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

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

data_1c_0_0_GPa
_database_code_depnum_ccdc_archive 'CCDC 1501479'
_audit_update_record             
;
2016-08-29 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            IBPSSEt
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 I N3 Se4'
_chemical_formula_sum            'C7 H5 I N3 Se4'
_chemical_formula_weight         573.88

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'
Se Se -0.0929 2.2259 '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      tetragonal
_space_group_IT_number           113
_space_group_name_H-M_alt        'P -4 21 m'
_space_group_name_Hall           'P -4 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.4704(6)
_cell_length_b                   16.4704(6)
_cell_length_c                   4.2345(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1148.71(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    680
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      30.0

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.318
_exptl_crystal_F_000             1028
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    15.430
_shelx_estimated_absorpt_T_min   0.119
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6029
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'BRUKER SMART APEX II'
_diffrn_measurement_method       'Omega scan'
_diffrn_standards_number         3
_diffrn_standards_interval_time  4.5
_diffrn_standards_decay_%        0'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21522
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_av_R_equivalents  0.1333
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         4.462
_diffrn_reflns_theta_max         29.973
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1732
_reflns_number_gt                1176
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

 The value for R_int is large because the crystals were very
 thin needles.
;

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       "SMART, 'Bruker APEX II"
_computing_data_reduction        "SAINT, 'Bruker APEX II"
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    Mercury
_computing_publication_material  ?

_refine_special_details          
; 
 ? 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0252P)²+3.1755P] 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     SHELXL
_refine_ls_extinction_coef       0.0009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_number_reflns         1732
_refine_ls_number_parameters     77
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
I1 I 0.08033(4) 0.41967(4) -0.1784(2) 0.0461(3) Uani 1 2 d S . .
Se1 Se 0.06605(5) 0.10138(5) 0.2652(2) 0.0311(2) Uani 1 1 d . . .
Se2 Se 0.02926(5) 0.22497(6) 0.0239(3) 0.0364(3) Uani 1 1 d . . .
N1 N 0.1627(4) 0.1381(4) 0.4070(17) 0.0288(17) Uani 1 1 d . . .
N2 N 0.2553(4) 0.2447(4) 0.440(2) 0.024(2) Uani 1 2 d S . .
C1 C 0.1825(5) 0.2125(5) 0.3311(18) 0.0234(18) Uani 1 1 d . . .
C2 C 0.1309(5) 0.2656(5) 0.1486(19) 0.0260(19) Uani 1 1 d . . .
C3 C 0.1580(5) 0.3420(5) 0.064(3) 0.031(3) Uani 1 2 d S . .
C4 C 0.3055(5) 0.1945(5) 0.651(3) 0.025(3) Uani 1 2 d S . .
H4A H 0.3365 0.2301 0.7844 0.030 Uiso 1 1 d R . .
C5 C 0.3624(5) 0.1376(5) 0.484(3) 0.039(3) Uani 1 2 d S . .
H5B H 0.3307 0.1023 0.3509 0.058 Uiso 1 1 d R . .
H5A H 0.3941 0.1060 0.6341 0.058 Uiso 1 2 d SR . .


_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 C3 2.080(12) . ?
Se1 N1 1.805(7) . ?
Se1 Se2 2.3570(12) . ?
Se2 C2 1.878(8) . ?
N1 C1 1.308(10) . ?
N2 C1 1.391(9) . ?
N2 C1 1.391(9) 7 ?
N2 C4 1.472(14) . ?
C1 C2 1.443(11) . ?
C2 C3 1.383(10) . ?
C3 C2 1.383(10) 7 ?
C4 C5 1.502(16) . ?
C4 H4A 0.9600 . ?
C5 H5B 0.9649 . ?
C5 H5A 0.9726 . ?

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
N1 Se1 Se2 94.7(2) . . ?
C2 Se2 Se1 87.5(2) . . ?
C1 N1 Se1 116.9(6) . . ?
C1 N2 C1 123.2(10) . 7 ?
C1 N2 C4 118.2(5) . . ?
C1 N2 C4 118.2(5) 7 . ?
N1 C1 N2 119.4(7) . . ?
N1 C1 C2 123.5(8) . . ?
N2 C1 C2 117.1(8) . . ?
C3 C2 C1 120.0(8) . . ?
C3 C2 Se2 122.6(6) . . ?
C1 C2 Se2 117.4(6) . . ?
C2 C3 C2 121.4(11) 7 . ?
C2 C3 I1 119.3(5) 7 . ?
C2 C3 I1 119.3(5) . . ?
N2 C4 C5 114.5(10) . . ?
N2 C4 H4A 108.2 . . ?
C5 C4 H4A 109.0 . . ?
C4 C5 H5B 108.3 . . ?
C4 C5 H5A 111.2 . . ?
H5B C5 H5A 110.4 . . ?

_refine_diff_density_max         1.019
_refine_diff_density_min         -1.004
_refine_diff_density_rms         0.200


