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

In the title compound, C₁₁H₁₂N₂O₄S, the thia­zole ring is nearly planar. The 1,3-dioxane-4,6-dione ring exhibits a half-chair conformation. The NH group forms an intra­molecular contact to a carbonyl O atom, forming a six-membered ring, and an inter­molecular N—H...O hydrogen bond, with an H...O distance of 2.16 Å, is also observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.125
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT322_ALERT_2_C Check Hybridisation of  S15    in Main Residue .          ?
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C16

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

   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1993); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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-[(4-Methylthiazol-2-ylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Crystal data

C11H12N2O4S	F(000) = 560
Mr = 268.29	Dx = 1.467 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 5.6384 (6) Å	θ = 9.0–18.1°
b = 18.562 (4) Å	µ = 0.28 mm^−1
c = 11.920 (2) Å	T = 293 K
β = 103.14 (1)°	Irregular block, yellow
V = 1214.9 (3) Å^3	0.36 × 0.26 × 0.23 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.024
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 2.1°
Graphite monochromator	h = −6→6
ω–2θ scans	k = −22→0
2249 measured reflections	l = −14→0
2144 independent reflections	3 standard reflections every 200 reflections
1590 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0636P)^2 + 0.5695P] where P = (Fo^2 + 2Fc^2)/3
2144 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	0.6130 (4)	0.44825 (11)	0.87611 (17)	0.0399 (5)
H1	0.7383	0.4752	0.9159	0.048*
C2	0.6299 (4)	0.37706 (13)	0.8750 (2)	0.0378 (6)
H2	0.4930	0.3525	0.8348	0.045*
C3	0.8251 (4)	0.33528 (12)	0.9259 (2)	0.0354 (5)
C4	1.0554 (4)	0.36429 (13)	0.9873 (2)	0.0366 (6)
O1	1.1004 (3)	0.42787 (9)	1.00060 (16)	0.0494 (5)
O5	1.2340 (3)	0.31578 (9)	1.02803 (15)	0.0410 (4)
C6	1.1603 (4)	0.24468 (12)	1.0553 (2)	0.0356 (5)
O7	0.9850 (3)	0.21605 (8)	0.95918 (14)	0.0392 (4)
C8	0.8004 (4)	0.25821 (12)	0.90271 (19)	0.0349 (5)
O2	0.6342 (3)	0.22923 (9)	0.83563 (15)	0.0486 (5)
C9	1.0561 (4)	0.24834 (14)	1.1612 (2)	0.0438 (6)
H9A	1.1763	0.2675	1.2244	0.066*
H9B	1.0105	0.2009	1.1803	0.066*
H9C	0.9153	0.2790	1.1462	0.066*
C10	1.3805 (4)	0.19698 (15)	1.0695 (2)	0.0469 (6)
H10A	1.5046	0.2137	1.1332	0.070*
H10B	1.4409	0.1984	1.0004	0.070*
H10C	1.3366	0.1484	1.0837	0.070*
C11	0.4052 (4)	0.48290 (13)	0.8106 (2)	0.0376 (6)
N12	0.2238 (4)	0.44823 (11)	0.74848 (17)	0.0410 (5)
C13	0.0511 (5)	0.49624 (14)	0.6908 (2)	0.0417 (6)
C14	0.1091 (5)	0.56560 (15)	0.7109 (2)	0.0560 (8)
H14	0.0108	0.6039	0.6785	0.067*
S15	0.38807 (14)	0.57493 (4)	0.80431 (7)	0.0602 (3)
C16	−0.1768 (5)	0.46762 (17)	0.6123 (3)	0.0599 (8)
H16A	−0.1738	0.4159	0.6137	0.090*
H16B	−0.1854	0.4842	0.5351	0.090*
H16C	−0.3165	0.4845	0.6379	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0418 (12)	0.0322 (11)	0.0404 (12)	−0.0011 (9)	−0.0014 (9)	0.0001 (9)
C2	0.0420 (13)	0.0341 (13)	0.0345 (13)	−0.0016 (10)	0.0032 (11)	0.0000 (10)
C3	0.0388 (13)	0.0306 (12)	0.0336 (12)	−0.0023 (10)	0.0015 (10)	0.0009 (10)
C4	0.0410 (13)	0.0309 (13)	0.0363 (13)	−0.0020 (11)	0.0057 (10)	0.0009 (10)
O1	0.0536 (11)	0.0312 (10)	0.0572 (12)	−0.0080 (8)	−0.0001 (9)	−0.0031 (8)
O5	0.0329 (8)	0.0332 (9)	0.0523 (11)	−0.0061 (7)	0.0002 (8)	0.0023 (8)
C6	0.0338 (12)	0.0326 (12)	0.0358 (13)	−0.0029 (10)	−0.0014 (10)	0.0008 (10)
O7	0.0420 (9)	0.0294 (9)	0.0396 (10)	0.0003 (7)	−0.0043 (8)	−0.0026 (7)
C8	0.0369 (12)	0.0331 (12)	0.0317 (12)	−0.0026 (10)	0.0020 (10)	0.0000 (10)
O2	0.0498 (11)	0.0390 (10)	0.0455 (10)	−0.0048 (8)	−0.0133 (9)	−0.0043 (8)
C9	0.0416 (14)	0.0475 (15)	0.0397 (14)	−0.0024 (12)	0.0038 (11)	0.0006 (12)
C10	0.0397 (14)	0.0443 (15)	0.0538 (16)	0.0066 (11)	0.0048 (12)	0.0033 (12)
C11	0.0426 (14)	0.0327 (13)	0.0350 (13)	0.0019 (11)	0.0033 (11)	0.0004 (10)
N12	0.0443 (12)	0.0353 (11)	0.0406 (12)	0.0011 (9)	0.0039 (10)	0.0007 (9)
C13	0.0422 (14)	0.0437 (15)	0.0358 (13)	0.0034 (11)	0.0021 (11)	0.0003 (11)
C14	0.0591 (18)	0.0411 (16)	0.0558 (18)	0.0110 (13)	−0.0115 (14)	0.0041 (13)
S15	0.0642 (5)	0.0322 (4)	0.0689 (5)	0.0031 (3)	−0.0171 (4)	−0.0032 (3)
C16	0.0512 (17)	0.064 (2)	0.0574 (18)	−0.0005 (14)	−0.0027 (14)	−0.0019 (15)

Geometric parameters (Å, º)

N1—C2	1.325 (3)	C9—H9B	0.9600
N1—C11	1.407 (3)	C9—H9C	0.9600
N1—H1	0.9063	C10—H10A	0.9600
C2—C3	1.370 (3)	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C3—C4	1.442 (3)	C11—N12	1.290 (3)
C3—C8	1.458 (3)	C11—S15	1.712 (2)
C4—O1	1.210 (3)	N12—C13	1.382 (3)
C4—O5	1.356 (3)	C13—C14	1.337 (4)
O5—C6	1.443 (3)	C13—C16	1.504 (3)
C6—O7	1.435 (3)	C14—S15	1.717 (3)
C6—C10	1.503 (3)	C14—H14	0.9300
C6—C9	1.510 (3)	C16—H16A	0.9600
O7—C8	1.353 (3)	C16—H16B	0.9600
C8—O2	1.211 (3)	C16—H16C	0.9600
C9—H9A	0.9600
C2—N1—C11	120.2 (2)	C6—C9—H9C	109.5
C2—N1—H1	120.4	H9A—C9—H9C	109.5
C11—N1—H1	119.4	H9B—C9—H9C	109.5
N1—C2—C3	127.8 (2)	C6—C10—H10A	109.5
N1—C2—H2	116.1	C6—C10—H10B	109.5
C3—C2—H2	116.1	H10A—C10—H10B	109.5
C2—C3—C4	123.6 (2)	C6—C10—H10C	109.5
C2—C3—C8	116.0 (2)	H10A—C10—H10C	109.5
C4—C3—C8	119.9 (2)	H10B—C10—H10C	109.5
O1—C4—O5	119.0 (2)	N12—C11—N1	122.8 (2)
O1—C4—C3	124.7 (2)	N12—C11—S15	116.30 (18)
O5—C4—C3	116.3 (2)	N1—C11—S15	120.81 (18)
C4—O5—C6	117.34 (17)	C11—N12—C13	109.9 (2)
O7—C6—O5	109.89 (17)	C14—C13—N12	114.6 (2)
O7—C6—C10	105.8 (2)	C14—C13—C16	126.3 (2)
O5—C6—C10	106.91 (19)	N12—C13—C16	119.2 (2)
O7—C6—C9	110.87 (19)	C13—C14—S15	111.4 (2)
O5—C6—C9	109.5 (2)	C13—C14—H14	124.3
C10—C6—C9	113.7 (2)	S15—C14—H14	124.3
C8—O7—C6	119.71 (18)	C11—S15—C14	87.83 (13)
O2—C8—O7	117.6 (2)	C13—C16—H16A	109.5
O2—C8—C3	126.0 (2)	C13—C16—H16B	109.5
O7—C8—C3	116.35 (19)	H16A—C16—H16B	109.5
C6—C9—H9A	109.5	C13—C16—H16C	109.5
C6—C9—H9B	109.5	H16A—C16—H16C	109.5
H9A—C9—H9B	109.5	H16B—C16—H16C	109.5
C11—N1—C2—C3	174.5 (2)	C6—O7—C8—C3	14.4 (3)
N1—C2—C3—C4	−2.7 (4)	C2—C3—C8—O2	6.7 (4)
N1—C2—C3—C8	−175.1 (2)	C4—C3—C8—O2	−165.9 (2)
C2—C3—C4—O1	0.2 (4)	C2—C3—C8—O7	−175.5 (2)
C8—C3—C4—O1	172.3 (2)	C4—C3—C8—O7	11.9 (3)
C2—C3—C4—O5	−176.9 (2)	C2—N1—C11—N12	0.7 (4)
C8—C3—C4—O5	−4.8 (3)	C2—N1—C11—S15	−176.10 (19)
O1—C4—O5—C6	154.7 (2)	N1—C11—N12—C13	−177.8 (2)
C3—C4—O5—C6	−28.0 (3)	S15—C11—N12—C13	−0.8 (3)
C4—O5—C6—O7	51.8 (3)	C11—N12—C13—C14	0.4 (3)
C4—O5—C6—C10	166.2 (2)	C11—N12—C13—C16	179.7 (2)
C4—O5—C6—C9	−70.2 (2)	N12—C13—C14—S15	0.2 (3)
O5—C6—O7—C8	−44.6 (3)	C16—C13—C14—S15	−179.0 (2)
C10—C6—O7—C8	−159.7 (2)	N12—C11—S15—C14	0.8 (2)
C9—C6—O7—C8	76.6 (3)	N1—C11—S15—C14	177.8 (2)
C6—O7—C8—O2	−167.6 (2)	C13—C14—S15—C11	−0.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.91	2.24	2.836 (3)	123
N1—H1···O1^i	0.91	2.16	2.996 (3)	154

Symmetry code: (i) −x+2, −y+1, −z+2.