organic compounds
6-[(4′-Ethoxycarbonyl-[1,1′-biphenyl]-4-yl)oxy]hexanoic acid
aFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Puebla, Pue, Mexico, and bCentro de Química, ICUAP, Benemérita Universidad Autónoma de Puebla, Puebla, Pue, Mexico
*Correspondence e-mail: angel.mendoza@correo.buap.mx
In the title compound, C21H24O5, the dihedral angle between the benzene rings is 19.57 (15)°. In the crystal, the molecular arrangement makes up head-to-head centrosymmetric dimers assembled by pairs of O—H⋯O bonds; this arrangement builds a graph-set ring motif of R22(8). The dimers are linked into a tape running along the b-axis direction through C—H⋯O interactions. The packing is further consolidated by C—H⋯π interactions, forming layers parallel to (10-2).
CCDC reference: 962005
Related literature
For hydrogen-bonding assemblies, see: Braga et al. (2004). For hydrogen-bonding packing modes and applications of hydrogen bonds, see: Jeong et al. (2006); Leiserowitz (1976). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).
Experimental
Crystal data
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Data collection: XSCANS (Siemens, 1994); cell XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
CCDC reference: 962005
10.1107/S1600536813025877/is5302sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813025877/is5302Isup2.hkl
6.2 g (14 mmol) of benzyl 6-(ethyl 4'-oxydiphenyl-4-carboxylate)-hexanoate was added to 90 ml of dry ethyl acetate. 5% Pd—C (0.029 g) was then added with stirring. The hydrogenolisis was allowed to proceed for 8.5 h under hydrogen atmosphere at room temperature. After the removal of the catalyst by filtration and evaporation of the ethyl acetate under reduced pressure, the residue was then dissolved in hot methylene chloride and the solution was allowed to cool to -10 °C. It gave a white crystalline solid which was filtered off (4.8 g, 13.48 mmol, yield 97%). Crystals of I were grown from a solution of acetone by slow evaporation technique at room temperature. Anal. Calc. for C21H24O5: C 70.79, H 6.74%. Found: C 70.86, H 6.92%. IR(solid state, cm-1): ν (C—HAr) 3028; ν (C—HAliph) 2938; ν (C= O, Aliph.) 1703; ν (C=O, COOH) 1694; ν (C=C, Ar) 1600. 1H NMR [400 MHz; CDCl3, (CH3)4Si) δ (p.p.m.)]: 1.40 (t, 3H21, CH3), 1.55 (m, 2H4, CH2), 1.74 (m, 2H3, CH2), 1.84 (m, 2H5, CH2), 2.41 (t, 2H2, CH2—COOH), 4.01 (t, 2H6, O—CH2), 4.38 (q, 2H20 Me—CH2—O), 6.98 (d, 2H), 7.55 (d, 2H), 7.62 (d, 2H), 8.07 (d, 2H). 13C NMR [100 MHz; CDCl3, (CH3)4Si δ (p.p.m.)]: C21 14.61, C4 24.64, C3 25.82, C5, 29.15, C2 34.05, C20 61.15, C6 67.93, C12 and C8 115.11, C15 and C17 126.63, C14 and C18 128.57, C9 and C11 130.29, C10 132.57, C16 145.36, C13 145.36, C7 159.48, C19 166.87, C1 179.41.
H atoms linked to C and O atoms were placed in geometrical idealized positions (C—H = 0.93–0.97 Å and O—H = 0.82 Å) and refined as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(Cmethyl, O).
Data collection: XSCANS (Siemens, 1994); cell
XSCANS (Siemens, 1994); data reduction: XSCANS (Siemens, 1994); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. A view of the centrosymmetric dimer of the title compound. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. A crystal packing view of the title compound. Displacement ellipsoids are drawn at the 50% probability level. |
C21H24O5 | F(000) = 760 |
Mr = 356.4 | Dx = 1.243 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 43 reflections |
a = 9.111 (2) Å | θ = 9.1–33.6° |
b = 14.753 (3) Å | µ = 0.09 mm−1 |
c = 14.427 (2) Å | T = 298 K |
β = 100.785 (14)° | PRISM, colorless |
V = 1904.9 (6) Å3 | 0.5 × 0.5 × 0.4 mm |
Z = 4 |
Siemens P4 diffractometer | Rint = 0.031 |
Graphite monochromator | θmax = 24.7°, θmin = 2.0° |
ω scans | h = −1→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −17→1 |
Tmin = 0.891, Tmax = 0.911 | l = −16→16 |
4265 measured reflections | 3 standard reflections every 97 reflections |
3217 independent reflections | intensity decay: 6% |
1628 reflections with I > 2σ(I) |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.059 | w = 1/[σ2(Fo2) + (0.0433P)2 + 0.9974P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.171 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.16 e Å−3 |
3217 reflections | Δρmin = −0.15 e Å−3 |
238 parameters | Extinction correction: SHELXL |
0 restraints | Extinction coefficient: 0.0013 (4) |
Primary atom site location: structure-invariant direct methods |
C21H24O5 | V = 1904.9 (6) Å3 |
Mr = 356.4 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.111 (2) Å | µ = 0.09 mm−1 |
b = 14.753 (3) Å | T = 298 K |
c = 14.427 (2) Å | 0.5 × 0.5 × 0.4 mm |
β = 100.785 (14)° |
Siemens P4 diffractometer | 1628 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.031 |
Tmin = 0.891, Tmax = 0.911 | 3 standard reflections every 97 reflections |
4265 measured reflections | intensity decay: 6% |
3217 independent reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.16 e Å−3 |
3217 reflections | Δρmin = −0.15 e Å−3 |
238 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8791 (4) | −0.8969 (2) | 0.4560 (2) | 0.0645 (9) | |
C2 | 0.7761 (4) | −0.82076 (19) | 0.4252 (2) | 0.0672 (9) | |
H2A | 0.6847 | −0.8309 | 0.4491 | 0.081* | |
H2B | 0.7504 | −0.8216 | 0.3569 | 0.081* | |
C3 | 0.8346 (4) | −0.72759 (19) | 0.4559 (3) | 0.0712 (10) | |
H3A | 0.9243 | −0.7157 | 0.4309 | 0.085* | |
H3B | 0.8608 | −0.7256 | 0.5242 | 0.085* | |
C4 | 0.7197 (4) | −0.65502 (19) | 0.4220 (2) | 0.0721 (10) | |
H4A | 0.6936 | −0.6578 | 0.3538 | 0.087* | |
H4B | 0.6301 | −0.6678 | 0.4469 | 0.087* | |
C5 | 0.7716 (4) | −0.5605 (2) | 0.4506 (3) | 0.0790 (11) | |
H5A | 0.8617 | −0.5473 | 0.4265 | 0.095* | |
H5B | 0.7956 | −0.5568 | 0.5189 | 0.095* | |
C6 | 0.6529 (4) | −0.4906 (2) | 0.4133 (3) | 0.0748 (10) | |
H6A | 0.6288 | −0.4933 | 0.345 | 0.09* | |
H6B | 0.5626 | −0.5026 | 0.4378 | 0.09* | |
C7 | 0.6196 (4) | −0.3305 (2) | 0.4188 (2) | 0.0666 (9) | |
C8 | 0.4757 (4) | −0.3335 (2) | 0.3664 (2) | 0.0688 (9) | |
H8 | 0.4334 | −0.3885 | 0.3442 | 0.083* | |
C9 | 0.3949 (4) | −0.2531 (2) | 0.3471 (2) | 0.0639 (9) | |
H9 | 0.2982 | −0.2558 | 0.3121 | 0.077* | |
C10 | 0.4537 (3) | −0.16963 (19) | 0.3782 (2) | 0.0550 (8) | |
C11 | 0.5982 (4) | −0.1695 (2) | 0.4320 (2) | 0.0655 (9) | |
H11 | 0.6409 | −0.1148 | 0.4551 | 0.079* | |
C12 | 0.6788 (4) | −0.2480 (2) | 0.4516 (2) | 0.0706 (10) | |
H12 | 0.7747 | −0.2455 | 0.4876 | 0.085* | |
C13 | 0.3703 (3) | −0.08361 (19) | 0.3554 (2) | 0.0560 (8) | |
C14 | 0.2155 (4) | −0.0809 (2) | 0.3260 (2) | 0.0724 (10) | |
H14 | 0.1615 | −0.1347 | 0.3219 | 0.087* | |
C15 | 0.1407 (4) | −0.0002 (2) | 0.3031 (3) | 0.0750 (10) | |
H15 | 0.0375 | −0.0008 | 0.2835 | 0.09* | |
C16 | 0.2158 (3) | 0.0809 (2) | 0.3086 (2) | 0.0598 (8) | |
C17 | 0.3689 (4) | 0.0802 (2) | 0.3380 (2) | 0.0657 (9) | |
H17 | 0.4218 | 0.1345 | 0.3424 | 0.079* | |
C18 | 0.4447 (3) | −0.0007 (2) | 0.3611 (2) | 0.0631 (9) | |
H18 | 0.5479 | 0.0004 | 0.3809 | 0.076* | |
C19 | 0.1335 (4) | 0.1663 (2) | 0.2828 (2) | 0.0699 (9) | |
C20 | 0.1574 (4) | 0.3263 (2) | 0.2690 (3) | 0.0835 (11) | |
H20A | 0.0745 | 0.3366 | 0.3012 | 0.1* | |
H20B | 0.1206 | 0.3301 | 0.2016 | 0.1* | |
C21 | 0.2767 (4) | 0.3949 (2) | 0.2988 (3) | 0.0951 (13) | |
H21A | 0.3595 | 0.3827 | 0.2681 | 0.143* | |
H21B | 0.3095 | 0.392 | 0.366 | 0.143* | |
H21C | 0.2381 | 0.4544 | 0.2815 | 0.143* | |
O1 | 0.8276 (3) | −0.97632 (15) | 0.42837 (19) | 0.0836 (8) | |
H1 | 0.8874 | −1.0153 | 0.4517 | 0.125* | |
O2 | 1.0048 (3) | −0.88595 (14) | 0.50571 (18) | 0.0784 (7) | |
O3 | 0.7090 (3) | −0.40416 (14) | 0.44254 (17) | 0.0856 (8) | |
O4 | −0.0006 (3) | 0.17132 (17) | 0.2554 (2) | 0.1023 (9) | |
O5 | 0.2228 (2) | 0.23813 (15) | 0.29348 (17) | 0.0774 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.060 (2) | 0.0473 (19) | 0.085 (2) | 0.0006 (17) | 0.0096 (18) | 0.0006 (18) |
C2 | 0.068 (2) | 0.0511 (18) | 0.081 (2) | 0.0086 (17) | 0.0084 (18) | 0.0084 (17) |
C3 | 0.071 (2) | 0.0500 (19) | 0.093 (3) | 0.0087 (17) | 0.0146 (19) | 0.0075 (18) |
C4 | 0.085 (2) | 0.0500 (19) | 0.079 (2) | 0.0125 (18) | 0.0099 (19) | 0.0045 (17) |
C5 | 0.095 (3) | 0.0496 (19) | 0.089 (3) | 0.0114 (19) | 0.010 (2) | 0.0040 (18) |
C6 | 0.090 (3) | 0.0483 (19) | 0.086 (3) | 0.0049 (18) | 0.014 (2) | 0.0031 (18) |
C7 | 0.074 (2) | 0.0485 (19) | 0.075 (2) | 0.0104 (18) | 0.0078 (18) | −0.0006 (17) |
C8 | 0.078 (2) | 0.0464 (18) | 0.079 (2) | 0.0005 (17) | 0.0067 (19) | −0.0051 (17) |
C9 | 0.0571 (19) | 0.0562 (19) | 0.075 (2) | 0.0030 (16) | 0.0026 (16) | −0.0032 (17) |
C10 | 0.0584 (19) | 0.0447 (17) | 0.0610 (19) | 0.0020 (15) | 0.0088 (15) | −0.0036 (14) |
C11 | 0.066 (2) | 0.0474 (18) | 0.078 (2) | 0.0013 (16) | 0.0001 (17) | −0.0009 (16) |
C12 | 0.064 (2) | 0.054 (2) | 0.086 (3) | 0.0002 (17) | −0.0035 (18) | 0.0006 (18) |
C13 | 0.0538 (19) | 0.0515 (18) | 0.062 (2) | 0.0040 (15) | 0.0105 (15) | −0.0023 (15) |
C14 | 0.056 (2) | 0.058 (2) | 0.102 (3) | −0.0038 (17) | 0.0136 (19) | −0.0019 (19) |
C15 | 0.0468 (19) | 0.068 (2) | 0.109 (3) | 0.0068 (18) | 0.0090 (19) | 0.000 (2) |
C16 | 0.0518 (19) | 0.0542 (19) | 0.073 (2) | 0.0053 (15) | 0.0115 (16) | −0.0018 (16) |
C17 | 0.057 (2) | 0.0541 (19) | 0.082 (2) | 0.0047 (16) | 0.0026 (17) | −0.0025 (17) |
C18 | 0.0499 (18) | 0.0530 (19) | 0.083 (2) | 0.0054 (16) | 0.0033 (16) | −0.0031 (17) |
C19 | 0.059 (2) | 0.066 (2) | 0.084 (3) | 0.0098 (19) | 0.0146 (19) | 0.0019 (19) |
C20 | 0.079 (2) | 0.061 (2) | 0.109 (3) | 0.019 (2) | 0.016 (2) | 0.017 (2) |
C21 | 0.099 (3) | 0.063 (2) | 0.118 (3) | 0.004 (2) | 0.008 (3) | 0.010 (2) |
O1 | 0.0658 (15) | 0.0533 (14) | 0.121 (2) | 0.0020 (12) | −0.0096 (14) | −0.0037 (14) |
O2 | 0.0587 (14) | 0.0538 (14) | 0.1133 (19) | 0.0005 (11) | −0.0082 (13) | −0.0025 (13) |
O3 | 0.0923 (18) | 0.0503 (13) | 0.1049 (19) | 0.0138 (13) | −0.0050 (15) | −0.0019 (13) |
O4 | 0.0565 (15) | 0.0853 (19) | 0.160 (3) | 0.0175 (14) | 0.0074 (16) | 0.0118 (18) |
O5 | 0.0668 (15) | 0.0565 (14) | 0.1050 (19) | 0.0122 (12) | 0.0063 (13) | 0.0084 (13) |
C1—O2 | 1.243 (4) | C10—C13 | 1.484 (4) |
C1—O1 | 1.296 (3) | C11—C12 | 1.371 (4) |
C1—C2 | 1.478 (4) | C11—H11 | 0.93 |
C2—C3 | 1.511 (4) | C12—H12 | 0.93 |
C2—H2A | 0.97 | C13—C18 | 1.393 (4) |
C2—H2B | 0.97 | C13—C14 | 1.395 (4) |
C3—C4 | 1.513 (4) | C14—C15 | 1.381 (4) |
C3—H3A | 0.97 | C14—H14 | 0.93 |
C3—H3B | 0.97 | C15—C16 | 1.373 (4) |
C4—C5 | 1.505 (4) | C15—H15 | 0.93 |
C4—H4A | 0.97 | C16—C17 | 1.380 (4) |
C4—H4B | 0.97 | C16—C19 | 1.478 (4) |
C5—C6 | 1.519 (4) | C17—C18 | 1.388 (4) |
C5—H5A | 0.97 | C17—H17 | 0.93 |
C5—H5B | 0.97 | C18—H18 | 0.93 |
C6—O3 | 1.408 (4) | C19—O4 | 1.214 (4) |
C6—H6A | 0.97 | C19—O5 | 1.327 (4) |
C6—H6B | 0.97 | C20—O5 | 1.446 (4) |
C7—O3 | 1.364 (3) | C20—C21 | 1.489 (5) |
C7—C12 | 1.378 (4) | C20—H20A | 0.97 |
C7—C8 | 1.386 (4) | C20—H20B | 0.97 |
C8—C9 | 1.396 (4) | C21—H21A | 0.96 |
C8—H8 | 0.93 | C21—H21B | 0.96 |
C9—C10 | 1.384 (4) | C21—H21C | 0.96 |
C9—H9 | 0.93 | O1—H1 | 0.82 |
C10—C11 | 1.398 (4) | ||
O2—C1—O1 | 122.4 (3) | C11—C10—C13 | 120.8 (3) |
O2—C1—C2 | 122.6 (3) | C12—C11—C10 | 121.7 (3) |
O1—C1—C2 | 114.9 (3) | C12—C11—H11 | 119.1 |
C1—C2—C3 | 115.7 (3) | C10—C11—H11 | 119.1 |
C1—C2—H2A | 108.3 | C11—C12—C7 | 120.9 (3) |
C3—C2—H2A | 108.3 | C11—C12—H12 | 119.5 |
C1—C2—H2B | 108.3 | C7—C12—H12 | 119.5 |
C3—C2—H2B | 108.3 | C18—C13—C14 | 116.5 (3) |
H2A—C2—H2B | 107.4 | C18—C13—C10 | 120.9 (3) |
C2—C3—C4 | 111.4 (3) | C14—C13—C10 | 122.6 (3) |
C2—C3—H3A | 109.4 | C15—C14—C13 | 121.6 (3) |
C4—C3—H3A | 109.4 | C15—C14—H14 | 119.2 |
C2—C3—H3B | 109.4 | C13—C14—H14 | 119.2 |
C4—C3—H3B | 109.4 | C16—C15—C14 | 121.3 (3) |
H3A—C3—H3B | 108 | C16—C15—H15 | 119.4 |
C5—C4—C3 | 113.9 (3) | C14—C15—H15 | 119.4 |
C5—C4—H4A | 108.8 | C15—C16—C17 | 118.4 (3) |
C3—C4—H4A | 108.8 | C15—C16—C19 | 120.3 (3) |
C5—C4—H4B | 108.8 | C17—C16—C19 | 121.3 (3) |
C3—C4—H4B | 108.8 | C16—C17—C18 | 120.6 (3) |
H4A—C4—H4B | 107.7 | C16—C17—H17 | 119.7 |
C4—C5—C6 | 111.5 (3) | C18—C17—H17 | 119.7 |
C4—C5—H5A | 109.3 | C17—C18—C13 | 121.7 (3) |
C6—C5—H5A | 109.3 | C17—C18—H18 | 119.1 |
C4—C5—H5B | 109.3 | C13—C18—H18 | 119.1 |
C6—C5—H5B | 109.3 | O4—C19—O5 | 123.2 (3) |
H5A—C5—H5B | 108 | O4—C19—C16 | 124.5 (3) |
O3—C6—C5 | 108.3 (3) | O5—C19—C16 | 112.4 (3) |
O3—C6—H6A | 110 | O5—C20—C21 | 107.2 (3) |
C5—C6—H6A | 110 | O5—C20—H20A | 110.3 |
O3—C6—H6B | 110 | C21—C20—H20A | 110.3 |
C5—C6—H6B | 110 | O5—C20—H20B | 110.3 |
H6A—C6—H6B | 108.4 | C21—C20—H20B | 110.3 |
O3—C7—C12 | 116.1 (3) | H20A—C20—H20B | 108.5 |
O3—C7—C8 | 124.8 (3) | C20—C21—H21A | 109.5 |
C12—C7—C8 | 119.0 (3) | C20—C21—H21B | 109.5 |
C7—C8—C9 | 119.4 (3) | H21A—C21—H21B | 109.5 |
C7—C8—H8 | 120.3 | C20—C21—H21C | 109.5 |
C9—C8—H8 | 120.3 | H21A—C21—H21C | 109.5 |
C10—C9—C8 | 122.2 (3) | H21B—C21—H21C | 109.5 |
C10—C9—H9 | 118.9 | C1—O1—H1 | 109.5 |
C8—C9—H9 | 118.9 | C7—O3—C6 | 118.7 (3) |
C9—C10—C11 | 116.6 (3) | C19—O5—C20 | 118.3 (3) |
C9—C10—C13 | 122.5 (3) | ||
O2—C1—C2—C3 | 1.4 (5) | C18—C13—C14—C15 | 0.6 (5) |
O1—C1—C2—C3 | −179.4 (3) | C10—C13—C14—C15 | −178.5 (3) |
C1—C2—C3—C4 | −179.1 (3) | C13—C14—C15—C16 | −0.3 (6) |
C2—C3—C4—C5 | 179.9 (3) | C14—C15—C16—C17 | −0.1 (5) |
C3—C4—C5—C6 | 179.1 (3) | C14—C15—C16—C19 | 179.4 (3) |
C4—C5—C6—O3 | −179.9 (3) | C15—C16—C17—C18 | 0.2 (5) |
O3—C7—C8—C9 | 179.7 (3) | C19—C16—C17—C18 | −179.3 (3) |
C12—C7—C8—C9 | 0.7 (5) | C16—C17—C18—C13 | 0.2 (5) |
C7—C8—C9—C10 | 0.3 (5) | C14—C13—C18—C17 | −0.5 (5) |
C8—C9—C10—C11 | −1.2 (5) | C10—C13—C18—C17 | 178.6 (3) |
C8—C9—C10—C13 | 178.0 (3) | C15—C16—C19—O4 | −0.4 (6) |
C9—C10—C11—C12 | 1.1 (5) | C17—C16—C19—O4 | 179.1 (4) |
C13—C10—C11—C12 | −178.1 (3) | C15—C16—C19—O5 | 179.1 (3) |
C10—C11—C12—C7 | −0.1 (5) | C17—C16—C19—O5 | −1.4 (5) |
O3—C7—C12—C11 | −179.9 (3) | C12—C7—O3—C6 | 178.2 (3) |
C8—C7—C12—C11 | −0.9 (5) | C8—C7—O3—C6 | −0.8 (5) |
C9—C10—C13—C18 | −159.7 (3) | C5—C6—O3—C7 | −178.5 (3) |
C11—C10—C13—C18 | 19.4 (5) | O4—C19—O5—C20 | −1.6 (5) |
C9—C10—C13—C14 | 19.3 (5) | C16—C19—O5—C20 | 178.9 (3) |
C11—C10—C13—C14 | −161.5 (3) | C21—C20—O5—C19 | 173.0 (3) |
Cg1 is the centroid of the C13–C18 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.80 | 2.612 (3) | 170 |
C18—H18···O1ii | 0.93 | 2.54 | 3.460 (4) | 173 |
C6—H6A···Cg1iii | 0.97 | 2.78 | 3.668 (4) | 152 |
Symmetry codes: (i) −x+2, −y−2, −z+1; (ii) x, y+1, z; (iii) −x+1, y−1/2, −z+1/2. |
Cg1 is the centroid of the C13–C18 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.80 | 2.612 (3) | 170 |
C18—H18···O1ii | 0.93 | 2.54 | 3.460 (4) | 173 |
C6—H6A···Cg1iii | 0.97 | 2.78 | 3.668 (4) | 152 |
Symmetry codes: (i) −x+2, −y−2, −z+1; (ii) x, y+1, z; (iii) −x+1, y−1/2, −z+1/2. |
Acknowledgements
The authors acknowledge financial support from the VIEP–BUAP Project (LOVD-NAT12–1), PIFI-2012, Programa Anual de Cooperación Académica BUAP–UNAM 2012 and thank A. R. Hernández-Sosa for the crystal preparation.
References
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Hydrogen bonds are the strongest of the non-covalent interactions and have a high degree of directionality. Therefore, the design of molecules with hydrogen bonding capabilities is very important due to its numerous potential application (Braga et al., 2004) in nanotechnology, in crystal engineering, in template synthesis of polymers and networks, as well as in templated processes in biology such as the replication and transcription of nucleic acids. It has long been known that monocarboxylic acid may be interlinked to form the cyclic hydrogen-bonded dimer. This kind of molecular dimer, is well known as supramolecular synthon in crystals of carboxylic acids (Jeong et al., 2006; Leiserowitz et al., 1976). It is also important to point out that the title compound I contains a polymerizable end-group. Therefore it is a precursor for polymeric materials.
In the title compound, the ASU shows a molecule with two non-coplanar phenyl rings bonded by C10 and C13, both rings with p-substitution. The dihedral angle between these planes is 19.57 (15)°. On the other hand, C2 to C6 show an aliphatic extended-chain probably due to intermolecular interactions. The crystal packing makes up a head to head dimer assembled by intermolecular O—H···O bonds between the carboxyl groups (Fig. 1). This arrangement builds a graph-set ring R22(8) (Etter et al., 1990; Bernstein et al., 1995). Two more interactions C—H···O and C—H···π interactions, are identified, which stabilize the crystal packing. A tape of molecules from the C18—H18···O1 interaction is formed along the b axis. The C6—H6A···Cg1 interaction is building a layer of molecules parallel to (1 0 2). (Table 1; Cg1 is the centroid of the ring composed of C13–C18.)