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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2136.
Published online 2009 August 12. doi:  10.1107/S1600536809031213
PMCID: PMC2970106

1-Cyclo­hexyl-2-(3-fur­yl)-1H-benzimidazole-5-carboxylic acid

Abstract

The asymmetric unit of the title compound, C18H18N2O3, contains two mol­ecules. The fused rings of both mol­ecules are almost planar, with dihedral angles of 3.1 (1) and 2.8 (2)° between the fused rings. The furan rings are rotated by 43.85 (15) and −21.07 (9)° with respect to the planes of the attached bnzimidazole systems. In the crystal, mol­ecules are linked into infinite chains by inter­molecular O—H(...)N hydrogen bonds.

Related literature

For general background, see Beaulieu et al. (2004a [triangle]). For the synthesis, see Beaulieu et al. (2004b [triangle]).

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Object name is e-65-o2136-scheme1.jpg

Experimental

Crystal data

  • C18H18N2O3
  • M r = 310.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2136-efi3.jpg
  • a = 9.1402 (3) Å
  • b = 11.2446 (3) Å
  • c = 15.6061 (5) Å
  • β = 101.334 (2)°
  • V = 1572.68 (8) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 0.74 mm−1
  • T = 100 K
  • 0.50 × 0.50 × 0.45 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.710, T max = 0.733
  • 7859 measured reflections
  • 4379 independent reflections
  • 4006 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.143
  • S = 1.06
  • 4379 reflections
  • 423 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.73 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; 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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031213/rk2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031213/rk2157Isup2.hkl

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

Acknowledgments

All authors contributed equally to this paper. We thank Bao Ho and Cody Higginson for help with compound synthesis and James Golen for help with the structural solution. This work was supported in part by the National Institutes of Health, grant R01 AI72012.

supplementary crystallographic information

Comment

The title compound is an allosteric inhibitor of the RNA–dependent RNA polymerase NS5B of hepatitis C virus (HCV) (Beaulieu et al., 2004a). The inhibitor binds with low micromolar affinity (4.3 mM) to the NS5B polymerase and prevents replication of subgenomic HCV replicon in human cells (Beaulieu et al., 2004b). The title compound was synthesized following the route described by Beaulieu et al., (2004b). We report here the single–crystal X–ray structure.

Asymmetric unit of the title compound is composed of molecule 1 and molecule 2 (Fig. 1). They are linked together into infinite non–interacting chains by the intermolecular O2—H2···N2i and O4—H4···N4ii hydrogen bonds along the b axis (Fig. 2). Symmetry codes: (i) -x + 1, y + 1/2, -z + 1 and (ii) -x, y + 1/2, -z.

Experimental

1-Cyclohexyl-2-(furan-3-yl)-1H-benzo[d]imidazole-5-carboxylic acid was prepared according to the literature procedure (Beaulieu et al., 2004b). In a sample vial, 15 mg of compound was taken and dissolved in CH2Cl2DMSO/ 9:1 mixture. Upon slow evaporation at 273 K within 2 months the crystals are formed as colourless blocks.

Refinement

Acidic H2 and H4 hydrgen atoms were located in a Fourier difference map and refined freely with distances obtained for O2—H2 = 1.00 (5) and O4—H4 = 0.76 (5). Other H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2 Ueq(C).

The highest density value is peak with a value of 0.73 e Å-3 at coordinates 0.5281 0.1307 0.9370 that is 1.21Å from atom H6 and 1.24Å from atom C17.

1455 Friedel pairs were merged.

Figures

Fig. 1.
The asymmetric units of structure of title compound, with the atom–numbering scheme. The displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
Fig. 2.
The crystal packing of one of the two molecules, viewed down the a axis, showing the molecules are linked along the b axis. Intermolecular hydrogen bonds are shown as dashed lines. Symmetry codes: (i) -x + 1, y + 1/2, -z + 1 and (ii) -x + 1, y - 1/2, ...

Crystal data

C18H18N2O3F(000) = 656
Mr = 310.34Dx = 1.311 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ybCell parameters from 5005 reflections
a = 9.1402 (3) Åθ = 2.9–65.6°
b = 11.2446 (3) ŵ = 0.74 mm1
c = 15.6061 (5) ÅT = 100 K
β = 101.334 (2)°Block, colourless
V = 1572.68 (8) Å30.50 × 0.50 × 0.45 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer4379 independent reflections
Radiation source: fine-focus sealed tube4006 reflections with I > 2σ(I)
graphiteRint = 0.027
[var phi] and ω scansθmax = 66.4°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −10→10
Tmin = 0.710, Tmax = 0.733k = −13→12
7859 measured reflectionsl = −18→17

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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0919P)2 + 0.4805P] where P = (Fo2 + 2Fc2)/3
4379 reflections(Δ/σ)max = 0.007
423 parametersΔρmax = 0.73 e Å3
1 restraintΔρmin = −0.29 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O10.5638 (3)0.67629 (19)0.56838 (16)0.0384 (6)
O20.5668 (3)0.5223 (2)0.47898 (14)0.0335 (5)
H20.574 (5)0.581 (4)0.432 (3)0.059 (13)*
O30.3079 (3)−0.1746 (2)0.74288 (17)0.0496 (7)
N10.4370 (3)0.2274 (3)0.79176 (17)0.0330 (6)
N20.4291 (3)0.1685 (2)0.65399 (17)0.0283 (6)
C10.5558 (3)0.5707 (3)0.5547 (2)0.0292 (7)
C20.5294 (4)0.4824 (3)0.6213 (2)0.0277 (7)
C30.5382 (4)0.5195 (3)0.7078 (2)0.0345 (8)
H30.56280.60000.72240.041*
C40.5126 (4)0.4436 (3)0.7724 (2)0.0358 (8)
H4B0.51860.46960.83090.043*
C50.4767 (4)0.3249 (3)0.7470 (2)0.0297 (7)
C60.4321 (5)0.2198 (4)0.8860 (2)0.0465 (9)
H60.40300.13560.89460.056*
C70.3093 (4)0.2922 (4)0.9103 (2)0.0448 (9)
H7A0.21320.26870.87280.054*
H7B0.32650.37730.89910.054*
C80.2991 (6)0.2766 (6)1.0046 (3)0.0717 (15)
H8A0.23190.33851.02030.086*
H8B0.25340.19831.01160.086*
C90.4430 (6)0.2838 (8)1.0658 (3)0.093 (2)
H9A0.42900.26131.12500.111*
H9B0.47930.36691.06840.111*
C100.4080 (4)0.1373 (3)0.7332 (2)0.0310 (7)
C110.4698 (3)0.2865 (3)0.6616 (2)0.0267 (7)
C120.4959 (3)0.3654 (3)0.5968 (2)0.0267 (7)
H120.49090.33980.53830.032*
C130.3512 (4)0.0199 (3)0.7503 (2)0.0359 (8)
C140.3900 (5)−0.0844 (3)0.7186 (3)0.0432 (9)
H140.4641−0.09350.68420.052*
C150.2130 (5)−0.1246 (4)0.7902 (3)0.0476 (10)
H150.1418−0.16750.81490.057*
C160.2339 (4)−0.0080 (3)0.7971 (2)0.0396 (9)
H160.18200.04640.82690.047*
C170.5769 (5)0.2333 (5)0.9441 (3)0.0608 (12)
H17A0.61210.31640.94210.073*
H17B0.65090.18030.92510.073*
C180.5620 (5)0.2013 (6)1.0386 (3)0.0738 (17)
H18A0.65910.21211.07900.089*
H18B0.53150.11721.04130.089*
O4−0.0250 (4)1.0807 (2)−0.01851 (16)0.0440 (7)
H4−0.071 (5)1.119 (4)−0.053 (3)0.047 (13)*
O5−0.0456 (3)1.2233 (2)0.07781 (15)0.0367 (6)
O60.1913 (3)0.3434 (2)0.23203 (17)0.0481 (7)
N30.1075 (3)0.7453 (2)0.30021 (16)0.0274 (6)
N40.1229 (3)0.7088 (2)0.16093 (17)0.0294 (6)
C19−0.0173 (4)1.1217 (3)0.0617 (2)0.0313 (7)
C200.0290 (4)1.0279 (3)0.1289 (2)0.0306 (7)
C210.0299 (4)1.0543 (3)0.2180 (2)0.0339 (8)
H210.01151.13370.23400.041*
C220.0563 (4)0.9688 (3)0.2813 (2)0.0336 (8)
H220.05630.98790.34060.040*
C230.0834 (4)0.8530 (3)0.2568 (2)0.0277 (7)
C240.0788 (4)0.7156 (3)0.3880 (2)0.0344 (8)
H240.06360.62750.38740.041*
C25−0.0670 (4)0.7689 (4)0.4042 (2)0.0447 (9)
H25A−0.05870.85660.40730.054*
H25B−0.14960.74810.35530.054*
C26−0.1004 (4)0.7210 (4)0.4894 (2)0.0508 (10)
H26A−0.19110.76030.50160.061*
H26B−0.12070.63460.48340.061*
C270.0277 (4)0.7422 (4)0.5646 (2)0.0462 (9)
H27A0.00470.70540.61810.055*
H27B0.04010.82880.57500.055*
C280.1737 (4)0.6900 (4)0.5466 (2)0.0470 (10)
H28A0.25670.71050.59540.056*
H28B0.16570.60220.54320.056*
C290.2072 (4)0.7384 (4)0.4609 (2)0.0414 (9)
H29A0.22630.82500.46650.050*
H29B0.29780.69960.44830.050*
C300.1327 (4)0.6622 (3)0.2394 (2)0.0275 (7)
C310.0913 (4)0.8276 (3)0.1692 (2)0.0284 (7)
C320.0629 (4)0.9149 (3)0.1045 (2)0.0314 (7)
H320.06690.89710.04550.038*
C330.1669 (4)0.5375 (3)0.2578 (2)0.0316 (8)
C340.1464 (5)0.4501 (3)0.1967 (2)0.0427 (9)
H340.10560.46240.13650.051*
C350.2435 (4)0.3639 (3)0.3181 (2)0.0402 (9)
H350.28330.30440.35940.048*
C360.2317 (4)0.4778 (3)0.3373 (2)0.0396 (9)
H360.26070.51320.39330.047*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0570 (15)0.0210 (11)0.0376 (13)−0.0062 (11)0.0105 (11)−0.0037 (10)
O20.0536 (14)0.0232 (11)0.0261 (12)−0.0006 (10)0.0141 (10)0.0000 (10)
O30.0725 (19)0.0356 (14)0.0444 (15)−0.0083 (13)0.0205 (13)0.0069 (12)
N10.0425 (15)0.0356 (15)0.0242 (13)0.0028 (13)0.0148 (11)0.0024 (12)
N20.0379 (14)0.0243 (13)0.0250 (14)−0.0011 (11)0.0117 (11)0.0048 (11)
C10.0297 (16)0.0297 (17)0.0278 (17)−0.0007 (13)0.0047 (13)−0.0006 (13)
C20.0328 (16)0.0237 (15)0.0275 (16)0.0003 (13)0.0079 (13)−0.0013 (13)
C30.0452 (19)0.0275 (16)0.0318 (17)−0.0029 (15)0.0103 (14)−0.0042 (15)
C40.048 (2)0.0358 (19)0.0259 (17)−0.0027 (16)0.0119 (14)−0.0061 (15)
C50.0321 (17)0.0330 (17)0.0270 (16)0.0006 (14)0.0132 (13)0.0022 (14)
C60.059 (2)0.059 (2)0.0251 (18)0.012 (2)0.0184 (16)0.0053 (18)
C70.044 (2)0.065 (3)0.0292 (18)0.0042 (19)0.0172 (15)−0.0026 (18)
C80.080 (3)0.104 (4)0.039 (2)0.023 (3)0.031 (2)0.001 (3)
C90.065 (3)0.181 (7)0.036 (2)0.018 (4)0.020 (2)−0.018 (3)
C100.0334 (17)0.0314 (17)0.0308 (18)0.0010 (14)0.0129 (14)−0.0003 (14)
C110.0290 (15)0.0250 (15)0.0272 (16)0.0008 (13)0.0078 (12)0.0015 (13)
C120.0337 (17)0.0238 (15)0.0239 (15)−0.0008 (13)0.0090 (13)0.0002 (13)
C130.0413 (19)0.0357 (18)0.0326 (18)−0.0024 (16)0.0116 (14)0.0075 (15)
C140.059 (2)0.0337 (19)0.042 (2)−0.0020 (18)0.0239 (17)0.0069 (16)
C150.059 (2)0.049 (2)0.040 (2)−0.0145 (19)0.0240 (18)0.0060 (18)
C160.044 (2)0.039 (2)0.0387 (19)−0.0033 (16)0.0165 (16)0.0024 (16)
C170.053 (2)0.087 (3)0.046 (2)0.002 (2)0.0174 (19)−0.006 (2)
C180.052 (2)0.140 (5)0.029 (2)0.014 (3)0.0087 (18)−0.004 (3)
O40.080 (2)0.0250 (12)0.0266 (14)0.0108 (13)0.0106 (13)0.0031 (11)
O50.0565 (15)0.0239 (12)0.0341 (13)0.0049 (11)0.0194 (10)−0.0001 (10)
O60.0618 (17)0.0331 (13)0.0502 (16)0.0133 (12)0.0132 (13)0.0068 (12)
N30.0308 (13)0.0306 (13)0.0229 (13)0.0004 (11)0.0102 (11)0.0017 (11)
N40.0412 (15)0.0223 (13)0.0264 (14)−0.0007 (11)0.0110 (11)0.0007 (11)
C190.0425 (19)0.0275 (18)0.0264 (17)−0.0039 (15)0.0128 (14)−0.0035 (14)
C200.0419 (18)0.0232 (15)0.0286 (16)−0.0032 (14)0.0119 (13)−0.0026 (13)
C210.049 (2)0.0245 (17)0.0315 (18)−0.0046 (14)0.0153 (15)−0.0053 (14)
C220.046 (2)0.0330 (17)0.0237 (16)−0.0020 (15)0.0111 (14)−0.0031 (15)
C230.0319 (17)0.0284 (16)0.0252 (16)−0.0003 (13)0.0115 (13)0.0021 (13)
C240.0462 (19)0.0370 (18)0.0234 (16)0.0058 (16)0.0149 (14)0.0087 (15)
C250.0390 (19)0.060 (2)0.037 (2)0.0021 (18)0.0117 (15)0.0075 (18)
C260.045 (2)0.068 (3)0.044 (2)−0.002 (2)0.0188 (17)0.003 (2)
C270.055 (2)0.056 (2)0.0303 (18)0.0059 (19)0.0165 (16)0.0051 (18)
C280.050 (2)0.060 (3)0.0288 (19)−0.003 (2)0.0045 (16)0.0063 (18)
C290.0390 (19)0.050 (2)0.0376 (19)0.0004 (17)0.0135 (15)−0.0036 (17)
C300.0303 (16)0.0280 (16)0.0266 (16)−0.0033 (13)0.0115 (13)0.0032 (13)
C310.0356 (17)0.0237 (15)0.0279 (16)−0.0019 (13)0.0111 (13)−0.0016 (13)
C320.0461 (19)0.0281 (16)0.0220 (16)−0.0053 (15)0.0115 (13)−0.0027 (13)
C330.0312 (17)0.0310 (17)0.0356 (18)0.0018 (14)0.0137 (14)0.0069 (15)
C340.063 (2)0.0302 (18)0.038 (2)0.0144 (17)0.0168 (17)0.0068 (16)
C350.0377 (19)0.037 (2)0.046 (2)0.0070 (15)0.0099 (16)0.0137 (17)
C360.041 (2)0.040 (2)0.0349 (19)0.0012 (16)0.0021 (15)0.0108 (17)

Geometric parameters (Å, °)

O1—C11.207 (4)O4—C191.324 (4)
O2—C11.322 (4)O4—H40.75 (5)
O2—H20.99 (5)O5—C191.208 (4)
O3—C141.359 (5)O6—C341.350 (4)
O3—C151.366 (5)O6—C351.354 (5)
N1—C101.355 (4)N3—C231.383 (4)
N1—C51.387 (4)N3—C301.383 (4)
N1—C61.482 (4)N3—C241.482 (4)
N2—C101.335 (4)N4—C301.319 (4)
N2—C111.377 (4)N4—C311.378 (4)
C1—C21.492 (5)C19—C201.489 (5)
C2—C121.387 (4)C20—C321.378 (5)
C2—C31.400 (4)C20—C211.421 (5)
C3—C41.376 (5)C21—C221.366 (5)
C3—H30.9500C21—H210.9500
C4—C51.411 (5)C22—C231.393 (5)
C4—H4B0.9500C22—H220.9500
C5—C111.391 (4)C23—C311.413 (4)
C6—C171.459 (6)C24—C291.488 (5)
C6—C71.495 (6)C24—C251.528 (5)
C6—H61.0000C24—H241.0000
C7—C81.504 (5)C25—C261.518 (5)
C7—H7A0.9900C25—H25A0.9900
C7—H7B0.9900C25—H25B0.9900
C8—C91.468 (7)C26—C271.505 (5)
C8—H8A0.9900C26—H26A0.9900
C8—H8B0.9900C26—H26B0.9900
C9—C181.550 (8)C27—C281.533 (6)
C9—H9A0.9900C27—H27A0.9900
C9—H9B0.9900C27—H27B0.9900
C10—C131.462 (5)C28—C291.530 (5)
C11—C121.401 (4)C28—H28A0.9900
C12—H120.9500C28—H28B0.9900
C13—C141.346 (5)C29—H29A0.9900
C13—C161.447 (5)C29—H29B0.9900
C14—H140.9500C30—C331.452 (5)
C15—C161.326 (6)C31—C321.396 (5)
C15—H150.9500C32—H320.9500
C16—H160.9500C33—C341.358 (5)
C17—C181.549 (6)C33—C361.433 (4)
C17—H17A0.9900C34—H340.9500
C17—H17B0.9900C35—C361.324 (5)
C18—H18A0.9900C35—H350.9500
C18—H18B0.9900C36—H360.9500
C1—O2—H2114 (3)C19—O4—H4114 (3)
C14—O3—C15106.7 (3)C34—O6—C35105.9 (3)
C10—N1—C5106.7 (3)C23—N3—C30106.7 (2)
C10—N1—C6125.9 (3)C23—N3—C24127.5 (3)
C5—N1—C6127.4 (3)C30—N3—C24124.4 (3)
C10—N2—C11105.0 (3)C30—N4—C31106.0 (3)
O1—C1—O2123.4 (3)O5—C19—O4123.5 (3)
O1—C1—C2122.9 (3)O5—C19—C20124.5 (3)
O2—C1—C2113.6 (3)O4—C19—C20111.9 (3)
C12—C2—C3121.1 (3)C32—C20—C21120.4 (3)
C12—C2—C1119.7 (3)C32—C20—C19120.5 (3)
C3—C2—C1119.2 (3)C21—C20—C19119.1 (3)
C4—C3—C2122.3 (3)C22—C21—C20121.8 (3)
C4—C3—H3118.8C22—C21—H21119.1
C2—C3—H3118.8C20—C21—H21119.1
C3—C4—C5116.4 (3)C21—C22—C23118.4 (3)
C3—C4—H4B121.8C21—C22—H22120.8
C5—C4—H4B121.8C23—C22—H22120.8
N1—C5—C11105.6 (3)N3—C23—C22134.8 (3)
N1—C5—C4132.5 (3)N3—C23—C31105.3 (3)
C11—C5—C4121.8 (3)C22—C23—C31119.9 (3)
C17—C6—N1114.3 (3)N3—C24—C29114.3 (3)
C17—C6—C7114.9 (4)N3—C24—C25112.6 (3)
N1—C6—C7113.0 (3)C29—C24—C25112.8 (3)
C17—C6—H6104.4N3—C24—H24105.4
N1—C6—H6104.4C29—C24—H24105.4
C7—C6—H6104.4C25—C24—H24105.4
C6—C7—C8112.3 (3)C26—C25—C24109.8 (3)
C6—C7—H7A109.2C26—C25—H25A109.7
C8—C7—H7A109.2C24—C25—H25A109.7
C6—C7—H7B109.2C26—C25—H25B109.7
C8—C7—H7B109.2C24—C25—H25B109.7
H7A—C7—H7B107.9H25A—C25—H25B108.2
C9—C8—C7114.2 (4)C27—C26—C25111.5 (3)
C9—C8—H8A108.7C27—C26—H26A109.3
C7—C8—H8A108.7C25—C26—H26A109.3
C9—C8—H8B108.7C27—C26—H26B109.3
C7—C8—H8B108.7C25—C26—H26B109.3
H8A—C8—H8B107.6H26A—C26—H26B108.0
C8—C9—C18112.1 (5)C26—C27—C28111.6 (3)
C8—C9—H9A109.2C26—C27—H27A109.3
C18—C9—H9A109.2C28—C27—H27A109.3
C8—C9—H9B109.2C26—C27—H27B109.3
C18—C9—H9B109.2C28—C27—H27B109.3
H9A—C9—H9B107.9H27A—C27—H27B108.0
N2—C10—N1112.6 (3)C29—C28—C27110.8 (3)
N2—C10—C13121.8 (3)C29—C28—H28A109.5
N1—C10—C13125.5 (3)C27—C28—H28A109.5
N2—C11—C5110.1 (3)C29—C28—H28B109.5
N2—C11—C12129.0 (3)C27—C28—H28B109.5
C5—C11—C12120.8 (3)H28A—C28—H28B108.1
C2—C12—C11117.5 (3)C24—C29—C28110.1 (3)
C2—C12—H12121.2C24—C29—H29A109.6
C11—C12—H12121.2C28—C29—H29A109.6
C14—C13—C16105.7 (3)C24—C29—H29B109.6
C14—C13—C10126.2 (3)C28—C29—H29B109.6
C16—C13—C10127.8 (3)H29A—C29—H29B108.1
C13—C14—O3110.4 (3)N4—C30—N3112.2 (3)
C13—C14—H14124.8N4—C30—C33122.7 (3)
O3—C14—H14124.8N3—C30—C33125.1 (3)
C16—C15—O3110.7 (4)N4—C31—C32128.8 (3)
C16—C15—H15124.6N4—C31—C23109.7 (3)
O3—C15—H15124.6C32—C31—C23121.4 (3)
C15—C16—C13106.4 (4)C20—C32—C31117.9 (3)
C15—C16—H16126.8C20—C32—H32121.1
C13—C16—H16126.8C31—C32—H32121.1
C6—C17—C18109.2 (4)C34—C33—C36104.2 (3)
C6—C17—H17A109.8C34—C33—C30124.4 (3)
C18—C17—H17A109.8C36—C33—C30131.3 (3)
C6—C17—H17B109.8O6—C34—C33111.5 (3)
C18—C17—H17B109.8O6—C34—H34124.2
H17A—C17—H17B108.3C33—C34—H34124.2
C17—C18—C9108.6 (4)C36—C35—O6111.1 (3)
C17—C18—H18A110.0C36—C35—H35124.4
C9—C18—H18A110.0O6—C35—H35124.4
C17—C18—H18B110.0C35—C36—C33107.2 (3)
C9—C18—H18B110.0C35—C36—H36126.4
H18A—C18—H18B108.3C33—C36—H36126.4

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···N2i0.99 (5)1.66 (5)2.653 (3)173 (4)
O4—H4···N4ii0.75 (5)1.94 (5)2.653 (4)159 (5)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2157).

References

  • Beaulieu, P. L., Bös, M., Bousquet, Y., Fazal, G., Gauthier, J., Gillard, J., Goulet, S., LaPlante, S., Poupart, M. A., Lefebvre, S., McKercher, G., Pellerin, C., Austel, V. & Kukolj, G. (2004a). Bioorg. Med. Chem. Lett.14, 119–124. [PubMed]
  • Beaulieu, P. L., Bousquet, Y., Gauthier, J., Gillard, J., Marquis, M., McKercher, G., Pellerin, C., Valois, S. & Kukolj, G. (2004b). J. Med. Chem.47, 6884–6892. [PubMed]
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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