(Z)-3-(4-Methyl­benzyl­idene)-4-oxo­penta­noic acid

The title compound, C₁₃H₁₄O₃, a levulinic acid derivative, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The compound adopts a Z configuration about the C=C bonds in both mol­ecules. The dihedral angle between the toluene ring and the carb­oxy­lic acid group is 72.83 (7)° in mol­ecule A and 83.64 (8)° in mol­ecule B. The toluene rings are inclined to the ketone substituents by 27.03 (9)° for A and 30.84 (6)° for B. In the crystal, like mol­ecules are linked by pairs of O—H...O hydrogen bonds, forming A–A and B-B inversion dimers.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.051
• wR factor = 0.174
• Data-to-parameter ratio = 26.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C8 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C14 Check
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C13 H14 O3
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -4.473 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  P21/a        P21/c Note
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C12 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C25 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          8 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2012) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

(Z)-3-(4-Methylbenzylidene)-4-oxopentanoic acid

Crystal data

C13H14O3	F(000) = 928
Mr = 218.25	Dx = 1.210 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
a = 9.2491 (5) Å	Cell parameters from 7673 reflections
b = 18.1423 (10) Å	θ = 2.3–31.1°
c = 14.3719 (7) Å	µ = 0.09 mm^−1
β = 96.610 (3)°	T = 296 K
V = 2395.6 (2) Å^3	Block, colourless
Z = 8	0.3 × 0.2 × 0.15 mm

Data collection

Bruker X8 APEX diffractometer	7673 independent reflections
Radiation source: fine-focus sealed tube	5039 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
Detector resolution: 7.9 pixels mm^-1	θmax = 31.1°, θmin = 2.3°
ω and φ scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −26→26
Tmin = 0.91, Tmax = 0.98	l = −18→20
129996 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.174	w = 1/[σ^2(Fo^2) + (0.0946P)^2 + 0.1975P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
7673 reflections	Δρmax = 0.31 e Å^−3
295 parameters	Δρmin = −0.16 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C16	0.13525 (12)	0.70579 (6)	0.12254 (8)	0.0392 (2)
C14	0.09904 (12)	0.57199 (6)	0.08109 (8)	0.0387 (2)
O4	−0.00001 (11)	0.58848 (5)	0.02117 (7)	0.0599 (3)
C17	0.04540 (12)	0.74580 (6)	0.16941 (8)	0.0416 (2)
H17	0.0348	0.7949	0.1511	0.050*
O5	0.14539 (12)	0.50486 (5)	0.09445 (7)	0.0624 (3)
H5	0.0926	0.4767	0.0613	0.094*
O6	0.28038 (12)	0.69915 (6)	0.00008 (8)	0.0663 (3)
C15	0.17930 (13)	0.62729 (6)	0.14503 (8)	0.0430 (2)
H15A	0.2828	0.6221	0.1412	0.052*
H15B	0.1622	0.6166	0.2090	0.052*
C18	−0.03845 (13)	0.72349 (6)	0.24511 (8)	0.0433 (3)
C24	0.20185 (13)	0.73769 (7)	0.04260 (8)	0.0453 (3)
C19	−0.09393 (16)	0.65281 (7)	0.25495 (11)	0.0574 (3)
H19	−0.0774	0.6166	0.2116	0.069*
C23	−0.07381 (15)	0.77700 (7)	0.30853 (9)	0.0518 (3)
H23	−0.0441	0.8255	0.3017	0.062*
C25	0.17203 (18)	0.81607 (8)	0.01331 (11)	0.0616 (4)
H25A	0.0695	0.8225	−0.0044	0.092*
H25B	0.2239	0.8276	−0.0390	0.092*
H25C	0.2036	0.8484	0.0646	0.092*
C22	−0.15266 (16)	0.75873 (9)	0.38157 (10)	0.0613 (4)
H22	−0.1735	0.7951	0.4236	0.074*
C21	−0.20095 (16)	0.68771 (9)	0.39341 (10)	0.0608 (3)
C20	−0.17302 (18)	0.63566 (9)	0.32788 (12)	0.0658 (4)
H20	−0.2082	0.5880	0.3329	0.079*
C26	−0.2846 (2)	0.66728 (13)	0.47373 (13)	0.0872 (6)
H26A	−0.2198	0.6452	0.5229	0.131*
H26B	−0.3600	0.6328	0.4524	0.131*
H26C	−0.3273	0.7108	0.4971	0.131*
C3	0.01570 (14)	1.08093 (7)	0.21990 (8)	0.0465 (3)
O1	0.06317 (11)	1.04595 (6)	0.41565 (7)	0.0700 (3)
O2	−0.15248 (12)	0.99179 (7)	0.40738 (8)	0.0734 (3)
H2	−0.1222	0.9794	0.4609	0.110*
C4	0.07038 (15)	1.14814 (7)	0.20654 (8)	0.0488 (3)
H4	0.1413	1.1498	0.1657	0.059*
C5	0.03529 (15)	1.21933 (7)	0.24653 (9)	0.0486 (3)
O3	0.02795 (14)	0.95429 (6)	0.19154 (10)	0.0786 (3)
C2	−0.10518 (14)	1.06384 (8)	0.27826 (9)	0.0521 (3)
H2A	−0.1592	1.1088	0.2865	0.063*
H2B	−0.1714	1.0291	0.2444	0.063*
C1	−0.05470 (14)	1.03229 (7)	0.37301 (9)	0.0498 (3)
C11	0.06928 (16)	1.01546 (7)	0.17210 (10)	0.0557 (3)
C10	0.04781 (18)	1.28227 (8)	0.19252 (11)	0.0628 (4)
H10	0.0781	1.2780	0.1333	0.075*
C9	0.0157 (2)	1.35095 (8)	0.22602 (13)	0.0708 (4)
H9	0.0228	1.3920	0.1880	0.085*
C6	−0.0045 (2)	1.22914 (8)	0.33599 (10)	0.0686 (4)
H6	−0.0104	1.1885	0.3748	0.082*
C8	−0.02629 (17)	1.36043 (8)	0.31340 (13)	0.0656 (4)
C7	−0.0355 (2)	1.29855 (9)	0.36803 (13)	0.0755 (5)
H7	−0.0632	1.3036	0.4279	0.091*
C12	0.1763 (2)	1.02402 (9)	0.10182 (14)	0.0850 (6)
H12A	0.2635	1.0468	0.1313	0.128*
H12B	0.1345	1.0543	0.0509	0.128*
H12C	0.1992	0.9764	0.0783	0.128*
C13	−0.0593 (3)	1.43579 (10)	0.35049 (19)	0.0979 (7)
H13A	−0.1600	1.4474	0.3327	0.147*
H13B	0.0007	1.4719	0.3248	0.147*
H13C	−0.0396	1.4359	0.4175	0.147*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C16	0.0393 (5)	0.0342 (5)	0.0431 (5)	−0.0027 (4)	0.0007 (4)	−0.0051 (4)
C14	0.0429 (5)	0.0330 (5)	0.0408 (5)	0.0002 (4)	0.0072 (4)	−0.0007 (4)
O4	0.0634 (6)	0.0388 (4)	0.0713 (6)	0.0057 (4)	−0.0183 (5)	−0.0112 (4)
C17	0.0439 (6)	0.0341 (5)	0.0462 (6)	−0.0009 (4)	0.0019 (4)	−0.0032 (4)
O5	0.0852 (7)	0.0319 (4)	0.0637 (6)	0.0025 (4)	−0.0193 (5)	−0.0019 (4)
O6	0.0717 (7)	0.0660 (6)	0.0657 (6)	0.0078 (5)	0.0266 (5)	−0.0053 (5)
C15	0.0436 (6)	0.0361 (5)	0.0482 (6)	0.0011 (4)	0.0008 (5)	−0.0045 (4)
C18	0.0423 (6)	0.0419 (6)	0.0455 (6)	0.0032 (4)	0.0044 (5)	−0.0032 (4)
C24	0.0433 (6)	0.0447 (6)	0.0480 (6)	−0.0051 (5)	0.0054 (5)	−0.0051 (5)
C19	0.0628 (8)	0.0451 (7)	0.0677 (8)	−0.0040 (6)	0.0215 (7)	−0.0079 (6)
C23	0.0554 (7)	0.0469 (6)	0.0534 (7)	0.0041 (5)	0.0078 (6)	−0.0071 (5)
C25	0.0718 (9)	0.0494 (7)	0.0654 (8)	−0.0062 (6)	0.0157 (7)	0.0081 (6)
C22	0.0626 (8)	0.0692 (9)	0.0538 (7)	0.0071 (7)	0.0138 (6)	−0.0123 (6)
C21	0.0527 (7)	0.0751 (9)	0.0561 (8)	0.0068 (7)	0.0134 (6)	0.0073 (7)
C20	0.0665 (9)	0.0574 (8)	0.0772 (10)	−0.0043 (7)	0.0237 (8)	0.0057 (7)
C26	0.0783 (11)	0.1172 (16)	0.0709 (11)	0.0043 (11)	0.0297 (9)	0.0171 (10)
C3	0.0565 (7)	0.0444 (6)	0.0386 (5)	0.0011 (5)	0.0052 (5)	0.0067 (4)
O1	0.0603 (6)	0.0935 (8)	0.0553 (5)	−0.0173 (5)	0.0034 (5)	0.0272 (5)
O2	0.0680 (7)	0.0907 (8)	0.0612 (6)	−0.0252 (6)	0.0072 (5)	0.0242 (6)
C4	0.0609 (7)	0.0447 (6)	0.0422 (6)	0.0004 (5)	0.0117 (5)	0.0032 (5)
C5	0.0566 (7)	0.0441 (6)	0.0461 (6)	−0.0024 (5)	0.0096 (5)	0.0031 (5)
O3	0.0910 (8)	0.0423 (5)	0.1056 (9)	−0.0033 (5)	0.0243 (7)	0.0054 (5)
C2	0.0519 (7)	0.0565 (7)	0.0480 (6)	−0.0022 (6)	0.0054 (5)	0.0083 (5)
C1	0.0531 (7)	0.0497 (6)	0.0478 (6)	−0.0048 (5)	0.0116 (5)	0.0078 (5)
C11	0.0659 (8)	0.0439 (6)	0.0575 (7)	0.0017 (6)	0.0082 (6)	0.0034 (5)
C10	0.0833 (10)	0.0482 (7)	0.0602 (8)	−0.0094 (7)	0.0223 (7)	0.0059 (6)
C9	0.0897 (11)	0.0441 (7)	0.0804 (10)	−0.0052 (7)	0.0169 (9)	0.0099 (7)
C6	0.1076 (13)	0.0497 (7)	0.0519 (8)	0.0014 (7)	0.0235 (8)	0.0034 (6)
C8	0.0626 (9)	0.0484 (7)	0.0857 (10)	0.0020 (6)	0.0081 (8)	−0.0074 (7)
C7	0.1064 (14)	0.0575 (9)	0.0670 (9)	0.0010 (8)	0.0295 (9)	−0.0100 (7)
C12	0.1175 (15)	0.0563 (9)	0.0903 (12)	0.0036 (9)	0.0507 (11)	−0.0076 (8)
C13	0.1082 (15)	0.0555 (9)	0.1306 (18)	0.0096 (10)	0.0164 (13)	−0.0239 (10)

Geometric parameters (Å, º)

C16—C17	1.3417 (16)	C3—C4	1.3424 (17)
C16—C15	1.5061 (15)	C3—C2	1.5052 (18)
C16—C24	1.4823 (17)	C3—C11	1.4854 (18)
C14—O4	1.2201 (14)	O1—C1	1.2132 (16)
C14—O5	1.2981 (13)	O2—H2	0.8200
C14—C15	1.4984 (15)	O2—C1	1.3056 (15)
C17—H17	0.9300	C4—H4	0.9300
C17—C18	1.4639 (17)	C4—C5	1.4651 (17)
O5—H5	0.8200	C5—C10	1.3931 (18)
O6—C24	1.2215 (15)	C5—C6	1.3890 (19)
C15—H15A	0.9700	O3—C11	1.2166 (16)
C15—H15B	0.9700	C2—H2A	0.9700
C18—C19	1.3943 (17)	C2—H2B	0.9700
C18—C23	1.3960 (17)	C2—C1	1.5012 (18)
C24—C25	1.4995 (18)	C11—C12	1.501 (2)
C19—H19	0.9300	C10—H10	0.9300
C19—C20	1.381 (2)	C10—C9	1.380 (2)
C23—H23	0.9300	C9—H9	0.9300
C23—C22	1.386 (2)	C9—C8	1.367 (2)
C25—H25A	0.9600	C6—H6	0.9300
C25—H25B	0.9600	C6—C7	1.382 (2)
C25—H25C	0.9600	C8—C7	1.378 (2)
C22—H22	0.9300	C8—C13	1.511 (2)
C22—C21	1.381 (2)	C7—H7	0.9300
C21—C20	1.379 (2)	C12—H12A	0.9600
C21—C26	1.508 (2)	C12—H12B	0.9600
C20—H20	0.9300	C12—H12C	0.9600
C26—H26A	0.9600	C13—H13A	0.9600
C26—H26B	0.9600	C13—H13B	0.9600
C26—H26C	0.9600	C13—H13C	0.9600
C17—C16—C15	124.87 (11)	C4—C3—C2	125.67 (12)
C17—C16—C24	120.97 (10)	C4—C3—C11	120.59 (12)
C24—C16—C15	114.16 (10)	C11—C3—C2	113.69 (11)
O4—C14—O5	122.88 (10)	C1—O2—H2	109.5
O4—C14—C15	123.19 (10)	C3—C4—H4	115.1
O5—C14—C15	113.93 (10)	C3—C4—C5	129.83 (12)
C16—C17—H17	115.3	C5—C4—H4	115.1
C16—C17—C18	129.44 (11)	C10—C5—C4	117.89 (12)
C18—C17—H17	115.3	C6—C5—C4	124.78 (11)
C14—O5—H5	109.5	C6—C5—C10	117.29 (13)
C16—C15—H15A	108.9	C3—C2—H2A	108.7
C16—C15—H15B	108.9	C3—C2—H2B	108.7
C14—C15—C16	113.50 (9)	H2A—C2—H2B	107.6
C14—C15—H15A	108.9	C1—C2—C3	114.24 (11)
C14—C15—H15B	108.9	C1—C2—H2A	108.7
H15A—C15—H15B	107.7	C1—C2—H2B	108.7
C19—C18—C17	124.22 (11)	O1—C1—O2	123.04 (12)
C19—C18—C23	117.17 (12)	O1—C1—C2	123.22 (11)
C23—C18—C17	118.48 (11)	O2—C1—C2	113.64 (12)
C16—C24—C25	120.56 (11)	C3—C11—C12	120.61 (12)
O6—C24—C16	119.23 (11)	O3—C11—C3	119.53 (13)
O6—C24—C25	120.20 (12)	O3—C11—C12	119.85 (13)
C18—C19—H19	119.4	C5—C10—H10	119.6
C20—C19—C18	121.16 (13)	C9—C10—C5	120.71 (14)
C20—C19—H19	119.4	C9—C10—H10	119.6
C18—C23—H23	119.6	C10—C9—H9	119.0
C22—C23—C18	120.77 (13)	C8—C9—C10	121.94 (14)
C22—C23—H23	119.6	C8—C9—H9	119.0
C24—C25—H25A	109.5	C5—C6—H6	119.6
C24—C25—H25B	109.5	C7—C6—C5	120.82 (14)
C24—C25—H25C	109.5	C7—C6—H6	119.6
H25A—C25—H25B	109.5	C9—C8—C7	117.62 (14)
H25A—C25—H25C	109.5	C9—C8—C13	121.87 (16)
H25B—C25—H25C	109.5	C7—C8—C13	120.51 (17)
C23—C22—H22	119.2	C6—C7—H7	119.2
C21—C22—C23	121.50 (13)	C8—C7—C6	121.57 (15)
C21—C22—H22	119.2	C8—C7—H7	119.2
C22—C21—C26	121.71 (16)	C11—C12—H12A	109.5
C20—C21—C22	117.79 (13)	C11—C12—H12B	109.5
C20—C21—C26	120.49 (16)	C11—C12—H12C	109.5
C19—C20—H20	119.3	H12A—C12—H12B	109.5
C21—C20—C19	121.42 (14)	H12A—C12—H12C	109.5
C21—C20—H20	119.3	H12B—C12—H12C	109.5
C21—C26—H26A	109.5	C8—C13—H13A	109.5
C21—C26—H26B	109.5	C8—C13—H13B	109.5
C21—C26—H26C	109.5	C8—C13—H13C	109.5
H26A—C26—H26B	109.5	H13A—C13—H13B	109.5
H26A—C26—H26C	109.5	H13A—C13—H13C	109.5
H26B—C26—H26C	109.5	H13B—C13—H13C	109.5
C16—C17—C18—C19	−31.0 (2)	C3—C4—C5—C10	−148.97 (15)
C16—C17—C18—C23	153.27 (13)	C3—C4—C5—C6	33.5 (2)
O4—C14—C15—C16	−5.22 (17)	C3—C2—C1—O1	28.9 (2)
C17—C16—C15—C14	101.54 (13)	C3—C2—C1—O2	−154.42 (12)
C17—C16—C24—O6	−178.25 (12)	C4—C3—C2—C1	−101.98 (15)
C17—C16—C24—C25	1.01 (17)	C4—C3—C11—O3	173.44 (14)
C17—C18—C19—C20	−179.59 (14)	C4—C3—C11—C12	−5.2 (2)
C17—C18—C23—C22	−179.83 (12)	C4—C5—C10—C9	179.70 (15)
O5—C14—C15—C16	174.08 (10)	C4—C5—C6—C7	179.85 (16)
C15—C16—C17—C18	−5.48 (19)	C5—C10—C9—C8	1.4 (3)
C15—C16—C24—O6	2.48 (16)	C5—C6—C7—C8	−0.9 (3)
C15—C16—C24—C25	−178.26 (11)	C2—C3—C4—C5	3.4 (2)
C18—C19—C20—C21	0.4 (2)	C2—C3—C11—O3	−9.04 (19)
C18—C23—C22—C21	−1.1 (2)	C2—C3—C11—C12	172.34 (15)
C24—C16—C17—C18	175.34 (11)	C11—C3—C4—C5	−179.38 (13)
C24—C16—C15—C14	−79.23 (12)	C11—C3—C2—C1	80.64 (15)
C19—C18—C23—C22	4.2 (2)	C10—C5—C6—C7	2.4 (3)
C23—C18—C19—C20	−3.8 (2)	C10—C9—C8—C7	0.2 (3)
C23—C22—C21—C20	−2.4 (2)	C10—C9—C8—C13	179.10 (18)
C23—C22—C21—C26	178.96 (15)	C9—C8—C7—C6	−0.4 (3)
C22—C21—C20—C19	2.8 (2)	C6—C5—C10—C9	−2.6 (2)
C26—C21—C20—C19	−178.59 (16)	C13—C8—C7—C6	−179.39 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4^i	0.82	1.82	2.6310 (12)	171
O2—H2···O1^ii	0.82	1.85	2.6714 (15)	177

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