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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1571.
Published online 2010 June 5. doi:  10.1107/S160053681001891X
PMCID: PMC3006773

(1R*,2R*)-1-(4-Chloro­phen­yl)-4-dimethyl­amino-1-(3-meth­oxy-2-naphth­yl)-2-(1-naphth­yl)butan-2-ol

Abstract

In the title compound, C33H32ClNO2, the benzene ring is oriented at dihedral angles of 6.23 (5) and 66.44 (5)° with respect to the two naphthalene ring systems. An intra­molecular O—H(...)N hydrogen bond between the hydr­oxy H atom and the amine N atom generates an S(6) ring.

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-o1571-scheme1.jpg

Experimental

Crystal data

  • C33H32ClNO2
  • M r = 510.05
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1571-efi1.jpg
  • a = 18.712 (5) Å
  • b = 9.135 (2) Å
  • c = 16.369 (4) Å
  • β = 111.991 (4)°
  • V = 2594.2 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.18 mm−1
  • T = 116 K
  • 0.20 × 0.16 × 0.12 mm

Data collection

  • Rigaku Saturn CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.965, T max = 0.979
  • 18901 measured reflections
  • 4573 independent reflections
  • 3918 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.099
  • S = 1.09
  • 4573 reflections
  • 338 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.31 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: CrystalStructure (Rigaku/MSC, 2005 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001891X/hb5430sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001891X/hb5430Isup2.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,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 et al. 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 benzene ring (C13—C18) amount to 6.232 (46)° whereas the other naphthalene ring (C2—C10) is oriented with respect to the benzene ring at a dihedral angle of 66.438 (51)°. In the structure an intramolecular O—H···N hydrogen bond is found (Tab. 1).

Experimental

n-BuLi (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 2-(4-chlorobenzyl)-3-methoxynaphthalene (2.59 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 colourless prisms of (I) 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.
Ellipsoid plot

Crystal data

C33H32ClNO2F(000) = 1080
Mr = 510.05Dx = 1.306 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8940 reflections
a = 18.712 (5) Åθ = 2.2–27.9°
b = 9.135 (2) ŵ = 0.18 mm1
c = 16.369 (4) ÅT = 116 K
β = 111.991 (4)°Prism, colorless
V = 2594.2 (11) Å30.20 × 0.16 × 0.12 mm
Z = 4

Data collection

Rigaku Saturn CCD diffractometer4573 independent reflections
Radiation source: rotating anode3918 reflections with I > 2σ(I)
multilayerRint = 0.032
Detector resolution: 14.63 pixels mm-1θmax = 25.0°, θmin = 2.4°
ω and [var phi] scansh = −19→22
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −10→10
Tmin = 0.965, Tmax = 0.979l = −19→19
18901 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0587P)2 + 0.0772P] where P = (Fo2 + 2Fc2)/3
4573 reflections(Δ/σ)max = 0.001
338 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.31 e Å3

Special details

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 > 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
Cl10.08594 (2)−0.07359 (5)0.46621 (2)0.03327 (14)
O10.37601 (6)0.47214 (13)0.67039 (6)0.0280 (3)
O20.15042 (6)0.45626 (11)0.76790 (6)0.0224 (2)
H20.10370.46740.75200.034*
N10.00317 (7)0.54248 (15)0.68199 (8)0.0262 (3)
C10.43816 (10)0.55500 (19)0.66354 (11)0.0350 (4)
H1A0.44970.63570.70400.053*
H1B0.42380.59140.60450.053*
H1C0.48280.49360.67750.053*
C20.38276 (8)0.42853 (16)0.75343 (9)0.0213 (3)
C30.45183 (8)0.39820 (17)0.81939 (9)0.0234 (3)
H30.49710.40670.80880.028*
C40.45519 (8)0.35391 (16)0.90395 (9)0.0220 (3)
C50.52573 (9)0.32564 (17)0.97478 (10)0.0269 (4)
H50.57190.33350.96600.032*
C60.52683 (9)0.28711 (18)1.05574 (10)0.0294 (4)
H60.57360.26861.10150.035*
C70.45778 (9)0.27531 (17)1.07038 (10)0.0287 (4)
H70.45900.24991.12590.034*
C80.38864 (9)0.30102 (17)1.00330 (10)0.0252 (4)
H80.34320.29181.01360.030*
C90.38510 (8)0.34155 (16)0.91827 (9)0.0212 (3)
C100.31462 (8)0.37265 (16)0.84820 (9)0.0211 (3)
H100.26880.36360.85770.025*
C110.31159 (8)0.41579 (15)0.76655 (9)0.0192 (3)
C120.23748 (8)0.45229 (16)0.69006 (9)0.0191 (3)
H120.25300.51430.65070.023*
C130.20123 (8)0.31600 (16)0.63590 (9)0.0190 (3)
C140.17019 (8)0.20240 (17)0.66875 (9)0.0222 (3)
H140.17300.20700.72660.027*
C150.13521 (8)0.08287 (17)0.61745 (9)0.0237 (3)
H150.11400.00870.64020.028*
C160.13221 (8)0.07529 (17)0.53164 (9)0.0227 (3)
C170.16557 (9)0.18162 (17)0.49810 (9)0.0250 (4)
H170.16550.17350.44140.030*
C180.19958 (8)0.30198 (16)0.55077 (9)0.0225 (3)
H180.22170.37480.52820.027*
C190.17914 (8)0.54677 (16)0.71574 (9)0.0205 (3)
C200.21941 (8)0.68257 (16)0.76984 (9)0.0208 (3)
C210.26013 (8)0.79135 (16)0.73961 (9)0.0209 (3)
C220.26584 (8)0.79312 (16)0.65518 (9)0.0214 (3)
H220.24140.71990.61490.026*
C230.30608 (8)0.89908 (17)0.63137 (10)0.0247 (4)
H230.30790.89690.57540.030*
C240.34450 (9)1.01083 (17)0.69010 (11)0.0281 (4)
H240.37251.08130.67380.034*
C250.34029 (8)1.01492 (18)0.77106 (10)0.0271 (4)
H250.36581.08910.81000.033*
C260.29797 (8)0.90910 (17)0.79797 (9)0.0218 (3)
C270.29246 (9)0.92087 (17)0.88158 (10)0.0278 (4)
H270.31650.99790.91890.033*
C280.25203 (9)0.81963 (18)0.90722 (10)0.0293 (4)
H280.24750.82890.96170.035*
C290.21699 (9)0.70118 (17)0.85237 (9)0.0249 (4)
H290.19100.63210.87250.030*
C300.11066 (8)0.59297 (17)0.63159 (9)0.0227 (3)
H30A0.12860.66590.60060.027*
H30B0.09360.50850.59330.027*
C310.04188 (9)0.65525 (17)0.64869 (10)0.0265 (4)
H31A0.05930.73390.69140.032*
H31B0.00530.69590.59440.032*
C32−0.04747 (10)0.6089 (2)0.72092 (11)0.0421 (5)
H32A−0.08680.66450.67690.063*
H32B−0.01800.67250.76820.063*
H32C−0.07100.53360.74330.063*
C33−0.04136 (10)0.44129 (19)0.61219 (11)0.0365 (4)
H33A−0.06700.37140.63550.055*
H33B−0.00730.39100.59000.055*
H33C−0.07890.49510.56530.055*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0334 (2)0.0323 (3)0.0330 (2)−0.00749 (18)0.01111 (19)−0.01273 (17)
O10.0230 (6)0.0368 (7)0.0278 (6)−0.0038 (5)0.0136 (5)0.0018 (5)
O20.0187 (5)0.0247 (6)0.0265 (5)0.0016 (5)0.0115 (5)0.0046 (4)
N10.0195 (7)0.0352 (8)0.0249 (7)0.0038 (6)0.0096 (6)0.0013 (6)
C10.0330 (10)0.0371 (11)0.0395 (9)−0.0092 (8)0.0187 (8)0.0022 (8)
C20.0217 (8)0.0184 (9)0.0253 (8)−0.0019 (6)0.0105 (7)−0.0033 (6)
C30.0173 (8)0.0223 (9)0.0327 (8)−0.0017 (6)0.0119 (7)−0.0057 (7)
C40.0217 (8)0.0162 (8)0.0275 (8)0.0002 (6)0.0085 (7)−0.0060 (6)
C50.0209 (8)0.0237 (9)0.0357 (9)0.0008 (7)0.0101 (7)−0.0085 (7)
C60.0241 (9)0.0263 (10)0.0287 (8)0.0061 (7)−0.0006 (7)−0.0041 (7)
C70.0333 (9)0.0247 (9)0.0253 (8)0.0036 (7)0.0077 (7)0.0000 (7)
C80.0251 (8)0.0233 (9)0.0281 (8)−0.0012 (7)0.0109 (7)−0.0013 (7)
C90.0215 (8)0.0157 (8)0.0254 (8)−0.0008 (6)0.0076 (7)−0.0036 (6)
C100.0187 (8)0.0185 (8)0.0266 (8)−0.0007 (6)0.0092 (7)−0.0013 (6)
C110.0185 (8)0.0147 (8)0.0248 (7)−0.0008 (6)0.0086 (6)−0.0036 (6)
C120.0183 (8)0.0189 (8)0.0219 (7)−0.0003 (6)0.0094 (6)0.0019 (6)
C130.0142 (7)0.0201 (8)0.0217 (7)0.0034 (6)0.0057 (6)0.0015 (6)
C140.0213 (8)0.0248 (9)0.0213 (7)0.0007 (6)0.0090 (6)−0.0001 (6)
C150.0218 (8)0.0218 (9)0.0299 (8)−0.0020 (6)0.0127 (7)0.0004 (6)
C160.0167 (8)0.0240 (9)0.0238 (7)0.0025 (6)0.0034 (6)−0.0049 (6)
C170.0265 (9)0.0279 (9)0.0195 (7)0.0046 (7)0.0072 (7)0.0009 (6)
C180.0225 (8)0.0213 (9)0.0251 (8)0.0030 (6)0.0104 (7)0.0043 (6)
C190.0214 (8)0.0196 (8)0.0231 (7)0.0004 (6)0.0111 (6)0.0028 (6)
C200.0187 (8)0.0212 (9)0.0220 (7)0.0065 (6)0.0071 (6)0.0023 (6)
C210.0186 (8)0.0187 (8)0.0243 (7)0.0052 (6)0.0069 (6)0.0016 (6)
C220.0217 (8)0.0187 (9)0.0240 (7)0.0034 (6)0.0088 (6)0.0002 (6)
C230.0230 (8)0.0249 (9)0.0282 (8)0.0027 (7)0.0118 (7)0.0024 (7)
C240.0242 (9)0.0211 (9)0.0423 (9)−0.0001 (7)0.0163 (7)0.0043 (7)
C250.0210 (8)0.0211 (9)0.0350 (9)0.0009 (7)0.0056 (7)−0.0028 (7)
C260.0177 (8)0.0197 (9)0.0248 (7)0.0056 (6)0.0044 (6)0.0010 (6)
C270.0298 (9)0.0235 (9)0.0263 (8)0.0047 (7)0.0062 (7)−0.0050 (7)
C280.0363 (10)0.0305 (10)0.0214 (8)0.0076 (7)0.0111 (7)−0.0020 (7)
C290.0284 (9)0.0239 (9)0.0262 (8)0.0035 (7)0.0146 (7)0.0021 (7)
C300.0215 (8)0.0231 (9)0.0243 (7)0.0002 (6)0.0097 (7)0.0034 (6)
C310.0235 (8)0.0235 (9)0.0292 (8)0.0051 (7)0.0061 (7)−0.0004 (7)
C320.0301 (10)0.0687 (14)0.0294 (9)0.0167 (9)0.0133 (8)0.0060 (9)
C330.0287 (9)0.0394 (11)0.0402 (10)−0.0052 (8)0.0116 (8)−0.0022 (8)

Geometric parameters (Å, °)

Cl1—C161.7469 (15)C15—H150.9300
O1—C21.3761 (17)C16—C171.375 (2)
O1—C11.4268 (18)C17—C181.395 (2)
O2—C191.4299 (17)C17—H170.9300
O2—H20.8200C18—H180.9300
N1—C321.4576 (19)C19—C201.546 (2)
N1—C331.463 (2)C19—C301.548 (2)
N1—C311.476 (2)C20—C291.379 (2)
C1—H1A0.9600C20—C211.447 (2)
C1—H1B0.9600C21—C221.4256 (19)
C1—H1C0.9600C21—C261.437 (2)
C2—C31.367 (2)C22—C231.369 (2)
C2—C111.431 (2)C22—H220.9300
C3—C41.421 (2)C23—C241.402 (2)
C3—H30.9300C23—H230.9300
C4—C51.417 (2)C24—C251.357 (2)
C4—C91.421 (2)C24—H240.9300
C5—C61.364 (2)C25—C261.420 (2)
C5—H50.9300C25—H250.9300
C6—C71.404 (2)C26—C271.415 (2)
C6—H60.9300C27—C281.357 (2)
C7—C81.368 (2)C27—H270.9300
C7—H70.9300C28—C291.402 (2)
C8—C91.418 (2)C28—H280.9300
C8—H80.9300C29—H290.9300
C9—C101.415 (2)C30—C311.526 (2)
C10—C111.374 (2)C30—H30A0.9700
C10—H100.9300C30—H30B0.9700
C11—C121.517 (2)C31—H31A0.9700
C12—C131.532 (2)C31—H31B0.9700
C12—C191.567 (2)C32—H32A0.9600
C12—H120.9800C32—H32B0.9600
C13—C181.3881 (19)C32—H32C0.9600
C13—C141.392 (2)C33—H33A0.9600
C14—C151.383 (2)C33—H33B0.9600
C14—H140.9300C33—H33C0.9600
C15—C161.386 (2)
C2—O1—C1117.08 (12)C13—C18—H18119.1
C19—O2—H2109.5C17—C18—H18119.1
C32—N1—C33109.34 (13)O2—C19—C20109.47 (11)
C32—N1—C31111.10 (14)O2—C19—C30108.55 (12)
C33—N1—C31111.54 (12)C20—C19—C30110.76 (12)
O1—C1—H1A109.5O2—C19—C12107.27 (11)
O1—C1—H1B109.5C20—C19—C12110.87 (12)
H1A—C1—H1B109.5C30—C19—C12109.82 (11)
O1—C1—H1C109.5C29—C20—C21117.70 (14)
H1A—C1—H1C109.5C29—C20—C19118.17 (13)
H1B—C1—H1C109.5C21—C20—C19124.12 (12)
C3—C2—O1123.29 (13)C22—C21—C26116.03 (13)
C3—C2—C11121.53 (13)C22—C21—C20125.40 (13)
O1—C2—C11115.18 (12)C26—C21—C20118.56 (13)
C2—C3—C4120.75 (13)C23—C22—C21122.18 (14)
C2—C3—H3119.6C23—C22—H22118.9
C4—C3—H3119.6C21—C22—H22118.9
C5—C4—C9119.03 (13)C22—C23—C24120.99 (14)
C5—C4—C3122.48 (14)C22—C23—H23119.5
C9—C4—C3118.46 (13)C24—C23—H23119.5
C6—C5—C4120.84 (14)C25—C24—C23119.16 (15)
C6—C5—H5119.6C25—C24—H24120.4
C4—C5—H5119.6C23—C24—H24120.4
C5—C6—C7120.38 (14)C24—C25—C26121.81 (15)
C5—C6—H6119.8C24—C25—H25119.1
C7—C6—H6119.8C26—C25—H25119.1
C8—C7—C6120.28 (15)C27—C26—C25119.96 (14)
C8—C7—H7119.9C27—C26—C21120.26 (14)
C6—C7—H7119.9C25—C26—C21119.78 (13)
C7—C8—C9121.03 (15)C28—C27—C26119.90 (15)
C7—C8—H8119.5C28—C27—H27120.0
C9—C8—H8119.5C26—C27—H27120.0
C10—C9—C8122.33 (14)C27—C28—C29120.60 (14)
C10—C9—C4119.22 (13)C27—C28—H28119.7
C8—C9—C4118.43 (13)C29—C28—H28119.7
C11—C10—C9122.17 (14)C20—C29—C28122.92 (14)
C11—C10—H10118.9C20—C29—H29118.5
C9—C10—H10118.9C28—C29—H29118.5
C10—C11—C2117.87 (13)C31—C30—C19114.37 (12)
C10—C11—C12123.90 (13)C31—C30—H30A108.7
C2—C11—C12118.22 (12)C19—C30—H30A108.7
C11—C12—C13111.65 (12)C31—C30—H30B108.7
C11—C12—C19114.39 (12)C19—C30—H30B108.7
C13—C12—C19113.64 (11)H30A—C30—H30B107.6
C11—C12—H12105.4N1—C31—C30111.82 (13)
C13—C12—H12105.4N1—C31—H31A109.3
C19—C12—H12105.4C30—C31—H31A109.3
C18—C13—C14117.61 (14)N1—C31—H31B109.3
C18—C13—C12119.65 (13)C30—C31—H31B109.3
C14—C13—C12122.73 (12)H31A—C31—H31B107.9
C15—C14—C13121.66 (13)N1—C32—H32A109.5
C15—C14—H14119.2N1—C32—H32B109.5
C13—C14—H14119.2H32A—C32—H32B109.5
C14—C15—C16119.00 (14)N1—C32—H32C109.5
C14—C15—H15120.5H32A—C32—H32C109.5
C16—C15—H15120.5H32B—C32—H32C109.5
C17—C16—C15121.13 (14)N1—C33—H33A109.5
C17—C16—Cl1119.99 (11)N1—C33—H33B109.5
C15—C16—Cl1118.87 (12)H33A—C33—H33B109.5
C16—C17—C18118.69 (13)N1—C33—H33C109.5
C16—C17—H17120.7H33A—C33—H33C109.5
C18—C17—H17120.7H33B—C33—H33C109.5
C13—C18—C17121.78 (14)
C1—O1—C2—C3−31.0 (2)C12—C13—C18—C17−178.43 (13)
C1—O1—C2—C11149.34 (14)C16—C17—C18—C130.7 (2)
O1—C2—C3—C4179.86 (13)C11—C12—C19—O2−69.07 (15)
C11—C2—C3—C4−0.5 (2)C13—C12—C19—O260.76 (15)
C2—C3—C4—C5−178.10 (14)C11—C12—C19—C2050.41 (16)
C2—C3—C4—C90.1 (2)C13—C12—C19—C20−179.75 (11)
C9—C4—C5—C60.0 (2)C11—C12—C19—C30173.14 (12)
C3—C4—C5—C6178.22 (15)C13—C12—C19—C30−57.03 (15)
C4—C5—C6—C7−0.2 (2)O2—C19—C20—C29−4.46 (18)
C5—C6—C7—C80.6 (2)C30—C19—C20—C29115.19 (14)
C6—C7—C8—C9−0.7 (2)C12—C19—C20—C29−122.62 (14)
C7—C8—C9—C10−178.28 (15)O2—C19—C20—C21175.08 (12)
C7—C8—C9—C40.5 (2)C30—C19—C20—C21−65.26 (17)
C5—C4—C9—C10178.70 (14)C12—C19—C20—C2156.92 (17)
C3—C4—C9—C100.4 (2)C29—C20—C21—C22−177.28 (14)
C5—C4—C9—C8−0.1 (2)C19—C20—C21—C223.2 (2)
C3—C4—C9—C8−178.39 (14)C29—C20—C21—C262.2 (2)
C8—C9—C10—C11178.18 (14)C19—C20—C21—C26−177.31 (12)
C4—C9—C10—C11−0.6 (2)C26—C21—C22—C231.1 (2)
C9—C10—C11—C20.2 (2)C20—C21—C22—C23−179.36 (14)
C9—C10—C11—C12−179.08 (13)C21—C22—C23—C240.7 (2)
C3—C2—C11—C100.4 (2)C22—C23—C24—C25−1.3 (2)
O1—C2—C11—C10−179.99 (13)C23—C24—C25—C260.0 (2)
C3—C2—C11—C12179.68 (13)C24—C25—C26—C27−177.40 (14)
O1—C2—C11—C12−0.69 (19)C24—C25—C26—C211.9 (2)
C10—C11—C12—C13−87.94 (17)C22—C21—C26—C27176.94 (13)
C2—C11—C12—C1392.80 (15)C20—C21—C26—C27−2.6 (2)
C10—C11—C12—C1942.9 (2)C22—C21—C26—C25−2.3 (2)
C2—C11—C12—C19−136.39 (13)C20—C21—C26—C25178.11 (13)
C11—C12—C13—C18−111.46 (15)C25—C26—C27—C28−179.97 (14)
C19—C12—C13—C18117.34 (14)C21—C26—C27—C280.8 (2)
C11—C12—C13—C1467.65 (17)C26—C27—C28—C291.5 (2)
C19—C12—C13—C14−63.55 (18)C21—C20—C29—C28−0.1 (2)
C18—C13—C14—C15−3.3 (2)C19—C20—C29—C28179.50 (13)
C12—C13—C14—C15177.58 (13)C27—C28—C29—C20−1.9 (2)
C13—C14—C15—C161.0 (2)O2—C19—C30—C3149.88 (17)
C14—C15—C16—C172.2 (2)C20—C19—C30—C31−70.33 (16)
C14—C15—C16—Cl1−178.46 (11)C12—C19—C30—C31166.88 (13)
C15—C16—C17—C18−3.1 (2)C32—N1—C31—C30164.04 (13)
Cl1—C16—C17—C18177.63 (11)C33—N1—C31—C30−73.70 (16)
C14—C13—C18—C172.4 (2)C19—C30—C31—N1−68.12 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.932.6995 (17)157

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5430).

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, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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