Crystal structure of 2-benzene­sulfon­amido-3-hy­droxy­propanoic acid

Abstract

In the title compound, C₉H₁₁NO₅S, the O=S=O plane of the sulfonyl group is twisted at a dihedral angle of 52.54 (16)° with respect to the benzene ring. The dihedral angle between the carb­oxy­lic acid group and the benzene ring is 49.91 (16)°. In the crystal, C—H⋯O, N—H⋯O and O—H⋯O hydrogen bonds link the mol­ecules into (001) sheets.

Related literature  

For related structures, see: Aguilar-Castro et al. (2004 ▸); Arshad et al. (2009 ▸, 2012 ▸); Zolotarev et al. (2014 ▸).

Experimental  

Crystal data  

• C₉H₁₁NO₅S

• M _r = 245.25

• Orthorhombic,

• a = 5.0464 (4) Å

• b = 9.9752 (8) Å

• c = 21.4701 (17) Å

• V = 1080.78 (15) ų

• Z = 4

• Mo Kα radiation

• μ = 0.31 mm⁻¹

• T = 296 K

• 0.40 × 0.20 × 0.18 mm

Data collection  

• Bruker Kappa APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T _min = 0.890, T _max = 0.950

• 5013 measured reflections

• 2354 independent reflections

• 1978 reflections with I > 2σ(I)

• R _int = 0.025

Refinement  

• R[F ² > 2σ(F ²)] = 0.042

• wR(F ²) = 0.093

• S = 1.03

• 2354 reflections

• 149 parameters

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.21 e Å⁻³

• Δρ_min = −0.28 e Å⁻³

• Absolute structure: Flack x determined using 919 quotients [(I ⁺)−(I ⁻)]/[(I ⁺)⁺(I ⁻)] (Parsons et al., 2013 ▸)

• Absolute structure parameter: 0.05 (5)

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT (Bruker, 2007 ▸); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸).

Supplementary Material

CCDC reference: 1433189

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O1H1O3i	0.84(5)	1.81(5)	2.621(4)	164(5)
O3H3O5i	0.82	1.96	2.754(3)	164
N1H1AO4ii	0.86	2.39	3.066(4)	136
C2H2O2iii	0.98	2.48	3.425(5)	162
C6H6O5iv	0.93	2.52	3.342(5)	148
C7H7O2v	0.93	2.58	3.347(5)	141

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

supplementary crystallographic information

S1. Comment

The title compound (I), (Fig. 1) has been synthesized for complexation and other studius.

The crystal structures of N-((4-methylphenyl)sulfonyl)serine (Zolotarev et al., 2014), N(S)-(p-toluenesulfonyl)-L-alanine (Aguilar-Castro et al., 2004), 2-benzenesulfonamido-3-methylbutyric acid (Arshad et al., 2012) and (2R)-2-benzenesulfonamido-2- phenylethanoic acid (Arshad et al., 2009) have been reported which are related to the title compound.

The aminoacetic acid moiety B (C1/C2/N1/O1/O2) is roughly planar with r.m.s. deviation of 0.0588 Å. The dihedral angle between the benzene ring and B is 52.96 (14)°. The sulfonyl group C (S1/O4/O5) is oriented at a dihedral angle of 52.54 (16)° with the parent benzene ring. In the crystal, the molecules are linked into a two-dimensional polymeric network (Table 2, Fig. 2) due to H-bondings of C–H···O, N–H···O and O–H···O types with base vectors [100], [010] and in the plane (001).

S2. Experimental

The title compound was prepared by using equimolar ratio of L-serine and benzenesulfonyl chloride in 40 ml water. The benzenesulfonyl chloride disolved in distilled water was added pinch by pinch in the L-serine already disolved in distilled water and stirred at 296–298 K, while keeping the pH of the reaction mixture was maintained at 8–9 by adding 1.0 M sodium bicarbonate solution. The 1.0 M HCl solution was added after an hour which resulted in the form of white precipitates. The precipitates obtained were filtered and dried from which colourless needles of (I) were obtained after recrystallization from ethanol solution after 48 h. Yield: 68% Melting point: 493 K.

S3. Refinement

The coordinates of H-atom of carboxyl group were refined. The other H-atoms were positioned geometrically (O—H = 0.82, N—H = 0.86, C–H = 0.93—0.98 Å) and refined as riding with U_iso(H) = xU_eq(C, N, O), where x = 1.5 for hydroxy and x = 1.2 for all other H-atoms.

Figures

Fig. 1.

View of the asymmetric unit of title compound with displacement ellipsoids drawn at the 50% probability level.

Fig. 2.

The partial packing (PLATON; Spek, 2009), which shows that molecules form two dimensional polymeric network.

Crystal data

C9H11NO5S	Dx = 1.507 Mg m−3
Mr = 245.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1978 reflections
a = 5.0464 (4) Å	θ = 2.8–27.1°
b = 9.9752 (8) Å	µ = 0.31 mm−1
c = 21.4701 (17) Å	T = 296 K
V = 1080.78 (15) Å3	Needle, colorless
Z = 4	0.40 × 0.20 × 0.18 mm
F(000) = 512

Data collection

Bruker Kappa APEXII CCD diffractometer	2354 independent reflections
Radiation source: fine-focus sealed tube	1978 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 7.80 pixels mm-1	θmax = 27.1°, θmin = 2.8°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→12
Tmin = 0.890, Tmax = 0.950	l = −27→27
5013 measured reflections

Refinement

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) = 0.093	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.1053P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2354 reflections	Δρmax = 0.21 e Å−3
149 parameters	Δρmin = −0.28 e Å−3
0 restraints	Absolute structure: Flack x determined using 919 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (5)

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
S1	0.68841 (17)	0.37500 (8)	0.12794 (3)	0.0362 (2)
O1	0.7864 (6)	0.8154 (3)	0.20233 (14)	0.0624 (8)
H1	0.871 (11)	0.885 (5)	0.194 (2)	0.094*
O2	1.1199 (6)	0.6949 (3)	0.16402 (14)	0.0651 (8)
O3	0.9705 (7)	0.5474 (2)	0.30216 (11)	0.0583 (8)
H3	1.0059	0.6065	0.3274	0.087*
O4	0.4135 (5)	0.3816 (3)	0.14371 (11)	0.0504 (6)
O5	0.8178 (6)	0.2474 (2)	0.12476 (11)	0.0502 (6)
N1	0.8462 (6)	0.4600 (2)	0.17945 (11)	0.0368 (6)
H1A	0.9985	0.4323	0.1920	0.044*
C1	0.9047 (8)	0.7029 (3)	0.18768 (14)	0.0406 (8)
C2	0.7369 (7)	0.5833 (3)	0.20543 (14)	0.0384 (8)
H2	0.5583	0.5962	0.1886	0.046*
C3	0.7171 (9)	0.5712 (4)	0.27649 (16)	0.0530 (10)
H3A	0.6444	0.6533	0.2936	0.064*
H3B	0.5990	0.4981	0.2873	0.064*
C4	0.7318 (7)	0.4526 (3)	0.05482 (14)	0.0365 (8)
C5	0.9275 (9)	0.4077 (4)	0.01556 (16)	0.0542 (10)
H5	1.0338	0.3355	0.0269	0.065*
C6	0.9645 (11)	0.4717 (4)	−0.04132 (17)	0.0653 (12)
H6	1.0988	0.4436	−0.0679	0.078*
C7	0.8028 (10)	0.5765 (4)	−0.05829 (16)	0.0609 (11)
H7	0.8250	0.6180	−0.0967	0.073*
C8	0.6103 (9)	0.6193 (4)	−0.01864 (17)	0.0618 (12)
H8	0.5028	0.6909	−0.0301	0.074*
C9	0.5718 (9)	0.5581 (4)	0.03840 (17)	0.0512 (9)
H9	0.4395	0.5879	0.0652	0.061*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
S1	0.0337 (4)	0.0291 (3)	0.0459 (4)	−0.0024 (4)	−0.0051 (4)	0.0017 (3)
O1	0.061 (2)	0.0327 (13)	0.0933 (19)	0.0046 (14)	0.0105 (17)	−0.0028 (13)
O2	0.054 (2)	0.0441 (14)	0.097 (2)	0.0024 (14)	0.0283 (17)	0.0134 (14)
O3	0.089 (2)	0.0342 (13)	0.0514 (14)	0.0014 (15)	−0.0182 (15)	−0.0063 (10)
O4	0.0350 (13)	0.0529 (14)	0.0634 (14)	−0.0087 (13)	−0.0019 (13)	0.0046 (12)
O5	0.0590 (17)	0.0282 (11)	0.0635 (14)	0.0039 (11)	−0.0118 (16)	0.0015 (10)
N1	0.0325 (16)	0.0352 (14)	0.0428 (12)	0.0059 (13)	−0.0089 (14)	−0.0030 (11)
C1	0.042 (2)	0.0349 (17)	0.0444 (17)	0.0068 (17)	−0.0013 (18)	0.0026 (14)
C2	0.0300 (19)	0.0357 (16)	0.0496 (16)	0.0040 (14)	−0.0014 (16)	−0.0043 (13)
C3	0.059 (3)	0.0427 (19)	0.0569 (19)	−0.005 (2)	0.025 (2)	−0.0085 (15)
C4	0.036 (2)	0.0331 (15)	0.0405 (14)	−0.0015 (16)	−0.0064 (16)	−0.0051 (12)
C5	0.059 (3)	0.051 (2)	0.0528 (19)	0.018 (2)	0.001 (2)	−0.0045 (16)
C6	0.081 (3)	0.069 (3)	0.0457 (19)	0.011 (3)	0.014 (2)	−0.011 (2)
C7	0.080 (3)	0.062 (2)	0.0400 (16)	0.000 (3)	−0.006 (2)	0.0020 (16)
C8	0.071 (3)	0.057 (2)	0.058 (2)	0.014 (2)	−0.011 (2)	0.0106 (19)
C9	0.048 (2)	0.050 (2)	0.0560 (19)	0.0159 (19)	0.003 (2)	0.0046 (17)

Geometric parameters (Å, º)

S1—O4	1.429 (3)	C3—H3A	0.9700
S1—O5	1.432 (2)	C3—H3B	0.9700
S1—N1	1.605 (3)	C4—C9	1.373 (5)
S1—C4	1.764 (3)	C4—C5	1.374 (5)
O1—C1	1.310 (4)	C5—C6	1.391 (5)
O1—H1	0.84 (5)	C5—H5	0.9300
O2—C1	1.201 (4)	C6—C7	1.375 (6)
O3—C3	1.413 (5)	C6—H6	0.9300
O3—H3	0.8200	C7—C8	1.360 (6)
N1—C2	1.458 (4)	C7—H7	0.9300
N1—H1A	0.8600	C8—C9	1.382 (5)
C1—C2	1.512 (5)	C8—H8	0.9300
C2—C3	1.534 (5)	C9—H9	0.9300
C2—H2	0.9800
O4—S1—O5	119.67 (16)	C2—C3—H3A	109.7
O4—S1—N1	107.09 (15)	O3—C3—H3B	109.7
O5—S1—N1	106.03 (14)	C2—C3—H3B	109.7
O4—S1—C4	108.12 (15)	H3A—C3—H3B	108.2
O5—S1—C4	106.92 (15)	C9—C4—C5	121.0 (3)
N1—S1—C4	108.64 (14)	C9—C4—S1	119.5 (3)
C1—O1—H1	115 (4)	C5—C4—S1	119.5 (3)
C3—O3—H3	109.5	C4—C5—C6	119.1 (4)
C2—N1—S1	121.4 (2)	C4—C5—H5	120.5
C2—N1—H1A	119.3	C6—C5—H5	120.5
S1—N1—H1A	119.3	C7—C6—C5	120.1 (4)
O2—C1—O1	124.8 (4)	C7—C6—H6	119.9
O2—C1—C2	124.1 (3)	C5—C6—H6	119.9
O1—C1—C2	111.1 (3)	C8—C7—C6	119.7 (4)
N1—C2—C1	110.9 (3)	C8—C7—H7	120.1
N1—C2—C3	109.8 (3)	C6—C7—H7	120.1
C1—C2—C3	110.4 (3)	C7—C8—C9	121.1 (4)
N1—C2—H2	108.5	C7—C8—H8	119.4
C1—C2—H2	108.5	C9—C8—H8	119.4
C3—C2—H2	108.5	C4—C9—C8	118.9 (4)
O3—C3—C2	110.0 (3)	C4—C9—H9	120.6
O3—C3—H3A	109.7	C8—C9—H9	120.6
O4—S1—N1—C2	−37.2 (3)	N1—S1—C4—C9	−83.5 (3)
O5—S1—N1—C2	−166.0 (2)	O4—S1—C4—C5	−148.5 (3)
C4—S1—N1—C2	79.4 (3)	O5—S1—C4—C5	−18.4 (3)
S1—N1—C2—C1	−114.8 (3)	N1—S1—C4—C5	95.6 (3)
S1—N1—C2—C3	122.8 (3)	C9—C4—C5—C6	0.7 (6)
O2—C1—C2—N1	−11.0 (5)	S1—C4—C5—C6	−178.4 (3)
O1—C1—C2—N1	170.0 (3)	C4—C5—C6—C7	−1.4 (6)
O2—C1—C2—C3	111.1 (4)	C5—C6—C7—C8	1.4 (7)
O1—C1—C2—C3	−68.0 (4)	C6—C7—C8—C9	−0.8 (7)
N1—C2—C3—O3	59.3 (4)	C5—C4—C9—C8	−0.1 (6)
C1—C2—C3—O3	−63.3 (4)	S1—C4—C9—C8	179.1 (3)
O4—S1—C4—C9	32.4 (3)	C7—C8—C9—C4	0.1 (7)
O5—S1—C4—C9	162.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.84 (5)	1.81 (5)	2.621 (4)	164 (5)
O3—H3···O5i	0.82	1.96	2.754 (3)	164
N1—H1A···O4ii	0.86	2.39	3.066 (4)	136
C2—H2···O2iii	0.98	2.48	3.425 (5)	162
C6—H6···O5iv	0.93	2.52	3.342 (5)	148
C7—H7···O2v	0.93	2.58	3.347 (5)	141

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