N-[2-(4-Bromo-benzo-yl)eth-yl]isopropyl-aminium chloride.

The crystal structure of the title compound, C(12)H(17)BrNO(+)·Cl(-), is stabilized by N-H⋯Cl and C-H⋯O hydrogen bonds, forming a three-dimensional network. The inter-actions framework is completed by C-H⋯π contacts between a methyl-ene group and the benzene ring of a symmetry-related mol-ecule.

Related literature

For details of the pharmacological effects of Mannich bases and for the synthesis, see: Dimmock & Kumar (1997 ▶); Gul, Gul, et al. (2005 ▶); Gul, Sahin et al. (2005 ▶); Gul et al. (2007 ▶); Mete et al. (2011 ▶); Kucukoglu et al. (2011 ▶); Canturk et al. (2008 ▶); Chen et al. (1991 ▶); Suleyman et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H17BrNO+·Cl−

M = 306.62

Tetragonal,

a = 19.7122 (4) Å

c = 7.1738 (2) Å

V = 2787.53 (11) Å3

Z = 8

Mo Kα radiation

μ = 3.12 mm−1

T = 294 K

0.15 × 0.13 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.632, T max = 0.709

50060 measured reflections

2836 independent reflections

1617 reflections with I > 2σ(I)

R int = 0.151

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.181

S = 1.07

2836 reflections

153 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.81 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); 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/S1600536811052640/bh2400sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052640/bh2400Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052640/bh2400Isup3.cml

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

C12H17BrNO+·Cl−	Dx = 1.461 Mg m−3
Mr = 306.62	Melting point: 447 K
Tetragonal, P42/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 4bc	Cell parameters from 3888 reflections
a = 19.7122 (4) Å	θ = 2.9–26.4°
c = 7.1738 (2) Å	µ = 3.12 mm−1
V = 2787.53 (11) Å3	T = 294 K
Z = 8	Block, white
F(000) = 1248	0.15 × 0.13 × 0.11 mm

Rigaku R-AXIS RAPID-S diffractometer	2836 independent reflections
Radiation source: Sealed Tube	1617 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.151
Detector resolution: 10.0000 pixels mm-1	θmax = 26.4°, θmin = 2.9°
dtprofit.ref scans	h = −24→24
Absorption correction: multi-scan (Blessing, 1995)	k = −24→24
Tmin = 0.632, Tmax = 0.709	l = −8→8
50060 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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0581P)2 + 4.3122P] where P = (Fo2 + 2Fc2)/3
2836 reflections	(Δ/σ)max < 0.001
153 parameters	Δρmax = 0.67 e Å−3
2 restraints	Δρmin = −0.81 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Br1	0.66757 (4)	0.19433 (5)	−0.04514 (15)	0.1156 (4)
O1	0.5235 (2)	0.0463 (2)	0.7192 (7)	0.0850 (17)
N1	0.6128 (2)	−0.1377 (2)	0.8767 (7)	0.0540 (17)
C1	0.6340 (3)	0.0359 (3)	0.3195 (9)	0.065 (2)
C2	0.6561 (3)	0.0740 (3)	0.1698 (10)	0.073 (3)
C3	0.6384 (3)	0.1411 (3)	0.1604 (10)	0.069 (2)
C4	0.5995 (3)	0.1707 (3)	0.2962 (10)	0.074 (3)
C5	0.5762 (3)	0.1323 (3)	0.4438 (9)	0.067 (2)
C6	0.5940 (3)	0.0644 (3)	0.4585 (8)	0.057 (2)
C7	0.5686 (3)	0.0245 (3)	0.6205 (9)	0.061 (2)
C8	0.5994 (3)	−0.0435 (3)	0.6592 (8)	0.063 (2)
C9	0.5742 (3)	−0.0744 (3)	0.8392 (9)	0.061 (2)
C10	0.5984 (3)	−0.1725 (3)	1.0610 (8)	0.0583 (19)
C11	0.6462 (3)	−0.2324 (3)	1.0768 (9)	0.070 (2)
C12	0.5251 (3)	−0.1928 (3)	1.0763 (8)	0.069 (2)
Cl1	0.75617 (8)	−0.07602 (8)	0.9322 (2)	0.0682 (6)
H1	0.64610	−0.00960	0.32750	0.0780*
HN1	0.604 (4)	−0.168 (3)	0.794 (9)	0.1390*
HN2	0.6548 (13)	−0.126 (4)	0.877 (12)	0.1390*
H2	0.68250	0.05440	0.07690	0.0870*
H4	0.58890	0.21660	0.28900	0.0890*
H5	0.54840	0.15200	0.53360	0.0800*
H8A	0.64830	−0.03880	0.66520	0.0760*
H8B	0.58880	−0.07390	0.55690	0.0760*
H9A	0.58050	−0.04270	0.94100	0.0730*
H9B	0.52610	−0.08460	0.82920	0.0730*
H10	0.60870	−0.14060	1.16200	0.0700*
H11A	0.63550	−0.26500	0.98190	0.1050*
H11B	0.64120	−0.25290	1.19730	0.1050*
H11C	0.69210	−0.21710	1.06120	0.1050*
H12A	0.51320	−0.22120	0.97260	0.1030*
H12B	0.49710	−0.15300	1.07580	0.1030*
H12C	0.51820	−0.21730	1.19040	0.1030*

	U11	U22	U33	U12	U13	U23
Br1	0.0916 (6)	0.1139 (7)	0.1414 (9)	0.0018 (4)	0.0247 (5)	0.0597 (6)
O1	0.091 (3)	0.074 (3)	0.090 (3)	0.020 (2)	0.021 (3)	0.008 (3)
N1	0.055 (3)	0.049 (3)	0.058 (3)	0.002 (2)	−0.001 (2)	0.007 (2)
C1	0.061 (4)	0.055 (4)	0.080 (4)	0.009 (3)	−0.003 (3)	0.007 (3)
C2	0.067 (4)	0.067 (4)	0.084 (5)	0.003 (3)	0.006 (3)	0.011 (4)
C3	0.049 (3)	0.070 (4)	0.087 (5)	−0.006 (3)	−0.004 (3)	0.023 (4)
C4	0.075 (4)	0.056 (4)	0.090 (5)	0.002 (3)	−0.008 (4)	0.013 (4)
C5	0.072 (4)	0.051 (3)	0.077 (4)	0.005 (3)	−0.003 (3)	0.000 (3)
C6	0.062 (4)	0.050 (3)	0.060 (4)	−0.002 (3)	−0.010 (3)	0.004 (3)
C7	0.056 (4)	0.060 (4)	0.068 (4)	0.000 (3)	−0.004 (3)	−0.001 (3)
C8	0.064 (4)	0.061 (4)	0.065 (4)	0.006 (3)	0.001 (3)	0.009 (3)
C9	0.060 (4)	0.053 (3)	0.070 (4)	0.003 (3)	−0.003 (3)	0.005 (3)
C10	0.068 (4)	0.056 (3)	0.051 (3)	−0.003 (3)	−0.004 (3)	0.005 (3)
C11	0.070 (4)	0.072 (4)	0.067 (4)	0.009 (3)	−0.008 (3)	0.013 (3)
C12	0.067 (4)	0.075 (4)	0.064 (4)	−0.004 (3)	0.008 (3)	0.006 (3)
Cl1	0.0608 (9)	0.0857 (11)	0.0580 (9)	−0.0135 (7)	0.0045 (7)	−0.0045 (8)

Br1—C3	1.899 (7)	C10—C11	1.515 (8)
O1—C7	1.215 (7)	C1—H1	0.9300
N1—C9	1.486 (7)	C2—H2	0.9300
N1—C10	1.516 (8)	C4—H4	0.9300
N1—HN2	0.86 (4)	C5—H5	0.9300
N1—HN1	0.86 (6)	C8—H8A	0.9700
C1—C2	1.381 (9)	C8—H8B	0.9700
C1—C6	1.390 (9)	C9—H9A	0.9700
C2—C3	1.370 (8)	C9—H9B	0.9700
C3—C4	1.370 (9)	C10—H10	0.9800
C4—C5	1.380 (9)	C11—H11A	0.9600
C5—C6	1.388 (8)	C11—H11B	0.9600
C6—C7	1.490 (9)	C11—H11C	0.9600
C7—C8	1.498 (8)	C12—H12A	0.9600
C8—C9	1.512 (9)	C12—H12B	0.9600
C10—C12	1.503 (8)	C12—H12C	0.9600
C9—N1—C10	116.2 (4)	C5—C4—H4	120.00
HN2—N1—HN1	113 (8)	C4—C5—H5	120.00
C9—N1—HN1	111 (5)	C6—C5—H5	120.00
C10—N1—HN2	107 (6)	C7—C8—H8A	109.00
C9—N1—HN2	106 (5)	C7—C8—H8B	109.00
C10—N1—HN1	105 (4)	C9—C8—H8A	109.00
C2—C1—C6	121.1 (6)	C9—C8—H8B	109.00
C1—C2—C3	118.9 (6)	H8A—C8—H8B	108.00
Br1—C3—C2	119.7 (5)	N1—C9—H9A	110.00
Br1—C3—C4	119.1 (5)	N1—C9—H9B	110.00
C2—C3—C4	121.3 (6)	C8—C9—H9A	110.00
C3—C4—C5	119.9 (6)	C8—C9—H9B	110.00
C4—C5—C6	120.2 (6)	H9A—C9—H9B	108.00
C5—C6—C7	118.9 (5)	N1—C10—H10	108.00
C1—C6—C7	122.5 (5)	C11—C10—H10	108.00
C1—C6—C5	118.6 (5)	C12—C10—H10	108.00
O1—C7—C6	120.9 (5)	C10—C11—H11A	109.00
C6—C7—C8	118.7 (5)	C10—C11—H11B	109.00
O1—C7—C8	120.3 (6)	C10—C11—H11C	109.00
C7—C8—C9	112.7 (5)	H11A—C11—H11B	110.00
N1—C9—C8	109.0 (5)	H11A—C11—H11C	110.00
N1—C10—C12	111.4 (5)	H11B—C11—H11C	110.00
C11—C10—C12	112.6 (5)	C10—C12—H12A	109.00
N1—C10—C11	107.5 (5)	C10—C12—H12B	110.00
C2—C1—H1	119.00	C10—C12—H12C	109.00
C6—C1—H1	119.00	H12A—C12—H12B	109.00
C1—C2—H2	121.00	H12A—C12—H12C	109.00
C3—C2—H2	121.00	H12B—C12—H12C	109.00
C3—C4—H4	120.00
C9—N1—C10—C11	−176.0 (5)	C3—C4—C5—C6	2.3 (9)
C9—N1—C10—C12	60.1 (6)	C4—C5—C6—C1	−1.7 (9)
C10—N1—C9—C8	174.9 (4)	C4—C5—C6—C7	179.4 (6)
C6—C1—C2—C3	0.5 (9)	C5—C6—C7—C8	−166.9 (5)
C2—C1—C6—C5	0.3 (9)	C1—C6—C7—O1	−165.4 (6)
C2—C1—C6—C7	179.2 (6)	C1—C6—C7—C8	14.2 (9)
C1—C2—C3—C4	0.1 (10)	C5—C6—C7—O1	13.5 (9)
C1—C2—C3—Br1	−179.5 (5)	O1—C7—C8—C9	−6.8 (8)
C2—C3—C4—C5	−1.4 (10)	C6—C7—C8—C9	173.6 (5)
Br1—C3—C4—C5	178.1 (5)	C7—C8—C9—N1	−173.8 (5)

Cg1 is the centroid of the benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN2···Cl1	0.86 (4)	2.26 (4)	3.102 (4)	166 (5)
N1—HN1···Cl1i	0.86 (6)	2.27 (6)	3.133 (5)	177 (9)
C12—H12B···O1ii	0.96	2.60	3.378 (7)	139
C9—H9B···Cg1iii	0.97	3.00	3.943 (6)	164

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN2⋯Cl1	0.86 (4)	2.26 (4)	3.102 (4)	166 (5)
N1—HN1⋯Cl1i	0.86 (6)	2.27 (6)	3.133 (5)	177 (9)
C12—H12B⋯O1ii	0.96	2.60	3.378 (7)	139
C9—H9B⋯Cg1iii	0.97	3.00	3.943 (6)	164

Symmetry codes: (i) ; (ii) ; (iii) .