9-Butyl-9H-carbazole.

The title compound, C(16)H(17)N, 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 = 223.31

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.147

S = 1.00

1372 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −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.

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

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

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

C16H17N	F(000) = 480
Mr = 223.31	Dx = 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

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

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(Fo2) + (0.06P)2 + 0.13P] where P = (Fo2 + 2Fc2)/3
1372 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)