4,6-Dihy-droxy-4,6-dimethyl-1,3-diazinane-2-thione.

In the title compound, C(6)H(12)N(2)O(2)S, the heterocyclic ring has a sofa conformation. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯O hydrogen-bond inter-action with graph-set motif S(6). In the crystal, mol-ecules are linked by O-H⋯S, N-H⋯S and N-H⋯O hydrogen-bond inter-actions, forming an extended two-dimensional framework parallel to the ac plane.

Related literature

For the preparation of pyrimidines by reactions of 1,3-dicarbonyl compounds (e.g. ethyl acetoacetate, acetyl­acetone) with urea, thio­urea, guanidine, see: Barton & Ollis (1979 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C6H12N2O2S

M = 176.24

Triclinic,

a = 5.2425 (4) Å

b = 8.7047 (6) Å

c = 9.4370 (7) Å

α = 74.812 (1)°

β = 88.670 (1)°

γ = 79.708 (1)°

V = 408.80 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.903, T max = 0.934

4260 measured reflections

1760 independent reflections

1557 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.080

S = 1.00

1760 reflections

102 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681103145X/bt5602sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103145X/bt5602Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103145X/bt5602Isup3.cml

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

C6H12N2O2S	Z = 2
Mr = 176.24	F(000) = 188
Triclinic, P1	Dx = 1.432 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2425 (4) Å	Cell parameters from 2799 reflections
b = 8.7047 (6) Å	θ = 2.2–28.4°
c = 9.4370 (7) Å	µ = 0.35 mm−1
α = 74.812 (1)°	T = 296 K
β = 88.670 (1)°	Needle, colourless
γ = 79.708 (1)°	0.30 × 0.20 × 0.20 mm
V = 408.80 (5) Å3

Bruker APEXII CCD diffractometer	1760 independent reflections
Radiation source: fine-focus sealed tube	1557 reflections with I > 2σ(I)
graphite	Rint = 0.012
φ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −6→6
Tmin = 0.903, Tmax = 0.934	k = −11→11
4260 measured reflections	l = −12→12

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)] = 0.029	Hydrogen site location: difference Fourier map
wR(F2) = 0.080	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0543P)2 + 0.0583P] where P = (Fo2 + 2Fc2)/3
1760 reflections	(Δ/σ)max = 0.001
102 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.17 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
O1	−0.13693 (17)	0.81379 (12)	0.96252 (10)	0.0356 (2)
H1O	−0.2022	0.8234	0.8749	0.053*
O2	−0.14367 (17)	0.74017 (12)	0.69909 (10)	0.0366 (2)
H2O	−0.1954	0.7791	0.6065	0.055*
N1	0.2210 (2)	0.86785 (12)	0.64127 (11)	0.0280 (2)
H1N	0.2746	0.8901	0.5457	0.034*
N2	0.2262 (2)	0.92771 (12)	0.86480 (11)	0.0279 (2)
H2N	0.2349	1.0033	0.9160	0.033*
S1	0.35950 (7)	1.14664 (4)	0.63906 (3)	0.03452 (13)
C1	0.2615 (2)	0.96882 (14)	0.72002 (13)	0.0244 (2)
C2	0.1320 (2)	0.71395 (14)	0.70201 (13)	0.0273 (3)
C3	0.2177 (2)	0.65313 (14)	0.86236 (13)	0.0285 (3)
H3A	0.4050	0.6213	0.8688	0.034*
H3B	0.1433	0.5581	0.9075	0.034*
C4	0.1366 (2)	0.78007 (15)	0.94675 (13)	0.0269 (3)
C5	0.2428 (3)	0.59777 (17)	0.61166 (16)	0.0391 (3)
H5A	0.1869	0.6437	0.5109	0.059*
H5B	0.1827	0.4971	0.6486	0.059*
H5C	0.4287	0.5790	0.6183	0.059*
C6	0.2540 (3)	0.72820 (18)	1.10103 (14)	0.0365 (3)
H6A	0.1999	0.8124	1.1494	0.055*
H6B	0.4397	0.7081	1.0962	0.055*
H6C	0.1966	0.6312	1.1551	0.055*

	U11	U22	U33	U12	U13	U23
O1	0.0260 (4)	0.0510 (6)	0.0316 (5)	−0.0065 (4)	0.0043 (4)	−0.0147 (4)
O2	0.0294 (5)	0.0502 (6)	0.0331 (5)	−0.0117 (4)	−0.0005 (4)	−0.0128 (4)
N1	0.0366 (5)	0.0270 (5)	0.0231 (5)	−0.0107 (4)	0.0039 (4)	−0.0081 (4)
N2	0.0347 (5)	0.0276 (5)	0.0236 (5)	−0.0084 (4)	0.0025 (4)	−0.0091 (4)
S1	0.0502 (2)	0.02887 (19)	0.02849 (18)	−0.01687 (14)	0.00523 (14)	−0.00838 (13)
C1	0.0229 (5)	0.0250 (6)	0.0256 (6)	−0.0036 (4)	0.0006 (4)	−0.0076 (4)
C2	0.0294 (6)	0.0256 (6)	0.0296 (6)	−0.0077 (5)	0.0026 (5)	−0.0104 (5)
C3	0.0303 (6)	0.0249 (6)	0.0293 (6)	−0.0059 (5)	0.0021 (5)	−0.0048 (5)
C4	0.0252 (6)	0.0309 (6)	0.0242 (6)	−0.0048 (4)	0.0018 (4)	−0.0067 (5)
C5	0.0509 (8)	0.0324 (7)	0.0400 (7)	−0.0099 (6)	0.0072 (6)	−0.0188 (6)
C6	0.0388 (7)	0.0420 (7)	0.0256 (6)	−0.0044 (6)	−0.0037 (5)	−0.0050 (5)

O1—C4	1.4237 (14)	C2—C5	1.5185 (17)
O1—H1O	0.8800	C3—C4	1.5211 (17)
O2—C2	1.4223 (15)	C3—H3A	0.9700
O2—H2O	0.8800	C3—H3B	0.9700
N1—C1	1.3365 (15)	C4—C6	1.5166 (17)
N1—C2	1.4660 (15)	C5—H5A	0.9600
N1—H1N	0.9200	C5—H5B	0.9600
N2—C1	1.3359 (15)	C5—H5C	0.9600
N2—C4	1.4658 (15)	C6—H6A	0.9600
N2—H2N	0.9199	C6—H6B	0.9600
S1—C1	1.7001 (12)	C6—H6C	0.9600
C2—C3	1.5161 (17)
C4—O1—H1O	104.7	C4—C3—H3B	109.1
C2—O2—H2O	107.2	H3A—C3—H3B	107.9
C1—N1—C2	124.46 (10)	O1—C4—N2	109.54 (10)
C1—N1—H1N	117.0	O1—C4—C6	106.20 (10)
C2—N1—H1N	118.0	N2—C4—C6	109.09 (10)
C1—N2—C4	125.07 (10)	O1—C4—C3	112.36 (10)
C1—N2—H2N	118.2	N2—C4—C3	107.21 (9)
C4—N2—H2N	116.1	C6—C4—C3	112.39 (10)
N2—C1—N1	119.07 (11)	C2—C5—H5A	109.5
N2—C1—S1	119.89 (9)	C2—C5—H5B	109.5
N1—C1—S1	121.04 (9)	H5A—C5—H5B	109.5
O2—C2—N1	109.74 (10)	C2—C5—H5C	109.5
O2—C2—C3	106.53 (10)	H5A—C5—H5C	109.5
N1—C2—C3	107.89 (9)	H5B—C5—H5C	109.5
O2—C2—C5	111.08 (10)	C4—C6—H6A	109.5
N1—C2—C5	108.47 (10)	C4—C6—H6B	109.5
C3—C2—C5	113.05 (11)	H6A—C6—H6B	109.5
C2—C3—C4	112.40 (10)	C4—C6—H6C	109.5
C2—C3—H3A	109.1	H6A—C6—H6C	109.5
C4—C3—H3A	109.1	H6B—C6—H6C	109.5
C2—C3—H3B	109.1
C4—N2—C1—N1	−2.11 (17)	N1—C2—C3—C4	52.12 (13)
C4—N2—C1—S1	178.50 (8)	C5—C2—C3—C4	172.06 (10)
C2—N1—C1—N2	1.77 (18)	C1—N2—C4—O1	−94.88 (13)
C2—N1—C1—S1	−178.85 (9)	C1—N2—C4—C6	149.26 (11)
C1—N1—C2—O2	88.79 (13)	C1—N2—C4—C3	27.30 (15)
C1—N1—C2—C3	−26.90 (16)	C2—C3—C4—O1	68.34 (13)
C1—N1—C2—C5	−149.69 (12)	C2—C3—C4—N2	−52.07 (12)
O2—C2—C3—C4	−65.66 (12)	C2—C3—C4—C6	−171.94 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.88	1.98	2.727 (2)	143
O2—H2O···S1i	0.88	2.37	3.249 (1)	173
N1—H1N···S1ii	0.92	2.60	3.414 (1)	149
N2—H2N···O1iii	0.92	2.18	3.074 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2	0.88	1.98	2.727 (2)	143
O2—H2O⋯S1i	0.88	2.37	3.249 (1)	173
N1—H1N⋯S1ii	0.92	2.60	3.414 (1)	149
N2—H2N⋯O1iii	0.92	2.18	3.074 (2)	164

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