PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2984–o2985.
Published online 2010 October 30. doi:  10.1107/S1600536810042960
PMCID: PMC3009334

1-Benz­yloxy-4-(2-nitro­ethen­yl)benzene

Abstract

The title compound, C15H13NO3, crystallizes with three independent mol­ecules per asymmetric unit (Z′ = 3). One of these mol­ecules is found to have a configuration with a greater twist between its two aromatic rings than the other two [compare 70.26 (13) and 72.31 (12)° with 84.22 (12)°]. There are also differences in the number and nature of the weak inter­molecular C—H(...)O contacts formed by each of the three mol­ecules.

Related literature

For discussion of C—H(...)O contacts in related derivatives, see: Gerkin (1999 [triangle]). For other related structures, see: Gao et al. (2008 [triangle]); Stomberg & Lundquist (1994 [triangle]); Wang et al. (2007 [triangle]); Zheng et al. (2008 [triangle]); Kennedy et al. (2010 [triangle]). On the design of new small mol­ecules that target HIV-1 binding sites, see: Younis et al. (2010 [triangle]); Hunter et al. (2008 [triangle]); Jones et al. (2006 [triangle]). For background to the anti­retroviral treatment programme for AIDS, see: UNAIDS/WHO (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2984-scheme1.jpg

Experimental

Crystal data

  • C15H13NO3
  • M r = 255.26
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2984-efi1.jpg
  • a = 9.9522 (8) Å
  • b = 14.0456 (13) Å
  • c = 14.2506 (10) Å
  • α = 74.416 (5)°
  • β = 84.188 (5)°
  • γ = 80.888 (4)°
  • V = 1891.0 (3) Å3
  • Z = 6
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 120 K
  • 0.12 × 0.10 × 0.05 mm

Data collection

  • Bruker–Nonius APEXII CCD diffractometer
  • 25754 measured reflections
  • 7366 independent reflections
  • 4735 reflections with I > 2σ(I)
  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.088
  • wR(F 2) = 0.170
  • S = 1.14
  • 7366 reflections
  • 514 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: COLLECT (Hooft, 1998 [triangle]); cell refinement: DENZO (Otwinowski & Minor, 1997 [triangle]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042960/si2304sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042960/si2304Isup2.hkl

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

Acknowledgments

We are grateful to the National Crystallography Service, University of Southampton, for data collection. MOO also thanks the Commonwealth Scholarship Commission and the British Council for funding and Moi University for sabatical leave.

supplementary crystallographic information

Comment

One of the most serious threats to human health today is acquired immunodeficiency syndrome, AIDS (UNAIDS/WHO, 2009). Most drugs used in AIDS treatment target the HIV-1 reverse transcriptase (RT). A class of compounds known as non-nucleoside reverse transcriptase inhibitors (NNRTIs) inhibits the ability of RT to transcribe by altering its structural and dynamic properties (Jones et al., 2006). In our research, (Hunter et al., 2008; Younis et al., 2010) N-[4-(2-prop-2-ynyloxyphenyl)ethyl]-N'-[2-(5-bromopyridyl)]thiourea, a phenylethylthiazolylthiourea analogue was the target NNRTI compound, using 4-hydroxy benzaldehyde as the starting material. In this paper, the crystal structure of a synthon of the target compound, namely 2-(4-benzyloxyphenyl)-1-nitroethene, is described as determined by x-ray diffraction.

The sample was recrystallized several times, and data collected from numerous crystals. Non-single-crystal samples were common and data quality tended to be low, however all data collections were consistant with that of the best quality structure found, as described below. The title compound was found to exist as discrete molecules (Figure 1), although there are some non-classical hydrogen bonding C—H···O interactions involving nitro and ether O atoms and H atoms from sp2 aromatic and vinylic C atoms, see Table 1. Unlike related compounds, the CH2 atoms do not act as hydrogen bond donors (Gerkin, 1999; Kennedy et al., 2010). The asymmetric unit contains three independent molecules (Figure 2). Two have similar configurations but the third, that with C atoms numbered C16 through to C30, is somewhat more twisted. This is shown by the angle between the least squares planes of the aromatic rings (compare 70.26 (13) and 72.31 (12) with 84.22 (12) °). Related vinyl substituted benzyloxyphenyl species are known to have both twisted (Wang et al., 2007; Zheng et al., 2008) and planar conformations (Gao et al., 2008; Stomberg & Lundquist, 1994) but in all cases, including the title complex, the vinyl group is coplanar with the attached aromatic ring. The three crystallographically independent molecules also differ from one another in the nature and number of their intermolecular contacts, Table 1. However, bond lengths and angles are in good agreement between the different configurations and with the related literature species.

Experimental

All reactions in the preparation of 2-(4-benzyloxyphenyl)-1-nitroethene were performed under an atmosphere of nitrogen gas. 3.85 g, (18.16 mmol) of 4-benzyloxybenzaldehyde and 1.22 g of ammonium acetate (15.80 mmol) in nitromethane (100 ml) were heated at 343 K for 9 h. The solution was cooled and diluted with dichloromethane (54 ml), then washed with two 200 ml portions of saturated sodium chloride solution and then washed with of 200 ml distilled water. The resulting solution was dried over anhydrous magnesium sulfate and the solvent evaporated to dryness under reduced pressure. Recrystallization of the crude produce from ethanol gave yellow crystals (3.84 g, 83%), Mp: 387–388 K.

Refinement

All H atoms were placed in calculated positions and refined in riding modes with Uiso(H) = 1.2Ueq(C). C—H distances 0.95 and 0.99 Å for CH and CH2 respectively.

Figures

Fig. 1.
The molecular structure of one configuration of 2-(4-benzyloxyphenyl)-1-nitroethene showing 50% probability displacement ellipsoids.
Fig. 2.
Contents of the asymmetric unit.

Crystal data

C15H13NO3Z = 6
Mr = 255.26F(000) = 804
Triclinic, P1Dx = 1.345 Mg m3
a = 9.9522 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.0456 (13) ÅCell parameters from 78718 reflections
c = 14.2506 (10) Åθ = 2.9–27.5°
α = 74.416 (5)°µ = 0.09 mm1
β = 84.188 (5)°T = 120 K
γ = 80.888 (4)°Cut slab, pale yellow
V = 1891.0 (3) Å30.12 × 0.10 × 0.05 mm

Data collection

Bruker–Nonius APEXII CCD diffractometer4735 reflections with I > 2σ(I)
Radiation source: Bruker-Nonius FR591 rotating anodeRint = 0.063
10cm confocal mirrorsθmax = 26.0°, θmin = 3.0°
Detector resolution: 4096x4096pixels / 62x62mm pixels mm-1h = −12→12
[var phi] & ω scansk = −17→17
25754 measured reflectionsl = −17→17
7366 independent 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)] = 0.088Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.14w = 1/[σ2(Fo2) + (0.0086P)2 + 3.8491P] where P = (Fo2 + 2Fc2)/3
7366 reflections(Δ/σ)max < 0.001
514 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.28 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
O10.9330 (2)0.37883 (19)0.37919 (17)0.0306 (6)
O21.0417 (3)−0.0863 (2)0.9274 (2)0.0468 (8)
O30.8252 (3)−0.0489 (2)0.9037 (2)0.0426 (7)
O40.7595 (2)0.6336 (2)0.93137 (18)0.0337 (6)
O50.8521 (3)1.0608 (2)0.40189 (19)0.0382 (7)
O60.6349 (3)1.1069 (2)0.3947 (2)0.0458 (8)
O70.4798 (2)0.3091 (2)0.71568 (17)0.0328 (6)
O80.6922 (3)−0.0535 (2)1.2632 (2)0.0462 (8)
O90.4823 (3)−0.0710 (2)1.31177 (19)0.0412 (7)
N10.9451 (3)−0.0400 (2)0.8780 (2)0.0342 (8)
N20.7348 (3)1.0530 (2)0.4349 (2)0.0320 (7)
N30.5696 (3)−0.0360 (2)1.2495 (2)0.0322 (8)
C10.9316 (4)0.3020 (3)0.4612 (2)0.0274 (8)
C21.0458 (3)0.2566 (3)0.5139 (3)0.0271 (8)
H21.13260.27690.49150.033*
C31.0318 (4)0.1819 (3)0.5989 (3)0.0285 (8)
H31.10990.15070.63430.034*
C40.9047 (4)0.1516 (3)0.6337 (3)0.0271 (8)
C50.7925 (4)0.1967 (3)0.5792 (3)0.0309 (9)
H50.70560.17660.60140.037*
C60.8055 (4)0.2702 (3)0.4936 (3)0.0292 (8)
H60.72820.29920.45670.035*
C70.8843 (4)0.0774 (3)0.7258 (3)0.0279 (8)
H70.79420.06190.74380.034*
C80.9796 (4)0.0295 (3)0.7866 (3)0.0319 (9)
H81.07160.04080.77000.038*
C91.0559 (4)0.4252 (3)0.3534 (3)0.0299 (9)
H9A1.13050.37880.33160.036*
H9B1.08460.44230.41070.036*
C101.0263 (3)0.5182 (3)0.2724 (3)0.0276 (8)
C110.9907 (4)0.5121 (3)0.1823 (3)0.0322 (9)
H110.98360.44900.17230.039*
C120.9657 (4)0.5980 (3)0.1072 (3)0.0358 (10)
H120.94120.59290.04620.043*
C130.9756 (4)0.6894 (3)0.1196 (3)0.0349 (9)
H130.95800.74770.06780.042*
C141.0117 (4)0.6963 (3)0.2085 (3)0.0377 (10)
H141.02000.75970.21760.045*
C151.0359 (4)0.6109 (3)0.2849 (3)0.0340 (9)
H151.05910.61650.34600.041*
C160.7608 (4)0.7089 (3)0.8479 (2)0.0265 (8)
C170.6479 (4)0.7507 (3)0.7931 (3)0.0305 (9)
H170.56140.72950.81470.037*
C180.6632 (4)0.8231 (3)0.7073 (3)0.0306 (9)
H180.58590.85140.67020.037*
C190.7888 (4)0.8564 (3)0.6729 (3)0.0277 (8)
C200.8995 (4)0.8146 (3)0.7303 (3)0.0284 (8)
H200.98610.83580.70920.034*
C210.8855 (4)0.7429 (3)0.8170 (3)0.0291 (9)
H210.96170.71670.85580.035*
C220.8072 (4)0.9304 (3)0.5808 (3)0.0279 (8)
H220.89750.94370.55940.033*
C230.7081 (4)0.9805 (3)0.5246 (3)0.0330 (9)
H230.61700.96830.54410.040*
C240.6366 (4)0.5879 (3)0.9591 (3)0.0381 (10)
H24A0.60560.57100.90240.046*
H24B0.56340.63450.98190.046*
C250.6680 (3)0.4951 (3)1.0395 (3)0.0287 (9)
C260.7175 (4)0.4054 (3)1.0175 (3)0.0364 (10)
H260.73090.40240.95140.044*
C270.7477 (4)0.3194 (3)1.0922 (3)0.0418 (10)
H270.78230.25811.07660.050*
C280.7279 (4)0.3225 (3)1.1887 (3)0.0402 (10)
H280.74680.26351.23950.048*
C290.6802 (4)0.4122 (3)1.2100 (3)0.0392 (10)
H290.66830.41551.27610.047*
C300.6495 (4)0.4976 (3)1.1359 (3)0.0339 (9)
H300.61510.55881.15180.041*
C310.5003 (4)0.2542 (3)0.8087 (2)0.0272 (8)
C320.3980 (4)0.2181 (3)0.8771 (3)0.0306 (9)
H320.30550.23350.86080.037*
C330.4313 (4)0.1599 (3)0.9687 (3)0.0312 (9)
H330.36110.13551.01500.037*
C340.5662 (4)0.1366 (3)0.9941 (3)0.0293 (8)
C350.6680 (4)0.1754 (3)0.9255 (3)0.0326 (9)
H350.76040.16130.94210.039*
C360.6354 (4)0.2333 (3)0.8347 (3)0.0330 (9)
H360.70530.25950.78920.040*
C370.6052 (4)0.0718 (3)1.0889 (3)0.0319 (9)
H370.69910.06051.10130.038*
C380.5207 (4)0.0273 (3)1.1591 (3)0.0317 (9)
H380.42590.03751.14940.038*
C390.3446 (4)0.3208 (3)0.6810 (3)0.0317 (9)
H39A0.27960.36510.71300.038*
H39B0.31130.25520.69510.038*
C400.3582 (3)0.3660 (3)0.5727 (3)0.0298 (9)
C410.4149 (4)0.3069 (3)0.5108 (3)0.0341 (9)
H410.44140.23740.53650.041*
C420.4326 (4)0.3493 (3)0.4114 (3)0.0365 (10)
H420.47050.30860.36910.044*
C430.3955 (4)0.4507 (3)0.3735 (3)0.0375 (10)
H430.40900.47970.30550.045*
C440.3390 (4)0.5096 (3)0.4347 (3)0.0354 (9)
H440.31320.57910.40890.043*
C450.3199 (4)0.4670 (3)0.5338 (3)0.0319 (9)
H450.28010.50760.57570.038*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0257 (13)0.0339 (16)0.0294 (14)−0.0089 (11)−0.0034 (11)0.0002 (12)
O20.0388 (17)0.0464 (19)0.0431 (17)−0.0049 (14)−0.0069 (14)0.0104 (14)
O30.0341 (16)0.0445 (18)0.0417 (17)−0.0109 (13)0.0066 (13)0.0016 (14)
O40.0312 (14)0.0374 (16)0.0290 (14)−0.0146 (12)−0.0044 (11)0.0044 (12)
O50.0268 (14)0.0438 (18)0.0378 (16)−0.0080 (12)0.0017 (12)0.0005 (13)
O60.0315 (16)0.0483 (19)0.0454 (17)0.0029 (14)−0.0119 (13)0.0071 (14)
O70.0235 (13)0.0436 (17)0.0276 (14)−0.0091 (12)−0.0047 (10)0.0006 (12)
O80.0308 (16)0.059 (2)0.0412 (17)−0.0091 (14)−0.0093 (13)0.0045 (15)
O90.0378 (16)0.0431 (18)0.0361 (16)−0.0109 (13)0.0046 (13)0.0017 (13)
N10.0334 (19)0.0282 (19)0.0377 (19)−0.0061 (15)0.0011 (15)−0.0028 (15)
N20.0301 (18)0.034 (2)0.0288 (17)−0.0060 (15)−0.0038 (14)−0.0022 (15)
N30.038 (2)0.0303 (19)0.0262 (17)−0.0060 (15)−0.0031 (14)−0.0018 (14)
C10.030 (2)0.027 (2)0.0239 (19)−0.0026 (16)−0.0026 (15)−0.0059 (16)
C20.0233 (18)0.031 (2)0.029 (2)−0.0083 (16)0.0009 (15)−0.0090 (17)
C30.0261 (19)0.029 (2)0.028 (2)−0.0006 (16)−0.0049 (15)−0.0036 (17)
C40.029 (2)0.026 (2)0.0272 (19)−0.0054 (16)−0.0015 (15)−0.0071 (16)
C50.0248 (19)0.032 (2)0.036 (2)−0.0105 (17)0.0019 (16)−0.0062 (18)
C60.0233 (19)0.034 (2)0.030 (2)−0.0074 (16)−0.0011 (15)−0.0058 (17)
C70.0268 (19)0.028 (2)0.030 (2)−0.0069 (16)0.0003 (16)−0.0076 (17)
C80.032 (2)0.028 (2)0.032 (2)−0.0109 (17)0.0018 (17)0.0002 (17)
C90.0268 (19)0.033 (2)0.028 (2)−0.0094 (17)−0.0036 (15)0.0000 (17)
C100.0179 (17)0.032 (2)0.033 (2)−0.0075 (15)−0.0007 (15)−0.0066 (17)
C110.032 (2)0.030 (2)0.036 (2)−0.0085 (17)−0.0025 (17)−0.0089 (18)
C120.033 (2)0.046 (3)0.027 (2)−0.0087 (19)−0.0079 (16)−0.0023 (19)
C130.027 (2)0.037 (3)0.035 (2)−0.0066 (18)0.0005 (16)0.0012 (19)
C140.037 (2)0.026 (2)0.048 (3)−0.0057 (18)−0.0028 (19)−0.0046 (19)
C150.034 (2)0.038 (3)0.032 (2)−0.0079 (18)−0.0061 (17)−0.0081 (18)
C160.0287 (19)0.027 (2)0.0235 (19)−0.0093 (16)−0.0039 (15)−0.0026 (16)
C170.027 (2)0.034 (2)0.031 (2)−0.0112 (17)−0.0017 (16)−0.0056 (18)
C180.0242 (19)0.035 (2)0.031 (2)−0.0030 (17)−0.0064 (15)−0.0043 (18)
C190.030 (2)0.024 (2)0.028 (2)−0.0050 (16)−0.0020 (16)−0.0051 (16)
C200.0242 (19)0.029 (2)0.031 (2)−0.0067 (16)−0.0023 (15)−0.0031 (17)
C210.0259 (19)0.032 (2)0.029 (2)−0.0050 (16)−0.0050 (15)−0.0049 (17)
C220.0256 (19)0.030 (2)0.028 (2)−0.0066 (16)0.0027 (15)−0.0071 (17)
C230.030 (2)0.037 (2)0.030 (2)−0.0100 (18)0.0024 (16)−0.0046 (18)
C240.032 (2)0.044 (3)0.036 (2)−0.0197 (19)−0.0011 (17)0.0021 (19)
C250.0201 (18)0.034 (2)0.031 (2)−0.0105 (16)−0.0023 (15)−0.0025 (17)
C260.028 (2)0.047 (3)0.034 (2)−0.0096 (19)0.0008 (17)−0.010 (2)
C270.036 (2)0.036 (3)0.056 (3)−0.0060 (19)−0.003 (2)−0.015 (2)
C280.031 (2)0.038 (3)0.043 (2)−0.0072 (19)−0.0041 (18)0.006 (2)
C290.035 (2)0.050 (3)0.031 (2)−0.014 (2)0.0031 (17)−0.006 (2)
C300.031 (2)0.035 (2)0.037 (2)−0.0067 (17)−0.0020 (17)−0.0096 (19)
C310.032 (2)0.025 (2)0.0238 (19)−0.0052 (16)−0.0023 (15)−0.0042 (16)
C320.0274 (19)0.031 (2)0.031 (2)−0.0023 (16)−0.0003 (16)−0.0062 (17)
C330.031 (2)0.036 (2)0.026 (2)−0.0092 (17)0.0047 (16)−0.0075 (18)
C340.033 (2)0.026 (2)0.028 (2)−0.0063 (17)−0.0012 (16)−0.0052 (16)
C350.026 (2)0.041 (2)0.032 (2)−0.0053 (17)−0.0038 (16)−0.0104 (18)
C360.029 (2)0.042 (2)0.026 (2)−0.0076 (18)0.0017 (16)−0.0042 (18)
C370.030 (2)0.032 (2)0.034 (2)−0.0033 (17)0.0007 (17)−0.0116 (18)
C380.030 (2)0.034 (2)0.029 (2)−0.0006 (17)−0.0053 (16)−0.0069 (18)
C390.0252 (19)0.038 (2)0.029 (2)−0.0053 (17)−0.0062 (15)−0.0024 (18)
C400.0206 (18)0.036 (2)0.032 (2)−0.0080 (16)−0.0051 (15)−0.0042 (18)
C410.028 (2)0.034 (2)0.040 (2)−0.0067 (17)−0.0052 (17)−0.0063 (19)
C420.028 (2)0.045 (3)0.040 (2)−0.0072 (19)−0.0011 (17)−0.016 (2)
C430.030 (2)0.050 (3)0.029 (2)−0.0078 (19)−0.0063 (17)−0.003 (2)
C440.028 (2)0.038 (2)0.035 (2)−0.0027 (18)−0.0040 (17)0.0009 (19)
C450.0229 (19)0.037 (2)0.035 (2)−0.0022 (17)−0.0033 (16)−0.0074 (18)

Geometric parameters (Å, °)

O1—C11.362 (4)C19—C221.454 (5)
O1—C91.445 (4)C20—C211.379 (5)
O2—N11.239 (4)C20—H200.9500
O3—N11.228 (4)C21—H210.9500
O4—C161.364 (4)C22—C231.321 (5)
O4—C241.441 (4)C22—H220.9500
O5—N21.224 (4)C23—H230.9500
O6—N21.239 (4)C24—C251.500 (5)
O7—C311.359 (4)C24—H24A0.9900
O7—C391.451 (4)C24—H24B0.9900
O8—N31.231 (4)C25—C301.376 (5)
O9—N31.237 (4)C25—C261.383 (5)
N1—C81.449 (5)C26—C271.393 (6)
N2—C231.435 (5)C26—H260.9500
N3—C381.435 (5)C27—C281.380 (6)
C1—C61.391 (5)C27—H270.9500
C1—C21.396 (5)C28—C291.376 (6)
C2—C31.385 (5)C28—H280.9500
C2—H20.9500C29—C301.385 (6)
C3—C41.399 (5)C29—H290.9500
C3—H30.9500C30—H300.9500
C4—C51.392 (5)C31—C321.393 (5)
C4—C71.458 (5)C31—C361.397 (5)
C5—C61.381 (5)C32—C331.383 (5)
C5—H50.9500C32—H320.9500
C6—H60.9500C33—C341.392 (5)
C7—C81.324 (5)C33—H330.9500
C7—H70.9500C34—C351.402 (5)
C8—H80.9500C34—C371.462 (5)
C9—C101.504 (5)C35—C361.369 (5)
C9—H9A0.9900C35—H350.9500
C9—H9B0.9900C36—H360.9500
C10—C151.379 (5)C37—C381.325 (5)
C10—C111.393 (5)C37—H370.9500
C11—C121.388 (5)C38—H380.9500
C11—H110.9500C39—C401.504 (5)
C12—C131.362 (6)C39—H39A0.9900
C12—H120.9500C39—H39B0.9900
C13—C141.383 (5)C40—C451.384 (5)
C13—H130.9500C40—C411.389 (5)
C14—C151.393 (5)C41—C421.386 (5)
C14—H140.9500C41—H410.9500
C15—H150.9500C42—C431.385 (6)
C16—C211.388 (5)C42—H420.9500
C16—C171.392 (5)C43—C441.378 (6)
C17—C181.377 (5)C43—H430.9500
C17—H170.9500C44—C451.385 (5)
C18—C191.400 (5)C44—H440.9500
C18—H180.9500C45—H450.9500
C19—C201.395 (5)
C1—O1—C9117.4 (3)C23—C22—C19125.1 (3)
C16—O4—C24117.4 (3)C23—C22—H22117.4
C31—O7—C39117.7 (3)C19—C22—H22117.4
O3—N1—O2123.5 (3)C22—C23—N2121.6 (3)
O3—N1—C8120.0 (3)C22—C23—H23119.2
O2—N1—C8116.5 (3)N2—C23—H23119.2
O5—N2—O6122.7 (3)O4—C24—C25107.8 (3)
O5—N2—C23120.3 (3)O4—C24—H24A110.1
O6—N2—C23117.0 (3)C25—C24—H24A110.1
O8—N3—O9122.5 (3)O4—C24—H24B110.1
O8—N3—C38121.0 (3)C25—C24—H24B110.1
O9—N3—C38116.4 (3)H24A—C24—H24B108.5
O1—C1—C6116.0 (3)C30—C25—C26118.9 (4)
O1—C1—C2124.3 (3)C30—C25—C24121.0 (4)
C6—C1—C2119.6 (3)C26—C25—C24120.2 (4)
C3—C2—C1119.6 (3)C25—C26—C27120.2 (4)
C3—C2—H2120.2C25—C26—H26119.9
C1—C2—H2120.2C27—C26—H26119.9
C2—C3—C4121.1 (3)C28—C27—C26120.6 (4)
C2—C3—H3119.4C28—C27—H27119.7
C4—C3—H3119.4C26—C27—H27119.7
C5—C4—C3118.3 (3)C29—C28—C27119.0 (4)
C5—C4—C7118.9 (3)C29—C28—H28120.5
C3—C4—C7122.8 (3)C27—C28—H28120.5
C6—C5—C4121.1 (3)C28—C29—C30120.5 (4)
C6—C5—H5119.5C28—C29—H29119.8
C4—C5—H5119.5C30—C29—H29119.8
C5—C6—C1120.2 (3)C25—C30—C29120.9 (4)
C5—C6—H6119.9C25—C30—H30119.5
C1—C6—H6119.9C29—C30—H30119.5
C8—C7—C4126.1 (3)O7—C31—C32124.9 (3)
C8—C7—H7116.9O7—C31—C36115.8 (3)
C4—C7—H7116.9C32—C31—C36119.3 (3)
C7—C8—N1120.8 (3)C33—C32—C31120.0 (3)
C7—C8—H8119.6C33—C32—H32120.0
N1—C8—H8119.6C31—C32—H32120.0
O1—C9—C10108.1 (3)C32—C33—C34120.9 (3)
O1—C9—H9A110.1C32—C33—H33119.5
C10—C9—H9A110.1C34—C33—H33119.5
O1—C9—H9B110.1C33—C34—C35118.6 (3)
C10—C9—H9B110.1C33—C34—C37122.2 (3)
H9A—C9—H9B108.4C35—C34—C37119.2 (3)
C15—C10—C11118.6 (3)C36—C35—C34120.7 (4)
C15—C10—C9121.0 (3)C36—C35—H35119.7
C11—C10—C9120.4 (3)C34—C35—H35119.7
C12—C11—C10120.3 (4)C35—C36—C31120.5 (3)
C12—C11—H11119.9C35—C36—H36119.7
C10—C11—H11119.9C31—C36—H36119.7
C13—C12—C11121.1 (4)C38—C37—C34125.7 (4)
C13—C12—H12119.5C38—C37—H37117.2
C11—C12—H12119.5C34—C37—H37117.2
C12—C13—C14119.2 (4)C37—C38—N3121.3 (4)
C12—C13—H13120.4C37—C38—H38119.3
C14—C13—H13120.4N3—C38—H38119.3
C13—C14—C15120.4 (4)O7—C39—C40106.1 (3)
C13—C14—H14119.8O7—C39—H39A110.5
C15—C14—H14119.8C40—C39—H39A110.5
C10—C15—C14120.5 (4)O7—C39—H39B110.5
C10—C15—H15119.8C40—C39—H39B110.5
C14—C15—H15119.8H39A—C39—H39B108.7
O4—C16—C21115.9 (3)C45—C40—C41119.2 (3)
O4—C16—C17124.4 (3)C45—C40—C39120.8 (3)
C21—C16—C17119.7 (3)C41—C40—C39120.0 (4)
C18—C17—C16119.2 (3)C42—C41—C40120.0 (4)
C18—C17—H17120.4C42—C41—H41120.0
C16—C17—H17120.4C40—C41—H41120.0
C17—C18—C19122.2 (3)C43—C42—C41120.3 (4)
C17—C18—H18118.9C43—C42—H42119.9
C19—C18—H18118.9C41—C42—H42119.9
C20—C19—C18117.3 (3)C44—C43—C42119.9 (4)
C20—C19—C22120.0 (3)C44—C43—H43120.0
C18—C19—C22122.7 (3)C42—C43—H43120.0
C21—C20—C19121.2 (3)C43—C44—C45119.8 (4)
C21—C20—H20119.4C43—C44—H44120.1
C19—C20—H20119.4C45—C44—H44120.1
C20—C21—C16120.3 (3)C40—C45—C44120.8 (4)
C20—C21—H21119.8C40—C45—H45119.6
C16—C21—H21119.8C44—C45—H45119.6
C9—O1—C1—C6169.3 (3)C19—C22—C23—N2179.5 (3)
C9—O1—C1—C2−9.1 (5)O5—N2—C23—C229.6 (6)
O1—C1—C2—C3177.1 (3)O6—N2—C23—C22−169.3 (4)
C6—C1—C2—C3−1.3 (5)C16—O4—C24—C25168.5 (3)
C1—C2—C3—C4−0.7 (6)O4—C24—C25—C3091.2 (4)
C2—C3—C4—C51.6 (6)O4—C24—C25—C26−88.2 (4)
C2—C3—C4—C7−176.3 (3)C30—C25—C26—C270.0 (5)
C3—C4—C5—C6−0.6 (6)C24—C25—C26—C27179.4 (3)
C7—C4—C5—C6177.4 (3)C25—C26—C27—C280.5 (6)
C4—C5—C6—C1−1.3 (6)C26—C27—C28—C29−1.3 (6)
O1—C1—C6—C5−176.2 (3)C27—C28—C29—C301.6 (6)
C2—C1—C6—C52.3 (6)C26—C25—C30—C290.3 (5)
C5—C4—C7—C8−178.6 (4)C24—C25—C30—C29−179.1 (3)
C3—C4—C7—C8−0.6 (6)C28—C29—C30—C25−1.1 (6)
C4—C7—C8—N1177.6 (3)C39—O7—C31—C32−8.1 (5)
O3—N1—C8—C7−6.0 (6)C39—O7—C31—C36171.5 (3)
O2—N1—C8—C7175.5 (4)O7—C31—C32—C33177.7 (4)
C1—O1—C9—C10−170.1 (3)C36—C31—C32—C33−1.8 (6)
O1—C9—C10—C15118.0 (4)C31—C32—C33—C340.1 (6)
O1—C9—C10—C11−63.0 (4)C32—C33—C34—C351.5 (6)
C15—C10—C11—C120.0 (5)C32—C33—C34—C37−177.4 (4)
C9—C10—C11—C12−179.0 (3)C33—C34—C35—C36−1.2 (6)
C10—C11—C12—C130.2 (6)C37—C34—C35—C36177.6 (4)
C11—C12—C13—C140.2 (6)C34—C35—C36—C31−0.5 (6)
C12—C13—C14—C15−0.8 (6)O7—C31—C36—C35−177.5 (3)
C11—C10—C15—C14−0.7 (5)C32—C31—C36—C352.0 (6)
C9—C10—C15—C14178.3 (3)C33—C34—C37—C381.3 (6)
C13—C14—C15—C101.0 (6)C35—C34—C37—C38−177.5 (4)
C24—O4—C16—C21−172.4 (3)C34—C37—C38—N3179.3 (3)
C24—O4—C16—C176.4 (5)O8—N3—C38—C37−2.5 (6)
O4—C16—C17—C18−176.7 (3)O9—N3—C38—C37177.4 (4)
C21—C16—C17—C182.1 (6)C31—O7—C39—C40−169.0 (3)
C16—C17—C18—C190.0 (6)O7—C39—C40—C45−100.5 (4)
C17—C18—C19—C20−1.1 (6)O7—C39—C40—C4176.8 (4)
C17—C18—C19—C22177.9 (4)C45—C40—C41—C420.1 (5)
C18—C19—C20—C210.3 (6)C39—C40—C41—C42−177.3 (3)
C22—C19—C20—C21−178.7 (3)C40—C41—C42—C430.7 (5)
C19—C20—C21—C161.7 (6)C41—C42—C43—C44−0.8 (6)
O4—C16—C21—C20176.0 (3)C42—C43—C44—C450.2 (6)
C17—C16—C21—C20−2.9 (6)C41—C40—C45—C44−0.8 (5)
C20—C19—C22—C23−174.4 (4)C39—C40—C45—C44176.6 (3)
C18—C19—C22—C236.6 (6)C43—C44—C45—C400.6 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···O8i0.952.563.503 (5)175
C8—H8···O8i0.952.383.322 (5)175
C5—H5···O9ii0.952.583.493 (4)162
C12—H12···O4iii0.952.463.284 (5)145
C20—H20···O5iv0.952.493.373 (4)155
C22—H22···O5iv0.952.593.448 (4)150
C18—H18···O6v0.952.403.326 (4)166
C33—H33···O3ii0.952.403.325 (4)163
C45—H45···O1vi0.952.583.413 (5)147

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y, −z+2; (iii) x, y, z−1; (iv) −x+2, −y+2, −z+1; (v) −x+1, −y+2, −z+1; (vi) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2304).

References

  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Gao, F., Xie, T., Cheng, Z., Hu, N., Yang, L., Gong, Y., Zhang, S. & Li, H. (2008). J. Fluoresc 18, 787–799. [PubMed]
  • Gerkin, R. E. (1999). Acta Cryst. C55, 2140–2142. [PubMed]
  • Hooft, R. (1998). COLLECT Nonius BV, Delft, The Netherlands.
  • Hunter, R., Younis, Y., Muhanji, C. I., Curtin, T.-L., Naidoo, K. J., Petersen, M., Bailey, C. M., Basavapathruni, A. & Anderson, K. S. (2008). Bioorg. Med. Chem.16, 10270–10280. [PMC free article] [PubMed]
  • Jones, L. H., Dupont, T., Mowbray, C. E. & Newman, S. D. (2006). Org. Lett.8, 1725–1727. [PubMed]
  • Kennedy, A. R., Kipkorir, Z. R., Muhanji, C. I. & Okoth, M. O. (2010). Acta Cryst. E66, o2110. [PMC free article] [PubMed]
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp 307–326. New York: Academic Press.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stomberg, R. & Lundquist, K. (1994). Z. Kristallogr.209, 835–836.
  • UNAIDS/WHO (2009). Report on the global AIDS epidemic, 17th April 2009. http://www.unaids.org 2008.
  • Wang, D.-J., Fan, L. & Zheng, J. (2007). Acta Cryst. E63, o2979.
  • Younis, Y., Hunter, R., Muhanji, C. I., Hale, I., Singh, R., Bailey, C. M., Sullivan, T. J. & Anderson, K. S. (2010). Bioorg. Med. Chem.18, 4661–4673. [PMC free article] [PubMed]
  • Zheng, C.-Y., Wang, D.-J. & Fan, L. (2008). Acta Cryst. E64, o2326. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography