organic compounds
of 2-benzenesulfonamido-3-hydroxypropanoic acid
aDepartment of Chemistry, Institute of Natural Sciences, University of Gujrat, Gujrat 50700, Pakistan, and bDepartment of Physics, University of Sargodha, Sargodha, Punjab, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
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.
Keywords: crystal structure; benzenesulfonamido; propanoic acid; sulfonyl group; O—H⋯O hydrogen bonds.
CCDC reference: 1433189
1. Related literature
For related structures, see: Aguilar-Castro et al. (2004); Arshad et al. (2009, 2012); Zolotarev et al. (2014).
2. Experimental
2.1. Crystal data
|
2.3. Refinement
Data collection: APEX2 (Bruker, 2007); cell 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).
Supporting information
CCDC reference: 1433189
https://doi.org/10.1107/S2056989015020149/hb7530sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015020149/hb7530Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015020149/hb7530Isup3.cml
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.
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 Uiso(H) = xUeq(C, N, O), where x = 1.5 for hydroxy and x = 1.2 for all other H-atoms.
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).
For related structures, see: Aguilar-Castro et al. (2004); Arshad et al. (2009, 2012); Zolotarev et al. (2014).
Data collection: APEX2 (Bruker, 2007); cell
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).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. |
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 |
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 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) |
C9H11NO5S | V = 1080.78 (15) Å3 |
Mr = 245.25 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.0464 (4) Å | µ = 0.31 mm−1 |
b = 9.9752 (8) Å | T = 296 K |
c = 21.4701 (17) Å | 0.40 × 0.20 × 0.18 mm |
Bruker Kappa APEXII CCD diffractometer | 2354 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1978 reflections with I > 2σ(I) |
Tmin = 0.890, Tmax = 0.950 | Rint = 0.025 |
5013 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | Δρmax = 0.21 e Å−3 |
S = 1.03 | Δρmin = −0.28 e Å−3 |
2354 reflections | Absolute structure: Flack x determined using 919 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
149 parameters | Absolute structure parameter: 0.05 (5) |
0 restraints |
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 | ||
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* |
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) |
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) |
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. |
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. |
Acknowledgements
The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Ex-Vice Chancellor, University of Sargodha, Pakistan.
References
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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).