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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 12| December 2012| Pages o3311-o3312

1-[4-(Prop-2-en-1-yl­­oxy)benz­yl]-2-[4-(prop-2-en-1-yl­­oxy)phen­yl]-1H-benzimidazole

aUniversity Malaysia Pahang, Faculty of Industrial Sciences and Technology, 26300 Gambang, Kuantan, Pahang, Malaysia, and bDepartment Chemistry, Faculty Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia
*Correspondence e-mail: lutfor73@gmail.com

(Received 1 October 2012; accepted 5 November 2012; online 10 November 2012)

In the title compound, C26H24N2O2, the benzimidazole ring system is almost planar [maximum displacement = 0.025 (1) Å] and makes dihedral angles of 80.48 (5) and 41.57 (5)° with the benzene rings, which are inclined to one another by 65.33 (6)°. In the crystal, mol­ecules are linked via C—H⋯π and weak ππ inter­actions [centroid–centroid distance = 3.8070 (7) Å and inter­planar distance = 3.6160 (5) Å].

Related literature

For the activity of benzimidazole derivatives against viruses, see: Tamm & Sehgal (1978[Tamm, I. & Sehgal, P. B. (1978). Adv. Virus Res. 22, 187-258.]); Porcari et al. (1998[Porcari, A. R., Devivar, R. V., Kucera, L. S., Drach, J. C. & Townsend, L. B. (1998). J. Med. Chem. 41, 1252-1262.]); Migawa et al. (1998[Migawa, M. T., Girardet, J. L., Walker, J. A., Koszalka, G. W., Chamberlain, S. D., Drach, J. C. & Townsend, L. B. (1998). J. Med. Chem. 41, 1242-1251.]). For their other biological activity, see: Spasov et al. (1999[Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.]); Nakano et al. (2000[Nakano, H., Inoue, T., Kawasaki, N., Miyataka, H., Matsumoto, H., Taguchi, T., Inagaki, N., Nagai, H. & Satoh, T. (2000). Bioorg. Med. Chem. 8, 373-380.]); Zhao et al. (2000[Zhao, Z. S., Arnaiz, D. O., Griedel, B., Sakata, S., Dallas, J. L., Whitlow, M., Trinh, L., Post, J., Liang, A., Morrissey, M. M. & Shaw, K. J. (2000). Bioorg. Med. Chem. Lett. 10, 963-966.]); White et al. (2000[White, A. W., Almassy, R., Calvert, A. H., Curtin, N. J., Griffin, R. J., Hostomsky, Z., Maegley, K., Newell, D. R., Srinivasan, S. & Golding, B. T. (2000). J. Med. Chem. 43, 4084-4097.]); Xiangming et al. (2007[Xiangming, H., Huiqiang, M. & Yulu, W. (2007). ARKIVOC, pp. 150-154.]). For related structures, see: Kia et al. (2009[Kia, R., Fun, H.-K. & Kargar, H. (2009). Acta Cryst. E65, o660-o661.]); Zhou et al. (2009[Zhou, J.-C., Zhang, Z.-Y., Li, N.-X. & Zhang, C.-M. (2009). Acta Cryst. E65, o3019.]). For synthetic details, see: Lutfor et al. (2008[Lutfor, M. R., Jahimin, A., Sandeep, K. & Tschierske, C. (2008). Liq. Cryst. 35, 1263-1270.]). For standard bond lengths, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24N2O2

  • Mr = 396.49

  • Monoclinic, P 21 /n

  • a = 12.5455 (1) Å

  • b = 10.1989 (1) Å

  • c = 15.9340 (2) Å

  • β = 99.5027 (11)°

  • V = 2010.78 (4) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.66 mm−1

  • T = 100 K

  • 0.35 × 0.23 × 0.08 mm

Data collection
  • Agilent Technologies Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.80, Tmax = 0.95

  • 38976 measured reflections

  • 3908 independent reflections

  • 3563 reflections with I > 2.0σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.100

  • S = 0.99

  • 3891 reflections

  • 271 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C5/C26/C27 ring; Cg3 is the centroid of the C10–C15 ring and Cg4 is the centroid of the C16–C19/C24/25 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H121⋯Cg4i 0.97 2.62 3.5064 (13) 153
C23—H231⋯Cg3ii 0.96 2.73 3.6859 (15) 175
C30—H301⋯Cg2iii 0.95 2.72 3.6202 (14) 159
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x, -y+1, -z+1; (iii) [-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: CRYSTALS.

Supporting information


Comment top

The importance of the benzimidazole nucleus is due to the fact that it is found in many biologically active compounds (Xiangming et al., 2007). Benzimidazole derivatives have been shown to have significant activity against several viruses such as, HIV (Porcari et al., 1998), herpes (Migawa et al., 1998), influenza (Tamm and Sehgal, 1978) and human cytomegalovirus (Porcari et al., 1998). Many benzimidazole containing compounds exhibited significant biological activities, such as novel anti-allergic agents (Nakano et al., 2000), factor Xa inhibitors (Zhao et al., 2000), poly (ADP-ribose) polymerase (PARP) inhibitors (White et al., 2000). Some substituted benzimidazole derivatives have been recently commercialized for applications in veterinarian medicine, and in diverse human therapeutic areas such as, the treatment of ulcers and as antihistamines (Spasov et al., 1999).

In the titled compound (Fig. 1) the bond lengths (Allen et al., 1987) and bond angles are normal. The benzimidazole ring system (N7/C8/N9/C10-C15) is almost planar, with a maximum displacement of 0.025 (1) Å for atom C8. The dihedral angle formed by the mean plane of the benzimidazole ring system and the two adjacent benzene rings (C2-C5/C26/C27 and C16-C19/C24/C25) are 80.48 (5)° and 41.57 (5)°, respectively. The benzene rings themselves are inclined to one another by 65.33 (6)°, rather than ca. 90° as observed elsewhere, for example in the related compounds, 4-[1-(4-Cyanobenzyl)-1H-benzimidazol-2-yl]benzonitrile (Kia et al., 2009) and 1-(4-tert-Butylbenzyl)-2-(4-tert-butylphenyl)-1H-benzimidazole (Zhou et al., 2009). The torsion angles of the allyloxy chains (O1-C28-C29-C30 and O20-C21-C22-C23) are 133.16 (13)° and 120.11 (14)°, respectively.

In the crystal, molecules are linked via C-H···π interactions (Table 1) and weak π-π interactions. The centroid to centroid distance, Cg1···Cg2i, is 3.8070 (7)Å with an interplanar distance of 3.6160 (5) Å [Cg1 and Cg2 are the centroids of the N7/C8/N9/C10/C11 and C2-C5/C26/C27 rings; symmetry code: (i) -x + 1/2, y + 1/2, -z + 3/2].

Related literature top

For the activity of benzimidazole derivatives against viruses, see: Tamm & Sehgal (1978); Porcari et al. (1998); Migawa et al. (1998). For their other biological activity, see: Spasov et al. (1999); Nakano et al. (2000); Zhao et al. (2000); White et al. (2000); Xiangming et al. (2007). For related structures, see: Kia et al. (2009); Zhou et al. (2009). For synthetic details, see: Lutfor et al. (2008). For standard bond lengths, see Allen et al. (1987).

Experimental top

4-Hydroxybenzaldehyde (10.0 g, 83.25 mmol) was dissolved in dry acetone (150 mL). Then allyl bromide (12.097 g, 100 mmol), potassium carbonate (13.80 g, 100 mmol) and a catalytic amount of potassium iodide (20 mg) were added and the mixture was refluxed for 24 h under argon atmosphere. Afterwards, it was poured into ice-cold water and acidified with dilute hydrochloric acid (pH<5). The precipitate was filtered off and was crystallized from methanol/chloroform to yield the 4-(prop-2-en-1-yloxy)benzaldehyde. A solution of 4-(prop-2-en-1-yloxy)benzaldehyde (5.00 g, 30.82 mmol) in ethanol was added to a solution of o-phenylenediamine (1.66 g, 15.41 mmol) in ethanol. The mixture was refluxed with a few drops of acetic acid as catalyst for 12 h to yield the title compound as a slightly grey solid. The product was filtered off and recrystallized from absolute ethanol to give pale-brown block-like crystals of the title compound, suitable for X-ray diffraction analysis (Lutfor et al., 2008).

Refinement top

The H atoms were all located in a difference Fourier map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98 Å, N—H in the range 0.86–0.90 Å) and Uiso(H) in the range 1.2–1.5 times Ueq of the parent atom). In the final cycles of refinement they were refined as riding atoms.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level.
1-[4-(Prop-2-en-1-yloxy)benzyl]-2-[4-(prop-2-en-1-yloxy)phenyl]- 1H-benzimidazole top
Crystal data top
C26H24N2O2F(000) = 840
Mr = 396.49Dx = 1.310 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ynCell parameters from 17352 reflections
a = 12.5455 (1) Åθ = 4–71°
b = 10.1989 (1) ŵ = 0.66 mm1
c = 15.9340 (2) ÅT = 100 K
β = 99.5027 (11)°Block, pale brown
V = 2010.78 (4) Å30.35 × 0.23 × 0.08 mm
Z = 4
Data collection top
Agilent Technologies Gemini
diffractometer
3908 independent reflections
Radiation source: sealed x-ray tube3563 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 71.4°, θmin = 4.2°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
h = 1515
Tmin = 0.80, Tmax = 0.95k = 1212
38976 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.100 Method = Modified Sheldrick w = 1/[σ2(F2) + (0.06P)2 + 1.04P],
where P = (max(Fo2,0) + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.002
3891 reflectionsΔρmax = 0.26 e Å3
271 parametersΔρmin = 0.25 e Å3
0 restraints
Crystal data top
C26H24N2O2V = 2010.78 (4) Å3
Mr = 396.49Z = 4
Monoclinic, P21/nCu Kα radiation
a = 12.5455 (1) ŵ = 0.66 mm1
b = 10.1989 (1) ÅT = 100 K
c = 15.9340 (2) Å0.35 × 0.23 × 0.08 mm
β = 99.5027 (11)°
Data collection top
Agilent Technologies Gemini
diffractometer
3908 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
3563 reflections with I > 2.0σ(I)
Tmin = 0.80, Tmax = 0.95Rint = 0.029
38976 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 0.99Δρmax = 0.26 e Å3
3891 reflectionsΔρmin = 0.25 e Å3
271 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.10938 (7)0.03132 (9)0.75160 (6)0.0210 (3)
O200.08975 (7)0.86587 (8)0.53875 (6)0.0204 (3)
N70.26914 (8)0.41707 (10)0.66850 (6)0.0168 (3)
N90.32584 (8)0.49128 (10)0.55014 (7)0.0187 (3)
C20.02893 (10)0.12293 (12)0.75473 (8)0.0183 (3)
C30.01085 (10)0.22357 (13)0.81468 (8)0.0207 (3)
C40.06903 (10)0.31589 (13)0.80889 (8)0.0205 (3)
C50.13284 (9)0.30980 (12)0.74543 (7)0.0174 (3)
C60.21706 (10)0.41599 (12)0.74388 (7)0.0180 (3)
C80.25200 (10)0.50155 (12)0.59986 (8)0.0169 (3)
C100.39729 (10)0.39581 (12)0.58841 (8)0.0180 (3)
C110.36292 (9)0.34893 (12)0.66226 (8)0.0174 (3)
C120.41964 (10)0.25513 (12)0.71540 (8)0.0207 (3)
C130.51416 (10)0.20871 (13)0.69185 (9)0.0233 (4)
C140.55011 (10)0.25460 (13)0.61838 (9)0.0227 (4)
C150.49311 (10)0.34782 (12)0.56574 (8)0.0208 (3)
C160.16006 (10)0.59333 (12)0.58484 (7)0.0170 (3)
C170.17631 (10)0.72115 (12)0.55660 (7)0.0181 (3)
C180.09167 (10)0.80926 (12)0.54134 (8)0.0185 (3)
C190.01170 (10)0.77117 (12)0.55381 (7)0.0172 (3)
C210.19187 (10)0.83706 (13)0.56480 (8)0.0218 (4)
C220.25815 (10)0.95958 (13)0.55465 (8)0.0211 (3)
C230.35254 (11)0.96766 (14)0.50457 (9)0.0262 (4)
C240.02971 (10)0.64406 (12)0.58006 (8)0.0181 (3)
C250.05619 (10)0.55642 (12)0.59561 (7)0.0180 (3)
C260.11566 (10)0.20690 (12)0.68709 (8)0.0190 (3)
C270.03538 (10)0.11448 (12)0.69133 (8)0.0196 (3)
C280.18801 (10)0.05439 (13)0.80606 (8)0.0212 (3)
C290.27537 (10)0.04607 (13)0.78754 (8)0.0208 (3)
C300.31212 (10)0.11109 (13)0.84837 (9)0.0229 (4)
H310.053500.229200.860000.0269*
H410.080400.386800.849600.0251*
H610.274300.404300.793400.0235*
H620.182600.502400.747400.0230*
H1210.396100.225900.767100.0255*
H1310.555800.143100.727600.0285*
H1410.617500.220600.605300.0280*
H1510.518800.378400.515600.0261*
H1710.249000.747700.549500.0226*
H1810.102600.896800.522200.0235*
H2110.229500.765700.528900.0264*
H2120.178800.809300.626700.0282*
H2210.228501.036900.587400.0259*
H2310.380100.894200.469900.0337*
H2320.394701.046700.501200.0328*
H2410.101800.615800.586400.0238*
H2510.043100.468100.613200.0223*
H2610.158100.202300.641600.0234*
H2710.022800.043200.650500.0239*
H2810.220600.143900.794400.0266*
H2820.153900.048700.867200.0255*
H2910.307100.060000.727800.0250*
H3010.369800.172300.835600.0284*
H3020.278400.096700.906600.0289*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0197 (4)0.0206 (4)0.0237 (5)0.0026 (3)0.0067 (4)0.0017 (4)
O200.0186 (4)0.0183 (4)0.0248 (5)0.0026 (3)0.0054 (3)0.0036 (3)
N70.0171 (5)0.0166 (5)0.0167 (5)0.0001 (4)0.0027 (4)0.0015 (4)
N90.0188 (5)0.0188 (5)0.0189 (5)0.0005 (4)0.0040 (4)0.0009 (4)
C20.0165 (6)0.0176 (6)0.0202 (6)0.0009 (5)0.0010 (5)0.0044 (5)
C30.0208 (6)0.0250 (6)0.0170 (6)0.0007 (5)0.0048 (5)0.0012 (5)
C40.0225 (6)0.0224 (6)0.0163 (6)0.0005 (5)0.0020 (5)0.0018 (5)
C50.0167 (6)0.0184 (6)0.0164 (6)0.0022 (5)0.0010 (4)0.0040 (5)
C60.0198 (6)0.0193 (6)0.0149 (6)0.0002 (5)0.0029 (5)0.0009 (5)
C80.0193 (6)0.0153 (6)0.0155 (6)0.0022 (5)0.0010 (5)0.0004 (4)
C100.0190 (6)0.0155 (6)0.0190 (6)0.0020 (5)0.0014 (5)0.0011 (5)
C110.0166 (6)0.0158 (6)0.0193 (6)0.0017 (5)0.0012 (5)0.0020 (5)
C120.0217 (6)0.0179 (6)0.0211 (6)0.0014 (5)0.0002 (5)0.0018 (5)
C130.0216 (6)0.0182 (6)0.0276 (7)0.0019 (5)0.0032 (5)0.0004 (5)
C140.0162 (6)0.0211 (6)0.0302 (7)0.0003 (5)0.0023 (5)0.0062 (5)
C150.0200 (6)0.0194 (6)0.0234 (6)0.0025 (5)0.0051 (5)0.0034 (5)
C160.0201 (6)0.0178 (6)0.0126 (5)0.0009 (5)0.0012 (4)0.0012 (4)
C170.0190 (6)0.0200 (6)0.0155 (6)0.0011 (5)0.0035 (4)0.0000 (5)
C180.0229 (6)0.0157 (6)0.0170 (6)0.0006 (5)0.0035 (5)0.0015 (5)
C190.0194 (6)0.0180 (6)0.0137 (5)0.0022 (5)0.0011 (4)0.0012 (4)
C210.0176 (6)0.0221 (6)0.0262 (7)0.0002 (5)0.0049 (5)0.0028 (5)
C220.0222 (6)0.0210 (6)0.0209 (6)0.0004 (5)0.0063 (5)0.0009 (5)
C230.0242 (7)0.0251 (7)0.0285 (7)0.0027 (5)0.0019 (5)0.0005 (5)
C240.0171 (6)0.0194 (6)0.0173 (6)0.0013 (5)0.0015 (4)0.0007 (5)
C250.0220 (6)0.0154 (6)0.0158 (6)0.0014 (5)0.0008 (5)0.0005 (4)
C260.0187 (6)0.0205 (6)0.0185 (6)0.0023 (5)0.0051 (5)0.0014 (5)
C270.0205 (6)0.0179 (6)0.0202 (6)0.0019 (5)0.0030 (5)0.0019 (5)
C280.0200 (6)0.0223 (6)0.0223 (6)0.0003 (5)0.0068 (5)0.0001 (5)
C290.0187 (6)0.0228 (6)0.0205 (6)0.0015 (5)0.0023 (5)0.0016 (5)
C300.0207 (6)0.0230 (6)0.0251 (7)0.0018 (5)0.0040 (5)0.0030 (5)
Geometric parameters (Å, º) top
O1—C21.3702 (15)C24—C251.3905 (18)
O1—C281.4367 (16)C26—C271.3892 (18)
O20—C191.3681 (15)C28—C291.4937 (18)
O20—C211.4407 (16)C29—C301.3188 (19)
N7—C61.4590 (15)C3—H310.9700
N7—C81.3810 (16)C4—H410.9700
N7—C111.3841 (15)C6—H610.9800
N9—C81.3187 (16)C6—H620.9900
N9—C101.3939 (16)C12—H1210.9700
C2—C31.3950 (18)C13—H1310.9700
C2—C271.3957 (18)C14—H1410.9700
C3—C41.3892 (18)C15—H1510.9600
C4—C51.3908 (17)C17—H1710.9800
C5—C61.5161 (17)C18—H1810.9600
C5—C261.3949 (17)C21—H2111.0000
C8—C161.4740 (18)C21—H2121.0100
C10—C111.4024 (18)C22—H2210.9800
C10—C151.3995 (18)C23—H2310.9600
C11—C121.3927 (17)C23—H2320.9600
C12—C131.3849 (18)C24—H2410.9700
C13—C141.4026 (19)C25—H2510.9700
C14—C151.3859 (18)C26—H2610.9700
C16—C171.4049 (17)C27—H2710.9700
C16—C251.3939 (18)C28—H2811.0000
C17—C181.3816 (18)C28—H2821.0000
C18—C191.3990 (18)C29—H2910.9800
C19—C241.3921 (17)C30—H3010.9500
C21—C221.4949 (19)C30—H3020.9700
C22—C231.3167 (19)
C2—O1—C28116.19 (10)C5—C4—H41119.00
C19—O20—C21116.76 (9)N7—C6—H61107.00
C6—N7—C8128.63 (10)N7—C6—H62107.00
C6—N7—C11123.84 (10)C5—C6—H61109.00
C8—N7—C11106.23 (10)C5—C6—H62109.00
C8—N9—C10104.92 (10)H61—C6—H62109.00
O1—C2—C3124.21 (11)C11—C12—H121122.00
O1—C2—C27116.22 (11)C13—C12—H121121.00
C3—C2—C27119.54 (11)C12—C13—H131119.00
C2—C3—C4119.39 (12)C14—C13—H131120.00
C3—C4—C5121.74 (12)C13—C14—H141118.00
C4—C5—C6117.79 (11)C15—C14—H141120.00
C4—C5—C26118.29 (11)C10—C15—H151121.00
C6—C5—C26123.92 (10)C14—C15—H151121.00
N7—C6—C5115.27 (10)C16—C17—H171119.00
N7—C8—N9113.16 (11)C18—C17—H171120.00
N7—C8—C16122.69 (11)C17—C18—H181121.00
N9—C8—C16124.15 (11)C19—C18—H181119.00
N9—C10—C11109.92 (11)O20—C21—H211110.00
N9—C10—C15130.48 (11)O20—C21—H212109.00
C11—C10—C15119.57 (11)C22—C21—H211110.00
N7—C11—C10105.77 (10)C22—C21—H212110.00
N7—C11—C12131.02 (11)H211—C21—H212110.00
C10—C11—C12123.18 (11)C21—C22—H221117.00
C11—C12—C13116.39 (12)C23—C22—H221120.00
C12—C13—C14121.32 (12)C22—C23—H231120.00
C13—C14—C15121.95 (12)C22—C23—H232121.00
C10—C15—C14117.59 (12)H231—C23—H232119.00
C8—C16—C17119.36 (11)C19—C24—H241121.00
C8—C16—C25122.07 (11)C25—C24—H241120.00
C17—C16—C25118.56 (11)C16—C25—H251120.00
C16—C17—C18120.79 (12)C24—C25—H251119.00
C17—C18—C19119.86 (11)C5—C26—H261119.00
O20—C19—C18115.62 (11)C27—C26—H261120.00
O20—C19—C24124.28 (11)C2—C27—H271119.00
C18—C19—C24120.10 (11)C26—C27—H271121.00
O20—C21—C22107.67 (10)O1—C28—H281110.00
C21—C22—C23123.12 (12)O1—C28—H282111.00
C19—C24—C25119.52 (12)C29—C28—H281109.00
C16—C25—C24121.15 (11)C29—C28—H282110.00
C5—C26—C27120.77 (11)H281—C28—H282109.00
C2—C27—C26120.24 (11)C28—C29—H291117.00
O1—C28—C29108.84 (10)C30—C29—H291120.00
C28—C29—C30122.26 (12)C29—C30—H301121.00
C2—C3—H31120.00C29—C30—H302119.00
C4—C3—H31120.00H301—C30—H302120.00
C3—C4—H41119.00
C28—O1—C2—C39.44 (17)C4—C5—C26—C271.28 (18)
C28—O1—C2—C27168.51 (11)N9—C8—C16—C1740.64 (17)
C2—O1—C28—C29173.88 (10)N7—C8—C16—C2542.45 (17)
C21—O20—C19—C18169.69 (10)N7—C8—C16—C17139.28 (12)
C21—O20—C19—C2410.16 (16)N9—C8—C16—C25137.63 (13)
C19—O20—C21—C22171.61 (10)N9—C10—C15—C14177.71 (13)
C6—N7—C11—C10168.56 (11)C11—C10—C15—C140.06 (19)
C8—N7—C11—C100.61 (13)C15—C10—C11—C120.17 (19)
C6—N7—C11—C129.7 (2)N9—C10—C11—N70.11 (14)
C8—N7—C11—C12177.59 (13)N9—C10—C11—C12178.27 (11)
C8—N7—C6—C5104.28 (14)C15—C10—C11—N7178.21 (11)
C11—N7—C6—C590.59 (14)N7—C11—C12—C13177.85 (13)
C6—N7—C8—N9168.14 (11)C10—C11—C12—C130.08 (19)
C11—N7—C8—N90.97 (14)C11—C12—C13—C140.11 (19)
C6—N7—C8—C1611.79 (19)C12—C13—C14—C150.2 (2)
C11—N7—C8—C16178.95 (11)C13—C14—C15—C100.1 (2)
C10—N9—C8—N70.88 (14)C8—C16—C17—C18179.53 (11)
C10—N9—C8—C16179.04 (11)C25—C16—C17—C181.20 (17)
C8—N9—C10—C110.46 (14)C8—C16—C25—C24179.18 (11)
C8—N9—C10—C15177.37 (13)C17—C16—C25—C240.90 (17)
O1—C2—C3—C4176.16 (12)C16—C17—C18—C190.19 (18)
O1—C2—C27—C26176.99 (11)C17—C18—C19—O20178.71 (11)
C27—C2—C3—C41.74 (19)C17—C18—C19—C241.16 (18)
C3—C2—C27—C261.07 (19)O20—C19—C24—C25178.39 (11)
C2—C3—C4—C50.92 (19)C18—C19—C24—C251.46 (18)
C3—C4—C5—C6179.34 (11)O20—C21—C22—C23120.11 (14)
C3—C4—C5—C260.59 (19)C19—C24—C25—C160.42 (18)
C4—C5—C6—N7170.42 (11)C5—C26—C27—C20.46 (19)
C6—C5—C26—C27178.65 (11)O1—C28—C29—C30133.16 (13)
C26—C5—C6—N79.50 (17)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C2–C5/C26/C27 ring; Cg3 is the centroid of the C10–C15 ring and Cg4 is the centroid of the C16–C19/C24/25 ring.
D—H···AD—HH···AD···AD—H···A
C12—H121···Cg4i0.972.623.5064 (13)153
C23—H231···Cg3ii0.962.733.6859 (15)175
C30—H301···Cg2iii0.952.723.6202 (14)159
Symmetry codes: (i) x+1/2, y1/2, z+3/2; (ii) x, y+1, z+1; (iii) x1/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC26H24N2O2
Mr396.49
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)12.5455 (1), 10.1989 (1), 15.9340 (2)
β (°) 99.5027 (11)
V3)2010.78 (4)
Z4
Radiation typeCu Kα
µ (mm1)0.66
Crystal size (mm)0.35 × 0.23 × 0.08
Data collection
DiffractometerAgilent Technologies Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.80, 0.95
No. of measured, independent and
observed [I > 2.0σ(I)] reflections
38976, 3908, 3563
Rint0.029
(sin θ/λ)max1)0.615
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.100, 0.99
No. of reflections3891
No. of parameters271
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.25

Computer programs: CrysAlis PRO (Agilent, 2011), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C2–C5/C26/C27 ring; Cg3 is the centroid of the C10–C15 ring and Cg4 is the centroid of the C16–C19/C24/25 ring.
D—H···AD—HH···AD···AD—H···A
C12—H121···Cg4i0.972.623.5064 (13)153
C23—H231···Cg3ii0.962.733.6859 (15)175
C30—H301···Cg2iii0.952.723.6202 (14)159
Symmetry codes: (i) x+1/2, y1/2, z+3/2; (ii) x, y+1, z+1; (iii) x1/2, y1/2, z+3/2.
 

Acknowledgements

This research was supported by a UMP research grant (No. RDU100338).

References

First citationAgilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science
First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals
First citationBetteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  Web of Science CrossRef IUCr Journals
First citationKia, R., Fun, H.-K. & Kargar, H. (2009). Acta Cryst. E65, o660–o661.  Web of Science CSD CrossRef IUCr Journals
First citationLutfor, M. R., Jahimin, A., Sandeep, K. & Tschierske, C. (2008). Liq. Cryst. 35, 1263–1270.
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS IUCr Journals
First citationMigawa, M. T., Girardet, J. L., Walker, J. A., Koszalka, G. W., Chamberlain, S. D., Drach, J. C. & Townsend, L. B. (1998). J. Med. Chem. 41, 1242–1251.  Web of Science CrossRef CAS PubMed
First citationNakano, H., Inoue, T., Kawasaki, N., Miyataka, H., Matsumoto, H., Taguchi, T., Inagaki, N., Nagai, H. & Satoh, T. (2000). Bioorg. Med. Chem. 8, 373–380.  Web of Science CrossRef PubMed CAS
First citationPorcari, A. R., Devivar, R. V., Kucera, L. S., Drach, J. C. & Townsend, L. B. (1998). J. Med. Chem. 41, 1252–1262.  Web of Science CrossRef CAS PubMed
First citationSpasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232–243.  CrossRef CAS
First citationTamm, I. & Sehgal, P. B. (1978). Adv. Virus Res. 22, 187–258.  CrossRef CAS PubMed
First citationWhite, A. W., Almassy, R., Calvert, A. H., Curtin, N. J., Griffin, R. J., Hostomsky, Z., Maegley, K., Newell, D. R., Srinivasan, S. & Golding, B. T. (2000). J. Med. Chem. 43, 4084–4097.  Web of Science CrossRef PubMed CAS
First citationXiangming, H., Huiqiang, M. & Yulu, W. (2007). ARKIVOC, pp. 150–154.  CrossRef
First citationZhao, Z. S., Arnaiz, D. O., Griedel, B., Sakata, S., Dallas, J. L., Whitlow, M., Trinh, L., Post, J., Liang, A., Morrissey, M. M. & Shaw, K. J. (2000). Bioorg. Med. Chem. Lett. 10, 963–966.  Web of Science CrossRef PubMed CAS
First citationZhou, J.-C., Zhang, Z.-Y., Li, N.-X. & Zhang, C.-M. (2009). Acta Cryst. E65, o3019.  Web of Science CSD CrossRef IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 12| December 2012| Pages o3311-o3312
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds