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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 7| July 2010| Pages o1590-o1591

Ethyl 1-(2-hy­dr­oxy­eth­yl)-2-p-tolyl-1H-benzimidazole-5-carboxyl­ate

aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDivision of Advanced Drug Delivery, Malaysian Institute of Pharmaceuticals and Nutraceuticals, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 26 May 2010; accepted 1 June 2010; online 5 June 2010)

The asymmetric unit of the title compound, C19H20N2O3, contains two mol­ecules (A and B) with slightly different orientations of the ethyl groups with respect to the attached carboxyl­ate groups. Intra­molecular C—H⋯O hydrogen bonds generate S(8) ring motifs in both mol­ecules A and B. In each mol­ecule, the benzimidazole ring system is essentially planar, with maximum deviations of 0.023 (1) and 0.020 (1) Å, respectively, for mol­ecules A and B. The dihedral angle between the benzimidazole ring system and the phenyl ring is 37.34 (5)° for mol­ecule A and 42.42 (5)° for mol­ecule B. In the crystal, O—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules into [100] columns with a cross-section of two-mol­ecule by two-mol­ecule wide, and further stabilization is provided by weak C—H⋯π and ππ inter­actions [centroid separations = 3.5207 (7) and 3.6314 (8) Å].

Related literature

For general background to and applications of benzimidazole derivatives, see: Denny et al. (1990[Denny, W. A., Rewcastle, G. W. & Banguly, B. C. (1990). J. Med. Chem. 33, 814-819.]); Evans et al. (1997[Evans, T. M., Gardiner, J. M., Mahmood, N. & Smis, M. (1997). Bioorg. Med. Chem. Lett. 7, 409-412.]); Grassmann et al. (2002[Grassmann, S., Sadek, B., Ligneau, X., Elz, S., Ganellin, C. R., Arrang, J. M., Schwartz, J. C., Stark, H. & Schunack, W. (2002). Eur. J. Pharm. Sci. 15, 367-378.]); Göker et al. (2002[Göker, H., Kuş, C., Boykin, D. W., Yildiz, S. & Atlanlar, N. (2002). Bioorg. Med. Chem. 10, 2589-2596.]); Seth et al. (2003[Seth, P. P., Jefferson, E. A., Risen, L. M. & Osgood, S. A. (2003). Bioorg. Med. Chem. Lett. 13, 1669-1672.]). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For closely related benzimidazole structures, see: Arumugam et al. (2010a[Arumugam, N., Abdul Rahim, A. S., Abd Hamid, S., Hemamalini, M. & Fun, H.-K. (2010a). Acta Cryst. E66, o796-o797.],b[Arumugam, N., Abdul Rahim, A. S., Osman, H., Hemamalini, M. & Fun, H.-K. (2010b). Acta Cryst. E66, o845.],c[Arumugam, N., Abdul Rahim, A. S., Osman, H., Yeap, C. S. & Fun, H.-K. (2010c). Acta Cryst. E66, o1214-o1215.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C19H20N2O3

  • Mr = 324.37

  • Triclinic, [P \overline 1]

  • a = 9.0400 (9) Å

  • b = 12.6806 (13) Å

  • c = 15.5504 (17) Å

  • α = 74.170 (2)°

  • β = 74.360 (2)°

  • γ = 76.721 (2)°

  • V = 1627.9 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.41 × 0.32 × 0.23 mm

Data collection
  • Bruker APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.964, Tmax = 0.980

  • 30776 measured reflections

  • 10646 independent reflections

  • 8773 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.194

  • S = 1.13

  • 10646 reflections

  • 445 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.60 e Å−3

  • Δρmin = −0.65 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1B/C7B/N2B/C8B/C13B 4,5-dihydro imidazole ring.

D—H⋯A D—H H⋯A DA D—H⋯A
O3A—H1OA⋯N1B 0.96 (3) 1.83 (3) 2.7847 (14) 173 (2)
O3B—H1OB⋯N1A 0.81 (2) 2.08 (2) 2.8859 (15) 172 (3)
C1A—H1AA⋯O3A 0.93 2.37 3.2473 (16) 156
C1B—H1BA⋯O3B 0.93 2.36 3.2331 (16) 157
C12B—H12B⋯O3Ai 0.93 2.45 3.2788 (16) 149
C15B—H15C⋯O1Bii 0.97 2.55 3.2889 (17) 133
C18A—H18A⋯O1Aiii 0.97 2.58 3.1928 (16) 121
C17B—H17CCg1iv 0.97 2.70 3.4194 (13) 131
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+1; (iii) x+1, y, z; (iv) -x+1, -y+1, -z.

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

Benzimidazoles are known to exhibit anti-HIV (Evans et al., 1997), anti-fungal (Göker et al., 2002) and anti-parasitic (Seth et al., 2003) activities. In particular, substituted benzimidazoles have proven as drug leads, generating pharmacological interests (Grassmann et al., 2002). A series of substituted benzimidazole derivatives have been synthesised and evaluated for in vitro and in vivo anti-tumor activity and DNA binding affinity (Denny et al., 1990). Due to their importance, the crystal structure determination of the title compound was carried out and the results are presented in this paper.

The asymmetric unit of the title benzimidazole compound (Fig. 1) comprises of two crystallographically independent molecules, designated A and B. A superposition of the non-H atoms of molecules A and B (Fig. 2) using XP in SHELXTL (Sheldrick, 2008), gave an r.m.s. deviation of 0.517 Å. Molecules A and B differ slightly in the orientation of the ethyl groups (C15 and C16) with respect to the attached carboxylate groups, as can be seen in Fig. 2. The torsion angles C14A–O2A–C15A–C16A and C14B–O2B–C15B–C16B are -77.41 (15) and -171.37 (10)°, respectively.

Intramolecular C1A—H1AA···O3A and C1B—H1BA···O3B hydrogen bonds generate eight-membered rings, producing S(8) ring motifs (Bernstein, 1995). In each molecule, the benzimidazole ring system (C7-C13/N1/N2) are essentially planar, with maximum deviations of 0.023 (1) and -0.020 (1) Å, respectively, at atoms C7A of molecule A and C8B of molecule B. In molecule A, the benzimidazole ring system is inclined at dihedral angle of 37.34 (5)° with the C1A-C6A phenyl ring; the respective angle for molecule B is 42.42 (5)°. The geometric parameters are comparable to those reported in closely related benzimidazole structures (Arumugam et al., 2010a,b,c).

In the crystal packing (Fig. 3), intermolecular O3A—H1OA···N1B, O3B—H1OB···N1A, C12B—H12B···O3A, C15B—H15C···O1B and C18A—H18A···O1A hydrogen bonds link the molecules into columns with cross-section of two-molecule by two-molecule wide along the a axis. The crystal packing is further stabilized by intermolecular C17B—H17C···Cg1 interactions (Table 1) as well as weak ππ aromatic stacking interactions [Cg1···Cg2 = 3.5207 (7) and Cg3···Cg4 = 3.6314 (8) Å; symmetry code: x, y, z; Cg1 and Cg2 are the centroids of 4,5-dihydroimidazole rings (C7A/N1A/C8A/C13A/N2A and C7B/N1B/C8B/C13B/N2B), respectively; Cg3 and Cg4 are the centroids of C8A-C13A and C8B-C13B phenyl rings, respectively].

Related literature top

For general background to and applications of benzimidazole derivatives, see: Denny et al. (1990); Evans et al. (1997); Grassmann et al. (2002); Göker et al. (2002); Seth et al. (2003). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995). For closely related benzimidazole structures, see: Arumugam et al. (2010a,b,c). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

A solution of ethyl-3-amino-4-(2-hydroxyethylamino) benzoate (0.5 g, 2.22 mmol) and sodium bisulfite adduct of p-methyl benzaldehyde (1.0 g, 4.46 mmol) in DMF was treated under microwave conditions at 403 K. The reaction mixture was then diluted in EtOAc (30 ml) and washed with H2O (30 ml). The organic layer was collected and dried over Na2SO4. The solvent was removed under reduced pressure to afford the crude product, which upon recrystallisation from EtOAc, revealed the title compound as colourless crystals.

Refinement top

Hydroxy H-atoms were located from the difference Fourier map and allowed to refine freely. The remaining H atoms were place in their calculated positions, with C–H = 0.93–0.97 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). The rotating group model was applied for the methyl groups. The highest residual electron density peak is 0.49 Å from N2B and the deepest hole is 0.85 Å from C8B.

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 (I) with 50% probability displacement ellipsoids for non-H atoms. Intramolecular hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Fit of molecule A (dashed lines) on molecule B (solid lines). H atoms have been omitted for clarity.
[Figure 3] Fig. 3. The crystal packing of (I), viewed down c axis, showing a two-molecule by two-molecule wide column along the a axis. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.
Ethyl 1-(2-hydroxyethyl)-2-p-tolyl-1H-benzimidazole-5-carboxylate top
Crystal data top
C19H20N2O3Z = 4
Mr = 324.37F(000) = 688
Triclinic, P1Dx = 1.324 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0400 (9) ÅCell parameters from 9690 reflections
b = 12.6806 (13) Åθ = 2.8–33.8°
c = 15.5504 (17) ŵ = 0.09 mm1
α = 74.170 (2)°T = 100 K
β = 74.360 (2)°Block, colourless
γ = 76.721 (2)°0.41 × 0.32 × 0.23 mm
V = 1627.9 (3) Å3
Data collection top
Bruker APEXII DUO CCD
diffractometer
10646 independent reflections
Radiation source: fine-focus sealed tube8773 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ϕ and ω scansθmax = 31.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1313
Tmin = 0.964, Tmax = 0.980k = 1818
30776 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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.1301P)2 + 0.1152P]
where P = (Fo2 + 2Fc2)/3
10646 reflections(Δ/σ)max < 0.001
445 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = 0.65 e Å3
Crystal data top
C19H20N2O3γ = 76.721 (2)°
Mr = 324.37V = 1627.9 (3) Å3
Triclinic, P1Z = 4
a = 9.0400 (9) ÅMo Kα radiation
b = 12.6806 (13) ŵ = 0.09 mm1
c = 15.5504 (17) ÅT = 100 K
α = 74.170 (2)°0.41 × 0.32 × 0.23 mm
β = 74.360 (2)°
Data collection top
Bruker APEXII DUO CCD
diffractometer
10646 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
8773 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.980Rint = 0.030
30776 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.60 e Å3
10646 reflectionsΔρmin = 0.65 e Å3
445 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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*/Ueq
O1A0.07593 (12)0.34205 (9)0.46417 (7)0.0276 (2)
O2A0.22621 (11)0.21688 (8)0.55131 (7)0.0214 (2)
O3A0.96752 (10)0.50727 (7)0.18794 (6)0.01475 (17)
N1A0.44922 (12)0.63318 (8)0.29752 (7)0.01358 (19)
N2A0.68064 (11)0.55873 (8)0.33553 (6)0.01221 (18)
C1A0.79520 (14)0.76316 (10)0.18103 (8)0.0153 (2)
H1AA0.87060.69990.17720.018*
C2A0.83043 (14)0.86714 (10)0.13230 (8)0.0170 (2)
H2AA0.93020.87230.09650.020*
C3A0.72088 (14)0.96366 (10)0.13554 (8)0.0164 (2)
C4A0.57258 (15)0.95372 (10)0.19112 (8)0.0172 (2)
H4AA0.49771.01720.19530.021*
C5A0.53556 (14)0.85052 (10)0.24015 (8)0.0161 (2)
H5AA0.43600.84560.27630.019*
C6A0.64640 (13)0.75385 (9)0.23574 (8)0.0132 (2)
C7A0.59444 (13)0.64791 (9)0.28754 (7)0.0127 (2)
C8A0.43877 (13)0.52957 (9)0.35614 (7)0.0123 (2)
C9A0.31274 (13)0.47294 (9)0.39126 (8)0.0139 (2)
H9AA0.21760.50290.37480.017*
C10A0.33376 (14)0.37013 (9)0.45175 (8)0.0141 (2)
C11A0.47717 (14)0.32492 (10)0.47744 (8)0.0148 (2)
H11A0.48690.25670.51910.018*
C12A0.60436 (14)0.37979 (9)0.44210 (8)0.0141 (2)
H12A0.69960.34980.45840.017*
C13A0.58203 (13)0.48226 (9)0.38085 (7)0.0122 (2)
C14A0.19800 (15)0.31049 (10)0.48803 (8)0.0168 (2)
C15A0.09808 (16)0.15392 (11)0.59046 (10)0.0240 (3)
H15A0.13830.07840.61900.029*
H15B0.05220.15060.54180.029*
C16A0.02486 (18)0.20524 (12)0.66008 (10)0.0256 (3)
H16A0.10420.15960.68670.038*
H16B0.07020.27800.63100.038*
H16C0.02090.21120.70720.038*
C17A0.84315 (13)0.53960 (9)0.34180 (8)0.0138 (2)
H17A0.85010.50880.40520.017*
H17B0.88060.61010.32210.017*
C18A0.94678 (13)0.46049 (10)0.28325 (8)0.0145 (2)
H18A1.04790.43870.29900.017*
H18B0.90110.39390.29750.017*
C19A0.75854 (17)1.07453 (11)0.07806 (10)0.0230 (3)
H19A0.86921.07220.06350.035*
H19B0.70821.13120.11160.035*
H19C0.72231.09090.02250.035*
O1B0.62907 (11)0.10394 (8)0.35690 (7)0.0212 (2)
O2B0.38151 (10)0.10387 (7)0.35342 (6)0.01744 (18)
O3B0.29192 (11)0.76162 (7)0.15387 (6)0.01769 (18)
N1B0.71022 (11)0.49118 (8)0.12914 (6)0.01173 (18)
N2B0.48235 (11)0.56326 (8)0.08697 (6)0.01134 (18)
C1B0.62243 (14)0.78327 (9)0.00981 (8)0.0148 (2)
H1BA0.52240.79900.04490.018*
C2B0.69291 (15)0.86841 (10)0.05266 (9)0.0184 (2)
H2BA0.63890.94100.05870.022*
C3B0.84224 (15)0.84821 (11)0.10662 (8)0.0196 (2)
C4B0.92369 (15)0.73979 (11)0.09289 (9)0.0192 (2)
H4BA1.02550.72500.12600.023*
C5B0.85548 (14)0.65327 (10)0.03060 (8)0.0158 (2)
H5BA0.91190.58140.02240.019*
C6B0.70215 (13)0.67365 (9)0.01996 (7)0.0123 (2)
C7B0.63190 (12)0.57798 (9)0.08024 (7)0.01131 (19)
C8B0.60714 (12)0.41630 (9)0.17018 (7)0.01138 (19)
C9B0.62468 (13)0.31246 (9)0.22990 (7)0.0124 (2)
H9BA0.71730.28210.24930.015*
C10B0.49860 (13)0.25547 (9)0.25962 (7)0.0128 (2)
C11B0.35857 (13)0.29980 (9)0.22970 (8)0.0138 (2)
H11B0.27790.25860.24960.017*
C12B0.33878 (13)0.40355 (9)0.17128 (8)0.0130 (2)
H12B0.24650.43370.15150.016*
C13B0.46462 (12)0.46028 (9)0.14371 (7)0.01133 (19)
C14B0.51372 (13)0.14745 (9)0.32729 (8)0.0141 (2)
C15B0.38024 (15)0.00252 (10)0.42410 (9)0.0191 (2)
H15C0.38120.01740.48190.023*
H15D0.47160.05180.40780.023*
C16B0.23432 (17)0.04128 (12)0.43262 (10)0.0253 (3)
H16D0.22660.10570.48220.038*
H16E0.23830.06110.37660.038*
H16F0.14510.01500.44450.038*
C17B0.35660 (13)0.63748 (9)0.04793 (8)0.0135 (2)
H17C0.30820.59610.02220.016*
H17D0.39900.69560.00140.016*
C18B0.23360 (13)0.69020 (10)0.11993 (8)0.0159 (2)
H18C0.14640.73220.09320.019*
H18D0.19530.63180.17060.019*
C19B0.9105 (2)0.94054 (13)0.17975 (10)0.0301 (3)
H19D1.02200.92150.19360.045*
H19E0.88011.00810.15820.045*
H19F0.87260.95080.23400.045*
H1OA0.875 (3)0.5068 (18)0.1692 (14)0.039 (6)*
H1OB0.328 (3)0.7248 (19)0.1973 (15)0.035 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0201 (5)0.0313 (5)0.0292 (5)0.0108 (4)0.0094 (4)0.0060 (4)
O2A0.0170 (4)0.0157 (4)0.0259 (5)0.0055 (3)0.0013 (3)0.0032 (3)
O3A0.0102 (4)0.0206 (4)0.0134 (4)0.0030 (3)0.0024 (3)0.0036 (3)
N1A0.0129 (4)0.0138 (4)0.0123 (4)0.0020 (3)0.0024 (3)0.0008 (3)
N2A0.0108 (4)0.0132 (4)0.0113 (4)0.0018 (3)0.0021 (3)0.0011 (3)
C1A0.0133 (5)0.0140 (5)0.0164 (5)0.0012 (4)0.0024 (4)0.0016 (4)
C2A0.0141 (5)0.0154 (5)0.0187 (5)0.0029 (4)0.0031 (4)0.0004 (4)
C3A0.0182 (5)0.0140 (5)0.0173 (5)0.0029 (4)0.0062 (4)0.0014 (4)
C4A0.0183 (5)0.0131 (5)0.0187 (5)0.0011 (4)0.0047 (4)0.0037 (4)
C5A0.0153 (5)0.0151 (5)0.0167 (5)0.0008 (4)0.0027 (4)0.0041 (4)
C6A0.0129 (5)0.0132 (5)0.0124 (5)0.0016 (4)0.0028 (4)0.0018 (4)
C7A0.0120 (5)0.0128 (5)0.0120 (4)0.0009 (4)0.0020 (4)0.0024 (4)
C8A0.0122 (5)0.0130 (5)0.0106 (4)0.0016 (4)0.0017 (4)0.0020 (4)
C9A0.0117 (5)0.0155 (5)0.0134 (5)0.0020 (4)0.0020 (4)0.0026 (4)
C10A0.0148 (5)0.0145 (5)0.0121 (5)0.0035 (4)0.0009 (4)0.0027 (4)
C11A0.0150 (5)0.0144 (5)0.0132 (5)0.0023 (4)0.0020 (4)0.0011 (4)
C12A0.0127 (5)0.0145 (5)0.0131 (5)0.0008 (4)0.0029 (4)0.0012 (4)
C13A0.0119 (5)0.0130 (5)0.0103 (4)0.0017 (4)0.0008 (3)0.0023 (4)
C14A0.0177 (5)0.0167 (5)0.0149 (5)0.0049 (4)0.0017 (4)0.0021 (4)
C15A0.0205 (6)0.0164 (5)0.0307 (7)0.0084 (4)0.0015 (5)0.0008 (5)
C16A0.0277 (7)0.0268 (6)0.0219 (6)0.0118 (5)0.0004 (5)0.0035 (5)
C17A0.0117 (5)0.0163 (5)0.0137 (5)0.0020 (4)0.0038 (4)0.0031 (4)
C18A0.0116 (5)0.0164 (5)0.0142 (5)0.0001 (4)0.0041 (4)0.0021 (4)
C19A0.0263 (7)0.0144 (5)0.0257 (6)0.0042 (5)0.0074 (5)0.0022 (5)
O1B0.0168 (4)0.0184 (4)0.0249 (5)0.0033 (3)0.0078 (4)0.0044 (3)
O2B0.0155 (4)0.0163 (4)0.0181 (4)0.0053 (3)0.0037 (3)0.0021 (3)
O3B0.0189 (4)0.0150 (4)0.0177 (4)0.0003 (3)0.0036 (3)0.0039 (3)
N1B0.0096 (4)0.0128 (4)0.0121 (4)0.0017 (3)0.0029 (3)0.0013 (3)
N2B0.0092 (4)0.0110 (4)0.0126 (4)0.0003 (3)0.0035 (3)0.0009 (3)
C1B0.0140 (5)0.0136 (5)0.0165 (5)0.0008 (4)0.0053 (4)0.0023 (4)
C2B0.0203 (6)0.0148 (5)0.0206 (6)0.0038 (4)0.0089 (4)0.0003 (4)
C3B0.0213 (6)0.0207 (6)0.0174 (5)0.0093 (4)0.0068 (4)0.0021 (4)
C4B0.0142 (5)0.0233 (6)0.0176 (5)0.0059 (4)0.0003 (4)0.0016 (4)
C5B0.0126 (5)0.0171 (5)0.0161 (5)0.0023 (4)0.0023 (4)0.0021 (4)
C6B0.0110 (5)0.0138 (5)0.0117 (4)0.0021 (4)0.0038 (4)0.0011 (4)
C7B0.0091 (4)0.0129 (5)0.0116 (4)0.0013 (3)0.0022 (3)0.0028 (4)
C8B0.0092 (4)0.0137 (5)0.0111 (4)0.0015 (3)0.0020 (3)0.0031 (4)
C9B0.0098 (4)0.0145 (5)0.0124 (5)0.0004 (3)0.0031 (4)0.0030 (4)
C10B0.0121 (5)0.0130 (5)0.0121 (5)0.0013 (4)0.0020 (4)0.0024 (4)
C11B0.0120 (5)0.0145 (5)0.0143 (5)0.0027 (4)0.0027 (4)0.0020 (4)
C12B0.0100 (5)0.0151 (5)0.0137 (5)0.0019 (4)0.0034 (4)0.0027 (4)
C13B0.0100 (4)0.0123 (4)0.0113 (4)0.0011 (3)0.0028 (3)0.0023 (4)
C14B0.0135 (5)0.0144 (5)0.0137 (5)0.0027 (4)0.0021 (4)0.0025 (4)
C15B0.0195 (6)0.0163 (5)0.0188 (5)0.0061 (4)0.0048 (4)0.0033 (4)
C16B0.0210 (6)0.0237 (6)0.0298 (7)0.0086 (5)0.0022 (5)0.0032 (5)
C17B0.0108 (5)0.0134 (5)0.0157 (5)0.0008 (4)0.0063 (4)0.0013 (4)
C18B0.0107 (5)0.0154 (5)0.0196 (5)0.0004 (4)0.0032 (4)0.0028 (4)
C19B0.0342 (8)0.0284 (7)0.0255 (7)0.0173 (6)0.0068 (6)0.0079 (5)
Geometric parameters (Å, º) top
O1A—C14A1.2051 (17)O1B—C14B1.2082 (15)
O2A—C14A1.3422 (15)O2B—C14B1.3483 (14)
O2A—C15A1.4591 (15)O2B—C15B1.4454 (14)
O3A—C18A1.4160 (14)O3B—C18B1.4166 (15)
O3A—H1OA0.96 (2)O3B—H1OB0.81 (2)
N1A—C7A1.3302 (15)N1B—C7B1.3291 (14)
N1A—C8A1.3868 (14)N1B—C8B1.3902 (13)
N2A—C7A1.3752 (15)N2B—C13B1.3787 (14)
N2A—C13A1.3846 (14)N2B—C7B1.3793 (14)
N2A—C17A1.4586 (15)N2B—C17B1.4545 (14)
C1A—C2A1.3899 (16)C1B—C2B1.3875 (16)
C1A—C6A1.3959 (16)C1B—C6B1.3993 (16)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.3896 (17)C2B—C3B1.3928 (18)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.3978 (17)C3B—C4B1.3919 (19)
C3A—C19A1.5038 (17)C3B—C19B1.5072 (18)
C4A—C5A1.3875 (16)C4B—C5B1.3896 (16)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.3985 (16)C5B—C6B1.4017 (16)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.4729 (15)C6B—C7B1.4718 (15)
C8A—C9A1.3923 (15)C8B—C9B1.3919 (15)
C8A—C13A1.4037 (16)C8B—C13B1.4039 (15)
C9A—C10A1.3906 (16)C9B—C10B1.3954 (15)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—C11A1.4078 (17)C10B—C11B1.4082 (16)
C10A—C14A1.4889 (16)C10B—C14B1.4858 (16)
C11A—C12A1.3879 (15)C11B—C12B1.3840 (16)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.3945 (16)C12B—C13B1.3929 (14)
C12A—H12A0.9300C12B—H12B0.9300
C15A—C16A1.495 (2)C15B—C16B1.5060 (18)
C15A—H15A0.9700C15B—H15C0.9700
C15A—H15B0.9700C15B—H15D0.9700
C16A—H16A0.9600C16B—H16D0.9600
C16A—H16B0.9600C16B—H16E0.9600
C16A—H16C0.9600C16B—H16F0.9600
C17A—C18A1.5230 (16)C17B—C18B1.5272 (16)
C17A—H17A0.9700C17B—H17C0.9700
C17A—H17B0.9700C17B—H17D0.9700
C18A—H18A0.9700C18B—H18C0.9700
C18A—H18B0.9700C18B—H18D0.9700
C19A—H19A0.9600C19B—H19D0.9600
C19A—H19B0.9600C19B—H19E0.9600
C19A—H19C0.9600C19B—H19F0.9600
C14A—O2A—C15A115.51 (11)C14B—O2B—C15B116.22 (10)
C18A—O3A—H1OA108.5 (13)C18B—O3B—H1OB108.2 (15)
C7A—N1A—C8A105.16 (10)C7B—N1B—C8B105.51 (9)
C7A—N2A—C13A106.47 (9)C13B—N2B—C7B107.03 (9)
C7A—N2A—C17A130.53 (9)C13B—N2B—C17B122.50 (9)
C13A—N2A—C17A123.00 (10)C7B—N2B—C17B130.43 (10)
C2A—C1A—C6A119.88 (11)C2B—C1B—C6B119.85 (11)
C2A—C1A—H1AA120.1C2B—C1B—H1BA120.1
C6A—C1A—H1AA120.1C6B—C1B—H1BA120.1
C3A—C2A—C1A121.93 (11)C1B—C2B—C3B121.82 (12)
C3A—C2A—H2AA119.0C1B—C2B—H2BA119.1
C1A—C2A—H2AA119.0C3B—C2B—H2BA119.1
C2A—C3A—C4A117.82 (11)C4B—C3B—C2B117.94 (11)
C2A—C3A—C19A121.07 (11)C4B—C3B—C19B121.33 (12)
C4A—C3A—C19A121.05 (11)C2B—C3B—C19B120.70 (13)
C5A—C4A—C3A120.93 (11)C5B—C4B—C3B121.13 (11)
C5A—C4A—H4AA119.5C5B—C4B—H4BA119.4
C3A—C4A—H4AA119.5C3B—C4B—H4BA119.4
C4A—C5A—C6A120.73 (11)C4B—C5B—C6B120.40 (11)
C4A—C5A—H5AA119.6C4B—C5B—H5BA119.8
C6A—C5A—H5AA119.6C6B—C5B—H5BA119.8
C1A—C6A—C5A118.69 (10)C1B—C6B—C5B118.70 (10)
C1A—C6A—C7A124.55 (10)C1B—C6B—C7B123.14 (10)
C5A—C6A—C7A116.72 (10)C5B—C6B—C7B118.15 (10)
N1A—C7A—N2A112.70 (10)N1B—C7B—N2B112.04 (9)
N1A—C7A—C6A121.20 (10)N1B—C7B—C6B123.42 (10)
N2A—C7A—C6A125.93 (10)N2B—C7B—C6B124.34 (10)
N1A—C8A—C9A129.96 (11)N1B—C8B—C9B130.89 (10)
N1A—C8A—C13A109.82 (10)N1B—C8B—C13B109.62 (10)
C9A—C8A—C13A120.21 (10)C9B—C8B—C13B119.49 (10)
C10A—C9A—C8A117.82 (11)C8B—C9B—C10B117.73 (10)
C10A—C9A—H9AA121.1C8B—C9B—H9BA121.1
C8A—C9A—H9AA121.1C10B—C9B—H9BA121.1
C9A—C10A—C11A121.28 (11)C9B—C10B—C11B121.69 (10)
C9A—C10A—C14A117.03 (11)C9B—C10B—C14B117.90 (10)
C11A—C10A—C14A121.70 (11)C11B—C10B—C14B120.37 (10)
C12A—C11A—C10A121.52 (11)C12B—C11B—C10B121.18 (10)
C12A—C11A—H11A119.2C12B—C11B—H11B119.4
C10A—C11A—H11A119.2C10B—C11B—H11B119.4
C11A—C12A—C13A116.56 (11)C11B—C12B—C13B116.38 (10)
C11A—C12A—H12A121.7C11B—C12B—H12B121.8
C13A—C12A—H12A121.7C13B—C12B—H12B121.8
N2A—C13A—C12A131.53 (11)N2B—C13B—C12B130.72 (10)
N2A—C13A—C8A105.85 (10)N2B—C13B—C8B105.80 (9)
C12A—C13A—C8A122.58 (10)C12B—C13B—C8B123.46 (10)
O1A—C14A—O2A123.30 (11)O1B—C14B—O2B123.54 (11)
O1A—C14A—C10A124.42 (12)O1B—C14B—C10B124.61 (11)
O2A—C14A—C10A112.29 (11)O2B—C14B—C10B111.84 (10)
O2A—C15A—C16A111.79 (11)O2B—C15B—C16B107.68 (11)
O2A—C15A—H15A109.3O2B—C15B—H15C110.2
C16A—C15A—H15A109.3C16B—C15B—H15C110.2
O2A—C15A—H15B109.3O2B—C15B—H15D110.2
C16A—C15A—H15B109.3C16B—C15B—H15D110.2
H15A—C15A—H15B107.9H15C—C15B—H15D108.5
C15A—C16A—H16A109.5C15B—C16B—H16D109.5
C15A—C16A—H16B109.5C15B—C16B—H16E109.5
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
C15A—C16A—H16C109.5C15B—C16B—H16F109.5
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
N2A—C17A—C18A112.15 (9)N2B—C17B—C18B111.50 (9)
N2A—C17A—H17A109.2N2B—C17B—H17C109.3
C18A—C17A—H17A109.2C18B—C17B—H17C109.3
N2A—C17A—H17B109.2N2B—C17B—H17D109.3
C18A—C17A—H17B109.2C18B—C17B—H17D109.3
H17A—C17A—H17B107.9H17C—C17B—H17D108.0
O3A—C18A—C17A113.28 (9)O3B—C18B—C17B112.66 (9)
O3A—C18A—H18A108.9O3B—C18B—H18C109.1
C17A—C18A—H18A108.9C17B—C18B—H18C109.1
O3A—C18A—H18B108.9O3B—C18B—H18D109.1
C17A—C18A—H18B108.9C17B—C18B—H18D109.1
H18A—C18A—H18B107.7H18C—C18B—H18D107.8
C3A—C19A—H19A109.5C3B—C19B—H19D109.5
C3A—C19A—H19B109.5C3B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C3A—C19A—H19C109.5C3B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
C6A—C1A—C2A—C3A0.49 (18)C6B—C1B—C2B—C3B0.21 (18)
C1A—C2A—C3A—C4A1.04 (18)C1B—C2B—C3B—C4B3.33 (18)
C1A—C2A—C3A—C19A176.41 (11)C1B—C2B—C3B—C19B174.55 (12)
C2A—C3A—C4A—C5A1.06 (18)C2B—C3B—C4B—C5B3.20 (19)
C19A—C3A—C4A—C5A176.39 (11)C19B—C3B—C4B—C5B174.67 (12)
C3A—C4A—C5A—C6A0.55 (18)C3B—C4B—C5B—C6B0.03 (19)
C2A—C1A—C6A—C5A0.06 (17)C2B—C1B—C6B—C5B3.06 (17)
C2A—C1A—C6A—C7A177.64 (11)C2B—C1B—C6B—C7B175.93 (11)
C4A—C5A—C6A—C1A0.03 (17)C4B—C5B—C6B—C1B3.18 (17)
C4A—C5A—C6A—C7A177.85 (11)C4B—C5B—C6B—C7B175.86 (11)
C8A—N1A—C7A—N2A0.84 (12)C8B—N1B—C7B—N2B0.29 (12)
C8A—N1A—C7A—C6A174.66 (9)C8B—N1B—C7B—C6B175.30 (10)
C13A—N2A—C7A—N1A1.15 (12)C13B—N2B—C7B—N1B0.12 (12)
C17A—N2A—C7A—N1A178.46 (10)C17B—N2B—C7B—N1B177.66 (10)
C13A—N2A—C7A—C6A174.10 (10)C13B—N2B—C7B—C6B174.83 (10)
C17A—N2A—C7A—C6A6.29 (18)C17B—N2B—C7B—C6B7.39 (17)
C1A—C6A—C7A—N1A144.30 (12)C1B—C6B—C7B—N1B142.71 (11)
C5A—C6A—C7A—N1A33.45 (15)C5B—C6B—C7B—N1B38.29 (15)
C1A—C6A—C7A—N2A40.83 (17)C1B—C6B—C7B—N2B42.90 (16)
C5A—C6A—C7A—N2A141.43 (11)C5B—C6B—C7B—N2B136.10 (11)
C7A—N1A—C8A—C9A178.75 (11)C7B—N1B—C8B—C9B178.72 (11)
C7A—N1A—C8A—C13A0.21 (12)C7B—N1B—C8B—C13B0.59 (12)
N1A—C8A—C9A—C10A178.00 (10)N1B—C8B—C9B—C10B179.58 (10)
C13A—C8A—C9A—C10A0.88 (16)C13B—C8B—C9B—C10B1.16 (15)
C8A—C9A—C10A—C11A0.54 (16)C8B—C9B—C10B—C11B0.93 (16)
C8A—C9A—C10A—C14A179.57 (10)C8B—C9B—C10B—C14B176.73 (9)
C9A—C10A—C11A—C12A1.38 (17)C9B—C10B—C11B—C12B1.80 (17)
C14A—C10A—C11A—C12A178.74 (10)C14B—C10B—C11B—C12B175.80 (10)
C10A—C11A—C12A—C13A0.71 (16)C10B—C11B—C12B—C13B0.48 (16)
C7A—N2A—C13A—C12A176.79 (11)C7B—N2B—C13B—C12B178.09 (11)
C17A—N2A—C13A—C12A3.56 (18)C17B—N2B—C13B—C12B3.91 (17)
C7A—N2A—C13A—C8A0.93 (11)C7B—N2B—C13B—C8B0.47 (11)
C17A—N2A—C13A—C8A178.72 (9)C17B—N2B—C13B—C8B177.53 (9)
C11A—C12A—C13A—N2A178.14 (11)C11B—C12B—C13B—N2B179.96 (11)
C11A—C12A—C13A—C8A0.75 (16)C11B—C12B—C13B—C8B1.69 (16)
N1A—C8A—C13A—N2A0.46 (12)N1B—C8B—C13B—N2B0.67 (12)
C9A—C8A—C13A—N2A179.55 (9)C9B—C8B—C13B—N2B178.74 (9)
N1A—C8A—C13A—C12A177.51 (10)N1B—C8B—C13B—C12B178.03 (9)
C9A—C8A—C13A—C12A1.57 (17)C9B—C8B—C13B—C12B2.56 (16)
C15A—O2A—C14A—O1A0.05 (18)C15B—O2B—C14B—O1B3.17 (17)
C15A—O2A—C14A—C10A179.75 (10)C15B—O2B—C14B—C10B175.76 (9)
C9A—C10A—C14A—O1A4.82 (18)C9B—C10B—C14B—O1B1.86 (17)
C11A—C10A—C14A—O1A175.29 (12)C11B—C10B—C14B—O1B179.55 (11)
C9A—C10A—C14A—O2A174.87 (10)C9B—C10B—C14B—O2B177.06 (9)
C11A—C10A—C14A—O2A5.02 (16)C11B—C10B—C14B—O2B0.64 (15)
C14A—O2A—C15A—C16A77.41 (15)C14B—O2B—C15B—C16B171.37 (10)
C7A—N2A—C17A—C18A102.64 (13)C13B—N2B—C17B—C18B73.62 (13)
C13A—N2A—C17A—C18A76.92 (13)C7B—N2B—C17B—C18B103.86 (13)
N2A—C17A—C18A—O3A70.06 (12)N2B—C17B—C18B—O3B65.15 (12)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the N1B/C7B/N2B/C8B/C13B 4,5-dihydro imidazole ring.
D—H···AD—HH···AD···AD—H···A
O3A—H1OA···N1B0.96 (3)1.83 (3)2.7847 (14)173 (2)
O3B—H1OB···N1A0.81 (2)2.08 (2)2.8859 (15)172 (3)
C1A—H1AA···O3A0.932.373.2473 (16)156
C1B—H1BA···O3B0.932.363.2331 (16)157
C12B—H12B···O3Ai0.932.453.2788 (16)149
C15B—H15C···O1Bii0.972.553.2889 (17)133
C18A—H18A···O1Aiii0.972.583.1928 (16)121
C17B—H17C···Cg1iv0.972.703.4194 (13)131
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z+1; (iii) x+1, y, z; (iv) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC19H20N2O3
Mr324.37
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)9.0400 (9), 12.6806 (13), 15.5504 (17)
α, β, γ (°)74.170 (2), 74.360 (2), 76.721 (2)
V3)1627.9 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.41 × 0.32 × 0.23
Data collection
DiffractometerBruker APEXII DUO CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.964, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
30776, 10646, 8773
Rint0.030
(sin θ/λ)max1)0.735
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.194, 1.13
No. of reflections10646
No. of parameters445
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.60, 0.65

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

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the N1B/C7B/N2B/C8B/C13B 4,5-dihydro imidazole ring.
D—H···AD—HH···AD···AD—H···A
O3A—H1OA···N1B0.96 (3)1.83 (3)2.7847 (14)173 (2)
O3B—H1OB···N1A0.81 (2)2.08 (2)2.8859 (15)172 (3)
C1A—H1AA···O3A0.932.373.2473 (16)156
C1B—H1BA···O3B0.932.363.2331 (16)157
C12B—H12B···O3Ai0.932.453.2788 (16)149
C15B—H15C···O1Bii0.972.553.2889 (17)133
C18A—H18A···O1Aiii0.972.583.1928 (16)121
C17B—H17C···Cg1iv0.972.703.4194 (13)131
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z+1; (iii) x+1, y, z; (iv) x+1, y+1, z.
 

Footnotes

Additional correspondence author, e-mail: aisyah@usm.my.

§Thomson Reuters ResearcherID: C-7576-2009.

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

NA, ASAR and HAW acknowledge Universiti Sains Malaysia (USM) for funding the synthetic chemistry work under the USM Research University Grant (No. 1001/PFARMASI/815026) and the Ministry of Science, Technology and Innovations (MOSTI) Grant (No. 304/PFARMASI/650512/I121). NA also thanks USM for the award of a postdoctoral fellowship. HKF and JHG thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

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Volume 66| Part 7| July 2010| Pages o1590-o1591
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