(2S,6S)-1-Methyl-2,6-trans-distyryl-piperidinium chloride.

In the crystal structure of the title compound, C(22)H(26)N(+)·Cl(-), the piperidine ring is in a chair conformation and the two styryl groups are in axial and equatorial positions. The mol-ecule has a hydrogen bond between the NH group and the chloride anion.

Related literature

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

Experimental

Crystal data

C22H26N+·Cl−

M = 339.89

Orthorhombic,

a = 9.9355 (4) Å

b = 12.3075 (5) Å

c = 15.8299 (7) Å

V = 1935.70 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.38 × 0.28 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.930, T max = 0.984

11921 measured reflections

3416 independent reflections

2957 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.091

S = 1.11

3416 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 1457 Friedel pairs

Flack parameter: 0.06 (7)

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 Siemens SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049587/hg2599sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049587/hg2599Isup2.hkl

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

C22H26N+·Cl−	F(000) = 728
Mr = 339.89	Dx = 1.166 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 21849 reflections
a = 9.9355 (4) Å	θ = 1.0–27.5°
b = 12.3075 (5) Å	µ = 0.20 mm−1
c = 15.8299 (7) Å	T = 173 K
V = 1935.70 (14) Å3	Irregular plates, colourless
Z = 4	0.38 × 0.28 × 0.08 mm

Nonius KappaCCD diffractometer	3416 independent reflections
Radiation source: fine-focus sealed tube	2957 reflections with I > 2σ(I)
graphite	Rint = 0.065
Detector resolution: 18 pixels mm-1	θmax = 25.0°, θmin = 2.1°
ω scans at fixed χ = 55°	h = −11→11
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −14→14
Tmin = 0.930, Tmax = 0.984	l = −18→18
11921 measured 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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0332P)2 + 0.1721P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
3416 reflections	Δρmax = 0.45 e Å−3
218 parameters	Δρmin = −0.26 e Å−3
0 restraints	Absolute structure: Flack (1983), 1457 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (7)

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
Cl	0.49125 (6)	1.13417 (4)	0.35616 (4)	0.03556 (19)
N1	0.44499 (17)	0.82481 (15)	0.25784 (13)	0.0275 (5)
H1	0.4661	0.7643	0.2253	0.033*
C1	0.4017 (3)	0.9121 (2)	0.19752 (16)	0.0358 (7)
H1A	0.3144	0.8928	0.1729	0.054*
H1B	0.4687	0.9192	0.1524	0.054*
H1C	0.3938	0.9812	0.2278	0.054*
C2	0.3304 (2)	0.79138 (19)	0.31510 (17)	0.0305 (6)
H2	0.2579	0.7607	0.2783	0.037*
C3	0.3774 (3)	0.7007 (2)	0.37336 (17)	0.0372 (7)
H3A	0.3035	0.6812	0.4125	0.045*
H3B	0.3991	0.6356	0.3392	0.045*
C4	0.5004 (3)	0.7336 (2)	0.42414 (16)	0.0395 (7)
H4A	0.4780	0.7958	0.4612	0.047*
H4B	0.5298	0.6724	0.4602	0.047*
C5	0.6127 (2)	0.76520 (19)	0.36400 (16)	0.0331 (6)
H5A	0.6390	0.7008	0.3304	0.040*
H5B	0.6920	0.7884	0.3972	0.040*
C6	0.5726 (2)	0.85631 (19)	0.30435 (15)	0.0272 (6)
H6	0.5545	0.9232	0.3383	0.033*
C7	0.6841 (2)	0.87992 (19)	0.24306 (15)	0.0292 (6)
H7	0.7039	0.8283	0.2002	0.035*
C8	0.7558 (2)	0.9709 (2)	0.24688 (15)	0.0283 (6)
H8	0.7260	1.0241	0.2861	0.034*
C9	0.8759 (2)	0.9986 (2)	0.19738 (15)	0.0281 (6)
C10	0.9516 (2)	1.0897 (2)	0.22012 (17)	0.0342 (7)
H10	0.9237	1.1327	0.2667	0.041*
C11	1.0659 (2)	1.1182 (2)	0.17623 (18)	0.0391 (7)
H11	1.1164	1.1800	0.1932	0.047*
C12	1.1074 (3)	1.0578 (2)	0.10788 (17)	0.0444 (8)
H12	1.1859	1.0780	0.0775	0.053*
C13	1.0347 (3)	0.9682 (2)	0.08396 (17)	0.0460 (8)
H13	1.0629	0.9266	0.0366	0.055*
C14	0.9202 (3)	0.9378 (2)	0.12838 (17)	0.0419 (7)
H14	0.8715	0.8750	0.1116	0.050*
C15	0.2714 (2)	0.88730 (18)	0.36100 (16)	0.0278 (6)
H15	0.3300	0.9378	0.3875	0.033*
C16	0.1402 (2)	0.90289 (19)	0.36523 (17)	0.0307 (6)
H16	0.0856	0.8520	0.3359	0.037*
C17	0.0685 (2)	0.9906 (2)	0.41046 (14)	0.0257 (6)
C18	−0.0696 (2)	0.9803 (2)	0.42416 (15)	0.0312 (6)
H18	−0.1147	0.9167	0.4054	0.037*
C19	−0.1417 (3)	1.0608 (2)	0.46452 (16)	0.0383 (7)
H19	−0.2359	1.0527	0.4729	0.046*
C20	−0.0774 (3)	1.1519 (2)	0.49227 (17)	0.0390 (7)
H20	−0.1269	1.2071	0.5204	0.047*
C21	0.0595 (3)	1.1644 (2)	0.47978 (16)	0.0342 (7)
H21	0.1037	1.2278	0.4998	0.041*
C22	0.1322 (3)	1.0848 (2)	0.43814 (15)	0.0290 (6)
H22	0.2258	1.0945	0.4284	0.035*

	U11	U22	U33	U12	U13	U23
Cl	0.0428 (4)	0.0231 (3)	0.0408 (4)	−0.0033 (3)	0.0079 (3)	−0.0019 (3)
N1	0.0250 (11)	0.0208 (11)	0.0369 (12)	0.0017 (9)	0.0023 (10)	−0.0077 (10)
C1	0.0337 (16)	0.0357 (15)	0.0379 (16)	0.0067 (13)	−0.0034 (13)	−0.0001 (14)
C2	0.0190 (14)	0.0247 (14)	0.0478 (16)	−0.0070 (11)	0.0024 (13)	−0.0055 (13)
C3	0.0334 (16)	0.0283 (15)	0.0500 (18)	−0.0045 (12)	0.0089 (14)	0.0034 (14)
C4	0.0414 (16)	0.0329 (14)	0.0442 (17)	0.0019 (15)	0.0055 (16)	0.0147 (13)
C5	0.0243 (14)	0.0306 (15)	0.0445 (17)	0.0002 (12)	−0.0047 (13)	0.0062 (14)
C6	0.0194 (13)	0.0244 (14)	0.0377 (15)	−0.0057 (12)	−0.0040 (12)	−0.0056 (13)
C7	0.0256 (13)	0.0319 (15)	0.0301 (15)	0.0050 (13)	−0.0009 (12)	−0.0023 (13)
C8	0.0236 (14)	0.0294 (15)	0.0319 (15)	0.0007 (12)	−0.0023 (12)	−0.0012 (13)
C9	0.0218 (14)	0.0360 (16)	0.0264 (14)	0.0004 (12)	−0.0029 (12)	0.0050 (13)
C10	0.0288 (15)	0.0325 (15)	0.0412 (16)	0.0026 (12)	−0.0026 (13)	0.0033 (13)
C11	0.0294 (15)	0.0356 (17)	0.0523 (19)	−0.0086 (13)	−0.0001 (14)	0.0098 (16)
C12	0.0300 (16)	0.061 (2)	0.0427 (18)	−0.0069 (16)	0.0042 (14)	0.0142 (16)
C13	0.0379 (18)	0.066 (2)	0.0339 (17)	−0.0039 (16)	0.0074 (14)	−0.0072 (15)
C14	0.0347 (16)	0.0530 (18)	0.0380 (18)	−0.0100 (14)	−0.0044 (14)	−0.0036 (16)
C15	0.0241 (14)	0.0235 (14)	0.0359 (15)	−0.0025 (11)	0.0007 (12)	−0.0038 (12)
C16	0.0280 (15)	0.0262 (14)	0.0379 (15)	−0.0046 (11)	−0.0065 (13)	−0.0035 (13)
C17	0.0231 (14)	0.0276 (15)	0.0265 (14)	0.0052 (12)	−0.0040 (11)	0.0030 (12)
C18	0.0238 (15)	0.0347 (16)	0.0350 (15)	−0.0033 (13)	−0.0051 (12)	−0.0003 (13)
C19	0.0237 (15)	0.0502 (19)	0.0410 (18)	0.0055 (14)	0.0035 (13)	−0.0038 (15)
C20	0.0382 (18)	0.0449 (19)	0.0338 (16)	0.0115 (15)	0.0034 (13)	−0.0065 (15)
C21	0.0378 (17)	0.0297 (17)	0.0352 (16)	−0.0010 (13)	0.0011 (13)	−0.0052 (13)
C22	0.0224 (14)	0.0335 (15)	0.0311 (15)	−0.0016 (12)	0.0019 (12)	0.0009 (13)

N1—C1	1.500 (3)	C9—C10	1.397 (3)
N1—C2	1.512 (3)	C10—C11	1.377 (3)
N1—C6	1.517 (3)	C10—H10	0.9500
N1—H1	0.9300	C11—C12	1.376 (3)
C1—H1A	0.9800	C11—H11	0.9500
C1—H1B	0.9800	C12—C13	1.371 (4)
C1—H1C	0.9800	C12—H12	0.9500
C2—C15	1.505 (3)	C13—C14	1.389 (3)
C2—C3	1.522 (3)	C13—H13	0.9500
C2—H2	1.0000	C14—H14	0.9500
C3—C4	1.518 (3)	C15—C16	1.320 (3)
C3—H3A	0.9900	C15—H15	0.9500
C3—H3B	0.9900	C16—C17	1.478 (3)
C4—C5	1.517 (3)	C16—H16	0.9500
C4—H4A	0.9900	C17—C22	1.392 (3)
C4—H4B	0.9900	C17—C18	1.394 (3)
C5—C6	1.519 (3)	C18—C19	1.380 (3)
C5—H5A	0.9900	C18—H18	0.9500
C5—H5B	0.9900	C19—C20	1.363 (4)
C6—C7	1.501 (3)	C19—H19	0.9500
C6—H6	1.0000	C20—C21	1.383 (3)
C7—C8	1.329 (3)	C20—H20	0.9500
C7—H7	0.9500	C21—C22	1.384 (3)
C8—C9	1.468 (3)	C21—H21	0.9500
C8—H8	0.9500	C22—H22	0.9500
C9—C14	1.395 (3)
C1—N1—C2	111.13 (18)	C7—C8—C9	127.4 (2)
C1—N1—C6	111.45 (18)	C7—C8—H8	116.3
C2—N1—C6	114.09 (19)	C9—C8—H8	116.3
C1—N1—H1	106.5	C14—C9—C10	117.5 (2)
C2—N1—H1	106.5	C14—C9—C8	123.4 (2)
C6—N1—H1	106.5	C10—C9—C8	119.1 (2)
N1—C1—H1A	109.5	C11—C10—C9	121.2 (3)
N1—C1—H1B	109.5	C11—C10—H10	119.4
H1A—C1—H1B	109.5	C9—C10—H10	119.4
N1—C1—H1C	109.5	C12—C11—C10	120.4 (3)
H1A—C1—H1C	109.5	C12—C11—H11	119.8
H1B—C1—H1C	109.5	C10—C11—H11	119.8
C15—C2—N1	111.67 (18)	C13—C12—C11	119.6 (3)
C15—C2—C3	113.7 (2)	C13—C12—H12	120.2
N1—C2—C3	109.39 (19)	C11—C12—H12	120.2
C15—C2—H2	107.2	C12—C13—C14	120.6 (3)
N1—C2—H2	107.2	C12—C13—H13	119.7
C3—C2—H2	107.2	C14—C13—H13	119.7
C4—C3—C2	111.81 (19)	C13—C14—C9	120.7 (3)
C4—C3—H3A	109.3	C13—C14—H14	119.7
C2—C3—H3A	109.3	C9—C14—H14	119.7
C4—C3—H3B	109.3	C16—C15—C2	121.6 (2)
C2—C3—H3B	109.3	C16—C15—H15	119.2
H3A—C3—H3B	107.9	C2—C15—H15	119.2
C5—C4—C3	109.2 (2)	C15—C16—C17	127.4 (2)
C5—C4—H4A	109.8	C15—C16—H16	116.3
C3—C4—H4A	109.8	C17—C16—H16	116.3
C5—C4—H4B	109.8	C22—C17—C18	118.3 (2)
C3—C4—H4B	109.8	C22—C17—C16	122.8 (2)
H4A—C4—H4B	108.3	C18—C17—C16	118.9 (2)
C4—C5—C6	112.74 (19)	C19—C18—C17	121.2 (3)
C4—C5—H5A	109.0	C19—C18—H18	119.4
C6—C5—H5A	109.0	C17—C18—H18	119.4
C4—C5—H5B	109.0	C20—C19—C18	119.7 (2)
C6—C5—H5B	109.0	C20—C19—H19	120.1
H5A—C5—H5B	107.8	C18—C19—H19	120.1
C7—C6—N1	110.65 (18)	C19—C20—C21	120.5 (3)
C7—C6—C5	110.60 (19)	C19—C20—H20	119.8
N1—C6—C5	109.39 (19)	C21—C20—H20	119.8
C7—C6—H6	108.7	C20—C21—C22	120.2 (3)
N1—C6—H6	108.7	C20—C21—H21	119.9
C5—C6—H6	108.7	C22—C21—H21	119.9
C8—C7—C6	122.0 (2)	C21—C22—C17	120.1 (2)
C8—C7—H7	119.0	C21—C22—H22	119.9
C6—C7—H7	119.0	C17—C22—H22	119.9
C1—N1—C2—C15	−54.9 (3)	C8—C9—C10—C11	179.3 (2)
C6—N1—C2—C15	72.2 (2)	C9—C10—C11—C12	0.7 (4)
C1—N1—C2—C3	178.35 (18)	C10—C11—C12—C13	−0.4 (4)
C6—N1—C2—C3	−54.6 (3)	C11—C12—C13—C14	−0.4 (4)
C15—C2—C3—C4	−69.2 (3)	C12—C13—C14—C9	0.9 (4)
N1—C2—C3—C4	56.4 (3)	C10—C9—C14—C13	−0.6 (4)
C2—C3—C4—C5	−58.0 (3)	C8—C9—C14—C13	180.0 (2)
C3—C4—C5—C6	57.4 (3)	N1—C2—C15—C16	133.2 (3)
C1—N1—C6—C7	−57.5 (2)	C3—C2—C15—C16	−102.5 (3)
C2—N1—C6—C7	175.62 (18)	C2—C15—C16—C17	177.6 (2)
C1—N1—C6—C5	−179.60 (19)	C15—C16—C17—C22	16.4 (4)
C2—N1—C6—C5	53.5 (2)	C15—C16—C17—C18	−165.4 (3)
C4—C5—C6—C7	−176.7 (2)	C22—C17—C18—C19	−0.4 (4)
C4—C5—C6—N1	−54.6 (3)	C16—C17—C18—C19	−178.7 (2)
N1—C6—C7—C8	129.0 (2)	C17—C18—C19—C20	−0.5 (4)
C5—C6—C7—C8	−109.6 (3)	C18—C19—C20—C21	0.4 (4)
C6—C7—C8—C9	172.7 (2)	C19—C20—C21—C22	0.6 (4)
C7—C8—C9—C14	10.4 (4)	C20—C21—C22—C17	−1.5 (4)
C7—C8—C9—C10	−169.0 (2)	C18—C17—C22—C21	1.4 (4)
C14—C9—C10—C11	−0.2 (3)	C16—C17—C22—C21	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cli	0.93	2.10	3.027 (2)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cli	0.93	2.10	3.027 (2)	176

Symmetry code: (i) .