N-(2-Benzoyl-eth-yl)propan-2-aminium chloride.

In the title salt, C(12)H(18)NO(+)·Cl(-), N-H⋯Cl inter-actions between the free chloride anions and the organic cations connect the mol-ecules into hydrogen-bond dimers, forming a R(2) (2)(8) motif. The dimers are linked by C-H⋯O hydrogen bonds into chains extending along [301]. The carbonyl group is co-planar with the phenyl ring [C-C-C=O torsion angle = -3.3 (7)°]. The side chain has an E conformation.

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 ▶); Mete et al. (2011a ▶,b ▶); Kucuk­oglu et al. (2011 ▶); Canturk et al. (2008 ▶); Chen et al. (1991 ▶); Gul (2005 ▶); Suleyman et al. (2007 ▶); Plati et al. (1949 ▶). For bond-length data, see: Allen et al. (1987 ▶). For n class="Chemical">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

C12H18NO+·Cl−

M = 227.72

Monoclinic,

a = 8.036 (5) Å

b = 8.656 (5) Å

c = 18.403 (5) Å

β = 97.174 (5)°

V = 1270.1 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 294 K

0.16 × 0.13 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.958, T max = 0.967

15799 measured reflections

2334 independent reflections

1204 reflections with I > 2σ(I)

R int = 0.116

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.224

S = 1.05

2334 reflections

145 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536812035106/qm2079sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035106/qm2079Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035106/qm2079Isup3.cml

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

C12H18NO+·Cl−	F(000) = 488
Mr = 227.72	Dx = 1.191 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3090 reflections
a = 8.036 (5) Å	θ = 2.2–26.4°
b = 8.656 (5) Å	µ = 0.28 mm−1
c = 18.403 (5) Å	T = 294 K
β = 97.174 (5)°	Block, white
V = 1270.1 (11) Å3	0.16 × 0.13 × 0.12 mm
Z = 4

Rigaku R-AXIS RAPID-S diffractometer	2334 independent reflections
Radiation source: Sealed Tube	1204 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.116
Detector resolution: 10.0000 pixels mm-1	θmax = 25.5°, θmin = 2.2°
dtprofit.ref scans	h = −9→9
Absorption correction: multi-scan (Blessing, 1995)	k = −9→10
Tmin = 0.958, Tmax = 0.967	l = −22→22
15799 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.224	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0971P)2 + 0.2008P] where P = (Fo2 + 2Fc2)/3
2334 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.49 e Å−3
2 restraints	Δρmin = −0.19 e Å−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	0.2324 (5)	0.4012 (5)	1.02649 (18)	0.1262 (18)
N1	0.3982 (4)	0.4236 (4)	0.8222 (2)	0.0689 (14)
C1	−0.1184 (6)	0.1831 (6)	0.9398 (3)	0.090 (2)
C2	−0.2586 (7)	0.1067 (7)	0.9575 (4)	0.114 (3)
C3	−0.2887 (7)	0.0999 (7)	1.0303 (4)	0.110 (3)
C4	−0.1824 (7)	0.1686 (8)	1.0833 (3)	0.103 (3)
C5	−0.0433 (7)	0.2458 (6)	1.0658 (3)	0.088 (2)
C6	−0.0099 (6)	0.2528 (5)	0.9940 (2)	0.0722 (17)
C7	0.1440 (6)	0.3359 (6)	0.9778 (3)	0.0828 (19)
C8	0.1897 (5)	0.3369 (5)	0.9007 (2)	0.0749 (17)
C9	0.3548 (5)	0.4217 (5)	0.8982 (2)	0.0772 (17)
C10	0.5624 (6)	0.5009 (5)	0.8146 (3)	0.0850 (19)
C11	0.6181 (8)	0.4545 (7)	0.7460 (4)	0.133 (3)
C12	0.5461 (6)	0.6727 (6)	0.8219 (3)	0.109 (3)
Cl1	0.40593 (14)	0.07597 (13)	0.77578 (6)	0.0828 (5)
H1	−0.09700	0.18770	0.89130	0.1080*
H1N	0.321 (5)	0.453 (5)	0.788 (2)	0.0990*
H2	−0.33240	0.06020	0.92100	0.1370*
H2N	0.402 (6)	0.332 (3)	0.803 (2)	0.0990*
H3	−0.38260	0.04780	1.04250	0.1320*
H4	−0.20350	0.16370	1.13180	0.1240*
H5	0.02880	0.29350	1.10240	0.1060*
H8A	0.10170	0.38750	0.86830	0.0900*
H8B	0.19980	0.23160	0.88380	0.0900*
H9A	0.34510	0.52680	0.91550	0.0930*
H9B	0.44310	0.37050	0.93010	0.0930*
H10	0.64530	0.46460	0.85460	0.1020*
H11A	0.53580	0.48440	0.70610	0.1990*
H11B	0.63260	0.34440	0.74560	0.1990*
H11C	0.72290	0.50400	0.74080	0.1990*
H12A	0.65050	0.72110	0.81500	0.1630*
H12B	0.51800	0.69720	0.86970	0.1630*
H12C	0.45930	0.70980	0.78540	0.1630*

	U11	U22	U33	U12	U13	U23
O1	0.151 (3)	0.161 (4)	0.065 (2)	−0.063 (3)	0.007 (2)	−0.016 (2)
N1	0.065 (2)	0.066 (2)	0.076 (3)	−0.0063 (19)	0.0105 (16)	0.0006 (18)
C1	0.093 (4)	0.099 (4)	0.083 (3)	−0.006 (3)	0.027 (3)	−0.010 (3)
C2	0.082 (4)	0.143 (6)	0.119 (5)	−0.017 (3)	0.022 (3)	−0.019 (4)
C3	0.087 (4)	0.138 (5)	0.113 (5)	0.003 (3)	0.039 (4)	0.015 (4)
C4	0.091 (4)	0.136 (5)	0.086 (4)	0.025 (4)	0.028 (3)	0.020 (3)
C5	0.094 (4)	0.102 (4)	0.069 (3)	0.013 (3)	0.012 (3)	0.003 (3)
C6	0.078 (3)	0.072 (3)	0.068 (3)	0.009 (2)	0.015 (2)	−0.002 (2)
C7	0.097 (4)	0.086 (3)	0.065 (3)	0.002 (3)	0.009 (2)	−0.003 (2)
C8	0.084 (3)	0.075 (3)	0.067 (3)	−0.007 (2)	0.015 (2)	−0.001 (2)
C9	0.081 (3)	0.078 (3)	0.072 (3)	−0.004 (2)	0.007 (2)	0.002 (2)
C10	0.069 (3)	0.069 (3)	0.118 (4)	−0.005 (2)	0.016 (3)	0.003 (3)
C11	0.127 (5)	0.131 (5)	0.151 (6)	−0.037 (4)	0.061 (4)	−0.027 (4)
C12	0.090 (4)	0.069 (3)	0.168 (6)	−0.015 (3)	0.021 (3)	0.002 (3)
Cl1	0.0792 (8)	0.0703 (8)	0.0974 (9)	0.0004 (6)	0.0050 (6)	−0.0080 (6)

O1—C7	1.212 (6)	C1—H1	0.9300
N1—C9	1.483 (5)	C2—H2	0.9300
N1—C10	1.502 (6)	C3—H3	0.9300
N1—H1N	0.87 (4)	C4—H4	0.9300
N1—H2N	0.87 (3)	C5—H5	0.9300
C1—C2	1.380 (8)	C8—H8A	0.9700
C1—C6	1.379 (7)	C8—H8B	0.9700
C2—C3	1.392 (10)	C9—H9A	0.9700
C3—C4	1.352 (9)	C9—H9B	0.9700
C4—C5	1.375 (8)	C10—H10	0.9800
C5—C6	1.382 (7)	C11—H11A	0.9600
C6—C7	1.493 (7)	C11—H11B	0.9600
C7—C8	1.509 (7)	C11—H11C	0.9600
C8—C9	1.522 (6)	C12—H12A	0.9600
C10—C12	1.500 (7)	C12—H12B	0.9600
C10—C11	1.448 (9)	C12—H12C	0.9600
C9—N1—C10	113.9 (3)	C5—C4—H4	120.00
C10—N1—H1N	111 (3)	C4—C5—H5	120.00
C9—N1—H1N	117 (3)	C6—C5—H5	120.00
C9—N1—H2N	113 (2)	C7—C8—H8A	110.00
C10—N1—H2N	107 (3)	C7—C8—H8B	110.00
H1N—N1—H2N	92 (4)	C9—C8—H8A	110.00
C2—C1—C6	120.0 (5)	C9—C8—H8B	110.00
C1—C2—C3	119.5 (6)	H8A—C8—H8B	108.00
C2—C3—C4	120.4 (5)	N1—C9—H9A	110.00
C3—C4—C5	120.3 (5)	N1—C9—H9B	110.00
C4—C5—C6	120.4 (5)	C8—C9—H9A	110.00
C5—C6—C7	118.5 (4)	C8—C9—H9B	110.00
C1—C6—C7	122.1 (4)	H9A—C9—H9B	108.00
C1—C6—C5	119.4 (5)	N1—C10—H10	108.00
O1—C7—C6	120.1 (5)	C11—C10—H10	108.00
C6—C7—C8	119.7 (4)	C12—C10—H10	108.00
O1—C7—C8	120.2 (4)	C10—C11—H11A	109.00
C7—C8—C9	110.3 (3)	C10—C11—H11B	109.00
N1—C9—C8	110.0 (3)	C10—C11—H11C	109.00
N1—C10—C12	110.2 (4)	H11A—C11—H11B	110.00
C11—C10—C12	113.1 (5)	H11A—C11—H11C	109.00
N1—C10—C11	109.2 (4)	H11B—C11—H11C	109.00
C2—C1—H1	120.00	C10—C12—H12A	109.00
C6—C1—H1	120.00	C10—C12—H12B	110.00
C1—C2—H2	120.00	C10—C12—H12C	109.00
C3—C2—H2	120.00	H12A—C12—H12B	110.00
C2—C3—H3	120.00	H12A—C12—H12C	109.00
C4—C3—H3	120.00	H12B—C12—H12C	109.00
C3—C4—H4	120.00
C10—N1—C9—C8	−178.2 (3)	C4—C5—C6—C1	0.7 (8)
C9—N1—C10—C11	161.9 (4)	C4—C5—C6—C7	−179.1 (5)
C9—N1—C10—C12	−73.3 (5)	C5—C6—C7—C8	176.1 (4)
C2—C1—C6—C7	179.6 (5)	C1—C6—C7—O1	176.9 (5)
C6—C1—C2—C3	−0.4 (8)	C1—C6—C7—C8	−3.7 (7)
C2—C1—C6—C5	−0.2 (8)	C5—C6—C7—O1	−3.3 (7)
C1—C2—C3—C4	0.6 (9)	O1—C7—C8—C9	2.1 (6)
C2—C3—C4—C5	−0.1 (10)	C6—C7—C8—C9	−177.3 (4)
C3—C4—C5—C6	−0.6 (9)	C7—C8—C9—N1	−179.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1i	0.87 (4)	2.30 (4)	3.141 (4)	163 (4)
N1—H2N···Cl1	0.87 (3)	2.27 (3)	3.131 (4)	169 (4)
C10—H10···O1ii	0.98	2.56	3.284 (7)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl1i	0.87 (4)	2.30 (4)	3.141 (4)	163 (4)
N1—H2N⋯Cl1	0.87 (3)	2.27 (3)	3.131 (4)	169 (4)
C10—H10⋯O1ii	0.98	2.56	3.284 (7)	130

Symmetry codes: (i) ; (ii) .