organic compounds
Ethyl 4,4′′-difluoro-5′-methoxy-1,1′:3′,1′′-terphenyl-4′-carboxylate
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
*Correspondence e-mail: hkfun@usm.my
In the title compound, C22H18F2O3, the two fluoro-substituted rings form dihedral angles of 25.89 (15) and 55.00 (12)° with the central benzene ring. The ethoxy group in the molecule is disordered over two positions with a site-occupancy ratio of 0.662 (7):0.338 (7). In the crystal, molecules are linked by C—H⋯O hydrogen bonds into chains along the a axis. The crystal packing is further stabilized by C—H⋯π and π—π interactions, with centroid–centroid distances of 3.8605 (15) Å.
Related literature
For a related structure and background to terphenyls, see: Fun et al. (2011); Samshuddin et al. (2011). For the synthesis, see: Kotnis (1990). For reference bond lengths, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S160053681105344X/rz2682sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681105344X/rz2682Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681105344X/rz2682Isup3.cml
The title compound was prepared by the aromatization of a cyclohexenone derivative, ethyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate, using iodine and methanol at reflux condition (Kotnis, 1990). Single crystals of the product were grown from methanol by slow evaporation method (m.p. 383 K).
All H atoms were positioned geometrically [C—H = 0.93, 0.96 or 0.97 Å] and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating group model was applied to the methyl group. The ethoxy unit was disordered over two positions with a site-occupancy ratio of 0.662 (7):0.338 (7). The same Uij parameters were used for atoms pairs C21/C21X and C22/C22X. The C13–C18 benzene ring was refined using a rigid regular hexagon model with a bond length of 1.39 Å. 2085 Friedel pairs were merged in the last
cycles.Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C22H18F2O3 | F(000) = 768 |
Mr = 368.36 | Dx = 1.319 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3149 reflections |
a = 8.5197 (11) Å | θ = 2.3–22.9° |
b = 9.5225 (12) Å | µ = 0.10 mm−1 |
c = 22.871 (3) Å | T = 296 K |
V = 1855.5 (4) Å3 | Block, colourless |
Z = 4 | 0.43 × 0.21 × 0.15 mm |
Bruker APEX DUO CCD area-detector diffractometer | 3036 independent reflections |
Radiation source: fine-focus sealed tube | 2131 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ϕ and ω scans | θmax = 30.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −11→11 |
Tmin = 0.958, Tmax = 0.986 | k = −13→9 |
11701 measured reflections | l = −26→32 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0841P)2 + 0.2095P] where P = (Fo2 + 2Fc2)/3 |
3036 reflections | (Δ/σ)max = 0.011 |
251 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C22H18F2O3 | V = 1855.5 (4) Å3 |
Mr = 368.36 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.5197 (11) Å | µ = 0.10 mm−1 |
b = 9.5225 (12) Å | T = 296 K |
c = 22.871 (3) Å | 0.43 × 0.21 × 0.15 mm |
Bruker APEX DUO CCD area-detector diffractometer | 3036 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2131 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.986 | Rint = 0.026 |
11701 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.20 e Å−3 |
3036 reflections | Δρmin = −0.23 e Å−3 |
251 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) | |
F1 | −0.2161 (4) | 0.4152 (4) | −0.32486 (9) | 0.1192 (10) | |
F2 | −0.0906 (3) | −0.0580 (3) | 0.15941 (11) | 0.1145 (10) | |
O1 | 0.2205 (3) | 0.7197 (2) | −0.00201 (11) | 0.0713 (6) | |
O2 | 0.3043 (3) | 0.4532 (3) | 0.09557 (11) | 0.0776 (7) | |
C1 | −0.1600 (4) | 0.4267 (5) | −0.26928 (13) | 0.0778 (11) | |
C2 | −0.0345 (5) | 0.5148 (5) | −0.25967 (14) | 0.0806 (11) | |
H2A | 0.0111 | 0.5650 | −0.2901 | 0.097* | |
C3 | 0.0212 (4) | 0.5260 (4) | −0.20305 (13) | 0.0687 (9) | |
H3A | 0.1063 | 0.5843 | −0.1954 | 0.082* | |
C4 | −0.0473 (3) | 0.4518 (3) | −0.15723 (11) | 0.0503 (6) | |
C5 | −0.1719 (3) | 0.3640 (3) | −0.16957 (13) | 0.0569 (7) | |
H5A | −0.2183 | 0.3127 | −0.1396 | 0.068* | |
C6 | −0.2285 (4) | 0.3514 (4) | −0.22611 (14) | 0.0708 (9) | |
H6A | −0.3124 | 0.2920 | −0.2343 | 0.085* | |
C7 | 0.0110 (3) | 0.4665 (3) | −0.09605 (11) | 0.0477 (6) | |
C8 | 0.0859 (3) | 0.5911 (3) | −0.07870 (12) | 0.0524 (6) | |
H8A | 0.0974 | 0.6644 | −0.1052 | 0.063* | |
C9 | 0.1428 (3) | 0.6052 (3) | −0.02228 (13) | 0.0528 (6) | |
C10 | 0.1231 (3) | 0.4972 (3) | 0.01847 (12) | 0.0502 (6) | |
C11 | 0.0447 (3) | 0.3755 (3) | 0.00194 (12) | 0.0485 (6) | |
C12 | −0.0081 (3) | 0.3612 (3) | −0.05553 (12) | 0.0493 (6) | |
H12A | −0.0574 | 0.2783 | −0.0667 | 0.059* | |
C13 | 0.0119 (3) | 0.26039 (16) | 0.04462 (8) | 0.0530 (6) | |
C14 | −0.0684 (3) | 0.28881 (19) | 0.09618 (9) | 0.0701 (9) | |
H14A | −0.0987 | 0.3803 | 0.1049 | 0.084* | |
C15 | −0.1035 (3) | 0.1805 (3) | 0.13478 (8) | 0.0852 (11) | |
H15A | −0.1572 | 0.1995 | 0.1693 | 0.102* | |
C16 | −0.0582 (3) | 0.0438 (2) | 0.12181 (10) | 0.0783 (10) | |
C17 | 0.0221 (3) | 0.01533 (15) | 0.07024 (10) | 0.0765 (10) | |
H17A | 0.0524 | −0.0762 | 0.0616 | 0.092* | |
C18 | 0.0571 (3) | 0.12364 (19) | 0.03165 (8) | 0.0649 (8) | |
H18A | 0.1109 | 0.1046 | −0.0029 | 0.078* | |
C19 | 0.1921 (4) | 0.5144 (3) | 0.07789 (14) | 0.0601 (7) | |
C20 | 0.2508 (5) | 0.8306 (3) | −0.04159 (18) | 0.0758 (10) | |
H20A | 0.3045 | 0.9051 | −0.0216 | 0.114* | |
H20B | 0.1533 | 0.8653 | −0.0570 | 0.114* | |
H20C | 0.3150 | 0.7968 | −0.0731 | 0.114* | |
O3 | 0.0943 (6) | 0.5935 (6) | 0.1127 (2) | 0.0681 (13) | 0.662 (7) |
C21 | 0.1430 (9) | 0.6182 (10) | 0.1721 (3) | 0.101 (2) | 0.662 (7) |
H21A | 0.0502 | 0.6354 | 0.1956 | 0.122* | 0.662 (7) |
H21B | 0.1920 | 0.5333 | 0.1868 | 0.122* | 0.662 (7) |
C22 | 0.2433 (17) | 0.7258 (11) | 0.1799 (5) | 0.162 (5) | 0.662 (7) |
H22A | 0.2898 | 0.7191 | 0.2181 | 0.243* | 0.662 (7) |
H22B | 0.1875 | 0.8130 | 0.1766 | 0.243* | 0.662 (7) |
H22C | 0.3241 | 0.7219 | 0.1507 | 0.243* | 0.662 (7) |
O3X | 0.1537 (10) | 0.6375 (9) | 0.1002 (4) | 0.0542 (19) | 0.338 (7) |
C21X | 0.231 (2) | 0.674 (2) | 0.1527 (5) | 0.101 (2) | 0.338 (7) |
H21C | 0.2259 | 0.7743 | 0.1595 | 0.122* | 0.338 (7) |
H21D | 0.3405 | 0.6455 | 0.1515 | 0.122* | 0.338 (7) |
C22X | 0.1341 (17) | 0.586 (2) | 0.2049 (6) | 0.101 (2) | 0.338 (7) |
H22D | 0.1894 | 0.5948 | 0.2413 | 0.152* | 0.338 (7) |
H22E | 0.1269 | 0.4888 | 0.1943 | 0.152* | 0.338 (7) |
H22F | 0.0305 | 0.6246 | 0.2090 | 0.152* | 0.338 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.1238 (19) | 0.184 (3) | 0.0495 (10) | −0.031 (2) | −0.0206 (13) | −0.0071 (15) |
F2 | 0.1106 (19) | 0.1178 (18) | 0.115 (2) | −0.0261 (17) | −0.0049 (16) | 0.0635 (17) |
O1 | 0.0911 (15) | 0.0529 (12) | 0.0699 (13) | −0.0167 (12) | −0.0212 (13) | −0.0061 (11) |
O2 | 0.0827 (15) | 0.0703 (13) | 0.0798 (15) | 0.0215 (13) | −0.0310 (13) | −0.0108 (12) |
C1 | 0.074 (2) | 0.114 (3) | 0.0449 (15) | −0.001 (2) | −0.0088 (15) | −0.0080 (18) |
C2 | 0.084 (2) | 0.107 (3) | 0.0504 (17) | −0.017 (2) | 0.0000 (16) | 0.0070 (18) |
C3 | 0.0666 (18) | 0.089 (2) | 0.0507 (15) | −0.0189 (18) | −0.0031 (14) | 0.0025 (16) |
C4 | 0.0518 (13) | 0.0517 (14) | 0.0472 (13) | 0.0015 (12) | −0.0013 (11) | −0.0051 (12) |
C5 | 0.0565 (14) | 0.0635 (17) | 0.0508 (15) | −0.0046 (14) | −0.0029 (12) | −0.0042 (13) |
C6 | 0.0681 (18) | 0.085 (2) | 0.0596 (18) | −0.0133 (18) | −0.0115 (15) | −0.0120 (17) |
C7 | 0.0479 (12) | 0.0482 (13) | 0.0469 (13) | −0.0001 (11) | −0.0008 (11) | −0.0041 (11) |
C8 | 0.0566 (14) | 0.0483 (14) | 0.0522 (14) | 0.0011 (12) | −0.0040 (12) | 0.0003 (12) |
C9 | 0.0550 (13) | 0.0480 (15) | 0.0553 (15) | −0.0007 (12) | −0.0057 (12) | −0.0081 (12) |
C10 | 0.0521 (13) | 0.0463 (13) | 0.0522 (14) | 0.0074 (11) | −0.0063 (11) | −0.0060 (11) |
C11 | 0.0507 (12) | 0.0452 (13) | 0.0495 (13) | 0.0053 (11) | −0.0055 (11) | −0.0033 (11) |
C12 | 0.0523 (13) | 0.0455 (13) | 0.0501 (13) | −0.0040 (12) | −0.0024 (11) | −0.0061 (11) |
C13 | 0.0533 (13) | 0.0534 (14) | 0.0524 (14) | −0.0017 (12) | −0.0082 (12) | 0.0002 (12) |
C14 | 0.0736 (19) | 0.073 (2) | 0.0636 (18) | 0.0121 (18) | 0.0029 (16) | 0.0092 (16) |
C15 | 0.071 (2) | 0.119 (3) | 0.066 (2) | 0.004 (2) | 0.0070 (18) | 0.017 (2) |
C16 | 0.0675 (18) | 0.083 (2) | 0.085 (2) | −0.0157 (19) | −0.0109 (18) | 0.030 (2) |
C17 | 0.089 (2) | 0.0574 (18) | 0.083 (2) | −0.0118 (18) | −0.013 (2) | 0.0115 (17) |
C18 | 0.0804 (19) | 0.0503 (15) | 0.0639 (18) | −0.0037 (15) | −0.0085 (16) | 0.0022 (14) |
C19 | 0.0694 (17) | 0.0488 (15) | 0.0621 (17) | 0.0097 (14) | −0.0164 (14) | −0.0082 (13) |
C20 | 0.084 (2) | 0.0539 (17) | 0.090 (2) | −0.0160 (17) | −0.009 (2) | −0.0042 (17) |
O3 | 0.067 (3) | 0.088 (3) | 0.049 (2) | 0.010 (2) | −0.006 (2) | −0.020 (2) |
C21 | 0.093 (3) | 0.159 (7) | 0.053 (3) | 0.015 (4) | −0.010 (3) | −0.033 (4) |
C22 | 0.229 (13) | 0.114 (7) | 0.142 (9) | −0.014 (8) | −0.090 (9) | −0.010 (6) |
O3X | 0.054 (4) | 0.059 (4) | 0.049 (4) | 0.004 (3) | −0.003 (3) | −0.004 (3) |
C21X | 0.093 (3) | 0.159 (7) | 0.053 (3) | 0.015 (4) | −0.010 (3) | −0.033 (4) |
C22X | 0.093 (3) | 0.159 (7) | 0.053 (3) | 0.015 (4) | −0.010 (3) | −0.033 (4) |
F1—C1 | 1.362 (4) | C14—C15 | 1.3900 |
F2—C16 | 1.325 (3) | C14—H14A | 0.9300 |
O1—C9 | 1.357 (3) | C15—C16 | 1.3900 |
O1—C20 | 1.415 (4) | C15—H15A | 0.9300 |
O2—C19 | 1.191 (4) | C16—C17 | 1.3900 |
C1—C6 | 1.353 (5) | C17—C18 | 1.3900 |
C1—C2 | 1.376 (5) | C17—H17A | 0.9300 |
C2—C3 | 1.383 (5) | C18—H18A | 0.9300 |
C2—H2A | 0.9300 | C19—O3X | 1.320 (9) |
C3—C4 | 1.392 (4) | C19—O3 | 1.377 (5) |
C3—H3A | 0.9300 | C20—H20A | 0.9600 |
C4—C5 | 1.381 (4) | C20—H20B | 0.9600 |
C4—C7 | 1.491 (4) | C20—H20C | 0.9600 |
C5—C6 | 1.385 (4) | O3—C21 | 1.440 (8) |
C5—H5A | 0.9300 | C21—C22 | 1.346 (14) |
C6—H6A | 0.9300 | C21—H21A | 0.9700 |
C7—C12 | 1.375 (4) | C21—H21B | 0.9700 |
C7—C8 | 1.404 (4) | C22—H22A | 0.9600 |
C8—C9 | 1.385 (4) | C22—H22B | 0.9600 |
C8—H8A | 0.9300 | C22—H22C | 0.9600 |
C9—C10 | 1.398 (4) | O3X—C21X | 1.414 (16) |
C10—C11 | 1.390 (4) | C21X—C22X | 1.68 (3) |
C10—C19 | 1.490 (4) | C21X—H21C | 0.9700 |
C11—C12 | 1.396 (4) | C21X—H21D | 0.9700 |
C11—C13 | 1.494 (3) | C22X—H22D | 0.9600 |
C12—H12A | 0.9300 | C22X—H22E | 0.9600 |
C13—C14 | 1.3900 | C22X—H22F | 0.9600 |
C13—C18 | 1.3900 | ||
C9—O1—C20 | 118.0 (2) | C16—C15—C14 | 120.0 |
C6—C1—F1 | 119.2 (3) | C16—C15—H15A | 120.0 |
C6—C1—C2 | 122.8 (3) | C14—C15—H15A | 120.0 |
F1—C1—C2 | 118.0 (3) | F2—C16—C17 | 120.7 (2) |
C1—C2—C3 | 117.6 (3) | F2—C16—C15 | 119.3 (2) |
C1—C2—H2A | 121.2 | C17—C16—C15 | 120.0 |
C3—C2—H2A | 121.2 | C16—C17—C18 | 120.0 |
C2—C3—C4 | 121.5 (3) | C16—C17—H17A | 120.0 |
C2—C3—H3A | 119.3 | C18—C17—H17A | 120.0 |
C4—C3—H3A | 119.3 | C17—C18—C13 | 120.0 |
C5—C4—C3 | 118.4 (3) | C17—C18—H18A | 120.0 |
C5—C4—C7 | 120.3 (3) | C13—C18—H18A | 120.0 |
C3—C4—C7 | 121.3 (3) | O2—C19—O3X | 120.2 (5) |
C6—C5—C4 | 120.7 (3) | O2—C19—O3 | 123.9 (3) |
C6—C5—H5A | 119.6 | O2—C19—C10 | 125.0 (3) |
C4—C5—H5A | 119.6 | O3X—C19—C10 | 110.6 (4) |
C1—C6—C5 | 119.0 (3) | O3—C19—C10 | 110.4 (3) |
C1—C6—H6A | 120.5 | O1—C20—H20A | 109.5 |
C5—C6—H6A | 120.5 | O1—C20—H20B | 109.5 |
C12—C7—C8 | 118.6 (2) | H20A—C20—H20B | 109.5 |
C12—C7—C4 | 121.6 (2) | O1—C20—H20C | 109.5 |
C8—C7—C4 | 119.7 (2) | H20A—C20—H20C | 109.5 |
C9—C8—C7 | 120.3 (3) | H20B—C20—H20C | 109.5 |
C9—C8—H8A | 119.9 | C19—O3—C21 | 117.4 (5) |
C7—C8—H8A | 119.9 | C22—C21—O3 | 115.7 (10) |
O1—C9—C8 | 124.6 (3) | C22—C21—H21A | 108.4 |
O1—C9—C10 | 114.9 (2) | O3—C21—H21A | 108.4 |
C8—C9—C10 | 120.5 (3) | C22—C21—H21B | 108.4 |
C11—C10—C9 | 119.3 (2) | O3—C21—H21B | 108.4 |
C11—C10—C19 | 122.0 (2) | H21A—C21—H21B | 107.4 |
C9—C10—C19 | 118.7 (2) | C19—O3X—C21X | 115.5 (10) |
C10—C11—C12 | 119.5 (2) | O3X—C21X—C22X | 104.7 (15) |
C10—C11—C13 | 121.6 (2) | O3X—C21X—H21C | 110.8 |
C12—C11—C13 | 118.9 (2) | C22X—C21X—H21C | 110.8 |
C7—C12—C11 | 121.7 (2) | O3X—C21X—H21D | 110.8 |
C7—C12—H12A | 119.2 | C22X—C21X—H21D | 110.8 |
C11—C12—H12A | 119.2 | H21C—C21X—H21D | 108.9 |
C14—C13—C18 | 120.0 | C21X—C22X—H22D | 109.5 |
C14—C13—C11 | 120.24 (15) | C21X—C22X—H22E | 109.5 |
C18—C13—C11 | 119.72 (15) | H22D—C22X—H22E | 109.5 |
C13—C14—C15 | 120.0 | C21X—C22X—H22F | 109.5 |
C13—C14—H14A | 120.0 | H22D—C22X—H22F | 109.5 |
C15—C14—H14A | 120.0 | H22E—C22X—H22F | 109.5 |
C6—C1—C2—C3 | −0.5 (6) | C10—C11—C12—C7 | −2.1 (4) |
F1—C1—C2—C3 | 179.9 (4) | C13—C11—C12—C7 | 176.5 (2) |
C1—C2—C3—C4 | −0.4 (6) | C10—C11—C13—C14 | 55.1 (3) |
C2—C3—C4—C5 | 1.1 (5) | C12—C11—C13—C14 | −123.4 (2) |
C2—C3—C4—C7 | −178.7 (3) | C10—C11—C13—C18 | −127.1 (2) |
C3—C4—C5—C6 | −0.8 (5) | C12—C11—C13—C18 | 54.4 (3) |
C7—C4—C5—C6 | 178.9 (3) | C18—C13—C14—C15 | 0.0 |
F1—C1—C6—C5 | −179.6 (4) | C11—C13—C14—C15 | 177.8 (2) |
C2—C1—C6—C5 | 0.7 (6) | C13—C14—C15—C16 | 0.0 |
C4—C5—C6—C1 | −0.1 (6) | C14—C15—C16—F2 | 179.1 (2) |
C5—C4—C7—C12 | 26.1 (4) | C14—C15—C16—C17 | 0.0 |
C3—C4—C7—C12 | −154.1 (3) | F2—C16—C17—C18 | −179.1 (2) |
C5—C4—C7—C8 | −153.1 (3) | C15—C16—C17—C18 | 0.0 |
C3—C4—C7—C8 | 26.6 (4) | C16—C17—C18—C13 | 0.0 |
C12—C7—C8—C9 | 1.7 (4) | C14—C13—C18—C17 | 0.0 |
C4—C7—C8—C9 | −179.0 (2) | C11—C13—C18—C17 | −177.8 (2) |
C20—O1—C9—C8 | −2.3 (5) | C11—C10—C19—O2 | 70.4 (4) |
C20—O1—C9—C10 | 177.3 (3) | C9—C10—C19—O2 | −107.4 (4) |
C7—C8—C9—O1 | 178.1 (3) | C11—C10—C19—O3X | −132.9 (5) |
C7—C8—C9—C10 | −1.5 (4) | C9—C10—C19—O3X | 49.3 (6) |
O1—C9—C10—C11 | 179.9 (2) | C11—C10—C19—O3 | −100.0 (4) |
C8—C9—C10—C11 | −0.4 (4) | C9—C10—C19—O3 | 82.2 (4) |
O1—C9—C10—C19 | −2.2 (4) | O2—C19—O3—C21 | 8.6 (9) |
C8—C9—C10—C19 | 177.4 (3) | O3X—C19—O3—C21 | −84.6 (11) |
C9—C10—C11—C12 | 2.2 (4) | C10—C19—O3—C21 | 179.1 (6) |
C19—C10—C11—C12 | −175.6 (3) | C19—O3—C21—C22 | 83.5 (10) |
C9—C10—C11—C13 | −176.3 (2) | O2—C19—O3X—C21X | −13.1 (13) |
C19—C10—C11—C13 | 5.9 (4) | O3—C19—O3X—C21X | 93.4 (14) |
C8—C7—C12—C11 | 0.1 (4) | C10—C19—O3X—C21X | −171.1 (10) |
C4—C7—C12—C11 | −179.2 (2) | C19—O3X—C21X—C22X | −79.9 (12) |
Cg2 and Cg3 are the centroids of the C7–C12 and C13–C18 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···O2i | 0.93 | 2.59 | 3.515 (3) | 179 |
C5—H5A···Cg3ii | 0.93 | 2.92 | 3.589 (3) | 130 |
C20—H20A···Cg2iii | 0.96 | 2.83 | 3.710 (4) | 152 |
Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) −x−1, y+1/2, −z+1/2; (iii) −x, y+3/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H18F2O3 |
Mr | 368.36 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 8.5197 (11), 9.5225 (12), 22.871 (3) |
V (Å3) | 1855.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.43 × 0.21 × 0.15 |
Data collection | |
Diffractometer | Bruker APEX DUO CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.958, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11701, 3036, 2131 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.171, 1.10 |
No. of reflections | 3036 |
No. of parameters | 251 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.23 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg2 and Cg3 are the centroids of the C7–C12 and C13–C18 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···O2i | 0.93 | 2.59 | 3.515 (3) | 178.8 |
C5—H5A···Cg3ii | 0.93 | 2.92 | 3.589 (3) | 130 |
C20—H20A···Cg2iii | 0.96 | 2.83 | 3.710 (4) | 152 |
Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) −x−1, y+1/2, −z+1/2; (iii) −x, y+3/2, −z+1/2. |
Footnotes
‡Thomson Reuters ResearcherID: A-3561-2009.
Acknowledgements
HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PSKBP/8630013). BN thanks the UGC for financial assistance through the SAP and BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for research facilities.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3390. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kotnis, A. S. (1990). Tetrahedron Lett. 31, 481–484. CrossRef CAS Web of Science Google Scholar
Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Molbank, M745. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
In continuation of our work on the synthesis of terphenyl esters (Fun et al., 2011; Samshuddin et al., 2011), the title compound was prepared and its crystal structure is reported. The starting material of the title compound was prepared from 4,4'-difluoro chalcone by several steps.
The molecular structure of the title compound is shown in Fig. 1. The mean planes of the two fluoro-substituted phenyl rings (C1–C6 and C13–C18) make dihedral angles of 25.89 (15) and 55.00 (12)°, respectively, with the mean plane of the central benzene ring (C7–C12) in the terphenyl moiety. The ethoxy group (O3/C21/C22) is disordered over two positions with a site-occupancy ratio of 0.662 (7):0.338 (7). Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those observed in a related structure (Fun et al., 2011).
In the crystal structure (Fig. 2), the molecules are interconnected by C12—H12A···O2 hydrogen bonds (Table 1) into chains along the a axis. The crystal structure is further stabilized by C—H···π interactions (Table 1). π—π interactions are also observed with Cg2···Cg3 distance = 3.8605 (15) Å (symmetry code: 1/2+x,1/2-y,-z; Cg2 and Cg3 are the centroids of the C7–C12 and C13—C18 rings, respectively).