organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aCollege of Chemistry & Bioengineering, Changsha University of Science & Technology, Changsha 410076, People's Republic of China, and bDepartment of Clinical Laboratory, XiangYa Medical College of Central South University, Changsha 410013, People's Republic of China
*Correspondence e-mail: huangpengmian@126.com

(Received 26 June 2009; accepted 29 June 2009; online 4 July 2009)

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[Duan, X. M., Han, J., Chen, L. G., Xu, Y. J. & Li, Y. (2005). Fine Chem. 22, 39-40, 52. ]). For the pharmaceutical properties of N-alkyl carbazoles, see: Buu-Hoï & Royer (1950[Buu-Hoï, N. P. & Royer, R. (1950). J. Org. Chem. 15, 123-130.]).

[Scheme 1]

Experimental

Crystal data
  • C19H14BrN

  • Mr = 336.22

  • Orthorhombic, P n a 21

  • 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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.682, Tmax = 0.755

  • 14426 measured reflections

  • 3441 independent reflections

  • 2801 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1521 Friedel pairs

  • Flack parameter: −0.005 (10)

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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

Computing details top

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

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. H atoms are presented as spheres of arbitrary radius.
9-Benzyl-3-bromo-9H-carbazole top
Crystal data top
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 top
Rigaku Saturn
diffractometer
3441 independent reflections
Radiation source: rotating anode2801 reflections with I > 2σ(I)
Confocal multilayer X-ray optic monochromatorRint = 0.045
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.8°
ω and ϕ scansh = 2323
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 1919
Tmin = 0.682, Tmax = 0.755l = 77
14426 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036 w = 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 mapAbsolute structure parameter: 0.005 (10)
Crystal data top
C19H14BrNV = 1458.7 (4) Å3
Mr = 336.22Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 17.629 (3) ŵ = 2.81 mm1
b = 14.666 (2) ÅT = 113 K
c = 5.6420 (8) Å0.14 × 0.12 × 0.10 mm
Data collection top
Rigaku Saturn
diffractometer
3441 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
2801 reflections with I > 2σ(I)
Tmin = 0.682, Tmax = 0.755Rint = 0.045
14426 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.069Δρmax = 0.95 e Å3
S = 0.98Δρmin = 0.52 e Å3
3441 reflectionsAbsolute structure: Flack (1983), 1521 Friedel pairs
191 parametersAbsolute structure parameter: 0.005 (10)
1 restraint
Special details top

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) top
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)
H20.40490.29180.02060.027*
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)
H80.68480.13030.00130.027*
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)
H100.67940.02150.60100.031*
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)
H13A0.51850.25880.25630.027*
H13B0.60420.22580.22230.027*
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)
H180.57130.56050.24240.040*
C190.56306 (16)0.42221 (19)0.2030 (6)0.0261 (7)
H190.53450.41200.34320.031*
Atomic displacement parameters (Å2) top
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, º) top
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—C120.1 (4)
C7—N1—C1—C60.3 (3)C10—C11—C12—C70.3 (4)
C13—N1—C1—C6168.5 (2)C10—C11—C12—C6178.6 (3)
N1—C1—C2—C3179.9 (3)N1—C7—C12—C11179.0 (2)
C6—C1—C2—C31.1 (4)C8—C7—C12—C110.1 (4)
C1—C2—C3—C40.7 (4)N1—C7—C12—C60.2 (3)
C2—C3—C4—C50.4 (4)C8—C7—C12—C6178.9 (2)
C2—C3—C4—Br1179.5 (2)C5—C6—C12—C111.5 (5)
C3—C4—C5—C60.5 (4)C1—C6—C12—C11178.5 (3)
Br1—C4—C5—C6179.48 (19)C5—C6—C12—C7180.0 (3)
C4—C5—C6—C10.8 (4)C1—C6—C12—C70.0 (3)
C4—C5—C6—C12179.2 (3)C1—N1—C13—C1473.6 (3)
N1—C1—C6—C5179.8 (2)C7—N1—C13—C1492.7 (3)
C2—C1—C6—C51.2 (4)N1—C13—C14—C19141.7 (3)
N1—C1—C6—C120.2 (3)N1—C13—C14—C1539.1 (4)
C2—C1—C6—C12178.9 (2)C19—C14—C15—C161.5 (4)
C1—N1—C7—C8178.7 (3)C13—C14—C15—C16177.7 (3)
C13—N1—C7—C810.7 (4)C14—C15—C16—C170.9 (4)
C1—N1—C7—C120.3 (3)C15—C16—C17—C180.4 (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—C18177.7 (3)
C7—C8—C9—C100.8 (4)C17—C18—C19—C140.9 (4)

Experimental details

Crystal data
Chemical formulaC19H14BrN
Mr336.22
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)113
a, b, c (Å)17.629 (3), 14.666 (2), 5.6420 (8)
V3)1458.7 (4)
Z4
Radiation typeMo Kα
µ (mm1)2.81
Crystal size (mm)0.14 × 0.12 × 0.10
Data collection
DiffractometerRigaku Saturn
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.682, 0.755
No. of measured, independent and
observed [I > 2σ(I)] reflections
14426, 3441, 2801
Rint0.045
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.069, 0.98
No. of reflections3441
No. of parameters191
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.95, 0.52
Absolute structureFlack (1983), 1521 Friedel pairs
Absolute structure parameter0.005 (10)

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

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

References

First citationBuu-Hoï, N. P. & Royer, R. (1950). J. Org. Chem. 15, 123-130.  CrossRef CAS Google Scholar
First citationDuan, X. M., Han, J., Chen, L. G., Xu, Y. J. & Li, Y. (2005). Fine Chem. 22, 39–40, 52.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationRigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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