2,4-Disulfanyl-6-[(E)-(2-sulfanylbenz-yl)imino-meth-yl]phenol.

In the title compound, C(14)H(13)NOS(3), the dihedral angle between the benzene rings is 73.26 (5)° and an intra-molecular 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 = 307.43

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.140

S = 1.06

2443 reflections

176 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.39 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H13NOS3	F(000) = 640
Mr = 307.43	Dx = 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

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

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(Fo2) + (0.0746P)2 + 0.5508P] where P = (Fo2 + 2Fc2)/3
2443 reflections	(Δ/σ)max = 0.002
176 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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
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*

	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)

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

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

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