Acta Cryst. (2007). E63, o2903 [ doi:10.1107/S1600536807022386 ]
In the title molecule, C25H22N2, the piperidine ring adopts a chair conformation. The two phenyl rings attached to the piperidine ring have equatorial orientations and make a dihedral angle of 17.9 (1)°. The phenylacetonitrile group has a bisectional orientation. Molecules are linked by intramolecular C-H
N interactions, and by N-H![[pi]](/logos/entities/pi_rmgif.gif)
and C-H interactions.
The title compound was prepared following the general procedure reported by Lavagnino & Shepard (1957). A mixture of r(2),c(6)-diphenylpiperidin-4-one (2.51 g, 0.01 mol), benzylcyanide (1.15 ml, 0.01 mol) and potassium hydroxide (0.66 g, 0.01 mol) in 50 ml of absolute ethanol. The solution was heated on water bath for 2 days. Then diluted with 25 ml water and chilled in an ice bath. The solid mass which separated was filtered off, dried and recrystallized from ethanol. The yield of the isolated product was 2.09 g (60%).
The H atom bonded to N1 was located in a difference Fourier map and refined isotropically. 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) = 1.2Ueq(parent atom).
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
![[Figure 1]](./ww2085fig1thm.gif)
| Fig. 1. View of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
| C25H22N2 | Z = 2 |
| Mr = 350.45 | F(000) = 372 |
| Triclinic, P1 | Dx = 1.214 Mg m−3 |
| Hall symbol: -P 1 | Melting point: 441(1) K |
| a = 7.5687 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 11.3610 (5) Å | Cell parameters from 3245 reflections |
| c = 12.1481 (5) Å | θ = 2.0–25.0° |
| α = 111.318 (2)° | µ = 0.07 mm−1 |
| β = 92.757 (2)° | T = 160 K |
| γ = 97.920 (2)° | Plate-like, yellow |
| V = 958.36 (7) Å3 | 0.28 × 0.28 × 0.18 mm |
| Nonius KappaCCD area-detector diffractometer | 2742 reflections with I > 2σ(I) |
| Radiation source: Nonius FR590 sealed tube generator | Rint = 0.055 |
| horizontally mounted graphite crystal | θmax = 25.0°, θmin = 2.1° |
| Detector resolution: 9 pixels mm-1 | h = −8→8 |
| ω scans with κ offsets | k = −13→13 |
| 12846 measured reflections | l = −14→14 |
| 3338 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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0746P)2 + 0.3813P] where P = (Fo2 + 2Fc2)/3 |
| 3338 reflections | (Δ/σ)max < 0.001 |
| 248 parameters | Δρmax = 0.27 e Å−3 |
| 0 restraints | Δρmin = −0.24 e Å−3 |
| C25H22N2 | γ = 97.920 (2)° |
| Mr = 350.45 | V = 958.36 (7) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.5687 (3) Å | Mo Kα radiation |
| b = 11.3610 (5) Å | µ = 0.07 mm−1 |
| c = 12.1481 (5) Å | T = 160 K |
| α = 111.318 (2)° | 0.28 × 0.28 × 0.18 mm |
| β = 92.757 (2)° |
| Nonius KappaCCD area-detector diffractometer | 2742 reflections with I > 2σ(I) |
| 12846 measured reflections | Rint = 0.055 |
| 3338 independent reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.144 | Δρmax = 0.27 e Å−3 |
| S = 1.05 | Δρmin = −0.24 e Å−3 |
| 3338 reflections | Absolute structure: ? |
| 248 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Experimental. Solvent used: ethanol Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.483 (2) Frames collected: 193 Seconds exposure per frame: 38 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0 |
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 | ||
| N1 | 0.2897 (2) | 0.28665 (14) | 0.85699 (12) | 0.0234 (5) | |
| N43 | 0.2792 (2) | −0.07061 (15) | 1.11208 (13) | 0.0337 (5) | |
| C2 | 0.3019 (2) | 0.16655 (15) | 0.75950 (14) | 0.0221 (5) | |
| C3 | 0.1698 (2) | 0.05895 (16) | 0.77310 (15) | 0.0245 (5) | |
| C4 | 0.2102 (2) | 0.04948 (16) | 0.89088 (15) | 0.0247 (5) | |
| C5 | 0.2147 (3) | 0.17506 (16) | 0.99182 (15) | 0.0259 (5) | |
| C6 | 0.3418 (2) | 0.28366 (16) | 0.97355 (14) | 0.0228 (5) | |
| C21 | 0.2547 (2) | 0.17135 (16) | 0.63899 (15) | 0.0231 (5) | |
| C22 | 0.1527 (3) | 0.25663 (17) | 0.62196 (16) | 0.0305 (6) | |
| C23 | 0.1094 (3) | 0.25267 (18) | 0.50784 (17) | 0.0351 (6) | |
| C24 | 0.1656 (3) | 0.16411 (19) | 0.41083 (16) | 0.0334 (6) | |
| C25 | 0.2624 (3) | 0.07576 (19) | 0.42646 (16) | 0.0326 (6) | |
| C26 | 0.3064 (3) | 0.08000 (18) | 0.53961 (15) | 0.0289 (6) | |
| C41 | 0.2409 (2) | −0.05984 (16) | 0.90312 (14) | 0.0224 (5) | |
| C42 | 0.2639 (2) | −0.06391 (16) | 1.02001 (15) | 0.0229 (5) | |
| C61 | 0.3303 (2) | 0.40939 (15) | 1.07285 (15) | 0.0229 (5) | |
| C62 | 0.4168 (3) | 0.43681 (17) | 1.18522 (16) | 0.0294 (6) | |
| C63 | 0.4012 (3) | 0.54702 (18) | 1.27961 (16) | 0.0332 (6) | |
| C64 | 0.3011 (3) | 0.63333 (18) | 1.26372 (17) | 0.0339 (6) | |
| C65 | 0.2169 (3) | 0.60898 (18) | 1.15273 (17) | 0.0353 (6) | |
| C66 | 0.2303 (3) | 0.49737 (17) | 1.05758 (17) | 0.0297 (6) | |
| C411 | 0.2472 (2) | −0.18250 (16) | 0.80123 (14) | 0.0219 (5) | |
| C412 | 0.3720 (2) | −0.18561 (17) | 0.72031 (15) | 0.0262 (5) | |
| C413 | 0.3729 (3) | −0.29637 (17) | 0.62162 (15) | 0.0282 (6) | |
| C414 | 0.2500 (3) | −0.40591 (17) | 0.60354 (16) | 0.0280 (5) | |
| C415 | 0.1280 (3) | −0.40399 (17) | 0.68462 (16) | 0.0292 (6) | |
| C416 | 0.1269 (3) | −0.29380 (16) | 0.78340 (16) | 0.0268 (6) | |
| H1 | 0.369 (3) | 0.349 (2) | 0.8489 (18) | 0.032 (5)* | |
| H2 | 0.42655 | 0.14747 | 0.76422 | 0.0265* | |
| H3A | 0.04586 | 0.07614 | 0.76593 | 0.0294* | |
| H3B | 0.17785 | −0.02350 | 0.70878 | 0.0294* | |
| H5A | 0.25571 | 0.16749 | 1.06722 | 0.0310* | |
| H5B | 0.09216 | 0.19647 | 0.99775 | 0.0310* | |
| H6 | 0.46768 | 0.26643 | 0.97639 | 0.0273* | |
| H22 | 0.11217 | 0.31797 | 0.68822 | 0.0366* | |
| H23 | 0.04009 | 0.31198 | 0.49694 | 0.0421* | |
| H24 | 0.13807 | 0.16362 | 0.33352 | 0.0401* | |
| H25 | 0.29848 | 0.01237 | 0.35966 | 0.0391* | |
| H26 | 0.37339 | 0.01920 | 0.54979 | 0.0346* | |
| H62 | 0.48774 | 0.37882 | 1.19713 | 0.0353* | |
| H63 | 0.45969 | 0.56346 | 1.35593 | 0.0399* | |
| H64 | 0.29037 | 0.70903 | 1.32881 | 0.0407* | |
| H65 | 0.14914 | 0.66877 | 1.14112 | 0.0424* | |
| H66 | 0.17080 | 0.48112 | 0.98158 | 0.0356* | |
| H412 | 0.45739 | −0.11123 | 0.73267 | 0.0314* | |
| H413 | 0.45778 | −0.29715 | 0.56637 | 0.0338* | |
| H414 | 0.24992 | −0.48166 | 0.53582 | 0.0336* | |
| H415 | 0.04390 | −0.47891 | 0.67264 | 0.0351* | |
| H416 | 0.04356 | −0.29416 | 0.83935 | 0.0322* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0313 (9) | 0.0161 (8) | 0.0203 (8) | 0.0036 (6) | 0.0011 (6) | 0.0044 (6) |
| N43 | 0.0441 (10) | 0.0307 (9) | 0.0234 (9) | 0.0011 (7) | 0.0014 (7) | 0.0088 (7) |
| C2 | 0.0261 (9) | 0.0177 (9) | 0.0196 (9) | 0.0061 (7) | 0.0003 (7) | 0.0031 (7) |
| C3 | 0.0293 (10) | 0.0179 (9) | 0.0223 (9) | 0.0030 (7) | −0.0005 (7) | 0.0036 (7) |
| C4 | 0.0291 (10) | 0.0202 (9) | 0.0214 (9) | 0.0004 (7) | 0.0026 (7) | 0.0053 (7) |
| C5 | 0.0338 (10) | 0.0213 (9) | 0.0200 (9) | 0.0040 (7) | 0.0045 (7) | 0.0047 (7) |
| C6 | 0.0271 (9) | 0.0194 (9) | 0.0193 (9) | 0.0058 (7) | 0.0022 (7) | 0.0037 (7) |
| C21 | 0.0265 (9) | 0.0182 (9) | 0.0227 (9) | 0.0010 (7) | 0.0001 (7) | 0.0069 (7) |
| C22 | 0.0407 (11) | 0.0204 (9) | 0.0279 (10) | 0.0066 (8) | −0.0028 (8) | 0.0064 (8) |
| C23 | 0.0438 (12) | 0.0251 (10) | 0.0355 (11) | 0.0032 (8) | −0.0125 (9) | 0.0133 (9) |
| C24 | 0.0385 (11) | 0.0355 (11) | 0.0243 (10) | −0.0091 (9) | −0.0092 (8) | 0.0158 (9) |
| C25 | 0.0358 (11) | 0.0370 (11) | 0.0217 (9) | 0.0019 (8) | 0.0029 (8) | 0.0087 (8) |
| C26 | 0.0329 (10) | 0.0312 (10) | 0.0240 (9) | 0.0099 (8) | 0.0053 (8) | 0.0102 (8) |
| C41 | 0.0272 (9) | 0.0183 (9) | 0.0191 (8) | 0.0010 (7) | 0.0028 (7) | 0.0051 (7) |
| C42 | 0.0269 (9) | 0.0172 (9) | 0.0208 (9) | 0.0005 (7) | 0.0028 (7) | 0.0038 (7) |
| C61 | 0.0257 (9) | 0.0161 (9) | 0.0231 (9) | 0.0010 (7) | 0.0028 (7) | 0.0039 (7) |
| C62 | 0.0361 (11) | 0.0243 (10) | 0.0248 (9) | 0.0077 (8) | 0.0007 (8) | 0.0049 (8) |
| C63 | 0.0380 (11) | 0.0312 (10) | 0.0220 (9) | 0.0036 (8) | 0.0011 (8) | 0.0011 (8) |
| C64 | 0.0356 (11) | 0.0223 (10) | 0.0305 (10) | 0.0025 (8) | 0.0063 (8) | −0.0052 (8) |
| C65 | 0.0367 (11) | 0.0238 (10) | 0.0399 (12) | 0.0121 (8) | 0.0017 (9) | 0.0032 (8) |
| C66 | 0.0321 (10) | 0.0230 (9) | 0.0288 (10) | 0.0065 (8) | −0.0021 (8) | 0.0037 (8) |
| C411 | 0.0288 (10) | 0.0173 (9) | 0.0183 (8) | 0.0039 (7) | 0.0007 (7) | 0.0053 (7) |
| C412 | 0.0310 (10) | 0.0220 (9) | 0.0215 (9) | −0.0007 (7) | 0.0017 (7) | 0.0054 (7) |
| C413 | 0.0334 (10) | 0.0284 (10) | 0.0199 (9) | 0.0050 (8) | 0.0060 (7) | 0.0055 (7) |
| C414 | 0.0363 (10) | 0.0199 (9) | 0.0232 (9) | 0.0084 (8) | −0.0015 (8) | 0.0019 (7) |
| C415 | 0.0332 (10) | 0.0166 (9) | 0.0348 (10) | −0.0001 (7) | 0.0002 (8) | 0.0079 (8) |
| C416 | 0.0312 (10) | 0.0211 (9) | 0.0288 (10) | 0.0052 (7) | 0.0079 (8) | 0.0092 (8) |
| N1—C2 | 1.464 (2) | C3—H3A | 0.9900 |
| N1—C6 | 1.465 (2) | C3—H3B | 0.9900 |
| N43—C42 | 1.150 (2) | C5—H5B | 0.9900 |
| N1—H1 | 0.90 (2) | C5—H5A | 0.9900 |
| C2—C3 | 1.532 (3) | C6—H6 | 1.0000 |
| C2—C21 | 1.512 (2) | C22—H22 | 0.9500 |
| C3—C4 | 1.494 (2) | C23—H23 | 0.9500 |
| C4—C5 | 1.500 (3) | C24—H24 | 0.9500 |
| C4—C41 | 1.352 (3) | C25—H25 | 0.9500 |
| C5—C6 | 1.546 (3) | C26—H26 | 0.9500 |
| C6—C61 | 1.515 (2) | C62—H62 | 0.9500 |
| C21—C22 | 1.384 (3) | C63—H63 | 0.9500 |
| C21—C26 | 1.391 (3) | C64—H64 | 0.9500 |
| C22—C23 | 1.392 (3) | C65—H65 | 0.9500 |
| C23—C24 | 1.373 (3) | C66—H66 | 0.9500 |
| C24—C25 | 1.381 (3) | C411—C416 | 1.393 (3) |
| C25—C26 | 1.381 (3) | C411—C412 | 1.390 (2) |
| C41—C411 | 1.499 (2) | C412—C413 | 1.388 (3) |
| C41—C42 | 1.441 (2) | C413—C414 | 1.387 (3) |
| C61—C62 | 1.392 (3) | C414—C415 | 1.379 (3) |
| C61—C66 | 1.392 (3) | C415—C416 | 1.385 (3) |
| C62—C63 | 1.381 (3) | C412—H412 | 0.9500 |
| C63—C64 | 1.379 (3) | C413—H413 | 0.9500 |
| C64—C65 | 1.378 (3) | C414—H414 | 0.9500 |
| C65—C66 | 1.391 (3) | C415—H415 | 0.9500 |
| C2—H2 | 1.0000 | C416—H416 | 0.9500 |
| N1···H22 | 2.5600 | H3A···C25v | 3.0500 |
| N1···H66 | 2.5000 | H3B···C26 | 2.8600 |
| N43···H25i | 2.8000 | H3B···C411 | 2.5500 |
| N43···H3Aii | 2.9400 | H3B···C412 | 2.5500 |
| N43···H412iii | 2.7300 | H3B···H412 | 2.5100 |
| C2···C64iv | 3.598 (3) | H3B···C24v | 2.8700 |
| C3···C412 | 3.232 (3) | H3B···H24v | 2.6000 |
| C3···C24v | 3.380 (3) | H5A···C42 | 2.4900 |
| C24···C3v | 3.380 (3) | H5A···C62 | 2.9200 |
| C64···C2iv | 3.598 (3) | H5B···C42ii | 2.8600 |
| C3···H412 | 3.0500 | H5B···H416ii | 2.2600 |
| C3···H24v | 3.0300 | H6···H2 | 2.4200 |
| C4···H412 | 3.0400 | H6···H62 | 2.5000 |
| C5···H416ii | 2.9900 | H22···N1 | 2.5600 |
| C22···H1 | 2.89 (2) | H22···H1 | 2.5800 |
| C22···H415vi | 3.0800 | H22···H415vi | 2.5000 |
| C23···H414vi | 2.9500 | H23···H414vi | 2.5200 |
| C24···H3Bv | 2.8700 | H23···H415vi | 2.5500 |
| C24···H413vii | 2.9900 | H23···C414v | 2.9600 |
| C24···H3Av | 2.9700 | H23···C415v | 3.0600 |
| C25···H3Av | 3.0500 | H24···C3v | 3.0300 |
| C25···H413vii | 3.0300 | H24···H3Bv | 2.6000 |
| C25···H412vii | 3.0200 | H25···N43viii | 2.8000 |
| C26···H3B | 2.8600 | H25···H412vii | 2.5500 |
| C26···H26vii | 2.9100 | H26···H2 | 2.4600 |
| C42···H416 | 2.9500 | H26···C26vii | 2.9100 |
| C42···H5Bii | 2.8600 | H26···H26vii | 2.3200 |
| C42···H5A | 2.4900 | H62···H6 | 2.5000 |
| C62···H1iv | 2.90 (2) | H62···C412iii | 3.0200 |
| C62···H5A | 2.9200 | H62···C413iii | 2.9000 |
| C63···H1iv | 2.81 (2) | H62···C414iii | 2.9500 |
| C64···H1iv | 2.92 (2) | H63···H413ix | 2.4700 |
| C66···H1 | 2.83 (2) | H66···N1 | 2.5000 |
| C412···C3 | 3.232 (3) | H66···H1 | 2.4900 |
| C411···H3B | 2.5500 | H412···C3 | 3.0500 |
| C412···H3B | 2.5500 | H412···C4 | 3.0400 |
| C412···H62iii | 3.0200 | H412···H3B | 2.5100 |
| C413···H62iii | 2.9000 | H412···N43iii | 2.7300 |
| C414···H23v | 2.9600 | H412···C25vii | 3.0200 |
| C414···H62iii | 2.9500 | H412···H25vii | 2.5500 |
| C415···H23v | 3.0600 | H413···H63x | 2.4700 |
| H1···C22 | 2.89 (2) | H413···C24vii | 2.9900 |
| H1···C66 | 2.83 (2) | H413···C25vii | 3.0300 |
| H1···H22 | 2.5800 | H414···C23xi | 2.9500 |
| H1···H66 | 2.4900 | H414···H23xi | 2.5200 |
| H1···C62iv | 2.90 (2) | H415···C22xi | 3.0800 |
| H1···C63iv | 2.81 (2) | H415···H22xi | 2.5000 |
| H1···C64iv | 2.92 (2) | H415···H23xi | 2.5500 |
| H2···H6 | 2.4200 | H416···C42 | 2.9500 |
| H2···H26 | 2.4600 | H416···C5ii | 2.9900 |
| H3A···N43ii | 2.9400 | H416···H5Bii | 2.2600 |
| H3A···C24v | 2.9700 | ||
| C2—N1—C6 | 112.35 (14) | C6—C5—H5A | 109.00 |
| C2—N1—H1 | 107.7 (14) | C6—C5—H5B | 109.00 |
| C6—N1—H1 | 106.2 (13) | H5A—C5—H5B | 108.00 |
| N1—C2—C3 | 108.33 (13) | C61—C6—H6 | 109.00 |
| C3—C2—C21 | 108.25 (13) | N1—C6—H6 | 109.00 |
| N1—C2—C21 | 112.35 (15) | C5—C6—H6 | 109.00 |
| C2—C3—C4 | 110.66 (14) | C21—C22—H22 | 120.00 |
| C3—C4—C5 | 111.94 (16) | C23—C22—H22 | 120.00 |
| C3—C4—C41 | 123.22 (16) | C24—C23—H23 | 120.00 |
| C5—C4—C41 | 124.83 (16) | C22—C23—H23 | 120.00 |
| C4—C5—C6 | 111.10 (15) | C25—C24—H24 | 120.00 |
| C5—C6—C61 | 108.78 (13) | C23—C24—H24 | 120.00 |
| N1—C6—C61 | 111.40 (15) | C26—C25—H25 | 120.00 |
| N1—C6—C5 | 109.03 (14) | C24—C25—H25 | 120.00 |
| C2—C21—C26 | 118.25 (16) | C21—C26—H26 | 119.00 |
| C22—C21—C26 | 118.37 (17) | C25—C26—H26 | 119.00 |
| C2—C21—C22 | 123.24 (15) | C63—C62—H62 | 119.00 |
| C21—C22—C23 | 120.08 (18) | C61—C62—H62 | 119.00 |
| C22—C23—C24 | 120.8 (2) | C62—C63—H63 | 120.00 |
| C23—C24—C25 | 119.54 (18) | C64—C63—H63 | 120.00 |
| C24—C25—C26 | 119.69 (18) | C65—C64—H64 | 120.00 |
| C21—C26—C25 | 121.4 (2) | C63—C64—H64 | 120.00 |
| C4—C41—C411 | 124.24 (15) | C64—C65—H65 | 120.00 |
| C4—C41—C42 | 119.75 (16) | C66—C65—H65 | 120.00 |
| C42—C41—C411 | 115.97 (16) | C65—C66—H66 | 120.00 |
| N43—C42—C41 | 178.0 (2) | C61—C66—H66 | 120.00 |
| C6—C61—C62 | 119.30 (16) | C41—C411—C412 | 119.85 (16) |
| C62—C61—C66 | 118.17 (17) | C41—C411—C416 | 121.41 (15) |
| C6—C61—C66 | 122.48 (15) | C412—C411—C416 | 118.71 (17) |
| C61—C62—C63 | 121.02 (19) | C411—C412—C413 | 120.62 (18) |
| C62—C63—C64 | 120.37 (18) | C412—C413—C414 | 120.12 (18) |
| C63—C64—C65 | 119.49 (19) | C413—C414—C415 | 119.49 (18) |
| C64—C65—C66 | 120.4 (2) | C414—C415—C416 | 120.60 (19) |
| C61—C66—C65 | 120.51 (18) | C411—C416—C415 | 120.43 (18) |
| N1—C2—H2 | 109.00 | C411—C412—H412 | 120.00 |
| C3—C2—H2 | 109.00 | C413—C412—H412 | 120.00 |
| C21—C2—H2 | 109.00 | C412—C413—H413 | 120.00 |
| C4—C3—H3A | 109.00 | C414—C413—H413 | 120.00 |
| C2—C3—H3A | 110.00 | C413—C414—H414 | 120.00 |
| C2—C3—H3B | 110.00 | C415—C414—H414 | 120.00 |
| C4—C3—H3B | 110.00 | C414—C415—H415 | 120.00 |
| H3A—C3—H3B | 108.00 | C416—C415—H415 | 120.00 |
| C4—C5—H5A | 109.00 | C411—C416—H416 | 120.00 |
| C4—C5—H5B | 109.00 | C415—C416—H416 | 120.00 |
| C6—N1—C2—C3 | 62.57 (17) | C2—C21—C26—C25 | 177.69 (19) |
| C6—N1—C2—C21 | −177.90 (13) | C22—C21—C26—C25 | 1.9 (3) |
| C2—N1—C6—C5 | −60.63 (18) | C21—C22—C23—C24 | 0.5 (3) |
| C2—N1—C6—C61 | 179.31 (13) | C22—C23—C24—C25 | 1.7 (3) |
| N1—C2—C3—C4 | −58.01 (17) | C23—C24—C25—C26 | −2.0 (3) |
| C21—C2—C3—C4 | 179.91 (13) | C24—C25—C26—C21 | 0.3 (3) |
| N1—C2—C21—C22 | −21.6 (2) | C4—C41—C411—C412 | 59.5 (2) |
| N1—C2—C21—C26 | 162.77 (16) | C4—C41—C411—C416 | −118.7 (2) |
| C3—C2—C21—C22 | 98.0 (2) | C42—C41—C411—C412 | −122.58 (17) |
| C3—C2—C21—C26 | −77.65 (19) | C42—C41—C411—C416 | 59.2 (2) |
| C2—C3—C4—C5 | 54.50 (19) | C6—C61—C62—C63 | −176.33 (18) |
| C2—C3—C4—C41 | −124.73 (17) | C66—C61—C62—C63 | 1.2 (3) |
| C3—C4—C5—C6 | −52.5 (2) | C6—C61—C66—C65 | 177.04 (18) |
| C41—C4—C5—C6 | 126.76 (17) | C62—C61—C66—C65 | −0.4 (3) |
| C3—C4—C41—C42 | −174.76 (14) | C61—C62—C63—C64 | −0.9 (3) |
| C3—C4—C41—C411 | 3.1 (3) | C62—C63—C64—C65 | −0.2 (3) |
| C5—C4—C41—C42 | 6.1 (3) | C63—C64—C65—C66 | 0.9 (3) |
| C5—C4—C41—C411 | −176.04 (16) | C64—C65—C66—C61 | −0.6 (3) |
| C4—C5—C6—N1 | 54.1 (2) | C41—C411—C412—C413 | −176.23 (17) |
| C4—C5—C6—C61 | 175.76 (14) | C416—C411—C412—C413 | 2.0 (3) |
| N1—C6—C61—C62 | −163.58 (16) | C41—C411—C416—C415 | 176.03 (18) |
| N1—C6—C61—C66 | 19.0 (2) | C412—C411—C416—C415 | −2.2 (3) |
| C5—C6—C61—C62 | 76.2 (2) | C411—C412—C413—C414 | −0.8 (3) |
| C5—C6—C61—C66 | −101.3 (2) | C412—C413—C414—C415 | −0.4 (3) |
| C2—C21—C22—C23 | −177.83 (18) | C413—C414—C415—C416 | 0.2 (3) |
| C26—C21—C22—C23 | −2.2 (3) | C414—C415—C416—C411 | 1.1 (3) |
| Symmetry codes: (i) x, y, z+1; (ii) −x, −y, −z+2; (iii) −x+1, −y, −z+2; (iv) −x+1, −y+1, −z+2; (v) −x, −y, −z+1; (vi) x, y+1, z; (vii) −x+1, −y, −z+1; (viii) x, y, z−1; (ix) x, y+1, z+1; (x) x, y−1, z−1; (xi) x, y−1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C22—H22···N1 | 0.95 | 2.56 | 2.873 (2) | 100 |
| C66—H66···N1 | 0.95 | 2.50 | 2.834 (2) | 101 |
| N1—H1···Cgiv | 0.90 (2) | 2.68 (2) | 3.537 (2) | 159.4 (2) |
| C62—H62···Cgiii | 0.95 | 2.74 | 3.639 | 159 |
| Symmetry codes: (iv) −x+1, −y+1, −z+2; (iii) −x+1, −y, −z+2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C22—H22···N1 | 0.95 | 2.56 | 2.873 (2) | 100 |
| C66—H66···N1 | 0.95 | 2.50 | 2.834 (2) | 101 |
| N1—H1···Cgi | 0.90 (2) | 2.68 (2) | 3.537 (2) | 159.4 (2) |
| C62—H62···Cgii | 0.95 | 2.74 | 3.639 | 159 |
| Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y, −z+2. |
The data collection was carried out by Dr A. Linden of the Institute of Organic Chemistry at the University of Zurich; his help is gratefully acknowledged by AT.
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In the title compound, (I), (Fig. 1), piperidine ring adopts a chair conformation. Two phenyl rings attached to the piperidine ring in positions 2 and 6 have equatorial orientations and make a dihedral angle of 17.9 (1)°. The phenyl-acetonitrile group at position 4 has a bisectional orientation. Molecules are linked by C22—H22···N1, C66—H66···N1 intramolecular and intermolecular hydrogen bonds: N1—H1···π (1 - x, 1 - y, 2 - z) involving the phenyl ring at position 6 and C62—H62···π (1 - x, -y, 2 - z) involving the phenyl ring at C41.