2,2-Dimethyl-5-(pyrrolidin-2-yl­idene)-1,3-dioxane-4,6-dione

This work describes the first solid-state structural study of a cyclic enaminone derivative from Meldrum's acid, C₁₀H₁₃NO₄. The packing shows an infinite linear chain along [1] mediated by dimeric N—H...O and nonclassical C—H...O hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.056
• wR factor = 0.185
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         300 Deg.

   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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

2,2-Dimethyl-5-(pyrrolidin-2-ylidene)-1,3-dioxane-4,6-dione

Crystal data

C10H13NO4	Z = 2
Mr = 211.21	F(000) = 224
Triclinic, P1	Dx = 1.376 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5947 (3) Å	Cell parameters from 1818 reflections
b = 9.1093 (5) Å	θ = 1.0–26.4°
c = 10.3306 (5) Å	µ = 0.11 mm^−1
α = 90.988 (3)°	T = 296 K
β = 92.799 (3)°	Prism, colorless
γ = 104.114 (3)°	0.18 × 0.15 × 0.10 mm
V = 509.75 (5) Å^3

Data collection

Nonius KappaCCD diffractometer	Rint = 0.026
CCD rotation images, thick slices scans	θmax = 26.4°, θmin = 2.0°
3639 measured reflections	h = −6→6
2053 independent reflections	k = −11→11
1305 reflections with I > 2σ(I)	l = −12→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.056	w = 1/[σ^2(Fo^2) + (0.1141P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.185	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.33 e Å^−3
2053 reflections	Δρmin = −0.26 e Å^−3
138 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C5	0.1379 (4)	0.2275 (2)	0.66830 (19)	0.0446 (5)
O3	0.4654 (3)	0.31968 (16)	0.82912 (14)	0.0540 (4)
O9	0.4919 (3)	0.42524 (18)	0.63943 (15)	0.0626 (5)
O1	0.1595 (3)	0.10043 (16)	0.86647 (15)	0.0621 (5)
N11	0.1078 (3)	0.3420 (2)	0.46137 (17)	0.0519 (5)
H11	0.2441	0.4098	0.4753	0.062*
C4	0.3688 (4)	0.3301 (2)	0.70740 (19)	0.0456 (5)
C10	0.0201 (4)	0.2416 (2)	0.54740 (19)	0.0443 (5)
O16	−0.1317 (3)	−0.00601 (18)	0.72008 (16)	0.0745 (6)
C6	0.0389 (4)	0.1018 (2)	0.7487 (2)	0.0524 (6)
C14	−0.2243 (4)	0.1465 (2)	0.4958 (2)	0.0557 (6)
H14A	−0.3499	0.144	0.5578	0.067*
H14B	−0.2142	0.0437	0.4764	0.067*
C2	0.2995 (4)	0.2416 (3)	0.9220 (2)	0.0570 (6)
C7	0.4599 (5)	0.2048 (4)	1.0320 (3)	0.0864 (9)
H7A	0.3583	0.1412	1.0915	0.13*
H7B	0.5489	0.2968	1.0764	0.13*
H7C	0.5747	0.1529	0.9984	0.13*
C12	−0.0422 (4)	0.3306 (3)	0.3403 (2)	0.0633 (6)
H12A	0.033	0.2892	0.2702	0.076*
H12B	−0.0664	0.4286	0.3162	0.076*
C8	0.1329 (5)	0.3384 (3)	0.9637 (3)	0.0775 (8)
H8A	0.0323	0.3556	0.8904	0.116*
H8B	0.231	0.4336	0.9987	0.116*
H8C	0.029	0.2877	1.0289	0.116*
C13	−0.2825 (5)	0.2242 (3)	0.3722 (3)	0.0728 (7)
H13A	−0.3426	0.1502	0.3021	0.087*
H13B	−0.4068	0.2798	0.3867	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C5	0.0472 (12)	0.0386 (10)	0.0417 (12)	−0.0028 (9)	0.0084 (9)	0.0052 (9)
O3	0.0468 (9)	0.0596 (9)	0.0470 (9)	−0.0046 (7)	0.0026 (7)	0.0132 (7)
O9	0.0575 (9)	0.0608 (10)	0.0551 (9)	−0.0141 (7)	0.0028 (7)	0.0172 (7)
O1	0.0706 (10)	0.0511 (9)	0.0539 (10)	−0.0069 (8)	0.0019 (8)	0.0179 (7)
N11	0.0527 (11)	0.0493 (10)	0.0461 (10)	−0.0021 (8)	−0.0001 (8)	0.0068 (8)
C4	0.0458 (11)	0.0427 (11)	0.0444 (12)	0.0022 (9)	0.0071 (9)	0.0082 (9)
C10	0.0461 (11)	0.0392 (10)	0.0441 (12)	0.0025 (9)	0.0095 (9)	0.0002 (9)
O16	0.0834 (12)	0.0560 (10)	0.0626 (11)	−0.0245 (9)	0.0014 (9)	0.0107 (8)
C6	0.0564 (13)	0.0448 (12)	0.0485 (13)	−0.0038 (10)	0.0088 (11)	0.0053 (10)
C14	0.0505 (13)	0.0522 (12)	0.0573 (14)	−0.0007 (10)	0.0025 (10)	−0.0017 (10)
C2	0.0557 (13)	0.0597 (13)	0.0439 (12)	−0.0095 (10)	0.0044 (10)	0.0108 (10)
C7	0.0799 (18)	0.097 (2)	0.0654 (17)	−0.0107 (15)	−0.0090 (14)	0.0364 (15)
C12	0.0714 (16)	0.0626 (14)	0.0510 (14)	0.0085 (12)	−0.0062 (11)	0.0063 (11)
C8	0.0711 (16)	0.0909 (19)	0.0634 (16)	0.0051 (14)	0.0145 (13)	−0.0146 (14)
C13	0.0656 (16)	0.0756 (17)	0.0708 (17)	0.0078 (12)	−0.0137 (13)	0.0066 (13)

Geometric parameters (Å, º)

O1—C2	1.427 (3)	C14—C13	1.529 (4)
O1—C6	1.363 (3)	N11—H11	0.86
O3—C2	1.441 (2)	C7—H7A	0.96
O3—C4	1.358 (2)	C7—H7B	0.96
O9—C4	1.223 (2)	C7—H7C	0.96
O16—C6	1.211 (2)	C8—H8A	0.96
N11—C10	1.311 (3)	C8—H8B	0.96
N11—C12	1.460 (3)	C8—H8C	0.96
C2—C7	1.507 (3)	C12—H12A	0.97
C2—C8	1.503 (3)	C12—H12B	0.97
C5—C4	1.433 (3)	C13—H13A	0.97
C5—C6	1.441 (3)	C13—H13B	0.97
C5—C10	1.406 (3)	C14—H14A	0.97
C10—C14	1.497 (3)	C14—H14B	0.97
C12—C13	1.508 (4)
C6—O1—C2	117.86 (16)	C2—C7—H7B	109.5
C4—O3—C2	117.15 (16)	C2—C7—H7C	109.5
C10—N11—C12	115.23 (18)	C2—C8—H8A	109.5
O1—C2—O3	109.59 (17)	C2—C8—H8B	109.5
O1—C2—C8	110.93 (18)	C2—C8—H8C	109.5
O3—C2—C8	110.1 (2)	N11—C12—H12A	111.2
O1—C2—C7	106.7 (2)	N11—C12—H12B	111.2
O3—C2—C7	106.18 (18)	C13—C12—H12A	111.2
C8—C2—C7	113.2 (2)	C13—C12—H12B	111.2
O9—C4—O3	116.27 (18)	C12—C13—H13A	110.6
O9—C4—C5	125.7 (2)	C14—C13—H13A	110.6
O3—C4—C5	118.03 (17)	C12—C13—H13B	110.6
C4—C5—C6	119.29 (19)	C14—C13—H13B	110.6
C10—C5—C4	120.25 (18)	C10—C14—H14A	110.8
C10—C5—C6	120.23 (18)	C10—C14—H14B	110.8
O16—C6—O1	116.87 (18)	C13—C14—H14A	110.8
O1—C6—C5	116.19 (18)	C13—C14—H14B	110.8
O16—C6—C5	126.8 (2)	H7A—C7—H7B	109.5
N11—C10—C5	125.05 (19)	H7A—C7—H7C	109.5
N11—C10—C14	108.79 (19)	H7B—C7—H7C	109.5
C5—C10—C14	126.16 (18)	H8A—C8—H8B	109.5
N11—C12—C13	103.00 (18)	H8A—C8—H8C	109.5
C12—C13—C14	105.56 (19)	H8B—C8—H8C	109.5
C10—C14—C13	104.53 (19)	H12A—C12—H12B	109.1
C10—N11—H11	122.4	H13A—C13—H13B	108.8
C12—N11—H11	122.4	H14A—C14—H14B	108.9
C2—C7—H7A	109.5
C2—O1—C6—O16	−159.1 (2)	C10—C5—C4—O3	174.77 (16)
C2—O1—C6—C5	24.5 (3)	C10—C5—C4—O9	−7.1 (3)
C6—O1—C2—O3	−51.9 (3)	C4—C5—C6—O1	8.0 (3)
C6—O1—C2—C8	69.9 (2)	C4—C5—C6—O16	−168.0 (2)
C6—O1—C2—C7	−166.42 (18)	C10—C5—C6—O1	−177.51 (16)
C4—O3—C2—O1	48.4 (2)	C10—C5—C6—O16	6.5 (3)
C4—O3—C2—C8	−73.8 (2)	C4—C5—C10—N11	1.8 (3)
C4—O3—C2—C7	163.3 (2)	C6—C5—C10—N11	−172.60 (18)
C2—O3—C4—O9	163.01 (18)	C4—C5—C10—C14	−177.80 (18)
C2—O3—C4—C5	−18.7 (3)	C6—C5—C10—C14	7.8 (3)
C12—N11—C10—C5	177.38 (18)	N11—C10—C14—C13	−8.1 (2)
C12—N11—C10—C14	−3.0 (2)	C5—C10—C14—C13	171.5 (2)
C10—N11—C12—C13	12.8 (3)	N11—C12—C13—C14	−16.6 (2)
C6—C5—C4—O3	−10.8 (3)	C10—C14—C13—C12	15.4 (2)
C6—C5—C4—O9	167.37 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O9	0.86	2.12	2.710 (2)	126
N11—H11···O9^i	0.86	2.24	2.930 (2)	138
C7—H7A···O16^ii	0.96	2.54	3.494 (3)	170

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+2.