9-Hexyl-3-iodo-9H-carbazole

Geng, W.-Q.; Xu, G.-Y.; Zhou, H.-P.

doi:10.1107/S1600536809054415

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o230

doi:10.1107/S1600536809054415

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9-Hexyl-3-iodo-9H-carbazole

Wen-Qian Geng,^a Guo-Yi Xu ^a and Hong-Ping Zhou ^a ^*

^aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and Key Laboratory of Functional Inorganic Materials Chemistry, Hefei 230039, People's Republic of China
^*Correspondence e-mail: zhpzhp@263.net

(Received 12 December 2009; accepted 17 December 2009; online 24 December 2009)

In the title molecule, C₁₈H₂₀IN, the tricyclic carbazole system is essentially planar with the two outer rings forming a dihedral angle of 0.43 (8)°. The crystal packing exhibits no short intermolecular contacts.

Related literature

For the crystal structures of related carbazole derivatives, see: Zhou et al. (2007 , 2008 ); Chen et al. (2009 ).

Experimental

Crystal data

C₁₈H₂₀IN
M_r = 377.25
Monoclinic, P 2₁ /c
a = 10.7105 (2) Å
b = 4.6816 (10) Å
c = 33.9661 (18) Å
β = 105.106 (8)°
V = 1644.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.94 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.594, T_max = 0.698
13335 measured reflections
2904 independent reflections
2123 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.164
S = 1.14
2904 reflections
182 parameters
13 restraints
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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/S1600536809054415/cv2679sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809054415/cv2679Isup2.hkl

checkCIF report

Comment top

In continuation of our study of carbazole derivatives (Zhou et al., 2007, 2008) we present here the title compound, (I). In (I) (Fig. 1), the bond lengths and angles show normal values comparable with those observed in the related compounds (Zhou et al., 2008; Chen et al., 2009). Two outer rings form a dihedral angle of 0.43 (8) °. The crystal packing exhibits no essentially short intermolecular contacts.

Related literature top

For the crystal structures of related carbazole derivatives, see: Zhou et al. (2007, 2008); Chen et al. (2009).

Experimental top

A 50 ml round bottom flask was charged with 9-hexlylcarbazole (2.51 g, 10 mmol) and 10 ml e thanol. ICl (2.50 g, 15 mmol, dissolved in 4 ml ethanol) was added to the stirring solution at 343 k after 9-(hex-1-yl)-3-iodocarbazole was completely dissolved. At the end of the reaction was judged by TLC analysis after 2 h. The solution was filtered through filter paper and precipitates were obtained as a light blue solid in 89% (4.48 g) yield.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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. Molecular structure of (I) with displacement ellipsoids shown at 30% probability level.

9-Hexyl-3-iodo-9H-carbazole top

Crystal data top

C₁₈H₂₀IN	F(000) = 752
M_r = 377.25	D_x = 1.524 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 4151 reflections
a = 10.7105 (2) Å	θ = 2.6–23.7°
b = 4.6816 (10) Å	µ = 1.94 mm⁻¹
c = 33.9661 (18) Å	T = 298 K
β = 105.106 (8)°	Bar, colourless
V = 1644.3 (4) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2904 independent reflections
Radiation source: fine-focus sealed tube	2123 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.594, T_max = 0.698	k = −5→5
13335 measured reflections	l = −40→40

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2904 reflections	(Δ/σ)_max = 0.002
182 parameters	Δρ_max = 1.03 e Å⁻³
13 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₁₈H₂₀IN	V = 1644.3 (4) Å³
M_r = 377.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.7105 (2) Å	µ = 1.94 mm⁻¹
b = 4.6816 (10) Å	T = 298 K
c = 33.9661 (18) Å	0.30 × 0.20 × 0.20 mm
β = 105.106 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2904 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2123 reflections with I > 2σ(I)
T_min = 0.594, T_max = 0.698	R_int = 0.024
13335 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	13 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.14	Δρ_max = 1.03 e Å⁻³
2904 reflections	Δρ_min = −0.61 e Å⁻³
182 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
I1	−0.28721 (3)	0.22226 (10)	0.854577 (12)	0.1016 (3)
N1	0.2490 (4)	0.7102 (7)	0.85154 (11)	0.0642 (10)
C1	0.0702 (5)	0.6986 (10)	0.88720 (15)	0.0764 (14)
H1	0.1078	0.8288	0.9075	0.092*
C2	−0.0462 (4)	0.5812 (12)	0.88584 (12)	0.0784 (13)
H2	−0.0887	0.6318	0.9054	0.094*
C3	−0.1033 (4)	0.3863 (11)	0.85567 (12)	0.0691 (11)
C4	−0.0449 (4)	0.3024 (9)	0.82657 (13)	0.0642 (11)
H4	−0.0839	0.1699	0.8068	0.077*
C5	0.1625 (4)	0.2277 (9)	0.76745 (13)	0.0642 (12)
H5	0.0931	0.1082	0.7561	0.077*
C6	0.2669 (5)	0.2482 (9)	0.75017 (15)	0.0733 (14)
H6	0.2675	0.1406	0.7272	0.088*
C7	0.3691 (4)	0.4269 (11)	0.76693 (14)	0.0752 (12)
H7	0.4373	0.4394	0.7548	0.090*
C8	0.3731 (4)	0.5878 (10)	0.80120 (12)	0.0677 (11)
H8	0.4433	0.7053	0.8125	0.081*
C9	0.1323 (4)	0.6213 (9)	0.85775 (11)	0.0588 (10)
C10	0.0761 (3)	0.4209 (9)	0.82713 (10)	0.0550 (9)
C11	0.1639 (3)	0.3892 (9)	0.80204 (10)	0.0543 (9)
C12	0.2694 (3)	0.5687 (8)	0.81814 (10)	0.0544 (9)
C13	0.3408 (4)	0.9010 (10)	0.87894 (12)	0.0705 (11)
H13A	0.2938	1.0335	0.8917	0.085*
H13B	0.3879	1.0110	0.8633	0.085*
C14	0.4357 (5)	0.7305 (8)	0.91164 (16)	0.0714 (13)
H14A	0.3878	0.6282	0.9278	0.086*
H14B	0.4777	0.5899	0.8985	0.086*
C15	0.5381 (4)	0.9110 (11)	0.93974 (13)	0.0745 (12)
H15A	0.5777	1.0328	0.9233	0.089*
H15B	0.4967	1.0340	0.9555	0.089*
C16	0.6420 (6)	0.7450 (10)	0.96843 (19)	0.096 (2)
H16A	0.6773	0.6077	0.9528	0.115*
H16B	0.6037	0.6386	0.9868	0.115*
C17	0.7505 (5)	0.9222 (13)	0.99323 (18)	0.118 (2)
H17A	0.7797	1.0512	0.9751	0.142*
H17B	0.7178	1.0378	1.0121	0.142*
C18	0.8625 (7)	0.7562 (13)	1.0167 (3)	0.144 (3)
H18A	0.9236	0.8826	1.0340	0.216*
H18B	0.9030	0.6609	0.9983	0.216*
H18C	0.8338	0.6170	1.0332	0.216*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0687 (3)	0.1321 (5)	0.1158 (4)	−0.00227 (17)	0.0452 (3)	0.0162 (2)
N1	0.054 (2)	0.068 (2)	0.065 (2)	−0.0032 (16)	0.0064 (16)	−0.0033 (15)
C1	0.075 (3)	0.086 (3)	0.066 (3)	0.011 (2)	0.015 (2)	−0.003 (2)
C2	0.073 (3)	0.104 (4)	0.063 (2)	0.018 (3)	0.027 (2)	0.009 (3)
C3	0.055 (2)	0.088 (3)	0.068 (2)	0.012 (2)	0.0223 (19)	0.017 (2)
C4	0.055 (2)	0.074 (3)	0.061 (2)	0.002 (2)	0.0105 (18)	0.0064 (19)
C5	0.052 (2)	0.073 (3)	0.064 (2)	−0.0023 (18)	0.0103 (19)	−0.0076 (18)
C6	0.066 (3)	0.086 (4)	0.069 (3)	0.001 (2)	0.021 (2)	−0.009 (2)
C7	0.058 (2)	0.087 (3)	0.086 (3)	0.003 (2)	0.029 (2)	0.008 (3)
C8	0.054 (2)	0.069 (3)	0.079 (3)	−0.006 (2)	0.0164 (19)	0.002 (2)
C9	0.055 (2)	0.064 (2)	0.054 (2)	0.009 (2)	0.0071 (17)	0.0056 (19)
C10	0.046 (2)	0.062 (2)	0.0530 (19)	0.0080 (19)	0.0067 (15)	0.0101 (18)
C11	0.0456 (19)	0.060 (2)	0.055 (2)	0.0056 (18)	0.0092 (15)	0.0071 (17)
C12	0.0479 (19)	0.057 (2)	0.0555 (19)	0.0039 (18)	0.0089 (15)	0.0050 (17)
C13	0.071 (3)	0.062 (3)	0.071 (2)	−0.005 (2)	0.006 (2)	−0.006 (2)
C14	0.071 (3)	0.062 (3)	0.077 (3)	−0.004 (2)	0.010 (2)	−0.0026 (19)
C15	0.068 (3)	0.079 (3)	0.075 (3)	−0.015 (2)	0.014 (2)	−0.009 (2)
C16	0.099 (5)	0.080 (4)	0.089 (4)	0.006 (3)	−0.009 (3)	−0.008 (2)
C17	0.118 (4)	0.090 (4)	0.121 (4)	0.005 (4)	−0.014 (3)	−0.021 (3)
C18	0.116 (6)	0.135 (6)	0.155 (6)	0.007 (4)	−0.011 (5)	−0.028 (4)

Geometric parameters (Å, º) top

I1—C3	2.106 (4)	C9—C10	1.413 (6)
N1—C12	1.379 (5)	C10—C11	1.431 (5)
N1—C9	1.385 (6)	C11—C12	1.400 (5)
N1—C13	1.467 (5)	C13—C14	1.522 (6)
C1—C2	1.351 (7)	C13—H13A	0.9700
C1—C9	1.386 (7)	C13—H13B	0.9700
C1—H1	0.9300	C14—C15	1.511 (6)
C2—C3	1.389 (7)	C14—H14A	0.9700
C2—H2	0.9300	C14—H14B	0.9700
C3—C4	1.358 (6)	C15—C16	1.492 (7)
C4—C10	1.405 (6)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C5—C11	1.394 (6)	C16—C17	1.496 (8)
C5—C6	1.395 (7)	C16—H16A	0.9700
C5—H5	0.9300	C16—H16B	0.9700
C6—C7	1.378 (7)	C17—C18	1.477 (7)
C6—H6	0.9300	C17—H17A	0.9700
C7—C8	1.378 (6)	C17—H17B	0.9700
C7—H7	0.9300	C18—H18A	0.9600
C8—C12	1.381 (5)	C18—H18B	0.9600
C8—H8	0.9300	C18—H18C	0.9600

C12—N1—C9	108.9 (3)	C8—C12—C11	122.1 (4)
C12—N1—C13	126.2 (4)	N1—C13—C14	110.7 (4)
C9—N1—C13	124.6 (4)	N1—C13—H13A	109.5
C2—C1—C9	118.8 (5)	C14—C13—H13A	109.5
C2—C1—H1	120.6	N1—C13—H13B	109.5
C9—C1—H1	120.6	C14—C13—H13B	109.5
C1—C2—C3	121.1 (4)	H13A—C13—H13B	108.1
C1—C2—H2	119.4	C15—C14—C13	113.9 (4)
C3—C2—H2	119.4	C15—C14—H14A	108.8
C4—C3—C2	121.9 (4)	C13—C14—H14A	108.8
C4—C3—I1	119.2 (4)	C15—C14—H14B	108.8
C2—C3—I1	118.9 (3)	C13—C14—H14B	108.8
C3—C4—C10	118.3 (4)	H14A—C14—H14B	107.7
C3—C4—H4	120.9	C16—C15—C14	114.6 (4)
C10—C4—H4	120.9	C16—C15—H15A	108.6
C11—C5—C6	118.9 (4)	C14—C15—H15A	108.6
C11—C5—H5	120.6	C16—C15—H15B	108.6
C6—C5—H5	120.6	C14—C15—H15B	108.6
C7—C6—C5	120.4 (4)	H15A—C15—H15B	107.6
C7—C6—H6	119.8	C15—C16—C17	114.6 (4)
C5—C6—H6	119.8	C15—C16—H16A	108.6
C6—C7—C8	121.8 (4)	C17—C16—H16A	108.6
C6—C7—H7	119.1	C15—C16—H16B	108.6
C8—C7—H7	119.1	C17—C16—H16B	108.6
C7—C8—C12	117.7 (4)	H16A—C16—H16B	107.6
C7—C8—H8	121.1	C18—C17—C16	114.5 (5)
C12—C8—H8	121.1	C18—C17—H17A	108.6
N1—C9—C1	130.8 (4)	C16—C17—H17A	108.6
N1—C9—C10	108.4 (4)	C18—C17—H17B	108.6
C1—C9—C10	120.8 (4)	C16—C17—H17B	108.6
C4—C10—C9	119.1 (4)	H17A—C17—H17B	107.6
C4—C10—C11	134.2 (4)	C17—C18—H18A	109.5
C9—C10—C11	106.7 (3)	C17—C18—H18B	109.5
C5—C11—C12	119.0 (4)	H18A—C18—H18B	109.5
C5—C11—C10	133.9 (4)	C17—C18—H18C	109.5
C12—C11—C10	107.1 (3)	H18A—C18—H18C	109.5
N1—C12—C8	128.9 (4)	H18B—C18—H18C	109.5
N1—C12—C11	109.0 (3)

C9—C1—C2—C3	0.1 (7)	C6—C5—C11—C10	180.0 (4)
C1—C2—C3—C4	0.7 (7)	C4—C10—C11—C5	−0.1 (7)
C1—C2—C3—I1	−178.2 (3)	C9—C10—C11—C5	−179.3 (4)
C2—C3—C4—C10	−0.8 (6)	C4—C10—C11—C12	179.4 (4)
I1—C3—C4—C10	178.1 (3)	C9—C10—C11—C12	0.2 (4)
C11—C5—C6—C7	−0.5 (7)	C9—N1—C12—C8	−179.2 (4)
C5—C6—C7—C8	0.8 (7)	C13—N1—C12—C8	−5.2 (6)
C6—C7—C8—C12	−1.1 (7)	C9—N1—C12—C11	0.9 (4)
C12—N1—C9—C1	179.5 (4)	C13—N1—C12—C11	175.0 (4)
C13—N1—C9—C1	5.4 (7)	C7—C8—C12—N1	−178.6 (4)
C12—N1—C9—C10	−0.8 (4)	C7—C8—C12—C11	1.2 (6)
C13—N1—C9—C10	−175.0 (3)	C5—C11—C12—N1	178.9 (3)
C2—C1—C9—N1	178.8 (4)	C10—C11—C12—N1	−0.7 (4)
C2—C1—C9—C10	−0.8 (6)	C5—C11—C12—C8	−1.0 (6)
C3—C4—C10—C9	0.1 (5)	C10—C11—C12—C8	179.5 (4)
C3—C4—C10—C11	−179.1 (4)	C12—N1—C13—C14	−84.0 (5)
N1—C9—C10—C4	−179.0 (3)	C9—N1—C13—C14	89.2 (5)
C1—C9—C10—C4	0.7 (6)	N1—C13—C14—C15	176.8 (4)
N1—C9—C10—C11	0.4 (4)	C13—C14—C15—C16	−172.3 (5)
C1—C9—C10—C11	−179.9 (4)	C14—C15—C16—C17	174.0 (6)
C6—C5—C11—C12	0.6 (6)	C15—C16—C17—C18	−170.8 (7)

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀IN
M_r	377.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.7105 (2), 4.6816 (10), 33.9661 (18)
β (°)	105.106 (8)
V (Å³)	1644.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.94
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.594, 0.698
No. of measured, independent and observed [I > 2σ(I)] reflections	13335, 2904, 2123
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.164, 1.14
No. of reflections	2904
No. of parameters	182
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.03, −0.61

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant Nos. 50703001, 20771001), the Education Committee of Anhui Province (grant No. KJ2009A52), the Young Teacher Foundation of Institutions of Higher Education of An Hui Province (grant No. 2007jq1019), the Ministry of Education and the Person with Ability Foundation of Anhui University.

References

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