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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 9| September 2011| Pages o2243-o2244
doi:10.1107/S1600536811030583

2-(5,6-Di­hydro­benzimidazo[1,2-c]quinazolin-6-yl)phenol

Naser Eltaher Eltayeb,a Siang Guan Teoh,b Ching Kheng Quahc‡ and Hoong-Kun Func*§

aDepartment of Chemistry, Faculty of Pure and Applied Sciences, International University of Africa, Sudan, and, School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 20 July 2011; accepted 29 July 2011; online 6 August 2011)

The asymmetric unit of the title compound, C20H15N3O, contains two independent mol­ecules, each of which is disordered over two sets of sites corresponding to a rotation of approximately 180° of the dihydro­benzimidazoquinazoline moiety, with refined site occupancies of 0.7479 (13) and 0.2521 (12) for both mol­ecules. The pyrimidine rings are in sofa conformations. In one mol­ecule, the hy­droxy-substituted benzene ring forms dihedral angles of 83.9 (3) and 82.4 (4)° for the major and minor components, respectively, with the mean plane of the benzimidazole ring system. The corres­ponding dihedral angles in the other mol­ecule are 88.31 (14) and 85.8 (6)°. In the crystal, mol­ecules are linked via inter­molecular O—H⋯N and N—H.·O hydrogen bonds into chains along [100].

Related literature

For general background to and the biological activity of benzimidazole compounds, see: Minoura et al. (2004[Minoura, H., Takeshita, S., Ita, M., Hirosumi, J., Mabuchi, M., Kawamura, I., Nakajima, S., Nakayama, O., Kayakiri, H., Oku, T., Ohkubo-Suzuki, A., Fukagawa, M., Kojo, H., Hanioka, K., Yamasaki, N., Imoto, T., Kobayashi, Y. & Mutoh, S. (2004). Eur. J. Pharmacol. 494, 273-281.]); Pawar et al. (2004[Pawar, N. S., Dalal, D. S., Shimpi, S. R. & Mahulikar, P. P. (2004). Eur. J. Pharm. Sci. 21, 115-118.]); Tomei et al. (2003[Tomei, L., Altamura, S., Bartholomew, L., Biroccio, A., Ceccacci, A., Pacini, L., Narjes, F., Gennari, N., Bisbocci, M., Incitti, I., Orsatti, L., Harper, S., Stansfield, I., Rowley, M., De Francesco, R. & Migliaccio, G. (2003). J. Virol. 77, 13225-13231.]); Barreca et al. (2003)[Barreca, M. L., Chimirri, A., De Clercq, E., De Luca, L., Monforte, A.-M., Monforte, P., Rao, A. & Zappalà, M. (2003). Farmaco, 58, 259-263.]; Demirayak et al. (2002[Demirayak, S., Abu Mohsen, U. & Cagri Karaburun, A. (2002). Eur. J. Med. Chem. 37, 255-260.]). For the synthesis, see: Eltayeb et al. (2011[Eltayeb, N. E., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2011). Acta Cryst. E67, o1721-o1722.]). For related structures, see: Eltayeb et al. (2007a[Eltayeb, N. E., Teoh, S. G., Chantrapromma, S. & Fun, H.-K. (2007a). Acta Cryst. E63, o4141-o4142.],b[Eltayeb, N. E., Teoh, S. G., Teh, J. B.-J., Fun, H.-K. & Ibrahim, K. (2007b). Acta Cryst. E63, o465-o467.],c[Eltayeb, N. E., Teoh, S. G., Teh, J. B.-J., Fun, H.-K. & Ibrahim, K. (2007c). Acta Cryst. E63, o300-o302.], 2009[Eltayeb, N. E., Teoh, S. G., Quah, C. K., Fun, H.-K. & Adnan, R. (2009). Acta Cryst. E65, o1613-o1614.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C20H15N3O

  • Mr = 313.35

  • Monoclinic, P 21 /c

  • a = 17.1513 (10) Å

  • b = 19.1160 (11) Å

  • c = 9.2630 (5) Å

  • β = 97.590 (1)°

  • V = 3010.4 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 297 K

  • 0.30 × 0.28 × 0.25 mm
Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.974, Tmax = 0.978

  • 40861 measured reflections

  • 11057 independent reflections

  • 8231 reflections with I > 2σ(I)

  • Rint = 0.047
Refinement

  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.158

  • S = 1.05

  • 11057 reflections

  • 625 parameters

  • 144 restraints

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1A—H1OA⋯N1Bi 0.98 1.69 2.641 (3) 162
N3A—H3AB⋯O1Aii 0.86 2.50 3.241 (3) 144
O1B—H1OB⋯N1Aiii 0.97 1.79 2.686 (4) 151
N3B—H3BB⋯O1Biv 0.86 2.15 2.974 (4) 160
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z+2; (iii) -x+2, -y+1, -z+1; (iv) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT; data reduction: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811030583/lh5291sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811030583/lh5291Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811030583/lh5291Isup3.cml

checkCIF report


Comment top

The synthesis of benzimidazoles has received much attention owing to the varied biological activity such as antidiabetic (Minoura et al., 2004), antimicrobial, antifungal (Pawar et al., 2004), antiviral (Tomei et al., 2003), antiHIV (Barreca et al., 2003) and anticancer (Demirayak et al., 2002) properties exhibited by a number of derivatives of these compounds. Previously we reported the crystal structures of 4-allyl-2-[1-(5-allyl-2-hydroxy-3-methoxybenzyl) -1H-benzimidazol-2-yl]-6-methoxyphenol (Eltayeb et al., 2007a), 2-(2-methoxynaphthalen-1-yl)-1-[(2-methoxynaphthalen-1-yl)methyl] -1H-benzimidazole (Eltayeb et al., 2007b), 2-(benzimidazol-2-yl) -6-methoxyphenol (Eltayeb et al., 2007c) and 2-methoxy-6-(6-methyl -1H-benzimidazol-2-yl)phenol (Eltayeb et al., 2009). Considering the biological importance of the included benzimidazole ring, we describe in this paper the single crystal X-ray diffraction study of 2-(5,6- dihydrobenzimidazo[1,2-c]quinazolin-6-yl)phenol.

The asymmetric unit contains two independent molecules (Fig. 1), A and B. In each molecule, the benzimidazole fused ring system is disordered over two sets of sites with refined site occupancies of 0.748 (1) : 0.252 (1), suggesting 180° rotational disorder for the benzimidazole fused ring system. The conformations for pyrimidine rings are close to a sofa conformation (Cremer & Pople, 1975), puckering parameters Q = 0.330 (2) Å, Θ = 61.9 (3)° and ϕ = 277.5 (4)° (major component of molecule A), Q = 0.305 (12) Å, Θ = 120.6 (19)° and ϕ = 103.9 (19)° (minor component of molecule A), Q = 0.343 (3) Å, Θ = 60.4 (4)° and ϕ = 285.8 (4)° (major component of molecule B) and Q = 0.331 (11) Å, Θ = 119.3 (14)° and ϕ = 104.7 (14)° (minor component of molecule B). Bond lengths (Allen et al., 1987) and angles are within normal ranges. In molecule A (Fig. 2), the hydroxyphenyl ring (C15-C20) is almost perpendicular to the mean plane of benzimidazole ring (N1/N2/C1-C7) with the dihedral angles of 83.9 (3) and 82.4 (4)° for major and minor components, respectively. The corresponding dihedral angles for molecule B are 88.31 (14) and 85.8 (6)°.

In the crystal structure, Fig. 3, the molecules are linked via intermolecular O1A–H10A···N1Bi, N3A–H3AB···O1Aii, O1B–H10B···N1Aiii and N3B–H3BB..O1Biv hydrogen bonds (Table 1) into infinite one-dimensional chains along [100].

Related literature top

For general background to and the biological activity of benzimidazole compounds, see: Minoura et al. (2004); Pawar et al. (2004); Tomei et al. (2003); Barreca et al. (2003); Demirayak et al. (2002). For the sythesis, see: Eltayeb et al. (2011). For related structures, see: Eltayeb et al. (2007a,b,c, 2009). For bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975).

Experimental top

The title compound was synthesized using Taha-Teoh's method (Eltayeb et al., 2011). To a solution of 2-(2-aminophenyl)-1H-benzimidazole (0.209 g, 1.0 mmol) in ethanol (30 mL) was added 2-hydroxybenzaldehyde (0.1 mL, 1.0 mmol). The color of the resulting solution is pale-yellow. Then on adding zinc chloride (0.136 g, 1.0 mmol), the color of the solution became golden-yellow. The mixture was refluxed with stirring for 3 h. Crystals suitable for XRD were formed after several days of slow evaporation of ethanol at room temperature.

Refinement top

The title compound is disordered over two positions with refined site-occupancies of 0.748 (1) : 0.252 (1). All minor disordered components were refined isotropically. The O-bound hydrogen atoms were located from difference Fourier map and refined as riding on their parent atom, with Uiso(H) = 1.2 Ueq(O). The rest of the hydrogen atoms were positioned geomatrically [C–H = 0.93 - 0.98 Å; N–H = 0.86 Å] and refined using a riding model, with Uiso(H) = 1.2 Ueq(C, N). The highest residual electron density peak and the deepest hole are located at 0.68 Å and 0.12 Å, respectively, from H3AB. The same Uij parameters were used for atom pair C16Y/C12Y.

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 showing 50% probability displacement ellipsoids for non-H atoms. All components are shown.
[Figure 2] Fig. 2. The molecular structure of the major component of molecule A showing 50% probability displacement ellipsoids for non-H atoms.
[Figure 3] Fig. 3. Part of the crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity. Only the major disorder component is shown.
2-(5,6-Dihydrobenzimidazo[1,2-c]quinazolin-6-yl)phenol top
Crystal data top
C20H15N3OF(000) = 1312
Mr = 313.35Dx = 1.383 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9430 reflections
a = 17.1513 (10) Åθ = 2.4–32.7°
b = 19.1160 (11) ŵ = 0.09 mm−1
c = 9.2630 (5) ÅT = 297 K
β = 97.590 (1)°Block, yellow
V = 3010.4 (3) Å30.30 × 0.28 × 0.25 mm
Z = 8
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer		11057 independent reflections
Radiation source: fine-focus sealed tube8231 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ϕ and ω scansθmax = 32.8°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −26→26
Tmin = 0.974, Tmax = 0.978k = −29→29
40861 measured reflectionsl = −12→14
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0604P)2 + 1.3534P]
where P = (Fo2 + 2Fc2)/3
11057 reflections(Δ/σ)max = 0.001
625 parametersΔρmax = 0.44 e Å−3
144 restraintsΔρmin = −0.42 e Å−3
Crystal data top
C20H15N3OV = 3010.4 (3) Å3
Mr = 313.35Z = 8
Monoclinic, P21/cMo Kα radiation
a = 17.1513 (10) ŵ = 0.09 mm−1
b = 19.1160 (11) ÅT = 297 K
c = 9.2630 (5) Å0.30 × 0.28 × 0.25 mm
β = 97.590 (1)°
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer		11057 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		8231 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.978Rint = 0.047
40861 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.058144 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 1.05Δρmax = 0.44 e Å−3
11057 reflectionsΔρmin = −0.42 e Å−3
625 parameters
Special details top

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)
O1A0.47310 (12)0.61154 (16)0.9445 (3)0.0161 (5)0.7479 (13)
H1OA0.41590.60510.92530.019*0.7479 (13)
N1A0.82502 (7)0.56968 (7)0.82493 (16)0.0190 (3)0.7479 (13)
N2A0.71433 (7)0.59508 (7)0.91751 (15)0.0155 (2)0.7479 (13)
N3A0.60604 (7)0.51973 (7)0.90775 (16)0.0166 (3)0.7479 (13)
H3AB0.57450.50140.96200.020*0.7479 (13)
C1A0.83777 (10)0.62752 (8)0.91544 (19)0.0184 (3)0.7479 (13)
C2A0.90681 (10)0.66651 (10)0.9555 (2)0.0250 (4)0.7479 (13)
H2AA0.95330.65600.91850.030*0.7479 (13)
C3A0.90283 (12)0.72153 (12)1.0530 (3)0.0306 (5)0.7479 (13)
H3AA0.94780.74781.08200.037*0.7479 (13)
C4A0.83290 (15)0.73839 (12)1.1087 (3)0.0346 (5)0.7479 (13)
H4AA0.83240.77551.17350.042*0.7479 (13)
C5A0.76429 (11)0.70022 (11)1.0683 (3)0.0296 (4)0.7479 (13)
H5AA0.71750.71141.10360.036*0.7479 (13)
C6A0.76874 (9)0.64467 (9)0.9730 (2)0.0184 (3)0.7479 (13)
C7A0.75068 (11)0.55190 (12)0.8291 (2)0.0153 (3)0.7479 (13)
C8A0.70730 (9)0.49398 (8)0.75729 (18)0.0154 (3)0.7479 (13)
C9A0.63282 (9)0.47982 (8)0.79902 (18)0.0151 (3)0.7479 (13)
C10A0.59061 (10)0.42188 (10)0.7374 (2)0.0208 (3)0.7479 (13)
H10A0.54130.41170.76320.025*0.7479 (13)
C11A0.62240 (14)0.37973 (11)0.6380 (2)0.0261 (4)0.7479 (13)
H11A0.59400.34150.59760.031*0.7479 (13)
C12A0.69640 (14)0.39393 (11)0.5979 (2)0.0269 (4)0.7479 (13)
H12A0.71730.36530.53150.032*0.7479 (13)
C13A0.73847 (10)0.45117 (10)0.6579 (2)0.0212 (3)0.7479 (13)
H13A0.78780.46100.63150.025*0.7479 (13)
C14A0.63058 (13)0.59199 (16)0.9310 (3)0.0124 (6)0.7479 (13)
H14A0.62370.60511.03080.015*0.7479 (13)
C15A0.58296 (14)0.64264 (17)0.8268 (3)0.0125 (7)0.7479 (13)
C16A0.61480 (14)0.68116 (17)0.7214 (3)0.0201 (6)0.7479 (13)
H16A0.66740.67530.70920.024*0.7479 (13)
C17A0.5679 (3)0.7286 (4)0.6337 (8)0.0340 (15)0.7479 (13)
H17A0.58980.75510.56500.041*0.7479 (13)
C18A0.48936 (16)0.73634 (19)0.6488 (4)0.0233 (8)0.7479 (13)
H18A0.45830.76730.58890.028*0.7479 (13)
C19A0.45662 (18)0.6981 (2)0.7532 (5)0.0178 (9)0.7479 (13)
H19A0.40390.70410.76430.021*0.7479 (13)
C20A0.50286 (14)0.65047 (16)0.8415 (3)0.0117 (6)0.7479 (13)
O1B1.03721 (19)0.4897 (2)0.2130 (4)0.0231 (6)0.7479 (13)
H1OB1.09340.47970.22330.028*0.7479 (13)
N1B0.67513 (8)0.41530 (9)0.15645 (18)0.0253 (3)0.7479 (13)
N2B0.79070 (8)0.47098 (8)0.16595 (18)0.0237 (3)0.7479 (13)
N3B0.88892 (9)0.44281 (9)0.02448 (18)0.0261 (3)0.7479 (13)
H3BB0.92050.4619−0.02860.031*0.7479 (13)
C1B0.67384 (10)0.47560 (10)0.2429 (2)0.0243 (3)0.7479 (13)
C2B0.61365 (12)0.50263 (11)0.3142 (2)0.0288 (4)0.7479 (13)
H2BA0.56550.47990.31090.035*0.7479 (13)
C3B0.62839 (19)0.5640 (2)0.3893 (5)0.0256 (7)0.7479 (13)
H3BA0.58870.58310.43620.031*0.7479 (13)
C4B0.70066 (18)0.59922 (17)0.3987 (4)0.0341 (6)0.7479 (13)
H4BA0.70840.64040.45220.041*0.7479 (13)
C5B0.76129 (11)0.57226 (12)0.3270 (3)0.0302 (4)0.7479 (13)
H5BA0.80960.59470.33100.036*0.7479 (13)
C6B0.74580 (12)0.51085 (10)0.2504 (2)0.0233 (3)0.7479 (13)
C7B0.74581 (9)0.41479 (10)0.1156 (2)0.0216 (3)0.7479 (13)
C8B0.77894 (10)0.36412 (10)0.0230 (2)0.0216 (3)0.7479 (13)
C9B0.85229 (10)0.38073 (10)−0.0204 (2)0.0227 (3)0.7479 (13)
C10B0.88395 (10)0.33569 (11)−0.1166 (2)0.0266 (4)0.7479 (13)
H10B0.93250.3457−0.14610.032*0.7479 (13)
C11B0.84375 (12)0.27688 (12)−0.1674 (3)0.0265 (4)0.7479 (13)
H11B0.86570.2480−0.23210.032*0.7479 (13)
C12B0.7707 (2)0.25862 (17)−0.1257 (4)0.0244 (6)0.7479 (13)
H12B0.74460.2182−0.16060.029*0.7479 (13)
C13B0.73862 (11)0.30330 (12)−0.0298 (3)0.0262 (4)0.7479 (13)
H13B0.69010.2927−0.00050.031*0.7479 (13)
C14B0.87512 (14)0.4770 (2)0.1610 (5)0.0165 (8)0.7479 (13)
H14B0.88930.52650.15700.020*0.7479 (13)
C15B0.92214 (18)0.4436 (2)0.2945 (4)0.0144 (10)0.7479 (13)
C16B0.88769 (15)0.40564 (16)0.3972 (3)0.0179 (5)0.7479 (13)
H16B0.83330.40090.38680.022*0.7479 (13)
C17B0.93327 (19)0.3747 (2)0.5154 (4)0.0224 (8)0.7479 (13)
H17B0.90940.34920.58300.027*0.7479 (13)
C18B1.0145 (2)0.3818 (2)0.5324 (5)0.0211 (7)0.7479 (13)
H18B1.04480.36170.61240.025*0.7479 (13)
C19B1.0507 (3)0.4187 (4)0.4312 (6)0.0222 (9)0.7479 (13)
H19B1.10520.42340.44220.027*0.7479 (13)
C20B1.0042 (3)0.4486 (3)0.3125 (6)0.0208 (9)0.7479 (13)
O1X0.4731 (8)0.6132 (8)0.9421 (16)0.055 (4)*0.2521 (13)
H1OX0.42540.60710.93010.066*0.2521 (13)
N1X0.7962 (3)0.5228 (3)0.7655 (6)0.0338 (11)*0.2521 (13)
N2X0.6853 (3)0.5492 (3)0.8586 (6)0.0356 (12)*0.2521 (13)
N3X0.6784 (3)0.6299 (3)1.0464 (7)0.0429 (14)*0.2521 (13)
H3XB0.66020.63611.12760.051*0.2521 (13)
C1X0.7358 (3)0.4754 (3)0.7172 (7)0.0264 (11)*0.2521 (13)
C2X0.7366 (4)0.4182 (4)0.6289 (8)0.0351 (14)*0.2521 (13)
H2XA0.78240.40570.59140.042*0.2521 (13)
C3X0.6704 (5)0.3800 (4)0.5966 (10)0.0367 (19)*0.2521 (13)
H3XA0.67030.34250.53270.044*0.2521 (13)
C4X0.6027 (5)0.3954 (4)0.6564 (10)0.0344 (19)*0.2521 (13)
H4XA0.55870.36690.63600.041*0.2521 (13)
C5X0.5998 (4)0.4525 (4)0.7459 (8)0.0331 (14)*0.2521 (13)
H5XA0.55450.46400.78560.040*0.2521 (13)
C6X0.6674 (4)0.4919 (3)0.7740 (7)0.0255 (10)*0.2521 (13)
C7X0.7623 (5)0.5673 (4)0.8464 (11)0.034 (3)*0.2521 (13)
C8X0.7975 (4)0.6267 (3)0.9330 (7)0.0300 (12)*0.2521 (13)
C9X0.7530 (4)0.6565 (4)1.0300 (8)0.0351 (14)*0.2521 (13)
C10X0.7850 (5)0.7112 (4)1.1162 (10)0.0420 (19)*0.2521 (13)
H10C0.75570.73281.18100.050*0.2521 (13)
C11X0.8593 (6)0.7332 (5)1.1061 (11)0.045 (3)*0.2521 (13)
H11C0.88040.76881.16750.054*0.2521 (13)
C12X0.9049 (5)0.7050 (5)1.0090 (9)0.035 (2)*0.2521 (13)
H12C0.95480.72231.00080.042*0.2521 (13)
C13X0.8731 (5)0.6502 (4)0.9245 (8)0.0334 (13)*0.2521 (13)
H13C0.90290.62850.86060.040*0.2521 (13)
C14X0.6312 (8)0.5922 (9)0.9299 (16)0.049 (5)*0.2521 (13)
H14C0.59580.56080.97400.058*0.2521 (13)
C15X0.5812 (8)0.6416 (9)0.8288 (18)0.044 (5)*0.2521 (13)
C16X0.6105 (10)0.6770 (9)0.7192 (19)0.065 (6)*0.2521 (13)
H16C0.66340.67040.71030.079*0.2521 (13)
C17X0.5687 (11)0.7214 (11)0.621 (2)0.028 (3)*0.2521 (13)
H17C0.59010.74100.54360.033*0.2521 (13)
C18X0.4932 (10)0.7351 (11)0.647 (2)0.063 (6)*0.2521 (13)
H18C0.46460.76950.59190.076*0.2521 (13)
C19X0.4586 (10)0.6994 (11)0.750 (2)0.046 (6)*0.2521 (13)
H19C0.40610.70720.76020.055*0.2521 (13)
C20X0.5018 (8)0.6524 (10)0.838 (2)0.048 (5)*0.2521 (13)
O1Y1.0330 (7)0.4857 (7)0.1895 (12)0.024 (2)*0.2521 (13)
H1OY1.08400.47850.20020.028*0.2521 (13)
N1Y0.6910 (2)0.38802 (19)0.0948 (4)0.0128 (7)*0.2521 (13)
N2Y0.8087 (2)0.43856 (19)0.1044 (4)0.0132 (7)*0.2521 (13)
N3Y0.8417 (2)0.5488 (2)0.2063 (4)0.0174 (7)*0.2521 (13)
H3YB0.86550.58720.19070.021*0.2521 (13)
C1Y0.7373 (2)0.3489 (2)0.0136 (5)0.0116 (7)*0.2521 (13)
C2Y0.7211 (4)0.2875 (3)−0.0681 (7)0.0241 (14)*0.2521 (13)
H2YA0.67290.2645−0.07500.029*0.2521 (13)
C3Y0.7835 (6)0.2639 (6)−0.1384 (14)0.025 (3)*0.2521 (13)
H3YA0.77480.2245−0.19740.030*0.2521 (13)
C4Y0.8562 (4)0.2940 (3)−0.1270 (7)0.0218 (13)*0.2521 (13)
H4YA0.89540.2732−0.17270.026*0.2521 (13)
C5Y0.8719 (3)0.3535 (3)−0.0503 (6)0.0152 (8)*0.2521 (13)
H5YA0.92060.3754−0.04480.018*0.2521 (13)
C6Y0.8125 (3)0.3803 (2)0.0192 (5)0.0105 (7)*0.2521 (13)
C7Y0.7352 (3)0.4417 (2)0.1501 (5)0.0138 (8)*0.2521 (13)
C8Y0.7164 (3)0.4979 (2)0.2431 (5)0.0131 (9)*0.2521 (13)
C9Y0.7740 (3)0.5507 (3)0.2677 (6)0.0195 (9)*0.2521 (13)
C10Y0.7561 (3)0.6108 (3)0.3521 (6)0.0258 (10)*0.2521 (13)
H10D0.79210.64720.36980.031*0.2521 (13)
C11Y0.6862 (6)0.6133 (5)0.4052 (14)0.036 (3)*0.2521 (13)
H11D0.67450.65290.45650.043*0.2521 (13)
C12Y0.6304 (11)0.5587 (9)0.386 (3)0.056 (4)*0.2521 (13)
H12D0.58450.56030.42970.067*0.2521 (13)
C13Y0.6468 (3)0.5023 (3)0.3001 (6)0.0192 (9)*0.2521 (13)
H13D0.60970.46680.28080.023*0.2521 (13)
C14Y0.8749 (8)0.4810 (7)0.166 (2)0.041 (5)*0.2521 (13)
H14D0.90780.49000.08920.050*0.2521 (13)
C15Y0.9251 (8)0.4442 (10)0.2900 (19)0.036 (6)*0.2521 (13)
C16Y0.8933 (9)0.4054 (9)0.3928 (19)0.056 (4)*0.2521 (13)
H16D0.83920.39850.38130.067*0.2521 (13)
C17Y0.9389 (10)0.3760 (11)0.514 (2)0.057 (6)*0.2521 (13)
H17D0.91710.35220.58620.069*0.2521 (13)
C18Y1.0187 (10)0.3851 (11)0.517 (2)0.046 (5)*0.2521 (13)
H18D1.05240.36270.58950.055*0.2521 (13)
C19Y1.0504 (10)0.4253 (12)0.419 (2)0.026 (4)*0.2521 (13)
H19D1.10470.43160.43040.031*0.2521 (13)
C20Y1.0060 (7)0.4567 (8)0.3046 (14)0.0095 (19)*0.2521 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0074 (5)0.0250 (8)0.0163 (7)0.0011 (4)0.0035 (3)0.0049 (5)
N1A0.0115 (5)0.0228 (6)0.0231 (7)0.0008 (4)0.0033 (4)0.0029 (6)
N2A0.0098 (5)0.0170 (5)0.0197 (6)0.0012 (4)0.0019 (4)−0.0012 (5)
N3A0.0134 (5)0.0164 (5)0.0212 (7)−0.0001 (4)0.0070 (4)0.0019 (5)
C1A0.0105 (6)0.0198 (7)0.0243 (8)−0.0009 (5)0.0008 (5)0.0052 (6)
C2A0.0134 (7)0.0249 (8)0.0350 (10)−0.0046 (6)−0.0030 (6)0.0057 (8)
C3A0.0214 (9)0.0263 (10)0.0410 (13)−0.0029 (7)−0.0069 (8)−0.0022 (10)
C4A0.0244 (10)0.0264 (10)0.0504 (15)0.0004 (8)−0.0053 (9)−0.0125 (9)
C5A0.0179 (7)0.0259 (9)0.0428 (12)0.0018 (6)−0.0037 (8)−0.0117 (9)
C6A0.0130 (6)0.0198 (7)0.0220 (8)0.0015 (5)0.0005 (6)−0.0020 (6)
C7A0.0113 (6)0.0175 (8)0.0176 (8)0.0030 (7)0.0040 (6)0.0033 (7)
C8A0.0118 (6)0.0172 (6)0.0179 (7)0.0027 (5)0.0047 (5)0.0005 (6)
C9A0.0128 (6)0.0154 (6)0.0175 (7)0.0001 (5)0.0032 (5)0.0032 (6)
C10A0.0199 (7)0.0184 (8)0.0239 (9)−0.0046 (6)0.0021 (6)0.0003 (7)
C11A0.0342 (10)0.0186 (8)0.0261 (10)−0.0038 (8)0.0063 (8)−0.0036 (7)
C12A0.0318 (10)0.0218 (8)0.0287 (10)0.0001 (8)0.0100 (8)−0.0042 (7)
C13A0.0229 (7)0.0196 (8)0.0223 (8)0.0020 (6)0.0075 (6)−0.0037 (7)
C14A0.0073 (7)0.0168 (9)0.0134 (9)0.0026 (4)0.0027 (4)0.0008 (5)
C15A0.0076 (7)0.0157 (9)0.0141 (10)0.0018 (4)0.0012 (4)0.0005 (5)
C16A0.0084 (6)0.0285 (10)0.0235 (10)0.0003 (5)0.0031 (5)0.0113 (7)
C17A0.0188 (11)0.040 (3)0.043 (3)−0.0027 (11)0.0015 (10)0.024 (2)
C18A0.0134 (7)0.0226 (10)0.0319 (13)0.0004 (5)−0.0042 (6)0.0144 (8)
C19A0.0090 (8)0.0189 (11)0.0244 (13)0.0020 (5)−0.0017 (5)0.0021 (6)
C20A0.0090 (7)0.0133 (8)0.0127 (9)0.0005 (4)0.0006 (4)−0.0006 (5)
O1B0.0110 (7)0.0381 (13)0.0213 (12)0.0031 (6)0.0060 (8)0.0082 (11)
N1B0.0152 (6)0.0329 (8)0.0274 (8)−0.0009 (5)0.0016 (5)0.0018 (7)
N2B0.0157 (6)0.0257 (7)0.0298 (8)0.0000 (5)0.0032 (5)0.0058 (6)
N3B0.0201 (6)0.0335 (8)0.0257 (8)−0.0034 (5)0.0070 (5)0.0063 (7)
C1B0.0165 (7)0.0318 (9)0.0246 (9)0.0031 (6)0.0022 (6)0.0032 (7)
C2B0.0180 (8)0.0399 (11)0.0288 (10)0.0018 (7)0.0036 (7)−0.0006 (8)
C3B0.0170 (8)0.0360 (12)0.0236 (10)0.0059 (7)0.0023 (6)−0.0044 (8)
C4B0.0307 (12)0.0370 (14)0.0336 (13)−0.0007 (11)0.0004 (10)−0.0056 (11)
C5B0.0219 (8)0.0321 (10)0.0360 (11)−0.0007 (7)0.0013 (7)0.0034 (9)
C6B0.0176 (8)0.0260 (8)0.0261 (9)0.0010 (7)0.0025 (6)0.0043 (7)
C7B0.0149 (6)0.0263 (8)0.0230 (8)−0.0002 (6)0.0002 (6)0.0066 (7)
C8B0.0169 (8)0.0257 (8)0.0224 (8)0.0021 (6)0.0027 (6)0.0057 (7)
C9B0.0175 (7)0.0288 (9)0.0216 (8)0.0021 (6)0.0024 (6)0.0056 (7)
C10B0.0192 (7)0.0368 (10)0.0238 (9)0.0016 (7)0.0025 (6)0.0036 (8)
C11B0.0220 (8)0.0311 (10)0.0263 (10)0.0047 (7)0.0029 (7)0.0019 (9)
C12B0.0187 (11)0.0263 (11)0.0281 (13)−0.0032 (9)0.0028 (10)0.0016 (9)
C13B0.0187 (8)0.0318 (10)0.0284 (10)0.0026 (7)0.0047 (7)0.0048 (9)
C14B0.0076 (8)0.0203 (10)0.0216 (12)−0.0010 (5)0.0027 (5)0.0065 (7)
C15B0.0099 (9)0.0158 (12)0.0177 (13)−0.0001 (5)0.0023 (5)0.0022 (6)
C16B0.0110 (7)0.0216 (9)0.0212 (9)−0.0043 (5)0.0019 (5)0.0069 (6)
C17B0.0165 (8)0.0280 (12)0.0227 (12)−0.0035 (6)0.0017 (6)0.0109 (7)
C18B0.0177 (10)0.0263 (13)0.0188 (11)0.0033 (6)0.0007 (7)0.0082 (9)
C19B0.0140 (10)0.0296 (19)0.0228 (16)0.0054 (8)0.0019 (7)0.0060 (11)
C20B0.0186 (11)0.0198 (18)0.0254 (14)0.0007 (9)0.0084 (7)0.0045 (10)
Geometric parameters (Å, º) top
O1A—C20A1.361 (3)O1X—C20X1.362 (13)
O1A—H1OA0.9812O1X—H1OX0.8201
N1A—C7A1.325 (2)N1X—C7X1.318 (9)
N1A—C1A1.387 (2)N1X—C1X1.405 (7)
N2A—C7A1.370 (2)N2X—C6X1.358 (7)
N2A—C6A1.381 (2)N2X—C7X1.385 (9)
N2A—C14A1.460 (3)N2X—C14X1.461 (12)
N3A—C9A1.389 (2)N3X—C9X1.404 (8)
N3A—C14A1.452 (3)N3X—C14X1.453 (15)
N3A—H3AB0.8600N3X—H3XB0.8600
C1A—C6A1.400 (2)C1X—C2X1.367 (9)
C1A—C2A1.407 (2)C1X—C6X1.383 (9)
C2A—C3A1.394 (3)C2X—C3X1.350 (9)
C2A—H2AA0.9300C2X—H2XA0.9300
C3A—C4A1.404 (4)C3X—C4X1.383 (10)
C3A—H3AA0.9300C3X—H3XA0.9300
C4A—C5A1.393 (3)C4X—C5X1.375 (10)
C4A—H4AA0.9300C4X—H4XA0.9300
C5A—C6A1.390 (3)C5X—C6X1.378 (9)
C5A—H5AA0.9300C5X—H5XA0.9300
C7A—C8A1.446 (3)C7X—C8X1.473 (9)
C8A—C13A1.390 (2)C8X—C9X1.376 (9)
C8A—C9A1.409 (2)C8X—C13X1.384 (9)
C9A—C10A1.403 (2)C9X—C10X1.385 (10)
C10A—C11A1.388 (3)C10X—C11X1.356 (11)
C10A—H10A0.9300C10X—H10C0.9300
C11A—C12A1.395 (3)C11X—C12X1.377 (11)
C11A—H11A0.9300C11X—H11C0.9300
C12A—C13A1.386 (3)C12X—C13X1.378 (10)
C12A—H12A0.9300C12X—H12C0.9300
C13A—H13A0.9300C13X—H13C0.9300
C14A—C15A1.526 (3)C14X—C15X1.514 (14)
C14A—H14A0.9800C14X—H14C0.9800
C15A—C16A1.391 (3)C15X—C16X1.370 (14)
C15A—C20A1.406 (3)C15X—C20X1.392 (13)
C16A—C17A1.399 (5)C16X—C17X1.372 (14)
C16A—H16A0.9300C16X—H16C0.9300
C17A—C18A1.381 (5)C17X—C18X1.371 (15)
C17A—H17A0.9300C17X—H17C0.9300
C18A—C19A1.389 (3)C18X—C19X1.375 (14)
C18A—H18A0.9300C18X—H18C0.9300
C19A—C20A1.398 (3)C19X—C20X1.364 (14)
C19A—H19A0.9300C19X—H19C0.9300
O1B—C20B1.387 (4)O1Y—C20Y1.337 (12)
O1B—H1OB0.9754O1Y—H1OY0.8786
N1B—C7B1.317 (2)N1Y—C7Y1.337 (6)
N1B—C1B1.405 (3)N1Y—C1Y1.382 (5)
N2B—C7B1.367 (2)N2Y—C6Y1.371 (5)
N2B—C6B1.395 (2)N2Y—C7Y1.384 (6)
N2B—C14B1.459 (3)N2Y—C14Y1.451 (12)
N3B—C9B1.381 (2)N3Y—C9Y1.359 (6)
N3B—C14B1.470 (5)N3Y—C14Y1.483 (16)
N3B—H3BB0.8600N3Y—H3YB0.8600
C1B—C2B1.396 (3)C1Y—C2Y1.404 (7)
C1B—C6B1.400 (3)C1Y—C6Y1.417 (7)
C2B—C3B1.369 (4)C2Y—C3Y1.399 (11)
C2B—H2BA0.9300C2Y—H2YA0.9300
C3B—C4B1.403 (4)C3Y—C4Y1.364 (10)
C3B—H3BA0.9300C3Y—H3YA0.9300
C4B—C5B1.404 (4)C4Y—C5Y1.350 (8)
C4B—H4BA0.9300C4Y—H4YA0.9300
C5B—C6B1.379 (3)C5Y—C6Y1.374 (7)
C5B—H5BA0.9300C5Y—H5YA0.9300
C7B—C8B1.458 (3)C7Y—C8Y1.439 (6)
C8B—C9B1.407 (2)C8Y—C13Y1.371 (7)
C8B—C13B1.407 (3)C8Y—C9Y1.409 (7)
C9B—C10B1.399 (3)C9Y—C10Y1.445 (8)
C10B—C11B1.370 (3)C10Y—C11Y1.356 (10)
C10B—H10B0.9300C10Y—H10D0.9300
C11B—C12B1.403 (4)C11Y—C12Y1.412 (16)
C11B—H11B0.9300C11Y—H11D0.9300
C12B—C13B1.397 (4)C12Y—C13Y1.393 (15)
C12B—H12B0.9300C12Y—H12D0.9300
C13B—H13B0.9300C13Y—H13D0.9300
C14B—C15B1.524 (3)C14Y—C15Y1.515 (14)
C14B—H14B0.9800C14Y—H14D0.9800
C15B—C16B1.389 (3)C15Y—C16Y1.376 (14)
C15B—C20B1.398 (4)C15Y—C20Y1.396 (13)
C16B—C17B1.390 (3)C16Y—C17Y1.397 (14)
C16B—H16B0.9300C16Y—H16D0.9300
C17B—C18B1.389 (4)C17Y—C18Y1.376 (14)
C17B—H17B0.9300C17Y—H17D0.9300
C18B—C19B1.384 (5)C18Y—C19Y1.356 (14)
C18B—H18B0.9300C18Y—H18D0.9300
C19B—C20B1.394 (5)C19Y—C20Y1.360 (13)
C19B—H19B0.9300C19Y—H19D0.9300
C20A—O1A—H1OA113.6C20X—O1X—H1OA114.8
C20A—O1A—H1OX113.8C20X—O1X—H1OX115.4
C7A—N1A—C1A105.22 (16)C7X—N1X—C1X103.6 (6)
C7A—N2A—C6A107.32 (15)C6X—N2X—C7X107.4 (6)
C7A—N2A—C14A123.90 (18)C6X—N2X—C14X127.3 (8)
C6A—N2A—C14A128.34 (16)C7X—N2X—C14X124.5 (8)
C9A—N3A—C14A120.86 (15)C9X—N3X—C14X121.7 (8)
C9A—N3A—H3AB119.6C9X—N3X—H3XB119.1
C14A—N3A—H3AB119.6C14X—N3X—H3XB119.1
N1A—C1A—C6A110.06 (15)C2X—C1X—C6X119.1 (6)
N1A—C1A—C2A129.92 (16)C2X—C1X—N1X129.9 (6)
C6A—C1A—C2A120.00 (16)C6X—C1X—N1X111.0 (6)
C3A—C2A—C1A117.34 (17)C3X—C2X—C1X119.3 (7)
C3A—C2A—H2AA121.3C3X—C2X—H2XA120.3
C1A—C2A—H2AA121.3C1X—C2X—H2XA120.3
C2A—C3A—C4A121.92 (18)C2X—C3X—C4X121.5 (8)
C2A—C3A—H3AA119.0C2X—C3X—H3XA119.2
C4A—C3A—H3AA119.0C4X—C3X—H3XA119.2
C5A—C4A—C3A120.9 (2)C5X—C4X—C3X120.6 (7)
C5A—C4A—H4AA119.6C5X—C4X—H4XA119.7
C3A—C4A—H4AA119.6C3X—C4X—H4XA119.7
C6A—C5A—C4A117.10 (19)C4X—C5X—C6X116.8 (6)
C6A—C5A—H5AA121.5C4X—C5X—H5XA121.6
C4A—C5A—H5AA121.5C6X—C5X—H5XA121.6
N2A—C6A—C5A132.06 (17)N2X—C6X—C5X132.0 (7)
N2A—C6A—C1A105.16 (15)N2X—C6X—C1X105.4 (6)
C5A—C6A—C1A122.76 (16)C5X—C6X—C1X122.5 (6)
N1A—C7A—N2A112.2 (2)N1X—C7X—N2X112.5 (6)
N1A—C7A—C8A128.45 (17)N1X—C7X—C8X128.8 (7)
N2A—C7A—C8A119.30 (16)N2X—C7X—C8X118.3 (7)
C13A—C8A—C9A120.70 (15)C9X—C8X—C13X120.6 (6)
C13A—C8A—C7A122.39 (15)C9X—C8X—C7X116.8 (7)
C9A—C8A—C7A116.81 (15)C13X—C8X—C7X122.5 (7)
N3A—C9A—C10A121.76 (15)C8X—C9X—C10X118.5 (6)
N3A—C9A—C8A119.48 (14)C8X—C9X—N3X120.9 (7)
C10A—C9A—C8A118.55 (15)C10X—C9X—N3X120.6 (7)
C11A—C10A—C9A120.09 (16)C11X—C10X—C9X119.9 (8)
C11A—C10A—H10A120.0C11X—C10X—H10C120.0
C9A—C10A—H10A120.0C9X—C10X—H10C120.0
C10A—C11A—C12A120.97 (18)C10X—C11X—C12X122.9 (9)
C10A—C11A—H11A119.5C10X—C11X—H11C118.5
C12A—C11A—H11A119.5C12X—C11X—H11C118.5
C13A—C12A—C11A119.37 (18)C11X—C12X—C13X116.9 (8)
C13A—C12A—H12A120.3C11X—C12X—H12C121.5
C11A—C12A—H12A120.3C13X—C12X—H12C121.5
C12A—C13A—C8A120.32 (16)C12X—C13X—C8X121.1 (7)
C12A—C13A—H13A119.8C12X—C13X—H13C119.4
C8A—C13A—H13A119.8C8X—C13X—H13C119.4
N3A—C14A—N2A107.16 (16)N3X—C14X—N2X106.8 (9)
N3A—C14A—C15A112.9 (2)N3X—C14X—C15X111.3 (13)
N2A—C14A—C15A111.8 (2)N2X—C14X—C15X114.4 (11)
N3A—C14A—H14A108.3N3X—C14X—H14C108.0
N2A—C14A—H14A108.3N2X—C14X—H14C108.0
C15A—C14A—H14A108.3C15X—C14X—H14C108.0
C16A—C15A—C20A119.4 (2)C16X—C15X—C20X115.6 (12)
C16A—C15A—C14A123.6 (2)C16X—C15X—C14X122.2 (13)
C20A—C15A—C14A117.0 (2)C20X—C15X—C14X122.2 (12)
C15A—C16A—C17A120.1 (3)C15X—C16X—C17X125.7 (15)
C15A—C16A—H16A119.9C15X—C16X—H16C117.2
C17A—C16A—H16A119.9C17X—C16X—H16C117.2
C18A—C17A—C16A120.3 (4)C18X—C17X—C16X115.4 (15)
C18A—C17A—H17A119.9C18X—C17X—H17C122.3
C16A—C17A—H17A119.9C16X—C17X—H17C122.3
C17A—C18A—C19A120.3 (3)C17X—C18X—C19X122.0 (15)
C17A—C18A—H18A119.9C17X—C18X—H18C119.0
C19A—C18A—H18A119.9C19X—C18X—H18C119.0
C18A—C19A—C20A120.0 (3)C20X—C19X—C18X119.6 (15)
C18A—C19A—H19A120.0C20X—C19X—H19C120.2
C20A—C19A—H19A120.0C18X—C19X—H19C120.2
O1A—C20A—C19A122.0 (2)O1X—C20X—C19X124.6 (14)
O1A—C20A—C15A118.1 (2)O1X—C20X—C15X114.2 (13)
C19A—C20A—C15A119.9 (2)C19X—C20X—C15X121.2 (13)
C20B—O1B—H1OB108.0C20Y—O1Y—H1OB98.5
C20B—O1B—H1OY115.2C20Y—O1Y—H1OY106.8
C7B—N1B—C1B104.73 (15)C7Y—N1Y—C1Y106.7 (4)
C7B—N2B—C6B107.03 (15)C6Y—N2Y—C7Y109.0 (4)
C7B—N2B—C14B124.6 (2)C6Y—N2Y—C14Y125.9 (8)
C6B—N2B—C14B126.8 (2)C7Y—N2Y—C14Y123.6 (8)
C9B—N3B—C14B121.47 (17)C9Y—N3Y—C14Y120.4 (7)
C9B—N3B—H3BB119.3C9Y—N3Y—H3YB119.8
C14B—N3B—H3BB119.3C14Y—N3Y—H3YB119.8
C2B—C1B—C6B120.02 (18)N1Y—C1Y—C2Y131.2 (4)
C2B—C1B—N1B129.91 (17)N1Y—C1Y—C6Y109.6 (4)
C6B—C1B—N1B110.07 (15)C2Y—C1Y—C6Y119.2 (4)
C3B—C2B—C1B117.3 (2)C3Y—C2Y—C1Y114.3 (6)
C3B—C2B—H2BA121.3C3Y—C2Y—H2YA122.8
C1B—C2B—H2BA121.3C1Y—C2Y—H2YA122.8
C2B—C3B—C4B123.0 (3)C4Y—C3Y—C2Y125.1 (9)
C2B—C3B—H3BA118.5C4Y—C3Y—H3YA117.4
C4B—C3B—H3BA118.5C2Y—C3Y—H3YA117.4
C3B—C4B—C5B119.9 (3)C5Y—C4Y—C3Y120.9 (7)
C3B—C4B—H4BA120.1C5Y—C4Y—H4YA119.6
C5B—C4B—H4BA120.1C3Y—C4Y—H4YA119.6
C6B—C5B—C4B116.8 (2)C4Y—C5Y—C6Y116.9 (5)
C6B—C5B—H5BA121.6C4Y—C5Y—H5YA121.6
C4B—C5B—H5BA121.6C6Y—C5Y—H5YA121.6
C5B—C6B—N2B132.11 (19)N2Y—C6Y—C5Y131.8 (4)
C5B—C6B—C1B122.96 (18)N2Y—C6Y—C1Y104.7 (4)
N2B—C6B—C1B104.92 (17)C5Y—C6Y—C1Y123.5 (4)
N1B—C7B—N2B113.23 (18)N1Y—C7Y—N2Y110.0 (4)
N1B—C7B—C8B128.25 (17)N1Y—C7Y—C8Y130.0 (4)
N2B—C7B—C8B118.49 (15)N2Y—C7Y—C8Y120.0 (4)
C9B—C8B—C13B120.29 (17)C13Y—C8Y—C9Y121.5 (4)
C9B—C8B—C7B116.80 (17)C13Y—C8Y—C7Y123.4 (5)
C13B—C8B—C7B122.79 (16)C9Y—C8Y—C7Y115.1 (5)
N3B—C9B—C10B121.40 (16)N3Y—C9Y—C8Y122.1 (5)
N3B—C9B—C8B119.77 (18)N3Y—C9Y—C10Y120.2 (4)
C10B—C9B—C8B118.70 (17)C8Y—C9Y—C10Y117.5 (5)
C11B—C10B—C9B120.27 (17)C11Y—C10Y—C9Y119.1 (6)
C11B—C10B—H10B119.9C11Y—C10Y—H10D120.4
C9B—C10B—H10B119.9C9Y—C10Y—H10D120.4
C10B—C11B—C12B122.4 (2)C10Y—C11Y—C12Y123.1 (10)
C10B—C11B—H11B118.8C10Y—C11Y—H11D118.4
C12B—C11B—H11B118.8C12Y—C11Y—H11D118.4
C13B—C12B—C11B117.7 (3)C13Y—C12Y—C11Y117.3 (13)
C13B—C12B—H12B121.2C13Y—C12Y—H12D121.4
C11B—C12B—H12B121.2C11Y—C12Y—H12D121.4
C12B—C13B—C8B120.6 (2)C8Y—C13Y—C12Y121.3 (8)
C12B—C13B—H13B119.7C8Y—C13Y—H13D119.3
C8B—C13B—H13B119.7C12Y—C13Y—H13D119.3
N2B—C14B—N3B105.4 (2)N2Y—C14Y—N3Y106.3 (9)
N2B—C14B—C15B111.3 (3)N2Y—C14Y—C15Y112.1 (11)
N3B—C14B—C15B112.6 (3)N3Y—C14Y—C15Y114.5 (15)
N2B—C14B—H14B109.2N2Y—C14Y—H14D107.9
N3B—C14B—H14B109.2N3Y—C14Y—H14D107.9
C15B—C14B—H14B109.2C15Y—C14Y—H14D107.9
C16B—C15B—C20B117.8 (3)C16Y—C15Y—C20Y120.4 (12)
C16B—C15B—C14B123.2 (3)C16Y—C15Y—C14Y122.5 (13)
C20B—C15B—C14B119.0 (3)C20Y—C15Y—C14Y116.9 (11)
C15B—C16B—C17B121.1 (2)C15Y—C16Y—C17Y122.7 (14)
C15B—C16B—H16B119.5C15Y—C16Y—H16D118.7
C17B—C16B—H16B119.5C17Y—C16Y—H16D118.7
C18B—C17B—C16B119.9 (3)C18Y—C17Y—C16Y114.7 (14)
C18B—C17B—H17B120.0C18Y—C17Y—H17D122.7
C16B—C17B—H17B120.0C16Y—C17Y—H17D122.7
C19B—C18B—C17B120.4 (3)C19Y—C18Y—C17Y122.8 (15)
C19B—C18B—H18B119.8C19Y—C18Y—H18D118.6
C17B—C18B—H18B119.8C17Y—C18Y—H18D118.6
C18B—C19B—C20B118.8 (4)C18Y—C19Y—C20Y122.6 (15)
C18B—C19B—H19B120.6C18Y—C19Y—H19D118.7
C20B—C19B—H19B120.6C20Y—C19Y—H19D118.7
O1B—C20B—C19B121.0 (4)O1Y—C20Y—C19Y126.0 (12)
O1B—C20B—C15B116.9 (4)O1Y—C20Y—C15Y115.9 (11)
C19B—C20B—C15B121.9 (4)C19Y—C20Y—C15Y116.5 (12)
C7A—N1A—C1A—C6A−0.70 (19)C7X—N1X—C1X—C2X179.6 (8)
C7A—N1A—C1A—C2A177.60 (18)C7X—N1X—C1X—C6X−1.6 (8)
N1A—C1A—C2A—C3A−178.11 (18)C6X—C1X—C2X—C3X1.4 (10)
C6A—C1A—C2A—C3A0.0 (3)N1X—C1X—C2X—C3X−179.8 (7)
C1A—C2A—C3A—C4A−0.6 (3)C1X—C2X—C3X—C4X−3.1 (12)
C2A—C3A—C4A—C5A0.1 (4)C2X—C3X—C4X—C5X3.0 (13)
C3A—C4A—C5A—C6A0.9 (4)C3X—C4X—C5X—C6X−1.1 (12)
C7A—N2A—C6A—C5A−179.3 (2)C7X—N2X—C6X—C5X−180.0 (8)
C14A—N2A—C6A—C5A8.2 (3)C14X—N2X—C6X—C5X−9.8 (13)
C7A—N2A—C6A—C1A−1.11 (18)C7X—N2X—C6X—C1X2.2 (8)
C14A—N2A—C6A—C1A−173.61 (19)C14X—N2X—C6X—C1X172.4 (9)
C4A—C5A—C6A—N2A176.4 (2)C4X—C5X—C6X—N2X−178.1 (7)
C4A—C5A—C6A—C1A−1.5 (3)C4X—C5X—C6X—C1X−0.6 (10)
N1A—C1A—C6A—N2A1.13 (18)C2X—C1X—C6X—N2X178.5 (6)
C2A—C1A—C6A—N2A−177.36 (15)N1X—C1X—C6X—N2X−0.5 (7)
N1A—C1A—C6A—C5A179.53 (17)C2X—C1X—C6X—C5X0.5 (10)
C2A—C1A—C6A—C5A1.0 (3)N1X—C1X—C6X—C5X−178.5 (6)
C1A—N1A—C7A—N2A0.0 (2)C1X—N1X—C7X—N2X3.0 (9)
C1A—N1A—C7A—C8A−178.26 (18)C1X—N1X—C7X—C8X176.3 (9)
C6A—N2A—C7A—N1A0.7 (2)C6X—N2X—C7X—N1X−3.5 (10)
C14A—N2A—C7A—N1A173.66 (18)C14X—N2X—C7X—N1X−174.0 (9)
C6A—N2A—C7A—C8A179.15 (15)C6X—N2X—C7X—C8X−177.6 (7)
C14A—N2A—C7A—C8A−7.9 (3)C14X—N2X—C7X—C8X11.9 (14)
N1A—C7A—C8A—C13A−6.7 (3)N1X—C7X—C8X—C9X−167.6 (9)
N2A—C7A—C8A—C13A175.20 (16)N2X—C7X—C8X—C9X5.4 (12)
N1A—C7A—C8A—C9A169.64 (17)N1X—C7X—C8X—C13X9.2 (14)
N2A—C7A—C8A—C9A−8.5 (2)N2X—C7X—C8X—C13X−177.8 (7)
C14A—N3A—C9A—C10A−155.79 (17)C13X—C8X—C9X—C10X1.4 (11)
C14A—N3A—C9A—C8A29.6 (2)C7X—C8X—C9X—C10X178.2 (8)
C13A—C8A—C9A—N3A174.43 (15)C13X—C8X—C9X—N3X−175.6 (6)
C7A—C8A—C9A—N3A−2.0 (2)C7X—C8X—C9X—N3X1.2 (10)
C13A—C8A—C9A—C10A−0.4 (2)C14X—N3X—C9X—C8X−25.8 (12)
C7A—C8A—C9A—C10A−176.78 (15)C14X—N3X—C9X—C10X157.3 (9)
N3A—C9A—C10A—C11A−174.50 (17)C8X—C9X—C10X—C11X−1.5 (12)
C8A—C9A—C10A—C11A0.2 (3)N3X—C9X—C10X—C11X175.5 (8)
C9A—C10A—C11A—C12A0.1 (3)C9X—C10X—C11X—C12X2.3 (15)
C10A—C11A—C12A—C13A−0.3 (3)C10X—C11X—C12X—C13X−2.9 (14)
C11A—C12A—C13A—C8A0.1 (3)C11X—C12X—C13X—C8X2.7 (12)
C9A—C8A—C13A—C12A0.2 (3)C9X—C8X—C13X—C12X−2.1 (11)
C7A—C8A—C13A—C12A176.42 (18)C7X—C8X—C13X—C12X−178.8 (8)
C9A—N3A—C14A—N2A−41.4 (2)C9X—N3X—C14X—N2X38.1 (14)
C9A—N3A—C14A—C15A82.0 (2)C9X—N3X—C14X—C15X−87.5 (11)
C7A—N2A—C14A—N3A30.8 (3)C6X—N2X—C14X—N3X159.8 (8)
C6A—N2A—C14A—N3A−157.78 (16)C7X—N2X—C14X—N3X−31.6 (15)
C7A—N2A—C14A—C15A−93.4 (3)C6X—N2X—C14X—C15X−76.5 (16)
C6A—N2A—C14A—C15A78.0 (3)C7X—N2X—C14X—C15X92.1 (14)
N3A—C14A—C15A—C16A−114.4 (3)N3X—C14X—C15X—C16X81.8 (17)
N2A—C14A—C15A—C16A6.5 (4)N2X—C14X—C15X—C16X−39 (2)
N3A—C14A—C15A—C20A66.4 (3)N3X—C14X—C15X—C20X−100.2 (19)
N2A—C14A—C15A—C20A−172.7 (3)N2X—C14X—C15X—C20X138.5 (17)
C20A—C15A—C16A—C17A1.8 (5)C20X—C15X—C16X—C17X0.4 (18)
C14A—C15A—C16A—C17A−177.5 (5)C14X—C15X—C16X—C17X178.5 (19)
C15A—C16A—C17A—C18A−1.6 (8)C15X—C16X—C17X—C18X6.0 (19)
C16A—C17A—C18A—C19A1.3 (9)C16X—C17X—C18X—C19X−8 (3)
C17A—C18A—C19A—C20A−1.3 (8)C17X—C18X—C19X—C20X5 (4)
C18A—C19A—C20A—O1A−179.6 (4)C18X—C19X—C20X—O1X−178 (2)
C18A—C19A—C20A—C15A1.5 (6)C18X—C19X—C20X—C15X2 (3)
C16A—C15A—C20A—O1A179.3 (3)C16X—C15X—C20X—O1X176.0 (17)
C14A—C15A—C20A—O1A−1.5 (5)C14X—C15X—C20X—O1X−2 (3)
C16A—C15A—C20A—C19A−1.7 (5)C16X—C15X—C20X—C19X−5 (3)
C14A—C15A—C20A—C19A177.6 (3)C14X—C15X—C20X—C19X177 (2)
C7B—N1B—C1B—C2B179.5 (2)C7Y—N1Y—C1Y—C2Y−179.7 (5)
C7B—N1B—C1B—C6B0.5 (2)C7Y—N1Y—C1Y—C6Y−0.3 (5)
C6B—C1B—C2B—C3B0.3 (4)N1Y—C1Y—C2Y—C3Y178.9 (7)
N1B—C1B—C2B—C3B−178.6 (3)C6Y—C1Y—C2Y—C3Y−0.5 (9)
C1B—C2B—C3B—C4B−1.0 (6)C1Y—C2Y—C3Y—C4Y2.8 (15)
C2B—C3B—C4B—C5B1.1 (6)C2Y—C3Y—C4Y—C5Y−3.9 (16)
C3B—C4B—C5B—C6B−0.4 (4)C3Y—C4Y—C5Y—C6Y2.3 (10)
C4B—C5B—C6B—N2B178.5 (2)C7Y—N2Y—C6Y—C5Y−179.2 (5)
C4B—C5B—C6B—C1B−0.3 (3)C14Y—N2Y—C6Y—C5Y−12.7 (11)
C7B—N2B—C6B—C5B179.9 (2)C7Y—N2Y—C6Y—C1Y0.9 (5)
C14B—N2B—C6B—C5B14.1 (3)C14Y—N2Y—C6Y—C1Y167.4 (9)
C7B—N2B—C6B—C1B−1.15 (19)C4Y—C5Y—C6Y—N2Y180.0 (5)
C14B—N2B—C6B—C1B−166.9 (2)C4Y—C5Y—C6Y—C1Y−0.1 (7)
C2B—C1B—C6B—C5B0.3 (3)N1Y—C1Y—C6Y—N2Y−0.4 (5)
N1B—C1B—C6B—C5B179.45 (18)C2Y—C1Y—C6Y—N2Y179.1 (4)
C2B—C1B—C6B—N2B−178.71 (17)N1Y—C1Y—C6Y—C5Y179.7 (4)
N1B—C1B—C6B—N2B0.4 (2)C2Y—C1Y—C6Y—C5Y−0.8 (7)
C1B—N1B—C7B—N2B−1.3 (2)C1Y—N1Y—C7Y—N2Y0.9 (5)
C1B—N1B—C7B—C8B−179.37 (17)C1Y—N1Y—C7Y—C8Y−179.6 (5)
C6B—N2B—C7B—N1B1.6 (2)C6Y—N2Y—C7Y—N1Y−1.1 (5)
C14B—N2B—C7B—N1B167.8 (2)C14Y—N2Y—C7Y—N1Y−168.0 (8)
C6B—N2B—C7B—C8B179.87 (15)C6Y—N2Y—C7Y—C8Y179.2 (4)
C14B—N2B—C7B—C8B−13.9 (3)C14Y—N2Y—C7Y—C8Y12.3 (10)
N1B—C7B—C8B—C9B171.53 (17)N1Y—C7Y—C8Y—C13Y4.7 (8)
N2B—C7B—C8B—C9B−6.4 (2)N2Y—C7Y—C8Y—C13Y−175.8 (5)
N1B—C7B—C8B—C13B−4.5 (3)N1Y—C7Y—C8Y—C9Y−172.9 (5)
N2B—C7B—C8B—C13B177.58 (17)N2Y—C7Y—C8Y—C9Y6.6 (7)
C14B—N3B—C9B—C10B−156.83 (19)C14Y—N3Y—C9Y—C8Y−26.8 (10)
C14B—N3B—C9B—C8B27.5 (3)C14Y—N3Y—C9Y—C10Y158.2 (8)
C13B—C8B—C9B—N3B175.78 (17)C13Y—C8Y—C9Y—N3Y−176.8 (5)
C7B—C8B—C9B—N3B−0.3 (2)C7Y—C8Y—C9Y—N3Y0.8 (7)
C13B—C8B—C9B—C10B0.0 (3)C13Y—C8Y—C9Y—C10Y−1.7 (8)
C7B—C8B—C9B—C10B−176.08 (16)C7Y—C8Y—C9Y—C10Y175.9 (5)
N3B—C9B—C10B—C11B−175.40 (18)N3Y—C9Y—C10Y—C11Y176.2 (7)
C8B—C9B—C10B—C11B0.3 (3)C8Y—C9Y—C10Y—C11Y1.0 (10)
C9B—C10B—C11B—C12B−0.7 (3)C9Y—C10Y—C11Y—C12Y2.2 (19)
C10B—C11B—C12B—C13B0.7 (4)C10Y—C11Y—C12Y—C13Y−5 (3)
C11B—C12B—C13B—C8B−0.4 (4)C9Y—C8Y—C13Y—C12Y−0.8 (15)
C9B—C8B—C13B—C12B0.0 (3)C7Y—C8Y—C13Y—C12Y−178.2 (13)
C7B—C8B—C13B—C12B175.9 (2)C11Y—C12Y—C13Y—C8Y4 (3)
C7B—N2B—C14B—N3B35.6 (3)C6Y—N2Y—C14Y—N3Y161.8 (7)
C6B—N2B—C14B—N3B−160.96 (18)C7Y—N2Y—C14Y—N3Y−33.5 (14)
C7B—N2B—C14B—C15B−86.7 (4)C6Y—N2Y—C14Y—C15Y−72.4 (17)
C6B—N2B—C14B—C15B76.7 (4)C7Y—N2Y—C14Y—C15Y92.3 (14)
C9B—N3B—C14B—N2B−42.1 (3)C9Y—N3Y—C14Y—N2Y40.4 (14)
C9B—N3B—C14B—C15B79.4 (3)C9Y—N3Y—C14Y—C15Y−83.9 (11)
N2B—C14B—C15B—C16B6.9 (6)N2Y—C14Y—C15Y—C16Y−41 (2)
N3B—C14B—C15B—C16B−111.1 (4)N3Y—C14Y—C15Y—C16Y80.5 (18)
N2B—C14B—C15B—C20B−175.8 (4)N2Y—C14Y—C15Y—C20Y145.4 (16)
N3B—C14B—C15B—C20B66.1 (5)N3Y—C14Y—C15Y—C20Y−93.4 (19)
C20B—C15B—C16B—C17B1.1 (5)C20Y—C15Y—C16Y—C17Y−1.0 (18)
C14B—C15B—C16B—C17B178.4 (4)C14Y—C15Y—C16Y—C17Y−175 (2)
C15B—C16B—C17B—C18B0.4 (4)C15Y—C16Y—C17Y—C18Y−4.0 (17)
C16B—C17B—C18B—C19B−1.1 (7)C16Y—C17Y—C18Y—C19Y6 (3)
C17B—C18B—C19B—C20B0.3 (9)C17Y—C18Y—C19Y—C20Y−4 (4)
C18B—C19B—C20B—O1B176.0 (6)C18Y—C19Y—C20Y—O1Y−167 (2)
C18B—C19B—C20B—C15B1.3 (10)C18Y—C19Y—C20Y—C15Y−2 (3)
C16B—C15B—C20B—O1B−176.8 (4)C16Y—C15Y—C20Y—O1Y170.4 (15)
C14B—C15B—C20B—O1B5.8 (7)C14Y—C15Y—C20Y—O1Y−16 (2)
C16B—C15B—C20B—C19B−1.9 (8)C16Y—C15Y—C20Y—C19Y4 (3)
C14B—C15B—C20B—C19B−179.3 (6)C14Y—C15Y—C20Y—C19Y177.9 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···N1Bi0.981.692.641 (3)162
N3A—H3AB···O1Aii0.862.503.241 (3)144
O1B—H1OB···N1Aiii0.971.792.686 (4)151
N3B—H3BB···O1Biv0.862.152.974 (4)160
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y+1, −z+1; (iv) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC20H15N3O
Mr313.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)297
a, b, c (Å)17.1513 (10), 19.1160 (11), 9.2630 (5)
β (°) 97.590 (1)
V (Å3)3010.4 (3)
Z8
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.30 × 0.28 × 0.25
Data collection
DiffractometerBruker APEXII DUO CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.974, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections		40861, 11057, 8231
Rint0.047
(sin θ/λ)max (Å−1)0.763
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.158, 1.05
No. of reflections11057
No. of parameters625
No. of restraints144
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.44, −0.42

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···N1Bi0.981.692.641 (3)162
N3A—H3AB···O1Aii0.862.503.241 (3)144
O1B—H1OB···N1Aiii0.971.792.686 (4)151
N3B—H3BB···O1Biv0.862.152.974 (4)160
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y+1, −z+1; (iv) −x+2, −y+1, −z.
 

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant (1001/PKIMIA/815067). NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the Inter­national University of Africa (Sudan) for providing study leave. The authors also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

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ISSN: 2056-9890
Volume 67| Part 9| September 2011| Pages o2243-o2244
doi:10.1107/S1600536811030583
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