2-{3-Cyano-5,5-dimethyl-4-[4-(pyrrol­idin-1-yl)buta-1,3-dien­yl]-2,5-dihydro­furan-2-yl­idene}malononitrile dichloro­methane solvate

Gainsford, G.J.; Bhuiyan, M.D.H.; Kay, A.J.; Robinson, W.T.

doi:10.1107/S1600536808024719

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1715

doi:10.1107/S1600536808024719

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2-{3-Cyano-5,5-dimethyl-4-[4-(pyrrolidin-1-yl)buta-1,3-dienyl]-2,5-dihydrofuran-2-ylidene}malononitrile dichloromethane solvate

Graeme J. Gainsford,^a ^* M. Delower H. Bhuiyan,^a Andrew J. Kay ^a and Ward T. Robinson ^b

^aIndustrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand, and ^bDepartment of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand
^*Correspondence e-mail: g.gainsford@irl.cri.nz

(Received 15 July 2008; accepted 1 August 2008; online 6 August 2008)

The structure of the title compound, C₁₈H₁₈N₄O·CH₂Cl₂, was solved using data collected from a multiple crystal (note high R factors). The crystal structure is dominated by two bifurcated attractive C—H⋯N(cyano) interactions.

Related literature

For the synthesis, see Kay et al. (2004 ). For background, see Gainsford et al. (2007 , 2008a ,b ,c ).

Experimental

Crystal data

C₁₈H₁₈N₄O·CH₂Cl₂
M_r = 391.29
Monoclinic, P 2₁ /c
a = 6.8755 (8) Å
b = 16.8913 (17) Å
c = 16.6677 (18) Å
β = 93.482 (8)°
V = 1932.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 120 (2) K
0.30 × 0.15 × 0.13 mm

Data collection

Bruker–Nonius APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.570, T_max = 0.955
4280 measured reflections
4280 independent reflections
2517 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.095
wR(F²) = 0.270
S = 0.99
4280 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 1.36 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯N1ⁱ	0.95	2.52	3.378 (5)	150
C18—H18B⋯N1ⁱ	0.99	2.56	3.400 (5)	142
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: RLATT (Bruker, 2004 ), SAINT (Bruker, 2005) and SADABS (Sheldrick, 2003 ); 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 PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024719/lh2664sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024719/lh2664Isup2.hkl

checkCIF report

Comment top

We have previously reported on the synthesis of a number of high figure of merit chromophores for nonlinear optics (Kay et al., 2004), and the X-ray crystallographic and structural properties of crucial dye precursors used (Gainsford et al., 2007, 2008a,b). A closely related compound 2-[3-Cyano-5,5-dimethyl-4-(6-pyrrolidin-1-yl-hexa -1,3,5-trienyl)-5H-furan-2-ylidene]-malononitrile will be reported shortly (Gainsford et al., 2008c).

In the crystal structure, the molecules (Fig. 1) are bound into planar dimer units via a polyene C–H and pyrollidine C–H bifurcated interaction with one cyano nitrogen atom (N1, Table 1). Other very weak intermolecular interactions providing inter-plane or solvent links, such as the one between the dichloromethane H19A and N1 (2.70 Å), are consistent with the difficulty found in obtaining a good single-crystal of this compound.

Related literature top

For the synthesis, see Kay et al. (2004). For background, see Gainsford et al. (2007, 2008a,b,c).

Experimental top

To a solution of 5.8 mmole of {4-(4-Acetanilido-trans-1,3-butadienyl) -3-cyano-5,5-dimethyl-2(5H)-furanylidene}propanedinitrile (Compound 11b, Kay et al., 2004) in 30 ml of ethanol was added an equimolar quantity of pyrrolidine. The solution was refluxed 1 h, cooled and the product collected by filtration and washed with ethanol. λ_max 530 nm (pyridine); 530 nm (DMF) log₁₀ε 5.22. Final crystallization was from a 1:1 dichloromethane/ ethyl acetate mixture.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: RLATT (Bruker, 2004), SAINT (Bruker, 2005) and SADABS (Sheldrick, 2003); 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 PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. Molecular structure of the asymmetic unit (Farrugia, 1997); displacement ellipsoids are shown at the 50% probability level.

2-{3-Cyano-5,5-dimethyl-4-[4-(pyrrolidin-1-yl)buta-1,3-dienyl]-2,5- dihydrofuran-2-ylidene}malononitrile dichloromethane solvate top

Crystal data top

C₁₈H₁₈N₄O·CH₂Cl₂	F(000) = 816
M_r = 391.29	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5595 reflections
a = 6.8755 (8) Å	θ = 2.4–29.2°
b = 16.8913 (17) Å	µ = 0.35 mm⁻¹
c = 16.6677 (18) Å	T = 120 K
β = 93.482 (8)°	Block, red
V = 1932.1 (4) Å³	0.30 × 0.15 × 0.13 mm
Z = 4

Data collection top

Bruker–Nonius APEXII CCD area-detector diffractometer	4280 independent reflections
Radiation source: fine-focus sealed tube	2517 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
Detector resolution: 8.192 pixels mm^-1	θ_max = 29.0°, θ_min = 2.7°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (Blessing, 1995)	k = 0→23
T_min = 0.570, T_max = 0.955	l = 0→22
4280 measured reflections

Refinement top

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)] = 0.095	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.270	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.1824P)²] where P = (F_o² + 2F_c²)/3
4280 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 1.36 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₈H₁₈N₄O·CH₂Cl₂	V = 1932.1 (4) Å³
M_r = 391.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.8755 (8) Å	µ = 0.35 mm⁻¹
b = 16.8913 (17) Å	T = 120 K
c = 16.6677 (18) Å	0.30 × 0.15 × 0.13 mm
β = 93.482 (8)°

Data collection top

Bruker–Nonius APEXII CCD area-detector diffractometer	4280 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	2517 reflections with I > 2σ(I)
T_min = 0.570, T_max = 0.955	R_int = 0.099
4280 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.095	0 restraints
wR(F²) = 0.270	H-atom parameters constrained
S = 0.99	Δρ_max = 1.36 e Å⁻³
4280 reflections	Δρ_min = −0.47 e Å⁻³
237 parameters

Special details top

Experimental. There were 36108 reflections measured in the data collection (43242 of which 7061 were rejected to 2theta 58 degrees & 73 were systematic absence violations)

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. Four low theta angle reflections affected by the backstop were omitted.

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.2744 (2)	0.45770 (7)	0.31788 (7)	0.0405 (4)
Cl2	0.2711 (3)	0.62862 (7)	0.30173 (9)	0.0578 (5)
O1	0.7615 (4)	0.90197 (14)	0.42000 (15)	0.0176 (6)
N1	0.7450 (8)	1.0058 (2)	0.6850 (2)	0.0461 (13)
N2	0.7371 (6)	1.1047 (2)	0.4400 (2)	0.0308 (9)
N3	0.8028 (7)	0.8020 (2)	0.6872 (2)	0.0382 (10)
N4	0.7736 (5)	0.41968 (17)	0.40006 (18)	0.0175 (7)
C1	0.7496 (7)	0.9959 (2)	0.6163 (3)	0.0250 (9)
C2	0.7542 (6)	0.9836 (2)	0.5329 (2)	0.0187 (8)
C3	0.7462 (6)	1.0505 (2)	0.4810 (2)	0.0218 (8)
C4	0.7730 (5)	0.7750 (2)	0.4757 (2)	0.0149 (7)
C5	0.7705 (6)	0.8175 (2)	0.3964 (2)	0.0160 (7)
C6	0.7637 (5)	0.9082 (2)	0.5002 (2)	0.0148 (7)
C7	0.7736 (6)	0.8325 (2)	0.5364 (2)	0.0156 (7)
C8	0.9567 (6)	0.8083 (2)	0.3533 (2)	0.0234 (8)
H8A	0.9604	0.8482	0.3107	0.035*
H8B	0.9611	0.7553	0.3295	0.035*
H8C	1.0691	0.8154	0.3916	0.035*
C9	0.5876 (7)	0.8032 (2)	0.3437 (2)	0.0248 (9)
H9A	0.4733	0.8102	0.3754	0.037*
H9B	0.5891	0.7492	0.3224	0.037*
H9C	0.5815	0.8410	0.2990	0.037*
C10	0.7885 (6)	0.8171 (2)	0.6203 (2)	0.0226 (8)
C11	0.7752 (6)	0.6928 (2)	0.4885 (2)	0.0186 (8)
H11	0.7724	0.6756	0.5427	0.022*
C12	0.7811 (6)	0.6338 (2)	0.4301 (2)	0.0194 (8)
H12	0.7896	0.6492	0.3756	0.023*
C13	0.7752 (6)	0.5539 (2)	0.4481 (2)	0.0189 (8)
H13	0.7644	0.5377	0.5022	0.023*
C14	0.7848 (6)	0.4965 (2)	0.3880 (2)	0.0174 (7)
H14	0.8006	0.5143	0.3347	0.021*
C15	0.7243 (6)	0.3835 (2)	0.4769 (2)	0.0187 (8)
H15A	0.5982	0.4037	0.4940	0.022*
H15B	0.8268	0.3944	0.5198	0.022*
C16	0.7121 (6)	0.2948 (2)	0.4578 (2)	0.0179 (8)
H16A	0.8381	0.2682	0.4716	0.021*
H16B	0.6091	0.2690	0.4874	0.021*
C17	0.6631 (7)	0.2927 (2)	0.3685 (3)	0.0273 (10)
H17A	0.5222	0.3017	0.3562	0.033*
H17B	0.7003	0.2413	0.3454	0.033*
C18	0.7825 (7)	0.3595 (2)	0.3367 (2)	0.0243 (9)
H18A	0.9184	0.3426	0.3298	0.029*
H18B	0.7245	0.3793	0.2847	0.029*
C19	0.2652 (9)	0.5381 (3)	0.2501 (3)	0.0406 (12)
H19A	0.3774	0.5352	0.2157	0.049*
H19B	0.1442	0.5349	0.2149	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0591 (9)	0.0256 (6)	0.0371 (7)	0.0013 (5)	0.0050 (5)	0.0016 (5)
Cl2	0.1031 (14)	0.0237 (6)	0.0465 (8)	−0.0009 (7)	0.0047 (8)	0.0022 (5)
O1	0.0335 (16)	0.0064 (11)	0.0131 (12)	0.0004 (10)	0.0044 (10)	0.0004 (9)
N1	0.091 (4)	0.024 (2)	0.023 (2)	−0.006 (2)	0.009 (2)	−0.0102 (16)
N2	0.047 (2)	0.0151 (16)	0.030 (2)	−0.0001 (16)	0.0008 (16)	0.0014 (15)
N3	0.063 (3)	0.028 (2)	0.023 (2)	−0.005 (2)	−0.0010 (18)	0.0067 (16)
N4	0.0282 (18)	0.0089 (14)	0.0157 (15)	−0.0017 (12)	0.0042 (12)	0.0002 (11)
C1	0.041 (3)	0.0099 (17)	0.024 (2)	−0.0014 (16)	0.0028 (18)	−0.0020 (14)
C2	0.028 (2)	0.0070 (15)	0.0210 (19)	−0.0003 (14)	0.0015 (15)	−0.0024 (13)
C3	0.030 (2)	0.0104 (17)	0.025 (2)	−0.0013 (14)	0.0018 (16)	−0.0033 (14)
C4	0.0151 (18)	0.0083 (15)	0.0213 (18)	−0.0007 (12)	0.0004 (13)	−0.0016 (13)
C5	0.024 (2)	0.0063 (15)	0.0175 (17)	−0.0030 (13)	0.0010 (14)	−0.0038 (12)
C6	0.0200 (18)	0.0115 (16)	0.0129 (16)	0.0021 (13)	−0.0007 (12)	−0.0012 (12)
C7	0.0216 (19)	0.0112 (15)	0.0141 (16)	−0.0020 (13)	0.0009 (13)	0.0010 (13)
C8	0.033 (2)	0.0152 (17)	0.0230 (19)	−0.0004 (16)	0.0060 (16)	0.0006 (15)
C9	0.042 (3)	0.0128 (17)	0.0189 (19)	−0.0034 (16)	−0.0066 (16)	−0.0003 (14)
C10	0.031 (2)	0.0120 (17)	0.024 (2)	−0.0043 (15)	−0.0023 (16)	−0.0018 (14)
C11	0.023 (2)	0.0105 (16)	0.0226 (18)	−0.0010 (14)	0.0026 (14)	0.0036 (14)
C12	0.024 (2)	0.0100 (16)	0.0238 (19)	−0.0005 (14)	0.0004 (15)	−0.0002 (14)
C13	0.028 (2)	0.0072 (15)	0.0219 (19)	−0.0015 (13)	0.0034 (15)	−0.0007 (13)
C14	0.0207 (19)	0.0081 (16)	0.0233 (19)	0.0021 (13)	0.0020 (14)	0.0019 (13)
C15	0.026 (2)	0.0129 (17)	0.0173 (18)	−0.0016 (14)	0.0023 (14)	0.0008 (13)
C16	0.0220 (19)	0.0093 (16)	0.0221 (18)	0.0018 (13)	−0.0011 (14)	0.0022 (13)
C17	0.040 (3)	0.0142 (18)	0.027 (2)	−0.0056 (17)	−0.0036 (18)	−0.0025 (15)
C18	0.045 (3)	0.0084 (16)	0.0198 (19)	0.0029 (16)	0.0033 (16)	−0.0041 (14)
C19	0.064 (4)	0.036 (3)	0.022 (2)	−0.001 (2)	0.003 (2)	0.0043 (18)

Geometric parameters (Å, º) top

Cl1—C19	1.766 (5)	C9—H9A	0.9800
Cl2—C19	1.753 (5)	C9—H9B	0.9800
O1—C6	1.341 (4)	C9—H9C	0.9800
O1—C5	1.482 (4)	C11—C12	1.397 (5)
N1—C1	1.160 (6)	C11—H11	0.9500
N2—C3	1.141 (5)	C12—C13	1.384 (5)
N3—C10	1.142 (5)	C12—H12	0.9500
N4—C14	1.317 (4)	C13—C14	1.397 (5)
N4—C18	1.471 (5)	C13—H13	0.9500
N4—C15	1.477 (5)	C14—H14	0.9500
C1—C2	1.408 (5)	C15—C16	1.533 (5)
C2—C6	1.388 (5)	C15—H15A	0.9900
C2—C3	1.423 (5)	C15—H15B	0.9900
C4—C7	1.402 (5)	C16—C17	1.505 (5)
C4—C11	1.405 (5)	C16—H16A	0.9900
C4—C5	1.503 (5)	C16—H16B	0.9900
C5—C9	1.510 (5)	C17—C18	1.510 (6)
C5—C8	1.514 (6)	C17—H17A	0.9900
C6—C7	1.412 (5)	C17—H17B	0.9900
C7—C10	1.421 (5)	C18—H18A	0.9900
C8—H8A	0.9800	C18—H18B	0.9900
C8—H8B	0.9800	C19—H19A	0.9900
C8—H8C	0.9800	C19—H19B	0.9900

C6—O1—C5	110.0 (3)	C13—C12—C11	122.9 (4)
C14—N4—C18	124.5 (3)	C13—C12—H12	118.6
C14—N4—C15	124.0 (3)	C11—C12—H12	118.6
C18—N4—C15	111.0 (3)	C12—C13—C14	121.2 (4)
N1—C1—C2	179.6 (5)	C12—C13—H13	119.4
C6—C2—C1	121.8 (3)	C14—C13—H13	119.4
C6—C2—C3	119.5 (3)	N4—C14—C13	124.7 (4)
C1—C2—C3	118.7 (3)	N4—C14—H14	117.7
N2—C3—C2	178.8 (5)	C13—C14—H14	117.7
C7—C4—C11	125.2 (3)	N4—C15—C16	103.7 (3)
C7—C4—C5	107.6 (3)	N4—C15—H15A	111.0
C11—C4—C5	127.2 (3)	C16—C15—H15A	111.0
O1—C5—C4	103.0 (3)	N4—C15—H15B	111.0
O1—C5—C9	105.2 (3)	C16—C15—H15B	111.0
C4—C5—C9	113.6 (3)	H15A—C15—H15B	109.0
O1—C5—C8	106.0 (3)	C17—C16—C15	103.6 (3)
C4—C5—C8	113.8 (3)	C17—C16—H16A	111.0
C9—C5—C8	113.9 (3)	C15—C16—H16A	111.0
O1—C6—C2	117.7 (3)	C17—C16—H16B	111.0
O1—C6—C7	110.6 (3)	C15—C16—H16B	111.0
C2—C6—C7	131.7 (3)	H16A—C16—H16B	109.0
C4—C7—C6	108.7 (3)	C16—C17—C18	103.7 (3)
C4—C7—C10	125.4 (3)	C16—C17—H17A	111.0
C6—C7—C10	125.8 (3)	C18—C17—H17A	111.0
C5—C8—H8A	109.5	C16—C17—H17B	111.0
C5—C8—H8B	109.5	C18—C17—H17B	111.0
H8A—C8—H8B	109.5	H17A—C17—H17B	109.0
C5—C8—H8C	109.5	N4—C18—C17	102.5 (3)
H8A—C8—H8C	109.5	N4—C18—H18A	111.3
H8B—C8—H8C	109.5	C17—C18—H18A	111.3
C5—C9—H9A	109.5	N4—C18—H18B	111.3
C5—C9—H9B	109.5	C17—C18—H18B	111.3
H9A—C9—H9B	109.5	H18A—C18—H18B	109.2
C5—C9—H9C	109.5	Cl2—C19—Cl1	111.0 (3)
H9A—C9—H9C	109.5	Cl2—C19—H19A	109.4
H9B—C9—H9C	109.5	Cl1—C19—H19A	109.4
N3—C10—C7	177.6 (4)	Cl2—C19—H19B	109.4
C12—C11—C4	126.9 (4)	Cl1—C19—H19B	109.4
C12—C11—H11	116.6	H19A—C19—H19B	108.0
C4—C11—H11	116.6

C6—O1—C5—C4	1.4 (4)	O1—C6—C7—C4	−1.5 (4)
C6—O1—C5—C9	120.7 (3)	C2—C6—C7—C4	177.8 (4)
C6—O1—C5—C8	−118.4 (3)	O1—C6—C7—C10	176.5 (4)
C7—C4—C5—O1	−2.3 (4)	C2—C6—C7—C10	−4.2 (7)
C11—C4—C5—O1	178.0 (4)	C7—C4—C11—C12	−177.7 (4)
C7—C4—C5—C9	−115.5 (3)	C5—C4—C11—C12	2.0 (6)
C11—C4—C5—C9	64.8 (5)	C4—C11—C12—C13	−177.4 (4)
C7—C4—C5—C8	112.0 (3)	C11—C12—C13—C14	−178.9 (4)
C11—C4—C5—C8	−67.8 (5)	C18—N4—C14—C13	179.6 (4)
C5—O1—C6—C2	−179.4 (3)	C15—N4—C14—C13	8.1 (6)
C5—O1—C6—C7	0.0 (4)	C12—C13—C14—N4	−177.6 (4)
C1—C2—C6—O1	178.0 (4)	C14—N4—C15—C16	175.1 (4)
C3—C2—C6—O1	−1.1 (6)	C18—N4—C15—C16	2.5 (4)
C1—C2—C6—C7	−1.2 (7)	N4—C15—C16—C17	−25.4 (4)
C3—C2—C6—C7	179.7 (4)	C15—C16—C17—C18	38.8 (4)
C11—C4—C7—C6	−177.9 (4)	C14—N4—C18—C17	−151.3 (4)
C5—C4—C7—C6	2.3 (4)	C15—N4—C18—C17	21.1 (4)
C11—C4—C7—C10	4.1 (6)	C16—C17—C18—N4	−36.7 (4)
C5—C4—C7—C10	−175.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N1ⁱ	0.95	2.52	3.378 (5)	150
C18—H18B···N1ⁱ	0.99	2.56	3.400 (5)	142

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₄O·CH₂Cl₂
M_r	391.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	6.8755 (8), 16.8913 (17), 16.6677 (18)
β (°)	93.482 (8)
V (Å³)	1932.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.30 × 0.15 × 0.13

Data collection
Diffractometer	Bruker–Nonius APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.570, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	4280, 4280, 2517
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.095, 0.270, 0.99
No. of reflections	4280
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.36, −0.47

Computer programs: APEX2 (Bruker, 2005), RLATT (Bruker, 2004), SAINT (Bruker, 2005) and SADABS (Sheldrick, 2003), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N1ⁱ	0.95	2.52	3.378 (5)	150
C18—H18B···N1ⁱ	0.99	2.56	3.400 (5)	142

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

We thank Dr J. Wikaira of the University of Canterbury, New Zealand, for her assistance in the data collection.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Bruker (2004). RLATT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2007). Acta Cryst. C63, o633–o637. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008a). Acta Cryst. C64, o195-o198. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gainsford, G. J., Bhuiyan, M. D. H., Kay, A. J. & Spek, A. L. (2008b). Acta Cryst. E64, o503. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008c). In preparation. Google Scholar
Kay, A. J., Woolhouse, A. D., Zhao, Y. & Clays, K. (2004). J. Mater. Chem. 14, 1321–1330. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-{3-Cyano-5,5-di­methyl-4-[4-(pyrrol­idin-1-yl)buta-1,3-dien­yl]-2,5-di­hydro­furan-2-yl­­idene}malono­nitrile di­chloro­methane solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-{3-Cyano-5,5-dimethyl-4-[4-(pyrrolidin-1-yl)buta-1,3-dienyl]-2,5-dihydrofuran-2-ylidene}malononitrile dichloromethane solvate