1-[(1,3-Dithio-lan-2-yl)meth-yl]-6-methyl-8-nitro-1,2,3,5,6,7-hexa-hydro-imidazo[1,2-c]pyrimidine.

In the title compound, C(11)H(18)N(4)O(2)S(2), the dithiol-ane ring displays an envelope conformation, the tetra-hydro-pyrimidine ring has a conformation that is between half-chair and screw-boat, and the imidazole ring is essentially planar (r.m.s. deviation = 0.0017 Å). No significant directional inter-molecular inter-actions are present in the structure.

Related literature

For related structures, see: Tian et al. (2009 ▶). For background to neonicotinoid insecticides, see Mori et al. (2001 ▶); Kagabu (1997 ▶); Tian et al. (2007 ▶).

Experimental

Crystal data

C11H18N4O2S2

M = 302.41

Triclinic,

a = 8.0326 (7) Å

b = 9.3521 (8) Å

c = 10.1109 (9) Å

α = 80.461 (1)°

β = 83.497 (1)°

γ = 68.043 (1)°

V = 693.62 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.39 mm−1

T = 293 K

0.26 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.906, T max = 0.934

7993 measured reflections

3178 independent reflections

2826 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.06

3178 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003206X/zl2297sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003206X/zl2297Isup2.hkl

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

C11H18N4O2S2	Z = 2
Mr = 302.41	F(000) = 320
Triclinic, P1	Dx = 1.448 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0326 (7) Å	Cell parameters from 4541 reflections
b = 9.3521 (8) Å	θ = 2.4–27.7°
c = 10.1109 (9) Å	µ = 0.39 mm−1
α = 80.461 (1)°	T = 293 K
β = 83.497 (1)°	Prism, colourless
γ = 68.043 (1)°	0.26 × 0.23 × 0.18 mm
V = 693.62 (10) Å3

Bruker APEXII CCD area-detector diffractometer	3178 independent reflections
Radiation source: fine-focus sealed tube	2826 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 27.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.906, Tmax = 0.934	k = −12→11
7993 measured reflections	l = −13→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0447P)2 + 0.2729P] where P = (Fo2 + 2Fc2)/3
3178 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.34 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
C1	0.92947 (18)	0.16249 (17)	0.65277 (14)	0.0319 (3)
C2	1.0078 (2)	0.10338 (19)	0.78875 (16)	0.0375 (3)
H2A	0.9189	0.1516	0.8570	0.045*
H2B	1.0364	−0.0081	0.8074	0.045*
C3	1.2634 (3)	0.0458 (2)	0.9163 (2)	0.0549 (5)
H3A	1.2903	−0.0628	0.9137	0.082*
H3B	1.1876	0.0770	0.9949	0.082*
H3C	1.3731	0.0636	0.9189	0.082*
C4	1.2876 (2)	0.0997 (2)	0.67697 (17)	0.0409 (4)
H4A	1.3993	0.1141	0.6851	0.049*
H4B	1.3154	−0.0077	0.6650	0.049*
C5	1.2874 (2)	0.2345 (2)	0.43686 (17)	0.0459 (4)
H5A	1.3595	0.1393	0.4003	0.055*
H5B	1.3635	0.2914	0.4466	0.055*
C6	1.1325 (2)	0.3324 (3)	0.35069 (19)	0.0544 (5)
H6A	1.1106	0.4422	0.3466	0.065*
H6B	1.1554	0.3050	0.2602	0.065*
C7	1.02457 (19)	0.22041 (17)	0.54533 (14)	0.0316 (3)
C8	0.7976 (2)	0.40401 (18)	0.38887 (15)	0.0361 (3)
H8A	0.8020	0.5074	0.3646	0.043*
H8B	0.7182	0.4057	0.4688	0.043*
C9	0.7185 (2)	0.36571 (18)	0.27473 (15)	0.0369 (3)
H9	0.7140	0.2614	0.3005	0.044*
C10	0.7343 (3)	0.5774 (2)	0.0715 (2)	0.0580 (5)
H10A	0.7905	0.6289	0.1179	0.070*
H10B	0.7517	0.6059	−0.0244	0.070*
C11	0.5376 (3)	0.6301 (2)	0.1105 (2)	0.0553 (5)
H11A	0.4723	0.6319	0.0349	0.066*
H11B	0.4967	0.7350	0.1334	0.066*
N1	0.78451 (16)	0.12503 (15)	0.63650 (13)	0.0351 (3)
N2	1.17052 (18)	0.13662 (16)	0.79623 (13)	0.0379 (3)
N3	1.19480 (17)	0.20279 (17)	0.56373 (13)	0.0392 (3)
N4	0.97815 (17)	0.29393 (16)	0.42032 (13)	0.0371 (3)
O1	0.71913 (17)	0.14805 (16)	0.52435 (12)	0.0489 (3)
O2	0.72085 (16)	0.06008 (15)	0.73842 (12)	0.0468 (3)
S1	0.83905 (6)	0.36969 (6)	0.11346 (4)	0.04884 (14)
S2	0.49010 (6)	0.50283 (6)	0.25217 (5)	0.05506 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0265 (6)	0.0378 (7)	0.0330 (7)	−0.0138 (6)	−0.0029 (5)	−0.0035 (6)
C2	0.0335 (7)	0.0431 (8)	0.0374 (8)	−0.0172 (6)	−0.0063 (6)	0.0011 (6)
C3	0.0567 (11)	0.0614 (11)	0.0527 (11)	−0.0299 (9)	−0.0264 (9)	0.0123 (8)
C4	0.0278 (7)	0.0460 (9)	0.0500 (9)	−0.0147 (6)	−0.0088 (6)	−0.0018 (7)
C5	0.0339 (8)	0.0632 (11)	0.0447 (9)	−0.0253 (8)	0.0054 (7)	−0.0052 (8)
C6	0.0422 (9)	0.0823 (13)	0.0432 (9)	−0.0350 (9)	−0.0002 (7)	0.0080 (9)
C7	0.0273 (6)	0.0357 (7)	0.0345 (7)	−0.0137 (6)	−0.0021 (5)	−0.0063 (6)
C8	0.0357 (7)	0.0391 (8)	0.0330 (7)	−0.0133 (6)	−0.0027 (6)	−0.0035 (6)
C9	0.0377 (8)	0.0389 (8)	0.0347 (7)	−0.0155 (6)	−0.0057 (6)	−0.0001 (6)
C10	0.0654 (12)	0.0611 (12)	0.0487 (10)	−0.0323 (10)	−0.0003 (9)	0.0097 (9)
C11	0.0624 (12)	0.0449 (10)	0.0529 (11)	−0.0161 (9)	−0.0072 (9)	0.0039 (8)
N1	0.0296 (6)	0.0421 (7)	0.0368 (6)	−0.0173 (5)	−0.0016 (5)	−0.0039 (5)
N2	0.0367 (7)	0.0424 (7)	0.0384 (7)	−0.0187 (6)	−0.0115 (5)	0.0009 (5)
N3	0.0281 (6)	0.0519 (8)	0.0399 (7)	−0.0200 (6)	−0.0026 (5)	0.0010 (6)
N4	0.0312 (6)	0.0487 (7)	0.0322 (6)	−0.0179 (6)	−0.0007 (5)	−0.0005 (5)
O1	0.0481 (7)	0.0701 (8)	0.0408 (6)	−0.0360 (6)	−0.0129 (5)	0.0011 (6)
O2	0.0402 (6)	0.0648 (8)	0.0420 (6)	−0.0314 (6)	0.0006 (5)	0.0030 (5)
S1	0.0490 (3)	0.0596 (3)	0.0356 (2)	−0.0154 (2)	−0.00023 (17)	−0.01182 (18)
S2	0.0342 (2)	0.0736 (3)	0.0498 (3)	−0.0182 (2)	−0.00542 (18)	0.0116 (2)

C1—N1	1.3686 (18)	C6—H6B	0.9700
C1—C7	1.408 (2)	C7—N3	1.3455 (18)
C1—C2	1.509 (2)	C7—N4	1.3552 (19)
C2—N2	1.4642 (19)	C8—N4	1.4640 (19)
C2—H2A	0.9700	C8—C9	1.529 (2)
C2—H2B	0.9700	C8—H8A	0.9700
C3—N2	1.463 (2)	C8—H8B	0.9700
C3—H3A	0.9600	C9—S1	1.8019 (16)
C3—H3B	0.9600	C9—S2	1.8169 (16)
C3—H3C	0.9600	C9—H9	0.9800
C4—N3	1.444 (2)	C10—C11	1.495 (3)
C4—N2	1.448 (2)	C10—S1	1.802 (2)
C4—H4A	0.9700	C10—H10A	0.9700
C4—H4B	0.9700	C10—H10B	0.9700
C5—N3	1.452 (2)	C11—S2	1.8068 (19)
C5—C6	1.508 (2)	C11—H11A	0.9700
C5—H5A	0.9700	C11—H11B	0.9700
C5—H5B	0.9700	N1—O1	1.2559 (17)
C6—N4	1.488 (2)	N1—O2	1.2641 (17)
C6—H6A	0.9700
N1—C1—C7	123.33 (13)	N4—C8—H8A	108.8
N1—C1—C2	114.77 (12)	C9—C8—H8A	108.8
C7—C1—C2	120.49 (12)	N4—C8—H8B	108.8
N2—C2—C1	112.09 (12)	C9—C8—H8B	108.8
N2—C2—H2A	109.2	H8A—C8—H8B	107.7
C1—C2—H2A	109.2	C8—C9—S1	115.71 (11)
N2—C2—H2B	109.2	C8—C9—S2	109.68 (11)
C1—C2—H2B	109.2	S1—C9—S2	106.91 (8)
H2A—C2—H2B	107.9	C8—C9—H9	108.1
N2—C3—H3A	109.5	S1—C9—H9	108.1
N2—C3—H3B	109.5	S2—C9—H9	108.1
H3A—C3—H3B	109.5	C11—C10—S1	110.59 (13)
N2—C3—H3C	109.5	C11—C10—H10A	109.5
H3A—C3—H3C	109.5	S1—C10—H10A	109.5
H3B—C3—H3C	109.5	C11—C10—H10B	109.5
N3—C4—N2	107.66 (13)	S1—C10—H10B	109.5
N3—C4—H4A	110.2	H10A—C10—H10B	108.1
N2—C4—H4A	110.2	C10—C11—S2	111.27 (13)
N3—C4—H4B	110.2	C10—C11—H11A	109.4
N2—C4—H4B	110.2	S2—C11—H11A	109.4
H4A—C4—H4B	108.5	C10—C11—H11B	109.4
N3—C5—C6	101.87 (13)	S2—C11—H11B	109.4
N3—C5—H5A	111.4	H11A—C11—H11B	108.0
C6—C5—H5A	111.4	O1—N1—O2	120.14 (12)
N3—C5—H5B	111.4	O1—N1—C1	122.24 (13)
C6—C5—H5B	111.4	O2—N1—C1	117.56 (12)
H5A—C5—H5B	109.3	C4—N2—C3	110.33 (14)
N4—C6—C5	103.53 (13)	C4—N2—C2	110.28 (12)
N4—C6—H6A	111.1	C3—N2—C2	109.41 (13)
C5—C6—H6A	111.1	C7—N3—C4	120.45 (13)
N4—C6—H6B	111.1	C7—N3—C5	110.88 (13)
C5—C6—H6B	111.1	C4—N3—C5	122.79 (13)
H6A—C6—H6B	109.0	C7—N4—C8	123.79 (12)
N3—C7—N4	110.27 (13)	C7—N4—C6	108.50 (12)
N3—C7—C1	117.58 (13)	C8—N4—C6	117.02 (13)
N4—C7—C1	132.15 (13)	C10—S1—C9	93.94 (8)
N4—C8—C9	113.81 (13)	C11—S2—C9	98.01 (8)
N1—C1—C2—N2	175.52 (13)	N4—C7—N3—C5	−13.07 (19)
C7—C1—C2—N2	8.6 (2)	C1—C7—N3—C5	166.80 (14)
N3—C5—C6—N4	−20.74 (19)	N2—C4—N3—C7	−49.50 (19)
N1—C1—C7—N3	−157.53 (14)	N2—C4—N3—C5	159.98 (14)
C2—C1—C7—N3	8.2 (2)	C6—C5—N3—C7	21.40 (19)
N1—C1—C7—N4	22.3 (3)	C6—C5—N3—C4	174.39 (16)
C2—C1—C7—N4	−171.97 (15)	N3—C7—N4—C8	−144.85 (14)
N4—C8—C9—S1	−62.50 (16)	C1—C7—N4—C8	35.3 (2)
N4—C8—C9—S2	176.50 (10)	N3—C7—N4—C6	−1.68 (19)
S1—C10—C11—S2	28.7 (2)	C1—C7—N4—C6	178.48 (17)
C7—C1—N1—O1	−4.1 (2)	C9—C8—N4—C7	−127.28 (15)
C2—C1—N1—O1	−170.58 (14)	C9—C8—N4—C6	92.38 (18)
C7—C1—N1—O2	173.30 (14)	C5—C6—N4—C7	14.7 (2)
C2—C1—N1—O2	6.8 (2)	C5—C6—N4—C8	160.67 (14)
N3—C4—N2—C3	−174.80 (13)	C11—C10—S1—C9	−42.36 (16)
N3—C4—N2—C2	64.22 (16)	C8—C9—S1—C10	−82.86 (13)
C1—C2—N2—C4	−44.99 (17)	S2—C9—S1—C10	39.62 (10)
C1—C2—N2—C3	−166.51 (14)	C10—C11—S2—C9	−0.91 (17)
N4—C7—N3—C4	−166.78 (14)	C8—C9—S2—C11	99.63 (12)
C1—C7—N3—C4	13.1 (2)	S1—C9—S2—C11	−26.54 (10)