5-[(E)-(2-Hy-droxy-benzyl-idene)amino]-1H-1,3-benzimidazole-2(3H)-thione.

There are two mol-ecules in the asymmetric unit of the title compound, C(14)H(11)N(3)OS. In each, the benzimidazole ring system is essentially planar, with maximum deviations of 0.010 (2) and 0.006 (2) Å, and makes dihedral angles of 8.70 (9) and 13.75 (8)°, respectively, with the hy-droxy-substituted benzene rings. Each mol-ecule adopts an E configuration about the central C=N double bond. In the crystal, the two independent mol-ecules are connected via inter-molecular N-H⋯S hydrogen bonds, forming dimers. Furthermore, the dimers are connected by N-H⋯O hydrogen bonds into mol-ecular ribbons along the c axis. There is an intra-molecular O-H⋯N hydrogen bond in each mol-ecule, which generates an S(6) ring motif.

Related literature

For applications of benzimidazole compounds, see: Grassmann et al. (2002 ▶); White et al. (2004 ▶); Demirayak et al. (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H11N3OS

M = 269.32

Monoclinic,

a = 8.2680 (2) Å

b = 28.1043 (6) Å

c = 10.5047 (2) Å

β = 92.234 (1)°

V = 2439.08 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.44 × 0.28 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.894, T max = 0.986

27759 measured reflections

7101 independent reflections

4852 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.140

S = 1.06

7101 reflections

367 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681005172X/rz2535sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005172X/rz2535Isup2.hkl

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

C14H11N3OS	F(000) = 1120
Mr = 269.32	Dx = 1.467 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5349 reflections
a = 8.2680 (2) Å	θ = 2.4–29.8°
b = 28.1043 (6) Å	µ = 0.26 mm−1
c = 10.5047 (2) Å	T = 296 K
β = 92.234 (1)°	Plate, yellow
V = 2439.08 (9) Å3	0.44 × 0.28 × 0.05 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	7101 independent reflections
Radiation source: fine-focus sealed tube	4852 reflections with I > 2σ(I)
graphite	Rint = 0.064
φ and ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.894, Tmax = 0.986	k = −32→39
27759 measured reflections	l = −14→13

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.8644P] where P = (Fo2 + 2Fc2)/3
7101 reflections	(Δ/σ)max = 0.003
367 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1A	0.21140 (7)	1.12383 (2)	0.02847 (5)	0.02132 (14)
O1A	0.50964 (18)	0.77807 (6)	0.17652 (15)	0.0221 (4)
N1A	0.4066 (2)	1.05753 (7)	0.14802 (17)	0.0172 (4)
N2A	0.2149 (2)	1.02767 (7)	0.02468 (17)	0.0183 (4)
N3A	0.3807 (2)	0.86052 (7)	0.12424 (16)	0.0176 (4)
C1A	0.2805 (3)	1.06914 (8)	0.06700 (19)	0.0175 (4)
C2A	0.2993 (2)	0.98911 (8)	0.07630 (19)	0.0160 (4)
C3A	0.2787 (3)	0.94091 (8)	0.0614 (2)	0.0184 (5)
H3AA	0.1966	0.9286	0.0080	0.022*
C4A	0.3863 (2)	0.91097 (8)	0.12978 (19)	0.0166 (4)
C5A	0.5118 (2)	0.93050 (8)	0.2077 (2)	0.0189 (5)
H5AA	0.5835	0.9101	0.2509	0.023*
C6A	0.5317 (3)	0.97925 (8)	0.2220 (2)	0.0190 (5)
H6AA	0.6150	0.9918	0.2737	0.023*
C7A	0.4226 (2)	1.00835 (8)	0.15642 (19)	0.0167 (4)
C8A	0.2587 (2)	0.83866 (8)	0.07064 (19)	0.0178 (5)
H8AA	0.1735	0.8563	0.0349	0.021*
C9A	0.2517 (2)	0.78727 (8)	0.06494 (19)	0.0158 (4)
C10A	0.1181 (3)	0.76507 (8)	0.0031 (2)	0.0191 (5)
H10A	0.0374	0.7837	−0.0358	0.023*
C11A	0.1047 (3)	0.71658 (8)	−0.0008 (2)	0.0221 (5)
H11A	0.0167	0.7024	−0.0436	0.027*
C12A	0.2235 (3)	0.68861 (8)	0.0597 (2)	0.0219 (5)
H12A	0.2127	0.6557	0.0595	0.026*
C13A	0.3581 (3)	0.70934 (8)	0.1204 (2)	0.0204 (5)
H13A	0.4368	0.6904	0.1606	0.025*
C14A	0.3744 (2)	0.75836 (8)	0.12070 (19)	0.0170 (4)
S1B	0.70785 (7)	0.13290 (2)	0.26867 (5)	0.02190 (15)
O1B	0.57264 (18)	0.46335 (6)	0.28156 (14)	0.0200 (3)
N1B	0.6814 (2)	0.23011 (7)	0.26320 (16)	0.0162 (4)
N2B	0.4813 (2)	0.19309 (7)	0.16560 (17)	0.0164 (4)
N3B	0.4551 (2)	0.38927 (7)	0.17211 (16)	0.0169 (4)
C1B	0.6236 (3)	0.18613 (8)	0.23241 (19)	0.0173 (4)
C2B	0.5767 (2)	0.26526 (8)	0.21513 (18)	0.0146 (4)
C3B	0.5805 (2)	0.31452 (8)	0.22219 (19)	0.0166 (4)
H3BA	0.6648	0.3305	0.2649	0.020*
C4B	0.4516 (2)	0.33902 (8)	0.16207 (19)	0.0158 (4)
C5B	0.3242 (2)	0.31426 (8)	0.0986 (2)	0.0178 (5)
H5BA	0.2401	0.3314	0.0592	0.021*
C6B	0.3211 (2)	0.26541 (8)	0.09358 (19)	0.0180 (5)
H6BA	0.2364	0.2492	0.0518	0.022*
C7B	0.4495 (2)	0.24101 (8)	0.15326 (19)	0.0156 (4)
C8B	0.3622 (3)	0.41641 (8)	0.10194 (19)	0.0178 (4)
H8BA	0.2919	0.4027	0.0412	0.021*
C9B	0.3649 (2)	0.46731 (8)	0.11564 (19)	0.0172 (4)
C10B	0.2614 (3)	0.49637 (8)	0.0404 (2)	0.0213 (5)
H10B	0.1878	0.4822	−0.0171	0.026*
C11B	0.2659 (3)	0.54507 (9)	0.0494 (2)	0.0244 (5)
H11B	0.1962	0.5637	−0.0013	0.029*
C12B	0.3766 (3)	0.56628 (9)	0.1357 (2)	0.0238 (5)
H12B	0.3814	0.5993	0.1413	0.029*
C13B	0.4791 (3)	0.53897 (8)	0.2129 (2)	0.0204 (5)
H13B	0.5519	0.5536	0.2702	0.024*
C14B	0.4731 (2)	0.48965 (8)	0.20457 (19)	0.0162 (4)
H1NA	0.475 (4)	1.0777 (10)	0.181 (3)	0.043 (9)*
H2NA	0.145 (3)	1.0262 (9)	−0.038 (3)	0.033 (7)*
H1NB	0.774 (3)	0.2355 (9)	0.302 (2)	0.026 (7)*
H2NB	0.424 (3)	0.1704 (10)	0.139 (2)	0.031 (8)*
H1OB	0.548 (4)	0.4299 (13)	0.259 (3)	0.077 (12)*
H1OA	0.501 (4)	0.8131 (13)	0.168 (3)	0.075 (12)*

	U11	U22	U33	U12	U13	U23
S1A	0.0222 (3)	0.0178 (3)	0.0236 (3)	−0.0002 (2)	−0.0030 (2)	0.0006 (2)
O1A	0.0183 (8)	0.0214 (10)	0.0261 (8)	0.0010 (7)	−0.0065 (6)	−0.0010 (7)
N1A	0.0165 (8)	0.0158 (10)	0.0191 (9)	−0.0018 (7)	0.0002 (7)	−0.0006 (7)
N2A	0.0205 (9)	0.0166 (10)	0.0176 (9)	−0.0005 (8)	−0.0022 (7)	0.0003 (7)
N3A	0.0190 (9)	0.0185 (11)	0.0153 (8)	0.0003 (7)	0.0023 (7)	0.0005 (7)
C1A	0.0178 (10)	0.0195 (12)	0.0154 (9)	−0.0011 (9)	0.0035 (8)	−0.0015 (8)
C2A	0.0169 (10)	0.0176 (12)	0.0137 (9)	−0.0002 (8)	0.0025 (8)	0.0006 (8)
C3A	0.0169 (10)	0.0208 (13)	0.0173 (10)	−0.0014 (9)	−0.0007 (8)	−0.0001 (9)
C4A	0.0172 (10)	0.0169 (12)	0.0161 (10)	0.0002 (8)	0.0049 (8)	−0.0009 (8)
C5A	0.0158 (10)	0.0222 (13)	0.0185 (10)	0.0023 (9)	0.0003 (8)	0.0003 (9)
C6A	0.0161 (10)	0.0232 (13)	0.0177 (10)	−0.0006 (9)	−0.0001 (8)	−0.0007 (9)
C7A	0.0177 (10)	0.0162 (12)	0.0165 (9)	−0.0028 (8)	0.0037 (8)	−0.0007 (8)
C8A	0.0152 (9)	0.0225 (13)	0.0158 (10)	0.0029 (9)	0.0023 (8)	0.0012 (9)
C9A	0.0150 (10)	0.0178 (12)	0.0148 (9)	0.0013 (8)	0.0033 (8)	0.0011 (8)
C10A	0.0147 (9)	0.0202 (13)	0.0222 (11)	0.0007 (9)	0.0001 (8)	0.0008 (9)
C11A	0.0162 (10)	0.0242 (14)	0.0259 (11)	−0.0037 (9)	0.0006 (9)	−0.0013 (10)
C12A	0.0215 (11)	0.0163 (13)	0.0282 (12)	−0.0008 (9)	0.0042 (9)	0.0015 (9)
C13A	0.0182 (10)	0.0230 (13)	0.0200 (10)	0.0057 (9)	0.0002 (8)	0.0036 (9)
C14A	0.0157 (9)	0.0205 (12)	0.0149 (9)	−0.0010 (9)	0.0027 (8)	−0.0010 (8)
S1B	0.0239 (3)	0.0184 (3)	0.0230 (3)	0.0036 (2)	−0.0042 (2)	−0.0003 (2)
O1B	0.0208 (8)	0.0181 (9)	0.0208 (8)	−0.0001 (6)	−0.0044 (6)	0.0007 (6)
N1B	0.0153 (8)	0.0170 (10)	0.0162 (8)	0.0002 (7)	−0.0014 (7)	−0.0006 (7)
N2B	0.0165 (8)	0.0146 (10)	0.0180 (8)	−0.0011 (8)	0.0001 (7)	−0.0020 (7)
N3B	0.0171 (8)	0.0161 (10)	0.0176 (8)	0.0002 (7)	0.0028 (7)	−0.0003 (7)
C1B	0.0181 (10)	0.0197 (12)	0.0143 (9)	0.0007 (9)	0.0030 (8)	−0.0013 (8)
C2B	0.0135 (9)	0.0185 (12)	0.0118 (9)	0.0003 (8)	0.0019 (7)	−0.0009 (8)
C3B	0.0152 (9)	0.0198 (12)	0.0149 (9)	−0.0025 (8)	0.0010 (8)	−0.0026 (8)
C4B	0.0177 (10)	0.0150 (12)	0.0152 (9)	0.0005 (8)	0.0047 (8)	0.0001 (8)
C5B	0.0149 (9)	0.0189 (12)	0.0197 (10)	0.0011 (9)	0.0006 (8)	0.0016 (9)
C6B	0.0154 (10)	0.0202 (12)	0.0182 (10)	−0.0028 (8)	−0.0007 (8)	−0.0010 (9)
C7B	0.0162 (9)	0.0164 (12)	0.0142 (9)	−0.0007 (8)	0.0030 (8)	−0.0013 (8)
C8B	0.0200 (10)	0.0181 (12)	0.0154 (9)	−0.0016 (9)	0.0021 (8)	−0.0020 (8)
C9B	0.0187 (10)	0.0183 (12)	0.0148 (9)	−0.0006 (9)	0.0027 (8)	0.0000 (8)
C10B	0.0237 (11)	0.0217 (13)	0.0183 (10)	0.0011 (9)	−0.0016 (9)	0.0003 (9)
C11B	0.0299 (12)	0.0220 (14)	0.0213 (11)	0.0075 (10)	0.0003 (9)	0.0042 (9)
C12B	0.0313 (12)	0.0182 (13)	0.0221 (11)	0.0024 (10)	0.0053 (10)	0.0012 (9)
C13B	0.0219 (11)	0.0199 (13)	0.0194 (10)	−0.0016 (9)	0.0020 (9)	−0.0028 (9)
C14B	0.0164 (9)	0.0168 (12)	0.0156 (9)	0.0012 (8)	0.0044 (8)	0.0006 (8)

S1A—C1A	1.684 (2)	S1B—C1B	1.688 (2)
O1A—C14A	1.360 (2)	O1B—C14B	1.351 (2)
O1A—H1OA	0.99 (4)	O1B—H1OB	0.99 (4)
N1A—C1A	1.359 (3)	N1B—C1B	1.359 (3)
N1A—C7A	1.391 (3)	N1B—C2B	1.395 (3)
N1A—H1NA	0.86 (3)	N1B—H1NB	0.87 (2)
N2A—C1A	1.353 (3)	N2B—C1B	1.360 (3)
N2A—C2A	1.388 (3)	N2B—C7B	1.377 (3)
N2A—H2NA	0.86 (3)	N2B—H2NB	0.84 (3)
N3A—C8A	1.291 (3)	N3B—C8B	1.293 (3)
N3A—C4A	1.420 (3)	N3B—C4B	1.416 (3)
C2A—C3A	1.374 (3)	C2B—C3B	1.387 (3)
C2A—C7A	1.405 (3)	C2B—C7B	1.392 (3)
C3A—C4A	1.402 (3)	C3B—C4B	1.398 (3)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.408 (3)	C4B—C5B	1.408 (3)
C5A—C6A	1.387 (3)	C5B—C6B	1.374 (3)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.381 (3)	C6B—C7B	1.392 (3)
C6A—H6AA	0.9300	C6B—H6BA	0.9300
C8A—C9A	1.447 (3)	C8B—C9B	1.438 (3)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.405 (3)	C9B—C10B	1.404 (3)
C9A—C14A	1.409 (3)	C9B—C14B	1.415 (3)
C10A—C11A	1.368 (3)	C10B—C11B	1.372 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.393 (3)	C11B—C12B	1.396 (3)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.388 (3)	C12B—C13B	1.383 (3)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.384 (3)	C13B—C14B	1.390 (3)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—O1A—H1OA	108 (2)	C14B—O1B—H1OB	105 (2)
C1A—N1A—C7A	110.31 (18)	C1B—N1B—C2B	110.49 (17)
C1A—N1A—H1NA	125 (2)	C1B—N1B—H1NB	124.5 (16)
C7A—N1A—H1NA	125 (2)	C2B—N1B—H1NB	124.8 (16)
C1A—N2A—C2A	110.80 (18)	C1B—N2B—C7B	110.32 (18)
C1A—N2A—H2NA	122.8 (18)	C1B—N2B—H2NB	122.1 (19)
C2A—N2A—H2NA	125.0 (18)	C7B—N2B—H2NB	127.5 (19)
C8A—N3A—C4A	121.14 (18)	C8B—N3B—C4B	122.41 (18)
N2A—C1A—N1A	106.66 (19)	N1B—C1B—N2B	106.32 (18)
N2A—C1A—S1A	125.40 (16)	N1B—C1B—S1B	127.87 (16)
N1A—C1A—S1A	127.91 (17)	N2B—C1B—S1B	125.81 (17)
C3A—C2A—N2A	131.86 (19)	C3B—C2B—C7B	121.93 (19)
C3A—C2A—C7A	122.13 (19)	C3B—C2B—N1B	132.46 (18)
N2A—C2A—C7A	106.01 (18)	C7B—C2B—N1B	105.60 (19)
C2A—C3A—C4A	117.38 (19)	C2B—C3B—C4B	116.88 (18)
C2A—C3A—H3AA	121.3	C2B—C3B—H3BA	121.6
C4A—C3A—H3AA	121.3	C4B—C3B—H3BA	121.6
C3A—C4A—C5A	120.2 (2)	C3B—C4B—C5B	120.9 (2)
C3A—C4A—N3A	124.00 (19)	C3B—C4B—N3B	116.39 (18)
C5A—C4A—N3A	115.81 (18)	C5B—C4B—N3B	122.72 (18)
C6A—C5A—C4A	122.0 (2)	C6B—C5B—C4B	121.63 (19)
C6A—C5A—H5AA	119.0	C6B—C5B—H5BA	119.2
C4A—C5A—H5AA	119.0	C4B—C5B—H5BA	119.2
C7A—C6A—C5A	117.28 (19)	C5B—C6B—C7B	117.51 (19)
C7A—C6A—H6AA	121.4	C5B—C6B—H6BA	121.2
C5A—C6A—H6AA	121.4	C7B—C6B—H6BA	121.2
C6A—C7A—N1A	132.74 (19)	N2B—C7B—C6B	131.55 (19)
C6A—C7A—C2A	121.0 (2)	N2B—C7B—C2B	107.26 (18)
N1A—C7A—C2A	106.21 (18)	C6B—C7B—C2B	121.2 (2)
N3A—C8A—C9A	121.52 (19)	N3B—C8B—C9B	121.54 (19)
N3A—C8A—H8AA	119.2	N3B—C8B—H8BA	119.2
C9A—C8A—H8AA	119.2	C9B—C8B—H8BA	119.2
C10A—C9A—C14A	118.4 (2)	C10B—C9B—C14B	118.0 (2)
C10A—C9A—C8A	119.47 (19)	C10B—C9B—C8B	121.02 (19)
C14A—C9A—C8A	122.10 (19)	C14B—C9B—C8B	120.99 (19)
C11A—C10A—C9A	121.2 (2)	C11B—C10B—C9B	121.8 (2)
C11A—C10A—H10A	119.4	C11B—C10B—H10B	119.1
C9A—C10A—H10A	119.4	C9B—C10B—H10B	119.1
C10A—C11A—C12A	119.6 (2)	C10B—C11B—C12B	119.0 (2)
C10A—C11A—H11A	120.2	C10B—C11B—H11B	120.5
C12A—C11A—H11A	120.2	C12B—C11B—H11B	120.5
C13A—C12A—C11A	120.7 (2)	C13B—C12B—C11B	121.0 (2)
C13A—C12A—H12A	119.6	C13B—C12B—H12B	119.5
C11A—C12A—H12A	119.6	C11B—C12B—H12B	119.5
C14A—C13A—C12A	119.7 (2)	C12B—C13B—C14B	119.8 (2)
C14A—C13A—H13A	120.2	C12B—C13B—H13B	120.1
C12A—C13A—H13A	120.2	C14B—C13B—H13B	120.1
O1A—C14A—C13A	118.99 (19)	O1B—C14B—C13B	119.24 (19)
O1A—C14A—C9A	120.7 (2)	O1B—C14B—C9B	120.5 (2)
C13A—C14A—C9A	120.29 (19)	C13B—C14B—C9B	120.29 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···S1Bi	0.86 (3)	2.61 (3)	3.4714 (19)	173 (3)
N2A—H2NA···O1Bii	0.86 (3)	1.99 (3)	2.781 (2)	153 (3)
N1B—H1NB···O1Aiii	0.87 (2)	2.16 (2)	2.936 (2)	149 (2)
N2B—H2NB···S1Aiv	0.84 (3)	2.45 (3)	3.2547 (19)	163 (2)
O1B—H1OB···N3B	0.99 (4)	1.64 (3)	2.552 (2)	152 (3)
O1A—H1OA···N3A	0.99 (4)	1.72 (4)	2.600 (3)	147 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯S1Bi	0.86 (3)	2.61 (3)	3.4714 (19)	173 (3)
N2A—H2NA⋯O1Bii	0.86 (3)	1.99 (3)	2.781 (2)	153 (3)
N1B—H1NB⋯O1Aiii	0.87 (2)	2.16 (2)	2.936 (2)	149 (2)
N2B—H2NB⋯S1Aiv	0.84 (3)	2.45 (3)	3.2547 (19)	163 (2)
O1B—H1OB⋯N3B	0.99 (4)	1.64 (3)	2.552 (2)	152 (3)
O1A—H1OA⋯N3A	0.99 (4)	1.72 (4)	2.600 (3)	147 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .