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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2400
https://doi.org/10.1107/S1600536812029765

N-[2-(Methyl­sulfan­yl)phen­yl]-2-sulfanylbenzamide

Chang-Chih Hsieh,a Hon Man Leea and Yih-Chern Hornga*

aNational Changhua University of Education, Department of Chemistry, Changhua, Taiwan 50058
*Correspondence e-mail: ychorng@cc.ncue.edu.tw

(Received 8 June 2012; accepted 29 June 2012; online 10 July 2012)

In the title compound, C14H13NOS2, the S atom with the methyl group is involved in an intra­molecular hydrogen bond with the amido H atom. In the crystal, the sulfanyl H atoms form inter­molecular hydrogen bonds with the O atoms, connecting the mol­ecules into zigzag chains along the c axis. The two aromatic rings exhibit a small interplanar angle of 16.03 (9)°.

Related literature

For organic and inorganic supramolecules with dynamic covalent bonds: see Huang et al. (2012[Huang, P.-S., Kuo, C.-H., Hsieh, C.-C. & Horng, Y.-C. (2012). Chem. Commun. 48, 3227-3229.]); Wu et al. (2012[Wu, Z.-S., Hsu, J.-T., Hsieh, C.-C. & Horng, Y.-C. (2012). Chem. Commun. 48, 3436-3438.]). For aromatic amides with N—H⋯S inter­actions: see Du et al. (2009[Du, P., Jiang, X.-K. & Li, Z.-T. (2009). Tetrahedron Lett. 50, 320-324.])

[Scheme 1]

Experimental

Crystal data

  • C14H13NOS2

  • Mr = 275.37

  • Monoclinic, P 21 /c

  • a = 7.9549 (5) Å

  • b = 22.7530 (14) Å

  • c = 8.0966 (5) Å

  • β = 118.787 (1)°

  • V = 1284.36 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.40 mm−1

  • T = 150 K

  • 0.49 × 0.12 × 0.08 mm
Data collection

  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.828, Tmax = 0.969

  • 14799 measured reflections

  • 3196 independent reflections

  • 2577 reflections with I > 2σ

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.108

  • S = 1.07

  • 3196 reflections

  • 172 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H8⋯S1 0.83 (2) 2.49 (2) 2.9150 (14) 112.7 (17)
S2—H13⋯O1i 1.24 (3) 2.37 (3) 3.5976 (14) 169.5 (17)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812029765/ds2201sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029765/ds2201Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029765/ds2201Isup3.cml

checkCIF report


Comment top

The N—H···S hydrogen bonding interactions are quite often found in proteins, where the sulfur atoms are ususally from cysteine or methionine residues. Many organic compounds containing amide and thiol (or thioether) moieties were investigated to give a deep insight of the N—H···S hydrogen bonding interactions (Du et al. 2009), which may help to understand protein folding processes and enzymatic catalyses. Our group is interesting in the preparation and encapsulation behaviors of organic and inorganic supramolecules with dynamic covalent bonds (Huang et al. 2012; Wu et al. 2012). The title compound is a sulfur-containing secondary amide with two aryl groups. We synthesized and report its structure here, and will atempt to use it as a building block for the construction of more complex organic or inorganic molecules with unique properties.

The title compound crystallizes in the monoclinic space group P 21/c. Fig. 1. shows a displacement ellipsoid plot of the compound. The S—C(sp3) bond distane of 1.7876 (19) Å is slightly longer than those of the S—C(sp2) bonds [1.7678 (17) and 1.7708 (17) Å]. The two aromatic rings (C2 to C7) and (C9 to C14) exhibit a small interplanar angle of 16.03 (9) °. Both classical and non-classical hydrogen bonds are present (Table 1). The S atom with the Me group involves in an intramolecular hydrogen bond with the amido H-atom [N···S = 2.9150 (14) Å]. A non-classical intramolecular hydrogen bond of the type C—H···O also exists [C···O = 2.949 (2) Å]. In the crystal structure, the H atoms upon S atoms form intermolecular hydrogen bonds with the O atoms [S···O = 3.5976 (14) Å], connecting the compounds into zigzag chains along the c axis (Fig. 2).

Related literature top

For reversible organic and inorganic molecules with dynamic covalent bonds: see Huang et al. (2012); Wu et al. (2012). For aromatic amides with N—H···S interactions: see Du et al. (2009)

Experimental top

A CH2Cl2 solution (20 ml) containing 2-methylthioaniline (1.39 g, 10 mmol) and NEt3 (1.02 g, 10 mmol) was mixed with another CH2Cl2 solution (20 ml) containing 2,2'-dithiosalicyl chloride (1.7 g, 5 mmol). After stirred at room temperature for 12 h, the mixture was washed with saturated NaHCO3 solution and distilled water. The combined CH2Cl2 portions were collected and dried with anhydrous MgSO4. The solvent was then removed under vacuum to afford a yellow powder. An uncapped 50 ml flask, containing the yellow solid and an excess NaBH4 (0.33 g, 9 mmol), was placed in an ice-water bath. To this flask, 25 ml of MeOH was added slowly. After the resulting mixture stirred at 4°C for 10 minutes, the water bath was removed and the stirring was continued for another 30 minutes. The yellowish mixture was added dropwise with concentrated HCl(aq) to quench excess NaBH4. After completion, the solution was extracted with CH2Cl2 and distilled water. The collected CH2Cl2 fractions were dried over anhydrous MgSO4, filtered, and vacuum dried to give 2.03 g of light-yellow solid (86% yield). Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of THF solution of the compound at -4°C.

Refinement top

The H on C atoms were positioned geometrically and refined as riding atoms, with Caryl—H = 0.93 and Cmethyl—H = 0.96 Å while Uiso(H) = 1.2Ueq (Caryl) and 1.5Ueq (Cmethyl). The H on N and S atoms were located from the difference Fourier map and freely refined (N1—H8 = 0.83 (2) Å and S2—H13 = 1.24 (3) Å).

Structure description top

The N—H···S hydrogen bonding interactions are quite often found in proteins, where the sulfur atoms are ususally from cysteine or methionine residues. Many organic compounds containing amide and thiol (or thioether) moieties were investigated to give a deep insight of the N—H···S hydrogen bonding interactions (Du et al. 2009), which may help to understand protein folding processes and enzymatic catalyses. Our group is interesting in the preparation and encapsulation behaviors of organic and inorganic supramolecules with dynamic covalent bonds (Huang et al. 2012; Wu et al. 2012). The title compound is a sulfur-containing secondary amide with two aryl groups. We synthesized and report its structure here, and will atempt to use it as a building block for the construction of more complex organic or inorganic molecules with unique properties.

The title compound crystallizes in the monoclinic space group P 21/c. Fig. 1. shows a displacement ellipsoid plot of the compound. The S—C(sp3) bond distane of 1.7876 (19) Å is slightly longer than those of the S—C(sp2) bonds [1.7678 (17) and 1.7708 (17) Å]. The two aromatic rings (C2 to C7) and (C9 to C14) exhibit a small interplanar angle of 16.03 (9) °. Both classical and non-classical hydrogen bonds are present (Table 1). The S atom with the Me group involves in an intramolecular hydrogen bond with the amido H-atom [N···S = 2.9150 (14) Å]. A non-classical intramolecular hydrogen bond of the type C—H···O also exists [C···O = 2.949 (2) Å]. In the crystal structure, the H atoms upon S atoms form intermolecular hydrogen bonds with the O atoms [S···O = 3.5976 (14) Å], connecting the compounds into zigzag chains along the c axis (Fig. 2).

For reversible organic and inorganic molecules with dynamic covalent bonds: see Huang et al. (2012); Wu et al. (2012). For aromatic amides with N—H···S interactions: see Du et al. (2009)

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids for the non-hydrogen atoms. The H atoms are dipicted by circles of an arbitrary radius.
[Figure 2] Fig. 2. A view of the one-dimensional zigzag hydrogen-bonded chain, displaying the hydrogen bonds as dashed lines.
N-[2-(Methylsulfanyl)phenyl]-2-sulfanylbenzamide top
Crystal data top
C14H13NOS2F(000) = 576
Mr = 275.37Dx = 1.424 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3996 reflections
a = 7.9549 (5) Åθ = 2.9–28.7°
b = 22.7530 (14) ŵ = 0.40 mm−1
c = 8.0966 (5) ÅT = 150 K
β = 118.787 (1)°Block, light-yellow
V = 1284.36 (14) Å30.49 × 0.12 × 0.08 mm
Z = 4
Data collection top
Bruker SMART APEXII
diffractometer		3196 independent reflections
Radiation source: fine-focus sealed tube2577 reflections with I > 2σ
Graphite monochromatorRint = 0.029
ω scansθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −10→10
Tmin = 0.828, Tmax = 0.969k = −30→29
14799 measured reflectionsl = −10→10
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0645P)2 + 0.2868P]
where P = (Fo2 + 2Fc2)/3
3196 reflections(Δ/σ)max = 0.011
172 parametersΔρmax = 0.54 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C14H13NOS2V = 1284.36 (14) Å3
Mr = 275.37Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.9549 (5) ŵ = 0.40 mm−1
b = 22.7530 (14) ÅT = 150 K
c = 8.0966 (5) Å0.49 × 0.12 × 0.08 mm
β = 118.787 (1)°
Data collection top
Bruker SMART APEXII
diffractometer		3196 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		2577 reflections with I > 2σ
Tmin = 0.828, Tmax = 0.969Rint = 0.029
14799 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.54 e Å−3
3196 reflectionsΔρmin = −0.24 e Å−3
172 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.60030 (6)−0.051148 (18)0.90758 (6)0.02864 (13)
S20.98708 (6)0.236365 (19)0.99798 (7)0.03244 (14)
C90.6995 (2)0.15183 (7)0.8772 (2)0.0221 (3)
C140.7592 (2)0.20651 (7)0.8423 (2)0.0238 (3)
C130.6343 (3)0.23749 (7)0.6799 (2)0.0280 (4)
H120.67330.27320.65380.034*
C70.9140 (2)0.01217 (7)1.1500 (2)0.0231 (3)
C100.5160 (2)0.13120 (7)0.7532 (2)0.0260 (3)
H90.47590.09530.77690.031*
C80.8306 (2)0.11675 (7)1.0481 (2)0.0229 (3)
C20.8275 (2)−0.04347 (7)1.1096 (2)0.0243 (3)
C110.3925 (2)0.16322 (8)0.5952 (3)0.0311 (4)
H100.26950.14940.51520.037*
C30.9226 (3)−0.09044 (8)1.2301 (3)0.0308 (4)
H40.8674−0.12761.20320.037*
C41.0979 (3)−0.08202 (8)1.3888 (3)0.0353 (4)
H51.1598−0.11341.46880.042*
C61.0906 (2)0.02020 (8)1.3094 (2)0.0294 (4)
H71.14800.05711.33610.035*
C120.4545 (3)0.21603 (8)0.5579 (3)0.0315 (4)
H110.37430.23710.44980.038*
C10.6034 (3)−0.12570 (8)0.8394 (3)0.0417 (5)
H30.7172−0.13250.82950.063*
H10.4924−0.13300.71980.063*
H20.6021−0.15160.93240.063*
C51.1817 (3)−0.02660 (9)1.4290 (3)0.0355 (4)
H61.2993−0.02091.53640.043*
N10.8202 (2)0.05779 (6)1.0186 (2)0.0234 (3)
O10.9345 (2)0.14000 (5)1.19986 (18)0.0374 (3)
H80.749 (3)0.0455 (9)0.910 (3)0.035 (6)*
H130.969 (4)0.2748 (11)0.881 (4)0.058 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0252 (2)0.0206 (2)0.0330 (2)0.00099 (15)0.00836 (18)−0.00087 (16)
S20.0276 (2)0.0233 (2)0.0391 (3)−0.00423 (16)0.01020 (19)0.00233 (17)
C90.0257 (8)0.0174 (7)0.0250 (8)0.0031 (6)0.0135 (7)0.0010 (6)
C140.0238 (7)0.0185 (8)0.0289 (8)0.0014 (6)0.0124 (7)−0.0001 (6)
C130.0325 (9)0.0212 (8)0.0328 (9)0.0051 (6)0.0178 (8)0.0057 (7)
C70.0254 (8)0.0208 (8)0.0237 (8)0.0040 (6)0.0123 (6)0.0023 (6)
C100.0274 (8)0.0194 (7)0.0307 (9)0.0003 (6)0.0136 (7)−0.0003 (6)
C80.0246 (8)0.0183 (7)0.0271 (8)0.0015 (6)0.0134 (7)0.0009 (6)
C20.0236 (8)0.0224 (8)0.0261 (8)0.0013 (6)0.0115 (7)0.0009 (6)
C110.0254 (8)0.0282 (9)0.0321 (9)0.0028 (7)0.0078 (7)−0.0024 (7)
C30.0328 (9)0.0237 (8)0.0348 (9)0.0012 (7)0.0154 (8)0.0057 (7)
C40.0363 (10)0.0322 (10)0.0315 (10)0.0089 (7)0.0117 (8)0.0101 (7)
C60.0294 (9)0.0254 (8)0.0289 (9)−0.0015 (7)0.0105 (7)−0.0030 (7)
C120.0342 (9)0.0270 (8)0.0292 (9)0.0093 (7)0.0119 (8)0.0058 (7)
C10.0379 (11)0.0281 (9)0.0467 (12)−0.0012 (8)0.0106 (9)−0.0110 (8)
C50.0318 (9)0.0380 (10)0.0261 (9)0.0036 (8)0.0053 (7)0.0045 (7)
N10.0262 (7)0.0169 (6)0.0231 (7)0.0006 (5)0.0087 (6)0.0005 (5)
O10.0450 (8)0.0210 (6)0.0295 (7)0.0010 (5)0.0046 (6)−0.0030 (5)
Geometric parameters (Å, º) top
S1—C21.7678 (17)C8—N11.358 (2)
S1—C11.7876 (19)C2—C31.399 (2)
S2—C141.7708 (17)C11—C121.386 (3)
S2—H131.24 (3)C11—H100.9300
C9—C101.395 (2)C3—C41.381 (3)
C9—C141.408 (2)C3—H40.9300
C9—C81.500 (2)C4—C51.390 (3)
C14—C131.398 (2)C4—H50.9300
C13—C121.378 (3)C6—C51.386 (3)
C13—H120.9300C6—H70.9300
C7—C61.388 (2)C12—H110.9300
C7—C21.402 (2)C1—H30.9600
C7—N11.415 (2)C1—H10.9600
C10—C111.386 (2)C1—H20.9600
C10—H90.9300C5—H60.9300
C8—O11.222 (2)N1—H80.83 (2)
C2—S1—C1102.68 (9)C12—C11—H10120.4
C14—S2—H1391.3 (12)C4—C3—C2120.52 (17)
C10—C9—C14119.32 (15)C4—C3—H4119.7
C10—C9—C8120.43 (14)C2—C3—H4119.7
C14—C9—C8120.24 (14)C3—C4—C5119.96 (17)
C13—C14—C9118.60 (15)C3—C4—H5120.0
C13—C14—S2119.75 (13)C5—C4—H5120.0
C9—C14—S2121.64 (12)C5—C6—C7120.20 (17)
C12—C13—C14121.19 (16)C5—C6—H7119.9
C12—C13—H12119.4C7—C6—H7119.9
C14—C13—H12119.4C13—C12—C11120.40 (16)
C6—C7—C2119.94 (15)C13—C12—H11119.8
C6—C7—N1122.27 (15)C11—C12—H11119.8
C2—C7—N1117.70 (14)S1—C1—H3109.5
C11—C10—C9121.21 (16)S1—C1—H1109.5
C11—C10—H9119.4H3—C1—H1109.5
C9—C10—H9119.4S1—C1—H2109.5
O1—C8—N1123.96 (15)H3—C1—H2109.5
O1—C8—C9122.02 (14)H1—C1—H2109.5
N1—C8—C9114.01 (14)C6—C5—C4120.21 (17)
C3—C2—C7119.15 (16)C6—C5—H6119.9
C3—C2—S1122.59 (13)C4—C5—H6119.9
C7—C2—S1118.26 (12)C8—N1—C7128.83 (14)
C10—C11—C12119.22 (16)C8—N1—H8118.1 (15)
C10—C11—H10120.4C7—N1—H8113.1 (15)
C10—C9—C14—C13−2.2 (2)C1—S1—C2—C3−30.12 (18)
C8—C9—C14—C13178.94 (15)C1—S1—C2—C7150.33 (15)
C10—C9—C14—S2177.94 (13)C9—C10—C11—C121.5 (3)
C8—C9—C14—S2−0.9 (2)C7—C2—C3—C41.1 (3)
C9—C14—C13—C121.5 (3)S1—C2—C3—C4−178.41 (14)
S2—C14—C13—C12−178.68 (14)C2—C3—C4—C5−0.5 (3)
C14—C9—C10—C110.8 (3)C2—C7—C6—C5−0.1 (3)
C8—C9—C10—C11179.58 (15)N1—C7—C6—C5−176.62 (16)
C10—C9—C8—O1−140.86 (17)C14—C13—C12—C110.8 (3)
C14—C9—C8—O137.9 (2)C10—C11—C12—C13−2.3 (3)
C10—C9—C8—N138.2 (2)C7—C6—C5—C40.8 (3)
C14—C9—C8—N1−143.00 (15)C3—C4—C5—C6−0.5 (3)
C6—C7—C2—C3−0.9 (3)O1—C8—N1—C73.2 (3)
N1—C7—C2—C3175.84 (15)C9—C8—N1—C7−175.82 (15)
C6—C7—C2—S1178.70 (13)C6—C7—N1—C8−28.8 (3)
N1—C7—C2—S1−4.6 (2)C2—C7—N1—C8154.54 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H8···S10.83 (2)2.49 (2)2.9150 (14)112.7 (17)
S2—H13···O1i1.24 (3)2.37 (3)3.5976 (14)169.5 (17)
C6—H7···O10.932.422.949 (2)116
Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC14H13NOS2
Mr275.37
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)7.9549 (5), 22.7530 (14), 8.0966 (5)
β (°) 118.787 (1)
V (Å3)1284.36 (14)
Z4
Radiation typeMo Kα
µ (mm−1)0.40
Crystal size (mm)0.49 × 0.12 × 0.08
Data collection
DiffractometerBruker SMART APEXII
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.828, 0.969
No. of measured, independent and
observed (I > 2σ) reflections		14799, 3196, 2577
Rint0.029
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.108, 1.07
No. of reflections3196
No. of parameters172
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.54, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H8···S10.83 (2)2.49 (2)2.9150 (14)112.7 (17)
S2—H13···O1i1.24 (3)2.37 (3)3.5976 (14)169.5 (17)
C6—H7···O10.932.422.949 (2)116.1
Symmetry code: (i) x, −y+1/2, z−1/2.
 

Acknowledgements

We thank the National Science Council of Taiwan for financial support of this work.

References

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ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2400
https://doi.org/10.1107/S1600536812029765
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