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The structure of 4-meth­oxy-1-naphthol, C11H10O2, (I), con­tains an inter­molecular O—H...O hydrogen bond which links the mol­ecules into a simple C(2) chain running parallel to the shortest crystallographic b axis. This chain is reinforced by inter­molecular π–π stacking inter­actions. Comparisons are drawn between the crystal structure of (I) and those of several of its simple analogues, including 1-naphthol and some monosubstituted derivatives, and that of its isomer 7-meth­oxy-2-naphthol. This comparison shows a close similarity in the packing of the mol­ecules of its simple analogues that form π-stacks along the shortest crystallographic axes. A substantial spatial overlap is observed between adjacent mol­ecules in such stacks. In this group of monosubstituted naphthols, the overlap depends mainly on the position of the substituents carried by the naphthalene moiety, and the extent of the overlap depends on the substituent type. By contrast with (I), in the crystal structure of the isomeric 7-meth­oxy-2-naphthol there are no O—H...O hydrogen bonds or π–π stacking inter­actions, and sheets are formed by O—H...π and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109047556/gd3319sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109047556/gd3319Isup2.hkl
Contains datablock I

CCDC reference: 763605

Comment top

This paper is a continuation of our structural studies of 1-naphthol derivatives carrying different substituents at positions 4 or 5. In previous papers, the structures of 4-chloro-1-naphthol [CSD (Allen, 2002) refcode BOTSOT; Rozycka-Sokolowska & Marciniak, 2009a] and 5-amino-1-naphthol (Rozycka-Sokolowska & Marciniak, 2009b) have been reported, and it was found that these compounds and also several of their simple analogues, i.e. 1-naphthol (CSD refcode NAPHOL01; Rozycka-Sokolowska et al., 2004), 1,4- and 1,5-dihydroxynaphthalene [CSD refcodes NPHHQU10 (Gaultier & Hauw, 1967) and VOGRUE (Belskii et al., 1990), respectively], 1,4-dichloro- and 1,5-dibromonaphthalene [CSD refcodes DCLNAQ (Bellows et al., 1978) and DBRNAQ01 (Trotter, 1986), respectively] show π-stacking with substantial spatial overlap in the solid state. Hence they can be regarded as particularly attractive materials for the development of devices with high charge-carrier mobilities (Anthony et al., 2002; Li et al., 1998; Horowitz et al., 1996; Laquindanum et al., 1997; Chen et al., 2006).

Here we report the structure of the title compound, (I) (Fig. 1), as a further example from the group of 4- or 5-substituted 1-naphthols. This work was undertaken to check whether (I), from the viewpoint of the crystal packing, will turn out to be a promising material for applications in electronic device fabrication. We also compare the crystal structure of (I) with those of five of its simple analogues (see scheme), i.e. 1-naphthol, (II), 1,4-dihydroxynaphthalene, (III), 1,5-dihydroxynaphthalene, (IV), 4-chloro-1-naphthol, (V), and 5-amino-1-naphthol, (VI), and also with that of the isomeric 7-methoxy-2-naphthol, (VII) [CSD refcode TEBFIP (Prince et al., 1991)].

The values of bond distances (Table 1) and valence angles within the aromatic rings range from 1.353 (3) to1.424 (3) Å and from 118.6 (2) to 122.7 (2)°, respectively. From among 11 Car—Car bonds, four, i.e. C1—C2, C3—C4, C6—C7 and C8—C9 bonds, are shorter on average by 0.027 Å than the typical aromatic bond length [1.384 (13) Å] given by Allen et al. (1987), and all the other bonds are longer on average by 0.031 Å (Table 1). The C1—O1 bond length is in close agreement with the corresponding distances in the simple analogues of (I), such as (II), (III), (IV), (V) and (VI) [1.376 (1), 1.377, 1.385, 1.394 (3) and 1.379 (4) Å, respectively], and the lengths of C4—O2 and O2—C11 bonds compare well with those found in (VII) and in the methoxy derivatives of naphthalene such as 2-methoxynaphthalene [Car—O = 1.3749 (11) Å and O—Cmethyl = 1.4250 (14) Å; CSD refcode SAYRIT (Bolte & Bauch, 1998)], 1,4-dimethoxynaphthalene [Car—O = 1.37 (1) and 1.39 (1) Å, and O—Cmethyl = 1.46 (1) and 1.44 (1) Å; CSD refcode ALUJIA (Wiedenfeld et al., 1999)] and 1,8-dimethoxynaphthalene [Car—O = 1.359 (2) and 1.362 (2) Å, and O—Cmethyl = 1.425 (2) and 1.419 (2) Å; CSD refcode KEPKUL (Cosmo et al., 1990)] and with the values given by Allen & Kirby (1984). The ten-membered aromatic ring formed by atoms C1—C10 is planar, with the largest out-of-plane deviation of -0.015 (2) Å for atom C9. The deviations of hydroxyl O1 and methoxy O2 and C11 atoms from this plane are only 0.013 (2), -0.015 (2) and -0.117 (3) Å, respectively.

Each molecule of (I) is connected to two others by a strong, nearly linear O—H···O hydrogen bond (Table 2). The hydroxyl atoms O1 in the molecules at (x, y, z) and (2 - x, 1/2 + y, -z) act as hydrogen-bond donors to atoms O1 at (2 - x, -1/2 + y, -z) and (x, y, z), respectively, so forming a simple C(2) chain (Fig. 2). This chain runs parallel to the shortest crystallographic axis, i.e. axis b, and contains molecules related by the 21 screw axis. There are no interactions between adjacent C(2) chains. However, in the crystal structure of (I) there is also an intermolecular ππ stacking interaction, which involves the C1–C5/C10 (centroid Cg1) and C5–C10 (centroid Cg2) benzene rings (Fig. 2). The perpendicular distances of the ring centroids Cg1 and Cg2 from the planes containing the translation-related centroids Cg2 at (x, -1 + y, z) and Cg1 at (x, 1 + y, z), respectively, are 3.514 (1) and 3.513 (1) Å, and the Cg···Cg separation is 3.610 (1) Å. The planes of rings C1–C5/C10 and C5–C10 make an angle of only 0.437°. These aromatic π-stacking forces are an important factor in the stabilization of the one-dimensional chain in (I). Similarly, as in the cases of (II)–(VI), in order to estimate the area overlap (AO) of adjacent π-stacking molecules, the phenomenological approach proposed by Curtis et al. (2004), in combination with a simple model introduced by Janzen et al. (2004), were used. Analysis of the values of estimated parameters such as the pitch (P) and roll (R) angles, and the pitch (dp) and roll (dr) distances, and the value of AO, indicates that the solid-state packing of (I) provides a substantial overlap between molecules in the π-stack (P = 42.07° > R = 8.95°, dp = 3.18 Å > dr = 0.55 Å, AO = 27.4%). A comparison of the AO value estimated for (I) with the values given in our previous paper (Rozycka-Sokolowska & Marciniak, 2009a) for (II), (III) and (V) (AOII = 27.0%, AOIII = 31.5% and AOV = 40.7%) leads to the conclusion that [as far as the] modification of the molecular structure of (II) by replacement of one H atom at the 4-position by one hydroxy group or one Cl atom results in an increase of this overlap by 4.5 and 13.7%, respectively, then in the case of methoxy substitution, the AO value is only by 0.4% larger than that estimated for (II).

It is noteworthy that the presence of π-stacks with overlap between the adjacent molecules is not a characteristic of the herringbone packing (P < R, dp < dr) in 1,3-, 1,6- and 1,7-naphthalenediols [CSD refcodes: HEGFAB (Marciniak et al., 2006), RIGMOK (Marciniak, 2007b) and LICKEO (Marciniak, 2007a), respectively] and in 2-naphthol [CSD refcode NAPHOB03 (Marciniak et al., 2003)] and its simple derivatives such as (VII), 2,3-, 2,6- and 2,7-naphthalenediols [CSD refcodes: VOGSEP and VOGSAL (Belskii et al., 1990), and NPHLDL01 (Rozycka-Sokolowska et al., 2005), respectively], where apart from strong intermolecular O—H···O hydrogen bonds, there are also weak intermolecular hydrogen bonds of the X—H···π type. In the crystal structures of HEGFAB and LICKEO there are C—H···π hydrogen bonds (see Fig. 3 in Marciniak et al., 2006 and Fig. 4 in Marciniak et al., 2007a, respectively), while in that of RIGMOK there is an interaction of O—H···π type (see Fig.4 in Marciniak, 2007b). The interactions of the C—H···π type also stabilize the crystal structures of NAPHOB03 (Fig. 3), VOGSAL (Fig. 4) and NPHLDL01 (Fig. 5), although this was not discussed in the original reports.

In the crystal structures of (VII) and VOGSEP, however, there are both C—H···π and O—H···π hydrogen bonds (Figs. 6 and 7, respectively), although not previously discussed. Taking into account these facts and bearing in mind that (II) and its derivatives such as (I) and (III)–(VI) yield π-stacking with substantial overlap in the solid state, we may suppose that the parallel arrangement of molecules of these compounds is first of all a consequence of the presence of the substituents at position 1 of the naphthalene moiety and at positions 4 or 5. Moreover, a comparison of the AO values estimated for (II)–(VI) indicates that the overlap between adjacent molecules in the stacks is larger than that estimated for (II) when a substitution at the position 4- takes place [i.e. as in (I), (III) and (V)], while it is smaller when the substituent is at the position 5- [i.e. as in (IV) and (VI)]. Summing up, it is worth noting that in the case of monosubstituted naphthols, the parallel arrangement of the molecules depends on which positions in the naphthalene moiety carry the substituents, while the nature of the substituents, in both 4-substituted and 5-substituted 1-naphthols, determines the extent of the area overlap.

It is also noteworthy that the supramolecular aggregation in (I) is the same as that observed previously for two of its simple analogues, (V) and (II), crystallizing with Z' = 1 in the space groups Pna21 and P21/c, respectively [see Figs. 2 and 3a, respectively, in Rozycka-Sokolowska & Marciniak (2009a)] and it is the simpler than those observed in the crystal structures of three further analogues, namely (III) (Z' = 1/2, Pnma), (IV) (Z' = 1/2, P21/n) and (VI) (Z' = 1, P212121), where sheets containing R44(18) rings were identified [see Fig. 3d in Rozycka-Sokolowska & Marciniak (2009a) and Figs. 2 and 4 in Rozycka-Sokolowska & Marciniak (2009b), respectively]. By contrast with (I), in the structure of the methoxynaphthol isomer (VII) crystallizing with Z`= 1 in the space group P21/c, there are no O—H···O hydrogen bonds or ππ stacking interactions. The herringbone packing of the molecules (VII) is stabilized by three weak hydrogen bonds (Desiraju & Steiner, 1999), one O—H···π(arene) and two C—H···π(arene), although these were not discussed in the original report (Prince et al., 1991). Together these interactions generate a sheet parallel to (100) (Fig. 6).

Related literature top

For related literature, see: Allen & Kirby (1984); Allen et al. (1987); Anthony et al. (2002); Bellows et al. (1978); Belskii et al. (1990); Bolte & Bauch (1998); Chen et al. (2006); Cosmo et al. (1990); Curtis et al. (2004); Flack (1983); Flack & Bernardinelli (2000); Gaultier & Hauw (1967); Horowitz et al. (1996); Janzen et al. (2004); Laquindanum et al. (1997); Li et al. (1998); Marciniak (2007a, 2007b); Marciniak et al. (2003, 2006); Prince et al. (1991); Rozycka-Sokolowska & Marciniak (2009a, 2009b); Rozycka-Sokolowska, Marciniak & Pavlyuk (2004, 2005); Trotter (1986); Wiedenfeld et al. (1999).

Experimental top

Crystals of (I) were grown from a solution in toluene by slow evaporation of solvent at a constant temperature of 293 K.

Refinement top

All C-bound H atoms were included in the refinement at geometrically idealized positions, with C—H distances of 0.93 Å (aromatic) and 0.96 Å (methyl), and with Uiso(H) = 1.2Ueq(Caromatic) or Uiso(H) = 1.5Ueq(Cmethyl). The H atom of the hydroxy group was located in a difference map and refined isotropically, giving an O—H distance of 0.86 (46) Å. In the absence of significant resonant scattering, the Flack (1983) parameter was indeterminate (Flack & Bernardinelli, 2000) and the Friedel equivalent reflections were merged prior to the final refinement.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009), DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the interstack O—H···O hydrogen bond forming a C(2) chain along the [010] direction, and the intrastack ππ interactions. H atoms not involved in hydrogen bonding have been omitted for clarity. Cg1 and Cg2 are the centroids of the C1–C5/C10 and C5–C10 benzene rings, respectively, and are denoted by small spheres. Symmetry codes: (i) -x + 2, -1/2 + y, -z; (ii) x, -1 + y, z; (iii) x, 1 + y, z.
[Figure 3] Fig. 3. Part of the crystal structure of NAPHOB03 (Marciniak et al., 2003), showing a sheet parallel to the (100) plane and formed by the O—H···O (thin dashed lines) and C—H···π (thick dashed lines) hydrogen bonds. All aromatic H atoms not involved in these interactions have been omitted for clarity. Centroids of benzene rings are denoted by small black squares.
[Figure 4] Fig. 4. Part of the crystal structure of VOGSAL (Belskii et al., 1990), showing a three-dimensional framework formed by O—H···O (thin dashed lines) and C—H···π (thick dashed lines) hydrogen bonds. All aromatic H atoms not involved in these interactions have been omitted for clarity. Centroids of benzene rings are denoted by small black spheres.
[Figure 5] Fig. 5. Part of the crystal structure of NPHDL01 (Rozycka-Sokolowska et al., 2005), showing a three-dimensional framework built up from O—H···O (thin dashed lines) and C—H···π (thick dashed lines) hydrogen bonds. All aromatic H atoms not involved in these interactions have been omitted for clarity. Centroids of benzene rings are denoted by small black spheres.
[Figure 6] Fig. 6. Part of the crystal structure of (VII) (Prince et al., 1991), showing a sheet parallel to the (100) plane and formed by the O—H···π (thick grey solid lines) and C—H···π (thick dashed lines) hydrogen bonds. All aromatic H atoms not involved in these interactions have been omitted for clarity. Cg1 and Cg2 are the centroids of aromatic rings, and are denoted by small black spheres.
[Figure 7] Fig. 7. Part of the crystal structure of VOGSEP (Belskii et al., 1990), showing a sheet parallel to the (001) plane and formed by the O—H···O (thin dashed lines), O—H···π (thick grey solid lines) and C—H···π (thick dashed lines) hydrogen bonds. All aromatic H atoms not involved in these interactions have been omitted for clarity.Cg1 and Cg2 are the centroids of aromatic rings, and are denoted by small black spheres.
4-methoxy-1-naphthol top
Crystal data top
C11H10O2F(000) = 184
Mr = 174.19Dx = 1.328 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4896 reflections
a = 8.5940 (4) Åθ = 2.4–26.4°
b = 4.7435 (2) ŵ = 0.09 mm1
c = 10.7293 (5) ÅT = 290 K
β = 95.183 (4)°Column, yellow-brown
V = 435.60 (3) Å30.46 × 0.20 × 0.13 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur3 CCD
diffractometer
994 independent reflections
Radiation source: Enhance (Mo) X-ray Source865 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 26.4°, θmin = 3.2°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)
h = 1010
Tmin = 0.966, Tmax = 1.000k = 55
4893 measured reflectionsl = 1313
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0485P)2 + 0.0226P]
where P = (Fo2 + 2Fc2)/3
994 reflections(Δ/σ)max < 0.001
122 parametersΔρmax = 0.12 e Å3
1 restraintΔρmin = 0.17 e Å3
Crystal data top
C11H10O2V = 435.60 (3) Å3
Mr = 174.19Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.5940 (4) ŵ = 0.09 mm1
b = 4.7435 (2) ÅT = 290 K
c = 10.7293 (5) Å0.46 × 0.20 × 0.13 mm
β = 95.183 (4)°
Data collection top
Oxford Diffraction Xcalibur3 CCD
diffractometer
994 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)
865 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 1.000Rint = 0.024
4893 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0361 restraint
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.12 e Å3
994 reflectionsΔρmin = 0.17 e Å3
122 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
O10.96831 (17)0.0348 (4)0.05823 (15)0.0542 (4)
H10.988 (4)0.186 (8)0.019 (3)0.083 (10)*
O20.42179 (16)0.1312 (5)0.29143 (14)0.0653 (5)
C10.8292 (2)0.0678 (4)0.11263 (17)0.0400 (5)
C20.7149 (2)0.2440 (4)0.06515 (19)0.0445 (5)
H20.72860.34780.00660.053*
C30.5750 (2)0.2709 (5)0.12394 (19)0.0462 (6)
H30.49740.39350.09100.055*
C40.5529 (2)0.1193 (5)0.22817 (18)0.0431 (5)
C50.6702 (2)0.0695 (4)0.28022 (18)0.0392 (5)
C60.6520 (2)0.2308 (5)0.38907 (19)0.0476 (5)
H60.56100.21390.42920.057*
C70.7662 (3)0.4098 (5)0.4352 (2)0.0541 (6)
H70.75160.51780.50560.065*
C80.9054 (3)0.4336 (5)0.3783 (2)0.0552 (6)
H80.98300.55610.41130.066*
C90.9282 (2)0.2786 (4)0.2749 (2)0.0479 (6)
H91.02220.29380.23860.057*
C100.8111 (2)0.0949 (4)0.22184 (18)0.0376 (5)
C110.3053 (3)0.3307 (8)0.2489 (2)0.0712 (8)
H11A0.21950.31900.30010.107*
H11B0.34890.51710.25440.107*
H11C0.26890.29050.16350.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0482 (8)0.0534 (10)0.0650 (10)0.0044 (8)0.0267 (7)0.0048 (8)
O20.0481 (8)0.0863 (12)0.0649 (9)0.0226 (9)0.0245 (7)0.0171 (10)
C10.0389 (9)0.0393 (12)0.0432 (11)0.0049 (11)0.0113 (8)0.0094 (11)
C20.0474 (10)0.0448 (14)0.0419 (11)0.0014 (11)0.0069 (9)0.0025 (10)
C30.0427 (10)0.0498 (14)0.0458 (11)0.0082 (11)0.0027 (9)0.0021 (11)
C40.0369 (10)0.0499 (13)0.0435 (11)0.0064 (11)0.0087 (8)0.0039 (11)
C50.0407 (9)0.0398 (12)0.0374 (10)0.0025 (9)0.0053 (8)0.0058 (10)
C60.0495 (11)0.0524 (14)0.0425 (11)0.0021 (11)0.0125 (9)0.0000 (11)
C70.0697 (13)0.0522 (15)0.0405 (11)0.0041 (13)0.0052 (10)0.0052 (12)
C80.0588 (12)0.0531 (15)0.0529 (12)0.0157 (12)0.0001 (10)0.0021 (12)
C90.0451 (10)0.0465 (14)0.0528 (12)0.0088 (11)0.0085 (9)0.0060 (11)
C100.0365 (9)0.0359 (11)0.0404 (10)0.0007 (9)0.0046 (8)0.0097 (9)
C110.0478 (12)0.094 (2)0.0737 (16)0.0268 (15)0.0156 (11)0.0087 (16)
Geometric parameters (Å, º) top
O1—C11.386 (2)C5—C101.418 (2)
O1—H10.86 (4)C6—C71.357 (3)
O2—C41.368 (2)C6—H60.9300
O2—C111.422 (3)C7—C81.396 (3)
C1—C21.353 (3)C7—H70.9300
C1—C101.423 (3)C8—C91.360 (3)
C2—C31.413 (3)C8—H80.9300
C2—H20.9300C9—C101.411 (3)
C3—C41.357 (3)C9—H90.9300
C3—H30.9300C11—H11A0.9600
C4—C51.424 (3)C11—H11B0.9600
C5—C61.417 (3)C11—H11C0.9600
C1—O1—H1109 (2)C5—C6—H6119.7
C4—O2—C11117.13 (18)C6—C7—C8120.7 (2)
C2—C1—O1122.37 (18)C6—C7—H7119.6
C2—C1—C10121.02 (16)C8—C7—H7119.6
O1—C1—C10116.61 (17)C9—C8—C7120.4 (2)
C1—C2—C3120.36 (19)C9—C8—H8119.8
C1—C2—H2119.8C7—C8—H8119.8
C3—C2—H2119.8C8—C9—C10120.83 (18)
C4—C3—C2120.52 (19)C8—C9—H9119.6
C4—C3—H3119.7C10—C9—H9119.6
C2—C3—H3119.7C9—C10—C5118.73 (17)
C3—C4—O2124.72 (18)C9—C10—C1122.67 (16)
C3—C4—C5120.64 (16)C5—C10—C1118.60 (16)
O2—C4—C5114.64 (16)O2—C11—H11A109.5
C6—C5—C10118.73 (17)O2—C11—H11B109.5
C6—C5—C4122.41 (17)H11A—C11—H11B109.5
C10—C5—C4118.86 (16)O2—C11—H11C109.5
C7—C6—C5120.57 (18)H11A—C11—H11C109.5
C7—C6—H6119.7H11B—C11—H11C109.5
O1—C1—C2—C3179.93 (19)C5—C6—C7—C81.6 (3)
C10—C1—C2—C30.3 (3)C6—C7—C8—C90.5 (3)
C1—C2—C3—C40.4 (3)C7—C8—C9—C101.1 (3)
C2—C3—C4—O2180.0 (2)C8—C9—C10—C51.5 (3)
C2—C3—C4—C50.0 (3)C8—C9—C10—C1179.0 (2)
C11—O2—C4—C34.2 (3)C6—C5—C10—C90.4 (3)
C11—O2—C4—C5175.7 (2)C4—C5—C10—C9178.9 (2)
C3—C4—C5—C6179.8 (2)C6—C5—C10—C1179.90 (19)
O2—C4—C5—C60.2 (3)C4—C5—C10—C10.6 (2)
C3—C4—C5—C100.5 (3)C2—C1—C10—C9179.32 (19)
O2—C4—C5—C10179.48 (18)O1—C1—C10—C90.9 (3)
C10—C5—C6—C71.1 (3)C2—C1—C10—C50.2 (3)
C4—C5—C6—C7179.6 (2)O1—C1—C10—C5179.58 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.86 (4)1.90 (4)2.758 (2)176 (3)
Symmetry code: (i) x+2, y1/2, z.

Experimental details

Crystal data
Chemical formulaC11H10O2
Mr174.19
Crystal system, space groupMonoclinic, P21
Temperature (K)290
a, b, c (Å)8.5940 (4), 4.7435 (2), 10.7293 (5)
β (°) 95.183 (4)
V3)435.60 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.46 × 0.20 × 0.13
Data collection
DiffractometerOxford Diffraction Xcalibur3 CCD
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2008)
Tmin, Tmax0.966, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
4893, 994, 865
Rint0.024
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.084, 1.03
No. of reflections994
No. of parameters122
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.12, 0.17

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Selected bond lengths (Å) top
O1—C11.386 (2)C4—C51.424 (3)
O2—C41.368 (2)C5—C61.417 (3)
O2—C111.422 (3)C5—C101.418 (2)
C1—C21.353 (3)C6—C71.357 (3)
C1—C101.423 (3)C7—C81.396 (3)
C2—C31.413 (3)C8—C91.360 (3)
C3—C41.357 (3)C9—C101.411 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.86 (4)1.90 (4)2.758 (2)176 (3)
Symmetry code: (i) x+2, y1/2, z.
 

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