2-{3-Cyano-4-[2-(4-diethylamino-2-hy-droxyphenyl)ethenyl]-5,5-dimethyl-2,5-dihydrofuran-2-ylidene}malononitrile acetone 0.25-solvate.

In the title compound, C(22)H(22)N(4)O(2)·0.25C(3)H(6)O, the disordered acetone mol-ecule lies with partial occupancy about the 2 axis. The mol-ecule of the malononitrile derivative is essentially planar excluding the methyl groups, with the largest deviation from the mean plane through the non-H atoms being 0.1955 (13) Å. Two rotamers with different orientations of the benzene ring are observed in the ratio of 0.919 (2):0.081 (2), and as a result the OH group is disordered over two sets of sites. In the crystal, the mol-ecules form ribbons along (101) utilizing a strong O-H⋯N(cyano) hydrogen bond. Inter-leaving of the nearly planar ribbons is provided by the twofold disordered acetone molecule through C-H⋯O inter-actions.

Related literature

For organic push–pull conjugated molecules in electro-optical applications, see: Dalton (2004 ▶); Ma et al. (2002 ▶); Marder et al. (1997 ▶); Li et al. (2007 ▶); Avetisyan et al. (2009 ▶); Gainsford et al. (2008 ▶). For related structures, see: Li et al. (2009 ▶); Wu et al. (2012 ▶). For the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

4C22H22N4O2·C3H6O

M = 1555.82

Monoclinic,

a = 18.6899 (6) Å

b = 14.4941 (4) Å

c = 16.7485 (5) Å

β = 95.266 (2)°

V = 4517.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.61 × 0.53 × 0.33 mm

Data collection

Bruker-Nonius APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Blessing, 1995 ▶) T min = 0.678, T max = 0.746

51842 measured reflections

6086 independent reflections

4957 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.138

S = 1.04

6089 reflections

289 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT and SADABS (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039736/yk2072sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039736/yk2072Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039736/yk2072Isup3.cml

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

4C22H22N4O2·C3H6O	F(000) = 1648
Mr = 1555.82	Dx = 1.144 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9270 reflections
a = 18.6899 (6) Å	θ = 2.2–29.2°
b = 14.4941 (4) Å	µ = 0.08 mm−1
c = 16.7485 (5) Å	T = 113 K
β = 95.266 (2)°	Block, violet
V = 4517.9 (2) Å3	0.61 × 0.53 × 0.33 mm
Z = 2

Bruker-Nonius APEXII CCD diffractometer	6086 independent reflections
Radiation source: fine-focus sealed tube	4957 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 8.333 pixels mm-1	θmax = 29.3°, θmin = 2.4°
φ and ω scans	h = −25→25
Absorption correction: multi-scan (SADABS; Blessing, 1995)	k = −19→19
Tmin = 0.678, Tmax = 0.746	l = −22→23
51842 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0684P)2 + 3.4092P] where P = (Fo2 + 2Fc2)/3
6089 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.44 e Å−3
5 restraints	Δρmin = −0.34 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	Occ. (<1)
O1	0.61544 (5)	−0.22668 (6)	0.49734 (5)	0.02549 (19)
N1	0.74054 (7)	−0.33495 (9)	0.63481 (7)	0.0354 (3)
N2	0.81037 (8)	−0.05230 (10)	0.62647 (10)	0.0519 (4)
N4	0.28556 (6)	0.21599 (9)	0.17128 (7)	0.0337 (3)
N3	0.67592 (6)	0.09283 (8)	0.51591 (7)	0.0342 (3)
C1	0.72855 (6)	−0.26329 (9)	0.60753 (7)	0.0263 (2)
C2	0.71622 (6)	−0.17294 (9)	0.57628 (7)	0.0238 (2)
C3	0.76699 (7)	−0.10418 (10)	0.60298 (8)	0.0318 (3)
C4	0.56689 (6)	−0.09065 (8)	0.43879 (6)	0.0200 (2)
C5	0.62913 (6)	−0.07176 (8)	0.48837 (6)	0.0204 (2)
C6	0.65688 (6)	−0.15572 (8)	0.52307 (6)	0.0211 (2)
C7	0.55438 (6)	−0.19392 (8)	0.44206 (7)	0.0216 (2)
C8	0.56100 (7)	−0.24283 (9)	0.36256 (7)	0.0285 (3)
H8A	0.5624	−0.3097	0.3713	0.043*
H8B	0.6053	−0.2231	0.3405	0.043*
H8C	0.5196	−0.2272	0.3248	0.043*
C9	0.48701 (7)	−0.22100 (9)	0.48084 (8)	0.0286 (3)
H9A	0.4870	−0.1905	0.5331	0.043*
H9B	0.4862	−0.2881	0.4882	0.043*
H9C	0.4445	−0.2019	0.4463	0.043*
C10	0.65681 (6)	0.01838 (8)	0.50443 (7)	0.0237 (2)
C11	0.52475 (6)	−0.02424 (8)	0.39539 (6)	0.0215 (2)
H11	0.5409	0.0379	0.3989	0.026*
C12	0.46183 (6)	−0.04148 (8)	0.34801 (6)	0.0206 (2)
H12	0.4463	−0.1038	0.3441	0.025*
C13	0.41816 (6)	0.02472 (8)	0.30455 (6)	0.0198 (2)
C14	0.35532 (6)	−0.00359 (8)	0.25653 (7)	0.0229 (2)
H14	0.3431	−0.0672	0.2544	0.027*	0.081 (2)
O2A	0.34030 (5)	−0.09416 (7)	0.25497 (6)	0.0295 (3)	0.919 (2)
H2A	0.3035 (10)	−0.1063 (13)	0.2199 (11)	0.035*	0.919 (2)
C15	0.31146 (6)	0.05859 (9)	0.21287 (7)	0.0273 (3)
H15	0.2696	0.0371	0.1820	0.033*
C16	0.32793 (7)	0.15364 (9)	0.21348 (7)	0.0268 (3)
C17	0.39137 (7)	0.18304 (9)	0.26073 (7)	0.0270 (2)
H17	0.4044	0.2464	0.2620	0.032*
C18	0.43327 (6)	0.12048 (8)	0.30389 (7)	0.0230 (2)
H18	0.4748	0.1422	0.3352	0.028*	0.919 (2)
O2B	0.4814 (5)	0.1629 (7)	0.3528 (6)	0.0295 (3)	0.081 (2)
H2B	0.5066 (16)	0.203 (3)	0.333 (3)	0.035*	0.081 (2)
C19	0.22046 (8)	0.18697 (11)	0.12259 (8)	0.0385 (3)
H19A	0.2297	0.1275	0.0963	0.046*
H19B	0.2085	0.2333	0.0800	0.046*
C20	0.15686 (8)	0.17596 (13)	0.17183 (11)	0.0464 (4)
H20A	0.1459	0.2354	0.1958	0.070*
H20B	0.1685	0.1306	0.2144	0.070*
H20C	0.1150	0.1548	0.1371	0.070*
C21	0.30658 (8)	0.31313 (10)	0.16457 (9)	0.0357 (3)
H21A	0.3280	0.3353	0.2174	0.043*
H21B	0.2634	0.3508	0.1490	0.043*
C22	0.36029 (10)	0.32545 (13)	0.10298 (10)	0.0483 (4)
H22A	0.3407	0.2992	0.0517	0.072*
H22B	0.4052	0.2938	0.1213	0.072*
H22C	0.3698	0.3913	0.0962	0.072*
O3	0.4975 (9)	0.3578 (3)	0.2641 (9)	0.086 (2)	0.25
C23	0.5000	0.5166 (6)	0.2500	0.105 (3)	0.50
H23A	0.5191	0.5035	0.1986	0.158*	0.25
H23B	0.5359	0.5507	0.2847	0.158*	0.25
H23C	0.4562	0.5537	0.2408	0.158*	0.25
C24	0.4839 (5)	0.4325 (6)	0.2875 (7)	0.086 (2)	0.25
C25	0.4474 (5)	0.4443 (6)	0.3616 (8)	0.086 (2)	0.25
H25A	0.4438	0.3845	0.3882	0.129*	0.25
H25B	0.3991	0.4693	0.3480	0.129*	0.25
H25C	0.4751	0.4871	0.3977	0.129*	0.25

	U11	U22	U33	U12	U13	U23
O1	0.0254 (4)	0.0211 (4)	0.0284 (4)	0.0027 (3)	−0.0068 (3)	0.0028 (3)
N1	0.0359 (6)	0.0361 (6)	0.0331 (6)	0.0097 (5)	−0.0033 (5)	0.0076 (5)
N2	0.0411 (7)	0.0437 (8)	0.0659 (9)	−0.0064 (6)	−0.0213 (7)	0.0056 (7)
N4	0.0316 (6)	0.0376 (6)	0.0307 (5)	0.0118 (5)	−0.0044 (4)	0.0062 (5)
N3	0.0336 (6)	0.0286 (6)	0.0386 (6)	−0.0030 (5)	−0.0059 (5)	−0.0012 (5)
C1	0.0230 (5)	0.0330 (6)	0.0222 (5)	0.0067 (5)	−0.0020 (4)	0.0023 (5)
C2	0.0210 (5)	0.0278 (6)	0.0219 (5)	0.0045 (4)	−0.0020 (4)	0.0028 (4)
C3	0.0266 (6)	0.0335 (7)	0.0335 (6)	0.0049 (5)	−0.0076 (5)	0.0047 (5)
C4	0.0189 (5)	0.0216 (5)	0.0191 (5)	0.0020 (4)	−0.0009 (4)	0.0001 (4)
C5	0.0185 (5)	0.0218 (5)	0.0202 (5)	0.0024 (4)	−0.0021 (4)	0.0008 (4)
C6	0.0201 (5)	0.0231 (5)	0.0200 (5)	0.0033 (4)	0.0003 (4)	0.0008 (4)
C7	0.0200 (5)	0.0212 (5)	0.0226 (5)	0.0021 (4)	−0.0042 (4)	0.0009 (4)
C8	0.0305 (6)	0.0272 (6)	0.0270 (6)	0.0031 (5)	−0.0021 (5)	−0.0051 (5)
C9	0.0260 (6)	0.0282 (6)	0.0315 (6)	−0.0025 (5)	0.0020 (5)	0.0026 (5)
C10	0.0203 (5)	0.0267 (6)	0.0230 (5)	0.0024 (4)	−0.0033 (4)	0.0012 (4)
C11	0.0210 (5)	0.0215 (5)	0.0212 (5)	0.0022 (4)	−0.0020 (4)	0.0008 (4)
C12	0.0204 (5)	0.0218 (5)	0.0191 (5)	0.0021 (4)	−0.0010 (4)	0.0006 (4)
C13	0.0179 (5)	0.0234 (5)	0.0177 (5)	0.0030 (4)	−0.0011 (4)	−0.0005 (4)
C14	0.0206 (5)	0.0259 (6)	0.0216 (5)	0.0020 (4)	−0.0018 (4)	−0.0032 (4)
O2A	0.0274 (5)	0.0231 (5)	0.0354 (5)	−0.0005 (4)	−0.0115 (4)	−0.0025 (4)
C15	0.0207 (5)	0.0362 (7)	0.0235 (5)	0.0049 (5)	−0.0051 (4)	−0.0025 (5)
C16	0.0254 (6)	0.0329 (6)	0.0218 (5)	0.0095 (5)	−0.0001 (4)	0.0028 (4)
C17	0.0287 (6)	0.0252 (6)	0.0266 (6)	0.0036 (5)	0.0005 (5)	0.0030 (4)
C18	0.0225 (5)	0.0257 (6)	0.0200 (5)	0.0005 (4)	−0.0021 (4)	0.0003 (4)
O2B	0.0274 (5)	0.0231 (5)	0.0354 (5)	−0.0005 (4)	−0.0115 (4)	−0.0025 (4)
C19	0.0359 (7)	0.0457 (8)	0.0311 (6)	0.0147 (6)	−0.0121 (5)	0.0016 (6)
C20	0.0317 (7)	0.0537 (10)	0.0517 (9)	0.0122 (7)	−0.0083 (6)	−0.0029 (7)
C21	0.0402 (7)	0.0335 (7)	0.0332 (6)	0.0157 (6)	0.0025 (6)	0.0065 (5)
C22	0.0616 (11)	0.0467 (9)	0.0381 (8)	0.0144 (8)	0.0131 (7)	0.0114 (7)
O3	0.057 (3)	0.0470 (19)	0.148 (7)	0.013 (2)	−0.023 (4)	−0.023 (3)
C23	0.120 (7)	0.066 (5)	0.131 (8)	0.000	0.016 (6)	0.000
C24	0.057 (3)	0.0470 (19)	0.148 (7)	0.013 (2)	−0.023 (4)	−0.023 (3)
C25	0.057 (3)	0.0470 (19)	0.148 (7)	0.013 (2)	−0.023 (4)	−0.023 (3)

O1—C6	1.3351 (14)	O2A—H2A	0.88 (2)
O1—C7	1.4802 (13)	C15—C16	1.4116 (19)
N1—C1	1.1484 (17)	C15—H15	0.9500
N2—C3	1.1485 (19)	C16—C17	1.4286 (18)
N4—C16	1.3567 (15)	C17—C18	1.3617 (16)
N4—C19	1.4630 (18)	C17—H17	0.9500
N4—C21	1.469 (2)	C18—O2B	1.313 (5)
N3—C10	1.1473 (17)	C18—H18	0.9500
C1—C2	1.4212 (17)	O2B—H2B	0.840 (10)
C2—C6	1.3803 (15)	C19—C20	1.516 (2)
C2—C3	1.4198 (18)	C19—H19A	0.9900
C4—C5	1.3929 (15)	C19—H19B	0.9900
C4—C11	1.4037 (15)	C20—H20A	0.9800
C4—C7	1.5167 (16)	C20—H20B	0.9800
C5—C10	1.4218 (16)	C20—H20C	0.9800
C5—C6	1.4256 (15)	C21—C22	1.514 (2)
C7—C9	1.5203 (17)	C21—H21A	0.9900
C7—C8	1.5235 (16)	C21—H21B	0.9900
C8—H8A	0.9800	C22—H22A	0.9800
C8—H8B	0.9800	C22—H22B	0.9800
C8—H8C	0.9800	C22—H22C	0.9800
C9—H9A	0.9800	O3—C24	1.187 (11)
C9—H9B	0.9800	C23—C24	1.416 (10)
C9—H9C	0.9800	C23—H23A	0.9800
C11—C12	1.3798 (15)	C23—H23B	0.9800
C11—H11	0.9500	C23—H23C	0.9800
C12—C13	1.4169 (15)	C24—C24i	1.44 (2)
C12—H12	0.9500	C24—O3i	1.447 (14)
C13—C18	1.4166 (16)	C24—C25	1.480 (12)
C13—C14	1.4216 (15)	C25—H25A	0.9800
C14—C15	1.3816 (16)	C25—H25B	0.9800
C14—H14	0.9500	C25—H25C	0.9800
C14—O2A	1.3422 (15)
C6—O1—C7	110.24 (8)	C16—C17—H17	119.9
C16—N4—C19	120.99 (12)	O2B—C18—C17	110.3 (5)
C16—N4—C21	122.06 (12)	O2B—C18—C13	125.4 (5)
C19—N4—C21	116.58 (11)	C17—C18—C13	123.45 (11)
N1—C1—C2	177.39 (14)	C17—C18—H18	118.3
C6—C2—C3	123.41 (11)	C13—C18—H18	118.3
C6—C2—C1	119.87 (11)	C18—O2B—H2B	117 (3)
C3—C2—C1	116.72 (10)	N4—C19—C20	112.37 (12)
N2—C3—C2	176.28 (15)	N4—C19—H19A	109.1
C5—C4—C11	124.90 (11)	C20—C19—H19A	109.1
C5—C4—C7	107.19 (9)	N4—C19—H19B	109.1
C11—C4—C7	127.91 (10)	C20—C19—H19B	109.1
C4—C5—C10	124.25 (10)	H19A—C19—H19B	107.9
C4—C5—C6	109.15 (10)	C19—C20—H20A	109.5
C10—C5—C6	126.50 (10)	C19—C20—H20B	109.5
O1—C6—C2	118.49 (10)	H20A—C20—H20B	109.5
O1—C6—C5	110.33 (9)	C19—C20—H20C	109.5
C2—C6—C5	131.18 (11)	H20A—C20—H20C	109.5
O1—C7—C4	103.09 (8)	H20B—C20—H20C	109.5
O1—C7—C9	105.73 (9)	N4—C21—C22	111.34 (12)
C4—C7—C9	114.00 (10)	N4—C21—H21A	109.4
O1—C7—C8	106.11 (9)	C22—C21—H21A	109.4
C4—C7—C8	113.73 (10)	N4—C21—H21B	109.4
C9—C7—C8	112.97 (10)	C22—C21—H21B	109.4
N3—C10—C5	176.62 (13)	H21A—C21—H21B	108.0
C12—C11—C4	125.57 (11)	C21—C22—H22A	109.5
C12—C11—H11	117.2	C21—C22—H22B	109.5
C4—C11—H11	117.2	H22A—C22—H22B	109.5
C11—C12—C13	126.38 (11)	C21—C22—H22C	109.5
C11—C12—H12	116.8	H22A—C22—H22C	109.5
C13—C12—H12	116.8	H22B—C22—H22C	109.5
C18—C13—C12	124.17 (10)	C24—C23—H23A	109.5
C18—C13—C14	115.68 (10)	C24—C23—H23B	109.5
C12—C13—C14	120.15 (10)	H23A—C23—H23B	109.5
O2A—C14—C13	116.99 (10)	C24—C23—H23C	109.5
O2A—C14—C15	120.99 (11)	H23A—C23—H23C	109.5
C14—O2A—H2A	111.0 (12)	H23B—C23—H23C	109.5
C15—C14—C13	122.04 (11)	O3—C24—C23	125.3 (11)
C15—C14—H14	119.0	C23—C24—O3i	107.9 (8)
C13—C14—H14	119.0	O3—C24—C25	120.8 (11)
C14—C15—C16	120.95 (11)	C23—C24—C25	113.9 (7)
C14—C15—H15	119.5	O3i—C24—C25	137.9 (8)
C16—C15—H15	119.5	C24—C25—H25A	109.5
N4—C16—C15	121.99 (12)	C24—C25—H25B	109.5
N4—C16—C17	120.33 (12)	H25A—C25—H25B	109.5
C15—C16—C17	117.68 (11)	C24—C25—H25C	109.5
C18—C17—C16	120.20 (12)	H25A—C25—H25C	109.5
C18—C17—H17	119.9	H25B—C25—H25C	109.5
C11—C4—C5—C10	2.82 (18)	C4—C11—C12—C13	179.20 (11)
C7—C4—C5—C10	−176.69 (11)	C11—C12—C13—C18	−0.24 (19)
C11—C4—C5—C6	179.34 (10)	C11—C12—C13—C14	178.55 (11)
C7—C4—C5—C6	−0.17 (13)	C18—C13—C14—C15	−0.75 (17)
C7—O1—C6—C2	179.11 (10)	C12—C13—C14—C15	−179.65 (11)
C7—O1—C6—C5	−0.50 (13)	C13—C14—C15—C16	0.76 (18)
C3—C2—C6—O1	175.13 (11)	C19—N4—C16—C15	−0.26 (19)
C1—C2—C6—O1	−5.26 (17)	C21—N4—C16—C15	−173.06 (12)
C3—C2—C6—C5	−5.4 (2)	C19—N4—C16—C17	179.96 (12)
C1—C2—C6—C5	174.26 (12)	C21—N4—C16—C17	7.15 (19)
C4—C5—C6—O1	0.42 (13)	C14—C15—C16—N4	−179.80 (12)
C10—C5—C6—O1	176.85 (11)	C14—C15—C16—C17	−0.02 (18)
C4—C5—C6—C2	−179.12 (12)	N4—C16—C17—C18	179.09 (12)
C10—C5—C6—C2	−2.7 (2)	C15—C16—C17—C18	−0.70 (18)
C6—O1—C7—C4	0.37 (12)	C16—C17—C18—O2B	−169.5 (6)
C6—O1—C7—C9	−119.59 (10)	C16—C17—C18—C13	0.70 (19)
C6—O1—C7—C8	120.19 (10)	C12—C13—C18—O2B	−12.4 (7)
C5—C4—C7—O1	−0.10 (12)	C14—C13—C18—O2B	168.7 (7)
C11—C4—C7—O1	−179.60 (11)	C12—C13—C18—C17	178.87 (11)
C5—C4—C7—C9	113.99 (11)	C14—C13—C18—C17	0.02 (17)
C11—C4—C7—C9	−65.50 (15)	C16—N4—C19—C20	82.75 (17)
C5—C4—C7—C8	−114.53 (11)	C21—N4—C19—C20	−104.06 (15)
C11—C4—C7—C8	65.98 (15)	C16—N4—C21—C22	78.93 (17)
C5—C4—C11—C12	−177.89 (11)	C19—N4—C21—C22	−94.18 (15)
C7—C4—C11—C12	1.52 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2OA···N1ii	0.88 (2)	1.96 (2)	2.8095 (16)	162 (2)
C17—H17···O3	0.95	2.37	3.213 (13)	148
C17—H17···O3i	0.95	2.51	3.324 (13)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H2OA⋯N1i	0.88 (2)	1.96 (2)	2.8095 (16)	162 (2)
C17—H17⋯O3	0.95	2.37	3.213 (13)	148
C17—H17⋯O3ii	0.95	2.51	3.324 (13)	144

Symmetry codes: (i) ; (ii) .