(E)-2,4,6-Trimethyl-N-[(1H-pyrrol-2-yl)methyl-idene]aniline.

The title compound, C14H16N2, is a pyrrole-2-carbaldimine ligand that shows an E conformation at the imine double bond. The dihedral angle between the rings is 78.3 (1)°. In the crystal, pairs of mol-ecules form centrosymmetric dimers [graph-set descriptor is presumably R(2)2(10)] via N-H⋯N hydrogen bonds between the pyrrole N-H group and the imine N atom of a neighbouring mol-ecule.

Related literature

For structure analyses of other pyrrole-2-carbaldimines in which the substituents at the imine N atoms do not include functional groups that are capable of forming additional hydrogen bonds, see: Gomes et al. (2010 ▶); Crestani et al. (2011 ▶); Matsui et al. (2004 ▶); Wang et al. (2007 ▶); Franceschi et al. (2001 ▶); Tahir et al. (2010 ▶); Munro et al. (2006 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For graph-set description, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H16N2

M = 212.29

Monoclinic,

a = 13.6739 (10) Å

b = 7.3086 (6) Å

c = 13.3880 (11) Å

β = 111.184 (4)°

V = 1247.54 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 183 K

0.6 × 0.4 × 0.01 mm

Data collection

Nonius KappaCCD diffractometer

4714 measured reflections

2849 independent reflections

1346 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.127

S = 0.87

2849 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.26 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); 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/S160053681205057X/bt6872sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681205057X/bt6872Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681205057X/bt6872Isup3.cml

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

C14H16N2	F(000) = 456
Mr = 212.29	Dx = 1.130 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4714 reflections
a = 13.6739 (10) Å	θ = 3.1–27.5°
b = 7.3086 (6) Å	µ = 0.07 mm−1
c = 13.3880 (11) Å	T = 183 K
β = 111.184 (4)°	Plate, light yellow
V = 1247.54 (17) Å3	0.6 × 0.4 × 0.01 mm
Z = 4

Nonius KappaCCD diffractometer	1346 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
phi–scan, ω–scan	h = −17→17
4714 measured reflections	k = −8→9
2849 independent reflections	l = −17→17

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ2(Fo2) + (0.0585P)2] where P = (Fo2 + 2Fc2)/3
2849 reflections	(Δ/σ)max = 0.032
152 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.26 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	0.40090 (11)	0.0272 (2)	0.34857 (13)	0.0391 (4)
H1A	0.4178 (15)	−0.013 (3)	0.4198 (17)	0.054 (6)*
C1	0.30475 (14)	0.0020 (2)	0.27045 (15)	0.0410 (5)
H1	0.2480	−0.0638	0.2783	0.049*
C2	0.30352 (14)	0.0875 (3)	0.17859 (15)	0.0419 (5)
H2	0.2465	0.0917	0.1119	0.050*
C3	0.40204 (13)	0.1670 (2)	0.20194 (15)	0.0394 (5)
H3	0.4241	0.2353	0.1535	0.047*
C4	0.46186 (13)	0.1297 (2)	0.30736 (14)	0.0362 (4)
C5	0.56546 (13)	0.1952 (2)	0.36830 (15)	0.0383 (5)
H5	0.6014	0.2614	0.3309	0.046*
N2	0.61285 (11)	0.1715 (2)	0.46863 (12)	0.0392 (4)
C6	0.71568 (13)	0.2505 (3)	0.51684 (14)	0.0379 (5)
C7	0.80272 (14)	0.1717 (3)	0.50284 (16)	0.0499 (5)
C8	0.90023 (15)	0.2513 (3)	0.55354 (17)	0.0573 (6)
H8	0.9594	0.1983	0.5435	0.069*
C9	0.91517 (14)	0.4035 (3)	0.61769 (16)	0.0505 (5)
C10	0.82766 (14)	0.4780 (3)	0.63231 (15)	0.0460 (5)
H10	0.8361	0.5824	0.6770	0.055*
C11	0.72809 (13)	0.4035 (3)	0.58312 (14)	0.0395 (5)
C12	0.79212 (18)	0.0021 (4)	0.4355 (2)	0.0873 (9)
H12A	0.8620	−0.0459	0.4456	0.131*
H12B	0.7555	0.0328	0.3598	0.131*
H12C	0.7520	−0.0905	0.4572	0.131*
C13	1.02310 (17)	0.4870 (4)	0.6716 (2)	0.0771 (8)
H13A	1.0601	0.4888	0.6211	0.116*
H13B	1.0630	0.4138	0.7344	0.116*
H13C	1.0159	0.6123	0.6941	0.116*
C14	0.63527 (15)	0.4899 (3)	0.60012 (18)	0.0559 (6)
H14A	0.5910	0.5509	0.5340	0.084*
H14B	0.6600	0.5800	0.6581	0.084*
H14C	0.5945	0.3951	0.6193	0.084*

	U11	U22	U33	U12	U13	U23
N1	0.0332 (8)	0.0432 (9)	0.0382 (10)	−0.0029 (7)	0.0095 (8)	0.0026 (8)
C1	0.0302 (10)	0.0436 (11)	0.0455 (12)	0.0006 (8)	0.0092 (9)	0.0005 (9)
C2	0.0357 (10)	0.0418 (11)	0.0418 (12)	0.0019 (9)	0.0060 (9)	0.0000 (9)
C3	0.0393 (10)	0.0381 (10)	0.0418 (11)	0.0023 (9)	0.0159 (9)	0.0023 (9)
C4	0.0340 (10)	0.0352 (10)	0.0405 (11)	0.0001 (8)	0.0147 (9)	−0.0028 (8)
C5	0.0357 (10)	0.0370 (11)	0.0443 (12)	−0.0014 (8)	0.0170 (9)	−0.0024 (8)
N2	0.0332 (8)	0.0446 (9)	0.0385 (10)	−0.0026 (7)	0.0113 (7)	−0.0005 (7)
C6	0.0332 (10)	0.0403 (11)	0.0382 (11)	−0.0028 (8)	0.0103 (9)	0.0026 (9)
C7	0.0408 (11)	0.0517 (13)	0.0562 (13)	−0.0030 (10)	0.0164 (10)	−0.0150 (10)
C8	0.0330 (11)	0.0726 (15)	0.0652 (15)	0.0010 (10)	0.0165 (10)	−0.0113 (12)
C9	0.0353 (11)	0.0625 (14)	0.0476 (12)	−0.0104 (10)	0.0076 (10)	−0.0065 (11)
C10	0.0437 (12)	0.0471 (12)	0.0424 (12)	−0.0065 (9)	0.0098 (9)	−0.0059 (9)
C11	0.0384 (10)	0.0433 (11)	0.0362 (11)	0.0006 (9)	0.0126 (9)	0.0008 (9)
C12	0.0499 (14)	0.0880 (19)	0.117 (2)	0.0022 (13)	0.0213 (15)	−0.0536 (17)
C13	0.0420 (12)	0.0964 (19)	0.0839 (18)	−0.0194 (13)	0.0121 (12)	−0.0216 (15)
C14	0.0458 (12)	0.0617 (13)	0.0588 (14)	0.0035 (10)	0.0172 (11)	−0.0143 (11)

N1—C1	1.365 (2)	C8—C9	1.375 (3)
N1—C4	1.376 (2)	C8—H8	0.9500
N1—H1A	0.94 (2)	C9—C10	1.391 (3)
C1—C2	1.374 (3)	C9—C13	1.517 (3)
C1—H1	0.9500	C10—C11	1.392 (2)
C2—C3	1.395 (2)	C10—H10	0.9500
C2—H2	0.9500	C11—C14	1.507 (2)
C3—C4	1.379 (2)	C12—H12A	0.9800
C3—H3	0.9500	C12—H12B	0.9800
C4—C5	1.438 (2)	C12—H12C	0.9800
C5—N2	1.275 (2)	C13—H13A	0.9800
C5—H5	0.9500	C13—H13B	0.9800
N2—C6	1.439 (2)	C13—H13C	0.9800
C6—C7	1.395 (3)	C14—H14A	0.9800
C6—C11	1.399 (3)	C14—H14B	0.9800
C7—C8	1.387 (3)	C14—H14C	0.9800
C7—C12	1.509 (3)
C1—N1—C4	108.76 (16)	C8—C9—C10	117.61 (17)
C1—N1—H1A	123.3 (12)	C8—C9—C13	121.47 (19)
C4—N1—H1A	127.7 (12)	C10—C9—C13	120.9 (2)
N1—C1—C2	108.75 (16)	C9—C10—C11	121.61 (18)
N1—C1—H1	125.6	C9—C10—H10	119.2
C2—C1—H1	125.6	C11—C10—H10	119.2
C1—C2—C3	106.88 (16)	C10—C11—C6	119.13 (16)
C1—C2—H2	126.6	C10—C11—C14	119.86 (17)
C3—C2—H2	126.6	C6—C11—C14	121.00 (16)
C4—C3—C2	108.33 (16)	C7—C12—H12A	109.5
C4—C3—H3	125.8	C7—C12—H12B	109.5
C2—C3—H3	125.8	H12A—C12—H12B	109.5
N1—C4—C3	107.28 (15)	C7—C12—H12C	109.5
N1—C4—C5	124.72 (16)	H12A—C12—H12C	109.5
C3—C4—C5	127.83 (17)	H12B—C12—H12C	109.5
N2—C5—C4	125.03 (17)	C9—C13—H13A	109.5
N2—C5—H5	117.5	C9—C13—H13B	109.5
C4—C5—H5	117.5	H13A—C13—H13B	109.5
C5—N2—C6	117.39 (15)	C9—C13—H13C	109.5
C7—C6—C11	120.09 (16)	H13A—C13—H13C	109.5
C7—C6—N2	121.12 (17)	H13B—C13—H13C	109.5
C11—C6—N2	118.70 (15)	C11—C14—H14A	109.5
C8—C7—C6	118.51 (18)	C11—C14—H14B	109.5
C8—C7—C12	120.33 (18)	H14A—C14—H14B	109.5
C6—C7—C12	121.15 (18)	C11—C14—H14C	109.5
C9—C8—C7	123.01 (18)	H14A—C14—H14C	109.5
C9—C8—H8	118.5	H14B—C14—H14C	109.5
C7—C8—H8	118.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.94 (2)	2.05 (2)	2.909 (2)	150.7 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.94 (2)	2.05 (2)	2.909 (2)	150.7 (17)

Symmetry code: (i) .