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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1763.
Published online 2009 July 4. doi:  10.1107/S1600536809024969
PMCID: PMC2977497

9-Benzyl-3-bromo-9H-carbazole

Abstract

The title compound, C19H14BrN, was synthesized by the N-alkyl­ation of (chloro­meth­yl)benzene with 3-bromo-9H-carbazole. The carbazole ring system is essentially planar (r.m.s. deviation = 0.013 Å) and forms a dihedral angle of 87.1 (2)° with the phenyl ring.

Related literature

For the synthesis, see: Duan et al. (2005 [triangle]). For the pharmaceutical properties of N-alkyl carbazoles, see: Buu-Hoï & Royer (1950 [triangle]).

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Object name is e-65-o1763-scheme1.jpg

Experimental

Crystal data

  • C19H14BrN
  • M r = 336.22
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1763-efi1.jpg
  • a = 17.629 (3) Å
  • b = 14.666 (2) Å
  • c = 5.6420 (8) Å
  • V = 1458.7 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.81 mm−1
  • T = 113 K
  • 0.14 × 0.12 × 0.10 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.682, T max = 0.755
  • 14426 measured reflections
  • 3441 independent reflections
  • 2801 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.069
  • S = 0.98
  • 3441 reflections
  • 191 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.95 e Å−3
  • Δρmin = −0.52 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1521 Friedel pairs
  • Flack parameter: −0.005 (10)

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024969/hb5016sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024969/hb5016Isup2.hkl

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

Acknowledgments

This work was supported by the Changsha Science and Technology Bureau (k0803061-11) and Scientific Research Foundation of Hunan Provience (S2007F123) .

supplementary crystallographic information

Comment

N-Alkyl carbazoles possess valuable pharmaceutical properties (Buu-Hoï & Royer, 1950). In this paper, the synthesis and the crystal structure of the title compound, (I), is reported.

The carbazole ring is essentially planar, with a r.m.s. deviation from the mean plane of 0.013 Å for the non-hydrogen atoms. The dihedral angle formed between the carbazole unit and the benzene ring is 92.9 (2) Å.

Experimental

The title compound was prepared according to the procedure of Duan et al. (2005). The title compound (40 mg) was dissolved in a mixture of chloroform (5 ml) and ethanol (7 ml) and the solution was kept at room temperature for 11 days. Evaporation of the solution gave colourless blocks of (I).

Refinement

All H atoms were included in idealized positions (C—H = 0.95–0.99Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
Molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. H atoms are presented as spheres of arbitrary radius.

Crystal data

C19H14BrNDx = 1.531 Mg m3
Mr = 336.22Melting point = 392–394 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2c -2nCell parameters from 3798 reflections
a = 17.629 (3) Åθ = 1.8–27.9°
b = 14.666 (2) ŵ = 2.81 mm1
c = 5.6420 (8) ÅT = 113 K
V = 1458.7 (4) Å3Block, colorless
Z = 40.14 × 0.12 × 0.10 mm
F(000) = 680

Data collection

Rigaku Saturn diffractometer3441 independent reflections
Radiation source: rotating anode2801 reflections with I > 2σ(I)
confocal multilayer X-ray opticRint = 0.045
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.8°
ω and [var phi] scansh = −23→23
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −19→19
Tmin = 0.682, Tmax = 0.755l = −7→7
14426 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036w = 1/[σ2(Fo2) + (0.0241P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.069(Δ/σ)max = 0.001
S = 0.98Δρmax = 0.95 e Å3
3441 reflectionsΔρmin = −0.52 e Å3
191 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0148 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1521 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.005 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br10.257493 (13)0.192950 (18)0.66598 (14)0.02943 (11)
N10.53686 (13)0.19508 (14)0.0539 (4)0.0196 (5)
C10.46874 (12)0.20289 (15)0.1699 (6)0.0180 (5)
C20.40547 (16)0.25415 (17)0.1164 (5)0.0229 (7)
H20.40490.2918−0.02060.027*
C30.34289 (16)0.25037 (19)0.2638 (5)0.0231 (7)
H30.29880.28490.22780.028*
C40.34503 (16)0.19535 (18)0.4663 (5)0.0206 (7)
C50.40726 (15)0.14351 (19)0.5264 (5)0.0191 (6)
H50.40720.10640.66430.023*
C60.47028 (15)0.14744 (17)0.3781 (5)0.0176 (6)
C70.58394 (13)0.13641 (16)0.1792 (6)0.0191 (6)
C80.65823 (14)0.10891 (17)0.1344 (6)0.0228 (7)
H80.68480.1303−0.00130.027*
C90.69198 (16)0.0502 (2)0.2913 (5)0.0269 (7)
H90.74240.03030.26170.032*
C100.65424 (18)0.0186 (2)0.4947 (5)0.0260 (7)
H100.6794−0.02150.60100.031*
C110.58048 (16)0.04587 (18)0.5403 (5)0.0222 (7)
H110.55470.02460.67740.027*
C120.54435 (15)0.10506 (18)0.3825 (5)0.0179 (6)
C130.56053 (16)0.25418 (18)−0.1405 (5)0.0224 (7)
H13A0.51850.2588−0.25630.027*
H13B0.60420.2258−0.22230.027*
C140.58274 (15)0.34943 (19)−0.0620 (5)0.0197 (6)
C150.62312 (14)0.36493 (17)0.1461 (6)0.0241 (6)
H150.63600.31540.24700.029*
C160.64439 (15)0.4530 (2)0.2054 (6)0.0307 (8)
H160.67260.46310.34640.037*
C170.6255 (2)0.5257 (2)0.0643 (6)0.0344 (9)
H170.64020.58580.10770.041*
C180.58455 (17)0.5108 (2)−0.1427 (7)0.0336 (8)
H180.57130.5605−0.24240.040*
C190.56306 (16)0.42221 (19)−0.2030 (6)0.0261 (7)
H190.53450.4120−0.34320.031*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.01928 (15)0.03967 (17)0.02934 (18)0.00396 (12)0.0029 (2)−0.0045 (2)
N10.0176 (13)0.0205 (12)0.0208 (13)−0.0014 (10)0.0012 (11)0.0036 (11)
C10.0175 (12)0.0180 (12)0.0184 (14)−0.0031 (10)−0.002 (2)−0.0038 (16)
C20.0249 (15)0.0199 (14)0.024 (2)−0.0015 (12)−0.0055 (13)0.0013 (13)
C30.0202 (16)0.0211 (15)0.0279 (17)0.0034 (13)−0.0056 (13)−0.0036 (13)
C40.0152 (15)0.0237 (16)0.0228 (16)0.0004 (12)0.0026 (13)−0.0038 (13)
C50.0179 (15)0.0189 (14)0.0204 (16)−0.0040 (12)−0.0021 (12)−0.0011 (12)
C60.0166 (15)0.0150 (14)0.0213 (15)−0.0022 (11)−0.0031 (13)−0.0029 (12)
C70.0185 (12)0.0173 (12)0.0214 (14)−0.0035 (10)−0.0027 (18)−0.0048 (16)
C80.0159 (13)0.0259 (14)0.0268 (19)−0.0044 (11)0.0002 (14)−0.0051 (15)
C90.0186 (16)0.0258 (17)0.0364 (19)−0.0017 (13)−0.0015 (15)−0.0078 (15)
C100.0228 (17)0.0225 (15)0.0326 (18)0.0020 (13)−0.0053 (14)0.0002 (14)
C110.0201 (16)0.0231 (15)0.0233 (16)−0.0031 (12)−0.0031 (13)−0.0015 (13)
C120.0178 (15)0.0140 (13)0.0217 (16)−0.0042 (11)0.0010 (13)−0.0034 (12)
C130.0195 (16)0.0267 (16)0.0209 (15)−0.0024 (12)0.0024 (13)0.0004 (14)
C140.0170 (15)0.0208 (14)0.0215 (17)0.0003 (12)0.0076 (13)0.0035 (14)
C150.0272 (14)0.0229 (14)0.0222 (16)−0.0034 (11)0.0000 (18)0.0000 (17)
C160.0311 (16)0.0336 (17)0.028 (2)−0.0080 (13)0.0013 (15)−0.0054 (16)
C170.039 (2)0.0210 (16)0.043 (2)−0.0068 (15)0.0162 (16)−0.0033 (16)
C180.0319 (19)0.0247 (16)0.044 (2)0.0040 (14)0.0113 (18)0.0080 (16)
C190.0213 (16)0.0324 (17)0.0244 (17)0.0004 (13)0.0045 (14)0.0051 (14)

Geometric parameters (Å, °)

Br1—C41.911 (3)C9—H90.9500
N1—C11.373 (3)C10—C111.385 (4)
N1—C71.389 (3)C10—H100.9500
N1—C131.459 (3)C11—C121.397 (4)
C1—C21.379 (3)C11—H110.9500
C1—C61.429 (4)C13—C141.517 (4)
C2—C31.382 (4)C13—H13A0.9900
C2—H20.9500C13—H13B0.9900
C3—C41.399 (4)C14—C191.376 (4)
C3—H30.9500C14—C151.392 (4)
C4—C51.377 (4)C15—C161.385 (4)
C5—C61.392 (4)C15—H150.9500
C5—H50.9500C16—C171.373 (4)
C6—C121.446 (3)C16—H160.9500
C7—C81.393 (3)C17—C181.390 (5)
C7—C121.419 (4)C17—H170.9500
C8—C91.371 (4)C18—C191.395 (4)
C8—H80.9500C18—H180.9500
C9—C101.405 (4)C19—H190.9500
C1—N1—C7109.4 (2)C9—C10—H10120.0
C1—N1—C13124.0 (2)C10—C11—C12119.3 (3)
C7—N1—C13125.4 (2)C10—C11—H11120.4
N1—C1—C2130.5 (3)C12—C11—H11120.4
N1—C1—C6109.1 (2)C11—C12—C7119.5 (2)
C2—C1—C6120.4 (3)C11—C12—C6133.6 (3)
C1—C2—C3119.5 (3)C7—C12—C6106.9 (2)
C1—C2—H2120.3N1—C13—C14113.7 (2)
C3—C2—H2120.3N1—C13—H13A108.8
C2—C3—C4119.5 (3)C14—C13—H13A108.8
C2—C3—H3120.2N1—C13—H13B108.8
C4—C3—H3120.2C14—C13—H13B108.8
C5—C4—C3122.8 (3)H13A—C13—H13B107.7
C5—C4—Br1119.2 (2)C19—C14—C15119.3 (3)
C3—C4—Br1118.1 (2)C19—C14—C13118.7 (3)
C4—C5—C6117.7 (3)C15—C14—C13121.9 (2)
C4—C5—H5121.2C16—C15—C14119.6 (3)
C6—C5—H5121.2C16—C15—H15120.2
C5—C6—C1120.2 (2)C14—C15—H15120.2
C5—C6—C12133.8 (3)C17—C16—C15121.3 (3)
C1—C6—C12106.0 (2)C17—C16—H16119.4
N1—C7—C8130.4 (3)C15—C16—H16119.4
N1—C7—C12108.6 (2)C16—C17—C18119.4 (3)
C8—C7—C12121.0 (3)C16—C17—H17120.3
C9—C8—C7118.2 (3)C18—C17—H17120.3
C9—C8—H8120.9C17—C18—C19119.5 (3)
C7—C8—H8120.9C17—C18—H18120.2
C8—C9—C10121.9 (3)C19—C18—H18120.2
C8—C9—H9119.0C14—C19—C18120.9 (3)
C10—C9—H9119.0C14—C19—H19119.6
C11—C10—C9120.1 (3)C18—C19—H19119.6
C11—C10—H10120.0
C7—N1—C1—C2178.6 (3)C8—C9—C10—C110.7 (4)
C13—N1—C1—C210.5 (4)C9—C10—C11—C12−0.1 (4)
C7—N1—C1—C6−0.3 (3)C10—C11—C12—C7−0.3 (4)
C13—N1—C1—C6−168.5 (2)C10—C11—C12—C6−178.6 (3)
N1—C1—C2—C3−179.9 (3)N1—C7—C12—C11−179.0 (2)
C6—C1—C2—C3−1.1 (4)C8—C7—C12—C110.1 (4)
C1—C2—C3—C40.7 (4)N1—C7—C12—C6−0.2 (3)
C2—C3—C4—C5−0.4 (4)C8—C7—C12—C6178.9 (2)
C2—C3—C4—Br1179.5 (2)C5—C6—C12—C11−1.5 (5)
C3—C4—C5—C60.5 (4)C1—C6—C12—C11178.5 (3)
Br1—C4—C5—C6−179.48 (19)C5—C6—C12—C7180.0 (3)
C4—C5—C6—C1−0.8 (4)C1—C6—C12—C70.0 (3)
C4—C5—C6—C12179.2 (3)C1—N1—C13—C1473.6 (3)
N1—C1—C6—C5−179.8 (2)C7—N1—C13—C14−92.7 (3)
C2—C1—C6—C51.2 (4)N1—C13—C14—C19−141.7 (3)
N1—C1—C6—C120.2 (3)N1—C13—C14—C1539.1 (4)
C2—C1—C6—C12−178.9 (2)C19—C14—C15—C16−1.5 (4)
C1—N1—C7—C8−178.7 (3)C13—C14—C15—C16177.7 (3)
C13—N1—C7—C8−10.7 (4)C14—C15—C16—C170.9 (4)
C1—N1—C7—C120.3 (3)C15—C16—C17—C18−0.4 (5)
C13—N1—C7—C12168.3 (2)C16—C17—C18—C190.3 (5)
N1—C7—C8—C9179.3 (3)C15—C14—C19—C181.5 (4)
C12—C7—C8—C90.4 (4)C13—C14—C19—C18−177.7 (3)
C7—C8—C9—C10−0.8 (4)C17—C18—C19—C14−0.9 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5016).

References

  • Buu-Hoï, N. P. & Royer, R. (1950). J. Org. Chem.15, 123-130.
  • Duan, X. M., Han, J., Chen, L. G., Xu, Y. J. & Li, Y. (2005). Fine Chem.22, 39–40, 52.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Rigaku/MSC (2005). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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