N-[2-(4-Methyl-benzo-yl)eth-yl]propan-2-aminium chloride.

In the title compound, C(13)H(20)NO(+)·Cl(-), the protonated amino N atom is hydrogen bonded to the chloride anion. N-H⋯Cl hydrogen bonds link the anions and cations into dimers, which are connected by C-H⋯O hydrogen bonds, forming supra-molecular chains extending along [100].

Related literature

For the details of the pharmacological effects of Mannich bases and for their synthesis, see: Dimmock & Kumar (1997 ▶); Gul et al. (2004 ▶; 2005a ▶,b ▶; 2009 ▶); Gul (2005 ▶); Mete et al. (2011a ▶,b ▶); Kucukoglu et al. (2011 ▶); Canturk et al. (2008 ▶); Chen et al. (1991 ▶); Suleyman et al. (2007 ▶); Plastino et al. (1962 ▶, 1964 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter (1990 ▶). For some related structures, see: Abonia et al. (2011 ▶); Tuzina et al. (2006 ▶).

Experimental

Crystal data

C13H20NO+·Cl−

M = 241.75

Monoclinic,

a = 7.786 (5) Å

b = 7.511 (5) Å

c = 23.365 (5) Å

β = 95.362 (5)°

V = 1360.4 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 294 K

0.17 × 0.11 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.966, T max = 0.974

26900 measured reflections

2800 independent reflections

2007 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.151

S = 1.06

2800 reflections

149 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear (Rigaku/MSC, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035271/qm2078sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035271/qm2078Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035271/qm2078Isup3.cml

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

C13H20NO+·Cl−	F(000) = 520
Mr = 241.75	Dx = 1.180 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4594 reflections
a = 7.786 (5) Å	θ = 2.6–26.5°
b = 7.511 (5) Å	µ = 0.26 mm−1
c = 23.365 (5) Å	T = 294 K
β = 95.362 (5)°	Block, white
V = 1360.4 (13) Å3	0.17 × 0.11 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID-S diffractometer	2800 independent reflections
Radiation source: Sealed Tube	2007 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.066
Detector resolution: 10.0000 pixels mm-1	θmax = 26.4°, θmin = 2.6°
dtprofit.ref scans	h = −9→9
Absorption correction: multi-scan (Blessing, 1995)	k = −8→9
Tmin = 0.966, Tmax = 0.974	l = −29→29
26900 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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.151	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.2172P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2800 reflections	Δρmax = 0.21 e Å−3
149 parameters	Δρmin = −0.18 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: 0.010 (3)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1	0.7123 (2)	0.2422 (3)	0.57107 (8)	0.0903 (8)
N1	0.7916 (2)	0.0622 (2)	0.74056 (7)	0.0555 (6)
C1	1.2949 (3)	0.1740 (3)	0.53020 (10)	0.0722 (9)
C2	1.2627 (3)	0.2488 (3)	0.47633 (10)	0.0653 (8)
C3	1.0947 (3)	0.2961 (3)	0.45820 (9)	0.0680 (9)
C4	0.9644 (3)	0.2737 (3)	0.49337 (9)	0.0659 (8)
C5	0.9974 (3)	0.2024 (3)	0.54815 (9)	0.0563 (7)
C6	1.1652 (3)	0.1501 (3)	0.56544 (10)	0.0658 (8)
C7	0.8564 (3)	0.1895 (3)	0.58624 (9)	0.0616 (8)
C8	0.8956 (3)	0.1133 (3)	0.64590 (9)	0.0623 (8)
C9	0.7524 (3)	0.1489 (3)	0.68361 (9)	0.0606 (8)
C10	0.6625 (3)	0.0981 (3)	0.78362 (9)	0.0611 (8)
C11	0.6888 (4)	0.2830 (4)	0.80850 (12)	0.0807 (10)
C12	0.6811 (4)	−0.0436 (4)	0.82927 (12)	0.0864 (10)
C13	1.4074 (4)	0.2830 (5)	0.43891 (12)	0.0913 (11)
Cl1	1.17234 (7)	0.15576 (7)	0.78840 (2)	0.0665 (2)
H1	1.40660	0.13910	0.54290	0.0870*
H3	1.06950	0.34370	0.42160	0.0820*
H4	0.85250	0.30690	0.48030	0.0790*
H6	1.19010	0.09810	0.60140	0.0790*
H8A	0.91290	−0.01420	0.64310	0.0750*
H8B	1.00180	0.16520	0.66350	0.0750*
H9A	0.73980	0.27620	0.68870	0.0730*
H9B	0.64450	0.10290	0.66530	0.0730*
H10	0.54610	0.09070	0.76380	0.0730*
H11A	0.59650	0.31080	0.83150	0.1210*
H11B	0.68980	0.36790	0.77780	0.1210*
H11C	0.79670	0.28780	0.83190	0.1210*
H12A	0.66880	−0.15880	0.81160	0.1290*
H12B	0.59360	−0.02790	0.85520	0.1290*
H12C	0.79290	−0.03440	0.85020	0.1290*
H13A	1.43820	0.40670	0.44090	0.1370*
H13B	1.37010	0.25180	0.39990	0.1370*
H13C	1.50570	0.21210	0.45220	0.1370*
H14A	0.89610	0.09920	0.75560	0.0670*
H14B	0.79790	−0.05620	0.73520	0.0670*

	U11	U22	U33	U12	U13	U23
O1	0.0562 (10)	0.1386 (17)	0.0763 (11)	0.0110 (11)	0.0077 (8)	0.0214 (11)
N1	0.0530 (10)	0.0541 (10)	0.0609 (10)	−0.0019 (8)	0.0135 (8)	0.0028 (8)
C1	0.0545 (13)	0.0940 (19)	0.0683 (15)	0.0016 (12)	0.0076 (11)	0.0037 (13)
C2	0.0651 (14)	0.0730 (15)	0.0596 (13)	−0.0076 (12)	0.0152 (10)	−0.0054 (11)
C3	0.0723 (16)	0.0783 (16)	0.0541 (13)	−0.0016 (12)	0.0094 (10)	0.0048 (11)
C4	0.0618 (14)	0.0764 (15)	0.0596 (13)	−0.0001 (12)	0.0057 (10)	0.0003 (11)
C5	0.0553 (12)	0.0579 (12)	0.0555 (12)	−0.0054 (10)	0.0048 (9)	−0.0023 (9)
C6	0.0625 (14)	0.0774 (16)	0.0577 (12)	0.0004 (11)	0.0066 (10)	0.0071 (11)
C7	0.0557 (13)	0.0684 (14)	0.0609 (13)	−0.0038 (11)	0.0059 (10)	−0.0008 (10)
C8	0.0574 (13)	0.0718 (14)	0.0588 (13)	−0.0014 (11)	0.0111 (10)	0.0039 (11)
C9	0.0584 (13)	0.0630 (14)	0.0614 (13)	0.0002 (10)	0.0103 (10)	0.0041 (10)
C10	0.0535 (12)	0.0672 (14)	0.0653 (13)	0.0004 (10)	0.0195 (10)	0.0012 (10)
C11	0.0901 (19)	0.0698 (16)	0.0871 (18)	0.0072 (13)	0.0350 (14)	−0.0041 (13)
C12	0.108 (2)	0.0767 (17)	0.0808 (17)	0.0039 (15)	0.0418 (15)	0.0138 (13)
C13	0.0797 (18)	0.120 (2)	0.0775 (18)	−0.0034 (17)	0.0253 (14)	0.0074 (16)
Cl1	0.0631 (4)	0.0604 (4)	0.0756 (4)	0.0010 (3)	0.0046 (3)	−0.0014 (3)

O1—C7	1.211 (3)	C3—H3	0.9300
N1—C9	1.487 (3)	C4—H4	0.9300
N1—C10	1.511 (3)	C6—H6	0.9300
N1—H14B	0.9000	C8—H8A	0.9700
N1—H14A	0.9000	C8—H8B	0.9700
C1—C6	1.373 (3)	C9—H9A	0.9700
C1—C2	1.380 (3)	C9—H9B	0.9700
C2—C3	1.383 (3)	C10—H10	0.9800
C2—C13	1.511 (4)	C11—H11A	0.9600
C3—C4	1.374 (3)	C11—H11B	0.9600
C4—C5	1.389 (3)	C11—H11C	0.9600
C5—C7	1.480 (3)	C12—H12A	0.9600
C5—C6	1.388 (3)	C12—H12B	0.9600
C7—C8	1.511 (3)	C12—H12C	0.9600
C8—C9	1.508 (3)	C13—H13A	0.9600
C10—C12	1.504 (4)	C13—H13B	0.9600
C10—C11	1.512 (4)	C13—H13C	0.9600
C1—H1	0.9300
C9—N1—C10	115.08 (16)	C7—C8—H8A	109.00
H14A—N1—H14B	107.00	C7—C8—H8B	109.00
C9—N1—H14B	109.00	C9—C8—H8A	109.00
C10—N1—H14A	109.00	C9—C8—H8B	109.00
C9—N1—H14A	108.00	H8A—C8—H8B	108.00
C10—N1—H14B	108.00	N1—C9—H9A	110.00
C2—C1—C6	121.3 (2)	N1—C9—H9B	110.00
C1—C2—C13	121.0 (2)	C8—C9—H9A	110.00
C1—C2—C3	118.0 (2)	C8—C9—H9B	110.00
C3—C2—C13	120.9 (2)	H9A—C9—H9B	108.00
C2—C3—C4	121.0 (2)	N1—C10—H10	109.00
C3—C4—C5	121.0 (2)	C11—C10—H10	109.00
C6—C5—C7	122.5 (2)	C12—C10—H10	109.00
C4—C5—C7	119.7 (2)	C10—C11—H11A	109.00
C4—C5—C6	117.7 (2)	C10—C11—H11B	109.00
C1—C6—C5	120.9 (2)	C10—C11—H11C	109.00
O1—C7—C5	121.5 (2)	H11A—C11—H11B	109.00
C5—C7—C8	118.8 (2)	H11A—C11—H11C	110.00
O1—C7—C8	119.7 (2)	H11B—C11—H11C	109.00
C7—C8—C9	112.03 (19)	C10—C12—H12A	109.00
N1—C9—C8	110.12 (18)	C10—C12—H12B	109.00
N1—C10—C12	108.65 (19)	C10—C12—H12C	109.00
C11—C10—C12	112.1 (2)	H12A—C12—H12B	110.00
N1—C10—C11	110.19 (19)	H12A—C12—H12C	109.00
C2—C1—H1	119.00	H12B—C12—H12C	109.00
C6—C1—H1	119.00	C2—C13—H13A	109.00
C2—C3—H3	119.00	C2—C13—H13B	109.00
C4—C3—H3	119.00	C2—C13—H13C	109.00
C3—C4—H4	119.00	H13A—C13—H13B	110.00
C5—C4—H4	120.00	H13A—C13—H13C	109.00
C1—C6—H6	120.00	H13B—C13—H13C	109.00
C5—C6—H6	120.00
C9—N1—C10—C11	−76.7 (2)	C3—C4—C5—C7	176.5 (2)
C9—N1—C10—C12	160.08 (19)	C4—C5—C6—C1	2.2 (3)
C10—N1—C9—C8	176.31 (17)	C7—C5—C6—C1	−176.0 (2)
C6—C1—C2—C3	−1.3 (3)	C6—C5—C7—C8	−1.2 (3)
C6—C1—C2—C13	177.0 (2)	C4—C5—C7—O1	−1.1 (3)
C2—C1—C6—C5	−0.7 (4)	C4—C5—C7—C8	−179.4 (2)
C13—C2—C3—C4	−176.6 (2)	C6—C5—C7—O1	177.1 (2)
C1—C2—C3—C4	1.7 (3)	O1—C7—C8—C9	−11.9 (3)
C2—C3—C4—C5	−0.2 (3)	C5—C7—C8—C9	166.46 (19)
C3—C4—C5—C6	−1.8 (3)	C7—C8—C9—N1	176.54 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H14A···Cl1	0.90	2.26	3.148 (3)	172
N1—H14B···Cl1i	0.90	2.25	3.145 (3)	173
C1—H1···O1ii	0.93	2.53	3.340 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H14A⋯Cl1	0.90	2.26	3.148 (3)	172
N1—H14B⋯Cl1i	0.90	2.25	3.145 (3)	173
C1—H1⋯O1ii	0.93	2.53	3.340 (4)	146

Symmetry codes: (i) ; (ii) .