N-[(E)-(9-Ethyl-9H-carbazol-3-yl)methyl-idene]aniline.

The title compound, C(21)H(18)N(2), was obtained as the product of the reaction between 9-ethyl-9H-carbazole-3-carbaldehyde and aniline in ethanol. The crystal packing is stabilized mainly by C-H⋯π inter-actions between the carbazole benzene rings and the methyl-ene H atoms.

Related literature

For background to photoconductive properties see: Segura (1998 ▶); Grigoras & Antonoaia (2005 ▶). For geometrical parameters in related structures, see: Wang et al. (2008 ▶); Huang et al. (2008 ▶).

Experimental

Crystal data

C21H18N2

M = 298.37

Monoclinic,

a = 15.3350 (3) Å

b = 5.9692 (10) Å

c = 17.5447 (3) Å

β = 91.162 (1)°

V = 1605.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.6 × 0.4 × 0.2 mm

Data collection

Rigaku R-AXIS RAPID S diffractometer

28963 measured reflections

2838 independent reflections

2821 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.148

S = 1.41

2838 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrystalStructure (Rigaku & Rigaku/MSC, 2003 ▶); cell refinement: CrystalStructure; data reduction: SORTAV (Blessing, 1995 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018660/om2337sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018660/om2337Isup2.hkl

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

C21H18N2	F(000) = 632
Mr = 298.37	Dx = 1.234 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8828 reflections
a = 15.3350 (3) Å	θ = 2.3–25.3°
b = 5.9692 (10) Å	µ = 0.07 mm−1
c = 17.5447 (3) Å	T = 295 K
β = 91.162 (1)°	Prism, yellow
V = 1605.7 (3) Å3	0.6 × 0.4 × 0.2 mm
Z = 4

Rigaku R-AXIS RAPID S diffractometer	Rint = 0.030
graphite	θmax = 25.2°, θmin = 2.3°
ω scans	h = −18→18
28963 measured reflections	k = −6→7
2838 independent reflections	l = −20→20
2821 reflections with I > 2σ(I)

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)] = 0.062	H-atom parameters constrained
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0417P)2 + 0.4831P] where P = (Fo2 + 2Fc2)/3
S = 1.41	(Δ/σ)max = 0.002
2838 reflections	Δρmax = 0.14 e Å−3
209 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0123 (17)

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 > 2σ(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	0.53644 (12)	−0.2326 (3)	0.39241 (11)	0.0627 (5)
N9	0.15252 (12)	0.1918 (3)	0.39179 (10)	0.0567 (5)
C1	0.31091 (15)	0.1662 (4)	0.42835 (13)	0.0583 (6)
H1	0.3127	0.2991	0.456	0.07*
C2	0.38396 (14)	0.0359 (4)	0.42111 (12)	0.0580 (6)
H2	0.436	0.0829	0.444	0.07*
C3	0.38256 (14)	−0.1669 (4)	0.38000 (12)	0.0530 (5)
C4	0.30554 (14)	−0.2380 (4)	0.34500 (12)	0.0531 (5)
H4	0.304	−0.3717	0.3178	0.064*
C4A	0.23047 (13)	−0.1080 (4)	0.35070 (11)	0.0511 (5)
C4B	0.14167 (13)	−0.1318 (4)	0.32328 (11)	0.0520 (5)
C5	0.09773 (15)	−0.2925 (4)	0.27965 (12)	0.0611 (6)
H5	0.1274	−0.4154	0.2605	0.073*
C6	0.00979 (16)	−0.2669 (5)	0.26525 (14)	0.0678 (7)
H6	−0.0202	−0.3737	0.2364	0.081*
C7	−0.03468 (16)	−0.0827 (5)	0.29346 (14)	0.0684 (7)
H7	−0.0942	−0.0697	0.2833	0.082*
C8	0.00672 (15)	0.0809 (4)	0.33593 (13)	0.0636 (6)
H8	−0.0235	0.2044	0.354	0.076*
C8A	0.09549 (14)	0.0541 (4)	0.35072 (11)	0.0542 (5)
C9A	0.23398 (14)	0.0931 (4)	0.39289 (11)	0.0522 (5)
C10	0.12624 (16)	0.3717 (4)	0.44220 (14)	0.0651 (6)
H10A	0.0808	0.4594	0.4171	0.078*
H10B	0.1757	0.4697	0.452	0.078*
C11	0.0931 (2)	0.2849 (5)	0.51707 (15)	0.0874 (9)
H11A	0.0766	0.4088	0.5486	0.131*
H11B	0.1382	0.2003	0.5425	0.131*
H11C	0.0434	0.1904	0.5077	0.131*
C12	0.46110 (14)	−0.3017 (4)	0.37283 (12)	0.0553 (5)
H12	0.4557	−0.4456	0.3529	0.066*
C13	0.60811 (14)	−0.3801 (4)	0.38491 (12)	0.0550 (5)
C14	0.61128 (15)	−0.5881 (4)	0.41922 (13)	0.0636 (6)
H14	0.5646	−0.6363	0.448	0.076*
C15	0.68271 (18)	−0.7249 (5)	0.41133 (16)	0.0767 (7)
H15	0.6844	−0.8639	0.4352	0.092*
C16	0.75146 (18)	−0.6566 (5)	0.36830 (18)	0.0818 (8)
H16	0.7992	−0.7505	0.362	0.098*
C17	0.74958 (16)	−0.4498 (5)	0.33467 (16)	0.0795 (8)
H17	0.7964	−0.4032	0.3057	0.095*
C18	0.67877 (15)	−0.3096 (4)	0.34333 (14)	0.0674 (6)
H18	0.6786	−0.1679	0.3212	0.081*

	U11	U22	U33	U12	U13	U23
N1	0.0557 (11)	0.0652 (12)	0.0671 (12)	0.0002 (9)	−0.0018 (9)	−0.0068 (10)
N9	0.0579 (11)	0.0550 (11)	0.0573 (10)	0.0052 (9)	0.0051 (8)	−0.0043 (9)
C1	0.0646 (13)	0.0538 (13)	0.0566 (12)	−0.0033 (11)	0.0010 (10)	−0.0071 (10)
C2	0.0570 (12)	0.0616 (14)	0.0553 (12)	−0.0056 (11)	−0.0028 (10)	−0.0016 (11)
C3	0.0549 (12)	0.0564 (13)	0.0477 (11)	0.0000 (10)	0.0020 (9)	0.0005 (10)
C4	0.0592 (12)	0.0516 (12)	0.0485 (11)	−0.0004 (10)	0.0014 (9)	−0.0044 (9)
C4A	0.0549 (12)	0.0514 (12)	0.0470 (11)	−0.0026 (10)	0.0012 (9)	0.0000 (9)
C4B	0.0558 (12)	0.0567 (12)	0.0435 (10)	−0.0015 (10)	0.0022 (9)	0.0047 (9)
C5	0.0686 (14)	0.0626 (14)	0.0519 (12)	−0.0042 (11)	−0.0041 (10)	−0.0013 (11)
C6	0.0647 (14)	0.0795 (17)	0.0589 (13)	−0.0129 (13)	−0.0095 (11)	0.0054 (12)
C7	0.0551 (13)	0.0889 (19)	0.0611 (14)	−0.0045 (13)	−0.0032 (11)	0.0162 (13)
C8	0.0590 (13)	0.0738 (16)	0.0582 (13)	0.0065 (12)	0.0053 (10)	0.0093 (12)
C8A	0.0573 (12)	0.0593 (13)	0.0461 (11)	−0.0012 (10)	0.0037 (9)	0.0062 (10)
C9A	0.0569 (12)	0.0518 (12)	0.0480 (11)	0.0003 (10)	0.0051 (9)	0.0009 (9)
C10	0.0702 (15)	0.0567 (13)	0.0688 (15)	0.0077 (12)	0.0092 (12)	−0.0066 (11)
C11	0.101 (2)	0.102 (2)	0.0603 (15)	0.0029 (18)	0.0132 (14)	−0.0073 (15)
C12	0.0577 (13)	0.0579 (13)	0.0505 (12)	−0.0021 (10)	0.0031 (9)	−0.0029 (10)
C13	0.0519 (12)	0.0608 (13)	0.0524 (12)	−0.0049 (10)	−0.0024 (9)	−0.0068 (10)
C14	0.0626 (14)	0.0665 (15)	0.0619 (14)	−0.0044 (12)	0.0076 (11)	−0.0003 (11)
C15	0.0802 (17)	0.0668 (16)	0.0833 (18)	0.0074 (14)	0.0044 (14)	0.0030 (14)
C16	0.0649 (16)	0.082 (2)	0.099 (2)	0.0120 (14)	0.0043 (14)	−0.0125 (17)
C17	0.0560 (14)	0.093 (2)	0.0902 (19)	−0.0115 (14)	0.0155 (13)	−0.0126 (16)
C18	0.0640 (14)	0.0665 (15)	0.0720 (15)	−0.0111 (12)	0.0052 (12)	−0.0017 (12)

N1—C12	1.268 (3)	C7—C8	1.376 (3)
N1—C13	1.416 (3)	C7—H7	0.93
N9—C9A	1.381 (3)	C8—C8A	1.390 (3)
N9—C8A	1.391 (3)	C8—H8	0.93
N9—C10	1.453 (3)	C10—C11	1.510 (3)
C1—C2	1.372 (3)	C10—H10A	0.97
C1—C9A	1.393 (3)	C10—H10B	0.97
C1—H1	0.93	C11—H11A	0.96
C2—C3	1.409 (3)	C11—H11B	0.96
C2—H2	0.93	C11—H11C	0.96
C3—C4	1.386 (3)	C12—H12	0.93
C3—C12	1.456 (3)	C13—C14	1.380 (3)
C4—C4A	1.393 (3)	C13—C18	1.384 (3)
C4—H4	0.93	C14—C15	1.375 (3)
C4A—C9A	1.411 (3)	C14—H14	0.93
C4A—C4B	1.442 (3)	C15—C16	1.371 (4)
C4B—C5	1.393 (3)	C15—H15	0.93
C4B—C8A	1.407 (3)	C16—C17	1.368 (4)
C5—C6	1.376 (3)	C16—H16	0.93
C5—H5	0.93	C17—C18	1.382 (4)
C6—C7	1.390 (4)	C17—H17	0.93
C6—H6	0.93	C18—H18	0.93
C12—N1—C13	118.5 (2)	N9—C9A—C1	129.1 (2)
C9A—N9—C8A	108.32 (18)	N9—C9A—C4A	109.32 (18)
C9A—N9—C10	124.65 (19)	C1—C9A—C4A	121.6 (2)
C8A—N9—C10	124.95 (19)	N9—C10—C11	112.2 (2)
C2—C1—C9A	117.8 (2)	N9—C10—H10A	109.2
C2—C1—H1	121.1	C11—C10—H10A	109.2
C9A—C1—H1	121.1	N9—C10—H10B	109.2
C1—C2—C3	122.0 (2)	C11—C10—H10B	109.2
C1—C2—H2	119	H10A—C10—H10B	107.9
C3—C2—H2	119	C10—C11—H11A	109.5
C4—C3—C2	119.6 (2)	C10—C11—H11B	109.5
C4—C3—C12	119.4 (2)	H11A—C11—H11B	109.5
C2—C3—C12	121.0 (2)	C10—C11—H11C	109.5
C3—C4—C4A	119.7 (2)	H11A—C11—H11C	109.5
C3—C4—H4	120.1	H11B—C11—H11C	109.5
C4A—C4—H4	120.1	N1—C12—C3	123.2 (2)
C4—C4A—C9A	119.24 (19)	N1—C12—H12	118.4
C4—C4A—C4B	134.2 (2)	C3—C12—H12	118.4
C9A—C4A—C4B	106.53 (18)	C14—C13—C18	118.8 (2)
C5—C4B—C8A	119.4 (2)	C14—C13—N1	122.6 (2)
C5—C4B—C4A	134.0 (2)	C18—C13—N1	118.5 (2)
C8A—C4B—C4A	106.66 (19)	C15—C14—C13	120.7 (2)
C6—C5—C4B	119.1 (2)	C15—C14—H14	119.6
C6—C5—H5	120.5	C13—C14—H14	119.6
C4B—C5—H5	120.5	C16—C15—C14	120.1 (3)
C5—C6—C7	120.6 (2)	C16—C15—H15	119.9
C5—C6—H6	119.7	C14—C15—H15	119.9
C7—C6—H6	119.7	C17—C16—C15	119.7 (3)
C8—C7—C6	122.0 (2)	C17—C16—H16	120.1
C8—C7—H7	119	C15—C16—H16	120.1
C6—C7—H7	119	C16—C17—C18	120.6 (2)
C7—C8—C8A	117.3 (2)	C16—C17—H17	119.7
C7—C8—H8	121.3	C18—C17—H17	119.7
C8A—C8—H8	121.3	C17—C18—C13	119.9 (2)
N9—C8A—C8	129.2 (2)	C17—C18—H18	120
N9—C8A—C4B	109.14 (18)	C13—C18—H18	120
C8—C8A—C4B	121.7 (2)
C9A—C1—C2—C3	−0.6 (3)	C8A—N9—C9A—C1	−178.4 (2)
C1—C2—C3—C4	0.5 (3)	C10—N9—C9A—C1	−14.2 (4)
C1—C2—C3—C12	179.7 (2)	C8A—N9—C9A—C4A	1.4 (2)
C2—C3—C4—C4A	0.1 (3)	C10—N9—C9A—C4A	165.58 (19)
C12—C3—C4—C4A	−179.05 (19)	C2—C1—C9A—N9	179.7 (2)
C3—C4—C4A—C9A	−0.7 (3)	C2—C1—C9A—C4A	0.0 (3)
C3—C4—C4A—C4B	−178.9 (2)	C4—C4A—C9A—N9	−179.11 (19)
C4—C4A—C4B—C5	−1.2 (4)	C4B—C4A—C9A—N9	−0.5 (2)
C9A—C4A—C4B—C5	−179.6 (2)	C4—C4A—C9A—C1	0.7 (3)
C4—C4A—C4B—C8A	177.8 (2)	C4B—C4A—C9A—C1	179.34 (19)
C9A—C4A—C4B—C8A	−0.6 (2)	C9A—N9—C10—C11	−86.0 (3)
C8A—C4B—C5—C6	−0.8 (3)	C8A—N9—C10—C11	75.7 (3)
C4A—C4B—C5—C6	178.0 (2)	C13—N1—C12—C3	178.29 (19)
C4B—C5—C6—C7	0.3 (3)	C4—C3—C12—N1	168.4 (2)
C5—C6—C7—C8	0.5 (4)	C2—C3—C12—N1	−10.7 (3)
C6—C7—C8—C8A	−0.8 (3)	C12—N1—C13—C14	−56.6 (3)
C9A—N9—C8A—C8	178.3 (2)	C12—N1—C13—C18	125.4 (2)
C10—N9—C8A—C8	14.1 (4)	C18—C13—C14—C15	−1.0 (3)
C9A—N9—C8A—C4B	−1.7 (2)	N1—C13—C14—C15	−179.1 (2)
C10—N9—C8A—C4B	−165.92 (19)	C13—C14—C15—C16	−0.8 (4)
C7—C8—C8A—N9	−179.8 (2)	C14—C15—C16—C17	1.5 (4)
C7—C8—C8A—C4B	0.3 (3)	C15—C16—C17—C18	−0.4 (4)
C5—C4B—C8A—N9	−179.41 (18)	C16—C17—C18—C13	−1.5 (4)
C4A—C4B—C8A—N9	1.4 (2)	C14—C13—C18—C17	2.1 (3)
C5—C4B—C8A—C8	0.5 (3)	N1—C13—C18—C17	−179.7 (2)
C4A—C4B—C8A—C8	−178.60 (19)

Cg1 and Cg2 are the centroids of the C1–C4/C4A/C9A and C4B/C5–C8/C8A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1i	0.93	2.87	3.587 (3)	135
C12—H12···Cg2i	0.93	2.98	3.660 (3)	131
C10—H10A···Cg2ii	0.97	3.25	4.050 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C4/C4A/C9A and C4B/C5–C8/C8A rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1i	0.93	2.87	3.587 (3)	135
C12—H12⋯Cg2i	0.93	2.98	3.660 (3)	131
C10—H10A⋯Cg2ii	0.97	3.25	4.050 (4)	142

Symmetry codes: (i) ; (ii) .