r-2,c-6-Bis(2-methoxy-phen-yl)-t-3,t-5-dimethyl-piperidin-4-one acetic acid solvate.

In the title compound, C(21)H(25)NO(3)·C(2)H(4)O(2), the piperidone ring adopts a chair conformation. The two meth-oxy groups are nearly coplanar with the aromatic rings to which they are attached. The dihedral angle between the two aromatic rings is 60.9 (2)°. There are two short intra-molecular N-H⋯O contacts. The crystal packing is stabilized by inter-molecular O-H⋯N and C-H⋯O inter-actions.

Related literature

For related structures see: Aridoss et al. (2008 ▶),(2009 ▶); Gayathri et al. (2008 ▶). For the synthesis of the title compound, see Noller & Baliah (1948 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C21H25NO3·C2H4O2

M = 399.47

Triclinic,

a = 9.3059 (5) Å

b = 10.7052 (8) Å

c = 11.8950 (7) Å

α = 94.432 (3)°

β = 93.341 (2)°

γ = 109.502 (3)°

V = 1109.21 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 292 K

0.25 × 0.23 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.979, T max = 0.983

19986 measured reflections

5528 independent reflections

3271 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.173

S = 1.00

5528 reflections

271 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.26 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017721/bt5268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017721/bt5268Isup2.hkl

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

C21H25NO3·C2H4O2	Z = 2
Mr = 399.47	F(000) = 428
Triclinic, P1	Dx = 1.196 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3059 (5) Å	Cell parameters from 3180 reflections
b = 10.7052 (8) Å	θ = 1.7–28.4°
c = 11.8950 (7) Å	µ = 0.08 mm−1
α = 94.432 (3)°	T = 292 K
β = 93.341 (2)°	Block, colorless
γ = 109.502 (3)°	0.25 × 0.23 × 0.2 mm
V = 1109.21 (12) Å3

Bruker SMART APEXII area-detector diffractometer	5528 independent reflections
Radiation source: fine-focus sealed tube	3271 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω and φ scans	θmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.979, Tmax = 0.983	k = −14→14
19986 measured reflections	l = −15→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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0885P)2 + 0.1246P] where P = (Fo2 + 2Fc2)/3
5528 reflections	(Δ/σ)max = 0.005
271 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O4	0.2740 (2)	0.8721 (2)	0.70402 (14)	0.1087 (6)
C1	0.43491 (17)	0.18195 (15)	0.14948 (13)	0.0541 (4)
H1A	0.5080	0.1344	0.1425	0.065*
C2	0.4178 (2)	0.2350 (2)	0.03418 (14)	0.0678 (5)
H2	0.3463	0.2842	0.0403	0.081*
C3	0.5705 (2)	0.33189 (19)	0.01370 (14)	0.0650 (5)
C4	0.6393 (2)	0.44701 (17)	0.10477 (14)	0.0623 (4)
H4	0.5714	0.4999	0.1081	0.075*
C5	0.64521 (17)	0.38984 (14)	0.21975 (12)	0.0505 (4)
H5	0.7209	0.3445	0.2168	0.061*
C6	0.70122 (19)	0.49821 (14)	0.31787 (13)	0.0533 (4)
C7	0.6116 (2)	0.57269 (15)	0.35615 (14)	0.0589 (4)
C8	0.6675 (3)	0.67106 (17)	0.44625 (16)	0.0746 (5)
H8	0.6069	0.7190	0.4722	0.089*
C9	0.8122 (3)	0.6977 (2)	0.49702 (18)	0.0866 (6)
H9	0.8495	0.7645	0.5569	0.104*
C10	0.9024 (3)	0.6271 (2)	0.46067 (18)	0.0828 (6)
H10	1.0005	0.6458	0.4953	0.099*
C11	0.8457 (2)	0.52775 (17)	0.37193 (16)	0.0659 (5)
H11	0.9067	0.4794	0.3479	0.079*
C12	0.3732 (3)	0.6129 (2)	0.33376 (19)	0.0891 (6)
H12A	0.3540	0.6013	0.4114	0.134*
H12B	0.2781	0.5795	0.2870	0.134*
H12C	0.4220	0.7058	0.3261	0.134*
C13	0.7967 (3)	0.5374 (2)	0.08009 (19)	0.0865 (6)
H13A	0.8662	0.4883	0.0799	0.130*
H13B	0.8335	0.6117	0.1374	0.130*
H13C	0.7897	0.5692	0.0074	0.130*
C14	0.3526 (3)	0.1237 (3)	−0.06128 (18)	0.1039 (8)
H14A	0.3557	0.1612	−0.1322	0.156*
H14B	0.2486	0.0737	−0.0501	0.156*
H14C	0.4124	0.0659	−0.0619	0.156*
C15	0.28810 (18)	0.08293 (16)	0.18040 (14)	0.0569 (4)
C16	0.2765 (2)	−0.04794 (18)	0.18907 (17)	0.0723 (5)
H16	0.3608	−0.0737	0.1765	0.087*
C17	0.1441 (2)	−0.1413 (2)	0.2158 (2)	0.0871 (6)
H17	0.1385	−0.2292	0.2196	0.104*
C18	0.0207 (2)	−0.1035 (2)	0.2366 (2)	0.0838 (6)
H18	−0.0684	−0.1659	0.2560	0.101*
C19	0.0267 (2)	0.0254 (2)	0.22903 (16)	0.0717 (5)
H19	−0.0577	0.0502	0.2433	0.086*
C20	0.15927 (18)	0.11803 (17)	0.20012 (14)	0.0600 (4)
C21	0.0428 (3)	0.2846 (3)	0.1817 (2)	0.0973 (7)
H21A	−0.0251	0.2319	0.1186	0.146*
H21B	0.0704	0.3773	0.1706	0.146*
H21C	−0.0075	0.2686	0.2500	0.146*
N1	0.49978 (14)	0.28941 (12)	0.24234 (10)	0.0474 (3)
O1	0.63714 (19)	0.31782 (17)	−0.06797 (12)	0.0943 (5)
O2	0.47078 (15)	0.54141 (12)	0.29933 (11)	0.0716 (4)
O3	0.17552 (13)	0.24937 (12)	0.19021 (12)	0.0731 (4)
H1	0.4328 (19)	0.3276 (16)	0.2563 (14)	0.057 (4)*
C22	0.2703 (3)	0.9465 (3)	0.5224 (2)	0.0980 (7)
H22A	0.1935	0.9802	0.5490	0.147*
H22B	0.2283	0.8846	0.4562	0.147*
H22C	0.3560	1.0191	0.5037	0.147*
C23	0.32168 (18)	0.87804 (16)	0.61225 (16)	0.0609 (4)
O5	0.42181 (15)	0.82324 (12)	0.58533 (10)	0.0707 (4)
H5A	0.4448	0.7887	0.6396	0.106*

	U11	U22	U33	U12	U13	U23
O4	0.1096 (12)	0.1637 (16)	0.1017 (12)	0.0972 (12)	0.0448 (10)	0.0488 (11)
C1	0.0527 (9)	0.0637 (9)	0.0533 (9)	0.0328 (7)	0.0022 (7)	−0.0067 (7)
C2	0.0644 (11)	0.0993 (13)	0.0521 (10)	0.0474 (10)	0.0012 (8)	−0.0032 (9)
C3	0.0784 (12)	0.0886 (12)	0.0474 (9)	0.0524 (10)	0.0108 (8)	0.0105 (8)
C4	0.0791 (11)	0.0689 (10)	0.0558 (9)	0.0436 (9)	0.0180 (8)	0.0150 (8)
C5	0.0546 (9)	0.0532 (8)	0.0522 (9)	0.0279 (7)	0.0105 (7)	0.0074 (6)
C6	0.0645 (10)	0.0476 (8)	0.0509 (9)	0.0214 (7)	0.0101 (7)	0.0100 (6)
C7	0.0749 (11)	0.0507 (8)	0.0555 (9)	0.0261 (8)	0.0117 (8)	0.0064 (7)
C8	0.1046 (16)	0.0570 (10)	0.0654 (11)	0.0316 (10)	0.0157 (11)	0.0011 (8)
C9	0.1166 (18)	0.0630 (11)	0.0681 (12)	0.0196 (12)	−0.0063 (12)	−0.0067 (9)
C10	0.0855 (14)	0.0684 (12)	0.0818 (13)	0.0133 (10)	−0.0152 (11)	0.0076 (10)
C11	0.0691 (11)	0.0575 (9)	0.0707 (11)	0.0205 (8)	0.0032 (9)	0.0107 (8)
C12	0.1012 (16)	0.0992 (15)	0.0907 (15)	0.0668 (13)	0.0186 (12)	−0.0036 (11)
C13	0.1080 (17)	0.0800 (13)	0.0780 (13)	0.0317 (12)	0.0350 (12)	0.0286 (10)
C14	0.0884 (15)	0.150 (2)	0.0606 (13)	0.0355 (15)	−0.0106 (11)	−0.0285 (13)
C15	0.0508 (9)	0.0637 (9)	0.0575 (9)	0.0255 (7)	−0.0010 (7)	−0.0103 (7)
C16	0.0595 (11)	0.0656 (11)	0.0921 (14)	0.0272 (9)	−0.0021 (9)	−0.0101 (9)
C17	0.0714 (13)	0.0614 (11)	0.1236 (19)	0.0202 (10)	−0.0025 (12)	−0.0002 (11)
C18	0.0596 (11)	0.0755 (13)	0.1040 (16)	0.0105 (9)	0.0009 (10)	−0.0023 (11)
C19	0.0513 (10)	0.0833 (13)	0.0797 (13)	0.0254 (9)	0.0025 (8)	−0.0048 (10)
C20	0.0529 (9)	0.0651 (10)	0.0644 (10)	0.0265 (8)	0.0010 (7)	−0.0066 (8)
C21	0.0762 (13)	0.1153 (17)	0.131 (2)	0.0613 (13)	0.0365 (13)	0.0465 (15)
N1	0.0480 (7)	0.0521 (7)	0.0486 (7)	0.0264 (6)	0.0079 (5)	0.0001 (5)
O1	0.1128 (11)	0.1183 (12)	0.0627 (8)	0.0504 (9)	0.0354 (8)	0.0029 (7)
O2	0.0794 (8)	0.0754 (8)	0.0738 (8)	0.0476 (7)	0.0080 (7)	−0.0074 (6)
O3	0.0597 (7)	0.0747 (8)	0.0979 (10)	0.0392 (6)	0.0169 (6)	0.0049 (7)
C22	0.0881 (15)	0.1015 (16)	0.1127 (18)	0.0350 (12)	0.0098 (13)	0.0478 (14)
C23	0.0485 (9)	0.0621 (10)	0.0718 (11)	0.0157 (7)	0.0113 (8)	0.0145 (8)
O5	0.0856 (9)	0.0786 (8)	0.0611 (7)	0.0406 (7)	0.0226 (6)	0.0175 (6)

O4—C23	1.200 (2)	C12—H12C	0.9600
C1—N1	1.4731 (19)	C13—H13A	0.9600
C1—C15	1.509 (2)	C13—H13B	0.9600
C1—C2	1.544 (2)	C13—H13C	0.9600
C1—H1A	0.9800	C14—H14A	0.9600
C2—C3	1.501 (3)	C14—H14B	0.9600
C2—C14	1.518 (3)	C14—H14C	0.9600
C2—H2	0.9800	C15—C16	1.381 (2)
C3—O1	1.208 (2)	C15—C20	1.398 (2)
C3—C4	1.513 (3)	C16—C17	1.375 (3)
C4—C13	1.522 (3)	C16—H16	0.9300
C4—C5	1.546 (2)	C17—C18	1.369 (3)
C4—H4	0.9800	C17—H17	0.9300
C5—N1	1.4748 (19)	C18—C19	1.372 (3)
C5—C6	1.515 (2)	C18—H18	0.9300
C5—H5	0.9800	C19—C20	1.381 (3)
C6—C11	1.380 (2)	C19—H19	0.9300
C6—C7	1.404 (2)	C20—O3	1.378 (2)
C7—O2	1.362 (2)	C21—O3	1.407 (2)
C7—C8	1.387 (3)	C21—H21A	0.9600
C8—C9	1.372 (3)	C21—H21B	0.9600
C8—H8	0.9300	C21—H21C	0.9600
C9—C10	1.371 (3)	N1—H1	0.869 (17)
C9—H9	0.9300	C22—C23	1.485 (3)
C10—C11	1.382 (3)	C22—H22A	0.9600
C10—H10	0.9300	C22—H22B	0.9600
C11—H11	0.9300	C22—H22C	0.9600
C12—O2	1.427 (2)	C23—O5	1.298 (2)
C12—H12A	0.9600	O5—H5A	0.8200
C12—H12B	0.9600
N1—C1—C15	110.18 (11)	C4—C13—H13A	109.5
N1—C1—C2	112.74 (13)	C4—C13—H13B	109.5
C15—C1—C2	113.26 (13)	H13A—C13—H13B	109.5
N1—C1—H1A	106.7	C4—C13—H13C	109.5
C15—C1—H1A	106.7	H13A—C13—H13C	109.5
C2—C1—H1A	106.7	H13B—C13—H13C	109.5
C3—C2—C14	113.04 (15)	C2—C14—H14A	109.5
C3—C2—C1	107.96 (13)	C2—C14—H14B	109.5
C14—C2—C1	112.43 (18)	H14A—C14—H14B	109.5
C3—C2—H2	107.7	C2—C14—H14C	109.5
C14—C2—H2	107.7	H14A—C14—H14C	109.5
C1—C2—H2	107.7	H14B—C14—H14C	109.5
O1—C3—C2	122.82 (18)	C16—C15—C20	117.43 (16)
O1—C3—C4	121.76 (18)	C16—C15—C1	120.30 (14)
C2—C3—C4	115.39 (14)	C20—C15—C1	122.27 (15)
C3—C4—C13	112.14 (15)	C17—C16—C15	121.94 (17)
C3—C4—C5	108.37 (13)	C17—C16—H16	119.0
C13—C4—C5	111.53 (16)	C15—C16—H16	119.0
C3—C4—H4	108.2	C18—C17—C16	119.30 (19)
C13—C4—H4	108.2	C18—C17—H17	120.4
C5—C4—H4	108.2	C16—C17—H17	120.4
N1—C5—C6	110.18 (11)	C17—C18—C19	120.87 (19)
N1—C5—C4	114.00 (13)	C17—C18—H18	119.6
C6—C5—C4	112.25 (12)	C19—C18—H18	119.6
N1—C5—H5	106.6	C18—C19—C20	119.44 (17)
C6—C5—H5	106.6	C18—C19—H19	120.3
C4—C5—H5	106.6	C20—C19—H19	120.3
C11—C6—C7	117.73 (15)	O3—C20—C19	123.47 (15)
C11—C6—C5	119.99 (14)	O3—C20—C15	115.54 (15)
C7—C6—C5	122.28 (15)	C19—C20—C15	120.99 (16)
O2—C7—C8	123.97 (16)	O3—C21—H21A	109.5
O2—C7—C6	115.70 (14)	O3—C21—H21B	109.5
C8—C7—C6	120.33 (18)	H21A—C21—H21B	109.5
C9—C8—C7	119.97 (19)	O3—C21—H21C	109.5
C9—C8—H8	120.0	H21A—C21—H21C	109.5
C7—C8—H8	120.0	H21B—C21—H21C	109.5
C8—C9—C10	120.81 (18)	C1—N1—C5	113.75 (11)
C8—C9—H9	119.6	C1—N1—H1	109.1 (11)
C10—C9—H9	119.6	C5—N1—H1	110.0 (11)
C9—C10—C11	119.2 (2)	C7—O2—C12	118.78 (15)
C9—C10—H10	120.4	C20—O3—C21	118.41 (15)
C11—C10—H10	120.4	C23—C22—H22A	109.5
C6—C11—C10	121.98 (18)	C23—C22—H22B	109.5
C6—C11—H11	119.0	H22A—C22—H22B	109.5
C10—C11—H11	119.0	C23—C22—H22C	109.5
O2—C12—H12A	109.5	H22A—C22—H22C	109.5
O2—C12—H12B	109.5	H22B—C22—H22C	109.5
H12A—C12—H12B	109.5	O4—C23—O5	121.44 (16)
O2—C12—H12C	109.5	O4—C23—C22	122.88 (18)
H12A—C12—H12C	109.5	O5—C23—C22	115.69 (17)
H12B—C12—H12C	109.5	C23—O5—H5A	109.5
N1—C1—C2—C3	53.96 (16)	C8—C9—C10—C11	−0.2 (3)
C15—C1—C2—C3	179.92 (12)	C7—C6—C11—C10	−0.2 (3)
N1—C1—C2—C14	179.33 (14)	C5—C6—C11—C10	179.02 (16)
C15—C1—C2—C14	−54.70 (18)	C9—C10—C11—C6	0.7 (3)
C14—C2—C3—O1	−3.6 (3)	N1—C1—C15—C16	−117.88 (16)
C1—C2—C3—O1	121.43 (18)	C2—C1—C15—C16	114.79 (18)
C14—C2—C3—C4	178.51 (16)	N1—C1—C15—C20	62.78 (19)
C1—C2—C3—C4	−56.48 (18)	C2—C1—C15—C20	−64.54 (19)
O1—C3—C4—C13	−0.3 (2)	C20—C15—C16—C17	0.1 (3)
C2—C3—C4—C13	177.66 (15)	C1—C15—C16—C17	−179.23 (18)
O1—C3—C4—C5	−123.82 (18)	C15—C16—C17—C18	−1.3 (3)
C2—C3—C4—C5	54.13 (19)	C16—C17—C18—C19	1.2 (3)
C3—C4—C5—N1	−49.38 (17)	C17—C18—C19—C20	0.0 (3)
C13—C4—C5—N1	−173.28 (13)	C18—C19—C20—O3	179.78 (18)
C3—C4—C5—C6	−175.55 (13)	C18—C19—C20—C15	−1.1 (3)
C13—C4—C5—C6	60.54 (18)	C16—C15—C20—O3	−179.77 (15)
N1—C5—C6—C11	124.36 (15)	C1—C15—C20—O3	−0.4 (2)
C4—C5—C6—C11	−107.43 (17)	C16—C15—C20—C19	1.1 (3)
N1—C5—C6—C7	−56.50 (18)	C1—C15—C20—C19	−179.58 (16)
C4—C5—C6—C7	71.71 (18)	C15—C1—N1—C5	179.12 (12)
C11—C6—C7—O2	179.10 (14)	C2—C1—N1—C5	−53.27 (16)
C5—C6—C7—O2	−0.1 (2)	C6—C5—N1—C1	178.43 (12)
C11—C6—C7—C8	−0.8 (2)	C4—C5—N1—C1	51.18 (16)
C5—C6—C7—C8	−179.95 (15)	C8—C7—O2—C12	−0.2 (3)
O2—C7—C8—C9	−178.64 (17)	C6—C7—O2—C12	179.87 (16)
C6—C7—C8—C9	1.2 (3)	C19—C20—O3—C21	−16.0 (3)
C7—C8—C9—C10	−0.7 (3)	C15—C20—O3—C21	164.90 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···N1i	0.82	1.82	2.642 (2)	178
N1—H1···O2	0.869 (18)	2.210 (16)	2.835 (2)	128.6 (14)
N1—H1···O3	0.869 (17)	2.322 (18)	2.9241 (17)	126.6 (14)
C19—H19···O4ii	0.93	2.51	3.441 (2)	175
C22—H22C···O5iii	0.96	2.54	3.482 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯N1i	0.82	1.82	2.642 (2)	178
N1—H1⋯O2	0.869 (18)	2.210 (16)	2.835 (2)	128.6 (14)
N1—H1⋯O3	0.869 (17)	2.322 (18)	2.9241 (17)	126.6 (14)
C19—H19⋯O4ii	0.93	2.51	3.441 (2)	175
C22—H22C⋯O5iii	0.96	2.54	3.482 (3)	167

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