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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1014.
Published online 2009 April 10. doi:  10.1107/S1600536809012781
PMCID: PMC2977701

1,3-Bis(1-benzyl-1H-benzimidazol-2-yl)-2-oxapropane

Abstract

In the title compound, C30H26N4O, the dihedral angle between the two benzimidazole rings is 69.35 (9)°. The dihedral angles between the benzimidazole ring system and the phenyl ring are 76.79 (12) and 86.10 (11)° in the two benzyl­benzimidazole moieties.

Related literature

For the biological activity of the benzimidazole core, see: Horton et al. (2003 [triangle]). For the anti­protozoal activity of 2- and 5-substituted benzimidazoles, see: Navarrete-Vázquez et al. (2001 [triangle]).

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Object name is e-65-o1014-scheme1.jpg

Experimental

Crystal data

  • C30H26N4O
  • M r = 458.55
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1014-efi1.jpg
  • a = 8.5477 (3) Å
  • b = 11.8976 (5) Å
  • c = 12.3961 (5) Å
  • α = 101.300 (1)°
  • β = 92.394 (1)°
  • γ = 107.765 (1)°
  • V = 1170.28 (8) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 153 K
  • 0.58 × 0.52 × 0.19 mm

Data collection

  • Rigaku R-AXIS Spider diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.955, T max = 0.985
  • 11531 measured reflections
  • 5275 independent reflections
  • 4542 reflections with I > 2σ(I)
  • R int = 0.013

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.126
  • S = 1.09
  • 5275 reflections
  • 317 parameters
  • H-atom parameters constrained
  • Δρmax = 0.50 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012781/lh2800sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012781/lh2800Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support and a grant from the ‘Qing Lan’ Talent Engineering Funds and Students’ Science and Technology Innovation Funds (grant No. DXS2008–040,041) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25–023) and ‘Long Yuan Qing Nian’ of Gansu Province is also acknowledged.

supplementary crystallographic information

Comment

Benzimidazole derivatives, such as mebendazole and albendazole, are used as anthelmintic drugs. More recently, the antiprotozoal activity of 2- and 5-substituted benzimidazoles has been reported (Navarrete-Vázquez et al. 2001). The benzimidazole core is of interest because of its diverse biological activities, and it is a well known structure in medicinal chemistry (Horton et al. 2003). The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between N3/N4/C10-C16 and C18-C23 is 76.79 (12)° and that between N1/N2/C1-C7 and C25-C30 is 86.10 (11)°.

Experimental

A solution of 5.56 (20 mmol) of 1,3-bis(benzimidazol-2-yl)-2-oxopropane with 1.56 g (40 mmol) potassium in 150 ml tetrahydrofuran followed by addition of 5.06 g (40 mmol) benzyl bromide was concentrated and recrystallized from methanol, formimg white block crystals suitable for X-ray diffraction studies. (found: C, 78.51; H, 5.73; N,12.24 Calcd. for C30H26N4O: C, 78.58; H, 5.71; N, 12.22)

Refinement

All H atoms were positioned geometrically with C—H distances ranging from 0.95 to 0.99 Å and allowed to ride on their parent atoms with Uiso(H) = 1.2 Ueq of the carrier atom.

Figures

Fig. 1.
Molecular structure of the title compound. Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level.

Crystal data

C30H26N4OZ = 2
Mr = 458.55F(000) = 484
Triclinic, P1Dx = 1.301 Mg m3
Hall symbol: -P 1Melting point = 450–451 K
a = 8.5477 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.8976 (5) ÅCell parameters from 5275 reflections
c = 12.3961 (5) Åθ = 3.0–27.5°
α = 101.300 (1)°µ = 0.08 mm1
β = 92.394 (1)°T = 153 K
γ = 107.765 (1)°Block, white
V = 1170.28 (8) Å30.58 × 0.52 × 0.19 mm

Data collection

Rigaku R-AXIS Spider diffractometer5275 independent reflections
Radiation source: fine-focus sealed tube4542 reflections with I > 2σ(I)
graphiteRint = 0.013
[var phi] and ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −11→10
Tmin = 0.955, Tmax = 0.985k = −15→15
11531 measured reflectionsl = −16→16

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.126w = 1/[σ2(Fo2) + (0.0736P)2 + 0.3041P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
5275 reflectionsΔρmax = 0.50 e Å3
317 parametersΔρmin = −0.34 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.044 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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*/Ueq
O0.80479 (11)0.49510 (8)0.70677 (7)0.0252 (2)
N10.73219 (13)0.71312 (9)0.90708 (8)0.0233 (2)
N20.54296 (12)0.52783 (9)0.85764 (8)0.0214 (2)
N30.99857 (12)0.31236 (9)0.79071 (8)0.0231 (2)
N40.77779 (12)0.22141 (9)0.66368 (8)0.0231 (2)
C10.58038 (15)0.71864 (10)0.93941 (9)0.0213 (2)
C20.53783 (16)0.81685 (11)0.99680 (10)0.0256 (3)
H20.61720.89531.01820.031*
C30.37662 (17)0.79594 (12)1.02133 (10)0.0276 (3)
H30.34510.86101.06110.033*
C40.25816 (16)0.68035 (12)0.98864 (10)0.0276 (3)
H40.14830.66951.00650.033*
C50.29667 (15)0.58181 (11)0.93114 (10)0.0247 (3)
H50.21640.50390.90860.030*
C60.46015 (15)0.60377 (10)0.90831 (9)0.0208 (2)
C70.70389 (15)0.59876 (11)0.85997 (9)0.0217 (2)
C80.83822 (16)0.55036 (12)0.82143 (10)0.0264 (3)
H8A0.94460.61710.83490.032*
H8B0.84810.49020.86400.032*
C90.92732 (15)0.44005 (11)0.67180 (10)0.0258 (3)
H9A1.03850.49750.70130.031*
H9B0.92080.42270.59000.031*
C100.90483 (14)0.32529 (11)0.71040 (10)0.0222 (2)
C110.79369 (14)0.13374 (11)0.71787 (9)0.0221 (2)
C120.70094 (16)0.01242 (12)0.70590 (11)0.0284 (3)
H120.6078−0.02570.65200.034*
C130.75138 (17)−0.04945 (12)0.77646 (11)0.0295 (3)
H130.6919−0.13250.77060.035*
C140.88820 (17)0.00726 (12)0.85663 (11)0.0283 (3)
H140.9187−0.03820.90400.034*
C150.98002 (15)0.12805 (12)0.86844 (10)0.0258 (3)
H151.07220.16610.92310.031*
C160.93194 (14)0.19187 (10)0.79690 (10)0.0212 (2)
C170.64947 (15)0.20654 (12)0.57568 (10)0.0257 (3)
H17A0.61590.28030.58730.031*
H17B0.55160.13780.58080.031*
C180.70267 (15)0.18411 (11)0.46087 (10)0.0236 (3)
C190.66731 (18)0.24654 (12)0.38477 (11)0.0312 (3)
H190.61150.30400.40570.037*
C200.7125 (2)0.22588 (14)0.27833 (12)0.0403 (4)
H200.68690.26860.22660.048*
C210.7950 (2)0.14290 (14)0.24755 (12)0.0393 (3)
H210.82750.12940.17500.047*
C220.82983 (19)0.07973 (13)0.32288 (12)0.0363 (3)
H220.88610.02250.30200.044*
C230.78271 (17)0.09980 (12)0.42866 (11)0.0303 (3)
H230.80550.05530.47970.036*
C240.46863 (16)0.39871 (10)0.81196 (10)0.0250 (3)
H24A0.39010.36350.86220.030*
H24B0.55650.36030.80950.030*
C250.37816 (14)0.36798 (10)0.69711 (10)0.0214 (2)
C260.28424 (15)0.24803 (12)0.65272 (12)0.0289 (3)
H260.27730.18850.69500.035*
C270.20114 (18)0.21494 (13)0.54754 (13)0.0383 (3)
H270.13830.13270.51790.046*
C280.20876 (18)0.30063 (14)0.48511 (12)0.0382 (3)
H280.15050.27780.41320.046*
C290.30168 (19)0.41940 (14)0.52837 (12)0.0352 (3)
H290.30790.47870.48590.042*
C300.38665 (17)0.45315 (12)0.63410 (11)0.0287 (3)
H300.45080.53520.66310.034*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O0.0294 (4)0.0282 (4)0.0204 (4)0.0137 (4)0.0023 (3)0.0041 (3)
N10.0256 (5)0.0211 (5)0.0220 (5)0.0072 (4)−0.0003 (4)0.0032 (4)
N20.0266 (5)0.0177 (5)0.0187 (5)0.0064 (4)−0.0011 (4)0.0031 (4)
N30.0228 (5)0.0223 (5)0.0224 (5)0.0066 (4)0.0023 (4)0.0019 (4)
N40.0236 (5)0.0234 (5)0.0208 (5)0.0060 (4)−0.0005 (4)0.0043 (4)
C10.0254 (6)0.0206 (5)0.0176 (5)0.0066 (4)0.0005 (4)0.0051 (4)
C20.0331 (6)0.0207 (6)0.0217 (6)0.0085 (5)0.0023 (5)0.0023 (4)
C30.0374 (7)0.0288 (6)0.0200 (6)0.0159 (5)0.0062 (5)0.0044 (5)
C40.0297 (6)0.0346 (7)0.0204 (6)0.0120 (5)0.0047 (5)0.0075 (5)
C50.0265 (6)0.0262 (6)0.0192 (5)0.0046 (5)0.0011 (4)0.0060 (4)
C60.0268 (6)0.0208 (5)0.0147 (5)0.0072 (4)0.0002 (4)0.0045 (4)
C70.0250 (6)0.0221 (6)0.0181 (5)0.0079 (4)−0.0011 (4)0.0046 (4)
C80.0286 (6)0.0284 (6)0.0225 (6)0.0128 (5)−0.0019 (5)0.0015 (5)
C90.0272 (6)0.0257 (6)0.0260 (6)0.0094 (5)0.0086 (5)0.0065 (5)
C100.0217 (5)0.0223 (6)0.0217 (5)0.0071 (4)0.0051 (4)0.0021 (4)
C110.0240 (6)0.0232 (6)0.0182 (5)0.0071 (5)0.0030 (4)0.0034 (4)
C120.0294 (6)0.0251 (6)0.0243 (6)0.0019 (5)−0.0017 (5)0.0022 (5)
C130.0358 (7)0.0217 (6)0.0281 (6)0.0046 (5)0.0050 (5)0.0056 (5)
C140.0343 (7)0.0292 (6)0.0253 (6)0.0138 (5)0.0050 (5)0.0083 (5)
C150.0256 (6)0.0290 (6)0.0224 (6)0.0099 (5)0.0003 (5)0.0036 (5)
C160.0209 (5)0.0211 (5)0.0201 (5)0.0064 (4)0.0040 (4)0.0011 (4)
C170.0225 (6)0.0314 (6)0.0229 (6)0.0092 (5)0.0002 (5)0.0048 (5)
C180.0225 (6)0.0210 (5)0.0230 (6)0.0025 (4)−0.0037 (4)0.0030 (4)
C190.0393 (7)0.0268 (6)0.0285 (6)0.0122 (5)−0.0017 (5)0.0070 (5)
C200.0543 (9)0.0395 (8)0.0271 (7)0.0124 (7)−0.0023 (6)0.0127 (6)
C210.0470 (8)0.0395 (8)0.0243 (6)0.0057 (6)0.0046 (6)0.0036 (6)
C220.0408 (8)0.0321 (7)0.0352 (7)0.0125 (6)0.0092 (6)0.0032 (6)
C230.0348 (7)0.0297 (6)0.0298 (7)0.0132 (5)0.0044 (5)0.0096 (5)
C240.0343 (6)0.0171 (5)0.0223 (6)0.0064 (5)0.0001 (5)0.0048 (4)
C250.0205 (5)0.0211 (6)0.0217 (6)0.0071 (4)0.0030 (4)0.0019 (4)
C260.0247 (6)0.0222 (6)0.0367 (7)0.0056 (5)0.0011 (5)0.0027 (5)
C270.0330 (7)0.0272 (7)0.0438 (8)0.0053 (5)−0.0093 (6)−0.0076 (6)
C280.0369 (7)0.0422 (8)0.0285 (7)0.0121 (6)−0.0081 (6)−0.0050 (6)
C290.0403 (7)0.0370 (7)0.0262 (7)0.0099 (6)−0.0040 (6)0.0077 (6)
C300.0337 (7)0.0238 (6)0.0245 (6)0.0044 (5)−0.0022 (5)0.0046 (5)

Geometric parameters (Å, °)

O—C81.4211 (14)C13—H130.9500
O—C91.4350 (14)C14—C151.3865 (18)
N1—C71.3141 (15)C14—H140.9500
N1—C11.3907 (16)C15—C161.3985 (17)
N2—C71.3726 (15)C15—H150.9500
N2—C61.3846 (15)C17—C181.5108 (17)
N2—C241.4553 (14)C17—H17A0.9900
N3—C101.3136 (16)C17—H17B0.9900
N3—C161.3905 (15)C18—C231.3850 (18)
N4—C101.3748 (15)C18—C191.3859 (18)
N4—C111.3825 (15)C19—C201.387 (2)
N4—C171.4596 (15)C19—H190.9500
C1—C21.3996 (17)C20—C211.384 (2)
C1—C61.4056 (16)C20—H200.9500
C2—C31.3816 (18)C21—C221.383 (2)
C2—H20.9500C21—H210.9500
C3—C41.4065 (19)C22—C231.385 (2)
C3—H30.9500C22—H220.9500
C4—C51.3851 (18)C23—H230.9500
C4—H40.9500C24—C251.5134 (16)
C5—C61.3929 (17)C24—H24A0.9900
C5—H50.9500C24—H24B0.9900
C7—C81.4898 (17)C25—C301.3828 (17)
C8—H8A0.9900C25—C261.3930 (16)
C8—H8B0.9900C26—C271.382 (2)
C9—C101.4945 (17)C26—H260.9500
C9—H9A0.9900C27—C281.384 (2)
C9—H9B0.9900C27—H270.9500
C11—C121.3935 (17)C28—C291.378 (2)
C11—C161.4049 (16)C28—H280.9500
C12—C131.3811 (19)C29—C301.3938 (18)
C12—H120.9500C29—H290.9500
C13—C141.4033 (19)C30—H300.9500
C8—O—C9110.65 (9)C13—C14—H14119.2
C7—N1—C1104.47 (10)C14—C15—C16117.55 (11)
C7—N2—C6106.33 (9)C14—C15—H15121.2
C7—N2—C24128.47 (10)C16—C15—H15121.2
C6—N2—C24125.20 (10)N3—C16—C15130.02 (11)
C10—N3—C16104.83 (10)N3—C16—C11109.99 (10)
C10—N4—C11106.39 (10)C15—C16—C11119.97 (11)
C10—N4—C17127.05 (11)N4—C17—C18113.67 (10)
C11—N4—C17126.55 (10)N4—C17—H17A108.8
N1—C1—C2129.86 (11)C18—C17—H17A108.8
N1—C1—C6110.28 (10)N4—C17—H17B108.8
C2—C1—C6119.85 (11)C18—C17—H17B108.8
C3—C2—C1117.78 (11)H17A—C17—H17B107.7
C3—C2—H2121.1C23—C18—C19118.91 (12)
C1—C2—H2121.1C23—C18—C17121.38 (11)
C2—C3—C4121.34 (12)C19—C18—C17119.69 (11)
C2—C3—H3119.3C18—C19—C20120.65 (13)
C4—C3—H3119.3C18—C19—H19119.7
C5—C4—C3122.06 (12)C20—C19—H19119.7
C5—C4—H4119.0C21—C20—C19119.97 (13)
C3—C4—H4119.0C21—C20—H20120.0
C4—C5—C6116.01 (11)C19—C20—H20120.0
C4—C5—H5122.0C22—C21—C20119.69 (13)
C6—C5—H5122.0C22—C21—H21120.2
N2—C6—C5131.85 (11)C20—C21—H21120.2
N2—C6—C1105.17 (10)C21—C22—C23120.05 (14)
C5—C6—C1122.96 (11)C21—C22—H22120.0
N1—C7—N2113.75 (11)C23—C22—H22120.0
N1—C7—C8122.39 (11)C18—C23—C22120.71 (12)
N2—C7—C8123.68 (11)C18—C23—H23119.6
O—C8—C7110.75 (10)C22—C23—H23119.6
O—C8—H8A109.5N2—C24—C25114.13 (10)
C7—C8—H8A109.5N2—C24—H24A108.7
O—C8—H8B109.5C25—C24—H24A108.7
C7—C8—H8B109.5N2—C24—H24B108.7
H8A—C8—H8B108.1C25—C24—H24B108.7
O—C9—C10112.03 (10)H24A—C24—H24B107.6
O—C9—H9A109.2C30—C25—C26118.82 (11)
C10—C9—H9A109.2C30—C25—C24122.96 (11)
O—C9—H9B109.2C26—C25—C24118.21 (11)
C10—C9—H9B109.2C27—C26—C25120.48 (13)
H9A—C9—H9B107.9C27—C26—H26119.8
N3—C10—N4113.39 (11)C25—C26—H26119.8
N3—C10—C9125.14 (11)C26—C27—C28120.52 (13)
N4—C10—C9121.46 (11)C26—C27—H27119.7
N4—C11—C12131.98 (11)C28—C27—H27119.7
N4—C11—C16105.38 (10)C29—C28—C27119.31 (13)
C12—C11—C16122.64 (11)C29—C28—H28120.3
C13—C12—C11116.55 (11)C27—C28—H28120.3
C13—C12—H12121.7C28—C29—C30120.41 (13)
C11—C12—H12121.7C28—C29—H29119.8
C12—C13—C14121.68 (12)C30—C29—H29119.8
C12—C13—H13119.2C25—C30—C29120.44 (12)
C14—C13—H13119.2C25—C30—H30119.8
C15—C14—C13121.61 (12)C29—C30—H30119.8
C15—C14—H14119.2
C7—N1—C1—C2177.64 (12)C17—N4—C11—C16−178.40 (11)
C7—N1—C1—C6−0.91 (12)N4—C11—C12—C13−179.01 (13)
N1—C1—C2—C3−178.07 (12)C16—C11—C12—C130.11 (19)
C6—C1—C2—C30.35 (17)C11—C12—C13—C140.5 (2)
C1—C2—C3—C4−0.82 (18)C12—C13—C14—C15−0.4 (2)
C2—C3—C4—C50.42 (19)C13—C14—C15—C16−0.32 (19)
C3—C4—C5—C60.47 (18)C10—N3—C16—C15−178.95 (12)
C7—N2—C6—C5−178.66 (12)C10—N3—C16—C11−0.61 (13)
C24—N2—C6—C51.42 (19)C14—C15—C16—N3179.09 (12)
C7—N2—C6—C1−0.40 (12)C14—C15—C16—C110.90 (17)
C24—N2—C6—C1179.68 (10)N4—C11—C16—N3−0.03 (13)
C4—C5—C6—N2177.04 (12)C12—C11—C16—N3−179.35 (11)
C4—C5—C6—C1−0.95 (17)N4—C11—C16—C15178.50 (10)
N1—C1—C6—N20.82 (12)C12—C11—C16—C15−0.82 (18)
C2—C1—C6—N2−177.89 (10)C10—N4—C17—C1882.90 (15)
N1—C1—C6—C5179.27 (10)C11—N4—C17—C18−98.27 (14)
C2—C1—C6—C50.56 (17)N4—C17—C18—C2347.20 (16)
C1—N1—C7—N20.66 (13)N4—C17—C18—C19−134.51 (12)
C1—N1—C7—C8−174.66 (11)C23—C18—C19—C20−0.6 (2)
C6—N2—C7—N1−0.17 (13)C17—C18—C19—C20−178.91 (12)
C24—N2—C7—N1179.75 (11)C18—C19—C20—C21−0.5 (2)
C6—N2—C7—C8175.08 (10)C19—C20—C21—C220.9 (2)
C24—N2—C7—C8−5.00 (18)C20—C21—C22—C23−0.2 (2)
C9—O—C8—C7−175.36 (10)C19—C18—C23—C221.3 (2)
N1—C7—C8—O−122.70 (12)C17—C18—C23—C22179.60 (12)
N2—C7—C8—O62.45 (15)C21—C22—C23—C18−0.9 (2)
C8—O—C9—C1074.56 (13)C7—N2—C24—C25−98.23 (14)
C16—N3—C10—N41.06 (13)C6—N2—C24—C2581.68 (14)
C16—N3—C10—C9−179.86 (11)N2—C24—C25—C309.57 (17)
C11—N4—C10—N3−1.10 (14)N2—C24—C25—C26−171.39 (11)
C17—N4—C10—N3177.92 (11)C30—C25—C26—C270.00 (19)
C11—N4—C10—C9179.78 (10)C24—C25—C26—C27−179.08 (12)
C17—N4—C10—C9−1.20 (18)C25—C26—C27—C28−0.6 (2)
O—C9—C10—N3−106.11 (13)C26—C27—C28—C290.7 (2)
O—C9—C10—N472.90 (14)C27—C28—C29—C30−0.3 (2)
C10—N4—C11—C12179.86 (13)C26—C25—C30—C290.43 (19)
C17—N4—C11—C120.8 (2)C24—C25—C30—C29179.46 (13)
C10—N4—C11—C160.63 (13)C28—C29—C30—C25−0.3 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2800).

References

  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev.103, 893–930. [PubMed]
  • Navarrete-Vázquez, G., Cedillo, R., Hernández-Campos, A., Yépez, L., Hernández-Luis, F., Valdez, J., Morales, R., Cortés, R., Hernández, M. & Castillo, R. (2001). Bioorg. Med. Chem. Lett.11, 187–190. [PubMed]
  • Rigaku/MSC (2004). RAPID-AUTO . Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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