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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(2E)-3-(2-Anthracen-2-yl)-1-(2-hy­dr­oxy­phen­yl)prop-2-en-1-one

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, cDepartment of Chemistry, P.A. College of Engineering, Mangalore, 574 153, India, and dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 3 February 2011; accepted 28 February 2011; online 5 March 2011)

The asymmetric unit of the title compound, C23H16O2, contains two independent mol­ecules in which the dihedral angles between the anthracene ring system and the benzene ring are 73.0 (3) and 73.3 (3)°. In both independent mol­ecules, the hy­droxy group is involved in an intra­molecular O—H⋯O hydrogen bond. The crystal packing is stabilized by ππ inter­actions [centroid–centroid distances = 3.6518 (9), 3.7070 (9) and 3.7632 (9) Å] and weak inter­molecular C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Chantrapromma et al. (2009[Chantrapromma, S., Horkaew, J., Suwunwong, T. & Fun, H.-K. (2009). Acta Cryst. E65, o2673-o2674.]); Jasinski et al. (2010[Jasinski, J. P., Butcher, R. J., Chidan Kumar, C. S., Yathirajan, H. S. & Mayekar, A. N. (2010). Acta Cryst. E66, o2936-o2937.], 2011a[Jasinski, J. P., Butcher, R. J., Siddaraju, B. P., Narayana, B. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o313-o314.],b[Jasinski, J. P., Butcher, R. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o352-o353.]); Lu et al. (2009[Lu, Y.-H., Wang, G.-Z., Zhou, C.-H. & Zhang, Y.-Y. (2009). Acta Cryst. E65, o1396.]); Suwunwong et al. (2009[Suwunwong, T., Chantrapromma, S., Karalai, C., Pakdeevanich, P. & Fun, H.-K. (2009). Acta Cryst. E65, o420-o421.]); Wang et al. (2009[Wang, G.-Z., Fang, B. & Zhou, C.-H. (2009). Acta Cryst. E65, o2619.], 2010[Wang, X.-L., Wang, G.-Z., Geng, R.-X. & Zhou, C.-H. (2010). Acta Cryst. E66, o320.]).

[Scheme 1]

Experimental

Crystal data
  • C23H16O2

  • Mr = 324.36

  • Monoclinic, P 21 /c

  • a = 14.0748 (5) Å

  • b = 13.7362 (5) Å

  • c = 16.9800 (8) Å

  • β = 101.487 (5)°

  • V = 3217.1 (2) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.67 mm−1

  • T = 110 K

  • 0.46 × 0.35 × 0.16 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.530, Tmax = 1.000

  • 14048 measured reflections

  • 6371 independent reflections

  • 5277 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.134

  • S = 1.06

  • 6371 reflections

  • 453 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1A—H1A⋯O2A 0.84 1.83 2.5729 (15) 146
O1B—H1B⋯O2B 0.84 1.80 2.5452 (16) 146
C14B—H14B⋯O1Bi 0.95 2.60 3.537 (2) 169
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In continuation to our studies on crystal structures of chalcones (Jasinski et al. 2010, 2011a, b) we report here the synthesis and crystal structure of the title compound, (I).

The asymmetric unit of (I) contains two independent molecules, A & B, respectively (Fig. 1). The dihedral angles between the mean planes of the 2-anthryl and benzene rings are 73.0 (9)° and 73.3 (3)° in A and B, respectively. Bond lengths and angles are normal and correspond to those observed in the related compounds ((Z)-3-(9-anthryl)-1-(4-methoxyphenyl) prop-2-en-1-one (Chantrapromma et al., 2009), (E)-3-(anthracen-9-yl)-1-(4-bromophenyl)prop-2-en-1-one (Suwunwong et al., 2009), (Z)-3-(9-anthryl)-1-(4-bromophenyl)-2-(4-nitro-1H-imidazol-1-yl) prop-2-en-1-one (Lu et al., 2009), (Z)-3-(9-anthryl)-2-(4-nitro-1H-imidazol-1-yl)-1-p-tolylprop-2-en-1-one (Wang et al., 2009) and (E)-3-(9-anthryl)-1-(4-fluorophenyl)-2-(4-nitro-1H-imidazol-1-yl) prop-2-en-1-one (Wang et al., 2010).

Crystal packing (Fig. 2) is stabilized by ππ stacking interactions (Table 1) and weak intramolecular C—H···O hydrogen bonds (Table 2).

Related literature top

For related structures, see: Chantrapromma et al. (2009); Jasinski et al. (2010, 2011a,b); Lu et al. (2009); Suwunwong et al. (2009); Wang et al. (2009, 2010).

Experimental top

2-Hydroxyacetophenone (1.36 g, 0.01 mol) was mixed with 2- anthraldehyde (2.06 g, 0.01 mol) and dissolved in ethanol (40 ml). To this solution, 5 ml of KOH (50%) was added at 278 K. The reaction mixture stirred for 6 h and poured on to crushed ice (Fig. 3). The pH of this mixture was adjusted to 3–4 with 2 M HCl aqueous solution. The resulting crude yellow solid was filtered, washed successively with dilute HCl solution and distilled water and finally recrystallized from ethanol (95%) to give the pure chalcone. Crystals suitable for x-ray diffraction studies were grown by the slow evaporation of the solution of the compound in ethyl alcohol (m.p.: 393 K). Composition: Found (Calculated) for C23H16O2, C: 85.09 (85.16); H: 4.95 (4.97).

Refinement top

Atoms H1A and H1B were located on a Fourier map, and placed in idealized positions with O—H 0.84 Å. C-bound H atoms were placed in calculated positions (C—-H 0.95Å). All H atoms were refined as riding, with Uiso(H) = 1.2 Ueq of the parent atom.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Two independent molecules of (I) showing the atom labeling scheme and 50% probability displacement ellipsoids. Dashed lines indicate intramolecular O—H···O hydrogen bonds.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed down the a axis. Dashed lines indicate intramolecular O—H···O hydrogen bonds.
[Figure 3] Fig. 3. Reaction scheme for (I).
(2E)-3-(2-Anthracen-2-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one top
Crystal data top
C23H16O2F(000) = 1360
Mr = 324.36Dx = 1.339 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 7472 reflections
a = 14.0748 (5) Åθ = 4.5–74.2°
b = 13.7362 (5) ŵ = 0.67 mm1
c = 16.9800 (8) ÅT = 110 K
β = 101.487 (5)°Plate, pale yellow
V = 3217.1 (2) Å30.46 × 0.35 × 0.16 mm
Z = 8
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Ruby (Gemini Cu) detector
6371 independent reflections
Radiation source: Enhance (Cu) X-ray Source5277 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 10.5081 pixels mm-1θmax = 74.3°, θmin = 4.5°
ω scansh = 1717
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 1316
Tmin = 0.530, Tmax = 1.000l = 2117
14048 measured reflections
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.082P)2 + 0.651P]
where P = (Fo2 + 2Fc2)/3
6371 reflections(Δ/σ)max = 0.001
453 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C23H16O2V = 3217.1 (2) Å3
Mr = 324.36Z = 8
Monoclinic, P21/cCu Kα radiation
a = 14.0748 (5) ŵ = 0.67 mm1
b = 13.7362 (5) ÅT = 110 K
c = 16.9800 (8) Å0.46 × 0.35 × 0.16 mm
β = 101.487 (5)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Ruby (Gemini Cu) detector
6371 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
5277 reflections with I > 2σ(I)
Tmin = 0.530, Tmax = 1.000Rint = 0.022
14048 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.134H-atom parameters constrained
S = 1.06Δρmax = 0.30 e Å3
6371 reflectionsΔρmin = 0.24 e Å3
453 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
O1A0.96585 (8)0.60784 (8)0.83860 (7)0.0324 (3)
H1A0.92100.57100.81600.039*
O2A0.81576 (8)0.55812 (8)0.73334 (7)0.0331 (3)
C1A0.88430 (10)0.71509 (11)0.73290 (8)0.0240 (3)
C2A0.95647 (10)0.69567 (11)0.80224 (9)0.0261 (3)
C3A1.02217 (10)0.76822 (13)0.83456 (9)0.0303 (3)
H3AA1.07070.75470.88070.036*
C4A1.01718 (11)0.85966 (12)0.79998 (10)0.0319 (3)
H4AA1.06210.90860.82260.038*
C5A0.94648 (11)0.88039 (12)0.73208 (10)0.0312 (3)
H5AA0.94290.94340.70850.037*
C6A0.88169 (10)0.80891 (11)0.69930 (9)0.0264 (3)
H6AA0.83400.82340.65280.032*
C7A0.81576 (10)0.63764 (11)0.69853 (9)0.0255 (3)
C8A0.74674 (11)0.65488 (11)0.62179 (9)0.0262 (3)
H8AA0.75820.70720.58830.031*
C9A0.66916 (10)0.59885 (10)0.59865 (9)0.0244 (3)
H9AA0.65970.54660.63290.029*
C10A0.59645 (10)0.61196 (10)0.52339 (9)0.0233 (3)
C11A0.49737 (10)0.62045 (10)0.52774 (9)0.0230 (3)
C12A0.46396 (11)0.61652 (11)0.60210 (9)0.0273 (3)
H12A0.50970.60730.65080.033*
C13A0.36839 (12)0.62563 (11)0.60448 (10)0.0300 (3)
H13A0.34840.62210.65460.036*
C14A0.29797 (11)0.64039 (12)0.53282 (10)0.0309 (3)
H14A0.23140.64670.53540.037*
C15A0.32575 (11)0.64553 (11)0.46082 (10)0.0278 (3)
H15A0.27830.65550.41320.033*
C16A0.42598 (10)0.63611 (10)0.45561 (9)0.0242 (3)
C17A0.45523 (11)0.64314 (10)0.38216 (9)0.0251 (3)
H17A0.40780.65350.33460.030*
C18A0.55268 (11)0.63533 (10)0.37680 (9)0.0247 (3)
C19A0.58188 (12)0.64459 (12)0.30104 (9)0.0307 (3)
H19A0.53440.65770.25410.037*
C20A0.67614 (12)0.63502 (13)0.29520 (10)0.0342 (4)
H20A0.69440.64270.24460.041*
C21A0.74762 (11)0.61345 (12)0.36476 (10)0.0320 (4)
H21A0.81330.60510.36010.038*
C22A0.72298 (11)0.60470 (11)0.43796 (9)0.0276 (3)
H22A0.77190.58970.48350.033*
C23A0.62502 (10)0.61761 (10)0.44803 (9)0.0239 (3)
O1B0.87649 (8)0.37852 (9)0.86203 (7)0.0357 (3)
H1B0.83380.37370.81990.043*
O2B0.76730 (8)0.29254 (8)0.74519 (7)0.0326 (3)
C1B0.88557 (10)0.20563 (12)0.83681 (9)0.0264 (3)
C2B0.91401 (11)0.29000 (12)0.88336 (9)0.0296 (3)
C3B0.98406 (11)0.28300 (14)0.95397 (10)0.0348 (4)
H3BA1.00150.33900.98640.042*
C4B1.02796 (12)0.19501 (14)0.97663 (10)0.0363 (4)
H4BA1.07620.19121.02440.044*
C5B1.00302 (12)0.11175 (13)0.93085 (10)0.0344 (4)
H5BA1.03470.05170.94660.041*
C6B0.93192 (11)0.11713 (12)0.86238 (10)0.0302 (3)
H6BA0.91380.05980.83170.036*
C7B0.80797 (10)0.21316 (12)0.76505 (9)0.0271 (3)
C8B0.77549 (11)0.12518 (12)0.71763 (9)0.0296 (3)
H8BA0.81640.06960.72220.035*
C9B0.68909 (11)0.12307 (12)0.66833 (9)0.0276 (3)
H9BA0.65120.18080.66350.033*
C10B0.64816 (10)0.03859 (11)0.62117 (8)0.0245 (3)
C11B0.55384 (10)0.00678 (11)0.62741 (8)0.0261 (3)
C12B0.49770 (11)0.05492 (13)0.67701 (9)0.0327 (4)
H12B0.52310.11100.70670.039*
C13B0.40761 (12)0.02110 (15)0.68231 (10)0.0391 (4)
H13B0.37090.05460.71510.047*
C14B0.36860 (11)0.06279 (15)0.63980 (10)0.0397 (4)
H14B0.30640.08580.64480.048*
C15B0.41931 (12)0.11068 (13)0.59188 (10)0.0344 (4)
H15B0.39200.16670.56320.041*
C16B0.51345 (11)0.07794 (12)0.58384 (9)0.0278 (3)
C17B0.56580 (11)0.12588 (11)0.53403 (9)0.0285 (3)
H17B0.53850.18170.50500.034*
C18B0.65734 (11)0.09390 (11)0.52567 (9)0.0261 (3)
C19B0.70820 (12)0.14151 (11)0.47156 (10)0.0309 (3)
H19B0.67990.19650.44200.037*
C20B0.79625 (12)0.10940 (12)0.46176 (10)0.0327 (3)
H20B0.82940.14220.42600.039*
C21B0.83880 (11)0.02683 (12)0.50492 (9)0.0312 (3)
H21B0.90030.00450.49740.037*
C22B0.79310 (11)0.02095 (11)0.55691 (9)0.0269 (3)
H22B0.82300.07630.58490.032*
C23B0.70031 (10)0.01093 (11)0.57023 (8)0.0241 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0283 (6)0.0336 (6)0.0318 (6)0.0002 (4)0.0021 (4)0.0019 (5)
O2A0.0317 (6)0.0280 (6)0.0355 (6)0.0025 (4)0.0032 (5)0.0049 (5)
C1A0.0196 (6)0.0293 (7)0.0236 (6)0.0005 (5)0.0057 (5)0.0032 (6)
C2A0.0222 (7)0.0322 (8)0.0250 (7)0.0026 (6)0.0073 (6)0.0021 (6)
C3A0.0217 (7)0.0432 (9)0.0252 (7)0.0005 (6)0.0023 (6)0.0063 (6)
C4A0.0258 (7)0.0364 (9)0.0338 (8)0.0072 (6)0.0066 (6)0.0118 (7)
C5A0.0299 (8)0.0297 (8)0.0346 (8)0.0020 (6)0.0081 (6)0.0036 (6)
C6A0.0228 (7)0.0312 (8)0.0253 (7)0.0003 (6)0.0047 (5)0.0023 (6)
C7A0.0225 (7)0.0264 (7)0.0273 (7)0.0015 (6)0.0041 (6)0.0010 (6)
C8A0.0258 (7)0.0246 (7)0.0271 (7)0.0002 (6)0.0025 (6)0.0008 (6)
C9A0.0252 (7)0.0213 (7)0.0261 (7)0.0006 (5)0.0038 (6)0.0004 (6)
C10A0.0240 (7)0.0163 (6)0.0285 (7)0.0019 (5)0.0024 (6)0.0017 (5)
C11A0.0244 (7)0.0168 (6)0.0270 (7)0.0029 (5)0.0029 (6)0.0013 (5)
C12A0.0287 (7)0.0240 (7)0.0280 (7)0.0016 (6)0.0030 (6)0.0003 (6)
C13A0.0320 (8)0.0285 (8)0.0314 (8)0.0018 (6)0.0107 (6)0.0003 (6)
C14A0.0237 (7)0.0294 (8)0.0403 (8)0.0007 (6)0.0075 (6)0.0012 (7)
C15A0.0223 (7)0.0252 (7)0.0339 (8)0.0007 (6)0.0012 (6)0.0011 (6)
C16A0.0227 (7)0.0178 (6)0.0309 (7)0.0021 (5)0.0027 (6)0.0020 (5)
C17A0.0245 (7)0.0212 (7)0.0267 (7)0.0017 (5)0.0018 (6)0.0021 (6)
C18A0.0263 (7)0.0204 (7)0.0266 (7)0.0037 (5)0.0035 (6)0.0047 (5)
C19A0.0312 (8)0.0327 (8)0.0263 (7)0.0053 (6)0.0016 (6)0.0043 (6)
C20A0.0347 (8)0.0413 (9)0.0281 (8)0.0080 (7)0.0102 (7)0.0084 (7)
C21A0.0250 (7)0.0342 (8)0.0373 (8)0.0043 (6)0.0077 (6)0.0106 (7)
C22A0.0244 (7)0.0250 (7)0.0321 (7)0.0023 (6)0.0024 (6)0.0063 (6)
C23A0.0231 (7)0.0189 (7)0.0286 (7)0.0033 (5)0.0024 (6)0.0044 (5)
O1B0.0278 (6)0.0360 (6)0.0401 (6)0.0039 (5)0.0006 (5)0.0118 (5)
O2B0.0275 (5)0.0310 (6)0.0367 (6)0.0024 (4)0.0001 (5)0.0045 (5)
C1B0.0210 (7)0.0344 (8)0.0246 (7)0.0022 (6)0.0063 (6)0.0017 (6)
C2B0.0220 (7)0.0361 (8)0.0320 (8)0.0001 (6)0.0088 (6)0.0051 (7)
C3B0.0271 (8)0.0438 (9)0.0318 (8)0.0018 (7)0.0021 (6)0.0114 (7)
C4B0.0279 (8)0.0532 (11)0.0264 (7)0.0004 (7)0.0016 (6)0.0002 (7)
C5B0.0316 (8)0.0383 (9)0.0325 (8)0.0007 (7)0.0046 (7)0.0076 (7)
C6B0.0295 (8)0.0302 (8)0.0310 (7)0.0039 (6)0.0062 (6)0.0011 (6)
C7B0.0216 (7)0.0310 (8)0.0295 (7)0.0001 (6)0.0070 (6)0.0009 (6)
C8B0.0275 (7)0.0296 (8)0.0305 (7)0.0011 (6)0.0031 (6)0.0030 (6)
C9B0.0248 (7)0.0291 (8)0.0287 (7)0.0007 (6)0.0049 (6)0.0011 (6)
C10B0.0222 (7)0.0263 (7)0.0228 (6)0.0013 (5)0.0008 (5)0.0040 (6)
C11B0.0221 (7)0.0307 (8)0.0233 (7)0.0005 (6)0.0007 (5)0.0074 (6)
C12B0.0256 (7)0.0459 (10)0.0249 (7)0.0004 (7)0.0004 (6)0.0030 (7)
C13B0.0252 (8)0.0647 (12)0.0275 (8)0.0051 (8)0.0050 (6)0.0101 (8)
C14B0.0209 (7)0.0589 (12)0.0373 (9)0.0066 (7)0.0010 (7)0.0189 (8)
C15B0.0261 (8)0.0360 (9)0.0374 (8)0.0083 (6)0.0023 (6)0.0133 (7)
C16B0.0236 (7)0.0281 (8)0.0286 (7)0.0039 (6)0.0020 (6)0.0107 (6)
C17B0.0288 (8)0.0212 (7)0.0311 (7)0.0046 (6)0.0044 (6)0.0053 (6)
C18B0.0269 (7)0.0205 (7)0.0284 (7)0.0007 (6)0.0007 (6)0.0053 (6)
C19B0.0363 (8)0.0219 (7)0.0316 (8)0.0030 (6)0.0000 (6)0.0004 (6)
C20B0.0349 (8)0.0305 (8)0.0328 (8)0.0075 (7)0.0071 (7)0.0002 (6)
C21B0.0264 (7)0.0335 (8)0.0341 (8)0.0011 (6)0.0065 (6)0.0051 (7)
C22B0.0241 (7)0.0254 (7)0.0298 (7)0.0030 (6)0.0021 (6)0.0021 (6)
C23B0.0229 (7)0.0225 (7)0.0247 (7)0.0002 (5)0.0002 (6)0.0051 (6)
Geometric parameters (Å, º) top
O1A—C2A1.3498 (19)O1B—C2B1.346 (2)
O1A—H1A0.8400O1B—H1B0.8400
O2A—C7A1.2420 (19)O2B—C7B1.2464 (19)
C1A—C6A1.407 (2)C1B—C6B1.407 (2)
C1A—C2A1.419 (2)C1B—C2B1.415 (2)
C1A—C7A1.476 (2)C1B—C7B1.469 (2)
C2A—C3A1.395 (2)C2B—C3B1.396 (2)
C3A—C4A1.382 (2)C3B—C4B1.377 (3)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.394 (2)C4B—C5B1.388 (3)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.380 (2)C5B—C6B1.377 (2)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—H6AA0.9500C6B—H6BA0.9500
C7A—C8A1.481 (2)C7B—C8B1.473 (2)
C8A—C9A1.330 (2)C8B—C9B1.332 (2)
C8A—H8AA0.9500C8B—H8BA0.9500
C9A—C10A1.481 (2)C9B—C10B1.461 (2)
C9A—H9AA0.9500C9B—H9BA0.9500
C10A—C11A1.416 (2)C10B—C23B1.415 (2)
C10A—C23A1.418 (2)C10B—C11B1.421 (2)
C11A—C12A1.433 (2)C11B—C12B1.427 (2)
C11A—C16A1.437 (2)C11B—C16B1.434 (2)
C12A—C13A1.360 (2)C12B—C13B1.370 (2)
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.423 (2)C13B—C14B1.412 (3)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.358 (2)C14B—C15B1.355 (3)
C14A—H14A0.9500C14B—H14B0.9500
C15A—C16A1.437 (2)C15B—C16B1.431 (2)
C15A—H15A0.9500C15B—H15B0.9500
C16A—C17A1.392 (2)C16B—C17B1.393 (2)
C17A—C18A1.397 (2)C17B—C18B1.395 (2)
C17A—H17A0.9500C17B—H17B0.9500
C18A—C19A1.432 (2)C18B—C19B1.430 (2)
C18A—C23A1.438 (2)C18B—C23B1.434 (2)
C19A—C20A1.356 (2)C19B—C20B1.357 (2)
C19A—H19A0.9500C19B—H19B0.9500
C20A—C21A1.422 (2)C20B—C21B1.417 (2)
C20A—H20A0.9500C20B—H20B0.9500
C21A—C22A1.361 (2)C21B—C22B1.360 (2)
C21A—H21A0.9500C21B—H21B0.9500
C22A—C23A1.434 (2)C22B—C23B1.437 (2)
C22A—H22A0.9500C22B—H22B0.9500
Cg1···Cg4i3.652 (2)Cg5···Cg5iii3.763 (2)
Cg2···Cg3ii3.707 (2)
C2A—O1A—H1A109.5C2B—O1B—H1B109.5
C6A—C1A—C2A117.73 (14)C6B—C1B—C2B118.24 (14)
C6A—C1A—C7A122.52 (13)C6B—C1B—C7B122.64 (14)
C2A—C1A—C7A119.75 (14)C2B—C1B—C7B119.11 (14)
O1A—C2A—C3A117.49 (13)O1B—C2B—C3B117.74 (15)
O1A—C2A—C1A122.44 (14)O1B—C2B—C1B122.51 (14)
C3A—C2A—C1A120.06 (14)C3B—C2B—C1B119.75 (15)
C4A—C3A—C2A120.55 (14)C4B—C3B—C2B120.10 (16)
C4A—C3A—H3AA119.7C4B—C3B—H3BA119.9
C2A—C3A—H3AA119.7C2B—C3B—H3BA119.9
C3A—C4A—C5A120.29 (14)C3B—C4B—C5B121.15 (15)
C3A—C4A—H4AA119.9C3B—C4B—H4BA119.4
C5A—C4A—H4AA119.9C5B—C4B—H4BA119.4
C6A—C5A—C4A119.60 (15)C6B—C5B—C4B119.27 (16)
C6A—C5A—H5AA120.2C6B—C5B—H5BA120.4
C4A—C5A—H5AA120.2C4B—C5B—H5BA120.4
C5A—C6A—C1A121.77 (14)C5B—C6B—C1B121.44 (15)
C5A—C6A—H6AA119.1C5B—C6B—H6BA119.3
C1A—C6A—H6AA119.1C1B—C6B—H6BA119.3
O2A—C7A—C1A120.50 (13)O2B—C7B—C1B120.76 (14)
O2A—C7A—C8A119.82 (14)O2B—C7B—C8B119.60 (13)
C1A—C7A—C8A119.68 (13)C1B—C7B—C8B119.60 (14)
C9A—C8A—C7A121.57 (14)C9B—C8B—C7B120.42 (14)
C9A—C8A—H8AA119.2C9B—C8B—H8BA119.8
C7A—C8A—H8AA119.2C7B—C8B—H8BA119.8
C8A—C9A—C10A124.78 (14)C8B—C9B—C10B124.92 (15)
C8A—C9A—H9AA117.6C8B—C9B—H9BA117.5
C10A—C9A—H9AA117.6C10B—C9B—H9BA117.5
C11A—C10A—C23A120.13 (13)C23B—C10B—C11B120.24 (14)
C11A—C10A—C9A118.93 (13)C23B—C10B—C9B121.38 (13)
C23A—C10A—C9A120.94 (13)C11B—C10B—C9B118.38 (13)
C10A—C11A—C12A122.82 (13)C10B—C11B—C12B122.46 (15)
C10A—C11A—C16A119.77 (13)C10B—C11B—C16B119.41 (14)
C12A—C11A—C16A117.39 (13)C12B—C11B—C16B118.12 (14)
C13A—C12A—C11A121.52 (14)C13B—C12B—C11B120.68 (17)
C13A—C12A—H12A119.2C13B—C12B—H12B119.7
C11A—C12A—H12A119.2C11B—C12B—H12B119.7
C12A—C13A—C14A120.84 (14)C12B—C13B—C14B120.93 (17)
C12A—C13A—H13A119.6C12B—C13B—H13B119.5
C14A—C13A—H13A119.6C14B—C13B—H13B119.5
C15A—C14A—C13A120.07 (14)C15B—C14B—C13B120.38 (15)
C15A—C14A—H14A120.0C15B—C14B—H14B119.8
C13A—C14A—H14A120.0C13B—C14B—H14B119.8
C14A—C15A—C16A120.88 (14)C14B—C15B—C16B120.87 (16)
C14A—C15A—H15A119.6C14B—C15B—H15B119.6
C16A—C15A—H15A119.6C16B—C15B—H15B119.6
C17A—C16A—C15A121.20 (14)C17B—C16B—C15B121.40 (15)
C17A—C16A—C11A119.50 (13)C17B—C16B—C11B119.58 (14)
C15A—C16A—C11A119.30 (14)C15B—C16B—C11B119.02 (15)
C16A—C17A—C18A121.50 (13)C16B—C17B—C18B121.59 (14)
C16A—C17A—H17A119.3C16B—C17B—H17B119.2
C18A—C17A—H17A119.3C18B—C17B—H17B119.2
C17A—C18A—C19A120.86 (14)C17B—C18B—C19B120.79 (14)
C17A—C18A—C23A119.88 (13)C17B—C18B—C23B119.85 (14)
C19A—C18A—C23A119.26 (13)C19B—C18B—C23B119.34 (14)
C20A—C19A—C18A121.13 (15)C20B—C19B—C18B121.09 (15)
C20A—C19A—H19A119.4C20B—C19B—H19B119.5
C18A—C19A—H19A119.4C18B—C19B—H19B119.5
C19A—C20A—C21A120.00 (15)C19B—C20B—C21B119.95 (15)
C19A—C20A—H20A120.0C19B—C20B—H20B120.0
C21A—C20A—H20A120.0C21B—C20B—H20B120.0
C22A—C21A—C20A120.69 (14)C22B—C21B—C20B121.08 (15)
C22A—C21A—H21A119.7C22B—C21B—H21B119.5
C20A—C21A—H21A119.7C20B—C21B—H21B119.5
C21A—C22A—C23A121.61 (14)C21B—C22B—C23B121.14 (14)
C21A—C22A—H22A119.2C21B—C22B—H22B119.4
C23A—C22A—H22A119.2C23B—C22B—H22B119.4
C10A—C23A—C22A123.59 (14)C10B—C23B—C18B119.28 (13)
C10A—C23A—C18A119.19 (13)C10B—C23B—C22B123.23 (14)
C22A—C23A—C18A117.21 (13)C18B—C23B—C22B117.40 (13)
C6A—C1A—C2A—O1A179.30 (13)C6B—C1B—C2B—O1B177.39 (14)
C7A—C1A—C2A—O1A0.4 (2)C7B—C1B—C2B—O1B3.8 (2)
C6A—C1A—C2A—C3A0.4 (2)C6B—C1B—C2B—C3B2.1 (2)
C7A—C1A—C2A—C3A179.31 (13)C7B—C1B—C2B—C3B176.67 (13)
O1A—C2A—C3A—C4A179.54 (13)O1B—C2B—C3B—C4B177.06 (15)
C1A—C2A—C3A—C4A0.6 (2)C1B—C2B—C3B—C4B2.5 (2)
C2A—C3A—C4A—C5A0.2 (2)C2B—C3B—C4B—C5B0.8 (3)
C3A—C4A—C5A—C6A0.3 (2)C3B—C4B—C5B—C6B1.2 (2)
C4A—C5A—C6A—C1A0.5 (2)C4B—C5B—C6B—C1B1.5 (2)
C2A—C1A—C6A—C5A0.1 (2)C2B—C1B—C6B—C5B0.1 (2)
C7A—C1A—C6A—C5A179.83 (14)C7B—C1B—C6B—C5B178.59 (14)
C6A—C1A—C7A—O2A174.60 (14)C6B—C1B—C7B—O2B178.57 (14)
C2A—C1A—C7A—O2A5.7 (2)C2B—C1B—C7B—O2B0.1 (2)
C6A—C1A—C7A—C8A5.6 (2)C6B—C1B—C7B—C8B0.7 (2)
C2A—C1A—C7A—C8A174.06 (12)C2B—C1B—C7B—C8B177.97 (13)
O2A—C7A—C8A—C9A17.1 (2)O2B—C7B—C8B—C9B17.9 (2)
C1A—C7A—C8A—C9A163.12 (14)C1B—C7B—C8B—C9B159.94 (14)
C7A—C8A—C9A—C10A179.36 (13)C7B—C8B—C9B—C10B177.36 (14)
C8A—C9A—C10A—C11A125.78 (16)C8B—C9B—C10B—C23B52.8 (2)
C8A—C9A—C10A—C23A53.2 (2)C8B—C9B—C10B—C11B127.28 (17)
C23A—C10A—C11A—C12A179.24 (13)C23B—C10B—C11B—C12B179.11 (14)
C9A—C10A—C11A—C12A0.3 (2)C9B—C10B—C11B—C12B0.8 (2)
C23A—C10A—C11A—C16A0.8 (2)C23B—C10B—C11B—C16B2.2 (2)
C9A—C10A—C11A—C16A178.16 (13)C9B—C10B—C11B—C16B177.89 (13)
C10A—C11A—C12A—C13A179.50 (14)C10B—C11B—C12B—C13B179.02 (14)
C16A—C11A—C12A—C13A1.0 (2)C16B—C11B—C12B—C13B0.3 (2)
C11A—C12A—C13A—C14A0.6 (2)C11B—C12B—C13B—C14B0.8 (2)
C12A—C13A—C14A—C15A0.0 (2)C12B—C13B—C14B—C15B1.0 (3)
C13A—C14A—C15A—C16A0.1 (2)C13B—C14B—C15B—C16B0.5 (2)
C14A—C15A—C16A—C17A178.77 (14)C14B—C15B—C16B—C17B179.23 (15)
C14A—C15A—C16A—C11A0.4 (2)C14B—C15B—C16B—C11B0.0 (2)
C10A—C11A—C16A—C17A0.3 (2)C10B—C11B—C16B—C17B2.1 (2)
C12A—C11A—C16A—C17A178.26 (13)C12B—C11B—C16B—C17B179.13 (14)
C10A—C11A—C16A—C15A179.43 (13)C10B—C11B—C16B—C15B178.64 (13)
C12A—C11A—C16A—C15A0.9 (2)C12B—C11B—C16B—C15B0.1 (2)
C15A—C16A—C17A—C18A179.15 (13)C15B—C16B—C17B—C18B179.63 (14)
C11A—C16A—C17A—C18A0.0 (2)C11B—C16B—C17B—C18B0.4 (2)
C16A—C17A—C18A—C19A178.78 (14)C16B—C17B—C18B—C19B177.25 (14)
C16A—C17A—C18A—C23A1.3 (2)C16B—C17B—C18B—C23B1.2 (2)
C17A—C18A—C19A—C20A178.58 (15)C17B—C18B—C19B—C20B178.46 (14)
C23A—C18A—C19A—C20A1.3 (2)C23B—C18B—C19B—C20B0.0 (2)
C18A—C19A—C20A—C21A1.3 (3)C18B—C19B—C20B—C21B0.6 (2)
C19A—C20A—C21A—C22A1.7 (3)C19B—C20B—C21B—C22B0.5 (2)
C20A—C21A—C22A—C23A0.6 (2)C20B—C21B—C22B—C23B0.3 (2)
C11A—C10A—C23A—C22A176.64 (13)C11B—C10B—C23B—C18B0.6 (2)
C9A—C10A—C23A—C22A4.4 (2)C9B—C10B—C23B—C18B179.51 (13)
C11A—C10A—C23A—C18A2.1 (2)C11B—C10B—C23B—C22B175.76 (13)
C9A—C10A—C23A—C18A176.86 (13)C9B—C10B—C23B—C22B4.2 (2)
C21A—C22A—C23A—C10A178.13 (14)C17B—C18B—C23B—C10B1.1 (2)
C21A—C22A—C23A—C18A3.1 (2)C19B—C18B—C23B—C10B177.35 (13)
C17A—C18A—C23A—C10A2.4 (2)C17B—C18B—C23B—C22B177.69 (13)
C19A—C18A—C23A—C10A177.75 (13)C19B—C18B—C23B—C22B0.8 (2)
C17A—C18A—C23A—C22A176.46 (13)C21B—C22B—C23B—C10B177.36 (14)
C19A—C18A—C23A—C22A3.4 (2)C21B—C22B—C23B—C18B1.0 (2)
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x+1, y+1, z+1; (iii) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O2A0.841.832.5729 (15)146
O1B—H1B···O2B0.841.802.5452 (16)146
C14B—H14B···O1Biv0.952.603.537 (2)169
Symmetry code: (iv) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC23H16O2
Mr324.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)110
a, b, c (Å)14.0748 (5), 13.7362 (5), 16.9800 (8)
β (°) 101.487 (5)
V3)3217.1 (2)
Z8
Radiation typeCu Kα
µ (mm1)0.67
Crystal size (mm)0.46 × 0.35 × 0.16
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Ruby (Gemini Cu) detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.530, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
14048, 6371, 5277
Rint0.022
(sin θ/λ)max1)0.624
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.134, 1.06
No. of reflections6371
No. of parameters453
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.24

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O2A0.841.832.5729 (15)146
O1B—H1B···O2B0.841.802.5452 (16)146
C14B—H14B···O1Bi0.952.603.537 (2)169
Symmetry code: (i) x+1, y1/2, z+3/2.
 

Acknowledgements

VMK thanks P. A. College of Engineering for the research facilities. HSY thanks the UOM for sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

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First citationSuwunwong, T., Chantrapromma, S., Karalai, C., Pakdeevanich, P. & Fun, H.-K. (2009). Acta Cryst. E65, o420–o421.  Web of Science CSD CrossRef IUCr Journals
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