Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 3| March 2014| Page o244
doi:10.1107/S1600536814001871

4-Cyano-3-fluoro­phenyl 4-(hexa­dec­yl­­oxy)benzoate

M. K. Usha,a H. T. Srinivas,b Rajni Kant,c Vivek K. Guptac and D. Revannasiddaiaha*

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

(Received 8 January 2014; accepted 27 January 2014; online 5 February 2014)

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[Chigrinov, V. G., Kozenkov, V. M. & Kwok, H. S. (2008). In Wiley-SID series in Display Technology. Weinheim: John Wiley & Sons.]); Reddy & Tschierske (2006[Reddy, A. & Tschierske, C. (2006). J. Mater. Chem. 16, 907-961.]); Hird & Toyne (1998[Hird, M. & Toyne, K. J. (1998). Mol. Cryst. Liq. Cryst. 323, 1-67.]); Roussel (1999[Roussel, F. (1999). Liq. Cryst. 26, 251-260.]). For a related structure, see: Al-Eryani et al. (2011[Al-Eryani, W. F. A., Srinivasa, H. T., Jeyaseelan, S., Sadashivaiah, T. & Devarajegowda, H. C. (2011). Acta Cryst. E67, o840.]).

[Scheme 1]

Experimental

Crystal data

  • C30H40FNO3

  • Mr = 481.63

  • Monoclinic, P 21 /c

  • a = 22.937 (3) Å

  • b = 9.2022 (9) Å

  • c = 13.2859 (10) Å

  • β = 100.749 (8)°

  • V = 2755.1 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm
Data collection

  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.596, Tmax = 0.985

  • 10771 measured reflections

  • 5379 independent reflections

  • 2448 reflections with I > 2σ(I)

  • Rint = 0.047
Refinement

  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.146

  • S = 0.96

  • 5379 reflections

  • 318 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.12 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 983658

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814001871/is5333sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814001871/is5333Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814001871/is5333Isup3.cml

checkCIF report


Comment top

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).

Related literature top

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 top

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 column chromatography using silica gel (60–120 mesh) with 5% dichloromethane-hexane as eluent. 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): 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).

Refinement top

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).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. ORTEP diagram of the title compound with 50% probability ellipsoids.
[Figure 2] Fig. 2. The packing arrangement of molecules viewed along the b axis. H atoms have been omitted for clarity
4-Cyano-3-fluorophenyl 4-(hexadecyloxy)benzoate top
Crystal data top
C30H40FNO3F(000) = 1040
Mr = 481.63Dx = 1.161 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2658 reflections
a = 22.937 (3) Åθ = 3.9–28.9°
b = 9.2022 (9) ŵ = 0.08 mm−1
c = 13.2859 (10) ÅT = 293 K
β = 100.749 (8)°Block, white
V = 2755.1 (5) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer		5379 independent reflections
Radiation source: fine-focus sealed tube2448 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 16.1049 pixels mm-1θmax = 26.0°, θmin = 3.6°
ω scansh = −28→27
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		k = −11→10
Tmin = 0.596, Tmax = 0.985l = −15→16
10771 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-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 reflectionsΔρmax = 0.18 e Å−3
318 parametersΔρmin = −0.12 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (4)
Crystal data top
C30H40FNO3V = 2755.1 (5) Å3
Mr = 481.63Z = 4
Monoclinic, P21/cMo Kα radiation
a = 22.937 (3) ŵ = 0.08 mm−1
b = 9.2022 (9) ÅT = 293 K
c = 13.2859 (10) Å0.30 × 0.20 × 0.20 mm
β = 100.749 (8)°
Data collection top
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 = 0.985Rint = 0.047
10771 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 0.96Δρmax = 0.18 e Å−3
5379 reflectionsΔρmin = −0.12 e Å−3
318 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F30.01653 (7)0.95837 (17)−0.72555 (9)0.0945 (7)
O90.08886 (8)0.82686 (18)−0.37972 (10)0.0720 (7)
O100.11933 (8)0.59458 (19)−0.37524 (11)0.0774 (7)
O170.25399 (8)0.84443 (17)0.05228 (10)0.0698 (6)
N8−0.10909 (11)0.7467 (3)−0.81803 (16)0.0974 (11)
C10.04873 (11)0.8036 (3)−0.47032 (16)0.0588 (9)
C20.05447 (11)0.8891 (3)−0.55275 (16)0.0643 (10)
C30.01283 (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)
C60.00309 (12)0.7071 (3)−0.47546 (17)0.0712 (11)
C7−0.07573 (12)0.7596 (3)−0.74352 (18)0.0699 (10)
C100.12016 (11)0.7104 (3)−0.33365 (16)0.0560 (9)
C110.15403 (10)0.7469 (2)−0.23164 (14)0.0504 (8)
C120.18556 (11)0.6385 (3)−0.17480 (15)0.0602 (9)
C130.21936 (11)0.6657 (2)−0.07876 (15)0.0585 (9)
C140.22127 (11)0.8039 (2)−0.03907 (15)0.0540 (8)
C150.18824 (11)0.9125 (3)−0.09427 (15)0.0694 (10)
C160.15494 (11)0.8840 (3)−0.18988 (15)0.0650 (10)
C180.28506 (11)0.7371 (2)0.11804 (14)0.0562 (9)
C190.32012 (11)0.8146 (2)0.20936 (14)0.0551 (8)
C200.35225 (10)0.7152 (2)0.29200 (14)0.0546 (8)
C210.38807 (11)0.7963 (2)0.38133 (14)0.0546 (9)
C220.42129 (11)0.7045 (2)0.46717 (14)0.0541 (8)
C230.45679 (11)0.7898 (2)0.55487 (14)0.0521 (8)
C240.49090 (10)0.7010 (2)0.64152 (13)0.0531 (8)
C250.52575 (10)0.7893 (2)0.72853 (13)0.0523 (8)
C260.56051 (10)0.7018 (2)0.81627 (14)0.0540 (8)
C270.59459 (10)0.7921 (2)0.90214 (14)0.0543 (8)
C280.62995 (11)0.7061 (2)0.99015 (14)0.0548 (9)
C290.66382 (11)0.7978 (2)1.07614 (14)0.0579 (9)
C300.69986 (11)0.7133 (2)1.16370 (14)0.0600 (9)
C310.73187 (11)0.8036 (2)1.25108 (15)0.0601 (9)
C320.76864 (11)0.7210 (3)1.33800 (15)0.0662 (10)
C330.80091 (12)0.8162 (3)1.42314 (16)0.0834 (11)
H20.085300.95560−0.549000.0770*
H5−0.069000.62510−0.568300.0860*
H6−0.000300.65150−0.418400.0860*
H120.184200.54470−0.201300.0720*
H130.240600.59100−0.041500.0700*
H150.188401.00550−0.066900.0830*
H160.132900.95810−0.226500.0780*
H18A0.311500.683000.082700.0670*
H18B0.257300.669600.139700.0670*
H19A0.293400.876200.238900.0660*
H19B0.349000.877200.186200.0660*
H20A0.323400.654300.316700.0660*
H20B0.378500.652100.262600.0660*
H21A0.416500.857400.355600.0660*
H21B0.361500.860100.409500.0660*
H22A0.448000.640600.439500.0650*
H22B0.393000.643900.493700.0650*
H23A0.484600.851100.527900.0620*
H23B0.429900.853200.582400.0620*
H24A0.518200.638100.614400.0640*
H24B0.463200.639300.668700.0640*
H25A0.498400.852000.755500.0630*
H25B0.553200.851200.701100.0630*
H26A0.533200.639600.843900.0650*
H26B0.588200.639500.789600.0650*
H27A0.566800.854000.928900.0650*
H27B0.621600.854900.874300.0650*
H28A0.603000.643101.018000.0660*
H28B0.657900.644600.963600.0660*
H29A0.690300.861801.047900.0690*
H29B0.635700.858501.103100.0690*
H30A0.673600.646701.190100.0720*
H30B0.728900.655301.137000.0720*
H31A0.757600.871201.224300.0720*
H31B0.702700.860401.278200.0720*
H32A0.797600.663001.311200.0790*
H32B0.743000.654901.366300.0790*
H33A0.827600.879601.396500.1250*
H33B0.823000.756401.476100.1250*
H33C0.772600.873301.450900.1250*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F30.1042 (14)0.1239 (13)0.0487 (8)−0.0370 (11)−0.0027 (7)0.0190 (8)
O90.0806 (14)0.0730 (11)0.0487 (9)−0.0020 (10)−0.0230 (8)−0.0015 (8)
O100.0708 (14)0.0826 (13)0.0679 (11)0.0087 (11)−0.0152 (9)−0.0231 (9)
O170.0810 (14)0.0649 (10)0.0495 (9)0.0109 (10)−0.0241 (8)−0.0055 (8)
N80.088 (2)0.113 (2)0.0735 (15)0.0049 (17)−0.0308 (13)−0.0068 (14)
C10.0608 (18)0.0662 (16)0.0429 (13)0.0007 (14)−0.0068 (11)−0.0036 (12)
C20.0612 (18)0.0727 (18)0.0522 (14)−0.0081 (14)−0.0068 (12)−0.0039 (12)
C30.0663 (19)0.0713 (17)0.0440 (14)−0.0041 (15)−0.0018 (12)0.0036 (12)
C40.0539 (17)0.0689 (17)0.0449 (14)0.0024 (14)−0.0097 (11)−0.0017 (12)
C50.0604 (19)0.0788 (19)0.0674 (16)−0.0109 (15)−0.0075 (13)0.0036 (14)
C60.068 (2)0.084 (2)0.0562 (16)−0.0095 (17)−0.0024 (13)0.0126 (13)
C70.066 (2)0.0752 (18)0.0602 (16)0.0038 (15)−0.0095 (13)0.0005 (13)
C100.0503 (16)0.0657 (16)0.0479 (14)0.0009 (14)−0.0018 (11)−0.0016 (12)
C110.0476 (15)0.0592 (15)0.0401 (12)−0.0033 (13)−0.0032 (10)−0.0006 (10)
C120.0632 (18)0.0571 (15)0.0538 (14)0.0046 (14)−0.0057 (12)−0.0109 (11)
C130.0615 (18)0.0545 (14)0.0517 (14)0.0057 (13)−0.0097 (12)0.0009 (11)
C140.0558 (16)0.0604 (15)0.0393 (12)0.0032 (13)−0.0081 (11)−0.0006 (11)
C150.089 (2)0.0554 (15)0.0524 (14)0.0084 (15)−0.0160 (13)−0.0069 (11)
C160.0714 (19)0.0585 (16)0.0545 (14)0.0032 (15)−0.0157 (12)0.0017 (12)
C180.0574 (17)0.0617 (15)0.0437 (13)0.0033 (13)−0.0056 (11)−0.0002 (11)
C190.0553 (16)0.0613 (15)0.0433 (12)0.0034 (13)−0.0049 (11)−0.0031 (10)
C200.0601 (17)0.0562 (14)0.0414 (12)0.0014 (13)−0.0062 (11)0.0006 (10)
C210.0573 (17)0.0591 (15)0.0420 (12)0.0000 (13)−0.0050 (11)0.0013 (10)
C220.0601 (17)0.0524 (14)0.0443 (12)0.0026 (13)−0.0045 (11)−0.0014 (10)
C230.0569 (16)0.0528 (14)0.0407 (12)−0.0010 (12)−0.0058 (10)0.0006 (10)
C240.0580 (17)0.0526 (14)0.0430 (12)0.0034 (12)−0.0054 (11)−0.0027 (10)
C250.0555 (16)0.0528 (14)0.0434 (12)−0.0029 (12)−0.0043 (11)0.0007 (10)
C260.0582 (17)0.0554 (14)0.0424 (12)0.0039 (13)−0.0058 (11)−0.0010 (10)
C270.0595 (17)0.0551 (14)0.0417 (12)−0.0017 (13)−0.0076 (11)0.0024 (10)
C280.0586 (17)0.0583 (15)0.0415 (12)0.0015 (13)−0.0062 (11)0.0019 (10)
C290.0602 (17)0.0612 (15)0.0449 (13)−0.0007 (13)−0.0091 (11)0.0027 (11)
C300.0672 (19)0.0622 (16)0.0426 (13)0.0079 (14)−0.0105 (11)−0.0003 (11)
C310.0609 (18)0.0679 (16)0.0457 (13)0.0006 (14)−0.0054 (11)−0.0012 (11)
C320.0667 (19)0.0728 (17)0.0504 (14)0.0111 (15)−0.0114 (12)−0.0042 (12)
C330.084 (2)0.098 (2)0.0563 (15)0.0051 (18)−0.0173 (14)−0.0121 (13)
Geometric parameters (Å, º) top
F3—C31.388 (3)C6—H60.9300
O9—C11.389 (3)C12—H120.9300
O9—C101.369 (3)C13—H130.9300
O10—C101.199 (3)C15—H150.9300
O17—C141.355 (2)C16—H160.9300
O17—C181.419 (2)C18—H18A0.9700
N8—C71.139 (3)C18—H18B0.9700
C1—C21.375 (3)C19—H19A0.9700
C1—C61.365 (4)C19—H19B0.9700
C2—C31.376 (3)C20—H20A0.9700
C3—C41.373 (4)C20—H20B0.9700
C4—C51.390 (3)C21—H21A0.9700
C4—C71.437 (3)C21—H21B0.9700
C5—C61.382 (3)C22—H22A0.9700
C10—C111.470 (3)C22—H22B0.9700
C11—C121.373 (3)C23—H23A0.9700
C11—C161.377 (3)C23—H23B0.9700
C12—C131.387 (3)C24—H24A0.9700
C13—C141.374 (3)C24—H24B0.9700
C14—C151.380 (3)C25—H25A0.9700
C15—C161.380 (3)C25—H25B0.9700
C18—C191.505 (3)C26—H26A0.9700
C19—C201.511 (3)C26—H26B0.9700
C20—C211.509 (3)C27—H27A0.9700
C21—C221.507 (3)C27—H27B0.9700
C22—C231.511 (3)C28—H28A0.9700
C23—C241.506 (3)C28—H28B0.9700
C24—C251.514 (3)C29—H29A0.9700
C25—C261.515 (3)C29—H29B0.9700
C26—C271.507 (3)C30—H30A0.9700
C27—C281.516 (3)C30—H30B0.9700
C28—C291.513 (3)C31—H31A0.9700
C29—C301.511 (3)C31—H31B0.9700
C30—C311.503 (3)C32—H32A0.9700
C31—C321.503 (3)C32—H32B0.9700
C32—C331.511 (3)C33—H33A0.9600
C2—H20.9300C33—H33B0.9600
C5—H50.9300C33—H33C0.9600
C1—O9—C10118.32 (19)C21—C20—H20A109.00
C14—O17—C18119.38 (16)C21—C20—H20B109.00
O9—C1—C2117.1 (2)H20A—C20—H20B108.00
O9—C1—C6121.5 (2)C20—C21—H21A108.00
C2—C1—C6121.3 (2)C20—C21—H21B108.00
C1—C2—C3117.5 (2)C22—C21—H21A108.00
F3—C3—C2119.4 (2)C22—C21—H21B108.00
F3—C3—C4117.56 (19)H21A—C21—H21B107.00
C2—C3—C4123.1 (2)C21—C22—H22A109.00
C3—C4—C5118.0 (2)C21—C22—H22B109.00
C3—C4—C7121.9 (2)C23—C22—H22A109.00
C5—C4—C7120.2 (2)C23—C22—H22B109.00
C4—C5—C6119.7 (2)H22A—C22—H22B108.00
C1—C6—C5120.4 (2)C22—C23—H23A108.00
N8—C7—C4179.3 (3)C22—C23—H23B108.00
O9—C10—O10121.9 (2)C24—C23—H23A108.00
O9—C10—C11112.1 (2)C24—C23—H23B108.00
O10—C10—C11126.0 (2)H23A—C23—H23B107.00
C10—C11—C12118.35 (19)C23—C24—H24A109.00
C10—C11—C16123.1 (2)C23—C24—H24B109.00
C12—C11—C16118.51 (19)C25—C24—H24A109.00
C11—C12—C13121.5 (2)C25—C24—H24B109.00
C12—C13—C14119.5 (2)H24A—C24—H24B108.00
O17—C14—C13124.83 (19)C24—C25—H25A108.00
O17—C14—C15115.74 (18)C24—C25—H25B108.00
C13—C14—C15119.4 (2)C26—C25—H25A108.00
C14—C15—C16120.4 (2)C26—C25—H25B108.00
C11—C16—C15120.6 (2)H25A—C25—H25B107.00
O17—C18—C19107.34 (15)C25—C26—H26A109.00
C18—C19—C20114.45 (16)C25—C26—H26B109.00
C19—C20—C21113.10 (15)C27—C26—H26A109.00
C20—C21—C22116.25 (16)C27—C26—H26B109.00
C21—C22—C23114.59 (16)H26A—C26—H26B108.00
C22—C23—C24115.84 (16)C26—C27—H27A109.00
C23—C24—C25114.68 (15)C26—C27—H27B109.00
C24—C25—C26115.43 (15)C28—C27—H27A109.00
C25—C26—C27114.43 (15)C28—C27—H27B109.00
C26—C27—C28115.06 (16)H27A—C27—H27B107.00
C27—C28—C29114.63 (15)C27—C28—H28A109.00
C28—C29—C30115.12 (16)C27—C28—H28B109.00
C29—C30—C31115.37 (16)C29—C28—H28A109.00
C30—C31—C32115.92 (17)C29—C28—H28B109.00
C31—C32—C33114.1 (2)H28A—C28—H28B108.00
C1—C2—H2121.00C28—C29—H29A108.00
C3—C2—H2121.00C28—C29—H29B108.00
C4—C5—H5120.00C30—C29—H29A109.00
C6—C5—H5120.00C30—C29—H29B109.00
C1—C6—H6120.00H29A—C29—H29B107.00
C5—C6—H6120.00C29—C30—H30A108.00
C11—C12—H12119.00C29—C30—H30B108.00
C13—C12—H12119.00C31—C30—H30A108.00
C12—C13—H13120.00C31—C30—H30B108.00
C14—C13—H13120.00H30A—C30—H30B107.00
C14—C15—H15120.00C30—C31—H31A108.00
C16—C15—H15120.00C30—C31—H31B108.00
C11—C16—H16120.00C32—C31—H31A108.00
C15—C16—H16120.00C32—C31—H31B108.00
O17—C18—H18A110.00H31A—C31—H31B107.00
O17—C18—H18B110.00C31—C32—H32A109.00
C19—C18—H18A110.00C31—C32—H32B109.00
C19—C18—H18B110.00C33—C32—H32A109.00
H18A—C18—H18B109.00C33—C32—H32B109.00
C18—C19—H19A109.00H32A—C32—H32B108.00
C18—C19—H19B109.00C32—C33—H33A109.00
C20—C19—H19A109.00C32—C33—H33B110.00
C20—C19—H19B109.00C32—C33—H33C109.00
H19A—C19—H19B108.00H33A—C33—H33B109.00
C19—C20—H20A109.00H33A—C33—H33C109.00
C19—C20—H20B109.00H33B—C33—H33C110.00
C10—O9—C1—C2−126.7 (3)C10—C11—C12—C13178.8 (2)
C10—O9—C1—C657.7 (3)C16—C11—C12—C13−2.1 (4)
C1—O9—C10—O109.4 (3)C10—C11—C16—C15−179.1 (2)
C1—O9—C10—C11−171.6 (2)C12—C11—C16—C151.9 (4)
C18—O17—C14—C13−5.9 (3)C11—C12—C13—C140.3 (4)
C18—O17—C14—C15174.4 (2)C12—C13—C14—O17−178.0 (2)
C14—O17—C18—C19176.4 (2)C12—C13—C14—C151.7 (4)
O9—C1—C2—C3−176.3 (2)O17—C14—C15—C16177.8 (2)
C6—C1—C2—C3−0.7 (4)C13—C14—C15—C16−2.0 (4)
O9—C1—C6—C5176.6 (2)C14—C15—C16—C110.1 (4)
C2—C1—C6—C51.1 (4)O17—C18—C19—C20175.26 (19)
C1—C2—C3—F3179.1 (2)C18—C19—C20—C21178.7 (2)
C1—C2—C3—C4−0.6 (4)C19—C20—C21—C22179.8 (2)
F3—C3—C4—C5−178.3 (2)C20—C21—C22—C23179.8 (2)
F3—C3—C4—C70.7 (4)C21—C22—C23—C24−179.5 (2)
C2—C3—C4—C51.4 (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—C12177.3 (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—C16177.3 (2)C30—C31—C32—C33178.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O10i0.932.383.237 (3)153
Symmetry code: (i) −x, −y+1, −z−1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O10i0.932.383.237 (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)].

References

First citationAl-Eryani, W. F. A., Srinivasa, H. T., Jeyaseelan, S., Sadashivaiah, T. & Devarajegowda, H. C. (2011). Acta Cryst. E67, o840.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationChigrinov, V. G., Kozenkov, V. M. & Kwok, H. S. (2008). In Wiley-SID series in Display Technology. Weinheim: John Wiley & Sons.  Google Scholar
 First citationHird, M. & Toyne, K. J. (1998). Mol. Cryst. Liq. Cryst. 323, 1–67.  Web of Science CrossRef CAS Google Scholar
 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationOxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationReddy, A. & Tschierske, C. (2006). J. Mater. Chem. 16, 907–961.  Web of Science CrossRef CAS Google Scholar
 First citationRoussel, F. (1999). Liq. Cryst. 26, 251–260.  CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 3| March 2014| Page o244
doi:10.1107/S1600536814001871
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS