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

In the title compound, C(25)H(20)N(2)O(5)S, 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 R(3) (3)(19) ring motifs. In addition, a weak π-π inter-action [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 = 460.49

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.148

S = 1.01

6451 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.28 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042663/bt6843sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042663/bt6843Isup3.cml

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

C25H20N2O5S	F(000) = 960
Mr = 460.49	Dx = 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

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

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(Fo2) + (0.061P)2 + 0.4367P] where P = (Fo2 + 2Fc2)/3
6451 reflections	(Δ/σ)max = 0.001
299 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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
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)

	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)

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)

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···Cg1iv	0.97	2.96	3.446 (4)	112

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) ; (ii) ; (iii) .