1,5-Di­phenyl­pent-4-ene-1,3-dione

Arrieta, A.F.; Mostad, A.

doi:10.1107/S160053680201930X

1,5-Diphenylpent-4-ene-1,3-dione

The title molecule, C₁₇H₁₄O₂, exists in the enolized form and displays a strong asymmetric intramolecular hydrogen bond. The structure supports the hypothesis that the conjugation in the molecule is a determining factor for the position of the enol H atom.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201930X/ya6133sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680201930X/ya6133Isup2.hkl Contains datablock I

CCDC reference: 200786

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Key indicators

Single-crystal X-ray study
T = 152 K
Mean (C-C) = 0.004 Å
R factor = 0.044
wR factor = 0.141
Data-to-parameter ratio = 7.1

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No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSMU_01  Alert C The ratio of given/expected absorption coefficient lies
          outside the range 0.99 <> 1.01
          Calculated value of mu =     0.084
          Value of mu given      =     0.080

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.50
         From the CIF: _reflns_number_total               1622
         Count of symmetry unique reflns         1625
         Completeness (_total/calc)             99.82%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

1,5-diphenylpent-4-ene-1,3-dione top

Crystal data top

C₁₇H₁₄O₂	D_x = 1.298 Mg m⁻³
M_r = 250.28	Melting point: 371 K
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 30.102 (6) Å	Cell parameters from 1024 reflections
b = 5.712 (1) Å	θ = 2.0–28.0°
c = 7.466 (2) Å	µ = 0.08 mm⁻¹
β = 93.97 (3)°	T = 152 K
V = 1280.7 (4) Å³	Plate, yellow
Z = 4	0.5 × 0.2 × 0.1 mm
F(000) = 528

Data collection top

Bruker P4 diffractometer	1622 independent reflections
Radiation source: fine-focus sealed tube	1419 reflections with I > 2σ(I)'
Graphite monochromator	R_int = 0.044
Detector resolution: 8 pixels mm^-1	θ_max = 28.5°, θ_min = 1.4°
ω scans	h = −40→40
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1997a)	k = −7→7
T_min = 0.959, T_max = 0.992	l = −9→9
8368 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	All H-atom parameters refined
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.0899P)² + 0.0642P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.005
1622 reflections	Δρ_max = 0.27 e Å⁻³
228 parameters	Δρ_min = −0.25 e Å⁻³
2 restraints

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

	x	y	z	U_iso*/U_eq
O1	0.43996 (7)	1.5204 (4)	0.2864 (3)	0.0427 (6)
O2	0.36220 (7)	1.3790 (4)	0.2153 (3)	0.0418 (6)
H20	0.392 (3)	1.463 (12)	0.219 (10)	0.11 (2)*
C1	0.52881 (8)	1.4566 (5)	0.3905 (3)	0.0292 (5)
C2	0.57307 (9)	1.4277 (5)	0.4519 (4)	0.0308 (6)
C3	0.58658 (9)	1.2290 (5)	0.5475 (3)	0.0308 (6)
C4	0.55578 (9)	1.0562 (5)	0.5817 (4)	0.0319 (6)
C5	0.51115 (9)	1.0846 (5)	0.5192 (4)	0.0298 (5)
C6	0.49746 (8)	1.2851 (5)	0.4236 (3)	0.0260 (5)
C7	0.45026 (8)	1.3236 (5)	0.3530 (3)	0.0292 (5)
C8	0.41784 (9)	1.1428 (5)	0.3606 (4)	0.0324 (6)
C9	0.37441 (8)	1.1806 (5)	0.2926 (3)	0.0297 (5)
C10	0.34033 (9)	1.0036 (4)	0.3080 (4)	0.0308 (6)
C11	0.29738 (9)	1.0397 (4)	0.2512 (3)	0.0278 (5)
C12	0.26026 (8)	0.8785 (4)	0.2712 (3)	0.0262 (5)
C13	0.26575 (8)	0.6607 (5)	0.3547 (3)	0.0278 (5)
C14	0.22917 (9)	0.5199 (5)	0.3806 (4)	0.0303 (6)
C15	0.18663 (9)	0.5927 (5)	0.3226 (4)	0.0316 (6)
C16	0.18041 (8)	0.8067 (5)	0.2366 (4)	0.0320 (6)
C17	0.21696 (8)	0.9485 (4)	0.2101 (3)	0.0278 (5)
H1	0.5207 (10)	1.609 (5)	0.329 (4)	0.018 (7)*
H2	0.5929 (14)	1.547 (7)	0.431 (5)	0.040 (9)*
H3	0.6179 (11)	1.222 (6)	0.591 (4)	0.027 (7)*
H4	0.5665 (16)	0.916 (8)	0.653 (6)	0.057 (12)*
H5	0.4900 (12)	0.962 (6)	0.552 (5)	0.034 (9)*
H17	0.2106 (13)	1.110 (6)	0.147 (5)	0.036 (9)*
H8	0.4255 (13)	0.990 (7)	0.426 (5)	0.034 (9)*
H10	0.3482 (12)	0.868 (7)	0.376 (5)	0.040 (10)*
H11	0.2894 (10)	1.203 (5)	0.192 (4)	0.022 (7)*
H13	0.2944 (11)	0.608 (5)	0.395 (4)	0.023 (7)*
H14	0.2320 (9)	0.384 (5)	0.443 (4)	0.012 (6)*
H15	0.1598 (18)	0.517 (9)	0.348 (7)	0.064 (13)*
H16	0.1499 (14)	0.860 (8)	0.193 (6)	0.048 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0284 (9)	0.0348 (10)	0.0638 (15)	−0.0031 (8)	−0.0049 (9)	0.0175 (10)
O2	0.0273 (9)	0.0367 (11)	0.0602 (14)	−0.0041 (8)	−0.0055 (9)	0.0138 (9)
C1	0.0292 (12)	0.0296 (12)	0.0284 (13)	−0.0015 (10)	0.0000 (10)	0.0009 (9)
C2	0.0280 (12)	0.0342 (12)	0.0302 (13)	−0.0046 (11)	0.0016 (10)	0.0002 (10)
C3	0.0244 (11)	0.0373 (13)	0.0305 (13)	0.0036 (10)	−0.0007 (9)	−0.0023 (10)
C4	0.0315 (13)	0.0331 (13)	0.0306 (13)	0.0056 (10)	−0.0020 (10)	0.0011 (10)
C5	0.0261 (12)	0.0310 (12)	0.0321 (13)	−0.0010 (10)	0.0013 (10)	0.0009 (10)
C6	0.0237 (10)	0.0266 (11)	0.0275 (12)	−0.0010 (9)	−0.0001 (9)	−0.0020 (9)
C7	0.0242 (11)	0.0310 (12)	0.0323 (13)	0.0005 (9)	0.0006 (10)	0.0019 (10)
C8	0.0275 (11)	0.0279 (11)	0.0412 (15)	−0.0013 (10)	−0.0024 (10)	0.0027 (10)
C9	0.0253 (11)	0.0314 (12)	0.0323 (13)	−0.0008 (9)	0.0009 (10)	0.0005 (10)
C10	0.0290 (12)	0.0281 (13)	0.0349 (14)	−0.0031 (9)	−0.0006 (10)	0.0009 (10)
C11	0.0264 (11)	0.0288 (11)	0.0277 (12)	−0.0021 (9)	−0.0008 (9)	0.0010 (10)
C12	0.0228 (11)	0.0288 (12)	0.0265 (12)	−0.0018 (9)	−0.0011 (9)	−0.0026 (9)
C13	0.0270 (11)	0.0291 (11)	0.0268 (11)	0.0015 (9)	−0.0021 (9)	−0.0013 (10)
C14	0.0360 (14)	0.0268 (12)	0.0279 (13)	−0.0023 (10)	0.0002 (10)	−0.0019 (10)
C15	0.0289 (12)	0.0341 (13)	0.0316 (13)	−0.0060 (10)	0.0016 (10)	−0.0046 (10)
C16	0.0243 (11)	0.0391 (14)	0.0323 (13)	−0.0004 (10)	−0.0013 (10)	−0.0046 (10)
C17	0.0251 (11)	0.0293 (11)	0.0286 (13)	0.0019 (9)	−0.0022 (9)	−0.0022 (10)

Geometric parameters (Å, º) top

O1—C7	1.259 (3)	C8—H8	1.02 (4)
O2—C9	1.313 (3)	C9—C10	1.451 (3)
O2—H20	1.02 (8)	C10—C11	1.348 (4)
C1—C2	1.388 (4)	C10—H10	0.95 (4)
C1—C6	1.394 (3)	C11—C12	1.463 (3)
C1—H1	1.00 (3)	C11—H11	1.05 (3)
C2—C3	1.386 (4)	C12—C13	1.396 (4)
C2—H2	0.93 (4)	C12—C17	1.409 (3)
C3—C4	1.390 (4)	C13—C14	1.388 (3)
C3—H3	0.98 (4)	C13—H13	0.94 (4)
C4—C5	1.401 (4)	C14—C15	1.387 (4)
C4—H4	1.00 (4)	C14—H14	0.91 (3)
C5—C6	1.396 (4)	C15—C16	1.388 (5)
C5—H5	0.99 (4)	C15—H15	0.95 (4)
C6—C7	1.497 (3)	C16—C17	1.391 (4)
C7—C8	1.425 (3)	C16—H16	1.00 (4)
C8—C9	1.386 (4)	C17—H17	1.05 (4)

C9—O2—H20	100 (4)	O2—C9—C10	117.3 (2)
C2—C1—C6	120.2 (2)	C8—C9—C10	121.1 (2)
C2—C1—H1	116 (2)	C11—C10—C9	122.5 (2)
C6—C1—H1	123 (2)	C11—C10—H10	120 (2)
C3—C2—C1	120.5 (3)	C9—C10—H10	117 (2)
C3—C2—H2	121 (2)	C10—C11—C12	126.4 (2)
C1—C2—H2	118 (2)	C10—C11—H11	117 (2)
C2—C3—C4	120.0 (2)	C12—C11—H11	117 (2)
C2—C3—H3	117 (2)	C13—C12—C17	118.4 (2)
C4—C3—H3	123 (2)	C13—C12—C11	122.6 (2)
C3—C4—C5	119.5 (2)	C17—C12—C11	119.0 (2)
C3—C4—H4	118 (3)	C14—C13—C12	120.5 (2)
C5—C4—H4	122 (3)	C14—C13—H13	119 (2)
C6—C5—C4	120.5 (2)	C12—C13—H13	120 (2)
C6—C5—H5	122 (2)	C15—C14—C13	120.5 (2)
C4—C5—H5	117 (2)	C15—C14—H14	118 (2)
C1—C6—C5	119.2 (2)	C13—C14—H14	121 (2)
C1—C6—C7	118.2 (2)	C14—C15—C16	120.1 (2)
C5—C6—C7	122.7 (2)	C14—C15—H15	126 (3)
O1—C7—C8	120.8 (2)	C16—C15—H15	114 (3)
O1—C7—C6	118.2 (2)	C15—C16—C17	119.8 (2)
C8—C7—C6	121.0 (2)	C15—C16—H16	121 (2)
C9—C8—C7	120.2 (2)	C17—C16—H16	120 (2)
C9—C8—H8	119 (2)	C16—C17—C12	120.8 (2)
C7—C8—H8	120 (2)	C16—C17—H17	117 (2)
O2—C9—C8	121.6 (2)	C12—C17—H17	122 (2)

C6—C1—C2—C3	−0.3 (4)	C7—C8—C9—C10	−176.5 (2)
C1—C2—C3—C4	0.3 (4)	O2—C9—C10—C11	−2.0 (4)
C2—C3—C4—C5	−0.1 (4)	C8—C9—C10—C11	176.6 (3)
C3—C4—C5—C6	−0.2 (4)	C9—C10—C11—C12	−175.8 (2)
C2—C1—C6—C5	0.1 (4)	C10—C11—C12—C13	−0.2 (4)
C2—C1—C6—C7	−179.4 (2)	C10—C11—C12—C17	177.5 (3)
C4—C5—C6—C1	0.2 (4)	C17—C12—C13—C14	−1.7 (4)
C4—C5—C6—C7	179.7 (2)	C11—C12—C13—C14	176.0 (2)
C1—C6—C7—O1	−8.4 (4)	C12—C13—C14—C15	0.5 (4)
C5—C6—C7—O1	172.1 (3)	C13—C14—C15—C16	0.5 (4)
C1—C6—C7—C8	171.5 (2)	C14—C15—C16—C17	−0.5 (4)
C5—C6—C7—C8	−8.0 (4)	C15—C16—C17—C12	−0.7 (4)
O1—C7—C8—C9	0.7 (4)	C13—C12—C17—C16	1.7 (4)
C6—C7—C8—C9	−179.2 (2)	C11—C12—C17—C16	−176.0 (2)
C7—C8—C9—O2	2.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H20···O1	1.02 (8)	1.53 (8)	2.498 (3)	157 (7)
C1—H1···C5ⁱ	1.00 (3)	2.90 (3)	3.825 (4)	153 (2)
C4—H4···C2ⁱⁱ	1.00 (5)	2.97 (5)	3.918 (4)	158 (4)
C14—H14···C17ⁱⁱⁱ	0.91 (3)	2.81 (3)	3.670 (4)	158 (2)
C17—H17···C14^iv	1.05 (4)	2.98 (4)	3.941 (4)	152 (3)

Symmetry codes: (i) x, −y+3, z−1/2; (ii) x, −y+2, z+1/2; (iii) x, −y+1, z+1/2; (iv) x, −y+2, z−1/2.

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1,5-Di­phenyl­pent-4-ene-1,3-dione

Supporting information

Key indicators

checkCIF results

1,5-Diphenylpent-4-ene-1,3-dione