(E)-1-[1-(4-Chloro­phen­yl)eth­yl]-3,5-dimethyl-N-nitro-1,3,5-triazinan-2-imine

Su, H.; Xu, L.

doi:10.1107/S1600536810046246

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3201

https://doi.org/10.1107/S1600536810046246

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(E)-1-[1-(4-Chlorophenyl)ethyl]-3,5-dimethyl-N-nitro-1,3,5-triazinan-2-imine

Huai-gang Su ^a and Liang-zhong Xu ^a ^*

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: qknhs@yahoo.com.cn

(Received 4 November 2010; accepted 9 November 2010; online 17 November 2010)

In the title compound, C₁₃H₁₈ClN₅O₂, the 1,3,5-triazinane ring exhibits an envelope conformation with an E form. The chlorophenyl 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 intermolecular 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_r = 311.77
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.104
S = 1.08
2585 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.51 e Å⁻³

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) x+1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046246/dn2619Isup2.hkl

checkCIF report

Comment top

The title compound was synthesized as a new compound with better insecticide activity. Lots of similar insecticide compounds with (I) were synthesized (Koln et al., 2002). We report here the crystal struture of (I).

The 1,3,5-triazinan ring exhibits envelope conformation with puckering parameters Q= 0.4777 (19)Å, θ= 57.8 (2)° and φ= 238.5 (3)° (Cremer & Pople, 1975). The chlorophenyl ring as well as the nitro group are twisted with respect to the mean plane of the triazinan ring making dihedral angles of 67.30 (9)° and 83.54 (8)° respectively (Fig. 1). All bond lengths and angles are normal and in a good agreement with those recently reported (Hu et al., 2008; Zhao et al., 2008; Xu et al., 2010).

Weak intermolecular C–H···O hydrogen bonds build up a corrugated layer parallel to the (1 0 1) plane (Table 1).

Related literature top

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 top

A mixture of 1,5-dimethyl-2-(nitromethylene)-1,3,5-triazinane (20.64 g, 0.12 mol), potassium carbonate (20.7 g, 0.15 mol), potassium iodization (2 g) and ethyl acetate (150 ml) was stirred and heated in a 500 ml flask. The mixture was slowly heated to 353 K - 363 K and kept for 1 h. Then ,1-chloro-4-(1-chloroethyl)benzene (21 g, 0.12 mol, dissolved in 100 ml of ethyl acetate) was added dropwise into the flask, and the mixture was futher stirred at 353 K - 363 K for 15 h. After cooling, the precipitate was filtered,washed with ethyl acetate and water, and recrystallized from ethyl acetate to obtain flaxen powder. Yield: 86%.

Structure description top

Weak intermolecular C–H···O hydrogen bonds build up a corrugated layer parallel to the (1 0 1) plane (Table 1).

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).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound (I) with the atoms labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

(E)-1-[1-(4-Chlorophenyl)ethyl]-3,5-dimethyl-N-nitro-1,3,5- triazinan-2-imine top

Crystal data top

C₁₃H₁₈ClN₅O₂	F(000) = 656
M_r = 311.77	D_x = 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

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2585 independent reflections
Radiation source: rotating anode	2303 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.039
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 1.4°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −35→34
T_min = 0.947, T_max = 0.968	l = −8→8
9753 measured reflections

Refinement top

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(F_o²) + (0.0488P)² + 0.7943P] where P = (F_o² + 2F_c²)/3
2585 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₃H₁₈ClN₅O₂	V = 1467.4 (5) Å³
M_r = 311.77	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.2483 (14) Å	µ = 0.27 mm⁻¹
b = 29.568 (6) Å	T = 113 K
c = 7.2306 (14) Å	0.20 × 0.16 × 0.12 mm
β = 108.75 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2585 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2303 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.968	R_int = 0.039
9753 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.08	Δρ_max = 0.46 e Å⁻³
2585 reflections	Δρ_min = −0.51 e Å⁻³
193 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₈ClN₅O₂
M_r	311.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	7.2483 (14), 29.568 (6), 7.2306 (14)
β (°)	108.75 (3)
V (Å³)	1467.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.20 × 0.16 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.947, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	9753, 2585, 2303
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.104, 1.08
No. of reflections	2585
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.51

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXTL (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2ⁱ	0.98	2.29	3.273 (2)	177.8
C10—H10A···O1ⁱⁱ	0.99	2.43	3.278 (2)	142.9
C11—H11B···O2ⁱ	0.99	2.49	3.434 (3)	160.0

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z−1/2.

References

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
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Volume 66| Part 12| December 2010| Page o3201

https://doi.org/10.1107/S1600536810046246

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-1-[1-(4-Chloro­phen­yl)eth­yl]-3,5-di­methyl-N-nitro-1,3,5-triazinan-2-imine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(E)-1-[1-(4-Chlorophenyl)ethyl]-3,5-dimethyl-N-nitro-1,3,5-triazinan-2-imine