organic compounds
of (4-hydroxypiperidin-1-yl)[4-(trifluoromethyl)phenyl]methanone
aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, bDepartment of Chemistry, Madras Christian College, Chennai-59, India, cSCRI, Anna Hospital Campus, Chennai-106, Tamilnadu, India, and dAnna Siddha Medical College, Chennai-106, Tamilnadu, India
*Correspondence e-mail: guqmc@yahoo.com
The title compound, C13H14NO2F3, crystallises with two molecules, A and B, in the with similar conformations. The dihedral angles between the piperidine and phenyl rings are 83.76 (2) and 75.23 (2)° in molecules A and B, respectively. The bond-angle sums around the N atoms [359.1 and 359.7° for molecules A and B, respectively] indicate sp2 for these atoms. In the crystal, O—H⋯O hydrogen bonds link the molecules into separate [100] chains of A and B molecules. The chains are cross-linked by C—H⋯O interactions, generating alternating (001) sheets of A and B molecules.
Keywords: crystal structure; piperdine derivative; hydrogen bonding.
CCDC reference: 1425996
1. Related literature
For the synthesis, see: Revathi et al. (2015). For the biological activities of piperdine derivatives, see: Ramalingan et al. (2004); Ramachandran et al. (2011); Lee et al. (2001); Parthiban et al. (2005). For a related structure, see: Prathebha et al. (2015).
2. Experimental
2.1. Crystal data
|
2.3. Refinement
|
Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; 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); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 1425996
10.1107/S205698901501765X/hb7494sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S205698901501765X/hb7494Isup2.hkl
Supporting information file. DOI: 10.1107/S205698901501765X/hb7494Isup3.cml
The title compound was synthesized following a published procedure (Revathi et al., 2015). In a 250 ml round-bottomed flask, 100 ml of ethylmethylketone was added to 4-hydroxypiperidiene (0.03 mol) and stirred at room temperature. After a span of about 5 min, triethylamine (0.03 mol) was added and the mixture was stirred for a time frame of 10 min. 4-Trifloromethylbenzoyl chloride (0.03 mol) was added and the reaction mixture was stirred at room temperature for about 2 h. A white precipitate of triethylammonium chloride was produced, which was filtered and the filtrate was evaporated to get the crude product. Two recrystallizations from ethylmethylketone solution gave colourless blocks of the title compound (yield: 87%).
Hydrogen atoms other then hydroxy H atoms were positioned geometrically and treated as riding on their parent atoms and hydroxy H-atoms were located from difference Fourier maps and refined with,C—H distance of 0.93–0.98 Å, with Uiso(H)= 1.5 Ueq(c-methyl), Uiso(H)= 1.2Ueq(C,O) for other H atom.
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. | |
Fig. 2. The packing of the molecules in the crystal structure. The dashed lines indicate the hydrogen bonds. |
C13H14F3NO2 | F(000) = 1136 |
Mr = 273.25 | Dx = 1.432 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | θ = 1.8–25.7° |
a = 16.1328 (14) Å | µ = 0.13 mm−1 |
b = 6.8283 (6) Å | T = 293 K |
c = 23.017 (2) Å | Block, colorless |
V = 2535.5 (4) Å3 | 0.35 × 0.30 × 0.25 mm |
Z = 8 |
Bruker Kappa APEXII CCD diffractometer | 4823 independent reflections |
Radiation source: fine-focus sealed tube | 2950 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
ω and φ scans | θmax = 25.7°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −19→19 |
Tmin = 0.957, Tmax = 0.969 | k = −8→7 |
26641 measured reflections | l = −28→28 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.190 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0905P)2 + 1.4379P] where P = (Fo2 + 2Fc2)/3 |
4823 reflections | (Δ/σ)max < 0.001 |
343 parameters | Δρmax = 0.27 e Å−3 |
1 restraint | Δρmin = −0.26 e Å−3 |
C13H14F3NO2 | V = 2535.5 (4) Å3 |
Mr = 273.25 | Z = 8 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 16.1328 (14) Å | µ = 0.13 mm−1 |
b = 6.8283 (6) Å | T = 293 K |
c = 23.017 (2) Å | 0.35 × 0.30 × 0.25 mm |
Bruker Kappa APEXII CCD diffractometer | 4823 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2950 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.969 | Rint = 0.046 |
26641 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 1 restraint |
wR(F2) = 0.190 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.27 e Å−3 |
4823 reflections | Δρmin = −0.26 e Å−3 |
343 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 | ||
C10 | 1.0836 (3) | 0.3171 (9) | 0.0067 (2) | 0.0622 (13) | |
H1 | 1.1181 | 0.4072 | 0.0294 | 0.075* | |
C9 | 1.0108 (3) | 0.4279 (8) | −0.0181 (3) | 0.0649 (14) | |
H2A | 0.9844 | 0.5021 | 0.0127 | 0.078* | |
H2B | 1.0308 | 0.5203 | −0.0469 | 0.078* | |
C8 | 0.9480 (3) | 0.2956 (8) | −0.0457 (2) | 0.0593 (13) | |
H3A | 0.9008 | 0.3719 | −0.0587 | 0.071* | |
H3B | 0.9722 | 0.2316 | −0.0793 | 0.071* | |
C12 | 0.9885 (3) | 0.0264 (7) | 0.0177 (2) | 0.0523 (11) | |
H4A | 1.0121 | −0.0478 | −0.0142 | 0.063* | |
H4B | 0.9673 | −0.0657 | 0.0462 | 0.063* | |
C11 | 1.0551 (3) | 0.1530 (8) | 0.0453 (2) | 0.0580 (13) | |
H5A | 1.0338 | 0.2078 | 0.0812 | 0.070* | |
H5B | 1.1023 | 0.0714 | 0.0550 | 0.070* | |
C7 | 0.8449 (3) | 0.1543 (6) | 0.0173 (2) | 0.0448 (10) | |
C1 | 0.8174 (3) | 0.0056 (7) | 0.06151 (19) | 0.0450 (11) | |
C2 | 0.8144 (3) | −0.1940 (7) | 0.0494 (2) | 0.0495 (11) | |
H8 | 0.8348 | −0.2411 | 0.0142 | 0.059* | |
C3 | 0.7815 (3) | −0.3204 (7) | 0.0891 (2) | 0.0485 (11) | |
H9 | 0.7780 | −0.4530 | 0.0802 | 0.058* | |
C4 | 0.7532 (3) | −0.2536 (7) | 0.1427 (2) | 0.0502 (12) | |
C5 | 0.7564 (3) | −0.0557 (7) | 0.1542 (2) | 0.0606 (13) | |
H11 | 0.7372 | −0.0091 | 0.1897 | 0.073* | |
C6 | 0.7873 (3) | 0.0733 (7) | 0.1142 (2) | 0.0570 (13) | |
H12 | 0.7881 | 0.2066 | 0.1224 | 0.068* | |
C13 | 0.7202 (3) | −0.3921 (7) | 0.1854 (2) | 0.0589 (12) | |
C23 | 0.6591 (3) | 0.3211 (8) | 0.3540 (2) | 0.0612 (13) | |
H14 | 0.6260 | 0.4154 | 0.3318 | 0.073* | |
C22 | 0.6845 (3) | 0.1537 (8) | 0.3146 (2) | 0.0602 (13) | |
H15A | 0.7085 | 0.2067 | 0.2794 | 0.072* | |
H15B | 0.6355 | 0.0795 | 0.3039 | 0.072* | |
C21 | 0.7469 (3) | 0.0165 (7) | 0.3433 (2) | 0.0577 (13) | |
H16A | 0.7206 | −0.0528 | 0.3752 | 0.069* | |
H16B | 0.7661 | −0.0795 | 0.3153 | 0.069* | |
C25 | 0.7932 (3) | 0.2784 (9) | 0.4071 (3) | 0.0730 (17) | |
H17A | 0.8421 | 0.3465 | 0.4209 | 0.088* | |
H17B | 0.7660 | 0.2179 | 0.4401 | 0.088* | |
C24 | 0.7348 (3) | 0.4220 (8) | 0.3779 (3) | 0.0737 (16) | |
H18A | 0.7179 | 0.5205 | 0.4058 | 0.088* | |
H18B | 0.7638 | 0.4878 | 0.3465 | 0.088* | |
C20 | 0.8949 (3) | 0.1163 (8) | 0.3466 (2) | 0.0552 (12) | |
C17 | 0.9167 (3) | −0.0342 (7) | 0.3019 (2) | 0.0492 (11) | |
C18 | 0.9246 (3) | −0.2314 (8) | 0.3153 (2) | 0.0548 (13) | |
H21 | 0.9102 | −0.2764 | 0.3521 | 0.066* | |
C19 | 0.9537 (3) | −0.3609 (7) | 0.2742 (2) | 0.0574 (12) | |
H22 | 0.9605 | −0.4926 | 0.2833 | 0.069* | |
C14 | 0.9728 (3) | −0.2926 (7) | 0.2193 (2) | 0.0528 (12) | |
C15 | 0.9639 (3) | −0.1019 (8) | 0.2054 (2) | 0.0688 (15) | |
H24 | 0.9766 | −0.0586 | 0.1681 | 0.083* | |
C16 | 0.9363 (4) | 0.0281 (8) | 0.2465 (2) | 0.0688 (15) | |
H25 | 0.9306 | 0.1597 | 0.2369 | 0.083* | |
C26 | 1.0021 (3) | −0.4353 (8) | 0.1751 (2) | 0.0635 (14) | |
N1 | 0.9207 (2) | 0.1482 (6) | −0.00380 (16) | 0.0494 (10) | |
N2 | 0.8169 (2) | 0.1289 (7) | 0.36505 (17) | 0.0552 (11) | |
O2 | 1.13070 (19) | 0.2418 (6) | −0.04018 (18) | 0.0719 (11) | |
H1A | 1.1781 | 0.2194 | −0.0292 | 0.108* | |
O1 | 0.79406 (18) | 0.2827 (5) | 0.00270 (16) | 0.0574 (9) | |
O4 | 0.6124 (2) | 0.2524 (6) | 0.40139 (18) | 0.0712 (10) | |
H3 | 0.5629 | 0.2553 | 0.3932 | 0.107* | |
O3 | 0.9492 (2) | 0.2285 (7) | 0.36352 (19) | 0.0842 (14) | |
F1 | 0.6669 (2) | −0.5173 (6) | 0.16460 (16) | 0.1029 (13) | |
F2 | 0.6821 (3) | −0.3078 (6) | 0.22995 (16) | 0.1089 (14) | |
F3 | 0.7790 (2) | −0.5065 (6) | 0.20861 (18) | 0.1101 (14) | |
F4 | 1.0566 (2) | −0.5623 (6) | 0.19448 (16) | 0.1038 (13) | |
F5 | 1.0359 (3) | −0.3537 (6) | 0.12899 (16) | 0.1165 (15) | |
F6 | 0.9416 (2) | −0.5492 (6) | 0.15396 (18) | 0.1028 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C10 | 0.044 (3) | 0.079 (3) | 0.063 (3) | −0.006 (3) | 0.005 (3) | 0.000 (3) |
C9 | 0.047 (3) | 0.063 (3) | 0.085 (4) | −0.002 (2) | 0.001 (3) | 0.020 (3) |
C8 | 0.041 (3) | 0.080 (3) | 0.057 (3) | 0.003 (2) | 0.001 (2) | 0.028 (3) |
C12 | 0.046 (2) | 0.054 (3) | 0.057 (3) | 0.014 (2) | 0.003 (2) | 0.010 (2) |
C11 | 0.044 (3) | 0.080 (3) | 0.050 (3) | 0.010 (2) | −0.002 (2) | 0.011 (3) |
C7 | 0.037 (2) | 0.048 (2) | 0.049 (3) | −0.003 (2) | −0.003 (2) | 0.000 (2) |
C1 | 0.039 (2) | 0.049 (3) | 0.047 (3) | −0.005 (2) | 0.002 (2) | −0.002 (2) |
C2 | 0.052 (3) | 0.054 (3) | 0.042 (3) | −0.001 (2) | 0.004 (2) | −0.001 (2) |
C3 | 0.054 (3) | 0.043 (2) | 0.048 (3) | −0.005 (2) | 0.003 (2) | −0.007 (2) |
C4 | 0.042 (3) | 0.064 (3) | 0.044 (3) | −0.008 (2) | 0.001 (2) | 0.001 (2) |
C5 | 0.071 (3) | 0.057 (3) | 0.055 (3) | −0.012 (3) | 0.015 (3) | −0.008 (3) |
C6 | 0.069 (3) | 0.047 (3) | 0.054 (3) | −0.003 (2) | 0.013 (2) | −0.008 (2) |
C13 | 0.061 (3) | 0.063 (3) | 0.052 (3) | −0.008 (3) | 0.002 (2) | 0.001 (3) |
C23 | 0.048 (3) | 0.077 (3) | 0.058 (3) | −0.003 (3) | 0.001 (3) | 0.001 (3) |
C22 | 0.049 (3) | 0.075 (3) | 0.056 (3) | −0.008 (2) | −0.001 (2) | −0.009 (3) |
C21 | 0.041 (3) | 0.065 (3) | 0.067 (3) | −0.014 (2) | 0.002 (2) | −0.014 (3) |
C25 | 0.046 (3) | 0.102 (4) | 0.071 (4) | 0.003 (3) | −0.005 (3) | −0.044 (4) |
C24 | 0.062 (3) | 0.067 (3) | 0.093 (4) | −0.009 (3) | 0.019 (3) | −0.027 (3) |
C20 | 0.038 (2) | 0.072 (3) | 0.056 (3) | 0.000 (2) | −0.004 (2) | −0.016 (3) |
C17 | 0.034 (2) | 0.061 (3) | 0.052 (3) | 0.000 (2) | 0.002 (2) | −0.008 (2) |
C18 | 0.050 (3) | 0.068 (3) | 0.046 (3) | −0.013 (2) | 0.004 (2) | −0.006 (2) |
C19 | 0.065 (3) | 0.054 (3) | 0.053 (3) | −0.003 (2) | −0.002 (2) | −0.002 (3) |
C14 | 0.045 (2) | 0.066 (3) | 0.047 (3) | 0.008 (2) | 0.006 (2) | −0.005 (2) |
C15 | 0.080 (4) | 0.078 (4) | 0.048 (3) | 0.008 (3) | 0.017 (3) | 0.001 (3) |
C16 | 0.089 (4) | 0.055 (3) | 0.062 (3) | 0.008 (3) | 0.013 (3) | 0.002 (3) |
C26 | 0.057 (3) | 0.071 (3) | 0.063 (3) | 0.010 (3) | 0.003 (3) | −0.012 (3) |
N1 | 0.040 (2) | 0.058 (2) | 0.050 (2) | 0.0036 (18) | 0.0025 (17) | 0.0156 (19) |
N2 | 0.034 (2) | 0.076 (3) | 0.056 (3) | −0.0026 (18) | 0.0028 (17) | −0.026 (2) |
O2 | 0.0471 (19) | 0.108 (3) | 0.061 (2) | 0.003 (2) | 0.0028 (17) | 0.005 (2) |
O1 | 0.0420 (18) | 0.059 (2) | 0.071 (2) | 0.0078 (15) | 0.0006 (16) | 0.0096 (17) |
O4 | 0.0499 (19) | 0.096 (3) | 0.067 (3) | −0.0026 (19) | 0.0084 (18) | 0.006 (2) |
O3 | 0.0412 (18) | 0.107 (3) | 0.105 (3) | −0.013 (2) | −0.0003 (19) | −0.053 (3) |
F1 | 0.110 (3) | 0.116 (3) | 0.082 (2) | −0.065 (2) | −0.004 (2) | 0.014 (2) |
F2 | 0.155 (4) | 0.095 (2) | 0.076 (2) | −0.016 (2) | 0.057 (2) | 0.002 (2) |
F3 | 0.087 (2) | 0.127 (3) | 0.116 (3) | 0.004 (2) | 0.009 (2) | 0.069 (3) |
F4 | 0.097 (3) | 0.119 (3) | 0.096 (3) | 0.053 (2) | −0.008 (2) | −0.029 (2) |
F5 | 0.168 (4) | 0.109 (3) | 0.072 (2) | 0.004 (3) | 0.060 (3) | −0.012 (2) |
F6 | 0.079 (2) | 0.119 (3) | 0.110 (3) | 0.003 (2) | 0.001 (2) | −0.059 (3) |
C10—O2 | 1.417 (7) | C23—C24 | 1.508 (7) |
C10—C11 | 1.501 (8) | C23—C22 | 1.514 (7) |
C10—C9 | 1.509 (7) | C23—H14 | 0.9800 |
C10—H1 | 0.9800 | C22—C21 | 1.526 (7) |
C9—C8 | 1.499 (8) | C22—H15A | 0.9700 |
C9—H2A | 0.9700 | C22—H15B | 0.9700 |
C9—H2B | 0.9700 | C21—N2 | 1.455 (6) |
C8—N1 | 1.462 (6) | C21—H16A | 0.9700 |
C8—H3A | 0.9700 | C21—H16B | 0.9700 |
C8—H3B | 0.9700 | C25—N2 | 1.457 (6) |
C12—N1 | 1.460 (6) | C25—C24 | 1.516 (9) |
C12—C11 | 1.519 (7) | C25—H17A | 0.9700 |
C12—H4A | 0.9700 | C25—H17B | 0.9700 |
C12—H4B | 0.9700 | C24—H18A | 0.9700 |
C11—H5A | 0.9700 | C24—H18B | 0.9700 |
C11—H5B | 0.9700 | C20—O3 | 1.228 (6) |
C7—O1 | 1.247 (5) | C20—N2 | 1.330 (6) |
C7—N1 | 1.316 (6) | C20—C17 | 1.496 (7) |
C7—C1 | 1.505 (6) | C17—C16 | 1.381 (8) |
C1—C6 | 1.386 (6) | C17—C18 | 1.387 (7) |
C1—C2 | 1.392 (7) | C18—C19 | 1.378 (7) |
C2—C3 | 1.364 (7) | C18—H21 | 0.9300 |
C2—H8 | 0.9300 | C19—C14 | 1.380 (7) |
C3—C4 | 1.394 (7) | C19—H22 | 0.9300 |
C3—H9 | 0.9300 | C14—C15 | 1.349 (7) |
C4—C5 | 1.378 (7) | C14—C26 | 1.486 (7) |
C4—C13 | 1.464 (7) | C15—C16 | 1.372 (7) |
C5—C6 | 1.368 (7) | C15—H24 | 0.9300 |
C5—H11 | 0.9300 | C16—H25 | 0.9300 |
C6—H12 | 0.9300 | C26—F4 | 1.313 (6) |
C13—F1 | 1.304 (6) | C26—F5 | 1.317 (7) |
C13—F2 | 1.327 (6) | C26—F6 | 1.339 (6) |
C13—F3 | 1.339 (6) | O2—H1A | 0.8200 |
C23—O4 | 1.407 (6) | O4—H3 | 0.8200 |
O2—C10—C11 | 110.1 (5) | C24—C23—H14 | 109.4 |
O2—C10—C9 | 108.1 (5) | C22—C23—H14 | 109.4 |
C11—C10—C9 | 111.1 (4) | C23—C22—C21 | 112.6 (4) |
O2—C10—H1 | 109.2 | C23—C22—H15A | 109.1 |
C11—C10—H1 | 109.2 | C21—C22—H15A | 109.1 |
C9—C10—H1 | 109.2 | C23—C22—H15B | 109.1 |
C8—C9—C10 | 112.6 (5) | C21—C22—H15B | 109.1 |
C8—C9—H2A | 109.1 | H15A—C22—H15B | 107.8 |
C10—C9—H2A | 109.1 | N2—C21—C22 | 109.7 (4) |
C8—C9—H2B | 109.1 | N2—C21—H16A | 109.7 |
C10—C9—H2B | 109.1 | C22—C21—H16A | 109.7 |
H2A—C9—H2B | 107.8 | N2—C21—H16B | 109.7 |
N1—C8—C9 | 109.8 (4) | C22—C21—H16B | 109.7 |
N1—C8—H3A | 109.7 | H16A—C21—H16B | 108.2 |
C9—C8—H3A | 109.7 | N2—C25—C24 | 108.8 (5) |
N1—C8—H3B | 109.7 | N2—C25—H17A | 109.9 |
C9—C8—H3B | 109.7 | C24—C25—H17A | 109.9 |
H3A—C8—H3B | 108.2 | N2—C25—H17B | 109.9 |
N1—C12—C11 | 110.3 (4) | C24—C25—H17B | 109.9 |
N1—C12—H4A | 109.6 | H17A—C25—H17B | 108.3 |
C11—C12—H4A | 109.6 | C23—C24—C25 | 111.7 (5) |
N1—C12—H4B | 109.6 | C23—C24—H18A | 109.3 |
C11—C12—H4B | 109.6 | C25—C24—H18A | 109.3 |
H4A—C12—H4B | 108.1 | C23—C24—H18B | 109.3 |
C10—C11—C12 | 113.2 (4) | C25—C24—H18B | 109.3 |
C10—C11—H5A | 108.9 | H18A—C24—H18B | 107.9 |
C12—C11—H5A | 108.9 | O3—C20—N2 | 122.3 (4) |
C10—C11—H5B | 108.9 | O3—C20—C17 | 118.5 (4) |
C12—C11—H5B | 108.9 | N2—C20—C17 | 119.1 (4) |
H5A—C11—H5B | 107.7 | C16—C17—C18 | 118.8 (5) |
O1—C7—N1 | 122.3 (4) | C16—C17—C20 | 118.5 (5) |
O1—C7—C1 | 117.6 (4) | C18—C17—C20 | 122.4 (5) |
N1—C7—C1 | 120.1 (4) | C19—C18—C17 | 120.2 (5) |
C6—C1—C2 | 119.3 (4) | C19—C18—H21 | 119.9 |
C6—C1—C7 | 118.1 (4) | C17—C18—H21 | 119.9 |
C2—C1—C7 | 122.4 (4) | C18—C19—C14 | 119.2 (5) |
C3—C2—C1 | 119.9 (5) | C18—C19—H22 | 120.4 |
C3—C2—H8 | 120.0 | C14—C19—H22 | 120.4 |
C1—C2—H8 | 120.0 | C15—C14—C19 | 121.3 (5) |
C2—C3—C4 | 120.9 (4) | C15—C14—C26 | 120.3 (5) |
C2—C3—H9 | 119.5 | C19—C14—C26 | 118.4 (5) |
C4—C3—H9 | 119.5 | C14—C15—C16 | 119.7 (5) |
C5—C4—C3 | 118.6 (5) | C14—C15—H24 | 120.2 |
C5—C4—C13 | 121.2 (5) | C16—C15—H24 | 120.2 |
C3—C4—C13 | 120.2 (4) | C15—C16—C17 | 120.8 (5) |
C6—C5—C4 | 121.1 (5) | C15—C16—H25 | 119.6 |
C6—C5—H11 | 119.5 | C17—C16—H25 | 119.6 |
C4—C5—H11 | 119.5 | F4—C26—F5 | 106.0 (5) |
C5—C6—C1 | 120.1 (5) | F4—C26—F6 | 103.2 (4) |
C5—C6—H12 | 119.9 | F5—C26—F6 | 104.7 (5) |
C1—C6—H12 | 119.9 | F4—C26—C14 | 114.5 (5) |
F1—C13—F2 | 105.2 (5) | F5—C26—C14 | 114.0 (5) |
F1—C13—F3 | 103.4 (4) | F6—C26—C14 | 113.4 (4) |
F2—C13—F3 | 105.8 (4) | C7—N1—C12 | 126.1 (4) |
F1—C13—C4 | 114.7 (4) | C7—N1—C8 | 120.0 (4) |
F2—C13—C4 | 114.0 (4) | C12—N1—C8 | 113.0 (4) |
F3—C13—C4 | 112.8 (4) | C20—N2—C21 | 126.2 (4) |
O4—C23—C24 | 107.6 (4) | C20—N2—C25 | 120.3 (4) |
O4—C23—C22 | 110.9 (5) | C21—N2—C25 | 113.2 (4) |
C24—C23—C22 | 110.1 (4) | C10—O2—H1A | 109.5 |
O4—C23—H14 | 109.4 | C23—O4—H3 | 109.5 |
O2—C10—C9—C8 | 70.2 (6) | O3—C20—C17—C18 | 106.8 (6) |
C11—C10—C9—C8 | −50.8 (7) | N2—C20—C17—C18 | −75.7 (6) |
C10—C9—C8—N1 | 55.5 (6) | C16—C17—C18—C19 | 1.8 (7) |
O2—C10—C11—C12 | −71.0 (5) | C20—C17—C18—C19 | −172.8 (4) |
C9—C10—C11—C12 | 48.7 (6) | C17—C18—C19—C14 | −1.7 (7) |
N1—C12—C11—C10 | −51.7 (6) | C18—C19—C14—C15 | 0.5 (8) |
O1—C7—C1—C6 | −55.1 (6) | C18—C19—C14—C26 | −178.5 (4) |
N1—C7—C1—C6 | 123.6 (5) | C19—C14—C15—C16 | 0.6 (8) |
O1—C7—C1—C2 | 119.0 (5) | C26—C14—C15—C16 | 179.5 (5) |
N1—C7—C1—C2 | −62.2 (6) | C14—C15—C16—C17 | −0.5 (9) |
C6—C1—C2—C3 | 0.4 (7) | C18—C17—C16—C15 | −0.8 (8) |
C7—C1—C2—C3 | −173.7 (4) | C20—C17—C16—C15 | 174.1 (5) |
C1—C2—C3—C4 | −2.2 (7) | C15—C14—C26—F4 | 137.5 (5) |
C2—C3—C4—C5 | 2.3 (7) | C19—C14—C26—F4 | −43.5 (7) |
C2—C3—C4—C13 | −178.3 (4) | C15—C14—C26—F5 | 15.3 (8) |
C3—C4—C5—C6 | −0.6 (8) | C19—C14—C26—F5 | −165.7 (5) |
C13—C4—C5—C6 | 180.0 (5) | C15—C14—C26—F6 | −104.4 (6) |
C4—C5—C6—C1 | −1.1 (8) | C19—C14—C26—F6 | 74.6 (6) |
C2—C1—C6—C5 | 1.2 (7) | O1—C7—N1—C12 | 168.7 (4) |
C7—C1—C6—C5 | 175.6 (4) | C1—C7—N1—C12 | −10.0 (7) |
C5—C4—C13—F1 | 132.1 (5) | O1—C7—N1—C8 | 0.2 (7) |
C3—C4—C13—F1 | −47.2 (7) | C1—C7—N1—C8 | −178.5 (4) |
C5—C4—C13—F2 | 10.8 (7) | C11—C12—N1—C7 | −111.8 (5) |
C3—C4—C13—F2 | −168.6 (5) | C11—C12—N1—C8 | 57.4 (5) |
C5—C4—C13—F3 | −109.9 (6) | C9—C8—N1—C7 | 110.3 (5) |
C3—C4—C13—F3 | 70.7 (6) | C9—C8—N1—C12 | −59.5 (6) |
O4—C23—C22—C21 | −67.9 (5) | O3—C20—N2—C21 | 173.3 (5) |
C24—C23—C22—C21 | 51.1 (6) | C17—C20—N2—C21 | −4.0 (8) |
C23—C22—C21—N2 | −53.0 (5) | O3—C20—N2—C25 | −0.5 (9) |
O4—C23—C24—C25 | 67.5 (6) | C17—C20—N2—C25 | −177.9 (5) |
C22—C23—C24—C25 | −53.5 (6) | C22—C21—N2—C20 | −115.5 (6) |
N2—C25—C24—C23 | 57.8 (6) | C22—C21—N2—C25 | 58.7 (6) |
O3—C20—C17—C16 | −67.8 (7) | C24—C25—N2—C20 | 113.5 (5) |
N2—C20—C17—C16 | 109.6 (6) | C24—C25—N2—C21 | −61.1 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1A···O1i | 0.82 | 2.01 | 2.819 (4) | 169 |
O4—H3···O3ii | 0.82 | 1.96 | 2.775 (5) | 173 |
C3—H9···O1iii | 0.93 | 2.55 | 3.367 (6) | 147 |
C18—H21···O2iv | 0.93 | 2.58 | 3.445 (7) | 156 |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x−1/2, −y+1/2, z; (iii) x, y−1, z; (iv) −x+2, −y, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1A···O1i | 0.82 | 2.01 | 2.819 (4) | 169 |
O4—H3···O3ii | 0.82 | 1.96 | 2.775 (5) | 173 |
C3—H9···O1iii | 0.93 | 2.55 | 3.367 (6) | 147 |
C18—H21···O2iv | 0.93 | 2.58 | 3.445 (7) | 156 |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x−1/2, −y+1/2, z; (iii) x, y−1, z; (iv) −x+2, −y, z+1/2. |
Acknowledgements
The authors thank Central Instrumentation Facility, Queen Mary's College, Chennai-4, for the computing facility and the SAIF, IIT, Madras, for the X-ray data-collection facility.
References
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Lee, H. K., Chun, J. S. & Pak, C. S. (2001). Tetrahedron Lett. 42, 3483–3486. Web of Science CrossRef CAS Google Scholar
Parthiban, P., Balasubramanian, S., Aridoss, G. & Kabilan, S. (2005). Med. Chem. Res. 14, 523–538. Web of Science CrossRef CAS Google Scholar
Prathebha, K., Reuben Jonathan, D., Revathi, B. K., Sathya, S. & Usha, G. (2015). Acta Cryst. E71, o39–o40. CSD CrossRef IUCr Journals Google Scholar
Ramachandran, R., Rani, M., Senthan, S., Jeong, Y.-T. & Kabilan, S. (2011). Eur. J. Med. Chem. 46, 1926–1934. Web of Science CSD CrossRef CAS PubMed Google Scholar
Ramalingan, C., Balasubramanian, S., Kabilan, S. & Vasudevan, M. (2004). Eur. J. Med. Chem. 39, 527–533. Web of Science CrossRef PubMed CAS Google Scholar
Revathi, B. K., Reuben Jonathan, D., Sathya, S., Prathebha, K. & Usha, G. (2015). Acta Cryst. E71, o359–o360. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. 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.
The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF.
The motivation for the biological trial arises as piperidine derivatives are an important class of heterocyclic compounds with potent pharmacological/ biological activities (Ramalingan et al., 2004; Ramachandran et al., 2011). Heterocycles with piperidine sub-structures are being used as synthons in the construction of alkaloid natural products (Lee et al., 2001). Piperidine derivatives exhibit a broad-spectrum of biological activities such as anti- bacterial and anti-cancer (Parthiban et al., 2005).
In the title compound,the C—N distances of piperidine ring in molecule A(C8—C12/N1) & B(C21—C25/N2) are in the range[1.318 (6)–1.462 (6) Å] and [1.329 (6)–1.458 (6) Å] are in good agreement with values of a similar reported structure (Revathi et al., 2015). The C—O distance in molecule A & B are [1.242 (6) Å & 1.227 (6) Å], it indicates double bond character and are comparable with the value reported previously (Prathebha et al., 2015). The dihedral angle between piperidine ring and phenyl ring in molecule A & B are 83.76 (2)° and 75.23 (2)°. The Piperidine rings are in equatorial (eq) orientation with the corresponding phenyl rings. The sum of the bond angles around the N1 & N2 atoms are [359.1 (4)° and 359.7 (4)°, respectively], shows sP2 hybridization of the atoms. The piperidine ring in the molecule A adopts a chair conformation with puckering parameters of q2 = 0.051 (5) Å, Phi2 = 138.01°, q3 = -0.537 (6) Å, QT = 0.539 (6) Å and theta2 = 174.53 (5)°. The piperidine ring in the molecule B adopts a chair conformation with puckering parameters of q2 = 0.048 (6) Å, Phi2 = 159.33°, q3 = -0.561 (6) Å, QT = 0.563 (6) Å and theta2 = 175.12 (6)°.