1-Formyl-r-2,c-6-bis-(4-methoxy-phen-yl)-t-3,t-5-dimethyl-piperidin-4-one.

In the title compound, C(22)H(25)NO(4), the piperidine ring adopts a distorted boat conformation. The methyl groups at the 3 and 5 positions of the piperidine ring are in axial and equatorial orientations, respectively. Both H and O atoms in the aldehyde group are disordered over two positions with occupancies of 0.534 (5) and 0.466 (5). In the crystal, the mol-ecules are linked into a three-dimensional network by C-H⋯O hydrogen bonds.

Related literature

For general background to piperidine derivatives, see: Escolano & Amat (2006 ▶); Wang & Wuorola (1992 ▶); Grishina et al. (1994 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H25NO4

M = 367.43

Monoclinic,

a = 11.0954 (4) Å

b = 14.5407 (3) Å

c = 12.7050 (4) Å

β = 110.977 (1)°

V = 1913.91 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.974, T max = 0.974

24720 measured reflections

5524 independent reflections

3703 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.140

S = 1.05

5524 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 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 I, global. DOI: 10.1107/S1600536809041609/ci2909sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041609/ci2909Isup2.hkl

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

C22H25NO4	F(000) = 784
Mr = 367.43	Dx = 1.275 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5524 reflections
a = 11.0954 (4) Å	θ = 2.1–29.9°
b = 14.5407 (3) Å	µ = 0.09 mm−1
c = 12.7050 (4) Å	T = 293 K
β = 110.977 (1)°	Block, colourless
V = 1913.91 (10) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	5524 independent reflections
Radiation source: fine-focus sealed tube	3703 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω and φ scans	θmax = 29.9°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→12
Tmin = 0.974, Tmax = 0.974	k = −20→19
24720 measured reflections	l = −17→17

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0598P)2 + 0.3189P] where P = (Fo2 + 2Fc2)/3
5524 reflections	(Δ/σ)max = 0.001
256 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.23 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	Occ. (<1)
O1	0.87856 (11)	0.03534 (7)	0.05971 (10)	0.0574 (3)
O2	1.0929 (3)	0.3733 (2)	0.3086 (2)	0.1143 (15)	0.534 (5)
O2'	1.2050 (3)	0.3881 (2)	0.2198 (3)	0.1036 (16)	0.466 (5)
O3	0.92438 (12)	0.33025 (8)	−0.37580 (9)	0.0647 (3)
O4	0.60958 (11)	0.58982 (7)	0.13202 (9)	0.0600 (3)
N1	1.03399 (11)	0.28962 (8)	0.15129 (9)	0.0446 (3)
C2	1.08936 (13)	0.22990 (9)	0.08641 (11)	0.0433 (3)
H2	1.1831	0.2389	0.1177	0.052*
C3	1.06451 (13)	0.13017 (10)	0.10905 (12)	0.0455 (3)
H3	1.0976	0.0906	0.0631	0.055*
C4	0.92172 (13)	0.11238 (9)	0.07622 (11)	0.0408 (3)
C5	0.83662 (12)	0.19522 (9)	0.06811 (11)	0.0397 (3)
H5	0.8182	0.2227	−0.0064	0.048*
C6	0.90568 (13)	0.26797 (9)	0.15605 (10)	0.0402 (3)
H6	0.9198	0.2415	0.2305	0.048*
C7	1.1102 (2)	0.34871 (18)	0.22651 (19)	0.0930 (7)
H7	1.1815	0.3720	0.2133	0.112*	0.534 (5)
H7'	1.0887	0.3619	0.2918	0.112*	0.466 (5)
C8	1.04508 (12)	0.25691 (9)	−0.03708 (11)	0.0405 (3)
C9	1.01446 (16)	0.19282 (10)	−0.12353 (13)	0.0536 (4)
H9	1.0200	0.1305	−0.1062	0.064*
C10	0.97608 (17)	0.21971 (11)	−0.23422 (13)	0.0582 (4)
H10	0.9554	0.1753	−0.2906	0.070*
C11	0.96764 (14)	0.31160 (10)	−0.26313 (12)	0.0472 (3)
C12	1.00016 (15)	0.37652 (10)	−0.17907 (13)	0.0517 (4)
H12	0.9968	0.4387	−0.1968	0.062*
C13	1.03795 (14)	0.34869 (10)	−0.06774 (13)	0.0496 (3)
H13	1.0593	0.3932	−0.0115	0.060*
C14	1.13194 (17)	0.10344 (14)	0.23312 (14)	0.0675 (5)
H14A	1.2219	0.1187	0.2568	0.101*
H14B	1.1227	0.0385	0.2417	0.101*
H14C	1.0934	0.1364	0.2786	0.101*
C15	0.70806 (15)	0.16822 (11)	0.07688 (17)	0.0619 (4)
H15A	0.6531	0.2213	0.0637	0.093*
H15B	0.7224	0.1444	0.1509	0.093*
H15C	0.6675	0.1219	0.0216	0.093*
C16	0.82499 (13)	0.35393 (9)	0.14503 (11)	0.0406 (3)
C17	0.79081 (14)	0.40931 (9)	0.05079 (11)	0.0435 (3)
H17	0.8174	0.3932	−0.0084	0.052*
C18	0.71800 (14)	0.48820 (9)	0.04184 (11)	0.0444 (3)
H18	0.6960	0.5246	−0.0225	0.053*
C19	0.67825 (13)	0.51235 (9)	0.12957 (11)	0.0433 (3)
C20	0.70878 (16)	0.45640 (11)	0.22319 (12)	0.0533 (4)
H20	0.6803	0.4715	0.2815	0.064*
C21	0.78103 (16)	0.37843 (10)	0.23047 (12)	0.0518 (4)
H21	0.8009	0.3413	0.2940	0.062*
C22	0.9119 (2)	0.42401 (13)	−0.40951 (16)	0.0748 (5)
H22A	0.8799	0.4276	−0.4903	0.112*
H22B	0.9946	0.4535	−0.3797	0.112*
H22C	0.8527	0.4543	−0.3813	0.112*
C23	0.58744 (18)	0.65403 (12)	0.04332 (15)	0.0655 (5)
H23A	0.5442	0.7070	0.0578	0.098*
H23B	0.5346	0.6263	−0.0265	0.098*
H23C	0.6685	0.6723	0.0386	0.098*

	U11	U22	U33	U12	U13	U23
O1	0.0733 (7)	0.0333 (5)	0.0769 (7)	−0.0017 (5)	0.0407 (6)	−0.0034 (5)
O2	0.096 (2)	0.140 (3)	0.085 (2)	0.0135 (19)	0.0052 (15)	−0.072 (2)
O2'	0.0510 (18)	0.085 (2)	0.156 (3)	−0.0229 (15)	0.0140 (18)	−0.046 (2)
O3	0.0798 (8)	0.0614 (7)	0.0550 (6)	0.0062 (6)	0.0265 (6)	0.0104 (5)
O4	0.0746 (7)	0.0486 (6)	0.0589 (6)	0.0254 (5)	0.0266 (5)	0.0045 (5)
N1	0.0411 (6)	0.0452 (6)	0.0437 (6)	−0.0008 (5)	0.0105 (5)	−0.0090 (5)
C2	0.0353 (6)	0.0446 (8)	0.0507 (7)	0.0034 (5)	0.0162 (6)	−0.0003 (6)
C3	0.0479 (8)	0.0426 (8)	0.0514 (8)	0.0141 (6)	0.0243 (6)	0.0085 (6)
C4	0.0526 (8)	0.0337 (7)	0.0423 (7)	0.0041 (6)	0.0244 (6)	0.0024 (5)
C5	0.0399 (6)	0.0335 (6)	0.0467 (7)	0.0032 (5)	0.0166 (5)	0.0013 (5)
C6	0.0479 (7)	0.0379 (7)	0.0366 (6)	0.0073 (6)	0.0173 (5)	0.0014 (5)
C7	0.0728 (13)	0.1154 (18)	0.0846 (14)	−0.0275 (13)	0.0205 (11)	−0.0533 (13)
C8	0.0373 (6)	0.0380 (7)	0.0518 (7)	0.0001 (5)	0.0227 (6)	0.0001 (6)
C9	0.0768 (11)	0.0344 (7)	0.0575 (9)	0.0039 (7)	0.0337 (8)	0.0006 (6)
C10	0.0841 (12)	0.0440 (8)	0.0535 (9)	0.0016 (8)	0.0330 (8)	−0.0051 (7)
C11	0.0452 (7)	0.0494 (8)	0.0525 (8)	0.0033 (6)	0.0242 (6)	0.0044 (6)
C12	0.0569 (9)	0.0368 (7)	0.0652 (9)	−0.0021 (6)	0.0264 (7)	0.0065 (7)
C13	0.0550 (8)	0.0379 (7)	0.0588 (8)	−0.0072 (6)	0.0237 (7)	−0.0043 (6)
C14	0.0601 (10)	0.0778 (12)	0.0615 (10)	0.0226 (9)	0.0179 (8)	0.0232 (9)
C15	0.0469 (8)	0.0496 (9)	0.0950 (13)	0.0020 (7)	0.0323 (8)	−0.0004 (8)
C16	0.0500 (7)	0.0346 (7)	0.0385 (6)	0.0058 (5)	0.0175 (5)	−0.0017 (5)
C17	0.0535 (8)	0.0428 (7)	0.0378 (6)	0.0063 (6)	0.0208 (6)	−0.0009 (5)
C18	0.0526 (8)	0.0398 (7)	0.0402 (7)	0.0050 (6)	0.0159 (6)	0.0042 (6)
C19	0.0473 (7)	0.0361 (7)	0.0460 (7)	0.0059 (6)	0.0160 (6)	−0.0032 (5)
C20	0.0732 (10)	0.0496 (9)	0.0462 (8)	0.0149 (7)	0.0324 (7)	0.0006 (6)
C21	0.0746 (10)	0.0454 (8)	0.0412 (7)	0.0165 (7)	0.0280 (7)	0.0066 (6)
C22	0.0856 (13)	0.0710 (12)	0.0707 (11)	0.0147 (10)	0.0316 (10)	0.0259 (9)
C23	0.0765 (11)	0.0466 (9)	0.0673 (10)	0.0210 (8)	0.0183 (9)	0.0075 (8)

O1—C4	1.2067 (16)	C10—C11	1.380 (2)
O2—C7	1.182 (3)	C10—H10	0.93
O2'—C7	1.227 (4)	C11—C12	1.373 (2)
O3—C11	1.3642 (18)	C12—C13	1.384 (2)
O3—C22	1.421 (2)	C12—H12	0.93
O4—C19	1.3665 (16)	C13—H13	0.93
O4—C23	1.416 (2)	C14—H14A	0.96
N1—C7	1.337 (2)	C14—H14B	0.96
N1—C2	1.4743 (17)	C14—H14C	0.96
N1—C6	1.4803 (17)	C15—H15A	0.96
C2—C8	1.5183 (19)	C15—H15B	0.96
C2—C3	1.523 (2)	C15—H15C	0.96
C2—H2	0.98	C16—C17	1.3787 (18)
C3—C4	1.509 (2)	C16—C21	1.3865 (18)
C3—C14	1.533 (2)	C17—C18	1.3840 (19)
C3—H3	0.98	C17—H17	0.93
C4—C5	1.5111 (18)	C18—C19	1.3829 (19)
C5—C15	1.521 (2)	C18—H18	0.93
C5—C6	1.5302 (18)	C19—C20	1.379 (2)
C5—H5	0.98	C20—C21	1.372 (2)
C6—C16	1.5145 (18)	C20—H20	0.93
C6—H6	0.98	C21—H21	0.93
C7—H7	0.93	C22—H22A	0.96
C7—H7'	0.96	C22—H22B	0.96
C8—C13	1.385 (2)	C22—H22C	0.96
C8—C9	1.387 (2)	C23—H23A	0.96
C9—C10	1.372 (2)	C23—H23B	0.96
C9—H9	0.93	C23—H23C	0.96
C11—O3—C22	117.82 (13)	C12—C11—C10	118.99 (14)
C19—O4—C23	117.70 (12)	C11—C12—C13	119.53 (14)
C7—N1—C2	119.66 (14)	C11—C12—H12	120.2
C7—N1—C6	118.59 (14)	C13—C12—H12	120.2
C2—N1—C6	119.80 (10)	C12—C13—C8	122.36 (14)
N1—C2—C8	112.33 (11)	C12—C13—H13	118.8
N1—C2—C3	108.39 (11)	C8—C13—H13	118.8
C8—C2—C3	115.34 (12)	C3—C14—H14A	109.5
N1—C2—H2	106.8	C3—C14—H14B	109.5
C8—C2—H2	106.8	H14A—C14—H14B	109.5
C3—C2—H2	106.8	C3—C14—H14C	109.5
C4—C3—C2	110.75 (11)	H14A—C14—H14C	109.5
C4—C3—C14	108.56 (12)	H14B—C14—H14C	109.5
C2—C3—C14	112.39 (13)	C5—C15—H15A	109.5
C4—C3—H3	108.3	C5—C15—H15B	109.5
C2—C3—H3	108.3	H15A—C15—H15B	109.5
C14—C3—H3	108.3	C5—C15—H15C	109.5
O1—C4—C3	121.28 (12)	H15A—C15—H15C	109.5
O1—C4—C5	121.92 (13)	H15B—C15—H15C	109.5
C3—C4—C5	116.79 (11)	C17—C16—C21	117.74 (12)
C4—C5—C15	111.63 (11)	C17—C16—C6	122.14 (11)
C4—C5—C6	111.35 (11)	C21—C16—C6	120.11 (12)
C15—C5—C6	111.25 (12)	C16—C17—C18	121.77 (12)
C4—C5—H5	107.5	C16—C17—H17	119.1
C15—C5—H5	107.5	C18—C17—H17	119.1
C6—C5—H5	107.5	C19—C18—C17	119.31 (12)
N1—C6—C16	111.47 (11)	C19—C18—H18	120.3
N1—C6—C5	110.78 (10)	C17—C18—H18	120.3
C16—C6—C5	112.22 (10)	O4—C19—C20	115.68 (12)
N1—C6—H6	107.4	O4—C19—C18	124.68 (12)
C16—C6—H6	107.4	C20—C19—C18	119.63 (12)
C5—C6—H6	107.4	C21—C20—C19	120.17 (12)
O2—C7—O2'	109.5 (3)	C21—C20—H20	119.9
O2—C7—N1	124.4 (3)	C19—C20—H20	119.9
O2'—C7—N1	126.1 (3)	C20—C21—C16	121.34 (13)
O2—C7—H7	117.8	C20—C21—H21	119.3
N1—C7—H7	117.8	C16—C21—H21	119.3
O2'—C7—H7'	116.8	O3—C22—H22A	109.5
N1—C7—H7'	117.2	O3—C22—H22B	109.5
C13—C8—C9	116.86 (13)	H22A—C22—H22B	109.5
C13—C8—C2	120.31 (12)	O3—C22—H22C	109.5
C9—C8—C2	122.79 (12)	H22A—C22—H22C	109.5
C10—C9—C8	121.23 (14)	H22B—C22—H22C	109.5
C10—C9—H9	119.4	O4—C23—H23A	109.5
C8—C9—H9	119.4	O4—C23—H23B	109.5
C9—C10—C11	121.01 (14)	H23A—C23—H23B	109.5
C9—C10—H10	119.5	O4—C23—H23C	109.5
C11—C10—H10	119.5	H23A—C23—H23C	109.5
O3—C11—C12	125.11 (13)	H23B—C23—H23C	109.5
O3—C11—C10	115.89 (13)
C7—N1—C2—C8	−109.80 (19)	N1—C2—C8—C9	−140.48 (13)
C6—N1—C2—C8	86.30 (14)	C3—C2—C8—C9	−15.60 (18)
C7—N1—C2—C3	121.58 (18)	C13—C8—C9—C10	−1.5 (2)
C6—N1—C2—C3	−42.33 (16)	C2—C8—C9—C10	−179.28 (14)
N1—C2—C3—C4	58.59 (14)	C8—C9—C10—C11	0.5 (3)
C8—C2—C3—C4	−68.32 (14)	C22—O3—C11—C12	0.1 (2)
N1—C2—C3—C14	−63.02 (15)	C22—O3—C11—C10	178.86 (15)
C8—C2—C3—C14	170.07 (11)	C9—C10—C11—O3	−177.91 (14)
C2—C3—C4—O1	160.79 (13)	C9—C10—C11—C12	0.9 (2)
C14—C3—C4—O1	−75.37 (17)	O3—C11—C12—C13	177.39 (14)
C2—C3—C4—C5	−20.74 (16)	C10—C11—C12—C13	−1.3 (2)
C14—C3—C4—C5	103.09 (14)	C11—C12—C13—C8	0.3 (2)
O1—C4—C5—C15	19.05 (19)	C9—C8—C13—C12	1.1 (2)
C3—C4—C5—C15	−159.40 (12)	C2—C8—C13—C12	178.93 (13)
O1—C4—C5—C6	144.05 (13)	N1—C6—C16—C17	60.77 (17)
C3—C4—C5—C6	−34.40 (15)	C5—C6—C16—C17	−64.16 (17)
C7—N1—C6—C16	57.6 (2)	N1—C6—C16—C21	−120.35 (14)
C2—N1—C6—C16	−138.34 (12)	C5—C6—C16—C21	114.73 (15)
C7—N1—C6—C5	−176.69 (17)	C21—C16—C17—C18	1.7 (2)
C2—N1—C6—C5	−12.62 (16)	C6—C16—C17—C18	−179.42 (13)
C4—C5—C6—N1	51.38 (14)	C16—C17—C18—C19	0.0 (2)
C15—C5—C6—N1	176.60 (11)	C23—O4—C19—C20	173.65 (15)
C4—C5—C6—C16	176.69 (10)	C23—O4—C19—C18	−5.9 (2)
C15—C5—C6—C16	−58.09 (15)	C17—C18—C19—O4	177.91 (13)
C2—N1—C7—O2	−150.5 (3)	C17—C18—C19—C20	−1.7 (2)
C6—N1—C7—O2	13.6 (4)	O4—C19—C20—C21	−177.95 (15)
C2—N1—C7—O2'	32.2 (4)	C18—C19—C20—C21	1.7 (2)
C6—N1—C7—O2'	−163.7 (3)	C19—C20—C21—C16	0.0 (3)
N1—C2—C8—C13	41.78 (17)	C17—C16—C21—C20	−1.7 (2)
C3—C2—C8—C13	166.66 (12)	C6—C16—C21—C20	179.39 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.98	2.48	3.429 (2)	163
C15—H15C···O2ii	0.96	2.53	3.240 (4)	131
C20—H20···O1iii	0.93	2.51	3.432 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.98	2.48	3.429 (2)	163
C15—H15C⋯O2ii	0.96	2.53	3.240 (4)	131
C20—H20⋯O1iii	0.93	2.51	3.432 (2)	171

Symmetry codes: (i) ; (ii) ; (iii) .