organic compounds
(2Z)-2-{[N-(2-Formylphenyl)-4-methylbenzenesulfonamido]methyl}-3-(4-methylphenyl)prop-2-enenitrile
aDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India, bDepartment of Physics, Ranipettai Engineering College, Thenkadappathangal, Walaja 632 513, India, and cDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
*Correspondence e-mail: smurugavel27@gmail.com
In the title compound, C25H22N2O3S, the sulfonyl-bound benzene ring forms dihedral angles of 36.8 (2) and 81.4 (2)°, respectively, with the formylbenzene and methylbenzene rings. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(5) ring motif. The crystal packing is stabilized by C—H⋯O hydrogen bonds, which generate C(11) chains along the b axis. The crystal packing is further stabilized by π–π interactions [centroid–centroid distance = 3.927 (2) Å].
Related literature
For background to the pharmacological uses of ); Mandell & Sande (1992). For related structures, see: Madhanraj et al. (2012); Aziz-ur-Rehman et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).
see: Korolkovas (1988Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia (1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812010628/tk5066sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812010628/tk5066Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812010628/tk5066Isup3.cml
A solution of N-(formylphenyl)(4-methylbenzene)sulfonamide (1 mmol, 0.275 g) and potassium carbonate (1.5 mmol, 0.207 g) in acetonitrile was stirred for 15 minutes at room temperature. To this solution, (E)-2-(bromomethyl)-3-(4-methylphenyl)prop-2-enenitrile (1.2 mmol, 0.283 g) was added drop wise until the addition was completed. After the completion of the reaction, as indicated by TLC, acetonitrile was evaporated off. Ethylacetate (15 ml) and water (15 ml) were added to the crude mass. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product, which was purified through a pad of silica gel (100–200 mesh) using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colourless solid (0.41 g, 95% yield). Recrystallization was carried out using ethylacetate as solvent.
H atoms were positioned geometrically, with C—H = 0.93–0.98 Å and constrained to ride on their parent atom with Uiso(H)=1.5Ueq for methyl H atoms and 1.2Ueq(C) for other H atoms.
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 view of this biological importance, the
of the title compound (I) has been determined and the results are presented here.Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The S1 atom shows a distorted tetrahedral geometry, with the O2—S1—O3 [119.9 (1)°] and N1—S1—C8[107.5 (1)°] angles deviating from ideal tetrahedral values. The sum of bond angles around N1 (351.9°) indicates that N1 has sp2
The sulfonyl bound benzene (C8–C13) ring forms dihedral angles of 36.8 (2) and 81.4 (2)°, respectively, with the formyl benzene (C1–C6) and methylbenzene (C18—C23) rings. The dihedral angle between formyl benzene and methylbenzene rings is 87.4 (1)°. The carbonitrile side chain (C16–C24–N2) is almost linear, with the angle around the C24 atom being 177.1 (3)°. The geometric parameters of the title molecule agrees well with those reported for similar structures (Madhanraj et al., 2012, Aziz-ur-Rehman et al., 2010).The molecular structure is stabilized by a C15—H15A···O3 intramolecular hydrogen bond, forming a S(5) ring motif (Bernstein et al., 1995) (Table 1). The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. Atom C23 in the molecule at (x, y, z) donates one proton to atom O1 at (x, -1 + y, z), forming a C(11) chain along the b axis (Fig. 2). The crystal packing is further stabilized by π—π interactions with centroid—centroid distances: Cg1—Cg2iv = 3.927 (2) Å and Cg2—Cg1v = 3.927 (2) Å (Fig. 3; Cg1 and Cg2 are the centroids of C8–C13 benzene ring and C18–C23 benzene rings, respectively, symmetry code as in Fig. 3).
For background to the pharmacological uses of
see: Korolkovas (1988); Mandell & Sande (1992). For related structures, see: Madhanraj et al. (2012); Aziz-ur-Rehman et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia (1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C25H22N2O3S | F(000) = 904 |
Mr = 430.51 | Dx = 1.245 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4690 reflections |
a = 8.9432 (5) Å | θ = 2.1–26.4° |
b = 10.3004 (6) Å | µ = 0.17 mm−1 |
c = 24.9240 (15) Å | T = 293 K |
V = 2296.0 (2) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.23 × 0.17 mm |
Bruker APEXII CCD diffractometer | 4663 independent reflections |
Radiation source: fine-focus sealed tube | 3385 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 10.0 pixels mm-1 | θmax = 26.4°, θmin = 2.1° |
ω scans | h = −11→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→9 |
Tmin = 0.959, Tmax = 0.972 | l = −30→31 |
12317 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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.065P)2 + 0.0718P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
4663 reflections | Δρmax = 0.19 e Å−3 |
282 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1990 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.19 (9) |
C25H22N2O3S | V = 2296.0 (2) Å3 |
Mr = 430.51 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.9432 (5) Å | µ = 0.17 mm−1 |
b = 10.3004 (6) Å | T = 293 K |
c = 24.9240 (15) Å | 0.25 × 0.23 × 0.17 mm |
Bruker APEXII CCD diffractometer | 4663 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3385 reflections with I > 2σ(I) |
Tmin = 0.959, Tmax = 0.972 | Rint = 0.024 |
12317 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.117 | Δρmax = 0.19 e Å−3 |
S = 1.02 | Δρmin = −0.23 e Å−3 |
4663 reflections | Absolute structure: Flack (1983), 1990 Friedel pairs |
282 parameters | Absolute structure parameter: 0.19 (9) |
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 | ||
O1 | 0.3120 (4) | 0.8483 (4) | 0.6292 (2) | 0.228 (2) | |
C14 | 0.2953 (8) | 0.3803 (7) | 0.98250 (18) | 0.198 (3) | |
H14A | 0.3992 | 0.3571 | 0.9812 | 0.297* | |
H14B | 0.2363 | 0.3039 | 0.9886 | 0.297* | |
H14C | 0.2791 | 0.4411 | 1.0111 | 0.297* | |
S1 | 0.12098 (6) | 0.62642 (6) | 0.77099 (3) | 0.0654 (2) | |
C16 | 0.1285 (2) | 0.3775 (2) | 0.65770 (8) | 0.0549 (5) | |
O3 | −0.03436 (17) | 0.60536 (19) | 0.76309 (8) | 0.0833 (5) | |
C17 | 0.1732 (3) | 0.2664 (2) | 0.63569 (9) | 0.0576 (6) | |
H17 | 0.2346 | 0.2163 | 0.6576 | 0.069* | |
O2 | 0.1799 (2) | 0.75371 (16) | 0.76813 (9) | 0.0884 (6) | |
N1 | 0.20652 (19) | 0.54286 (17) | 0.72366 (8) | 0.0561 (5) | |
C24 | 0.0421 (3) | 0.4723 (3) | 0.62915 (11) | 0.0734 (7) | |
C2 | 0.4743 (3) | 0.4998 (2) | 0.73721 (10) | 0.0672 (7) | |
H2 | 0.4505 | 0.4303 | 0.7594 | 0.081* | |
C1 | 0.3624 (2) | 0.5716 (2) | 0.71374 (8) | 0.0504 (5) | |
C3 | 0.6222 (3) | 0.5311 (3) | 0.72779 (13) | 0.0800 (8) | |
H3 | 0.6976 | 0.4824 | 0.7438 | 0.096* | |
C6 | 0.3987 (3) | 0.6749 (2) | 0.68055 (10) | 0.0597 (6) | |
C18 | 0.1425 (3) | 0.2092 (2) | 0.58296 (9) | 0.0595 (6) | |
C4 | 0.6589 (3) | 0.6330 (3) | 0.69519 (11) | 0.0744 (7) | |
H4 | 0.7587 | 0.6534 | 0.6889 | 0.089* | |
C15 | 0.1553 (3) | 0.4077 (2) | 0.71546 (9) | 0.0628 (6) | |
H15A | 0.0636 | 0.3940 | 0.7354 | 0.075* | |
H15B | 0.2301 | 0.3486 | 0.7295 | 0.075* | |
C23 | 0.2278 (3) | 0.1035 (3) | 0.56710 (12) | 0.0763 (7) | |
H23 | 0.3009 | 0.0713 | 0.5901 | 0.092* | |
C5 | 0.5495 (3) | 0.7035 (3) | 0.67231 (10) | 0.0683 (7) | |
H5 | 0.5751 | 0.7732 | 0.6504 | 0.082* | |
C20 | 0.0073 (5) | 0.1869 (3) | 0.50109 (13) | 0.1054 (11) | |
H20 | −0.0705 | 0.2145 | 0.4791 | 0.126* | |
N2 | −0.0240 (4) | 0.5520 (3) | 0.60771 (12) | 0.1084 (9) | |
C8 | 0.1702 (3) | 0.5580 (3) | 0.83244 (10) | 0.0652 (7) | |
C10 | 0.1288 (5) | 0.4016 (4) | 0.90171 (14) | 0.1050 (10) | |
H10 | 0.0720 | 0.3334 | 0.9152 | 0.126* | |
C13 | 0.2949 (3) | 0.6014 (4) | 0.85973 (15) | 0.1027 (11) | |
H13 | 0.3527 | 0.6688 | 0.8461 | 0.123* | |
C22 | 0.2061 (4) | 0.0452 (3) | 0.51797 (14) | 0.0961 (10) | |
H22 | 0.2673 | −0.0235 | 0.5077 | 0.115* | |
C19 | 0.0291 (4) | 0.2479 (3) | 0.54918 (12) | 0.0904 (9) | |
H19 | −0.0332 | 0.3160 | 0.5592 | 0.109* | |
C25 | 0.0719 (6) | 0.0218 (5) | 0.43028 (15) | 0.1551 (19) | |
H25A | 0.0117 | 0.0767 | 0.4079 | 0.233* | |
H25B | 0.0219 | −0.0597 | 0.4355 | 0.233* | |
H25C | 0.1668 | 0.0071 | 0.4133 | 0.233* | |
C7 | 0.2845 (4) | 0.7516 (3) | 0.65304 (15) | 0.1055 (12) | |
H7 | 0.1859 | 0.7232 | 0.6543 | 0.127* | |
C21 | 0.0960 (5) | 0.0869 (3) | 0.48418 (12) | 0.0964 (10) | |
C9 | 0.0865 (3) | 0.4586 (3) | 0.85373 (12) | 0.0816 (8) | |
H9 | 0.0014 | 0.4297 | 0.8359 | 0.098* | |
C11 | 0.2499 (5) | 0.4419 (5) | 0.92945 (15) | 0.1210 (14) | |
C12 | 0.3324 (4) | 0.5417 (6) | 0.90856 (18) | 0.1314 (17) | |
H12 | 0.4158 | 0.5709 | 0.9273 | 0.158* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.130 (2) | 0.192 (3) | 0.363 (5) | −0.020 (2) | −0.038 (3) | 0.212 (4) |
C14 | 0.248 (7) | 0.247 (6) | 0.100 (3) | 0.073 (6) | −0.044 (4) | 0.005 (4) |
S1 | 0.0426 (3) | 0.0560 (3) | 0.0975 (5) | 0.0013 (3) | 0.0086 (3) | −0.0120 (3) |
C16 | 0.0484 (11) | 0.0527 (12) | 0.0636 (13) | −0.0027 (12) | 0.0040 (11) | 0.0009 (11) |
O3 | 0.0409 (9) | 0.0969 (13) | 0.1122 (14) | 0.0073 (9) | −0.0007 (9) | −0.0069 (12) |
C17 | 0.0535 (13) | 0.0545 (14) | 0.0647 (14) | −0.0001 (11) | 0.0035 (10) | 0.0060 (12) |
O2 | 0.0722 (11) | 0.0487 (9) | 0.1445 (16) | 0.0002 (8) | 0.0266 (11) | −0.0155 (12) |
N1 | 0.0475 (10) | 0.0491 (10) | 0.0718 (12) | −0.0060 (8) | 0.0032 (9) | −0.0044 (10) |
C24 | 0.0756 (17) | 0.0689 (18) | 0.0757 (16) | 0.0102 (15) | 0.0020 (14) | −0.0112 (15) |
C2 | 0.0635 (15) | 0.0590 (14) | 0.0792 (16) | 0.0129 (11) | −0.0054 (13) | 0.0094 (13) |
C1 | 0.0453 (11) | 0.0465 (11) | 0.0595 (12) | 0.0036 (9) | 0.0008 (10) | −0.0049 (10) |
C3 | 0.0534 (14) | 0.0804 (17) | 0.106 (2) | 0.0212 (14) | −0.0092 (16) | −0.0056 (17) |
C6 | 0.0544 (14) | 0.0539 (13) | 0.0707 (15) | −0.0020 (10) | −0.0005 (12) | 0.0046 (12) |
C18 | 0.0648 (15) | 0.0526 (14) | 0.0611 (14) | 0.0018 (12) | 0.0069 (12) | 0.0049 (11) |
C4 | 0.0455 (14) | 0.0896 (19) | 0.0881 (18) | −0.0005 (14) | 0.0097 (13) | −0.0230 (17) |
C15 | 0.0679 (15) | 0.0540 (13) | 0.0666 (14) | −0.0154 (11) | 0.0049 (12) | −0.0052 (12) |
C23 | 0.0712 (17) | 0.0681 (17) | 0.0895 (19) | 0.0102 (14) | −0.0001 (14) | −0.0087 (16) |
C5 | 0.0649 (17) | 0.0665 (16) | 0.0736 (16) | −0.0135 (13) | 0.0092 (13) | −0.0028 (13) |
C20 | 0.141 (3) | 0.091 (2) | 0.085 (2) | 0.021 (2) | −0.032 (2) | −0.0105 (19) |
N2 | 0.127 (2) | 0.0856 (18) | 0.112 (2) | 0.0383 (18) | −0.0249 (18) | −0.0046 (16) |
C8 | 0.0452 (12) | 0.0717 (17) | 0.0787 (16) | 0.0009 (12) | 0.0043 (11) | −0.0293 (14) |
C10 | 0.134 (3) | 0.097 (3) | 0.084 (2) | −0.001 (3) | 0.008 (2) | −0.0085 (19) |
C13 | 0.0679 (18) | 0.142 (3) | 0.098 (2) | −0.026 (2) | 0.0056 (17) | −0.043 (2) |
C22 | 0.108 (2) | 0.082 (2) | 0.099 (2) | 0.0099 (19) | 0.018 (2) | −0.0267 (19) |
C19 | 0.110 (2) | 0.0745 (19) | 0.086 (2) | 0.0275 (18) | −0.0280 (17) | −0.0168 (16) |
C25 | 0.223 (5) | 0.151 (4) | 0.092 (2) | −0.003 (4) | −0.014 (3) | −0.053 (3) |
C7 | 0.082 (2) | 0.084 (2) | 0.150 (3) | −0.0029 (17) | −0.018 (2) | 0.056 (2) |
C21 | 0.132 (3) | 0.086 (2) | 0.0709 (18) | −0.006 (2) | 0.005 (2) | −0.0170 (17) |
C9 | 0.079 (2) | 0.084 (2) | 0.0825 (19) | −0.0122 (16) | 0.0012 (14) | −0.0170 (17) |
C11 | 0.119 (3) | 0.159 (4) | 0.085 (3) | 0.027 (3) | −0.001 (2) | −0.029 (3) |
C12 | 0.085 (3) | 0.216 (5) | 0.093 (3) | −0.002 (3) | −0.021 (2) | −0.056 (3) |
O1—C7 | 1.185 (4) | C4—H4 | 0.9300 |
C14—C11 | 1.522 (6) | C15—H15A | 0.9700 |
C14—H14A | 0.9600 | C15—H15B | 0.9700 |
C14—H14B | 0.9600 | C23—C22 | 1.378 (4) |
C14—H14C | 0.9600 | C23—H23 | 0.9300 |
S1—O2 | 1.4148 (18) | C5—H5 | 0.9300 |
S1—O3 | 1.4198 (17) | C20—C21 | 1.367 (5) |
S1—N1 | 1.649 (2) | C20—C19 | 1.367 (4) |
S1—C8 | 1.742 (3) | C20—H20 | 0.9300 |
C16—C17 | 1.331 (3) | C8—C9 | 1.375 (4) |
C16—C24 | 1.434 (4) | C8—C13 | 1.381 (4) |
C16—C15 | 1.492 (3) | C10—C11 | 1.351 (5) |
C17—C18 | 1.466 (3) | C10—C9 | 1.385 (5) |
C17—H17 | 0.9300 | C10—H10 | 0.9300 |
N1—C1 | 1.447 (3) | C13—C12 | 1.404 (6) |
N1—C15 | 1.479 (3) | C13—H13 | 0.9300 |
C24—N2 | 1.145 (3) | C22—C21 | 1.365 (5) |
C2—C1 | 1.375 (3) | C22—H22 | 0.9300 |
C2—C3 | 1.381 (4) | C19—H19 | 0.9300 |
C2—H2 | 0.9300 | C25—C21 | 1.517 (5) |
C1—C6 | 1.386 (3) | C25—H25A | 0.9600 |
C3—C4 | 1.367 (4) | C25—H25B | 0.9600 |
C3—H3 | 0.9300 | C25—H25C | 0.9600 |
C6—C5 | 1.396 (4) | C7—H7 | 0.9300 |
C6—C7 | 1.462 (4) | C9—H9 | 0.9300 |
C18—C19 | 1.377 (4) | C11—C12 | 1.368 (6) |
C18—C23 | 1.388 (3) | C12—H12 | 0.9300 |
C4—C5 | 1.345 (4) | ||
C11—C14—H14A | 109.5 | C22—C23—C18 | 121.2 (3) |
C11—C14—H14B | 109.5 | C22—C23—H23 | 119.4 |
H14A—C14—H14B | 109.5 | C18—C23—H23 | 119.4 |
C11—C14—H14C | 109.5 | C4—C5—C6 | 121.7 (3) |
H14A—C14—H14C | 109.5 | C4—C5—H5 | 119.1 |
H14B—C14—H14C | 109.5 | C6—C5—H5 | 119.1 |
O2—S1—O3 | 119.94 (12) | C21—C20—C19 | 122.3 (3) |
O2—S1—N1 | 105.95 (11) | C21—C20—H20 | 118.9 |
O3—S1—N1 | 105.96 (11) | C19—C20—H20 | 118.9 |
O2—S1—C8 | 108.98 (13) | C9—C8—C13 | 119.4 (3) |
O3—S1—C8 | 107.90 (12) | C9—C8—S1 | 120.2 (2) |
N1—S1—C8 | 107.49 (10) | C13—C8—S1 | 120.4 (3) |
C17—C16—C24 | 122.9 (2) | C11—C10—C9 | 122.0 (4) |
C17—C16—C15 | 121.9 (2) | C11—C10—H10 | 119.0 |
C24—C16—C15 | 115.0 (2) | C9—C10—H10 | 119.0 |
C16—C17—C18 | 131.2 (2) | C8—C13—C12 | 118.5 (4) |
C16—C17—H17 | 114.4 | C8—C13—H13 | 120.7 |
C18—C17—H17 | 114.4 | C12—C13—H13 | 120.7 |
C1—N1—C15 | 117.84 (18) | C21—C22—C23 | 120.8 (3) |
C1—N1—S1 | 117.57 (14) | C21—C22—H22 | 119.6 |
C15—N1—S1 | 116.52 (15) | C23—C22—H22 | 119.6 |
N2—C24—C16 | 177.1 (3) | C20—C19—C18 | 120.5 (3) |
C1—C2—C3 | 119.9 (2) | C20—C19—H19 | 119.7 |
C1—C2—H2 | 120.0 | C18—C19—H19 | 119.7 |
C3—C2—H2 | 120.0 | C21—C25—H25A | 109.5 |
C2—C1—C6 | 119.7 (2) | C21—C25—H25B | 109.5 |
C2—C1—N1 | 121.3 (2) | H25A—C25—H25B | 109.5 |
C6—C1—N1 | 118.99 (19) | C21—C25—H25C | 109.5 |
C4—C3—C2 | 120.7 (2) | H25A—C25—H25C | 109.5 |
C4—C3—H3 | 119.7 | H25B—C25—H25C | 109.5 |
C2—C3—H3 | 119.7 | O1—C7—C6 | 123.0 (3) |
C1—C6—C5 | 118.4 (2) | O1—C7—H7 | 118.5 |
C1—C6—C7 | 122.1 (2) | C6—C7—H7 | 118.5 |
C5—C6—C7 | 119.5 (3) | C22—C21—C20 | 117.8 (3) |
C19—C18—C23 | 117.2 (2) | C22—C21—C25 | 120.6 (4) |
C19—C18—C17 | 124.8 (2) | C20—C21—C25 | 121.6 (4) |
C23—C18—C17 | 117.9 (2) | C8—C9—C10 | 120.0 (3) |
C5—C4—C3 | 119.5 (2) | C8—C9—H9 | 120.0 |
C5—C4—H4 | 120.3 | C10—C9—H9 | 120.0 |
C3—C4—H4 | 120.3 | C10—C11—C12 | 118.0 (4) |
N1—C15—C16 | 112.3 (2) | C10—C11—C14 | 122.0 (5) |
N1—C15—H15A | 109.1 | C12—C11—C14 | 120.0 (5) |
C16—C15—H15A | 109.1 | C11—C12—C13 | 122.0 (4) |
N1—C15—H15B | 109.1 | C11—C12—H12 | 119.0 |
C16—C15—H15B | 109.1 | C13—C12—H12 | 119.0 |
H15A—C15—H15B | 107.9 | ||
C24—C16—C17—C18 | −4.5 (4) | C3—C4—C5—C6 | −0.6 (4) |
C15—C16—C17—C18 | 170.8 (2) | C1—C6—C5—C4 | 0.7 (4) |
O2—S1—N1—C1 | 36.60 (19) | C7—C6—C5—C4 | −177.6 (3) |
O3—S1—N1—C1 | 165.03 (17) | O2—S1—C8—C9 | 156.4 (2) |
C8—S1—N1—C1 | −79.81 (18) | O3—S1—C8—C9 | 24.6 (2) |
O2—S1—N1—C15 | −175.28 (18) | N1—S1—C8—C9 | −89.2 (2) |
O3—S1—N1—C15 | −46.8 (2) | O2—S1—C8—C13 | −24.7 (3) |
C8—S1—N1—C15 | 68.32 (19) | O3—S1—C8—C13 | −156.5 (2) |
C17—C16—C24—N2 | −151 (6) | N1—S1—C8—C13 | 89.7 (2) |
C15—C16—C24—N2 | 33 (7) | C9—C8—C13—C12 | 0.3 (5) |
C3—C2—C1—C6 | 0.2 (4) | S1—C8—C13—C12 | −178.7 (3) |
C3—C2—C1—N1 | −178.8 (2) | C18—C23—C22—C21 | −2.5 (5) |
C15—N1—C1—C2 | −52.1 (3) | C21—C20—C19—C18 | −0.5 (6) |
S1—N1—C1—C2 | 95.6 (2) | C23—C18—C19—C20 | −2.7 (5) |
C15—N1—C1—C6 | 128.9 (2) | C17—C18—C19—C20 | −178.7 (3) |
S1—N1—C1—C6 | −83.4 (2) | C1—C6—C7—O1 | 171.7 (4) |
C1—C2—C3—C4 | −0.1 (4) | C5—C6—C7—O1 | −10.1 (6) |
C2—C1—C6—C5 | −0.5 (3) | C23—C22—C21—C20 | −0.8 (5) |
N1—C1—C6—C5 | 178.5 (2) | C23—C22—C21—C25 | −179.6 (4) |
C2—C1—C6—C7 | 177.8 (3) | C19—C20—C21—C22 | 2.3 (6) |
N1—C1—C6—C7 | −3.3 (4) | C19—C20—C21—C25 | −179.0 (4) |
C16—C17—C18—C19 | −16.3 (4) | C13—C8—C9—C10 | −1.0 (4) |
C16—C17—C18—C23 | 167.7 (2) | S1—C8—C9—C10 | 177.9 (2) |
C2—C3—C4—C5 | 0.3 (4) | C11—C10—C9—C8 | 1.2 (5) |
C1—N1—C15—C16 | −79.8 (3) | C9—C10—C11—C12 | −0.5 (6) |
S1—N1—C15—C16 | 132.11 (18) | C9—C10—C11—C14 | 179.3 (4) |
C17—C16—C15—N1 | 136.8 (2) | C10—C11—C12—C13 | −0.3 (6) |
C24—C16—C15—N1 | −47.5 (3) | C14—C11—C12—C13 | 179.9 (4) |
C19—C18—C23—C22 | 4.2 (4) | C8—C13—C12—C11 | 0.4 (6) |
C17—C18—C23—C22 | −179.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···O3 | 0.97 | 2.45 | 2.904 (3) | 109 |
C23—H23···O1i | 0.93 | 2.50 | 3.142 (4) | 127 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C25H22N2O3S |
Mr | 430.51 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 8.9432 (5), 10.3004 (6), 24.9240 (15) |
V (Å3) | 2296.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.17 |
Crystal size (mm) | 0.25 × 0.23 × 0.17 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.959, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12317, 4663, 3385 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.117, 1.02 |
No. of reflections | 4663 |
No. of parameters | 282 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.23 |
Absolute structure | Flack (1983), 1990 Friedel pairs |
Absolute structure parameter | 0.19 (9) |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia (1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···O3 | 0.97 | 2.45 | 2.904 (3) | 109 |
C23—H23···O1i | 0.93 | 2.50 | 3.142 (4) | 127 |
Symmetry code: (i) x, y−1, z. |
Footnotes
‡Additional correspondence author, e-mail: bhakthadoss@yahoo.com.
Acknowledgements
The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.
References
Aziz-ur-Rehman, Tanveer, W., Akkurt, M., Sattar, A., Abbasi, M. A. & Khan, I. U. (2010). Acta Cryst. E66, o2980. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Korolkovas, A. (1988). Essentials of Medicinal Chemistry, 2nd ed., pp. 699–716. New York: Wiley. Google Scholar
Madhanraj, R., Murugavel, S., Kannan, D. & Bakthadoss, M. (2012). Acta Cryst. E68, o56–o57. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mandell, G. L. & Sande, M. A. (1992). In Goodman and Gilman, The Pharmacological Basis of Therapeutics 2, edited by A. Gilman, T. W. Rall, A. S. Nies & P. Taylor, 8th ed., pp. 1047–1057. Singapore: McGraw–Hill. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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 view of this biological importance, the crystal structure of the title compound (I) has been determined and the results are presented here.
Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The S1 atom shows a distorted tetrahedral geometry, with the O2—S1—O3 [119.9 (1)°] and N1—S1—C8[107.5 (1)°] angles deviating from ideal tetrahedral values. The sum of bond angles around N1 (351.9°) indicates that N1 has sp2 hybridization. The sulfonyl bound benzene (C8–C13) ring forms dihedral angles of 36.8 (2) and 81.4 (2)°, respectively, with the formyl benzene (C1–C6) and methylbenzene (C18—C23) rings. The dihedral angle between formyl benzene and methylbenzene rings is 87.4 (1)°. The carbonitrile side chain (C16–C24–N2) is almost linear, with the angle around the C24 atom being 177.1 (3)°. The geometric parameters of the title molecule agrees well with those reported for similar structures (Madhanraj et al., 2012, Aziz-ur-Rehman et al., 2010).
The molecular structure is stabilized by a C15—H15A···O3 intramolecular hydrogen bond, forming a S(5) ring motif (Bernstein et al., 1995) (Table 1). The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. Atom C23 in the molecule at (x, y, z) donates one proton to atom O1 at (x, -1 + y, z), forming a C(11) chain along the b axis (Fig. 2). The crystal packing is further stabilized by π—π interactions with centroid—centroid distances: Cg1—Cg2iv = 3.927 (2) Å and Cg2—Cg1v = 3.927 (2) Å (Fig. 3; Cg1 and Cg2 are the centroids of C8–C13 benzene ring and C18–C23 benzene rings, respectively, symmetry code as in Fig. 3).