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

In the title compound, C(13)H(22)N(4)O(2)S(2), the six-membered ring displays a half-chair conformation. The olefin amine unit is close to being coplanar with the imidazolidine ring (r.m.s. deviation = 0.059 Å). The dithiol-ane ring adopts a twisted conformation. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions.

Related literature

For related structures, see Tian et al. (2010 ▶); Li et al. (2010 ▶). For background to neonicotinoid insecticides, see Mori et al. (2001 ▶); Ohno et al. (2009 ▶); Jeschke et al. (2008 ▶); Kagabu (1997 ▶); Tian et al. (2007 ▶).

Experimental

Crystal data

C13H22N4O2S2

M = 330.47

Monoclinic,

a = 11.9680 (3) Å

b = 13.6304 (3) Å

c = 10.8866 (3) Å

β = 115.465 (3)°

V = 1603.38 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.45 × 0.41 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.917, T max = 1.0

13404 measured reflections

3256 independent reflections

2486 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.096

S = 1.04

3256 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.16 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/S1600536810033829/hb5612sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033829/hb5612Isup2.hkl

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

C13H22N4O2S2	F(000) = 704
Mr = 330.47	Dx = 1.369 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 7164 reflections
a = 11.9680 (3) Å	θ = 3.3–28.9°
b = 13.6304 (3) Å	µ = 0.34 mm−1
c = 10.8866 (3) Å	T = 293 K
β = 115.465 (3)°	Prism, colourless
V = 1603.38 (8) Å3	0.45 × 0.41 × 0.26 mm
Z = 4

Bruker APEXII CCD diffractometer	3256 independent reflections
Radiation source: fine-focus sealed tube	2486 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 16.0355 pixels mm-1	θmax = 26.4°, θmin = 3.5°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −17→17
Tmin = 0.917, Tmax = 1.0	l = −13→13
13404 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0605P)2] where P = (Fo2 + 2Fc2)/3
3256 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.16 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	0.21596 (14)	0.03042 (13)	0.24992 (18)	0.0490 (4)
H1A	0.1584	0.0170	0.1565	0.059*
H1B	0.1937	−0.0110	0.3083	0.059*
C2	0.30273 (15)	0.15638 (14)	0.41120 (18)	0.0527 (4)
H2A	0.2960	0.1151	0.4803	0.063*
H2B	0.2949	0.2242	0.4336	0.063*
C3	0.52500 (16)	0.21274 (12)	0.46180 (18)	0.0488 (4)
H3B	0.5517	0.2262	0.5578	0.059*
H3A	0.5015	0.2737	0.4112	0.059*
C4	0.62423 (15)	0.15974 (12)	0.43666 (18)	0.0489 (4)
H4A	0.6609	0.2028	0.3931	0.059*
H4B	0.6889	0.1360	0.5214	0.059*
C5	0.44343 (13)	0.07042 (11)	0.34006 (14)	0.0358 (3)
C6	0.34568 (13)	0.00437 (12)	0.26942 (15)	0.0392 (4)
C7	0.58540 (13)	0.05456 (12)	0.23001 (15)	0.0389 (4)
H7B	0.6083	0.1149	0.1993	0.047*
H7A	0.5103	0.0303	0.1563	0.047*
C8	0.68837 (13)	−0.02085 (12)	0.25948 (15)	0.0372 (3)
H8	0.6626	−0.0827	0.2855	0.045*
C9	0.88413 (18)	0.07980 (17)	0.2809 (2)	0.0653 (6)
H9A	0.8400	0.1417	0.2552	0.078*
H9B	0.9721	0.0936	0.3266	0.078*
C10	0.85620 (19)	0.01841 (19)	0.1568 (2)	0.0737 (6)
H10B	0.9206	−0.0304	0.1765	0.088*
H10A	0.8548	0.0597	0.0836	0.088*
C11	0.19972 (16)	0.19983 (15)	0.17239 (19)	0.0577 (5)
H11A	0.2578	0.1771	0.1382	0.069*
H11B	0.2256	0.2647	0.2106	0.069*
C12	0.07252 (19)	0.20656 (19)	0.0556 (2)	0.0789 (7)
H12B	0.0785	0.2407	−0.0195	0.095*
H12A	0.0422	0.1409	0.0250	0.095*
C13	−0.01760 (19)	0.25861 (18)	0.0930 (3)	0.0896 (8)
H13B	−0.0983	0.2561	0.0181	0.134*
H13C	0.0073	0.3258	0.1140	0.134*
H13A	−0.0200	0.2276	0.1709	0.134*
N1	0.55919 (10)	0.07677 (9)	0.34598 (13)	0.0372 (3)
N2	0.42417 (11)	0.14173 (10)	0.41168 (13)	0.0436 (3)
N3	0.20390 (12)	0.13306 (11)	0.28063 (14)	0.0472 (4)
N4	0.36386 (12)	−0.08788 (10)	0.23411 (14)	0.0439 (3)
O1	0.46924 (10)	−0.12073 (8)	0.25825 (12)	0.0487 (3)
O2	0.26936 (11)	−0.14243 (10)	0.17994 (15)	0.0678 (4)
S1	0.70823 (4)	−0.04188 (4)	0.10432 (4)	0.05415 (16)
S2	0.83629 (3)	0.01316 (4)	0.39184 (4)	0.04712 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0408 (9)	0.0547 (11)	0.0542 (11)	0.0003 (8)	0.0230 (8)	0.0050 (8)
C2	0.0557 (10)	0.0621 (11)	0.0483 (10)	0.0097 (9)	0.0299 (8)	0.0015 (9)
C3	0.0617 (10)	0.0354 (8)	0.0463 (9)	−0.0014 (8)	0.0205 (8)	−0.0012 (8)
C4	0.0462 (9)	0.0384 (9)	0.0531 (10)	−0.0057 (7)	0.0128 (8)	−0.0025 (8)
C5	0.0377 (8)	0.0368 (8)	0.0319 (7)	0.0036 (6)	0.0140 (6)	0.0059 (6)
C6	0.0372 (8)	0.0417 (9)	0.0399 (8)	−0.0011 (7)	0.0177 (7)	−0.0014 (7)
C7	0.0335 (8)	0.0478 (9)	0.0336 (8)	0.0014 (7)	0.0128 (6)	0.0087 (7)
C8	0.0336 (7)	0.0456 (9)	0.0331 (7)	−0.0021 (7)	0.0150 (6)	0.0033 (7)
C9	0.0534 (11)	0.0806 (14)	0.0620 (12)	−0.0236 (10)	0.0249 (9)	−0.0013 (11)
C10	0.0649 (13)	0.1042 (17)	0.0659 (13)	−0.0218 (12)	0.0414 (11)	−0.0039 (12)
C11	0.0521 (10)	0.0646 (12)	0.0598 (11)	0.0118 (9)	0.0273 (9)	0.0205 (10)
C12	0.0761 (14)	0.0835 (16)	0.0628 (13)	0.0131 (12)	0.0162 (11)	0.0208 (12)
C13	0.0573 (12)	0.0760 (16)	0.122 (2)	0.0094 (11)	0.0252 (13)	0.0350 (15)
N1	0.0340 (6)	0.0366 (7)	0.0393 (7)	−0.0021 (5)	0.0143 (5)	−0.0013 (6)
N2	0.0453 (7)	0.0432 (8)	0.0427 (8)	0.0025 (6)	0.0194 (6)	−0.0047 (6)
N3	0.0445 (7)	0.0536 (9)	0.0483 (8)	0.0105 (6)	0.0246 (6)	0.0094 (7)
N4	0.0429 (7)	0.0457 (8)	0.0447 (8)	−0.0073 (6)	0.0203 (6)	−0.0049 (6)
O1	0.0441 (6)	0.0443 (6)	0.0623 (8)	−0.0003 (5)	0.0273 (5)	−0.0079 (6)
O2	0.0505 (7)	0.0591 (8)	0.0897 (10)	−0.0204 (6)	0.0263 (7)	−0.0248 (7)
S1	0.0480 (3)	0.0784 (4)	0.0390 (2)	−0.0091 (2)	0.02147 (19)	−0.0101 (2)
S2	0.0341 (2)	0.0642 (3)	0.0365 (2)	0.00106 (18)	0.00896 (16)	0.00165 (19)

C1—H1A	0.9700	C8—H8	0.9800
C1—H1B	0.9700	C8—S1	1.8268 (15)
C1—C6	1.516 (2)	C8—S2	1.7976 (15)
C1—N3	1.460 (2)	C9—H9A	0.9700
C2—H2A	0.9700	C9—H9B	0.9700
C2—H2B	0.9700	C9—C10	1.499 (3)
C2—N2	1.465 (2)	C9—S2	1.791 (2)
C2—N3	1.440 (2)	C10—H10B	0.9700
C3—H3B	0.9700	C10—H10A	0.9700
C3—H3A	0.9700	C10—S1	1.8078 (19)
C3—C4	1.512 (2)	C11—H11A	0.9700
C3—N2	1.458 (2)	C11—H11B	0.9700
C4—H4A	0.9700	C11—C12	1.509 (3)
C4—H4B	0.9700	C11—N3	1.473 (2)
C4—N1	1.483 (2)	C12—H12B	0.9700
C5—C6	1.413 (2)	C12—H12A	0.9700
C5—N1	1.3617 (18)	C12—C13	1.486 (3)
C5—N2	1.3269 (19)	C13—H13B	0.9600
C6—N4	1.359 (2)	C13—H13C	0.9600
C7—H7B	0.9700	C13—H13A	0.9600
C7—H7A	0.9700	N4—O1	1.2550 (16)
C7—C8	1.529 (2)	N4—O2	1.2674 (16)
C7—N1	1.4576 (19)
C1—N3—C11	112.44 (14)	C12—C13—H13A	109.5
H1A—C1—H1B	107.8	H12B—C12—H12A	107.8
C2—N3—C1	108.50 (13)	C13—C12—C11	112.7 (2)
C2—N3—C11	112.60 (14)	C13—C12—H12B	109.0
H2A—C2—H2B	108.0	C13—C12—H12A	109.0
C3—C4—H4A	110.8	H13B—C13—H13C	109.5
C3—C4—H4B	110.8	H13B—C13—H13A	109.5
C3—N2—C2	124.84 (14)	H13C—C13—H13A	109.5
H3B—C3—H3A	109.3	N1—C4—C3	104.87 (12)
C4—C3—H3B	111.4	N1—C4—H4A	110.8
C4—C3—H3A	111.4	N1—C4—H4B	110.8
H4A—C4—H4B	108.8	N1—C5—C6	130.82 (14)
C5—C6—C1	119.04 (14)	N1—C7—H7B	108.7
C5—N1—C4	108.19 (12)	N1—C7—H7A	108.7
C5—N1—C7	122.63 (12)	N1—C7—C8	114.33 (12)
C5—N2—C2	121.37 (13)	N2—C2—H2A	109.3
C5—N2—C3	112.42 (13)	N2—C2—H2B	109.3
C6—C1—H1A	109.0	N2—C3—H3B	111.4
C6—C1—H1B	109.0	N2—C3—H3A	111.4
C7—C8—H8	108.3	N2—C3—C4	101.72 (13)
C7—C8—S1	108.97 (10)	N2—C5—C6	118.30 (13)
C7—C8—S2	114.96 (11)	N2—C5—N1	110.84 (13)
C7—N1—C4	119.23 (13)	N3—C1—H1A	109.0
H7B—C7—H7A	107.6	N3—C1—H1B	109.0
C8—C7—H7B	108.7	N3—C1—C6	112.87 (13)
C8—C7—H7A	108.7	N3—C2—H2A	109.3
C9—C10—H10B	109.6	N3—C2—H2B	109.3
C9—C10—H10A	109.6	N3—C2—N2	111.46 (13)
C9—C10—S1	110.31 (13)	N3—C11—H11A	109.0
C9—S2—C8	94.61 (8)	N3—C11—H11B	109.0
H9A—C9—H9B	108.4	N3—C11—C12	112.74 (16)
C10—C9—H9A	110.1	N4—C6—C1	117.12 (13)
C10—C9—H9B	110.1	N4—C6—C5	123.19 (13)
C10—C9—S2	108.21 (15)	O1—N4—C6	122.64 (13)
C10—S1—C8	97.79 (9)	O1—N4—O2	120.23 (13)
H10B—C10—H10A	108.1	O2—N4—C6	117.06 (13)
C11—C12—H12B	109.0	S1—C8—H8	108.3
C11—C12—H12A	109.0	S1—C10—H10B	109.6
H11A—C11—H11B	107.8	S1—C10—H10A	109.6
C12—C11—H11A	109.0	S2—C8—H8	108.3
C12—C11—H11B	109.0	S2—C8—S1	107.87 (8)
C12—C13—H13B	109.5	S2—C9—H9A	110.1
C12—C13—H13C	109.5	S2—C9—H9B	110.1
C1—C6—N4—O1	−172.73 (14)	N1—C5—C6—C1	−163.47 (15)
C1—C6—N4—O2	4.3 (2)	N1—C5—C6—N4	26.1 (3)
C3—C4—N1—C5	−10.33 (17)	N1—C5—N2—C2	174.29 (13)
C3—C4—N1—C7	136.21 (14)	N1—C5—N2—C3	7.03 (18)
C4—C3—N2—C2	−179.65 (14)	N1—C7—C8—S1	179.15 (10)
C4—C3—N2—C5	−12.91 (17)	N1—C7—C8—S2	−59.67 (16)
C5—C6—N4—O1	−2.1 (2)	N2—C2—N3—C1	59.98 (18)
C5—C6—N4—O2	174.92 (14)	N2—C2—N3—C11	−65.14 (19)
C6—C1—N3—C2	−49.56 (18)	N2—C3—C4—N1	13.31 (16)
C6—C1—N3—C11	75.65 (17)	N2—C5—C6—C1	14.4 (2)
C6—C5—N1—C4	−179.54 (15)	N2—C5—C6—N4	−156.09 (15)
C6—C5—N1—C7	35.3 (2)	N2—C5—N1—C4	2.50 (17)
C6—C5—N2—C2	−4.0 (2)	N2—C5—N1—C7	−142.66 (14)
C6—C5—N2—C3	−171.22 (13)	N3—C1—C6—C5	13.5 (2)
C7—C8—S1—C10	109.21 (13)	N3—C1—C6—N4	−175.50 (14)
C7—C8—S2—C9	−86.58 (13)	N3—C2—N2—C3	131.22 (16)
C8—C7—N1—C4	91.93 (16)	N3—C2—N2—C5	−34.4 (2)
C8—C7—N1—C5	−126.53 (15)	N3—C11—C12—C13	69.8 (2)
C9—C10—S1—C8	−14.29 (18)	S1—C8—S2—C9	35.20 (11)
C10—C9—S2—C8	−46.45 (16)	S2—C8—S1—C10	−16.21 (11)
C12—C11—N3—C1	82.0 (2)	S2—C9—C10—S1	40.3 (2)
C12—C11—N3—C2	−155.08 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1i	0.97	2.48	3.322 (2)	145
C3—H3B···O1ii	0.97	2.56	3.269 (2)	130
C4—H4A···O2i	0.97	2.52	3.449 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1i	0.97	2.48	3.322 (2)	145
C3—H3B⋯O1ii	0.97	2.56	3.269 (2)	130
C4—H4A⋯O2i	0.97	2.52	3.449 (2)	160

Symmetry codes: (i) ; (ii) .