Literature DB >> 21202847

1-Naphthyl 9H-carbazole-4-sulfonate.

R Arulmozhi, Jasmine P Vennila, Sunil Manohar Babu, Helen P Kavitha, V Manivannan.   

Abstract

In the title compound, C(22)H(15)NO(3)S, 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 intra-molecular C-H⋯O inter-action is observed between the naphthalene ring system and the sulfonate group. Two weak inter-molecular C-H⋯O inter-actions are also observed.

Entities:  

Year:  2008        PMID： 21202847      PMCID： PMC2961653          DOI： 10.1107/S1600536808016334

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Experimental

Crystal data

C22H15NO3S M = 373.41 Orthorhombic, 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 ▶) 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 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97. 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
C22H15NO3SF000 = 1552
Mr = 373.41Dx = 1.434 Mg m−3
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 mm−1
c = 26.3865 (10) ÅT = 295 (2) K
V = 3459.7 (2) Å3Block, colourless
Z = 80.20 × 0.16 × 0.14 mm
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 φ 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 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 Å−3
244 parametersΔρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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)
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)
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)
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
Table 1

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) ; (ii) .

  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Antioxidative activity of carbazoles from Murraya koenigii leaves.

Authors:  Y Tachibana; H Kikuzaki; N H Lajis; N Nakatani
Journal:  J Agric Food Chem       Date:  2001-11       Impact factor: 5.279

3.  Antitumor agents. 203. Carbazole alkaloid murrayaquinone A and related synthetic carbazolequinones as cytotoxic agents.

Authors:  M Itoigawa; Y Kashiwada; C Ito; H Furukawa; Y Tachibana; K F Bastow; K H Lee
Journal:  J Nat Prod       Date:  2000-07       Impact factor: 4.050

4.  Charge-transfer complexes of N-methyl-, N-isopropyl-, N-butyl- and N-isobutylcarbazole with 3,5-dinitrobenzoic acid.

Authors:  H Hosomi; S Ohba; Y Ito
Journal:  Acta Crystallogr C       Date:  2000-04-15       Impact factor: 1.172
  4 in total
  1 in total

1.  2,3,4,9-Tetra-hydro-1H-carbazole.

Authors:  S Murugavel; P S Kannan; A Subbiahpandi; T Surendiran; S Balasubramanian
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-26
  1 in total

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