1-Methyl-2,6-cis-distyrylpiperidine.

The complete molecule of the title compound, C(22)H(25)N, is generated by crystallographic mirror symmetry, with two C atoms and the N atom lying on the mirror plane. The central ring adopts a chair conformation and the dihedral angle between the aromatic rings is 56.69 (4)°.

Related literature

The title compound is a des-oxygen lobeline derivative (Zheng et al., 2005 ▶).

Experimental

Crystal data

C22H25N

M = 303.43

Orthorhombic,

a = 17.3766 (2) Å

b = 18.1774 (6) Å

c = 5.5354 (7) Å

V = 1748.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 173 K

0.40 × 0.25 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

12693 measured reflections

2077 independent reflections

1624 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.105

S = 1.10

2077 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049617/hg2598sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049617/hg2598Isup2.hkl

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

C22H25N	F(000) = 656
Mr = 303.43	Dx = 1.153 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 12455 reflections
a = 17.3766 (2) Å	θ = 1.0–27.5°
b = 18.1774 (6) Å	µ = 0.07 mm−1
c = 5.5354 (7) Å	T = 173 K
V = 1748.3 (2) Å3	Irregular block, colourless
Z = 4	0.40 × 0.25 × 0.20 mm

Nonius KappaCCD diffractometer	1624 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
graphite	θmax = 27.5°, θmin = 2.2°
Detector resolution: 18 pixels mm-1	h = −22→22
ω scans at fixed χ = 55°	k = −23→23
12693 measured reflections	l = −7→7
2077 independent reflections

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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0317P)2 + 0.526P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2077 reflections	Δρmax = 0.19 e Å−3
110 parameters	Δρmin = −0.16 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: 0.0098 (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
N1	0.09202 (8)	0.2500	0.1454 (3)	0.0293 (4)
C1	0.14851 (11)	0.2500	0.3409 (4)	0.0380 (5)
H1A	0.1238	0.2500	0.5016	0.046*
H1B	0.1809	0.2955	0.3259	0.046*
C2	0.04374 (7)	0.18311 (6)	0.1549 (2)	0.0291 (3)
H2	0.0129	0.1845	0.3073	0.035*
C3	−0.01177 (8)	0.18156 (7)	−0.0582 (2)	0.0344 (3)
H3A	0.0180	0.1770	−0.2100	0.041*
H3B	−0.0453	0.1378	−0.0443	0.041*
C4	−0.06143 (11)	0.2500	−0.0703 (4)	0.0397 (5)
H4A	−0.0912	0.2500	−0.2228	0.048*
H4B	−0.0983	0.2500	0.0659	0.048*
C5	0.09154 (7)	0.11450 (7)	0.1566 (2)	0.0302 (3)
H5	0.1269	0.1079	0.0274	0.036*
C6	0.08859 (7)	0.06248 (7)	0.3230 (2)	0.0304 (3)
H6	0.0547	0.0709	0.4547	0.036*
C7	0.13201 (7)	−0.00733 (7)	0.3274 (2)	0.0280 (3)
C8	0.12316 (7)	−0.05457 (7)	0.5236 (2)	0.0349 (3)
H8	0.0885	−0.0419	0.6497	0.042*
C9	0.16422 (8)	−0.11997 (7)	0.5374 (3)	0.0412 (4)
H9	0.1574	−0.1517	0.6720	0.049*
C10	0.21478 (8)	−0.13885 (7)	0.3562 (3)	0.0411 (4)
H10	0.2430	−0.1835	0.3655	0.049*
C11	0.22423 (8)	−0.09261 (7)	0.1615 (3)	0.0386 (4)
H11	0.2591	−0.1055	0.0363	0.046*
C12	0.18351 (7)	−0.02768 (7)	0.1467 (2)	0.0330 (3)
H12	0.1907	0.0036	0.0111	0.040*

	U11	U22	U33	U12	U13	U23
N1	0.0269 (8)	0.0241 (8)	0.0369 (9)	0.000	−0.0038 (7)	0.000
C1	0.0347 (10)	0.0307 (10)	0.0486 (12)	0.000	−0.0101 (9)	0.000
C2	0.0291 (6)	0.0251 (7)	0.0332 (7)	−0.0001 (5)	0.0003 (5)	−0.0005 (5)
C3	0.0362 (7)	0.0278 (7)	0.0391 (8)	−0.0025 (6)	−0.0059 (6)	−0.0027 (6)
C4	0.0369 (11)	0.0326 (10)	0.0496 (12)	0.000	−0.0143 (9)	0.000
C5	0.0289 (6)	0.0273 (7)	0.0345 (7)	−0.0013 (5)	0.0019 (6)	−0.0016 (6)
C6	0.0279 (6)	0.0297 (7)	0.0334 (7)	−0.0020 (5)	0.0010 (5)	−0.0031 (6)
C7	0.0254 (6)	0.0242 (6)	0.0342 (7)	−0.0038 (5)	−0.0053 (5)	−0.0012 (5)
C8	0.0314 (7)	0.0371 (7)	0.0361 (8)	−0.0054 (6)	0.0003 (6)	0.0011 (6)
C9	0.0450 (8)	0.0315 (7)	0.0471 (9)	−0.0099 (6)	−0.0089 (7)	0.0125 (7)
C10	0.0385 (8)	0.0220 (7)	0.0628 (10)	0.0007 (6)	−0.0101 (7)	−0.0027 (7)
C11	0.0373 (8)	0.0303 (7)	0.0482 (9)	−0.0008 (6)	0.0012 (7)	−0.0079 (7)
C12	0.0362 (7)	0.0281 (7)	0.0348 (7)	−0.0031 (6)	−0.0005 (6)	0.0015 (6)

N1—C1	1.461 (2)	C5—H5	0.9500
N1—C2i	1.4781 (14)	C6—C7	1.4765 (17)
N1—C2	1.4781 (14)	C6—H6	0.9500
C1—H1A	0.9877	C7—C12	1.3922 (17)
C1—H1B	1.0042	C7—C8	1.3930 (18)
C2—C5	1.4984 (16)	C8—C9	1.3885 (19)
C2—C3	1.5238 (17)	C8—H8	0.9500
C2—H2	1.0000	C9—C10	1.377 (2)
C3—C4	1.5155 (16)	C9—H9	0.9500
C3—H3A	0.9900	C10—C11	1.3765 (19)
C3—H3B	0.9900	C10—H10	0.9500
C4—C3i	1.5154 (16)	C11—C12	1.3785 (18)
C4—H4A	0.9900	C11—H11	0.9500
C4—H4B	0.9900	C12—H12	0.9500
C5—C6	1.3210 (17)
C1—N1—C2i	110.79 (9)	C6—C5—C2	125.35 (12)
C1—N1—C2	110.79 (9)	C6—C5—H5	117.3
C2i—N1—C2	110.68 (13)	C2—C5—H5	117.3
N1—C1—H1A	112.1	C5—C6—C7	127.36 (12)
N1—C1—H1B	108.4	C5—C6—H6	116.3
H1A—C1—H1B	108.5	C7—C6—H6	116.3
N1—C2—C5	111.73 (10)	C12—C7—C8	117.85 (12)
N1—C2—C3	110.30 (11)	C12—C7—C6	123.03 (11)
C5—C2—C3	109.90 (10)	C8—C7—C6	119.10 (12)
N1—C2—H2	108.3	C9—C8—C7	120.93 (13)
C5—C2—H2	108.3	C9—C8—H8	119.5
C3—C2—H2	108.3	C7—C8—H8	119.5
C4—C3—C2	112.31 (11)	C10—C9—C8	120.09 (13)
C4—C3—H3A	109.1	C10—C9—H9	120.0
C2—C3—H3A	109.1	C8—C9—H9	120.0
C4—C3—H3B	109.1	C11—C10—C9	119.61 (13)
C2—C3—H3B	109.1	C11—C10—H10	120.2
H3A—C3—H3B	107.9	C9—C10—H10	120.2
C3i—C4—C3	110.34 (15)	C10—C11—C12	120.55 (13)
C3i—C4—H4A	109.6	C10—C11—H11	119.7
C3—C4—H4A	109.6	C12—C11—H11	119.7
C3i—C4—H4B	109.6	C11—C12—C7	120.97 (12)
C3—C4—H4B	109.6	C11—C12—H12	119.5
H4A—C4—H4B	108.1	C7—C12—H12	119.5
C1—N1—C2—C5	−54.16 (15)	C5—C6—C7—C12	−0.36 (19)
C2i—N1—C2—C5	−177.47 (8)	C5—C6—C7—C8	177.82 (12)
C1—N1—C2—C3	−176.71 (11)	C12—C7—C8—C9	−0.28 (18)
C2i—N1—C2—C3	59.97 (16)	C6—C7—C8—C9	−178.56 (11)
N1—C2—C3—C4	−56.00 (15)	C7—C8—C9—C10	0.3 (2)
C5—C2—C3—C4	−179.62 (12)	C8—C9—C10—C11	−0.1 (2)
C2—C3—C4—C3i	51.3 (2)	C9—C10—C11—C12	0.0 (2)
N1—C2—C5—C6	123.80 (14)	C10—C11—C12—C7	−0.02 (19)
C3—C2—C5—C6	−113.41 (14)	C8—C7—C12—C11	0.16 (18)
C2—C5—C6—C7	177.26 (11)	C6—C7—C12—C11	178.36 (11)