Hydrogen-bonded molecular ladders in S-(4-nitrophenyl)thioglycolic acid

Molecules of the title compound, [(4-nitro­phenyl)­sulfanyl]­acetic acid, C₈H₇NO₄S, are linked by paired O-H...O hydrogen bonds [H...O 1.81 Å, O...O 2.6456 (15) Å and O-H...O 178°] into centrosymmetric dimers containing an R(8) motif. A single C-H...O hydrogen bond having a nitro O atom as acceptor [H...O 2.47 Å, 3.3018 (19) Å and C-H...O 147°] links the dimers into a molecular ladder, and neighbouring ladders are weakly linked into sheets by aromatic [pi]-[pi]-stacking interactions.

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

[(4-nitrophenyl)sulfanyl]acetic acid

Crystal data

C8H7NO4S	Z = 2
Mr = 213.21	F(000) = 220
Triclinic, P1	Dx = 1.649 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1540 (3) Å	Cell parameters from 1902 reflections
b = 7.8750 (2) Å	θ = 3.2–27.5°
c = 8.0352 (3) Å	µ = 0.36 mm^−1
α = 73.8820 (16)°	T = 150 K
β = 85.7214 (13)°	Block, yellow
γ = 80.9841 (15)°	0.4 × 0.2 × 0.1 mm
V = 429.29 (3) Å^3

Data collection

Nonius KappaCCD area-detector diffractometer	1902 independent reflections
Radiation source: fine-focus sealed X-ray tube	1701 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.869, Tmax = 0.965	k = −10→9
5562 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0409P)^2 + 0.1827P] where P = (Fo^2 + 2Fc^2)/3
1902 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High-redundancy data were used in the scaling program, hence the `multi-scan' code word was used.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.13044 (18)	1.73074 (17)	−0.28790 (16)	0.0179 (3)
O1	0.03559 (18)	1.76769 (16)	−0.41747 (15)	0.0299 (3)
O2	0.19580 (17)	1.84244 (15)	−0.23817 (15)	0.0262 (3)
C1	0.16934 (19)	1.54351 (19)	−0.18877 (18)	0.0142 (3)
C2	0.1146 (2)	1.4153 (2)	−0.25550 (18)	0.0170 (3)
C3	0.15042 (19)	1.23875 (19)	−0.16335 (18)	0.0154 (3)
C4	0.23779 (19)	1.19053 (19)	−0.00328 (18)	0.0138 (3)
C5	0.2920 (2)	1.3224 (2)	0.06133 (18)	0.0156 (3)
C6	0.25774 (19)	1.5002 (2)	−0.03215 (18)	0.0155 (3)
S1	0.26817 (5)	0.96108 (5)	0.09835 (4)	0.01653 (13)
C7	0.3844 (2)	0.9426 (2)	0.29483 (19)	0.0168 (3)
C8	0.4329 (2)	0.7472 (2)	0.38365 (18)	0.0161 (3)
O3	0.38774 (15)	0.62904 (14)	0.33039 (14)	0.0206 (3)
O4	0.52844 (16)	0.71778 (14)	0.52481 (13)	0.0210 (3)
H2	0.0533	1.4487	−0.3630	0.020*
H3	0.1158	1.1490	−0.2085	0.018*
H5	0.3522	1.2901	0.1693	0.019*
H6	0.2944	1.5907	0.0106	0.019*
H7A	0.5009	0.9997	0.2678	0.020*
H7B	0.2996	1.0026	0.3708	0.020*
H4	0.5523	0.6073	0.5702	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0212 (6)	0.0130 (6)	0.0174 (6)	−0.0001 (5)	0.0022 (5)	−0.0026 (5)
O1	0.0417 (7)	0.0181 (6)	0.0260 (6)	0.0001 (5)	−0.0149 (5)	0.0016 (5)
O2	0.0394 (7)	0.0116 (6)	0.0289 (6)	−0.0050 (5)	−0.0032 (5)	−0.0065 (5)
C1	0.0146 (7)	0.0100 (7)	0.0161 (7)	0.0004 (5)	0.0006 (5)	−0.0018 (5)
C2	0.0180 (7)	0.0176 (8)	0.0157 (7)	−0.0019 (6)	−0.0042 (5)	−0.0041 (6)
C3	0.0164 (7)	0.0125 (7)	0.0188 (7)	−0.0024 (5)	−0.0033 (5)	−0.0056 (6)
C4	0.0115 (6)	0.0114 (7)	0.0166 (7)	−0.0011 (5)	0.0007 (5)	−0.0012 (5)
C5	0.0165 (7)	0.0157 (8)	0.0152 (7)	−0.0012 (5)	−0.0033 (5)	−0.0050 (6)
C6	0.0148 (7)	0.0141 (7)	0.0184 (7)	−0.0026 (5)	0.0004 (5)	−0.0058 (6)
S1	0.0205 (2)	0.0100 (2)	0.0182 (2)	−0.00275 (14)	−0.00484 (14)	−0.00086 (14)
C7	0.0211 (7)	0.0121 (7)	0.0161 (7)	−0.0009 (5)	−0.0032 (5)	−0.0022 (5)
C8	0.0174 (7)	0.0149 (8)	0.0144 (7)	0.0000 (6)	0.0015 (5)	−0.0030 (6)
O3	0.0277 (6)	0.0121 (6)	0.0212 (6)	−0.0020 (4)	−0.0071 (4)	−0.0023 (4)
O4	0.0329 (6)	0.0124 (6)	0.0162 (5)	0.0009 (4)	−0.0079 (4)	−0.0020 (4)

Geometric parameters (Å, º)

N1—O2	1.2264 (17)	C5—C6	1.386 (2)
N1—O1	1.2265 (17)	C5—H5	0.9500
N1—C1	1.4623 (18)	C6—H6	0.9500
C1—C6	1.383 (2)	S1—C7	1.7987 (15)
C1—C2	1.384 (2)	C7—C8	1.502 (2)
C2—C3	1.376 (2)	C7—H7A	0.9900
C2—H2	0.9500	C7—H7B	0.9900
C3—C4	1.4013 (19)	C8—O3	1.2203 (18)
C3—H3	0.9500	C8—O4	1.3144 (17)
C4—C5	1.397 (2)	O4—H4	0.8400
S1—C4	1.7502 (14)
C6—C1—C2	122.23 (13)	C1—C6—H6	120.6
C6—C1—N1	119.43 (13)	C5—C6—H6	120.6
C2—C1—N1	118.33 (13)	C4—S1—C7	103.67 (7)
C3—C2—C1	118.84 (13)	C8—C7—S1	107.51 (10)
C3—C2—H2	120.6	C8—C7—H7A	110.2
C1—C2—H2	120.6	S1—C7—H7A	110.2
C2—C3—C4	120.35 (13)	C8—C7—H7B	110.2
C2—C3—H3	119.8	S1—C7—H7B	110.2
C4—C3—H3	119.8	H7A—C7—H7B	108.5
C5—C4—C3	119.75 (13)	O3—C8—O4	123.84 (13)
S1—C4—C3	114.32 (11)	O3—C8—C7	123.49 (13)
S1—C4—C5	125.93 (11)	O4—C8—C7	112.66 (12)
C6—C5—C4	119.99 (13)	C8—O4—H4	109.5
C6—C5—H5	120.0	O1—N1—O2	123.40 (13)
C4—C5—H5	120.0	O2—N1—C1	118.34 (12)
C1—C6—C5	118.83 (13)	O1—N1—C1	118.26 (12)
O1—N1—C1—C2	6.7 (2)	C3—C4—S1—C7	179.23 (11)
O1—N1—C1—C6	−172.92 (13)	C4—S1—C7—C8	−174.84 (10)
O2—N1—C1—C2	−172.65 (13)	S1—C7—C8—O3	−3.79 (18)
O2—N1—C1—C6	7.8 (2)	S1—C7—C8—O4	176.42 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3^i	0.84	1.81	2.6456 (15)	178
C3—H3···O2^ii	0.95	2.47	3.3018 (19)	147

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z.