2-{3-Cyano-5,5-dimethyl-4-[4-(pyrrol-idin-1-yl)buta-1,3-dien-yl]-2,5-dihydro-furan-2-yl-idene}malononitrile dichloro-methane solvate.

The structure of the title compound, C(18)H(18)N(4)O·CH(2)Cl(2), 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) inter-actions.

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 = 391.29

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.095

wR(F 2) = 0.270

S = 0.99

4280 reflections

237 parameters

H-atom parameters constrained

Δρmax = 1.36 e Å−3

Δρmin = −0.47 e Å−3

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.

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

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

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

C18H18N4O·CH2Cl2	F000 = 816
Mr = 391.29	Dx = 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 = 2.4–29.2º
b = 16.8913 (17) Å	µ = 0.35 mm−1
c = 16.6677 (18) Å	T = 120 (2) K
β = 93.482 (8)º	Block, red
V = 1932.1 (4) Å3	0.30 × 0.15 × 0.13 mm
Z = 4

Bruker–Nonius APEXII CCD area-detector diffractometer	4280 independent reflections
Radiation source: fine-focus sealed tube	2517 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.099
Detector resolution: 8.192 pixels mm-1	θmax = 29.0º
T = 120(2) K	θmin = 2.7º
φ and ω scans	h = −9→9
Absorption correction: multi-scan(Blessing, 1995)	k = 0→23
Tmin = 0.570, Tmax = 0.955	l = 0→22
4280 measured reflections

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)] = 0.095	H-atom parameters constrained
wR(F2) = 0.270	w = 1/[σ2(Fo2) + (0.1824P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
4280 reflections	Δρmax = 1.36 e Å−3
237 parameters	Δρmin = −0.47 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	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)
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*

	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)

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)

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

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) .