organic compounds
4-Benzyloxy-1,1′-biphenyl
aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 Pulau Pinang, Malaysia, bDepartment of P.G. Studies in Analytical Chemistry, Alva's College, Moodbidri, Karnataka 574 227, India, and cDepartment of P.G. Studies in Chemistry, Alva's College, Moodbidri, Karnataka 574 227, India
*Correspondence e-mail: farook@usm.my
In the title compound, C19H16O, the dihedral angle between the benzene rings of the biphenyl unit is 1.54 (13)° and the C—O—C—C torsion angle is 174.4 (2)°. In the crystal, very weak C—H⋯π interactions link the molecules into a three-dimensional network.
Keywords: crystal structure; aryl ether; synthesis.
CCDC reference: 1460794
Structure description
Many diaryl ; Frlan & Kikelj, 2006). The crystal structures of some aryl viz., 2,4-dichloro-1-[1-(2,4 dichlorobenzyloxy)ethyl]benzene (Jasinski et al., 2010) and 2,6-bis[2-(4-benzyloxyphenyl)ethyl]biphenyl (Moratti et al., 2007) have been reported. As part of our studies in this area, the synthesis and structure of the title compound are reported.
exhibit various pharmacological properties including anti-bacterial, anti-inflammatory, antifungal and herbicidal activities (Ley & Thomas, 2003The title molecule (Fig. 1) consists of three benzene rings, C1–C6 (A), C7–C12 (B) and C14–C19 (C). The dihedral angles A/B, A/C and B/C are 1.54 (13), 61.50 (14) and 62.80 (14)°, respectively. Five weak C—H⋯π interactions are observed in the (Table 1). The crystal packing is illustrated in Fig. 2.
Synthesis and crystallization
A mixture of (1,1′-biphenyl)-4-ol (1.70 g, 0.01 mol) and benzyl chloride (5 ml) was refluxed for 30 min. The reaction mixture was cooled and poured into 25 ml hexane. The precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from 1,4-dioxane solution by the slow evaporation method; m.p. 421–425 K, yield 85%.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1460794
10.1107/S2414314616003989/hb4023sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616003989/hb4023Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616003989/hb4023Isup3.cml
Amixtureof[1,1'-biphenyl]-4-ol(1.70 g,0.01 mol) andbenzylchloride(5 ml) was refluxed for30minutes·Thereactionmixturewascooledandpouredinto25mlhexane·Theprecipitatewascollectedbyfiltrationandpurifiedbyrecrystallizationfromethanol·Singlecrystalsweregrownfrom1,4-dioxanebyslowevaporationmethod;m.p.421–425 K·Yield:85%.
A mixture of (1,1'-biphenyl)-4-ol (1.70 g, 0.01 mol) and benzyl chloride (5 ml) was refluxed for 30 min. The reaction mixture was cooled and poured into 25 ml hexane. The precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from 1,4-dioxane by the slow evaporation method; m.p. 421–425 K, yield 85%.
Many diaryl
exhibit various pharmacological properties including anti-bacterial, anti-inflammatory, antifungal and herbicidal activities (Ley & Thomas, 2003; Frlan & Kikelj, 2006). The crystal structures of some aryl viz., 2,4-dichloro-1-[1-(2,4 dichlorobenzyloxy)ethyl]benzene (Jasinski et al., 2010) and 2,6-bis[2-(4-benzyloxyphenyl)ethyl]biphenyl (Moratti et al., 2007) have been reported. As part of our studies in this area, the synthesis and structure of the title compound are reported.The title molecule consists of three benzene rings, C1–C6 (A), C7–C12 (B) and C14–C19 (C). The dihedral angles A/B, A/C and B/C are 1.54 (13), 61.50 (14) and 62.80 (14)°, respectively. Five weak C—H···π interactions are observed in the (Table 2).
Data collection: APEX2 (Bruker, 2010); cell
SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. | |
Fig. 2. The crystal packing, viewed along the b axis. |
C19H16O | F(000) = 552 |
Mr = 260.32 | Dx = 1.253 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 31.270 (2) Å | Cell parameters from 7054 reflections |
b = 5.6720 (4) Å | θ = 2.6–31.7° |
c = 7.8812 (5) Å | µ = 0.08 mm−1 |
β = 99.271 (3)° | T = 296 K |
V = 1379.58 (16) Å3 | Plate, colourless |
Z = 4 | 0.39 × 0.31 × 0.09 mm |
Bruker APEXII CCD diffractometer | 2218 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.027 |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | θmax = 25.0°, θmin = 2.6° |
Tmin = 0.891, Tmax = 0.969 | h = −36→36 |
18200 measured reflections | k = −6→6 |
2435 independent reflections | l = −9→9 |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0802P)2 + 0.3664P] where P = (Fo2 + 2Fc2)/3 |
S = 0.87 | (Δ/σ)max < 0.001 |
2435 reflections | Δρmax = 0.12 e Å−3 |
181 parameters | Δρmin = −0.12 e Å−3 |
C19H16O | V = 1379.58 (16) Å3 |
Mr = 260.32 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 31.270 (2) Å | µ = 0.08 mm−1 |
b = 5.6720 (4) Å | T = 296 K |
c = 7.8812 (5) Å | 0.39 × 0.31 × 0.09 mm |
β = 99.271 (3)° |
Bruker APEXII CCD diffractometer | 2435 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | 2218 reflections with I > 2σ(I) |
Tmin = 0.891, Tmax = 0.969 | Rint = 0.027 |
18200 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 2 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 0.87 | Δρmax = 0.12 e Å−3 |
2435 reflections | Δρmin = −0.12 e Å−3 |
181 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 | ||
O1 | 0.44220 (6) | 0.2333 (3) | 1.0798 (2) | 0.0538 (5) | |
C1 | 0.23730 (9) | 0.4280 (5) | 0.7983 (4) | 0.0517 (7) | |
H1A | 0.2475 | 0.5521 | 0.8709 | 0.062* | |
C2 | 0.19447 (9) | 0.4248 (5) | 0.7236 (4) | 0.0579 (8) | |
H2A | 0.1761 | 0.5458 | 0.7463 | 0.069* | |
C3 | 0.17851 (9) | 0.2446 (5) | 0.6158 (4) | 0.0538 (7) | |
H3A | 0.1495 | 0.2416 | 0.5659 | 0.065* | |
C4 | 0.20609 (9) | 0.0691 (5) | 0.5831 (4) | 0.0588 (8) | |
H4A | 0.1958 | −0.0529 | 0.5088 | 0.071* | |
C5 | 0.24892 (9) | 0.0712 (5) | 0.6590 (4) | 0.0515 (7) | |
H5A | 0.2670 | −0.0512 | 0.6362 | 0.062* | |
C6 | 0.26585 (8) | 0.2510 (4) | 0.7683 (3) | 0.0377 (6) | |
C7 | 0.31216 (8) | 0.2517 (4) | 0.8516 (3) | 0.0366 (6) | |
C8 | 0.34084 (9) | 0.0771 (5) | 0.8203 (4) | 0.0523 (8) | |
H8A | 0.3309 | −0.0435 | 0.7442 | 0.063* | |
C9 | 0.38322 (9) | 0.0756 (5) | 0.8973 (4) | 0.0553 (8) | |
H9A | 0.4013 | −0.0461 | 0.8738 | 0.066* | |
C10 | 0.39943 (8) | 0.2524 (4) | 1.0094 (3) | 0.0408 (6) | |
C11 | 0.37210 (8) | 0.4295 (5) | 1.0437 (3) | 0.0491 (7) | |
H11A | 0.3823 | 0.5502 | 1.1194 | 0.059* | |
C12 | 0.32920 (8) | 0.4267 (5) | 0.9646 (3) | 0.0476 (7) | |
H12A | 0.3111 | 0.5479 | 0.9886 | 0.057* | |
C13 | 0.45998 (9) | 0.4022 (5) | 1.2055 (4) | 0.0512 (7) | |
H13A | 0.4429 | 0.4080 | 1.2977 | 0.061* | |
H13B | 0.4598 | 0.5575 | 1.1539 | 0.061* | |
C14 | 0.50538 (8) | 0.3302 (5) | 1.2746 (3) | 0.0434 (6) | |
C15 | 0.51377 (9) | 0.1223 (5) | 1.3677 (4) | 0.0527 (7) | |
H15A | 0.4909 | 0.0250 | 1.3852 | 0.063* | |
C16 | 0.55562 (10) | 0.0597 (5) | 1.4339 (4) | 0.0595 (8) | |
H16A | 0.5611 | −0.0792 | 1.4963 | 0.071* | |
C17 | 0.58958 (10) | 0.2035 (6) | 1.4075 (4) | 0.0612 (8) | |
H17A | 0.6179 | 0.1610 | 1.4516 | 0.073* | |
C18 | 0.58158 (9) | 0.4071 (6) | 1.3169 (4) | 0.0587 (7) | |
H18A | 0.6045 | 0.5045 | 1.3004 | 0.070* | |
C19 | 0.53974 (9) | 0.4697 (5) | 1.2493 (4) | 0.0503 (7) | |
H19A | 0.5347 | 0.6079 | 1.1858 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0395 (10) | 0.0632 (12) | 0.0561 (11) | 0.0062 (8) | −0.0001 (8) | −0.0172 (9) |
C1 | 0.0494 (17) | 0.0478 (16) | 0.0544 (17) | 0.0041 (11) | −0.0016 (13) | −0.0105 (12) |
C2 | 0.0472 (16) | 0.0626 (18) | 0.0615 (19) | 0.0129 (13) | 0.0016 (14) | −0.0039 (14) |
C3 | 0.0393 (14) | 0.0658 (19) | 0.0537 (16) | −0.0012 (12) | −0.0006 (12) | 0.0044 (13) |
C4 | 0.0514 (18) | 0.0628 (18) | 0.0591 (19) | −0.0092 (14) | −0.0009 (14) | −0.0135 (14) |
C5 | 0.0452 (16) | 0.0525 (16) | 0.0556 (17) | 0.0035 (12) | 0.0049 (13) | −0.0130 (12) |
C6 | 0.0388 (14) | 0.0411 (13) | 0.0338 (13) | −0.0009 (9) | 0.0077 (10) | 0.0044 (9) |
C7 | 0.0416 (14) | 0.0372 (13) | 0.0317 (12) | −0.0009 (9) | 0.0081 (10) | 0.0024 (9) |
C8 | 0.0480 (17) | 0.0464 (15) | 0.0590 (18) | 0.0032 (11) | −0.0024 (14) | −0.0199 (12) |
C9 | 0.0491 (17) | 0.0514 (16) | 0.0630 (19) | 0.0128 (12) | 0.0019 (14) | −0.0180 (13) |
C10 | 0.0373 (14) | 0.0476 (14) | 0.0369 (14) | 0.0018 (10) | 0.0043 (11) | −0.0021 (10) |
C11 | 0.0476 (18) | 0.0465 (16) | 0.0510 (17) | 0.0005 (11) | 0.0015 (13) | −0.0140 (12) |
C12 | 0.0429 (16) | 0.0441 (14) | 0.0547 (17) | 0.0073 (11) | 0.0041 (13) | −0.0124 (12) |
C13 | 0.0446 (15) | 0.0550 (16) | 0.0513 (16) | −0.0010 (12) | 0.0000 (12) | −0.0087 (12) |
C14 | 0.0415 (14) | 0.0481 (13) | 0.0384 (13) | 0.0008 (11) | −0.0002 (11) | −0.0059 (11) |
C15 | 0.0520 (16) | 0.0490 (14) | 0.0557 (17) | −0.0058 (12) | 0.0045 (13) | 0.0000 (13) |
C16 | 0.067 (2) | 0.0510 (16) | 0.0568 (17) | 0.0114 (14) | −0.0022 (15) | 0.0046 (13) |
C17 | 0.0471 (16) | 0.071 (2) | 0.0611 (18) | 0.0112 (14) | −0.0058 (13) | −0.0100 (16) |
C18 | 0.0443 (16) | 0.0687 (19) | 0.0619 (17) | −0.0106 (14) | 0.0052 (13) | −0.0074 (15) |
C19 | 0.0522 (17) | 0.0509 (14) | 0.0464 (14) | −0.0053 (12) | 0.0041 (12) | 0.0033 (12) |
O1—C10 | 1.367 (3) | C9—H9A | 0.9300 |
O1—C13 | 1.425 (3) | C10—C11 | 1.374 (4) |
C1—C2 | 1.374 (4) | C11—C12 | 1.386 (4) |
C1—C6 | 1.389 (4) | C11—H11A | 0.9300 |
C1—H1A | 0.9300 | C12—H12A | 0.9300 |
C2—C3 | 1.370 (4) | C13—C14 | 1.493 (4) |
C2—H2A | 0.9300 | C13—H13A | 0.9700 |
C3—C4 | 1.369 (4) | C13—H13B | 0.9700 |
C3—H3A | 0.9300 | C14—C19 | 1.374 (4) |
C4—C5 | 1.376 (4) | C14—C15 | 1.391 (4) |
C4—H4A | 0.9300 | C15—C16 | 1.375 (4) |
C5—C6 | 1.384 (4) | C15—H15A | 0.9300 |
C5—H5A | 0.9300 | C16—C17 | 1.381 (5) |
C6—C7 | 1.491 (3) | C16—H16A | 0.9300 |
C7—C12 | 1.382 (4) | C17—C18 | 1.359 (4) |
C7—C8 | 1.384 (4) | C17—H17A | 0.9300 |
C8—C9 | 1.366 (4) | C18—C19 | 1.378 (4) |
C8—H8A | 0.9300 | C18—H18A | 0.9300 |
C9—C10 | 1.378 (4) | C19—H19A | 0.9300 |
C10—O1—C13 | 118.39 (19) | C10—C11—C12 | 119.4 (2) |
C2—C1—C6 | 121.7 (3) | C10—C11—H11A | 120.3 |
C2—C1—H1A | 119.1 | C12—C11—H11A | 120.3 |
C6—C1—H1A | 119.1 | C7—C12—C11 | 122.9 (2) |
C3—C2—C1 | 120.6 (3) | C7—C12—H12A | 118.6 |
C3—C2—H2A | 119.7 | C11—C12—H12A | 118.6 |
C1—C2—H2A | 119.7 | O1—C13—C14 | 108.1 (2) |
C4—C3—C2 | 118.8 (3) | O1—C13—H13A | 110.1 |
C4—C3—H3A | 120.6 | C14—C13—H13A | 110.1 |
C2—C3—H3A | 120.6 | O1—C13—H13B | 110.1 |
C3—C4—C5 | 120.7 (3) | C14—C13—H13B | 110.1 |
C3—C4—H4A | 119.7 | H13A—C13—H13B | 108.4 |
C5—C4—H4A | 119.7 | C19—C14—C15 | 118.6 (2) |
C4—C5—C6 | 121.7 (2) | C19—C14—C13 | 120.6 (2) |
C4—C5—H5A | 119.2 | C15—C14—C13 | 120.8 (2) |
C6—C5—H5A | 119.2 | C16—C15—C14 | 120.4 (3) |
C5—C6—C1 | 116.5 (2) | C16—C15—H15A | 119.8 |
C5—C6—C7 | 121.5 (2) | C14—C15—H15A | 119.8 |
C1—C6—C7 | 121.9 (2) | C15—C16—C17 | 119.9 (3) |
C12—C7—C8 | 115.8 (2) | C15—C16—H16A | 120.1 |
C12—C7—C6 | 122.1 (2) | C17—C16—H16A | 120.1 |
C8—C7—C6 | 122.1 (2) | C18—C17—C16 | 120.0 (3) |
C9—C8—C7 | 122.4 (2) | C18—C17—H17A | 120.0 |
C9—C8—H8A | 118.8 | C16—C17—H17A | 120.0 |
C7—C8—H8A | 118.8 | C17—C18—C19 | 120.3 (3) |
C8—C9—C10 | 120.7 (2) | C17—C18—H18A | 119.8 |
C8—C9—H9A | 119.7 | C19—C18—H18A | 119.8 |
C10—C9—H9A | 119.7 | C14—C19—C18 | 120.8 (3) |
O1—C10—C11 | 125.2 (2) | C14—C19—H19A | 119.6 |
O1—C10—C9 | 115.9 (2) | C18—C19—H19A | 119.6 |
C11—C10—C9 | 118.8 (2) | ||
C6—C1—C2—C3 | −0.1 (5) | C8—C9—C10—C11 | 0.6 (4) |
C1—C2—C3—C4 | −0.5 (5) | O1—C10—C11—C12 | −179.4 (2) |
C2—C3—C4—C5 | 1.0 (5) | C9—C10—C11—C12 | −0.3 (4) |
C3—C4—C5—C6 | −1.0 (5) | C8—C7—C12—C11 | −0.4 (4) |
C4—C5—C6—C1 | 0.4 (4) | C6—C7—C12—C11 | 179.7 (2) |
C4—C5—C6—C7 | 179.4 (2) | C10—C11—C12—C7 | 0.2 (4) |
C2—C1—C6—C5 | 0.1 (4) | C10—O1—C13—C14 | 174.4 (2) |
C2—C1—C6—C7 | −178.9 (2) | O1—C13—C14—C19 | 115.6 (3) |
C5—C6—C7—C12 | −178.2 (3) | O1—C13—C14—C15 | −65.1 (3) |
C1—C6—C7—C12 | 0.7 (3) | C19—C14—C15—C16 | 0.6 (4) |
C5—C6—C7—C8 | 1.9 (3) | C13—C14—C15—C16 | −178.7 (2) |
C1—C6—C7—C8 | −179.2 (3) | C14—C15—C16—C17 | −0.2 (4) |
C12—C7—C8—C9 | 0.7 (4) | C15—C16—C17—C18 | 0.3 (4) |
C6—C7—C8—C9 | −179.4 (3) | C16—C17—C18—C19 | −0.8 (5) |
C7—C8—C9—C10 | −0.8 (5) | C15—C14—C19—C18 | −1.0 (4) |
C13—O1—C10—C11 | 3.3 (4) | C13—C14—C19—C18 | 178.2 (3) |
C13—O1—C10—C9 | −175.8 (3) | C17—C18—C19—C14 | 1.1 (4) |
C8—C9—C10—O1 | 179.7 (3) |
Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C7–C12 and C14–C19 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···Cg1i | 0.93 | 2.99 | 3.700 (3) | 134 |
C4—H4A···Cg1ii | 0.93 | 2.97 | 3.700 (3) | 134 |
C8—H8A···Cg2ii | 0.93 | 2.96 | 3.687 (3) | 137 |
C11—H11A···Cg2i | 0.93 | 2.93 | 3.650 (3) | 135 |
C19—H19A···Cg3iii | 0.93 | 2.90 | 3.591 (3) | 133 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y, z−1/2; (iii) x, −y+1, z−1/2. |
Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C7–C12 and C14–C19 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···Cg1i | 0.93 | 2.99 | 3.700 (3) | 134 |
C4—H4A···Cg1ii | 0.93 | 2.97 | 3.700 (3) | 134 |
C8—H8A···Cg2ii | 0.93 | 2.96 | 3.687 (3) | 137 |
C11—H11A···Cg2i | 0.93 | 2.93 | 3.650 (3) | 135 |
C19—H19A···Cg3iii | 0.93 | 2.90 | 3.591 (3) | 133 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y, z−1/2; (iii) x, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H16O |
Mr | 260.32 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 296 |
a, b, c (Å) | 31.270 (2), 5.6720 (4), 7.8812 (5) |
β (°) | 99.271 (3) |
V (Å3) | 1379.58 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.39 × 0.31 × 0.09 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2010) |
Tmin, Tmax | 0.891, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18200, 2435, 2218 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.104, 0.87 |
No. of reflections | 2435 |
No. of parameters | 181 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.12 |
Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick 2008), SHELXL2014 (Sheldrick, 2015), SHELXTL (Sheldrick 2008).
Acknowledgements
SS and SDK thank Alva's Education Foundation, Moodbidri, for providing research facilities. FA is grateful for USM research grants 1001/PKIMIA/846017 and 1001/PKIMIA/811269, which partially supported this research.
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