N-[(Z)-4-Meth-oxy-benzyl-idene](meth-oxy-carbon-yl)methanamine oxide.

The title compound, C(11)H(13)NO(4), contains a nitrone group, C=N-O-R, the geometry of which shows a Z configuration with near planarity (r.m.s. deviation = 0.0787 Å) around the C=N double bond. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal packing, mol-ecules are linked into R(2) (2)(12) dimers and R(2) (2)(14) rings via C-H⋯O inter-molecular hydrogen bonds.

Related literature

For the application and synthesis of nitro­nes, see: Merino (2004 ▶); Mocours et al. (1995 ▶); Frederickson (1997 ▶); Gothelf & Jorgensen (2000 ▶); Merino et al. (1998 ▶); McCaig et al. (1998 ▶); Desvergnes et al. (2005 ▶); Hanselmann et al. (2003 ▶); Pillard et al. (2007 ▶); Merino et al. (2008 ▶); Kobayashi et al. (2000 ▶). For the synthesis of the title compound, see: Diez-Martinez et al. (2010 ▶). For related structures, see: Bedford et al. (1991 ▶); Kliegel et al. (1998 ▶); Greci & Sgarabotto (1984 ▶); Christensen et al. (1990 ▶); Merino et al. (1996 ▶); Olszewski & Stadnicka (1995 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H13NO4

M = 223.22

Orthorhombic,

a = 4.3808 (3) Å

b = 9.8207 (7) Å

c = 25.7780 (17) Å

V = 1109.03 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.77 × 0.46 × 0.25 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.953, T max = 0.981

5112 measured reflections

1391 independent reflections

1053 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.082

S = 0.96

1391 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.09 e Å−3

Δρmin = −0.09 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536810032289/bv2158sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032289/bv2158Isup2.hkl

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

C11H13NO4	F(000) = 472
Mr = 223.22	Dx = 1.337 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5112 reflections
a = 4.3808 (3) Å	θ = 2.1–27.1°
b = 9.8207 (7) Å	µ = 0.10 mm−1
c = 25.7780 (17) Å	T = 296 K
V = 1109.03 (13) Å3	Prism, colourless
Z = 4	0.77 × 0.46 × 0.25 mm

Stoe IPDS II diffractometer	1391 independent reflections
Radiation source: fine-focus sealed tube	1053 reflections with I > 2σ(I)
graphite	Rint = 0.051
rotation method scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −5→5
Tmin = 0.953, Tmax = 0.981	k = −12→11
5112 measured reflections	l = −23→32

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0465P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
1391 reflections	Δρmax = 0.09 e Å−3
146 parameters	Δρmin = −0.09 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (4)

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	0.6012 (4)	0.7397 (2)	0.36104 (8)	0.0608 (5)
C2	0.5996 (5)	0.8775 (2)	0.34738 (10)	0.0734 (6)
H2	0.7092	0.9392	0.3674	0.088*
C3	0.4417 (6)	0.9235 (2)	0.30549 (11)	0.0808 (7)
H3	0.4449	1.0157	0.2973	0.097*
C4	0.2769 (5)	0.8343 (2)	0.27506 (10)	0.0700 (6)
C5	0.2692 (5)	0.6979 (2)	0.28817 (9)	0.0669 (6)
H5	0.1550	0.6373	0.2684	0.080*
C6	0.4307 (5)	0.6515 (2)	0.33055 (9)	0.0642 (5)
H6	0.4251	0.5594	0.3389	0.077*
C7	−0.0090 (7)	0.8031 (3)	0.19685 (11)	0.0960 (8)
H7A	−0.1660	0.7516	0.2139	0.115*
H7B	0.1394	0.7421	0.1824	0.115*
H7C	−0.0977	0.8568	0.1696	0.115*
C8	0.7873 (4)	0.7021 (2)	0.40462 (9)	0.0663 (6)
H8	0.8911	0.7726	0.4210	0.080*
C9	1.0392 (4)	0.5582 (3)	0.46700 (10)	0.0735 (6)
H9A	1.1358	0.6433	0.4767	0.088*
H9B	1.1972	0.4944	0.4568	0.088*
C10	0.8628 (4)	0.5022 (2)	0.51187 (9)	0.0651 (6)
C11	0.8063 (7)	0.3210 (2)	0.57071 (12)	0.0936 (8)
H11A	0.5973	0.3064	0.5610	0.112*
H11B	0.8145	0.3798	0.6004	0.112*
H11C	0.8999	0.2354	0.5790	0.112*
N1	0.8278 (3)	0.58064 (18)	0.42386 (7)	0.0635 (5)
O1	0.1341 (5)	0.88972 (18)	0.23310 (7)	0.0935 (5)
O2	0.6925 (3)	0.47139 (14)	0.40781 (7)	0.0756 (4)
O3	0.6482 (4)	0.55930 (17)	0.53126 (7)	0.0837 (5)
O4	0.9683 (3)	0.38384 (16)	0.52795 (7)	0.0818 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0565 (10)	0.0555 (12)	0.0703 (14)	−0.0055 (9)	0.0131 (10)	−0.0071 (10)
C2	0.0762 (13)	0.0549 (13)	0.0892 (17)	−0.0113 (11)	0.0137 (13)	−0.0082 (12)
C3	0.0940 (15)	0.0523 (13)	0.0962 (18)	−0.0079 (12)	0.0194 (15)	−0.0010 (13)
C4	0.0741 (12)	0.0629 (14)	0.0728 (15)	0.0046 (11)	0.0182 (11)	0.0054 (11)
C5	0.0696 (12)	0.0591 (12)	0.0720 (16)	−0.0034 (10)	0.0081 (11)	−0.0023 (10)
C6	0.0685 (11)	0.0501 (11)	0.0741 (14)	−0.0057 (9)	0.0072 (11)	−0.0025 (10)
C7	0.1023 (18)	0.098 (2)	0.0877 (18)	0.0114 (18)	−0.0029 (17)	0.0066 (15)
C8	0.0579 (10)	0.0614 (12)	0.0794 (15)	−0.0110 (10)	0.0088 (11)	−0.0134 (11)
C9	0.0527 (9)	0.0765 (15)	0.0913 (16)	0.0053 (10)	−0.0047 (12)	−0.0109 (12)
C10	0.0557 (9)	0.0672 (13)	0.0725 (14)	0.0086 (10)	−0.0106 (10)	−0.0172 (11)
C11	0.1051 (17)	0.0735 (16)	0.102 (2)	0.0058 (15)	−0.0075 (17)	0.0015 (14)
N1	0.0534 (7)	0.0632 (11)	0.0740 (12)	−0.0055 (8)	0.0053 (8)	−0.0128 (9)
O1	0.1121 (12)	0.0784 (11)	0.0898 (12)	0.0083 (11)	0.0037 (11)	0.0148 (10)
O2	0.0860 (9)	0.0599 (9)	0.0809 (10)	−0.0109 (8)	−0.0067 (9)	−0.0087 (7)
O3	0.0827 (9)	0.0877 (11)	0.0806 (11)	0.0308 (9)	0.0081 (9)	−0.0077 (9)
O4	0.0730 (8)	0.0676 (10)	0.1048 (12)	0.0181 (8)	0.0022 (9)	−0.0034 (9)

C1—C6	1.388 (3)	C7—H7C	0.9600
C1—C2	1.399 (3)	C8—N1	1.304 (3)
C1—C8	1.436 (3)	C8—H8	0.9300
C2—C3	1.359 (4)	C9—N1	1.464 (3)
C2—H2	0.9300	C9—C10	1.496 (3)
C3—C4	1.380 (3)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—O1	1.363 (3)	C10—O3	1.203 (2)
C4—C5	1.382 (3)	C10—O4	1.318 (3)
C5—C6	1.379 (3)	C11—O4	1.449 (3)
C5—H5	0.9300	C11—H11A	0.9600
C6—H6	0.9300	C11—H11B	0.9600
C7—O1	1.410 (3)	C11—H11C	0.9600
C7—H7A	0.9600	N1—O2	1.294 (2)
C7—H7B	0.9600
C6—C1—C2	117.3 (2)	N1—C8—C1	127.57 (19)
C6—C1—C8	126.0 (2)	N1—C8—H8	116.2
C2—C1—C8	116.64 (19)	C1—C8—H8	116.2
C3—C2—C1	121.6 (2)	N1—C9—C10	108.42 (15)
C3—C2—H2	119.2	N1—C9—H9A	110.0
C1—C2—H2	119.2	C10—C9—H9A	110.0
C2—C3—C4	120.5 (2)	N1—C9—H9B	110.0
C2—C3—H3	119.8	C10—C9—H9B	110.0
C4—C3—H3	119.8	H9A—C9—H9B	108.4
O1—C4—C5	124.8 (2)	O3—C10—O4	123.7 (2)
O1—C4—C3	116.0 (2)	O3—C10—C9	123.6 (2)
C5—C4—C3	119.3 (2)	O4—C10—C9	112.71 (18)
C4—C5—C6	120.1 (2)	O4—C11—H11A	109.5
C4—C5—H5	120.0	O4—C11—H11B	109.5
C6—C5—H5	120.0	H11A—C11—H11B	109.5
C5—C6—C1	121.3 (2)	O4—C11—H11C	109.5
C5—C6—H6	119.4	H11A—C11—H11C	109.5
C1—C6—H6	119.4	H11B—C11—H11C	109.5
O1—C7—H7A	109.5	O2—N1—C8	125.08 (18)
O1—C7—H7B	109.5	O2—N1—C9	114.05 (17)
H7A—C7—H7B	109.5	C8—N1—C9	120.86 (17)
O1—C7—H7C	109.5	C4—O1—C7	119.3 (2)
H7A—C7—H7C	109.5	C10—O4—C11	116.31 (17)
H7B—C7—H7C	109.5
C6—C1—C2—C3	−1.0 (3)	C2—C1—C8—N1	−179.0 (2)
C8—C1—C2—C3	177.2 (2)	N1—C9—C10—O3	−57.6 (3)
C1—C2—C3—C4	0.1 (3)	N1—C9—C10—O4	122.64 (18)
C2—C3—C4—O1	−178.1 (2)	C1—C8—N1—O2	−3.3 (3)
C2—C3—C4—C5	1.2 (3)	C1—C8—N1—C9	176.68 (18)
O1—C4—C5—C6	177.8 (2)	C10—C9—N1—O2	−60.8 (2)
C3—C4—C5—C6	−1.5 (3)	C10—C9—N1—C8	119.2 (2)
C4—C5—C6—C1	0.5 (3)	C5—C4—O1—C7	−6.6 (3)
C2—C1—C6—C5	0.7 (3)	C3—C4—O1—C7	172.7 (2)
C8—C1—C6—C5	−177.30 (19)	O3—C10—O4—C11	1.4 (3)
C6—C1—C8—N1	−0.9 (3)	C9—C10—O4—C11	−178.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.30	2.900 (3)	122
C8—H8···O3i	0.93	2.35	3.275 (3)	175
C9—H9B···O2ii	0.97	2.52	3.353 (3)	144
C11—H11C···O2iii	0.96	2.43	3.379 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2	0.93	2.30	2.900 (3)	122
C8—H8⋯O3i	0.93	2.35	3.275 (3)	175
C9—H9B⋯O2ii	0.97	2.52	3.353 (3)	144
C11—H11C⋯O2iii	0.96	2.43	3.379 (3)	172

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