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

Palakshamurthy, B.S.; Devarajegowda, H.C.; Srinivasa, H.T.; Sreenivasa, S.; Vijithkumar

doi:10.1107/S1600536813008222

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

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

doi:10.1107/S1600536813008222

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

B. S. Palakshamurthy,^a ^* H. C. Devarajegowda,^a H. T. Srinivasa,^b S. Sreenivasa ^c and Vijithkumar ^d

^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 ). 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

Crystal data

C₂₇H₂₉F₃O₅
M_r = 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 ) T_min = 0.950, T_max = 0.961
21163 measured reflections
4448 independent reflections
2547 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.084
wR(F²) = 0.221
S = 1.07
4448 reflections
344 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −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	D⋯A	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⋯Cg1^iv	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 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813008222/sj5309sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813008222/sj5309Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813008222/sj5309Isup3.cml

checkCIF report

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.

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

	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.
	Fig. 2. Crystal packing of the title compound with hydrogen bonds drawn as dashed lines.
	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

C₂₇H₂₉F₃O₅	prism
M_r = 490.50	D_x = 1.267 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 418 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 27.85 (3) Å	Cell parameters from 2547 reflections
b = 9.281 (10) Å	θ = 2.2–25°
c = 9.981 (11) Å	µ = 0.10 mm⁻¹
β = 94.849 (18)°	T = 99 K
V = 2571 (5) Å³	Prism, colourless
Z = 4	0.52 × 0.42 × 0.40 mm
F(000) = 1032

Data collection top

Bruker APEXII diffractometer	4448 independent reflections
Radiation source: fine-focus sealed tube	2547 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −33→33
T_min = 0.950, T_max = 0.961	k = −11→11
21163 measured reflections	l = −11→11

Refinement top

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.221	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0928P)² + 0.7006P] where P = (F_o² + 2F_c²)/3
4448 reflections	(Δ/σ)_max = 0.004
344 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³
0 constraints

Crystal data top

C₂₇H₂₉F₃O₅	V = 2571 (5) Å³
M_r = 490.50	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 27.85 (3) Å	µ = 0.10 mm⁻¹
b = 9.281 (10) Å	T = 99 K
c = 9.981 (11) Å	0.52 × 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)
T_min = 0.950, T_max = 0.961	R_int = 0.073
21163 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	0 restraints
wR(F²) = 0.221	H-atom parameters constrained
S = 1.07	Δρ_max = 0.18 e Å⁻³
4448 reflections	Δρ_min = −0.17 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C25	1.0692 (2)	0.6151 (7)	−0.3351 (7)	0.150 (2)
H25A	1.0867	0.6580	−0.2543	0.179*
H25B	1.0716	0.5093	−0.3241	0.179*
C24	1.0184 (2)	0.6518 (7)	−0.3292 (7)	0.153 (2)
H24A	1.0162	0.7579	−0.3381	0.184*
H24B	1.0012	0.6110	−0.4113	0.184*
C2	0.31670 (15)	0.6261 (4)	0.2849 (4)	0.0741 (11)
C1	0.26593 (19)	0.6458 (7)	0.3228 (6)	0.0935 (13)
C27	1.1456 (2)	0.6184 (9)	−0.4560 (9)	0.208 (4)
H27A	1.1556	0.6545	−0.5417	0.312*
H27B	1.1502	0.5138	−0.4514	0.312*
H27C	1.1652	0.6643	−0.3816	0.312*
C26	1.0960 (3)	0.6514 (10)	−0.4462 (8)	0.213 (4)
H26A	1.0783	0.6082	−0.5265	0.256*
H26B	1.0931	0.7571	−0.4572	0.256*
F1	0.2363 (3)	0.694 (2)	0.2215 (10)	0.137 (6)	0.71 (4)
F2	0.2468 (5)	0.5236 (12)	0.361 (3)	0.159 (9)	0.71 (4)
F3	0.2620 (2)	0.739 (2)	0.4226 (19)	0.145 (8)	0.71 (4)
F1A	0.2625 (6)	0.621 (7)	0.450 (2)	0.154 (19)	0.29 (4)
F2A	0.2343 (8)	0.556 (5)	0.269 (5)	0.147 (17)	0.29 (4)
F3A	0.2475 (14)	0.766 (3)	0.303 (7)	0.18 (3)	0.29 (4)
O1	0.43973 (9)	0.6693 (2)	0.4333 (2)	0.0641 (7)
O4	0.57932 (9)	0.6725 (3)	0.2856 (2)	0.0709 (7)
C10	0.46005 (13)	0.5620 (3)	0.1853 (3)	0.0632 (10)
H10	0.4667	0.5224	0.1011	0.076*
C5	0.41071 (13)	0.5803 (3)	0.2142 (3)	0.0589 (9)
O2	0.51778 (10)	0.6830 (3)	0.4977 (2)	0.0840 (8)
C3	0.35544 (15)	0.6606 (4)	0.3744 (4)	0.0694 (10)
H3	0.3503	0.7004	0.4597	0.083*
C8	0.48791 (14)	0.6551 (3)	0.4068 (3)	0.0577 (9)
C4	0.40217 (13)	0.6371 (3)	0.3396 (3)	0.0576 (9)
C9	0.49690 (13)	0.5990 (3)	0.2735 (3)	0.0551 (8)
O3	0.55682 (9)	0.4843 (3)	0.1529 (3)	0.0868 (9)
C6	0.37051 (14)	0.5468 (4)	0.1238 (4)	0.0765 (11)
H6	0.3755	0.5086	0.0378	0.092*
C11	0.54679 (13)	0.5768 (4)	0.2315 (3)	0.0611 (9)
C7	0.32407 (15)	0.5687 (4)	0.1581 (4)	0.0843 (12)
H7	0.2973	0.5451	0.0965	0.101*
C12	0.62703 (14)	0.6568 (4)	0.2462 (4)	0.0668 (10)
C17	0.64238 (15)	0.7362 (4)	0.1429 (4)	0.0784 (11)
H17	0.6206	0.8001	0.0944	0.094*
C15	0.72109 (15)	0.6315 (5)	0.1777 (5)	0.0847 (12)
C16	0.68960 (15)	0.7248 (4)	0.1077 (4)	0.0831 (12)
H16	0.7000	0.7809	0.0360	0.100*
O5	0.76854 (11)	0.6082 (4)	0.1512 (4)	0.1166 (11)
C13	0.65845 (18)	0.5638 (5)	0.3158 (4)	0.0971 (14)
H13	0.6480	0.5083	0.3878	0.117*
C14	0.70536 (18)	0.5511 (6)	0.2811 (5)	0.1108 (16)
H14	0.7269	0.4863	0.3292	0.133*
C19	0.83692 (17)	0.6115 (6)	0.0247 (5)	0.1171 (17)
H19A	0.8573	0.6386	0.1070	0.141*
H19B	0.8350	0.5050	0.0225	0.141*
C18	0.78703 (16)	0.6698 (5)	0.0363 (5)	0.1025 (15)
H18A	0.7882	0.7760	0.0450	0.123*
H18B	0.7659	0.6451	−0.0453	0.123*
C20	0.86150 (18)	0.6598 (6)	−0.0933 (6)	0.1232 (18)
H20A	0.8609	0.7665	−0.0952	0.148*
H20B	0.8425	0.6257	−0.1754	0.148*
C23	0.99056 (18)	0.6129 (7)	−0.2183 (6)	0.134 (2)
H23A	1.0081	0.6518	−0.1357	0.161*
H23B	0.9920	0.5066	−0.2107	0.161*
C21	0.91271 (18)	0.6116 (7)	−0.1003 (6)	0.1294 (19)
H21A	0.9313	0.6457	−0.0174	0.155*
H21B	0.9128	0.5050	−0.0969	0.155*
C22	0.9393 (2)	0.6543 (7)	−0.2135 (6)	0.137 (2)
H22A	0.9377	0.7607	−0.2197	0.165*
H22B	0.9216	0.6160	−0.2960	0.165*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C25	0.088 (4)	0.175 (6)	0.191 (6)	0.014 (4)	0.044 (4)	0.019 (5)
C24	0.103 (4)	0.190 (6)	0.172 (6)	0.028 (4)	0.051 (4)	0.016 (5)
C2	0.076 (3)	0.068 (2)	0.081 (3)	0.002 (2)	0.025 (2)	0.011 (2)
C1	0.090 (4)	0.099 (4)	0.095 (4)	0.004 (3)	0.026 (3)	0.011 (3)
C27	0.108 (5)	0.243 (9)	0.282 (10)	0.012 (5)	0.066 (6)	0.009 (8)
C26	0.137 (7)	0.279 (10)	0.235 (9)	0.037 (6)	0.088 (6)	0.023 (8)
F1	0.097 (4)	0.197 (15)	0.118 (6)	0.045 (6)	0.021 (4)	0.027 (6)
F2	0.103 (8)	0.120 (6)	0.26 (2)	0.014 (5)	0.083 (12)	0.075 (10)
F3	0.094 (4)	0.190 (15)	0.158 (11)	0.008 (6)	0.043 (5)	−0.069 (11)
F1A	0.106 (11)	0.25 (5)	0.117 (13)	0.009 (18)	0.061 (9)	0.032 (18)
F2A	0.083 (10)	0.15 (3)	0.21 (3)	−0.011 (12)	0.038 (14)	−0.03 (2)
F3A	0.18 (2)	0.12 (2)	0.27 (6)	0.079 (18)	0.10 (4)	0.07 (3)
O1	0.0811 (17)	0.0674 (15)	0.0456 (13)	0.0026 (12)	0.0160 (12)	−0.0070 (11)
O4	0.0756 (17)	0.0752 (16)	0.0639 (15)	−0.0077 (13)	0.0181 (12)	−0.0240 (13)
C10	0.083 (3)	0.067 (2)	0.0423 (19)	−0.0066 (18)	0.0218 (19)	−0.0059 (16)
C5	0.072 (2)	0.059 (2)	0.0467 (19)	−0.0125 (17)	0.0157 (18)	−0.0017 (15)
O2	0.089 (2)	0.115 (2)	0.0480 (14)	0.0021 (16)	0.0037 (14)	−0.0223 (14)
C3	0.086 (3)	0.064 (2)	0.061 (2)	0.004 (2)	0.025 (2)	0.0030 (17)
C8	0.078 (3)	0.0537 (19)	0.0421 (19)	0.0018 (17)	0.0112 (18)	−0.0019 (15)
C4	0.076 (2)	0.0484 (18)	0.050 (2)	−0.0019 (16)	0.0143 (18)	0.0045 (15)
C9	0.077 (2)	0.0517 (18)	0.0377 (18)	−0.0050 (16)	0.0124 (17)	−0.0009 (14)
O3	0.0876 (19)	0.0923 (19)	0.0828 (18)	−0.0046 (15)	0.0212 (15)	−0.0405 (15)
C6	0.081 (3)	0.091 (3)	0.060 (2)	−0.017 (2)	0.019 (2)	−0.006 (2)
C11	0.080 (3)	0.062 (2)	0.0414 (18)	−0.0022 (19)	0.0086 (17)	−0.0041 (16)
C7	0.078 (3)	0.102 (3)	0.074 (3)	−0.013 (2)	0.011 (2)	−0.001 (2)
C12	0.071 (2)	0.070 (2)	0.059 (2)	0.002 (2)	0.0062 (19)	−0.0184 (19)
C17	0.078 (3)	0.072 (2)	0.086 (3)	0.002 (2)	0.011 (2)	0.004 (2)
C15	0.069 (3)	0.096 (3)	0.090 (3)	0.002 (2)	0.012 (2)	−0.013 (3)
C16	0.070 (3)	0.081 (3)	0.100 (3)	−0.005 (2)	0.017 (2)	0.005 (2)
O5	0.076 (2)	0.146 (3)	0.129 (3)	0.0163 (19)	0.013 (2)	0.006 (2)
C13	0.105 (4)	0.118 (4)	0.070 (3)	0.015 (3)	0.019 (2)	0.016 (3)
C14	0.094 (4)	0.144 (4)	0.096 (3)	0.037 (3)	0.011 (3)	0.018 (3)
C19	0.067 (3)	0.150 (5)	0.135 (4)	0.004 (3)	0.016 (3)	0.000 (4)
C18	0.077 (3)	0.105 (3)	0.128 (4)	−0.007 (3)	0.026 (3)	−0.015 (3)
C20	0.085 (3)	0.138 (4)	0.151 (5)	0.009 (3)	0.035 (3)	−0.007 (4)
C23	0.077 (3)	0.161 (5)	0.166 (5)	0.012 (3)	0.028 (3)	0.015 (4)
C21	0.076 (3)	0.160 (5)	0.154 (5)	0.011 (3)	0.022 (3)	0.013 (4)
C22	0.091 (4)	0.171 (5)	0.154 (5)	0.020 (4)	0.036 (4)	0.003 (4)

Geometric parameters (Å, º) top

C25—C26	1.429 (8)	C9—C11	1.499 (5)
C25—C24	1.460 (8)	O3—C11	1.212 (4)
C25—H25A	0.9900	C6—C7	1.381 (5)
C25—H25B	0.9900	C6—H6	0.9500
C24—C23	1.451 (7)	C7—H7	0.9500
C24—H24A	0.9900	C12—C17	1.365 (5)
C24—H24B	0.9900	C12—C13	1.375 (5)
C2—C3	1.379 (5)	C17—C16	1.394 (5)
C2—C7	1.404 (5)	C17—H17	0.9500
C2—C1	1.506 (6)	C15—C14	1.375 (6)
C1—F3A	1.234 (17)	C15—C16	1.380 (6)
C1—F1A	1.300 (18)	C15—O5	1.387 (5)
C1—F2A	1.30 (2)	C16—H16	0.9500
C1—F2	1.323 (11)	O5—C18	1.417 (5)
C1—F1	1.329 (9)	C13—C14	1.385 (6)
C1—F3	1.332 (9)	C13—H13	0.9500
C27—C26	1.426 (9)	C14—H14	0.9500
C27—H27A	0.9800	C19—C20	1.481 (7)
C27—H27B	0.9800	C19—C18	1.505 (6)
C27—H27C	0.9800	C19—H19A	0.9900
C26—H26A	0.9900	C19—H19B	0.9900
C26—H26B	0.9900	C18—H18A	0.9900
O1—C4	1.376 (4)	C18—H18B	0.9900
O1—C8	1.396 (4)	C20—C21	1.502 (7)
O4—C11	1.349 (4)	C20—H20A	0.9900
O4—C12	1.425 (4)	C20—H20B	0.9900
C10—C9	1.339 (5)	C23—C22	1.482 (7)
C10—C5	1.438 (5)	C23—H23A	0.9900
C10—H10	0.9500	C23—H23B	0.9900
C5—C4	1.397 (4)	C21—C22	1.458 (7)
C5—C6	1.412 (5)	C21—H21A	0.9900
O2—C8	1.206 (4)	C21—H21B	0.9900
C3—C4	1.392 (5)	C22—H22A	0.9900
C3—H3	0.9500	C22—H22B	0.9900
C8—C9	1.469 (4)

C26—C25—C24	123.3 (7)	C10—C9—C11	117.2 (3)
C26—C25—H25A	106.5	C8—C9—C11	122.3 (3)
C24—C25—H25A	106.5	C7—C6—C5	121.2 (4)
C26—C25—H25B	106.5	C7—C6—H6	119.4
C24—C25—H25B	106.5	C5—C6—H6	119.4
H25A—C25—H25B	106.5	O3—C11—O4	122.8 (3)
C23—C24—C25	123.7 (6)	O3—C11—C9	123.3 (3)
C23—C24—H24A	106.4	O4—C11—C9	113.9 (3)
C25—C24—H24A	106.4	C6—C7—C2	119.4 (4)
C23—C24—H24B	106.4	C6—C7—H7	120.3
C25—C24—H24B	106.4	C2—C7—H7	120.3
H24A—C24—H24B	106.5	C17—C12—C13	119.6 (4)
C3—C2—C7	120.4 (4)	C17—C12—O4	120.8 (3)
C3—C2—C1	120.6 (4)	C13—C12—O4	119.6 (4)
C7—C2—C1	119.0 (4)	C12—C17—C16	120.8 (4)
F3A—C1—F1A	104.7 (15)	C12—C17—H17	119.6
F3A—C1—F2A	104.9 (19)	C16—C17—H17	119.6
F1A—C1—F2A	100.8 (14)	C14—C15—C16	119.4 (4)
F3A—C1—F2	130.3 (12)	C14—C15—O5	115.4 (4)
F1A—C1—F2	60.1 (18)	C16—C15—O5	125.2 (4)
F2A—C1—F2	44.9 (18)	C15—C16—C17	119.5 (4)
F3A—C1—F1	50 (3)	C15—C16—H16	120.2
F1A—C1—F1	135.3 (10)	C17—C16—H16	120.2
F2A—C1—F1	63 (2)	C15—O5—C18	120.6 (4)
F2—C1—F1	105.6 (10)	C12—C13—C14	120.1 (4)
F3A—C1—F3	58 (3)	C12—C13—H13	120.0
F1A—C1—F3	51 (2)	C14—C13—H13	120.0
F2A—C1—F3	129.4 (10)	C15—C14—C13	120.6 (4)
F2—C1—F3	106.4 (8)	C15—C14—H14	119.7
F1—C1—F3	105.3 (7)	C13—C14—H14	119.7
F3A—C1—C2	117.1 (10)	C20—C19—C18	116.3 (5)
F1A—C1—C2	111.8 (10)	C20—C19—H19A	108.2
F2A—C1—C2	115.8 (9)	C18—C19—H19A	108.2
F2—C1—C2	112.2 (6)	C20—C19—H19B	108.2
F1—C1—C2	112.7 (5)	C18—C19—H19B	108.2
F3—C1—C2	113.9 (6)	H19A—C19—H19B	107.4
C26—C27—H27A	109.5	O5—C18—C19	108.5 (4)
C26—C27—H27B	109.5	O5—C18—H18A	110.0
H27A—C27—H27B	109.5	C19—C18—H18A	110.0
C26—C27—H27C	109.5	O5—C18—H18B	110.0
H27A—C27—H27C	109.5	C19—C18—H18B	110.0
H27B—C27—H27C	109.5	H18A—C18—H18B	108.4
C27—C26—C25	125.2 (8)	C19—C20—C21	116.8 (5)
C27—C26—H26A	106.0	C19—C20—H20A	108.1
C25—C26—H26A	106.0	C21—C20—H20A	108.1
C27—C26—H26B	106.0	C19—C20—H20B	108.1
C25—C26—H26B	106.0	C21—C20—H20B	108.1
H26A—C26—H26B	106.3	H20A—C20—H20B	107.3
C4—O1—C8	122.6 (3)	C24—C23—C22	122.6 (5)
C11—O4—C12	115.6 (3)	C24—C23—H23A	106.7
C9—C10—C5	122.1 (3)	C22—C23—H23A	106.7
C9—C10—H10	119.0	C24—C23—H23B	106.7
C5—C10—H10	119.0	C22—C23—H23B	106.7
C4—C5—C6	118.0 (3)	H23A—C23—H23B	106.6
C4—C5—C10	117.5 (3)	C22—C21—C20	120.2 (5)
C6—C5—C10	124.5 (3)	C22—C21—H21A	107.3
C2—C3—C4	119.9 (3)	C20—C21—H21A	107.3
C2—C3—H3	120.0	C22—C21—H21B	107.3
C4—C3—H3	120.0	C20—C21—H21B	107.3
O2—C8—O1	116.8 (3)	H21A—C21—H21B	106.9
O2—C8—C9	126.7 (3)	C21—C22—C23	120.6 (5)
O1—C8—C9	116.4 (3)	C21—C22—H22A	107.2
O1—C4—C3	118.0 (3)	C23—C22—H22A	107.2
O1—C4—C5	120.9 (3)	C21—C22—H22B	107.2
C3—C4—C5	121.1 (4)	C23—C22—H22B	107.2
C10—C9—C8	120.4 (3)	H22A—C22—H22B	106.8

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	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···Cg1^iv	0.95	3.43	4.325	163

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, −y+3/2, z−1/2; (iii) x, −y+3/2, z−1/2; (iv) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₉F₃O₅
M_r	490.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	99
a, b, c (Å)	27.85 (3), 9.281 (10), 9.981 (11)
β (°)	94.849 (18)
V (Å³)	2571 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.52 × 0.42 × 0.40

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.950, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	21163, 4448, 2547
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.221, 1.07
No. of reflections	4448
No. of parameters	344
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C10—H10···O3ⁱ	0.95	2.56	3.396 (5)	146.2
C27—H27C···F1ⁱⁱ	0.98	2.52	3.432 (13)	154.4
C6—H6···Cg2ⁱ	0.95	3.089	3.899	144.29
C16—H16···Cg2ⁱⁱⁱ	0.95	3.328	4.120	142.31
C3—H3···Cg1^iv	0.95	3.425	4.325	162.61

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, −y+3/2, z−1/2; (iii) x, −y+3/2, z−1/2; (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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