# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_cd214239
_database_code_depnum_ccdc_archive 'CCDC 1026405'
_audit_update_record             
;
2014-09-26 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        HYC-Tetrazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 I N4 O'
_chemical_formula_weight         478.28

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'
O O 0.0106 0.0060 '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           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

_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'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   22.3839(14)
_cell_length_b                   36.433(2)
_cell_length_c                   10.0332(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8182.3(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6960
_cell_measurement_theta_min      4.472
_cell_measurement_theta_max      47.784

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             3776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    1.585
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6038
_exptl_absorpt_correction_T_max  0.7457
_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            24429
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.136
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             7958
_reflns_number_gt                6935
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_fraction_full    0.985

_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)+(0.0298P)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 2843 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.017(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7958
_refine_ls_number_parameters     505
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.002
_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 0.58527(2) 0.80821(2) 0.25596(5) 0.04745(11) Uani 1 1 d . . . . .
I2 I 0.35673(2) 0.43873(2) 0.46967(5) 0.05336(12) Uani 1 1 d . . . . .
N1 N 0.6391(2) 0.69568(13) 0.3340(5) 0.0371(11) Uani 1 1 d . . . . .
N2 N 0.6480(2) 0.68187(15) 0.2103(5) 0.0458(12) Uani 1 1 d . . . . .
N3 N 0.6585(2) 0.64744(15) 0.2256(5) 0.0550(14) Uani 1 1 d . . . . .
N4 N 0.6583(2) 0.63789(14) 0.3580(6) 0.0540(14) Uani 1 1 d . . . . .
N5 N 0.3928(2) 0.55040(14) 0.6039(5) 0.0476(12) Uani 1 1 d . . . . .
N6 N 0.4374(3) 0.55045(17) 0.6951(7) 0.0666(16) Uani 1 1 d . . . . .
N7 N 0.4395(2) 0.58318(17) 0.7442(8) 0.0712(17) Uani 1 1 d . . . . .
N8 N 0.3979(2) 0.60509(15) 0.6871(6) 0.0564(14) Uani 1 1 d . . . . .
O1 O 0.5562(3) 0.74235(14) 0.0517(5) 0.0792(15) Uani 1 1 d . . . . .
O2 O 0.2896(2) 0.50737(16) 0.7217(6) 0.094(2) Uani 1 1 d . . . . .
C1 C 0.4923(3) 0.6965(2) 0.3288(8) 0.062(2) Uani 1 1 d . . . . .
H1 H 0.5014 0.7137 0.3940 0.075 Uiso 1 1 calc R U . . .
C2 C 0.4553(3) 0.6671(3) 0.3589(9) 0.092(3) Uani 1 1 d . . . . .
H2 H 0.4396 0.6649 0.4443 0.111 Uiso 1 1 calc R U . . .
C3 C 0.4416(3) 0.6417(2) 0.2646(11) 0.083(2) Uani 1 1 d . . . . .
H3 H 0.4174 0.6218 0.2861 0.099 Uiso 1 1 calc R U . . .
C4 C 0.4637(3) 0.6455(2) 0.1370(9) 0.069(2) Uani 1 1 d . . . . .
H4 H 0.4539 0.6284 0.0714 0.083 Uiso 1 1 calc R U . . .
C5 C 0.5003(3) 0.67454(18) 0.1075(7) 0.0510(15) Uani 1 1 d . . . . .
H5 H 0.5151 0.6771 0.0213 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5158(2) 0.70018(17) 0.2029(6) 0.0434(14) Uani 1 1 d . . . . .
C7 C 0.5539(3) 0.73170(17) 0.1660(6) 0.0473(14) Uani 1 1 d . . . . .
C8 C 0.5903(2) 0.75080(13) 0.2720(6) 0.0365(12) Uani 1 1 d . . . . .
C9 C 0.6293(2) 0.73460(15) 0.3516(6) 0.0366(12) Uani 1 1 d . . . . .
C11 C 0.6462(2) 0.66838(16) 0.4239(6) 0.0403(14) Uani 1 1 d . . . . .
C12 C 0.6430(3) 0.67087(17) 0.5677(6) 0.0464(15) Uani 1 1 d . . . . .
C13 C 0.6850(3) 0.65165(19) 0.6437(7) 0.0582(17) Uani 1 1 d . . . . .
H13 H 0.7139 0.6375 0.6018 0.070 Uiso 1 1 calc R U . . .
C14 C 0.6834(3) 0.6537(2) 0.7814(8) 0.071(2) Uani 1 1 d . . . . .
H14 H 0.7109 0.6406 0.8317 0.086 Uiso 1 1 calc R U . . .
C15 C 0.6412(4) 0.6751(3) 0.8446(8) 0.077(2) Uani 1 1 d . . . . .
H15 H 0.6409 0.6768 0.9371 0.093 Uiso 1 1 calc R U . . .
C16 C 0.5998(3) 0.6938(2) 0.7712(9) 0.074(2) Uani 1 1 d . . . . .
H16 H 0.5712 0.7081 0.8139 0.088 Uiso 1 1 calc R U . . .
C17 C 0.6002(3) 0.6916(2) 0.6335(8) 0.0617(19) Uani 1 1 d . . . . .
H17 H 0.5714 0.7041 0.5846 0.074 Uiso 1 1 calc R U . . .
C18 C 0.6700(2) 0.75128(14) 0.4527(6) 0.0389(12) Uani 1 1 d . . . . .
C19 C 0.7299(2) 0.74189(15) 0.4516(7) 0.0448(14) Uani 1 1 d . . . . .
H19 H 0.7444 0.7255 0.3884 0.054 Uiso 1 1 calc R U . . .
C20 C 0.7679(3) 0.75703(18) 0.5451(7) 0.0562(17) Uani 1 1 d . . . . .
H20 H 0.8083 0.7512 0.5439 0.067 Uiso 1 1 calc R U . . .
C21 C 0.7460(3) 0.78082(19) 0.6401(7) 0.0626(18) Uani 1 1 d . . . . .
H21 H 0.7717 0.7909 0.7030 0.075 Uiso 1 1 calc R U . . .
C22 C 0.6866(3) 0.7896(2) 0.6424(7) 0.0631(18) Uani 1 1 d . . . . .
H22 H 0.6718 0.8055 0.7071 0.076 Uiso 1 1 calc R U . . .
C23 C 0.6485(3) 0.77476(18) 0.5474(7) 0.0504(15) Uani 1 1 d . . . . .
H23 H 0.6082 0.7808 0.5482 0.061 Uiso 1 1 calc R U . . .
C24 C 0.3175(3) 0.4552(2) 0.9175(8) 0.069(2) Uani 1 1 d . . . . .
H24 H 0.2794 0.4653 0.9216 0.082 Uiso 1 1 calc R U . . .
C25 C 0.3366(4) 0.4319(3) 1.0164(9) 0.082(3) Uani 1 1 d . . . . .
H25 H 0.3117 0.4268 1.0882 0.099 Uiso 1 1 calc R U . . .
C26 C 0.3918(3) 0.4163(2) 1.0101(8) 0.077(2) Uani 1 1 d . . . . .
H26 H 0.4040 0.3999 1.0760 0.092 Uiso 1 1 calc R U . . .
C27 C 0.4291(3) 0.4245(2) 0.9078(8) 0.072(2) Uani 1 1 d . . . . .
H27 H 0.4671 0.4142 0.9053 0.086 Uiso 1 1 calc R U . . .
C28 C 0.4112(3) 0.4480(2) 0.8073(7) 0.0583(18) Uani 1 1 d . . . . .
H28 H 0.4369 0.4532 0.7370 0.070 Uiso 1 1 calc R U . . .
C29 C 0.3549(3) 0.46362(18) 0.8115(7) 0.0524(15) Uani 1 1 d . . . . .
C30 C 0.3328(3) 0.48802(18) 0.7070(7) 0.0552(17) Uani 1 1 d . . . . .
C31 C 0.3622(2) 0.48917(15) 0.5714(6) 0.0443(14) Uani 1 1 d . . . . .
C32 C 0.3843(3) 0.51934(15) 0.5168(6) 0.0455(15) Uani 1 1 d . . . . .
C34 C 0.3685(2) 0.58443(16) 0.6004(6) 0.0434(14) Uani 1 1 d . . . . .
C35 C 0.3177(2) 0.59672(15) 0.5217(6) 0.0452(14) Uani 1 1 d . . . . .
C36 C 0.3112(3) 0.63369(16) 0.4944(7) 0.0537(16) Uani 1 1 d . . . . .
H36 H 0.3400 0.6502 0.5235 0.064 Uiso 1 1 calc R U . . .
C37 C 0.2626(3) 0.64609(19) 0.4247(7) 0.0656(19) Uani 1 1 d . . . . .
H37 H 0.2586 0.6710 0.4067 0.079 Uiso 1 1 calc R U . . .
C38 C 0.2200(4) 0.6219(2) 0.3814(9) 0.085(3) Uani 1 1 d . . . . .
H38 H 0.1873 0.6304 0.3332 0.102 Uiso 1 1 calc R U . . .
C39 C 0.2255(4) 0.5858(2) 0.4088(11) 0.101(3) Uani 1 1 d . . . . .
H39 H 0.1960 0.5696 0.3803 0.121 Uiso 1 1 calc R U . . .
C40 C 0.2738(3) 0.57261(18) 0.4779(11) 0.078(2) Uani 1 1 d . . . . .
H40 H 0.2771 0.5476 0.4954 0.093 Uiso 1 1 calc R U . . .
C41 C 0.4054(3) 0.52592(17) 0.3794(8) 0.0510(17) Uani 1 1 d . . . . .
C42 C 0.4612(3) 0.5407(2) 0.3583(9) 0.069(2) Uani 1 1 d . . . . .
H42 H 0.4851 0.5469 0.4306 0.082 Uiso 1 1 calc R U . . .
C43 C 0.4820(4) 0.5463(3) 0.2294(11) 0.093(3) Uani 1 1 d . . . . .
H43 H 0.5204 0.5553 0.2156 0.112 Uiso 1 1 calc R U . . .
C44 C 0.4463(6) 0.5388(3) 0.1239(12) 0.107(4) Uani 1 1 d . . . . .
H44 H 0.4599 0.5430 0.0376 0.128 Uiso 1 1 calc R U . . .
C45 C 0.3908(6) 0.5250(3) 0.1443(10) 0.099(3) Uani 1 1 d . . . . .
H45 H 0.3663 0.5201 0.0716 0.118 Uiso 1 1 calc R U . . .
C46 C 0.3703(3) 0.5181(2) 0.2717(9) 0.072(2) Uani 1 1 d . . . . .
H46 H 0.3325 0.5080 0.2842 0.086 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 C8 2.101(5) . ?
I2 C31 2.105(6) . ?
N1 C11 1.352(7) . ?
N1 N2 1.354(7) . ?
N1 C9 1.446(7) . ?
N2 N3 1.285(7) . ?
N3 N4 1.373(8) . ?
N4 C11 1.321(8) . ?
N5 N6 1.354(7) . ?
N5 C34 1.355(7) . ?
N5 C32 1.443(8) . ?
N6 N7 1.291(8) . ?
N7 N8 1.354(8) . ?
N8 C34 1.326(8) . ?
O1 C7 1.212(8) . ?
O2 C30 1.205(7) . ?
C1 C6 1.374(9) . ?
C1 C2 1.386(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.360(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.478(9) . ?
C7 C8 1.509(8) . ?
C8 C9 1.322(7) . ?
C9 C18 1.492(8) . ?
C11 C12 1.447(9) . ?
C12 C17 1.389(9) . ?
C12 C13 1.398(9) . ?
C13 C14 1.384(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(12) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.365(8) . ?
C18 C19 1.385(7) . ?
C19 C20 1.381(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.389(9) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.372(11) . ?
C24 C29 1.389(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.362(11) . ?
C25 H25 0.9300 . ?
C26 C27 1.356(11) . ?
C26 H26 0.9300 . ?
C27 C28 1.382(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.383(9) . ?
C28 H28 0.9300 . ?
C29 C30 1.461(9) . ?
C30 C31 1.512(9) . ?
C31 C32 1.324(8) . ?
C32 C41 1.477(9) . ?
C34 C35 1.455(8) . ?
C35 C36 1.382(8) . ?
C35 C40 1.390(8) . ?
C36 C37 1.370(9) . ?
C36 H36 0.9300 . ?
C37 C38 1.369(10) . ?
C37 H37 0.9300 . ?
C38 C39 1.352(11) . ?
C38 H38 0.9300 . ?
C39 C40 1.371(10) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C41 C46 1.366(10) . ?
C41 C42 1.376(9) . ?
C42 C43 1.390(12) . ?
C42 H42 0.9300 . ?
C43 C44 1.355(14) . ?
C43 H43 0.9300 . ?
C44 C45 1.355(15) . ?
C44 H44 0.9300 . ?
C45 C46 1.382(13) . ?
C45 H45 0.9300 . ?
C46 H46 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
C11 N1 N2 108.7(5) . . ?
C11 N1 C9 131.1(5) . . ?
N2 N1 C9 119.9(5) . . ?
N3 N2 N1 106.3(5) . . ?
N2 N3 N4 111.2(5) . . ?
C11 N4 N3 105.7(5) . . ?
N6 N5 C34 108.3(5) . . ?
N6 N5 C32 120.5(5) . . ?
C34 N5 C32 130.4(5) . . ?
N7 N6 N5 106.6(5) . . ?
N6 N7 N8 111.0(6) . . ?
C34 N8 N7 106.6(5) . . ?
C6 C1 C2 120.3(7) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.6(8) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.7(7) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.5(7) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.5(7) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.4(6) . . ?
C1 C6 C7 121.8(6) . . ?
C5 C6 C7 119.7(6) . . ?
O1 C7 C6 120.7(6) . . ?
O1 C7 C8 119.8(6) . . ?
C6 C7 C8 119.5(5) . . ?
C9 C8 C7 125.2(5) . . ?
C9 C8 I1 121.7(4) . . ?
C7 C8 I1 112.1(4) . . ?
C8 C9 N1 117.7(5) . . ?
C8 C9 C18 129.2(5) . . ?
N1 C9 C18 113.0(4) . . ?
N4 C11 N1 108.0(5) . . ?
N4 C11 C12 124.2(6) . . ?
N1 C11 C12 127.8(6) . . ?
C17 C12 C13 118.5(7) . . ?
C17 C12 C11 122.8(6) . . ?
C13 C12 C11 118.7(6) . . ?
C14 C13 C12 120.0(7) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.5(7) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.9(8) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.4(8) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.7(7) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C23 C18 C19 120.1(6) . . ?
C23 C18 C9 120.9(5) . . ?
C19 C18 C9 119.0(5) . . ?
C20 C19 C18 119.5(6) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C21 C20 C19 120.1(6) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.3(6) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 119.6(7) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C18 C23 C22 120.4(6) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C29 120.2(7) . . ?
C25 C24 H24 119.9 . . ?
C29 C24 H24 119.9 . . ?
C26 C25 C24 120.5(7) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C27 C26 C25 120.1(8) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.7(7) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C27 C28 C29 119.8(7) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C28 C29 C24 118.7(7) . . ?
C28 C29 C30 122.6(6) . . ?
C24 C29 C30 118.7(6) . . ?
O2 C30 C29 122.7(7) . . ?
O2 C30 C31 116.2(6) . . ?
C29 C30 C31 121.0(5) . . ?
C32 C31 C30 123.9(5) . . ?
C32 C31 I2 123.1(5) . . ?
C30 C31 I2 112.8(4) . . ?
C31 C32 N5 116.8(6) . . ?
C31 C32 C41 129.8(6) . . ?
N5 C32 C41 113.3(5) . . ?
N8 C34 N5 107.6(5) . . ?
N8 C34 C35 124.7(6) . . ?
N5 C34 C35 127.6(5) . . ?
C36 C35 C40 118.6(6) . . ?
C36 C35 C34 119.3(5) . . ?
C40 C35 C34 122.0(5) . . ?
C37 C36 C35 120.4(6) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C38 C37 C36 120.2(6) . . ?
C38 C37 H37 119.9 . . ?
C36 C37 H37 119.9 . . ?
C39 C38 C37 120.0(7) . . ?
C39 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 C39 C40 121.0(7) . . ?
C38 C39 H39 119.5 . . ?
C40 C39 H39 119.5 . . ?
C39 C40 C35 119.8(6) . . ?
C39 C40 H40 120.1 . . ?
C35 C40 H40 120.1 . . ?
C46 C41 C42 118.8(7) . . ?
C46 C41 C32 121.3(6) . . ?
C42 C41 C32 119.8(7) . . ?
C41 C42 C43 120.4(9) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C44 C43 C42 119.9(9) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C45 C44 C43 119.9(10) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C44 C45 C46 120.8(9) . . ?
C44 C45 H45 119.6 . . ?
C46 C45 H45 119.6 . . ?
C41 C46 C45 120.1(7) . . ?
C41 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 N2 N3 1.6(7) . . . . ?
C9 N1 N2 N3 176.8(4) . . . . ?
N1 N2 N3 N4 -1.6(7) . . . . ?
N2 N3 N4 C11 1.0(7) . . . . ?
C34 N5 N6 N7 0.1(7) . . . . ?
C32 N5 N6 N7 171.1(6) . . . . ?
N5 N6 N7 N8 -0.7(8) . . . . ?
N6 N7 N8 C34 1.1(8) . . . . ?
C6 C1 C2 C3 0.0(14) . . . . ?
C1 C2 C3 C4 -1.4(15) . . . . ?
C2 C3 C4 C5 1.4(13) . . . . ?
C3 C4 C5 C6 0.1(11) . . . . ?
C2 C1 C6 C5 1.5(11) . . . . ?
C2 C1 C6 C7 178.1(7) . . . . ?
C4 C5 C6 C1 -1.6(10) . . . . ?
C4 C5 C6 C7 -178.2(6) . . . . ?
C1 C6 C7 O1 -152.5(7) . . . . ?
C5 C6 C7 O1 24.0(9) . . . . ?
C1 C6 C7 C8 27.4(8) . . . . ?
C5 C6 C7 C8 -156.1(6) . . . . ?
O1 C7 C8 C9 -124.4(7) . . . . ?
C6 C7 C8 C9 55.7(8) . . . . ?
O1 C7 C8 I1 44.3(7) . . . . ?
C6 C7 C8 I1 -135.6(5) . . . . ?
C7 C8 C9 N1 1.6(9) . . . . ?
I1 C8 C9 N1 -166.1(4) . . . . ?
C7 C8 C9 C18 175.7(5) . . . . ?
I1 C8 C9 C18 8.1(9) . . . . ?
C11 N1 C9 C8 -138.9(6) . . . . ?
N2 N1 C9 C8 47.1(8) . . . . ?
C11 N1 C9 C18 46.0(8) . . . . ?
N2 N1 C9 C18 -127.9(6) . . . . ?
N3 N4 C11 N1 0.0(6) . . . . ?
N3 N4 C11 C12 -178.5(5) . . . . ?
N2 N1 C11 N4 -1.0(7) . . . . ?
C9 N1 C11 N4 -175.4(5) . . . . ?
N2 N1 C11 C12 177.5(6) . . . . ?
C9 N1 C11 C12 3.0(10) . . . . ?
N4 C11 C12 C17 -140.1(7) . . . . ?
N1 C11 C12 C17 41.7(10) . . . . ?
N4 C11 C12 C13 40.0(9) . . . . ?
N1 C11 C12 C13 -138.2(6) . . . . ?
C17 C12 C13 C14 -0.4(10) . . . . ?
C11 C12 C13 C14 179.5(6) . . . . ?
C12 C13 C14 C15 -1.0(11) . . . . ?
C13 C14 C15 C16 1.4(12) . . . . ?
C14 C15 C16 C17 -0.4(12) . . . . ?
C15 C16 C17 C12 -1.1(11) . . . . ?
C13 C12 C17 C16 1.4(10) . . . . ?
C11 C12 C17 C16 -178.5(7) . . . . ?
C8 C9 C18 C23 51.3(9) . . . . ?
N1 C9 C18 C23 -134.4(6) . . . . ?
C8 C9 C18 C19 -130.4(6) . . . . ?
N1 C9 C18 C19 44.0(7) . . . . ?
C23 C18 C19 C20 -1.3(9) . . . . ?
C9 C18 C19 C20 -179.7(5) . . . . ?
C18 C19 C20 C21 1.1(9) . . . . ?
C19 C20 C21 C22 -0.1(10) . . . . ?
C20 C21 C22 C23 -0.7(11) . . . . ?
C19 C18 C23 C22 0.6(10) . . . . ?
C9 C18 C23 C22 178.9(6) . . . . ?
C21 C22 C23 C18 0.5(11) . . . . ?
C29 C24 C25 C26 -1.5(13) . . . . ?
C24 C25 C26 C27 2.1(14) . . . . ?
C25 C26 C27 C28 -1.6(13) . . . . ?
C26 C27 C28 C29 0.7(12) . . . . ?
C27 C28 C29 C24 -0.1(11) . . . . ?
C27 C28 C29 C30 -178.6(7) . . . . ?
C25 C24 C29 C28 0.6(11) . . . . ?
C25 C24 C29 C30 179.1(7) . . . . ?
C28 C29 C30 O2 -164.7(7) . . . . ?
C24 C29 C30 O2 16.8(11) . . . . ?
C28 C29 C30 C31 17.5(10) . . . . ?
C24 C29 C30 C31 -161.0(6) . . . . ?
O2 C30 C31 C32 59.1(9) . . . . ?
C29 C30 C31 C32 -123.0(7) . . . . ?
O2 C30 C31 I2 -115.2(6) . . . . ?
C29 C30 C31 I2 62.7(7) . . . . ?
C30 C31 C32 N5 14.6(9) . . . . ?
I2 C31 C32 N5 -171.6(4) . . . . ?
C30 C31 C32 C41 -169.4(6) . . . . ?
I2 C31 C32 C41 4.4(9) . . . . ?
N6 N5 C32 C31 72.5(7) . . . . ?
C34 N5 C32 C31 -118.8(7) . . . . ?
N6 N5 C32 C41 -104.1(7) . . . . ?
C34 N5 C32 C41 64.5(8) . . . . ?
N7 N8 C34 N5 -1.0(7) . . . . ?
N7 N8 C34 C35 176.7(6) . . . . ?
N6 N5 C34 N8 0.6(7) . . . . ?
C32 N5 C34 N8 -169.2(6) . . . . ?
N6 N5 C34 C35 -177.0(6) . . . . ?
C32 N5 C34 C35 13.2(10) . . . . ?
N8 C34 C35 C36 24.9(9) . . . . ?
N5 C34 C35 C36 -157.9(6) . . . . ?
N8 C34 C35 C40 -152.2(7) . . . . ?
N5 C34 C35 C40 25.0(10) . . . . ?
C40 C35 C36 C37 -0.4(10) . . . . ?
C34 C35 C36 C37 -177.6(6) . . . . ?
C35 C36 C37 C38 0.0(11) . . . . ?
C36 C37 C38 C39 0.8(14) . . . . ?
C37 C38 C39 C40 -1.0(16) . . . . ?
C38 C39 C40 C35 0.5(16) . . . . ?
C36 C35 C40 C39 0.2(12) . . . . ?
C34 C35 C40 C39 177.3(8) . . . . ?
C31 C32 C41 C46 52.9(10) . . . . ?
N5 C32 C41 C46 -131.0(6) . . . . ?
C31 C32 C41 C42 -127.9(7) . . . . ?
N5 C32 C41 C42 48.2(8) . . . . ?
C46 C41 C42 C43 -2.1(11) . . . . ?
C32 C41 C42 C43 178.7(7) . . . . ?
C41 C42 C43 C44 2.8(13) . . . . ?
C42 C43 C44 C45 -1.3(16) . . . . ?
C43 C44 C45 C46 -0.9(17) . . . . ?
C42 C41 C46 C45 -0.1(11) . . . . ?
C32 C41 C46 C45 179.0(8) . . . . ?
C44 C45 C46 C41 1.6(14) . . . . ?

_refine_diff_density_max         0.659
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/pentane'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_cd213594
_database_code_depnum_ccdc_archive 'CCDC 1026409'
_audit_update_record             
;
2014-09-26 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        HYC-767-1
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 I2 N2 O3 S'
_chemical_formula_weight         582.18

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.2509(8)
_cell_length_b                   11.4870(14)
_cell_length_c                   12.2569(15)
_cell_angle_alpha                97.897(2)
_cell_angle_beta                 91.846(2)
_cell_angle_gamma                103.895(2)
_cell_volume                     979.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2492
_cell_measurement_theta_min      4.609
_cell_measurement_theta_max      52.570

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.117
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.974
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    3.336
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.10118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5844
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3789
_reflns_number_gt                3029
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0859P)²+1.5411P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3789
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1613
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.81221(6) 0.83802(5) 0.04200(4) 0.0720(2) Uani 1 1 d . . .
I2 I 0.33447(7) 0.82061(5) -0.04387(5) 0.0740(2) Uani 1 1 d . . .
S1 S 0.6145(2) 0.76139(15) 0.40396(12) 0.0514(4) Uani 1 1 d . . .
N1 N 0.5996(7) 0.5802(4) 0.1193(4) 0.0436(11) Uani 1 1 d . . .
N2 N 0.5351(7) 0.6717(4) 0.2836(4) 0.0457(11) Uani 1 1 d . . .
O1 O 0.2861(5) 0.5673(4) 0.0573(3) 0.0490(10) Uani 1 1 d . . .
H1 H 0.2897 0.5369 -0.0069 0.074 Uiso 1 1 calc R . .
O2 O 0.6815(8) 0.6911(5) 0.4752(4) 0.0674(13) Uani 1 1 d . . .
O3 O 0.4614(7) 0.8142(5) 0.4336(4) 0.0647(12) Uani 1 1 d . . .
C1 C 0.4358(8) 0.7231(6) 0.2027(5) 0.0458(13) Uani 1 1 d . . .
H1A H 0.4938 0.8088 0.2042 0.055 Uiso 1 1 calc R . .
H1B H 0.3022 0.7124 0.2165 0.055 Uiso 1 1 calc R . .
C2 C 0.4607(8) 0.6494(5) 0.0927(5) 0.0415(12) Uani 1 1 d . . .
C3 C 0.6321(8) 0.5933(5) 0.2242(4) 0.0405(12) Uani 1 1 d . . .
C4 C 0.7538(8) 0.5270(5) 0.2751(5) 0.0454(13) Uani 1 1 d . . .
C5 C 0.9278(9) 0.5266(6) 0.2322(5) 0.0500(14) Uani 1 1 d . . .
H5 H 0.9666 0.5690 0.1741 0.060 Uiso 1 1 calc R . .
C6 C 1.0434(10) 0.4627(6) 0.2763(6) 0.0624(17) Uani 1 1 d . . .
H6 H 1.1614 0.4629 0.2487 0.075 Uiso 1 1 calc R . .
C7 C 0.9833(12) 0.3988(7) 0.3613(7) 0.0680(19) Uani 1 1 d . . .
H7 H 1.0627 0.3580 0.3928 0.082 Uiso 1 1 calc R . .
C8 C 0.8040(12) 0.3953(6) 0.4000(6) 0.0638(18) Uani 1 1 d . . .
H8 H 0.7611 0.3486 0.4546 0.077 Uiso 1 1 calc R . .
C9 C 0.6907(11) 0.4601(6) 0.3583(6) 0.0567(16) Uani 1 1 d . . .
H9 H 0.5722 0.4594 0.3856 0.068 Uiso 1 1 calc R . .
C10 C 0.5313(8) 0.7222(5) 0.0010(5) 0.0431(12) Uani 1 1 d . . .
H10 H 0.5395 0.6639 -0.0639 0.052 Uiso 1 1 calc R . .
C11 C 0.8053(9) 0.8747(6) 0.3726(5) 0.0507(14) Uani 1 1 d . . .
C12 C 0.9847(10) 0.8528(7) 0.3703(6) 0.0615(17) Uani 1 1 d . . .
H12 H 1.0047 0.7807 0.3886 0.074 Uiso 1 1 calc R . .
C13 C 1.1333(11) 0.9397(7) 0.3404(6) 0.0687(19) Uani 1 1 d . . .
H13 H 1.2546 0.9262 0.3393 0.082 Uiso 1 1 calc R . .
C14 C 1.1042(11) 1.0472(7) 0.3118(5) 0.0639(18) Uani 1 1 d . . .
C15 C 0.9278(12) 1.0678(7) 0.3164(6) 0.069(2) Uani 1 1 d . . .
H15 H 0.9083 1.1402 0.2983 0.083 Uiso 1 1 calc R . .
C16 C 0.7753(11) 0.9822(6) 0.3478(6) 0.0626(17) Uani 1 1 d . . .
H16 H 0.6553 0.9976 0.3519 0.075 Uiso 1 1 calc R . .
C17 C 1.2690(14) 1.1378(9) 0.2762(7) 0.090(3) Uani 1 1 d . . .
H17A H 1.2325 1.2119 0.2706 0.135 Uiso 1 1 calc R . .
H17B H 1.3045 1.1057 0.2057 0.135 Uiso 1 1 calc R . .
H17C H 1.3751 1.1537 0.3296 0.135 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C10 2.149(5) . ?
I2 C10 2.124(6) . ?
S1 O2 1.416(5) . ?
S1 O3 1.421(5) . ?
S1 N2 1.677(5) . ?
S1 C11 1.750(7) . ?
N1 C3 1.282(7) . ?
N1 C2 1.479(7) . ?
N2 C3 1.412(7) . ?
N2 C1 1.473(8) . ?
O1 C2 1.400(7) . ?
O1 H1 0.8200 . ?
C1 C2 1.531(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C10 1.522(8) . ?
C3 C4 1.472(8) . ?
C4 C5 1.383(9) . ?
C4 C9 1.384(8) . ?
C5 C6 1.381(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.392(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.364(10) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10 0.9800 . ?
C11 C16 1.376(9) . ?
C11 C12 1.383(9) . ?
C12 C13 1.379(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.357(11) . ?
C14 C17 1.504(11) . ?
C15 C16 1.396(11) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O2 S1 O3 120.0(3) . . ?
O2 S1 N2 107.9(3) . . ?
O3 S1 N2 104.2(3) . . ?
O2 S1 C11 109.5(3) . . ?
O3 S1 C11 108.8(3) . . ?
N2 S1 C11 105.4(3) . . ?
C3 N1 C2 109.6(5) . . ?
C3 N2 C1 107.7(4) . . ?
C3 N2 S1 125.7(4) . . ?
C1 N2 S1 116.4(4) . . ?
C2 O1 H1 109.5 . . ?
N2 C1 C2 102.9(4) . . ?
N2 C1 H1A 111.2 . . ?
C2 C1 H1A 111.2 . . ?
N2 C1 H1B 111.2 . . ?
C2 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
O1 C2 N1 108.6(5) . . ?
O1 C2 C10 109.6(4) . . ?
N1 C2 C10 109.4(4) . . ?
O1 C2 C1 108.0(4) . . ?
N1 C2 C1 105.0(4) . . ?
C10 C2 C1 116.0(5) . . ?
N1 C3 N2 113.8(5) . . ?
N1 C3 C4 121.6(5) . . ?
N2 C3 C4 124.6(5) . . ?
C5 C4 C9 120.9(6) . . ?
C5 C4 C3 117.9(5) . . ?
C9 C4 C3 121.0(6) . . ?
C6 C5 C4 119.4(6) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C5 119.8(7) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.0(7) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.4(6) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C4 119.3(7) . . ?
C8 C9 H9 120.3 . . ?
C4 C9 H9 120.3 . . ?
C2 C10 I2 111.3(4) . . ?
C2 C10 I1 112.1(4) . . ?
I2 C10 I1 111.8(3) . . ?
C2 C10 H10 107.1 . . ?
I2 C10 H10 107.1 . . ?
I1 C10 H10 107.1 . . ?
C16 C11 C12 120.9(7) . . ?
C16 C11 S1 120.2(5) . . ?
C12 C11 S1 118.9(5) . . ?
C13 C12 C11 118.9(7) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 120.9(7) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 119.3(7) . . ?
C15 C14 C17 121.6(8) . . ?
C13 C14 C17 119.2(8) . . ?
C14 C15 C16 121.0(7) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 118.9(7) . . ?
C11 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O2 S1 N2 C3 -47.1(5) . . . . ?
O3 S1 N2 C3 -175.6(5) . . . . ?
C11 S1 N2 C3 69.9(5) . . . . ?
O2 S1 N2 C1 172.2(4) . . . . ?
O3 S1 N2 C1 43.7(5) . . . . ?
C11 S1 N2 C1 -70.9(5) . . . . ?
C3 N2 C1 C2 9.0(6) . . . . ?
S1 N2 C1 C2 156.3(4) . . . . ?
C3 N1 C2 O1 -107.3(5) . . . . ?
C3 N1 C2 C10 133.2(5) . . . . ?
C3 N1 C2 C1 8.0(6) . . . . ?
N2 C1 C2 O1 105.7(5) . . . . ?
N2 C1 C2 N1 -10.0(6) . . . . ?
N2 C1 C2 C10 -131.0(5) . . . . ?
C2 N1 C3 N2 -2.4(7) . . . . ?
C2 N1 C3 C4 175.2(5) . . . . ?
C1 N2 C3 N1 -4.6(7) . . . . ?
S1 N2 C3 N1 -148.1(4) . . . . ?
C1 N2 C3 C4 177.9(5) . . . . ?
S1 N2 C3 C4 34.5(8) . . . . ?
N1 C3 C4 C5 47.7(8) . . . . ?
N2 C3 C4 C5 -135.0(6) . . . . ?
N1 C3 C4 C9 -127.9(6) . . . . ?
N2 C3 C4 C9 49.4(8) . . . . ?
C9 C4 C5 C6 -2.8(9) . . . . ?
C3 C4 C5 C6 -178.4(6) . . . . ?
C4 C5 C6 C7 0.9(10) . . . . ?
C5 C6 C7 C8 2.2(11) . . . . ?
C6 C7 C8 C9 -3.5(11) . . . . ?
C7 C8 C9 C4 1.7(11) . . . . ?
C5 C4 C9 C8 1.5(10) . . . . ?
C3 C4 C9 C8 177.0(6) . . . . ?
O1 C2 C10 I2 59.7(5) . . . . ?
N1 C2 C10 I2 178.6(3) . . . . ?
C1 C2 C10 I2 -62.8(5) . . . . ?
O1 C2 C10 I1 -174.2(4) . . . . ?
N1 C2 C10 I1 -55.3(5) . . . . ?
C1 C2 C10 I1 63.3(5) . . . . ?
O2 S1 C11 C16 -151.7(5) . . . . ?
O3 S1 C11 C16 -18.8(6) . . . . ?
N2 S1 C11 C16 92.4(6) . . . . ?
O2 S1 C11 C12 30.0(6) . . . . ?
O3 S1 C11 C12 163.0(5) . . . . ?
N2 S1 C11 C12 -85.8(5) . . . . ?
C16 C11 C12 C13 -1.3(10) . . . . ?
S1 C11 C12 C13 176.9(5) . . . . ?
C11 C12 C13 C14 -0.6(11) . . . . ?
C12 C13 C14 C15 1.7(11) . . . . ?
C12 C13 C14 C17 -178.0(7) . . . . ?
C13 C14 C15 C16 -0.9(11) . . . . ?
C17 C14 C15 C16 178.9(7) . . . . ?
C12 C11 C16 C15 2.2(10) . . . . ?
S1 C11 C16 C15 -176.0(5) . . . . ?
C14 C15 C16 C11 -1.1(11) . . . . ?

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
O1 H1 N1 0.82 2.11 2.833(6) 147.8 2_665

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.706
_refine_diff_density_min         -1.268
_refine_diff_density_rms         0.153
