1-[(1-Methyl-1H-imidazol-5-yl)meth-yl]-1H-indole-5-carbonitrile.

In the title compound, C14H12N4, the dihedral angle between the indole ring system (r.m.s. deviation = 0.010 Å) and the imidazole ring is 77.70 (6)°. In the crystal, mol-ecules are linked by C-H⋯N hydrogen bonds. One set of hydrogen bonds forms an undulating chain running parallel to the b-axis direction, while the other undulating chain is parallel to the c-axis direction. In combination, (100) sheets result.

Related literature

For background to farnesyl transferase, see: Chakrabarti et al. (2002 ▶). For the properties of related compounds, see: Bulbule et al. (2008 ▶), van Voorhis et al. (2007 ▶); de Ruyck & Wouters (2008 ▶).

Experimental

Crystal data

C14H12N4

M = 236.28

Monoclinic,

a = 10.9624 (16) Å

b = 7.8687 (12) Å

c = 14.292 (2) Å

β = 106.727 (2)°

V = 1180.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.10 × 0.10 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.992, T max = 0.998

36857 measured reflections

3286 independent reflections

2643 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.06

3286 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 ▶; Atwood et al., 2003 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048404/hb7000sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048404/hb7000Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048404/hb7000Isup3.cml

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

C14H12N4	F(000) = 496
Mr = 236.28	Dx = 1.329 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7965 reflections
a = 10.9624 (16) Å	θ = 3.0–28.6°
b = 7.8687 (12) Å	µ = 0.08 mm−1
c = 14.292 (2) Å	T = 100 K
β = 106.727 (2)°	Plate, colourless
V = 1180.6 (3) Å3	0.10 × 0.10 × 0.02 mm
Z = 4

Bruker APEXII CCD diffractometer	3286 independent reflections
Radiation source: fine-focus sealed tube, Bruker Apex2	2643 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 29.8°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.992, Tmax = 0.998	k = −10→10
36857 measured reflections	l = −19→19

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.613P] where P = (Fo2 + 2Fc2)/3
3286 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.21 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	0.74899 (9)	0.05550 (13)	0.10401 (7)	0.0182 (2)
C8	0.63632 (11)	0.14156 (15)	0.06741 (8)	0.0172 (2)
C3	0.57779 (11)	0.15677 (15)	0.14387 (8)	0.0182 (2)
N3	1.05057 (10)	0.09402 (14)	0.16447 (8)	0.0204 (2)
N4	1.15865 (10)	−0.14899 (14)	0.18381 (8)	0.0218 (2)
C6	0.46523 (12)	0.28892 (17)	−0.04359 (9)	0.0222 (3)
H6	0.4248	0.3338	−0.1066	0.027*
C9	0.28834 (12)	0.40021 (18)	0.01344 (10)	0.0253 (3)
C13	1.16216 (12)	0.01364 (17)	0.20734 (9)	0.0213 (3)
H13	1.2346	0.0681	0.2495	0.026*
C2	0.66051 (12)	0.07444 (16)	0.22788 (9)	0.0202 (2)
H2	0.6472	0.0638	0.2904	0.024*
N2	0.19352 (11)	0.47248 (17)	−0.00085 (10)	0.0327 (3)
C4	0.46133 (12)	0.24195 (16)	0.12543 (9)	0.0206 (3)
H4	0.4203	0.2545	0.1752	0.025*
C1	0.76221 (12)	0.01428 (16)	0.20058 (9)	0.0201 (2)
H1	0.8318	−0.0469	0.2419	0.024*
C12	1.03687 (12)	−0.17490 (17)	0.12259 (9)	0.0209 (3)
H12	1.0050	−0.2807	0.0937	0.025*
C7	0.58051 (11)	0.20564 (16)	−0.02668 (9)	0.0201 (2)
H7	0.6205	0.1923	−0.0770	0.024*
C5	0.40688 (11)	0.30803 (16)	0.03208 (9)	0.0213 (3)
C10	0.83783 (11)	0.01570 (18)	0.04742 (9)	0.0214 (3)
H10A	0.8426	0.1144	0.0056	0.026*
H10B	0.8041	−0.0819	0.0039	0.026*
C11	0.96882 (11)	−0.02628 (16)	0.10955 (9)	0.0195 (2)
C14	1.02309 (13)	0.27356 (18)	0.17436 (11)	0.0296 (3)
H14A	1.0997	0.3305	0.2147	0.044*
H14C	0.9546	0.2842	0.2054	0.044*
H14B	0.9965	0.3265	0.1096	0.044*

	U11	U22	U33	U12	U13	U23
N1	0.0142 (5)	0.0216 (5)	0.0177 (5)	0.0003 (4)	0.0028 (4)	0.0016 (4)
C8	0.0135 (5)	0.0176 (5)	0.0192 (5)	−0.0028 (4)	0.0028 (4)	−0.0013 (4)
C3	0.0169 (5)	0.0178 (5)	0.0189 (5)	−0.0030 (4)	0.0035 (4)	−0.0017 (4)
N3	0.0158 (5)	0.0211 (5)	0.0230 (5)	0.0004 (4)	0.0033 (4)	0.0003 (4)
N4	0.0183 (5)	0.0244 (5)	0.0221 (5)	0.0015 (4)	0.0048 (4)	0.0025 (4)
C6	0.0197 (6)	0.0224 (6)	0.0199 (6)	−0.0009 (5)	−0.0014 (4)	0.0008 (5)
C9	0.0199 (6)	0.0251 (6)	0.0276 (6)	−0.0005 (5)	0.0013 (5)	−0.0026 (5)
C13	0.0152 (5)	0.0254 (6)	0.0222 (6)	0.0007 (5)	0.0037 (4)	0.0019 (5)
C2	0.0197 (6)	0.0218 (6)	0.0182 (5)	−0.0017 (5)	0.0042 (4)	0.0006 (4)
N2	0.0222 (6)	0.0324 (7)	0.0392 (7)	0.0041 (5)	0.0019 (5)	−0.0023 (5)
C4	0.0171 (5)	0.0215 (6)	0.0222 (6)	−0.0026 (5)	0.0043 (4)	−0.0040 (5)
C1	0.0188 (6)	0.0215 (6)	0.0183 (5)	−0.0001 (5)	0.0026 (4)	0.0024 (4)
C12	0.0188 (6)	0.0235 (6)	0.0207 (6)	−0.0010 (5)	0.0063 (4)	−0.0009 (5)
C7	0.0181 (6)	0.0224 (6)	0.0187 (5)	−0.0018 (5)	0.0033 (4)	−0.0001 (5)
C5	0.0150 (5)	0.0202 (6)	0.0256 (6)	−0.0004 (5)	0.0008 (4)	−0.0025 (5)
C10	0.0148 (5)	0.0305 (7)	0.0184 (5)	0.0006 (5)	0.0041 (4)	0.0000 (5)
C11	0.0152 (5)	0.0244 (6)	0.0185 (5)	−0.0015 (5)	0.0043 (4)	−0.0003 (4)
C14	0.0233 (6)	0.0215 (6)	0.0402 (8)	0.0016 (5)	0.0031 (6)	−0.0026 (6)

N1—C8	1.3733 (15)	C9—C5	1.4445 (18)
N1—C1	1.3842 (15)	C13—H13	0.9500
N1—C10	1.4676 (15)	C2—C1	1.3673 (17)
C8—C7	1.4011 (16)	C2—H2	0.9500
C8—C3	1.4226 (16)	C4—C5	1.3958 (18)
C3—C4	1.3982 (17)	C4—H4	0.9500
C3—C2	1.4341 (17)	C1—H1	0.9500
N3—C13	1.3567 (16)	C12—C11	1.3707 (18)
N3—C11	1.3822 (16)	C12—H12	0.9500
N3—C14	1.4598 (17)	C7—H7	0.9500
N4—C13	1.3209 (17)	C10—C11	1.4918 (17)
N4—C12	1.3845 (16)	C10—H10A	0.9900
C6—C7	1.3817 (17)	C10—H10B	0.9900
C6—C5	1.4140 (18)	C14—H14A	0.9800
C6—H6	0.9500	C14—H14C	0.9800
C9—N2	1.1504 (18)	C14—H14B	0.9800
C8—N1—C1	108.65 (10)	C2—C1—H1	125.0
C8—N1—C10	124.20 (10)	N1—C1—H1	125.0
C1—N1—C10	127.14 (10)	C11—C12—N4	110.39 (11)
N1—C8—C7	129.75 (11)	C11—C12—H12	124.8
N1—C8—C3	107.70 (10)	N4—C12—H12	124.8
C7—C8—C3	122.55 (11)	C6—C7—C8	117.60 (11)
C4—C3—C8	119.00 (11)	C6—C7—H7	121.2
C4—C3—C2	134.22 (11)	C8—C7—H7	121.2
C8—C3—C2	106.78 (10)	C4—C5—C6	121.89 (11)
C13—N3—C11	106.87 (11)	C4—C5—C9	118.55 (12)
C13—N3—C14	126.29 (11)	C6—C5—C9	119.56 (12)
C11—N3—C14	126.84 (11)	N1—C10—C11	113.39 (10)
C13—N4—C12	104.82 (11)	N1—C10—H10A	108.9
C7—C6—C5	120.60 (11)	C11—C10—H10A	108.9
C7—C6—H6	119.7	N1—C10—H10B	108.9
C5—C6—H6	119.7	C11—C10—H10B	108.9
N2—C9—C5	179.32 (16)	H10A—C10—H10B	107.7
N4—C13—N3	112.35 (11)	C12—C11—N3	105.58 (11)
N4—C13—H13	123.8	C12—C11—C10	131.51 (12)
N3—C13—H13	123.8	N3—C11—C10	122.82 (11)
C1—C2—C3	106.77 (11)	N3—C14—H14A	109.5
C1—C2—H2	126.6	N3—C14—H14C	109.5
C3—C2—H2	126.6	H14A—C14—H14C	109.5
C5—C4—C3	118.35 (11)	N3—C14—H14B	109.5
C5—C4—H4	120.8	H14A—C14—H14B	109.5
C3—C4—H4	120.8	H14C—C14—H14B	109.5
C2—C1—N1	110.09 (11)
C1—N1—C8—C7	−178.49 (12)	C13—N4—C12—C11	0.44 (14)
C10—N1—C8—C7	1.3 (2)	C5—C6—C7—C8	0.08 (18)
C1—N1—C8—C3	0.78 (13)	N1—C8—C7—C6	−179.67 (12)
C10—N1—C8—C3	−179.46 (11)	C3—C8—C7—C6	1.15 (18)
N1—C8—C3—C4	179.29 (11)	C3—C4—C5—C6	0.89 (18)
C7—C8—C3—C4	−1.37 (18)	C3—C4—C5—C9	−178.31 (11)
N1—C8—C3—C2	−0.42 (13)	C7—C6—C5—C4	−1.11 (19)
C7—C8—C3—C2	178.91 (11)	C7—C6—C5—C9	178.07 (12)
C12—N4—C13—N3	−0.46 (14)	C8—N1—C10—C11	161.26 (11)
C11—N3—C13—N4	0.31 (14)	C1—N1—C10—C11	−19.02 (18)
C14—N3—C13—N4	−179.36 (12)	N4—C12—C11—N3	−0.26 (14)
C4—C3—C2—C1	−179.75 (14)	N4—C12—C11—C10	176.39 (12)
C8—C3—C2—C1	−0.09 (14)	C13—N3—C11—C12	−0.02 (13)
C8—C3—C4—C5	0.32 (17)	C14—N3—C11—C12	179.65 (12)
C2—C3—C4—C5	179.95 (13)	C13—N3—C11—C10	−177.03 (11)
C3—C2—C1—N1	0.58 (14)	C14—N3—C11—C10	2.63 (19)
C8—N1—C1—C2	−0.86 (14)	N1—C10—C11—C12	112.73 (15)
C10—N1—C1—C2	179.39 (11)	N1—C10—C11—N3	−71.12 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N4i	0.95	2.53	3.4588 (18)	167
C13—H13···N4ii	0.95	2.57	3.4010 (18)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N4i	0.95	2.53	3.4588 (18)	167
C13—H13⋯N4ii	0.95	2.57	3.4010 (18)	147

Symmetry codes: (i) ; (ii) .