# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vbchem143_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1474939'
_audit_update_record             
;
2016-05-01 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 I N2'
_chemical_formula_weight         334.15

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                   9.7777(6)
_cell_length_b                   14.7275(9)
_cell_length_c                   18.3746(13)
_cell_angle_alpha                94.956(3)
_cell_angle_beta                 98.625(3)
_cell_angle_gamma                90.324(3)
_cell_volume                     2605.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    10156
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.20

_exptl_crystal_description       dagger
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.437
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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 sacn'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            85150
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.125
_diffrn_reflns_theta_max         28.572
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             13149
_reflns_number_gt                8685
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²] 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_number_reflns         13149
_refine_ls_number_parameters     617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2551
_refine_ls_wR_factor_gt          0.2179
_refine_ls_goodness_of_fit_ref   1.650
_refine_ls_restrained_S_all      1.650
_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 0.41174(5) 0.44581(4) 0.59861(3) 0.05587(18) Uani 1 1 d . . . . .
I3 I -0.14526(5) 0.05164(4) 0.39432(3) 0.05763(18) Uani 1 1 d . . . . .
I4 I 0.54186(5) 0.19709(4) 0.24312(3) 0.05787(19) Uani 1 1 d . . . . .
I2 I 1.18553(6) 0.29908(4) 0.75371(3) 0.06158(19) Uani 1 1 d . . . . .
N3 N 0.8763(6) 0.2183(4) 0.8709(3) 0.0507(14) Uani 1 1 d . . . . .
N5 N 0.0468(6) 0.2836(4) 0.3332(3) 0.0395(12) Uani 1 1 d . . . . .
N1 N 0.6393(6) 0.2160(4) 0.6598(3) 0.0433(13) Uani 1 1 d . . . . .
N7 N 0.1699(6) 0.2786(4) 0.1237(3) 0.0531(15) Uani 1 1 d . . . . .
N2 N 0.4459(6) 0.2838(4) 0.6868(3) 0.0465(14) Uani 1 1 d . . . . .
N6 N -0.1608(6) 0.2127(4) 0.3048(3) 0.0468(14) Uani 1 1 d . . . . .
C2 C 0.7158(7) 0.3236(5) 0.5714(4) 0.0471(16) Uani 1 1 d . . . . .
N4 N 0.9053(7) 0.3355(5) 0.8026(4) 0.0631(18) Uani 1 1 d . . . . .
N8 N 0.2334(7) 0.1621(4) 0.1921(4) 0.0575(16) Uani 1 1 d . . . . .
C8 C 0.6226(7) 0.2927(5) 0.6203(4) 0.0432(15) Uani 1 1 d . . . . .
C22 C 1.1090(7) 0.1408(5) 0.8703(4) 0.0443(15) Uani 1 1 d . . . . .
C30 C 0.0536(6) 0.2070(4) 0.3733(4) 0.0389(14) Uani 1 1 d . . . . .
C1 C 0.5060(6) 0.3302(4) 0.6392(4) 0.0401(14) Uani 1 1 d . . . . .
C31 C 0.1740(7) 0.1755(4) 0.4232(4) 0.0461(16) Uani 1 1 d . . . . .
C32 C 0.1695(8) 0.1809(5) 0.4970(4) 0.0559(19) Uani 1 1 d . . . . .
H32 H 0.0939 0.2060 0.5161 0.067 Uiso 1 1 calc R U . . .
C21 C 1.0029(7) 0.2066(5) 0.8481(4) 0.0501(18) Uani 1 1 d . . . . .
C15 C 1.0160(8) 0.2789(5) 0.8067(4) 0.0515(17) Uani 1 1 d . . . . .
C29 C -0.0737(6) 0.1679(4) 0.3534(4) 0.0390(14) Uani 1 1 d . . . . .
C9 C 0.6715(8) 0.3169(5) 0.4944(4) 0.0521(18) Uani 1 1 d . . . . .
H9 H 0.5865 0.2897 0.4746 0.062 Uiso 1 1 calc R U . . .
C51 C 0.1298(8) 0.1991(6) 0.1526(4) 0.0560(19) Uani 1 1 d . . . . .
C16 C 0.8207(8) 0.2982(5) 0.8417(4) 0.0551(19) Uani 1 1 d . . . . .
C3 C 0.5280(8) 0.2125(5) 0.6987(4) 0.0489(17) Uani 1 1 d . . . . .
C43 C 0.3421(7) 0.2177(5) 0.1903(4) 0.0505(17) Uani 1 1 d . . . . .
C37 C -0.0852(7) 0.2852(5) 0.2936(4) 0.0486(17) Uani 1 1 d . . . . .
C13 C 0.8427(8) 0.3642(5) 0.5999(5) 0.059(2) Uani 1 1 d . . . . .
H13 H 0.8716 0.3703 0.6507 0.070 Uiso 1 1 calc R U . . .
C36 C 0.2861(7) 0.1371(5) 0.3945(5) 0.0534(18) Uani 1 1 d . . . . .
H36 H 0.2901 0.1329 0.3440 0.064 Uiso 1 1 calc R U . . .
C41 C 0.1419(8) 0.3549(5) 0.3312(4) 0.0550(19) Uani 1 1 d . . . . .
C35 C 0.3917(8) 0.1051(5) 0.4441(5) 0.066(3) Uani 1 1 d . . . . .
H35 H 0.4661 0.0778 0.4254 0.079 Uiso 1 1 calc R U . . .
C45 C 0.4086(7) 0.3610(5) 0.1338(4) 0.0472(16) Uani 1 1 d . . . . .
C17 C 0.6904(10) 0.3280(8) 0.8549(6) 0.081(3) Uani 1 1 d . . . . .
H17 H 0.6539 0.3812 0.8366 0.097 Uiso 1 1 calc R U . . .
C46 C 0.4680(10) 0.3564(6) 0.0698(5) 0.068(2) Uani 1 1 d . . . . .
H46 H 0.4392 0.3110 0.0322 0.081 Uiso 1 1 calc R U . . .
C27 C 1.1420(9) 0.0727(5) 0.8205(5) 0.059(2) Uani 1 1 d . . . . .
H27 H 1.0913 0.0653 0.7733 0.070 Uiso 1 1 calc R U . . .
C40 C 0.0974(11) 0.4223(6) 0.2881(5) 0.069(3) Uani 1 1 d . . . . .
H40 H 0.1580 0.4707 0.2864 0.083 Uiso 1 1 calc R U . . .
C23 C 1.1875(10) 0.1510(6) 0.9395(5) 0.068(2) Uani 1 1 d . . . . .
H23 H 1.1657 0.1964 0.9741 0.082 Uiso 1 1 calc R U . . .
C44 C 0.3122(6) 0.2905(5) 0.1486(4) 0.0453(16) Uani 1 1 d . . . . .
C4 C 0.5083(10) 0.1406(6) 0.7402(5) 0.064(2) Uani 1 1 d . . . . .
H4 H 0.4319 0.1375 0.7647 0.077 Uiso 1 1 calc R U . . .
C7 C 0.7341(8) 0.1466(5) 0.6615(4) 0.0554(19) Uani 1 1 d . . . . .
C55 C 0.0784(9) 0.3290(7) 0.0817(5) 0.071(3) Uani 1 1 d . . . . .
C49 C 0.5531(9) 0.4918(5) 0.1776(5) 0.061(2) Uani 1 1 d . . . . .
H49 H 0.5823 0.5383 0.2142 0.073 Uiso 1 1 calc R U . . .
C33 C 0.2806(11) 0.1482(6) 0.5434(5) 0.075(3) Uani 1 1 d . . . . .
H33 H 0.2796 0.1511 0.5941 0.090 Uiso 1 1 calc R U . . .
C48 C 0.6083(9) 0.4858(6) 0.1140(5) 0.069(2) Uani 1 1 d . . . . .
H48 H 0.6738 0.5288 0.1067 0.083 Uiso 1 1 calc R U . . .
C20 C 0.7980(9) 0.1632(7) 0.9077(5) 0.063(2) Uani 1 1 d . . . . .
C10 C 0.7555(11) 0.3510(6) 0.4489(5) 0.071(3) Uani 1 1 d . . . . .
H10 H 0.7260 0.3495 0.3982 0.086 Uiso 1 1 calc R U . . .
C12 C 0.9249(9) 0.3952(6) 0.5539(6) 0.067(2) Uani 1 1 d . . . . .
H12 H 1.0104 0.4221 0.5732 0.080 Uiso 1 1 calc R U . . .
C50 C 0.4537(9) 0.4290(5) 0.1885(5) 0.059(2) Uani 1 1 d . . . . .
H50 H 0.4174 0.4328 0.2326 0.071 Uiso 1 1 calc R U . . .
C38 C -0.1276(9) 0.3559(6) 0.2497(5) 0.065(2) Uani 1 1 d . . . . .
H38 H -0.2168 0.3569 0.2238 0.078 Uiso 1 1 calc R U . . .
C26 C 1.2511(12) 0.0147(6) 0.8400(8) 0.086(3) Uani 1 1 d . . . . .
H26 H 1.2731 -0.0321 0.8066 0.104 Uiso 1 1 calc R U . . .
C6 C 0.7183(11) 0.0792(6) 0.7044(5) 0.073(3) Uani 1 1 d . . . . .
H6 H 0.7843 0.0339 0.7082 0.088 Uiso 1 1 calc R U . . .
C11 C 0.8825(13) 0.3870(7) 0.4789(8) 0.095(4) Uani 1 1 d . . . . .
H11 H 0.9416 0.4065 0.4479 0.114 Uiso 1 1 calc R U . . .
C52 C -0.0125(9) 0.1709(7) 0.1358(5) 0.077(3) Uani 1 1 d . . . . .
H52 H -0.0430 0.1183 0.1535 0.092 Uiso 1 1 calc R U . . .
C54 C -0.0577(9) 0.2999(9) 0.0659(6) 0.091(4) Uani 1 1 d . . . . .
H54 H -0.1214 0.3326 0.0361 0.110 Uiso 1 1 calc R U . . .
C34 C 0.3937(11) 0.1108(7) 0.5136(7) 0.096(4) Uani 1 1 d . . . . .
H34 H 0.4694 0.0903 0.5444 0.115 Uiso 1 1 calc R U . . .
C14 C 0.8462(10) 0.1475(6) 0.6149(6) 0.085(3) Uani 1 1 d . . . . .
H14A H 0.9113 0.1959 0.6341 0.128 Uiso 1 1 calc R U . . .
H14B H 0.8070 0.1570 0.5651 0.128 Uiso 1 1 calc R U . . .
H14C H 0.8925 0.0902 0.6154 0.128 Uiso 1 1 calc R U . . .
C42 C 0.2790(9) 0.3546(6) 0.3775(5) 0.073(3) Uani 1 1 d . . . . .
H42A H 0.3321 0.3054 0.3592 0.110 Uiso 1 1 calc R U . . .
H42B H 0.2676 0.3468 0.4276 0.110 Uiso 1 1 calc R U . . .
H42C H 0.3266 0.4114 0.3758 0.110 Uiso 1 1 calc R U . . .
C47 C 0.5685(12) 0.4177(8) 0.0613(5) 0.084(3) Uani 1 1 d . . . . .
H47 H 0.6097 0.4124 0.0187 0.101 Uiso 1 1 calc R U . . .
C19 C 0.6698(10) 0.1969(9) 0.9198(6) 0.089(4) Uani 1 1 d . . . . .
H19 H 0.6157 0.1635 0.9460 0.107 Uiso 1 1 calc R U . . .
C5 C 0.6064(13) 0.0743(6) 0.7437(5) 0.084(3) Uani 1 1 d . . . . .
H5 H 0.5987 0.0258 0.7722 0.101 Uiso 1 1 calc R U . . .
C18 C 0.6196(10) 0.2778(8) 0.8947(5) 0.083(3) Uani 1 1 d . . . . .
H18 H 0.5344 0.2979 0.9056 0.099 Uiso 1 1 calc R U . . .
C28 C 0.8515(11) 0.0756(7) 0.9291(6) 0.095(4) Uani 1 1 d . . . . .
H28A H 0.9315 0.0855 0.9663 0.143 Uiso 1 1 calc R U . . .
H28B H 0.8766 0.0406 0.8867 0.143 Uiso 1 1 calc R U . . .
H28C H 0.7816 0.0429 0.9484 0.143 Uiso 1 1 calc R U . . .
C25 C 1.3245(11) 0.0283(9) 0.9091(9) 0.107(5) Uani 1 1 d . . . . .
H25 H 1.3966 -0.0105 0.9229 0.128 Uiso 1 1 calc R U . . .
C39 C -0.0334(12) 0.4234(6) 0.2464(6) 0.080(3) Uani 1 1 d . . . . .
H39 H -0.0567 0.4701 0.2161 0.096 Uiso 1 1 calc R U . . .
C24 C 1.2959(10) 0.0964(8) 0.9581(7) 0.087(3) Uani 1 1 d . . . . .
H24 H 1.3501 0.1057 1.0043 0.104 Uiso 1 1 calc R U . . .
C53 C -0.1006(10) 0.2207(8) 0.0946(5) 0.084(3) Uani 1 1 d . . . . .
H53 H -0.1934 0.2029 0.0844 0.101 Uiso 1 1 calc R U . . .
C56 C 0.1232(13) 0.4156(8) 0.0572(8) 0.123(5) Uani 1 1 d . . . . .
H56A H 0.0573 0.4325 0.0167 0.184 Uiso 1 1 calc R U . . .
H56B H 0.2122 0.4083 0.0415 0.184 Uiso 1 1 calc R U . . .
H56C H 0.1294 0.4625 0.0973 0.184 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 C1 2.082(7) . ?
I3 C29 2.086(7) . ?
I4 C43 2.083(7) . ?
I2 C15 2.077(7) . ?
N3 C21 1.372(9) . ?
N3 C20 1.394(10) . ?
N3 C16 1.414(10) . ?
N5 C37 1.385(9) . ?
N5 C30 1.397(8) . ?
N5 C41 1.405(9) . ?
N1 C7 1.382(9) . ?
N1 C3 1.391(10) . ?
N1 C8 1.392(9) . ?
N7 C55 1.358(10) . ?
N7 C44 1.403(8) . ?
N7 C51 1.404(11) . ?
N2 C3 1.338(9) . ?
N2 C1 1.354(8) . ?
N6 C37 1.344(9) . ?
N6 C29 1.356(8) . ?
C2 C13 1.384(10) . ?
C2 C9 1.411(11) . ?
C2 C8 1.467(9) . ?
N4 C16 1.320(10) . ?
N4 C15 1.367(10) . ?
N8 C51 1.305(10) . ?
N8 C43 1.343(9) . ?
C8 C1 1.349(9) . ?
C22 C27 1.372(10) . ?
C22 C23 1.379(11) . ?
C22 C21 1.461(10) . ?
C30 C29 1.354(9) . ?
C30 C31 1.483(9) . ?
C31 C32 1.358(11) . ?
C31 C36 1.389(10) . ?
C32 C33 1.392(12) . ?
C32 H32 0.9300 . ?
C21 C15 1.377(11) . ?
C9 C10 1.379(11) . ?
C9 H9 0.9300 . ?
C51 C52 1.431(11) . ?
C16 C17 1.399(11) . ?
C3 C4 1.386(11) . ?
C43 C44 1.379(10) . ?
C37 C38 1.398(10) . ?
C13 C12 1.354(11) . ?
C13 H13 0.9300 . ?
C36 C35 1.385(10) . ?
C36 H36 0.9300 . ?
C41 C40 1.357(12) . ?
C41 C42 1.477(12) . ?
C35 C34 1.270(15) . ?
C35 H35 0.9300 . ?
C45 C50 1.377(11) . ?
C45 C46 1.384(11) . ?
C45 C44 1.468(10) . ?
C17 C18 1.343(15) . ?
C17 H17 0.9300 . ?
C46 C47 1.366(13) . ?
C46 H46 0.9300 . ?
C27 C26 1.395(12) . ?
C27 H27 0.9300 . ?
C40 C39 1.390(14) . ?
C40 H40 0.9300 . ?
C23 C24 1.355(13) . ?
C23 H23 0.9300 . ?
C4 C5 1.372(14) . ?
C4 H4 0.9300 . ?
C7 C6 1.342(13) . ?
C7 C14 1.489(12) . ?
C55 C54 1.376(13) . ?
C55 C56 1.475(15) . ?
C49 C48 1.356(12) . ?
C49 C50 1.386(11) . ?
C49 H49 0.9300 . ?
C33 C34 1.401(15) . ?
C33 H33 0.9300 . ?
C48 C47 1.345(13) . ?
C48 H48 0.9300 . ?
C20 C19 1.392(13) . ?
C20 C28 1.459(14) . ?
C10 C11 1.366(16) . ?
C10 H10 0.9300 . ?
C12 C11 1.373(16) . ?
C12 H12 0.9300 . ?
C50 H50 0.9300 . ?
C38 C39 1.362(13) . ?
C38 H38 0.9300 . ?
C26 C25 1.360(17) . ?
C26 H26 0.9300 . ?
C6 C5 1.404(15) . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C52 C53 1.327(14) . ?
C52 H52 0.9300 . ?
C54 C53 1.407(16) . ?
C54 H54 0.9300 . ?
C34 H34 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C47 H47 0.9300 . ?
C19 C18 1.381(16) . ?
C19 H19 0.9300 . ?
C5 H5 0.9300 . ?
C18 H18 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C25 C24 1.348(17) . ?
C25 H25 0.9300 . ?
C39 H39 0.9300 . ?
C24 H24 0.9300 . ?
C53 H53 0.9300 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 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
C21 N3 C20 132.0(7) . . ?
C21 N3 C16 106.7(6) . . ?
C20 N3 C16 120.9(7) . . ?
C37 N5 C30 107.5(6) . . ?
C37 N5 C41 120.3(6) . . ?
C30 N5 C41 132.1(6) . . ?
C7 N1 C3 120.3(6) . . ?
C7 N1 C8 132.5(7) . . ?
C3 N1 C8 107.0(6) . . ?
C55 N7 C44 131.7(8) . . ?
C55 N7 C51 122.3(7) . . ?
C44 N7 C51 106.0(6) . . ?
C3 N2 C1 104.2(6) . . ?
C37 N6 C29 103.6(6) . . ?
C13 C2 C9 119.4(7) . . ?
C13 C2 C8 121.1(7) . . ?
C9 C2 C8 119.4(7) . . ?
C16 N4 C15 104.0(7) . . ?
C51 N8 C43 104.6(7) . . ?
C1 C8 N1 103.9(6) . . ?
C1 C8 C2 129.9(7) . . ?
N1 C8 C2 126.2(6) . . ?
C27 C22 C23 118.3(7) . . ?
C27 C22 C21 120.7(7) . . ?
C23 C22 C21 120.7(7) . . ?
C29 C30 N5 103.2(6) . . ?
C29 C30 C31 129.1(6) . . ?
N5 C30 C31 127.6(6) . . ?
C8 C1 N2 114.3(6) . . ?
C8 C1 I1 126.1(5) . . ?
N2 C1 I1 119.6(5) . . ?
C32 C31 C36 120.8(7) . . ?
C32 C31 C30 118.7(6) . . ?
C36 C31 C30 120.4(7) . . ?
C31 C32 C33 118.6(8) . . ?
C31 C32 H32 120.7 . . ?
C33 C32 H32 120.7 . . ?
C15 C21 N3 104.2(6) . . ?
C15 C21 C22 126.8(6) . . ?
N3 C21 C22 128.5(7) . . ?
N4 C15 C21 113.5(7) . . ?
N4 C15 I2 123.0(6) . . ?
C21 C15 I2 123.5(5) . . ?
N6 C29 C30 114.9(6) . . ?
N6 C29 I3 119.3(5) . . ?
C30 C29 I3 125.8(5) . . ?
C10 C9 C2 119.4(8) . . ?
C10 C9 H9 120.3 . . ?
C2 C9 H9 120.3 . . ?
N8 C51 N7 112.2(7) . . ?
N8 C51 C52 130.0(9) . . ?
N7 C51 C52 117.8(8) . . ?
N4 C16 C17 128.0(9) . . ?
N4 C16 N3 111.6(6) . . ?
C17 C16 N3 120.5(9) . . ?
N2 C3 C4 127.5(8) . . ?
N2 C3 N1 110.6(6) . . ?
C4 C3 N1 121.8(8) . . ?
N8 C43 C44 114.4(7) . . ?
N8 C43 I4 124.2(6) . . ?
C44 C43 I4 121.4(5) . . ?
N6 C37 N5 110.9(6) . . ?
N6 C37 C38 127.3(7) . . ?
N5 C37 C38 121.8(7) . . ?
C12 C13 C2 120.1(9) . . ?
C12 C13 H13 119.9 . . ?
C2 C13 H13 119.9 . . ?
C35 C36 C31 117.1(8) . . ?
C35 C36 H36 121.4 . . ?
C31 C36 H36 121.4 . . ?
C40 C41 N5 116.4(8) . . ?
C40 C41 C42 124.3(8) . . ?
N5 C41 C42 119.3(7) . . ?
C34 C35 C36 124.3(9) . . ?
C34 C35 H35 117.8 . . ?
C36 C35 H35 117.8 . . ?
C50 C45 C46 118.1(7) . . ?
C50 C45 C44 119.1(7) . . ?
C46 C45 C44 122.4(7) . . ?
C18 C17 C16 118.1(10) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C47 C46 C45 120.8(9) . . ?
C47 C46 H46 119.6 . . ?
C45 C46 H46 119.6 . . ?
C22 C27 C26 120.6(9) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C41 C40 C39 123.9(9) . . ?
C41 C40 H40 118.1 . . ?
C39 C40 H40 118.1 . . ?
C24 C23 C22 121.3(10) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C43 C44 N7 102.8(6) . . ?
C43 C44 C45 127.5(6) . . ?
N7 C44 C45 129.7(7) . . ?
C5 C4 C3 117.0(9) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?
C6 C7 N1 117.8(8) . . ?
C6 C7 C14 122.5(8) . . ?
N1 C7 C14 119.7(7) . . ?
N7 C55 C54 118.7(10) . . ?
N7 C55 C56 120.3(8) . . ?
C54 C55 C56 120.9(9) . . ?
C48 C49 C50 120.5(8) . . ?
C48 C49 H49 119.8 . . ?
C50 C49 H49 119.8 . . ?
C32 C33 C34 119.9(9) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C47 C48 C49 120.1(9) . . ?
C47 C48 H48 119.9 . . ?
C49 C48 H48 119.9 . . ?
C19 C20 N3 115.8(10) . . ?
C19 C20 C28 124.7(9) . . ?
N3 C20 C28 119.6(7) . . ?
C11 C10 C9 119.2(9) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C13 C12 C11 120.3(8) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C45 C50 C49 119.9(8) . . ?
C45 C50 H50 120.1 . . ?
C49 C50 H50 120.1 . . ?
C39 C38 C37 117.6(8) . . ?
C39 C38 H38 121.2 . . ?
C37 C38 H38 121.2 . . ?
C25 C26 C27 118.2(10) . . ?
C25 C26 H26 120.9 . . ?
C27 C26 H26 120.9 . . ?
C7 C6 C5 122.7(9) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C12 C11 C10 121.4(8) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C53 C52 C51 119.2(10) . . ?
C53 C52 H52 120.4 . . ?
C51 C52 H52 120.4 . . ?
C55 C54 C53 120.1(10) . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C35 C34 C33 119.2(8) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C48 C47 C46 120.5(9) . . ?
C48 C47 H47 119.8 . . ?
C46 C47 H47 119.8 . . ?
C18 C19 C20 122.7(10) . . ?
C18 C19 H19 118.6 . . ?
C20 C19 H19 118.6 . . ?
C4 C5 C6 120.3(8) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C17 C18 C19 121.8(9) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C20 C28 H28A 109.5 . . ?
C20 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C20 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C25 C26 122.0(10) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C38 C39 C40 120.1(9) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 H39 120.0 . . ?
C25 C24 C23 119.5(11) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C52 C53 C54 121.9(9) . . ?
C52 C53 H53 119.1 . . ?
C54 C53 H53 119.1 . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?

_refine_diff_density_max         3.569
_refine_diff_density_min         -1.342
_refine_diff_density_rms         0.212

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vbchem146_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1474941'
_audit_update_record             
;
2016-05-01 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 I N2'
_chemical_formula_weight         334.15

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                   8.2657(4)
_cell_length_b                   14.1996(6)
_cell_length_c                   21.2896(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2498.75(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7256
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.20

_exptl_crystal_description       prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    2.541
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5488
_exptl_absorpt_correction_T_max  0.7517
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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 scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            83026
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.724
_diffrn_reflns_theta_max         28.786
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6479
_reflns_number_gt                6047
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²] 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 2559 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6479
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
I2 I 0.31576(6) 0.59547(3) 0.35880(2) 0.03561(14) Uani 1 1 d . . . . .
I1 I 0.36719(6) 1.08823(3) 0.32297(2) 0.03702(14) Uani 1 1 d . . . . .
N3 N 0.4333(7) 0.4273(4) 0.4339(2) 0.0287(11) Uani 1 1 d . . . . .
N2 N 0.2363(7) 0.7961(4) 0.3099(2) 0.0280(10) Uani 1 1 d . . . . .
N1 N 0.2651(6) 0.9193(4) 0.2456(2) 0.0280(10) Uani 1 1 d . . . . .
N4 N 0.4123(7) 0.2981(4) 0.3728(2) 0.0315(11) Uani 1 1 d . . . . .
C21 C 0.3612(8) 0.4559(4) 0.3788(3) 0.0289(12) Uani 1 1 d . . . . .
C23 C 0.2913(7) 0.3687(4) 0.2765(3) 0.0273(11) Uani 1 1 d . . . . .
C4 C 0.1634(9) 0.7773(5) 0.1971(3) 0.0345(14) Uani 1 1 d . . . . .
C18 C 0.5414(9) 0.2834(5) 0.4779(3) 0.0336(13) Uani 1 1 d . . . . .
C15 C 0.4788(10) 0.4781(5) 0.4855(3) 0.0394(15) Uani 1 1 d . . . . .
H15 H 0.4562 0.5421 0.4882 0.047 Uiso 1 1 calc R U . . .
C20 C 0.4624(8) 0.3309(4) 0.4282(3) 0.0279(11) Uani 1 1 d . . . . .
C6 C 0.2205(7) 0.8254(4) 0.2511(3) 0.0269(11) Uani 1 1 d . . . . .
C25 C 0.1182(9) 0.4176(6) 0.1921(4) 0.0418(16) Uani 1 1 d . . . . .
H25 H 0.0362 0.4565 0.1771 0.050 Uiso 1 1 calc R U . . .
C24 C 0.1640(8) 0.4223(5) 0.2541(3) 0.0333(13) Uani 1 1 d . . . . .
H24 H 0.1086 0.4620 0.2814 0.040 Uiso 1 1 calc R U . . .
C28 C 0.3669(9) 0.3045(5) 0.2357(3) 0.0305(12) Uani 1 1 d . . . . .
H28 H 0.4502 0.2662 0.2502 0.037 Uiso 1 1 calc R U . . .
C17 C 0.5877(11) 0.3354(6) 0.5290(4) 0.0446(18) Uani 1 1 d . . . . .
H17 H 0.6402 0.3056 0.5621 0.054 Uiso 1 1 calc R U . . .
C7 C 0.3122(8) 0.9497(4) 0.3046(3) 0.0268(11) Uani 1 1 d . . . . .
C9 C 0.3159(9) 0.8661(4) 0.4118(3) 0.0288(12) Uani 1 1 d . . . . .
C1 C 0.2579(9) 0.9688(5) 0.1896(3) 0.0351(13) Uani 1 1 d . . . . .
H1 H 0.2896 1.0315 0.1872 0.042 Uiso 1 1 calc R U . . .
C27 C 0.3161(11) 0.2988(5) 0.1733(3) 0.0424(15) Uani 1 1 d . . . . .
H27 H 0.3658 0.2563 0.1463 0.051 Uiso 1 1 calc R U . . .
C3 C 0.1581(11) 0.8262(6) 0.1417(3) 0.0453(18) Uani 1 1 d . . . . .
H3 H 0.1240 0.7957 0.1054 0.054 Uiso 1 1 calc R U . . .
C22 C 0.3483(8) 0.3753(4) 0.3419(3) 0.0299(13) Uani 1 1 d . . . . .
C14 C 0.2096(9) 0.8115(5) 0.4467(3) 0.0358(14) Uani 1 1 d . . . . .
H14 H 0.1268 0.7787 0.4268 0.043 Uiso 1 1 calc R U . . .
C2 C 0.2031(10) 0.9221(6) 0.1386(3) 0.0429(16) Uani 1 1 d . . . . .
H2 H 0.1947 0.9538 0.1005 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4570(11) 0.9085(5) 0.5065(3) 0.0469(18) Uani 1 1 d . . . . .
H11 H 0.5390 0.9417 0.5267 0.056 Uiso 1 1 calc R U . . .
C8 C 0.2923(8) 0.8725(4) 0.3435(3) 0.0285(12) Uani 1 1 d . . . . .
C12 C 0.3517(13) 0.8531(6) 0.5409(3) 0.051(2) Uani 1 1 d . . . . .
H12 H 0.3652 0.8477 0.5841 0.061 Uiso 1 1 calc R U . . .
C13 C 0.2274(13) 0.8059(5) 0.5118(3) 0.048(2) Uani 1 1 d . . . . .
H13 H 0.1552 0.7702 0.5354 0.058 Uiso 1 1 calc R U . . .
C26 C 0.1948(11) 0.3547(6) 0.1516(4) 0.0467(18) Uani 1 1 d . . . . .
H26 H 0.1630 0.3510 0.1098 0.056 Uiso 1 1 calc R U . . .
C5 C 0.1117(15) 0.6764(6) 0.2037(4) 0.056(2) Uani 1 1 d . . . . .
H5A H 0.0590 0.6564 0.1658 0.084 Uiso 1 1 calc R U . . .
H5B H 0.0380 0.6707 0.2383 0.084 Uiso 1 1 calc R U . . .
H5C H 0.2049 0.6377 0.2111 0.084 Uiso 1 1 calc R U . . .
C10 C 0.4395(11) 0.9144(5) 0.4417(3) 0.0437(16) Uani 1 1 d . . . . .
H10 H 0.5110 0.9509 0.4184 0.052 Uiso 1 1 calc R U . . .
C16 C 0.5578(11) 0.4330(5) 0.5328(3) 0.0449(18) Uani 1 1 d . . . . .
H16 H 0.5923 0.4667 0.5677 0.054 Uiso 1 1 calc R U . . .
C19 C 0.5741(12) 0.1783(6) 0.4733(4) 0.0478(19) Uani 1 1 d . . . . .
H19A H 0.6353 0.1582 0.5092 0.072 Uiso 1 1 calc R U . . .
H19B H 0.6344 0.1654 0.4357 0.072 Uiso 1 1 calc R U . . .
H19C H 0.4732 0.1448 0.4720 0.072 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
I2 C21 2.061(6) . ?
I1 C7 2.056(6) . ?
N3 C15 1.367(8) . ?
N3 C21 1.377(8) . ?
N3 C20 1.396(7) . ?
N2 C6 1.324(8) . ?
N2 C8 1.381(8) . ?
N1 C7 1.383(8) . ?
N1 C1 1.386(8) . ?
N1 C6 1.389(8) . ?
N4 C20 1.333(8) . ?
N4 C22 1.384(8) . ?
C21 C22 1.391(8) . ?
C23 C24 1.383(9) . ?
C23 C28 1.405(9) . ?
C23 C22 1.472(9) . ?
C4 C3 1.369(10) . ?
C4 C6 1.419(9) . ?
C4 C5 1.502(11) . ?
C18 C17 1.371(10) . ?
C18 C20 1.415(9) . ?
C18 C19 1.520(10) . ?
C15 C16 1.360(11) . ?
C15 H15 0.9300 . ?
C25 C24 1.376(10) . ?
C25 C26 1.393(11) . ?
C25 H25 0.9300 . ?
C24 H24 0.9300 . ?
C28 C27 1.396(9) . ?
C28 H28 0.9300 . ?
C17 C16 1.410(12) . ?
C17 H17 0.9300 . ?
C7 C8 1.385(8) . ?
C9 C10 1.386(10) . ?
C9 C14 1.387(9) . ?
C9 C8 1.469(8) . ?
C1 C2 1.350(10) . ?
C1 H1 0.9300 . ?
C27 C26 1.360(12) . ?
C27 H27 0.9300 . ?
C3 C2 1.413(12) . ?
C3 H3 0.9300 . ?
C14 C13 1.396(10) . ?
C14 H14 0.9300 . ?
C2 H2 0.9300 . ?
C11 C12 1.383(13) . ?
C11 C10 1.389(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(14) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C26 H26 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C15 N3 C21 130.4(6) . . ?
C15 N3 C20 122.7(6) . . ?
C21 N3 C20 106.9(5) . . ?
C6 N2 C8 106.0(5) . . ?
C7 N1 C1 129.4(5) . . ?
C7 N1 C6 107.3(5) . . ?
C1 N1 C6 123.2(6) . . ?
C20 N4 C22 105.2(5) . . ?
N3 C21 C22 105.7(5) . . ?
N3 C21 I2 122.5(4) . . ?
C22 C21 I2 131.3(5) . . ?
C24 C23 C28 118.8(6) . . ?
C24 C23 C22 122.3(6) . . ?
C28 C23 C22 118.9(6) . . ?
C3 C4 C6 117.7(6) . . ?
C3 C4 C5 123.7(7) . . ?
C6 C4 C5 118.6(6) . . ?
C17 C18 C20 117.7(6) . . ?
C17 C18 C19 122.1(7) . . ?
C20 C18 C19 120.1(6) . . ?
C16 C15 N3 118.6(7) . . ?
C16 C15 H15 120.7 . . ?
N3 C15 H15 120.7 . . ?
N4 C20 N3 111.5(5) . . ?
N4 C20 C18 129.6(6) . . ?
N3 C20 C18 118.9(6) . . ?
N2 C6 N1 110.8(5) . . ?
N2 C6 C4 130.3(6) . . ?
N1 C6 C4 118.8(6) . . ?
C24 C25 C26 119.9(7) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C24 C23 121.0(6) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C27 C28 C23 119.5(7) . . ?
C27 C28 H28 120.2 . . ?
C23 C28 H28 120.2 . . ?
C18 C17 C16 121.8(7) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
N1 C7 C8 105.3(5) . . ?
N1 C7 I1 122.3(4) . . ?
C8 C7 I1 132.0(5) . . ?
C10 C9 C14 119.8(6) . . ?
C10 C9 C8 121.5(6) . . ?
C14 C9 C8 118.7(6) . . ?
C2 C1 N1 117.2(6) . . ?
C2 C1 H1 121.4 . . ?
N1 C1 H1 121.4 . . ?
C26 C27 C28 120.7(7) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C4 C3 C2 121.5(7) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
N4 C22 C21 110.7(5) . . ?
N4 C22 C23 121.4(6) . . ?
C21 C22 C23 127.6(6) . . ?
C9 C14 C13 119.8(7) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C1 C2 C3 121.5(6) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C12 C11 C10 119.6(8) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
N2 C8 C7 110.6(5) . . ?
N2 C8 C9 120.6(5) . . ?
C7 C8 C9 128.8(6) . . ?
C13 C12 C11 120.6(6) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.9(8) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C27 C26 C25 120.0(7) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C9 C10 C11 120.3(8) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C15 C16 C17 120.3(7) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.733
_refine_diff_density_min         -2.843
_refine_diff_density_rms         0.356

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vbchem076_a
_database_code_depnum_ccdc_archive 'CCDC 1477441'
_audit_update_record             
;
2016-05-01 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H9 I N2 S'
_chemical_formula_weight         376.20

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'
S S 0.1246 0.1234 '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                   10.5054(6)
_cell_length_b                   13.8935(9)
_cell_length_c                   14.8405(10)
_cell_angle_alpha                102.826(4)
_cell_angle_beta                 105.411(4)
_cell_angle_gamma                94.441(4)
_cell_volume                     2014.5(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    10601
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.50

_exptl_crystal_description       prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_F_000             1092
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.525
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5408
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            69187
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.471
_diffrn_reflns_theta_max         28.959
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10591
_reflns_number_gt                6070
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²] 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_number_reflns         10591
_refine_ls_number_parameters     514
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1859
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
I3 I 0.67670(4) 0.12436(3) 1.22447(4) 0.06557(16) Uani 1 1 d . . . . .
I2 I 0.67295(5) 0.02162(4) 0.65320(3) 0.06655(16) Uani 1 1 d . . . . .
I1 I 0.98031(5) 0.40067(4) 0.35500(4) 0.07820(19) Uani 1 1 d . . . . .
S004 S 1.24132(14) 0.65074(13) 0.18089(13) 0.0600(4) Uani 1 1 d . . . . .
S005 S 0.50758(16) 0.15349(13) 0.83441(13) 0.0598(4) Uani 1 1 d . . . . .
S006 S 0.34111(15) 0.30414(14) 0.53110(15) 0.0648(5) Uani 1 1 d . . . . .
N1 N 1.0050(4) 0.5687(3) 0.1591(3) 0.0416(10) Uani 1 1 d . . . . .
N5 N 0.4023(4) 0.1378(3) 0.9698(3) 0.0422(10) Uani 1 1 d . . . . .
N3 N 0.5637(4) 0.2481(3) 0.5183(3) 0.0447(11) Uani 1 1 d . . . . .
N6 N 0.6212(4) 0.1419(3) 1.0219(4) 0.0518(12) Uani 1 1 d . . . . .
N2 N 1.1470(4) 0.5290(4) 0.2797(4) 0.0510(12) Uani 1 1 d . . . . .
N4 N 0.4794(5) 0.1628(4) 0.6041(4) 0.0554(13) Uani 1 1 d . . . . .
C40 C 0.3246(5) 0.1192(4) 1.1109(4) 0.0401(12) Uani 1 1 d . . . . .
C16 C 0.7756(5) 0.1780(4) 0.5146(4) 0.0415(12) Uani 1 1 d . . . . .
C31 C 0.2944(5) 0.1447(4) 0.8939(4) 0.0423(12) Uani 1 1 d . . . . .
C10 C 0.7832(5) 0.4966(4) 0.1658(4) 0.0414(12) Uani 1 1 d . . . . .
C30 C 0.5429(5) 0.3156(4) 0.4615(4) 0.0422(12) Uani 1 1 d . . . . .
C1 C 0.9901(5) 0.6121(4) 0.0839(4) 0.0419(12) Uani 1 1 d . . . . .
C39 C 0.4276(5) 0.1300(4) 1.0644(4) 0.0432(12) Uani 1 1 d . . . . .
C37 C 0.5213(6) 0.1434(4) 0.9510(5) 0.0500(14) Uani 1 1 d . . . . .
C32 C 0.1636(5) 0.1452(4) 0.8917(4) 0.0455(13) Uani 1 1 d . . . . .
H32 H 0.1362 0.1415 0.9456 0.055 Uiso 1 1 calc R U . . .
C33 C 0.0733(6) 0.1511(4) 0.8073(4) 0.0483(13) Uani 1 1 d . . . . .
H33 H -0.0163 0.1513 0.8040 0.058 Uiso 1 1 calc R U . . .
C22 C 0.6514(5) 0.1825(4) 0.5409(4) 0.0457(13) Uani 1 1 d . . . . .
C38 C 0.5613(5) 0.1335(4) 1.0922(5) 0.0491(14) Uani 1 1 d . . . . .
C6 C 1.1099(6) 0.6637(4) 0.0868(5) 0.0507(14) Uani 1 1 d . . . . .
C24 C 0.4650(6) 0.2313(5) 0.5587(5) 0.0540(15) Uani 1 1 d . . . . .
C17 C 0.8703(5) 0.2599(4) 0.5450(4) 0.0454(13) Uani 1 1 d . . . . .
H17 H 0.8555 0.3190 0.5820 0.054 Uiso 1 1 calc R U . . .
C29 C 0.6225(6) 0.3471(4) 0.4111(4) 0.0494(13) Uani 1 1 d . . . . .
H29 H 0.7038 0.3242 0.4128 0.059 Uiso 1 1 calc R U . . .
C36 C 0.3361(6) 0.1521(4) 0.8133(4) 0.0484(13) Uani 1 1 d . . . . .
C45 C 0.3242(6) 0.1872(5) 1.1926(4) 0.0528(15) Uani 1 1 d . . . . .
H45 H 0.3918 0.2414 1.2195 0.063 Uiso 1 1 calc R U . . .
C41 C 0.2244(5) 0.0392(4) 1.0735(5) 0.0507(14) Uani 1 1 d . . . . .
H41 H 0.2235 -0.0096 1.0190 0.061 Uiso 1 1 calc R U . . .
C23 C 0.5960(5) 0.1319(4) 0.5921(4) 0.0479(13) Uani 1 1 d . . . . .
C21 C 0.7994(6) 0.0915(5) 0.4618(5) 0.0519(14) Uani 1 1 d . . . . .
H21 H 0.7361 0.0347 0.4422 0.062 Uiso 1 1 calc R U . . .
C18 C 0.9877(5) 0.2557(5) 0.5215(5) 0.0511(14) Uani 1 1 d . . . . .
H18 H 1.0524 0.3119 0.5430 0.061 Uiso 1 1 calc R U . . .
C2 C 0.8767(6) 0.6080(4) 0.0095(4) 0.0517(14) Uani 1 1 d . . . . .
H2 H 0.7962 0.5723 0.0061 0.062 Uiso 1 1 calc R U . . .
C9 C 0.9281(5) 0.5104(4) 0.1950(4) 0.0427(12) Uani 1 1 d . . . . .
C7 C 1.1331(5) 0.5770(4) 0.2140(4) 0.0457(13) Uani 1 1 d . . . . .
C5 C 1.1185(7) 0.7145(5) 0.0207(5) 0.0621(17) Uani 1 1 d . . . . .
H5 H 1.1992 0.7500 0.0241 0.074 Uiso 1 1 calc R U . . .
C25 C 0.4246(5) 0.3524(5) 0.4610(5) 0.0510(14) Uani 1 1 d . . . . .
C34 C 0.1153(7) 0.1569(4) 0.7270(5) 0.0553(15) Uani 1 1 d . . . . .
H34 H 0.0531 0.1598 0.6703 0.066 Uiso 1 1 calc R U . . .
C15 C 0.7069(5) 0.4044(4) 0.1339(4) 0.0463(13) Uani 1 1 d . . . . .
H15 H 0.7479 0.3473 0.1280 0.056 Uiso 1 1 calc R U . . .
C28 C 0.5787(6) 0.4141(5) 0.3579(5) 0.0574(15) Uani 1 1 d . . . . .
H28 H 0.6301 0.4353 0.3218 0.069 Uiso 1 1 calc R U . . .
C35 C 0.2455(7) 0.1584(4) 0.7304(5) 0.0565(16) Uani 1 1 d . . . . .
H35 H 0.2730 0.1637 0.6769 0.068 Uiso 1 1 calc R U . . .
C14 C 0.5702(6) 0.3959(5) 0.1105(5) 0.0593(17) Uani 1 1 d . . . . .
H14 H 0.5189 0.3331 0.0876 0.071 Uiso 1 1 calc R U . . .
C13 C 0.5095(6) 0.4797(5) 0.1209(5) 0.0614(17) Uani 1 1 d . . . . .
H13 H 0.4171 0.4740 0.1061 0.074 Uiso 1 1 calc R U . . .
C20 C 0.9173(7) 0.0880(5) 0.4374(5) 0.0602(16) Uani 1 1 d . . . . .
H20 H 0.9325 0.0290 0.4005 0.072 Uiso 1 1 calc R U . . .
C3 C 0.8853(7) 0.6575(5) -0.0588(5) 0.0626(17) Uani 1 1 d . . . . .
H3 H 0.8103 0.6542 -0.1103 0.075 Uiso 1 1 calc R U . . .
C19 C 1.0103(6) 0.1697(5) 0.4667(5) 0.0591(17) Uani 1 1 d . . . . .
H19 H 1.0893 0.1675 0.4496 0.071 Uiso 1 1 calc R U . . .
C43 C 0.1258(6) 0.1004(6) 1.1964(5) 0.0604(17) Uani 1 1 d . . . . .
H43 H 0.0568 0.0951 1.2241 0.072 Uiso 1 1 calc R U . . .
C44 C 0.2259(7) 0.1766(5) 1.2354(5) 0.0638(17) Uani 1 1 d . . . . .
H44 H 0.2283 0.2226 1.2921 0.077 Uiso 1 1 calc R U . . .
C26 C 0.3824(6) 0.4184(5) 0.4089(5) 0.0599(17) Uani 1 1 d . . . . .
H26 H 0.3018 0.4421 0.4082 0.072 Uiso 1 1 calc R U . . .
C4 C 1.0034(8) 0.7123(5) -0.0529(6) 0.070(2) Uani 1 1 d . . . . .
H4 H 1.0062 0.7482 -0.0984 0.084 Uiso 1 1 calc R U . . .
C8 C 1.0187(5) 0.4883(4) 0.2672(4) 0.0469(13) Uani 1 1 d . . . . .
C11 C 0.7195(6) 0.5799(5) 0.1734(6) 0.0645(18) Uani 1 1 d . . . . .
H11 H 0.7694 0.6430 0.1931 0.077 Uiso 1 1 calc R U . . .
C27 C 0.4603(7) 0.4498(5) 0.3573(5) 0.0593(16) Uani 1 1 d . . . . .
H27 H 0.4329 0.4956 0.3217 0.071 Uiso 1 1 calc R U . . .
C42 C 0.1261(6) 0.0320(5) 1.1171(5) 0.0615(18) Uani 1 1 d . . . . .
H42 H 0.0576 -0.0217 1.0911 0.074 Uiso 1 1 calc R U . . .
C12 C 0.5839(6) 0.5705(5) 0.1525(6) 0.073(2) Uani 1 1 d . . . . .
H12 H 0.5424 0.6273 0.1601 0.087 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
I3 C38 2.052(6) . ?
I2 C23 2.060(6) . ?
I1 C8 2.062(6) . ?
S004 C7 1.710(6) . ?
S004 C6 1.736(7) . ?
S005 C37 1.735(7) . ?
S005 C36 1.742(6) . ?
S006 C24 1.730(6) . ?
S006 C25 1.733(6) . ?
N1 C7 1.356(7) . ?
N1 C1 1.361(7) . ?
N1 C9 1.383(6) . ?
N5 C37 1.352(7) . ?
N5 C39 1.387(7) . ?
N5 C31 1.396(7) . ?
N3 C24 1.358(7) . ?
N3 C22 1.376(7) . ?
N3 C30 1.386(7) . ?
N6 C37 1.279(8) . ?
N6 C38 1.374(8) . ?
N2 C7 1.283(7) . ?
N2 C8 1.369(7) . ?
N4 C24 1.278(8) . ?
N4 C23 1.371(7) . ?
C40 C45 1.363(8) . ?
C40 C41 1.374(7) . ?
C40 C39 1.444(7) . ?
C16 C17 1.359(8) . ?
C16 C21 1.360(8) . ?
C16 C22 1.460(7) . ?
C31 C32 1.366(7) . ?
C31 C36 1.401(7) . ?
C10 C15 1.370(7) . ?
C10 C11 1.379(8) . ?
C10 C9 1.452(7) . ?
C30 C29 1.368(8) . ?
C30 C25 1.379(8) . ?
C1 C2 1.380(8) . ?
C1 C6 1.385(7) . ?
C39 C38 1.349(7) . ?
C32 C33 1.379(8) . ?
C32 H32 0.9300 . ?
C33 C34 1.391(8) . ?
C33 H33 0.9300 . ?
C22 C23 1.348(8) . ?
C6 C5 1.346(9) . ?
C17 C18 1.369(7) . ?
C17 H17 0.9300 . ?
C29 C28 1.378(8) . ?
C29 H29 0.9300 . ?
C36 C35 1.365(9) . ?
C45 C44 1.363(9) . ?
C45 H45 0.9300 . ?
C41 C42 1.366(8) . ?
C41 H41 0.9300 . ?
C21 C20 1.382(8) . ?
C21 H21 0.9300 . ?
C18 C19 1.364(9) . ?
C18 H18 0.9300 . ?
C2 C3 1.364(9) . ?
C2 H2 0.9300 . ?
C9 C8 1.341(8) . ?
C5 C4 1.391(10) . ?
C5 H5 0.9300 . ?
C25 C26 1.354(9) . ?
C34 C35 1.354(9) . ?
C34 H34 0.9300 . ?
C15 C14 1.374(8) . ?
C15 H15 0.9300 . ?
C28 C27 1.373(9) . ?
C28 H28 0.9300 . ?
C35 H35 0.9300 . ?
C14 C13 1.369(9) . ?
C14 H14 0.9300 . ?
C13 C12 1.345(9) . ?
C13 H13 0.9300 . ?
C20 C19 1.347(9) . ?
C20 H20 0.9300 . ?
C3 C4 1.375(10) . ?
C3 H3 0.9300 . ?
C19 H19 0.9300 . ?
C43 C44 1.339(10) . ?
C43 C42 1.339(10) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C26 C27 1.368(9) . ?
C26 H26 0.9300 . ?
C4 H4 0.9300 . ?
C11 C12 1.364(8) . ?
C11 H11 0.9300 . ?
C27 H27 0.9300 . ?
C42 H42 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S004 C6 89.5(3) . . ?
C37 S005 C36 89.7(3) . . ?
C24 S006 C25 89.8(3) . . ?
C7 N1 C1 114.3(4) . . ?
C7 N1 C9 106.7(5) . . ?
C1 N1 C9 138.8(5) . . ?
C37 N5 C39 106.7(5) . . ?
C37 N5 C31 114.5(5) . . ?
C39 N5 C31 138.8(4) . . ?
C24 N3 C22 105.9(5) . . ?
C24 N3 C30 114.9(5) . . ?
C22 N3 C30 138.8(5) . . ?
C37 N6 C38 102.0(5) . . ?
C7 N2 C8 102.7(5) . . ?
C24 N4 C23 102.6(5) . . ?
C45 C40 C41 118.3(5) . . ?
C45 C40 C39 121.4(5) . . ?
C41 C40 C39 120.4(5) . . ?
C17 C16 C21 119.3(5) . . ?
C17 C16 C22 120.0(5) . . ?
C21 C16 C22 120.6(5) . . ?
C32 C31 N5 128.5(5) . . ?
C32 C31 C36 120.9(5) . . ?
N5 C31 C36 110.6(5) . . ?
C15 C10 C11 118.4(5) . . ?
C15 C10 C9 122.9(5) . . ?
C11 C10 C9 118.6(5) . . ?
C29 C30 C25 120.6(5) . . ?
C29 C30 N3 128.7(5) . . ?
C25 C30 N3 110.6(5) . . ?
N1 C1 C2 128.7(5) . . ?
N1 C1 C6 111.3(5) . . ?
C2 C1 C6 120.0(5) . . ?
C38 C39 N5 102.3(5) . . ?
C38 C39 C40 134.0(6) . . ?
N5 C39 C40 123.6(5) . . ?
N6 C37 N5 114.6(6) . . ?
N6 C37 S005 132.7(4) . . ?
N5 C37 S005 112.7(5) . . ?
C31 C32 C33 118.3(5) . . ?
C31 C32 H32 120.9 . . ?
C33 C32 H32 120.9 . . ?
C32 C33 C34 120.5(6) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C23 C22 N3 103.7(5) . . ?
C23 C22 C16 132.0(5) . . ?
N3 C22 C16 124.2(5) . . ?
C39 C38 N6 114.4(6) . . ?
C39 C38 I3 126.4(5) . . ?
N6 C38 I3 119.2(4) . . ?
C5 C6 C1 121.8(6) . . ?
C5 C6 S004 126.1(5) . . ?
C1 C6 S004 112.1(4) . . ?
N4 C24 N3 114.5(5) . . ?
N4 C24 S006 133.8(5) . . ?
N3 C24 S006 111.5(5) . . ?
C16 C17 C18 120.2(6) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C30 C29 C28 117.9(6) . . ?
C30 C29 H29 121.0 . . ?
C28 C29 H29 121.0 . . ?
C35 C36 C31 120.1(5) . . ?
C35 C36 S005 127.3(5) . . ?
C31 C36 S005 112.6(5) . . ?
C44 C45 C40 120.8(6) . . ?
C44 C45 H45 119.6 . . ?
C40 C45 H45 119.6 . . ?
C42 C41 C40 119.3(6) . . ?
C42 C41 H41 120.4 . . ?
C40 C41 H41 120.4 . . ?
C22 C23 N4 113.2(5) . . ?
C22 C23 I2 126.4(4) . . ?
N4 C23 I2 120.3(4) . . ?
C16 C21 C20 120.2(6) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C19 C18 C17 120.5(6) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C3 C2 C1 118.5(6) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C8 C9 N1 102.9(4) . . ?
C8 C9 C10 132.6(5) . . ?
N1 C9 C10 123.7(5) . . ?
N2 C7 N1 113.7(5) . . ?
N2 C7 S004 133.8(4) . . ?
N1 C7 S004 112.5(4) . . ?
C6 C5 C4 118.1(6) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C26 C25 C30 121.1(6) . . ?
C26 C25 S006 125.9(5) . . ?
C30 C25 S006 113.0(5) . . ?
C35 C34 C33 120.9(6) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C10 C15 C14 120.4(6) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C27 C28 C29 121.0(6) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C34 C35 C36 119.3(6) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C13 C14 C15 120.0(6) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C12 C13 C14 119.9(6) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C19 C20 C21 120.3(6) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C2 C3 C4 121.0(7) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C20 C19 C18 119.4(6) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C44 C43 C42 119.4(6) . . ?
C44 C43 H43 120.3 . . ?
C42 C43 H43 120.3 . . ?
C43 C44 C45 120.5(7) . . ?
C43 C44 H44 119.7 . . ?
C45 C44 H44 119.7 . . ?
C25 C26 C27 118.9(6) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C3 C4 C5 120.6(6) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C9 C8 N2 114.0(5) . . ?
C9 C8 I1 126.1(4) . . ?
N2 C8 I1 119.8(4) . . ?
C12 C11 C10 120.7(6) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C26 C27 C28 120.4(6) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C43 C42 C41 121.7(6) . . ?
C43 C42 H42 119.2 . . ?
C41 C42 H42 119.2 . . ?
C13 C12 C11 120.5(6) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?

_refine_diff_density_max         1.052
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.121

_shelxl_version_number           2014/6

