9-(4-Bromo­but­yl)-9H-carbazole

Wang, Q.-P.; Chang, J.-J.; Zhang, H.-Z.; Lv, J.-S.; Zhou, C.-H.

doi:10.1107/S1600536812010987

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1112

doi:10.1107/S1600536812010987

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

Qing-Peng Wang,^a Juan-Juan Chang,^a Hui-Zhen Zhang,^a Jing-Song Lv ^a and Cheng-He Zhou ^a ^*

^aLaboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: zhouch@swu.edu.cn

(Received 7 March 2012; accepted 13 March 2012; online 17 March 2012)

In the title compound, C₁₆H₁₆BrN, the bromobutyl group lies on one side of the carbazole ring plane and has a zigzag shape. The dihedral angle between the two benzene rings is 0.55°. In the crystal, molecules are connected by van der Waals interactions.

Related literature

For charge-transport properties and π-conjugated systems in carbazoles, see: Zhang et al. (2010a ). For the bioactivity of carbazole derivatives, see: Yan et al. (2011 ). For the synthesis of the title compound, see: Zhang et al. (2010b ).

Experimental

Crystal data

C₁₆H₁₆BrN
M_r = 302.20
Orthorhombic, P b c a
a = 7.696 (3) Å
b = 22.658 (8) Å
c = 16.030 (6) Å
V = 2795.3 (18) Å³
Z = 8
Mo Kα radiation
μ = 2.92 mm⁻¹
T = 296 K
0.35 × 0.33 × 0.32 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.428, T_max = 0.455
13981 measured reflections
2460 independent reflections
1252 reflections with I > 2σ(I)
R_int = 0.094

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.145
S = 0.97
2460 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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 global, I. DOI: 10.1107/S1600536812010987/rk2343sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010987/rk2343Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812010987/rk2343Isup3.cml

checkCIF report

Comment top

Carbazole and its derivatives as an important type of aromatic compounds are being actively investigated for their special structural characteristics with desirable electronic charge-transport properties and π-conjugated system (Zhang et al., 2010a). Large amount of bioactive carbazole derivatives have been reported to exert diverse biological activities such as antitumor, antimicrobial, antihistaminic, antioxidative, anti-inflammatory ones and so on (Yan et al., 2011). Our interest is to develop novel carbazole compounds as medicinal agents. Herein, the molecular structure of the title compound, I, is reported.

The X-ray analysis of I shows that the carbon C4 and carbazole moiety (N1/C5–C16) belong to the same plane. The bromobutyl moiety lies in the same side of the carbon plane.

Related literature top

For charge-transport properties and π-conjugated systems in carbazoles, see: Zhang et al. (2010a). For the bioactivity of carbazole derivatives, see: Yan et al. (2011). For the synthesis of the title compound, see: Zhang et al. (2010b).

Experimental top

The title compound was synthesized according to the procedure of Zhang et al. (2010b). Single crystals were grown by slow evaporation of a solution of I in CHCl₃ at room temperature.

Structure description top

The X-ray analysis of I shows that the carbon C4 and carbazole moiety (N1/C5–C16) belong to the same plane. The bromobutyl moiety lies in the same side of the carbon plane.

For charge-transport properties and π-conjugated systems in carbazoles, see: Zhang et al. (2010a). For the bioactivity of carbazole derivatives, see: Yan et al. (2011). For the synthesis of the title compound, see: Zhang et al. (2010b).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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. H atoms are presented as a small spheres of arbitrary radius.

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

Crystal data top

C₁₆H₁₆BrN	F(000) = 1232
M_r = 302.20	D_x = 1.436 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1683 reflections
a = 7.696 (3) Å	θ = 2.2–20.5°
b = 22.658 (8) Å	µ = 2.92 mm⁻¹
c = 16.030 (6) Å	T = 296 K
V = 2795.3 (18) Å³	Block, colourless
Z = 8	0.35 × 0.33 × 0.32 mm

Data collection top

Bruker SMART CCD diffractometer	2460 independent reflections
Radiation source: fine-focus sealed tube	1252 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.094
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.428, T_max = 0.455	k = −26→23
13981 measured reflections	l = −19→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0728P)²] where P = (F_o² + 2F_c²)/3
2460 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₆H₁₆BrN	V = 2795.3 (18) Å³
M_r = 302.20	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.696 (3) Å	µ = 2.92 mm⁻¹
b = 22.658 (8) Å	T = 296 K
c = 16.030 (6) Å	0.35 × 0.33 × 0.32 mm

Data collection top

Bruker SMART CCD diffractometer	2460 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1252 reflections with I > 2σ(I)
T_min = 0.428, T_max = 0.455	R_int = 0.094
13981 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 0.97	Δρ_max = 0.35 e Å⁻³
2460 reflections	Δρ_min = −0.42 e Å⁻³
163 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Br1	1.17750 (8)	0.51102 (3)	0.14901 (4)	0.0961 (4)
N1	0.4563 (4)	0.63416 (15)	0.0682 (2)	0.0503 (9)
C1	0.9838 (6)	0.5506 (2)	0.0916 (3)	0.0804 (16)
H1A	1.0214	0.5640	0.0371	0.097*
H1B	0.8887	0.5230	0.0840	0.097*
C2	0.9256 (7)	0.6005 (2)	0.1406 (3)	0.0728 (15)
H2A	1.0216	0.6275	0.1495	0.087*
H2B	0.8853	0.5869	0.1946	0.087*
C3	0.7738 (6)	0.6334 (2)	0.0939 (3)	0.0710 (16)
H3A	0.7660	0.6736	0.1143	0.085*
H3B	0.7995	0.6349	0.0347	0.085*
C4	0.6020 (6)	0.60279 (19)	0.1069 (3)	0.0589 (12)
H4A	0.6086	0.5633	0.0837	0.071*
H4B	0.5804	0.5991	0.1662	0.071*
C5	0.3858 (6)	0.6217 (2)	−0.0087 (3)	0.0534 (12)
C6	0.4334 (8)	0.5788 (2)	−0.0656 (3)	0.0744 (15)
H6	0.5249	0.5531	−0.0549	0.089*
C7	0.3397 (11)	0.5757 (3)	−0.1393 (4)	0.107 (2)
H7	0.3692	0.5475	−0.1791	0.128*
C8	0.2017 (10)	0.6140 (4)	−0.1546 (4)	0.106 (3)
H8	0.1403	0.6107	−0.2044	0.127*
C9	0.1550 (7)	0.6562 (3)	−0.0986 (4)	0.0820 (17)
H9	0.0626	0.6815	−0.1095	0.098*
C10	0.2482 (6)	0.6607 (2)	−0.0248 (3)	0.0546 (12)
C11	0.2370 (5)	0.6987 (2)	0.0468 (3)	0.0517 (12)
C12	0.1309 (6)	0.7458 (2)	0.0690 (4)	0.0684 (15)
H12	0.0438	0.7587	0.0331	0.082*
C13	0.1557 (7)	0.7729 (3)	0.1436 (4)	0.0810 (17)
H13	0.0852	0.8046	0.1584	0.097*
C14	0.2847 (7)	0.7542 (2)	0.1985 (4)	0.0744 (16)
H14	0.2990	0.7734	0.2493	0.089*
C15	0.3906 (6)	0.7079 (2)	0.1782 (3)	0.0576 (12)
H15	0.4762	0.6952	0.2150	0.069*
C16	0.3682 (5)	0.68078 (19)	0.1028 (3)	0.0462 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0657 (4)	0.1089 (6)	0.1138 (6)	0.0220 (3)	0.0026 (3)	0.0376 (4)
N1	0.046 (2)	0.051 (2)	0.054 (3)	0.0042 (18)	−0.0053 (18)	0.0027 (19)
C1	0.068 (4)	0.086 (4)	0.087 (4)	0.003 (3)	0.000 (3)	0.013 (3)
C2	0.062 (3)	0.089 (4)	0.068 (4)	−0.010 (3)	0.001 (3)	−0.007 (3)
C3	0.049 (3)	0.070 (3)	0.094 (5)	0.004 (2)	0.000 (3)	0.017 (3)
C4	0.046 (3)	0.059 (3)	0.072 (3)	0.006 (2)	−0.002 (3)	0.011 (3)
C5	0.055 (3)	0.047 (3)	0.058 (3)	−0.011 (2)	0.008 (3)	0.006 (3)
C6	0.101 (4)	0.060 (3)	0.062 (4)	−0.010 (3)	0.003 (3)	0.004 (3)
C7	0.171 (8)	0.082 (5)	0.067 (5)	−0.049 (5)	0.010 (5)	−0.003 (4)
C8	0.151 (7)	0.095 (5)	0.072 (5)	−0.050 (5)	−0.043 (5)	0.022 (4)
C9	0.090 (4)	0.085 (4)	0.071 (4)	−0.030 (3)	−0.028 (4)	0.031 (4)
C10	0.050 (3)	0.060 (3)	0.054 (4)	−0.014 (2)	−0.003 (2)	0.015 (3)
C11	0.036 (2)	0.056 (3)	0.063 (4)	−0.002 (2)	0.003 (2)	0.024 (3)
C12	0.053 (3)	0.074 (4)	0.079 (4)	0.011 (3)	0.007 (3)	0.028 (3)
C13	0.075 (4)	0.071 (4)	0.097 (5)	0.020 (3)	0.030 (4)	0.013 (4)
C14	0.087 (4)	0.077 (4)	0.060 (4)	0.007 (3)	0.018 (3)	0.004 (3)
C15	0.056 (3)	0.067 (3)	0.050 (3)	0.003 (3)	0.003 (2)	0.009 (3)
C16	0.043 (3)	0.049 (3)	0.046 (3)	−0.002 (2)	0.006 (2)	0.010 (2)

Geometric parameters (Å, º) top

Br1—C1	1.968 (5)	C6—H6	0.9300
N1—C16	1.372 (5)	C7—C8	1.394 (10)
N1—C5	1.377 (5)	C7—H7	0.9300
N1—C4	1.465 (5)	C8—C9	1.361 (9)
C1—C2	1.447 (7)	C8—H8	0.9300
C1—H1A	0.9700	C9—C10	1.386 (7)
C1—H1B	0.9700	C9—H9	0.9300
C2—C3	1.575 (6)	C10—C11	1.437 (7)
C2—H2A	0.9700	C11—C12	1.391 (7)
C2—H2B	0.9700	C11—C16	1.411 (6)
C3—C4	1.507 (6)	C12—C13	1.358 (7)
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700	C13—C14	1.392 (8)
C4—H4A	0.9700	C13—H13	0.9300
C4—H4B	0.9700	C14—C15	1.367 (6)
C5—C6	1.382 (6)	C14—H14	0.9300
C5—C10	1.403 (6)	C15—C16	1.368 (6)
C6—C7	1.386 (8)	C15—H15	0.9300

C16—N1—C5	108.9 (4)	C7—C6—H6	121.3
C16—N1—C4	125.6 (4)	C6—C7—C8	121.0 (7)
C5—N1—C4	125.5 (4)	C6—C7—H7	119.5
C2—C1—Br1	109.7 (4)	C8—C7—H7	119.5
C2—C1—H1A	109.7	C9—C8—C7	121.5 (6)
Br1—C1—H1A	109.7	C9—C8—H8	119.2
C2—C1—H1B	109.7	C7—C8—H8	119.2
Br1—C1—H1B	109.7	C8—C9—C10	118.5 (6)
H1A—C1—H1B	108.2	C8—C9—H9	120.7
C1—C2—C3	110.0 (4)	C10—C9—H9	120.7
C1—C2—H2A	109.7	C9—C10—C5	120.1 (5)
C3—C2—H2A	109.7	C9—C10—C11	133.9 (5)
C1—C2—H2B	109.7	C5—C10—C11	106.0 (4)
C3—C2—H2B	109.7	C12—C11—C16	118.5 (5)
H2A—C2—H2B	108.2	C12—C11—C10	134.4 (5)
C4—C3—C2	111.6 (4)	C16—C11—C10	107.1 (4)
C4—C3—H3A	109.3	C13—C12—C11	119.4 (5)
C2—C3—H3A	109.3	C13—C12—H12	120.3
C4—C3—H3B	109.3	C11—C12—H12	120.3
C2—C3—H3B	109.3	C12—C13—C14	121.3 (5)
H3A—C3—H3B	108.0	C12—C13—H13	119.4
N1—C4—C3	113.0 (4)	C14—C13—H13	119.4
N1—C4—H4A	109.0	C15—C14—C13	120.6 (5)
C3—C4—H4A	109.0	C15—C14—H14	119.7
N1—C4—H4B	109.0	C13—C14—H14	119.7
C3—C4—H4B	109.0	C14—C15—C16	118.6 (4)
H4A—C4—H4B	107.8	C14—C15—H15	120.7
N1—C5—C6	129.1 (5)	C16—C15—H15	120.7
N1—C5—C10	109.5 (4)	C15—C16—N1	129.8 (4)
C6—C5—C10	121.4 (5)	C15—C16—C11	121.6 (4)
C5—C6—C7	117.4 (6)	N1—C16—C11	108.5 (4)
C5—C6—H6	121.3

Br1—C1—C2—C3	178.5 (3)	C9—C10—C11—C12	−1.1 (9)
C1—C2—C3—C4	80.9 (5)	C5—C10—C11—C12	179.6 (5)
C16—N1—C4—C3	−83.0 (5)	C9—C10—C11—C16	179.2 (5)
C5—N1—C4—C3	96.9 (5)	C5—C10—C11—C16	−0.1 (5)
C2—C3—C4—N1	176.7 (4)	C16—C11—C12—C13	−0.3 (7)
C16—N1—C5—C6	179.6 (4)	C10—C11—C12—C13	180.0 (5)
C4—N1—C5—C6	−0.3 (7)	C11—C12—C13—C14	−0.3 (8)
C16—N1—C5—C10	−0.2 (5)	C12—C13—C14—C15	0.2 (8)
C4—N1—C5—C10	179.8 (4)	C13—C14—C15—C16	0.6 (7)
N1—C5—C6—C7	−180.0 (5)	C14—C15—C16—N1	179.9 (4)
C10—C5—C6—C7	−0.2 (7)	C14—C15—C16—C11	−1.2 (6)
C5—C6—C7—C8	−0.6 (8)	C5—N1—C16—C15	179.2 (4)
C6—C7—C8—C9	0.6 (10)	C4—N1—C16—C15	−0.9 (7)
C7—C8—C9—C10	0.1 (9)	C5—N1—C16—C11	0.2 (4)
C8—C9—C10—C5	−0.9 (7)	C4—N1—C16—C11	−179.9 (3)
C8—C9—C10—C11	179.9 (5)	C12—C11—C16—C15	1.1 (6)
N1—C5—C10—C9	−179.2 (4)	C10—C11—C16—C15	−179.1 (4)
C6—C5—C10—C9	0.9 (7)	C12—C11—C16—N1	−179.8 (3)
N1—C5—C10—C11	0.2 (5)	C10—C11—C16—N1	0.0 (5)
C6—C5—C10—C11	−179.6 (4)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆BrN
M_r	302.20
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	7.696 (3), 22.658 (8), 16.030 (6)
V (Å³)	2795.3 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.92
Crystal size (mm)	0.35 × 0.33 × 0.32

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.428, 0.455
No. of measured, independent and observed [I > 2σ(I)] reflections	13981, 2460, 1252
R_int	0.094
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.145, 0.97
No. of reflections	2460
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.42

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was partially supported by the National Natural Science Foundation of China (No. 21172181), the Key Program of the Natural Science Foundation of Chongqing (CSTC2012jjB10020), the Specialized Research Fund for the Doctoral Program of Higher Education of China (SRFDP 20110182110007) and the Research Funds for the Central Universities (XDJK2012B026).

References

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