2,2-Dimethyl-5-[(6-methyl­pyridin-2-ylamino)methyl­ene]-1,3-dioxane-4,6-dione

In the title compound C₁₃H₁₄N₂O₄, the 1,3-dioxane-4,6-dione ring exhibits an envelope conformation. The amino H atom forms intra- and inter­molecular contacts to carbonyl O atoms. One inter­molecular C—H...O hydrogen bond is also observed.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.129
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT430_ALERT_2_C Short Inter D...A Contact  O4     ..  O4      ..       2.86 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

5-[(6-Methylpyridin-2-ylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Crystal data

C13H14N2O4	F(000) = 1104
Mr = 262.26	Dx = 1.297 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 17.101 (1) Å	θ = 5.2–17.6°
b = 7.354 (1) Å	µ = 0.82 mm^−1
c = 21.375 (2) Å	T = 299 K
β = 91.868 (9)°	Needle, colourless
V = 2686.7 (5) Å^3	0.50 × 0.10 × 0.08 mm
Z = 8

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 66.9°, θmin = 4.1°
Graphite monochromator	h = −20→5
ω/2θ scans	k = −8→0
3300 measured reflections	l = −25→25
2394 independent reflections	3 standard reflections every 120 min
1901 reflections with I > 2σ(I)	intensity decay: 1.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0788P)^2 + 0.4614P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.040
2394 reflections	Δρmax = 0.18 e Å^−3
176 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.14519 (7)	0.85371 (15)	0.21935 (5)	0.0520 (3)
O2	0.07549 (7)	1.06907 (15)	0.15870 (5)	0.0472 (3)
O3	0.16740 (11)	0.57687 (18)	0.18520 (7)	0.0864 (6)
O4	0.02914 (8)	1.00502 (16)	0.06353 (5)	0.0573 (4)
N1	0.12356 (8)	0.40659 (18)	−0.02682 (6)	0.0474 (4)
N2	0.07897 (8)	0.68765 (17)	0.00771 (6)	0.0458 (4)
H2N	0.0534	0.7863	0.0001	0.055*
C1	0.08430 (9)	0.5576 (2)	−0.04122 (7)	0.0433 (4)
C2	0.04955 (11)	0.5945 (2)	−0.09877 (8)	0.0545 (5)
H2	0.0228	0.7027	−0.1065	0.065*
C3	0.05624 (12)	0.4635 (3)	−0.14454 (8)	0.0599 (5)
H3	0.0338	0.4820	−0.1843	0.072*
C4	0.09619 (11)	0.3056 (3)	−0.13106 (9)	0.0576 (5)
H4	0.1011	0.2165	−0.1616	0.069*
C5	0.12906 (10)	0.2799 (2)	−0.07178 (8)	0.0508 (4)
C6	0.11099 (10)	0.6655 (2)	0.06397 (8)	0.0458 (4)
H6	0.1370	0.5562	0.0714	0.055*
C7	0.11024 (9)	0.7860 (2)	0.11295 (7)	0.0425 (4)
C8	0.14381 (11)	0.7275 (2)	0.17272 (8)	0.0525 (5)
C9	0.14081 (10)	1.0427 (2)	0.20170 (7)	0.0438 (4)
C10	0.06979 (9)	0.9580 (2)	0.10813 (7)	0.0417 (4)
C11	0.17319 (13)	0.1101 (3)	−0.05424 (11)	0.0717 (6)
H11A	0.2276	0.1385	−0.0476	0.108*	0.50
H11B	0.1672	0.0225	−0.0874	0.108*	0.50
H11C	0.1529	0.0606	−0.0165	0.108*	0.50
H11D	0.1376	0.0093	−0.0534	0.108*	0.50
H11E	0.1980	0.1252	−0.0136	0.108*	0.50
H11F	0.2123	0.0871	−0.0845	0.108*	0.50
C12	0.12296 (12)	1.1473 (3)	0.25979 (8)	0.0605 (5)
H12A	0.1184	1.2743	0.2499	0.091*
H12B	0.1644	1.1300	0.2906	0.091*
H12C	0.0746	1.1047	0.2761	0.091*
C13	0.21556 (11)	1.1022 (3)	0.17316 (9)	0.0611 (5)
H13A	0.2584	1.0829	0.2026	0.092*
H13B	0.2123	1.2290	0.1627	0.092*
H13C	0.2239	1.0327	0.1359	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0781 (8)	0.0331 (6)	0.0439 (6)	0.0000 (6)	−0.0107 (5)	0.0058 (5)
O2	0.0578 (7)	0.0362 (6)	0.0469 (6)	0.0094 (5)	−0.0083 (5)	−0.0043 (5)
O3	0.1409 (14)	0.0345 (7)	0.0807 (10)	0.0192 (8)	−0.0449 (10)	0.0026 (7)
O4	0.0758 (8)	0.0438 (7)	0.0509 (6)	0.0158 (6)	−0.0195 (6)	−0.0002 (5)
N1	0.0543 (8)	0.0340 (7)	0.0540 (8)	0.0009 (6)	0.0021 (6)	−0.0029 (6)
N2	0.0586 (8)	0.0291 (7)	0.0495 (8)	0.0034 (6)	−0.0041 (6)	−0.0021 (6)
C1	0.0508 (9)	0.0302 (8)	0.0490 (9)	−0.0026 (7)	0.0029 (7)	−0.0016 (6)
C2	0.0713 (12)	0.0401 (9)	0.0516 (9)	0.0010 (8)	−0.0046 (8)	0.0004 (7)
C3	0.0773 (12)	0.0550 (11)	0.0473 (10)	−0.0069 (10)	−0.0020 (9)	−0.0018 (8)
C4	0.0699 (12)	0.0471 (10)	0.0564 (10)	−0.0101 (9)	0.0112 (9)	−0.0141 (8)
C5	0.0565 (10)	0.0344 (9)	0.0621 (10)	−0.0044 (7)	0.0112 (8)	−0.0073 (7)
C6	0.0542 (9)	0.0297 (8)	0.0532 (9)	0.0007 (7)	−0.0042 (7)	0.0005 (7)
C7	0.0499 (9)	0.0292 (8)	0.0480 (9)	0.0008 (6)	−0.0059 (7)	0.0015 (6)
C8	0.0711 (11)	0.0314 (8)	0.0539 (10)	0.0012 (8)	−0.0136 (8)	0.0040 (7)
C9	0.0575 (10)	0.0297 (8)	0.0437 (8)	0.0002 (7)	−0.0073 (7)	0.0027 (6)
C10	0.0494 (9)	0.0341 (8)	0.0412 (8)	−0.0001 (7)	−0.0039 (7)	0.0009 (6)
C11	0.0855 (14)	0.0397 (10)	0.0901 (15)	0.0107 (10)	0.0074 (12)	−0.0094 (10)
C12	0.0824 (13)	0.0499 (11)	0.0488 (10)	0.0039 (9)	−0.0065 (9)	−0.0080 (8)
C13	0.0640 (12)	0.0544 (11)	0.0647 (11)	−0.0140 (9)	−0.0009 (9)	−0.0033 (9)

Geometric parameters (Å, º)

O1—C8	1.361 (2)	C6—C7	1.372 (2)
O1—C9	1.4417 (18)	C6—H6	0.9300
O2—C10	1.3558 (18)	C7—C10	1.444 (2)
O2—C9	1.4364 (19)	C7—C8	1.449 (2)
O3—C8	1.206 (2)	C9—C12	1.500 (2)
O4—C10	1.2117 (18)	C9—C13	1.499 (3)
N1—C1	1.328 (2)	C11—H11A	0.9600
N1—C5	1.344 (2)	C11—H11B	0.9600
N2—C6	1.315 (2)	C11—H11C	0.9600
N2—C1	1.423 (2)	C11—H11D	0.9600
N2—H2N	0.8600	C11—H11E	0.9600
C1—C2	1.376 (2)	C11—H11F	0.9600
C2—C3	1.381 (2)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.373 (3)	C12—H12C	0.9600
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.382 (3)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C11	1.500 (3)
C8—O1—C9	117.79 (12)	O4—C10—O2	118.68 (14)
C10—O2—C9	117.60 (12)	O4—C10—C7	124.57 (14)
C1—N1—C5	117.40 (14)	O2—C10—C7	116.68 (13)
C6—N2—C1	123.67 (14)	C5—C11—H11A	109.5
C6—N2—H2N	118.2	C5—C11—H11B	109.5
C1—N2—H2N	118.2	H11A—C11—H11B	109.5
N1—C1—C2	124.93 (15)	C5—C11—H11C	109.5
N1—C1—N2	115.83 (14)	H11A—C11—H11C	109.5
C2—C1—N2	119.24 (15)	H11B—C11—H11C	109.5
C1—C2—C3	116.91 (17)	C5—C11—H11D	109.5
C1—C2—H2	121.5	H11A—C11—H11D	141.1
C3—C2—H2	121.5	H11B—C11—H11D	56.3
C4—C3—C2	119.58 (17)	H11C—C11—H11D	56.3
C4—C3—H3	120.2	C5—C11—H11E	109.5
C2—C3—H3	120.2	H11A—C11—H11E	56.3
C3—C4—C5	119.51 (16)	H11B—C11—H11E	141.1
C3—C4—H4	120.2	H11C—C11—H11E	56.3
C5—C4—H4	120.2	H11D—C11—H11E	109.5
N1—C5—C4	121.67 (16)	C5—C11—H11F	109.5
N1—C5—C11	116.39 (16)	H11A—C11—H11F	56.3
C4—C5—C11	121.94 (16)	H11B—C11—H11F	56.3
N2—C6—C7	127.16 (15)	H11C—C11—H11F	141.1
N2—C6—H6	116.4	H11D—C11—H11F	109.5
C7—C6—H6	116.4	H11E—C11—H11F	109.5
C6—C7—C10	121.85 (14)	C9—C12—H12A	109.5
C6—C7—C8	117.89 (14)	C9—C12—H12B	109.5
C10—C7—C8	119.89 (14)	H12A—C12—H12B	109.5
O3—C8—O1	117.82 (15)	C9—C12—H12C	109.5
O3—C8—C7	126.01 (16)	H12A—C12—H12C	109.5
O1—C8—C7	116.11 (14)	H12B—C12—H12C	109.5
O2—C9—O1	109.27 (12)	C9—C13—H13A	109.5
O2—C9—C12	106.58 (13)	C9—C13—H13B	109.5
O1—C9—C12	106.75 (13)	H13A—C13—H13B	109.5
O2—C9—C13	110.85 (13)	C9—C13—H13C	109.5
O1—C9—C13	110.48 (14)	H13A—C13—H13C	109.5
C12—C9—C13	112.73 (15)	H13B—C13—H13C	109.5
C5—N1—C1—C2	−0.6 (3)	C6—C7—C8—O3	−6.0 (3)
C5—N1—C1—N2	179.34 (14)	C10—C7—C8—O3	167.1 (2)
C6—N2—C1—N1	0.9 (2)	C6—C7—C8—O1	177.10 (15)
C6—N2—C1—C2	−179.19 (16)	C10—C7—C8—O1	−9.7 (2)
N1—C1—C2—C3	0.2 (3)	C10—O2—C9—O1	−51.27 (17)
N2—C1—C2—C3	−179.79 (15)	C10—O2—C9—C12	−166.27 (14)
C1—C2—C3—C4	0.1 (3)	C10—O2—C9—C13	70.72 (17)
C2—C3—C4—C5	0.1 (3)	C8—O1—C9—O2	51.04 (19)
C1—N1—C5—C4	0.8 (2)	C8—O1—C9—C12	165.94 (15)
C1—N1—C5—C11	−179.58 (16)	C8—O1—C9—C13	−71.17 (19)
C3—C4—C5—N1	−0.6 (3)	C9—O2—C10—O4	−160.70 (14)
C3—C4—C5—C11	179.84 (18)	C9—O2—C10—C7	22.32 (19)
C1—N2—C6—C7	178.15 (15)	C6—C7—C10—O4	5.6 (3)
N2—C6—C7—C10	2.0 (3)	C8—C7—C10—O4	−167.27 (16)
N2—C6—C7—C8	174.99 (17)	C6—C7—C10—O2	−177.60 (14)
C9—O1—C8—O3	161.11 (18)	C8—C7—C10—O2	9.5 (2)
C9—O1—C8—C7	−21.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O4	0.86	2.15	2.7683 (18)	128
N2—H2N···O4^i	0.86	2.46	3.2652 (18)	155
C2—H2···O4^i	0.93	2.51	3.335 (2)	148

Symmetry code: (i) −x, −y+2, −z.