Butyl 3-(3,4-dihydroxy­phen­yl)prop-2-enoate

The C=C double bond of the title compound, C₁₃H₁₆O₄, synthesized by the Knoevenagel-Doebner condensation, is in the E configuration. There are intra- and inter­molecular hydrogen bonds in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.068
• wR factor = 0.213
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O3     -   C9      ..      11.66 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C5     -   C6      ..       7.81 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C3      ..       6.83 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.32
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C13 H16 O4

   0 ALERT level A = In general: serious problem
   2 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1993); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Version 1.05; Farrugia, 1999); software used to prepare material for publication: SHELXL97.

Butyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

Crystal data

C13H16O4	Z = 2
Mr = 236.26	F(000) = 252
Triclinic, P1	Dx = 1.251 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.282 (5) Å	Cell parameters from 25 reflections
b = 10.490 (5) Å	θ = 9.8–13.7°
c = 11.558 (7) Å	µ = 0.09 mm^−1
α = 83.95 (6)°	T = 298 K
β = 84.31 (7)°	Prism, colourless
γ = 81.14 (6)°	0.50 × 0.40 × 0.30 mm
V = 627.0 (8) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	1301 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 25.2°, θmin = 1.8°
ω/2θ scans	h = −1→6
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.964, Tmax = 0.964	l = −13→13
3050 measured reflections	3 standard reflections every 60 min
2259 independent reflections	intensity decay: 0.3%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.068	H-atom parameters constrained
wR(F^2) = 0.213	w = 1/[σ^2(Fo^2) + (0.1452P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.004
2259 reflections	Δρmax = 0.31 e Å^−3
158 parameters	Δρmin = −0.33 e Å^−3
6 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (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	−0.15551 (12)	0.36945 (5)	0.48529 (5)	0.05835 (18)
H1	−0.2755	0.3569	0.4487	0.088*
O2	0.22669 (12)	0.37670 (5)	0.62553 (6)	0.0686 (2)
H2	0.1505	0.4362	0.5831	0.103*
O3	−0.49799 (13)	−0.29409 (6)	0.65183 (5)	0.0725 (2)
O4	−0.24918 (12)	−0.38693 (5)	0.78993 (5)	0.06073 (19)
C1	−0.19922 (17)	0.15206 (7)	0.56953 (7)	0.0471 (2)
H1A	−0.3309	0.1483	0.5228	0.056*
C2	−0.08758 (16)	0.26280 (7)	0.56066 (7)	0.0442 (2)
C3	0.10893 (17)	0.27001 (8)	0.63010 (8)	0.0490 (2)
C4	0.18835 (18)	0.16454 (9)	0.70642 (8)	0.0579 (3)
H4	0.3195	0.1686	0.7534	0.069*
C5	0.07701 (18)	0.05383 (8)	0.71408 (8)	0.0537 (3)
H5	0.1352	−0.0165	0.7654	0.064*
C6	−0.12127 (16)	0.04541 (7)	0.64627 (7)	0.0444 (2)
C7	−0.24616 (17)	−0.07016 (8)	0.65158 (7)	0.0493 (2)
H7	−0.3770	−0.0660	0.6025	0.059*
C8	−0.19545 (18)	−0.17953 (8)	0.71771 (7)	0.0532 (3)
H8	−0.0684	−0.1865	0.7692	0.064*
C9	−0.32881 (17)	−0.28948 (7)	0.71378 (7)	0.0485 (2)
C10	−0.37054 (19)	−0.50276 (8)	0.79766 (8)	0.0565 (3)
H10A	−0.3443	−0.5405	0.7235	0.068*
H10B	−0.5539	−0.4824	0.8180	0.068*
C11	−0.2466 (2)	−0.59535 (8)	0.89112 (8)	0.0578 (3)
H11A	−0.2628	−0.5535	0.9630	0.069*
H11B	−0.0649	−0.6173	0.8678	0.069*
C12	−0.3685 (2)	−0.71805 (9)	0.91283 (9)	0.0688 (3)
H12A	−0.5506	−0.6956	0.9351	0.083*
H12B	−0.3512	−0.7599	0.8409	0.083*
C13	−0.2487 (3)	−0.81213 (11)	1.00712 (10)	0.0958 (5)
H13A	−0.0686	−0.8352	0.9853	0.144*
H13B	−0.3306	−0.8886	1.0167	0.144*
H13C	−0.2709	−0.7724	1.0793	0.144*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0707 (3)	0.0378 (3)	0.0728 (3)	−0.0198 (3)	−0.0361 (3)	0.0114 (3)
O2	0.0791 (4)	0.0431 (3)	0.0934 (4)	−0.0264 (3)	−0.0428 (3)	0.0070 (3)
O3	0.0884 (4)	0.0545 (3)	0.0842 (4)	−0.0264 (3)	−0.0537 (3)	0.0156 (3)
O4	0.0828 (4)	0.0385 (3)	0.0671 (3)	−0.0198 (3)	−0.0371 (3)	0.0118 (3)
C1	0.0568 (5)	0.0388 (4)	0.0495 (4)	−0.0131 (4)	−0.0195 (4)	0.0005 (3)
C2	0.0483 (4)	0.0354 (4)	0.0506 (4)	−0.0073 (4)	−0.0148 (4)	−0.0003 (3)
C3	0.0507 (4)	0.0406 (4)	0.0599 (5)	−0.0118 (4)	−0.0173 (4)	−0.0054 (4)
C4	0.0601 (5)	0.0508 (5)	0.0690 (5)	−0.0154 (4)	−0.0335 (4)	0.0028 (4)
C5	0.0639 (5)	0.0398 (4)	0.0594 (5)	−0.0078 (4)	−0.0256 (4)	0.0051 (4)
C6	0.0519 (4)	0.0365 (4)	0.0468 (4)	−0.0077 (4)	−0.0153 (4)	−0.0013 (3)
C7	0.0576 (5)	0.0397 (4)	0.0549 (4)	−0.0119 (4)	−0.0230 (4)	−0.0005 (4)
C8	0.0620 (5)	0.0426 (4)	0.0596 (5)	−0.0139 (4)	−0.0262 (4)	0.0041 (4)
C9	0.0607 (5)	0.0379 (4)	0.0489 (4)	−0.0114 (4)	−0.0170 (4)	0.0038 (3)
C10	0.0750 (5)	0.0388 (4)	0.0607 (5)	−0.0164 (4)	−0.0257 (4)	0.0031 (4)
C11	0.0758 (6)	0.0417 (4)	0.0576 (5)	−0.0078 (4)	−0.0241 (4)	0.0032 (4)
C12	0.0887 (7)	0.0466 (5)	0.0735 (6)	−0.0159 (5)	−0.0265 (5)	0.0112 (4)
C13	0.1363 (10)	0.0589 (6)	0.0909 (7)	−0.0158 (7)	−0.0356 (7)	0.0253 (6)

Geometric parameters (Å, º)

O1—C2	1.3682 (13)	C7—C8	1.3166 (14)
O1—H1	0.8299	C7—H7	0.9300
O2—C3	1.3556 (13)	C8—C9	1.4478 (15)
O2—H2	0.8299	C8—H8	0.9300
O3—C9	1.2088 (15)	C10—C11	1.5039 (16)
O4—C9	1.3220 (13)	C10—H10A	0.9700
O4—C10	1.4495 (14)	C10—H10B	0.9700
C1—C2	1.3717 (14)	C11—C12	1.5129 (17)
C1—C6	1.3890 (14)	C11—H11A	0.9700
C1—H1A	0.9300	C11—H11B	0.9700
C2—C3	1.3890 (17)	C12—C13	1.5097 (19)
C3—C4	1.3794 (15)	C12—H12A	0.9700
C4—C5	1.3714 (15)	C12—H12B	0.9700
C4—H4	0.9300	C13—H13A	0.9599
C5—C6	1.3873 (17)	C13—H13B	0.9599
C5—H5	0.9300	C13—H13C	0.9599
C6—C7	1.4599 (15)
C2—O1—H1	109.5	O3—C9—O4	122.31 (9)
C3—O2—H2	109.5	O3—C9—C8	125.78 (9)
C9—O4—C10	117.97 (9)	O4—C9—C8	111.89 (9)
C2—C1—C6	121.92 (10)	O4—C10—C11	106.53 (9)
C2—C1—H1A	119.0	O4—C10—H10A	110.4
C6—C1—H1A	119.0	C11—C10—H10A	110.4
O1—C2—C1	123.97 (9)	O4—C10—H10B	110.4
O1—C2—C3	116.32 (9)	C11—C10—H10B	110.4
C1—C2—C3	119.70 (9)	H10A—C10—H10B	108.6
O2—C3—C4	118.60 (10)	C10—C11—C12	111.72 (10)
O2—C3—C2	122.52 (9)	C10—C11—H11A	109.3
C4—C3—C2	118.88 (9)	C12—C11—H11A	109.3
C5—C4—C3	121.04 (10)	C10—C11—H11B	109.3
C5—C4—H4	119.5	C12—C11—H11B	109.3
C3—C4—H4	119.5	H11A—C11—H11B	107.9
C4—C5—C6	120.87 (9)	C13—C12—C11	112.70 (11)
C4—C5—H5	119.6	C13—C12—H12A	109.1
C6—C5—H5	119.6	C11—C12—H12A	109.1
C5—C6—C1	117.59 (9)	C13—C12—H12B	109.1
C5—C6—C7	122.86 (9)	C11—C12—H12B	109.1
C1—C6—C7	119.54 (9)	H12A—C12—H12B	107.8
C8—C7—C6	127.65 (10)	C12—C13—H13A	109.5
C8—C7—H7	116.2	C12—C13—H13B	109.5
C6—C7—H7	116.2	H13A—C13—H13B	109.5
C7—C8—C9	122.88 (10)	C12—C13—H13C	109.5
C7—C8—H8	118.6	H13A—C13—H13C	109.5
C9—C8—H8	118.6	H13B—C13—H13C	109.5
C6—C1—C2—O1	179.07 (7)	C2—C1—C6—C7	−179.69 (8)
C6—C1—C2—C3	−0.16 (12)	C5—C6—C7—C8	0.10 (14)
O1—C2—C3—O2	0.78 (12)	C1—C6—C7—C8	179.26 (8)
C1—C2—C3—O2	−179.92 (8)	C6—C7—C8—C9	−178.59 (8)
O1—C2—C3—C4	−178.97 (7)	C10—O4—C9—O3	0.32 (12)
C1—C2—C3—C4	0.32 (12)	C10—O4—C9—C8	178.57 (7)
O2—C3—C4—C5	−179.58 (8)	C7—C8—C9—O3	−0.32 (14)
C2—C3—C4—C5	0.18 (13)	C7—C8—C9—O4	−178.50 (8)
C3—C4—C5—C6	−0.86 (14)	C9—O4—C10—C11	−179.19 (7)
C4—C5—C6—C1	0.99 (12)	O4—C10—C11—C12	176.60 (7)
C4—C5—C6—C7	−179.84 (8)	C10—C11—C12—C13	−179.51 (8)
C2—C1—C6—C5	−0.49 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^i	0.83	1.97	2.788 (3)	167
O2—H2···O1	0.83	2.29	2.726 (3)	113
O2—H2···O1^ii	0.83	2.11	2.818 (3)	143
C1—H1A···O3^i	0.93	2.55	3.255 (3)	133

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