9-(4-Bromo­but­yl)-9H-carbazole

Moreno-Fuquen, R.; Grande, C.; Advincula, R.C.; Tenorio, J.C.; Ellena, J.

doi:10.1107/S1600536812022398

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1853

doi:10.1107/S1600536812022398

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9-(4-Bromobutyl)-9H-carbazole

Rodolfo Moreno-Fuquen,^a ^* Carlos Grande,^b Rigoberto C. Advincula,^c Juan C. Tenorio ^d and Javier Ellena ^d

^aDepartamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, ^bPrograma de Ingenieria Agroindustrial, Universidad San Buenaventura, AA 7154, Santiago de Cali, Colombia, ^cCase Western Reserve University, Department of Macromolecular Science and Engineering, 2100 Adelbert Road, Kent Hale Smith Bldg, Cleveland, Ohio 44106, USA, and ^dInstituto de Física de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
^*Correspondence e-mail: rodimo26@yahoo.es

(Received 18 April 2012; accepted 17 May 2012; online 23 May 2012)

In the title compound, C₁₆H₁₆BrN, the tricyclic carbazole system is essentially planar (r.m.s. deviation of all non-H atoms = 0.010 Å). The dihedral angle between the two outer carbazole rings is 1.1 (3)°. There are no directional intermolecular contacts in the crystal packing.

Related literature

For synthesis and properties of carbazole derivatives, see: Bo et al. (1998 ). For chemical properties of carbazoles, see: Knolker & Reddy (2002 ), for their physical properties, see: Koyuncu et al. (2011 ), for their medicinal properties, see: Zhang et al. (2010 ) and for their opto-electronic and electrochemical properties, see: Taranekar et al. (2007 ); Morisaki et al. (2009 ). For related structures, see: Gerkin & Reppart (1986 ); Duan et al. (2005 ); Zhou et al. (2008 ); Panchatcharam et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₆BrN
M_r = 302.21
Orthorhombic, P b c a
a = 16.0949 (4) Å
b = 7.7012 (2) Å
c = 22.6874 (4) Å
V = 2812.10 (11) Å³
Z = 8
Mo Kα radiation
μ = 2.91 mm⁻¹
T = 293 K
0.24 × 0.21 × 0.17 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.510, T_max = 0.589
25173 measured reflections
2860 independent reflections
2002 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.146
S = 1.03
2860 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812022398/zs2201sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022398/zs2201Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022398/zs2201Isup3.cml

checkCIF report

Comment top

The carbazole ring has a highly conjugated π system with desirable optical and charge-transport properties. These characteristics make it an excellent candidate for applications in different areas of science. Indeed, carbazole and its derivatives, heterocyclic compounds with a N atom in their structure, have interesting chemical (Knolker & Reddy, 2002), physical (Koyuncu et al., 2011) and medicinal (Zhang et al., 2010) properties. Polymers based on carbazole units become promising materials because of their optical, electronic and electrochemical behaviors (Taranekar et al., 2007; Morisaki et al., 2009). One of these derivatives, 9-(4-bromobutyl)-9H-carbazole, the title compound C₁₆H₁₆BrN, was synthesized and its structure is reported here.

In the title compound (Fig. 1) the tricyclic carbazole system is essentially planar (r.m.s. deviation of all non-hydrogen atoms = 0.0100 Å), with a dihedral angle of 1.1 (3)° between two outer rings of the molecule. Other related systems are similar (Gerkin & Reppart, 1986; Duan et al., 2005). Bond distances and bond angles in the carbazole ring are comparable with those observed in similar structures (Zhou et al., 2008; Panchatcharam et al., 2011). The n-butylbromide chain adopts a semi-extended conformation, with torsion angles C10—N1—C14—C15, N1—C14—C15—C16, C14—C15—C16—C17 and C15—C16—C17—Br1 of -97.3 (4), -177.1 (3), -79.7 (4) and -178.8 (3)°, respectively. No Br···Br interactions or short intermolecular contacts are found in the crystal structure.

Related literature top

For synthesis and properties of carbazole derivatives, see: Bo et al. (1998). For chemical properties of carbazoles, see: Knolker & Reddy (2002), for their physical properties, see: Koyuncu et al. (2011), for their medicinal properties, see: Zhang et al. (2010) and for their opto-electronic and electrochemical properties, see: Taranekar et al. (2007); Morisaki et al. (2009). For related structures, see: Gerkin & Reppart (1986); Duan et al. (2005); Zhou et al. (2008); Panchatcharam et al. (2011).

Experimental top

The synthesis of 9-(4-bromobutyl)-9H-carbazole was accomplished by a modified method as reported by Bo et al., 1998. A mixture of 10.32 g (61.72 mmol) of carbazole in toluene (100 ml) containing 1,4-dibromobutane (118.2 g, 547.4 mmol) and tetrabutylammonium bromide (TBAB, 2.0 g) was stirred at 45 °C for 3 h. and then left overnight. After the aqueous layer was removed and washed three times with water and brine, the organic layer was dried over Na₂SO₄. The organic solvent was evaporated, and unreacted 1,4-dibromobutane was removed by vacuum distillation. The residue was recrystallized from ethanol to give 16.7 g (89.5% yield) of the title compound, m.p. 379 (1) K. ₁H NMR (400 MHz) δ, 8.10 (d, 2H, carbazole ring), 7.11–7.47 (m, 6H, carbazole ring), 4.35 (t, 2H, NCH₂), 3.37(t, CH₂Br), 1.91 (m, 4H, CH₂CH₂). IR (KBr): 3045 (Ar—H); 2939, 2925, 2855 (CH₂); 1620, 1593 (carbazole ring).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular conformation and atom numbering scheme for the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

9-(4-Bromobutyl)-9H-carbazole top

Crystal data top

C₁₆H₁₆BrN	D_x = 1.428 Mg m⁻³
M_r = 302.21	Melting point: 379(1) K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 18997 reflections
a = 16.0949 (4) Å	θ = 2.9–26.4°
b = 7.7012 (2) Å	µ = 2.91 mm⁻¹
c = 22.6874 (4) Å	T = 293 K
V = 2812.10 (11) Å³	Prism, colourless
Z = 8	0.24 × 0.21 × 0.17 mm
F(000) = 1232

Data collection top

Nonius KappaCCD diffractometer	2860 independent reflections
Radiation source: fine-focus sealed tube	2002 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
CCD rotation images, thick slices scans	θ_max = 26.4°, θ_min = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
T_min = 0.510, T_max = 0.589	k = −9→9
25173 measured reflections	l = −28→19

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.064P)² + 2.1492P] where P = (F_o² + 2F_c²)/3
2860 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₆H₁₆BrN	V = 2812.10 (11) Å³
M_r = 302.21	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 16.0949 (4) Å	µ = 2.91 mm⁻¹
b = 7.7012 (2) Å	T = 293 K
c = 22.6874 (4) Å	0.24 × 0.21 × 0.17 mm

Data collection top

Nonius KappaCCD diffractometer	2860 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2002 reflections with I > 2σ(I)
T_min = 0.510, T_max = 0.589	R_int = 0.042
25173 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.03	Δρ_max = 0.38 e Å⁻³
2860 reflections	Δρ_min = −0.45 e Å⁻³
163 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
Br	0.35086 (4)	1.17737 (6)	0.51126 (3)	0.1073 (3)
N1	0.43223 (16)	0.4566 (3)	0.63370 (11)	0.0617 (6)
C1	0.5664 (2)	0.4352 (6)	0.57887 (17)	0.0885 (11)
H1	0.5559	0.5272	0.5534	0.106*
C2	0.6389 (3)	0.3424 (9)	0.5758 (2)	0.1156 (19)
H2	0.6783	0.3726	0.5476	0.139*
C3	0.6552 (3)	0.2047 (9)	0.6134 (3)	0.118 (2)
H3	0.7049	0.1442	0.6098	0.141*
C4	0.5985 (3)	0.1559 (6)	0.6562 (2)	0.0960 (14)
H4	0.6096	0.0633	0.6813	0.115*
C5	0.4308 (3)	0.1312 (5)	0.74590 (18)	0.0816 (11)
H5	0.4668	0.0449	0.7589	0.098*
C6	0.3562 (3)	0.1551 (6)	0.7728 (2)	0.0954 (14)
H6	0.3414	0.0846	0.8045	0.115*
C7	0.3019 (3)	0.2824 (5)	0.75390 (18)	0.0859 (11)
H7	0.2510	0.2951	0.7728	0.103*
C8	0.3215 (2)	0.3911 (5)	0.70768 (16)	0.0702 (9)
H8	0.2848	0.4770	0.6953	0.084*
C10	0.5093 (2)	0.3865 (5)	0.62154 (14)	0.0655 (8)
C11	0.5247 (2)	0.2484 (5)	0.66088 (16)	0.0681 (9)
C12	0.4529 (2)	0.2368 (4)	0.69877 (14)	0.0624 (8)
C13	0.39748 (19)	0.3677 (4)	0.68040 (14)	0.0578 (7)
C14	0.3937 (2)	0.6011 (4)	0.60257 (15)	0.0690 (9)
H14A	0.3347	0.5782	0.5985	0.083*
H14B	0.4172	0.6086	0.5633	0.083*
C15	0.4052 (3)	0.7739 (5)	0.63337 (18)	0.0841 (11)
H15A	0.4641	0.8002	0.6356	0.101*
H15B	0.3841	0.7652	0.6733	0.101*
C16	0.3595 (2)	0.9255 (5)	0.60072 (19)	0.0807 (10)
H16A	0.3055	0.8862	0.5872	0.097*
H16B	0.3510	1.0218	0.6277	0.097*
C17	0.4087 (3)	0.9825 (5)	0.55080 (19)	0.0903 (11)
H17A	0.4160	0.8872	0.5233	0.108*
H17B	0.4631	1.0198	0.5641	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.1314 (5)	0.0737 (3)	0.1168 (4)	−0.0018 (2)	−0.0395 (3)	0.0214 (2)
N1	0.0734 (16)	0.0522 (14)	0.0593 (15)	0.0028 (12)	−0.0059 (12)	0.0041 (12)
C1	0.086 (2)	0.113 (3)	0.066 (2)	−0.008 (2)	0.002 (2)	−0.015 (2)
C2	0.083 (3)	0.180 (6)	0.084 (3)	0.001 (3)	0.003 (2)	−0.043 (4)
C3	0.081 (3)	0.167 (6)	0.106 (4)	0.039 (3)	−0.023 (3)	−0.062 (4)
C4	0.090 (3)	0.102 (3)	0.096 (3)	0.032 (2)	−0.035 (3)	−0.031 (2)
C5	0.101 (3)	0.063 (2)	0.081 (2)	−0.009 (2)	−0.031 (2)	0.0146 (18)
C6	0.115 (4)	0.088 (3)	0.083 (3)	−0.033 (3)	−0.014 (3)	0.025 (2)
C7	0.081 (3)	0.095 (3)	0.081 (2)	−0.023 (2)	0.000 (2)	0.006 (2)
C8	0.0662 (19)	0.069 (2)	0.075 (2)	−0.0044 (17)	−0.0103 (17)	0.0006 (18)
C10	0.072 (2)	0.0667 (19)	0.0577 (18)	−0.0047 (16)	−0.0081 (16)	−0.0118 (16)
C11	0.070 (2)	0.0630 (19)	0.071 (2)	0.0079 (17)	−0.0221 (17)	−0.0164 (17)
C12	0.075 (2)	0.0460 (15)	0.0662 (19)	−0.0012 (15)	−0.0232 (16)	−0.0021 (14)
C13	0.0655 (18)	0.0486 (15)	0.0595 (17)	−0.0051 (14)	−0.0124 (15)	−0.0006 (13)
C14	0.086 (2)	0.0568 (18)	0.0639 (19)	−0.0002 (17)	−0.0141 (17)	0.0060 (15)
C15	0.106 (3)	0.066 (2)	0.080 (2)	−0.0028 (19)	−0.013 (2)	−0.0008 (18)
C16	0.079 (2)	0.067 (2)	0.096 (3)	−0.0004 (17)	0.0006 (19)	−0.0061 (19)
C17	0.098 (3)	0.077 (2)	0.095 (3)	−0.003 (2)	−0.010 (2)	0.008 (2)

Geometric parameters (Å, º) top

Br—C17	1.981 (4)	C7—C8	1.378 (5)
N1—C13	1.380 (4)	C7—H7	0.9300
N1—C10	1.380 (4)	C8—C13	1.383 (5)
N1—C14	1.457 (4)	C8—H8	0.9300
C1—C2	1.371 (7)	C10—C11	1.411 (5)
C1—C10	1.387 (5)	C11—C12	1.442 (5)
C1—H1	0.9300	C12—C13	1.409 (4)
C2—C3	1.385 (9)	C14—C15	1.514 (5)
C2—H2	0.9300	C14—H14A	0.9700
C3—C4	1.386 (8)	C14—H14B	0.9700
C3—H3	0.9300	C15—C16	1.567 (5)
C4—C11	1.389 (5)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C5—C6	1.360 (6)	C16—C17	1.450 (6)
C5—C12	1.389 (5)	C16—H16A	0.9700
C5—H5	0.9300	C16—H16B	0.9700
C6—C7	1.382 (6)	C17—H17A	0.9700
C6—H6	0.9300	C17—H17B	0.9700

C13—N1—C10	108.9 (3)	C10—C11—C12	106.5 (3)
C13—N1—C14	125.4 (3)	C5—C12—C13	118.9 (4)
C10—N1—C14	125.8 (3)	C5—C12—C11	134.4 (3)
C2—C1—C10	117.3 (5)	C13—C12—C11	106.6 (3)
C2—C1—H1	121.3	N1—C13—C8	129.6 (3)
C10—C1—H1	121.3	N1—C13—C12	109.0 (3)
C1—C2—C3	121.9 (5)	C8—C13—C12	121.4 (3)
C1—C2—H2	119.0	N1—C14—C15	113.3 (3)
C3—C2—H2	119.0	N1—C14—H14A	108.9
C2—C3—C4	121.0 (4)	C15—C14—H14A	108.9
C2—C3—H3	119.5	N1—C14—H14B	108.9
C4—C3—H3	119.5	C15—C14—H14B	108.9
C3—C4—C11	118.5 (5)	H14A—C14—H14B	107.7
C3—C4—H4	120.7	C14—C15—C16	112.3 (3)
C11—C4—H4	120.7	C14—C15—H15A	109.1
C6—C5—C12	119.6 (4)	C16—C15—H15A	109.1
C6—C5—H5	120.2	C14—C15—H15B	109.1
C12—C5—H5	120.2	C16—C15—H15B	109.1
C5—C6—C7	120.9 (4)	H15A—C15—H15B	107.9
C5—C6—H6	119.5	C17—C16—C15	109.7 (3)
C7—C6—H6	119.5	C17—C16—H16A	109.7
C8—C7—C6	121.6 (4)	C15—C16—H16A	109.7
C8—C7—H7	119.2	C17—C16—H16B	109.7
C6—C7—H7	119.2	C15—C16—H16B	109.7
C7—C8—C13	117.6 (3)	H16A—C16—H16B	108.2
C7—C8—H8	121.2	C16—C17—Br	109.0 (3)
C13—C8—H8	121.2	C16—C17—H17A	109.9
N1—C10—C1	129.0 (4)	Br—C17—H17A	109.9
N1—C10—C11	109.0 (3)	C16—C17—H17B	109.9
C1—C10—C11	122.0 (4)	Br—C17—H17B	109.9
C4—C11—C10	119.3 (4)	H17A—C17—H17B	108.3
C4—C11—C12	134.3 (4)

C10—C1—C2—C3	0.2 (7)	C4—C11—C12—C5	1.6 (7)
C1—C2—C3—C4	−0.5 (8)	C10—C11—C12—C5	−179.1 (4)
C2—C3—C4—C11	−0.1 (7)	C4—C11—C12—C13	−179.0 (4)
C12—C5—C6—C7	0.2 (6)	C10—C11—C12—C13	0.3 (3)
C5—C6—C7—C8	−0.7 (7)	C10—N1—C13—C8	−179.7 (3)
C6—C7—C8—C13	0.4 (6)	C14—N1—C13—C8	0.4 (5)
C13—N1—C10—C1	−179.4 (3)	C10—N1—C13—C12	−0.2 (3)
C14—N1—C10—C1	0.5 (5)	C14—N1—C13—C12	179.9 (3)
C13—N1—C10—C11	0.4 (3)	C7—C8—C13—N1	179.9 (3)
C14—N1—C10—C11	−179.7 (3)	C7—C8—C13—C12	0.5 (5)
C2—C1—C10—N1	−179.6 (4)	C5—C12—C13—N1	179.5 (3)
C2—C1—C10—C11	0.6 (5)	C11—C12—C13—N1	0.0 (3)
C3—C4—C11—C10	0.9 (5)	C5—C12—C13—C8	−1.0 (5)
C3—C4—C11—C12	−179.9 (4)	C11—C12—C13—C8	179.5 (3)
N1—C10—C11—C4	178.9 (3)	C13—N1—C14—C15	82.5 (4)
C1—C10—C11—C4	−1.2 (5)	C10—N1—C14—C15	−97.3 (4)
N1—C10—C11—C12	−0.4 (3)	N1—C14—C15—C16	−177.1 (3)
C1—C10—C11—C12	179.4 (3)	C14—C15—C16—C17	−79.7 (4)
C6—C5—C12—C13	0.6 (5)	C15—C16—C17—Br	−178.8 (3)
C6—C5—C12—C11	180.0 (4)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆BrN
M_r	302.21
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	16.0949 (4), 7.7012 (2), 22.6874 (4)
V (Å³)	2812.10 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.91
Crystal size (mm)	0.24 × 0.21 × 0.17

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.510, 0.589
No. of measured, independent and observed [I > 2σ(I)] reflections	25173, 2860, 2002
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.146, 1.03
No. of reflections	2860
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.45

Computer programs: COLLECT (Nonius, 2000), SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK (Otwinowski & Minor, 1997, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Acknowledgements

RMF is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge licence to the Cambridge Structural Database. RMF also thanks the Universidad del Valle, Colombia, and CG thanks the Universidad San Buenaventura, Cali, Colombia, for partial financial support.

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