2-Methyl-2-(4-nitro-phenyl-sulfanyl)-propanoic acid.

The title compound, C(10)H(11)NO(4)S, is of inter-est with respect to its biological activity. The mol-ecules are linked into centrosymmetric dimers by inter-molecular O-H⋯O hydrogen bonds and the dimers are further connected into chains by weak C-H⋯O inter-actions.

Related literature

For related literature on fibrate structures and biological activity, see: 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 related literature, see: Bernstein et al. (1995 ▶); Desiraju (2002 ▶).

Experimental

Crystal data

C10H11NO4S

M = 241.26

Triclinic,

a = 6.9382 (8) Å

b = 9.4500 (11) Å

c = 9.6395 (11) Å

α = 66.371 (2)°

β = 87.995 (2)°

γ = 88.298 (2)°

V = 578.60 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 273 (2) K

0.32 × 0.23 × 0.18 mm

Data collection

Bruker SMART CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.92, T max = 0.95

5660 measured reflections

2036 independent reflections

1718 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.123

S = 1.08

2036 reflections

148 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus NT (Bruker, 2000 ▶); data reduction: SAINT-Plus NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL-NT (Bruker, 2000 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶) and publCIF (Westrip, 2007 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062678/ln2010sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062678/ln2010Isup2.hkl

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

C10H11NO4S	Z = 2
Mr = 241.26	F000 = 252
Triclinic, P1	Dx = 1.385 Mg m−3
Hall symbol: -P 1	Melting point: 394.9 K
a = 6.9382 (8) Å	Mo Kα radiation λ = 0.71073 Å
b = 9.4500 (11) Å	Cell parameters from 2036 reflections
c = 9.6395 (11) Å	θ = 2.3–25º
α = 66.371 (2)º	µ = 0.28 mm−1
β = 87.995 (2)º	T = 273 (2) K
γ = 88.298 (2)º	Plate, colourless
V = 578.60 (12) Å3	0.32 × 0.23 × 0.18 mm

Bruker CCD area detector diffractometer	2036 independent reflections
Radiation source: fine-focus sealed tube	1718 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 273(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	h = −8→8
Tmin = 0.92, Tmax = 0.95	k = −11→11
5660 measured reflections	l = −11→11

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.06P)2 + 0.156P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2036 reflections	Δρmax = 0.28 e Å−3
148 parameters	Δρmin = −0.17 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	0.1054 (3)	0.1894 (3)	0.6403 (2)	0.0531 (5)
C2	0.1738 (3)	0.0380 (3)	0.6935 (3)	0.0580 (6)
H2	0.3037	0.0168	0.7153	0.070*
C3	0.0525 (3)	−0.0797 (3)	0.7141 (3)	0.0576 (6)
H3	0.0982	−0.1813	0.7509	0.069*
C4	−0.1375 (3)	−0.0462 (3)	0.6797 (2)	0.0524 (5)
C5	−0.2096 (4)	0.1026 (3)	0.6234 (3)	0.0608 (6)
H5	−0.3388	0.1231	0.5988	0.073*
C6	−0.0871 (3)	0.2196 (3)	0.6045 (3)	0.0599 (6)
H6	−0.1336	0.3210	0.5669	0.072*
C7	0.2702 (4)	0.3441 (3)	0.8037 (3)	0.0624 (6)
C8	0.3733 (3)	0.1963 (3)	0.9005 (3)	0.0568 (6)
C9	0.0695 (4)	0.3533 (4)	0.8653 (3)	0.0837 (9)
H9A	0.0023	0.2602	0.8821	0.125*
H9B	0.0011	0.4402	0.7936	0.125*
H9C	0.0773	0.3653	0.9592	0.125*
C10	0.3903 (5)	0.4859 (3)	0.7791 (4)	0.0940 (10)
H10A	0.4076	0.4928	0.8745	0.141*
H10B	0.3247	0.5773	0.7119	0.141*
H10C	0.5140	0.4764	0.7354	0.141*
N1	−0.2678 (3)	−0.1730 (3)	0.7030 (2)	0.0674 (6)
O1	−0.2015 (3)	−0.3028 (2)	0.7498 (3)	0.0997 (7)
O2	−0.4350 (3)	−0.1430 (3)	0.6715 (3)	0.1118 (9)
O3	0.2868 (2)	0.0840 (2)	0.98479 (19)	0.0724 (5)
O4	0.5595 (3)	0.1977 (2)	0.8833 (2)	0.0839 (6)
H4	0.6034	0.1101	0.9283	0.126*
S1	0.26504 (9)	0.34147 (7)	0.61287 (7)	0.0636 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0654 (14)	0.0463 (12)	0.0439 (11)	0.0029 (10)	−0.0021 (10)	−0.0142 (9)
C2	0.0524 (13)	0.0544 (14)	0.0660 (14)	0.0081 (11)	−0.0043 (11)	−0.0233 (11)
C3	0.0646 (15)	0.0425 (12)	0.0637 (14)	0.0088 (10)	0.0004 (11)	−0.0201 (10)
C4	0.0580 (13)	0.0509 (12)	0.0505 (12)	0.0010 (10)	0.0029 (10)	−0.0230 (10)
C5	0.0566 (13)	0.0572 (14)	0.0687 (15)	0.0103 (11)	−0.0110 (11)	−0.0252 (12)
C6	0.0675 (15)	0.0447 (12)	0.0632 (14)	0.0124 (11)	−0.0135 (11)	−0.0170 (11)
C7	0.0765 (16)	0.0474 (13)	0.0621 (14)	0.0032 (11)	−0.0115 (12)	−0.0203 (11)
C8	0.0599 (15)	0.0550 (14)	0.0535 (13)	−0.0011 (11)	−0.0059 (11)	−0.0192 (11)
C9	0.090 (2)	0.084 (2)	0.0815 (19)	0.0282 (16)	−0.0080 (15)	−0.0396 (16)
C10	0.126 (3)	0.0560 (16)	0.102 (2)	−0.0089 (16)	−0.0276 (19)	−0.0311 (16)
N1	0.0681 (14)	0.0593 (13)	0.0789 (14)	−0.0041 (11)	0.0051 (11)	−0.0323 (11)
O1	0.0975 (15)	0.0514 (12)	0.144 (2)	−0.0033 (10)	−0.0158 (13)	−0.0309 (12)
O2	0.0606 (13)	0.0851 (15)	0.197 (3)	−0.0033 (11)	−0.0088 (14)	−0.0639 (16)
O3	0.0667 (11)	0.0628 (11)	0.0653 (11)	−0.0002 (9)	0.0036 (8)	−0.0026 (9)
O4	0.0596 (11)	0.0673 (12)	0.0976 (15)	−0.0026 (9)	−0.0058 (9)	−0.0041 (10)
S1	0.0762 (5)	0.0503 (4)	0.0543 (4)	−0.0081 (3)	−0.0034 (3)	−0.0100 (3)

C1—C6	1.384 (3)	C7—C10	1.531 (4)
C1—C2	1.387 (3)	C7—S1	1.851 (2)
C1—S1	1.769 (2)	C8—O3	1.208 (3)
C2—C3	1.361 (3)	C8—O4	1.296 (3)
C2—H2	0.9300	C9—H9A	0.9600
C3—C4	1.368 (3)	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C4—C5	1.374 (3)	C10—H10A	0.9600
C4—N1	1.462 (3)	C10—H10B	0.9600
C5—C6	1.364 (3)	C10—H10C	0.9600
C5—H5	0.9300	N1—O2	1.206 (3)
C6—H6	0.9300	N1—O1	1.207 (3)
C7—C8	1.508 (3)	O4—H4	0.8200
C7—C9	1.508 (4)
C6—C1—C2	119.0 (2)	C9—C7—S1	111.51 (18)
C6—C1—S1	120.86 (17)	C10—C7—S1	103.62 (19)
C2—C1—S1	120.08 (18)	O3—C8—O4	122.9 (2)
C3—C2—C1	120.5 (2)	O3—C8—C7	121.8 (2)
C3—C2—H2	119.7	O4—C8—C7	115.3 (2)
C1—C2—H2	119.7	C7—C9—H9A	109.5
C2—C3—C4	119.0 (2)	C7—C9—H9B	109.5
C2—C3—H3	120.5	H9A—C9—H9B	109.5
C4—C3—H3	120.5	C7—C9—H9C	109.5
C3—C4—C5	122.1 (2)	H9A—C9—H9C	109.5
C3—C4—N1	118.9 (2)	H9B—C9—H9C	109.5
C5—C4—N1	119.0 (2)	C7—C10—H10A	109.5
C6—C5—C4	118.4 (2)	C7—C10—H10B	109.5
C6—C5—H5	120.8	H10A—C10—H10B	109.5
C4—C5—H5	120.8	C7—C10—H10C	109.5
C5—C6—C1	120.9 (2)	H10A—C10—H10C	109.5
C5—C6—H6	119.6	H10B—C10—H10C	109.5
C1—C6—H6	119.6	O2—N1—O1	123.1 (2)
C8—C7—C9	111.5 (2)	O2—N1—C4	118.7 (2)
C8—C7—C10	111.5 (2)	O1—N1—C4	118.2 (2)
C9—C7—C10	112.9 (2)	C8—O4—H4	109.5
C8—C7—S1	105.22 (16)	C1—S1—C7	102.66 (11)
C6—C1—C2—C3	−1.8 (3)	C9—C7—C8—O4	−160.9 (2)
S1—C1—C2—C3	−179.55 (18)	C10—C7—C8—O4	−33.6 (3)
C1—C2—C3—C4	0.8 (4)	S1—C7—C8—O4	78.0 (2)
C2—C3—C4—C5	0.8 (4)	C3—C4—N1—O2	−179.4 (2)
C2—C3—C4—N1	−179.5 (2)	C5—C4—N1—O2	0.3 (4)
C3—C4—C5—C6	−1.3 (4)	C3—C4—N1—O1	−1.1 (3)
N1—C4—C5—C6	179.0 (2)	C5—C4—N1—O1	178.6 (2)
C4—C5—C6—C1	0.3 (4)	C6—C1—S1—C7	97.2 (2)
C2—C1—C6—C5	1.2 (4)	C2—C1—S1—C7	−85.1 (2)
S1—C1—C6—C5	178.97 (19)	C8—C7—S1—C1	68.65 (18)
C9—C7—C8—O3	20.9 (3)	C9—C7—S1—C1	−52.4 (2)
C10—C7—C8—O3	148.1 (3)	C10—C7—S1—C1	−174.16 (18)
S1—C7—C8—O3	−100.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3i	0.82	1.84	2.656 (3)	175
C2—H2···O2ii	0.93	2.46	3.211 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3i	0.82	1.84	2.656 (3)	175
C2—H2⋯O2ii	0.93	2.46	3.211 (3)	138

Symmetry codes: (i) ; (ii) .