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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808016334/is2296sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808016334/is2296Isup2.hkl
Contains datablock I

CCDC reference: 696490

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.145
  • Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

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.

Related literature top

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 top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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.
1-Naphthyl 9H-carbazole-4-sulfonate top
Crystal data top
C22H15NO3SF(000) = 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 = 2.6–25.7°
b = 9.2098 (4) ŵ = 0.21 mm1
c = 26.3865 (10) ÅT = 295 K
V = 3459.7 (2) Å3Block, colourless
Z = 80.20 × 0.16 × 0.14 mm
Data collection top
Bruker Kappa APEXII
diffractometer
4600 independent reflections
Radiation source: fine-focus sealed tube2928 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω and ϕ scansθmax = 29.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.959, Tmax = 0.971k = 125
22287 measured reflectionsl = 3636
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0727P)2 + 0.3846P]
where P = (Fo2 + 2Fc2)/3
4600 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C22H15NO3SV = 3459.7 (2) Å3
Mr = 373.41Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 14.2365 (5) ŵ = 0.21 mm1
b = 9.2098 (4) ÅT = 295 K
c = 26.3865 (10) Å0.20 × 0.16 × 0.14 mm
Data collection top
Bruker Kappa APEXII
diffractometer
4600 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2928 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.971Rint = 0.034
22287 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.144H-atom parameters constrained
S = 1.06Δρmax = 0.33 e Å3
4600 reflectionsΔρmin = 0.31 e Å3
244 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H70.68190.08040.76760.071*
C80.74173 (14)0.0200 (3)0.70142 (9)0.0559 (5)
H80.69500.05790.68070.067*
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)
H201.29030.15370.55130.088*
C211.1879 (2)0.1435 (3)0.60317 (11)0.0749 (8)
H211.21370.21290.62470.090*
C221.10310 (17)0.0774 (2)0.61653 (8)0.0588 (6)
H221.07240.10260.64640.071*
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) top
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, º) top
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—C31.9 (3)C15—C16—C17—C181.5 (3)
S1—C1—C2—C3172.46 (18)C16—C17—C18—N1177.6 (2)
C1—C2—C3—C40.5 (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—C170.6 (3)
C4—C5—C6—C7176.4 (2)C12—C13—C18—C17178.51 (18)
C10—C5—C6—C72.2 (3)C11—C12—C19—N1178.93 (17)
C5—C6—C7—C80.0 (4)C13—C12—C19—N10.1 (2)
C6—C7—C8—C91.6 (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—C1179.92 (19)C12—C19—C20—C210.3 (4)
C6—C5—C10—C92.7 (3)C19—C20—C21—C220.2 (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—C13.1 (3)C20—C21—C22—C110.3 (4)
C2—C1—C10—C9175.26 (19)C17—C18—N1—C19178.3 (2)
S1—C1—C10—C910.6 (3)C13—C18—N1—C191.0 (2)
C2—C1—C10—C53.7 (3)C20—C19—N1—C18178.2 (2)
S1—C1—C10—C5170.45 (14)C12—C19—N1—C180.6 (2)
C22—C11—C12—C190.6 (3)C22—C11—O1—S191.6 (2)
O1—C11—C12—C19177.99 (16)C12—C11—O1—S190.91 (17)
C22—C11—C12—C13179.0 (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—C191.63 (14)
C19—C12—C13—C14177.9 (2)C2—C1—S1—O24.21 (19)
C11—C12—C13—C18178.1 (2)C10—C1—S1—O2178.61 (15)
C19—C12—C13—C180.5 (2)C2—C1—S1—O3128.18 (17)
C18—C13—C14—C150.6 (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—O164.22 (16)
C14—C15—C16—C170.3 (4)
Hydrogen-bond geometry (Å, º) top
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, y1/2, z; (ii) x+1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC22H15NO3S
Mr373.41
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)295
a, b, c (Å)14.2365 (5), 9.2098 (4), 26.3865 (10)
V3)3459.7 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.20 × 0.16 × 0.14
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.959, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
22287, 4600, 2928
Rint0.034
(sin θ/λ)max1)0.683
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.144, 1.06
No. of reflections4600
No. of parameters244
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.31

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
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, y1/2, z; (ii) x+1/2, y+1/2, z+1.
 

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