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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1214–o1215.
Published online 2010 April 30. doi:  10.1107/S1600536810015242
PMCID: PMC2979236

Ethyl 1-sec-butyl-2-p-tolyl-1H-benzimidazole-5-carboxyl­ate

Abstract

In the title compound, C21H24N2O2, the butyl group is disordered over two orientations with refined site occupancies of 0.883 (3) and 0.117 (3). The dihedral angle between the mean plane of benzimidazole ring system and the benzene ring is 39.32 (4)° and the dihedral angle between the mean plane of carboxyl­ate group and the benzimidazole ring system is 6.87 (5)°. A weak intra­molecular C—H(...)π inter­action may have some influence on the conformation of the mol­ecule. In the crystal structure, mol­ecules are linked into infinite chains along the b axis by weak inter­molecular C—H(...)O hydrogen bonds.

Related literature

For background information on benzimidazole derivatives, their biological activity and medical applications, see: Richter (1997 [triangle]); Can-Eke et al. (1998 [triangle]); Evans et al. (1997 [triangle]); Garuti et al. (2000 [triangle]); Sondhi et al. (2005 [triangle]). For the synthesis of the title compound and related structures, see: Arumugam et al. (2010a [triangle],b [triangle],c [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

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Object name is e-66-o1214-scheme1.jpg

Experimental

Crystal data

  • C21H24N2O2
  • M r = 336.42
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1214-efi1.jpg
  • a = 10.6093 (7) Å
  • b = 12.5617 (9) Å
  • c = 13.6025 (10) Å
  • β = 96.412 (2)°
  • V = 1801.5 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 K
  • 0.46 × 0.29 × 0.24 mm

Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.964, T max = 0.981
  • 31247 measured reflections
  • 8425 independent reflections
  • 6598 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.177
  • S = 1.08
  • 8425 reflections
  • 249 parameters
  • H-atom parameters constrained
  • Δρmax = 0.58 e Å−3
  • Δρmin = −0.35 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015242/lh5024sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015242/lh5024Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

NA, ASAR and HO are grateful to Universiti Sains Malaysia (USM) for funding the synthetic chemistry work under the USM Research University Grant (1001/PFARMASI/815026). NA thanks USM for the award of a postdoctoral fellowship. HKF and CSY thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). CSY also thanks USM for the award of a USM fellowship.

supplementary crystallographic information

Comment

Benzimidazoles are important heterocyclic compounds from the view point of their biological activities. Substituted benzimidazole derivatives have diverse therapeutic applications as they exhibit antiulcerative (Richter, 1997), antioxidant (Can-Eke et al., 1998), anti-HIV-1 (Evans et al., 1997), antiproliferative (Garuti et al., 2000) and antikinase (Sondhi et al., 2005) activities. In view of their importance, the crystal structure determination of the title compound was carried out and the results are presented herein.

The geometric parameters of the title compound (Fig. 1) are comparable to those closely related structures (Arumugam et al., 2010a,b,c). The butyl group is disordered over two positions with refined site-occupancies of 0.883 (3) and 0.117 (3). The dihedral angle between the mean plane of benzimidazole ring system (C7/N1/C8–C13/N2) and the benzene ring (C1–C6) is 39.32 (4)°. The mean plane of carboxylate group (O1/O2/C14–C16) is slightly twisted from the mean plane of benzimidazole ring system with a dihedral angle of 6.87 (5)°. In the crystal structure, the molecules are linked into infinite one-dimensional chains along b axis by intermolecular C12—H12A···O1i hydrogen bonds (Fig. 2, Table 1). A weak intramolecular C20—H20C···Cg1 interaction may have some influence on the conformation of the molecule (Table 1).

Experimental

The title compound was synthesised using the previous procedures (Arumugam et al., 2010a,b,c) and recrystallized from EtOAc by slow evaporation technique.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93–0.98 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). The rotating group model was applied for the methyl groups. The minor disorder component is refined isotropically.

Figures

Fig. 1.
The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids for non-H atoms. All disorder components are shown.
Fig. 2.
The crystal packing of the title compound, viewed along the a axis, showing one-dimensional chains along the b axis. Intermolecular hydrogen bonds are shown as dashed lines. Only the major disorder component is shown.

Crystal data

C21H24N2O2F(000) = 720
Mr = 336.42Dx = 1.240 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9348 reflections
a = 10.6093 (7) Åθ = 2.5–35.7°
b = 12.5617 (9) ŵ = 0.08 mm1
c = 13.6025 (10) ÅT = 100 K
β = 96.412 (2)°Block, colourless
V = 1801.5 (2) Å30.46 × 0.29 × 0.24 mm
Z = 4

Data collection

Bruker APEXII DUO CCD area-detector diffractometer8425 independent reflections
Radiation source: fine-focus sealed tube6598 reflections with I > 2σ(I)
graphiteRint = 0.050
[var phi] and ω scansθmax = 35.9°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −17→17
Tmin = 0.964, Tmax = 0.981k = −20→18
31247 measured reflectionsl = −22→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0965P)2 + 0.2974P] where P = (Fo2 + 2Fc2)/3
8425 reflections(Δ/σ)max = 0.001
249 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = −0.35 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
O10.49342 (7)0.02746 (7)0.17217 (6)0.02380 (16)
O20.65726 (7)−0.02944 (6)0.09409 (6)0.02268 (16)
N10.97240 (7)0.27803 (6)0.12066 (6)0.01543 (14)
N20.88175 (7)0.41780 (6)0.19145 (6)0.01655 (14)
C11.08554 (9)0.54848 (8)0.10257 (7)0.01777 (16)
H1A1.00630.58100.09550.021*
C21.19164 (9)0.60526 (8)0.08166 (7)0.01913 (17)
H2A1.18260.67570.06110.023*
C31.31155 (9)0.55829 (8)0.09096 (7)0.01821 (16)
C41.32288 (9)0.45317 (8)0.12279 (8)0.02007 (17)
H4A1.40230.42090.12990.024*
C51.21734 (8)0.39545 (8)0.14411 (7)0.01823 (16)
H5A1.22670.32510.16510.022*
C61.09738 (8)0.44266 (7)0.13421 (7)0.01533 (15)
C70.98590 (8)0.37775 (7)0.15004 (7)0.01501 (15)
C80.85266 (8)0.24973 (7)0.14314 (6)0.01444 (14)
C90.78890 (8)0.15330 (7)0.12648 (7)0.01558 (15)
H9A0.82620.09640.09690.019*
C100.66749 (8)0.14490 (7)0.15547 (7)0.01544 (15)
C110.61067 (8)0.23144 (8)0.19943 (7)0.01795 (16)
H11A0.52930.22350.21760.022*
C120.67222 (9)0.32803 (8)0.21644 (7)0.01830 (16)
H12A0.63440.38480.24570.022*
C130.79460 (8)0.33574 (7)0.18720 (7)0.01546 (15)
C140.59579 (9)0.04345 (8)0.14279 (7)0.01746 (16)
C150.59689 (11)−0.13214 (8)0.07980 (9)0.0248 (2)
H15A0.5092−0.12390.05190.030*
H15B0.5987−0.16940.14240.030*
C160.67033 (12)−0.19304 (10)0.00983 (10)0.0309 (2)
H16A0.6344−0.2628−0.00070.046*
H16B0.7572−0.19920.03770.046*
H16C0.6662−0.1560−0.05220.046*
C170.88130 (11)0.51250 (9)0.25531 (10)0.0177 (2)0.883 (3)
H17A0.96320.54810.25350.021*0.883 (3)
C180.77857 (12)0.59232 (10)0.21723 (12)0.0295 (3)0.883 (3)
H18A0.78300.60540.14820.044*0.883 (3)
H18B0.79150.65780.25330.044*0.883 (3)
H18C0.69670.56390.22630.044*0.883 (3)
C190.87392 (12)0.47809 (11)0.36205 (9)0.0252 (3)0.883 (3)
H19A0.88520.53990.40480.030*0.883 (3)
H19B0.79040.44890.36780.030*0.883 (3)
C200.97390 (13)0.39537 (13)0.39635 (9)0.0283 (3)0.883 (3)
H20A0.96960.37940.46490.042*0.883 (3)
H20B1.05650.42280.38800.042*0.883 (3)
H20C0.95880.33170.35780.042*0.883 (3)
C17B0.9123 (10)0.4910 (8)0.2883 (8)0.0205 (17)*0.117 (3)
H17B0.99140.52910.28100.025*0.117 (3)
C18B0.9279 (12)0.4407 (10)0.3838 (8)0.028 (2)*0.117 (3)
H18D0.93590.49420.43450.042*0.117 (3)
H18E1.00280.39730.38950.042*0.117 (3)
H18F0.85530.39700.39120.042*0.117 (3)
C19B0.8068 (10)0.5725 (9)0.2776 (8)0.028 (2)*0.117 (3)
H19C0.82370.62490.32980.034*0.117 (3)
H19D0.72810.53700.28780.034*0.117 (3)
C20B0.7858 (14)0.6360 (12)0.1703 (11)0.041 (3)*0.117 (3)
H20D0.72880.69460.17510.061*0.117 (3)
H20E0.75070.58790.11960.061*0.117 (3)
H20F0.86590.66230.15410.061*0.117 (3)
C211.42509 (11)0.62003 (10)0.06554 (8)0.0258 (2)
H21A1.50010.59360.10380.039*
H21B1.41420.69400.08020.039*
H21C1.43340.6119−0.00360.039*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0180 (3)0.0222 (4)0.0325 (4)−0.0070 (2)0.0084 (3)−0.0006 (3)
O20.0226 (3)0.0155 (3)0.0316 (4)−0.0089 (2)0.0100 (3)−0.0062 (3)
N10.0142 (3)0.0130 (3)0.0200 (3)−0.0026 (2)0.0059 (2)−0.0017 (2)
N20.0157 (3)0.0132 (3)0.0217 (3)−0.0031 (2)0.0066 (3)−0.0045 (2)
C10.0181 (4)0.0147 (4)0.0207 (4)−0.0026 (3)0.0031 (3)0.0002 (3)
C20.0231 (4)0.0151 (4)0.0195 (4)−0.0057 (3)0.0035 (3)0.0004 (3)
C30.0187 (4)0.0190 (4)0.0175 (4)−0.0073 (3)0.0046 (3)−0.0017 (3)
C40.0163 (4)0.0195 (4)0.0252 (4)−0.0035 (3)0.0057 (3)0.0000 (3)
C50.0160 (3)0.0152 (4)0.0242 (4)−0.0019 (3)0.0056 (3)0.0004 (3)
C60.0153 (3)0.0138 (4)0.0174 (3)−0.0034 (3)0.0044 (3)−0.0016 (3)
C70.0141 (3)0.0135 (4)0.0181 (3)−0.0025 (2)0.0047 (3)−0.0014 (3)
C80.0139 (3)0.0123 (3)0.0178 (3)−0.0025 (2)0.0045 (3)−0.0015 (3)
C90.0155 (3)0.0127 (3)0.0192 (4)−0.0028 (3)0.0048 (3)−0.0018 (3)
C100.0153 (3)0.0139 (4)0.0175 (3)−0.0037 (3)0.0037 (3)−0.0001 (3)
C110.0145 (3)0.0184 (4)0.0217 (4)−0.0024 (3)0.0056 (3)−0.0012 (3)
C120.0153 (3)0.0168 (4)0.0238 (4)−0.0016 (3)0.0068 (3)−0.0038 (3)
C130.0142 (3)0.0135 (4)0.0193 (4)−0.0026 (3)0.0047 (3)−0.0028 (3)
C140.0166 (3)0.0162 (4)0.0197 (4)−0.0044 (3)0.0027 (3)0.0008 (3)
C150.0265 (5)0.0175 (4)0.0314 (5)−0.0108 (3)0.0076 (4)−0.0043 (4)
C160.0303 (5)0.0212 (5)0.0426 (6)−0.0081 (4)0.0110 (5)−0.0081 (4)
C170.0177 (4)0.0137 (4)0.0224 (5)−0.0019 (3)0.0046 (4)−0.0060 (4)
C180.0230 (5)0.0171 (5)0.0492 (9)0.0041 (4)0.0076 (5)−0.0052 (5)
C190.0232 (5)0.0321 (7)0.0213 (5)−0.0070 (5)0.0070 (4)−0.0101 (4)
C200.0289 (6)0.0361 (7)0.0195 (5)−0.0105 (5)0.0007 (4)0.0019 (4)
C210.0246 (4)0.0261 (5)0.0280 (5)−0.0124 (4)0.0090 (4)−0.0016 (4)

Geometric parameters (Å, °)

O1—C141.2151 (11)C15—H15A0.9700
O2—C141.3412 (12)C15—H15B0.9700
O2—C151.4438 (12)C16—H16A0.9600
N1—C71.3178 (12)C16—H16B0.9600
N1—C81.3858 (11)C16—H16C0.9600
N2—C131.3817 (11)C17—C191.5253 (18)
N2—C71.3895 (11)C17—C181.5281 (19)
N2—C171.4733 (13)C17—H17A0.9800
N2—C17B1.609 (10)C18—H18A0.9600
C1—C21.3886 (13)C18—H18B0.9600
C1—C61.3985 (13)C18—H18C0.9600
C1—H1A0.9300C19—C201.521 (2)
C2—C31.3952 (14)C19—H19A0.9700
C2—H2A0.9300C19—H19B0.9700
C3—C41.3907 (14)C20—H20A0.9600
C3—C211.5051 (13)C20—H20B0.9600
C4—C51.3914 (13)C20—H20C0.9600
C4—H4A0.9300C17B—C18B1.438 (16)
C5—C61.3969 (13)C17B—C19B1.512 (15)
C5—H5A0.9300C17B—H17B0.9800
C6—C71.4720 (12)C18B—H18D0.9600
C8—C91.3935 (12)C18B—H18E0.9600
C8—C131.4101 (12)C18B—H18F0.9600
C9—C101.3926 (12)C19B—C20B1.656 (19)
C9—H9A0.9300C19B—H19C0.9700
C10—C111.4083 (13)C19B—H19D0.9700
C10—C141.4842 (13)C20B—H20D0.9600
C11—C121.3851 (13)C20B—H20E0.9600
C11—H11A0.9300C20B—H20F0.9600
C12—C131.4031 (12)C21—H21A0.9600
C12—H12A0.9300C21—H21B0.9600
C15—C161.5047 (17)C21—H21C0.9600
C14—O2—C15116.33 (8)O2—C15—H15B110.4
C7—N1—C8104.38 (7)C16—C15—H15B110.4
C13—N2—C7105.76 (7)H15A—C15—H15B108.6
C13—N2—C17125.52 (8)C15—C16—H16A109.5
C7—N2—C17125.91 (8)C15—C16—H16B109.5
C13—N2—C17B122.2 (4)H16A—C16—H16B109.5
C7—N2—C17B116.2 (4)C15—C16—H16C109.5
C2—C1—C6120.28 (9)H16A—C16—H16C109.5
C2—C1—H1A119.9H16B—C16—H16C109.5
C6—C1—H1A119.9N2—C17—C19109.65 (10)
C1—C2—C3121.07 (9)N2—C17—C18112.27 (11)
C1—C2—H2A119.5C19—C17—C18113.46 (10)
C3—C2—H2A119.5N2—C17—H17A107.0
C4—C3—C2118.42 (8)C19—C17—H17A107.0
C4—C3—C21121.15 (9)C18—C17—H17A107.0
C2—C3—C21120.42 (10)C20—C19—C17112.18 (10)
C3—C4—C5121.07 (9)C20—C19—H19A109.2
C3—C4—H4A119.5C17—C19—H19A109.2
C5—C4—H4A119.5C20—C19—H19B109.2
C4—C5—C6120.29 (9)C17—C19—H19B109.2
C4—C5—H5A119.9H19A—C19—H19B107.9
C6—C5—H5A119.9C18B—C17B—C19B113.2 (9)
C5—C6—C1118.86 (8)C18B—C17B—N2118.7 (8)
C5—C6—C7119.27 (8)C19B—C17B—N2103.2 (8)
C1—C6—C7121.71 (8)C18B—C17B—H17B107.0
N1—C7—N2113.75 (7)C19B—C17B—H17B107.0
N1—C7—C6122.96 (8)N2—C17B—H17B107.0
N2—C7—C6123.17 (8)C17B—C18B—H18D109.5
N1—C8—C9128.86 (8)C17B—C18B—H18E109.5
N1—C8—C13110.60 (7)H18D—C18B—H18E109.5
C9—C8—C13120.53 (8)C17B—C18B—H18F109.5
C10—C9—C8117.86 (8)H18D—C18B—H18F109.5
C10—C9—H9A121.1H18E—C18B—H18F109.5
C8—C9—H9A121.1C17B—C19B—C20B115.8 (9)
C9—C10—C11121.00 (8)C17B—C19B—H19C108.3
C9—C10—C14120.69 (8)C20B—C19B—H19C108.3
C11—C10—C14118.29 (8)C17B—C19B—H19D108.3
C12—C11—C10122.07 (8)C20B—C19B—H19D108.3
C12—C11—H11A119.0H19C—C19B—H19D107.4
C10—C11—H11A119.0C19B—C20B—H20D109.5
C11—C12—C13116.55 (8)C19B—C20B—H20E109.5
C11—C12—H12A121.7H20D—C20B—H20E109.5
C13—C12—H12A121.7C19B—C20B—H20F109.5
N2—C13—C12132.51 (8)H20D—C20B—H20F109.5
N2—C13—C8105.51 (7)H20E—C20B—H20F109.5
C12—C13—C8121.98 (8)C3—C21—H21A109.5
O1—C14—O2123.46 (9)C3—C21—H21B109.5
O1—C14—C10124.68 (9)H21A—C21—H21B109.5
O2—C14—C10111.86 (8)C3—C21—H21C109.5
O2—C15—C16106.63 (8)H21A—C21—H21C109.5
O2—C15—H15A110.4H21B—C21—H21C109.5
C16—C15—H15A110.4
C6—C1—C2—C30.45 (15)C17B—N2—C13—C1244.5 (5)
C1—C2—C3—C4−0.67 (14)C7—N2—C13—C80.23 (10)
C1—C2—C3—C21178.44 (9)C17—N2—C13—C8−161.60 (10)
C2—C3—C4—C50.58 (15)C17B—N2—C13—C8−135.9 (5)
C21—C3—C4—C5−178.53 (9)C11—C12—C13—N2179.26 (10)
C3—C4—C5—C6−0.26 (15)C11—C12—C13—C8−0.27 (14)
C4—C5—C6—C10.02 (14)N1—C8—C13—N2−0.09 (10)
C4—C5—C6—C7175.50 (9)C9—C8—C13—N2−179.20 (8)
C2—C1—C6—C5−0.12 (14)N1—C8—C13—C12179.55 (9)
C2—C1—C6—C7−175.48 (9)C9—C8—C13—C120.43 (14)
C8—N1—C7—N20.25 (10)C15—O2—C14—O1−1.73 (15)
C8—N1—C7—C6−175.82 (8)C15—O2—C14—C10178.60 (8)
C13—N2—C7—N1−0.31 (11)C9—C10—C14—O1174.76 (10)
C17—N2—C7—N1161.42 (10)C11—C10—C14—O1−3.91 (15)
C17B—N2—C7—N1138.9 (4)C9—C10—C14—O2−5.57 (13)
C13—N2—C7—C6175.74 (9)C11—C10—C14—O2175.76 (8)
C17—N2—C7—C6−22.52 (15)C14—O2—C15—C16170.62 (10)
C17B—N2—C7—C6−45.1 (5)C13—N2—C17—C1951.97 (14)
C5—C6—C7—N1−38.44 (13)C7—N2—C17—C19−106.28 (11)
C1—C6—C7—N1136.90 (10)C17B—N2—C17—C19−36.7 (9)
C5—C6—C7—N2145.86 (9)C13—N2—C17—C18−75.12 (14)
C1—C6—C7—N2−38.79 (13)C7—N2—C17—C18126.63 (11)
C7—N1—C8—C9178.93 (9)C17B—N2—C17—C18−163.7 (10)
C7—N1—C8—C13−0.10 (10)N2—C17—C19—C2051.24 (13)
N1—C8—C9—C10−179.49 (9)C18—C17—C19—C20177.66 (10)
C13—C8—C9—C10−0.55 (13)C13—N2—C17B—C18B43.5 (10)
C8—C9—C10—C110.54 (14)C7—N2—C17B—C18B−88.4 (9)
C8—C9—C10—C14−178.09 (8)C17—N2—C17B—C18B149.4 (15)
C9—C10—C11—C12−0.41 (15)C13—N2—C17B—C19B−82.6 (7)
C14—C10—C11—C12178.26 (9)C7—N2—C17B—C19B145.4 (5)
C10—C11—C12—C130.26 (14)C17—N2—C17B—C19B23.2 (7)
C7—N2—C13—C12−179.36 (10)C18B—C17B—C19B—C20B178.5 (9)
C17—N2—C13—C1218.81 (17)N2—C17B—C19B—C20B−51.9 (10)

Hydrogen-bond geometry (Å, °)

Cg1 is centroid of the N1/C7/N2/C13/C8 ring.
D—H···AD—HH···AD···AD—H···A
C12—H12A···O1i0.932.583.5007 (13)173
C20—H20C···Cg10.962.723.3432 (13)123

Symmetry codes: (i) −x+1, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5024).

References

  • Arumugam, N., Abd Hamid, S., Abdul Rahim, A. S., Hemamalini, M. & Fun, H.-K. (2010a). Acta Cryst. E66, o776–o777. [PMC free article] [PubMed]
  • Arumugam, N., Abdul Rahim, A. S., Abd Hamid, S., Hemamalini, M. & Fun, H.-K. (2010b). Acta Cryst. E66, o796–o797. [PMC free article] [PubMed]
  • Arumugam, N., Abdul Rahim, A. S., Osman, H., Hemamalini, M. & Fun, H.-K. (2010c). Acta Cryst. E66, o845. [PMC free article] [PubMed]
  • Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Can-Eke, B., Puskullu, M. O., Buyukbingol, E. & Iscan, M. (1998). Chem. Biol. Interact.113, 65–67. [PubMed]
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107.
  • Evans, T. M., Gardiner, J. M., Mahmood, N. & Smis, M. (1997). Bioorg. Med. Chem. Lett.7, 409–412.
  • Garuti, L., Roberti, M., Malagoli, M., Rossi, T. & Castelli, M. (2000). Bioorg. Med. Chem. Lett.10, 2193–2195. [PubMed]
  • Richter, J. E. (1997). Am. J. Gastroenterol.92, 34–34.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sondhi, S. M., Singh, N., Lahoti, A. M., Bajaj, K., Kumar, A., Lozech, O. & Meijer, L. (2005). Bioorg. Med. Chem.13, 4291–4299. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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