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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jun 30;67(Pt 7):o1833. doi: 10.1107/S1600536811023464

1-[2,2-Bis(1,3-benzimidazol-1-ylmeth­yl)-3-bromo­prop­yl]-1,3-benzimidazole

Tai-Bao Wei a, Yan-Yun Lu a, Cheng Cao a, Hong Yao a, You-Ming Zhang a,*
PMCID: PMC3151820  PMID: 21837200

Abstract

The title compound, C26H23BrN6, 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 mol­ecules that may be CH3CH2OH. Since the solvent mol­ecules 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 ▶).graphic file with name e-67-o1833-scheme1.jpg

Experimental

Crystal data

  • C26H23BrN6

  • M r = 499.41

  • Triclinic, Inline graphic

  • 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.

Supplementary Material

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

e-67-o1833-sup1.cif (24.1KB, cif)

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

e-67-o1833-Isup2.hkl (245.5KB, hkl)

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

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

Acknowledgments

This work was supported by the NSFC (No. 21064006) and the Natural Science Foundation of Gansu (1010RJZA018), which are gratefully acknowledged.

supplementary crystallographic information

Comment

In recent years, metal-organic frameworks (MOFs) with network structures have received remarkable attention as a unique class of multifunctional hybrid materials with potential applications in such fields as sorption, molecular separation, luminescence, catalysis, and magnetism (Ferey et al., 2005; Bradshaw et al., 2005; Pan et al., 2004; Ko et al., 2002; Pan et al., 2006). Several N-donor bridging ligands have been investigated for the construction of novel MOFs, for example 1,3-bis(4'-pyridyl)propane, 1,4-bis(4-pyridyl)butane (Barnett et al., 2003), bis(2-benzimidazolylmethyl)(2-pyridylmethyl)amine and bis(2-pyridylmethyl)(2-benzimidazolylmethyl)amine (Yang et al., 2003), 1,1' -(1,4-butanediyl)-bis[2-(2-pyridyl)benzimidazole], 1,1'-(1,6-hexanediyl)bis[2-(2-pyridyl)benzimidazole] and 1,1'-(1,1'-decanediyl)bis-[2-(2-pyridyl)benzimidazole] (Liu et al., 2010).

We designed and synthesized the title compound to be applied as a tridentate ligand. The molecular structure is show in Fig. 1. This ligand is expected to be a good candidate for the construction of coordination polymers with diverse structures. First, the three benzimidazole N atoms of the ligand can act as three potential coordination nodes. Second, the three benzimidazole groups can freely twist around the quaternary carbon atom and the two –CH2– groups to match the requirements of various coordination geometries.

Experimental

To a solution of 1H-benzimidazole (30 mmol) in 100 ml of dry THF/DMSO (10:1 v/v) under nitrogen was added sodium hydroxide (30 mmol) with vigorous stirring at 60 °C. After 1/2 h a solution of tetrakis(bromomethyl)methane(10 mmol) in 20 ml of THF was added over a period of 1 h. The reaction mixture was stirred continuously overnight at 80 °C. A 100 ml portion of water was added to give a precipitant that was recrystallized in EtOH. Then colorless crystals suitable for X-ray diffraction analysis were grown by recrystallization from a 9:1 ethanol:water mixture (yield: 86%).

Refinement

H atoms were included in calclulated positions and refined in a riding-model approximation with C—H distances ranging from 0.93Å to 0.97Å and Uiso(H) = 1.2 Ueq(C). The structure contains large voids, but the disordered solvent molecules could not be located from difference Fourier maps. The PLATON/SQUEEZE procedure (Spek, 2009) was used to account for the electron density in this region.

Figures

Fig. 1.

Fig. 1.

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The structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.

Crystal data

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
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Data collection

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
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Refinement

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)
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Special details

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

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*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, °)

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)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2012).

References

  1. Barnett, S. A. & Champness, N. R. (2003). Coord. Chem. Rev. 246, 145–168.
  2. Bradshaw, D., Claridge, J. B., Cussen, E. J., Prior, T. J. & Rosseinsky, M. J. (2005). Acc. Chem. Res. 38, 273–282. [DOI] [PubMed]
  3. Bruker (2008). SAINT and APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  4. Clegg, W. & Martin, N. C. (2007). Acta Cryst E63, m856.
  5. Ferey, G., Mellot-Draznieks, C., Serre, C. & Millange, F. (2005). Acc. Chem. Res. 38, 217–225. [DOI] [PubMed]
  6. Ko, J. W., Min, K. S. & Suh, M. P. (2002). Inorg. Chem. 41, 2151–2157. [DOI] [PubMed]
  7. Liu, H. Y., Wu, H., Ma, J. F., Liu, Y. Y., Liu, B. & Yang, J. (2010). Cryst. Growth Des. 10, 4795–4805.
  8. Pan, L., Olson, D. H., Ciemnolonski, L. R., Heddy, R. & Li, J. (2006). Angew. Chem. Int. Ed. 45, 616–619. [DOI] [PubMed]
  9. Pan, L., Sander, M. B., Huang, X., Li, J., Smith, M. R. Jr, Bittner, E. W., Bockrath, B. C. & Johnson, J. K. (2004). J. Am. Chem. Soc. 126, 1308–1309. [DOI] [PubMed]
  10. Sheldrick, G. M. (2008a). SADABS University of Göttingen, Germany.
  11. Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  12. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
  13. Yang, X. P., Kang, B. S., Wong, W. K., Su, C. Y. & Liu, H. Q. (2003). Inorg. Chem. 42, 169–179. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-67-o1833-sup1.cif (24.1KB, cif)

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

e-67-o1833-Isup2.hkl (245.5KB, hkl)

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

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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