2,2-Dimethyl-5-[(pyridin-2-yl-amino)-methyl-idene]-1,3-dioxane-4,6-dione.

In the title compound, C(12)H(12)N(2)O(4), the dihedral angle between the pyridine and enamine planes is 3.5 (3)°, while the angle between the dioxanedione (seven atoms) and enamine planes is 4.6 (3)°. The dioxane ring approximates an envelope conformation.

Related literature

The title compound is an inter­mediate in the synthesis of 4(1H)-quinolone-based drugs. For the synthesis and structures of related anti­tumor precursors, see: Cassis et al. (1985 ▶); Ruchelman et al. (2003 ▶); Shi et al. (2009 ▶).

Experimental

Crystal data

C12H12N2O4

M = 248.24

Monoclinic,

a = 8.7344 (10) Å

b = 13.9712 (15) Å

c = 9.4744 (11) Å

β = 94.601 (11)°

V = 1152.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.22 × 0.18 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Eos CCD detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.997, T max = 1.0

4873 measured reflections

2334 independent reflections

1659 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.096

S = 1.03

2334 reflections

166 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053250/bh2327sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053250/bh2327Isup2.hkl

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

C12H12N2O4	F(000) = 520
Mr = 248.24	Dx = 1.431 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 1780 reflections
a = 8.7344 (10) Å	θ = 3.1–29.2°
b = 13.9712 (15) Å	µ = 0.11 mm−1
c = 9.4744 (11) Å	T = 293 K
β = 94.601 (11)°	Block, colourless
V = 1152.4 (2) Å3	0.22 × 0.18 × 0.16 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with an Eos CCD detector	2334 independent reflections
Radiation source: fine-focus sealed tube	1659 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.4°
ω scans	h = −10→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −17→16
Tmin = 0.997, Tmax = 1.0	l = −11→11
4873 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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0383P)2 + 0.0655P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2334 reflections	Δρmax = 0.14 e Å−3
166 parameters	Δρmin = −0.14 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0060 (9)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O3	0.21039 (13)	0.15916 (7)	0.50800 (11)	0.0497 (3)
O4	0.37760 (12)	0.11610 (7)	0.33485 (12)	0.0504 (3)
C6	0.22965 (17)	−0.10004 (11)	0.49185 (16)	0.0421 (4)
H6	0.1613	−0.1134	0.5596	0.050*
O1	0.10857 (14)	0.05240 (7)	0.64457 (11)	0.0556 (3)
O2	0.44968 (12)	−0.03377 (8)	0.30745 (12)	0.0559 (3)
N2	0.29233 (14)	−0.17386 (8)	0.43038 (13)	0.0455 (3)
H2	0.3571	−0.1614	0.3692	0.055*
C7	0.25719 (16)	−0.00541 (10)	0.46383 (15)	0.0388 (3)
N1	0.17056 (15)	−0.28950 (8)	0.55799 (13)	0.0474 (4)
C1	0.1423 (2)	−0.38227 (11)	0.58158 (18)	0.0532 (4)
H1	0.0776	−0.3976	0.6515	0.064*
C9	0.18429 (18)	0.06634 (10)	0.54492 (16)	0.0428 (4)
C8	0.36562 (17)	0.02142 (11)	0.36380 (16)	0.0434 (4)
C5	0.26224 (16)	−0.27096 (10)	0.45637 (16)	0.0400 (4)
C3	0.2993 (2)	−0.43431 (11)	0.40519 (18)	0.0547 (5)
H3	0.3432	−0.4829	0.3548	0.066*
C4	0.32929 (19)	−0.34013 (11)	0.37743 (17)	0.0487 (4)
H4	0.3930	−0.3233	0.3074	0.058*
C12	0.11654 (19)	0.16341 (11)	0.26210 (16)	0.0493 (4)
H12B	0.1452	0.1783	0.1689	0.074*
H12C	0.0343	0.2048	0.2851	0.074*
H12A	0.0833	0.0980	0.2649	0.074*
C11	0.3145 (2)	0.27839 (11)	0.36841 (19)	0.0606 (5)
H11A	0.3519	0.2923	0.2781	0.091*
H11C	0.3969	0.2843	0.4412	0.091*
H11B	0.2342	0.3226	0.3864	0.091*
C2	0.2036 (2)	−0.45560 (11)	0.50844 (18)	0.0582 (5)
H2A	0.1806	−0.5189	0.5286	0.070*
C10	0.25227 (18)	0.17780 (10)	0.36764 (16)	0.0439 (4)

	U11	U22	U33	U12	U13	U23
O3	0.0704 (8)	0.0405 (6)	0.0386 (6)	−0.0001 (5)	0.0061 (5)	−0.0014 (5)
O4	0.0432 (7)	0.0437 (6)	0.0656 (8)	−0.0011 (5)	0.0137 (5)	0.0085 (5)
C6	0.0384 (9)	0.0485 (9)	0.0395 (9)	0.0012 (7)	0.0042 (7)	−0.0004 (7)
O1	0.0669 (8)	0.0573 (7)	0.0448 (7)	0.0015 (6)	0.0178 (6)	0.0005 (5)
O2	0.0470 (7)	0.0543 (7)	0.0692 (8)	0.0047 (6)	0.0208 (6)	0.0026 (6)
N2	0.0452 (8)	0.0426 (8)	0.0502 (8)	0.0012 (6)	0.0140 (6)	0.0015 (6)
C7	0.0374 (8)	0.0399 (8)	0.0390 (8)	−0.0006 (7)	0.0034 (6)	0.0022 (7)
N1	0.0516 (9)	0.0447 (8)	0.0471 (8)	0.0022 (6)	0.0102 (6)	0.0016 (6)
C1	0.0620 (11)	0.0477 (10)	0.0511 (10)	−0.0035 (9)	0.0121 (8)	0.0056 (8)
C9	0.0460 (9)	0.0445 (9)	0.0373 (9)	−0.0010 (7)	−0.0001 (7)	0.0006 (7)
C8	0.0372 (9)	0.0438 (9)	0.0491 (9)	−0.0005 (7)	0.0020 (7)	0.0017 (7)
C5	0.0376 (8)	0.0403 (9)	0.0418 (9)	−0.0009 (7)	0.0022 (6)	0.0015 (7)
C3	0.0624 (12)	0.0465 (10)	0.0557 (11)	0.0058 (8)	0.0072 (9)	−0.0100 (8)
C4	0.0478 (10)	0.0521 (10)	0.0477 (10)	0.0015 (8)	0.0123 (8)	−0.0025 (7)
C12	0.0534 (10)	0.0523 (9)	0.0422 (10)	0.0029 (8)	0.0047 (7)	0.0012 (7)
C11	0.0704 (13)	0.0451 (10)	0.0651 (12)	−0.0087 (9)	−0.0009 (9)	0.0058 (8)
C2	0.0728 (13)	0.0414 (9)	0.0606 (12)	−0.0031 (9)	0.0069 (9)	0.0017 (8)
C10	0.0495 (10)	0.0411 (9)	0.0419 (9)	−0.0002 (7)	0.0078 (7)	0.0016 (7)

O3—C9	1.3671 (16)	C1—C2	1.370 (2)
O3—C10	1.4311 (18)	C5—C4	1.381 (2)
O4—C8	1.3567 (17)	C3—H3	0.9300
O4—C10	1.4465 (18)	C3—C4	1.371 (2)
C6—H6	0.9300	C3—C2	1.370 (2)
C6—N2	1.3242 (18)	C4—H4	0.9300
C6—C7	1.374 (2)	C12—H12B	0.9600
O1—C9	1.2112 (17)	C12—H12C	0.9600
O2—C8	1.2172 (17)	C12—H12A	0.9600
N2—H2	0.8600	C12—C10	1.502 (2)
N2—C5	1.4072 (18)	C11—H11A	0.9600
C7—C9	1.442 (2)	C11—H11C	0.9600
C7—C8	1.442 (2)	C11—H11B	0.9600
N1—C1	1.3415 (19)	C11—C10	1.507 (2)
N1—C5	1.3263 (18)	C2—H2A	0.9300
C1—H1	0.9300
O3—C9—C7	115.68 (13)	C5—N2—H2	117.1
O3—C10—O4	110.21 (11)	C5—N1—C1	116.06 (13)
O3—C10—C12	110.33 (13)	C5—C4—H4	120.9
O3—C10—C11	106.51 (12)	C3—C4—C5	118.16 (15)
O4—C8—C7	116.85 (13)	C3—C4—H4	120.9
O4—C10—C12	110.35 (12)	C3—C2—C1	118.99 (15)
O4—C10—C11	106.15 (13)	C3—C2—H2A	120.5
C6—N2—H2	117.1	C4—C5—N2	119.12 (13)
C6—N2—C5	125.74 (13)	C4—C3—H3	120.6
C6—C7—C9	118.33 (13)	C12—C10—C11	113.15 (13)
C6—C7—C8	120.77 (14)	H12B—C12—H12C	109.5
O1—C9—O3	117.68 (13)	H12B—C12—H12A	109.5
O1—C9—C7	126.57 (14)	H12C—C12—H12A	109.5
O2—C8—O4	118.03 (13)	H11A—C11—H11C	109.5
O2—C8—C7	125.08 (14)	H11A—C11—H11B	109.5
N2—C6—H6	117.3	H11C—C11—H11B	109.5
N2—C6—C7	125.42 (14)	C2—C1—H1	118.2
C7—C6—H6	117.3	C2—C3—H3	120.6
N1—C1—H1	118.2	C2—C3—C4	118.84 (15)
N1—C1—C2	123.64 (15)	C10—C12—H12B	109.5
N1—C5—N2	116.58 (13)	C10—C12—H12C	109.5
N1—C5—C4	124.30 (14)	C10—C12—H12A	109.5
C1—C2—H2A	120.5	C10—C11—H11A	109.5
C9—O3—C10	118.08 (11)	C10—C11—H11C	109.5
C9—C7—C8	120.72 (13)	C10—C11—H11B	109.5
C8—O4—C10	117.75 (11)
C6—N2—C5—N1	−4.6 (2)	C9—O3—C10—C11	−165.07 (13)
C6—N2—C5—C4	175.96 (15)	C9—C7—C8—O4	−9.6 (2)
C6—C7—C9—O3	−177.16 (12)	C9—C7—C8—O2	168.03 (15)
C6—C7—C9—O1	6.0 (2)	C8—O4—C10—O3	47.99 (17)
C6—C7—C8—O4	175.36 (13)	C8—O4—C10—C12	−74.10 (16)
C6—C7—C8—O2	−7.0 (2)	C8—O4—C10—C11	162.95 (12)
N2—C6—C7—C9	−177.35 (14)	C8—C7—C9—O3	7.7 (2)
N2—C6—C7—C8	−2.2 (2)	C8—C7—C9—O1	−169.19 (15)
N2—C5—C4—C3	179.53 (14)	C5—N1—C1—C2	0.7 (2)
C7—C6—N2—C5	−178.57 (14)	C4—C3—C2—C1	−0.7 (3)
N1—C1—C2—C3	0.0 (3)	C2—C3—C4—C5	0.6 (2)
N1—C5—C4—C3	0.2 (2)	C10—O3—C9—O1	−159.37 (14)
C1—N1—C5—N2	179.83 (13)	C10—O3—C9—C7	23.48 (19)
C1—N1—C5—C4	−0.8 (2)	C10—O4—C8—O2	162.84 (14)
C9—O3—C10—O4	−50.35 (17)	C10—O4—C8—C7	−19.38 (19)
C9—O3—C10—C12	71.76 (16)