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The asymmetric unit in the crystal structure of the monoclinic form of 6-phenyl­hex-5-ene-2,4-dione, C12H12O2, consists of two independent mol­ecules. Both mol­ecules exist in the enolized form and show a strong asymmetric intramolecular hydrogen bond. The intermolecular C—H...O contacts represent the most prominent feature of the crystal packing of the compound.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000995/ya6084sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000995/ya6084Isup2.hkl
Contains datablock I

CCDC reference: 180804

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.070
  • wR factor = 0.228
  • Data-to-parameter ratio = 10.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
ABSMU_01 Alert B The ratio of given/expected absorption coefficient lies outside the range 0.95 <> 1.05 Calculated value of mu = 0.084 Value of mu given = 0.080 THETM_01 Alert B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5565
0 Alert Level A = Potentially serious problem
2 Alert Level B = Potential problem
0 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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

6-phenylhex-5-ene-2,3-dione top
Crystal data top
C12H12O2Dx = 1.253 Mg m3
Mr = 188.22Melting point: 356 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.8222 (14) ÅCell parameters from 1024 reflections
b = 5.8033 (6) Åθ = 2.0–23.0°
c = 25.240 (3) ŵ = 0.08 mm1
β = 99.663 (4)°T = 150 K
V = 1995.9 (4) Å3Needle, yellow
Z = 80.2 × 0.1 × 0.1 mm
F(000) = 800
Data collection top
Bruker SMART
diffractometer
2874 independent reflections
Radiation source: fine-focus sealed tube2017 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
Detector resolution: 8 pixels mm-1θmax = 23.3°, θmin = 1.5°
ω scansh = 1515
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1997)
k = 56
Tmin = 0.983, Tmax = 0.992l = 2828
14200 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.228H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.1069P)2 + 3.0387P]
where P = (Fo2 + 2Fc2)/3
2874 reflections(Δ/σ)max = 0.007
283 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.32 e Å3
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
xyzUiso*/Ueq
O1A0.3615 (2)0.8718 (5)0.01245 (10)0.0506 (8)
O2A0.3590 (2)0.7091 (5)0.07879 (11)0.0455 (8)
H2OA0.364 (3)0.736 (8)0.042 (2)0.055*
C1A0.3819 (4)1.2705 (9)0.02847 (18)0.0484 (11)
H1A10.403 (4)1.229 (11)0.058 (3)0.10 (2)*
H1A20.411 (6)1.420 (14)0.014 (3)0.14 (3)*
H1A30.314 (6)1.347 (13)0.037 (3)0.14 (3)*
C2A0.3732 (3)1.0720 (7)0.00761 (15)0.0370 (9)
C3A0.3794 (3)1.1044 (7)0.06408 (14)0.0365 (9)
H3A0.38841.25550.07850.044*
C4A0.3726 (3)0.9237 (6)0.09785 (14)0.0324 (9)
C5A0.3798 (3)0.9470 (6)0.15563 (14)0.0337 (9)
H5A0.39671.09350.17130.040*
C6A0.3639 (3)0.7742 (7)0.18804 (14)0.0334 (9)
H6A0.34430.63160.17110.040*
C7A0.3731 (3)0.7793 (6)0.24656 (14)0.0298 (8)
C8A0.4134 (3)0.9644 (7)0.27821 (14)0.0355 (9)
H8A0.43551.09630.26150.043*
C9A0.4216 (3)0.9584 (7)0.33368 (14)0.0380 (10)
H9A0.45071.08450.35450.046*
C10A0.3877 (3)0.7705 (7)0.35911 (15)0.0373 (9)
H10A0.39210.76840.39710.045*
C11A0.3477 (3)0.5871 (7)0.32844 (14)0.0377 (9)
H11A0.32400.45730.34530.045*
C12A0.3418 (3)0.5907 (7)0.27325 (15)0.0365 (9)
H12A0.31570.46060.25290.044*
O1B0.1526 (2)0.3745 (5)0.01527 (11)0.0533 (8)
O2B0.1508 (2)0.2026 (5)0.10613 (11)0.0530 (9)
H2OB0.154 (3)0.237 (8)0.066 (2)0.064*
C1B0.1131 (4)0.7653 (10)0.00573 (19)0.0517 (12)
H1B10.178 (5)0.794 (11)0.019 (3)0.11 (2)*
H1B20.099 (5)0.887 (12)0.006 (3)0.10 (2)*
H1B30.059 (7)0.733 (16)0.034 (4)0.18 (4)*
C2B0.1281 (3)0.5652 (7)0.03236 (15)0.0403 (10)
C3B0.1145 (3)0.5898 (7)0.08683 (14)0.0382 (10)
H3B0.09740.73660.09910.046*
C4B0.1254 (3)0.4087 (6)0.12194 (14)0.0347 (9)
C5B0.1132 (3)0.4280 (7)0.17771 (14)0.0347 (9)
H5B0.08990.56950.18970.042*
C6B0.1333 (3)0.2557 (7)0.21301 (14)0.0349 (9)
H6B0.15410.11470.19940.042*
C7B0.1266 (3)0.2604 (6)0.27056 (14)0.0328 (9)
C8B0.0868 (3)0.4451 (7)0.29467 (14)0.0358 (9)
H8B0.06190.57430.27360.043*
C9B0.0833 (3)0.4425 (7)0.34928 (15)0.0410 (10)
H9B0.05480.56840.36520.049*
C10B0.1210 (3)0.2572 (7)0.38081 (15)0.0405 (10)
H10B0.11960.25660.41830.049*
C11B0.1603 (3)0.0746 (7)0.35719 (15)0.0401 (10)
H11B0.18650.05250.37860.048*
C12B0.1623 (3)0.0729 (7)0.30278 (15)0.0381 (9)
H12B0.18820.05700.28700.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.073 (2)0.0495 (19)0.0292 (15)0.0005 (15)0.0092 (13)0.0075 (14)
O2A0.0672 (19)0.0391 (17)0.0306 (15)0.0015 (14)0.0092 (13)0.0053 (13)
C1A0.067 (3)0.049 (3)0.030 (2)0.002 (2)0.010 (2)0.004 (2)
C2A0.039 (2)0.042 (2)0.030 (2)0.0034 (17)0.0026 (16)0.0006 (18)
C3A0.047 (2)0.035 (2)0.0274 (19)0.0028 (18)0.0049 (16)0.0044 (16)
C4A0.035 (2)0.034 (2)0.0271 (19)0.0017 (16)0.0040 (15)0.0015 (16)
C5A0.046 (2)0.028 (2)0.0260 (19)0.0023 (17)0.0031 (15)0.0034 (16)
C6A0.034 (2)0.035 (2)0.0296 (19)0.0015 (17)0.0019 (15)0.0040 (17)
C7A0.0332 (19)0.029 (2)0.0271 (18)0.0042 (16)0.0047 (14)0.0011 (15)
C8A0.041 (2)0.034 (2)0.033 (2)0.0024 (17)0.0070 (16)0.0046 (17)
C9A0.043 (2)0.043 (2)0.0279 (19)0.0013 (18)0.0033 (16)0.0051 (18)
C10A0.041 (2)0.044 (2)0.0267 (19)0.0052 (18)0.0044 (16)0.0028 (18)
C11A0.040 (2)0.042 (2)0.032 (2)0.0024 (18)0.0074 (16)0.0084 (17)
C12A0.035 (2)0.037 (2)0.036 (2)0.0007 (17)0.0040 (16)0.0014 (17)
O1B0.078 (2)0.0515 (19)0.0316 (15)0.0103 (16)0.0132 (14)0.0020 (14)
O2B0.082 (2)0.0481 (19)0.0311 (16)0.0088 (16)0.0156 (14)0.0020 (13)
C1B0.071 (3)0.049 (3)0.037 (2)0.002 (3)0.014 (2)0.006 (2)
C2B0.043 (2)0.046 (3)0.032 (2)0.0010 (19)0.0052 (16)0.0016 (19)
C3B0.049 (2)0.036 (2)0.031 (2)0.0023 (18)0.0085 (17)0.0017 (17)
C4B0.038 (2)0.037 (2)0.0293 (19)0.0003 (17)0.0063 (16)0.0042 (17)
C5B0.041 (2)0.035 (2)0.0286 (19)0.0006 (17)0.0059 (16)0.0031 (17)
C6B0.033 (2)0.042 (2)0.030 (2)0.0008 (17)0.0058 (15)0.0057 (18)
C7B0.033 (2)0.034 (2)0.031 (2)0.0034 (16)0.0036 (15)0.0019 (17)
C8B0.039 (2)0.041 (2)0.0276 (19)0.0011 (17)0.0054 (15)0.0035 (17)
C9B0.046 (2)0.044 (2)0.034 (2)0.0022 (19)0.0112 (17)0.0064 (18)
C10B0.045 (2)0.049 (2)0.028 (2)0.004 (2)0.0073 (16)0.0021 (18)
C11B0.041 (2)0.042 (2)0.037 (2)0.0011 (18)0.0062 (17)0.0081 (18)
C12B0.040 (2)0.038 (2)0.037 (2)0.0004 (17)0.0079 (17)0.0019 (17)
Geometric parameters (Å, º) top
O1A—C2A1.267 (5)O1B—C2B1.255 (5)
O2A—C4A1.337 (4)O2B—C4B1.326 (5)
O2A—H2OA0.95 (5)O2B—H2OB1.05 (5)
C1A—C2A1.486 (6)C1B—C2B1.500 (6)
C1A—H1A10.88 (7)C1B—H1B11.02 (7)
C1A—H1A21.00 (8)C1B—H1B20.81 (7)
C1A—H1A31.03 (8)C1B—H1B30.97 (9)
C2A—C3A1.426 (5)C2B—C3B1.426 (5)
C3A—C4A1.364 (5)C3B—C4B1.367 (5)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.451 (5)C4B—C5B1.450 (5)
C5A—C6A1.336 (5)C5B—C6B1.337 (5)
C5A—H5A0.9500C5B—H5B0.9500
C6A—C7A1.461 (5)C6B—C7B1.471 (5)
C6A—H6A0.9500C6B—H6B0.9500
C7A—C12A1.391 (5)C7B—C8B1.391 (5)
C7A—C8A1.397 (5)C7B—C12B1.398 (5)
C8A—C9A1.386 (5)C8B—C9B1.388 (5)
C8A—H8A0.9500C8B—H8B0.9500
C9A—C10A1.386 (6)C9B—C10B1.387 (6)
C9A—H9A0.9500C9B—H9B0.9500
C10A—C11A1.377 (6)C10B—C11B1.372 (6)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.382 (5)C11B—C12B1.378 (5)
C11A—H11A0.9500C11B—H11B0.9500
C12A—H12A0.9500C12B—H12B0.9500
C4A—O2A—H2OA100 (3)C4B—O2B—H2OB100 (3)
C2A—C1A—H1A1113 (4)C2B—C1B—H1B1108 (4)
C2A—C1A—H1A2122 (4)C2B—C1B—H1B2117 (5)
H1A1—C1A—H1A2112 (6)H1B1—C1B—H1B2106 (6)
C2A—C1A—H1A3108 (4)C2B—C1B—H1B3109 (6)
H1A1—C1A—H1A3110 (6)H1B1—C1B—H1B3113 (6)
H1A2—C1A—H1A390 (5)H1B2—C1B—H1B3104 (7)
O1A—C2A—C3A120.2 (4)O1B—C2B—C3B120.4 (4)
O1A—C2A—C1A119.0 (3)O1B—C2B—C1B118.6 (4)
C3A—C2A—C1A120.9 (4)C3B—C2B—C1B120.9 (4)
C4A—C3A—C2A121.6 (4)C4B—C3B—C2B122.0 (4)
C4A—C3A—H3A119.2C4B—C3B—H3B119.0
C2A—C3A—H3A119.2C2B—C3B—H3B119.0
O2A—C4A—C3A120.7 (3)O2B—C4B—C3B120.3 (3)
O2A—C4A—C5A115.5 (3)O2B—C4B—C5B116.2 (3)
C3A—C4A—C5A123.8 (3)C3B—C4B—C5B123.5 (3)
C6A—C5A—C4A123.7 (3)C6B—C5B—C4B122.9 (4)
C6A—C5A—H5A118.1C6B—C5B—H5B118.5
C4A—C5A—H5A118.1C4B—C5B—H5B118.5
C5A—C6A—C7A127.5 (4)C5B—C6B—C7B127.1 (4)
C5A—C6A—H6A116.3C5B—C6B—H6B116.4
C7A—C6A—H6A116.3C7B—C6B—H6B116.4
C12A—C7A—C8A117.0 (3)C8B—C7B—C12B118.2 (3)
C12A—C7A—C6A119.5 (3)C8B—C7B—C6B122.8 (3)
C8A—C7A—C6A123.5 (3)C12B—C7B—C6B119.1 (3)
C9A—C8A—C7A121.0 (4)C9B—C8B—C7B120.6 (4)
C9A—C8A—H8A119.5C9B—C8B—H8B119.7
C7A—C8A—H8A119.5C7B—C8B—H8B119.7
C8A—C9A—C10A120.7 (4)C10B—C9B—C8B120.4 (4)
C8A—C9A—H9A119.6C10B—C9B—H9B119.8
C10A—C9A—H9A119.6C8B—C9B—H9B119.8
C11A—C10A—C9A118.9 (3)C11B—C10B—C9B119.2 (3)
C11A—C10A—H10A120.6C11B—C10B—H10B120.4
C9A—C10A—H10A120.6C9B—C10B—H10B120.4
C10A—C11A—C12A120.3 (4)C10B—C11B—C12B120.9 (4)
C10A—C11A—H11A119.8C10B—C11B—H11B119.5
C12A—C11A—H11A119.8C12B—C11B—H11B119.5
C11A—C12A—C7A122.0 (4)C11B—C12B—C7B120.7 (4)
C11A—C12A—H12A119.0C11B—C12B—H12B119.7
C7A—C12A—H12A119.0C7B—C12B—H12B119.7
O1A—C2A—C3A—C4A0.3 (6)O1B—C2B—C3B—C4B1.4 (6)
C1A—C2A—C3A—C4A179.3 (4)C1B—C2B—C3B—C4B178.4 (4)
C2A—C3A—C4A—O2A0.5 (6)C2B—C3B—C4B—O2B1.1 (6)
C2A—C3A—C4A—C5A179.1 (4)C2B—C3B—C4B—C5B179.3 (4)
O2A—C4A—C5A—C6A7.0 (6)O2B—C4B—C5B—C6B5.0 (6)
C3A—C4A—C5A—C6A173.4 (4)C3B—C4B—C5B—C6B173.3 (4)
C4A—C5A—C6A—C7A177.4 (3)C4B—C5B—C6B—C7B177.8 (3)
C5A—C6A—C7A—C12A172.1 (4)C5B—C6B—C7B—C8B7.4 (6)
C5A—C6A—C7A—C8A8.8 (6)C5B—C6B—C7B—C12B172.0 (4)
C12A—C7A—C8A—C9A0.0 (5)C12B—C7B—C8B—C9B0.3 (6)
C6A—C7A—C8A—C9A179.1 (3)C6B—C7B—C8B—C9B179.2 (4)
C7A—C8A—C9A—C10A1.6 (6)C7B—C8B—C9B—C10B1.2 (6)
C8A—C9A—C10A—C11A1.4 (6)C8B—C9B—C10B—C11B1.1 (6)
C9A—C10A—C11A—C12A0.2 (6)C9B—C10B—C11B—C12B0.3 (6)
C10A—C11A—C12A—C7A1.8 (6)C10B—C11B—C12B—C7B1.7 (6)
C8A—C7A—C12A—C11A1.6 (5)C8B—C7B—C12B—C11B1.7 (5)
C6A—C7A—C12A—C11A179.2 (3)C6B—C7B—C12B—C11B177.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2OA···O1A0.95 (5)1.59 (5)2.495 (4)159 (4)
O2B—H2OB···O1B1.05 (5)1.50 (5)2.505 (4)158 (4)
C1B—H1B1···O1A1.02 (7)2.55 (7)3.520 (7)157 (5)
C10B—H10B···O1Bi0.952.533.434 (5)159
C10A—H10A···O1Aii0.952.533.423 (5)158
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+3/2, z+1/2.
 

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