2,2-Dimethyl-5-(1-naphthyl-amino-methyl-ene)-1,3-dioxane-4,6-dione.

The benzyl ring of the title compound, C(17)H(15)NO(4), is twisted away from the plane defined by five atoms of the dioxane ring by 34.83 (4)°. The dioxane ring exhibits a half-boat conformation, with the C atom between the dioxane O atoms 0.571 (8) Å out of the plane through the remainder of the ring. An intra-molecular N-H⋯O hydrogen bond may contribute to the stabilization of the planar conformation of the mol-ecule. In the crystal, inversion dimers linked by pairs of C-H⋯O bonds occur.

Related literature

For the synthesis of related compounds, see: Cassis et al. (1985 ▶). For the pharmacological activity of 4(1H)-quinolone structures, see: Ruchelman et al. (2003 ▶).

Experimental

Crystal data

C17H15NO4

M = 297.30

Triclinic,

a = 7.4696 (11) Å

b = 8.0805 (12) Å

c = 12.1240 (18) Å

α = 98.601 (2)°

β = 96.428 (2)°

γ = 92.198 (2)°

V = 717.87 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 153 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

4513 measured reflections

3194 independent reflections

2571 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.03

3194 reflections

206 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033984/ez2178sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033984/ez2178Isup2.hkl

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

C17H15NO4	Z = 2
Mr = 297.30	F(000) = 312
Triclinic, P1	Dx = 1.375 Mg m−3
a = 7.4696 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0805 (12) Å	Cell parameters from 2197 reflections
c = 12.1240 (18) Å	θ = 2.6–27.5°
α = 98.601 (2)°	µ = 0.10 mm−1
β = 96.428 (2)°	T = 153 K
γ = 92.198 (2)°	Block, colourless
V = 717.87 (18) Å3	0.25 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	2571 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
graphite	θmax = 27.6°, θmin = 2.6°
φ and ω scans	h = −9→6
4513 measured reflections	k = −10→10
3194 independent reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0462P)2 + 0.1278P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3194 reflections	Δρmax = 0.18 e Å−3
206 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.204 (9)

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	0.75507 (13)	0.44446 (12)	0.48110 (8)	0.0482 (3)
O2	0.61634 (12)	0.29559 (12)	0.60505 (7)	0.0468 (3)
O3	0.66547 (15)	0.40648 (13)	0.29855 (8)	0.0567 (3)
O4	0.36615 (13)	0.13711 (12)	0.54766 (8)	0.0501 (3)
N1	0.41749 (15)	0.15238 (15)	0.21325 (9)	0.0431 (3)
H1	0.496 (3)	0.236 (2)	0.2012 (15)	0.074 (5)*
C1	0.9036 (2)	0.21096 (19)	0.54644 (13)	0.0529 (4)
H1A	0.9247	0.1511	0.6109	0.079*
H1B	1.0193	0.2541	0.5281	0.079*
H1C	0.8432	0.1340	0.4816	0.079*
C2	0.8669 (2)	0.4816 (2)	0.67397 (13)	0.0583 (4)
H2A	0.7830	0.5704	0.6887	0.087*
H2B	0.9809	0.5306	0.6571	0.087*
H2C	0.8895	0.4262	0.7404	0.087*
C3	0.78588 (18)	0.35520 (17)	0.57518 (11)	0.0433 (3)
C4	0.64805 (18)	0.36396 (16)	0.38885 (11)	0.0420 (3)
C5	0.51881 (17)	0.23873 (16)	0.40821 (10)	0.0384 (3)
C6	0.49111 (17)	0.21600 (16)	0.52166 (10)	0.0393 (3)
C7	0.41364 (17)	0.14044 (16)	0.32061 (10)	0.0401 (3)
H7	0.3322	0.0579	0.3385	0.048*
C8	0.32676 (17)	0.04147 (17)	0.12053 (10)	0.0412 (3)
C9	0.2809 (2)	−0.12053 (18)	0.12899 (12)	0.0502 (3)
H9	0.3068	−0.1605	0.1986	0.060*
C10	0.1953 (2)	−0.2285 (2)	0.03460 (14)	0.0598 (4)
H10	0.1584	−0.3399	0.0416	0.072*
C11	0.1648 (2)	−0.1750 (2)	−0.06667 (13)	0.0593 (4)
H11	0.1097	−0.2505	−0.1301	0.071*
C12	0.21389 (18)	−0.0086 (2)	−0.07868 (11)	0.0495 (4)
C13	0.1908 (2)	0.0502 (3)	−0.18422 (12)	0.0624 (5)
H13	0.1415	−0.0247	−0.2495	0.075*
C14	0.2376 (2)	0.2106 (3)	−0.19338 (13)	0.0663 (5)
H14	0.2247	0.2460	−0.2650	0.080*
C15	0.3050 (2)	0.3242 (2)	−0.09805 (13)	0.0608 (4)
H15	0.3325	0.4378	−0.1047	0.073*
C16	0.3315 (2)	0.2734 (2)	0.00486 (12)	0.0513 (4)
H16	0.3775	0.3521	0.0690	0.062*
C17	0.29151 (17)	0.10513 (18)	0.01706 (10)	0.0428 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0558 (6)	0.0465 (5)	0.0405 (5)	−0.0043 (4)	−0.0028 (4)	0.0094 (4)
O2	0.0450 (5)	0.0633 (6)	0.0309 (5)	−0.0001 (4)	0.0023 (4)	0.0057 (4)
O3	0.0686 (7)	0.0633 (6)	0.0400 (6)	−0.0081 (5)	0.0034 (5)	0.0195 (5)
O4	0.0499 (6)	0.0620 (6)	0.0394 (5)	−0.0027 (5)	0.0111 (4)	0.0081 (4)
N1	0.0441 (6)	0.0532 (7)	0.0315 (6)	0.0003 (5)	0.0015 (4)	0.0076 (5)
C1	0.0452 (8)	0.0568 (8)	0.0550 (9)	0.0065 (6)	−0.0014 (6)	0.0080 (7)
C2	0.0610 (9)	0.0622 (9)	0.0457 (8)	−0.0021 (7)	−0.0061 (7)	−0.0001 (7)
C3	0.0440 (7)	0.0503 (7)	0.0346 (7)	0.0002 (6)	0.0001 (5)	0.0074 (5)
C4	0.0478 (7)	0.0433 (7)	0.0349 (7)	0.0044 (5)	0.0014 (5)	0.0081 (5)
C5	0.0398 (7)	0.0448 (7)	0.0311 (6)	0.0056 (5)	0.0023 (5)	0.0079 (5)
C6	0.0398 (7)	0.0447 (7)	0.0335 (6)	0.0069 (5)	0.0037 (5)	0.0055 (5)
C7	0.0391 (7)	0.0483 (7)	0.0341 (6)	0.0060 (5)	0.0047 (5)	0.0087 (5)
C8	0.0357 (6)	0.0547 (8)	0.0322 (6)	0.0057 (5)	0.0033 (5)	0.0030 (5)
C9	0.0539 (8)	0.0557 (8)	0.0414 (7)	0.0080 (6)	0.0071 (6)	0.0062 (6)
C10	0.0617 (10)	0.0548 (9)	0.0594 (10)	0.0020 (7)	0.0080 (7)	−0.0026 (7)
C11	0.0517 (9)	0.0699 (10)	0.0475 (9)	0.0058 (7)	−0.0028 (7)	−0.0136 (7)
C12	0.0386 (7)	0.0714 (9)	0.0354 (7)	0.0127 (6)	0.0010 (5)	−0.0017 (6)
C13	0.0523 (9)	0.0978 (13)	0.0327 (7)	0.0195 (8)	−0.0036 (6)	−0.0017 (8)
C14	0.0590 (10)	0.1060 (14)	0.0386 (8)	0.0215 (9)	0.0055 (7)	0.0229 (9)
C15	0.0567 (9)	0.0829 (11)	0.0477 (9)	0.0095 (8)	0.0052 (7)	0.0246 (8)
C16	0.0489 (8)	0.0663 (9)	0.0391 (7)	0.0034 (7)	0.0023 (6)	0.0119 (6)
C17	0.0343 (6)	0.0622 (8)	0.0315 (6)	0.0089 (6)	0.0040 (5)	0.0044 (6)

O1—C4	1.3622 (15)	C7—H7	0.9500
O1—C3	1.4403 (15)	C8—C9	1.362 (2)
O2—C6	1.3632 (15)	C8—C17	1.4271 (18)
O2—C3	1.4405 (16)	C9—C10	1.405 (2)
O3—C4	1.2142 (15)	C9—H9	0.9500
O4—C6	1.2072 (15)	C10—C11	1.360 (2)
N1—C7	1.3229 (16)	C10—H10	0.9500
N1—C8	1.4170 (16)	C11—C12	1.413 (2)
N1—H1	0.920 (18)	C11—H11	0.9500
C1—C3	1.510 (2)	C12—C17	1.4204 (19)
C1—H1A	0.9800	C12—C13	1.425 (2)
C1—H1B	0.9800	C13—C14	1.353 (3)
C1—H1C	0.9800	C13—H13	0.9500
C2—C3	1.5063 (19)	C14—C15	1.396 (2)
C2—H2A	0.9800	C14—H14	0.9500
C2—H2B	0.9800	C15—C16	1.367 (2)
C2—H2C	0.9800	C15—H15	0.9500
C4—C5	1.4345 (18)	C16—C17	1.414 (2)
C5—C7	1.3743 (17)	C16—H16	0.9500
C5—C6	1.4508 (17)
C4—O1—C3	116.84 (10)	N1—C7—H7	117.6
C6—O2—C3	118.48 (10)	C5—C7—H7	117.6
C7—N1—C8	126.21 (12)	C9—C8—N1	121.29 (12)
C7—N1—H1	113.8 (11)	C9—C8—C17	121.54 (12)
C8—N1—H1	119.7 (11)	N1—C8—C17	117.13 (12)
C3—C1—H1A	109.5	C8—C9—C10	119.85 (14)
C3—C1—H1B	109.5	C8—C9—H9	120.1
H1A—C1—H1B	109.5	C10—C9—H9	120.1
C3—C1—H1C	109.5	C11—C10—C9	120.64 (15)
H1A—C1—H1C	109.5	C11—C10—H10	119.7
H1B—C1—H1C	109.5	C9—C10—H10	119.7
C3—C2—H2A	109.5	C10—C11—C12	120.82 (14)
C3—C2—H2B	109.5	C10—C11—H11	119.6
H2A—C2—H2B	109.5	C12—C11—H11	119.6
C3—C2—H2C	109.5	C11—C12—C17	119.39 (13)
H2A—C2—H2C	109.5	C11—C12—C13	122.49 (14)
H2B—C2—H2C	109.5	C17—C12—C13	118.11 (15)
O1—C3—O2	110.06 (10)	C14—C13—C12	121.36 (15)
O1—C3—C2	106.69 (11)	C14—C13—H13	119.3
O2—C3—C2	105.71 (11)	C12—C13—H13	119.3
O1—C3—C1	109.85 (11)	C13—C14—C15	120.28 (15)
O2—C3—C1	110.62 (11)	C13—C14—H14	119.9
C2—C3—C1	113.75 (12)	C15—C14—H14	119.9
O3—C4—O1	118.14 (12)	C16—C15—C14	120.52 (16)
O3—C4—C5	125.52 (12)	C16—C15—H15	119.7
O1—C4—C5	116.31 (11)	C14—C15—H15	119.7
C7—C5—C4	121.36 (11)	C15—C16—C17	120.84 (15)
C7—C5—C6	117.92 (11)	C15—C16—H16	119.6
C4—C5—C6	120.69 (11)	C17—C16—H16	119.6
O4—C6—O2	118.28 (11)	C16—C17—C12	118.73 (13)
O4—C6—C5	125.74 (12)	C16—C17—C8	123.65 (12)
O2—C6—C5	115.95 (11)	C12—C17—C8	117.61 (13)
N1—C7—C5	124.76 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.920 (18)	1.982 (18)	2.7130 (16)	135.2 (15)
C1—H1C···O4i	0.98	2.60	3.3709 (19)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.920 (18)	1.982 (18)	2.7130 (16)	135.2 (15)
C1—H1C⋯O4i	0.98	2.60	3.3709 (19)	136

Symmetry code: (i) .