Crystal structure of 3,9,9-trimethyl-2,3,3a,4,9,9a-hexa­hydro-1H-cyclo­penta[b]quinolin-4-ium chloride

Sridhar, G.; Bilal, I.M.; Easwaramoorthy, D.; Rani, S.K.; Solomon, K.A.

doi:10.1107/S2056989015011858

organic compounds

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Volume 71| Part 7| July 2015| Pages o525-o526

doi:10.1107/S2056989015011858

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Crystal structure of 3,9,9-trimethyl-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]quinolin-4-ium chloride

G. Sridhar,^a ^* I. Mohammed Bilal,^a D. Easwaramoorthy,^a S. Kutti Rani ^a and K. Anand Solomon ^b

^aDepartment of Chemistry, B.S. Abdur Rahman University, Chennai 600 048, India, and ^bDepartment of Chemistry, Sri Sathya Sai Center for Human Excellence, Karnataka 562 101, India
^*Correspondence e-mail: sridhargopalrao@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 17 June 2015; accepted 21 June 2015; online 27 June 2015)

The title molecular salt, C₁₅H₂₂N⁺·Cl⁻, arose as an unexpected product of the reaction between aniline and melanol in the presence of HCl. The central heterocyclic ring has a half-chair conformation and the five-membered ring has an envelope conformation, with the C atom linked to the N atom as the flap. In the crystal, the ions are linked by N—H⋯Cl hydrogen bonds, generating chains propagating in the [100] direction. The crystal studied was a merohedral twin with a 0.64 (3):0.36 (3) domain ratio.

Keywords: crystal structure; quinoline; N—H⋯Cl hydrogen bonds.

CCDC reference: 1407884

1. Related literature

For biological background, see: Szymański et al. (2012 ). For further synthetic details, see: Alaghaz et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₅H₂₂N⁺·Cl⁻
M_r = 251.78
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.0291 (5) Å
b = 10.3313 (8) Å
c = 18.9425 (14) Å
V = 1375.60 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 298 K
0.35 × 0.30 × 0.30 mm

2.2. Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
7372 measured reflections
3334 independent reflections
3013 reflections with I > 2σ(I)
R_int = 0.028
Standard reflections: 0

2.3. Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.123
S = 0.95
3334 reflections
165 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack x determined using 1165 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter: 0.36 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1	1.05 (4)	2.07 (4)	3.1201 (19)	173 (3)
N1—H1B⋯Cl1ⁱ	0.93 (3)	2.17 (3)	3.0943 (19)	174 (3)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS7 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Supporting information

CCDC reference: 1407884

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015011858/hb7450sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015011858/hb7450Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015011858/hb7450Isup3.cml

checkCIF report

Introduction top

Tacrine was the drug approved by the United States Food and Drug Administration in 1993 for the palliative treatment of Alzheimer's Disease. The derivatives of the title compound, which is a congener of tacrine, has also been reported to be effective anti-alzheimeric agents (Szymanski et al., 2012). In this salt the N atom is protonated with sp3 hybridization and with a tetrahedral geometry. In the crystal, the molecules are linked via N—H···Cl bonds forming chains propagating along the a axis direction.The five membered ring adopts an envelope conformation, while the six-membered non aromatic ring adopts a twist-chair conformation as evinced from Puckering amplitude θ=46.50 (0.15), Ψ= -91.77(0.26), QT=0.5104 (1).

Experimental top

Synthesis and crystallization top

The quinoline derivative was prepared by the condensation 2,6-dimethyl-5- heptenaldehyde and aniline in 1:1 molar ratio by refluxing in propan-2-ol using HCl as a catalyst. The mixture was left under reflux for 3 h.

The solution was then left at room temperature. The solid product formed was separated by filtration, purified by crystallized with ethanol and washed with acetone and then dried in a vacuum over anhydrous calcium chloride (Alaghaz et al., 2014). The beige coloured product was formed in 80% yield.

Refinement top

The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.93 Å with Uiso(H) = 1.2Ueq(C).

Related literature top

For biological background, see: Szymański et al. (2012). For further synthetic details, see: Alaghaz et al. (2014).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS7 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP diagram of the title compound drawn at 30% probability
	Fig. 2. Packing diagram of the molecule viewed down 'b' axis

3,9,9-Trimethyl-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]quinolin-4-ium chloride top

Crystal data top

C₁₅H₂₂N⁺·Cl⁻	D_x = 1.216 Mg m⁻³
M_r = 251.78	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 25 reflections
a = 7.0291 (5) Å	θ = 2.0–25°
b = 10.3313 (8) Å	µ = 0.26 mm⁻¹
c = 18.9425 (14) Å	T = 298 K
V = 1375.60 (18) Å³	Block, colourless
Z = 4	0.35 × 0.30 × 0.30 mm
F(000) = 544

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	R_int = 0.028
ω scans	θ_max = 28.5°, θ_min = 2.2°
7372 measured reflections	h = −9→9
3334 independent reflections	k = −13→9
3013 reflections with I > 2σ(I)	l = −10→24

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.123	(Δ/σ)_max < 0.001
S = 0.95	Δρ_max = 0.26 e Å⁻³
3334 reflections	Δρ_min = −0.23 e Å⁻³
165 parameters	Absolute structure: Flack x determined using 1165 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.36 (3)

Crystal data top

C₁₅H₂₂N⁺·Cl⁻	V = 1375.60 (18) Å³
M_r = 251.78	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.0291 (5) Å	µ = 0.26 mm⁻¹
b = 10.3313 (8) Å	T = 298 K
c = 18.9425 (14) Å	0.35 × 0.30 × 0.30 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3013 reflections with I > 2σ(I)
7372 measured reflections	R_int = 0.028
3334 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.123	Δρ_max = 0.26 e Å⁻³
S = 0.95	Δρ_min = −0.23 e Å⁻³
3334 reflections	Absolute structure: Flack x determined using 1165 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
165 parameters	Absolute structure parameter: 0.36 (3)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.15461 (9)	0.64944 (6)	0.56931 (3)	0.0429 (2)
N1	0.4133 (3)	0.60045 (17)	0.43815 (9)	0.0287 (4)
C2	0.5014 (3)	0.4292 (2)	0.31431 (12)	0.0311 (5)
C3	0.6364 (3)	0.4629 (2)	0.37502 (12)	0.0306 (4)
H3	0.6958	0.5458	0.3630	0.037*
C4	0.3378 (3)	0.5258 (2)	0.31593 (10)	0.0282 (4)
C5	0.2938 (3)	0.6012 (2)	0.37467 (11)	0.0272 (4)
C6	0.5333 (3)	0.4825 (2)	0.44441 (11)	0.0284 (4)
H6	0.4519	0.4074	0.4539	0.034*
C7	0.1374 (3)	0.6827 (2)	0.37588 (13)	0.0360 (5)
H7	0.1104	0.7308	0.4162	0.043*
C8	0.0217 (3)	0.6927 (3)	0.31749 (14)	0.0409 (6)
H8	−0.0835	0.7473	0.3181	0.049*
C9	0.6887 (4)	0.4896 (2)	0.49987 (12)	0.0377 (5)
H9	0.7489	0.5750	0.4975	0.045*
C10	0.7987 (4)	0.3694 (3)	0.39459 (15)	0.0497 (7)
H10A	0.7630	0.2806	0.3844	0.060*
H10B	0.9133	0.3901	0.3684	0.060*
C11	0.2179 (3)	0.5383 (3)	0.25764 (12)	0.0375 (5)
H11	0.2427	0.4897	0.2173	0.045*
C12	0.0635 (3)	0.6210 (3)	0.25812 (14)	0.0420 (6)
H12	−0.0127	0.6283	0.2182	0.050*
C13	0.6117 (4)	0.4384 (3)	0.24472 (13)	0.0463 (6)
H13A	0.6450	0.5271	0.2359	0.070*
H13B	0.5338	0.4068	0.2068	0.070*
H13C	0.7254	0.3873	0.2479	0.070*
C14	0.6223 (4)	0.4657 (3)	0.57507 (13)	0.0518 (7)
H14A	0.5301	0.5300	0.5879	0.078*
H14B	0.7291	0.4707	0.6065	0.078*
H14C	0.5659	0.3813	0.5783	0.078*
C15	0.4183 (5)	0.2923 (2)	0.32124 (16)	0.0508 (7)
H15A	0.5201	0.2305	0.3240	0.076*
H15B	0.3407	0.2736	0.2808	0.076*
H15C	0.3423	0.2871	0.3632	0.076*
C16	0.8301 (5)	0.3879 (3)	0.47281 (15)	0.0598 (8)
H16A	0.9594	0.4165	0.4815	0.072*
H16B	0.8107	0.3066	0.4974	0.072*
H1A	0.334 (6)	0.613 (4)	0.4846 (18)	0.079 (11)*
H1B	0.490 (4)	0.673 (3)	0.4388 (16)	0.047 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0449 (3)	0.0503 (3)	0.0335 (3)	0.0088 (3)	0.0067 (2)	0.0008 (3)
N1	0.0305 (8)	0.0319 (8)	0.0238 (9)	0.0006 (7)	−0.0019 (7)	−0.0030 (7)
C2	0.0361 (10)	0.0296 (10)	0.0275 (11)	0.0002 (8)	0.0007 (8)	−0.0042 (8)
C3	0.0310 (10)	0.0334 (10)	0.0275 (11)	0.0030 (8)	0.0009 (8)	−0.0018 (8)
C4	0.0277 (9)	0.0315 (9)	0.0255 (10)	−0.0056 (9)	0.0017 (8)	−0.0010 (8)
C5	0.0273 (9)	0.0319 (9)	0.0223 (10)	−0.0029 (7)	−0.0007 (7)	0.0001 (8)
C6	0.0324 (10)	0.0280 (9)	0.0247 (10)	0.0000 (8)	−0.0022 (7)	0.0014 (8)
C7	0.0354 (11)	0.0402 (11)	0.0324 (11)	0.0052 (9)	0.0016 (9)	−0.0012 (9)
C8	0.0300 (10)	0.0514 (14)	0.0412 (14)	0.0054 (10)	−0.0023 (9)	0.0065 (11)
C9	0.0411 (12)	0.0390 (11)	0.0330 (11)	0.0053 (10)	−0.0102 (9)	−0.0005 (10)
C10	0.0461 (13)	0.0571 (16)	0.0460 (15)	0.0197 (12)	−0.0060 (11)	−0.0060 (13)
C11	0.0375 (11)	0.0471 (13)	0.0278 (11)	−0.0064 (10)	−0.0034 (9)	−0.0041 (10)
C12	0.0338 (10)	0.0564 (15)	0.0358 (12)	−0.0054 (11)	−0.0087 (9)	0.0064 (11)
C13	0.0475 (14)	0.0614 (16)	0.0301 (12)	0.0111 (12)	0.0061 (10)	−0.0058 (12)
C14	0.0647 (17)	0.0607 (16)	0.0299 (13)	0.0123 (14)	−0.0096 (12)	0.0050 (12)
C15	0.0624 (16)	0.0310 (11)	0.0591 (19)	−0.0069 (12)	−0.0096 (14)	−0.0063 (12)
C16	0.0581 (16)	0.078 (2)	0.0430 (15)	0.0322 (17)	−0.0127 (13)	−0.0071 (15)

Geometric parameters (Å, º) top

N1—C5	1.467 (3)	C9—C14	1.519 (3)
N1—C6	1.487 (3)	C9—C16	1.534 (4)
N1—H1A	1.05 (4)	C9—H9	0.9800
N1—H1B	0.93 (3)	C10—C16	1.510 (4)
C2—C4	1.523 (3)	C10—H10A	0.9700
C2—C3	1.531 (3)	C10—H10B	0.9700
C2—C13	1.532 (3)	C11—C12	1.381 (3)
C2—C15	1.536 (3)	C11—H11	0.9300
C3—C6	1.515 (3)	C12—H12	0.9300
C3—C10	1.540 (3)	C13—H13A	0.9600
C3—H3	0.9800	C13—H13B	0.9600
C4—C5	1.393 (3)	C13—H13C	0.9600
C4—C11	1.395 (3)	C14—H14A	0.9600
C5—C7	1.386 (3)	C14—H14B	0.9600
C6—C9	1.518 (3)	C14—H14C	0.9600
C6—H6	0.9800	C15—H15A	0.9600
C7—C8	1.376 (3)	C15—H15B	0.9600
C7—H7	0.9300	C15—H15C	0.9600
C8—C12	1.378 (4)	C16—H16A	0.9700
C8—H8	0.9300	C16—H16B	0.9700

C5—N1—C6	113.23 (16)	C6—C9—H9	108.8
C5—N1—H1A	112 (2)	C14—C9—H9	108.8
C6—N1—H1A	110 (2)	C16—C9—H9	108.8
C5—N1—H1B	109.9 (18)	C16—C10—C3	105.4 (2)
C6—N1—H1B	109.6 (18)	C16—C10—H10A	110.7
H1A—N1—H1B	102 (3)	C3—C10—H10A	110.7
C4—C2—C3	107.70 (17)	C16—C10—H10B	110.7
C4—C2—C13	111.01 (19)	C3—C10—H10B	110.7
C3—C2—C13	108.59 (19)	H10A—C10—H10B	108.8
C4—C2—C15	108.32 (18)	C12—C11—C4	121.8 (2)
C3—C2—C15	112.4 (2)	C12—C11—H11	119.1
C13—C2—C15	108.9 (2)	C4—C11—H11	119.1
C6—C3—C2	112.69 (18)	C8—C12—C11	120.3 (2)
C6—C3—C10	103.27 (18)	C8—C12—H12	119.8
C2—C3—C10	119.81 (19)	C11—C12—H12	119.8
C6—C3—H3	106.8	C2—C13—H13A	109.5
C2—C3—H3	106.8	C2—C13—H13B	109.5
C10—C3—H3	106.8	H13A—C13—H13B	109.5
C5—C4—C11	116.5 (2)	C2—C13—H13C	109.5
C5—C4—C2	123.37 (19)	H13A—C13—H13C	109.5
C11—C4—C2	120.08 (19)	H13B—C13—H13C	109.5
C7—C5—C4	122.0 (2)	C9—C14—H14A	109.5
C7—C5—N1	116.36 (19)	C9—C14—H14B	109.5
C4—C5—N1	121.67 (18)	H14A—C14—H14B	109.5
N1—C6—C3	108.17 (16)	C9—C14—H14C	109.5
N1—C6—C9	115.09 (18)	H14A—C14—H14C	109.5
C3—C6—C9	105.22 (18)	H14B—C14—H14C	109.5
N1—C6—H6	109.4	C2—C15—H15A	109.5
C3—C6—H6	109.4	C2—C15—H15B	109.5
C9—C6—H6	109.4	H15A—C15—H15B	109.5
C8—C7—C5	120.1 (2)	C2—C15—H15C	109.5
C8—C7—H7	120.0	H15A—C15—H15C	109.5
C5—C7—H7	120.0	H15B—C15—H15C	109.5
C7—C8—C12	119.3 (2)	C10—C16—C9	108.7 (2)
C7—C8—H8	120.3	C10—C16—H16A	110.0
C12—C8—H8	120.3	C9—C16—H16A	110.0
C6—C9—C14	114.8 (2)	C10—C16—H16B	110.0
C6—C9—C16	101.64 (19)	C9—C16—H16B	110.0
C14—C9—C16	113.6 (2)	H16A—C16—H16B	108.3

C4—C2—C3—C6	48.4 (2)	C2—C3—C6—N1	−66.8 (2)
C13—C2—C3—C6	168.67 (19)	C10—C3—C6—N1	162.49 (19)
C15—C2—C3—C6	−70.8 (2)	C2—C3—C6—C9	169.71 (19)
C4—C2—C3—C10	170.1 (2)	C10—C3—C6—C9	39.0 (2)
C13—C2—C3—C10	−69.6 (3)	C4—C5—C7—C8	−1.1 (3)
C15—C2—C3—C10	50.9 (3)	N1—C5—C7—C8	177.7 (2)
C3—C2—C4—C5	−17.9 (3)	C5—C7—C8—C12	0.0 (4)
C13—C2—C4—C5	−136.7 (2)	N1—C6—C9—C14	79.9 (3)
C15—C2—C4—C5	103.8 (2)	C3—C6—C9—C14	−161.2 (2)
C3—C2—C4—C11	164.75 (19)	N1—C6—C9—C16	−157.0 (2)
C13—C2—C4—C11	46.0 (3)	C3—C6—C9—C16	−38.0 (2)
C15—C2—C4—C11	−73.5 (3)	C6—C3—C10—C16	−23.7 (3)
C11—C4—C5—C7	1.2 (3)	C2—C3—C10—C16	−150.0 (3)
C2—C4—C5—C7	−176.2 (2)	C5—C4—C11—C12	−0.1 (3)
C11—C4—C5—N1	−177.55 (19)	C2—C4—C11—C12	177.3 (2)
C2—C4—C5—N1	5.1 (3)	C7—C8—C12—C11	1.1 (4)
C6—N1—C5—C7	159.69 (19)	C4—C11—C12—C8	−1.0 (4)
C6—N1—C5—C4	−21.5 (3)	C3—C10—C16—C9	0.4 (3)
C5—N1—C6—C3	50.1 (2)	C6—C9—C16—C10	22.9 (3)
C5—N1—C6—C9	167.43 (18)	C14—C9—C16—C10	146.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	1.05 (4)	2.07 (4)	3.1201 (19)	173 (3)
N1—H1B···Cl1ⁱ	0.93 (3)	2.17 (3)	3.0943 (19)	174 (3)

Symmetry code: (i) x+1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	1.05 (4)	2.07 (4)	3.1201 (19)	173 (3)
N1—H1B···Cl1ⁱ	0.93 (3)	2.17 (3)	3.0943 (19)	174 (3)

Symmetry code: (i) x+1/2, −y+3/2, −z+1.

Acknowledgements

SG acknowledges Dr Sriman Narayanan, Professor & Head, Department of Analytical Chemistry, University of Madras, for fruitful discussions.

References

Alaghaz, A. M. A., Ammar, Y. A., Bayoumi, H. A. & Aldhlmani, S. A. (2014). J. Mol. Struct. 1074, 359–375. CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Szymański, P., Lázničková, A., Lázniček, M., Bajda, M., Malawska, B., Markowicz, M. & Mikiciuk-Olasik, E. (2012). Int. J. Mol. Sci. 13, 10067–10090. PubMed Google Scholar

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o525-o526

doi:10.1107/S2056989015011858

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 3,9,9-tri­methyl-2,3,3a,4,9,9a-hexa­hydro-1H-cyclo­penta[b]quinolin-4-ium chloride

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 3,9,9-trimethyl-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]quinolin-4-ium chloride