1,5-Dimethyl-2-nitro­imino-1,3,5-tri­azinane

Zhao, C.; Yang, W.; Hu, Y.; Shen, L.; Lu, X.

doi:10.1107/S1600536808021533

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1515

doi:10.1107/S1600536808021533

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1,5-Dimethyl-2-nitroimino-1,3,5-triazinane

Cong Zhao,^a Wen-ge Yang,^a Yong-hong Hu,^a ^* Lei Shen ^a and Xiu-tao Lu ^a

^aCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: hyh@njut.edu.cn

(Received 9 July 2008; accepted 11 July 2008; online 16 July 2008)

The asymmetric unit of the title compound, C₅H₁₁N₅O₂, contains two independent molecules. The two triazine rings adopt envelope conformations. Intramolecular 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, intermolecular N—H⋯N, C—H⋯N and C—H⋯O hydrogen bonds link the molecules.

Related literature

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

Experimental

Crystal data

C₅H₁₁N₅O₂
M_r = 173.19
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.072
wR(F²) = 0.194
S = 1.00
2873 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.38 e Å⁻³

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⋯O4^iv	0.96	2.59	3.317 (6)	133
C8—H8B⋯O3ⁱⁱⁱ	0.97	2.56	3.420 (5)	148
C9—H9C⋯O1^v	0.97	2.59	3.359 (6)	137
Symmetry codes: (i) x-1, y, z-1; (ii) x+1, y, z+1; (iii) x, y, z+1; (iv) -x+1, -y, -z+1; (v) x-1, y, z.

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).

Supporting information

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

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

checkCIF report

Comment top

Nitroguanidine derivatives have a high insecticidal activity and a wide spectrum (Wakita et al., 2003). As part of our ongoing studies in this area, we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains two independent molecules, in which the bond lengths and angles are generally within normal ranges. Rings A (N1-N3/C3-C5) and B (N6-N8/C8-C10) have envelope conformations, with N3 and N6 atoms displaced by -0.652 (2) and -0.645 (3) Å, respectively, from the plane of the other rings atoms. The intramolecular C-H···N and N-H···O hydrogen bonds (Table 1) result in the formation of nearly planar two five- and two six-membered rings: C (N1/N4/C2/C3/H2B), D (O1/N2/N4/N5/C3/H2A) and E (N8/N9/C7/C10/H7B), F (O3/N7/N9/N10/C10/H7A). The dihedral angles between the rings are C/D = 1.63 (3)° and E/F = 3.43 (3)°. So, rings C, D and E, F are nearly coplanar.

In the crystal structure, intermolecular N-H···N, C-H···N and C-H···O hydrogen bonds (Table 1) link the molecules, in which they may be effective in the stabilization of the structure.

Related literature top

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

Experimental top

The title compound was synthesized according to the literature method (Shiokawa et al., 1991). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.

1,5-Dimethyl-2-nitroimino-1,3,5-triazinane top

Crystal data top

C₅H₁₁N₅O₂	F(000) = 736
M_r = 173.19	D_x = 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 = 9–12°
b = 30.103 (6) Å	µ = 0.11 mm⁻¹
c = 8.2940 (17) Å	T = 294 K
β = 104.19 (3)°	Block, colorless
V = 1609.4 (6) Å³	0.30 × 0.10 × 0.10 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	1979 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 25.2°, θ_min = 1.4°
ω/2θ scans	h = −7→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→36
T_min = 0.967, T_max = 0.989	l = 0→9
3126 measured reflections	3 standard reflections every 120 min
2873 independent reflections	intensity decay: none

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.194	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.06P)² + 4P] where P = (F_o² + 2F_c²)/3
2873 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₅H₁₁N₅O₂	V = 1609.4 (6) Å³
M_r = 173.19	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.6490 (13) Å	µ = 0.11 mm⁻¹
b = 30.103 (6) Å	T = 294 K
c = 8.2940 (17) Å	0.30 × 0.10 × 0.10 mm
β = 104.19 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1979 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.037
T_min = 0.967, T_max = 0.989	3 standard reflections every 120 min
3126 measured reflections	intensity decay: none
2873 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.194	H-atom parameters constrained
S = 1.00	Δρ_max = 0.36 e Å⁻³
2873 reflections	Δρ_min = −0.38 e Å⁻³
217 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O4^iv	0.96	2.59	3.317 (6)	133
C8—H8B···O3ⁱⁱⁱ	0.97	2.56	3.420 (5)	148
C9—H9C···O1^v	0.97	2.59	3.359 (6)	137

Symmetry codes: (i) x−1, y, z−1; (ii) x+1, y, z+1; (iii) x, y, z+1; (iv) −x+1, −y, −z+1; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₅H₁₁N₅O₂
M_r	173.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	6.6490 (13), 30.103 (6), 8.2940 (17)
β (°)	104.19 (3)
V (Å³)	1609.4 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.967, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	3126, 2873, 1979
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.194, 1.00
No. of reflections	2873
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.38

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.8600	1.9400	2.549 (5)	126.00
N7—H7A···O3	0.8600	1.9900	2.583 (5)	126.00
N7—H7A···N3ⁱ	0.8600	2.5700	3.210 (5)	132.00
C1—H1C···O3ⁱⁱ	0.9600	2.5400	3.309 (6)	137.00
C2—H2B···N4	0.9600	2.2400	2.699 (6)	108.00
C4—H4B···O4ⁱⁱⁱ	0.9700	2.5000	3.411 (6)	156.00
C4—H4C···O3ⁱⁱ	0.9700	2.4900	3.251 (6)	136.00
C7—H7B···N9	0.9600	2.2100	2.670 (5)	108.00
C7—H7B···O4^iv	0.9600	2.5900	3.317 (6)	133.00
C8—H8B···O3ⁱⁱⁱ	0.9700	2.5600	3.420 (5)	148.00
C9—H9C···O1^v	0.9700	2.5900	3.359 (6)	137.00

Symmetry codes: (i) x−1, y, z−1; (ii) x+1, y, z+1; (iii) x, y, z+1; (iv) −x+1, −y, −z+1; (v) x−1, y, z.

References

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shiokawa, K., Tsuboi, S., Moriya, K., Hattori, Y., Honda, I. & Shibuya, K. (1991). PCT Int. Appl. US 5032589. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wakita, T., Kinoshita, K., Yamada, E., Yasui, N., Kawahara, N., Naoi, A., Nakaya, M., Ebihara, K., Matsuno, H. & Kodaka, K. (2003). Pest Manag. Sci. 59, 1016–1022. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 64| Part 8| August 2008| Page o1515

doi:10.1107/S1600536808021533

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