Benzyl-ethyl-dimethyl-ammonium bromide.

The crystal structure of the title compound, C(11)H(18)N(+)·Br(-), has been determined as part of an ongoing study of the influence of the alkyl chain length on amphiphilic activity of quaternary ammonium salts. The title salt forms a three-dimensional network of ionic contacts through weak C-H⋯Br hydrogen bonds, with donor-acceptor distances in the range 3.757 (2)-3.959 (2) Å, in which methyl groups serve as donors.

Related literature

For related literature, see: Ogawa & Kuroda (1997 ▶); Hodorowicz et al. (2003 ▶, 2005 ▶); Kwolek et al. (2003 ▶); Allen et al. (1987 ▶).

Experimental

Crystal data

C11H18N+·Br−

M = 244.17

Orthorhombic,

a = 6.7765 (1) Å

b = 12.5827 (2) Å

c = 13.9433 (2) Å

V = 1188.90 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.42 mm−1

T = 293 (2) K

0.20 × 0.19 × 0.17 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO and SCALEPACK Otwinowski & Minor, 1997 ▶) T min = 0.548, T max = 0.594 (expected range = 0.516–0.559)

18366 measured reflections

3874 independent reflections

3483 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.065

S = 1.07

3874 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.49 e Å−3

Absolute structure: Flack (1983 ▶), with 1627 Friedel pairs

Flack parameter: 0.002 (9)

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002481/cf2179sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002481/cf2179Isup2.hkl

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

C11H18N+·Br–	F000 = 504
Mr = 244.17	Dx = 1.364 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2258 reflections
a = 6.7765 (1) Å	θ = 1.0–31.5º
b = 12.5827 (2) Å	µ = 3.42 mm−1
c = 13.9433 (2) Å	T = 293 (2) K
V = 1188.90 (3) Å3	Prism, colourless
Z = 4	0.20 × 0.19 × 0.17 mm

Nonius KappaCCD diffractometer	3874 independent reflections
Radiation source: fine-focus sealed tube	3483 reflections with I > 2σ(I)
Monochromator: horizontally mounted graphite crystal	Rint = 0.041
Detector resolution: 9 pixels mm-1	θmax = 31.5º
T = 293(2) K	θmin = 2.9º
φ and ω scans	h = 0→9
Absorption correction: multi-scan(DENZO and SCALEPACK Otwinowski & Minor, 1997)	k = 0→18
Tmin = 0.548, Tmax = 0.594	l = −20→20
18366 measured reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0247P)2 + 0.2756P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.027	(Δ/σ)max = 0.001
wR(F2) = 0.065	Δρmax = 0.26 e Å−3
S = 1.07	Δρmin = −0.49 e Å−3
3874 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
119 parameters	Extinction coefficient: 0.045 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1627 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.002 (9)
Hydrogen site location: inferred from neighbouring sites

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
Br1	0.29436 (3)	1.294368 (16)	0.812541 (14)	0.05290 (8)
N1	0.7787 (2)	1.06178 (12)	0.85616 (10)	0.0397 (3)
C1	0.8014 (4)	1.15508 (19)	0.92125 (17)	0.0613 (5)
H1A	0.7328	1.2150	0.8947	0.074*
H1B	0.9389	1.1720	0.9279	0.074*
H1C	0.7471	1.1383	0.9830	0.074*
C2	0.8857 (3)	0.9680 (2)	0.89734 (18)	0.0578 (5)
H2A	0.8706	0.9081	0.8554	0.069*
H2B	0.8317	0.9512	0.9591	0.069*
H2C	1.0232	0.9848	0.9039	0.069*
C31	0.7883 (5)	1.1763 (3)	0.70577 (19)	0.0808 (8)
H31A	0.8569	1.1845	0.6460	0.097*
H31B	0.8025	1.2399	0.7432	0.097*
H31C	0.6509	1.1635	0.6936	0.097*
C3	0.8734 (3)	1.08411 (19)	0.75980 (15)	0.0526 (5)
H3A	1.0130	1.0972	0.7698	0.063*
H3B	0.8617	1.0210	0.7203	0.063*
C4	0.5616 (2)	1.03466 (14)	0.84108 (12)	0.0373 (3)
H4A	0.4933	1.0982	0.8197	0.045*
H4B	0.5518	0.9824	0.7902	0.045*
C41	0.4578 (2)	0.99204 (13)	0.92838 (12)	0.0368 (3)
C42	0.3755 (3)	1.05941 (16)	0.99624 (14)	0.0483 (4)
H42	0.3879	1.1326	0.9892	0.058*
C43	0.2748 (4)	1.0181 (2)	1.07459 (15)	0.0617 (5)
H43	0.2222	1.0636	1.1205	0.074*
C44	0.2528 (3)	0.9094 (2)	1.08438 (16)	0.0645 (6)
H44	0.1860	0.8817	1.1370	0.077*
C45	0.3293 (4)	0.84284 (19)	1.01657 (18)	0.0619 (6)
H45	0.3126	0.7698	1.0229	0.074*
C46	0.4319 (3)	0.88285 (15)	0.93829 (16)	0.0477 (4)
H46	0.4832	0.8367	0.8925	0.057*

	U11	U22	U33	U12	U13	U23
Br1	0.06094 (12)	0.04546 (10)	0.05230 (11)	0.00357 (9)	0.00416 (9)	0.00747 (8)
N1	0.0369 (6)	0.0416 (7)	0.0405 (6)	−0.0039 (6)	−0.0001 (6)	−0.0024 (5)
C1	0.0611 (12)	0.0599 (12)	0.0629 (12)	−0.0199 (11)	0.0056 (12)	−0.0207 (10)
C2	0.0422 (9)	0.0646 (13)	0.0667 (13)	0.0038 (9)	−0.0115 (9)	0.0112 (10)
C31	0.0638 (13)	0.106 (2)	0.0727 (15)	0.0084 (16)	0.0168 (13)	0.0409 (14)
C3	0.0452 (9)	0.0642 (12)	0.0482 (10)	−0.0012 (9)	0.0100 (8)	0.0015 (9)
C4	0.0357 (7)	0.0384 (8)	0.0378 (7)	−0.0008 (6)	−0.0014 (6)	0.0000 (6)
C41	0.0356 (7)	0.0363 (8)	0.0386 (7)	−0.0027 (6)	−0.0026 (6)	0.0018 (6)
C42	0.0509 (9)	0.0470 (10)	0.0470 (9)	−0.0018 (8)	0.0061 (8)	−0.0034 (8)
C43	0.0592 (11)	0.0815 (15)	0.0444 (9)	−0.0056 (12)	0.0091 (10)	−0.0051 (10)
C44	0.0544 (13)	0.0901 (17)	0.0489 (10)	−0.0140 (11)	−0.0012 (8)	0.0251 (11)
C45	0.0603 (13)	0.0531 (11)	0.0722 (14)	−0.0119 (10)	−0.0057 (11)	0.0228 (10)
C46	0.0484 (9)	0.0363 (8)	0.0584 (10)	−0.0033 (7)	−0.0020 (9)	0.0034 (8)

Br1—N1	4.4393 (16)	C3—H3B	0.970
N1—C1	1.492 (2)	C4—C41	1.505 (2)
N1—C2	1.499 (3)	C4—H4A	0.970
N1—C3	1.515 (2)	C4—H4B	0.970
N1—C4	1.525 (2)	C41—C42	1.387 (3)
C1—H1A	0.960	C41—C46	1.392 (2)
C1—H1B	0.960	C42—C43	1.389 (3)
C1—H1C	0.960	C42—H42	0.930
C2—H2A	0.960	C43—C44	1.382 (4)
C2—H2B	0.960	C43—H43	0.930
C2—H2C	0.960	C44—C45	1.365 (4)
C31—C3	1.498 (3)	C44—H44	0.930
C31—H31A	0.960	C45—C46	1.388 (3)
C31—H31B	0.960	C45—H45	0.930
C31—H31C	0.960	C46—H46	0.930
C3—H3A	0.970
C1—N1—C2	109.66 (17)	C31—C3—H3A	108.5
C1—N1—C3	110.47 (16)	N1—C3—H3A	108.5
C2—N1—C3	106.30 (16)	C31—C3—H3B	108.5
C1—N1—C4	111.07 (16)	N1—C3—H3B	108.5
C2—N1—C4	110.08 (15)	H3A—C3—H3B	107.5
C3—N1—C4	109.15 (14)	C41—C4—N1	114.79 (13)
C1—N1—Br1	68.95 (13)	C41—C4—H4A	108.6
C2—N1—Br1	158.26 (12)	N1—C4—H4A	108.6
C3—N1—Br1	93.99 (11)	C41—C4—H4B	108.6
C4—N1—Br1	54.22 (8)	N1—C4—H4B	108.6
N1—C1—H1A	109.5	H4A—C4—H4B	107.5
N1—C1—H1B	109.5	C42—C41—C46	119.00 (18)
H1A—C1—H1B	109.5	C42—C41—C4	121.45 (15)
N1—C1—H1C	109.5	C46—C41—C4	119.40 (16)
H1A—C1—H1C	109.5	C41—C42—C43	120.3 (2)
H1B—C1—H1C	109.5	C41—C42—H42	119.8
N1—C2—H2A	109.5	C43—C42—H42	119.8
N1—C2—H2B	109.5	C44—C43—C42	120.1 (2)
H2A—C2—H2B	109.5	C44—C43—H43	120.0
N1—C2—H2C	109.5	C42—C43—H43	120.0
H2A—C2—H2C	109.5	C45—C44—C43	119.8 (2)
H2B—C2—H2C	109.5	C45—C44—H44	120.1
C3—C31—H31A	109.5	C43—C44—H44	120.1
C3—C31—H31B	109.5	C44—C45—C46	120.8 (2)
H31A—C31—H31B	109.5	C44—C45—H45	119.6
C3—C31—H31C	109.5	C46—C45—H45	119.6
H31A—C31—H31C	109.5	C45—C46—C41	119.9 (2)
H31B—C31—H31C	109.5	C45—C46—H46	120.0
C31—C3—N1	115.22 (18)	C41—C46—H46	120.0
C1—N1—C3—C31	−60.9 (3)	N1—C4—C41—C46	−98.94 (19)
C2—N1—C3—C31	−179.8 (2)	C46—C41—C42—C43	2.2 (3)
C4—N1—C3—C31	61.5 (2)	C4—C41—C42—C43	177.88 (19)
Br1—N1—C3—C31	8.1 (2)	C41—C42—C43—C44	−1.2 (3)
C1—N1—C4—C41	−68.2 (2)	C42—C43—C44—C45	−0.4 (4)
C2—N1—C4—C41	53.4 (2)	C43—C44—C45—C46	0.9 (4)
C3—N1—C4—C41	169.73 (15)	C44—C45—C46—C41	0.1 (3)
Br1—N1—C4—C41	−109.45 (15)	C42—C41—C46—C45	−1.6 (3)
N1—C4—C41—C42	85.4 (2)	C4—C41—C46—C45	−177.40 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Br1	0.96	3.34	4.144 (3)	143
C4—H4A···Br1	0.97	2.81	3.757 (2)	164
C42—H42···Br1	0.93	3.26	3.950 (2)	132
C31—H31C···Br1	0.96	3.36	3.953 (3)	122
C2—H2A···Br1i	0.96	2.96	3.850 (3)	154
C4—H4B···Br1i	0.97	2.96	3.832 (2)	151
C3—H3B···Br1i	0.97	3.08	3.950 (2)	151
C3—H3A···Br1ii	0.97	3.19	3.959 (2)	138
C1—H1C···Br1iii	0.96	2.99	3.766 (2)	139
C2—H2C···Cg1ii	0.96	2.69	3.526	145

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
C4—H4A⋯Br1	0.97	2.81	3.757 (2)	164
C2—H2A⋯Br1i	0.96	2.96	3.850 (3)	154
C4—H4B⋯Br1i	0.97	2.96	3.832 (2)	151
C3—H3B⋯Br1i	0.97	3.08	3.950 (2)	151
C3—H3A⋯Br1ii	0.97	3.19	3.959 (2)	138
C1—H1C⋯Br1iii	0.96	2.99	3.766 (2)	139
C2—H2C⋯Cg1ii	0.96	2.69	3.526	145

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