2-(Cyclo-hexa-1,4-dien-yl)-2-(4-methoxy-phen-yl)-N,N-dimethyl-ethanaminium chloride.

In the title compound, C(17)H(24)NO(+)·Cl(-), the cyclo-hexa-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, inter-molecular N-H⋯Cl and C-H⋯Cl hydrogen bonds link the mol-ecules 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 = 293.84

Orthorhombic,

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 (; Higashi, 1995 ▶) T min = 0.927, T max = 0.979

32170 measured reflections

4010 independent reflections

2102 reflections with F 2 > 2σ(F 2)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.140

S = 1.00

4010 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.46 e Å−3

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.

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

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

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

C17H24NO+·Cl−	F(000) = 1264.00
Mr = 293.84	Dx = 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

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

Refinement on F2	w = 1/[0.0003Fo2 + 1.2σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.060	(Δ/σ)max < 0.001
wR(F2) = 0.140	Δρmax = 0.61 e Å−3
S = 1.00	Δρmin = −0.46 e Å−3
4010 reflections	Extinction correction: Larson (1970)
182 parameters	Extinction coefficient: 41 (8)
H-atom parameters constrained

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).

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .