9-Butyl-9H-carbazole

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

doi:10.1107/S1600536809005583

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o574

doi:10.1107/S1600536809005583

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9-Butyl-9H-carbazole

Lei Chen,^a Wei Cheng,^a Guang-Liang Song ^a and Hong-Jun Zhu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 16 December 2008; accepted 17 February 2009; online 21 February 2009)

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.

Related literature

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

Experimental

Crystal data

C₁₆H₁₇N
M_r = 223.31
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.544 (1) Å
b = 11.276 (2) Å
c = 20.369 (4) Å
V = 1273.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.980, T_max = 0.993
2671 measured reflections
1372 independent reflections
1500 reflections with I > 2σ(I)
R_int = 0.062
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.147
S = 1.00
1372 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005583/im2093sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809005583/im2093Isup2.hkl

checkCIF report

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.

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

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

C₁₆H₁₇N	F(000) = 480
M_r = 223.31	D_x = 1.165 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 5.544 (1) Å	θ = 9–13°
b = 11.276 (2) Å	µ = 0.07 mm⁻¹
c = 20.369 (4) Å	T = 298 K
V = 1273.4 (4) Å³	Needle, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1500 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.062
Graphite monochromator	θ_max = 25.3°, θ_min = 2.0°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = 0→13
T_min = 0.980, T_max = 0.993	l = −24→24
2671 measured reflections	3 standard reflections every 200 reflections
1372 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.06P)² + 0.13P] where P = (F_o² + 2F_c²)/3
1372 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₆H₁₇N	V = 1273.4 (4) Å³
M_r = 223.31	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.544 (1) Å	µ = 0.07 mm⁻¹
b = 11.276 (2) Å	T = 298 K
c = 20.369 (4) Å	0.30 × 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)	R_int = 0.062
T_min = 0.980, T_max = 0.993	3 standard reflections every 200 reflections
2671 measured reflections	intensity decay: 1%
1372 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.00	Δρ_max = 0.17 e Å⁻³
1372 reflections	Δρ_min = −0.14 e Å⁻³
154 parameters

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

	x	y	z	U_iso*/U_eq
N	0.1136 (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	−0.2294	0.0782	0.161*
H1B	0.0570	−0.2502	0.0680	0.161*
H1C	−0.0796	−0.1563	0.0251	0.161*
C2	−0.0144 (8)	−0.0965 (3)	0.1188 (2)	0.0770 (12)
H2A	−0.1447	−0.0391	0.1191	0.092*
H2B	−0.0074	−0.1329	0.1619	0.092*
C3	0.2163 (8)	−0.0341 (3)	0.10593 (19)	0.0748 (12)
H3A	0.2051	0.0050	0.0636	0.090*
H3B	0.3441	−0.0926	0.1030	0.090*
C4	0.2869 (8)	0.0583 (3)	0.1576 (2)	0.0784 (12)
H4A	0.2952	0.0205	0.2003	0.094*
H4B	0.4456	0.0894	0.1474	0.094*
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	−0.0507	0.0294	0.2676	0.092*
C7	−0.3244 (11)	0.1343 (4)	0.2957 (2)	0.0937 (15)
H7A	−0.3660	0.0899	0.3325	0.112*
C8	−0.4570 (10)	0.2346 (4)	0.2807 (2)	0.0953 (15)
H8A	−0.5891	0.2548	0.3065	0.114*
C9	−0.3964 (8)	0.3046 (4)	0.2283 (2)	0.0810 (12)
H9A	−0.4878	0.3713	0.2182	0.097*
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	−0.2352	0.4824	0.1095	0.089*
C13	0.0510 (11)	0.4591 (3)	0.0499 (2)	0.0903 (15)
H13A	0.0320	0.5295	0.0266	0.108*
C14	0.2388 (11)	0.3834 (4)	0.0341 (2)	0.0879 (14)
H14A	0.3439	0.4040	0.0004	0.105*
C15	0.2736 (9)	0.2782 (3)	0.06719 (19)	0.0759 (11)
H15A	0.3981	0.2269	0.0559	0.091*
C16	0.1142 (7)	0.2517 (3)	0.11837 (18)	0.0621 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0568 (19)	0.0591 (15)	0.0759 (19)	0.0061 (15)	−0.0073 (18)	0.0044 (14)
C1	0.124 (5)	0.098 (3)	0.100 (3)	−0.004 (4)	−0.009 (4)	−0.027 (3)
C2	0.069 (3)	0.083 (2)	0.079 (3)	−0.001 (2)	0.012 (3)	−0.003 (2)
C3	0.072 (3)	0.069 (2)	0.083 (3)	0.009 (2)	0.005 (2)	0.002 (2)
C4	0.071 (3)	0.068 (2)	0.097 (3)	0.016 (2)	−0.007 (3)	0.003 (2)
C5	0.067 (2)	0.0624 (19)	0.063 (2)	−0.0042 (19)	−0.008 (2)	−0.0021 (17)
C6	0.074 (3)	0.086 (3)	0.070 (2)	−0.010 (2)	−0.007 (3)	0.005 (2)
C7	0.106 (4)	0.102 (3)	0.073 (3)	−0.017 (3)	0.011 (3)	−0.005 (2)
C8	0.090 (4)	0.117 (3)	0.079 (3)	−0.015 (3)	0.015 (3)	−0.035 (3)
C9	0.069 (3)	0.087 (3)	0.087 (3)	0.003 (2)	−0.004 (3)	−0.018 (2)
C10	0.061 (2)	0.066 (2)	0.059 (2)	0.0000 (18)	−0.002 (2)	−0.0108 (17)
C11	0.062 (2)	0.0638 (18)	0.060 (2)	−0.002 (2)	−0.009 (2)	−0.0041 (16)
C12	0.082 (3)	0.061 (2)	0.080 (3)	0.010 (2)	−0.017 (3)	−0.0081 (19)
C13	0.120 (4)	0.069 (2)	0.081 (3)	−0.006 (3)	−0.017 (3)	0.005 (2)
C14	0.100 (4)	0.091 (3)	0.072 (3)	−0.017 (3)	0.004 (3)	0.008 (2)
C15	0.070 (3)	0.077 (2)	0.081 (3)	−0.006 (2)	0.010 (2)	−0.002 (2)
C16	0.061 (2)	0.0595 (17)	0.066 (2)	0.0048 (19)	−0.004 (2)	−0.0030 (17)

Geometric parameters (Å, º) top

N—C16	1.373 (4)	C6—H6A	0.9300
N—C5	1.385 (4)	C7—C8	1.384 (6)
N—C4	1.463 (4)	C7—H7A	0.9300
C1—C2	1.527 (5)	C8—C9	1.369 (5)
C1—H1A	0.9600	C8—H8A	0.9300
C1—H1B	0.9600	C9—C10	1.403 (5)
C1—H1C	0.9600	C9—H9A	0.9300
C2—C3	1.483 (6)	C10—C11	1.423 (5)
C2—H2A	0.9700	C11—C12	1.388 (4)
C2—H2B	0.9700	C11—C16	1.403 (5)
C3—C4	1.532 (5)	C12—C13	1.380 (6)
C3—H3A	0.9700	C12—H12A	0.9300
C3—H3B	0.9700	C13—C14	1.384 (6)
C4—H4A	0.9700	C13—H13A	0.9300
C4—H4B	0.9700	C14—C15	1.378 (5)
C5—C6	1.385 (5)	C14—H14A	0.9300
C5—C10	1.409 (4)	C15—C16	1.399 (5)
C6—C7	1.361 (6)	C15—H15A	0.9300

C16—N—C5	109.1 (3)	C5—C6—H6A	121.2
C16—N—C4	124.6 (3)	C6—C7—C8	121.8 (4)
C5—N—C4	126.2 (3)	C6—C7—H7A	119.1
C2—C1—H1A	109.5	C8—C7—H7A	119.1
C2—C1—H1B	109.5	C9—C8—C7	120.9 (5)
H1A—C1—H1B	109.5	C9—C8—H8A	119.6
C2—C1—H1C	109.5	C7—C8—H8A	119.6
H1A—C1—H1C	109.5	C8—C9—C10	119.5 (4)
H1B—C1—H1C	109.5	C8—C9—H9A	120.2
C3—C2—C1	112.7 (4)	C10—C9—H9A	120.2
C3—C2—H2A	109.0	C9—C10—C5	117.7 (4)
C1—C2—H2A	109.0	C9—C10—C11	134.8 (4)
C3—C2—H2B	109.0	C5—C10—C11	107.6 (3)
C1—C2—H2B	109.0	C12—C11—C16	118.9 (4)
H2A—C2—H2B	107.8	C12—C11—C10	134.5 (4)
C2—C3—C4	114.9 (4)	C16—C11—C10	106.5 (3)
C2—C3—H3A	108.5	C13—C12—C11	119.5 (4)
C4—C3—H3A	108.5	C13—C12—H12A	120.3
C2—C3—H3B	108.5	C11—C12—H12A	120.3
C4—C3—H3B	108.5	C12—C13—C14	120.9 (4)
H3A—C3—H3B	107.5	C12—C13—H13A	119.6
N—C4—C3	111.6 (3)	C14—C13—H13A	119.6
N—C4—H4A	109.3	C15—C14—C13	121.5 (4)
C3—C4—H4A	109.3	C15—C14—H14A	119.2
N—C4—H4B	109.3	C13—C14—H14A	119.2
C3—C4—H4B	109.3	C14—C15—C16	117.4 (4)
H4A—C4—H4B	108.0	C14—C15—H15A	121.3
C6—C5—N	129.9 (4)	C16—C15—H15A	121.3
C6—C5—C10	122.4 (4)	N—C16—C15	129.1 (4)
N—C5—C10	107.7 (3)	N—C16—C11	109.1 (3)
C7—C6—C5	117.7 (4)	C15—C16—C11	121.8 (3)
C7—C6—H6A	121.2

C1—C2—C3—C4	−177.0 (3)	C9—C10—C11—C12	3.9 (7)
C16—N—C4—C3	−82.4 (4)	C5—C10—C11—C12	−176.8 (4)
C5—N—C4—C3	99.4 (4)	C9—C10—C11—C16	−179.1 (4)
C2—C3—C4—N	−64.0 (4)	C5—C10—C11—C16	0.2 (4)
C16—N—C5—C6	−176.8 (4)	C16—C11—C12—C13	−0.6 (5)
C4—N—C5—C6	1.6 (6)	C10—C11—C12—C13	176.1 (4)
C16—N—C5—C10	2.0 (4)	C11—C12—C13—C14	0.8 (6)
C4—N—C5—C10	−179.6 (3)	C12—C13—C14—C15	0.1 (7)
N—C5—C6—C7	178.7 (4)	C13—C14—C15—C16	−1.2 (6)
C10—C5—C6—C7	0.1 (5)	C5—N—C16—C15	177.2 (4)
C5—C6—C7—C8	2.6 (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—C11	179.7 (3)
C8—C9—C10—C5	3.2 (5)	C14—C15—C16—N	−177.5 (4)
C8—C9—C10—C11	−177.5 (4)	C14—C15—C16—C11	1.5 (5)
C6—C5—C10—C9	−3.0 (5)	C12—C11—C16—N	178.6 (3)
N—C5—C10—C9	178.1 (3)	C10—C11—C16—N	1.0 (4)
C6—C5—C10—C11	177.6 (3)	C12—C11—C16—C15	−0.6 (5)
N—C5—C10—C11	−1.3 (4)	C10—C11—C16—C15	−178.1 (3)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N
M_r	223.31
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	5.544 (1), 11.276 (2), 20.369 (4)
V (Å³)	1273.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.980, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	2671, 1372, 1500
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.147, 1.00
No. of reflections	1372
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.14

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

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

References

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Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
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