Methyl (E)-2-({2-[(E)-(hy-droxy-imino)-meth-yl]phen-oxy}meth-yl)-3-(4-methyl-phen-yl)acrylate.

In the title compound, C(19)H(19)NO(4), the dihedral angle between the mean planes through the benzene rings is 82.18 (7)°. The C=N double bond is trans-configured. The mol-ecules are linked into centrosymmetric dimers via pairs of O-H⋯N hydrogen bonds with the motif R(2) (2)(6). The crystal packing also features C-H⋯O inter-actions. The methyl group attached to one of the aromatic rings is disordered over two almost equally occupied positions [occpancy ratio = 0.51 (4):0.49 (4)].

Related literature

For information on oximes, see: Chaudhuri (2003 ▶). For a related structure, see: SakthiMurugesan et al. (2011 ▶).

Experimental

Crystal data

C19H19NO4

M = 325.35

Triclinic,

a = 8.8683 (2) Å

b = 9.3246 (2) Å

c = 11.9259 (3) Å

α = 75.200 (2)°

β = 76.453 (2)°

γ = 65.142 (1)°

V = 856.04 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 0.978

20292 measured reflections

4580 independent reflections

3493 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.132

S = 1.04

4580 reflections

221 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019046/bt5884sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019046/bt5884Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019046/bt5884Isup3.cml

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

C19H19NO4	Z = 2
Mr = 325.35	F(000) = 344
Triclinic, P1	Dx = 1.262 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8683 (2) Å	Cell parameters from 6056 reflections
b = 9.3246 (2) Å	θ = 2.5–32.5°
c = 11.9259 (3) Å	µ = 0.09 mm−1
α = 75.200 (2)°	T = 293 K
β = 76.453 (2)°	Block, white crystalline
γ = 65.142 (1)°	0.35 × 0.30 × 0.25 mm
V = 856.04 (3) Å3

Bruker APEXII CCD area-detector diffractometer	4580 independent reflections
Radiation source: fine-focus sealed tube	3493 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω and φ scans	θmax = 29.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.970, Tmax = 0.978	k = −12→12
20292 measured reflections	l = −16→16

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.1563P] where P = (Fo2 + 2Fc2)/3
4580 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 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	Occ. (<1)
C1	0.30137 (15)	0.78709 (15)	0.40342 (11)	0.0446 (3)
H1	0.3839	0.8244	0.3607	0.053*
C2	0.32860 (14)	0.61892 (14)	0.41323 (10)	0.0397 (3)
C3	0.24555 (17)	0.54149 (16)	0.50493 (12)	0.0521 (3)
H3	0.1701	0.5977	0.5623	0.063*
C4	0.2729 (2)	0.38274 (18)	0.51246 (13)	0.0608 (4)
H4	0.2161	0.3325	0.5743	0.073*
C5	0.38495 (19)	0.29887 (16)	0.42785 (13)	0.0569 (3)
H5	0.4027	0.1920	0.4326	0.068*
C6	0.47131 (16)	0.37155 (15)	0.33607 (12)	0.0476 (3)
H6	0.5470	0.3139	0.2795	0.057*
C7	0.44431 (14)	0.53102 (13)	0.32886 (10)	0.0385 (2)
C8	0.64247 (16)	0.53394 (14)	0.15207 (11)	0.0450 (3)
H8A	0.5849	0.5135	0.1017	0.054*
H8B	0.7225	0.4320	0.1859	0.054*
C9	0.73103 (15)	0.64103 (15)	0.08311 (11)	0.0441 (3)
C10	0.89857 (17)	0.60977 (17)	0.11066 (13)	0.0532 (3)
C11	1.0978 (2)	0.4600 (3)	0.24022 (17)	0.0852 (6)
H11A	1.1801	0.4565	0.1713	0.128*
H11B	1.1307	0.3571	0.2908	0.128*
H11C	1.0899	0.5402	0.2807	0.128*
C12	0.67354 (16)	0.76491 (15)	−0.00294 (11)	0.0475 (3)
H12	0.7450	0.8193	−0.0359	0.057*
C13	0.51907 (16)	0.82972 (14)	−0.05413 (11)	0.0456 (3)
C14	0.37187 (17)	0.80613 (17)	−0.00162 (12)	0.0546 (3)
H14	0.3663	0.7467	0.0737	0.065*
C15	0.23412 (19)	0.86949 (18)	−0.05950 (14)	0.0594 (4)
H15	0.1378	0.8506	−0.0228	0.071*
C16	0.23571 (19)	0.96063 (17)	−0.17098 (13)	0.0578 (4)
C17	0.3798 (2)	0.98842 (18)	−0.22200 (13)	0.0619 (4)
H17	0.3833	1.0512	−0.2962	0.074*
C18	0.51779 (19)	0.92530 (16)	−0.16541 (12)	0.0558 (3)
H18	0.6129	0.9466	−0.2020	0.067*
C19	0.0852 (3)	1.0257 (3)	−0.23393 (18)	0.0884 (6)
H19A	0.0030	0.9840	−0.1886	0.133*	0.51 (4)
H19B	0.1192	0.9937	−0.3093	0.133*	0.51 (4)
H19C	0.0376	1.1408	−0.2440	0.133*	0.51 (4)
H19D	0.0618	0.9382	−0.2433	0.133*	0.49 (4)
H19F	0.1082	1.0858	−0.3096	0.133*	0.49 (4)
H19E	−0.0102	1.0945	−0.1890	0.133*	0.49 (4)
N1	0.16707 (14)	0.88269 (13)	0.45217 (10)	0.0493 (3)
O1	0.16721 (14)	1.03758 (12)	0.43411 (11)	0.0699 (3)
H1A	0.0766	1.0977	0.4635	0.105*
O2	0.52349 (11)	0.61418 (10)	0.24323 (7)	0.0467 (2)
O3	0.99150 (15)	0.67203 (16)	0.05342 (13)	0.0872 (4)
O4	0.93678 (13)	0.49931 (16)	0.20693 (9)	0.0720 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0417 (6)	0.0459 (6)	0.0413 (6)	−0.0165 (5)	0.0028 (5)	−0.0081 (5)
C2	0.0363 (5)	0.0416 (6)	0.0369 (5)	−0.0131 (4)	−0.0052 (4)	−0.0034 (4)
C3	0.0498 (7)	0.0526 (7)	0.0433 (6)	−0.0177 (6)	0.0034 (5)	−0.0034 (5)
C4	0.0628 (9)	0.0551 (8)	0.0556 (8)	−0.0281 (7)	0.0009 (7)	0.0061 (6)
C5	0.0620 (8)	0.0428 (6)	0.0639 (8)	−0.0235 (6)	−0.0082 (7)	−0.0009 (6)
C6	0.0480 (7)	0.0427 (6)	0.0502 (7)	−0.0160 (5)	−0.0055 (5)	−0.0095 (5)
C7	0.0366 (5)	0.0407 (6)	0.0362 (5)	−0.0144 (4)	−0.0063 (4)	−0.0032 (4)
C8	0.0453 (6)	0.0428 (6)	0.0431 (6)	−0.0146 (5)	0.0033 (5)	−0.0141 (5)
C9	0.0415 (6)	0.0467 (6)	0.0424 (6)	−0.0162 (5)	0.0055 (5)	−0.0172 (5)
C10	0.0449 (7)	0.0574 (7)	0.0560 (8)	−0.0177 (6)	0.0030 (6)	−0.0205 (6)
C11	0.0524 (9)	0.1224 (16)	0.0710 (11)	−0.0173 (10)	−0.0144 (8)	−0.0242 (11)
C12	0.0462 (7)	0.0483 (6)	0.0483 (7)	−0.0221 (5)	0.0060 (5)	−0.0136 (5)
C13	0.0499 (7)	0.0404 (6)	0.0446 (6)	−0.0181 (5)	0.0019 (5)	−0.0110 (5)
C14	0.0515 (7)	0.0568 (7)	0.0484 (7)	−0.0215 (6)	−0.0001 (6)	−0.0027 (6)
C15	0.0504 (8)	0.0629 (8)	0.0635 (9)	−0.0243 (7)	−0.0030 (6)	−0.0091 (7)
C16	0.0623 (9)	0.0521 (7)	0.0576 (8)	−0.0157 (6)	−0.0123 (7)	−0.0148 (6)
C17	0.0745 (10)	0.0535 (8)	0.0487 (7)	−0.0211 (7)	−0.0075 (7)	−0.0017 (6)
C18	0.0600 (8)	0.0490 (7)	0.0534 (8)	−0.0246 (6)	0.0010 (6)	−0.0029 (6)
C19	0.0806 (13)	0.1011 (15)	0.0808 (12)	−0.0241 (11)	−0.0337 (10)	−0.0105 (11)
N1	0.0485 (6)	0.0423 (5)	0.0524 (6)	−0.0168 (4)	0.0037 (5)	−0.0118 (5)
O1	0.0685 (7)	0.0460 (5)	0.0879 (8)	−0.0241 (5)	0.0180 (6)	−0.0223 (5)
O2	0.0513 (5)	0.0418 (4)	0.0421 (4)	−0.0193 (4)	0.0095 (4)	−0.0118 (3)
O3	0.0586 (7)	0.0883 (9)	0.1159 (11)	−0.0418 (6)	−0.0146 (7)	0.0059 (8)
O4	0.0507 (6)	0.1054 (9)	0.0517 (6)	−0.0264 (6)	−0.0068 (5)	−0.0074 (6)

C1—N1	1.2644 (16)	C11—H11B	0.9600
C1—C2	1.4602 (17)	C11—H11C	0.9600
C1—H1	0.9300	C12—C13	1.4566 (19)
C2—C3	1.3879 (17)	C12—H12	0.9300
C2—C7	1.4027 (16)	C13—C14	1.3902 (18)
C3—C4	1.378 (2)	C13—C18	1.3964 (18)
C3—H3	0.9300	C14—C15	1.378 (2)
C4—C5	1.377 (2)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.383 (2)
C5—C6	1.3815 (19)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.380 (2)
C6—C7	1.3860 (17)	C16—C19	1.506 (2)
C6—H6	0.9300	C17—C18	1.370 (2)
C7—O2	1.3618 (14)	C17—H17	0.9300
C8—O2	1.4386 (14)	C18—H18	0.9300
C8—C9	1.4925 (17)	C19—H19A	0.9600
C8—H8A	0.9700	C19—H19B	0.9600
C8—H8B	0.9700	C19—H19C	0.9600
C9—C12	1.3386 (18)	C19—H19D	0.9600
C9—C10	1.4886 (19)	C19—H19F	0.9600
C10—O3	1.1910 (17)	C19—H19E	0.9600
C10—O4	1.3336 (18)	N1—O1	1.4052 (14)
C11—O4	1.443 (2)	O1—H1A	0.8200
C11—H11A	0.9600
N1—C1—C2	120.89 (11)	H11A—C11—H11C	109.5
N1—C1—H1	119.6	H11B—C11—H11C	109.5
C2—C1—H1	119.6	C9—C12—C13	131.50 (12)
C3—C2—C7	118.50 (11)	C9—C12—H12	114.2
C3—C2—C1	122.09 (11)	C13—C12—H12	114.2
C7—C2—C1	119.40 (10)	C14—C13—C18	116.93 (13)
C4—C3—C2	121.16 (13)	C14—C13—C12	125.81 (12)
C4—C3—H3	119.4	C18—C13—C12	117.26 (12)
C2—C3—H3	119.4	C15—C14—C13	121.00 (13)
C5—C4—C3	119.61 (13)	C15—C14—H14	119.5
C5—C4—H4	120.2	C13—C14—H14	119.5
C3—C4—H4	120.2	C14—C15—C16	121.55 (14)
C4—C5—C6	120.81 (13)	C14—C15—H15	119.2
C4—C5—H5	119.6	C16—C15—H15	119.2
C6—C5—H5	119.6	C17—C16—C15	117.63 (14)
C5—C6—C7	119.55 (12)	C17—C16—C19	121.61 (15)
C5—C6—H6	120.2	C15—C16—C19	120.76 (16)
C7—C6—H6	120.2	C18—C17—C16	121.27 (14)
O2—C7—C6	124.60 (11)	C18—C17—H17	119.4
O2—C7—C2	115.05 (10)	C16—C17—H17	119.4
C6—C7—C2	120.35 (11)	C17—C18—C13	121.57 (14)
O2—C8—C9	107.57 (9)	C17—C18—H18	119.2
O2—C8—H8A	110.2	C13—C18—H18	119.2
C9—C8—H8A	110.2	C16—C19—H19A	109.5
O2—C8—H8B	110.2	C16—C19—H19B	109.5
C9—C8—H8B	110.2	C16—C19—H19C	109.5
H8A—C8—H8B	108.5	C16—C19—H19D	109.5
C12—C9—C10	115.91 (12)	C16—C19—H19F	109.5
C12—C9—C8	125.82 (12)	H19D—C19—H19F	109.5
C10—C9—C8	118.27 (11)	C16—C19—H19E	109.5
O3—C10—O4	122.75 (14)	H19D—C19—H19E	109.5
O3—C10—C9	125.04 (14)	H19F—C19—H19E	109.5
O4—C10—C9	112.19 (12)	C1—N1—O1	111.94 (11)
O4—C11—H11A	109.5	N1—O1—H1A	109.5
O4—C11—H11B	109.5	C7—O2—C8	118.77 (9)
H11A—C11—H11B	109.5	C10—O4—C11	116.22 (14)
O4—C11—H11C	109.5
N1—C1—C2—C3	−23.53 (19)	C8—C9—C12—C13	−0.6 (2)
N1—C1—C2—C7	157.62 (12)	C9—C12—C13—C14	20.6 (2)
C7—C2—C3—C4	−1.2 (2)	C9—C12—C13—C18	−159.99 (14)
C1—C2—C3—C4	179.93 (13)	C18—C13—C14—C15	2.5 (2)
C2—C3—C4—C5	0.2 (2)	C12—C13—C14—C15	−178.12 (13)
C3—C4—C5—C6	0.6 (2)	C13—C14—C15—C16	−0.9 (2)
C4—C5—C6—C7	−0.3 (2)	C14—C15—C16—C17	−1.0 (2)
C5—C6—C7—O2	179.27 (12)	C14—C15—C16—C19	178.59 (15)
C5—C6—C7—C2	−0.80 (19)	C15—C16—C17—C18	1.3 (2)
C3—C2—C7—O2	−178.54 (11)	C19—C16—C17—C18	−178.27 (15)
C1—C2—C7—O2	0.35 (16)	C16—C17—C18—C13	0.3 (2)
C3—C2—C7—C6	1.53 (17)	C14—C13—C18—C17	−2.2 (2)
C1—C2—C7—C6	−179.59 (11)	C12—C13—C18—C17	178.37 (13)
O2—C8—C9—C12	−82.19 (15)	C2—C1—N1—O1	178.81 (11)
O2—C8—C9—C10	97.89 (12)	C6—C7—O2—C8	0.84 (17)
C12—C9—C10—O3	−10.0 (2)	C2—C7—O2—C8	−179.09 (10)
C8—C9—C10—O3	169.98 (14)	C9—C8—O2—C7	−170.37 (10)
C12—C9—C10—O4	171.55 (12)	O3—C10—O4—C11	1.0 (2)
C8—C9—C10—O4	−8.52 (16)	C9—C10—O4—C11	179.55 (13)
C10—C9—C12—C13	179.32 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1i	0.82	2.11	2.8211 (15)	145
C15—H15···O3ii	0.93	2.40	3.247 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1i	0.82	2.11	2.8211 (15)	145
C15—H15⋯O3ii	0.93	2.40	3.247 (2)	151

Symmetry codes: (i) ; (ii) .