N-[(E)-(9-Ethyl-9H-carbazol-3-yl)methyl­idene]aniline

Yeksan, N.; Uzkara, E.; Zeybek, O.; Asker, E.

doi:10.1107/S1600536810018660

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1456

https://doi.org/10.1107/S1600536810018660

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N-[(E)-(9-Ethyl-9H-carbazol-3-yl)methylidene]aniline

Nuray Yeksan,^a Ece Uzkara,^a Orhan Zeybek ^a and Erol Asker ^b ^*

^aDepartment of Physics, Faculty of Arts and Sciences, Balıkesir University, 10615 Cağış–Balıkesir, Turkey, and ^bNecatibey Faculty of Education, Balıkesir University, 10100 Balıkesir, Turkey
^*Correspondence e-mail: asker@balikesir.edu.tr

(Received 3 May 2010; accepted 19 May 2010; online 26 May 2010)

The title compound, C₂₁H₁₈N₂, 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 interactions between the carbazole benzene rings and the methylene 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_r = 298.37
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.062
wR(F²) = 0.148
S = 1.41
2838 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.13 e Å⁻³

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) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z.

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810018660/om2337Isup2.hkl

checkCIF report

Comment top

The structure of the title compound is depicted in (Fig. 1). The bond lengths and internal bond angles of the carbazole skeleton are comparable to those of related molecules (Wang et al., 2008; Huang et al., 2008). The carbazole and phenyl skeletons are essentially planar with r.m.s deviations of 0.021Å (carbazole ring) and 0.008Å (phenyl ring). The phenyl ring is twisted away from the carbazole ring by 67.45 (05)°. The ethyl group protrudes out of the plane of the carbazole skeleton as indicated by the C9A—N9—C10—C11 torsion angle of 86.0 (3)°. The only force that stack the molecules appears to be π-ring C—H···Cg intermolecular interactions among the benzene rings of carbazole and the hydrogen atoms H5, H10A and H12 (Fig. 2).

Related literature top

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 top

The title compound was synthesized via the imine reaction between aniline and 9-ethyl-9H-carbazol-3-carbaldehyde in ethanol. In a round bottom flask fitted with a magnetic stirrer a solution was prepared from 9-ethyl-9H-carbazol-3-carbaldehyde (1.116 g, 5 mmol) and aniline (0.70 g, 7.5 mmol) in 50 ml ethanol at ambient temperature. After stirring for 2 h, the solution was left for crystallization overnight, after which time the product was precipitated as yellow crystals. The crude product was separated by filtration and washed with ethanol. Yellow, transparent crystals suitable for the X-ray diffraction analysis were grown from tetrahydrofuran by slow evaporation technique at ambient temperature, mp. 407 K. FT—IR (KBr) ν_max (cm^-1): 3048 (Ar—H), 2973 (-CH₃), 2930 (-CH₂-), 1618 (C=N), 1587, 1567 (Ar—N), 1489, 1473, 1461 (Ar C=C); ¹HNMR (300 MHz, CDCl₃, ppm): 1.46 (t, J = 7.3 Hz, 3H, CH₃), 4.38 (q, J = 7.3 Hz, 2H, -CH₂-), 7.21-7.59 (m, 9H, ArH), 8.07 (dd, J = 8.5 and 1.8 Hz, 1H, H2), 8.18 (dt, J = 7.9 and 0.8 Hz, 1H, H5), 8.64 (s, 1H, H12), 8.65 (d, J= 1.8, 1H, H4). UV-Vis, [EtOH, λmax (nm), (ε)] = 238 (25800), 293 (22100), 338 (18500).

Structure description top

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).

Computing details top

Data collection: CrystalStructure (Rigaku & Rigaku/MSC, 2003); cell refinement: CrystalStructure (Rigaku & Rigaku/MSC, 2003); 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).

Figures top

	Fig. 1. The structure of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level and arbitrary spheres are shown for the H atoms.
	Fig. 2. Packing diagram of showing C—H···Cg intermolecular interactions; red spheres represent ring centroids.

N-[(E)-(9-Ethyl-9H-carbazol-3-yl)methylidene]aniline top

Crystal data top

C₂₁H₁₈N₂	F(000) = 632
M_r = 298.37	D_x = 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

Data collection top

Rigaku R-AXIS RAPID S diffractometer	R_int = 0.030
Graphite monochromator	θ_max = 25.2°, θ_min = 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 top

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(F_o²) + (0.0417P)² + 0.4831P] where P = (F_o² + 2F_c²)/3
S = 1.41	(Δ/σ)_max = 0.002
2838 reflections	Δρ_max = 0.14 e Å⁻³
209 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0123 (17)

Crystal data top

C₂₁H₁₈N₂	V = 1605.7 (3) Å³
M_r = 298.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.3350 (3) Å	µ = 0.07 mm⁻¹
b = 5.9692 (10) Å	T = 295 K
c = 17.5447 (3) Å	0.6 × 0.4 × 0.2 mm
β = 91.162 (1)°

Data collection top

Rigaku R-AXIS RAPID S diffractometer	2821 reflections with I > 2σ(I)
28963 measured reflections	R_int = 0.030
2838 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.41	Δρ_max = 0.14 e Å⁻³
2838 reflections	Δρ_min = −0.13 e Å⁻³
209 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+1/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈N₂
M_r	298.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	15.3350 (3), 5.9692 (10), 17.5447 (3)
β (°)	91.162 (1)
V (Å³)	1605.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.6 × 0.4 × 0.2

Data collection
Diffractometer	Rigaku R-AXIS RAPID S
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	28963, 2838, 2821
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.148, 1.41
No. of reflections	2838
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.13

Computer programs: CrystalStructure (Rigaku & Rigaku/MSC, 2003), SORTAV (Blessing, 1995), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected torsion angles (º) top

C9A—N9—C10—C11	−86.0 (3)	C2—C3—C12—N1	−10.7 (3)
C13—N1—C12—C3	178.29 (19)	C12—N1—C13—C14	−56.6 (3)

Hydrogen-bond geometry (Å, º) top

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)	134.7
C12—H12···Cg2ⁱ	0.93	2.98	3.660 (3)	130.9
C10—H10A···Cg2ⁱⁱ	0.97	3.25	4.050 (4)	141.6

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, y+1, z.

Acknowledgements

The authors thank the Scientific Research Projects Department (BAP) at Balikesir University for financial support (Project No. 08/06).

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Grigoras, M. & Antonoaia, N. C. (2005). Eur. Polym. J. 41, 1079–1089. Web of Science CrossRef CAS Google Scholar
Huang, P.-H., Chen, G.-J. & Wen, Y.-S. (2008). Acta Cryst. E64, o2407. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku & Rigaku/MSC (2003). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Segura, J. L. (1998). Acta Polym. 49, 319–344. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, J. J., Zhang, X., Zhang, B. Q., Wang, G. & Yu, X. Q. (2008). Acta Cryst. E64, o1293. Web of Science CSD CrossRef IUCr Journals Google Scholar

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