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

Blessing

Farrugia

Gainsford

Sheldrick

Spek

English

PubMed

Crossref

2-{3-Cyano-5,5-dimethyl-4-[4-(pyrrol-
idin-1-yl)buta-1,3-dienyl]-2,5-dihydro-
furan-2-ylidene}malononitrile
dichloromethane solvate
Graeme J. Gainsford,a* M. Delower H. Bhuiyan,a
Andrew J. Kaya and Ward T. Robinsonb
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
Key indicators: single-crystal X-ray study; T = 120 K; mean (C–C) = 0.005 A˚;
R factor = 0.096; wR factor = 0.270; data-to-parameter ratio = 18.1.
The structure of the title compound, C18H18N4OCH2Cl2, 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
C18H18N4OCH2Cl2
Mr = 391.29
Monoclinic, P21=c
a = 6.8755 (8) A˚
b = 16.8913 (17) A˚
c = 16.6677 (18) A˚
 = 93.482 (8)
V = 1932.1 (4) A˚3
Z = 4
Mo K radiation
 = 0.35 mm1
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)
Tmin = 0.570, Tmax = 0.955
4280 measured reflections
4280 independent reflections
2517 reflections with I > 2(I)
Rint = 0.099
Refinement
R[F 2 > 2(F 2)] = 0.095
wR(F 2) = 0.270
S = 0.99
4280 reflections
237 parameters
H-atom parameters constrained
max = 1.36 e A˚
3
min = 0.47 e A˚3
Table 1
Hydrogen-bond geometry (A˚, ).
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;yþ 32; z 12.
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.
We thank Dr J. Wikaira of the University of Canterbury,
New Zealand, for her assistance in the data collection.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: LH2664).
References
Blessing, R. H. (1995). Acta Cryst. A51, 33–38.
Bruker (2004). RLATT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,
Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2007). Acta Cryst. C63, o633–
o637.
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008a). Acta Cryst. C64,
o195-o198.
Gainsford, G. J., Bhuiyan, M. D. H., Kay, A. J. & Spek, A. L. (2008b). Acta
Cryst. E64, o503.
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008c). In preparation.
Kay, A. J., Woolhouse, A. D., Zhao, Y. & Clays, K. (2004). J. Mater. Chem. 14,
1321–1330.
Sheldrick, G. M. (2003). SADABS. University of Go¨ttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.
organic compounds
Acta Cryst. (2008). E64, o1715 doi:10.1107/S1600536808024719 Gainsford et al. o1715
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
supporting information
sup-1Acta Cryst. (2008). E64, o1715    
supporting information
Acta Cryst. (2008). E64, o1715    [doi:10.1107/S1600536808024719]
2-{3-Cyano-5,5-dimethyl-4-[4-(pyrrolidin-1-yl)buta-1,3-dienyl]-2,5-dihydro-
furan-2-ylidene}malononitrile dichloromethane solvate
Graeme J. Gainsford, M. Delower H. Bhuiyan, Andrew J. Kay and Ward T. Robinson
S1. Comment 
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.
S2. Experimental 
To a solution of 5.8 mmole of {4-(4-Acetanilido-trans-1,3-butadienyl) -3-cyano-5,5-dimethyl-2(5H)-furan-
ylidene}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. λmax 
530 nm (pyridine); 530 nm (DMF) log10ε 5.22. Final crystallization was from a 1:1 dichloromethane/ ethyl acetate 
mixture.
S3. Refinement 
Diffraction data was extracted from the major of multiple intersecting lattices using RLATT (Bruker, 2004). The structure 
was solved by direct methods but refinement halted at R 0.20 for 3731 data with I>2σ(I). Inspection of data showed a 
large number with Fo>>Fc indicating coincidental contributions from the other contributing lattice(s). A total of 943 
reflections which met the two criteria (1) I(obs)/I(calc) > 1.50 and (2) (I(obs)-I(calc)) > 2σ(I(obs)) were then excluded 
from the dataset. The conventional R for these rejected data was 0.47. The ratio criteria (1) was varied down to values of 
1.05: although the agreement factors converged at around a ratio of 1.2 (R 0.078, for 2252 I>2σ(I) data) no signifcant 
changes occurred in final su values or parameters compared with the larger dataset. On the basis that another analysis of 
the data would be possible if the larger dataset was presented, the refinement was continued with the (ratio 1.5) 4280 
independent remaining data within the limit of 29° theta. All methyl and tertiary H atoms were refined with Uiso 1.5 & 1.2 
times respectively that of the Ueq of their parent atom.
supporting information
sup-2Acta Cryst. (2008). E64, o1715    
Figure 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 
Crystal data 
C18H18N4O·CH2Cl2
Mr = 391.29
Monoclinic, P21/c
Hall symbol: -P 2ybc
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
F(000) = 816
Dx = 1.345 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 5595 reflections
θ = 2.4–29.2°
µ = 0.35 mm−1
T = 120 K
Block, red
0.30 × 0.15 × 0.13 mm
Data collection 
Bruker–Nonius APEXII CCD area-detector 
diffractometer
Radiation source: fine-focus sealed tube
Graphite monochromator
Detector resolution: 8.192 pixels mm-1
φ and ω scans
Absorption correction: multi-scan 
(Blessing, 1995)
Tmin = 0.570, Tmax = 0.955
4280 measured reflections
4280 independent reflections
2517 reflections with I > 2σ(I)
Rint = 0.099
θmax = 29.0°, θmin = 2.7°
h = −9→9
k = 0→23
l = 0→22
Refinement 
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.095
wR(F2) = 0.270
S = 0.99
4280 reflections
237 parameters
0 restraints
Primary atom site location: structure-invariant 
direct methods
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sup-3Acta Cryst. (2008). E64, o1715    
Secondary atom site location: difference Fourier 
map
Hydrogen site location: inferred from 
neighbouring sites
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.1824P)2] 
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 1.36 e Å−3
Δρmin = −0.47 e Å−3
Special details 
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) 
x y z Uiso*/Ueq
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)
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sup-4Acta Cryst. (2008). E64, o1715    
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) 
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)
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sup-5Acta Cryst. (2008). E64, o1715    
Geometric parameters (Å, º) 
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)
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sup-6Acta Cryst. (2008). E64, o1715    
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) 
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.


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

The structure of the title compound, C18H18N4O&#183;CH2Cl2, was solved using data collected from a multiple crystal (note high R factors). The crystal structure is dominated by two bifurcated attractive C&#8212;H...N(cyano) interactions

Ward T. Robinson

Andrew J. Kay

M. Delower H. Bhuiyan

Graeme J. Gainsford

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Acta Crystallographica Section E Structure Reports Online

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/Ueq Cl1

organic compounds Acta Cryst.

http://doaj.org/search?source=%7B%22query%22%3A%7B%22bool%22%3A%7B%22must%22%3A%5B%7B%22term%22%3A%7B%22id%22%3A%22a1629ecfba1349c0bdf8c5ef32712657%22%7D%7D%5D%7D%7D%7D

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

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

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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

Abstract

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Full text

Available Versions

Crossref

Directory of Open Access Journals

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