2-(Phenyl­sulfanyl)­aniline

Mdluli, V.; Golen, J.A.; Manke, D.R.

doi:10.1107/S241431461502489X

organic compounds

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ISSN: 2414-3146

Volume 1| Part 1| January 2016| x152489

doi:10.1107/S241431461502489X

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2-(Phenylsulfanyl)aniline

Velabo Mdluli,^a James A. Golen ^a and David R. Manke ^a ^*

^aDepartment of Chemistry and Biochemistry, University of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA
^*Correspondence e-mail: dmanke@umassd.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 25 December 2015; accepted 29 December 2015; online 16 January 2016)

In the title compound, C₁₂H₁₁NS, the aniline and phenyl rings have a skewed conformation with a dihedral angle of 81.31 (7)°. There is a short intramolecular N–H⋯S contact enclosing an S(5) ring motif. In the crystal, molecules are linked via N–H⋯S hydrogen bonds, forming chains along [10-3]. The chains are linked via N—H⋯π and C—H⋯π interactions, forming layers parallel to plane (010). No π–π interactions are noted between the layers.

Keywords: crystal structure; anilines; 2-arylthioanilines; hydrogen bonding.

CCDC reference: 1444623

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Chemical scheme

Structure description

2-(Arylsulfanyl)anilines have potential as pharmaceuticals, and herein we report the crystal structure of the parent 2-(phenylsulfanyl)aniline. In the title compound, Fig. 1, the aniline and phenyl rings have a skewed conformation with a dihedral angle of 81.31 (7)° and the C2—S1—C7 angle is 105.42 (10)°. This varies slightly from the values for 2-(p-tolylsulfanyl)aniline, where the corresponding dihedral angle is 87.80 (7)° and the C—S—C angle is 103.21 (12)° (Betz et al., 2011 ). There is a short intramolecular N1—H1B⋯S1 contact forming an S(5) ring motif (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯S1	0.86 (1)	2.61 (3)	3.054 (2)	113 (2)
N1—H1A⋯S1ⁱ	0.86 (1)	2.73 (1)	3.580 (2)	174 (2)
N1—H1B⋯Cg1ⁱⁱ	0.86 (1)	2.87 (3)	3.510 (2)	132 (2)
C6—H6⋯Cg2ⁱ	0.95	2.72	3.506 (2)	141
C9—H9⋯Cg1ⁱⁱⁱ	0.95	2.90	3.606 (2)	132
Symmetry codes: (i) $[x-{\script{1\over 4}}, -y+{\script{5\over 4}}, z+{\script{3\over 4}}]$ ; (ii) $[x-{\script{1\over 4}}, -y+{\script{5\over 4}}, z-{\script{1\over 4}}]$ ; (iii) $[x+{\script{1\over 4}}, -y+{\script{5\over 4}}, z+{\script{1\over 4}}]$ .

Figure 1
Molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The short intramolecular N—H⋯S contact is shown as a dashed line (see Table 1

In the crystal, molecules are linked via N1—H1A⋯S1 hydrogen bonds, forming chains along [10 $[\overline{3}]$ ]. The chains are linked by N—H⋯π and C—H⋯π interactions, forming layers that lie parallel to plane (010); Table 1 and Fig. 2. No π–π interactions are noted between the layers.

Figure 2
A view along the c axis of the crystal packing of the title compound, with hydrogen bonds shown as dashed lines (see Table 1

Though other 2-arylsulfanylanilines demonstrate intramolecular N—H⋯S hydrogen bonding, the observed intermolecular interactions are N—H⋯N hydrogen bonds (Yao et al., 2012 ; Beppu et al., 2014 ; Sellmann et al., 1999 ; Yuan et al., 2008 ). The structure of 2-[(4-methylphenyl)sulfanyl]aniline has been reported (Betz et al., 2011), as has that of another 2-arylthioaniline, 2-[(4-bromophenyl)sulfanyl]-4-nitroaniline (Yao et al., 2012).

Synthesis and crystallization

A commercial sample (Tokyo Chemical Industries) of the title compound was used for crystallization. Single crystals suitable for X-ray diffraction studies were grown by slow evaporation of a hexanes solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₁₁NS
M_r	201.28
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	120
a, b, c (Å)	17.7430 (7), 37.3075 (19), 6.1420 (2)
V (Å³)	4065.7 (3)
Z	16
Radiation type	Mo Kα
μ (mm⁻¹)	0.27
Crystal size (mm)	0.4 × 0.2 × 0.2

Data collection
Diffractometer	Bruker D8 Venture CMOS diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.717, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	14523, 1862, 1776
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.055, 1.10
No. of reflections	1862
No. of parameters	134
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16
Absolute structure	Flack x determined using 779 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.04 (3)
Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2014), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ), OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1444623

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S241431461502489X/su4007sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S241431461502489X/su4007Isup2.hkl

checkCIF report

Experimental top

Structure description top

2-(Arylsulfanyl)anilines have potential as pharmaceuticals, and herein we report the crystal structure of the parent 2-(phenylsulfanyl)aniline. In the title compound, Fig. 1, the aniline and phenyl rings have a skewed conformation with a dihedral angle of 81.31 (7)° and the C2—S1—C7 angle is 105.42 (10)°. This varies slightly from the values for 2-(p-tolylsulfanyl)aniline, where the corresponding dihedral angle is 87.80 (7)° and the C–S–C angle is 103.21 (12)° (Betz et al., 2011). There is a short intramolecular N1—H1B···S1 contact forming an S(5) ring motif (Table 1).

In the crystal, molecules are linked via N1—H1A···S1 hydrogen bonds, forming chains along [103]. The chains are linked by N—H···π and C—H···π interactions, forming layers that lie parallel to plane (010); Table 1 and Fig. 2. No π–π interactions are noted between the layers.

Though other 2-arylsulfanylanilines demonstrate intramolecular N—H···S hydrogen bonding, the observed intermolecular interactions are N—H···N hydrogen bonds (Yao et al., 2012; Beppu et al., 2014; Sellmann et al., 1999; Yuan et al., 2008). The structure of 2-[(4-methylphenyl)sulfanyl]aniline has been reported (Betz et al., 2011), as has that of another 2-arylsulfanylaniline, 2-[(4-bromophenyl)sulfanyl]-4-nitroaniline (Yao et al., 2012).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The short intramolecular N—H···S contact is shown as a dashed line (see Table 1).
	Fig. 2. A view along the c axis of the crystal packing of the title compound, with hydrogen bonds shown as dashed lines (see Table 1).

2-(Phenylsulfanyl)aniline top

Crystal data top

C₁₂H₁₁NS	F(000) = 1696
M_r = 201.28	D_x = 1.315 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 7209 reflections
a = 17.7430 (7) Å	θ = 3.2–25.3°
b = 37.3075 (19) Å	µ = 0.27 mm⁻¹
c = 6.1420 (2) Å	T = 120 K
V = 4065.7 (3) Å³	Block, colourless
Z = 16	0.4 × 0.2 × 0.2 mm

Data collection top

Bruker D8 Venture CMOS diffractometer	1862 independent reflections
Radiation source: fine-focus sealed tube	1776 reflections with I > 2σ(I)
TRIUMPH monochromator	R_int = 0.043
φ and ω scans	θ_max = 25.4°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −21→21
T_min = 0.717, T_max = 0.745	k = −44→44
14523 measured reflections	l = −7→7

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.055	w = 1/[σ²(F_o²) + (0.0293P)² + 1.8762P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
1862 reflections	Δρ_max = 0.15 e Å⁻³
134 parameters	Δρ_min = −0.16 e Å⁻³
3 restraints	Absolute structure: Flack x determined using 779 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (3)

Crystal data top

C₁₂H₁₁NS	V = 4065.7 (3) Å³
M_r = 201.28	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 17.7430 (7) Å	µ = 0.27 mm⁻¹
b = 37.3075 (19) Å	T = 120 K
c = 6.1420 (2) Å	0.4 × 0.2 × 0.2 mm

Data collection top

Bruker D8 Venture CMOS diffractometer	1862 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	1776 reflections with I > 2σ(I)
T_min = 0.717, T_max = 0.745	R_int = 0.043
14523 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.055	Δρ_max = 0.15 e Å⁻³
S = 1.10	Δρ_min = −0.16 e Å⁻³
1862 reflections	Absolute structure: Flack x determined using 779 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
134 parameters	Absolute structure parameter: 0.04 (3)
3 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.24353 (3)	0.61620 (2)	0.24971 (10)	0.01900 (14)
N1	0.15876 (11)	0.61631 (5)	0.6825 (3)	0.0238 (4)
C1	0.20904 (11)	0.64429 (6)	0.6541 (4)	0.0175 (5)
C2	0.25623 (10)	0.64606 (5)	0.4712 (3)	0.0169 (5)
C3	0.30828 (12)	0.67388 (5)	0.4495 (4)	0.0206 (5)
H3	0.3399	0.6748	0.3249	0.025*
C4	0.31437 (13)	0.70019 (6)	0.6072 (4)	0.0256 (5)
H4	0.3500	0.7191	0.5920	0.031*
C5	0.26753 (13)	0.69856 (6)	0.7883 (4)	0.0245 (5)
H5	0.2711	0.7165	0.8973	0.029*
C6	0.21570 (12)	0.67112 (6)	0.8121 (4)	0.0209 (5)
H6	0.1843	0.6705	0.9373	0.025*
C7	0.28473 (12)	0.57490 (6)	0.3348 (4)	0.0171 (5)
C8	0.32540 (11)	0.57064 (5)	0.5250 (4)	0.0194 (5)
H8	0.3286	0.5897	0.6272	0.023*
C9	0.36152 (12)	0.53829 (6)	0.5658 (4)	0.0239 (5)
H9	0.3902	0.5354	0.6953	0.029*
C10	0.35599 (13)	0.51019 (6)	0.4184 (4)	0.0267 (5)
H10	0.3815	0.4883	0.4457	0.032*
C11	0.31329 (12)	0.51427 (6)	0.2318 (4)	0.0271 (5)
H11	0.3082	0.4948	0.1331	0.033*
C12	0.27773 (13)	0.54671 (6)	0.1877 (4)	0.0230 (5)
H12	0.2489	0.5496	0.0585	0.028*
H1A	0.1217 (10)	0.6211 (6)	0.767 (4)	0.028*
H1B	0.1497 (15)	0.6036 (6)	0.568 (3)	0.037 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0204 (2)	0.0204 (2)	0.0162 (2)	0.0016 (2)	−0.0004 (2)	0.0009 (2)
N1	0.0230 (10)	0.0262 (10)	0.0222 (11)	−0.0040 (8)	0.0085 (8)	−0.0004 (9)
C1	0.0157 (10)	0.0181 (10)	0.0186 (11)	0.0045 (8)	−0.0003 (9)	0.0051 (9)
C2	0.0149 (9)	0.0161 (10)	0.0198 (12)	0.0032 (7)	−0.0016 (9)	0.0007 (9)
C3	0.0181 (10)	0.0205 (10)	0.0233 (12)	0.0007 (8)	0.0027 (9)	0.0052 (10)
C4	0.0252 (12)	0.0176 (11)	0.0339 (14)	−0.0032 (9)	−0.0025 (11)	0.0027 (10)
C5	0.0324 (12)	0.0167 (10)	0.0245 (15)	0.0062 (9)	−0.0057 (10)	−0.0030 (10)
C6	0.0196 (10)	0.0245 (12)	0.0187 (11)	0.0084 (9)	0.0006 (9)	0.0023 (9)
C7	0.0144 (10)	0.0158 (11)	0.0212 (11)	−0.0020 (8)	0.0037 (9)	−0.0009 (9)
C8	0.0213 (10)	0.0172 (10)	0.0197 (11)	−0.0036 (8)	0.0006 (10)	−0.0005 (9)
C9	0.0244 (11)	0.0241 (11)	0.0233 (12)	−0.0007 (9)	−0.0001 (10)	0.0034 (10)
C10	0.0285 (12)	0.0176 (11)	0.0339 (14)	0.0021 (9)	0.0063 (11)	0.0032 (10)
C11	0.0300 (11)	0.0196 (11)	0.0318 (14)	−0.0033 (9)	0.0069 (11)	−0.0088 (11)
C12	0.0215 (11)	0.0275 (12)	0.0202 (12)	−0.0029 (9)	0.0005 (9)	−0.0031 (9)

Geometric parameters (Å, º) top

S1—C2	1.772 (2)	C5—C6	1.384 (3)
S1—C7	1.784 (2)	C6—H6	0.9500
N1—C1	1.384 (3)	C7—C8	1.383 (3)
N1—H1A	0.857 (7)	C7—C12	1.392 (3)
N1—H1B	0.862 (7)	C8—H8	0.9500
C1—C2	1.403 (3)	C8—C9	1.389 (3)
C1—C6	1.400 (3)	C9—H9	0.9500
C2—C3	1.396 (3)	C9—C10	1.388 (3)
C3—H3	0.9500	C10—H10	0.9500
C3—C4	1.383 (3)	C10—C11	1.382 (4)
C4—H4	0.9500	C11—H11	0.9500
C4—C5	1.390 (3)	C11—C12	1.391 (3)
C5—H5	0.9500	C12—H12	0.9500

C2—S1—C7	105.42 (10)	C5—C6—C1	120.8 (2)
C1—N1—H1A	114.4 (16)	C5—C6—H6	119.6
C1—N1—H1B	115.7 (19)	C8—C7—S1	124.12 (17)
H1A—N1—H1B	118 (3)	C8—C7—C12	120.5 (2)
N1—C1—C2	121.4 (2)	C12—C7—S1	115.22 (17)
N1—C1—C6	120.4 (2)	C7—C8—H8	120.2
C6—C1—C2	118.13 (19)	C7—C8—C9	119.5 (2)
C1—C2—S1	120.60 (16)	C9—C8—H8	120.2
C3—C2—S1	118.58 (16)	C8—C9—H9	119.8
C3—C2—C1	120.4 (2)	C10—C9—C8	120.4 (2)
C2—C3—H3	119.6	C10—C9—H9	119.8
C4—C3—C2	120.8 (2)	C9—C10—H10	120.1
C4—C3—H3	119.6	C11—C10—C9	119.7 (2)
C3—C4—H4	120.6	C11—C10—H10	120.1
C3—C4—C5	118.9 (2)	C10—C11—H11	119.8
C5—C4—H4	120.6	C10—C11—C12	120.4 (2)
C4—C5—H5	119.5	C12—C11—H11	119.8
C6—C5—C4	121.0 (2)	C7—C12—H12	120.3
C6—C5—H5	119.5	C11—C12—C7	119.4 (2)
C1—C6—H6	119.6	C11—C12—H12	120.3

S1—C2—C3—C4	172.78 (17)	C4—C5—C6—C1	−0.1 (3)
S1—C7—C8—C9	−173.59 (16)	C6—C1—C2—S1	−172.52 (16)
S1—C7—C12—C11	174.84 (17)	C6—C1—C2—C3	0.1 (3)
N1—C1—C2—S1	9.5 (3)	C7—S1—C2—C1	−78.46 (18)
N1—C1—C2—C3	−177.8 (2)	C7—S1—C2—C3	108.74 (16)
N1—C1—C6—C5	177.9 (2)	C7—C8—C9—C10	−1.0 (3)
C1—C2—C3—C4	0.0 (3)	C8—C7—C12—C11	−1.2 (3)
C2—S1—C7—C8	−7.2 (2)	C8—C9—C10—C11	−1.1 (3)
C2—S1—C7—C12	176.93 (16)	C9—C10—C11—C12	1.9 (3)
C2—C1—C6—C5	−0.1 (3)	C10—C11—C12—C7	−0.8 (3)
C2—C3—C4—C5	−0.1 (3)	C12—C7—C8—C9	2.1 (3)
C3—C4—C5—C6	0.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···S1	0.86 (1)	2.61 (3)	3.054 (2)	113 (2)
N1—H1A···S1ⁱ	0.86 (1)	2.73 (1)	3.580 (2)	174 (2)
N1—H1B···Cg1ⁱⁱ	0.86 (1)	2.87 (3)	3.510 (2)	132 (2)
C6—H6···Cg2ⁱ	0.95	2.72	3.506 (2)	141
C9—H9···Cg1ⁱⁱⁱ	0.95	2.90	3.606 (2)	132

Symmetry codes: (i) x−1/4, −y+5/4, z+3/4; (ii) x−1/4, −y+5/4, z−1/4; (iii) x+1/4, −y+5/4, z+1/4.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···S1	0.86 (1)	2.61 (3)	3.054 (2)	113 (2)
N1—H1A···S1ⁱ	0.86 (1)	2.727 (8)	3.580 (2)	174 (2)
N1—H1B···Cg1ⁱⁱ	0.862 (7)	2.87 (3)	3.510 (2)	132 (2)
C6—H6···Cg2ⁱ	0.95	2.72	3.506 (2)	141
C9—H9···Cg1ⁱⁱⁱ	0.95	2.90	3.606 (2)	132

Symmetry codes: (i) x−1/4, −y+5/4, z+3/4; (ii) x−1/4, −y+5/4, z−1/4; (iii) x+1/4, −y+5/4, z+1/4.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁NS
M_r	201.28
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	120
a, b, c (Å)	17.7430 (7), 37.3075 (19), 6.1420 (2)
V (Å³)	4065.7 (3)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.4 × 0.2 × 0.2

Data collection
Diffractometer	Bruker D8 Venture CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2014)
T_min, T_max	0.717, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	14523, 1862, 1776
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.055, 1.10
No. of reflections	1862
No. of parameters	134
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16
Absolute structure	Flack x determined using 779 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Absolute structure parameter	0.04 (3)

Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2014), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), OLEX2 (Dolomanov et al., 2009), OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

Acknowledgements

Support from the National Science Foundation (CHE-1429086) is gratefully acknowledge.

References

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ISSN: 2414-3146

Volume 1| Part 1| January 2016| x152489

doi:10.1107/S241431461502489X

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

2-(Phenyl­sulfanyl)­aniline

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

2-(Phenylsulfanyl)aniline