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ISSN: 2056-9890

2-[(1H-Benzimidazol-2-yl)imino­meth­yl]-4,6-di­bromo­phenol ethanol hemisolvate

aKey Laboratory of Nonferrous Metal Materials and Processing Technology, Department of Material and Chemical Engineering, Guilin University of Technology, Ministry of Education, Guilin 541004, People's Republic of China
*Correspondence e-mail: lisa4.6@163.com

(Received 23 October 2012; accepted 21 January 2013; online 9 February 2013)

The title compound, C14H9Br2N3O·0.5C2H5OH, crystallizes with two 2-[(1H-benzimidazol-2-yl)imino­meth­yl]-4,6-dibromo­phenol mol­ecules and one ethanol solvent mol­ecule in the asymmetric unit. The benzene and benzimidazole rings subtend dihedral angles of 4.5 (3) and 5.2 (2)° in the two mol­ecules. In the crystal, one mol­ecule presents ππ stacking with the equivalent mol­ecule related by inversion, at a distance of 3.30 Å (separation between mol­ecular mean planes). A three-dimensional network is formed through N—H⋯N, N—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For background to benzimidazole compounds, see: Zhang et al. (2008[Zhang, S.-H., Zeng, M.-H. & Liang, H. (2008). J. Coord. Chem. 61, 2422-2427.], 2011[Zhang, S.-H., Ma, L.-F., Zou, H.-H., Wang, Y.-G., Liang, H. & Zeng, M.-H. (2011). Dalton Trans. 40, 11402-11409.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9Br2N3O·0.5C2H6O

  • Mr = 836.19

  • Monoclinic, P 21 /c

  • a = 14.5300 (15) Å

  • b = 16.8190 (14) Å

  • c = 13.8491 (17) Å

  • β = 111.656 (13)°

  • V = 3145.5 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 5.16 mm−1

  • T = 293 K

  • 0.23 × 0.22 × 0.21 mm

Data collection
  • Agilent SuperNova Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.436, Tmax = 1.000

  • 19465 measured reflections

  • 6390 independent reflections

  • 4189 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.133

  • S = 1.03

  • 6390 reflections

  • 392 parameters

  • H-atom parameters constrained

  • Δρmax = 1.55 e Å−3

  • Δρmin = −0.76 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N5—H5⋯N3 0.86 2.14 2.997 (4) 172
N2—H2A⋯O3i 0.86 2.00 2.816 (4) 157
O1—H1⋯N1 0.82 1.90 2.618 (6) 146
O2—H2⋯N4 0.82 1.92 2.640 (6) 147
O3—H3⋯N6ii 0.82 2.08 2.900 (5) 176
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Benzimidazole compounds exhibit a large range of biological activities and so far various types of benzimidazole drugs have been extensively used in clinic practice (Zhang et al., 2008, 2011). Herein, we have synthesized a new benzimidazole compound.

In the title compound, the benzene and benzimidazole rings are almost in the same plane, and the dihedral angle between the benzene and benzimidazole rings is 4.5 (3) and 5.2 (2)° for each crystallographically independent molecule (Fig. 1). ππ stacking interactions are observed between the benzene and benzimidazole rings of molecules C1···C14 related by inversion: the dihedral angle between stacked molecules is 0°, and the separation between mean planes formed by the benzene and the benzimidazole rings in the molecules is 3.487 Å (Fig. 2). The title compound forms a three-dimensional network in the crystal structure, through N—H···N, N—H···O and O—H···N hydrgoen bonds (Fig. 3).

Related literature top

For background to benzimidazole compounds, see: Zhang et al. (2008, 2011).

Experimental top

3,5-Dibromosalicylaldehyde (3.0 mmol) was dissolved in a round bottom flask containing ethanol (20 ml). To this solution, an ethanolic solution (10 ml) of 2-aminobenzimidazole (3.0 mmol) was then added dropwise, and the mixture was refluxed for 4 h. After cooling down to room temperature, the resulting orange precipitate was filtered off, and recrystallized from ethanol. Orange block-like crystals of the title compound were obtained by slow evaporation of the filtrate at room temperature.

Refinement top

H atoms on C, N, and O atoms were positioned geometrically and refined using a riding model (C—Haromatic = 0.93 Å, CHethanol = 0.97 Å, N—H = 0.86 Å and O—H = 0.82 Å) with Uiso(H) = 1.2Ueq(carrier atom), except for the methyl group in the ethanol molecule and hydroxyl groups, for which Uiso(H) = 1.5Ueq(carrier atom).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of one independent molecule in the title compound, showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Perspective view of the stacking of two inversion-related molecules in the title compound.
[Figure 3] Fig. 3. Three-dimensional network of the title compound, with dashed lines showing hydrogen bonds.
2-[(1H-Benzimidazol-2-yl)iminomethyl]-4,6-dibromophenol ethanol hemisolvate top
Crystal data top
C14H9Br2N3O·0.5C2H6OF(000) = 1640
Mr = 836.19Dx = 1.766 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6390 reflections
a = 14.5300 (15) Åθ = 2.8–29.1°
b = 16.8190 (14) ŵ = 5.16 mm1
c = 13.8491 (17) ÅT = 293 K
β = 111.656 (13)°Block, orange
V = 3145.5 (6) Å30.23 × 0.22 × 0.21 mm
Z = 4
Data collection top
Agilent SuperNova Eos
diffractometer
6390 independent reflections
Radiation source: fine-focus sealed tube4189 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ω scansθmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
h = 1718
Tmin = 0.436, Tmax = 1.000k = 1221
19465 measured reflectionsl = 1716
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0525P)2 + 1.2028P]
where P = (Fo2 + 2Fc2)/3
6390 reflections(Δ/σ)max = 0.001
392 parametersΔρmax = 1.55 e Å3
0 restraintsΔρmin = 0.76 e Å3
0 constraints
Crystal data top
C14H9Br2N3O·0.5C2H6OV = 3145.5 (6) Å3
Mr = 836.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.5300 (15) ŵ = 5.16 mm1
b = 16.8190 (14) ÅT = 293 K
c = 13.8491 (17) Å0.23 × 0.22 × 0.21 mm
β = 111.656 (13)°
Data collection top
Agilent SuperNova Eos
diffractometer
6390 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
4189 reflections with I > 2σ(I)
Tmin = 0.436, Tmax = 1.000Rint = 0.051
19465 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.03Δρmax = 1.55 e Å3
6390 reflectionsΔρmin = 0.76 e Å3
392 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.18346 (5)0.58511 (4)0.49389 (5)0.0651 (2)
Br20.16183 (5)0.34709 (4)0.19662 (5)0.0773 (2)
Br30.20356 (4)0.66995 (4)0.13312 (5)0.0682 (2)
Br40.02247 (4)0.43016 (4)0.16402 (5)0.0687 (2)
O10.3836 (3)0.6096 (2)0.4833 (3)0.0523 (9)
H10.43780.61700.47930.078*
O20.3869 (3)0.5833 (2)0.1429 (3)0.0509 (9)
H20.43690.55790.14910.076*
O30.5513 (3)0.7478 (2)0.0641 (3)0.0584 (10)
H30.51140.71660.02490.088*
N10.5251 (3)0.5886 (2)0.4114 (3)0.0410 (10)
N20.6683 (3)0.6647 (2)0.4789 (3)0.0391 (9)
H2A0.64730.69080.52010.047*
N30.6673 (3)0.5779 (2)0.3570 (3)0.0383 (9)
N40.4902 (3)0.4627 (2)0.1140 (3)0.0380 (9)
N50.6607 (3)0.4473 (2)0.2074 (3)0.0398 (9)
H50.66540.48770.24700.048*
N60.5910 (3)0.3573 (2)0.0821 (3)0.0365 (9)
C10.2409 (3)0.5300 (3)0.4110 (4)0.0430 (12)
C20.1890 (3)0.4700 (3)0.3465 (4)0.0463 (13)
H2B0.12580.45670.34300.056*
C30.2322 (4)0.4295 (3)0.2863 (4)0.0438 (12)
C40.3270 (3)0.4493 (3)0.2931 (4)0.0448 (12)
H40.35570.42170.25330.054*
C50.3790 (3)0.5090 (3)0.3576 (3)0.0380 (11)
C60.3357 (3)0.5508 (3)0.4174 (4)0.0383 (11)
C70.4786 (3)0.5289 (3)0.3606 (3)0.0395 (11)
H70.50780.49730.32480.047*
C80.6193 (3)0.6076 (3)0.4121 (4)0.0351 (10)
C90.7585 (3)0.6735 (3)0.4691 (4)0.0425 (12)
C100.8406 (4)0.7209 (3)0.5210 (4)0.0565 (14)
H100.84150.75600.57320.068*
C110.9220 (4)0.7126 (4)0.4902 (5)0.0679 (18)
H110.97920.74200.52330.081*
C120.9177 (4)0.6611 (4)0.4110 (5)0.0677 (18)
H120.97210.65800.39120.081*
C130.8372 (4)0.6143 (3)0.3604 (5)0.0574 (15)
H130.83680.58020.30740.069*
C140.7557 (3)0.6193 (3)0.3904 (4)0.0392 (11)
C150.2131 (4)0.5794 (3)0.0568 (4)0.0447 (13)
C160.1299 (4)0.5450 (3)0.0139 (4)0.0472 (13)
H160.06800.56710.02600.057*
C170.1377 (3)0.4775 (3)0.0673 (4)0.0444 (12)
C180.2293 (3)0.4427 (3)0.0496 (4)0.0434 (12)
H180.23390.39700.08550.052*
C190.3148 (3)0.4774 (3)0.0231 (3)0.0367 (11)
C200.3075 (3)0.5466 (3)0.0751 (4)0.0387 (11)
C210.4092 (3)0.4375 (3)0.0437 (4)0.0410 (12)
H210.41110.39260.00530.049*
C220.5779 (3)0.4202 (3)0.1318 (4)0.0351 (11)
C230.6906 (3)0.3406 (3)0.1292 (3)0.0341 (10)
C240.7478 (4)0.2809 (3)0.1087 (4)0.0473 (13)
H240.71890.24320.05730.057*
C250.8469 (4)0.2791 (3)0.1662 (4)0.0517 (14)
H250.88570.23950.15350.062*
C260.8919 (4)0.3357 (3)0.2441 (4)0.0478 (13)
H260.95980.33260.28110.057*
C270.8391 (3)0.3952 (3)0.2674 (4)0.0440 (12)
H270.86900.43250.31910.053*
C280.7368 (3)0.3966 (3)0.2085 (3)0.0357 (11)
C290.5640 (5)0.7298 (4)0.1691 (5)0.0677 (17)
H29A0.62960.74660.21430.081*
H29B0.56020.67260.17620.081*
C300.4904 (6)0.7678 (4)0.2036 (5)0.089 (2)
H30A0.42630.74530.16650.134*
H30B0.48880.82390.19000.134*
H30C0.50810.75920.27670.134*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0689 (4)0.0622 (4)0.0823 (5)0.0184 (3)0.0492 (4)0.0108 (3)
Br20.0635 (4)0.0832 (5)0.0757 (5)0.0212 (3)0.0146 (4)0.0247 (4)
Br30.0597 (4)0.0671 (4)0.0849 (5)0.0064 (3)0.0350 (4)0.0178 (3)
Br40.0352 (3)0.0942 (5)0.0658 (4)0.0026 (3)0.0059 (3)0.0097 (3)
O10.048 (2)0.055 (2)0.058 (2)0.0017 (18)0.025 (2)0.0100 (19)
O20.046 (2)0.055 (2)0.048 (2)0.0020 (17)0.0122 (19)0.0030 (18)
O30.062 (3)0.062 (3)0.047 (2)0.0218 (19)0.016 (2)0.0002 (19)
N10.038 (2)0.043 (3)0.039 (2)0.0001 (18)0.011 (2)0.0035 (19)
N20.039 (2)0.041 (2)0.038 (2)0.0034 (18)0.015 (2)0.0022 (18)
N30.036 (2)0.041 (2)0.040 (2)0.0040 (17)0.016 (2)0.0000 (18)
N40.032 (2)0.050 (3)0.031 (2)0.0020 (18)0.0109 (19)0.0026 (18)
N50.033 (2)0.049 (3)0.038 (2)0.0006 (18)0.0135 (19)0.0110 (19)
N60.028 (2)0.044 (2)0.036 (2)0.0030 (17)0.0102 (18)0.0009 (18)
C10.039 (3)0.052 (3)0.038 (3)0.011 (2)0.014 (2)0.011 (2)
C20.032 (3)0.055 (3)0.051 (3)0.004 (2)0.014 (3)0.017 (3)
C30.037 (3)0.053 (3)0.034 (3)0.002 (2)0.004 (2)0.007 (2)
C40.038 (3)0.062 (4)0.033 (3)0.000 (2)0.012 (2)0.002 (2)
C50.034 (3)0.046 (3)0.032 (3)0.002 (2)0.010 (2)0.008 (2)
C60.039 (3)0.037 (3)0.034 (3)0.005 (2)0.007 (2)0.010 (2)
C70.036 (3)0.052 (3)0.029 (3)0.011 (2)0.011 (2)0.004 (2)
C80.029 (2)0.037 (3)0.035 (3)0.001 (2)0.007 (2)0.003 (2)
C90.032 (3)0.046 (3)0.043 (3)0.003 (2)0.006 (2)0.010 (2)
C100.052 (4)0.051 (4)0.051 (3)0.006 (3)0.001 (3)0.002 (3)
C110.037 (3)0.071 (4)0.081 (5)0.015 (3)0.006 (3)0.023 (4)
C120.033 (3)0.077 (5)0.092 (5)0.002 (3)0.022 (3)0.020 (4)
C130.047 (3)0.060 (4)0.072 (4)0.008 (3)0.031 (3)0.009 (3)
C140.033 (3)0.041 (3)0.041 (3)0.007 (2)0.010 (2)0.008 (2)
C150.047 (3)0.049 (3)0.045 (3)0.010 (2)0.025 (3)0.011 (2)
C160.033 (3)0.062 (4)0.048 (3)0.010 (2)0.017 (3)0.009 (3)
C170.034 (3)0.058 (3)0.038 (3)0.003 (2)0.011 (2)0.008 (2)
C180.039 (3)0.049 (3)0.043 (3)0.002 (2)0.016 (3)0.003 (2)
C190.031 (3)0.043 (3)0.035 (3)0.007 (2)0.011 (2)0.009 (2)
C200.031 (3)0.049 (3)0.033 (3)0.001 (2)0.009 (2)0.008 (2)
C210.040 (3)0.049 (3)0.036 (3)0.003 (2)0.016 (2)0.001 (2)
C220.030 (3)0.042 (3)0.033 (3)0.001 (2)0.011 (2)0.002 (2)
C230.031 (2)0.039 (3)0.030 (3)0.001 (2)0.009 (2)0.002 (2)
C240.051 (3)0.041 (3)0.051 (3)0.004 (2)0.020 (3)0.006 (2)
C250.044 (3)0.051 (3)0.064 (4)0.017 (3)0.025 (3)0.007 (3)
C260.032 (3)0.057 (4)0.052 (3)0.011 (2)0.014 (3)0.011 (3)
C270.032 (3)0.059 (3)0.039 (3)0.000 (2)0.010 (2)0.002 (2)
C280.029 (2)0.047 (3)0.033 (3)0.006 (2)0.013 (2)0.000 (2)
C290.076 (4)0.061 (4)0.057 (4)0.012 (3)0.013 (3)0.008 (3)
C300.122 (6)0.081 (5)0.074 (5)0.020 (4)0.047 (5)0.007 (4)
Geometric parameters (Å, º) top
Br1—C11.893 (5)C9—C141.410 (7)
Br2—C31.891 (5)C10—C111.405 (7)
Br3—C151.889 (5)C10—H100.9300
Br4—C171.891 (5)C11—C121.380 (8)
O1—C61.352 (6)C11—H110.9300
O1—H10.8200C12—C131.369 (8)
O2—C201.340 (5)C12—H120.9300
O2—H20.8200C13—C141.396 (6)
O3—C291.428 (6)C13—H130.9300
O3—H30.8200C15—C161.372 (7)
N1—C71.268 (6)C15—C201.411 (6)
N1—C81.401 (5)C16—C171.382 (7)
N2—C81.342 (6)C16—H160.9300
N2—C91.374 (5)C17—C181.389 (6)
N2—H2A0.8600C18—C191.406 (6)
N3—C81.309 (5)C18—H180.9300
N3—C141.381 (6)C19—C201.394 (7)
N4—C211.291 (6)C19—C211.457 (6)
N4—C221.401 (5)C21—H210.9300
N5—C221.350 (6)C23—C241.397 (6)
N5—C281.392 (5)C23—C281.414 (6)
N5—H50.8600C24—C251.365 (7)
N6—C221.313 (6)C24—H240.9300
N6—C231.380 (5)C25—C261.406 (7)
C1—C21.373 (7)C25—H250.9300
C1—C61.392 (6)C26—C271.372 (7)
C2—C31.391 (7)C26—H260.9300
C2—H2B0.9300C27—C281.407 (6)
C3—C41.386 (6)C27—H270.9300
C4—C51.370 (7)C29—C301.469 (8)
C4—H40.9300C29—H29A0.9700
C5—C61.401 (6)C29—H29B0.9700
C5—C71.470 (6)C30—H30A0.9600
C7—H70.9300C30—H30B0.9600
C9—C101.393 (7)C30—H30C0.9600
C6—O1—H1109.5C16—C15—C20120.4 (5)
C20—O2—H2109.5C16—C15—Br3120.8 (4)
C29—O3—H3109.5C20—C15—Br3118.8 (4)
C7—N1—C8120.3 (4)C15—C16—C17120.2 (4)
C8—N2—C9107.0 (4)C15—C16—H16119.9
C8—N2—H2A126.5C17—C16—H16119.9
C9—N2—H2A126.5C16—C17—C18120.9 (5)
C8—N3—C14104.0 (4)C16—C17—Br4119.9 (4)
C21—N4—C22118.8 (4)C18—C17—Br4119.2 (4)
C22—N5—C28106.2 (4)C17—C18—C19119.2 (5)
C22—N5—H5126.9C17—C18—H18120.4
C28—N5—H5126.9C19—C18—H18120.4
C22—N6—C23104.3 (4)C20—C19—C18120.1 (4)
C2—C1—C6121.3 (4)C20—C19—C21122.0 (4)
C2—C1—Br1119.7 (4)C18—C19—C21117.9 (4)
C6—C1—Br1119.1 (4)O2—C20—C19122.5 (4)
C1—C2—C3119.2 (4)O2—C20—C15118.3 (5)
C1—C2—H2B120.4C19—C20—C15119.2 (4)
C3—C2—H2B120.4N4—C21—C19121.8 (4)
C4—C3—C2119.9 (5)N4—C21—H21119.1
C4—C3—Br2120.2 (4)C19—C21—H21119.1
C2—C3—Br2119.9 (4)N6—C22—N5114.7 (4)
C5—C4—C3121.0 (4)N6—C22—N4128.1 (4)
C5—C4—H4119.5N5—C22—N4117.1 (4)
C3—C4—H4119.5N6—C23—C24130.5 (4)
C4—C5—C6119.5 (4)N6—C23—C28110.2 (4)
C4—C5—C7119.1 (4)C24—C23—C28119.3 (4)
C6—C5—C7121.4 (4)C25—C24—C23118.4 (5)
O1—C6—C1118.5 (4)C25—C24—H24120.8
O1—C6—C5122.4 (4)C23—C24—H24120.8
C1—C6—C5119.1 (5)C24—C25—C26121.6 (5)
N1—C7—C5121.0 (4)C24—C25—H25119.2
N1—C7—H7119.5C26—C25—H25119.2
C5—C7—H7119.5C27—C26—C25122.2 (5)
N3—C8—N2114.4 (4)C27—C26—H26118.9
N3—C8—N1129.7 (4)C25—C26—H26118.9
N2—C8—N1115.9 (4)C26—C27—C28116.0 (5)
N2—C9—C10132.6 (5)C26—C27—H27122.0
N2—C9—C14104.5 (4)C28—C27—H27122.0
C10—C9—C14122.9 (5)N5—C28—C27132.9 (4)
C9—C10—C11116.3 (5)N5—C28—C23104.6 (4)
C9—C10—H10121.9C27—C28—C23122.5 (4)
C11—C10—H10121.9O3—C29—C30113.7 (5)
C12—C11—C10120.5 (5)O3—C29—H29A108.8
C12—C11—H11119.8C30—C29—H29A108.8
C10—C11—H11119.8O3—C29—H29B108.8
C13—C12—C11123.2 (5)C30—C29—H29B108.8
C13—C12—H12118.4H29A—C29—H29B107.7
C11—C12—H12118.4C29—C30—H30A109.5
C12—C13—C14118.1 (6)C29—C30—H30B109.5
C12—C13—H13120.9H30A—C30—H30B109.5
C14—C13—H13120.9C29—C30—H30C109.5
N3—C14—C13131.0 (5)H30A—C30—H30C109.5
N3—C14—C9110.1 (4)H30B—C30—H30C109.5
C13—C14—C9118.9 (5)
C6—C1—C2—C30.1 (7)C20—C15—C16—C170.5 (7)
Br1—C1—C2—C3179.6 (3)Br3—C15—C16—C17178.3 (4)
C1—C2—C3—C40.8 (7)C15—C16—C17—C180.8 (7)
C1—C2—C3—Br2179.8 (4)C15—C16—C17—Br4179.6 (3)
C2—C3—C4—C50.7 (7)C16—C17—C18—C190.5 (7)
Br2—C3—C4—C5179.9 (4)Br4—C17—C18—C19179.3 (3)
C3—C4—C5—C60.2 (7)C17—C18—C19—C201.2 (7)
C3—C4—C5—C7178.8 (4)C17—C18—C19—C21177.1 (4)
C2—C1—C6—O1179.2 (4)C18—C19—C20—O2178.1 (4)
Br1—C1—C6—O10.3 (6)C21—C19—C20—O23.8 (7)
C2—C1—C6—C50.7 (7)C18—C19—C20—C152.5 (7)
Br1—C1—C6—C5178.8 (3)C21—C19—C20—C15175.7 (4)
C4—C5—C6—O1179.2 (4)C16—C15—C20—O2178.3 (4)
C7—C5—C6—O12.2 (7)Br3—C15—C20—O22.8 (6)
C4—C5—C6—C10.9 (7)C16—C15—C20—C192.2 (7)
C7—C5—C6—C1179.4 (4)Br3—C15—C20—C19176.7 (3)
C8—N1—C7—C5178.9 (4)C22—N4—C21—C19178.2 (4)
C4—C5—C7—N1173.0 (5)C20—C19—C21—N42.6 (7)
C6—C5—C7—N15.5 (7)C18—C19—C21—N4175.6 (4)
C14—N3—C8—N20.1 (5)C23—N6—C22—N50.6 (5)
C14—N3—C8—N1179.9 (5)C23—N6—C22—N4178.9 (4)
C9—N2—C8—N31.0 (6)C28—N5—C22—N60.4 (5)
C9—N2—C8—N1179.0 (4)C28—N5—C22—N4178.9 (4)
C7—N1—C8—N38.9 (8)C21—N4—C22—N63.2 (7)
C7—N1—C8—N2171.1 (4)C21—N4—C22—N5178.5 (4)
C8—N2—C9—C10177.0 (5)C22—N6—C23—C24179.3 (5)
C8—N2—C9—C141.6 (5)C22—N6—C23—C280.5 (5)
N2—C9—C10—C11178.9 (5)N6—C23—C24—C25178.3 (5)
C14—C9—C10—C110.5 (7)C28—C23—C24—C250.4 (7)
C9—C10—C11—C121.4 (8)C23—C24—C25—C260.2 (8)
C10—C11—C12—C131.7 (9)C24—C25—C26—C270.5 (8)
C11—C12—C13—C140.1 (9)C25—C26—C27—C280.2 (7)
C8—N3—C14—C13179.8 (5)C22—N5—C28—C27178.2 (5)
C8—N3—C14—C91.2 (5)C22—N5—C28—C230.0 (5)
C12—C13—C14—N3177.1 (5)C26—C27—C28—N5178.5 (5)
C12—C13—C14—C91.8 (7)C26—C27—C28—C230.5 (7)
N2—C9—C14—N31.8 (5)N6—C23—C28—N50.3 (5)
C10—C9—C14—N3177.0 (4)C24—C23—C28—N5179.3 (4)
N2—C9—C14—C13179.1 (4)N6—C23—C28—C27178.1 (4)
C10—C9—C14—C132.1 (7)C24—C23—C28—C270.8 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···N30.862.142.997 (4)172
N2—H2A···O3i0.862.002.816 (4)157
O1—H1···N10.821.902.618 (6)146
O2—H2···N40.821.922.640 (6)147
O3—H3···N6ii0.822.082.900 (5)176
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC14H9Br2N3O·0.5C2H6O
Mr836.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)14.5300 (15), 16.8190 (14), 13.8491 (17)
β (°) 111.656 (13)
V3)3145.5 (6)
Z4
Radiation typeMo Kα
µ (mm1)5.16
Crystal size (mm)0.23 × 0.22 × 0.21
Data collection
DiffractometerAgilent SuperNova Eos
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.436, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
19465, 6390, 4189
Rint0.051
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.133, 1.03
No. of reflections6390
No. of parameters392
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.55, 0.76

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···N30.862.142.997 (4)172
N2—H2A···O3i0.862.002.816 (4)157
O1—H1···N10.821.902.618 (6)146
O2—H2···N40.821.922.640 (6)147
O3—H3···N6ii0.822.082.900 (5)176
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y+1, z.
 

Acknowledgements

The authors acknowledge financial support by the National Natural Science Foundation of China (No. 2126606).

References

First citationAgilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationZhang, S.-H., Ma, L.-F., Zou, H.-H., Wang, Y.-G., Liang, H. & Zeng, M.-H. (2011). Dalton Trans. 40, 11402–11409.  Web of Science CSD CrossRef CAS PubMed
First citationZhang, S.-H., Zeng, M.-H. & Liang, H. (2008). J. Coord. Chem. 61, 2422–2427.  CAS

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