#------------------------------------------------------------------------------
#$Date: 2016-03-26 23:04:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180528 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/97/7219720.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7219720
loop_
_publ_author_name
'Koskinen, L.'
'Hirva, P.'
'Hasu, A.'
'Jääskeläinen, S.'
'Koivistoinen, J.'
'Pettersson, M.'
'Haukka, M.'
_publ_section_title
;
 Modification of the supramolecular structure of [(thione)IY] (Y = Cl, Br)
 systems by cooperation of strong halogen bonds and hydrogen bonds
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              2718
_journal_paper_doi               10.1039/C4CE02449D
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C7 H5 Cl I N S2'
_chemical_formula_sum            'C7 H5 Cl I N S2'
_chemical_formula_weight         329.59
_chemical_melting_point          411.0(10)
_chemical_name_common            '[(btt)ICl] '
_chemical_name_systematic        '[(2(3)H-benzothiazole-thione)ICl] '
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2014-11-17 deposited with the CCDC.
2015-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.02223(7)
_cell_length_b                   9.29376(17)
_cell_length_c                   25.2960(5)
_cell_measurement_reflns_used    7494
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      76.6180
_cell_measurement_theta_min      5.0550
_cell_volume                     945.61(3)
_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_collection
;
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_molecular_graphics
'CrystaMaker (CrystalMaker Software ltd., 2012)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10439
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.029
_diffrn_reflns_theta_min         3.494
_diffrn_source                   micro-source
_exptl_absorpt_coefficient_mu    32.862
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7599
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.315
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.014
_refine_diff_density_max         1.485
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.340(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0343P)²+0.5619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0605
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1972
_reflns_number_total             1990
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce02449d2.cif
_cod_data_source_block           3_btt_ICl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '410-412' was changed to '411.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3086 2015-02-26 13:12:21Z robertas 

 Adding full bibliography for 7219718--7219721.cif.
;
_cod_database_code               7219720
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min   0.066
_shelx_estimated_absorpt_t_max   0.665
_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
#END Tags that were not found in dictionaries
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'
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
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)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_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_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
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
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)
