1-(2-Chloro-1,3-thia-zol-5-ylmeth-yl)-3,5-dimethyl-2-nitrimino-1,2,3,4,5,6-hexa-hydro-1,3,5-triazine.

In the title compound, C(9)H(13)ClN(6)O(2)S, all bond lengths and angles are normal. The 1,3,5-triazine ring exhibits a half-chair conformation. In the crystal structure, weak inter-molecular C-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the bc plane.

Related literature

For synthesis of the title compound, see: Frank et al. (1990 ▶). For related crystal structures, see: Zurn et al. (1982 ▶). For useful applications of related compounds, see: Motohiro (2000 ▶).

Experimental

Crystal data

C9H13ClN6O2S

M = 304.76

Monoclinic,

a = 32.864 (7) Å

b = 6.4063 (13) Å

c = 13.569 (3) Å

β = 110.53 (3)°

V = 2675.3 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.45 mm−1

T = 293 (2) K

0.32 × 0.22 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi 1995 ▶) T min = 0.869, T max = 0.956

9419 measured reflections

2363 independent reflections

1985 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.145

S = 1.17

2363 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.33 e Å−3

Data collection: RAPID-AUTO (Rigaku 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2001 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062071/cv2360sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062071/cv2360Isup2.hkl

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

C9H13ClN6O2S	F000 = 1264
Mr = 304.76	Dx = 1.513 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2652 reflections
a = 32.864 (7) Å	θ = 2.6–25.6º
b = 6.4063 (13) Å	µ = 0.45 mm−1
c = 13.569 (3) Å	T = 293 (2) K
β = 110.53 (3)º	Block, colourless
V = 2675.3 (11) Å3	0.32 × 0.22 × 0.10 mm
Z = 8

Rigaku R-AXIS RAPID IP area-detector diffractometer	2363 independent reflections
Radiation source: Rotating Anode	1985 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 153(2) K	θmax = 25.0º
ω Oscillation scans	θmin = 3.0º
Absorption correction: multi-scan(ABSCOR; Higashi 1995)	h = −38→38
Tmin = 0.869, Tmax = 0.956	k = −7→7
9419 measured reflections	l = −16→14

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0788P)2 + 1.7911P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.145	(Δ/σ)max < 0.001
S = 1.17	Δρmax = 0.38 e Å−3
2363 reflections	Δρmin = −0.33 e Å−3
173 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0107 (11)
Secondary atom site location: difference Fourier map

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	0.06171 (2)	0.27878 (12)	0.16669 (7)	0.0561 (3)
Cl1	−0.03042 (2)	0.41507 (14)	0.09448 (8)	0.0715 (3)
C1	0.00747 (8)	0.2188 (4)	0.1269 (2)	0.0456 (6)
N1	−0.00266 (8)	0.0260 (4)	0.1214 (2)	0.0551 (6)
O1	0.15917 (9)	0.4743 (4)	0.2334 (2)	0.0874 (9)
N2	0.14362 (6)	−0.0081 (3)	0.15051 (14)	0.0355 (5)
C2	0.03521 (9)	−0.0889 (5)	0.1509 (2)	0.0541 (7)
H2A	0.0346	−0.2340	0.1520	0.065*
O2	0.19505 (9)	0.4278 (4)	0.40121 (19)	0.0825 (8)
N3	0.14082 (7)	0.0518 (3)	−0.02674 (15)	0.0415 (5)
C3	0.07300 (8)	0.0158 (4)	0.17781 (18)	0.0378 (6)
N4	0.20026 (6)	0.1676 (3)	0.12543 (16)	0.0403 (5)
C4	0.11820 (8)	−0.0718 (4)	0.21546 (19)	0.0408 (6)
H4A	0.1332	−0.0265	0.2873	0.049*
H4B	0.1165	−0.2230	0.2157	0.049*
N5	0.19224 (7)	0.1754 (3)	0.29169 (16)	0.0456 (6)
C5	0.13045 (9)	−0.0922 (4)	0.04226 (19)	0.0470 (7)
H5B	0.1452	−0.2236	0.0432	0.056*
H5C	0.0994	−0.1189	0.0160	0.056*
C6	0.17769 (7)	0.1185 (4)	0.18622 (17)	0.0333 (5)
N6	0.18187 (8)	0.3633 (4)	0.30871 (19)	0.0527 (6)
C7	0.18655 (8)	0.0946 (4)	0.01513 (19)	0.0454 (6)
H7A	0.1935	0.2005	−0.0275	0.054*
H7B	0.2025	−0.0311	0.0118	0.054*
C8	0.11418 (10)	0.2411 (5)	−0.0471 (2)	0.0559 (8)
H8A	0.1225	0.3313	−0.0932	0.084*
H8B	0.1184	0.3120	0.0181	0.084*
H8C	0.0841	0.2041	−0.0795	0.084*
C9	0.23765 (9)	0.3080 (5)	0.1597 (3)	0.0594 (8)
H9A	0.2435	0.3482	0.2315	0.089*
H9B	0.2315	0.4301	0.1159	0.089*
H9C	0.2626	0.2380	0.1541	0.089*

	U11	U22	U33	U12	U13	U23
S1	0.0366 (4)	0.0366 (4)	0.0967 (6)	−0.0027 (3)	0.0252 (4)	−0.0049 (3)
Cl1	0.0430 (4)	0.0628 (6)	0.1085 (7)	0.0110 (3)	0.0262 (4)	0.0014 (4)
C1	0.0374 (13)	0.0489 (16)	0.0538 (15)	−0.0002 (12)	0.0200 (12)	−0.0001 (12)
N1	0.0405 (12)	0.0520 (15)	0.0704 (15)	−0.0082 (11)	0.0165 (11)	0.0040 (12)
O1	0.105 (2)	0.0537 (14)	0.0933 (18)	0.0394 (15)	0.0215 (16)	−0.0055 (13)
N2	0.0382 (11)	0.0361 (11)	0.0352 (10)	−0.0033 (9)	0.0167 (8)	−0.0010 (8)
C2	0.0520 (17)	0.0361 (15)	0.0735 (18)	−0.0093 (12)	0.0211 (14)	0.0036 (13)
O2	0.1016 (19)	0.0792 (18)	0.0685 (14)	−0.0091 (14)	0.0320 (13)	−0.0434 (13)
N3	0.0451 (12)	0.0470 (13)	0.0362 (10)	−0.0016 (10)	0.0188 (9)	−0.0025 (9)
C3	0.0409 (13)	0.0387 (14)	0.0375 (12)	−0.0007 (11)	0.0183 (10)	0.0041 (10)
N4	0.0339 (10)	0.0429 (12)	0.0461 (11)	−0.0048 (9)	0.0165 (9)	−0.0043 (9)
C4	0.0444 (14)	0.0400 (14)	0.0426 (13)	0.0043 (11)	0.0209 (11)	0.0103 (11)
N5	0.0539 (14)	0.0410 (12)	0.0371 (11)	0.0073 (10)	0.0098 (10)	−0.0071 (9)
C5	0.0559 (16)	0.0464 (16)	0.0426 (13)	−0.0155 (13)	0.0223 (12)	−0.0121 (11)
C6	0.0331 (12)	0.0303 (12)	0.0352 (11)	0.0089 (10)	0.0104 (9)	0.0018 (9)
N6	0.0506 (13)	0.0488 (14)	0.0603 (14)	0.0043 (12)	0.0213 (11)	−0.0158 (12)
C7	0.0460 (14)	0.0533 (16)	0.0440 (13)	−0.0004 (12)	0.0247 (11)	−0.0040 (11)
C8	0.0573 (18)	0.067 (2)	0.0438 (14)	0.0142 (15)	0.0177 (13)	0.0042 (13)
C9	0.0440 (15)	0.064 (2)	0.0733 (19)	−0.0178 (14)	0.0239 (14)	−0.0106 (15)

S1—C1	1.715 (3)	N4—C9	1.461 (3)
S1—C3	1.720 (3)	N4—C7	1.479 (3)
Cl1—C1	1.715 (3)	C4—H4A	0.9700
C1—N1	1.275 (4)	C4—H4B	0.9700
N1—C2	1.379 (4)	N5—N6	1.294 (3)
O1—N6	1.254 (3)	N5—C6	1.389 (3)
N2—C6	1.329 (3)	C5—H5B	0.9700
N2—C4	1.469 (3)	C5—H5C	0.9700
N2—C5	1.480 (3)	C7—H7A	0.9700
C2—C3	1.344 (4)	C7—H7B	0.9700
C2—H2A	0.9300	C8—H8A	0.9600
O2—N6	1.246 (3)	C8—H8B	0.9600
N3—C7	1.434 (3)	C8—H8C	0.9600
N3—C5	1.438 (3)	C9—H9A	0.9600
N3—C8	1.464 (3)	C9—H9B	0.9600
C3—C4	1.500 (3)	C9—H9C	0.9600
N4—C6	1.326 (3)
C1—S1—C3	88.66 (13)	N2—C5—H5B	109.4
N1—C1—Cl1	123.0 (2)	N3—C5—H5C	109.4
N1—C1—S1	117.2 (2)	N2—C5—H5C	109.4
Cl1—C1—S1	119.85 (17)	H5B—C5—H5C	108.0
C1—N1—C2	108.0 (2)	N4—C6—N2	120.1 (2)
C6—N2—C4	122.32 (19)	N4—C6—N5	120.9 (2)
C6—N2—C5	120.00 (19)	N2—C6—N5	118.5 (2)
C4—N2—C5	117.67 (19)	O2—N6—O1	122.0 (3)
C3—C2—N1	117.8 (3)	O2—N6—N5	117.9 (3)
C3—C2—H2A	121.1	O1—N6—N5	120.1 (2)
N1—C2—H2A	121.1	N3—C7—N4	111.47 (19)
C7—N3—C5	108.6 (2)	N3—C7—H7A	109.3
C7—N3—C8	113.0 (2)	N4—C7—H7A	109.3
C5—N3—C8	113.1 (2)	N3—C7—H7B	109.3
C2—C3—C4	128.0 (3)	N4—C7—H7B	109.3
C2—C3—S1	108.3 (2)	H7A—C7—H7B	108.0
C4—C3—S1	123.62 (19)	N3—C8—H8A	109.5
C6—N4—C9	122.7 (2)	N3—C8—H8B	109.5
C6—N4—C7	121.1 (2)	H8A—C8—H8B	109.5
C9—N4—C7	116.1 (2)	N3—C8—H8C	109.5
N2—C4—C3	113.29 (19)	H8A—C8—H8C	109.5
N2—C4—H4A	108.9	H8B—C8—H8C	109.5
C3—C4—H4A	108.9	N4—C9—H9A	109.5
N2—C4—H4B	108.9	N4—C9—H9B	109.5
C3—C4—H4B	108.9	H9A—C9—H9B	109.5
H4A—C4—H4B	107.7	N4—C9—H9C	109.5
N6—N5—C6	114.3 (2)	H9A—C9—H9C	109.5
N3—C5—N2	111.0 (2)	H9B—C9—H9C	109.5
N3—C5—H5B	109.4
C3—S1—C1—N1	0.1 (2)	C9—N4—C6—N2	179.1 (2)
C3—S1—C1—Cl1	−178.89 (18)	C7—N4—C6—N2	4.0 (3)
Cl1—C1—N1—C2	178.9 (2)	C9—N4—C6—N5	−9.2 (4)
S1—C1—N1—C2	−0.1 (3)	C7—N4—C6—N5	175.6 (2)
C1—N1—C2—C3	0.0 (4)	C4—N2—C6—N4	178.4 (2)
N1—C2—C3—C4	178.0 (2)	C5—N2—C6—N4	−0.8 (3)
N1—C2—C3—S1	0.1 (3)	C4—N2—C6—N5	6.5 (3)
C1—S1—C3—C2	−0.1 (2)	C5—N2—C6—N5	−172.7 (2)
C1—S1—C3—C4	−178.1 (2)	N6—N5—C6—N4	84.1 (3)
C6—N2—C4—C3	112.1 (3)	N6—N5—C6—N2	−104.1 (3)
C5—N2—C4—C3	−68.7 (3)	C6—N5—N6—O2	−177.7 (2)
C2—C3—C4—N2	123.3 (3)	C6—N5—N6—O1	2.4 (4)
S1—C3—C4—N2	−59.1 (3)	C5—N3—C7—N4	−54.3 (3)
C7—N3—C5—N2	57.2 (3)	C8—N3—C7—N4	72.1 (3)
C8—N3—C5—N2	−69.0 (3)	C6—N4—C7—N3	24.6 (3)
C6—N2—C5—N3	−30.6 (3)	C9—N4—C7—N3	−150.9 (2)
C4—N2—C5—N3	150.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···N3i	0.97	2.45	3.314 (3)	148
C4—H4B···O1ii	0.97	2.36	3.178 (3)	142
C7—H7A···O2iii	0.97	2.58	3.483 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯N3i	0.97	2.45	3.314 (3)	148
C4—H4B⋯O1ii	0.97	2.36	3.178 (3)	142
C7—H7A⋯O2iii	0.97	2.58	3.483 (4)	156

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