# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_X_ma
_database_code_depnum_ccdc_archive 'CCDC 1034600'
_audit_update_record             
;
2014-12-11 deposited with the CCDC.
2015-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        '[(N-methylbenzothiazole-2-thione)ICl] '
_chemical_name_common            '[(mbtt)ICl] '
_chemical_melting_point          407-409
_chemical_formula_moiety         'C8 H7 Cl I N S2'
_chemical_formula_sum            'C8 H7 Cl I N S2'
_chemical_formula_weight         343.62

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   9.0044(11)
_cell_length_b                   6.6957(8)
_cell_length_c                   17.835(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1075.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8578
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      33.12

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.123
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.063
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    3.567
_shelx_estimated_absorpt_T_min   0.617
_shelx_estimated_absorpt_T_max   0.717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6798
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  'flat graphite crystal'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_device       
'62mm x 62mm CCD camera on three-circle goniostat'
_diffrn_detector_area_resol_mean 16 # 8 for binned mode
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_reflns_number            13611
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.284
_diffrn_reflns_theta_max         33.175
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2209
_reflns_number_gt                2033
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'CrystaMaker (CrystalMaker Software ltd., 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2008)'

_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)+(0.0177P)²+0.3639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2209
_refine_ls_number_parameters     84
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0163
_refine_ls_wR_factor_ref         0.0372
_refine_ls_wR_factor_gt          0.0364
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.010
_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
I1 I 0.82923(2) 0.2500 1.21141(2) 0.01574(3) Uani 1 2 d S T P . .
Cl1 Cl 0.74658(5) 0.2500 1.35214(3) 0.02318(9) Uani 1 2 d S T P . .
S2 S 0.56998(5) 0.2500 1.06839(2) 0.01410(7) Uani 1 2 d S T P . .
S1 S 0.90906(5) 0.2500 1.07432(2) 0.01843(8) Uani 1 2 d S T P . .
N1 N 0.73658(17) 0.2500 0.95209(8) 0.0151(3) Uani 1 2 d S T P . .
C4 C 0.2959(2) 0.2500 0.88702(10) 0.0189(3) Uani 1 2 d S T P . .
H4 H 0.1938 0.2500 0.8736 0.023 Uiso 1 2 calc R U P . .
C3 C 0.3349(2) 0.2500 0.96220(10) 0.0165(3) Uani 1 2 d S T P . .
H3 H 0.2613 0.2500 1.0003 0.020 Uiso 1 2 calc R U P . .
C2 C 0.4854(2) 0.2500 0.98002(9) 0.0139(3) Uani 1 2 d S T P . .
C1 C 0.7429(2) 0.2500 1.02731(9) 0.0147(3) Uani 1 2 d S T P . .
C5 C 0.4032(2) 0.2500 0.83072(10) 0.0219(3) Uani 1 2 d S T P . .
H5 H 0.3729 0.2500 0.7797 0.026 Uiso 1 2 calc R U P . .
C6 C 0.5529(2) 0.2500 0.84782(10) 0.0196(3) Uani 1 2 d S T P . .
H6 H 0.6261 0.2500 0.8095 0.023 Uiso 1 2 calc R U P . .
C7 C 0.5923(2) 0.2500 0.92338(9) 0.0151(3) Uani 1 2 d S T P . .
C8 C 0.8685(2) 0.2500 0.90335(11) 0.0216(3) Uani 1 2 d DS T P . .
H8A H 0.867(2) 0.3679(18) 0.8724(9) 0.032 Uiso 1 1 d D U . . .
H8B H 0.951(2) 0.2500 0.9355(12) 0.032 Uiso 1 2 d DS U 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
I1 0.01310(6) 0.01828(5) 0.01585(5) 0.000 -0.00212(4) 0.000
Cl1 0.0158(2) 0.0362(2) 0.01747(18) 0.000 0.00061(15) 0.000
S2 0.01191(19) 0.01644(15) 0.01396(16) 0.000 -0.00043(14) 0.000
S1 0.0118(2) 0.02683(19) 0.01661(18) 0.000 -0.00188(16) 0.000
N1 0.0106(7) 0.0196(6) 0.0149(6) 0.000 -0.0002(5) 0.000
C4 0.0146(8) 0.0219(7) 0.0202(8) 0.000 -0.0043(6) 0.000
C3 0.0134(8) 0.0168(6) 0.0192(7) 0.000 -0.0012(6) 0.000
C2 0.0132(8) 0.0127(5) 0.0159(6) 0.000 -0.0009(6) 0.000
C1 0.0111(8) 0.0159(6) 0.0172(7) 0.000 -0.0006(6) 0.000
C5 0.0206(9) 0.0290(8) 0.0161(7) 0.000 -0.0035(7) 0.000
C6 0.0179(9) 0.0263(7) 0.0145(7) 0.000 0.0008(6) 0.000
C7 0.0124(8) 0.0160(6) 0.0171(7) 0.000 -0.0008(6) 0.000
C8 0.0114(8) 0.0334(9) 0.0199(8) 0.000 0.0037(6) 0.000

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 S1 2.5483(5) . ?
I1 Cl1 2.6180(6) . ?
S2 C1 1.7209(18) . ?
S2 C2 1.7507(17) . ?
S1 C1 1.7151(18) . ?
N1 C1 1.343(2) . ?
N1 C7 1.397(2) . ?
N1 C8 1.472(2) . ?
C4 C3 1.386(3) . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C3 C2 1.392(2) . ?
C3 H3 0.9500 . ?
C2 C7 1.395(2) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(2) . ?
C6 H6 0.9500 . ?
C8 H8A 0.963(12) . ?
C8 H8B 0.937(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 I1 Cl1 179.868(15) . . ?
C1 S2 C2 90.59(8) . . ?
C1 S1 I1 102.89(6) . . ?
C1 N1 C7 113.94(15) . . ?
C1 N1 C8 123.78(16) . . ?
C7 N1 C8 122.28(15) . . ?
C3 C4 C5 121.45(18) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C3 C2 117.87(17) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C2 C7 120.42(15) . . ?
C3 C2 S2 129.00(13) . . ?
C7 C2 S2 110.58(13) . . ?
N1 C1 S1 121.70(14) . . ?
N1 C1 S2 112.77(13) . . ?
S1 C1 S2 125.53(10) . . ?
C6 C5 C4 121.13(17) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 117.51(17) . . ?
C5 C6 H6 121.2 . . ?
C7 C6 H6 121.2 . . ?
C6 C7 C2 121.62(17) . . ?
C6 C7 N1 126.27(17) . . ?
C2 C7 N1 112.11(15) . . ?
N1 C8 H8A 109.0(11) . . ?
N1 C8 H8B 106.0(15) . . ?
H8A C8 H8B 111.2(13) . . ?

_refine_diff_density_max         0.593
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.157

_shelxl_version_number           2014-3

_shelx_res_file                  
;
TITL X_ma in Pnma
CELL 0.71073 9.0044 6.6957 17.835 90 90 90
ZERR 4 0.0011 0.0008 0.0021 0 0 0
LATT 1
SYMM 0.5+X,0.5-Y,0.5-Z
SYMM -X,0.5+Y,-Z
SYMM 0.5-X,-Y,0.5+Z
SFAC C H N S Cl I
UNIT 32 28 4 8 4 4
LIST 4
EQIV $1 +X,0.5-Y,+Z
DFIX 0.97 C8 H8b
DFIX 0.97 C8 H8a
DANG 1.584003 H8b H8a
DANG 1.584003 H8a H8a_$1
L.S. 4
PLAN  -14 0 0
SIZE 0.1 0.1 0.15
TEMP -153.15
ACTA
FMAP 2
BOND $H

WGHT    0.017700    0.363900
FVAR       0.06941
I1    6    0.829234    0.250000    1.211406    10.50000    0.01310    0.01828 =
         0.01585    0.00000   -0.00212    0.00000
CL1   5    0.746581    0.250000    1.352141    10.50000    0.01582    0.03625 =
         0.01747    0.00000    0.00061    0.00000
S2    4    0.569976    0.250000    1.068395    10.50000    0.01191    0.01644 =
         0.01396    0.00000   -0.00043    0.00000
S1    4    0.909061    0.250000    1.074324    10.50000    0.01185    0.02683 =
         0.01661    0.00000   -0.00188    0.00000
N1    3    0.736581    0.250000    0.952094    10.50000    0.01063    0.01962 =
         0.01494    0.00000   -0.00022    0.00000
C4    1    0.295928    0.250000    0.887021    10.50000    0.01457    0.02187 =
         0.02025    0.00000   -0.00435    0.00000
AFIX  43
H4    2    0.193834    0.250000    0.873589    10.50000   -1.20000
AFIX   0
C3    1    0.334906    0.250000    0.962196    10.50000    0.01340    0.01677 =
         0.01919    0.00000   -0.00120    0.00000
AFIX  43
H3    2    0.261265    0.250000    1.000340    10.50000   -1.20000
AFIX   0
C2    1    0.485364    0.250000    0.980016    10.50000    0.01318    0.01267 =
         0.01592    0.00000   -0.00090    0.00000
C1    1    0.742904    0.250000    1.027307    10.50000    0.01113    0.01587 =
         0.01723    0.00000   -0.00063    0.00000
C5    1    0.403173    0.250000    0.830719    10.50000    0.02059    0.02904 =
         0.01609    0.00000   -0.00354    0.00000
AFIX  43
H5    2    0.372885    0.250000    0.779695    10.50000   -1.20000
AFIX   0
C6    1    0.552858    0.250000    0.847822    10.50000    0.01788    0.02630 =
         0.01451    0.00000    0.00085    0.00000
AFIX  43
H6    2    0.626145    0.250000    0.809504    10.50000   -1.20000
AFIX   0
C7    1    0.592274    0.250000    0.923380    10.50000    0.01237    0.01599 =
         0.01707    0.00000   -0.00079    0.00000
C8    1    0.868462    0.250000    0.903349    10.50000    0.01144    0.03343 =
         0.01993    0.00000    0.00368    0.00000
H8A   2    0.866884    0.367937    0.872423    11.00000   -1.50000
H8B   2    0.950729    0.250000    0.935514    10.50000   -1.50000
HKLF 4

REM  X_ma in Pnma
REM R1 =  0.0163 for    2033 Fo > 4sig(Fo)  and  0.0195 for all    2209 data
REM     84 parameters refined using      4 restraints

END

WGHT      0.0177      0.3639

REM Highest difference peak  0.593,  deepest hole -0.980,  1-sigma level  0.157
Q1    1   0.8184  0.3699  1.2110  11.00000  0.05    0.59
Q2    1   0.3265  0.2500  0.9225  10.50000  0.05    0.42
Q3    1   0.5383  0.4453  1.1951  11.00000  0.05    0.39
Q4    1   0.7437  0.2500  0.9876  10.50000  0.05    0.39
Q5    1   0.6583  0.4544  1.2041  11.00000  0.05    0.38
Q6    1   0.3595  0.2500  0.8597  10.50000  0.05    0.36
Q7    1   0.9172  0.4503  1.1268  11.00000  0.05    0.36
Q8    1   0.9436  0.4217  1.2140  11.00000  0.05    0.36
Q9    1   0.7053  0.4548  1.3282  11.00000  0.05    0.36
Q10   1   0.5352  0.2500  0.9493  10.50000  0.05    0.36
Q11   1   0.6305  0.4342  1.3018  11.00000  0.05    0.35
Q12   1   0.4852  0.2500  0.8348  10.50000  0.05    0.35
Q13   1   0.5628  0.4357  1.2804  11.00000  0.05    0.35
Q14   1   0.5799  0.2500  0.8820  10.50000  0.05    0.34
;
_shelx_res_checksum              77432

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_mbtt_IBr
_database_code_depnum_ccdc_archive 'CCDC 1034601'
_audit_update_record             
;
2014-11-17 deposited with the CCDC.
2015-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        '[(N-methylbenzothiazole-2-thione)IBr] '
_chemical_name_common            '[(mbtt)IBr] '
_chemical_melting_point          416-417
_chemical_formula_moiety         'C8 H7 Br I N S2'
_chemical_formula_sum            'C8 H7 Br I N S2'
_chemical_formula_weight         388.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   12.4376(2)
_cell_length_b                   21.0096(4)
_cell_length_c                   4.22389(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1103.74(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6588
_cell_measurement_theta_min      4.1060
_cell_measurement_theta_max      76.5640

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.335
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.023
_exptl_absorpt_coefficient_mu    30.202
_shelx_estimated_absorpt_T_min   0.032
_shelx_estimated_absorpt_T_max   0.542
_exptl_absorpt_correction_T_min  0.30076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   micro-source
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_reflns_number            11418
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         4.131
_diffrn_reflns_theta_max         76.979
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_point_group_measured_fraction_full 0.850
_reflns_number_total             1965
_reflns_number_gt                1890
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.472
_reflns_Friedel_fraction_max     0.624
_reflns_Friedel_fraction_full    0.648

_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, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'CrystaMaker (CrystalMaker Software ltd., 2012)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0384P)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_abs_structure_details 
;
 Flack x determined using 574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1965
_refine_ls_number_parameters     119
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.26972(3) 0.86618(2) -0.03320(15) 0.02033(13) Uani 1 1 d . . . . .
Br1 Br 0.39444(6) 0.96167(3) -0.1989(2) 0.02616(18) Uani 1 1 d . . . . .
S1 S 0.13948(14) 0.76801(8) 0.1247(5) 0.0248(4) Uani 1 1 d . . . . .
S2 S 0.36244(13) 0.72512(7) 0.3237(5) 0.0219(3) Uani 1 1 d . . . . .
N1 N 0.1919(5) 0.6634(2) 0.454(2) 0.0224(12) Uani 1 1 d . . . . .
C1 C 0.2237(5) 0.7164(3) 0.304(2) 0.0203(14) Uani 1 1 d . . . . .
C2 C 0.3749(6) 0.6543(3) 0.5413(17) 0.0205(16) Uani 1 1 d . . . . .
C3 C 0.4683(6) 0.6263(3) 0.653(2) 0.0247(15) Uani 1 1 d . . . . .
H3 H 0.5369 0.6443 0.6126 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4569(6) 0.5708(4) 0.826(2) 0.0264(15) Uani 1 1 d . . . . .
H4 H 0.5192 0.5504 0.9080 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3557(7) 0.5440(4) 0.883(2) 0.0285(18) Uani 1 1 d . . . . .
H5 H 0.3506 0.5058 1.0023 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2630(6) 0.5721(4) 0.770(2) 0.0263(16) Uani 1 1 d . . . . .
H6 H 0.1941 0.5543 0.8108 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2745(6) 0.6274(3) 0.595(2) 0.0224(16) Uani 1 1 d . . . . .
C8 C 0.0784(6) 0.6440(3) 0.465(3) 0.0309(16) Uani 1 1 d . . . . .
H8A H 0.0725 0.6023 0.5679 0.046 Uiso 1 1 calc R U . . .
H8B H 0.0500 0.6412 0.2490 0.046 Uiso 1 1 calc R U . . .
H8C H 0.0370 0.6754 0.5854 0.046 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
I1 0.0211(2) 0.02205(18) 0.0178(2) -0.0002(2) -0.0005(2) 0.00160(12)
Br1 0.0272(3) 0.0214(3) 0.0299(4) 0.0013(3) 0.0054(3) 0.0005(3)
S1 0.0201(8) 0.0261(7) 0.0282(10) 0.0019(8) -0.0017(8) -0.0005(6)
S2 0.0184(7) 0.0223(6) 0.0249(9) 0.0008(7) 0.0000(8) -0.0028(5)
N1 0.023(3) 0.020(2) 0.024(3) -0.004(3) -0.001(3) -0.002(2)
C1 0.019(3) 0.024(3) 0.017(4) -0.001(3) 0.001(3) -0.001(2)
C2 0.030(4) 0.020(3) 0.011(4) -0.001(2) 0.003(3) -0.001(2)
C3 0.026(4) 0.025(3) 0.023(4) -0.002(3) 0.000(3) 0.000(3)
C4 0.030(4) 0.030(3) 0.019(4) 0.002(3) 0.000(4) 0.002(3)
C5 0.036(4) 0.025(3) 0.024(5) 0.001(3) -0.003(3) 0.001(3)
C6 0.031(4) 0.022(3) 0.026(5) 0.001(3) 0.002(3) -0.006(3)
C7 0.023(4) 0.021(3) 0.023(4) -0.006(3) -0.002(3) 0.000(2)
C8 0.026(3) 0.025(3) 0.042(5) 0.003(5) 0.009(5) -0.003(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
I1 Br1 2.6308(8) . yes
I1 S1 2.7060(18) . yes
S1 C1 1.687(8) . yes
S2 C1 1.738(6) . yes
S2 C2 1.756(7) . yes
N1 C1 1.341(10) . yes
N1 C7 1.407(10) . yes
N1 C8 1.470(9) . yes
C2 C3 1.385(11) . ?
C2 C7 1.388(10) . ?
C3 C4 1.384(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(12) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
Br1 I1 S1 178.76(6) . . ?
C1 S1 I1 103.2(2) . . ?
C1 S2 C2 91.3(4) . . ?
C1 N1 C7 115.4(6) . . ?
C1 N1 C8 121.9(7) . . ?
C7 N1 C8 122.7(7) . . ?
N1 C1 S1 124.3(5) . . ?
N1 C1 S2 111.0(5) . . ?
S1 C1 S2 124.8(4) . . ?
C3 C2 C7 121.7(7) . . ?
C3 C2 S2 127.8(6) . . ?
C7 C2 S2 110.5(6) . . ?
C4 C3 C2 116.9(7) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 121.4(8) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 121.3(7) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 117.2(7) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 H6 121.4 . . ?
C6 C7 C2 121.4(7) . . ?
C6 C7 N1 126.8(7) . . ?
C2 C7 N1 111.7(7) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
C7 N1 C1 S1 -178.7(6) . . . . ?
C8 N1 C1 S1 2.4(13) . . . . ?
C7 N1 C1 S2 0.7(10) . . . . ?
C8 N1 C1 S2 -178.2(8) . . . . ?
I1 S1 C1 N1 172.2(7) . . . . ?
I1 S1 C1 S2 -7.1(6) . . . . ?
C2 S2 C1 N1 0.1(7) . . . . ?
C2 S2 C1 S1 179.5(6) . . . . ?
C1 S2 C2 C3 179.4(8) . . . . ?
C1 S2 C2 C7 -0.9(6) . . . . ?
C7 C2 C3 C4 -1.2(13) . . . . ?
S2 C2 C3 C4 178.5(7) . . . . ?
C2 C3 C4 C5 0.5(14) . . . . ?
C3 C4 C5 C6 -0.3(14) . . . . ?
C4 C5 C6 C7 0.7(13) . . . . ?
C5 C6 C7 C2 -1.4(13) . . . . ?
C5 C6 C7 N1 179.2(8) . . . . ?
C3 C2 C7 C6 1.7(13) . . . . ?
S2 C2 C7 C6 -178.0(7) . . . . ?
C3 C2 C7 N1 -178.8(7) . . . . ?
S2 C2 C7 N1 1.4(9) . . . . ?
C1 N1 C7 C6 178.0(9) . . . . ?
C8 N1 C7 C6 -3.1(15) . . . . ?
C1 N1 C7 C2 -1.4(11) . . . . ?
C8 N1 C7 C2 177.5(9) . . . . ?

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
C6 H6 Br1 0.95 3.05 3.775(8) 134.5 3_546
C8 H8A Br1 0.98 2.77 3.489(8) 130.6 4_466

_refine_diff_density_max         1.224
_refine_diff_density_min         -1.013
_refine_diff_density_rms         0.151

_shelxl_version_number           2014-3

_shelx_res_file                  
;
TITL exp_3321 in Pna21 #33 (CF, yellow needle)
CELL 1.54184 12.437624 21.009574 4.223895 90 90 90
ZERR 4 0.000246 0.000379 0.000078 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SFAC C H Br I N S
UNIT 32 28 4 4 4 8
EQIV $1 0.5-X,-0.5+Y,1.5+Z
EQIV $2 -0.5+X,1.5-Y,1+Z
L.S. 8
PLAN  -10
SIZE 0.0231 0.0238 0.3621
TEMP -153
HTAB C6 Br1_$1
HTAB C8 Br1_$2
LIST 4
BOND $H
HTAB 2.0
MORE -1
CONF
fmap 2
acta

WGHT    0.038400
FVAR       3.04132
I1    4    0.269722    0.866178   -0.033197    11.00000    0.02115    0.02205 =
         0.01779   -0.00017   -0.00047    0.00160
BR1   3    0.394436    0.961668   -0.198924    11.00000    0.02721    0.02140 =
         0.02986    0.00127    0.00541    0.00050
S1    6    0.139480    0.768013    0.124724    11.00000    0.02006    0.02614 =
         0.02819    0.00188   -0.00169   -0.00054
S2    6    0.362444    0.725120    0.323685    11.00000    0.01839    0.02229 =
         0.02494    0.00080    0.00005   -0.00278
N1    5    0.191851    0.663400    0.454442    11.00000    0.02287    0.01978 =
         0.02447   -0.00369   -0.00076   -0.00151
C1    1    0.223672    0.716428    0.304407    11.00000    0.01939    0.02433 =
         0.01709   -0.00059    0.00113   -0.00127
C2    1    0.374898    0.654278    0.541314    11.00000    0.03002    0.02031 =
         0.01113   -0.00052    0.00273   -0.00089
C3    1    0.468251    0.626270    0.653003    11.00000    0.02563    0.02548 =
         0.02304   -0.00175    0.00043   -0.00016
AFIX  43
H3    2    0.536919    0.644330    0.612617    11.00000   -1.20000
AFIX   0
C4    1    0.456930    0.570754    0.826181    11.00000    0.02955    0.03032 =
         0.01945    0.00158    0.00013    0.00186
AFIX  43
H4    2    0.519177    0.550354    0.907997    11.00000   -1.20000
AFIX   0
C5    1    0.355670    0.544033    0.883303    11.00000    0.03563    0.02550 =
         0.02442    0.00070   -0.00302    0.00123
AFIX  43
H5    2    0.350629    0.505783    1.002330    11.00000   -1.20000
AFIX   0
C6    1    0.262958    0.572146    0.770149    11.00000    0.03144    0.02191 =
         0.02565    0.00131    0.00164   -0.00571
AFIX  43
H6    2    0.194139    0.554314    0.810809    11.00000   -1.20000
AFIX   0
C7    1    0.274543    0.627440    0.594870    11.00000    0.02265    0.02122 =
         0.02347   -0.00604   -0.00173    0.00016
C8    1    0.078390    0.643981    0.465087    11.00000    0.02552    0.02549 =
         0.04170    0.00271    0.00852   -0.00318
AFIX 137
H8A   2    0.072499    0.602313    0.567912    11.00000   -1.50000
H8B   2    0.050037    0.641243    0.249044    11.00000   -1.50000
H8C   2    0.036976    0.675440    0.585402    11.00000   -1.50000
AFIX   0
HKLF 4

REM  exp_3321 in Pna21 #33 (CF, yellow needle)
REM R1 =  0.0314 for    1890 Fo > 4sig(Fo)  and  0.0326 for all    1965 data
REM    119 parameters refined using      1 restraints

END

WGHT      0.0384      0.0000

REM Instructions for potential hydrogen bonds
EQIV $3 x+1/2, -y+3/2, z+1
HTAB C3 I1_$3
HTAB C6 Br1_$1
HTAB C8 Br1_$2

REM Highest difference peak  1.224,  deepest hole -1.013,  1-sigma level  0.151
Q1    1   0.2657  0.9146 -0.0366  11.00000  0.05    1.22
Q2    1   0.2721  0.8200 -0.0265  11.00000  0.05    1.04
Q3    1   0.3864  1.0108 -0.2085  11.00000  0.05    0.81
Q4    1   0.2785  0.8361 -0.2158  11.00000  0.05    0.62
Q5    1   0.3990  0.9131 -0.2162  11.00000  0.05    0.61
Q6    1   0.2794  0.9016  0.1516  11.00000  0.05    0.57
Q7    1   0.2612  0.9022 -0.2211  11.00000  0.05    0.57
Q8    1   0.2750  1.0022 -0.5498  11.00000  0.05    0.55
Q9    1   0.4238  0.8695 -0.0525  11.00000  0.05    0.53
Q10   1   0.3949  0.8774 -0.4340  11.00000  0.05    0.52
;
_shelx_res_checksum              70846

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_3_btt_ICl
_database_code_depnum_ccdc_archive 'CCDC 1034602'
_audit_update_record             
;
2014-11-17 deposited with the CCDC.
2015-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        '[(2(3)H-benzothiazole-thione)ICl] '
_chemical_name_common            '[(btt)ICl] '
_chemical_melting_point          410-412
_chemical_formula_moiety         'C7 H5 Cl I N S2'
_chemical_formula_sum            'C7 H5 Cl I N S2'
_chemical_formula_weight         329.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   4.02223(7)
_cell_length_b                   9.29376(17)
_cell_length_c                   25.2960(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     945.61(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7494
_cell_measurement_theta_min      5.0550
_cell_measurement_theta_max      76.6180

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.315
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.014
_exptl_absorpt_coefficient_mu    32.862
_shelx_estimated_absorpt_T_min   0.066
_shelx_estimated_absorpt_T_max   0.665
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7599
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS-2008/1

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   micro-source
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_reflns_number            10439
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.494
_diffrn_reflns_theta_max         77.029
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1990
_reflns_number_gt                1972
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'CrystaMaker (CrystalMaker Software ltd., 2012)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+0.5619P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.340(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1990
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0602
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
I1 I 0.84804(8) 0.68001(3) 0.19804(2) 0.01735(12) Uani 1 1 d . . . . .
Cl1 Cl 0.9981(4) 0.52992(14) 0.11043(5) 0.0232(3) Uani 1 1 d . . . . .
S1 S 0.6893(4) 0.83470(13) 0.27543(5) 0.0217(3) Uani 1 1 d . . . . .
S2 S 0.6910(4) 0.53419(13) 0.32454(5) 0.0194(3) Uani 1 1 d . . . . .
N1 N 0.4262(12) 0.7534(5) 0.36675(17) 0.0198(9) Uani 1 1 d . . . . .
H1 H 0.3540 0.8418 0.3716 0.024 Uiso 1 1 calc R U . . .
C1 C 0.5890(13) 0.7154(6) 0.3239(2) 0.0181(10) Uani 1 1 d . . . . .
C2 C 0.5061(15) 0.5141(6) 0.3868(2) 0.0194(10) Uani 1 1 d . . . . .
C3 C 0.4792(17) 0.3895(6) 0.4177(2) 0.0232(11) Uani 1 1 d . . . . .
H3 H 0.5692 0.3001 0.4064 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3145(17) 0.4032(7) 0.4658(2) 0.0271(12) Uani 1 1 d . . . . .
H4 H 0.2950 0.3211 0.4879 0.033 Uiso 1 1 calc R U . . .
C5 C 0.1771(17) 0.5330(7) 0.4825(2) 0.0256(11) Uani 1 1 d . . . . .
H5 H 0.0632 0.5372 0.5154 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2043(14) 0.6581(6) 0.4515(2) 0.0210(10) Uani 1 1 d . . . . .
H6 H 0.1107 0.7470 0.4626 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3755(14) 0.6456(6) 0.4037(2) 0.0186(10) Uani 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
I1 0.01711(17) 0.01432(16) 0.02062(16) 0.00049(10) 0.00129(11) -0.00075(12)
Cl1 0.0283(6) 0.0196(5) 0.0219(5) -0.0016(4) 0.0061(5) -0.0029(5)
S1 0.0299(7) 0.0139(5) 0.0213(5) 0.0001(4) 0.0029(5) 0.0008(6)
S2 0.0235(7) 0.0147(5) 0.0200(5) -0.0013(4) -0.0004(5) 0.0023(5)
N1 0.023(3) 0.015(2) 0.022(2) -0.0014(16) -0.0015(17) 0.0003(17)
C1 0.017(3) 0.017(2) 0.020(2) -0.0017(17) -0.0023(18) 0.0006(18)
C2 0.020(3) 0.018(2) 0.021(2) 0.0003(18) -0.003(2) -0.001(2)
C3 0.030(3) 0.017(2) 0.023(2) 0.0040(19) -0.008(2) 0.000(2)
C4 0.024(3) 0.031(3) 0.026(3) 0.008(2) -0.007(2) -0.005(3)
C5 0.025(3) 0.034(3) 0.019(2) 0.006(2) -0.002(2) -0.005(3)
C6 0.018(3) 0.025(3) 0.020(2) -0.0035(19) -0.004(2) 0.002(2)
C7 0.017(2) 0.020(2) 0.019(2) -0.0010(18) -0.002(2) 0.001(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
I1 S1 2.5114(12) . yes
I1 Cl1 2.6873(12) . yes
S1 C1 1.702(5) . yes
S2 C1 1.733(5) . yes
S2 C2 1.752(6) . yes
N1 C1 1.315(7) . yes
N1 C7 1.386(7) . yes
N1 H1 0.8800 . yes
C2 C7 1.397(7) . ?
C2 C3 1.402(7) . ?
C3 C4 1.390(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(8) . ?
C6 H6 0.9500 . ?

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
S1 I1 Cl1 175.65(4) . . ?
C1 S1 I1 104.40(18) . . ?
C1 S2 C2 90.7(3) . . ?
C1 N1 C7 115.8(5) . . ?
C1 N1 H1 122.1 . . ?
C7 N1 H1 122.1 . . ?
N1 C1 S1 122.4(4) . . ?
N1 C1 S2 111.8(4) . . ?
S1 C1 S2 125.7(3) . . ?
C7 C2 C3 121.5(5) . . ?
C7 C2 S2 110.0(4) . . ?
C3 C2 S2 128.5(4) . . ?
C4 C3 C2 116.7(6) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
C3 C4 C5 122.3(5) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 121.0(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 116.9(5) . . ?
C7 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
N1 C7 C6 126.6(5) . . ?
N1 C7 C2 111.8(5) . . ?
C6 C7 C2 121.6(5) . . ?

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
C7 N1 C1 S1 -177.3(4) . . . . ?
C7 N1 C1 S2 1.4(6) . . . . ?
I1 S1 C1 N1 -165.1(4) . . . . ?
I1 S1 C1 S2 16.4(4) . . . . ?
C2 S2 C1 N1 -0.9(4) . . . . ?
C2 S2 C1 S1 177.7(4) . . . . ?
C1 S2 C2 C7 0.3(4) . . . . ?
C1 S2 C2 C3 179.8(6) . . . . ?
C7 C2 C3 C4 0.4(9) . . . . ?
S2 C2 C3 C4 -179.1(5) . . . . ?
C2 C3 C4 C5 1.0(9) . . . . ?
C3 C4 C5 C6 -1.1(10) . . . . ?
C4 C5 C6 C7 -0.2(9) . . . . ?
C1 N1 C7 C6 -178.5(5) . . . . ?
C1 N1 C7 C2 -1.2(7) . . . . ?
C5 C6 C7 N1 178.6(5) . . . . ?
C5 C6 C7 C2 1.6(8) . . . . ?
C3 C2 C7 N1 -179.2(5) . . . . ?
S2 C2 C7 N1 0.4(6) . . . . ?
C3 C2 C7 C6 -1.8(9) . . . . ?
S2 C2 C7 C6 177.8(4) . . . . ?

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 H1 Cl1 0.88 2.30 3.138(5) 160.5 4_655

_refine_diff_density_max         1.485
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.127

_shelxl_version_number           2014-3

_shelx_res_file                  
;
TITL lk210314_1_2_a in P2(1)2(1)2(1) (CF, yellow plate)
CELL 1.54184 4.022233 9.293762 25.29598 90 90 90
ZERR 4 0.000067 0.000168 0.000462 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H N S Cl I
UNIT 28 20 4 8 4 4
EQIV $1 1-X,0.5+Y,0.5-Z
L.S. 6
PLAN  -10
SIZE 0.0135 0.072 0.1804
TEMP -153
HTAB N1 Cl1_$1
LIST 4
ACTA
MORE -1
BOND $H
HTAB 2.0
CONF
fmap 2 53
TWIN -1 0 0 0 -1 0 0 0 -1 2

WGHT    0.034300    0.561900
BASF   0.34045
FVAR       0.11811
I1    6    0.848044    0.680010    0.198039    11.00000    0.01711    0.01432 =
         0.02062    0.00049    0.00129   -0.00075
CL1   5    0.998149    0.529918    0.110433    11.00000    0.02827    0.01956 =
         0.02189   -0.00156    0.00613   -0.00291
S1    4    0.689315    0.834701    0.275431    11.00000    0.02990    0.01387 =
         0.02126    0.00010    0.00294    0.00082
S2    4    0.691002    0.534190    0.324544    11.00000    0.02352    0.01466 =
         0.01997   -0.00134   -0.00037    0.00234
N1    3    0.426204    0.753442    0.366748    11.00000    0.02277    0.01457 =
         0.02217   -0.00135   -0.00146    0.00026
AFIX  43
H1    2    0.354001    0.841825    0.371643    11.00000   -1.20000
AFIX   0
C1    1    0.589031    0.715364    0.323887    11.00000    0.01694    0.01718 =
         0.02025   -0.00166   -0.00228    0.00055
C2    1    0.506065    0.514095    0.386821    11.00000    0.01957    0.01783 =
         0.02077    0.00035   -0.00289   -0.00065
C3    1    0.479250    0.389456    0.417735    11.00000    0.02961    0.01743 =
         0.02265    0.00405   -0.00794   -0.00049
AFIX  43
H3    2    0.569173    0.300093    0.406420    11.00000   -1.20000
AFIX   0
C4    1    0.314545    0.403168    0.465757    11.00000    0.02407    0.03093 =
         0.02631    0.00765   -0.00710   -0.00507
AFIX  43
H4    2    0.294951    0.321133    0.487945    11.00000   -1.20000
AFIX   0
C5    1    0.177083    0.533045    0.482515    11.00000    0.02466    0.03360 =
         0.01853    0.00576   -0.00185   -0.00549
AFIX  43
H5    2    0.063222    0.537157    0.515384    11.00000   -1.20000
AFIX   0
C6    1    0.204340    0.658133    0.451511    11.00000    0.01793    0.02520 =
         0.01981   -0.00353   -0.00355    0.00204
AFIX  43
H6    2    0.110654    0.747004    0.462574    11.00000   -1.20000
AFIX   0
C7    1    0.375489    0.645575    0.403727    11.00000    0.01702    0.01978 =
         0.01909   -0.00096   -0.00173    0.00084
HKLF 4

REM  lk210314_1_2_a in P2(1)2(1)2(1) (CF, yellow plate)
REM R1 =  0.0239 for    1972 Fo > 4sig(Fo)  and  0.0242 for all    1990 data
REM    110 parameters refined using      0 restraints

END

WGHT      0.0343      0.5619

REM Instructions for potential hydrogen bonds
HTAB N1 Cl1_$1

REM Highest difference peak  1.485,  deepest hole -0.610,  1-sigma level  0.127
Q1    1   0.8443  0.6803  0.1612  11.00000  0.05    1.48
Q2    1   0.8491  0.6791  0.2366  11.00000  0.05    1.28
Q3    1   0.6411  0.7167  0.1974  11.00000  0.05    0.58
Q4    1   0.4009  0.8185  0.3004  11.00000  0.05    0.56
Q5    1   0.6772  0.5355  0.2860  11.00000  0.05    0.51
Q6    1   0.9831  0.5366  0.1361  11.00000  0.05    0.51
Q7    1   0.2324  0.8170  0.3000  11.00000  0.05    0.50
Q8    1   1.0752  0.6484  0.2012  11.00000  0.05    0.46
Q9    1   0.6246  0.6185  0.1898  11.00000  0.05    0.44
Q10   1   0.6681  0.8361  0.3176  11.00000  0.05    0.43
;
_shelx_res_checksum              19290

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_4_btt_IBr
_database_code_depnum_ccdc_archive 'CCDC 1034603'
_audit_update_record             
;
2014-11-17 deposited with the CCDC.
2015-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '[(2(3)H-benzothiazole-thione)IBr] '
_chemical_name_common            '[(btt)IBr] '
_chemical_melting_point          465-467
_chemical_formula_moiety         'C7 H5 Br I N S2'
_chemical_formula_sum            'C7 H5 Br I N S2'
_chemical_formula_weight         374.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   4.06180(9)
_cell_length_b                   9.44353(18)
_cell_length_c                   25.4237(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     975.20(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    15398
_cell_measurement_theta_min      4.9620
_cell_measurement_theta_max      76.6940

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.548
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.146
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    34.145
_shelx_estimated_absorpt_T_min   0.082
_shelx_estimated_absorpt_T_max   0.385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5559
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker, 2012)
Additional spherical absorption correction applied with mu*r =  0.2000
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21007
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         4.996
_diffrn_reflns_theta_max         77.130
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1992
_reflns_number_gt                1974
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'CrystaMaker (CrystalMaker Software ltd., 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
Refined as a 2-component inversion twin. The BASF value was
refined to 0.00738.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0079P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.007(5)
_chemical_absolute_configuration ab
_refine_ls_number_reflns         1992
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0152
_refine_ls_R_factor_gt           0.0149
_refine_ls_wR_factor_ref         0.0337
_refine_ls_wR_factor_gt          0.0336
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
I1 I 0.13928(6) 0.81526(2) 0.20000(2) 0.01869(7) Uani 1 1 d . . . . .
Br1 Br -0.03191(10) 0.95928(4) 0.10745(2) 0.02159(9) Uani 1 1 d . . . . .
S1 S 0.3090(3) 0.66493(9) 0.27805(3) 0.0228(2) Uani 1 1 d . . . . .
S2 S 0.3357(3) 0.96333(8) 0.32492(3) 0.02076(17) Uani 1 1 d . . . . .
N1 N 0.5902(9) 0.7457(3) 0.36739(11) 0.0208(6) Uani 1 1 d . . . . .
H1 H 0.658(16) 0.659(6) 0.3704(19) 0.031(13) Uiso 1 1 d . . . . .
C1 C 0.4239(10) 0.7842(4) 0.32473(13) 0.0199(8) Uani 1 1 d . . . . .
C2 C 0.5297(11) 0.9837(4) 0.38606(13) 0.0207(7) Uani 1 1 d . . . . .
C3 C 0.5680(11) 1.1060(4) 0.41592(14) 0.0232(8) Uani 1 1 d . . . . .
H3 H 0.4795 1.1941 0.4047 0.028 Uiso 1 1 calc R U . . .
C4 C 0.7409(12) 1.0940(4) 0.46277(15) 0.0279(9) Uani 1 1 d . . . . .
H4 H 0.7722 1.1760 0.4838 0.033 Uiso 1 1 calc R U . . .
C5 C 0.8710(12) 0.9643(4) 0.47996(13) 0.0259(8) Uani 1 1 d . . . . .
H5 H 0.9885 0.9601 0.5122 0.031 Uiso 1 1 calc R U . . .
C6 C 0.8300(11) 0.8411(4) 0.45019(13) 0.0236(7) Uani 1 1 d . . . . .
H6 H 0.9179 0.7529 0.4614 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6534(11) 0.8535(4) 0.40306(13) 0.0214(7) Uani 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
I1 0.01816(12) 0.01749(10) 0.02043(10) -0.00004(7) -0.00078(8) -0.00048(8)
Br1 0.0240(2) 0.01986(16) 0.02093(15) 0.00106(12) -0.00390(14) -0.00136(14)
S1 0.0299(6) 0.0172(3) 0.0213(3) 0.0008(3) -0.0028(3) 0.0003(4)
S2 0.0241(5) 0.0170(3) 0.0211(3) 0.0015(3) 0.0002(4) 0.0030(4)
N1 0.023(2) 0.0176(13) 0.0213(12) 0.0011(10) 0.0015(12) 0.0002(13)
C1 0.020(2) 0.0185(15) 0.0211(13) 0.0012(11) 0.0042(14) 0.0020(13)
C2 0.019(2) 0.0236(16) 0.0194(14) 0.0017(12) 0.0035(14) 0.0004(14)
C3 0.026(2) 0.0189(15) 0.0249(15) -0.0018(12) 0.0066(15) -0.0001(15)
C4 0.029(3) 0.0271(18) 0.0278(17) -0.0060(14) 0.0065(16) -0.0036(16)
C5 0.026(2) 0.0309(17) 0.0206(14) -0.0030(13) 0.0017(16) -0.0040(19)
C6 0.023(2) 0.0263(16) 0.0214(14) 0.0022(12) 0.0012(15) -0.0005(17)
C7 0.022(2) 0.0222(16) 0.0199(14) 0.0002(11) 0.0061(15) -0.0007(15)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 S1 2.5354(8) . yes
I1 Br1 2.8055(4) . yes
S1 C1 1.701(3) . yes
S2 C1 1.729(3) . yes
S2 C2 1.753(4) . yes
N1 C1 1.328(5) . yes
N1 C7 1.387(5) . yes
N1 H1 0.86(6) . ?
C2 C3 1.391(5) . ?
C2 C7 1.397(5) . ?
C3 C4 1.387(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(5) . ?
C6 H6 0.9500 . ?

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
S1 I1 Br1 174.45(2) . . ?
C1 S1 I1 104.47(12) . . ?
C1 S2 C2 90.97(17) . . ?
C1 N1 C7 115.3(3) . . ?
C1 N1 H1 120(4) . . ?
C7 N1 H1 125(4) . . ?
N1 C1 S1 121.9(3) . . ?
N1 C1 S2 111.8(3) . . ?
S1 C1 S2 126.3(2) . . ?
C3 C2 C7 121.5(3) . . ?
C3 C2 S2 128.7(3) . . ?
C7 C2 S2 109.8(3) . . ?
C4 C3 C2 117.2(4) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 117.0(4) . . ?
C5 C6 H6 121.5 . . ?
C7 C6 H6 121.5 . . ?
N1 C7 C2 112.2(3) . . ?
N1 C7 C6 126.3(3) . . ?
C2 C7 C6 121.5(3) . . ?

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
C7 N1 C1 S1 -177.2(3) . . . . ?
C7 N1 C1 S2 1.0(5) . . . . ?
I1 S1 C1 N1 -166.2(3) . . . . ?
I1 S1 C1 S2 15.9(3) . . . . ?
C2 S2 C1 N1 -0.8(3) . . . . ?
C2 S2 C1 S1 177.3(3) . . . . ?
C1 S2 C2 C3 -179.9(4) . . . . ?
C1 S2 C2 C7 0.4(3) . . . . ?
C7 C2 C3 C4 1.4(6) . . . . ?
S2 C2 C3 C4 -178.3(3) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C4 C5 C6 C7 -0.3(7) . . . . ?
C1 N1 C7 C2 -0.7(5) . . . . ?
C1 N1 C7 C6 -178.4(4) . . . . ?
C3 C2 C7 N1 -179.7(4) . . . . ?
S2 C2 C7 N1 0.1(5) . . . . ?
C3 C2 C7 C6 -1.9(6) . . . . ?
S2 C2 C7 C6 177.9(3) . . . . ?
C5 C6 C7 N1 178.7(4) . . . . ?
C5 C6 C7 C2 1.3(6) . . . . ?

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
_geom_hbond_publ_flag
N1 H1 Br1 0.86(6) 2.49(6) 3.308(3) 159(5) 4_645 yes

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.083

_shelx_res_file                  
;

    lkibr120.res created by SHELXL-2014/7


TITL lkibr120 in P212121 #19 (yellow needle)
CELL 1.54178 4.061798 9.443532 25.423706 90 90 90
ZERR 4 0.000089 0.000181 0.000447 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H N S Br I
UNIT 28 20 4 8 4 4
L.S. 6
LIST 4
ACTA
HTAB 2.0
OMIT 0 0 2
OMIT 2 10 12
PLAN -10
TEMP -153
SIZE 0.0345 0.0404 0.1460
BOND $H
MORE -1
EQIV $1 -x+1, y-1/2, -z+1/2
HTAB N1 Br1_$1
EQIV $2 -x+1, y+1/2, -z+1/2
HTAB C3 I1_$2
EQIV $3 -x, y+1/2, -z+1/2
HTAB C3 Br1_$3
TWIN
CONF
fmap 2 53
WGHT    0.007900
BASF   0.00738
FVAR       0.11848
I1    6    0.139279    0.815255    0.200004    11.00000    0.01816    0.01749 =
         0.02043   -0.00004   -0.00078   -0.00048
BR1   5   -0.031911    0.959284    0.107445    11.00000    0.02397    0.01986 =
         0.02093    0.00106   -0.00390   -0.00136
S1    4    0.309028    0.664932    0.278053    11.00000    0.02988    0.01721 =
         0.02129    0.00076   -0.00282    0.00025
S2    4    0.335730    0.963329    0.324918    11.00000    0.02415    0.01699 =
         0.02114    0.00151    0.00015    0.00303
N1    3    0.590225    0.745697    0.367394    11.00000    0.02342    0.01764 =
         0.02128    0.00110    0.00147    0.00021
H1   2    0.658414    0.659497    0.370406    11.00000    0.03148
C1    1    0.423946    0.784188    0.324734    11.00000    0.02016    0.01850 =
         0.02108    0.00122    0.00421    0.00202
C2    1    0.529682    0.983749    0.386060    11.00000    0.01897    0.02362 =
         0.01942    0.00173    0.00345    0.00044
C3    1    0.568009    1.106050    0.415919    11.00000    0.02569    0.01888 =
         0.02494   -0.00185    0.00657   -0.00014
AFIX  43
H3    2    0.479493    1.194132    0.404701    11.00000   -1.20000
AFIX   0
C4    1    0.740898    1.094041    0.462768    11.00000    0.02875    0.02707 =
         0.02780   -0.00605    0.00647   -0.00359
AFIX  43
H4    2    0.772178    1.176018    0.483841    11.00000   -1.20000
AFIX   0
C5    1    0.871047    0.964257    0.479959    11.00000    0.02632    0.03086 =
         0.02064   -0.00301    0.00166   -0.00396
AFIX  43
H5    2    0.988487    0.960123    0.512237    11.00000   -1.20000
AFIX   0
C6    1    0.829975    0.841131    0.450185    11.00000    0.02323    0.02625 =
         0.02141    0.00219    0.00122   -0.00049
AFIX  43
H6    2    0.917866    0.752928    0.461397    11.00000   -1.20000
AFIX   0
C7    1    0.653397    0.853530    0.403055    11.00000    0.02224    0.02221 =
         0.01988    0.00023    0.00608   -0.00072
HKLF 4

REM  lkibr120 in P212121 #19 (yellow needle)
REM R1 =  0.0149 for    1974 Fo > 4sig(Fo)  and  0.0152 for all    1992 data
REM    114 parameters refined using      0 restraints

END

WGHT      0.0079      0.0000

REM Instructions for potential hydrogen bonds
HTAB N1 Br1_$1
HTAB C3 I1_$2
HTAB C3 Br1_$3

REM Highest difference peak  0.328,  deepest hole -0.444,  1-sigma level  0.083
Q1    1  -0.1595  0.6631  0.2378  11.00000  0.05    0.33
Q2    1   0.1100  0.9378  0.1412  11.00000  0.05    0.31
Q3    1   0.0081  0.7407  0.1598  11.00000  0.05    0.30
Q4    1   0.6118  0.7963  0.2008  11.00000  0.05    0.29
Q5    1   0.3899  1.0208  0.1856  11.00000  0.05    0.28
Q6    1   0.4825  0.8833  0.1368  11.00000  0.05    0.26
Q7    1   0.4818  0.7610  0.1385  11.00000  0.05    0.26
Q8    1  -0.1792  0.8083  0.2622  11.00000  0.05    0.26
Q9    1   0.2163  0.8193  0.0570  11.00000  0.05    0.26
Q10   1   1.0951  0.8194  0.3998  11.00000  0.05    0.25
;
_shelx_res_checksum              75096

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: tetrahydrofuran/dichloromethane'
_chemical_properties_physical    Heat-sensitive
