3-[(E)-3,7-Dimethyl-octa-2,6-dien-yl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine.

The title compound, C(14)H(24)N(4)O(3), was synthesized by the reaction of geranyl and 3-methyl-4-nitro-imino-1,3,5-oxadiazinane. In the crystal structure, mol-ecules are assembled by weak inter-molecular C-H⋯O hydrogen bonds. The nitryl and the long carbon chain are located on the same side of the C=N bond due to the two weak intra-molecular C-H⋯N hydrogen bonds; the configuration of the oxadiazinane is Z.

Related literature

For background literature, see: Bowers et al. (1972 ▶). For related literature, see: Yang et al. (2004 ▶); Van Oosten et al. (1990 ▶).

Experimental

Crystal data

C14H24N4O3

M = 296.37

Monoclinic,

a = 7.9318 (16) Å

b = 6.6423 (13) Å

c = 31.191 (7) Å

β = 99.55 (3)°

V = 1620.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.60 × 0.30 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.943, T max = 0.993

7692 measured reflections

2825 independent reflections

1306 reflections with I > 2σ(I)

R int = 0.0508

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.152

S = 0.84

2825 reflections

194 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.30 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2000 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2000 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801492X/rk2083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801492X/rk2083Isup2.hkl

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

C14H24N4O3	F000 = 640
Mr = 296.37	Dx = 1.215 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7693 reflections
a = 7.9318 (16) Å	θ = 2.6–25.0º
b = 6.6423 (13) Å	µ = 0.09 mm−1
c = 31.191 (7) Å	T = 293 (2) K
β = 99.55 (3)º	Block, colourless
V = 1620.5 (6) Å3	0.60 × 0.30 × 0.08 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2825 independent reflections
Radiation source: Fine-focus sealed tube	1306 reflections with I > 2σ(I)
Monochromator: Graphite	Rint = 0.051
Detector resolution: 10.00 pixels mm-1	θmax = 25.0º
T = 293(2) K	θmin = 1.3º
ω scans	h = 0→9
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	k = −7→0
Tmin = 0.943, Tmax = 0.993	l = −37→35
2825 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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.153	w = 1/[σ2(Fo2) + (0.0843P)2] where P = (Fo2 + 2Fc2)/3
S = 0.84	(Δ/σ)max = 0.014
2825 reflections	Δρmax = 0.28 e Å−3
194 parameters	Δρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: None

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O1	−0.0768 (3)	0.9179 (3)	0.82543 (8)	0.0604 (7)
O2	−0.2995 (3)	1.0170 (4)	0.85187 (8)	0.0670 (7)
O3	−0.1951 (2)	0.2689 (3)	0.74730 (7)	0.0512 (6)
N1	−0.2308 (3)	0.9002 (4)	0.82899 (8)	0.0459 (7)
N2	−0.3292 (3)	0.7617 (4)	0.80698 (8)	0.0453 (7)
N3	−0.1290 (3)	0.4939 (4)	0.80512 (8)	0.0414 (6)
N4	−0.3001 (3)	0.6021 (4)	0.74324 (8)	0.0392 (6)
C1	−0.2455 (3)	0.6227 (4)	0.78538 (9)	0.0362 (7)
C2	−0.0594 (4)	0.3511 (5)	0.77744 (10)	0.0472 (8)
H2a	0.0212	0.4183	0.7621	0.057*
H2b	0.0004	0.2445	0.7950	0.057*
C3	−0.2672 (4)	0.4183 (5)	0.71928 (10)	0.0501 (9)
H3a	−0.3739	0.3699	0.7027	0.060*
H3b	−0.1907	0.4502	0.6990	0.060*
C4	−0.4042 (4)	0.7564 (5)	0.71773 (10)	0.0560 (9)
H4a	−0.3882	0.7482	0.6879	0.084*
H4b	−0.3700	0.8871	0.7291	0.084*
H4c	−0.5225	0.7348	0.7195	0.084*
C5	−0.0734 (3)	0.4762 (5)	0.85230 (9)	0.0439 (8)
H5a	−0.1016	0.3433	0.8619	0.053*
H5b	−0.1332	0.5747	0.8672	0.053*
C6	0.1153 (4)	0.5098 (5)	0.86376 (10)	0.0474 (8)
H6	0.1567	0.6275	0.8532	0.057*
C7	0.2293 (4)	0.3932 (5)	0.88694 (10)	0.0499 (8)
C8	0.4169 (4)	0.4518 (6)	0.89472 (10)	0.0608 (10)
H8a	0.4835	0.3403	0.8864	0.073*
H8b	0.4328	0.5654	0.8763	0.073*
C9	0.4840 (4)	0.5072 (7)	0.94162 (11)	0.0740 (11)
H9a	0.4240	0.6254	0.9494	0.089*
H9b	0.4615	0.3976	0.9604	0.089*
C10	0.6736 (4)	0.5496 (6)	0.94863 (11)	0.0624 (10)
H10	0.7444	0.4383	0.9483	0.075*
C11	0.7505 (4)	0.7241 (6)	0.95516 (10)	0.0597 (9)
C12	0.9427 (5)	0.7390 (6)	0.96099 (13)	0.0838 (13)
H12a	0.9742	0.8405	0.9419	0.126*
H12b	0.9892	0.6117	0.9542	0.126*
H12c	0.9870	0.7744	0.9906	0.126*
C13	0.6634 (6)	0.9221 (6)	0.95783 (15)	0.0974 (14)
H13a	0.7091	0.9870	0.9848	0.146*
H13b	0.5430	0.9007	0.9565	0.146*
H13c	0.6824	1.0058	0.9340	0.146*
C14	0.1868 (5)	0.2002 (6)	0.90720 (13)	0.0861 (14)
H14a	0.2656	0.0975	0.9016	0.129*
H14b	0.0725	0.1605	0.8950	0.129*
H14c	0.1950	0.2183	0.9380	0.129*

	U11	U22	U33	U12	U13	U23
O1	0.0374 (12)	0.0485 (14)	0.0951 (18)	−0.0067 (11)	0.0103 (12)	−0.0033 (13)
O2	0.0714 (16)	0.0645 (16)	0.0645 (15)	0.0175 (13)	0.0094 (12)	−0.0191 (13)
O3	0.0433 (12)	0.0422 (12)	0.0677 (14)	−0.0059 (11)	0.0082 (11)	−0.0098 (12)
N1	0.0461 (17)	0.0434 (16)	0.0465 (16)	0.0077 (14)	0.0025 (13)	0.0017 (14)
N2	0.0296 (13)	0.0510 (16)	0.0534 (16)	0.0058 (13)	0.0011 (12)	−0.0096 (14)
N3	0.0336 (13)	0.0400 (14)	0.0478 (15)	0.0059 (12)	−0.0012 (11)	−0.0038 (13)
N4	0.0296 (12)	0.0432 (15)	0.0435 (15)	−0.0001 (11)	0.0027 (11)	−0.0017 (13)
C1	0.0183 (14)	0.0412 (18)	0.0479 (19)	−0.0034 (13)	0.0021 (13)	0.0002 (15)
C2	0.0379 (18)	0.0395 (18)	0.062 (2)	0.0052 (15)	0.0016 (15)	−0.0042 (17)
C3	0.0330 (17)	0.061 (2)	0.056 (2)	−0.0053 (16)	0.0070 (15)	−0.0113 (19)
C4	0.0399 (17)	0.074 (2)	0.0498 (19)	0.0089 (18)	−0.0048 (15)	0.0077 (18)
C5	0.0368 (16)	0.0465 (19)	0.0465 (18)	−0.0003 (15)	0.0014 (14)	0.0047 (16)
C6	0.0393 (17)	0.0513 (19)	0.0485 (18)	−0.0036 (16)	−0.0022 (14)	0.0069 (17)
C7	0.0458 (18)	0.056 (2)	0.0440 (18)	0.0006 (17)	−0.0053 (14)	−0.0021 (17)
C8	0.0424 (18)	0.082 (3)	0.053 (2)	0.0028 (18)	−0.0071 (16)	0.0019 (19)
C9	0.053 (2)	0.108 (3)	0.056 (2)	−0.015 (2)	−0.0043 (17)	−0.010 (2)
C10	0.046 (2)	0.072 (3)	0.065 (2)	−0.0023 (19)	−0.0049 (17)	−0.008 (2)
C11	0.057 (2)	0.066 (3)	0.053 (2)	0.000 (2)	−0.0002 (17)	−0.0038 (19)
C12	0.059 (2)	0.097 (3)	0.091 (3)	−0.022 (2)	0.002 (2)	−0.011 (3)
C13	0.100 (3)	0.084 (3)	0.105 (4)	0.010 (3)	0.008 (3)	−0.007 (3)
C14	0.078 (3)	0.067 (3)	0.097 (3)	−0.005 (2)	−0.032 (2)	0.027 (2)

O1—N1	1.251 (3)	C6—H6	0.9300
O2—N1	1.240 (3)	C7—C14	1.493 (5)
O3—C3	1.382 (3)	C7—C8	1.518 (4)
O3—C2	1.416 (3)	C8—C9	1.517 (4)
N1—N2	1.323 (3)	C8—H8a	0.9700
N2—C1	1.376 (3)	C8—H8b	0.9700
N3—C1	1.333 (3)	C9—C10	1.510 (4)
N3—C2	1.452 (4)	C9—H9a	0.9700
N3—C5	1.469 (4)	C9—H9b	0.9700
N4—C1	1.321 (3)	C10—C11	1.310 (5)
N4—C4	1.465 (4)	C10—H10	0.9300
N4—C3	1.477 (4)	C11—C13	1.494 (5)
C2—H2a	0.9700	C11—C12	1.508 (5)
C2—H2b	0.9700	C12—H12a	0.9600
C3—H3a	0.9700	C12—H12b	0.9600
C3—H3b	0.9700	C12—H12c	0.9600
C4—H4a	0.9600	C13—H13a	0.9600
C4—H4b	0.9600	C13—H13b	0.9600
C4—H4c	0.9600	C13—H13c	0.9600
C5—C6	1.496 (4)	C14—H14a	0.9600
C5—H5a	0.9700	C14—H14b	0.9600
C5—H5b	0.9700	C14—H14c	0.9600
C6—C7	1.313 (4)
C3—O3—C2	109.4 (2)	C5—C6—H6	116.1
O2—N1—O1	121.4 (3)	C6—C7—C14	123.8 (3)
O2—N1—N2	117.2 (3)	C6—C7—C8	120.3 (3)
O1—N1—N2	121.3 (3)	C14—C7—C8	115.9 (3)
N1—N2—C1	115.5 (2)	C9—C8—C7	113.2 (3)
C1—N3—C2	116.6 (2)	C9—C8—H8a	108.9
C1—N3—C5	125.7 (2)	C7—C8—H8a	108.9
C2—N3—C5	117.6 (2)	C9—C8—H8b	108.9
C1—N4—C4	122.0 (2)	C7—C8—H8b	108.9
C1—N4—C3	122.2 (2)	H8a—C8—H8b	107.8
C4—N4—C3	115.7 (2)	C10—C9—C8	111.5 (3)
N4—C1—N3	118.7 (3)	C10—C9—H9a	109.3
N4—C1—N2	116.8 (2)	C8—C9—H9a	109.3
N3—C1—N2	123.9 (3)	C10—C9—H9b	109.3
O3—C2—N3	108.9 (2)	C8—C9—H9b	109.3
O3—C2—H2a	109.9	H9a—C9—H9b	108.0
N3—C2—H2a	109.9	C11—C10—C9	127.9 (4)
O3—C2—H2b	109.9	C11—C10—H10	116.0
N3—C2—H2b	109.9	C9—C10—H10	116.0
H2a—C2—H2b	108.3	C10—C11—C13	125.4 (3)
O3—C3—N4	111.3 (2)	C10—C11—C12	120.8 (3)
O3—C3—H3a	109.4	C13—C11—C12	113.7 (3)
N4—C3—H3a	109.4	C11—C12—H12a	109.5
O3—C3—H3b	109.4	C11—C12—H12b	109.5
N4—C3—H3b	109.4	H12a—C12—H12b	109.5
H3a—C3—H3b	108.0	C11—C12—H12c	109.5
N4—C4—H4a	109.5	H12a—C12—H12c	109.5
N4—C4—H4b	109.5	H12b—C12—H12c	109.5
H4a—C4—H4b	109.5	C11—C13—H13a	109.5
N4—C4—H4c	109.5	C11—C13—H13b	109.5
H4a—C4—H4c	109.5	H13a—C13—H13b	109.5
H4b—C4—H4c	109.5	C11—C13—H13c	109.5
N3—C5—C6	110.5 (2)	H13a—C13—H13c	109.5
N3—C5—H5a	109.6	H13b—C13—H13c	109.5
C6—C5—H5a	109.6	C7—C14—H14a	109.5
N3—C5—H5b	109.6	C7—C14—H14b	109.5
C6—C5—H5b	109.6	H14a—C14—H14b	109.5
H5a—C5—H5b	108.1	C7—C14—H14c	109.5
C7—C6—C5	127.9 (3)	H14a—C14—H14c	109.5
C7—C6—H6	116.1	H14b—C14—H14c	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1i	0.97	2.48	3.257 (4)	136
C3—H3A···N2ii	0.97	2.43	3.336 (4)	155
C3—H3B···O1iii	0.97	2.38	3.264 (4)	151
C5—H5B···N1	0.97	2.53	3.117 (4)	119
C5—H5B···N2	0.97	2.55	2.960 (4)	105
C13—H13C···O2iv	0.96	2.59	3.425 (5)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O1i	0.97	2.48	3.257 (4)	136
C3—H3A⋯N2ii	0.97	2.43	3.336 (4)	155
C3—H3B⋯O1iii	0.97	2.38	3.264 (4)	151
C5—H5B⋯N1	0.97	2.53	3.117 (4)	119
C5—H5B⋯N2	0.97	2.55	2.960 (4)	105
C13—H13C⋯O2iv	0.96	2.59	3.425 (5)	145

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