Literature DB >> 21582850

Bis(2-chloro-benz-yl)dimethyl-ammonium bromide.

Tariq Mahmud, Javed Iqbal, Mark R J Elsegood, Vickie McKee.   

Abstract

In the title compound, C(16)H(18)Cl(2)N(+)·Br(-), the dihedral angle between the aromatic ring planes is 57.73 (5)°. In the absence of any strong hydrogen bonds, the structure results from a large number of competing weaker inter-actions including Cl⋯Cl [3.4610 (5) Å] and C-H⋯Cl contacts and both (aryl) C-H⋯Br and N(+)-Csp(3)-H⋯Br(-) cation-anion inter-actions.

Entities:  

Year:  2009        PMID： 21582850      PMCID： PMC2969506          DOI： 10.1107/S160053680902159X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

Routes to quaternary ammonium compounds include the action of hexa­decyl halide on heterocycles such as pyridine (Shelton & Mariemont, 1942 ▶); the action of 1-haloalkanes and allied compounds on the higher alkyl esters of p-dimethyl­amino benzoic acid (Piggot & Woolvin, 1940 ▶); reaction of a terminal ep­oxy group with tertiary amine followed by the addition of an acid (Horst & Manfred, 1983 ▶); reaction of a tertiary amine, an alkyl­ating agent and an ep­oxy compound (Gary & Owen, 1991 ▶); reaction of an alkyl halide with pyridine or imidazole at 393 to 623 K (Kimihiko et al., 2002 ▶); and reaction of tertiary amines, methanol and a cyclic ester (Walker, 2004 ▶). Quaternary ammonium compounds are utilized in many industrial processes, across a wide range of processes from sanitisers in detergent (Peng et al., 2002 ▶) to phase transfer catalysis (Stark et al., 2004 ▶)). For Cl⋯Cl and C—H⋯Cl contacts, see: (López-Duplá, et al. 2003 ▶); (Desiraju & Steiner, 1999 ▶).

Experimental

Crystal data

C16H18Cl2N+·Br− M = 375.12 Monoclinic, a = 11.9427 (5) Å b = 8.9771 (4) Å c = 15.0759 (6) Å β = 97.411 (2)° V = 1602.80 (12) Å3 Z = 4 Mo Kα radiation μ = 2.89 mm−1 T = 150 K 0.80 × 0.75 × 0.34 mm

Data collection

Bruker SMART 1000 CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.165, T max = 0.376 13470 measured reflections 3816 independent reflections 3462 reflections with I > 2σ(I) R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.019 wR(F 2) = 0.047 S = 1.03 3816 reflections 183 parameters H-atom parameters constrained Δρmax = 0.39 e Å−3 Δρmin = −0.21 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs. Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902159X/jh2078sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680902159X/jh2078Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H18Cl2N+·Br−F(000) = 760
Mr = 375.12Dx = 1.555 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8351 reflections
a = 11.9427 (5) Åθ = 2.3–28.7°
b = 8.9771 (4) ŵ = 2.89 mm−1
c = 15.0759 (6) ÅT = 150 K
β = 97.411 (2)°Block, colourless
V = 1602.80 (12) Å30.80 × 0.75 × 0.34 mm
Z = 4
Bruker SMART 1000 CCD diffractometer3816 independent reflections
Radiation source: sealed tube3462 reflections with I > 2σ(I)
graphiteRint = 0.015
ω rotation with narrow frames scansθmax = 28.8°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −15→15
Tmin = 0.165, Tmax = 0.376k = −11→11
13470 measured reflectionsl = −19→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.019Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0215P)2 + 0.7575P] where P = (Fo2 + 2Fc2)/3
3816 reflections(Δ/σ)max = 0.001
183 parametersΔρmax = 0.39 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
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.
xyzUiso*/Ueq
C10.35722 (11)0.30048 (15)0.05726 (9)0.0197 (3)
C20.45188 (11)0.20813 (15)0.06312 (9)0.0215 (3)
Cl10.48415 (3)0.09081 (4)0.15526 (2)0.02628 (8)
C30.52466 (12)0.20869 (18)−0.00141 (10)0.0280 (3)
H30.58860.14490.00420.034*
C40.50319 (14)0.30335 (19)−0.07430 (10)0.0329 (3)
H40.55170.3031−0.11950.039*
C50.41118 (14)0.39814 (19)−0.08124 (10)0.0326 (3)
H50.39670.4632−0.13110.039*
C60.33996 (12)0.39827 (17)−0.01548 (10)0.0259 (3)
H60.27840.4660−0.01990.031*
C70.27893 (11)0.30423 (14)0.12803 (9)0.0184 (3)
H7A0.26040.40930.13970.022*
H7B0.31910.26260.18410.022*
N10.16846 (9)0.21772 (12)0.10372 (7)0.0172 (2)
C80.19294 (12)0.05980 (15)0.08053 (10)0.0231 (3)
H8A0.23670.05850.02980.035*
H8B0.12170.00620.06440.035*
H8C0.23640.01140.13220.035*
C90.09604 (12)0.28868 (16)0.02635 (9)0.0226 (3)
H9A0.02240.23890.01710.034*
H9B0.13300.2791−0.02780.034*
H9C0.08540.39440.03920.034*
C100.10924 (11)0.22455 (16)0.18762 (9)0.0201 (3)
H10A0.15970.18040.23800.024*
H10B0.09750.33040.20240.024*
C11−0.00317 (11)0.14542 (16)0.17982 (9)0.0201 (3)
C12−0.10616 (12)0.22153 (16)0.16489 (9)0.0221 (3)
Cl2−0.10838 (3)0.41433 (4)0.15277 (2)0.02902 (8)
C13−0.20899 (12)0.14761 (19)0.16070 (10)0.0287 (3)
H13−0.27770.20190.15030.034*
C14−0.21075 (13)−0.00522 (19)0.17171 (10)0.0306 (3)
H14−0.2808−0.05650.16790.037*
C15−0.11021 (13)−0.08362 (18)0.18827 (10)0.0288 (3)
H15−0.1113−0.18850.19640.035*
C16−0.00792 (12)−0.00860 (17)0.19297 (9)0.0244 (3)
H160.0605−0.06320.20540.029*
Br10.332790 (12)0.178154 (15)0.376859 (9)0.02633 (5)
U11U22U33U12U13U23
C10.0179 (6)0.0197 (6)0.0211 (6)−0.0019 (5)0.0009 (5)−0.0006 (5)
C20.0199 (6)0.0226 (7)0.0212 (6)0.0005 (5)0.0000 (5)−0.0001 (5)
Cl10.02153 (16)0.02815 (18)0.02852 (17)0.00756 (13)0.00083 (13)0.00558 (14)
C30.0215 (7)0.0344 (8)0.0284 (7)0.0010 (6)0.0042 (6)−0.0048 (6)
C40.0314 (8)0.0444 (9)0.0244 (7)−0.0066 (7)0.0096 (6)−0.0029 (7)
C50.0354 (8)0.0375 (9)0.0244 (7)−0.0061 (7)0.0024 (6)0.0081 (6)
C60.0234 (7)0.0258 (7)0.0275 (7)−0.0007 (6)−0.0003 (6)0.0057 (6)
C70.0163 (6)0.0182 (6)0.0200 (6)0.0006 (5)−0.0003 (5)−0.0012 (5)
N10.0153 (5)0.0179 (5)0.0179 (5)0.0021 (4)0.0006 (4)−0.0008 (4)
C80.0222 (7)0.0174 (6)0.0306 (7)0.0005 (5)0.0072 (5)−0.0040 (5)
C90.0206 (7)0.0279 (7)0.0178 (6)0.0025 (5)−0.0032 (5)0.0017 (5)
C100.0163 (6)0.0274 (7)0.0165 (6)0.0027 (5)0.0012 (5)−0.0019 (5)
C110.0174 (6)0.0280 (7)0.0150 (6)0.0026 (5)0.0019 (5)−0.0012 (5)
C120.0200 (7)0.0278 (7)0.0180 (6)0.0038 (5)0.0011 (5)−0.0033 (5)
Cl20.02630 (17)0.02741 (18)0.03270 (19)0.00973 (14)0.00138 (14)−0.00288 (14)
C130.0171 (7)0.0423 (9)0.0265 (7)0.0025 (6)0.0022 (5)−0.0050 (6)
C140.0232 (7)0.0420 (9)0.0272 (7)−0.0083 (6)0.0058 (6)−0.0055 (6)
C150.0348 (8)0.0288 (8)0.0244 (7)−0.0035 (6)0.0098 (6)−0.0008 (6)
C160.0238 (7)0.0289 (7)0.0210 (7)0.0053 (6)0.0056 (5)0.0026 (6)
Br10.02822 (8)0.02006 (7)0.02794 (8)−0.00575 (5)−0.00691 (5)0.00494 (5)
C1—C21.3955 (19)C9—H9A0.9800
C1—C61.3990 (19)C9—H9B0.9800
C1—C71.5068 (18)C9—H9C0.9800
C2—C31.386 (2)C10—C111.5100 (18)
C2—Cl11.7463 (14)C10—H10A0.9900
C3—C41.387 (2)C10—H10B0.9900
C3—H30.9500C11—C161.399 (2)
C4—C51.383 (2)C11—C121.3995 (18)
C4—H40.9500C12—C131.390 (2)
C5—C61.387 (2)C12—Cl21.7403 (15)
C5—H50.9500C13—C141.382 (2)
C6—H60.9500C13—H130.9500
C7—N11.5341 (16)C14—C151.386 (2)
C7—H7A0.9900C14—H140.9500
C7—H7B0.9900C15—C161.389 (2)
N1—C81.4979 (16)C15—H150.9500
N1—C91.5014 (16)C16—H160.9500
N1—C101.5279 (16)Br1—N14.3416 (11)
C8—H8A0.9800Br1—N1i4.1439 (11)
C8—H8B0.9800Br1—N1ii4.8527 (11)
C8—H8C0.9800Br1—N1iii5.0105 (11)
C2—C1—C6117.29 (13)N1—C8—H8C109.5
C2—C1—C7122.68 (12)H8A—C8—H8C109.5
C6—C1—C7119.92 (12)H8B—C8—H8C109.5
C3—C2—C1122.00 (13)N1—C9—H9A109.5
C3—C2—Cl1117.81 (11)N1—C9—H9B109.5
C1—C2—Cl1120.17 (10)H9A—C9—H9B109.5
C2—C3—C4119.33 (14)N1—C9—H9C109.5
C2—C3—H3120.3H9A—C9—H9C109.5
C4—C3—H3120.3H9B—C9—H9C109.5
C5—C4—C3120.07 (14)C11—C10—N1114.74 (10)
C5—C4—H4120.0C11—C10—H10A108.6
C3—C4—H4120.0N1—C10—H10A108.6
C4—C5—C6120.05 (14)C11—C10—H10B108.6
C4—C5—H5120.0N1—C10—H10B108.6
C6—C5—H5120.0H10A—C10—H10B107.6
C5—C6—C1121.19 (14)C16—C11—C12117.03 (13)
C5—C6—H6119.4C16—C11—C10120.39 (12)
C1—C6—H6119.4C12—C11—C10122.47 (13)
C1—C7—N1114.37 (10)C13—C12—C11121.81 (14)
C1—C7—H7A108.7C13—C12—Cl2117.94 (11)
N1—C7—H7A108.7C11—C12—Cl2120.24 (11)
C1—C7—H7B108.7C14—C13—C12119.69 (14)
N1—C7—H7B108.7C14—C13—H13120.2
H7A—C7—H7B107.6C12—C13—H13120.2
C8—N1—C9109.29 (10)C13—C14—C15119.95 (14)
C8—N1—C10110.88 (10)C13—C14—H14120.0
C9—N1—C10110.14 (10)C15—C14—H14120.0
C8—N1—C7110.31 (10)C14—C15—C16119.92 (14)
C9—N1—C7111.24 (10)C14—C15—H15120.0
C10—N1—C7104.93 (9)C16—C15—H15120.0
N1—C8—H8A109.5C15—C16—C11121.57 (13)
N1—C8—H8B109.5C15—C16—H16119.2
H8A—C8—H8B109.5C11—C16—H16119.2
C6—C1—C2—C3−2.0 (2)C8—N1—C10—C11−60.79 (14)
C7—C1—C2—C3−178.34 (13)C9—N1—C10—C1160.32 (15)
C6—C1—C2—Cl1176.20 (11)C7—N1—C10—C11−179.87 (11)
C7—C1—C2—Cl1−0.19 (18)N1—C10—C11—C1682.49 (15)
C1—C2—C3—C4−0.1 (2)N1—C10—C11—C12−101.51 (15)
Cl1—C2—C3—C4−178.34 (12)C16—C11—C12—C13−1.8 (2)
C2—C3—C4—C51.3 (2)C10—C11—C12—C13−177.91 (13)
C3—C4—C5—C6−0.3 (2)C16—C11—C12—Cl2177.16 (10)
C4—C5—C6—C1−2.0 (2)C10—C11—C12—Cl21.03 (18)
C2—C1—C6—C53.0 (2)C11—C12—C13—C140.2 (2)
C7—C1—C6—C5179.49 (13)Cl2—C12—C13—C14−178.79 (12)
C2—C1—C7—N1−101.76 (14)C12—C13—C14—C151.0 (2)
C6—C1—C7—N181.94 (15)C13—C14—C15—C16−0.6 (2)
C1—C7—N1—C855.23 (14)C14—C15—C16—C11−1.1 (2)
C1—C7—N1—C9−66.23 (14)C12—C11—C16—C152.2 (2)
C1—C7—N1—C10174.70 (11)C10—C11—C16—C15178.46 (12)
D—H···AD—HH···AD···AD—H···A
C6—H6···Cl2iv0.952.873.6451 (15)140
C9—H9A···Br1v0.982.993.6365 (13)125
C9—H9C···Br1ii0.982.953.8414 (15)151
C7—H7A···Br1ii0.992.663.6095 (13)162
C7—H7B···Br10.992.993.8916 (13)152
C10—H10A···Br10.992.753.6709 (13)156
C16—H16···Br1i0.952.993.7361 (14)136
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C6—H6⋯Cl2i0.952.873.6451 (15)140
C9—H9A⋯Br1ii0.982.993.6365 (13)125
C9—H9C⋯Br1iii0.982.953.8414 (15)151
C7—H7A⋯Br1iii0.992.663.6095 (13)162
C7—H7B⋯Br10.992.993.8916 (13)152
C10—H10A⋯Br10.992.753.6709 (13)156
C16—H16⋯Br1iv0.952.993.7361 (14)136

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

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