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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 4| April 2013| Pages o621-o622

4-(Dec­yl­oxy)phenyl 2-oxo-7-tri­fluoro­methyl-2H-chromene-3-carboxyl­ate

aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore, Karnataka 570 005, India, bRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore, Karnataka, India, cCenter for Advanced Materials and Department of Chemistry, Tumkur University, Tumkur, Karnataka 572103, India, and dSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India
*Correspondence e-mail: spal12pm@gmail.com

(Received 19 March 2013; accepted 25 March 2013; online 28 March 2013)

The title compound, C27H29F3O5, is a liquid crystal (LC) and exhibits enanti­otropic SmA phase transitions. In the crystal, the dihedral angle between the 2H-chromene ring system and the benzene ring is 62.97 (2)°. The three F atoms of the –CF3 group are disordered over two sets of sites with occupancy factors 0.71 (4):0.29 (4). In the crystal, pairs of C—H⋯O hydrogen bonds form inversion dimers and generate R22(10) rings. The structure also features C—H⋯F and C—H⋯π inter­actions along [100] and [010], respectively.

Related literature

For the synthesis and liquid crystal behaviour of the title compound, see: Mahadevan et al. (2013[Mahadevan, K. M., Harish Kumar, H. N., Masagalli, J. N. & Srinivasa, H. T. (2013). Mol. Cryst. Liq. Cryst. 570, 20-35.]). For the biological activity of coumarins and their derivatives, see: Borges et al. (2005[Borges, F., Roleira, F., Milhazes, N., Santana, L. & Uriarte, E. (2005). Curr. Med. Chem. 12, 887-916.]); Kontogiorgis & Hadjipavlou-Litina (2005[Kontogiorgis, C. A. & Hadjipavlou-Litina, D. J. (2005). J. Med. Chem. 48, 6400-6408.]) and for their industrial applications, see: Hejchman et al. (2011[Hejchman, E. B., Konc, J. T., Maciejewska, D. & Kruszewska, H. (2011). Synth. Commun. 41, 2392-2402.]). For the structure of 4-(oct­yloxy)phenyl 2-oxo-2H-chromene-3-carboxyl­ate, see: Palakshamurthy et al. (2013[Palakshamurthy, B. S., Sreenivasa, S., Srinivasa, H. T., Roopashree, K. R. & Devarajegowda, H. C. (2013). Acta Cryst. E69, o212.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C27H29F3O5

  • Mr = 490.50

  • Monoclinic, P 21 /c

  • a = 27.85 (3) Å

  • b = 9.281 (10) Å

  • c = 9.981 (11) Å

  • β = 94.849 (18)°

  • V = 2571 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 99 K

  • 0.52 × 0.42 × 0.40 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.950, Tmax = 0.961

  • 21163 measured reflections

  • 4448 independent reflections

  • 2547 reflections with I > 2σ(I)

  • Rint = 0.073

Refinement
  • R[F2 > 2σ(F2)] = 0.084

  • wR(F2) = 0.221

  • S = 1.07

  • 4448 reflections

  • 344 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C12–C17 rings respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10⋯O3i 0.95 2.56 3.396 (5) 146
C27—H27C⋯F1ii 0.98 2.52 3.432 (13) 154
C6—H6⋯Cg2i 0.95 3.09 3.899 144
C16—H16⋯Cg2iii 0.95 3.33 4.120 142
C3—H3⋯Cg1iv 0.95 3.43 4.325 163
Symmetry codes: (i) -x+1, -y+1, -z; (ii) [x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and 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: SHELXL97.

Supporting information


Comment top

The title compound is a liquid crystal (LC) exhibiting enantiotropic SmA phase transitions at 203.9(22.64) on heating and at 135.1(47.57) on cooling [The transition temperature in °C and the associated enthalpy values in kJ mol-1 (in italics)] (Mahadevan et al., 2013).

Organic compounds with a 2H-chromene ring system and their derivatives display a wide range of biological activities such as antiviral (Borges et al.., 2005) and anti-inflammatory (Kontogiorgis et al., 2005) activity. They also display photochemical and photophysical properties, acting as molecular fluorescent sensors, laser dyes and have many industrial applications (Hejchman et al., 2011). Keeping this in mind we report here the structure of the 4-(decyloxy)phenyl 7-(trifluoromethyl)-2-oxo-2H-chromene-3-carboxylate(I), and its comparision with 4-(octyloxy)phenyl 2-oxo-2H-chromene-3 –carboxylate(II) (Palakshamurthy et al., 2013).

The asymmetric unit of 4-(decyloxy)phenyl 7-(trifluoromethyl)-2-oxo-2H-chromene-3-carboxylate is shown in Fig.1. The three F atoms of the –CF3 group are disordered over two sets of sites with occupancy factors 0.71 (4):0.29 (4). The dihedral angles between the 2H-chromene ring and the benzene ring are 62.97 (2)o and 21.11 (1)° in the compounds I and II respectively. The crystal structure is characterized by intermolecular C10—H10···O3 hydrogen bonds that form inversion dimers and generate a R22(10) ring pattern (Bernstein et al., 1995). C27—H27···F1 hydrogen bonds then link the dimers into chains along a . The structure is further stabilized by C3—H3···Cg1, C6—H6···Cg2 and C16—H16···Cg2 interactions, Table 1.

Related literature top

For the synthesis and liquid crystal behaviour of the title compound, see: Mahadevan et al. (2013). For the biological activity of coumarins and their derivatives, see: Borges et al. (2005); Kontogiorgis & Hadjipavlou-Litina (2005) and for their industrial applications, see: Hejchman et al. (2011). For the structure of 4-(octyloxy)phenyl 2-oxo-2H-chromene-3-carboxylate, see: Palakshamurthy et al. (2013). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 7-(trifluoromethyl)-2-oxo-2H-chromene-3-carboxylic acid (0.100 g, 0.1 mmol), 4-(decyloxy) phenol (0.100 g, 0.1 mmol) dicyclohexylcarbodiimide (DCC) (0.100 g, 0.1 mmol) and catalytic quantity of DMAP (N,N-dimethyl amino pyridine) were stirred at room temperature for 48hrs in dry dichloromethane. Progress of the reaction was monitored by TLC (ethyl acetate: pet ether 2:8). After the completion of the reaction, the reaction mass was diluted with water and extracted into dichloromethane (25 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The crude product thus obtained was purified by column chromatography using ethyl acetate: petroleum ether (2:8) as eluent followed by recrystallization from ethanol. A single crystal suitable for X-ray diffraction was grown from ethanol.

Refinement top

The H atoms bound to carbon were positioned with idealized geometry using a riding model with d(C–H) = 0.93- 0.99 Å. All C–H atoms were refined with isotropic displacement parameters set to 1.2–1.5 Ueq(C). The F1, F2, and F3 fluorine atoms of the –CF3 group were disordered over two sites and refined with site occupancy factors 0.71 (4):0.29 (4). The crystals were not of high quality which accounts for the high uncertainties in the lengths of the unit cell axes and the relatively high residuals.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); 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, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level. Only the major component of the disordered CF3 group is shown.
[Figure 2] Fig. 2. Crystal packing of the title compound with hydrogen bonds drawn as dashed lines.
[Figure 3] Fig. 3. Packing of the title compound. C—H···π interactions are shown as dashed lines.
4-(Decyloxy)phenyl 2-oxo-7-trifluoromethyl-2H-chromene-3-carboxylate top
Crystal data top
C27H29F3O5prism
Mr = 490.50Dx = 1.267 Mg m3
Monoclinic, P21/cMelting point: 418 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 27.85 (3) ÅCell parameters from 2547 reflections
b = 9.281 (10) Åθ = 2.2–25°
c = 9.981 (11) ŵ = 0.10 mm1
β = 94.849 (18)°T = 99 K
V = 2571 (5) Å3Prism, colourless
Z = 40.52 × 0.42 × 0.40 mm
F(000) = 1032
Data collection top
Bruker APEXII
diffractometer
4448 independent reflections
Radiation source: fine-focus sealed tube2547 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
ϕ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
h = 3333
Tmin = 0.950, Tmax = 0.961k = 1111
21163 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.084Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0928P)2 + 0.7006P]
where P = (Fo2 + 2Fc2)/3
4448 reflections(Δ/σ)max = 0.004
344 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.17 e Å3
0 constraints
Crystal data top
C27H29F3O5V = 2571 (5) Å3
Mr = 490.50Z = 4
Monoclinic, P21/cMo Kα radiation
a = 27.85 (3) ŵ = 0.10 mm1
b = 9.281 (10) ÅT = 99 K
c = 9.981 (11) Å0.52 × 0.42 × 0.40 mm
β = 94.849 (18)°
Data collection top
Bruker APEXII
diffractometer
4448 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
2547 reflections with I > 2σ(I)
Tmin = 0.950, Tmax = 0.961Rint = 0.073
21163 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0840 restraints
wR(F2) = 0.221H-atom parameters constrained
S = 1.07Δρmax = 0.18 e Å3
4448 reflectionsΔρmin = 0.17 e Å3
344 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C251.0692 (2)0.6151 (7)0.3351 (7)0.150 (2)
H25A1.08670.65800.25430.179*
H25B1.07160.50930.32410.179*
C241.0184 (2)0.6518 (7)0.3292 (7)0.153 (2)
H24A1.01620.75790.33810.184*
H24B1.00120.61100.41130.184*
C20.31670 (15)0.6261 (4)0.2849 (4)0.0741 (11)
C10.26593 (19)0.6458 (7)0.3228 (6)0.0935 (13)
C271.1456 (2)0.6184 (9)0.4560 (9)0.208 (4)
H27A1.15560.65450.54170.312*
H27B1.15020.51380.45140.312*
H27C1.16520.66430.38160.312*
C261.0960 (3)0.6514 (10)0.4462 (8)0.213 (4)
H26A1.07830.60820.52650.256*
H26B1.09310.75710.45720.256*
F10.2363 (3)0.694 (2)0.2215 (10)0.137 (6)0.71 (4)
F20.2468 (5)0.5236 (12)0.361 (3)0.159 (9)0.71 (4)
F30.2620 (2)0.739 (2)0.4226 (19)0.145 (8)0.71 (4)
F1A0.2625 (6)0.621 (7)0.450 (2)0.154 (19)0.29 (4)
F2A0.2343 (8)0.556 (5)0.269 (5)0.147 (17)0.29 (4)
F3A0.2475 (14)0.766 (3)0.303 (7)0.18 (3)0.29 (4)
O10.43973 (9)0.6693 (2)0.4333 (2)0.0641 (7)
O40.57932 (9)0.6725 (3)0.2856 (2)0.0709 (7)
C100.46005 (13)0.5620 (3)0.1853 (3)0.0632 (10)
H100.46670.52240.10110.076*
C50.41071 (13)0.5803 (3)0.2142 (3)0.0589 (9)
O20.51778 (10)0.6830 (3)0.4977 (2)0.0840 (8)
C30.35544 (15)0.6606 (4)0.3744 (4)0.0694 (10)
H30.35030.70040.45970.083*
C80.48791 (14)0.6551 (3)0.4068 (3)0.0577 (9)
C40.40217 (13)0.6371 (3)0.3396 (3)0.0576 (9)
C90.49690 (13)0.5990 (3)0.2735 (3)0.0551 (8)
O30.55682 (9)0.4843 (3)0.1529 (3)0.0868 (9)
C60.37051 (14)0.5468 (4)0.1238 (4)0.0765 (11)
H60.37550.50860.03780.092*
C110.54679 (13)0.5768 (4)0.2315 (3)0.0611 (9)
C70.32407 (15)0.5687 (4)0.1581 (4)0.0843 (12)
H70.29730.54510.09650.101*
C120.62703 (14)0.6568 (4)0.2462 (4)0.0668 (10)
C170.64238 (15)0.7362 (4)0.1429 (4)0.0784 (11)
H170.62060.80010.09440.094*
C150.72109 (15)0.6315 (5)0.1777 (5)0.0847 (12)
C160.68960 (15)0.7248 (4)0.1077 (4)0.0831 (12)
H160.70000.78090.03600.100*
O50.76854 (11)0.6082 (4)0.1512 (4)0.1166 (11)
C130.65845 (18)0.5638 (5)0.3158 (4)0.0971 (14)
H130.64800.50830.38780.117*
C140.70536 (18)0.5511 (6)0.2811 (5)0.1108 (16)
H140.72690.48630.32920.133*
C190.83692 (17)0.6115 (6)0.0247 (5)0.1171 (17)
H19A0.85730.63860.10700.141*
H19B0.83500.50500.02250.141*
C180.78703 (16)0.6698 (5)0.0363 (5)0.1025 (15)
H18A0.78820.77600.04500.123*
H18B0.76590.64510.04530.123*
C200.86150 (18)0.6598 (6)0.0933 (6)0.1232 (18)
H20A0.86090.76650.09520.148*
H20B0.84250.62570.17540.148*
C230.99056 (18)0.6129 (7)0.2183 (6)0.134 (2)
H23A1.00810.65180.13570.161*
H23B0.99200.50660.21070.161*
C210.91271 (18)0.6116 (7)0.1003 (6)0.1294 (19)
H21A0.93130.64570.01740.155*
H21B0.91280.50500.09690.155*
C220.9393 (2)0.6543 (7)0.2135 (6)0.137 (2)
H22A0.93770.76070.21970.165*
H22B0.92160.61600.29600.165*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C250.088 (4)0.175 (6)0.191 (6)0.014 (4)0.044 (4)0.019 (5)
C240.103 (4)0.190 (6)0.172 (6)0.028 (4)0.051 (4)0.016 (5)
C20.076 (3)0.068 (2)0.081 (3)0.002 (2)0.025 (2)0.011 (2)
C10.090 (4)0.099 (4)0.095 (4)0.004 (3)0.026 (3)0.011 (3)
C270.108 (5)0.243 (9)0.282 (10)0.012 (5)0.066 (6)0.009 (8)
C260.137 (7)0.279 (10)0.235 (9)0.037 (6)0.088 (6)0.023 (8)
F10.097 (4)0.197 (15)0.118 (6)0.045 (6)0.021 (4)0.027 (6)
F20.103 (8)0.120 (6)0.26 (2)0.014 (5)0.083 (12)0.075 (10)
F30.094 (4)0.190 (15)0.158 (11)0.008 (6)0.043 (5)0.069 (11)
F1A0.106 (11)0.25 (5)0.117 (13)0.009 (18)0.061 (9)0.032 (18)
F2A0.083 (10)0.15 (3)0.21 (3)0.011 (12)0.038 (14)0.03 (2)
F3A0.18 (2)0.12 (2)0.27 (6)0.079 (18)0.10 (4)0.07 (3)
O10.0811 (17)0.0674 (15)0.0456 (13)0.0026 (12)0.0160 (12)0.0070 (11)
O40.0756 (17)0.0752 (16)0.0639 (15)0.0077 (13)0.0181 (12)0.0240 (13)
C100.083 (3)0.067 (2)0.0423 (19)0.0066 (18)0.0218 (19)0.0059 (16)
C50.072 (2)0.059 (2)0.0467 (19)0.0125 (17)0.0157 (18)0.0017 (15)
O20.089 (2)0.115 (2)0.0480 (14)0.0021 (16)0.0037 (14)0.0223 (14)
C30.086 (3)0.064 (2)0.061 (2)0.004 (2)0.025 (2)0.0030 (17)
C80.078 (3)0.0537 (19)0.0421 (19)0.0018 (17)0.0112 (18)0.0019 (15)
C40.076 (2)0.0484 (18)0.050 (2)0.0019 (16)0.0143 (18)0.0045 (15)
C90.077 (2)0.0517 (18)0.0377 (18)0.0050 (16)0.0124 (17)0.0009 (14)
O30.0876 (19)0.0923 (19)0.0828 (18)0.0046 (15)0.0212 (15)0.0405 (15)
C60.081 (3)0.091 (3)0.060 (2)0.017 (2)0.019 (2)0.006 (2)
C110.080 (3)0.062 (2)0.0414 (18)0.0022 (19)0.0086 (17)0.0041 (16)
C70.078 (3)0.102 (3)0.074 (3)0.013 (2)0.011 (2)0.001 (2)
C120.071 (2)0.070 (2)0.059 (2)0.002 (2)0.0062 (19)0.0184 (19)
C170.078 (3)0.072 (2)0.086 (3)0.002 (2)0.011 (2)0.004 (2)
C150.069 (3)0.096 (3)0.090 (3)0.002 (2)0.012 (2)0.013 (3)
C160.070 (3)0.081 (3)0.100 (3)0.005 (2)0.017 (2)0.005 (2)
O50.076 (2)0.146 (3)0.129 (3)0.0163 (19)0.013 (2)0.006 (2)
C130.105 (4)0.118 (4)0.070 (3)0.015 (3)0.019 (2)0.016 (3)
C140.094 (4)0.144 (4)0.096 (3)0.037 (3)0.011 (3)0.018 (3)
C190.067 (3)0.150 (5)0.135 (4)0.004 (3)0.016 (3)0.000 (4)
C180.077 (3)0.105 (3)0.128 (4)0.007 (3)0.026 (3)0.015 (3)
C200.085 (3)0.138 (4)0.151 (5)0.009 (3)0.035 (3)0.007 (4)
C230.077 (3)0.161 (5)0.166 (5)0.012 (3)0.028 (3)0.015 (4)
C210.076 (3)0.160 (5)0.154 (5)0.011 (3)0.022 (3)0.013 (4)
C220.091 (4)0.171 (5)0.154 (5)0.020 (4)0.036 (4)0.003 (4)
Geometric parameters (Å, º) top
C25—C261.429 (8)C9—C111.499 (5)
C25—C241.460 (8)O3—C111.212 (4)
C25—H25A0.9900C6—C71.381 (5)
C25—H25B0.9900C6—H60.9500
C24—C231.451 (7)C7—H70.9500
C24—H24A0.9900C12—C171.365 (5)
C24—H24B0.9900C12—C131.375 (5)
C2—C31.379 (5)C17—C161.394 (5)
C2—C71.404 (5)C17—H170.9500
C2—C11.506 (6)C15—C141.375 (6)
C1—F3A1.234 (17)C15—C161.380 (6)
C1—F1A1.300 (18)C15—O51.387 (5)
C1—F2A1.30 (2)C16—H160.9500
C1—F21.323 (11)O5—C181.417 (5)
C1—F11.329 (9)C13—C141.385 (6)
C1—F31.332 (9)C13—H130.9500
C27—C261.426 (9)C14—H140.9500
C27—H27A0.9800C19—C201.481 (7)
C27—H27B0.9800C19—C181.505 (6)
C27—H27C0.9800C19—H19A0.9900
C26—H26A0.9900C19—H19B0.9900
C26—H26B0.9900C18—H18A0.9900
O1—C41.376 (4)C18—H18B0.9900
O1—C81.396 (4)C20—C211.502 (7)
O4—C111.349 (4)C20—H20A0.9900
O4—C121.425 (4)C20—H20B0.9900
C10—C91.339 (5)C23—C221.482 (7)
C10—C51.438 (5)C23—H23A0.9900
C10—H100.9500C23—H23B0.9900
C5—C41.397 (4)C21—C221.458 (7)
C5—C61.412 (5)C21—H21A0.9900
O2—C81.206 (4)C21—H21B0.9900
C3—C41.392 (5)C22—H22A0.9900
C3—H30.9500C22—H22B0.9900
C8—C91.469 (4)
C26—C25—C24123.3 (7)C10—C9—C11117.2 (3)
C26—C25—H25A106.5C8—C9—C11122.3 (3)
C24—C25—H25A106.5C7—C6—C5121.2 (4)
C26—C25—H25B106.5C7—C6—H6119.4
C24—C25—H25B106.5C5—C6—H6119.4
H25A—C25—H25B106.5O3—C11—O4122.8 (3)
C23—C24—C25123.7 (6)O3—C11—C9123.3 (3)
C23—C24—H24A106.4O4—C11—C9113.9 (3)
C25—C24—H24A106.4C6—C7—C2119.4 (4)
C23—C24—H24B106.4C6—C7—H7120.3
C25—C24—H24B106.4C2—C7—H7120.3
H24A—C24—H24B106.5C17—C12—C13119.6 (4)
C3—C2—C7120.4 (4)C17—C12—O4120.8 (3)
C3—C2—C1120.6 (4)C13—C12—O4119.6 (4)
C7—C2—C1119.0 (4)C12—C17—C16120.8 (4)
F3A—C1—F1A104.7 (15)C12—C17—H17119.6
F3A—C1—F2A104.9 (19)C16—C17—H17119.6
F1A—C1—F2A100.8 (14)C14—C15—C16119.4 (4)
F3A—C1—F2130.3 (12)C14—C15—O5115.4 (4)
F1A—C1—F260.1 (18)C16—C15—O5125.2 (4)
F2A—C1—F244.9 (18)C15—C16—C17119.5 (4)
F3A—C1—F150 (3)C15—C16—H16120.2
F1A—C1—F1135.3 (10)C17—C16—H16120.2
F2A—C1—F163 (2)C15—O5—C18120.6 (4)
F2—C1—F1105.6 (10)C12—C13—C14120.1 (4)
F3A—C1—F358 (3)C12—C13—H13120.0
F1A—C1—F351 (2)C14—C13—H13120.0
F2A—C1—F3129.4 (10)C15—C14—C13120.6 (4)
F2—C1—F3106.4 (8)C15—C14—H14119.7
F1—C1—F3105.3 (7)C13—C14—H14119.7
F3A—C1—C2117.1 (10)C20—C19—C18116.3 (5)
F1A—C1—C2111.8 (10)C20—C19—H19A108.2
F2A—C1—C2115.8 (9)C18—C19—H19A108.2
F2—C1—C2112.2 (6)C20—C19—H19B108.2
F1—C1—C2112.7 (5)C18—C19—H19B108.2
F3—C1—C2113.9 (6)H19A—C19—H19B107.4
C26—C27—H27A109.5O5—C18—C19108.5 (4)
C26—C27—H27B109.5O5—C18—H18A110.0
H27A—C27—H27B109.5C19—C18—H18A110.0
C26—C27—H27C109.5O5—C18—H18B110.0
H27A—C27—H27C109.5C19—C18—H18B110.0
H27B—C27—H27C109.5H18A—C18—H18B108.4
C27—C26—C25125.2 (8)C19—C20—C21116.8 (5)
C27—C26—H26A106.0C19—C20—H20A108.1
C25—C26—H26A106.0C21—C20—H20A108.1
C27—C26—H26B106.0C19—C20—H20B108.1
C25—C26—H26B106.0C21—C20—H20B108.1
H26A—C26—H26B106.3H20A—C20—H20B107.3
C4—O1—C8122.6 (3)C24—C23—C22122.6 (5)
C11—O4—C12115.6 (3)C24—C23—H23A106.7
C9—C10—C5122.1 (3)C22—C23—H23A106.7
C9—C10—H10119.0C24—C23—H23B106.7
C5—C10—H10119.0C22—C23—H23B106.7
C4—C5—C6118.0 (3)H23A—C23—H23B106.6
C4—C5—C10117.5 (3)C22—C21—C20120.2 (5)
C6—C5—C10124.5 (3)C22—C21—H21A107.3
C2—C3—C4119.9 (3)C20—C21—H21A107.3
C2—C3—H3120.0C22—C21—H21B107.3
C4—C3—H3120.0C20—C21—H21B107.3
O2—C8—O1116.8 (3)H21A—C21—H21B106.9
O2—C8—C9126.7 (3)C21—C22—C23120.6 (5)
O1—C8—C9116.4 (3)C21—C22—H22A107.2
O1—C4—C3118.0 (3)C23—C22—H22A107.2
O1—C4—C5120.9 (3)C21—C22—H22B107.2
C3—C4—C5121.1 (4)C23—C22—H22B107.2
C10—C9—C8120.4 (3)H22A—C22—H22B106.8
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2–C7 and C12–C17 rings respectively.
D—H···AD—HH···AD···AD—H···A
C10—H10···O3i0.952.563.396 (5)146
C27—H27C···F1ii0.982.523.432 (13)154
C6—H6···Cg2i0.953.093.899144
C16—H16···Cg2iii0.953.334.120142
C3—H3···Cg1iv0.953.434.325163
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+3/2, z1/2; (iii) x, y+3/2, z1/2; (iv) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC27H29F3O5
Mr490.50
Crystal system, space groupMonoclinic, P21/c
Temperature (K)99
a, b, c (Å)27.85 (3), 9.281 (10), 9.981 (11)
β (°) 94.849 (18)
V3)2571 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.52 × 0.42 × 0.40
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.950, 0.961
No. of measured, independent and
observed [I > 2σ(I)] reflections
21163, 4448, 2547
Rint0.073
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.084, 0.221, 1.07
No. of reflections4448
No. of parameters344
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.17

Computer programs: APEX2 (Bruker, 2009), APEX2 and SAINT-Plus (Bruker, 2009), SAINT-Plus and XPREP (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2–C7 and C12–C17 rings respectively.
D—H···AD—HH···AD···AD—H···A
C10—H10···O3i0.952.563.396 (5)146.2
C27—H27C···F1ii0.982.523.432 (13)154.4
C6—H6···Cg2i0.953.0893.899144.29
C16—H16···Cg2iii0.953.3284.120142.31
C3—H3···Cg1iv0.953.4254.325162.61
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+3/2, z1/2; (iii) x, y+3/2, z1/2; (iv) x, y+3/2, z+1/2.
 

Acknowledgements

The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, and G. B. Sadananda, Department of Studies and Research in Physics, U·C.S. Tumkur University, Tumkur.

References

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Volume 69| Part 4| April 2013| Pages o621-o622
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