r-2,c-6-Bis(4-methoxy-phenyl)-c-3,t-3-dimethyl-1-nitro-sopiperidin-4-one.

In the title compound, C(21)H(24)N(2)O(4), the piperidine ring adopts a distorted boat conformation. The crystal structure is stabilized by C-H⋯π inter-actions involving one of the methoxy-phenyl rings.

Related literature

For the biological activity of piperidones, see: Dimmock et al. (1990 ▶); Mutus et al. (1989 ▶); Perumal et al. (2001 ▶). For ring conformations, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C21H24N2O4

M = 368.42

Orthorhombic,

a = 7.2540 (3) Å

b = 15.0469 (6) Å

c = 17.0741 (7) Å

V = 1863.64 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.973, T max = 0.982

24656 measured reflections

3211 independent reflections

2595 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.03

3211 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.15 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019357/ci2805sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019357/ci2805Isup2.hkl

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

C21H24N2O4	F(000) = 784
Mr = 368.42	Dx = 1.313 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3211 reflections
a = 7.2540 (3) Å	θ = 2.4–30.5°
b = 15.0469 (6) Å	µ = 0.09 mm−1
c = 17.0741 (7) Å	T = 293 K
V = 1863.64 (13) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Bruker Kappa-APEXII CCD area-detector diffractometer	3211 independent reflections
Radiation source: fine-focus sealed tube	2595 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 30.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.973, Tmax = 0.982	k = −21→21
24656 measured reflections	l = −24→24

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0532P)2 + 0.2754P] where P = (Fo2 + 2Fc2)/3
3211 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.15 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
N1	0.0483 (2)	0.52808 (12)	0.21105 (9)	0.0433 (4)
C2	0.1305 (2)	0.58054 (13)	0.27489 (10)	0.0417 (4)
H2	0.0276	0.6015	0.3072	0.050*
C3	0.2206 (3)	0.66398 (14)	0.23982 (11)	0.0453 (4)
C4	0.3709 (3)	0.63719 (14)	0.18259 (11)	0.0478 (4)
C5	0.3450 (3)	0.54846 (14)	0.14164 (11)	0.0464 (4)
H5A	0.4235	0.5054	0.1675	0.056*
H5B	0.3898	0.5547	0.0884	0.056*
C6	0.1494 (3)	0.50917 (13)	0.13767 (10)	0.0419 (4)
H6	0.0840	0.5392	0.0950	0.050*
N7	−0.1331 (2)	0.51769 (14)	0.21570 (12)	0.0589 (5)
C8	0.2461 (3)	0.52025 (13)	0.32719 (10)	0.0413 (4)
C9	0.4369 (3)	0.51945 (15)	0.33242 (11)	0.0461 (4)
H9	0.5048	0.5589	0.3020	0.055*
C10	0.5290 (3)	0.46138 (15)	0.38177 (12)	0.0500 (5)
H10	0.6571	0.4620	0.3837	0.060*
C11	0.4317 (3)	0.40259 (13)	0.42807 (12)	0.0484 (4)
C12	0.2405 (3)	0.40122 (16)	0.42284 (13)	0.0562 (5)
H12	0.1730	0.3611	0.4528	0.067*
C13	0.1513 (3)	0.45897 (15)	0.37357 (12)	0.0517 (5)
H13	0.0233	0.4573	0.3710	0.062*
C15	0.2886 (4)	0.72672 (16)	0.30428 (13)	0.0581 (5)
H15A	0.3445	0.7781	0.2809	0.087*
H15B	0.3777	0.6965	0.3362	0.087*
H15C	0.1863	0.7449	0.3361	0.087*
C14	0.0774 (3)	0.71461 (16)	0.18933 (14)	0.0578 (5)
H14A	0.1337	0.7666	0.1673	0.087*
H14B	−0.0251	0.7319	0.2215	0.087*
H14C	0.0347	0.6767	0.1479	0.087*
C16	0.1535 (2)	0.41093 (12)	0.11881 (10)	0.0393 (4)
C17	0.2309 (3)	0.34891 (14)	0.16965 (10)	0.0449 (4)
H17	0.2793	0.3677	0.2173	0.054*
C18	0.2366 (3)	0.26016 (14)	0.15030 (11)	0.0443 (4)
H18	0.2889	0.2195	0.1848	0.053*
C19	0.1647 (2)	0.23100 (12)	0.07945 (10)	0.0402 (4)
C20	0.0887 (3)	0.29189 (13)	0.02797 (11)	0.0430 (4)
H20	0.0414	0.2731	−0.0199	0.052*
C21	0.0838 (3)	0.38045 (14)	0.04814 (10)	0.0431 (4)
H21	0.0322	0.4210	0.0134	0.052*
C22	0.7010 (4)	0.34767 (19)	0.49303 (17)	0.0719 (7)
H22A	0.7349	0.3045	0.5318	0.108*
H22B	0.7358	0.4059	0.5107	0.108*
H22C	0.7632	0.3346	0.4448	0.108*
C23	0.1004 (4)	0.10995 (15)	−0.00595 (14)	0.0605 (6)
H23A	0.1152	0.0466	−0.0089	0.091*
H23B	0.1638	0.1374	−0.0490	0.091*
H23C	−0.0283	0.1245	−0.0085	0.091*
O1	0.5033 (3)	0.68301 (12)	0.16938 (12)	0.0732 (5)
O2	−0.2050 (2)	0.48520 (14)	0.15739 (11)	0.0753 (5)
O3	0.5071 (3)	0.34479 (11)	0.48087 (10)	0.0640 (4)
O4	0.1751 (2)	0.14144 (9)	0.06582 (8)	0.0509 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0311 (6)	0.0576 (9)	0.0412 (7)	0.0002 (7)	0.0008 (6)	−0.0093 (7)
C2	0.0358 (8)	0.0543 (10)	0.0348 (8)	−0.0009 (8)	0.0034 (7)	−0.0084 (7)
C3	0.0446 (9)	0.0519 (10)	0.0393 (8)	0.0004 (8)	0.0037 (8)	−0.0051 (8)
C4	0.0461 (10)	0.0531 (11)	0.0442 (9)	−0.0003 (9)	0.0077 (8)	0.0035 (8)
C5	0.0432 (9)	0.0573 (11)	0.0387 (8)	0.0012 (9)	0.0088 (8)	−0.0034 (8)
C6	0.0403 (8)	0.0522 (10)	0.0331 (8)	0.0041 (8)	−0.0015 (7)	−0.0029 (7)
N7	0.0347 (8)	0.0767 (12)	0.0654 (11)	−0.0027 (8)	−0.0038 (8)	−0.0179 (10)
C8	0.0390 (8)	0.0525 (11)	0.0323 (7)	−0.0055 (8)	0.0015 (7)	−0.0049 (8)
C9	0.0401 (9)	0.0592 (11)	0.0389 (9)	−0.0079 (9)	0.0024 (7)	0.0025 (9)
C10	0.0432 (9)	0.0621 (12)	0.0449 (10)	−0.0046 (9)	−0.0008 (9)	−0.0002 (9)
C11	0.0600 (12)	0.0453 (10)	0.0400 (9)	−0.0028 (9)	0.0003 (9)	−0.0036 (8)
C12	0.0600 (12)	0.0569 (12)	0.0516 (11)	−0.0158 (10)	0.0075 (10)	0.0059 (10)
C13	0.0410 (9)	0.0638 (13)	0.0504 (10)	−0.0121 (10)	0.0056 (9)	0.0009 (10)
C15	0.0579 (12)	0.0581 (12)	0.0582 (12)	−0.0077 (10)	0.0029 (11)	−0.0143 (10)
C14	0.0607 (13)	0.0600 (12)	0.0527 (11)	0.0116 (11)	−0.0001 (11)	−0.0026 (10)
C16	0.0356 (8)	0.0494 (9)	0.0329 (7)	0.0046 (8)	−0.0010 (7)	−0.0024 (7)
C17	0.0425 (9)	0.0604 (11)	0.0319 (8)	0.0043 (9)	−0.0063 (7)	−0.0014 (8)
C18	0.0390 (9)	0.0555 (11)	0.0383 (8)	0.0070 (8)	−0.0033 (7)	0.0074 (8)
C19	0.0324 (8)	0.0480 (9)	0.0403 (8)	0.0009 (7)	0.0050 (7)	0.0008 (7)
C20	0.0420 (9)	0.0533 (10)	0.0336 (8)	0.0022 (8)	−0.0047 (7)	−0.0021 (8)
C21	0.0432 (9)	0.0523 (10)	0.0337 (8)	0.0060 (8)	−0.0065 (7)	0.0020 (8)
C22	0.0729 (16)	0.0707 (16)	0.0723 (15)	0.0205 (14)	−0.0010 (14)	0.0133 (13)
C23	0.0649 (13)	0.0527 (12)	0.0638 (13)	−0.0002 (11)	−0.0052 (12)	−0.0134 (11)
O1	0.0684 (10)	0.0652 (10)	0.0858 (13)	−0.0185 (9)	0.0299 (10)	−0.0047 (9)
O2	0.0420 (8)	0.1026 (14)	0.0812 (11)	0.0025 (9)	−0.0132 (8)	−0.0327 (11)
O3	0.0740 (11)	0.0592 (9)	0.0589 (9)	−0.0050 (9)	−0.0057 (9)	0.0118 (8)
O4	0.0543 (8)	0.0467 (7)	0.0516 (7)	0.0036 (6)	−0.0011 (7)	0.0001 (6)

N1—N7	1.328 (2)	C13—H13	0.93
N1—C2	1.472 (2)	C15—H15A	0.96
N1—C6	1.479 (2)	C15—H15B	0.96
C2—C8	1.524 (3)	C15—H15C	0.96
C2—C3	1.537 (3)	C14—H14A	0.96
C2—H2	0.98	C14—H14B	0.96
C3—C4	1.519 (3)	C14—H14C	0.96
C3—C15	1.532 (3)	C16—C21	1.386 (2)
C3—C14	1.550 (3)	C16—C17	1.393 (3)
C4—O1	1.204 (2)	C17—C18	1.376 (3)
C4—C5	1.519 (3)	C17—H17	0.93
C5—C6	1.539 (3)	C18—C19	1.389 (3)
C5—H5A	0.97	C18—H18	0.93
C5—H5B	0.97	C19—O4	1.370 (2)
C6—C16	1.513 (3)	C19—C20	1.384 (3)
C6—H6	0.98	C20—C21	1.377 (3)
N7—O2	1.225 (2)	C20—H20	0.93
C8—C9	1.387 (3)	C21—H21	0.93
C8—C13	1.396 (3)	C22—O3	1.423 (3)
C9—C10	1.385 (3)	C22—H22A	0.96
C9—H9	0.93	C22—H22B	0.96
C10—C11	1.380 (3)	C22—H22C	0.96
C10—H10	0.93	C23—O4	1.421 (3)
C11—O3	1.367 (3)	C23—H23A	0.96
C11—C12	1.390 (3)	C23—H23B	0.96
C12—C13	1.372 (3)	C23—H23C	0.96
C12—H12	0.93
N7—N1—C2	114.87 (16)	C12—C13—H13	118.9
N7—N1—C6	121.28 (17)	C8—C13—H13	118.9
C2—N1—C6	121.97 (14)	C3—C15—H15A	109.5
N1—C2—C8	109.72 (15)	C3—C15—H15B	109.5
N1—C2—C3	108.78 (15)	H15A—C15—H15B	109.5
C8—C2—C3	118.74 (16)	C3—C15—H15C	109.5
N1—C2—H2	106.3	H15A—C15—H15C	109.5
C8—C2—H2	106.3	H15B—C15—H15C	109.5
C3—C2—H2	106.3	C3—C14—H14A	109.5
C4—C3—C15	113.24 (18)	C3—C14—H14B	109.5
C4—C3—C2	109.81 (16)	H14A—C14—H14B	109.5
C15—C3—C2	111.14 (16)	C3—C14—H14C	109.5
C4—C3—C14	104.71 (16)	H14A—C14—H14C	109.5
C15—C3—C14	108.22 (18)	H14B—C14—H14C	109.5
C2—C3—C14	109.47 (17)	C21—C16—C17	117.90 (17)
O1—C4—C5	121.09 (19)	C21—C16—C6	120.07 (16)
O1—C4—C3	122.78 (19)	C17—C16—C6	122.00 (16)
C5—C4—C3	116.13 (17)	C18—C17—C16	120.84 (17)
C4—C5—C6	118.19 (17)	C18—C17—H17	119.6
C4—C5—H5A	107.8	C16—C17—H17	119.6
C6—C5—H5A	107.8	C17—C18—C19	120.29 (18)
C4—C5—H5B	107.8	C17—C18—H18	119.9
C6—C5—H5B	107.8	C19—C18—H18	119.9
H5A—C5—H5B	107.1	O4—C19—C20	124.43 (17)
N1—C6—C16	112.22 (16)	O4—C19—C18	115.98 (17)
N1—C6—C5	110.23 (15)	C20—C19—C18	119.58 (18)
C16—C6—C5	111.48 (16)	C21—C20—C19	119.48 (17)
N1—C6—H6	107.6	C21—C20—H20	120.3
C16—C6—H6	107.6	C19—C20—H20	120.3
C5—C6—H6	107.6	C20—C21—C16	121.90 (17)
O2—N7—N1	114.82 (19)	C20—C21—H21	119.1
C9—C8—C13	116.69 (19)	C16—C21—H21	119.1
C9—C8—C2	126.27 (18)	O3—C22—H22A	109.5
C13—C8—C2	117.03 (17)	O3—C22—H22B	109.5
C10—C9—C8	121.70 (19)	H22A—C22—H22B	109.5
C10—C9—H9	119.2	O3—C22—H22C	109.5
C8—C9—H9	119.2	H22A—C22—H22C	109.5
C11—C10—C9	120.41 (19)	H22B—C22—H22C	109.5
C11—C10—H10	119.8	O4—C23—H23A	109.5
C9—C10—H10	119.8	O4—C23—H23B	109.5
O3—C11—C10	125.5 (2)	H23A—C23—H23B	109.5
O3—C11—C12	115.6 (2)	O4—C23—H23C	109.5
C10—C11—C12	118.9 (2)	H23A—C23—H23C	109.5
C13—C12—C11	120.0 (2)	H23B—C23—H23C	109.5
C13—C12—H12	120.0	C11—O3—C22	118.20 (19)
C11—C12—H12	120.0	C19—O4—C23	116.96 (16)
C12—C13—C8	122.26 (19)
N7—N1—C2—C8	110.4 (2)	C3—C2—C8—C13	164.11 (17)
C6—N1—C2—C8	−85.0 (2)	C13—C8—C9—C10	−0.6 (3)
N7—N1—C2—C3	−118.2 (2)	C2—C8—C9—C10	−179.66 (17)
C6—N1—C2—C3	46.4 (2)	C8—C9—C10—C11	−0.6 (3)
N1—C2—C3—C4	−60.6 (2)	C9—C10—C11—O3	−177.43 (19)
C8—C2—C3—C4	65.7 (2)	C9—C10—C11—C12	1.6 (3)
N1—C2—C3—C15	173.29 (16)	O3—C11—C12—C13	177.69 (18)
C8—C2—C3—C15	−60.3 (2)	C10—C11—C12—C13	−1.4 (3)
N1—C2—C3—C14	53.80 (19)	C11—C12—C13—C8	0.2 (3)
C8—C2—C3—C14	−179.83 (16)	C9—C8—C13—C12	0.8 (3)
C15—C3—C4—O1	−26.9 (3)	C2—C8—C13—C12	179.92 (19)
C2—C3—C4—O1	−151.7 (2)	N1—C6—C16—C21	122.51 (18)
C14—C3—C4—O1	90.8 (3)	C5—C6—C16—C21	−113.29 (19)
C15—C3—C4—C5	153.57 (19)	N1—C6—C16—C17	−59.4 (2)
C2—C3—C4—C5	28.7 (2)	C5—C6—C16—C17	64.8 (2)
C14—C3—C4—C5	−88.7 (2)	C21—C16—C17—C18	−0.4 (3)
O1—C4—C5—C6	−158.8 (2)	C6—C16—C17—C18	−178.54 (18)
C3—C4—C5—C6	20.8 (3)	C16—C17—C18—C19	−0.1 (3)
N7—N1—C6—C16	−69.4 (2)	C17—C18—C19—O4	−179.38 (18)
C2—N1—C6—C16	127.05 (19)	C17—C18—C19—C20	0.6 (3)
N7—N1—C6—C5	165.7 (2)	O4—C19—C20—C21	179.33 (18)
C2—N1—C6—C5	2.1 (2)	C18—C19—C20—C21	−0.7 (3)
C4—C5—C6—N1	−37.0 (2)	C19—C20—C21—C16	0.2 (3)
C4—C5—C6—C16	−162.27 (16)	C17—C16—C21—C20	0.3 (3)
C2—N1—N7—O2	170.12 (19)	C6—C16—C21—C20	178.52 (18)
C6—N1—N7—O2	5.4 (3)	C10—C11—O3—C22	3.6 (3)
N1—C2—C8—C9	109.0 (2)	C12—C11—O3—C22	−175.5 (2)
C3—C2—C8—C9	−16.9 (3)	C20—C19—O4—C23	−0.7 (3)
N1—C2—C8—C13	−70.0 (2)	C18—C19—O4—C23	179.28 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···Cg1i	0.96	2.97	3.9108 (26)	167
C23—H23C···Cg1ii	0.96	2.86	3.7201 (27)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯Cg1i	0.96	2.97	3.9108 (26)	167
C23—H23C⋯Cg1ii	0.96	2.86	3.7201 (27)	149

Symmetry codes: (i) ; (ii) .