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

In the title compound, C(13)H(18)ClN(5)O(2), the 1,3,5-triazinane ring exhibits an envelope conformation with an E form. The chloro-phenyl ring and the nitro group are each twisted with respect to the mean plane of the triazinane ring, making dihedral angles of 67.30 (9) and 83.54 (8)°, respectively. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds build up a corrugated layer parallel to the (101) plane.

Related literature

The title compound was synthesized as a new compound with better insecticidal activity. For similar compounds with insecticidal properties, see: Koln et al. (2002 ▶). For related structures, see: Zhao et al. (2008 ▶); Hu et al. (2008 ▶); Xu et al. (2010 ▶) For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C13H18ClN5O2

M = 311.77

Monoclinic,

a = 7.2483 (14) Å

b = 29.568 (6) Å

c = 7.2306 (14) Å

β = 108.75 (3)°

V = 1467.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 113 K

0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.947, T max = 0.968

9753 measured reflections

2585 independent reflections

2303 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.104

S = 1.08

2585 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.51 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, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046246/dn2619sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046246/dn2619Isup2.hkl

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

C13H18ClN5O2	F(000) = 656
Mr = 311.77	Dx = 1.411 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3278 reflections
a = 7.2483 (14) Å	θ = 1.4–27.9°
b = 29.568 (6) Å	µ = 0.27 mm−1
c = 7.2306 (14) Å	T = 113 K
β = 108.75 (3)°	Needle, colourless
V = 1467.4 (5) Å3	0.20 × 0.16 × 0.12 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	2585 independent reflections
Radiation source: rotating anode	2303 reflections with I > 2σ(I)
confocal	Rint = 0.039
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 1.4°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −35→34
Tmin = 0.947, Tmax = 0.968	l = −8→8
9753 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0488P)2 + 0.7943P] where P = (Fo2 + 2Fc2)/3
2585 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.37472 (9)	0.56523 (2)	0.15716 (10)	0.0546 (2)
O1	−0.25418 (19)	0.29503 (4)	0.41241 (18)	0.0236 (3)
O2	−0.48276 (18)	0.33395 (5)	0.47562 (18)	0.0254 (3)
N1	−0.0516 (2)	0.36893 (5)	0.2166 (2)	0.0173 (3)
N2	−0.2858 (2)	0.32380 (5)	0.0044 (2)	0.0175 (3)
N3	0.0492 (2)	0.31375 (5)	0.0208 (2)	0.0181 (3)
N4	−0.3580 (2)	0.36095 (5)	0.2595 (2)	0.0197 (3)
N5	−0.3641 (2)	0.32910 (5)	0.3838 (2)	0.0181 (3)
C1	0.3035 (3)	0.44147 (6)	0.3422 (3)	0.0261 (4)
H1	0.3813	0.4153	0.3853	0.031*
C2	0.3844 (3)	0.47936 (7)	0.2862 (3)	0.0321 (5)
H2	0.5159	0.4789	0.2876	0.038*
C3	0.2725 (3)	0.51775 (7)	0.2283 (3)	0.0323 (5)
C4	0.0823 (3)	0.51896 (7)	0.2250 (3)	0.0326 (5)
H4	0.0071	0.5457	0.1871	0.039*
C5	0.0016 (3)	0.48064 (6)	0.2776 (3)	0.0265 (4)
H5	−0.1307	0.4813	0.2736	0.032*
C6	0.1093 (3)	0.44127 (6)	0.3362 (3)	0.0206 (4)
C7	0.0118 (3)	0.39993 (6)	0.3875 (3)	0.0200 (4)
H7	−0.1081	0.4105	0.4143	0.024*
C8	0.1367 (3)	0.37472 (6)	0.5690 (3)	0.0231 (4)
H8A	0.2520	0.3622	0.5446	0.035*
H8B	0.0605	0.3501	0.5991	0.035*
H8C	0.1776	0.3957	0.6797	0.035*
C9	−0.2273 (2)	0.34984 (5)	0.1609 (2)	0.0166 (4)
C10	−0.1503 (3)	0.31248 (6)	−0.1043 (3)	0.0199 (4)
H10A	−0.1808	0.2819	−0.1616	0.024*
H10B	−0.1683	0.3343	−0.2127	0.024*
C11	0.0888 (3)	0.35748 (6)	0.1119 (3)	0.0184 (4)
H11A	0.0810	0.3807	0.0110	0.022*
H11B	0.2229	0.3578	0.2056	0.022*
C12	0.0994 (3)	0.27654 (6)	0.1633 (3)	0.0231 (4)
H12A	0.0757	0.2475	0.0940	0.035*
H12B	0.0188	0.2785	0.2489	0.035*
H12C	0.2373	0.2787	0.2420	0.035*
C13	−0.4771 (3)	0.30192 (6)	−0.0593 (3)	0.0226 (4)
H13A	−0.5701	0.3204	−0.0193	0.034*
H13B	−0.4672	0.2719	0.0007	0.034*
H13C	−0.5222	0.2988	−0.2018	0.034*

	U11	U22	U33	U12	U13	U23
Cl1	0.0535 (4)	0.0359 (3)	0.0547 (4)	−0.0206 (3)	−0.0102 (3)	0.0202 (3)
O1	0.0254 (7)	0.0221 (7)	0.0255 (7)	0.0071 (5)	0.0111 (6)	0.0057 (5)
O2	0.0188 (7)	0.0410 (8)	0.0203 (7)	0.0038 (6)	0.0120 (5)	0.0028 (6)
N1	0.0174 (8)	0.0186 (7)	0.0171 (7)	0.0002 (6)	0.0071 (6)	−0.0011 (6)
N2	0.0142 (7)	0.0210 (8)	0.0176 (7)	0.0000 (6)	0.0057 (6)	0.0004 (6)
N3	0.0165 (8)	0.0198 (8)	0.0185 (7)	−0.0008 (6)	0.0062 (6)	−0.0019 (6)
N4	0.0190 (8)	0.0220 (8)	0.0207 (8)	0.0039 (6)	0.0100 (6)	0.0035 (6)
N5	0.0151 (7)	0.0233 (8)	0.0155 (7)	0.0002 (6)	0.0045 (6)	−0.0007 (6)
C1	0.0241 (10)	0.0198 (9)	0.0300 (10)	−0.0014 (7)	0.0026 (8)	0.0005 (8)
C2	0.0260 (11)	0.0310 (11)	0.0346 (11)	−0.0077 (8)	0.0033 (9)	0.0021 (9)
C3	0.0390 (12)	0.0229 (10)	0.0254 (10)	−0.0100 (9)	−0.0032 (9)	0.0030 (8)
C4	0.0439 (13)	0.0204 (10)	0.0262 (11)	0.0063 (9)	0.0012 (9)	0.0000 (8)
C5	0.0286 (10)	0.0269 (10)	0.0223 (10)	0.0049 (8)	0.0059 (8)	−0.0039 (8)
C6	0.0249 (10)	0.0188 (9)	0.0164 (9)	−0.0012 (7)	0.0044 (7)	−0.0038 (7)
C7	0.0206 (9)	0.0214 (9)	0.0184 (9)	0.0015 (7)	0.0067 (7)	−0.0046 (7)
C8	0.0247 (10)	0.0262 (10)	0.0189 (9)	−0.0005 (8)	0.0075 (8)	−0.0005 (7)
C9	0.0175 (9)	0.0155 (8)	0.0165 (8)	0.0039 (7)	0.0052 (7)	0.0038 (7)
C10	0.0196 (9)	0.0253 (10)	0.0159 (8)	−0.0008 (7)	0.0073 (7)	−0.0021 (7)
C11	0.0175 (9)	0.0204 (9)	0.0195 (9)	−0.0012 (7)	0.0088 (7)	−0.0010 (7)
C12	0.0223 (10)	0.0215 (9)	0.0250 (10)	0.0027 (7)	0.0070 (8)	0.0004 (7)
C13	0.0146 (9)	0.0290 (10)	0.0232 (9)	−0.0024 (7)	0.0045 (7)	−0.0022 (8)

Cl1—C3	1.740 (2)	C4—C5	1.383 (3)
O1—N5	1.2595 (19)	C4—H4	0.9500
O2—N5	1.2522 (19)	C5—C6	1.390 (3)
N1—C9	1.332 (2)	C5—H5	0.9500
N1—C7	1.488 (2)	C6—C7	1.516 (3)
N1—C11	1.490 (2)	C7—C8	1.527 (3)
N2—C9	1.321 (2)	C7—H7	1.0000
N2—C13	1.464 (2)	C8—H8A	0.9800
N2—C10	1.480 (2)	C8—H8B	0.9800
N3—C11	1.437 (2)	C8—H8C	0.9800
N3—C10	1.439 (2)	C10—H10A	0.9900
N3—C12	1.471 (2)	C10—H10B	0.9900
N4—N5	1.312 (2)	C11—H11A	0.9900
N4—C9	1.395 (2)	C11—H11B	0.9900
C1—C2	1.384 (3)	C12—H12A	0.9800
C1—C6	1.394 (3)	C12—H12B	0.9800
C1—H1	0.9500	C12—H12C	0.9800
C2—C3	1.379 (3)	C13—H13A	0.9800
C2—H2	0.9500	C13—H13B	0.9800
C3—C4	1.372 (3)	C13—H13C	0.9800
C9—N1—C7	121.49 (14)	C6—C7—H7	107.3
C9—N1—C11	119.58 (14)	C8—C7—H7	107.3
C7—N1—C11	118.87 (13)	C7—C8—H8A	109.5
C9—N2—C13	122.48 (15)	C7—C8—H8B	109.5
C9—N2—C10	120.15 (14)	H8A—C8—H8B	109.5
C13—N2—C10	117.16 (14)	C7—C8—H8C	109.5
C11—N3—C10	108.91 (14)	H8A—C8—H8C	109.5
C11—N3—C12	112.59 (14)	H8B—C8—H8C	109.5
C10—N3—C12	113.18 (14)	N2—C9—N1	121.19 (15)
N5—N4—C9	111.03 (14)	N2—C9—N4	119.45 (15)
O2—N5—O1	120.71 (14)	N1—C9—N4	119.10 (15)
O2—N5—N4	117.46 (14)	N3—C10—N2	111.35 (14)
O1—N5—N4	121.83 (14)	N3—C10—H10A	109.4
C2—C1—C6	120.84 (18)	N2—C10—H10A	109.4
C2—C1—H1	119.6	N3—C10—H10B	109.4
C6—C1—H1	119.6	N2—C10—H10B	109.4
C3—C2—C1	119.5 (2)	H10A—C10—H10B	108.0
C3—C2—H2	120.3	N3—C11—N1	111.63 (14)
C1—C2—H2	120.3	N3—C11—H11A	109.3
C4—C3—C2	121.07 (19)	N1—C11—H11A	109.3
C4—C3—Cl1	119.65 (16)	N3—C11—H11B	109.3
C2—C3—Cl1	119.28 (18)	N1—C11—H11B	109.3
C3—C4—C5	119.04 (18)	H11A—C11—H11B	108.0
C3—C4—H4	120.5	N3—C12—H12A	109.5
C5—C4—H4	120.5	N3—C12—H12B	109.5
C4—C5—C6	121.61 (19)	H12A—C12—H12B	109.5
C4—C5—H5	119.2	N3—C12—H12C	109.5
C6—C5—H5	119.2	H12A—C12—H12C	109.5
C5—C6—C1	117.94 (17)	H12B—C12—H12C	109.5
C5—C6—C7	119.32 (17)	N2—C13—H13A	109.5
C1—C6—C7	122.73 (16)	N2—C13—H13B	109.5
N1—C7—C6	109.73 (14)	H13A—C13—H13B	109.5
N1—C7—C8	110.65 (14)	N2—C13—H13C	109.5
C6—C7—C8	114.18 (15)	H13A—C13—H13C	109.5
N1—C7—H7	107.3	H13B—C13—H13C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2i	0.98	2.29	3.273 (2)	178
C10—H10A···O1ii	0.99	2.43	3.278 (2)	143
C11—H11B···O2i	0.99	2.49	3.434 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2i	0.98	2.29	3.273 (2)	178
C10—H10A⋯O1ii	0.99	2.43	3.278 (2)	143
C11—H11B⋯O2i	0.99	2.49	3.434 (3)	160

Symmetry codes: (i) ; (ii) .