Crystal structure of pymetrozine.

The title compound, C10H11N5O {systematic name: 6-methyl-4-[(E)-(pyridin-3-yl-methyl-idene)amino]-4,5-di-hydro-1,2,4-triazin-3(2H)-one}, C10H11N5O, is used as an anti-feedant in pest control. The asymmetric unit comprises two independent mol-ecules, A and B, in which the dihedral angles between the pyridinyl and triazinyl ring planes [r.m.s. deviations = 0.0132 and 0.0255 ] are 11.60 (6) and 18.06 (4)°, respectively. In the crystal, N-H⋯O, N-H⋯N, C-H⋯N and C-H⋯O hydrogen bonds, together with weak π-π inter-actions [ring-centroid separations = 3.5456 (9) and 3.9142 (9) Å], link the pyridinyl and triazinyl rings of A mol-ecules, generating a three-dimensional network.

Related literature

For information on the toxicity and insecticidal properties of the title compound, see: He et al. (2011 ▸); Torres et al. (2003 ▸); Ausborn et al. (2005 ▸); Barati et al. (2013 ▸). For a related crystal structure, see: Wang et al. (2012 ▸).

Experimental

Crystal data

C10H11N5O

M = 217.24

Monoclinic,

a = 8.0803 (2) Å

b = 23.7497 (6) Å

c = 10.7846 (3) Å

β = 98.962 (1)°

V = 2044.35 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.37 × 0.16 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.964, T max = 0.991

19037 measured reflections

3987 independent reflections

3103 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.04

3987 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2010 ▸); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015010804/sj5463sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015010804/sj5463Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015010804/sj5463Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015010804/sj5463fig1.tif

The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Click here for additional data file.

a . DOI: 10.1107/S2056989015010804/sj5463fig2.tif

Crystal packing viewed along the a axis. The hydrogen bonds are shown as dashed lines.

CCDC reference: 1404941

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H11N5O	F(000) = 912
Mr = 217.24	Dx = 1.412 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.0803 (2) Å	Cell parameters from 3981 reflections
b = 23.7497 (6) Å	θ = 2.7–27.3°
c = 10.7846 (3) Å	µ = 0.10 mm−1
β = 98.962 (1)°	T = 173 K
V = 2044.35 (9) Å3	Block, colourless
Z = 8	0.37 × 0.16 × 0.09 mm

Bruker APEXII CCD diffractometer	3987 independent reflections
Radiation source: fine-focus sealed tube	3103 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→9
Tmin = 0.964, Tmax = 0.991	k = −28→29
19037 measured reflections	l = −13→12

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) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0528P)2 + 0.3325P] where P = (Fo2 + 2Fc2)/3
3987 reflections	(Δ/σ)max = 0.001
291 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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 > 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	0.54588 (13)	0.37396 (4)	0.67454 (12)	0.0371 (3)
O2	0.65704 (12)	0.09515 (4)	−0.11461 (10)	0.0298 (3)
N1	1.18740 (16)	0.17122 (6)	0.90565 (15)	0.0353 (4)
N2	0.70889 (14)	0.27719 (5)	0.72493 (13)	0.0269 (3)
N3	0.54303 (15)	0.27730 (5)	0.67218 (13)	0.0272 (3)
N4	0.31072 (15)	0.32889 (5)	0.58809 (14)	0.0333 (3)
H4	0.2610	0.3618	0.5750	0.040*
N5	0.21533 (15)	0.28219 (5)	0.54719 (14)	0.0314 (3)
N6	0.56087 (18)	0.08007 (6)	0.54024 (13)	0.0362 (3)
N7	0.53681 (14)	0.07233 (5)	0.09543 (12)	0.0226 (3)
N8	0.43763 (14)	0.06556 (5)	−0.01909 (12)	0.0212 (3)
N9	0.41093 (15)	0.07374 (5)	−0.23457 (12)	0.0273 (3)
H9	0.4531	0.0850	−0.3008	0.033*
N10	0.24931 (16)	0.05238 (5)	−0.25699 (13)	0.0266 (3)
C1	1.28109 (19)	0.21759 (7)	0.91859 (17)	0.0325 (4)
H1	1.3940	0.2145	0.9587	0.039*
C2	1.22268 (19)	0.26979 (7)	0.87674 (17)	0.0346 (4)
H2	1.2949	0.3016	0.8865	0.041*
C3	1.05822 (19)	0.27537 (6)	0.82046 (17)	0.0319 (4)
H3	1.0158	0.3109	0.7900	0.038*
C4	0.95585 (18)	0.22816 (6)	0.80914 (15)	0.0253 (3)
C5	1.02808 (19)	0.17746 (6)	0.85192 (16)	0.0305 (4)
H5	0.9594	0.1448	0.8423	0.037*
C6	0.77874 (18)	0.22966 (6)	0.75433 (16)	0.0269 (4)
H6	0.7162	0.1958	0.7407	0.032*
C7	0.47257 (18)	0.32978 (6)	0.64618 (16)	0.0275 (4)
C8	0.28134 (18)	0.23414 (7)	0.57182 (16)	0.0281 (4)
C9	0.45481 (18)	0.22477 (6)	0.63922 (16)	0.0274 (4)
H9A	0.4495	0.2029	0.7167	0.033*
H9B	0.5183	0.2022	0.5853	0.033*
C10	0.1823 (2)	0.18265 (7)	0.53033 (19)	0.0397 (5)
H10A	0.0639	0.1927	0.5073	0.060*
H10B	0.1946	0.1552	0.5989	0.060*
H10C	0.2234	0.1663	0.4575	0.060*
C11	0.7273 (2)	0.08409 (7)	0.55839 (17)	0.0368 (4)
H11	0.7839	0.0886	0.6418	0.044*
C12	0.8219 (2)	0.08200 (7)	0.46212 (17)	0.0340 (4)
H12	0.9406	0.0842	0.4797	0.041*
C13	0.74117 (19)	0.07667 (6)	0.34017 (16)	0.0283 (4)
H13	0.8032	0.0761	0.2722	0.034*
C14	0.56786 (18)	0.07210 (6)	0.31837 (15)	0.0247 (3)
C15	0.4844 (2)	0.07337 (7)	0.42216 (16)	0.0315 (4)
H15	0.3661	0.0692	0.4080	0.038*
C16	0.46794 (19)	0.06629 (6)	0.19390 (15)	0.0250 (3)
H16	0.3517	0.0580	0.1860	0.030*
C17	0.51141 (17)	0.07926 (6)	−0.12215 (14)	0.0219 (3)
C18	0.18317 (18)	0.03964 (6)	−0.16097 (15)	0.0241 (3)
C19	0.26507 (17)	0.04665 (6)	−0.02804 (15)	0.0233 (3)
H19A	0.2010	0.0744	0.0140	0.028*
H19B	0.2626	0.0103	0.0164	0.028*
C20	0.01097 (18)	0.01533 (7)	−0.17992 (17)	0.0324 (4)
H20A	−0.0309	0.0125	−0.2700	0.049*
H20B	−0.0633	0.0397	−0.1402	0.049*
H20C	0.0140	−0.0222	−0.1420	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0312 (6)	0.0260 (6)	0.0533 (9)	0.0021 (5)	0.0041 (5)	−0.0001 (6)
O2	0.0280 (6)	0.0374 (6)	0.0254 (7)	−0.0084 (4)	0.0079 (5)	−0.0027 (5)
N1	0.0292 (7)	0.0321 (7)	0.0420 (10)	0.0044 (6)	−0.0023 (6)	0.0034 (7)
N2	0.0211 (7)	0.0294 (7)	0.0295 (8)	0.0016 (5)	0.0015 (5)	0.0001 (6)
N3	0.0219 (6)	0.0254 (7)	0.0327 (8)	0.0026 (5)	−0.0004 (6)	0.0018 (6)
N4	0.0254 (7)	0.0264 (7)	0.0465 (10)	0.0062 (5)	0.0010 (6)	0.0034 (7)
N5	0.0243 (7)	0.0336 (7)	0.0354 (9)	0.0011 (5)	0.0024 (6)	0.0027 (6)
N6	0.0471 (9)	0.0417 (8)	0.0204 (8)	−0.0003 (6)	0.0073 (6)	−0.0018 (7)
N7	0.0266 (7)	0.0222 (6)	0.0185 (7)	−0.0007 (5)	0.0024 (5)	−0.0007 (6)
N8	0.0214 (6)	0.0250 (6)	0.0170 (7)	−0.0028 (5)	0.0029 (5)	0.0000 (5)
N9	0.0299 (7)	0.0342 (7)	0.0182 (7)	−0.0078 (5)	0.0045 (5)	0.0019 (6)
N10	0.0275 (7)	0.0257 (7)	0.0256 (8)	−0.0025 (5)	0.0004 (6)	−0.0010 (6)
C1	0.0243 (8)	0.0389 (9)	0.0330 (10)	0.0029 (7)	0.0007 (7)	−0.0018 (8)
C2	0.0274 (8)	0.0322 (9)	0.0431 (12)	−0.0046 (6)	0.0024 (7)	−0.0014 (8)
C3	0.0310 (9)	0.0248 (8)	0.0392 (11)	0.0023 (6)	0.0031 (7)	0.0020 (8)
C4	0.0252 (8)	0.0270 (8)	0.0236 (9)	0.0028 (6)	0.0037 (6)	−0.0019 (7)
C5	0.0291 (8)	0.0256 (8)	0.0352 (10)	−0.0008 (6)	0.0002 (7)	−0.0008 (7)
C6	0.0260 (8)	0.0264 (8)	0.0278 (9)	0.0006 (6)	0.0031 (7)	−0.0001 (7)
C7	0.0257 (8)	0.0265 (8)	0.0313 (10)	0.0039 (6)	0.0080 (7)	0.0031 (7)
C8	0.0246 (8)	0.0332 (8)	0.0267 (9)	0.0011 (6)	0.0049 (7)	0.0029 (7)
C9	0.0271 (8)	0.0246 (8)	0.0299 (10)	0.0011 (6)	0.0022 (7)	0.0017 (7)
C10	0.0313 (9)	0.0361 (9)	0.0482 (12)	−0.0030 (7)	−0.0046 (8)	0.0022 (9)
C11	0.0496 (11)	0.0346 (9)	0.0233 (10)	0.0021 (8)	−0.0032 (8)	−0.0025 (8)
C12	0.0341 (9)	0.0313 (9)	0.0344 (11)	−0.0002 (7)	−0.0015 (7)	−0.0027 (8)
C13	0.0357 (9)	0.0231 (8)	0.0270 (9)	−0.0011 (6)	0.0078 (7)	−0.0009 (7)
C14	0.0320 (8)	0.0206 (7)	0.0219 (9)	−0.0001 (6)	0.0052 (6)	−0.0004 (7)
C15	0.0358 (9)	0.0349 (9)	0.0249 (9)	−0.0010 (7)	0.0079 (7)	−0.0005 (8)
C16	0.0270 (8)	0.0268 (8)	0.0221 (9)	−0.0006 (6)	0.0064 (6)	−0.0003 (7)
C17	0.0268 (8)	0.0190 (7)	0.0207 (8)	−0.0017 (6)	0.0067 (6)	−0.0010 (6)
C18	0.0257 (8)	0.0194 (7)	0.0267 (9)	0.0016 (6)	0.0023 (7)	−0.0004 (7)
C19	0.0223 (7)	0.0240 (7)	0.0243 (9)	−0.0006 (5)	0.0059 (6)	0.0024 (7)
C20	0.0268 (8)	0.0328 (8)	0.0367 (10)	−0.0015 (6)	0.0021 (7)	0.0004 (8)

O1—C7	1.2202 (18)	C4—C5	1.385 (2)
O2—C17	1.2263 (16)	C4—C6	1.461 (2)
N1—C1	1.331 (2)	C5—H5	0.9500
N1—C5	1.3352 (19)	C6—H6	0.9500
N2—C6	1.2797 (19)	C8—C10	1.491 (2)
N2—N3	1.3719 (17)	C8—C9	1.492 (2)
N3—C7	1.3807 (18)	C9—H9A	0.9900
N3—C9	1.4534 (18)	C9—H9B	0.9900
N4—C7	1.3594 (19)	C10—H10A	0.9800
N4—N5	1.3832 (17)	C10—H10B	0.9800
N4—H4	0.8800	C10—H10C	0.9800
N5—C8	1.2701 (19)	C11—C12	1.383 (2)
N6—C11	1.332 (2)	C11—H11	0.9500
N6—C15	1.335 (2)	C12—C13	1.380 (2)
N7—C16	1.281 (2)	C12—H12	0.9500
N7—N8	1.3730 (17)	C13—C14	1.388 (2)
N8—C17	1.3795 (19)	C13—H13	0.9500
N8—C19	1.4536 (17)	C14—C15	1.394 (2)
N9—C17	1.3564 (19)	C14—C16	1.461 (2)
N9—N10	1.3867 (17)	C15—H15	0.9500
N9—H9	0.8800	C16—H16	0.9500
N10—C18	1.274 (2)	C18—C20	1.491 (2)
C1—C2	1.377 (2)	C18—C19	1.492 (2)
C1—H1	0.9500	C19—H19A	0.9900
C2—C3	1.379 (2)	C19—H19B	0.9900
C2—H2	0.9500	C20—H20A	0.9800
C3—C4	1.387 (2)	C20—H20B	0.9800
C3—H3	0.9500	C20—H20C	0.9800
C1—N1—C5	116.61 (13)	N3—C9—H9B	109.2
C6—N2—N3	117.97 (12)	C8—C9—H9B	109.2
N2—N3—C7	115.55 (12)	H9A—C9—H9B	107.9
N2—N3—C9	120.66 (11)	C8—C10—H10A	109.5
C7—N3—C9	123.66 (12)	C8—C10—H10B	109.5
C7—N4—N5	127.42 (12)	H10A—C10—H10B	109.5
C7—N4—H4	116.3	C8—C10—H10C	109.5
N5—N4—H4	116.3	H10A—C10—H10C	109.5
C8—N5—N4	117.31 (13)	H10B—C10—H10C	109.5
C11—N6—C15	117.07 (15)	N6—C11—C12	123.42 (16)
C16—N7—N8	117.67 (12)	N6—C11—H11	118.3
N7—N8—C17	115.60 (11)	C12—C11—H11	118.3
N7—N8—C19	121.02 (12)	C13—C12—C11	118.97 (16)
C17—N8—C19	123.36 (12)	C13—C12—H12	120.5
C17—N9—N10	127.41 (13)	C11—C12—H12	120.5
C17—N9—H9	116.3	C12—C13—C14	118.91 (16)
N10—N9—H9	116.3	C12—C13—H13	120.5
C18—N10—N9	116.63 (13)	C14—C13—H13	120.5
N1—C1—C2	123.36 (14)	C13—C14—C15	117.63 (15)
N1—C1—H1	118.3	C13—C14—C16	124.17 (15)
C2—C1—H1	118.3	C15—C14—C16	118.20 (14)
C1—C2—C3	119.24 (15)	N6—C15—C14	123.96 (15)
C1—C2—H2	120.4	N6—C15—H15	118.0
C3—C2—H2	120.4	C14—C15—H15	118.0
C2—C3—C4	118.79 (14)	N7—C16—C14	120.11 (14)
C2—C3—H3	120.6	N7—C16—H16	119.9
C4—C3—H3	120.6	C14—C16—H16	119.9
C5—C4—C3	117.30 (14)	O2—C17—N9	121.57 (14)
C5—C4—C6	119.41 (13)	O2—C17—N8	123.36 (14)
C3—C4—C6	123.28 (13)	N9—C17—N8	115.07 (12)
N1—C5—C4	124.65 (14)	N10—C18—C20	118.78 (14)
N1—C5—H5	117.7	N10—C18—C19	125.12 (13)
C4—C5—H5	117.7	C20—C18—C19	116.10 (14)
N2—C6—C4	119.22 (14)	N8—C19—C18	112.06 (12)
N2—C6—H6	120.4	N8—C19—H19A	109.2
C4—C6—H6	120.4	C18—C19—H19A	109.2
O1—C7—N4	121.57 (14)	N8—C19—H19B	109.2
O1—C7—N3	123.81 (14)	C18—C19—H19B	109.2
N4—C7—N3	114.60 (13)	H19A—C19—H19B	107.9
N5—C8—C10	119.06 (14)	C18—C20—H20A	109.5
N5—C8—C9	124.62 (14)	C18—C20—H20B	109.5
C10—C8—C9	116.31 (13)	H20A—C20—H20B	109.5
N3—C9—C8	112.26 (12)	C18—C20—H20C	109.5
N3—C9—H9A	109.2	H20A—C20—H20C	109.5
C8—C9—H9A	109.2	H20B—C20—H20C	109.5
C6—N2—N3—C7	177.92 (15)	C7—N3—C9—C8	1.3 (2)
C6—N2—N3—C9	−6.1 (2)	N5—C8—C9—N3	−1.1 (2)
C7—N4—N5—C8	4.1 (2)	C10—C8—C9—N3	178.12 (14)
C16—N7—N8—C17	172.24 (12)	C15—N6—C11—C12	0.4 (2)
C16—N7—N8—C19	−6.07 (19)	N6—C11—C12—C13	1.4 (3)
C17—N9—N10—C18	4.7 (2)	C11—C12—C13—C14	−1.7 (2)
C5—N1—C1—C2	−1.8 (3)	C12—C13—C14—C15	0.2 (2)
N1—C1—C2—C3	1.3 (3)	C12—C13—C14—C16	179.96 (14)
C1—C2—C3—C4	0.8 (3)	C11—N6—C15—C14	−2.0 (2)
C2—C3—C4—C5	−2.1 (2)	C13—C14—C15—N6	1.7 (2)
C2—C3—C4—C6	178.24 (16)	C16—C14—C15—N6	−178.07 (14)
C1—N1—C5—C4	0.3 (3)	N8—N7—C16—C14	179.00 (12)
C3—C4—C5—N1	1.7 (3)	C13—C14—C16—N7	−8.9 (2)
C6—C4—C5—N1	−178.69 (16)	C15—C14—C16—N7	170.84 (14)
N3—N2—C6—C4	179.19 (14)	N10—N9—C17—O2	174.79 (13)
C5—C4—C6—N2	174.00 (15)	N10—N9—C17—N8	−5.0 (2)
C3—C4—C6—N2	−6.4 (3)	N7—N8—C17—O2	1.8 (2)
N5—N4—C7—O1	177.59 (16)	C19—N8—C17—O2	−179.92 (13)
N5—N4—C7—N3	−3.9 (2)	N7—N8—C17—N9	−178.42 (11)
N2—N3—C7—O1	−4.7 (2)	C19—N8—C17—N9	−0.15 (19)
C9—N3—C7—O1	179.44 (15)	N9—N10—C18—C20	−178.69 (13)
N2—N3—C7—N4	176.77 (13)	N9—N10—C18—C19	0.8 (2)
C9—N3—C7—N4	1.0 (2)	N7—N8—C19—C18	−177.33 (11)
N4—N5—C8—C10	179.51 (15)	C17—N8—C19—C18	4.49 (19)
N4—N5—C8—C9	−1.3 (2)	N10—C18—C19—N8	−5.0 (2)
N2—N3—C9—C8	−174.34 (14)	C20—C18—C19—N8	174.58 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2i	0.88	2.32	2.9545 (17)	129
N4—H4···N7i	0.88	2.43	3.2346 (17)	152
N9—H9···N6ii	0.88	2.04	2.882 (2)	159
C19—H19A···N1iii	0.99	2.57	3.0852 (19)	112
C19—H19A···O1iv	0.99	2.60	3.5596 (19)	164
C20—H20C···O1v	0.98	2.53	3.3906 (19)	147

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N4H4O2i	0.88	2.32	2.9545(17)	129
N4H4N7i	0.88	2.43	3.2346(17)	152
N9H9N6ii	0.88	2.04	2.882(2)	159
C19H19AN1iii	0.99	2.57	3.0852(19)	112
C19H19AO1iv	0.99	2.60	3.5596(19)	164
C20H20CO1v	0.98	2.53	3.3906(19)	147

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