2-Methyl-2-(4-nitro-phen-oxy)propanoic acid.

The title compound, C(10)H(11)NO(5), is of inter-est with respect to its anti-dyslipidemic activity. It was prepared by reaction of 4-nitro-phenol with ethyl 2-bromo-2-methyl-propionate followed by ethyl ester hydrolysis. In the crystal, mol-ecules are linked into centrosymmetric dimers by inter-molecular O-H⋯O hydrogen bonds and the dimers are connected into chains by weak C-H⋯O inter-actions. The packing is further stabilized by offset π-π inter-actions between adjacent benzene rings with a centroid-centroid distance of 3.8643 (17) Å.

Related literature

For related literature on fibrate structures and hypolipidemic activity, see: Navarrete-Vázquez et al. (2008 ▶); Henry et al. (2003 ▶); Rath et al. (2005 ▶); Djinović et al. (1989 ▶); Thorp (1962 ▶); Thorp & Waring (1962 ▶); Miller & Spence (1998 ▶); Forcheron et al. (2002 ▶). For details of the graph-set analysis of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶)

Experimental

Crystal data

C10H11NO5

M = 225.20

Monoclinic,

a = 21.296 (3) Å

b = 7.0348 (9) Å

c = 14.518 (2) Å

β = 93.794 (2)°

V = 2170.2 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 294 (2) K

0.32 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.763, T max = 0.978

10072 measured reflections

1920 independent reflections

1745 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.163

S = 1.12

1920 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus-NT (Bruker, 2001 ▶); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶) and publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035411/sj2550sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035411/sj2550Isup2.hkl

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

C10H11NO5	F000 = 944
Mr = 225.20	Dx = 1.378 Mg m−3
Monoclinic, C2/c	Melting point: 396 K
Hall symbol: -C 2yc	Mo Kα radiation λ = 0.71073 Å
a = 21.296 (3) Å	Cell parameters from 5496 reflections
b = 7.0348 (9) Å	θ = 2.5–2.9º
c = 14.518 (2) Å	µ = 0.11 mm−1
β = 93.794 (2)º	T = 294 (2) K
V = 2170.2 (5) Å3	Prism, colourless
Z = 8	0.32 × 0.25 × 0.20 mm

Bruker SMART APEX CCD area-detector diffractometer	1920 independent reflections
Radiation source: fine-focus sealed tube	1745 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
T = 294(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −25→25
Tmin = 0.763, Tmax = 0.978	k = −8→8
10072 measured reflections	l = −17→17

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.065	w = 1/[σ2(Fo2) + (0.0689P)2 + 2.0562P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.163	(Δ/σ)max < 0.001
S = 1.12	Δρmax = 0.23 e Å−3
1920 reflections	Δρmin = −0.22 e Å−3
152 parameters	Extinction correction: SHELXTL-NT (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (2)
Secondary atom site location: difference Fourier map

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	0.43849 (11)	0.9257 (3)	0.38604 (15)	0.0513 (6)
C2	0.42396 (12)	0.7351 (4)	0.3768 (2)	0.0696 (8)
H2	0.3822	0.6954	0.3747	0.084*
C3	0.47162 (13)	0.6040 (4)	0.3706 (2)	0.0783 (9)
H3	0.4623	0.4754	0.3641	0.094*
C4	0.53299 (12)	0.6654 (4)	0.3741 (2)	0.0667 (7)
C5	0.54791 (12)	0.8533 (4)	0.38383 (19)	0.0661 (7)
H5	0.5897	0.8926	0.3866	0.079*
C6	0.50077 (11)	0.9819 (4)	0.38940 (18)	0.0613 (7)
H6	0.5106	1.1103	0.3956	0.074*
C7	0.33120 (11)	1.0562 (4)	0.36820 (17)	0.0584 (7)
C8	0.29840 (10)	0.9120 (3)	0.42697 (16)	0.0532 (6)
C9	0.30573 (14)	1.2523 (4)	0.3905 (2)	0.0801 (9)
H9A	0.3183	1.2844	0.4533	0.120*
H9B	0.2606	1.2512	0.3823	0.120*
H9C	0.3222	1.3448	0.3499	0.120*
C10	0.32173 (14)	1.0132 (5)	0.26611 (19)	0.0772 (8)
H10A	0.3449	1.1033	0.2320	0.116*
H10B	0.2778	1.0221	0.2471	0.116*
H10C	0.3365	0.8871	0.2544	0.116*
H5A	0.2918 (16)	0.838 (5)	0.547 (3)	0.101 (11)*
N1	0.58387 (13)	0.5287 (4)	0.3648 (2)	0.0966 (9)
O1	0.57049 (14)	0.3662 (4)	0.3469 (3)	0.1713 (19)
O2	0.63689 (12)	0.5842 (4)	0.3687 (3)	0.1449 (13)
O3	0.39722 (7)	1.0706 (2)	0.39675 (12)	0.0594 (5)
O4	0.25911 (8)	0.8033 (3)	0.39279 (12)	0.0711 (6)
O5	0.31446 (10)	0.9212 (3)	0.51375 (13)	0.0770 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0472 (12)	0.0552 (14)	0.0519 (13)	−0.0041 (10)	0.0076 (9)	0.0040 (10)
C2	0.0477 (13)	0.0595 (16)	0.103 (2)	−0.0087 (12)	0.0140 (13)	0.0028 (14)
C3	0.0658 (17)	0.0506 (15)	0.121 (2)	−0.0042 (13)	0.0250 (16)	0.0062 (15)
C4	0.0515 (14)	0.0686 (17)	0.0816 (18)	0.0059 (13)	0.0163 (12)	0.0123 (14)
C5	0.0453 (13)	0.0758 (18)	0.0784 (17)	−0.0102 (13)	0.0142 (12)	−0.0012 (14)
C6	0.0536 (14)	0.0583 (14)	0.0736 (16)	−0.0112 (12)	0.0151 (11)	−0.0034 (12)
C7	0.0481 (13)	0.0609 (15)	0.0659 (15)	0.0001 (11)	0.0021 (10)	0.0060 (12)
C8	0.0418 (11)	0.0595 (14)	0.0583 (14)	0.0012 (10)	0.0025 (10)	−0.0016 (11)
C9	0.0691 (17)	0.0653 (17)	0.106 (2)	0.0078 (14)	0.0085 (15)	0.0093 (16)
C10	0.0730 (18)	0.092 (2)	0.0657 (17)	−0.0098 (16)	0.0012 (13)	0.0144 (15)
N1	0.0659 (17)	0.0787 (19)	0.148 (3)	0.0083 (14)	0.0311 (16)	0.0179 (18)
O1	0.105 (2)	0.0664 (17)	0.353 (6)	0.0126 (15)	0.091 (3)	0.017 (2)
O2	0.0574 (15)	0.127 (2)	0.252 (4)	0.0171 (15)	0.0225 (18)	−0.013 (2)
O3	0.0483 (9)	0.0532 (10)	0.0770 (12)	−0.0036 (7)	0.0049 (8)	−0.0015 (8)
O4	0.0619 (11)	0.0864 (14)	0.0648 (11)	−0.0253 (10)	0.0017 (8)	−0.0029 (9)
O5	0.0797 (13)	0.0928 (15)	0.0581 (11)	−0.0337 (11)	0.0008 (9)	0.0035 (10)

C1—O3	1.361 (3)	C7—C8	1.524 (3)
C1—C2	1.380 (4)	C7—C9	1.525 (4)
C1—C6	1.382 (3)	C8—O4	1.215 (3)
C2—C3	1.379 (4)	C8—O5	1.285 (3)
C2—H2	0.9300	C9—H9A	0.9600
C3—C4	1.374 (4)	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C4—C5	1.365 (4)	C10—H10A	0.9600
C4—N1	1.462 (4)	C10—H10B	0.9600
C5—C6	1.358 (4)	C10—H10C	0.9600
C5—H5	0.9300	N1—O2	1.193 (4)
C6—H6	0.9300	N1—O1	1.202 (4)
C7—O3	1.443 (3)	O5—H5A	0.92 (4)
C7—C10	1.513 (4)
O3—C1—C2	126.6 (2)	C10—C7—C9	111.2 (2)
O3—C1—C6	114.0 (2)	C8—C7—C9	107.5 (2)
C2—C1—C6	119.3 (2)	O4—C8—O5	124.3 (2)
C3—C2—C1	119.6 (2)	O4—C8—C7	121.3 (2)
C3—C2—H2	120.2	O5—C8—C7	114.4 (2)
C1—C2—H2	120.2	C7—C9—H9A	109.5
C4—C3—C2	119.3 (3)	C7—C9—H9B	109.5
C4—C3—H3	120.3	H9A—C9—H9B	109.5
C2—C3—H3	120.3	C7—C9—H9C	109.5
C5—C4—C3	121.5 (2)	H9A—C9—H9C	109.5
C5—C4—N1	118.6 (2)	H9B—C9—H9C	109.5
C3—C4—N1	119.9 (3)	C7—C10—H10A	109.5
C6—C5—C4	118.9 (2)	C7—C10—H10B	109.5
C6—C5—H5	120.5	H10A—C10—H10B	109.5
C4—C5—H5	120.5	C7—C10—H10C	109.5
C5—C6—C1	121.2 (2)	H10A—C10—H10C	109.5
C5—C6—H6	119.4	H10B—C10—H10C	109.5
C1—C6—H6	119.4	O2—N1—O1	122.1 (3)
O3—C7—C10	111.1 (2)	O2—N1—C4	119.0 (3)
O3—C7—C8	111.08 (19)	O1—N1—C4	118.6 (3)
C10—C7—C8	112.3 (2)	C1—O3—C7	122.60 (18)
O3—C7—C9	103.2 (2)	C8—O5—H5A	111 (2)
O3—C1—C2—C3	−177.1 (3)	O3—C7—C8—O5	42.7 (3)
C6—C1—C2—C3	−0.3 (4)	C10—C7—C8—O5	167.7 (2)
C1—C2—C3—C4	0.2 (5)	C9—C7—C8—O5	−69.6 (3)
C2—C3—C4—C5	0.2 (5)	C5—C4—N1—O2	2.2 (5)
C2—C3—C4—N1	−178.2 (3)	C3—C4—N1—O2	−179.4 (4)
C3—C4—C5—C6	−0.6 (4)	C5—C4—N1—O1	−172.6 (4)
N1—C4—C5—C6	177.8 (3)	C3—C4—N1—O1	5.9 (5)
C4—C5—C6—C1	0.5 (4)	C2—C1—O3—C7	−22.5 (4)
O3—C1—C6—C5	177.1 (2)	C6—C1—O3—C7	160.6 (2)
C2—C1—C6—C5	−0.1 (4)	C10—C7—O3—C1	−58.6 (3)
O3—C7—C8—O4	−139.5 (2)	C8—C7—O3—C1	67.2 (3)
C10—C7—C8—O4	−14.5 (3)	C9—C7—O3—C1	−177.9 (2)
C9—C7—C8—O4	108.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4i	0.92 (4)	1.75 (4)	2.659 (3)	173 (3)
C6—H6···O1ii	0.93	2.34	3.165 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O4i	0.92 (4)	1.75 (4)	2.659 (3)	173 (3)
C6—H6⋯O1ii	0.93	2.34	3.165 (4)	147

Symmetry codes: (i) ; (ii) .