4-Nitro-phenyl methacrylate.

The title compound, C(10)H(9)NO(4), was obtained serendipitously during the preparation of benzyl cyclo-hexyl-carbamate. The mol-ecule consists of two approximately planar parts, the nitro-phenyl ring and the rest of the non-H atoms, with a dihedral angle of 55.05 (6)° between the two segments. The crystal structure is stabilized by weak C-H⋯O inter-actions and π stacking [3.753 (1) Å] along the b axis.

Related literature

For related literature, see: Banks et al. (1977 ▶); Hwang et al. (2007 ▶); Li et al. (2007 ▶); Otsu et al. (1968 ▶); Tang et al. (2007 ▶).

Experimental

Crystal data

C10H9NO4

M = 207.18

Monoclinic,

a = 24.491 (6) Å

b = 3.753 (1) Å

c = 23.428 (6) Å

β = 116.98 (1)°

V = 1919.0 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 90.0 (2) K

0.30 × 0.10 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.967, T max = 0.996

3936 measured reflections

2193 independent reflections

1380 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.145

S = 1.04

2193 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.28 e Å−3

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025130/fl2212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025130/fl2212Isup2.hkl

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

C10H9NO4	F000 = 864
Mr = 207.18	Dx = 1.434 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
a = 24.491 (6) Å	Cell parameters from 2523 reflections
b = 3.753 (1) Å	θ = 1.0–27.5º
c = 23.428 (6) Å	µ = 0.11 mm−1
β = 116.98 (1)º	T = 90.0 (2) K
V = 1919.0 (9) Å3	Thin rod, colorless
Z = 8	0.30 × 0.10 × 0.04 mm

Nonius KappaCCD diffractometer	2193 independent reflections
Radiation source: fine-focus sealed tube	1380 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.049
Detector resolution: 18 pixels mm-1	θmax = 27.5º
T = 90.0(2) K	θmin = 1.9º
ω scans at fixed χ = 55°	h = −31→31
Absorption correction: multi-scan(SCALEPACK; Otwinowski & Minor, 1997)	k = −4→4
Tmin = 0.967, Tmax = 0.996	l = −30→29
3936 measured reflections

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0788P)2 + 0.0268P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2193 reflections	Δρmax = 0.32 e Å−3
137 parameters	Δρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.34238 (9)	0.3043 (6)	0.08125 (9)	0.0350 (5)
H1A	0.3022	0.2636	0.0481	0.042*
H1B	0.3769	0.2388	0.0753	0.042*
C2	0.41131 (8)	0.5324 (6)	0.19114 (9)	0.0327 (5)
H2A	0.4437	0.4551	0.1803	0.049*
H2B	0.4153	0.4042	0.2293	0.049*
H2C	0.4150	0.7891	0.1998	0.049*
C3	0.35044 (8)	0.4545 (6)	0.13665 (9)	0.0258 (5)
C4	0.29729 (8)	0.5595 (5)	0.14726 (9)	0.0247 (5)
C5	0.18934 (8)	0.4978 (5)	0.10638 (9)	0.0232 (5)
C6	0.18535 (8)	0.3892 (5)	0.16081 (8)	0.0248 (5)
H6	0.2196	0.2858	0.1958	0.030*
C7	0.13046 (8)	0.4341 (5)	0.16321 (9)	0.0249 (5)
H7	0.1262	0.3607	0.1998	0.030*
C8	0.08165 (8)	0.5879 (5)	0.11143 (8)	0.0225 (5)
C9	0.08549 (8)	0.6948 (5)	0.05692 (8)	0.0239 (5)
H9	0.0511	0.7963	0.0218	0.029*
C10	0.14063 (8)	0.6505 (5)	0.05472 (8)	0.0243 (5)
H10	0.1449	0.7242	0.0182	0.029*
N1	0.02377 (7)	0.6382 (5)	0.11468 (7)	0.0273 (4)
O1	0.30028 (5)	0.7338 (4)	0.19146 (6)	0.0309 (4)
O2	0.24257 (5)	0.4394 (4)	0.09952 (6)	0.0265 (4)
O3	0.01867 (6)	0.5094 (4)	0.16001 (7)	0.0379 (4)
O4	−0.01732 (6)	0.8076 (4)	0.07152 (6)	0.0356 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0292 (11)	0.0418 (15)	0.0387 (11)	−0.0006 (11)	0.0195 (9)	−0.0047 (11)
C2	0.0274 (11)	0.0333 (14)	0.0390 (12)	0.0015 (10)	0.0165 (10)	−0.0001 (10)
C3	0.0258 (10)	0.0259 (12)	0.0286 (11)	−0.0004 (9)	0.0148 (9)	0.0030 (9)
C4	0.0239 (10)	0.0250 (12)	0.0228 (10)	0.0004 (9)	0.0084 (8)	0.0007 (9)
C5	0.0217 (10)	0.0231 (12)	0.0272 (10)	−0.0010 (9)	0.0133 (8)	−0.0051 (9)
C6	0.0215 (10)	0.0237 (12)	0.0246 (10)	−0.0001 (9)	0.0066 (8)	−0.0014 (9)
C7	0.0258 (10)	0.0254 (12)	0.0238 (10)	−0.0008 (9)	0.0116 (8)	−0.0005 (8)
C8	0.0199 (9)	0.0233 (12)	0.0251 (10)	−0.0017 (9)	0.0107 (8)	−0.0032 (9)
C9	0.0230 (10)	0.0233 (12)	0.0219 (9)	0.0006 (9)	0.0070 (8)	−0.0013 (9)
C10	0.0269 (10)	0.0248 (12)	0.0204 (9)	0.0004 (9)	0.0102 (8)	−0.0007 (9)
N1	0.0238 (9)	0.0312 (11)	0.0268 (9)	0.0008 (8)	0.0113 (7)	−0.0005 (8)
O1	0.0260 (7)	0.0375 (10)	0.0295 (7)	−0.0029 (7)	0.0129 (6)	−0.0088 (7)
O2	0.0201 (7)	0.0343 (8)	0.0258 (7)	−0.0005 (6)	0.0111 (6)	−0.0043 (6)
O3	0.0317 (8)	0.0518 (11)	0.0365 (8)	0.0040 (7)	0.0210 (7)	0.0094 (7)
O4	0.0251 (7)	0.0489 (11)	0.0319 (7)	0.0098 (7)	0.0121 (6)	0.0059 (7)

C1—C3	1.345 (3)	C5—O2	1.402 (2)
C1—H1A	0.9500	C6—C7	1.381 (3)
C1—H1B	0.9500	C6—H6	0.9500
C2—C3	1.487 (2)	C7—C8	1.385 (3)
C2—H2A	0.9800	C7—H7	0.9500
C2—H2B	0.9800	C8—C9	1.382 (2)
C2—H2C	0.9800	C8—N1	1.466 (2)
C3—C4	1.485 (3)	C9—C10	1.385 (3)
C4—O1	1.199 (2)	C9—H9	0.9500
C4—O2	1.375 (2)	C10—H10	0.9500
C5—C10	1.381 (3)	N1—O3	1.224 (2)
C5—C6	1.384 (3)	N1—O4	1.231 (2)
C3—C1—H1A	120.0	C7—C6—H6	120.7
C3—C1—H1B	120.0	C5—C6—H6	120.7
H1A—C1—H1B	120.0	C6—C7—C8	119.00 (17)
C3—C2—H2A	109.5	C6—C7—H7	120.5
C3—C2—H2B	109.5	C8—C7—H7	120.5
H2A—C2—H2B	109.5	C9—C8—C7	122.47 (17)
C3—C2—H2C	109.5	C9—C8—N1	118.91 (16)
H2A—C2—H2C	109.5	C7—C8—N1	118.62 (16)
H2B—C2—H2C	109.5	C8—C9—C10	118.42 (17)
C1—C3—C4	121.11 (17)	C8—C9—H9	120.8
C1—C3—C2	124.19 (18)	C10—C9—H9	120.8
C4—C3—C2	114.70 (17)	C5—C10—C9	119.11 (17)
O1—C4—O2	122.47 (17)	C5—C10—H10	120.4
O1—C4—C3	125.08 (17)	C9—C10—H10	120.4
O2—C4—C3	112.45 (16)	O3—N1—O4	123.34 (16)
C10—C5—C6	122.41 (17)	O3—N1—C8	118.44 (15)
C10—C5—O2	116.30 (16)	O4—N1—C8	118.22 (15)
C6—C5—O2	121.19 (16)	C4—O2—C5	118.00 (14)
C7—C6—C5	118.58 (17)
C1—C3—C4—O1	−170.1 (2)	C6—C5—C10—C9	−0.5 (3)
C2—C3—C4—O1	9.4 (3)	O2—C5—C10—C9	176.01 (16)
C1—C3—C4—O2	8.8 (3)	C8—C9—C10—C5	0.8 (3)
C2—C3—C4—O2	−171.74 (17)	C9—C8—N1—O3	172.43 (18)
C10—C5—C6—C7	0.3 (3)	C7—C8—N1—O3	−7.5 (3)
O2—C5—C6—C7	−176.06 (18)	C9—C8—N1—O4	−7.5 (3)
C5—C6—C7—C8	−0.4 (3)	C7—C8—N1—O4	172.65 (18)
C6—C7—C8—C9	0.8 (3)	O1—C4—O2—C5	−5.8 (3)
C6—C7—C8—N1	−179.34 (17)	C3—C4—O2—C5	175.30 (15)
C7—C8—C9—C10	−1.0 (3)	C10—C5—O2—C4	129.61 (19)
N1—C8—C9—C10	179.14 (16)	C6—C5—O2—C4	−53.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.95	2.41	3.130 (2)	133
C1—H1B···O4ii	0.95	2.64	3.546 (3)	159
C2—H2A···O3ii	0.98	2.68	3.611 (2)	159
C9—H9···O4iii	0.95	2.46	3.282 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.95	2.41	3.130 (2)	133
C1—H1B⋯O4ii	0.95	2.64	3.546 (3)	159
C2—H2A⋯O3ii	0.98	2.68	3.611 (2)	159
C9—H9⋯O4iii	0.95	2.46	3.282 (2)	145

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