(E)-3-Isopropyl-1-methyl-2,6-di-phenyl-piperidin-4-one O-nicotinoyl oxime.

In the title compound, C27H29N3O2, the piperidine ring exists in a chair conformation with an equatorial orientation of the phenyl and methyl substituents. The C-C=N bond angles are significantly different [119.1 (2) and 127.2 (2)°]. The phenyl rings are inclined to one another by 44.90 (14)°, and by 80.85 (13) and 79.62 (12)° to the mean plane of the piperidine ring. The terminal pyridine ring is inclined to the piperidine ring mean plane by 74.79 (15)°. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For the synthesis and biological activity of piperidin-4-one derivatives, see, for example: Parthiban et al. (2009 ▶); Narayanan et al. (2012 ▶). For the crystal structures of very similar compounds, see: Vinuchakkaravarthy et al. (2013a ▶,b ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C27H29N3O2

M = 427.53

Orthorhombic,

a = 12.7717 (6) Å

b = 16.2765 (7) Å

c = 11.4109 (9) Å

V = 2372.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.491, T max = 0.746

11654 measured reflections

5117 independent reflections

2975 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.132

S = 1.03

5117 reflections

292 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814007363/su2680sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007363/su2680Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007363/su2680Isup3.cml

CCDC reference: 995062

Additional supporting information: crystallographic information; 3D view; checkCIF report

C27H29N3O2	F(000) = 912
Mr = 427.53	Dx = 1.197 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5117 reflections
a = 12.7717 (6) Å	θ = 2.0–28.3°
b = 16.2765 (7) Å	µ = 0.08 mm−1
c = 11.4109 (9) Å	T = 293 K
V = 2372.1 (2) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.20 mm

Bruker SMART APEXII CCD diffractometer	5117 independent reflections
Radiation source: fine-focus sealed tube	2975 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω amd φ scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→14
Tmin = 0.491, Tmax = 0.746	k = −21→16
11654 measured reflections	l = −12→15

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0556P)2 + 0.1257P] where P = (Fo2 + 2Fc2)/3
5117 reflections	(Δ/σ)max < 0.001
292 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.14 e Å−3

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
C1	0.20093 (18)	0.54079 (15)	0.4090 (2)	0.0521 (6)
H1	0.1920	0.5854	0.3523	0.063*
C2	0.29009 (17)	0.48375 (15)	0.3647 (2)	0.0540 (6)
H2	0.2969	0.4405	0.4240	0.065*
C3	0.39055 (18)	0.53079 (15)	0.3689 (2)	0.0512 (6)
C4	0.41492 (19)	0.56519 (17)	0.4867 (2)	0.0563 (6)
H4A	0.4796	0.5963	0.4832	0.068*
H4B	0.4241	0.5208	0.5425	0.068*
C5	0.32572 (18)	0.62083 (15)	0.5264 (2)	0.0509 (6)
H5	0.3216	0.6677	0.4727	0.061*
C6	0.09879 (17)	0.49393 (16)	0.4170 (2)	0.0547 (6)
C7	0.0836 (2)	0.43621 (18)	0.5037 (2)	0.0648 (7)
H7	0.1361	0.4267	0.5585	0.078*
C8	−0.0087 (2)	0.39242 (19)	0.5100 (3)	0.0775 (9)
H8	−0.0178	0.3534	0.5688	0.093*
C9	−0.0869 (2)	0.4060 (2)	0.4306 (4)	0.0844 (10)
H9	−0.1492	0.3765	0.4355	0.101*
C10	−0.0733 (2)	0.4626 (2)	0.3444 (3)	0.0864 (10)
H10	−0.1259	0.4713	0.2894	0.104*
C11	0.0187 (2)	0.5076 (2)	0.3384 (3)	0.0729 (8)
H11	0.0265	0.5475	0.2807	0.087*
C12	0.2629 (2)	0.43909 (18)	0.2496 (3)	0.0656 (7)
H12	0.1952	0.4125	0.2628	0.079*
C13	0.3406 (2)	0.3698 (2)	0.2243 (4)	0.0901 (11)
H13A	0.3168	0.3386	0.1580	0.135*
H13B	0.3456	0.3345	0.2914	0.135*
H13C	0.4082	0.3928	0.2075	0.135*
C14	0.2487 (2)	0.4935 (2)	0.1429 (3)	0.0937 (10)
H14A	0.3158	0.5127	0.1167	0.141*
H14B	0.2054	0.5396	0.1630	0.141*
H14C	0.2159	0.4625	0.0814	0.141*
C15	0.5761 (2)	0.62544 (18)	0.2066 (3)	0.0616 (7)
C16	0.6794 (2)	0.66287 (17)	0.2345 (3)	0.0655 (8)
C17	0.7231 (3)	0.7185 (2)	0.1568 (4)	0.0922 (10)
H17	0.6883	0.7329	0.0883	0.111*
C18	0.8190 (4)	0.7520 (2)	0.1830 (4)	0.1076 (14)
H18	0.8497	0.7906	0.1338	0.129*
C19	0.8680 (3)	0.7271 (3)	0.2831 (5)	0.1080 (14)
H19	0.9336	0.7492	0.2989	0.130*
N3	0.8297 (2)	0.67423 (19)	0.3587 (3)	0.1028 (10)
C21	0.7358 (3)	0.64310 (19)	0.3324 (3)	0.0793 (9)
H21	0.7067	0.6054	0.3843	0.095*
C22	0.35138 (17)	0.65246 (16)	0.6471 (2)	0.0532 (6)
C23	0.3903 (2)	0.73080 (17)	0.6616 (3)	0.0643 (7)
H23	0.3944	0.7659	0.5975	0.077*
C24	0.4232 (2)	0.7578 (2)	0.7699 (3)	0.0749 (8)
H24	0.4491	0.8109	0.7781	0.090*
C25	0.4180 (2)	0.7075 (2)	0.8649 (3)	0.0792 (9)
H25	0.4408	0.7259	0.9377	0.095*
C26	0.3788 (2)	0.6292 (2)	0.8524 (3)	0.0748 (8)
H26	0.3743	0.5948	0.9173	0.090*
C27	0.34641 (19)	0.60174 (18)	0.7443 (2)	0.0615 (7)
H27	0.3209	0.5485	0.7364	0.074*
C28	0.1417 (2)	0.63578 (19)	0.5558 (3)	0.0726 (8)
H28A	0.1567	0.6592	0.6311	0.109*
H28B	0.0758	0.6075	0.5588	0.109*
H28C	0.1384	0.6787	0.4982	0.109*
N1	0.22489 (14)	0.57741 (12)	0.52408 (17)	0.0523 (5)
N2	0.44194 (16)	0.54136 (15)	0.27484 (19)	0.0606 (6)
O1	0.53751 (13)	0.58708 (12)	0.29990 (16)	0.0637 (5)
O2	0.53326 (18)	0.63179 (16)	0.1144 (2)	0.0924 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0479 (13)	0.0507 (15)	0.0576 (15)	0.0025 (11)	−0.0069 (11)	−0.0015 (11)
C2	0.0462 (13)	0.0553 (15)	0.0607 (15)	0.0013 (11)	0.0002 (11)	−0.0026 (13)
C3	0.0453 (12)	0.0525 (15)	0.0556 (14)	0.0039 (10)	−0.0006 (11)	−0.0039 (12)
C4	0.0454 (13)	0.0680 (18)	0.0554 (14)	−0.0058 (12)	−0.0026 (11)	−0.0015 (12)
C5	0.0535 (14)	0.0458 (14)	0.0536 (13)	−0.0060 (11)	−0.0033 (11)	0.0019 (11)
C6	0.0440 (14)	0.0579 (16)	0.0623 (15)	0.0045 (11)	−0.0007 (11)	−0.0118 (13)
C7	0.0552 (15)	0.073 (2)	0.0660 (18)	−0.0035 (14)	0.0046 (12)	−0.0131 (15)
C8	0.0678 (19)	0.075 (2)	0.090 (2)	−0.0116 (16)	0.0204 (17)	−0.0194 (17)
C9	0.0539 (18)	0.084 (3)	0.115 (3)	−0.0101 (16)	0.0090 (19)	−0.034 (2)
C10	0.0494 (16)	0.096 (3)	0.113 (3)	0.0037 (17)	−0.0174 (17)	−0.031 (2)
C11	0.0577 (16)	0.075 (2)	0.086 (2)	0.0084 (15)	−0.0131 (14)	−0.0123 (16)
C12	0.0518 (15)	0.0688 (19)	0.0762 (18)	−0.0028 (13)	−0.0025 (13)	−0.0221 (15)
C13	0.069 (2)	0.081 (2)	0.120 (3)	0.0027 (16)	0.0055 (18)	−0.042 (2)
C14	0.088 (2)	0.125 (3)	0.0678 (19)	0.015 (2)	−0.0179 (16)	−0.019 (2)
C15	0.0657 (16)	0.0581 (18)	0.0611 (17)	0.0092 (14)	0.0157 (14)	0.0019 (13)
C16	0.0666 (17)	0.0517 (17)	0.0781 (19)	−0.0034 (13)	0.0257 (16)	−0.0086 (14)
C17	0.098 (3)	0.081 (2)	0.097 (2)	−0.005 (2)	0.035 (2)	0.0062 (19)
C18	0.119 (3)	0.086 (3)	0.118 (4)	−0.035 (2)	0.053 (3)	−0.003 (2)
C19	0.096 (3)	0.093 (3)	0.135 (4)	−0.039 (2)	0.039 (3)	−0.032 (3)
N3	0.0872 (19)	0.095 (2)	0.126 (3)	−0.0257 (17)	−0.0013 (19)	−0.019 (2)
C21	0.080 (2)	0.071 (2)	0.087 (2)	−0.0186 (17)	0.0047 (17)	−0.0029 (17)
C22	0.0451 (13)	0.0557 (16)	0.0589 (15)	0.0005 (11)	−0.0003 (11)	−0.0035 (12)
C23	0.0682 (16)	0.0553 (17)	0.0694 (17)	−0.0019 (14)	−0.0091 (13)	−0.0013 (13)
C24	0.0781 (19)	0.064 (2)	0.083 (2)	−0.0002 (15)	−0.0138 (15)	−0.0186 (17)
C25	0.083 (2)	0.092 (3)	0.0635 (18)	0.0030 (17)	−0.0075 (16)	−0.0227 (18)
C26	0.0719 (17)	0.097 (3)	0.0553 (16)	0.0007 (16)	0.0053 (14)	0.0051 (16)
C27	0.0590 (16)	0.0676 (19)	0.0580 (16)	−0.0072 (13)	0.0066 (12)	0.0030 (14)
C28	0.0561 (15)	0.0680 (19)	0.094 (2)	0.0086 (14)	−0.0002 (14)	−0.0209 (15)
N1	0.0442 (10)	0.0519 (13)	0.0608 (12)	0.0003 (9)	−0.0013 (9)	−0.0066 (10)
N2	0.0501 (12)	0.0657 (15)	0.0660 (14)	−0.0036 (10)	−0.0007 (10)	−0.0088 (11)
O1	0.0567 (10)	0.0744 (13)	0.0601 (11)	−0.0105 (9)	0.0055 (8)	−0.0032 (9)
O2	0.0921 (15)	0.1099 (19)	0.0752 (16)	−0.0005 (13)	−0.0031 (12)	0.0219 (13)

C1—N1	1.474 (3)	C14—H14A	0.9600
C1—C6	1.514 (3)	C14—H14B	0.9600
C1—C2	1.554 (3)	C14—H14C	0.9600
C1—H1	0.9800	C15—O2	1.189 (3)
C2—C3	1.495 (3)	C15—O1	1.329 (3)
C2—C12	1.541 (4)	C15—C16	1.488 (4)
C2—H2	0.9800	C16—C21	1.367 (4)
C3—N2	1.270 (3)	C16—C17	1.385 (4)
C3—C4	1.489 (3)	C17—C18	1.372 (5)
C4—C5	1.524 (4)	C17—H17	0.9300
C4—H4A	0.9700	C18—C19	1.363 (6)
C4—H4B	0.9700	C18—H18	0.9300
C5—N1	1.469 (3)	C19—N3	1.313 (5)
C5—C22	1.507 (3)	C19—H19	0.9300
C5—H5	0.9800	N3—C21	1.336 (4)
C6—C11	1.378 (4)	C21—H21	0.9300
C6—C7	1.378 (4)	C22—C23	1.378 (4)
C7—C8	1.379 (4)	C22—C27	1.383 (4)
C7—H7	0.9300	C23—C24	1.377 (4)
C8—C9	1.366 (5)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.360 (4)
C9—C10	1.360 (5)	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.377 (4)
C10—C11	1.387 (4)	C25—H25	0.9300
C10—H10	0.9300	C26—C27	1.377 (4)
C11—H11	0.9300	C26—H26	0.9300
C12—C14	1.516 (5)	C27—H27	0.9300
C12—C13	1.529 (4)	C28—N1	1.471 (3)
C12—H12	0.9800	C28—H28A	0.9600
C13—H13A	0.9600	C28—H28B	0.9600
C13—H13B	0.9600	C28—H28C	0.9600
C13—H13C	0.9600	N2—O1	1.458 (3)
N1—C1—C6	109.24 (19)	H13B—C13—H13C	109.5
N1—C1—C2	112.30 (18)	C12—C14—H14A	109.5
C6—C1—C2	110.48 (19)	C12—C14—H14B	109.5
N1—C1—H1	108.2	H14A—C14—H14B	109.5
C6—C1—H1	108.2	C12—C14—H14C	109.5
C2—C1—H1	108.2	H14A—C14—H14C	109.5
C3—C2—C12	117.5 (2)	H14B—C14—H14C	109.5
C3—C2—C1	108.21 (19)	O2—C15—O1	125.3 (3)
C12—C2—C1	113.24 (19)	O2—C15—C16	124.2 (3)
C3—C2—H2	105.6	O1—C15—C16	110.5 (3)
C12—C2—H2	105.6	C21—C16—C17	117.7 (3)
C1—C2—H2	105.6	C21—C16—C15	123.1 (3)
N2—C3—C4	127.2 (2)	C17—C16—C15	119.2 (3)
N2—C3—C2	119.1 (2)	C18—C17—C16	118.7 (4)
C4—C3—C2	113.6 (2)	C18—C17—H17	120.7
C3—C4—C5	109.6 (2)	C16—C17—H17	120.7
C3—C4—H4A	109.7	C19—C18—C17	118.3 (4)
C5—C4—H4A	109.7	C19—C18—H18	120.9
C3—C4—H4B	109.7	C17—C18—H18	120.9
C5—C4—H4B	109.7	N3—C19—C18	125.0 (4)
H4A—C4—H4B	108.2	N3—C19—H19	117.5
N1—C5—C22	111.80 (19)	C18—C19—H19	117.5
N1—C5—C4	111.34 (19)	C19—N3—C21	115.8 (4)
C22—C5—C4	108.20 (19)	N3—C21—C16	124.5 (3)
N1—C5—H5	108.5	N3—C21—H21	117.7
C22—C5—H5	108.5	C16—C21—H21	117.7
C4—C5—H5	108.5	C23—C22—C27	118.2 (2)
C11—C6—C7	118.2 (2)	C23—C22—C5	120.3 (2)
C11—C6—C1	121.3 (3)	C27—C22—C5	121.2 (2)
C7—C6—C1	120.5 (2)	C24—C23—C22	120.8 (3)
C6—C7—C8	120.7 (3)	C24—C23—H23	119.6
C6—C7—H7	119.7	C22—C23—H23	119.6
C8—C7—H7	119.7	C25—C24—C23	120.6 (3)
C9—C8—C7	120.4 (3)	C25—C24—H24	119.7
C9—C8—H8	119.8	C23—C24—H24	119.7
C7—C8—H8	119.8	C24—C25—C26	119.5 (3)
C10—C9—C8	119.8 (3)	C24—C25—H25	120.2
C10—C9—H9	120.1	C26—C25—H25	120.2
C8—C9—H9	120.1	C27—C26—C25	120.2 (3)
C9—C10—C11	120.1 (3)	C27—C26—H26	119.9
C9—C10—H10	119.9	C25—C26—H26	119.9
C11—C10—H10	119.9	C26—C27—C22	120.7 (3)
C6—C11—C10	120.8 (3)	C26—C27—H27	119.6
C6—C11—H11	119.6	C22—C27—H27	119.6
C10—C11—H11	119.6	N1—C28—H28A	109.5
C14—C12—C13	110.9 (3)	N1—C28—H28B	109.5
C14—C12—C2	115.9 (2)	H28A—C28—H28B	109.5
C13—C12—C2	111.3 (2)	N1—C28—H28C	109.5
C14—C12—H12	106.0	H28A—C28—H28C	109.5
C13—C12—H12	106.0	H28B—C28—H28C	109.5
C2—C12—H12	106.0	C5—N1—C28	108.55 (19)
C12—C13—H13A	109.5	C5—N1—C1	113.11 (18)
C12—C13—H13B	109.5	C28—N1—C1	109.30 (19)
H13A—C13—H13B	109.5	C3—N2—O1	109.64 (19)
C12—C13—H13C	109.5	C15—O1—N2	113.1 (2)
H13A—C13—H13C	109.5
N1—C1—C2—C3	−52.7 (3)	C15—C16—C17—C18	−179.3 (3)
C6—C1—C2—C3	−174.9 (2)	C16—C17—C18—C19	1.8 (5)
N1—C1—C2—C12	175.2 (2)	C17—C18—C19—N3	−1.5 (6)
C6—C1—C2—C12	52.9 (3)	C18—C19—N3—C21	0.7 (6)
C12—C2—C3—N2	9.3 (3)	C19—N3—C21—C16	−0.2 (5)
C1—C2—C3—N2	−120.5 (2)	C17—C16—C21—N3	0.5 (5)
C12—C2—C3—C4	−174.6 (2)	C15—C16—C21—N3	178.5 (3)
C1—C2—C3—C4	55.7 (3)	N1—C5—C22—C23	−135.9 (2)
N2—C3—C4—C5	118.2 (3)	C4—C5—C22—C23	101.1 (3)
C2—C3—C4—C5	−57.6 (3)	N1—C5—C22—C27	50.4 (3)
C3—C4—C5—N1	55.1 (3)	C4—C5—C22—C27	−72.5 (3)
C3—C4—C5—C22	178.3 (2)	C27—C22—C23—C24	−0.1 (4)
N1—C1—C6—C11	128.0 (2)	C5—C22—C23—C24	−173.9 (2)
C2—C1—C6—C11	−108.0 (3)	C22—C23—C24—C25	0.1 (5)
N1—C1—C6—C7	−51.9 (3)	C23—C24—C25—C26	−0.5 (5)
C2—C1—C6—C7	72.1 (3)	C24—C25—C26—C27	0.8 (5)
C11—C6—C7—C8	1.2 (4)	C25—C26—C27—C22	−0.8 (4)
C1—C6—C7—C8	−178.9 (2)	C23—C22—C27—C26	0.4 (4)
C6—C7—C8—C9	−0.4 (4)	C5—C22—C27—C26	174.2 (2)
C7—C8—C9—C10	0.4 (5)	C22—C5—N1—C28	62.5 (3)
C8—C9—C10—C11	−1.2 (5)	C4—C5—N1—C28	−176.4 (2)
C7—C6—C11—C10	−2.0 (4)	C22—C5—N1—C1	−176.0 (2)
C1—C6—C11—C10	178.1 (3)	C4—C5—N1—C1	−54.9 (2)
C9—C10—C11—C6	2.0 (4)	C6—C1—N1—C5	177.12 (19)
C3—C2—C12—C14	−62.2 (3)	C2—C1—N1—C5	54.2 (3)
C1—C2—C12—C14	65.2 (3)	C6—C1—N1—C28	−61.8 (3)
C3—C2—C12—C13	65.7 (3)	C2—C1—N1—C28	175.2 (2)
C1—C2—C12—C13	−167.0 (2)	C4—C3—N2—O1	5.6 (3)
O2—C15—C16—C21	−168.0 (3)	C2—C3—N2—O1	−178.9 (2)
O1—C15—C16—C21	14.4 (4)	O2—C15—O1—N2	8.8 (4)
O2—C15—C16—C17	10.0 (4)	C16—C15—O1—N2	−173.59 (19)
O1—C15—C16—C17	−167.7 (3)	C3—N2—O1—C15	−157.5 (2)
C21—C16—C17—C18	−1.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···Cg1i	0.93	2.87	3.700 (4)	150
C13—H13C···Cg2ii	0.96	2.95	3.620 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of rings C6–C11 and C22–C27, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24⋯Cg1i	0.93	2.87	3.700 (4)	150
C13—H13C⋯Cg2ii	0.96	2.95	3.620 (3)	128

Symmetry codes: (i) ; (ii) .