# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_x1
_database_code_depnum_ccdc_archive 'CCDC 2000010'
loop_
_audit_author_name
_audit_author_address
'Yaobin Li'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2020-04-29 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_audit_creation_date             2019-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I5 Sb, C5 H11 N3'
_chemical_formula_sum            'C5 H11 I5 N3 Sb'
_chemical_formula_weight         869.42
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.9312(2)
_cell_length_b                   10.7807(3)
_cell_length_c                   18.0106(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1734.14(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3529
_cell_measurement_temperature    320(2)
_cell_measurement_theta_max      25.674
_cell_measurement_theta_min      2.546
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.470
_exptl_absorpt_correction_T_max  0.4302
_exptl_absorpt_correction_T_min  0.2957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0990 before and 0.0653 after correction. The Ratio of minimum to maximum transmission is 0.6874. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    3.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14571
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.138
_diffrn_reflns_theta_min         2.202
_diffrn_ambient_temperature      320.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2986
_reflns_number_total             3823
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.418
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.210
_refine_ls_abs_structure_details 
;
 Flack x determined using 1012 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(8)
_refine_ls_extinction_coef       0.00091(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     99
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0636P)²+9.2013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1431
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
2. Restrained distances
 N3-C5
 1.47 with sigma of 0.02
 C5-C4 = C3-C4
 1.48 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C3 \\sim C4 \\sim N3 \\sim C5: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C1 \\sim N1 \\sim C2 \\sim N2 \\sim C3: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(C4) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C1) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(N3)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), N2(H2A), C1(H1A)
4.c Fitted pentagon refined as free rotating group:
 N1(C2,C3,N2,C1)
4.d Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Sb1 Sb 0.29547(6) 0.56932(4) 0.56705(3) 0.04392(11) Uani 1 1 d . . . . .
I2 I 0.05491(7) 0.40906(5) 0.61613(4) 0.07385(19) Uani 1 1 d . . . . .
I1 I 0.26886(7) 0.71860(6) 0.70706(3) 0.07430(18) Uani 1 1 d . . . . .
I3 I 0.52799(8) 0.41774(6) 0.62784(4) 0.0777(2) Uani 1 1 d . . . . .
I5 I 0.54864(7) 0.74816(6) 0.50495(5) 0.07747(19) Uani 1 1 d . . . . .
I4 I 0.30733(8) 0.42843(6) 0.42114(3) 0.07521(18) Uani 1 1 d . . . . .
N1 N 0.1152(8) 1.1909(6) 0.7974(4) 0.1423(19) Uani 1 1 d . U . . .
H1 H 0.033122 1.200853 0.821640 0.171 Uiso 1 1 calc R . . . .
C2 C 0.1392(11) 1.1052(8) 0.7387(5) 0.1323(19) Uani 1 1 d G U . . .
H2 H 0.068916 1.049935 0.719784 0.159 Uiso 1 1 calc R . . . .
C3 C 0.2893(11) 1.1186(11) 0.7140(6) 0.1346(16) Uani 1 1 d DG U . . .
N2 N 0.3581(9) 1.2126(11) 0.7575(6) 0.1431(19) Uani 1 1 d G U . . .
H2A H 0.448991 1.238066 0.753287 0.172 Uiso 1 1 calc R . . . .
C1 C 0.2505(9) 1.2573(7) 0.8090(5) 0.1444(19) Uani 1 1 d G U . . .
H1A H 0.265914 1.319215 0.844110 0.173 Uiso 1 1 calc R . . . .
C4 C 0.3819(14) 1.0682(12) 0.6555(4) 0.1300(19) Uani 1 1 d D U . . .
H4A H 0.480140 1.095493 0.671698 0.156 Uiso 1 1 calc R . . . .
H4B H 0.379325 0.980662 0.667912 0.156 Uiso 1 1 calc R . . . .
N3 N 0.2464(10) 1.0862(11) 0.5642(8) 0.171(4) Uani 1 1 d D U . . .
H3A H 0.196433 1.076456 0.606580 0.206 Uiso 1 1 calc GR . . . .
H3B H 0.211227 1.033577 0.530428 0.206 Uiso 1 1 calc GR . . . .
H3C H 0.234916 1.163655 0.548072 0.206 Uiso 1 1 calc GR . . . .
C5 C 0.4047(11) 1.0617(13) 0.5767(5) 0.141(2) Uani 1 1 d D U . . .
H5A H 0.436643 0.980618 0.559620 0.170 Uiso 1 1 calc R . . . .
H5B H 0.470100 1.126137 0.557714 0.170 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
Sb1 0.04167(19) 0.04006(19) 0.0500(2) 0.0061(2) 0.0023(2) 0.0027(2)
I2 0.0767(3) 0.0538(3) 0.0910(4) 0.0056(3) 0.0234(3) -0.0194(3)
I1 0.0766(3) 0.0906(4) 0.0557(3) -0.0252(3) 0.0016(3) -0.0114(3)
I3 0.0789(3) 0.0713(3) 0.0829(4) 0.0244(3) -0.0109(3) 0.0248(3)
I5 0.0623(3) 0.0676(3) 0.1025(4) 0.0126(3) 0.0128(3) -0.0200(3)
I4 0.0778(3) 0.0839(4) 0.0639(3) -0.0293(3) 0.0038(3) 0.0052(3)
N1 0.142(3) 0.142(3) 0.143(3) 0.003(3) 0.001(3) 0.004(3)
C2 0.132(3) 0.130(3) 0.134(3) -0.001(3) 0.000(3) -0.003(3)
C3 0.137(3) 0.128(3) 0.139(3) 0.006(3) 0.000(3) 0.004(3)
N2 0.143(3) 0.143(3) 0.143(3) 0.003(3) -0.003(3) 0.002(3)
C1 0.144(3) 0.144(3) 0.146(3) 0.000(3) 0.000(3) 0.005(3)
C4 0.137(3) 0.122(3) 0.131(3) 0.003(3) -0.001(3) 0.004(3)
N3 0.159(7) 0.171(7) 0.184(7) -0.035(6) -0.045(6) -0.021(6)
C5 0.146(4) 0.132(4) 0.146(4) -0.005(4) -0.005(4) 0.000(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
Sb1 I2 2.8952(8) . ?
Sb1 I1 3.0008(8) . ?
Sb1 I3 2.8604(8) . ?
Sb1 I5 3.1750(8) . ?
Sb1 I5 3.2270(8) 2_466 ?
Sb1 I4 3.0371(8) . ?
N1 H1 0.8600 . ?
N1 C2 1.4200 . ?
N1 C1 1.4200 . ?
C2 H2 0.9300 . ?
C2 C3 1.4200 . ?
C3 N2 1.4200 . ?
C3 C4 1.446(11) . ?
N2 H2A 0.8600 . ?
N2 C1 1.4200 . ?
C1 H1A 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.435(12) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N3 C5 1.456(12) . ?
C5 H5A 0.9700 . ?
C5 H5B 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
I2 Sb1 I1 90.27(2) . . ?
I2 Sb1 I5 176.75(3) . . ?
I2 Sb1 I5 88.83(2) . 2_466 ?
I2 Sb1 I4 89.52(2) . . ?
I1 Sb1 I5 87.51(2) . 2_466 ?
I1 Sb1 I5 91.53(2) . . ?
I1 Sb1 I4 176.42(3) . . ?
I3 Sb1 I2 94.64(2) . . ?
I3 Sb1 I1 92.42(2) . . ?
I3 Sb1 I5 176.53(3) . 2_466 ?
I3 Sb1 I5 87.98(2) . . ?
I3 Sb1 I4 91.16(2) . . ?
I5 Sb1 I5 88.549(11) . 2_466 ?
I4 Sb1 I5 88.51(2) . . ?
I4 Sb1 I5 88.91(2) . 2_466 ?
Sb1 I5 Sb1 176.71(3) . 2_566 ?
C2 N1 H1 126.0 . . ?
C2 N1 C1 108.0 . . ?
C1 N1 H1 126.0 . . ?
N1 C2 H2 126.0 . . ?
N1 C2 C3 108.0 . . ?
C3 C2 H2 126.0 . . ?
C2 C3 N2 108.0 . . ?
C2 C3 C4 136.9(9) . . ?
N2 C3 C4 115.0(9) . . ?
C3 N2 H2A 126.0 . . ?
C1 N2 C3 108.0 . . ?
C1 N2 H2A 126.0 . . ?
N1 C1 H1A 126.0 . . ?
N2 C1 N1 108.0 . . ?
N2 C1 H1A 126.0 . . ?
C3 C4 H4A 100.6 . . ?
C3 C4 H4B 100.6 . . ?
H4A C4 H4B 104.3 . . ?
C5 C4 C3 145.1(11) . . ?
C5 C4 H4A 100.6 . . ?
C5 C4 H4B 100.6 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C5 N3 H3A 109.5 . . ?
C5 N3 H3B 109.5 . . ?
C5 N3 H3C 109.5 . . ?
C4 C5 N3 90.4(9) . . ?
C4 C5 H5A 113.6 . . ?
C4 C5 H5B 113.6 . . ?
N3 C5 H5A 113.6 . . ?
N3 C5 H5B 113.6 . . ?
H5A C5 H5B 110.8 . . ?

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
N1 C2 C3 N2 0.0 . . . . ?
N1 C2 C3 C4 -175.3(13) . . . . ?
C2 N1 C1 N2 0.0 . . . . ?
C2 C3 N2 C1 0.0 . . . . ?
C2 C3 C4 C5 66(3) . . . . ?
C3 N2 C1 N1 0.0 . . . . ?
C3 C4 C5 N3 -26(2) . . . . ?
N2 C3 C4 C5 -109(2) . . . . ?
C1 N1 C2 C3 0.0 . . . . ?
C4 C3 N2 C1 176.5(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
