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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1208.
Published online 2008 June 7. doi:  10.1107/S1600536808016334
PMCID: PMC2961653

1-Naphthyl 9H-carbazole-4-sulfonate

Abstract

In the title compound, C22H15NO3S, the plane of the carbazole ring system forms a dihedral angle of 65.06 (4)° with the naphthalene ring system. In the crystal structure, a weak intra­molecular C—H(...)O inter­action is observed between the naphthalene ring system and the sulfonate group. Two weak inter­molecular C—H(...)O inter­actions are also observed.

Related literature

For biological activity, see: Itoigawa et al. (2000 [triangle]); Tachibana et al. (2001 [triangle]). For the structure of closely related compounds, see: Manivannan et al. (2005 [triangle]); Hosomi et al. (2000 [triangle]).

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Object name is e-64-o1208-scheme1.jpg

Experimental

Crystal data

  • C22H15NO3S
  • M r = 373.41
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1208-efi1.jpg
  • a = 14.2365 (5) Å
  • b = 9.2098 (4) Å
  • c = 26.3865 (10) Å
  • V = 3459.7 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.21 mm−1
  • T = 295 (2) K
  • 0.20 × 0.16 × 0.14 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.959, T max = 0.971
  • 22287 measured reflections
  • 4600 independent reflections
  • 2928 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.144
  • S = 1.05
  • 4600 reflections
  • 244 parameters
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: APEX2; 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/S1600536808016334/is2296sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016334/is2296Isup2.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

Carbazole derivatives possess various biological activities, such as antitumor (Itoigawa et al., 2000), antioxidative (Tachibana et al., 2001). We report the crystal structure of the title compound, (I). The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported structures (Manivannan et al., 2005; Hosomi et al., 2000).

The plane of the carbazole ring forms a dihedral angle of 65.06 (4)° with the naphthalene ring. The torsion angles C2—C1—S1—O2 and C10—C1—S1—O3 [4.21 (19) ° and 46.22 (18)°, respectively] indicate a syn conformation of sulfonyl moiety. The molecular structure is stabilized by a weak intramolecular C—H···O interaction and the crystal packing is stabilized by weak intermolecular C—H···O interactions.

Experimental

1-Naphthalene sulfonyl chloride (1.19 g, 5.2 mmol) dissolved in methelene dichloride was slowly added to 9H carbazol-4-ol (0.9 g, 4.8 mmol), followed by the addition of triethylamine (0.72 g, 7 mmol) at 20 °C. The reaction mixture was warmed at 40 °C and maintained at that temperature for 4 h. The reaction mixture was cooled to 15 °C. and mixed with 10 ml of methelene dichloride and 10 ml of water. The methelene dichloride layer was separated, washed to neutral pH with 5% aqueous sodium dicarbonate solution, dried over anhydrous sodium sulfate and concentrated. The crude compound was recrystallized from toluene.

Refinement

H atoms were positioned geometrically (C—H = 0.93 and N—H = 0.86 Å) and refined using riding model, with Uiso(H) = 1.2Ueq(C,N).

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

C22H15NO3SF000 = 1552
Mr = 373.41Dx = 1.434 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4996 reflections
a = 14.2365 (5) Åθ = 2.6–25.7º
b = 9.2098 (4) ŵ = 0.21 mm1
c = 26.3865 (10) ÅT = 295 (2) K
V = 3459.7 (2) Å3Block, colourless
Z = 80.20 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII diffractometer4600 independent reflections
Radiation source: fine-focus sealed tube2928 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.034
T = 295(2) Kθmax = 29.0º
ω and [var phi] scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −19→19
Tmin = 0.959, Tmax = 0.971k = −12→5
22287 measured reflectionsl = −36→36

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.144  w = 1/[σ2(Fo2) + (0.0727P)2 + 0.3846P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
4600 reflectionsΔρmax = 0.33 e Å3
244 parametersΔρmin = −0.31 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
C10.97004 (12)0.1799 (2)0.69244 (7)0.0401 (4)
C21.04048 (14)0.2223 (2)0.72412 (9)0.0533 (5)
H21.09340.26810.71110.064*
C31.03320 (16)0.1971 (3)0.77633 (9)0.0604 (6)
H31.08170.22550.79780.072*
C40.95682 (15)0.1322 (2)0.79553 (8)0.0534 (5)
H40.95270.11770.83030.064*
C50.88229 (13)0.0854 (2)0.76414 (7)0.0422 (4)
C60.80228 (14)0.0161 (2)0.78423 (8)0.0515 (5)
H60.79640.00550.81910.062*
C70.73420 (15)−0.0349 (3)0.75369 (8)0.0593 (6)
H70.6819−0.08040.76760.071*
C80.74173 (14)−0.0200 (3)0.70142 (9)0.0559 (5)
H80.6950−0.05790.68070.067*
C90.81644 (13)0.0493 (2)0.68008 (7)0.0463 (5)
H90.81970.05950.64510.056*
C100.88882 (11)0.1055 (2)0.71077 (6)0.0380 (4)
C111.06625 (13)0.0248 (2)0.58490 (7)0.0427 (4)
C121.10910 (12)0.0642 (2)0.53991 (7)0.0399 (4)
C131.08949 (12)0.1663 (2)0.49984 (6)0.0410 (4)
C141.01942 (14)0.2671 (2)0.49088 (7)0.0484 (5)
H140.96900.27560.51310.058*
C151.02502 (17)0.3552 (3)0.44849 (8)0.0625 (6)
H150.97860.42400.44230.075*
C161.0999 (2)0.3407 (3)0.41514 (8)0.0716 (7)
H161.10270.40110.38690.086*
C171.16910 (19)0.2414 (3)0.42234 (8)0.0677 (7)
H171.21800.23170.39920.081*
C181.16462 (14)0.1546 (3)0.46542 (7)0.0520 (5)
C191.19433 (14)−0.0056 (3)0.52798 (8)0.0541 (5)
C201.23384 (18)−0.1090 (3)0.55964 (10)0.0730 (8)
H201.2903−0.15370.55130.088*
C211.1879 (2)−0.1435 (3)0.60317 (11)0.0749 (8)
H211.2137−0.21290.62470.090*
C221.10310 (17)−0.0774 (2)0.61653 (8)0.0588 (6)
H221.0724−0.10260.64640.071*
N11.22599 (12)0.0506 (2)0.48255 (7)0.0658 (6)
H11.27660.02440.46730.079*
O10.97919 (8)0.08998 (15)0.59681 (5)0.0457 (3)
O21.06505 (11)0.30915 (17)0.62191 (5)0.0598 (4)
O30.89333 (11)0.30371 (18)0.61460 (6)0.0626 (4)
S10.97877 (3)0.23577 (6)0.628849 (18)0.04546 (16)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0447 (9)0.0339 (10)0.0415 (9)−0.0010 (8)0.0063 (7)−0.0057 (7)
C20.0490 (11)0.0476 (13)0.0633 (12)−0.0106 (9)0.0029 (9)−0.0084 (10)
C30.0636 (13)0.0608 (16)0.0568 (12)−0.0069 (11)−0.0150 (10)−0.0117 (11)
C40.0691 (13)0.0501 (13)0.0410 (10)0.0017 (11)−0.0053 (9)−0.0041 (9)
C50.0507 (10)0.0343 (11)0.0415 (9)0.0051 (8)0.0033 (8)0.0004 (7)
C60.0607 (12)0.0488 (13)0.0452 (10)0.0043 (10)0.0121 (9)0.0085 (9)
C70.0482 (12)0.0624 (16)0.0674 (14)−0.0075 (10)0.0138 (10)0.0132 (11)
C80.0442 (11)0.0612 (15)0.0624 (12)−0.0120 (10)−0.0029 (9)0.0051 (10)
C90.0447 (10)0.0512 (13)0.0432 (10)−0.0032 (9)0.0001 (8)0.0022 (8)
C100.0389 (9)0.0338 (10)0.0414 (9)0.0029 (8)0.0046 (7)−0.0014 (7)
C110.0463 (10)0.0393 (11)0.0426 (9)−0.0011 (8)−0.0025 (8)−0.0088 (8)
C120.0386 (9)0.0385 (11)0.0425 (9)−0.0004 (8)−0.0005 (7)−0.0118 (8)
C130.0425 (9)0.0443 (12)0.0362 (8)−0.0069 (8)0.0027 (7)−0.0110 (8)
C140.0557 (11)0.0483 (13)0.0411 (10)−0.0015 (10)0.0005 (8)−0.0048 (8)
C150.0870 (17)0.0538 (15)0.0466 (11)−0.0035 (12)−0.0115 (11)−0.0014 (10)
C160.106 (2)0.0670 (18)0.0423 (11)−0.0281 (16)0.0004 (12)−0.0027 (11)
C170.0813 (16)0.0796 (19)0.0423 (11)−0.0303 (15)0.0199 (11)−0.0164 (11)
C180.0510 (11)0.0589 (14)0.0462 (10)−0.0113 (10)0.0086 (8)−0.0190 (9)
C190.0454 (11)0.0576 (14)0.0594 (12)0.0075 (10)−0.0022 (9)−0.0221 (10)
C200.0644 (15)0.0709 (18)0.0836 (17)0.0301 (13)−0.0190 (13)−0.0302 (14)
C210.0970 (19)0.0535 (16)0.0741 (16)0.0224 (14)−0.0333 (15)−0.0095 (12)
C220.0841 (16)0.0438 (13)0.0485 (11)0.0015 (11)−0.0115 (10)−0.0025 (9)
N10.0471 (10)0.0849 (16)0.0656 (11)0.0042 (10)0.0176 (8)−0.0262 (10)
O10.0445 (7)0.0488 (9)0.0439 (7)−0.0075 (6)0.0085 (5)−0.0082 (6)
O20.0657 (10)0.0492 (10)0.0646 (9)−0.0207 (8)0.0269 (7)−0.0099 (7)
O30.0674 (10)0.0622 (11)0.0582 (9)0.0180 (8)0.0182 (7)0.0154 (7)
S10.0501 (3)0.0403 (3)0.0459 (3)−0.0033 (2)0.0158 (2)−0.0008 (2)

Geometric parameters (Å, °)

C1—C21.363 (3)C12—C131.442 (3)
C1—C101.429 (2)C13—C141.383 (3)
C1—S11.7594 (19)C13—C181.407 (2)
C2—C31.401 (3)C14—C151.384 (3)
C2—H20.9300C14—H140.9300
C3—C41.340 (3)C15—C161.388 (3)
C3—H30.9300C15—H150.9300
C4—C51.413 (3)C16—C171.358 (4)
C4—H40.9300C16—H160.9300
C5—C61.409 (3)C17—C181.391 (3)
C5—C101.424 (2)C17—H170.9300
C6—C71.345 (3)C18—N11.373 (3)
C6—H60.9300C19—N11.381 (3)
C7—C81.390 (3)C19—C201.386 (3)
C7—H70.9300C20—C211.359 (4)
C8—C91.362 (3)C20—H200.9300
C8—H80.9300C21—C221.398 (3)
C9—C101.409 (2)C21—H210.9300
C9—H90.9300C22—H220.9300
C11—C221.363 (3)N1—H10.8600
C11—C121.383 (3)O1—S11.5867 (14)
C11—O11.413 (2)O2—S11.4139 (15)
C12—C191.409 (3)O3—S11.4186 (15)
C2—C1—C10121.70 (18)C18—C13—C12106.01 (17)
C2—C1—S1116.71 (15)C13—C14—C15119.3 (2)
C10—C1—S1121.35 (13)C13—C14—H14120.3
C1—C2—C3120.09 (19)C15—C14—H14120.3
C1—C2—H2120.0C14—C15—C16120.0 (2)
C3—C2—H2120.0C14—C15—H15120.0
C4—C3—C2120.4 (2)C16—C15—H15120.0
C4—C3—H3119.8C17—C16—C15122.2 (2)
C2—C3—H3119.8C17—C16—H16118.9
C3—C4—C5121.59 (19)C15—C16—H16118.9
C3—C4—H4119.2C16—C17—C18117.9 (2)
C5—C4—H4119.2C16—C17—H17121.0
C6—C5—C4121.64 (18)C18—C17—H17121.0
C6—C5—C10118.94 (17)N1—C18—C17129.9 (2)
C4—C5—C10119.40 (17)N1—C18—C13108.96 (18)
C7—C6—C5121.01 (19)C17—C18—C13121.2 (2)
C7—C6—H6119.5N1—C19—C20130.4 (2)
C5—C6—H6119.5N1—C19—C12107.7 (2)
C6—C7—C8120.28 (19)C20—C19—C12121.9 (2)
C6—C7—H7119.9C21—C20—C19118.3 (2)
C8—C7—H7119.9C21—C20—H20120.8
C9—C8—C7121.1 (2)C19—C20—H20120.8
C9—C8—H8119.4C20—C21—C22121.8 (2)
C7—C8—H8119.4C20—C21—H21119.1
C8—C9—C10120.37 (18)C22—C21—H21119.1
C8—C9—H9119.8C11—C22—C21118.6 (2)
C10—C9—H9119.8C11—C22—H22120.7
C9—C10—C5118.22 (16)C21—C22—H22120.7
C9—C10—C1125.02 (16)C18—N1—C19109.83 (16)
C5—C10—C1116.75 (16)C18—N1—H1125.1
C22—C11—C12122.49 (19)C19—N1—H1125.1
C22—C11—O1119.68 (18)C11—O1—S1118.79 (11)
C12—C11—O1117.78 (17)O2—S1—O3119.98 (11)
C11—C12—C19116.86 (19)O2—S1—O1109.40 (8)
C11—C12—C13135.65 (17)O3—S1—O1103.61 (9)
C19—C12—C13107.48 (17)O2—S1—C1108.93 (9)
C14—C13—C18119.31 (19)O3—S1—C1108.73 (9)
C14—C13—C12134.63 (16)O1—S1—C1105.14 (8)
C10—C1—C2—C3−1.9 (3)C15—C16—C17—C18−1.5 (3)
S1—C1—C2—C3172.46 (18)C16—C17—C18—N1−177.6 (2)
C1—C2—C3—C4−0.5 (4)C16—C17—C18—C131.6 (3)
C2—C3—C4—C51.0 (4)C14—C13—C18—N1178.73 (17)
C3—C4—C5—C6179.5 (2)C12—C13—C18—N10.9 (2)
C3—C4—C5—C100.9 (3)C14—C13—C18—C17−0.6 (3)
C4—C5—C6—C7−176.4 (2)C12—C13—C18—C17−178.51 (18)
C10—C5—C6—C72.2 (3)C11—C12—C19—N1−178.93 (17)
C5—C6—C7—C80.0 (4)C13—C12—C19—N1−0.1 (2)
C6—C7—C8—C9−1.6 (4)C11—C12—C19—C200.0 (3)
C7—C8—C9—C101.0 (3)C13—C12—C19—C20178.8 (2)
C8—C9—C10—C51.2 (3)N1—C19—C20—C21179.0 (2)
C8—C9—C10—C1−179.92 (19)C12—C19—C20—C210.3 (4)
C6—C5—C10—C9−2.7 (3)C19—C20—C21—C22−0.2 (4)
C4—C5—C10—C9175.89 (18)C12—C11—C22—C210.7 (3)
C6—C5—C10—C1178.26 (17)O1—C11—C22—C21178.11 (18)
C4—C5—C10—C1−3.1 (3)C20—C21—C22—C11−0.3 (4)
C2—C1—C10—C9−175.26 (19)C17—C18—N1—C19178.3 (2)
S1—C1—C10—C910.6 (3)C13—C18—N1—C19−1.0 (2)
C2—C1—C10—C53.7 (3)C20—C19—N1—C18−178.2 (2)
S1—C1—C10—C5−170.45 (14)C12—C19—N1—C180.6 (2)
C22—C11—C12—C19−0.6 (3)C22—C11—O1—S191.6 (2)
O1—C11—C12—C19−177.99 (16)C12—C11—O1—S1−90.91 (17)
C22—C11—C12—C13−179.0 (2)C11—O1—S1—O225.23 (16)
O1—C11—C12—C133.6 (3)C11—O1—S1—O3154.30 (13)
C11—C12—C13—C140.7 (4)C11—O1—S1—C1−91.63 (14)
C19—C12—C13—C14−177.9 (2)C2—C1—S1—O24.21 (19)
C11—C12—C13—C18178.1 (2)C10—C1—S1—O2178.61 (15)
C19—C12—C13—C18−0.5 (2)C2—C1—S1—O3−128.18 (17)
C18—C13—C14—C15−0.6 (3)C10—C1—S1—O346.22 (18)
C12—C13—C14—C15176.6 (2)C2—C1—S1—O1121.38 (16)
C13—C14—C15—C160.8 (3)C10—C1—S1—O1−64.22 (16)
C14—C15—C16—C170.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O20.932.422.835 (3)107
C8—H8···O3i0.932.503.403 (3)164
C17—H17···O3ii0.932.543.364 (3)147

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2296).

References

  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hosomi, H., Ohba, S. & Ito, Y. (2000). Acta Cryst. C56, e144–e146. [PubMed]
  • Itoigawa, M., Kashiwada, Y., Ito, C., Furukawa, H., Tachibana, Y., Bastow, K. F. & Lee, K. H. (2000). J. Nat. Prod.63, 893–897. [PubMed]
  • 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.
  • Tachibana, Y., Kikuzaki, H., Lajis, N. H. & Nakatani, N. (2001). J. Agric. Food Chem.49, 5589–5594. [PubMed]

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