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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): o636.
Published online 2010 February 13. doi:  10.1107/S1600536810005209
PMCID: PMC2983564

(1R*,2R*)-1-(7-Bromo-3-methoxy­naphthalen-2-yl)-4-(dimethyl­amino)-2-(naphthalen-1-yl)-1-phenyl­butan-2-ol

Abstract

In the crystal structure of the title compound, C33H32BrNO2, the naphthalene ring system and the benzene ring are oriented at dihedral angles of 82.24 (4) and 79.53 (4)°, respectively, to the quinoline ring system. An intra­molecular O—H(...)N hydrogen bond occurs between the hydr­oxy H atom and the amine N atom.

Related literature

For general background and the synthesis of diaryl­quinoline anti-tuberculosis drugs, see: Cohen (2004 [triangle]), Andries et al. (2005 [triangle]); Guillemont et al. (2004 [triangle])

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Object name is e-66-0o636-scheme1.jpg

Experimental

Crystal data

  • C33H32BrNO2
  • M r = 554.51
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o636-efi1.jpg
  • a = 12.716 (3) Å
  • b = 12.505 (4) Å
  • c = 17.771 (4) Å
  • β = 110.863 (7)°
  • V = 2640.6 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.59 mm−1
  • T = 113 K
  • 0.22 × 0.20 × 0.16 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.721, T max = 0.785
  • 21986 measured reflections
  • 6297 independent reflections
  • 4775 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.066
  • S = 1.01
  • 6297 reflections
  • 338 parameters
  • H-atom parameters constrained
  • Δρmax = 0.44 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: XCIF in SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810005209/nc2176sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005209/nc2176Isup2.hkl

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

Acknowledgments

This work was supported by the 863 Program (2006 A A020601).

supplementary crystallographic information

Comment

The compound (1R*,2R*)-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4- (dimethylamino)-2-(naphthalene-1-\ yl)-1-phenylbutan-2-ol, is a promising drug against tuberculosis (Andries et al., 2005; Cohen, 2004 and Guillemont and Frans, 2004)). We modified this compound in order to get some more efficient antituberculosis drugs. To characterize our product its single crystal structure was determined.

In the molecule of the title compound (Fig. 1), the dihedral angle between the naphthalene ring (C20—C29) and the quinoline ring (C1—C10) amount to 82.244 (39)° whereas the benzene ring (C13—C18) is oriented with respect to the quinoline ring at a dihedral angle of 79.534 (39)°. In the structure an intramolecular O—H···N hydrogen bond is found (Tab. 1).

Experimental

nBuLi (2.5M in hexanes, 4 ml, 10 mmol) was added slowly at 233 K under N2 to a solution of diisopropylamine (1.4 ml, 10 mmol) in THF (15 ml). The mixture was stirred at 233k for 30 min, then cooled to 195 K. Afterwards a solution of 3-benzyl-6-bromo-2-methoxynaphthalene (2.58 g, 9.2 mmol) in THF (20 ml) was added slowly. The mixture was stirred at 195 K for about 40 min and then a solution of 3-(dimethylamino)-1-(naphthalen-1-yl)propan-1-one(2.9 g, 12.8 mmol) in THF (20 ml) was added slowly. The mixture was stirred at 195 K for 8 h, hydrolyzed with ice water at 233 K and extracted with ethyl acetate. The organic layer was separated, dried over MgSO4, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: petroleum ether/ethyl acetate, 50/1).Two fractions were collected (Guillemont et al., 2004). On evaporation of the solvent (petroleum ether/ethyl acetate, 50/1) from fraction at room temperature in air single crystals of the title compound were obtained.

Refinement

All H atoms were positioned with ideal geometry (O-H H atoms allowed to rotate but not to tip) and with d(C—H)= 0.93 Å for aromatic, 0.98 Å for CH, 0.97 Å for CH2 and 0.96 Å for CH3 atoms and were refined with Uiso(H) = 1.2 Ueq(C) for CH and CH2 H atoms and Uiso(H) = 1.5 Ueq(C) for CH3 and O-H H atoms.

Figures

Fig. 1.
The molecular structure of title compound. Displacement ellipsoides a drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.

Crystal data

C33H32BrNO2F(000) = 1152
Mr = 554.51Dx = 1.395 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.716 (3) ÅCell parameters from 9894 reflections
b = 12.505 (4) Åθ = 1.7–27.9°
c = 17.771 (4) ŵ = 1.59 mm1
β = 110.863 (7)°T = 113 K
V = 2640.6 (12) Å3Prism, colorless
Z = 40.22 × 0.20 × 0.16 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer6297 independent reflections
Radiation source: rotating anode4775 reflections with I > 2σ(I)
multilayerRint = 0.039
Detector resolution: 14.63 pixels mm-1θmax = 27.9°, θmin = 2.0°
ω and [var phi] scansh = −14→16
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −16→13
Tmin = 0.721, Tmax = 0.785l = −23→23
21986 measured reflections

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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.026P)2] where P = (Fo2 + 2Fc2)/3
6297 reflections(Δ/σ)max = 0.004
338 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = −0.36 e Å3

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
Br10.855107 (15)−0.301941 (13)0.033962 (11)0.02661 (6)
O11.09459 (9)0.30832 (8)0.16894 (6)0.0200 (3)
O20.70336 (9)0.24821 (9)0.13087 (6)0.0179 (2)
H20.64330.26670.13680.027*
N10.54575 (10)0.37440 (11)0.15453 (7)0.0183 (3)
C10.92349 (13)0.21144 (12)0.11745 (8)0.0149 (3)
C20.86920 (13)0.11576 (12)0.09563 (8)0.0168 (3)
H2A0.78980.11370.08140.020*
C30.92691 (13)0.01955 (12)0.09339 (8)0.0155 (3)
C40.86996 (13)−0.07937 (12)0.06968 (9)0.0180 (3)
H40.7908−0.08350.05660.022*
C50.92952 (14)−0.16813 (13)0.06576 (9)0.0187 (4)
C61.04680 (14)−0.16596 (13)0.08397 (9)0.0197 (4)
H61.0862−0.22910.08020.024*
C71.10257 (13)−0.07195 (13)0.10705 (9)0.0189 (4)
H71.1816−0.06990.11940.023*
C81.04561 (13)0.02292 (13)0.11305 (8)0.0154 (3)
C91.10209 (13)0.12096 (13)0.13816 (8)0.0167 (3)
H91.18150.12410.15240.020*
C101.04431 (13)0.21130 (12)0.14228 (9)0.0161 (3)
C111.21478 (13)0.31054 (13)0.19889 (10)0.0248 (4)
H11A1.24380.25670.24130.037*
H11B1.24100.38150.22100.037*
H11C1.24200.29490.15490.037*
C120.86391 (13)0.31938 (12)0.10741 (9)0.0153 (3)
H120.92500.37320.13110.018*
C130.81297 (13)0.34627 (13)0.01755 (9)0.0156 (3)
C140.86628 (13)0.42324 (12)−0.01233 (9)0.0185 (3)
H140.93110.45820.02360.022*
C150.82752 (14)0.45026 (13)−0.09287 (9)0.0221 (4)
H150.86580.5027−0.11210.027*
C160.73263 (14)0.40062 (13)−0.14546 (9)0.0226 (4)
H160.70510.4193−0.20090.027*
C170.67777 (14)0.32337 (13)−0.11695 (9)0.0229 (4)
H170.61250.2892−0.15290.028*
C180.71826 (14)0.29622 (13)−0.03610 (9)0.0200 (4)
H180.68090.2427−0.01710.024*
C190.78158 (13)0.33436 (12)0.15313 (9)0.0152 (3)
C200.84763 (13)0.33288 (12)0.24544 (9)0.0165 (3)
C210.93020 (13)0.41240 (13)0.28752 (9)0.0185 (3)
C220.96876 (14)0.49707 (13)0.25033 (10)0.0226 (4)
H220.93790.50420.19340.027*
C231.04865 (15)0.56833 (14)0.29379 (10)0.0298 (4)
H231.07280.62290.26650.036*
C241.09580 (15)0.56233 (15)0.37820 (10)0.0330 (5)
H241.15070.61280.40800.040*
C251.06141 (15)0.48290 (15)0.41645 (10)0.0290 (4)
H251.09320.47840.47350.035*
C260.97938 (14)0.40671 (14)0.37352 (9)0.0213 (4)
C270.94584 (14)0.32554 (13)0.41524 (9)0.0231 (4)
H270.97720.32310.47240.028*
C280.86905 (14)0.25075 (14)0.37456 (9)0.0231 (4)
H280.84810.19560.40320.028*
C290.82034 (14)0.25491 (13)0.28971 (9)0.0197 (4)
H290.76690.20190.26230.024*
C300.71441 (13)0.43988 (13)0.12888 (9)0.0192 (4)
H30A0.76800.50040.14020.023*
H30B0.67160.43890.07020.023*
C310.63248 (13)0.45846 (13)0.17306 (9)0.0200 (4)
H31A0.67480.45980.23180.024*
H31B0.59560.52890.15730.024*
C320.45593 (14)0.39331 (16)0.07646 (9)0.0297 (4)
H32A0.40160.33440.06460.045*
H32B0.48850.39740.03420.045*
H32C0.41770.46070.07840.045*
C330.49847 (15)0.36798 (15)0.21797 (10)0.0299 (4)
H33A0.46470.43690.22280.045*
H33B0.55820.35060.26920.045*
H33C0.44060.31210.20460.045*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.02826 (10)0.01699 (10)0.03531 (11)−0.00165 (8)0.01222 (8)−0.00535 (8)
O10.0141 (6)0.0170 (6)0.0266 (6)−0.0019 (5)0.0043 (5)−0.0017 (5)
O20.0150 (6)0.0170 (6)0.0236 (6)−0.0014 (5)0.0094 (5)−0.0025 (5)
N10.0148 (7)0.0228 (8)0.0176 (6)0.0014 (6)0.0061 (5)−0.0020 (6)
C10.0155 (8)0.0185 (9)0.0117 (7)0.0017 (7)0.0060 (6)0.0009 (6)
C20.0150 (8)0.0199 (9)0.0157 (7)−0.0003 (7)0.0057 (6)−0.0008 (7)
C30.0185 (8)0.0170 (9)0.0116 (7)0.0018 (7)0.0060 (6)0.0012 (7)
C40.0162 (8)0.0166 (9)0.0206 (8)0.0018 (7)0.0058 (6)0.0029 (7)
C50.0239 (9)0.0169 (9)0.0158 (8)−0.0010 (7)0.0076 (7)−0.0016 (7)
C60.0244 (9)0.0187 (9)0.0182 (8)0.0065 (7)0.0104 (7)0.0020 (7)
C70.0154 (8)0.0238 (9)0.0183 (8)0.0043 (7)0.0070 (6)0.0031 (7)
C80.0187 (8)0.0179 (9)0.0102 (7)0.0029 (7)0.0059 (6)0.0027 (7)
C90.0120 (8)0.0212 (9)0.0169 (7)0.0003 (7)0.0052 (6)0.0023 (7)
C100.0166 (8)0.0186 (9)0.0129 (7)−0.0021 (7)0.0051 (6)0.0008 (7)
C110.0157 (8)0.0244 (10)0.0292 (9)−0.0039 (8)0.0018 (7)0.0036 (8)
C120.0142 (8)0.0151 (9)0.0163 (7)−0.0017 (7)0.0051 (6)−0.0014 (7)
C130.0174 (8)0.0137 (8)0.0179 (8)0.0033 (7)0.0089 (6)−0.0012 (7)
C140.0198 (9)0.0149 (8)0.0209 (8)−0.0005 (7)0.0074 (7)−0.0013 (7)
C150.0267 (9)0.0176 (9)0.0244 (9)0.0026 (8)0.0120 (7)0.0057 (7)
C160.0310 (10)0.0214 (9)0.0159 (8)0.0078 (8)0.0091 (7)0.0023 (7)
C170.0226 (9)0.0234 (10)0.0192 (8)0.0010 (7)0.0031 (7)−0.0030 (7)
C180.0205 (9)0.0192 (9)0.0213 (8)−0.0021 (7)0.0085 (7)−0.0009 (7)
C190.0158 (8)0.0127 (8)0.0178 (7)−0.0016 (7)0.0067 (6)−0.0012 (7)
C200.0172 (8)0.0155 (8)0.0189 (8)0.0036 (7)0.0090 (7)−0.0008 (7)
C210.0188 (9)0.0185 (9)0.0197 (8)0.0021 (7)0.0087 (7)−0.0028 (7)
C220.0264 (9)0.0194 (9)0.0233 (8)−0.0022 (8)0.0103 (7)−0.0045 (8)
C230.0333 (11)0.0245 (10)0.0347 (10)−0.0084 (9)0.0158 (8)−0.0072 (9)
C240.0290 (10)0.0348 (12)0.0334 (10)−0.0101 (9)0.0088 (8)−0.0138 (9)
C250.0246 (10)0.0361 (11)0.0233 (9)−0.0007 (9)0.0047 (7)−0.0083 (8)
C260.0189 (9)0.0233 (9)0.0222 (8)0.0039 (8)0.0079 (7)−0.0046 (7)
C270.0243 (9)0.0281 (10)0.0171 (8)0.0060 (8)0.0075 (7)−0.0008 (7)
C280.0290 (10)0.0224 (10)0.0219 (8)0.0057 (8)0.0139 (7)0.0062 (8)
C290.0212 (9)0.0169 (9)0.0225 (8)0.0019 (8)0.0095 (7)−0.0002 (7)
C300.0198 (9)0.0168 (9)0.0227 (8)0.0016 (7)0.0098 (7)0.0026 (7)
C310.0213 (9)0.0160 (9)0.0225 (8)0.0032 (7)0.0077 (7)−0.0014 (7)
C320.0234 (10)0.0404 (12)0.0210 (8)0.0028 (9)0.0026 (7)−0.0052 (8)
C330.0299 (10)0.0354 (11)0.0307 (10)−0.0008 (9)0.0185 (8)−0.0008 (9)

Geometric parameters (Å, °)

Br1—C51.9063 (16)C16—C171.389 (2)
O1—C101.3746 (18)C16—H160.9500
O1—C111.4285 (19)C17—C181.385 (2)
O2—C191.4235 (18)C17—H170.9500
O2—H20.8400C18—H180.9500
N1—C331.457 (2)C19—C301.547 (2)
N1—C321.4686 (19)C19—C201.554 (2)
N1—C311.473 (2)C20—C291.373 (2)
C1—C21.367 (2)C20—C211.446 (2)
C1—C101.440 (2)C21—C221.424 (2)
C1—C121.527 (2)C21—C261.432 (2)
C2—C31.417 (2)C22—C231.365 (2)
C2—H2A0.9500C22—H220.9500
C3—C41.420 (2)C23—C241.405 (2)
C3—C81.424 (2)C23—H230.9500
C4—C51.359 (2)C24—C251.361 (2)
C4—H40.9500C24—H240.9500
C5—C61.409 (2)C25—C261.418 (2)
C6—C71.359 (2)C25—H250.9500
C6—H60.9500C26—C271.410 (2)
C7—C81.414 (2)C27—C281.359 (2)
C7—H70.9500C27—H270.9500
C8—C91.411 (2)C28—C291.412 (2)
C9—C101.364 (2)C28—H280.9500
C9—H90.9500C29—H290.9500
C11—H11A0.9800C30—C311.529 (2)
C11—H11B0.9800C30—H30A0.9900
C11—H11C0.9800C30—H30B0.9900
C12—C131.532 (2)C31—H31A0.9900
C12—C191.548 (2)C31—H31B0.9900
C12—H121.0000C32—H32A0.9800
C13—C141.387 (2)C32—H32B0.9800
C13—C181.390 (2)C32—H32C0.9800
C14—C151.380 (2)C33—H33A0.9800
C14—H140.9500C33—H33B0.9800
C15—C161.383 (2)C33—H33C0.9800
C15—H150.9500
C10—O1—C11116.76 (12)C17—C18—H18119.6
C19—O2—H2109.5C13—C18—H18119.6
C33—N1—C32110.09 (13)O2—C19—C30107.83 (12)
C33—N1—C31110.41 (12)O2—C19—C12107.39 (12)
C32—N1—C31111.38 (13)C30—C19—C12111.50 (12)
C2—C1—C10117.52 (14)O2—C19—C20110.23 (12)
C2—C1—C12124.14 (14)C30—C19—C20109.96 (12)
C10—C1—C12117.89 (14)C12—C19—C20109.89 (12)
C1—C2—C3122.47 (15)C29—C20—C21118.51 (14)
C1—C2—H2A118.8C29—C20—C19117.48 (14)
C3—C2—H2A118.8C21—C20—C19123.89 (13)
C2—C3—C4122.25 (14)C22—C21—C26116.13 (14)
C2—C3—C8118.84 (14)C22—C21—C20125.29 (14)
C4—C3—C8118.87 (14)C26—C21—C20118.58 (14)
C5—C4—C3119.48 (15)C23—C22—C21122.18 (15)
C5—C4—H4120.3C23—C22—H22118.9
C3—C4—H4120.3C21—C22—H22118.9
C4—C5—C6122.41 (15)C22—C23—C24121.17 (17)
C4—C5—Br1120.34 (13)C22—C23—H23119.4
C6—C5—Br1117.25 (12)C24—C23—H23119.4
C7—C6—C5118.81 (15)C25—C24—C23118.78 (17)
C7—C6—H6120.6C25—C24—H24120.6
C5—C6—H6120.6C23—C24—H24120.6
C6—C7—C8121.50 (15)C24—C25—C26121.83 (16)
C6—C7—H7119.3C24—C25—H25119.1
C8—C7—H7119.3C26—C25—H25119.1
C9—C8—C7122.44 (14)C27—C26—C25120.21 (15)
C9—C8—C3118.64 (14)C27—C26—C21119.88 (15)
C7—C8—C3118.93 (15)C25—C26—C21119.91 (15)
C10—C9—C8120.90 (15)C28—C27—C26120.68 (15)
C10—C9—H9119.5C28—C27—H27119.7
C8—C9—H9119.5C26—C27—H27119.7
C9—C10—O1123.80 (14)C27—C28—C29120.08 (15)
C9—C10—C1121.41 (15)C27—C28—H28120.0
O1—C10—C1114.79 (13)C29—C28—H28120.0
O1—C11—H11A109.5C20—C29—C28122.26 (15)
O1—C11—H11B109.5C20—C29—H29118.9
H11A—C11—H11B109.5C28—C29—H29118.9
O1—C11—H11C109.5C31—C30—C19113.34 (13)
H11A—C11—H11C109.5C31—C30—H30A108.9
H11B—C11—H11C109.5C19—C30—H30A108.9
C1—C12—C13108.90 (12)C31—C30—H30B108.9
C1—C12—C19116.47 (12)C19—C30—H30B108.9
C13—C12—C19113.99 (13)H30A—C30—H30B107.7
C1—C12—H12105.5N1—C31—C30111.68 (13)
C13—C12—H12105.5N1—C31—H31A109.3
C19—C12—H12105.5C30—C31—H31A109.3
C14—C13—C18118.16 (14)N1—C31—H31B109.3
C14—C13—C12117.94 (14)C30—C31—H31B109.3
C18—C13—C12123.88 (14)H31A—C31—H31B107.9
C15—C14—C13121.63 (15)N1—C32—H32A109.5
C15—C14—H14119.2N1—C32—H32B109.5
C13—C14—H14119.2H32A—C32—H32B109.5
C14—C15—C16119.64 (15)N1—C32—H32C109.5
C14—C15—H15120.2H32A—C32—H32C109.5
C16—C15—H15120.2H32B—C32—H32C109.5
C15—C16—C17119.78 (15)N1—C33—H33A109.5
C15—C16—H16120.1N1—C33—H33B109.5
C17—C16—H16120.1H33A—C33—H33B109.5
C18—C17—C16119.97 (15)N1—C33—H33C109.5
C18—C17—H17120.0H33A—C33—H33C109.5
C16—C17—H17120.0H33B—C33—H33C109.5
C17—C18—C13120.81 (15)
C10—C1—C2—C3−2.8 (2)C14—C13—C18—C17−0.6 (2)
C12—C1—C2—C3169.34 (13)C12—C13—C18—C17−178.95 (15)
C1—C2—C3—C4−179.16 (14)C1—C12—C19—O2−54.08 (16)
C1—C2—C3—C8−1.3 (2)C13—C12—C19—O274.07 (16)
C2—C3—C4—C5177.46 (14)C1—C12—C19—C30−171.99 (12)
C8—C3—C4—C5−0.4 (2)C13—C12—C19—C30−43.84 (17)
C3—C4—C5—C6−0.4 (2)C1—C12—C19—C2065.83 (17)
C3—C4—C5—Br1−179.92 (10)C13—C12—C19—C20−166.02 (12)
C4—C5—C6—C70.7 (2)O2—C19—C20—C29−1.59 (19)
Br1—C5—C6—C7−179.83 (11)C30—C19—C20—C29117.16 (15)
C5—C6—C7—C80.0 (2)C12—C19—C20—C29−119.75 (15)
C6—C7—C8—C9178.93 (14)O2—C19—C20—C21−177.43 (13)
C6—C7—C8—C3−0.8 (2)C30—C19—C20—C21−58.69 (18)
C2—C3—C8—C93.3 (2)C12—C19—C20—C2164.40 (18)
C4—C3—C8—C9−178.72 (13)C29—C20—C21—C22178.94 (15)
C2—C3—C8—C7−176.94 (13)C19—C20—C21—C22−5.3 (2)
C4—C3—C8—C71.0 (2)C29—C20—C21—C26−0.4 (2)
C7—C8—C9—C10179.15 (14)C19—C20—C21—C26175.44 (14)
C3—C8—C9—C10−1.1 (2)C26—C21—C22—C230.6 (2)
C8—C9—C10—O1177.60 (13)C20—C21—C22—C23−178.76 (16)
C8—C9—C10—C1−3.2 (2)C21—C22—C23—C24−1.0 (3)
C11—O1—C10—C9−4.5 (2)C22—C23—C24—C250.8 (3)
C11—O1—C10—C1176.23 (13)C23—C24—C25—C26−0.2 (3)
C2—C1—C10—C95.1 (2)C24—C25—C26—C27−179.99 (17)
C12—C1—C10—C9−167.56 (13)C24—C25—C26—C21−0.2 (3)
C2—C1—C10—O1−175.57 (12)C22—C21—C26—C27179.84 (15)
C12—C1—C10—O111.76 (19)C20—C21—C26—C27−0.8 (2)
C2—C1—C12—C13−69.92 (18)C22—C21—C26—C250.0 (2)
C10—C1—C12—C13102.23 (15)C20—C21—C26—C25179.38 (15)
C2—C1—C12—C1960.67 (19)C25—C26—C27—C28−178.59 (16)
C10—C1—C12—C19−127.18 (15)C21—C26—C27—C281.6 (2)
C1—C12—C13—C14−105.02 (16)C26—C27—C28—C29−1.2 (2)
C19—C12—C13—C14123.06 (15)C21—C20—C29—C280.8 (2)
C1—C12—C13—C1873.29 (18)C19—C20—C29—C28−175.28 (14)
C19—C12—C13—C18−58.6 (2)C27—C28—C29—C200.0 (2)
C18—C13—C14—C150.0 (2)O2—C19—C30—C3162.77 (16)
C12—C13—C14—C15178.37 (14)C12—C19—C30—C31−179.59 (13)
C13—C14—C15—C160.6 (2)C20—C19—C30—C31−57.44 (17)
C14—C15—C16—C17−0.6 (2)C33—N1—C31—C30157.51 (13)
C15—C16—C17—C18−0.1 (2)C32—N1—C31—C30−79.86 (16)
C16—C17—C18—C130.7 (2)C19—C30—C31—N1−62.24 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···N10.841.932.6988 (17)151

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2176).

References

  • Andries, K., Verhasselt, P. & Guillemont, J. (2005). Science, 307, 223–227. [PubMed]
  • Cohen, J. (2004). Science 306, 1872. [PubMed]
  • Guillemont, J., Van Gestel, J., Venet, M., Poignet, H., Decrane, L. & Vernier, D. (2004). WO Patent, WO2004011436.
  • Rigaku/MSC (2005). CrystalClear Rigaku/MSC, The Woodlands, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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