2,5-Dimethyl-N-[1-(1H-pyrrol-2-yl)ethyl-idene]aniline.

In the title compound, C(14)H(16)N(2), the pyrrole and benzene rings form a dihedral angle of 72.37 (8)°. In the crystal, centrosymmetrically related mol-ecules are assembled into dimers by by pairs of N-H⋯N hydrogen bonds, generating rings of R(2) (2)(10) graph-set motif. C-H⋯π inter-actions also occur.

Related literature

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

Experimental

Crystal data

C14H16N2

M = 212.29

Monoclinic,

a = 12.5894 (17) Å

b = 7.3109 (10) Å

c = 14.8425 (19) Å

β = 113.118 (2)°

V = 1256.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.37 × 0.28 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.976, T max = 0.990

6463 measured reflections

2441 independent reflections

1885 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.156

S = 0.96

2441 reflections

149 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.16 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040858/rz5010sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040858/rz5010Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812040858/rz5010Isup3.cml

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

C14H16N2	F(000) = 456
Mr = 212.29	Dx = 1.122 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2093 reflections
a = 12.5894 (17) Å	θ = 2.7–26.0°
b = 7.3109 (10) Å	µ = 0.07 mm−1
c = 14.8425 (19) Å	T = 296 K
β = 113.118 (2)°	Block, colourless
V = 1256.4 (3) Å3	0.37 × 0.28 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	2441 independent reflections
Radiation source: fine-focus sealed tube	1885 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→13
Tmin = 0.976, Tmax = 0.990	k = −8→8
6463 measured reflections	l = −18→15

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.1P)2 + 0.1684P] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.001
2441 reflections	Δρmax = 0.22 e Å−3
149 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (5)

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	0.02765 (11)	0.93936 (18)	0.15136 (9)	0.0509 (4)
H1	−0.0111	0.9621	0.0903	0.061*
N2	0.16704 (11)	0.92217 (17)	0.04350 (9)	0.0493 (4)
C1	−0.01726 (14)	0.9302 (2)	0.22049 (12)	0.0556 (5)
H1A	−0.0944	0.9481	0.2098	0.067*
C2	0.06832 (16)	0.8908 (2)	0.30727 (13)	0.0606 (5)
H2	0.0608	0.8759	0.3667	0.073*
C3	0.17118 (15)	0.8764 (2)	0.29152 (12)	0.0572 (5)
H3	0.2441	0.8510	0.3388	0.069*
C4	0.14446 (13)	0.90679 (19)	0.19355 (11)	0.0447 (4)
C5	0.21617 (12)	0.90262 (18)	0.13711 (11)	0.0429 (4)
C6	0.34366 (13)	0.8754 (3)	0.19343 (12)	0.0584 (5)
H6A	0.3790	0.8420	0.1491	0.088*
H6B	0.3559	0.7799	0.2409	0.088*
H6C	0.3774	0.9870	0.2263	0.088*
C7	0.23363 (12)	0.9170 (2)	−0.01501 (11)	0.0463 (4)
C8	0.29383 (12)	1.0713 (2)	−0.02269 (11)	0.0495 (4)
H8	0.2956	1.1732	0.0154	0.059*
C9	0.35159 (13)	1.0782 (2)	−0.08547 (12)	0.0519 (4)
C10	0.34733 (15)	0.9243 (2)	−0.14132 (12)	0.0593 (5)
H10	0.3852	0.9247	−0.1840	0.071*
C11	0.28748 (15)	0.7705 (2)	−0.13432 (12)	0.0596 (5)
H11	0.2865	0.6689	−0.1723	0.072*
C12	0.22837 (14)	0.7620 (2)	−0.07228 (11)	0.0519 (4)
C13	0.41634 (15)	1.2478 (3)	−0.09201 (14)	0.0697 (6)
H13A	0.4961	1.2359	−0.0489	0.105*
H13B	0.3837	1.3525	−0.0733	0.105*
H13C	0.4104	1.2630	−0.1581	0.105*
C14	0.16000 (19)	0.5964 (3)	−0.06737 (16)	0.0763 (6)
H14A	0.1561	0.5120	−0.1181	0.115*
H14B	0.0833	0.6330	−0.0762	0.115*
H14C	0.1969	0.5386	−0.0047	0.115*

	U11	U22	U33	U12	U13	U23
N1	0.0432 (7)	0.0719 (9)	0.0400 (7)	0.0059 (6)	0.0191 (6)	0.0070 (6)
N2	0.0423 (7)	0.0664 (9)	0.0424 (7)	0.0002 (6)	0.0202 (6)	−0.0022 (6)
C1	0.0489 (9)	0.0738 (11)	0.0523 (10)	0.0075 (8)	0.0288 (8)	0.0091 (8)
C2	0.0652 (10)	0.0790 (12)	0.0473 (9)	0.0149 (9)	0.0326 (8)	0.0163 (8)
C3	0.0541 (9)	0.0734 (11)	0.0453 (9)	0.0149 (8)	0.0209 (7)	0.0138 (8)
C4	0.0438 (8)	0.0480 (8)	0.0448 (8)	0.0050 (6)	0.0201 (7)	0.0048 (6)
C5	0.0433 (8)	0.0435 (8)	0.0443 (8)	0.0028 (6)	0.0199 (7)	0.0018 (6)
C6	0.0464 (9)	0.0780 (11)	0.0532 (10)	0.0155 (8)	0.0224 (8)	0.0126 (8)
C7	0.0386 (7)	0.0633 (10)	0.0379 (8)	0.0077 (6)	0.0160 (6)	0.0014 (6)
C8	0.0434 (8)	0.0631 (10)	0.0434 (9)	0.0018 (7)	0.0186 (7)	−0.0037 (7)
C9	0.0407 (8)	0.0717 (11)	0.0447 (9)	0.0111 (7)	0.0182 (7)	0.0096 (7)
C10	0.0574 (10)	0.0814 (13)	0.0470 (9)	0.0206 (9)	0.0290 (8)	0.0107 (8)
C11	0.0686 (11)	0.0677 (11)	0.0442 (9)	0.0206 (9)	0.0240 (8)	−0.0019 (7)
C12	0.0515 (9)	0.0592 (10)	0.0417 (8)	0.0093 (7)	0.0146 (7)	0.0018 (7)
C13	0.0578 (10)	0.0887 (14)	0.0699 (12)	−0.0006 (9)	0.0330 (9)	0.0152 (10)
C14	0.0877 (14)	0.0680 (13)	0.0735 (14)	−0.0043 (10)	0.0318 (12)	−0.0063 (9)

N1—C1	1.3536 (19)	C7—C12	1.403 (2)
N1—C4	1.3742 (19)	C8—C9	1.390 (2)
N1—H1	0.8600	C8—H8	0.9300
N2—C5	1.288 (2)	C9—C10	1.386 (2)
N2—C7	1.4248 (18)	C9—C13	1.508 (2)
C1—C2	1.346 (2)	C10—C11	1.380 (2)
C1—H1A	0.9300	C10—H10	0.9300
C2—C3	1.407 (2)	C11—C12	1.394 (2)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.376 (2)	C12—C14	1.504 (2)
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.453 (2)	C13—H13B	0.9600
C5—C6	1.504 (2)	C13—H13C	0.9600
C6—H6A	0.9600	C14—H14A	0.9600
C6—H6B	0.9600	C14—H14B	0.9600
C6—H6C	0.9600	C14—H14C	0.9600
C7—C8	1.388 (2)
C1—N1—C4	109.68 (13)	C7—C8—C9	122.06 (14)
C1—N1—H1	125.2	C7—C8—H8	119.0
C4—N1—H1	125.2	C9—C8—H8	119.0
C5—N2—C7	120.42 (13)	C10—C9—C8	117.65 (15)
C2—C1—N1	108.68 (14)	C10—C9—C13	121.59 (15)
C2—C1—H1A	125.7	C8—C9—C13	120.75 (15)
N1—C1—H1A	125.7	C11—C10—C9	120.68 (15)
C1—C2—C3	107.46 (15)	C11—C10—H10	119.7
C1—C2—H2	126.3	C9—C10—H10	119.7
C3—C2—H2	126.3	C10—C11—C12	122.33 (15)
C4—C3—C2	107.72 (15)	C10—C11—H11	118.8
C4—C3—H3	126.1	C12—C11—H11	118.8
C2—C3—H3	126.1	C11—C12—C7	117.00 (15)
N1—C4—C3	106.46 (13)	C11—C12—C14	122.13 (15)
N1—C4—C5	122.47 (13)	C7—C12—C14	120.86 (14)
C3—C4—C5	131.04 (14)	C9—C13—H13A	109.5
N2—C5—C4	118.40 (13)	C9—C13—H13B	109.5
N2—C5—C6	124.76 (13)	H13A—C13—H13B	109.5
C4—C5—C6	116.83 (13)	C9—C13—H13C	109.5
C5—C6—H6A	109.5	H13A—C13—H13C	109.5
C5—C6—H6B	109.5	H13B—C13—H13C	109.5
H6A—C6—H6B	109.5	C12—C14—H14A	109.5
C5—C6—H6C	109.5	C12—C14—H14B	109.5
H6A—C6—H6C	109.5	H14A—C14—H14B	109.5
H6B—C6—H6C	109.5	C12—C14—H14C	109.5
C8—C7—C12	120.27 (14)	H14A—C14—H14C	109.5
C8—C7—N2	119.97 (13)	H14B—C14—H14C	109.5
C12—C7—N2	119.44 (13)
C4—N1—C1—C2	−0.40 (19)	C5—N2—C7—C12	105.74 (16)
N1—C1—C2—C3	0.5 (2)	C12—C7—C8—C9	−0.7 (2)
C1—C2—C3—C4	−0.4 (2)	N2—C7—C8—C9	−174.23 (13)
C1—N1—C4—C3	0.13 (17)	C7—C8—C9—C10	0.1 (2)
C1—N1—C4—C5	178.29 (13)	C7—C8—C9—C13	−179.93 (15)
C2—C3—C4—N1	0.17 (18)	C8—C9—C10—C11	0.1 (2)
C2—C3—C4—C5	−177.76 (15)	C13—C9—C10—C11	−179.93 (15)
C7—N2—C5—C4	−179.32 (12)	C9—C10—C11—C12	0.5 (3)
C7—N2—C5—C6	0.7 (2)	C10—C11—C12—C7	−1.1 (2)
N1—C4—C5—N2	−3.2 (2)	C10—C11—C12—C14	177.92 (16)
C3—C4—C5—N2	174.48 (16)	C8—C7—C12—C11	1.2 (2)
N1—C4—C5—C6	176.84 (14)	N2—C7—C12—C11	174.73 (13)
C3—C4—C5—C6	−5.5 (2)	C8—C7—C12—C14	−177.81 (15)
C5—N2—C7—C8	−80.71 (18)	N2—C7—C12—C14	−4.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.86	2.34	3.1354 (18)	155
C1—H1A···Cg1i	0.93	2.65	3.4298 (16)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.86	2.34	3.1354 (18)	155
C1—H1A⋯Cg1i	0.93	2.65	3.4298 (16)	142

Symmetry code: (i) .