2-[N-(2,4-Dimeth-oxy-phen-yl)acetamido]-1,3-thia-zol-4-yl acetate.

The title compound, C15H16N2O5S, is a product of the reaction of 2-(2,4-dimeth-oxy-phenyl-amino)-1,3-thia-zol-4(5H)-one with acetic anhydride. The presence of the acetyl and acet-oxy groups in the mol-ecule indicates that the starting thia-zole exists as a tautomer in the reaction mixture with exocyclic amino and enol moieties. The acetyl group is tilted slightly from the heterocyclic ring plane [dihedral angle = 4.46 (11)°], while the acet-oxy group is almost perpendicular to this ring [dihedral angle = 88.14 (12)°]. An intra-molecular acet-yl-meth-oxy C-H⋯O inter-action is noted. In the crystal, mol-ecules are connected into a three-dimensional architecture by C-H⋯O inter-actions.

Related literature

For the biological activity of 2-aryl­amino­thia­zol-4-one derivatives, see: Chen et al. (2007 ▶); Eriksson et al. (2007 ▶); Lesyk & Zimenkovsky (2004 ▶); Lesyk et al. (2011 ▶); Ottana et al. (2005 ▶); Subtelna et al. (2010 ▶); Vassilev et al. (2006 ▶). For prototropic tautomerism studies, see: Subtelna et al. (2010 ▶); Lesyk et al. (2003 ▶); Vana et al. (2009 ▶).

Experimental

Crystal data

C15H16N2O5S

M = 336.36

Triclinic,

a = 9.1486 (11) Å

b = 9.3592 (13) Å

c = 10.2823 (8) Å

α = 69.212 (10)°

β = 82.910 (8)°

γ = 77.220 (11)°

V = 801.73 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 130 K

0.30 × 0.30 × 0.10 mm

Data collection

Agilent Xcalibur Atlas diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.919, T max = 1.000

10576 measured reflections

3822 independent reflections

3281 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.06

3822 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813003474/tk5194sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003474/tk5194Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003474/tk5194Isup3.cml

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

C15H16N2O5S	Z = 2
Mr = 336.36	F(000) = 352
Triclinic, P1	Dx = 1.393 Mg m−3
Hall symbol: -P 1	Melting point = 391–393 K
a = 9.1486 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3592 (13) Å	Cell parameters from 4534 reflections
c = 10.2823 (8) Å	θ = 2.1–29.0°
α = 69.212 (10)°	µ = 0.23 mm−1
β = 82.910 (8)°	T = 130 K
γ = 77.220 (11)°	Plate, light-orange
V = 801.73 (16) Å3	0.30 × 0.30 × 0.10 mm

Agilent Xcalibur Atlas diffractometer	3822 independent reflections
Radiation source: fine-focus sealed tube	3281 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 10.3088 pixels mm-1	θmax = 29.1°, θmin = 2.1°
ω scans	h = −11→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→11
Tmin = 0.919, Tmax = 1.000	l = −13→13
10576 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.2365P] where P = (Fo2 + 2Fc2)/3
3822 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.32458 (4)	0.43206 (4)	0.29160 (4)	0.02952 (11)
C2	0.31474 (13)	0.61823 (14)	0.16952 (13)	0.0216 (3)
N3	0.32110 (12)	0.72722 (12)	0.21915 (11)	0.0230 (2)
C4	0.33664 (14)	0.66136 (16)	0.35971 (14)	0.0263 (3)
C5	0.34049 (15)	0.50714 (17)	0.41887 (15)	0.0310 (3)
H5	0.3502	0.4503	0.5132	0.037*
N6	0.29963 (12)	0.65332 (12)	0.02702 (11)	0.0216 (2)
C7	0.30067 (14)	0.53574 (15)	−0.02554 (15)	0.0260 (3)
O8	0.31721 (12)	0.40055 (11)	0.05240 (12)	0.0346 (2)
C9	0.28173 (17)	0.58190 (17)	−0.17857 (16)	0.0319 (3)
H9A	0.1797	0.6325	−0.1990	0.048*
H9B	0.3057	0.4908	−0.2054	0.048*
H9C	0.3477	0.6521	−0.2293	0.048*
C10	0.27699 (14)	0.81557 (14)	−0.05890 (12)	0.0194 (2)
C11	0.13373 (14)	0.89309 (14)	−0.10249 (12)	0.0190 (2)
C12	0.10876 (14)	1.05180 (14)	−0.18041 (12)	0.0195 (2)
H12	0.0137	1.1044	−0.2108	0.023*
C13	0.22900 (14)	1.13041 (14)	−0.21197 (12)	0.0197 (2)
C14	0.37236 (14)	1.05301 (15)	−0.17013 (13)	0.0215 (3)
H14	0.4517	1.1063	−0.1933	0.026*
C15	0.39576 (14)	0.89529 (14)	−0.09341 (13)	0.0212 (3)
H15	0.4914	0.8424	−0.0648	0.025*
O16	0.02463 (10)	0.80501 (10)	−0.06499 (9)	0.0232 (2)
C17	−0.11652 (15)	0.87342 (16)	−0.12963 (15)	0.0286 (3)
H17A	−0.1002	0.9041	−0.2290	0.043*
H17B	−0.1623	0.9632	−0.1043	0.043*
H17C	−0.1814	0.7988	−0.0988	0.043*
O18	0.21456 (10)	1.28646 (10)	−0.28607 (9)	0.0248 (2)
C19	0.06590 (15)	1.37616 (15)	−0.31019 (16)	0.0302 (3)
H19A	0.0173	1.3412	−0.3677	0.045*
H19B	0.0707	1.4841	−0.3562	0.045*
H19C	0.0099	1.3634	−0.2228	0.045*
O20	0.35830 (11)	0.76068 (12)	0.42650 (10)	0.0312 (2)
C21	0.23193 (17)	0.84306 (18)	0.47107 (14)	0.0322 (3)
O22	0.11015 (12)	0.81482 (15)	0.47434 (13)	0.0452 (3)
C23	0.2701 (2)	0.9684 (2)	0.51145 (18)	0.0450 (4)
H23A	0.3330	0.9221	0.5896	0.067*
H23B	0.1796	1.0297	0.5362	0.067*
H23C	0.3223	1.0338	0.4344	0.067*

	U11	U22	U33	U12	U13	U23
S1	0.02693 (19)	0.01603 (17)	0.0364 (2)	−0.00475 (13)	−0.00359 (14)	0.00326 (14)
C2	0.0166 (6)	0.0141 (6)	0.0289 (6)	−0.0034 (4)	−0.0025 (5)	−0.0002 (5)
N3	0.0214 (5)	0.0197 (5)	0.0247 (5)	−0.0049 (4)	−0.0030 (4)	−0.0024 (4)
C4	0.0199 (6)	0.0288 (7)	0.0260 (6)	−0.0061 (5)	−0.0036 (5)	−0.0027 (5)
C5	0.0248 (7)	0.0315 (7)	0.0273 (7)	−0.0073 (6)	−0.0039 (5)	0.0033 (6)
N6	0.0226 (5)	0.0127 (5)	0.0274 (5)	−0.0042 (4)	−0.0026 (4)	−0.0034 (4)
C7	0.0198 (6)	0.0190 (6)	0.0405 (8)	−0.0052 (5)	0.0000 (5)	−0.0113 (6)
O8	0.0358 (6)	0.0157 (5)	0.0515 (7)	−0.0058 (4)	−0.0038 (5)	−0.0094 (4)
C9	0.0333 (8)	0.0275 (7)	0.0409 (8)	−0.0067 (6)	−0.0005 (6)	−0.0187 (6)
C10	0.0245 (6)	0.0127 (5)	0.0204 (6)	−0.0049 (5)	−0.0016 (5)	−0.0038 (5)
C11	0.0206 (6)	0.0179 (6)	0.0200 (6)	−0.0075 (5)	0.0002 (4)	−0.0062 (5)
C12	0.0198 (6)	0.0175 (6)	0.0200 (6)	−0.0041 (4)	−0.0019 (4)	−0.0044 (5)
C13	0.0261 (6)	0.0151 (6)	0.0174 (5)	−0.0064 (5)	0.0000 (5)	−0.0036 (5)
C14	0.0217 (6)	0.0196 (6)	0.0240 (6)	−0.0091 (5)	0.0004 (5)	−0.0059 (5)
C15	0.0196 (6)	0.0194 (6)	0.0243 (6)	−0.0038 (5)	−0.0023 (5)	−0.0065 (5)
O16	0.0211 (4)	0.0170 (4)	0.0303 (5)	−0.0082 (3)	−0.0020 (4)	−0.0035 (4)
C17	0.0240 (7)	0.0261 (7)	0.0361 (7)	−0.0109 (5)	−0.0056 (5)	−0.0061 (6)
O18	0.0244 (5)	0.0154 (4)	0.0291 (5)	−0.0067 (3)	−0.0030 (4)	0.0017 (4)
C19	0.0272 (7)	0.0177 (6)	0.0388 (8)	−0.0046 (5)	−0.0097 (6)	0.0015 (6)
O20	0.0287 (5)	0.0387 (6)	0.0271 (5)	−0.0107 (4)	−0.0029 (4)	−0.0092 (4)
C21	0.0339 (8)	0.0385 (8)	0.0226 (6)	−0.0085 (6)	−0.0043 (5)	−0.0066 (6)
O22	0.0312 (6)	0.0562 (8)	0.0564 (7)	−0.0090 (5)	−0.0007 (5)	−0.0290 (6)
C23	0.0506 (10)	0.0543 (11)	0.0388 (9)	−0.0167 (8)	−0.0028 (7)	−0.0222 (8)

S1—C5	1.7240 (16)	C12—H12	0.9300
S1—C2	1.7394 (13)	C13—O18	1.3714 (14)
C2—N3	1.3067 (17)	C13—C14	1.3884 (18)
C2—N6	1.4008 (17)	C14—C15	1.3865 (17)
N3—C4	1.3669 (17)	C14—H14	0.9300
C4—C5	1.347 (2)	C15—H15	0.9300
C4—O20	1.3941 (17)	O16—C17	1.4364 (16)
C5—H5	0.9300	C17—H17A	0.9600
N6—C7	1.3855 (17)	C17—H17B	0.9600
N6—C10	1.4433 (15)	C17—H17C	0.9600
C7—O8	1.2212 (16)	O18—C19	1.4305 (16)
C7—C9	1.498 (2)	C19—H19A	0.9600
C9—H9A	0.9600	C19—H19B	0.9600
C9—H9B	0.9600	C19—H19C	0.9600
C9—H9C	0.9600	O20—C21	1.3663 (18)
C10—C11	1.3923 (17)	C21—O22	1.1945 (18)
C10—C15	1.3924 (17)	C21—C23	1.494 (2)
C11—O16	1.3667 (14)	C23—H23A	0.9600
C11—C12	1.3967 (17)	C23—H23B	0.9600
C12—C13	1.3989 (17)	C23—H23C	0.9600
C5—S1—C2	88.67 (7)	O18—C13—C12	123.00 (11)
N3—C2—N6	120.83 (11)	C14—C13—C12	121.30 (11)
N3—C2—S1	115.54 (10)	C15—C14—C13	119.16 (11)
N6—C2—S1	123.63 (10)	C15—C14—H14	120.4
C2—N3—C4	108.68 (11)	C13—C14—H14	120.4
C5—C4—N3	118.10 (13)	C14—C15—C10	120.40 (11)
C5—C4—O20	126.10 (12)	C14—C15—H15	119.8
N3—C4—O20	115.62 (12)	C10—C15—H15	119.8
C4—C5—S1	109.00 (10)	C11—O16—C17	117.33 (10)
C4—C5—H5	125.5	O16—C17—H17A	109.5
S1—C5—H5	125.5	O16—C17—H17B	109.5
C7—N6—C2	120.34 (11)	H17A—C17—H17B	109.5
C7—N6—C10	122.54 (11)	O16—C17—H17C	109.5
C2—N6—C10	117.07 (10)	H17A—C17—H17C	109.5
O8—C7—N6	119.83 (13)	H17B—C17—H17C	109.5
O8—C7—C9	122.69 (12)	C13—O18—C19	117.54 (10)
N6—C7—C9	117.48 (12)	O18—C19—H19A	109.5
C7—C9—H9A	109.5	O18—C19—H19B	109.5
C7—C9—H9B	109.5	H19A—C19—H19B	109.5
H9A—C9—H9B	109.5	O18—C19—H19C	109.5
C7—C9—H9C	109.5	H19A—C19—H19C	109.5
H9A—C9—H9C	109.5	H19B—C19—H19C	109.5
H9B—C9—H9C	109.5	C21—O20—C4	116.53 (11)
C11—C10—C15	120.31 (11)	O22—C21—O20	122.45 (14)
C11—C10—N6	119.22 (10)	O22—C21—C23	127.05 (15)
C15—C10—N6	120.42 (11)	O20—C21—C23	110.50 (13)
O16—C11—C10	116.17 (10)	C21—C23—H23A	109.5
O16—C11—C12	123.96 (11)	C21—C23—H23B	109.5
C10—C11—C12	119.87 (11)	H23A—C23—H23B	109.5
C11—C12—C13	118.95 (11)	C21—C23—H23C	109.5
C11—C12—H12	120.5	H23A—C23—H23C	109.5
C13—C12—H12	120.5	H23B—C23—H23C	109.5
O18—C13—C14	115.70 (10)
C5—S1—C2—N3	−0.65 (10)	C15—C10—C11—O16	179.31 (11)
C5—S1—C2—N6	179.91 (11)	N6—C10—C11—O16	−3.12 (17)
N6—C2—N3—C4	−179.64 (11)	C15—C10—C11—C12	−0.44 (18)
S1—C2—N3—C4	0.91 (14)	N6—C10—C11—C12	177.13 (11)
C2—N3—C4—C5	−0.79 (17)	O16—C11—C12—C13	179.61 (11)
C2—N3—C4—O20	174.60 (11)	C10—C11—C12—C13	−0.66 (18)
N3—C4—C5—S1	0.31 (16)	C11—C12—C13—O18	−179.03 (11)
O20—C4—C5—S1	−174.54 (11)	C11—C12—C13—C14	1.49 (18)
C2—S1—C5—C4	0.17 (10)	O18—C13—C14—C15	179.30 (11)
N3—C2—N6—C7	176.71 (11)	C12—C13—C14—C15	−1.19 (19)
S1—C2—N6—C7	−3.88 (17)	C13—C14—C15—C10	0.06 (18)
N3—C2—N6—C10	−5.82 (17)	C11—C10—C15—C14	0.75 (18)
S1—C2—N6—C10	173.58 (9)	N6—C10—C15—C14	−176.78 (11)
C2—N6—C7—O8	−1.16 (19)	C10—C11—O16—C17	−168.59 (11)
C10—N6—C7—O8	−178.48 (11)	C12—C11—O16—C17	11.15 (17)
C2—N6—C7—C9	179.13 (11)	C14—C13—O18—C19	−169.30 (11)
C10—N6—C7—C9	1.80 (18)	C12—C13—O18—C19	11.20 (17)
C7—N6—C10—C11	74.41 (16)	C5—C4—O20—C21	−97.28 (16)
C2—N6—C10—C11	−102.99 (13)	N3—C4—O20—C21	87.75 (14)
C7—N6—C10—C15	−108.02 (14)	C4—O20—C21—O22	12.0 (2)
C2—N6—C10—C15	74.57 (15)	C4—O20—C21—C23	−167.56 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O16	0.96	2.57	3.1838 (19)	122
C5—H5···O18i	0.93	2.47	3.2465 (18)	141
C15—H15···O8ii	0.93	2.52	3.3117 (18)	143
C17—H17C···O8iii	0.96	2.35	3.2945 (19)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O16	0.96	2.57	3.1838 (19)	122
C5—H5⋯O18i	0.93	2.47	3.2465 (18)	141
C15—H15⋯O8ii	0.93	2.52	3.3117 (18)	143
C17—H17C⋯O8iii	0.96	2.35	3.2945 (19)	170

Symmetry codes: (i) ; (ii) ; (iii) .