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Acta Cryst. (2009). E65, o574    [ doi:10.1107/S1600536809005583 ]

9-Butyl-9H-carbazole

L. Chen, W. Cheng, G.-L. Song and H.-J. Zhu

Abstract top

The title compound, C16H17N, is a carbazole derivative that has been designed and synthesized as a potential organic electronic device, such as an OLED. The tricyclic aromatic ring system is essentially planar, the two outer rings making a dihedral angle of 4.8 (1)°. No classical hydrogen bonds are observed in the crystal structure.

Comment top

The title compound, C16H17N, is a carbazole derivative that has been designed and synthesized as a potential organic electronic device, such as OLED (Yang et al., 2004). We report herein the crystal structure of the title compound, (I), which is of interest to us in the field.

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987). The tricyclic aromatic ring system is essentially planar. There are no classical hydrogen bonds observed in the crystal structure.

Related literature top

For typical bond lengths in organic structures, see: Allen et al. (1987); For general background and related structures, see: Yang et al. (2004).

Experimental top

The title compound, (I), was prepared by a method reported in literature (Yang et al., 2004). The crystals were obtained by dissolving (I) (0.2 g) in petroleum ether (b.p. 60–90 °C) (50 ml) and evaporating the solvent slowly at room temperature for about 3 d.

Refinement top

In the absence of significant anomalous dispersion effects, Friedel pairs were averaged. H atoms were positioned geometrically, C—H = 0.93 and 0.97 Å for aromatic and methyl H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C/O), where x = 1.2 for aromatic H and x = 1.5 for other H.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
9-Butyl-9H-carbazole top
Crystal data top
C16H17NF(000) = 480
Mr = 223.31Dx = 1.165 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 5.544 (1) Åθ = 9–13°
b = 11.276 (2) ŵ = 0.07 mm−1
c = 20.369 (4) ÅT = 298 K
V = 1273.4 (4) Å3Needle, colourless
Z = 40.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		1500 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
graphiteθmax = 25.3°, θmin = 2.0°
ω/2θ scansh = 0→6
Absorption correction: ψ scan
(North et al., 1968)		k = 0→13
Tmin = 0.980, Tmax = 0.993l = −24→24
2671 measured reflections3 standard reflections every 200 reflections
1372 independent reflections intensity decay: 1%
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.06P)2 + 0.13P]
where P = (Fo2 + 2Fc2)/3
1372 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.17 e Å−3
0 restraintsΔρmin = −0.14 e Å−3
Crystal data top
C16H17NV = 1273.4 (4) Å3
Mr = 223.31Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.544 (1) ŵ = 0.07 mm−1
b = 11.276 (2) ÅT = 298 K
c = 20.369 (4) Å0.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		1500 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.062
Tmin = 0.980, Tmax = 0.993θmax = 25.3°
2671 measured reflections3 standard reflections every 200 reflections
1372 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.147Δρmax = 0.17 e Å−3
S = 1.00Δρmin = −0.14 e Å−3
1372 reflectionsAbsolute structure: ?
154 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
N0.1136 (6)0.1561 (2)0.16013 (14)0.0639 (8)
C1−0.0693 (11)−0.1920 (4)0.0678 (2)0.1075 (18)
H1A−0.2201−0.22940.07820.161*
H1B0.0570−0.25020.06800.161*
H1C−0.0796−0.15630.02510.161*
C2−0.0144 (8)−0.0965 (3)0.1188 (2)0.0770 (12)
H2A−0.1447−0.03910.11910.092*
H2B−0.0074−0.13290.16190.092*
C30.2163 (8)−0.0341 (3)0.10593 (19)0.0748 (12)
H3A0.20510.00500.06360.090*
H3B0.3441−0.09260.10300.090*
C40.2869 (8)0.0583 (3)0.1576 (2)0.0784 (12)
H4A0.29520.02050.20030.094*
H4B0.44560.08940.14740.094*
C5−0.0714 (7)0.1694 (3)0.20522 (18)0.0642 (9)
C6−0.1348 (8)0.0987 (4)0.25810 (19)0.0764 (12)
H6A−0.05070.02940.26760.092*
C7−0.3244 (11)0.1343 (4)0.2957 (2)0.0937 (15)
H7A−0.36600.08990.33250.112*
C8−0.4570 (10)0.2346 (4)0.2807 (2)0.0953 (15)
H8A−0.58910.25480.30650.114*
C9−0.3964 (8)0.3046 (4)0.2283 (2)0.0810 (12)
H9A−0.48780.37130.21820.097*
C10−0.1954 (7)0.2748 (3)0.18976 (18)0.0620 (9)
C11−0.0777 (7)0.3272 (3)0.13483 (17)0.0621 (9)
C12−0.1083 (9)0.4315 (3)0.0996 (2)0.0741 (12)
H12A−0.23520.48240.10950.089*
C130.0510 (11)0.4591 (3)0.0499 (2)0.0903 (15)
H13A0.03200.52950.02660.108*
C140.2388 (11)0.3834 (4)0.0341 (2)0.0879 (14)
H14A0.34390.40400.00040.105*
C150.2736 (9)0.2782 (3)0.06719 (19)0.0759 (11)
H15A0.39810.22690.05590.091*
C160.1142 (7)0.2517 (3)0.11837 (18)0.0621 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0568 (19)0.0591 (15)0.0759 (19)0.0061 (15)−0.0073 (18)0.0044 (14)
C10.124 (5)0.098 (3)0.100 (3)−0.004 (4)−0.009 (4)−0.027 (3)
C20.069 (3)0.083 (2)0.079 (3)−0.001 (2)0.012 (3)−0.003 (2)
C30.072 (3)0.069 (2)0.083 (3)0.009 (2)0.005 (2)0.002 (2)
C40.071 (3)0.068 (2)0.097 (3)0.016 (2)−0.007 (3)0.003 (2)
C50.067 (2)0.0624 (19)0.063 (2)−0.0042 (19)−0.008 (2)−0.0021 (17)
C60.074 (3)0.086 (3)0.070 (2)−0.010 (2)−0.007 (3)0.005 (2)
C70.106 (4)0.102 (3)0.073 (3)−0.017 (3)0.011 (3)−0.005 (2)
C80.090 (4)0.117 (3)0.079 (3)−0.015 (3)0.015 (3)−0.035 (3)
C90.069 (3)0.087 (3)0.087 (3)0.003 (2)−0.004 (3)−0.018 (2)
C100.061 (2)0.066 (2)0.059 (2)0.0000 (18)−0.002 (2)−0.0108 (17)
C110.062 (2)0.0638 (18)0.060 (2)−0.002 (2)−0.009 (2)−0.0041 (16)
C120.082 (3)0.061 (2)0.080 (3)0.010 (2)−0.017 (3)−0.0081 (19)
C130.120 (4)0.069 (2)0.081 (3)−0.006 (3)−0.017 (3)0.005 (2)
C140.100 (4)0.091 (3)0.072 (3)−0.017 (3)0.004 (3)0.008 (2)
C150.070 (3)0.077 (2)0.081 (3)−0.006 (2)0.010 (2)−0.002 (2)
C160.061 (2)0.0595 (17)0.066 (2)0.0048 (19)−0.004 (2)−0.0030 (17)
Geometric parameters (Å, °) top
N—C161.373 (4)C6—H6A0.9300
N—C51.385 (4)C7—C81.384 (6)
N—C41.463 (4)C7—H7A0.9300
C1—C21.527 (5)C8—C91.369 (5)
C1—H1A0.9600C8—H8A0.9300
C1—H1B0.9600C9—C101.403 (5)
C1—H1C0.9600C9—H9A0.9300
C2—C31.483 (6)C10—C111.423 (5)
C2—H2A0.9700C11—C121.388 (4)
C2—H2B0.9700C11—C161.403 (5)
C3—C41.532 (5)C12—C131.380 (6)
C3—H3A0.9700C12—H12A0.9300
C3—H3B0.9700C13—C141.384 (6)
C4—H4A0.9700C13—H13A0.9300
C4—H4B0.9700C14—C151.378 (5)
C5—C61.385 (5)C14—H14A0.9300
C5—C101.409 (4)C15—C161.399 (5)
C6—C71.361 (6)C15—H15A0.9300
C16—N—C5109.1 (3)C5—C6—H6A121.2
C16—N—C4124.6 (3)C6—C7—C8121.8 (4)
C5—N—C4126.2 (3)C6—C7—H7A119.1
C2—C1—H1A109.5C8—C7—H7A119.1
C2—C1—H1B109.5C9—C8—C7120.9 (5)
H1A—C1—H1B109.5C9—C8—H8A119.6
C2—C1—H1C109.5C7—C8—H8A119.6
H1A—C1—H1C109.5C8—C9—C10119.5 (4)
H1B—C1—H1C109.5C8—C9—H9A120.2
C3—C2—C1112.7 (4)C10—C9—H9A120.2
C3—C2—H2A109.0C9—C10—C5117.7 (4)
C1—C2—H2A109.0C9—C10—C11134.8 (4)
C3—C2—H2B109.0C5—C10—C11107.6 (3)
C1—C2—H2B109.0C12—C11—C16118.9 (4)
H2A—C2—H2B107.8C12—C11—C10134.5 (4)
C2—C3—C4114.9 (4)C16—C11—C10106.5 (3)
C2—C3—H3A108.5C13—C12—C11119.5 (4)
C4—C3—H3A108.5C13—C12—H12A120.3
C2—C3—H3B108.5C11—C12—H12A120.3
C4—C3—H3B108.5C12—C13—C14120.9 (4)
H3A—C3—H3B107.5C12—C13—H13A119.6
N—C4—C3111.6 (3)C14—C13—H13A119.6
N—C4—H4A109.3C15—C14—C13121.5 (4)
C3—C4—H4A109.3C15—C14—H14A119.2
N—C4—H4B109.3C13—C14—H14A119.2
C3—C4—H4B109.3C14—C15—C16117.4 (4)
H4A—C4—H4B108.0C14—C15—H15A121.3
C6—C5—N129.9 (4)C16—C15—H15A121.3
C6—C5—C10122.4 (4)N—C16—C15129.1 (4)
N—C5—C10107.7 (3)N—C16—C11109.1 (3)
C7—C6—C5117.7 (4)C15—C16—C11121.8 (3)
C7—C6—H6A121.2
C1—C2—C3—C4−177.0 (3)C9—C10—C11—C123.9 (7)
C16—N—C4—C3−82.4 (4)C5—C10—C11—C12−176.8 (4)
C5—N—C4—C399.4 (4)C9—C10—C11—C16−179.1 (4)
C2—C3—C4—N−64.0 (4)C5—C10—C11—C160.2 (4)
C16—N—C5—C6−176.8 (4)C16—C11—C12—C13−0.6 (5)
C4—N—C5—C61.6 (6)C10—C11—C12—C13176.1 (4)
C16—N—C5—C102.0 (4)C11—C12—C13—C140.8 (6)
C4—N—C5—C10−179.6 (3)C12—C13—C14—C150.1 (7)
N—C5—C6—C7178.7 (4)C13—C14—C15—C16−1.2 (6)
C10—C5—C6—C70.1 (5)C5—N—C16—C15177.2 (4)
C5—C6—C7—C82.6 (6)C4—N—C16—C15−1.2 (6)
C6—C7—C8—C9−2.3 (7)C5—N—C16—C11−1.9 (4)
C7—C8—C9—C10−0.7 (6)C4—N—C16—C11179.7 (3)
C8—C9—C10—C53.2 (5)C14—C15—C16—N−177.5 (4)
C8—C9—C10—C11−177.5 (4)C14—C15—C16—C111.5 (5)
C6—C5—C10—C9−3.0 (5)C12—C11—C16—N178.6 (3)
N—C5—C10—C9178.1 (3)C10—C11—C16—N1.0 (4)
C6—C5—C10—C11177.6 (3)C12—C11—C16—C15−0.6 (5)
N—C5—C10—C11−1.3 (4)C10—C11—C16—C15−178.1 (3)
Acknowledgements top

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

references
References top

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