1-(1H-Benzimidazol-1-ylmeth-yl)-3-[2-(di-isopropyl-amino)eth-yl]-1H-benzimid-azolium bromide 0.25-hydrate.

The title N-heterocyclic carbene derivative, C(23)H(30)N(5) (+)·Br(-)·0.25H(2)O, was synthesized using microwave heating and was characterized by (1)H and (13)C NMR spectroscopy and a single-crystal X-ray diffraction study. The structure of the title compound are stabilized by a network of intra- and inter-molecular C-H⋯Br hydrogen-bonding inter-actions. The crystal structure is further stabilized by π-π stacking inter-actions between benzene and imidazole fragment rings of parallel benzo[d]imidazole rings, with a separation of 3.486 (3) Å between the centroids of the benzene and imidazole rings. There is also an inter-molecular C-H⋯π inter-action in the crystal structure. The C-N bond lengths for the central benzimidazole ring are shorter than the average single C-N bond, thus showing varying degrees of double-bond character and indicating partial electron delocalization within the C-N-C-N-C fragment. The isopropyl group is disordered over two sites with occupancies of 0.792 (10) and 0.208 (10).

Related literature

For the synthesis, see: Yaşar et al. (2008 ▶). For general background, see: Herrmann et al. (1995 ▶); Navarro et al. (2006 ▶); Arduengo & Krafczyc (1998 ▶); Larhed et al. (2002 ▶); Leadbeater & Shoemaker (2008 ▶). For related compounds, see: Özel Güven et al. (2008a ▶,b ▶,c ▶); Türktekin et al. (2004 ▶); Akkurt et al. (2004 ▶, 2005 ▶, 2007a ▶,b ▶); Arslan et al. (2005 ▶, 2007 ▶, 2009 ▶ and references therein).

Experimental

Crystal data

C23H30N5 +·Br−·0.25H2O

M = 460.93

Triclinic,

a = 8.4944 (17) Å

b = 9.4960 (19) Å

c = 15.318 (3) Å

α = 83.29 (3)°

β = 84.69 (3)°

γ = 65.93 (3)°

V = 1119.1 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.86 mm−1

T = 153 K

0.34 × 0.12 × 0.10 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.571, T max = 0.836

7638 measured reflections

3889 independent reflections

2390 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.144

S = 0.98

3889 reflections

282 parameters

22 restraints

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.71 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900765X/hg2484sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900765X/hg2484Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H30N5+·Br−·0.25H2O	Z = 2
Mr = 460.93	F(000) = 481
Triclinic, P1	Dx = 1.368 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4944 (17) Å	Cell parameters from 5869 reflections
b = 9.4960 (19) Å	θ = 3.2–26.4°
c = 15.318 (3) Å	µ = 1.86 mm−1
α = 83.29 (3)°	T = 153 K
β = 84.69 (3)°	Rod, colorless
γ = 65.93 (3)°	0.34 × 0.12 × 0.10 mm
V = 1119.1 (5) Å3

Rigaku Mercury CCD diffractometer	3889 independent reflections
Radiation source: Sealed Tube	2390 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.039
Detector resolution: 14.6306 pixels mm-1	θmax = 25.0°, θmin = 3.2°
ω scans	h = −9→10
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −11→11
Tmin = 0.571, Tmax = 0.836	l = −17→18
7638 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0659P)2] where P = (Fo2 + 2Fc2)/3
3889 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 0.74 e Å−3
22 restraints	Δρmin = −0.71 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.78369 (7)	0.88546 (6)	0.57962 (4)	0.05288 (19)
N1	0.6315 (5)	0.5169 (5)	0.6422 (2)	0.0430 (10)
N2	0.3772 (6)	0.7103 (4)	0.6314 (3)	0.0499 (11)
N3	0.1831 (7)	0.9149 (5)	0.7189 (3)	0.0544 (12)
N4	0.0314 (6)	0.9404 (5)	0.8478 (3)	0.0575 (12)
N5	0.7558 (5)	0.4797 (5)	0.8187 (2)	0.0411 (10)
C1	0.5416 (8)	0.6676 (6)	0.6495 (3)	0.0511 (14)
H1	0.5890	0.7364	0.6658	0.061*
C2	0.5188 (6)	0.4562 (5)	0.6178 (3)	0.0334 (10)
C3	0.5464 (6)	0.3083 (5)	0.5999 (3)	0.0352 (10)
H3	0.6568	0.2231	0.6057	0.042*
C4	0.4050 (6)	0.2909 (5)	0.5732 (3)	0.0375 (11)
H4	0.4179	0.1906	0.5595	0.045*
C5	0.2451 (6)	0.4136 (5)	0.5654 (3)	0.0416 (12)
H5	0.1508	0.3949	0.5470	0.050*
C6	0.2162 (7)	0.5628 (6)	0.5833 (3)	0.0475 (13)
H6	0.1060	0.6480	0.5770	0.057*
C7	0.3565 (7)	0.5795 (5)	0.6106 (3)	0.0382 (11)
C8	0.2416 (10)	0.8685 (6)	0.6319 (4)	0.0700 (18)
H8A	0.2855	0.9397	0.6007	0.084*
H8B	0.1452	0.8743	0.6013	0.084*
C9	0.0487 (8)	0.8983 (6)	0.7688 (4)	0.0629 (17)
H9	−0.0264	0.8588	0.7471	0.075*
C11	0.1667 (7)	0.9865 (5)	0.8532 (3)	0.0416 (12)
C12	0.2084 (7)	1.0432 (5)	0.9234 (3)	0.0470 (13)
H12	0.1438	1.0529	0.9788	0.056*
C13	0.3479 (9)	1.0850 (7)	0.9095 (4)	0.0683 (17)
H13	0.3776	1.1281	0.9559	0.082*
C14	0.4463 (10)	1.0666 (8)	0.8304 (5)	0.091 (2)
H14	0.5443	1.0937	0.8245	0.109*
C15	0.4059 (9)	1.0098 (7)	0.7597 (4)	0.078 (2)
H15	0.4722	0.9984	0.7047	0.093*
C16	0.2652 (8)	0.9710 (5)	0.7730 (3)	0.0497 (14)
C17	0.8119 (6)	0.4275 (7)	0.6628 (3)	0.0518 (14)
H17A	0.8739	0.4932	0.6528	0.062*
H17B	0.8634	0.3453	0.6247	0.062*
C18	0.8254 (7)	0.3596 (6)	0.7583 (3)	0.0461 (13)
H18A	0.7636	0.2936	0.7680	0.055*
H18B	0.9444	0.2974	0.7696	0.055*
C19	0.6381 (6)	0.4499 (5)	0.8896 (3)	0.0348 (10)
H19	0.6113	0.5273	0.9302	0.042*
C20	0.4689 (6)	0.4737 (6)	0.8519 (3)	0.0462 (12)
H20A	0.4186	0.5761	0.8229	0.069*
H20B	0.3911	0.4610	0.8986	0.069*
H20C	0.4903	0.3989	0.8103	0.069*
C21	0.7152 (7)	0.2931 (6)	0.9424 (3)	0.0489 (13)
H21A	0.7476	0.2122	0.9037	0.073*
H21B	0.6313	0.2831	0.9864	0.073*
H21C	0.8153	0.2852	0.9705	0.073*
C22	0.9092 (11)	0.5022 (9)	0.8612 (5)	0.054 (2)	0.792 (10)
H22	0.9695	0.4146	0.9013	0.065*	0.792 (10)
C22'	0.843 (2)	0.582 (2)	0.8331 (14)	0.021 (5)*	0.208 (10)
H22'	0.9455	0.5571	0.8048	0.025*	0.208 (10)
C23	1.0298 (9)	0.5239 (10)	0.7878 (5)	0.098 (2)
H23A	1.1470	0.4660	0.8038	0.118*
H23B	1.0083	0.6318	0.7774	0.118*
H23C	1.0110	0.4880	0.7353	0.118*
C24	0.8241 (13)	0.6470 (11)	0.9089 (6)	0.090 (3)	0.792 (10)
H24A	0.7210	0.7156	0.8803	0.136*	0.792 (10)
H24B	0.9019	0.6974	0.9079	0.136*	0.792 (10)
H24C	0.7950	0.6202	0.9687	0.136*	0.792 (10)
C24'	0.729 (2)	0.726 (2)	0.8681 (14)	0.022 (5)*	0.208 (10)
H24D	0.6329	0.7782	0.8312	0.034*	0.208 (10)
H24E	0.7908	0.7908	0.8697	0.034*	0.208 (10)
H24F	0.6878	0.7052	0.9265	0.034*	0.208 (10)
O1	0.968 (2)	0.133 (2)	0.5686 (12)	0.076 (5)	0.25

	U11	U22	U33	U12	U13	U23
Br1	0.0484 (3)	0.0364 (3)	0.0800 (4)	−0.0213 (2)	−0.0238 (3)	0.0042 (2)
N1	0.061 (2)	0.061 (3)	0.024 (2)	−0.042 (2)	0.0074 (18)	−0.0127 (18)
N2	0.093 (3)	0.030 (2)	0.028 (2)	−0.025 (2)	−0.002 (2)	−0.0085 (18)
N3	0.097 (4)	0.031 (2)	0.030 (2)	−0.017 (2)	−0.011 (2)	−0.0116 (18)
N4	0.054 (3)	0.050 (3)	0.068 (3)	−0.015 (2)	−0.003 (2)	−0.027 (2)
N5	0.058 (2)	0.051 (2)	0.026 (2)	−0.033 (2)	0.0081 (18)	−0.0133 (18)
C1	0.097 (4)	0.051 (3)	0.026 (3)	−0.050 (3)	0.006 (3)	−0.011 (2)
C2	0.045 (2)	0.038 (3)	0.025 (2)	−0.025 (2)	0.007 (2)	−0.0089 (19)
C3	0.042 (2)	0.035 (2)	0.030 (3)	−0.017 (2)	0.004 (2)	−0.008 (2)
C4	0.051 (3)	0.036 (3)	0.032 (3)	−0.023 (2)	0.000 (2)	−0.009 (2)
C5	0.041 (3)	0.044 (3)	0.041 (3)	−0.016 (2)	−0.002 (2)	−0.012 (2)
C6	0.053 (3)	0.046 (3)	0.028 (3)	−0.002 (3)	−0.003 (2)	−0.014 (2)
C7	0.064 (3)	0.034 (3)	0.019 (2)	−0.020 (2)	−0.002 (2)	−0.0061 (19)
C8	0.128 (5)	0.032 (3)	0.038 (3)	−0.017 (3)	−0.014 (3)	−0.004 (2)
C9	0.057 (3)	0.048 (3)	0.077 (5)	−0.006 (3)	−0.009 (3)	−0.032 (3)
C11	0.058 (3)	0.027 (2)	0.036 (3)	−0.012 (2)	−0.003 (2)	−0.005 (2)
C12	0.068 (3)	0.034 (3)	0.035 (3)	−0.015 (3)	−0.005 (3)	−0.006 (2)
C13	0.100 (5)	0.065 (4)	0.055 (4)	−0.042 (4)	0.002 (3)	−0.033 (3)
C14	0.129 (5)	0.098 (5)	0.088 (5)	−0.088 (4)	0.046 (4)	−0.058 (4)
C15	0.145 (5)	0.067 (4)	0.053 (4)	−0.078 (4)	0.041 (4)	−0.031 (3)
C16	0.097 (4)	0.027 (3)	0.031 (3)	−0.029 (3)	−0.004 (3)	−0.009 (2)
C17	0.054 (3)	0.081 (4)	0.041 (3)	−0.047 (3)	0.014 (2)	−0.024 (3)
C18	0.048 (3)	0.057 (3)	0.036 (3)	−0.022 (3)	0.011 (2)	−0.019 (2)
C19	0.038 (2)	0.040 (3)	0.026 (2)	−0.014 (2)	0.0014 (19)	−0.004 (2)
C20	0.047 (3)	0.060 (3)	0.036 (3)	−0.025 (3)	−0.002 (2)	−0.002 (2)
C21	0.051 (3)	0.044 (3)	0.044 (3)	−0.014 (3)	0.000 (2)	0.006 (2)
C22	0.092 (5)	0.050 (4)	0.035 (4)	−0.047 (4)	0.021 (4)	−0.008 (3)
C23	0.076 (4)	0.142 (6)	0.109 (6)	−0.067 (5)	−0.014 (4)	−0.037 (5)
C24	0.131 (7)	0.119 (7)	0.075 (6)	−0.100 (6)	0.029 (6)	−0.053 (5)
O1	0.070 (10)	0.081 (11)	0.091 (13)	−0.040 (9)	0.006 (9)	−0.027 (10)

N1—C1	1.332 (6)	C14—C15	1.392 (8)
N1—C2	1.399 (5)	C14—H14	0.9600
N1—C17	1.461 (7)	C15—C16	1.379 (8)
N2—C1	1.333 (7)	C15—H15	0.9600
N2—C7	1.398 (5)	C17—C18	1.522 (7)
N2—C8	1.474 (7)	C17—H17A	0.9600
N3—C9	1.367 (7)	C17—H17B	0.9600
N3—C16	1.404 (6)	C18—H18A	0.9600
N3—C8	1.432 (7)	C18—H18B	0.9600
N4—C9	1.296 (7)	C19—C20	1.519 (6)
N4—C11	1.399 (6)	C19—C21	1.524 (7)
N5—C18	1.450 (6)	C19—H19	0.9600
N5—C22'	1.487 (19)	C20—H20A	0.9599
N5—C19	1.489 (5)	C20—H20B	0.9599
N5—C22	1.608 (8)	C20—H20C	0.9599
C1—H1	0.9600	C21—H21A	0.9599
C2—C3	1.382 (6)	C21—H21B	0.9599
C2—C7	1.402 (7)	C21—H21C	0.9599
C3—C4	1.380 (6)	C22—C23	1.504 (9)
C3—H3	0.9600	C22—C24	1.507 (10)
C4—C5	1.387 (6)	C22—H22	0.9600
C4—H4	0.9600	C22—H22'	1.045 (6)
C5—C6	1.393 (6)	C22'—C24'	1.44 (2)
C5—H5	0.9600	C22'—H22'	0.889 (17)
C6—C7	1.372 (7)	C23—H22'	0.693 (7)
C6—H6	0.9600	C23—H23A	0.9600
C8—H8A	0.9600	C23—H23B	0.9600
C8—H8B	0.9600	C23—H23C	0.9600
C9—H9	0.9600	C24—H24A	0.9600
C11—C12	1.391 (7)	C24—H24B	0.9600
C11—C16	1.407 (7)	C24—H24C	0.9600
C12—C13	1.387 (8)	C24'—H24D	0.9600
C12—H12	0.9600	C24'—H24E	0.9600
C13—C14	1.392 (8)	C24'—H24F	0.9600
C13—H13	0.9600
C1—N1—C2	107.8 (4)	C15—C16—N3	133.2 (5)
C1—N1—C17	126.4 (4)	C15—C16—C11	122.7 (5)
C2—N1—C17	125.6 (4)	N3—C16—C11	104.0 (5)
C1—N2—C7	108.1 (4)	N1—C17—C18	110.7 (4)
C1—N2—C8	125.8 (5)	N1—C17—H17A	109.5
C7—N2—C8	126.1 (5)	C18—C17—H17A	109.5
C9—N3—C16	106.5 (4)	N1—C17—H17B	109.5
C9—N3—C8	127.1 (5)	C18—C17—H17B	109.5
C16—N3—C8	126.1 (5)	H17A—C17—H17B	108.1
C9—N4—C11	104.7 (5)	N5—C18—C17	111.7 (4)
C18—N5—C22'	123.0 (8)	N5—C18—H18A	109.3
C18—N5—C19	113.1 (3)	C17—C18—H18A	109.3
C22'—N5—C19	119.4 (8)	N5—C18—H18B	109.3
C18—N5—C22	110.5 (4)	C17—C18—H18B	109.3
C19—N5—C22	109.9 (3)	H18A—C18—H18B	108.0
N1—C1—N2	111.1 (4)	N5—C19—C20	110.0 (4)
N1—C1—H1	124.5	N5—C19—C21	114.8 (4)
N2—C1—H1	124.5	C20—C19—C21	111.1 (4)
C3—C2—N1	131.3 (4)	N5—C19—H19	106.8
C3—C2—C7	121.9 (4)	C20—C19—H19	106.8
N1—C2—C7	106.8 (4)	C21—C19—H19	106.8
C4—C3—C2	115.7 (4)	C19—C20—H20A	109.5
C4—C3—H3	122.1	C19—C20—H20B	109.5
C2—C3—H3	122.1	H20A—C20—H20B	109.5
C3—C4—C5	122.2 (4)	C19—C20—H20C	109.5
C3—C4—H4	118.9	H20A—C20—H20C	109.5
C5—C4—H4	118.9	H20B—C20—H20C	109.5
C4—C5—C6	122.4 (4)	C19—C21—H21A	109.5
C4—C5—H5	118.8	C19—C21—H21B	109.5
C6—C5—H5	118.8	H21A—C21—H21B	109.5
C7—C6—C5	115.3 (5)	C19—C21—H21C	109.5
C7—C6—H6	122.4	H21A—C21—H21C	109.5
C5—C6—H6	122.4	H21B—C21—H21C	109.5
C6—C7—N2	131.2 (5)	C23—C22—C24	110.2 (6)
C6—C7—C2	122.5 (4)	C23—C22—N5	108.3 (5)
N2—C7—C2	106.3 (4)	C24—C22—N5	105.8 (6)
N3—C8—N2	113.0 (4)	C23—C22—H22	110.8
N3—C8—H8A	109.0	C24—C22—H22	110.8
N2—C8—H8A	109.0	N5—C22—H22	110.8
N3—C8—H8B	109.0	C24'—C22'—N5	114.1 (14)
N2—C8—H8B	109.0	N5—C22'—H22'	113.3 (17)
H8A—C8—H8B	107.8	C22—C23—H23A	109.5
N4—C9—N3	114.3 (5)	C22—C23—H23B	109.5
N4—C9—H9	122.9	H23A—C23—H23B	109.5
N3—C9—H9	122.9	C22—C23—H23C	109.5
C12—C11—N4	129.0 (5)	H23A—C23—H23C	109.5
C12—C11—C16	120.5 (5)	H23B—C23—H23C	109.5
N4—C11—C16	110.5 (4)	C22—C24—H24A	109.5
C13—C12—C11	116.8 (5)	C22—C24—H24B	109.5
C13—C12—H12	121.6	H24A—C24—H24B	109.5
C11—C12—H12	121.6	C22—C24—H24C	109.5
C12—C13—C14	122.2 (5)	H24A—C24—H24C	109.5
C12—C13—H13	118.9	H24B—C24—H24C	109.5
C14—C13—H13	118.9	C22'—C24'—H24D	109.5
C13—C14—C15	121.5 (6)	C22'—C24'—H24E	109.5
C13—C14—H14	119.3	H24D—C24'—H24E	109.5
C15—C14—H14	119.3	C22'—C24'—H24F	109.5
C16—C15—C14	116.3 (5)	H24D—C24'—H24F	109.5
C16—C15—H15	121.9	H24E—C24'—H24F	109.5
C14—C15—H15	121.9
C2—N1—C1—N2	−0.1 (5)	C11—C12—C13—C14	−2.2 (9)
C17—N1—C1—N2	−175.5 (4)	C12—C13—C14—C15	2.3 (11)
C7—N2—C1—N1	0.0 (5)	C13—C14—C15—C16	−1.0 (10)
C8—N2—C1—N1	−179.2 (4)	C14—C15—C16—N3	178.3 (6)
C1—N1—C2—C3	178.5 (5)	C14—C15—C16—C11	−0.2 (9)
C17—N1—C2—C3	−6.1 (7)	C9—N3—C16—C15	−179.9 (6)
C1—N1—C2—C7	0.2 (5)	C8—N3—C16—C15	6.3 (9)
C17—N1—C2—C7	175.6 (4)	C9—N3—C16—C11	−1.1 (5)
N1—C2—C3—C4	−176.9 (4)	C8—N3—C16—C11	−174.9 (5)
C7—C2—C3—C4	1.1 (6)	C12—C11—C16—C15	0.2 (8)
C2—C3—C4—C5	−0.5 (7)	N4—C11—C16—C15	179.3 (5)
C3—C4—C5—C6	0.5 (7)	C12—C11—C16—N3	−178.7 (4)
C4—C5—C6—C7	−1.1 (7)	N4—C11—C16—N3	0.4 (5)
C5—C6—C7—N2	177.7 (5)	C1—N1—C17—C18	90.7 (5)
C5—C6—C7—C2	1.7 (7)	C2—N1—C17—C18	−83.9 (5)
C1—N2—C7—C6	−176.3 (5)	C22'—N5—C18—C17	−71.1 (11)
C8—N2—C7—C6	2.9 (8)	C19—N5—C18—C17	133.1 (4)
C1—N2—C7—C2	0.1 (5)	C22—N5—C18—C17	−103.2 (5)
C8—N2—C7—C2	179.4 (4)	N1—C17—C18—N5	−61.6 (5)
C3—C2—C7—C6	−1.8 (7)	C18—N5—C19—C20	−71.9 (5)
N1—C2—C7—C6	176.7 (4)	C22'—N5—C19—C20	131.3 (10)
C3—C2—C7—N2	−178.7 (4)	C22—N5—C19—C20	164.0 (4)
N1—C2—C7—N2	−0.2 (5)	C18—N5—C19—C21	54.3 (5)
C9—N3—C8—N2	−91.4 (7)	C22'—N5—C19—C21	−102.6 (10)
C16—N3—C8—N2	81.2 (7)	C22—N5—C19—C21	−69.8 (5)
C1—N2—C8—N3	−74.6 (7)	C18—N5—C22—C23	51.6 (7)
C7—N2—C8—N3	106.3 (6)	C22'—N5—C22—C23	−68.6 (15)
C11—N4—C9—N3	−1.3 (6)	C19—N5—C22—C23	177.2 (5)
C16—N3—C9—N4	1.6 (7)	C18—N5—C22—C24	169.8 (5)
C8—N3—C9—N4	175.3 (5)	C22'—N5—C22—C24	49.5 (15)
C9—N4—C11—C12	179.6 (5)	C19—N5—C22—C24	−64.6 (6)
C9—N4—C11—C16	0.5 (6)	C18—N5—C22'—C24'	158.1 (13)
N4—C11—C12—C13	−178.0 (5)	C19—N5—C22'—C24'	−47.5 (19)
C16—C11—C12—C13	1.0 (7)	C22—N5—C22'—C24'	−127 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1	0.96	2.75	3.493 (7)	135
C6—H6···Br1i	0.96	2.75	3.702 (6)	173
C20—H20A···Cg1	0.96	2.95	3.445 (5)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Br1	0.96	2.75	3.493 (7)	135
C6—H6⋯Br1i	0.96	2.75	3.702 (6)	173
C20—H20A⋯Cg1	0.96	2.95	3.445 (5)	113

Symmetry code: (i) . Cg1is the centroid of the N1,C1,N2,C7,C2 ring.