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Acta Cryst. (2009). E65, o745-o746    [ doi:10.1107/S1600536809008071 ]

2-(1H-Benzoimidazol-2-yl)-6-ethoxyphenol

C. S. Yeap, H. Kargar, R. Kia, A. Jamshidvand and H.-K. Fun

Abstract top

The title Schiff base compound, C15H14N2O2, consists of two crystallographically independent molecules, A and B. Molecule A is almost planar, whereas molecule B is slightly twisted, the dihedral angles between the benzimidazole group and the benzene rings being 2.65 (12) and 13.17 (15)°, respectively. The methyl group of molecule B is disordered over two positions, with a refined site-occupancy ratio of 0.581 (7):0.419 (7). In each molecule, intramolecular O-H...N hydrogen bonds generate S(6) ring motifs. In the crystal structure, both types of molecules are linked via intermolecular bifurcated N-H...O hydrogen bonds into one-dimensional extended chains along [010] and form R12(5) ring motifs. The crystal structure is further stabilized by intermolecular C-H...[pi] and [pi]-[pi] interactions [centroid-centroid distances = 3.4758 (16)-3.596 (2) Å].

Comment top

Benzimidazoles are used widely in biological applications and as pharmaceutical agents (Craigo et al., 1999; Gudmundsson et al., 2000; Trivedi et al., 2006). They are also used as topoisomerase I inhibitors (Kim et al., 1996) and for antitumor activity (Ramla et al., 2006). Due to these important applications, many synthetic routes towards benzimidazoles have been developed. They can, for example, be synthesized by the reaction of phenolic aldehydes with o-phenylenediamine (Latif et al.,, 1983). Based on this route the title compound was synthesized and its crystal structure is reported here.

The asymmetric unit of the title compound, Fig. 1, consists of two crystallographically independent molecules, A and B with a slightly different conformations due to a disordered group. Intramolecular O—H···N hydrogen bonds generate S(6) ring motifs (Bernstein et al., 1995). The two molecules A and B are linked together by a bifurcated hydrogen bond involving the two oxygen atoms of the hydroxy and ethoxy groups with a R12(5) ring motif. The molecule A is almost planar wheares the molecule B is slightly twisted with the dihedral angles between the benzimidazole and the phenyl rings being 2.65 (12) and 13.17 (15) °, respectively. The methyl group of molecule B is disordered over two positions with a refined site-occupancy ratio of 0.581 (7):0.419 (7). The crystal structure is further stabilized by intermolecular C—H···π [Cg1, Cg2 and Cg3 are the centroids of the C8B–C13B, C1B–C6B and N1A/C1A/C6A/N2A/C7A rings] (Table 1) and π-π interactions [Cg1···Cg4iii = 3.596 (2) and Cg3···Cg5iii = 3.4758 (16) Å; (iii) -x, y, 1/2 - z ; Cg4 and Cg5 are the centroids of the N1B/C1B/C6B/N2B/C7B and C8A–C13A rings]. In the crystal structure, molecules are linked together into 1-D extended chains along the [0 1 0] direction (Fig. 2).

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For benzimidazole chemistry, reaction mechanisms and bioactivity, see, for example: Latif et al. (1983); Craigo et al. (1999); Gudmundsson et al. (2000); Trivedi et al.(2006); Kim et al. (1996); Ramla et al. (2006). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). Cg1, Cg2 and Cg3 are the centroids of the C8B–C13B, C1B–C6B and N1A–C1A–C6A–N2A–C7A rings, respectively.

Experimental top

An ethanolic solution (50 ml) of 3-ethoxy-salicylaldehyde (2 mmol, 332 mg) was added to 1,2-phenylenediamine (1 mmol, 217 mg). The mixture was refluxed for 2 h, and cooled to room temperature. The resulting colourless powder was filtered, washed with cooled ethanol and dried in vacuo. Single crystals suitable for X-ray diffraction were obtained from an methanol solution at room temperature.

Refinement top

O1A, O1B and N-bound hydrogen atoms were located from the diffrence Fourier map and refined freely. The rest of the hydrogen atoms were positioned geometrically with a riding model approximation with C—H = 0.93-0.97 Å and Uiso(H) = 1.2 or 1.5 (C & O). A rotating group model was used for methyl group.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 50% probability ellipsoids for non-H atoms. Intra- and intermolecular hydrogen bonds are shown as dashed lines. The open bond indicates the minor component of disorder.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound with hydrogen bonds shown as dashed lines. The disorder is not shown and only H atoms involved in hydrogen bonds are drawn.
2-(1H-Benzoimidazol-2-yl)-6-ethoxyphenol top
Crystal data top
C15H14N2O2F(000) = 2144
Mr = 254.28Dx = 1.352 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9961 reflections
a = 22.5305 (4) Åθ = 2.5–32.2°
b = 12.0113 (2) ŵ = 0.09 mm−1
c = 21.4241 (3) ÅT = 100 K
β = 120.449 (1)°Block, yellow
V = 4998.17 (14) Å30.38 × 0.23 × 0.18 mm
Z = 16
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5171 independent reflections
Radiation source: fine-focus sealed tube4238 reflections with I > 2σ(I)
graphiteRint = 0.043
φ and ω scansθmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −28→28
Tmin = 0.966, Tmax = 0.984k = −14→15
49947 measured reflectionsl = −26→26
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.19 w = 1/[σ2(Fo2) + (0.022P)2 + 16.3221P]
where P = (Fo2 + 2Fc2)/3
5171 reflections(Δ/σ)max < 0.001
372 parametersΔρmax = 0.57 e Å−3
1 restraintΔρmin = −0.48 e Å−3
Crystal data top
C15H14N2O2V = 4998.17 (14) Å3
Mr = 254.28Z = 16
Monoclinic, C2/cMo Kα radiation
a = 22.5305 (4) ŵ = 0.09 mm−1
b = 12.0113 (2) ÅT = 100 K
c = 21.4241 (3) Å0.38 × 0.23 × 0.18 mm
β = 120.449 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5171 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		4238 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.984Rint = 0.043
49947 measured reflectionsθmax = 26.5°
Refinement top
R[F2 > 2σ(F2)] = 0.067 w = 1/[σ2(Fo2) + (0.022P)2 + 16.3221P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.151Δρmax = 0.57 e Å−3
S = 1.19Δρmin = −0.48 e Å−3
5171 reflectionsAbsolute structure: ?
372 parametersFlack parameter: ?
1 restraintRogers parameter: ?
H atoms treated by a mixture of independent and constrained refinement
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
O1A0.04313 (11)−0.05359 (15)0.34802 (11)0.0343 (5)
O2A−0.04669 (10)−0.05371 (16)0.38878 (11)0.0352 (5)
N1A0.12309 (11)0.04703 (18)0.31444 (12)0.0278 (5)
N2A0.12918 (13)0.2321 (2)0.31223 (14)0.0328 (5)
C1A0.16902 (14)0.0757 (2)0.29195 (14)0.0280 (6)
C2A0.20683 (15)0.0094 (2)0.27078 (16)0.0345 (6)
H2AA0.2047−0.06780.27140.041*
C3A0.24743 (16)0.0632 (3)0.24891 (17)0.0389 (7)
H3AA0.27310.02090.23460.047*
C4A0.25106 (16)0.1776 (3)0.24763 (18)0.0413 (7)
H4AA0.27920.21040.23260.050*
C5A0.21403 (16)0.2450 (3)0.26805 (17)0.0408 (7)
H5AA0.21650.32220.26700.049*
C6A0.17291 (14)0.1923 (2)0.29023 (15)0.0318 (6)
C7A0.09976 (13)0.1427 (2)0.32507 (13)0.0267 (5)
C8A0.04901 (13)0.1485 (2)0.34835 (14)0.0257 (5)
C9A0.02514 (14)0.2496 (2)0.36000 (15)0.0319 (6)
H9AA0.04240.31650.35400.038*
C10A−0.02370 (15)0.2501 (2)0.38028 (16)0.0362 (7)
H10A−0.03980.31750.38730.043*
C11A−0.04945 (14)0.1499 (2)0.39045 (15)0.0328 (6)
H11A−0.08240.15110.40430.039*
C12A−0.02616 (14)0.0499 (2)0.38002 (14)0.0290 (6)
C13A0.02312 (13)0.0480 (2)0.35843 (13)0.0255 (5)
C14A−0.09118 (15)−0.0595 (3)0.41821 (17)0.0405 (7)
H14A−0.1346−0.02300.38630.049*
H14B−0.0700−0.02370.46520.049*
C15A−0.10244 (18)−0.1825 (3)0.4250 (2)0.0546 (9)
H15A−0.1308−0.19110.44630.082*
H15B−0.0588−0.21810.45530.082*
H15C−0.1248−0.21630.37790.082*
O1B0.08605 (12)0.45323 (16)0.25795 (12)0.0409 (5)
O2B0.17852 (13)0.46703 (18)0.39287 (12)0.0530 (6)
N1B0.00726 (12)0.54159 (19)0.13347 (13)0.0332 (5)
N2B−0.01822 (12)0.72236 (19)0.12353 (13)0.0303 (5)
C1B−0.04540 (15)0.5626 (2)0.06352 (16)0.0335 (6)
C2B−0.08028 (17)0.4918 (3)0.00407 (17)0.0438 (8)
H2BA−0.06920.41660.00750.053*
C3B−0.13164 (17)0.5368 (3)−0.06005 (17)0.0461 (8)
H3BA−0.15480.4912−0.10050.055*
C4B−0.14955 (16)0.6492 (3)−0.06553 (17)0.0448 (8)
H4BA−0.18520.6762−0.10920.054*
C5B−0.11554 (16)0.7216 (3)−0.00752 (17)0.0393 (7)
H5BA−0.12740.7965−0.01120.047*
C6B−0.06268 (14)0.6763 (2)0.05654 (15)0.0313 (6)
C7B0.02231 (14)0.6394 (2)0.16742 (15)0.0295 (6)
C8B0.07626 (14)0.6529 (2)0.24254 (15)0.0286 (6)
C9B0.10079 (14)0.7581 (2)0.27454 (16)0.0303 (6)
H9BA0.08190.82240.24750.036*
C10B0.15256 (15)0.7658 (2)0.34562 (16)0.0332 (6)
H10B0.16880.83560.36600.040*
C11B0.18127 (16)0.6703 (2)0.38783 (16)0.0357 (7)
H11B0.21650.67640.43580.043*
C12B0.15684 (16)0.5670 (2)0.35757 (16)0.0368 (7)
C13B0.10542 (15)0.5578 (2)0.28474 (16)0.0319 (6)
C14B0.2276 (2)0.4683 (3)0.46948 (18)0.0576 (10)
H14C0.20900.50880.49490.069*0.581 (7)
H14D0.26980.50460.47880.069*0.581 (7)
H14E0.22180.40280.49150.069*0.419 (7)
H14F0.22080.53230.49200.069*0.419 (7)
C15B0.2415 (4)0.3527 (6)0.4943 (4)0.070 (2)0.581 (7)
H15D0.27340.35100.54560.104*0.581 (7)
H15E0.26090.31390.46970.104*0.581 (7)
H15F0.19930.31720.48410.104*0.581 (7)
C15C0.2967 (3)0.4728 (8)0.4792 (5)0.063 (3)0.419 (7)
H15G0.33030.47390.53000.095*0.419 (7)
H15H0.30120.53900.45680.095*0.419 (7)
H15I0.30390.40850.45730.095*0.419 (7)
H1OA0.0731 (18)−0.030 (3)0.3339 (18)0.052 (10)*
H1NA0.1191 (17)0.297 (3)0.3128 (18)0.048 (10)*
H1OB0.0555 (19)0.462 (3)0.206 (2)0.061 (11)*
H1NB−0.0186 (17)0.797 (3)0.1365 (18)0.052 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0431 (12)0.0193 (9)0.0518 (13)−0.0025 (8)0.0323 (11)−0.0009 (8)
O2A0.0383 (11)0.0298 (10)0.0448 (12)−0.0082 (9)0.0264 (10)−0.0019 (9)
N1A0.0325 (12)0.0206 (11)0.0335 (12)−0.0002 (9)0.0191 (10)−0.0002 (9)
N2A0.0359 (13)0.0209 (12)0.0431 (14)0.0007 (10)0.0210 (12)0.0060 (10)
C1A0.0303 (14)0.0240 (13)0.0278 (13)−0.0017 (11)0.0133 (11)0.0029 (10)
C2A0.0376 (16)0.0281 (14)0.0389 (16)0.0001 (12)0.0202 (13)0.0017 (12)
C3A0.0388 (16)0.0428 (17)0.0399 (16)0.0019 (14)0.0236 (14)0.0032 (13)
C4A0.0374 (16)0.0426 (18)0.0490 (18)−0.0001 (14)0.0256 (14)0.0123 (14)
C5A0.0425 (17)0.0315 (16)0.0520 (19)−0.0031 (13)0.0265 (15)0.0102 (14)
C6A0.0302 (14)0.0306 (15)0.0331 (15)0.0008 (11)0.0149 (12)0.0082 (12)
C7A0.0263 (13)0.0243 (13)0.0247 (13)−0.0020 (10)0.0092 (11)0.0019 (10)
C8A0.0277 (13)0.0202 (12)0.0259 (13)−0.0006 (10)0.0111 (11)0.0019 (10)
C9A0.0359 (15)0.0231 (13)0.0357 (15)0.0007 (11)0.0174 (13)0.0030 (11)
C10A0.0429 (17)0.0242 (14)0.0427 (17)0.0071 (12)0.0226 (14)−0.0007 (12)
C11A0.0321 (14)0.0343 (15)0.0339 (15)0.0000 (12)0.0182 (13)−0.0027 (12)
C12A0.0287 (14)0.0277 (14)0.0273 (14)−0.0035 (11)0.0117 (11)0.0006 (11)
C13A0.0288 (13)0.0202 (12)0.0246 (13)−0.0017 (10)0.0115 (11)0.0000 (10)
C14A0.0353 (16)0.0524 (19)0.0362 (16)−0.0049 (14)0.0199 (14)0.0054 (14)
C15A0.049 (2)0.059 (2)0.059 (2)−0.0151 (17)0.0297 (18)0.0116 (18)
O1B0.0528 (13)0.0209 (10)0.0370 (12)0.0008 (9)0.0139 (10)−0.0005 (8)
O2B0.0737 (17)0.0314 (12)0.0355 (12)0.0072 (11)0.0143 (12)0.0051 (9)
N1B0.0361 (13)0.0250 (12)0.0356 (13)0.0000 (10)0.0159 (11)−0.0009 (10)
N2B0.0370 (13)0.0203 (11)0.0390 (13)0.0024 (10)0.0233 (11)0.0035 (10)
C1B0.0365 (15)0.0277 (14)0.0379 (16)0.0032 (12)0.0200 (13)0.0030 (12)
C2B0.0485 (19)0.0346 (17)0.0410 (17)−0.0007 (14)0.0172 (15)−0.0021 (13)
C3B0.0463 (18)0.0474 (19)0.0372 (17)−0.0037 (15)0.0158 (15)−0.0010 (14)
C4B0.0397 (17)0.055 (2)0.0370 (17)0.0017 (15)0.0172 (14)0.0107 (15)
C5B0.0436 (17)0.0351 (16)0.0449 (18)0.0063 (13)0.0265 (15)0.0145 (13)
C6B0.0328 (14)0.0309 (14)0.0370 (15)−0.0007 (12)0.0228 (13)0.0043 (12)
C7B0.0326 (14)0.0255 (14)0.0380 (15)0.0012 (11)0.0234 (13)0.0011 (11)
C8B0.0314 (14)0.0243 (13)0.0384 (15)0.0001 (11)0.0237 (12)−0.0023 (11)
C9B0.0370 (15)0.0202 (13)0.0438 (16)0.0021 (11)0.0278 (14)0.0009 (11)
C10B0.0397 (16)0.0238 (14)0.0452 (17)−0.0052 (12)0.0282 (14)−0.0108 (12)
C11B0.0402 (16)0.0329 (15)0.0348 (15)0.0002 (12)0.0196 (13)−0.0061 (12)
C12B0.0462 (17)0.0288 (15)0.0373 (16)0.0029 (13)0.0225 (14)−0.0005 (12)
C13B0.0383 (15)0.0231 (13)0.0390 (16)−0.0022 (11)0.0230 (13)−0.0051 (11)
C14B0.071 (3)0.046 (2)0.0390 (19)0.0051 (18)0.0161 (18)0.0034 (16)
C15B0.067 (5)0.070 (5)0.044 (4)0.014 (4)0.008 (3)0.013 (3)
C15C0.062 (6)0.049 (5)0.068 (6)0.014 (4)0.024 (5)0.009 (4)
Geometric parameters (Å, °) top
O1A—C13A1.358 (3)N1B—C7B1.332 (3)
O1A—H1OA0.91 (4)N1B—C1B1.384 (4)
O2A—C12A1.374 (3)N2B—C7B1.356 (3)
O2A—C14A1.431 (3)N2B—C6B1.383 (4)
N1A—C7A1.330 (3)N2B—H1NB0.94 (4)
N1A—C1A1.388 (3)C1B—C2B1.396 (4)
N2A—C7A1.361 (3)C1B—C6B1.407 (4)
N2A—C6A1.376 (4)C2B—C3B1.381 (4)
N2A—H1NA0.82 (4)C2B—H2BA0.9300
C1A—C2A1.399 (4)C3B—C4B1.397 (5)
C1A—C6A1.404 (4)C3B—H3BA0.9300
C2A—C3A1.381 (4)C4B—C5B1.387 (5)
C2A—H2AA0.9300C4B—H4BA0.9300
C3A—C4A1.378 (4)C5B—C6B1.393 (4)
C3A—H3AA0.9300C5B—H5BA0.9300
C4A—C5A1.383 (4)C7B—C8B1.453 (4)
C4A—H4AA0.9300C8B—C13B1.396 (4)
C5A—C6A1.390 (4)C8B—C9B1.410 (4)
C5A—H5AA0.9300C9B—C10B1.374 (4)
C7A—C8A1.463 (4)C9B—H9BA0.9300
C8A—C9A1.400 (4)C10B—C11B1.400 (4)
C8A—C13A1.404 (3)C10B—H10B0.9300
C9A—C10A1.373 (4)C11B—C12B1.378 (4)
C9A—H9AA0.9300C11B—H11B0.9300
C10A—C11A1.400 (4)C12B—C13B1.399 (4)
C10A—H10A0.9300C14B—C15C1.4633 (10)
C11A—C12A1.373 (4)C14B—C15B1.464 (7)
C11A—H11A0.9300C14B—H14C0.9700
C12A—C13A1.403 (4)C14B—H14D0.9700
C14A—C15A1.519 (5)C14B—H14E0.9599
C14A—H14A0.9700C14B—H14F0.9600
C14A—H14B0.9700C15B—H14E0.7332
C15A—H15A0.9600C15B—H15D0.9600
C15A—H15B0.9600C15B—H15E0.9600
C15A—H15C0.9600C15B—H15F0.9600
O1B—C13B1.358 (3)C15C—H15G0.9600
O1B—H1OB0.97 (4)C15C—H15H0.9600
O2B—C12B1.370 (4)C15C—H15I0.9600
O2B—C14B1.441 (4)
C13A—O1A—H1OA98 (2)C3B—C2B—C1B118.0 (3)
C12A—O2A—C14A117.6 (2)C3B—C2B—H2BA121.0
C7A—N1A—C1A105.9 (2)C1B—C2B—H2BA121.0
C7A—N2A—C6A107.6 (2)C2B—C3B—C4B121.5 (3)
C7A—N2A—H1NA126 (2)C2B—C3B—H3BA119.3
C6A—N2A—H1NA126 (2)C4B—C3B—H3BA119.3
N1A—C1A—C2A130.9 (2)C5B—C4B—C3B121.7 (3)
N1A—C1A—C6A108.9 (2)C5B—C4B—H4BA119.1
C2A—C1A—C6A120.2 (3)C3B—C4B—H4BA119.1
C3A—C2A—C1A117.5 (3)C4B—C5B—C6B116.5 (3)
C3A—C2A—H2AA121.3C4B—C5B—H5BA121.8
C1A—C2A—H2AA121.3C6B—C5B—H5BA121.8
C4A—C3A—C2A121.9 (3)N2B—C6B—C5B132.4 (3)
C4A—C3A—H3AA119.0N2B—C6B—C1B105.2 (2)
C2A—C3A—H3AA119.0C5B—C6B—C1B122.4 (3)
C3A—C4A—C5A121.7 (3)N1B—C7B—N2B111.9 (2)
C3A—C4A—H4AA119.1N1B—C7B—C8B122.8 (2)
C5A—C4A—H4AA119.1N2B—C7B—C8B125.3 (2)
C4A—C5A—C6A117.1 (3)C13B—C8B—C9B118.6 (3)
C4A—C5A—H5AA121.5C13B—C8B—C7B118.8 (2)
C6A—C5A—H5AA121.5C9B—C8B—C7B122.7 (2)
N2A—C6A—C5A132.5 (3)C10B—C9B—C8B120.2 (3)
N2A—C6A—C1A105.8 (2)C10B—C9B—H9BA119.9
C5A—C6A—C1A121.6 (3)C8B—C9B—H9BA119.9
N1A—C7A—N2A111.8 (2)C9B—C10B—C11B121.0 (3)
N1A—C7A—C8A123.0 (2)C9B—C10B—H10B119.5
N2A—C7A—C8A125.2 (2)C11B—C10B—H10B119.5
C9A—C8A—C13A119.4 (2)C12B—C11B—C10B119.3 (3)
C9A—C8A—C7A122.6 (2)C12B—C11B—H11B120.3
C13A—C8A—C7A118.0 (2)C10B—C11B—H11B120.3
C10A—C9A—C8A120.2 (3)O2B—C12B—C11B125.7 (3)
C10A—C9A—H9AA119.9O2B—C12B—C13B114.1 (3)
C8A—C9A—H9AA119.9C11B—C12B—C13B120.2 (3)
C9A—C10A—C11A120.5 (3)O1B—C13B—C8B122.5 (3)
C9A—C10A—H10A119.8O1B—C13B—C12B116.8 (3)
C11A—C10A—H10A119.8C8B—C13B—C12B120.6 (3)
C12A—C11A—C10A120.2 (3)O2B—C14B—C15C108.0 (5)
C12A—C11A—H11A119.9O2B—C14B—C15B107.6 (4)
C10A—C11A—H11A119.9C15C—C14B—C15B88.1 (5)
C11A—C12A—O2A126.0 (2)O2B—C14B—H14C110.2
C11A—C12A—C13A120.0 (2)C15C—C14B—H14C129.3
O2A—C12A—C13A114.1 (2)C15B—C14B—H14C110.2
O1A—C13A—C12A117.0 (2)O2B—C14B—H14D110.2
O1A—C13A—C8A123.3 (2)C15B—C14B—H14D110.2
C12A—C13A—C8A119.8 (2)H14C—C14B—H14D108.5
O2A—C14A—C15A106.2 (3)O2B—C14B—H14E109.5
O2A—C14A—H14A110.5C15C—C14B—H14E111.1
C15A—C14A—H14A110.5H14C—C14B—H14E85.9
O2A—C14A—H14B110.5H14D—C14B—H14E129.1
C15A—C14A—H14B110.5O2B—C14B—H14F110.8
H14A—C14A—H14B108.7C15C—C14B—H14F109.1
C14A—C15A—H15A109.5C15B—C14B—H14F129.5
C14A—C15A—H15B109.5H14D—C14B—H14F85.8
H15A—C15A—H15B109.5H14E—C14B—H14F108.3
C14A—C15A—H15C109.5C14B—C15B—H15D109.5
H15A—C15A—H15C109.5H14E—C15B—H15D100.5
H15B—C15A—H15C109.5C14B—C15B—H15E109.5
C13B—O1B—H1OB106 (2)H14E—C15B—H15E141.2
C12B—O2B—C14B118.2 (3)C14B—C15B—H15F109.5
C7B—N1B—C1B105.8 (2)H14E—C15B—H15F81.8
C7B—N2B—C6B107.8 (2)C14B—C15C—H15G109.5
C7B—N2B—H1NB127 (2)C14B—C15C—H15H109.5
C6B—N2B—H1NB125 (2)H15G—C15C—H15H109.5
N1B—C1B—C2B130.9 (3)C14B—C15C—H15I109.5
N1B—C1B—C6B109.4 (3)H15G—C15C—H15I109.5
C2B—C1B—C6B119.8 (3)H15H—C15C—H15I109.5
C7A—N1A—C1A—C2A−177.4 (3)C7B—N1B—C1B—C6B−1.1 (3)
C7A—N1A—C1A—C6A0.6 (3)N1B—C1B—C2B—C3B179.8 (3)
N1A—C1A—C2A—C3A178.1 (3)C6B—C1B—C2B—C3B−0.6 (5)
C6A—C1A—C2A—C3A0.3 (4)C1B—C2B—C3B—C4B−1.2 (5)
C1A—C2A—C3A—C4A−0.1 (5)C2B—C3B—C4B—C5B1.7 (5)
C2A—C3A—C4A—C5A−0.2 (5)C3B—C4B—C5B—C6B−0.1 (5)
C3A—C4A—C5A—C6A0.2 (5)C7B—N2B—C6B—C5B178.4 (3)
C7A—N2A—C6A—C5A177.6 (3)C7B—N2B—C6B—C1B−0.6 (3)
C7A—N2A—C6A—C1A−1.1 (3)C4B—C5B—C6B—N2B179.3 (3)
C4A—C5A—C6A—N2A−178.5 (3)C4B—C5B—C6B—C1B−1.8 (4)
C4A—C5A—C6A—C1A0.0 (4)N1B—C1B—C6B—N2B1.1 (3)
N1A—C1A—C6A—N2A0.3 (3)C2B—C1B—C6B—N2B−178.6 (3)
C2A—C1A—C6A—N2A178.6 (2)N1B—C1B—C6B—C5B−178.1 (2)
N1A—C1A—C6A—C5A−178.6 (3)C2B—C1B—C6B—C5B2.2 (4)
C2A—C1A—C6A—C5A−0.3 (4)C1B—N1B—C7B—N2B0.7 (3)
C1A—N1A—C7A—N2A−1.3 (3)C1B—N1B—C7B—C8B−179.1 (2)
C1A—N1A—C7A—C8A179.1 (2)C6B—N2B—C7B—N1B0.0 (3)
C6A—N2A—C7A—N1A1.5 (3)C6B—N2B—C7B—C8B179.7 (2)
C6A—N2A—C7A—C8A−178.9 (2)N1B—C7B—C8B—C13B−11.6 (4)
N1A—C7A—C8A—C9A179.5 (3)N2B—C7B—C8B—C13B168.7 (3)
N2A—C7A—C8A—C9A0.0 (4)N1B—C7B—C8B—C9B168.0 (3)
N1A—C7A—C8A—C13A−1.2 (4)N2B—C7B—C8B—C9B−11.8 (4)
N2A—C7A—C8A—C13A179.3 (2)C13B—C8B—C9B—C10B0.4 (4)
C13A—C8A—C9A—C10A−0.7 (4)C7B—C8B—C9B—C10B−179.2 (2)
C7A—C8A—C9A—C10A178.5 (3)C8B—C9B—C10B—C11B−0.9 (4)
C8A—C9A—C10A—C11A0.9 (4)C9B—C10B—C11B—C12B−0.4 (4)
C9A—C10A—C11A—C12A−0.2 (4)C14B—O2B—C12B—C11B4.6 (5)
C10A—C11A—C12A—O2A179.4 (3)C14B—O2B—C12B—C13B−175.3 (3)
C10A—C11A—C12A—C13A−0.6 (4)C10B—C11B—C12B—O2B−177.9 (3)
C14A—O2A—C12A—C11A−6.6 (4)C10B—C11B—C12B—C13B2.1 (4)
C14A—O2A—C12A—C13A173.4 (2)C9B—C8B—C13B—O1B−178.5 (3)
C11A—C12A—C13A—O1A−179.0 (2)C7B—C8B—C13B—O1B1.1 (4)
O2A—C12A—C13A—O1A1.0 (3)C9B—C8B—C13B—C12B1.3 (4)
C11A—C12A—C13A—C8A0.7 (4)C7B—C8B—C13B—C12B−179.1 (3)
O2A—C12A—C13A—C8A−179.3 (2)O2B—C12B—C13B—O1B−2.8 (4)
C9A—C8A—C13A—O1A179.7 (2)C11B—C12B—C13B—O1B177.3 (3)
C7A—C8A—C13A—O1A0.4 (4)O2B—C12B—C13B—C8B177.4 (3)
C9A—C8A—C13A—C12A0.0 (4)C11B—C12B—C13B—C8B−2.5 (4)
C7A—C8A—C13A—C12A−179.4 (2)C12B—O2B—C14B—C15C−87.0 (5)
C12A—O2A—C14A—C15A−177.4 (2)C12B—O2B—C14B—C15B179.2 (4)
C7B—N1B—C1B—C2B178.6 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···N1A0.91 (4)1.67 (4)2.557 (4)164 (4)
N2A—H1NA···O1B0.81 (4)2.14 (4)2.865 (3)149 (3)
N2A—H1NA···O2B0.81 (4)2.57 (4)3.199 (3)136 (3)
O1B—H1OB···N1B0.97 (4)1.67 (4)2.567 (3)151 (3)
N2B—H1NB···O1Ai0.94 (4)1.95 (4)2.877 (3)167 (4)
N2B—H1NB···O2Ai0.94 (4)2.55 (4)3.136 (3)121 (3)
C4A—H4AA···Cg1ii0.932.803.590 (4)143
C14B—H14C···Cg2iii0.972.843.721 (5)152
C15B—H15D···Cg3iv0.962.763.715 (8)176
Symmetry codes: (i) −x, y+1, −z+1/2; (ii) x, −y−1, z−1/2; (iii) −x, y, −z+1/2; (iv) −x+1/2, −y+1/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···N1A0.91 (4)1.67 (4)2.557 (4)164 (4)
N2A—H1NA···O1B0.81 (4)2.14 (4)2.865 (3)149 (3)
N2A—H1NA···O2B0.81 (4)2.57 (4)3.199 (3)136 (3)
O1B—H1OB···N1B0.97 (4)1.67 (4)2.567 (3)151 (3)
N2B—H1NB···O1Ai0.94 (4)1.95 (4)2.877 (3)167 (4)
N2B—H1NB···O2Ai0.94 (4)2.55 (4)3.136 (3)121 (3)
C4A—H4AA···Cg1ii0.932.803.590 (4)143
C14B—H14C···Cg2iii0.972.843.721 (5)152
C15B—H15D···Cg3iv0.962.763.715 (8)176
Symmetry codes: (i) −x, y+1, −z+1/2; (ii) x, −y−1, z−1/2; (iii) −x, y, −z+1/2; (iv) −x+1/2, −y+1/2, −z+1.
Acknowledgements top

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. YCS thanks Universiti Sains Malaysia for a studentship award. HK and AJ thank PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

references
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