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

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

data_Compound1_RT
_database_code_depnum_ccdc_archive 'CCDC 1496109'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_date             2016-09-12
_audit_creation_method           'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_chemical_name_systematic        
'1,4-Dipiperazinium iodobismuthate tetrahydrate'
_chemical_formula_iupac          '[NH2(CH2)4NH2][BiI4]2.4H2O'
_chemical_formula_moiety         'Bi I4, 0.5(C4 N2 H12), 2(H2O)'
_chemical_formula_sum            'C2 H10 Bi I4 N O2'
_chemical_formula_weight         796.69

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      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                   7.4697(3)
_cell_length_b                   13.1773(7)
_cell_length_c                   13.9099(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.109(4)
_cell_angle_gamma                90
_cell_volume                     1363.72(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    292.0(2)
_cell_measurement_reflns_used    3660
_cell_measurement_theta_min      4.1240
_cell_measurement_theta_max      30.8960
_cell_oxdiff_length_a            7.4708(3)
_cell_oxdiff_length_b            13.1654(8)
_cell_oxdiff_length_c            13.9224(7)
_cell_oxdiff_angle_alpha         89.873(5)
_cell_oxdiff_angle_beta          95.189(4)
_cell_oxdiff_angle_gamma         89.819(4)
_cell_oxdiff_volume              1363.72(13)
_cell_oxdiff_measurement_reflns_used 3660

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    3.880
_exptl_crystal_F_000             1360.000
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.123
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 -1 -7 0.1821
8 2 10 0.1592
0 3 19 0.1292
-10 0 -1 0.1553
0 -18 3 0.0477
-10 -3 2 0.1640
0 14 -12 0.0570
4 13 -12 0.0890
2 -14 12 0.0899
5 17 -2 0.0952
0 19 -1 0.0703
-5 16 0 0.1216
2 -14 -12 0.0943
8 8 6 0.1410
-1 -1 -19 0.1360
1 -5 19 0.1209
3 -1 -19 0.1018
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
10.0343 -1.3834 -7.4403 -0.0534 0.2997 0.9525
8.4755 1.5506 10.0723 0.1105 -0.5816 0.8059
-0.1131 3.2066 19.2802 0.1832 -0.9830 -0.0091
-10.4172 -0.0357 -1.1298 -0.0288 0.1407 -0.9896
0.4877 -18.2605 3.2372 0.9806 0.1830 0.0706
-10.4279 -2.6275 2.2427 0.1624 0.0277 -0.9863
-0.0227 13.7910 -12.0587 -0.9124 0.3196 -0.0234
3.9743 12.8632 -12.0482 -0.8614 0.3036 0.3574
2.0206 -13.7567 12.0617 0.9127 -0.3369 0.2131
4.9729 16.9990 -2.0692 -0.8905 -0.2603 0.4499
-0.0238 18.9194 -1.0862 -0.9749 -0.3022 -0.0268
-5.0143 15.8576 -0.0804 -0.8072 -0.2519 -0.4965
2.0096 -14.0755 -11.9281 0.4992 0.8187 0.2053
7.9844 8.1886 5.9728 -0.2986 -0.5055 0.7496
-1.0064 -1.2660 -18.9888 -0.2771 0.9419 -0.0996
1.0138 -4.7127 19.0162 0.5795 -0.8313 0.1079
2.9893 -1.1974 -18.9829 -0.2765 0.9074 0.2798
_exptl_absorpt_coefficient_mu    21.950
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.012
_exptl_absorpt_correction_T_max  0.085
_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 1.509
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      292.0(2)
_diffrn_ambient_environment      air
_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            8961
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.3225
_diffrn_reflns_theta_max         31.8949
_diffrn_reflns_theta_full        29.5096
_diffrn_measured_fraction_theta_max 0.8946
_diffrn_measured_fraction_theta_full 0.9957
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.896
_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      0.0009984000
_diffrn_orient_matrix_UB_12      -0.0504978000
_diffrn_orient_matrix_UB_13      0.0179085000
_diffrn_orient_matrix_UB_21      -0.0082447000
_diffrn_orient_matrix_UB_22      -0.0187361000
_diffrn_orient_matrix_UB_23      -0.0479186000
_diffrn_orient_matrix_UB_31      0.0949717000
_diffrn_orient_matrix_UB_32      -0.0012782000
_diffrn_orient_matrix_UB_33      0.0002967000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  50.00   1.00   22.00    --   23.53 -77.00-120.00   91
  2  ω      2.00  30.00   1.00   22.00    --   23.53 -57.00-120.00   28
  3  ω    -22.00   4.00   1.00   22.00    --  -22.90 -77.00-150.00   26
  4  ω     -2.00  90.00   1.00   22.00    --   23.53  77.00  90.00   92
  5  ω    -87.00 -58.00   1.00   22.00    --  -22.90 -77.00-150.00   29
;
_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 99.57
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             4208
_reflns_number_gt                3316
_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.'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.9216P] 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         4208
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.76222(4) 0.02135(3) 0.09119(2) 0.02552(10) Uani 1 1 d . . . . .
I1 I 0.62865(9) 0.18478(5) 0.20378(4) 0.04025(17) Uani 1 1 d . . . . .
I2 I 1.09515(7) 0.15135(5) 0.05719(4) 0.03414(15) Uani 1 1 d . . . . .
I3 I 0.43590(8) -0.11755(5) 0.10341(4) 0.03544(16) Uani 1 1 d . . . . .
I4 I 0.94151(9) -0.08223(6) 0.26239(4) 0.04183(17) Uani 1 1 d . . . . .
N1 N 0.4723(15) 0.0807(9) 0.4335(7) 0.064(3) Uani 1 1 d . . . . .
H1A H 0.5829 0.1055 0.4324 0.077 Uiso 1 1 calc R U . . .
H1B H 0.3994 0.1177 0.3933 0.077 Uiso 1 1 calc R U . . .
C1 C 0.4170(13) 0.0905(8) 0.5300(7) 0.042(2) Uani 1 1 d . . . . .
H1C H 0.2919 0.0707 0.5300 0.050 Uiso 1 1 calc R U . . .
H1D H 0.4271 0.1609 0.5500 0.050 Uiso 1 1 calc R U . . .
C2 C 0.4701(16) -0.0256(10) 0.3988(7) 0.050(3) Uani 1 1 d . . . . .
H2A H 0.5175 -0.0287 0.3361 0.060 Uiso 1 1 calc R U . . .
H2B H 0.3476 -0.0507 0.3918 0.060 Uiso 1 1 calc R U . . .
O1 O 0.8413(12) 0.6651(7) 0.1669(6) 0.067(2) Uani 1 1 d . . . . .
H1O1 H 0.8666 0.6771 0.2276 0.050 Uiso 1 1 d . . . . .
H2O1 H 0.7301 0.6436 0.1627 0.050 Uiso 1 1 d . . . . .
O2 O 0.8474(11) 0.3752(7) 0.9615(6) 0.069(3) Uani 1 1 d . . . . .
H1O2 H 0.9235 0.3411 0.9990 0.050 Uiso 1 1 d . . . . .
H2O2 H 0.7426 0.3560 0.9768 0.050 Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Bi1 0.02791(15) 0.02338(19) 0.02534(15) -0.00027(12) 0.00277(11) -0.00083(13)
I1 0.0521(4) 0.0311(4) 0.0383(3) -0.0076(3) 0.0081(3) 0.0080(3)
I2 0.0323(3) 0.0281(3) 0.0430(3) -0.0073(3) 0.0087(2) -0.0055(2)
I3 0.0359(3) 0.0359(4) 0.0340(3) 0.0130(3) 0.0001(2) -0.0094(3)
I4 0.0482(4) 0.0375(4) 0.0374(3) 0.0063(3) -0.0090(3) 0.0048(3)
N1 0.082(7) 0.055(8) 0.054(6) 0.008(5) -0.004(5) 0.014(6)
C1 0.051(6) 0.031(6) 0.043(5) -0.008(4) 0.004(4) 0.008(5)
C2 0.066(7) 0.050(8) 0.032(5) -0.006(5) -0.001(5) -0.006(6)
O1 0.081(6) 0.058(7) 0.057(5) -0.006(4) -0.020(4) -0.001(5)
O2 0.061(5) 0.057(7) 0.089(6) 0.010(5) 0.001(5) 0.022(5)

_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 2.8922(7) . ?
Bi1 I4 2.9597(7) . ?
Bi1 I3 3.0650(7) . ?
Bi1 I2 3.0906(7) . ?
Bi1 I3 3.2265(6) 3_655 ?
Bi1 I2 3.3113(7) 3_755 ?
I2 Bi1 3.3113(7) 3_755 ?
I3 Bi1 3.2265(6) 3_655 ?
N1 C1 1.446(13) . ?
N1 C2 1.480(15) . ?
C1 C2 1.508(15) 3_656 ?
C2 C1 1.508(15) 3_656 ?

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 I4 93.49(2) . . ?
I1 Bi1 I3 95.75(2) . . ?
I4 Bi1 I3 89.146(19) . . ?
I1 Bi1 I2 89.50(2) . . ?
I4 Bi1 I2 93.79(2) . . ?
I3 Bi1 I2 173.824(19) . . ?
I1 Bi1 I3 90.41(2) . 3_655 ?
I4 Bi1 I3 175.62(2) . 3_655 ?
I3 Bi1 I3 88.481(17) . 3_655 ?
I2 Bi1 I3 88.229(17) . 3_655 ?
I1 Bi1 I2 174.22(2) . 3_755 ?
I4 Bi1 I2 92.12(2) . 3_755 ?
I3 Bi1 I2 85.744(18) . 3_755 ?
I2 Bi1 I2 88.717(18) . 3_755 ?
I3 Bi1 I2 84.036(18) 3_655 3_755 ?
Bi1 I2 Bi1 91.284(18) . 3_755 ?
Bi1 I3 Bi1 91.518(17) . 3_655 ?
C1 N1 C2 113.1(9) . . ?
N1 C1 C2 111.7(8) . 3_656 ?
N1 C2 C1 109.4(8) . 3_656 ?

_refine_diff_density_max         3.222
_refine_diff_density_min         -3.520
_refine_diff_density_rms         0.341

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7


TITL e16mtw030 in P2(1)/c
CELL  0.71073   7.4697  13.1773  13.9099   90.000   95.109   90.000
ZERR     3.00   0.0003   0.0007   0.0006    0.000    0.004    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    N    O    I    BI   H
UNIT  8 4 8 16 4 40
MERG   2
FMAP   2
PLAN   20
ACTA
BOND
L.S.   4
WGHT    0.047200    0.921600
FVAR       1.60862
BI1   5    0.762225    0.021349    0.091186    11.00000    0.02791    0.02338 =
         0.02534   -0.00027    0.00277   -0.00083
I1    4    0.628648    0.184784    0.203780    11.00000    0.05205    0.03115 =
         0.03827   -0.00758    0.00810    0.00797
I2    4    1.095145    0.151345    0.057192    11.00000    0.03231    0.02806 =
         0.04301   -0.00725    0.00868   -0.00553
I3    4    0.435899   -0.117549    0.103405    11.00000    0.03588    0.03592 =
         0.03396    0.01302    0.00010   -0.00937
I4    4    0.941513   -0.082232    0.262395    11.00000    0.04823    0.03755 =
         0.03743    0.00628   -0.00898    0.00475
N1    2    0.472267    0.080653    0.433462    11.00000    0.08204    0.05471 =
         0.05431    0.00781   -0.00359    0.01352
AFIX  23
H1A   6    0.582889    0.105466    0.432400    11.00000   -1.20000
H1B   6    0.399395    0.117650    0.393286    11.00000   -1.20000
AFIX   0
C1    1    0.416982    0.090460    0.530014    11.00000    0.05056    0.03148 =
         0.04274   -0.00803    0.00439    0.00837
AFIX  23
H1C   6    0.291901    0.070660    0.529961    11.00000   -1.20000
H1D   6    0.427085    0.160912    0.549972    11.00000   -1.20000
AFIX   0
C2    1    0.470136   -0.025551    0.398771    11.00000    0.06608    0.05046 =
         0.03188   -0.00639   -0.00117   -0.00597
AFIX  23
H2A   6    0.517545   -0.028652    0.336144    11.00000   -1.20000
H2B   6    0.347640   -0.050728    0.391844    11.00000   -1.20000
AFIX   0
O1    3    0.841341    0.665112    0.166894    11.00000    0.08144    0.05809 =
         0.05729   -0.00563   -0.02050   -0.00134
AFIX   1
H1O1  6    0.866610    0.677060    0.227580    11.00000    0.05000
H2O1  6    0.730080    0.643590    0.162740    11.00000    0.05000
AFIX   0
O2    3    0.847361    0.375214    0.961526    11.00000    0.06129    0.05673 =
         0.08863    0.00985    0.00127    0.02227
AFIX   1
H1O2  6    0.923450    0.341070    0.998980    11.00000    0.05000
H2O2  6    0.742620    0.355980    0.976770    11.00000    0.05000
AFIX   0
HKLF    4

REM  e16mtw030 in P2(1)/c
REM R1 =  0.0452 for    3316 Fo > 4sig(Fo)  and  0.0634 for all    4208 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0478      0.2418

REM Highest difference peak  3.222,  deepest hole -3.520,  1-sigma level  0.341
Q1    1   0.7592  0.0844  0.0849  11.00000  0.05    3.22
Q2    1   0.7631 -0.0412  0.0984  11.00000  0.05    2.86
Q3    1   0.8520  0.0215  0.1372  11.00000  0.05    1.76
Q4    1   0.3165  0.0276  0.4533  11.00000  0.05    1.75
Q5    1   0.6167  0.1227  0.2047  11.00000  0.05    1.73
Q6    1   1.0852  0.2179  0.0565  11.00000  0.05    1.50
Q7    1   0.4308 -0.1825  0.1051  11.00000  0.05    1.43
Q8    1   0.8501  0.1027  0.1152  11.00000  0.05    1.38
Q9    1   0.6329  0.1040  0.0591  11.00000  0.05    1.38
Q10   1   0.9525 -0.0161  0.2664  11.00000  0.05    1.37
Q11   1   0.6497  0.0220  0.0422  11.00000  0.05    1.35
Q12   1   1.0960  0.0882  0.0579  11.00000  0.05    1.35
Q13   1   0.4357 -0.0529  0.1012  11.00000  0.05    1.31
Q14   1   0.7332  0.0190  0.1470  11.00000  0.05    1.31
Q15   1   0.6222  0.2542  0.2026  11.00000  0.05    1.26
Q16   1   0.9297 -0.1477  0.2619  11.00000  0.05    1.20
Q17   1   0.7937  0.1416  0.0449  11.00000  0.05    1.12
Q18   1   0.9829  0.1244  0.0963  11.00000  0.05    1.09
Q19   1   0.5614 -0.2030  0.1329  11.00000  0.05    1.08
Q20   1   0.6962  0.2605  0.2248  11.00000  0.05    1.04
;
_shelx_res_checksum              85964


# start Validation Reply Form
_vrf_PLAT417_NH2CH24NH2BiI42.4H2O_RT_Compound1 
;
PROBLEM: Short Inter D-H..H-D       H1A    ..  H2O2    ..       1.39 Ang.  
RESPONSE: Water hydrogen positions not accurately modelled in structure and therefore the interatomic H-H distances calculated are likely incorrect 
;
_vrf_PLAT241_NH2CH24NH2BiI42.4H2O_RT_Compound1 
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         N1 Check 
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher, tied with greater thermal motion at RT data collection giving a high Ueq for N1
;
_vrf_PLAT245_NH2CH24NH2BiI42.4H2O_RT_Compound1 
;
PROBLEM: U(iso) H1O1    Smaller than U(eq) O1      by ...      0.017 AngSq 
RESPONSE: Hydrogen positions in the structure have fixed U, not free to refine
;
_vrf_PLAT342_NH2CH24NH2BiI42.4H2O_RT_Compound1 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.015 Ang.  
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher, tied with greater thermal motion at RT data collection giving a high Ueq for N1
;
# 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_Compound1_150K
_database_code_depnum_ccdc_archive 'CCDC 1496110'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_date             2016-09-12
_audit_creation_method           'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_chemical_name_systematic        
'1,4-Dipiperazinium iodobismuthate tetrahydrate'
_chemical_formula_iupac          '[NH2(CH2)4NH2][BiI4]2.4H2O'
_chemical_formula_moiety         'Bi I4, 0.5(C4 N2 H12), 2(H2O)'
_chemical_formula_sum            'C2 H10 Bi I4 N O2'
_chemical_formula_weight         796.69

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                   7.3508(2)
_cell_length_b                   13.0215(4)
_cell_length_c                   13.9875(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.588(2)
_cell_angle_gamma                90
_cell_volume                     1334.57(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    8034
_cell_measurement_theta_min      4.1550
_cell_measurement_theta_max      31.7500
_cell_oxdiff_length_a            7.3494(3)
_cell_oxdiff_length_b            13.0194(6)
_cell_oxdiff_length_c            13.9916(5)
_cell_oxdiff_angle_alpha         90.005(3)
_cell_oxdiff_angle_beta          94.550(3)
_cell_oxdiff_angle_gamma         89.951(4)
_cell_oxdiff_volume              1334.57(10)
_cell_oxdiff_measurement_reflns_used 8034

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    3.965
_exptl_crystal_F_000             1360.0
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.114
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 15 -12 0.1118
0 13 14 0.0513
10 2 -4 0.1388
-10 2 0 0.3602
10 -2 -2 0.1208
0 -16 10 0.1035
0 -17 -7 0.0551
-1 -14 -13 0.0570
1 -14 -13 0.0516
5 -11 -13 0.0834
0 -2 -20 0.0903
-3 7 -17 0.1320
-3 15 -9 0.1400
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
0.2174 14.5698 -11.9864 0.7169 -0.6783 0.1609
0.1298 12.5060 14.3717 0.7590 0.6495 -0.0461
9.9798 1.9982 -4.0002 0.0434 0.0077 0.9765
-9.9800 1.9954 0.0067 0.1492 -0.2303 -0.9329
9.9797 -1.9951 -2.0035 -0.1608 0.1305 0.9473
-0.0001 -15.9733 9.9839 -0.8053 0.5911 -0.1310
-0.0023 -16.9686 -6.9891 -0.9578 -0.2519 -0.0118
-1.0008 -13.9730 -12.9788 -0.8266 -0.5905 -0.0514
0.9953 -13.9728 -12.9802 -0.8348 -0.5467 0.1366
4.9876 -10.9777 -12.9828 -0.6895 -0.4764 0.5237
-0.0026 -1.9930 -19.9682 -0.2238 -0.9870 0.1373
-2.9956 6.9902 -16.9709 0.2916 -0.9545 -0.1334
-2.9939 14.9746 -8.9835 0.7696 -0.6010 -0.1619
_exptl_absorpt_coefficient_mu    22.429
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.053
_exptl_absorpt_correction_T_max  0.337
_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 0.782
_oxdiff_exptl_absorpt_empirical_full_max 1.464
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.01(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            16574
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.3147
_diffrn_reflns_theta_max         32.1539
_diffrn_reflns_theta_full        29.5096
_diffrn_measured_fraction_theta_max 0.9139
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.915
_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      -0.0041415000
_diffrn_orient_matrix_UB_12      0.0540514000
_diffrn_orient_matrix_UB_13      0.0058143000
_diffrn_orient_matrix_UB_21      0.0219621000
_diffrn_orient_matrix_UB_22      -0.0057524000
_diffrn_orient_matrix_UB_23      0.0499978000
_diffrn_orient_matrix_UB_31      0.0942012000
_diffrn_orient_matrix_UB_32      0.0036695000
_diffrn_orient_matrix_UB_33      -0.0072543000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  41.00   1.00    4.00    --  -22.24  38.00 -30.00   77
  2  ω     13.00  38.00   1.00    4.00    --  -22.24  57.00-120.00   25
  3  ω     -4.00  34.00   1.00    4.00    --   22.86  77.00 -60.00   38
  4  ω      6.00  83.00   1.00    4.00    --   22.86  57.00  30.00   77
  5  ω     14.00  85.00   1.00    4.00    --   22.86  57.00  90.00   71
  6  ω     -4.00  90.00   1.00    4.00    --   22.86  77.00 150.00   94
  7  ω    -25.00  50.00   1.00    4.00    --   22.86 -77.00-150.00   75
  8  ω     34.00  60.00   1.00    4.00    --   22.86-178.00-150.00   26
;
_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 99.77
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             4290
_reflns_number_gt                3840
_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.'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)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         4290
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 0.76054(3) 0.51983(2) 0.59107(2) 0.01050(7) Uani 1 1 d . . . . .
I2 I 0.42953(6) 0.37919(4) 0.60151(3) 0.01509(10) Uani 1 1 d . . . . .
I3 I 1.09782(6) 0.65230(4) 0.55958(3) 0.01463(10) Uani 1 1 d . . . . .
I4 I 0.62345(6) 0.68409(4) 0.70439(3) 0.01693(11) Uani 1 1 d . . . . .
I1 I 0.93848(6) 0.41408(4) 0.76105(3) 0.01808(11) Uani 1 1 d . . . . .
N1 N 0.5262(8) 1.0820(5) 0.5673(4) 0.0181(13) Uani 1 1 d . . . . .
H1A H 0.5982 1.1195 0.6078 0.022 Uiso 1 1 calc R U . . .
H1B H 0.4133 1.1067 0.5675 0.022 Uiso 1 1 calc R U . . .
C1 C 0.4117(10) 0.9080(6) 0.5303(5) 0.0192(15) Uani 1 1 d . . . . .
H1C H 0.4200 0.8368 0.5505 0.023 Uiso 1 1 calc R U . . .
H1D H 0.2850 0.9291 0.5298 0.023 Uiso 1 1 calc R U . . .
C2 C 0.5284(10) 0.9744(6) 0.6008(5) 0.0173(15) Uani 1 1 d . . . . .
H2A H 0.4816 0.9708 0.6636 0.021 Uiso 1 1 calc R U . . .
H2B H 0.6528 0.9489 0.6064 0.021 Uiso 1 1 calc R U . . .
O1 O 0.8461(8) 0.1582(5) 0.6656(4) 0.0277(13) Uani 1 1 d . . . . .
H1O1 H 0.8737 0.2111 0.7009 0.050 Uiso 1 1 d . . . . .
H2O1 H 0.8425 0.1073 0.7050 0.050 Uiso 1 1 d . . . . .
O2 O 0.8449(7) 0.8737(5) 0.4609(4) 0.0291(13) Uani 1 1 d . . . . .
H1O2 H 0.8914 0.8238 0.4948 0.050 Uiso 1 1 d . . . . .
H2O2 H 0.9348 0.9127 0.4490 0.050 Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Bi1 0.01259(12) 0.00945(13) 0.00932(12) -0.00047(9) 0.00012(9) -0.00058(8)
I2 0.0166(2) 0.0146(2) 0.0136(2) 0.00569(17) -0.00136(16) -0.00437(16)
I3 0.0143(2) 0.0115(2) 0.0183(2) -0.00405(17) 0.00302(16) -0.00272(16)
I4 0.0235(2) 0.0132(2) 0.0142(2) -0.00378(17) 0.00233(17) 0.00343(17)
I1 0.0221(2) 0.0153(2) 0.0157(2) 0.00324(18) -0.00495(17) 0.00237(18)
N1 0.019(3) 0.020(3) 0.015(3) -0.008(3) 0.000(2) 0.000(2)
C1 0.025(4) 0.014(4) 0.018(3) 0.000(3) 0.001(3) -0.008(3)
C2 0.020(3) 0.019(4) 0.013(3) 0.000(3) 0.000(3) 0.001(3)
O1 0.034(3) 0.018(3) 0.029(3) 0.002(3) -0.009(2) -0.001(3)
O2 0.023(3) 0.028(4) 0.036(3) -0.002(3) 0.000(2) 0.005(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 I4 2.8911(5) . ?
Bi1 I1 2.9602(5) . ?
Bi1 I2 3.0581(5) . ?
Bi1 I3 3.0807(5) . ?
Bi1 I2 3.2148(5) 3_666 ?
Bi1 I3 3.3013(5) 3_766 ?
I2 Bi1 3.2148(5) 3_666 ?
I3 Bi1 3.3014(5) 3_766 ?
N1 C2 1.477(10) . ?
N1 C1 1.480(9) 3_676 ?
C1 N1 1.480(9) 3_676 ?
C1 C2 1.523(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
I4 Bi1 I1 93.142(15) . . ?
I4 Bi1 I2 95.928(15) . . ?
I1 Bi1 I2 89.154(14) . . ?
I4 Bi1 I3 89.080(14) . . ?
I1 Bi1 I3 93.806(14) . . ?
I2 Bi1 I3 174.041(14) . . ?
I4 Bi1 I2 90.550(14) . 3_666 ?
I1 Bi1 I2 176.176(16) . 3_666 ?
I2 Bi1 I2 89.473(13) . 3_666 ?
I3 Bi1 I2 87.246(13) . 3_666 ?
I4 Bi1 I3 173.606(15) . 3_766 ?
I1 Bi1 I3 93.165(14) . 3_766 ?
I2 Bi1 I3 85.221(13) . 3_766 ?
I3 Bi1 I3 89.448(13) . 3_766 ?
I2 Bi1 I3 83.164(13) 3_666 3_766 ?
Bi1 I2 Bi1 90.528(13) . 3_666 ?
Bi1 I3 Bi1 90.551(13) . 3_766 ?
C2 N1 C1 112.3(6) . 3_676 ?
N1 C1 C2 110.4(6) 3_676 . ?
N1 C2 C1 110.0(6) . . ?

_refine_diff_density_max         1.996
_refine_diff_density_min         -3.526
_refine_diff_density_rms         0.519

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7


TITL e16mtw006 in P2(1)/c
CELL  0.71073   7.3508  13.0215  13.9875   90.000   94.588   90.000
ZERR     3.00   0.0002   0.0004   0.0003    0.000    0.002    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    N    I    BI   O    H
UNIT  8 4 16 4 8 40
MERG   2
FMAP   2
PLAN   20
ACTA
BOND
L.S.   4
WGHT    0.036400
FVAR       1.67103
BI1   4    0.760542    0.519827    0.591071    11.00000    0.01259    0.00945 =
         0.00932   -0.00047    0.00012   -0.00058
I2    3    0.429528    0.379195    0.601509    11.00000    0.01664    0.01460 =
         0.01362    0.00569   -0.00136   -0.00437
I3    3    1.097816    0.652298    0.559578    11.00000    0.01433    0.01150 =
         0.01835   -0.00405    0.00302   -0.00272
I4    3    0.623447    0.684086    0.704387    11.00000    0.02354    0.01320 =
         0.01418   -0.00378    0.00233    0.00343
I1    3    0.938478    0.414078    0.761052    11.00000    0.02215    0.01534 =
         0.01571    0.00324   -0.00495    0.00237
N1    2    0.526205    1.081997    0.567313    11.00000    0.01903    0.01950 =
         0.01545   -0.00783   -0.00007    0.00008
AFIX  23
H1A   6    0.598191    1.119520    0.607840    11.00000   -1.20000
H1B   6    0.413320    1.106661    0.567518    11.00000   -1.20000
AFIX   0
C1    1    0.411664    0.908039    0.530321    11.00000    0.02545    0.01389 =
         0.01811   -0.00030    0.00144   -0.00785
AFIX  23
H1C   6    0.419964    0.836802    0.550474    11.00000   -1.20000
H1D   6    0.285030    0.929131    0.529804    11.00000   -1.20000
AFIX   0
C2    1    0.528423    0.974359    0.600800    11.00000    0.01964    0.01858 =
         0.01349   -0.00029    0.00010    0.00147
AFIX  23
H2A   6    0.481553    0.970808    0.663601    11.00000   -1.20000
H2B   6    0.652805    0.948858    0.606361    11.00000   -1.20000
AFIX   0
O1    5    0.846080    0.158226    0.665609    11.00000    0.03379    0.01847 =
         0.02893    0.00207   -0.00857   -0.00136
AFIX   1
H1O1  6    0.873730    0.211090    0.700950    11.00000    0.05000
H2O1  6    0.842480    0.107300    0.704970    11.00000    0.05000
AFIX   0
O2    5    0.844901    0.873733    0.460926    11.00000    0.02277    0.02823 =
         0.03602   -0.00177    0.00038    0.00488
AFIX   1
H1O2  6    0.891440    0.823780    0.494770    11.00000    0.05000
H2O2  6    0.934840    0.912660    0.448970    11.00000    0.05000
AFIX   0
HKLF    4

REM  e16mtw006 in P2(1)/c
REM R1 =  0.0382 for    3840 Fo > 4sig(Fo)  and  0.0445 for all    4290 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0357      0.0000

REM Highest difference peak  1.994,  deepest hole -3.509,  1-sigma level  0.519
Q1    1   0.6341  0.5201  0.5793  11.00000  0.05    1.99
Q2    1   0.8867  0.4764  0.5418  11.00000  0.05    1.78
Q3    1   0.5269  1.2153  0.6472  11.00000  0.05    1.66
Q4    1   0.7854  0.5756  0.5437  11.00000  0.05    1.65
Q5    1   0.8823  0.5185  0.5759  11.00000  0.05    1.61
Q6    1   0.9576  0.4992  0.5035  11.00000  0.05    1.57
Q7    1   1.3142  0.5984  0.6625  11.00000  0.05    1.54
Q8    1   0.2848  0.3815  0.5977  11.00000  0.05    1.53
Q9    1   0.5964  0.7340  0.6594  11.00000  0.05    1.50
Q10   1   0.8816  0.7389  0.6909  11.00000  0.05    1.44
Q11   1   0.5199  0.4775  0.6292  11.00000  0.05    1.42
Q12   1   1.1190  0.6447  0.4452  11.00000  0.05    1.40
Q13   1   1.1117  0.5813  0.4836  11.00000  0.05    1.39
Q14   1   0.5458  0.8380  0.6610  11.00000  0.05    1.39
Q15   1   0.5639  0.3759  0.6009  11.00000  0.05    1.37
Q16   1   0.7584  0.4649  0.6376  11.00000  0.05    1.36
Q17   1   0.8428  0.3643  0.6494  11.00000  0.05    1.35
Q18   1   0.7478  0.5795  0.6350  11.00000  0.05    1.34
Q19   1   1.2915  0.6885  0.6773  11.00000  0.05    1.33
Q20   1   0.5679  0.4775  0.6440  11.00000  0.05    1.32
;
_shelx_res_checksum              18637

# start Validation Reply Form
_vrf_PLAT342_shelx               
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01 Ang.
RESPONSE: Heavy atom structure - Errors on light atom bond lengths will be higher
;
# 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_Compound2_RT
_database_code_depnum_ccdc_archive 'CCDC 1496111'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_date             2016-09-12
_audit_creation_method           'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_chemical_name_systematic        
'1-Methyl-1,4-Dipiperazinium iodobismuthate trihydrate'
_chemical_formula_iupac          '[CH3NH(CH2)4NH2][BiI4]2.3H2O'
_chemical_formula_moiety         'Bi2 I8, (C5 N2 H14), 3(H2O)'
_chemical_formula_sum            'C5 H20 Bi2 I8 N2 O3'
_chemical_formula_weight         1589.2696

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      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                   7.6488(4)
_cell_length_b                   13.1532(8)
_cell_length_c                   13.7033(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.481(5)
_cell_angle_gamma                90
_cell_volume                     1369.83(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    292.23(10)
_cell_measurement_reflns_used    3426
_cell_measurement_theta_min      4.0740
_cell_measurement_theta_max      31.0430
_cell_oxdiff_length_a            7.6492(3)
_cell_oxdiff_length_b            13.1480(9)
_cell_oxdiff_length_c            13.7094(7)
_cell_oxdiff_angle_alpha         89.974(5)
_cell_oxdiff_angle_beta          96.531(4)
_cell_oxdiff_angle_gamma         90.058(4)
_cell_oxdiff_volume              1369.82(13)
_cell_oxdiff_measurement_reflns_used 3426

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    3.804
_exptl_crystal_F_000             1316
_exptl_crystal_size_max          0.413
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.176
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-11 -1 0 0.2034
0 13 -14 0.0762
0 -13 14 0.0932
1 -13 -13 0.1010
11 0 -1 0.2023
0 -18 -1 0.1007
0 1 19 0.0819
0 10 16 0.0611
0 17 8 0.0649
-11 1 1 0.1963
2 16 -9 0.1047
1 3 -19 0.1122
0 -3 -19 0.1148
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
-10.7074 -1.2211 0.2903 0.0031 0.0189 0.9998
-0.2316 12.7508 -13.8805 -0.0249 -0.9975 0.0657
-0.1332 -12.8053 13.9045 0.0250 0.9992 -0.0317
0.5172 -13.3687 -13.3812 0.9975 -0.0249 0.0661
10.7703 -0.1578 -1.2348 0.0847 -0.0047 -0.9964
-0.0070 -18.0338 -0.9967 0.7508 0.6183 0.0569
0.0229 1.0179 18.9460 -0.6986 0.6899 -0.1139
0.0222 10.0318 15.9543 -0.9526 0.2470 -0.1219
0.0150 17.0379 7.9769 -0.9537 -0.3142 -0.0949
-10.9926 0.9791 1.0265 -0.1108 -0.0340 1.0160
1.9935 16.0259 -8.9801 -0.3179 -0.9211 -0.1790
0.9779 2.9916 -18.9487 0.5427 -0.8325 0.0094
-0.0235 -3.0216 -18.9459 0.7781 -0.6169 0.1196
_exptl_absorpt_coefficient_mu    43.639
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.006
_exptl_absorpt_correction_T_max  0.040
_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 0.636
_oxdiff_exptl_absorpt_empirical_full_max 1.554
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_diffrn_ambient_temperature      292.23(10)
_diffrn_ambient_environment      air
_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            8333
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.3042
_diffrn_reflns_theta_max         32.0057
_diffrn_measured_fraction_theta_max 0.8819
_diffrn_reflns_theta_full        29.5096
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.882
_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      0.0033010000
_diffrn_orient_matrix_UB_12      -0.0397127000
_diffrn_orient_matrix_UB_13      -0.0347416000
_diffrn_orient_matrix_UB_21      0.0034315000
_diffrn_orient_matrix_UB_22      -0.0364058000
_diffrn_orient_matrix_UB_23      0.0383656000
_diffrn_orient_matrix_UB_31      -0.0932134000
_diffrn_orient_matrix_UB_32      -0.0027985000
_diffrn_orient_matrix_UB_33      -0.0057488000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -10.00   1.00   15.00    --  -22.90 -38.00 150.00   41
  2  ω    -80.00  -1.00   1.00   15.00    --  -22.90 -77.00 120.00   79
  3  ω      8.00  93.00   1.00   15.00    --   23.69  38.00  30.00   85
  4  ω     25.00  63.00   1.00   15.00    --   23.69 -99.00 -90.00   38
;
_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     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             4206
_reflns_number_gt                3350
_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.'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4206
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.26676(3) 0.98155(2) 0.09163(2) 0.02678(9) Uani 1 1 d . . . . .
I1 I 0.43980(9) 1.08906(6) 0.26417(5) 0.0547(2) Uani 1 1 d . . . . .
I2 I -0.05799(7) 1.11444(5) 0.10565(4) 0.03796(15) Uani 1 1 d . . . . .
I3 I 0.59305(7) 0.85038(4) 0.05931(4) 0.03815(15) Uani 1 1 d . . . . .
I4 I 0.14126(9) 0.81513(5) 0.20438(5) 0.04700(17) Uani 1 1 d . . . . .
C1 C 0.9186(16) 0.5909(10) 0.0351(8) 0.065(3) Uani 1 1 d . . . . .
C2 C 0.766(4) 0.624(3) -0.131(3) 0.107(12) Uani 0.5 1 d . . P . .
C3 C 1.0413(17) 0.5243(9) 0.1032(8) 0.062(3) Uani 1 1 d . . . . .
N1 N 0.943(3) 0.5815(17) -0.0661(14) 0.078(7) Uani 0.5 1 d . . P . .
N2 N 0.829(2) 0.5336(13) -0.0455(15) 0.052(5) Uani 0.5 1 d . . P . .
O1 O 0.3432(13) 0.6280(9) 0.9619(8) 0.112(4) Uani 1 1 d . . . . .
H1O1 H 0.3153 0.6799 0.9994 0.050 Uiso 1 1 d . . . . .
H2O1 H 0.2592 0.5850 0.9682 0.050 Uiso 1 1 d . . . . .
O2 O 0.657(3) 0.6623(13) -0.1658(12) 0.075(5) Uani 0.5 1 d . . P . .
H1O2 H 0.6166 0.7045 -0.2111 0.050 Uiso 0.5 1 d . . P . .
H2O2 H 0.5621 0.6414 -0.1407 0.050 Uiso 0.5 1 d . . P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Bi1 0.03088(15) 0.02477(16) 0.02474(14) 0.00083(12) 0.00326(10) 0.00041(12)
I1 0.0579(4) 0.0582(5) 0.0444(4) -0.0176(3) -0.0108(3) -0.0080(3)
I2 0.0413(3) 0.0384(3) 0.0332(3) -0.0140(3) 0.0000(2) 0.0111(3)
I3 0.0376(3) 0.0309(3) 0.0477(3) 0.0124(3) 0.0126(2) 0.0073(2)
I4 0.0617(4) 0.0343(3) 0.0466(4) 0.0132(3) 0.0127(3) -0.0074(3)
C1 0.086(8) 0.065(8) 0.043(6) -0.010(6) 0.005(6) 0.021(7)
C2 0.076(18) 0.12(3) 0.12(3) -0.01(2) -0.045(18) 0.037(19)
C3 0.093(9) 0.041(6) 0.050(6) -0.010(5) 0.005(6) 0.006(6)
N1 0.12(2) 0.059(14) 0.046(11) 0.001(11) -0.007(12) 0.028(14)
N2 0.052(10) 0.033(10) 0.067(12) -0.008(9) -0.004(9) -0.010(8)
O1 0.127(8) 0.113(9) 0.098(8) -0.027(7) 0.019(7) -0.075(8)
O2 0.120(15) 0.049(10) 0.051(9) 0.006(9) -0.013(9) -0.007(11)

_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 I4 2.9044(7) . ?
Bi1 I1 2.9386(7) . ?
Bi1 I2 3.0610(6) . ?
Bi1 I3 3.1066(6) . ?
Bi1 I2 3.2369(6) 3_575 ?
Bi1 I3 3.2886(6) 3_675 ?
I2 Bi1 3.2370(6) 3_575 ?
I3 Bi1 3.2887(6) 3_675 ?
C1 N1 1.43(2) . ?
C1 N2 1.44(2) . ?
C1 C3 1.523(17) . ?
C2 O2 1.05(3) . ?
C2 N1 1.63(3) . ?
C2 N2 1.69(4) . ?
C3 N1 1.49(2) 3_765 ?
C3 N2 1.54(2) 3_765 ?
N1 N2 1.14(3) . ?
N1 C3 1.49(2) 3_765 ?
N2 C3 1.54(2) 3_765 ?

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 Bi1 I1 94.62(2) . . ?
I4 Bi1 I2 94.46(2) . . ?
I1 Bi1 I2 88.26(2) . . ?
I4 Bi1 I3 88.644(19) . . ?
I1 Bi1 I3 94.92(2) . . ?
I2 Bi1 I3 175.368(18) . . ?
I4 Bi1 I2 89.36(2) . 3_575 ?
I1 Bi1 I2 174.05(2) . 3_575 ?
I2 Bi1 I2 87.010(16) . 3_575 ?
I3 Bi1 I2 89.590(17) . 3_575 ?
I4 Bi1 I3 172.76(2) . 3_675 ?
I1 Bi1 I3 91.91(2) . 3_675 ?
I2 Bi1 I3 88.862(17) . 3_675 ?
I3 Bi1 I3 87.674(16) . 3_675 ?
I2 Bi1 I3 84.380(17) 3_575 3_675 ?
Bi1 I2 Bi1 92.989(16) . 3_575 ?
Bi1 I3 Bi1 92.326(16) . 3_675 ?
N1 C1 N2 46.7(11) . . ?
N1 C1 C3 114.0(12) . . ?
N2 C1 C3 112.0(12) . . ?
O2 C2 N1 170(4) . . ?
O2 C2 N2 144(4) . . ?
N1 C2 N2 40.0(12) . . ?
N1 C3 C1 113.3(12) 3_765 . ?
N1 C3 N2 44.1(10) 3_765 3_765 ?
C1 C3 N2 111.0(11) . 3_765 ?
N2 N1 C1 67.5(16) . . ?
N2 N1 C3 70.1(17) . 3_765 ?
C1 N1 C3 115.9(17) . 3_765 ?
N2 N1 C2 73(2) . . ?
C1 N1 C2 108(2) . . ?
C3 N1 C2 103(2) 3_765 . ?
N1 N2 C1 65.8(15) . . ?
N1 N2 C3 65.8(15) . 3_765 ?
C1 N2 C3 111.9(13) . 3_765 ?
N1 N2 C2 66.9(18) . . ?
C1 N2 C2 103.5(17) . . ?
C3 N2 C2 98.2(17) 3_765 . ?

_refine_diff_density_max         1.431
_refine_diff_density_min         -2.822
_refine_diff_density_rms         0.416

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7

TITL e16mtw031 in P2(1)/c
CELL  0.71073   7.6488  13.1532  13.7033   90.000   96.481   90.000
ZERR     4.00   0.0004   0.0008   0.0007    0.000    0.005    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    N    O    I    BI   H
UNIT  10 4 6 16 4 4
MERG   2
FMAP   2
PLAN   20
ACTA
BOND
L.S.   4
WGHT    0.040500
FVAR       1.77520
BI1   5    0.266758    0.981553    0.091627    11.00000    0.03088    0.02477 =
         0.02474    0.00083    0.00326    0.00041
I1    4    0.439796    1.089064    0.264171    11.00000    0.05785    0.05816 =
         0.04442   -0.01761   -0.01084   -0.00801
I2    4   -0.057985    1.114443    0.105646    11.00000    0.04126    0.03844 =
         0.03322   -0.01404   -0.00001    0.01109
I3    4    0.593049    0.850383    0.059309    11.00000    0.03757    0.03093 =
         0.04773    0.01240    0.01260    0.00727
I4    4    0.141263    0.815130    0.204384    11.00000    0.06166    0.03431 =
         0.04655    0.01320    0.01274   -0.00735
C1    1    0.918648    0.590869    0.035103    11.00000    0.08596    0.06452 =
         0.04345   -0.00977    0.00529    0.02130
C2    1    0.766072    0.623709   -0.130539    10.50000    0.07612    0.11550 =
         0.11613   -0.00874   -0.04492    0.03666
C3    1    1.041312    0.524292    0.103166    11.00000    0.09312    0.04122 =
         0.05015   -0.00984    0.00536    0.00572
N1    2    0.943191    0.581489   -0.066103    10.50000    0.12467    0.05909 =
         0.04586    0.00141   -0.00651    0.02784
N2    2    0.829097    0.533554   -0.045505    10.50000    0.05236    0.03328 =
         0.06672   -0.00762   -0.00424   -0.01037
O1    3    0.343175    0.627961    0.961885    11.00000    0.12721    0.11348 =
         0.09758   -0.02702    0.01900   -0.07456
AFIX   1
H1O1  6    0.315250    0.679910    0.999410    11.00000    0.05000
H2O1  6    0.259180    0.584980    0.968240    11.00000    0.05000
AFIX   0
O2    3    0.656986    0.662290   -0.165808    10.50000    0.11995    0.04892 =
         0.05099    0.00616   -0.01304   -0.00695
AFIX   1
H1O2  6    0.616580    0.704500   -0.211070    10.50000    0.05000
H2O2  6    0.562060    0.641420   -0.140660    10.50000    0.05000
AFIX   0
HKLF    4

REM  e16mtw031 in P2(1)/c
REM R1 =  0.0429 for    3350 Fo > 4sig(Fo)  and  0.0591 for all    4206 data
REM    109 parameters refined using      0 restraints

END

WGHT      0.0413      0.0000

REM Highest difference peak  1.431,  deepest hole -2.822,  1-sigma level  0.416
Q1    1   0.4720  0.9591 -0.0381  11.00000  0.05    1.43
Q2    1   0.1997  0.9797 -0.0026  11.00000  0.05    1.29
Q3    1   0.2675  0.8948  0.0894  11.00000  0.05    1.26
Q4    1   0.1644  1.0789  0.1813  11.00000  0.05    1.13
Q5    1   0.4566  0.6905 -0.2935  11.00000  0.05    1.09
Q6    1  -0.3662  1.1415  0.1330  11.00000  0.05    1.09
Q7    1   0.3605  0.8986  0.0313  11.00000  0.05    1.08
Q8    1  -0.2966  1.1006  0.0293  11.00000  0.05    1.07
Q9    1   0.3007  1.1324  0.1113  11.00000  0.05    1.06
Q10   1   0.7499  0.9028  0.1432  11.00000  0.05    1.05
Q11   1   0.2922  0.8559  0.0421  11.00000  0.05    1.05
Q12   1   0.2277  0.8875  0.0995  11.00000  0.05    1.04
Q13   1   0.1665  0.9141  0.0311  11.00000  0.05    1.03
Q14   1   0.2197  0.8996  0.0179  11.00000  0.05    1.02
Q15   1  -0.1908  1.0610  0.0383  11.00000  0.05    0.99
Q16   1  -0.1795  0.9939  0.0874  11.00000  0.05    0.97
Q17   1   0.1348  0.6863  0.1791  11.00000  0.05    0.96
Q18   1   1.2886  0.5826  0.1582  11.00000  0.05    0.95
Q19   1   0.7232  0.8557 -0.0558  11.00000  0.05    0.94
Q20   1   0.7779  0.5193 -0.0159  11.00000  0.05    0.94
;
_shelx_res_checksum              79942

# start Validation Reply Form
_vrf_CHEMW03_CH3NHCH24NH2BiI42.3H2O_RT_Compound2 
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents
;
_vrf_DENSD01_CH3NHCH24NH2BiI42.3H2O_RT_Compound2 
;
PROBLEM: The ratio of the submitted crystal density and that
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents
;
_vrf_PLAT043_CH3NHCH24NH2BiI42.3H2O_RT_Compound2 
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..    1603.26 Check 
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents
;
_vrf_PLAT046_CH3NHCH24NH2BiI42.3H2O_RT_Compound2 
;
PROBLEM: Reported Z, MW and D(calc) are Inconsistent ....      7.706       
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents
;
_vrf_PLAT051_CH3NHCH24NH2BiI42.3H2O_RT_Compound2 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      49.94 %     
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents affecting the absorption coefficient 
;
_vrf_PLAT041_CH3NHCH24NH2BiI42.3H2O_RT_Compound2 
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents
;
_vrf_PLAT068_CH3NHCH24NH2BiI42.3H2O_RT_Compound2 
;
PROBLEM: Reported F000 Differs from Calcd (or Missing)...     Please Check
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents affecting the contributing electron count
;
_vrf_PLAT242_CH3NHCH24NH2BiI42.3H2O_RT_Compound2 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        Bi1 Check 
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher tied with possible disorder in the orientation/ conformation of the 1-Methyldipiperazinium ring. Increased thermal motion due to RT data collection 
;
_vrf_PLAT245_CH3NHCH24NH2BiI42.3H2O_RT_Compound2 
;
PROBLEM: U(iso) H1O2    Smaller than U(eq) O2      by ...      0.025 AngSq 
RESPONSE: Hydrogen positions in the structure have fixed U parameters, not free to refine
;
_vrf_PLAT342_CH3NHCH24NH2BiI42.3H2O_RT_Compound2 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.017 Ang.  
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher tied with possible disorder in the orientation/ conformation of the 1-Methyldipiperazinium ring. Increased thermal motion due to RT data collection 
;
# 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_Compound2_150K
_database_code_depnum_ccdc_archive 'CCDC 1496112'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_date             2016-09-12
_audit_creation_method           'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_chemical_name_systematic        
'1-Methyl-1,4-Dipiperazinium iodobismuthate trihydrate'
_chemical_formula_iupac          '[CH3NH(CH2)4NH2][BiI4]2.3H2O'
_chemical_formula_moiety         'Bi2 I8, (C5 N2 H14), 3(H2O)'
_chemical_formula_sum            'C5 H20 Bi2 I8 N2 O3'
_chemical_formula_weight         1589.4214

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      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                   7.5434(2)
_cell_length_b                   13.0515(5)
_cell_length_c                   13.6716(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.347(3)
_cell_angle_gamma                90
_cell_volume                     1337.76(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    149.95(10)
_cell_measurement_reflns_used    7248
_cell_measurement_theta_min      4.1080
_cell_measurement_theta_max      32.0140
_cell_oxdiff_length_a            7.5441(2)
_cell_oxdiff_length_b            13.0598(5)
_cell_oxdiff_length_c            13.6609(5)
_cell_oxdiff_angle_alpha         89.993(3)
_cell_oxdiff_angle_beta          96.325(3)
_cell_oxdiff_angle_gamma         90.012(3)
_cell_oxdiff_volume              1337.75(8)
_cell_oxdiff_measurement_reflns_used 7248

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    7.890
_exptl_crystal_F_000             2538.000
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.168
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 14 12 0.0844
0 -14 -12 0.1018
10 -3 -3 0.2167
-1 -12 15 0.0665
-10 3 3 0.2014
-10 3 -3 0.1971
0 1 -19 0.1144
2 3 -19 0.1194
4 10 -15 0.1250
-1 12 -14 0.1030
1 12 -15 0.1011
0 18 -2 0.0922
10 3 -4 0.2103
2 18 -3 0.1105
-10 -6 -2 0.2187
0 -16 -9 0.1078
10 4 1 0.2142
1 16 9 0.0877
2 4 18 0.1207
0 -8 -17 0.0984
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
0.2058 13.9457 12.4536 0.1810 -0.9729 -0.1441
-0.0540 -13.9556 -12.4771 -0.1806 0.9707 0.1583
10.4509 -3.3260 -2.9318 0.0430 0.0106 0.9990
-0.5281 -11.9769 14.6119 0.9830 0.1832 -0.0091
-10.4758 2.9079 3.4463 -0.0085 -0.0042 -1.0000
-9.9675 3.0557 -3.0109 -0.2997 0.1466 -0.9288
0.0091 1.0413 -18.9489 -0.8830 0.4456 0.0677
2.0062 3.0238 -18.9415 -0.9210 0.3120 0.2351
4.0081 9.9819 -14.9375 -0.9150 -0.1557 0.3464
-0.9760 12.0024 -13.9488 -0.9659 -0.1701 -0.1319
1.0189 11.9932 -14.9415 -0.9944 -0.1857 0.0554
0.0241 17.9507 -1.9693 -0.5807 -0.7780 -0.1361
9.9781 2.9426 -3.9623 -0.1791 -0.2421 0.9086
2.0190 17.9415 -2.9621 -0.6092 -0.7936 0.0513
-9.9795 -5.9196 -2.0263 -0.0094 0.5357 -0.8607
-0.0169 -15.9311 -8.9991 0.0307 0.9705 0.1639
9.9773 3.9280 1.0260 0.0188 -0.4176 0.8807
1.0142 15.9253 9.0014 -0.0225 -0.9913 -0.0722
1.9922 3.9345 17.9632 0.7183 -0.6917 0.0796
-0.0033 -7.9364 -16.9669 -0.5476 0.8088 0.1318
_exptl_absorpt_coefficient_mu    22.371
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.007
_exptl_absorpt_correction_T_max  0.055
_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 0.747
_oxdiff_exptl_absorpt_empirical_full_max 1.424
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      149.95(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_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            14198
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.3418
_diffrn_reflns_theta_max         32.0964
_diffrn_reflns_theta_full        29.5096
_diffrn_measured_fraction_theta_max 0.8963
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.897
_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      0.0080410000
_diffrn_orient_matrix_UB_12      -0.0274125000
_diffrn_orient_matrix_UB_13      0.0450972000
_diffrn_orient_matrix_UB_21      -0.0209936000
_diffrn_orient_matrix_UB_22      -0.0461741000
_diffrn_orient_matrix_UB_23      -0.0260658000
_diffrn_orient_matrix_UB_31      0.0918855000
_diffrn_orient_matrix_UB_32      -0.0081400000
_diffrn_orient_matrix_UB_33      -0.0039772000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     63.00  89.00   1.00   15.00    --   22.86  77.00 -60.00   26
  2  ω     -4.00  86.00   1.00   15.00    --   22.86  77.00 150.00   90
  3  ω    -31.00  87.00   1.00   15.00    --   22.86   0.00 150.00  118
  4  ω    -18.00  62.00   1.00   15.00    --   22.86 -99.00   0.00   80
  5  ω     23.00  76.00   1.00   15.00    --   22.86-125.00 -68.00   53
  6  ω    -68.00 -26.00   1.00   15.00    --  -22.08 125.00   9.00   42
;
_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             4214
_reflns_number_gt                3779
_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.'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+2.7875P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4214
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_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 0.73423(3) 0.01806(2) 0.40836(2) 0.01259(6) Uani 1 1 d . . . . .
I1 I 0.56052(6) -0.08979(4) 0.23517(3) 0.02821(11) Uani 1 1 d . . . . .
I2 I 1.06168(5) -0.11532(3) 0.39428(3) 0.01816(9) Uani 1 1 d . . . . .
I3 I 0.59528(5) -0.15091(3) 0.56020(3) 0.01771(9) Uani 1 1 d . . . . .
I4 I 0.86271(6) 0.18524(3) 0.29568(3) 0.02419(10) Uani 1 1 d . . . . .
C1 C 0.0812(12) 0.0913(7) -0.0348(6) 0.040(2) Uani 1 1 d . . . . .
C2 C 0.234(3) 0.1276(16) 0.1308(16) 0.060(6) Uani 0.5 1 d . . P . .
C3 C 0.0424(11) -0.0241(6) 0.1041(6) 0.0318(17) Uani 1 1 d . . . . .
N1 N 0.052(2) 0.0820(11) 0.0677(10) 0.040(3) Uani 0.5 1 d . . P . .
N2 N 0.1717(15) 0.0372(9) 0.0471(9) 0.024(2) Uani 0.5 1 d . . P . .
O1 O 0.6623(11) 0.1256(6) 0.0374(5) 0.074(3) Uani 1 1 d . . . . .
H1O1 H 0.6163 0.1649 -0.0093 0.050 Uiso 1 1 d . . . . .
H2O1 H 0.6769 0.1647 0.0892 0.050 Uiso 1 1 d . . . . .
O2 O 0.3573(17) 0.1619(8) 0.1654(8) 0.040(3) Uani 0.5 1 d . . P . .
H1O2 H 0.3754 0.2254 0.1528 0.050 Uiso 0.5 1 d . . P . .
H2O2 H 0.4149 0.1500 0.2218 0.050 Uiso 0.5 1 d . . P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Bi1 0.01573(11) 0.01063(11) 0.01135(11) 0.00060(7) 0.00124(7) 0.00046(7)
I1 0.0295(2) 0.0323(3) 0.0212(2) -0.00998(18) -0.00477(17) -0.00598(18)
I2 0.02132(19) 0.0175(2) 0.0151(2) -0.00725(14) -0.00044(14) 0.00610(14)
I3 0.01845(18) 0.01317(19) 0.0223(2) 0.00656(14) 0.00589(14) 0.00386(14)
I4 0.0320(2) 0.0160(2) 0.0249(2) 0.00870(16) 0.00464(17) -0.00455(16)
C1 0.056(5) 0.043(5) 0.019(4) 0.010(3) -0.002(3) -0.020(4)
C2 0.074(14) 0.045(12) 0.052(13) 0.006(9) -0.034(11) -0.028(10)
C3 0.048(5) 0.022(4) 0.025(4) 0.005(3) 0.000(3) -0.006(3)
N1 0.063(10) 0.031(8) 0.022(7) 0.001(5) -0.005(6) -0.016(7)
N2 0.027(6) 0.020(6) 0.022(6) 0.014(4) -0.004(5) -0.002(5)
O1 0.112(6) 0.072(6) 0.040(4) 0.017(4) 0.014(4) 0.058(5)
O2 0.069(8) 0.018(6) 0.028(6) -0.005(4) -0.015(5) 0.002(5)

_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 I4 2.8989(5) . ?
Bi1 I1 2.9358(5) . ?
Bi1 I2 3.0453(4) . ?
Bi1 I3 3.0993(4) 3_656 ?
Bi1 I2 3.2161(5) 3_756 ?
Bi1 I3 3.2791(4) . ?
I2 Bi1 3.2161(5) 3_756 ?
I3 Bi1 3.0993(4) 3_656 ?
C1 N2 1.432(13) . ?
C1 N1 1.448(16) . ?
C1 C3 1.530(11) 3 ?
C2 O2 1.09(2) . ?
C2 N1 1.65(2) . ?
C2 N2 1.68(2) . ?
C3 N1 1.476(15) . ?
C3 C1 1.530(11) 3 ?
C3 N2 1.538(13) . ?
N1 N2 1.138(19) . ?

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 Bi1 I1 94.469(15) . . ?
I4 Bi1 I2 94.332(14) . . ?
I1 Bi1 I2 88.155(13) . . ?
I4 Bi1 I3 88.453(13) . 3_656 ?
I1 Bi1 I3 94.980(14) . 3_656 ?
I2 Bi1 I3 175.640(13) . 3_656 ?
I4 Bi1 I2 89.520(14) . 3_756 ?
I1 Bi1 I2 174.547(15) . 3_756 ?
I2 Bi1 I2 87.836(11) . 3_756 ?
I3 Bi1 I2 88.835(12) 3_656 3_756 ?
I4 Bi1 I3 172.604(15) . . ?
I1 Bi1 I3 92.449(14) . . ?
I2 Bi1 I3 88.499(12) . . ?
I3 Bi1 I3 88.341(11) 3_656 . ?
I2 Bi1 I3 83.753(12) 3_756 . ?
Bi1 I2 Bi1 92.163(11) . 3_756 ?
Bi1 I3 Bi1 91.660(11) 3_656 . ?
N2 C1 N1 46.5(8) . . ?
N2 C1 C3 114.0(8) . 3 ?
N1 C1 C3 113.8(8) . 3 ?
O2 C2 N1 174(2) . . ?
O2 C2 N2 138(2) . . ?
N1 C2 N2 40.0(8) . . ?
N1 C3 C1 112.2(8) . 3 ?
N1 C3 N2 44.3(7) . . ?
C1 C3 N2 111.2(7) 3 . ?
N2 N1 C1 66.0(10) . . ?
N2 N1 C3 70.7(10) . . ?
C1 N1 C3 115.1(11) . . ?
N2 N1 C2 71.2(13) . . ?
C1 N1 C2 105.6(13) . . ?
C3 N1 C2 103.3(12) . . ?
N1 N2 C1 67.4(10) . . ?
N1 N2 C3 65.0(9) . . ?
C1 N2 C3 112.2(9) . . ?
N1 N2 C2 68.8(13) . . ?
C1 N2 C2 105.1(11) . . ?
C3 N2 C2 99.5(11) . . ?

_refine_diff_density_max         1.841
_refine_diff_density_min         -2.820
_refine_diff_density_rms         0.382

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7

TITL e16mtw021 in P2(1)/c
CELL  0.71073   7.5434  13.0515  13.6716   90.000   96.347   90.000
ZERR     3.00   0.0002   0.0005   0.0005    0.000    0.003    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    N    O    I    BI   H
UNIT  10 4 6 16 4 12
MERG   2
FMAP   2
PLAN   20
ACTA
BOND
L.S.   4
WGHT    0.027500    2.787500
FVAR       1.62545
BI1   5    0.734230    0.018061    0.408357    11.00000    0.01573    0.01063 =
         0.01135    0.00060    0.00124    0.00046
I1    4    0.560520   -0.089785    0.235167    11.00000    0.02955    0.03225 =
         0.02115   -0.00998   -0.00477   -0.00598
I2    4    1.061684   -0.115322    0.394285    11.00000    0.02132    0.01749 =
         0.01511   -0.00725   -0.00044    0.00610
I3    4    0.595281   -0.150909    0.560196    11.00000    0.01845    0.01317 =
         0.02233    0.00656    0.00589    0.00386
I4    4    0.862713    0.185244    0.295676    11.00000    0.03200    0.01603 =
         0.02489    0.00870    0.00464   -0.00455
C1    1    0.081163    0.091299   -0.034845    11.00000    0.05560    0.04255 =
         0.01949    0.01015   -0.00158   -0.01964
C2    1    0.233995    0.127605    0.130830    10.50000    0.07439    0.04537 =
         0.05238    0.00634   -0.03435   -0.02847
C3    1    0.042423   -0.024085    0.104126    11.00000    0.04821    0.02152 =
         0.02466    0.00506   -0.00002   -0.00635
N1    2    0.051908    0.082022    0.067651    10.50000    0.06297    0.03118 =
         0.02237    0.00107   -0.00490   -0.01640
N2    2    0.171716    0.037161    0.047095    10.50000    0.02747    0.02046 =
         0.02200    0.01388   -0.00446   -0.00211
O1    3    0.662256    0.125551    0.037394    11.00000    0.11157    0.07166 =
         0.04044    0.01731    0.01356    0.05756
AFIX   1
H1O1  6    0.616330    0.164940   -0.009260    11.00000    0.05000
H2O1  6    0.676930    0.164670    0.089180    11.00000    0.05000
AFIX   0
O2    3    0.357260    0.161949    0.165373    10.50000    0.06939    0.01819 =
         0.02779   -0.00543   -0.01534    0.00172
AFIX   1
H1O2  6    0.375440    0.225410    0.152830    10.50000    0.05000
H2O2  6    0.414920    0.150010    0.221810    10.50000    0.05000
AFIX   0
HKLF    4

REM  e16mtw021 in P2(1)/c
REM R1 =  0.0323 for    3779 Fo > 4sig(Fo)  and  0.0381 for all    4214 data
REM    109 parameters refined using      0 restraints

END

WGHT      0.0277      2.4140

REM Highest difference peak  1.841,  deepest hole -2.820,  1-sigma level  0.382
Q1    1   0.5611 -0.1369  0.2609  11.00000  0.05    1.84
Q2    1   0.4241  0.3419  0.0843  11.00000  0.05    1.31
Q3    1   0.9122  0.2362  0.3542  11.00000  0.05    1.17
Q4    1   1.1650  0.0179  0.3640  11.00000  0.05    1.16
Q5    1   0.2188 -0.1438  0.1776  11.00000  0.05    1.15
Q6    1   0.6879 -0.0262  0.3547  11.00000  0.05    1.13
Q7    1   0.8457  0.0509  0.3942  11.00000  0.05    1.09
Q8    1   0.6711  0.0774  0.5188  11.00000  0.05    1.08
Q9    1   0.6167  0.0544  0.4290  11.00000  0.05    1.06
Q10   1   0.5599  0.1802  0.2114  11.00000  0.05    1.04
Q11   1   0.7553 -0.1129  0.6549  11.00000  0.05    1.02
Q12   1   0.7758 -0.0876  0.6306  11.00000  0.05    1.01
Q13   1   1.0578  0.0191  0.3202  11.00000  0.05    1.01
Q14   1   0.7619 -0.1200  0.3733  11.00000  0.05    0.99
Q15   1   0.7552  0.0684  0.4721  11.00000  0.05    0.98
Q16   1   0.2453  0.3348  0.1756  11.00000  0.05    0.98
Q17   1   0.6149 -0.0044  0.4283  11.00000  0.05    0.97
Q18   1   0.3339  0.1183  0.0054  11.00000  0.05    0.96
Q19   1   0.4336 -0.0774  0.5166  11.00000  0.05    0.96
Q20   1   0.9359  0.0145  0.4123  11.00000  0.05    0.95
;
_shelx_res_checksum              91954

# start Validation Reply Form
_vrf_ABSMU01_CH3NHCH24NH2BiI42.3H2O_150K_Compound2 
;
PROBLEM: The ratio of given/expected absorption coefficient lies
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents and therefore skews the coefficient value
;
_vrf_CHEMW03_CH3NHCH24NH2BiI42.3H2O_150K_Compound2 
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents
;
_vrf_PLAT043_CH3NHCH24NH2BiI42.3H2O_150K_Compound2 
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..    1603.56 Check 
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents
;
_vrf_PLAT041_CH3NHCH24NH2BiI42.3H2O_150K_Compound2 
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents
;
_vrf_PLAT068_CH3NHCH24NH2BiI42.3H2O_150K_Compound2 
;
PROBLEM: Reported F000 Differs from Calcd (or Missing)...     Please Check
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents affecting the contributing electron count
;
_vrf_PLAT245_CH3NHCH24NH2BiI42.3H2O_150K_Compound2 
;
PROBLEM: U(iso) H1O1    Smaller than U(eq) O1      by ...      0.024 AngSq 
RESPONSE: Hydrogen positions in the structure have fixed U, not free to refine
;
_vrf_PLAT250_CH3NHCH24NH2BiI42.3H2O_150K_Compound2 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.0 Note  
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher tied with possible disorder in the orientation/ conformation of the 1-Methyldipiperazinium ring
;
_vrf_PLAT342_CH3NHCH24NH2BiI42.3H2O_150K_Compound2 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.012 Ang.  
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher tied with possible disorder in the orientation/ conformation of the 1-Methyldipiperazinium ring 
;
# 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_Compound3_RT
_database_code_depnum_ccdc_archive 'CCDC 1496113'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_date             2016-09-13
_audit_creation_method           'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_chemical_name_systematic        
'1,4-Dimethyl-1,4-Dipiperazinium iodobismuthate dihydrate'
_chemical_formula_iupac          '[CH3NH(CH2)4HNCH3][BiI4]2.2H2O'
_chemical_formula_moiety         'Bi I4, 0.5(C6 N2 H16), H2O'
_chemical_formula_sum            'C3 H10 Bi I4 N O'
_chemical_formula_weight         789.68

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'
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      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                   7.7971(3)
_cell_length_b                   13.0868(5)
_cell_length_c                   13.5505(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.925(4)
_cell_angle_gamma                90
_cell_volume                     1369.48(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    286(9)
_cell_measurement_reflns_used    2879
_cell_measurement_theta_min      4.0290
_cell_measurement_theta_max      30.3040
_cell_oxdiff_length_a            7.7983(5)
_cell_oxdiff_length_b            13.0856(7)
_cell_oxdiff_length_c            13.5487(10)
_cell_oxdiff_angle_alpha         89.973(5)
_cell_oxdiff_angle_beta          97.893(6)
_cell_oxdiff_angle_gamma         89.971(5)
_cell_oxdiff_volume              1369.48(16)
_cell_oxdiff_measurement_reflns_used 2879

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    3.830
_exptl_crystal_F_000             2638
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.180
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -12 -14 0.1473
1 -14 12 0.1487
-10 6 -3 0.0817
-7 -15 3 0.1455
10 -6 2 0.1028
-1 14 -12 0.0969
2 -4 -19 0.1121
3 -18 -3 0.1677
5 -12 10 0.1372
-6 -5 -13 0.1084
-10 -6 0 0.0990
-7 12 9 0.0942
5 9 -15 0.1144
-5 12 13 0.1059
-4 3 18 0.1026
3 -3 17 0.1028
2 4 17 0.1010
0 15 10 0.1171
8 9 7 0.0891
8 -9 8 0.1115
9 2 9 0.0969
8 11 -7 0.0799
11 3 -5 0.0855
9 -9 -1 0.1292
8 -8 -12 0.1266
8 -1 -15 0.1026
-10 -6 -4 0.0836
-10 4 9 0.0901
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
2.9648 -12.2188 -13.9374 0.4098 -0.7556 -0.5109
0.9654 -13.8496 12.1494 -0.2197 0.3988 -0.8903
-9.8928 6.4831 -2.5163 0.7187 0.3928 0.5738
-6.5109 -14.8417 2.5051 0.6608 0.3578 -0.6598
10.0260 -5.9363 2.4121 -0.7346 -0.4014 -0.5471
-0.9905 13.9853 -12.0023 0.2148 -0.3911 0.8959
1.9941 -4.0184 -18.9834 0.5036 -0.8851 -0.0032
2.9852 -17.9996 -2.9846 0.1649 -0.3308 -0.9506
4.9913 -11.9872 9.9936 -0.4883 0.1258 -0.8510
-6.0048 -5.0130 -12.9710 0.9388 -0.2619 0.0356
-10.0033 -6.0001 0.0271 0.8551 0.4558 -0.0994
-6.9885 12.0063 8.9940 0.0511 0.7448 0.6483
5.0043 8.9837 -15.0068 -0.0627 -0.8181 0.5516
-4.9882 12.0106 12.9864 -0.2239 0.8125 0.5550
-3.9947 3.0174 17.9895 -0.3049 0.9362 0.0065
2.9995 -2.9819 16.9822 -0.7033 0.5394 -0.4360
2.0051 4.0168 16.9768 -0.7439 0.6125 -0.0548
0.0130 15.0076 9.9755 -0.5585 0.4622 0.6433
8.0068 9.0064 6.9678 -0.9705 -0.0639 0.2056
7.9929 -8.9894 7.9860 -0.7028 -0.0882 -0.7337
9.0015 2.0098 8.9714 -0.9919 -0.0553 -0.2014
8.0065 10.9919 -7.0221 -0.5702 -0.6278 0.4887
11.0001 2.9956 -5.0216 -0.7261 -0.7184 -0.0116
8.9916 -8.9985 -1.0083 -0.4997 -0.5031 -0.6388
7.9910 -8.0100 -11.9977 -0.1001 -0.9005 -0.4248
7.9961 -1.0142 -15.0025 -0.1234 -0.9975 -0.0259
-10.0038 -6.0041 -3.9695 0.9790 0.2926 -0.0479
-9.9943 4.0074 9.0087 0.4105 0.8591 0.2994
_exptl_absorpt_coefficient_mu    21.851
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.008
_exptl_absorpt_correction_T_max  0.047
_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 0.725
_oxdiff_exptl_absorpt_empirical_full_max 1.429
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      286(9)
_diffrn_ambient_environment      air
_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            8720
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.4118
_diffrn_reflns_theta_max         31.9483
_diffrn_measured_fraction_theta_max 0.8887
_diffrn_reflns_theta_full        29.5096
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.888
_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      -0.0756279000
_diffrn_orient_matrix_UB_12      -0.0165701000
_diffrn_orient_matrix_UB_13      -0.0309643000
_diffrn_orient_matrix_UB_21      -0.0476708000
_diffrn_orient_matrix_UB_22      0.0036992000
_diffrn_orient_matrix_UB_23      0.0408334000
_diffrn_orient_matrix_UB_31      -0.0209746000
_diffrn_orient_matrix_UB_32      0.0514771000
_diffrn_orient_matrix_UB_33      -0.0129320000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  44.00   1.00   12.00    --  -22.90  57.00  60.00   84
  2  ω     48.00  73.00   1.00   12.00    --   23.53 178.00 120.00   25
  3  ω    -63.00 -20.00   1.00   12.00    --  -22.90 107.00 176.00   43
  4  ω    -52.00  48.00   1.00   12.00    --  -22.90  19.00-180.00  100
;
_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     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             4206
_reflns_number_gt                3150
_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.'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0269P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4206
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.77130(4) 0.48591(2) 0.09247(2) 0.02781(9) Uani 1 1 d . . . . .
I1 I 0.93799(10) 0.60035(5) 0.26456(5) 0.0597(2) Uani 1 1 d . . . . .
I2 I 0.44658(8) 0.61418(4) 0.10592(4) 0.03944(15) Uani 1 1 d . . . . .
I3 I 1.09274(8) 0.35318(4) 0.06357(4) 0.04047(15) Uani 1 1 d . . . . .
I4 I 0.65299(10) 0.31688(4) 0.20756(5) 0.04716(17) Uani 1 1 d . . . . .
C1 C 0.5452(16) 0.0203(7) 0.1031(7) 0.056(3) Uani 1 1 d . . . . .
H1A H 0.6270 0.0630 0.1450 0.067 Uiso 1 1 calc R U . . .
H1B H 0.4781 -0.0168 0.1466 0.067 Uiso 1 1 calc R U . . .
C2 C 0.4246(18) 0.0885(8) 0.0368(8) 0.072(4) Uani 1 1 d . . . . .
H2A H 0.3282 0.1058 0.0719 0.086 Uiso 1 1 calc R U . . .
H2B H 0.4856 0.1515 0.0269 0.086 Uiso 1 1 calc R U . . .
C3 C 0.745(2) -0.1228(10) 0.1253(10) 0.109(6) Uani 1 1 d . . . . .
H3A H 0.7833 -0.0870 0.1863 0.163 Uiso 1 1 calc R U . . .
H3B H 0.6752 -0.1801 0.1389 0.163 Uiso 1 1 calc R U . . .
H3C H 0.8440 -0.1466 0.0969 0.163 Uiso 1 1 calc R U . . .
N1 N 0.640(2) -0.0518(10) 0.0532(8) 0.155(8) Uani 1 1 d . . . . .
O1 O 0.8303(17) 0.1278(11) 0.9676(8) 0.121(5) Uani 1 1 d . . . . .
H1O1 H 0.74(4) 0.188(17) 0.897(17) 0.300 Uiso 1 1 d . . . . .
H2O1 H 0.68(5) 0.11(2) 0.97(2) 0.310 Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Bi1 0.02823(16) 0.02830(15) 0.02789(15) -0.00063(11) 0.00741(12) -0.00045(12)
I1 0.0567(5) 0.0622(4) 0.0551(4) -0.0246(3) -0.0101(4) -0.0021(4)
I2 0.0379(3) 0.0427(3) 0.0376(3) -0.0144(2) 0.0046(3) 0.0088(3)
I3 0.0373(3) 0.0355(3) 0.0522(4) 0.0142(3) 0.0190(3) 0.0065(3)
I4 0.0596(4) 0.0365(3) 0.0500(4) 0.0114(2) 0.0239(3) -0.0028(3)
C1 0.083(9) 0.046(5) 0.042(5) -0.016(4) 0.020(6) -0.018(6)
C2 0.099(11) 0.067(7) 0.053(7) -0.025(6) 0.021(7) 0.023(7)
C3 0.111(15) 0.092(11) 0.111(12) -0.026(9) -0.026(11) 0.014(10)
N1 0.25(2) 0.127(10) 0.065(7) -0.060(7) -0.059(10) 0.118(13)
O1 0.124(12) 0.164(10) 0.074(6) 0.012(6) 0.013(7) -0.081(9)

_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 2.9213(7) . ?
Bi1 I4 2.9280(6) . ?
Bi1 I2 3.0641(7) . ?
Bi1 I3 3.1181(7) . ?
Bi1 I2 3.2511(6) 3_665 ?
Bi1 I3 3.2629(6) 3_765 ?
I2 Bi1 3.2511(6) 3_665 ?
I3 Bi1 3.2629(6) 3_765 ?
C1 N1 1.427(15) . ?
C1 C2 1.502(15) . ?
C2 N1 1.343(14) 3_655 ?
C3 N1 1.506(16) . ?
N1 C2 1.343(14) 3_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
I1 Bi1 I4 95.76(2) . . ?
I1 Bi1 I2 87.25(2) . . ?
I4 Bi1 I2 93.36(2) . . ?
I1 Bi1 I3 96.26(2) . . ?
I4 Bi1 I3 87.924(18) . . ?
I2 Bi1 I3 176.130(18) . . ?
I1 Bi1 I2 172.25(2) . 3_665 ?
I4 Bi1 I2 88.221(19) . 3_665 ?
I2 Bi1 I2 85.872(16) . 3_665 ?
I3 Bi1 I2 90.522(17) . 3_665 ?
I1 Bi1 I3 92.17(2) . 3_765 ?
I4 Bi1 I3 170.776(19) . 3_765 ?
I2 Bi1 I3 91.716(17) . 3_765 ?
I3 Bi1 I3 86.531(16) . 3_765 ?
I2 Bi1 I3 84.467(17) 3_665 3_765 ?
Bi1 I2 Bi1 94.127(16) . 3_665 ?
Bi1 I3 Bi1 93.469(16) . 3_765 ?
N1 C1 C2 115.6(9) . . ?
N1 C2 C1 117.2(9) 3_655 . ?
C2 N1 C1 120.8(12) 3_655 . ?
C2 N1 C3 118.2(11) 3_655 . ?
C1 N1 C3 111.8(11) . . ?

_refine_diff_density_max         1.923
_refine_diff_density_min         -1.691
_refine_diff_density_rms         0.278

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7


TITL e16mtw037 in P2(1)/c
CELL  0.71073   7.7971  13.0868  13.5505   90.000   97.925   90.000
ZERR     4.00   0.0003   0.0005   0.0006    0.000    0.004    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    N    O    I    BI   H
UNIT  24 8 8 32 8 14
MERG   2
FMAP   2
PLAN   20
ACTA
BOND
L.S.   4
WGHT    0.029300
FVAR       1.60370
BI1   5    0.771301    0.485912    0.092475    11.00000    0.02823    0.02830 =
         0.02789   -0.00063    0.00741   -0.00045
I1    4    0.937993    0.600345    0.264563    11.00000    0.05671    0.06215 =
         0.05515   -0.02460   -0.01009   -0.00210
I2    4    0.446580    0.614179    0.105918    11.00000    0.03789    0.04271 =
         0.03755   -0.01436    0.00465    0.00876
I3    4    1.092737    0.353185    0.063566    11.00000    0.03729    0.03551 =
         0.05221    0.01419    0.01902    0.00649
I4    4    0.652992    0.316880    0.207562    11.00000    0.05964    0.03650 =
         0.04995    0.01143    0.02394   -0.00280
C1    1    0.545179    0.020290    0.103137    11.00000    0.08327    0.04572 =
         0.04195   -0.01601    0.01991   -0.01839
AFIX  23
H1A   6    0.626994    0.062952    0.145019    11.00000   -1.20000
H1B   6    0.478076   -0.016847    0.146550    11.00000   -1.20000
AFIX   0
C2    1    0.424560    0.088492    0.036774    11.00000    0.09873    0.06696 =
         0.05301   -0.02547    0.02087    0.02298
AFIX  23
H2A   6    0.328197    0.105847    0.071876    11.00000   -1.20000
H2B   6    0.485566    0.151466    0.026901    11.00000   -1.20000
AFIX   0
C3    1    0.745211   -0.122807    0.125348    11.00000    0.11077    0.09227 =
         0.11097   -0.02620   -0.02610    0.01447
AFIX  33
H3A   6    0.783335   -0.087015    0.186271    11.00000   -1.50000
H3B   6    0.675152   -0.180082    0.138902    11.00000   -1.50000
H3C   6    0.844040   -0.146581    0.096864    11.00000   -1.50000
AFIX   0
N1    2    0.640275   -0.051814    0.053204    11.00000    0.25050    0.12688 =
         0.06487   -0.05989   -0.05873    0.11818
O1    3    0.830300    0.127824    0.967574    11.00000    0.12387    0.16376 =
         0.07441    0.01156    0.01314   -0.08119
AFIX   2
H1O1  6    0.738632    0.188125    0.897449    11.00000    0.30000
H2O1  6    0.679858    0.105884    0.969105    11.00000    0.31000
AFIX   0
HKLF    4

REM  e16mtw037 in P2(1)/c
REM R1 =  0.0425 for    3150 Fo > 4sig(Fo)  and  0.0654 for all    4206 data
REM     97 parameters refined using      0 restraints

END

WGHT      0.0268      0.0000

REM Highest difference peak  1.923,  deepest hole -1.691,  1-sigma level  0.278
Q1    1   0.8968  0.4872  0.0793  11.00000  0.05    1.92
Q2    1   0.6485  0.4851  0.1040  11.00000  0.05    1.53
Q3    1   0.5739  0.6181  0.0925  11.00000  0.05    1.25
Q4    1   0.6436  0.5620  0.0611  11.00000  0.05    1.17
Q5    1   0.6788  0.5586  0.1175  11.00000  0.05    1.11
Q6    1   0.7427  0.3444  0.2522  11.00000  0.05    1.10
Q7    1   0.5779 -0.1044  0.0629  11.00000  0.05    1.05
Q8    1   1.2278  0.3555  0.0554  11.00000  0.05    1.04
Q9    1   0.6381 -0.0222  0.0509  11.00000  0.05    1.02
Q10   1   0.9625  0.3599  0.0730  11.00000  0.05    1.02
Q11   1   0.8426  0.4808  0.1490  11.00000  0.05    0.99
Q12   1   0.7961  0.4434  0.0514  11.00000  0.05    0.93
Q13   1   0.8654  0.6042  0.1986  11.00000  0.05    0.92
Q14   1   1.0107  0.3397  0.0016  11.00000  0.05    0.92
Q15   1   0.7959  0.6000  0.1406  11.00000  0.05    0.90
Q16   1   0.7207  0.5459  0.1291  11.00000  0.05    0.90
Q17   1   0.7600  0.1425  0.9633  11.00000  0.05    0.88
Q18   1   0.2114  0.0539  0.0312  11.00000  0.05    0.87
Q19   1   0.7680  0.3194  0.1945  11.00000  0.05    0.87
Q20   1   0.7278  0.4230  0.1413  11.00000  0.05    0.86
;
_shelx_res_checksum              67496


# start Validation Reply Form
_vrf_CHEMW01_CH3NHCH24HNCH3BiI42.2H2O_RT_Compound3 
;
PROBLEM: The difference between the given and expected weight for
RESPONSE: Structure moeity formula has been used to represent the unit cell contents
;
_vrf_PLAT305_CH3NHCH24HNCH3BiI42.2H2O_RT_Compound3 
;
PROBLEM: Isolated Hydrogen Atom (Outside Bond Range ??)         H1O1 Check 
RESPONSE: Water molecule hydrogen positions are not accurately positioned and refined but included in the structural model to show the chemical identity of the oxygen positions. Also some thermal motion in the position of the water site. 
;
_vrf_PLAT316_CH3NHCH24HNCH3BiI42.2H2O_RT_Compound3 
;
PROBLEM: Too many H on C in C=N Moiety in Main Residue ..         C2 Check 
RESPONSE: Due to high thermal motion of the dimethyldipiperazinium ring for a RT data collection the dynamic orientation/conformation of the ring is averaged to a position resulting in a short bond length of 1.332A (N1-C2) - incorrectly modelling C=N Moiety. No. of hydrogens correctly modelled
;
_vrf_PLAT355_CH3NHCH24HNCH3BiI42.2H2O_RT_Compound3 
;
PROBLEM: Long    O-H (X0.82,N0.98A)  O1     -   H2O1   ..       1.20 Ang.  
RESPONSE: Water hydrogen positions not accurately modelled in structure and therefore the interatomic H-H distances calculated are likely incorrect 
;
_vrf_PLAT415_CH3NHCH24HNCH3BiI42.2H2O_RT_Compound3 
;
PROBLEM: Short Inter D-H..H-X       H2O1   ..  H2B     ..       1.87 Ang.  
RESPONSE: Water hydrogen positions not accurately modelled in structure and therefore the interatomic H-H distances calculated are likely incorrect 
;
_vrf_PLAT041_CH3NHCH24HNCH3BiI42.2H2O_RT_Compound3 
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: Structure moeity formula has been used to represent the unit cell contents
;
_vrf_PLAT043_CH3NHCH24HNCH3BiI42.2H2O_RT_Compound3 
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..       2.01 Check 
RESPONSE: Structure moeity formula has been used to represent the unit cell contents
;
_vrf_PLAT068_CH3NHCH24HNCH3BiI42.2H2O_RT_Compound3 
;
PROBLEM: Reported F000 Differs from Calcd (or Missing)...     Please Check
RESPONSE: Structure moeity formula has been used to represent the unit cell contents affecting the contributing electron count
;
_vrf_PLAT213_CH3NHCH24HNCH3BiI42.2H2O_RT_Compound3 
;
PROBLEM: Atom N1              has ADP max/min Ratio .....        3.7 prolat
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher tied with increased thermal motion at RT data collection
;
_vrf_PLAT242_CH3NHCH24HNCH3BiI42.2H2O_RT_Compound3 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        Bi1 Check 
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher tied with increased thermal motion at RT data collection
;
_vrf_PLAT342_CH3NHCH24HNCH3BiI42.2H2O_RT_Compound3 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.016 Ang.  
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher tied with increased thermal motion at RT data collection
;
# 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_Compound3_150K
_database_code_depnum_ccdc_archive 'CCDC 1496114'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_date             2016-09-12
_audit_creation_method           'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_chemical_name_systematic        
'1,4-Dimethyl-1,4-Dipiperazinium iodobismuthate dihydrate'
_chemical_formula_iupac          '[CH3NH(CH2)4HNCH3][BiI4]2.2H2O'
_chemical_formula_moiety         'Bi I4, 0.5(C6 N2 H16), H2O'
_chemical_formula_sum            'C3 H10 Bi I4 N O'
_chemical_formula_weight         789.68

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'
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      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                   7.7293(2)
_cell_length_b                   13.0336(3)
_cell_length_c                   13.4990(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.955(3)
_cell_angle_gamma                90
_cell_volume                     1346.79(6)
_cell_formula_units_Z            4.00
_cell_measurement_temperature    150.10(10)
_cell_measurement_reflns_used    4178
_cell_measurement_theta_min      4.0540
_cell_measurement_theta_max      31.4890
_cell_oxdiff_length_a            7.7289(4)
_cell_oxdiff_length_b            13.0317(4)
_cell_oxdiff_length_c            13.5009(7)
_cell_oxdiff_angle_alpha         89.988(3)
_cell_oxdiff_angle_beta          97.938(4)
_cell_oxdiff_angle_gamma         90.021(3)
_cell_oxdiff_volume              1346.79(11)
_cell_oxdiff_measurement_reflns_used 4178

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    3.894
_exptl_crystal_F_000             2704.000
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.181
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -12 13 0.1424
-1 -13 -13 0.1365
11 -1 1 0.1190
1 -17 5 0.1598
-8 11 -4 0.0721
-11 -1 -1 0.0667
-9 -9 2 0.1146
-9 -7 9 0.1115
-9 7 9 0.0665
-8 11 8 0.0728
9 8 -9 0.1146
6 15 -6 0.1189
1 18 -1 0.1274
1 14 12 0.1060
-3 -1 19 0.1268
9 6 6 0.1118
8 -3 10 0.1083
3 -15 10 0.1480
10 -7 3 0.1141
9 -3 -11 0.1120
6 2 -17 0.0952
-4 -11 -12 0.1154
-2 1 -18 0.0828
2 14 -12 0.1054
-9 -7 -7 0.0906
-8 3 -11 0.0722
-5 11 -12 0.0870
-8 1 14 0.0968
-6 11 12 0.0807
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
-4.2758 -12.0412 13.1929 0.1440 -0.4919 -0.8586
-0.5913 -13.4080 -12.7070 -0.2369 0.7917 -0.5631
10.6947 -0.6147 0.9771 0.9204 0.2744 0.2786
1.3081 -17.4851 5.0123 0.4487 0.1311 -0.8840
-8.0128 10.8634 -4.0055 -0.8999 -0.2483 0.3433
-10.9824 -1.1792 -0.9912 -0.9236 -0.2495 -0.3767
-8.9681 -9.1384 2.0149 -0.5821 -0.1814 -0.7439
-8.9774 -7.0854 9.0037 -0.4174 -0.5301 -0.7101
-9.0105 6.9350 8.9847 -0.5845 -0.7841 -0.0102
-8.0206 10.9492 7.9799 -0.5765 -0.7837 0.2298
8.9751 8.0869 -9.0051 0.4054 0.5119 0.7601
5.9605 15.0720 -6.0165 0.1549 0.1658 0.9900
0.9568 18.0346 -1.0238 -0.1592 -0.2537 0.9399
0.9578 14.1218 11.9659 0.2389 -0.7611 0.6170
-3.0061 -0.9121 18.9800 0.2761 -0.9148 -0.3213
8.9700 6.1912 5.9794 0.8335 -0.1211 0.5182
7.9900 -2.8088 9.9874 0.9661 -0.1646 -0.0001
3.0249 -14.9038 10.0065 0.6963 -0.0888 -0.7528
10.0013 -6.8337 3.0002 0.9904 0.2771 -0.0728
9.0023 -2.9435 -10.9877 0.4828 0.8008 0.2290
5.9984 1.9744 -16.9855 0.0136 0.8926 0.4441
-3.9609 -11.1639 -11.9682 -0.5225 0.6215 -0.5587
-1.9880 0.8417 -17.9784 -0.6622 0.7282 0.1591
1.9721 13.9656 -12.0056 -0.3253 0.3381 0.8745
-8.9670 -7.1998 -6.9769 -0.8485 0.1838 -0.5588
-7.9893 2.8016 -10.9862 -0.9930 0.2092 0.0095
-5.0115 10.8527 -11.9975 -0.8677 0.1938 0.5106
-8.0009 0.9775 13.9862 -0.2955 -0.8699 -0.3268
-6.0259 11.0088 11.9739 -0.3035 -0.9054 0.2531

_exptl_absorpt_coefficient_mu    22.220
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.007
_exptl_absorpt_correction_T_max  0.039
_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 0.828
_oxdiff_exptl_absorpt_empirical_full_max 1.349
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.10(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_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            7814
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.2445
_diffrn_reflns_theta_max         31.8571
_diffrn_measured_fraction_theta_max 0.8938
_diffrn_reflns_theta_full        29.5096
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.894
_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      0.0829096000
_diffrn_orient_matrix_UB_12      -0.0116857000
_diffrn_orient_matrix_UB_13      0.0271176000
_diffrn_orient_matrix_UB_21      0.0286856000
_diffrn_orient_matrix_UB_22      -0.0181141000
_diffrn_orient_matrix_UB_23      -0.0445233000
_diffrn_orient_matrix_UB_31      0.0298162000
_diffrn_orient_matrix_UB_32      0.0499782000
_diffrn_orient_matrix_UB_33      -0.0098054000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  84.00   1.00   25.00    --   23.53  57.00-180.00   53
  2  ω     60.00  96.00   1.00   25.00    --   23.53-178.00 -30.00   36
  3  ω    -46.00  93.00   1.00   25.00    --   23.53   0.00 150.00  139
;
_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 99.77
_reflns_odcompleteness_theta     29.51
_reflns_odcompleteness_iscentric 1
_reflns_number_total             4138
_reflns_number_gt                3721
_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.'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)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         4138
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0788
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_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 0.72880(3) 0.51325(2) 0.40736(2) 0.01030(7) Uani 1 1 d . . . . .
I1 I 0.84901(7) 0.68281(3) 0.29176(4) 0.01947(11) Uani 1 1 d . . . . .
I2 I 0.40545(6) 0.64794(3) 0.43554(3) 0.01616(10) Uani 1 1 d . . . . .
I3 I 1.05553(6) 0.38481(3) 0.39404(3) 0.01627(10) Uani 1 1 d . . . . .
I4 I 0.56113(7) 0.39787(4) 0.23463(4) 0.02721(13) Uani 1 1 d . . . . .
C1 C 0.7498(17) 1.1233(8) 0.3767(9) 0.059(4) Uani 1 1 d . . . . .
H1A H 0.6980 1.0881 0.3174 0.088 Uiso 1 1 calc R U . . .
H1B H 0.6599 1.1556 0.4080 0.088 Uiso 1 1 calc R U . . .
H1C H 0.8297 1.1744 0.3591 0.088 Uiso 1 1 calc R U . . .
C2 C 0.9535(12) 0.9784(6) 0.3950(6) 0.0240(17) Uani 1 1 d . . . . .
H2A H 1.0234 1.0194 0.3555 0.029 Uiso 1 1 calc R U . . .
H2B H 0.8764 0.9359 0.3493 0.029 Uiso 1 1 calc R U . . .
C3 C 1.0737(15) 0.9095(7) 0.4642(7) 0.043(3) Uani 1 1 d . . . . .
H3A H 1.0068 0.8506 0.4811 0.051 Uiso 1 1 calc R U . . .
H3B H 1.1644 0.8842 0.4276 0.051 Uiso 1 1 calc R U . . .
N1 N 0.8471(19) 1.0473(9) 0.4482(7) 0.099(5) Uani 1 1 d . . . . .
O1 O 0.6684(13) 0.8734(7) 0.5359(6) 0.080(3) Uani 1 1 d . . . . .
H1O1 H 0.6509 0.8169 0.5024 0.050 Uiso 1 1 d . . . . .
H2O1 H 0.7114 0.9154 0.4963 0.050 Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Bi1 0.00889(12) 0.01018(12) 0.01188(12) -0.00054(8) 0.00160(8) -0.00035(8)
I1 0.0226(2) 0.0144(2) 0.0229(2) 0.00568(17) 0.00849(19) -0.00158(17)
I2 0.0125(2) 0.0140(2) 0.0233(2) 0.00725(16) 0.00681(17) 0.00314(16)
I3 0.0136(2) 0.0180(2) 0.0167(2) -0.00728(16) 0.00040(16) 0.00454(16)
I4 0.0230(3) 0.0280(3) 0.0276(3) -0.0139(2) -0.0071(2) -0.0013(2)
C1 0.067(9) 0.045(6) 0.056(7) -0.013(5) -0.025(6) 0.020(6)
C2 0.033(5) 0.022(4) 0.018(4) -0.010(3) 0.008(3) -0.003(3)
C3 0.059(7) 0.045(5) 0.023(4) -0.018(4) 0.002(4) 0.013(5)
N1 0.148(13) 0.093(8) 0.039(6) -0.037(6) -0.045(7) 0.086(8)
O1 0.107(8) 0.098(6) 0.037(4) -0.015(4) 0.020(5) -0.084(6)

_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 I4 2.9225(5) . ?
Bi1 I1 2.9298(5) . ?
Bi1 I3 3.0559(5) . ?
Bi1 I2 3.1202(5) . ?
Bi1 I3 3.2395(5) 3_766 ?
Bi1 I2 3.2553(5) 3_666 ?
I2 Bi1 3.2553(5) 3_666 ?
I3 Bi1 3.2396(5) 3_766 ?
C1 N1 1.509(13) . ?
C2 N1 1.470(13) . ?
C2 C3 1.518(12) . ?
C3 N1 1.374(12) 3_776 ?
N1 C3 1.374(12) 3_776 ?

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 Bi1 I1 95.826(17) . . ?
I4 Bi1 I3 87.134(15) . . ?
I1 Bi1 I3 93.227(15) . . ?
I4 Bi1 I2 96.463(16) . . ?
I1 Bi1 I2 87.649(14) . . ?
I3 Bi1 I2 176.197(15) . . ?
I4 Bi1 I3 172.687(16) . 3_766 ?
I1 Bi1 I3 88.087(14) . 3_766 ?
I3 Bi1 I3 86.478(13) . 3_766 ?
I2 Bi1 I3 89.854(13) . 3_766 ?
I4 Bi1 I2 92.379(16) . 3_666 ?
I1 Bi1 I2 170.744(15) . 3_666 ?
I3 Bi1 I2 91.450(13) . 3_666 ?
I2 Bi1 I2 87.178(12) . 3_666 ?
I3 Bi1 I2 84.231(13) 3_766 3_666 ?
Bi1 I2 Bi1 92.823(12) . 3_666 ?
Bi1 I3 Bi1 93.522(13) . 3_766 ?
N1 C2 C3 113.4(7) . . ?
N1 C3 C2 116.6(8) 3_776 . ?
C3 N1 C2 117.3(10) 3_776 . ?
C3 N1 C1 113.9(9) 3_776 . ?
C2 N1 C1 110.6(9) . . ?

_refine_diff_density_max         2.886
_refine_diff_density_min         -3.060
_refine_diff_density_rms         0.456

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7

TITL e16mtw033 in P2(1)/c
CELL  0.71073   7.7293  13.0336  13.4990   90.000   97.955   90.000
ZERR     4.00   0.0002   0.0003   0.0004    0.000    0.003    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    N    O    I    BI   H
UNIT  24 8 8 32 8 15
MERG   2
FMAP   2
PLAN   20
ACTA
BOND
L.S.   4
WGHT    0.032400
FVAR       1.54557
BI1   5    0.728795    0.513250    0.407357    11.00000    0.00889    0.01018 =
         0.01188   -0.00054    0.00160   -0.00035
I1    4    0.849008    0.682812    0.291759    11.00000    0.02265    0.01436 =
         0.02291    0.00568    0.00849   -0.00158
I2    4    0.405454    0.647938    0.435542    11.00000    0.01248    0.01395 =
         0.02327    0.00725    0.00681    0.00314
I3    4    1.055531    0.384809    0.394036    11.00000    0.01364    0.01801 =
         0.01669   -0.00728    0.00040    0.00454
I4    4    0.561126    0.397870    0.234630    11.00000    0.02299    0.02798 =
         0.02764   -0.01387   -0.00712   -0.00129
C1    1    0.749841    1.123267    0.376683    11.00000    0.06710    0.04456 =
         0.05557   -0.01308   -0.02542    0.02025
AFIX  33
H1A   6    0.698030    1.088095    0.317431    11.00000   -1.50000
H1B   6    0.659935    1.155650    0.408038    11.00000   -1.50000
H1C   6    0.829665    1.174380    0.359071    11.00000   -1.50000
AFIX   0
C2    1    0.953480    0.978406    0.395023    11.00000    0.03317    0.02197 =
         0.01816   -0.01003    0.00840   -0.00258
AFIX  23
H2A   6    1.023399    1.019377    0.355546    11.00000   -1.20000
H2B   6    0.876387    0.935928    0.349289    11.00000   -1.20000
AFIX   0
C3    1    1.073739    0.909462    0.464226    11.00000    0.05915    0.04517 =
         0.02253   -0.01820    0.00171    0.01323
AFIX  23
H3A   6    1.006758    0.850596    0.481062    11.00000   -1.20000
H3B   6    1.164417    0.884179    0.427555    11.00000   -1.20000
AFIX   0
N1    2    0.847124    1.047310    0.448213    11.00000    0.14796    0.09333 =
         0.03867   -0.03692   -0.04452    0.08622
O1    3    0.668351    0.873420    0.535857    11.00000    0.10661    0.09783 =
         0.03715   -0.01520    0.02037   -0.08442
AFIX   1
H1O1  6    0.650860    0.816880    0.502400    11.00000    0.05000
H2O1  6    0.711370    0.915380    0.496280    11.00000    0.05000
AFIX   0
HKLF    4

REM  e16mtw033 in P2(1)/c
REM R1 =  0.0343 for    3721 Fo > 4sig(Fo)  and  0.0401 for all    4138 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0326      0.0000

REM Highest difference peak  2.886,  deepest hole -3.060,  1-sigma level  0.456
Q1    1   0.9457  1.0871  0.4281  11.00000  0.05    2.21
Q2    1   0.8821  0.5204  0.4095  11.00000  0.05    1.41
Q3    1   1.2818  0.3535  0.4983  11.00000  0.05    1.36
Q4    1   0.8028  0.4305  0.3181  11.00000  0.05    1.25
Q5    1   0.5044  0.6589  0.3255  11.00000  0.05    1.23
Q6    1   0.6693  0.3832  0.4239  11.00000  0.05    1.19
Q7    1   0.5500  0.5429  0.4757  11.00000  0.05    1.19
Q8    1   0.5802  0.5225  0.4062  11.00000  0.05    1.18
Q9    1   0.9834  0.4826  0.3214  11.00000  0.05    1.15
Q10   1   0.8212  0.8214  0.3523  11.00000  0.05    1.15
Q11   1   0.8063  0.3848  0.3567  11.00000  0.05    1.14
Q12   1   0.7576  1.3194  0.3415  11.00000  0.05    1.11
Q13   1   0.5551  0.4377  0.4122  11.00000  0.05    1.10
Q14   1   0.6407  0.5784  0.5234  11.00000  0.05    1.10
Q15   1   1.0982  0.3242  0.5418  11.00000  0.05    1.08
Q16   1   0.5569  0.6611  0.4444  11.00000  0.05    1.08
Q17   1   0.6408  0.5459  0.5301  11.00000  0.05    1.05
Q18   1   0.7010  0.8063  0.6636  11.00000  0.05    1.05
Q19   1   1.2485  0.3930  0.4276  11.00000  0.05    1.04
Q20   1   0.7012  0.8482  0.5990  11.00000  0.05    1.04
;
_shelx_res_checksum              72003

# start Validation Reply Form
_vrf_CHEMW01_CH3NHCH24HNCH3BiI42.2H2O_150K_Compound3 
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PROBLEM: The difference between the given and expected weight for
RESPONSE: Structure moeity formula has been used to represent the unit cell contents
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_vrf_PLAT041_CH3NHCH24HNCH3BiI42.2H2O_150K_Compound3 
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PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: Structure moeity formula has been used to represent the unit cell contents
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_vrf_PLAT043_CH3NHCH24HNCH3BiI42.2H2O_150K_Compound3 
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PROBLEM: Calculated and Reported Mol. Weight Differ by ..       2.01 Check 
RESPONSE: Structure moeity formula has been used to represent the unit cell contents
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_vrf_PLAT068_CH3NHCH24HNCH3BiI42.2H2O_150K_Compound3 
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PROBLEM: Reported F000 Differs from Calcd (or Missing)...     Please Check
RESPONSE: Structure moeity formula based on relative occupancies has been used to represent the unit cell contents affecting the contributing electron count 
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_vrf_PLAT213_CH3NHCH24HNCH3BiI42.2H2O_150K_Compound3 
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PROBLEM: Atom N1              has ADP max/min Ratio .....        3.5 prolat
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher. Additionally, this is tied with disorder in the orientation/ conformation of the dimethyldipiperazinium ring
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_vrf_PLAT234_CH3NHCH24HNCH3BiI42.2H2O_150K_Compound3 
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PROBLEM: Large Hirshfeld Difference N1     --  C2      ..       0.17 Ang.  
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher. Additionally, this is tied with disorder in the orientation/ conformation of the dimethyldipiperazinium ring
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_vrf_PLAT242_CH3NHCH24HNCH3BiI42.2H2O_150K_Compound3 
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PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C2 Check 
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher. Additionally, this is tied with disorder in the orientation/ conformation of the dimethyldipiperazinium ring 
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_vrf_PLAT245_CH3NHCH24HNCH3BiI42.2H2O_150K_Compound3 
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PROBLEM: U(iso) H1O1    Smaller than U(eq) O1      by ...      0.030 AngSq 
RESPONSE: Hydrogen positions have fixed U parameters, not free to refine
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_vrf_PLAT342_CH3NHCH24HNCH3BiI42.2H2O_150K_Compound3 
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PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.013 Ang.  
RESPONSE: Heavy atom hybrid structure - Errors on light atom bond lengths will be higher. Additionally, this is tied with disorder in the orientation/ conformation of the dimethyldipiperazinium ring 
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# end Validation Reply Form

