Crystal structure and conformational analysis of 2-hy­droxy-3-(2-methyl­prop-1-en-1-yl)naphthalene-1,4-dione

In the structure of the naphtho­quinone derivative 2-hy­droxy-3-(2-methyl­prop-1-en-1-yl)naphthalene-1,4-dione, the mol­ecules form a centrosymmetric cyclic dimer through inter­molecular O—H...O hydrogen bonds which, together with inter­molecular C—H...O hydrogen bonds and weak π–π ring inter­actions, give rise to an overall two-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.061
• wR factor = 0.191
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.138 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          8 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found in the CIF      Please Do !
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H12A   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H12B   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H12C   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H12D   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H12E   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H12F   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H22A   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H22B   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H22C   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H22D   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H22E   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H22F   is Constrained at        0.5 Check
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C1     -C8A           1.45 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  19 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
  14 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

S1. Chemical context

Naphtho­quinone compounds exhibit several biological activities, being utilized for the treatment of parasitic diseases (Salas et al., 2008) some types of cancer (Tonholo et al., 1998) and cardiovascular disease (Silva & Torres, 2013). The compound in this study, 2-hy­droxy-3-(2-metilprop-1-enol)naphthalene-1,4-dione, C₁₄H₁₂O₃, is a naphtho­quinone derivative and the structure is reported herein.

S2. Structural commentary

The molecular structure of the title compound is shown in Fig. 1. In this structure the side chain is rotated out of the plane of the naphthalene­dione ring, with torsion angles C2—C3—C9—C10, C3—C9—C10—C12 and C3—C9—C10—C22 of 50.7 (3), −176.6 (2) and 4.9 (4)°, respectively. Present also in the molecule is an intra­molecular methyl C22···O3 [2.959 (3) Å] and a short O3···O1 contact [2.665 (2) Å]. When compared with other analogous structures in the literature, e.g. 2-chloro-3-(4-chloro­benzamido)-1,4-naphtho­quinone (Brandy et al., 2009), it is observed that in the title compound has similar conformational features with respect to the side chain, which lies outside of the naphtho­quinone plane.

S3. Supra­molecular features

In the crystal, the molecules are connected by classic inter­molecular O3—H···O1ⁱ hydrogen bonds (Table 1), forming a centrosymmetric cyclic dimer [graph set R₂²(10)] (Bernstein et al., 1995) (Fig. 2a). Also present in the structure is a weak inter­molecular C7—H···O2ⁱⁱ hydrogen bond [3.339 (3) °], linking the dimers and a weak π–π ring inter­action between the benzene and quinone ring moieties of the parent ring system [ring centroid separation Cg···Cgⁱⁱⁱ = 3.7862 (13) Å] [symmetry code (iii): x + 1, y, z], giving layers down the a-axis direction (Figs. 2b and 3).

S4. Database survey

A search of the Cambridge Structural Database (Groom & Allen, 2014) revealed the presence of 40 structures containing the 2-hy­droxy­naphthalene-1,4-dione core moiety. There were 787 structures which possess the the naphtalene-1,4-dione moiety. There are similar structures to the title compound, its variants being dependant on the oxidant used in the syntheses.

S5. Synthesis and crystallization

The compound was obtained through to the lapachol oxidation product as can be seen in Scheme 2 below (Hooker, 1936). The sample was subjected to an ethyl acetate solution at 301 K for crystallization.

S6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The O3-bound H atom was located in a difference Fourier map and was freely refined. The remaining H atoms were positioned geometrically with aromatic C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C). Rotational disorder was identified in the hydrogen atoms of the methyl carbon atoms C12 and C22 and these were included in the refinement over six equivalent 60° sites with 50% occupation, with C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C).

Structure description

Naphtho­quinone compounds exhibit several biological activities, being utilized for the treatment of parasitic diseases (Salas et al., 2008) some types of cancer (Tonholo et al., 1998) and cardiovascular disease (Silva & Torres, 2013). The compound in this study, 2-hy­droxy-3-(2-metilprop-1-enol)naphthalene-1,4-dione, C₁₄H₁₂O₃, is a naphtho­quinone derivative and the structure is reported herein.

The molecular structure of the title compound is shown in Fig. 1. In this structure the side chain is rotated out of the plane of the naphthalene­dione ring, with torsion angles C2—C3—C9—C10, C3—C9—C10—C12 and C3—C9—C10—C22 of 50.7 (3), −176.6 (2) and 4.9 (4)°, respectively. Present also in the molecule is an intra­molecular methyl C22···O3 [2.959 (3) Å] and a short O3···O1 contact [2.665 (2) Å]. When compared with other analogous structures in the literature, e.g. 2-chloro-3-(4-chloro­benzamido)-1,4-naphtho­quinone (Brandy et al., 2009), it is observed that in the title compound has similar conformational features with respect to the side chain, which lies outside of the naphtho­quinone plane.

In the crystal, the molecules are connected by classic inter­molecular O3—H···O1ⁱ hydrogen bonds (Table 1), forming a centrosymmetric cyclic dimer [graph set R₂²(10)] (Bernstein et al., 1995) (Fig. 2a). Also present in the structure is a weak inter­molecular C7—H···O2ⁱⁱ hydrogen bond [3.339 (3) °], linking the dimers and a weak π–π ring inter­action between the benzene and quinone ring moieties of the parent ring system [ring centroid separation Cg···Cgⁱⁱⁱ = 3.7862 (13) Å] [symmetry code (iii): x + 1, y, z], giving layers down the a-axis direction (Figs. 2b and 3).

A search of the Cambridge Structural Database (Groom & Allen, 2014) revealed the presence of 40 structures containing the 2-hy­droxy­naphthalene-1,4-dione core moiety. There were 787 structures which possess the the naphtalene-1,4-dione moiety. There are similar structures to the title compound, its variants being dependant on the oxidant used in the syntheses.

Synthesis and crystallization

The compound was obtained through to the lapachol oxidation product as can be seen in Scheme 2 below (Hooker, 1936). The sample was subjected to an ethyl acetate solution at 301 K for crystallization.

Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 2. The O3-bound H atom was located in a difference Fourier map and was freely refined. The remaining H atoms were positioned geometrically with aromatic C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C). Rotational disorder was identified in the hydrogen atoms of the methyl carbon atoms C12 and C22 and these were included in the refinement over six equivalent 60° sites with 50% occupation, with C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C).

Computing details

Data collection: COLLECT (Enraf–Nonius, 2001); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Figures

	Fig. 1. Molecular conformation and atom-numbering scheme, with non-H atoms drawn at the 50% probability level. The H atoms of the rotationally disordered methyl groups are shown as six equivalent half-occupancy sites.
	Fig. 2. The centrosymmetric dimers formed from the O3—H···O1^i hydrogen bonds, viewed (a) along a and (b) along b. For symmetry code (i), see Table 1.
	Fig. 3. The crystal packing in the unit cell, showing intra- and intermolecular interactions as dashed lines.

2-Hydroxy-3-(2-methylprop-1-en-1-yl)naphthalene-1,4-dione

Crystal data

C14H12O3	F(000) = 480
Mr = 228.24	Dx = 1.342 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2659 reflections
a = 4.3564 (2) Å	θ = 1.0–27.5°
b = 16.4069 (8) Å	µ = 0.09 mm^−1
c = 15.8598 (7) Å	T = 293 K
β = 94.793 (2)°	Block, red
V = 1129.62 (9) Å^3	0.14 × 0.11 × 0.10 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	1802 reflections with I > 2σ(I)
Radiation source: Enraf-Nonius FR590	Rint = 0.041
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
Detector resolution: 9 pixels mm^-1	h = −5→5
CCD rotation images, thick slices scans	k = −19→21
4661 measured reflections	l = −20→20
2585 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.191	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0946P)^2 + 0.4119P] where P = (Fo^2 + 2Fc^2)/3
2585 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O3	0.3690 (4)	0.37038 (10)	0.48362 (10)	0.0407 (4)
O1	0.2205 (4)	0.52143 (9)	0.43377 (9)	0.0404 (4)
O2	−0.3406 (4)	0.27382 (9)	0.26721 (10)	0.0481 (5)
C10	0.0940 (5)	0.19603 (13)	0.47932 (13)	0.0395 (5)
C9	0.0749 (5)	0.23006 (12)	0.40272 (13)	0.0386 (5)
H9	0.1126	0.1961	0.3578	0.046*
H1O3	0.448 (7)	0.424 (2)	0.5005 (19)	0.073 (9)*
C4A	−0.3114 (5)	0.41650 (12)	0.28476 (13)	0.0349 (5)
C8A	−0.1689 (5)	0.48205 (13)	0.32860 (13)	0.0348 (5)
C2	0.1441 (5)	0.38047 (12)	0.42115 (13)	0.0351 (5)
C1	0.0733 (5)	0.46622 (12)	0.39675 (13)	0.0350 (5)
C5	−0.5333 (5)	0.43122 (14)	0.21845 (13)	0.0400 (5)
H5	−0.6268	0.3879	0.1885	0.048*
C3	0.0007 (5)	0.31557 (12)	0.38155 (12)	0.0358 (5)
C4	−0.2235 (5)	0.33077 (13)	0.30859 (13)	0.0369 (5)
C6	−0.6151 (5)	0.51093 (14)	0.19709 (14)	0.0426 (5)
H6	−0.7628	0.5207	0.1524	0.051*
C8	−0.2532 (5)	0.56203 (13)	0.30691 (14)	0.0386 (5)
H8	−0.1584	0.6056	0.3362	0.046*
C7	−0.4789 (5)	0.57607 (13)	0.24159 (14)	0.0413 (5)
H7	−0.5389	0.6291	0.2277	0.05*
C12	0.1899 (6)	0.10858 (13)	0.49043 (15)	0.0475 (6)
H12A	0.1919	0.0939	0.5491	0.071*	0.5
H12B	0.3923	0.1015	0.4718	0.071*	0.5
H12C	0.0468	0.0744	0.4575	0.071*	0.5
H12D	0.2288	0.086	0.4365	0.071*	0.5
H12E	0.0283	0.0784	0.5138	0.071*	0.5
H12F	0.3738	0.1055	0.5281	0.071*	0.5
C22	0.0189 (6)	0.23815 (14)	0.55869 (14)	0.0452 (6)
H22A	0.0507	0.2013	0.6056	0.068*	0.5
H22B	−0.1923	0.2554	0.553	0.068*	0.5
H22C	0.1503	0.2848	0.5684	0.068*	0.5
H22D	−0.0449	0.2931	0.5457	0.068*	0.5
H22E	0.1981	0.2389	0.5983	0.068*	0.5
H22F	−0.1445	0.2095	0.583	0.068*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0435 (9)	0.0323 (8)	0.0450 (9)	−0.0013 (6)	−0.0051 (6)	−0.0002 (7)
O1	0.0456 (9)	0.0318 (8)	0.0431 (8)	−0.0041 (6)	−0.0005 (6)	−0.0022 (6)
O2	0.0651 (11)	0.0308 (8)	0.0460 (9)	−0.0033 (7)	−0.0096 (7)	−0.0026 (7)
C10	0.0438 (12)	0.0302 (10)	0.0439 (12)	−0.0025 (8)	−0.0013 (9)	−0.0004 (9)
C9	0.0462 (12)	0.0282 (10)	0.0409 (11)	0.0009 (9)	0.0011 (9)	−0.0027 (9)
C4A	0.0422 (11)	0.0292 (10)	0.0340 (10)	−0.0011 (8)	0.0061 (8)	0.0012 (8)
C8A	0.0398 (11)	0.0305 (11)	0.0346 (10)	−0.0016 (8)	0.0057 (8)	−0.0001 (8)
C2	0.0384 (11)	0.0314 (11)	0.0355 (10)	0.0003 (8)	0.0035 (8)	0.0009 (8)
C1	0.0398 (11)	0.0288 (10)	0.0367 (10)	−0.0019 (8)	0.0055 (8)	−0.0034 (8)
C5	0.0486 (13)	0.0343 (11)	0.0368 (11)	−0.0025 (9)	0.0015 (9)	−0.0004 (9)
C3	0.0431 (11)	0.0292 (10)	0.0355 (10)	−0.0006 (8)	0.0064 (8)	−0.0006 (8)
C4	0.0453 (12)	0.0299 (10)	0.0357 (11)	−0.0025 (9)	0.0040 (9)	−0.0011 (8)
C6	0.0500 (13)	0.0383 (12)	0.0391 (11)	0.0013 (9)	0.0003 (9)	0.0039 (9)
C8	0.0460 (12)	0.0293 (10)	0.0410 (11)	−0.0005 (8)	0.0062 (9)	−0.0002 (8)
C7	0.0493 (12)	0.0312 (11)	0.0436 (11)	0.0027 (9)	0.0060 (9)	0.0055 (9)
C12	0.0651 (15)	0.0315 (11)	0.0447 (12)	0.0020 (10)	−0.0024 (10)	0.0011 (9)
C22	0.0587 (14)	0.0346 (11)	0.0420 (12)	0.0006 (10)	0.0033 (10)	0.0011 (9)

Geometric parameters (Å, º)

O3—C2	1.344 (3)	C3—C4	1.472 (3)
O3—H1O3	0.97 (4)	C6—C7	1.387 (3)
O1—C1	1.230 (2)	C6—H6	0.93
O2—C4	1.228 (2)	C8—C7	1.387 (3)
C10—C9	1.333 (3)	C8—H8	0.93
C10—C22	1.496 (3)	C7—H7	0.93
C10—C12	1.501 (3)	C12—H12A	0.96
C9—C3	1.472 (3)	C12—H12B	0.96
C9—H9	0.93	C12—H12C	0.96
C4A—C5	1.389 (3)	C12—H12D	0.96
C4A—C8A	1.398 (3)	C12—H12E	0.96
C4A—C4	1.498 (3)	C12—H12F	0.96
C8A—C8	1.398 (3)	C22—H22A	0.96
C8A—C1	1.469 (3)	C22—H22B	0.96
C2—C3	1.361 (3)	C22—H22C	0.96
C2—C1	1.485 (3)	C22—H22D	0.96
C5—C6	1.390 (3)	C22—H22E	0.96
C5—H5	0.93	C22—H22F	0.96
C2—O3—H1O3	108.3 (18)	C10—C12—H12C	109.5
C9—C10—C22	124.9 (2)	H12A—C12—H12C	109.5
C9—C10—C12	120.2 (2)	H12B—C12—H12C	109.5
C22—C10—C12	114.91 (19)	C10—C12—H12D	109.5
C10—C9—C3	127.1 (2)	H12A—C12—H12D	141.1
C10—C9—H9	116.5	H12B—C12—H12D	56.3
C3—C9—H9	116.5	H12C—C12—H12D	56.3
C5—C4A—C8A	119.67 (19)	C10—C12—H12E	109.5
C5—C4A—C4	120.09 (19)	H12A—C12—H12E	56.3
C8A—C4A—C4	120.23 (18)	H12B—C12—H12E	141.1
C4A—C8A—C8	120.21 (19)	H12C—C12—H12E	56.3
C4A—C8A—C1	119.46 (19)	H12D—C12—H12E	109.5
C8—C8A—C1	120.32 (19)	C10—C12—H12F	109.5
O3—C2—C3	121.45 (19)	H12A—C12—H12F	56.3
O3—C2—C1	115.56 (18)	H12B—C12—H12F	56.3
C3—C2—C1	122.95 (19)	H12C—C12—H12F	141.1
O1—C1—C8A	122.31 (19)	H12D—C12—H12F	109.5
O1—C1—C2	119.00 (18)	H12E—C12—H12F	109.5
C8A—C1—C2	118.68 (18)	C10—C22—H22A	109.5
C4A—C5—C6	119.8 (2)	C10—C22—H22B	109.5
C4A—C5—H5	120.1	H22A—C22—H22B	109.5
C6—C5—H5	120.1	C10—C22—H22C	109.5
C2—C3—C4	118.61 (19)	H22A—C22—H22C	109.5
C2—C3—C9	123.83 (19)	H22B—C22—H22C	109.5
C4—C3—C9	117.35 (18)	C10—C22—H22D	109.5
O2—C4—C3	120.66 (19)	H22A—C22—H22D	141.1
O2—C4—C4A	119.58 (18)	H22B—C22—H22D	56.3
C3—C4—C4A	119.76 (18)	H22C—C22—H22D	56.3
C7—C6—C5	120.7 (2)	C10—C22—H22E	109.5
C7—C6—H6	119.6	H22A—C22—H22E	56.3
C5—C6—H6	119.6	H22B—C22—H22E	141.1
C7—C8—C8A	119.7 (2)	H22C—C22—H22E	56.3
C7—C8—H8	120.2	H22D—C22—H22E	109.5
C8A—C8—H8	120.2	C10—C22—H22F	109.5
C6—C7—C8	119.9 (2)	H22A—C22—H22F	56.3
C6—C7—H7	120	H22B—C22—H22F	56.3
C8—C7—H7	120	H22C—C22—H22F	141.1
C10—C12—H12A	109.5	H22D—C22—H22F	109.5
C10—C12—H12B	109.5	H22E—C22—H22F	109.5
H12A—C12—H12B	109.5
O1—C1—C2—O3	0.2 (3)	O2—C4—C4A—C5	2.6 (3)
O1—C1—C2—C3	−177.5 (2)	O2—C4—C4A—C8A	−176.8 (2)
C8A—C1—C2—O3	179.69 (19)	C3—C4—C4A—C5	−177.0 (2)
C8A—C1—C2—C3	2.0 (3)	C3—C4—C4A—C8A	3.5 (3)
O1—C1—C8A—C4A	175.2 (2)	C4—C4A—C5—C6	179.6 (2)
O1—C1—C8A—C8	−3.9 (3)	C8A—C4A—C5—C6	−1.0 (3)
C2—C1—C8A—C4A	−4.3 (3)	C4—C4A—C8A—C1	1.6 (3)
C2—C1—C8A—C8	176.6 (2)	C4—C4A—C8A—C8	−179.4 (2)
O3—C2—C3—C4	−174.50 (19)	C5—C4A—C8A—C1	−177.9 (2)
O3—C2—C3—C9	0.2 (3)	C5—C4A—C8A—C8	1.2 (3)
C1—C2—C3—C4	3.1 (3)	C4A—C5—C6—C7	−0.4 (3)
C1—C2—C3—C9	177.8 (2)	C5—C6—C7—C8	1.5 (3)
C2—C3—C4—O2	174.5 (2)	C6—C7—C8—C8A	−1.3 (3)
C2—C3—C4—C4A	−5.9 (3)	C7—C8—C8A—C1	179.0 (2)
C9—C3—C4—O2	−0.5 (3)	C7—C8—C8A—C4A	−0.1 (3)
C9—C3—C4—C4A	179.15 (19)	C3—C9—C10—C12	−176.6 (2)
C2—C3—C9—C10	50.7 (3)	C3—C9—C10—C22	4.9 (4)
C4—C3—C9—C10	−134.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O1^i	0.97 (3)	1.93 (3)	2.770 (2)	143 (3)
C7—H7···O2^ii	0.93	2.43	3.339 (3)	164
C22—H22C···O3	0.96	2.21	2.959 (3)	134

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x−1, y+1/2, −z+1/2.