2 Morpholino N (p tolyl­sulfon­yl)ethyl­amine

organic papers

o2826

13H20N2O3S doi:10.1107/S1600536805024657 Acta Cryst.(2005). E61, o2826–o2827

Acta Crystallographica Section E Structure Reports

Online

ISSN 1600-5368

2-Morpholino-

N

-(

p

-tolylsulfonyl)ethylamine

Tufan Akbal,aNesuhi Akdemir,b Erbil Ag˘arband

Ahmet Erdo¨nmeza*

a_{Department of Physics, Faculty of Arts and}

Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey, andb_{Department of Chemistry,} Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey

Correspondence e-mail: takbal@omu.edu.tr

Key indicators

Single-crystal X-ray study T= 290 K

Mean(C–C) = 0.004 A˚ Rfactor = 0.043 wRfactor = 0.108

Data-to-parameter ratio = 19.1

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2005 International Union of Crystallography

Printed in Great Britain – all rights reserved

In the crystal structure of the title compound, C13H20N2O3S, there are some inter- and intramolecular N—H O, N— H N and C—H O hydrogen-bonding interactions.

Comment

The title compound, (I), is a derivative of sulfonamide. Sulfonamide derivatives are generally used as antibiotics and photosensitizers for photodynamic therapy (PDT) (Strom et al., 2003; Maket al., 2003).

The molecular structure of (I) is shown in Fig. 1and selected geometric parameters are in Table 1. The S1—N1 bond length is in good agreement with data observed in the literature (O¨ ztu¨rket al., 2000). In the morpholine group, the C11—O3 and C12—O3 bond lengths are consistent with corresponding bonds [1.421 (3) and 1.424 (3) A˚ ] inerythro -2-morpholino-1,2-diphenylethanol (Karadayı et al., 2002). The N2—C10 and N2—C13 bond lengths agree with the corresponding values in 1-morpholinomethyl-2-naphthol (Maet al., 2005) anderythro -2-morpholino-1,2-diphenylethanol (Karadayıet al., 2002). The morpholine ring adopts a chair conformation, with puckering parameters of = 180.0 (2)_{, ’ = 259 (12) and Q}

T = 0.567 (2) A˚ (Cremer & Pople, 1975).

The crystal structure is stabilized by some inter- and intra-molecular N—H O, N—H N and C—H O hydrogen-bonding interactions (Fig. 2 and Table 2).

Experimental

2-Morpholinoethylamine (6.45 g, 49.61 mmol) and sodium hydroxide (2.10 g, 52.5 mmol) were dissolved in water (15 ml). A solution of toluene-p-sulfonyl chloride (10.15 g, 53.25 mmol) in diethyl ether was added dropwise over 2 h. The mixture was then stirred at room temperature for 10 h. The organic phase was dried over Na2SO4and

evaporated. The white product was washed with water and diethyl ether and recrystallization from ethanol gave the title product (yield 12.06 g, 85.05%). Single crystals were obtained from absolute ethanol at room temperature by slow evaporation (m.p. 372–373 K).

Crystal data

C13H20N2O3S

Mr= 284.37 Monoclinic,P21=c

a= 13.7639 (14) A˚

b= 8.0723 (7) A˚

c= 14.1519 (15) A˚

= 109.028 (8)

V= 1486.5 (3) A˚3

Z= 4

Dx= 1.271 Mg m

3

MoKradiation Cell parameters from 8322

reflections

= 2.5–27.4

= 0.22 mm1

T= 290 (2) K Prism, colourless 0.580.380.13 mm

Data collection

Stoe IPDS-2 diffractometer

!scans

Absorption correction: integration (X-RED32; Stoe & Cie, 2002)

Tmin= 0.975,Tmax= 0.987 9234 measured reflections 3303 independent reflections

1888 reflections withI> 2(I)

Rint= 0.056

max= 27.4

h=17!17

k=10!7

l=18!18

Refinement

Refinement onF2

R[F2_{> 2(F}2_{)] = 0.043}

wR(F2_{) = 0.108}

S= 0.90 3303 reflections 173 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0563P)2] whereP= (Fo2+ 2Fc2)/3 (/)max= 0.001

max= 0.31 e A˚

3

min=0.24 e A˚

3

Extinction correction:SHELXL97

Extinction coefficient: 0.026 (2)

Table 1

Selected geometric parameters (A˚ ,_).

S1—O1 1.4217 (16) S1—O2 1.4273 (18) S1—N1 1.5966 (18) N2—C10 1.454 (3)

N2—C13 1.460 (2) O3—C12 1.419 (3) O3—C11 1.429 (3)

O1—S1—O2 119.78 (12) N1—S1—C1 108.51 (9)

C10—N2—C13 108.86 (17) C12—O3—C11 109.70 (16)

O1—S1—N1—C8 43.81 (19) O2—S1—N1—C8 172.99 (16)

C1—S1—N1—C8 72.04 (17)

Table 2

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

N1—H4 O3i

0.86 2.20 2.916 (2) 140 C5—H5 O1ii 0.93 2.55 3.248 (3) 132 N1—H4 N2 0.86 2.61 2.906 (2) 102 C8—H12B O1 0.97 2.51 2.949 (3) 107

Symmetry codes: (i)xþ2;yþ1 2;zþ

3

2; (ii)x;yþ 1 2;z

1 2.

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 A˚ , and withUiso(H) constrained to be 1.2 (or 1.5 for methyl H atoms) timesUeqof the carrier atom.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement:

X-AREA; data reduction:X-RED32(Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999) and

PARST(Nardelli, 1995).

References

Burnett, M. N. & Johnson, C. K. (1996).ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.

Cremer, D. & Pople, J. A. (1975).J. Am. Chem. Soc.97, 1354–1358. Farrugia, L. J. (1999).J. Appl. Cryst.32, 837–838.

Karadayı, N., Kazak, C., O¨ ztu¨rk, S., Aydın, M., Arsu, N., Fun, H.-K. & Bu¨yu¨kgu¨ngo¨r, O. (2002).Acta Cryst.E58, o1152–o1153.

Ma, S.-S., Zhang, M.-J., Yuan, D.-Y. & Qi, Z.-B. (2005).Acta Cryst.E61, o1370– o1371.

Mak, N. K., Kok, T. W., Wong, R. N. S., Lam, S. W., Lau, Y. K., Leung, W. N., Cheung, N. H., Huang, D. P., Yeung, L. L. & Chang, C. K. (2003).J. Biomed. Sci.10, 418–429.

Nardelli, M. (1995).J. Appl. Cryst.28, 659.

O¨ ztu¨rk, S., Is¸ık, S¸., Ag˘ar, E., S¸as¸maz, S¸., Fun, H. K. & Erdonmez, A. (2000).

Spectrosc. Lett.33, 245–254.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.

Stoe & Cie (2002).X-AREA(Version 1.18) andX-RED32(Version 1.04). Stoe & Cie, Darmstadt, Germany.

Strom, B. L., Schinnar, R., Apter, A. J., Margolis, D. J., Lautenbach, E., Figure 2

A view of the hydrogen-bonding interactions (dashed lines) in (I). Figure 1

supporting information

sup-1 Acta Cryst. (2005). E61, o2826–o2827

supporting information

Acta Cryst. (2005). E61, o2826–o2827 [https://doi.org/10.1107/S1600536805024657]

2-Morpholino-

N

-(

p

-tolylsulfonyl)ethylamine

Tufan Akbal, Nesuhi Akdemir, Erbil A

ğ

ar and Ahmet Erd

ö

nmez

2-Morpholino-N-(p-tolylsulfonyl)ethylamine

Crystal data C13H20N2O3S

Mr = 284.37

Monoclinic, P21/c

Hall symbol: -P 2ybc a = 13.7639 (14) Å b = 8.0723 (7) Å c = 14.1519 (15) Å β = 109.028 (8)° V = 1486.5 (3) Å3

Z = 4

F(000) = 608 Dx = 1.271 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 8322 reflections θ = 2.5–27.4°

µ = 0.22 mm−1

T = 290 K Prism, colourless 0.58 × 0.38 × 0.13 mm

Data collection Stoe IPDS-2

diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

Detector resolution: 6.67 pixels mm-1

ω scans

Absorption correction: integration (X-RED32; Stoe & Cie, 2002) Tmin = 0.975, Tmax = 0.987

9234 measured reflections 3303 independent reflections 1888 reflections with I > 2σ(I) Rint = 0.056

θmax = 27.4°, θmin = 2.9°

h = −17→17 k = −10→7 l = −18→18

Refinement Refinement on F2

Least-squares matrix: full R[F2 _{> 2σ(F}2_{)] = 0.043}

wR(F2_{) = 0.108}

S = 0.90 3303 reflections 173 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2_(F

o2) + (0.0563P)2]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001

Δρmax = 0.31 e Å−3

Δρmin = −0.24 e Å−3

Extinction correction: SHELXL97, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2θ)]-1/4

Special details

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 F}2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

supporting information

sup-3 Acta Cryst. (2005). E61, o2826–o2827

C7 0.3564 (3) 0.1749 (5) 0.4568 (2) 0.1170 (12) H7A 0.3722 0.2407 0.4072 0.176* H7B 0.2961 0.2180 0.4679 0.176* H7C 0.3442 0.0624 0.4339 0.176*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

S1 0.0524 (3) 0.0634 (4) 0.0719 (3) 0.0042 (3) 0.0205 (2) −0.0146 (3) N2 0.0532 (10) 0.0513 (9) 0.0470 (8) 0.0060 (8) 0.0188 (7) 0.0018 (6) N1 0.0452 (10) 0.0596 (11) 0.0793 (10) 0.0028 (8) 0.0309 (8) 0.0005 (8) C1 0.0459 (12) 0.0512 (11) 0.0666 (11) 0.0050 (10) 0.0252 (9) −0.0043 (9) O3 0.0643 (10) 0.0652 (9) 0.0717 (9) 0.0108 (8) 0.0289 (8) −0.0055 (7) C10 0.0658 (14) 0.0742 (15) 0.0526 (10) 0.0135 (12) 0.0168 (10) 0.0044 (10) O1 0.0749 (11) 0.1256 (16) 0.0675 (9) 0.0183 (10) 0.0330 (8) −0.0182 (9) C12 0.0753 (15) 0.0678 (14) 0.0545 (11) 0.0027 (12) 0.0265 (11) −0.0049 (10) O2 0.0674 (11) 0.0589 (11) 0.1280 (14) −0.0078 (8) 0.0129 (10) −0.0205 (9) C2 0.0598 (15) 0.0663 (14) 0.0766 (14) −0.0038 (12) 0.0261 (12) 0.0073 (11) C13 0.0616 (14) 0.0667 (14) 0.0578 (10) 0.0001 (11) 0.0171 (10) −0.0084 (10) C6 0.0543 (14) 0.0817 (17) 0.0860 (15) 0.0006 (12) 0.0360 (13) 0.0094 (12) C9 0.0695 (14) 0.0610 (13) 0.0641 (11) 0.0076 (11) 0.0333 (11) 0.0105 (10) C11 0.0577 (14) 0.0757 (16) 0.0678 (12) 0.0079 (12) 0.0170 (10) −0.0058 (11) C4 0.0609 (15) 0.0864 (18) 0.0716 (14) 0.0144 (13) 0.0186 (11) −0.0128 (12) C3 0.0530 (15) 0.0713 (16) 0.0955 (17) −0.0086 (12) 0.0171 (13) −0.0030 (13) C5 0.0738 (18) 0.111 (2) 0.0694 (14) 0.0200 (15) 0.0369 (14) 0.0179 (13) C8 0.0569 (14) 0.0640 (14) 0.0771 (13) −0.0042 (11) 0.0331 (11) −0.0015 (11) C7 0.098 (2) 0.154 (3) 0.0803 (17) 0.029 (2) 0.0029 (16) −0.0236 (19)

Geometric parameters (Å, º)

C12—H10B 0.9700 C7—H7B 0.9600 C2—C3 1.375 (3) C7—H7C 0.9600

O1—S1—O2 119.78 (12) C5—C6—C1 119.9 (2) O1—S1—N1 107.25 (10) C5—C6—H6 120.1 O2—S1—N1 106.21 (10) C1—C6—H6 120.1 O1—S1—C1 107.50 (10) N2—C9—C8 113.28 (16) O2—S1—C1 107.21 (11) N2—C9—H13A 108.9 N1—S1—C1 108.51 (9) C8—C9—H13A 108.9 C10—N2—C9 110.84 (15) N2—C9—H13B 108.9 C10—N2—C13 108.86 (17) C8—C9—H13B 108.9 C9—N2—C13 111.75 (17) H13A—C9—H13B 107.7 C8—N1—S1 121.54 (14) O3—C11—C10 110.50 (19) C8—N1—H4 119.2 O3—C11—H9A 109.6 S1—N1—H4 119.2 C10—C11—H9A 109.6 C6—C1—C2 119.4 (2) O3—C11—H9B 109.6 C6—C1—S1 120.28 (17) C10—C11—H9B 109.6 C2—C1—S1 120.35 (16) H9A—C11—H9B 108.1 C12—O3—C11 109.70 (16) C3—C4—C5 118.2 (2) N2—C10—C11 111.17 (16) C3—C4—C7 121.0 (3) N2—C10—H8A 109.4 C5—C4—C7 120.8 (3) C11—C10—H8A 109.4 C4—C3—C2 121.1 (2) N2—C10—H8B 109.4 C4—C3—H3 119.4 C11—C10—H8B 109.4 C2—C3—H3 119.4 H8A—C10—H8B 108.0 C6—C5—C4 121.4 (2) O3—C12—C13 111.90 (16) C6—C5—H5 119.3 O3—C12—H10A 109.2 C4—C5—H5 119.3 C13—C12—H10A 109.2 N1—C8—C9 110.61 (18) O3—C12—H10B 109.2 N1—C8—H12A 109.5 C13—C12—H10B 109.2 C9—C8—H12A 109.5 H10A—C12—H10B 107.9 N1—C8—H12B 109.5 C1—C2—C3 120.0 (2) C9—C8—H12B 109.5 C1—C2—H2 120.0 H12A—C8—H12B 108.1 C3—C2—H2 120.0 C4—C7—H7A 109.5 N2—C13—C12 110.43 (18) C4—C7—H7B 109.5 N2—C13—H11A 109.6 H7A—C7—H7B 109.5 C12—C13—H11A 109.6 C4—C7—H7C 109.5 N2—C13—H11B 109.6 H7A—C7—H7C 109.5 C12—C13—H11B 109.6 H7B—C7—H7C 109.5 H11A—C13—H11B 108.1

supporting information

sup-5 Acta Cryst. (2005). E61, o2826–o2827

O2—S1—C1—C2 −155.37 (18) C5—C4—C3—C2 0.1 (4) N1—S1—C1—C2 90.31 (18) C7—C4—C3—C2 −179.9 (2) C9—N2—C10—C11 −179.78 (19) C1—C2—C3—C4 0.3 (4) C13—N2—C10—C11 56.9 (2) C1—C6—C5—C4 0.4 (4) C11—O3—C12—C13 −58.2 (2) C3—C4—C5—C6 −0.4 (4) C6—C1—C2—C3 −0.3 (3) C7—C4—C5—C6 179.5 (2) S1—C1—C2—C3 −178.63 (18) S1—N1—C8—C9 −144.44 (15) C10—N2—C13—C12 −55.4 (2) N2—C9—C8—N1 −58.1 (2) C9—N2—C13—C12 −178.18 (17)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A N1—H4···O3i _{0.86 2.20 2.916 (2) 140}

C5—H5···O1ii _{0.93 2.55 3.248 (3) 132}

N1—H4···N2 0.86 2.61 2.906 (2) 102 C8—H12B···O1 0.97 2.51 2.949 (3) 107