organic compounds
2-(4-Acetamidobenzenesulfonamido)-3-methylbutanoic acid
aMaterials Chemistry Laboratory, Department of Chemistry, Government College, University, Lahore 54000, Pakistan, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com
In the title compound, C13H18N2O5S, the benzene ring and the acetamide group are almost coplanar [dihedral angle = 5.6 (3)°], and the amine group projects almost vertically from this plane [C—C—S—N = −84.5 (7)°]. A short intramolecular C—H⋯O contact occurs. In the crystal, O—H⋯O, N—H⋯O and N—H⋯(O,O) hydrogen bonds lead to a three-dimensional network. One of the methyl groups of the isopropyl residue is disordered over two orientations in a 0.747 (16):0.253 (16) ratio.
Related literature
For background to the pharmacological uses of ); Mandell & Sande (1992). For related structures, see: Sharif et al. (2010); Khan et al. (2010).
see: Korolkovas (1988Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell 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 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536810016119/hb5434sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016119/hb5434Isup2.hkl
To 2-amino-3-methylbutanoic acid (0.339 g, 2.8 mmol ) in distilled water (10 ml) was added 4-acetylaminobenzenesulfonyl chloride (0.7 g, 2.8 mmol) with stirring at room temperature, while maintaining the pH of the reaction mixture at 8 using 3% sodium carbonate. The progress of the reaction was monitored by TLC. On completion of reaction, the pH was adjusted to 3.0 by slow addition 3 N HCl. The precipitate formed in this way was washed with water, dried and recrystalized from methanol and ethyl acetate mixture (50:50 v/v) to yield colourless prisms of (I); m. pt. 510 K.
The O- and C-bound H atoms were geometrically placed (O–H = 0.93 Å; C–H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2-1.5Ueq(O,C). The N-bound H atoms were refined with the distance restraint N–H = 0.86±0.01 Å, and with Uiso(H) = 1.2Ueq(N). High thermal motion was noted in the iso-propyl substituent and it proved possible to resolve two positions for one of the methyl groups. Anisotropic
(constrained to be equivalent for the components of the disorder by the EADP command in SHELXL-97) showed the major component of the disorder had a site occupancy factor = 0.747 (16). In the absence of significant effects, 1130 Friedel pairs were averaged in the final refinement.Sulfonamide drugs are widely used for the treatment of certain infections caused by Gram-positive and Gram-negative microorganisms, some fungi, and certain protozoa (Korolkovas, 1988; Mandell & Sande, 1992). In continuation of structural investigations of
(Sharif et al., 2010; Khan et al., 2010), herein, the of title compound, (I), is described.The structure analysis of (I), Fig. 1, shows that the acetamide group is co-planar with the benzene ring to which it is attached; the dihedral angle = 5.6 (3) °. This conformation is stabilised by an intramolecular C–H···O contact, Table 1. While the S atom also lies in this plane [the S1–C1–C2–C3 torsion angle = 176.8 (7) °], the sulfonamido-O atoms lie to one side [being displaced by 0.386 (5) Å for atom O1 and 0.555 (6) Å for O2] and the amine substituent to project almost vertically to the other [the N2–S1–C1–C2 torsion angle = -84.5 (7) °]. Within the amine group, the carboxylic acid group is folded back to lie over the benzene ring; the dihedral angle between the two planes = 34.2 (5) °.
The
is stabilised by O–H···O and N–H···O hydrogen bonding interactions, Table 1. Thus, the carboxylic acid-hydroxyl group forms a donor interaction to the amide-carbonyl, and each of the N—H atoms forms a donor interaction to a sulfonamido-O; an intramolecular interaction formed between the N2—H and carboxylic acid-carbonyl group is also noted, Table 1. The result of the hydrogen bonding just described is the formation of a 3-D network, Fig. 2.For background to the pharmacological uses of
see: Korolkovas (1988); Mandell & Sande (1992). For related structures, see: Sharif et al. (2010); Khan et al. (2010).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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C13H18N2O5S | F(000) = 664 |
Mr = 314.35 | Dx = 1.327 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 815 reflections |
a = 5.1649 (13) Å | θ = 3.0–18.5° |
b = 14.724 (5) Å | µ = 0.23 mm−1 |
c = 20.688 (7) Å | T = 293 K |
V = 1573.2 (8) Å3 | Prism, colourless |
Z = 4 | 0.39 × 0.09 × 0.07 mm |
Bruker APEXII CCD diffractometer | 1083 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.075 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
φ and ω scans | h = −6→5 |
7356 measured reflections | k = −14→17 |
1647 independent reflections | l = −24→24 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.209 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | w = 1/[σ2(Fo2) + (0.1138P)2] where P = (Fo2 + 2Fc2)/3 |
1647 reflections | (Δ/σ)max < 0.001 |
205 parameters | Δρmax = 0.49 e Å−3 |
2 restraints | Δρmin = −0.52 e Å−3 |
C13H18N2O5S | V = 1573.2 (8) Å3 |
Mr = 314.35 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.1649 (13) Å | µ = 0.23 mm−1 |
b = 14.724 (5) Å | T = 293 K |
c = 20.688 (7) Å | 0.39 × 0.09 × 0.07 mm |
Bruker APEXII CCD diffractometer | 1083 reflections with I > 2σ(I) |
7356 measured reflections | Rint = 0.075 |
1647 independent reflections |
R[F2 > 2σ(F2)] = 0.053 | 2 restraints |
wR(F2) = 0.209 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | Δρmax = 0.49 e Å−3 |
1647 reflections | Δρmin = −0.52 e Å−3 |
205 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | Occ. (<1) | |
S1 | 0.6472 (3) | 0.98522 (14) | 0.24127 (8) | 0.0374 (6) | |
O1 | 0.7761 (10) | 0.9900 (4) | 0.3028 (2) | 0.0474 (15) | |
O2 | 0.3793 (9) | 1.0094 (4) | 0.2371 (3) | 0.0484 (14) | |
O3 | 0.4852 (13) | 0.6006 (4) | 0.0597 (3) | 0.0627 (19) | |
O4 | 1.0931 (11) | 0.9940 (5) | 0.0904 (3) | 0.068 (2) | |
O5 | 0.7406 (11) | 0.9868 (5) | 0.0302 (3) | 0.0618 (19) | |
H5O | 0.8216 | 0.9540 | −0.0023 | 0.093* | |
N1 | 0.8024 (12) | 0.6160 (5) | 0.1338 (3) | 0.0423 (17) | |
H1N | 0.947 (8) | 0.593 (5) | 0.146 (4) | 0.051* | |
N2 | 0.8017 (12) | 1.0547 (4) | 0.1940 (3) | 0.0347 (15) | |
H2N | 0.963 (4) | 1.041 (5) | 0.194 (3) | 0.042* | |
C1 | 0.6850 (14) | 0.8749 (5) | 0.2107 (4) | 0.0341 (17) | |
C2 | 0.5207 (16) | 0.8443 (6) | 0.1626 (4) | 0.044 (2) | |
H2 | 0.3858 | 0.8810 | 0.1483 | 0.053* | |
C3 | 0.5570 (17) | 0.7596 (6) | 0.1360 (4) | 0.051 (2) | |
H3 | 0.4462 | 0.7395 | 0.1036 | 0.061* | |
C4 | 0.7560 (14) | 0.7038 (5) | 0.1568 (4) | 0.0381 (19) | |
C5 | 0.9198 (15) | 0.7362 (6) | 0.2053 (4) | 0.045 (2) | |
H5 | 1.0537 | 0.6994 | 0.2201 | 0.054* | |
C6 | 0.8875 (16) | 0.8207 (6) | 0.2314 (4) | 0.047 (2) | |
H6 | 1.0011 | 0.8417 | 0.2629 | 0.056* | |
C7 | 0.6686 (18) | 0.5689 (6) | 0.0892 (4) | 0.045 (2) | |
C8 | 0.7567 (19) | 0.4720 (5) | 0.0793 (4) | 0.057 (2) | |
H8A | 0.6125 | 0.4316 | 0.0850 | 0.086* | |
H8B | 0.8891 | 0.4575 | 0.1102 | 0.086* | |
H8C | 0.8245 | 0.4652 | 0.0364 | 0.086* | |
C9 | 0.7105 (16) | 1.0683 (6) | 0.1282 (3) | 0.0403 (19) | |
H9 | 0.5295 | 1.0486 | 0.1256 | 0.048* | |
C10 | 0.8709 (15) | 1.0112 (6) | 0.0812 (3) | 0.0429 (19) | |
C11 | 0.724 (2) | 1.1699 (7) | 0.1107 (5) | 0.071 (3) | 0.747 (16) |
H11 | 0.9013 | 1.1893 | 0.1209 | 0.086* | 0.747 (16) |
C12 | 0.550 (3) | 1.2240 (7) | 0.1542 (6) | 0.103 (5) | 0.747 (16) |
H12A | 0.5831 | 1.2876 | 0.1483 | 0.154* | 0.747 (16) |
H12B | 0.5821 | 1.2077 | 0.1984 | 0.154* | 0.747 (16) |
H12C | 0.3724 | 1.2113 | 0.1437 | 0.154* | 0.747 (16) |
C13 | 0.683 (4) | 1.1929 (11) | 0.0441 (7) | 0.109 (7) | 0.747 (16) |
H13A | 0.5309 | 1.1626 | 0.0286 | 0.164* | 0.747 (16) |
H13B | 0.8302 | 1.1742 | 0.0190 | 0.164* | 0.747 (16) |
H13C | 0.6608 | 1.2574 | 0.0402 | 0.164* | 0.747 (16) |
C11A | 0.724 (2) | 1.1699 (7) | 0.1107 (5) | 0.071 (3) | 0.253 (16) |
H11A | 0.6178 | 1.1695 | 0.0715 | 0.086* | 0.253 (16) |
C12A | 0.550 (3) | 1.2240 (7) | 0.1542 (6) | 0.103 (5) | 0.253 (16) |
H12D | 0.6523 | 1.2566 | 0.1851 | 0.154* | 0.253 (16) |
H12E | 0.4339 | 1.1837 | 0.1764 | 0.154* | 0.253 (16) |
H12F | 0.4513 | 1.2663 | 0.1288 | 0.154* | 0.253 (16) |
C13A | 0.928 (14) | 1.213 (3) | 0.088 (2) | 0.109 (7) | 0.253 (16) |
H13D | 0.9508 | 1.1990 | 0.0433 | 0.164* | 0.253 (16) |
H13E | 1.0795 | 1.1945 | 0.1118 | 0.164* | 0.253 (16) |
H13F | 0.9041 | 1.2774 | 0.0933 | 0.164* | 0.253 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0357 (10) | 0.0429 (11) | 0.0336 (9) | −0.0026 (9) | 0.0032 (8) | −0.0080 (8) |
O1 | 0.055 (3) | 0.058 (4) | 0.029 (3) | −0.006 (3) | −0.001 (2) | −0.008 (3) |
O2 | 0.032 (3) | 0.058 (4) | 0.055 (3) | 0.003 (3) | 0.006 (2) | −0.013 (3) |
O3 | 0.078 (4) | 0.049 (4) | 0.061 (4) | 0.014 (4) | −0.028 (4) | −0.016 (3) |
O4 | 0.047 (4) | 0.104 (6) | 0.054 (4) | 0.028 (4) | −0.001 (3) | −0.015 (4) |
O5 | 0.052 (4) | 0.080 (5) | 0.053 (3) | 0.006 (3) | −0.001 (3) | −0.034 (4) |
N1 | 0.045 (4) | 0.034 (4) | 0.048 (4) | 0.008 (3) | −0.007 (3) | −0.001 (3) |
N2 | 0.032 (4) | 0.033 (3) | 0.039 (3) | −0.002 (3) | 0.004 (3) | −0.002 (3) |
C1 | 0.031 (4) | 0.035 (4) | 0.036 (4) | −0.003 (3) | 0.000 (3) | −0.002 (3) |
C2 | 0.036 (4) | 0.040 (5) | 0.056 (5) | 0.005 (4) | −0.011 (4) | −0.006 (4) |
C3 | 0.048 (5) | 0.045 (5) | 0.059 (6) | 0.003 (4) | −0.020 (4) | −0.014 (5) |
C4 | 0.037 (4) | 0.034 (4) | 0.043 (4) | 0.004 (4) | 0.001 (4) | 0.000 (4) |
C5 | 0.044 (5) | 0.043 (5) | 0.047 (5) | 0.006 (4) | −0.013 (4) | 0.008 (4) |
C6 | 0.048 (5) | 0.047 (5) | 0.044 (5) | −0.003 (4) | −0.018 (4) | −0.004 (4) |
C7 | 0.060 (6) | 0.037 (5) | 0.038 (4) | −0.004 (4) | 0.006 (5) | −0.006 (4) |
C8 | 0.077 (6) | 0.039 (5) | 0.054 (5) | 0.010 (5) | −0.008 (5) | −0.011 (5) |
C9 | 0.042 (5) | 0.044 (5) | 0.035 (4) | 0.008 (4) | 0.006 (3) | −0.001 (4) |
C10 | 0.035 (5) | 0.049 (5) | 0.045 (4) | 0.000 (4) | 0.012 (4) | 0.004 (4) |
C11 | 0.108 (9) | 0.041 (6) | 0.064 (6) | 0.021 (6) | 0.020 (6) | 0.014 (5) |
C12 | 0.154 (13) | 0.053 (7) | 0.102 (9) | 0.052 (8) | 0.004 (9) | −0.011 (7) |
C13 | 0.21 (2) | 0.057 (9) | 0.064 (10) | 0.008 (12) | −0.005 (11) | 0.004 (8) |
C11A | 0.108 (9) | 0.041 (6) | 0.064 (6) | 0.021 (6) | 0.020 (6) | 0.014 (5) |
C12A | 0.154 (13) | 0.053 (7) | 0.102 (9) | 0.052 (8) | 0.004 (9) | −0.011 (7) |
C13A | 0.21 (2) | 0.057 (9) | 0.064 (10) | 0.008 (12) | −0.005 (11) | 0.004 (8) |
S1—O2 | 1.431 (5) | C8—H8B | 0.9600 |
S1—O1 | 1.438 (5) | C8—H8C | 0.9600 |
S1—N2 | 1.625 (6) | C9—C10 | 1.530 (10) |
S1—C1 | 1.754 (8) | C9—C11A | 1.541 (12) |
O3—C7 | 1.220 (10) | C9—C11 | 1.541 (12) |
O4—C10 | 1.191 (9) | C9—H9 | 0.9800 |
O5—C10 | 1.301 (9) | C11—C13 | 1.434 (17) |
O5—H5O | 0.9275 | C11—C12 | 1.503 (14) |
N1—C7 | 1.345 (10) | C11—H11 | 0.9800 |
N1—C4 | 1.398 (10) | C12—H12A | 0.9600 |
N1—H1N | 0.86 (5) | C12—H12B | 0.9600 |
N2—C9 | 1.454 (9) | C12—H12C | 0.9600 |
N2—H2N | 0.86 (3) | C13—H13A | 0.9600 |
C1—C6 | 1.383 (10) | C13—H13B | 0.9600 |
C1—C2 | 1.383 (10) | C13—H13C | 0.9600 |
C2—C3 | 1.377 (11) | C11A—C13A | 1.32 (7) |
C2—H2 | 0.9300 | C11A—C12A | 1.503 (14) |
C3—C4 | 1.385 (11) | C11A—H11A | 0.9800 |
C3—H3 | 0.9300 | C12A—H12D | 0.9600 |
C4—C5 | 1.395 (10) | C12A—H12E | 0.9600 |
C5—C6 | 1.368 (11) | C12A—H12F | 0.9600 |
C5—H5 | 0.9300 | C13A—H13D | 0.9600 |
C6—H6 | 0.9300 | C13A—H13E | 0.9600 |
C7—C8 | 1.512 (12) | C13A—H13F | 0.9600 |
C8—H8A | 0.9600 | ||
O2—S1—O1 | 119.3 (3) | H8A—C8—H8C | 109.5 |
O2—S1—N2 | 106.4 (4) | H8B—C8—H8C | 109.5 |
O1—S1—N2 | 105.9 (3) | N2—C9—C10 | 110.1 (6) |
O2—S1—C1 | 108.4 (3) | N2—C9—C11A | 109.8 (7) |
O1—S1—C1 | 108.2 (4) | C10—C9—C11A | 111.0 (7) |
N2—S1—C1 | 108.1 (3) | N2—C9—C11 | 109.8 (7) |
C10—O5—H5O | 119.8 | C10—C9—C11 | 111.0 (7) |
C7—N1—C4 | 128.6 (7) | N2—C9—H9 | 108.6 |
C7—N1—H1N | 116 (6) | C10—C9—H9 | 108.6 |
C4—N1—H1N | 114 (6) | C11A—C9—H9 | 108.6 |
C9—N2—S1 | 119.4 (5) | C11—C9—H9 | 108.6 |
C9—N2—H2N | 110 (5) | O4—C10—O5 | 124.8 (7) |
S1—N2—H2N | 109 (5) | O4—C10—C9 | 122.4 (8) |
C6—C1—C2 | 119.9 (7) | O5—C10—C9 | 112.8 (7) |
C6—C1—S1 | 120.4 (6) | C13—C11—C12 | 111.1 (12) |
C2—C1—S1 | 119.5 (6) | C13—C11—C9 | 116.7 (10) |
C1—C2—C3 | 119.9 (8) | C12—C11—C9 | 110.2 (9) |
C1—C2—H2 | 120.0 | C13—C11—H11 | 106.0 |
C3—C2—H2 | 120.0 | C12—C11—H11 | 106.0 |
C4—C3—C2 | 120.9 (8) | C9—C11—H11 | 106.0 |
C4—C3—H3 | 119.5 | C13A—C11A—C12A | 116 (2) |
C2—C3—H3 | 119.5 | C13A—C11A—C9 | 126 (3) |
C3—C4—C5 | 118.1 (7) | C12A—C11A—C9 | 110.2 (9) |
C3—C4—N1 | 124.7 (7) | C13A—C11A—H11A | 99.3 |
C5—C4—N1 | 117.2 (7) | C12A—C11A—H11A | 99.3 |
C6—C5—C4 | 121.4 (7) | C9—C11A—H11A | 99.3 |
C6—C5—H5 | 119.3 | C11A—C12A—H12D | 109.5 |
C4—C5—H5 | 119.3 | C11A—C12A—H12E | 109.5 |
C5—C6—C1 | 119.7 (7) | H12D—C12A—H12E | 109.5 |
C5—C6—H6 | 120.2 | C11A—C12A—H12F | 109.5 |
C1—C6—H6 | 120.2 | H12D—C12A—H12F | 109.5 |
O3—C7—N1 | 122.9 (8) | H12E—C12A—H12F | 109.5 |
O3—C7—C8 | 121.8 (8) | C11A—C13A—H13D | 109.5 |
N1—C7—C8 | 115.2 (8) | C11A—C13A—H13E | 109.5 |
C7—C8—H8A | 109.5 | H13D—C13A—H13E | 109.5 |
C7—C8—H8B | 109.5 | C11A—C13A—H13F | 109.5 |
H8A—C8—H8B | 109.5 | H13D—C13A—H13F | 109.5 |
C7—C8—H8C | 109.5 | H13E—C13A—H13F | 109.5 |
O2—S1—N2—C9 | −49.5 (6) | C4—N1—C7—C8 | −174.9 (8) |
O1—S1—N2—C9 | −177.4 (6) | S1—N2—C9—C10 | −99.4 (7) |
C1—S1—N2—C9 | 66.8 (6) | S1—N2—C9—C11A | 138.0 (7) |
O2—S1—C1—C6 | −153.6 (6) | S1—N2—C9—C11 | 138.0 (7) |
O1—S1—C1—C6 | −22.9 (7) | N2—C9—C10—O4 | −31.3 (11) |
N2—S1—C1—C6 | 91.4 (7) | C11A—C9—C10—O4 | 90.5 (11) |
O2—S1—C1—C2 | 30.5 (7) | C11—C9—C10—O4 | 90.5 (11) |
O1—S1—C1—C2 | 161.2 (6) | N2—C9—C10—O5 | 150.7 (7) |
N2—S1—C1—C2 | −84.5 (7) | C11A—C9—C10—O5 | −87.5 (9) |
C6—C1—C2—C3 | 0.8 (12) | C11—C9—C10—O5 | −87.5 (9) |
S1—C1—C2—C3 | 176.7 (7) | N2—C9—C11—C13 | 169.7 (13) |
C1—C2—C3—C4 | 0.2 (13) | C10—C9—C11—C13 | 47.7 (16) |
C2—C3—C4—C5 | −0.4 (13) | C11A—C9—C11—C13 | 0 (100) |
C2—C3—C4—N1 | 178.2 (8) | N2—C9—C11—C12 | −62.3 (12) |
C7—N1—C4—C3 | −0.9 (13) | C10—C9—C11—C12 | 175.7 (9) |
C7—N1—C4—C5 | 177.7 (8) | C11A—C9—C11—C12 | 0 (100) |
C3—C4—C5—C6 | −0.5 (12) | N2—C9—C11A—C13A | 85 (3) |
N1—C4—C5—C6 | −179.2 (7) | C10—C9—C11A—C13A | −37 (3) |
C4—C5—C6—C1 | 1.5 (12) | C11—C9—C11A—C13A | 0 (100) |
C2—C1—C6—C5 | −1.7 (12) | N2—C9—C11A—C12A | −62.3 (12) |
S1—C1—C6—C5 | −177.6 (6) | C10—C9—C11A—C12A | 175.7 (9) |
C4—N1—C7—O3 | 3.5 (13) | C11—C9—C11A—C12A | 0 (100) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O3 | 0.93 | 2.25 | 2.848 (11) | 122 |
O5—H5o···O3i | 0.93 | 1.66 | 2.591 (9) | 176 |
N1—H1n···O1ii | 0.86 (5) | 2.34 (7) | 3.147 (9) | 157 (6) |
N2—H2n···O2iii | 0.86 (3) | 2.37 (3) | 3.184 (8) | 158 (6) |
N2—H2n···O4 | 0.86 (3) | 2.35 (6) | 2.767 (9) | 110 (5) |
Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x+2, y−1/2, −z+1/2; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C13H18N2O5S |
Mr | 314.35 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 5.1649 (13), 14.724 (5), 20.688 (7) |
V (Å3) | 1573.2 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.39 × 0.09 × 0.07 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7356, 1647, 1083 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.209, 1.16 |
No. of reflections | 1647 |
No. of parameters | 205 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.49, −0.52 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O3 | 0.93 | 2.25 | 2.848 (11) | 122 |
O5—H5o···O3i | 0.93 | 1.66 | 2.591 (9) | 176 |
N1—H1n···O1ii | 0.86 (5) | 2.34 (7) | 3.147 (9) | 157 (6) |
N2—H2n···O2iii | 0.86 (3) | 2.37 (3) | 3.184 (8) | 158 (6) |
N2—H2n···O4 | 0.86 (3) | 2.35 (6) | 2.767 (9) | 110 (5) |
Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x+2, y−1/2, −z+1/2; (iii) x+1, y, z. |
Footnotes
‡Additional correspondence author, e-mail: iuklodhi@yahoo.com.
Acknowledgements
We are grateful to Mr Munawar Hussain, Engineering Cell GC University, Lahore, for providing support services to the Materials Chemistry Laboratory.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Sulfonamide drugs are widely used for the treatment of certain infections caused by Gram-positive and Gram-negative microorganisms, some fungi, and certain protozoa (Korolkovas, 1988; Mandell & Sande, 1992). In continuation of structural investigations of sulfonamides (Sharif et al., 2010; Khan et al., 2010), herein, the crystal structure of title compound, (I), is described.
The structure analysis of (I), Fig. 1, shows that the acetamide group is co-planar with the benzene ring to which it is attached; the dihedral angle = 5.6 (3) °. This conformation is stabilised by an intramolecular C–H···O contact, Table 1. While the S atom also lies in this plane [the S1–C1–C2–C3 torsion angle = 176.8 (7) °], the sulfonamido-O atoms lie to one side [being displaced by 0.386 (5) Å for atom O1 and 0.555 (6) Å for O2] and the amine substituent to project almost vertically to the other [the N2–S1–C1–C2 torsion angle = -84.5 (7) °]. Within the amine group, the carboxylic acid group is folded back to lie over the benzene ring; the dihedral angle between the two planes = 34.2 (5) °.
The crystal structure is stabilised by O–H···O and N–H···O hydrogen bonding interactions, Table 1. Thus, the carboxylic acid-hydroxyl group forms a donor interaction to the amide-carbonyl, and each of the N—H atoms forms a donor interaction to a sulfonamido-O; an intramolecular interaction formed between the N2—H and carboxylic acid-carbonyl group is also noted, Table 1. The result of the hydrogen bonding just described is the formation of a 3-D network, Fig. 2.