2-Methyl-3-(4-nitro-phen-yl)acrylic acid.

The title compound, C(10)H(9)NO(4), forms R(2) (2)(8) dimers due to inter-molecular O-H⋯O hydrogen bonding in the crystal structure. Two dimers are further linked to each other through two inter-molecular C-H⋯O hydrogen bonds, forming an R(3) (3)(7) ring motif. The nitro groups form an intra-molecular C-H⋯O hydrogen bond mimicking a five-membered ring. As a result of these hydrogen bonds, polymeric sheets are formed. The aromatic ring makes a dihedral angle of 42.84 (8)° with the carboxyl-ate group and an angle of 8.01 (14)° with the nitro group. There is a π-inter-action (N-O⋯π) between the nitro group and the aromatic ring, with a distance of 3.7572 (14) Å between the N atom and the centroid of the aromatic ring.

Related literature

For related literature, see: Bernstein et al. (1995 ▶); Fujii et al. (2002 ▶); Ma & Hayes (2004 ▶); Muhammad et al. (2007 ▶, 2008a ▶,b ▶); Muhammad, Ali, Tahir & Zia-ur-n class="Chemical">Rehman (2008 ▶); Muhammad, Tahir, Ali, Zia-ur-Rehman & Kashmiri (2008 ▶); Muhammad, Tahir, Zia-ur-Rehman & Ali (2008 ▶); Muhammad, Tahir, Zia-ur-Rehman, Ali & Shaheen, 2008 ▶); Niaz et al. (2008 ▶).

Experimental

Crystal data

C10H9NO4

M = 207.18

Triclinic,

a = 7.3878 (3) Å

b = 8.1050 (5) Å

c = 8.3402 (4) Å

α = 75.793 (2)°

β = 81.835 (3)°

γ = 87.686 (2)°

V = 479.21 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 (2) K

0.25 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.970, T max = 0.981

9039 measured reflections

2518 independent reflections

1926 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.134

S = 1.02

2518 reflections

140 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024999/cs2087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024999/cs2087Isup2.hkl

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

C10H9NO4	Z = 2
Mr = 207.18	F000 = 216
Triclinic, P1	Dx = 1.436 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.3878 (3) Å	Cell parameters from 2518 reflections
b = 8.1050 (5) Å	θ = 2.5–29.1º
c = 8.3402 (4) Å	µ = 0.11 mm−1
α = 75.793 (2)º	T = 296 (2) K
β = 81.835 (3)º	Prismatic, colourless
γ = 87.686 (2)º	0.25 × 0.20 × 0.18 mm
V = 479.21 (4) Å3

Bruker Kappa APEXII CCD diffractometer	2518 independent reflections
Radiation source: fine-focus sealed tube	1926 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
Detector resolution: 7.4 pixels mm-1	θmax = 29.1º
T = 296(2) K	θmin = 2.5º
ω scans	h = −10→9
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −11→9
Tmin = 0.970, Tmax = 0.981	l = −11→11
9039 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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.0915P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2518 reflections	Δρmax = 0.24 e Å−3
140 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction coefficient: ?

	x	y	z	Uiso*/Ueq
O1	0.04661 (16)	0.13519 (13)	0.29456 (12)	0.0547 (4)
O2	0.09796 (15)	0.16087 (12)	0.54300 (12)	0.0526 (3)
O3	0.52309 (18)	1.11600 (15)	−0.36244 (14)	0.0661 (4)
O4	0.35761 (19)	1.23296 (13)	−0.18699 (15)	0.0648 (4)
N1	0.41247 (18)	1.10856 (14)	−0.23745 (14)	0.0466 (4)
C1	0.10453 (16)	0.21896 (15)	0.39150 (15)	0.0357 (3)
C2	0.17797 (17)	0.39231 (15)	0.31101 (16)	0.0362 (3)
C3	0.17195 (18)	0.45348 (15)	0.14759 (16)	0.0378 (3)
C4	0.22936 (17)	0.62471 (15)	0.04743 (15)	0.0361 (3)
C5	0.3308 (2)	0.64219 (16)	−0.11015 (16)	0.0424 (4)
C6	0.39099 (19)	0.80039 (17)	−0.20464 (16)	0.0425 (4)
C7	0.34487 (18)	0.94026 (15)	−0.14089 (15)	0.0375 (4)
C8	0.2375 (2)	0.92912 (16)	0.01030 (17)	0.0432 (4)
C9	0.1804 (2)	0.76957 (16)	0.10462 (16)	0.0430 (4)
C10	0.2580 (2)	0.47901 (17)	0.42356 (17)	0.0480 (4)
H1	−0.005 (3)	0.032 (3)	0.355 (2)	0.0656*
H3	0.12727	0.38114	0.09157	0.0454*
H5	0.35821	0.54652	−0.15208	0.0508*
H6	0.46089	0.81202	−0.30868	0.0510*
H8	0.20402	1.02624	0.04821	0.0518*
H9	0.10844	0.75935	0.20750	0.0516*
H10A	0.33667	0.40104	0.48836	0.0719*
H10B	0.16126	0.51574	0.49695	0.0719*
H10C	0.32723	0.57588	0.35757	0.0719*

	U11	U22	U33	U12	U13	U23
O1	0.0855 (8)	0.0371 (5)	0.0397 (5)	−0.0259 (5)	−0.0071 (5)	−0.0026 (4)
O2	0.0801 (7)	0.0381 (5)	0.0357 (5)	−0.0229 (5)	−0.0058 (5)	0.0008 (4)
O3	0.0862 (8)	0.0524 (7)	0.0487 (6)	−0.0249 (6)	0.0068 (6)	0.0033 (5)
O4	0.1010 (9)	0.0290 (5)	0.0614 (7)	−0.0085 (5)	−0.0120 (6)	−0.0036 (5)
N1	0.0638 (7)	0.0340 (6)	0.0385 (6)	−0.0119 (5)	−0.0133 (5)	0.0030 (5)
C1	0.0399 (6)	0.0288 (6)	0.0353 (6)	−0.0057 (5)	−0.0021 (5)	−0.0028 (4)
C2	0.0379 (6)	0.0278 (5)	0.0392 (6)	−0.0052 (5)	−0.0024 (5)	−0.0019 (5)
C3	0.0443 (6)	0.0284 (6)	0.0380 (6)	−0.0068 (5)	−0.0037 (5)	−0.0029 (5)
C4	0.0416 (6)	0.0294 (6)	0.0342 (6)	−0.0041 (5)	−0.0064 (5)	−0.0004 (4)
C5	0.0569 (8)	0.0300 (6)	0.0375 (6)	−0.0005 (5)	−0.0009 (5)	−0.0062 (5)
C6	0.0521 (7)	0.0360 (6)	0.0338 (6)	−0.0020 (5)	0.0023 (5)	−0.0023 (5)
C7	0.0468 (7)	0.0281 (6)	0.0343 (6)	−0.0062 (5)	−0.0093 (5)	0.0017 (5)
C8	0.0607 (8)	0.0292 (6)	0.0380 (6)	0.0016 (5)	−0.0052 (6)	−0.0062 (5)
C9	0.0554 (8)	0.0348 (6)	0.0334 (6)	−0.0009 (5)	0.0030 (5)	−0.0029 (5)
C10	0.0626 (8)	0.0353 (7)	0.0437 (7)	−0.0160 (6)	−0.0124 (6)	0.0001 (5)

O1—C1	1.2996 (16)	C5—C6	1.3832 (19)
O2—C1	1.2300 (15)	C6—C7	1.3774 (19)
O3—N1	1.2204 (17)	C7—C8	1.3759 (19)
O4—N1	1.2185 (16)	C8—C9	1.3855 (19)
O1—H1	0.93 (2)	C3—H3	0.9300
N1—C7	1.4698 (17)	C5—H5	0.9300
C1—C2	1.4880 (18)	C6—H6	0.9300
C2—C3	1.3376 (18)	C8—H8	0.9300
C2—C10	1.4965 (19)	C9—H9	0.9300
C3—C4	1.4770 (18)	C10—H10A	0.9600
C4—C9	1.3887 (18)	C10—H10B	0.9600
C4—C5	1.3951 (18)	C10—H10C	0.9600
O1···C8i	3.3471 (17)	C4···H10C	2.7200
O1···C6ii	3.4128 (19)	C4···H3ii	3.0300
O1···O2iii	2.6333 (15)	C9···H10C	2.6400
O2···O1iii	2.6333 (15)	C10···H9	2.8300
O2···C1iii	3.3657 (16)	C10···H10Bv	3.0700
O2···N1iv	3.1112 (17)	H1···O1iii	2.882 (17)
O1···H1iii	2.882 (17)	H1···O2iii	1.71 (2)
O1···H3	2.3100	H1···C1iii	2.59 (2)
O1···H8i	2.5500	H1···H1iii	2.36 (2)
O2···H10B	2.8600	H3···O1	2.3100
O2···H10A	2.5900	H3···H5	2.5900
O2···H1iii	1.71 (2)	H3···C4ii	3.0300
O2···H9v	2.6000	H5···O4i	2.6300
O3···H6	2.4400	H5···H3	2.5900
O3···H10Avi	2.7600	H6···O3	2.4400
O3···H6vii	2.6500	H6···O3vii	2.6500
O3···H10Cviii	2.7800	H6···C2x	3.0800
O4···H5ix	2.6300	H8···O1ix	2.5500
O4···H8	2.4200	H8···O4	2.4200
O4···H10Avi	2.7400	H9···C2	2.9300
O4···H10Cviii	2.8500	H9···C10	2.8300
N1···O2vi	3.1112 (17)	H9···H10C	2.4200
N1···C8viii	3.378 (2)	H9···O2v	2.6000
C1···O2iii	3.3657 (16)	H10A···O2	2.5900
C2···C6x	3.5837 (19)	H10A···O3iv	2.7600
C6···O1ii	3.4128 (19)	H10A···O4iv	2.7400
C6···C2x	3.5837 (19)	H10B···O2	2.8600
C8···N1viii	3.378 (2)	H10B···C1v	3.0800
C8···O1ix	3.3471 (17)	H10B···C2v	2.9500
C9···C10	3.1937 (19)	H10B···C10v	3.0700
C10···C9	3.1937 (19)	H10B···H10Bv	2.4000
C1···H10Bv	3.0800	H10C···C4	2.7200
C1···H1iii	2.59 (2)	H10C···C9	2.6400
C2···H9	2.9300	H10C···H9	2.4200
C2···H10Bv	2.9500	H10C···O3viii	2.7800
C2···H6x	3.0800	H10C···O4viii	2.8500
C1—O1—H1	111.6 (12)	C7—C8—C9	118.33 (12)
O3—N1—O4	123.45 (13)	C4—C9—C8	120.81 (12)
O3—N1—C7	118.21 (12)	C2—C3—H3	117.00
O4—N1—C7	118.33 (12)	C4—C3—H3	117.00
O1—C1—O2	122.55 (12)	C4—C5—H5	120.00
O1—C1—C2	116.77 (11)	C6—C5—H5	120.00
O2—C1—C2	120.68 (11)	C5—C6—H6	121.00
C1—C2—C10	115.28 (11)	C7—C6—H6	121.00
C3—C2—C10	126.40 (12)	C7—C8—H8	121.00
C1—C2—C3	118.29 (11)	C9—C8—H8	121.00
C2—C3—C4	126.35 (12)	C4—C9—H9	120.00
C3—C4—C9	121.47 (11)	C8—C9—H9	120.00
C5—C4—C9	119.09 (12)	C2—C10—H10A	109.00
C3—C4—C5	119.41 (11)	C2—C10—H10B	109.00
C4—C5—C6	120.66 (12)	C2—C10—H10C	109.00
C5—C6—C7	118.38 (12)	H10A—C10—H10B	109.00
N1—C7—C6	119.04 (11)	H10A—C10—H10C	110.00
N1—C7—C8	118.35 (11)	H10B—C10—H10C	109.00
C6—C7—C8	122.61 (12)
O3—N1—C7—C6	−7.7 (2)	C2—C3—C4—C9	−44.9 (2)
O3—N1—C7—C8	172.34 (13)	C3—C4—C5—C6	−178.09 (13)
O4—N1—C7—C6	173.58 (14)	C9—C4—C5—C6	3.7 (2)
O4—N1—C7—C8	−6.4 (2)	C3—C4—C9—C8	179.06 (13)
O1—C1—C2—C3	3.07 (18)	C5—C4—C9—C8	−2.7 (2)
O1—C1—C2—C10	−174.99 (12)	C4—C5—C6—C7	−1.4 (2)
O2—C1—C2—C3	−176.04 (13)	C5—C6—C7—N1	178.15 (13)
O2—C1—C2—C10	5.90 (18)	C5—C6—C7—C8	−1.9 (2)
C1—C2—C3—C4	176.84 (12)	N1—C7—C8—C9	−177.24 (13)
C10—C2—C3—C4	−5.3 (2)	C6—C7—C8—C9	2.8 (2)
C2—C3—C4—C5	136.88 (15)	C7—C8—C9—C4	−0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2iii	0.93 (2)	1.71 (2)	2.6333 (15)	177 (2)
C3—H3···O1	0.93	2.31	2.7080 (17)	105
C8—H8···O1ix	0.93	2.55	3.3471 (17)	144
C9—H9···O2v	0.93	2.60	3.4912 (17)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.93 (2)	1.71 (2)	2.6333 (15)	177 (2)
C3—H3⋯O1	0.93	2.31	2.7080 (17)	105
C8—H8⋯O1ii	0.93	2.55	3.3471 (17)	144
C9—H9⋯O2iii	0.93	2.60	3.4912 (17)	161

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