2-Methyl-benzimidazolium thio-cyanate-2-methyl-benzimidazole (1/1).

In the crystal structure of the title compound, C(8)H(9)N(2) (+)·SCN(-)·C(8)H(8)N(2), the three components are linked by inter-molecular N-H⋯N and N-H⋯S hydrogen bonds into infinite chains along the c axis.

Related literature

For related structures, see: Bhattacharya et al. (2004 ▶); Ding et al. (2004 ▶); Huang et al. (2006 ▶). For applications of benzimidazole derivatives in crystal engineering, see: Cai et al. (2002 ▶). For the biological properties of benzimidazole derivatives, see: Refaat (2010 ▶); Ansari & Lal (2009 ▶).

Experimental

Crystal data

C8H9N2 +·SCN−·C8H8N2

M = 323.42

Monoclinic,

a = 11.0952 (7) Å

b = 6.9664 (4) Å

c = 21.4195 (13) Å

β = 100.745 (1)°

V = 1626.56 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.25 × 0.25 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.950, T max = 0.988

8812 measured reflections

3193 independent reflections

2427 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.093

S = 1.03

3193 reflections

222 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810031181/pv2314sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031181/pv2314Isup2.hkl

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

C8H9N2+·SCN−·C8H8N2	F(000) = 680
Mr = 323.42	Dx = 1.321 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1739 reflections
a = 11.0952 (7) Å	θ = 2.3–25.1°
b = 6.9664 (4) Å	µ = 0.21 mm−1
c = 21.4195 (13) Å	T = 100 K
β = 100.745 (1)°	Plate, yellow
V = 1626.56 (17) Å3	0.25 × 0.25 × 0.06 mm
Z = 4

Bruker APEXII CCD diffractometer	3193 independent reflections
Radiation source: fine-focus sealed tube	2427 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.950, Tmax = 0.988	k = −7→8
8812 measured reflections	l = −26→26

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.035P)2 + 0.6349P] where P = (Fo2 + 2Fc2)/3
3193 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.20 e Å−3
3 restraints	Δρmin = −0.28 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
N1	0.76009 (14)	0.1676 (2)	0.43464 (7)	0.0183 (4)
H1N	0.7853 (18)	0.196 (3)	0.4761 (8)	0.033 (6)*
N2	0.76652 (13)	0.1089 (2)	0.33548 (7)	0.0169 (3)
H2N	0.7976 (19)	0.090 (3)	0.2999 (8)	0.038 (7)*
C1	0.96598 (16)	0.1988 (3)	0.40543 (9)	0.0233 (4)
H1A	1.0105	0.0784	0.4165	0.035*
H1B	0.9851	0.2889	0.4410	0.035*
H1C	0.9908	0.2546	0.3678	0.035*
C2	0.83267 (16)	0.1602 (3)	0.39179 (8)	0.0174 (4)
C3	0.64561 (16)	0.0800 (3)	0.34260 (9)	0.0170 (4)
C4	0.54091 (16)	0.0242 (3)	0.29996 (9)	0.0198 (4)
H4	0.5429	−0.0024	0.2567	0.024*
C5	0.43398 (17)	0.0096 (3)	0.32393 (10)	0.0244 (5)
H5	0.3608	−0.0290	0.2963	0.029*
C6	0.43008 (17)	0.0498 (3)	0.38747 (10)	0.0262 (5)
H6	0.3545	0.0381	0.4019	0.031*
C7	0.53387 (17)	0.1064 (3)	0.42968 (10)	0.0227 (4)
H7	0.5317	0.1352	0.4728	0.027*
C8	0.64148 (16)	0.1190 (3)	0.40569 (9)	0.0173 (4)
N3	0.49936 (14)	0.4693 (2)	0.66246 (7)	0.0179 (3)
H3N	0.5709 (14)	0.483 (3)	0.6527 (9)	0.022 (5)*
N4	0.36143 (13)	0.4455 (2)	0.72545 (7)	0.0175 (3)
C9	0.57509 (16)	0.5348 (3)	0.77709 (9)	0.0236 (4)
H9A	0.5377	0.5843	0.8119	0.035*
H9B	0.6283	0.6334	0.7640	0.035*
H9C	0.6239	0.4205	0.7915	0.035*
C10	0.47689 (16)	0.4834 (3)	0.72223 (9)	0.0174 (4)
C11	0.39134 (16)	0.4178 (3)	0.62290 (9)	0.0173 (4)
C12	0.36142 (17)	0.3839 (3)	0.55802 (9)	0.0212 (4)
H12	0.4209	0.3944	0.5315	0.025*
C13	0.24092 (18)	0.3343 (3)	0.53365 (9)	0.0235 (4)
H13	0.2171	0.3092	0.4895	0.028*
C14	0.15347 (18)	0.3204 (3)	0.57299 (9)	0.0239 (4)
H14	0.0715	0.2865	0.5549	0.029*
C15	0.18384 (16)	0.3548 (3)	0.63752 (9)	0.0204 (4)
H15	0.1240	0.3455	0.6638	0.024*
C16	0.30494 (16)	0.4037 (3)	0.66294 (8)	0.0167 (4)
S1	0.79070 (4)	0.52630 (8)	0.64995 (2)	0.02656 (15)
N5	0.83250 (16)	0.2375 (3)	0.56491 (8)	0.0283 (4)
C17	0.81466 (16)	0.3567 (3)	0.60007 (9)	0.0208 (4)

	U11	U22	U33	U12	U13	U23
N1	0.0217 (8)	0.0189 (9)	0.0143 (8)	0.0006 (7)	0.0030 (6)	−0.0004 (7)
N2	0.0162 (8)	0.0193 (9)	0.0156 (8)	0.0004 (6)	0.0041 (6)	−0.0006 (7)
C1	0.0184 (10)	0.0266 (12)	0.0237 (10)	0.0000 (8)	0.0006 (8)	−0.0034 (9)
C2	0.0200 (9)	0.0152 (10)	0.0169 (9)	0.0024 (7)	0.0029 (7)	0.0009 (8)
C3	0.0186 (9)	0.0132 (10)	0.0198 (10)	0.0019 (7)	0.0051 (7)	0.0022 (8)
C4	0.0197 (9)	0.0175 (10)	0.0210 (10)	0.0005 (8)	0.0008 (7)	0.0007 (9)
C5	0.0181 (9)	0.0196 (11)	0.0343 (12)	−0.0004 (8)	0.0016 (8)	0.0046 (9)
C6	0.0213 (10)	0.0226 (11)	0.0380 (12)	0.0022 (8)	0.0145 (9)	0.0068 (10)
C7	0.0283 (11)	0.0180 (11)	0.0248 (10)	0.0030 (8)	0.0125 (8)	0.0040 (9)
C8	0.0197 (9)	0.0115 (10)	0.0207 (10)	0.0015 (7)	0.0043 (7)	0.0028 (8)
N3	0.0143 (8)	0.0202 (9)	0.0205 (8)	0.0002 (7)	0.0063 (6)	0.0005 (7)
N4	0.0178 (8)	0.0181 (9)	0.0165 (8)	−0.0002 (6)	0.0031 (6)	0.0013 (7)
C9	0.0197 (10)	0.0262 (11)	0.0242 (10)	−0.0011 (8)	0.0021 (8)	−0.0001 (9)
C10	0.0180 (9)	0.0149 (10)	0.0193 (9)	0.0001 (7)	0.0032 (7)	−0.0002 (8)
C11	0.0192 (9)	0.0131 (10)	0.0193 (9)	0.0011 (7)	0.0027 (7)	0.0009 (8)
C12	0.0291 (10)	0.0159 (10)	0.0201 (10)	0.0016 (8)	0.0083 (8)	0.0022 (8)
C13	0.0328 (11)	0.0177 (11)	0.0177 (10)	−0.0005 (9)	−0.0011 (8)	0.0000 (9)
C14	0.0230 (10)	0.0202 (11)	0.0258 (11)	−0.0027 (8)	−0.0018 (8)	0.0027 (9)
C15	0.0182 (9)	0.0188 (11)	0.0240 (10)	−0.0017 (8)	0.0032 (8)	0.0029 (9)
C16	0.0213 (9)	0.0126 (9)	0.0159 (9)	0.0023 (7)	0.0025 (7)	0.0027 (8)
S1	0.0226 (3)	0.0293 (3)	0.0296 (3)	−0.0040 (2)	0.0095 (2)	−0.0066 (2)
N5	0.0336 (10)	0.0324 (11)	0.0184 (9)	0.0026 (8)	0.0033 (7)	−0.0006 (8)
C17	0.0166 (9)	0.0285 (12)	0.0165 (9)	−0.0007 (8)	0.0010 (7)	0.0060 (9)

N1—C2	1.330 (2)	N3—C11	1.380 (2)
N1—C8	1.388 (2)	N3—H3N	0.862 (15)
N1—H1N	0.901 (15)	N4—C10	1.322 (2)
N2—C2	1.338 (2)	N4—C16	1.399 (2)
N2—C3	1.393 (2)	C9—C10	1.489 (2)
N2—H2N	0.902 (15)	C9—H9A	0.9800
C1—C2	1.478 (2)	C9—H9B	0.9800
C1—H1A	0.9800	C9—H9C	0.9800
C1—H1B	0.9800	C11—C12	1.387 (3)
C1—H1C	0.9800	C11—C16	1.404 (3)
C3—C8	1.387 (2)	C12—C13	1.385 (3)
C3—C4	1.392 (2)	C12—H12	0.9500
C4—C5	1.381 (3)	C13—C14	1.402 (3)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.398 (3)	C14—C15	1.381 (3)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.382 (3)	C15—C16	1.395 (2)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.388 (3)	S1—C17	1.647 (2)
C7—H7	0.9500	N5—C17	1.163 (2)
N3—C10	1.353 (2)
C2—N1—C8	109.14 (15)	C10—N3—C11	107.93 (15)
C2—N1—H1N	124.9 (13)	C10—N3—H3N	124.1 (13)
C8—N1—H1N	125.9 (13)	C11—N3—H3N	127.8 (13)
C2—N2—C3	108.51 (15)	C10—N4—C16	104.90 (15)
C2—N2—H2N	124.6 (14)	C10—C9—H9A	109.5
C3—N2—H2N	126.8 (14)	C10—C9—H9B	109.5
C2—C1—H1A	109.5	H9A—C9—H9B	109.5
C2—C1—H1B	109.5	C10—C9—H9C	109.5
H1A—C1—H1B	109.5	H9A—C9—H9C	109.5
C2—C1—H1C	109.5	H9B—C9—H9C	109.5
H1A—C1—H1C	109.5	N4—C10—N3	112.71 (15)
H1B—C1—H1C	109.5	N4—C10—C9	125.46 (17)
N1—C2—N2	109.35 (15)	N3—C10—C9	121.82 (16)
N1—C2—C1	124.67 (16)	N3—C11—C12	132.64 (17)
N2—C2—C1	125.96 (17)	N3—C11—C16	104.88 (16)
C8—C3—C4	121.23 (17)	C12—C11—C16	122.48 (17)
C8—C3—N2	106.61 (15)	C13—C12—C11	116.98 (17)
C4—C3—N2	132.17 (17)	C13—C12—H12	121.5
C5—C4—C3	116.49 (18)	C11—C12—H12	121.5
C5—C4—H4	121.8	C12—C13—C14	121.20 (18)
C3—C4—H4	121.8	C12—C13—H13	119.4
C4—C5—C6	122.11 (18)	C14—C13—H13	119.4
C4—C5—H5	118.9	C15—C14—C13	121.49 (18)
C6—C5—H5	118.9	C15—C14—H14	119.3
C7—C6—C5	121.38 (18)	C13—C14—H14	119.3
C7—C6—H6	119.3	C14—C15—C16	118.08 (17)
C5—C6—H6	119.3	C14—C15—H15	121.0
C6—C7—C8	116.43 (18)	C16—C15—H15	121.0
C6—C7—H7	121.8	C15—C16—N4	130.66 (17)
C8—C7—H7	121.8	C15—C16—C11	119.76 (17)
C3—C8—C7	122.36 (17)	N4—C16—C11	109.58 (15)
C3—C8—N1	106.39 (15)	N5—C17—S1	179.47 (18)
C7—C8—N1	131.25 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N5	0.90 (2)	1.90 (2)	2.799 (2)	176 (2)
N2—H2N···N4i	0.90 (2)	1.88 (2)	2.781 (2)	179 (2)
N3—H3N···S1	0.86 (2)	2.47 (2)	3.317 (2)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N5	0.90 (2)	1.90 (2)	2.799 (2)	176 (2)
N2—H2N⋯N4i	0.90 (2)	1.88 (2)	2.781 (2)	179 (2)
N3—H3N⋯S1	0.86 (2)	2.47 (2)	3.317 (2)	168 (2)

Symmetry code: (i) .