




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813015742/hb7089sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536813015742/hb7089Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813015742/hb7089Isup3.cml |
CCDC reference: 961817
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean
(C-C) = 0.008 Å
- R factor = 0.063
- wR factor = 0.134
- Data-to-parameter ratio = 18.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.951
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0076 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C12 H14 N2 S2 PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.198 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 81 PLAT915_ALERT_3_C Low Friedel Pair Coverage ...................... 67 %
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 6 PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? Do ! PLAT007_ALERT_5_G Note: Number of Unrefined Donor-H Atoms ........ 6 PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 3 Cl PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 4 H2 O PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 5 H2 O PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6 PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 91
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
2-Aminobenzenethiol (0.1 mmol) was added to concentrated HCl (2 ml) and transfered into a 23 ml teflon-lined stainless steel autoclave and heated at 120° C for 3 days. Then the autoclave was cooled to room temperature at 10°/h. Colourless prisms were collected, washed with ethanol and dried in air at room temperature.
Approximate positions for all H atoms were first obtained from the difference electron density map. However, the H atoms were situated into idealized positions and the H-atoms have been refined within the riding atom approximation. The applied constraints were as follow: Caryl—Haryl = 0.93 Å and Nammonium—Hammonium = 0.89 Å. Uiso(Haryl) = 1.2Ueq(Caryl). Uiso(Hammonium) = 1.5Ueq(Cammonium). Except for H1W, H2W, H3W and H4W (of water molecule) were located in a difference Fourier map and refined isotropically with Uiso(H) = 1.5Ueq(O).
As part of our ongoing studies on the synthesis, structures and biological activity of organometallic complexes based in sulfur (Benmebarek et al. 2012 and Benmebarek et al. 2013), we have synthesized and determined the crystal structure of the title compound (I), (Fig. 1). In the cation the S—S bond length is 2.061 (2)°, indicating the single bond character similar to that found in 4,4'-diaminophenyldisulfide (Tang et al., 2011; Goh et al. 2010). In the diprotoned 2,2'-dithiodianiline moiety, the dihedral angle between the benzene rings is 9.03 (17)°; different to that found in [67.82 (9)°] 1,2-Bis(2-nitrophenyl)disulfane (Song & Fan, 2009) and [39.9 (2)°]4,4'- diaminophenyldisulfide (Tang et al., 2011). The crystal packing can be described as alternating layers parallel to (100) plane, wich are linked toghether by N—H···Cl and N—H···O interactions involving molecule of water and anions chloride. O—H···Cl hydrogen bond and π–π stacking are observed.
For related structures and background to disulfides, see: Benmebarek et al. (2012, 2013). For related structures, see: Tang et al. (2011); Goh et al. (2010); Song & Fan (2009).
Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012).
![]() | Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. |
![]() | Fig. 2. Diagram packing of (I) viwed via c axis showing hydrogen bonding in alterning layers. |
C12H14N2S22+·2Cl−·2H2O | F(000) = 744 |
Mr = 357.32 | Dx = 1.4 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 2698 reflections |
a = 17.826 (7) Å | θ = 2.3–28.5° |
b = 13.358 (5) Å | µ = 0.63 mm−1 |
c = 7.120 (3) Å | T = 150 K |
V = 1695.4 (12) Å3 | Prism, colourless |
Z = 4 | 0.16 × 0.13 × 0.11 mm |
Bruker APEXII CCD diffractometer | 2409 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.097 |
Graphite monochromator | θmax = 28.8°, θmin = 2.8° |
φ and ω scans | h = −24→23 |
10760 measured reflections | k = −18→18 |
3584 independent reflections | l = −9→8 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0595P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3584 reflections | Δρmax = 0.58 e Å−3 |
195 parameters | Δρmin = −0.47 e Å−3 |
6 restraints | Absolute structure: Flack (1983), 1369 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.12 (12) |
C12H14N2S22+·2Cl−·2H2O | V = 1695.4 (12) Å3 |
Mr = 357.32 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 17.826 (7) Å | µ = 0.63 mm−1 |
b = 13.358 (5) Å | T = 150 K |
c = 7.120 (3) Å | 0.16 × 0.13 × 0.11 mm |
Bruker APEXII CCD diffractometer | 2409 reflections with I > 2σ(I) |
10760 measured reflections | Rint = 0.097 |
3584 independent reflections |
R[F2 > 2σ(F2)] = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.134 | Δρmax = 0.58 e Å−3 |
S = 1.05 | Δρmin = −0.47 e Å−3 |
3584 reflections | Absolute structure: Flack (1983), 1369 Friedel pairs |
195 parameters | Absolute structure parameter: −0.12 (12) |
6 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl2 | 0.98060 (6) | 0.10914 (8) | 1.19390 (17) | 0.0269 (3) | |
S1 | 0.86675 (9) | −0.10667 (11) | 1.3286 (2) | 0.0412 (4) | |
Cl1 | 0.99242 (8) | 0.36455 (10) | 0.7389 (2) | 0.0411 (4) | |
S2 | 0.85864 (8) | −0.15845 (11) | 1.0567 (2) | 0.0395 (4) | |
O2W | 0.9096 (2) | 0.1819 (3) | 1.5764 (6) | 0.0381 (10) | |
H3W | 0.935 (3) | 0.233 (3) | 1.609 (9) | 0.057* | |
H4W | 0.937 (3) | 0.150 (4) | 1.497 (7) | 0.057* | |
N2 | 0.8933 (2) | 0.0331 (3) | 0.8354 (6) | 0.0267 (9) | |
H2A | 0.8991 | 0.0831 | 0.7542 | 0.04* | |
H2B | 0.9208 | −0.019 | 0.7989 | 0.04* | |
H2C | 0.9082 | 0.0528 | 0.9489 | 0.04* | |
C21 | 0.7911 (3) | −0.0781 (4) | 0.9473 (8) | 0.0286 (12) | |
O1W | 1.0599 (3) | 0.4223 (3) | 1.3483 (6) | 0.0534 (12) | |
H1W | 1.043 (4) | 0.476 (3) | 1.302 (9) | 0.08* | |
H2W | 1.039 (4) | 0.406 (4) | 1.453 (6) | 0.08* | |
N1 | 0.9146 (2) | −0.2839 (3) | 1.5749 (6) | 0.0282 (10) | |
H1A | 0.9242 | −0.3284 | 1.6647 | 0.042* | |
H1B | 0.9388 | −0.2271 | 1.5996 | 0.042* | |
H1C | 0.9298 | −0.3079 | 1.4647 | 0.042* | |
C26 | 0.8140 (2) | 0.0039 (3) | 0.8427 (7) | 0.0218 (10) | |
C14 | 0.7102 (3) | −0.3103 (4) | 1.6647 (8) | 0.0317 (12) | |
H14 | 0.6782 | −0.3509 | 1.7342 | 0.038* | |
C12 | 0.7275 (3) | −0.1730 (4) | 1.4523 (8) | 0.0332 (13) | |
H12 | 0.7073 | −0.1212 | 1.3811 | 0.04* | |
C25 | 0.7627 (3) | 0.0625 (3) | 0.7478 (8) | 0.0272 (11) | |
H25 | 0.7787 | 0.1168 | 0.6768 | 0.033* | |
C15 | 0.7858 (3) | −0.3249 (3) | 1.6726 (7) | 0.0268 (11) | |
H15 | 0.8055 | −0.3753 | 1.7482 | 0.032* | |
C11 | 0.8050 (3) | −0.1876 (3) | 1.4566 (7) | 0.0255 (11) | |
C23 | 0.6638 (3) | −0.0391 (4) | 0.8641 (8) | 0.0395 (14) | |
H23 | 0.6128 | −0.0526 | 0.8741 | 0.047* | |
C24 | 0.6876 (3) | 0.0396 (4) | 0.7590 (8) | 0.0345 (12) | |
H24 | 0.6528 | 0.0784 | 0.6943 | 0.041* | |
C16 | 0.8335 (3) | −0.2645 (3) | 1.5676 (7) | 0.0237 (10) | |
C13 | 0.6811 (3) | −0.2350 (4) | 1.5534 (8) | 0.0381 (13) | |
H13 | 0.6294 | −0.2262 | 1.5468 | 0.046* | |
C22 | 0.7156 (3) | −0.1002 (4) | 0.9572 (8) | 0.0354 (13) | |
H22 | 0.6992 | −0.1554 | 1.0255 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl2 | 0.0198 (5) | 0.0332 (6) | 0.0276 (7) | −0.0025 (5) | −0.0034 (6) | 0.0026 (5) |
S1 | 0.0445 (9) | 0.0428 (7) | 0.0364 (8) | −0.0186 (7) | −0.0119 (8) | 0.0133 (6) |
Cl1 | 0.0422 (8) | 0.0424 (7) | 0.0388 (9) | −0.0023 (5) | −0.0125 (7) | 0.0027 (6) |
S2 | 0.0429 (8) | 0.0445 (7) | 0.0310 (8) | 0.0133 (6) | 0.0111 (8) | 0.0111 (6) |
O2W | 0.040 (2) | 0.043 (2) | 0.031 (3) | −0.0078 (17) | −0.002 (2) | 0.0002 (18) |
N2 | 0.029 (2) | 0.030 (2) | 0.021 (2) | 0.0051 (16) | −0.001 (2) | −0.0027 (17) |
C21 | 0.034 (3) | 0.032 (3) | 0.019 (3) | 0.001 (2) | 0.004 (3) | −0.007 (2) |
O1W | 0.072 (3) | 0.051 (3) | 0.038 (3) | 0.019 (2) | 0.003 (3) | −0.003 (2) |
N1 | 0.030 (2) | 0.030 (2) | 0.025 (3) | −0.0031 (17) | 0.000 (2) | −0.0016 (18) |
C26 | 0.022 (2) | 0.028 (2) | 0.015 (3) | 0.0005 (18) | 0.003 (2) | −0.0089 (19) |
C14 | 0.028 (3) | 0.044 (3) | 0.023 (3) | −0.007 (2) | 0.002 (3) | −0.004 (2) |
C12 | 0.038 (3) | 0.035 (3) | 0.027 (3) | 0.004 (2) | −0.002 (3) | −0.006 (2) |
C25 | 0.030 (3) | 0.030 (2) | 0.021 (3) | 0.005 (2) | −0.003 (3) | −0.006 (2) |
C15 | 0.033 (3) | 0.026 (2) | 0.021 (3) | −0.0076 (19) | 0.000 (3) | −0.0043 (19) |
C11 | 0.030 (3) | 0.028 (2) | 0.019 (3) | −0.008 (2) | 0.002 (2) | −0.006 (2) |
C23 | 0.026 (3) | 0.062 (4) | 0.030 (4) | −0.006 (3) | 0.002 (3) | −0.015 (3) |
C24 | 0.027 (3) | 0.046 (3) | 0.030 (3) | 0.005 (2) | −0.008 (3) | −0.008 (2) |
C16 | 0.024 (2) | 0.027 (2) | 0.020 (3) | −0.0046 (18) | 0.001 (2) | −0.010 (2) |
C13 | 0.024 (3) | 0.052 (3) | 0.038 (4) | 0.000 (2) | 0.009 (3) | −0.017 (3) |
C22 | 0.030 (3) | 0.049 (3) | 0.028 (3) | −0.008 (3) | 0.005 (3) | −0.003 (2) |
S1—C11 | 1.792 (5) | C14—C15 | 1.364 (6) |
S1—S2 | 2.061 (2) | C14—C13 | 1.380 (8) |
S2—C21 | 1.791 (5) | C14—H14 | 0.93 |
O2W—H3W | 0.86 (2) | C12—C13 | 1.375 (8) |
O2W—H4W | 0.86 (2) | C12—C11 | 1.396 (7) |
N2—C26 | 1.468 (6) | C12—H12 | 0.93 |
N2—H2A | 0.89 | C25—C24 | 1.375 (7) |
N2—H2B | 0.89 | C25—H25 | 0.93 |
N2—H2C | 0.89 | C15—C16 | 1.391 (7) |
C21—C22 | 1.380 (7) | C15—H15 | 0.93 |
C21—C26 | 1.386 (7) | C11—C16 | 1.391 (7) |
O1W—H1W | 0.852 (19) | C23—C24 | 1.358 (8) |
O1W—H2W | 0.858 (19) | C23—C22 | 1.399 (8) |
N1—C16 | 1.469 (6) | C23—H23 | 0.93 |
N1—H1A | 0.89 | C24—H24 | 0.93 |
N1—H1B | 0.89 | C13—H13 | 0.93 |
N1—H1C | 0.89 | C22—H22 | 0.93 |
C26—C25 | 1.380 (7) | ||
C11—S1—S2 | 103.43 (17) | C13—C12—H12 | 120 |
C21—S2—S1 | 104.74 (18) | C11—C12—H12 | 120 |
H3W—O2W—H4W | 106 (6) | C24—C25—C26 | 119.4 (5) |
C26—N2—H2A | 109.5 | C24—C25—H25 | 120.3 |
C26—N2—H2B | 109.5 | C26—C25—H25 | 120.3 |
H2A—N2—H2B | 109.5 | C14—C15—C16 | 119.9 (5) |
C26—N2—H2C | 109.5 | C14—C15—H15 | 120 |
H2A—N2—H2C | 109.5 | C16—C15—H15 | 120 |
H2B—N2—H2C | 109.5 | C16—C11—C12 | 118.5 (4) |
C22—C21—C26 | 118.9 (5) | C16—C11—S1 | 120.7 (4) |
C22—C21—S2 | 120.3 (4) | C12—C11—S1 | 120.8 (4) |
C26—C21—S2 | 120.6 (4) | C24—C23—C22 | 120.4 (5) |
H1W—O1W—H2W | 114 (3) | C24—C23—H23 | 119.8 |
C16—N1—H1A | 109.5 | C22—C23—H23 | 119.8 |
C16—N1—H1B | 109.5 | C23—C24—C25 | 120.5 (5) |
H1A—N1—H1B | 109.5 | C23—C24—H24 | 119.7 |
C16—N1—H1C | 109.5 | C25—C24—H24 | 119.7 |
H1A—N1—H1C | 109.5 | C15—C16—C11 | 120.7 (4) |
H1B—N1—H1C | 109.5 | C15—C16—N1 | 118.7 (4) |
C25—C26—C21 | 121.0 (4) | C11—C16—N1 | 120.6 (4) |
C25—C26—N2 | 118.1 (4) | C12—C13—C14 | 120.9 (5) |
C21—C26—N2 | 120.8 (4) | C12—C13—H13 | 119.5 |
C15—C14—C13 | 120.0 (5) | C14—C13—H13 | 119.5 |
C15—C14—H14 | 120 | C21—C22—C23 | 119.6 (5) |
C13—C14—H14 | 120 | C21—C22—H22 | 120.2 |
C13—C12—C11 | 120.0 (5) | C23—C22—H22 | 120.2 |
C11—S1—S2—C21 | 96.8 (2) | C22—C23—C24—C25 | −2.1 (8) |
S1—S2—C21—C22 | −87.5 (5) | C26—C25—C24—C23 | 0.7 (8) |
S1—S2—C21—C26 | 96.2 (4) | C14—C15—C16—C11 | 1.2 (7) |
C22—C21—C26—C25 | −0.7 (8) | C14—C15—C16—N1 | −178.3 (4) |
S2—C21—C26—C25 | 175.7 (4) | C12—C11—C16—C15 | −0.3 (7) |
C22—C21—C26—N2 | 177.1 (4) | S1—C11—C16—C15 | 177.5 (4) |
S2—C21—C26—N2 | −6.5 (6) | C12—C11—C16—N1 | 179.1 (4) |
C21—C26—C25—C24 | 0.7 (7) | S1—C11—C16—N1 | −3.0 (6) |
N2—C26—C25—C24 | −177.1 (5) | C11—C12—C13—C14 | 2.1 (8) |
C13—C14—C15—C16 | −0.4 (7) | C15—C14—C13—C12 | −1.2 (8) |
C13—C12—C11—C16 | −1.3 (7) | C26—C21—C22—C23 | −0.8 (8) |
C13—C12—C11—S1 | −179.1 (4) | S2—C21—C22—C23 | −177.2 (4) |
S2—S1—C11—C16 | 103.3 (4) | C24—C23—C22—C21 | 2.2 (9) |
S2—S1—C11—C12 | −78.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1Wi | 0.89 | 1.83 | 2.723 (6) | 178 |
N1—H1B···Cl2i | 0.89 | 2.24 | 3.108 (4) | 166 |
N1—H1C···Cl1i | 0.89 | 2.25 | 3.103 (4) | 160 |
N2—H2A···O2Wii | 0.89 | 1.84 | 2.727 (6) | 177 |
N2—H2B···Cl2iii | 0.89 | 2.26 | 3.111 (4) | 160 |
N2—H2C···Cl2 | 0.89 | 2.30 | 3.157 (4) | 163 |
O2W—H4W···Cl2 | 0.86 (5) | 2.36 (5) | 3.157 (5) | 155 (5) |
O2W—H3W···Cl1iv | 0.85 (5) | 2.23 (5) | 3.078 (4) | 171 (6) |
O1W—H1W···Cl1v | 0.85 (5) | 2.27 (5) | 3.096 (5) | 167 (5) |
O1W—H2W···Cl1iv | 0.86 (5) | 2.27 (5) | 3.127 (5) | 176 (7) |
Symmetry codes: (i) −x+2, −y, z+1/2; (ii) x, y, z−1; (iii) −x+2, −y, z−1/2; (iv) x, y, z+1; (v) −x+2, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C12H14N2S22+·2Cl−·2H2O |
Mr | 357.32 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 150 |
a, b, c (Å) | 17.826 (7), 13.358 (5), 7.120 (3) |
V (Å3) | 1695.4 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.63 |
Crystal size (mm) | 0.16 × 0.13 × 0.11 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10760, 3584, 2409 |
Rint | 0.097 |
(sin θ/λ)max (Å−1) | 0.678 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.134, 1.05 |
No. of reflections | 3584 |
No. of parameters | 195 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.58, −0.47 |
Absolute structure | Flack (1983), 1369 Friedel pairs |
Absolute structure parameter | −0.12 (12) |
Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 2012).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1Wi | 0.89 | 1.83 | 2.723 (6) | 178 |
N1—H1B···Cl2i | 0.89 | 2.24 | 3.108 (4) | 166 |
N1—H1C···Cl1i | 0.89 | 2.25 | 3.103 (4) | 160 |
N2—H2A···O2Wii | 0.89 | 1.84 | 2.727 (6) | 177 |
N2—H2B···Cl2iii | 0.89 | 2.26 | 3.111 (4) | 160 |
N2—H2C···Cl2 | 0.89 | 2.30 | 3.157 (4) | 163 |
O2W—H4W···Cl2 | 0.86 (5) | 2.36 (5) | 3.157 (5) | 155 (5) |
O2W—H3W···Cl1iv | 0.85 (5) | 2.23 (5) | 3.078 (4) | 171 (6) |
O1W—H1W···Cl1v | 0.85 (5) | 2.27 (5) | 3.096 (5) | 167 (5) |
O1W—H2W···Cl1iv | 0.86 (5) | 2.27 (5) | 3.127 (5) | 176 (7) |
Symmetry codes: (i) −x+2, −y, z+1/2; (ii) x, y, z−1; (iii) −x+2, −y, z−1/2; (iv) x, y, z+1; (v) −x+2, −y+1, z+1/2. |
As part of our ongoing studies on the synthesis, structures and biological activity of organometallic complexes based in sulfur (Benmebarek et al. 2012 and Benmebarek et al. 2013), we have synthesized and determined the crystal structure of the title compound (I), (Fig. 1). In the cation the S—S bond length is 2.061 (2)°, indicating the single bond character similar to that found in 4,4'-diaminophenyldisulfide (Tang et al., 2011; Goh et al. 2010). In the diprotoned 2,2'-dithiodianiline moiety, the dihedral angle between the benzene rings is 9.03 (17)°; different to that found in [67.82 (9)°] 1,2-Bis(2-nitrophenyl)disulfane (Song & Fan, 2009) and [39.9 (2)°]4,4'- diaminophenyldisulfide (Tang et al., 2011). The crystal packing can be described as alternating layers parallel to (100) plane, wich are linked toghether by N—H···Cl and N—H···O interactions involving molecule of water and anions chloride. O—H···Cl hydrogen bond and π–π stacking are observed.