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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2599
https://doi.org/10.1107/S1600536811032612

Tetra-n-butyl­ammonium bromide: a redetermination at 150 K addressing the merohedral twinning

Mark R. J. Elsegooda*

aChemistry Department, Loughborough University, Loughborough, LE11 3TU, England
*Correspondence e-mail: m.r.j.elsegood@lboro.ac.uk

(Received 4 August 2011; accepted 11 August 2011; online 14 September 2011)

The redetermined, low temperature (150 K), structure of tetra-n-butyl­ammonium bromide, (C4H9)4N+·Br−, has been found to be merohedrally twinned via twin law −1 0 0, 0 − 1 0, 1 0 1. The structure was previously determined, with low precision, no inclusion of H atoms and only the bromide ion refined with anisotropic displacement parameters, by Wang et al. (1995[Wang, Q., Habenschuss, A., Xenopoulos, A. & Wunderlich, B. (1995). Mol. Cryst. Liq. Cryst. Sci. Tech. A, 264, 115-129.]). Mol. Cryst. Liq. Cryst. Sci. Tech. A, 264, 115–129. The redetermined structure has considerably improved precision in all geometrical parameters, has all non-H atoms refined anisotropically, H atoms included, and is isomorphous with the iodide analogue. The structure is otherwise routine, with the shortest cation to anion contacts being between the bromide anion and the CH atoms close to the ammonium nitro­gen centre at a distance of ca. 2.98–3.11 Å. Each anion makes eight such contacts to four different anions. The n-butyl chains are fully extended, adopting an all-anti conformation with approximate S4 point symmetry.

Related literature

The structure was previously determined by Wang et al. (1995[Wang, Q., Habenschuss, A., Xenopoulos, A. & Wunderlich, B. (1995). Mol. Cryst. Liq. Cryst. Sci. Tech. A, 264, 115-129.]). For the uses of tetra-n-alkyl­ammonium salts and the isomorphous structure of tetra-n-butyl ammonium iodide, see: Prukała et al. (2007[Prukała, W., Marciniec, B. & Kubicki, M. (2007). Acta Cryst. E63, o1464-o1466.]). For a related stucture, see: McMullan & Jeffrey (1959[McMullan, R. & Jeffrey, G. A. (1959). J. Chem. Phys. 31, 1231-1234.]). For the conformation of n-butyl chains, see: Alder et al. (1990[Alder, R. W., Maunder, C. M. & Orpen, G. (1990). Tetrahedron Lett. 31, 6717-6720.]). For details of the Cambridge Structural Database, see: Fletcher et al. (1996[Fletcher, D. A., McMeeking, R. F. & Parkin, D. (1996). J. Chem. Inf. Comput. Sci. 36, 746-749.]); Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data

  • C16H36N+·Br−

  • Mr = 322.37

  • Monoclinic, C 2/c

  • a = 13.9773 (9) Å

  • b = 13.8623 (9) Å

  • c = 20.0450 (14) Å

  • β = 110.383 (10)°

  • V = 3640.7 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 2.25 mm−1

  • T = 150 K

  • 0.41 × 0.31 × 0.16 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.459, Tmax = 0.715

  • 21135 measured reflections

  • 5485 independent reflections

  • 4415 reflections with I > 2σ(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.073

  • S = 1.04

  • 5485 reflections

  • 168 parameters

  • H-atom parameters constrained

  • Δρmax = 0.62 e Å−3

  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). SAINT and APEX2. Bruker AXS Inc., Madison, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SAINT and APEX2. Bruker AXS Inc., Madison, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); molecular graphics: SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811032612/rn2089sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811032612/rn2089Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811032612/rn2089Isup3.cml

checkCIF report


Comment top

While many common reagents have had their crystal structures well determined, some many times, some deliberatly and many by accident, no good quality structure was available for the title compound, tetra-n-butylammonium bromide (I). Compound (I) is used in a number of synthesis applications (see Prukała et al., 2007, and references therein for further details) and as a source of the large tetra-n-butylammonium cation, which is useful in crystallizing large anions. A search of the Cambridge Structural Database (version 5.32 + 3 updates, Fletcher, et al., 1996, Allen, 2002) revealed just one reported structure of this compound with an R1 of 0.098 that had clearly been problematic (Wang et al., 1995). This earlier determination had only the bromide ion refined anisotropically and did not include hydrogen atoms in the model. The authors ruled out dynamic disorder as the cause of the difficulties and concluded that static disorder was the causeof the poor residual.

The crystals of (I) formed readily by vapour diffusion of diethyl ether into an acetonitrile solution. The data collection set-up was trouble free. After data reduction the structure did not solve readily with SHELXS (Sheldrick, 2008a); only the bromide, the nitrogen and two n-butyl chains being evident. When the structure failed to develop, the coordinates from the published structure were used as a starting point (Wang et al., 1995), but the R1 was ca. 35% for an isotropic model with all non-H atoms in the model. Twinning was suspected and confirmed by the TWINROTMAT routine in PLATON (Spek, 2009). Application of the merohedral twin law -1 0 0, 0 -1 0, 1 0 1, led to a reduction in R1 to ca. 5.0% at the same, isotropic, stage of refinement. Anisotropic refinement, and addition of H atoms, led to a good final R1 <3% with no adverse indicators. The ratio of major to minor twin components is 60.69: 39.31 (7)%

The structure is isomorphous with that of the iodide analogue described in detail recently (Prukała et al., 2007). The n-butyl chains are fully extended adopting an all-anti conformation with approximate S4 point symmetry (Alder et al., 1990). The bromide anion resides in a pocket between four cations, making four pairs of weak C—H···Br contacts in the range 2.98–3.11 Å to methylene hydrogens located one or two carbon atoms from the nitrogen cationic centre. The structures of the chloride and fluoride analogues have not been determined to date, although the unit cell of the hydrate of the chloride has been reported (McMullan & Jeffrey, 1959).

Related literature top

The structure was previously determined by Wang et al. (1995). For the uses of tetra-n-alkylammonium salts and the isomorphous structure of tetra-n-butyl ammonium iodide, see: Prukała et al. (2007). For a related stucture, see: McMullan & Jeffrey (1959). For the conformation of n-butyl chains, see: Alder et al. (1990). For details of the Cambridge Structural Database, see: Fletcher et al. (1996); Allen (2002).

Experimental top

The title compound (I) was used as received and crystallized from an acetonitrile solution via vapour diffusion with diethylether to give colourless blocks.

Refinement top

H atoms were included in a riding model with constrained bond lengths: for CH2 = 0.99 and CH3 = 0.98 Å with Uiso(H) = 1.2 Ueq(CH2) and =1.5Ueq(CH3).

Structure description top

While many common reagents have had their crystal structures well determined, some many times, some deliberatly and many by accident, no good quality structure was available for the title compound, tetra-n-butylammonium bromide (I). Compound (I) is used in a number of synthesis applications (see Prukała et al., 2007, and references therein for further details) and as a source of the large tetra-n-butylammonium cation, which is useful in crystallizing large anions. A search of the Cambridge Structural Database (version 5.32 + 3 updates, Fletcher, et al., 1996, Allen, 2002) revealed just one reported structure of this compound with an R1 of 0.098 that had clearly been problematic (Wang et al., 1995). This earlier determination had only the bromide ion refined anisotropically and did not include hydrogen atoms in the model. The authors ruled out dynamic disorder as the cause of the difficulties and concluded that static disorder was the causeof the poor residual.

The crystals of (I) formed readily by vapour diffusion of diethyl ether into an acetonitrile solution. The data collection set-up was trouble free. After data reduction the structure did not solve readily with SHELXS (Sheldrick, 2008a); only the bromide, the nitrogen and two n-butyl chains being evident. When the structure failed to develop, the coordinates from the published structure were used as a starting point (Wang et al., 1995), but the R1 was ca. 35% for an isotropic model with all non-H atoms in the model. Twinning was suspected and confirmed by the TWINROTMAT routine in PLATON (Spek, 2009). Application of the merohedral twin law -1 0 0, 0 -1 0, 1 0 1, led to a reduction in R1 to ca. 5.0% at the same, isotropic, stage of refinement. Anisotropic refinement, and addition of H atoms, led to a good final R1 <3% with no adverse indicators. The ratio of major to minor twin components is 60.69: 39.31 (7)%

The structure is isomorphous with that of the iodide analogue described in detail recently (Prukała et al., 2007). The n-butyl chains are fully extended adopting an all-anti conformation with approximate S4 point symmetry (Alder et al., 1990). The bromide anion resides in a pocket between four cations, making four pairs of weak C—H···Br contacts in the range 2.98–3.11 Å to methylene hydrogens located one or two carbon atoms from the nitrogen cationic centre. The structures of the chloride and fluoride analogues have not been determined to date, although the unit cell of the hydrate of the chloride has been reported (McMullan & Jeffrey, 1959).

The structure was previously determined by Wang et al. (1995). For the uses of tetra-n-alkylammonium salts and the isomorphous structure of tetra-n-butyl ammonium iodide, see: Prukała et al. (2007). For a related stucture, see: McMullan & Jeffrey (1959). For the conformation of n-butyl chains, see: Alder et al. (1990). For details of the Cambridge Structural Database, see: Fletcher et al. (1996); Allen (2002).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b) and PLATON (Spek, 2009); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b) and local programs.

Figures top
[Figure 1] Fig. 1. The asymmetric unit in the structure of (I) with displacement ellipsoids drawn at the 50% probability level.
Tetra-n-butylammonium bromide top
Crystal data top
C16H36N+·Br−F(000) = 1392
Mr = 322.37Dx = 1.176 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7468 reflections
a = 13.9773 (9) Åθ = 2.6–30.1°
b = 13.8623 (9) ŵ = 2.25 mm−1
c = 20.0450 (14) ÅT = 150 K
β = 110.383 (10)°Block, colourless
V = 3640.7 (4) Å30.41 × 0.31 × 0.16 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer		5485 independent reflections
Radiation source: fine-focus sealed tube4415 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω rotation with narrow frames scansθmax = 30.5°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)		h = −19→19
Tmin = 0.459, Tmax = 0.715k = −18→19
21135 measured reflectionsl = −28→28
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0379P)2 + 0.7322P]
where P = (Fo2 + 2Fc2)/3
5485 reflections(Δ/σ)max = 0.001
168 parametersΔρmax = 0.62 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C16H36N+·Br−V = 3640.7 (4) Å3
Mr = 322.37Z = 8
Monoclinic, C2/cMo Kα radiation
a = 13.9773 (9) ŵ = 2.25 mm−1
b = 13.8623 (9) ÅT = 150 K
c = 20.0450 (14) Å0.41 × 0.31 × 0.16 mm
β = 110.383 (10)°
Data collection top
Bruker APEXII CCD
diffractometer		5485 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)		4415 reflections with I > 2σ(I)
Tmin = 0.459, Tmax = 0.715Rint = 0.029
21135 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.073H-atom parameters constrained
S = 1.04Δρmax = 0.62 e Å−3
5485 reflectionsΔρmin = −0.24 e Å−3
168 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.737682 (14)0.00074 (2)0.475441 (8)0.03037 (6)
N10.49621 (18)0.25167 (8)0.49516 (13)0.0172 (2)
C10.44659 (14)0.30519 (13)0.54096 (10)0.0195 (4)
H1A0.49270.35790.56640.023*
H1B0.38260.33520.50930.023*
C20.4221 (2)0.24346 (12)0.59514 (15)0.0252 (6)
H2A0.48480.21050.62580.030*
H2B0.37180.19340.57020.030*
C30.37887 (16)0.30443 (14)0.64107 (11)0.0253 (4)
H3A0.31870.34060.61010.030*
H3B0.43090.35190.66820.030*
C40.3476 (3)0.24244 (16)0.69282 (16)0.0302 (6)
H4A0.29840.19360.66630.045*
H4B0.31630.28330.71940.045*
H4C0.40810.21060.72610.045*
C50.42140 (14)0.17734 (13)0.45040 (10)0.0191 (4)
H5A0.40850.12920.48270.023*
H5B0.35590.21010.42490.023*
C60.45519 (19)0.12433 (12)0.39615 (10)0.0230 (4)
H6A0.52080.09110.42060.028*
H6B0.46590.17120.36210.028*
C70.37484 (16)0.05075 (14)0.35601 (11)0.0259 (4)
H7A0.36130.00650.39050.031*
H7B0.31040.08470.32960.031*
C80.4089 (3)−0.00752 (19)0.30414 (11)0.0347 (5)
H8A0.41950.03580.26870.052*
H8B0.3563−0.05510.28010.052*
H8C0.4729−0.04090.33010.052*
C90.59273 (14)0.19965 (13)0.54137 (10)0.0202 (4)
H9A0.57290.14620.56660.024*
H9B0.62620.17080.50990.024*
C100.6700 (2)0.26295 (15)0.59616 (14)0.0253 (5)
H10A0.69170.31630.57180.030*
H10B0.63820.29140.62870.030*
C110.76246 (15)0.20341 (15)0.63871 (12)0.0291 (4)
H11A0.79140.17150.60580.035*
H11B0.74120.15260.66530.035*
C120.8439 (3)0.26686 (18)0.69083 (16)0.0365 (6)
H12A0.86370.31810.66460.055*
H12B0.90370.22750.71630.055*
H12C0.81650.29570.72510.055*
C130.52549 (14)0.32450 (13)0.44859 (10)0.0200 (4)
H13A0.57010.37410.47980.024*
H13B0.56590.29080.42380.024*
C140.43636 (18)0.37509 (13)0.39317 (10)0.0241 (4)
H14A0.39600.41080.41710.029*
H14B0.39120.32670.36110.029*
C150.47602 (16)0.44495 (14)0.35002 (11)0.0263 (4)
H15A0.51390.40860.32470.032*
H15B0.52380.49120.38260.032*
C160.3885 (3)0.5001 (2)0.29610 (10)0.0343 (5)
H16A0.34450.45490.26130.051*
H16B0.41620.54770.27160.051*
H16C0.34860.53320.32090.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02772 (9)0.02330 (8)0.04278 (10)0.00074 (10)0.01565 (8)0.0010 (2)
N10.0158 (9)0.0157 (5)0.0192 (6)−0.0003 (5)0.0048 (12)0.0008 (7)
C10.0217 (9)0.0173 (8)0.0213 (9)0.0011 (7)0.0099 (8)−0.0019 (7)
C20.0345 (15)0.0197 (10)0.0255 (12)−0.0008 (7)0.0157 (11)0.0002 (7)
C30.0274 (10)0.0261 (9)0.0271 (10)0.0023 (8)0.0154 (8)0.0008 (8)
C40.0316 (15)0.0361 (12)0.0308 (12)0.0011 (9)0.0208 (14)0.0059 (10)
C50.0177 (9)0.0181 (8)0.0221 (10)−0.0031 (6)0.0076 (7)−0.0022 (7)
C60.0215 (10)0.0229 (8)0.0251 (9)−0.0023 (8)0.0088 (9)−0.0047 (6)
C70.0289 (10)0.0219 (9)0.0284 (10)−0.0029 (8)0.0117 (8)−0.0061 (8)
C80.0435 (15)0.0270 (10)0.0368 (9)−0.0008 (11)0.0182 (12)−0.0112 (11)
C90.0189 (9)0.0189 (8)0.0223 (9)0.0029 (7)0.0067 (7)0.0004 (7)
C100.0218 (12)0.0236 (9)0.0254 (12)−0.0009 (8)0.0017 (10)0.0011 (8)
C110.0193 (9)0.0299 (10)0.0341 (11)0.0015 (8)0.0042 (8)−0.0038 (9)
C120.0218 (13)0.0513 (16)0.0310 (12)−0.0006 (13)0.0026 (11)−0.0076 (12)
C130.0227 (10)0.0169 (8)0.0227 (10)−0.0026 (7)0.0108 (8)0.0013 (7)
C140.0247 (11)0.0243 (8)0.0252 (9)0.0029 (8)0.0109 (9)0.0057 (7)
C150.0291 (10)0.0222 (9)0.0276 (11)−0.0012 (8)0.0100 (8)0.0037 (8)
C160.0371 (15)0.0302 (8)0.0319 (8)0.0019 (11)0.0073 (9)0.0101 (14)
Geometric parameters (Å, º) top
N1—C51.519 (3)C8—H8B0.9800
N1—C11.522 (3)C8—H8C0.9800
N1—C131.524 (3)C9—C101.522 (3)
N1—C91.526 (3)C9—H9A0.9900
C1—C21.513 (3)C9—H9B0.9900
C1—H1A0.9900C10—C111.520 (3)
C1—H1B0.9900C10—H10A0.9900
C2—C31.521 (3)C10—H10B0.9900
C2—H2A0.9900C11—C121.527 (4)
C2—H2B0.9900C11—H11A0.9900
C3—C41.523 (4)C11—H11B0.9900
C3—H3A0.9900C12—H12A0.9800
C3—H3B0.9900C12—H12B0.9800
C4—H4A0.9800C12—H12C0.9800
C4—H4B0.9800C13—C141.521 (3)
C4—H4C0.9800C13—H13A0.9900
C5—C61.518 (3)C13—H13B0.9900
C5—H5A0.9900C14—C151.526 (3)
C5—H5B0.9900C14—H14A0.9900
C6—C71.523 (3)C14—H14B0.9900
C6—H6A0.9900C15—C161.526 (3)
C6—H6B0.9900C15—H15A0.9900
C7—C81.518 (3)C15—H15B0.9900
C7—H7A0.9900C16—H16A0.9800
C7—H7B0.9900C16—H16B0.9800
C8—H8A0.9800C16—H16C0.9800
C5—N1—C1108.81 (17)C7—C8—H8C109.5
C5—N1—C13111.35 (18)H8A—C8—H8C109.5
C1—N1—C13108.81 (12)H8B—C8—H8C109.5
C5—N1—C9108.62 (12)C10—C9—N1114.89 (16)
C1—N1—C9110.88 (17)C10—C9—H9A108.5
C13—N1—C9108.39 (18)N1—C9—H9A108.5
C2—C1—N1114.96 (15)C10—C9—H9B108.5
C2—C1—H1A108.5N1—C9—H9B108.5
N1—C1—H1A108.5H9A—C9—H9B107.5
C2—C1—H1B108.5C11—C10—C9110.05 (17)
N1—C1—H1B108.5C11—C10—H10A109.7
H1A—C1—H1B107.5C9—C10—H10A109.7
C1—C2—C3110.93 (15)C11—C10—H10B109.7
C1—C2—H2A109.5C9—C10—H10B109.7
C3—C2—H2A109.5H10A—C10—H10B108.2
C1—C2—H2B109.5C10—C11—C12110.9 (2)
C3—C2—H2B109.5C10—C11—H11A109.5
H2A—C2—H2B108.0C12—C11—H11A109.5
C2—C3—C4111.53 (18)C10—C11—H11B109.5
C2—C3—H3A109.3C12—C11—H11B109.5
C4—C3—H3A109.3H11A—C11—H11B108.1
C2—C3—H3B109.3C11—C12—H12A109.5
C4—C3—H3B109.3C11—C12—H12B109.5
H3A—C3—H3B108.0H12A—C12—H12B109.5
C3—C4—H4A109.5C11—C12—H12C109.5
C3—C4—H4B109.5H12A—C12—H12C109.5
H4A—C4—H4B109.5H12B—C12—H12C109.5
C3—C4—H4C109.5C14—C13—N1115.22 (17)
H4A—C4—H4C109.5C14—C13—H13A108.5
H4B—C4—H4C109.5N1—C13—H13A108.5
C6—C5—N1115.45 (17)C14—C13—H13B108.5
C6—C5—H5A108.4N1—C13—H13B108.5
N1—C5—H5A108.4H13A—C13—H13B107.5
C6—C5—H5B108.4C13—C14—C15109.86 (18)
N1—C5—H5B108.4C13—C14—H14A109.7
H5A—C5—H5B107.5C15—C14—H14A109.7
C5—C6—C7110.28 (19)C13—C14—H14B109.7
C5—C6—H6A109.6C15—C14—H14B109.7
C7—C6—H6A109.6H14A—C14—H14B108.2
C5—C6—H6B109.6C14—C15—C16111.1 (2)
C7—C6—H6B109.6C14—C15—H15A109.4
H6A—C6—H6B108.1C16—C15—H15A109.4
C8—C7—C6111.6 (2)C14—C15—H15B109.4
C8—C7—H7A109.3C16—C15—H15B109.4
C6—C7—H7A109.3H15A—C15—H15B108.0
C8—C7—H7B109.3C15—C16—H16A109.5
C6—C7—H7B109.3C15—C16—H16B109.5
H7A—C7—H7B108.0H16A—C16—H16B109.5
C7—C8—H8A109.5C15—C16—H16C109.5
C7—C8—H8B109.5H16A—C16—H16C109.5
H8A—C8—H8B109.5H16B—C16—H16C109.5
C5—N1—C1—C263.9 (2)C5—N1—C9—C10−172.7 (2)
C13—N1—C1—C2−174.6 (2)C1—N1—C9—C10−53.2 (2)
C9—N1—C1—C2−55.5 (2)C13—N1—C9—C1066.2 (2)
N1—C1—C2—C3176.5 (2)N1—C9—C10—C11−179.95 (19)
C1—C2—C3—C4176.5 (2)C9—C10—C11—C12176.4 (2)
C1—N1—C5—C6174.16 (17)C5—N1—C13—C1454.1 (2)
C13—N1—C5—C654.2 (2)C1—N1—C13—C14−65.8 (2)
C9—N1—C5—C6−65.0 (2)C9—N1—C13—C14173.53 (16)
N1—C5—C6—C7178.84 (17)N1—C13—C14—C15−179.49 (17)
C5—C6—C7—C8−176.82 (18)C13—C14—C15—C16−177.50 (18)

Experimental details

Crystal data
Chemical formulaC16H36N+·Br−
Mr322.37
Crystal system, space groupMonoclinic, C2/c
Temperature (K)150
a, b, c (Å)13.9773 (9), 13.8623 (9), 20.0450 (14)
β (°) 110.383 (10)
V (Å3)3640.7 (4)
Z8
Radiation typeMo Kα
µ (mm−1)2.25
Crystal size (mm)0.41 × 0.31 × 0.16
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2008a)
Tmin, Tmax0.459, 0.715
No. of measured, independent and
observed [I > 2σ(I)] reflections		21135, 5485, 4415
Rint0.029
(sin θ/λ)max (Å−1)0.715
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.073, 1.04
No. of reflections5485
No. of parameters168
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.62, −0.24

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008b) and local programs.

 

Acknowledgements

We wish to acknowledge the use of the EPSRC's Chemical Database Service at Daresbury.

References

First citationAlder, R. W., Maunder, C. M. & Orpen, G. (1990). Tetrahedron Lett. 31, 6717–6720.  CrossRef CAS Web of Science Google Scholar
 First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationBruker (2008). SAINT and APEX2. Bruker AXS Inc., Madison, USA.  Google Scholar
 First citationFletcher, D. A., McMeeking, R. F. & Parkin, D. (1996). J. Chem. Inf. Comput. Sci. 36, 746–749.  CrossRef CAS Web of Science Google Scholar
 First citationMcMullan, R. & Jeffrey, G. A. (1959). J. Chem. Phys. 31, 1231–1234.  CSD CrossRef CAS Web of Science Google Scholar
 First citationPrukała, W., Marciniec, B. & Kubicki, M. (2007). Acta Cryst. E63, o1464–o1466.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008b). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, Q., Habenschuss, A., Xenopoulos, A. & Wunderlich, B. (1995). Mol. Cryst. Liq. Cryst. Sci. Tech. A, 264, 115–129.  CrossRef CAS Web of Science Google Scholar

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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2599
https://doi.org/10.1107/S1600536811032612
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