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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 2| February 2012| Pages o466-o467

3,3′-[1,2-Phenyl­enebis(methyl­ene)]bis­­(1-propyl­benzimidazolium) dibromide hemihydrate

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 6 January 2012; accepted 13 January 2012; online 21 January 2012)

The asymmetric unit of the title compound, C28H32N42+·2Br·0.5H2O, contains one 3,3′-[1,2-phenyl­enebis(methyl­ene)]bis­(1-propyl­benzimidazolium) cation, two bromide anions and one half-mol­ecule of water. In the crystal, the whole 3,3′-[1,2-phen­yl­enebis(methyl­ene)]bis­(1-propyl­benzimidazolium) cation and one of the bromide anions are each disordered over two positions with site-occupancy ratios of 0.751 (6):0.249 (6) and 0.680 (8):0.320 (8). For the major component of the disordered cation, the central benzene ring forms dihedral angles of 83.6 (5) and 88.2 (4)° with its adjacent imidazole rings, while these angles for the minor component are 89.2 (15) and 84.9 (13)°. In the crystal, the cations and anions are linked by C—H⋯Br hydrogen bonds into dimers and then stacked along the c axis. The crystal packing is further stabilized by C—H⋯π and ππ inter­actions [shortest centroid–centroid distance = 3.646 (4) Å].

Related literature

For details and applications (biological and catalytic) of N-heterocyclic carbenes, see: Herrmann (2002[Herrmann, W. A. (2002). Angew. Chem. Int. Ed. 41, 1290-1309.]); Winkelmann & Navarro (2010[Winkelmann, O. H. & Navarro, O. (2010). Adv. Synth. Catal. 352, 212-214.]); Kascatan-Nebioglu et al. (2007[Kascatan-Nebioglu, A., Panzner, M. J., Tessier, C. A., Cannon, C. L. & Youngs, W. J. (2007). Coord. Chem. Rev. 251, 884-895.]); Ruan et al. (2009[Ruan, B., Tian, Y., Zhou, H., Wu, J., Liu, Z., Zhu, C., Yang, J. & Zhu, H. (2009). J. Organomet. Chem. 694, 2883-2887.]); Barnard et al. (2004[Barnard, P. J., Baker, M. V., Berners-Price, S. J. & Day, D. A. J. (2004). J. Inorg. Biochem. 98, 1642-1647.]); Teyssot et al. (2009[Teyssot, M.-L., Jarrousse, A.-S., Manin, M., Chevry, A., Roche, S., Norre, F., Beaudoin, C., Morel, L., Boyer, D., Mahiou, R. & Gautier, A. (2009). Dalton Trans. pp. 6894-6902.]); Herrmann et al. (1995[Herrmann, W. A., Elison, M., Fischer, J., Köcher, C. & Artus, G. R. J. (1995). Angew. Chem. Int. Ed. 34, 2371-2374.], 1996[Herrmann, W. A., Goossen, L. J., Köcher, C. & Artus, G. R. J. (1996). Angew. Chem. Int. Ed. 35, 2805-2807.]); Cheng & Trudell (2001[Cheng, J. & Trudell, M. L. (2001). Org. Lett. 3, 1371-1374.]); Lee & Hartwig (2001[Lee, S. & Hartwig, J. F. (2001). J. Org. Chem. 66, 3402-3415.]); Weskamp et al. (1998[Weskamp, T., Schattenmann, W. C., Spiegler, M. & Herrmann, W. A. (1998). Angew. Chem. Int. Ed. 37, 2490-2493.]); Choi et al. (2001[Choi, T.-L., Chatterjee, A. K. & Grubbs, R. H. (2001). Angew. Chem. Int. Ed. 40, 1277-1279.]). For a related structure, see: Haque et al. (2011[Haque, R. A., Iqbal, M. A., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o1814-o1815.]).

[Scheme 1]

Experimental

Crystal data
  • C28H32N42+·2Br·0.5H2O

  • Mr = 593.40

  • Triclinic, [P \overline 1]

  • a = 9.0465 (4) Å

  • b = 11.4348 (5) Å

  • c = 14.4143 (7) Å

  • α = 74.013 (1)°

  • β = 82.935 (1)°

  • γ = 70.817 (1)°

  • V = 1352.96 (11) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.02 mm−1

  • T = 296 K

  • 0.54 × 0.44 × 0.26 mm

Data collection
  • Bruker APEX DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.290, Tmax = 0.505

  • 39695 measured reflections

  • 10937 independent reflections

  • 6959 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.133

  • S = 1.01

  • 10937 reflections

  • 601 parameters

  • 86 restraints

  • H-atom parameters constrained

  • Δρmax = 0.58 e Å−3

  • Δρmin = −0.47 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg6 and Cg8 are the centroids of the N1X/C8X/C13X/N2X/C14X and C1X–C6X rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5A⋯Br1i 0.93 2.87 3.665 (4) 144
C7—H7A⋯Br1ii 0.97 2.75 3.596 (9) 146
C14—H14A⋯Br1ii 0.93 2.87 3.618 (7) 138
C20—H20A⋯Br1ii 0.93 2.87 3.699 (6) 148
C5—H5ACg6 0.93 2.82 3.405 (14) 122
C28—H28ACg8iii 0.96 2.99 3.607 (15) 123
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y, -z+1; (iii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

N-Heterocyclic Carbenes (NHCs) have become universal ligands in organometallic and inorganic coordination chemistry (Herrmann, 2002) as their complexes have widespread biological and catalytic applications (Winkelmann & Navarro, 2010). Metal complexes of NHCs (for example, gold, silver and platinum) have proven to be potential antimicrobial (Kascatan-Nebioglu et al., 2007), antibacterial (Ruan, et al., 2009), antimitochondrial (Barnard et al., 2004) and anticancer (Teyssot et al., 2009) agents. Because of its specific coordination chemistry, this class also exhibits excellent catalytic activity for Heck and Suzuki coupling reactions (Herrmann et al., 1995) as well as aryl amination (Cheng & Trudell, 2001), amide α-arylation (Lee & Hartwig, 2001), hydrosilation (Herrmann et al., 1996), olefin metathesis (Weskamp et al., 1998), and metathesis cross-coupling reactions (Choi et al., 2001).

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit consists of one 3,3'-[1,2-phenylenebis(methylene)]bis(1-propyl-benzimidazolium) cation, two bromide anions and one half-molecule of water. In the crystal, the whole cation is disordered over two sites with occupancy ratio of 0.751 (6):0.249 (6), whereas the site-occupancy ratio for disordered bromide anion is equal to 0.680 (8):0.320 (8). For the major disordered cation, the central benzene ring (C1–C6) forms dihedral angles of 83.6 (5) and 88.2 (4)°, respectively, with its adjacent imidazole (N1/N2/C8/C13/C14) and (N3/N4/C19/C24/C25) rings; whereas for the minor disordered cation, the central benzene ring (C1X–C6X) forms dihedral angles of 89.2 (15) and 84.9 (13)°, respectively, with its adjacent imidazole (N1X/N2X/C8X/C13X/C14X) and (N3X/N4X/C19X/C24X/C25X) rings. Bond lengths and angles are comparable to related structure (Haque et al., 2011).

In the crystal structure, Fig. 2, the molecules are interconnected by C5—H5A···Br1, C7—H7A···Br1, C14—H14A···Br1 and C20—H20A···Br1 hydrogen bonds (Table 1) into dimers and then stacked along c axis. The crystal structure is further stabilized by C—H···π interactions (Table 1). ππ Interactions were also observed with Cg2···Cg5 distance = 3.750 (4) Å (symmetry code: 1-x, -y, 1-z), Cg4···Cg4 distance = 3.808 (5) Å (symmetry code: 1-x, 1-y, 2-z) and Cg5···Cg5 distance = 3.646 (4) Å (symmetry code: 1-x, -y, 1-z); Cg2, Cg4 and Cg5 are the centroids of N3/N4/C19/C24/C25, C8–C13 and C19–C24 rings, respectively.

Related literature top

For details and applications (biological and catalytic) of N-heterocyclic carbenes, see: Herrmann (2002); Winkelmann & Navarro (2010); Kascatan-Nebioglu et al. (2007); Ruan et al. (2009); Barnard et al. (2004); Teyssot et al. (2009); Herrmann et al. (1995, 1996); Cheng & Trudell (2001); Lee & Hartwig (2001); Weskamp et al. (1998); Choi et al. (2001). For a related structure, see: Haque et al. (2011).

Experimental top

A mixture of benzimidazole (2.36 g, 20 mmol) and finely ground potassium hydroxide (2.36 g, 30 mmol) in 30 ml of DMSO was stirred at room temperature (27–28 °C) for 30 minutes. 1-Bromopropane (1.82 ml, 20 mmol) was added drop-wise in this consistently stirred mixture with further stirring for 2 h at the same temperature. The mixture was then poured into water (300 ml) and was extracted by chloroform (5 x 20 ml). The extract was dried over magnesium sulfate and evaporated under reduced pressure to get N-propylbenzimidazole (1) as a thick yellowish fluid (2.81 g, 88%). Then, a mixture of 1 (1.60 g, 10 mmol) and 1,2-bis(bromomethyl)benzene (1.32 g, 5 mmol) in dioxane (30 ml) was refluxed at 90 °C for 12 h. Desired compound (2.2Br) appeared as white precipitates in the light-brown solution. The mixture was filtered and the precipitates were washed with fresh dioxane (3 x 5 ml), dried at room temperature for 24 h, and soft lumps so obtained were ground to fine powder (2.92 g, 63%). Saturated solution of 2.2Br in methanol (0.5 ml) was exposed to diethyl ether vapours at room temperature overnight to get single crystals suitable for X-ray diffraction study.

Refinement top

Atoms H1W1 and H2W1 were located from the difference Fourier map and then fixed at their found location using riding model with Uiso(H) = 1.5Ueq(O) [O—H = 0.8200 and 0.8199 Å]. The remaining H atoms were positioned geometrically [C—H = 0.93, 0.96 or 0.97 Å] and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating group model was applied to the methyl group. The 3,3'-[1,2-phenylenebis(methylene)]bis(1-propyl-benzimidazolium) cation and bromine anion are each disordered over two positions with site-occupancy ratios of 0.751 (6):0.249 (6) and 0.680 (8):0.320 (8), respectively. The SAME restraint was employed in the refinement of the disordered components. The same Uij parameters were used for atoms pairs C1X/C2X, C16X/C17X and C27/C28X. Several outlying reflections, i.e. (1 3 2), (1 2 4), (4 5 4), (4 5 3), (5 6 2) and (1 7 4), were omitted owing to poor agreement. No significant role for the water molecule was found in the crystal structure although a close H1W1···Br2X contact of 2.08 Å is noted with a disordered Br atom.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labels and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound. Only the major disordered component is shown. Intermolecular hydrogen bonds are shown as dashed lines and those hydrogen atoms which are not involved in hydrogen bonding are omitted for clarity.
3,3'-[1,2-Phenylenebis(methylene)]bis(1-propylbenzimidazolium) dibromide hemihydrate top
Crystal data top
C28H32N42+·2Br·0.5H2OZ = 2
Mr = 593.40F(000) = 606
Triclinic, P1Dx = 1.457 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0465 (4) ÅCell parameters from 9923 reflections
b = 11.4348 (5) Åθ = 2.6–29.8°
c = 14.4143 (7) ŵ = 3.02 mm1
α = 74.013 (1)°T = 296 K
β = 82.935 (1)°Block, colourless
γ = 70.817 (1)°0.54 × 0.44 × 0.26 mm
V = 1352.96 (11) Å3
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
10937 independent reflections
Radiation source: fine-focus sealed tube6959 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ϕ and ω scansθmax = 34.2°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1414
Tmin = 0.290, Tmax = 0.505k = 1718
39695 measured reflectionsl = 2222
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0782P)2]
where P = (Fo2 + 2Fc2)/3
10937 reflections(Δ/σ)max = 0.001
601 parametersΔρmax = 0.58 e Å3
86 restraintsΔρmin = 0.47 e Å3
Crystal data top
C28H32N42+·2Br·0.5H2Oγ = 70.817 (1)°
Mr = 593.40V = 1352.96 (11) Å3
Triclinic, P1Z = 2
a = 9.0465 (4) ÅMo Kα radiation
b = 11.4348 (5) ŵ = 3.02 mm1
c = 14.4143 (7) ÅT = 296 K
α = 74.013 (1)°0.54 × 0.44 × 0.26 mm
β = 82.935 (1)°
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
10937 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
6959 reflections with I > 2σ(I)
Tmin = 0.290, Tmax = 0.505Rint = 0.033
39695 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04186 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.01Δρmax = 0.58 e Å3
10937 reflectionsΔρmin = 0.47 e Å3
601 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
xyzUiso*/UeqOcc. (<1)
Br10.34759 (2)0.131872 (19)0.145379 (13)0.05001 (8)
Br20.20091 (16)0.6376 (2)0.43458 (14)0.0731 (2)0.680 (8)
Br2X0.2357 (6)0.6020 (5)0.41783 (18)0.0640 (8)0.320 (8)
O1W0.5457 (4)0.4487 (4)0.3898 (2)0.0707 (9)0.50
H1W10.46290.47710.41820.106*0.50
H2W10.58400.50510.36090.106*0.50
N10.6263 (10)0.2132 (5)0.8777 (5)0.0323 (10)0.751 (6)
N20.7191 (8)0.1608 (5)1.0205 (4)0.0353 (9)0.751 (6)
N30.3066 (7)0.2152 (6)0.5574 (4)0.0406 (11)0.751 (6)
N40.1791 (3)0.1979 (4)0.4466 (2)0.0414 (6)0.751 (6)
C10.3017 (6)0.2661 (11)0.7142 (3)0.0332 (10)0.751 (6)
C20.1394 (6)0.2895 (9)0.7207 (4)0.0468 (15)0.751 (6)
H2A0.08570.30110.66630.056*0.751 (6)
C30.0599 (7)0.2953 (12)0.8070 (5)0.062 (2)0.751 (6)
H3A0.04820.31290.81100.074*0.751 (6)
C40.1387 (7)0.2754 (9)0.8864 (5)0.065 (2)0.751 (6)
H4A0.08300.28010.94470.078*0.751 (6)
C50.2999 (6)0.2483 (8)0.8838 (3)0.0408 (17)0.751 (6)
H5A0.35160.23360.93980.049*0.751 (6)
C60.3839 (6)0.2434 (8)0.7963 (3)0.0291 (14)0.751 (6)
C70.5607 (4)0.2105 (8)0.7909 (4)0.0323 (11)0.751 (6)
H7A0.60590.12570.77980.039*0.751 (6)
H7B0.59070.27050.73600.039*0.751 (6)
C80.6449 (9)0.3233 (5)0.8918 (5)0.0308 (10)0.751 (6)
C90.6122 (10)0.4465 (6)0.8342 (6)0.0428 (13)0.751 (6)
H9A0.57590.46810.77220.051*0.751 (6)
C100.6362 (11)0.5361 (8)0.8731 (6)0.063 (2)0.751 (6)
H10A0.60810.62120.83820.075*0.751 (6)
C110.7012 (16)0.5028 (7)0.9630 (7)0.058 (2)0.751 (6)
H11A0.72710.56370.98350.070*0.751 (6)
C120.7274 (6)0.3828 (5)1.0213 (3)0.0413 (9)0.751 (6)
H12A0.75900.36341.08420.050*0.751 (6)
C130.7053 (12)0.2882 (6)0.9837 (5)0.0355 (14)0.751 (6)
C140.6661 (9)0.1196 (6)0.9572 (4)0.0346 (12)0.751 (6)
H14A0.65830.03790.96730.042*0.751 (6)
C150.7712 (8)0.0843 (10)1.1177 (5)0.0462 (15)0.751 (6)
H15A0.75190.00261.13060.055*0.751 (6)
H15B0.71150.12851.16540.055*0.751 (6)
C160.9454 (6)0.0619 (7)1.1263 (4)0.0479 (13)0.751 (6)
H16A1.00630.00941.08380.058*0.751 (6)
H16B0.96710.14311.10710.058*0.751 (6)
C170.9910 (10)0.0049 (10)1.2302 (5)0.0598 (17)0.751 (6)
H17A1.10160.02321.23520.090*0.751 (6)
H17B0.96510.08331.24970.090*0.751 (6)
H17C0.93520.04981.27150.090*0.751 (6)
C180.3809 (7)0.2683 (9)0.6143 (4)0.0477 (14)0.751 (6)
H18A0.37460.35570.58030.057*0.751 (6)
H18B0.49080.21880.62100.057*0.751 (6)
C190.3297 (11)0.0853 (6)0.5715 (5)0.0409 (10)0.751 (6)
C200.4148 (6)0.0197 (5)0.6376 (4)0.0501 (10)0.751 (6)
H20A0.47370.01240.68310.060*0.751 (6)
C210.4078 (5)0.1384 (5)0.6326 (3)0.0627 (10)0.751 (6)
H21A0.46010.21200.67750.075*0.751 (6)
C220.3234 (6)0.1483 (5)0.5615 (4)0.0636 (12)0.751 (6)
H22A0.32470.22900.55880.076*0.751 (6)
C230.2397 (6)0.0436 (5)0.4960 (4)0.0533 (11)0.751 (6)
H23A0.18180.05050.44980.064*0.751 (6)
C240.2454 (5)0.0750 (4)0.5021 (2)0.0405 (7)0.751 (6)
C250.2186 (5)0.2804 (4)0.4814 (3)0.0419 (7)0.751 (6)
H25A0.18930.36860.45640.050*0.751 (6)
C260.0792 (3)0.2281 (3)0.36446 (18)0.0526 (8)0.751 (6)
H26A0.13720.18010.31850.063*0.751 (6)
H26B0.01150.19940.38780.063*0.751 (6)
C270.0247 (6)0.3644 (4)0.3139 (3)0.0668 (10)0.751 (6)
H27A0.11370.39430.28830.080*0.751 (6)
H27B0.03480.41410.35850.080*0.751 (6)
C280.0789 (6)0.3819 (7)0.2310 (4)0.0825 (17)0.751 (6)
H28A0.17780.44530.23660.124*0.751 (6)
H28B0.09570.30210.23440.124*0.751 (6)
H28C0.02780.40900.17030.124*0.751 (6)
N1X0.616 (3)0.2328 (16)0.8647 (14)0.030 (3)0.249 (6)
N2X0.712 (3)0.1779 (16)1.0092 (12)0.048 (4)0.249 (6)
N3X0.332 (2)0.2288 (16)0.5494 (11)0.033 (2)0.249 (6)
N4X0.2008 (10)0.2460 (10)0.4266 (6)0.0447 (19)0.249 (6)
C1X0.289 (2)0.280 (4)0.7097 (12)0.045 (4)0.249 (6)
C2X0.131 (2)0.313 (3)0.7235 (11)0.045 (4)0.249 (6)
H2XA0.06850.34550.66980.054*0.249 (6)
C3X0.0585 (18)0.302 (3)0.8143 (10)0.044 (5)0.249 (6)
H3XA0.04920.31620.82010.053*0.249 (6)
C4X0.1405 (12)0.2703 (18)0.8960 (10)0.029 (3)0.249 (6)
H4XA0.09120.26870.95670.035*0.249 (6)
C5X0.3064 (14)0.240 (2)0.8822 (10)0.048 (6)0.249 (6)
H5XA0.36870.21370.93540.058*0.249 (6)
C6X0.3755 (16)0.249 (3)0.7906 (10)0.040 (6)0.249 (6)
C7X0.5551 (18)0.214 (3)0.7805 (14)0.043 (5)0.249 (6)
H7XA0.60010.12590.77710.052*0.249 (6)
H7XB0.58470.26820.72140.052*0.249 (6)
C8X0.622 (3)0.3458 (13)0.8809 (14)0.025 (2)0.249 (6)
C9X0.588 (3)0.4690 (14)0.8238 (16)0.028 (2)0.249 (6)
H9XA0.53220.49630.76750.033*0.249 (6)
C10X0.644 (2)0.5502 (16)0.8580 (13)0.034 (2)0.249 (6)
H10B0.63830.63120.81920.041*0.249 (6)
C11X0.706 (5)0.512 (2)0.9476 (18)0.054 (7)0.249 (6)
H11B0.71690.57350.97420.065*0.249 (6)
C12X0.7528 (18)0.3874 (17)0.9997 (9)0.044 (3)0.249 (6)
H12B0.82410.35761.04860.053*0.249 (6)
C13X0.683 (3)0.3077 (16)0.9728 (15)0.026 (2)0.249 (6)
C14X0.678 (3)0.1349 (15)0.9396 (10)0.026 (2)0.249 (6)
H14B0.69530.04920.94260.031*0.249 (6)
C15X0.760 (2)0.106 (3)1.1083 (13)0.040 (4)0.249 (6)
H15C0.70750.04061.12930.048*0.249 (6)
H15D0.72040.16391.14980.048*0.249 (6)
C16X0.931 (2)0.041 (2)1.1260 (13)0.049 (3)0.249 (6)
H16C0.98880.09571.08610.058*0.249 (6)
H16D0.96290.03781.10520.058*0.249 (6)
C17X0.977 (3)0.009 (3)1.2318 (13)0.049 (3)0.249 (6)
H17D1.08590.03931.23750.073*0.249 (6)
H17E0.91540.04051.27280.073*0.249 (6)
H17F0.95810.08691.25090.073*0.249 (6)
C18X0.385 (2)0.285 (3)0.6152 (12)0.059 (6)0.249 (6)
H18C0.37720.37290.58340.071*0.249 (6)
H18D0.49410.23840.62870.071*0.249 (6)
C19X0.317 (3)0.1102 (16)0.5559 (15)0.048 (5)0.249 (6)
C20X0.3762 (18)0.0076 (15)0.6166 (13)0.062 (4)0.249 (6)
H20B0.42660.01600.67170.074*0.249 (6)
C21X0.3613 (18)0.1175 (13)0.5957 (10)0.069 (4)0.249 (6)
H21B0.40400.19830.63590.082*0.249 (6)
C22X0.2820 (16)0.1025 (15)0.5145 (13)0.061 (4)0.249 (6)
H22B0.27010.17420.50150.073*0.249 (6)
C23X0.2211 (12)0.0149 (13)0.4533 (11)0.058 (3)0.249 (6)
H23B0.17060.02350.39830.070*0.249 (6)
C24X0.2365 (14)0.1207 (10)0.4751 (8)0.037 (2)0.249 (6)
C25X0.2511 (14)0.3105 (12)0.4735 (9)0.048 (3)0.249 (6)
H25B0.23300.39850.45610.057*0.249 (6)
C26X0.1198 (10)0.3095 (10)0.3319 (5)0.053 (2)0.249 (6)
H26C0.13400.39320.30680.064*0.249 (6)
H26D0.16910.25900.28590.064*0.249 (6)
C27X0.0422 (12)0.3242 (15)0.3394 (8)0.076 (3)0.249 (6)
H27C0.09190.38350.37910.091*0.249 (6)
H27D0.05540.24220.37380.091*0.249 (6)
C28X0.1297 (18)0.370 (2)0.2470 (12)0.076 (3)0.249 (6)
H28D0.22370.34620.25840.114*0.249 (6)
H28E0.06490.33260.19840.114*0.249 (6)
H28F0.15630.46180.22560.114*0.249 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.06026 (12)0.04747 (12)0.04622 (11)0.02155 (9)0.00117 (8)0.01236 (8)
Br20.0514 (3)0.1019 (5)0.0664 (4)0.0187 (4)0.0086 (2)0.0250 (5)
Br2X0.0688 (11)0.0842 (15)0.0438 (6)0.0383 (10)0.0028 (6)0.0058 (5)
O1W0.0696 (19)0.071 (2)0.0677 (19)0.0031 (17)0.0239 (15)0.0253 (17)
N10.0333 (18)0.035 (2)0.031 (2)0.0109 (19)0.0093 (12)0.0079 (19)
N20.0299 (16)0.0447 (17)0.0320 (16)0.0112 (14)0.0050 (13)0.0093 (15)
N30.037 (2)0.062 (2)0.0303 (13)0.0243 (14)0.0014 (14)0.0140 (13)
N40.0440 (13)0.056 (2)0.0321 (11)0.0230 (13)0.0038 (9)0.0141 (13)
C10.0260 (12)0.043 (3)0.0333 (16)0.0110 (13)0.0001 (12)0.0139 (17)
C20.0289 (14)0.063 (4)0.054 (2)0.0108 (15)0.0045 (12)0.0249 (19)
C30.032 (3)0.087 (5)0.075 (4)0.015 (3)0.004 (2)0.035 (3)
C40.057 (3)0.081 (5)0.055 (3)0.017 (3)0.019 (2)0.028 (3)
C50.043 (3)0.054 (3)0.0253 (16)0.015 (2)0.0067 (15)0.0135 (18)
C60.031 (2)0.034 (3)0.0238 (15)0.0086 (17)0.0060 (14)0.0087 (15)
C70.0235 (15)0.044 (3)0.0308 (18)0.0091 (14)0.0001 (12)0.0141 (16)
C80.023 (3)0.032 (2)0.0346 (18)0.003 (2)0.0052 (13)0.0078 (14)
C90.038 (3)0.037 (3)0.045 (2)0.000 (2)0.0073 (16)0.007 (2)
C100.069 (3)0.044 (3)0.076 (4)0.025 (2)0.014 (2)0.014 (2)
C110.057 (3)0.066 (5)0.072 (4)0.026 (4)0.006 (3)0.044 (3)
C120.0401 (19)0.0617 (19)0.036 (2)0.0250 (15)0.0103 (14)0.0278 (16)
C130.025 (3)0.047 (3)0.0335 (19)0.006 (2)0.0060 (13)0.0138 (19)
C140.0310 (17)0.0408 (19)0.031 (2)0.0164 (14)0.0028 (18)0.0002 (14)
C150.042 (2)0.060 (3)0.0313 (18)0.0149 (19)0.0085 (14)0.0015 (18)
C160.0298 (13)0.073 (3)0.0413 (16)0.0172 (17)0.0036 (11)0.0129 (18)
C170.053 (3)0.069 (3)0.052 (2)0.012 (2)0.0166 (17)0.008 (2)
C180.046 (2)0.081 (3)0.036 (2)0.037 (2)0.0074 (16)0.027 (2)
C190.039 (2)0.054 (2)0.0310 (17)0.016 (2)0.0008 (13)0.0121 (18)
C200.042 (3)0.065 (2)0.0364 (16)0.0147 (16)0.0010 (14)0.0046 (13)
C210.063 (2)0.062 (3)0.047 (2)0.0124 (18)0.0070 (15)0.0001 (17)
C220.070 (3)0.063 (3)0.061 (3)0.028 (2)0.017 (2)0.018 (2)
C230.055 (2)0.062 (3)0.050 (2)0.025 (2)0.0036 (18)0.019 (2)
C240.0387 (12)0.049 (2)0.0324 (15)0.0130 (17)0.0011 (12)0.0088 (14)
C250.0417 (17)0.056 (2)0.0315 (12)0.0183 (13)0.0068 (11)0.0109 (12)
C260.0545 (14)0.0700 (19)0.0407 (12)0.0213 (14)0.0154 (10)0.0170 (13)
C270.080 (3)0.072 (2)0.0559 (18)0.030 (2)0.0285 (18)0.0083 (16)
C280.098 (4)0.081 (3)0.071 (3)0.024 (3)0.052 (3)0.006 (2)
N1X0.025 (3)0.026 (4)0.027 (4)0.001 (3)0.010 (3)0.011 (3)
N2X0.043 (6)0.059 (8)0.028 (4)0.015 (5)0.018 (3)0.016 (4)
N3X0.023 (4)0.055 (5)0.030 (4)0.024 (3)0.003 (3)0.011 (3)
N4X0.040 (3)0.061 (6)0.041 (4)0.022 (4)0.003 (3)0.016 (4)
C1X0.048 (6)0.049 (8)0.040 (5)0.015 (5)0.016 (4)0.008 (4)
C2X0.048 (6)0.049 (8)0.040 (5)0.015 (5)0.016 (4)0.008 (4)
C3X0.028 (8)0.061 (10)0.040 (7)0.013 (7)0.022 (6)0.016 (6)
C4X0.014 (4)0.054 (8)0.024 (4)0.017 (4)0.003 (3)0.010 (4)
C5X0.025 (6)0.050 (9)0.075 (11)0.013 (6)0.019 (6)0.014 (7)
C6X0.021 (6)0.038 (9)0.066 (11)0.015 (5)0.016 (5)0.018 (8)
C7X0.057 (8)0.053 (10)0.031 (5)0.020 (6)0.022 (4)0.017 (5)
C8X0.016 (5)0.024 (5)0.029 (4)0.008 (4)0.014 (3)0.010 (4)
C9X0.026 (5)0.012 (4)0.036 (4)0.005 (4)0.015 (3)0.002 (3)
C10X0.042 (5)0.034 (6)0.036 (4)0.021 (4)0.002 (4)0.011 (4)
C11X0.077 (15)0.044 (10)0.044 (6)0.028 (10)0.003 (7)0.003 (6)
C12X0.035 (5)0.076 (8)0.025 (5)0.017 (4)0.017 (3)0.026 (5)
C13X0.018 (6)0.022 (4)0.033 (5)0.000 (4)0.008 (3)0.003 (3)
C14X0.033 (4)0.032 (5)0.019 (4)0.022 (4)0.007 (3)0.006 (4)
C15X0.023 (4)0.061 (9)0.031 (5)0.019 (5)0.005 (3)0.006 (4)
C16X0.049 (5)0.071 (7)0.033 (4)0.033 (5)0.013 (3)0.000 (4)
C17X0.049 (5)0.071 (7)0.033 (4)0.033 (5)0.013 (3)0.000 (4)
C18X0.069 (10)0.071 (10)0.047 (8)0.022 (7)0.026 (7)0.019 (7)
C19X0.033 (6)0.058 (8)0.045 (8)0.011 (6)0.009 (5)0.005 (5)
C20X0.031 (6)0.096 (11)0.059 (10)0.023 (6)0.005 (5)0.019 (8)
C21X0.071 (10)0.054 (7)0.050 (8)0.006 (7)0.023 (7)0.010 (7)
C22X0.058 (8)0.061 (10)0.061 (9)0.019 (7)0.010 (6)0.016 (8)
C23X0.045 (4)0.071 (8)0.077 (7)0.021 (5)0.004 (5)0.046 (7)
C24X0.044 (4)0.031 (5)0.033 (5)0.004 (5)0.010 (4)0.009 (4)
C25X0.039 (5)0.063 (7)0.053 (5)0.022 (4)0.001 (4)0.025 (5)
C26X0.051 (4)0.068 (6)0.040 (4)0.015 (4)0.001 (3)0.019 (4)
C27X0.066 (5)0.090 (8)0.063 (5)0.002 (5)0.023 (4)0.028 (5)
C28X0.066 (5)0.090 (8)0.063 (5)0.002 (5)0.023 (4)0.028 (5)
Geometric parameters (Å, º) top
O1W—H1W10.8199C28—H28C0.9600
O1W—H2W10.8200N1X—C14X1.343 (13)
N1—C141.328 (6)N1X—C8X1.393 (13)
N1—C81.394 (5)N1X—C7X1.484 (13)
N1—C71.461 (5)N2X—C14X1.337 (13)
N2—C141.333 (5)N2X—C13X1.377 (13)
N2—C131.374 (6)N2X—C15X1.477 (13)
N2—C151.473 (6)N3X—C25X1.337 (13)
N3—C251.329 (5)N3X—C19X1.385 (13)
N3—C191.390 (6)N3X—C18X1.478 (14)
N3—C181.473 (5)N4X—C25X1.334 (11)
N4—C251.340 (4)N4X—C24X1.359 (11)
N4—C241.386 (4)N4X—C26X1.510 (10)
N4—C261.473 (3)C1X—C2X1.362 (13)
C1—C61.392 (4)C1X—C6X1.382 (13)
C1—C21.400 (4)C1X—C18X1.520 (14)
C1—C181.526 (4)C2X—C3X1.382 (13)
C2—C31.364 (6)C2X—H2XA0.9300
C2—H2A0.9300C3X—C4X1.368 (13)
C3—C41.349 (7)C3X—H3XA0.9300
C3—H3A0.9300C4X—C5X1.426 (11)
C4—C51.386 (6)C4X—H4XA0.9300
C4—H4A0.9300C5X—C6X1.382 (13)
C5—C61.395 (4)C5X—H5XA0.9300
C5—H5A0.9300C6X—C7X1.539 (13)
C6—C71.516 (4)C7X—H7XA0.9700
C7—H7A0.9700C7X—H7XB0.9700
C7—H7B0.9700C8X—C9X1.377 (13)
C8—C91.380 (6)C8X—C13X1.399 (13)
C8—C131.398 (6)C9X—C10X1.408 (12)
C9—C101.379 (7)C9X—H9XA0.9300
C9—H9A0.9300C10X—C11X1.372 (14)
C10—C111.393 (7)C10X—H10B0.9300
C10—H10A0.9300C11X—C12X1.362 (15)
C11—C121.359 (6)C11X—H11B0.9300
C11—H11A0.9300C12X—C13X1.418 (14)
C12—C131.413 (5)C12X—H12B0.9300
C12—H12A0.9300C14X—H14B0.9300
C14—H14A0.9300C15X—C16X1.497 (15)
C15—C161.526 (6)C15X—H15C0.9700
C15—H15A0.9700C15X—H15D0.9700
C15—H15B0.9700C16X—C17X1.543 (14)
C16—C171.521 (6)C16X—H16C0.9700
C16—H16A0.9700C16X—H16D0.9700
C16—H16B0.9700C17X—H17D0.9600
C17—H17A0.9600C17X—H17E0.9600
C17—H17B0.9600C17X—H17F0.9600
C17—H17C0.9600C18X—H18C0.9700
C18—H18A0.9700C18X—H18D0.9700
C18—H18B0.9700C19X—C20X1.364 (14)
C19—C201.373 (6)C19X—C24X1.403 (13)
C19—C241.381 (5)C20X—C21X1.420 (15)
C20—C211.402 (6)C20X—H20B0.9300
C20—H20A0.9300C21X—C22X1.390 (15)
C21—C221.400 (6)C21X—H21B0.9300
C21—H21A0.9300C22X—C23X1.365 (14)
C22—C231.362 (6)C22X—H22B0.9300
C22—H22A0.9300C23X—C24X1.384 (11)
C23—C241.402 (6)C23X—H23B0.9300
C23—H23A0.9300C25X—H25B0.9300
C25—H25A0.9300C26X—C27X1.413 (12)
C26—C271.470 (5)C26X—H26C0.9700
C26—H26A0.9700C26X—H26D0.9700
C26—H26B0.9700C27X—C28X1.509 (13)
C27—C281.538 (4)C27X—H27C0.9700
C27—H27A0.9700C27X—H27D0.9700
C27—H27B0.9700C28X—H28D0.9600
C28—H28A0.9600C28X—H28E0.9600
C28—H28B0.9600C28X—H28F0.9600
H1W1—O1W—H2W1111.9C25X—N3X—C19X107.1 (11)
C14—N1—C8108.7 (4)C25X—N3X—C18X116.9 (14)
C14—N1—C7127.8 (5)C19X—N3X—C18X134.5 (15)
C8—N1—C7123.3 (5)C25X—N4X—C24X110.4 (8)
C14—N2—C13109.3 (4)C25X—N4X—C26X122.1 (10)
C14—N2—C15124.9 (6)C24X—N4X—C26X127.5 (8)
C13—N2—C15125.6 (5)C2X—C1X—C6X116.5 (12)
C25—N3—C19109.4 (4)C2X—C1X—C18X128.5 (14)
C25—N3—C18126.4 (5)C6X—C1X—C18X114.6 (13)
C19—N3—C18124.0 (5)C1X—C2X—C3X122.5 (14)
C25—N4—C24108.9 (3)C1X—C2X—H2XA118.8
C25—N4—C26127.4 (3)C3X—C2X—H2XA118.8
C24—N4—C26123.7 (3)C4X—C3X—C2X122.0 (13)
C6—C1—C2120.3 (4)C4X—C3X—H3XA119.0
C6—C1—C18122.8 (4)C2X—C3X—H3XA119.0
C2—C1—C18116.9 (4)C3X—C4X—C5X115.8 (11)
C3—C2—C1120.0 (5)C3X—C4X—H4XA122.1
C3—C2—H2A120.0C5X—C4X—H4XA122.1
C1—C2—H2A120.0C6X—C5X—C4X120.7 (11)
C4—C3—C2119.9 (5)C6X—C5X—H5XA119.7
C4—C3—H3A120.1C4X—C5X—H5XA119.7
C2—C3—H3A120.1C1X—C6X—C5X121.9 (11)
C3—C4—C5122.0 (6)C1X—C6X—C7X119.8 (12)
C3—C4—H4A119.0C5X—C6X—C7X118.2 (12)
C5—C4—H4A119.0N1X—C7X—C6X109.7 (14)
C4—C5—C6119.4 (4)N1X—C7X—H7XA109.7
C4—C5—H5A120.3C6X—C7X—H7XA109.7
C6—C5—H5A120.3N1X—C7X—H7XB109.7
C1—C6—C5118.4 (4)C6X—C7X—H7XB109.7
C1—C6—C7120.6 (4)H7XA—C7X—H7XB108.2
C5—C6—C7121.0 (4)C9X—C8X—N1X132.2 (13)
N1—C7—C6113.7 (4)C9X—C8X—C13X123.7 (12)
N1—C7—H7A108.8N1X—C8X—C13X104.0 (11)
C6—C7—H7A108.8C8X—C9X—C10X114.3 (13)
N1—C7—H7B108.8C8X—C9X—H9XA122.8
C6—C7—H7B108.8C10X—C9X—H9XA122.8
H7A—C7—H7B107.7C11X—C10X—C9X121.0 (15)
C9—C8—N1131.6 (5)C11X—C10X—H10B119.5
C9—C8—C13122.4 (5)C9X—C10X—H10B119.5
N1—C8—C13106.0 (4)C12X—C11X—C10X123.7 (17)
C10—C9—C8116.7 (6)C12X—C11X—H11B118.2
C10—C9—H9A121.7C10X—C11X—H11B118.2
C8—C9—H9A121.7C11X—C12X—C13X114.0 (15)
C9—C10—C11122.0 (6)C11X—C12X—H12B123.0
C9—C10—H10A119.0C13X—C12X—H12B123.0
C11—C10—H10A119.0N2X—C13X—C8X109.8 (11)
C12—C11—C10121.0 (5)N2X—C13X—C12X127.4 (15)
C12—C11—H11A119.5C8X—C13X—C12X118.9 (13)
C10—C11—H11A119.5N2X—C14X—N1X110.5 (12)
C11—C12—C13118.2 (5)N2X—C14X—H14B124.7
C11—C12—H12A120.9N1X—C14X—H14B124.7
C13—C12—H12A120.9N2X—C15X—C16X118.6 (16)
N2—C13—C8106.4 (4)N2X—C15X—H15C107.7
N2—C13—C12134.2 (5)C16X—C15X—H15C107.7
C8—C13—C12119.2 (5)N2X—C15X—H15D107.7
N1—C14—N2109.4 (5)C16X—C15X—H15D107.7
N1—C14—H14A125.3H15C—C15X—H15D107.1
N2—C14—H14A125.3C15X—C16X—C17X115.2 (16)
N2—C15—C16110.8 (6)C15X—C16X—H16C108.5
N2—C15—H15A109.5C17X—C16X—H16C108.5
C16—C15—H15A109.5C15X—C16X—H16D108.5
N2—C15—H15B109.5C17X—C16X—H16D108.5
C16—C15—H15B109.5H16C—C16X—H16D107.5
H15A—C15—H15B108.1C16X—C17X—H17D109.5
C17—C16—C15109.3 (5)C16X—C17X—H17E109.5
C17—C16—H16A109.8H17D—C17X—H17E109.5
C15—C16—H16A109.8C16X—C17X—H17F109.5
C17—C16—H16B109.8H17D—C17X—H17F109.5
C15—C16—H16B109.8H17E—C17X—H17F109.5
H16A—C16—H16B108.3N3X—C18X—C1X112.2 (16)
N3—C18—C1111.4 (5)N3X—C18X—H18C109.2
N3—C18—H18A109.4C1X—C18X—H18C109.2
C1—C18—H18A109.4N3X—C18X—H18D109.2
N3—C18—H18B109.4C1X—C18X—H18D109.2
C1—C18—H18B109.4H18C—C18X—H18D107.9
H18A—C18—H18B108.0C20X—C19X—N3X132.9 (13)
C20—C19—C24122.3 (4)C20X—C19X—C24X118.9 (12)
C20—C19—N3131.5 (4)N3X—C19X—C24X107.8 (11)
C24—C19—N3106.2 (5)C19X—C20X—C21X120.0 (13)
C19—C20—C21116.1 (4)C19X—C20X—H20B120.0
C19—C20—H20A122.0C21X—C20X—H20B120.0
C21—C20—H20A122.0C22X—C21X—C20X119.1 (12)
C22—C21—C20121.3 (4)C22X—C21X—H21B120.4
C22—C21—H21A119.3C20X—C21X—H21B120.4
C20—C21—H21A119.3C23X—C22X—C21X121.5 (12)
C23—C22—C21122.1 (4)C23X—C22X—H22B119.2
C23—C22—H22A118.9C21X—C22X—H22B119.2
C21—C22—H22A118.9C22X—C23X—C24X118.4 (11)
C22—C23—C24116.3 (4)C22X—C23X—H23B120.8
C22—C23—H23A121.8C24X—C23X—H23B120.8
C24—C23—H23A121.8N4X—C24X—C23X132.6 (10)
C19—C24—N4106.8 (4)N4X—C24X—C19X105.0 (9)
C19—C24—C23121.8 (4)C23X—C24X—C19X122.0 (11)
N4—C24—C23131.4 (3)N4X—C25X—N3X109.3 (11)
N3—C25—N4108.7 (4)N4X—C25X—H25B125.3
N3—C25—H25A125.7N3X—C25X—H25B125.3
N4—C25—H25A125.7C27X—C26X—N4X113.5 (8)
C27—C26—N4114.6 (3)C27X—C26X—H26C108.9
C27—C26—H26A108.6N4X—C26X—H26C108.9
N4—C26—H26A108.6C27X—C26X—H26D108.9
C27—C26—H26B108.6N4X—C26X—H26D108.9
N4—C26—H26B108.6H26C—C26X—H26D107.7
H26A—C26—H26B107.6C26X—C27X—C28X117.7 (11)
C26—C27—C28109.0 (3)C26X—C27X—H27C107.9
C26—C27—H27A109.9C28X—C27X—H27C107.9
C28—C27—H27A109.9C26X—C27X—H27D107.9
C26—C27—H27B109.9C28X—C27X—H27D107.9
C28—C27—H27B109.9H27C—C27X—H27D107.2
H27A—C27—H27B108.3C27X—C28X—H28D109.5
C14X—N1X—C8X109.0 (11)C27X—C28X—H28E109.5
C14X—N1X—C7X122.3 (15)H28D—C28X—H28E109.5
C8X—N1X—C7X128.7 (15)C27X—C28X—H28F109.5
C14X—N2X—C13X106.3 (12)H28D—C28X—H28F109.5
C14X—N2X—C15X128.1 (16)H28E—C28X—H28F109.5
C13X—N2X—C15X125.4 (16)
C6—C1—C2—C32.7 (12)C6X—C1X—C2X—C3X8 (4)
C18—C1—C2—C3176.8 (11)C18X—C1X—C2X—C3X179 (4)
C1—C2—C3—C41.6 (16)C1X—C2X—C3X—C4X8 (4)
C2—C3—C4—C50.3 (18)C2X—C3X—C4X—C5X5 (4)
C3—C4—C5—C61.1 (15)C3X—C4X—C5X—C6X3 (3)
C2—C1—C6—C51.9 (12)C2X—C1X—C6X—C5X6 (4)
C18—C1—C6—C5177.5 (9)C18X—C1X—C6X—C5X180 (3)
C2—C1—C6—C7176.4 (7)C2X—C1X—C6X—C7X178 (2)
C18—C1—C6—C74.1 (14)C18X—C1X—C6X—C7X4 (4)
C4—C5—C6—C10.0 (13)C4X—C5X—C6X—C1X4 (4)
C4—C5—C6—C7178.3 (8)C4X—C5X—C6X—C7X180 (2)
C14—N1—C7—C686.5 (11)C14X—N1X—C7X—C6X100 (3)
C8—N1—C7—C688.0 (10)C8X—N1X—C7X—C6X80 (3)
C1—C6—C7—N1169.1 (8)C1X—C6X—C7X—N1X159 (3)
C5—C6—C7—N112.7 (11)C5X—C6X—C7X—N1X25 (3)
C14—N1—C8—C9176.2 (10)C14X—N1X—C8X—C9X173 (3)
C7—N1—C8—C90.7 (15)C7X—N1X—C8X—C9X7 (5)
C14—N1—C8—C132.6 (10)C14X—N1X—C8X—C13X3 (3)
C7—N1—C8—C13178.0 (8)C7X—N1X—C8X—C13X177 (3)
N1—C8—C9—C10176.1 (10)N1X—C8X—C9X—C10X165 (3)
C13—C8—C9—C102.5 (14)C13X—C8X—C9X—C10X10 (4)
C8—C9—C10—C114.7 (16)C8X—C9X—C10X—C11X9 (4)
C9—C10—C11—C127.6 (19)C9X—C10X—C11X—C12X16 (6)
C10—C11—C12—C137.7 (16)C10X—C11X—C12X—C13X22 (5)
C14—N2—C13—C81.9 (10)C14X—N2X—C13X—C8X4 (3)
C15—N2—C13—C8177.0 (7)C15X—N2X—C13X—C8X173 (2)
C14—N2—C13—C12172.6 (10)C14X—N2X—C13X—C12X154 (3)
C15—N2—C13—C122.5 (16)C15X—N2X—C13X—C12X30 (5)
C9—C8—C13—N2178.5 (9)C9X—C8X—C13X—N2X177 (3)
N1—C8—C13—N20.4 (10)N1X—C8X—C13X—N2X0 (3)
C9—C8—C13—C123.0 (14)C9X—C8X—C13X—C12X17 (4)
N1—C8—C13—C12175.9 (8)N1X—C8X—C13X—C12X159 (2)
C11—C12—C13—N2179.4 (11)C11X—C12X—C13X—N2X177 (3)
C11—C12—C13—C85.5 (13)C11X—C12X—C13X—C8X22 (4)
C8—N1—C14—N23.8 (10)C13X—N2X—C14X—N1X6 (3)
C7—N1—C14—N2179.0 (7)C15X—N2X—C14X—N1X170 (2)
C13—N2—C14—N13.6 (10)C8X—N1X—C14X—N2X6 (3)
C15—N2—C14—N1178.7 (7)C7X—N1X—C14X—N2X175 (2)
C14—N2—C15—C16115.6 (9)C14X—N2X—C15X—C16X89 (3)
C13—N2—C15—C1670.0 (11)C13X—N2X—C15X—C16X96 (4)
N2—C15—C16—C17174.0 (8)N2X—C15X—C16X—C17X159 (2)
C25—N3—C18—C1109.2 (8)C25X—N3X—C18X—C1X106 (2)
C19—N3—C18—C176.3 (10)C19X—N3X—C18X—C1X58 (4)
C6—C1—C18—N3144.6 (9)C2X—C1X—C18X—N3X47 (4)
C2—C1—C18—N336.0 (10)C6X—C1X—C18X—N3X140 (3)
C25—N3—C19—C20177.8 (9)C25X—N3X—C19X—C20X178 (3)
C18—N3—C19—C202.4 (15)C18X—N3X—C19X—C20X17 (5)
C25—N3—C19—C242.4 (9)C25X—N3X—C19X—C24X6 (3)
C18—N3—C19—C24177.7 (5)C18X—N3X—C19X—C24X171 (2)
C24—C19—C20—C211.8 (12)N3X—C19X—C20X—C21X169 (3)
N3—C19—C20—C21178.0 (9)C24X—C19X—C20X—C21X2 (3)
C19—C20—C21—C222.5 (9)C19X—C20X—C21X—C22X2 (3)
C20—C21—C22—C232.5 (8)C20X—C21X—C22X—C23X1 (2)
C21—C22—C23—C241.5 (7)C21X—C22X—C23X—C24X1.6 (19)
C20—C19—C24—N4178.1 (7)C25X—N4X—C24X—C23X174.1 (13)
N3—C19—C24—N42.1 (8)C26X—N4X—C24X—C23X5 (2)
C20—C19—C24—C231.0 (12)C25X—N4X—C24X—C19X1.1 (18)
N3—C19—C24—C23178.8 (5)C26X—N4X—C24X—C19X177.5 (15)
C25—N4—C24—C191.1 (6)C22X—C23X—C24X—N4X174.1 (13)
C26—N4—C24—C19179.9 (5)C22X—C23X—C24X—C19X2 (2)
C25—N4—C24—C23180.0 (4)C20X—C19X—C24X—N4X176 (2)
C26—N4—C24—C231.2 (6)N3X—C19X—C24X—N4X3 (2)
C22—C23—C24—C190.8 (8)C20X—C19X—C24X—C23X2 (3)
C22—C23—C24—N4178.0 (4)N3X—C19X—C24X—C23X171.1 (16)
C19—N3—C25—N41.8 (7)C24X—N4X—C25X—N3X4.9 (15)
C18—N3—C25—N4177.0 (5)C26X—N4X—C25X—N3X173.8 (11)
C24—N4—C25—N30.4 (5)C19X—N3X—C25X—N4X7 (2)
C26—N4—C25—N3178.3 (4)C18X—N3X—C25X—N4X174.8 (14)
C25—N4—C26—C273.0 (5)C25X—N4X—C26X—C27X108.4 (13)
C24—N4—C26—C27178.4 (4)C24X—N4X—C26X—C27X73.1 (14)
N4—C26—C27—C28179.5 (3)N4X—C26X—C27X—C28X172.1 (13)
Hydrogen-bond geometry (Å, º) top
Cg6 and Cg8 are the centroids of the N1X/C8X/C13X/N2X/C14X and C1X–C6X rings, respectively.
D—H···AD—HH···AD···AD—H···A
C5—H5A···Br1i0.932.873.665 (4)144
C7—H7A···Br1ii0.972.753.596 (9)146
C14—H14A···Br1ii0.932.873.618 (7)138
C20—H20A···Br1ii0.932.873.699 (6)148
C5—H5A···Cg60.932.823.405 (14)122
C28—H28A···Cg8iii0.962.993.607 (15)123
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1; (iii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC28H32N42+·2Br·0.5H2O
Mr593.40
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)9.0465 (4), 11.4348 (5), 14.4143 (7)
α, β, γ (°)74.013 (1), 82.935 (1), 70.817 (1)
V3)1352.96 (11)
Z2
Radiation typeMo Kα
µ (mm1)3.02
Crystal size (mm)0.54 × 0.44 × 0.26
Data collection
DiffractometerBruker APEX DUO CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.290, 0.505
No. of measured, independent and
observed [I > 2σ(I)] reflections
39695, 10937, 6959
Rint0.033
(sin θ/λ)max1)0.790
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.133, 1.01
No. of reflections10937
No. of parameters601
No. of restraints86
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.58, 0.47

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg6 and Cg8 are the centroids of the N1X/C8X/C13X/N2X/C14X and C1X–C6X rings, respectively.
D—H···AD—HH···AD···AD—H···A
C5—H5A···Br1i0.932.873.665 (4)144
C7—H7A···Br1ii0.972.753.596 (9)146
C14—H14A···Br1ii0.932.873.618 (7)138
C20—H20A···Br1ii0.932.873.699 (6)148
C5—H5A···Cg60.932.823.405 (14)122
C28—H28A···Cg8iii0.962.993.607 (15)123
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1; (iii) x, y+1, z+1.
 

Footnotes

Visiting Professor, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

RAH thanks Universiti Sains Malaysia (USM) for the Research University (RU) grants (1001/PKIMIA/811157 and 1001/PKIMIA/823082). MAI is grateful to (IPS) USM for financial support [fellowship: USM·IPS/JWT/1/19 (JLD 6)] and research attachment fund [P-KM0018/10(R) − 308/AIPS/415401]. HKF and TSC thank USM for the RU grant (1001/PFIZIK/811160). TSC thanks the Malaysian Government and USM for the award of the post of Research Officer under RU grant 1001/PSKBP/8630013.

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Volume 68| Part 2| February 2012| Pages o466-o467
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