# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Structure_I
_database_code_depnum_ccdc_archive 'CCDC 1580940'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1,3-dimethyl-2-oxo-2,3-dihydropyrimidinium iodoantimonate'
_chemical_formula_moiety         'Sb I4, (C6 H9 N2 O)'
_chemical_formula_sum            'C6 H9 I4 N2 O Sb'
_chemical_formula_weight         754.52

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'
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'
I I -0.4742 1.8119 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.5506(4)
_cell_length_b                   7.6199(3)
_cell_length_c                   19.9962(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.336(3)
_cell_angle_gamma                90
_cell_volume                     1600.63(10)
_cell_formula_units_Z            4.00
_cell_measurement_temperature    149.9(4)
_cell_measurement_reflns_used    3491
_cell_measurement_theta_min      3.7870
_cell_measurement_theta_max      31.1860
_cell_oxdiff_length_a            10.5721(7)
_cell_oxdiff_length_b            7.6064(4)
_cell_oxdiff_length_c            19.9946(9)
_cell_oxdiff_angle_alpha         90.037(4)
_cell_oxdiff_angle_beta          95.441(5)
_cell_oxdiff_angle_gamma         90.004(5)
_cell_oxdiff_volume              1600.63(16)
_cell_oxdiff_measurement_reflns_used 3491

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    3.131
_exptl_crystal_F_000             1320.0
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.034
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -11 0 0.1515
0 11 1 0.1509
3 0 -28 0.0444
-3 0 28 0.0347
-15 0 -3 0.0285
15 0 3 0.0057
-6 0 -24 0.0384
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.2271 -10.7222 0.2084 0.1076 0.0706 0.9917
-0.3758 10.7108 1.2395 -0.1496 -0.0996 -0.9837
2.8779 0.3077 -28.0390 0.8123 0.5602 -0.1621
-2.8802 -0.2322 28.0435 -0.8133 -0.5608 0.1552
-14.6217 -0.3057 -2.7631 0.5673 -0.8235 0.0092
14.6217 0.3057 2.7631 -0.5673 0.8235 -0.0092
-6.1730 0.2072 -24.4299 0.9900 -0.0244 -0.1390

_exptl_absorpt_coefficient_mu    9.418
_exptl_absorpt_correction_T_min  0.144
_exptl_absorpt_correction_T_max  0.621
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.661
_oxdiff_exptl_absorpt_empirical_full_max 1.286
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      149.9(4)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            9685
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.367
_diffrn_reflns_theta_max         31.825
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0324310000
_diffrn_orient_matrix_UB_12      -0.0113497000
_diffrn_orient_matrix_UB_13      -0.0324252000
_diffrn_orient_matrix_UB_21      0.0590780000
_diffrn_orient_matrix_UB_22      -0.0056063000
_diffrn_orient_matrix_UB_23      -0.0139768000
_diffrn_orient_matrix_UB_31      0.0003907000
_diffrn_orient_matrix_UB_32      -0.0923873000
_diffrn_orient_matrix_UB_33      0.0048082000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00 -11.00   1.00   19.17    --   23.53 -77.00 -60.00   32
  2  ω      0.00  50.00   1.00   19.17    --   23.53 -77.00 -60.00   50
  3  ω     42.00  80.00   1.00   19.17    --   23.53  38.00-180.00   38
  4  ω    -42.00   9.00   1.00   19.17    --   23.53 -77.00-150.00   51
  5  ω     -3.00  91.00   1.00   19.17    --   23.53  77.00  60.00   94
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_reflns_odcompleteness_completeness 97.21
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             4798
_reflns_number_gt                3774
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Palmer, D. C. (2014). CrystalMaker. CrystalMaker Software Ltd, Begbroke, Oxfordshire, England.'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0185P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4798
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0768
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_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
N1 N 0.1167(5) -0.6493(6) 0.1660(2) 0.0188(11) Uani 1 1 d . . . . .
O1 O 0.0025(5) -0.4628(7) 0.2262(2) 0.0395(13) Uani 1 1 d . . . . .
N2 N 0.1502(5) -0.6376(6) 0.2829(2) 0.0211(11) Uani 1 1 d . . . . .
C2 C 0.0820(6) -0.5744(9) 0.2255(3) 0.0236(14) Uani 1 1 d . . . . .
C6 C 0.2092(6) -0.7672(8) 0.1652(3) 0.0263(14) Uani 1 1 d . . . . .
H6 H 0.2305 -0.8098 0.1241 0.032 Uiso 1 1 calc R U . . .
C1 C 0.0443(7) -0.5838(10) 0.1040(3) 0.041(2) Uani 1 1 d . . . . .
H1A H -0.0179 -0.4998 0.1156 0.062 Uiso 1 1 calc R U . . .
H1B H 0.1016 -0.5289 0.0758 0.062 Uiso 1 1 calc R U . . .
H1C H 0.0021 -0.6802 0.0804 0.062 Uiso 1 1 calc R U . . .
C5 C 0.2738(6) -0.8276(8) 0.2229(3) 0.0261(14) Uani 1 1 d . . . . .
H5 H 0.3380 -0.9112 0.2222 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2397(6) -0.7593(8) 0.2819(3) 0.0246(14) Uani 1 1 d . . . . .
H4 H 0.2803 -0.7993 0.3223 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1122(7) -0.5644(10) 0.3464(3) 0.0373(19) Uani 1 1 d . . . . .
H3A H 0.0464 -0.4786 0.3367 0.056 Uiso 1 1 calc R U . . .
H3B H 0.0809 -0.6570 0.3730 0.056 Uiso 1 1 calc R U . . .
H3C H 0.1845 -0.5101 0.3708 0.056 Uiso 1 1 calc R U . . .
I1 I 0.53794(4) 0.07734(5) 0.10424(2) 0.02103(10) Uani 1 1 d . . . . .
I2 I 0.30766(4) -0.57714(5) -0.02849(2) 0.02309(10) Uani 1 1 d . . . . .
Sb1 Sb 0.41463(4) -0.24430(5) 0.04234(2) 0.01646(9) Uani 1 1 d . . . . .
I4 I 0.16223(4) -0.10513(5) 0.02800(2) 0.02183(10) Uani 1 1 d . . . . .
I3 I 0.39639(5) -0.37034(6) 0.17468(2) 0.03103(12) Uani 1 1 d . . . . .


_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 C6 1.327(8) . ?
N1 C2 1.399(7) . ?
N1 C1 1.481(7) . ?
O1 C2 1.195(7) . ?
N2 C4 1.325(8) . ?
N2 C2 1.382(7) . ?
N2 C3 1.476(7) . ?
C6 C5 1.366(8) . ?
C5 C4 1.367(8) . ?
I1 Sb1 2.9887(5) . ?
I2 Sb1 3.0683(5) . ?
Sb1 I3 2.8386(5) . ?
Sb1 I4 2.8559(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
C6 N1 C2 122.5(5) . . ?
C6 N1 C1 122.7(5) . . ?
C2 N1 C1 114.8(5) . . ?
C4 N2 C2 123.2(5) . . ?
C4 N2 C3 121.9(5) . . ?
C2 N2 C3 114.8(5) . . ?
O1 C2 N2 123.3(6) . . ?
O1 C2 N1 122.6(5) . . ?
N2 C2 N1 114.0(5) . . ?
N1 C6 C5 121.9(6) . . ?
C6 C5 C4 116.7(6) . . ?
N2 C4 C5 121.7(6) . . ?
I3 Sb1 I4 94.348(18) . . ?
I3 Sb1 I1 87.476(15) . . ?
I4 Sb1 I1 95.912(16) . . ?
I3 Sb1 I2 95.553(16) . . ?
I4 Sb1 I2 87.768(15) . . ?
I1 Sb1 I2 175.057(19) . . ?

_refine_diff_density_max         1.374
_refine_diff_density_min         -1.034
_refine_diff_density_rms         0.248


# start Validation Reply Form
_vrf_PLAT342_Structure_I         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.009 Ang.  
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher
;
_vrf_PLAT790_Structure_I         
;
PROBLEM: Centre of Gravity not Within Unit Cell: Resd.  #          1 Note  
RESPONSE: Connected set organic residue resolved within the asymmetric unit cell alongside anionic SbI4 component
;
# end Validation Reply Form

####################################################################### 
# 
# 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_Structure_IX
_database_code_depnum_ccdc_archive 'CCDC 1580948'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT780_Structure_IX        
;
PROBLEM: Coordinates do not Form a Properly Connected Set     Please Do !
RESPONSE: High level of distortion within the Sb4I16 structural unit has resulted in a disconnected set for the anionic substructure
;
# Added during the CSD deposition process: Wednesday 20 December 2017 04:32 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1,4-dimethyl-1,4-dipiperazinium iodoantimonate dihydrate'
_chemical_formula_iupac          '[CH3NH(CH2)4NHCH3]2[Sb4I16].2H2O'
_chemical_formula_moiety         'Sb4 I16, 2(C6 N2 H16), 2(H2O)'
_chemical_formula_sum            'C6 H18 I8 N2 O Sb2'
_chemical_formula_weight         1392.94

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.5391(3)
_cell_length_b                   11.8717(4)
_cell_length_c                   19.1648(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.705(3)
_cell_angle_gamma                90
_cell_volume                     2619.87(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    7221
_cell_measurement_theta_min      3.9380
_cell_measurement_theta_max      31.6540
_cell_oxdiff_length_b            11.8768(5)
_cell_oxdiff_length_c            19.1657(6)
_cell_oxdiff_angle_alpha         90.003(3)
_cell_oxdiff_angle_beta          93.721(4)
_cell_oxdiff_angle_gamma         89.970(4)
_cell_oxdiff_volume              2619.9(2)
_cell_oxdiff_measurement_reflns_used 7221

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    3.531
_exptl_crystal_F_000             2408
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.193
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-13 -1 -16 0.1715
10 12 -9 0.0841
13 3 13 0.1422
5 13 -16 0.0854
-2 -6 -25 0.1358
-13 10 3 0.1065
3 6 25 0.1063
11 -2 19 0.1406
-8 -13 11 0.1159
-13 -10 0 0.1115
0 11 -20 0.0959
7 -6 21 0.1245
6 -13 12 0.1076
-2 -17 0 0.1027
4 -15 9 0.1021
-5 -15 -7 0.1010
8 -14 3 0.1154
3 -16 -9 0.1197
-2 -13 -16 0.1071
7 -2 23 0.1227
3 0 -27 0.1208
12 -1 -19 0.1445
16 -2 -3 0.1416
12 6 -17 0.1084
8 14 4 0.1055
0 16 -10 0.0826
-10 1 22 0.0881
-15 2 12 0.0829
-14 -4 13 0.0885
1 3 26 0.1051
7 15 -7 0.0760
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-12.5155 -0.8785 -15.8077 -0.2094 -0.0360 -0.9772
9.8860 12.4635 -8.5395 0.9757 0.1816 0.1223
13.3830 3.1030 13.0382 0.3729 0.0666 0.9255
5.2023 12.8040 -15.6508 0.9435 0.1768 -0.2804
-2.2916 -5.9020 -24.6989 0.1226 -0.6681 -0.7339
-13.1328 9.8178 3.0019 -0.1529 0.8117 -0.5637
2.7467 5.5955 24.7066 -0.1179 0.6436 0.7562
10.8942 -1.7651 18.6386 0.0018 0.0050 1.0000
-8.3390 -12.8308 11.3510 -0.9828 -0.1832 0.0250
-12.8217 -10.2883 0.4340 -0.8584 -0.1617 -0.4868
-0.3632 10.9801 -20.3089 0.7550 0.1387 -0.6409
7.0760 -6.2742 21.3088 -0.3526 -0.0627 0.9337
5.8842 -13.4659 12.0706 -0.5075 -0.5326 0.6774
-1.5096 -16.6728 0.0798 -0.6870 -0.7253 0.0457
3.5947 -15.3671 8.5009 -0.5999 -0.6311 0.4917
-5.4879 -15.0629 -6.8983 -0.6481 -0.6861 -0.3305
8.4898 -14.0646 3.0317 -0.2796 -0.7865 0.5507
2.9248 -15.6030 -8.8059 -0.3327 -0.9430 -0.0070
-1.8137 -13.4077 -15.6758 -0.3010 -0.8573 -0.4178
7.0204 -1.5092 23.4418 -0.2112 0.1955 0.9577
3.1675 0.2383 -26.7860 0.5877 -0.5537 -0.5900
12.4070 -1.1888 -18.6608 0.7252 -0.6869 0.0487
16.1229 -2.0736 -2.7596 0.5495 -0.5234 0.6512
12.1527 5.6616 -16.7389 0.9420 -0.3326 0.0445
8.4851 13.8916 4.4695 0.7537 0.5178 0.4047
-0.0861 15.5091 -10.1545 0.7602 0.5251 -0.3825
-10.2701 0.8383 21.9686 -0.7189 0.6813 0.1380
-14.8619 1.6379 12.2186 -0.6847 0.6470 -0.3354
-14.2704 -3.5098 13.1708 -0.8749 0.4153 -0.2493
1.4738 2.5957 26.3665 -0.3061 0.5667 0.7650
6.7734 14.7056 -7.0862 0.9234 0.3837 0.0094

_exptl_absorpt_coefficient_mu    11.486
_exptl_absorpt_correction_T_min  0.039
_exptl_absorpt_correction_T_max  0.119
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.887
_oxdiff_exptl_absorpt_empirical_full_max 1.137
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            17079
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.332
_diffrn_reflns_theta_max         32.030
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0359831000
_diffrn_orient_matrix_UB_12      0.0378610000
_diffrn_orient_matrix_UB_13      -0.0173476000
_diffrn_orient_matrix_UB_21      -0.0234506000
_diffrn_orient_matrix_UB_22      0.0457105000
_diffrn_orient_matrix_UB_23      0.0183040000
_diffrn_orient_matrix_UB_31      0.0441949000
_diffrn_orient_matrix_UB_32      -0.0066141000
_diffrn_orient_matrix_UB_33      0.0271932000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00 -35.00   1.00    7.50    --  -22.90-178.00  30.00   45
  2  ω    -90.00 -60.00   1.00    7.50    --  -22.90 -57.00 -90.00   30
  3  ω    -87.00   3.00   1.00    7.50    --  -22.90 -77.00 -30.00   90
  4  ω    -21.00  48.00   1.00    7.50    --   23.53 -77.00-150.00   69
  5  ω     34.00  62.00   1.00    7.50    --   23.53 -99.00  90.00   28
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             8103
_reflns_number_gt                6747
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Palmer, D. C. (2014). CrystalMaker. CrystalMaker Software Ltd, Begbroke, Oxfordshire, England.'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0085P)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       0.000665(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8103
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0578
_refine_ls_wR_factor_gt          0.0544
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
N1 N 0.5930(4) 0.7251(4) 0.3392(2) 0.0265(11) Uani 1 1 d . . . . .
H1 H 0.6481 0.7249 0.3024 0.032 Uiso 1 1 calc R U . . .
O1 O 0.7970(4) 0.6753(5) 0.2729(2) 0.0503(14) Uani 1 1 d G . . . .
H1O1 H 0.8199 0.6598 0.2322 0.09(3) Uiso 1 1 d G . . . .
H2O1 H 0.8486 0.6466 0.3023 0.10(4) Uiso 1 1 d G . . . .
N2 N 0.4755(4) 0.5138(4) 0.3072(2) 0.0211(10) Uani 1 1 d . . . . .
H2 H 0.4192 0.5146 0.3434 0.025 Uiso 1 1 calc R U . . .
C4 C 0.5948(5) 0.5176(5) 0.3424(3) 0.0287(13) Uani 1 1 d . . . . .
H4A H 0.6057 0.4532 0.3733 0.034 Uiso 1 1 calc R U . . .
H4B H 0.6517 0.5128 0.3074 0.034 Uiso 1 1 calc R U . . .
C2 C 0.4545(5) 0.6141(5) 0.2623(3) 0.0263(13) Uani 1 1 d . . . . .
H2A H 0.3758 0.6123 0.2413 0.032 Uiso 1 1 calc R U . . .
H2B H 0.5076 0.6138 0.2251 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6142(5) 0.6232(5) 0.3836(3) 0.0272(13) Uani 1 1 d . . . . .
H3A H 0.5626 0.6244 0.4216 0.033 Uiso 1 1 calc R U . . .
H3B H 0.6934 0.6246 0.4038 0.033 Uiso 1 1 calc R U . . .
C1 C 0.4724(5) 0.7197(5) 0.3056(3) 0.0265(13) Uani 1 1 d . . . . .
H1A H 0.4584 0.7852 0.2759 0.032 Uiso 1 1 calc R U . . .
H1B H 0.4169 0.7212 0.3415 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4574(6) 0.4082(5) 0.2651(3) 0.0320(14) Uani 1 1 d . . . . .
H5A H 0.4713 0.3439 0.2949 0.048 Uiso 1 1 calc R U . . .
H5B H 0.3790 0.4060 0.2450 0.048 Uiso 1 1 calc R U . . .
H5C H 0.5103 0.4070 0.2284 0.048 Uiso 1 1 calc R U . . .
C6 C 0.6105(7) 0.8312(5) 0.3816(4) 0.0485(19) Uani 1 1 d . . . . .
H6A H 0.5963 0.8955 0.3519 0.073 Uiso 1 1 calc R U . . .
H6B H 0.5575 0.8321 0.4182 0.073 Uiso 1 1 calc R U . . .
H6C H 0.6888 0.8338 0.4017 0.073 Uiso 1 1 calc R U . . .
I1 I 0.18138(3) 1.06132(3) 0.03609(2) 0.01741(7) Uani 1 1 d . . . . .
I2 I 0.45585(3) 0.82429(3) -0.04878(2) 0.01717(7) Uani 1 1 d . . . . .
Sb1 Sb 0.40477(3) 0.95260(3) 0.09707(2) 0.01271(7) Uani 1 1 d . . . . .
Sb2 Sb 0.79527(3) 1.19628(3) 0.47558(2) 0.01557(8) Uani 1 1 d . . . . .
I4 I 0.62801(3) 0.85857(3) 0.16031(2) 0.01790(8) Uani 1 1 d . . . . .
I5 I 0.37689(3) 1.06092(3) 0.22809(2) 0.02466(9) Uani 1 1 d . . . . .
I3 I 0.26975(3) 0.76257(3) 0.12639(2) 0.02530(9) Uani 1 1 d . . . . .
I6 I 0.76134(4) 0.57814(3) -0.09396(2) 0.02872(9) Uani 1 1 d . . . . .
I7 I 0.57407(3) 1.16797(3) 0.40731(2) 0.02722(9) Uani 1 1 d . . . . .
I8 I 0.89369(4) 1.01397(3) 0.41028(2) 0.02972(10) Uani 1 1 d . . . . .


_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 C3 1.490(7) . ?
N1 C1 1.497(7) . ?
N1 C6 1.506(7) . ?
N2 C2 1.479(6) . ?
N2 C4 1.495(7) . ?
N2 C5 1.498(7) . ?
C4 C3 1.491(8) . ?
C2 C1 1.510(8) . ?
I1 Sb1 3.0474(5) . ?
Sb1 I3 2.8188(5) . ?
Sb1 I5 2.8577(5) . ?
Sb1 I4 2.9912(5) . ?
Sb2 I8 2.7791(5) . ?
Sb2 I6 2.7807(5) 2_655 ?
Sb2 I7 2.8120(5) . ?
I6 Sb2 2.7807(5) 2_645 ?

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
C3 N1 C1 109.0(4) . . ?
C3 N1 C6 111.1(4) . . ?
C1 N1 C6 110.9(5) . . ?
C2 N2 C4 110.4(4) . . ?
C2 N2 C5 110.5(4) . . ?
C4 N2 C5 111.1(4) . . ?
C3 C4 N2 111.5(5) . . ?
N2 C2 C1 109.8(4) . . ?
N1 C3 C4 111.5(4) . . ?
N1 C1 C2 111.2(5) . . ?
I3 Sb1 I5 95.159(14) . . ?
I3 Sb1 I4 95.344(14) . . ?
I5 Sb1 I4 87.410(13) . . ?
I3 Sb1 I1 87.173(13) . . ?
I5 Sb1 I1 90.339(13) . . ?
I4 Sb1 I1 176.762(15) . . ?
I8 Sb2 I6 95.678(15) . 2_655 ?
I8 Sb2 I7 94.731(16) . . ?
I6 Sb2 I7 93.745(16) 2_655 . ?

_refine_diff_density_max         1.217
_refine_diff_density_min         -1.248
_refine_diff_density_rms         0.233

####################################################################### 
# 
# 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_Structure_III
_database_code_depnum_ccdc_archive 'CCDC 1580942'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_Structure_III       
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         16 Note
RESPONSE: Relatively small number of missing FCF reflections likely due to omissions from initial data reduction
;
_vrf_PLAT230_Structure_III       
;
PROBLEM: Hirshfeld Test Diff for   O1       --C3        .        6.0 s.u.
RESPONSE: Discrepancies may occur in the organic component here due to polarisat
;
_vrf_PLAT342_Structure_III       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0085 Ang.
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will b
;
# Added during the CSD deposition process: Wednesday 20 December 2017 01:29 PM
# end Validation Reply Form


_audit_creation_method           'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-methylmorpholinium iodoantimonate'
_chemical_formula_moiety         'Sb6 I22, 4(C5 N O H12)'
_chemical_formula_sum            'C10 H24 I11 N2 O2 Sb3'
_chemical_formula_weight         1965.49

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   11.3253(7)
_cell_length_b                   13.0042(7)
_cell_length_c                   15.2847(7)
_cell_angle_alpha                69.645(4)
_cell_angle_beta                 69.877(5)
_cell_angle_gamma                64.496(6)
_cell_volume                     1853.97(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    9168
_cell_measurement_theta_min      3.7740
_cell_measurement_theta_max      31.7090
_cell_oxdiff_length_a            11.3253(7)
_cell_oxdiff_length_b            13.0042(7)
_cell_oxdiff_length_c            15.2847(6)
_cell_oxdiff_angle_alpha         69.645(4)
_cell_oxdiff_angle_beta          69.877(5)
_cell_oxdiff_angle_gamma         64.496(6)
_cell_oxdiff_volume              1853.97(17)
_cell_oxdiff_measurement_reflns_used 9168

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.175
_exptl_crystal_density_diffrn    3.521
_exptl_crystal_F_000             1700
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
13 0 12 0.1146
14 11 -1 0.1343
0 11 -12 0.0976
-15 -10 -2 0.2165
0 -10 12 0.1314
7 -8 -12 0.0955
-1 12 16 0.0481
11 15 16 0.1092
-14 -2 2 0.1849
-15 -2 -10 0.1997
15 4 1 0.1392
4 -10 -14 0.0890
-14 -14 -14 0.2213
2 17 0 0.0903
11 -6 4 0.1236
1 -16 1 0.1388
-11 -16 -3 0.2150
4 -13 -8 0.1100
4 4 21 0.0879
12 8 19 0.1107
-10 -7 -21 0.1975
-2 2 19 0.1014
3 -3 19 0.1027
-1 15 -3 0.0836
0 -1 -20 0.0881
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
13.1124 -0.2739 11.9785 -0.4632 0.4416 0.7684
13.6681 11.3165 -0.9408 0.3157 -0.2954 0.9017
0.2701 10.6241 -12.0551 0.7221 -0.6833 0.1082
-15.2767 -9.5845 -2.4942 -0.1419 0.1306 -0.9812
0.4426 -10.3125 12.3283 -0.7248 0.6860 -0.0636
6.9948 -7.5143 -11.8487 -0.5906 -0.6258 0.5094
-1.1190 12.0518 15.7772 0.6796 0.7183 -0.1488
11.2629 15.2402 15.9012 0.5234 0.5501 0.6507
-14.1128 -2.0128 1.9332 0.2654 0.2841 -0.9213
-14.6400 -2.1589 -10.3502 0.3465 -0.3240 -0.8803
15.1058 4.3702 0.9226 -0.1656 -0.1700 0.9714
4.3746 -9.8035 -13.8841 -0.6450 -0.6794 0.3499
-13.7060 -14.0261 -13.6993 -0.3924 -0.4185 -0.8191
2.0476 16.8353 0.3381 0.9793 -0.1283 0.1566
11.4118 -5.8355 3.7572 -0.7080 0.0902 0.7004
0.9408 -15.5576 0.5931 -0.9911 0.1293 0.0316
-11.2831 -16.4773 -3.2968 -0.6763 0.0906 -0.7310
4.2593 -13.0934 -8.1395 -0.8800 -0.3666 0.3021
3.7457 4.2464 21.3311 0.0252 0.9928 0.1170
11.6363 7.6042 19.2200 0.0210 0.7664 0.6420
-9.6929 -6.8708 -20.5288 -0.0230 -0.8610 -0.5081
-1.5657 1.5784 19.3192 0.0239 0.9761 -0.2161
2.5626 -3.1846 18.5811 -0.3832 0.9225 0.0459
-1.1288 14.9468 -2.7830 0.9721 -0.2324 -0.0313
0.2918 -0.5488 -19.7074 0.0783 -0.9873 0.1383
_exptl_absorpt_coefficient_mu    11.340
_exptl_absorpt_correction_T_min  0.048
_exptl_absorpt_correction_T_max  0.150
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.792
_oxdiff_exptl_absorpt_empirical_full_max 1.252
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.01(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            20186
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.433
_diffrn_reflns_theta_max         32.016
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0284525000
_diffrn_orient_matrix_UB_12      0.0617519000
_diffrn_orient_matrix_UB_13      -0.0061141000
_diffrn_orient_matrix_UB_21      -0.0122492000
_diffrn_orient_matrix_UB_22      -0.0071396000
_diffrn_orient_matrix_UB_23      0.0501149000
_diffrn_orient_matrix_UB_31      0.0642145000
_diffrn_orient_matrix_UB_32      0.0016157000
_diffrn_orient_matrix_UB_33      -0.0061116000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  42.00   1.00   10.00    --  -22.90  19.00  60.00   94
  2  ω     -1.00  91.00   1.00   10.00    --   23.53  77.00 120.00   92
  3  ω     -3.00  86.00   1.00   10.00    --   23.53  77.00 -60.00   89
  4  ω     36.00  69.00   1.00   10.00    --   23.53-120.00  54.00   33
  5  ω    -90.00 -35.00   1.00   10.00    --  -22.90 -19.00-150.00   55
  6  ω    -68.00  -9.00   1.00   10.00    --  -22.90 120.00 139.00   59
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P -1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             11292
_reflns_number_gt                9352
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Palmer, D. C. (2014). CrystalMaker. CrystalMaker Software Ltd, Begbroke, Oxfordshire, England.'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0063P)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       0.000991(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         11292
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0633
_refine_ls_wR_factor_gt          0.0596
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
I8 I 0.18948(3) 0.88747(3) 0.41207(2) 0.01749(7) Uani 1 1 d . . . . .
I5 I 0.01332(3) 0.72178(3) 0.69380(2) 0.01818(7) Uani 1 1 d . . . . .
I3 I -0.18754(4) 0.48932(4) 0.75650(3) 0.03244(10) Uani 1 1 d . . . . .
I1 I -0.54417(3) 0.68808(4) 0.90254(3) 0.03412(10) Uani 1 1 d . . . . .
I11 I 0.33541(3) 1.06380(4) 0.10713(3) 0.02283(8) Uani 1 1 d . . . . .
I2 I -0.18011(4) 0.56540(4) 0.98654(3) 0.03526(11) Uani 1 1 d . . . . .
I9 I 0.12837(4) 0.85128(4) 0.15095(3) 0.02701(9) Uani 1 1 d . . . . .
I7 I -0.20864(3) 1.02483(3) 0.34200(2) 0.01957(8) Uani 1 1 d . . . . .
I6 I -0.01930(3) 0.66440(3) 0.45404(3) 0.02466(8) Uani 1 1 d . . . . .
I10 I -0.06939(3) 1.21383(3) 0.07912(2) 0.02204(8) Uani 1 1 d . . . . .
Sb2 Sb -0.10051(3) 0.86665(3) 0.51731(2) 0.01477(7) Uani 1 1 d . . . . .
Sb1 Sb -0.28276(3) 0.69065(3) 0.82533(3) 0.01847(8) Uani 1 1 d . . . . .
Sb3 Sb 0.07312(3) 1.04838(3) 0.21560(2) 0.01584(7) Uani 1 1 d . . . . .
I4 I -0.36810(3) 0.86003(4) 0.60919(3) 0.02348(8) Uani 1 1 d . . . . .
O1 O -0.4933(4) 0.3891(4) 1.4686(3) 0.0318(10) Uani 1 1 d . . . . .
N1 N -0.5225(4) 0.5188(5) 1.2777(3) 0.0255(11) Uani 1 1 d . . . . .
H1 H -0.5729 0.4800 1.2680 0.031 Uiso 1 1 calc R U . . .
C2 C -0.3907(5) 0.4261(6) 1.2979(4) 0.0329(15) Uani 1 1 d . . . . .
H2A H -0.3358 0.4622 1.3043 0.039 Uiso 1 1 calc R U . . .
H2B H -0.3420 0.3878 1.2451 0.039 Uiso 1 1 calc R U . . .
C3 C -0.4183(6) 0.3368(6) 1.3896(5) 0.0379(16) Uani 1 1 d . . . . .
H3A H -0.4677 0.2973 1.3809 0.045 Uiso 1 1 calc R U . . .
H3B H -0.3336 0.2785 1.4033 0.045 Uiso 1 1 calc R U . . .
C4 C -0.6031(5) 0.5687(5) 1.3642(4) 0.0272(13) Uani 1 1 d . . . . .
H4A H -0.5577 0.6108 1.3743 0.033 Uiso 1 1 calc R U . . .
H4B H -0.6907 0.6236 1.3537 0.033 Uiso 1 1 calc R U . . .
C1 C -0.5026(6) 0.6088(7) 1.1903(4) 0.046(2) Uani 1 1 d . . . . .
H1A H -0.4508 0.5725 1.1374 0.070 Uiso 1 1 calc R U . . .
H1B H -0.5883 0.6631 1.1777 0.070 Uiso 1 1 calc R U . . .
H1C H -0.4555 0.6499 1.1983 0.070 Uiso 1 1 calc R U . . .
C5 C -0.6194(5) 0.4719(6) 1.4512(4) 0.0325(15) Uani 1 1 d . . . . .
H5A H -0.6713 0.5050 1.5065 0.039 Uiso 1 1 calc R U . . .
H5B H -0.6687 0.4327 1.4420 0.039 Uiso 1 1 calc R U . . .
N2 N 0.7608(4) 0.8621(4) 0.2001(3) 0.0173(9) Uani 1 1 d . . . . .
H2 H 0.8165 0.8570 0.2394 0.021 Uiso 1 1 calc R U . . .
O2 O 0.6713(4) 0.6689(4) 0.3072(3) 0.0303(10) Uani 1 1 d . . . . .
C9 C 0.8175(6) 0.7513(5) 0.1701(4) 0.0251(12) Uani 1 1 d . . . . .
H9A H 0.9114 0.7366 0.1376 0.030 Uiso 1 1 calc R U . . .
H9B H 0.7702 0.7572 0.1253 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6210(5) 0.8783(5) 0.2612(4) 0.0280(13) Uani 1 1 d . . . . .
H7A H 0.5614 0.8914 0.2225 0.034 Uiso 1 1 calc R U . . .
H7B H 0.5880 0.9464 0.2873 0.034 Uiso 1 1 calc R U . . .
C10 C 0.8057(5) 0.6500(5) 0.2560(4) 0.0296(14) Uani 1 1 d . . . . .
H10A H 0.8416 0.5783 0.2344 0.036 Uiso 1 1 calc R U . . .
H10B H 0.8588 0.6405 0.2983 0.036 Uiso 1 1 calc R U . . .
C8 C 0.6218(6) 0.7711(6) 0.3416(4) 0.0319(15) Uani 1 1 d . . . . .
H8A H 0.6774 0.7613 0.3821 0.038 Uiso 1 1 calc R U . . .
H8B H 0.5311 0.7819 0.3803 0.038 Uiso 1 1 calc R U . . .
C6 C 0.7634(6) 0.9639(6) 0.1162(4) 0.0345(15) Uani 1 1 d . . . . .
H6A H 0.7257 1.0346 0.1384 0.052 Uiso 1 1 calc R U . . .
H6B H 0.8546 0.9531 0.0809 0.052 Uiso 1 1 calc R U . . .
H6C H 0.7116 0.9695 0.0754 0.052 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
I8 Sb2 3.2054(5) . ?
I5 Sb2 3.0420(5) . ?
I3 Sb1 2.7980(6) . ?
I1 Sb1 2.7950(5) . ?
I11 Sb3 2.9164(5) . ?
I2 Sb1 2.7612(5) . ?
I9 Sb3 2.8095(5) . ?
I7 Sb2 3.0275(5) . ?
I7 Sb3 3.1933(5) . ?
I6 Sb2 2.7880(5) . ?
I10 Sb3 2.7910(5) . ?
Sb2 I4 2.8941(5) . ?
O1 C5 1.417(7) . ?
O1 C3 1.418(7) . ?
N1 C1 1.463(7) . ?
N1 C4 1.503(7) . ?
N1 C2 1.512(7) . ?
C2 C3 1.514(8) . ?
C4 C5 1.501(8) . ?
N2 C9 1.469(7) . ?
N2 C6 1.491(7) . ?
N2 C7 1.502(6) . ?
O2 C10 1.407(6) . ?
O2 C8 1.415(7) . ?
C9 C10 1.518(7) . ?
C7 C8 1.502(8) . ?

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
Sb2 I7 Sb3 94.555(13) . . ?
I6 Sb2 I4 92.303(15) . . ?
I6 Sb2 I7 92.882(15) . . ?
I4 Sb2 I7 87.255(14) . . ?
I6 Sb2 I5 90.563(15) . . ?
I4 Sb2 I5 94.798(14) . . ?
I7 Sb2 I5 175.918(16) . . ?
I6 Sb2 I8 89.804(14) . . ?
I4 Sb2 I8 177.226(17) . . ?
I7 Sb2 I8 90.839(13) . . ?
I5 Sb2 I8 86.982(13) . . ?
I2 Sb1 I1 98.606(17) . . ?
I2 Sb1 I3 92.193(18) . . ?
I1 Sb1 I3 94.240(17) . . ?
I10 Sb3 I9 96.461(15) . . ?
I10 Sb3 I11 96.271(15) . . ?
I9 Sb3 I11 91.391(15) . . ?
I10 Sb3 I7 86.118(14) . . ?
I9 Sb3 I7 88.711(15) . . ?
I11 Sb3 I7 177.582(15) . . ?
C5 O1 C3 109.9(4) . . ?
C1 N1 C4 112.8(5) . . ?
C1 N1 C2 111.9(4) . . ?
C4 N1 C2 109.2(4) . . ?
N1 C2 C3 109.2(4) . . ?
O1 C3 C2 112.1(5) . . ?
C5 C4 N1 110.0(5) . . ?
O1 C5 C4 111.5(4) . . ?
C9 N2 C6 111.7(4) . . ?
C9 N2 C7 110.0(4) . . ?
C6 N2 C7 111.5(4) . . ?
C10 O2 C8 108.8(4) . . ?
N2 C9 C10 110.8(4) . . ?
N2 C7 C8 109.7(4) . . ?
O2 C10 C9 111.6(5) . . ?
O2 C8 C7 111.9(5) . . ?

_refine_diff_density_max         1.554
_refine_diff_density_min         -1.385
_refine_diff_density_rms         0.235

####################################################################### 
# 
# 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_Structure_VI
_database_code_depnum_ccdc_archive 'CCDC 1580945'
_audit_update_record             
;
2018-01-25 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT417_Structure_VI        
;
PROBLEM: Short Inter D-H..H-D     H1       ..H1D       ..       2.07 Ang.
RESPONSE: Hydrogen positions within structure are unlikely to be accurate due to disorder in the position of the organic cation and water oxygen sites within the channel modelled with partial occupancies in addition to nearby heavy atoms adding to the difficulty of modelling weak electron density hydrogen positions
;
_vrf_PLAT417_Structure_VI_2      
;
PROBLEM: Short Inter D-H..H-D     H1C      ..H0AD      ..       1.95 Ang.
RESPONSE: Hydrogen positions within structure are unlikely to be accurate due to disorder in the position of the organic cation and water oxygen sites within the channel modelled with partial occupancies in addition to nearby heavy atoms adding to the difficulty of modelling weak electron density hydrogen positions
;
_vrf_PLAT420_Structure_VI        
;
PROBLEM: D-H Without Acceptor      O1       --H1C       .     Please Check
RESPONSE: Hydrogen positions within structure are unlikely to be accurate due to disorder in the position of the organic cation and water oxygen sites within the channel modelled with partial occupancies in addition to nearby heavy atoms adding to the difficulty of modelling weak electron density hydrogen positions
;
_vrf_PLAT420_Structure_VI_2      
;
PROBLEM: D-H Without Acceptor      O1       --H1D       .     Please Check
RESPONSE: Hydrogen positions within structure are unlikely to be accurate due to disorder in the position of the organic cation and water oxygen sites within the channel modelled with partial occupancies in addition to nearby heavy atoms adding to the difficulty of modelling weak electron density hydrogen positions
;
_vrf_PLAT245_Structure_VI        
;
PROBLEM: U(iso) H1C       Smaller than U(eq) O1        by      0.024 Ang**2
RESPONSE: Hydrogen positions within structure are unlikely to be accurate due to disorder in the position of the organic cation and water oxygen sites within the channel modelled with partial occupancies in addition to nearby heavy atoms adding to the difficulty of modelling weak electron density hydrogen positions
;
_vrf_PLAT245_Structure_VI_2      
;
PROBLEM: U(iso) H1D       Smaller than U(eq) O1        by      0.024 Ang**2
RESPONSE: Hydrogen positions within structure are unlikely to be accurate due to
;
_vrf_PLAT250_Structure_VI        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.5 Note
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher tied with disorder in the orientation/ conformation of the 1-methyldipiperazinium ring
;
_vrf_PLAT906_Structure_VI        
;
PROBLEM: Large K Value in the Analysis of Variance ......      3.908 Check
RESPONSE: Large K value due to the addition of hydrogen atoms modelled on disordered organic cation and water oxygen sites with split occupancy
;
_vrf_PLAT910_Structure_VI        
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          5 Note
RESPONSE: Relatively small number of missing FCF reflections likely due to omissions from initial data reduction
;
_vrf_PLAT971_Structure_VI        
;
PROBLEM: Check Calcd Resid. Dens.  0.78A   From I3              1.83 eA-3
RESPONSE: Residual electron density is in close proximity to heavy atom sublattice
;
_vrf_PLAT976_Structure_VI        
;
PROBLEM: Check Calcd Resid. Dens.  0.94A   From O1             -0.90 eA-3
RESPONSE: Disorder in modelling of attached hydrogen positions in disordered heavy atom containing hybrid structure
;
_vrf_PLAT977_Structure_VI        
;
PROBLEM: Check Negative Difference Density on H1               -0.51 eA-3
RESPONSE: Hydrogen modelled on nitrogen with a split occupancy disordered position and therefore shows some inaccuracy in electron density difference at the site
;
_vrf_PLAT977_Structure_VI_2      
;
PROBLEM: Check Negative Difference Density on H1C              -0.90 eA-3
RESPONSE: Hydrogen modelled on nitrogen with a split occupancy disordered position and therefore shows some inaccuracy in electron density difference at the site
;
_vrf_PLAT977_Structure_VI_3      
;
PROBLEM: Check Negative Difference Density on H1D              -0.60 eA-3
RESPONSE: Hydrogen modelled on nitrogen with a split occupancy disordered position and therefore shows some inaccuracy in electron density difference at the site
;
_vrf_PLAT977_Structure_VI_4      
;
PROBLEM: Check Negative Difference Density on H2D              -0.64 eA-3
RESPONSE: Hydrogen modelled on nitrogen with a split occupancy disordered position and therefore shows some inaccuracy in electron density difference at the site
;
# Added during the CSD deposition process: Thursday 25 January 2018 01:04 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1-methyl-1,4-dipiperazinium iodoantimonate trihydrate'
_chemical_formula_iupac          '[CH3NH(CH2)4NH2][SbI4]2.3H2O'
_chemical_formula_moiety         'Sb2 I8, (C5 N2 H14), 3(H2O)'
_chemical_formula_sum            'C2.50 H10 I4 N O1.50 Sb'
_chemical_formula_weight         707.46

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.5306(2)
_cell_length_b                   12.9539(4)
_cell_length_c                   13.6147(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.086(3)
_cell_angle_gamma                90
_cell_volume                     1320.64(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    3773
_cell_measurement_theta_min      4.1360
_cell_measurement_theta_max      31.4920
_cell_oxdiff_length_a            7.5242(5)
_cell_oxdiff_length_b            12.9620(10)
_cell_oxdiff_length_c            13.6180(7)
_cell_oxdiff_angle_alpha         90.047(5)
_cell_oxdiff_angle_beta          96.092(5)
_cell_oxdiff_angle_gamma         90.051(6)
_cell_oxdiff_volume              1320.64(15)
_cell_oxdiff_measurement_reflns_used 3773

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    3.558
_exptl_crystal_F_000             1228
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.137
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -13 9 0.1183
-2 -14 13 0.0766
-5 -11 12 0.1010
10 0 6 0.1606
5 9 14 0.1124
1 12 14 0.0896
-6 12 10 0.1520
8 8 -11 0.1183
1 14 -12 0.0512
-2 14 -11 0.0733
-8 10 -4 0.1460
7 14 0 0.1154
1 18 0 0.0563
0 18 0 0.0512
-6 15 0 0.1197
5 14 8 0.1005
1 17 8 0.0641
-2 17 7 0.0791
1 -1 19 0.0954
1 -9 16 0.0801
-10 -3 -3 0.1615
-5 -14 -6 0.1268
6 -15 -4 0.1049
7 -11 -11 0.0954
0 -11 -15 0.1188
-7 -4 -13 0.1407
-10 3 -4 0.1562
6 -5 -16 0.0749
1 10 -16 0.0660
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.9405 -13.0868 8.9990 0.4719 0.4953 0.7294
-2.0458 -13.5277 12.6981 0.6817 0.7194 0.1332
-5.3089 -11.4406 12.4381 0.6736 0.7122 -0.1979
9.5647 -0.3391 6.4116 0.3096 -0.2974 0.9031
4.5158 8.9738 13.6287 0.6847 -0.6498 0.3301
0.5389 11.9700 14.2768 0.7242 -0.6854 -0.0755
-6.4111 12.1772 9.5724 0.4969 -0.4671 -0.7314
7.9705 8.0859 -10.8729 -0.5945 -0.6254 0.5054
0.7898 13.9429 -12.4224 -0.6648 -0.7034 -0.2515
-2.1604 14.0959 -11.1138 -0.5898 -0.6254 -0.5108
-8.3413 9.7624 -4.3543 -0.2181 -0.2350 -0.9472
6.7066 14.0756 0.1943 -0.0247 -0.9349 0.3541
1.4010 18.1091 0.0578 -0.0239 -0.9808 -0.1938
-0.4532 18.2583 0.0087 -0.0221 -0.9315 -0.3630
-5.9955 15.0350 -0.1423 -0.0121 -0.5944 -0.8041
5.1983 13.5770 7.6790 0.3682 -0.8886 0.2735
0.5377 16.6453 7.6982 0.3767 -0.9048 -0.1985
-1.6345 16.8281 7.1421 0.3530 -0.8458 -0.4000
0.9960 -1.3506 18.7641 0.9733 -0.0251 0.2282
1.4906 -8.7705 16.2557 0.8515 0.3525 0.3882
-10.0944 -2.6585 -3.2183 -0.1387 0.4579 -0.8781
-5.4633 -14.1645 -5.9058 -0.2747 0.9210 -0.2761
5.5771 -15.3425 -3.7227 -0.1871 0.6364 0.7483
6.5514 -11.3191 -10.5139 -0.5473 0.4216 0.7230
0.4350 -10.8705 -15.3995 -0.7863 0.6025 0.1366
-6.8526 -4.3490 -12.5224 -0.6274 0.4781 -0.6146
-9.8864 3.3501 -4.0832 -0.1919 0.1434 -0.9709
5.9363 -4.6082 -16.2103 -0.8501 0.1126 0.5144
0.8606 9.6462 -16.3141 -0.8614 -0.4697 -0.1932

_exptl_absorpt_coefficient_mu    11.402
_exptl_absorpt_correction_T_min  0.027
_exptl_absorpt_correction_T_max  0.133
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.808
_oxdiff_exptl_absorpt_empirical_full_max 1.203
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.01(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            7436
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.357
_diffrn_reflns_theta_max         31.882
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4034
_reflns_number_gt                3401
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Palmer, D. C. (2014). CrystalMaker. CrystalMaker Software Ltd, Begbroke, Oxfordshire, England.'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0201P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00146(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4034
_refine_ls_number_parameters     129
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.026
_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_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 0.26499(4) 0.01819(3) 0.09048(2) 0.01533(9) Uani 1 1 d . . . . .
I1 I 0.13843(5) 0.18155(3) 0.20195(3) 0.02529(10) Uani 1 1 d . . . . .
I2 I -0.05519(5) -0.11456(3) 0.10649(2) 0.02129(10) Uani 1 1 d . . . . .
I3 I 0.43820(5) -0.08660(4) 0.25903(3) 0.02985(11) Uani 1 1 d . . . . .
I4 I 0.59028(4) 0.15107(3) 0.06160(3) 0.02098(9) Uani 1 1 d . . . . .
C0AA C 0.971(3) -0.027(2) 0.3990(19) 0.023(2) Uani 0.5 1 d . U P A -1
H0AA H 0.9080 -0.0742 0.3528 0.027 Uiso 0.5 1 calc R U P A -1
H0AB H 1.0351 0.0218 0.3613 0.027 Uiso 0.5 1 calc R U P A -1
C2 C 0.936(2) 0.0950(19) 0.5366(16) 0.029(3) Uani 0.5 1 d . U P A -1
H2A H 0.8543 0.1300 0.5757 0.034 Uiso 0.5 1 calc R U P A -1
H2B H 1.0074 0.1471 0.5077 0.034 Uiso 0.5 1 calc R U P A -1
C3 C 1.2270(19) -0.1324(12) 0.6321(10) 0.045(3) Uani 0.5 1 d . U P A -1
H3A H 1.3317 -0.1165 0.6005 0.068 Uiso 0.5 1 calc R U P A -1
H3B H 1.2133 -0.2059 0.6358 0.068 Uiso 0.5 1 calc R U P A -1
H3C H 1.2390 -0.1039 0.6976 0.068 Uiso 0.5 1 calc R U P A -1
O1 O 0.6606(9) -0.1281(5) 0.5412(4) 0.074(2) Uani 1 1 d . . . . .
H1C H 0.5846 -0.1199 0.4898 0.050 Uiso 1 1 d . . . . .
H1D H 0.6987 -0.1915 0.5363 0.050 Uiso 1 1 d . . . . .
N0AA N 0.8316(13) 0.0343(8) 0.4554(7) 0.0254(18) Uani 0.5 1 d . U P A -1
H0AC H 0.7675 0.0767 0.4141 0.030 Uiso 0.5 1 calc R U P A -1
H0AD H 0.7576 -0.0094 0.4808 0.030 Uiso 0.5 1 calc R U P A -1
O2 O 0.6456(13) 0.1644(7) 0.3339(6) 0.036(2) Uani 0.5 1 d . . P B -1
H2C H 0.6203 0.1407 0.2752 0.050 Uiso 0.5 1 d . . P C -1
H2D H 0.5680 0.2112 0.3416 0.050 Uiso 0.5 1 d . . P D -1
C1AA C 1.059(3) 0.025(2) 0.603(2) 0.032(3) Uani 0.5 1 d . U P A -1
H1AA H 1.1804 0.0498 0.6056 0.038 Uiso 0.5 1 calc R U P A -1
H1AB H 1.0237 0.0271 0.6697 0.038 Uiso 0.5 1 calc R U P A -1
C1 C 1.103(3) -0.086(2) 0.4669(16) 0.032(3) Uani 0.5 1 d . U P A -1
H1A H 1.1077 -0.1569 0.4449 0.038 Uiso 0.5 1 calc R U P A -1
H1B H 1.2214 -0.0561 0.4658 0.038 Uiso 0.5 1 calc R U P A -1
N1 N 1.0517(15) -0.0827(9) 0.5683(8) 0.0352(18) Uani 0.5 1 d . U P A -1
H1 H 0.9396 -0.1184 0.5766 0.042 Uiso 0.5 1 calc R U P A -1


_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 I1 2.8278(5) . ?
Sb1 I3 2.8593(5) . ?
Sb1 I2 2.9883(5) . ?
Sb1 I4 3.0532(5) . ?
Sb1 I2 3.2167(5) 3 ?
I2 Sb1 3.2167(5) 3 ?
C0AA C1 1.49(3) . ?
C0AA N0AA 1.58(3) . ?
C2 N0AA 1.51(2) . ?
C2 C1AA 1.52(3) . ?
C3 N1 1.633(16) . ?
C1AA N1 1.47(3) . ?
C1 N1 1.47(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
I1 Sb1 I3 94.334(15) . . ?
I1 Sb1 I2 94.072(14) . . ?
I3 Sb1 I2 88.349(15) . . ?
I1 Sb1 I4 88.159(15) . . ?
I3 Sb1 I4 93.844(14) . . ?
I2 Sb1 I4 176.750(15) . . ?
I1 Sb1 I2 89.618(14) . 3 ?
I3 Sb1 I2 174.420(18) . 3 ?
I2 Sb1 I2 87.441(13) . 3 ?
I4 Sb1 I2 90.214(13) . 3 ?
Sb1 I2 Sb1 92.560(13) . 3 ?
C1 C0AA N0AA 112.9(17) . . ?
N0AA C2 C1AA 111.1(18) . . ?
C2 N0AA C0AA 107.1(13) . . ?
N1 C1AA C2 112.0(18) . . ?
N1 C1 C0AA 109.9(15) . . ?
C1AA N1 C1 109.0(17) . . ?
C1AA N1 C3 101.7(12) . . ?
C1 N1 C3 102.0(11) . . ?

_refine_diff_density_max         1.829
_refine_diff_density_min         -1.207
_refine_diff_density_rms         0.268

####################################################################### 
# 
# 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_Structure_XIV
_database_code_depnum_ccdc_archive 'CCDC 1580953'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_Structure_XIV       
;
PROBLEM: D-H Without Acceptor      O1       --H1O1      .     Please Check
RESPONSE: Hydrogen positions only estimated in heavy atom containing structure therefore hydrogen-oxygen distances are not accurate
;
_vrf_PLAT342_Structure_XIV       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00967 Ang.
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will b
;
# Added during the CSD deposition process: Wednesday 20 December 2017 05:41 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1,4-diazabicyclo[2.2.2]octan-diium iodobismuthate dihydrate'
_chemical_formula_moiety         'Bi4 I16, 2(C6 N2 H14), 2(H2O)'
_chemical_formula_sum            'C12 H32 Bi4 I16 N4 O2'
_chemical_formula_weight         3130.03

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'
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'
Bi Bi -4.1077 10.2566 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.0086(3)
_cell_length_b                   15.4751(3)
_cell_length_c                   15.3455(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.001(2)
_cell_angle_gamma                90
_cell_volume                     2547.23(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    7217
_cell_measurement_theta_min      3.7570
_cell_measurement_theta_max      31.4020

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    4.082
_exptl_crystal_F_000             2656
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.215
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 10 15 0.1630
-13 7 -6 0.1569
0 -15 -15 0.1096
-9 -5 -13 0.1557
10 -16 -5 0.1499
12 -4 8 0.2034
13 3 6 0.1926
-1 -15 16 0.1275
-8 -16 12 0.0988
-13 -1 -8 0.1593
-12 -13 7 0.0986
15 0 2 0.1899
-6 -4 21 0.1322
-11 -4 18 0.1067
7 -7 -20 0.1156
15 -5 0 0.1802
-11 7 16 0.1100
-9 7 19 0.1065
-11 15 3 0.1167
-4 16 14 0.1454
10 12 8 0.1582
-7 18 -6 0.1239
0 22 -1 0.1683
-1 16 -15 0.1112
4 17 -13 0.1319
13 13 -2 0.1600
12 10 -13 0.1295
8 11 -17 0.1108
-3 8 -18 0.1292
10 -3 -19 0.1046
12 -13 -10 0.1267
8 -11 -17 0.1083
7 -18 -10 0.1306
-6 -20 1 0.1203
-9 -12 15 0.0931
-11 13 11 0.1090
2 9 19 0.1433
3 6 -21 0.1181
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.0166 10.0333 14.9540 -0.1858 0.6031 -0.7744
-12.9969 6.9704 -5.9394 -0.0791 0.2961 0.9662
-0.0213 -15.0250 -14.9797 0.2288 -0.8725 0.4072
-9.0111 -5.0345 -12.9446 0.1159 -0.3379 0.9054
9.9832 -15.9925 -5.0321 0.2433 -0.8155 -0.4858
12.0006 -3.9685 7.9407 0.0355 -0.1302 -0.9587
13.0038 3.0215 5.9244 -0.2789 -0.0121 -0.9304
-0.9984 -14.9489 16.0304 0.8884 0.0712 -0.4869
-8.0006 -15.9629 12.0701 1.0007 0.0723 0.0399
-13.0038 -1.0281 -7.9277 0.1662 0.0094 0.9990
-12.0013 -12.9805 7.0870 0.8813 0.0937 0.4371
14.9983 0.0154 1.9172 -0.2990 -0.2588 -0.9347
-5.9861 -3.9489 21.0424 0.7107 0.6386 -0.3101
-10.9873 -3.9598 18.0696 0.7625 0.6554 0.0732
6.9791 -7.0390 -20.0313 -0.3191 -0.9425 0.1818
14.9934 -4.9855 -0.0756 -0.1611 -0.4603 -0.8912
-10.9812 7.0263 16.0528 0.3276 0.9084 0.1739
-8.9794 7.0352 19.0422 0.3439 0.9552 -0.0347
-10.9852 14.9876 3.0389 -0.2259 0.7488 0.6019
-3.9779 16.0190 14.0002 -0.1944 0.9560 -0.1400
10.0120 12.0171 7.9278 -0.4919 0.3667 -0.7850
-6.9905 17.9656 -5.9891 -0.6090 0.4813 0.6562
0.0144 21.9797 -1.0332 -0.8081 0.5952 0.1093
-0.9998 15.9491 -15.0207 -0.8583 0.0294 0.5762
4.0014 16.9568 -13.0496 -0.9664 0.0112 0.2272
13.0048 12.9936 -2.0918 -0.8012 0.0339 -0.6489
11.9949 9.9680 -13.0834 -0.8972 -0.3574 -0.2635
7.9935 10.9545 -17.0633 -0.9245 -0.3632 0.0958
-3.0070 7.9468 -17.9981 -0.5882 -0.2447 0.7562
9.9819 -3.0377 -19.0537 -0.5097 -0.8628 -0.0093
11.9812 -13.0059 -10.0485 -0.0122 -0.9215 -0.4379
7.9783 -11.0277 -17.0303 -0.1369 -0.9881 0.0171
6.9788 -18.0053 -10.0133 0.2802 -0.9574 -0.1647
-6.0118 -19.9855 1.0634 0.8726 -0.4110 0.2471
-8.9954 -11.9594 15.0701 0.9419 0.2965 0.0203
-10.9807 13.0091 11.0431 0.0100 0.9300 0.3490
2.0197 9.0412 18.9783 0.0229 0.7786 -0.6679
2.9881 5.9451 -21.0287 -0.7143 -0.5181 0.4919

_exptl_absorpt_coefficient_mu    23.491
_exptl_absorpt_correction_T_min  0.007
_exptl_absorpt_correction_T_max  0.046
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.858
_oxdiff_exptl_absorpt_empirical_full_max 1.271
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            17199
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.231
_diffrn_reflns_theta_max         32.028
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0225383000
_diffrn_orient_matrix_UB_12      -0.0357817000
_diffrn_orient_matrix_UB_13      0.0206501000
_diffrn_orient_matrix_UB_21      -0.0210789000
_diffrn_orient_matrix_UB_22      0.0284882000
_diffrn_orient_matrix_UB_23      0.0296979000
_diffrn_orient_matrix_UB_31      -0.0584037000
_diffrn_orient_matrix_UB_32      0.0035711000
_diffrn_orient_matrix_UB_33      -0.0306799000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  89.00   1.00   15.00    --   22.71  77.00  60.00   50
  2  ω    -44.00 -18.00   1.00   15.00    --   22.71 -77.00 -60.00   26
  3  ω     60.00  88.00   1.00   15.00    --   22.71  57.00 -30.00   28
  4  ω    -20.00  62.00   1.00   15.00    --   22.71 -99.00 -60.00   82
  5  ω      8.00  33.00   1.00   15.00    --   22.71  57.00  30.00   25
  6  ω     49.00  75.00   1.00   15.00    --   22.71  57.00  30.00   26
  7  ω      0.00  30.00   1.00   15.00    --   22.71  77.00  60.00   30
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             7829
_reflns_number_gt                6466
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Palmer, D. C. (2014). CrystalMaker. CrystalMaker Software Ltd, Begbroke, Oxfordshire, England.'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0204P)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       0.000595(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7829
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Bi1 Bi 0.18538(2) 0.26779(2) 0.56312(2) 0.01176(6) Uani 1 1 d . . . . .
Bi2 Bi -0.17382(2) 0.42060(2) 0.40813(2) 0.01194(6) Uani 1 1 d . . . . .
I1 I 0.36416(4) 0.14783(3) 0.51225(3) 0.02365(11) Uani 1 1 d . . . . .
I2 I 0.00431(4) 0.13586(3) 0.58022(3) 0.01979(10) Uani 1 1 d . . . . .
I3 I 0.01858(4) 0.30607(3) 0.35658(3) 0.01404(9) Uani 1 1 d . . . . .
I4 I -0.00390(4) 0.41305(2) 0.61074(3) 0.01324(9) Uani 1 1 d . . . . .
I5 I 0.30864(4) 0.27058(3) 0.75241(3) 0.01843(10) Uani 1 1 d . . . . .
I6 I 0.34112(4) 0.43837(2) 0.52622(3) 0.01179(8) Uani 1 1 d . . . . .
I7 I -0.30395(4) 0.42993(3) 0.21874(3) 0.02502(11) Uani 1 1 d . . . . .
I8 I -0.33995(4) 0.29321(3) 0.45776(4) 0.02353(11) Uani 1 1 d . . . . .
C1 C 0.6133(6) 0.3632(4) 0.6989(5) 0.0232(16) Uani 1 1 d . . . . .
H1A H 0.6049 0.3760 0.6359 0.028 Uiso 1 1 calc R U . . .
H1B H 0.5666 0.3110 0.7038 0.028 Uiso 1 1 calc R U . . .
N1 N 0.5630(5) 0.4369(3) 0.7439(4) 0.0122(11) Uani 1 1 d . . . . .
H1 H 0.4719 0.4382 0.7248 0.015 Uiso 1 1 calc R U . . .
C2 C 0.7490(6) 0.3501(4) 0.7433(5) 0.0163(14) Uani 1 1 d . . . . .
H2A H 0.7964 0.3376 0.6986 0.020 Uiso 1 1 calc R U . . .
H2B H 0.7579 0.3018 0.7845 0.020 Uiso 1 1 calc R U . . .
N2 N 0.7969(5) 0.4318(3) 0.7930(4) 0.0154(12) Uani 1 1 d . . . . .
H2 H 0.8880 0.4298 0.8116 0.018 Uiso 1 1 calc R U . . .
C3 C 0.6159(6) 0.5203(4) 0.7194(4) 0.0171(14) Uani 1 1 d . . . . .
H3A H 0.5972 0.5667 0.7568 0.020 Uiso 1 1 calc R U . . .
H3B H 0.5797 0.5344 0.6574 0.020 Uiso 1 1 calc R U . . .
C4 C 0.7575(5) 0.5091(4) 0.7335(4) 0.0141(13) Uani 1 1 d . . . . .
H4A H 0.7796 0.5005 0.6764 0.017 Uiso 1 1 calc R U . . .
H4B H 0.7997 0.5606 0.7611 0.017 Uiso 1 1 calc R U . . .
C5 C 0.6003(6) 0.4264(4) 0.8432(4) 0.0173(14) Uani 1 1 d . . . . .
H5A H 0.5772 0.3693 0.8600 0.021 Uiso 1 1 calc R U . . .
H5B H 0.5577 0.4689 0.8720 0.021 Uiso 1 1 calc R U . . .
C6 C 0.7423(6) 0.4386(4) 0.8738(5) 0.0210(15) Uani 1 1 d . . . . .
H6A H 0.7609 0.4948 0.9017 0.025 Uiso 1 1 calc R U . . .
H6B H 0.7775 0.3945 0.9170 0.025 Uiso 1 1 calc R U . . .
O1 O 0.9502(4) 0.9270(3) 0.6516(4) 0.0238(12) Uani 1 1 d G . . . .
H1O1 H 0.9059 0.8906 0.6728 0.05(3) Uiso 1 1 d G . . . .
H2O1 H 0.9121 0.9756 0.6486 0.18(7) Uiso 1 1 d G . . . .


_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
Bi1 I2 2.9062(5) . ?
Bi1 I5 2.9168(5) . ?
Bi1 I1 2.9360(5) . ?
Bi1 I4 3.2580(5) . ?
Bi1 I6 3.2657(4) . ?
Bi1 I3 3.3390(5) . ?
Bi2 I8 2.9049(5) . ?
Bi2 I7 2.9404(5) . ?
Bi2 I3 3.0011(4) . ?
Bi2 I6 3.1631(4) 3_566 ?
Bi2 I4 3.2501(5) . ?
Bi2 I4 3.2854(5) 3_566 ?
I4 Bi2 3.2854(5) 3_566 ?
I6 Bi2 3.1631(4) 3_566 ?
C1 N1 1.502(8) . ?
C1 C2 1.510(8) . ?
N1 C5 1.495(8) . ?
N1 C3 1.498(7) . ?
C2 N2 1.510(8) . ?
N2 C6 1.497(9) . ?
N2 C4 1.508(7) . ?
C3 C4 1.534(8) . ?
C5 C6 1.539(9) . ?

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 Bi1 I5 95.470(14) . . ?
I2 Bi1 I1 95.409(15) . . ?
I5 Bi1 I1 94.856(15) . . ?
I2 Bi1 I4 88.747(13) . . ?
I5 Bi1 I4 86.795(13) . . ?
I1 Bi1 I4 175.354(14) . . ?
I2 Bi1 I6 168.816(14) . . ?
I5 Bi1 I6 90.915(13) . . ?
I1 Bi1 I6 93.183(13) . . ?
I4 Bi1 I6 82.438(11) . . ?
I2 Bi1 I3 88.191(13) . . ?
I5 Bi1 I3 167.408(14) . . ?
I1 Bi1 I3 96.791(14) . . ?
I4 Bi1 I3 81.233(11) . . ?
I6 Bi1 I3 83.688(12) . . ?
I8 Bi2 I7 95.564(16) . . ?
I8 Bi2 I3 101.045(14) . . ?
I7 Bi2 I3 89.102(14) . . ?
I8 Bi2 I6 86.485(13) . 3_566 ?
I7 Bi2 I6 95.268(13) . 3_566 ?
I3 Bi2 I6 170.914(13) . 3_566 ?
I8 Bi2 I4 89.174(14) . . ?
I7 Bi2 I4 174.200(15) . . ?
I3 Bi2 I4 86.702(12) . . ?
I6 Bi2 I4 88.346(12) 3_566 . ?
I8 Bi2 I4 167.806(15) . 3_566 ?
I7 Bi2 I4 92.396(14) . 3_566 ?
I3 Bi2 I4 88.278(12) . 3_566 ?
I6 Bi2 I4 83.593(11) 3_566 3_566 ?
I4 Bi2 I4 83.484(12) . 3_566 ?
Bi2 I3 Bi1 97.161(13) . . ?
Bi2 I4 Bi1 93.998(12) . . ?
Bi2 I4 Bi2 96.516(12) . 3_566 ?
Bi1 I4 Bi2 95.581(12) . 3_566 ?
Bi2 I6 Bi1 97.844(12) 3_566 . ?
N1 C1 C2 108.9(5) . . ?
C5 N1 C3 108.4(5) . . ?
C5 N1 C1 110.0(5) . . ?
C3 N1 C1 109.5(5) . . ?
C1 C2 N2 108.2(5) . . ?
C6 N2 C4 109.4(5) . . ?
C6 N2 C2 108.5(5) . . ?
C4 N2 C2 109.8(5) . . ?
N1 C3 C4 107.9(5) . . ?
N2 C4 C3 108.6(5) . . ?
N1 C5 C6 108.9(5) . . ?
N2 C6 C5 108.0(6) . . ?

_refine_diff_density_max         1.975
_refine_diff_density_min         -1.791
_refine_diff_density_rms         0.327

####################################################################### 
# 
# 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_Structure_V
_database_code_depnum_ccdc_archive 'CCDC 1580944'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT417_Structure_V         
;
PROBLEM: Short Inter D-H..H-D     H1B      ..H1O2      ..       1.68 Ang.
RESPONSE: Hydrogen positions only estimated in heavy atom containing structure therefore hydrogen-hydrogen distances are not accurate
;
_vrf_PLAT420_Structure_V         
;
PROBLEM: D-H Without Acceptor      O2       --H1O2      .     Please Check
RESPONSE: Hydrogen positions only estimated in heavy atom containing structure therefore hydrogen-hydrogen distances are not accurate
;
# Added during the CSD deposition process: Wednesday 20 December 2017 02:20 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1,4-dipiperazinium iodoantimonate tetrahydrate'
_chemical_formula_moiety         'Sb I4, 0.5(C4 N2 H12), 2(H2O)'
_chemical_formula_sum            'C2 H10 I4 N O2 Sb'
_chemical_formula_weight         709.46

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.3391(2)
_cell_length_b                   13.0022(5)
_cell_length_c                   13.8121(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.550(3)
_cell_angle_gamma                90
_cell_volume                     1313.86(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    4555
_cell_measurement_theta_min      3.8880
_cell_measurement_theta_max      31.4780
_cell_oxdiff_length_a            7.3377(4)
_cell_oxdiff_length_b            13.0043(8)
_cell_oxdiff_length_c            13.8125(6)
_cell_oxdiff_angle_alpha         89.999(4)
_cell_oxdiff_angle_beta          94.551(4)
_cell_oxdiff_angle_gamma         89.920(5)
_cell_oxdiff_volume              1313.86(12)
_cell_oxdiff_measurement_reflns_used 4555

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    3.587
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.082
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 11 -14 0.1649
-10 1 -2 0.1275
-10 -4 5 0.1287
0 -12 15 0.0399
8 -6 8 0.1816
0 -14 -13 0.0418
8 -8 -9 0.1859
-2 -14 -12 0.0447
-9 7 -2 0.1198
0 2 19 0.0475
2 2 19 0.0600
0 15 11 0.0361
-10 2 3 0.1278
-1 18 -2 0.0418
6 15 -3 0.1766
-2 13 -13 0.0497
-2 1 -19 0.0462
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.5582 11.1256 -13.5317 0.5734 -0.6719 -0.4687
-10.1983 1.0471 -1.5293 0.1240 -0.1406 0.9823
-9.8460 -4.4215 5.1843 -0.1749 0.2085 0.9622
0.2267 -11.9604 14.6704 -0.6502 0.7597 0.0087
8.3449 -6.3734 8.0154 -0.4007 0.4647 -0.7896
0.4875 -13.8644 -12.7420 0.7597 0.6502 0.0093
8.1317 -8.3038 -9.3593 0.5009 0.4316 -0.7502
-1.7179 -13.7631 -12.1635 0.7412 0.6336 0.2215
-9.3886 7.0276 -1.8713 0.0881 -0.4594 0.8838
0.1023 2.3371 19.2378 -0.9992 0.0250 -0.0314
1.6561 2.4851 18.7338 -0.9831 0.0241 -0.1816
-0.1605 15.0663 11.0827 -0.6868 -0.7255 -0.0438
-10.2584 1.5847 3.3685 -0.1294 -0.1318 0.9828
-1.1868 18.0608 -2.2838 -0.0252 -0.9982 0.0544
6.1109 14.7142 -2.6758 -0.0170 -0.7694 -0.6386
-1.6516 13.0902 -12.9805 0.5626 -0.8174 0.1238
-1.7079 1.3074 -18.8400 0.9577 -0.2294 0.1737

_exptl_absorpt_coefficient_mu    11.464
_exptl_absorpt_correction_T_min  0.043
_exptl_absorpt_correction_T_max  0.240
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.673
_oxdiff_exptl_absorpt_empirical_full_max 1.246
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            9072
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.348
_diffrn_reflns_theta_max         32.026
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4084
_reflns_number_gt                3521
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0053663000
_diffrn_orient_matrix_UB_12      -0.0081882000
_diffrn_orient_matrix_UB_13      -0.0509158000
_diffrn_orient_matrix_UB_21      0.0070941000
_diffrn_orient_matrix_UB_22      -0.0538167000
_diffrn_orient_matrix_UB_23      0.0077981000
_diffrn_orient_matrix_UB_31      -0.0965623000
_diffrn_orient_matrix_UB_32      -0.0034223000
_diffrn_orient_matrix_UB_33      -0.0007020000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  40.00   1.00   12.00    --   23.53 -57.00 -60.00   84
  2  ω    -22.00   4.00   1.00   12.00    --  -22.90 -77.00 -90.00   26
  3  ω    -89.00  -6.00   1.00   12.00    --  -22.90 -57.00-120.00   83
  4  ω      0.00  83.00   1.00   12.00    --   23.53  77.00-180.00   83
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Palmer, D. C. (2014). CrystalMaker. CrystalMaker Software Ltd, Begbroke, Oxfordshire, England.'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0083P)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       0.00083(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4084
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0470
_refine_ls_wR_factor_gt          0.0442
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
Sb1 Sb 0.76045(4) 0.97932(2) 0.09018(2) 0.01318(7) Uani 1 1 d . . . . .
I1 I 0.93834(4) 1.08050(2) 0.25744(2) 0.01986(7) Uani 1 1 d . . . . .
I2 I 0.43776(4) 1.11859(2) 0.10373(2) 0.01787(7) Uani 1 1 d . . . . .
I3 I 0.62568(4) 0.81939(2) 0.20177(2) 0.01894(7) Uani 1 1 d . . . . .
I4 I 1.09205(4) 0.84788(2) 0.06024(2) 0.01746(7) Uani 1 1 d . . . . .
N1 N 0.4721(5) 0.9169(3) 0.4321(3) 0.0290(10) Uani 1 1 d . . . . .
H1A H 0.3991 0.8794 0.3914 0.035 Uiso 1 1 calc R U . . .
H1B H 0.5850 0.8921 0.4315 0.035 Uiso 1 1 calc R U . . .
C1 C 0.5889(6) 1.0919(4) 0.4686(3) 0.0215(10) Uani 1 1 d . . . . .
H1C H 0.7150 1.0695 0.4687 0.026 Uiso 1 1 calc R U . . .
H1D H 0.5827 1.1633 0.4481 0.026 Uiso 1 1 calc R U . . .
C2 C 0.4694(6) 1.0268(4) 0.3981(3) 0.0233(10) Uani 1 1 d . . . . .
H2A H 0.3451 1.0527 0.3939 0.028 Uiso 1 1 calc R U . . .
H2B H 0.5142 1.0306 0.3340 0.028 Uiso 1 1 calc R U . . .
O1 O 0.8469(4) 1.3373(2) 0.1674(2) 0.0283(8) Uani 1 1 d G . . . .
H1O1 H 0.8473 1.2756 0.1905 0.08(2) Uiso 1 1 d G . . . .
H2O1 H 0.8650 1.3770 0.2172 0.09(3) Uiso 1 1 d G . . . .
O2 O 0.8484(5) 0.6262(2) -0.0393(3) 0.0338(9) Uani 1 1 d G . . . .
H1O2 H 0.7835 0.6719 -0.0720 0.27(7) Uiso 1 1 d G . . . .
H2O2 H 0.9465 0.6575 -0.0178 0.29(7) Uiso 1 1 d G . . . .


_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 I3 2.8143(4) . ?
Sb1 I1 2.8799(4) . ?
Sb1 I2 2.9988(4) . ?
Sb1 I4 3.0288(4) . ?
Sb1 I2 3.2081(4) 3_675 ?
I2 Sb1 3.2080(4) 3_675 ?
N1 C1 1.480(5) 3_676 ?
N1 C2 1.503(6) . ?
C1 N1 1.480(5) 3_676 ?
C1 C2 1.517(7) . ?

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
I3 Sb1 I1 93.143(12) . . ?
I3 Sb1 I2 95.646(11) . . ?
I1 Sb1 I2 89.089(11) . . ?
I3 Sb1 I4 88.793(12) . . ?
I1 Sb1 I4 92.820(11) . . ?
I2 Sb1 I4 175.068(13) . . ?
I3 Sb1 I2 90.470(11) . 3_675 ?
I1 Sb1 I2 176.090(14) . 3_675 ?
I2 Sb1 I2 89.066(10) . 3_675 ?
I4 Sb1 I2 88.749(10) . 3_675 ?
Sb1 I2 Sb1 90.934(10) . 3_675 ?
C1 N1 C2 111.5(4) 3_676 . ?
N1 C1 C2 110.5(3) 3_676 . ?
N1 C2 C1 109.7(4) . . ?

_refine_diff_density_max         1.143
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.226

####################################################################### 
# 
# 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_Structure_X
_database_code_depnum_ccdc_archive 'CCDC 1580949'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1-ethyl-2-methylbenzimidazolium iodoantimonate'
_chemical_formula_moiety         'Sb I4, (C10 N2 H13)'
_chemical_formula_sum            'C10 H13 I4 N2 Sb'
_chemical_formula_weight         790.58

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.5877(3)
_cell_length_b                   17.7055(8)
_cell_length_c                   13.2578(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.309(4)
_cell_angle_gamma                90
_cell_volume                     1776.07(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    149.95(13)
_cell_measurement_reflns_used    2417
_cell_measurement_theta_min      4.5510
_cell_measurement_theta_max      31.3940
_cell_oxdiff_length_a            7.5835(4)
_cell_oxdiff_length_b            17.7079(10)
_cell_oxdiff_length_c            13.2621(8)
_cell_oxdiff_angle_alpha         90.017(5)
_cell_oxdiff_angle_beta          94.235(5)
_cell_oxdiff_angle_gamma         90.075(5)
_cell_oxdiff_volume              1776.08(18)
_cell_oxdiff_measurement_reflns_used 2417

_exptl_crystal_description       Plate
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    2.957
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.090
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 18 0.0447
-5 22 0 0.1125
8 -15 1 0.1532
0 -25 -1 0.0611
-1 -3 -18 0.0517
1 -2 -19 0.0571
-4 21 7 0.0872
0 23 8 0.0928
-1 20 -11 0.0933
5 -5 16 0.0965
-1 8 -18 0.0597
0 0 19 0.0325
-11 1 2 0.1424
0 -16 -14 0.0466
8 -10 -10 0.1455
-1 -1 19 0.0267
1 -8 18 0.0309
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0029 5.0096 17.9679 -0.9238 -0.2821 -0.1895
-4.9975 21.9600 -0.0132 0.0584 -0.9311 0.3493
7.9949 -14.9602 1.0081 -0.0567 0.6887 -0.6720
0.0014 -24.9698 -0.9843 -0.0580 0.9904 0.1379
-1.0022 -3.0146 -17.9692 0.9249 0.1905 0.2717
0.9960 -2.0117 -18.9678 0.9974 0.1813 0.0907
-3.9970 20.9699 6.9761 -0.3061 -0.9120 0.1982
-0.0000 22.9784 7.9740 -0.3187 -0.9446 -0.1913
-1.0024 19.9629 -10.9935 0.6588 -0.7493 0.0896
4.9993 -4.9670 15.9776 -0.8241 0.1853 -0.5824
-1.0029 7.9717 -17.9754 0.9736 -0.2431 0.2151
0.0034 0.0167 18.9691 -0.9985 -0.0897 -0.1729
-10.9912 0.9726 1.9944 -0.1863 -0.1891 0.9943
-0.0015 -15.9924 -13.9682 0.6650 0.6969 0.2098
7.9926 -9.9761 -9.9768 0.5435 0.5435 -0.5976
-0.9958 -0.9846 18.9695 -1.0107 -0.0631 -0.0752
1.0029 -7.9717 17.9754 -0.9736 0.2431 -0.2151
_exptl_absorpt_coefficient_mu    8.489
_exptl_absorpt_correction_T_min  0.092
_exptl_absorpt_correction_T_max  0.427
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.688
_oxdiff_exptl_absorpt_empirical_full_max 1.399
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_diffrn_ambient_temperature      149.95(13)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            6986
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.290
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0077849000
_diffrn_orient_matrix_UB_12      0.0043997000
_diffrn_orient_matrix_UB_13      -0.0526440000
_diffrn_orient_matrix_UB_21      0.0128623000
_diffrn_orient_matrix_UB_22      -0.0394763000
_diffrn_orient_matrix_UB_23      -0.0046980000
_diffrn_orient_matrix_UB_31      -0.0925751000
_diffrn_orient_matrix_UB_32      -0.0051687000
_diffrn_orient_matrix_UB_33      -0.0090921000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00  61.00   1.00   10.03    --   23.53 -99.00 -30.00   37
  2  ω    -62.00 -36.00   1.00   10.03    --  -22.90-178.00 -60.00   26
  3  ω    -90.00   0.00   1.00   10.03    --  -22.90 -77.00-180.00   90
  4  ω    -89.00  -6.00   1.00   10.03    --  -22.90 -57.00  60.00   83
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             3104
_reflns_number_gt                1967
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Palmer, D. C. (2014). CrystalMaker. CrystalMaker Software Ltd, Begbroke, Oxfordshire, England.'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0153P)²+15.4339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3104
_refine_ls_number_parameters     266
_refine_ls_number_restraints     272
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.0927
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.145
_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
Sb1 Sb 0.74924(12) 0.07276(4) 1.50163(6) 0.02118(17) Uani 1 1 d . . . . .
I1 I 0.90922(12) 0.17927(5) 1.63978(6) 0.0389(2) Uani 1 1 d . . . . .
I2 I 1.06118(10) 0.06809(4) 1.37271(5) 0.0274(2) Uani 1 1 d . . . . .
I3 I 0.58625(11) 0.18119(5) 1.36796(6) 0.0386(2) Uani 1 1 d . . . . .
I4 I 0.43580(10) 0.06519(4) 1.63038(5) 0.0278(2) Uani 1 1 d . . . . .
C1 C 1.135(4) 0.2916(14) 1.384(2) 0.034(5) Uani 0.55 1 d D U P A 1
H1A H 1.1888 0.2541 1.4282 0.052 Uiso 0.55 1 calc R U P A 1
H1B H 1.1782 0.2864 1.3179 0.052 Uiso 0.55 1 calc R U P A 1
H1C H 1.0088 0.2847 1.3786 0.052 Uiso 0.55 1 calc R U P A 1
C2 C 1.219(3) 0.4945(15) 1.4308(19) 0.029(2) Uani 0.55 1 d D U P A 1
N3 N 1.227(3) 0.3900(11) 1.5203(13) 0.033(3) Uani 0.55 1 d D U P A 1
C4 C 1.223(3) 0.5707(13) 1.4021(17) 0.029(2) Uani 0.55 1 d D U P A 1
H4 H 1.1996 0.5881 1.3363 0.035 Uiso 0.55 1 calc R U P A 1
C5 C 1.305(4) 0.5899(13) 1.5839(19) 0.037(6) Uani 0.55 1 d D U P A 1
H5 H 1.3347 0.6238 1.6359 0.044 Uiso 0.55 1 calc R U P A 1
C7 C 1.268(3) 0.6180(14) 1.4869(16) 0.030(2) Uani 0.55 1 d D U P A 1
H7 H 1.2727 0.6700 1.4769 0.036 Uiso 0.55 1 calc R U P A 1
C8 C 1.299(4) 0.5150(14) 1.6067(17) 0.035(6) Uani 0.55 1 d D U P A 1
H8 H 1.3255 0.4975 1.6723 0.043 Uiso 0.55 1 calc R U P A 1
N9 N 1.179(2) 0.4340(9) 1.3686(13) 0.029(2) Uani 0.55 1 d D U P A 1
H9 H 1.1564 0.4356 1.3040 0.035 Uiso 0.55 1 calc R U P A 1
C10 C 1.254(3) 0.4669(12) 1.529(2) 0.029(2) Uani 0.55 1 d D U P A 1
C12 C 1.180(3) 0.3721(11) 1.4265(17) 0.035(2) Uani 0.55 1 d D U P A 1
N3A N 1.330(3) 0.4344(11) 1.6323(15) 0.037(4) Uani 0.45 1 d D U P B 2
H3A H 1.3617 0.4360 1.6960 0.044 Uiso 0.45 1 calc R U P B 2
C1A C 1.365(7) 0.2910(17) 1.614(3) 0.063(12) Uani 0.45 1 d D U P B 2
H1AA H 1.4444 0.2924 1.6737 0.094 Uiso 0.45 1 calc R U P B 2
H1AB H 1.4178 0.2630 1.5621 0.094 Uiso 0.45 1 calc R U P B 2
H1AC H 1.2565 0.2671 1.6292 0.094 Uiso 0.45 1 calc R U P B 2
C12A C 1.326(4) 0.3732(12) 1.5762(18) 0.035(5) Uani 0.45 1 d D U P B 2
N9A N 1.274(4) 0.3903(13) 1.4803(16) 0.046(4) Uani 0.45 1 d D U P B 2
C10A C 1.278(5) 0.4951(19) 1.574(2) 0.041(6) Uani 0.45 1 d D U P B 2
C2A C 1.249(4) 0.4673(14) 1.476(3) 0.034(5) Uani 0.45 1 d D U P B 2
C8A C 1.276(7) 0.5707(18) 1.595(2) 0.054(5) Uani 0.45 1 d D U P B 2
H8A H 1.3065 0.5894 1.6597 0.065 Uiso 0.45 1 calc R U P B 2
C4A C 1.202(4) 0.5130(17) 1.3925(19) 0.037(6) Uani 0.45 1 d D U P B 2
H4A H 1.1791 0.4942 1.3273 0.044 Uiso 0.45 1 calc R U P B 2
C5A C 1.228(5) 0.6168(18) 1.516(2) 0.054(5) Uani 0.45 1 d D U P B 2
H5A H 1.2161 0.6681 1.5290 0.065 Uiso 0.45 1 calc R U P B 2
C7A C 1.194(6) 0.5913(16) 1.417(2) 0.054(5) Uani 0.45 1 d D U P B 2
H7A H 1.1658 0.6261 1.3659 0.065 Uiso 0.45 1 calc R U P B 2
C50 C 1.225(3) 0.3436(13) 1.6099(17) 0.036(3) Uani 0.55 1 d . U P A 1
H50A H 1.1275 0.3081 1.6000 0.043 Uiso 0.55 1 calc R U P A 1
H50B H 1.2000 0.3759 1.6663 0.043 Uiso 0.55 1 calc R U P A 1
C50A C 1.261(4) 0.3362(19) 1.396(2) 0.047(4) Uani 0.45 1 d . U P B 2
H50C H 1.3435 0.2951 1.4108 0.057 Uiso 0.45 1 calc R U P B 2
H50D H 1.2932 0.3611 1.3350 0.057 Uiso 0.45 1 calc R U P B 2
C3 C 1.080(5) 0.305(2) 1.380(3) 0.041(7) Uani 0.45 1 d . U P B 2
H3B H 1.0821 0.2615 1.3371 0.062 Uiso 0.45 1 calc R U P B 2
H3C H 1.0042 0.3429 1.3472 0.062 Uiso 0.45 1 calc R U P B 2
H3D H 1.0375 0.2918 1.4434 0.062 Uiso 0.45 1 calc R U P B 2
C15 C 1.392(5) 0.2993(15) 1.639(2) 0.034(4) Uani 0.55 1 d . U P A 1
H15A H 1.4332 0.2755 1.5804 0.051 Uiso 0.55 1 calc R U P A 1
H15B H 1.3678 0.2614 1.6882 0.051 Uiso 0.55 1 calc R U P A 1
H15C H 1.4816 0.3330 1.6681 0.051 Uiso 0.55 1 calc R U P A 1


_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 I3 2.8330(11) . ?
Sb1 I1 2.8372(11) . ?
Sb1 I2 3.0230(12) . ?
Sb1 I4 3.0327(12) . ?
C1 C12 1.56(3) . ?
C2 N9 1.37(2) . ?
C2 C10 1.39(2) . ?
C2 C4 1.40(3) . ?
N3 C12 1.31(2) . ?
N3 C10 1.38(3) . ?
N3 C50 1.45(3) . ?
C4 C7 1.42(3) . ?
C5 C8 1.36(3) . ?
C5 C7 1.39(3) . ?
C8 C10 1.36(3) . ?
N9 C12 1.34(2) . ?
N3A C12A 1.31(2) . ?
N3A C10A 1.37(3) . ?
C1A C12A 1.56(3) . ?
C12A N9A 1.34(2) . ?
N9A C2A 1.38(3) . ?
N9A C50A 1.47(4) . ?
C10A C8A 1.37(3) . ?
C10A C2A 1.39(3) . ?
C2A C4A 1.40(3) . ?
C8A C5A 1.35(3) . ?
C4A C7A 1.43(3) . ?
C5A C7A 1.40(3) . ?
C50 C15 1.52(4) . ?
C50A C3 1.48(5) . ?

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
I3 Sb1 I1 95.68(3) . . ?
I3 Sb1 I2 89.34(3) . . ?
I1 Sb1 I2 93.90(3) . . ?
I3 Sb1 I4 93.33(3) . . ?
I1 Sb1 I4 88.95(3) . . ?
I2 Sb1 I4 175.89(3) . . ?
N9 C2 C10 108(3) . . ?
N9 C2 C4 127(2) . . ?
C10 C2 C4 126(2) . . ?
C12 N3 C10 110.1(19) . . ?
C12 N3 C50 128.8(19) . . ?
C10 N3 C50 120(2) . . ?
C2 C4 C7 111(2) . . ?
C8 C5 C7 123(3) . . ?
C5 C7 C4 123(3) . . ?
C5 C8 C10 117(2) . . ?
C12 N9 C2 107.6(18) . . ?
C8 C10 N3 135(2) . . ?
C8 C10 C2 121(2) . . ?
N3 C10 C2 105(3) . . ?
N3 C12 N9 109.8(15) . . ?
N3 C12 C1 127(2) . . ?
N9 C12 C1 123(2) . . ?
C12A N3A C10A 109(2) . . ?
N3A C12A N9A 110.2(17) . . ?
N3A C12A C1A 126(2) . . ?
N9A C12A C1A 123(2) . . ?
C12A N9A C2A 107(2) . . ?
C12A N9A C50A 125(2) . . ?
C2A N9A C50A 128(2) . . ?
C8A C10A N3A 131(3) . . ?
C8A C10A C2A 122(3) . . ?
N3A C10A C2A 106(3) . . ?
N9A C2A C10A 108(3) . . ?
N9A C2A C4A 129(3) . . ?
C10A C2A C4A 123(3) . . ?
C5A C8A C10A 116(3) . . ?
C2A C4A C7A 113(2) . . ?
C8A C5A C7A 124(3) . . ?
C5A C7A C4A 121(3) . . ?
N3 C50 C15 116(2) . . ?
N9A C50A C3 111(3) . . ?

_refine_diff_density_max         1.515
_refine_diff_density_min         -1.498
_refine_diff_density_rms         0.182


# start Validation Reply Form
_vrf_PLAT790_Structure_X         
;
PROBLEM: Centre of Gravity not Within Unit Cell: Resd.  #          1 Note  
RESPONSE: ...
;
# end Validation Reply Form

####################################################################### 
# 
# 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_Structure_VII
_database_code_depnum_ccdc_archive 'CCDC 1580946'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT201_Structure_VII       
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          4 Report
RESPONSE: Organic component of main residue modelled with a minor disorder split by PARTS instruction in close proximity
;
_vrf_PLAT420_Structure_VII       
;
PROBLEM: D-H Without Acceptor      Ow2      --Hw2B      .     Please Check
RESPONSE: Hydrogen positions only estimated in heavy atom containing structure therefore hydrogen-hydrogen distances are not accurate
;
# Added during the CSD deposition process: Wednesday 20 December 2017 04:02 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1,4-dimethyl-1,4-dipiperazinium iodoantimonate dihydrate'
_chemical_formula_iupac          '[CH3NH(CH2)4NHCH3][SbI4]2.2H2O'
_chemical_formula_moiety         'Sb2 I8, (C6 N2 H16), 2(H2O)'
_chemical_formula_sum            'C3 H10 I4 N O Sb'
_chemical_formula_weight         705.49

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.7213(2)
_cell_length_b                   12.8027(3)
_cell_length_c                   13.4527(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.377(2)
_cell_angle_gamma                90
_cell_volume                     1318.84(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    149.99(10)
_cell_measurement_reflns_used    4228
_cell_measurement_theta_min      4.1000
_cell_measurement_theta_max      31.6080
_cell_oxdiff_length_a            7.7235(4)
_cell_oxdiff_length_b            12.8012(5)
_cell_oxdiff_length_c            13.4495(5)
_cell_oxdiff_angle_alpha         89.990(3)
_cell_oxdiff_angle_beta          97.348(4)
_cell_oxdiff_angle_gamma         89.981(4)
_cell_oxdiff_volume              1318.84(10)
_cell_oxdiff_measurement_reflns_used 4228

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.179
_exptl_crystal_density_diffrn    3.553
_exptl_crystal_F_000             1224.000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -17 -7 0.0912
7 13 5 0.0942
-5 16 6 0.0879
0 17 7 0.0858
-9 2 -8 0.0833
5 6 -17 0.1112
9 -3 -13 0.1142
5 -4 -17 0.0997
-5 -4 -15 0.0802
-9 -2 -7 0.0681
-10 -5 -4 0.0697
-5 -11 -11 0.0838
8 -10 -10 0.1160
-10 -7 2 0.0783
-8 11 -3 0.1008
5 16 -5 0.1096
-2 -17 5 0.0734
4 -16 5 0.1166
8 8 -11 0.1035
-1 -11 15 0.0893
-8 -9 11 0.0982
8 2 -15 0.1012
5 3 15 0.1345
0 3 19 0.1053
-1 13 13 0.0855
-4 12 13 0.0943
7 9 -12 0.0970
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9966 -16.9919 -6.9919 -0.9980 -0.1667 -0.0217
6.9929 12.9854 4.9920 0.7390 0.1282 -0.6989
-4.9919 15.9968 5.9942 0.9312 0.1916 0.3994
0.0021 16.9908 6.9916 0.9961 0.1648 -0.0707
-8.9898 2.0085 -7.9890 -0.1028 0.4375 0.8800
4.9917 5.9909 -16.9835 -0.1811 0.9318 -0.3629
8.9867 -3.0084 -12.9884 -0.5090 0.4870 -0.7444
4.9911 -4.0036 -16.9830 -0.6564 0.6480 -0.3476
-4.9962 -3.9927 -14.9823 -0.5837 0.5770 0.5641
-8.9900 -1.9893 -6.9899 -0.2661 0.2787 0.8797
-9.9885 -4.9865 -3.9927 -0.3262 0.0594 0.9576
-4.9961 -10.9888 -10.9862 -0.8089 0.1969 0.5493
7.9880 -10.0034 -9.9910 -0.7592 0.1542 -0.6604
-9.9878 -6.9852 2.0010 -0.2600 -0.2696 0.9223
-7.9898 11.0026 -2.9951 0.4574 0.4641 0.7418
4.9941 15.9857 -4.9969 0.6167 0.6710 -0.4548
-1.9979 -16.9884 4.9961 -0.6699 -0.7053 0.1790
3.9947 -15.9954 4.9943 -0.6337 -0.6888 -0.3772
7.9890 7.9867 -10.9909 0.0695 0.7103 -0.6816
-0.9973 -10.9925 14.9848 -0.1179 -0.9908 0.0135
-7.9891 -8.9861 10.9909 -0.1170 -0.7387 0.6831
7.9880 1.9899 -14.9863 -0.3231 0.7216 -0.6468
4.9962 2.9933 14.9824 0.5362 -0.6054 -0.5625
0.0029 2.9988 18.9795 0.6531 -0.7770 -0.1259
-0.9960 12.9943 12.9857 0.9691 -0.2190 -0.0104
-3.9924 11.9981 12.9866 0.9273 -0.2415 0.2684
6.9902 8.9872 -11.9896 0.0921 0.7861 -0.5843
_exptl_absorpt_coefficient_mu    11.414
_exptl_absorpt_correction_T_min  0.057
_exptl_absorpt_correction_T_max  0.109
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.910
_oxdiff_exptl_absorpt_empirical_full_max 1.164
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      149.99(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            7222
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.444
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0018392000
_diffrn_orient_matrix_UB_12      0.0475590000
_diffrn_orient_matrix_UB_13      0.0268974000
_diffrn_orient_matrix_UB_21      -0.0019591000
_diffrn_orient_matrix_UB_22      0.0283889000
_diffrn_orient_matrix_UB_23      -0.0454249000
_diffrn_orient_matrix_UB_31      -0.0925581000
_diffrn_orient_matrix_UB_32      -0.0015263000
_diffrn_orient_matrix_UB_33      -0.0063766000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  10.00   1.00    7.50    --   22.71 -57.00  90.00   26
  2  ω     11.00  45.00   1.00    7.50    --  -22.08  77.00   0.00   34
  3  ω     -3.00  90.00   1.00    7.50    --   22.71  77.00 -90.00   93
  4  ω    -20.00  61.00   1.00    7.50    --   22.71 -99.00-180.00   81
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             3513
_reflns_number_gt                3085
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Palmer, D. C. (2014). CrystalMaker. CrystalMaker Software Ltd, Begbroke, Oxfordshire, England.'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0176P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00101(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3513
_refine_ls_number_parameters     92
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0563
_refine_ls_wR_factor_gt          0.0537
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
C2 C 1.0556(12) 0.5224(8) 1.1065(8) 0.0243(19) Uiso 0.7 1 d D . P A 1
H2A H 1.1283 0.5631 1.1565 0.029 Uiso 0.7 1 calc R U P A 1
H2B H 0.9829 0.4767 1.1411 0.029 Uiso 0.7 1 calc R U P A 1
N1 N 0.8326(8) 0.5410(4) 0.9508(4) 0.0256(13) Uiso 0.7 1 d D . P A 1
H1 H 0.7468 0.4956 0.9770 0.031 Uiso 0.7 1 calc R U P A 1
C3 C 0.9389(12) 0.5963(6) 1.0369(6) 0.0255(19) Uiso 0.7 1 d D . P A 1
H3A H 0.8603 0.6327 1.0758 0.031 Uiso 0.7 1 calc R U P A 1
H3B H 1.0120 0.6483 1.0102 0.031 Uiso 0.7 1 calc R U P A 1
C1 C 0.7365(13) 0.6222(8) 0.8796(8) 0.042(3) Uiso 0.7 1 d D . P A 1
H1A H 0.6629 0.6643 0.9158 0.063 Uiso 0.7 1 calc R U P A 1
H1B H 0.8202 0.6660 0.8528 0.063 Uiso 0.7 1 calc R U P A 1
H1C H 0.6663 0.5869 0.8257 0.063 Uiso 0.7 1 calc R U P A 1
Sb1 Sb 1.26951(4) 0.98704(2) 1.09097(2) 0.01514(8) Uani 1 1 d . . . . .
I1 I 1.43639(5) 1.10134(3) 1.25725(3) 0.03113(10) Uani 1 1 d . . . . .
I2 I 1.04955(4) 0.88469(2) 0.89382(2) 0.02101(8) Uani 1 1 d . . . . .
I3 I 1.15223(4) 0.82145(2) 1.20716(2) 0.02380(8) Uani 1 1 d . . . . .
I4 I 1.58875(4) 0.85161(2) 1.06605(2) 0.02170(8) Uani 1 1 d . . . . .
N1A N 0.928(2) 0.5800(12) 0.9316(12) 0.042(4) Uiso 0.3 1 d . . P B 2
H1AA H 1.0325 0.6227 0.9301 0.051 Uiso 0.3 1 calc R U P B 2
C2A C 1.115(3) 0.4144(16) 0.9653(18) 0.045(7) Uiso 0.3 1 d . . P B 2
H2AA H 1.1197 0.3423 0.9439 0.054 Uiso 0.3 1 calc R U P B 2
H2AB H 1.2278 0.4466 0.9610 0.054 Uiso 0.3 1 calc R U P B 2
C3A C 0.974(3) 0.4719(17) 0.9011(19) 0.0255(19) Uiso 0.3 1 d . . P B 2
H3AA H 0.8694 0.4296 0.8965 0.031 Uiso 0.3 1 calc R U P B 2
H3AB H 1.0080 0.4762 0.8342 0.031 Uiso 0.3 1 calc R U P B 2
C1A C 0.782(3) 0.634(2) 0.862(2) 0.049(7) Uiso 0.3 1 d . . P B 2
H1AB H 0.8086 0.6308 0.7942 0.074 Uiso 0.3 1 calc R U P B 2
H1AC H 0.6731 0.5992 0.8662 0.074 Uiso 0.3 1 calc R U P B 2
H1AD H 0.7734 0.7056 0.8816 0.074 Uiso 0.3 1 calc R U P B 2
OW1 O 0.710(2) 0.3518(12) 1.0390(12) 0.040(3) Uiso 0.3 1 d G . P C 2
HW1A H 0.7415 0.3071 0.9982 0.059 Uiso 0.3 1 d G U P C 2
HW1B H 0.7528 0.3294 1.0964 0.059 Uiso 0.3 1 d G U P C 2
OW2 O 0.6467(10) 0.3871(5) 1.0309(5) 0.0463(17) Uiso 0.7 1 d G . P D 1
HW2A H 0.6051 0.3304 1.0051 0.069 Uiso 0.7 1 d G U P D 1
HW2B H 0.6357 0.3818 1.0927 0.069 Uiso 0.7 1 d G U P D 1


_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
C2 N1 1.473(12) 3_767 ?
C2 C3 1.539(9) . ?
N1 C2 1.473(12) 3_767 ?
N1 C3 1.506(10) . ?
N1 C1 1.538(9) . ?
Sb1 I1 2.8399(4) . ?
Sb1 I3 2.8497(4) . ?
Sb1 I2 2.9895(4) 3_777 ?
Sb1 I4 3.0671(4) . ?
Sb1 I2 3.2371(4) . ?
I2 Sb1 2.9895(4) 3_777 ?
N1A C2A 1.47(3) 3_767 ?
N1A C3A 1.50(2) . ?
N1A C1A 1.532(15) . ?
C2A N1A 1.47(3) 3_767 ?
C2A C3A 1.492(16) . ?

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 C2 C3 110.9(8) 3_767 . ?
C2 N1 C3 111.3(7) 3_767 . ?
C2 N1 C1 108.3(7) 3_767 . ?
C3 N1 C1 109.4(6) . . ?
N1 C3 C2 113.4(7) . . ?
I1 Sb1 I3 95.469(13) . . ?
I1 Sb1 I2 87.569(12) . 3_777 ?
I3 Sb1 I2 92.777(13) . 3_777 ?
I1 Sb1 I4 95.027(13) . . ?
I3 Sb1 I4 87.469(11) . . ?
I2 Sb1 I4 177.358(13) 3_777 . ?
I1 Sb1 I2 172.379(14) . . ?
I3 Sb1 I2 88.739(11) . . ?
I2 Sb1 I2 85.880(11) 3_777 . ?
I4 Sb1 I2 91.496(11) . . ?
Sb1 I2 Sb1 94.121(11) 3_777 . ?
C2A N1A C3A 113.2(16) 3_767 . ?
C2A N1A C1A 108.7(17) 3_767 . ?
C3A N1A C1A 115.6(17) . . ?
N1A C2A C3A 106.7(19) 3_767 . ?
C2A C3A N1A 118.6(19) . . ?

_refine_diff_density_max         1.006
_refine_diff_density_min         -0.854
_refine_diff_density_rms         0.202

####################################################################### 
# 
# 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_Structure_XII
_database_code_depnum_ccdc_archive 'CCDC 1580951'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT417_Structure_XII       
;
PROBLEM: Short Inter D-H..H-D     H2O1     ..H2O1      ..       1.31 Ang.
RESPONSE: Hydrogen positions only estimated in heavy atom containing hybrid stru
;
_vrf_PLAT420_Structure_XII       
;
PROBLEM: D-H Without Acceptor      O1       --H1O1      .     Please Check
RESPONSE: Hydrogen positions only estimated in heavy atom containing structure therefore hydrogen-oxygen distances are not accurate
;
_vrf_PLAT910_Structure_XII       
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note
RESPONSE: Relatively small number of missing FCF reflections likely due to omissions from initial data reduction
;
_vrf_PLAT934_Structure_XII       
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW &gt; 10 Outliers ....          2 Check
RESPONSE: Most disagreement reflections have been checked
;
# Added during the CSD deposition process: Wednesday 20 December 2017 05:27 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1,4-diazabicyclo[2.2.2]octan-diium iodoantimonate dihydrate'
_chemical_formula_moiety         'Sb4 I16, 2(C6 N2 H14), 2(H2O)'
_chemical_formula_sum            'C12 H32 I16 N4 O2 Sb4'
_chemical_formula_weight         2781.8824

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.8634(3)
_cell_length_b                   10.8965(3)
_cell_length_c                   11.2911(3)
_cell_angle_alpha                91.999(2)
_cell_angle_beta                 109.691(2)
_cell_angle_gamma                95.086(2)
_cell_volume                     1250.46(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    150.0(2)
_cell_measurement_reflns_used    18524
_cell_measurement_theta_min      3.7490
_cell_measurement_theta_max      31.6860
_cell_oxdiff_length_a            10.8634(3)
_cell_oxdiff_length_b            10.8965(3)
_cell_oxdiff_length_c            11.2911(3)
_cell_oxdiff_angle_alpha         91.999(2)
_cell_oxdiff_angle_beta          109.691(2)
_cell_oxdiff_angle_gamma         95.086(2)
_cell_oxdiff_volume              1250.46(5)
_cell_oxdiff_measurement_reflns_used 18524

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    3.694
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.324
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -15 4 0.1736
1 -9 -12 0.2142
-2 -3 -14 0.2147
-12 9 8 0.1868
-10 -7 12 0.2505
-5 9 13 0.1864
-2 0 16 0.1605
0 -5 15 0.1878
-1 9 -12 0.2136
3 -2 -16 0.2014
-2 -13 -5 0.2030
5 -15 1 0.1919
7 5 9 0.1777
-4 15 0 0.1540
-1 15 3 0.1420
-1 -14 7 0.1947
-2 -14 -3 0.1923
8 0 10 0.1618
-11 1 -7 0.1990
-15 4 2 0.1626
-2 -15 0 0.1770
6 -14 -5 0.2113
-15 3 5 0.1818
4 14 -5 0.1323
15 3 -6 0.0875
14 -7 -4 0.1698
-3 3 -13 0.2061
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9962 -14.9915 4.0033 0.0592 -0.3737 0.9291
0.9952 -8.9966 -11.9903 0.9022 0.0923 0.4373
-2.0045 -2.9975 -13.9900 1.0253 0.0548 -0.0030
-11.9905 9.0043 7.9971 -0.2540 -0.6548 -0.6876
-9.9883 -6.9888 11.9995 -0.2830 -0.8750 0.3588
-4.9924 8.9995 12.9913 -0.8240 -0.3353 -0.5026
-1.9920 0.0020 15.9915 -0.9551 -0.3643 0.1294
0.0069 -4.9969 14.9930 -0.8688 -0.3197 0.4589
-1.0055 8.9957 -11.9957 0.6372 0.2837 -0.6882
2.9916 -2.0017 -15.9912 0.9569 0.3873 0.0104
-1.9996 -12.9921 -4.9917 0.6347 -0.2557 0.6952
4.9990 -14.9959 1.0026 0.0380 0.0142 1.0115
6.9992 4.9927 8.9902 -0.9199 0.3416 -0.0753
-3.9992 14.9952 -0.0036 -0.1378 0.0269 -0.9821
-0.9997 14.9932 2.9934 -0.4370 0.1504 -0.8939
-0.9950 -13.9919 7.0012 -0.1519 -0.4038 0.9001
-1.9987 -13.9915 -2.9925 0.5251 -0.3040 0.7766
7.9996 -0.0054 9.9909 -0.9263 0.2980 0.2562
-10.9966 1.0072 -6.9918 0.8220 -0.4985 -0.3422
-14.9908 4.0088 2.0035 0.3310 -0.8160 -0.5052
-1.9973 -14.9909 0.0061 0.3514 -0.3679 0.8684
5.9958 -13.9974 -4.9946 0.3686 0.1820 0.9073
-14.9894 3.0095 5.0021 0.1573 -0.8800 -0.4134
3.9941 13.9898 -5.0036 -0.0832 0.5429 -0.8223
14.9883 2.9874 -6.0037 -0.2052 0.9973 0.0404
13.9908 -7.0067 -4.0009 -0.1111 0.7397 0.6465
-3.0041 3.0002 -12.9922 0.8846 0.0840 -0.3741

_exptl_absorpt_coefficient_mu    12.033
_exptl_absorpt_correction_T_min  0.016
_exptl_absorpt_correction_T_max  0.072
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.716
_oxdiff_exptl_absorpt_empirical_full_max 1.313
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            29319
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.545
_diffrn_reflns_theta_max         32.057
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0356635000
_diffrn_orient_matrix_UB_12      -0.0187133000
_diffrn_orient_matrix_UB_13      -0.0641655000
_diffrn_orient_matrix_UB_21      0.0568702000
_diffrn_orient_matrix_UB_22      0.0169583000
_diffrn_orient_matrix_UB_23      -0.0157007000
_diffrn_orient_matrix_UB_31      0.0189315000
_diffrn_orient_matrix_UB_32      -0.0604440000
_diffrn_orient_matrix_UB_33      0.0104560000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  90.00   1.00   15.00    --   22.86  77.00  30.00   94
  2  ω      6.00  90.00   1.00   15.00    --   22.86  57.00 150.00   84
  3  ω    -45.00  50.00   1.00   15.00    --   22.86 -77.00 -90.00   95
  4  ω    -45.00  50.00   1.00   15.00    --   22.86 -77.00-180.00   95
  5  ω    -90.00  -6.00   1.00   15.00    --  -22.24 -57.00-180.00   84
  6  ω    -20.00  62.00   1.00   15.00    --   22.86 -99.00   0.00   82
  7  ω    -20.00  62.00   1.00   15.00    --   22.86 -99.00 120.00   82
  8  ω      6.00  90.00   1.00   15.00    --   22.86  57.00 -30.00   84
  9  ω     34.00  95.00   1.00   15.00    --   22.86-178.00 120.00   61
 10  ω      4.00  92.00   1.00   15.00    --   22.86  38.00 -60.00   88
 11  ω    -90.00 -30.00   1.00   15.00    --  -22.24 -77.00 120.00   60
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P -1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             7862
_reflns_number_gt                7196
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Palmer, D. C. (2014). CrystalMaker. CrystalMaker Software Ltd, Begbroke, Oxfordshire, England.'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0201P)²+2.1564P] 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       0.00239(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7862
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0602
_refine_ls_wR_factor_gt          0.0589
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_restrained_S_all      1.181
_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
Sb1 Sb 0.30521(2) 0.48152(2) 0.32680(2) 0.01217(6) Uani 1 1 d . . . . .
Sb2 Sb 0.65437(3) 0.81456(2) 0.37277(3) 0.01474(6) Uani 1 1 d . . . . .
I1 I 0.47231(3) 0.57194(2) 0.17709(2) 0.01589(6) Uani 1 1 d . . . . .
I2 I 0.46815(3) 0.69236(2) 0.53640(2) 0.01479(6) Uani 1 1 d . . . . .
I3 I 0.10715(3) 0.64046(3) 0.22191(3) 0.02351(7) Uani 1 1 d . . . . .
I4 I 0.19136(3) 0.27658(3) 0.14308(3) 0.02419(7) Uani 1 1 d . . . . .
I5 I 0.15836(2) 0.40125(2) 0.50239(2) 0.01544(6) Uani 1 1 d . . . . .
I6 I 0.46246(3) 0.97612(3) 0.26677(3) 0.02069(6) Uani 1 1 d . . . . .
I8 I 0.82502(3) 0.99276(3) 0.54926(3) 0.02357(7) Uani 1 1 d . . . . .
I9 I 0.77275(3) 0.83092(3) 0.18592(3) 0.02762(8) Uani 1 1 d . . . . .
N2 N 0.7129(3) 0.3443(3) 0.2464(3) 0.0141(6) Uani 1 1 d . . . . .
H2 H 0.6765 0.3966 0.2958 0.017 Uiso 1 1 calc R U . . .
N1 N 0.8066(3) 0.2111(3) 0.1210(3) 0.0186(7) Uani 1 1 d . . . . .
H1 H 0.8431 0.1589 0.0715 0.022 Uiso 1 1 calc R U . . .
C6 C 0.6021(4) 0.2718(4) 0.1430(4) 0.0170(8) Uani 1 1 d . . . . .
H6A H 0.5572 0.3261 0.0801 0.020 Uiso 1 1 calc R U . . .
H6B H 0.5392 0.2319 0.1770 0.020 Uiso 1 1 calc R U . . .
C2 C 0.7947(4) 0.2567(4) 0.3308(4) 0.0186(8) Uani 1 1 d . . . . .
H2A H 0.7387 0.1952 0.3545 0.022 Uiso 1 1 calc R U . . .
H2B H 0.8552 0.3013 0.4070 0.022 Uiso 1 1 calc R U . . .
C3 C 0.8318(4) 0.3438(4) 0.0974(4) 0.0209(9) Uani 1 1 d . . . . .
H3A H 0.7788 0.3591 0.0121 0.025 Uiso 1 1 calc R U . . .
H3B H 0.9237 0.3634 0.1070 0.025 Uiso 1 1 calc R U . . .
C5 C 0.6613(4) 0.1750(4) 0.0838(4) 0.0210(9) Uani 1 1 d . . . . .
H5A H 0.6451 0.0945 0.1130 0.025 Uiso 1 1 calc R U . . .
H5B H 0.6210 0.1705 -0.0073 0.025 Uiso 1 1 calc R U . . .
C1 C 0.8713(4) 0.1942(4) 0.2583(4) 0.0197(8) Uani 1 1 d . . . . .
H1A H 0.9619 0.2311 0.2869 0.024 Uiso 1 1 calc R U . . .
H1B H 0.8708 0.1069 0.2727 0.024 Uiso 1 1 calc R U . . .
C4 C 0.7966(4) 0.4239(4) 0.1917(4) 0.0195(8) Uani 1 1 d . . . . .
H4A H 0.8759 0.4598 0.2581 0.023 Uiso 1 1 calc R U . . .
H4B H 0.7490 0.4905 0.1500 0.023 Uiso 1 1 calc R U . . .
O1 O 0.1152(4) 0.9308(4) 0.0440(4) 0.0360(9) Uani 1 1 d G . . . .
H1O1 H 0.1566 0.9825 0.1069 0.08(3) Uiso 1 1 d G . . . .
H2O1 H 0.0391 0.9559 0.0098 0.08(3) Uiso 1 1 d G . . . .


_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 I3 2.8492(4) . ?
Sb1 I4 2.8771(4) . ?
Sb1 I1 2.9984(4) . ?
Sb1 I5 3.0407(4) . ?
Sb1 I2 3.1762(4) . ?
Sb2 I8 2.7894(4) . ?
Sb2 I9 2.8197(4) . ?
Sb2 I6 2.8274(4) . ?
N2 C4 1.495(5) . ?
N2 C2 1.501(5) . ?
N2 C6 1.502(5) . ?
N1 C1 1.497(5) . ?
N1 C3 1.498(6) . ?
N1 C5 1.502(5) . ?
C6 C5 1.527(6) . ?
C2 C1 1.531(6) . ?
C3 C4 1.521(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
I3 Sb1 I4 96.656(12) . . ?
I3 Sb1 I1 94.342(11) . . ?
I4 Sb1 I1 89.782(11) . . ?
I3 Sb1 I5 88.065(10) . . ?
I4 Sb1 I5 95.219(11) . . ?
I1 Sb1 I5 174.169(12) . . ?
I3 Sb1 I2 90.583(11) . . ?
I4 Sb1 I2 172.131(12) . . ?
I1 Sb1 I2 86.588(10) . . ?
I5 Sb1 I2 88.080(10) . . ?
I8 Sb2 I9 98.331(13) . . ?
I8 Sb2 I6 94.772(12) . . ?
I9 Sb2 I6 96.023(13) . . ?
C4 N2 C2 109.7(3) . . ?
C4 N2 C6 110.2(3) . . ?
C2 N2 C6 109.3(3) . . ?
C1 N1 C3 109.1(3) . . ?
C1 N1 C5 109.4(3) . . ?
C3 N1 C5 109.8(3) . . ?
N2 C6 C5 107.6(3) . . ?
N2 C2 C1 107.9(3) . . ?
N1 C3 C4 108.5(3) . . ?
N1 C5 C6 108.7(3) . . ?
N1 C1 C2 108.1(3) . . ?
N2 C4 C3 108.1(3) . . ?

_refine_diff_density_max         1.649
_refine_diff_density_min         -1.521
_refine_diff_density_rms         0.207

####################################################################### 
# 
# 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_Structure_VIII
_database_code_depnum_ccdc_archive 'CCDC 1580947'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1,4-dimethyl-1,4-dipiperazinium iodoantimonate trihydrate'
_chemical_formula_iupac          '[CH3NH(CH2)4NHCH3][SbI4]2.2H2O'
_chemical_formula_moiety         'Sb2 I8, (C6 N2 H16), 2(H2O)'
_chemical_formula_sum            'C6 H20 I8 N2 O2 Sb2'
_chemical_formula_weight         1410.96

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.5751(2)
_cell_length_b                   12.1020(3)
_cell_length_c                   14.5071(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.630(3)
_cell_angle_gamma                90
_cell_volume                     1328.52(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    4788
_cell_measurement_theta_min      3.6690
_cell_measurement_theta_max      31.9060
_cell_oxdiff_length_a            7.5745(3)
_cell_oxdiff_length_b            12.1071(6)
_cell_oxdiff_length_c            14.5019(8)
_cell_oxdiff_angle_alpha         89.948(4)
_cell_oxdiff_angle_beta          92.598(4)
_cell_oxdiff_angle_gamma         89.973(4)
_cell_oxdiff_volume              1328.52(12)
_cell_oxdiff_measurement_reflns_used 4788

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    3.527
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.447
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.165
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -12 -15 0.0844
-4 -9 -15 0.0999
-10 4 -3 0.2337
0 11 15 0.0760
-1 13 -13 0.0890
3 12 -13 0.1273
-10 -4 6 0.2238
8 12 0 0.1773
2 17 -2 0.1066
1 -5 -19 0.1026
-3 -3 -19 0.0861
8 0 14 0.1425
2 -6 19 0.1217
2 5 -19 0.1179
-2 6 -18 0.0859
0 -17 4 0.0922
1 17 4 0.0858
1 -17 -4 0.0883
-4 -15 -5 0.0997
-3 -16 -5 0.0893
8 6 12 0.1479
2 12 14 0.0804
-2 -10 16 0.1161
2 -10 16 0.1198
0 -15 10 0.0955
10 -4 2 0.1729
0 15 -10 0.0843
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0006 -11.9843 -14.9826 0.4722 -0.8862 0.1563
-3.9947 -8.9927 -14.9846 0.4419 -0.8187 -0.3383
-9.9904 3.9857 -3.0005 0.0378 -0.0245 -0.9818
-0.0015 10.9865 14.9829 -0.4735 0.8513 -0.0515
-1.0016 12.9810 -12.9782 0.8087 0.4508 -0.3744
2.9944 11.9858 -12.9761 0.8587 0.4718 0.0008
-9.9887 -4.0031 5.9843 -0.5154 -0.2960 -0.7996
7.9896 11.9911 0.0088 0.3581 0.7921 0.5461
1.9949 16.9791 -1.9903 0.4378 0.9132 -0.0823
0.9993 -4.9939 -18.9747 0.7816 -0.5810 0.0250
-2.9969 -3.0000 -18.9765 0.7500 -0.5485 -0.3648
7.9921 0.0080 13.9854 -0.4943 0.3937 0.8230
1.9995 -5.9889 18.9728 -0.9330 0.0476 0.4060
1.9965 4.9938 -18.9708 0.9830 -0.0266 -0.0308
-1.9995 5.9890 -17.9742 0.8879 -0.0302 -0.3987
0.0031 -16.9772 3.9887 -0.4937 -0.8409 0.2772
0.9961 16.9786 4.0008 0.1502 0.9993 -0.1289
1.0018 -16.9769 -3.9996 -0.1159 -0.9620 0.3092
-3.9934 -14.9840 -5.0005 -0.1196 -0.9655 -0.1781
-2.9942 -15.9818 -5.0002 -0.1209 -1.0005 -0.0733
7.9910 5.9999 11.9902 -0.2935 0.6802 0.7209
1.9962 11.9869 13.9858 -0.3758 0.9247 0.1069
-1.9957 -9.9874 15.9733 -0.9400 -0.2936 0.0819
2.0001 -9.9838 15.9757 -0.8715 -0.2191 0.4426
0.0029 -14.9794 9.9811 -0.7274 -0.6290 0.2916
9.9904 -3.9858 2.0019 0.0073 0.0071 0.9745
-0.0029 14.9794 -9.9811 0.7274 0.6290 -0.2916

_exptl_absorpt_coefficient_mu    11.331
_exptl_absorpt_correction_T_min  0.023
_exptl_absorpt_correction_T_max  0.112
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.779
_oxdiff_exptl_absorpt_empirical_full_max 1.305
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            8996
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.277
_diffrn_reflns_theta_max         32.015
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0171456000
_diffrn_orient_matrix_UB_12      0.0184772000
_diffrn_orient_matrix_UB_13      -0.0451508000
_diffrn_orient_matrix_UB_21      0.0186080000
_diffrn_orient_matrix_UB_22      0.0536441000
_diffrn_orient_matrix_UB_23      0.0174827000
_diffrn_orient_matrix_UB_31      0.0902602000
_diffrn_orient_matrix_UB_32      -0.0146008000
_diffrn_orient_matrix_UB_33      0.0072773000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  86.00   1.00   10.00    --   22.86  38.00   0.00   82
  2  ω      7.00  78.00   1.00   10.00    --   22.86  57.00 150.00   71
  3  ω     10.00  49.00   1.00   10.00    --   22.86 -77.00  30.00   39
  4  ω    -23.00   2.00   1.00   10.00    --   22.86 -77.00  30.00   25
  5  ω    -30.00  20.00   1.00   10.00    --  -22.08  77.00 -90.00   50
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1

_reflns_number_total             4088
_reflns_number_gt                3529
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Palmer, D. C. (2014). CrystalMaker. CrystalMaker Software Ltd, Begbroke, Oxfordshire, England.'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0126P)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       0.00140(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4088
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0522
_refine_ls_wR_factor_gt          0.0501
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_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
Sb1 Sb 0.25459(3) 0.49379(2) 0.08616(2) 0.01188(7) Uani 1 1 d . . . . .
I1 I 0.57961(4) 0.36125(2) 0.08154(2) 0.01686(7) Uani 1 1 d . . . . .
I2 I 0.41382(4) 0.64170(2) 0.22042(2) 0.01976(7) Uani 1 1 d . . . . .
I3 I -0.06736(4) 0.65572(2) 0.07126(2) 0.01922(7) Uani 1 1 d . . . . .
I4 I 0.12015(4) 0.35445(2) 0.22213(2) 0.02061(8) Uani 1 1 d . . . . .
N1 N 0.6510(4) 0.4552(3) 0.4533(3) 0.0167(8) Uani 1 1 d . . . . .
H1 H 0.7068 0.4135 0.5047 0.020 Uiso 1 1 calc R U . . .
O1 O 0.1127(4) 0.6266(3) 0.4139(3) 0.0282(8) Uani 1 1 d G . . . .
H1O1 H 0.0700 0.6884 0.4311 0.06(2) Uiso 1 1 d G . . . .
H2O1 H 0.1454 0.6369 0.3583 0.047(19) Uiso 1 1 d G . . . .
C1 C 0.6418(6) 0.5750(3) 0.4814(3) 0.0191(9) Uani 1 1 d . . . . .
H1A H 0.7603 0.6026 0.4956 0.023 Uiso 1 1 calc R U . . .
H1B H 0.5907 0.6182 0.4305 0.023 Uiso 1 1 calc R U . . .
C2 C 0.5316(5) 0.5886(3) 0.5646(3) 0.0181(9) Uani 1 1 d . . . . .
H2A H 0.5875 0.5496 0.6165 0.022 Uiso 1 1 calc R U . . .
H2B H 0.5254 0.6662 0.5806 0.022 Uiso 1 1 calc R U . . .
C3 C 0.7610(6) 0.4412(4) 0.3707(3) 0.0266(11) Uani 1 1 d . . . . .
H3A H 0.8774 0.4701 0.3843 0.040 Uiso 1 1 calc R U . . .
H3B H 0.7690 0.3642 0.3557 0.040 Uiso 1 1 calc R U . . .
H3C H 0.7072 0.4805 0.3193 0.040 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
Sb1 I4 2.8207(4) . ?
Sb1 I2 2.8700(4) . ?
Sb1 I1 2.9418(4) . ?
Sb1 I3 3.1283(4) . ?
Sb1 I3 3.1944(4) 3_565 ?
I3 Sb1 3.1943(4) 3_565 ?
N1 C2 1.492(5) 3_666 ?
N1 C3 1.501(5) . ?
N1 C1 1.509(5) . ?
C1 C2 1.508(6) . ?
C2 N1 1.492(5) 3_666 ?

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
I4 Sb1 I2 92.995(12) . . ?
I4 Sb1 I1 91.110(11) . . ?
I2 Sb1 I1 91.686(11) . . ?
I4 Sb1 I3 96.745(11) . . ?
I2 Sb1 I3 87.606(11) . . ?
I1 Sb1 I3 172.139(12) . . ?
I4 Sb1 I3 89.922(11) . 3_565 ?
I2 Sb1 I3 175.915(13) . 3_565 ?
I1 Sb1 I3 91.116(10) . 3_565 ?
I3 Sb1 I3 89.213(10) . 3_565 ?
Sb1 I3 Sb1 90.788(10) . 3_565 ?
C2 N1 C3 111.4(3) 3_666 . ?
C2 N1 C1 109.5(3) 3_666 . ?
C3 N1 C1 111.0(3) . . ?
C2 C1 N1 110.7(3) . . ?
N1 C2 C1 111.4(4) 3_666 . ?

_refine_diff_density_max         1.241
_refine_diff_density_min         -0.996
_refine_diff_density_rms         0.215

####################################################################### 
# 
# 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_Structure_XI
_database_code_depnum_ccdc_archive 'CCDC 1580950'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1-ethyl-2-methylbenzimidazolium iodoantimonate'
_chemical_formula_moiety         'Bi I4, (C10 N2 H13)'
_chemical_formula_sum            'C10 H12 Bi I4 N2'
_chemical_formula_weight         876.80

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'
Bi Bi -4.1077 10.2566 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   13.3133(4)
_cell_length_b                   17.7312(4)
_cell_length_c                   7.6344(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.450(2)
_cell_angle_gamma                90
_cell_volume                     1798.92(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    6695
_cell_measurement_theta_min      3.2020
_cell_measurement_theta_max      28.9630

_exptl_crystal_description       PrismaticNeedle
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    3.237
_exptl_crystal_F_000             1524
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.079
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-12 -4 -8 0.0440
-18 -6 -1 0.0222
18 6 -1 0.0550
-4 8 -10 0.0675
-17 11 0 0.0220
-15 7 6 0.0430
-3 25 1 0.0456
6 -15 -8 0.0681
-1 -20 6 0.0582
15 -15 -1 0.0520
-6 -22 4 0.0528
-4 -24 -3 0.0661
1 -14 -9 0.0647
12 19 1 0.0527
-2 3 11 0.0496
19 -4 -1 0.0500
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-12.0310 -3.9201 -7.9733 0.2494 -0.8078 0.5746
-18.0106 -5.9485 -0.9703 0.2926 -0.9478 -0.1232
18.0041 5.9609 -1.0278 -0.2778 0.8998 0.3023
-4.0257 8.0602 -9.9872 0.4576 -0.2557 0.8739
-16.9917 11.0212 0.0216 0.8410 -0.5340 -0.1551
-14.9756 6.9849 6.0143 0.6048 -0.3822 -0.6816
-2.9742 24.9677 0.9953 0.9319 0.3979 -0.0536
5.9608 -14.9434 -7.9964 -0.6189 -0.2292 0.7406
-0.9988 -20.0094 6.0024 -0.7032 -0.3067 -0.6032
14.9846 -15.0057 -1.0164 -0.9163 0.3397 0.2119
-6.0077 -21.9839 4.0123 -0.6206 -0.6180 -0.4841
-4.0321 -23.9420 -2.9833 -0.6918 -0.7375 0.1591
0.9580 -13.9280 -8.9883 -0.4408 -0.4556 0.7784
12.0219 18.9442 0.9750 0.3169 0.9444 0.0935
-1.9616 2.9319 10.9915 0.0759 0.2357 -0.9986
18.9950 -4.0282 -1.0260 -0.6481 0.7413 0.2857
_exptl_absorpt_coefficient_mu    16.650
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.764
_oxdiff_exptl_absorpt_empirical_full_max 1.593
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            11304
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.066
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0272147000
_diffrn_orient_matrix_UB_12      0.0343660000
_diffrn_orient_matrix_UB_13      -0.0071172000
_diffrn_orient_matrix_UB_21      0.0446260000
_diffrn_orient_matrix_UB_22      0.0202976000
_diffrn_orient_matrix_UB_23      0.0239966000
_diffrn_orient_matrix_UB_31      0.0107749000
_diffrn_orient_matrix_UB_32      0.0027122000
_diffrn_orient_matrix_UB_33      -0.0896533000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  55.00   1.00    5.00    --   16.19 -99.00  30.00   75
  2  ω     -1.00  83.00   1.00    5.00    --   16.19  57.00  90.00   84
  3  ω    -11.00  84.00   1.00    5.00    --   16.19  77.00-180.00   95
  4  ω     -1.00  83.00   1.00    5.00    --   16.19  57.00 -60.00   84
  5  ω     35.00  88.00   1.00    5.00    --   16.19 178.00 -30.00   53
  6  ω    -53.00  35.00   1.00    5.00    --   16.19 -38.00 120.00   88
  7  ω    -20.00  55.00   1.00    5.00    --   16.19 -99.00 -60.00   75
  8  ω    -82.00 -34.00   1.00    5.00    --  -17.20 145.00  56.00   48
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'C 1 2/c 1'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_theta     26.32
_reflns_odcompleteness_iscentric 1
_reflns_number_total             2049
_reflns_number_gt                1956
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0173P)²+7.1833P] 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_diff_density_max         0.773
_refine_diff_density_min         -1.166
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       0.000073(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2049
_refine_ls_number_parameters     123
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0435
_refine_ls_wR_factor_gt          0.0426
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5-C8 \\sim C8-C
 with sigma of 0.02
 N1-C \\sim N7-C5
 with sigma of 0.02
 N1-C1 \\sim N7-C0AA
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C5, N1, C8, C1AA, C1, C, C2, N7, C2AA, C4, C0AA, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: N1(0.5) C2(0.5) H2A(0.5) H2B(0.5) H2C(0.5) C5(0.5) C1(0.5) H1(0.5)
 C4(0.5) H4(0.5) C3(0.5) H3(0.5) C0AA(0.5) H0AA(0.5) C(0.5) N7(0.5) C8(0.5)
 C1AA(0.5) H1AA(0.5) H1AB(0.5) C2AA(0.5) H2AA(0.5) H2AB(0.5) H2AC(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1AA(H1AA,H1AB)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C3(H3), C0AA(H0AA)
5.c Fitted hexagon refined as free rotating group:
 C5(C1,C4,C3,C0AA,C)
5.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2AA(H2AA,H2AB,H2AC)
;

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
Bi1 Bi 1.0000 0.42603(2) 0.2500 0.02455(7) Uani 1 2 d S T P . .
I1 I 0.86907(2) 0.56625(2) 0.07071(3) 0.03027(8) Uani 1 1 d . . . . .
I2 I 0.86001(3) 0.31622(2) 0.08977(4) 0.04535(10) Uani 1 1 d . . . . .
N1 N 0.4822(7) 0.3872(4) 0.2703(17) 0.0457(19) Uani 0.5 1 d D U P A -1
C2 C 0.6328(16) 0.2931(12) 0.395(4) 0.063(5) Uani 0.5 1 d . U P A -1
H2A H 0.6124 0.2803 0.5102 0.094 Uiso 0.5 1 calc R U P A -1
H2B H 0.7042 0.3009 0.4001 0.094 Uiso 0.5 1 calc R U P A -1
H2C H 0.6153 0.2527 0.3154 0.094 Uiso 0.5 1 calc R U P A -1
C5 C 0.4756(4) 0.4634(3) 0.2468(12) 0.0390(15) Uani 0.5 1 d DG U P A -1
C1 C 0.3976(4) 0.5124(4) 0.1964(11) 0.0445(19) Uani 0.5 1 d DG U P A -1
H1 H 0.3336 0.4936 0.1674 0.053 Uiso 0.5 1 calc R U P A -1
C4 C 0.4154(6) 0.5896(3) 0.1896(17) 0.055(3) Uani 0.5 1 d G U P A -1
H4 H 0.3632 0.6224 0.1559 0.066 Uiso 0.5 1 calc R U P A -1
C3 C 0.5111(7) 0.6177(3) 0.233(2) 0.055(3) Uani 0.5 1 d G U P A -1
H3 H 0.5230 0.6693 0.2284 0.066 Uiso 0.5 1 calc R U P A -1
C0AA C 0.5891(5) 0.5687(4) 0.2833(17) 0.052(3) Uani 0.5 1 d DG U P A -1
H0AA H 0.6531 0.5875 0.3124 0.062 Uiso 0.5 1 calc R U P A -1
C C 0.5713(4) 0.4915(3) 0.2902(11) 0.045(2) Uani 0.5 1 d DG U P A -1
N7 N 0.6307(6) 0.4327(4) 0.3330(11) 0.0449(16) Uani 0.5 1 d D U P A -1
C8 C 0.5749(7) 0.3711(6) 0.3273(12) 0.0411(16) Uani 0.5 1 d D U P A -1
C1AA C 0.3947(9) 0.3382(7) 0.2642(16) 0.059(2) Uani 0.5 1 d . U P A -1
H1AA H 0.3984 0.3051 0.3655 0.071 Uiso 0.5 1 calc R U P A -1
H1AB H 0.3341 0.3684 0.2685 0.071 Uiso 0.5 1 calc R U P A -1
C2AA C 0.3899(16) 0.2962(14) 0.115(3) 0.066(5) Uani 0.5 1 d . U P A -1
H2AA H 0.3689 0.3275 0.0172 0.099 Uiso 0.5 1 calc R U P A -1
H2AB H 0.3425 0.2560 0.1260 0.099 Uiso 0.5 1 calc R U P A -1
H2AC H 0.4551 0.2755 0.0972 0.099 Uiso 0.5 1 calc R U P A -1


_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
Bi1 I2 2.9132(3) . ?
Bi1 I2 2.9132(3) 2_755 ?
Bi1 I1 3.0928(3) 6_566 ?
Bi1 I1 3.0928(3) 5_765 ?
Bi1 I1 3.2873(3) . ?
Bi1 I1 3.2873(3) 2_755 ?
I1 Bi1 3.0928(3) 5_765 ?
N1 C8 1.315(15) . ?
N1 C5 1.364(8) . ?
N1 C1AA 1.453(14) . ?
C2 C8 1.65(2) . ?
C5 C1 1.3900 . ?
C5 C 1.3900 . ?
C1 C4 1.3900 . ?
C4 C3 1.3900 . ?
C3 C0AA 1.3900 . ?
C0AA C 1.3900 . ?
C N7 1.338(9) . ?
N7 C8 1.321(12) . ?
C1AA C2AA 1.36(2) . ?
C1AA C2AA 3.05(2) 2_655 ?

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 Bi1 I2 96.111(15) . 2_755 ?
I2 Bi1 I1 89.150(9) . 6_566 ?
I2 Bi1 I1 94.239(9) 2_755 6_566 ?
I2 Bi1 I1 94.240(9) . 5_765 ?
I2 Bi1 I1 89.151(9) 2_755 5_765 ?
I1 Bi1 I1 174.932(12) 6_566 5_765 ?
I2 Bi1 I1 91.197(9) . . ?
I2 Bi1 I1 171.956(10) 2_755 . ?
I1 Bi1 I1 89.209(8) 6_566 . ?
I1 Bi1 I1 86.957(7) 5_765 . ?
I2 Bi1 I1 171.955(10) . 2_755 ?
I2 Bi1 I1 91.198(9) 2_755 2_755 ?
I1 Bi1 I1 86.957(8) 6_566 2_755 ?
I1 Bi1 I1 89.210(8) 5_765 2_755 ?
I1 Bi1 I1 81.718(11) . 2_755 ?
Bi1 I1 Bi1 93.043(7) 5_765 . ?
C8 N1 C5 108.1(7) . . ?
C8 N1 C1AA 128.0(9) . . ?
C5 N1 C1AA 122.9(9) . . ?
N1 C5 C1 134.1(5) . . ?
N1 C5 C 105.9(5) . . ?
C1 C5 C 120.0 . . ?
C5 C1 C4 120.0 . . ?
C1 C4 C3 120.0 . . ?
C0AA C3 C4 120.0 . . ?
C C0AA C3 120.0 . . ?
N7 C C0AA 132.7(5) . . ?
N7 C C5 107.3(5) . . ?
C0AA C C5 120.0 . . ?
C8 N7 C 108.3(8) . . ?
N1 C8 N7 110.3(9) . . ?
N1 C8 C2 134.2(11) . . ?
N7 C8 C2 115.5(11) . . ?
C2AA C1AA N1 110.6(13) . . ?
C2AA C1AA C2AA 96.6(14) . 2_655 ?
N1 C1AA C2AA 53.0(7) . 2_655 ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT923_Structure_XI        
;
PROBLEM: S    Values in the CIF and FCF Differ by .......      0.022 Check 
RESPONSE: Small variance in goodness of fit of data an effect of shared refinement of the structural model
;
_vrf_PLAT975_Structure_XI        
;
PROBLEM: Check Calcd Resid. Dens.  1.03A   From N7              0.55 eA-3  
RESPONSE: Residual electron density in proximity to disordered organic 1-ethyl-2-methylbenzimidazolium cation within channel of hybrid structure
;
# end Validation Reply Form

####################################################################### 
# 
# 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_Structure_II
_database_code_depnum_ccdc_archive 'CCDC 1580941'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_Structure_II        
;
PROBLEM: Check Calcd Resid. Dens.  0.73A   From Bi1             2.74 eA-3
RESPONSE: Residual electron density is in close proximity to heavy atom sublattice
;
_vrf_PLAT342_Structure_II        
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.011 Ang.
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will b
;
# Added during the CSD deposition process: Wednesday 20 December 2017 01:10 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1,3-dimethyl-2-oxo-2,3-dihydropyrimidinium iodobismuthate'
_chemical_formula_moiety         'Bi I4, (C6 H9 N2 O)'
_chemical_formula_sum            'C6 H9 Bi I4 N2 O'
_chemical_formula_weight         841.75

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'
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'
Bi Bi -4.1077 10.2566 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.6424(3)
_cell_length_b                   7.6380(2)
_cell_length_c                   20.0271(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.986(2)
_cell_angle_gamma                90
_cell_volume                     1621.78(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.2(10)
_cell_measurement_reflns_used    7829
_cell_measurement_theta_min      3.8270
_cell_measurement_theta_max      31.5940
_cell_oxdiff_length_a            10.6412(3)
_cell_oxdiff_length_b            7.6382(2)
_cell_oxdiff_length_c            20.0291(7)
_cell_oxdiff_angle_alpha         89.995(3)
_cell_oxdiff_angle_beta          94.986(3)
_cell_oxdiff_angle_gamma         90.027(2)
_cell_oxdiff_volume              1621.79(9)
_cell_oxdiff_measurement_reflns_used 7829

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    3.447
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.493
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.097
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -11 -1 0.2233
-15 0 2 0.0433
15 0 -2 0.0839
0 0 28 0.0494
0 1 -28 0.0705
2 -6 -23 0.1452
-1 11 1 0.2534
10 0 19 0.0597
3 -1 27 0.0613
-2 -1 28 0.0570
13 0 -15 0.0876
8 -9 -6 0.2067
-13 0 16 0.0600
-12 0 -15 0.0503
-10 -5 -15 0.1245
-4 0 -26 0.0399
-2 -6 -23 0.1281
2 0 -28 0.0477
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.2280 -10.7290 -0.9638 -0.1617 0.0544 0.9853
-14.9968 0.2462 2.0177 -0.9072 0.3209 -0.2719
14.9985 0.1602 -1.9876 0.9163 -0.3240 0.2353
-0.4281 0.2161 28.1839 0.3326 0.9419 -0.0475
-0.0163 1.0275 -27.9998 -0.3318 -0.9406 -0.0717
2.4681 -6.1337 -23.0600 -0.2653 -0.7472 0.6093
-1.1071 10.7370 0.8073 0.1675 -0.0618 -0.9839
9.9823 0.0064 19.3667 0.8682 0.4730 0.1502
3.1830 -0.9161 26.8655 0.5179 0.8477 0.1150
-1.6773 -0.8119 28.1482 0.2323 0.9723 0.0242
13.2185 0.0506 -15.4658 0.6330 -0.7405 0.2258
7.5309 -9.1293 -6.0820 0.2018 -0.2394 0.9497
-13.1921 -0.3451 15.5227 -0.6369 0.7449 -0.1989
-12.1191 0.0895 -14.5973 -0.9397 -0.2789 -0.1977
-10.1765 -4.7095 -14.9388 -0.9238 -0.2754 0.2660
-4.4564 0.0265 -26.1321 -0.6071 -0.7926 -0.0566
-1.6148 -5.9623 -22.9649 -0.5158 -0.6760 0.5263
2.0318 -0.1779 -28.2003 -0.2317 -0.9702 0.0707
_exptl_absorpt_coefficient_mu    18.465
_exptl_absorpt_correction_T_min  0.017
_exptl_absorpt_correction_T_max  0.133
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.732
_oxdiff_exptl_absorpt_empirical_full_max 1.412
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.2(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            17919
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.359
_diffrn_reflns_theta_max         31.865
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0625360000
_diffrn_orient_matrix_UB_12      0.0210973000
_diffrn_orient_matrix_UB_13      0.0125876000
_diffrn_orient_matrix_UB_21      -0.0170927000
_diffrn_orient_matrix_UB_22      -0.0100144000
_diffrn_orient_matrix_UB_23      0.0332364000
_diffrn_orient_matrix_UB_31      0.0165520000
_diffrn_orient_matrix_UB_32      -0.0898777000
_diffrn_orient_matrix_UB_33      -0.0007465000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00   5.00   1.00    7.50    --  -21.93 -77.00   0.00   57
  2  ω    -45.00  49.00   1.00    7.50    --   22.86 -77.00  90.00   94
  3  ω     35.00  66.00   1.00    7.50    --   22.86-178.00  90.00   31
  4  ω      8.00  46.00   1.00    7.50    --   22.86  57.00-120.00   38
  5  ω     55.00  81.00   1.00    7.50    --   22.86  57.00-120.00   26
  6  ω     61.00  89.00   1.00    7.50    --   22.86  57.00-150.00   28
  7  ω      9.00  89.00   1.00    7.50    --   22.86  57.00-180.00   80
  8  ω     -3.00  90.00   1.00    7.50    --   22.86  77.00 -60.00   93
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_theta     28.22
_reflns_odcompleteness_iscentric 1
_reflns_number_total             5140
_reflns_number_gt                4534
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Palmer, D. C. (2014). CrystalMaker. CrystalMaker Software Ltd, Begbroke, Oxfordshire, England.'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0234P)²+3.8399P] 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       0.00063(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5140
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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
Bi1 Bi 0.58576(2) 0.74471(3) 0.45635(2) 0.01556(7) Uani 1 1 d . . . . .
I1 I 0.46056(4) 0.41541(5) 0.39539(2) 0.01984(9) Uani 1 1 d . . . . .
I2 I 0.60312(4) 0.86845(6) 0.31964(2) 0.03089(11) Uani 1 1 d . . . . .
I3 I 0.69229(3) 1.08197(5) 0.52894(2) 0.02194(10) Uani 1 1 d . . . . .
I4 I 0.84297(3) 0.60491(5) 0.47204(2) 0.02114(10) Uani 1 1 d . . . . .
N1 N 0.8496(4) 0.1356(7) 0.2177(3) 0.0200(10) Uani 1 1 d . . . . .
C1 C 0.8850(7) 0.0658(11) 0.1538(4) 0.0357(17) Uani 1 1 d . . . . .
H1A H 0.9503 -0.0203 0.1622 0.054 Uiso 1 1 calc R U . . .
H1B H 0.8128 0.0126 0.1299 0.054 Uiso 1 1 calc R U . . .
H1C H 0.9153 0.1593 0.1275 0.054 Uiso 1 1 calc R U . . .
C2 C 0.9163(6) 0.0706(9) 0.2747(3) 0.0233(13) Uani 1 1 d . . . . .
O1 O 0.9958(5) -0.0408(7) 0.2738(3) 0.0376(13) Uani 1 1 d . . . . .
N3 N 0.8845(4) 0.1486(7) 0.3346(3) 0.0219(11) Uani 1 1 d . . . . .
C3 C 0.9536(7) 0.0823(11) 0.3962(4) 0.0375(18) Uani 1 1 d . . . . .
H3A H 1.0152 -0.0018 0.3847 0.056 Uiso 1 1 calc R U . . .
H3B H 0.9951 0.1777 0.4202 0.056 Uiso 1 1 calc R U . . .
H3C H 0.8955 0.0275 0.4238 0.056 Uiso 1 1 calc R U . . .
C4 C 0.7605(6) 0.2571(8) 0.2183(4) 0.0247(14) Uani 1 1 d . . . . .
H4 H 0.7190 0.2959 0.1782 0.030 Uiso 1 1 calc R U . . .
C5 C 0.7298(6) 0.3259(9) 0.2784(4) 0.0266(14) Uani 1 1 d . . . . .
H5 H 0.6670 0.4104 0.2796 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7933(6) 0.2673(8) 0.3359(4) 0.0258(14) Uani 1 1 d . . . . .
H6 H 0.7725 0.3109 0.3769 0.031 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
Bi1 I2 2.9175(5) . ?
Bi1 I4 2.9295(4) . ?
Bi1 I1 3.0511(4) . ?
Bi1 I3 3.1222(4) . ?
Bi1 I3 3.2783(4) 3_676 ?
Bi1 I1 3.2878(5) 3_666 ?
I1 Bi1 3.2878(5) 3_666 ?
I3 Bi1 3.2784(4) 3_676 ?
N1 C4 1.327(8) . ?
N1 C2 1.383(8) . ?
N1 C1 1.465(8) . ?
C2 O1 1.201(7) . ?
C2 N3 1.407(8) . ?
N3 C6 1.330(8) . ?
N3 C3 1.469(8) . ?
C4 C5 1.380(10) . ?
C5 C6 1.359(10) . ?

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 Bi1 I4 94.818(14) . . ?
I2 Bi1 I1 87.282(13) . . ?
I4 Bi1 I1 96.544(12) . . ?
I2 Bi1 I3 96.869(14) . . ?
I4 Bi1 I3 87.286(12) . . ?
I1 Bi1 I3 174.118(13) . . ?
I2 Bi1 I3 94.863(14) . 3_676 ?
I4 Bi1 I3 168.474(14) . 3_676 ?
I1 Bi1 I3 90.151(11) . 3_676 ?
I3 Bi1 I3 85.358(11) . 3_676 ?
I2 Bi1 I1 174.118(13) . 3_666 ?
I4 Bi1 I1 88.830(12) . 3_666 ?
I1 Bi1 I1 87.720(12) . 3_666 ?
I3 Bi1 I1 87.897(12) . 3_666 ?
I3 Bi1 I1 82.050(12) 3_676 3_666 ?
Bi1 I1 Bi1 92.279(12) . 3_666 ?
Bi1 I3 Bi1 94.642(11) . 3_676 ?
C4 N1 C2 124.0(6) . . ?
C4 N1 C1 120.0(6) . . ?
C2 N1 C1 115.9(5) . . ?
O1 C2 N1 123.6(6) . . ?
O1 C2 N3 122.3(6) . . ?
N1 C2 N3 114.1(5) . . ?
C6 N3 C2 122.3(6) . . ?
C6 N3 C3 122.1(6) . . ?
C2 N3 C3 115.4(6) . . ?
N1 C4 C5 119.9(6) . . ?
C6 C5 C4 118.4(6) . . ?
N3 C6 C5 121.2(6) . . ?

_refine_diff_density_max         2.761
_refine_diff_density_min         -1.866
_refine_diff_density_rms         0.278

####################################################################### 
# 
# 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_Structure_IV
_database_code_depnum_ccdc_archive 'CCDC 1580943'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-methylmorpolinium iodobismuthate'
_chemical_formula_moiety         'Bi4 I16, 4(C5 H12 N O)'
_chemical_formula_sum            'C20 H48 Bi4 I16 N4 O4'
_chemical_formula_weight         3274.94

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 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_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.7627(3)
_cell_length_b                   20.7207(6)
_cell_length_c                   22.7427(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6014.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    18920
_cell_measurement_theta_min      3.4750
_cell_measurement_theta_max      31.4880
_cell_oxdiff_length_a            12.7494(4)
_cell_oxdiff_length_b            20.7355(7)
_cell_oxdiff_length_c            22.7503(8)
_cell_oxdiff_angle_alpha         89.956(3)
_cell_oxdiff_angle_beta          90.074(3)
_cell_oxdiff_angle_gamma         90.008(3)
_cell_oxdiff_volume              6014.4(4)
_cell_oxdiff_measurement_reflns_used 18920

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.144
_exptl_crystal_density_diffrn    3.617
_exptl_crystal_F_000             5632.000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 -8 28 0.1009
-2 -25 16 0.1076
-9 -26 1 0.1244
-12 -14 -19 0.1262
-8 8 -28 0.1201
7 26 -5 0.1221
12 10 22 0.0995
11 20 12 0.1094
-15 -16 5 0.1028
-16 -2 13 0.0971
-13 13 16 0.0988
-10 19 16 0.1083
16 13 -8 0.0749
13 -13 -16 0.0456
5 -4 -31 0.0894
8 6 -28 0.0865
-5 3 31 0.0931
-10 -16 20 0.0940
-3 8 30 0.1010
-14 -16 10 0.0949
-12 10 22 0.0874
-15 -9 14 0.0942
-15 15 -3 0.1064
-3 29 0 0.1309
-18 -1 -4 0.1180
-15 -16 -3 0.1113
-14 -15 -11 0.1157
-13 11 -19 0.1127
-7 23 -16 0.1292
16 -11 -3 0.0634
12 -21 -4 0.0723
-1 -2 -32 0.0981
6 17 -24 0.1098
-3 -9 30 0.1005
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.5521 -8.2458 27.6404 -0.9574 -0.2849 -0.0479
-2.2950 -24.8213 16.4258 -0.6376 -0.1871 0.7473
-8.5251 -25.7283 0.6276 -0.1098 -0.0293 0.9935
-11.7809 -13.9235 -18.7831 0.5832 0.1762 0.7930
-7.7550 7.6719 -27.6604 0.9561 0.2846 0.0705
7.2593 26.4074 -4.6218 0.2464 0.0700 -0.9666
11.6051 9.9984 21.8798 -0.7009 -0.2107 -0.6815
11.3073 19.8392 12.1454 -0.3398 -0.1042 -0.9347
-14.7119 -16.0652 5.3842 0.1362 -0.4496 0.8828
-16.4605 -1.7476 12.7773 0.2480 -0.8291 0.5011
-13.2736 13.0013 16.3007 0.2849 -0.9582 -0.0281
-10.4660 18.5715 16.3155 0.2736 -0.9227 -0.2717
15.6327 12.6949 -7.5423 -0.1705 0.5657 -0.8068
13.4602 -12.5299 -16.2577 -0.2850 0.9585 0.0089
5.0348 -4.0436 -30.9449 0.4301 0.9168 0.0443
8.0236 5.9631 -27.9480 0.4149 0.8435 -0.3403
-5.0343 3.0442 30.9465 -0.4449 -0.9062 -0.0153
-10.0074 -15.9769 19.9599 -0.3272 -0.6226 0.7078
-3.0373 8.0441 29.9494 -0.4162 -0.8691 -0.2163
-13.9921 -16.0044 9.9467 0.0166 -0.5296 0.8490
-12.0212 10.0079 21.9057 0.0805 -1.0113 0.0086
-14.9995 -9.0031 13.9272 0.0685 -0.7286 0.6660
-14.9913 14.9523 -3.0995 0.7818 -0.5961 0.0120
-3.0121 28.9772 -0.0628 0.5274 -0.4087 -0.7519
-17.9796 -1.0475 -4.0881 0.6662 -0.5046 0.5656
-14.9758 -16.0306 -3.0489 0.3243 -0.2672 0.9097
-13.9676 -15.0436 -11.0395 0.4749 -0.0620 0.8708
-12.9719 10.9295 -19.0709 0.9945 -0.1219 0.1079
-6.9866 22.9419 -16.0618 0.9094 -0.1154 -0.4224
15.9956 -10.9633 -2.8975 -0.6292 0.7240 -0.1427
12.0052 -20.9686 -3.9010 -0.6231 0.7181 0.2664
-0.9600 -2.0601 -31.9783 0.6796 0.7163 0.1645
6.0150 16.9599 -23.9792 0.5590 0.5683 -0.6100
-3.0287 -8.9465 29.9772 -0.6671 -0.6888 0.2760

_exptl_absorpt_coefficient_mu    19.909
_exptl_absorpt_correction_T_min  0.011
_exptl_absorpt_correction_T_max  0.060
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.756
_oxdiff_exptl_absorpt_empirical_full_max 1.364
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.01(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            67953
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.277
_diffrn_reflns_theta_max         32.127
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0330901000
_diffrn_orient_matrix_UB_12      0.0147153000
_diffrn_orient_matrix_UB_13      -0.0212053000
_diffrn_orient_matrix_UB_21      0.0338555000
_diffrn_orient_matrix_UB_22      -0.0106342000
_diffrn_orient_matrix_UB_23      -0.0227296000
_diffrn_orient_matrix_UB_31      -0.0292231000
_diffrn_orient_matrix_UB_32      -0.0289912000
_diffrn_orient_matrix_UB_33      -0.0023977000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -93.00   6.00   1.00   27.23    --  -22.90 -19.00  60.00   99
  2  ω    -53.00  -5.00   1.00   27.23    --  -22.90 -77.00 -90.00   48
  3  ω    -77.00   2.00   1.00   27.23    --  -22.90 -77.00   0.00   79
  4  ω    -37.00  23.00   1.00   27.23    --  -22.90  38.00-120.00   60
  5  ω     35.00  89.00   1.00   27.23    --   23.53 178.00 150.00   54
  6  ω      8.00  90.00   1.00   27.23    --   23.53  77.00-120.00   82
  7  ω     38.00  75.00   1.00   27.23    --   23.53-125.00-171.00   37
;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P b c a'
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_cell_setting           orthorhombic
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             9856
_reflns_number_gt                8469
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Palmer, D. C. (2014). CrystalMaker. CrystalMaker Software Ltd, Begbroke, Oxfordshire, England.'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0102P)²+14.1908P] 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       0.000098(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9856
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0483
_refine_ls_wR_factor_gt          0.0462
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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
Bi2 Bi 0.04508(2) 0.07882(2) 0.06760(2) 0.01291(4) Uani 1 1 d . . . . .
Bi1 Bi 0.03139(2) 0.14429(2) -0.12929(2) 0.01383(4) Uani 1 1 d . . . . .
I1 I -0.11086(3) 0.22496(2) -0.19520(2) 0.02213(7) Uani 1 1 d . . . . .
I2 I 0.14892(3) 0.10692(2) -0.23488(2) 0.02295(7) Uani 1 1 d . . . . .
I3 I 0.15442(2) 0.02805(2) -0.05110(2) 0.01481(6) Uani 1 1 d . . . . .
I4 I -0.08695(2) 0.17526(2) -0.00559(2) 0.01686(6) Uani 1 1 d . . . . .
I5 I 0.18317(3) 0.24004(2) -0.09374(2) 0.02336(8) Uani 1 1 d . . . . .
I7 I 0.21758(2) 0.16532(2) 0.08940(2) 0.02014(7) Uani 1 1 d . . . . .
I6 I 0.15433(2) -0.02619(2) 0.14047(2) 0.01886(7) Uani 1 1 d . . . . .
I8 I -0.07607(2) 0.12506(2) 0.17014(2) 0.01800(7) Uani 1 1 d . . . . .
O1 O 0.9813(3) 0.01727(17) 0.64403(15) 0.0224(8) Uani 1 1 d . . . . .
O2 O 0.0419(3) 0.41042(18) 0.97678(16) 0.0269(8) Uani 1 1 d . . . . .
N1 N 0.9080(3) -0.08749(19) 0.71448(17) 0.0164(8) Uani 1 1 d . . . . .
H1 H 0.9442 -0.0744 0.7506 0.020 Uiso 1 1 calc R U . . .
N2 N 0.0177(3) 0.3579(2) 1.09212(18) 0.0190(9) Uani 1 1 d . . . . .
H2 H 0.0226 0.3979 1.1150 0.023 Uiso 1 1 calc R U . . .
C1 C 0.8376(4) -0.0329(2) 0.6970(2) 0.0203(10) Uani 1 1 d . . . . .
H1A H 0.7860 -0.0253 0.7275 0.024 Uiso 1 1 calc R U . . .
H1B H 0.8009 -0.0437 0.6610 0.024 Uiso 1 1 calc R U . . .
C3 C 0.9896(4) -0.0968(3) 0.6681(2) 0.0229(11) Uani 1 1 d . . . . .
H3A H 0.9567 -0.1091 0.6313 0.027 Uiso 1 1 calc R U . . .
H3B H 1.0373 -0.1310 0.6796 0.027 Uiso 1 1 calc R U . . .
C6 C -0.0517(4) 0.4196(3) 1.0084(2) 0.0218(11) Uani 1 1 d . . . . .
H6A H -0.1097 0.4231 0.9811 0.026 Uiso 1 1 calc R U . . .
H6B H -0.0475 0.4596 1.0304 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8484(4) -0.1477(3) 0.7281(2) 0.0263(12) Uani 1 1 d . . . . .
H9A H 0.7973 -0.1389 0.7580 0.039 Uiso 1 1 calc R U . . .
H9B H 0.8136 -0.1626 0.6932 0.039 Uiso 1 1 calc R U . . .
H9C H 0.8959 -0.1803 0.7417 0.039 Uiso 1 1 calc R U . . .
C2 C 0.9025(4) 0.0265(3) 0.6879(2) 0.0241(11) Uani 1 1 d . . . . .
H2A H 0.8573 0.0619 0.6762 0.029 Uiso 1 1 calc R U . . .
H2B H 0.9358 0.0383 0.7248 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1175(4) 0.3506(3) 1.0577(2) 0.0238(11) Uani 1 1 d . . . . .
H8A H 0.1164 0.3103 1.0360 0.029 Uiso 1 1 calc R U . . .
H8B H 0.1769 0.3497 1.0843 0.029 Uiso 1 1 calc R U . . .
C4 C 1.0491(4) -0.0344(3) 0.6603(2) 0.0250(12) Uani 1 1 d . . . . .
H4A H 1.0843 -0.0237 0.6968 0.030 Uiso 1 1 calc R U . . .
H4B H 1.1021 -0.0401 0.6302 0.030 Uiso 1 1 calc R U . . .
C5 C -0.0718(4) 0.3647(2) 1.0502(2) 0.0227(11) Uani 1 1 d . . . . .
H5A H -0.1359 0.3728 1.0718 0.027 Uiso 1 1 calc R U . . .
H5B H -0.0805 0.3250 1.0282 0.027 Uiso 1 1 calc R U . . .
C10 C 0.0011(5) 0.3037(3) 1.1339(2) 0.0278(12) Uani 1 1 d . . . . .
H10A H 0.0598 0.3008 1.1601 0.042 Uiso 1 1 calc R U . . .
H10B H -0.0616 0.3112 1.1562 0.042 Uiso 1 1 calc R U . . .
H10C H -0.0057 0.2641 1.1123 0.042 Uiso 1 1 calc R U . . .
C7 C 0.1283(4) 0.4063(3) 1.0157(3) 0.0290(13) Uani 1 1 d . . . . .
H7A H 0.1338 0.4461 1.0379 0.035 Uiso 1 1 calc R U . . .
H7B H 0.1922 0.4011 0.9931 0.035 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
Bi2 I7 2.8819(4) . ?
Bi2 I8 2.9577(3) . ?
Bi2 I6 3.0701(4) . ?
Bi2 I4 3.0989(4) . ?
Bi2 I3 3.2157(3) . ?
Bi2 I3 3.3952(3) 5 ?
Bi1 I1 2.8873(4) . ?
Bi1 I5 2.8883(4) . ?
Bi1 I2 2.9353(4) . ?
Bi1 I4 3.2569(3) . ?
Bi1 I3 3.3807(3) . ?
Bi1 I6 3.4163(4) 5 ?
I3 Bi2 3.3951(3) 5 ?
I6 Bi1 3.4162(4) 5 ?
O1 C4 1.426(6) . ?
O1 C2 1.430(6) . ?
O2 C6 1.407(6) . ?
O2 C7 1.417(6) . ?
N1 C9 1.494(6) . ?
N1 C3 1.495(6) . ?
N1 C1 1.498(6) . ?
N2 C10 1.486(6) . ?
N2 C5 1.495(6) . ?
N2 C8 1.503(6) . ?
C1 C2 1.499(7) . ?
C3 C4 1.509(7) . ?
C6 C5 1.503(7) . ?
C8 C7 1.503(7) . ?

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
I7 Bi2 I8 93.567(10) . . ?
I7 Bi2 I6 90.053(10) . . ?
I8 Bi2 I6 92.368(10) . . ?
I7 Bi2 I4 96.127(10) . . ?
I8 Bi2 I4 86.007(10) . . ?
I6 Bi2 I4 173.693(10) . . ?
I7 Bi2 I3 90.936(10) . . ?
I8 Bi2 I3 174.129(10) . . ?
I6 Bi2 I3 91.390(9) . . ?
I4 Bi2 I3 89.772(9) . . ?
I7 Bi2 I3 175.987(11) . 5 ?
I8 Bi2 I3 84.629(9) . 5 ?
I6 Bi2 I3 86.445(9) . 5 ?
I4 Bi2 I3 87.335(9) . 5 ?
I3 Bi2 I3 91.108(8) . 5 ?
I1 Bi1 I5 99.751(11) . . ?
I1 Bi1 I2 92.829(11) . . ?
I5 Bi1 I2 93.870(11) . . ?
I1 Bi1 I4 92.451(10) . . ?
I5 Bi1 I4 86.207(10) . . ?
I2 Bi1 I4 174.628(11) . . ?
I1 Bi1 I3 167.838(10) . . ?
I5 Bi1 I3 91.756(10) . . ?
I2 Bi1 I3 90.289(10) . . ?
I4 Bi1 I3 84.340(8) . . ?
I1 Bi1 I6 86.548(10) . 5 ?
I5 Bi1 I6 168.010(11) . 5 ?
I2 Bi1 I6 96.010(10) . 5 ?
I4 Bi1 I6 83.321(9) . 5 ?
I3 Bi1 I6 81.435(8) . 5 ?
Bi2 I3 Bi1 90.399(9) . . ?
Bi2 I3 Bi2 88.894(8) . 5 ?
Bi1 I3 Bi2 93.340(8) . 5 ?
Bi2 I4 Bi1 94.862(9) . . ?
Bi2 I6 Bi1 98.764(9) . 5 ?
C4 O1 C2 110.2(4) . . ?
C6 O2 C7 110.4(4) . . ?
C9 N1 C3 113.1(4) . . ?
C9 N1 C1 112.3(4) . . ?
C3 N1 C1 109.2(4) . . ?
C10 N2 C5 111.7(4) . . ?
C10 N2 C8 112.1(4) . . ?
C5 N2 C8 108.9(4) . . ?
N1 C1 C2 109.0(4) . . ?
N1 C3 C4 108.8(4) . . ?
O2 C6 C5 111.5(4) . . ?
O1 C2 C1 112.0(4) . . ?
N2 C8 C7 109.3(4) . . ?
O1 C4 C3 111.7(4) . . ?
N2 C5 C6 110.1(4) . . ?
O2 C7 C8 111.9(4) . . ?

_refine_diff_density_max         1.492
_refine_diff_density_min         -1.247
_refine_diff_density_rms         0.244

####################################################################### 
# 
# 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_structure_xiii
_database_code_depnum_ccdc_archive 'CCDC 1580952'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT306_structure_xiii      
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......         O1 Check
RESPONSE: Water oxygen hydrogen atom positions omitted from structural model due to inaccuracies determining exact positions in heavy atoms structure
;
_vrf_PLAT306_structure_xiii_2    
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......         O3 Check
RESPONSE: Water oxygen hydrogen atom positions omitted from structural model due to inaccuracies determining exact positions in heavy atoms structure
;
# Added during the CSD deposition process: Wednesday 20 December 2017 05:33 PM
# end Validation Reply Form

_audit_creation_date             2017-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_systematic        
'1,4-diazabicyclo[2.2.2]octan-diium iodobismuthate octahydrate'
_chemical_formula_moiety         'Bi0.5 I3, Bi0.5 I2.5, O, 2(C3 H7 N)'
_chemical_formula_sum            'C7.50 H19.50 Bi I5.50 N2.50 O'
_chemical_formula_weight         1067.68
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'
Bi Bi -4.1077 10.2566 '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'
O O 0.0106 0.0060 '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           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'-x-1/2, y-1/2, z'
'x-1/2, -y-1/2, z'

_cell_length_a                   31.9562(6)
_cell_length_b                   15.8622(4)
_cell_length_c                   8.6164(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4367.62(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    23423
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      31.6690
_cell_measurement_theta_min      3.5310
_exptl_absorpt_coefficient_mu    15.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    3.247
_exptl_crystal_description       needle
_exptl_crystal_F_000             3716
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            88944
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         3.437
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1468
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6229
_reflns_number_total             7058
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'SHELXS (Sheldrick, 2008)'
_refine_diff_density_max         2.269
_refine_diff_density_min         -1.780
_refine_diff_density_rms         0.273
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         7058
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+86.6593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0723
_refine_special_details          
;
The asymmetric unit in this structure comprises half of a [BiI6]3- 
ion, one quarter of a [Bi2I10]24- ion, two crystallographically 
independent [DABCOH2]2+ halves, two half-occupancy waters, and 
some disordered electron density.
Atom I4 in the moiety based on Bi1 was modelled to take account of 
70:30 disorder, while I6 (in the dimer based on Bi2) was modelled for 
65:35 disorder.
Both bismuth centres are coincident with a crystallographic mirror plane, 
on which atoms I1, I2, I5, I6/6A, N1, N2, N3, N4, H1, H2, H3A, H4A, C3, 
C4, C7 and C8, also reside. The hydrogens attached the latter ([DABCOH2]2+) 
carbons were located, and each refined at a distance of 0.97 Å from the 
relevant parent. The nitrogen-bound hydrogens in the protonated DABCO moieties 
were included using a riding model based on evidence in the difference Fourier 
electron density map prior to their incorporation. It was impossible to locate 
the water hydrogens with any credibility and, hence, these were omitted from 
the refinement. 
Electron density in the disordered regions of the unit cell was treated using 
the solvent mask algorithm in Olex2. The output from this algorithm suggested 
that the two solvent accessible voids in the unit cell could house two additional 
[DABCOH2]2+ units and an allowance for these has been made in the motif formula 
as presented. 

Overall, the formulation for the unit cell contents is 
[Bi2I10]2[BiI6]4[C6N2H14]10.(H2O)8    

;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C7-H7 = C8-H8 = C4-H4 = C3-H3
 0.97 with sigma of 0.005
3. Others
 Fixed Sof: I4(0.7) I4A(0.3) I6(0.325) I6A(0.175)
4.a Ternary CH refined with riding coordinates:
 N1(H1), N2(H2), N3(H3A), N4(H4A)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B)
;
_atom_sites_solution_hydrogens   mixed
_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
Bi1 Bi 0.68890(2) 0.07065(2) 0.0000 0.01568(7) Uani 1 2 d S T P . .
I1 I 0.74009(2) 0.24025(4) 0.0000 0.01792(12) Uani 1 2 d S T P A .
I2 I 0.64271(3) -0.09359(5) 0.0000 0.03074(17) Uani 1 2 d S T P A .
I3 I 0.75219(2) -0.00161(3) 0.25114(5) 0.01634(8) Uani 1 1 d . . . . .
I4 I 0.6354(2) 0.1421(5) 0.2551(9) 0.0231(4) Uani 0.7 1 d . . . A 1
I4A I 0.6293(5) 0.1374(13) 0.238(2) 0.032(2) Uani 0.3 1 d . . . A 2
Bi2 Bi 0.96071(2) 0.12790(2) 0.5000 0.01970(8) Uani 1 2 d S T P . .
I5 I 0.87766(2) 0.01840(4) 0.5000 0.02052(13) Uani 1 2 d S T P B .
I7 I 1.0000 0.0000 0.24586(7) 0.01832(12) Uani 1 2 d S T P B .
I8 I 0.92539(2) 0.23107(3) 0.75409(7) 0.03059(12) Uani 1 1 d . . . . .
I6 I 1.04221(14) 0.21795(19) 0.5000 0.0381(6) Uani 0.65 2 d S T P B 1
I6A I 1.0361(3) 0.2417(3) 0.5000 0.0352(11) Uani 0.35 2 d S T P B 2
O3 O 1.0182(2) 0.1995(6) 0.0000 0.0330(19) Uani 1 2 d S T P . .
O1 O 0.8485(4) 0.4615(6) 0.5000 0.048(3) Uani 1 2 d S T P . .
N1 N 0.7861(3) 0.3259(5) 0.5000 0.0200(17) Uani 1 2 d S T P . .
H1 H 0.7861 0.3876 0.5000 0.024 Uiso 1 2 calc RS T P . .
N2 N 0.7863(2) 0.1704(5) 0.5000 0.0147(15) Uani 1 2 d S T P . .
H2 H 0.7862 0.1086 0.5000 0.018 Uiso 1 2 calc RS T P . .
C1 C 0.8084(2) 0.2010(4) 0.3582(9) 0.0224(14) Uani 1 1 d . . . . .
H1A H 0.7944 0.1803 0.2660 0.027 Uiso 1 1 calc R . . . .
H1B H 0.8370 0.1800 0.3574 0.027 Uiso 1 1 calc R . . . .
C2 C 0.8086(3) 0.2962(4) 0.3586(9) 0.0246(15) Uani 1 1 d . . . . .
H2A H 0.8371 0.3170 0.3592 0.029 Uiso 1 1 calc R . . . .
H2B H 0.7948 0.3173 0.2662 0.029 Uiso 1 1 calc R . . . .
C3 C 0.7429(3) 0.2007(7) 0.5000 0.025(2) Uani 1 2 d DS T P . .
H3 H 0.732(2) 0.182(5) 0.400(5) 0.030 Uiso 1 1 d DR . . . .
C4 C 0.7423(4) 0.2967(7) 0.5000 0.034(3) Uani 1 2 d DS T P . .
H4 H 0.728(2) 0.320(5) 0.411(6) 0.040 Uiso 1 1 d DR . . . .
N3 N 0.6634(3) 0.4239(5) 0.0000 0.0210(17) Uani 1 2 d S T P . .
H3A H 0.6940 0.4274 0.0000 0.025 Uiso 1 2 calc RS T P . .
N4 N 0.5859(2) 0.4160(5) 0.0000 0.0183(16) Uani 1 2 d S T P . .
H4A H 0.5553 0.4132 0.0000 0.022 Uiso 1 2 calc RS T P . .
C5 C 0.6495(2) 0.3778(5) 0.1421(9) 0.0234(15) Uani 1 1 d . . . . .
H5A H 0.6589 0.4074 0.2342 0.028 Uiso 1 1 calc R . . . .
H5B H 0.6615 0.3216 0.1433 0.028 Uiso 1 1 calc R . . . .
C6 C 0.6018(2) 0.3722(5) 0.1411(9) 0.0257(15) Uani 1 1 d . . . . .
H6A H 0.5931 0.3136 0.1401 0.031 Uiso 1 1 calc R . . . .
H6B H 0.5905 0.3986 0.2336 0.031 Uiso 1 1 calc R . . . .
C7 C 0.6457(3) 0.5111(8) 0.0000 0.033(3) Uani 1 2 d DS T P . .
H7 H 0.657(3) 0.538(5) -0.092(6) 0.040 Uiso 1 1 d DR . . . .
C8 C 0.5989(3) 0.5066(7) 0.0000 0.031(3) Uani 1 2 d DS T P . .
H8 H 0.589(3) 0.531(5) -0.097(5) 0.037 Uiso 1 1 d DR . . . .


_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
Bi1 I1 3.1486(7) . ?
Bi1 I2 2.9943(8) . ?
Bi1 I3 3.1762(5) 6 ?
Bi1 I3 3.1762(5) . ?
Bi1 I4 3.006(8) 6 ?
Bi1 I4 3.006(8) . ?
Bi1 I4A 2.99(2) 6 ?
Bi1 I4A 2.99(2) . ?
Bi2 I5 3.1716(7) . ?
Bi2 I7 3.2385(5) 5_756 ?
Bi2 I7 3.2385(5) . ?
Bi2 I8 2.9572(6) . ?
Bi2 I8 2.9571(6) 6_556 ?
Bi2 I6 2.970(5) . ?
Bi2 I6A 3.012(8) . ?
I7 Bi2 3.2385(5) 5_756 ?
N1 C2 1.491(9) . ?
N1 C2 1.491(9) 6_556 ?
N1 C4 1.473(14) . ?
N2 C1 1.493(9) 6_556 ?
N2 C1 1.493(9) . ?
N2 C3 1.467(13) . ?
C1 C2 1.511(10) . ?
C3 C4 1.524(15) . ?
N3 C5 1.493(9) . ?
N3 C5 1.494(9) 6 ?
N3 C7 1.495(14) . ?
N4 C6 1.490(9) 6 ?
N4 C6 1.490(9) . ?
N4 C8 1.496(14) . ?
C5 C6 1.526(9) . ?
C7 C8 1.497(15) . ?

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
I1 Bi1 I3 88.708(14) . 6 ?
I1 Bi1 I3 88.708(14) . . ?
I2 Bi1 I1 178.23(2) . . ?
I2 Bi1 I3 89.996(17) . 6 ?
I2 Bi1 I3 89.996(17) . . ?
I2 Bi1 I4 92.75(14) . . ?
I2 Bi1 I4 92.75(14) . 6 ?
I3 Bi1 I3 85.891(18) 6 . ?
I4 Bi1 I1 88.46(14) . . ?
I4 Bi1 I1 88.46(14) 6 . ?
I4 Bi1 I3 89.98(13) . . ?
I4 Bi1 I3 175.05(10) . 6 ?
I4 Bi1 I3 175.05(10) 6 . ?
I4 Bi1 I3 89.98(13) 6 6 ?
I4 Bi1 I4 94.0(3) . 6 ?
I4A Bi1 I1 91.6(3) . . ?
I4A Bi1 I1 91.6(3) 6 . ?
I4A Bi1 I2 89.7(3) 6 . ?
I4A Bi1 I2 89.7(3) . . ?
I4A Bi1 I3 93.8(3) 6 6 ?
I4A Bi1 I3 93.8(3) . . ?
I4A Bi1 I3 179.5(4) . 6 ?
I4A Bi1 I3 179.5(4) 6 . ?
I4A Bi1 I4A 86.5(6) . 6 ?
I5 Bi2 I7 88.932(12) . 5_756 ?
I5 Bi2 I7 88.932(12) . . ?
I7 Bi2 I7 85.092(19) . 5_756 ?
I8 Bi2 I5 89.072(15) . . ?
I8 Bi2 I5 89.073(15) 6_556 . ?
I8 Bi2 I7 89.658(14) 6_556 . ?
I8 Bi2 I7 89.658(14) . 5_756 ?
I8 Bi2 I7 174.417(18) 6_556 5_756 ?
I8 Bi2 I7 174.417(18) . . ?
I8 Bi2 I8 95.52(2) 6_556 . ?
I8 Bi2 I6 93.92(4) 6_556 . ?
I8 Bi2 I6 93.92(4) . . ?
I8 Bi2 I6A 88.49(7) 6_556 . ?
I8 Bi2 I6A 88.49(7) . . ?
I6 Bi2 I5 175.54(5) . . ?
I6 Bi2 I7 87.78(4) . 5_756 ?
I6 Bi2 I7 87.78(4) . . ?
I6A Bi2 I5 176.38(10) . . ?
I6A Bi2 I7 93.73(7) . 5_756 ?
I6A Bi2 I7 93.73(7) . . ?
Bi2 I7 Bi2 94.908(19) . 5_756 ?
C2 N1 C2 109.6(8) . 6_556 ?
C4 N1 C2 111.1(5) . 6_556 ?
C4 N1 C2 111.1(5) . . ?
C1 N2 C1 109.8(8) 6_556 . ?
C3 N2 C1 110.0(5) . . ?
C3 N2 C1 110.0(5) . 6_556 ?
N2 C1 C2 109.0(6) . . ?
N1 C2 C1 108.4(6) . . ?
N2 C3 C4 109.9(9) . . ?
N1 C4 C3 107.6(9) . . ?
C5 N3 C5 110.1(8) . 6 ?
C5 N3 C7 109.9(5) . . ?
C5 N3 C7 109.9(5) 6 . ?
C6 N4 C6 109.4(8) 6 . ?
C6 N4 C8 110.7(5) 6 . ?
C6 N4 C8 110.7(5) . . ?
N3 C5 C6 108.8(6) . . ?
N4 C6 C5 108.5(6) . . ?
N3 C7 C8 109.6(9) . . ?
N4 C8 C7 108.8(8) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 -0.060 297.4 70.3 ?
2 0.147 0.189 0.500 13.7 0.0 ?
3 0.158 0.797 0.000 12.6 2.1 ?
4 0.342 0.297 0.000 12.6 0.0 ?
5 0.353 0.689 0.500 13.7 2.0 ?
6 0.500 0.000 -0.472 297.4 70.3 ?
7 0.647 0.311 0.500 13.7 0.0 ?
8 0.658 0.703 0.000 12.6 1.9 ?
9 0.842 0.203 0.000 12.6 0.0 ?
10 0.853 0.811 0.500 13.7 2.8 ?


_olex2_submission_special_instructions 'No special instructions were received'
