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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1848.
Published online 2008 August 30. doi:  10.1107/S1600536808027396
PMCID: PMC2960515

4-Nitro­phenyl naphthalene-1-sulfonate

Abstract

In the crystal structure of the title compound, C16H11NO5S, the plane of the naphthalene ring system forms a dihedral angle of 63.39 (8)° with the benzene ring. The nitro group makes a dihedral angle of 10.73 (16)° with the benzene ring. Weak intra- and inter­molecular C—H(...)O inter­actions are observed.

Related literature

For related literature, see: Manivannan et al. (2005 [triangle]); Vennila et al. (2008 [triangle]); Yachi et al. (1989 [triangle]).

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Object name is e-64-o1848-scheme1.jpg

Experimental

Crystal data

  • C16H11NO5S
  • M r = 329.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1848-efi1.jpg
  • a = 13.4407 (8) Å
  • b = 6.2990 (3) Å
  • c = 18.2556 (12) Å
  • β = 106.296 (2)°
  • V = 1483.48 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 295 (2) K
  • 0.28 × 0.20 × 0.16 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.935, T max = 0.962
  • 14281 measured reflections
  • 2801 independent reflections
  • 1935 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.160
  • S = 1.08
  • 2801 reflections
  • 208 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: APEX2 and SAINT (Bruker, 2004 [triangle]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027396/is2328sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027396/is2328Isup2.hkl

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

Acknowledgments

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Chennai, for the data collection.

supplementary crystallographic information

Comment

The merging of lipids can be monitored using a derivative of para-toluene sulfonate (Yachi et al., 1989). The geometric parameters of the title molecule, (I) (Fig. 1), agree well with the reported structures (Manivannan et al. 2005; Vennila et al. 2008)

The plane of the benzene ring forms a dihedral angle of 63.39 (8)° with the naphthalene ring system. The torsion angles O2—S1—C7—C8 and O3—S1—C7—C12 [0.1 (3) ° and 45.8 (2)°, respectively] indicate the syn conformation of sulfonyl moiety. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular C—H···O interactions (Fig. 2).

Experimental

1-Naphthalene sulfonyl chloride (2.5 mmol) dissolved in acetone (4 ml) was added dropwise to 4-nitrophenol (2.5 mmol) in aqueous NaOH (4 ml, 5%) with constant shaking. The precipitated compound (1.8 mmol, yield 72%) was recrystallized from ethanol to get diffraction quality pale yellow crystals.

Refinement

H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C16H11NO5SF000 = 680
Mr = 329.32Dx = 1.474 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4818 reflections
a = 13.4407 (8) Åθ = 2.2–25.4º
b = 6.2990 (3) ŵ = 0.24 mm1
c = 18.2556 (12) ÅT = 295 (2) K
β = 106.296 (2)ºBlock, yellow
V = 1483.48 (15) Å30.28 × 0.20 × 0.16 mm
Z = 4

Data collection

Bruker Kappa APEX2 diffractometer2801 independent reflections
Radiation source: fine-focus sealed tube1935 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 295(2) Kθmax = 25.7º
ω and [var phi] scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −16→16
Tmin = 0.935, Tmax = 0.962k = −7→5
14281 measured reflectionsl = −22→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.160  w = 1/[σ2(Fo2) + (0.0801P)2 + 0.4092P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2801 reflectionsΔρmax = 0.25 e Å3
208 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

xyzUiso*/Ueq
S10.54713 (6)0.94373 (13)0.12153 (4)0.0704 (3)
C10.37278 (18)0.7401 (4)0.09748 (13)0.0528 (6)
C20.3303 (2)0.7033 (4)0.15655 (14)0.0598 (6)
H20.33910.80080.19610.072*
C30.2749 (2)0.5218 (4)0.15633 (15)0.0613 (7)
H30.24540.49370.19570.074*
C40.26342 (18)0.3817 (4)0.09726 (14)0.0537 (6)
C50.3065 (2)0.4177 (4)0.03838 (15)0.0654 (7)
H50.29790.3198−0.00100.079*
C60.3621 (2)0.5999 (4)0.03865 (15)0.0673 (7)
H60.39210.6277−0.00050.081*
C70.58144 (18)0.8465 (4)0.21516 (15)0.0576 (6)
C80.6346 (2)0.6587 (5)0.2287 (2)0.0839 (9)
H80.65000.58510.18910.101*
C90.6658 (3)0.5785 (7)0.3043 (4)0.1117 (16)
H90.70320.45250.31470.134*
C100.6415 (3)0.6838 (9)0.3611 (3)0.1157 (15)
H100.66270.62890.41030.139*
C110.5863 (2)0.8702 (6)0.34821 (18)0.0846 (10)
C120.55403 (18)0.9590 (4)0.27417 (14)0.0577 (6)
C130.5581 (4)0.9799 (11)0.4083 (2)0.1245 (18)
H130.57990.92700.45790.149*
C140.5005 (4)1.1579 (11)0.3943 (3)0.137 (2)
H140.48151.22480.43370.165*
C150.4701 (3)1.2404 (7)0.3225 (3)0.1029 (12)
H150.43121.36470.31390.124*
C160.4949 (2)1.1465 (5)0.26351 (18)0.0725 (8)
H160.47251.20670.21510.087*
O10.42304 (14)0.9358 (3)0.09765 (10)0.0644 (5)
O20.58335 (18)0.7992 (4)0.07547 (14)0.1056 (8)
O30.56871 (18)1.1638 (4)0.11968 (12)0.0901 (7)
O40.1795 (2)0.1450 (4)0.15547 (16)0.1094 (9)
O50.1800 (2)0.0787 (4)0.04028 (14)0.0949 (7)
N10.20241 (18)0.1888 (4)0.09722 (15)0.0705 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0768 (5)0.0848 (6)0.0604 (5)−0.0147 (4)0.0373 (4)−0.0034 (3)
C10.0608 (14)0.0552 (14)0.0448 (12)0.0025 (11)0.0187 (10)0.0049 (11)
C20.0746 (16)0.0619 (16)0.0507 (14)0.0009 (12)0.0304 (12)−0.0052 (12)
C30.0741 (16)0.0690 (17)0.0507 (15)0.0013 (13)0.0337 (12)0.0051 (12)
C40.0581 (14)0.0527 (14)0.0511 (14)0.0055 (11)0.0168 (11)0.0068 (11)
C50.0781 (17)0.0737 (18)0.0491 (14)−0.0039 (14)0.0254 (13)−0.0083 (12)
C60.0809 (18)0.085 (2)0.0436 (14)−0.0105 (15)0.0306 (13)−0.0030 (13)
C70.0517 (13)0.0586 (15)0.0676 (16)−0.0013 (12)0.0252 (12)0.0026 (12)
C80.0627 (16)0.0708 (19)0.124 (3)0.0023 (15)0.0362 (18)−0.0020 (19)
C90.065 (2)0.092 (3)0.167 (5)0.0121 (17)0.014 (2)0.057 (3)
C100.080 (2)0.154 (4)0.098 (3)−0.011 (3)0.001 (2)0.056 (3)
C110.0654 (18)0.120 (3)0.0612 (19)−0.0228 (19)0.0052 (14)0.0139 (18)
C120.0504 (13)0.0711 (17)0.0525 (15)−0.0091 (12)0.0158 (11)0.0008 (12)
C130.101 (3)0.224 (6)0.0479 (19)−0.057 (3)0.0186 (19)−0.009 (3)
C140.119 (4)0.214 (6)0.096 (4)−0.058 (4)0.058 (3)−0.076 (4)
C150.095 (2)0.116 (3)0.112 (3)−0.019 (2)0.052 (2)−0.053 (2)
C160.0740 (18)0.0747 (19)0.0751 (19)−0.0021 (15)0.0312 (15)−0.0112 (15)
O10.0746 (12)0.0641 (12)0.0561 (11)−0.0065 (9)0.0206 (9)0.0071 (8)
O20.1001 (16)0.145 (2)0.0946 (16)−0.0191 (15)0.0642 (14)−0.0393 (15)
O30.1088 (17)0.0895 (15)0.0763 (14)−0.0348 (12)0.0328 (12)0.0139 (11)
O40.151 (2)0.0943 (17)0.1024 (19)−0.0314 (15)0.0678 (18)0.0109 (14)
O50.1127 (19)0.0819 (16)0.0837 (17)−0.0223 (12)0.0167 (13)−0.0090 (12)
N10.0763 (15)0.0610 (15)0.0735 (17)0.0015 (11)0.0196 (13)0.0074 (13)

Geometric parameters (Å, °)

S1—O21.415 (2)C8—C91.418 (6)
S1—O31.419 (2)C8—H80.9300
S1—O11.602 (2)C9—C101.346 (6)
S1—C71.751 (3)C9—H90.9300
C1—C61.367 (4)C10—C111.374 (6)
C1—C21.374 (3)C10—H100.9300
C1—O11.405 (3)C11—C121.414 (4)
C2—C31.364 (4)C11—C131.435 (6)
C2—H20.9300C12—C161.406 (4)
C3—C41.368 (4)C13—C141.345 (7)
C3—H30.9300C13—H130.9300
C4—C51.375 (4)C14—C151.361 (7)
C4—N11.466 (3)C14—H140.9300
C5—C61.369 (4)C15—C161.350 (4)
C5—H50.9300C15—H150.9300
C6—H60.9300C16—H160.9300
C7—C81.368 (4)O4—N11.218 (3)
C7—C121.422 (4)O5—N11.215 (3)
O2—S1—O3120.53 (15)C9—C8—H8120.6
O2—S1—O1108.88 (12)C10—C9—C8120.3 (4)
O3—S1—O1103.19 (12)C10—C9—H9119.9
O2—S1—C7108.34 (15)C8—C9—H9119.9
O3—S1—C7111.42 (13)C9—C10—C11121.7 (4)
O1—S1—C7102.92 (10)C9—C10—H10119.1
C6—C1—C2122.2 (2)C11—C10—H10119.1
C6—C1—O1120.9 (2)C10—C11—C12120.5 (4)
C2—C1—O1116.9 (2)C10—C11—C13121.8 (4)
C3—C2—C1119.1 (2)C12—C11—C13117.7 (4)
C3—C2—H2120.5C16—C12—C11118.3 (3)
C1—C2—H2120.5C16—C12—C7124.8 (2)
C2—C3—C4118.9 (2)C11—C12—C7116.9 (3)
C2—C3—H3120.5C14—C13—C11121.1 (4)
C4—C3—H3120.5C14—C13—H13119.5
C3—C4—C5122.1 (2)C11—C13—H13119.5
C3—C4—N1118.3 (2)C13—C14—C15120.3 (4)
C5—C4—N1119.6 (2)C13—C14—H14119.9
C6—C5—C4119.0 (2)C15—C14—H14119.9
C6—C5—H5120.5C16—C15—C14121.7 (4)
C4—C5—H5120.5C16—C15—H15119.1
C1—C6—C5118.8 (2)C14—C15—H15119.1
C1—C6—H6120.6C15—C16—C12120.9 (3)
C5—C6—H6120.6C15—C16—H16119.5
C8—C7—C12121.8 (3)C12—C16—H16119.5
C8—C7—S1117.4 (2)C1—O1—S1119.41 (15)
C12—C7—S1120.8 (2)O5—N1—O4123.7 (3)
C7—C8—C9118.8 (4)O5—N1—C4118.6 (2)
C7—C8—H8120.6O4—N1—C4117.7 (3)
C6—C1—C2—C3−0.5 (4)C13—C11—C12—C16−1.2 (4)
O1—C1—C2—C3175.8 (2)C10—C11—C12—C70.1 (4)
C1—C2—C3—C40.1 (4)C13—C11—C12—C7−179.1 (3)
C2—C3—C4—C50.4 (4)C8—C7—C12—C16−176.5 (3)
C2—C3—C4—N1−179.1 (2)S1—C7—C12—C163.0 (3)
C3—C4—C5—C6−0.3 (4)C8—C7—C12—C111.3 (4)
N1—C4—C5—C6179.1 (2)S1—C7—C12—C11−179.13 (19)
C2—C1—C6—C50.5 (4)C10—C11—C13—C14−177.4 (4)
O1—C1—C6—C5−175.6 (2)C12—C11—C13—C141.8 (6)
C4—C5—C6—C1−0.1 (4)C11—C13—C14—C15−1.7 (7)
O2—S1—C7—C80.1 (3)C13—C14—C15—C160.9 (7)
O3—S1—C7—C8−134.7 (2)C14—C15—C16—C12−0.3 (5)
O1—S1—C7—C8115.3 (2)C11—C12—C16—C150.5 (4)
O2—S1—C7—C12−179.42 (19)C7—C12—C16—C15178.3 (3)
O3—S1—C7—C1245.8 (2)C6—C1—O1—S1−78.7 (3)
O1—S1—C7—C12−64.2 (2)C2—C1—O1—S1104.9 (2)
C12—C7—C8—C9−2.0 (4)O2—S1—O1—C154.4 (2)
S1—C7—C8—C9178.4 (2)O3—S1—O1—C1−176.40 (18)
C7—C8—C9—C101.3 (5)C7—S1—O1—C1−60.4 (2)
C8—C9—C10—C110.1 (6)C3—C4—N1—O5170.0 (3)
C9—C10—C11—C12−0.8 (5)C5—C4—N1—O5−9.4 (4)
C9—C10—C11—C13178.4 (4)C3—C4—N1—O4−12.0 (4)
C10—C11—C12—C16178.0 (3)C5—C4—N1—O4168.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8···O20.932.432.829 (5)106
C16—H16···O30.932.463.058 (4)122
C5—H5···O2i0.932.483.179 (3)132
C15—H15···O4ii0.932.473.340 (5)155

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1/2, y+3/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2328).

References

  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Manivannan, V., Vembu, N., Nallu, M., Sivakumar, K. & Fronczek, F. R. (2005). Acta Cryst. E61, o528–o530.
  • Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Vennila, J. P., Thilagavathi, R., Kavipriya, R., Kavitha, H. P. & Manivannan, V. (2008). Acta Cryst. E64, o1124. [PMC free article] [PubMed]
  • Yachi, K., Sugiyama, Y., Sawada, Y., Iga, T., Ikeda, Y., Toda, G. & Hananon, M. (1989). Biochim. Biophys. Acta, 978, 1–7. [PubMed]

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