9-{4-[(E)-2-(4,6-Dimethyl-1,3,5-triazin-2-yl)ethen-yl]phen-yl}-9H-carbazole.

In the crystal structure of the title compound, C(25)H(20)N(4), the triazinyl ring is nearly coplanar with the planar (r.m.s. deviation = 0.028 Å) phenyl-ethenyl unit, the twist being only 5.8 (2)°; however, the planar carbazolyl unit (r.m.s. deviation = 0.008 Å) is twisted by 47.8 (1)° with respect to the phenyl-ethenyl unit. The nonplanar nature of the mol-ecule explains the phenomenon of light emission at short wavelengths in the solid state but at long wavelengths in solution.

Related literature

For background literature on donor–π-acceptor chromophores, see: Cui et al. (2003 ▶, 2004 ▶); Kannan et al. (2004 ▶); Maury & Bozec (2005 ▶); Zhong et al. (2008 ▶).

Experimental

Crystal data

C25H20N4

M = 376.45

Orthorhombic,

a = 8.0415 (8) Å

b = 15.716 (2) Å

c = 16.098 (1) Å

V = 2034.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.42 × 0.28 × 0.16 mm

Data collection

Siemens P4 four-circle diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.901, T max = 0.988

2991 measured reflections

2291 independent reflections

1288 reflections with I > 2σ(I)

R int = 0.026

3 standard reflections every 97 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.160

S = 1.00

2291 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.30 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030359/bt5017sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030359/bt5017Isup2.hkl

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

C25H20N4	F(000) = 792
Mr = 376.45	Dx = 1.229 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 40 reflections
a = 8.0415 (8) Å	θ = 4.6–12.4°
b = 15.716 (2) Å	µ = 0.07 mm−1
c = 16.098 (1) Å	T = 293 K
V = 2034.4 (3) Å3	Prism, pale green
Z = 4	0.42 × 0.28 × 0.16 mm

Siemens P4 four-circle diffractometer	1288 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 26.0°, θmin = 1.8°
ω scans	h = −1→9
Absorption correction: ψ scan (North et al., 1968)	k = −19→1
Tmin = 0.901, Tmax = 0.988	l = −19→1
2991 measured reflections	3 standard reflections every 97 reflections
2291 independent reflections	intensity decay: 1%

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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.160	w = 1/[σ2(Fo2) + (0.0785P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
2291 reflections	Δρmax = 0.26 e Å−3
265 parameters	Δρmin = −0.30 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: 0.063 (5)

	x	y	z	Uiso*/Ueq
N1	0.3440 (7)	0.5461 (3)	0.7650 (3)	0.0774 (15)
N2	0.2899 (6)	0.4809 (2)	0.6348 (2)	0.0627 (12)
N3	0.4255 (6)	0.4024 (3)	0.7419 (3)	0.0659 (12)
N4	0.3597 (5)	0.0613 (2)	0.3022 (2)	0.0511 (11)
C1	0.2848 (8)	0.5466 (3)	0.6880 (4)	0.0732 (17)
C2	0.4126 (8)	0.4724 (4)	0.7893 (3)	0.0727 (17)
C3	0.3621 (7)	0.4108 (3)	0.6658 (3)	0.0584 (14)
C4	0.2098 (9)	0.6278 (3)	0.6563 (4)	0.091 (2)
H4A	0.1203	0.6448	0.6921	0.137*
H4B	0.1680	0.6190	0.6011	0.137*
H4C	0.2932	0.6715	0.6554	0.137*
C5	0.4801 (8)	0.4663 (4)	0.8757 (3)	0.097 (2)
H5A	0.4946	0.4076	0.8903	0.146*
H5B	0.4036	0.4925	0.9137	0.146*
H5C	0.5853	0.4950	0.8785	0.146*
C6	0.3767 (7)	0.3359 (3)	0.6121 (3)	0.0563 (13)
H6	0.4272	0.2875	0.6337	0.068*
C7	0.3217 (7)	0.3333 (3)	0.5341 (3)	0.0539 (12)
H7	0.2704	0.3823	0.5144	0.065*
C8	0.3331 (7)	0.2616 (3)	0.4757 (3)	0.0498 (12)
C9	0.2847 (7)	0.2736 (3)	0.3941 (3)	0.0545 (13)
H9	0.2475	0.3269	0.3771	0.065*
C10	0.2910 (7)	0.2076 (3)	0.3373 (3)	0.0544 (13)
H10	0.2559	0.2166	0.2830	0.065*
C11	0.3490 (6)	0.1284 (3)	0.3607 (3)	0.0471 (12)
C12	0.3989 (7)	0.1159 (3)	0.4417 (3)	0.0537 (12)
H12	0.4389	0.0630	0.4581	0.064*
C13	0.3898 (7)	0.1816 (3)	0.4988 (3)	0.0563 (13)
H13	0.4223	0.1720	0.5534	0.068*
C14	0.4250 (6)	0.0677 (3)	0.2221 (3)	0.0503 (12)
C15	0.5018 (7)	0.1357 (3)	0.1836 (3)	0.0630 (14)
H15	0.5147	0.1875	0.2108	0.076*
C16	0.5584 (7)	0.1243 (4)	0.1036 (3)	0.0700 (15)
H16	0.6104	0.1693	0.0766	0.084*
C17	0.5401 (7)	0.0476 (4)	0.0625 (3)	0.0712 (16)
H17	0.5785	0.0419	0.0083	0.085*
C18	0.4658 (6)	−0.0198 (4)	0.1013 (3)	0.0636 (15)
H18	0.4539	−0.0713	0.0735	0.076*
C19	0.4080 (6)	−0.0115 (3)	0.1823 (3)	0.0521 (12)
C20	0.3274 (6)	−0.0680 (3)	0.2402 (3)	0.0520 (12)
C21	0.2764 (7)	−0.1526 (3)	0.2366 (3)	0.0662 (15)
H21	0.2946	−0.1844	0.1888	0.079*
C22	0.2003 (8)	−0.1884 (3)	0.3032 (3)	0.0733 (16)
H22	0.1661	−0.2448	0.3006	0.088*
C23	0.1725 (7)	−0.1418 (3)	0.3754 (3)	0.0688 (15)
H23	0.1202	−0.1675	0.4204	0.083*
C24	0.2220 (7)	−0.0573 (3)	0.3811 (3)	0.0624 (14)
H24	0.2028	−0.0260	0.4291	0.075*
C25	0.3004 (6)	−0.0213 (3)	0.3137 (3)	0.0520 (12)

	U11	U22	U33	U12	U13	U23
N1	0.088 (4)	0.069 (3)	0.075 (3)	−0.020 (3)	0.025 (3)	−0.033 (3)
N2	0.075 (3)	0.049 (2)	0.065 (2)	−0.009 (2)	0.021 (3)	−0.010 (2)
N3	0.077 (3)	0.064 (3)	0.056 (2)	−0.019 (3)	0.017 (3)	−0.019 (2)
N4	0.064 (3)	0.044 (2)	0.045 (2)	−0.002 (2)	0.001 (2)	−0.0078 (17)
C1	0.081 (4)	0.057 (3)	0.081 (4)	−0.021 (3)	0.031 (4)	−0.025 (3)
C2	0.075 (4)	0.083 (4)	0.060 (3)	−0.030 (4)	0.023 (3)	−0.023 (3)
C3	0.067 (4)	0.055 (3)	0.053 (3)	−0.015 (3)	0.017 (3)	−0.013 (2)
C4	0.108 (5)	0.053 (3)	0.114 (5)	0.003 (3)	0.038 (5)	−0.016 (3)
C5	0.099 (5)	0.126 (5)	0.066 (4)	−0.037 (4)	0.013 (4)	−0.041 (4)
C6	0.072 (4)	0.047 (3)	0.050 (3)	−0.008 (3)	0.011 (3)	−0.009 (2)
C7	0.065 (3)	0.043 (2)	0.053 (3)	−0.005 (3)	0.008 (3)	−0.004 (2)
C8	0.060 (3)	0.041 (2)	0.049 (3)	−0.005 (2)	0.004 (3)	−0.007 (2)
C9	0.071 (4)	0.040 (2)	0.052 (3)	0.006 (3)	0.001 (3)	−0.005 (2)
C10	0.071 (3)	0.047 (3)	0.046 (2)	0.004 (3)	−0.002 (3)	−0.005 (2)
C11	0.056 (3)	0.043 (2)	0.043 (2)	0.000 (2)	0.001 (2)	−0.008 (2)
C12	0.071 (3)	0.042 (2)	0.048 (3)	0.004 (3)	−0.006 (3)	−0.006 (2)
C13	0.074 (4)	0.051 (3)	0.043 (2)	−0.001 (3)	−0.004 (3)	−0.007 (2)
C14	0.052 (3)	0.054 (3)	0.044 (3)	0.006 (3)	0.000 (2)	−0.006 (2)
C15	0.074 (4)	0.063 (3)	0.051 (3)	−0.003 (3)	0.002 (3)	−0.006 (3)
C16	0.077 (4)	0.084 (4)	0.049 (3)	−0.005 (4)	0.007 (3)	−0.001 (3)
C17	0.074 (4)	0.094 (4)	0.045 (3)	0.007 (4)	0.003 (3)	−0.006 (3)
C18	0.064 (4)	0.076 (3)	0.050 (3)	0.011 (3)	−0.006 (3)	−0.026 (3)
C19	0.051 (3)	0.057 (3)	0.048 (3)	0.008 (3)	−0.007 (2)	−0.010 (2)
C20	0.053 (3)	0.047 (3)	0.056 (3)	0.006 (2)	−0.009 (3)	−0.012 (2)
C21	0.072 (4)	0.054 (3)	0.072 (3)	0.004 (3)	−0.011 (3)	−0.019 (3)
C22	0.091 (4)	0.047 (3)	0.082 (4)	−0.001 (3)	−0.005 (4)	−0.007 (3)
C23	0.078 (4)	0.057 (3)	0.072 (3)	−0.004 (3)	0.008 (3)	0.003 (3)
C24	0.073 (4)	0.049 (3)	0.065 (3)	0.003 (3)	0.007 (3)	−0.008 (2)
C25	0.057 (3)	0.044 (2)	0.055 (3)	0.004 (2)	−0.005 (3)	−0.004 (2)

N1—C1	1.328 (7)	C10—H10	0.9300
N1—C2	1.342 (7)	C11—C12	1.378 (6)
N2—C1	1.341 (5)	C12—C13	1.384 (6)
N2—C3	1.341 (6)	C12—H12	0.9300
N3—C3	1.333 (6)	C13—H13	0.9300
N3—C2	1.342 (6)	C14—C15	1.382 (6)
N4—C25	1.396 (6)	C14—C19	1.406 (6)
N4—C14	1.396 (5)	C15—C16	1.378 (6)
N4—C11	1.416 (5)	C15—H15	0.9300
C1—C4	1.500 (7)	C16—C17	1.382 (7)
C2—C5	1.496 (8)	C16—H16	0.9300
C3—C6	1.465 (6)	C17—C18	1.367 (7)
C4—H4A	0.9600	C17—H17	0.9300
C4—H4B	0.9600	C18—C19	1.391 (6)
C4—H4C	0.9600	C18—H18	0.9300
C5—H5A	0.9600	C19—C20	1.441 (6)
C5—H5B	0.9600	C20—C21	1.393 (6)
C5—H5C	0.9600	C20—C25	1.408 (6)
C6—C7	1.332 (6)	C21—C22	1.357 (7)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.471 (5)	C22—C23	1.392 (7)
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.383 (6)	C23—C24	1.389 (6)
C8—C13	1.388 (6)	C23—H23	0.9300
C9—C10	1.383 (6)	C24—C25	1.377 (6)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.382 (6)
C1—N1—C2	115.1 (4)	C10—C11—N4	120.6 (4)
C1—N2—C3	114.1 (4)	C11—C12—C13	120.4 (4)
C3—N3—C2	114.3 (5)	C11—C12—H12	119.8
C25—N4—C14	108.5 (4)	C13—C12—H12	119.8
C25—N4—C11	125.8 (4)	C12—C13—C8	121.0 (4)
C14—N4—C11	125.7 (4)	C12—C13—H13	119.5
N1—C1—N2	125.4 (5)	C8—C13—H13	119.5
N1—C1—C4	117.8 (5)	C15—C14—N4	129.6 (4)
N2—C1—C4	116.7 (5)	C15—C14—C19	121.6 (4)
N3—C2—N1	125.0 (5)	N4—C14—C19	108.8 (4)
N3—C2—C5	116.6 (6)	C16—C15—C14	117.8 (5)
N1—C2—C5	118.3 (5)	C16—C15—H15	121.1
N3—C3—N2	126.1 (4)	C14—C15—H15	121.1
N3—C3—C6	115.6 (5)	C15—C16—C17	121.8 (5)
N2—C3—C6	118.4 (4)	C15—C16—H16	119.1
C1—C4—H4A	109.5	C17—C16—H16	119.1
C1—C4—H4B	109.5	C18—C17—C16	120.2 (5)
H4A—C4—H4B	109.5	C18—C17—H17	119.9
C1—C4—H4C	109.5	C16—C17—H17	119.9
H4A—C4—H4C	109.5	C17—C18—C19	120.1 (5)
H4B—C4—H4C	109.5	C17—C18—H18	120.0
C2—C5—H5A	109.5	C19—C18—H18	120.0
C2—C5—H5B	109.5	C18—C19—C14	118.6 (5)
H5A—C5—H5B	109.5	C18—C19—C20	134.3 (5)
C2—C5—H5C	109.5	C14—C19—C20	107.1 (4)
H5A—C5—H5C	109.5	C21—C20—C25	119.1 (5)
H5B—C5—H5C	109.5	C21—C20—C19	133.9 (5)
C7—C6—C3	123.6 (5)	C25—C20—C19	107.0 (4)
C7—C6—H6	118.2	C22—C21—C20	119.7 (5)
C3—C6—H6	118.2	C22—C21—H21	120.1
C6—C7—C8	127.3 (5)	C20—C21—H21	120.1
C6—C7—H7	116.4	C21—C22—C23	121.0 (5)
C8—C7—H7	116.4	C21—C22—H22	119.5
C9—C8—C13	118.1 (4)	C23—C22—H22	119.5
C9—C8—C7	119.0 (4)	C24—C23—C22	120.8 (5)
C13—C8—C7	122.9 (4)	C24—C23—H23	119.6
C8—C9—C10	121.0 (4)	C22—C23—H23	119.6
C8—C9—H9	119.5	C25—C24—C23	118.2 (5)
C10—C9—H9	119.5	C25—C24—H24	120.9
C9—C10—C11	120.5 (4)	C23—C24—H24	120.9
C9—C10—H10	119.8	C24—C25—N4	130.0 (4)
C11—C10—H10	119.8	C24—C25—C20	121.2 (4)
C12—C11—C10	119.0 (4)	N4—C25—C20	108.7 (4)
C12—C11—N4	120.3 (4)
C2—N1—C1—N2	−0.5 (9)	C25—N4—C14—C19	−0.3 (5)
C2—N1—C1—C4	−178.7 (5)	C11—N4—C14—C19	−177.8 (4)
C3—N2—C1—N1	0.1 (8)	N4—C14—C15—C16	178.7 (5)
C3—N2—C1—C4	178.3 (5)	C19—C14—C15—C16	1.4 (8)
C3—N3—C2—N1	−0.4 (8)	C14—C15—C16—C17	0.0 (8)
C3—N3—C2—C5	179.4 (5)	C15—C16—C17—C18	−0.7 (9)
C1—N1—C2—N3	0.7 (9)	C16—C17—C18—C19	0.1 (8)
C1—N1—C2—C5	−179.2 (5)	C17—C18—C19—C14	1.2 (7)
C2—N3—C3—N2	0.0 (8)	C17—C18—C19—C20	−179.4 (5)
C2—N3—C3—C6	179.0 (4)	C15—C14—C19—C18	−1.9 (7)
C1—N2—C3—N3	0.1 (8)	N4—C14—C19—C18	−179.8 (4)
C1—N2—C3—C6	−178.9 (5)	C15—C14—C19—C20	178.5 (5)
N3—C3—C6—C7	−179.4 (5)	N4—C14—C19—C20	0.6 (5)
N2—C3—C6—C7	−0.3 (8)	C18—C19—C20—C21	−0.2 (10)
C3—C6—C7—C8	179.2 (5)	C14—C19—C20—C21	179.3 (5)
C6—C7—C8—C9	−173.2 (5)	C18—C19—C20—C25	179.7 (5)
C6—C7—C8—C13	7.1 (8)	C14—C19—C20—C25	−0.8 (5)
C13—C8—C9—C10	0.7 (8)	C25—C20—C21—C22	0.7 (8)
C7—C8—C9—C10	−179.1 (5)	C19—C20—C21—C22	−179.3 (6)
C8—C9—C10—C11	−1.3 (8)	C20—C21—C22—C23	−0.2 (9)
C9—C10—C11—C12	0.7 (8)	C21—C22—C23—C24	0.1 (9)
C9—C10—C11—N4	−178.3 (5)	C22—C23—C24—C25	−0.5 (8)
C25—N4—C11—C12	49.7 (7)	C23—C24—C25—N4	178.9 (5)
C14—N4—C11—C12	−133.2 (5)	C23—C24—C25—C20	1.1 (8)
C25—N4—C11—C10	−131.3 (5)	C14—N4—C25—C24	−178.2 (5)
C14—N4—C11—C10	45.8 (7)	C11—N4—C25—C24	−0.7 (8)
C10—C11—C12—C13	0.5 (8)	C14—N4—C25—C20	−0.2 (5)
N4—C11—C12—C13	179.5 (5)	C11—N4—C25—C20	177.3 (4)
C11—C12—C13—C8	−1.0 (8)	C21—C20—C25—C24	−1.2 (7)
C9—C8—C13—C12	0.4 (8)	C19—C20—C25—C24	178.8 (4)
C7—C8—C13—C12	−179.8 (5)	C21—C20—C25—N4	−179.4 (5)
C25—N4—C14—C15	−177.9 (5)	C19—C20—C25—N4	0.6 (5)
C11—N4—C14—C15	4.6 (8)