Crystal structure of 2,6-bis-(2,5-di-meth-oxy-phen-yl)-3,5-di-methyl-piperidin-4-one.

In the title mol-ecule, C23H29NO5, the central piperidine ring has a chair conformation. The planes of the two benzene rings are inclined each to other at 61.7 (1)°. The crystal packing exhibits no directional inter-actions only van der Waals contacts.

Related literature

For the synthesis, stereochemistry and biological actions of piperidin-4-ones, see: Sahu et al. (2013 ▶); Parthiban et al. (2011 ▶). For a related crystal structure, see: Parthiban et al. (2008 ▶).

Experimental

Crystal data

C23H29NO5

M = 399.47

Monoclinic,

a = 11.1358 (7) Å

b = 9.4756 (5) Å

c = 20.4541 (11) Å

β = 92.271 (2)°

V = 2156.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.979, T max = 0.987

11151 measured reflections

3536 independent reflections

2262 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.116

S = 0.98

3536 reflections

272 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814022041/cv5470sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814022041/cv5470Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814022041/cv5470Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814022041/cv5470fig1.tif

View of (I) showing the atomic numbering and 30% probability displacement ellipsoids.

CCDC reference: 1027842

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

C23H29NO5	Z = 4
Mr = 399.47	F(000) = 856
Monoclinic, P21/c	Dx = 1.230 Mg m−3
a = 11.1358 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4756 (5) Å	µ = 0.09 mm−1
c = 20.4541 (11) Å	T = 298 K
β = 92.271 (2)°	Block, yellow
V = 2156.6 (2) Å3	0.25 × 0.20 × 0.15 mm

Bruker APEXII CCD area-detector diffractometer	2262 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.029
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θmax = 25.0°, θmin = 2.4°
Tmin = 0.979, Tmax = 0.987	h = −12→12
11151 measured reflections	k = −11→10
3536 independent reflections	l = −20→24

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0405P)2 + 0.9547P] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
3536 reflections	Δρmax = 0.17 e Å−3
272 parameters	Δρmin = −0.18 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.

	x	y	z	Uiso*/Ueq
C1	0.54320 (17)	0.4952 (2)	0.14728 (9)	0.0380 (5)
H1	0.5445	0.3918	0.1468	0.046*
C2	0.59048 (18)	0.5485 (2)	0.21515 (10)	0.0439 (5)
H2	0.5876	0.6519	0.2147	0.053*
C3	0.50346 (19)	0.4971 (2)	0.26472 (10)	0.0447 (6)
C4	0.37508 (18)	0.5434 (3)	0.25295 (10)	0.0465 (6)
H4	0.3737	0.6469	0.2526	0.056*
C5	0.33417 (17)	0.4916 (2)	0.18398 (9)	0.0413 (5)
H5	0.3343	0.3882	0.1834	0.050*
C6	0.61644 (17)	0.5504 (2)	0.09201 (9)	0.0369 (5)
C7	0.6022 (2)	0.6895 (2)	0.07205 (10)	0.0461 (6)
H7	0.5514	0.7484	0.0946	0.055*
C8	0.6620 (2)	0.7426 (2)	0.01924 (11)	0.0510 (6)
C9	0.7397 (2)	0.6581 (3)	−0.01319 (10)	0.0520 (6)
H9	0.7807	0.6936	−0.0484	0.062*
C10	0.7570 (2)	0.5200 (3)	0.00665 (10)	0.0495 (6)
H10	0.8106	0.4631	−0.0150	0.059*
C11	0.69529 (18)	0.4653 (2)	0.05833 (9)	0.0404 (5)
C12	0.6457 (4)	0.9225 (3)	−0.06178 (14)	0.1112 (13)
H12A	0.7285	0.9324	−0.0725	0.167*
H12B	0.6053	1.0112	−0.0681	0.167*
H12C	0.6080	0.8525	−0.0896	0.167*
C13	0.7419 (4)	0.2273 (3)	0.03408 (15)	0.1146 (14)
H13A	0.6913	0.2362	−0.0048	0.172*
H13B	0.7329	0.1347	0.0523	0.172*
H13C	0.8242	0.2416	0.0233	0.172*
C14	0.7187 (2)	0.5047 (3)	0.23158 (12)	0.0684 (8)
H14A	0.7390	0.5282	0.2763	0.103*
H14B	0.7718	0.5533	0.2034	0.103*
H14C	0.7266	0.4047	0.2255	0.103*
C15	0.2921 (2)	0.4933 (3)	0.30574 (12)	0.0722 (8)
H15A	0.2847	0.3924	0.3037	0.108*
H15B	0.2143	0.5355	0.2988	0.108*
H15C	0.3251	0.5203	0.3480	0.108*
C16	0.20999 (18)	0.5443 (2)	0.16386 (10)	0.0425 (5)
C17	0.10969 (19)	0.4552 (3)	0.16077 (11)	0.0487 (6)
C18	0.0001 (2)	0.5069 (3)	0.13831 (12)	0.0595 (7)
H18	−0.0658	0.4466	0.1353	0.071*
C19	−0.0138 (2)	0.6459 (3)	0.12020 (12)	0.0610 (7)
H19	−0.0886	0.6794	0.1055	0.073*
C20	0.0835 (2)	0.7349 (3)	0.12398 (11)	0.0534 (6)
C21	0.1949 (2)	0.6839 (3)	0.14593 (10)	0.0480 (6)
H21	0.2604	0.7448	0.1486	0.058*
C22	0.0276 (3)	0.2382 (4)	0.19599 (19)	0.1093 (13)
H22A	−0.0150	0.2881	0.2287	0.164*
H22B	0.0536	0.1484	0.2131	0.164*
H22C	−0.0244	0.2240	0.1580	0.164*
C23	−0.0296 (3)	0.9292 (4)	0.08139 (18)	0.1084 (12)
H23A	−0.0539	0.8772	0.0428	0.163*
H23B	−0.0200	1.0270	0.0704	0.163*
H23C	−0.0897	0.9201	0.1135	0.163*
N1	0.41929 (15)	0.5441 (2)	0.13674 (9)	0.0418 (5)
O1	0.6391 (2)	0.88138 (18)	0.00307 (9)	0.0849 (6)
O2	0.70918 (15)	0.32842 (17)	0.07975 (7)	0.0610 (5)
O3	0.53408 (14)	0.4179 (2)	0.30899 (8)	0.0667 (5)
O4	0.12791 (14)	0.31712 (18)	0.17881 (9)	0.0684 (5)
O5	0.08013 (16)	0.8756 (2)	0.10695 (10)	0.0790 (6)
H1N	0.3918 (19)	0.522 (2)	0.0956 (11)	0.054 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0316 (12)	0.0430 (13)	0.0398 (12)	−0.0014 (10)	0.0056 (9)	−0.0003 (9)
C2	0.0343 (13)	0.0565 (14)	0.0410 (12)	−0.0045 (11)	0.0012 (9)	0.0011 (10)
C3	0.0425 (14)	0.0560 (15)	0.0355 (12)	−0.0051 (11)	0.0007 (10)	−0.0054 (11)
C4	0.0396 (14)	0.0601 (15)	0.0405 (12)	0.0024 (11)	0.0086 (10)	−0.0017 (11)
C5	0.0325 (13)	0.0491 (14)	0.0428 (12)	−0.0005 (10)	0.0065 (9)	−0.0020 (10)
C6	0.0293 (12)	0.0436 (13)	0.0378 (11)	−0.0002 (10)	0.0020 (9)	−0.0019 (9)
C7	0.0478 (14)	0.0469 (15)	0.0442 (13)	0.0044 (11)	0.0081 (10)	−0.0026 (10)
C8	0.0621 (16)	0.0460 (15)	0.0452 (13)	−0.0051 (13)	0.0062 (12)	0.0016 (11)
C9	0.0586 (16)	0.0618 (17)	0.0364 (12)	−0.0123 (13)	0.0106 (11)	0.0012 (11)
C10	0.0435 (14)	0.0636 (17)	0.0422 (13)	0.0039 (12)	0.0122 (10)	−0.0060 (11)
C11	0.0377 (13)	0.0461 (14)	0.0374 (11)	0.0030 (11)	0.0028 (10)	−0.0005 (10)
C12	0.191 (4)	0.077 (2)	0.065 (2)	0.003 (2)	0.001 (2)	0.0232 (16)
C13	0.212 (4)	0.059 (2)	0.075 (2)	0.041 (2)	0.034 (2)	−0.0018 (16)
C14	0.0398 (15)	0.111 (2)	0.0547 (15)	−0.0071 (15)	−0.0020 (11)	0.0093 (15)
C15	0.0505 (16)	0.117 (2)	0.0500 (15)	0.0073 (16)	0.0181 (12)	0.0062 (15)
C16	0.0325 (13)	0.0549 (15)	0.0407 (12)	0.0019 (11)	0.0079 (9)	−0.0023 (10)
C17	0.0326 (14)	0.0611 (17)	0.0530 (14)	0.0022 (12)	0.0087 (10)	−0.0008 (12)
C18	0.0338 (15)	0.0736 (19)	0.0712 (17)	−0.0039 (13)	0.0049 (12)	0.0005 (14)
C19	0.0351 (15)	0.083 (2)	0.0648 (17)	0.0121 (15)	0.0022 (12)	0.0024 (14)
C20	0.0474 (16)	0.0579 (17)	0.0556 (15)	0.0122 (14)	0.0087 (12)	0.0018 (12)
C21	0.0368 (14)	0.0584 (16)	0.0494 (13)	0.0013 (12)	0.0085 (10)	−0.0027 (11)
C22	0.065 (2)	0.098 (3)	0.165 (3)	−0.0243 (19)	0.002 (2)	0.051 (2)
C23	0.096 (3)	0.102 (3)	0.128 (3)	0.043 (2)	0.012 (2)	0.030 (2)
N1	0.0293 (10)	0.0615 (13)	0.0347 (10)	0.0010 (9)	0.0031 (8)	−0.0022 (9)
O1	0.1432 (19)	0.0502 (12)	0.0627 (12)	0.0013 (11)	0.0232 (11)	0.0144 (9)
O2	0.0819 (12)	0.0503 (10)	0.0522 (10)	0.0217 (9)	0.0209 (8)	0.0043 (8)
O3	0.0544 (11)	0.0958 (14)	0.0499 (10)	0.0008 (10)	0.0020 (8)	0.0231 (9)
O4	0.0420 (10)	0.0605 (12)	0.1031 (14)	−0.0078 (9)	0.0086 (9)	0.0132 (10)
O5	0.0660 (13)	0.0680 (13)	0.1032 (15)	0.0206 (10)	0.0044 (10)	0.0128 (11)

C1—N1	1.463 (2)	C13—O2	1.396 (3)
C1—C6	1.513 (3)	C13—H13A	0.9600
C1—C2	1.550 (3)	C13—H13B	0.9600
C1—H1	0.9800	C13—H13C	0.9600
C2—C14	1.511 (3)	C14—H14A	0.9600
C2—C3	1.511 (3)	C14—H14B	0.9600
C2—H2	0.9800	C14—H14C	0.9600
C3—O3	1.215 (2)	C15—H15A	0.9600
C3—C4	1.506 (3)	C15—H15B	0.9600
C4—C15	1.525 (3)	C15—H15C	0.9600
C4—C5	1.545 (3)	C16—C21	1.381 (3)
C4—H4	0.9800	C16—C17	1.399 (3)
C5—N1	1.467 (2)	C17—O4	1.373 (3)
C5—C16	1.512 (3)	C17—C18	1.377 (3)
C5—H5	0.9800	C18—C19	1.376 (3)
C6—C7	1.388 (3)	C18—H18	0.9300
C6—C11	1.394 (3)	C19—C20	1.372 (3)
C7—C8	1.386 (3)	C19—H19	0.9300
C7—H7	0.9300	C20—O5	1.378 (3)
C8—C9	1.369 (3)	C20—C21	1.389 (3)
C8—O1	1.378 (3)	C21—H21	0.9300
C9—C10	1.381 (3)	C22—O4	1.400 (3)
C9—H9	0.9300	C22—H22A	0.9600
C10—C11	1.384 (3)	C22—H22B	0.9600
C10—H10	0.9300	C22—H22C	0.9600
C11—O2	1.376 (2)	C23—O5	1.405 (3)
C12—O1	1.387 (3)	C23—H23A	0.9600
C12—H12A	0.9600	C23—H23B	0.9600
C12—H12B	0.9600	C23—H23C	0.9600
C12—H12C	0.9600	N1—H1N	0.91 (2)
N1—C1—C6	108.28 (16)	H13A—C13—H13B	109.5
N1—C1—C2	108.30 (16)	O2—C13—H13C	109.5
C6—C1—C2	112.50 (16)	H13A—C13—H13C	109.5
N1—C1—H1	109.2	H13B—C13—H13C	109.5
C6—C1—H1	109.2	C2—C14—H14A	109.5
C2—C1—H1	109.2	C2—C14—H14B	109.5
C14—C2—C3	112.79 (18)	H14A—C14—H14B	109.5
C14—C2—C1	113.20 (18)	C2—C14—H14C	109.5
C3—C2—C1	106.98 (16)	H14A—C14—H14C	109.5
C14—C2—H2	107.9	H14B—C14—H14C	109.5
C3—C2—H2	107.9	C4—C15—H15A	109.5
C1—C2—H2	107.9	C4—C15—H15B	109.5
O3—C3—C4	122.4 (2)	H15A—C15—H15B	109.5
O3—C3—C2	122.1 (2)	C4—C15—H15C	109.5
C4—C3—C2	115.40 (18)	H15A—C15—H15C	109.5
C3—C4—C15	113.20 (19)	H15B—C15—H15C	109.5
C3—C4—C5	107.28 (16)	C21—C16—C17	118.5 (2)
C15—C4—C5	112.49 (19)	C21—C16—C5	119.26 (19)
C3—C4—H4	107.9	C17—C16—C5	122.2 (2)
C15—C4—H4	107.9	O4—C17—C18	123.2 (2)
C5—C4—H4	107.9	O4—C17—C16	117.0 (2)
N1—C5—C16	108.48 (17)	C18—C17—C16	119.8 (2)
N1—C5—C4	108.59 (17)	C17—C18—C19	121.3 (2)
C16—C5—C4	112.15 (17)	C17—C18—H18	119.4
N1—C5—H5	109.2	C19—C18—H18	119.4
C16—C5—H5	109.2	C20—C19—C18	119.5 (2)
C4—C5—H5	109.2	C20—C19—H19	120.2
C7—C6—C11	118.11 (19)	C18—C19—H19	120.2
C7—C6—C1	119.29 (18)	C19—C20—O5	124.5 (2)
C11—C6—C1	122.56 (19)	C19—C20—C21	119.8 (2)
C8—C7—C6	121.4 (2)	O5—C20—C21	115.7 (2)
C8—C7—H7	119.3	C16—C21—C20	121.1 (2)
C6—C7—H7	119.3	C16—C21—H21	119.4
C9—C8—O1	123.8 (2)	C20—C21—H21	119.4
C9—C8—C7	119.9 (2)	O4—C22—H22A	109.5
O1—C8—C7	116.3 (2)	O4—C22—H22B	109.5
C8—C9—C10	119.6 (2)	H22A—C22—H22B	109.5
C8—C9—H9	120.2	O4—C22—H22C	109.5
C10—C9—H9	120.2	H22A—C22—H22C	109.5
C11—C10—C9	120.8 (2)	H22B—C22—H22C	109.5
C11—C10—H10	119.6	O5—C23—H23A	109.5
C9—C10—H10	119.6	O5—C23—H23B	109.5
O2—C11—C10	122.92 (19)	H23A—C23—H23B	109.5
O2—C11—C6	116.93 (18)	O5—C23—H23C	109.5
C10—C11—C6	120.1 (2)	H23A—C23—H23C	109.5
O1—C12—H12A	109.5	H23B—C23—H23C	109.5
O1—C12—H12B	109.5	C1—N1—C5	115.22 (16)
H12A—C12—H12B	109.5	C1—N1—H1N	110.3 (13)
O1—C12—H12C	109.5	C5—N1—H1N	109.3 (13)
H12A—C12—H12C	109.5	C8—O1—C12	118.8 (2)
H12B—C12—H12C	109.5	C11—O2—C13	117.55 (19)
O2—C13—H13A	109.5	C17—O4—C22	117.8 (2)
O2—C13—H13B	109.5	C20—O5—C23	117.3 (2)
N1—C1—C2—C14	−179.85 (19)	C7—C6—C11—C10	0.1 (3)
C6—C1—C2—C14	−60.2 (2)	C1—C6—C11—C10	177.74 (19)
N1—C1—C2—C3	55.3 (2)	N1—C5—C16—C21	−45.6 (3)
C6—C1—C2—C3	174.94 (18)	C4—C5—C16—C21	74.4 (2)
C14—C2—C3—O3	−6.6 (3)	N1—C5—C16—C17	132.4 (2)
C1—C2—C3—O3	118.5 (2)	C4—C5—C16—C17	−107.7 (2)
C14—C2—C3—C4	177.1 (2)	C21—C16—C17—O4	179.87 (19)
C1—C2—C3—C4	−57.8 (2)	C5—C16—C17—O4	1.9 (3)
O3—C3—C4—C15	5.9 (3)	C21—C16—C17—C18	1.9 (3)
C2—C3—C4—C15	−177.8 (2)	C5—C16—C17—C18	−176.0 (2)
O3—C3—C4—C5	−118.8 (2)	O4—C17—C18—C19	−179.4 (2)
C2—C3—C4—C5	57.5 (2)	C16—C17—C18—C19	−1.6 (4)
C3—C4—C5—N1	−54.6 (2)	C17—C18—C19—C20	0.6 (4)
C15—C4—C5—N1	−179.68 (19)	C18—C19—C20—O5	179.7 (2)
C3—C4—C5—C16	−174.42 (18)	C18—C19—C20—C21	0.1 (4)
C15—C4—C5—C16	60.5 (3)	C17—C16—C21—C20	−1.3 (3)
N1—C1—C6—C7	44.2 (2)	C5—C16—C21—C20	176.73 (19)
C2—C1—C6—C7	−75.5 (2)	C19—C20—C21—C16	0.3 (3)
N1—C1—C6—C11	−133.4 (2)	O5—C20—C21—C16	−179.4 (2)
C2—C1—C6—C11	106.9 (2)	C6—C1—N1—C5	176.09 (17)
C11—C6—C7—C8	1.5 (3)	C2—C1—N1—C5	−61.6 (2)
C1—C6—C7—C8	−176.22 (19)	C16—C5—N1—C1	−176.60 (17)
C6—C7—C8—C9	−1.9 (3)	C4—C5—N1—C1	61.3 (2)
C6—C7—C8—O1	178.8 (2)	C9—C8—O1—C12	30.9 (4)
O1—C8—C9—C10	179.9 (2)	C7—C8—O1—C12	−149.8 (3)
C7—C8—C9—C10	0.7 (3)	C10—C11—O2—C13	−28.2 (3)
C8—C9—C10—C11	0.9 (3)	C6—C11—O2—C13	153.0 (3)
C9—C10—C11—O2	179.8 (2)	C18—C17—O4—C22	−21.9 (4)
C9—C10—C11—C6	−1.3 (3)	C16—C17—O4—C22	160.3 (2)
C7—C6—C11—O2	179.04 (18)	C19—C20—O5—C23	−2.8 (4)
C1—C6—C11—O2	−3.3 (3)	C21—C20—O5—C23	176.8 (2)