2-Benzyl-1,3-diphenyl­propane-1,3-dione

The mol­ecule of 2-benzyl-1,3-diphenyl­propane-1,3-dione, C₂₂H₁₈O₂, being a diketo tautomer, shows different stereochemistry from that of the closed-ring cis-ketoenol tautomer of the parent 1,3-diphenyl­propane-1,3-dione. The mol­ecular packing involves C—H...O and π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.152
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       0.91 mm

Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10    ..  O2      ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21    ..  O1      ..       2.74 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O1      ..       2.72 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 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
   0 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997), Mercury (Version 1.2.1; Bruno et al., 2002) RasTop (Valadon, 2004) and POV-RAY (Version 3.6; Persistence of Vision, 2004); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-benzyl-1,3-diphenylpropane-1,3-dione

Crystal data

C22H18O2	F(000) = 664
Mr = 314.36	Dx = 1.221 Mg m^−3
Monoclinic, P21/n	Melting point: 373 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.2935 (6) Å	Cell parameters from 44 reflections
b = 10.9060 (6) Å	θ = 10.0–16.6°
c = 15.4090 (7) Å	µ = 0.08 mm^−1
β = 98.562 (4)°	T = 298 K
V = 1710.55 (16) Å^3	Prismatic, colourless
Z = 4	0.91 × 0.80 × 0.60 mm

Data collection

Philips PW1100 diffractometer	Rint = 0.065
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 2.2°
Planar graphite monochromator	h = −13→13
ω scans	k = 0→13
3866 measured reflections	l = 0→19
3733 independent reflections	3 standard reflections every 60 min
2731 reflections with I > 2σ(I)	intensity decay: 2.8%

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.079P)^2 + 0.4571P] where P = (Fo^2 + 2Fc^2)/3
3733 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.17 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
O1	0.51686 (12)	0.52700 (13)	0.20738 (9)	0.0532 (3)
O2	0.23360 (13)	0.61609 (12)	0.22690 (11)	0.0627 (4)
C1	0.44644 (15)	0.46101 (15)	0.24339 (11)	0.0375 (4)
C2	0.31423 (14)	0.41891 (15)	0.19467 (10)	0.0358 (3)
H2	0.2932	0.3378	0.2161	0.043*
C3	0.20654 (16)	0.50947 (15)	0.20941 (11)	0.0399 (4)
C4	0.31760 (16)	0.41232 (16)	0.09528 (11)	0.0398 (4)
H4A	0.2305	0.3911	0.0660	0.048*
H4B	0.3386	0.4931	0.0749	0.048*
C5	0.41508 (15)	0.32107 (15)	0.06818 (10)	0.0379 (4)
C6	0.46244 (18)	0.33827 (17)	−0.01083 (12)	0.0467 (4)
H6	0.4364	0.4071	−0.0447	0.056*
C7	0.5473 (2)	0.2552 (2)	−0.03998 (14)	0.0597 (5)
H7	0.5774	0.2680	−0.0933	0.072*
C8	0.5878 (2)	0.1531 (2)	0.00980 (16)	0.0632 (6)
H8	0.6453	0.0972	−0.0096	0.076*
C9	0.5425 (2)	0.13489 (19)	0.08820 (15)	0.0578 (5)
H9	0.5695	0.0663	0.1220	0.069*
C10	0.45668 (17)	0.21813 (16)	0.11732 (12)	0.0468 (4)
H10	0.4267	0.2047	0.1705	0.056*
C11	0.48892 (16)	0.41663 (15)	0.33488 (11)	0.0407 (4)
C12	0.4019 (2)	0.36984 (18)	0.38672 (12)	0.0520 (5)
H12	0.3129	0.3649	0.3648	0.062*
C13	0.4474 (3)	0.3301 (2)	0.47178 (14)	0.0666 (6)
H13	0.3887	0.3000	0.5070	0.080*
C14	0.5793 (3)	0.3354 (2)	0.50323 (14)	0.0694 (6)
H14	0.6095	0.3090	0.5600	0.083*
C15	0.6673 (2)	0.3795 (2)	0.45173 (15)	0.0669 (6)
H15	0.7567	0.3811	0.4733	0.080*
C16	0.62267 (19)	0.42125 (18)	0.36806 (13)	0.0526 (5)
H16	0.6818	0.4526	0.3337	0.063*
C17	0.06737 (15)	0.46646 (15)	0.19615 (11)	0.0386 (4)
C18	−0.03107 (18)	0.55264 (19)	0.17094 (13)	0.0534 (5)
H18	−0.0089	0.6341	0.1630	0.064*
C19	−0.1609 (2)	0.5175 (2)	0.15776 (16)	0.0662 (6)
H19	−0.2260	0.5754	0.1408	0.079*
C20	−0.19506 (19)	0.3977 (2)	0.16944 (16)	0.0647 (6)
H20	−0.2830	0.3745	0.1594	0.078*
C21	−0.09947 (19)	0.3115 (2)	0.19601 (15)	0.0605 (5)
H21	−0.1229	0.2308	0.2053	0.073*
C22	0.03220 (17)	0.34556 (17)	0.20886 (13)	0.0475 (4)
H22	0.0968	0.2872	0.2260	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0429 (7)	0.0602 (8)	0.0558 (8)	−0.0124 (6)	0.0051 (6)	0.0079 (6)
O2	0.0455 (7)	0.0407 (7)	0.1026 (12)	−0.0016 (6)	0.0127 (7)	−0.0171 (7)
C1	0.0332 (8)	0.0372 (8)	0.0425 (8)	0.0001 (6)	0.0072 (6)	−0.0013 (7)
C2	0.0308 (7)	0.0360 (8)	0.0409 (8)	0.0002 (6)	0.0060 (6)	−0.0004 (6)
C3	0.0370 (8)	0.0371 (9)	0.0462 (9)	0.0016 (7)	0.0081 (7)	−0.0034 (7)
C4	0.0348 (8)	0.0425 (9)	0.0414 (8)	0.0018 (7)	0.0039 (6)	−0.0003 (7)
C5	0.0338 (8)	0.0392 (8)	0.0400 (8)	−0.0034 (6)	0.0037 (6)	−0.0064 (7)
C6	0.0492 (10)	0.0478 (10)	0.0437 (9)	−0.0031 (8)	0.0092 (7)	−0.0024 (8)
C7	0.0649 (12)	0.0613 (13)	0.0585 (12)	−0.0019 (10)	0.0278 (10)	−0.0102 (10)
C8	0.0611 (12)	0.0532 (12)	0.0809 (15)	0.0065 (9)	0.0288 (11)	−0.0152 (11)
C9	0.0586 (12)	0.0441 (10)	0.0721 (13)	0.0091 (9)	0.0146 (10)	0.0006 (9)
C10	0.0497 (10)	0.0438 (9)	0.0488 (10)	0.0032 (8)	0.0137 (8)	0.0000 (8)
C11	0.0419 (9)	0.0380 (8)	0.0417 (9)	0.0028 (7)	0.0050 (7)	−0.0043 (7)
C12	0.0537 (11)	0.0559 (11)	0.0476 (10)	0.0048 (9)	0.0116 (8)	0.0013 (8)
C13	0.0863 (16)	0.0677 (14)	0.0491 (11)	0.0121 (12)	0.0206 (11)	0.0103 (10)
C14	0.0961 (18)	0.0593 (13)	0.0482 (11)	0.0194 (12)	−0.0048 (11)	0.0061 (10)
C15	0.0671 (13)	0.0611 (13)	0.0645 (13)	0.0106 (11)	−0.0164 (11)	0.0007 (11)
C16	0.0463 (10)	0.0524 (11)	0.0563 (11)	0.0009 (8)	−0.0012 (8)	0.0000 (9)
C17	0.0342 (8)	0.0416 (9)	0.0407 (8)	0.0029 (6)	0.0075 (6)	−0.0035 (7)
C18	0.0424 (9)	0.0489 (10)	0.0666 (12)	0.0069 (8)	0.0012 (8)	0.0009 (9)
C19	0.0389 (10)	0.0703 (14)	0.0857 (16)	0.0131 (9)	−0.0029 (10)	−0.0011 (12)
C20	0.0337 (9)	0.0781 (15)	0.0817 (15)	−0.0045 (9)	0.0069 (9)	−0.0137 (12)
C21	0.0439 (10)	0.0561 (12)	0.0834 (15)	−0.0091 (9)	0.0156 (10)	−0.0023 (10)
C22	0.0373 (9)	0.0447 (9)	0.0616 (11)	0.0016 (7)	0.0115 (8)	0.0017 (8)

Geometric parameters (Å, º)

O1—C1	1.213 (2)	C11—C12	1.383 (3)
O2—C3	1.216 (2)	C11—C16	1.396 (2)
C1—C11	1.493 (2)	C12—C13	1.394 (3)
C1—C2	1.524 (2)	C12—H12	0.9300
C2—C3	1.527 (2)	C13—C14	1.373 (4)
C2—C4	1.539 (2)	C13—H13	0.9300
C2—H2	0.9800	C14—C15	1.377 (4)
C3—C17	1.492 (2)	C14—H14	0.9300
C4—C5	1.515 (2)	C15—C16	1.380 (3)
C4—H4A	0.9700	C15—H15	0.9300
C4—H4B	0.9700	C16—H16	0.9300
C5—C10	1.386 (2)	C17—C22	1.389 (2)
C5—C6	1.390 (2)	C17—C18	1.394 (2)
C6—C7	1.379 (3)	C18—C19	1.376 (3)
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.380 (3)	C19—C20	1.372 (3)
C7—H7	0.9300	C19—H19	0.9300
C8—C9	1.372 (3)	C20—C21	1.378 (3)
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.387 (3)	C21—C22	1.391 (3)
C9—H9	0.9300	C21—H21	0.9300
C10—H10	0.9300	C22—H22	0.9300
O1—C1—C11	120.89 (15)	C12—C11—C16	119.31 (17)
O1—C1—C2	120.27 (15)	C12—C11—C1	122.76 (16)
C11—C1—C2	118.82 (14)	C16—C11—C1	117.92 (16)
C1—C2—C3	110.29 (13)	C11—C12—C13	120.2 (2)
C1—C2—C4	110.71 (13)	C11—C12—H12	119.9
C3—C2—C4	107.62 (13)	C13—C12—H12	119.9
C1—C2—H2	109.4	C14—C13—C12	119.6 (2)
C3—C2—H2	109.4	C14—C13—H13	120.2
C4—C2—H2	109.4	C12—C13—H13	120.2
O2—C3—C17	120.95 (15)	C13—C14—C15	120.8 (2)
O2—C3—C2	120.26 (15)	C13—C14—H14	119.6
C17—C3—C2	118.67 (14)	C15—C14—H14	119.6
C5—C4—C2	114.76 (13)	C14—C15—C16	119.8 (2)
C5—C4—H4A	108.6	C14—C15—H15	120.1
C2—C4—H4A	108.6	C16—C15—H15	120.1
C5—C4—H4B	108.6	C15—C16—C11	120.2 (2)
C2—C4—H4B	108.6	C15—C16—H16	119.9
H4A—C4—H4B	107.6	C11—C16—H16	119.9
C10—C5—C6	117.89 (16)	C22—C17—C18	119.04 (16)
C10—C5—C4	123.02 (15)	C22—C17—C3	122.97 (15)
C6—C5—C4	119.05 (15)	C18—C17—C3	117.99 (16)
C7—C6—C5	121.22 (18)	C19—C18—C17	120.18 (19)
C7—C6—H6	119.4	C19—C18—H18	119.9
C5—C6—H6	119.4	C17—C18—H18	119.9
C6—C7—C8	120.12 (19)	C20—C19—C18	120.56 (19)
C6—C7—H7	119.9	C20—C19—H19	119.7
C8—C7—H7	119.9	C18—C19—H19	119.7
C9—C8—C7	119.49 (18)	C19—C20—C21	120.18 (18)
C9—C8—H8	120.3	C19—C20—H20	119.9
C7—C8—H8	120.3	C21—C20—H20	119.9
C8—C9—C10	120.39 (19)	C20—C21—C22	119.9 (2)
C8—C9—H9	119.8	C20—C21—H21	120.1
C10—C9—H9	119.8	C22—C21—H21	120.1
C5—C10—C9	120.88 (17)	C17—C22—C21	120.15 (17)
C5—C10—H10	119.6	C17—C22—H22	119.9
C9—C10—H10	119.6	C21—C22—H22	119.9
O1—C1—C2—C3	−90.42 (18)	O1—C1—C11—C16	−18.7 (2)
C11—C1—C2—C3	91.34 (17)	C2—C1—C11—C16	159.48 (16)
O1—C1—C2—C4	28.6 (2)	C16—C11—C12—C13	1.3 (3)
C11—C1—C2—C4	−149.66 (14)	C1—C11—C12—C13	−179.85 (18)
C1—C2—C3—O2	25.7 (2)	C11—C12—C13—C14	−1.2 (3)
C4—C2—C3—O2	−95.17 (19)	C12—C13—C14—C15	−0.1 (3)
C1—C2—C3—C17	−158.27 (14)	C13—C14—C15—C16	1.4 (4)
C4—C2—C3—C17	80.87 (18)	C14—C15—C16—C11	−1.3 (3)
C1—C2—C4—C5	62.37 (18)	C12—C11—C16—C15	0.0 (3)
C3—C2—C4—C5	−177.03 (13)	C1—C11—C16—C15	−178.94 (17)
C2—C4—C5—C10	26.2 (2)	O2—C3—C17—C22	−155.02 (18)
C2—C4—C5—C6	−155.96 (15)	C2—C3—C17—C22	29.0 (2)
C10—C5—C6—C7	0.5 (3)	O2—C3—C17—C18	24.2 (3)
C4—C5—C6—C7	−177.46 (17)	C2—C3—C17—C18	−151.86 (16)
C5—C6—C7—C8	−0.5 (3)	C22—C17—C18—C19	−0.9 (3)
C6—C7—C8—C9	0.2 (3)	C3—C17—C18—C19	179.89 (18)
C7—C8—C9—C10	0.1 (3)	C17—C18—C19—C20	0.2 (3)
C6—C5—C10—C9	−0.2 (3)	C18—C19—C20—C21	1.1 (4)
C4—C5—C10—C9	177.66 (17)	C19—C20—C21—C22	−1.6 (3)
C8—C9—C10—C5	−0.1 (3)	C18—C17—C22—C21	0.4 (3)
O1—C1—C11—C12	162.35 (17)	C3—C17—C22—C21	179.53 (17)
C2—C1—C11—C12	−19.4 (2)	C20—C21—C22—C17	0.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2^i	0.93	2.63	3.498 (2)	155
C2—H2···O2^i	0.98	2.60	3.576 (2)	173
C22—H22···O2^i	0.93	2.58	3.513 (2)	177
C21—H21···O1^i	0.93	2.74	3.491 (3)	139
C6—H6···O1^ii	0.93	2.72	3.401 (2)	131

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