(E)-3-(1,3-Benzodioxol-5-yl)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfon­amido]methyl}prop-2-enenitrile

Bakthadoss, M.; Devaraj, A.; Madhanraj, R.; Murugavel, S.

doi:10.1107/S1600536812042663

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3164-o3165

doi:10.1107/S1600536812042663

Open

access

(E)-3-(1,3-Benzodioxol-5-yl)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfonamido]methyl}prop-2-enenitrile

M. Bakthadoss,^a,^b ‡ A. Devaraj,^a R. Madhanraj ^c and S. Murugavel ^d ^*

^aDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India, ^bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India, ^cDepartment of Physics, Ganadipathy Tulsi's Jain Engineering College, Kaniyambadi, Vellore 632 102, India, and ^dDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
^*Correspondence e-mail: smurugavel27@gmail.com

(Received 1 October 2012; accepted 11 October 2012; online 20 October 2012)

In the title compound, C₂₅H₂₀N₂O₅S, the benzodioxole ring system is essentially planar [maximum deviation = 0.021 (2) Å] and forms dihedral angles of 85.2 (1) and 74.2 (1)°, respectively, with the formyl benzene and sulfonyl-bound benzene rings. In the crystal, C—H⋯O hydrogen bonds generate C(8) chains along [100] and R₃³(19) ring motifs. In addition, a weak π–π interaction [centroid–centroid distance = 3.937 (3) Å] is also observed.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ); Mandell & Sande (1992 ). For benzodioxole derivatives, see: Ullrich et al. (2004 ); Gates & Gillon (1974 ); Arndt & Franke (1977 ); Joshi et al. (2005 ); Jae et al. (2001 ); Leite et al. (2004 ). For related structures, see: Madhanraj et al. (2011 ); Aziz-ur-Rehman et al. (2010 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the Thrope–Ingold effect, see: Bassindale (1984 ).

Experimental

Crystal data

C₂₅H₂₀N₂O₅S
M_r = 460.49
Monoclinic, P 2₁ /n
a = 8.921 (5) Å
b = 10.235 (4) Å
c = 25.256 (3) Å
β = 93.380 (4)°
V = 2302.0 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 293 K
0.23 × 0.21 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.959, T_max = 0.972
26810 measured reflections
6451 independent reflections
3582 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.148
S = 1.01
6451 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O2ⁱ	0.97	2.42	3.282 (3)	148
C23—H23⋯O1ⁱⁱ	0.93	2.41	3.114 (3)	132
C4—H4⋯O3ⁱⁱⁱ	0.93	2.59	3.195 (3)	124
Symmetry codes: (i) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y-1, z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812042663/bt6843sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042663/bt6843Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042663/bt6843Isup3.cml

checkCIF report

Comment top

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). Benzodioxoles derivatives can be used as inhibitors of mono-oxygenase enzymes (Ullrich et al., 2004), pesticides or pesticide intermediates (Gates & Gillon, 1974), herbicides (Arndt & Franke, 1977), antioxidants (Joshi et al., 2005), antimicrobials (Jae et al., 2001) and medicines (Leite et al., 2004). In view of this biological importance, the crystal structure of the title compound has been determined and the results are presented here.

Fig. 1. shows a displacement ellipsoid plot of the title compound, with the atom numbering scheme. The S1 atom shows a distorted tetrahedral geometry, with O2—S1—O3[119.9 (1)°] and N1—S1—C8[107.0 (1)°] angles deviating from ideal tetrahedral values, are attributed to the Thrope-Ingold effect (Bassindale, 1984). The sum of bond angles around N1 (351°) indicates that N1 is in sp² hybridization. The benzodioxole ring system is essentially planar [maximum deviation = 0.021 (2) Å for the O5 atom] and forms dihedral angles of 85.2 (1)° and 74.2 (1)°, respectively, with the formyl benzene and sulfonyl–bound benzene rings. The carbonitrile side chain (C16–C24–N2) is almost linear, with the angle around central carbon atom being 177.1 (2)°. The geometric parameters of the title molecule agree well with those reported for similar structures (Madhanraj et al., 2011; Aziz-ur-Rehman et al., 2010).

The molecular structure is stabilized by an C15—H15B···O3 intramolecular hydrogen bond, forming an S(5) ring motif (Bernstein et al., 1995) (Table 1). The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. The formation of the framework can be explained in terms of two-one substructures. In the first substructure, atom C4 in the molecule at (x, y, z) acts as a hydrogen bond donor to atom O3 in the molecule at (-1+x, y, z) generating C(8) chains which are running along [100] (Fig. 2). In the second substructure, three molecules are linked by the combination of C15—H15B···O2 and C23—H23···O1 intermolecular hydrogen bonds generating R₃³(19) ring motifs along [010] (Fig. 3). The crystal packing (Fig. 4) is further stabilized by weak C—H···π interactions between a dioxole H atom and the benzene ring (C1–C6) of a neighbouring molecule, with a C25—H25A···Cg1^iv distance of 3.446 (4) Å (Table 1; Cg1 is the centroid of the C1–C6 benzene ring, Symmetry code: iv = 2-x, -y, 1-z). Additional stability arises from weak aromatic π—π interaction between the benzene rings of neighbouring molecules, with Cg2—Cg2^iv distance of 3.937 (3) Å (Fig. 4; Cg2 is the centroid of the C18—C23 benzene ring, symmetry code: iv = 2-x, -y, 1-z).

Related literature top

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988); Mandell & Sande (1992). For benzodioxole derivatives, see: Ullrich et al. (2004); Gates & Gillon (1974); Arndt & Franke (1977); Joshi et al. (2005); Jae et al. (2001); Leite et al. (2004). For related structures, see: Madhanraj et al. (2011); Aziz-ur-Rehman et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the Thrope–Ingold effect, see: Bassindale (1984).

Experimental top

To a stirred solution of N-(2-formylphenyl)-4-methylbenzenesulfonamide (0.275 g, 1 mmol) in acetonitrile (7 ml), potassium carbonate (0.35 g, 2.5 mmol) was added and stirred well for five minutes. To this solution, (z)-methyl 3-(benzo[d][1,3]dioxol-5-yl)-2- (bromomethyl)prop-2-enenitrile (0.299 g, 1 mmol) in acetonitrile (0.5 ml) was added and allowed to stir well for 6 h. After the completion of the reaction, the reaction mixture was poured into water and extracted using ethyl acetate. The organic layer thus obtained was concentrated under reduced pressure and the residual mass thus obtained was purified by column chromatography on silica gel (100–200 mesh) using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colourless solid (0.435 g, 94% yield). Recrystallization was carried out using ethylacetate as solvent.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: 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).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 20% probability level. H atoms are presented as a small cycles of arbitrary radius.
	Fig. 2. Part of the crystal structure of (I) showing C—H···O hydrogen bonds (dotted lines), with the formation of C(8) chains along [100]. [Symmetry codes: (iii)-1+x, y, z; (v)-2+x, y, z; (vi)-3+x, y, z].
	Fig. 3. Part of the crystal structure of (I) showing C—H···O hydrogen bonds (dotted lines), with the formation of R₃³(19) ring motifs along [010] [Symmetry codes: (i)5/2-x, -1/2+y, 3/2-z; (ii)x, -1+y, z; (vii)5/2-x, -3/2+y, 3/2-z; (viii)x, -2+y, z; (ix)5/2-x, -5/2+y, 3/2-z].
	Fig. 4. A view of the C—H···π and π—π interactions (dotted lines) in the crystal structure of the title compound. Cg1 and Cg2 denotes centroids of the C1–C6 benzene ring and C18–C23 benzene ring, respectively. [Symmetry codes: (iv)2-x,-y,1-z].

(E)-3-(1,3-Benzodioxol-5-yl)-2-{[N-(2-formylphenyl)- 4-methylbenzenesulfonamido]methyl}prop-2-enenitrile top

Crystal data top

C₂₅H₂₀N₂O₅S	F(000) = 960
M_r = 460.49	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6508 reflections
a = 8.921 (5) Å	θ = 2.2–29.6°
b = 10.235 (4) Å	µ = 0.18 mm⁻¹
c = 25.256 (3) Å	T = 293 K
β = 93.380 (4)°	Block, colourless
V = 2302.0 (16) Å³	0.23 × 0.21 × 0.16 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	6451 independent reflections
Radiation source: fine-focus sealed tube	3582 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 10.0 pixels mm^-1	θ_max = 29.6°, θ_min = 2.2°
ω scans	h = −11→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→14
T_min = 0.959, T_max = 0.972	l = −35→35
26810 measured reflections

Refinement top

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.061P)² + 0.4367P] where P = (F_o² + 2F_c²)/3
6451 reflections	(Δ/σ)_max = 0.001
299 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₅H₂₀N₂O₅S	V = 2302.0 (16) Å³
M_r = 460.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.921 (5) Å	µ = 0.18 mm⁻¹
b = 10.235 (4) Å	T = 293 K
c = 25.256 (3) Å	0.23 × 0.21 × 0.16 mm
β = 93.380 (4)°

Data collection top

Bruker APEXII CCD diffractometer	6451 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3582 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.972	R_int = 0.035
26810 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.01	Δρ_max = 0.24 e Å⁻³
6451 reflections	Δρ_min = −0.28 e Å⁻³
299 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.88821 (17)	0.29000 (16)	0.70678 (7)	0.0460 (4)
C2	0.7817 (2)	0.21821 (19)	0.73197 (8)	0.0583 (5)
H2	0.8111	0.1480	0.7535	0.070*
C3	0.6312 (2)	0.2512 (2)	0.72499 (9)	0.0708 (6)
H3	0.5597	0.2020	0.7415	0.085*
C4	0.5870 (2)	0.3551 (2)	0.69422 (9)	0.0720 (6)
H4	0.4860	0.3776	0.6903	0.086*
C5	0.6909 (2)	0.4257 (2)	0.66930 (9)	0.0690 (5)
H5	0.6600	0.4964	0.6482	0.083*
C6	0.8425 (2)	0.39395 (18)	0.67483 (8)	0.0571 (5)
C7	0.9488 (3)	0.4706 (3)	0.64478 (12)	0.0993 (9)
H7	1.0464	0.4397	0.6429	0.119*
C8	1.0796 (2)	0.2967 (2)	0.82269 (8)	0.0615 (5)
C9	1.1506 (3)	0.1941 (2)	0.84920 (10)	0.0804 (6)
H9	1.2329	0.1535	0.8353	0.096*
C10	1.0975 (4)	0.1524 (3)	0.89685 (12)	0.1011 (9)
H10	1.1449	0.0831	0.9148	0.121*
C11	0.9766 (4)	0.2113 (4)	0.91805 (12)	0.1072 (10)
C12	0.9091 (3)	0.3127 (4)	0.89092 (13)	0.1068 (9)
H12	0.8270	0.3534	0.9049	0.128*
C13	0.9580 (3)	0.3563 (2)	0.84401 (10)	0.0836 (7)
H13	0.9098	0.4257	0.8264	0.100*
C14	0.9192 (5)	0.1625 (5)	0.96973 (14)	0.1774 (19)
H14A	0.8719	0.2330	0.9874	0.266*
H14B	1.0017	0.1297	0.9920	0.266*
H14C	0.8476	0.0938	0.9625	0.266*
C15	1.0965 (2)	0.12671 (18)	0.70817 (8)	0.0607 (5)
H15A	1.0210	0.0672	0.7202	0.073*
H15B	1.1883	0.1123	0.7299	0.073*
C16	1.12431 (19)	0.09650 (18)	0.65121 (7)	0.0547 (4)
C17	1.0763 (2)	−0.01502 (18)	0.62804 (8)	0.0570 (5)
H17	1.0133	−0.0641	0.6483	0.068*
C18	1.1044 (2)	−0.07351 (18)	0.57716 (7)	0.0570 (5)
C19	1.2126 (3)	−0.0279 (2)	0.54337 (8)	0.0743 (6)
H19	1.2694	0.0464	0.5516	0.089*
C20	1.2309 (3)	−0.0963 (2)	0.49839 (9)	0.0778 (6)
C21	1.1496 (3)	−0.2059 (2)	0.48521 (9)	0.0798 (6)
C22	1.0463 (3)	−0.2538 (2)	0.51699 (10)	0.0911 (8)
H22	0.9916	−0.3288	0.5082	0.109*
C23	1.0258 (3)	−0.1855 (2)	0.56332 (9)	0.0741 (6)
H23	0.9558	−0.2165	0.5861	0.089*
C24	1.2139 (2)	0.1901 (2)	0.62545 (9)	0.0708 (6)
C25	1.3046 (4)	−0.1707 (3)	0.42145 (11)	0.1120 (10)
H25A	1.2715	−0.1314	0.3878	0.134*
H25B	1.3966	−0.2186	0.4165	0.134*
N1	1.04579 (15)	0.26209 (13)	0.71551 (6)	0.0523 (4)
N2	1.2828 (3)	0.2688 (2)	0.60623 (9)	0.1089 (8)
O1	0.9152 (3)	0.5697 (3)	0.62298 (14)	0.1952 (15)
O2	1.08789 (15)	0.48120 (13)	0.75324 (7)	0.0788 (4)
O3	1.29242 (13)	0.31885 (16)	0.75875 (7)	0.0844 (5)
O4	1.1940 (3)	−0.2561 (2)	0.43819 (7)	0.1168 (7)
O5	1.3313 (3)	−0.0722 (2)	0.46024 (7)	0.1254 (8)
S1	1.13777 (5)	0.34993 (5)	0.76162 (2)	0.06199 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0383 (8)	0.0409 (8)	0.0596 (10)	−0.0011 (7)	0.0085 (7)	−0.0013 (8)
C2	0.0554 (11)	0.0548 (11)	0.0657 (12)	−0.0087 (9)	0.0117 (9)	0.0054 (9)
C3	0.0455 (10)	0.0779 (14)	0.0907 (15)	−0.0188 (10)	0.0180 (10)	−0.0106 (12)
C4	0.0411 (10)	0.0852 (16)	0.0894 (15)	0.0038 (10)	0.0008 (10)	−0.0146 (13)
C5	0.0615 (12)	0.0646 (13)	0.0802 (14)	0.0145 (10)	−0.0026 (10)	0.0018 (11)
C6	0.0482 (10)	0.0492 (10)	0.0748 (12)	0.0024 (8)	0.0105 (9)	0.0069 (9)
C7	0.0858 (17)	0.0776 (16)	0.137 (2)	0.0021 (13)	0.0276 (16)	0.0496 (16)
C8	0.0434 (9)	0.0609 (11)	0.0794 (13)	−0.0038 (9)	−0.0038 (9)	−0.0227 (10)
C9	0.0644 (13)	0.0822 (16)	0.0931 (17)	0.0013 (12)	−0.0080 (12)	−0.0174 (14)
C10	0.107 (2)	0.105 (2)	0.0874 (19)	−0.0205 (18)	−0.0199 (17)	0.0057 (16)
C11	0.106 (2)	0.136 (3)	0.0801 (18)	−0.037 (2)	0.0101 (17)	−0.0326 (19)
C12	0.094 (2)	0.124 (2)	0.105 (2)	−0.0081 (19)	0.0311 (17)	−0.039 (2)
C13	0.0698 (14)	0.0851 (16)	0.0974 (18)	0.0046 (12)	0.0176 (13)	−0.0266 (14)
C14	0.203 (4)	0.244 (5)	0.088 (2)	−0.061 (4)	0.033 (2)	−0.002 (3)
C15	0.0602 (11)	0.0530 (10)	0.0693 (12)	0.0162 (9)	0.0083 (9)	−0.0018 (9)
C16	0.0461 (9)	0.0556 (11)	0.0625 (11)	0.0076 (8)	0.0058 (8)	0.0000 (9)
C17	0.0544 (10)	0.0524 (10)	0.0643 (11)	0.0041 (9)	0.0046 (9)	0.0066 (9)
C18	0.0611 (11)	0.0500 (10)	0.0593 (11)	0.0019 (9)	−0.0010 (9)	0.0032 (8)
C19	0.0934 (16)	0.0631 (12)	0.0672 (13)	−0.0196 (12)	0.0133 (11)	−0.0060 (10)
C20	0.1023 (17)	0.0726 (14)	0.0598 (13)	−0.0106 (13)	0.0150 (12)	−0.0013 (11)
C21	0.1077 (18)	0.0704 (14)	0.0607 (13)	−0.0056 (14)	0.0010 (12)	−0.0096 (11)
C22	0.110 (2)	0.0724 (15)	0.0909 (18)	−0.0265 (14)	0.0079 (15)	−0.0197 (13)
C23	0.0794 (14)	0.0626 (13)	0.0809 (15)	−0.0122 (11)	0.0103 (11)	−0.0005 (11)
C24	0.0687 (13)	0.0712 (13)	0.0741 (14)	−0.0141 (11)	0.0173 (11)	−0.0181 (11)
C25	0.156 (3)	0.115 (2)	0.0679 (16)	−0.012 (2)	0.0270 (17)	−0.0224 (16)
N1	0.0398 (7)	0.0451 (8)	0.0725 (10)	0.0052 (6)	0.0084 (7)	−0.0033 (7)
N2	0.1215 (18)	0.1053 (17)	0.1043 (16)	−0.0526 (15)	0.0437 (14)	−0.0253 (13)
O1	0.144 (2)	0.142 (2)	0.305 (4)	0.0164 (17)	0.054 (2)	0.157 (3)
O2	0.0565 (8)	0.0483 (8)	0.1309 (13)	−0.0080 (6)	0.0003 (8)	−0.0096 (8)
O3	0.0349 (7)	0.0990 (12)	0.1201 (13)	−0.0006 (7)	0.0105 (7)	−0.0133 (10)
O4	0.170 (2)	0.1052 (14)	0.0777 (12)	−0.0327 (14)	0.0295 (12)	−0.0314 (10)
O5	0.183 (2)	0.1159 (15)	0.0837 (12)	−0.0514 (15)	0.0614 (13)	−0.0252 (11)
S1	0.0339 (2)	0.0565 (3)	0.0959 (4)	−0.0033 (2)	0.0072 (2)	−0.0108 (3)

Geometric parameters (Å, º) top

C1—C6	1.382 (2)	C14—H14C	0.9600
C1—C2	1.385 (2)	C15—N1	1.473 (2)
C1—N1	1.439 (2)	C15—C16	1.506 (3)
C2—C3	1.386 (3)	C15—H15A	0.9700
C2—H2	0.9300	C15—H15B	0.9700
C3—C4	1.361 (3)	C16—C17	1.341 (3)
C3—H3	0.9300	C16—C24	1.429 (3)
C4—C5	1.359 (3)	C17—C18	1.453 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.390 (3)	C18—C23	1.378 (3)
C5—H5	0.9300	C18—C19	1.406 (3)
C6—C7	1.475 (3)	C19—C20	1.352 (3)
C7—O1	1.184 (3)	C19—H19	0.9300
C7—H7	0.9300	C20—C21	1.367 (3)
C8—C9	1.379 (3)	C20—O5	1.376 (3)
C8—C13	1.381 (3)	C21—C22	1.349 (3)
C8—S1	1.743 (2)	C21—O4	1.373 (3)
C9—C10	1.386 (4)	C22—C23	1.384 (3)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.372 (4)	C23—H23	0.9300
C10—H10	0.9300	C24—N2	1.138 (3)
C11—C12	1.364 (4)	C25—O4	1.402 (3)
C11—C14	1.515 (5)	C25—O5	1.417 (3)
C12—C13	1.361 (4)	C25—H25A	0.9700
C12—H12	0.9300	C25—H25B	0.9700
C13—H13	0.9300	N1—S1	1.6508 (16)
C14—H14A	0.9600	O2—S1	1.4272 (15)
C14—H14B	0.9600	O3—S1	1.4219 (15)

C6—C1—C2	119.32 (16)	C16—C15—H15A	109.1
C6—C1—N1	119.61 (14)	N1—C15—H15B	109.1
C2—C1—N1	120.99 (16)	C16—C15—H15B	109.1
C1—C2—C3	119.88 (19)	H15A—C15—H15B	107.8
C1—C2—H2	120.1	C17—C16—C24	123.01 (18)
C3—C2—H2	120.1	C17—C16—C15	121.67 (17)
C4—C3—C2	120.55 (18)	C24—C16—C15	115.16 (17)
C4—C3—H3	119.7	C16—C17—C18	132.02 (18)
C2—C3—H3	119.7	C16—C17—H17	114.0
C5—C4—C3	119.87 (19)	C18—C17—H17	114.0
C5—C4—H4	120.1	C23—C18—C19	118.69 (19)
C3—C4—H4	120.1	C23—C18—C17	117.08 (18)
C4—C5—C6	121.0 (2)	C19—C18—C17	124.10 (18)
C4—C5—H5	119.5	C20—C19—C18	117.3 (2)
C6—C5—H5	119.5	C20—C19—H19	121.3
C1—C6—C5	119.36 (17)	C18—C19—H19	121.3
C1—C6—C7	122.22 (18)	C19—C20—C21	122.8 (2)
C5—C6—C7	118.39 (19)	C19—C20—O5	127.7 (2)
O1—C7—C6	122.8 (3)	C21—C20—O5	109.6 (2)
O1—C7—H7	118.6	C22—C21—C20	121.6 (2)
C6—C7—H7	118.6	C22—C21—O4	128.4 (2)
C9—C8—C13	119.7 (2)	C20—C21—O4	110.0 (2)
C9—C8—S1	121.03 (17)	C21—C22—C23	116.7 (2)
C13—C8—S1	119.24 (19)	C21—C22—H22	121.7
C8—C9—C10	119.1 (2)	C23—C22—H22	121.7
C8—C9—H9	120.5	C18—C23—C22	122.9 (2)
C10—C9—H9	120.5	C18—C23—H23	118.5
C11—C10—C9	121.3 (3)	C22—C23—H23	118.5
C11—C10—H10	119.3	N2—C24—C16	177.1 (2)
C9—C10—H10	119.3	O4—C25—O5	109.1 (2)
C12—C11—C10	118.2 (3)	O4—C25—H25A	109.9
C12—C11—C14	121.5 (4)	O5—C25—H25A	109.9
C10—C11—C14	120.3 (4)	O4—C25—H25B	109.9
C13—C12—C11	122.1 (3)	O5—C25—H25B	109.9
C13—C12—H12	118.9	H25A—C25—H25B	108.3
C11—C12—H12	118.9	C1—N1—C15	118.17 (14)
C12—C13—C8	119.6 (3)	C1—N1—S1	116.13 (11)
C12—C13—H13	120.2	C15—N1—S1	117.24 (12)
C8—C13—H13	120.2	C21—O4—C25	105.78 (19)
C11—C14—H14A	109.5	C20—O5—C25	105.5 (2)
C11—C14—H14B	109.5	O3—S1—O2	119.87 (9)
H14A—C14—H14B	109.5	O3—S1—N1	106.60 (9)
C11—C14—H14C	109.5	O2—S1—N1	105.69 (9)
H14A—C14—H14C	109.5	O3—S1—C8	108.38 (10)
H14B—C14—H14C	109.5	O2—S1—C8	108.60 (10)
N1—C15—C16	112.49 (15)	N1—S1—C8	107.01 (8)
N1—C15—H15A	109.1

C6—C1—C2—C3	−0.1 (3)	O5—C20—C21—C22	177.8 (3)
N1—C1—C2—C3	176.75 (16)	C19—C20—C21—O4	−178.8 (2)
C1—C2—C3—C4	−1.1 (3)	O5—C20—C21—O4	−0.2 (3)
C2—C3—C4—C5	1.2 (3)	C20—C21—C22—C23	0.6 (4)
C3—C4—C5—C6	−0.2 (3)	O4—C21—C22—C23	178.3 (2)
C2—C1—C6—C5	1.1 (3)	C19—C18—C23—C22	−1.4 (3)
N1—C1—C6—C5	−175.84 (17)	C17—C18—C23—C22	−177.4 (2)
C2—C1—C6—C7	−177.0 (2)	C21—C22—C23—C18	0.5 (4)
N1—C1—C6—C7	6.1 (3)	C17—C16—C24—N2	152 (6)
C4—C5—C6—C1	−0.9 (3)	C15—C16—C24—N2	−32 (6)
C4—C5—C6—C7	177.2 (2)	C6—C1—N1—C15	−130.68 (18)
C1—C6—C7—O1	−169.7 (3)	C2—C1—N1—C15	52.5 (2)
C5—C6—C7—O1	12.2 (5)	C6—C1—N1—S1	82.06 (19)
C13—C8—C9—C10	0.3 (3)	C2—C1—N1—S1	−94.77 (18)
S1—C8—C9—C10	−177.96 (18)	C16—C15—N1—C1	85.0 (2)
C8—C9—C10—C11	−0.2 (4)	C16—C15—N1—S1	−128.14 (15)
C9—C10—C11—C12	0.1 (4)	C22—C21—O4—C25	−179.4 (3)
C9—C10—C11—C14	179.0 (3)	C20—C21—O4—C25	−1.6 (3)
C10—C11—C12—C13	0.0 (4)	O5—C25—O4—C21	2.8 (3)
C14—C11—C12—C13	−178.9 (3)	C19—C20—O5—C25	−179.6 (3)
C11—C12—C13—C8	0.1 (4)	C21—C20—O5—C25	1.9 (3)
C9—C8—C13—C12	−0.2 (3)	O4—C25—O5—C20	−2.9 (3)
S1—C8—C13—C12	178.05 (19)	C1—N1—S1—O3	−172.54 (13)
N1—C15—C16—C17	−135.66 (18)	C15—N1—S1—O3	39.89 (16)
N1—C15—C16—C24	48.7 (2)	C1—N1—S1—O2	−43.97 (14)
C24—C16—C17—C18	4.2 (3)	C15—N1—S1—O2	168.46 (13)
C15—C16—C17—C18	−171.09 (18)	C1—N1—S1—C8	71.65 (14)
C16—C17—C18—C23	−174.4 (2)	C15—N1—S1—C8	−75.91 (15)
C16—C17—C18—C19	9.9 (3)	C9—C8—S1—O3	−26.56 (19)
C23—C18—C19—C20	1.2 (3)	C13—C8—S1—O3	155.17 (17)
C17—C18—C19—C20	176.9 (2)	C9—C8—S1—O2	−158.29 (16)
C18—C19—C20—C21	−0.2 (4)	C13—C8—S1—O2	23.45 (19)
C18—C19—C20—O5	−178.5 (2)	C9—C8—S1—N1	88.05 (17)
C19—C20—C21—C22	−0.8 (4)	C13—C8—S1—N1	−90.22 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O3	0.97	2.40	2.879 (3)	110
C15—H15B···O2ⁱ	0.97	2.42	3.282 (3)	148
C23—H23···O1ⁱⁱ	0.93	2.41	3.114 (3)	132
C4—H4···O3ⁱⁱⁱ	0.93	2.59	3.195 (3)	124
C25—H25A···Cg1^iv	0.97	2.96	3.446 (4)	112

Symmetry codes: (i) −x+5/2, y−1/2, −z+3/2; (ii) x, y−1, z; (iii) x−1, y, z; (iv) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₀N₂O₅S
M_r	460.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.921 (5), 10.235 (4), 25.256 (3)
β (°)	93.380 (4)
V (Å³)	2302.0 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.23 × 0.21 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.959, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	26810, 6451, 3582
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.696

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.148, 1.01
No. of reflections	6451
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.28

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).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O3	0.97	2.40	2.879 (3)	110.0
C15—H15B···O2ⁱ	0.97	2.42	3.282 (3)	147.5
C23—H23···O1ⁱⁱ	0.93	2.41	3.114 (3)	132.1
C4—H4···O3ⁱⁱⁱ	0.93	2.59	3.195 (3)	123.5
C25—H25A···Cg1^iv	0.97	2.96	3.446 (4)	112.0

Symmetry codes: (i) −x+5/2, y−1/2, −z+3/2; (ii) x, y−1, z; (iii) x−1, y, z; (iv) −x+2, −y, −z+1.

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

Arndt, F. & Franke, H. (1977). DE Patent No. 2624822. Google Scholar
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
Bassindale, A. (1984). The Third Dimension in Organic Chemistry. New York: John Wiley and Sons. 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
Gates, P. S. & Gillon, J. (1974). US Patent No. 3 736 338. Google Scholar
Jae, H.-S., Win, M., von Geldern, T. W., Sorensen, B. K., Chiou, W. J., Nguyen, B., Marsh, K. C. & Opgenorth, T. J. (2001). J. Med. Chem. 44, 3978–3984. Web of Science CrossRef PubMed CAS Google Scholar
Joshi, R., Kumar, M. S., Satyamoorthy, K., Unnikrisnan, M. K. & Mukherjee, T. (2005). J. Agric. Food Chem. 53, 2696–2703. Web of Science CrossRef PubMed CAS Google Scholar
Korolkovas, A. (1988). In Essentials of Medicinal Chemistry, 2nd ed., pp. 699–716. New York: Wiley. Google Scholar
Leite, A. C. L., Peixoto da Silva, K., de Souza, I. A., Magali de Araujo, J. & Brondani, D. J. (2004). Eur. J. Med. Chem. 39, 1059–1065. Web of Science CrossRef PubMed CAS Google Scholar
Madhanraj, R., Murugavel, S., Kannan, D. & Bakthadoss, M. (2011). Acta Cryst. E67, o3511. Web of Science CSD CrossRef 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
Ullrich, T., Baumann, K., Welzenbach, K., Schmutz, S., Camenish, G., Meingassner, J. G. & Weitz-Schmidt, G. (2004). Bioorg. Med. Chem. Lett. 14, 2483–2487. CrossRef PubMed CAS 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3164-o3165

doi:10.1107/S1600536812042663

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-3-(1,3-Benzodioxol-5-yl)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfon­amido]methyl}prop-2-ene­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

(E)-3-(1,3-Benzodioxol-5-yl)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfonamido]methyl}prop-2-enenitrile