# 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_1
_audit_block_doi                 10.5517/cc1kbylf
_database_code_depnum_ccdc_archive 'CCDC 1440495'
_audit_update_record             
;
2016-01-22 deposited with the CCDC.
2016-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'I4 Sb, 2(C3 H10 N), I'
_chemical_formula_sum            'C6 H20 I5 N2 Sb'
_chemical_formula_weight         876.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   14.640(12)
_cell_length_b                   16.039(16)
_cell_length_c                   8.430(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1980(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1741
_cell_measurement_theta_min      3.064
_cell_measurement_theta_max      24.987

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.940
_exptl_crystal_F_000             1544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    9.170
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7382
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16452
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.064
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_full        24.987
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1741
_reflns_number_gt                1675
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
#In this lab, the measured crystals were cut from large crystals, and thus, their shapes are usually not so regular. This made it difficult to obtain precise 3D images for face indexing. Therefore, we use multi-scan absorption correction in this lab. As for the large absorption coefficient, it is due to that it contains the Sb atoms. Crystals containing heavy atoms such Sb, Bi, and Pb usually have large absorption coefficient, even for small crystals#
;
 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       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'PRPKAPPA (Ferguson, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²+20.4424P] 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         1733
_refine_ls_number_parameters     68
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0821
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.7968(12) 0.4266(9) 0.6389(16) 0.119(6) Uani 1 1 d D . . . .
H2A H 0.7575 0.4553 0.5640 0.143 Uiso 1 1 calc R U . . .
H2B H 0.8140 0.3735 0.5928 0.143 Uiso 1 1 calc R U . . .
C1 C 0.7480(11) 0.4125(9) 0.7836(19) 0.118(6) Uani 1 1 d D . . . .
H1A H 0.7301 0.4659 0.8278 0.142 Uiso 1 1 calc R U . . .
H1B H 0.7885 0.3858 0.8590 0.142 Uiso 1 1 calc R U . . .
C3 C 0.8828(8) 0.4790(8) 0.668(2) 0.103(5) Uani 1 1 d . . . . .
H3A H 0.8654 0.5339 0.7023 0.154 Uiso 1 1 calc R U . . .
H3B H 0.9176 0.4828 0.5722 0.154 Uiso 1 1 calc R U . . .
H3C H 0.9191 0.4530 0.7494 0.154 Uiso 1 1 calc R U . . .
Sb1 Sb 0.5000 0.33989(4) 0.2500 0.0369(2) Uani 1 2 d S T P . .
I1 I 0.70433(4) 0.33614(4) 0.21853(8) 0.0580(2) Uani 1 1 d . . . . .
I2 I 0.51297(4) 0.22510(4) 0.50636(7) 0.0520(2) Uani 1 1 d . . . . .
I3 I 0.5000 0.5000 0.0000 0.0523(2) Uani 1 2 d S . P . .
N1 N 0.6638(7) 0.3593(5) 0.7634(11) 0.074(3) Uani 1 1 d . . . . .
H1C H 0.6173 0.3911 0.7324 0.112 Uiso 1 1 calc R U . . .
H1D H 0.6501 0.3351 0.8554 0.112 Uiso 1 1 calc R U . . .
H1E H 0.6743 0.3203 0.6906 0.112 Uiso 1 1 calc R U . . .

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
C2 0.175(17) 0.086(10) 0.097(11) 0.005(9) 0.011(11) 0.042(11)
C1 0.133(14) 0.077(9) 0.146(15) -0.006(9) 0.046(12) 0.008(9)
C3 0.058(7) 0.078(9) 0.173(15) 0.025(9) 0.007(9) -0.002(6)
Sb1 0.0477(5) 0.0315(4) 0.0313(4) 0.000 -0.0037(3) 0.000
I1 0.0433(3) 0.0535(4) 0.0773(5) 0.0034(3) -0.0037(3) -0.0002(3)
I2 0.0733(4) 0.0446(3) 0.0381(3) 0.0105(2) -0.0065(3) -0.0003(3)
I3 0.0676(6) 0.0458(5) 0.0436(5) 0.0146(4) 0.0011(4) 0.0089(4)
N1 0.070(6) 0.060(5) 0.093(7) -0.008(5) 0.003(5) -0.005(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
C2 C1 1.432(14) . ?
C2 C3 1.534(19) . ?
C1 N1 1.509(17) . ?
Sb1 I2 2.845(2) . ?
Sb1 I2 2.845(2) 3_655 ?
Sb1 I1 3.004(3) . ?
Sb1 I1 3.004(3) 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
C1 C2 C3 110.9(14) . . ?
C2 C1 N1 113.6(15) . . ?
I2 Sb1 I2 99.36(8) . 3_655 ?
I2 Sb1 I1 89.29(2) . . ?
I2 Sb1 I1 89.22(2) 3_655 . ?
I2 Sb1 I1 89.22(2) . 3_655 ?
I2 Sb1 I1 89.29(2) 3_655 3_655 ?
I1 Sb1 I1 177.70(4) . 3_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C2 C1 N1 -178.4(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1C I3 0.89 3.33 3.849(9) 119.8 1_556
N1 H1C I3 0.89 3.14 3.971(10) 157.1 3_655
N1 H1D I1 0.89 3.16 3.900(10) 141.6 1_556
N1 H1D I2 0.89 3.19 3.885(10) 136.8 3_656
N1 H1E I1 0.89 3.08 3.701(9) 128.3 2_655
N1 H1E I2 0.89 3.21 3.769(9) 122.7 .

_refine_diff_density_max         0.918
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.156

_shelx_res_file                  
;

    1.res created by SHELXL-2014/7

TITL 1 in Pbcn
CELL 0.71073  14.6398  16.0389   8.4298  90.000  90.000  90.000
ZERR   4.00   0.0124   0.0160   0.00765   0.000   0.000   0.000
LATT 1
SYMM 0.5-X, 0.5-Y, 0.5+Z
SYMM -X, Y, 0.5-Z
SYMM 0.5+X, 0.5-Y, -Z
SFAC C  H  N  Sb I
UNIT 24 80 8 4   20
OMIT   0.00  50.00
L.S. 50
ACTA
BOND
conf
htab
eqiv $1 x, y, z+1
htab n1 i3_$1
eqiv $2 -x+1, y, -z+1/2
htab n1 i3_$2
htab n1 i1_$1
eqiv $3 -x+1, y, -z+3/2
htab n1 i2_$3
eqiv $4 -x+3/2, -y+1/2, z+1/2
htab n1 i1_$4
htab n1 i2
DFIX 1.55 0.02 C1 C2
FMAP 2
PLAN 20
WGHT    0.021300   20.442402
FVAR       0.15918
MOLE 1
C2    1    0.796812    0.426596    0.638881    11.00000    0.17456    0.08629 =
         0.09707    0.00465    0.01074    0.04175
AFIX  23
H2A   2    0.757515    0.455262    0.563991    11.00000   -1.20000
H2B   2    0.814037    0.373467    0.592759    11.00000   -1.20000
AFIX   0
C1    1    0.747982    0.412542    0.783572    11.00000    0.13286    0.07685 =
         0.14560   -0.00628    0.04596    0.00806
AFIX  23
H1A   2    0.730136    0.465948    0.827788    11.00000   -1.20000
H1B   2    0.788509    0.385758    0.859004    11.00000   -1.20000
AFIX   0
C3    1    0.882788    0.478970    0.668465    11.00000    0.05843    0.07751 =
         0.17276    0.02527    0.00650   -0.00231
AFIX 137
H3A   2    0.865416    0.533879    0.702288    11.00000   -1.50000
H3B   2    0.917617    0.482774    0.572247    11.00000   -1.50000
H3C   2    0.919150    0.453038    0.749380    11.00000   -1.50000
AFIX   0
SB1   4    0.500000    0.339890    0.250000    10.50000    0.04775    0.03153 =
         0.03134    0.00000   -0.00372    0.00000
I1    5    0.704333    0.336138    0.218527    11.00000    0.04330    0.05355 =
         0.07728    0.00339   -0.00373   -0.00016
I2    5    0.512975    0.225104    0.506364    11.00000    0.07331    0.04456 =
         0.03808    0.01050   -0.00650   -0.00031
I3    5    0.500000    0.500000    0.000000    10.50000    0.06760    0.04577 =
         0.04359    0.01458    0.00114    0.00895
N1    3    0.663791    0.359316    0.763430    11.00000    0.06964    0.06030 =
         0.09338   -0.00777    0.00314   -0.00504
AFIX 137
H1C   2    0.617293    0.391139    0.732448    11.00000   -1.50000
H1D   2    0.650072    0.335091    0.855379    11.00000   -1.50000
H1E   2    0.674349    0.320324    0.690583    11.00000   -1.50000
AFIX   0
HKLF 4

REM  1 in Pbcn
REM R1 =  0.0409 for    1675 Fo > 4sig(Fo)  and  0.0433 for all    1733 data
REM     68 parameters refined using      1 restraints

END

WGHT      0.0199      9.3147

REM Instructions for potential hydrogen bonds
EQIV $5 x, -y+1, z+1/2
HTAB C1 I1_$5
HTAB N1 I3_$1
HTAB N1 I3_$2
HTAB N1 I1_$1
HTAB N1 I2_$3
HTAB N1 I1_$4
HTAB N1 I2

REM Highest difference peak  0.918,  deepest hole -0.635,  1-sigma level  0.156
Q1    1   0.7036  0.3335  0.3267  11.00000  0.05    0.92
Q2    1   0.7236  0.4014  0.6604  11.00000  0.05    0.81
Q3    1   0.8169  0.4309  0.7537  11.00000  0.05    0.63
Q4    1   0.5449  0.2969  0.6225  11.00000  0.05    0.47
Q5    1   0.4698  0.2899  0.6422  11.00000  0.05    0.44
Q6    1   0.7600  0.5112  0.6274  11.00000  0.05    0.44
Q7    1   0.6574  0.5304  0.8751  11.00000  0.05    0.43
Q8    1   0.9186  0.5672  0.8657  11.00000  0.05    0.43
Q9    1   0.5172  0.3458  0.8853  11.00000  0.05    0.43
Q10   1   0.5000  0.3256  0.7500  10.50000  0.05    0.43
Q11   1   0.4629  0.4489  0.1375  11.00000  0.05    0.41
Q12   1   0.7327  0.2685  0.1376  11.00000  0.05    0.40
Q13   1   0.4338  0.3997  0.1564  11.00000  0.05    0.40
Q14   1   0.5119  0.1611  0.6370  11.00000  0.05    0.39
Q15   1   0.9857  0.4178  0.3886  11.00000  0.05    0.39
Q16   1   0.7819  0.2818  0.1652  11.00000  0.05    0.38
Q17   1   0.7390  0.4586  0.8832  11.00000  0.05    0.38
Q18   1   0.7312  0.2598  0.8678  11.00000  0.05    0.37
Q19   1   0.8094  0.4545  0.8556  11.00000  0.05    0.37
Q20   1   0.5584  0.1648  0.3932  11.00000  0.05    0.37
;
_shelx_res_checksum              3671
####################################################################### 
# 
# 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_2
_audit_block_doi                 10.5517/cc1kbymg
_database_code_depnum_ccdc_archive 'CCDC 1440496'
_audit_update_record             
;
2016-01-22 deposited with the CCDC.
2016-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'I4 Sb, 2(C3 H10 N), I'
_chemical_formula_sum            'C6 H20 I5 N2 Sb'
_chemical_formula_weight         876.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   15.645(11)
_cell_length_b                   8.386(5)
_cell_length_c                   29.60(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3884(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    3407
_cell_measurement_theta_min      2.604
_cell_measurement_theta_max      24.999

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.998
_exptl_crystal_F_000             3088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    9.349
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7503
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29348
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.604
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3407
_reflns_number_gt                3066
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          

#In this lab, the measured crystals were cut from large crystals, and thus, their shapes are usually not so regular. This made it difficult to obtain precise 3D images for face indexing. Therefore, we use multi-scan absorption correction in this lab. As for the large absorption coefficient, it is due to that it contains the Sb atoms. Crystals containing heavy atoms such Sb, Bi, and Pb usually have large absorption coefficient, even for small crystals#
;
 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       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'PRPKAPPA (Ferguson, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+335.7228P] 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         3392
_refine_ls_number_parameters     131
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.2025
_refine_ls_wR_factor_gt          0.1959
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.005
_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
C6 C 0.769(2) 0.340(5) 0.1853(9) 0.076(10) Uani 1 1 d . U . . .
H6A H 0.7657 0.4380 0.1686 0.115 Uiso 1 1 calc R U . . .
H6B H 0.7118 0.3045 0.1924 0.115 Uiso 1 1 calc R U . . .
H6C H 0.7970 0.2604 0.1674 0.115 Uiso 1 1 calc R U . . .
C3 C 0.7683(17) 0.250(4) 0.5659(8) 0.058(8) Uani 1 1 d . U . . .
H3A H 0.7142 0.2042 0.5578 0.086 Uiso 1 1 calc R U . . .
H3B H 0.7596 0.3334 0.5877 0.086 Uiso 1 1 calc R U . . .
H3C H 0.8045 0.1693 0.5786 0.086 Uiso 1 1 calc R U . . .
C5 C 0.8188(16) 0.367(3) 0.2293(9) 0.050(6) Uani 1 1 d . U . . .
H5A H 0.8730 0.4179 0.2226 0.060 Uiso 1 1 calc R U . . .
H5B H 0.7866 0.4369 0.2492 0.060 Uiso 1 1 calc R U . . .
C2 C 0.8095(14) 0.317(3) 0.5251(7) 0.033(5) Uani 1 1 d . U . . .
H2A H 0.7681 0.3833 0.5094 0.039 Uiso 1 1 calc R U . . .
H2B H 0.8560 0.3860 0.5346 0.039 Uiso 1 1 calc R U . . .
C1 C 0.8425(16) 0.201(3) 0.4938(8) 0.041(5) Uani 1 1 d . U . . .
H1A H 0.8787 0.1277 0.5104 0.049 Uiso 1 1 calc R U . . .
H1B H 0.7948 0.1405 0.4818 0.049 Uiso 1 1 calc R U . . .
C4 C 0.8340(15) 0.211(3) 0.2522(8) 0.040(5) Uani 1 1 d . U . . .
H4A H 0.8658 0.1401 0.2325 0.048 Uiso 1 1 calc R U . . .
H4B H 0.7801 0.1607 0.2598 0.048 Uiso 1 1 calc R U . . .
N2 N 0.8851(16) 0.246(3) 0.2948(7) 0.061(7) Uani 1 1 d . U . . .
H2C H 0.8626 0.3303 0.3088 0.092 Uiso 1 1 calc R U . . .
H2D H 0.9391 0.2672 0.2874 0.092 Uiso 1 1 calc R U . . .
H2E H 0.8834 0.1620 0.3130 0.092 Uiso 1 1 calc R U . . .
N1 N 0.8917(10) 0.265(2) 0.4557(6) 0.030(4) Uani 1 1 d . U . . .
H1C H 0.8566 0.2842 0.4327 0.045 Uiso 1 1 calc R U . . .
H1D H 0.9309 0.1939 0.4473 0.045 Uiso 1 1 calc R U . . .
H1E H 0.9173 0.3549 0.4640 0.045 Uiso 1 1 calc R U . . .
Sb1 Sb 0.58595(8) 0.25165(15) 0.37503(5) 0.0226(3) Uani 1 1 d . U . . .
I1 I 0.75529(9) 0.49498(16) 0.37353(5) 0.0305(4) Uani 1 1 d . . . . .
I4 I 0.46407(9) 0.00346(16) 0.36953(5) 0.0334(4) Uani 1 1 d . U . . .
I2 I 0.58516(10) 0.2836(2) 0.27423(5) 0.0371(4) Uani 1 1 d . U . . .
I5 I 0.47272(9) 0.51940(16) 0.38046(5) 0.0312(4) Uani 1 1 d . U . . .
I3 I 0.58342(9) 0.22859(18) 0.47585(5) 0.0327(4) Uani 1 1 d . U . . .

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
C6 0.057(19) 0.13(3) 0.045(14) 0.004(15) 0.009(11) 0.022(19)
C3 0.033(15) 0.10(2) 0.037(12) 0.011(13) 0.018(10) -0.001(14)
C5 0.035(13) 0.048(12) 0.067(14) -0.005(10) 0.003(11) 0.003(11)
C2 0.030(11) 0.041(12) 0.027(10) 0.001(8) 0.010(8) 0.000(10)
C1 0.040(13) 0.049(13) 0.034(11) 0.009(9) 0.013(9) 0.017(11)
C4 0.028(12) 0.049(12) 0.045(12) -0.009(9) 0.001(9) -0.019(10)
N2 0.075(17) 0.077(17) 0.032(11) -0.002(10) -0.003(10) -0.022(13)
N1 0.013(8) 0.045(11) 0.032(9) -0.005(8) 0.003(7) -0.002(7)
Sb1 0.0203(7) 0.0200(7) 0.0276(7) -0.0003(5) -0.0003(6) -0.0006(5)
I1 0.0272(7) 0.0263(8) 0.0379(8) 0.0006(6) -0.0021(6) -0.0068(5)
I4 0.0285(7) 0.0251(7) 0.0465(8) -0.0038(6) -0.0007(6) -0.0066(6)
I2 0.0364(9) 0.0510(9) 0.0238(7) -0.0027(6) 0.0015(6) -0.0032(7)
I5 0.0267(7) 0.0241(7) 0.0426(8) -0.0016(6) -0.0035(6) 0.0056(6)
I3 0.0250(7) 0.0469(9) 0.0262(7) 0.0007(6) 0.0005(6) 0.0007(7)

_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
C6 C5 1.54(4) . ?
C3 C2 1.48(3) . ?
C5 C4 1.49(3) . ?
C2 C1 1.44(3) . ?
C1 N1 1.47(3) . ?
C4 N2 1.52(3) . ?
Sb1 I4 2.827(2) . ?
Sb1 I5 2.865(2) . ?
Sb1 I3 2.991(3) . ?
Sb1 I2 2.996(3) . ?

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
C4 C5 C6 110(2) . . ?
C1 C2 C3 115(2) . . ?
N1 C1 C2 116(2) . . ?
C5 C4 N2 107(2) . . ?
I4 Sb1 I5 99.39(8) . . ?
I4 Sb1 I3 90.05(6) . . ?
I5 Sb1 I3 89.23(5) . . ?
I4 Sb1 I2 90.32(6) . . ?
I5 Sb1 I2 89.04(6) . . ?
I3 Sb1 I2 178.26(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2C I1 0.89 2.90 3.73(3) 156.2 .
N2 H2D I2 0.89 2.93 3.75(3) 154.6 6_656
N2 H2E I1 0.89 3.14 3.83(2) 136.1 8_755
N2 H2E I5 0.89 3.24 3.87(2) 130.3 8_755
N1 H1C I1 0.89 2.95 3.767(18) 153.5 .
N1 H1D I5 0.89 2.89 3.701(17) 152.9 8_755
N1 H1E I3 0.89 3.15 3.954(18) 150.8 8_765

_refine_diff_density_max         1.356
_refine_diff_density_min         -1.343
_refine_diff_density_rms         0.312

_shelx_res_file                  
;

    2.res created by SHELXL-2014/7

TITL 2 in Pbca
CELL 0.71073  15.6447   8.3863  29.5984  90.000  90.000  90.000
ZERR   8.00   0.0113   0.0054   0.0236   0.000   0.000   0.000
LATT 1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, 0.5-Z
SYMM 0.5+X, 0.5-Y, -Z
SFAC C  H  N  Sb I
UNIT 48 160 16 8 40
OMIT   0.00  50.00
L.S. 40
ACTA
BOND
htab n2 i1
eqiv $1 x+1/2, y, -z+1/2
htab n2 i2_$1
eqiv $2 -x+3/2, y-1/2, z
htab n2 i1_$2
htab n2 i5_$2
htab n1 i1
htab n1 i5_$2
eqiv $3 -x+3/2, y+1/2, z
htab n1 i3_$3
FMAP 2
PLAN 20
delu
simu
htab
WGHT    0.052400  335.722809
FVAR       0.06405
MOLE 1
C6    1    0.768608    0.339941    0.185304    11.00000    0.05744    0.12746 =
         0.04460    0.00357    0.00917    0.02217
AFIX 137
H6A   2    0.765686    0.437962    0.168623    11.00000   -1.50000
H6B   2    0.711819    0.304475    0.192374    11.00000   -1.50000
H6C   2    0.797012    0.260448    0.167435    11.00000   -1.50000
AFIX   0
C3    1    0.768322    0.250151    0.565892    11.00000    0.03317    0.10306 =
         0.03657    0.01084    0.01847   -0.00078
AFIX 137
H3A   2    0.714239    0.204174    0.557825    11.00000   -1.50000
H3B   2    0.759570    0.333380    0.587674    11.00000   -1.50000
H3C   2    0.804466    0.169327    0.578643    11.00000   -1.50000
AFIX   0
C5    1    0.818757    0.367070    0.229320    11.00000    0.03507    0.04788 =
         0.06694   -0.00537    0.00285    0.00271
AFIX  23
H5A   2    0.872995    0.417859    0.222610    11.00000   -1.20000
H5B   2    0.786605    0.436886    0.249167    11.00000   -1.20000
AFIX   0
C2    1    0.809459    0.317299    0.525103    11.00000    0.02999    0.04066 =
         0.02718    0.00052    0.01032    0.00033
AFIX  23
H2A   2    0.768074    0.383287    0.509421    11.00000   -1.20000
H2B   2    0.856039    0.385956    0.534559    11.00000   -1.20000
AFIX   0
C1    1    0.842500    0.201207    0.493790    11.00000    0.03959    0.04861 =
         0.03449    0.00932    0.01317    0.01676
AFIX  23
H1A   2    0.878679    0.127677    0.510352    11.00000   -1.20000
H1B   2    0.794837    0.140457    0.481830    11.00000   -1.20000
AFIX   0
C4    1    0.834025    0.211048    0.252171    11.00000    0.02799    0.04863 =
         0.04454   -0.00895    0.00055   -0.01873
AFIX  23
H4A   2    0.865807    0.140074    0.232488    11.00000   -1.20000
H4B   2    0.780101    0.160723    0.259806    11.00000   -1.20000
AFIX   0
N2    3    0.885086    0.246306    0.294786    11.00000    0.07500    0.07718 =
         0.03189   -0.00218   -0.00250   -0.02223
AFIX 137
H2C   2    0.862616    0.330272    0.308826    11.00000   -1.50000
H2D   2    0.939084    0.267238    0.287415    11.00000   -1.50000
H2E   2    0.883414    0.162025    0.313038    11.00000   -1.50000
AFIX   0
N1    3    0.891655    0.264816    0.455708    11.00000    0.01291    0.04515 =
         0.03152   -0.00541    0.00264   -0.00164
AFIX 137
H1C   2    0.856641    0.284222    0.432656    11.00000   -1.50000
H1D   2    0.930914    0.193929    0.447332    11.00000   -1.50000
H1E   2    0.917271    0.354939    0.464003    11.00000   -1.50000
AFIX   0
SB1   4    0.585953    0.251652    0.375033    11.00000    0.02028    0.02001 =
         0.02757   -0.00032   -0.00027   -0.00061
I1    5    0.755286    0.494980    0.373528    11.00000    0.02720    0.02630 =
         0.03789    0.00064   -0.00209   -0.00684
I4    5    0.464073    0.003461    0.369529    11.00000    0.02850    0.02513 =
         0.04653   -0.00375   -0.00069   -0.00659
I2    5    0.585160    0.283596    0.274228    11.00000    0.03645    0.05098 =
         0.02382   -0.00270    0.00152   -0.00324
I5    5    0.472718    0.519402    0.380457    11.00000    0.02673    0.02411 =
         0.04262   -0.00161   -0.00346    0.00560
I3    5    0.583421    0.228592    0.475851    11.00000    0.02503    0.04689 =
         0.02623    0.00067    0.00050    0.00068
HKLF 4

REM  2 in Pbca
REM R1 =  0.0890 for    3066 Fo > 4sig(Fo)  and  0.0997 for all    3392 data
REM    131 parameters refined using     56 restraints

END

WGHT      0.0524    105.6762

REM Instructions for potential hydrogen bonds
HTAB C2 I3
HTAB C4 I2_$2
HTAB C4 I2
HTAB N2 I1
HTAB N2 I2_$1
HTAB N2 I1_$2
HTAB N2 I5_$2
HTAB N1 I1
HTAB N1 I5_$2
HTAB N1 I3_$3

REM Highest difference peak  1.356,  deepest hole -1.343,  1-sigma level  0.312
Q1    1   0.7420  0.5158  0.3914  11.00000  0.05    1.36
Q2    1   0.7477  0.2239  0.1829  11.00000  0.05    1.17
Q3    1   0.5947  0.1831  0.2744  11.00000  0.05    1.16
Q4    1   0.7960  0.0013  0.2686  11.00000  0.05    0.98
Q5    1   0.5857  0.3273  0.4734  11.00000  0.05    0.97
Q6    1   0.8082  0.1916  0.5208  11.00000  0.05    0.95
Q7    1   0.7816  0.5302  0.3291  11.00000  0.05    0.94
Q8    1   0.7655  0.4271  0.3799  11.00000  0.05    0.93
Q9    1   0.7792  0.0176  0.3028  11.00000  0.05    0.92
Q10   1   0.7606  0.1268  0.5255  11.00000  0.05    0.92
Q11   1   0.8556  0.0715  0.1600  11.00000  0.05    0.91
Q12   1   0.6265  0.2152  0.4697  11.00000  0.05    0.89
Q13   1   0.7646  0.2443  0.2241  11.00000  0.05    0.88
Q14   1   0.6961  0.3292  0.3241  11.00000  0.05    0.86
Q15   1   0.7784  0.3074  0.2813  11.00000  0.05    0.86
Q16   1   0.7225  0.4995  0.2320  11.00000  0.05    0.85
Q17   1   0.7807  0.1490  0.5713  11.00000  0.05    0.85
Q18   1   0.7597  0.2784  0.5912  11.00000  0.05    0.85
Q19   1   0.6616  0.4177  0.4312  11.00000  0.05    0.85
Q20   1   0.7074  0.4164  0.4569  11.00000  0.05    0.84
;
_shelx_res_checksum              30205
# start Validation Reply Form
_vrf_PLAT342_2                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.035 Ang.  
RESPONSE:The weaker diffraction points were collectted at low temperture
;
# end Validation Reply Form
