Phenyl 3-phenyl­oxiran-2-yl ketone

In the mol­ecule of the title compound, C₁₅H₁₂O₂, all three rings are, of course, planar. The oxirane ring makes dihedral angles of 82.12 (2) and 70.37 (2)° with the phenyl rings. The phenyl rings make a dihedral angle of 78.17 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.116
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick,1997a); program(s) used to refine structure: SHELXL97 (Sheldrick,1997a); molecular graphics: SHELXTL (Sheldrick,1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)..

phenyl 3-phenyloxiran-2-yl ketone

Crystal data

C15H12O2	Dx = 1.284 Mg m^−3
Mr = 224.25	Melting point: 81(2) K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2.55 reflections
a = 10.4254 (9) Å	θ = 28.3–2883°
b = 7.9957 (7) Å	µ = 0.08 mm^−1
c = 27.826 (2) Å	T = 294 K
V = 2319.5 (3) Å^3	Block, colourless
Z = 8	0.28 × 0.25 × 0.20 mm
F(000) = 944

Data collection

Bruker SMART CCD area-detector diffractometer	2773 independent reflections
Radiation source: fine-focus sealed tube	1449 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω and φ scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→6
Tmin = 0.914, Tmax = 0.980	k = −9→10
12686 measured reflections	l = −36→36

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0395P)^2 + 0.4748P] where P = (Fo^2 + 2Fc^2)/3
2773 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0277 (2)	0.4168 (2)	0.33064 (5)	0.0566 (5)
C2	0.0944 (2)	0.5525 (2)	0.31339 (6)	0.0712 (6)
H2A	0.1825	0.5595	0.3181	0.085*
C3	0.0308 (3)	0.6786 (3)	0.28907 (7)	0.0900 (7)
H3A	0.0762	0.7705	0.2777	0.108*
C4	−0.0988 (3)	0.6685 (3)	0.28164 (7)	0.0899 (7)
H4A	−0.1409	0.7526	0.2648	0.108*
C5	−0.1663 (2)	0.5351 (3)	0.29898 (7)	0.0822 (6)
H5A	−0.2545	0.5293	0.2943	0.099*
C6	−0.1038 (2)	0.4091 (2)	0.32336 (6)	0.0678 (5)
H6A	−0.1501	0.3183	0.3350	0.081*
C7	0.09909 (19)	0.2807 (2)	0.35524 (6)	0.0600 (5)
H7A	0.1926	0.2930	0.3550	0.072*
C8	0.04748 (19)	0.1850 (2)	0.39579 (6)	0.0628 (5)
H8A	−0.0377	0.2170	0.4075	0.075*
C9	0.13880 (19)	0.1115 (2)	0.43189 (6)	0.0567 (4)
C10	0.11985 (16)	0.14930 (18)	0.48358 (6)	0.0479 (4)
C11	0.19709 (17)	0.0685 (2)	0.51686 (6)	0.0566 (4)
H11A	0.2589	−0.0070	0.5063	0.068*
C12	0.18352 (19)	0.0985 (2)	0.56510 (6)	0.0662 (5)
H12A	0.2362	0.0438	0.5870	0.079*
C13	0.0923 (2)	0.2091 (2)	0.58108 (7)	0.0698 (5)
H13A	0.0831	0.2290	0.6138	0.084*
C14	0.01464 (19)	0.2902 (2)	0.54884 (7)	0.0691 (5)
H14A	−0.0471	0.3652	0.5597	0.083*
C15	0.02827 (17)	0.2607 (2)	0.50035 (7)	0.0593 (4)
H15A	−0.0245	0.3160	0.4786	0.071*
O1	0.05404 (15)	0.11468 (15)	0.34901 (4)	0.0863 (5)
O2	0.22614 (14)	0.02349 (17)	0.41818 (4)	0.0786 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0746 (13)	0.0585 (10)	0.0368 (8)	−0.0031 (10)	0.0036 (9)	−0.0062 (7)
C2	0.0861 (15)	0.0734 (13)	0.0542 (10)	−0.0084 (12)	0.0107 (10)	0.0061 (10)
C3	0.128 (2)	0.0775 (15)	0.0645 (13)	−0.0059 (15)	0.0162 (14)	0.0192 (11)
C4	0.125 (2)	0.0910 (17)	0.0538 (12)	0.0268 (16)	−0.0009 (14)	0.0091 (11)
C5	0.0909 (17)	0.0967 (16)	0.0589 (12)	0.0143 (14)	−0.0111 (12)	−0.0080 (12)
C6	0.0815 (15)	0.0706 (12)	0.0513 (10)	−0.0054 (11)	−0.0016 (10)	−0.0061 (9)
C7	0.0744 (12)	0.0562 (10)	0.0493 (9)	−0.0067 (10)	0.0051 (9)	−0.0053 (8)
C8	0.0703 (13)	0.0656 (11)	0.0526 (10)	−0.0106 (10)	−0.0033 (9)	0.0018 (9)
C9	0.0593 (11)	0.0518 (10)	0.0591 (10)	−0.0090 (9)	0.0008 (9)	0.0022 (8)
C10	0.0468 (10)	0.0433 (8)	0.0536 (9)	−0.0070 (8)	−0.0002 (8)	0.0044 (7)
C11	0.0567 (11)	0.0519 (10)	0.0611 (10)	0.0022 (9)	−0.0026 (9)	0.0009 (8)
C12	0.0740 (13)	0.0666 (11)	0.0581 (11)	−0.0041 (11)	−0.0092 (10)	0.0070 (9)
C13	0.0806 (14)	0.0746 (13)	0.0541 (10)	−0.0159 (12)	0.0075 (11)	−0.0072 (10)
C14	0.0642 (12)	0.0671 (12)	0.0762 (13)	0.0010 (10)	0.0135 (11)	−0.0107 (10)
C15	0.0547 (10)	0.0552 (10)	0.0681 (11)	0.0027 (9)	−0.0030 (9)	0.0038 (8)
O1	0.1374 (14)	0.0602 (8)	0.0613 (8)	−0.0149 (8)	−0.0213 (8)	−0.0065 (6)
O2	0.0801 (10)	0.0880 (9)	0.0675 (8)	0.0143 (8)	0.0092 (7)	−0.0074 (7)

Geometric parameters (Å, º)

C1—C2	1.375 (2)	C8—C9	1.503 (2)
C1—C6	1.387 (3)	C8—H8A	0.9800
C1—C7	1.486 (2)	C9—O2	1.213 (2)
C2—C3	1.384 (3)	C9—C10	1.483 (2)
C2—H2A	0.9300	C10—C15	1.386 (2)
C3—C4	1.369 (3)	C10—C11	1.387 (2)
C3—H3A	0.9300	C11—C12	1.371 (2)
C4—C5	1.366 (3)	C11—H11A	0.9300
C4—H4A	0.9300	C12—C13	1.373 (2)
C5—C6	1.379 (3)	C12—H12A	0.9300
C5—H5A	0.9300	C13—C14	1.372 (3)
C6—H6A	0.9300	C13—H13A	0.9300
C7—O1	1.419 (2)	C14—C15	1.377 (3)
C7—C8	1.466 (2)	C14—H14A	0.9300
C7—H7A	0.9800	C15—H15A	0.9300
C8—O1	1.420 (2)
C2—C1—C6	118.94 (18)	C7—C8—C9	119.06 (17)
C2—C1—C7	119.06 (19)	O1—C8—H8A	116.9
C6—C1—C7	121.98 (17)	C7—C8—H8A	116.9
C1—C2—C3	120.2 (2)	C9—C8—H8A	116.9
C1—C2—H2A	119.9	O2—C9—C10	121.55 (16)
C3—C2—H2A	119.9	O2—C9—C8	119.49 (16)
C4—C3—C2	120.3 (2)	C10—C9—C8	118.96 (16)
C4—C3—H3A	119.9	C15—C10—C11	118.33 (16)
C2—C3—H3A	119.9	C15—C10—C9	123.29 (16)
C5—C4—C3	120.1 (2)	C11—C10—C9	118.38 (15)
C5—C4—H4A	120.0	C12—C11—C10	120.81 (17)
C3—C4—H4A	120.0	C12—C11—H11A	119.6
C4—C5—C6	120.1 (2)	C10—C11—H11A	119.6
C4—C5—H5A	120.0	C11—C12—C13	120.09 (17)
C6—C5—H5A	120.0	C11—C12—H12A	120.0
C5—C6—C1	120.4 (2)	C13—C12—H12A	120.0
C5—C6—H6A	119.8	C14—C13—C12	120.12 (18)
C1—C6—H6A	119.8	C14—C13—H13A	119.9
O1—C7—C8	58.93 (11)	C12—C13—H13A	119.9
O1—C7—C1	117.60 (16)	C13—C14—C15	119.92 (18)
C8—C7—C1	123.61 (17)	C13—C14—H14A	120.0
O1—C7—H7A	115.0	C15—C14—H14A	120.0
C8—C7—H7A	115.0	C14—C15—C10	120.73 (17)
C1—C7—H7A	115.0	C14—C15—H15A	119.6
O1—C8—C7	58.88 (11)	C10—C15—H15A	119.6
O1—C8—C9	115.31 (16)	C7—O1—C8	62.19 (10)
C6—C1—C2—C3	−0.2 (3)	O1—C8—C9—C10	−166.61 (14)
C7—C1—C2—C3	178.08 (16)	C7—C8—C9—C10	126.42 (17)
C1—C2—C3—C4	−0.6 (3)	O2—C9—C10—C15	174.22 (16)
C2—C3—C4—C5	1.1 (3)	C8—C9—C10—C15	−5.6 (2)
C3—C4—C5—C6	−1.0 (3)	O2—C9—C10—C11	−6.2 (2)
C4—C5—C6—C1	0.2 (3)	C8—C9—C10—C11	174.02 (14)
C2—C1—C6—C5	0.3 (3)	C15—C10—C11—C12	−0.2 (2)
C7—C1—C6—C5	−177.85 (16)	C9—C10—C11—C12	−179.89 (16)
C2—C1—C7—O1	−145.44 (16)	C10—C11—C12—C13	0.3 (3)
C6—C1—C7—O1	32.8 (2)	C11—C12—C13—C14	−0.2 (3)
C2—C1—C7—C8	145.16 (17)	C12—C13—C14—C15	0.0 (3)
C6—C1—C7—C8	−36.6 (2)	C13—C14—C15—C10	0.0 (3)
C1—C7—C8—O1	104.42 (19)	C11—C10—C15—C14	0.1 (2)
O1—C7—C8—C9	103.64 (19)	C9—C10—C15—C14	179.70 (16)
C1—C7—C8—C9	−151.94 (17)	C1—C7—O1—C8	−114.47 (18)
O1—C8—C9—O2	13.6 (2)	C9—C8—O1—C7	−110.00 (18)
C7—C8—C9—O2	−53.4 (2)