2,3-Dimethyl-N-[(E)-(1H-pyrrol-2-yl)methyl-idene]aniline.

In the title compound, C(13)H(14)N(2), the dihedral angle between the aromatic rings is 69.73 (14)°. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds generate R(2) (2)(10) loops. A weak C-H⋯π inter-action also occurs.

Related literature

For background to Schiff bases and for related structures, see: Hussain et al. (2010a ▶,b ▶), Sarfraz et al. (2010 ▶); Tariq et al. (2010 ▶): For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H14N2

M = 198.26

Monoclinic,

a = 12.8684 (9) Å

b = 7.1649 (5) Å

c = 12.9517 (9) Å

β = 107.613 (3)°

V = 1138.18 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.30 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.980, T max = 0.993

8641 measured reflections

2066 independent reflections

1075 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.142

S = 1.01

2066 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.13 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: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031867/hb5606sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031867/hb5606Isup2.hkl

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

C13H14N2	F(000) = 424
Mr = 198.26	Dx = 1.157 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1075 reflections
a = 12.8684 (9) Å	θ = 3.2–25.3°
b = 7.1649 (5) Å	µ = 0.07 mm−1
c = 12.9517 (9) Å	T = 296 K
β = 107.613 (3)°	Needle, colourless
V = 1138.18 (14) Å3	0.30 × 0.12 × 0.10 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2066 independent reflections
Radiation source: fine-focus sealed tube	1075 reflections with I > 2σ(I)
graphite	Rint = 0.065
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 3.2°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
Tmin = 0.980, Tmax = 0.993	l = −15→15
8641 measured reflections

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0559P)2 + 0.0942P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2066 reflections	Δρmax = 0.15 e Å−3
139 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: 0.019 (4)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.39549 (16)	0.8356 (3)	0.05111 (16)	0.0532 (8)
N2	0.62151 (16)	0.9535 (3)	0.15496 (16)	0.0550 (8)
C1	0.2837 (2)	0.7796 (3)	0.01500 (19)	0.0499 (9)
C2	0.25093 (19)	0.6419 (4)	−0.06368 (19)	0.0539 (9)
C3	0.1406 (2)	0.5922 (4)	−0.1006 (2)	0.0659 (11)
C4	0.0680 (2)	0.6814 (4)	−0.0579 (3)	0.0787 (11)
C5	0.1015 (2)	0.8157 (4)	0.0209 (3)	0.0834 (14)
C6	0.2096 (2)	0.8668 (4)	0.0569 (2)	0.0675 (11)
C7	0.3339 (2)	0.5434 (4)	−0.1043 (2)	0.0766 (11)
C8	0.0995 (3)	0.4408 (5)	−0.1836 (2)	0.1085 (16)
C9	0.44692 (19)	0.8048 (3)	0.1505 (2)	0.0516 (9)
C10	0.55763 (19)	0.8560 (3)	0.20329 (18)	0.0495 (9)
C11	0.6209 (2)	0.8162 (3)	0.3068 (2)	0.0592 (10)
C12	0.7242 (2)	0.8895 (4)	0.3205 (2)	0.0642 (10)
C13	0.7225 (2)	0.9738 (4)	0.2261 (2)	0.0635 (10)
H2	0.60086	0.99538	0.08967	0.0660*
H4	−0.00546	0.64985	−0.08297	0.0945*
H5	0.05137	0.87191	0.04976	0.1003*
H6	0.23263	0.95956	0.10904	0.0810*
H7A	0.39874	0.61809	−0.08930	0.1147*
H7B	0.30476	0.52419	−0.18105	0.1147*
H7C	0.35134	0.42497	−0.06860	0.1147*
H8A	0.13149	0.32366	−0.15456	0.1628*
H8B	0.11924	0.46977	−0.24760	0.1628*
H8C	0.02160	0.43251	−0.20160	0.1628*
H9	0.40938	0.74430	0.19188	0.0620*
H11	0.59856	0.75163	0.35870	0.0711*
H12	0.78356	0.88212	0.38276	0.0770*
H13	0.78071	1.03508	0.21258	0.0763*

	U11	U22	U33	U12	U13	U23
N1	0.0534 (13)	0.0565 (14)	0.0494 (13)	−0.0073 (10)	0.0151 (10)	−0.0022 (10)
N2	0.0577 (14)	0.0540 (13)	0.0507 (12)	−0.0053 (11)	0.0125 (11)	0.0011 (11)
C1	0.0516 (16)	0.0490 (15)	0.0490 (14)	−0.0008 (12)	0.0153 (12)	0.0051 (13)
C2	0.0564 (17)	0.0560 (17)	0.0510 (15)	−0.0043 (13)	0.0186 (13)	0.0053 (13)
C3	0.0591 (19)	0.072 (2)	0.0619 (18)	−0.0102 (15)	0.0113 (15)	0.0075 (15)
C4	0.0465 (17)	0.093 (2)	0.088 (2)	−0.0013 (17)	0.0074 (16)	0.019 (2)
C5	0.062 (2)	0.087 (2)	0.107 (3)	0.0197 (18)	0.0343 (19)	0.009 (2)
C6	0.0686 (19)	0.0597 (18)	0.0789 (19)	0.0044 (15)	0.0294 (16)	−0.0047 (15)
C7	0.081 (2)	0.078 (2)	0.0773 (19)	−0.0120 (16)	0.0337 (16)	−0.0202 (17)
C8	0.096 (3)	0.131 (3)	0.091 (2)	−0.048 (2)	0.017 (2)	−0.027 (2)
C9	0.0581 (16)	0.0438 (16)	0.0572 (16)	−0.0029 (12)	0.0238 (13)	−0.0030 (13)
C10	0.0542 (15)	0.0424 (15)	0.0523 (16)	−0.0024 (12)	0.0166 (13)	−0.0010 (12)
C11	0.0691 (18)	0.0551 (17)	0.0535 (16)	0.0032 (14)	0.0185 (14)	0.0019 (13)
C12	0.0635 (19)	0.0616 (18)	0.0590 (17)	0.0050 (14)	0.0056 (14)	−0.0032 (15)
C13	0.0525 (17)	0.0635 (18)	0.0692 (18)	−0.0074 (14)	0.0103 (14)	−0.0044 (16)

N1—C1	1.429 (3)	C11—C12	1.390 (4)
N1—C9	1.276 (3)	C12—C13	1.358 (4)
N2—C10	1.366 (3)	C4—H4	0.9300
N2—C13	1.354 (3)	C5—H5	0.9300
N2—H2	0.8600	C6—H6	0.9300
C1—C2	1.389 (3)	C7—H7A	0.9600
C1—C6	1.381 (4)	C7—H7B	0.9600
C2—C7	1.502 (4)	C7—H7C	0.9600
C2—C3	1.400 (4)	C8—H8A	0.9600
C3—C4	1.378 (4)	C8—H8B	0.9600
C3—C8	1.506 (4)	C8—H8C	0.9600
C4—C5	1.374 (5)	C9—H9	0.9300
C5—C6	1.376 (4)	C11—H11	0.9300
C9—C10	1.429 (4)	C12—H12	0.9300
C10—C11	1.372 (3)	C13—H13	0.9300
C1—N1—C9	116.4 (2)	C4—C5—H5	120.00
C10—N2—C13	109.3 (2)	C6—C5—H5	120.00
C10—N2—H2	125.00	C1—C6—H6	120.00
C13—N2—H2	125.00	C5—C6—H6	120.00
N1—C1—C2	119.5 (2)	C2—C7—H7A	109.00
N1—C1—C6	119.4 (2)	C2—C7—H7B	109.00
C2—C1—C6	121.1 (2)	C2—C7—H7C	110.00
C1—C2—C3	118.9 (2)	H7A—C7—H7B	109.00
C3—C2—C7	121.1 (2)	H7A—C7—H7C	109.00
C1—C2—C7	120.0 (2)	H7B—C7—H7C	109.00
C2—C3—C8	121.9 (3)	C3—C8—H8A	109.00
C4—C3—C8	119.1 (3)	C3—C8—H8B	109.00
C2—C3—C4	119.0 (3)	C3—C8—H8C	109.00
C3—C4—C5	121.6 (3)	H8A—C8—H8B	109.00
C4—C5—C6	119.7 (3)	H8A—C8—H8C	109.00
C1—C6—C5	119.6 (3)	H8B—C8—H8C	109.00
N1—C9—C10	125.2 (2)	N1—C9—H9	117.00
N2—C10—C11	107.0 (2)	C10—C9—H9	117.00
C9—C10—C11	128.7 (2)	C10—C11—H11	126.00
N2—C10—C9	124.3 (2)	C12—C11—H11	126.00
C10—C11—C12	108.0 (2)	C11—C12—H12	126.00
C11—C12—C13	107.4 (2)	C13—C12—H12	126.00
N2—C13—C12	108.4 (2)	N2—C13—H13	126.00
C3—C4—H4	119.00	C12—C13—H13	126.00
C5—C4—H4	119.00
C9—N1—C1—C2	−116.5 (3)	C1—C2—C3—C8	−178.4 (2)
C9—N1—C1—C6	65.2 (3)	C7—C2—C3—C4	177.5 (3)
C1—N1—C9—C10	−177.7 (2)	C7—C2—C3—C8	−1.0 (4)
C13—N2—C10—C9	−178.2 (2)	C2—C3—C4—C5	−0.9 (5)
C13—N2—C10—C11	0.3 (3)	C8—C3—C4—C5	177.6 (3)
C10—N2—C13—C12	0.0 (3)	C3—C4—C5—C6	1.6 (5)
N1—C1—C2—C3	−178.2 (2)	C4—C5—C6—C1	−1.4 (4)
N1—C1—C2—C7	4.4 (4)	N1—C9—C10—N2	3.4 (4)
C6—C1—C2—C3	0.1 (4)	N1—C9—C10—C11	−174.7 (2)
C6—C1—C2—C7	−177.3 (2)	N2—C10—C11—C12	−0.4 (3)
N1—C1—C6—C5	178.8 (2)	C9—C10—C11—C12	177.9 (2)
C2—C1—C6—C5	0.5 (4)	C10—C11—C12—C13	0.5 (3)
C1—C2—C3—C4	0.1 (4)	C11—C12—C13—N2	−0.3 (3)

Cg1 is the centroid of the C10–C13/N2 pyrrol ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.86	2.20	3.017 (3)	158
C9—H9···Cg1ii	0.93	2.80	3.606 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C13/N2 pyrrol ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.86	2.20	3.017 (3)	158
C9—H9⋯Cg1ii	0.93	2.80	3.606 (3)	145

Symmetry codes: (i) ; (ii) .