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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1452.
Published online 2009 May 29. doi:  10.1107/S160053680901962X
PMCID: PMC2969652

N-(2-Amino­ethyl)-5-(dimethyl­amino)naphthalene-1-sulfonamide

Abstract

In the title compound, C14H19N3O2S, the N atom of the dimethyl­amino group and the S atom are displaced by 0.078 (2) and 0.084 (2) Å, respectively, from the naphthalene ring plane. The 2-amino­ethyl group has a coiled conformation with an N—C—C—NH2 torsion angle of 53.6 (4)°. In the crystal structure, inter­molecular N—H(...)N and weak C—H(...)O hydrogen bonds link mol­ecules into chains along [001].

Related literature

For applications of ligands containing the 5-(dimethyl­amino)naphthalene-1-sulfonyl (dans­yl) group, see: Corradini et al. (1996 [triangle], 1997 [triangle]); Christoforou et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1452-scheme1.jpg

Experimental

Crystal data

  • C14H19N3O2S
  • M r = 293.38
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1452-efi1.jpg
  • a = 15.5221 (15) Å
  • b = 11.5423 (11) Å
  • c = 8.1360 (8) Å
  • V = 1457.7 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 298 K
  • 0.20 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997 [triangle]) T min = 0.956, T max = 0.956
  • 7478 measured reflections
  • 3140 independent reflections
  • 3012 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.107
  • S = 1.11
  • 3140 reflections
  • 192 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.25 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1332 Friedel pairs
  • Flack parameter: −0.03 (8)

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT-Plus (Bruker, 2007 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901962X/lh2821sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901962X/lh2821Isup2.hkl

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

supplementary crystallographic information

Comment

The dansyl (5-(dimethylamino)naphthalene-1-sulfonyl) group has been widely used as a fluorophore in the design of fluorescent probes. Recently many fluorescent ligands bearing dansyl group have been reported (Corradini et al., 1996,1997; Christoforou et al., 2006). We are interested in preparing fluorescent ligands that are expected to bind to hydrophobic sites in proteins or membranes. With this mind, the title compound, (I), was prepared and we report the crystal stucture herein.

In the molecule (Fig. 1), atoms N1 and S1 are located approximately in the naphthalene ring plane with their deviations being 0.078 and 0.084 Å, respectively. The N2—C14—C15—N3 torsion angle of -53.6 (4)° indicates a coiled conformation for the aminoethyl group. In the crystal structure (Fig.2), intermolecular N—H···N and weak C-H···O hydrogen bonds link molecules into one-dimensional chains along [001].

Experimental

Compound (I) was synthesized according to a literature procedure (Corradini et al., 1996). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a dichloromethane solution of (I) at room temperature.

Refinement

All carbon bound H atoms were placed in their idealized positions [CH(methyl)=0.96 Å and C—H(aromatic) =0.93 Å] and included in the refinement in the riding-model approximation, with Uiso(methyl H)= 1.5Ueq(C) and Uiso(aromatic H) = 1.2Ueq(C). Hydrogen atoms bonded to nitrogen atoms were found in the difference Fourier maps and refined with the constraints of N—H = 0.869(Å) and Uiso(H) = 1.2Ueq(N).

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
Fig. 2.
Part of the crystal structure of (I) showing weak hydrogen bonds as dashed lines. Only H atoms involved in hydrogen bonds are shown.

Crystal data

C14H19N3O2SF(000) = 624
Mr = 293.38Dx = 1.337 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 4085 reflections
a = 15.5221 (15) Åθ = 2.2–28.0°
b = 11.5423 (11) ŵ = 0.23 mm1
c = 8.1360 (8) ÅT = 298 K
V = 1457.7 (2) Å3Block, colorless
Z = 40.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer3140 independent reflections
Radiation source: fine-focus sealed tube3012 reflections with I > 2σ(I)
graphiteRint = 0.029
[var phi] and ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)h = −19→13
Tmin = 0.956, Tmax = 0.956k = −14→14
7478 measured reflectionsl = −10→10

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107w = 1/[σ2(Fo2) + (0.0621P)2 + 0.0989P] where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
3140 reflectionsΔρmax = 0.24 e Å3
192 parametersΔρmin = −0.25 e Å3
1 restraintAbsolute structure: Flack (1983), 1332 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.03 (8)

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
C10.6783 (2)0.2592 (3)1.2600 (5)0.0711 (9)
H1A0.61950.26201.22360.107*
H1B0.67970.25191.37750.107*
H1C0.70650.19371.21110.107*
C20.67195 (17)0.4676 (3)1.2579 (4)0.0615 (7)
H2A0.70300.53681.23000.092*
H2B0.66160.46591.37420.092*
H2C0.61800.46651.20040.092*
C30.75553 (12)0.36601 (19)1.0498 (3)0.0381 (5)
C40.72410 (14)0.43583 (19)0.9255 (3)0.0451 (5)
H40.67960.48740.94770.054*
C50.75833 (15)0.4299 (2)0.7670 (3)0.0480 (6)
H50.73500.47670.68530.058*
C60.82454 (15)0.3580 (2)0.7281 (3)0.0445 (5)
H60.84510.35470.62080.053*
C70.86251 (12)0.28748 (17)0.8530 (3)0.0323 (4)
C80.93538 (13)0.21356 (16)0.8264 (3)0.0309 (4)
C90.96977 (14)0.14947 (18)0.9519 (3)0.0366 (4)
H91.01580.09990.93110.044*
C100.93643 (14)0.15783 (18)1.1106 (3)0.0379 (4)
H100.96100.11511.19540.045*
C110.86816 (12)0.22823 (16)1.1418 (3)0.0363 (4)
H110.84730.23451.24860.044*
C120.82814 (12)0.29230 (16)1.0143 (3)0.0322 (4)
C141.10343 (19)0.3731 (3)0.6827 (4)0.0689 (9)
H14A1.13540.42250.60800.083*
H14B1.14000.30790.71070.083*
C151.0839 (2)0.4406 (3)0.8375 (5)0.0833 (11)
H15A1.06090.38740.91880.100*
H15B1.13750.47120.88050.100*
N10.72278 (13)0.36630 (17)1.2108 (3)0.0467 (5)
O10.92413 (13)0.18510 (17)0.5084 (2)0.0558 (5)
O21.05529 (12)0.12231 (15)0.6510 (2)0.0553 (4)
N21.02722 (14)0.33007 (18)0.5987 (3)0.0495 (5)
H2D1.0054 (19)0.358 (3)0.508 (5)0.059*
N31.0237 (3)0.5358 (3)0.8182 (5)0.0993 (13)
H3A0.980 (3)0.499 (5)0.773 (8)0.119*
H3B1.044 (3)0.588 (4)0.752 (7)0.119*
S10.98740 (3)0.20448 (4)0.63277 (8)0.03840 (15)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0693 (17)0.0655 (18)0.079 (2)0.0010 (15)0.0311 (15)0.0156 (17)
C20.0547 (14)0.0663 (17)0.0635 (18)0.0210 (13)0.0108 (12)−0.0083 (14)
C30.0340 (10)0.0365 (11)0.0439 (12)0.0001 (8)−0.0005 (9)−0.0006 (9)
C40.0377 (10)0.0406 (12)0.0570 (14)0.0071 (9)−0.0008 (10)0.0082 (11)
C50.0472 (12)0.0486 (13)0.0482 (14)0.0062 (10)−0.0097 (10)0.0171 (11)
C60.0533 (12)0.0461 (12)0.0343 (11)−0.0003 (10)−0.0053 (9)0.0120 (10)
C70.0331 (9)0.0315 (9)0.0323 (10)−0.0037 (7)−0.0041 (8)0.0023 (8)
C80.0369 (10)0.0294 (9)0.0264 (10)−0.0018 (8)0.0014 (8)−0.0008 (8)
C90.0418 (10)0.0344 (11)0.0336 (10)0.0061 (8)−0.0015 (9)0.0015 (8)
C100.0450 (10)0.0387 (10)0.0299 (11)0.0066 (8)−0.0045 (8)0.0077 (8)
C110.0434 (10)0.0367 (9)0.0286 (9)0.0018 (7)0.0003 (9)0.0037 (9)
C120.0328 (9)0.0303 (10)0.0335 (10)−0.0049 (7)−0.0015 (8)0.0030 (8)
C140.0647 (16)0.0609 (16)0.081 (3)−0.0208 (14)0.0173 (15)−0.0189 (15)
C150.099 (2)0.077 (2)0.075 (2)−0.034 (2)0.012 (2)−0.0264 (19)
N10.0462 (10)0.0458 (11)0.0482 (11)0.0089 (9)0.0133 (9)0.0015 (9)
O10.0778 (12)0.0595 (11)0.0302 (8)−0.0089 (9)−0.0003 (8)−0.0045 (8)
O20.0729 (10)0.0498 (9)0.0432 (9)0.0162 (8)0.0174 (9)−0.0028 (8)
N20.0641 (13)0.0425 (10)0.0420 (14)−0.0092 (9)0.0122 (9)0.0037 (9)
N30.158 (4)0.0527 (18)0.087 (2)−0.0261 (19)0.036 (2)−0.0248 (16)
S10.0538 (3)0.0341 (2)0.0274 (2)−0.00129 (19)0.0066 (3)−0.0034 (3)

Geometric parameters (Å, °)

C1—N11.472 (3)C8—S11.773 (2)
C1—H1A0.9600C9—C101.395 (3)
C1—H1B0.9600C9—H90.9300
C1—H1C0.9600C10—C111.359 (3)
C2—N11.461 (3)C10—H100.9300
C2—H2A0.9600C11—C121.417 (3)
C2—H2B0.9600C11—H110.9300
C2—H2C0.9600C14—N21.454 (4)
C3—C41.382 (3)C14—C151.511 (5)
C3—N11.405 (3)C14—H14A0.9700
C3—C121.441 (3)C14—H14B0.9700
C4—C51.396 (3)C15—N31.450 (5)
C4—H40.9300C15—H15A0.9700
C5—C61.358 (3)C15—H15B0.9700
C5—H50.9300O1—S11.4278 (19)
C6—C71.429 (3)O2—S11.4255 (18)
C6—H60.9300N2—S11.600 (2)
C7—C121.417 (3)N2—H2D0.87 (3)
C7—C81.433 (3)N3—H3A0.88 (5)
C8—C91.369 (3)N3—H3B0.87 (5)
N1—C1—H1A109.5C9—C10—H10119.9
N1—C1—H1B109.5C10—C11—C12121.1 (2)
H1A—C1—H1B109.5C10—C11—H11119.4
N1—C1—H1C109.5C12—C11—H11119.4
H1A—C1—H1C109.5C11—C12—C7119.47 (18)
H1B—C1—H1C109.5C11—C12—C3120.3 (2)
N1—C2—H2A109.5C7—C12—C3120.20 (18)
N1—C2—H2B109.5N2—C14—C15113.9 (3)
H2A—C2—H2B109.5N2—C14—H14A108.8
N1—C2—H2C109.5C15—C14—H14A108.8
H2A—C2—H2C109.5N2—C14—H14B108.8
H2B—C2—H2C109.5C15—C14—H14B108.8
C4—C3—N1123.6 (2)H14A—C14—H14B107.7
C4—C3—C12118.3 (2)N3—C15—C14115.5 (3)
N1—C3—C12118.11 (19)N3—C15—H15A108.4
C3—C4—C5120.8 (2)C14—C15—H15A108.4
C3—C4—H4119.6N3—C15—H15B108.4
C5—C4—H4119.6C14—C15—H15B108.4
C6—C5—C4122.3 (2)H15A—C15—H15B107.5
C6—C5—H5118.9C3—N1—C2116.2 (2)
C4—C5—H5118.9C3—N1—C1114.9 (2)
C5—C6—C7119.6 (2)C2—N1—C1110.3 (2)
C5—C6—H6120.2C14—N2—S1122.8 (2)
C7—C6—H6120.2C14—N2—H2D126 (2)
C12—C7—C6118.73 (19)S1—N2—H2D109 (2)
C12—C7—C8117.42 (17)C15—N3—H3A100 (3)
C6—C7—C8123.8 (2)C15—N3—H3B111 (3)
C9—C8—C7121.08 (19)H3A—N3—H3B111 (5)
C9—C8—S1116.94 (16)O2—S1—O1118.56 (12)
C7—C8—S1121.94 (15)O2—S1—N2109.58 (12)
C8—C9—C10120.57 (19)O1—S1—N2106.55 (12)
C8—C9—H9119.7O2—S1—C8106.46 (10)
C10—C9—H9119.7O1—S1—C8109.01 (10)
C11—C10—C9120.2 (2)N2—S1—C8106.04 (10)
C11—C10—H10119.9
N1—C3—C4—C5−178.7 (2)C4—C3—C12—C11173.49 (19)
C12—C3—C4—C53.9 (3)N1—C3—C12—C11−4.0 (3)
C3—C4—C5—C6−1.4 (4)C4—C3—C12—C7−3.6 (3)
C4—C5—C6—C7−1.5 (4)N1—C3—C12—C7178.89 (18)
C5—C6—C7—C121.7 (3)N2—C14—C15—N3−53.6 (4)
C5—C6—C7—C8−176.60 (19)C4—C3—N1—C2−18.4 (3)
C12—C7—C8—C90.6 (3)C12—C3—N1—C2159.0 (2)
C6—C7—C8—C9178.9 (2)C4—C3—N1—C1112.6 (3)
C12—C7—C8—S1−177.20 (14)C12—C3—N1—C1−70.0 (3)
C6—C7—C8—S11.1 (3)C15—C14—N2—S1−91.9 (3)
C7—C8—C9—C10−2.3 (3)C14—N2—S1—O2−40.1 (2)
S1—C8—C9—C10175.56 (16)C14—N2—S1—O1−169.58 (19)
C8—C9—C10—C111.3 (3)C14—N2—S1—C874.4 (2)
C9—C10—C11—C121.5 (3)C9—C8—S1—O23.06 (19)
C10—C11—C12—C7−3.2 (3)C7—C8—S1—O2−179.09 (16)
C10—C11—C12—C3179.68 (19)C9—C8—S1—O1132.05 (17)
C6—C7—C12—C11−176.28 (19)C7—C8—S1—O1−50.11 (19)
C8—C7—C12—C112.1 (3)C9—C8—S1—N2−113.59 (18)
C6—C7—C12—C30.8 (3)C7—C8—S1—N264.25 (19)
C8—C7—C12—C3179.24 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···O10.932.483.093 (3)123
N3—H3A···N20.88 (5)2.52 (6)2.972 (4)113 (4)
C11—H11···O1i0.932.493.146 (3)128
N2—H2D···N3ii0.87 (3)2.02 (4)2.869 (4)163 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2821).

References

  • Bruker (2007). SAINT-Plus and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Christoforou, A. M., Marzilli, P. A. & Marzilli, L. G. (2006). Inorg. Chem.45, 6771–6781. [PubMed]
  • Corradini, R., Dossena, A., Galaverna, G., Marchelli, R., Panagia, A. & Sarto, G. (1997). J. Org. Chem.62, 6283–6289.
  • Corradini, R., Dossena, A., Marchelli, R., Panagia, A., Sartor, G., Saviano, M., Lombardi, A. & Pavone, V. (1996). Chem. Eur. J.2, 373–381.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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