2-{4-[(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-yl­idene)methyl­amino]phen­yl}acetonitrile

Li, R.; Ding, Z.-Y.; Wei, Y.-Q.; Ding, J.

doi:10.1107/S1600536809017437

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1296

doi:10.1107/S1600536809017437

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2-{4-[(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methylamino]phenyl}acetonitrile

Rui Li,^a ^* Zhen-Yu Ding,^a Yu-Quan Wei ^a and Jian Ding ^b

^aState Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041, People's Republic of China, and ^bState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, People's Republic of China
^*Correspondence e-mail: lirui@scu.edu.cn

(Received 3 May 2009; accepted 8 May 2009; online 14 May 2009)

The title compound, C₁₅H₁₄N₂O₄, is approximately planar, with a dihedral angle of 6.48 (4)° between the aminomethylene unit and the planar five-atom part of the dioxane ring, and a dihedral angle of 2.40 (4)° between aminomethylene unit and the phenylene ring. The dioxane ring is envelope shaped, with the dimethyl-substituted C atom that represents the flap 0.535 (8) Å out of the plane. The molecule has an intramolecular N—H⋯O hydrogen bond.

Related literature

For the synthesis of related compounds, see: Cassis et al. (1985 ). For the synthesis of related antitumor precursors, see: Ruchelman et al. (2003 ). For the crystal structure of a related compound, see: da Silva et al. (2006 ). For Meldrum's acid, see: Meldrum (1908 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M_r = 286.28
Triclinic, $[P \overline 1]$
a = 5.204 (3) Å
b = 11.239 (3) Å
c = 12.209 (4) Å
α = 85.51 (3)°
β = 82.30 (3)°
γ = 84.54 (2)°
V = 702.9 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 292 K
0.52 × 0.48 × 0.23 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3217 measured reflections
2609 independent reflections
1610 reflections with I > 2σ(I)
R_int = 0.003
3 standard reflections every 150 reflections intensity decay: 1.3%

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.150
S = 1.09
2609 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O3	0.97 (2)	1.94 (2)	2.710 (3)	135 (2)

Data collection: DIFRAC (Gabe & White, 1993 ); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809017437/ng2579sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017437/ng2579Isup2.hkl

checkCIF report

Comment top

The 4(1H)quinolone structure plays an extremely important role in the field of pharmaceutical chemistry. These compounds have been used as precursors for anticancer agents, anti-malarial agents and reversible (H+/K+) ATPase inhibitors (Ruchelman et al.,2003). 5-arylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-diones are the key intermediates which can be used to synthesize the 4(1H)quinolone derivatives by thermolysis (Cassis et al., 1985).

In the structure of the title molecule (Fig. 1), it is approximately planar with the dihedral angles of 6.48 (4)° and 2.40 (4)° between the connecting aminomethylene unit and the planar part of the dioxane ring, and between the dimethoxybenzyl ring and the aminomethylene group, respectively. Besides, the dioxane ring of the title compound exhibits a half-boat conformation, in which the C atom between the dioxane oxygen atoms is -0.535 (8) Å out-of-plane.

The intramolecular N—H···O hydrogen bond (Table 1) is stabilizing the planar conformation in the molecule. Intermolecular weak C—H···O hydrogen bonding contacts (Table 1) result in the formation of sheets running parallel to the a-c plane in the crystal structure (Fig. 2).

Related literature top

For the synthesis of related compounds, see: Cassis et al. (1985). For the synthesis of related antitumor precursors, see: Ruchelman et al. (2003). For the crystal structure of a related compound, see: da Silva et al. (2006). For Meldrum's acid, see: Meldrum (1908).

Experimental top

A ethanol solution (50 ml) of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid) (1.44 g, 0.01 mol) and methylorthoformate (1.27 g, 0.012 mol) was heated to reflux for 2 h, then the arylamine (1.32 g, 0.01 mol) was added into the above solution. The mixture was heated under reflux for another 8 h and then filtered. Single crystals were obtained from the filtrate after 2 days.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound showing the layer-like aggregation of the title molecules in the unit cell.

2-{4-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methylamino]phenyl}acetonitrile top

Crystal data top

C₁₅H₁₄N₂O₄	Z = 2
M_r = 286.28	F(000) = 300
Triclinic, P1	D_x = 1.353 Mg m⁻³
a = 5.204 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.239 (3) Å	Cell parameters from 26 reflections
c = 12.209 (4) Å	θ = 5.5–9.7°
α = 85.51 (3)°	µ = 0.10 mm⁻¹
β = 82.30 (3)°	T = 292 K
γ = 84.54 (2)°	Block, colourless
V = 702.9 (5) Å³	0.52 × 0.48 × 0.23 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.003
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 1.7°
Graphite monochromator	h = −6→6
ω/2–θ scans	k = −2→13
3217 measured reflections	l = −14→14
2609 independent reflections	3 standard reflections every 150 reflections
1610 reflections with I > 2σ(I)	intensity decay: 1.3%

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)] = 0.048	Hydrogen site location: mixed
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0853P)²] where P = (F_o² + 2F_c²)/3
2609 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₄	γ = 84.54 (2)°
M_r = 286.28	V = 702.9 (5) Å³
Triclinic, P1	Z = 2
a = 5.204 (3) Å	Mo Kα radiation
b = 11.239 (3) Å	µ = 0.10 mm⁻¹
c = 12.209 (4) Å	T = 292 K
α = 85.51 (3)°	0.52 × 0.48 × 0.23 mm
β = 82.30 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.003
3217 measured reflections	3 standard reflections every 150 reflections
2609 independent reflections	intensity decay: 1.3%
1610 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.19 e Å⁻³
2609 reflections	Δρ_min = −0.20 e Å⁻³
196 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.5677 (3)	0.03464 (12)	0.29695 (11)	0.0620 (4)
O2	0.8342 (3)	0.19500 (12)	0.26775 (11)	0.0573 (4)
O3	0.2465 (3)	0.02806 (12)	0.43304 (11)	0.0639 (4)
O4	0.7647 (3)	0.35124 (12)	0.36881 (12)	0.0634 (4)
N1	0.1001 (3)	0.22676 (14)	0.54592 (13)	0.0498 (4)
H1N	0.074 (5)	0.145 (2)	0.5335 (18)	0.091 (8)*
N2	−0.9365 (5)	0.3352 (2)	0.9847 (2)	0.1123 (9)
C1	0.9231 (5)	0.0301 (2)	0.1573 (2)	0.0831 (8)
H1A	1.0196	0.0754	0.0984	0.125*
H1B	0.8480	−0.0329	0.1271	0.125*
H1C	1.0377	−0.0040	0.2090	0.125*
C2	0.5317 (5)	0.1765 (2)	0.13934 (18)	0.0744 (7)
H2A	0.3912	0.2203	0.1823	0.112*
H2B	0.4629	0.1198	0.0986	0.112*
H2C	0.6268	0.2311	0.0886	0.112*
C3	0.7107 (4)	0.11099 (19)	0.21537 (16)	0.0573 (6)
C4	0.4120 (4)	0.08606 (17)	0.38115 (16)	0.0519 (5)
C5	0.4624 (4)	0.20480 (16)	0.40360 (15)	0.0471 (5)
C6	0.6901 (4)	0.25836 (17)	0.34787 (15)	0.0477 (5)
C7	0.3046 (4)	0.26618 (16)	0.48329 (15)	0.0493 (5)
H7	0.3459	0.3428	0.4941	0.059*
C8	−0.0785 (4)	0.29056 (16)	0.62235 (15)	0.0472 (5)
C9	−0.2817 (4)	0.23184 (17)	0.67757 (17)	0.0568 (6)
H9	−0.2971	0.1528	0.6638	0.068*
C10	−0.4632 (4)	0.28879 (18)	0.75328 (16)	0.0573 (6)
H10	−0.5997	0.2476	0.7901	0.069*
C11	−0.4454 (4)	0.40591 (18)	0.77514 (16)	0.0507 (5)
C12	−0.2402 (4)	0.46434 (17)	0.71855 (16)	0.0535 (5)
H12	−0.2253	0.5435	0.7321	0.064*
C13	−0.0575 (4)	0.40860 (17)	0.64268 (16)	0.0541 (5)
H13	0.0786	0.4497	0.6055	0.065*
C14	−0.6446 (4)	0.47201 (19)	0.85500 (16)	0.0608 (6)
H14A	−0.5548	0.5184	0.8994	0.073*
H14B	−0.7541	0.5278	0.8130	0.073*
C15	−0.8082 (5)	0.3952 (2)	0.92822 (19)	0.0722 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0652 (9)	0.0508 (8)	0.0660 (9)	−0.0175 (7)	0.0196 (7)	−0.0113 (7)
O2	0.0452 (8)	0.0627 (8)	0.0639 (9)	−0.0173 (7)	0.0036 (7)	−0.0054 (7)
O3	0.0655 (9)	0.0509 (8)	0.0712 (9)	−0.0237 (7)	0.0208 (7)	−0.0066 (7)
O4	0.0655 (10)	0.0527 (8)	0.0744 (9)	−0.0237 (7)	−0.0061 (8)	−0.0008 (7)
N1	0.0521 (10)	0.0400 (9)	0.0560 (9)	−0.0069 (8)	0.0003 (8)	−0.0045 (7)
N2	0.112 (2)	0.0951 (17)	0.1082 (18)	−0.0057 (15)	0.0499 (16)	0.0130 (14)
C1	0.0696 (17)	0.0865 (18)	0.0876 (17)	−0.0170 (15)	0.0277 (14)	−0.0232 (15)
C2	0.0662 (15)	0.0952 (18)	0.0641 (14)	−0.0285 (14)	−0.0041 (12)	−0.0003 (13)
C3	0.0520 (12)	0.0619 (12)	0.0571 (12)	−0.0221 (11)	0.0108 (10)	−0.0073 (10)
C4	0.0511 (12)	0.0481 (11)	0.0539 (11)	−0.0108 (10)	0.0060 (10)	−0.0019 (9)
C5	0.0457 (11)	0.0442 (10)	0.0507 (11)	−0.0097 (9)	−0.0017 (9)	0.0007 (9)
C6	0.0449 (11)	0.0456 (10)	0.0523 (11)	−0.0087 (9)	−0.0041 (9)	0.0016 (9)
C7	0.0522 (12)	0.0413 (10)	0.0537 (11)	−0.0080 (9)	−0.0031 (10)	0.0001 (9)
C8	0.0477 (11)	0.0442 (10)	0.0489 (11)	−0.0069 (9)	−0.0019 (9)	−0.0016 (8)
C9	0.0632 (14)	0.0410 (11)	0.0657 (13)	−0.0151 (10)	0.0017 (11)	−0.0055 (10)
C10	0.0567 (13)	0.0499 (11)	0.0631 (13)	−0.0166 (10)	0.0086 (10)	−0.0036 (10)
C11	0.0506 (12)	0.0497 (11)	0.0501 (11)	−0.0044 (9)	−0.0022 (9)	0.0003 (9)
C12	0.0563 (13)	0.0397 (10)	0.0630 (12)	−0.0061 (9)	0.0018 (10)	−0.0068 (9)
C13	0.0505 (12)	0.0472 (11)	0.0628 (12)	−0.0106 (10)	0.0037 (10)	−0.0029 (9)
C14	0.0619 (14)	0.0592 (12)	0.0572 (12)	−0.0039 (11)	0.0071 (11)	−0.0049 (10)
C15	0.0707 (16)	0.0721 (15)	0.0639 (14)	0.0053 (13)	0.0158 (12)	0.0019 (12)

Geometric parameters (Å, º) top

O1—C4	1.352 (2)	C4—C5	1.438 (2)
O1—C3	1.439 (2)	C5—C7	1.371 (3)
O2—C6	1.356 (2)	C5—C6	1.444 (3)
O2—C3	1.426 (2)	C7—H7	0.9300
O3—C4	1.210 (2)	C8—C9	1.371 (3)
O4—C6	1.205 (2)	C8—C13	1.386 (3)
N1—C7	1.316 (2)	C9—C10	1.379 (3)
N1—C8	1.412 (2)	C9—H9	0.9300
N1—H1n	0.96 (2)	C10—C11	1.378 (3)
N2—C15	1.125 (3)	C10—H10	0.9300
C1—C3	1.500 (3)	C11—C12	1.383 (3)
C1—H1A	0.9600	C11—C14	1.508 (3)
C1—H1B	0.9600	C12—C13	1.377 (3)
C1—H1C	0.9600	C12—H12	0.9300
C2—C3	1.505 (3)	C13—H13	0.9300
C2—H2A	0.9600	C14—C15	1.444 (3)
C2—H2B	0.9600	C14—H14A	0.9700
C2—H2C	0.9600	C14—H14B	0.9700

C4—O1—C3	118.27 (15)	O4—C6—C5	125.76 (19)
C6—O2—C3	118.41 (15)	O2—C6—C5	115.95 (15)
C7—N1—C8	127.60 (16)	N1—C7—C5	126.03 (17)
C7—N1—H1N	112.8 (15)	N1—C7—H7	117.0
C8—N1—H1N	119.5 (15)	C5—C7—H7	117.0
C3—C1—H1A	109.5	C9—C8—C13	119.39 (18)
C3—C1—H1B	109.5	C9—C8—N1	117.65 (16)
H1A—C1—H1B	109.5	C13—C8—N1	122.96 (17)
C3—C1—H1C	109.5	C8—C9—C10	120.69 (17)
H1A—C1—H1C	109.5	C8—C9—H9	119.7
H1B—C1—H1C	109.5	C10—C9—H9	119.7
C3—C2—H2A	109.5	C11—C10—C9	120.89 (19)
C3—C2—H2B	109.5	C11—C10—H10	119.6
H2A—C2—H2B	109.5	C9—C10—H10	119.6
C3—C2—H2C	109.5	C10—C11—C12	117.88 (19)
H2A—C2—H2C	109.5	C10—C11—C14	122.30 (19)
H2B—C2—H2C	109.5	C12—C11—C14	119.80 (17)
O2—C3—O1	110.49 (15)	C13—C12—C11	121.86 (17)
O2—C3—C1	106.90 (17)	C13—C12—H12	119.1
O1—C3—C1	105.58 (18)	C11—C12—H12	119.1
O2—C3—C2	109.82 (18)	C12—C13—C8	119.30 (18)
O1—C3—C2	110.28 (17)	C12—C13—H13	120.4
C1—C3—C2	113.65 (19)	C8—C13—H13	120.4
O3—C4—O1	117.85 (16)	C15—C14—C11	114.09 (18)
O3—C4—C5	125.29 (18)	C15—C14—H14A	108.7
O1—C4—C5	116.83 (16)	C11—C14—H14A	108.7
C7—C5—C4	120.65 (17)	C15—C14—H14B	108.7
C7—C5—C6	118.69 (16)	C11—C14—H14B	108.7
C4—C5—C6	120.53 (17)	H14A—C14—H14B	107.6
O4—C6—O2	118.25 (17)	N2—C15—C14	179.5 (3)

C6—O2—C3—O1	−49.2 (2)	C8—N1—C7—C5	−174.51 (18)
C6—O2—C3—C1	−163.65 (17)	C4—C5—C7—N1	0.3 (3)
C6—O2—C3—C2	72.6 (2)	C6—C5—C7—N1	−175.62 (18)
C4—O1—C3—O2	46.8 (2)	C7—N1—C8—C9	178.79 (18)
C4—O1—C3—C1	162.08 (18)	C7—N1—C8—C13	−0.7 (3)
C4—O1—C3—C2	−74.8 (2)	C13—C8—C9—C10	−0.4 (3)
C3—O1—C4—O3	162.19 (19)	N1—C8—C9—C10	−179.96 (18)
C3—O1—C4—C5	−19.5 (3)	C8—C9—C10—C11	0.1 (3)
O3—C4—C5—C7	−5.6 (3)	C9—C10—C11—C12	0.2 (3)
O1—C4—C5—C7	176.25 (17)	C9—C10—C11—C14	178.25 (19)
O3—C4—C5—C6	170.2 (2)	C10—C11—C12—C13	−0.1 (3)
O1—C4—C5—C6	−7.9 (3)	C14—C11—C12—C13	−178.27 (19)
C3—O2—C6—O4	−158.33 (18)	C11—C12—C13—C8	−0.2 (3)
C3—O2—C6—C5	23.8 (2)	C9—C8—C13—C12	0.4 (3)
C7—C5—C6—O4	4.2 (3)	N1—C8—C13—C12	179.96 (18)
C4—C5—C6—O4	−171.73 (19)	C10—C11—C14—C15	16.7 (3)
C7—C5—C6—O2	−178.17 (16)	C12—C11—C14—C15	−165.3 (2)
C4—C5—C6—O2	5.9 (3)	C11—C14—C15—N2	−69 (31)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O3	0.97 (2)	1.94 (2)	2.710 (3)	135 (2)
C7—H7···O4	0.93	2.49	2.816 (3)	100
C9—H9···O3ⁱ	0.93	2.41	3.292 (3)	159
C13—H13···O4ⁱⁱ	0.93	2.51	3.208 (3)	132
C14—H14B···O4ⁱⁱⁱ	0.97	2.51	3.343 (3)	143

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₄
M_r	286.28
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	5.204 (3), 11.239 (3), 12.209 (4)
α, β, γ (°)	85.51 (3), 82.30 (3), 84.54 (2)
V (Å³)	702.9 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.52 × 0.48 × 0.23

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3217, 2609, 1610
R_int	0.003
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.150, 1.09
No. of reflections	2609
No. of parameters	196
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O3	0.97 (2)	1.94 (2)	2.710 (3)	135 (2)

Acknowledgements

This research was supported financially by the State Key Laboratory of Drug Research (Shanghai Institute of Materia Medica, Chinese Academy of Sciences).

References

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Volume 65| Part 6| June 2009| Page o1296

doi:10.1107/S1600536809017437

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

2-{4-[(2,2-Di­methyl-4,6-dioxo-1,3-dioxan-5-yl­­idene)methyl­amino]phen­yl}aceto­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-{4-[(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methylamino]phenyl}acetonitrile