2-(Meth-oxy-imino)-2-{2-[(2-methyl-phenoxy)meth-yl]phen-yl}acetohydrazide.

In the title mol-ecule, C(17)H(19)N(3)O(3), the dihedral angle between the two benzene rings is 57.17 (5)°. In the crystal, N-H⋯O and N-H⋯N hydrogen bonds connect mol-ecules to form chains along [001]. In addition, a weak C-H⋯π inter-action is observed.

Related literature

For the biological activities of kresoxim-methyl {methyl 2(E)-meth­oxy­imino-2-[2-(2-tolyl­oxymeth­yl)phen­yl] acetate}, which is a starting material in the synthesis of the title compound, see: Anke et al. (1977 ▶); Balba (2007 ▶); Ichinari et al. (1999 ▶); Grossmann & Retzlaff (1997 ▶); Ypema (1998 ▶). For the crystal structure of kresoxim-methyl, see: Chopra et al. (2004 ▶).

Experimental

Crystal data

C17H19N3O3

M = 313.35

Monoclinic,

a = 21.4015 (6) Å

b = 20.7277 (4) Å

c = 7.6975 (2) Å

β = 109.103 (3)°

V = 3226.60 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.906, T max = 1.000

55120 measured reflections

3174 independent reflections

2532 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.02

3174 reflections

222 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681203070X/lh5499sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203070X/lh5499Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203070X/lh5499Isup3.cml

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

C17H19N3O3	F(000) = 1328
Mr = 313.35	Dx = 1.290 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 21236 reflections
a = 21.4015 (6) Å	θ = 3.5–29.1°
b = 20.7277 (4) Å	µ = 0.09 mm−1
c = 7.6975 (2) Å	T = 293 K
β = 109.103 (3)°	Block, white
V = 3226.60 (14) Å3	0.3 × 0.2 × 0.2 mm
Z = 8

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3174 independent reflections
Radiation source: fine-focus sealed tube	2532 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scan	h = −26→26
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −25→25
Tmin = 0.906, Tmax = 1.000	l = −9→9
55120 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0448P)2 + 1.9045P] where P = (Fo2 + 2Fc2)/3
3174 reflections	(Δ/σ)max = 0.001
222 parameters	Δρmax = 0.18 e Å−3
3 restraints	Δρmin = −0.17 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
N3	0.10242 (6)	0.35418 (5)	0.94034 (15)	0.0383 (3)
N6	0.08078 (6)	0.46145 (6)	0.74149 (16)	0.0391 (3)
N7	0.06911 (8)	0.51996 (6)	0.64119 (18)	0.0453 (3)
O15	0.23561 (6)	0.35236 (5)	0.70574 (15)	0.0510 (3)
O4	0.11743 (6)	0.29666 (5)	1.03992 (13)	0.0466 (3)
O1	0.06825 (6)	0.40146 (5)	0.48718 (13)	0.0521 (3)
C17	0.28955 (8)	0.44911 (8)	0.6901 (2)	0.0519 (4)
C18	0.34451 (11)	0.48795 (10)	0.7505 (3)	0.0694 (6)
H18	0.3437	0.5282	0.6965	0.083*
C19	0.40054 (11)	0.46909 (12)	0.8882 (3)	0.0808 (7)
H19	0.4372	0.4961	0.9252	0.097*
C20	0.40213 (10)	0.41013 (11)	0.9710 (3)	0.0706 (6)
H20	0.4400	0.3972	1.0645	0.085*
C21	0.34756 (8)	0.36974 (9)	0.9158 (2)	0.0546 (4)
H21	0.3484	0.3300	0.9728	0.066*
C16	0.29186 (8)	0.38918 (8)	0.7750 (2)	0.0444 (4)
C22	0.22894 (10)	0.47007 (10)	0.5382 (3)	0.0728 (6)
H22A	0.2339	0.5142	0.5069	0.109*
H22B	0.1910	0.4662	0.5780	0.109*
H22C	0.2231	0.4432	0.4324	0.109*
C14	0.23124 (8)	0.29575 (7)	0.8055 (2)	0.0453 (4)
H14A	0.2306	0.3074	0.9270	0.054*
H14B	0.2695	0.2685	0.8198	0.054*
C13	0.16963 (7)	0.26008 (7)	0.70408 (19)	0.0382 (3)
C12	0.17407 (9)	0.20035 (8)	0.6249 (2)	0.0523 (4)
H12	0.2155	0.1838	0.6353	0.063*
C11	0.11869 (11)	0.16554 (8)	0.5321 (3)	0.0603 (5)
H11	0.1228	0.1257	0.4814	0.072*
C10	0.05738 (10)	0.18966 (9)	0.5143 (2)	0.0593 (5)
H10	0.0198	0.1663	0.4507	0.071*
C9	0.05121 (8)	0.24886 (8)	0.5911 (2)	0.0473 (4)
H9	0.0094	0.2650	0.5783	0.057*
C8	0.10689 (7)	0.28413 (6)	0.68670 (18)	0.0347 (3)
C2	0.09848 (7)	0.34665 (6)	0.77269 (18)	0.0320 (3)
C5	0.11414 (11)	0.30815 (9)	1.2204 (2)	0.0608 (5)
H5A	0.1481	0.3382	1.2840	0.091*
H5B	0.1205	0.2683	1.2873	0.091*
H5C	0.0716	0.3257	1.2106	0.091*
C1	0.08095 (7)	0.40622 (7)	0.65305 (18)	0.0334 (3)
H61	0.0840 (8)	0.4629 (7)	0.8568 (13)	0.041 (4)*
H71	0.0964 (9)	0.5477 (8)	0.707 (3)	0.081 (7)*
H72	0.0295 (6)	0.5333 (11)	0.627 (3)	0.090 (8)*

	U11	U22	U33	U12	U13	U23
N3	0.0523 (7)	0.0327 (6)	0.0321 (6)	0.0099 (5)	0.0169 (5)	0.0061 (5)
N6	0.0587 (8)	0.0320 (6)	0.0273 (6)	0.0039 (5)	0.0149 (6)	0.0027 (5)
N7	0.0656 (10)	0.0306 (7)	0.0381 (7)	0.0039 (7)	0.0147 (7)	0.0031 (5)
O15	0.0515 (7)	0.0461 (6)	0.0510 (7)	−0.0027 (5)	0.0109 (5)	0.0143 (5)
O4	0.0752 (8)	0.0367 (6)	0.0327 (5)	0.0146 (5)	0.0244 (5)	0.0094 (4)
O1	0.0866 (9)	0.0427 (6)	0.0291 (5)	0.0151 (6)	0.0215 (5)	0.0035 (4)
C17	0.0549 (10)	0.0522 (10)	0.0582 (10)	−0.0013 (8)	0.0317 (8)	0.0044 (8)
C18	0.0698 (14)	0.0621 (12)	0.0891 (15)	−0.0130 (10)	0.0435 (12)	−0.0013 (11)
C19	0.0598 (13)	0.0881 (16)	0.1030 (18)	−0.0239 (12)	0.0382 (13)	−0.0213 (14)
C20	0.0448 (11)	0.0892 (16)	0.0760 (13)	0.0057 (10)	0.0172 (9)	−0.0183 (12)
C21	0.0504 (10)	0.0566 (10)	0.0577 (10)	0.0075 (8)	0.0188 (8)	−0.0050 (8)
C16	0.0443 (9)	0.0451 (9)	0.0491 (9)	0.0019 (7)	0.0226 (7)	−0.0006 (7)
C22	0.0763 (14)	0.0638 (12)	0.0795 (14)	−0.0005 (10)	0.0271 (11)	0.0313 (10)
C14	0.0445 (9)	0.0439 (9)	0.0489 (9)	0.0101 (7)	0.0171 (7)	0.0141 (7)
C13	0.0481 (9)	0.0341 (7)	0.0373 (7)	0.0075 (6)	0.0209 (6)	0.0088 (6)
C12	0.0712 (12)	0.0402 (9)	0.0566 (10)	0.0157 (8)	0.0360 (9)	0.0073 (7)
C11	0.0990 (16)	0.0358 (9)	0.0598 (11)	−0.0025 (9)	0.0446 (11)	−0.0069 (8)
C10	0.0804 (13)	0.0514 (10)	0.0523 (10)	−0.0246 (9)	0.0303 (9)	−0.0129 (8)
C9	0.0503 (9)	0.0516 (9)	0.0451 (9)	−0.0055 (7)	0.0225 (7)	−0.0034 (7)
C8	0.0457 (8)	0.0328 (7)	0.0299 (7)	0.0028 (6)	0.0184 (6)	0.0041 (5)
C2	0.0339 (7)	0.0331 (7)	0.0307 (7)	0.0043 (5)	0.0130 (6)	0.0027 (5)
C5	0.0999 (15)	0.0554 (10)	0.0335 (8)	0.0123 (10)	0.0307 (9)	0.0089 (7)
C1	0.0367 (7)	0.0359 (7)	0.0297 (7)	0.0058 (6)	0.0136 (6)	0.0028 (5)

N3—C2	1.2750 (17)	C22—H22A	0.9600
N3—O4	1.3968 (14)	C22—H22B	0.9600
N6—C1	1.3326 (17)	C22—H22C	0.9600
N6—N7	1.4153 (17)	C14—C13	1.490 (2)
N6—H61	0.868 (9)	C14—H14A	0.9700
N7—H71	0.858 (10)	C14—H14B	0.9700
N7—H72	0.864 (10)	C13—C12	1.397 (2)
O15—C16	1.3767 (19)	C13—C8	1.397 (2)
O15—C14	1.4222 (17)	C12—C11	1.372 (3)
O4—C5	1.4335 (18)	C12—H12	0.9300
O1—C1	1.2192 (16)	C11—C10	1.369 (3)
C17—C18	1.375 (3)	C11—H11	0.9300
C17—C16	1.397 (2)	C10—C9	1.387 (2)
C17—C22	1.498 (3)	C10—H10	0.9300
C18—C19	1.372 (3)	C9—C8	1.387 (2)
C18—H18	0.9300	C9—H9	0.9300
C19—C20	1.374 (3)	C8—C2	1.4926 (18)
C19—H19	0.9300	C2—C1	1.5123 (18)
C20—C21	1.386 (3)	C5—H5A	0.9600
C20—H20	0.9300	C5—H5B	0.9600
C21—C16	1.383 (2)	C5—H5C	0.9600
C21—H21	0.9300
C2—N3—O4	112.21 (11)	C13—C14—H14A	109.8
C1—N6—N7	119.14 (11)	O15—C14—H14B	109.8
C1—N6—H61	122.7 (10)	C13—C14—H14B	109.8
N7—N6—H61	117.9 (10)	H14A—C14—H14B	108.3
N6—N7—H71	106.7 (15)	C12—C13—C8	118.36 (15)
N6—N7—H72	109.5 (16)	C12—C13—C14	119.56 (14)
H71—N7—H72	108 (2)	C8—C13—C14	122.07 (13)
C16—O15—C14	116.85 (12)	C11—C12—C13	121.52 (16)
N3—O4—C5	108.33 (11)	C11—C12—H12	119.2
C18—C17—C16	117.83 (17)	C13—C12—H12	119.2
C18—C17—C22	121.37 (17)	C10—C11—C12	119.78 (15)
C16—C17—C22	120.80 (16)	C10—C11—H11	120.1
C19—C18—C17	122.0 (2)	C12—C11—H11	120.1
C19—C18—H18	119.0	C11—C10—C9	120.17 (17)
C17—C18—H18	119.0	C11—C10—H10	119.9
C18—C19—C20	119.6 (2)	C9—C10—H10	119.9
C18—C19—H19	120.2	C10—C9—C8	120.50 (16)
C20—C19—H19	120.2	C10—C9—H9	119.7
C19—C20—C21	120.3 (2)	C8—C9—H9	119.7
C19—C20—H20	119.8	C9—C8—C13	119.66 (13)
C21—C20—H20	119.8	C9—C8—C2	119.06 (13)
C16—C21—C20	119.22 (18)	C13—C8—C2	121.27 (13)
C16—C21—H21	120.4	N3—C2—C8	125.28 (12)
C20—C21—H21	120.4	N3—C2—C1	115.94 (11)
O15—C16—C21	124.22 (15)	C8—C2—C1	118.73 (11)
O15—C16—C17	114.76 (14)	O4—C5—H5A	109.5
C21—C16—C17	121.01 (16)	O4—C5—H5B	109.5
C17—C22—H22A	109.5	H5A—C5—H5B	109.5
C17—C22—H22B	109.5	O4—C5—H5C	109.5
H22A—C22—H22B	109.5	H5A—C5—H5C	109.5
C17—C22—H22C	109.5	H5B—C5—H5C	109.5
H22A—C22—H22C	109.5	O1—C1—N6	124.57 (13)
H22B—C22—H22C	109.5	O1—C1—C2	119.84 (12)
O15—C14—C13	109.25 (12)	N6—C1—C2	115.59 (11)
O15—C14—H14A	109.8
C2—N3—O4—C5	−174.13 (14)	C12—C11—C10—C9	−0.5 (3)
C16—C17—C18—C19	0.7 (3)	C11—C10—C9—C8	−0.1 (2)
C22—C17—C18—C19	−179.34 (19)	C10—C9—C8—C13	0.7 (2)
C17—C18—C19—C20	−0.9 (3)	C10—C9—C8—C2	−178.03 (13)
C18—C19—C20—C21	0.1 (3)	C12—C13—C8—C9	−0.6 (2)
C19—C20—C21—C16	0.8 (3)	C14—C13—C8—C9	−179.88 (13)
C14—O15—C16—C21	10.5 (2)	C12—C13—C8—C2	178.12 (12)
C14—O15—C16—C17	−170.36 (13)	C14—C13—C8—C2	−1.2 (2)
C20—C21—C16—O15	178.15 (15)	O4—N3—C2—C8	1.5 (2)
C20—C21—C16—C17	−1.0 (2)	O4—N3—C2—C1	178.76 (11)
C18—C17—C16—O15	−178.97 (15)	C9—C8—C2—N3	96.60 (18)
C22—C17—C16—O15	1.1 (2)	C13—C8—C2—N3	−82.08 (18)
C18—C17—C16—C21	0.2 (2)	C9—C8—C2—C1	−80.61 (16)
C22—C17—C16—C21	−179.71 (17)	C13—C8—C2—C1	100.71 (15)
C16—O15—C14—C13	−176.27 (12)	N7—N6—C1—O1	−4.0 (2)
O15—C14—C13—C12	111.95 (15)	N7—N6—C1—C2	175.93 (13)
O15—C14—C13—C8	−68.73 (17)	N3—C2—C1—O1	−170.98 (14)
C8—C13—C12—C11	−0.1 (2)	C8—C2—C1—O1	6.5 (2)
C14—C13—C12—C11	179.25 (14)	N3—C2—C1—N6	9.09 (19)
C13—C12—C11—C10	0.6 (3)	C8—C2—C1—N6	−173.44 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H72···O1i	0.86 (2)	2.40 (2)	3.220 (2)	158 (2)
N6—H61···N7ii	0.87 (2)	2.34 (1)	3.191 (2)	166 (1)
C5—H5B···Cgiii	0.96	2.69	3.461 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg refers to the centroid of the C8–C13 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H72⋯O1i	0.86 (2)	2.40 (2)	3.220 (2)	158 (2)
N6—H61⋯N7ii	0.87 (2)	2.34 (1)	3.191 (2)	166 (1)
C5—H5B⋯Cg iii	0.96	2.69	3.461 (2)	138

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