9-(4-Bromo­phen­yl)-9H-carbazole

Kautny, P.; Kader, T.; Stöger, B.; Fröhlich, J.

doi:10.1107/S1600536814003705

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o330-o331

doi:10.1107/S1600536814003705

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9-(4-Bromophenyl)-9H-carbazole

Paul Kautny,^a Thomas Kader,^a Berthold Stöger ^b ^* and Johannes Fröhlich ^a

^aInstitute for Applied Synthetic Chemistry, Division Organic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, A-1060 Vienna, Austria, and ^bInstitute for Chemical Technologies and Analytics, Division Structural Chemistry, Vienna University of Technology, Getreidemarkt 9/164-SC, A-1060 Vienna, Austria
^*Correspondence e-mail: bstoeger@mail.tuwien.ac.at

(Received 22 January 2014; accepted 18 February 2014; online 22 February 2014)

In the title molecule, C₁₈H₁₂BrN, the 4-bromophenyl ring is inclined to the mean plane of the carbazole moiety (r.m.s. devation = 0.027 Å) by 49.87 (5)°. In the crystal, molecules stack along [001] and are linked by C—H⋯π interactions forming a corrugated two-dimensional network lying parallel to (100).

CCDC reference: 987662

Related literature

For isostructural crystal structures, see: Saha & Samanta (1999 ); Chen et al. (2005 ). For related carbazole-based crystal structures, see: Kim et al. (2011 ); Liu et al. (2010 ); Wu et al. (2007 ); Chen et al. (2012 ). For a chemically related non-isostructural compound, see: Xie et al. (2012 ). For applications of arylamines as functional materials, see: Shirota & Kageyama (2007 ); Tao et al. (2011 ); Yook & Lee (2012 ); Kautny et al. (2014 ). For isostructurality, see: Kálmán et al. (1999 ). For merotypism and its application to organic compounds, see: Ferraris et al. (2004 ); Stöger et al. (2012 ). For the synthesis of the title compound, see: Xu et al. (2007 ).

Experimental

Crystal data

C₁₈H₁₂BrN
M_r = 322.2
Monoclinic, P 2₁ /c
a = 8.4137 (3) Å
b = 20.1179 (7) Å
c = 8.6346 (3) Å
β = 108.5322 (14)°
V = 1385.76 (8) Å³
Z = 4
Mo Kα radiation
μ = 2.95 mm⁻¹
T = 100 K
0.75 × 0.55 × 0.42 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.16, T_max = 0.29
53140 measured reflections
5056 independent reflections
4340 reflections with I > 3σ(I)
R_int = 0.035

Refinement

R[F² > 3σ(F²)] = 0.031
wR(F) = 0.047
S = 1.69
5056 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg3 and Cg4 are the centroids of the N1/C7/C12/C13/C18, C7–C12 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H1C3⋯Cg3ⁱ	0.96	2.57	3.3237 (14)	135
C5—H1C5⋯Cg4ⁱⁱ	0.96	2.96	3.7527 (15)	141
C14—H1C14⋯Cg1ⁱⁱⁱ	0.96	2.79	3.5367 (14)	135
Symmetry codes: (i) -x+1, -y, -z; (ii) x, y, z-1; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT-Plus (Bruker, 2013); data reduction: SAINT-Plus; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ); molecular graphics: ATOMS (Dowty, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 987662

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814003705/kj2237sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814003705/kj2237Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814003705/kj2237Isup3.cml

checkCIF report

Comment top

Arylamines are widely used as electron donors in functional organic materials (Shirota & Kageyama, 2007; Tao et al., 2011; Yook & Lee, 2012). In our recent work we investigated the effect of increasingly planarized triarylamine donors (from N,N-diphenylbenzenamine to 9-phenyl-9H-carbazole and indolo[3,2,1-jk]carbazole) on material properties of bipolar compounds (Kautny et al., 2014). Thus, the title compound 9-(4-bromophenyl)-9H-carbazole (I) was synthesized as a key intermediate towards materials incorporating 9-phenyl-9H-carbazole donor subunits.

(I) crystallizes in the space group P2₁/c with one molecule (Fig. 1) in the asymmetric unit. The molecules are arranged in distinct crystallo-chemical layers parallel to (010). The layers contact via the carbazoles (Fig. 2 (a,b)). The contacting carbazoles are strongly inclined to each other [angle between least squares (l.s.) plane 59.08°], thus π-π interactions can be ruled out. The phenyl rings inside the layers are related by inversion and therefore coplanar. Nevertheless, the rings do not overlap, excluding π-π interactions (Fig. 2(b)).

Two structures that can be considered as isostructural (Kálmán et al., 1999) with (I) have been described, viz. the analogues with Br substituted by the pseudo-halogenide CN (Saha and Samanta, 1999) or by a NO₂ group (Chen et al., 2005). A second polymorph of the CN analogue is structurally unrelated (Xie et al., 2012). In all three isostructural crystals the benzene ring is strongly inclined with respect to the carbazole moiety [angles between l.s. planes of both aromatic systems: (I): 49.87 (5)°; CN: 47.89 (6)°; NO₂: 53.08 (6)°]. The inclination of the carbazole and phenyl moieties is of particular interest, since it determines the overall degree of conjugation and therefore greatly influences the electro-chemical and photo-physical properties of bipolar materials (Tao et al., 2011).

Several structures with distinctly more bulky substituents on the para-position of the phenyl ring have been described which nevertheless feature a virtually identical arrangement of the carbazole rings as observed in (I). Thus, it is useful to ,,slice'' the crystal structure of (I) into two kinds of slabs parallel to (010) which do not correspond to layers in the crystallo-chemical sense as depicted in Fig. 1. The slabs designated as A are made up of the carbazole rings of two adjacent crystallo-chemical layers (Fig. 3(a)), whereas the B slabs are composed of the 4-bromophenyl moieties (Fig. 3(b)). The A and B slabs feature p1(c)1 (the parentheses mark the direction missing translational symmetry) and p1 layer symmetry, respectively. Examples of structures which feature isostructural A slabs and structurally unrelated B slabs are 2-(4-(9H-carbazol-9-yl)benzylidene)indan-1-one (Fig. 4(a)) (Kim et al., 2011), 9-(4-((4-methylphenyl)ethynyl)phenyl)-9H-carbazole (Fig. 4(b)) and the isostructural 4-bromophenyl analogue (Fig. 4(c)) (Liu et al., 2010), the mono-toluene solvate of 3-(4-(9H-carbazol-9-yl)phenyl)acrylic acid (Fig. 4(d)) (Wu et al., 2007) and 9-(4-(2-(4-(2,1,3-benzothiadiazol-4-ylethynyl)phenyl)vinyl)phenyl)-9H-carbazole (Fig. 4(e)) (Chen, et al., 2012). The crystal structure of the latter is depicted in Fig. 5 and a comparison of the A slabs to those in (I) is given in Fig. 3(c). Despite being structurally unrelated, the B slabs in all these structures feature, like the corresponding slab in (I), p1 symmetry. Therefore, these structures possess likewise overall P2₁/c space group symmetry. In the crystal chemistry of inorganic compounds, the A and B slabs are called modules and the structures given above can be considered as members of a merotypic series (Ferraris et al., 2004). Whereas describing crystal structures of organic molecules in terms of modular materials is uncommon, we have recently applied these concepts to the solvatomorphs of a carbazole based organic molecule related to (I) (Stöger et al., 2012).

Related literature top

For isostructural crystal structures, see: Saha & Samanta (1999); Chen et al. (2005). For related carbazole-based crystal structures, see: Kim et al. (2011); Liu et al. (2010); Wu et al. (2007); Chen et al. (2012). For a chemically related non-isostructural compound, see: Xie et al. (2012). For applications of arylamines as functional materials, see: Shirota & Kageyama (2007); Tao et al. (2011); Yook & Lee (2012); Kautny et al. (2014). For isostructurality, see: Kálmán et al. (1999). For merotypism and its application to organic compounds, see: Ferraris et al. (2004); Stöger et al. (2012). For the synthesis of the title compound, see: Xu et al. (2007).

Experimental top

The synthesis of (I) was performed according to the procedure described by Xu et al. (2007). A fused silica ampoule was charged with 9H-carbazole (5.35 g, 32.0 mmol, 1.00 eq.), 1,4-dibromobenzene (9.06 g, 38.4 mmol, 1.20 eq.), CuSO₄·5H₂O (400 mg, 1.6 mmol, 0.05 eq.) and K₂CO₃ (4.42 g, 32.0 mmol, 1.00 eq.) The sealed ampoule was heated to 250 °C for 68 h. After cooling, the tube was carefully opened with a diamond blade, releasing a small amount of gas. The solid residue was partitioned between toluene and water and the aqueous phase was extracted with toluene. The combined organic layers were washed with water, dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. Purification was performed by column chromatography (light petroleum:DCM 75:25) yielding 9-(4-bromophenyl)-9H-carbazole (4.22 g, 13.1 mmol, 41%) as white solid. Large single crystals of (I) were grown by slow evaporation of a CDCl₃ solution.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT-Plus (Bruker, 2013); data reduction: SAINT-Plus (Bruker, 2013); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: ATOMS (Dowty, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I). C, N and Br are represented by grey, blue and green ellipsoids drawn at the 75% probability levels, H atoms by white spheres of arbitrary radius.
	Fig. 2. Crystal structure of (I) viewed down (a) [100] and (b) [001]. C, N and Br atoms are represented by spheres of arbitrary radius. H atoms were omitted for clarity. Colour codes as in Fig. 1. The position of the crystallo-chemical layers is indicated to the left, the position of the A and B slabs to the right
	Fig. 3. The (a) A and (b) B slabs of (I) composed of 9H-carbazol-9-yl and 4-bromophenyl fragments, respectively projected on (001). (c) The A slabs in 9-(4-(2-(4-(2,1,3-benzothiadiazol-4-ylethynyl)phenyl)vinyl)phenyl)-9H-carbazole (coordinates from Chen, et al., (2012)). Colour codes as in Fig. 1.
	Fig. 4. 4-(9H-carbazol-9-yl)-phenyl derivatives crystallizing with A slabs isotypic to (I).
	Fig. 5. The crystal structure of 9-(4-(2-(4-(2,1,3-benzothiadiazol-4-ylethynyl)phenyl)vinyl)phenyl)-9H-carbazole. S atoms are yellow, other colour codes as in Fig. 1.

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

Crystal data top

C₁₈H₁₂BrN	F(000) = 648
M_r = 322.2	D_x = 1.544 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycb	Cell parameters from 25237 reflections
a = 8.4137 (3) Å	θ = 2.5–32.5°
b = 20.1179 (7) Å	µ = 2.95 mm⁻¹
c = 8.6346 (3) Å	T = 100 K
β = 108.5322 (14)°	Block, clear colourless
V = 1385.76 (8) Å³	0.75 × 0.55 × 0.42 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	5056 independent reflections
Radiation source: X-ray tube	4340 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.035
ω and φ scans	θ_max = 32.8°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −12→12
T_min = 0.16, T_max = 0.29	k = −30→30
53140 measured reflections	l = −13→13

Refinement top

Refinement on F	Primary atom site location: iterative
R[F² > 2σ(F²)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.047	H-atom parameters constrained
S = 1.69	Weighting scheme based on measured s.u.'s w = 1/(σ²(F) + 0.0004F²)
5056 reflections	(Δ/σ)_max = 0.026
181 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³
48 constraints

Crystal data top

C₁₈H₁₂BrN	V = 1385.76 (8) Å³
M_r = 322.2	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4137 (3) Å	µ = 2.95 mm⁻¹
b = 20.1179 (7) Å	T = 100 K
c = 8.6346 (3) Å	0.75 × 0.55 × 0.42 mm
β = 108.5322 (14)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5056 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	4340 reflections with I > 3σ(I)
T_min = 0.16, T_max = 0.29	R_int = 0.035
53140 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.047	H-atom parameters constrained
S = 1.69	Δρ_max = 0.47 e Å⁻³
5056 reflections	Δρ_min = −0.51 e Å⁻³
181 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.84651 (2)	−0.036314 (8)	−0.405902 (18)	0.02427 (6)
N1	0.51185 (14)	0.12342 (5)	0.00001 (13)	0.0116 (3)
C1	0.58687 (16)	0.08548 (6)	−0.09658 (15)	0.0111 (3)
C2	0.69269 (18)	0.03277 (6)	−0.02622 (17)	0.0133 (4)
C3	0.77018 (17)	−0.00373 (6)	−0.11813 (17)	0.0139 (4)
C4	0.73532 (17)	0.01171 (7)	−0.28261 (16)	0.0139 (4)
C5	0.62817 (17)	0.06309 (7)	−0.35594 (16)	0.0148 (4)
C6	0.55565 (17)	0.10094 (7)	−0.26077 (15)	0.0135 (3)
C7	0.34167 (16)	0.13791 (6)	−0.03947 (16)	0.0118 (3)
C8	0.21016 (17)	0.12051 (7)	−0.17824 (16)	0.0147 (4)
C9	0.04953 (18)	0.13772 (7)	−0.18154 (18)	0.0174 (4)
C10	0.01993 (18)	0.17175 (7)	−0.05191 (19)	0.0190 (4)
C11	0.15091 (18)	0.18942 (7)	0.08536 (18)	0.0172 (4)
C12	0.31464 (17)	0.17212 (6)	0.09265 (16)	0.0127 (4)
C13	0.47576 (17)	0.17913 (6)	0.21673 (16)	0.0122 (3)
C14	0.52962 (19)	0.20908 (6)	0.37103 (17)	0.0164 (4)
C15	0.6979 (2)	0.20772 (7)	0.46009 (17)	0.0186 (4)
C16	0.81376 (18)	0.17722 (7)	0.39656 (17)	0.0168 (4)
C17	0.76424 (17)	0.14676 (6)	0.24474 (16)	0.0143 (4)
C18	0.59415 (16)	0.14789 (6)	0.15611 (15)	0.0116 (3)
H1c2	0.712034	0.021682	0.086423	0.016*
H1c3	0.846464	−0.038992	−0.069149	0.0167*
H1c5	0.604265	0.072462	−0.470097	0.0178*
H1c6	0.484129	0.13771	−0.308549	0.0162*
H1c8	0.229898	0.097553	−0.267885	0.0176*
H1c9	−0.043798	0.125999	−0.275106	0.0208*
H1c10	−0.092883	0.182992	−0.058358	0.0228*
H1c11	0.130161	0.212998	0.17367	0.0206*
H1c14	0.450589	0.230279	0.414296	0.0197*
H1c15	0.735971	0.227799	0.566404	0.0223*
H1c16	0.930439	0.177463	0.459918	0.0202*
H1c17	0.844122	0.125706	0.202336	0.0172*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02113 (9)	0.03450 (10)	0.02083 (9)	0.00656 (6)	0.01183 (6)	−0.00729 (6)
N1	0.0095 (5)	0.0143 (5)	0.0113 (4)	0.0012 (4)	0.0040 (4)	−0.0020 (4)
C1	0.0106 (5)	0.0134 (5)	0.0109 (5)	−0.0005 (4)	0.0055 (4)	−0.0013 (4)
C2	0.0139 (6)	0.0133 (5)	0.0145 (6)	−0.0009 (4)	0.0069 (5)	0.0000 (4)
C3	0.0127 (6)	0.0132 (5)	0.0174 (6)	0.0004 (4)	0.0071 (5)	−0.0009 (4)
C4	0.0121 (5)	0.0173 (6)	0.0148 (5)	−0.0017 (5)	0.0079 (5)	−0.0046 (5)
C5	0.0147 (6)	0.0199 (6)	0.0116 (5)	−0.0005 (5)	0.0066 (5)	−0.0015 (5)
C6	0.0125 (5)	0.0166 (6)	0.0120 (5)	0.0007 (4)	0.0047 (4)	0.0003 (4)
C7	0.0105 (5)	0.0114 (5)	0.0147 (5)	0.0016 (4)	0.0059 (4)	0.0011 (4)
C8	0.0128 (6)	0.0167 (6)	0.0145 (5)	0.0000 (4)	0.0042 (4)	0.0010 (4)
C9	0.0126 (6)	0.0192 (6)	0.0192 (6)	0.0008 (5)	0.0034 (5)	0.0048 (5)
C10	0.0130 (6)	0.0174 (6)	0.0286 (7)	0.0043 (5)	0.0094 (5)	0.0044 (5)
C11	0.0167 (6)	0.0140 (6)	0.0249 (7)	0.0037 (5)	0.0123 (5)	0.0008 (5)
C12	0.0134 (5)	0.0105 (5)	0.0161 (6)	0.0016 (4)	0.0073 (5)	0.0008 (4)
C13	0.0157 (6)	0.0091 (5)	0.0135 (5)	0.0001 (4)	0.0071 (4)	−0.0005 (4)
C14	0.0222 (7)	0.0117 (5)	0.0172 (6)	0.0004 (5)	0.0090 (5)	−0.0034 (4)
C15	0.0260 (7)	0.0148 (6)	0.0140 (6)	−0.0028 (5)	0.0051 (5)	−0.0039 (5)
C16	0.0181 (6)	0.0151 (6)	0.0158 (6)	−0.0031 (5)	0.0033 (5)	−0.0003 (5)
C17	0.0139 (6)	0.0147 (5)	0.0144 (5)	0.0000 (4)	0.0046 (5)	−0.0003 (4)
C18	0.0133 (5)	0.0109 (5)	0.0113 (5)	−0.0007 (4)	0.0051 (4)	−0.0011 (4)

Geometric parameters (Å, º) top

Br1—C4	1.8909 (15)	C9—C10	1.400 (2)
N1—C1	1.4182 (19)	C9—H1c9	0.96
N1—C7	1.3932 (17)	C10—C11	1.3840 (18)
N1—C18	1.3947 (15)	C10—H1c10	0.96
C1—C2	1.3937 (17)	C11—C12	1.403 (2)
C1—C6	1.3925 (18)	C11—H1c11	0.96
C2—C3	1.387 (2)	C12—C13	1.4430 (17)
C2—H1c2	0.96	C13—C14	1.3999 (18)
C3—C4	1.3910 (19)	C13—C18	1.412 (2)
C3—H1c3	0.96	C14—C15	1.380 (2)
C4—C5	1.3853 (18)	C14—H1c14	0.96
C5—C6	1.395 (2)	C15—C16	1.403 (2)
C5—H1c5	0.96	C15—H1c15	0.96
C6—H1c6	0.96	C16—C17	1.3858 (19)
C7—C8	1.3928 (16)	C16—H1c16	0.96
C7—C12	1.411 (2)	C17—C18	1.3922 (18)
C8—C9	1.387 (2)	C17—H1c17	0.96
C8—H1c8	0.96

C1—N1—C7	125.70 (10)	C10—C9—H1c9	119.15
C1—N1—C18	125.54 (11)	C9—C10—C11	120.97 (14)
C7—N1—C18	108.58 (12)	C9—C10—H1c10	119.51
N1—C1—C2	119.68 (12)	C11—C10—H1c10	119.51
N1—C1—C6	120.22 (11)	C10—C11—C12	118.56 (14)
C2—C1—C6	120.10 (13)	C10—C11—H1c11	120.72
C1—C2—C3	120.32 (13)	C12—C11—H1c11	120.72
C1—C2—H1c2	119.84	C7—C12—C11	119.54 (11)
C3—C2—H1c2	119.84	C7—C12—C13	107.05 (12)
C2—C3—C4	118.76 (12)	C11—C12—C13	133.35 (13)
C2—C3—H1c3	120.62	C12—C13—C14	133.82 (14)
C4—C3—H1c3	120.62	C12—C13—C18	106.75 (11)
Br1—C4—C3	118.63 (10)	C14—C13—C18	119.43 (12)
Br1—C4—C5	119.37 (11)	C13—C14—C15	119.10 (15)
C3—C4—C5	121.92 (14)	C13—C14—H1c14	120.45
C4—C5—C6	118.75 (12)	C15—C14—H1c14	120.45
C4—C5—H1c5	120.62	C14—C15—C16	120.54 (13)
C6—C5—H1c5	120.63	C14—C15—H1c15	119.73
C1—C6—C5	120.10 (12)	C16—C15—H1c15	119.73
C1—C6—H1c6	119.95	C15—C16—C17	121.73 (12)
C5—C6—H1c6	119.95	C15—C16—H1c16	119.13
N1—C7—C8	129.17 (13)	C17—C16—H1c16	119.13
N1—C7—C12	108.74 (10)	C16—C17—C18	117.40 (14)
C8—C7—C12	122.00 (13)	C16—C17—H1c17	121.3
C7—C8—C9	117.23 (13)	C18—C17—H1c17	121.3
C7—C8—H1c8	121.39	N1—C18—C13	108.87 (11)
C9—C8—H1c8	121.39	N1—C18—C17	129.30 (14)
C8—C9—C10	121.70 (12)	C13—C18—C17	121.78 (12)
C8—C9—H1c9	119.15

Hydrogen-bond geometry (Å, º) top

Cg1, Cg3 and Cg4 are the centroids of the N1/C7/C12/C13/C18, C7–C12 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H1C3···Cg3ⁱ	0.96	2.57	3.3237 (14)	135
C5—H1C5···Cg4ⁱⁱ	0.96	2.96	3.7527 (15)	141
C14—H1C14···Cg1ⁱⁱⁱ	0.96	2.79	3.5367 (14)	135

Symmetry codes: (i) −x+1, −y, −z; (ii) x, y, z−1; (iii) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg1, Cg3 and Cg4 are the centroids of the N1/C7/C12/C13/C18, C7–C12 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H1C3···Cg3ⁱ	0.96	2.57	3.3237 (14)	135
C5—H1C5···Cg4ⁱⁱ	0.96	2.96	3.7527 (15)	141
C14—H1C14···Cg1ⁱⁱⁱ	0.96	2.79	3.5367 (14)	135

Symmetry codes: (i) −x+1, −y, −z; (ii) x, y, z−1; (iii) x, −y+1/2, z+1/2.

Acknowledgements

The X-ray centre (XRC) of the Vienna University of Technology is acknowledged for providing access to the single-crystal diffractometer and for financial support.

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Volume 70| Part 3| March 2014| Pages o330-o331

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