5-[(4-Acetyl-phenyl)-aminomethyl-ene]-2,2-dimethyl-1,3-dioxane-4,6-dione.

In the title compound, C(15)H(15)NO(5), the six-membered dioxane ring assumes an envelope conformation with the dimethyl substituted C atom as the flap atom. An intra-molecular N-H⋯O inter-action is also present. In the crystal structure the mol-ecules are linked via C-H⋯O hydrogen bonds into supra-molecular chains along the b axis.

Related literature

For the biological activity of 4(1H)-quinolone structures, see: Ruchelman et al. (2003 ▶). 5-Aryl­amino­methyl­ene-2,2-dimethyl-1,3-dioxane-4,6-diones are key inter­mediates in the synthesis of 4(1H)quinolone derivatives by thermolysis (Cassis et al., 1985 ▶).

Experimental

Crystal data

C15H15NO5

M = 289.28

Triclinic,

a = 7.102 (3) Å

b = 7.356 (4) Å

c = 13.856 (4) Å

α = 82.79 (4)°

β = 83.19 (4)°

γ = 86.03 (4)°

V = 712.0 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 292 K

0.44 × 0.36 × 0.32 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2894 measured reflections

2621 independent reflections

1399 reflections with I > 2σ(I)

R int = 0.008

3 standard reflections every 100 reflections intensity decay: 1.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.179

S = 1.03

2621 reflections

197 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.34 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.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809017425/xu2521sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017425/xu2521Isup2.hkl

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

C15H15NO5	Z = 2
Mr = 289.28	F(000) = 304
Triclinic, P1	Dx = 1.349 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.102 (3) Å	Cell parameters from 25 reflections
b = 7.356 (4) Å	θ = 4.4–7.4°
c = 13.856 (4) Å	µ = 0.10 mm−1
α = 82.79 (4)°	T = 292 K
β = 83.19 (4)°	Block, colourless
γ = 86.03 (4)°	0.44 × 0.36 × 0.32 mm
V = 712.0 (5) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.008
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 1.5°
graphite	h = −8→8
ω/2θ scans	k = −3→8
2894 measured reflections	l = −16→16
2621 independent reflections	3 standard reflections every 100 reflections
1399 reflections with I > 2σ(I)	intensity decay: 1.8%

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0987P)2] where P = (Fo2 + 2Fc2)/3
2621 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.34 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	0.4606 (3)	0.5224 (2)	0.87501 (13)	0.0548 (6)
O2	0.4847 (3)	0.3153 (3)	0.75537 (13)	0.0585 (6)
O3	0.5363 (3)	0.8104 (3)	0.83800 (15)	0.0713 (7)
O4	0.5696 (3)	0.4044 (3)	0.60005 (14)	0.0688 (7)
O5	0.9300 (3)	1.4570 (3)	0.25900 (17)	0.0767 (7)
N1	0.6950 (3)	0.7445 (3)	0.54722 (17)	0.0485 (6)
H1N	0.674 (4)	0.644 (5)	0.528 (2)	0.066 (9)*
C1	0.3511 (5)	0.2250 (4)	0.9154 (2)	0.0677 (9)
H1A	0.3605	0.2286	0.9836	0.101*
H1B	0.3674	0.1003	0.9010	0.101*
H1C	0.2284	0.2754	0.8999	0.101*
C2	0.6988 (5)	0.2750 (5)	0.8795 (2)	0.0708 (9)
H2A	0.7894	0.3472	0.8371	0.106*
H2B	0.7236	0.1478	0.8706	0.106*
H2C	0.7094	0.2910	0.9463	0.106*
C3	0.5022 (4)	0.3356 (4)	0.8554 (2)	0.0504 (7)
C4	0.5331 (4)	0.6609 (4)	0.8097 (2)	0.0503 (7)
C5	0.5861 (4)	0.6195 (3)	0.71100 (18)	0.0440 (6)
C6	0.5512 (4)	0.4421 (4)	0.6835 (2)	0.0486 (7)
C7	0.6522 (4)	0.7568 (3)	0.64119 (19)	0.0443 (7)
H7	0.6681	0.8692	0.6625	0.053*
C8	0.7584 (4)	0.8835 (4)	0.47359 (19)	0.0443 (7)
C9	0.8222 (4)	0.8338 (4)	0.3821 (2)	0.0561 (8)
H9	0.8262	0.7113	0.3711	0.067*
C10	0.8804 (4)	0.9674 (4)	0.3063 (2)	0.0562 (8)
H10	0.9233	0.9337	0.2447	0.067*
C11	0.8752 (4)	1.1500 (4)	0.3217 (2)	0.0475 (7)
C12	0.8132 (4)	1.1971 (4)	0.4143 (2)	0.0510 (7)
H12	0.8113	1.3192	0.4256	0.061*
C13	0.7541 (4)	1.0661 (4)	0.4903 (2)	0.0491 (7)
H13	0.7118	1.0998	0.5521	0.059*
C14	0.9294 (4)	1.2990 (4)	0.2415 (2)	0.0558 (8)
C15	0.9783 (5)	1.2522 (5)	0.1391 (2)	0.0731 (10)
H15A	1.0042	1.3622	0.0958	0.110*
H15B	0.8735	1.1954	0.1195	0.110*
H15C	1.0885	1.1690	0.1365	0.110*

	U11	U22	U33	U12	U13	U23
O1	0.0800 (14)	0.0361 (11)	0.0476 (11)	0.0014 (9)	−0.0018 (10)	−0.0097 (9)
O2	0.0936 (15)	0.0361 (11)	0.0467 (11)	−0.0137 (10)	−0.0013 (10)	−0.0087 (9)
O3	0.125 (2)	0.0320 (11)	0.0598 (12)	−0.0023 (11)	−0.0121 (12)	−0.0163 (9)
O4	0.1213 (19)	0.0381 (11)	0.0475 (12)	−0.0173 (12)	0.0040 (11)	−0.0130 (9)
O5	0.0993 (18)	0.0370 (13)	0.0893 (17)	−0.0106 (11)	0.0019 (13)	0.0012 (11)
N1	0.0641 (16)	0.0299 (13)	0.0525 (15)	−0.0091 (11)	−0.0043 (12)	−0.0071 (11)
C1	0.087 (2)	0.056 (2)	0.0591 (19)	−0.0135 (17)	0.0026 (17)	−0.0095 (16)
C2	0.078 (2)	0.053 (2)	0.078 (2)	0.0051 (16)	−0.0068 (18)	0.0021 (16)
C3	0.071 (2)	0.0296 (14)	0.0505 (16)	0.0001 (13)	−0.0032 (14)	−0.0068 (12)
C4	0.0647 (19)	0.0389 (16)	0.0488 (16)	0.0057 (13)	−0.0135 (14)	−0.0092 (13)
C5	0.0512 (16)	0.0371 (15)	0.0455 (15)	0.0007 (12)	−0.0106 (13)	−0.0086 (12)
C6	0.0670 (19)	0.0346 (15)	0.0435 (16)	−0.0027 (13)	−0.0018 (13)	−0.0065 (12)
C7	0.0527 (16)	0.0300 (14)	0.0525 (17)	−0.0017 (12)	−0.0121 (13)	−0.0086 (12)
C8	0.0449 (16)	0.0374 (15)	0.0520 (16)	−0.0071 (12)	−0.0067 (12)	−0.0067 (12)
C9	0.069 (2)	0.0416 (16)	0.0597 (18)	−0.0133 (14)	0.0005 (15)	−0.0137 (14)
C10	0.0639 (19)	0.0526 (19)	0.0525 (17)	−0.0094 (15)	0.0036 (14)	−0.0140 (14)
C11	0.0434 (16)	0.0431 (16)	0.0548 (17)	−0.0042 (12)	−0.0029 (13)	−0.0029 (13)
C12	0.0608 (19)	0.0312 (14)	0.0611 (18)	−0.0040 (12)	−0.0069 (14)	−0.0048 (13)
C13	0.0588 (18)	0.0377 (15)	0.0518 (16)	0.0021 (13)	−0.0048 (13)	−0.0129 (13)
C14	0.0464 (17)	0.0531 (19)	0.066 (2)	0.0003 (14)	−0.0062 (14)	−0.0001 (15)
C15	0.083 (2)	0.063 (2)	0.065 (2)	−0.0021 (18)	0.0077 (18)	0.0072 (16)

O1—C4	1.361 (3)	C5—C7	1.374 (4)
O1—C3	1.438 (3)	C5—C6	1.450 (4)
O2—C6	1.342 (3)	C7—H7	0.9300
O2—C3	1.434 (3)	C8—C9	1.380 (4)
O3—C4	1.216 (3)	C8—C13	1.389 (4)
O4—C6	1.212 (3)	C9—C10	1.390 (4)
O5—C14	1.217 (3)	C9—H9	0.9300
N1—C7	1.315 (3)	C10—C11	1.383 (4)
N1—C8	1.408 (3)	C10—H10	0.9300
N1—H1N	0.85 (3)	C11—C12	1.384 (4)
C1—C3	1.498 (4)	C11—C14	1.495 (4)
C1—H1A	0.9600	C12—C13	1.383 (4)
C1—H1B	0.9600	C12—H12	0.9300
C1—H1C	0.9600	C13—H13	0.9300
C2—C3	1.499 (4)	C14—C15	1.497 (4)
C2—H2A	0.9600	C15—H15A	0.9600
C2—H2B	0.9600	C15—H15B	0.9600
C2—H2C	0.9600	C15—H15C	0.9600
C4—C5	1.438 (3)
C4—O1—C3	119.3 (2)	O2—C6—C5	117.1 (2)
C6—O2—C3	120.1 (2)	N1—C7—C5	126.2 (2)
C7—N1—C8	127.6 (2)	N1—C7—H7	116.9
C7—N1—H1N	116 (2)	C5—C7—H7	116.9
C8—N1—H1N	116 (2)	C9—C8—C13	120.2 (3)
C3—C1—H1A	109.5	C9—C8—N1	117.8 (3)
C3—C1—H1B	109.5	C13—C8—N1	122.0 (2)
H1A—C1—H1B	109.5	C8—C9—C10	119.7 (3)
C3—C1—H1C	109.5	C8—C9—H9	120.1
H1A—C1—H1C	109.5	C10—C9—H9	120.1
H1B—C1—H1C	109.5	C11—C10—C9	120.7 (3)
C3—C2—H2A	109.5	C11—C10—H10	119.7
C3—C2—H2B	109.5	C9—C10—H10	119.7
H2A—C2—H2B	109.5	C10—C11—C12	118.8 (3)
C3—C2—H2C	109.5	C10—C11—C14	122.5 (3)
H2A—C2—H2C	109.5	C12—C11—C14	118.7 (3)
H2B—C2—H2C	109.5	C13—C12—C11	121.3 (3)
O2—C3—O1	111.4 (2)	C13—C12—H12	119.4
O2—C3—C1	105.9 (2)	C11—C12—H12	119.4
O1—C3—C1	106.4 (2)	C12—C13—C8	119.3 (3)
O2—C3—C2	110.2 (2)	C12—C13—H13	120.4
O1—C3—C2	109.4 (2)	C8—C13—H13	120.4
C1—C3—C2	113.4 (3)	O5—C14—C11	120.4 (3)
O3—C4—O1	117.5 (2)	O5—C14—C15	120.4 (3)
O3—C4—C5	125.9 (3)	C11—C14—C15	119.2 (3)
O1—C4—C5	116.5 (2)	C14—C15—H15A	109.5
C7—C5—C4	118.8 (2)	C14—C15—H15B	109.5
C7—C5—C6	120.4 (2)	H15A—C15—H15B	109.5
C4—C5—C6	120.5 (2)	C14—C15—H15C	109.5
O4—C6—O2	118.4 (2)	H15A—C15—H15C	109.5
O4—C6—C5	124.5 (3)	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.84 (4)	2.05 (3)	2.699 (3)	133 (2)
C1—H1B···O3i	0.96	2.57	3.480 (4)	158
C9—H9···O5i	0.93	2.59	3.429 (4)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4	0.84 (4)	2.05 (3)	2.699 (3)	133 (2)
C1—H1B⋯O3i	0.96	2.57	3.480 (4)	158
C9—H9⋯O5i	0.93	2.59	3.429 (4)	150

Symmetry code: (i) .