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

Wei, T.-B.; Lu, Y.-Y.; Cao, C.; Yao, H.; Zhang, Y.-M.

doi:10.1107/S1600536811023464

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1833

doi:10.1107/S1600536811023464

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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 and You-Ming Zhang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Key Laboratory of Eco-Environment-Related Polymer Materials of the Ministry of Education, Gansu Key Laboratory of Polymer Materials, Northwest Normal University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: zhangnwnu@126.com

(Received 3 May 2011; accepted 16 June 2011; online 30 June 2011)

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 ).

Experimental

Crystal data

C₂₆H₂₃BrN₆
M_r = 499.41
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.086
S = 1.01
5012 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811023464/fy2012sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811023464/fy2012Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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%).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008b).

Figures top

Fig. 1. 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.

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

Crystal data top

C₂₆H₂₃BrN₆	Z = 2
M_r = 499.41	F(000) = 512
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.040P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
5012 reflections	Δρ_max = 0.41 e Å⁻³
299 parameters	Δρ_min = −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)

Crystal data top

C₂₆H₂₃BrN₆	γ = 84.805 (4)°
M_r = 499.41	V = 1372.9 (10) Å³
Triclinic, P1	Z = 2
a = 9.297 (4) Å	Mo Kα radiation
b = 11.869 (5) Å	µ = 1.52 mm⁻¹
c = 13.661 (6) Å	T = 293 K
α = 68.956 (4)°	0.32 × 0.30 × 0.29 mm
β = 77.398 (4)°

Data collection top

Bruker APEXII CCD diffractometer	5012 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	3417 reflections with I > 2σ(I)
T_min = 0.642, T_max = 0.667	R_int = 0.025
9233 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.01	Δρ_max = 0.41 e Å⁻³
5012 reflections	Δρ_min = −0.20 e Å⁻³
299 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	0.02589 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₃BrN₆
M_r	499.41
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.297 (4), 11.869 (5), 13.661 (6)
α, β, γ (°)	68.956 (4), 77.398 (4), 84.805 (4)
V (Å³)	1372.9 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.52
Crystal size (mm)	0.32 × 0.30 × 0.29

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.642, 0.667
No. of measured, independent and observed [I > 2σ(I)] reflections	9233, 5012, 3417
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.086, 1.01
No. of reflections	5012
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.20

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), SHELXTL (Sheldrick, 2008b).

Acknowledgements

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

References

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