(E)-2-{1-[(6-Chloro-pyridin-3-yl)meth-yl]imidazolidin-2-yl-idene}-2-cyano-N-(2-methylphenyl)acetamide.

In the title compound, C(19)H(18)N(5)O, the imidazolidine ring makes dihedral angles of 87.62 (17) and 28.27 (11)° with the pyridine and benzene rings, respectively. An intra-molecular N-H⋯O hydrogen bond is observed between the carbonyl O atom and an imidazolidine H atom. In the crystal, an inter-molecular N-H⋯N hydrogen bond gives rise to a linear chain running along the b axis.

Related literature

For background to neonicotinoids and their biological activity, see: Shao et al. (2008 ▶); Nishimura et al. (1994 ▶); Mori et al. (2002 ▶); Ohno et al. (2009 ▶); Tomizawa et al. (2000 ▶); Wu et al. (2011 ▶).

Experimental

Crystal data

C19H18ClN5O

M = 367.83

Monoclinic,

a = 16.2019 (18) Å

b = 7.6240 (9) Å

c = 14.7368 (18) Å

β = 97.007 (3)°

V = 1806.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.26 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997) ▶ T min = 0.943, T max = 0.953

19209 measured reflections

3512 independent reflections

2618 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.139

S = 1.03

3512 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037524/ng5220sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037524/ng5220Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037524/ng5220Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811037524/ng5220Isup4.cml

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

C19H18ClN5O	F(000) = 768
Mr = 367.83	Dx = 1.352 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19209 reflections
a = 16.2019 (18) Å	θ = 1.3–26.0°
b = 7.6240 (9) Å	µ = 0.23 mm−1
c = 14.7368 (18) Å	T = 293 K
β = 97.007 (3)°	Prism, colourless
V = 1806.7 (4) Å3	0.26 × 0.23 × 0.21 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3512 independent reflections
Radiation source: fine-focus sealed tube	2618 reflections with I > 2σ(I)
graphite	Rint = 0.060
φ and ω scans	θmax = 26.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −19→19
Tmin = 0.943, Tmax = 0.953	k = −9→9
19209 measured reflections	l = −18→17

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0717P)2 + 0.3718P] where P = (Fo2 + 2Fc2)/3
3512 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.28 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
C1	0.48863 (12)	−0.2075 (2)	−0.41527 (13)	0.0530 (5)
C2	0.42330 (13)	−0.1992 (3)	−0.48356 (13)	0.0598 (5)
H2	0.4244	−0.2600	−0.5381	0.072*
C3	0.35610 (13)	−0.0979 (3)	−0.46850 (13)	0.0552 (5)
H3	0.3105	−0.0890	−0.5132	0.066*
C4	0.35663 (11)	−0.0093 (2)	−0.38658 (12)	0.0477 (4)
C5	0.42631 (13)	−0.0274 (3)	−0.32411 (14)	0.0623 (6)
H5	0.4278	0.0335	−0.2693	0.075*
C6	0.28226 (13)	0.0973 (3)	−0.36788 (15)	0.0641 (6)
H6A	0.2542	0.1407	−0.4254	0.077*
H6B	0.2437	0.0219	−0.3407	0.077*
N2	0.30409 (10)	0.2454 (2)	−0.30700 (11)	0.0570 (4)
C8	0.32548 (15)	0.5482 (3)	−0.28080 (15)	0.0673 (6)
H8A	0.3771	0.5860	−0.2461	0.081*
H8B	0.2989	0.6479	−0.3132	0.081*
C9	0.26236 (11)	0.2939 (2)	−0.23634 (12)	0.0497 (5)
C10	0.22032 (12)	0.1820 (2)	−0.18154 (13)	0.0506 (5)
C11	0.23108 (16)	−0.0018 (3)	−0.18395 (18)	0.0735 (6)
C12	0.17737 (11)	0.2533 (2)	−0.10901 (12)	0.0479 (4)
H12B	0.1949	−0.1608	0.0393	0.108 (10)*
H12C	0.1391	−0.2427	0.1011	0.117 (11)*
H12A	0.1041	−0.2307	−0.0043	0.133 (11)*
C13	0.10396 (11)	0.1528 (3)	0.02201 (14)	0.0540 (5)
C14	0.07069 (13)	0.3118 (3)	0.04596 (15)	0.0631 (6)
H14	0.0718	0.4087	0.0078	0.076*
C15	0.03602 (16)	0.3252 (4)	0.12656 (17)	0.0790 (7)
H15	0.0133	0.4313	0.1424	0.095*
C16	0.03473 (18)	0.1828 (4)	0.18372 (18)	0.0889 (8)
H16	0.0118	0.1928	0.2384	0.107*
C17	0.06735 (16)	0.0262 (4)	0.15965 (18)	0.0836 (7)
H17	0.0658	−0.0694	0.1986	0.100*
C18	0.10247 (13)	0.0055 (3)	0.07951 (16)	0.0652 (6)
C19	0.13699 (18)	−0.1683 (3)	0.0544 (2)	0.0883 (8)
N1	0.49193 (11)	−0.1261 (2)	−0.33656 (12)	0.0644 (5)
C7	0.33994 (16)	0.4000 (3)	−0.34602 (16)	0.0731 (7)
H7A	0.3124	0.4240	−0.4069	0.088*
H7B	0.3989	0.3835	−0.3493	0.088*
N3	0.27094 (11)	0.4658 (2)	−0.22247 (11)	0.0592 (4)
H3A	0.2465	0.5223	−0.1828	0.071*
N4	0.2387 (2)	−0.1517 (3)	−0.1790 (2)	0.1184 (10)
N5	0.13992 (11)	0.1309 (2)	−0.05957 (12)	0.0611 (5)
H5A	0.1381	0.0262	−0.0814	0.073*
O1	0.17555 (9)	0.41125 (17)	−0.09060 (9)	0.0620 (4)
Cl1	0.57548 (4)	−0.33450 (9)	−0.43072 (4)	0.0805 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0587 (11)	0.0458 (10)	0.0560 (11)	0.0075 (8)	0.0131 (9)	−0.0006 (9)
C2	0.0789 (13)	0.0558 (12)	0.0450 (11)	0.0146 (10)	0.0080 (9)	−0.0111 (9)
C3	0.0672 (12)	0.0540 (11)	0.0427 (10)	0.0125 (9)	−0.0005 (8)	−0.0057 (8)
C4	0.0561 (10)	0.0442 (10)	0.0431 (10)	0.0042 (8)	0.0076 (8)	−0.0042 (8)
C5	0.0650 (12)	0.0714 (14)	0.0496 (11)	0.0127 (10)	0.0032 (9)	−0.0184 (10)
C6	0.0623 (12)	0.0744 (14)	0.0548 (12)	0.0141 (10)	0.0040 (9)	−0.0206 (10)
N2	0.0692 (10)	0.0508 (10)	0.0532 (9)	0.0108 (8)	0.0160 (8)	−0.0081 (8)
C8	0.0861 (15)	0.0555 (12)	0.0639 (13)	0.0111 (11)	0.0236 (11)	0.0056 (10)
C9	0.0564 (10)	0.0471 (11)	0.0452 (10)	0.0146 (8)	0.0046 (8)	−0.0048 (8)
C10	0.0572 (11)	0.0408 (10)	0.0540 (11)	0.0068 (8)	0.0072 (8)	−0.0082 (8)
C11	0.0889 (16)	0.0509 (14)	0.0875 (16)	0.0048 (11)	0.0375 (13)	−0.0124 (11)
C12	0.0520 (10)	0.0436 (10)	0.0473 (10)	0.0052 (8)	0.0027 (8)	−0.0048 (8)
C13	0.0453 (10)	0.0568 (12)	0.0600 (12)	−0.0044 (8)	0.0067 (8)	−0.0024 (9)
C14	0.0614 (12)	0.0642 (14)	0.0654 (13)	0.0096 (10)	0.0145 (10)	0.0006 (10)
C15	0.0834 (16)	0.0865 (18)	0.0714 (15)	0.0118 (13)	0.0267 (13)	−0.0074 (13)
C16	0.0936 (19)	0.108 (2)	0.0700 (16)	0.0016 (16)	0.0287 (14)	0.0055 (16)
C17	0.0858 (17)	0.0905 (19)	0.0765 (17)	−0.0106 (14)	0.0182 (14)	0.0223 (14)
C18	0.0568 (11)	0.0588 (13)	0.0791 (15)	−0.0077 (10)	0.0051 (11)	0.0058 (11)
C19	0.0933 (19)	0.0552 (15)	0.117 (2)	−0.0042 (13)	0.0150 (16)	0.0151 (15)
N1	0.0613 (10)	0.0739 (12)	0.0561 (10)	0.0134 (9)	−0.0004 (8)	−0.0134 (9)
C7	0.0949 (17)	0.0642 (14)	0.0654 (14)	0.0189 (12)	0.0303 (12)	0.0051 (11)
N3	0.0820 (11)	0.0422 (9)	0.0569 (10)	0.0107 (8)	0.0229 (8)	−0.0018 (7)
N4	0.178 (3)	0.0454 (13)	0.150 (2)	0.0096 (14)	0.092 (2)	−0.0105 (13)
N5	0.0693 (11)	0.0447 (9)	0.0724 (12)	−0.0027 (8)	0.0210 (9)	−0.0106 (8)
O1	0.0873 (10)	0.0426 (8)	0.0596 (9)	0.0034 (7)	0.0229 (7)	−0.0087 (6)
Cl1	0.0730 (4)	0.0846 (5)	0.0850 (5)	0.0292 (3)	0.0141 (3)	−0.0110 (3)

C1—N1	1.311 (3)	C10—C12	1.450 (3)
C1—C2	1.370 (3)	C11—N4	1.151 (3)
C1—Cl1	1.7458 (19)	C12—O1	1.236 (2)
C2—C3	1.375 (3)	C12—N5	1.370 (3)
C2—H2	0.9300	C13—C14	1.390 (3)
C3—C4	1.383 (3)	C13—N5	1.408 (3)
C3—H3	0.9300	C13—C18	1.408 (3)
C4—C5	1.374 (3)	C14—C15	1.378 (3)
C4—C6	1.506 (3)	C14—H14	0.9300
C5—N1	1.334 (3)	C15—C16	1.376 (4)
C5—H5	0.9300	C15—H15	0.9300
C6—N2	1.459 (3)	C16—C17	1.370 (4)
C6—H6A	0.9700	C16—H16	0.9300
C6—H6B	0.9700	C17—C18	1.381 (4)
N2—C9	1.360 (2)	C17—H17	0.9300
N2—C7	1.462 (3)	C18—C19	1.502 (4)
C8—N3	1.449 (3)	C19—H12B	0.9917
C8—C7	1.520 (3)	C19—H12C	0.8887
C8—H8A	0.9700	C19—H12A	1.0711
C8—H8B	0.9700	C7—H7A	0.9700
C9—N3	1.331 (2)	C7—H7B	0.9700
C9—C10	1.407 (3)	N3—H3A	0.8600
C10—C11	1.413 (3)	N5—H5A	0.8600
N1—C1—C2	124.94 (18)	N5—C12—C10	114.85 (16)
N1—C1—Cl1	115.56 (15)	C14—C13—N5	122.25 (19)
C2—C1—Cl1	119.50 (15)	C14—C13—C18	120.5 (2)
C1—C2—C3	117.60 (18)	N5—C13—C18	117.29 (19)
C1—C2—H2	121.2	C15—C14—C13	119.7 (2)
C3—C2—H2	121.2	C15—C14—H14	120.2
C2—C3—C4	119.67 (18)	C13—C14—H14	120.2
C2—C3—H3	120.2	C16—C15—C14	120.5 (2)
C4—C3—H3	120.2	C16—C15—H15	119.8
C5—C4—C3	116.93 (17)	C14—C15—H15	119.8
C5—C4—C6	122.82 (17)	C17—C16—C15	119.6 (2)
C3—C4—C6	120.23 (17)	C17—C16—H16	120.2
N1—C5—C4	124.64 (18)	C15—C16—H16	120.2
N1—C5—H5	117.7	C16—C17—C18	122.2 (2)
C4—C5—H5	117.7	C16—C17—H17	118.9
N2—C6—C4	113.00 (17)	C18—C17—H17	118.9
N2—C6—H6A	109.0	C17—C18—C13	117.6 (2)
C4—C6—H6A	109.0	C17—C18—C19	121.1 (2)
N2—C6—H6B	109.0	C13—C18—C19	121.4 (2)
C4—C6—H6B	109.0	C18—C19—H12B	113.3
H6A—C6—H6B	107.8	C18—C19—H12C	110.6
C9—N2—C6	125.12 (18)	H12B—C19—H12C	105.3
C9—N2—C7	109.92 (16)	C18—C19—H12A	115.3
C6—N2—C7	117.40 (17)	H12B—C19—H12A	103.6
N3—C8—C7	101.83 (18)	H12C—C19—H12A	108.1
N3—C8—H8A	111.4	C1—N1—C5	116.21 (17)
C7—C8—H8A	111.4	N2—C7—C8	104.54 (17)
N3—C8—H8B	111.4	N2—C7—H7A	110.8
C7—C8—H8B	111.4	C8—C7—H7A	110.8
H8A—C8—H8B	109.3	N2—C7—H7B	110.8
N3—C9—N2	109.43 (17)	C8—C7—H7B	110.8
N3—C9—C10	123.91 (16)	H7A—C7—H7B	108.9
N2—C9—C10	126.56 (17)	C9—N3—C8	113.30 (16)
C9—C10—C11	121.14 (18)	C9—N3—H3A	123.3
C9—C10—C12	120.36 (16)	C8—N3—H3A	123.3
C11—C10—C12	117.51 (19)	C12—N5—C13	129.02 (17)
N4—C11—C10	174.7 (3)	C12—N5—H5A	115.5
O1—C12—N5	121.52 (17)	C13—N5—H5A	115.5
O1—C12—C10	123.60 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N4i	0.86	2.49	3.044 (3)	123.
N3—H3A···O1	0.86	2.07	2.659 (2)	126.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N4i	0.86	2.49	3.044 (3)	123
N3—H3A⋯O1	0.86	2.07	2.659 (2)	126

Symmetry code: (i) .