organic compounds
(1-Acetyl-2,6-diphenylpiperidin-4-ylidene)(phenyl)acetonitrile
aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India, bPG Department of Physics, Rajah Serfoji Govt. College (Autonomous), Thanjavur 613 005, Tamilnadu, India, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: athiru@vsnl.net
In the title molecule, C27H24N2O, the piperidine ring adopts a boat conformation. The acetyl group at position 1 has a bisectional orientation. The two phenyl rings attached to the piperidine ring at positions 2 and 6 have bisectional and axial orientations, respectively, and make a dihedral angle of 75.27 (10)°. The phenylacetonitrile group at position 4 has an equatorial orientation. Molecules are linked by C—H⋯N, C—H⋯O intermolecular and C—H⋯π interactions. A C—H⋯O intramolecular interaction is also found in the molecule.
Related literature
Thiruvalluvar et al. (2007) have reported the of (2,6-diphenylpiperidin-4-ylidene)(phenyl)acetonitrile, in which the piperidine ring adopts a chair conformation.
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
Supporting information
10.1107/S160053680800860X/wn2248sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680800860X/wn2248Isup2.hkl
A mixture of (2,6-diphenylpiperidin-4-ylidene)(phenyl)acetonitrile (3.5 g, 0.01 mol), acetic anhydride (2.8 ml, 0.03 mol) and trimethylamine (4.2 ml, 0.03 mol) in benzene (50 ml) was refluxed for 8-10 h. The reaction mixture was cooled to room temperature and poured into ice-cold water. The solid mass was separated by filtration, dried and recrystallized from ethanol. The yield of the isolated product was 2.16 g (55%).
The C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.95–1.00 Å and Uiso(H) = 1.2–1.5Ueq(parent atom).
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell
CrysAlis CCD (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity. | |
Fig. 2. The molecular packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted. |
C27H24N2O | Z = 2 |
Mr = 392.48 | F(000) = 416 |
Triclinic, P1 | Dx = 1.243 Mg m−3 |
Hall symbol: -P 1 | Melting point: 411 K |
a = 9.4034 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.646 (6) Å | Cell parameters from 7731 reflections |
c = 10.8860 (18) Å | θ = 4.5–32.5° |
α = 90.45 (2)° | µ = 0.08 mm−1 |
β = 99.957 (14)° | T = 200 K |
γ = 101.98 (3)° | Prism, colourless |
V = 1048.9 (7) Å3 | 0.43 × 0.37 × 0.23 mm |
Oxford Diffraction Gemini diffractometer | 2238 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.062 |
Graphite monochromator | θmax = 32.4°, θmin = 4.5° |
Detector resolution: 10.5081 pixels mm-1 | h = −14→13 |
ϕ and ω scans | k = −15→15 |
14102 measured reflections | l = −16→14 |
6736 independent reflections |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 0.86 | w = 1/[σ2(Fo2) + (0.0581P)2] where P = (Fo2 + 2Fc2)/3 |
6736 reflections | (Δ/σ)max < 0.001 |
271 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C27H24N2O | γ = 101.98 (3)° |
Mr = 392.48 | V = 1048.9 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.4034 (17) Å | Mo Kα radiation |
b = 10.646 (6) Å | µ = 0.08 mm−1 |
c = 10.8860 (18) Å | T = 200 K |
α = 90.45 (2)° | 0.43 × 0.37 × 0.23 mm |
β = 99.957 (14)° |
Oxford Diffraction Gemini diffractometer | 2238 reflections with I > 2σ(I) |
14102 measured reflections | Rint = 0.062 |
6736 independent reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 0.86 | Δρmax = 0.17 e Å−3 |
6736 reflections | Δρmin = −0.18 e Å−3 |
271 parameters |
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 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 | ||
O11 | 0.28221 (18) | 0.44042 (15) | 0.77415 (18) | 0.0685 (7) | |
N1 | 0.39382 (16) | 0.27784 (16) | 0.73697 (15) | 0.0349 (6) | |
N16 | 0.59278 (19) | −0.19597 (17) | 0.91049 (19) | 0.0506 (7) | |
C2 | 0.52978 (19) | 0.22457 (18) | 0.75539 (19) | 0.0359 (7) | |
C3 | 0.49051 (19) | 0.07647 (18) | 0.7407 (2) | 0.0360 (7) | |
C4 | 0.36419 (19) | 0.01309 (19) | 0.80179 (18) | 0.0328 (6) | |
C5 | 0.2347 (2) | 0.07931 (19) | 0.7838 (2) | 0.0398 (7) | |
C6 | 0.24863 (19) | 0.19042 (18) | 0.69692 (19) | 0.0342 (7) | |
C11 | 0.3964 (3) | 0.3991 (2) | 0.7794 (2) | 0.0516 (9) | |
C12 | 0.5447 (3) | 0.4833 (2) | 0.8355 (3) | 0.0754 (10) | |
C14 | 0.36214 (19) | −0.09522 (18) | 0.86415 (17) | 0.0298 (6) | |
C15 | 0.4908 (2) | −0.15071 (18) | 0.8868 (2) | 0.0374 (7) | |
C21 | 0.6360 (2) | 0.27610 (18) | 0.6675 (2) | 0.0345 (7) | |
C22 | 0.5903 (2) | 0.2716 (2) | 0.5393 (2) | 0.0479 (8) | |
C23 | 0.6893 (2) | 0.3135 (2) | 0.4608 (2) | 0.0584 (9) | |
C24 | 0.8362 (2) | 0.3599 (2) | 0.5095 (3) | 0.0554 (10) | |
C25 | 0.8845 (2) | 0.3641 (2) | 0.6354 (3) | 0.0526 (9) | |
C26 | 0.7842 (2) | 0.32381 (19) | 0.7149 (2) | 0.0440 (7) | |
C41 | 0.23021 (19) | −0.16901 (18) | 0.91288 (19) | 0.0325 (7) | |
C42 | 0.1746 (2) | −0.29754 (19) | 0.87607 (19) | 0.0394 (7) | |
C43 | 0.0464 (2) | −0.3626 (2) | 0.9124 (2) | 0.0479 (8) | |
C44 | −0.0256 (2) | −0.3021 (2) | 0.9879 (2) | 0.0505 (8) | |
C45 | 0.0332 (2) | −0.1759 (2) | 1.0289 (2) | 0.0485 (8) | |
C46 | 0.1591 (2) | −0.1095 (2) | 0.9908 (2) | 0.0385 (7) | |
C61 | 0.21670 (19) | 0.1583 (2) | 0.5582 (2) | 0.0360 (7) | |
C62 | 0.1943 (2) | 0.0355 (2) | 0.5061 (2) | 0.0449 (8) | |
C63 | 0.1684 (2) | 0.0136 (3) | 0.3767 (3) | 0.0568 (9) | |
C64 | 0.1629 (2) | 0.1141 (3) | 0.2993 (2) | 0.0615 (9) | |
C65 | 0.1818 (2) | 0.2372 (3) | 0.3491 (2) | 0.0593 (10) | |
C66 | 0.2075 (2) | 0.2592 (2) | 0.4772 (2) | 0.0466 (8) | |
H2 | 0.58301 | 0.24860 | 0.84282 | 0.0430* | |
H3A | 0.46581 | 0.05133 | 0.65055 | 0.0431* | |
H3B | 0.57893 | 0.04320 | 0.77637 | 0.0431* | |
H5A | 0.22351 | 0.11179 | 0.86628 | 0.0477* | |
H5B | 0.14360 | 0.01501 | 0.75020 | 0.0477* | |
H6 | 0.17358 | 0.23999 | 0.71251 | 0.0411* | |
H12A | 0.53045 | 0.56738 | 0.86194 | 0.1132* | |
H12B | 0.60930 | 0.49466 | 0.77301 | 0.1132* | |
H12C | 0.59019 | 0.44235 | 0.90790 | 0.1132* | |
H22 | 0.48916 | 0.23918 | 0.50488 | 0.0576* | |
H23 | 0.65600 | 0.31034 | 0.37307 | 0.0701* | |
H24 | 0.90419 | 0.38900 | 0.45537 | 0.0665* | |
H25 | 0.98632 | 0.39436 | 0.66885 | 0.0632* | |
H26 | 0.81777 | 0.32916 | 0.80261 | 0.0528* | |
H42 | 0.22454 | −0.34069 | 0.82602 | 0.0472* | |
H43 | 0.00736 | −0.44986 | 0.88522 | 0.0575* | |
H44 | −0.11457 | −0.34695 | 1.01136 | 0.0606* | |
H45 | −0.01332 | −0.13461 | 1.08343 | 0.0582* | |
H46 | 0.19769 | −0.02222 | 1.01816 | 0.0462* | |
H62 | 0.19645 | −0.03492 | 0.55895 | 0.0539* | |
H63 | 0.15464 | −0.07120 | 0.34214 | 0.0681* | |
H64 | 0.14607 | 0.09897 | 0.21134 | 0.0736* | |
H65 | 0.17710 | 0.30679 | 0.29547 | 0.0710* | |
H66 | 0.21918 | 0.34412 | 0.51091 | 0.0559* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0661 (10) | 0.0515 (10) | 0.0951 (14) | 0.0227 (9) | 0.0221 (10) | −0.0108 (10) |
N1 | 0.0359 (9) | 0.0358 (10) | 0.0346 (10) | 0.0086 (7) | 0.0099 (7) | −0.0008 (8) |
N16 | 0.0456 (10) | 0.0407 (11) | 0.0677 (14) | 0.0131 (9) | 0.0114 (10) | 0.0047 (10) |
C2 | 0.0304 (10) | 0.0402 (12) | 0.0383 (13) | 0.0066 (9) | 0.0108 (9) | 0.0049 (10) |
C3 | 0.0303 (10) | 0.0367 (12) | 0.0438 (13) | 0.0077 (9) | 0.0137 (9) | 0.0091 (10) |
C4 | 0.0310 (10) | 0.0365 (11) | 0.0328 (12) | 0.0059 (9) | 0.0125 (8) | 0.0041 (9) |
C5 | 0.0329 (10) | 0.0479 (13) | 0.0423 (13) | 0.0103 (10) | 0.0146 (9) | 0.0109 (11) |
C6 | 0.0292 (10) | 0.0376 (11) | 0.0397 (13) | 0.0105 (9) | 0.0121 (9) | 0.0085 (10) |
C11 | 0.0546 (14) | 0.0438 (14) | 0.0600 (17) | 0.0117 (12) | 0.0191 (12) | −0.0015 (12) |
C12 | 0.0726 (17) | 0.0482 (16) | 0.101 (2) | 0.0018 (13) | 0.0184 (16) | −0.0301 (16) |
C14 | 0.0325 (10) | 0.0347 (11) | 0.0228 (10) | 0.0075 (9) | 0.0061 (8) | 0.0022 (9) |
C15 | 0.0399 (12) | 0.0275 (11) | 0.0457 (14) | 0.0031 (10) | 0.0153 (10) | 0.0007 (10) |
C21 | 0.0335 (10) | 0.0305 (11) | 0.0414 (14) | 0.0070 (9) | 0.0116 (9) | 0.0044 (9) |
C22 | 0.0330 (11) | 0.0689 (16) | 0.0402 (14) | 0.0046 (11) | 0.0092 (10) | 0.0063 (12) |
C23 | 0.0523 (14) | 0.0773 (18) | 0.0452 (15) | 0.0045 (13) | 0.0183 (12) | 0.0131 (14) |
C24 | 0.0482 (14) | 0.0574 (16) | 0.0634 (19) | 0.0019 (11) | 0.0281 (12) | 0.0153 (13) |
C25 | 0.0355 (11) | 0.0498 (14) | 0.072 (2) | 0.0028 (10) | 0.0153 (12) | 0.0101 (13) |
C26 | 0.0364 (11) | 0.0425 (13) | 0.0510 (14) | 0.0051 (10) | 0.0054 (10) | 0.0079 (11) |
C41 | 0.0291 (10) | 0.0335 (12) | 0.0355 (12) | 0.0065 (9) | 0.0072 (9) | 0.0065 (10) |
C42 | 0.0503 (12) | 0.0353 (12) | 0.0328 (12) | 0.0053 (10) | 0.0126 (10) | 0.0031 (10) |
C43 | 0.0536 (13) | 0.0393 (13) | 0.0434 (15) | −0.0058 (11) | 0.0069 (11) | 0.0087 (11) |
C44 | 0.0375 (12) | 0.0583 (16) | 0.0519 (15) | −0.0005 (11) | 0.0096 (11) | 0.0246 (13) |
C45 | 0.0451 (12) | 0.0513 (15) | 0.0562 (15) | 0.0147 (11) | 0.0229 (11) | 0.0153 (12) |
C46 | 0.0409 (11) | 0.0354 (12) | 0.0417 (13) | 0.0081 (10) | 0.0140 (10) | 0.0088 (10) |
C61 | 0.0245 (10) | 0.0401 (12) | 0.0454 (14) | 0.0078 (9) | 0.0102 (9) | 0.0036 (11) |
C62 | 0.0332 (11) | 0.0490 (14) | 0.0524 (16) | 0.0067 (10) | 0.0097 (10) | −0.0003 (12) |
C63 | 0.0429 (13) | 0.0673 (17) | 0.0575 (18) | 0.0074 (12) | 0.0080 (12) | −0.0222 (15) |
C64 | 0.0398 (13) | 0.101 (2) | 0.0390 (15) | 0.0043 (14) | 0.0071 (11) | −0.0031 (16) |
C65 | 0.0472 (14) | 0.081 (2) | 0.0468 (17) | 0.0102 (13) | 0.0042 (12) | 0.0192 (15) |
C66 | 0.0418 (12) | 0.0504 (14) | 0.0487 (15) | 0.0116 (10) | 0.0087 (10) | 0.0068 (12) |
O11—C11 | 1.235 (3) | C62—C63 | 1.397 (4) |
N1—C2 | 1.487 (3) | C63—C64 | 1.371 (4) |
N1—C6 | 1.477 (3) | C64—C65 | 1.379 (4) |
N1—C11 | 1.362 (3) | C65—C66 | 1.383 (3) |
N16—C15 | 1.152 (3) | C2—H2 | 1.0000 |
C2—C3 | 1.543 (3) | C3—H3A | 0.9900 |
C2—C21 | 1.525 (3) | C3—H3B | 0.9900 |
C3—C4 | 1.502 (3) | C5—H5A | 0.9900 |
C4—C5 | 1.515 (3) | C5—H5B | 0.9900 |
C4—C14 | 1.341 (3) | C6—H6 | 1.0000 |
C5—C6 | 1.519 (3) | C12—H12A | 0.9800 |
C6—C61 | 1.510 (3) | C12—H12B | 0.9800 |
C11—C12 | 1.516 (4) | C12—H12C | 0.9800 |
C14—C15 | 1.439 (3) | C22—H22 | 0.9500 |
C14—C41 | 1.506 (3) | C23—H23 | 0.9500 |
C21—C22 | 1.385 (3) | C24—H24 | 0.9500 |
C21—C26 | 1.386 (3) | C25—H25 | 0.9500 |
C22—C23 | 1.380 (3) | C26—H26 | 0.9500 |
C23—C24 | 1.376 (3) | C42—H42 | 0.9500 |
C24—C25 | 1.365 (5) | C43—H43 | 0.9500 |
C25—C26 | 1.394 (3) | C44—H44 | 0.9500 |
C41—C42 | 1.389 (3) | C45—H45 | 0.9500 |
C41—C46 | 1.390 (3) | C46—H46 | 0.9500 |
C42—C43 | 1.383 (3) | C62—H62 | 0.9500 |
C43—C44 | 1.383 (3) | C63—H63 | 0.9500 |
C44—C45 | 1.381 (3) | C64—H64 | 0.9500 |
C45—C46 | 1.379 (3) | C65—H65 | 0.9500 |
C61—C62 | 1.381 (3) | C66—H66 | 0.9500 |
C61—C66 | 1.402 (3) | ||
O11···C42i | 3.398 (3) | C63···H5Bvi | 2.9700 |
O11···H6 | 2.2100 | C64···H5Bvi | 2.8800 |
O11···H25ii | 2.7600 | C65···H22 | 3.0800 |
O11···H42i | 2.5800 | C66···H22 | 2.6700 |
N16···C12iii | 3.423 (3) | H2···C12 | 2.6000 |
N1···H22 | 2.8800 | H2···H12C | 2.1600 |
N1···H66 | 2.8900 | H2···H26 | 2.3100 |
N16···H12Aiii | 2.5000 | H3A···C6 | 2.8700 |
N16···H5Aiv | 2.7500 | H3A···C22 | 2.7800 |
N16···H46iv | 2.7200 | H3A···C61 | 2.8500 |
C3···C62 | 3.390 (3) | H3A···C62 | 2.7300 |
C3···C61 | 3.244 (3) | H3A···H22 | 2.5600 |
C4···C62 | 3.371 (3) | H3A···H62 | 2.5300 |
C5···C46 | 3.107 (3) | H3B···C15 | 2.4600 |
C12···C26 | 3.501 (4) | H5A···C41 | 3.0500 |
C12···C21 | 3.196 (4) | H5A···C46 | 2.7400 |
C12···N16i | 3.423 (3) | H5A···H46 | 2.2000 |
C21···C12 | 3.196 (4) | H5A···N16iv | 2.7500 |
C22···C66 | 3.520 (3) | H5A···C45vii | 3.0400 |
C22···C61 | 3.512 (3) | H5A···H45vii | 2.2000 |
C26···C45iv | 3.570 (4) | H5B···C41 | 2.8000 |
C26···C12 | 3.501 (4) | H5B···C46 | 2.9400 |
C42···O11iii | 3.398 (3) | H5B···C62 | 2.7800 |
C43···C43v | 3.544 (4) | H5B···H62 | 2.3100 |
C45···C26iv | 3.570 (4) | H5B···C63vi | 2.9700 |
C46···C5 | 3.107 (3) | H5B···C64vi | 2.8800 |
C61···C3 | 3.244 (3) | H6···O11 | 2.2100 |
C61···C22 | 3.512 (3) | H6···H66 | 2.5300 |
C62···C3 | 3.390 (3) | H12A···N16i | 2.5000 |
C62···C62vi | 3.553 (3) | H12B···C2 | 2.8100 |
C62···C4 | 3.371 (3) | H12B···C21 | 2.6600 |
C66···C22 | 3.520 (3) | H12B···C26 | 2.8300 |
C2···H12B | 2.8100 | H12C···C2 | 2.7400 |
C2···H12C | 2.7400 | H12C···H2 | 2.1600 |
C4···H62 | 2.8200 | H22···N1 | 2.8800 |
C4···H46 | 3.0300 | H22···C61 | 2.6900 |
C5···H45vii | 2.8800 | H22···C65 | 3.0800 |
C5···H62 | 2.6600 | H22···C66 | 2.6700 |
C5···H46 | 2.8300 | H22···H3A | 2.5600 |
C6···H3A | 2.8700 | H25···O11ix | 2.7600 |
C11···H66 | 3.0900 | H26···H2 | 2.3100 |
C12···H2 | 2.6000 | H26···C44iv | 2.7900 |
C15···H42 | 2.8500 | H26···C45iv | 2.8500 |
C15···H3B | 2.4600 | H42···O11iii | 2.5800 |
C21···H12B | 2.6600 | H42···C15 | 2.8500 |
C22···H3A | 2.7800 | H43···C43v | 3.0200 |
C25···H63viii | 3.0800 | H43···C44v | 3.0100 |
C26···H63viii | 2.9500 | H45···C5vii | 2.8800 |
C26···H12B | 2.8300 | H45···H5Avii | 2.2000 |
C41···H5B | 2.8000 | H46···C4 | 3.0300 |
C41···H5A | 3.0500 | H46···C5 | 2.8300 |
C43···H65vi | 2.9600 | H46···H5A | 2.2000 |
C43···H43v | 3.0200 | H46···N16iv | 2.7200 |
C44···H26iv | 2.7900 | H62···C4 | 2.8200 |
C44···H43v | 3.0100 | H62···C5 | 2.6600 |
C45···H64vi | 3.0700 | H62···H3A | 2.5300 |
C45···H5Avii | 3.0400 | H62···H5B | 2.3100 |
C45···H26iv | 2.8500 | H63···C25viii | 3.0800 |
C46···H5A | 2.7400 | H63···C26viii | 2.9500 |
C46···H5B | 2.9400 | H64···C45vi | 3.0700 |
C61···H22 | 2.6900 | H65···C43vi | 2.9600 |
C61···H3A | 2.8500 | H66···N1 | 2.8900 |
C62···H5B | 2.7800 | H66···C11 | 3.0900 |
C62···H3A | 2.7300 | H66···H6 | 2.5300 |
C2—N1—C6 | 119.34 (15) | C2—C3—H3B | 109.00 |
C2—N1—C11 | 121.28 (18) | C4—C3—H3A | 109.00 |
C6—N1—C11 | 118.09 (18) | C4—C3—H3B | 109.00 |
N1—C2—C3 | 110.80 (15) | H3A—C3—H3B | 108.00 |
N1—C2—C21 | 113.88 (16) | C4—C5—H5A | 109.00 |
C3—C2—C21 | 108.75 (16) | C4—C5—H5B | 109.00 |
C2—C3—C4 | 114.81 (16) | C6—C5—H5A | 109.00 |
C3—C4—C5 | 114.37 (17) | C6—C5—H5B | 109.00 |
C3—C4—C14 | 123.67 (17) | H5A—C5—H5B | 108.00 |
C5—C4—C14 | 121.93 (18) | N1—C6—H6 | 106.00 |
C4—C5—C6 | 114.44 (17) | C5—C6—H6 | 106.00 |
N1—C6—C5 | 108.81 (16) | C61—C6—H6 | 106.00 |
N1—C6—C61 | 112.14 (16) | C11—C12—H12A | 109.00 |
C5—C6—C61 | 117.64 (17) | C11—C12—H12B | 110.00 |
O11—C11—N1 | 121.8 (2) | C11—C12—H12C | 109.00 |
O11—C11—C12 | 120.1 (2) | H12A—C12—H12B | 109.00 |
N1—C11—C12 | 118.1 (2) | H12A—C12—H12C | 109.00 |
C4—C14—C15 | 120.42 (18) | H12B—C12—H12C | 109.00 |
C4—C14—C41 | 124.59 (17) | C21—C22—H22 | 119.00 |
C15—C14—C41 | 114.99 (16) | C23—C22—H22 | 120.00 |
N16—C15—C14 | 176.9 (2) | C22—C23—H23 | 120.00 |
C2—C21—C22 | 121.85 (18) | C24—C23—H23 | 120.00 |
C2—C21—C26 | 119.99 (19) | C23—C24—H24 | 120.00 |
C22—C21—C26 | 118.10 (19) | C25—C24—H24 | 120.00 |
C21—C22—C23 | 121.06 (19) | C24—C25—H25 | 120.00 |
C22—C23—C24 | 120.0 (2) | C26—C25—H25 | 120.00 |
C23—C24—C25 | 120.1 (2) | C21—C26—H26 | 120.00 |
C24—C25—C26 | 119.9 (2) | C25—C26—H26 | 120.00 |
C21—C26—C25 | 120.8 (2) | C41—C42—H42 | 120.00 |
C14—C41—C42 | 119.79 (17) | C43—C42—H42 | 120.00 |
C14—C41—C46 | 121.13 (17) | C42—C43—H43 | 120.00 |
C42—C41—C46 | 119.04 (18) | C44—C43—H43 | 120.00 |
C41—C42—C43 | 119.87 (19) | C43—C44—H44 | 120.00 |
C42—C43—C44 | 120.78 (19) | C45—C44—H44 | 120.00 |
C43—C44—C45 | 119.32 (19) | C44—C45—H45 | 120.00 |
C44—C45—C46 | 120.22 (19) | C46—C45—H45 | 120.00 |
C41—C46—C45 | 120.68 (19) | C41—C46—H46 | 120.00 |
C6—C61—C62 | 124.09 (19) | C45—C46—H46 | 120.00 |
C6—C61—C66 | 117.97 (18) | C61—C62—H62 | 120.00 |
C62—C61—C66 | 117.9 (2) | C63—C62—H62 | 120.00 |
C61—C62—C63 | 120.8 (2) | C62—C63—H63 | 120.00 |
C62—C63—C64 | 120.2 (3) | C64—C63—H63 | 120.00 |
C63—C64—C65 | 120.0 (2) | C63—C64—H64 | 120.00 |
C64—C65—C66 | 119.9 (2) | C65—C64—H64 | 120.00 |
C61—C66—C65 | 121.1 (2) | C64—C65—H65 | 120.00 |
N1—C2—H2 | 108.00 | C66—C65—H65 | 120.00 |
C3—C2—H2 | 108.00 | C61—C66—H66 | 119.00 |
C21—C2—H2 | 108.00 | C65—C66—H66 | 119.00 |
C2—C3—H3A | 109.00 | ||
C6—N1—C2—C3 | −5.9 (2) | C5—C6—C61—C62 | −8.6 (3) |
C6—N1—C2—C21 | 117.10 (19) | C5—C6—C61—C66 | 170.61 (17) |
C11—N1—C2—C3 | 160.88 (18) | C4—C14—C41—C42 | 123.0 (2) |
C11—N1—C2—C21 | −76.2 (2) | C4—C14—C41—C46 | −54.6 (3) |
C2—N1—C6—C5 | 51.9 (2) | C15—C14—C41—C42 | −55.8 (3) |
C2—N1—C6—C61 | −80.0 (2) | C15—C14—C41—C46 | 126.6 (2) |
C11—N1—C6—C5 | −115.26 (19) | C2—C21—C22—C23 | −177.12 (19) |
C11—N1—C6—C61 | 112.9 (2) | C26—C21—C22—C23 | −0.1 (3) |
C2—N1—C11—O11 | −173.7 (2) | C2—C21—C26—C25 | 176.10 (18) |
C2—N1—C11—C12 | 5.6 (3) | C22—C21—C26—C25 | −1.0 (3) |
C6—N1—C11—O11 | −6.8 (3) | C21—C22—C23—C24 | 0.4 (3) |
C6—N1—C11—C12 | 172.5 (2) | C22—C23—C24—C25 | 0.3 (3) |
N1—C2—C3—C4 | −42.5 (2) | C23—C24—C25—C26 | −1.4 (3) |
C21—C2—C3—C4 | −168.35 (17) | C24—C25—C26—C21 | 1.7 (3) |
N1—C2—C21—C22 | −53.0 (2) | C14—C41—C42—C43 | −174.69 (19) |
N1—C2—C21—C26 | 130.00 (19) | C46—C41—C42—C43 | 2.9 (3) |
C3—C2—C21—C22 | 71.1 (2) | C14—C41—C46—C45 | 176.11 (19) |
C3—C2—C21—C26 | −105.9 (2) | C42—C41—C46—C45 | −1.5 (3) |
C2—C3—C4—C5 | 42.4 (2) | C41—C42—C43—C44 | −1.7 (3) |
C2—C3—C4—C14 | −139.6 (2) | C42—C43—C44—C45 | −1.1 (3) |
C3—C4—C5—C6 | 5.6 (2) | C43—C44—C45—C46 | 2.6 (3) |
C14—C4—C5—C6 | −172.45 (18) | C44—C45—C46—C41 | −1.3 (3) |
C3—C4—C14—C15 | 6.4 (3) | C6—C61—C62—C63 | −178.61 (19) |
C3—C4—C14—C41 | −172.37 (18) | C66—C61—C62—C63 | 2.2 (3) |
C5—C4—C14—C15 | −175.75 (18) | C6—C61—C66—C65 | 178.57 (18) |
C5—C4—C14—C41 | 5.5 (3) | C62—C61—C66—C65 | −2.2 (3) |
C4—C5—C6—N1 | −50.8 (2) | C61—C62—C63—C64 | −0.9 (3) |
C4—C5—C6—C61 | 78.1 (2) | C62—C63—C64—C65 | −0.5 (3) |
N1—C6—C61—C62 | 118.7 (2) | C63—C64—C65—C66 | 0.5 (3) |
N1—C6—C61—C66 | −62.1 (2) | C64—C65—C66—C61 | 0.8 (3) |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) x, y−1, z; (iv) −x+1, −y, −z+2; (v) −x, −y−1, −z+2; (vi) −x, −y, −z+1; (vii) −x, −y, −z+2; (viii) −x+1, −y, −z+1; (ix) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O11 | 1.00 | 2.21 | 2.723 (3) | 110 |
C12—H12A···N16i | 0.98 | 2.50 | 3.423 (3) | 158 |
C42—H42···O11iii | 0.95 | 2.58 | 3.398 (3) | 145 |
C22—H22···Cg1 | 0.95 | 2.79 | 3.734 (3) | 174 |
C26—H26···Cg2iv | 0.95 | 2.89 | 3.784 (3) | 157 |
Symmetry codes: (i) x, y+1, z; (iii) x, y−1, z; (iv) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C27H24N2O |
Mr | 392.48 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 200 |
a, b, c (Å) | 9.4034 (17), 10.646 (6), 10.8860 (18) |
α, β, γ (°) | 90.45 (2), 99.957 (14), 101.98 (3) |
V (Å3) | 1048.9 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.43 × 0.37 × 0.23 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14102, 6736, 2238 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.755 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.151, 0.86 |
No. of reflections | 6736 |
No. of parameters | 271 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.18 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O11 | 1.00 | 2.21 | 2.723 (3) | 110 |
C12—H12A···N16i | 0.98 | 2.50 | 3.423 (3) | 158 |
C42—H42···O11ii | 0.95 | 2.58 | 3.398 (3) | 145 |
C22—H22···Cg1 | 0.95 | 2.79 | 3.734 (3) | 174 |
C26—H26···Cg2iii | 0.95 | 2.89 | 3.784 (3) | 157 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+1, −y, −z+2. |
Acknowledgements
RJB acknowledges the NSF-MRI program for funding the purchase of the X-ray CCD diffractometer. AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007].
References
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thiruvalluvar, A., Balamurugan, S., Manimekalai, A. & Balamurugan, A. (2007). Acta Cryst. E63, o2903. Web of Science CSD CrossRef IUCr Journals Google Scholar
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In the title compound, (Fig. 1), the piperidine ring adopts a boat conformation. The acetyl group at position 1 has a bisectional orientation. The two phenyl rings attached to the piperidine ring at positions 2 and 6 have bisectional and axial orientations, respectively, and make a dihedral angle of 75.27 (10)°. The phenyl-acetonitrile group at position 4 has an equatorial orientation. Molecules are linked by intermolecular C12—H12A···N16, C42—H42···O11 and intramolecular C6—H6···O11 hydrogen bonds. There are C22—H22···π (x, y, z) interactions involving the phenyl ring at 6 and C26—H26···π (1 - x, -y, 2 - z) interactions involving the phenyl ring at C14.