5-(5-Bromo­thia­zol-2-ylamino­methyl­ene)-2,2-dimethyl-1,3-dioxane-4,6-dione

In the title compound, C₁₀H₉BrN₂O₄S, the 1,3-dioxane-4,6-dione ring exhibits a sofa conformation. The thia­zole ring is nearly planar. The amino H atom has an intra­molecular N—H...O contact, forming a six-membered ring, and an inter­molecular hydrogen bond to a carbonyl O is also observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.041
• wR factor = 0.103
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
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  S1     in Main Residue .          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT430_ALERT_2_C Short Inter D...A Contact  O9     ..  O9      ..       2.88 Ang.

   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

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

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Computing details

Data collection: CAD-4-PC Software (Nonius, 1993); cell refinement: CAD-4-PC Software; 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-(5-Bromothiazol-2-ylaminomethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione ?

Crystal data

C10H9BrN2O4S	F(000) = 664
Mr = 333.16	Dx = 1.763 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 5.408 (5) Å	θ = 5.5–23.7°
b = 18.013 (5) Å	µ = 3.45 mm^−1
c = 13.114 (5) Å	T = 293 K
β = 100.717 (5)°	Prism, colorless
V = 1255.2 (13) Å^3	0.50 × 0.16 × 0.13 mm
Z = 4

Data collection

Nonius CAD-4 diffractometer	1269 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 25.1°, θmin = 1.9°
ω/2θ scans	h = −6→6
Absorption correction: ψ scan (North et al., 1968)	k = −21→0
Tmin = 0.504, Tmax = 0.641	l = −15→0
2330 measured reflections	3 standard reflections every 200 reflections
2230 independent reflections	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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0483P)^2 + 0.077P] where P = (Fo^2 + 2Fc^2)/3
2230 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.28 e Å^−3
1 restraint	Δρmin = −0.48 e Å^−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
Br1	0.60744 (10)	0.10113 (4)	0.50491 (4)	0.0727 (3)
S1	0.3249 (2)	0.06002 (7)	0.28108 (9)	0.0499 (3)
C2	0.3340 (8)	0.1086 (3)	0.3947 (3)	0.0434 (12)
C3	0.1310 (9)	0.1510 (3)	0.3909 (3)	0.0482 (12)
H3	0.1059	0.1808	0.4460	0.058*
N4	−0.0394 (7)	0.1471 (2)	0.2984 (3)	0.0484 (10)
C5	0.0381 (8)	0.1015 (2)	0.2354 (3)	0.0382 (10)
N6	−0.0978 (7)	0.0881 (2)	0.1359 (3)	0.0381 (9)
H6	−0.0356	0.0563	0.0979	0.032 (12)*
C7	−0.3038 (8)	0.1264 (2)	0.0990 (3)	0.0386 (11)
H7	−0.3558	0.1601	0.1444	0.046*
C8	−0.4496 (8)	0.1224 (2)	0.0020 (3)	0.0372 (11)
C9	−0.3958 (8)	0.0722 (3)	−0.0760 (3)	0.0387 (11)
O9	−0.2342 (6)	0.02496 (17)	−0.0615 (2)	0.0523 (9)
O10	−0.5432 (6)	0.07783 (16)	−0.1706 (2)	0.0468 (8)
C11	−0.6807 (8)	0.1463 (3)	−0.1967 (3)	0.0418 (12)
O12	−0.8108 (5)	0.16634 (16)	−0.1156 (2)	0.0431 (8)
C13	−0.6782 (8)	0.1672 (3)	−0.0166 (3)	0.0398 (11)
O13	−0.7631 (6)	0.20151 (18)	0.0477 (2)	0.0541 (9)
C111	−0.5033 (9)	0.2070 (3)	−0.2158 (4)	0.0526 (13)
H11A	−0.4177	0.1922	−0.2704	0.079*
H11B	−0.3823	0.2158	−0.1535	0.079*
H11C	−0.5968	0.2517	−0.2355	0.079*
C112	−0.8795 (9)	0.1291 (3)	−0.2904 (4)	0.0641 (16)
H11D	−0.8003	0.1154	−0.3474	0.096*
H11E	−0.9828	0.1721	−0.3089	0.096*
H11F	−0.9821	0.0888	−0.2747	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0586 (3)	0.1134 (6)	0.0387 (3)	−0.0064 (3)	−0.0097 (2)	−0.0026 (3)
S1	0.0520 (7)	0.0602 (8)	0.0329 (6)	0.0097 (6)	−0.0040 (5)	−0.0049 (6)
C2	0.047 (3)	0.050 (3)	0.029 (2)	−0.010 (3)	−0.003 (2)	0.001 (2)
C3	0.053 (3)	0.057 (3)	0.034 (3)	−0.004 (3)	0.006 (2)	−0.012 (2)
N4	0.052 (2)	0.056 (3)	0.034 (2)	0.004 (2)	0.0017 (18)	−0.009 (2)
C5	0.045 (3)	0.040 (3)	0.029 (2)	−0.003 (2)	0.0045 (19)	0.001 (2)
N6	0.047 (2)	0.036 (2)	0.0279 (18)	0.0048 (19)	−0.0008 (16)	−0.0054 (18)
C7	0.047 (3)	0.033 (3)	0.036 (2)	−0.001 (2)	0.009 (2)	−0.001 (2)
C8	0.040 (3)	0.038 (3)	0.032 (2)	0.002 (2)	0.004 (2)	0.002 (2)
C9	0.037 (3)	0.040 (3)	0.036 (3)	−0.004 (2)	0.001 (2)	−0.001 (2)
O9	0.0549 (19)	0.047 (2)	0.048 (2)	0.0216 (18)	−0.0067 (16)	−0.0069 (16)
O10	0.0540 (18)	0.045 (2)	0.0348 (17)	0.0119 (15)	−0.0093 (15)	−0.0073 (14)
C11	0.040 (3)	0.053 (3)	0.030 (2)	0.010 (2)	0.001 (2)	−0.003 (2)
O12	0.0345 (16)	0.060 (2)	0.0339 (18)	0.0069 (15)	0.0046 (14)	0.0050 (15)
C13	0.043 (3)	0.046 (3)	0.031 (3)	0.002 (2)	0.008 (2)	0.005 (2)
O13	0.060 (2)	0.067 (2)	0.0362 (19)	0.0164 (18)	0.0133 (17)	0.0030 (18)
C111	0.056 (3)	0.062 (3)	0.043 (3)	0.007 (3)	0.016 (2)	0.007 (3)
C112	0.061 (3)	0.085 (4)	0.038 (3)	0.009 (3)	−0.012 (2)	−0.005 (3)

Geometric parameters (Å, º)

Br1—C2	1.871 (4)	C9—O9	1.209 (5)
S1—C2	1.720 (5)	C9—O10	1.349 (5)
S1—C5	1.725 (5)	O10—C11	1.448 (5)
C2—C3	1.330 (6)	C11—O12	1.427 (5)
C3—N4	1.382 (5)	C11—C111	1.506 (6)
C3—H3	0.9300	C11—C112	1.507 (6)
N4—C5	1.289 (5)	O12—C13	1.362 (5)
C5—N6	1.394 (5)	C13—O13	1.204 (5)
N6—C7	1.323 (5)	C111—H11A	0.9600
N6—H6	0.8675	C111—H11B	0.9600
C7—C8	1.368 (6)	C111—H11C	0.9600
C7—H7	0.9300	C112—H11D	0.9600
C8—C9	1.435 (6)	C112—H11E	0.9600
C8—C13	1.458 (6)	C112—H11F	0.9600
C2—S1—C5	87.7 (2)	C9—O10—C11	118.2 (3)
C3—C2—S1	111.7 (3)	O12—C11—O10	110.0 (3)
C3—C2—Br1	126.7 (4)	O12—C11—C111	111.0 (4)
S1—C2—Br1	121.6 (3)	O10—C11—C111	110.0 (4)
C2—C3—N4	114.5 (4)	O12—C11—C112	106.5 (4)
C2—C3—H3	122.8	O10—C11—C112	105.9 (4)
N4—C3—H3	122.8	C111—C11—C112	113.2 (4)
C5—N4—C3	110.6 (4)	C13—O12—C11	118.0 (3)
N4—C5—N6	122.1 (4)	O13—C13—O12	118.2 (4)
N4—C5—S1	115.6 (3)	O13—C13—C8	126.1 (4)
N6—C5—S1	122.3 (3)	O12—C13—C8	115.6 (4)
C7—N6—C5	120.9 (4)	C11—C111—H11A	109.5
C7—N6—H6	121.6	C11—C111—H11B	109.5
C5—N6—H6	117.3	H11A—C111—H11B	109.5
N6—C7—C8	127.8 (4)	C11—C111—H11C	109.5
N6—C7—H7	116.1	H11A—C111—H11C	109.5
C8—C7—H7	116.1	H11B—C111—H11C	109.5
C7—C8—C9	122.5 (4)	C11—C112—H11D	109.5
C7—C8—C13	116.8 (4)	C11—C112—H11E	109.5
C9—C8—C13	120.5 (4)	H11D—C112—H11E	109.5
O9—C9—O10	118.9 (4)	C11—C112—H11F	109.5
O9—C9—C8	124.6 (4)	H11D—C112—H11F	109.5
O10—C9—C8	116.4 (4)	H11E—C112—H11F	109.5
C5—S1—C2—C3	−0.2 (4)	C7—C8—C9—O10	−175.1 (4)
C5—S1—C2—Br1	−178.8 (3)	C13—C8—C9—O10	10.4 (6)
S1—C2—C3—N4	−0.2 (5)	O9—C9—O10—C11	−161.7 (4)
Br1—C2—C3—N4	178.3 (3)	C8—C9—O10—C11	20.1 (6)
C2—C3—N4—C5	0.6 (6)	C9—O10—C11—O12	−49.4 (5)
C3—N4—C5—N6	−179.1 (4)	C9—O10—C11—C111	73.2 (5)
C3—N4—C5—S1	−0.8 (5)	C9—O10—C11—C112	−164.1 (4)
C2—S1—C5—N4	0.6 (4)	O10—C11—O12—C13	50.1 (5)
C2—S1—C5—N6	178.9 (4)	C111—C11—O12—C13	−71.9 (5)
N4—C5—N6—C7	5.4 (6)	C112—C11—O12—C13	164.5 (4)
S1—C5—N6—C7	−172.8 (3)	C11—O12—C13—O13	161.1 (4)
C5—N6—C7—C8	176.5 (4)	C11—O12—C13—C8	−22.0 (6)
N6—C7—C8—C9	1.1 (7)	C7—C8—C13—O13	−7.8 (7)
N6—C7—C8—C13	175.8 (4)	C9—C8—C13—O13	167.0 (4)
C7—C8—C9—O9	6.8 (7)	C7—C8—C13—O12	175.6 (4)
C13—C8—C9—O9	−167.7 (4)	C9—C8—C13—O12	−9.6 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O9	0.87	2.24	2.798 (5)	122
N6—H6···O9^i	0.87	2.18	2.996 (5)	156

Symmetry code: (i) −x, −y, −z.