(E)-5-Benzyl-1-methyl-N-nitro-1,3,5-triazinan-2-imine.

In the title compound, C(11)H(15)N(5)O(2), the 1,3,5-triazine ring exhibits a half-chair conformation. An intra-molecular N-H⋯O inter-action occurs. In the crystal structure, mol-ecules are connected by inter-molecular C-H⋯O and N-H⋯N hydrogen bonds, forming a zigzag chain along the b axis.

Related literature

For the synthesis of the title compound, see: Ebihara et al. (1998 ▶). For related structures, see: Hu et al. (2008 ▶); Zhao et al. (2008 ▶).

Experimental

Crystal data

C11H15N5O2

M = 249.28

Monoclinic,

a = 12.293 (3) Å

b = 6.7769 (14) Å

c = 14.858 (3) Å

β = 107.36 (3)°

V = 1181.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.45 × 0.13 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.956, T max = 0.990

10812 measured reflections

2697 independent reflections

2215 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.141

S = 1.15

2697 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.28 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009426/is2529sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009426/is2529Isup2.hkl

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

C11H15N5O2	F(000) = 528
Mr = 249.28	Dx = 1.401 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2501 reflections
a = 12.293 (3) Å	θ = 2.3–25.1°
b = 6.7769 (14) Å	µ = 0.10 mm−1
c = 14.858 (3) Å	T = 293 K
β = 107.36 (3)°	Needle, colorless
V = 1181.5 (4) Å3	0.45 × 0.13 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID IP area-detector diffractometer	2697 independent reflections
Radiation source: Rotating Anode	2215 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −15→15
Tmin = 0.956, Tmax = 0.990	k = −8→8
10812 measured reflections	l = −19→19

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0641P)2 + 0.4408P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
2697 reflections	Δρmax = 0.33 e Å−3
164 parameters	Δρmin = −0.28 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: 0.053 (5)

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
O1	−0.08476 (12)	0.2664 (2)	0.32912 (13)	0.0648 (5)
O2	−0.20472 (10)	0.4688 (2)	0.23990 (9)	0.0491 (4)
N1	0.13187 (12)	0.3877 (2)	0.34487 (10)	0.0396 (4)
H1A	0.0946	0.2966	0.3081	0.048*
N2	0.13204 (11)	0.69132 (19)	0.41305 (9)	0.0337 (3)
N3	0.29652 (11)	0.4822 (2)	0.47169 (9)	0.0324 (3)
N4	−0.03718 (11)	0.5836 (2)	0.31457 (11)	0.0399 (4)
N5	−0.10875 (11)	0.4321 (2)	0.29433 (9)	0.0342 (3)
C1	0.07548 (13)	0.5462 (2)	0.35840 (10)	0.0320 (3)
C2	0.07568 (15)	0.8650 (3)	0.43518 (14)	0.0446 (4)
H2A	−0.0053	0.8513	0.4084	0.067*
H2B	0.1011	0.9799	0.4094	0.067*
H2C	0.0940	0.8786	0.5024	0.067*
C3	0.25803 (13)	0.6801 (2)	0.44754 (12)	0.0379 (4)
H3A	0.2893	0.7288	0.3991	0.046*
H3B	0.2858	0.7639	0.5025	0.046*
C4	0.25463 (13)	0.3596 (3)	0.38930 (11)	0.0354 (4)
H4B	0.2694	0.2222	0.4071	0.043*
H4C	0.2951	0.3913	0.3443	0.043*
C5	0.26964 (14)	0.4064 (3)	0.55497 (11)	0.0370 (4)
H5A	0.1889	0.3765	0.5381	0.044*
H5B	0.2855	0.5083	0.6030	0.044*
C6	0.33636 (12)	0.2241 (2)	0.59520 (10)	0.0305 (3)
C7	0.29232 (14)	0.0894 (3)	0.64553 (11)	0.0366 (4)
H7A	0.2200	0.1099	0.6516	0.044*
C8	0.35422 (16)	−0.0750 (3)	0.68681 (12)	0.0420 (4)
H8A	0.3239	−0.1632	0.7209	0.050*
C9	0.46112 (16)	−0.1076 (3)	0.67726 (12)	0.0426 (4)
H9A	0.5029	−0.2181	0.7046	0.051*
C10	0.50547 (14)	0.0239 (3)	0.62723 (12)	0.0426 (4)
H10A	0.5775	0.0018	0.6209	0.051*
C11	0.44426 (13)	0.1892 (3)	0.58611 (11)	0.0376 (4)
H11A	0.4753	0.2770	0.5524	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0479 (8)	0.0396 (8)	0.1065 (13)	−0.0004 (6)	0.0227 (8)	0.0232 (8)
O2	0.0311 (6)	0.0622 (9)	0.0465 (7)	−0.0060 (6)	0.0002 (5)	−0.0005 (6)
N1	0.0354 (7)	0.0328 (7)	0.0410 (8)	0.0066 (6)	−0.0033 (6)	−0.0094 (6)
N2	0.0310 (7)	0.0272 (7)	0.0375 (7)	0.0028 (5)	0.0022 (5)	−0.0029 (5)
N3	0.0301 (6)	0.0355 (7)	0.0283 (6)	0.0030 (5)	0.0038 (5)	0.0022 (5)
N4	0.0302 (7)	0.0320 (7)	0.0485 (8)	−0.0010 (6)	−0.0020 (6)	0.0041 (6)
N5	0.0324 (7)	0.0367 (7)	0.0341 (7)	−0.0014 (6)	0.0106 (5)	0.0000 (5)
C1	0.0325 (7)	0.0290 (7)	0.0297 (7)	0.0025 (6)	0.0019 (6)	0.0016 (6)
C2	0.0442 (9)	0.0344 (9)	0.0510 (10)	0.0073 (7)	0.0079 (8)	−0.0097 (7)
C3	0.0306 (8)	0.0341 (8)	0.0423 (9)	−0.0016 (6)	0.0005 (6)	0.0018 (7)
C4	0.0336 (8)	0.0413 (9)	0.0296 (7)	0.0088 (7)	0.0065 (6)	−0.0003 (6)
C5	0.0372 (8)	0.0441 (9)	0.0301 (8)	0.0096 (7)	0.0105 (6)	0.0018 (7)
C6	0.0297 (7)	0.0363 (8)	0.0231 (6)	0.0011 (6)	0.0042 (5)	−0.0020 (6)
C7	0.0329 (7)	0.0467 (9)	0.0296 (7)	−0.0024 (7)	0.0086 (6)	−0.0020 (7)
C8	0.0502 (10)	0.0419 (9)	0.0324 (8)	−0.0064 (8)	0.0101 (7)	0.0030 (7)
C9	0.0486 (10)	0.0378 (9)	0.0346 (8)	0.0066 (8)	0.0021 (7)	0.0045 (7)
C10	0.0339 (8)	0.0483 (10)	0.0442 (9)	0.0103 (7)	0.0094 (7)	0.0042 (8)
C11	0.0326 (8)	0.0449 (9)	0.0357 (8)	0.0022 (7)	0.0109 (6)	0.0071 (7)

O1—N5	1.2350 (19)	C3—H3B	0.9700
O2—N5	1.2404 (18)	C4—H4B	0.9700
N1—C1	1.326 (2)	C4—H4C	0.9700
N1—C4	1.468 (2)	C5—C6	1.505 (2)
N1—H1A	0.8600	C5—H5A	0.9700
N2—C1	1.332 (2)	C5—H5B	0.9700
N2—C2	1.452 (2)	C6—C7	1.388 (2)
N2—C3	1.4811 (19)	C6—C11	1.393 (2)
N3—C3	1.431 (2)	C7—C8	1.385 (2)
N3—C4	1.442 (2)	C7—H7A	0.9300
N3—C5	1.466 (2)	C8—C9	1.381 (3)
N4—N5	1.3269 (19)	C8—H8A	0.9300
N4—C1	1.367 (2)	C9—C10	1.373 (3)
C2—H2A	0.9600	C9—H9A	0.9300
C2—H2B	0.9600	C10—C11	1.385 (2)
C2—H2C	0.9600	C10—H10A	0.9300
C3—H3A	0.9700	C11—H11A	0.9300
C1—N1—C4	123.43 (14)	N3—C4—H4B	109.3
C1—N1—H1A	118.3	N1—C4—H4B	109.3
C4—N1—H1A	118.3	N3—C4—H4C	109.3
C1—N2—C2	122.62 (13)	N1—C4—H4C	109.3
C1—N2—C3	118.34 (13)	H4B—C4—H4C	108.0
C2—N2—C3	118.93 (13)	N3—C5—C6	112.94 (12)
C3—N3—C4	108.64 (12)	N3—C5—H5A	109.0
C3—N3—C5	113.51 (13)	C6—C5—H5A	109.0
C4—N3—C5	113.66 (14)	N3—C5—H5B	109.0
N5—N4—C1	118.25 (13)	C6—C5—H5B	109.0
O1—N5—O2	121.13 (14)	H5A—C5—H5B	107.8
O1—N5—N4	123.34 (14)	C7—C6—C11	118.43 (15)
O2—N5—N4	115.48 (14)	C7—C6—C5	120.00 (14)
N1—C1—N2	119.30 (14)	C11—C6—C5	121.53 (14)
N1—C1—N4	125.42 (14)	C8—C7—C6	121.10 (15)
N2—C1—N4	115.07 (14)	C8—C7—H7A	119.5
N2—C2—H2A	109.5	C6—C7—H7A	119.5
N2—C2—H2B	109.5	C9—C8—C7	119.81 (16)
H2A—C2—H2B	109.5	C9—C8—H8A	120.1
N2—C2—H2C	109.5	C7—C8—H8A	120.1
H2A—C2—H2C	109.5	C10—C9—C8	119.68 (16)
H2B—C2—H2C	109.5	C10—C9—H9A	120.2
N3—C3—N2	111.61 (13)	C8—C9—H9A	120.2
N3—C3—H3A	109.3	C9—C10—C11	120.81 (16)
N2—C3—H3A	109.3	C9—C10—H10A	119.6
N3—C3—H3B	109.3	C11—C10—H10A	119.6
N2—C3—H3B	109.3	C10—C11—C6	120.15 (15)
H3A—C3—H3B	108.0	C10—C11—H11A	119.9
N3—C4—N1	111.46 (13)	C6—C11—H11A	119.9
C1—N4—N5—O1	15.3 (2)	C5—N3—C4—N1	77.68 (17)
C1—N4—N5—O2	−167.27 (14)	C1—N1—C4—N3	20.6 (2)
C4—N1—C1—N2	1.7 (2)	C3—N3—C5—C6	−164.43 (13)
C4—N1—C1—N4	176.15 (15)	C4—N3—C5—C6	70.73 (17)
C2—N2—C1—N1	−176.81 (16)	N3—C5—C6—C7	−153.33 (14)
C3—N2—C1—N1	7.1 (2)	N3—C5—C6—C11	28.9 (2)
C2—N2—C1—N4	8.2 (2)	C11—C6—C7—C8	0.7 (2)
C3—N2—C1—N4	−167.92 (14)	C5—C6—C7—C8	−177.09 (14)
N5—N4—C1—N1	34.1 (2)	C6—C7—C8—C9	−0.7 (3)
N5—N4—C1—N2	−151.22 (15)	C7—C8—C9—C10	0.3 (3)
C4—N3—C3—N2	59.01 (17)	C8—C9—C10—C11	0.0 (3)
C5—N3—C3—N2	−68.49 (17)	C9—C10—C11—C6	0.1 (3)
C1—N2—C3—N3	−38.5 (2)	C7—C6—C11—C10	−0.4 (2)
C2—N2—C3—N3	145.25 (15)	C5—C6—C11—C10	177.37 (15)
C3—N3—C4—N1	−49.73 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4i	0.86	2.27	3.093 (2)	162
C3—H3A···O2ii	0.97	2.59	3.305 (2)	131
N1—H1A···O1	0.86	2.33	2.730 (2)	109

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N4i	0.86	2.27	3.093 (2)	162
C3—H3A⋯O2ii	0.97	2.59	3.305 (2)	131
N1—H1A⋯O1	0.86	2.33	2.730 (2)	109

Symmetry codes: (i) ; (ii) .