In the title compound, C
17H
19N, the piperidine ring adopts a chair conformation. The phenyl rings substituted at the 2- and 6-positions of the piperidine ring subtend dihedral angles of 81.04 (7) and 81.10 (7)° with the best plane of the piperidine ring. The crystal packing features C—H

π interactions.
Supporting information
CCDC reference: 963452
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.125
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ? Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -0.233
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 11
Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? Do !
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00900 Deg.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K
PLAT793_ALERT_4_G The Model has Chirality at C2 (Verify) .... S
PLAT793_ALERT_4_G The Model has Chirality at C6 (Verify) .... R
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 84
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
7 ALERT level G = General information/check it is not something unexpected
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
A mixture of piperidin-4-one (10 mM) and 80% hydrazine hydrate (3.1 ml)
in diethylene glycol (100 ml) was heated on a steam bath for 2 hrs (Ponnuswamy
et al., 2002). Potassium hydroxide pellets (2.8 g) were added to
the
mixture and the contents were allowed to reflux vigorously on a heating mantle
for another 2 hrs and the reaction mixture was cooled. The product formed was
filtered and recrystallized from ethanol.
All H atoms were found in a difference map. Nevertheless, those bonded
to C
were positioned geometrically (C–H = 0.93–0.98 Å) and
allowed to ride on their parent atoms, with Uiso(H) =
1.2Ueq(C). The H atom bonded to N was freely refined.
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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) and PLATON (Spek, 2009).
r-2,
c-6-Diphenylpiperidine
top
Crystal data top
C17H19N | Z = 2 |
Mr = 237.33 | F(000) = 256 |
Triclinic, P1 | Dx = 1.136 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.6450 (9) Å | Cell parameters from 2113 reflections |
b = 11.2255 (17) Å | θ = 1.8–26.6° |
c = 11.5281 (17) Å | µ = 0.07 mm−1 |
α = 73.911 (9)° | T = 293 K |
β = 89.898 (9)° | Block, white |
γ = 81.466 (9)° | 0.21 × 0.19 × 0.18 mm |
V = 693.53 (18) Å3 | |
Data collection top
Bruker SMART APEXII CCD diffractometer | 2813 independent reflections |
Radiation source: fine-focus sealed tube | 2113 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω and ϕ scans | θmax = 26.6°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −7→7 |
Tmin = 0.986, Tmax = 0.988 | k = −13→14 |
9781 measured reflections | l = −14→14 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0582P)2 + 0.0755P] where P = (Fo2 + 2Fc2)/3 |
2813 reflections | (Δ/σ)max < 0.001 |
167 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Crystal data top
C17H19N | γ = 81.466 (9)° |
Mr = 237.33 | V = 693.53 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.6450 (9) Å | Mo Kα radiation |
b = 11.2255 (17) Å | µ = 0.07 mm−1 |
c = 11.5281 (17) Å | T = 293 K |
α = 73.911 (9)° | 0.21 × 0.19 × 0.18 mm |
β = 89.898 (9)° | |
Data collection top
Bruker SMART APEXII CCD diffractometer | 2813 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2113 reflections with I > 2σ(I) |
Tmin = 0.986, Tmax = 0.988 | Rint = 0.032 |
9781 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.11 e Å−3 |
2813 reflections | Δρmin = −0.20 e Å−3 |
167 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 | Uiso*/Ueq | |
C2 | 0.3110 (2) | 0.28559 (11) | 0.14071 (11) | 0.0526 (3) | |
H2 | 0.4718 | 0.2820 | 0.1084 | 0.063* | |
C3 | 0.1318 (3) | 0.28661 (13) | 0.04187 (13) | 0.0649 (4) | |
H3A | −0.0288 | 0.2927 | 0.0720 | 0.078* | |
H3B | 0.1375 | 0.3595 | −0.0264 | 0.078* | |
C4 | 0.1868 (3) | 0.16823 (14) | 0.00071 (13) | 0.0762 (4) | |
H4A | 0.3376 | 0.1680 | −0.0398 | 0.091* | |
H4B | 0.0619 | 0.1672 | −0.0565 | 0.091* | |
C5 | 0.2026 (3) | 0.05172 (13) | 0.10787 (13) | 0.0680 (4) | |
H5A | 0.2539 | −0.0222 | 0.0809 | 0.082* | |
H5B | 0.0452 | 0.0454 | 0.1407 | 0.082* | |
C6 | 0.3782 (2) | 0.05592 (11) | 0.20619 (12) | 0.0547 (3) | |
H6 | 0.5379 | 0.0580 | 0.1730 | 0.066* | |
C7 | 0.3915 (2) | −0.05597 (11) | 0.31576 (12) | 0.0525 (3) | |
C8 | 0.5902 (3) | −0.14804 (13) | 0.34202 (13) | 0.0643 (4) | |
H8 | 0.7197 | −0.1406 | 0.2919 | 0.077* | |
C9 | 0.5997 (3) | −0.25123 (14) | 0.44165 (15) | 0.0737 (4) | |
H9 | 0.7353 | −0.3123 | 0.4580 | 0.088* | |
C10 | 0.4108 (3) | −0.26438 (14) | 0.51663 (13) | 0.0699 (4) | |
H10 | 0.4176 | −0.3341 | 0.5835 | 0.084* | |
C11 | 0.2118 (3) | −0.17362 (14) | 0.49196 (15) | 0.0747 (4) | |
H11 | 0.0829 | −0.1816 | 0.5425 | 0.090* | |
C12 | 0.2023 (3) | −0.07085 (13) | 0.39271 (14) | 0.0685 (4) | |
H12 | 0.0662 | −0.0101 | 0.3769 | 0.082* | |
C13 | 0.2607 (2) | 0.39961 (11) | 0.18678 (11) | 0.0501 (3) | |
C14 | 0.0632 (3) | 0.41659 (13) | 0.25525 (13) | 0.0618 (4) | |
H14 | −0.0411 | 0.3577 | 0.2714 | 0.074* | |
C15 | 0.0190 (3) | 0.51912 (14) | 0.29970 (15) | 0.0735 (4) | |
H15 | −0.1140 | 0.5289 | 0.3459 | 0.088* | |
C16 | 0.1715 (3) | 0.60761 (14) | 0.27597 (15) | 0.0754 (4) | |
H16 | 0.1422 | 0.6768 | 0.3063 | 0.090* | |
C17 | 0.3659 (3) | 0.59283 (14) | 0.20757 (15) | 0.0734 (4) | |
H17 | 0.4680 | 0.6527 | 0.1908 | 0.088* | |
C18 | 0.4119 (3) | 0.48965 (12) | 0.16320 (12) | 0.0604 (4) | |
H18 | 0.5453 | 0.4804 | 0.1172 | 0.072* | |
N1 | 0.30501 (19) | 0.17179 (9) | 0.24060 (10) | 0.0527 (3) | |
H1 | 0.397 (3) | 0.1732 (13) | 0.3027 (14) | 0.066 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0521 (7) | 0.0509 (7) | 0.0556 (7) | −0.0122 (5) | 0.0034 (6) | −0.0143 (6) |
C3 | 0.0785 (9) | 0.0594 (8) | 0.0559 (8) | −0.0142 (7) | −0.0073 (7) | −0.0128 (6) |
C4 | 0.1052 (12) | 0.0700 (9) | 0.0583 (8) | −0.0204 (8) | −0.0091 (8) | −0.0225 (7) |
C5 | 0.0859 (10) | 0.0597 (8) | 0.0655 (9) | −0.0183 (7) | −0.0016 (7) | −0.0255 (7) |
C6 | 0.0543 (7) | 0.0504 (7) | 0.0614 (8) | −0.0093 (5) | 0.0064 (6) | −0.0183 (6) |
C7 | 0.0547 (7) | 0.0476 (7) | 0.0595 (7) | −0.0083 (5) | 0.0012 (6) | −0.0217 (6) |
C8 | 0.0604 (8) | 0.0652 (9) | 0.0672 (9) | −0.0004 (7) | 0.0016 (7) | −0.0231 (7) |
C9 | 0.0791 (10) | 0.0627 (9) | 0.0734 (10) | 0.0087 (7) | −0.0137 (8) | −0.0192 (8) |
C10 | 0.0935 (11) | 0.0570 (8) | 0.0580 (8) | −0.0140 (8) | −0.0090 (8) | −0.0130 (7) |
C11 | 0.0819 (11) | 0.0673 (9) | 0.0728 (10) | −0.0147 (8) | 0.0162 (8) | −0.0145 (8) |
C12 | 0.0646 (9) | 0.0564 (8) | 0.0788 (10) | −0.0017 (6) | 0.0114 (7) | −0.0134 (7) |
C13 | 0.0523 (7) | 0.0469 (7) | 0.0489 (7) | −0.0089 (5) | −0.0042 (5) | −0.0093 (5) |
C14 | 0.0610 (8) | 0.0571 (8) | 0.0674 (8) | −0.0119 (6) | 0.0053 (7) | −0.0160 (7) |
C15 | 0.0747 (10) | 0.0723 (10) | 0.0744 (10) | −0.0002 (8) | 0.0043 (8) | −0.0277 (8) |
C16 | 0.0932 (12) | 0.0606 (9) | 0.0760 (10) | −0.0017 (8) | −0.0151 (9) | −0.0300 (8) |
C17 | 0.0845 (11) | 0.0602 (9) | 0.0810 (10) | −0.0244 (8) | −0.0089 (9) | −0.0215 (8) |
C18 | 0.0621 (8) | 0.0595 (8) | 0.0618 (8) | −0.0179 (6) | −0.0014 (6) | −0.0162 (6) |
N1 | 0.0583 (6) | 0.0468 (6) | 0.0540 (6) | −0.0091 (5) | −0.0049 (5) | −0.0154 (5) |
Geometric parameters (Å, º) top
C2—N1 | 1.4685 (16) | C9—C10 | 1.370 (2) |
C2—C13 | 1.5064 (17) | C9—H9 | 0.9300 |
C2—C3 | 1.5217 (19) | C10—C11 | 1.372 (2) |
C2—H2 | 0.9800 | C10—H10 | 0.9300 |
C3—C4 | 1.5211 (19) | C11—C12 | 1.376 (2) |
C3—H3A | 0.9700 | C11—H11 | 0.9300 |
C3—H3B | 0.9700 | C12—H12 | 0.9300 |
C4—C5 | 1.521 (2) | C13—C14 | 1.3857 (18) |
C4—H4A | 0.9700 | C13—C18 | 1.3881 (17) |
C4—H4B | 0.9700 | C14—C15 | 1.375 (2) |
C5—C6 | 1.522 (2) | C14—H14 | 0.9300 |
C5—H5A | 0.9700 | C15—C16 | 1.380 (2) |
C5—H5B | 0.9700 | C15—H15 | 0.9300 |
C6—N1 | 1.4648 (16) | C16—C17 | 1.367 (2) |
C6—C7 | 1.5072 (18) | C16—H16 | 0.9300 |
C6—H6 | 0.9800 | C17—C18 | 1.382 (2) |
C7—C8 | 1.3789 (19) | C17—H17 | 0.9300 |
C7—C12 | 1.3867 (19) | C18—H18 | 0.9300 |
C8—C9 | 1.381 (2) | N1—H1 | 0.891 (16) |
C8—H8 | 0.9300 | | |
| | | |
N1—C2—C13 | 109.73 (10) | C9—C8—H8 | 119.5 |
N1—C2—C3 | 108.14 (10) | C10—C9—C8 | 120.55 (14) |
C13—C2—C3 | 113.09 (11) | C10—C9—H9 | 119.7 |
N1—C2—H2 | 108.6 | C8—C9—H9 | 119.7 |
C13—C2—H2 | 108.6 | C9—C10—C11 | 119.28 (14) |
C3—C2—H2 | 108.6 | C9—C10—H10 | 120.4 |
C4—C3—C2 | 111.00 (12) | C11—C10—H10 | 120.4 |
C4—C3—H3A | 109.4 | C10—C11—C12 | 120.17 (15) |
C2—C3—H3A | 109.4 | C10—C11—H11 | 119.9 |
C4—C3—H3B | 109.4 | C12—C11—H11 | 119.9 |
C2—C3—H3B | 109.4 | C11—C12—C7 | 121.37 (14) |
H3A—C3—H3B | 108.0 | C11—C12—H12 | 119.3 |
C3—C4—C5 | 110.73 (12) | C7—C12—H12 | 119.3 |
C3—C4—H4A | 109.5 | C14—C13—C18 | 118.18 (12) |
C5—C4—H4A | 109.5 | C14—C13—C2 | 120.72 (11) |
C3—C4—H4B | 109.5 | C18—C13—C2 | 121.09 (12) |
C5—C4—H4B | 109.5 | C15—C14—C13 | 121.03 (13) |
H4A—C4—H4B | 108.1 | C15—C14—H14 | 119.5 |
C4—C5—C6 | 111.35 (11) | C13—C14—H14 | 119.5 |
C4—C5—H5A | 109.4 | C14—C15—C16 | 120.15 (15) |
C6—C5—H5A | 109.4 | C14—C15—H15 | 119.9 |
C4—C5—H5B | 109.4 | C16—C15—H15 | 119.9 |
C6—C5—H5B | 109.4 | C17—C16—C15 | 119.52 (14) |
H5A—C5—H5B | 108.0 | C17—C16—H16 | 120.2 |
N1—C6—C7 | 110.02 (10) | C15—C16—H16 | 120.2 |
N1—C6—C5 | 108.40 (11) | C16—C17—C18 | 120.58 (14) |
C7—C6—C5 | 112.75 (10) | C16—C17—H17 | 119.7 |
N1—C6—H6 | 108.5 | C18—C17—H17 | 119.7 |
C7—C6—H6 | 108.5 | C17—C18—C13 | 120.54 (14) |
C5—C6—H6 | 108.5 | C17—C18—H18 | 119.7 |
C8—C7—C12 | 117.66 (13) | C13—C18—H18 | 119.7 |
C8—C7—C6 | 121.30 (12) | C6—N1—C2 | 113.14 (10) |
C12—C7—C6 | 121.04 (11) | C6—N1—H1 | 110.1 (9) |
C7—C8—C9 | 120.97 (14) | C2—N1—H1 | 109.7 (9) |
C7—C8—H8 | 119.5 | | |
| | | |
N1—C2—C3—C4 | −56.90 (15) | C6—C7—C12—C11 | 179.08 (13) |
C13—C2—C3—C4 | −178.62 (11) | N1—C2—C13—C14 | −50.66 (15) |
C2—C3—C4—C5 | 53.73 (18) | C3—C2—C13—C14 | 70.16 (15) |
C3—C4—C5—C6 | −53.20 (18) | N1—C2—C13—C18 | 128.55 (12) |
C4—C5—C6—N1 | 55.84 (15) | C3—C2—C13—C18 | −110.63 (14) |
C4—C5—C6—C7 | 177.89 (12) | C18—C13—C14—C15 | −0.6 (2) |
N1—C6—C7—C8 | −130.46 (12) | C2—C13—C14—C15 | 178.63 (13) |
C5—C6—C7—C8 | 108.40 (14) | C13—C14—C15—C16 | 0.3 (2) |
N1—C6—C7—C12 | 50.58 (15) | C14—C15—C16—C17 | 0.3 (2) |
C5—C6—C7—C12 | −70.56 (16) | C15—C16—C17—C18 | −0.6 (2) |
C12—C7—C8—C9 | −0.1 (2) | C16—C17—C18—C13 | 0.4 (2) |
C6—C7—C8—C9 | −179.06 (12) | C14—C13—C18—C17 | 0.25 (19) |
C7—C8—C9—C10 | 0.1 (2) | C2—C13—C18—C17 | −178.98 (12) |
C8—C9—C10—C11 | −0.2 (2) | C7—C6—N1—C2 | 174.32 (10) |
C9—C10—C11—C12 | 0.2 (2) | C5—C6—N1—C2 | −61.97 (13) |
C10—C11—C12—C7 | −0.2 (2) | C13—C2—N1—C6 | −173.66 (10) |
C8—C7—C12—C11 | 0.1 (2) | C3—C2—N1—C6 | 62.57 (14) |
Hydrogen-bond geometry (Å, º) topCg1 and Cg2 are the centroids of the C13–C18 and C7–C12 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···Cg1i | 0.97 | 3.00 | 3.719 (2) | 132 |
C10—H10···Cg1ii | 0.93 | 3.01 | 3.760 (2) | 139 |
C16—H16···Cg2iii | 0.93 | 3.03 | 3.799 (2) | 141 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+2, −z+1; (iii) x, y−1, z. |
Hydrogen-bond geometry (Å, º) topCg1 and Cg2 are the centroids of the C13–C18 and C7–C12 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···Cg1i | 0.97 | 3.00 | 3.719 (2) | 131.97 |
C10—H10···Cg1ii | 0.93 | 3.01 | 3.760 (2) | 138.49 |
C16—H16···Cg2iii | 0.93 | 3.03 | 3.799 (2) | 141.22 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+2, −z+1; (iii) x, y−1, z. |
Piperidines are valuable heterocyclic compounds found in natural substances and pharmaceutical products (Rubiralta et al., 1991; Jain et al., 2005; Kubota et al., 1998). Several 2,6-substituted piperidine derivatives were found to be useful as tranquilisers (Boehringer & Söhne GmbH, 1961) and possess a wide range of biological activities such as antiviral, antimalarial, antibacterial and antifungal activities (Aridoss et al., 2009, Mobio et al., 1989). In view of the above importance, the crystallographic study of the title compound has been carried out to establish its molecular structure.
The ORTEP plot of the molecule is shown in Fig. 1. The piperidine ring adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) and asymmetry parameters (Nardelli, 1983): q2=0.0420 (15) Å, q3 = -0.5799 (15) Å, ϕ2 = 190 (2)° and Δs (N1& C4)= 0.75 (12)°. The phenyl rings at 2,6-positions of the piperidine ring occupy equatorial positions. The corresponding torsion angles are [C13—C2—C3—C4] -178.62 (11)° & [C4—C5—C6—C7] 177.89 (12)°, respectively. The dihedral angle between the two phenyl rings is 60.0 (7)°. The phenyl rings [C7—C12 & C13—C18] are twisted away from the best plane of the piperidine moiety by 81.04 (7)° & 81.10 (7)°, respectively. The molecules in the unit cell are connected by C—H ···π interactions (Fig. 2 & Table. 1; Cg1 is the centroid of the ring C13 to C18 and Cg2 is the centroid of the ring C7 to C12).