2,4-Disulfanyl-6-[(E)-(2-sulfanylbenz­yl)imino­meth­yl]phenol

Cui, Y.-M.; Dai, X.-B.; Lei, L.; Zeng, Q.-F.

doi:10.1107/S160053680903205X

organic compounds

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Volume 65| Part 9| September 2009| Page o2179

doi:10.1107/S160053680903205X

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2,4-Disulfanyl-6-[(E)-(2-sulfanylbenzyl)iminomethyl]phenol

Yong-Ming Cui,^a Xi-Bin Dai,^a Lei Lei ^a and Qing-Fu Zeng ^a ^*

^aEngineering Research Center for Clean Production of Textile Dyeing and Printing, Ministry of Education, Wuhan 430073, People's Republic of China
^*Correspondence e-mail: qfzeng@wuse.edu.cn

(Received 12 August 2009; accepted 13 August 2009; online 19 August 2009)

In the title compound, C₁₄H₁₃NOS₃, the dihedral angle between the benzene rings is 73.26 (5)° and an intramolecular O—H⋯N hydrogen bond occurs.

Related literature

For background, see: Shi et al. (2007 ). For reference structural data, see: Allen et al. (1987 );

Experimental

Crystal data

C₁₄H₁₃NOS₃
M_r = 307.43
Monoclinic, P 2₁ /c
a = 11.9763 (13) Å
b = 8.2333 (13) Å
c = 14.2213 (13) Å
β = 98.723 (3)°
V = 1386.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 296 K
0.28 × 0.25 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.867, T_max = 0.880
7137 measured reflections
2443 independent reflections
1929 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.140
S = 1.06
2443 reflections
176 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.591 (3)	147

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903205X/hb5045sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903205X/hb5045Isup2.hkl

checkCIF report

Comment top

There has been much research interest in Schiff base compounds due to their biological activities (Shi et al., 2007). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). There ais an intramolecular O—H···N hydrogen bond (Table 1) in (I). The dihedral angle between the two benzene rings is 73.26 (0.05) °.

Related literature top

For background, see: Shi et al. (2007). For reference structural data, see: Allen et al. (1987);

Experimental top

A mixture of 2-hydroxy-3,5-disulfanylbenzaldehyde (186 mg, 1 mmol) and 2-(aminomethyl)benzenethiol (139 mg, 1 mmol) in methanol (10 ml) was stirred for 2 h. After keeping the filtrate in air for 6 d, yellow blocks of (I) were formed.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids.

2,4-Disulfanyl-6-[(E)-(2-sulfanylbenzyl)iminomethyl]phenol top

Crystal data top

C₁₄H₁₃NOS₃	F(000) = 640
M_r = 307.43	D_x = 1.473 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.9763 (13) Å	θ = 9–12°
b = 8.2333 (13) Å	µ = 0.52 mm⁻¹
c = 14.2213 (13) Å	T = 296 K
β = 98.723 (3)°	Block, yellow
V = 1386.1 (3) Å³	0.28 × 0.25 × 0.25 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2443 independent reflections
Radiation source: fine-focus sealed tube	1929 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω/2θ scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: ψ scan (North et al., 1968)	h = −14→10
T_min = 0.867, T_max = 0.880	k = −9→9
7137 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0746P)² + 0.5508P] where P = (F_o² + 2F_c²)/3
2443 reflections	(Δ/σ)_max = 0.002
176 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₄H₁₃NOS₃	V = 1386.1 (3) Å³
M_r = 307.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9763 (13) Å	µ = 0.52 mm⁻¹
b = 8.2333 (13) Å	T = 296 K
c = 14.2213 (13) Å	0.28 × 0.25 × 0.25 mm
β = 98.723 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2443 independent reflections
Absorption correction: ψ scan (North et al., 1968)	1929 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.880	R_int = 0.025
7137 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.06	Δρ_max = 0.28 e Å⁻³
2443 reflections	Δρ_min = −0.39 e Å⁻³
176 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

	x	y	z	U_iso*/U_eq
C2	0.3001 (2)	0.0386 (3)	−0.0207 (2)	0.0502 (6)
H2	0.2415	−0.0310	−0.0118	0.060*
C3	0.3723 (2)	0.0988 (3)	0.05602 (18)	0.0468 (6)
C4	0.46151 (19)	0.2023 (3)	0.04542 (18)	0.0441 (6)
C5	0.4777 (2)	0.2435 (3)	−0.04744 (18)	0.0448 (6)
C6	0.4044 (2)	0.1839 (3)	−0.1250 (2)	0.0532 (7)
H6	0.4148	0.2118	−0.1864	0.064*
C7	0.3166 (2)	0.0837 (3)	−0.1110 (2)	0.0538 (7)
C8	0.9011 (2)	0.3750 (3)	0.1048 (2)	0.0551 (7)
C9	0.8496 (2)	0.3907 (3)	0.0113 (2)	0.0478 (6)
C10	0.7427 (2)	0.4868 (3)	−0.0169 (3)	0.0605 (8)
H10A	0.7476	0.5890	0.0174	0.073*
H10B	0.7333	0.5106	−0.0844	0.073*
C11	0.8989 (2)	0.3091 (3)	−0.0574 (2)	0.0594 (7)
H11	0.8660	0.3151	−0.1209	0.071*
C12	0.9966 (3)	0.2189 (4)	−0.0324 (3)	0.0718 (9)
H12	1.0297	0.1668	−0.0792	0.086*
C13	1.0442 (3)	0.2064 (4)	0.0608 (3)	0.0726 (9)
H13	1.1092	0.1445	0.0772	0.087*
C14	0.9971 (3)	0.2840 (4)	0.1300 (2)	0.0690 (8)
H14	1.0297	0.2753	0.1934	0.083*
C15	0.5736 (2)	0.3436 (3)	−0.0638 (2)	0.0523 (7)
H15	0.5821	0.3710	−0.1257	0.063*
N1	0.64557 (17)	0.3939 (3)	0.00480 (18)	0.0541 (6)
O1	0.52860 (16)	0.2588 (2)	0.12252 (13)	0.0597 (5)
H1	0.5820	0.3078	0.1060	0.090*
S1	0.35256 (7)	0.04078 (11)	0.16895 (5)	0.0677 (3)
H1A	0.4408	−0.0037	0.2128	0.102*
S2	0.22437 (8)	0.01029 (13)	−0.20692 (7)	0.0860 (4)
H2A	0.2734	−0.0823	−0.2515	0.129*
S3	0.84366 (10)	0.47293 (14)	0.19417 (7)	0.0939 (4)
H3A	0.8005	0.5977	0.1640	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0407 (14)	0.0441 (14)	0.0657 (18)	0.0040 (11)	0.0080 (12)	−0.0050 (12)
C3	0.0450 (14)	0.0445 (14)	0.0537 (15)	0.0098 (11)	0.0161 (11)	−0.0037 (11)
C4	0.0379 (13)	0.0410 (13)	0.0531 (15)	0.0074 (10)	0.0060 (11)	−0.0070 (11)
C5	0.0394 (13)	0.0392 (13)	0.0555 (15)	0.0099 (10)	0.0059 (11)	0.0044 (11)
C6	0.0543 (16)	0.0523 (15)	0.0514 (15)	0.0073 (12)	0.0029 (12)	0.0093 (12)
C7	0.0475 (15)	0.0527 (15)	0.0575 (17)	0.0041 (12)	−0.0037 (12)	−0.0010 (13)
C8	0.0483 (15)	0.0544 (16)	0.0643 (18)	−0.0054 (13)	0.0144 (13)	−0.0064 (13)
C9	0.0399 (13)	0.0369 (13)	0.0683 (17)	−0.0032 (10)	0.0136 (12)	0.0039 (11)
C10	0.0440 (15)	0.0444 (15)	0.095 (2)	0.0030 (11)	0.0151 (14)	0.0117 (14)
C11	0.0616 (17)	0.0542 (16)	0.0662 (18)	0.0002 (13)	0.0223 (14)	0.0053 (13)
C12	0.072 (2)	0.0588 (18)	0.094 (2)	0.0109 (15)	0.0409 (19)	−0.0026 (17)
C13	0.0478 (17)	0.067 (2)	0.105 (3)	0.0124 (15)	0.0171 (17)	0.0114 (19)
C14	0.0527 (17)	0.076 (2)	0.075 (2)	−0.0016 (15)	−0.0010 (15)	0.0072 (17)
C15	0.0477 (15)	0.0453 (14)	0.0651 (17)	0.0099 (12)	0.0121 (13)	0.0103 (12)
N1	0.0395 (12)	0.0460 (12)	0.0771 (16)	0.0029 (9)	0.0100 (11)	0.0029 (11)
O1	0.0542 (11)	0.0678 (13)	0.0566 (11)	−0.0068 (9)	0.0063 (9)	−0.0133 (9)
S1	0.0733 (5)	0.0826 (6)	0.0530 (5)	−0.0086 (4)	0.0280 (4)	−0.0057 (4)
S2	0.0784 (6)	0.1025 (7)	0.0678 (6)	−0.0198 (5)	−0.0192 (4)	−0.0078 (5)
S3	0.1002 (8)	0.1088 (8)	0.0779 (6)	0.0057 (6)	0.0300 (5)	−0.0335 (5)

Geometric parameters (Å, º) top

C2—C3	1.377 (4)	C10—N1	1.464 (3)
C2—C7	1.380 (4)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C3—C4	1.392 (4)	C11—C12	1.386 (4)
C3—S1	1.726 (3)	C11—H11	0.9300
C4—O1	1.341 (3)	C12—C13	1.364 (5)
C4—C5	1.405 (4)	C12—H12	0.9300
C5—C6	1.391 (4)	C13—C14	1.365 (5)
C5—C15	1.461 (4)	C13—H13	0.9300
C6—C7	1.374 (4)	C14—H14	0.9300
C6—H6	0.9300	C15—N1	1.269 (3)
C7—S2	1.729 (3)	C15—H15	0.9300
C8—C14	1.374 (4)	O1—H1	0.8200
C8—C9	1.384 (4)	S1—H1A	1.2000
C8—S3	1.733 (3)	S2—H2A	1.2000
C9—C11	1.390 (4)	S3—H3A	1.2000
C9—C10	1.507 (4)

C3—C2—C7	118.7 (2)	N1—C10—H10A	109.7
C3—C2—H2	120.7	C9—C10—H10A	109.7
C7—C2—H2	120.7	N1—C10—H10B	109.7
C2—C3—C4	122.3 (2)	C9—C10—H10B	109.7
C2—C3—S1	118.6 (2)	H10A—C10—H10B	108.2
C4—C3—S1	119.1 (2)	C12—C11—C9	120.7 (3)
O1—C4—C3	119.9 (2)	C12—C11—H11	119.7
O1—C4—C5	122.3 (2)	C9—C11—H11	119.7
C3—C4—C5	117.9 (2)	C13—C12—C11	120.1 (3)
C6—C5—C4	119.9 (2)	C13—C12—H12	119.9
C6—C5—C15	119.4 (2)	C11—C12—H12	119.9
C4—C5—C15	120.7 (2)	C12—C13—C14	120.5 (3)
C7—C6—C5	120.2 (3)	C12—C13—H13	119.7
C7—C6—H6	119.9	C14—C13—H13	119.7
C5—C6—H6	119.9	C13—C14—C8	119.3 (3)
C6—C7—C2	121.1 (2)	C13—C14—H14	120.4
C6—C7—S2	120.5 (2)	C8—C14—H14	120.4
C2—C7—S2	118.4 (2)	N1—C15—C5	121.4 (3)
C14—C8—C9	122.3 (3)	N1—C15—H15	119.3
C14—C8—S3	118.2 (2)	C5—C15—H15	119.3
C9—C8—S3	119.5 (2)	C15—N1—C10	118.5 (3)
C8—C9—C11	117.1 (2)	C4—O1—H1	109.5
C8—C9—C10	122.8 (3)	C3—S1—H1A	109.5
C11—C9—C10	120.0 (3)	C7—S2—H2A	109.5
N1—C10—C9	109.9 (2)	C8—S3—H3A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.591 (3)	147

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NOS₃
M_r	307.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.9763 (13), 8.2333 (13), 14.2213 (13)
β (°)	98.723 (3)
V (Å³)	1386.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.28 × 0.25 × 0.25

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.867, 0.880
No. of measured, independent and observed [I > 2σ(I)] reflections	7137, 2443, 1929
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.140, 1.06
No. of reflections	2443
No. of parameters	176
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.39

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.591 (3)	147

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, L., Ge, H.-M., Tan, S.-H., Li, H.-Q., Song, Y.-C., Zhu, H.-L. & Tan, R.-X. (2007). Eur. J. Med. Chem. 42, 558–564. Web of Science CrossRef PubMed CAS Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2179

doi:10.1107/S160053680903205X

Open

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