(Z)-2-[(2,4-Dimethyl-phen-yl)imino]-1,3-thia-zinan-4-one.

In the title compound, C(12)H(14)N(2)OS, the 1,3-thia-zinane ring displays a screw-boat conformation. In the crystal, pairs of centrosymmetrically related mol-ecules are linked by pairs of N-H⋯O hydrogen bonds into dimers. C-H⋯π inter-actions occur between adjacent dimers.

Related literature

For pharmaceutical applications of 4-thia­zinones, see: Mogilaiah et al. (1999 ▶); Turkevich et al., 1977) ▶. For the synthesis, see: Mansuroğlu et al. (2009 ▶); Schroth et al. (1977 ▶).

Experimental

Crystal data

C12H14N2OS

M = 234.31

Triclinic,

a = 7.2325 (4) Å

b = 9.2000 (7) Å

c = 10.0513 (7) Å

α = 114.184 (7)°

β = 94.647 (5)°

γ = 97.910 (5)°

V = 597.27 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.48 × 0.28 × 0.23 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2008 ▶) T min = 0.919, T max = 0.944

4061 measured reflections

2188 independent reflections

1569 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.115

S = 1.06

2188 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2008 ▶); 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051147/xu5100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051147/xu5100Isup2.hkl

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

C12H14N2OS	Z = 2
Mr = 234.31	F(000) = 248
Triclinic, P1	Dx = 1.303 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2325 (4) Å	Cell parameters from 1436 reflections
b = 9.2000 (7) Å	θ = 2.8–29.2°
c = 10.0513 (7) Å	µ = 0.25 mm−1
α = 114.184 (7)°	T = 293 K
β = 94.647 (5)°	Block, colorless
γ = 97.910 (5)°	0.48 × 0.28 × 0.23 mm
V = 597.27 (7) Å3

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	2188 independent reflections
Radiation source: fine-focus sealed tube	1569 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 10.3592 pixels mm-1	θmax = 25.4°, θmin = 2.9°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2008)	k = −10→11
Tmin = 0.919, Tmax = 0.944	l = −12→9
4061 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0414P)2 + 0.175P] where P = (Fo2 + 2Fc2)/3
2188 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.28 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	0.55185 (9)	0.52363 (7)	0.33010 (8)	0.0523 (3)
O1	0.8076 (2)	1.03840 (19)	0.5892 (2)	0.0549 (5)
N1	0.9131 (3)	0.5481 (2)	0.2917 (2)	0.0440 (5)
N2	0.8280 (3)	0.7918 (2)	0.4195 (2)	0.0421 (5)
H2	0.9236	0.8376	0.3961	0.051*
C1	0.7441 (4)	−0.1475 (3)	0.0075 (4)	0.0823 (11)
H1A	0.6145	−0.1836	−0.0386	0.123*
H1B	0.7650	−0.1892	0.0797	0.123*
H1C	0.8247	−0.1863	−0.0658	0.123*
C2	0.7884 (3)	0.0354 (3)	0.0820 (3)	0.0518 (7)
C3	0.8622 (4)	0.1187 (3)	0.2294 (3)	0.0580 (8)
H3	0.8850	0.0615	0.2848	0.070*
C4	0.9027 (4)	0.2862 (3)	0.2960 (3)	0.0501 (7)
H4	0.9552	0.3403	0.3952	0.060*
C5	0.8663 (3)	0.3743 (3)	0.2171 (3)	0.0399 (6)
C6	0.7938 (3)	0.2946 (3)	0.0679 (3)	0.0445 (6)
C7	0.7569 (3)	0.1258 (3)	0.0048 (3)	0.0540 (8)
H7	0.7082	0.0710	−0.0951	0.065*
C8	0.7535 (4)	0.3858 (4)	−0.0223 (3)	0.0680 (9)
H8B	0.7962	0.3363	−0.1158	0.102*
H8C	0.8184	0.4964	0.0293	0.102*
H8A	0.6201	0.3829	−0.0379	0.102*
C9	0.7833 (3)	0.6224 (3)	0.3455 (3)	0.0360 (6)
C10	0.4370 (3)	0.6924 (3)	0.4178 (3)	0.0544 (7)
H10B	0.4074	0.7384	0.3491	0.065*
H10A	0.3191	0.6545	0.4433	0.065*
C11	0.5592 (3)	0.8223 (3)	0.5554 (3)	0.0477 (7)
H11B	0.4893	0.9078	0.6024	0.057*
H11A	0.5883	0.7760	0.6239	0.057*
C12	0.7393 (3)	0.8938 (3)	0.5241 (3)	0.0399 (6)

	U11	U22	U33	U12	U13	U23
S1	0.0440 (4)	0.0327 (4)	0.0669 (5)	0.0023 (3)	0.0113 (3)	0.0090 (3)
O1	0.0525 (11)	0.0270 (9)	0.0719 (13)	0.0066 (8)	0.0125 (9)	0.0076 (9)
N1	0.0416 (12)	0.0317 (11)	0.0496 (13)	0.0072 (9)	0.0078 (10)	0.0080 (10)
N2	0.0430 (12)	0.0269 (10)	0.0518 (13)	0.0043 (8)	0.0119 (10)	0.0122 (10)
C1	0.0548 (19)	0.0368 (16)	0.125 (3)	0.0045 (14)	0.0134 (19)	0.0060 (18)
C2	0.0361 (14)	0.0315 (14)	0.071 (2)	0.0091 (11)	0.0085 (13)	0.0047 (14)
C3	0.0553 (17)	0.0445 (16)	0.076 (2)	0.0150 (13)	0.0086 (15)	0.0258 (16)
C4	0.0546 (16)	0.0413 (15)	0.0446 (16)	0.0119 (12)	0.0002 (12)	0.0094 (13)
C5	0.0353 (13)	0.0336 (13)	0.0439 (15)	0.0107 (10)	0.0076 (11)	0.0081 (12)
C6	0.0384 (14)	0.0434 (15)	0.0439 (16)	0.0091 (11)	0.0055 (11)	0.0108 (13)
C7	0.0403 (15)	0.0465 (16)	0.0502 (17)	0.0053 (12)	0.0024 (12)	−0.0023 (14)
C8	0.075 (2)	0.075 (2)	0.0517 (19)	0.0139 (17)	0.0047 (15)	0.0268 (17)
C9	0.0401 (13)	0.0299 (12)	0.0344 (13)	0.0056 (10)	0.0024 (10)	0.0110 (11)
C10	0.0406 (15)	0.0461 (15)	0.0656 (19)	0.0094 (12)	0.0104 (13)	0.0123 (14)
C11	0.0487 (15)	0.0364 (14)	0.0521 (17)	0.0107 (11)	0.0135 (12)	0.0112 (13)
C12	0.0425 (14)	0.0312 (13)	0.0440 (15)	0.0101 (11)	0.0042 (11)	0.0133 (12)

S1—C9	1.754 (2)	C4—C5	1.381 (4)
S1—C10	1.798 (3)	C4—H4	0.9300
O1—C12	1.223 (3)	C5—C6	1.388 (3)
N1—C9	1.264 (3)	C6—C7	1.391 (3)
N1—C5	1.436 (3)	C6—C8	1.503 (4)
N2—C12	1.365 (3)	C7—H7	0.9300
N2—C9	1.400 (3)	C8—H8B	0.9600
N2—H2	0.8600	C8—H8C	0.9600
C1—C2	1.509 (3)	C8—H8A	0.9600
C1—H1A	0.9600	C10—C11	1.510 (3)
C1—H1B	0.9600	C10—H10B	0.9700
C1—H1C	0.9600	C10—H10A	0.9700
C2—C7	1.378 (4)	C11—C12	1.492 (3)
C2—C3	1.378 (4)	C11—H11B	0.9700
C3—C4	1.381 (3)	C11—H11A	0.9700
C3—H3	0.9300
C9—S1—C10	101.58 (11)	C2—C7—H7	118.2
C9—N1—C5	117.4 (2)	C6—C7—H7	118.2
C12—N2—C9	128.4 (2)	C6—C8—H8B	109.5
C12—N2—H2	115.8	C6—C8—H8C	109.5
C9—N2—H2	115.8	H8B—C8—H8C	109.5
C2—C1—H1A	109.5	C6—C8—H8A	109.5
C2—C1—H1B	109.5	H8B—C8—H8A	109.5
H1A—C1—H1B	109.5	H8C—C8—H8A	109.5
C2—C1—H1C	109.5	N1—C9—N2	117.8 (2)
H1A—C1—H1C	109.5	N1—C9—S1	123.15 (18)
H1B—C1—H1C	109.5	N2—C9—S1	119.04 (17)
C7—C2—C3	117.3 (2)	C11—C10—S1	111.74 (18)
C7—C2—C1	121.2 (3)	C11—C10—H10B	109.3
C3—C2—C1	121.5 (3)	S1—C10—H10B	109.3
C2—C3—C4	120.9 (3)	C11—C10—H10A	109.3
C2—C3—H3	119.6	S1—C10—H10A	109.3
C4—C3—H3	119.6	H10B—C10—H10A	107.9
C3—C4—C5	120.7 (3)	C12—C11—C10	112.6 (2)
C3—C4—H4	119.6	C12—C11—H11B	109.1
C5—C4—H4	119.6	C10—C11—H11B	109.1
C4—C5—C6	120.0 (2)	C12—C11—H11A	109.1
C4—C5—N1	118.3 (2)	C10—C11—H11A	109.1
C6—C5—N1	121.6 (2)	H11B—C11—H11A	107.8
C5—C6—C7	117.3 (3)	O1—C12—N2	120.2 (2)
C5—C6—C8	121.7 (2)	O1—C12—C11	122.0 (2)
C7—C6—C8	120.9 (2)	N2—C12—C11	117.8 (2)
C2—C7—C6	123.7 (3)
C7—C2—C3—C4	−0.1 (4)	C8—C6—C7—C2	−179.1 (2)
C1—C2—C3—C4	179.7 (3)	C5—N1—C9—N2	179.5 (2)
C2—C3—C4—C5	1.4 (4)	C5—N1—C9—S1	−1.1 (3)
C3—C4—C5—C6	−2.1 (4)	C12—N2—C9—N1	−156.8 (2)
C3—C4—C5—N1	−179.4 (2)	C12—N2—C9—S1	23.7 (3)
C9—N1—C5—C4	−94.8 (3)	C10—S1—C9—N1	−177.0 (2)
C9—N1—C5—C6	87.9 (3)	C10—S1—C9—N2	2.4 (2)
C4—C5—C6—C7	1.4 (4)	C9—S1—C10—C11	−41.6 (2)
N1—C5—C6—C7	178.6 (2)	S1—C10—C11—C12	62.2 (3)
C4—C5—C6—C8	−179.6 (2)	C9—N2—C12—O1	172.6 (2)
N1—C5—C6—C8	−2.4 (4)	C9—N2—C12—C11	−7.2 (4)
C3—C2—C7—C6	−0.6 (4)	C10—C11—C12—O1	141.7 (2)
C1—C2—C7—C6	179.6 (2)	C10—C11—C12—N2	−38.5 (3)
C5—C6—C7—C2	0.0 (4)

Cg2 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	2.08	2.900 (3)	161
C1—H1C···Cg2ii	0.96	2.72	3.591 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.08	2.900 (3)	161
C1—H1C⋯Cg2ii	0.96	2.72	3.591 (3)	152

Symmetry codes: (i) ; (ii) .