2 C3 C4 -12.0(4) . . . . ?
N1 C2 C3 N2 -10.2(4) . . . . ?
N1 C2 C3 C4 -125.3(3) . . . . ?
N2 C3 C4 C5 -16.1(3) . . . . ?
C2 C3 C4 C5 98.7(4) . . . . ?
C3 C4 C5 C22 154.3(3) . . . . ?
C3 C4 C5 C28 -81.6(4) . . . . ?
C3 C4 C5 C6 36.1(3) . . . . ?
C1 N2 C6 C5 -103.0(4) . . . . ?
C3 N2 C6 C5 34.9(3) . . . . ?
C22 C5 C6 N2 -160.8(3) . . . . ?
C28 C5 C6 N2 76.7(3) . . . . ?
C4 C5 C6 N2 -42.1(3) . . . . ?
N2 C1 C7 C8 149.3(4) . . . . ?
N1 C1 C7 C8 -31.5(5) . . . . ?
N2 C1 C7 C12 -29.2(5) . . . . ?
N1 C1 C7 C12 150.0(4) . . . . ?
C12 C7 C8 C9 -1.2(6) . . . . ?
C1 C7 C8 C9 -179.6(4) . . . . ?
C7 C8 C9 C10 0.8(6) . . . . ?
C8 C9 C10 C11 0.7(7) . . . . ?
C9 C10 C11 C12 -1.8(7) . . . . ?
C10 C11 C12 C7 1.4(6) . . . . ?
C8 C7 C12 C11 0.1(6) . . . . ?
C1 C7 C12 C11 178.5(3) . . . . ?
C1 N1 C13 C14 109.2(4) . . . . ?
C2 N1 C13 C14 -83.2(4) . . . . ?
C1 N1 C13 C18 -73.4(5) . . . . ?
C2 N1 C13 C18 94.3(4) . . . . ?
C18 C13 C14 C15 1.8(5) . . . . ?
N1 C13 C14 C15 179.1(3) . . . . ?
C18 C13 C14 C19 -178.9(4) . . . . ?
N1 C13 C14 C19 -1.6(5) . . . . ?
C13 C14 C15 C16 -0.9(5) . . . . ?
C19 C14 C15 C16 179.9(4) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
C14 C15 C16 C20 179.4(4) . . . . ?
C15 C16 C17 C18 0.9(6) . . . . ?
C20 C16 C17 C18 -179.0(4) . . . . ?
C16 C17 C18 C13 0.0(6) . . . . ?
C16 C17 C18 C21 179.9(4) . . . . ?
C14 C13 C18 C17 -1.4(6) . . . . ?
N1 C13 C18 C17 -178.7(3) . . . . ?
C14 C13 C18 C21 178.7(4) . . . . ?
N1 C13 C18 C21 1.4(5) . . . . ?
C28 C5 C22 C23 86.2(4) . . . . ?
C6 C5 C22 C23 -37.1(5) . . . . ?
C4 C5 C22 C23 -148.1(4) . . . . ?
C28 C5 C22 C27 -93.0(4) . . . . ?
C6 C5 C22 C27 143.7(4) . . . . ?
C4 C5 C22 C27 32.7(5) . . . . ?
C27 C22 C23 C24 0.2(6) . . . . ?
C5 C22 C23 C24 -179.0(4) . . . . ?
C22 C23 C24 C25 0.1(7) . . . . ?
C23 C24 C25 C26 -0.5(7) . . . . ?
C24 C25 C26 C27 0.6(8) . . . . ?
C25 C26 C27 C22 -0.3(8) . . . . ?
C23 C22 C27 C26 -0.1(6) . . . . ?
C5 C22 C27 C26 179.1(4) . . . . ?
C22 C5 C28 C29 -84.1(4) . . . . ?
C6 C5 C28 C29 39.5(5) . . . . ?
C4 C5 C28 C29 150.4(4) . . . . ?
C22 C5 C28 C33 93.8(4) . . . . ?
C6 C5 C28 C33 -142.6(4) . . . . ?
C4 C5 C28 C33 -31.8(5) . . . . ?
C33 C28 C29 C30 2.1(7) . . . . ?
C5 C28 C29 C30 -179.9(4) . . . . ?
C28 C29 C30 C31 -0.8(8) . . . . ?
C29 C30 C31 C32 -0.3(8) . . . . ?
C30 C31 C32 C33 -0.2(8) . . . . ?
C31 C32 C33 C28 1.7(7) . . . . ?
C29 C28 C33 C32 -2.6(6) . . . . ?
C5 C28 C33 C32 179.4(4) . . . . ?
C39 N4 C34 N3 136.8(3) . . . . ?
C36 N4 C34 N3 -2.3(4) . . . . ?
C39 N4 C34 C40 -45.9(5) . . . . ?
C36 N4 C34 C40 175.1(3) . . . . ?
C46 N3 C34 N4 161.9(3) . . . . ?
C35 N3 C34 N4 -8.2(4) . . . . ?
C46 N3 C34 C40 -15.3(6) . . . . ?
C35 N3 C34 C40 174.5(3) . . . . ?
C34 N3 C35 C36 14.5(4) . . . . ?
C46 N3 C35 C36 -156.7(3) . . . . ?
C34 N4 C36 C37 136.3(3) . . . . ?
C39 N4 C36 C37 -10.0(4) . . . . ?
C34 N4 C36 C35 11.0(4) . . . . ?
C39 N4 C36 C35 -135.3(3) . . . . ?
N3 C35 C36 N4 -14.4(4) . . . . ?
N3 C35 C36 C37 -128.8(3) . . . . ?
N4 C36 C37 C38 -17.4(4) . . . . ?
C35 C36 C37 C38 95.8(4) . . . . ?
C36 C37 C38 C61 155.0(3) . . . . ?
C36 C37 C38 C55 -81.3(4) . . . . ?
C36 C37 C38 C39 36.0(3) . . . . ?
C34 N4 C39 C38 -106.2(4) . . . . ?
C36 N4 C39 C38 33.1(3) . . . . ?
C61 C38 C39 N4 -160.1(3) . . . . ?
C55 C38 C39 N4 76.9(3) . . . . ?
C37 C38 C39 N4 -41.1(3) . . . . ?
N4 C34 C40 C45 152.4(4) . . . . ?
N3 C34 C40 C45 -30.7(5) . . . . ?
N4 C34 C40 C41 -27.1(5) . . . . ?
N3 C34 C40 C41 149.8(4) . . . . ?
C45 C40 C41 C42 0.4(6) . . . . ?
C34 C40 C41 C42 179.9(4) . . . . ?
C40 C41 C42 C43 1.0(7) . . . . ?
C41 C42 C43 C44 -1.7(7) . . . . ?
C42 C43 C44 C45 0.9(7) . . . . ?
C43 C44 C45 C40 0.5(7) . . . . ?
C41 C40 C45 C44 -1.2(6) . . . . ?
C34 C40 C45 C44 179.3(4) . . . . ?
C34 N3 C46 C51 -77.7(5) . . . . ?
C35 N3 C46 C51 91.6(4) . . . . ?
C34 N3 C46 C47 107.9(4) . . . . ?
C35 N3 C46 C47 -82.7(4) . . . . ?
C51 C46 C47 C48 2.0(5) . . . . ?
N3 C46 C47 C48 176.2(3) . . . . ?
C51 C46 C47 C52 -176.8(4) . . . . ?
N3 C46 C47 C52 -2.6(5) . . . . ?
C46 C47 C48 C49 -1.5(5) . . . . ?
C52 C47 C48 C49 177.3(4) . . . . ?
C47 C48 C49 C50 0.0(6) . . . . ?
C47 C48 C49 C53 -179.6(4) . . . . ?
C48 C49 C50 C51 1.1(6) . . . . ?
C53 C49 C50 C51 -179.3(4) . . . . ?
C47 C46 C51 C50 -1.0(6) . . . . ?
N3 C46 C51 C50 -175.2(3) . . . . ?
C47 C46 C51 C54 179.0(4) . . . . ?
N3 C46 C51 C54 4.9(6) . . . . ?
C49 C50 C51 C46 -0.5(6) . . . . ?
C49 C50 C51 C54 179.4(4) . . . . ?
C61 C38 C55 C56 -90.2(4) . . . . ?
C39 C38 C55 C56 34.5(5) . . . . ?
C37 C38 C55 C56 144.4(4) . . . . ?
C61 C38 C55 C60 86.5(4) . . . . ?
C39 C38 C55 C60 -148.8(3) . . . . ?
C37 C38 C55 C60 -38.9(5) . . . . ?
C60 C55 C56 C57 2.4(6) . . . . ?
C38 C55 C56 C57 179.2(4) . . . . ?
C55 C56 C57 C58 -0.8(8) . . . . ?
C56 C57 C58 C59 -0.5(8) . . . . ?
C57 C58 C59 C60 0.1(7) . . . . ?
C58 C59 C60 C55 1.6(7) . . . . ?
C56 C55 C60 C59 -2.8(6) . . . . ?
C38 C55 C60 C59 -179.7(4) . . . . ?
C55 C38 C61 C66 -90.9(4) . . . . ?
C39 C38 C61 C66 145.2(4) . . . . ?
C37 C38 C61 C66 34.2(5) . . . . ?
C55 C38 C61 C62 85.9(4) . . . . ?
C39 C38 C61 C62 -38.1(5) . . . . ?
C37 C38 C61 C62 -149.0(3) . . . . ?
C66 C61 C62 C63 -0.9(6) . . . . ?
C38 C61 C62 C63 -177.8(4) . . . . ?
C61 C62 C63 C64 0.7(6) . . . . ?
C62 C63 C64 C65 -0.1(7) . . . . ?
C63 C64 C65 C66 -0.2(7) . . . . ?
C64 C65 C66 C61 -0.1(7) . . . . ?
C62 C61 C66 C65 0.6(6) . . . . ?
C38 C61 C66 C65 177.5(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2B I2 0.97 2.96 3.885(4) 159.2 1_566
C35 H35B I2 0.97 2.97 3.810(4) 145.3 .
C67 H67B I2 0.97 2.94 3.847(6) 156.4 2_666
O1 H1A I1 0.795(19) 2.75(2) 3.523(5) 166(5) .
O1 H1B I2 0.810(19) 3.10(6) 3.646(6) 127(6) 1_565

_refine_diff_density_max         0.773
_refine_diff_density_min         -1.067
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 1016877'
#######################################################################
#
#                 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.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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_mo_40708a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H39 I3 N2'
_chemical_formula_weight         880.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

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

_cell_length_a                   9.621(2)
_cell_length_b                   14.084(4)
_cell_length_c                   12.671(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.151(5)
_cell_angle_gamma                90
_cell_volume                     1716.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4748
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      26.85

_exptl_crystal_description       rod
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.757
_shelx_estimated_absorpt_T_min   0.339
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.570
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9133
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.633
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.925
_reflns_number_total             6215
_reflns_number_gt                5445
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_max     0.852
_reflns_Friedel_fraction_full    0.860

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.1481P)²+17.4192P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2240 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.120(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6215
_refine_ls_number_parameters     374
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.2449
_refine_ls_wR_factor_gt          0.2372
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.74131(13) 0.26499(10) 0.68158(15) 0.0493(4) Uani 1 1 d . . . . .
I2 I 0.75836(17) 0.19616(11) 0.46213(15) 0.0607(5) Uani 1 1 d . . . . .
I3 I 0.7172(3) 0.33102(13) 0.89582(16) 0.0759(7) Uani 1 1 d . . . . .
N1 N 0.3103(13) 0.3000(11) 0.4191(12) 0.028(3) Uani 1 1 d . . . . .
N2 N 0.3347(12) 0.3988(10) 0.5548(11) 0.024(3) Uani 1 1 d . . . . .
C1 C 0.3961(16) 0.3364(12) 0.4946(13) 0.027(3) Uani 1 1 d . . . . .
H1 H 0.4909 0.3186 0.5032 0.032 Uiso 1 1 calc R U . . .
C2 C 0.1615(16) 0.3356(13) 0.4330(11) 0.025(3) Uani 1 1 d . . . . .
H2 H 0.0989 0.2808 0.4482 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1816(15) 0.3976(14) 0.5349(13) 0.026(3) Uani 1 1 d . . . . .
H3 H 0.1443 0.4632 0.5240 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1280(17) 0.3541(13) 0.6353(14) 0.028(3) Uani 1 1 d . . . . .
H4A H 0.1244 0.2841 0.6292 0.034 Uiso 1 1 calc R U . . .
H4B H 0.0335 0.3779 0.6498 0.034 Uiso 1 1 calc R U . . .
C5 C 0.2340(18) 0.3849(14) 0.7267(13) 0.028(4) Uani 1 1 d . . . . .
C6 C 0.3640(19) 0.4247(15) 0.6645(13) 0.034(4) Uani 1 1 d . . . . .
H6A H 0.3719 0.4944 0.6724 0.041 Uiso 1 1 calc R U . . .
H6B H 0.4515 0.3948 0.6904 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3447(18) 0.2306(13) 0.3436(14) 0.030(4) Uani 1 1 d . . . . .
C8 C 0.3972(18) 0.2527(13) 0.2500(14) 0.030(4) Uani 1 1 d . . . . .
C9 C 0.420(3) 0.1788(14) 0.1759(15) 0.043(5) Uani 1 1 d . . . . .
H9 H 0.4614 0.1926 0.1100 0.051 Uiso 1 1 calc R U . . .
C10 C 0.383(3) 0.0875(18) 0.2003(18) 0.056(7) Uani 1 1 d . . . . .
H10 H 0.3940 0.0391 0.1490 0.067 Uiso 1 1 calc R U . . .
C11 C 0.3317(19) 0.0646(14) 0.2945(18) 0.038(4) Uani 1 1 d . . . . .
H11 H 0.3089 0.0004 0.3098 0.046 Uiso 1 1 calc R U . . .
C12 C 0.3114(17) 0.1361(13) 0.3711(14) 0.028(3) Uani 1 1 d . . . . .
C13 C 0.447(2) 0.3526(16) 0.2245(15) 0.041(4) Uani 1 1 d . . . . .
H13 H 0.4153 0.3954 0.2820 0.049 Uiso 1 1 calc R U . . .
C14 C 0.598(2) 0.3596(17) 0.2220(18) 0.048(5) Uani 1 1 d . . . . .
H14A H 0.6373 0.3430 0.2914 0.072 Uiso 1 1 calc R U . . .
H14B H 0.6242 0.4248 0.2041 0.072 Uiso 1 1 calc R U . . .
H14C H 0.6331 0.3159 0.1687 0.072 Uiso 1 1 calc R U . . .
C15 C 0.384(2) 0.3899(15) 0.1194(17) 0.039(4) Uani 1 1 d . . . . .
H15A H 0.3735 0.4591 0.1232 0.059 Uiso 1 1 calc R U . . .
H15B H 0.2923 0.3608 0.1071 0.059 Uiso 1 1 calc R U . . .
H15C H 0.4450 0.3736 0.0612 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2671(18) 0.1060(14) 0.4803(16) 0.035(4) Uani 1 1 d . . . . .
H16 H 0.2516 0.1649 0.5226 0.042 Uiso 1 1 calc R U . . .
C17 C 0.377(2) 0.048(2) 0.536(2) 0.056(6) Uani 1 1 d . . . . .
H17A H 0.3855 -0.0135 0.5016 0.084 Uiso 1 1 calc R U . . .
H17B H 0.3507 0.0388 0.6100 0.084 Uiso 1 1 calc R U . . .
H17C H 0.4659 0.0819 0.5343 0.084 Uiso 1 1 calc R U . . .
C18 C 0.130(2) 0.046(2) 0.481(2) 0.056(6) Uani 1 1 d . . . . .
H18A H 0.1455 -0.0156 0.4485 0.085 Uiso 1 1 calc R U . . .
H18B H 0.0562 0.0802 0.4421 0.085 Uiso 1 1 calc R U . . .
H18C H 0.1011 0.0370 0.5546 0.085 Uiso 1 1 calc R U . . .
C19 C 0.1083(15) 0.3880(12) 0.3343(13) 0.023(3) Uani 1 1 d . . . . .
C20 C 0.143(2) 0.4825(15) 0.3089(16) 0.037(4) Uani 1 1 d . . . . .
H20 H 0.2012 0.5181 0.3556 0.045 Uiso 1 1 calc R U . . .
C21 C 0.095(3) 0.5221(18) 0.2205(19) 0.054(6) Uani 1 1 d . . . . .
H21 H 0.1205 0.5855 0.2042 0.064 Uiso 1 1 calc R U . . .
C22 C 0.006(3) 0.471(2) 0.1499(18) 0.053(6) Uani 1 1 d . . . . .
H22 H -0.0285 0.5002 0.0870 0.064 Uiso 1 1 calc R U . . .
C23 C -0.030(2) 0.3780(18) 0.1735(16) 0.045(5) Uani 1 1 d . . . . .
H23 H -0.0929 0.3437 0.1289 0.054 Uiso 1 1 calc R U . . .
C24 C 0.028(2) 0.3357(16) 0.2654(16) 0.040(4) Uani 1 1 d . . . . .
H24 H 0.0109 0.2705 0.2795 0.048 Uiso 1 1 calc R U . . .
C25 C 0.2623(17) 0.2970(13) 0.7930(14) 0.028(3) Uani 1 1 d . . . . .
C26 C 0.191(3) 0.2775(15) 0.8822(18) 0.048(5) Uani 1 1 d . . . . .
H26 H 0.1259 0.3224 0.9073 0.057 Uiso 1 1 calc R U . . .
C27 C 0.212(3) 0.190(2) 0.939(2) 0.065(7) Uani 1 1 d . . . . .
H27 H 0.1583 0.1771 0.9991 0.078 Uiso 1 1 calc R U . . .
C28 C 0.313(4) 0.124(2) 0.906(2) 0.068(8) Uani 1 1 d . . . . .
H28 H 0.3304 0.0664 0.9434 0.082 Uiso 1 1 calc R U . . .
C29 C 0.383(2) 0.1482(18) 0.8190(19) 0.050(6) Uani 1 1 d . . . . .
H29 H 0.4539 0.1061 0.7967 0.061 Uiso 1 1 calc R U . . .
C30 C 0.361(2) 0.2263(16) 0.7615(19) 0.042(5) Uani 1 1 d . . . . .
H30 H 0.4119 0.2354 0.6987 0.050 Uiso 1 1 calc R U . . .
C31 C 0.182(2) 0.4689(14) 0.7951(14) 0.034(4) Uani 1 1 d . . . . .
C32 C 0.055(2) 0.5102(17) 0.7839(17) 0.044(5) Uani 1 1 d . . . . .
H32 H -0.0094 0.4865 0.7328 0.053 Uiso 1 1 calc R U . . .
C33 C 0.019(3) 0.589(2) 0.848(2) 0.068(8) Uani 1 1 d . . . . .
H33 H -0.0693 0.6184 0.8390 0.082 Uiso 1 1 calc R U . . .
C34 C 0.112(2) 0.621(2) 0.9222(18) 0.055(6) Uani 1 1 d . . . . .
H34 H 0.0873 0.6713 0.9679 0.065 Uiso 1 1 calc R U . . .
C35 C 0.242(3) 0.5809(18) 0.9311(18) 0.052(6) Uani 1 1 d . . . . .
H35 H 0.3071 0.6074 0.9802 0.063 Uiso 1 1 calc R U . . .
C36 C 0.281(2) 0.5043(16) 0.8720(15) 0.039(4) Uani 1 1 d . . . . .
H36 H 0.3702 0.4758 0.8812 0.047 Uiso 1 1 calc R U . . .


_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 I3 2.883(3) . ?
I1 I2 2.952(3) . ?
N1 C1 1.35(2) . ?
N1 C7 1.41(2) . ?
N1 C2 1.53(2) . ?
N2 C1 1.31(2) . ?
N2 C6 1.46(2) . ?
N2 C3 1.490(18) . ?
C2 C19 1.53(2) . ?
C2 C3 1.57(2) . ?
C3 C4 1.51(2) . ?
C4 C5 1.59(2) . ?
C5 C25 1.52(3) . ?
C5 C31 1.56(3) . ?
C5 C6 1.59(3) . ?
C7 C8 1.33(3) . ?
C7 C12 1.41(3) . ?
C8 C9 1.42(3) . ?
C8 C13 1.52(3) . ?
C9 C10 1.37(4) . ?
C10 C11 1.34(4) . ?
C11 C12 1.42(3) . ?
C12 C16 1.52(3) . ?
C13 C14 1.45(3) . ?
C13 C15 1.55(3) . ?
C16 C17 1.50(3) . ?
C16 C18 1.57(2) . ?
C19 C24 1.37(3) . ?
C19 C20 1.41(3) . ?
C20 C21 1.33(3) . ?
C21 C22 1.42(4) . ?
C22 C23 1.39(4) . ?
C23 C24 1.41(3) . ?
C25 C26 1.36(3) . ?
C25 C30 1.44(3) . ?
C26 C27 1.44(4) . ?
C27 C28 1.41(5) . ?
C28 C29 1.35(4) . ?
C29 C30 1.33(3) . ?
C31 C32 1.35(3) . ?
C31 C36 1.44(3) . ?
C32 C33 1.42(4) . ?
C33 C34 1.37(4) . ?
C34 C35 1.37(4) . ?
C35 C36 1.37(3) . ?

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
I3 I1 I2 178.54(8) . . ?
C1 N1 C7 126.4(14) . . ?
C1 N1 C2 110.7(13) . . ?
C7 N1 C2 122.5(14) . . ?
C1 N2 C6 129.8(15) . . ?
C1 N2 C3 110.4(13) . . ?
C6 N2 C3 109.7(13) . . ?
N2 C1 N1 112.9(14) . . ?
N1 C2 C19 111.2(12) . . ?
N1 C2 C3 100.2(12) . . ?
C19 C2 C3 116.0(15) . . ?
N2 C3 C4 102.4(13) . . ?
N2 C3 C2 104.6(13) . . ?
C4 C3 C2 115.4(14) . . ?
C3 C4 C5 106.2(13) . . ?
C25 C5 C31 111.6(14) . . ?
C25 C5 C4 106.7(15) . . ?
C31 C5 C4 113.8(15) . . ?
C25 C5 C6 115.2(15) . . ?
C31 C5 C6 105.9(15) . . ?
C4 C5 C6 103.5(13) . . ?
N2 C6 C5 104.2(14) . . ?
C8 C7 N1 122.6(17) . . ?
C8 C7 C12 122.0(16) . . ?
N1 C7 C12 115.2(15) . . ?
C7 C8 C9 118.9(18) . . ?
C7 C8 C13 122.1(16) . . ?
C9 C8 C13 118.7(16) . . ?
C10 C9 C8 119.4(18) . . ?
C11 C10 C9 122.0(19) . . ?
C10 C11 C12 119.8(19) . . ?
C11 C12 C7 117.7(17) . . ?
C11 C12 C16 118.2(17) . . ?
C7 C12 C16 123.9(15) . . ?
C14 C13 C8 112.9(19) . . ?
C14 C13 C15 109.6(16) . . ?
C8 C13 C15 112.0(17) . . ?
C17 C16 C12 112.1(15) . . ?
C17 C16 C18 106.9(19) . . ?
C12 C16 C18 114.3(18) . . ?
C24 C19 C20 119.7(17) . . ?
C24 C19 C2 115.9(17) . . ?
C20 C19 C2 124.3(15) . . ?
C21 C20 C19 121(2) . . ?
C20 C21 C22 121(2) . . ?
C23 C22 C21 119(2) . . ?
C22 C23 C24 119(2) . . ?
C19 C24 C23 120(2) . . ?
C26 C25 C30 115.9(18) . . ?
C26 C25 C5 122.5(18) . . ?
C30 C25 C5 121.6(16) . . ?
C25 C26 C27 121(2) . . ?
C28 C27 C26 121(2) . . ?
C29 C28 C27 115(2) . . ?
C30 C29 C28 125(2) . . ?
C29 C30 C25 121(2) . . ?
C32 C31 C36 120.4(19) . . ?
C32 C31 C5 124.6(17) . . ?
C36 C31 C5 114.9(18) . . ?
C31 C32 C33 120(2) . . ?
C34 C33 C32 119(2) . . ?
C33 C34 C35 120(2) . . ?
C34 C35 C36 123(2) . . ?
C35 C36 C31 117(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
C6 N2 C1 N1 151.8(17) . . . . ?
C3 N2 C1 N1 11(2) . . . . ?
C7 N1 C1 N2 -178.9(16) . . . . ?
C2 N1 C1 N2 -6(2) . . . . ?
C1 N1 C2 C19 121.6(16) . . . . ?
C7 N1 C2 C19 -65(2) . . . . ?
C1 N1 C2 C3 -1.6(17) . . . . ?
C7 N1 C2 C3 172.1(16) . . . . ?
C1 N2 C3 C4 109.7(16) . . . . ?
C6 N2 C3 C4 -39.4(18) . . . . ?
C1 N2 C3 C2 -11.1(19) . . . . ?
C6 N2 C3 C2 -160.2(15) . . . . ?
N1 C2 C3 N2 7.1(16) . . . . ?
C19 C2 C3 N2 -112.7(14) . . . . ?
N1 C2 C3 C4 -104.6(15) . . . . ?
C19 C2 C3 C4 135.6(14) . . . . ?
N2 C3 C4 C5 30.9(17) . . . . ?
C2 C3 C4 C5 143.8(14) . . . . ?
C3 C4 C5 C25 -135.4(15) . . . . ?
C3 C4 C5 C31 101.0(17) . . . . ?
C3 C4 C5 C6 -13.5(18) . . . . ?
C1 N2 C6 C5 -110.7(18) . . . . ?
C3 N2 C6 C5 30.6(19) . . . . ?
C25 C5 C6 N2 106.4(16) . . . . ?
C31 C5 C6 N2 -129.6(15) . . . . ?
C4 C5 C6 N2 -9.6(18) . . . . ?
C1 N1 C7 C8 -89(2) . . . . ?
C2 N1 C7 C8 99(2) . . . . ?
C1 N1 C7 C12 95(2) . . . . ?
C2 N1 C7 C12 -77(2) . . . . ?
N1 C7 C8 C9 -175.9(18) . . . . ?
C12 C7 C8 C9 0(3) . . . . ?
N1 C7 C8 C13 11(3) . . . . ?
C12 C7 C8 C13 -173.4(17) . . . . ?
C7 C8 C9 C10 3(3) . . . . ?
C13 C8 C9 C10 176(2) . . . . ?
C8 C9 C10 C11 -4(4) . . . . ?
C9 C10 C11 C12 2(3) . . . . ?
C10 C11 C12 C7 1(3) . . . . ?
C10 C11 C12 C16 -173.9(19) . . . . ?
C8 C7 C12 C11 -2(3) . . . . ?
N1 C7 C12 C11 174.3(15) . . . . ?
C8 C7 C12 C16 172.8(16) . . . . ?
N1 C7 C12 C16 -11(2) . . . . ?
C7 C8 C13 C14 107(2) . . . . ?
C9 C8 C13 C14 -67(2) . . . . ?
C7 C8 C13 C15 -129.0(18) . . . . ?
C9 C8 C13 C15 58(2) . . . . ?
C11 C12 C16 C17 65(2) . . . . ?
C7 C12 C16 C17 -109(2) . . . . ?
C11 C12 C16 C18 -57(2) . . . . ?
C7 C12 C16 C18 129(2) . . . . ?
N1 C2 C19 C24 97.5(17) . . . . ?
C3 C2 C19 C24 -148.8(15) . . . . ?
N1 C2 C19 C20 -79(2) . . . . ?
C3 C2 C19 C20 35(2) . . . . ?
C24 C19 C20 C21 2(3) . . . . ?
C2 C19 C20 C21 178.4(19) . . . . ?
C19 C20 C21 C22 1(4) . . . . ?
C20 C21 C22 C23 -1(4) . . . . ?
C21 C22 C23 C24 -3(4) . . . . ?
C20 C19 C24 C23 -5(3) . . . . ?
C2 C19 C24 C23 177.9(16) . . . . ?
C22 C23 C24 C19 6(3) . . . . ?
C31 C5 C25 C26 30(3) . . . . ?
C4 C5 C25 C26 -95(2) . . . . ?
C6 C5 C25 C26 150.8(19) . . . . ?
C31 C5 C25 C30 -153.7(17) . . . . ?
C4 C5 C25 C30 81(2) . . . . ?
C6 C5 C25 C30 -33(2) . . . . ?
C30 C25 C26 C27 -1(3) . . . . ?
C5 C25 C26 C27 175(2) . . . . ?
C25 C26 C27 C28 3(4) . . . . ?
C26 C27 C28 C29 -1(4) . . . . ?
C27 C28 C29 C30 -2(4) . . . . ?
C28 C29 C30 C25 4(4) . . . . ?
C26 C25 C30 C29 -2(3) . . . . ?
C5 C25 C30 C29 -178(2) . . . . ?
C25 C5 C31 C32 -117(2) . . . . ?
C4 C5 C31 C32 3(3) . . . . ?
C6 C5 C31 C32 117(2) . . . . ?
C25 C5 C31 C36 65(2) . . . . ?
C4 C5 C31 C36 -174.2(16) . . . . ?
C6 C5 C31 C36 -61(2) . . . . ?
C36 C31 C32 C33 0(3) . . . . ?
C5 C31 C32 C33 -178(2) . . . . ?
C31 C32 C33 C34 -1(4) . . . . ?
C32 C33 C34 C35 3(4) . . . . ?
C33 C34 C35 C36 -4(4) . . . . ?
C34 C35 C36 C31 3(3) . . . . ?
C32 C31 C36 C35 0(3) . . . . ?
C5 C31 C36 C35 177.3(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 I2 0.95 3.15 4.034(17) 155.7 .

_refine_diff_density_max         2.348
_refine_diff_density_min         -1.524
_refine_diff_density_rms         0.252

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 1017141'
#######################################################################
#
#                 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
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a40411a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 I N2'
_chemical_formula_weight         390.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

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

_cell_length_a                   6.6862(13)
_cell_length_b                   10.542(2)
_cell_length_c                   23.520(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1657.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3928
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      24.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.927
_shelx_estimated_absorpt_T_min   0.699
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8490
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.732
_diffrn_reflns_theta_max         25.783
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3086
_reflns_number_gt                2834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.977

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0263P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1095 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.003(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3086
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0530
_refine_ls_wR_factor_gt          0.0519
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.59179(4) 0.57163(3) 0.21696(2) 0.04860(12) Uani 1 1 d . . . . .
N1 N 0.0805(5) 0.7821(3) 0.28880(14) 0.0380(7) Uani 1 1 d . . . . .
N2 N 0.0633(5) 0.8699(3) 0.20490(13) 0.0369(8) Uani 1 1 d . . . . .
C1 C 0.1697(7) 0.8043(4) 0.23987(19) 0.0379(10) Uani 1 1 d . . . . .
C2 C -0.1132(6) 0.9213(5) 0.23443(17) 0.0461(10) Uani 1 1 d . . . . .
H2A H -0.2346 0.9045 0.2131 0.055 Uiso 1 1 calc R U . . .
H2B H -0.1006 1.0121 0.2403 0.055 Uiso 1 1 calc R U . . .
C3 C -0.1133(6) 0.8507(4) 0.29071(18) 0.0429(10) Uani 1 1 d . . . . .
H3 H -0.2240 0.7898 0.2917 0.052 Uiso 1 1 calc R U . . .
C4 C -0.1019(7) 0.9223(5) 0.34715(19) 0.0510(10) Uani 1 1 d . . . . .
H4A H -0.0655 1.0104 0.3412 0.061 Uiso 1 1 calc R U . . .
H4B H -0.2287 0.9189 0.3671 0.061 Uiso 1 1 calc R U . . .
C5 C 0.0582(7) 0.8532(4) 0.37949(19) 0.0437(11) Uani 1 1 d . . . . .
C6 C 0.1168(9) 0.8625(5) 0.4351(2) 0.0612(13) Uani 1 1 d . . . . .
H6 H 0.0462 0.9133 0.4604 0.073 Uiso 1 1 calc R U . . .
C7 C 0.2824(9) 0.7952(6) 0.4530(2) 0.0680(16) Uani 1 1 d . . . . .
H7 H 0.3241 0.8017 0.4906 0.082 Uiso 1 1 calc R U . . .
C8 C 0.3857(9) 0.7193(5) 0.4163(2) 0.0648(14) Uani 1 1 d . . . . .
H8 H 0.4965 0.6746 0.4294 0.078 Uiso 1 1 calc R U . . .
C9 C 0.3292(7) 0.7077(5) 0.3604(2) 0.0537(12) Uani 1 1 d . . . . .
H9 H 0.3996 0.6563 0.3353 0.064 Uiso 1 1 calc R U . . .
C10 C 0.1649(6) 0.7749(4) 0.34336(19) 0.0403(10) Uani 1 1 d . . . . .
C11 C 0.1262(5) 0.9212(4) 0.15001(17) 0.0399(9) Uani 1 1 d . . . . .
H11 H 0.1318 1.0138 0.1535 0.048 Uiso 1 1 calc R U . . .
C12 C -0.0224(6) 0.8896(4) 0.10388(18) 0.0409(11) Uani 1 1 d . . . . .
C13 C -0.1300(7) 0.7791(5) 0.1038(2) 0.0512(12) Uani 1 1 d . . . . .
H13 H -0.1201 0.7232 0.1342 0.061 Uiso 1 1 calc R U . . .
C14 C -0.2528(8) 0.7507(6) 0.0586(3) 0.0709(18) Uani 1 1 d . . . . .
H14 H -0.3279 0.6764 0.0588 0.085 Uiso 1 1 calc R U . . .
C15 C -0.2642(9) 0.8319(9) 0.0134(3) 0.084(2) Uani 1 1 d . . . . .
H15 H -0.3446 0.8116 -0.0176 0.101 Uiso 1 1 calc R U . . .
C16 C -0.1585(9) 0.9426(7) 0.0134(2) 0.0790(18) Uani 1 1 d . . . . .
H16 H -0.1677 0.9981 -0.0172 0.095 Uiso 1 1 calc R U . . .
C17 C -0.0390(8) 0.9712(5) 0.0587(2) 0.0621(14) Uani 1 1 d . . . . .
H17 H 0.0321 1.0470 0.0589 0.075 Uiso 1 1 calc R U . . .
C18 C 0.3345(6) 0.8748(6) 0.1338(2) 0.0564(14) Uani 1 1 d . . . . .
H18A H 0.4282 0.8993 0.1627 0.085 Uiso 1 1 calc R U . . .
H18B H 0.3731 0.9118 0.0982 0.085 Uiso 1 1 calc R U . . .
H18C H 0.3333 0.7841 0.1304 0.085 Uiso 1 1 calc R U . . .
H1 H 0.293(7) 0.767(4) 0.231(2) 0.054(14) Uiso 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 1.317(5) . ?
N1 C10 1.404(5) . ?
N1 C3 1.484(5) . ?
N2 C1 1.289(5) . ?
N2 C11 1.461(5) . ?
N2 C2 1.473(5) . ?
C1 H1 0.93(5) . ?
C2 C3 1.519(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.529(6) . ?
C3 H3 0.9800 . ?
C4 C5 1.502(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.369(6) . ?
C5 C10 1.383(6) . ?
C6 C7 1.381(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.364(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(6) . ?
C9 H9 0.9300 . ?
C11 C12 1.509(6) . ?
C11 C18 1.524(6) . ?
C11 H11 0.9800 . ?
C12 C13 1.369(6) . ?
C12 C17 1.371(6) . ?
C13 C14 1.376(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C10 128.8(4) . . ?
C1 N1 C3 109.6(3) . . ?
C10 N1 C3 110.5(3) . . ?
C1 N2 C11 127.1(4) . . ?
C1 N2 C2 109.8(3) . . ?
C11 N2 C2 120.7(3) . . ?
N2 C1 N1 113.8(4) . . ?
N2 C1 H1 125(3) . . ?
N1 C1 H1 121(3) . . ?
N2 C2 C3 103.3(4) . . ?
N2 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
N2 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
N1 C3 C2 102.3(3) . . ?
N1 C3 C4 102.9(3) . . ?
C2 C3 C4 121.0(4) . . ?
N1 C3 H3 110.0 . . ?
C2 C3 H3 110.0 . . ?
C4 C3 H3 110.0 . . ?
C5 C4 C3 103.6(4) . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C6 C5 C10 118.9(5) . . ?
C6 C5 C4 130.8(4) . . ?
C10 C5 C4 110.2(4) . . ?
C5 C6 C7 118.9(5) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.0(5) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.2(5) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 117.1(5) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
C9 C10 C5 122.9(4) . . ?
C9 C10 N1 128.3(4) . . ?
C5 C10 N1 108.8(4) . . ?
N2 C11 C12 111.3(3) . . ?
N2 C11 C18 111.4(3) . . ?
C12 C11 C18 110.6(4) . . ?
N2 C11 H11 107.8 . . ?
C12 C11 H11 107.8 . . ?
C18 C11 H11 107.8 . . ?
C13 C12 C17 119.3(4) . . ?
C13 C12 C11 122.4(4) . . ?
C17 C12 C11 118.2(4) . . ?
C12 C13 C14 120.0(5) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.9(6) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.4(6) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.5(6) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C12 120.9(5) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N2 C1 N1 173.2(4) . . . . ?
C2 N2 C1 N1 10.7(5) . . . . ?
C10 N1 C1 N2 -144.6(4) . . . . ?
C3 N1 C1 N2 -5.0(5) . . . . ?
C1 N2 C2 C3 -11.4(5) . . . . ?
C11 N2 C2 C3 -175.2(4) . . . . ?
C1 N1 C3 C2 -2.5(5) . . . . ?
C10 N1 C3 C2 144.9(4) . . . . ?
C1 N1 C3 C4 -128.6(4) . . . . ?
C10 N1 C3 C4 18.8(4) . . . . ?
N2 C2 C3 N1 7.8(4) . . . . ?
N2 C2 C3 C4 121.2(4) . . . . ?
N1 C3 C4 C5 -19.0(4) . . . . ?
C2 C3 C4 C5 -132.0(4) . . . . ?
C3 C4 C5 C6 -170.2(5) . . . . ?
C3 C4 C5 C10 14.2(5) . . . . ?
C10 C5 C6 C7 1.1(8) . . . . ?
C4 C5 C6 C7 -174.1(5) . . . . ?
C5 C6 C7 C8 -0.7(9) . . . . ?
C6 C7 C8 C9 0.3(9) . . . . ?
C7 C8 C9 C10 -0.3(8) . . . . ?
C8 C9 C10 C5 0.8(7) . . . . ?
C8 C9 C10 N1 178.1(5) . . . . ?
C6 C5 C10 C9 -1.2(7) . . . . ?
C4 C5 C10 C9 175.0(4) . . . . ?
C6 C5 C10 N1 -179.0(4) . . . . ?
C4 C5 C10 N1 -2.8(5) . . . . ?
C1 N1 C10 C9 -48.8(7) . . . . ?
C3 N1 C10 C9 171.9(5) . . . . ?
C1 N1 C10 C5 128.8(4) . . . . ?
C3 N1 C10 C5 -10.5(5) . . . . ?
C1 N2 C11 C12 130.7(4) . . . . ?
C2 N2 C11 C12 -68.5(5) . . . . ?
C1 N2 C11 C18 6.8(6) . . . . ?
C2 N2 C11 C18 167.6(4) . . . . ?
N2 C11 C12 C13 -33.1(6) . . . . ?
C18 C11 C12 C13 91.3(5) . . . . ?
N2 C11 C12 C17 151.5(4) . . . . ?
C18 C11 C12 C17 -84.1(5) . . . . ?
C17 C12 C13 C14 0.1(7) . . . . ?
C11 C12 C13 C14 -175.3(4) . . . . ?
C12 C13 C14 C15 1.2(8) . . . . ?
C13 C14 C15 C16 -1.7(9) . . . . ?
C14 C15 C16 C17 0.8(9) . . . . ?
C15 C16 C17 C12 0.6(9) . . . . ?
C13 C12 C17 C16 -1.1(8) . . . . ?
C11 C12 C17 C16 174.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 I1 0.93(5) 2.89(5) 3.778(4) 159(4) .

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.108

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 1017397'
