N,N-Dimethyl-4-[(E)-2-(3,6,7-tribromo-9-butyl-9H-carbazol-2-yl)ethen­yl]aniline

Kumar, S.; Thomas, K.R.J.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812011336

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1121

doi:10.1107/S1600536812011336

Open

access

N,N-Dimethyl-4-[(E)-2-(3,6,7-tribromo-9-butyl-9H-carbazol-2-yl)ethenyl]aniline

Sushil Kumar,^a K. R. Justin Thomas,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aOrganic Materials Laboratory, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247 667, India, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 28 February 2012; accepted 15 March 2012; online 21 March 2012)

In the title molecule, C₂₆H₂₅Br₃N₂, a dihedral angle of 6.15 (10)° is present between the carbazole and benzene ring systems with an E conformation about the C=C bond [1.335 (4) Å]. The butyl group is almost perpendicular to the carbazole plane [C—N—C—C torsion angle = −98.7 (3)°]. In the crystal, supramolecular double chains along [-7,18,-16] are formed via C—H⋯Br and π–π interactions [centroid(carbazole five-membered ring)⋯centroid(carbazole six-membered ring) distance = 3.6333 (13) Å].

Related literature

For the use of carbazole derivatives in organic light-emitting diodes and photovoltaic devices, see: Thomas et al. (2001 , 2004 ); Wu et al. (2005 ); Lee et al. (2012 ); Ooyama et al. (2011 ). For related structures, see: Pawluć et al. (2011 ); Zhang & Zhang (2011 ); Ramathilagam et al. (2011 ).

Experimental

Crystal data

C₂₆H₂₅Br₃N₂
M_r = 605.21
Triclinic, $[P \overline 1]$
a = 9.7304 (3) Å
b = 11.3834 (4) Å
c = 11.8197 (4) Å
α = 114.308 (3)°
β = 101.957 (3)°
γ = 90.127 (3)°
V = 1161.62 (7) Å³
Z = 2
Cu Kα radiation
μ = 6.56 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.244, T_max = 0.735
10766 measured reflections
4827 independent reflections
4680 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.092
S = 1.07
4827 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 1.18 e Å⁻³
Δρ_min = −0.81 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26C⋯Br1ⁱ	0.98	2.91	3.844 (3)	161
Symmetry code: (i) x+1, y-1, z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812011336/gg2078sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812011336/gg2078Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812011336/gg2078Isup3.cml

checkCIF report

Comment top

Polysubstituted carbazole derivatives have been widely explored as functional materials for applications in organic light-emitting diodes (Thomas et al., 2001; Thomas et al., 2004; Wu et al., 2005) and photovoltaic devices (Lee et al., 2012; Ooyama et al., 2011) due to their charge transporting and amorphous properties. Though the 3,6,9-trisubstituted (Thomas et al., 2001; Thomas et al., 2004) and 2,7,9-trisubstituted carbazole (Wu et al., 2005; Lee et al., 2012) compounds have been well documented in the literature, 2,3,6,7,9-pentasubstituted carbazole derivatives are relatively rare. Herein, the synthesis and crystal structure determination of the title compound, (I), are described. Several related structures are known (Pawluć et al., 2011; Zhang & Zhang, 2011; Ramathilagam et al., 2011).

In (I), the carbazole fused-ring system is planar with the r.m.s. deviation of the 13 fitted non-hydrogen atoms = 0.006 Å; the Br1, Br2 and Br3 atoms lie 0.058 (1), 0.062 (1) and 0.043 (1) Å out of this plane, respectively. The least-squares plane through the carbazole residue forms a dihedral angle of 6.15 (10)° with the benzene ring, indicating a small twist between the terminal ring systems. This twist is manifested in the value of the C15—C14—C17—C18 torsion angle of -11.2 (4)°. The butyl group is almost perpendicular to the carbazole plane with the C1—N1—C7—C8 torsion angle being -98.7 (3)°. Finally, the conformation about the C17═C18 bond [1.335 (4) Å] is E.

In the crystal packing, molecules are linked into linear supramolecular chains via C—H···Br interactions, Fig. 2 and Table 1. These are connected into double chains along [7 18 16] via π–π interactions occurring between five- and six-membered rings of the carbazole residue [centroid(N1,C1,C6,C11,C16)···centroid(C1–C6)ⁱ = 3.6333 (13) Å, angle between rings = 0.50 (12)° for symmetry operation i: 1 - x, 1 - y, -z]. Chains assemble into layers, with no specific interactions between them. In turn, the layers stack along (2 0 2), again without specific interactions between them, Fig. 2.

Related literature top

For the use of carbazole derivatives in organic light-emitting diodes and photovoltaic devices, see: Thomas et al. (2001, 2004); Wu et al. (2005); Lee et al. (2012); Ooyama et al. (2011). For related structures, see: Pawluć et al. (2011); Zhang & Zhang (2011); Ramathilagam et al. (2011).

Experimental top

A mixture of 2,3,6,7-tetrabromo-9-butyl-9H-carbazole (0.25 g, 0.47 mmol), styrene (0.29 g, 1.96 mmol), tetrabutylammonium bromide (0.32 g, 0.98 mmol), sodium acetate (1.6 g, 19.6 mmol), Pd(OAc)₂ (4 mg) and dimethylformamide (5 ml) was heated at 383 K for 48 h. Subsequently, it was cooled, then poured into water and extracted using ethyl acetate. On removal of solvent, a residue was obtained which on purification by column chromatography on silica gel gave an orange crystalline solid. Yield: 0.12 g, 42%. M.pt: 414 K. Crystals were grown from a solution of the title compound dissolved in dichloromethane/hexanes mixture (1:9 v/v).

¹H NMR (500 MHz, CDCl₃) δ: 8.20 (s, 1 H), 8.17 (s, 1 H), 7.63 (s, 1H), 7.58 (s, 1 H), 7.51 (d, J = 9.0 Hz, 2 H), 7.43 (d, J = 16 Hz, 1 H), 7.05 (d, J = 16 Hz, 1 H), 6.74 (d, J = 9 Hz, 2 H), 4.24 (t, J = 7.5 Hz, 2 H), 3.02 (s, 6 H), 1.86–1.83 (m, 2 H), 1.42–1.37 (m, 2 H), 0.97 (t, J = 7.5 Hz, 3 H); ¹³C NMR (125 MHz, CDCl₃) δ: 150.4, 140.7, 140.5, 136.2, 131.4, 128.1, 127.8, 127.4, 125.4, 124.6, 124.4, 124.0, 122.7, 121.6, 121.4, 115.0, 114.0, 113.5, 112.5, 112.4, 105.8, 100.0, 43.2, 40.5, 30.9, 20.6, 13.9.

Structure description top

For the use of carbazole derivatives in organic light-emitting diodes and photovoltaic devices, see: Thomas et al. (2001, 2004); Wu et al. (2005); Lee et al. (2012); Ooyama et al. (2011). For related structures, see: Pawluć et al. (2011); Zhang & Zhang (2011); Ramathilagam et al. (2011).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the linear supramolecular chain in (I). The C—H···Br and π–π interactions are shown as orange and purple dashed lines, respectively.
	Fig. 3. A view in projection down the b axis of the stacking of layers, formed by non-interacting supramolecular chains, in (I). The C—H···Br and π–π interactions are shown as orange and purple dashed lines, respectively.

N,N-Dimethyl-4-[(E)-2-(3,6,7-tribromo-9-butyl-9H- carbazol-2-yl)ethenyl]aniline top

Crystal data top

C₂₆H₂₅Br₃N₂	Z = 2
M_r = 605.21	F(000) = 600
Triclinic, P1	D_x = 1.730 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.7304 (3) Å	Cell parameters from 7879 reflections
b = 11.3834 (4) Å	θ = 4.2–76.4°
c = 11.8197 (4) Å	µ = 6.56 mm⁻¹
α = 114.308 (3)°	T = 100 K
β = 101.957 (3)°	Plate, orange
γ = 90.127 (3)°	0.30 × 0.30 × 0.05 mm
V = 1161.62 (7) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4827 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4680 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.6°, θ_min = 4.2°
ω scan	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→14
T_min = 0.244, T_max = 0.735	l = −14→10
10766 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0613P)² + 0.89P] where P = (F_o² + 2F_c²)/3
4827 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 1.18 e Å⁻³
0 restraints	Δρ_min = −0.81 e Å⁻³

Crystal data top

C₂₆H₂₅Br₃N₂	γ = 90.127 (3)°
M_r = 605.21	V = 1161.62 (7) Å³
Triclinic, P1	Z = 2
a = 9.7304 (3) Å	Cu Kα radiation
b = 11.3834 (4) Å	µ = 6.56 mm⁻¹
c = 11.8197 (4) Å	T = 100 K
α = 114.308 (3)°	0.30 × 0.30 × 0.05 mm
β = 101.957 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4827 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4680 reflections with I > 2σ(I)
T_min = 0.244, T_max = 0.735	R_int = 0.021
10766 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.07	Δρ_max = 1.18 e Å⁻³
4827 reflections	Δρ_min = −0.81 e Å⁻³
282 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
Br1	0.29708 (3)	0.83996 (3)	0.02986 (2)	0.02733 (9)
Br2	0.56802 (3)	0.78783 (3)	−0.11524 (2)	0.02739 (9)
Br3	1.11706 (3)	0.35337 (3)	0.20455 (3)	0.02790 (9)
N1	0.5643 (2)	0.5740 (2)	0.27349 (19)	0.0222 (4)
N2	1.1308 (3)	0.0298 (3)	0.7703 (2)	0.0333 (5)
C1	0.5457 (2)	0.6291 (2)	0.1869 (2)	0.0209 (4)
C2	0.4366 (3)	0.6979 (2)	0.1578 (2)	0.0228 (5)
H2	0.3598	0.7132	0.1986	0.027*
C3	0.4443 (3)	0.7433 (2)	0.0664 (2)	0.0226 (5)
C4	0.5569 (3)	0.7208 (2)	0.0055 (2)	0.0227 (5)
C5	0.6653 (3)	0.6523 (2)	0.0351 (2)	0.0232 (5)
H5	0.7418	0.6373	−0.0061	0.028*
C6	0.6601 (2)	0.6056 (2)	0.1262 (2)	0.0205 (4)
C7	0.4735 (2)	0.5794 (2)	0.3587 (2)	0.0236 (5)
H7A	0.4651	0.4940	0.3615	0.028*
H7B	0.3780	0.5967	0.3240	0.028*
C8	0.5283 (3)	0.6836 (2)	0.4944 (2)	0.0263 (5)
H8A	0.4684	0.6752	0.5494	0.032*
H8B	0.6253	0.6681	0.5274	0.032*
C9	0.5301 (3)	0.8209 (3)	0.5043 (2)	0.0295 (5)
H9A	0.4321	0.8398	0.4793	0.035*
H9B	0.5833	0.8280	0.4441	0.035*
C10	0.5972 (3)	0.9205 (3)	0.6384 (3)	0.0357 (6)
H10A	0.5967	1.0074	0.6403	0.054*
H10B	0.6947	0.9029	0.6632	0.054*
H10C	0.5434	0.9155	0.6980	0.054*
C11	0.7525 (3)	0.5336 (2)	0.1799 (2)	0.0213 (4)
C12	0.8799 (3)	0.4835 (2)	0.1613 (2)	0.0223 (5)
H12	0.9246	0.4940	0.1014	0.027*
C13	0.9406 (2)	0.4177 (2)	0.2322 (2)	0.0217 (4)
C14	0.8789 (2)	0.3989 (2)	0.3234 (2)	0.0207 (4)
C15	0.7510 (3)	0.4504 (2)	0.3406 (2)	0.0216 (4)
H15	0.7059	0.4402	0.4004	0.026*
C16	0.6895 (2)	0.5168 (2)	0.2704 (2)	0.0207 (4)
C17	0.9466 (2)	0.3259 (2)	0.3949 (2)	0.0211 (4)
H17	1.0239	0.2799	0.3683	0.025*
C18	0.9070 (3)	0.3201 (2)	0.4942 (2)	0.0238 (5)
H18	0.8316	0.3687	0.5218	0.029*
C19	0.9685 (3)	0.2460 (2)	0.5642 (2)	0.0222 (5)
C20	0.9072 (3)	0.2399 (3)	0.6593 (2)	0.0258 (5)
H20	0.8267	0.2851	0.6769	0.031*
C21	0.9600 (3)	0.1702 (3)	0.7288 (3)	0.0274 (5)
H21	0.9152	0.1683	0.7923	0.033*
C22	1.0787 (3)	0.1029 (2)	0.7058 (2)	0.0245 (5)
C23	1.1426 (3)	0.1108 (2)	0.6119 (2)	0.0253 (5)
H23	1.2248	0.0679	0.5958	0.030*
C24	1.0881 (3)	0.1797 (2)	0.5433 (2)	0.0243 (5)
H24	1.1331	0.1822	0.4801	0.029*
C25	1.2647 (3)	−0.0235 (3)	0.7574 (3)	0.0300 (5)
H25A	1.3375	0.0461	0.7772	0.045*
H25B	1.2562	−0.0885	0.6698	0.045*
H25C	1.2909	−0.0641	0.8166	0.045*
C26	1.0606 (3)	0.0186 (3)	0.8627 (3)	0.0328 (6)
H26A	0.9602	−0.0093	0.8233	0.049*
H26B	1.0708	0.1029	0.9360	0.049*
H26C	1.1033	−0.0453	0.8912	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02941 (16)	0.02848 (15)	0.02854 (15)	0.00817 (11)	0.00398 (11)	0.01757 (11)
Br2	0.03297 (16)	0.03048 (15)	0.02791 (15)	0.00781 (11)	0.00784 (11)	0.02082 (12)
Br3	0.02538 (15)	0.03522 (16)	0.03272 (16)	0.01107 (11)	0.01128 (11)	0.02151 (12)
N1	0.0211 (9)	0.0276 (10)	0.0239 (9)	0.0051 (8)	0.0045 (8)	0.0172 (8)
N2	0.0314 (12)	0.0441 (13)	0.0403 (13)	0.0144 (10)	0.0105 (10)	0.0322 (11)
C1	0.0224 (11)	0.0212 (10)	0.0206 (10)	0.0004 (9)	0.0019 (8)	0.0117 (9)
C2	0.0244 (11)	0.0240 (11)	0.0226 (11)	0.0030 (9)	0.0040 (9)	0.0130 (9)
C3	0.0235 (11)	0.0209 (10)	0.0229 (11)	0.0036 (9)	0.0010 (9)	0.0109 (9)
C4	0.0295 (12)	0.0206 (10)	0.0194 (10)	0.0024 (9)	0.0017 (9)	0.0117 (9)
C5	0.0274 (12)	0.0224 (11)	0.0224 (11)	0.0022 (9)	0.0060 (9)	0.0119 (9)
C6	0.0229 (11)	0.0194 (10)	0.0196 (10)	0.0016 (8)	0.0024 (8)	0.0097 (9)
C7	0.0200 (11)	0.0291 (12)	0.0287 (12)	0.0031 (9)	0.0068 (9)	0.0184 (10)
C8	0.0274 (12)	0.0322 (13)	0.0270 (12)	0.0070 (10)	0.0095 (9)	0.0184 (10)
C9	0.0344 (13)	0.0315 (13)	0.0281 (12)	0.0033 (10)	0.0084 (10)	0.0172 (11)
C10	0.0428 (16)	0.0347 (14)	0.0303 (13)	0.0040 (12)	0.0104 (12)	0.0133 (11)
C11	0.0242 (11)	0.0199 (10)	0.0212 (11)	0.0006 (9)	0.0022 (9)	0.0116 (9)
C12	0.0254 (12)	0.0231 (11)	0.0211 (11)	0.0018 (9)	0.0051 (9)	0.0120 (9)
C13	0.0193 (11)	0.0225 (10)	0.0238 (11)	0.0021 (8)	0.0035 (9)	0.0109 (9)
C14	0.0198 (11)	0.0218 (11)	0.0216 (11)	0.0014 (8)	0.0024 (8)	0.0112 (9)
C15	0.0238 (11)	0.0227 (11)	0.0230 (11)	0.0029 (9)	0.0037 (9)	0.0150 (9)
C16	0.0203 (11)	0.0217 (10)	0.0215 (11)	0.0023 (8)	0.0020 (8)	0.0118 (9)
C17	0.0206 (10)	0.0193 (10)	0.0239 (11)	0.0013 (8)	0.0018 (8)	0.0112 (9)
C18	0.0230 (11)	0.0240 (11)	0.0262 (11)	0.0056 (9)	0.0028 (9)	0.0137 (9)
C19	0.0214 (11)	0.0235 (11)	0.0240 (11)	0.0017 (9)	0.0023 (9)	0.0136 (9)
C20	0.0220 (11)	0.0318 (12)	0.0301 (12)	0.0086 (9)	0.0080 (9)	0.0183 (10)
C21	0.0257 (12)	0.0344 (13)	0.0292 (12)	0.0037 (10)	0.0069 (10)	0.0200 (11)
C22	0.0234 (11)	0.0261 (11)	0.0285 (12)	0.0036 (9)	0.0021 (9)	0.0177 (10)
C23	0.0228 (11)	0.0272 (12)	0.0303 (12)	0.0061 (9)	0.0061 (9)	0.0164 (10)
C24	0.0238 (11)	0.0262 (12)	0.0274 (12)	0.0045 (9)	0.0055 (9)	0.0160 (10)
C25	0.0283 (13)	0.0314 (13)	0.0345 (13)	0.0084 (10)	0.0028 (10)	0.0200 (11)
C26	0.0347 (14)	0.0421 (15)	0.0350 (14)	0.0110 (12)	0.0093 (11)	0.0286 (12)

Geometric parameters (Å, º) top

Br1—C3	1.895 (2)	C11—C12	1.386 (3)
Br2—C4	1.895 (2)	C11—C16	1.413 (3)
Br3—C13	1.906 (2)	C12—C13	1.388 (3)
N1—C16	1.382 (3)	C12—H12	0.9500
N1—C1	1.388 (3)	C13—C14	1.423 (3)
N1—C7	1.455 (3)	C14—C15	1.394 (3)
N2—C22	1.378 (3)	C14—C17	1.479 (3)
N2—C26	1.447 (3)	C15—C16	1.389 (3)
N2—C25	1.448 (3)	C15—H15	0.9500
C1—C2	1.390 (3)	C17—C18	1.335 (4)
C1—C6	1.415 (3)	C17—H17	0.9500
C2—C3	1.390 (3)	C18—C19	1.458 (3)
C2—H2	0.9500	C18—H18	0.9500
C3—C4	1.401 (4)	C19—C24	1.398 (3)
C4—C5	1.385 (3)	C19—C20	1.401 (3)
C5—C6	1.393 (3)	C20—C21	1.390 (4)
C5—H5	0.9500	C20—H20	0.9500
C6—C11	1.442 (3)	C21—C22	1.399 (4)
C7—C8	1.530 (4)	C21—H21	0.9500
C7—H7A	0.9900	C22—C23	1.412 (3)
C7—H7B	0.9900	C23—C24	1.379 (3)
C8—C9	1.518 (4)	C23—H23	0.9500
C8—H8A	0.9900	C24—H24	0.9500
C8—H8B	0.9900	C25—H25A	0.9800
C9—C10	1.520 (4)	C25—H25B	0.9800
C9—H9A	0.9900	C25—H25C	0.9800
C9—H9B	0.9900	C26—H26A	0.9800
C10—H10A	0.9800	C26—H26B	0.9800
C10—H10B	0.9800	C26—H26C	0.9800
C10—H10C	0.9800

C16—N1—C1	108.3 (2)	C11—C12—C13	118.5 (2)
C16—N1—C7	124.7 (2)	C11—C12—H12	120.7
C1—N1—C7	126.9 (2)	C13—C12—H12	120.7
C22—N2—C26	120.0 (2)	C12—C13—C14	123.4 (2)
C22—N2—C25	120.1 (2)	C12—C13—Br3	116.64 (18)
C26—N2—C25	119.5 (2)	C14—C13—Br3	119.95 (18)
C2—C1—N1	129.2 (2)	C15—C14—C13	117.0 (2)
C2—C1—C6	121.6 (2)	C15—C14—C17	121.7 (2)
N1—C1—C6	109.1 (2)	C13—C14—C17	121.3 (2)
C1—C2—C3	117.4 (2)	C14—C15—C16	120.1 (2)
C1—C2—H2	121.3	C14—C15—H15	119.9
C3—C2—H2	121.3	C16—C15—H15	119.9
C2—C3—C4	121.7 (2)	N1—C16—C15	128.7 (2)
C2—C3—Br1	117.04 (19)	N1—C16—C11	109.5 (2)
C4—C3—Br1	121.27 (18)	C15—C16—C11	121.8 (2)
C5—C4—C3	120.7 (2)	C18—C17—C14	124.7 (2)
C5—C4—Br2	118.33 (19)	C18—C17—H17	117.7
C3—C4—Br2	120.98 (18)	C14—C17—H17	117.7
C4—C5—C6	118.8 (2)	C17—C18—C19	126.1 (2)
C4—C5—H5	120.6	C17—C18—H18	117.0
C6—C5—H5	120.6	C19—C18—H18	117.0
C5—C6—C1	119.8 (2)	C24—C19—C20	116.7 (2)
C5—C6—C11	133.5 (2)	C24—C19—C18	123.8 (2)
C1—C6—C11	106.6 (2)	C20—C19—C18	119.5 (2)
N1—C7—C8	112.9 (2)	C21—C20—C19	122.3 (2)
N1—C7—H7A	109.0	C21—C20—H20	118.8
C8—C7—H7A	109.0	C19—C20—H20	118.8
N1—C7—H7B	109.0	C20—C21—C22	120.4 (2)
C8—C7—H7B	109.0	C20—C21—H21	119.8
H7A—C7—H7B	107.8	C22—C21—H21	119.8
C9—C8—C7	114.0 (2)	N2—C22—C21	121.7 (2)
C9—C8—H8A	108.8	N2—C22—C23	120.8 (2)
C7—C8—H8A	108.8	C21—C22—C23	117.5 (2)
C9—C8—H8B	108.8	C24—C23—C22	121.3 (2)
C7—C8—H8B	108.8	C24—C23—H23	119.4
H8A—C8—H8B	107.7	C22—C23—H23	119.4
C8—C9—C10	112.2 (2)	C23—C24—C19	121.7 (2)
C8—C9—H9A	109.2	C23—C24—H24	119.1
C10—C9—H9A	109.2	C19—C24—H24	119.1
C8—C9—H9B	109.2	N2—C25—H25A	109.5
C10—C9—H9B	109.2	N2—C25—H25B	109.5
H9A—C9—H9B	107.9	H25A—C25—H25B	109.5
C9—C10—H10A	109.5	N2—C25—H25C	109.5
C9—C10—H10B	109.5	H25A—C25—H25C	109.5
H10A—C10—H10B	109.5	H25B—C25—H25C	109.5
C9—C10—H10C	109.5	N2—C26—H26A	109.5
H10A—C10—H10C	109.5	N2—C26—H26B	109.5
H10B—C10—H10C	109.5	H26A—C26—H26B	109.5
C12—C11—C16	119.2 (2)	N2—C26—H26C	109.5
C12—C11—C6	134.4 (2)	H26A—C26—H26C	109.5
C16—C11—C6	106.4 (2)	H26B—C26—H26C	109.5

C16—N1—C1—C2	−179.3 (2)	C12—C13—C14—C17	178.9 (2)
C7—N1—C1—C2	−2.2 (4)	Br3—C13—C14—C17	−2.1 (3)
C16—N1—C1—C6	0.7 (3)	C13—C14—C15—C16	−0.1 (3)
C7—N1—C1—C6	177.8 (2)	C17—C14—C15—C16	−179.1 (2)
N1—C1—C2—C3	179.8 (2)	C1—N1—C16—C15	180.0 (2)
C6—C1—C2—C3	−0.2 (4)	C7—N1—C16—C15	2.7 (4)
C1—C2—C3—C4	0.2 (4)	C1—N1—C16—C11	−0.6 (3)
C1—C2—C3—Br1	−178.73 (17)	C7—N1—C16—C11	−177.9 (2)
C2—C3—C4—C5	−0.2 (4)	C14—C15—C16—N1	179.8 (2)
Br1—C3—C4—C5	178.67 (18)	C14—C15—C16—C11	0.4 (4)
C2—C3—C4—Br2	−178.20 (19)	C12—C11—C16—N1	180.0 (2)
Br1—C3—C4—Br2	0.6 (3)	C6—C11—C16—N1	0.4 (3)
C3—C4—C5—C6	0.2 (4)	C12—C11—C16—C15	−0.6 (3)
Br2—C4—C5—C6	178.27 (18)	C6—C11—C16—C15	179.8 (2)
C4—C5—C6—C1	−0.2 (4)	C15—C14—C17—C18	−11.2 (4)
C4—C5—C6—C11	−179.3 (2)	C13—C14—C17—C18	169.8 (2)
C2—C1—C6—C5	0.2 (4)	C14—C17—C18—C19	178.0 (2)
N1—C1—C6—C5	−179.8 (2)	C17—C18—C19—C24	6.3 (4)
C2—C1—C6—C11	179.5 (2)	C17—C18—C19—C20	−174.2 (2)
N1—C1—C6—C11	−0.4 (3)	C24—C19—C20—C21	−1.0 (4)
C16—N1—C7—C8	78.0 (3)	C18—C19—C20—C21	179.5 (2)
C1—N1—C7—C8	−98.7 (3)	C19—C20—C21—C22	0.2 (4)
N1—C7—C8—C9	65.2 (3)	C26—N2—C22—C21	1.4 (4)
C7—C8—C9—C10	−175.0 (2)	C25—N2—C22—C21	−171.3 (2)
C5—C6—C11—C12	−0.2 (5)	C26—N2—C22—C23	−177.6 (3)
C1—C6—C11—C12	−179.5 (3)	C25—N2—C22—C23	9.7 (4)
C5—C6—C11—C16	179.3 (3)	C20—C21—C22—N2	−178.0 (3)
C1—C6—C11—C16	0.0 (3)	C20—C21—C22—C23	1.1 (4)
C16—C11—C12—C13	0.4 (3)	N2—C22—C23—C24	177.5 (3)
C6—C11—C12—C13	179.8 (2)	C21—C22—C23—C24	−1.6 (4)
C11—C12—C13—C14	0.0 (4)	C22—C23—C24—C19	0.8 (4)
C11—C12—C13—Br3	−179.05 (17)	C20—C19—C24—C23	0.6 (4)
C12—C13—C14—C15	−0.2 (4)	C18—C19—C24—C23	180.0 (2)
Br3—C13—C14—C15	178.85 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26C···Br1ⁱ	0.98	2.91	3.844 (3)	161

Symmetry code: (i) x+1, y−1, z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₅Br₃N₂
M_r	605.21
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.7304 (3), 11.3834 (4), 11.8197 (4)
α, β, γ (°)	114.308 (3), 101.957 (3), 90.127 (3)
V (Å³)	1161.62 (7)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	6.56
Crystal size (mm)	0.30 × 0.30 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.244, 0.735
No. of measured, independent and observed [I > 2σ(I)] reflections	10766, 4827, 4680
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.092, 1.07
No. of reflections	4827
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.18, −0.81

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26C···Br1ⁱ	0.98	2.91	3.844 (3)	161

Symmetry code: (i) x+1, y−1, z+1.

Footnotes

‡Additional correspondence author: krjt8fcy@iitr.ernet.in.

Acknowledgements

KRJT thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, for financial support [grant No. 01 (2111)/07/EMR-II)]. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM.C/HIR/MOHE/SC/12).

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Lee, W., Cho, N., Kwon, J., Ko, J. & Hong, J.-I. (2012). Chem. Asian J. 7, 343–350. Web of Science CrossRef CAS PubMed Google Scholar
Ooyama, Y., Nagno, T., Inou, S., Imae, I., Komaguchi, K., Ohshita, J. & Harima, Y. (2011). Chem. Eur. J. 17, 14837–14843. Web of Science CrossRef CAS PubMed Google Scholar
Pawluć, P., Franczyk, A., Walkowiak, J., Hreczycho, G., Kubicki, M. & Marciniec, B. (2011). Org. Lett. 13, 1976–1979. Web of Science PubMed Google Scholar
Ramathilagam, C., Venkatesan, N., Rajakumar, P., Umarani, P. R. & Manivannan, V. (2011). Acta Cryst. E67, o2796. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thomas, K. R. J., Lin, J. T., Tao, Y.-T. & Chuan, C.-H. (2004). Chem. Mater. 16, 5437–5444. CAS Google Scholar
Thomas, K. R. J., Lin, J. T., Tao, Y.-T. & Ko, C.-W. (2001). J. Am. Chem. Soc. 123, 9404–9411. Web of Science CSD CrossRef PubMed CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, F.-I., Shih, P.-I., Yuan, M.-C., Dixit, A. K., Shu, C.-F., Chung, Z.-M. & Diau, E. W.-G. (2005). J. Mater. Chem. 15, 4753–4760. Web of Science CrossRef CAS Google Scholar
Zhang, J.-Y. & Zhang, W.-Y. (2011). Acta Cryst. E67, o3307. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1121

doi:10.1107/S1600536812011336

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N,N-Di­methyl-4-[(E)-2-(3,6,7-tri­bromo-9-butyl-9H-carbazol-2-yl)ethen­yl]aniline

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

N,N-Dimethyl-4-[(E)-2-(3,6,7-tribromo-9-butyl-9H-carbazol-2-yl)ethenyl]aniline