




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813008222/sj5309sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536813008222/sj5309Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813008222/sj5309Isup3.cml |
CCDC reference: 935711
Key indicators
- Single-crystal X-ray study
- T = 99 K
- Mean
(C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.084
- wR factor = 0.221
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level A DIFF019_ALERT_1_A _diffrn_standards_number is missing Number of standards used in measurement. DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards. DIFF022_ALERT_1_A _diffrn_standards_decay_% is missing Percentage decrease in standards intensity.
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C26
Alert level C PLAT148_ALERT_3_C su on the a - Axis is (Too) Large ........ 0.030 Ang. PLAT148_ALERT_3_C su on the b - Axis is (Too) Large ........ 0.0100 Ang. PLAT148_ALERT_3_C su on the c - Axis is (Too) Large ........ 0.011 Ang. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.9 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Uiso(max)/Uiso(min) .. 4.1 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0067 Ang PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C25 - C26 ... 1.43 Ang. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C26 - C27 ... 1.43 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C16 .. CG2 .. 4.12 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C3 .. CG1 .. 4.32 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 50.603 PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 7.990 PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 3.278 PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.055 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 53
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 9 Perc. PLAT343_ALERT_2_G Check sp3 Angle Range in Main Residue for .. C26 PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 21 F2A -C1 -F2 1.555 1.555 1.555 44.90 Deg. PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... !
3 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 21 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 12 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
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.
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.
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).
C27H29F3O5 | prism |
Mr = 490.50 | Dx = 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 |
Bruker APEXII diffractometer | 4448 independent reflections |
Radiation source: fine-focus sealed tube | 2547 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | h = −33→33 |
Tmin = 0.950, Tmax = 0.961 | k = −11→11 |
21163 measured reflections | l = −11→11 |
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(Fo2) + (0.0928P)2 + 0.7006P] where P = (Fo2 + 2Fc2)/3 |
4448 reflections | (Δ/σ)max = 0.004 |
344 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
0 constraints |
C27H29F3O5 | V = 2571 (5) Å3 |
Mr = 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)° |
Bruker APEXII diffractometer | 4448 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | 2547 reflections with I > 2σ(I) |
Tmin = 0.950, Tmax = 0.961 | Rint = 0.073 |
21163 measured reflections |
R[F2 > 2σ(F2)] = 0.084 | 0 restraints |
wR(F2) = 0.221 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.18 e Å−3 |
4448 reflections | Δρmin = −0.17 e Å−3 |
344 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) | |
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* |
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) |
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 |
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···Cg1iv | 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 |
Mr | 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) |
Tmin, Tmax | 0.950, 0.961 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21163, 4448, 2547 |
Rint | 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 |
Δρmax, Δρmin (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).
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···Cg1iv | 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. |
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.