2-{4-[(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-yl-idene)methyl-amino]phen-yl}acetonitrile.

The title compound, C(15)H(14)N(2)O(4), is approximately planar, with a dihedral angle of 6.48 (4)° between the amino-methyl-ene unit and the planar five-atom part of the dioxane ring, and a dihedral angle of 2.40 (4)° between amino-methyl-ene unit and the phenyl-ene 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 mol-ecule has an intra-molecular 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 = 286.28

Triclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.150

S = 1.09

2609 reflections

196 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

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 ▶).

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

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

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

C15H14N2O4	Z = 2
Mr = 286.28	F(000) = 300
Triclinic, P1	Dx = 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

Enraf–Nonius CAD-4 diffractometer	Rint = 0.003
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 1.7°
graphite	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 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(Fo2) + (0.0853P)2] where P = (Fo2 + 2Fc2)/3
2609 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.20 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
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)

	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)

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)

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

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)