1-Benzoyl-c-3,t-3-dimethyl-r-2,c-6-diphenyl-piperidin-4-one.

In the title compound, C(26)H(25)NO(2), the piperidine ring adopts a distorted boat conformation. The three phenyl rings form dihedral angles of 67.58 (8), 59.82 (8) and 86.41 (8)° with the best plane through the piperidine ring. The crystal packing is governed by inter-molecular C-H⋯O inter-actions.

Related literature

For the biological activity of piperidine derivatives, see: Dimmock et al. (2001 ▶); Perumal et al. (2001 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C26H25NO2

M = 383.47

Monoclinic,

a = 10.8540 (9) Å

b = 17.8050 (17) Å

c = 10.8853 (10) Å

β = 94.987 (3)°

V = 2095.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.977, T max = 0.985

27356 measured reflections

6189 independent reflections

3897 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.152

S = 0.98

6189 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028037/bt2990sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028037/bt2990Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H25NO2	F(000) = 816
Mr = 383.47	Dx = 1.215 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5746 reflections
a = 10.8540 (9) Å	θ = 1.9–30.4°
b = 17.8050 (17) Å	µ = 0.08 mm−1
c = 10.8853 (10) Å	T = 293 K
β = 94.987 (3)°	Block, colorless
V = 2095.7 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII area-detector diffractometer	6189 independent reflections
Radiation source: fine-focus sealed tube	3897 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω and φ scans	θmax = 30.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→13
Tmin = 0.977, Tmax = 0.985	k = −25→25
27356 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0728P)2 + 0.3353P] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.011
6189 reflections	Δρmax = 0.24 e Å−3
265 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0078 (16)

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
O1	0.14493 (11)	0.19520 (7)	0.50443 (9)	0.0560 (3)
O2	0.41301 (12)	0.16165 (9)	1.02065 (10)	0.0722 (4)
N1	0.17515 (10)	0.16380 (6)	0.70591 (9)	0.0338 (2)
C2	0.12064 (12)	0.15019 (8)	0.82403 (11)	0.0361 (3)
H2	0.0881	0.1980	0.8520	0.043*
C3	0.21997 (14)	0.12271 (9)	0.92293 (12)	0.0466 (4)
H3A	0.1886	0.1294	1.0030	0.056*
H3B	0.2313	0.0692	0.9113	0.056*
C4	0.34508 (15)	0.15986 (10)	0.92630 (13)	0.0493 (4)
C5	0.38114 (14)	0.19299 (9)	0.80660 (13)	0.0446 (3)
C6	0.30890 (12)	0.15316 (7)	0.69712 (11)	0.0362 (3)
H6	0.3282	0.1809	0.6235	0.043*
C7	0.10627 (13)	0.19291 (8)	0.60735 (11)	0.0373 (3)
C8	−0.01836 (13)	0.22524 (8)	0.62390 (11)	0.0376 (3)
C9	−0.12156 (16)	0.19732 (9)	0.55574 (16)	0.0543 (4)
H9	−0.1149	0.1550	0.5067	0.065*
C10	−0.23461 (17)	0.23218 (11)	0.5604 (2)	0.0681 (5)
H10	−0.3040	0.2125	0.5155	0.082*
C11	−0.24602 (16)	0.29517 (10)	0.62980 (18)	0.0600 (4)
H11	−0.3223	0.3187	0.6312	0.072*
C12	−0.14437 (17)	0.32334 (10)	0.69727 (17)	0.0588 (4)
H12	−0.1516	0.3664	0.7445	0.071*
C13	−0.03124 (15)	0.28842 (9)	0.69574 (15)	0.0507 (4)
H13	0.0370	0.3075	0.7433	0.061*
C14	0.01468 (13)	0.09444 (8)	0.80976 (12)	0.0385 (3)
C15	0.01631 (15)	0.03311 (8)	0.73135 (15)	0.0485 (4)
H15	0.0832	0.0259	0.6848	0.058*
C16	−0.08083 (17)	−0.01740 (10)	0.72184 (18)	0.0608 (5)
H16	−0.0791	−0.0582	0.6688	0.073*
C17	−0.18017 (18)	−0.00735 (12)	0.7908 (2)	0.0699 (5)
H17	−0.2455	−0.0413	0.7844	0.084*
C18	−0.18221 (18)	0.05259 (13)	0.8683 (2)	0.0724 (6)
H18	−0.2490	0.0592	0.9152	0.087*
C19	−0.08585 (15)	0.10376 (10)	0.87796 (15)	0.0561 (4)
H19	−0.0888	0.1447	0.9307	0.067*
C20	0.34155 (16)	0.27631 (9)	0.80821 (15)	0.0539 (4)
H20A	0.2550	0.2794	0.8196	0.081*
H20B	0.3569	0.2995	0.7314	0.081*
H20C	0.3882	0.3018	0.8747	0.081*
C21	0.52053 (15)	0.19025 (12)	0.79462 (18)	0.0646 (5)
H21A	0.5634	0.2149	0.8642	0.097*
H21B	0.5386	0.2153	0.7202	0.097*
H21C	0.5470	0.1389	0.7920	0.097*
C22	0.34321 (13)	0.07146 (8)	0.67344 (13)	0.0397 (3)
C23	0.40686 (15)	0.02446 (10)	0.75922 (15)	0.0532 (4)
H23	0.4300	0.0424	0.8381	0.064*
C24	0.43630 (17)	−0.04821 (10)	0.72953 (19)	0.0638 (5)
H24	0.4789	−0.0787	0.7882	0.077*
C25	0.40313 (18)	−0.07557 (10)	0.6143 (2)	0.0700 (5)
H25	0.4234	−0.1246	0.5943	0.084*
C26	0.33977 (17)	−0.03070 (10)	0.52792 (18)	0.0627 (5)
H26	0.3162	−0.0495	0.4497	0.075*
C27	0.31101 (14)	0.04226 (9)	0.55720 (14)	0.0475 (4)
H27	0.2691	0.0724	0.4976	0.057*

	U11	U22	U33	U12	U13	U23
O1	0.0589 (7)	0.0747 (8)	0.0352 (5)	0.0155 (6)	0.0096 (5)	0.0121 (5)
O2	0.0575 (8)	0.1115 (11)	0.0444 (6)	−0.0127 (7)	−0.0138 (5)	−0.0013 (6)
N1	0.0348 (6)	0.0364 (6)	0.0304 (5)	−0.0024 (4)	0.0035 (4)	0.0021 (4)
C2	0.0398 (7)	0.0379 (7)	0.0308 (6)	−0.0046 (6)	0.0045 (5)	0.0026 (5)
C3	0.0469 (9)	0.0608 (9)	0.0314 (6)	−0.0062 (7)	−0.0002 (6)	0.0079 (6)
C4	0.0465 (9)	0.0623 (10)	0.0377 (7)	−0.0050 (7)	−0.0046 (6)	−0.0025 (6)
C5	0.0382 (8)	0.0535 (8)	0.0418 (7)	−0.0107 (6)	0.0023 (6)	−0.0053 (6)
C6	0.0346 (7)	0.0400 (7)	0.0342 (6)	−0.0031 (5)	0.0044 (5)	0.0009 (5)
C7	0.0424 (8)	0.0365 (7)	0.0329 (6)	−0.0008 (6)	0.0025 (5)	0.0033 (5)
C8	0.0400 (8)	0.0384 (7)	0.0341 (6)	0.0001 (6)	0.0012 (5)	0.0054 (5)
C9	0.0520 (10)	0.0482 (9)	0.0602 (9)	0.0012 (7)	−0.0090 (7)	−0.0065 (7)
C10	0.0455 (10)	0.0635 (11)	0.0914 (13)	−0.0029 (8)	−0.0171 (9)	−0.0044 (10)
C11	0.0421 (10)	0.0613 (11)	0.0772 (11)	0.0092 (8)	0.0096 (8)	0.0086 (9)
C12	0.0585 (11)	0.0559 (10)	0.0623 (10)	0.0107 (8)	0.0065 (8)	−0.0072 (8)
C13	0.0465 (9)	0.0514 (9)	0.0530 (8)	0.0019 (7)	−0.0029 (7)	−0.0096 (7)
C14	0.0380 (8)	0.0398 (7)	0.0372 (6)	−0.0028 (6)	−0.0002 (5)	0.0102 (5)
C15	0.0461 (9)	0.0402 (8)	0.0588 (9)	−0.0051 (6)	0.0020 (7)	0.0019 (6)
C16	0.0605 (11)	0.0441 (9)	0.0748 (11)	−0.0121 (8)	−0.0106 (9)	0.0065 (8)
C17	0.0543 (11)	0.0667 (12)	0.0860 (13)	−0.0249 (9)	−0.0094 (9)	0.0264 (10)
C18	0.0478 (11)	0.0892 (15)	0.0825 (13)	−0.0161 (10)	0.0185 (9)	0.0165 (11)
C19	0.0482 (10)	0.0659 (11)	0.0556 (9)	−0.0082 (8)	0.0125 (7)	0.0015 (8)
C20	0.0578 (10)	0.0517 (9)	0.0534 (9)	−0.0181 (8)	0.0115 (7)	−0.0115 (7)
C21	0.0408 (10)	0.0849 (13)	0.0679 (11)	−0.0175 (9)	0.0028 (8)	−0.0122 (9)
C22	0.0322 (7)	0.0419 (7)	0.0450 (7)	−0.0006 (6)	0.0034 (5)	0.0021 (6)
C23	0.0476 (9)	0.0557 (9)	0.0546 (9)	0.0042 (7)	−0.0047 (7)	0.0055 (7)
C24	0.0506 (10)	0.0528 (10)	0.0855 (13)	0.0092 (8)	−0.0085 (9)	0.0137 (9)
C25	0.0571 (12)	0.0432 (9)	0.1068 (15)	0.0095 (8)	−0.0094 (10)	−0.0086 (10)
C26	0.0609 (11)	0.0520 (10)	0.0728 (11)	0.0076 (8)	−0.0074 (9)	−0.0174 (8)
C27	0.0454 (9)	0.0468 (8)	0.0493 (8)	0.0055 (7)	−0.0021 (6)	−0.0041 (6)

O1—C7	1.2307 (16)	C14—C19	1.382 (2)
O2—C4	1.2115 (17)	C14—C15	1.387 (2)
N1—C7	1.3561 (16)	C15—C16	1.383 (2)
N1—C6	1.4754 (17)	C15—H15	0.9300
N1—C2	1.4813 (15)	C16—C17	1.378 (3)
C2—C14	1.5170 (19)	C16—H16	0.9300
C2—C3	1.5359 (19)	C17—C18	1.362 (3)
C2—H2	0.9800	C17—H17	0.9300
C3—C4	1.508 (2)	C18—C19	1.384 (3)
C3—H3A	0.9700	C18—H18	0.9300
C3—H3B	0.9700	C19—H19	0.9300
C4—C5	1.513 (2)	C20—H20A	0.9600
C5—C21	1.531 (2)	C20—H20B	0.9600
C5—C6	1.5412 (19)	C20—H20C	0.9600
C5—C20	1.545 (2)	C21—H21A	0.9600
C6—C22	1.529 (2)	C21—H21B	0.9600
C6—H6	0.9800	C21—H21C	0.9600
C7—C8	1.495 (2)	C22—C27	1.384 (2)
C8—C9	1.381 (2)	C22—C23	1.392 (2)
C8—C13	1.384 (2)	C23—C24	1.378 (2)
C9—C10	1.380 (3)	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.364 (3)
C10—C11	1.364 (3)	C24—H24	0.9300
C10—H10	0.9300	C25—C26	1.372 (3)
C11—C12	1.367 (3)	C25—H25	0.9300
C11—H11	0.9300	C26—C27	1.380 (2)
C12—C13	1.378 (2)	C26—H26	0.9300
C12—H12	0.9300	C27—H27	0.9300
C13—H13	0.9300
C7—N1—C6	118.40 (10)	C8—C13—H13	119.7
C7—N1—C2	120.99 (11)	C19—C14—C15	118.55 (14)
C6—N1—C2	120.31 (10)	C19—C14—C2	119.56 (13)
N1—C2—C14	112.00 (10)	C15—C14—C2	121.88 (13)
N1—C2—C3	110.59 (11)	C16—C15—C14	120.51 (16)
C14—C2—C3	110.06 (11)	C16—C15—H15	119.7
N1—C2—H2	108.0	C14—C15—H15	119.7
C14—C2—H2	108.0	C17—C16—C15	120.16 (18)
C3—C2—H2	108.0	C17—C16—H16	119.9
C4—C3—C2	116.94 (12)	C15—C16—H16	119.9
C4—C3—H3A	108.1	C18—C17—C16	119.66 (17)
C2—C3—H3A	108.1	C18—C17—H17	120.2
C4—C3—H3B	108.1	C16—C17—H17	120.2
C2—C3—H3B	108.1	C17—C18—C19	120.68 (18)
H3A—C3—H3B	107.3	C17—C18—H18	119.7
O2—C4—C3	120.83 (14)	C19—C18—H18	119.7
O2—C4—C5	122.41 (15)	C14—C19—C18	120.43 (17)
C3—C4—C5	116.74 (12)	C14—C19—H19	119.8
C4—C5—C21	113.12 (14)	C18—C19—H19	119.8
C4—C5—C6	109.53 (12)	C5—C20—H20A	109.5
C21—C5—C6	111.08 (12)	C5—C20—H20B	109.5
C4—C5—C20	105.76 (12)	H20A—C20—H20B	109.5
C21—C5—C20	108.03 (13)	C5—C20—H20C	109.5
C6—C5—C20	109.10 (12)	H20A—C20—H20C	109.5
N1—C6—C22	112.86 (11)	H20B—C20—H20C	109.5
N1—C6—C5	109.16 (10)	C5—C21—H21A	109.5
C22—C6—C5	116.95 (12)	C5—C21—H21B	109.5
N1—C6—H6	105.6	H21A—C21—H21B	109.5
C22—C6—H6	105.6	C5—C21—H21C	109.5
C5—C6—H6	105.6	H21A—C21—H21C	109.5
O1—C7—N1	121.65 (13)	H21B—C21—H21C	109.5
O1—C7—C8	118.71 (12)	C27—C22—C23	117.29 (14)
N1—C7—C8	119.61 (11)	C27—C22—C6	117.74 (12)
C9—C8—C13	118.61 (14)	C23—C22—C6	124.95 (13)
C9—C8—C7	119.78 (13)	C24—C23—C22	121.26 (16)
C13—C8—C7	121.19 (13)	C24—C23—H23	119.4
C10—C9—C8	120.05 (16)	C22—C23—H23	119.4
C10—C9—H9	120.0	C25—C24—C23	120.19 (16)
C8—C9—H9	120.0	C25—C24—H24	119.9
C11—C10—C9	120.93 (17)	C23—C24—H24	119.9
C11—C10—H10	119.5	C24—C25—C26	119.90 (17)
C9—C10—H10	119.5	C24—C25—H25	120.0
C10—C11—C12	119.45 (16)	C26—C25—H25	120.0
C10—C11—H11	120.3	C25—C26—C27	119.99 (17)
C12—C11—H11	120.3	C25—C26—H26	120.0
C11—C12—C13	120.44 (16)	C27—C26—H26	120.0
C11—C12—H12	119.8	C26—C27—C22	121.36 (15)
C13—C12—H12	119.8	C26—C27—H27	119.3
C12—C13—C8	120.50 (15)	C22—C27—H27	119.3
C12—C13—H13	119.7
C7—N1—C2—C14	61.05 (16)	C13—C8—C9—C10	−0.2 (2)
C6—N1—C2—C14	−125.24 (12)	C7—C8—C9—C10	−172.85 (15)
C7—N1—C2—C3	−175.79 (12)	C8—C9—C10—C11	1.3 (3)
C6—N1—C2—C3	−2.08 (16)	C9—C10—C11—C12	−1.1 (3)
N1—C2—C3—C4	40.28 (18)	C10—C11—C12—C13	−0.2 (3)
C14—C2—C3—C4	164.56 (13)	C11—C12—C13—C8	1.3 (3)
C2—C3—C4—O2	154.70 (16)	C9—C8—C13—C12	−1.1 (2)
C2—C3—C4—C5	−26.3 (2)	C7—C8—C13—C12	171.44 (14)
O2—C4—C5—C21	30.2 (2)	N1—C2—C14—C19	−144.35 (13)
C3—C4—C5—C21	−148.72 (15)	C3—C2—C14—C19	92.20 (16)
O2—C4—C5—C6	154.74 (16)	N1—C2—C14—C15	36.78 (18)
C3—C4—C5—C6	−24.22 (19)	C3—C2—C14—C15	−86.67 (15)
O2—C4—C5—C20	−87.8 (2)	C19—C14—C15—C16	0.1 (2)
C3—C4—C5—C20	93.23 (16)	C2—C14—C15—C16	178.96 (13)
C7—N1—C6—C22	−102.18 (13)	C14—C15—C16—C17	−0.3 (2)
C2—N1—C6—C22	83.95 (14)	C15—C16—C17—C18	0.0 (3)
C7—N1—C6—C5	125.98 (13)	C16—C17—C18—C19	0.4 (3)
C2—N1—C6—C5	−47.89 (15)	C15—C14—C19—C18	0.3 (2)
C4—C5—C6—N1	59.99 (15)	C2—C14—C19—C18	−178.58 (16)
C21—C5—C6—N1	−174.33 (13)	C17—C18—C19—C14	−0.6 (3)
C20—C5—C6—N1	−55.34 (14)	N1—C6—C22—C27	72.51 (15)
C4—C5—C6—C22	−69.65 (16)	C5—C6—C22—C27	−159.62 (13)
C21—C5—C6—C22	56.03 (17)	N1—C6—C22—C23	−108.93 (15)
C20—C5—C6—C22	175.02 (11)	C5—C6—C22—C23	18.9 (2)
C6—N1—C7—O1	16.05 (19)	C27—C22—C23—C24	−0.1 (2)
C2—N1—C7—O1	−170.12 (13)	C6—C22—C23—C24	−178.70 (15)
C6—N1—C7—C8	−162.10 (11)	C22—C23—C24—C25	0.0 (3)
C2—N1—C7—C8	11.73 (18)	C23—C24—C25—C26	−0.3 (3)
O1—C7—C8—C9	59.09 (19)	C24—C25—C26—C27	0.8 (3)
N1—C7—C8—C9	−122.69 (15)	C25—C26—C27—C22	−1.0 (3)
O1—C7—C8—C13	−113.39 (16)	C23—C22—C27—C26	0.6 (2)
N1—C7—C8—C13	64.83 (18)	C6—C22—C27—C26	179.29 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.98	2.29	2.7346 (17)	106
C2—H2···O1i	0.98	2.56	3.3784 (17)	141
C20—H20A···O1i	0.96	2.47	3.1885 (19)	132
C20—H20B···O2ii	0.96	2.52	3.470 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.98	2.29	2.7346 (17)	106
C2—H2⋯O1i	0.98	2.56	3.3784 (17)	141
C20—H20A⋯O1i	0.96	2.47	3.1885 (19)	132
C20—H20B⋯O2ii	0.96	2.52	3.470 (2)	170

Symmetry codes: (i) ; (ii) .