2-[(1-Methyl-1H-pyrrol-2-yl)methyl-idene]propane-dinitrile.

In the title compound, C(9)H(7)N(3), the N-bound methyl group and vinyl H atom are syn. The 12 non-H atoms comprising the mol-ecule are essentially coplanar (r.m.s. deviation = 0.071 Å). Supra-molecular tapes feature in the crystal packing, orientated perpendicular to [10-1], and are formed by C-H⋯N inter-actions involving each cyano N atom. The tapes are connected into layers via π-π inter-actions occurring between translationally related pyrrole rings [ring centroid-centroid distance = 3.8754 (10) Å]; the layers stack along the b axis.

Related literature

For the anti-cancer effects of related compounds, see: Rostom et al. (2011 ▶). For structural studies of di-carbonitrile compounds, see: Asiri et al. (2011 ▶); Al-Youbi et al. (2012 ▶).

Experimental

Crystal data

C9H7N3

M = 157.18

Triclinic,

a = 3.8754 (2) Å

b = 8.7795 (5) Å

c = 12.1773 (7) Å

α = 97.517 (5)°

β = 90.962 (5)°

γ = 98.689 (5)°

V = 405.76 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.25 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.980, T max = 0.996

5871 measured reflections

1866 independent reflections

1463 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.01

1866 reflections

137 parameters

All H-atom parameters refined

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201197X/bt5851sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201197X/bt5851Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201197X/bt5851Isup3.cml

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

C9H7N3	Z = 2
Mr = 157.18	F(000) = 164
Triclinic, P1	Dx = 1.286 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8754 (2) Å	Cell parameters from 1724 reflections
b = 8.7795 (5) Å	θ = 2.4–27.5°
c = 12.1773 (7) Å	µ = 0.08 mm−1
α = 97.517 (5)°	T = 100 K
β = 90.962 (5)°	Prism, light-brown
γ = 98.689 (5)°	0.25 × 0.15 × 0.05 mm
V = 405.76 (4) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	1866 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1463 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.039
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.4°
ω scan	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→11
Tmin = 0.980, Tmax = 0.996	l = −15→15
5871 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	All H-atom parameters refined
S = 1.01	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.1622P] where P = (Fo2 + 2Fc2)/3
1866 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.3583 (3)	0.18886 (15)	0.26433 (10)	0.0202 (3)
N2	0.2317 (4)	0.71488 (16)	0.02337 (11)	0.0267 (3)
N3	0.8617 (4)	0.78536 (16)	0.32981 (11)	0.0267 (3)
C1	0.1644 (5)	0.0922 (2)	0.16953 (14)	0.0250 (4)
C2	0.4697 (4)	0.13538 (19)	0.35574 (13)	0.0234 (4)
C3	0.6539 (4)	0.25848 (19)	0.42647 (13)	0.0246 (4)
C4	0.6548 (4)	0.39208 (19)	0.37650 (12)	0.0220 (4)
C5	0.4681 (4)	0.34899 (17)	0.27400 (12)	0.0188 (3)
C6	0.3763 (4)	0.43469 (17)	0.19062 (12)	0.0185 (3)
C7	0.4655 (4)	0.59152 (18)	0.18566 (12)	0.0190 (3)
C8	0.3370 (4)	0.65898 (17)	0.09541 (12)	0.0202 (3)
C9	0.6828 (4)	0.69787 (17)	0.26673 (12)	0.0196 (3)
H11	0.106 (5)	−0.015 (3)	0.1842 (17)	0.041 (6)*
H12	0.308 (5)	0.090 (2)	0.1053 (17)	0.038 (5)*
H13	−0.050 (5)	0.132 (2)	0.1524 (16)	0.033 (5)*
H2	0.412 (5)	0.027 (2)	0.3608 (15)	0.025 (4)*
H3	0.763 (5)	0.250 (2)	0.4978 (16)	0.031 (5)*
H4	0.769 (5)	0.500 (2)	0.4051 (14)	0.024 (4)*
H6	0.220 (4)	0.378 (2)	0.1311 (14)	0.020 (4)*

	U11	U22	U33	U12	U13	U23
N1	0.0225 (7)	0.0198 (7)	0.0189 (6)	0.0031 (5)	0.0018 (5)	0.0047 (5)
N2	0.0320 (8)	0.0269 (7)	0.0215 (7)	0.0040 (6)	−0.0007 (6)	0.0056 (6)
N3	0.0310 (8)	0.0241 (7)	0.0245 (7)	0.0008 (6)	−0.0021 (6)	0.0062 (6)
C1	0.0282 (9)	0.0221 (8)	0.0235 (8)	0.0002 (7)	−0.0013 (7)	0.0037 (6)
C2	0.0255 (8)	0.0227 (8)	0.0244 (8)	0.0054 (6)	0.0050 (6)	0.0097 (6)
C3	0.0254 (8)	0.0301 (9)	0.0201 (8)	0.0054 (7)	0.0008 (6)	0.0089 (6)
C4	0.0209 (8)	0.0249 (8)	0.0204 (8)	0.0024 (6)	0.0018 (6)	0.0046 (6)
C5	0.0188 (7)	0.0196 (7)	0.0182 (7)	0.0022 (6)	0.0029 (6)	0.0045 (6)
C6	0.0179 (7)	0.0213 (8)	0.0163 (7)	0.0034 (6)	0.0018 (6)	0.0023 (6)
C7	0.0195 (7)	0.0221 (8)	0.0162 (7)	0.0042 (6)	0.0023 (6)	0.0041 (6)
C8	0.0214 (8)	0.0201 (7)	0.0191 (8)	0.0028 (6)	0.0022 (6)	0.0023 (6)
C9	0.0208 (7)	0.0201 (7)	0.0198 (8)	0.0041 (6)	0.0037 (6)	0.0079 (6)

N1—C2	1.352 (2)	C3—C4	1.390 (2)
N1—C5	1.3949 (19)	C3—H3	0.977 (19)
N1—C1	1.463 (2)	C4—C5	1.410 (2)
N2—C8	1.157 (2)	C4—H4	1.002 (19)
N3—C9	1.152 (2)	C5—C6	1.412 (2)
C1—H11	0.97 (2)	C6—C7	1.378 (2)
C1—H12	0.97 (2)	C6—H6	0.969 (17)
C1—H13	0.98 (2)	C7—C8	1.431 (2)
C2—C3	1.386 (2)	C7—C9	1.431 (2)
C2—H2	0.952 (19)
C2—N1—C5	108.97 (13)	C3—C4—C5	107.69 (14)
C2—N1—C1	124.98 (13)	C3—C4—H4	127.8 (10)
C5—N1—C1	126.02 (13)	C5—C4—H4	124.5 (10)
N1—C1—H11	110.6 (12)	N1—C5—C4	106.64 (13)
N1—C1—H12	109.7 (11)	N1—C5—C6	120.42 (13)
H11—C1—H12	106.9 (17)	C4—C5—C6	132.91 (14)
N1—C1—H13	111.0 (11)	C7—C6—C5	128.23 (14)
H11—C1—H13	109.4 (17)	C7—C6—H6	115.2 (10)
H12—C1—H13	109.2 (16)	C5—C6—H6	116.5 (10)
N1—C2—C3	109.17 (14)	C6—C7—C8	120.18 (13)
N1—C2—H2	118.3 (11)	C6—C7—C9	124.54 (13)
C3—C2—H2	132.5 (11)	C8—C7—C9	115.29 (13)
C2—C3—C4	107.53 (14)	N2—C8—C7	179.15 (16)
C2—C3—H3	125.1 (11)	N3—C9—C7	178.23 (16)
C4—C3—H3	127.3 (11)
C5—N1—C2—C3	−0.11 (17)	C1—N1—C5—C6	3.9 (2)
C1—N1—C2—C3	177.99 (14)	C3—C4—C5—N1	−0.10 (17)
N1—C2—C3—C4	0.05 (18)	C3—C4—C5—C6	177.75 (16)
C2—C3—C4—C5	0.04 (18)	N1—C5—C6—C7	−178.89 (14)
C2—N1—C5—C4	0.13 (17)	C4—C5—C6—C7	3.5 (3)
C1—N1—C5—C4	−177.94 (14)	C5—C6—C7—C8	−177.93 (14)
C2—N1—C5—C6	−178.05 (13)	C5—C6—C7—C9	1.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N3i	0.976 (19)	2.612 (19)	3.579 (2)	170.8 (16)
C6—H6···N2ii	0.969 (17)	2.515 (17)	3.469 (2)	167.8 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N3i	0.976 (19)	2.612 (19)	3.579 (2)	170.8 (16)
C6—H6⋯N2ii	0.969 (17)	2.515 (17)	3.469 (2)	167.8 (14)

Symmetry codes: (i) ; (ii) .