(E)-2-{3-[4-(Diphenyl-amino)styr-yl]-5,5-dimethyl-cyclo-hex-2-enyl-idene}-malono-nitrile.

In the title compound, C(31)H(27)N(3), the cyclo-hexene ring has an envelope configuration. In the crystal structure, there is an 34 Å(3) void around the inversion center, but the low electron density (0.13 e Å(-3)) in the difference Fourier map suggests no solvent mol-ecule occupying this void. No hydrogen bonding is found in the crystal structure.

Related literature

For background to organic compounds with light emitting properties, see: Tang et al. (1998 ▶); Li et al. (2003 ▶); Hye et al. (2004 ▶). For the synthesis, see: Lemke (1974 ▶); Tao & Miyata (2001 ▶). For related crystal structures, see: Kia et al. (2009 ▶); Ju et al. (2006 ▶).

Experimental

Crystal data

C31H27N3

M = 441.56

Monoclinic,

a = 13.239 (5) Å

b = 16.757 (8) Å

c = 11.886 (3) Å

β = 104.073 (5)°

V = 2557.7 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.48 × 0.19 × 0.16 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: none

20681 measured reflections

5879 independent reflections

3554 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.167

S = 0.92

5879 reflections

309 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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/S1600536809014378/xu2505sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014378/xu2505Isup2.hkl

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

C31H27N3	F(000) = 936
Mr = 441.56	Dx = 1.147 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 962 reflections
a = 13.239 (5) Å	θ = 2.4–20.0°
b = 16.757 (8) Å	µ = 0.07 mm−1
c = 11.886 (3) Å	T = 293 K
β = 104.073 (5)°	Block, red
V = 2557.7 (17) Å3	0.48 × 0.19 × 0.16 mm
Z = 4

Bruker SMART area-detector diffractometer	3554 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
graphite	θmax = 27.5°, θmin = 1.6°
φ and ω scans	h = −17→17
20681 measured reflections	k = −21→20
5879 independent reflections	l = −15→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.1P)2 + 0.187P] where P = (Fo2 + 2Fc2)/3
5879 reflections	(Δ/σ)max < 0.001
309 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.18 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 > 2sigma (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	0.81570 (11)	0.18274 (8)	0.93407 (11)	0.0627 (4)
N2	0.43530 (17)	0.55197 (11)	0.20566 (18)	0.1061 (6)
N3	0.21605 (14)	0.45416 (10)	−0.09927 (15)	0.0845 (5)
C1	0.7581 (2)	0.01018 (13)	1.1028 (2)	0.0974 (7)
H1	0.7009	−0.0186	1.1131	0.117*
C2	0.8549 (3)	−0.01085 (14)	1.1632 (2)	0.1187 (10)
H2	0.8641	−0.0534	1.2148	0.142*
C3	0.9377 (2)	0.03051 (15)	1.1477 (2)	0.1226 (10)
H3	1.0043	0.0163	1.1891	0.147*
C4	0.92488 (17)	0.09351 (13)	1.07133 (19)	0.0943 (7)
H4	0.9830	0.1213	1.0615	0.113*
C5	0.82738 (14)	0.11594 (10)	1.00942 (13)	0.0585 (4)
C6	0.74278 (16)	0.07411 (11)	1.02576 (16)	0.0741 (5)
H6	0.6758	0.0884	0.9856	0.089*
C7	0.86935 (13)	0.28927 (10)	1.07559 (14)	0.0600 (4)
H7	0.8285	0.2669	1.1209	0.072*
C8	0.92347 (14)	0.35847 (11)	1.11063 (15)	0.0692 (5)
H8	0.9191	0.3828	1.1796	0.083*
C9	0.98393 (15)	0.39192 (11)	1.04424 (17)	0.0719 (5)
H9	1.0205	0.4388	1.0682	0.086*
C10	0.99010 (14)	0.35617 (12)	0.94293 (16)	0.0742 (5)
H10	1.0304	0.3791	0.8975	0.089*
C11	0.93693 (14)	0.28622 (11)	0.90749 (15)	0.0670 (5)
H11	0.9425	0.2616	0.8392	0.080*
C12	0.87536 (12)	0.25291 (9)	0.97371 (13)	0.0531 (4)
C13	0.73979 (12)	0.18623 (9)	0.82857 (12)	0.0521 (4)
C14	0.69523 (13)	0.25939 (9)	0.78731 (13)	0.0543 (4)
H14	0.7134	0.3051	0.8321	0.065*
C15	0.62532 (12)	0.26470 (9)	0.68204 (14)	0.0532 (4)
H15	0.5975	0.3143	0.6563	0.064*
C16	0.59430 (11)	0.19754 (9)	0.61181 (13)	0.0504 (4)
C17	0.63661 (12)	0.12448 (10)	0.65608 (13)	0.0571 (4)
H17	0.6158	0.0784	0.6131	0.069*
C18	0.70818 (13)	0.11848 (10)	0.76140 (14)	0.0578 (4)
H18	0.7355	0.0689	0.7878	0.069*
C19	0.52268 (12)	0.20214 (10)	0.49796 (13)	0.0533 (4)
H19	0.4978	0.1541	0.4626	0.064*
C20	0.48912 (12)	0.26930 (10)	0.43923 (14)	0.0552 (4)
H20	0.5141	0.3171	0.4753	0.066*
C21	0.41880 (11)	0.27527 (9)	0.32670 (13)	0.0501 (4)
C22	0.40255 (12)	0.34749 (9)	0.27357 (13)	0.0549 (4)
H22	0.4357	0.3918	0.3131	0.066*
C23	0.33747 (12)	0.35870 (9)	0.16069 (13)	0.0512 (4)
C24	0.28127 (13)	0.28808 (9)	0.09855 (13)	0.0561 (4)
H24A	0.3210	0.2671	0.0465	0.067*
H24B	0.2144	0.3056	0.0515	0.067*
C25	0.26297 (12)	0.22075 (9)	0.17857 (13)	0.0520 (4)
C26	0.36565 (12)	0.20259 (9)	0.26656 (14)	0.0545 (4)
H26A	0.3521	0.1660	0.3243	0.065*
H26B	0.4123	0.1761	0.2269	0.065*
C27	0.17984 (13)	0.24505 (11)	0.24035 (16)	0.0686 (5)
H27A	0.1163	0.2569	0.1840	0.103*
H27B	0.2026	0.2915	0.2869	0.103*
H27C	0.1681	0.2021	0.2891	0.103*
C28	0.22779 (15)	0.14665 (11)	0.10523 (16)	0.0787 (6)
H28A	0.2813	0.1307	0.0679	0.118*
H28B	0.1651	0.1584	0.0475	0.118*
H28C	0.2148	0.1042	0.1541	0.118*
C29	0.32897 (13)	0.43195 (9)	0.10715 (14)	0.0590 (4)
C30	0.38730 (16)	0.49914 (11)	0.16151 (17)	0.0730 (5)
C31	0.26565 (15)	0.44413 (10)	−0.00723 (17)	0.0649 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0691 (9)	0.0547 (8)	0.0565 (8)	−0.0110 (7)	−0.0001 (7)	0.0077 (6)
N2	0.1275 (16)	0.0607 (11)	0.1231 (15)	−0.0240 (11)	0.0169 (12)	−0.0041 (10)
N3	0.1009 (13)	0.0683 (11)	0.0790 (11)	−0.0048 (9)	0.0118 (9)	0.0167 (8)
C1	0.141 (2)	0.0771 (15)	0.0818 (15)	−0.0301 (15)	0.0420 (15)	0.0037 (11)
C2	0.190 (3)	0.0671 (15)	0.0774 (15)	−0.0170 (18)	−0.0100 (18)	0.0142 (11)
C3	0.133 (2)	0.0778 (16)	0.122 (2)	−0.0014 (16)	−0.0367 (17)	0.0290 (15)
C4	0.0822 (14)	0.0771 (14)	0.1062 (16)	−0.0069 (11)	−0.0110 (12)	0.0232 (12)
C5	0.0716 (11)	0.0487 (9)	0.0526 (9)	−0.0029 (8)	0.0101 (8)	0.0012 (7)
C6	0.0856 (13)	0.0656 (12)	0.0772 (12)	−0.0033 (10)	0.0315 (10)	0.0035 (9)
C7	0.0588 (10)	0.0628 (11)	0.0595 (9)	−0.0036 (8)	0.0162 (8)	0.0009 (8)
C8	0.0745 (12)	0.0604 (11)	0.0696 (11)	0.0016 (9)	0.0112 (9)	−0.0073 (8)
C9	0.0724 (12)	0.0521 (10)	0.0809 (12)	−0.0102 (9)	−0.0011 (9)	0.0066 (9)
C10	0.0684 (12)	0.0802 (13)	0.0709 (12)	−0.0198 (10)	0.0111 (9)	0.0164 (10)
C11	0.0672 (11)	0.0787 (12)	0.0552 (9)	−0.0115 (9)	0.0149 (8)	0.0008 (8)
C12	0.0512 (9)	0.0529 (9)	0.0517 (8)	−0.0048 (7)	0.0059 (7)	0.0057 (7)
C13	0.0522 (9)	0.0521 (9)	0.0507 (8)	−0.0033 (7)	0.0099 (7)	0.0008 (7)
C14	0.0576 (9)	0.0484 (9)	0.0559 (9)	−0.0010 (7)	0.0117 (7)	−0.0049 (7)
C15	0.0517 (9)	0.0481 (9)	0.0597 (9)	0.0047 (7)	0.0132 (7)	0.0000 (7)
C16	0.0429 (8)	0.0542 (9)	0.0544 (9)	0.0022 (7)	0.0126 (6)	−0.0010 (7)
C17	0.0558 (9)	0.0525 (10)	0.0606 (9)	−0.0009 (8)	0.0092 (7)	−0.0085 (7)
C18	0.0595 (10)	0.0469 (9)	0.0635 (10)	0.0054 (7)	0.0080 (8)	0.0017 (7)
C19	0.0437 (8)	0.0570 (10)	0.0589 (9)	−0.0002 (7)	0.0118 (7)	−0.0057 (7)
C20	0.0462 (9)	0.0565 (10)	0.0612 (9)	−0.0058 (7)	0.0098 (7)	−0.0016 (7)
C21	0.0413 (8)	0.0512 (9)	0.0588 (9)	−0.0006 (7)	0.0141 (7)	−0.0009 (7)
C22	0.0528 (9)	0.0501 (9)	0.0619 (9)	−0.0073 (7)	0.0139 (7)	−0.0040 (7)
C23	0.0491 (8)	0.0484 (9)	0.0592 (9)	−0.0017 (7)	0.0193 (7)	−0.0003 (7)
C24	0.0558 (9)	0.0552 (10)	0.0573 (9)	−0.0034 (7)	0.0135 (7)	−0.0001 (7)
C25	0.0471 (8)	0.0459 (8)	0.0597 (9)	−0.0019 (7)	0.0068 (7)	0.0021 (7)
C26	0.0476 (8)	0.0490 (9)	0.0646 (9)	0.0025 (7)	0.0089 (7)	−0.0003 (7)
C27	0.0488 (9)	0.0758 (12)	0.0828 (12)	−0.0002 (8)	0.0192 (8)	0.0162 (9)
C28	0.0809 (13)	0.0588 (11)	0.0841 (13)	−0.0143 (9)	−0.0039 (10)	−0.0047 (9)
C29	0.0636 (10)	0.0501 (9)	0.0652 (10)	−0.0030 (8)	0.0189 (8)	0.0023 (7)
C30	0.0869 (14)	0.0490 (10)	0.0813 (12)	−0.0072 (10)	0.0173 (10)	0.0056 (9)
C31	0.0738 (12)	0.0497 (10)	0.0730 (12)	−0.0035 (9)	0.0215 (9)	0.0079 (8)

N1—C13	1.405 (2)	C15—H15	0.9300
N1—C5	1.418 (2)	C16—C17	1.395 (2)
N1—C12	1.431 (2)	C16—C19	1.453 (2)
N2—C30	1.141 (2)	C17—C18	1.378 (2)
N3—C31	1.143 (2)	C17—H17	0.9300
C1—C2	1.354 (4)	C18—H18	0.9300
C1—C6	1.392 (3)	C19—C20	1.342 (2)
C1—H1	0.9300	C19—H19	0.9300
C2—C3	1.347 (4)	C20—C21	1.435 (2)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.375 (3)	C21—C22	1.358 (2)
C3—H3	0.9300	C21—C26	1.498 (2)
C4—C5	1.374 (3)	C22—C23	1.420 (2)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.374 (2)	C23—C29	1.375 (2)
C6—H6	0.9300	C23—C24	1.494 (2)
C7—C8	1.373 (2)	C24—C25	1.533 (2)
C7—C12	1.375 (2)	C24—H24A	0.9700
C7—H7	0.9300	C24—H24B	0.9700
C8—C9	1.373 (3)	C25—C27	1.520 (2)
C8—H8	0.9300	C25—C28	1.524 (2)
C9—C10	1.365 (3)	C25—C26	1.531 (2)
C9—H9	0.9300	C26—H26A	0.9700
C10—C11	1.379 (2)	C26—H26B	0.9700
C10—H10	0.9300	C27—H27A	0.9600
C11—C12	1.381 (2)	C27—H27B	0.9600
C11—H11	0.9300	C27—H27C	0.9600
C13—C18	1.392 (2)	C28—H28A	0.9600
C13—C14	1.397 (2)	C28—H28B	0.9600
C14—C15	1.366 (2)	C28—H28C	0.9600
C14—H14	0.9300	C29—C31	1.428 (3)
C15—C16	1.402 (2)	C29—C30	1.428 (3)
C13—N1—C5	122.75 (13)	C17—C18—C13	120.40 (15)
C13—N1—C12	118.53 (12)	C17—C18—H18	119.8
C5—N1—C12	118.29 (13)	C13—C18—H18	119.8
C2—C1—C6	121.1 (2)	C20—C19—C16	125.98 (15)
C2—C1—H1	119.4	C20—C19—H19	117.0
C6—C1—H1	119.4	C16—C19—H19	117.0
C3—C2—C1	119.4 (2)	C19—C20—C21	126.94 (15)
C3—C2—H2	120.3	C19—C20—H20	116.5
C1—C2—H2	120.3	C21—C20—H20	116.5
C2—C3—C4	120.8 (2)	C22—C21—C20	119.28 (14)
C2—C3—H3	119.6	C22—C21—C26	119.98 (14)
C4—C3—H3	119.6	C20—C21—C26	120.72 (14)
C5—C4—C3	120.8 (2)	C21—C22—C23	123.27 (14)
C5—C4—H4	119.6	C21—C22—H22	118.4
C3—C4—H4	119.6	C23—C22—H22	118.4
C4—C5—C6	118.46 (17)	C29—C23—C22	121.22 (14)
C4—C5—N1	119.87 (17)	C29—C23—C24	120.23 (14)
C6—C5—N1	121.62 (16)	C22—C23—C24	118.50 (13)
C5—C6—C1	119.5 (2)	C23—C24—C25	114.28 (13)
C5—C6—H6	120.3	C23—C24—H24A	108.7
C1—C6—H6	120.3	C25—C24—H24A	108.7
C8—C7—C12	120.24 (16)	C23—C24—H24B	108.7
C8—C7—H7	119.9	C25—C24—H24B	108.7
C12—C7—H7	119.9	H24A—C24—H24B	107.6
C9—C8—C7	120.29 (17)	C27—C25—C28	109.77 (14)
C9—C8—H8	119.9	C27—C25—C26	110.51 (14)
C7—C8—H8	119.9	C28—C25—C26	109.03 (13)
C10—C9—C8	119.75 (17)	C27—C25—C24	110.18 (13)
C10—C9—H9	120.1	C28—C25—C24	108.51 (13)
C8—C9—H9	120.1	C26—C25—C24	108.80 (13)
C9—C10—C11	120.45 (17)	C21—C26—C25	113.60 (12)
C9—C10—H10	119.8	C21—C26—H26A	108.8
C11—C10—H10	119.8	C25—C26—H26A	108.8
C10—C11—C12	119.83 (17)	C21—C26—H26B	108.8
C10—C11—H11	120.1	C25—C26—H26B	108.8
C12—C11—H11	120.1	H26A—C26—H26B	107.7
C7—C12—C11	119.43 (15)	C25—C27—H27A	109.5
C7—C12—N1	120.57 (14)	C25—C27—H27B	109.5
C11—C12—N1	119.96 (14)	H27A—C27—H27B	109.5
C18—C13—C14	118.16 (14)	C25—C27—H27C	109.5
C18—C13—N1	121.87 (14)	H27A—C27—H27C	109.5
C14—C13—N1	119.96 (14)	H27B—C27—H27C	109.5
C15—C14—C13	120.86 (14)	C25—C28—H28A	109.5
C15—C14—H14	119.6	C25—C28—H28B	109.5
C13—C14—H14	119.6	H28A—C28—H28B	109.5
C14—C15—C16	121.88 (14)	C25—C28—H28C	109.5
C14—C15—H15	119.1	H28A—C28—H28C	109.5
C16—C15—H15	119.1	H28B—C28—H28C	109.5
C17—C16—C15	116.57 (14)	C23—C29—C31	122.11 (15)
C17—C16—C19	120.59 (14)	C23—C29—C30	121.35 (15)
C15—C16—C19	122.84 (14)	C31—C29—C30	116.48 (15)
C18—C17—C16	122.08 (15)	N2—C30—C29	178.8 (2)
C18—C17—H17	119.0	N3—C31—C29	179.1 (2)
C16—C17—H17	119.0
C6—C1—C2—C3	−0.5 (4)	C14—C15—C16—C17	1.5 (2)
C1—C2—C3—C4	−0.1 (4)	C14—C15—C16—C19	−177.95 (14)
C2—C3—C4—C5	0.2 (4)	C15—C16—C17—C18	−2.3 (2)
C3—C4—C5—C6	0.2 (3)	C19—C16—C17—C18	177.10 (14)
C3—C4—C5—N1	177.9 (2)	C16—C17—C18—C13	0.9 (2)
C13—N1—C5—C4	144.71 (18)	C14—C13—C18—C17	1.4 (2)
C12—N1—C5—C4	−42.9 (2)	N1—C13—C18—C17	−177.36 (14)
C13—N1—C5—C6	−37.7 (2)	C17—C16—C19—C20	−169.57 (15)
C12—N1—C5—C6	134.71 (17)	C15—C16—C19—C20	9.8 (2)
C4—C5—C6—C1	−0.7 (3)	C16—C19—C20—C21	179.76 (14)
N1—C5—C6—C1	−178.40 (17)	C19—C20—C21—C22	−172.13 (15)
C2—C1—C6—C5	0.9 (3)	C19—C20—C21—C26	6.3 (2)
C12—C7—C8—C9	0.0 (3)	C20—C21—C22—C23	177.62 (13)
C7—C8—C9—C10	0.1 (3)	C26—C21—C22—C23	−0.8 (2)
C8—C9—C10—C11	−0.7 (3)	C21—C22—C23—C29	−175.45 (14)
C9—C10—C11—C12	1.3 (3)	C21—C22—C23—C24	2.0 (2)
C8—C7—C12—C11	0.5 (3)	C29—C23—C24—C25	−158.00 (14)
C8—C7—C12—N1	−177.28 (15)	C22—C23—C24—C25	24.5 (2)
C10—C11—C12—C7	−1.2 (3)	C23—C24—C25—C27	72.25 (18)
C10—C11—C12—N1	176.63 (15)	C23—C24—C25—C28	−167.55 (13)
C13—N1—C12—C7	116.95 (17)	C23—C24—C25—C26	−49.05 (18)
C5—N1—C12—C7	−55.8 (2)	C22—C21—C26—C25	−26.7 (2)
C13—N1—C12—C11	−60.8 (2)	C20—C21—C26—C25	154.85 (14)
C5—N1—C12—C11	126.46 (17)	C27—C25—C26—C21	−71.15 (17)
C5—N1—C13—C18	−33.5 (2)	C28—C25—C26—C21	168.12 (13)
C12—N1—C13—C18	154.15 (15)	C24—C25—C26—C21	49.95 (18)
C5—N1—C13—C14	147.73 (15)	C22—C23—C29—C31	178.69 (14)
C12—N1—C13—C14	−24.6 (2)	C24—C23—C29—C31	1.2 (2)
C18—C13—C14—C15	−2.3 (2)	C22—C23—C29—C30	1.7 (2)
N1—C13—C14—C15	176.54 (14)	C24—C23—C29—C30	−175.73 (15)
C13—C14—C15—C16	0.8 (2)