[(2-Nitro­phen­yl)sulfin­yl]acetic acid

In the title compound, C₈H₇NO₅S, all bond lengths and angles are normal. Inter­molecular O—H...O hydrogen bonds link the mol­ecules into helical chains running along the b axis. The crystal packing is further stabilized by weak inter­molecular C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.086
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

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   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

[(2-Nitrophenyl)sulfinyl]acetic acid

Crystal data

C8H7NO5S	F(000) = 472
Mr = 229.21	Dx = 1.625 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7133 reflections
a = 13.809 (3) Å	θ = 6.0–54.9°
b = 7.7892 (16) Å	µ = 0.35 mm^−1
c = 8.7858 (18) Å	T = 291 K
β = 97.47 (3)°	Block, yellow
V = 937.0 (3) Å^3	0.18 × 0.16 × 0.14 mm
Z = 4

Data collection

Rigaku RAXIS-RAPID diffractometer	2133 independent reflections
Radiation source: fine-focus sealed tube	1770 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scan	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
Tmin = 0.941, Tmax = 0.953	k = −10→10
8862 measured reflections	l = −11→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) = 0.086	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0472P)^2 + 0.1946P] where P = (Fo^2 + 2Fc^2)/3
2133 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1	0.23430 (11)	0.90149 (18)	0.59864 (18)	0.0291 (3)
C2	0.15383 (11)	0.91009 (19)	0.48517 (19)	0.0333 (3)
C3	0.10334 (13)	0.7657 (2)	0.4290 (2)	0.0443 (4)
H1	0.0491	0.7755	0.3548	0.053*
C4	0.13440 (14)	0.6073 (2)	0.4843 (2)	0.0466 (5)
H2	0.1012	0.5088	0.4475	0.056*
C5	0.21501 (14)	0.5946 (2)	0.5947 (2)	0.0434 (4)
H3	0.2367	0.4871	0.6303	0.052*
C6	0.26374 (12)	0.7404 (2)	0.6528 (2)	0.0373 (4)
H4	0.3168	0.7301	0.7290	0.045*
C7	0.38771 (12)	1.1141 (2)	0.57172 (18)	0.0330 (3)
H5	0.4296	1.0137	0.5784	0.040*
H6	0.3584	1.1275	0.4659	0.040*
C8	0.44656 (12)	1.2715 (2)	0.62351 (17)	0.0321 (3)
N1	0.12157 (11)	1.07551 (19)	0.41904 (18)	0.0420 (4)
O1	0.04238 (12)	1.0836 (2)	0.3394 (2)	0.0728 (5)
O2	0.17602 (11)	1.19828 (17)	0.44542 (17)	0.0575 (4)
O3	0.34566 (8)	1.02085 (15)	0.84275 (12)	0.0360 (3)
O4	0.42182 (9)	1.37662 (15)	0.71128 (14)	0.0428 (3)
O5	0.52796 (8)	1.27756 (16)	0.55985 (15)	0.0431 (3)
H7	0.5606	1.3604	0.5935	0.065*
S1	0.29334 (3)	1.08769 (5)	0.69508 (4)	0.02868 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0283 (7)	0.0276 (7)	0.0312 (8)	0.0010 (6)	0.0037 (6)	−0.0014 (6)
C2	0.0303 (8)	0.0308 (8)	0.0378 (8)	0.0040 (6)	0.0012 (6)	−0.0022 (6)
C3	0.0368 (9)	0.0432 (9)	0.0503 (11)	−0.0016 (8)	−0.0039 (8)	−0.0107 (8)
C4	0.0444 (10)	0.0332 (9)	0.0623 (12)	−0.0073 (8)	0.0075 (9)	−0.0115 (8)
C5	0.0474 (10)	0.0261 (8)	0.0578 (11)	0.0028 (7)	0.0117 (8)	0.0003 (7)
C6	0.0366 (8)	0.0319 (8)	0.0425 (9)	0.0035 (7)	0.0024 (7)	0.0037 (7)
C7	0.0367 (8)	0.0327 (8)	0.0298 (8)	−0.0038 (7)	0.0053 (6)	−0.0021 (6)
C8	0.0349 (8)	0.0327 (8)	0.0273 (8)	−0.0036 (6)	−0.0016 (6)	0.0025 (6)
N1	0.0425 (8)	0.0385 (8)	0.0420 (8)	0.0083 (7)	−0.0056 (7)	0.0008 (6)
O1	0.0585 (10)	0.0653 (10)	0.0833 (11)	0.0142 (8)	−0.0334 (9)	0.0085 (8)
O2	0.0666 (9)	0.0342 (7)	0.0660 (9)	0.0000 (7)	−0.0128 (7)	0.0094 (6)
O3	0.0390 (6)	0.0412 (6)	0.0268 (6)	0.0026 (5)	0.0005 (5)	−0.0001 (5)
O4	0.0491 (7)	0.0389 (6)	0.0406 (7)	−0.0062 (5)	0.0073 (6)	−0.0099 (5)
O5	0.0365 (6)	0.0442 (7)	0.0491 (7)	−0.0103 (5)	0.0078 (5)	−0.0093 (6)
S1	0.0298 (2)	0.02680 (19)	0.0289 (2)	0.00161 (15)	0.00178 (14)	−0.00163 (14)

Geometric parameters (Å, º)

C1—C6	1.384 (2)	C6—H4	0.9300
C1—C2	1.395 (2)	C7—C8	1.508 (2)
C1—S1	1.8184 (15)	C7—S1	1.8117 (17)
C2—C3	1.380 (2)	C7—H5	0.9700
C2—N1	1.459 (2)	C7—H6	0.9700
C3—C4	1.374 (3)	C8—O4	1.2043 (19)
C3—H1	0.9300	C8—O5	1.320 (2)
C4—C5	1.381 (3)	N1—O2	1.220 (2)
C4—H2	0.9300	N1—O1	1.221 (2)
C5—C6	1.384 (2)	O3—S1	1.4941 (12)
C5—H3	0.9300	O5—H7	0.8200
C6—C1—C2	117.41 (14)	C1—C6—H4	119.7
C6—C1—S1	117.97 (12)	C8—C7—S1	108.24 (11)
C2—C1—S1	124.20 (11)	C8—C7—H5	110.0
C3—C2—C1	122.34 (15)	S1—C7—H5	110.0
C3—C2—N1	117.60 (15)	C8—C7—H6	110.0
C1—C2—N1	120.04 (13)	S1—C7—H6	110.0
C4—C3—C2	119.03 (16)	H5—C7—H6	108.4
C4—C3—H1	120.5	O4—C8—O5	125.10 (15)
C2—C3—H1	120.5	O4—C8—C7	124.02 (15)
C3—C4—C5	119.90 (16)	O5—C8—C7	110.89 (13)
C3—C4—H2	120.1	O2—N1—O1	123.54 (15)
C5—C4—H2	120.1	O2—N1—C2	117.90 (13)
C4—C5—C6	120.59 (16)	O1—N1—C2	118.55 (15)
C4—C5—H3	119.7	C8—O5—H7	109.5
C6—C5—H3	119.7	O3—S1—C7	104.76 (7)
C5—C6—C1	120.70 (15)	O3—S1—C1	105.28 (7)
C5—C6—H4	119.7	C7—S1—C1	97.21 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H7···O3^i	0.82	1.83	2.6422 (17)	168
C3—H1···O1^ii	0.93	2.49	3.223 (2)	136
C7—H6···O4^iii	0.97	2.51	3.262 (2)	135

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x, y−1/2, −z+1/2; (iii) x, −y+5/2, z−1/2.