N-[1-(1H-Pyrrol-2-yl)ethyl-idene]aniline.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(12)H(12)N(2), in which the pyrrole and benzene rings form dihedral angles of 72.37 (7) and 82.34 (8)°. The imino N-C bond lengths in the two mol-ecules are equal [1.286 (2) Å] and indicate C=N character. In the crystal, each mol-ecule forms a dimer with an inversion-related mol-ecule through a pair of classical N-H⋯N hydrogen bonds.

Related literature

For general background to the imino­pyrrole unit, see: Small et al. (1998 ▶); Su et al. (2009a ▶,b ▶); Britovsek et al. (2003 ▶); Dawson et al. (2000 ▶). For the pyrrole diimine unit, see: Matsuo et al. (2001 ▶) and for the pyrrole monoimine unit, see: He et al. (2009 ▶).

Experimental

Crystal data

C12H12N2

M = 184.24

Triclinic,

a = 8.2236 (14) Å

b = 11.3306 (19) Å

c = 11.913 (2) Å

α = 95.984 (3)°

β = 93.202 (3)°

γ = 109.274 (3)°

V = 1037.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.37 × 0.25 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.974, T max = 0.987

5277 measured reflections

3655 independent reflections

2567 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.142

S = 1.10

3655 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker,2008 ▶); cell refinement: SAINT (Bruker,2008 ▶); data reduction: SAINT; 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037695/rk2378sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037695/rk2378Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037695/rk2378Isup3.cml

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

C12H12N2	Z = 4
Mr = 184.24	F(000) = 392
Triclinic, P1	Dx = 1.180 Mg m−3
Hall symbol: -P 1	Melting point = 405.25–406.85 K
a = 8.2236 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3306 (19) Å	Cell parameters from 1351 reflections
c = 11.913 (2) Å	θ = 2.4–25.1°
α = 95.984 (3)°	µ = 0.07 mm−1
β = 93.202 (3)°	T = 296 K
γ = 109.274 (3)°	Block, colourless
V = 1037.3 (3) Å3	0.37 × 0.25 × 0.19 mm

Bruker APEXII CCD diffractometer	3655 independent reflections
Radiation source: fine-focus sealed tube	2567 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.974, Tmax = 0.987	k = −9→13
5277 measured reflections	l = −14→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0689P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
3655 reflections	Δρmax = 0.20 e Å−3
256 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (5)

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 > 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	0.1204 (2)	1.17200 (13)	0.61426 (13)	0.0613 (4)
H1A	0.0627	1.1263	0.5534	0.074*
N2	0.19520 (19)	0.94813 (13)	0.57233 (12)	0.0557 (4)
N3	0.38995 (19)	0.64751 (14)	−0.01282 (12)	0.0557 (4)
H3A	0.4486	0.6007	−0.0354	0.067*
N4	0.31361 (19)	0.43111 (14)	0.10218 (13)	0.0569 (4)
C1	0.1184 (3)	1.28776 (18)	0.6531 (2)	0.0780 (6)
H1	0.0539	1.3305	0.6192	0.094*
C2	0.2261 (3)	1.3311 (2)	0.7498 (2)	0.0812 (7)
H2	0.2502	1.4089	0.7935	0.097*
C3	0.2940 (3)	1.23792 (19)	0.77152 (17)	0.0699 (6)
H3	0.3710	1.2419	0.8332	0.084*
C4	0.2279 (2)	1.13853 (16)	0.68614 (15)	0.0524 (5)
C5	0.2640 (2)	1.02211 (16)	0.66444 (14)	0.0519 (5)
C6	0.3844 (3)	0.9990 (2)	0.75197 (17)	0.0783 (6)
H6A	0.3216	0.9665	0.8140	0.117*
H6B	0.4757	1.0767	0.7793	0.117*
H6C	0.4331	0.9389	0.7187	0.117*
C7	0.2301 (2)	0.83354 (16)	0.54888 (15)	0.0525 (5)
C8	0.1630 (3)	0.73360 (18)	0.60871 (18)	0.0726 (6)
H8	0.0976	0.7418	0.6684	0.087*
C9	0.1917 (3)	0.62193 (19)	0.5811 (2)	0.0814 (7)
H9	0.1457	0.5553	0.6224	0.098*
C10	0.2873 (3)	0.6075 (2)	0.4936 (2)	0.0781 (6)
H10	0.3072	0.5319	0.4756	0.094*
C11	0.3536 (3)	0.7066 (2)	0.43257 (19)	0.0772 (6)
H11	0.4184	0.6980	0.3727	0.093*
C12	0.3241 (3)	0.81884 (18)	0.46002 (17)	0.0664 (5)
H12	0.3683	0.8850	0.4179	0.080*
C13	0.4041 (3)	0.76033 (19)	−0.04693 (17)	0.0651 (5)
H13	0.4783	0.8000	−0.0982	0.078*
C14	0.2908 (3)	0.8061 (2)	0.00674 (18)	0.0698 (6)
H14	0.2736	0.8820	−0.0013	0.084*
C15	0.2060 (3)	0.71803 (18)	0.07579 (17)	0.0627 (5)
H15	0.1218	0.7249	0.1225	0.075*
C16	0.2679 (2)	0.61897 (16)	0.06320 (14)	0.0507 (4)
C17	0.2239 (2)	0.50444 (16)	0.11674 (14)	0.0503 (4)
C18	0.0726 (3)	0.47986 (18)	0.18618 (16)	0.0656 (5)
H18A	−0.0259	0.4157	0.1446	0.098*
H18B	0.0462	0.5560	0.2025	0.098*
H18C	0.1006	0.4522	0.2559	0.098*
C19	0.2680 (2)	0.31984 (17)	0.15675 (16)	0.0561 (5)
C20	0.3454 (3)	0.3213 (2)	0.26340 (17)	0.0708 (6)
H20	0.4238	0.3961	0.3014	0.085*
C21	0.3063 (3)	0.2120 (3)	0.3132 (2)	0.0850 (7)
H21	0.3581	0.2136	0.3851	0.102*
C22	0.1926 (3)	0.1014 (2)	0.2583 (2)	0.0873 (7)
H22	0.1663	0.0283	0.2927	0.105*
C23	0.1175 (3)	0.0987 (2)	0.1524 (2)	0.0869 (7)
H23	0.0404	0.0233	0.1147	0.104*
C24	0.1551 (3)	0.2071 (2)	0.10094 (19)	0.0730 (6)
H24	0.1042	0.2042	0.0285	0.088*

	U11	U22	U33	U12	U13	U23
N1	0.0669 (10)	0.0474 (9)	0.0668 (10)	0.0195 (8)	−0.0074 (8)	0.0011 (7)
N2	0.0601 (9)	0.0484 (8)	0.0593 (9)	0.0191 (7)	0.0030 (8)	0.0102 (7)
N3	0.0549 (9)	0.0621 (10)	0.0579 (9)	0.0271 (7)	0.0110 (7)	0.0155 (7)
N4	0.0530 (9)	0.0618 (9)	0.0627 (9)	0.0236 (8)	0.0156 (7)	0.0197 (7)
C1	0.0800 (15)	0.0517 (12)	0.1002 (17)	0.0274 (11)	−0.0127 (13)	−0.0059 (11)
C2	0.0714 (14)	0.0616 (13)	0.1009 (17)	0.0213 (11)	−0.0030 (13)	−0.0218 (12)
C3	0.0603 (12)	0.0749 (14)	0.0679 (13)	0.0209 (11)	−0.0028 (10)	−0.0087 (11)
C4	0.0485 (10)	0.0518 (10)	0.0555 (11)	0.0150 (8)	0.0054 (8)	0.0070 (8)
C5	0.0497 (10)	0.0543 (11)	0.0520 (10)	0.0155 (8)	0.0071 (8)	0.0141 (9)
C6	0.0889 (16)	0.0862 (15)	0.0665 (13)	0.0400 (13)	−0.0089 (12)	0.0134 (11)
C7	0.0519 (10)	0.0509 (10)	0.0556 (10)	0.0183 (8)	0.0031 (8)	0.0092 (8)
C8	0.0878 (15)	0.0604 (12)	0.0798 (14)	0.0309 (11)	0.0335 (12)	0.0210 (10)
C9	0.1039 (18)	0.0574 (13)	0.0943 (16)	0.0343 (12)	0.0340 (14)	0.0233 (11)
C10	0.0847 (16)	0.0590 (13)	0.0935 (16)	0.0301 (12)	0.0134 (13)	0.0005 (12)
C11	0.0715 (14)	0.0779 (15)	0.0800 (15)	0.0235 (12)	0.0208 (12)	−0.0006 (12)
C12	0.0682 (13)	0.0598 (12)	0.0673 (13)	0.0145 (10)	0.0140 (10)	0.0109 (10)
C13	0.0620 (12)	0.0718 (13)	0.0703 (13)	0.0282 (10)	0.0107 (10)	0.0277 (10)
C14	0.0744 (14)	0.0705 (13)	0.0780 (14)	0.0382 (11)	0.0132 (11)	0.0213 (11)
C15	0.0641 (12)	0.0711 (13)	0.0634 (12)	0.0339 (10)	0.0145 (10)	0.0142 (10)
C16	0.0457 (10)	0.0615 (11)	0.0473 (10)	0.0208 (8)	0.0051 (8)	0.0084 (8)
C17	0.0472 (10)	0.0583 (11)	0.0457 (10)	0.0188 (8)	0.0033 (8)	0.0055 (8)
C18	0.0647 (12)	0.0725 (13)	0.0672 (12)	0.0293 (10)	0.0216 (10)	0.0146 (10)
C19	0.0474 (10)	0.0639 (12)	0.0649 (12)	0.0248 (9)	0.0165 (9)	0.0176 (9)
C20	0.0742 (14)	0.0770 (14)	0.0659 (13)	0.0280 (11)	0.0095 (11)	0.0200 (11)
C21	0.0857 (17)	0.1045 (19)	0.0803 (15)	0.0435 (15)	0.0171 (13)	0.0376 (14)
C22	0.0747 (16)	0.0889 (18)	0.118 (2)	0.0381 (14)	0.0315 (15)	0.0529 (16)
C23	0.0701 (15)	0.0685 (14)	0.121 (2)	0.0177 (11)	0.0122 (14)	0.0271 (14)
C24	0.0618 (13)	0.0717 (14)	0.0846 (15)	0.0196 (11)	0.0001 (11)	0.0195 (11)

N1—C1	1.350 (2)	C10—C11	1.378 (3)
N1—C4	1.365 (2)	C10—H10	0.9300
N1—H1A	0.8600	C11—C12	1.381 (3)
N2—C5	1.286 (2)	C11—H11	0.9300
N2—C7	1.423 (2)	C12—H12	0.9300
N3—C13	1.352 (2)	C13—C14	1.364 (3)
N3—C16	1.371 (2)	C13—H13	0.9300
N3—H3A	0.8600	C14—C15	1.391 (3)
N4—C17	1.286 (2)	C14—H14	0.9300
N4—C19	1.428 (2)	C15—C16	1.376 (2)
C1—C2	1.355 (3)	C15—H15	0.9300
C1—H1	0.9300	C16—C17	1.453 (2)
C2—C3	1.387 (3)	C17—C18	1.498 (2)
C2—H2	0.9300	C18—H18A	0.9600
C3—C4	1.376 (2)	C18—H18B	0.9600
C3—H3	0.9300	C18—H18C	0.9600
C4—C5	1.446 (2)	C19—C24	1.381 (3)
C5—C6	1.500 (3)	C19—C20	1.385 (3)
C6—H6A	0.9600	C20—C21	1.379 (3)
C6—H6B	0.9600	C20—H20	0.9300
C6—H6C	0.9600	C21—C22	1.363 (3)
C7—C12	1.373 (3)	C21—H21	0.9300
C7—C8	1.376 (3)	C22—C23	1.366 (3)
C8—C9	1.373 (3)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.381 (3)
C9—C10	1.368 (3)	C23—H23	0.9300
C9—H9	0.9300	C24—H24	0.9300
C1—N1—C4	109.71 (17)	C12—C11—H11	119.9
C1—N1—H1A	125.1	C7—C12—C11	120.60 (19)
C4—N1—H1A	125.1	C7—C12—H12	119.7
C5—N2—C7	119.64 (15)	C11—C12—H12	119.7
C13—N3—C16	109.70 (15)	N3—C13—C14	108.30 (18)
C13—N3—H3A	125.2	N3—C13—H13	125.9
C16—N3—H3A	125.2	C14—C13—H13	125.9
C17—N4—C19	118.11 (15)	C13—C14—C15	107.20 (18)
N1—C1—C2	108.44 (19)	C13—C14—H14	126.4
N1—C1—H1	125.8	C15—C14—H14	126.4
C2—C1—H1	125.8	C16—C15—C14	108.33 (17)
C1—C2—C3	107.24 (18)	C16—C15—H15	125.8
C1—C2—H2	126.4	C14—C15—H15	125.8
C3—C2—H2	126.4	N3—C16—C15	106.47 (15)
C4—C3—C2	108.29 (18)	N3—C16—C17	123.18 (15)
C4—C3—H3	125.9	C15—C16—C17	130.35 (16)
C2—C3—H3	125.9	N4—C17—C16	119.49 (16)
N1—C4—C3	106.31 (16)	N4—C17—C18	124.21 (16)
N1—C4—C5	122.82 (16)	C16—C17—C18	116.31 (15)
C3—C4—C5	130.76 (18)	C17—C18—H18A	109.5
N2—C5—C4	118.71 (16)	C17—C18—H18B	109.5
N2—C5—C6	124.98 (17)	H18A—C18—H18B	109.5
C4—C5—C6	116.29 (16)	C17—C18—H18C	109.5
C5—C6—H6A	109.5	H18A—C18—H18C	109.5
C5—C6—H6B	109.5	H18B—C18—H18C	109.5
H6A—C6—H6B	109.5	C24—C19—C20	118.90 (19)
C5—C6—H6C	109.5	C24—C19—N4	120.50 (18)
H6A—C6—H6C	109.5	C20—C19—N4	120.46 (17)
H6B—C6—H6C	109.5	C21—C20—C19	120.0 (2)
C12—C7—C8	118.78 (17)	C21—C20—H20	120.0
C12—C7—N2	119.48 (16)	C19—C20—H20	120.0
C8—C7—N2	121.62 (17)	C22—C21—C20	120.7 (2)
C9—C8—C7	120.61 (19)	C22—C21—H21	119.6
C9—C8—H8	119.7	C20—C21—H21	119.6
C7—C8—H8	119.7	C23—C22—C21	119.7 (2)
C10—C9—C8	120.8 (2)	C23—C22—H22	120.2
C10—C9—H9	119.6	C21—C22—H22	120.2
C8—C9—H9	119.6	C22—C23—C24	120.5 (2)
C9—C10—C11	119.0 (2)	C22—C23—H23	119.7
C9—C10—H10	120.5	C24—C23—H23	119.7
C11—C10—H10	120.5	C19—C24—C23	120.2 (2)
C10—C11—C12	120.2 (2)	C19—C24—H24	119.9
C10—C11—H11	119.9	C23—C24—H24	119.9
C4—N1—C1—C2	0.7 (2)	C16—N3—C13—C14	−0.1 (2)
N1—C1—C2—C3	−0.9 (3)	N3—C13—C14—C15	0.2 (2)
C1—C2—C3—C4	0.8 (2)	C13—C14—C15—C16	−0.2 (2)
C1—N1—C4—C3	−0.2 (2)	C13—N3—C16—C15	−0.1 (2)
C1—N1—C4—C5	−176.80 (17)	C13—N3—C16—C17	−179.24 (16)
C2—C3—C4—N1	−0.3 (2)	C14—C15—C16—N3	0.2 (2)
C2—C3—C4—C5	175.84 (19)	C14—C15—C16—C17	179.27 (18)
C7—N2—C5—C4	179.53 (15)	C19—N4—C17—C16	179.47 (15)
C7—N2—C5—C6	1.0 (3)	C19—N4—C17—C18	−0.9 (3)
N1—C4—C5—N2	1.6 (3)	N3—C16—C17—N4	7.2 (3)
C3—C4—C5—N2	−174.05 (19)	C15—C16—C17—N4	−171.75 (18)
N1—C4—C5—C6	−179.77 (17)	N3—C16—C17—C18	−172.52 (16)
C3—C4—C5—C6	4.6 (3)	C15—C16—C17—C18	8.6 (3)
C5—N2—C7—C12	−112.9 (2)	C17—N4—C19—C24	92.6 (2)
C5—N2—C7—C8	71.2 (2)	C17—N4—C19—C20	−91.9 (2)
C12—C7—C8—C9	1.0 (3)	C24—C19—C20—C21	−1.4 (3)
N2—C7—C8—C9	176.9 (2)	N4—C19—C20—C21	−177.05 (18)
C7—C8—C9—C10	−0.1 (4)	C19—C20—C21—C22	0.4 (3)
C8—C9—C10—C11	−0.5 (4)	C20—C21—C22—C23	0.5 (4)
C9—C10—C11—C12	0.2 (3)	C21—C22—C23—C24	−0.4 (4)
C8—C7—C12—C11	−1.2 (3)	C20—C19—C24—C23	1.5 (3)
N2—C7—C12—C11	−177.28 (17)	N4—C19—C24—C23	177.15 (18)
C10—C11—C12—C7	0.6 (3)	C22—C23—C24—C19	−0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.86	2.38	3.150 (2)	150
N3—H3A···N4ii	0.86	2.27	3.065 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.86	2.38	3.150 (2)	150
N3—H3A⋯N4ii	0.86	2.27	3.065 (2)	153

Symmetry codes: (i) ; (ii) .