1,5-Dimethyl-2-nitro-imino-1,3,5-tri-azinane.

The asymmetric unit of the title compound, C(5)H(11)N(5)O(2), contains two independent mol-ecules. The two triazine rings adopt envelope conformations. Intra-molecular C-H⋯N and N-H⋯O hydrogen bonds result in the formation of two five- and two six-membered rings which are nearly planar; in addition, they are also nearly coplanar. In the crystal structure, inter-molecular N-H⋯N, C-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For general background, see: Wakita et al. (2003 ▶). For related literature, see: Shiokawa et al. (1991 ▶).

Experimental

Crystal data

C5H11N5O2

M = 173.19

Monoclinic,

a = 6.6490 (13) Å

b = 30.103 (6) Å

c = 8.2940 (17) Å

β = 104.19 (3)°

V = 1609.4 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 294 (2) K

0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.967, T max = 0.989

3126 measured reflections

2873 independent reflections

1979 reflections with I > 2σ(I)

R int = 0.037

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.194

S = 1.00

2873 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021533/hk2491sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021533/hk2491Isup2.hkl

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

C5H11N5O2	F000 = 736
Mr = 173.19	Dx = 1.430 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 6.6490 (13) Å	θ = 9–12º
b = 30.103 (6) Å	µ = 0.11 mm−1
c = 8.2940 (17) Å	T = 294 (2) K
β = 104.19 (3)º	Block, colorless
V = 1609.4 (6) Å3	0.30 × 0.10 × 0.10 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	Rint = 0.037
Radiation source: fine-focus sealed tube	θmax = 25.2º
Monochromator: graphite	θmin = 1.4º
T = 294(2) K	h = −7→7
ω/2θ scans	k = 0→36
Absorption correction: ψ scan(North et al., 1968)	l = 0→9
Tmin = 0.967, Tmax = 0.989	3 standard reflections
3126 measured reflections	every 120 min
2873 independent reflections	intensity decay: none
1979 reflections with I > 2σ(I)

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)] = 0.072	H-atom parameters constrained
wR(F2) = 0.194	w = 1/[σ2(Fo2) + (0.06P)2 + 4P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2873 reflections	Δρmax = 0.36 e Å−3
217 parameters	Δρmin = −0.37 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2sigma(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	0.4157 (7)	0.16494 (15)	0.6298 (4)	0.0982 (15)
O2	0.2294 (5)	0.22215 (11)	0.5490 (4)	0.0699 (10)
N1	0.3763 (5)	0.19429 (11)	1.0927 (4)	0.0447 (8)
N2	0.4955 (5)	0.14315 (11)	0.9359 (4)	0.0466 (8)
H2A	0.5027	0.1334	0.8400	0.056*
N3	0.6537 (5)	0.14525 (12)	1.2299 (4)	0.0501 (9)
N4	0.3096 (5)	0.20872 (11)	0.8150 (4)	0.0469 (8)
N5	0.3202 (5)	0.19792 (13)	0.6628 (4)	0.0549 (10)
C1	0.8312 (7)	0.17403 (17)	1.2213 (7)	0.0731 (15)
H1A	0.8666	0.1925	1.3184	0.110*
H1B	0.7939	0.1924	1.1238	0.110*
H1C	0.9481	0.1559	1.2160	0.110*
C2	0.2708 (8)	0.23592 (15)	1.1160 (6)	0.0616 (12)
H2B	0.2130	0.2493	1.0097	0.092*
H2C	0.3688	0.2559	1.1835	0.092*
H2D	0.1617	0.2297	1.1701	0.092*
C3	0.3970 (6)	0.18117 (13)	0.9446 (5)	0.0442 (9)
C4	0.5922 (7)	0.11728 (14)	1.0841 (5)	0.0500 (10)
H4B	0.4951	0.0950	1.1029	0.060*
H4C	0.7132	0.1020	1.0657	0.060*
C5	0.4757 (8)	0.16943 (17)	1.2470 (5)	0.0621 (13)
H5A	0.5162	0.1902	1.3387	0.075*
H5B	0.3757	0.1489	1.2734	0.075*
O3	0.0455 (5)	0.07427 (13)	0.2450 (4)	0.0804 (12)
O4	0.3371 (5)	0.04202 (11)	0.2690 (4)	0.0640 (9)
N6	−0.1841 (5)	0.09106 (11)	0.7596 (4)	0.0466 (8)
N7	−0.1239 (4)	0.07164 (11)	0.4938 (4)	0.0421 (8)
H7A	−0.1508	0.0788	0.3904	0.051*
N8	0.0994 (5)	0.04358 (11)	0.7263 (4)	0.0429 (8)
N9	0.2160 (5)	0.04411 (11)	0.4922 (4)	0.0424 (8)
N10	0.1942 (5)	0.05374 (11)	0.3332 (4)	0.0426 (8)
C6	−0.0729 (8)	0.13372 (16)	0.7715 (7)	0.0729 (15)
H6A	−0.0136	0.1407	0.8863	0.109*
H6B	−0.1680	0.1567	0.7221	0.109*
H6C	0.0355	0.1316	0.7138	0.109*
C7	0.2916 (7)	0.02129 (16)	0.8125 (5)	0.0579 (12)
H7B	0.3745	0.0154	0.7351	0.087*
H7C	0.2587	−0.0062	0.8589	0.087*
H7D	0.3674	0.0401	0.9001	0.087*
C8	−0.0443 (6)	0.05545 (15)	0.8268 (5)	0.0486 (10)
H8A	−0.1253	0.0294	0.8391	0.058*
H8B	0.0352	0.0639	0.9369	0.058*
C9	−0.2774 (6)	0.07940 (15)	0.5863 (5)	0.0481 (10)
H9B	−0.3612	0.0529	0.5830	0.058*
H9C	−0.3682	0.1033	0.5342	0.058*
C10	0.0585 (5)	0.05359 (12)	0.5651 (4)	0.0371 (8)

	U11	U22	U33	U12	U13	U23
O1	0.131 (3)	0.121 (3)	0.0415 (19)	0.080 (3)	0.019 (2)	0.023 (2)
O2	0.085 (2)	0.070 (2)	0.0385 (16)	0.0103 (18)	−0.0163 (15)	0.0154 (15)
N1	0.0489 (19)	0.050 (2)	0.0296 (16)	0.0062 (15)	−0.0016 (14)	0.0029 (14)
N2	0.053 (2)	0.050 (2)	0.0286 (16)	0.0079 (16)	−0.0075 (14)	0.0035 (14)
N3	0.054 (2)	0.054 (2)	0.0308 (17)	0.0081 (17)	−0.0110 (14)	0.0006 (15)
N4	0.050 (2)	0.051 (2)	0.0281 (17)	−0.0018 (16)	−0.0123 (14)	0.0093 (14)
N5	0.049 (2)	0.059 (2)	0.043 (2)	0.0020 (18)	−0.0152 (16)	0.0148 (18)
C1	0.056 (3)	0.058 (3)	0.082 (4)	−0.009 (2)	−0.026 (3)	−0.001 (3)
C2	0.068 (3)	0.058 (3)	0.055 (3)	0.011 (2)	0.007 (2)	0.002 (2)
C3	0.039 (2)	0.043 (2)	0.039 (2)	−0.0049 (17)	−0.0137 (16)	0.0054 (17)
C4	0.059 (3)	0.044 (2)	0.036 (2)	−0.0027 (19)	−0.0087 (18)	0.0081 (18)
C5	0.075 (3)	0.070 (3)	0.033 (2)	0.017 (3)	−0.004 (2)	0.010 (2)
O3	0.080 (2)	0.117 (3)	0.0414 (17)	0.052 (2)	0.0087 (16)	0.0229 (18)
O4	0.0575 (19)	0.079 (2)	0.0566 (19)	0.0107 (17)	0.0153 (15)	0.0055 (16)
N6	0.0420 (18)	0.051 (2)	0.0409 (18)	−0.0008 (15)	−0.0012 (14)	−0.0055 (16)
N7	0.0349 (17)	0.059 (2)	0.0275 (16)	0.0067 (15)	−0.0026 (13)	0.0045 (14)
N8	0.0411 (18)	0.053 (2)	0.0274 (16)	0.0113 (15)	−0.0043 (13)	0.0025 (14)
N9	0.0380 (17)	0.050 (2)	0.0326 (17)	0.0027 (14)	−0.0036 (13)	0.0066 (14)
N10	0.0430 (18)	0.045 (2)	0.0373 (17)	0.0064 (15)	0.0054 (14)	0.0010 (14)
C6	0.065 (3)	0.057 (3)	0.094 (4)	−0.012 (2)	0.015 (3)	−0.022 (3)
C7	0.054 (3)	0.072 (3)	0.038 (2)	0.016 (2)	−0.0067 (19)	0.012 (2)
C8	0.050 (2)	0.061 (3)	0.031 (2)	0.001 (2)	0.0023 (17)	0.0038 (18)
C9	0.036 (2)	0.064 (3)	0.040 (2)	0.0028 (19)	0.0014 (16)	0.0006 (19)
C10	0.0341 (19)	0.035 (2)	0.0353 (19)	−0.0013 (15)	−0.0040 (15)	−0.0016 (15)

O1—N5	1.245 (5)	O3—N10	1.241 (4)
O2—N5	1.228 (4)	O4—N10	1.249 (4)
N1—C3	1.329 (5)	N6—C8	1.439 (5)
N1—C2	1.472 (5)	N6—C9	1.461 (5)
N1—C5	1.490 (5)	N6—C6	1.473 (6)
N2—C3	1.329 (5)	N7—C10	1.328 (4)
N2—C4	1.464 (5)	N7—C9	1.438 (5)
N2—H2A	0.8600	N7—H7A	0.8600
N3—C5	1.426 (6)	N8—C10	1.332 (5)
N3—C4	1.448 (5)	N8—C8	1.458 (5)
N3—C1	1.480 (6)	N8—C7	1.465 (5)
N4—N5	1.322 (5)	N9—N10	1.323 (4)
N4—C3	1.369 (5)	N9—C10	1.362 (5)
C1—H1A	0.9600	C6—H6A	0.9600
C1—H1B	0.9600	C6—H6B	0.9600
C1—H1C	0.9600	C6—H6C	0.9600
C2—H2B	0.9600	C7—H7B	0.9600
C2—H2C	0.9600	C7—H7C	0.9600
C2—H2D	0.9600	C7—H7D	0.9600
C4—H4B	0.9700	C8—H8A	0.9700
C4—H4C	0.9700	C8—H8B	0.9700
C5—H5A	0.9700	C9—H9B	0.9700
C5—H5B	0.9700	C9—H9C	0.9700
C3—N1—C2	122.4 (3)	C8—N6—C9	106.3 (3)
C3—N1—C5	121.3 (3)	C8—N6—C6	110.9 (3)
C2—N1—C5	116.1 (3)	C9—N6—C6	111.1 (4)
C3—N2—C4	122.3 (3)	C10—N7—C9	121.2 (3)
C3—N2—H2A	118.9	C10—N7—H7A	119.4
C4—N2—H2A	118.9	C9—N7—H7A	119.4
C5—N3—C4	108.0 (3)	C10—N8—C8	121.2 (3)
C5—N3—C1	113.4 (4)	C10—N8—C7	122.2 (3)
C4—N3—C1	111.4 (4)	C8—N8—C7	116.6 (3)
N5—N4—C3	119.3 (4)	N10—N9—C10	119.2 (3)
O2—N5—O1	119.1 (4)	O3—N10—O4	118.0 (3)
O2—N5—N4	117.2 (4)	O3—N10—N9	125.0 (3)
O1—N5—N4	123.7 (3)	O4—N10—N9	117.0 (3)
N3—C1—H1A	109.5	N6—C6—H6A	109.5
N3—C1—H1B	109.5	N6—C6—H6B	109.5
H1A—C1—H1B	109.5	H6A—C6—H6B	109.5
N3—C1—H1C	109.5	N6—C6—H6C	109.5
H1A—C1—H1C	109.5	H6A—C6—H6C	109.5
H1B—C1—H1C	109.5	H6B—C6—H6C	109.5
N1—C2—H2B	109.5	N8—C7—H7B	109.5
N1—C2—H2C	109.5	N8—C7—H7C	109.5
H2B—C2—H2C	109.5	H7B—C7—H7C	109.5
N1—C2—H2D	109.5	N8—C7—H7D	109.5
H2B—C2—H2D	109.5	H7B—C7—H7D	109.5
H2C—C2—H2D	109.5	H7C—C7—H7D	109.5
N1—C3—N2	118.0 (3)	N6—C8—N8	114.4 (3)
N1—C3—N4	115.2 (4)	N6—C8—H8A	108.7
N2—C3—N4	126.8 (4)	N8—C8—H8A	108.7
N3—C4—N2	111.6 (3)	N6—C8—H8B	108.7
N3—C4—H4B	109.3	N8—C8—H8B	108.7
N2—C4—H4B	109.3	H8A—C8—H8B	107.6
N3—C4—H4C	109.3	N7—C9—N6	112.2 (3)
N2—C4—H4C	109.3	N7—C9—H9B	109.2
H4B—C4—H4C	108.0	N6—C9—H9B	109.2
N3—C5—N1	112.0 (4)	N7—C9—H9C	109.2
N3—C5—H5A	109.2	N6—C9—H9C	109.2
N1—C5—H5A	109.2	H9B—C9—H9C	107.9
N3—C5—H5B	109.2	N7—C10—N8	118.6 (3)
N1—C5—H5B	109.2	N7—C10—N9	127.3 (3)
H5A—C5—H5B	107.9	N8—C10—N9	114.1 (3)
C3—N4—N5—O2	175.8 (4)	C10—N9—N10—O3	5.9 (6)
C3—N4—N5—O1	−4.1 (6)	C10—N9—N10—O4	−175.7 (3)
C2—N1—C3—N2	179.7 (4)	C9—N6—C8—N8	50.4 (4)
C5—N1—C3—N2	5.2 (6)	C6—N6—C8—N8	−70.5 (5)
C2—N1—C3—N4	−1.2 (6)	C10—N8—C8—N6	−21.6 (5)
C5—N1—C3—N4	−175.7 (4)	C7—N8—C8—N6	156.9 (4)
C4—N2—C3—N1	−4.1 (6)	C10—N7—C9—N6	33.9 (5)
C4—N2—C3—N4	176.9 (4)	C8—N6—C9—N7	−56.1 (4)
N5—N4—C3—N1	−179.0 (3)	C6—N6—C9—N7	64.7 (5)
N5—N4—C3—N2	0.0 (6)	C9—N7—C10—N8	−1.5 (5)
C5—N3—C4—N2	55.1 (5)	C9—N7—C10—N9	179.4 (4)
C1—N3—C4—N2	−70.1 (4)	C8—N8—C10—N7	−5.1 (5)
C3—N2—C4—N3	−27.1 (5)	C7—N8—C10—N7	176.4 (4)
C4—N3—C5—N1	−54.2 (5)	C8—N8—C10—N9	174.1 (3)
C1—N3—C5—N1	69.8 (5)	C7—N8—C10—N9	−4.3 (5)
C3—N1—C5—N3	25.4 (6)	N10—N9—C10—N7	0.9 (6)
C2—N1—C5—N3	−149.4 (4)	N10—N9—C10—N8	−178.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.94	2.549 (5)	126
N7—H7A···O3	0.86	1.99	2.583 (5)	126
N7—H7A···N3i	0.86	2.57	3.210 (5)	132
C1—H1C···O3ii	0.96	2.54	3.309 (6)	137
C2—H2B···N4	0.96	2.24	2.699 (6)	108
C4—H4B···O4iii	0.97	2.50	3.411 (6)	156
C4—H4C···O3ii	0.97	2.49	3.251 (6)	136
C7—H7B···N9	0.96	2.21	2.670 (5)	108
C7—H7B···O4iv	0.96	2.59	3.317 (6)	133
C8—H8B···O3iii	0.97	2.56	3.420 (5)	148
C9—H9C···O1v	0.97	2.59	3.359 (6)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.94	2.549 (5)	126
N7—H7A⋯O3	0.86	1.99	2.583 (5)	126
N7—H7A⋯N3i	0.86	2.57	3.210 (5)	132
C1—H1C⋯O3ii	0.96	2.54	3.309 (6)	137
C2—H2B⋯N4	0.96	2.24	2.699 (6)	108
C4—H4B⋯O4iii	0.97	2.50	3.411 (6)	156
C4—H4C⋯O3ii	0.97	2.49	3.251 (6)	136
C7—H7B⋯N9	0.96	2.21	2.670 (5)	108
C7—H7B⋯O4iv	0.96	2.59	3.317 (6)	133
C8—H8B⋯O3iii	0.97	2.56	3.420 (5)	148
C9—H9C⋯O1v	0.97	2.59	3.359 (6)	137

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