Crystal structure of (2S)-3-methyl-2-[(naphthalen-1-ylsulfon­yl)amino]­butanoic acid

Muhammad Danish; Muhammad Nawaz Tahir; Nabila Jabeen; Muhammad Asam Raza

doi:10.1107/S2056989015007057

. 2015 Apr 15;71(Pt 5):o308. doi: 10.1107/S2056989015007057

Crystal structure of (2S)-3-methyl-2-[(naphthalen-1-ylsulfonyl)amino]butanoic acid

Muhammad Danish ^a, Muhammad Nawaz Tahir ^b,^*, Nabila Jabeen ^a, Muhammad Asam Raza ^a

PMCID: PMC4420138 PMID: 25995919

Abstract

The title compound, C₁₅H₁₇NO₄S, was synthesized from l-valine and naphthalene-1-sulfonyl chloride. The hydrogen-bonded carboxylic acid groups form a catemer C(4) motif extending along [100]. The catemer structure is reinforced by a rather long N—H⋯O hydrogen bond, between the sulfamide N—H group and a carboxylic acid O atom [H⋯O = 2.52 (2) Å], and a C—H⋯O hydrogen bond.

Keywords: crystal structure, catemer, naphthalen-1-ylsulfonyl, l-valine, hydrogen bonding, π–π stacking interactions

Related literature

For related structures, see: Aguilar-Castro et al. (2004 ▸); Arshad et al. (2012 ▸); Mubashar-ur-Rehman et al. (2013 ▸). graphic file with name e-71-0o308-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₇NO₄S
M _r = 307.35
Orthorhombic,
a = 5.5006 (3) Å
b = 13.7638 (8) Å
c = 20.2148 (14) Å
V = 1530.45 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.38 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T _min = 0.920, T _max = 0.956
7706 measured reflections
3290 independent reflections
2692 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.095
S = 1.02
3290 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 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; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015007057/gk2628sup1.cif

e-71-0o308-sup1.cif^{(24.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007057/gk2628Isup2.hkl

e-71-0o308-Isup2.hkl^{(180.7KB, hkl)}

Click here for additional data file.^{(5.6KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015007057/gk2628Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015007057/gk2628fig1.tif

View of the asymmetric unit of title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown as small circles of arbitrary radii.

Click here for additional data file.^{(1.8MB, tif)}

PLATON . DOI: 10.1107/S2056989015007057/gk2628fig2.tif

The partial packing (PLATON; Spek, 2009) which shows that molecules form one dimensional polymeric network with different hydrogen-bond ring motifs. H atoms not involved in hydrogen bonding are omitted for clarity.

CCDC reference: 1058549

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O1H1O2ⁱ	0.85(4)	1.86(4)	2.701(3)	173(4)
N1H1AO1ⁱⁱ	0.83(2)	2.52(2)	3.323(3)	166(3)
C2H2O3ⁱⁱⁱ	0.98	2.38	3.348(4)	169

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

S1. Comment

The title compound (Fig. 1) was synthesized for complexation and other studies.

The crystal structures of N-(p-toluenesulfonyl)-L-valine (Aguilar-Castro et al., 2004) and 2-benzenesulfonamido-3-methylbutyric acid (Arshad et al., 2012) have been reported which contain the L-valine as common moiety as in (I). The crystal structure of 2- (naphthalene-1-sulfonamido)-3-phenylpropanoic acid (Mubashar-ur-Rehman et al., 2013) has also been published which contains the naphthalene-1-sulfonamide group.

In (I), the aminoacetato moiety A (O1/O2/C1/C2/N1) of L-valine and naphthalene ring B (C6–C15) are planar with r.m.s. deviation of 0.0468 and 0.0163 Å, respectively. The dihedral angle between A/B is 69.26 (9)°. The sulfonyl group C (S1/O3/O4) is oriented at a dihedtal angle of 59.9 (1)° with the parent naphthalene ring. The H-atoms of carboxyl, amido and of substituted aminoacetato moiety are involved in H-bondings (Table 1, Fig. 2). There exist two types of ring motifs R₂²(8) and R₃³(11). The R₂²(8) ring is formed due to C—H···O and N—H···O interactions. The R₃³(11) ring is created due to O—H···O and N—H···O interactions in which three carboxyl groups are involved. The R₃³(11) rings are connected successively along the a- axis, whereas, the R₂²(8) rings are connected to R₃³(11) rings alternatively, from opposite ends (Fig. 2).

S2. Experimental

L-Valine (0.117 g, 1 mmol) and naphthalene-1-sulfonyl chloride (0.226 g, 1 mmol) were added to 30 ml of water. The reaction mixture was stirred at 323–328 K and pH of the reaction mixture was maintained at 8–9 by adding 1.0 M sodium bicarbonate solution. The heating was stopped when clear solution was obtained. After one hour 8 ml of 1.0 M HCl solution was added and white precipitate was formed. The precipitate was filtered and dried (yield: 70%; m.p. 421 K). White needles of the title compound were obtained after recrystallization from ethanol.