1-[2,2-Bis(1,3-benzimidazol-1-ylmeth-yl)-3-bromo-prop-yl]-1,3-benzimidazole.

The title compound, C(26)H(23)BrN(6), has been synthesized as a potential ligand for the construction of metal-organic frameworks. The three benzimidazolyl groups present three potential coordination nodes. The dihedral angles between the benzimidazole ring systems are 74.03 (10), 66.49 (9) and 74.09 (9)°. The structure contains large voids, which contain highly disordered solvent mol-ecules that may be CH(3)CH(2)OH. Since the solvent mol-ecules could not be located, the PLATON/SQUEEZE procedure [Spek (2009 ▶). Acta Cryst. D65, 148-155] was used.

Related literature

For applications of metal organic frameworks, see: Ferey et al. (2005 ▶); Bradshaw et al. (2005 ▶); Pan et al. (2004 ▶); Ko et al. (2002 ▶); Pan et al. (2006 ▶); Barnett & Champness (2003 ▶); Yang et al. (2003 ▶); Liu et al. (2010 ▶). For a related structure, see: Clegg & Martin (2007 ▶).

Experimental

Crystal data

C26H23BrN6

M = 499.41

Triclinic,

a = 9.297 (4) Å

b = 11.869 (5) Å

c = 13.661 (6) Å

α = 68.956 (4)°

β = 77.398 (4)°

γ = 84.805 (4)°

V = 1372.9 (10) Å3

Z = 2

Mo Kα radiation

μ = 1.52 mm−1

T = 293 K

0.32 × 0.30 × 0.29 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.642, T max = 0.667

9233 measured reflections

5012 independent reflections

3417 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.086

S = 1.01

5012 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: SHELXTL (Sheldrick, 2008b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023464/fy2012sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023464/fy2012Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023464/fy2012Isup3.cml

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

C26H23BrN6	Z = 2
Mr = 499.41	F(000) = 512
Triclinic, P1	Dx = 1.208 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.297 (4) Å	Cell parameters from 2851 reflections
b = 11.869 (5) Å	θ = 2.2–22.5°
c = 13.661 (6) Å	µ = 1.52 mm−1
α = 68.956 (4)°	T = 293 K
β = 77.398 (4)°	Block, colourless
γ = 84.805 (4)°	0.32 × 0.30 × 0.29 mm
V = 1372.9 (10) Å3

Bruker APEXII CCD diffractometer	5012 independent reflections
Radiation source: fine-focus sealed tube	3417 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −10→11
Tmin = 0.642, Tmax = 0.667	k = −14→14
9233 measured reflections	l = −12→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
5012 reflections	Δρmax = 0.41 e Å−3
299 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0027 (7)

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
Br1	0.02589 (3)	0.37659 (2)	0.17904 (2)	0.05951 (14)
C18	0.1102 (3)	0.7601 (2)	0.0752 (2)	0.0474 (7)
H18A	0.1910	0.8026	0.0803	0.057*
H18B	0.1263	0.7613	0.0023	0.057*
C9	0.1151 (3)	0.6271 (2)	0.15110 (19)	0.0398 (6)
C26	0.0088 (3)	0.5573 (2)	0.1246 (2)	0.0475 (7)
H26A	0.0211	0.5846	0.0473	0.057*
H26B	−0.0907	0.5791	0.1523	0.057*
C10	0.0700 (3)	0.6261 (2)	0.26770 (19)	0.0463 (6)
H10A	0.1418	0.6722	0.2791	0.056*
H10B	−0.0242	0.6680	0.2748	0.056*
C8	0.2758 (3)	0.5812 (2)	0.13182 (18)	0.0430 (6)
H8A	0.3360	0.6227	0.1576	0.052*
H8B	0.2794	0.4958	0.1735	0.052*
C2	0.5675 (3)	0.7424 (3)	−0.2327 (2)	0.0725 (10)
H2	0.5874	0.7320	−0.2987	0.087*
C5	0.5050 (3)	0.7772 (3)	−0.0330 (2)	0.0596 (8)
H5	0.4843	0.7890	0.0324	0.072*
C1	0.4692 (3)	0.6679 (3)	−0.1461 (2)	0.0540 (7)
C6	0.4383 (3)	0.6874 (2)	−0.0490 (2)	0.0449 (6)
N2	0.3398 (2)	0.59903 (18)	0.01862 (16)	0.0443 (5)
C3	0.6335 (4)	0.8309 (4)	−0.2175 (3)	0.0846 (11)
H3	0.7004	0.8812	−0.2739	0.101*
N1	0.3930 (3)	0.5689 (2)	−0.1371 (2)	0.0638 (7)
C7	0.3198 (3)	0.5320 (3)	−0.0377 (2)	0.0541 (7)
H7	0.2592	0.4650	−0.0088	0.065*
N5	−0.0269 (2)	0.82613 (18)	0.09621 (16)	0.0451 (5)
C21	−0.0100 (4)	1.0452 (3)	0.2290 (3)	0.0700 (9)
H21	0.0508	1.0786	0.2568	0.084*
C19	−0.0459 (3)	0.9106 (2)	0.14554 (19)	0.0411 (6)
C24	−0.1927 (3)	0.9483 (2)	0.1476 (2)	0.0473 (7)
C20	0.0481 (3)	0.9582 (2)	0.1851 (2)	0.0574 (8)
H20	0.1461	0.9332	0.1826	0.069*
C22	−0.1552 (4)	1.0840 (2)	0.2327 (2)	0.0658 (8)
H22	−0.1899	1.1435	0.2618	0.079*
C25	−0.1577 (3)	0.8192 (2)	0.0705 (2)	0.0570 (7)
H25	−0.1722	0.7694	0.0343	0.068*
N6	−0.2618 (3)	0.8885 (2)	0.1011 (2)	0.0629 (7)
C23	−0.2491 (3)	1.0351 (2)	0.1936 (2)	0.0609 (8)
H23	−0.3476	1.0594	0.1977	0.073*
N3	0.0574 (2)	0.50904 (18)	0.35181 (15)	0.0449 (5)
C15	0.1751 (4)	0.2541 (3)	0.5510 (2)	0.0690 (9)
H15	0.1316	0.1831	0.6008	0.083*
C11	0.1656 (3)	0.4432 (2)	0.40562 (19)	0.0449 (6)
C14	0.3172 (4)	0.2784 (3)	0.5444 (3)	0.0776 (10)
H14	0.3712	0.2230	0.5908	0.093*
N4	−0.0525 (3)	0.3426 (2)	0.47523 (18)	0.0602 (6)
C17	−0.0684 (3)	0.4455 (3)	0.3981 (2)	0.0558 (7)
H17	−0.1580	0.4720	0.3774	0.067*
C16	0.0956 (3)	0.3389 (2)	0.4807 (2)	0.0524 (7)
C13	0.3842 (4)	0.3829 (3)	0.4708 (3)	0.0735 (9)
H13	0.4817	0.3964	0.4695	0.088*
C12	0.3103 (3)	0.4681 (3)	0.3990 (2)	0.0558 (7)
H12	0.3556	0.5381	0.3490	0.067*
C4	0.6031 (3)	0.8479 (3)	−0.1189 (3)	0.0792 (10)
H4	0.6508	0.9090	−0.1113	0.095*

	U11	U22	U33	U12	U13	U23
Br1	0.0688 (2)	0.05000 (18)	0.0600 (2)	−0.00572 (13)	−0.00812 (15)	−0.02107 (14)
C18	0.0433 (16)	0.0465 (14)	0.0429 (15)	0.0003 (12)	0.0019 (12)	−0.0106 (12)
C9	0.0348 (14)	0.0419 (13)	0.0385 (14)	−0.0003 (11)	0.0007 (11)	−0.0138 (12)
C26	0.0453 (15)	0.0486 (15)	0.0469 (16)	0.0027 (12)	−0.0081 (13)	−0.0160 (13)
C10	0.0509 (16)	0.0438 (14)	0.0379 (15)	0.0012 (12)	−0.0021 (12)	−0.0110 (12)
C8	0.0403 (15)	0.0491 (14)	0.0373 (15)	0.0027 (12)	−0.0040 (12)	−0.0151 (12)
C2	0.0505 (19)	0.103 (3)	0.0463 (19)	0.0172 (19)	−0.0022 (16)	−0.0139 (19)
C5	0.0447 (17)	0.076 (2)	0.0490 (18)	−0.0088 (15)	−0.0048 (14)	−0.0120 (16)
C1	0.0388 (16)	0.0732 (19)	0.0470 (18)	0.0132 (14)	−0.0046 (13)	−0.0229 (16)
C6	0.0312 (14)	0.0562 (16)	0.0407 (16)	0.0026 (12)	−0.0033 (12)	−0.0120 (13)
N2	0.0353 (12)	0.0538 (13)	0.0438 (13)	0.0039 (10)	−0.0035 (10)	−0.0208 (11)
C3	0.047 (2)	0.111 (3)	0.064 (2)	−0.0079 (19)	0.0009 (17)	0.002 (2)
N1	0.0553 (15)	0.0879 (19)	0.0571 (16)	0.0131 (14)	−0.0085 (13)	−0.0406 (15)
C7	0.0444 (17)	0.0694 (18)	0.0553 (19)	0.0089 (14)	−0.0068 (15)	−0.0341 (16)
N5	0.0389 (13)	0.0449 (12)	0.0477 (13)	0.0017 (10)	−0.0091 (10)	−0.0117 (11)
C21	0.077 (2)	0.0537 (18)	0.087 (2)	−0.0039 (17)	−0.0230 (19)	−0.0290 (18)
C19	0.0403 (15)	0.0350 (13)	0.0406 (15)	−0.0025 (11)	−0.0032 (12)	−0.0068 (12)
C24	0.0426 (16)	0.0414 (14)	0.0509 (16)	0.0054 (12)	−0.0074 (13)	−0.0101 (13)
C20	0.0459 (17)	0.0478 (16)	0.074 (2)	−0.0052 (13)	−0.0127 (15)	−0.0149 (15)
C22	0.079 (2)	0.0481 (17)	0.069 (2)	0.0018 (16)	−0.0088 (18)	−0.0223 (16)
C25	0.0565 (19)	0.0576 (17)	0.0657 (19)	0.0096 (15)	−0.0276 (16)	−0.0254 (15)
N6	0.0518 (15)	0.0614 (15)	0.0823 (18)	0.0124 (12)	−0.0266 (13)	−0.0287 (14)
C23	0.0544 (18)	0.0502 (16)	0.0648 (19)	0.0089 (14)	−0.0052 (15)	−0.0104 (15)
N3	0.0456 (13)	0.0468 (12)	0.0356 (12)	−0.0061 (10)	0.0002 (10)	−0.0100 (10)
C15	0.098 (3)	0.0493 (17)	0.0428 (18)	0.0025 (18)	−0.0012 (18)	−0.0049 (14)
C11	0.0558 (18)	0.0424 (14)	0.0349 (15)	−0.0002 (13)	−0.0059 (13)	−0.0135 (12)
C14	0.087 (3)	0.076 (2)	0.059 (2)	0.016 (2)	−0.018 (2)	−0.0117 (19)
N4	0.0685 (18)	0.0572 (15)	0.0433 (14)	−0.0157 (12)	0.0054 (12)	−0.0100 (12)
C17	0.0486 (17)	0.0661 (19)	0.0484 (17)	−0.0073 (14)	0.0019 (14)	−0.0198 (16)
C16	0.063 (2)	0.0474 (16)	0.0401 (16)	−0.0034 (14)	0.0019 (14)	−0.0144 (14)
C13	0.070 (2)	0.092 (2)	0.063 (2)	0.0081 (19)	−0.0207 (18)	−0.030 (2)
C12	0.0565 (19)	0.0617 (17)	0.0452 (17)	0.0004 (14)	−0.0085 (14)	−0.0150 (14)
C4	0.052 (2)	0.090 (2)	0.079 (3)	−0.0160 (17)	−0.0116 (18)	−0.008 (2)

Br1—C26	2.005 (3)	N5—C19	1.375 (3)
C18—N5	1.463 (3)	C21—C22	1.383 (4)
C18—C9	1.550 (3)	C21—C20	1.384 (4)
C18—H18A	0.9700	C21—H21	0.9300
C18—H18B	0.9700	C19—C20	1.375 (4)
C9—C26	1.522 (3)	C19—C24	1.395 (3)
C9—C8	1.543 (3)	C24—N6	1.381 (3)
C9—C10	1.552 (3)	C24—C23	1.398 (4)
C26—H26A	0.9700	C20—H20	0.9300
C26—H26B	0.9700	C22—C23	1.379 (4)
C10—N3	1.445 (3)	C22—H22	0.9300
C10—H10A	0.9700	C25—N6	1.310 (3)
C10—H10B	0.9700	C25—H25	0.9300
C8—N2	1.475 (3)	C23—H23	0.9300
C8—H8A	0.9700	N3—C17	1.354 (3)
C8—H8B	0.9700	N3—C11	1.389 (3)
C2—C3	1.362 (5)	C15—C14	1.354 (4)
C2—C1	1.393 (4)	C15—C16	1.401 (4)
C2—H2	0.9300	C15—H15	0.9300
C5—C4	1.370 (4)	C11—C12	1.380 (4)
C5—C6	1.383 (4)	C11—C16	1.397 (3)
C5—H5	0.9300	C14—C13	1.382 (4)
C1—N1	1.381 (4)	C14—H14	0.9300
C1—C6	1.393 (4)	N4—C17	1.316 (3)
C6—N2	1.379 (3)	N4—C16	1.391 (4)
N2—C7	1.337 (3)	C17—H17	0.9300
C3—C4	1.397 (5)	C13—C12	1.383 (4)
C3—H3	0.9300	C13—H13	0.9300
N1—C7	1.313 (3)	C12—H12	0.9300
C7—H7	0.9300	C4—H4	0.9300
N5—C25	1.354 (3)
N5—C18—C9	115.32 (19)	C25—N5—C18	128.1 (2)
N5—C18—H18A	108.4	C19—N5—C18	125.5 (2)
C9—C18—H18A	108.4	C22—C21—C20	122.2 (3)
N5—C18—H18B	108.4	C22—C21—H21	118.9
C9—C18—H18B	108.4	C20—C21—H21	118.9
H18A—C18—H18B	107.5	C20—C19—N5	132.8 (2)
C26—C9—C8	112.7 (2)	C20—C19—C24	122.2 (2)
C26—C9—C18	107.1 (2)	N5—C19—C24	105.0 (2)
C8—C9—C18	107.56 (18)	N6—C24—C19	110.6 (2)
C26—C9—C10	112.5 (2)	N6—C24—C23	129.6 (3)
C8—C9—C10	109.21 (19)	C19—C24—C23	119.8 (3)
C18—C9—C10	107.49 (19)	C19—C20—C21	116.9 (3)
C9—C26—Br1	117.62 (17)	C19—C20—H20	121.5
C9—C26—H26A	107.9	C21—C20—H20	121.5
Br1—C26—H26A	107.9	C23—C22—C21	120.5 (3)
C9—C26—H26B	107.9	C23—C22—H22	119.7
Br1—C26—H26B	107.9	C21—C22—H22	119.7
H26A—C26—H26B	107.2	N6—C25—N5	114.2 (3)
N3—C10—C9	116.5 (2)	N6—C25—H25	122.9
N3—C10—H10A	108.2	N5—C25—H25	122.9
C9—C10—H10A	108.2	C25—N6—C24	103.8 (2)
N3—C10—H10B	108.2	C22—C23—C24	118.4 (3)
C9—C10—H10B	108.2	C22—C23—H23	120.8
H10A—C10—H10B	107.3	C24—C23—H23	120.8
N2—C8—C9	113.94 (19)	C17—N3—C11	106.5 (2)
N2—C8—H8A	108.8	C17—N3—C10	125.3 (2)
C9—C8—H8A	108.8	C11—N3—C10	128.1 (2)
N2—C8—H8B	108.8	C14—C15—C16	118.0 (3)
C9—C8—H8B	108.8	C14—C15—H15	121.0
H8A—C8—H8B	107.7	C16—C15—H15	121.0
C3—C2—C1	117.7 (3)	C12—C11—N3	132.1 (2)
C3—C2—H2	121.1	C12—C11—C16	122.6 (2)
C1—C2—H2	121.1	N3—C11—C16	105.1 (2)
C4—C5—C6	116.3 (3)	C15—C14—C13	121.9 (3)
C4—C5—H5	121.8	C15—C14—H14	119.0
C6—C5—H5	121.8	C13—C14—H14	119.0
N1—C1—C6	109.9 (2)	C17—N4—C16	104.3 (2)
N1—C1—C2	130.2 (3)	N4—C17—N3	113.9 (3)
C6—C1—C2	120.0 (3)	N4—C17—H17	123.0
N2—C6—C5	132.1 (3)	N3—C17—H17	123.0
N2—C6—C1	105.3 (2)	N4—C16—C11	110.1 (2)
C5—C6—C1	122.5 (3)	N4—C16—C15	130.4 (3)
C7—N2—C6	106.4 (2)	C11—C16—C15	119.3 (3)
C7—N2—C8	127.9 (2)	C14—C13—C12	121.8 (3)
C6—N2—C8	125.7 (2)	C14—C13—H13	119.1
C2—C3—C4	121.5 (3)	C12—C13—H13	119.1
C2—C3—H3	119.3	C11—C12—C13	116.2 (3)
C4—C3—H3	119.3	C11—C12—H12	121.9
C7—N1—C1	104.1 (2)	C13—C12—H12	121.9
N1—C7—N2	114.3 (3)	C5—C4—C3	121.9 (3)
N1—C7—H7	122.9	C5—C4—H4	119.0
N2—C7—H7	122.9	C3—C4—H4	119.0
C25—N5—C19	106.4 (2)
N5—C18—C9—C26	69.8 (3)	N5—C19—C24—N6	0.1 (3)
N5—C18—C9—C8	−168.8 (2)	C20—C19—C24—C23	−1.6 (4)
N5—C18—C9—C10	−51.3 (3)	N5—C19—C24—C23	179.8 (2)
C8—C9—C26—Br1	46.0 (3)	N5—C19—C20—C21	178.9 (3)
C18—C9—C26—Br1	164.16 (16)	C24—C19—C20—C21	0.8 (4)
C10—C9—C26—Br1	−77.9 (2)	C22—C21—C20—C19	−0.4 (4)
C26—C9—C10—N3	58.1 (3)	C20—C21—C22—C23	1.0 (5)
C8—C9—C10—N3	−67.7 (3)	C19—N5—C25—N6	−1.9 (3)
C18—C9—C10—N3	175.8 (2)	C18—N5—C25—N6	179.1 (2)
C26—C9—C8—N2	64.9 (3)	N5—C25—N6—C24	1.9 (3)
C18—C9—C8—N2	−53.0 (3)	C19—C24—N6—C25	−1.2 (3)
C10—C9—C8—N2	−169.4 (2)	C23—C24—N6—C25	179.2 (3)
C3—C2—C1—N1	−176.6 (3)	C21—C22—C23—C24	−1.8 (4)
C3—C2—C1—C6	1.8 (4)	N6—C24—C23—C22	−178.3 (3)
C4—C5—C6—N2	177.7 (3)	C19—C24—C23—C22	2.1 (4)
C4—C5—C6—C1	0.7 (4)	C9—C10—N3—C17	−93.6 (3)
N1—C1—C6—N2	−0.9 (3)	C9—C10—N3—C11	90.9 (3)
C2—C1—C6—N2	−179.5 (2)	C17—N3—C11—C12	−174.1 (3)
N1—C1—C6—C5	176.8 (2)	C10—N3—C11—C12	2.1 (4)
C2—C1—C6—C5	−1.8 (4)	C17—N3—C11—C16	2.1 (3)
C5—C6—N2—C7	−176.0 (3)	C10—N3—C11—C16	178.3 (2)
C1—C6—N2—C7	1.4 (3)	C16—C15—C14—C13	−0.3 (5)
C5—C6—N2—C8	1.7 (4)	C16—N4—C17—N3	0.6 (3)
C1—C6—N2—C8	179.1 (2)	C11—N3—C17—N4	−1.7 (3)
C9—C8—N2—C7	−79.6 (3)	C10—N3—C17—N4	−178.1 (2)
C9—C8—N2—C6	103.2 (3)	C17—N4—C16—C11	0.8 (3)
C1—C2—C3—C4	−0.7 (5)	C17—N4—C16—C15	176.5 (3)
C6—C1—N1—C7	0.1 (3)	C12—C11—C16—N4	174.8 (2)
C2—C1—N1—C7	178.5 (3)	N3—C11—C16—N4	−1.8 (3)
C1—N1—C7—N2	0.9 (3)	C12—C11—C16—C15	−1.5 (4)
C6—N2—C7—N1	−1.5 (3)	N3—C11—C16—C15	−178.1 (2)
C8—N2—C7—N1	−179.1 (2)	C14—C15—C16—N4	−174.1 (3)
C9—C18—N5—C25	−77.3 (3)	C14—C15—C16—C11	1.3 (4)
C9—C18—N5—C19	103.9 (3)	C15—C14—C13—C12	−0.7 (5)
C25—N5—C19—C20	−177.4 (3)	N3—C11—C12—C13	176.1 (3)
C18—N5—C19—C20	1.6 (4)	C16—C11—C12—C13	0.5 (4)
C25—N5—C19—C24	1.0 (3)	C14—C13—C12—C11	0.6 (5)
C18—N5—C19—C24	180.0 (2)	C6—C5—C4—C3	0.4 (4)
C20—C19—C24—N6	178.7 (2)	C2—C3—C4—C5	−0.4 (5)