# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mo_mhii_a
_database_code_depnum_ccdc_archive 'CCDC 1523312'
_audit_update_record             
;
2017-01-04 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '3-methyl-1-phenyl-1H-imidazol-3-ium iodide'
_chemical_name_common            MPHII
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 N2, I'
_chemical_formula_sum            'C10 H11 I N2'
_chemical_formula_weight         286.11

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.2438(12)
_cell_length_b                   31.628(4)
_cell_length_c                   17.204(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.388(2)
_cell_angle_gamma                90.00
_cell_volume                     4477.7(11)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6049
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      23.11

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2208
_exptl_absorpt_coefficient_mu    2.820
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7284
_exptl_absorpt_correction_T_max  0.8490
_exptl_absorpt_process_details   'SADABS; Sheldrick, 1996'

_exptl_special_details           
; 
 Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed with oil'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26556
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         25.10
_reflns_number_total             7940
_reflns_number_gt                5656
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0725P)²+30.2411P] 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         7940
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0699
_refine_ls_wR_factor_ref         0.1900
_refine_ls_wR_factor_gt          0.1785
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C18 C 0.8465(17) 0.1702(5) 0.3983(10) 0.082(4) Uani 1 1 d . . .
H18 H 0.8983 0.1472 0.4225 0.098 Uiso 1 1 calc R . .
C8 C 0.3386(15) 0.1701(5) 0.3147(9) 0.074(4) Uani 1 1 d . . .
H8 H 0.3883 0.1480 0.2894 0.089 Uiso 1 1 calc R . .
C20 C 0.7813(13) 0.2096(4) 0.2853(7) 0.059(3) Uani 1 1 d . . .
H20 H 0.7894 0.2133 0.2321 0.071 Uiso 1 1 calc R . .
C19 C 0.8556(14) 0.1768(4) 0.3217(9) 0.075(4) Uani 1 1 d . . .
H19 H 0.9152 0.1581 0.2929 0.090 Uiso 1 1 calc R . .
C7 C 0.2942(14) 0.2048(4) 0.2752(8) 0.068(3) Uani 1 1 d . . .
H7 H 0.3147 0.2070 0.2228 0.082 Uiso 1 1 calc R . .
C16 C 0.6830(14) 0.2335(4) 0.4066(7) 0.065(3) Uani 1 1 d . . .
H16 H 0.6289 0.2531 0.4359 0.078 Uiso 1 1 calc R . .
C17 C 0.7592(18) 0.1982(5) 0.4403(8) 0.082(4) Uani 1 1 d . . .
H17 H 0.7506 0.1933 0.4932 0.098 Uiso 1 1 calc R . .
C15 C 0.6921(12) 0.2378(3) 0.3275(6) 0.047(2) Uani 1 1 d . . .
I1 I 0.30015(9) 0.06165(2) 0.54005(4) 0.0580(2) Uani 1 1 d . . .
I3 I 0.77862(10) 0.06083(3) 0.95677(4) 0.0661(3) Uani 1 1 d . . .
C35 C 0.5364(11) -0.0159(3) 0.7222(6) 0.043(2) Uani 1 1 d . . .
C34 C 0.6685(11) 0.0236(3) 0.6188(6) 0.045(2) Uani 1 1 d . . .
H34 H 0.6446 0.0043 0.5789 0.054 Uiso 1 1 calc R . .
N7 N 0.7459(9) 0.0584(3) 0.6113(5) 0.048(2) Uani 1 1 d . . .
C33 C 0.6829(14) 0.0542(3) 0.7319(5) 0.053(3) Uani 1 1 d . . .
H33 H 0.6732 0.0596 0.7846 0.063 Uiso 1 1 calc R . .
C27 C 0.0014(16) -0.0338(5) 0.6536(9) 0.080(4) Uani 1 1 d . . .
H27 H 0.0104 -0.0337 0.5999 0.096 Uiso 1 1 calc R . .
C40 C 0.4726(13) -0.0457(3) 0.6725(7) 0.056(3) Uani 1 1 d . . .
H40 H 0.4848 -0.0431 0.6194 0.067 Uiso 1 1 calc R . .
N8 N 0.6272(9) 0.0192(2) 0.6921(5) 0.0412(18) Uani 1 1 d . . .
N6 N 0.1330(10) 0.0312(3) 0.8219(6) 0.054(2) Uani 1 1 d . . .
N5 N 0.2370(12) 0.0667(4) 0.9198(7) 0.074(3) Uani 1 1 d . . .
C32 C 0.7547(14) 0.0795(4) 0.6807(7) 0.063(3) Uani 1 1 d . . .
H32 H 0.8007 0.1059 0.6907 0.075 Uiso 1 1 calc R . .
C25 C 0.0593(11) -0.0024(3) 0.7760(6) 0.047(2) Uani 1 1 d . . .
C26 C 0.0718(12) -0.0027(4) 0.6979(6) 0.057(3) Uani 1 1 d . . .
H26 H 0.1291 0.0187 0.6745 0.069 Uiso 1 1 calc R . .
C38 C 0.3697(14) -0.0832(4) 0.7780(9) 0.070(4) Uani 1 1 d . . .
H38 H 0.3113 -0.1058 0.7966 0.084 Uiso 1 1 calc R . .
C36 C 0.5195(14) -0.0186(4) 0.7997(6) 0.059(3) Uani 1 1 d . . .
H36 H 0.5632 0.0022 0.8330 0.071 Uiso 1 1 calc R . .
C23 C 0.1664(16) 0.0715(4) 0.7953(11) 0.087(5) Uani 1 1 d . . .
H23 H 0.1475 0.0817 0.7449 0.104 Uiso 1 1 calc R . .
C24 C 0.1758(13) 0.0284(4) 0.8974(7) 0.057(3) Uani 1 1 d . . .
H24 H 0.1657 0.0048 0.9289 0.068 Uiso 1 1 calc R . .
C29 C -0.0942(15) -0.0663(4) 0.7686(9) 0.073(4) Uani 1 1 d . . .
H29 H -0.1472 -0.0880 0.7933 0.088 Uiso 1 1 calc R . .
C37 C 0.4347(16) -0.0533(5) 0.8296(8) 0.080(4) Uani 1 1 d . . .
H37 H 0.4229 -0.0560 0.8828 0.096 Uiso 1 1 calc R . .
C30 C -0.0226(14) -0.0334(3) 0.8121(8) 0.062(3) Uani 1 1 d . . .
H30 H -0.0309 -0.0325 0.8658 0.074 Uiso 1 1 calc R . .
C22 C 0.2312(17) 0.0930(4) 0.8569(10) 0.085(4) Uani 1 1 d . . .
H22 H 0.2661 0.1209 0.8567 0.102 Uiso 1 1 calc R . .
C39 C 0.3902(14) -0.0798(4) 0.7002(8) 0.069(3) Uani 1 1 d . . .
H39 H 0.3488 -0.1005 0.6660 0.083 Uiso 1 1 calc R . .
C28 C -0.0862(14) -0.0667(5) 0.6891(9) 0.080(4) Uani 1 1 d . . .
H28 H -0.1369 -0.0879 0.6592 0.096 Uiso 1 1 calc R . .
I2 I -0.01621(10) 0.18703(2) 0.65859(4) 0.0595(2) Uani 1 1 d . . .
I4 I 0.47878(10) 0.19019(3) 0.05835(5) 0.0665(3) Uani 1 1 d . . .
N3 N 0.5132(11) 0.3121(3) 0.1939(7) 0.063(3) Uani 1 1 d . . .
N2 N 0.1029(9) 0.2678(2) 0.4271(5) 0.0448(19) Uani 1 1 d . . .
C5 C 0.1855(11) 0.2343(3) 0.3888(6) 0.045(2) Uani 1 1 d . . .
N4 N 0.6161(9) 0.2736(3) 0.2892(5) 0.047(2) Uani 1 1 d . . .
C4 C 0.0845(13) 0.2714(4) 0.5027(6) 0.055(3) Uani 1 1 d . . .
H4 H 0.1228 0.2522 0.5404 0.066 Uiso 1 1 calc R . .
N1 N 0.0037(11) 0.3063(3) 0.5165(6) 0.058(2) Uani 1 1 d . . .
C14 C 0.5772(12) 0.2756(3) 0.2121(6) 0.049(2) Uani 1 1 d . . .
H14 H 0.5938 0.2539 0.1769 0.059 Uiso 1 1 calc R . .
C11 C 0.4597(15) 0.3259(5) 0.1156(7) 0.076(4) Uani 1 1 d . . .
H11A H 0.5163 0.3101 0.0780 0.114 Uiso 1 1 calc R . .
H11B H 0.4825 0.3555 0.1100 0.114 Uiso 1 1 calc R . .
H11C H 0.3449 0.3212 0.1072 0.114 Uiso 1 1 calc R . .
C10 C 0.2305(14) 0.1982(4) 0.4315(8) 0.066(3) Uani 1 1 d . . .
H10 H 0.2075 0.1953 0.4835 0.079 Uiso 1 1 calc R . .
C3 C 0.0284(14) 0.3021(3) 0.3882(6) 0.055(3) Uani 1 1 d . . .
H3 H 0.0207 0.3077 0.3350 0.065 Uiso 1 1 calc R . .
C6 C 0.2162(12) 0.2384(3) 0.3123(7) 0.053(3) Uani 1 1 d . . .
H6 H 0.1864 0.2628 0.2849 0.063 Uiso 1 1 calc R . .
C12 C 0.5130(15) 0.3353(4) 0.2610(9) 0.074(4) Uani 1 1 d . . .
H12 H 0.4748 0.3628 0.2651 0.089 Uiso 1 1 calc R . .
C2 C -0.0309(15) 0.3257(4) 0.4473(8) 0.069(3) Uani 1 1 d . . .
H2 H -0.0864 0.3512 0.4408 0.083 Uiso 1 1 calc R . .
C13 C 0.5776(16) 0.3115(4) 0.3207(7) 0.068(3) Uani 1 1 d . . .
H13 H 0.5926 0.3194 0.3726 0.082 Uiso 1 1 calc R . .
C9 C 0.3115(15) 0.1665(4) 0.3925(10) 0.077(4) Uani 1 1 d . . .
H9 H 0.3478 0.1426 0.4196 0.092 Uiso 1 1 calc R . .
C31 C 0.8057(16) 0.0753(4) 0.5394(8) 0.082(4) Uani 1 1 d . . .
H31A H 0.8382 0.0525 0.5071 0.122 Uiso 1 1 calc R . .
H31B H 0.8972 0.0934 0.5516 0.122 Uiso 1 1 calc R . .
H31C H 0.7210 0.0913 0.5122 0.122 Uiso 1 1 calc R . .
C21 C 0.292(2) 0.0758(5) 0.9999(9) 0.103(5) Uani 1 1 d . . .
H21A H 0.2063 0.0897 1.0256 0.155 Uiso 1 1 calc R . .
H21B H 0.3854 0.0938 1.0005 0.155 Uiso 1 1 calc R . .
H21C H 0.3195 0.0499 1.0265 0.155 Uiso 1 1 calc R . .
C1 C -0.0339(19) 0.3218(5) 0.5920(8) 0.090(4) Uani 1 1 d . . .
H1A H -0.0303 0.2988 0.6285 0.135 Uiso 1 1 calc R . .
H1B H -0.1407 0.3340 0.5889 0.135 Uiso 1 1 calc R . .
H1C H 0.0441 0.3428 0.6089 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
C18 C19 1.34(2) . ?
C18 C17 1.37(2) . ?
C8 C7 1.332(18) . ?
C8 C9 1.374(19) . ?
C20 C19 1.338(16) . ?
C20 C15 1.388(15) . ?
C7 C6 1.411(16) . ?
C16 C15 1.375(15) . ?
C16 C17 1.392(18) . ?
C15 N4 1.435(13) . ?
C35 C36 1.351(14) . ?
C35 C40 1.358(14) . ?
C35 N8 1.450(12) . ?
C34 N7 1.282(12) . ?
C34 N8 1.333(12) . ?
N7 C32 1.366(14) . ?
N7 C31 1.460(14) . ?
C33 C32 1.353(15) . ?
C33 N8 1.366(13) . ?
C27 C26 1.355(18) . ?
C27 C28 1.42(2) . ?
C40 C39 1.374(15) . ?
N6 C24 1.328(14) . ?
N6 C23 1.389(15) . ?
N6 C25 1.438(13) . ?
N5 C24 1.358(14) . ?
N5 C22 1.363(18) . ?
N5 C21 1.454(17) . ?
C25 C26 1.353(14) . ?
C25 C30 1.359(15) . ?
C38 C39 1.364(18) . ?
C38 C37 1.382(19) . ?
C36 C37 1.416(17) . ?
C23 C22 1.34(2) . ?
C29 C28 1.373(19) . ?
C29 C30 1.395(16) . ?
N3 C14 1.301(13) . ?
N3 C12 1.369(17) . ?
N3 C11 1.459(15) . ?
N2 C4 1.323(13) . ?
N2 C3 1.398(12) . ?
N2 C5 1.440(13) . ?
C5 C6 1.361(15) . ?
C5 C10 1.398(15) . ?
N4 C14 1.348(13) . ?
N4 C13 1.359(14) . ?
C4 N1 1.316(14) . ?
N1 C2 1.355(16) . ?
N1 C1 1.440(16) . ?
C10 C9 1.397(18) . ?
C3 C2 1.375(16) . ?
C12 C13 1.357(18) . ?

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
C19 C18 C17 118.6(13) . . ?
C7 C8 C9 120.5(13) . . ?
C19 C20 C15 119.7(12) . . ?
C20 C19 C18 122.0(14) . . ?
C8 C7 C6 120.6(13) . . ?
C15 C16 C17 116.2(13) . . ?
C18 C17 C16 122.4(12) . . ?
C16 C15 C20 121.0(11) . . ?
C16 C15 N4 118.9(10) . . ?
C20 C15 N4 119.9(9) . . ?
C36 C35 C40 121.2(10) . . ?
C36 C35 N8 119.1(9) . . ?
C40 C35 N8 119.7(9) . . ?
N7 C34 N8 110.0(9) . . ?
C34 N7 C32 109.4(9) . . ?
C34 N7 C31 126.5(10) . . ?
C32 N7 C31 123.9(10) . . ?
C32 C33 N8 107.5(9) . . ?
C26 C27 C28 119.9(14) . . ?
C35 C40 C39 120.6(12) . . ?
C34 N8 C33 107.0(8) . . ?
C34 N8 C35 125.7(8) . . ?
C33 N8 C35 127.3(8) . . ?
C24 N6 C23 109.6(11) . . ?
C24 N6 C25 124.5(9) . . ?
C23 N6 C25 125.8(11) . . ?
C24 N5 C22 108.8(11) . . ?
C24 N5 C21 122.4(12) . . ?
C22 N5 C21 128.7(13) . . ?
C33 C32 N7 106.1(10) . . ?
C26 C25 C30 121.3(11) . . ?
C26 C25 N6 119.6(10) . . ?
C30 C25 N6 119.1(10) . . ?
C25 C26 C27 120.5(12) . . ?
C39 C38 C37 120.7(12) . . ?
C35 C36 C37 119.3(11) . . ?
C22 C23 N6 106.4(14) . . ?
N6 C24 N5 106.9(11) . . ?
C28 C29 C30 119.8(14) . . ?
C38 C37 C36 118.6(12) . . ?
C25 C30 C29 119.9(12) . . ?
C23 C22 N5 108.2(12) . . ?
C38 C39 C40 119.6(13) . . ?
C29 C28 C27 118.5(13) . . ?
C14 N3 C12 107.0(10) . . ?
C14 N3 C11 125.8(12) . . ?
C12 N3 C11 127.1(11) . . ?
C4 N2 C3 109.4(9) . . ?
C4 N2 C5 126.7(9) . . ?
C3 N2 C5 123.9(9) . . ?
C6 C5 C10 121.7(11) . . ?
C6 C5 N2 119.6(9) . . ?
C10 C5 N2 118.7(10) . . ?
C14 N4 C13 107.6(9) . . ?
C14 N4 C15 124.1(9) . . ?
C13 N4 C15 128.2(9) . . ?
N1 C4 N2 109.7(10) . . ?
C4 N1 C2 107.8(10) . . ?
C4 N1 C1 125.9(11) . . ?
C2 N1 C1 126.3(11) . . ?
N3 C14 N4 110.4(10) . . ?
C9 C10 C5 116.9(13) . . ?
C2 C3 N2 103.4(9) . . ?
C5 C6 C7 118.8(11) . . ?
C13 C12 N3 108.7(11) . . ?
N1 C2 C3 109.7(10) . . ?
C12 C13 N4 106.2(11) . . ?
C8 C9 C10 121.3(12) . . ?

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
C15 C20 C19 C18 0.2(18) . . . . ?
C17 C18 C19 C20 0(2) . . . . ?
C9 C8 C7 C6 -1.0(19) . . . . ?
C19 C18 C17 C16 -1(2) . . . . ?
C15 C16 C17 C18 3.5(18) . . . . ?
C17 C16 C15 C20 -3.8(16) . . . . ?
C17 C16 C15 N4 -180.0(9) . . . . ?
C19 C20 C15 C16 2.1(17) . . . . ?
C19 C20 C15 N4 178.2(10) . . . . ?
N8 C34 N7 C32 -1.9(11) . . . . ?
N8 C34 N7 C31 -177.4(10) . . . . ?
C36 C35 C40 C39 -0.6(16) . . . . ?
N8 C35 C40 C39 178.1(10) . . . . ?
N7 C34 N8 C33 0.5(11) . . . . ?
N7 C34 N8 C35 179.0(8) . . . . ?
C32 C33 N8 C34 1.1(12) . . . . ?
C32 C33 N8 C35 -177.4(9) . . . . ?
C36 C35 N8 C34 172.4(9) . . . . ?
C40 C35 N8 C34 -6.4(14) . . . . ?
C36 C35 N8 C33 -9.3(14) . . . . ?
C40 C35 N8 C33 171.8(10) . . . . ?
N8 C33 C32 N7 -2.2(12) . . . . ?
C34 N7 C32 C33 2.6(12) . . . . ?
C31 N7 C32 C33 178.1(10) . . . . ?
C24 N6 C25 C26 -156.9(10) . . . . ?
C23 N6 C25 C26 25.0(15) . . . . ?
C24 N6 C25 C30 23.5(15) . . . . ?
C23 N6 C25 C30 -154.6(11) . . . . ?
C30 C25 C26 C27 0.4(17) . . . . ?
N6 C25 C26 C27 -179.2(10) . . . . ?
C28 C27 C26 C25 -0.1(17) . . . . ?
C40 C35 C36 C37 0.4(17) . . . . ?
N8 C35 C36 C37 -178.4(10) . . . . ?
C24 N6 C23 C22 0.3(14) . . . . ?
C25 N6 C23 C22 178.7(10) . . . . ?
C23 N6 C24 N5 -0.2(12) . . . . ?
C25 N6 C24 N5 -178.6(9) . . . . ?
C22 N5 C24 N6 0.0(13) . . . . ?
C21 N5 C24 N6 177.9(11) . . . . ?
C39 C38 C37 C36 1.6(19) . . . . ?
C35 C36 C37 C38 -0.9(18) . . . . ?
C26 C25 C30 C29 0.7(17) . . . . ?
N6 C25 C30 C29 -179.7(10) . . . . ?
C28 C29 C30 C25 -2.2(18) . . . . ?
N6 C23 C22 N5 -0.3(15) . . . . ?
C24 N5 C22 C23 0.2(16) . . . . ?
C21 N5 C22 C23 -177.6(13) . . . . ?
C37 C38 C39 C40 -1.8(19) . . . . ?
C35 C40 C39 C38 1.3(18) . . . . ?
C30 C29 C28 C27 2.5(18) . . . . ?
C26 C27 C28 C29 -1.3(18) . . . . ?
C4 N2 C5 C6 -169.8(9) . . . . ?
C3 N2 C5 C6 10.3(14) . . . . ?
C4 N2 C5 C10 10.9(14) . . . . ?
C3 N2 C5 C10 -169.0(9) . . . . ?
C16 C15 N4 C14 -160.8(9) . . . . ?
C20 C15 N4 C14 23.0(14) . . . . ?
C16 C15 N4 C13 22.7(15) . . . . ?
C20 C15 N4 C13 -153.5(11) . . . . ?
C3 N2 C4 N1 -0.7(12) . . . . ?
C5 N2 C4 N1 179.4(8) . . . . ?
N2 C4 N1 C2 0.0(12) . . . . ?
N2 C4 N1 C1 -177.3(11) . . . . ?
C12 N3 C14 N4 1.3(12) . . . . ?
C11 N3 C14 N4 178.6(10) . . . . ?
C13 N4 C14 N3 -1.5(12) . . . . ?
C15 N4 C14 N3 -178.6(9) . . . . ?
C6 C5 C10 C9 1.2(16) . . . . ?
N2 C5 C10 C9 -179.5(9) . . . . ?
C4 N2 C3 C2 1.0(12) . . . . ?
C5 N2 C3 C2 -179.0(9) . . . . ?
C10 C5 C6 C7 0.6(15) . . . . ?
N2 C5 C6 C7 -178.6(9) . . . . ?
C8 C7 C6 C5 -0.7(17) . . . . ?
C14 N3 C12 C13 -0.5(14) . . . . ?
C11 N3 C12 C13 -177.8(11) . . . . ?
C4 N1 C2 C3 0.7(13) . . . . ?
C1 N1 C2 C3 178.0(12) . . . . ?
N2 C3 C2 N1 -1.0(13) . . . . ?
N3 C12 C13 N4 -0.4(14) . . . . ?
C14 N4 C13 C12 1.1(13) . . . . ?
C15 N4 C13 C12 178.0(10) . . . . ?
C7 C8 C9 C10 3(2) . . . . ?
C5 C10 C9 C8 -3.0(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.930
_refine_diff_density_min         -1.498
_refine_diff_density_rms         0.150
####################################################################### 
# 
# 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_mo_61104aa
_database_code_depnum_ccdc_archive 'CCDC 1517957'
_audit_update_record             
;
2017-01-04 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'3-methyl-1-(thiophen-3-yl)-1H-imidazol-3-ium iodide'
_chemical_name_common            ' MT3II'
_chemical_melting_point          ?
_chemical_formula_moiety         291.95
_chemical_formula_sum            'C8 H9 I N2 S'
_chemical_formula_weight         292.13

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   19.028(6)
_cell_length_b                   7.932(3)
_cell_length_c                   13.915(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2100.1(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6875
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.290
_exptl_absorpt_coefficient_mu    3.199
_shelx_estimated_absorpt_T_min   0.315
_shelx_estimated_absorpt_T_max   0.457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.192
_exptl_absorpt_correction_T_max  0.430
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14077
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.141
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             4498
_reflns_number_gt                4121
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_max     0.862
_reflns_Friedel_fraction_full    0.893

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0466P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0059(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1658 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4498
_refine_ls_number_parameters     224
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.090
_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 0.66848(2) 0.46050(6) 0.78174(3) 0.03228(15) Uani 1 1 d . . . . .
I2 I 0.36379(2) 0.97090(6) 0.59239(4) 0.03552(16) Uani 1 1 d . . . . .
S1 S 0.66109(11) 0.7640(3) 0.45123(16) 0.0395(5) Uani 1 1 d . . . . .
N1 N 0.4845(3) 0.5858(7) 0.5520(4) 0.0230(11) Uani 1 1 d . . . . .
N2 N 0.3814(3) 0.4869(7) 0.5842(6) 0.0268(12) Uani 1 1 d . . . . .
N3 N 0.8881(3) 0.0963(7) 0.1164(4) 0.0241(11) Uani 1 1 d . . . . .
N4 N 0.8385(3) -0.0081(8) 0.2433(5) 0.0292(13) Uani 1 1 d . . . . .
C1 C 0.4192(4) 0.5671(8) 0.5178(5) 0.0260(14) Uani 1 1 d . . . . .
H1 H 0.4028 0.6043 0.4570 0.031 Uiso 1 1 calc R U . . .
C2 C 0.4229(5) 0.4558(9) 0.6618(6) 0.0337(17) Uani 1 1 d . . . . .
H2 H 0.4088 0.4012 0.7194 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4874(4) 0.5157(10) 0.6427(5) 0.0308(16) Uani 1 1 d . . . . .
H3 H 0.5273 0.5107 0.6836 0.037 Uiso 1 1 calc R U . . .
C4 C 0.6081(3) 0.6586(10) 0.5301(5) 0.0317(15) Uani 1 1 d . . . . .
H4 H 0.6240 0.6031 0.5866 0.038 Uiso 1 1 calc R U . . .
C5 C 0.5401(3) 0.6653(8) 0.5009(4) 0.0230(13) Uani 1 1 d . . . . .
C6 C 0.5296(4) 0.7560(9) 0.4130(5) 0.0308(15) Uani 1 1 d . . . . .
H6 H 0.4853 0.7715 0.3828 0.037 Uiso 1 1 calc R U . . .
C7 C 0.5934(4) 0.8187(9) 0.3776(5) 0.0304(15) Uani 1 1 d . . . . .
H7 H 0.5982 0.8829 0.3203 0.036 Uiso 1 1 calc R U . . .
C8 C 0.3063(4) 0.4499(9) 0.5734(7) 0.0365(19) Uani 1 1 d . . . . .
H8A H 0.2792 0.5215 0.6172 0.055 Uiso 1 1 calc R U . . .
H8B H 0.2976 0.3311 0.5887 0.055 Uiso 1 1 calc R U . . .
H8C H 0.2919 0.4725 0.5070 0.055 Uiso 1 1 calc R U . . .
C9 C 0.8271(4) 0.0704(9) 0.1620(6) 0.0270(14) Uani 1 1 d . . . . .
H9 H 0.7823 0.1039 0.1388 0.032 Uiso 1 1 calc R U . . .
C10 C 0.9090(4) -0.0372(10) 0.2524(7) 0.039(2) Uani 1 1 d . . . . .
H10 H 0.9318 -0.0921 0.3044 0.047 Uiso 1 1 calc R U . . .
C11 C 0.9401(4) 0.0273(11) 0.1730(7) 0.0394(19) Uani 1 1 d . . . . .
H11 H 0.9890 0.0254 0.1588 0.047 Uiso 1 1 calc R U . . .
C12 C 0.9599(4) 0.2005(9) -0.0169(5) 0.0302(15) Uani 0.799(10) 1 d . . P A 1
H12 H 1.0039 0.1752 0.0119 0.036 Uiso 0.799(10) 1 calc R U P A 1
C14 C 0.8381(4) 0.2258(9) -0.0328(6) 0.0300(15) Uani 0.799(10) 1 d . . P A 1
H14 H 0.7900 0.2132 -0.0160 0.036 Uiso 0.799(10) 1 calc R U P A 1
C15 C 0.8615(14) 0.295(4) -0.1134(19) 0.054(5) Uani 0.799(10) 1 d . . P A 1
H15 H 0.8314 0.3452 -0.1595 0.065 Uiso 0.799(10) 1 calc R U P A 1
S2 S 0.94951(11) 0.2857(3) -0.12700(16) 0.0333(7) Uani 0.799(10) 1 d . U P A 1
C14' C 0.9599(4) 0.2005(9) -0.0169(5) 0.0302(15) Uani 0.201(10) 1 d . . P A 2
H14' H 1.0039 0.1752 0.0119 0.036 Uiso 0.201(10) 1 calc R U P A 2
C12' C 0.8381(4) 0.2258(9) -0.0328(6) 0.0300(15) Uani 0.201(10) 1 d D . P A 2
H12' H 0.7904 0.2159 -0.0133 0.036 Uiso 0.201(10) 1 calc R U P A 2
S2' S 0.8631(13) 0.307(4) -0.1394(18) 0.054(5) Uani 0.201(10) 1 d D . P A 2
C15' C 0.94951(11) 0.2857(3) -0.12700(16) 0.0333(7) Uani 0.201(10) 1 d D . P A
2
H15' H 0.9851 0.3147 -0.1719 0.040 Uiso 0.201(10) 1 calc R U P A 2
C13 C 0.8960(3) 0.1733(8) 0.0249(5) 0.0261(14) Uani 1 1 d . . . . .
C16 C 0.7845(5) -0.0514(10) 0.3145(7) 0.042(2) Uani 1 1 d . . . . .
H16A H 0.7389 -0.0082 0.2931 0.062 Uiso 1 1 calc R U . . .
H16B H 0.7967 -0.0006 0.3766 0.062 Uiso 1 1 calc R U . . .
H16C H 0.7820 -0.1742 0.3215 0.062 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
S1 C7 1.702(8) . ?
S1 C4 1.709(7) . ?
N1 C1 1.339(9) . ?
N1 C3 1.379(9) . ?
N1 C5 1.422(8) . ?
N2 C1 1.333(10) . ?
N2 C2 1.360(11) . ?
N2 C8 1.466(10) . ?
N3 C9 1.337(8) . ?
N3 C11 1.379(10) . ?
N3 C13 1.420(9) . ?
N4 C9 1.310(11) . ?
N4 C10 1.366(10) . ?
N4 C16 1.468(11) . ?
C2 C3 1.342(12) . ?
C4 C5 1.357(9) . ?
C5 C6 1.433(9) . ?
C6 C7 1.402(10) . ?
C10 C11 1.354(12) . ?
C12 C13 1.365(10) . ?
C12 S2 1.686(8) . ?
C14 C15 1.33(3) . ?
C14 C13 1.426(10) . ?
C15 S2 1.69(3) . ?
C14' C13 1.365(10) . ?
C14' C15' 1.686(8) . ?
C12' C13 1.426(10) . ?
C12' S2' 1.69(2) . ?
S2' C15' 1.66(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C4 93.7(3) . . ?
C1 N1 C3 108.5(6) . . ?
C1 N1 C5 124.2(6) . . ?
C3 N1 C5 127.4(6) . . ?
C1 N2 C2 108.8(6) . . ?
C1 N2 C8 123.4(8) . . ?
C2 N2 C8 127.7(7) . . ?
C9 N3 C11 106.9(6) . . ?
C9 N3 C13 125.7(6) . . ?
C11 N3 C13 127.3(6) . . ?
C9 N4 C10 108.8(7) . . ?
C9 N4 C16 125.3(7) . . ?
C10 N4 C16 125.8(7) . . ?
N2 C1 N1 107.9(6) . . ?
C3 C2 N2 108.0(7) . . ?
C2 C3 N1 106.8(7) . . ?
C5 C4 S1 110.5(6) . . ?
C4 C5 N1 122.8(6) . . ?
C4 C5 C6 114.1(6) . . ?
N1 C5 C6 123.1(6) . . ?
C7 C6 C5 111.0(6) . . ?
C6 C7 S1 110.7(5) . . ?
N4 C9 N3 109.8(6) . . ?
C11 C10 N4 106.9(7) . . ?
C10 C11 N3 107.6(7) . . ?
C13 C12 S2 110.2(5) . . ?
C15 C14 C13 109.7(13) . . ?
C14 C15 S2 114.3(19) . . ?
C15 S2 C12 91.8(10) . . ?
C13 C14' C15' 110.2(5) . . ?
C13 C12' S2' 112.8(10) . . ?
C15' S2' C12' 98.6(14) . . ?
S2' C15' C14' 104.6(9) . . ?
C14' C13 N3 123.0(6) . . ?
C12 C13 N3 123.0(6) . . ?
C14' C13 C12' 113.8(7) . . ?
N3 C13 C12' 123.2(6) . . ?
C12 C13 C14 113.8(7) . . ?
N3 C13 C14 123.2(6) . . ?

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
C2 N2 C1 N1 0.5(8) . . . . ?
C8 N2 C1 N1 177.6(6) . . . . ?
C3 N1 C1 N2 -0.2(8) . . . . ?
C5 N1 C1 N2 179.7(6) . . . . ?
C1 N2 C2 C3 -0.7(8) . . . . ?
C8 N2 C2 C3 -177.6(7) . . . . ?
N2 C2 C3 N1 0.5(8) . . . . ?
C1 N1 C3 C2 -0.2(8) . . . . ?
C5 N1 C3 C2 179.9(6) . . . . ?
C7 S1 C4 C5 -0.1(6) . . . . ?
S1 C4 C5 N1 178.9(5) . . . . ?
S1 C4 C5 C6 0.3(8) . . . . ?
C1 N1 C5 C4 -168.9(7) . . . . ?
C3 N1 C5 C4 10.9(11) . . . . ?
C1 N1 C5 C6 9.5(10) . . . . ?
C3 N1 C5 C6 -170.6(7) . . . . ?
C4 C5 C6 C7 -0.4(9) . . . . ?
N1 C5 C6 C7 -179.0(6) . . . . ?
C5 C6 C7 S1 0.3(8) . . . . ?
C4 S1 C7 C6 -0.1(6) . . . . ?
C10 N4 C9 N3 -0.5(9) . . . . ?
C16 N4 C9 N3 177.3(7) . . . . ?
C11 N3 C9 N4 0.7(8) . . . . ?
C13 N3 C9 N4 178.0(6) . . . . ?
C9 N4 C10 C11 0.1(10) . . . . ?
C16 N4 C10 C11 -177.7(8) . . . . ?
N4 C10 C11 N3 0.4(10) . . . . ?
C9 N3 C11 C10 -0.7(9) . . . . ?
C13 N3 C11 C10 -177.9(7) . . . . ?
C13 C14 C15 S2 5(3) . . . . ?
C14 C15 S2 C12 -5(2) . . . . ?
C13 C12 S2 C15 3.2(13) . . . . ?
C13 C12' S2' C15' 0.4(18) . . . . ?
C12' S2' C15' C14' -1.0(15) . . . . ?
C13 C14' C15' S2' 1.5(12) . . . . ?
C15' C14' C13 N3 177.4(5) . . . . ?
C15' C14' C13 C12' -1.3(8) . . . . ?
S2 C12 C13 N3 177.4(5) . . . . ?
S2 C12 C13 C14 -1.3(8) . . . . ?
C9 N3 C13 C14' 178.1(7) . . . . ?
C11 N3 C13 C14' -5.1(10) . . . . ?
C9 N3 C13 C12 178.1(7) . . . . ?
C11 N3 C13 C12 -5.1(10) . . . . ?
C9 N3 C13 C12' -3.4(10) . . . . ?
C11 N3 C13 C12' 173.4(7) . . . . ?
C9 N3 C13 C14 -3.4(10) . . . . ?
C11 N3 C13 C14 173.4(7) . . . . ?
S2' C12' C13 C14' 0.5(14) . . . . ?
S2' C12' C13 N3 -178.1(12) . . . . ?
C15 C14 C13 C12 -2.1(17) . . . . ?
C15 C14 C13 N3 179.3(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 I1 0.95 2.84 3.691(7) 150.2 2_664
C3 H3 I1 0.95 3.04 3.977(8) 168.8 .
C4 H4 I1 0.95 3.06 4.006(8) 173.1 .
C9 H9 I2 0.95 2.91 3.774(7) 151.0 2_664
C10 H10 S2 0.95 2.89 3.735(8) 148.4 2_755
C11 H11 I2 0.95 2.98 3.921(8) 170.3 4_644
C12 H12 I2 0.95 3.20 4.109(7) 161.7 4_644
C14' H14' I2 0.95 3.20 4.109(7) 161.7 4_644

_refine_diff_density_max         1.093
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.146



####################################################################### 
# 
# 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_mo_70503aa
_database_code_depnum_ccdc_archive 'CCDC 1523955'
_audit_update_record             
;
2017-05-07 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            MT2II
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H9 I N2 S'
_chemical_formula_weight         292.13

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   18.903(10)
_cell_length_b                   6.311(3)
_cell_length_c                   17.950(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2141.3(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    6621
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.44

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.730
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.138
_shelx_estimated_absorpt_T_min   0.208
_shelx_estimated_absorpt_T_max   0.573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_T_max  0.647
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14462
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.269
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4864
_reflns_number_gt                4355
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component perfect inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0665P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Refined as a perfect inversion twin. 
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4864
_refine_ls_number_parameters     238
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.123
_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 0.29076(3) 0.28467(9) 0.15251(2) 0.03828(19) Uani 1 1 d . . . . .
I2 I 0.04292(3) 0.23947(8) 0.34313(3) 0.03734(19) Uani 1 1 d . . . . .
N1 N 0.2279(4) 0.0204(11) 0.3893(4) 0.0330(14) Uani 1 1 d . . . . .
N2 N 0.1800(4) -0.1867(13) 0.3088(5) 0.0380(16) Uani 1 1 d . . . . .
N3 N 0.5249(3) 0.5092(11) 0.6052(4) 0.0322(14) Uani 1 1 d . . . . .
N4 N 0.5715(5) 0.2927(12) 0.6849(5) 0.0371(17) Uani 1 1 d . . . . .
C1 C 0.2148(4) -0.0052(16) 0.3173(5) 0.037(2) Uani 1 1 d . . . . .
H1 H 0.240(4) 0.067(14) 0.277(4) 0.03(2) Uiso 1 1 d . . . . .
C2 C 0.1997(5) -0.1460(16) 0.4287(5) 0.043(2) Uani 1 1 d . . . . .
H2 H 0.2015 -0.1666 0.4806 0.051 Uiso 1 1 calc R U . . .
C3 C 0.1685(8) -0.2751(16) 0.3775(8) 0.048(3) Uani 1 1 d . . . . .
H3 H 0.1437 -0.4012 0.3874 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2654(5) 0.1940(14) 0.4189(5) 0.0353(18) Uani 1 1 d D . . . .
C5 C 0.3222(15) 0.298(5) 0.3928(12) 0.040(5) Uani 0.734(12) 1 d . U P A 1
H5 H 0.3429 0.2597 0.3471 0.048 Uiso 0.734(12) 1 calc R U P A 1
C6 C 0.3493(5) 0.4610(16) 0.4349(6) 0.056(2) Uani 0.734(12) 1 d . . P A 1
H6 H 0.3882 0.5466 0.4221 0.068 Uiso 0.734(12) 1 calc R U P A 1
C7 C 0.3106(5) 0.4767(19) 0.4972(5) 0.057(3) Uani 0.734(12) 1 d . . P A 1
H7 H 0.3207 0.5755 0.5350 0.069 Uiso 0.734(12) 1 calc R U P A 1
S1 S 0.24417(15) 0.3088(5) 0.50239(17) 0.0390(9) Uani 0.734(12) 1 d . . P A 1
C5' C 0.24417(15) 0.3088(5) 0.50239(17) 0.0390(9) Uani 0.266(12) 1 d . . P A 2
H5' H 0.2083 0.2851 0.5377 0.047 Uiso 0.266(12) 1 calc R U P A 2
C6' C 0.3106(5) 0.4767(19) 0.4972(5) 0.057(3) Uani 0.266(12) 1 d . . P A 2
H6' H 0.3207 0.5755 0.5350 0.069 Uiso 0.266(12) 1 calc R U P A 2
C7' C 0.3493(5) 0.4610(16) 0.4349(6) 0.056(2) Uani 0.266(12) 1 d D . P A 2
H7' H 0.3882 0.5518 0.4280 0.068 Uiso 0.266(12) 1 calc R U P A 2
S1' S 0.3306(12) 0.292(4) 0.3723(10) 0.052(5) Uani 0.266(12) 1 d D U P A 2
C8 C 0.1533(7) -0.2704(18) 0.2382(8) 0.055(3) Uani 1 1 d . . . . .
H8A H 0.1439 -0.1541 0.2043 0.083 Uiso 1 1 calc R U . . .
H8B H 0.1100 -0.3487 0.2471 0.083 Uiso 1 1 calc R U . . .
H8C H 0.1884 -0.3640 0.2165 0.083 Uiso 1 1 calc R U . . .
C9 C 0.5372(5) 0.4751(15) 0.6782(5) 0.0378(19) Uani 1 1 d . . . . .
H9 H 0.517(4) 0.583(13) 0.722(4) 0.03(2) Uiso 1 1 d . . . . .
C10 C 0.5564(5) 0.3460(16) 0.5650(6) 0.043(2) Uani 1 1 d . . . . .
H10 H 0.5573 0.3314 0.5128 0.052 Uiso 1 1 calc R U . . .
C11 C 0.5850(6) 0.2137(15) 0.6148(7) 0.041(2) Uani 1 1 d . . . . .
H11 H 0.6100 0.0888 0.6039 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4868(5) 0.6841(14) 0.5761(5) 0.0360(18) Uani 1 1 d . . . . .
C13 C 0.4269(5) 0.7873(13) 0.6151(6) 0.0323(19) Uani 1 1 d . . . . .
H13 H 0.4075 0.7521 0.6617 0.039 Uiso 1 1 calc R U . . .
C14 C 0.4050(5) 0.9548(16) 0.5650(6) 0.052(2) Uani 1 1 d . . . . .
H14 H 0.3668 1.0447 0.5763 0.062 Uiso 1 1 calc R U . . .
C15 C 0.4423(5) 0.9751(17) 0.5013(6) 0.055(2) Uani 1 1 d . . . . .
H15 H 0.4321 1.0773 0.4647 0.065 Uiso 1 1 calc R U . . .
S2 S 0.50889(15) 0.7990(4) 0.49361(16) 0.0493(6) Uani 1 1 d . . . . .
C16 C 0.5975(8) 0.2063(18) 0.7550(7) 0.059(3) Uani 1 1 d . . . . .
H16A H 0.6485 0.2227 0.7574 0.089 Uiso 1 1 calc R U . . .
H16B H 0.5855 0.0571 0.7581 0.089 Uiso 1 1 calc R U . . .
H16C H 0.5759 0.2816 0.7963 0.089 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
N1 C1 1.325(11) . ?
N1 C2 1.375(11) . ?
N1 C4 1.408(11) . ?
N2 C1 1.329(12) . ?
N2 C3 1.371(15) . ?
N2 C8 1.463(15) . ?
N3 C9 1.348(11) . ?
N3 C10 1.392(11) . ?
N3 C12 1.418(11) . ?
N4 C9 1.326(11) . ?
N4 C11 1.377(15) . ?
N4 C16 1.458(14) . ?
C1 H1 0.98(8) . ?
C2 C3 1.363(17) . ?
C2 H2 0.9400 . ?
C3 H3 0.9400 . ?
C4 C5 1.34(3) . ?
C4 S1' 1.61(2) . ?
C4 S1 1.712(10) . ?
C4 C5' 1.712(10) . ?
C5 C6 1.38(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.340(14) . ?
C6 H6 0.9400 . ?
C7 S1 1.646(12) . ?
C7 H7 0.9400 . ?
C5' C6' 1.646(12) . ?
C5' H5' 0.9400 . ?
C6' C7' 1.340(14) . ?
C6' H6' 0.9400 . ?
C7' S1' 1.59(2) . ?
C7' H7' 0.9400 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9 1.12(8) . ?
C10 C11 1.338(16) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 C13 1.481(13) . ?
C12 S2 1.702(9) . ?
C13 C14 1.448(13) . ?
C13 H13 0.9400 . ?
C14 C15 1.350(13) . ?
C14 H14 0.9400 . ?
C15 S2 1.685(11) . ?
C15 H15 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 109.6(8) . . ?
C1 N1 C4 123.9(8) . . ?
C2 N1 C4 126.5(7) . . ?
C1 N2 C3 109.0(8) . . ?
C1 N2 C8 125.6(9) . . ?
C3 N2 C8 125.3(9) . . ?
C9 N3 C10 108.2(7) . . ?
C9 N3 C12 124.7(7) . . ?
C10 N3 C12 127.0(7) . . ?
C9 N4 C11 108.8(8) . . ?
C9 N4 C16 124.6(9) . . ?
C11 N4 C16 126.2(8) . . ?
N1 C1 N2 108.1(8) . . ?
N1 C1 H1 124(5) . . ?
N2 C1 H1 124(5) . . ?
C3 C2 N1 106.1(8) . . ?
C3 C2 H2 127.0 . . ?
N1 C2 H2 127.0 . . ?
C2 C3 N2 107.2(8) . . ?
C2 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
C5 C4 N1 130.5(12) . . ?
N1 C4 S1' 119.1(10) . . ?
C5 C4 S1 106.7(12) . . ?
N1 C4 S1 122.8(7) . . ?
N1 C4 C5' 122.8(7) . . ?
S1' C4 C5' 118.1(9) . . ?
C4 C5 C6 118.1(16) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C7 C6 C5 108.1(13) . . ?
C7 C6 H6 126.0 . . ?
C5 C6 H6 126.0 . . ?
C6 C7 S1 114.6(8) . . ?
C6 C7 H7 122.7 . . ?
S1 C7 H7 122.7 . . ?
C7 S1 C4 92.5(5) . . ?
C6' C5' C4 92.5(5) . . ?
C6' C5' H5' 133.7 . . ?
C4 C5' H5' 133.7 . . ?
C7' C6' C5' 114.6(8) . . ?
C7' C6' H6' 122.7 . . ?
C5' C6' H6' 122.7 . . ?
C6' C7' S1' 121.2(11) . . ?
C6' C7' H7' 119.4 . . ?
S1' C7' H7' 119.4 . . ?
C7' S1' C4 93.5(10) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C9 N3 108.1(8) . . ?
N4 C9 H9 129(4) . . ?
N3 C9 H9 122(4) . . ?
C11 C10 N3 106.7(9) . . ?
C11 C10 H10 126.7 . . ?
N3 C10 H10 126.7 . . ?
C10 C11 N4 108.1(8) . . ?
C10 C11 H11 126.0 . . ?
N4 C11 H11 126.0 . . ?
N3 C12 C13 123.9(8) . . ?
N3 C12 S2 121.8(6) . . ?
C13 C12 S2 114.3(7) . . ?
C14 C13 C12 104.3(8) . . ?
C14 C13 H13 127.9 . . ?
C12 C13 H13 127.9 . . ?
C15 C14 C13 116.5(9) . . ?
C15 C14 H14 121.8 . . ?
C13 C14 H14 121.8 . . ?
C14 C15 S2 113.4(8) . . ?
C14 C15 H15 123.3 . . ?
S2 C15 H15 123.3 . . ?
C15 S2 C12 91.5(5) . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C2 N1 C1 N2 -1.4(10) . . . . ?
C4 N1 C1 N2 178.6(7) . . . . ?
C3 N2 C1 N1 2.2(12) . . . . ?
C8 N2 C1 N1 177.7(9) . . . . ?
C1 N1 C2 C3 0.0(11) . . . . ?
C4 N1 C2 C3 180.0(9) . . . . ?
N1 C2 C3 N2 1.4(13) . . . . ?
C1 N2 C3 C2 -2.2(14) . . . . ?
C8 N2 C3 C2 -177.7(10) . . . . ?
C1 N1 C4 C5 -39(2) . . . . ?
C2 N1 C4 C5 141.3(19) . . . . ?
C1 N1 C4 S1' -36.1(15) . . . . ?
C2 N1 C4 S1' 143.9(12) . . . . ?
C1 N1 C4 S1 143.2(8) . . . . ?
C2 N1 C4 S1 -36.8(12) . . . . ?
C1 N1 C4 C5' 143.2(8) . . . . ?
C2 N1 C4 C5' -36.8(12) . . . . ?
N1 C4 C5 C6 -178.4(14) . . . . ?
S1 C4 C5 C6 0(3) . . . . ?
C4 C5 C6 C7 1(3) . . . . ?
C5 C6 C7 S1 -1.9(19) . . . . ?
C6 C7 S1 C4 1.7(7) . . . . ?
C5 C4 S1 C7 -0.9(13) . . . . ?
N1 C4 S1 C7 177.6(8) . . . . ?
N1 C4 C5' C6' 177.6(8) . . . . ?
S1' C4 C5' C6' -3.1(13) . . . . ?
C4 C5' C6' C7' 1.7(7) . . . . ?
C5' C6' C7' S1' 0.0(6) . . . . ?
C6' C7' S1' C4 -1.9(10) . . . . ?
N1 C4 S1' C7' -177.6(8) . . . . ?
C5' C4 S1' C7' 3.1(13) . . . . ?
C11 N4 C9 N3 3.5(12) . . . . ?
C16 N4 C9 N3 176.6(10) . . . . ?
C10 N3 C9 N4 -3.3(11) . . . . ?
C12 N3 C9 N4 177.1(7) . . . . ?
C9 N3 C10 C11 1.9(11) . . . . ?
C12 N3 C10 C11 -178.6(8) . . . . ?
N3 C10 C11 N4 0.2(12) . . . . ?
C9 N4 C11 C10 -2.3(13) . . . . ?
C16 N4 C11 C10 -175.3(11) . . . . ?
C9 N3 C12 C13 -32.7(13) . . . . ?
C10 N3 C12 C13 147.9(9) . . . . ?
C9 N3 C12 S2 144.9(8) . . . . ?
C10 N3 C12 S2 -34.5(11) . . . . ?
N3 C12 C13 C14 -179.9(8) . . . . ?
S2 C12 C13 C14 2.3(10) . . . . ?
C12 C13 C14 C15 -0.9(12) . . . . ?
C13 C14 C15 S2 -0.8(12) . . . . ?
C14 C15 S2 C12 1.9(8) . . . . ?
N3 C12 S2 C15 179.7(7) . . . . ?
C13 C12 S2 C15 -2.5(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 I1 0.98(8) 2.80(8) 3.763(9) 170(6) .
C2 H2 I1 0.94 3.10 4.044(10) 177.7 4_545
C3 H3 I2 0.94 3.07 3.924(12) 152.4 1_545
C9 H9 I2 1.12(8) 2.63(8) 3.720(9) 164(6) 4
C10 H10 I2 0.94 3.09 4.026(10) 173.3 3

_refine_diff_density_max         1.093
_refine_diff_density_min         -1.259
_refine_diff_density_rms         0.207



