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The title compound, 1-(5,8-di­hydro-1,4-di­hydroxy-5,8-dioxo-2-naphthyl)-4-methyl­pent-3-en-1-yl cinnamate, C25H22O6, crystallizes in space group P21. The phenyl ring of the cinnamate is anti to the carbonyl group of the same moiety [C—C—C—C = −175.6 (2)°] and is nearly parallel to the naphthyl ring system. Two six-membered rings formed by intramolecular hydrogen bonds, with O—H...O distances of 2.587 (2) and 2.589 (2) Å, occur on either side of the fused ring system, creating a tetracyclic pyrene-shaped system. The phenyl ring forms an intermolecular stack with the benzo­quinone ring, as a result of aromatic π–π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101011842/de1171sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101011842/de1171Isup2.hkl
Contains datablock I

CCDC reference: 174838

Comment top

Arnebin-1 (β,β-dimethyl acryloyl shikonin), a naturally occurring naphthoquinone from the root of the plant Arnebia nobilis, belongs to the alkanin/shikonin family (Shukla et al., 1969). The toxic effects of this compound restricted its further development as a clinically useful therapeutic agent, in spite of its wound healing, antiinflammatory, antithrombotic, antimicrobial and anticancer activities (Papageorgiou et al., 1999). This necessitated the development of numerous analogues of shikonin with greatly reduced toxicity. One such analogue is the title compound, (I), which shows a growth-inhibiting effect on prostate cancer cells (Gaddipati et al., 2000). This prompted us to undertake the present diffraction study in order to confirm the overall three-dimensional structure of (I). \sch

The conformation of (I) and the atom-numbering scheme are shown in Fig. 1. The molecule contains one naphthaquinone ring (fused ring system A/B), to which a phenyl ring (C) is attached via an ester bond, and one chiral centre (C11). Although the present study does not establish the absolute configuration of the molecule [Flack (1983) parameter 0.3 (9)], the parent shikonin has the R configuration, as determined by the chemical degradation method (Arakawa & Nakazaki, 1961). The phenyl ring C is almost parallel with the A/B ring: the interplanar angle between the two rings is 1.7 (1)°. Moreover, the phenyl ring at C19 is anti to the carbonyl group at C17 [C17—C18—C19—C20 - 175.6 (2)°].

The molecule of (I) contains two potential hydrogen-bond donors (–OH groups O5—H5 and O8—H8), which are involved in intramolecular hydrogen-bonding interactions with carbonyl groups C4O4 and C1O1 (Table 2) through the formation of six-membered rings (Fig. 1). The formation of such rings is preferred over intermolecular hydrogen bonding (Bilton et al. 2000). The strong intramolecular O···O distances observed in (I) are in the same range as those found in the parent naphthazarin C at 60 K (Herbstein et al. 1985).

The hydroxyl H atoms, H5 and H8, were located in a difference Fourier map, in view of the ambiguity about their positions in related naphthazarin systems (Herbstein et al. 1985). A comparison of bond lengths in (I) with those of naphthazarin C (neutron diffraction at 60 K) and other related systems (Herbstein et al., 1985, and references therein) shows that, on average, CO is ca 0.05 Å longer (in which molecule?), while C—OH is ca 0.03 Å shorter (in which molecule?). This suggests that, in close analogy with the crystal structure of naphthazarin C, the hydroxyl H atoms are not completely localized in (I) at 100 K and that ordering will be favoured at lower temperatures, since a complete localization is only possible at 0 K.

In addition, weak hydrogen-bonding interactions of the type C—H···O are also observed (Table 2). The crystal packing (Fig. 2) further shows that the phenyl ring C stacks with the benzoquinone ring A, due to aromatic π-π interactions. The average intermolecular stacking distance and the angle between the rings, which overlap substantially in a `face-to-face' orientation as per the model proposed by Hunter (1990), are 3.3 Å and 1.1 (1)°, respectively. The benzoquinone ring being electron deficient, it can allow for a substantial face-to-face overlap with the relatively neutral phenyl ring without much π-π repulsion.

Experimental top

The synthesis of (I) was carried out by hydrolysing β,β-dimethyl acryloyl shikonin with sodium hydroxide, followed by esterification with cinnamic anhydride or cinnamoyl chloride or cinnamic acid and DCC. Which procedure was used here? Define DCC. Crystals of (I) of diffraction quality were grown from hexane-methylene chloride solution (is a mixed solvent correct?) at room temperature.

Refinement top

The hydroxyl H atoms H5 and H8 were located from the difference Fourier map and refined freely. The remaining H atoms were placed in geometrically idealized positions and allowed to ride on their parent atoms, with C—H = 093–0.98 Å and Uiso(H) = 1.2Ueq(C). Query. Three reflections [most disagreeable, Δ(F2)/σ > 6.4] were suppressed during the last cycles of refinement.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: NRCVAX (Gabe et al., 1989), ORTEP (Johnson, 1965) and PLUTO (Motherwell & Clegg, 1978); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with the atom-numbering scheme, showing displacement ellipsoids at the 50% probability level. H atoms are drawn as small spheres of arbitrary radii and intramolecular O—H···O bonds are shown by dotted lines.
[Figure 2] Fig. 2. The packing in (I), showing the intermolecular stacking of rings C and A due to aromatic π-π interaction.
1-(5,8-dihydro-1,4-dihydroxy-5,8-dioxo-2-naphthyl)-4-methylpent-3-en-1-yl cinnamate top
Crystal data top
C25H22O6Dx = 1.361 Mg m3
Mr = 418.43Melting point = 93–94 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 6.1677 (1) ÅCell parameters from 510 reflections
b = 15.7416 (3) Åθ = 4.1–27.4°
c = 10.5141 (2) ŵ = 0.10 mm1
β = 90.763 (1)°T = 100 K
V = 1020.72 (3) Å3Block, red
Z = 20.5 × 0.1 × 0.1 mm
F(000) = 440
Data collection top
Bruker SMART CCD area-detector
diffractometer
4357 independent reflections
Radiation source: fine-focus sealed tube4011 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω scanθmax = 27.5°, θmin = 1.9°
Absorption correction: ψ-scan
(XPREP; Sheldrick, 1994)
h = 87
Tmin = 0.885, Tmax = 1.000k = 2020
7463 measured reflectionsl = 1311
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0219P)2 + 0.7688P]
where P = (Fo2 + 2Fc2)/3
4357 reflections(Δ/σ)max = 0.002
290 parametersΔρmax = 0.25 e Å3
1 restraintΔρmin = 0.25 e Å3
Crystal data top
C25H22O6V = 1020.72 (3) Å3
Mr = 418.43Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.1677 (1) ŵ = 0.10 mm1
b = 15.7416 (3) ÅT = 100 K
c = 10.5141 (2) Å0.5 × 0.1 × 0.1 mm
β = 90.763 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4357 independent reflections
Absorption correction: ψ-scan
(XPREP; Sheldrick, 1994)
4011 reflections with I > 2σ(I)
Tmin = 0.885, Tmax = 1.000Rint = 0.028
7463 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0411 restraint
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.25 e Å3
4357 reflectionsΔρmin = 0.25 e Å3
290 parameters
Special details top

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) top
xyzUiso*/Ueq
C10.6313 (4)0.08045 (14)0.4190 (2)0.0173 (4)
O10.4586 (3)0.04035 (11)0.40111 (15)0.0225 (4)
C20.7810 (4)0.09387 (14)0.3125 (2)0.0198 (5)
H20.74360.07290.23240.024*
C30.9693 (4)0.13538 (14)0.3278 (2)0.0200 (5)
H31.06060.14110.25860.024*
C41.0356 (3)0.17213 (14)0.4512 (2)0.0165 (4)
O41.2094 (3)0.21283 (10)0.46141 (15)0.0207 (3)
C50.9503 (3)0.19095 (13)0.67999 (19)0.0146 (4)
O51.1341 (3)0.23606 (10)0.70031 (15)0.0184 (3)
H51.201 (5)0.240 (2)0.629 (3)0.038 (9)*
C60.8138 (3)0.17673 (14)0.78492 (19)0.0147 (4)
H60.85460.19740.86450.018*
C70.6217 (3)0.13288 (13)0.7716 (2)0.0148 (4)
C80.5603 (3)0.10094 (13)0.6490 (2)0.0141 (4)
O80.3717 (3)0.05787 (10)0.63994 (16)0.0190 (3)
H80.366 (5)0.038 (2)0.562 (3)0.050 (10)*
C90.6946 (3)0.11375 (13)0.5441 (2)0.0148 (4)
C100.8928 (4)0.15915 (13)0.5599 (2)0.0139 (4)
C110.4692 (3)0.11656 (13)0.88009 (19)0.0145 (4)
H110.32150.13160.85320.017*
O110.5373 (2)0.17241 (10)0.98345 (14)0.0166 (3)
C120.4713 (4)0.02440 (14)0.9277 (2)0.0183 (4)
H12A0.36790.01910.99600.022*
H12B0.42300.01240.85900.022*
C130.6898 (4)0.00625 (15)0.9753 (2)0.0183 (4)
H130.81100.01700.93670.022*
C140.7272 (4)0.06321 (14)1.0671 (2)0.0176 (4)
C150.9552 (4)0.08868 (17)1.1043 (2)0.0264 (5)
H15A0.97380.14851.09020.040*
H15B0.98020.07611.19260.040*
H15C1.05660.05761.05370.040*
C160.5514 (4)0.10676 (16)1.1415 (2)0.0243 (5)
H16A0.54060.08081.22380.036*
H16B0.58650.16581.15140.036*
H16C0.41550.10131.09670.036*
C170.3800 (3)0.20142 (15)1.06159 (19)0.0182 (4)
O170.1894 (3)0.18486 (13)1.04712 (15)0.0268 (4)
C180.4685 (4)0.25339 (15)1.1664 (2)0.0191 (4)
H180.37710.26681.23310.023*
C190.6715 (4)0.28248 (14)1.1718 (2)0.0176 (4)
H190.75710.27181.10140.021*
C200.7746 (4)0.32971 (14)1.2774 (2)0.0172 (4)
C210.6812 (4)0.33297 (14)1.3995 (2)0.0191 (4)
H210.54730.30781.41370.023*
C220.7910 (4)0.37412 (15)1.4982 (2)0.0224 (5)
H220.73040.37591.57860.027*
C230.9904 (4)0.41266 (15)1.4776 (2)0.0252 (5)
H231.06250.43981.54440.030*
C241.0823 (4)0.41081 (15)1.3576 (2)0.0248 (5)
H241.21460.43731.34370.030*
C250.9745 (4)0.36890 (15)1.2580 (2)0.0208 (5)
H251.03670.36711.17800.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0221 (11)0.0135 (10)0.0164 (10)0.0031 (9)0.0016 (8)0.0008 (8)
O10.0240 (9)0.0254 (9)0.0180 (8)0.0034 (7)0.0015 (7)0.0046 (7)
C20.0292 (12)0.0180 (11)0.0120 (10)0.0035 (9)0.0006 (9)0.0001 (8)
C30.0257 (12)0.0206 (11)0.0139 (10)0.0044 (9)0.0057 (9)0.0014 (9)
C40.0194 (11)0.0142 (10)0.0160 (10)0.0031 (9)0.0019 (8)0.0031 (8)
O40.0202 (8)0.0217 (8)0.0202 (8)0.0016 (7)0.0039 (6)0.0024 (6)
C50.0150 (10)0.0114 (10)0.0174 (10)0.0004 (8)0.0006 (8)0.0009 (8)
O50.0167 (8)0.0219 (8)0.0166 (7)0.0052 (6)0.0027 (6)0.0011 (6)
C60.0171 (10)0.0146 (10)0.0122 (9)0.0008 (8)0.0002 (8)0.0021 (8)
C70.0146 (10)0.0144 (10)0.0153 (10)0.0019 (8)0.0002 (8)0.0024 (8)
C80.0143 (10)0.0132 (10)0.0149 (10)0.0016 (8)0.0012 (8)0.0009 (8)
O80.0172 (8)0.0222 (8)0.0176 (8)0.0035 (6)0.0011 (6)0.0033 (6)
C90.0161 (10)0.0123 (9)0.0161 (10)0.0022 (8)0.0006 (8)0.0012 (8)
C100.0173 (10)0.0137 (9)0.0108 (9)0.0011 (8)0.0023 (8)0.0013 (7)
C110.0137 (10)0.0184 (10)0.0115 (9)0.0004 (8)0.0012 (8)0.0002 (8)
O110.0146 (7)0.0217 (8)0.0134 (7)0.0007 (6)0.0023 (6)0.0033 (6)
C120.0180 (11)0.0190 (11)0.0179 (10)0.0033 (9)0.0008 (8)0.0032 (9)
C130.0164 (11)0.0226 (11)0.0161 (10)0.0004 (9)0.0042 (8)0.0012 (9)
C140.0174 (11)0.0180 (11)0.0174 (10)0.0013 (9)0.0025 (8)0.0036 (8)
C150.0182 (11)0.0300 (13)0.0310 (12)0.0011 (10)0.0001 (9)0.0119 (11)
C160.0213 (11)0.0255 (12)0.0262 (12)0.0007 (10)0.0030 (9)0.0089 (10)
C170.0181 (11)0.0239 (12)0.0129 (9)0.0019 (9)0.0032 (8)0.0035 (8)
O170.0160 (8)0.0456 (11)0.0189 (8)0.0014 (8)0.0016 (6)0.0067 (8)
C180.0204 (11)0.0231 (11)0.0140 (10)0.0038 (9)0.0019 (8)0.0010 (8)
C190.0225 (11)0.0185 (10)0.0119 (9)0.0017 (8)0.0036 (8)0.0000 (8)
C200.0209 (11)0.0138 (10)0.0168 (10)0.0028 (9)0.0008 (8)0.0010 (9)
C210.0207 (11)0.0170 (10)0.0194 (11)0.0020 (9)0.0001 (8)0.0007 (9)
C220.0339 (13)0.0180 (11)0.0154 (10)0.0038 (10)0.0021 (9)0.0022 (9)
C230.0326 (13)0.0186 (11)0.0244 (11)0.0005 (10)0.0055 (10)0.0048 (10)
C240.0242 (12)0.0176 (11)0.0326 (12)0.0033 (9)0.0014 (10)0.0010 (10)
C250.0233 (11)0.0199 (11)0.0192 (10)0.0004 (9)0.0024 (9)0.0002 (9)
Geometric parameters (Å, º) top
C1—O11.250 (3)C13—C141.335 (3)
C1—C91.464 (3)C13—H130.9300
C1—C21.476 (3)C14—C161.510 (3)
C2—C31.340 (3)C14—C151.509 (3)
C2—H20.9300C15—H15A0.9600
C3—C41.474 (3)C15—H15B0.9600
C3—H30.9300C15—H15C0.9600
C4—O41.252 (3)C16—H16A0.9600
C4—C101.467 (3)C16—H16B0.9600
C5—O51.352 (3)C16—H16C0.9600
C5—C101.400 (3)C17—O171.212 (3)
C5—C61.414 (3)C17—C181.472 (3)
O5—H50.87 (3)C18—C191.334 (3)
C6—C71.377 (3)C18—H180.9300
C6—H60.9300C19—C201.474 (3)
C7—C81.430 (3)C19—H190.9300
C7—C111.510 (3)C20—C251.396 (3)
C8—O81.349 (3)C20—C211.415 (3)
C8—C91.403 (3)C21—C221.391 (3)
O8—H80.88 (4)C21—H210.9300
C9—C101.424 (3)C22—C231.391 (4)
C11—O111.455 (2)C22—H220.9300
C11—C121.535 (3)C23—C241.390 (4)
C11—H110.9800C23—H230.9300
O11—C171.358 (3)C24—C251.398 (3)
C12—C131.511 (3)C24—H240.9300
C12—H12A0.9700C25—H250.9300
C12—H12B0.9700
O1—C1—C9122.1 (2)C14—C13—C12126.8 (2)
O1—C1—C2119.9 (2)C14—C13—H13116.6
C9—C1—C2118.0 (2)C12—C13—H13116.6
C3—C2—C1121.9 (2)C13—C14—C16124.2 (2)
C3—C2—H2119.1C13—C14—C15121.1 (2)
C1—C2—H2119.1C16—C14—C15114.71 (19)
C2—C3—C4121.8 (2)C14—C15—H15A109.5
C2—C3—H3119.1C14—C15—H15B109.5
C4—C3—H3119.1H15A—C15—H15B109.5
O4—C4—C10121.78 (19)C14—C15—H15C109.5
O4—C4—C3120.26 (19)H15A—C15—H15C109.5
C10—C4—C3117.96 (19)H15B—C15—H15C109.5
O5—C5—C10122.15 (18)C14—C16—H16A109.5
O5—C5—C6117.80 (18)C14—C16—H16B109.5
C10—C5—C6120.05 (18)H16A—C16—H16B109.5
C5—O5—H5108 (2)C14—C16—H16C109.5
C7—C6—C5121.37 (19)H16A—C16—H16C109.5
C7—C6—H6119.3H16B—C16—H16C109.5
C5—C6—H6119.3O17—C17—O11123.4 (2)
C6—C7—C8119.01 (19)O17—C17—C18124.3 (2)
C6—C7—C11123.53 (18)O11—C17—C18112.29 (18)
C8—C7—C11117.46 (18)C19—C18—C17124.1 (2)
O8—C8—C9122.29 (18)C19—C18—H18117.9
O8—C8—C7117.28 (18)C17—C18—H18117.9
C9—C8—C7120.43 (19)C18—C19—C20126.9 (2)
C8—O8—H8106 (2)C18—C19—H19116.5
C8—C9—C10119.70 (18)C20—C19—H19116.5
C8—C9—C1120.14 (19)C25—C20—C21119.2 (2)
C10—C9—C1120.15 (19)C25—C20—C19119.09 (19)
C5—C10—C9119.44 (18)C21—C20—C19121.7 (2)
C5—C10—C4120.37 (19)C22—C21—C20119.6 (2)
C9—C10—C4120.19 (18)C22—C21—H21120.2
O11—C11—C7106.56 (16)C20—C21—H21120.2
O11—C11—C12109.04 (16)C21—C22—C23120.7 (2)
C7—C11—C12113.88 (18)C21—C22—H22119.7
O11—C11—H11109.1C23—C22—H22119.7
C7—C11—H11109.1C22—C23—C24120.2 (2)
C12—C11—H11109.1C22—C23—H23119.9
C17—O11—C11116.98 (16)C24—C23—H23119.9
C13—C12—C11114.42 (18)C23—C24—C25119.6 (2)
C13—C12—H12A108.7C23—C24—H24120.2
C11—C12—H12A108.7C25—C24—H24120.2
C13—C12—H12B108.7C20—C25—C24120.7 (2)
C11—C12—H12B108.7C20—C25—H25119.6
H12A—C12—H12B107.6C24—C25—H25119.6
O1—C1—C2—C3179.0 (2)C3—C4—C10—C91.3 (3)
C9—C1—C2—C30.3 (3)C6—C7—C11—O1114.0 (3)
C1—C2—C3—C41.7 (3)C8—C7—C11—O11165.76 (17)
C2—C3—C4—O4177.8 (2)C6—C7—C11—C12106.3 (2)
C2—C3—C4—C102.4 (3)C8—C7—C11—C1274.0 (2)
O5—C5—C6—C7178.7 (2)C7—C11—O11—C17148.35 (17)
C10—C5—C6—C70.9 (3)C12—C11—O11—C1788.3 (2)
C5—C6—C7—C80.3 (3)O11—C11—C12—C1359.5 (2)
C5—C6—C7—C11179.47 (19)C7—C11—C12—C1359.3 (2)
C6—C7—C8—O8179.60 (19)C11—C12—C13—C14148.8 (2)
C11—C7—C8—O80.7 (3)C12—C13—C14—C160.8 (4)
C6—C7—C8—C90.3 (3)C12—C13—C14—C15179.4 (2)
C11—C7—C8—C9179.92 (19)C11—O11—C17—O171.9 (3)
O8—C8—C9—C10179.47 (19)C11—O11—C17—C18176.89 (18)
C7—C8—C9—C100.2 (3)O17—C17—C18—C19169.2 (2)
O8—C8—C9—C10.4 (3)O11—C17—C18—C1912.0 (3)
C7—C8—C9—C1179.65 (19)C17—C18—C19—C20175.6 (2)
O1—C1—C9—C80.2 (3)C18—C19—C20—C25168.2 (2)
C2—C1—C9—C8178.53 (19)C18—C19—C20—C2114.8 (3)
O1—C1—C9—C10179.9 (2)C25—C20—C21—C220.8 (3)
C2—C1—C9—C101.4 (3)C19—C20—C21—C22176.2 (2)
O5—C5—C10—C9178.60 (19)C20—C21—C22—C230.6 (3)
C6—C5—C10—C91.0 (3)C21—C22—C23—C240.3 (4)
O5—C5—C10—C41.6 (3)C22—C23—C24—C250.9 (4)
C6—C5—C10—C4178.74 (19)C21—C20—C25—C240.1 (3)
C8—C9—C10—C50.4 (3)C19—C20—C25—C24176.9 (2)
C1—C9—C10—C5179.7 (2)C23—C24—C25—C200.7 (4)
C8—C9—C10—C4179.33 (19)C6—C7—C11—C12106.3 (2)
C1—C9—C10—C40.6 (3)C7—C11—C12—C1359.3 (2)
O4—C4—C10—C51.3 (3)C11—C12—C13—C14148.8 (2)
C3—C4—C10—C5178.50 (19)C12—C13—C14—C15179.4 (2)
O4—C4—C10—C9178.93 (19)C12—C13—C14—C160.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O40.87 (3)1.81 (3)2.587 (2)148 (3)
O8—H8···O10.88 (4)1.79 (3)2.589 (2)150 (3)
C3—H3···O17i0.932.473.356 (3)160
C11—H11···O5ii0.982.563.359 (3)138
C16—H16A···O1iii0.962.723.631 (3)159
C21—H21···O4iv0.932.623.538 (3)170
Symmetry codes: (i) x+1, y, z1; (ii) x1, y, z; (iii) x, y, z+1; (iv) x1, y, z+1.

Experimental details

Crystal data
Chemical formulaC25H22O6
Mr418.43
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)6.1677 (1), 15.7416 (3), 10.5141 (2)
β (°) 90.763 (1)
V3)1020.72 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.5 × 0.1 × 0.1
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionψ-scan
(XPREP; Sheldrick, 1994)
Tmin, Tmax0.885, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
7463, 4357, 4011
Rint0.028
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.096, 1.09
No. of reflections4357
No. of parameters290
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.25

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), NRCVAX (Gabe et al., 1989), ORTEP (Johnson, 1965) and PLUTO (Motherwell & Clegg, 1978), SHELXL97.

Selected torsion angles (º) top
C9—C1—C2—C30.3 (3)C3—C4—C10—C91.3 (3)
C1—C2—C3—C41.7 (3)C7—C11—O11—C17148.35 (17)
C2—C3—C4—C102.4 (3)C11—O11—C17—C18176.89 (18)
C10—C5—C6—C70.9 (3)O11—C17—C18—C1912.0 (3)
C5—C6—C7—C80.3 (3)C17—C18—C19—C20175.6 (2)
C6—C7—C8—C90.3 (3)C25—C20—C21—C220.8 (3)
C7—C8—C9—C100.2 (3)C20—C21—C22—C230.6 (3)
C2—C1—C9—C101.4 (3)C21—C22—C23—C240.3 (4)
C6—C5—C10—C91.0 (3)C22—C23—C24—C250.9 (4)
C8—C9—C10—C50.4 (3)C21—C20—C25—C240.1 (3)
C1—C9—C10—C40.6 (3)C23—C24—C25—C200.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O40.87 (3)1.81 (3)2.587 (2)148 (3)
O8—H8···O10.88 (4)1.79 (3)2.589 (2)150 (3)
C3—H3···O17i0.932.4693.356 (3)160
C11—H11···O5ii0.982.5643.359 (3)138
C16—H16A···O1iii0.962.7193.631 (3)159
C21—H21···O4iv0.932.6193.538 (3)170
Symmetry codes: (i) x+1, y, z1; (ii) x1, y, z; (iii) x, y, z+1; (iv) x1, y, z+1.
 

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