organic compounds
4-Cyano-3-fluorophenyl 4-(hexadecyloxy)benzoate
aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, bRaman Research Institute, Bangalore 560 080, India, and cX-ray Crystallography Laboratory, Post Graduate Department of Physics and Electronics, University of Jammu, Jammu Tawi 180 006, India
*Correspondence e-mail: dr@physics.uni-mysore.ac.in
In the title compound, C30H40FNO3, the dihedral angle between the benzene rings is 57.76 (7)°. The alkyl chain adopts an all-trans conformation. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers.
CCDC reference: 983658
Related literature
For general background to the title compound and applications of fluorinated liquid crystals, see: Chigrinov et al. (2008); Reddy & Tschierske (2006); Hird & Toyne (1998); Roussel (1999). For a related structure, see: Al-Eryani et al. (2011).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
CCDC reference: 983658
10.1107/S1600536814001871/is5333sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001871/is5333Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001871/is5333Isup3.cml
A mixture of 2-fluoro-4-hydroxybenzonitrile (0.137 g, 1 equiv), 4-(hexadecyloxy) benzoic acid (0.362 g, 1 equiv) and 4-dimethylamino pyridine (DMAP) catalytic quantity was stirred in dry CH2Cl2. To the above clear solution, N,N-dicyclohexyl carbodiimide (DCC) (0.250 g, 1.2 equiv) was added and stirred for 30 minutes at room temperature. Dicyclohexylurea precipitate was filtered off and washed thoroughly with dry CH2Cl2. The combined filtrates were washed with water and dried over Na2SO4. The crude product was purified by δ (p.p.m.) = 8.11 (m, 2H, Ar—H), 7.69 (m, 1H, Ar—H), 7.19 (m, 2H, Ar—H), 6.98 (m, 2H, Ar—H), 4.05 (t, 2H, –OCH2-, J = 6.55 Hz), 1.83–1.20 (m, 28H, –CH2-), 0.88 (s, 3H, –CH3).
using silica gel (60–120 mesh) with 5% dichloromethane-hexane as The afforded white product was further purified by recrystallization with acetonitrile. This compound is found to exhibit liquid crystalline phase which has been confirmed using optical polarizing microscope and DSC. IR: 2920, 2850, 2233, 1741, 1602, 1454, 1247, 1107, 1045, 844 cm-1; 1H NMR (CDCl3):All the H atoms were positioned geometrically and were refined as riding on their parent C atoms, with C—H distances of 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C) except for the methyl group where Uiso(H) = 1.5Ueq(C).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. ORTEP diagram of the title compound with 50% probability ellipsoids. | |
Fig. 2. The packing arrangement of molecules viewed along the b axis. H atoms have been omitted for clarity |
C30H40FNO3 | F(000) = 1040 |
Mr = 481.63 | Dx = 1.161 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2658 reflections |
a = 22.937 (3) Å | θ = 3.9–28.9° |
b = 9.2022 (9) Å | µ = 0.08 mm−1 |
c = 13.2859 (10) Å | T = 293 K |
β = 100.749 (8)° | Block, white |
V = 2755.1 (5) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 5379 independent reflections |
Radiation source: fine-focus sealed tube | 2448 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 16.1049 pixels mm-1 | θmax = 26.0°, θmin = 3.6° |
ω scans | h = −28→27 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −11→10 |
Tmin = 0.596, Tmax = 0.985 | l = −15→16 |
10771 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.0429P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.001 |
5379 reflections | Δρmax = 0.18 e Å−3 |
318 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0023 (4) |
C30H40FNO3 | V = 2755.1 (5) Å3 |
Mr = 481.63 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 22.937 (3) Å | µ = 0.08 mm−1 |
b = 9.2022 (9) Å | T = 293 K |
c = 13.2859 (10) Å | 0.30 × 0.20 × 0.20 mm |
β = 100.749 (8)° |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 5379 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 2448 reflections with I > 2σ(I) |
Tmin = 0.596, Tmax = 0.985 | Rint = 0.047 |
10771 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.18 e Å−3 |
5379 reflections | Δρmin = −0.12 e Å−3 |
318 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
F3 | 0.01653 (7) | 0.95837 (17) | −0.72555 (9) | 0.0945 (7) | |
O9 | 0.08886 (8) | 0.82686 (18) | −0.37972 (10) | 0.0720 (7) | |
O10 | 0.11933 (8) | 0.59458 (19) | −0.37524 (11) | 0.0774 (7) | |
O17 | 0.25399 (8) | 0.84443 (17) | 0.05228 (10) | 0.0698 (6) | |
N8 | −0.10909 (11) | 0.7467 (3) | −0.81803 (16) | 0.0974 (11) | |
C1 | 0.04873 (11) | 0.8036 (3) | −0.47032 (16) | 0.0588 (9) | |
C2 | 0.05447 (11) | 0.8891 (3) | −0.55275 (16) | 0.0643 (10) | |
C3 | 0.01283 (11) | 0.8727 (3) | −0.64102 (16) | 0.0621 (10) | |
C4 | −0.03311 (11) | 0.7750 (3) | −0.65010 (16) | 0.0583 (9) | |
C5 | −0.03811 (12) | 0.6914 (3) | −0.56497 (17) | 0.0714 (10) | |
C6 | 0.00309 (12) | 0.7071 (3) | −0.47546 (17) | 0.0712 (11) | |
C7 | −0.07573 (12) | 0.7596 (3) | −0.74352 (18) | 0.0699 (10) | |
C10 | 0.12016 (11) | 0.7104 (3) | −0.33365 (16) | 0.0560 (9) | |
C11 | 0.15403 (10) | 0.7469 (2) | −0.23164 (14) | 0.0504 (8) | |
C12 | 0.18556 (11) | 0.6385 (3) | −0.17480 (15) | 0.0602 (9) | |
C13 | 0.21936 (11) | 0.6657 (2) | −0.07876 (15) | 0.0585 (9) | |
C14 | 0.22127 (11) | 0.8039 (2) | −0.03907 (15) | 0.0540 (8) | |
C15 | 0.18824 (11) | 0.9125 (3) | −0.09427 (15) | 0.0694 (10) | |
C16 | 0.15494 (11) | 0.8840 (3) | −0.18988 (15) | 0.0650 (10) | |
C18 | 0.28506 (11) | 0.7371 (2) | 0.11804 (14) | 0.0562 (9) | |
C19 | 0.32012 (11) | 0.8146 (2) | 0.20936 (14) | 0.0551 (8) | |
C20 | 0.35225 (10) | 0.7152 (2) | 0.29200 (14) | 0.0546 (8) | |
C21 | 0.38807 (11) | 0.7963 (2) | 0.38133 (14) | 0.0546 (9) | |
C22 | 0.42129 (11) | 0.7045 (2) | 0.46717 (14) | 0.0541 (8) | |
C23 | 0.45679 (11) | 0.7898 (2) | 0.55487 (14) | 0.0521 (8) | |
C24 | 0.49090 (10) | 0.7010 (2) | 0.64152 (13) | 0.0531 (8) | |
C25 | 0.52575 (10) | 0.7893 (2) | 0.72853 (13) | 0.0523 (8) | |
C26 | 0.56051 (10) | 0.7018 (2) | 0.81627 (14) | 0.0540 (8) | |
C27 | 0.59459 (10) | 0.7921 (2) | 0.90214 (14) | 0.0543 (8) | |
C28 | 0.62995 (11) | 0.7061 (2) | 0.99015 (14) | 0.0548 (9) | |
C29 | 0.66382 (11) | 0.7978 (2) | 1.07614 (14) | 0.0579 (9) | |
C30 | 0.69986 (11) | 0.7133 (2) | 1.16370 (14) | 0.0600 (9) | |
C31 | 0.73187 (11) | 0.8036 (2) | 1.25108 (15) | 0.0601 (9) | |
C32 | 0.76864 (11) | 0.7210 (3) | 1.33800 (15) | 0.0662 (10) | |
C33 | 0.80091 (12) | 0.8162 (3) | 1.42314 (16) | 0.0834 (11) | |
H2 | 0.08530 | 0.95560 | −0.54900 | 0.0770* | |
H5 | −0.06900 | 0.62510 | −0.56830 | 0.0860* | |
H6 | −0.00030 | 0.65150 | −0.41840 | 0.0860* | |
H12 | 0.18420 | 0.54470 | −0.20130 | 0.0720* | |
H13 | 0.24060 | 0.59100 | −0.04150 | 0.0700* | |
H15 | 0.18840 | 1.00550 | −0.06690 | 0.0830* | |
H16 | 0.13290 | 0.95810 | −0.22650 | 0.0780* | |
H18A | 0.31150 | 0.68300 | 0.08270 | 0.0670* | |
H18B | 0.25730 | 0.66960 | 0.13970 | 0.0670* | |
H19A | 0.29340 | 0.87620 | 0.23890 | 0.0660* | |
H19B | 0.34900 | 0.87720 | 0.18620 | 0.0660* | |
H20A | 0.32340 | 0.65430 | 0.31670 | 0.0660* | |
H20B | 0.37850 | 0.65210 | 0.26260 | 0.0660* | |
H21A | 0.41650 | 0.85740 | 0.35560 | 0.0660* | |
H21B | 0.36150 | 0.86010 | 0.40950 | 0.0660* | |
H22A | 0.44800 | 0.64060 | 0.43950 | 0.0650* | |
H22B | 0.39300 | 0.64390 | 0.49370 | 0.0650* | |
H23A | 0.48460 | 0.85110 | 0.52790 | 0.0620* | |
H23B | 0.42990 | 0.85320 | 0.58240 | 0.0620* | |
H24A | 0.51820 | 0.63810 | 0.61440 | 0.0640* | |
H24B | 0.46320 | 0.63930 | 0.66870 | 0.0640* | |
H25A | 0.49840 | 0.85200 | 0.75550 | 0.0630* | |
H25B | 0.55320 | 0.85120 | 0.70110 | 0.0630* | |
H26A | 0.53320 | 0.63960 | 0.84390 | 0.0650* | |
H26B | 0.58820 | 0.63950 | 0.78960 | 0.0650* | |
H27A | 0.56680 | 0.85400 | 0.92890 | 0.0650* | |
H27B | 0.62160 | 0.85490 | 0.87430 | 0.0650* | |
H28A | 0.60300 | 0.64310 | 1.01800 | 0.0660* | |
H28B | 0.65790 | 0.64460 | 0.96360 | 0.0660* | |
H29A | 0.69030 | 0.86180 | 1.04790 | 0.0690* | |
H29B | 0.63570 | 0.85850 | 1.10310 | 0.0690* | |
H30A | 0.67360 | 0.64670 | 1.19010 | 0.0720* | |
H30B | 0.72890 | 0.65530 | 1.13700 | 0.0720* | |
H31A | 0.75760 | 0.87120 | 1.22430 | 0.0720* | |
H31B | 0.70270 | 0.86040 | 1.27820 | 0.0720* | |
H32A | 0.79760 | 0.66300 | 1.31120 | 0.0790* | |
H32B | 0.74300 | 0.65490 | 1.36630 | 0.0790* | |
H33A | 0.82760 | 0.87960 | 1.39650 | 0.1250* | |
H33B | 0.82300 | 0.75640 | 1.47610 | 0.1250* | |
H33C | 0.77260 | 0.87330 | 1.45090 | 0.1250* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F3 | 0.1042 (14) | 0.1239 (13) | 0.0487 (8) | −0.0370 (11) | −0.0027 (7) | 0.0190 (8) |
O9 | 0.0806 (14) | 0.0730 (11) | 0.0487 (9) | −0.0020 (10) | −0.0230 (8) | −0.0015 (8) |
O10 | 0.0708 (14) | 0.0826 (13) | 0.0679 (11) | 0.0087 (11) | −0.0152 (9) | −0.0231 (9) |
O17 | 0.0810 (14) | 0.0649 (10) | 0.0495 (9) | 0.0109 (10) | −0.0241 (8) | −0.0055 (8) |
N8 | 0.088 (2) | 0.113 (2) | 0.0735 (15) | 0.0049 (17) | −0.0308 (13) | −0.0068 (14) |
C1 | 0.0608 (18) | 0.0662 (16) | 0.0429 (13) | 0.0007 (14) | −0.0068 (11) | −0.0036 (12) |
C2 | 0.0612 (18) | 0.0727 (18) | 0.0522 (14) | −0.0081 (14) | −0.0068 (12) | −0.0039 (12) |
C3 | 0.0663 (19) | 0.0713 (17) | 0.0440 (14) | −0.0041 (15) | −0.0018 (12) | 0.0036 (12) |
C4 | 0.0539 (17) | 0.0689 (17) | 0.0449 (14) | 0.0024 (14) | −0.0097 (11) | −0.0017 (12) |
C5 | 0.0604 (19) | 0.0788 (19) | 0.0674 (16) | −0.0109 (15) | −0.0075 (13) | 0.0036 (14) |
C6 | 0.068 (2) | 0.084 (2) | 0.0562 (16) | −0.0095 (17) | −0.0024 (13) | 0.0126 (13) |
C7 | 0.066 (2) | 0.0752 (18) | 0.0602 (16) | 0.0038 (15) | −0.0095 (13) | 0.0005 (13) |
C10 | 0.0503 (16) | 0.0657 (16) | 0.0479 (14) | 0.0009 (14) | −0.0018 (11) | −0.0016 (12) |
C11 | 0.0476 (15) | 0.0592 (15) | 0.0401 (12) | −0.0033 (13) | −0.0032 (10) | −0.0006 (10) |
C12 | 0.0632 (18) | 0.0571 (15) | 0.0538 (14) | 0.0046 (14) | −0.0057 (12) | −0.0109 (11) |
C13 | 0.0615 (18) | 0.0545 (14) | 0.0517 (14) | 0.0057 (13) | −0.0097 (12) | 0.0009 (11) |
C14 | 0.0558 (16) | 0.0604 (15) | 0.0393 (12) | 0.0032 (13) | −0.0081 (11) | −0.0006 (11) |
C15 | 0.089 (2) | 0.0554 (15) | 0.0524 (14) | 0.0084 (15) | −0.0160 (13) | −0.0069 (11) |
C16 | 0.0714 (19) | 0.0585 (16) | 0.0545 (14) | 0.0032 (15) | −0.0157 (12) | 0.0017 (12) |
C18 | 0.0574 (17) | 0.0617 (15) | 0.0437 (13) | 0.0033 (13) | −0.0056 (11) | −0.0002 (11) |
C19 | 0.0553 (16) | 0.0613 (15) | 0.0433 (12) | 0.0034 (13) | −0.0049 (11) | −0.0031 (10) |
C20 | 0.0601 (17) | 0.0562 (14) | 0.0414 (12) | 0.0014 (13) | −0.0062 (11) | 0.0006 (10) |
C21 | 0.0573 (17) | 0.0591 (15) | 0.0420 (12) | 0.0000 (13) | −0.0050 (11) | 0.0013 (10) |
C22 | 0.0601 (17) | 0.0524 (14) | 0.0443 (12) | 0.0026 (13) | −0.0045 (11) | −0.0014 (10) |
C23 | 0.0569 (16) | 0.0528 (14) | 0.0407 (12) | −0.0010 (12) | −0.0058 (10) | 0.0006 (10) |
C24 | 0.0580 (17) | 0.0526 (14) | 0.0430 (12) | 0.0034 (12) | −0.0054 (11) | −0.0027 (10) |
C25 | 0.0555 (16) | 0.0528 (14) | 0.0434 (12) | −0.0029 (12) | −0.0043 (11) | 0.0007 (10) |
C26 | 0.0582 (17) | 0.0554 (14) | 0.0424 (12) | 0.0039 (13) | −0.0058 (11) | −0.0010 (10) |
C27 | 0.0595 (17) | 0.0551 (14) | 0.0417 (12) | −0.0017 (13) | −0.0076 (11) | 0.0024 (10) |
C28 | 0.0586 (17) | 0.0583 (15) | 0.0415 (12) | 0.0015 (13) | −0.0062 (11) | 0.0019 (10) |
C29 | 0.0602 (17) | 0.0612 (15) | 0.0449 (13) | −0.0007 (13) | −0.0091 (11) | 0.0027 (11) |
C30 | 0.0672 (19) | 0.0622 (16) | 0.0426 (13) | 0.0079 (14) | −0.0105 (11) | −0.0003 (11) |
C31 | 0.0609 (18) | 0.0679 (16) | 0.0457 (13) | 0.0006 (14) | −0.0054 (11) | −0.0012 (11) |
C32 | 0.0667 (19) | 0.0728 (17) | 0.0504 (14) | 0.0111 (15) | −0.0114 (12) | −0.0042 (12) |
C33 | 0.084 (2) | 0.098 (2) | 0.0563 (15) | 0.0051 (18) | −0.0173 (14) | −0.0121 (13) |
F3—C3 | 1.388 (3) | C6—H6 | 0.9300 |
O9—C1 | 1.389 (3) | C12—H12 | 0.9300 |
O9—C10 | 1.369 (3) | C13—H13 | 0.9300 |
O10—C10 | 1.199 (3) | C15—H15 | 0.9300 |
O17—C14 | 1.355 (2) | C16—H16 | 0.9300 |
O17—C18 | 1.419 (2) | C18—H18A | 0.9700 |
N8—C7 | 1.139 (3) | C18—H18B | 0.9700 |
C1—C2 | 1.375 (3) | C19—H19A | 0.9700 |
C1—C6 | 1.365 (4) | C19—H19B | 0.9700 |
C2—C3 | 1.376 (3) | C20—H20A | 0.9700 |
C3—C4 | 1.373 (4) | C20—H20B | 0.9700 |
C4—C5 | 1.390 (3) | C21—H21A | 0.9700 |
C4—C7 | 1.437 (3) | C21—H21B | 0.9700 |
C5—C6 | 1.382 (3) | C22—H22A | 0.9700 |
C10—C11 | 1.470 (3) | C22—H22B | 0.9700 |
C11—C12 | 1.373 (3) | C23—H23A | 0.9700 |
C11—C16 | 1.377 (3) | C23—H23B | 0.9700 |
C12—C13 | 1.387 (3) | C24—H24A | 0.9700 |
C13—C14 | 1.374 (3) | C24—H24B | 0.9700 |
C14—C15 | 1.380 (3) | C25—H25A | 0.9700 |
C15—C16 | 1.380 (3) | C25—H25B | 0.9700 |
C18—C19 | 1.505 (3) | C26—H26A | 0.9700 |
C19—C20 | 1.511 (3) | C26—H26B | 0.9700 |
C20—C21 | 1.509 (3) | C27—H27A | 0.9700 |
C21—C22 | 1.507 (3) | C27—H27B | 0.9700 |
C22—C23 | 1.511 (3) | C28—H28A | 0.9700 |
C23—C24 | 1.506 (3) | C28—H28B | 0.9700 |
C24—C25 | 1.514 (3) | C29—H29A | 0.9700 |
C25—C26 | 1.515 (3) | C29—H29B | 0.9700 |
C26—C27 | 1.507 (3) | C30—H30A | 0.9700 |
C27—C28 | 1.516 (3) | C30—H30B | 0.9700 |
C28—C29 | 1.513 (3) | C31—H31A | 0.9700 |
C29—C30 | 1.511 (3) | C31—H31B | 0.9700 |
C30—C31 | 1.503 (3) | C32—H32A | 0.9700 |
C31—C32 | 1.503 (3) | C32—H32B | 0.9700 |
C32—C33 | 1.511 (3) | C33—H33A | 0.9600 |
C2—H2 | 0.9300 | C33—H33B | 0.9600 |
C5—H5 | 0.9300 | C33—H33C | 0.9600 |
C1—O9—C10 | 118.32 (19) | C21—C20—H20A | 109.00 |
C14—O17—C18 | 119.38 (16) | C21—C20—H20B | 109.00 |
O9—C1—C2 | 117.1 (2) | H20A—C20—H20B | 108.00 |
O9—C1—C6 | 121.5 (2) | C20—C21—H21A | 108.00 |
C2—C1—C6 | 121.3 (2) | C20—C21—H21B | 108.00 |
C1—C2—C3 | 117.5 (2) | C22—C21—H21A | 108.00 |
F3—C3—C2 | 119.4 (2) | C22—C21—H21B | 108.00 |
F3—C3—C4 | 117.56 (19) | H21A—C21—H21B | 107.00 |
C2—C3—C4 | 123.1 (2) | C21—C22—H22A | 109.00 |
C3—C4—C5 | 118.0 (2) | C21—C22—H22B | 109.00 |
C3—C4—C7 | 121.9 (2) | C23—C22—H22A | 109.00 |
C5—C4—C7 | 120.2 (2) | C23—C22—H22B | 109.00 |
C4—C5—C6 | 119.7 (2) | H22A—C22—H22B | 108.00 |
C1—C6—C5 | 120.4 (2) | C22—C23—H23A | 108.00 |
N8—C7—C4 | 179.3 (3) | C22—C23—H23B | 108.00 |
O9—C10—O10 | 121.9 (2) | C24—C23—H23A | 108.00 |
O9—C10—C11 | 112.1 (2) | C24—C23—H23B | 108.00 |
O10—C10—C11 | 126.0 (2) | H23A—C23—H23B | 107.00 |
C10—C11—C12 | 118.35 (19) | C23—C24—H24A | 109.00 |
C10—C11—C16 | 123.1 (2) | C23—C24—H24B | 109.00 |
C12—C11—C16 | 118.51 (19) | C25—C24—H24A | 109.00 |
C11—C12—C13 | 121.5 (2) | C25—C24—H24B | 109.00 |
C12—C13—C14 | 119.5 (2) | H24A—C24—H24B | 108.00 |
O17—C14—C13 | 124.83 (19) | C24—C25—H25A | 108.00 |
O17—C14—C15 | 115.74 (18) | C24—C25—H25B | 108.00 |
C13—C14—C15 | 119.4 (2) | C26—C25—H25A | 108.00 |
C14—C15—C16 | 120.4 (2) | C26—C25—H25B | 108.00 |
C11—C16—C15 | 120.6 (2) | H25A—C25—H25B | 107.00 |
O17—C18—C19 | 107.34 (15) | C25—C26—H26A | 109.00 |
C18—C19—C20 | 114.45 (16) | C25—C26—H26B | 109.00 |
C19—C20—C21 | 113.10 (15) | C27—C26—H26A | 109.00 |
C20—C21—C22 | 116.25 (16) | C27—C26—H26B | 109.00 |
C21—C22—C23 | 114.59 (16) | H26A—C26—H26B | 108.00 |
C22—C23—C24 | 115.84 (16) | C26—C27—H27A | 109.00 |
C23—C24—C25 | 114.68 (15) | C26—C27—H27B | 109.00 |
C24—C25—C26 | 115.43 (15) | C28—C27—H27A | 109.00 |
C25—C26—C27 | 114.43 (15) | C28—C27—H27B | 109.00 |
C26—C27—C28 | 115.06 (16) | H27A—C27—H27B | 107.00 |
C27—C28—C29 | 114.63 (15) | C27—C28—H28A | 109.00 |
C28—C29—C30 | 115.12 (16) | C27—C28—H28B | 109.00 |
C29—C30—C31 | 115.37 (16) | C29—C28—H28A | 109.00 |
C30—C31—C32 | 115.92 (17) | C29—C28—H28B | 109.00 |
C31—C32—C33 | 114.1 (2) | H28A—C28—H28B | 108.00 |
C1—C2—H2 | 121.00 | C28—C29—H29A | 108.00 |
C3—C2—H2 | 121.00 | C28—C29—H29B | 108.00 |
C4—C5—H5 | 120.00 | C30—C29—H29A | 109.00 |
C6—C5—H5 | 120.00 | C30—C29—H29B | 109.00 |
C1—C6—H6 | 120.00 | H29A—C29—H29B | 107.00 |
C5—C6—H6 | 120.00 | C29—C30—H30A | 108.00 |
C11—C12—H12 | 119.00 | C29—C30—H30B | 108.00 |
C13—C12—H12 | 119.00 | C31—C30—H30A | 108.00 |
C12—C13—H13 | 120.00 | C31—C30—H30B | 108.00 |
C14—C13—H13 | 120.00 | H30A—C30—H30B | 107.00 |
C14—C15—H15 | 120.00 | C30—C31—H31A | 108.00 |
C16—C15—H15 | 120.00 | C30—C31—H31B | 108.00 |
C11—C16—H16 | 120.00 | C32—C31—H31A | 108.00 |
C15—C16—H16 | 120.00 | C32—C31—H31B | 108.00 |
O17—C18—H18A | 110.00 | H31A—C31—H31B | 107.00 |
O17—C18—H18B | 110.00 | C31—C32—H32A | 109.00 |
C19—C18—H18A | 110.00 | C31—C32—H32B | 109.00 |
C19—C18—H18B | 110.00 | C33—C32—H32A | 109.00 |
H18A—C18—H18B | 109.00 | C33—C32—H32B | 109.00 |
C18—C19—H19A | 109.00 | H32A—C32—H32B | 108.00 |
C18—C19—H19B | 109.00 | C32—C33—H33A | 109.00 |
C20—C19—H19A | 109.00 | C32—C33—H33B | 110.00 |
C20—C19—H19B | 109.00 | C32—C33—H33C | 109.00 |
H19A—C19—H19B | 108.00 | H33A—C33—H33B | 109.00 |
C19—C20—H20A | 109.00 | H33A—C33—H33C | 109.00 |
C19—C20—H20B | 109.00 | H33B—C33—H33C | 110.00 |
C10—O9—C1—C2 | −126.7 (3) | C10—C11—C12—C13 | 178.8 (2) |
C10—O9—C1—C6 | 57.7 (3) | C16—C11—C12—C13 | −2.1 (4) |
C1—O9—C10—O10 | 9.4 (3) | C10—C11—C16—C15 | −179.1 (2) |
C1—O9—C10—C11 | −171.6 (2) | C12—C11—C16—C15 | 1.9 (4) |
C18—O17—C14—C13 | −5.9 (3) | C11—C12—C13—C14 | 0.3 (4) |
C18—O17—C14—C15 | 174.4 (2) | C12—C13—C14—O17 | −178.0 (2) |
C14—O17—C18—C19 | 176.4 (2) | C12—C13—C14—C15 | 1.7 (4) |
O9—C1—C2—C3 | −176.3 (2) | O17—C14—C15—C16 | 177.8 (2) |
C6—C1—C2—C3 | −0.7 (4) | C13—C14—C15—C16 | −2.0 (4) |
O9—C1—C6—C5 | 176.6 (2) | C14—C15—C16—C11 | 0.1 (4) |
C2—C1—C6—C5 | 1.1 (4) | O17—C18—C19—C20 | 175.26 (19) |
C1—C2—C3—F3 | 179.1 (2) | C18—C19—C20—C21 | 178.7 (2) |
C1—C2—C3—C4 | −0.6 (4) | C19—C20—C21—C22 | 179.8 (2) |
F3—C3—C4—C5 | −178.3 (2) | C20—C21—C22—C23 | 179.8 (2) |
F3—C3—C4—C7 | 0.7 (4) | C21—C22—C23—C24 | −179.5 (2) |
C2—C3—C4—C5 | 1.4 (4) | C22—C23—C24—C25 | −179.67 (19) |
C2—C3—C4—C7 | −179.6 (3) | C23—C24—C25—C26 | −179.82 (19) |
C3—C4—C5—C6 | −0.9 (4) | C24—C25—C26—C27 | −179.73 (19) |
C7—C4—C5—C6 | −180.0 (2) | C25—C26—C27—C28 | −179.58 (19) |
C4—C5—C6—C1 | −0.3 (4) | C26—C27—C28—C29 | −179.8 (2) |
O9—C10—C11—C12 | 177.3 (2) | C27—C28—C29—C30 | −179.3 (2) |
O9—C10—C11—C16 | −1.7 (3) | C28—C29—C30—C31 | −177.9 (2) |
O10—C10—C11—C12 | −3.7 (4) | C29—C30—C31—C32 | −179.1 (2) |
O10—C10—C11—C16 | 177.3 (2) | C30—C31—C32—C33 | 178.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O10i | 0.93 | 2.38 | 3.237 (3) | 153 |
Symmetry code: (i) −x, −y+1, −z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O10i | 0.93 | 2.38 | 3.237 (3) | 153 |
Symmetry code: (i) −x, −y+1, −z−1. |
Acknowledgements
MKU thanks the DST, New Delhi, for the award of an INSPIRE Fellowship. RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. VKG is thankful to the University of Jammu, Jammu, India, for financial support. DR acknowledges the UGC for financial support under the Major Research Project scheme [No. F.41–882/2012(SR)].
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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.
Low molar mass liquid crystals possessing low melting temperatures with good thermal range of liquid crystalline phase are in great demand for their potential applications such as, electro-optic display devices, optical switches, semiconductors, light modulators, electrically switchable color-tunable reflectors (Chigrinov et al., 2008; Reddy & Tschierske, 2006). Partially fluorinated liquid crystals, owing to their low viscosity, high chemical and photochemical stability, high resistivity and positive dielectric anisotropy (generated by the high polarity of the C—F bond) are highly suited for the construction of active matrix thin film transistor (TFT) displays (Hird & Toyne, 1998; Roussel, 1999). With this background, we have synthesized the title compound, a novel low molar mass and fluorinated liquid crystal and herewith we report its crystal structure.
The ORTEP diagram of the title compound is shown (Fig. 1). The geometry of the molecule is similar to related structure of 4-(benzyloxy)phenyl 4-hexadecyloxy-3-methoxybenzoate (Al-Eryani et al., 2011). In the title compound, the two benzene rings make a dihedral angle of 57.76 (7)°. An intermolecular C—H···O hydrogen bond (Table 1) links the molecules into a dimer (Fig. 2).