trans-5,6-Diphenyl-perhydro-pyran-2,4-dione.

In the title compound, C(17)H(14)O(3), the pyran ring adopts a boat conformation and the dihedral angle between the aromatic ring planes is 59.1 (1)°. In the crystal structure inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions link the mol-ecules.

Related literature

For general background, see: Yen & Chen (1995 ▶); Soler-Rivas et al. (2000 ▶). For related structures and biological activity, see: Brand-William et al. (1995 ▶); Sánchez-Moreno et al. (1998 ▶); Souza et al. (2004 ▶). For the synthesis, see: Souza (2008 ▶). For geometric analysis, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H14O3

M = 266.28

Monoclinic,

a = 8.9940 (2) Å

b = 8.2310 (4) Å

c = 18.9040 (8) Å

β = 101.412 (2)°

V = 1371.79 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.30 × 0.30 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

5298 measured reflections

3113 independent reflections

2459 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.131

S = 1.05

3113 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000087/bq2110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000087/bq2110Isup2.hkl

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

C17H14O3	F(000) = 560
Mr = 266.28	Dx = 1.289 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 2880 reflections
a = 8.9940 (2) Å	θ = 1.0–27.5°
b = 8.2310 (4) Å	µ = 0.09 mm−1
c = 18.9040 (8) Å	T = 295 K
β = 101.412 (2)°	Prism, yellow
V = 1371.79 (9) Å3	0.30 × 0.30 × 0.18 mm
Z = 4

Nonius KappaCCD diffractometer	2459 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.017
horizonally mounted graphite crystal	θmax = 27.5°, θmin = 2.3°
Detector resolution: 9 pixels mm-1	h = −11→11
CCD rotation images, thick slices scans	k = −9→10
5298 measured reflections	l = −24→24
3113 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.3831P] where P = (Fo2 + 2Fc2)/3
3113 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
C2	0.69397 (19)	−0.0595 (2)	0.63794 (8)	0.0521 (4)
C3	0.84834 (19)	0.0134 (2)	0.65634 (8)	0.0560 (4)
H3A	0.8717	0.0620	0.6131	0.067*
H3B	0.9211	−0.0730	0.6712	0.067*
C4	0.86937 (16)	0.1403 (2)	0.71484 (8)	0.0476 (4)
C5	0.76480 (14)	0.12492 (17)	0.76852 (7)	0.0383 (3)
H5	0.6771	0.1953	0.7515	0.046*
C6	0.70604 (15)	−0.05049 (17)	0.76642 (7)	0.0385 (3)
H6	0.7925	−0.1246	0.7790	0.046*
C7	0.83633 (14)	0.17992 (16)	0.84390 (7)	0.0385 (3)
C8	0.76586 (17)	0.2946 (2)	0.87924 (9)	0.0520 (4)
H8	0.6745	0.3402	0.8562	0.062*
C9	0.8303 (2)	0.3421 (2)	0.94867 (10)	0.0652 (5)
H9	0.7817	0.4189	0.9722	0.078*
C10	0.9657 (2)	0.2763 (2)	0.98306 (9)	0.0631 (5)
H10	1.0094	0.3097	1.0295	0.076*
C11	1.03660 (18)	0.1616 (2)	0.94891 (9)	0.0565 (4)
H11	1.1281	0.1166	0.9723	0.068*
C12	0.97190 (16)	0.11267 (19)	0.87959 (8)	0.0477 (4)
H12	1.0198	0.0340	0.8567	0.057*
C13	0.59831 (15)	−0.07985 (17)	0.81644 (7)	0.0412 (3)
C14	0.46566 (19)	0.0086 (2)	0.80971 (12)	0.0644 (5)
H14	0.4401	0.0834	0.7724	0.077*
C15	0.3711 (3)	−0.0137 (3)	0.85803 (16)	0.0935 (8)
H15	0.2827	0.0473	0.8535	0.112*
C16	0.4061 (3)	−0.1242 (4)	0.91217 (15)	0.1019 (10)
H16	0.3420	−0.1378	0.9447	0.122*
C17	0.5352 (3)	−0.2153 (4)	0.91893 (11)	0.0967 (9)
H17	0.5583	−0.2915	0.9558	0.116*
C18	0.6323 (2)	−0.1938 (2)	0.87041 (9)	0.0643 (5)
H18	0.7197	−0.2564	0.8746	0.077*
O1	0.62369 (12)	−0.08786 (13)	0.69346 (5)	0.0487 (3)
O2	0.96257 (15)	0.24604 (19)	0.71798 (7)	0.0767 (4)
O3	0.63076 (17)	−0.0935 (2)	0.57795 (6)	0.0792 (4)

	U11	U22	U33	U12	U13	U23
C2	0.0651 (10)	0.0484 (9)	0.0431 (8)	0.0015 (7)	0.0113 (7)	−0.0051 (7)
C3	0.0617 (9)	0.0655 (10)	0.0462 (8)	−0.0027 (8)	0.0239 (7)	−0.0015 (7)
C4	0.0423 (7)	0.0550 (9)	0.0467 (8)	−0.0069 (7)	0.0113 (6)	0.0061 (7)
C5	0.0347 (6)	0.0387 (7)	0.0422 (7)	−0.0028 (5)	0.0091 (5)	0.0005 (6)
C6	0.0368 (6)	0.0390 (7)	0.0393 (7)	−0.0005 (5)	0.0065 (5)	−0.0010 (5)
C7	0.0355 (6)	0.0375 (7)	0.0436 (7)	−0.0054 (5)	0.0105 (5)	−0.0013 (6)
C8	0.0456 (8)	0.0520 (9)	0.0578 (9)	0.0054 (7)	0.0089 (7)	−0.0089 (7)
C9	0.0683 (11)	0.0677 (11)	0.0606 (10)	0.0065 (9)	0.0158 (8)	−0.0212 (9)
C10	0.0674 (11)	0.0741 (12)	0.0456 (9)	−0.0053 (9)	0.0054 (7)	−0.0149 (8)
C11	0.0462 (8)	0.0640 (10)	0.0558 (9)	0.0005 (7)	0.0015 (7)	−0.0007 (8)
C12	0.0400 (7)	0.0506 (8)	0.0524 (8)	0.0012 (6)	0.0091 (6)	−0.0066 (7)
C13	0.0426 (7)	0.0381 (7)	0.0435 (7)	−0.0100 (5)	0.0100 (6)	−0.0046 (6)
C14	0.0544 (9)	0.0477 (9)	0.0998 (14)	−0.0010 (7)	0.0365 (9)	0.0020 (9)
C15	0.0823 (14)	0.0728 (14)	0.147 (2)	−0.0182 (11)	0.0759 (15)	−0.0221 (15)
C16	0.113 (2)	0.118 (2)	0.0933 (17)	−0.0592 (18)	0.0672 (16)	−0.0339 (16)
C17	0.1149 (19)	0.122 (2)	0.0517 (11)	−0.0542 (18)	0.0137 (12)	0.0191 (12)
C18	0.0620 (10)	0.0742 (12)	0.0529 (9)	−0.0146 (9)	0.0023 (8)	0.0170 (9)
O1	0.0522 (6)	0.0502 (6)	0.0433 (6)	−0.0104 (5)	0.0084 (4)	−0.0078 (5)
O2	0.0722 (8)	0.0922 (10)	0.0712 (8)	−0.0402 (7)	0.0275 (6)	−0.0053 (7)
O3	0.0974 (10)	0.0914 (10)	0.0454 (7)	−0.0122 (8)	0.0061 (6)	−0.0174 (7)

C2—O3	1.1971 (19)	C9—C10	1.374 (3)
C2—O1	1.3484 (19)	C9—H9	0.9300
C2—C3	1.489 (2)	C10—C11	1.370 (2)
C3—C4	1.506 (2)	C10—H10	0.9300
C3—H3A	0.9700	C11—C12	1.384 (2)
C3—H3B	0.9700	C11—H11	0.9300
C4—O2	1.2013 (19)	C12—H12	0.9300
C4—C5	1.5191 (19)	C13—C18	1.375 (2)
C5—C7	1.5122 (18)	C13—C14	1.382 (2)
C5—C6	1.5353 (19)	C14—C15	1.378 (3)
C5—H5	0.9800	C14—H14	0.9300
C6—O1	1.4633 (16)	C15—C16	1.358 (4)
C6—C13	1.5013 (18)	C15—H15	0.9300
C6—H6	0.9800	C16—C17	1.367 (4)
C7—C8	1.381 (2)	C16—H16	0.9300
C7—C12	1.387 (2)	C17—C18	1.398 (3)
C8—C9	1.382 (2)	C17—H17	0.9300
C8—H8	0.9300	C18—H18	0.9300
O3—C2—O1	119.27 (16)	C10—C9—H9	119.9
O3—C2—C3	124.18 (16)	C8—C9—H9	119.9
O1—C2—C3	116.55 (13)	C11—C10—C9	120.03 (16)
C2—C3—C4	115.28 (13)	C11—C10—H10	120.0
C2—C3—H3A	108.5	C9—C10—H10	120.0
C4—C3—H3A	108.5	C10—C11—C12	119.91 (15)
C2—C3—H3B	108.5	C10—C11—H11	120.0
C4—C3—H3B	108.5	C12—C11—H11	120.0
H3A—C3—H3B	107.5	C11—C12—C7	120.60 (14)
O2—C4—C3	121.58 (14)	C11—C12—H12	119.7
O2—C4—C5	123.07 (15)	C7—C12—H12	119.7
C3—C4—C5	115.35 (12)	C18—C13—C14	119.27 (15)
C7—C5—C4	113.59 (11)	C18—C13—C6	120.03 (14)
C7—C5—C6	112.70 (11)	C14—C13—C6	120.69 (14)
C4—C5—C6	108.47 (11)	C15—C14—C13	120.3 (2)
C7—C5—H5	107.2	C15—C14—H14	119.9
C4—C5—H5	107.2	C13—C14—H14	119.9
C6—C5—H5	107.2	C16—C15—C14	120.5 (2)
O1—C6—C13	106.88 (10)	C16—C15—H15	119.8
O1—C6—C5	109.24 (11)	C14—C15—H15	119.8
C13—C6—C5	113.39 (11)	C15—C16—C17	120.2 (2)
O1—C6—H6	109.1	C15—C16—H16	119.9
C13—C6—H6	109.1	C17—C16—H16	119.9
C5—C6—H6	109.1	C16—C17—C18	119.9 (2)
C8—C7—C12	118.76 (13)	C16—C17—H17	120.0
C8—C7—C5	120.68 (13)	C18—C17—H17	120.0
C12—C7—C5	120.54 (13)	C13—C18—C17	119.8 (2)
C7—C8—C9	120.43 (15)	C13—C18—H18	120.1
C7—C8—H8	119.8	C17—C18—H18	120.1
C9—C8—H8	119.8	C2—O1—C6	118.00 (11)
C10—C9—C8	120.25 (16)
O3—C2—C3—C4	141.51 (18)	C9—C10—C11—C12	0.3 (3)
O1—C2—C3—C4	−38.6 (2)	C10—C11—C12—C7	0.6 (3)
C2—C3—C4—O2	−153.41 (17)	C8—C7—C12—C11	−1.0 (2)
C2—C3—C4—C5	26.3 (2)	C5—C7—C12—C11	−179.25 (14)
O2—C4—C5—C7	−33.0 (2)	O1—C6—C13—C18	119.45 (14)
C3—C4—C5—C7	147.27 (13)	C5—C6—C13—C18	−120.13 (15)
O2—C4—C5—C6	−159.12 (16)	O1—C6—C13—C14	−61.63 (17)
C3—C4—C5—C6	21.12 (17)	C5—C6—C13—C14	58.80 (18)
C7—C5—C6—O1	173.61 (10)	C18—C13—C14—C15	2.1 (3)
C4—C5—C6—O1	−59.72 (13)	C6—C13—C14—C15	−176.85 (17)
C7—C5—C6—C13	54.54 (15)	C13—C14—C15—C16	−0.9 (3)
C4—C5—C6—C13	−178.80 (11)	C14—C15—C16—C17	−0.5 (4)
C4—C5—C7—C8	126.23 (15)	C15—C16—C17—C18	0.6 (4)
C6—C5—C7—C8	−109.89 (15)	C14—C13—C18—C17	−1.9 (3)
C4—C5—C7—C12	−55.59 (18)	C6—C13—C18—C17	176.99 (16)
C6—C5—C7—C12	68.29 (16)	C16—C17—C18—C13	0.6 (3)
C12—C7—C8—C9	0.5 (2)	O3—C2—O1—C6	177.79 (15)
C5—C7—C8—C9	178.72 (15)	C3—C2—O1—C6	−2.1 (2)
C7—C8—C9—C10	0.4 (3)	C13—C6—O1—C2	175.37 (12)
C8—C9—C10—C11	−0.9 (3)	C5—C6—O1—C2	52.33 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.98	2.44	3.380 (2)	161
C17—H17···O3ii	0.93	2.46	3.351 (3)	160
C3—H3B···Cg1i	0.97	2.98	3.681 (2)	131
C5—H5···Cg2iii	0.98	2.96	3.830 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.98	2.44	3.380 (2)	161
C17—H17⋯O3ii	0.93	2.46	3.351 (3)	160
C3—H3B⋯Cg1i	0.97	2.97	3.681 (2)	131
C5—H5⋯Cg2iii	0.98	2.96	3.830 (2)	149

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C7–C12 and C13–C18 rings, respectively.