organic compounds
3,5-Bis(benzyloxy)benzoic acid
aDepartamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, bPrograma de Ingenieria Agroindustrial, Universidad San Buenaventura, AA 7154, Santiago de Cali, Colombia, cCase Western Reserve University, Department of Macromolecular Science and Engineering, 2100 Adelbert Road, Kent Hale Smith Bldg, Cleveland, Ohio 44106, USA, and dInstituto de Física de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
*Correspondence e-mail: rodimo26@yahoo.es
In the title compound, C21H18O4, the outer benzyl rings are disordered over two resolved positions in a 0.50 ratio. The O—CH2 groups form dihedral angles of 4.1 (2) and 10.9 (4)° with the central benzene ring, adopting a syn–anti conformation with respect to this ring. In the crystal, the molecules are linked by O—H⋯O hydrogen bonds and weak C—H⋯O interactions, forming chains along [010].
Related literature
For properties of dendrimer chemistry, see: Fréchet (2002). For the diverse applications of 3,5-bis(benzyloxy)benzoic acid and its benzoate derivatives, see: Sivakumar et al. (2010); Remya et al. (2008); Hawker & Fréchet (1992). For magnetic and luminiscent properties of lanthanide benzoates, see: Busskamp et al. (2007). For the conformation of O—CH2 groups, see: Xiao et al. (2007). For related structures, see: Gainsford et al. (2009); Zhu et al. (2009). For graph-set motifs, see: Etter (1990). For hydrogen bonding, see: Nardelli (1995); Desiraju & Steiner (1999).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: COLLECT (Nonius, 2000); cell SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536812043796/hg5257sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812043796/hg5257Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812043796/hg5257Isup3.cml
Methyl 3,5-dihydroxybenzoate (2.0g, 12 mmol) was dissolved in 50 ml of acetonitrile and refluxed with potassium carbonate (8.0 g, 58 mmol) for 30 min. The resulting reaction mixture was refluxed at 68° C for 48 h following the addition of benzyl bromide (4.0 g, 24 mmol). The acetonitrile was evaporated off, and the residual mixture was poured into ice cold water. Methyl 3,5-bis-(benzyloxy)benzoate was obtained as a white precipitate. (2.0 g, 5.74 mmol), were taken from the precipitate, which was dissolved in 50 ml of ethanol. To this solution was added (1 g, 17.77 mmol) of KOH and it was placed under reflux. The reaction was followed by TLC until the presence of KOH was not longer observed. The reaction mixture was poured into ice cold water, acidified with dilute HCl, and the resulting precipitate was filtered, washed, dried, and recrystallized from ethanol. Yield, 1.67 g (89%). 3,5-Bis(benzyloxy)benzoic Acid, 1H-NMR (500 MHz) δ(p.p.m.), 7.45–7.46(d, 4H, J= 7 Hz), 7.39–7.41 (t, 4H, J=7 Hz), 7.32–7.35 (t, 2H, J= 7 Hz), 7.16(d, 2H, J= 2.5 Hz), 6.92–6.93 (t, 1H, J= 2.5 Hz), 5.15 (s, 4H). 13C-NMR: 166.88, 159.35, 136.64, 132.79, 138.45, 127.90, 127.63, 107.96, 106.50, 69.45. F T—IR (KBr): 3033 (Ar—H); 1690, 1159, 733, 698 cm-1.
All H-atoms were positioned geometrically using riding model with [C—H= 0.93 Å for aromatic, C—H= 0.82 Å for hydroxyl and C—H= 0.97 Å for methylene H atoms. Uiso(H)= 1.2Ueq(C) for aryl and methylene H atoms and 1.5Ueq(O) for hydroxyl H-atom]. During the
disordered sites around the two benzyl groups were found. Trial refinements were used with the split-atom approach for these extra sites with a constrained 50% occupancy each.Data collection: COLLECT (Nonius, 2000); cell
SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).C21H18O4 | Z = 2 |
Mr = 334.37 | F(000) = 352 |
Triclinic, P1 | Dx = 1.288 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.2801 (2) Å | Cell parameters from 3147 reflections |
b = 11.6830 (5) Å | θ = 2.9–26.4° |
c = 14.4803 (7) Å | µ = 0.09 mm−1 |
α = 83.303 (2)° | T = 295 K |
β = 80.775 (2)° | Block, colourless |
γ = 79.031 (1)° | 0.43 × 0.11 × 0.10 mm |
V = 862.17 (6) Å3 |
Nonius KappaCCD diffractometer | 1801 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 25.2°, θmin = 3.5° |
CCD rotation images, thick slices scans | h = −6→6 |
5626 measured reflections | k = −14→14 |
3084 independent reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.094P)2 + 0.0032P] where P = (Fo2 + 2Fc2)/3 |
3084 reflections | (Δ/σ)max < 0.001 |
316 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C21H18O4 | γ = 79.031 (1)° |
Mr = 334.37 | V = 862.17 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.2801 (2) Å | Mo Kα radiation |
b = 11.6830 (5) Å | µ = 0.09 mm−1 |
c = 14.4803 (7) Å | T = 295 K |
α = 83.303 (2)° | 0.43 × 0.11 × 0.10 mm |
β = 80.775 (2)° |
Nonius KappaCCD diffractometer | 1801 reflections with I > 2σ(I) |
5626 measured reflections | Rint = 0.036 |
3084 independent reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.15 e Å−3 |
3084 reflections | Δρmin = −0.15 e Å−3 |
316 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. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.2556 (3) | 0.46372 (17) | 0.58387 (13) | 0.0623 (5) | |
C2 | 0.4505 (3) | 0.43437 (15) | 0.65014 (12) | 0.0597 (5) | |
C3 | 0.4690 (3) | 0.51344 (17) | 0.71085 (12) | 0.0644 (5) | |
H3 | 0.3589 | 0.5858 | 0.7109 | 0.077* | |
C4 | 0.6534 (3) | 0.48473 (16) | 0.77226 (12) | 0.0639 (5) | |
C5 | 0.8181 (4) | 0.37791 (17) | 0.77144 (13) | 0.0673 (5) | |
H5 | 0.9413 | 0.3585 | 0.8125 | 0.081* | |
C6 | 0.7989 (4) | 0.29977 (17) | 0.70920 (14) | 0.0690 (5) | |
C7 | 0.6163 (3) | 0.32636 (17) | 0.64802 (13) | 0.0690 (5) | |
H7 | 0.6042 | 0.2734 | 0.6064 | 0.083* | |
C8 | 0.8524 (4) | 0.55033 (19) | 0.88979 (15) | 0.0773 (6) | |
H8A | 1.0236 | 0.5321 | 0.8534 | 0.093* | |
H8B | 0.8282 | 0.4854 | 0.9366 | 0.093* | |
C9 | 0.8300 (5) | 0.65976 (19) | 0.93627 (17) | 0.0705 (6) | 0.50 |
C11 | 0.592 (6) | 0.802 (3) | 1.0445 (16) | 0.132 (8) | 0.50 |
H11 | 0.4429 | 0.8290 | 1.0849 | 0.159* | 0.50 |
C10 | 0.626 (5) | 0.699 (2) | 0.9975 (15) | 0.112 (6) | 0.50 |
H10 | 0.4933 | 0.6553 | 1.0109 | 0.134* | 0.50 |
C12 | 0.798 (6) | 0.854 (3) | 1.0238 (16) | 0.128 (9) | 0.50 |
H12 | 0.7988 | 0.9192 | 1.0546 | 0.153* | 0.50 |
C13 | 1.003 (4) | 0.8186 (14) | 0.9621 (15) | 0.109 (4) | 0.50 |
H13 | 1.1409 | 0.8600 | 0.9478 | 0.131* | 0.50 |
C14 | 1.007 (3) | 0.7216 (16) | 0.9208 (10) | 0.089 (4) | 0.50 |
H14 | 1.1510 | 0.6978 | 0.8771 | 0.107* | 0.50 |
C15 | 1.0002 (5) | 0.1234 (2) | 0.64080 (18) | 0.0965 (8) | |
H15A | 1.0431 | 0.1663 | 0.5806 | 0.116* | |
H15B | 0.8372 | 0.0966 | 0.6407 | 0.116* | |
O1 | 0.2389 (2) | 0.39389 (12) | 0.52819 (9) | 0.0771 (4) | |
O2 | 0.1076 (2) | 0.56551 (11) | 0.58910 (9) | 0.0786 (5) | |
H2 | 0.0056 | 0.5746 | 0.5506 | 0.118* | |
O3 | 0.6562 (3) | 0.56890 (12) | 0.82994 (9) | 0.0821 (5) | |
O4 | 0.9731 (3) | 0.19714 (13) | 0.71375 (11) | 0.0918 (5) | |
C16 | 1.2137 (4) | 0.01969 (19) | 0.65555 (17) | 0.0819 (6) | 0.50 |
C17 | 1.311 (3) | −0.0007 (14) | 0.7341 (13) | 0.123 (6) | 0.50 |
H17 | 1.2647 | 0.0503 | 0.7812 | 0.148* | 0.50 |
C18 | 1.498 (2) | −0.1088 (13) | 0.7431 (10) | 0.118 (4) | 0.50 |
H18 | 1.5568 | −0.1319 | 0.8008 | 0.141* | 0.50 |
C19 | 1.592 (4) | −0.1779 (19) | 0.672 (2) | 0.107 (7) | 0.50 |
H19 | 1.7133 | −0.2461 | 0.6796 | 0.128* | 0.50 |
C20 | 1.506 (2) | −0.1445 (10) | 0.5925 (11) | 0.119 (4) | 0.50 |
H20 | 1.5708 | −0.1903 | 0.5427 | 0.143* | 0.50 |
C21 | 1.3231 (14) | −0.0455 (7) | 0.5771 (6) | 0.102 (2) | 0.50 |
H21 | 1.2735 | −0.0222 | 0.5180 | 0.123* | 0.50 |
C21A | 1.388 (3) | 0.0108 (12) | 0.7188 (12) | 0.087 (4) | 0.50 |
H21A | 1.3649 | 0.0714 | 0.7574 | 0.105* | 0.50 |
C17A | 1.2212 (16) | −0.0818 (6) | 0.6129 (5) | 0.091 (2) | 0.50 |
H17A | 1.0879 | −0.0863 | 0.5792 | 0.110* | 0.50 |
C18A | 1.420 (2) | −0.1752 (10) | 0.6191 (9) | 0.104 (3) | 0.50 |
H18A | 1.4344 | −0.2395 | 0.5851 | 0.124* | 0.50 |
C19A | 1.604 (4) | −0.170 (2) | 0.680 (2) | 0.116 (9) | 0.50 |
H19A | 1.7397 | −0.2329 | 0.6857 | 0.139* | 0.50 |
C20A | 1.588 (3) | −0.0765 (13) | 0.7298 (13) | 0.109 (4) | 0.50 |
H20A | 1.7085 | −0.0737 | 0.7693 | 0.131* | 0.50 |
C11A | 0.945 (5) | 0.8536 (15) | 0.9366 (15) | 0.122 (5) | 0.50 |
H11A | 1.0322 | 0.9136 | 0.9086 | 0.146* | 0.50 |
C9A | 0.8300 (5) | 0.65976 (19) | 0.93627 (17) | 0.0705 (6) | 0.50 |
C10A | 0.986 (4) | 0.7480 (16) | 0.8932 (12) | 0.101 (4) | 0.50 |
H10A | 1.1073 | 0.7352 | 0.8397 | 0.121* | 0.50 |
C12A | 0.777 (5) | 0.870 (2) | 1.021 (2) | 0.118 (8) | 0.50 |
H12A | 0.7512 | 0.9388 | 1.0496 | 0.141* | 0.50 |
C14A | 0.663 (4) | 0.678 (2) | 1.0200 (13) | 0.081 (3) | 0.50 |
H14A | 0.5643 | 0.6216 | 1.0477 | 0.097* | 0.50 |
C13A | 0.645 (4) | 0.776 (2) | 1.0596 (13) | 0.096 (5) | 0.50 |
H13A | 0.5398 | 0.7840 | 1.1172 | 0.115* | 0.50 |
C16A | 1.2137 (4) | 0.01969 (19) | 0.65555 (17) | 0.0819 (6) | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0606 (10) | 0.0610 (12) | 0.0628 (11) | −0.0002 (9) | −0.0110 (9) | −0.0101 (9) |
C2 | 0.0577 (10) | 0.0599 (12) | 0.0602 (11) | −0.0032 (8) | −0.0116 (8) | −0.0069 (9) |
C3 | 0.0648 (11) | 0.0612 (12) | 0.0641 (11) | 0.0030 (8) | −0.0142 (9) | −0.0097 (9) |
C4 | 0.0703 (11) | 0.0595 (12) | 0.0620 (11) | −0.0017 (9) | −0.0167 (9) | −0.0125 (9) |
C5 | 0.0692 (11) | 0.0666 (13) | 0.0666 (12) | 0.0001 (9) | −0.0224 (9) | −0.0100 (10) |
C6 | 0.0713 (11) | 0.0596 (12) | 0.0744 (12) | 0.0063 (9) | −0.0215 (10) | −0.0127 (10) |
C7 | 0.0713 (11) | 0.0648 (13) | 0.0712 (12) | 0.0012 (10) | −0.0203 (9) | −0.0145 (9) |
C8 | 0.0778 (12) | 0.0754 (14) | 0.0830 (14) | −0.0039 (10) | −0.0320 (11) | −0.0114 (11) |
C9 | 0.0755 (13) | 0.0689 (13) | 0.0719 (14) | −0.0086 (12) | −0.0259 (12) | −0.0111 (11) |
C11 | 0.158 (16) | 0.098 (11) | 0.134 (13) | −0.007 (10) | 0.007 (10) | −0.043 (10) |
C10 | 0.144 (13) | 0.095 (10) | 0.103 (12) | −0.048 (9) | −0.001 (8) | −0.017 (8) |
C12 | 0.20 (2) | 0.100 (12) | 0.089 (10) | −0.025 (10) | −0.011 (10) | −0.054 (8) |
C13 | 0.111 (6) | 0.079 (8) | 0.146 (14) | −0.022 (6) | −0.025 (7) | −0.022 (7) |
C14 | 0.090 (4) | 0.078 (7) | 0.096 (10) | −0.009 (4) | −0.006 (6) | −0.018 (6) |
C15 | 0.1051 (16) | 0.0757 (16) | 0.1102 (18) | 0.0201 (12) | −0.0423 (14) | −0.0365 (13) |
O1 | 0.0803 (9) | 0.0747 (9) | 0.0783 (9) | 0.0080 (7) | −0.0301 (7) | −0.0240 (7) |
O2 | 0.0789 (8) | 0.0692 (9) | 0.0882 (10) | 0.0108 (7) | −0.0338 (7) | −0.0184 (7) |
O3 | 0.0962 (10) | 0.0701 (9) | 0.0839 (9) | 0.0106 (7) | −0.0419 (8) | −0.0244 (7) |
O4 | 0.1028 (10) | 0.0712 (10) | 0.1016 (11) | 0.0268 (8) | −0.0480 (8) | −0.0317 (8) |
C16 | 0.0851 (14) | 0.0636 (14) | 0.0955 (17) | 0.0050 (11) | −0.0223 (13) | −0.0177 (12) |
C17 | 0.118 (12) | 0.134 (9) | 0.086 (5) | 0.055 (7) | −0.017 (7) | 0.000 (5) |
C18 | 0.134 (10) | 0.096 (9) | 0.104 (5) | 0.034 (7) | −0.035 (7) | 0.007 (6) |
C19 | 0.131 (12) | 0.051 (9) | 0.136 (13) | 0.002 (7) | −0.035 (11) | −0.007 (8) |
C20 | 0.116 (7) | 0.079 (7) | 0.158 (11) | 0.010 (5) | −0.011 (6) | −0.051 (6) |
C21 | 0.107 (5) | 0.080 (5) | 0.120 (6) | 0.019 (4) | −0.032 (4) | −0.041 (4) |
C21A | 0.082 (6) | 0.072 (4) | 0.107 (9) | 0.013 (4) | −0.023 (5) | −0.037 (5) |
C17A | 0.112 (5) | 0.066 (4) | 0.096 (5) | −0.002 (3) | −0.026 (4) | −0.011 (3) |
C18A | 0.137 (9) | 0.054 (5) | 0.115 (6) | −0.002 (5) | −0.022 (6) | −0.007 (4) |
C19A | 0.090 (9) | 0.087 (15) | 0.138 (14) | 0.036 (8) | 0.012 (11) | 0.002 (9) |
C20A | 0.087 (6) | 0.082 (7) | 0.158 (9) | −0.002 (5) | −0.038 (6) | −0.007 (6) |
C11A | 0.173 (15) | 0.083 (10) | 0.123 (10) | −0.058 (9) | −0.027 (9) | −0.006 (7) |
C9A | 0.0755 (13) | 0.0689 (13) | 0.0719 (14) | −0.0086 (12) | −0.0259 (12) | −0.0111 (11) |
C10A | 0.143 (9) | 0.094 (9) | 0.076 (7) | −0.058 (6) | −0.004 (5) | −0.011 (6) |
C12A | 0.127 (10) | 0.082 (8) | 0.162 (19) | −0.026 (7) | −0.043 (11) | −0.042 (8) |
C14A | 0.098 (5) | 0.088 (9) | 0.059 (6) | −0.027 (5) | −0.002 (4) | −0.017 (5) |
C13A | 0.109 (7) | 0.112 (15) | 0.069 (4) | −0.025 (8) | 0.001 (5) | −0.027 (6) |
C16A | 0.0851 (14) | 0.0636 (14) | 0.0955 (17) | 0.0050 (11) | −0.0223 (13) | −0.0177 (12) |
C1—O1 | 1.236 (2) | C15—H15B | 0.9700 |
C1—O2 | 1.296 (2) | O2—H2 | 0.8200 |
C1—C2 | 1.484 (2) | C16—C17 | 1.302 (18) |
C2—C3 | 1.374 (2) | C16—C21 | 1.424 (8) |
C2—C7 | 1.393 (2) | C17—C18 | 1.45 (2) |
C3—C4 | 1.391 (2) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—C19 | 1.36 (3) |
C4—O3 | 1.366 (2) | C18—H18 | 0.9300 |
C4—C5 | 1.379 (3) | C19—C20 | 1.30 (4) |
C5—C6 | 1.383 (3) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—C21 | 1.379 (14) |
C6—O4 | 1.367 (2) | C20—H20 | 0.9300 |
C6—C7 | 1.381 (3) | C21—H21 | 0.9300 |
C7—H7 | 0.9300 | C21A—C20A | 1.33 (2) |
C8—O3 | 1.425 (2) | C21A—H21A | 0.9300 |
C8—C9 | 1.490 (3) | C17A—C18A | 1.369 (14) |
C8—H8A | 0.9700 | C17A—H17A | 0.9300 |
C8—H8B | 0.9700 | C18A—C19A | 1.42 (4) |
C9—C14 | 1.26 (2) | C18A—H18A | 0.9300 |
C9—C10 | 1.33 (3) | C19A—C20A | 1.36 (3) |
C11—C12 | 1.32 (5) | C19A—H19A | 0.9300 |
C11—C10 | 1.41 (4) | C20A—H20A | 0.9300 |
C11—H11 | 0.9300 | C11A—C12A | 1.40 (3) |
C10—H10 | 0.9300 | C11A—C10A | 1.41 (3) |
C12—C13 | 1.32 (3) | C11A—H11A | 0.9300 |
C12—H12 | 0.9300 | C10A—H10A | 0.9300 |
C13—C14 | 1.34 (3) | C12A—C13A | 1.42 (4) |
C13—H13 | 0.9300 | C12A—H12A | 0.9300 |
C14—H14 | 0.9300 | C14A—C13A | 1.32 (3) |
C15—O4 | 1.413 (3) | C14A—H14A | 0.9300 |
C15—C16 | 1.510 (3) | C13A—H13A | 0.9300 |
C15—H15A | 0.9700 | ||
O1—C1—O2 | 123.33 (16) | C16—C15—H15A | 109.8 |
O1—C1—C2 | 121.00 (16) | O4—C15—H15B | 109.8 |
O2—C1—C2 | 115.67 (16) | C16—C15—H15B | 109.8 |
C3—C2—C7 | 121.05 (17) | H15A—C15—H15B | 108.3 |
C3—C2—C1 | 120.35 (16) | C1—O2—H2 | 109.5 |
C7—C2—C1 | 118.59 (16) | C4—O3—C8 | 118.81 (14) |
C2—C3—C4 | 119.62 (17) | C6—O4—C15 | 117.70 (15) |
C2—C3—H3 | 120.2 | C17—C16—C21 | 121.6 (8) |
C4—C3—H3 | 120.2 | C17—C16—C15 | 120.5 (8) |
O3—C4—C5 | 124.69 (16) | C21—C16—C15 | 117.4 (4) |
O3—C4—C3 | 115.23 (16) | C16—C17—C18 | 115.3 (14) |
C5—C4—C3 | 120.07 (17) | C16—C17—H17 | 122.4 |
C4—C5—C6 | 119.60 (17) | C18—C17—H17 | 122.4 |
C4—C5—H5 | 120.2 | C19—C18—C17 | 123.6 (17) |
C6—C5—H5 | 120.2 | C19—C18—H18 | 118.2 |
O4—C6—C7 | 124.09 (17) | C17—C18—H18 | 118.2 |
O4—C6—C5 | 114.69 (16) | C20—C19—C18 | 117.0 (17) |
C7—C6—C5 | 121.21 (17) | C20—C19—H19 | 121.5 |
C6—C7—C2 | 118.43 (17) | C18—C19—H19 | 121.5 |
C6—C7—H7 | 120.8 | C19—C20—C21 | 124.2 (14) |
C2—C7—H7 | 120.8 | C19—C20—H20 | 117.9 |
O3—C8—C9 | 107.77 (15) | C21—C20—H20 | 117.9 |
O3—C8—H8A | 110.2 | C20—C21—C16 | 117.1 (9) |
C9—C8—H8A | 110.2 | C20—C21—H21 | 121.4 |
O3—C8—H8B | 110.2 | C16—C21—H21 | 121.4 |
C9—C8—H8B | 110.2 | C20A—C21A—H21A | 116.9 |
H8A—C8—H8B | 108.5 | C18A—C17A—H17A | 119.2 |
C14—C9—C10 | 114.7 (15) | C17A—C18A—C19A | 117.3 (13) |
C14—C9—C8 | 122.2 (8) | C17A—C18A—H18A | 121.3 |
C10—C9—C8 | 123.1 (13) | C19A—C18A—H18A | 121.3 |
C12—C11—C10 | 112 (3) | C20A—C19A—C18A | 122.3 (15) |
C12—C11—H11 | 124.2 | C20A—C19A—H19A | 118.8 |
C10—C11—H11 | 124.2 | C18A—C19A—H19A | 118.8 |
C9—C10—C11 | 126 (3) | C21A—C20A—C19A | 116.2 (16) |
C9—C10—H10 | 116.9 | C21A—C20A—H20A | 121.9 |
C11—C10—H10 | 116.9 | C19A—C20A—H20A | 121.9 |
C13—C12—C11 | 124 (3) | C12A—C11A—C10A | 121.5 (19) |
C13—C12—H12 | 117.9 | C12A—C11A—H11A | 119.3 |
C11—C12—H12 | 117.9 | C10A—C11A—H11A | 119.3 |
C12—C13—C14 | 118 (2) | C11A—C10A—H10A | 121.4 |
C12—C13—H13 | 121.1 | C11A—C12A—C13A | 117 (2) |
C14—C13—H13 | 121.1 | C11A—C12A—H12A | 121.6 |
C9—C14—C13 | 125.4 (14) | C13A—C12A—H12A | 121.6 |
C9—C14—H14 | 117.3 | C13A—C14A—H14A | 120.4 |
C13—C14—H14 | 117.3 | C14A—C13A—C12A | 125 (2) |
O4—C15—C16 | 109.24 (18) | C14A—C13A—H13A | 117.6 |
O4—C15—H15A | 109.8 | C12A—C13A—H13A | 117.6 |
O1—C1—C2—C3 | 179.21 (16) | C10—C9—C14—C13 | 1.5 (18) |
O2—C1—C2—C3 | −1.0 (2) | C8—C9—C14—C13 | −177.8 (11) |
O1—C1—C2—C7 | 0.4 (3) | C12—C13—C14—C9 | 0 (3) |
O2—C1—C2—C7 | −179.85 (16) | C5—C4—O3—C8 | 4.4 (3) |
C7—C2—C3—C4 | −1.0 (3) | C3—C4—O3—C8 | −175.13 (16) |
C1—C2—C3—C4 | −179.76 (15) | C9—C8—O3—C4 | 173.58 (17) |
C2—C3—C4—O3 | −179.84 (15) | C7—C6—O4—C15 | 12.0 (3) |
C2—C3—C4—C5 | 0.6 (3) | C5—C6—O4—C15 | −167.82 (19) |
O3—C4—C5—C6 | −179.43 (16) | C16—C15—O4—C6 | 176.14 (18) |
C3—C4—C5—C6 | 0.1 (3) | O4—C15—C16—C17 | 11.0 (9) |
C4—C5—C6—O4 | 179.37 (17) | O4—C15—C16—C21 | −161.8 (4) |
C4—C5—C6—C7 | −0.4 (3) | C21—C16—C17—C18 | −12.9 (17) |
O4—C6—C7—C2 | −179.70 (18) | C15—C16—C17—C18 | 174.6 (9) |
C5—C6—C7—C2 | 0.1 (3) | C16—C17—C18—C19 | 8 (2) |
C3—C2—C7—C6 | 0.6 (3) | C17—C18—C19—C20 | −1 (3) |
C1—C2—C7—C6 | 179.44 (16) | C18—C19—C20—C21 | −1 (3) |
O3—C8—C9—C14 | −114.4 (7) | C19—C20—C21—C16 | −3.7 (18) |
O3—C8—C9—C10 | 66.4 (9) | C17—C16—C21—C20 | 11.5 (13) |
C14—C9—C10—C11 | 1 (2) | C15—C16—C21—C20 | −175.8 (6) |
C8—C9—C10—C11 | 179.8 (15) | C17A—C18A—C19A—C20A | −1 (3) |
C12—C11—C10—C9 | −3 (3) | C18A—C19A—C20A—C21A | 0 (3) |
C10—C11—C12—C13 | 4 (4) | C10A—C11A—C12A—C13A | −1 (3) |
C11—C12—C13—C14 | −3 (4) | C11A—C12A—C13A—C14A | −3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 1.82 | 2.6333 (18) | 175 |
C20—H20···O1ii | 0.93 | 2.66 | 3.507 (13) | 153 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+2, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C21H18O4 |
Mr | 334.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 5.2801 (2), 11.6830 (5), 14.4803 (7) |
α, β, γ (°) | 83.303 (2), 80.775 (2), 79.031 (1) |
V (Å3) | 862.17 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.43 × 0.11 × 0.10 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5626, 3084, 1801 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.163, 1.03 |
No. of reflections | 3084 |
No. of parameters | 316 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.15 |
Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 1.82 | 2.6333 (18) | 174.5 |
C20—H20···O1ii | 0.93 | 2.66 | 3.507 (13) | 152.6 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+2, −y, −z+1. |
Acknowledgements
RMF is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge licence to the Cambridge Structural Database. RMF also thanks the Universidad del Valle, Colombia, and CG thanks the Universidad San Buenaventura, Cali, Colombia, for partial financial support.
References
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Dendrimer chemistry provides new opportunities of research in design of supramolecular architectures (Fréchet, 2002). 3,5-Bis-benzyloxy-benzoic acid (I) was used for the synthesis of luminescent lanthanide coordination complexes that display unique line-like emission bands (Sivakumar et al., 2010; Remya et al., 2008). Lanthanide benzoates and their derivatives have potential applications in a wide variety of fields because their novel luminescent and magnetic properties (Busskamp et al., 2007). The title compound was also used in the synthesis of monodispersed dendritic polyesters with removable chain ends using a convergent growth process (Hawker & Fréchet, 1992). Other related compounds were crystallized and studied by X-ray diffraction (Gainsford et al., 2009; Zhu et al., 2009) and their parameters can be used to compare with the parameters of the title system. A perspective view of the molecule of (I), showing the atomic numbering scheme, is given in Fig. 1. The title compound crystallizes in the triclinic system with a P-1 space group. The outer benzyl rings are disordered over two resolved positions in a 0.50 ratio. The molecules are bonded by intermolecular O—H···O hydrogen bonds of moderate character (Desiraju & Steiner, 1999). Indeed, carbonylic O2 and O1 are linked with an O···O distance of 2.633 (2) Å. The propagation of these interactions generate centrosymmetric rings with graphs-set notation R22(8) (Etter, 1990). Other weak C—H···O intermolecular interactions (Nardelli, 1995) contribute to stabilization of the molecules along b (Fig. 2). Other classical hydrogen bond interactions are not exhibited in the crystal packing. In the title structure, the O—CH2 groups adopt a syn-anti conformation with respect to the central phenyl ring, similar to the behavior presented in the 1,3-Dibenzyloxy-5-(bromomethyl)-benzene system (Zhu et al., 2009), while in other similar structures, the O—CH2 groups adopt a syn-syn conformation (Xiao et al., 2007). The O—CH2 groups, C4—O3—C8—C9 and C6—O4—C15—C16 are essentially planar (r.m.s. deviation of non-hydrogen atoms= 0.0355 Å and 0.0217 Å respectivelly) and form dihedral angles of 4.1 (2)° and 10.9 (4)° with the central phenyl ring.