2-[6-Thioxo-5-(2,4,6-trimethyl-phen-yl)-1,3,5-thia-diazinan-3-yl]acetic acid.

In the mol-ecule of the title compound, C(14)H(18)N(2)O(2)S(2), the 1,3,5-thia-diazinane-2-thione ring adopts an envelope conformation with one of the N atoms at the flap position. The plane throught the five co-planar atoms of the heterocycle is oriented at a dihedral angle of 80.59 (8)° with respect to the aromatic ring. In the crystal structure, weak inter-molecular O-H⋯S inter-actions link the mol-ecules into chains along the b axis.

Related literature

For related structures, see: Arfan et al. (2009 ▶); Perez et al. (2001 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H18N2O2S2

M = 310.42

Orthorhombic,

a = 6.9134 (4) Å

b = 17.6934 (11) Å

c = 24.9073 (15) Å

V = 3046.7 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.35 mm−1

T = 296 K

0.26 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.922, T max = 0.942

18229 measured reflections

3957 independent reflections

2120 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.132

S = 1.03

3957 reflections

186 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011027/hk2650sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011027/hk2650Isup2.hkl

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

C14H18N2O2S2	F(000) = 1312
Mr = 310.42	Dx = 1.354 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3957 reflections
a = 6.9134 (4) Å	θ = 2.4–28.8°
b = 17.6934 (11) Å	µ = 0.35 mm−1
c = 24.9073 (15) Å	T = 296 K
V = 3046.7 (3) Å3	Prism, colorless
Z = 8	0.26 × 0.18 × 0.16 mm

Bruker Kappa APEXII CCD area-detector diffractometer	3957 independent reflections
Radiation source: fine-focus sealed tube	2120 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 7.40 pixels mm-1	θmax = 28.8°, θmin = 2.4°
ω scans	h = −9→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −24→21
Tmin = 0.922, Tmax = 0.942	l = −32→33
18229 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0418P)2 + 2.0698P] where P = (Fo2 + 2Fc2)/3
3957 reflections	(Δ/σ)max = 0.001
186 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.05204 (10)	0.04895 (4)	0.06455 (3)	0.0462 (3)
S2	−0.05342 (10)	0.17988 (4)	0.12532 (3)	0.0502 (3)
O1	0.4812 (3)	−0.14565 (11)	0.15003 (8)	0.0521 (7)
O2	0.5343 (4)	−0.12709 (11)	0.06276 (9)	0.0639 (9)
N1	0.3157 (3)	0.14751 (11)	0.10199 (8)	0.0342 (7)
N2	0.4407 (3)	0.02387 (12)	0.07081 (9)	0.0409 (8)
C1	0.3789 (4)	0.21613 (14)	0.12872 (11)	0.0355 (8)
C2	0.4250 (4)	0.27902 (14)	0.09806 (11)	0.0382 (9)
C3	0.4943 (4)	0.34268 (15)	0.12500 (13)	0.0465 (10)
C4	0.5158 (4)	0.34412 (16)	0.18049 (13)	0.0494 (10)
C5	0.4705 (4)	0.27966 (16)	0.20908 (13)	0.0508 (11)
C6	0.4040 (4)	0.21442 (15)	0.18430 (12)	0.0423 (9)
C7	0.3984 (5)	0.28082 (17)	0.03821 (12)	0.0554 (11)
C8	0.5854 (5)	0.41477 (18)	0.20860 (15)	0.0693 (14)
C9	0.3599 (5)	0.14439 (18)	0.21674 (12)	0.0617 (11)
C10	0.1280 (4)	0.13078 (13)	0.09810 (10)	0.0356 (8)
C11	0.2787 (4)	0.01152 (15)	0.03629 (12)	0.0455 (10)
C12	0.4777 (4)	0.10269 (14)	0.07749 (13)	0.0451 (10)
C13	0.4446 (4)	−0.02219 (15)	0.11916 (11)	0.0465 (10)
C14	0.4921 (4)	−0.10347 (15)	0.10630 (13)	0.0444 (10)
H1	0.49414	−0.19027	0.14189	0.0625*
H3	0.52712	0.38540	0.10524	0.0556*
H5	0.48496	0.27999	0.24620	0.0610*
H7A	0.43567	0.32952	0.02473	0.0833*
H7B	0.47751	0.24253	0.02198	0.0833*
H7C	0.26508	0.27157	0.02968	0.0833*
H8A	0.62761	0.45096	0.18238	0.1037*
H8B	0.48151	0.43591	0.22931	0.1037*
H8C	0.69113	0.40233	0.23195	0.1037*
H9A	0.35779	0.15697	0.25423	0.0926*
H9B	0.23599	0.12472	0.20634	0.0926*
H9C	0.45771	0.10699	0.21028	0.0926*
H11A	0.30305	0.03556	0.00195	0.0545*
H11B	0.26428	−0.04230	0.03002	0.0545*
H12A	0.59162	0.10850	0.09985	0.0542*
H12B	0.50755	0.12413	0.04261	0.0542*
H13A	0.54067	−0.00223	0.14376	0.0558*
H13B	0.31956	−0.01976	0.13673	0.0558*

	U11	U22	U33	U12	U13	U23
S1	0.0368 (4)	0.0420 (4)	0.0599 (5)	−0.0050 (3)	−0.0129 (4)	−0.0075 (3)
S2	0.0299 (4)	0.0516 (4)	0.0691 (5)	−0.0026 (3)	0.0024 (4)	−0.0111 (4)
O1	0.0600 (14)	0.0462 (11)	0.0501 (13)	0.0040 (10)	−0.0039 (10)	−0.0002 (10)
O2	0.0921 (18)	0.0482 (12)	0.0515 (14)	0.0146 (12)	0.0067 (12)	−0.0035 (10)
N1	0.0269 (12)	0.0358 (11)	0.0400 (12)	−0.0034 (9)	−0.0015 (10)	−0.0034 (10)
N2	0.0376 (13)	0.0370 (11)	0.0480 (15)	−0.0003 (10)	−0.0085 (11)	−0.0055 (10)
C1	0.0239 (13)	0.0399 (13)	0.0428 (16)	−0.0024 (11)	−0.0024 (12)	−0.0071 (12)
C2	0.0284 (14)	0.0413 (14)	0.0449 (17)	−0.0015 (11)	0.0032 (13)	−0.0034 (12)
C3	0.0335 (15)	0.0419 (15)	0.064 (2)	−0.0063 (12)	0.0084 (14)	−0.0060 (14)
C4	0.0315 (16)	0.0516 (17)	0.065 (2)	−0.0068 (13)	0.0022 (14)	−0.0210 (15)
C5	0.0442 (19)	0.0621 (19)	0.0462 (18)	−0.0059 (15)	−0.0053 (14)	−0.0130 (15)
C6	0.0360 (16)	0.0484 (15)	0.0424 (17)	−0.0044 (12)	−0.0028 (13)	−0.0027 (13)
C7	0.067 (2)	0.0509 (17)	0.0483 (19)	0.0009 (15)	0.0060 (16)	0.0016 (14)
C8	0.057 (2)	0.067 (2)	0.084 (3)	−0.0187 (17)	0.0041 (19)	−0.0321 (19)
C9	0.075 (2)	0.068 (2)	0.0420 (19)	−0.0127 (18)	−0.0066 (17)	0.0043 (16)
C10	0.0345 (15)	0.0360 (13)	0.0364 (15)	−0.0026 (11)	−0.0045 (12)	0.0027 (11)
C11	0.0473 (18)	0.0419 (15)	0.0472 (18)	0.0015 (13)	−0.0078 (14)	−0.0055 (13)
C12	0.0338 (16)	0.0385 (14)	0.063 (2)	0.0005 (12)	0.0006 (14)	−0.0089 (13)
C13	0.0435 (17)	0.0489 (15)	0.0472 (18)	0.0094 (14)	−0.0111 (14)	−0.0064 (13)
C14	0.0398 (17)	0.0446 (15)	0.0488 (19)	0.0032 (12)	−0.0093 (14)	−0.0020 (14)

S1—C10	1.752 (2)	C6—C9	1.510 (4)
S1—C11	1.841 (3)	C13—C14	1.510 (4)
S2—C10	1.670 (3)	C3—H3	0.9300
O1—C14	1.323 (4)	C5—H5	0.9300
O2—C14	1.198 (4)	C7—H7A	0.9600
O1—H1	0.8200	C7—H7B	0.9600
N1—C1	1.452 (3)	C7—H7C	0.9600
N1—C12	1.502 (3)	C8—H8A	0.9600
N1—C10	1.335 (3)	C8—H8B	0.9600
N2—C12	1.428 (3)	C8—H8C	0.9600
N2—C13	1.454 (3)	C9—H9A	0.9600
N2—C11	1.429 (4)	C9—H9B	0.9600
C1—C6	1.396 (4)	C9—H9C	0.9600
C1—C2	1.387 (4)	C11—H11A	0.9700
C2—C3	1.396 (4)	C11—H11B	0.9700
C2—C7	1.502 (4)	C12—H12A	0.9700
C3—C4	1.390 (5)	C12—H12B	0.9700
C4—C5	1.381 (4)	C13—H13A	0.9700
C4—C8	1.511 (4)	C13—H13B	0.9700
C5—C6	1.387 (4)
S1···C11i	3.561 (3)	C14···C3iv	3.526 (4)
S1···S1i	3.7226 (11)	C14···C2iv	3.561 (4)
S2···O1ii	3.187 (2)	C1···H1ii	3.0800
S2···C6	3.540 (3)	C7···H12B	2.8800
S1···H7Aiii	3.2000	C10···H9B	2.8000
S1···H3iv	3.1100	C12···H7B	2.8300
S1···H13B	2.8500	C14···H11B	2.6900
S2···H12Av	2.8300	H1···S2iv	2.3700
S2···H9Avi	3.0900	H1···C1iv	3.0800
S2···H9B	3.0000	H3···H7A	2.3200
S2···H1ii	2.3700	H3···H8A	2.3500
O1···C3iv	3.352 (3)	H3···S1ii	3.1100
O1···S2iv	3.187 (2)	H5···H9A	2.3600
O1···C2iv	3.367 (3)	H5···O1ix	2.9100
O2···N2	2.756 (3)	H7A···H3	2.3200
O2···C11	3.094 (4)	H7A···S1x	3.2000
O1···H5vii	2.9100	H7B···N1	2.8400
O2···H11B	2.5300	H7B···C12	2.8300
O2···H11Aviii	2.5500	H7B···H12B	2.1700
O2···H12Bviii	2.6400	H7B···H7Cx	2.3800
O2···H7Civ	2.8600	H7C···N1	2.8600
N2···O2	2.756 (3)	H7C···H7Biii	2.3800
N2···C11viii	3.357 (4)	H7C···O2ii	2.8600
N1···H9B	2.6900	H8A···H3	2.3500
N1···H7B	2.8400	H8B···H8Cvi	2.3100
N1···H7C	2.8600	H8C···H8Bxi	2.3100
N2···H11Aviii	2.7400	H9A···H5	2.3600
C2···O1ii	3.367 (3)	H9A···S2xi	3.0900
C2···C14ii	3.561 (4)	H9B···S2	3.0000
C3···O1ii	3.352 (3)	H9B···N1	2.6900
C3···C14ii	3.526 (4)	H9B···C10	2.8000
C6···S2	3.540 (3)	H11A···H12B	2.3400
C7···C12	3.345 (4)	H11A···O2viii	2.5500
C7···C10	3.573 (4)	H11A···N2viii	2.7400
C9···C10	3.371 (4)	H11B···O2	2.5300
C10···C7	3.573 (4)	H11B···C14	2.6900
C10···C9	3.371 (4)	H12A···S2xii	2.8300
C10···C13	3.520 (4)	H12A···H13A	2.2700
C11···S1i	3.561 (3)	H12B···C7	2.8800
C11···O2	3.094 (4)	H12B···H7B	2.1700
C11···N2viii	3.357 (4)	H12B···H11A	2.3400
C11···C11viii	3.577 (4)	H12B···O2viii	2.6400
C12···C7	3.345 (4)	H13A···H12A	2.2700
C13···C10	3.520 (4)	H13B···S1	2.8500
C10—S1—C11	102.97 (13)	C6—C5—H5	119.00
C14—O1—H1	109.00	C2—C7—H7A	109.00
C1—N1—C12	113.8 (2)	C2—C7—H7B	109.00
C10—N1—C12	125.4 (2)	C2—C7—H7C	109.00
C1—N1—C10	120.8 (2)	H7A—C7—H7B	109.00
C11—N2—C12	111.1 (2)	H7A—C7—H7C	109.00
C12—N2—C13	116.6 (2)	H7B—C7—H7C	109.00
C11—N2—C13	115.3 (2)	C4—C8—H8A	109.00
N1—C1—C2	119.2 (2)	C4—C8—H8B	109.00
C2—C1—C6	122.4 (2)	C4—C8—H8C	109.00
N1—C1—C6	118.3 (2)	H8A—C8—H8B	109.00
C1—C2—C3	117.5 (3)	H8A—C8—H8C	109.00
C1—C2—C7	122.4 (2)	H8B—C8—H8C	109.00
C3—C2—C7	120.1 (2)	C6—C9—H9A	109.00
C2—C3—C4	122.0 (3)	C6—C9—H9B	109.00
C3—C4—C5	118.3 (3)	C6—C9—H9C	109.00
C5—C4—C8	121.1 (3)	H9A—C9—H9B	109.00
C3—C4—C8	120.6 (3)	H9A—C9—H9C	109.00
C4—C5—C6	122.2 (3)	H9B—C9—H9C	109.00
C1—C6—C5	117.7 (3)	S1—C11—H11A	109.00
C1—C6—C9	121.6 (2)	S1—C11—H11B	109.00
C5—C6—C9	120.8 (3)	N2—C11—H11A	109.00
S1—C10—S2	113.48 (16)	N2—C11—H11B	109.00
S1—C10—N1	120.62 (19)	H11A—C11—H11B	108.00
S2—C10—N1	125.84 (19)	N1—C12—H12A	108.00
S1—C11—N2	112.5 (2)	N1—C12—H12B	108.00
N1—C12—N2	115.4 (2)	N2—C12—H12A	108.00
N2—C13—C14	111.2 (2)	N2—C12—H12B	108.00
O1—C14—C13	110.5 (2)	H12A—C12—H12B	107.00
O2—C14—C13	125.3 (3)	N2—C13—H13A	109.00
O1—C14—O2	124.2 (2)	N2—C13—H13B	109.00
C2—C3—H3	119.00	C14—C13—H13A	109.00
C4—C3—H3	119.00	C14—C13—H13B	109.00
C4—C5—H5	119.00	H13A—C13—H13B	108.00
C11—S1—C10—S2	176.80 (15)	N1—C1—C2—C3	−176.9 (2)
C11—S1—C10—N1	−5.7 (2)	N1—C1—C2—C7	4.5 (4)
C10—S1—C11—N2	35.4 (2)	C6—C1—C2—C3	−1.6 (4)
C10—N1—C1—C2	−98.6 (3)	C6—C1—C2—C7	179.9 (3)
C10—N1—C1—C6	85.9 (3)	N1—C1—C6—C5	177.9 (2)
C12—N1—C1—C2	77.9 (3)	N1—C1—C6—C9	−2.3 (4)
C12—N1—C1—C6	−97.7 (3)	C2—C1—C6—C5	2.6 (4)
C1—N1—C10—S1	178.62 (18)	C2—C1—C6—C9	−177.7 (3)
C1—N1—C10—S2	−4.3 (3)	C1—C2—C3—C4	−0.5 (4)
C12—N1—C10—S1	2.6 (3)	C7—C2—C3—C4	178.1 (3)
C12—N1—C10—S2	179.7 (2)	C2—C3—C4—C5	1.4 (4)
C1—N1—C12—N2	155.3 (2)	C2—C3—C4—C8	−178.1 (3)
C10—N1—C12—N2	−28.4 (4)	C3—C4—C5—C6	−0.3 (4)
C12—N2—C11—S1	−63.8 (3)	C8—C4—C5—C6	179.2 (3)
C13—N2—C11—S1	71.7 (2)	C4—C5—C6—C1	−1.6 (4)
C11—N2—C12—N1	60.6 (3)	C4—C5—C6—C9	178.7 (3)
C13—N2—C12—N1	−74.3 (3)	N2—C13—C14—O1	−175.4 (2)
C11—N2—C13—C14	72.2 (3)	N2—C13—C14—O2	4.7 (4)
C12—N2—C13—C14	−154.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S2iv	0.82	2.37	3.187 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯S2i	0.82	2.37	3.187 (2)	174

Symmetry code: (i) .