Prop-2-ynyl 3-(3,4-di­hydroxy­phenyl)­prop-2-enoate monohydrate

Crystals of the title compound, C₁₂H₁₀O₄·H₂O, were obtained from the Knoevenagel condensation reaction of 3,4-di­hydroxy­benz­aldehyde and monoprop-2-ynyl malonate. The almost planar mol­ecule is the E isomer. There are intermolecular O—H...O and C—H...O hydrogen bonds and π–π interactions, which contribute to the formation of the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.101
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD (McArdle, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: SHELXL97.

Prop-2-ynyl 3-(3,4-dihydroxyphenyl)prop-2-enoate monohydrate

Crystal data

C12H10O4·H2O	F(000) = 496
Mr = 236.22	Dx = 1.354 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 12.857 (3) Å	θ = 10.0–13.7°
b = 7.0660 (12) Å	µ = 0.11 mm^−1
c = 13.5410 (12) Å	T = 296 K
β = 109.560 (17)°	Prismatic, light brown
V = 1159.2 (4) Å^3	0.50 × 0.40 × 0.30 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	1461 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 25.2°, θmin = 1.9°
ω/2θ scans	h = −1→15
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	k = 0→8
Tmin = 0.939, Tmax = 0.969	l = −16→15
2387 measured reflections	3 standard reflections every 60 min
2087 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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0424P)^2 + 0.3495P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2087 reflections	Δρmax = 0.16 e Å^−3
165 parameters	Δρmin = −0.13 e Å^−3
3 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: 0.0107 (18)

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	0.41818 (9)	0.1022 (2)	0.53731 (9)	0.0528 (4)
H1	0.4689	0.0917	0.5942	0.079*
O2	0.24284 (10)	0.1685 (2)	0.36780 (9)	0.0537 (4)
H2	0.3042	0.1241	0.3729	0.081*
O3	−0.19029 (10)	0.3271 (2)	0.62331 (9)	0.0567 (4)
O4	−0.27663 (9)	0.33990 (18)	0.45120 (9)	0.0446 (3)
O5	0.60599 (12)	0.0572 (2)	0.70384 (11)	0.0620 (4)
H5B	0.613 (2)	−0.029 (3)	0.7492 (17)	0.122 (12)*
H5A	0.644 (2)	0.156 (3)	0.726 (2)	0.132 (13)*
C1	0.20739 (14)	0.1883 (3)	0.65915 (14)	0.0522 (5)
H1A	0.1996	0.1927	0.7249	0.063*
C2	0.30950 (14)	0.1481 (3)	0.65144 (14)	0.0525 (5)
H2A	0.3696	0.1261	0.7117	0.063*
C3	0.32248 (13)	0.1406 (2)	0.55474 (13)	0.0413 (4)
C4	0.23154 (13)	0.1737 (2)	0.46495 (12)	0.0389 (4)
C5	0.13060 (13)	0.2139 (2)	0.47295 (13)	0.0401 (4)
H5	0.0707	0.2360	0.4125	0.048*
C6	0.11623 (13)	0.2224 (2)	0.57076 (13)	0.0413 (4)
C7	0.00984 (13)	0.2605 (2)	0.58237 (14)	0.0442 (4)
H7	0.0099	0.2687	0.6509	0.053*
C8	−0.08740 (13)	0.2851 (3)	0.50828 (14)	0.0447 (4)
H8	−0.0925	0.2810	0.4382	0.054*
C9	−0.18623 (13)	0.3186 (2)	0.53536 (13)	0.0402 (4)
C10	−0.37615 (13)	0.3756 (3)	0.47547 (13)	0.0456 (4)
H10A	−0.3655	0.4842	0.5216	0.055*
H10B	−0.3933	0.2669	0.5109	0.055*
C11	−0.46607 (15)	0.4115 (3)	0.37898 (14)	0.0474 (5)
C12	−0.54253 (17)	0.4427 (3)	0.30519 (16)	0.0626 (6)
H12	−0.6036	0.4676	0.2462	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0337 (6)	0.0756 (10)	0.0463 (7)	0.0098 (6)	0.0098 (5)	−0.0016 (7)
O2	0.0397 (7)	0.0804 (10)	0.0412 (7)	0.0118 (7)	0.0138 (5)	−0.0002 (6)
O3	0.0475 (7)	0.0825 (10)	0.0409 (7)	0.0088 (7)	0.0160 (6)	0.0028 (7)
O4	0.0356 (6)	0.0586 (8)	0.0405 (6)	0.0033 (6)	0.0139 (5)	−0.0032 (6)
O5	0.0586 (9)	0.0644 (10)	0.0510 (8)	0.0007 (8)	0.0025 (7)	0.0003 (8)
C1	0.0474 (10)	0.0698 (13)	0.0404 (9)	0.0065 (10)	0.0160 (8)	0.0046 (9)
C2	0.0398 (9)	0.0705 (14)	0.0413 (10)	0.0082 (9)	0.0059 (8)	0.0036 (9)
C3	0.0336 (8)	0.0420 (10)	0.0463 (9)	0.0023 (7)	0.0110 (7)	−0.0004 (8)
C4	0.0392 (9)	0.0377 (9)	0.0394 (8)	0.0004 (8)	0.0125 (7)	−0.0006 (8)
C5	0.0335 (8)	0.0418 (10)	0.0418 (9)	0.0019 (7)	0.0082 (7)	0.0014 (7)
C6	0.0384 (9)	0.0397 (10)	0.0468 (9)	0.0013 (8)	0.0157 (8)	0.0022 (8)
C7	0.0436 (10)	0.0446 (10)	0.0481 (10)	0.0005 (8)	0.0201 (8)	0.0025 (8)
C8	0.0425 (9)	0.0474 (11)	0.0475 (10)	0.0020 (8)	0.0195 (8)	0.0018 (8)
C9	0.0400 (9)	0.0378 (9)	0.0428 (9)	0.0002 (7)	0.0139 (7)	0.0002 (7)
C10	0.0365 (9)	0.0564 (12)	0.0456 (10)	0.0014 (8)	0.0163 (8)	−0.0019 (8)
C11	0.0408 (9)	0.0530 (11)	0.0498 (10)	0.0010 (8)	0.0170 (9)	−0.0079 (9)
C12	0.0486 (11)	0.0767 (15)	0.0552 (12)	0.0074 (11)	0.0076 (10)	−0.0088 (11)

Geometric parameters (Å, º)

O1—C3	1.356 (2)	C3—C4	1.396 (2)
O1—H1	0.8299	C4—C5	1.368 (2)
O2—C4	1.372 (2)	C5—C6	1.398 (2)
O2—H2	0.8299	C5—H5	0.9300
O3—C9	1.2108 (19)	C6—C7	1.453 (2)
O4—C9	1.336 (2)	C7—C8	1.327 (2)
O4—C10	1.446 (2)	C7—H7	0.9300
O5—H5B	0.851 (10)	C8—C9	1.455 (2)
O5—H5A	0.847 (10)	C8—H8	0.9300
C1—C2	1.381 (2)	C10—C11	1.448 (2)
C1—C6	1.387 (2)	C10—H10A	0.9700
C1—H1A	0.9300	C10—H10B	0.9700
C2—C3	1.375 (2)	C11—C12	1.164 (3)
C2—H2A	0.9300	C12—H12	0.9300
C3—O1—H1	109.5	C1—C6—C7	119.51 (16)
C4—O2—H2	109.5	C5—C6—C7	122.54 (15)
C9—O4—C10	114.15 (13)	C8—C7—C6	128.70 (17)
H5B—O5—H5A	115 (2)	C8—C7—H7	115.6
C2—C1—C6	121.35 (16)	C6—C7—H7	115.6
C2—C1—H1A	119.3	C7—C8—C9	120.81 (17)
C6—C1—H1A	119.3	C7—C8—H8	119.6
C3—C2—C1	120.10 (16)	C9—C8—H8	119.6
C3—C2—H2A	120.0	O3—C9—O4	121.44 (15)
C1—C2—H2A	120.0	O3—C9—C8	125.79 (16)
O1—C3—C2	125.46 (15)	O4—C9—C8	112.77 (15)
O1—C3—C4	115.23 (15)	O4—C10—C11	109.00 (14)
C2—C3—C4	119.31 (15)	O4—C10—H10A	109.9
C5—C4—O2	119.31 (14)	C11—C10—H10A	109.9
C5—C4—C3	120.41 (15)	O4—C10—H10B	109.9
O2—C4—C3	120.28 (14)	C11—C10—H10B	109.9
C4—C5—C6	120.90 (15)	H10A—C10—H10B	108.3
C4—C5—H5	119.5	C12—C11—C10	175.7 (2)
C6—C5—H5	119.5	C11—C12—H12	180.0
C1—C6—C5	117.93 (15)
C6—C1—C2—C3	−0.2 (3)	C4—C5—C6—C1	−0.1 (3)
C1—C2—C3—O1	−179.85 (18)	C4—C5—C6—C7	−178.58 (16)
C1—C2—C3—C4	−0.1 (3)	C1—C6—C7—C8	−175.7 (2)
O1—C3—C4—C5	−179.97 (16)	C5—C6—C7—C8	2.8 (3)
C2—C3—C4—C5	0.2 (3)	C6—C7—C8—C9	178.76 (17)
O1—C3—C4—O2	−0.8 (2)	C10—O4—C9—O3	0.8 (2)
C2—C3—C4—O2	179.43 (17)	C10—O4—C9—C8	−179.31 (15)
O2—C4—C5—C6	−179.34 (16)	C7—C8—C9—O3	0.0 (3)
C3—C4—C5—C6	−0.1 (3)	C7—C8—C9—O4	−179.88 (17)
C2—C1—C6—C5	0.3 (3)	C9—O4—C10—C11	175.34 (15)
C2—C1—C6—C7	178.79 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5	0.83	1.90	2.7150 (19)	166
O2—H2···O5^i	0.83	2.20	2.920 (2)	145
O2—H2···O1	0.83	2.22	2.6655 (17)	114
O5—H5B···O3^ii	0.85 (1)	1.96 (2)	2.757 (2)	155 (3)
O5—H5A···O2^iii	0.85 (1)	2.28 (2)	3.028 (2)	148 (3)
C12—H12···O2^iv	0.93	2.40	3.260 (3)	154

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