N-[(1,3-Benzodioxol-5-yl)meth-yl]benzene-sulfonamide: an analogue of capsaicin.

The title compound, C14H13NO4S, an analogue of capsaicin, differs from the latter by having a 1,3-benzodioxole ring rather than a 2-meth-oxy-phenol moiety, and having a benzene-sulfonamide group instead of an aliphatic amide chain. The five-membered ring is in an envelope conformation with the methyl-ene C atom lying 0.221 (6) Å out of the plane formed by the other four atoms. The dihedral angle between the phenyl ring and the mean plane of the 1,3-benzodioxole fused-ring system is 84.65 (4)°. In the crystal, mol-ecules aggregate into supra-molecular layers in the ac plane through C-H⋯O, N-H⋯O and C-H⋯π inter-actions.

Related literature

For background and the biological activity of capsaicin, see: Lee et al. (2011 ▶); Malagarie-Cazenave et al. (2011 ▶). For the synthesis and cytoxicity of the title compound, see: De Sá-Junior et al. (2013 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H13NO4S

M = 291.32

Orthorhombic,

a = 18.0158 (4) Å

b = 5.9346 (1) Å

c = 25.5480 (8) Å

V = 2731.51 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 290 K

0.25 × 0.22 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer with Bruker APEXII CCD areadetector

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.930, T max = 0.948

2652 measured reflections

2652 independent reflections

1860 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.149

S = 1.04

2652 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813028481/tk5268sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028481/tk5268Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028481/tk5268Isup3.cml

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

C14H13NO4S	Dx = 1.417 Mg m−3
Mr = 291.32	Melting point = 350.1–350.6 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3351 reflections
a = 18.0158 (4) Å	θ = 1.4–27.1°
b = 5.9346 (1) Å	µ = 0.25 mm−1
c = 25.5480 (8) Å	T = 290 K
V = 2731.51 (11) Å3	Irregular, colourless
Z = 8	0.25 × 0.22 × 0.20 mm
F(000) = 1216

Nonius KappaCCD with Bruker APEXII CCD area detector diffractometer	2652 independent reflections
Radiation source: fine-focus sealed tube	1860 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = 0→22
Tmin = 0.930, Tmax = 0.948	k = 0→7
2652 measured reflections	l = −31→0

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0843P)2 + 0.6245P] where P = (Fo2 + 2Fc2)/3
2652 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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
C1	0.14422 (14)	0.0794 (4)	0.26877 (9)	0.0610 (6)
H1A	0.1939	0.1190	0.2574	0.073*
H1B	0.1283	−0.0507	0.2487	0.073*
C2	0.14588 (11)	0.0187 (4)	0.32636 (9)	0.0493 (5)
C3	0.17158 (12)	−0.1926 (4)	0.34057 (10)	0.0561 (6)
H3	0.1836	−0.2958	0.3145	0.067*
C4	0.17986 (13)	−0.2546 (4)	0.39256 (10)	0.0596 (6)
H4	0.1975	−0.3962	0.4019	0.071*
C5	0.16096 (13)	−0.0985 (4)	0.42922 (9)	0.0550 (6)
C6	0.13417 (14)	0.1100 (4)	0.41568 (9)	0.0559 (6)
C7	0.12552 (13)	0.1742 (4)	0.36469 (8)	0.0547 (6)
H7	0.1069	0.3154	0.3559	0.066*
C8	0.1485 (2)	0.1023 (6)	0.50195 (12)	0.0966 (11)
H8A	0.1936	0.1721	0.5148	0.116*
H8B	0.1132	0.0948	0.5306	0.116*
C9	0.09760 (11)	0.2425 (4)	0.15195 (8)	0.0492 (5)
C10	0.02961 (13)	0.2300 (4)	0.12712 (10)	0.0625 (6)
H10	−0.0093	0.3224	0.1377	0.075*
C11	0.01987 (15)	0.0799 (5)	0.08658 (11)	0.0748 (8)
H11	−0.0258	0.0719	0.0697	0.090*
C12	0.07628 (17)	−0.0566 (5)	0.07097 (11)	0.0805 (8)
H12	0.0689	−0.1577	0.0436	0.097*
C13	0.14451 (16)	−0.0459 (5)	0.09547 (11)	0.0806 (9)
H13	0.1830	−0.1390	0.0845	0.097*
C14	0.15560 (13)	0.1045 (5)	0.13662 (10)	0.0647 (7)
H14	0.2013	0.1120	0.1535	0.078*
O1	0.18306 (9)	0.4975 (3)	0.20769 (7)	0.0703 (5)
O2	0.04895 (10)	0.5823 (3)	0.20637 (6)	0.0654 (5)
O3	0.16399 (11)	−0.1167 (3)	0.48341 (7)	0.0764 (6)
O4	0.11841 (13)	0.2327 (3)	0.46019 (6)	0.0841 (6)
N1	0.09406 (10)	0.2681 (3)	0.25825 (7)	0.0558 (5)
H1N	0.0405	0.2323	0.2630	0.067*
S1	0.10836 (3)	0.42069 (10)	0.20672 (2)	0.0518 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0711 (16)	0.0610 (14)	0.0509 (14)	0.0106 (12)	0.0004 (11)	−0.0038 (11)
C2	0.0490 (12)	0.0500 (13)	0.0487 (13)	−0.0012 (10)	0.0018 (9)	−0.0018 (10)
C3	0.0558 (13)	0.0492 (14)	0.0632 (15)	0.0037 (10)	0.0044 (11)	−0.0060 (11)
C4	0.0576 (14)	0.0483 (12)	0.0728 (17)	0.0033 (11)	−0.0017 (12)	0.0047 (11)
C5	0.0579 (13)	0.0551 (13)	0.0519 (13)	−0.0040 (10)	−0.0008 (10)	0.0085 (11)
C6	0.0698 (15)	0.0511 (13)	0.0467 (13)	0.0008 (11)	0.0029 (11)	−0.0035 (10)
C7	0.0679 (14)	0.0463 (12)	0.0497 (13)	0.0031 (11)	0.0018 (11)	0.0017 (10)
C8	0.156 (3)	0.084 (2)	0.0500 (16)	0.010 (2)	−0.0048 (18)	0.0069 (15)
C9	0.0487 (12)	0.0559 (12)	0.0431 (12)	0.0012 (10)	0.0049 (9)	0.0026 (9)
C10	0.0515 (13)	0.0768 (16)	0.0592 (14)	0.0030 (12)	0.0026 (11)	−0.0098 (12)
C11	0.0678 (17)	0.0909 (19)	0.0657 (17)	−0.0066 (14)	−0.0029 (13)	−0.0167 (15)
C12	0.099 (2)	0.0810 (18)	0.0619 (17)	0.0034 (17)	−0.0010 (15)	−0.0185 (14)
C13	0.091 (2)	0.089 (2)	0.0620 (17)	0.0302 (17)	0.0082 (15)	−0.0123 (15)
C14	0.0592 (14)	0.0821 (17)	0.0526 (14)	0.0156 (12)	−0.0001 (11)	−0.0023 (12)
O1	0.0522 (10)	0.0763 (12)	0.0823 (13)	−0.0131 (9)	0.0035 (8)	−0.0066 (9)
O2	0.0653 (11)	0.0623 (11)	0.0686 (11)	0.0126 (8)	0.0045 (8)	−0.0066 (8)
O3	0.1040 (14)	0.0704 (12)	0.0548 (11)	0.0079 (10)	−0.0014 (9)	0.0142 (8)
O4	0.1363 (18)	0.0690 (12)	0.0471 (10)	0.0244 (11)	−0.0015 (10)	−0.0023 (9)
N1	0.0522 (11)	0.0670 (12)	0.0482 (11)	0.0010 (9)	0.0026 (8)	0.0001 (9)
S1	0.0522 (4)	0.0525 (4)	0.0507 (4)	−0.0022 (2)	0.0016 (2)	−0.0017 (2)

C1—N1	1.464 (3)	C8—H8B	0.9700
C1—C2	1.515 (3)	C9—C10	1.382 (3)
C1—H1A	0.9700	C9—C14	1.384 (3)
C1—H1B	0.9700	C9—S1	1.765 (2)
C2—C3	1.385 (3)	C10—C11	1.377 (3)
C2—C7	1.395 (3)	C10—H10	0.9300
C3—C4	1.386 (3)	C11—C12	1.360 (4)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.361 (3)	C12—C13	1.381 (4)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.372 (3)	C13—C14	1.393 (4)
C5—O3	1.390 (3)	C13—H13	0.9300
C6—C7	1.366 (3)	C14—H14	0.9300
C6—O4	1.380 (3)	O1—S1	1.4210 (17)
C7—H7	0.9300	O2—S1	1.4372 (18)
C8—O3	1.411 (4)	N1—S1	1.6186 (19)
C8—O4	1.425 (3)	N1—H1N	0.9947
C8—H8A	0.9700
N1—C1—C2	111.85 (18)	C10—C9—C14	120.5 (2)
N1—C1—H1A	109.2	C10—C9—S1	119.57 (17)
C2—C1—H1A	109.2	C14—C9—S1	119.74 (18)
N1—C1—H1B	109.2	C11—C10—C9	119.5 (2)
C2—C1—H1B	109.2	C11—C10—H10	120.2
H1A—C1—H1B	107.9	C9—C10—H10	120.2
C3—C2—C7	120.2 (2)	C12—C11—C10	120.7 (2)
C3—C2—C1	118.4 (2)	C12—C11—H11	119.6
C7—C2—C1	121.3 (2)	C10—C11—H11	119.6
C2—C3—C4	121.8 (2)	C11—C12—C13	120.3 (3)
C2—C3—H3	119.1	C11—C12—H12	119.8
C4—C3—H3	119.1	C13—C12—H12	119.8
C5—C4—C3	116.9 (2)	C12—C13—C14	119.9 (2)
C5—C4—H4	121.6	C12—C13—H13	120.0
C3—C4—H4	121.6	C14—C13—H13	120.0
C4—C5—C6	121.9 (2)	C9—C14—C13	119.0 (2)
C4—C5—O3	128.5 (2)	C9—C14—H14	120.5
C6—C5—O3	109.6 (2)	C13—C14—H14	120.5
C7—C6—C5	122.1 (2)	C5—O3—C8	104.8 (2)
C7—C6—O4	128.0 (2)	C6—O4—C8	104.6 (2)
C5—C6—O4	109.9 (2)	C1—N1—S1	118.62 (15)
C6—C7—C2	117.0 (2)	C1—N1—H1N	114.4
C6—C7—H7	121.5	S1—N1—H1N	111.9
C2—C7—H7	121.5	O1—S1—O2	119.43 (12)
O3—C8—O4	108.9 (2)	O1—S1—N1	108.42 (11)
O3—C8—H8A	109.9	O2—S1—N1	105.06 (10)
O4—C8—H8A	109.9	O1—S1—C9	108.06 (10)
O3—C8—H8B	109.9	O2—S1—C9	108.26 (10)
O4—C8—H8B	109.9	N1—S1—C9	106.99 (11)
H8A—C8—H8B	108.3
N1—C1—C2—C3	160.6 (2)	C10—C9—C14—C13	0.5 (4)
N1—C1—C2—C7	−22.4 (3)	S1—C9—C14—C13	175.8 (2)
C7—C2—C3—C4	−1.8 (3)	C12—C13—C14—C9	−0.5 (4)
C1—C2—C3—C4	175.2 (2)	C4—C5—O3—C8	171.9 (3)
C2—C3—C4—C5	0.5 (3)	C6—C5—O3—C8	−8.6 (3)
C3—C4—C5—C6	0.7 (4)	O4—C8—O3—C5	14.5 (3)
C3—C4—C5—O3	−179.9 (2)	C7—C6—O4—C8	−171.0 (3)
C4—C5—C6—C7	−0.6 (4)	C5—C6—O4—C8	9.3 (3)
O3—C5—C6—C7	179.8 (2)	O3—C8—O4—C6	−14.8 (4)
C4—C5—C6—O4	179.0 (2)	C2—C1—N1—S1	155.52 (16)
O3—C5—C6—O4	−0.5 (3)	C1—N1—S1—O1	−53.6 (2)
C5—C6—C7—C2	−0.6 (4)	C1—N1—S1—O2	177.62 (16)
O4—C6—C7—C2	179.8 (2)	C1—N1—S1—C9	62.69 (19)
C3—C2—C7—C6	1.8 (3)	C10—C9—S1—O1	−149.4 (2)
C1—C2—C7—C6	−175.1 (2)	C14—C9—S1—O1	35.3 (2)
C14—C9—C10—C11	−0.4 (4)	C10—C9—S1—O2	−18.7 (2)
S1—C9—C10—C11	−175.7 (2)	C14—C9—S1—O2	165.94 (19)
C9—C10—C11—C12	0.3 (4)	C10—C9—S1—N1	94.0 (2)
C10—C11—C12—C13	−0.3 (5)	C14—C9—S1—N1	−81.3 (2)
C11—C12—C13—C14	0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.99	2.00	2.945 (3)	157
C14—H14···O1ii	0.93	2.59	3.486 (3)	161
C10—H10···Cg1iii	0.93	2.74	3.563 (3)	147
C8—H8B···Cg2iv	0.97	2.82	3.511 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.99	2.00	2.945 (3)	157
C14—H14⋯O1ii	0.93	2.59	3.486 (3)	161
C10—H10⋯Cg1iii	0.93	2.74	3.563 (3)	147
C8—H8B⋯Cg2iv	0.97	2.82	3.511 (3)	129

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .