rac-(E)-3-[1-(2-Chloro-phen-yl)eth-yl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine.

In the title compound, C(12)H(15)ClN(4)O(3), which has potential insecticidal activity, the oxadiazine ring and the benzene ring make a dihedral angle of 84.63 (2)° to one another. The crystal packing involves weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the biological activity of oxadiazine derivatives, see: Maienfisch & Huerlimann (1994 ▶); Gsell & Maienfisch (1998 ▶). For the synthesis, see: Gottfied et al. (2001 ▶). For related structures, see: Chopra et al. (2004 ▶); Kang et al. (2008 ▶); Zhong et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C12H15ClN4O3

M = 298.73

Monoclinic,

a = 17.259 (4) Å

b = 6.9157 (14) Å

c = 12.169 (2) Å

β = 109.63 (3)°

V = 1368.0 (5) Å3

Z = 4

Cu Kα radiation

μ = 2.61 mm−1

T = 113 K

0.26 × 0.22 × 0.18 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.550, T max = 0.651

12087 measured reflections

2590 independent reflections

2562 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 1.08

2590 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034343/zs2061sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034343/zs2061Isup2.hkl

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

C12H15ClN4O3	F(000) = 624
Mr = 298.73	Dx = 1.450 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybc	Cell parameters from 1058 reflections
a = 17.259 (4) Å	θ = 27.5–71.9°
b = 6.9157 (14) Å	µ = 2.61 mm−1
c = 12.169 (2) Å	T = 113 K
β = 109.63 (3)°	Block, colorless
V = 1368.0 (5) Å3	0.26 × 0.22 × 0.18 mm
Z = 4

Rigaku Saturn diffractometer	2590 independent reflections
Radiation source: fine-focus sealed tube	2562 reflections with I > 2σ(I)
graphite	Rint = 0.054
Detector resolution: 14.63 pixels mm-1	θmax = 72.1°, θmin = 2.7°
ω scans	h = −20→21
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −8→8
Tmin = 0.550, Tmax = 0.651	l = −13→14
12087 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.058P)2 + 0.6637P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2590 reflections	Δρmax = 0.26 e Å−3
184 parameters	Δρmin = −0.37 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0057 (11)

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
Cl1	0.36163 (2)	0.37729 (6)	−0.00540 (3)	0.02744 (17)
N1	0.09670 (7)	0.33360 (16)	−0.04098 (10)	0.0152 (3)
N2	0.21260 (7)	0.48468 (16)	0.08081 (10)	0.0146 (3)
N3	0.19653 (7)	0.15435 (16)	0.10592 (10)	0.0165 (3)
N4	0.15382 (7)	0.09523 (17)	0.17188 (10)	0.0172 (3)
O1	0.09734 (6)	0.67120 (14)	−0.01841 (9)	0.0180 (2)
O2	0.09602 (7)	0.19372 (16)	0.18398 (9)	0.0247 (3)
O3	0.17457 (7)	−0.06237 (15)	0.22426 (9)	0.0238 (3)
C1	0.06227 (8)	0.5189 (2)	−0.09525 (12)	0.0171 (3)
H1A	0.0740	0.5363	−0.1689	0.021*
H1B	0.0018	0.5188	−0.1139	0.021*
C2	0.16607 (8)	0.32676 (19)	0.04897 (12)	0.0138 (3)
C3	0.18404 (8)	0.66306 (19)	0.01450 (13)	0.0172 (3)
H3A	0.2089	0.7767	0.0630	0.021*
H3B	0.2007	0.6644	−0.0558	0.021*
C4	0.04698 (9)	0.1625 (2)	−0.08861 (13)	0.0196 (3)
H4A	0.0801	0.0459	−0.0611	0.029*
H4B	0.0285	0.1670	−0.1740	0.029*
H4C	−0.0010	0.1599	−0.0626	0.029*
C5	0.28920 (8)	0.48416 (19)	0.18389 (12)	0.0171 (3)
H5	0.3141	0.3524	0.1894	0.020*
C6	0.26984 (10)	0.5185 (2)	0.29596 (12)	0.0225 (3)
H6A	0.3212	0.5198	0.3627	0.034*
H6B	0.2342	0.4147	0.3061	0.034*
H6C	0.2418	0.6430	0.2910	0.034*
C7	0.34952 (8)	0.6269 (2)	0.16156 (13)	0.0184 (3)
C8	0.38573 (9)	0.5900 (2)	0.07689 (13)	0.0209 (3)
C9	0.44068 (9)	0.7161 (2)	0.05401 (14)	0.0257 (4)
H9	0.4640	0.6869	−0.0045	0.031*
C10	0.46123 (10)	0.8863 (2)	0.11817 (16)	0.0305 (4)
H10	0.4997	0.9733	0.1048	0.037*
C11	0.42544 (10)	0.9287 (2)	0.20160 (15)	0.0308 (4)
H11	0.4389	1.0459	0.2445	0.037*
C12	0.37004 (9)	0.8007 (2)	0.22283 (13)	0.0247 (3)
H12	0.3457	0.8320	0.2800	0.030*

	U11	U22	U33	U12	U13	U23
Cl1	0.0282 (2)	0.0206 (2)	0.0376 (3)	−0.00083 (13)	0.01641 (18)	−0.00617 (14)
N1	0.0166 (6)	0.0106 (5)	0.0167 (6)	−0.0008 (4)	0.0035 (4)	−0.0001 (4)
N2	0.0146 (5)	0.0095 (5)	0.0179 (6)	0.0011 (4)	0.0029 (4)	0.0012 (4)
N3	0.0171 (6)	0.0104 (5)	0.0226 (6)	0.0015 (4)	0.0075 (5)	0.0038 (4)
N4	0.0216 (6)	0.0110 (5)	0.0182 (6)	0.0015 (5)	0.0058 (5)	0.0019 (4)
O1	0.0167 (5)	0.0119 (5)	0.0225 (5)	0.0038 (4)	0.0030 (4)	−0.0010 (4)
O2	0.0286 (6)	0.0209 (6)	0.0301 (6)	0.0107 (4)	0.0170 (5)	0.0072 (4)
O3	0.0338 (6)	0.0117 (5)	0.0275 (6)	0.0059 (4)	0.0123 (4)	0.0083 (4)
C1	0.0168 (6)	0.0134 (6)	0.0183 (7)	0.0022 (5)	0.0021 (5)	0.0009 (5)
C2	0.0156 (6)	0.0100 (6)	0.0173 (6)	0.0016 (5)	0.0077 (5)	−0.0003 (5)
C3	0.0165 (7)	0.0099 (6)	0.0226 (7)	0.0010 (5)	0.0032 (5)	0.0035 (5)
C4	0.0204 (7)	0.0144 (6)	0.0222 (7)	−0.0049 (5)	0.0048 (6)	−0.0024 (5)
C5	0.0163 (6)	0.0123 (6)	0.0190 (7)	0.0019 (5)	0.0011 (5)	0.0014 (5)
C6	0.0274 (7)	0.0183 (7)	0.0192 (7)	0.0004 (6)	0.0042 (6)	0.0019 (5)
C7	0.0149 (6)	0.0136 (7)	0.0216 (7)	0.0010 (5)	−0.0006 (5)	0.0026 (5)
C8	0.0157 (6)	0.0157 (7)	0.0270 (8)	0.0018 (5)	0.0015 (6)	0.0030 (6)
C9	0.0182 (7)	0.0267 (8)	0.0298 (8)	0.0013 (6)	0.0047 (6)	0.0093 (6)
C10	0.0211 (8)	0.0248 (8)	0.0372 (9)	−0.0083 (6)	−0.0013 (7)	0.0108 (7)
C11	0.0302 (8)	0.0187 (7)	0.0325 (9)	−0.0086 (7)	−0.0042 (7)	0.0003 (6)
C12	0.0249 (7)	0.0185 (7)	0.0242 (7)	−0.0029 (6)	−0.0004 (6)	−0.0013 (6)

Cl1—C8	1.7492 (16)	C4—H4B	0.9800
N1—C2	1.324 (2)	C4—H4C	0.9800
N1—C4	1.4621 (17)	C5—C7	1.524 (2)
N1—C1	1.4721 (17)	C5—C6	1.528 (2)
N2—C2	1.3336 (18)	C5—H5	1.0000
N2—C3	1.4658 (16)	C6—H6A	0.9800
N2—C5	1.4856 (17)	C6—H6B	0.9800
N3—N4	1.3237 (17)	C6—H6C	0.9800
N3—C2	1.3904 (17)	C7—C12	1.396 (2)
N4—O3	1.2526 (15)	C7—C8	1.396 (2)
N4—O2	1.2567 (16)	C8—C9	1.384 (2)
O1—C1	1.4037 (17)	C9—C10	1.391 (2)
O1—C3	1.4143 (18)	C9—H9	0.9500
C1—H1A	0.9900	C10—C11	1.386 (3)
C1—H1B	0.9900	C10—H10	0.9500
C3—H3A	0.9900	C11—C12	1.389 (2)
C3—H3B	0.9900	C11—H11	0.9500
C4—H4A	0.9800	C12—H12	0.9500
C2—N1—C4	123.09 (11)	H4B—C4—H4C	109.5
C2—N1—C1	121.23 (11)	N2—C5—C7	108.38 (11)
C4—N1—C1	115.58 (11)	N2—C5—C6	110.73 (11)
C2—N2—C3	118.10 (11)	C7—C5—C6	115.21 (12)
C2—N2—C5	121.43 (11)	N2—C5—H5	107.4
C3—N2—C5	120.40 (11)	C7—C5—H5	107.4
N4—N3—C2	111.90 (11)	C6—C5—H5	107.4
O3—N4—O2	120.96 (12)	C5—C6—H6A	109.5
O3—N4—N3	117.07 (11)	C5—C6—H6B	109.5
O2—N4—N3	121.95 (11)	H6A—C6—H6B	109.5
C1—O1—C3	109.70 (10)	C5—C6—H6C	109.5
O1—C1—N1	109.62 (11)	H6A—C6—H6C	109.5
O1—C1—H1A	109.7	H6B—C6—H6C	109.5
N1—C1—H1A	109.7	C12—C7—C8	117.08 (14)
O1—C1—H1B	109.7	C12—C7—C5	121.90 (14)
N1—C1—H1B	109.7	C8—C7—C5	121.02 (13)
H1A—C1—H1B	108.2	C9—C8—C7	122.70 (14)
N1—C2—N2	119.99 (12)	C9—C8—Cl1	117.52 (13)
N1—C2—N3	121.87 (12)	C7—C8—Cl1	119.78 (11)
N2—C2—N3	117.88 (12)	C8—C9—C10	118.89 (16)
O1—C3—N2	108.51 (11)	C8—C9—H9	120.6
O1—C3—H3A	110.0	C10—C9—H9	120.6
N2—C3—H3A	110.0	C11—C10—C9	119.87 (15)
O1—C3—H3B	110.0	C11—C10—H10	120.1
N2—C3—H3B	110.0	C9—C10—H10	120.1
H3A—C3—H3B	108.4	C10—C11—C12	120.38 (15)
N1—C4—H4A	109.5	C10—C11—H11	119.8
N1—C4—H4B	109.5	C12—C11—H11	119.8
H4A—C4—H4B	109.5	C11—C12—C7	121.07 (16)
N1—C4—H4C	109.5	C11—C12—H12	119.5
H4A—C4—H4C	109.5	C7—C12—H12	119.5
C2—N3—N4—O3	177.78 (11)	C3—N2—C5—C7	−33.89 (16)
C2—N3—N4—O2	−3.68 (18)	C2—N2—C5—C6	−83.61 (15)
C3—O1—C1—N1	55.36 (14)	C3—N2—C5—C6	93.38 (14)
C2—N1—C1—O1	−18.08 (18)	N2—C5—C7—C12	110.06 (14)
C4—N1—C1—O1	158.55 (12)	C6—C5—C7—C12	−14.60 (19)
C4—N1—C2—N2	173.37 (12)	N2—C5—C7—C8	−68.88 (16)
C1—N1—C2—N2	−10.3 (2)	C6—C5—C7—C8	166.46 (13)
C4—N1—C2—N3	−0.6 (2)	C12—C7—C8—C9	0.9 (2)
C1—N1—C2—N3	175.73 (12)	C5—C7—C8—C9	179.93 (13)
C3—N2—C2—N1	0.66 (19)	C12—C7—C8—Cl1	−178.83 (10)
C5—N2—C2—N1	177.72 (12)	C5—C7—C8—Cl1	0.15 (18)
C3—N2—C2—N3	174.91 (11)	C7—C8—C9—C10	0.4 (2)
C5—N2—C2—N3	−8.03 (19)	Cl1—C8—C9—C10	−179.86 (11)
N4—N3—C2—N1	−73.97 (16)	C8—C9—C10—C11	−1.3 (2)
N4—N3—C2—N2	111.90 (14)	C9—C10—C11—C12	1.0 (2)
C1—O1—C3—N2	−64.67 (14)	C10—C11—C12—C7	0.4 (2)
C2—N2—C3—O1	36.13 (16)	C8—C7—C12—C11	−1.3 (2)
C5—N2—C3—O1	−140.96 (12)	C5—C7—C12—C11	179.72 (13)
C2—N2—C5—C7	149.11 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2i	0.99	2.52	3.2817 (18)	134.
C1—H1A···O3i	0.99	2.50	3.396 (2)	150.
C1—H1B···O2ii	0.99	2.56	3.2555 (18)	127.
C3—H3A···O3iii	0.99	2.49	3.2294 (19)	131.
C4—H4B···O2i	0.98	2.57	3.3070 (19)	132.
C4—H4C···O1ii	0.98	2.49	3.377 (2)	150.
C6—H6C···O3iii	0.98	2.35	3.3020 (19)	164.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2i	0.99	2.52	3.2817 (18)	134
C1—H1A⋯O3i	0.99	2.50	3.396 (2)	150
C1—H1B⋯O2ii	0.99	2.56	3.2555 (18)	127
C3—H3A⋯O3iii	0.99	2.49	3.2294 (19)	131
C4—H4B⋯O2i	0.98	2.57	3.3070 (19)	132
C4—H4C⋯O1ii	0.98	2.49	3.377 (2)	150
C6—H6C⋯O3iii	0.98	2.35	3.3020 (19)	164

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