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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o174.
Published online 2007 December 6. doi:  10.1107/S1600536807063805
PMCID: PMC2915238

Bis[4-(2-hydroxy­ethyl­amino)phen­yl] sulfone

Abstract

The title compound, C16H20N2O4S, exhibits a V-shape structure with a dihedral angle of 77.5 (11)° formed by the two benzenel rings. The mol­ecular packing is stabilized by intra­molecular and inter­molecular hydrogen bonds as well as π–π [3.738 (3) Å] and C—H(...)π inter­actions.

Related literature

For related literature, see: Shahsafi et al. (1987 [triangle]).

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Object name is e-64-0o174-scheme1.jpg

Experimental

Crystal data

  • C16H20N2O4S
  • M r = 336.40
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o174-efi1.jpg
  • a = 25.643 (17) Å
  • b = 8.118 (6) Å
  • c = 15.340 (11) Å
  • β = 102.989 (12)°
  • V = 3112 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 294 (2) K
  • 0.20 × 0.18 × 0.16 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.953, T max = 0.966
  • 7793 measured reflections
  • 2742 independent reflections
  • 1982 reflections with I > 2σ
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.110
  • S = 1.03
  • 2742 reflections
  • 218 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063805/bx2122sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063805/bx2122Isup2.hkl

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

supplementary crystallographic information

Comment

The derivatives of diphenyl sulphone are used as precursors in the organic synthesis. Several derivatives of aminosulphones have been shown to possess strong tuberculostatic, antileprotic and anticonvulsant activities (Shahsafi, et al., 1987). The crystal structure determination of the title compound, (I), was carried out in order to elucidate its molecular conformation.

The V-shape structure of the molecule is supported by the two phenyl rings with a dihedral angle of 77.5 (11)°.

The molecular packing is stabilized by intramolecular and intermolecular hydrogen bonds (Table 1) as well as weak π-π and C—H..π interactions.

Experimental

The title compound, (I), was synthesized by the reaction of 4,4'-dichlorodiphenyl sulfone (5.74 g, 0.02 mol) with 2-aminoethanol (9.76 g, 0.16 mol). The mixture was refluxed for 6 h and cooled to room temperature. After dilution with water, it was filtered off, washed thoroughly with water, and recrystallized from dimethylformamide and water (4:1 v/v) to give the product as fine white needles (5.5 g, yield 81.8%). The pure product (0.1 g) was dissolved in 15 ml dimethylformamide and water (4:1 v/v). Single crystals were obtained from this solution by slow evaporation over a period of 7 days at room temperature (m.p. 464–466 K).

Refinement

The H atom involved in the hydrogen bonds was found in difference Fourier maps. All other H atoms were positioned geometrically and refined using a during refinement, fix at O–H distances of 0.82 Å and its Uiso value was set at 1.2 Ueq (O). H atoms bonded to C atoms were included in the refinement in the riding model approximation, with C–H = 0.93 Å. and Uiso (H) = 1.2 Ueq (C atom).

Figures

Fig. 1.
A view of the structure of (I), showing the atom-numbering Scheme; displacement ellipsoids were drawn at the 30% probability level.

Crystal data

C16H20N2O4SF000 = 1424
Mr = 336.40Dx = 1.436 Mg m3
Monoclinic, C2/cMelting point: 465(1) K
Hall symbol: -C 2ycMo Kα radiation λ = 0.71073 Å
a = 25.643 (17) ÅCell parameters from 2679 reflections
b = 8.118 (6) Åθ = 2.6–26.4º
c = 15.340 (11) ŵ = 0.23 mm1
β = 102.989 (12)ºT = 294 (2) K
V = 3112 (4) Å3Needle, colorless
Z = 80.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer2742 independent reflections
Radiation source: fine-focus sealed tube1982 reflections with I > 2σ
Monochromator: graphiteRint = 0.033
T = 294(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −26→30
Tmin = 0.953, Tmax = 0.966k = −9→9
7793 measured reflectionsl = −15→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110  w = 1/[σ2(Fo2) + (0.055P)2 + 1.5895P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.005
2742 reflectionsΔρmax = 0.22 e Å3
218 parametersΔρmin = −0.34 e Å3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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 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.

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

xyzUiso*/Ueq
S10.13804 (2)0.13061 (7)0.27577 (4)0.0437 (2)
O1−0.11464 (7)0.7991 (2)0.07807 (12)0.0614 (5)
H1−0.11530.84960.12410.092*
O20.16477 (7)0.1933 (2)0.36085 (10)0.0575 (5)
O30.11181 (7)−0.0265 (2)0.27233 (11)0.0551 (5)
O40.37876 (7)−0.1123 (3)0.00979 (13)0.0656 (5)
H40.3659−0.16330.04600.098*
N1−0.02318 (8)0.5964 (3)0.09390 (13)0.0496 (5)
N20.29293 (8)0.0802 (3)0.05074 (14)0.0479 (5)
C1−0.06999 (11)0.8469 (3)0.04713 (18)0.0605 (7)
H1A−0.06670.96590.05040.073*
H1B−0.07490.8150−0.01510.073*
C2−0.01965 (10)0.7710 (3)0.09995 (18)0.0541 (7)
H2A0.01060.80890.07710.065*
H2B−0.01400.80450.16210.065*
C30.01441 (8)0.4931 (3)0.13841 (14)0.0395 (5)
C40.06235 (9)0.5465 (3)0.19253 (16)0.0455 (6)
H4A0.06920.65880.19960.055*
C50.09948 (9)0.4366 (3)0.23534 (16)0.0452 (6)
H50.13140.47430.27120.054*
C60.09002 (8)0.2708 (3)0.22587 (14)0.0370 (5)
C70.04241 (9)0.2161 (3)0.17295 (15)0.0436 (6)
H70.03580.10360.16640.052*
C80.00543 (9)0.3235 (3)0.13085 (15)0.0449 (6)
H8−0.02670.28440.09610.054*
C90.18453 (8)0.1155 (3)0.21042 (14)0.0380 (5)
C100.23154 (9)0.2043 (3)0.23028 (15)0.0441 (6)
H100.23890.27290.28010.053*
C110.26711 (9)0.1918 (3)0.17704 (16)0.0450 (6)
H110.29890.25100.19140.054*
C120.25677 (9)0.0920 (3)0.10144 (14)0.0378 (5)
C130.20852 (8)0.0063 (3)0.08150 (15)0.0407 (5)
H130.2002−0.05930.03050.049*
C140.17353 (9)0.0173 (3)0.13568 (15)0.0424 (6)
H140.1418−0.04230.12210.051*
C150.28658 (9)−0.0244 (3)−0.02587 (15)0.0465 (6)
H15A0.25950.0214−0.07430.056*
H15B0.2745−0.1321−0.01150.056*
C160.33752 (10)−0.0418 (4)−0.05525 (17)0.0554 (7)
H16A0.3313−0.1096−0.10870.066*
H16B0.34890.0661−0.07090.066*
H1C−0.0542 (6)0.548 (3)0.0693 (15)0.053 (7)*
H2C0.3197 (7)0.153 (2)0.0623 (15)0.049 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0429 (3)0.0529 (4)0.0352 (3)0.0069 (3)0.0084 (2)0.0087 (3)
O10.0496 (10)0.0687 (12)0.0647 (12)0.0064 (9)0.0100 (9)−0.0226 (10)
O20.0570 (10)0.0800 (13)0.0318 (9)0.0134 (10)0.0023 (8)0.0028 (8)
O30.0590 (10)0.0523 (10)0.0570 (11)−0.0009 (9)0.0190 (9)0.0179 (8)
O40.0422 (10)0.0902 (15)0.0653 (12)0.0090 (10)0.0144 (9)0.0052 (11)
N10.0434 (12)0.0531 (13)0.0481 (12)0.0080 (11)0.0016 (10)−0.0008 (10)
N20.0427 (11)0.0510 (12)0.0521 (12)−0.0059 (10)0.0150 (10)−0.0089 (10)
C10.0681 (18)0.0621 (17)0.0520 (16)0.0196 (15)0.0147 (14)0.0100 (14)
C20.0517 (15)0.0544 (16)0.0578 (16)0.0082 (13)0.0157 (12)0.0068 (13)
C30.0367 (12)0.0505 (14)0.0329 (12)0.0077 (11)0.0113 (10)0.0001 (10)
C40.0424 (13)0.0445 (14)0.0500 (14)0.0024 (11)0.0111 (11)0.0014 (11)
C50.0362 (12)0.0540 (15)0.0442 (13)−0.0014 (11)0.0064 (10)0.0011 (11)
C60.0331 (11)0.0470 (13)0.0325 (11)0.0049 (10)0.0103 (9)0.0036 (10)
C70.0421 (13)0.0457 (14)0.0436 (13)0.0019 (12)0.0110 (11)−0.0027 (11)
C80.0359 (12)0.0553 (15)0.0413 (13)0.0018 (11)0.0043 (10)−0.0075 (11)
C90.0347 (11)0.0411 (12)0.0361 (12)0.0082 (10)0.0034 (9)0.0048 (10)
C100.0430 (13)0.0439 (14)0.0426 (13)0.0038 (11)0.0040 (10)−0.0037 (11)
C110.0371 (12)0.0441 (13)0.0518 (15)−0.0028 (11)0.0060 (11)−0.0040 (12)
C120.0361 (11)0.0375 (12)0.0386 (12)0.0050 (10)0.0059 (10)0.0038 (10)
C130.0358 (12)0.0420 (13)0.0414 (13)0.0036 (10)0.0024 (10)−0.0050 (11)
C140.0316 (11)0.0459 (13)0.0472 (13)0.0030 (10)0.0034 (10)0.0023 (11)
C150.0424 (13)0.0533 (15)0.0428 (13)0.0017 (11)0.0073 (11)−0.0014 (11)
C160.0544 (15)0.0697 (18)0.0444 (14)−0.0022 (14)0.0158 (12)−0.0033 (13)

Geometric parameters (Å, °)

S1—O21.4249 (18)C4—H4A0.9300
S1—O31.4371 (19)C5—C61.370 (3)
S1—C61.724 (2)C5—H50.9300
S1—C91.726 (2)C6—C71.379 (3)
O1—C11.390 (3)C7—C81.342 (3)
O1—H10.8200C7—H70.9300
O4—C161.402 (3)C8—H80.9300
O4—H40.8200C9—C141.373 (3)
N1—C31.343 (3)C9—C101.379 (3)
N1—C21.422 (3)C10—C111.358 (3)
N1—H1C0.892 (10)C10—H100.9300
N2—C121.341 (3)C11—C121.390 (3)
N2—C151.429 (3)C11—H110.9300
N2—H2C0.895 (10)C12—C131.393 (3)
C1—C21.494 (4)C13—C141.356 (3)
C1—H1A0.9700C13—H130.9300
C1—H1B0.9700C14—H140.9300
C2—H2A0.9700C15—C161.481 (3)
C2—H2B0.9700C15—H15A0.9700
C3—C41.389 (3)C15—H15B0.9700
C3—C81.396 (3)C16—H16A0.9700
C4—C51.361 (3)C16—H16B0.9700
O2—S1—O3118.39 (11)C7—C6—S1119.89 (18)
O2—S1—C6108.63 (11)C8—C7—C6120.7 (2)
O3—S1—C6106.71 (11)C8—C7—H7119.7
O2—S1—C9107.72 (11)C6—C7—H7119.7
O3—S1—C9107.12 (11)C7—C8—C3121.0 (2)
C6—S1—C9107.85 (11)C7—C8—H8119.5
C1—O1—H1109.5C3—C8—H8119.5
C16—O4—H4109.5C14—C9—C10119.6 (2)
C3—N1—C2124.2 (2)C14—C9—S1119.16 (18)
C3—N1—H1C114.2 (16)C10—C9—S1121.22 (18)
C2—N1—H1C120.3 (16)C11—C10—C9120.0 (2)
C12—N2—C15123.6 (2)C11—C10—H10120.0
C12—N2—H2C115.9 (15)C9—C10—H10120.0
C15—N2—H2C119.8 (15)C10—C11—C12121.2 (2)
O1—C1—C2112.2 (2)C10—C11—H11119.4
O1—C1—H1A109.2C12—C11—H11119.4
C2—C1—H1A109.2N2—C12—C11119.9 (2)
O1—C1—H1B109.2N2—C12—C13122.2 (2)
C2—C1—H1B109.2C11—C12—C13117.9 (2)
H1A—C1—H1B107.9C14—C13—C12120.7 (2)
N1—C2—C1109.9 (2)C14—C13—H13119.7
N1—C2—H2A109.7C12—C13—H13119.7
C1—C2—H2A109.7C13—C14—C9120.7 (2)
N1—C2—H2B109.7C13—C14—H14119.7
C1—C2—H2B109.7C9—C14—H14119.7
H2A—C2—H2B108.2N2—C15—C16111.2 (2)
N1—C3—C4123.1 (2)N2—C15—H15A109.4
N1—C3—C8119.2 (2)C16—C15—H15A109.4
C4—C3—C8117.7 (2)N2—C15—H15B109.4
C5—C4—C3120.9 (2)C16—C15—H15B109.4
C5—C4—H4A119.6H15A—C15—H15B108.0
C3—C4—H4A119.6O4—C16—C15113.5 (2)
C4—C5—C6120.3 (2)O4—C16—H16A108.9
C4—C5—H5119.8C15—C16—H16A108.9
C6—C5—H5119.8O4—C16—H16B108.9
C5—C6—C7119.4 (2)C15—C16—H16B108.9
C5—C6—S1120.64 (18)H16A—C16—H16B107.7
C3—N1—C2—C1−175.9 (2)O2—S1—C9—C14161.83 (17)
O1—C1—C2—N160.4 (3)O3—S1—C9—C1433.5 (2)
C2—N1—C3—C4−3.1 (3)C6—S1—C9—C14−81.1 (2)
C2—N1—C3—C8176.8 (2)O2—S1—C9—C10−20.3 (2)
N1—C3—C4—C5−179.1 (2)O3—S1—C9—C10−148.70 (18)
C8—C3—C4—C51.0 (3)C6—S1—C9—C1096.8 (2)
C3—C4—C5—C6−0.2 (3)C14—C9—C10—C11−1.3 (3)
C4—C5—C6—C7−0.4 (3)S1—C9—C10—C11−179.14 (18)
C4—C5—C6—S1177.07 (17)C9—C10—C11—C120.9 (3)
O2—S1—C6—C537.3 (2)C15—N2—C12—C11177.4 (2)
O3—S1—C6—C5166.02 (17)C15—N2—C12—C13−2.2 (3)
C9—S1—C6—C5−79.2 (2)C10—C11—C12—N2−179.1 (2)
O2—S1—C6—C7−145.26 (17)C10—C11—C12—C130.5 (3)
O3—S1—C6—C7−16.6 (2)N2—C12—C13—C14178.0 (2)
C9—S1—C6—C798.25 (19)C11—C12—C13—C14−1.6 (3)
C5—C6—C7—C80.0 (3)C12—C13—C14—C91.2 (3)
S1—C6—C7—C8−177.44 (17)C10—C9—C14—C130.3 (3)
C6—C7—C8—C30.9 (3)S1—C9—C14—C13178.15 (17)
N1—C3—C8—C7178.8 (2)C12—N2—C15—C16−166.6 (2)
C4—C3—C8—C7−1.4 (3)N2—C15—C16—O461.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14—H14···O30.932.592.919 (3)101
C10—H10···O20.932.572.915 (3)102
C7—H7···O30.932.472.854 (3)105
O1—H1···O3i0.821.872.683 (3)175
O1—H1···S1i0.822.883.638 (2)154
O4—H4···O2ii0.822.132.945 (3)177
N1—H1C···O4iii0.892 (10)2.185 (11)3.066 (3)169 (2)
N2—H2C···O1iv0.895 (10)2.027 (11)2.917 (3)172 (2)
C10—H10···Cg2v0.932.973.762 (4)144

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2122).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2001). SHELXTL Version 6.12. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Shahsafi, M. A., Meshkatalsadat, M. H. & Parekh, H. (1987). Indian J. Chem.26B, 803–807.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography