2-(Cyclo­hexa-1,4-dien­yl)-2-(4-methoxy­phen­yl)-N,N-dimethyl­ethanaminium chloride

Lou, W.-J.; Hu, X.-R.

doi:10.1107/S1600536809027627

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1916

doi:10.1107/S1600536809027627

Open

access

2-(Cyclohexa-1,4-dienyl)-2-(4-methoxyphenyl)-N,N-dimethylethanaminium chloride

Wei-Jian Lou ^a and Xiu-Rong Hu ^b ^*

^aDepartment of Pharmacy, Sir Run Shaw Institute of Clinical Medicine, Zhejiang University, Hangzhou, Zhejiang 310016, People's Republic of China, and ^bCenter for Analysis and Measurement, Zhejiang University, Hangzhou, Zhejiang 310028, People's Republic of China
^*Correspondence e-mail: huxiurong@yahoo.com.cn

(Received 26 June 2009; accepted 14 July 2009; online 18 July 2009)

In the title compound, C₁₇H₂₄NO⁺·Cl⁻, the cyclohexa-1,4-diene ring, which is almost planar, with a maximum deviation of 0.024 (4) Å from the mean plane, makes a dihedral angle of 66.4 (1)° with the benzene ring. In the crystal, intermolecular N—H⋯Cl and C—H⋯Cl hydrogen bonds link the molecules into an infinite chain along the b axis.

Related literature

The title compound is an impurity that is sometimes yielded during the preparation of venlafaxine, one of a novel group of antidepressants characterized by their ability to selectively inhibit the pro-synaptic re-uptake of both serotonin and noradrenaline, see: Vega et al. (2000 ); Yardley et al. (1990 ).

Experimental

Crystal data

C₁₇H₂₄NO⁺·Cl⁻
M_r = 293.84
Orthorhombic, P b c a
a = 11.1245 (7) Å
b = 10.9248 (6) Å
c = 28.9651 (16) Å
V = 3520.2 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.32 × 0.28 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.927, T_max = 0.979
32170 measured reflections
4010 independent reflections
2102 reflections with F² > 2σ(F²)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.140
S = 1.00
4010 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H101⋯Cl1	0.86	2.28	3.033 (2)	146
C17—H173⋯Cl1ⁱ	0.96	2.75	3.641 (3)	155
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ), and Larson (1970 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027627/is2435sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027627/is2435Isup2.hkl

checkCIF report

Comment top

The title compound is impurity of venlafaxine, which is a presentative of a novel group of antidepressants and is characterized by its ability to inhibit selectively the presynaptic reuptake of both serotonin and noradrenaline (Vega et al., 2009; Yardley et al., 1990). The asymmetric unit of the title compound contains a C₁₇H₂₄NO⁺ cation and a Cl^- anion. The ethylammonium N atom, N1, shows quatarnary character due to proton transfer from HCl and consequently bears the positive charge in the molecular cation. The N1 bond angles range from 108 to 115°, confirming the tetrahedral bond configuration, which is similar to that of venlafaxine hydrochloride (Vega et al., 2009). An intermolecular hydrogen bond N1—H101···Cl1 is formed between atom Cl and atom N of ethylammonium. This hydrogen bond and a weak intermolecular interaction C17—H173···Cl1ⁱ [symmetry code: (i) 1/2 - x, 1/2 + y, z)] link the molecules into a chain along the b axis (Fig. 2). Crystal packing is stabilized by these hydrogen-bond interactions and intermolecular interactions. In the crystal structure of the title compound, the cyclohexa-1,4-diene ring C2–C7 is almost planar, with a maximum deviation of 0.024 (4) Å at C4, which is revealed by torsion angle C2—C3—C4—C5 of -3.6 (6)° and C5—C6—C7—C2 of 0.5 (8)°. This cyclohexadiene plane forms dihedral angle of 66.4 (1)° with the benzene C8–C13 ring plane.

Related literature top

The title compound is impurity of venlafaxine, one of a novel group of antidepressants characterized by their ability to inhibit selectively the presynaptic reuptake of both serotonin and noradrenaline, see: Vega et al. (2000); Yardley et al. (1990).

Experimental top

The crude product is supplied by Zhejiang Menovo Pharmaceutical Co., LTD. It was recrystallized from an ethanol solution, giving colorless crystals of (1) suitable for X-ray diffraction.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004) and Larson (1970); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Figures top

	Fig. 1. A view of (1). Displacement ellipsoids are drawn at 40% probability level and H atoms are shown as small circles of arbitrary radii.
	Fig. 2. A chain of molecules in (1). Displacement ellipsoids are drawn at the 30% probability level and molecular interactions are shown in dashed lines [symmetry code: (i) 1/2 - x, 1/2 + y, z); (ii) 1/2 - x, -1/2 + y,z].

2-(Cyclohexa-1,4-dienyl)-2-(4-methoxyphenyl)-N,N-dimethylethanaminium chloride top

Crystal data top

C₁₇H₂₄NO⁺·Cl⁻	F(000) = 1264.00
M_r = 293.84	D_x = 1.109 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 14141 reflections
a = 11.1245 (7) Å	θ = 3.4–27.4°
b = 10.9248 (6) Å	µ = 0.21 mm⁻¹
c = 28.9651 (16) Å	T = 296 K
V = 3520.2 (4) Å³	Chunk, colorless
Z = 8	0.32 × 0.28 × 0.10 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2102 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.081
ω scans	θ_max = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
T_min = 0.927, T_max = 0.979	k = −14→14
32170 measured reflections	l = −37→37
4010 independent reflections

Refinement top

Refinement on F²	w = 1/[0.0003F_o² + 1.2σ(F_o²)]/(4F_o²)
R[F² > 2σ(F²)] = 0.060	(Δ/σ)_max < 0.001
wR(F²) = 0.140	Δρ_max = 0.61 e Å⁻³
S = 1.00	Δρ_min = −0.46 e Å⁻³
4010 reflections	Extinction correction: Larson (1970)
182 parameters	Extinction coefficient: 41 (8)
H-atom parameters constrained

Crystal data top

C₁₇H₂₄NO⁺·Cl⁻	V = 3520.2 (4) Å³
M_r = 293.84	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.1245 (7) Å	µ = 0.21 mm⁻¹
b = 10.9248 (6) Å	T = 296 K
c = 28.9651 (16) Å	0.32 × 0.28 × 0.10 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4010 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2102 reflections with F² > 2σ(F²)
T_min = 0.927, T_max = 0.979	R_int = 0.081
32170 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	182 parameters
wR(F²) = 0.140	H-atom parameters constrained
S = 1.00	Δρ_max = 0.61 e Å⁻³
4010 reflections	Δρ_min = −0.46 e Å⁻³

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
Cl1	0.42790 (7)	0.47986 (7)	0.74727 (3)	0.0737 (2)
O1	0.4316 (3)	1.1886 (2)	0.52350 (11)	0.1084 (15)
N1	0.3030 (2)	0.7155 (2)	0.71965 (8)	0.0560 (8)
C1	0.3672 (4)	0.7774 (3)	0.63900 (12)	0.0798 (15)
C2	0.4533 (3)	0.6719 (3)	0.63249 (10)	0.0648 (12)
C3	0.4132 (3)	0.5682 (3)	0.61543 (14)	0.1020 (16)
C4	0.4901 (5)	0.4576 (3)	0.60790 (19)	0.107 (2)
C5	0.6194 (5)	0.4795 (5)	0.6190 (2)	0.116 (3)
C6	0.6589 (4)	0.5804 (5)	0.6361 (2)	0.113 (2)
C7	0.5830 (3)	0.6861 (3)	0.64451 (12)	0.0966 (16)
C8	0.3907 (3)	0.8877 (3)	0.60874 (12)	0.0673 (12)
C9	0.3342 (3)	0.8903 (3)	0.56642 (14)	0.0884 (14)
C10	0.3462 (4)	0.9886 (4)	0.53674 (14)	0.1093 (18)
C11	0.4152 (5)	1.0848 (4)	0.54957 (16)	0.1011 (18)
C12	0.4754 (3)	1.0832 (3)	0.59101 (16)	0.0911 (15)
C13	0.4636 (3)	0.9849 (3)	0.62048 (12)	0.0743 (13)
C14	0.3725 (6)	1.1963 (5)	0.48060 (16)	0.111 (3)
C15	0.3360 (3)	0.8142 (3)	0.68660 (11)	0.0880 (15)
C16	0.1802 (2)	0.6651 (2)	0.71478 (12)	0.0803 (13)
C17	0.3200 (3)	0.7682 (2)	0.76629 (10)	0.0716 (11)
H1	0.2912	0.7452	0.6269	0.096*
H3	0.3322	0.5632	0.6076	0.122*
H5	0.6741	0.4170	0.6133	0.139*
H6	0.7401	0.5859	0.6434	0.136*
H9	0.2867	0.8243	0.5576	0.106*
H10	0.3074	0.9886	0.5083	0.131*
H12	0.5244	1.1487	0.5992	0.109*
H13	0.5048	0.9841	0.6484	0.089*
H41	0.4606	0.3919	0.6274	0.129*
H42	0.4839	0.4334	0.5758	0.129*
H71	0.5880	0.7057	0.6771	0.116*
H72	0.6147	0.7538	0.6266	0.116*
H101	0.3533	0.6564	0.7163	0.067*
H141	0.4108	1.1424	0.4589	0.133*
H142	0.3766	1.2789	0.4694	0.133*
H143	0.2899	1.1728	0.4843	0.133*
H151	0.2683	0.8699	0.6847	0.106*
H152	0.4049	0.8569	0.6993	0.106*
H161	0.1657	0.6066	0.7389	0.096*
H162	0.1726	0.6256	0.6853	0.096*
H163	0.1227	0.7303	0.7170	0.096*
H171	0.3986	0.8040	0.7684	0.086*
H172	0.3122	0.7047	0.7890	0.086*
H173	0.2603	0.8299	0.7717	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0623 (5)	0.0523 (4)	0.1064 (6)	0.0042 (4)	−0.0143 (5)	0.0124 (5)
O1	0.131 (4)	0.092 (2)	0.103 (2)	0.038 (2)	0.040 (2)	0.0221 (18)
N1	0.0502 (18)	0.0466 (15)	0.0711 (17)	0.0117 (13)	0.0113 (14)	0.0100 (14)
C1	0.104 (4)	0.053 (2)	0.082 (2)	0.022 (2)	0.022 (2)	0.011 (2)
C2	0.077 (2)	0.054 (2)	0.063 (2)	0.012 (2)	0.007 (2)	0.0001 (17)
C3	0.086 (3)	0.061 (2)	0.158 (3)	0.008 (2)	−0.018 (2)	−0.036 (2)
C4	0.123 (5)	0.065 (3)	0.134 (5)	0.000 (3)	0.001 (4)	−0.009 (3)
C5	0.116 (5)	0.102 (6)	0.129 (8)	0.013 (4)	−0.003 (5)	−0.003 (5)
C6	0.099 (4)	0.108 (5)	0.134 (7)	0.011 (4)	−0.005 (4)	−0.009 (5)
C7	0.101 (3)	0.104 (3)	0.085 (2)	−0.004 (2)	−0.017 (2)	−0.013 (2)
C8	0.089 (2)	0.050 (2)	0.063 (2)	0.017 (2)	0.020 (2)	0.0053 (18)
C9	0.112 (3)	0.082 (2)	0.071 (2)	0.000 (2)	0.005 (2)	−0.012 (2)
C10	0.155 (4)	0.111 (3)	0.062 (2)	0.047 (3)	0.008 (2)	0.004 (2)
C11	0.162 (5)	0.063 (2)	0.078 (3)	0.036 (3)	0.050 (3)	0.020 (2)
C12	0.125 (3)	0.061 (2)	0.088 (2)	−0.005 (2)	0.031 (2)	−0.007 (2)
C13	0.099 (3)	0.058 (2)	0.066 (2)	0.010 (2)	0.015 (2)	0.002 (2)
C14	0.133 (9)	0.105 (6)	0.095 (3)	0.036 (6)	0.035 (4)	0.036 (3)
C15	0.109 (3)	0.071 (2)	0.084 (2)	0.026 (2)	0.032 (2)	0.029 (2)
C16	0.050 (2)	0.067 (2)	0.124 (3)	−0.004 (2)	−0.016 (2)	−0.010 (2)
C17	0.068 (2)	0.069 (2)	0.077 (2)	−0.000 (2)	−0.0014 (18)	−0.0100 (18)

Geometric parameters (Å, º) top

O1—C11	1.374 (5)	C3—H3	0.930
O1—C14	1.408 (6)	C4—H41	0.970
N1—C15	1.488 (4)	C4—H42	0.970
N1—C16	1.479 (4)	C5—H5	0.930
N1—C17	1.481 (3)	C6—H6	0.930
C1—C2	1.511 (5)	C7—H71	0.970
C1—C8	1.513 (4)	C7—H72	0.970
C1—C15	1.478 (4)	C9—H9	0.930
C2—C3	1.315 (5)	C10—H10	0.930
C2—C7	1.492 (4)	C12—H12	0.930
C3—C4	1.496 (6)	C13—H13	0.930
C4—C5	1.493 (8)	C14—H141	0.960
C5—C6	1.286 (8)	C14—H142	0.960
C6—C7	1.451 (6)	C14—H143	0.960
C8—C9	1.378 (5)	C15—H151	0.970
C8—C13	1.378 (5)	C15—H152	0.970
C9—C10	1.381 (6)	C16—H161	0.960
C10—C11	1.354 (7)	C16—H162	0.960
C11—C12	1.375 (6)	C16—H163	0.960
C12—C13	1.379 (5)	C17—H171	0.960
N1—H101	0.860	C17—H172	0.960
C1—H1	0.980	C17—H173	0.960

C11—O1—C14	118.2 (3)	C6—C5—H5	118.3
C15—N1—C16	115.9 (2)	C5—C6—H6	118.4
C15—N1—C17	105.9 (2)	C7—C6—H6	118.4
C16—N1—C17	110.5 (2)	C2—C7—H71	107.8
C2—C1—C8	115.2 (3)	C2—C7—H72	107.8
C2—C1—C15	118.2 (2)	C6—C7—H71	107.8
C8—C1—C15	111.4 (2)	C6—C7—H72	107.8
C1—C2—C3	119.3 (3)	H71—C7—H72	109.5
C1—C2—C7	120.3 (3)	C8—C9—H9	119.1
C3—C2—C7	120.4 (3)	C10—C9—H9	119.1
C2—C3—C4	123.8 (4)	C9—C10—H10	120.4
C3—C4—C5	113.0 (4)	C11—C10—H10	120.4
C4—C5—C6	123.3 (5)	C11—C12—H12	119.9
C5—C6—C7	123.3 (5)	C13—C12—H12	119.9
C2—C7—C6	116.1 (3)	C8—C13—H13	119.9
C1—C8—C9	116.9 (3)	C12—C13—H13	119.9
C1—C8—C13	124.9 (3)	O1—C14—H141	109.5
C9—C8—C13	118.1 (3)	O1—C14—H142	109.5
C8—C9—C10	121.7 (3)	O1—C14—H143	109.5
C9—C10—C11	119.2 (4)	H141—C14—H142	109.5
O1—C11—C10	124.4 (4)	H141—C14—H143	109.5
O1—C11—C12	115.2 (4)	H142—C14—H143	109.5
C10—C11—C12	120.4 (4)	N1—C15—H151	107.4
C11—C12—C13	120.3 (3)	N1—C15—H152	107.4
C8—C13—C12	120.3 (3)	C1—C15—H151	107.4
N1—C15—C1	117.4 (2)	C1—C15—H152	107.4
C15—N1—H101	108.1	H151—C15—H152	109.5
C16—N1—H101	108.1	N1—C16—H161	109.5
C17—N1—H101	108.1	N1—C16—H162	109.5
C2—C1—H1	103.2	N1—C16—H163	109.5
C8—C1—H1	103.2	H161—C16—H162	109.5
C15—C1—H1	103.2	H161—C16—H163	109.5
C2—C3—H3	118.1	H162—C16—H163	109.5
C4—C3—H3	118.1	N1—C17—H171	109.5
C3—C4—H41	108.6	N1—C17—H172	109.5
C3—C4—H42	108.6	N1—C17—H173	109.5
C5—C4—H41	108.6	H171—C17—H172	109.5
C5—C4—H42	108.6	H171—C17—H173	109.5
H41—C4—H42	109.5	H172—C17—H173	109.5
C4—C5—H5	118.3

C14—O1—C11—C10	0.3 (6)	C3—C2—C7—C6	0.2 (3)
C14—O1—C11—C12	180.0 (4)	C7—C2—C3—C4	1.6 (5)
C16—N1—C15—C1	−77.4 (4)	C2—C3—C4—C5	−3.6 (6)
C17—N1—C15—C1	159.8 (3)	C3—C4—C5—C6	4.3 (8)
C2—C1—C8—C9	90.1 (4)	C4—C5—C6—C7	−2.9 (10)
C2—C1—C8—C13	−90.2 (4)	C5—C6—C7—C2	0.5 (8)
C8—C1—C2—C3	−113.9 (3)	C1—C8—C9—C10	177.8 (3)
C8—C1—C2—C7	65.0 (4)	C1—C8—C13—C12	−177.6 (3)
C2—C1—C15—N1	−46.9 (5)	C9—C8—C13—C12	2.1 (5)
C15—C1—C2—C3	110.9 (4)	C13—C8—C9—C10	−1.9 (6)
C15—C1—C2—C7	−70.2 (4)	C8—C9—C10—C11	−0.1 (5)
C8—C1—C15—N1	176.3 (3)	C9—C10—C11—O1	−178.4 (4)
C15—C1—C8—C9	−131.7 (3)	C9—C10—C11—C12	1.9 (7)
C15—C1—C8—C13	48.0 (5)	O1—C11—C12—C13	178.6 (4)
C1—C2—C3—C4	−179.5 (3)	C10—C11—C12—C13	−1.7 (7)
C1—C2—C7—C6	−178.7 (3)	C11—C12—C13—C8	−0.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H101···Cl1	0.86	2.28	3.033 (2)	146
C17—H173···Cl1ⁱ	0.96	2.75	3.641 (3)	155

Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₄NO⁺·Cl⁻
M_r	293.84
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	11.1245 (7), 10.9248 (6), 28.9651 (16)
V (Å³)	3520.2 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.32 × 0.28 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.927, 0.979
No. of measured, independent and observed [F² > 2σ(F²)] reflections	32170, 4010, 2102
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.140, 1.00
No. of reflections	4010
No. of parameters	182
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.46

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004) and Larson (1970), SIR97 (Altomare et al., 1999), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997), CrystalStructure (Rigaku/MSC, 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H101···Cl1	0.86	2.28	3.033 (2)	146
C17—H173···Cl1ⁱ	0.96	2.75	3.641 (3)	155

Symmetry code: (i) −x+1/2, y+1/2, z.

Acknowledgements

This project was supported by the Zhejiang Provincial Natural Science Foundation of China.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard. Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Vega, D., Fernández, D. & Echeverría, G. (2000). Acta Cryst. C56, 1009–1010. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Yardley, J. P., Husbands, G. E. G., Stack, G., Butch, J., Bicksler, J., Moyer, J. A., Muth, E. A., Andree, T., Fletcher, H., James, M. N. G. & Sielecki, A. R. (1990). J. Med. Chem. 33, 2899–2905. CSD CrossRef PubMed CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1916

doi:10.1107/S1600536809027627

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

2-(Cyclo­hexa-1,4-dien­yl)-2-(4-meth­oxy­phen­yl)-N,N-di­methyl­ethanaminium chloride

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-(Cyclohexa-1,4-dienyl)-2-(4-methoxyphenyl)-N,N-dimethylethanaminium chloride