organic compounds
2-Benzenesulfonamido-3-methylbutyric acid
aCenter of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, bDepartment of Chemistry, University of Gujrat, Gujrat 50781, Pakistan, cDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and dDepartment of Chemistry, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia
*Correspondence e-mail: mnachemist@hotmail.com, muhammad.danish@uog.edu.pk
In the 11H15NO4S, two independent molecules are present per they are dimerized through O—H⋯O hydrogen bonds between their carboxy groups to generate R22(8) loops. An intramolecular N—H⋯O link in one of the molecules closes an S(5) ring. The dimers are linked by N—H⋯O and C—H⋯O hydrogen bonds to form a three-dimensional network. The C atoms of the isopropyl group of one of the molecules are disordered over two orientations in a 3:1 ratio.
of the title compound, CRelated literature
For biological studies of et al. (2007). For related structures, see: Khan et al. (2011); Arshad et al. (2012). For graph-set notation, see: Bernstein et al. (1995).
see: NalamExperimental
Crystal data
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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: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and X-SEED (Barbour, 2001).
Supporting information
10.1107/S1600536812034393/hb6922sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812034393/hb6922Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812034393/hb6922Isup3.cml
L-Valine (0.50 g, 0.043 mmole) dissolved in 12-15 mL distilled water using sodium carbonate (1M) to a pH of 8–9. Benzenesulphonyl chloride (0.75 g, 0.043 mmole) added within 3–5 min. The pH was adjusted by sodium carbonate (1M). Disappearance of suspended benzenesulfonyl chloride gave indication of completion of reaction. Then, dilute HCl was added dropwise to result in a pH 2–3. The precipitate was filtered, washed with plenty of water and dried. Colourless prisms were obtained upon recrystalization from methanol solution.
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 = 0.98 Å for tertiary, and were refined using a riding model with Uiso(H) = 1.2 Ueq(C) for aromatic & tertiary and Uiso(H) = 1.5 Ueq(C) for methyl carbon atoms.
The N—H = 0.81–0.82 (5) and O—H = 0.85—0.86 (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
of product, and the is that of the reactant (L-Valine).The atoms C9—C11 were disordered over two positions with the occupancies of 0.75 for C9A—C11A and 0.25 for C9B—C11B. The temperature factors of pairs of atoms were restrained to be identical.
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: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and X-SEED (Barbour, 2001).Fig. 1. The labelled molecular structure of (I) with 50% displacement ellipsoids, showing intramolecular hydrogen bonding and formation of dimers through carboxylic group using dashed lines. | |
Fig. 2. Unit cell packing showes intermolecular interactions using dashed lines. |
C11H15NO4S | F(000) = 544 |
Mr = 257.30 | Dx = 1.296 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 4554 reflections |
a = 5.4954 (3) Å | θ = 2.6–24.4° |
b = 15.5097 (10) Å | µ = 0.25 mm−1 |
c = 15.5106 (9) Å | T = 296 K |
β = 94.043 (3)° | Prismatic, colorless |
V = 1318.71 (14) Å3 | 0.37 × 0.22 × 0.18 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 4203 independent reflections |
Radiation source: fine-focus sealed tube | 3803 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −5→6 |
Tmin = 0.914, Tmax = 0.957 | k = −15→18 |
9573 measured reflections | l = −18→18 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0543P)2 + 0.0931P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.093 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.18 e Å−3 |
4203 reflections | Δρmin = −0.18 e Å−3 |
335 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
7 restraints | Extinction coefficient: 0.0039 (11) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1785 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.00 (6) |
C11H15NO4S | V = 1318.71 (14) Å3 |
Mr = 257.30 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.4954 (3) Å | µ = 0.25 mm−1 |
b = 15.5097 (10) Å | T = 296 K |
c = 15.5106 (9) Å | 0.37 × 0.22 × 0.18 mm |
β = 94.043 (3)° |
Bruker Kappa APEXII CCD diffractometer | 4203 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 3803 reflections with I > 2σ(I) |
Tmin = 0.914, Tmax = 0.957 | Rint = 0.023 |
9573 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | Δρmax = 0.18 e Å−3 |
S = 1.05 | Δρmin = −0.18 e Å−3 |
4203 reflections | Absolute structure: Flack (1983), 1785 Friedel pairs |
335 parameters | Absolute structure parameter: 0.00 (6) |
7 restraints |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.01018 (13) | 0.47881 (5) | 0.94705 (4) | 0.0526 (2) | |
S2 | 0.63466 (11) | 0.90716 (5) | 0.55510 (4) | 0.04379 (18) | |
O1 | −0.2265 (4) | 0.50382 (18) | 0.97036 (13) | 0.0746 (7) | |
O2 | 0.1285 (5) | 0.40489 (17) | 0.98428 (14) | 0.0812 (7) | |
O3 | 0.3451 (4) | 0.64351 (16) | 0.82551 (15) | 0.0762 (7) | |
O4 | 0.0009 (5) | 0.7191 (2) | 0.82050 (16) | 0.0896 (9) | |
O5 | 0.4720 (4) | 0.94893 (15) | 0.49394 (12) | 0.0615 (6) | |
O6 | 0.8908 (3) | 0.91930 (15) | 0.55236 (12) | 0.0583 (5) | |
O7 | 0.0874 (3) | 0.74580 (16) | 0.65554 (14) | 0.0683 (6) | |
O8 | 0.4671 (4) | 0.69767 (18) | 0.67244 (14) | 0.0713 (7) | |
N1 | 0.1901 (4) | 0.55941 (18) | 0.97225 (14) | 0.0519 (6) | |
N2 | 0.5961 (4) | 0.80431 (17) | 0.54293 (14) | 0.0470 (6) | |
C1 | −0.0023 (4) | 0.4673 (2) | 0.83346 (15) | 0.0478 (7) | |
C2 | −0.1899 (5) | 0.5045 (2) | 0.78370 (19) | 0.0642 (9) | |
H2 | −0.3146 | 0.5332 | 0.8094 | 0.077* | |
C3 | −0.1909 (7) | 0.4988 (3) | 0.6954 (2) | 0.0783 (11) | |
H3 | −0.3168 | 0.5243 | 0.6611 | 0.094* | |
C4 | −0.0131 (7) | 0.4572 (3) | 0.6580 (2) | 0.0799 (11) | |
H4 | −0.0170 | 0.4533 | 0.5980 | 0.096* | |
C5 | 0.1747 (7) | 0.4201 (3) | 0.7076 (2) | 0.0877 (13) | |
H5 | 0.2987 | 0.3916 | 0.6814 | 0.105* | |
C6 | 0.1802 (6) | 0.4251 (3) | 0.7962 (2) | 0.0721 (10) | |
H6 | 0.3070 | 0.4000 | 0.8303 | 0.087* | |
C7 | 0.1146 (7) | 0.6464 (2) | 0.95050 (19) | 0.0640 (8) | |
H7 | −0.0636 | 0.6460 | 0.9511 | 0.077* | |
C8 | 0.1658 (6) | 0.6696 (2) | 0.8590 (2) | 0.0598 (8) | |
C9A | 0.2016 (11) | 0.7179 (4) | 1.0149 (3) | 0.0846 (16) | 0.75 |
H9A | 0.1325 | 0.7736 | 0.9960 | 0.102* | 0.75 |
C9B | 0.336 (5) | 0.6908 (11) | 1.0186 (10) | 0.0846 (16) | 0.25 |
H9B | 0.4889 | 0.6580 | 1.0183 | 0.102* | 0.25 |
C10A | 0.1194 (16) | 0.6948 (6) | 1.1039 (4) | 0.1206 (18) | 0.75 |
H10A | 0.1968 | 0.6422 | 1.1235 | 0.181* | 0.75 |
H10B | −0.0544 | 0.6874 | 1.1004 | 0.181* | 0.75 |
H10C | 0.1642 | 0.7403 | 1.1439 | 0.181* | 0.75 |
C10B | 0.252 (4) | 0.699 (2) | 1.1091 (11) | 0.132 (8) | 0.25 |
H10D | 0.3754 | 0.7273 | 1.1455 | 0.198* | 0.25 |
H10E | 0.2248 | 0.6420 | 1.1317 | 0.198* | 0.25 |
H10F | 0.1035 | 0.7311 | 1.1075 | 0.198* | 0.25 |
C11A | 0.4800 (14) | 0.7213 (6) | 1.0175 (5) | 0.1206 (18) | 0.75 |
H11A | 0.5307 | 0.7257 | 0.9597 | 0.181* | 0.75 |
H11B | 0.5466 | 0.6698 | 1.0441 | 0.181* | 0.75 |
H11C | 0.5375 | 0.7706 | 1.0504 | 0.181* | 0.75 |
C11B | 0.366 (4) | 0.7811 (13) | 0.9824 (12) | 0.132 (8) | 0.25 |
H11D | 0.4428 | 0.8176 | 1.0264 | 0.198* | 0.25 |
H11E | 0.2083 | 0.8041 | 0.9643 | 0.198* | 0.25 |
H11F | 0.4648 | 0.7787 | 0.9339 | 0.198* | 0.25 |
C12 | 0.5515 (5) | 0.93452 (19) | 0.65875 (17) | 0.0517 (7) | |
C13 | 0.6936 (7) | 0.9040 (3) | 0.72930 (18) | 0.0840 (11) | |
H13 | 0.8328 | 0.8715 | 0.7219 | 0.101* | |
C14 | 0.6242 (12) | 0.9230 (4) | 0.8109 (2) | 0.1203 (18) | |
H14 | 0.7154 | 0.9018 | 0.8591 | 0.144* | |
C15 | 0.4279 (12) | 0.9714 (5) | 0.8216 (3) | 0.135 (2) | |
H15 | 0.3843 | 0.9836 | 0.8771 | 0.162* | |
C16 | 0.2912 (8) | 1.0028 (4) | 0.7526 (4) | 0.130 (2) | |
H16 | 0.1549 | 1.0364 | 0.7613 | 0.156* | |
C17 | 0.3527 (6) | 0.9852 (3) | 0.6681 (3) | 0.0889 (12) | |
H17 | 0.2615 | 1.0073 | 0.6203 | 0.107* | |
C18 | 0.3522 (4) | 0.76567 (19) | 0.53994 (17) | 0.0444 (6) | |
H18 | 0.2335 | 0.8099 | 0.5203 | 0.053* | |
C19 | 0.2898 (5) | 0.7353 (2) | 0.62866 (19) | 0.0515 (7) | |
C20 | 0.3346 (5) | 0.6908 (2) | 0.4741 (2) | 0.0617 (8) | |
H20 | 0.4612 | 0.6485 | 0.4915 | 0.074* | |
C21 | 0.3830 (8) | 0.7240 (3) | 0.3847 (2) | 0.0929 (13) | |
H21A | 0.3896 | 0.6763 | 0.3455 | 0.139* | |
H21B | 0.5357 | 0.7543 | 0.3875 | 0.139* | |
H21C | 0.2542 | 0.7624 | 0.3646 | 0.139* | |
C22 | 0.0909 (7) | 0.6464 (3) | 0.4729 (3) | 0.1032 (15) | |
H22A | −0.0359 | 0.6867 | 0.4557 | 0.155* | |
H22B | 0.0657 | 0.6249 | 0.5296 | 0.155* | |
H22C | 0.0873 | 0.5993 | 0.4327 | 0.155* | |
H1N | 0.329 (8) | 0.544 (4) | 0.967 (3) | 0.124* | |
H2N | 0.701 (8) | 0.775 (4) | 0.569 (3) | 0.124* | |
H4O | 0.016 (10) | 0.736 (4) | 0.7683 (15) | 0.155* | |
H8O | 0.423 (9) | 0.676 (4) | 0.719 (2) | 0.155* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0641 (4) | 0.0565 (5) | 0.0374 (3) | −0.0096 (3) | 0.0055 (3) | 0.0090 (3) |
S2 | 0.0456 (3) | 0.0506 (4) | 0.0350 (3) | −0.0056 (3) | 0.0010 (2) | 0.0099 (3) |
O1 | 0.0674 (13) | 0.110 (2) | 0.0498 (11) | −0.0205 (12) | 0.0258 (10) | −0.0023 (12) |
O2 | 0.1254 (19) | 0.0546 (14) | 0.0609 (12) | −0.0055 (15) | −0.0131 (12) | 0.0208 (12) |
O3 | 0.0810 (14) | 0.0791 (18) | 0.0719 (14) | 0.0184 (13) | 0.0298 (12) | 0.0299 (13) |
O4 | 0.0912 (17) | 0.104 (2) | 0.0765 (16) | 0.0295 (15) | 0.0289 (14) | 0.0358 (16) |
O5 | 0.0675 (12) | 0.0630 (14) | 0.0517 (11) | −0.0038 (10) | −0.0127 (9) | 0.0186 (9) |
O6 | 0.0503 (10) | 0.0710 (16) | 0.0540 (10) | −0.0132 (10) | 0.0062 (8) | 0.0129 (10) |
O7 | 0.0496 (11) | 0.0854 (17) | 0.0726 (14) | 0.0144 (10) | 0.0227 (10) | 0.0315 (12) |
O8 | 0.0566 (12) | 0.0935 (19) | 0.0656 (14) | 0.0184 (12) | 0.0166 (10) | 0.0356 (13) |
N1 | 0.0609 (13) | 0.0558 (17) | 0.0387 (11) | −0.0016 (12) | 0.0024 (10) | 0.0051 (11) |
N2 | 0.0405 (11) | 0.0574 (17) | 0.0440 (12) | −0.0009 (10) | 0.0088 (9) | 0.0049 (11) |
C1 | 0.0488 (14) | 0.0562 (19) | 0.0386 (13) | −0.0048 (13) | 0.0049 (11) | −0.0002 (13) |
C2 | 0.0537 (16) | 0.091 (3) | 0.0480 (15) | 0.0123 (15) | 0.0015 (13) | −0.0100 (15) |
C3 | 0.082 (2) | 0.105 (3) | 0.0460 (16) | 0.012 (2) | −0.0087 (15) | −0.0079 (18) |
C4 | 0.091 (2) | 0.104 (3) | 0.0449 (16) | −0.009 (2) | 0.0090 (17) | −0.0220 (18) |
C5 | 0.083 (2) | 0.111 (4) | 0.071 (2) | 0.014 (2) | 0.0245 (19) | −0.028 (2) |
C6 | 0.0671 (18) | 0.084 (3) | 0.0648 (19) | 0.0208 (18) | 0.0004 (15) | −0.0091 (17) |
C7 | 0.084 (2) | 0.055 (2) | 0.0549 (17) | −0.0038 (16) | 0.0198 (15) | 0.0013 (15) |
C8 | 0.0667 (19) | 0.056 (2) | 0.0592 (17) | 0.0038 (15) | 0.0203 (15) | 0.0137 (15) |
C9A | 0.118 (5) | 0.060 (4) | 0.076 (3) | 0.017 (3) | 0.008 (3) | −0.017 (3) |
C9B | 0.118 (5) | 0.060 (4) | 0.076 (3) | 0.017 (3) | 0.008 (3) | −0.017 (3) |
C10A | 0.145 (5) | 0.124 (5) | 0.092 (3) | −0.026 (4) | 0.001 (3) | −0.035 (3) |
C10B | 0.138 (15) | 0.163 (17) | 0.094 (9) | −0.098 (14) | 0.000 (9) | −0.032 (10) |
C11A | 0.145 (5) | 0.124 (5) | 0.092 (3) | −0.026 (4) | 0.001 (3) | −0.035 (3) |
C11B | 0.138 (15) | 0.163 (17) | 0.094 (9) | −0.098 (14) | 0.000 (9) | −0.032 (10) |
C12 | 0.0509 (15) | 0.059 (2) | 0.0456 (15) | −0.0092 (13) | 0.0033 (12) | −0.0048 (13) |
C13 | 0.111 (3) | 0.100 (3) | 0.0396 (15) | 0.019 (3) | −0.0019 (16) | 0.0004 (19) |
C14 | 0.175 (5) | 0.148 (5) | 0.0382 (19) | −0.020 (4) | 0.007 (2) | −0.016 (3) |
C15 | 0.140 (4) | 0.196 (7) | 0.074 (3) | −0.052 (5) | 0.044 (3) | −0.075 (4) |
C16 | 0.076 (3) | 0.196 (7) | 0.122 (4) | −0.007 (3) | 0.031 (3) | −0.090 (4) |
C17 | 0.0591 (19) | 0.120 (4) | 0.086 (2) | 0.007 (2) | −0.0036 (17) | −0.041 (3) |
C18 | 0.0423 (13) | 0.0456 (17) | 0.0457 (14) | −0.0035 (12) | 0.0057 (11) | 0.0087 (12) |
C19 | 0.0486 (15) | 0.0491 (18) | 0.0579 (17) | 0.0040 (13) | 0.0118 (13) | 0.0099 (13) |
C20 | 0.0570 (17) | 0.055 (2) | 0.072 (2) | 0.0017 (15) | 0.0021 (14) | −0.0047 (16) |
C21 | 0.121 (3) | 0.101 (4) | 0.055 (2) | −0.006 (3) | −0.002 (2) | −0.023 (2) |
C22 | 0.086 (3) | 0.076 (3) | 0.147 (4) | −0.022 (2) | 0.004 (3) | −0.030 (3) |
S1—O2 | 1.420 (3) | C9B—C11B | 1.522 (10) |
S1—O1 | 1.428 (2) | C9B—H9B | 0.9800 |
S1—N1 | 1.624 (3) | C10A—H10A | 0.9600 |
S1—C1 | 1.767 (2) | C10A—H10B | 0.9600 |
S2—O5 | 1.414 (2) | C10A—H10C | 0.9600 |
S2—O6 | 1.4239 (19) | C10B—H10D | 0.9600 |
S2—N2 | 1.619 (3) | C10B—H10E | 0.9600 |
S2—C12 | 1.754 (3) | C10B—H10F | 0.9600 |
O3—C8 | 1.215 (4) | C11A—H11A | 0.9600 |
O4—C8 | 1.300 (4) | C11A—H11B | 0.9600 |
O4—H4O | 0.859 (10) | C11A—H11C | 0.9600 |
O7—C19 | 1.226 (3) | C11B—H11D | 0.9600 |
O8—C19 | 1.288 (3) | C11B—H11E | 0.9600 |
O8—H8O | 0.849 (10) | C11B—H11F | 0.9600 |
N1—C7 | 1.445 (4) | C12—C17 | 1.362 (5) |
N1—H1N | 0.81 (5) | C12—C13 | 1.382 (4) |
N2—C18 | 1.466 (3) | C13—C14 | 1.379 (6) |
N2—H2N | 0.82 (5) | C13—H13 | 0.9300 |
C1—C6 | 1.359 (4) | C14—C15 | 1.334 (8) |
C1—C2 | 1.371 (4) | C14—H14 | 0.9300 |
C2—C3 | 1.373 (4) | C15—C16 | 1.354 (8) |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
C3—C4 | 1.338 (5) | C16—C17 | 1.403 (6) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.370 (5) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—C19 | 1.516 (4) |
C5—C6 | 1.375 (5) | C18—C20 | 1.545 (4) |
C5—H5 | 0.9300 | C18—H18 | 0.9800 |
C6—H6 | 0.9300 | C20—C22 | 1.505 (5) |
C7—C8 | 1.510 (4) | C20—C21 | 1.521 (5) |
C7—C9A | 1.545 (6) | C20—H20 | 0.9800 |
C7—C9B | 1.70 (2) | C21—H21A | 0.9600 |
C7—H7 | 0.9800 | C21—H21B | 0.9600 |
C9A—C10A | 1.526 (7) | C21—H21C | 0.9600 |
C9A—C11A | 1.528 (7) | C22—H22A | 0.9600 |
C9A—H9A | 0.9800 | C22—H22B | 0.9600 |
C9B—C10B | 1.513 (10) | C22—H22C | 0.9600 |
O2—S1—O1 | 121.01 (16) | C10B—C9B—H9B | 111.3 |
O2—S1—N1 | 105.66 (14) | C11B—C9B—H9B | 111.3 |
O1—S1—N1 | 106.25 (15) | C7—C9B—H9B | 111.3 |
O2—S1—C1 | 107.95 (15) | C9B—C10B—H10D | 109.5 |
O1—S1—C1 | 107.93 (13) | C9B—C10B—H10E | 109.5 |
N1—S1—C1 | 107.33 (12) | H10D—C10B—H10E | 109.5 |
O5—S2—O6 | 119.94 (12) | C9B—C10B—H10F | 109.5 |
O5—S2—N2 | 107.56 (13) | H10D—C10B—H10F | 109.5 |
O6—S2—N2 | 104.39 (12) | H10E—C10B—H10F | 109.5 |
O5—S2—C12 | 108.11 (14) | C9B—C11B—H11D | 109.5 |
O6—S2—C12 | 108.50 (12) | C9B—C11B—H11E | 109.5 |
N2—S2—C12 | 107.75 (13) | H11D—C11B—H11E | 109.5 |
C8—O4—H4O | 120 (4) | C9B—C11B—H11F | 109.5 |
C19—O8—H8O | 112 (4) | H11D—C11B—H11F | 109.5 |
C7—N1—S1 | 120.2 (2) | H11E—C11B—H11F | 109.5 |
C7—N1—H1N | 121 (4) | C17—C12—C13 | 121.8 (3) |
S1—N1—H1N | 108 (4) | C17—C12—S2 | 120.0 (2) |
C18—N2—S2 | 121.25 (18) | C13—C12—S2 | 118.3 (2) |
C18—N2—H2N | 114 (4) | C14—C13—C12 | 118.4 (4) |
S2—N2—H2N | 114 (4) | C14—C13—H13 | 120.8 |
C6—C1—C2 | 120.7 (3) | C12—C13—H13 | 120.8 |
C6—C1—S1 | 119.6 (2) | C15—C14—C13 | 120.8 (5) |
C2—C1—S1 | 119.6 (2) | C15—C14—H14 | 119.6 |
C1—C2—C3 | 119.0 (3) | C13—C14—H14 | 119.6 |
C1—C2—H2 | 120.5 | C14—C15—C16 | 120.8 (4) |
C3—C2—H2 | 120.5 | C14—C15—H15 | 119.6 |
C4—C3—C2 | 120.8 (3) | C16—C15—H15 | 119.6 |
C4—C3—H3 | 119.6 | C15—C16—C17 | 120.8 (5) |
C2—C3—H3 | 119.6 | C15—C16—H16 | 119.6 |
C3—C4—C5 | 120.2 (3) | C17—C16—H16 | 119.6 |
C3—C4—H4 | 119.9 | C12—C17—C16 | 117.3 (4) |
C5—C4—H4 | 119.9 | C12—C17—H17 | 121.3 |
C4—C5—C6 | 120.1 (3) | C16—C17—H17 | 121.3 |
C4—C5—H5 | 120.0 | N2—C18—C19 | 111.3 (2) |
C6—C5—H5 | 120.0 | N2—C18—C20 | 110.1 (2) |
C1—C6—C5 | 119.2 (3) | C19—C18—C20 | 111.0 (3) |
C1—C6—H6 | 120.4 | N2—C18—H18 | 108.1 |
C5—C6—H6 | 120.4 | C19—C18—H18 | 108.1 |
N1—C7—C8 | 111.9 (3) | C20—C18—H18 | 108.1 |
N1—C7—C9A | 116.7 (3) | O7—C19—O8 | 123.5 (3) |
C8—C7—C9A | 111.5 (3) | O7—C19—C18 | 122.4 (2) |
N1—C7—C9B | 93.0 (6) | O8—C19—C18 | 114.1 (2) |
C8—C7—C9B | 108.3 (6) | C22—C20—C21 | 110.9 (3) |
C9A—C7—C9B | 29.9 (6) | C22—C20—C18 | 111.5 (3) |
N1—C7—H7 | 105.2 | C21—C20—C18 | 109.9 (3) |
C8—C7—H7 | 105.2 | C22—C20—H20 | 108.1 |
C9A—C7—H7 | 105.2 | C21—C20—H20 | 108.1 |
C9B—C7—H7 | 132.1 | C18—C20—H20 | 108.1 |
O3—C8—O4 | 124.1 (3) | C20—C21—H21A | 109.5 |
O3—C8—C7 | 122.2 (3) | C20—C21—H21B | 109.5 |
O4—C8—C7 | 113.7 (3) | H21A—C21—H21B | 109.5 |
C10A—C9A—C11A | 110.1 (6) | C20—C21—H21C | 109.5 |
C10A—C9A—C7 | 108.6 (5) | H21A—C21—H21C | 109.5 |
C11A—C9A—C7 | 107.8 (5) | H21B—C21—H21C | 109.5 |
C10A—C9A—H9A | 110.1 | C20—C22—H22A | 109.5 |
C11A—C9A—H9A | 110.1 | C20—C22—H22B | 109.5 |
C7—C9A—H9A | 110.1 | H22A—C22—H22B | 109.5 |
C10B—C9B—C11B | 108.4 (17) | C20—C22—H22C | 109.5 |
C10B—C9B—C7 | 110.8 (17) | H22A—C22—H22C | 109.5 |
C11B—C9B—C7 | 103.5 (14) | H22B—C22—H22C | 109.5 |
O2—S1—N1—C7 | −174.7 (2) | C8—C7—C9A—C11A | −66.9 (6) |
O1—S1—N1—C7 | −45.0 (2) | C9B—C7—C9A—C11A | 22.7 (11) |
C1—S1—N1—C7 | 70.3 (2) | N1—C7—C9B—C10B | −86.3 (18) |
O5—S2—N2—C18 | −50.0 (2) | C8—C7—C9B—C10B | 159.4 (17) |
O6—S2—N2—C18 | −178.45 (19) | C9A—C7—C9B—C10B | 58 (2) |
C12—S2—N2—C18 | 66.3 (2) | N1—C7—C9B—C11B | 157.6 (14) |
O2—S1—C1—C6 | −32.5 (3) | C8—C7—C9B—C11B | 43.4 (15) |
O1—S1—C1—C6 | −164.8 (3) | C9A—C7—C9B—C11B | −58.1 (13) |
N1—S1—C1—C6 | 81.0 (3) | O5—S2—C12—C17 | 2.4 (3) |
O2—S1—C1—C2 | 150.6 (3) | O6—S2—C12—C17 | 134.0 (3) |
O1—S1—C1—C2 | 18.3 (3) | N2—S2—C12—C17 | −113.6 (3) |
N1—S1—C1—C2 | −95.9 (3) | O5—S2—C12—C13 | −177.0 (3) |
C6—C1—C2—C3 | −0.2 (6) | O6—S2—C12—C13 | −45.4 (3) |
S1—C1—C2—C3 | 176.7 (3) | N2—S2—C12—C13 | 67.0 (3) |
C1—C2—C3—C4 | 0.5 (6) | C17—C12—C13—C14 | 2.7 (7) |
C2—C3—C4—C5 | −0.7 (7) | S2—C12—C13—C14 | −177.9 (4) |
C3—C4—C5—C6 | 0.5 (7) | C12—C13—C14—C15 | −1.6 (8) |
C2—C1—C6—C5 | 0.0 (6) | C13—C14—C15—C16 | 0.3 (10) |
S1—C1—C6—C5 | −176.9 (3) | C14—C15—C16—C17 | 0.0 (10) |
C4—C5—C6—C1 | −0.2 (7) | C13—C12—C17—C16 | −2.5 (6) |
S1—N1—C7—C8 | −84.3 (3) | S2—C12—C17—C16 | 178.1 (4) |
S1—N1—C7—C9A | 145.6 (3) | C15—C16—C17—C12 | 1.1 (8) |
S1—N1—C7—C9B | 164.6 (6) | S2—N2—C18—C19 | −93.4 (2) |
N1—C7—C8—O3 | −35.6 (5) | S2—N2—C18—C20 | 143.0 (2) |
C9A—C7—C8—O3 | 97.1 (5) | N2—C18—C19—O7 | 138.6 (3) |
C9B—C7—C8—O3 | 65.4 (8) | C20—C18—C19—O7 | −98.4 (3) |
N1—C7—C8—O4 | 144.1 (3) | N2—C18—C19—O8 | −41.7 (4) |
C9A—C7—C8—O4 | −83.3 (4) | C20—C18—C19—O8 | 81.3 (3) |
C9B—C7—C8—O4 | −114.9 (7) | N2—C18—C20—C22 | 176.9 (3) |
N1—C7—C9A—C10A | −55.9 (7) | C19—C18—C20—C22 | 53.2 (4) |
C8—C7—C9A—C10A | 173.9 (5) | N2—C18—C20—C21 | −59.7 (3) |
C9B—C7—C9A—C10A | −96.6 (14) | C19—C18—C20—C21 | 176.6 (3) |
N1—C7—C9A—C11A | 63.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8O···O3 | 0.85 (1) | 1.81 (1) | 2.649 (3) | 171 (6) |
O4—H4O···O7 | 0.86 (1) | 1.83 (2) | 2.668 (3) | 166 (6) |
N1—H1N···O1i | 0.81 (5) | 2.52 (5) | 3.322 (3) | 172 (5) |
N2—H2N···O7i | 0.82 (5) | 2.47 (5) | 3.240 (3) | 157 (5) |
N2—H2N···O8 | 0.82 (5) | 2.45 (5) | 2.734 (3) | 102 (4) |
C2—H2···O3ii | 0.93 | 2.56 | 3.440 (4) | 158 |
C4—H4···O6iii | 0.93 | 2.54 | 3.427 (4) | 161 |
C14—H14···O2iv | 0.93 | 2.52 | 3.378 (5) | 154 |
C15—H15···O1v | 0.93 | 2.60 | 3.521 (5) | 173 |
C9A—H9A···O2v | 0.98 | 2.52 | 3.421 (7) | 153 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+1; (iv) −x+1, y+1/2, −z+2; (v) −x, y+1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C11H15NO4S |
Mr | 257.30 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 5.4954 (3), 15.5097 (10), 15.5106 (9) |
β (°) | 94.043 (3) |
V (Å3) | 1318.71 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.37 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.914, 0.957 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9573, 4203, 3803 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.093, 1.05 |
No. of reflections | 4203 |
No. of parameters | 335 |
No. of restraints | 7 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.18 |
Absolute structure | Flack (1983), 1785 Friedel pairs |
Absolute structure parameter | 0.00 (6) |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), WinGX (Farrugia, 1999) and X-SEED (Barbour, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8O···O3 | 0.849 (10) | 1.806 (14) | 2.649 (3) | 171 (6) |
O4—H4O···O7 | 0.859 (10) | 1.826 (18) | 2.668 (3) | 166 (6) |
N1—H1N···O1i | 0.81 (5) | 2.52 (5) | 3.322 (3) | 172 (5) |
N2—H2N···O7i | 0.82 (5) | 2.47 (5) | 3.240 (3) | 157 (5) |
N2—H2N···O8 | 0.82 (5) | 2.45 (5) | 2.734 (3) | 102 (4) |
C2—H2···O3ii | 0.93 | 2.56 | 3.440 (4) | 158 |
C4—H4···O6iii | 0.93 | 2.54 | 3.427 (4) | 161 |
C14—H14···O2iv | 0.93 | 2.52 | 3.378 (5) | 154 |
C15—H15···O1v | 0.93 | 2.60 | 3.521 (5) | 173 |
C9A—H9A···O2v | 0.98 | 2.52 | 3.421 (7) | 153 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+1; (iv) −x+1, y+1/2, −z+2; (v) −x, y+1/2, −z+2. |
Acknowledgements
The authors acknowledge the University of Sargodha for providing diffraction facilities at its Department of Physics.
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.
Crystal structure of sulfonamide derived from lysine has been reported which proved as a new class of inhibitors, to combat the resistant variants of HIV protease (Nalam et al., 2007). Herein, we report the crystal structure of sulfonamide derived from L-valine, in countinuation of our work for the synthesis of sulfonamide (Khan et al., 2011), (Arshad et al., 2012).
The unit cell comprises of two independent molecules (C1—C11) A & (C12—C22) B. Each molecule adopted U shaped and aromatic rings are oriented with carboxylic groups at dihedral angles of 20.91 (2)° & 28.27 (2)° in molecule A and B respectively. These two molecules have been joined to each other through complex intermolecular hydrogen bonding interactions. Molecule B also undergoes intramolecular hydrogen bonding to form five membered (N2/C18/C19/O8/H2N) ring motif S11(5) (Bernstein et al., 1995). Molecules undergo typical dimerization to produce eight membered ring motifs R22(8) (Bernstein et al., 1995) through the carboxylic functional groups. This ring motif (O3/C8/O4/H4O/O7/C19/O8/H8O) lies between the two aromatic rings just like sandwich and the centroid distances of plane generated from it are 3.934 Å & 4.155 Å with aromatic rings (C1—C6) & (C12—C17) respectively. These dimers further connected through the N—H···O, O—H···O and C—H···O type interaction to form three dimensional network (Table. 1, Fig. 2). The C- atoms of isopropyl group in molecule A is disordered over two positions with occupancies ratio of 3:1.