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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Jul 28;68(Pt 8):o2573. doi: 10.1107/S1600536812033260

4-Methyl-2-(2-nitro­benzene­sulfon­amido)­penta­noic acid

Muhammad Nadeem Arshad a, Muhammad Danish b,*, Muhammad Nawaz Tahir c, Savera Khalid b, Abdullah M Asiri d,a
PMCID: PMC3415013  PMID: 22905000

Abstract

In the title compound, C12H16N2O6S, the S atom adopts a distorted tetra­hedral geometry with an O—S—O angle of 119.76 (13)°. The nitro group is twisted by 35.34 (2)° with respect to the aromatic ring; it accepts an N—H⋯O hydrogen bond, resulting in a S(7) motif. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds connect the mol­ecules into an infinite chain along the a axis. The methyl C atoms of the isopropyl group are disordered in a 1:1 ratio.

Related literature  

For a related structure, see: Arshad et al. (2010 ▶), For graph-set notation, see: Bernstein et al. (1995 ▶).graphic file with name e-68-o2573-scheme1.jpg

Experimental  

Crystal data  

  • C12H16N2O6S

  • M r = 316.33

  • Orthorhombic, Inline graphic

  • a = 6.9593 (5) Å

  • b = 10.7560 (8) Å

  • c = 20.8431 (14) Å

  • V = 1560.19 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.23 mm−1

  • T = 296 K

  • 0.45 × 0.38 × 0.29 mm

Data collection  

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.902, T max = 0.935

  • 11203 measured reflections

  • 2730 independent reflections

  • 2029 reflections with I > 2σ(I)

  • R int = 0.045

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.043

  • wR(F 2) = 0.090

  • S = 0.99

  • 2730 reflections

  • 212 parameters

  • 10 restraints

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

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.20 e Å−3

  • Absolute structure: Flack (1983 ▶), 1117 Friedel pairs

  • Flack parameter: 0.07 (10)

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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033260/ng5283sup1.cif

e-68-o2573-sup1.cif (25.6KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033260/ng5283Isup3.hkl

e-68-o2573-Isup3.hkl (134.1KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812033260/ng5283Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2N⋯O2 0.85 (1) 2.34 (4) 2.937 (3) 128 (4)
O6—H6O⋯O5i 0.85 (1) 1.87 (2) 2.702 (3) 166 (5)
N2—H2N⋯O5ii 0.85 (1) 2.38 (2) 3.169 (3) 155 (4)
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic.

Acknowledgments

The authors acknowledge the University of Sargodha for providing diffraction facilities at its Department of Physics.

supplementary crystallographic information

Comment

In order to explore the structural behaviour of sulfonamide derived from amino acids (Arshad et al., 2010), here we report the crystal structure of title compound.

The nitro group attached to aromatic ring is twisted at dihedral angle of 35.34 (2)°, with the maximum deviation from the two oxygen atoms being -0.532 (6) Å for O1 and 0.703 (5) Å for O2. An intramolecular N—H···O leads to the formation of a seven membered ring motif, S11(7) (Bernstein et al., 1995). The nitro group is oriented at an angle of 29.84 (6)° with respect to aromatic ring. Adjacent molecules are linked to form an infinite chain along a axis through O—H···O and N—H···O interactions (Table. 1, Fig. 2).

Experimental

L-lucine (0.20 g, 0.089 mmole) dissolved in 5–10 mL distilled water was treated with sodium carbonate (1M) to a pH of 8–9. 2-Nitrobenzenesulphonyl chloride (0.117 g, 0.089 mmole) added within 3–5 min. The pH was adjusted by sodium carbonate (1M). Then, dilute HCl was added dropwise to result in a pH 2–3. The precipitate was filtered, washed with plenty of water and dried. Suitable crystals was obtained upon recrystalization in methanol.

Refinement

All the C—H and H-atoms were positioned with idealized geometry with C—H = 0.93 Å for aromatic, C—H = 0.96 Å for methyl group and C—H = 0.97 Å for methylene, and were refined using a riding model with Uiso(H) = 1.2 Ueq(C) for aromatic and methylene and Uiso(H) = 1.5 Ueq(C) for methyl carbon atoms.

The N—H = 0.85 (1) and O—H = 0.85 (1) Å hydrogen atoms were located with difference map and were refined with Uiso(H) = 1.2 Ueq(N) and Uiso(H) = 1.5 Ueq(O).

Reaction does not affect the chirality of product, and the chirality is that of the reactant (L-Lucine).

The atoms C7—C11 were disordered over two positions with the occupancies of 0.50 for C7A—C11A and 0.50 for C7B—C11B. , The temperature factors of pairs of atoms were restrained to be identical. The C7a/C7b pair of atoms had the same site.

Figures

Fig. 1.

Fig. 1.

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The labelled molecular structure of (I) with 50% displacement ellipsoids.

Fig. 2.

Fig. 2.

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Unit cell packing showing hydrogen bonds, drawn using dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

Crystal data

C12H16N2O6S F(000) = 664
Mr = 316.33 Dx = 1.347 Mg m−3
Orthorhombic, P212121 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab Cell parameters from 1789 reflections
a = 6.9593 (5) Å θ = 2.7–19.5°
b = 10.7560 (8) Å µ = 0.23 mm−1
c = 20.8431 (14) Å T = 296 K
V = 1560.19 (19) Å3 Prismatic, colorless
Z = 4 0.45 × 0.38 × 0.29 mm
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Data collection

Bruker Kappa APEXII CCD diffractometer 2730 independent reflections
Radiation source: fine-focus sealed tube 2029 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.045
φ and ω scans θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007) h = −8→8
Tmin = 0.902, Tmax = 0.935 k = −12→12
11203 measured reflections l = −24→24
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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)] = 0.043 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.041P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99 (Δ/σ)max = 0.001
2730 reflections Δρmax = 0.15 e Å−3
212 parameters Δρmin = −0.20 e Å−3
10 restraints Absolute structure: Flack (1983), 1117 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: 0.07 (10)
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Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
S1 0.85210 (10) 0.49317 (7) 0.11950 (3) 0.0477 (2)
O1 0.6834 (3) 0.8270 (3) 0.21732 (13) 0.0947 (9)
N1 0.7618 (4) 0.7669 (3) 0.17531 (14) 0.0577 (7)
C1 1.0039 (4) 0.5944 (3) 0.16432 (12) 0.0445 (7)
O2 0.6943 (3) 0.7525 (2) 0.12226 (12) 0.0783 (7)
N2 0.8391 (4) 0.5420 (2) 0.04664 (11) 0.0433 (6)
C2 0.9481 (4) 0.7099 (3) 0.18997 (13) 0.0460 (8)
O3 0.6652 (3) 0.5002 (2) 0.14685 (10) 0.0691 (6)
C3 1.0679 (5) 0.7759 (3) 0.22962 (15) 0.0663 (10)
H3 1.0269 0.8509 0.2471 0.080*
O4 0.9507 (3) 0.37724 (17) 0.11794 (10) 0.0633 (6)
C4 1.2476 (5) 0.7316 (4) 0.24342 (17) 0.0794 (12)
H4 1.3294 0.7770 0.2698 0.095*
O5 1.1024 (3) 0.73707 (19) 0.01558 (9) 0.0505 (6)
C5 1.3060 (5) 0.6211 (4) 0.21847 (17) 0.0757 (11)
H5 1.4283 0.5913 0.2278 0.091*
O6 1.3184 (3) 0.5923 (2) −0.00802 (12) 0.0610 (6)
C6 1.1854 (5) 0.5525 (3) 0.17923 (14) 0.0569 (9)
H6 1.2276 0.4769 0.1627 0.068*
C12 1.1431 (4) 0.6294 (3) 0.00506 (12) 0.0429 (7)
C7A 1.0001 (4) 0.5234 (2) 0.00245 (13) 0.0401 (7) 0.50
H7A 1.0676 0.4480 0.0161 0.048* 0.50
C8A 0.938 (3) 0.504 (2) −0.0676 (7) 0.046 (3) 0.50
H81 0.8773 0.5793 −0.0830 0.056* 0.50
H82 1.0510 0.4890 −0.0936 0.056* 0.50
C9A 0.798 (5) 0.395 (3) −0.0769 (14) 0.0651 (12) 0.50
H9A 0.7104 0.3945 −0.0400 0.078* 0.50
C10A 0.676 (4) 0.413 (4) −0.1372 (12) 0.104 (7) 0.50
H10A 0.5886 0.4815 −0.1308 0.156* 0.50
H10B 0.6040 0.3390 −0.1457 0.156* 0.50
H10C 0.7580 0.4312 −0.1730 0.156* 0.50
C11A 0.903 (9) 0.272 (3) −0.077 (3) 0.116 (7) 0.50
H11A 0.9924 0.2710 −0.1126 0.174* 0.50
H11B 0.8124 0.2058 −0.0824 0.174* 0.50
H11C 0.9716 0.2622 −0.0378 0.174* 0.50
C7B 1.0001 (4) 0.5234 (2) 0.00245 (13) 0.0401 (7) 0.50
H7B 1.0645 0.4444 0.0117 0.048* 0.50
C8B 0.910 (4) 0.520 (2) −0.0647 (7) 0.046 (3) 0.50
H83 0.8243 0.5907 −0.0693 0.056* 0.50
H84 1.0109 0.5285 −0.0964 0.056* 0.50
C9B 0.797 (5) 0.401 (3) −0.0783 (13) 0.0651 (12) 0.50
H9B 0.6792 0.4034 −0.0527 0.078* 0.50
C10B 0.739 (4) 0.398 (4) −0.1495 (12) 0.104 (7) 0.50
H10D 0.6714 0.4726 −0.1601 0.156* 0.50
H10E 0.6568 0.3273 −0.1570 0.156* 0.50
H10F 0.8518 0.3907 −0.1756 0.156* 0.50
C11B 0.905 (9) 0.283 (3) −0.061 (3) 0.116 (7) 0.50
H11D 1.0278 0.2832 −0.0812 0.174* 0.50
H11E 0.8321 0.2123 −0.0743 0.174* 0.50
H11F 0.9217 0.2803 −0.0149 0.174* 0.50
H2N 0.780 (5) 0.611 (2) 0.042 (2) 0.139*
H6O 1.393 (6) 0.655 (3) −0.013 (3) 0.174*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
S1 0.0575 (4) 0.0422 (4) 0.0435 (4) −0.0031 (4) 0.0088 (4) 0.0032 (4)
O1 0.0808 (18) 0.107 (2) 0.096 (2) 0.0244 (16) 0.0092 (15) −0.0496 (17)
N1 0.0688 (18) 0.0496 (18) 0.0548 (19) 0.0067 (14) 0.0099 (16) −0.0070 (15)
C1 0.0542 (19) 0.0466 (19) 0.0328 (16) 0.0021 (16) 0.0081 (14) 0.0022 (14)
O2 0.0921 (16) 0.0889 (18) 0.0541 (14) 0.0387 (14) −0.0074 (14) 0.0009 (14)
N2 0.0490 (14) 0.0458 (15) 0.0351 (13) 0.0012 (11) 0.0038 (12) −0.0004 (11)
C2 0.0512 (17) 0.052 (2) 0.0349 (16) 0.0026 (16) 0.0075 (14) 0.0006 (15)
O3 0.0682 (14) 0.0802 (16) 0.0589 (13) −0.0165 (15) 0.0231 (11) −0.0023 (12)
C3 0.075 (2) 0.068 (2) 0.055 (2) −0.004 (2) 0.0129 (18) −0.019 (2)
O4 0.0946 (16) 0.0380 (13) 0.0574 (13) 0.0074 (10) 0.0061 (13) 0.0052 (11)
C4 0.062 (2) 0.106 (3) 0.070 (3) −0.012 (2) 0.005 (2) −0.034 (2)
O5 0.0464 (11) 0.0390 (13) 0.0661 (15) −0.0011 (9) 0.0019 (10) −0.0059 (11)
C5 0.058 (2) 0.108 (3) 0.061 (2) 0.012 (2) −0.0014 (18) −0.014 (2)
O6 0.0413 (13) 0.0466 (13) 0.0952 (17) 0.0033 (10) 0.0060 (12) −0.0068 (13)
C6 0.058 (2) 0.071 (2) 0.0417 (18) 0.0103 (17) 0.0038 (16) −0.0035 (16)
C12 0.0466 (16) 0.0431 (19) 0.0391 (17) 0.0025 (14) −0.0021 (15) −0.0025 (14)
C7A 0.0409 (15) 0.0398 (17) 0.0396 (15) −0.0010 (13) 0.0078 (12) −0.0005 (14)
C8A 0.053 (5) 0.042 (5) 0.044 (2) −0.005 (4) 0.008 (3) −0.009 (2)
C9A 0.085 (2) 0.058 (3) 0.052 (2) −0.029 (2) −0.0011 (19) −0.007 (2)
C10A 0.143 (16) 0.115 (10) 0.055 (9) −0.066 (13) −0.013 (10) −0.011 (6)
C11A 0.146 (4) 0.049 (5) 0.15 (2) −0.017 (5) −0.031 (13) −0.046 (7)
C7B 0.0409 (15) 0.0398 (17) 0.0396 (15) −0.0010 (13) 0.0078 (12) −0.0005 (14)
C8B 0.053 (5) 0.042 (5) 0.044 (2) −0.005 (4) 0.008 (3) −0.009 (2)
C9B 0.085 (2) 0.058 (3) 0.052 (2) −0.029 (2) −0.0011 (19) −0.007 (2)
C10B 0.143 (16) 0.115 (10) 0.055 (9) −0.066 (13) −0.013 (10) −0.011 (6)
C11B 0.146 (4) 0.049 (5) 0.15 (2) −0.017 (5) −0.031 (13) −0.046 (7)
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Geometric parameters (Å, º)

S1—O3 1.422 (2) C8A—C9A 1.532 (12)
S1—O4 1.424 (2) C8A—H81 0.9700
S1—N2 1.609 (2) C8A—H82 0.9700
S1—C1 1.781 (3) C9A—C11A 1.511 (13)
O1—N1 1.217 (3) C9A—C10A 1.531 (13)
N1—O2 1.211 (3) C9A—H9A 0.9800
N1—C2 1.466 (4) C10A—H10A 0.9600
C1—C6 1.376 (4) C10A—H10B 0.9600
C1—C2 1.408 (4) C10A—H10C 0.9600
N2—C7A 1.464 (3) C11A—H11A 0.9600
N2—H2N 0.850 (10) C11A—H11B 0.9600
C2—C3 1.372 (4) C11A—H11C 0.9600
C3—C4 1.369 (5) C8B—C9B 1.530 (11)
C3—H3 0.9300 C8B—H83 0.9700
C4—C5 1.360 (5) C8B—H84 0.9700
C4—H4 0.9300 C9B—C11B 1.513 (12)
O5—C12 1.212 (3) C9B—C10B 1.538 (14)
C5—C6 1.385 (4) C9B—H9B 0.9800
C5—H5 0.9300 C10B—H10D 0.9600
O6—C12 1.312 (3) C10B—H10E 0.9600
O6—H6O 0.852 (10) C10B—H10F 0.9600
C6—H6 0.9300 C11B—H11D 0.9600
C12—C7A 1.514 (4) C11B—H11E 0.9600
C7A—C8A 1.538 (11) C11B—H11F 0.9600
C7A—H7A 0.9800
O3—S1—O4 119.76 (13) N2—C7A—H7A 107.3
O3—S1—N2 108.02 (13) C12—C7A—H7A 107.3
O4—S1—N2 106.94 (13) C8A—C7A—H7A 107.3
O3—S1—C1 107.46 (13) C9A—C8A—C7A 113.8 (14)
O4—S1—C1 105.15 (14) C9A—C8A—H81 108.8
N2—S1—C1 109.20 (13) C7A—C8A—H81 108.8
O2—N1—O1 123.4 (3) C9A—C8A—H82 108.8
O2—N1—C2 118.7 (3) C7A—C8A—H82 108.8
O1—N1—C2 118.0 (3) H81—C8A—H82 107.7
C6—C1—C2 117.2 (3) C11A—C9A—C10A 112.0 (15)
C6—C1—S1 117.6 (2) C11A—C9A—C8A 111.0 (17)
C2—C1—S1 125.1 (2) C10A—C9A—C8A 111.0 (15)
C7A—N2—S1 120.39 (19) C11A—C9A—H9A 107.5
C7A—N2—H2N 115 (3) C10A—C9A—H9A 107.5
S1—N2—H2N 114 (3) C8A—C9A—H9A 107.5
C3—C2—C1 121.2 (3) C9B—C8B—H83 108.9
C3—C2—N1 116.5 (3) C9B—C8B—H84 108.9
C1—C2—N1 122.3 (3) H83—C8B—H84 107.7
C4—C3—C2 120.1 (3) C11B—C9B—C8B 113.7 (15)
C4—C3—H3 120.0 C11B—C9B—C10B 110.3 (16)
C2—C3—H3 120.0 C8B—C9B—C10B 109.5 (16)
C5—C4—C3 119.8 (4) C11B—C9B—H9B 107.7
C5—C4—H4 120.1 C8B—C9B—H9B 107.7
C3—C4—H4 120.1 C10B—C9B—H9B 107.7
C4—C5—C6 120.7 (3) C9B—C10B—H10D 109.5
C4—C5—H5 119.7 C9B—C10B—H10E 109.5
C6—C5—H5 119.7 H10D—C10B—H10E 109.5
C12—O6—H6O 111 (4) C9B—C10B—H10F 109.5
C1—C6—C5 121.0 (3) H10D—C10B—H10F 109.5
C1—C6—H6 119.5 H10E—C10B—H10F 109.5
C5—C6—H6 119.5 C9B—C11B—H11D 109.5
O5—C12—O6 123.0 (3) C9B—C11B—H11E 109.5
O5—C12—C7A 124.9 (3) H11D—C11B—H11E 109.5
O6—C12—C7A 112.0 (2) C9B—C11B—H11F 109.5
N2—C7A—C12 112.2 (2) H11D—C11B—H11F 109.5
N2—C7A—C8A 113.6 (10) H11E—C11B—H11F 109.5
C12—C7A—C8A 108.9 (9)
O3—S1—C1—C6 137.9 (2) C1—C2—C3—C4 1.9 (5)
O4—S1—C1—C6 9.3 (3) N1—C2—C3—C4 −177.2 (3)
N2—S1—C1—C6 −105.2 (2) C2—C3—C4—C5 −0.9 (5)
O3—S1—C1—C2 −36.9 (3) C3—C4—C5—C6 −0.1 (5)
O4—S1—C1—C2 −165.5 (2) C2—C1—C6—C5 0.7 (4)
N2—S1—C1—C2 80.0 (3) S1—C1—C6—C5 −174.5 (2)
O3—S1—N2—C7A −168.2 (2) C4—C5—C6—C1 0.2 (5)
O4—S1—N2—C7A −38.0 (2) S1—N2—C7A—C12 −88.8 (2)
C1—S1—N2—C7A 75.3 (2) S1—N2—C7A—C8A 147.2 (10)
C6—C1—C2—C3 −1.8 (4) O5—C12—C7A—N2 −32.7 (4)
S1—C1—C2—C3 173.0 (2) O6—C12—C7A—N2 149.8 (2)
C6—C1—C2—N1 177.3 (3) O5—C12—C7A—C8A 93.8 (11)
S1—C1—C2—N1 −7.9 (4) O6—C12—C7A—C8A −83.6 (11)
O2—N1—C2—C3 144.3 (3) N2—C7A—C8A—C9A −56 (2)
O1—N1—C2—C3 −35.4 (4) C12—C7A—C8A—C9A 177.8 (18)
O2—N1—C2—C1 −34.8 (4) C7A—C8A—C9A—C11A −80 (3)
O1—N1—C2—C1 145.5 (3) C7A—C8A—C9A—C10A 155 (2)
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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
N2—H2N···O2 0.85 (1) 2.34 (4) 2.937 (3) 128 (4)
O6—H6O···O5i 0.85 (1) 1.87 (2) 2.702 (3) 166 (5)
N2—H2N···O5ii 0.85 (1) 2.38 (2) 3.169 (3) 155 (4)
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Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) x−1/2, −y+3/2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5283).

References

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  2. Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
  3. Bruker (2007). SADABS, APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033260/ng5283sup1.cif

e-68-o2573-sup1.cif (25.6KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033260/ng5283Isup3.hkl

e-68-o2573-Isup3.hkl (134.1KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812033260/ng5283Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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