# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_Compound-3
_database_code_depnum_ccdc_archive 'CCDC 1536515'
_audit_update_record             
;
2017-03-07 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H10 I N2 O S'
_chemical_formula_weight         285.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.4742 1.8119 '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'
O O 0.0106 0.0060 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.8008(10)
_cell_length_b                   10.319(2)
_cell_length_c                   11.1239(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.590(10)
_cell_angle_gamma                90.00
_cell_volume                     1003.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.47
_cell_measurement_theta_max      13.47

_exptl_crystal_description       prism
_exptl_crystal_colour            dark-red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    3.352
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   empirical

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      294(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  'Enraf-Nonius CAD4 diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  '3600 sec'
_diffrn_standards_decay_%        no
_diffrn_reflns_number            1756
_diffrn_reflns_av_R_equivalents  0.0110
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         24.97
_reflns_number_total             1756
_reflns_number_gt                1562
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0286P)²+0.6608P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0362(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1756
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0192
_refine_ls_wR_factor_ref         0.0523
_refine_ls_wR_factor_gt          0.0503
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
I I 0.45178(2) 0.416509(19) 0.906978(17) 0.05086(12) Uani 1 1 d . . .
S S 0.34282(9) 0.24100(9) 0.67930(7) 0.0579(2) Uani 1 1 d . . .
O O -0.1501(2) 0.4786(2) 0.59530(17) 0.0482(5) Uani 1 1 d . . .
N1 N 0.0865(2) 0.3795(2) 0.61533(19) 0.0379(5) Uani 1 1 d . . .
H1 H 0.1239 0.4154 0.5555 0.046 Uiso 1 1 calc R . .
N2 N 0.0725(3) 0.2533(2) 0.77162(19) 0.0405(5) Uani 1 1 d . . .
C1 C 0.1637(3) 0.2893(3) 0.6909(2) 0.0393(6) Uani 1 1 d . . .
C2 C -0.0553(3) 0.4049(2) 0.6463(2) 0.0352(5) Uani 1 1 d . . .
C3 C -0.0741(3) 0.3250(2) 0.7580(2) 0.0358(5) Uani 1 1 d . . .
C21 C 0.1132(4) 0.1619(3) 0.8694(3) 0.0594(8) Uani 1 1 d . . .
H21A H 0.0282 0.1513 0.9154 0.089 Uiso 1 1 calc R . .
H21B H 0.1998 0.1942 0.9210 0.089 Uiso 1 1 calc R . .
H21C H 0.1384 0.0798 0.8362 0.089 Uiso 1 1 calc R . .
C31 C -0.2107(3) 0.2343(3) 0.7335(3) 0.0539(7) Uani 1 1 d . . .
H31A H -0.2215 0.1843 0.8048 0.081 Uiso 1 1 calc R . .
H31B H -0.1949 0.1772 0.6680 0.081 Uiso 1 1 calc R . .
H31C H -0.3018 0.2844 0.7123 0.081 Uiso 1 1 calc R . .
C32 C -0.0850(4) 0.4142(3) 0.8661(3) 0.0508(7) Uani 1 1 d . . .
H32A H -0.0964 0.3631 0.9366 0.076 Uiso 1 1 calc R . .
H32B H -0.1719 0.4704 0.8495 0.076 Uiso 1 1 calc R . .
H32C H 0.0064 0.4654 0.8802 0.076 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I 0.04503(15) 0.05495(16) 0.05247(16) 0.00510(9) 0.00500(9) 0.00083(8)
S 0.0426(4) 0.0727(5) 0.0581(5) -0.0187(4) 0.0044(3) 0.0098(4)
O 0.0489(11) 0.0557(11) 0.0411(10) 0.0113(9) 0.0099(9) 0.0085(9)
N1 0.0403(11) 0.0426(11) 0.0320(11) 0.0010(9) 0.0090(9) -0.0017(9)
N2 0.0448(12) 0.0399(11) 0.0364(11) 0.0048(10) 0.0036(9) 0.0040(10)
C1 0.0415(13) 0.0412(13) 0.0345(13) -0.0105(11) 0.0014(11) -0.0017(11)
C2 0.0394(13) 0.0369(13) 0.0297(12) -0.0022(10) 0.0058(10) -0.0053(11)
C3 0.0412(13) 0.0367(12) 0.0308(12) 0.0013(10) 0.0095(10) -0.0012(10)
C21 0.075(2) 0.0556(18) 0.0464(17) 0.0136(14) 0.0026(15) 0.0121(16)
C31 0.0502(16) 0.0522(17) 0.0612(19) 0.0011(14) 0.0154(14) -0.0134(14)
C32 0.0710(19) 0.0481(16) 0.0360(14) -0.0022(12) 0.0180(13) 0.0013(14)

_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
I I 2.7512(5) 3_667 ?
S C1 1.672(3) . ?
O C2 1.220(3) . ?
N1 C2 1.359(3) . ?
N1 C1 1.380(3) . ?
N2 C1 1.324(3) . ?
N2 C21 1.452(4) . ?
N2 C3 1.480(3) . ?
C2 C3 1.516(3) . ?
C3 C31 1.523(4) . ?
C3 C32 1.526(4) . ?

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
C2 N1 C1 112.2(2) . . ?
C1 N2 C21 124.9(2) . . ?
C1 N2 C3 112.3(2) . . ?
C21 N2 C3 122.6(2) . . ?
N2 C1 N1 107.9(2) . . ?
N2 C1 S 128.3(2) . . ?
N1 C1 S 123.8(2) . . ?
O C2 N1 127.0(2) . . ?
O C2 C3 126.0(2) . . ?
N1 C2 C3 107.0(2) . . ?
N2 C3 C2 100.37(19) . . ?
N2 C3 C31 111.8(2) . . ?
C2 C3 C31 110.2(2) . . ?
N2 C3 C32 110.8(2) . . ?
C2 C3 C32 109.9(2) . . ?
C31 C3 C32 113.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_Compound-1
_database_code_depnum_ccdc_archive 'CCDC 1536513'
_audit_update_record             
;
2017-03-07 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H8 Br I N2 O S'
_chemical_formula_weight         350.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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'
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'

_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                   7.786(3)
_cell_length_b                   8.719(4)
_cell_length_c                   9.403(4)
_cell_angle_alpha                62.62(4)
_cell_angle_beta                 89.52(4)
_cell_angle_gamma                66.88(4)
_cell_volume                     509.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.70
_cell_measurement_theta_max      14.65

_exptl_crystal_description       pseudoprism
_exptl_crystal_colour            dark-orange
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    7.221
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   empirical

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      294(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  'Enraf-Nonius CAD4 diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  '3600 sec'
_diffrn_standards_decay_%        no
_diffrn_reflns_number            1588
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         23.97
_reflns_number_total             1588
_reflns_number_gt                1413
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1313P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1588
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.1864
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.323
_refine_ls_restrained_S_all      1.323
_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
I I 0.15670(7) 0.62966(7) 0.02361(6) 0.0334(4) Uani 1 1 d . . .
Br Br 0.28146(16) 0.52442(17) -0.20587(13) 0.0489(5) Uani 1 1 d . . .
S S 0.0010(4) 0.7345(4) 0.2276(4) 0.0449(7) Uani 1 1 d . . .
O O 0.2271(9) 1.0270(10) 0.4806(8) 0.0406(16) Uani 1 1 d . . .
N2 N 0.3133(10) 0.8005(10) 0.2473(9) 0.0318(16) Uani 1 1 d . . .
H2 H 0.3686 0.7535 0.1874 0.038 Uiso 1 1 calc R . .
N1 N 0.0945(9) 0.9002(10) 0.3716(9) 0.0319(16) Uani 1 1 d . . .
H1 H -0.0111 0.9238 0.4051 0.038 Uiso 1 1 calc R . .
C1 C 0.1451(11) 0.8120(12) 0.2801(11) 0.0317(19) Uani 1 1 d . . .
C2 C 0.2329(13) 0.9470(12) 0.4040(10) 0.0334(19) Uani 1 1 d . . .
C3 C 0.3965(12) 0.8768(12) 0.3242(11) 0.033(2) Uani 1 1 d . . .
C31 C 0.4364(13) 1.0401(13) 0.1995(11) 0.039(2) Uani 1 1 d . . .
H31A H 0.3225 1.1368 0.1170 0.059 Uiso 1 1 calc R . .
H31B H 0.5360 0.9917 0.1493 0.059 Uiso 1 1 calc R . .
H31C H 0.4760 1.0950 0.2534 0.059 Uiso 1 1 calc R . .
C32 C 0.5720(13) 0.7182(14) 0.4578(12) 0.038(2) Uani 1 1 d . . .
H32A H 0.5414 0.6173 0.5333 0.057 Uiso 1 1 calc R . .
H32B H 0.6127 0.7691 0.5152 0.057 Uiso 1 1 calc R . .
H32C H 0.6729 0.6678 0.4096 0.057 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I 0.0303(6) 0.0378(6) 0.0408(6) -0.0259(4) 0.0079(3) -0.0151(4)
Br 0.0491(8) 0.0601(8) 0.0478(7) -0.0366(6) 0.0222(5) -0.0218(6)
S 0.0342(14) 0.0709(18) 0.0630(17) -0.0529(15) 0.0206(13) -0.0298(13)
O 0.037(4) 0.061(4) 0.057(4) -0.049(4) 0.021(3) -0.028(3)
N2 0.030(4) 0.045(4) 0.039(4) -0.033(3) 0.017(3) -0.020(3)
N1 0.022(4) 0.042(4) 0.047(4) -0.034(4) 0.009(3) -0.013(3)
C1 0.022(4) 0.033(4) 0.043(5) -0.025(4) 0.006(4) -0.008(3)
C2 0.031(4) 0.039(5) 0.037(5) -0.026(4) 0.013(4) -0.013(4)
C3 0.028(5) 0.038(5) 0.049(5) -0.029(4) 0.021(4) -0.019(4)
C31 0.043(5) 0.038(5) 0.039(5) -0.018(4) 0.005(4) -0.020(4)
C32 0.031(5) 0.048(5) 0.049(5) -0.030(4) 0.014(4) -0.023(4)

_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
I S 2.587(3) . ?
I Br 2.7436(16) . ?
S C1 1.694(8) . ?
O C2 1.201(10) . ?
N2 C1 1.319(11) . ?
N2 C3 1.475(11) . ?
N1 C1 1.362(10) . ?
N1 C2 1.372(12) . ?
C2 C3 1.535(11) . ?
C3 C31 1.517(12) . ?
C3 C32 1.518(13) . ?

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
S I Br 173.43(6) . . ?
C1 S I 104.5(3) . . ?
C1 N2 C3 112.8(7) . . ?
C1 N1 C2 111.7(7) . . ?
N2 C1 N1 109.0(7) . . ?
N2 C1 S 130.1(7) . . ?
N1 C1 S 120.9(6) . . ?
O C2 N1 126.5(8) . . ?
O C2 C3 126.6(8) . . ?
N1 C2 C3 106.9(7) . . ?
N2 C3 C31 112.4(7) . . ?
N2 C3 C32 111.4(7) . . ?
C31 C3 C32 112.0(7) . . ?
N2 C3 C2 99.6(6) . . ?
C31 C3 C2 111.8(7) . . ?
C32 C3 C2 108.8(7) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        23.97
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.028
_refine_diff_density_min         -1.749
_refine_diff_density_rms         0.513
####################################################################### 
# 
# 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_Compound-2
_database_code_depnum_ccdc_archive 'CCDC 1536514'
_audit_update_record             
;
2017-03-07 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H10 I2 N2 O S'
_chemical_formula_weight         412.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.4742 1.8119 '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'
O O 0.0106 0.0060 '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'
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'

_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                   7.900(2)
_cell_length_b                   11.379(3)
_cell_length_c                   12.977(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.60(3)
_cell_angle_gamma                90.00
_cell_volume                     1161.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.57
_cell_measurement_theta_max      13.16

_exptl_crystal_description       prism
_exptl_crystal_colour            dark-red
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    5.560
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   empirical

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      294(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  'Enraf-Nonius CAD4 diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  '3600 sec'
_diffrn_standards_decay_%        no
_diffrn_reflns_number            2524
_diffrn_reflns_av_R_equivalents  0.0120
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         26.97
_reflns_number_total             2524
_reflns_number_gt                2080
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0358P)²+1.6890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0114(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2524
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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 0.94693(3) 0.14024(2) 0.87789(2) 0.04387(12) Uani 1 1 d . . .
I2 I 1.06603(4) -0.05622(3) 0.77767(2) 0.05905(13) Uani 1 1 d . . .
S S 0.81565(14) 0.33473(10) 0.97846(9) 0.0483(3) Uani 1 1 d . . .
O O 0.3926(4) 0.0521(3) 1.0962(3) 0.0583(9) Uani 1 1 d . . .
N1 N 0.5920(4) 0.1654(3) 1.0241(3) 0.0389(7) Uani 1 1 d . . .
H1 H 0.6281 0.1148 0.9822 0.047 Uiso 1 1 calc R . .
N2 N 0.5657(4) 0.3334(3) 1.1036(2) 0.0360(7) Uani 1 1 d . . .
C1 C 0.6554(5) 0.2770(3) 1.0378(3) 0.0349(8) Uani 1 1 d . . .
C2 C 0.4629(5) 0.1445(4) 1.0862(3) 0.0395(8) Uani 1 1 d . . .
C3 C 0.4277(5) 0.2603(4) 1.1372(3) 0.0380(8) Uani 1 1 d . . .
C21 C 0.5933(6) 0.4541(4) 1.1371(3) 0.0477(10) Uani 1 1 d . . .
H21A H 0.5129 0.4745 1.1851 0.072 Uiso 1 1 calc R . .
H21B H 0.5784 0.5054 1.0782 0.072 Uiso 1 1 calc R . .
H21C H 0.7067 0.4624 1.1703 0.072 Uiso 1 1 calc R . .
C31 C 0.2542(6) 0.3066(4) 1.0908(4) 0.0516(10) Uani 1 1 d . . .
H31A H 0.2304 0.3800 1.1229 0.077 Uiso 1 1 calc R . .
H31B H 0.1673 0.2506 1.1028 0.077 Uiso 1 1 calc R . .
H31C H 0.2563 0.3181 1.0176 0.077 Uiso 1 1 calc R . .
C32 C 0.4356(6) 0.2497(5) 1.2535(3) 0.0529(11) Uani 1 1 d . . .
H32A H 0.4117 0.3247 1.2827 0.079 Uiso 1 1 calc R . .
H32B H 0.5472 0.2242 1.2803 0.079 Uiso 1 1 calc R . .
H32C H 0.3529 0.1933 1.2715 0.079 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.04239(16) 0.04242(18) 0.04809(17) 0.00149(11) 0.01093(11) -0.00503(11)
I2 0.0673(2) 0.0532(2) 0.0595(2) -0.00161(14) 0.02042(15) 0.01234(15)
S 0.0490(6) 0.0351(6) 0.0636(6) -0.0023(5) 0.0199(5) -0.0065(4)
O 0.068(2) 0.0343(17) 0.077(2) -0.0127(15) 0.0314(17) -0.0156(15)
N1 0.0461(18) 0.0273(16) 0.0449(17) -0.0060(14) 0.0128(14) -0.0022(14)
N2 0.0415(16) 0.0275(16) 0.0399(16) -0.0039(13) 0.0077(13) -0.0023(13)
C1 0.0379(18) 0.0274(19) 0.0388(18) 0.0023(15) 0.0013(14) 0.0011(15)
C2 0.0414(19) 0.034(2) 0.045(2) -0.0042(16) 0.0101(15) -0.0026(17)
C3 0.0399(19) 0.033(2) 0.0422(19) -0.0048(16) 0.0083(15) -0.0020(16)
C21 0.063(3) 0.032(2) 0.048(2) -0.0107(17) 0.0064(19) -0.0071(19)
C31 0.047(2) 0.046(3) 0.062(3) -0.006(2) 0.003(2) 0.003(2)
C32 0.066(3) 0.052(3) 0.041(2) 0.002(2) 0.0097(19) 0.002(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.7953(7) . ?
I1 S 2.8180(13) . ?
S C1 1.679(4) . ?
O C2 1.203(5) . ?
N1 C1 1.371(5) . ?
N1 C2 1.380(5) . ?
N2 C1 1.327(5) . ?
N2 C21 1.451(5) . ?
N2 C3 1.471(5) . ?
C2 C3 1.512(5) . ?
C3 C32 1.510(5) . ?
C3 C31 1.536(6) . ?

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
I2 I1 S 178.03(3) . . ?
C1 S I1 103.51(14) . . ?
C1 N1 C2 111.4(3) . . ?
C1 N2 C21 125.2(3) . . ?
C1 N2 C3 112.0(3) . . ?
C21 N2 C3 122.7(3) . . ?
N2 C1 N1 108.7(3) . . ?
N2 C1 S 125.5(3) . . ?
N1 C1 S 125.8(3) . . ?
O C2 N1 126.1(4) . . ?
O C2 C3 127.5(4) . . ?
N1 C2 C3 106.5(3) . . ?
N2 C3 C32 112.4(3) . . ?
N2 C3 C2 101.0(3) . . ?
C32 C3 C2 112.1(4) . . ?
N2 C3 C31 110.4(3) . . ?
C32 C3 C31 111.6(3) . . ?
C2 C3 C31 108.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.97
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.106
