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Tetra­isohexyl­ammonium bromide [systematic name: tetra­kis­(4-methyl­pentyl)aza­nium bromide], C24H52N+·Br-, is a power­ful structure II clathrate hydrate crystal-growth inhibitor. The crystal structure, in the space group P3221, contains one ammonium cation and one bromide anion in the asymmetric unit, both on general positions. At 100 K, the ammonium cation exhibits one ordered isohexyl chain and three disordered isohexyl chains. At 250 K, all four isohexyl chains are disordered. In an effort to reduce the disorder in the alkyl chains, the crystal was thermally cycled, but the disorder remained, indicating that it is dynamic in nature.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112009377/bi3031sup1.cif
Contains datablocks I_100KQ, I_250K, I_100KC, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112009377/bi3031I_100KQsup2.hkl
Contains datablock I_100KQ

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112009377/bi3031I_250Ksup3.hkl
Contains datablock I_250K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112009377/bi3031I_100KCsup4.hkl
Contains datablock I_100KC

cdx

Chemdraw file https://doi.org/10.1107/S0108270112009377/bi3031I_100KQsup5.cdx
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270112009377/bi3031I_100KQsup6.cml
Supplementary material

CCDC references: 879437; 879438; 879439

Comment top

Gas hydrates are ice-like clathrates that are formed at high pressure and low temperature from water or water/hydrocarbon mixtures, and are a serious problem in the oil and gas industry due to their ability to cause blockages. Low-dosage hydrate inhibitors are a recent alternative to thermodynamic hydrate inhibitors and can be divided into two classes: kinetic inhibitors and anti-agglomerants. A major breakthrough in this area of research was the development of quaternary ammonium surfactant anti-agglomerants with tributyl or tripentyl head-groups (Kelland, 2006). Searches of the Cambridge Structural Database (CSD, Version 5.32 including November 2010 and February 2011 updates; Allen, 2002; Bruno et al., 2002) show that many quaternary ammonium halide structures have been reported, both as hydrate clathrates (e.g. Feil & Jeffrey, 1961; McMullan et al., 1963; Lipkowski et al., 1994, 2002; Shimada et al., 2005; Komarov et al., 2007; Wang et al., 2009) and without solvent as n-propyl (Yoshida et al., 1994), n-butyl (Wang et al., 1995; Prukała et al., 2007), n-pentyl (Szafranska et al., 2000), n-dodecyl, n-hexadecyl and n-octadecyl (Abdallah et al., 1999) ammonium halides. However, despite its industrial importance, the structure of the title compound, (I), has never been reported and, remarkably, the tetrakis(isohexyl)ammonium cation does not appear in the CSD at all. The most closely related compound is tetrakis(isopentyl) ammonium bromide, which is reported as the hydrate clathrate (Wang et al., 2009).

Compound (I), was found to form soft greasy soap-like crystals which gave poor-quality diffraction data and were consequently challenging to work with. Almost no diffraction was seen with a conventional Mo radiation X-ray source. However, reasonable data could be obtained using a Cu microfocus instrument. Initially, the chosen crystal was placed directly in a cold stream (Cosier & Glazer, 1986) at 100 K. The space group was determined to be P3221 and the structure was solved. Examination of the difference map indicated disorder in three of the four alkyl chains.

It is often postulated that rapid or `quench' cooling can cause dynamic motion to freeze in multiple disordered components to form a metastable structure, whereas slow cooling in such systems enables dynamic components to find a single global optimum position and achieve a more stable state. To test this in (I), the single crystal was warmed to 300 K and after a few minutes was cooled back to 250 K (at 120 K h-1), where data were collected. The crystal was then further cooled to 100 K (at 120 K h-1), where a third data collection was carried out for comparison. All three data collections were carried out in an identical manner and indexed on the same orientation matrix so that the first structure solution at 100 K could be used as the starting point for all refinements.

The structure consists of one ammonium cation and one bromide anion in the asymmetric unit (Fig. 1), both on general positions. Each bromide anion is surrounded by three cations, two of which are related by a twofold screw axis and the third related to the other two by a twofold rotor and a threefold screw axis, respectively (Fig. 2). Initially, each structure was refined without disorder and with anisotropic displacement parameters (ADPs) for each isohexyl group. The two structures at 100 K showed very little difference, so the disorder was modelled for the first 100 K data set and the model transferred to the other 100 K refinement. This model consisted of one ordered alkyl group (C11–C16), two where the terminal 3–5 atoms wagged (C31–C36 and C41–C46), and one where the end group wagged and is also rotated (C21–C26). On refinement against the data at 250 K, it was clear that the alkyl group that was ordered at 100 K (C11–C16) also appeared disordered. Although all of the ADPs increased in size between 100 and 250 K, the nature of the disorder showed little sign of change in the two wagging alkyl chains (C31–C36 and C41–C46; Fig. 3). A slight change in the orientation of the chain defined by atoms C21–C26 was observed. It is of note that the highest density of short contacts is between the minor component of the terminal methyl groups of this chain and their symmetry equivalents, suggesting that there is a correlation between the disorder in neighbouring molecules. At 250 K, there are additional contacts between the C21–C26 chain and the C11–C16 chain that is ordered at 100 K. It is possible, therefore, that the disorder seen in the C11–C16 chain at 250 K is correlated with increased motion in the C21–C26 chain.

In conclusion, in the case of this compound, the structure accessed by flash cooling to 100 K is the same as that achieved by a slower cooling regime. This suggests that the disorder at 100 K is dynamic in nature.

Related literature top

For related literature, see: Abdallah et al. (1999); Allen (2002); Betteridge et al. (2003); Bruno et al. (2002); Cooper et al. (2010); Cosier & Glazer (1986); Feil & Jeffrey (1961); Flack (1983); Flack & Bernardinelli (2000); Hooft et al. (2008); Kelland (2006); Komarov et al. (2007); Lipkowski et al. (1994, 2002); McMullan et al. (1963); Prukała et al. (2007); Shimada et al. (2005); Szafranska et al. (2000); Thompson & Watkin (2009, 2011); Wang et al. (1995, 2009); Yoshida et al. (1994).

Experimental top

Isohexyl bromide (3.96 g, 24 mmol), powdered K2CO3 (3.31 g, 24 mmol) and isohexylamine hydrochloride (1.00 g, 7.27 mmol) were refluxed in isobutyronitrile (20 ml) for 5 d. The solution was filtered and the solvent removed to leave an off-white solid (52% yield). Crystals were grown from an ethyl acetate–diethyl ether mixture (Solvent ratio?) cooled to 243 K over a period of 24 h. NMR data were recorded on a Varian 300 MHz instrument. 1H NMR (CDCl3, δ, p.p.m.): 0.92 (doublet, 6H), 1.31 (quartet, 2H), 1.66 (multiplet, 1H), 1.67 (multiplet, 2H), 3.39 (multiplet, 2H). 13C NMR (CDCl3, δ, p.p.m.): 20.14, 22.27, 27.44, 35.16, 59.45.

Refinement top

Analysis of the Flack x (Flack, 1983; Flack & Bernardinelli, 2000) and Hooft y parameters (Hooft et al., 2008) within CRYSTALS (Betteridge et al. 2003; Thompson & Watkin, 2009, 2011) indicated that the crystal had spontaneously resolved and was enantiopure in space group P3221. The disorder was modelled by splitting atoms with prolate anisotropic displacement parameters (ADPs) into two components; the naming convention used involved appending a 1 or 0 to the index number, such that C26 became C260 and C261 etc. To ensure a sensible geometry for the disordered model, the bond distances and angles along the isohexyl chains were restrained to be the same, with s.u. values of 0.01 Å and 0.1 °, respectively, and the ADPs of the disordered atoms were restrained to be similar, with an s.u. value of 0.01 Å2. The H atoms were generally visible in difference maps, but were positioned geometrically then initially refined with soft restraints, after which the positions were refined with riding constraints (Cooper et al., 2010).

Computing details top

For all compounds, data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure at 100 K after rapid (quench) cooling, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A partial packing diagram, viewed along the a axis, showing the symmetry relationships between the ammonium cations surrounding the bromide anion. The N1 cation (blue in the electronic version of the paper) is related to the N1i cation (red) by a 21 screw axis parallel to a, and related to the N1ii cation (orange) by a 32 screw axis parallel to c. The N1ii and N1i cations are related by a twofold rotation parallel to b. [Symmetry codes: (i) x - y + 1, -y + 1, -z + 4/3; (ii) -x + y + 1, -x + 1, z + 1/3.]
[Figure 3] Fig. 3. The molecular structure after slow cooling (a) to 250 K and (b) to 100 K, with displacement ellipsoids drawn at the 50% probability level.
(I_100KQ) tetrakis(4-methylpentyl)azanium bromide top
Crystal data top
C24H52N+·BrDx = 1.039 Mg m3
Mr = 434.59Cu Kα radiation, λ = 1.54184 Å
Trigonal, P3221Cell parameters from 47154 reflections
Hall symbol: P 32 2"θ = 3–76°
a = 15.12762 (13) ŵ = 2.04 mm1
c = 21.0223 (2) ÅT = 100 K
V = 4166.31 (6) Å3Plate, colourless
Z = 60.15 × 0.14 × 0.07 mm
F(000) = 1428
Data collection top
Oxford SuperNova Dual
diffractometer with Cu at zero and Atlas detector
5591 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 76.4°, θmin = 3.4°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
h = 1818
Tmin = 0.57, Tmax = 0.87k = 1919
89102 measured reflectionsl = 2626
5781 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041 Method = Modified Sheldrick w = 1/[σ2(F2) + (0.07P)2 + 1.86P],
where P = [max(Fo2,0) + 2Fc2]/3
wR(F2) = 0.114(Δ/σ)max = 0.002
S = 1.02Δρmax = 0.46 e Å3
5781 reflectionsΔρmin = 0.60 e Å3
347 parametersAbsolute structure: Flack (1983), with 2550 Friedel pairs
648 restraintsAbsolute structure parameter: 0.02 (2)
Primary atom site location: structure-invariant direct methods
Crystal data top
C24H52N+·BrZ = 6
Mr = 434.59Cu Kα radiation
Trigonal, P3221µ = 2.04 mm1
a = 15.12762 (13) ÅT = 100 K
c = 21.0223 (2) Å0.15 × 0.14 × 0.07 mm
V = 4166.31 (6) Å3
Data collection top
Oxford SuperNova Dual
diffractometer with Cu at zero and Atlas detector
5781 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
5591 reflections with I > 2σ(I)
Tmin = 0.57, Tmax = 0.87Rint = 0.033
89102 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.114Δρmax = 0.46 e Å3
S = 1.02Δρmin = 0.60 e Å3
5781 reflectionsAbsolute structure: Flack (1983), with 2550 Friedel pairs
347 parametersAbsolute structure parameter: 0.02 (2)
648 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br10.84883 (2)0.52844 (3)0.717967 (14)0.0586
N10.58314 (17)0.42813 (17)0.59778 (10)0.0477
C110.6075 (2)0.5377 (2)0.58712 (13)0.0444
C120.7107 (3)0.6197 (3)0.61083 (15)0.0522
C130.7231 (3)0.7247 (3)0.60029 (16)0.0575
C140.8319 (3)0.8127 (3)0.6049 (2)0.0693
C150.8375 (4)0.9134 (3)0.5887 (2)0.0865
C160.8813 (4)0.8186 (4)0.6674 (2)0.0882
C210.48075 (19)0.36059 (19)0.56525 (13)0.0497
C220.4396 (2)0.2465 (2)0.57012 (17)0.0639
C2300.3396 (6)0.1876 (3)0.5320 (3)0.08500.264 (6)
C2400.2447 (6)0.1109 (7)0.5701 (6)0.10480.264 (6)
C2500.1505 (9)0.0523 (12)0.5286 (9)0.09560.264 (6)
C2600.2639 (9)0.0385 (8)0.6111 (6)0.07360.264 (6)
C2310.3306 (3)0.1886 (3)0.5481 (2)0.06360.736 (6)
C2410.2840 (3)0.0730 (3)0.54182 (17)0.08070.736 (6)
C2510.1716 (5)0.0189 (4)0.5282 (4)0.11550.736 (6)
C2610.3419 (5)0.0424 (4)0.4931 (3)0.09850.736 (6)
C310.6669 (2)0.4119 (2)0.57056 (12)0.0533
C320.6922 (2)0.4401 (3)0.50165 (12)0.0573
C330.7771 (2)0.4205 (3)0.48023 (14)0.0715
C3400.7887 (7)0.4140 (9)0.4087 (3)0.09430.236 (13)
C3500.8913 (13)0.426 (2)0.3900 (4)0.10200.236 (13)
C3600.7658 (17)0.4868 (16)0.3711 (5)0.09470.236 (13)
C3410.8034 (3)0.4362 (4)0.41078 (19)0.08790.764 (13)
C3510.8835 (5)0.4080 (6)0.3922 (2)0.09750.764 (13)
C3610.8320 (7)0.5399 (6)0.3885 (3)0.10730.764 (13)
C410.57975 (19)0.4075 (3)0.66861 (12)0.0573
C4210.4945 (5)0.3997 (6)0.70202 (18)0.04950.464 (7)
C4310.4851 (4)0.3510 (4)0.7667 (2)0.05170.464 (7)
C4410.4190 (3)0.3635 (3)0.81380 (17)0.04870.464 (7)
C4510.4203 (5)0.3202 (7)0.8782 (3)0.06690.464 (7)
C4610.3112 (5)0.3226 (6)0.7903 (3)0.05430.464 (7)
C4200.5194 (5)0.4486 (6)0.71066 (19)0.05940.536 (7)
C4300.5004 (4)0.4036 (5)0.7773 (2)0.07840.536 (7)
C4400.4079 (4)0.2974 (5)0.7851 (2)0.08500.536 (7)
C4500.3975 (6)0.2552 (8)0.8526 (4)0.10240.536 (7)
C4600.3091 (5)0.2911 (7)0.7631 (4)0.08710.536 (7)
H1110.55410.54690.60650.0670*
H1120.60250.54590.54230.0656*
H1210.71550.60650.65660.0791*
H1220.76450.61330.58870.0793*
H1310.68710.73530.63560.0859*
H1320.69030.72640.56190.0854*
H1410.87190.80020.57370.1021*
H1510.90820.97030.59160.1558*
H1520.79660.92450.62080.1561*
H1530.80940.90980.54690.1558*
H1610.94930.87850.66650.1585*
H1620.84080.82560.70020.1589*
H1630.88580.75730.67350.1584*
H2110.43320.37660.58540.0742*
H2120.48710.38020.52050.0733*
H2210.42710.22640.61490.0902*0.264 (6)
H2220.48880.22970.55340.0899*0.264 (6)
H23010.32350.23610.51400.1172*0.264 (6)
H23020.34950.14940.49850.1172*0.264 (6)
H24010.23260.15230.60200.1391*0.264 (6)
H25010.11050.01780.54300.1700*0.264 (6)
H25020.11070.08560.53350.1701*0.264 (6)
H25030.16910.05400.48420.1700*0.264 (6)
H26010.24420.03970.65390.1409*0.264 (6)
H26020.33410.05670.61000.1408*0.264 (6)
H26030.22350.02840.59490.1410*0.264 (6)
H2230.44500.22880.61470.0902*0.736 (6)
H2240.47890.22690.54510.0894*0.736 (6)
H23110.29080.20580.57480.0886*0.736 (6)
H23120.32920.21100.50630.0890*0.736 (6)
H24110.28940.04660.58390.1099*0.736 (6)
H25110.14840.05250.51880.1930*0.736 (6)
H25120.13580.02160.56680.1931*0.736 (6)
H25130.15870.05060.49170.1930*0.736 (6)
H26110.31600.03100.49480.1651*0.736 (6)
H26120.41380.07770.50120.1653*0.736 (6)
H26130.33180.05990.45010.1652*0.736 (6)
H3110.72720.45180.59690.0777*
H3120.64350.33960.57640.0780*
H3210.71610.51220.49650.0830*
H3220.63170.40140.47520.0832*
H3310.84210.47350.49780.1010*0.236 (13)
H3320.76210.35430.49760.1011*0.236 (13)
H34010.73680.34460.39420.1250*0.236 (13)
H35010.87790.36620.35850.1659*0.236 (13)
H35020.93160.49790.36710.1659*0.236 (13)
H35030.92860.42400.43170.1660*0.236 (13)
H36010.83670.53800.34190.1620*0.236 (13)
H36020.75070.53050.40850.1620*0.236 (13)
H36030.69680.43740.34060.1620*0.236 (13)
H3330.84160.46860.50510.1010*0.764 (13)
H3340.75890.35050.49060.1016*0.764 (13)
H34110.73680.38950.38640.1232*0.764 (13)
H35110.89670.41890.34710.1669*0.764 (13)
H35120.94740.44790.41420.1670*0.764 (13)
H35130.85940.33680.40000.1667*0.764 (13)
H36110.86710.55250.34770.1837*0.764 (13)
H36120.87500.58940.41950.1838*0.764 (13)
H36130.76990.54300.38160.1842*0.764 (13)
H4110.64360.45930.68730.0839*0.464 (7)
H4120.57450.34090.67350.0838*0.464 (7)
H42110.50670.46780.70910.0752*0.464 (7)
H42120.43180.36230.67670.0760*0.464 (7)
H43110.55360.38280.78540.0761*0.464 (7)
H43120.46040.27910.75990.0761*0.464 (7)
H44110.44630.43580.81970.0746*0.464 (7)
H45110.36690.31920.90450.1207*0.464 (7)
H45120.48610.36290.89770.1210*0.464 (7)
H45130.40860.25210.87420.1211*0.464 (7)
H46110.27020.32950.82300.1047*0.464 (7)
H46120.28330.25190.77910.1044*0.464 (7)
H46130.31260.36070.75260.1047*0.464 (7)
H4130.65050.44050.68280.0835*0.536 (7)
H4140.54990.33430.67550.0837*0.536 (7)
H42010.56160.52150.71340.0850*0.536 (7)
H42020.45500.43270.69050.0847*0.536 (7)
H43010.48870.44840.80420.1051*0.536 (7)
H43020.56150.40370.79250.1050*0.536 (7)
H44010.42010.25330.75550.1143*0.536 (7)
H45010.36880.18280.85170.1669*0.536 (7)
H45020.35310.27060.87800.1667*0.536 (7)
H45030.46320.28610.87340.1669*0.536 (7)
H46010.26090.22140.75540.1480*0.536 (7)
H46020.28330.31720.79530.1482*0.536 (7)
H46030.32000.32830.72420.1479*0.536 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04245 (16)0.0880 (3)0.05031 (16)0.03637 (16)0.00008 (12)0.01638 (14)
N10.0437 (11)0.0563 (13)0.0508 (12)0.0309 (10)0.0004 (9)0.0086 (10)
C110.0480 (14)0.0549 (16)0.0416 (13)0.0342 (13)0.0053 (11)0.0013 (11)
C120.0562 (17)0.0582 (17)0.0512 (15)0.0353 (15)0.0122 (13)0.0032 (13)
C130.0645 (19)0.0551 (17)0.0604 (18)0.0355 (16)0.0192 (15)0.0097 (14)
C140.074 (2)0.061 (2)0.070 (2)0.0315 (18)0.0162 (18)0.0011 (17)
C150.103 (3)0.060 (2)0.088 (3)0.035 (2)0.035 (3)0.005 (2)
C160.082 (3)0.069 (2)0.100 (3)0.027 (2)0.040 (3)0.003 (2)
C210.0456 (13)0.0552 (14)0.0524 (13)0.0282 (11)0.0018 (11)0.0048 (11)
C220.0683 (19)0.0548 (16)0.0653 (17)0.0283 (15)0.0103 (16)0.0086 (13)
C2300.086 (5)0.070 (5)0.072 (6)0.019 (5)0.025 (4)0.022 (5)
C2400.102 (6)0.077 (5)0.090 (6)0.010 (5)0.024 (5)0.024 (5)
C2500.100 (8)0.068 (7)0.093 (8)0.022 (6)0.025 (7)0.015 (7)
C2600.087 (7)0.045 (5)0.064 (6)0.013 (5)0.021 (5)0.010 (5)
C2310.069 (3)0.056 (2)0.042 (2)0.013 (2)0.0024 (19)0.0069 (17)
C2410.097 (3)0.046 (2)0.061 (2)0.007 (2)0.015 (2)0.0059 (19)
C2510.102 (4)0.079 (4)0.097 (4)0.006 (4)0.012 (4)0.004 (4)
C2610.114 (5)0.064 (3)0.103 (4)0.033 (3)0.009 (3)0.001 (3)
C310.0462 (13)0.0504 (14)0.0720 (16)0.0306 (12)0.0042 (12)0.0067 (13)
C320.0490 (14)0.0583 (16)0.0680 (16)0.0294 (13)0.0030 (12)0.0089 (14)
C330.067 (2)0.0470 (15)0.103 (2)0.0304 (14)0.0268 (18)0.0005 (16)
C3400.096 (6)0.061 (5)0.112 (5)0.028 (5)0.042 (6)0.001 (5)
C3500.096 (8)0.073 (8)0.117 (9)0.027 (7)0.043 (8)0.011 (8)
C3600.104 (8)0.060 (7)0.112 (8)0.034 (6)0.064 (7)0.007 (6)
C3410.074 (3)0.093 (3)0.101 (3)0.044 (3)0.020 (3)0.021 (3)
C3510.065 (3)0.092 (5)0.127 (5)0.033 (3)0.030 (3)0.027 (4)
C3610.110 (5)0.104 (4)0.109 (4)0.054 (4)0.030 (4)0.008 (4)
C410.0435 (13)0.0795 (19)0.0525 (14)0.0333 (13)0.0020 (11)0.0166 (14)
C4210.045 (3)0.056 (3)0.044 (3)0.022 (3)0.007 (2)0.007 (3)
C4310.054 (3)0.058 (3)0.039 (3)0.025 (3)0.014 (2)0.003 (2)
C4410.059 (3)0.063 (3)0.032 (2)0.037 (2)0.006 (2)0.005 (2)
C4510.085 (4)0.079 (5)0.038 (3)0.042 (4)0.008 (3)0.013 (3)
C4610.056 (3)0.070 (4)0.035 (3)0.030 (3)0.008 (3)0.004 (3)
C4200.040 (3)0.103 (4)0.040 (2)0.040 (3)0.003 (2)0.004 (3)
C4300.070 (4)0.121 (5)0.041 (3)0.045 (4)0.006 (3)0.002 (3)
C4400.092 (4)0.115 (5)0.059 (3)0.060 (3)0.011 (3)0.019 (3)
C4500.108 (5)0.138 (7)0.074 (4)0.071 (5)0.008 (4)0.035 (5)
C4600.083 (4)0.112 (6)0.066 (4)0.048 (4)0.011 (4)0.022 (4)
Geometric parameters (Å, º) top
N1—C111.524 (4)C33—C3401.523 (7)
N1—C211.526 (3)C33—H3310.978
N1—C311.518 (3)C33—H3320.979
N1—C411.517 (3)C33—C3411.500 (5)
C11—C121.513 (4)C33—H3331.022
C11—H1110.975C33—H3340.977
C11—H1120.958C340—C3501.520 (7)
C12—C131.519 (4)C340—C3601.528 (7)
C12—H1210.993C340—H34010.993
C12—H1220.983C350—H35011.060
C13—C141.517 (5)C350—H35021.056
C13—H1310.980C350—H35031.052
C13—H1320.956C360—H36011.138
C14—C151.522 (6)C360—H36021.122
C14—C161.493 (5)C360—H36031.131
C14—H1410.972C341—C3511.524 (5)
C15—H1510.984C341—C3611.479 (6)
C15—H1520.984C341—H34111.032
C15—H1530.967C351—H35110.966
C16—H1610.974C351—H35120.964
C16—H1620.963C351—H35130.963
C16—H1630.971C361—H36110.977
C21—C221.517 (3)C361—H36120.960
C21—H2110.963C361—H36130.974
C21—H2120.977C41—C4211.420 (5)
C22—C2301.542 (7)C41—H4110.972
C22—H2210.979C41—H4120.976
C22—H2220.965C41—C4201.603 (5)
C22—C2311.503 (4)C41—H4130.975
C22—H2230.989C41—H4140.975
C22—H2240.946C421—C4311.518 (5)
C230—C2401.543 (7)C421—H42110.963
C230—H23010.959C421—H42120.983
C230—H23020.970C431—C4411.485 (5)
C240—C2501.521 (7)C431—H43110.981
C240—C2601.533 (7)C431—H43120.968
C240—H24010.994C441—C4511.508 (5)
C250—H25010.969C441—C4611.509 (6)
C250—H25020.965C441—H44110.965
C250—H25030.970C451—H45110.974
C260—H26010.950C451—H45120.965
C260—H26020.954C451—H45130.957
C260—H26030.947C461—H46110.967
C231—C2411.530 (4)C461—H46120.962
C231—H23110.949C461—H46130.973
C231—H23120.946C420—C4301.520 (5)
C241—C2511.501 (6)C420—H42010.961
C241—C2611.561 (6)C420—H42020.975
C241—H24110.991C430—C4401.522 (6)
C251—H25110.974C430—H43010.966
C251—H25120.988C430—H43020.978
C251—H25130.973C440—C4501.531 (6)
C261—H26110.977C440—C4601.521 (6)
C261—H26120.958C440—H44010.994
C261—H26130.975C450—H45010.955
C31—C321.505 (3)C450—H45020.972
C31—H3110.976C450—H45030.966
C31—H3120.975C460—H46010.949
C32—C331.524 (3)C460—H46020.959
C32—H3210.968C460—H46030.960
C32—H3220.976
C11—N1—C21105.94 (16)C32—C33—C340116.05 (7)
C11—N1—C31110.7 (2)C32—C33—H331109.2
C21—N1—C31111.9 (2)C340—C33—H331109.0
C11—N1—C41109.5 (2)C32—C33—H332107.6
C21—N1—C41112.56 (19)C340—C33—H332106.1
C31—N1—C41106.37 (12)H331—C33—H332108.8
N1—C11—C12115.6 (2)C32—C33—C341116.02 (7)
N1—C11—H111109.1C32—C33—H333107.9
C12—C11—H111109.5C341—C33—H333107.6
N1—C11—H112107.1C32—C33—H334109.7
C12—C11—H112109.5C341—C33—H334107.4
H111—C11—H112105.6H333—C33—H334108.0
C11—C12—C13110.3 (3)C33—C340—C350112.92 (7)
C11—C12—H121107.7C33—C340—C360112.93 (7)
C13—C12—H121111.6C350—C340—C360111.31 (7)
C11—C12—H122109.2C33—C340—H3401108.3
C13—C12—H122111.0C350—C340—H3401105.6
H121—C12—H122106.9C360—C340—H3401105.1
C12—C13—C14114.9 (3)C340—C350—H3501108.0
C12—C13—H131105.8C340—C350—H3502105.9
C14—C13—H131104.9H3501—C350—H3502111.1
C12—C13—H132111.0C340—C350—H3503108.3
C14—C13—H132112.4H3501—C350—H3503111.5
H131—C13—H132107.3H3502—C350—H3503111.8
C13—C14—C15110.9 (4)C340—C360—H3601107.0
C13—C14—C16113.5 (4)C340—C360—H3602104.3
C15—C14—C16111.1 (4)H3601—C360—H3602112.2
C13—C14—H141107.1C340—C360—H3603106.4
C15—C14—H141108.4H3601—C360—H3603112.9
C16—C14—H141105.4H3602—C360—H3603113.2
C14—C15—H151110.7C33—C341—C351112.93 (7)
C14—C15—H152107.1C33—C341—C361112.95 (7)
H151—C15—H152108.1C351—C341—C361111.33 (7)
C14—C15—H153110.1C33—C341—H3411106.6
H151—C15—H153111.1C351—C341—H3411108.7
H152—C15—H153109.7C361—C341—H3411103.7
C14—C16—H161107.6C341—C351—H3511109.2
C14—C16—H162108.1C341—C351—H3512113.1
H161—C16—H162110.2H3511—C351—H3512107.9
C14—C16—H163109.2C341—C351—H3513111.1
H161—C16—H163110.3H3511—C351—H3513106.7
H162—C16—H163111.4H3512—C351—H3513108.6
N1—C21—C22115.67 (5)C341—C361—H3611109.1
N1—C21—H211105.7C341—C361—H3612109.7
C22—C21—H211108.8H3611—C361—H3612110.7
N1—C21—H212108.4C341—C361—H3613108.7
C22—C21—H212109.4H3611—C361—H3613107.7
H211—C21—H212108.6H3612—C361—H3613110.9
C21—C22—C230110.40 (7)N1—C41—C421116.00 (7)
C21—C22—H221108.9N1—C41—H411108.3
C230—C22—H221109.8C421—C41—H411111.2
C21—C22—H222110.1N1—C41—H412107.0
C230—C22—H222108.7C421—C41—H412105.1
H221—C22—H222108.9H411—C41—H412109.0
C21—C22—C231110.42 (7)N1—C41—C420115.39 (7)
C21—C22—H223109.2N1—C41—H413106.3
C231—C22—H223110.4C420—C41—H413109.0
C21—C22—H224110.8N1—C41—H414109.1
C231—C22—H224108.9C420—C41—H414109.2
H223—C22—H224107.0H413—C41—H414107.6
C22—C230—C240116.16 (7)C41—C421—C431110.12 (7)
C22—C230—H2301108.3C41—C421—H4211107.9
C240—C230—H2301106.5C431—C421—H4211107.5
C22—C230—H2302108.8C41—C421—H4212110.8
C240—C230—H2302107.0C431—C421—H4212112.1
H2301—C230—H2302110.0H4211—C421—H4212108.2
C230—C240—C250112.89 (7)C421—C431—C441116.17 (7)
C230—C240—C260112.99 (7)C421—C431—H4311107.6
C250—C240—C260111.29 (7)C441—C431—H4311106.4
C230—C240—H2401105.7C421—C431—H4312107.6
C250—C240—H2401110.0C441—C431—H4312109.6
C260—C240—H2401103.4H4311—C431—H4312109.3
C240—C250—H2501110.4C431—C441—C451112.80 (7)
C240—C250—H2502106.3C431—C441—C461112.82 (7)
H2501—C250—H2502109.0C451—C441—C461111.28 (7)
C240—C250—H2503111.2C431—C441—H4411107.3
H2501—C250—H2503110.0C451—C441—H4411106.5
H2502—C250—H2503109.7C461—C441—H4411105.6
C240—C260—H2601110.1C441—C451—H4511109.1
C240—C260—H2602111.2C441—C451—H4512108.9
H2601—C260—H2602109.4H4511—C451—H4512109.8
C240—C260—H2603108.1C441—C451—H4513110.6
H2601—C260—H2603108.6H4511—C451—H4513109.1
H2602—C260—H2603109.4H4512—C451—H4513109.4
C22—C231—C241115.95 (7)C441—C461—H4611110.1
C22—C231—H2311108.6C441—C461—H4612108.6
C241—C231—H2311111.8H4611—C461—H4612110.1
C22—C231—H2312107.0C441—C461—H4613109.0
C241—C231—H2312104.4H4611—C461—H4613109.9
H2311—C231—H2312108.6H4612—C461—H4613109.1
C231—C241—C251112.90 (7)C41—C420—C430110.55 (7)
C231—C241—C261112.90 (7)C41—C420—H4201107.3
C251—C241—C261111.32 (7)C430—C420—H4201109.0
C231—C241—H2411107.4C41—C420—H4202110.9
C251—C241—H2411104.6C430—C420—H4202110.3
C261—C241—H2411107.1H4201—C420—H4202108.6
C241—C251—H2511109.0C420—C430—C440116.13 (7)
C241—C251—H2512108.3C420—C430—H4301106.6
H2511—C251—H2512108.1C440—C430—H4301106.4
C241—C251—H2513109.4C420—C430—H4302109.6
H2511—C251—H2513109.7C440—C430—H4302109.6
H2512—C251—H2513112.2H4301—C430—H4302108.2
C241—C261—H2611110.3C430—C440—C450112.86 (7)
C241—C261—H2612111.6C430—C440—C460112.94 (7)
H2611—C261—H2612109.0C450—C440—C460111.26 (7)
C241—C261—H2613110.0C430—C440—H4401105.0
H2611—C261—H2613108.3C450—C440—H4401108.4
H2612—C261—H2613107.6C460—C440—H4401105.8
N1—C31—C32115.58 (5)C440—C450—H4501110.6
N1—C31—H311106.5C440—C450—H4502110.4
C32—C31—H311110.2H4501—C450—H4502108.2
N1—C31—H312105.6C440—C450—H4503110.6
C32—C31—H312109.8H4501—C450—H4503109.4
H311—C31—H312109.0H4502—C450—H4503107.7
C31—C32—C33110.43 (5)C440—C460—H4601107.9
C31—C32—H321109.0C440—C460—H4602110.4
C33—C32—H321108.0H4601—C460—H4602109.5
C31—C32—H322110.4C440—C460—H4603110.4
C33—C32—H322110.1H4601—C460—H4603108.5
H321—C32—H322108.8H4602—C460—H4603110.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C230—H2302···C2610.971.572.360 (10)136
C250—H2502···C250i0.972.082.841 (10)135
C260—H2601···C260ii0.951.792.545 (10)134
Symmetry codes: (i) y, x, z+1; (ii) xy, y, z+4/3.
(I_250K) tetrakis(4-methylpentyl)azanium bromide top
Crystal data top
C24H52N+·BrDx = 0.985 Mg m3
Mr = 434.59Cu Kα radiation, λ = 1.54184 Å
Trigonal, P3221Cell parameters from 18120 reflections
Hall symbol: P 32 2"θ = 3–77°
a = 15.4995 (2) ŵ = 1.93 mm1
c = 21.1346 (3) ÅT = 250 K
V = 4397.06 (12) Å3Plate, colourless
Z = 60.15 × 0.14 × 0.07 mm
F(000) = 1428
Data collection top
Oxford SuperNova Dual
diffractometer with Cu at zero and Atlas detector
4391 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 76.9°, θmin = 3.3°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
h = 1919
Tmin = 0.60, Tmax = 0.87k = 1919
94951 measured reflectionsl = 2626
6128 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049 Method = Modified Sheldrick w = 1/[σ2(F2) + (0.12P)2 + 0.13P],
where P = [max(Fo2,0) + 2Fc2]/3
wR(F2) = 0.178(Δ/σ)max = 0.004
S = 0.96Δρmax = 0.21 e Å3
6128 reflectionsΔρmin = 0.24 e Å3
366 parametersAbsolute structure: Flack (1983), with 2710 Friedel pairs
864 restraintsAbsolute structure parameter: 0.03 (3)
Primary atom site location: structure-invariant direct methods
Crystal data top
C24H52N+·BrZ = 6
Mr = 434.59Cu Kα radiation
Trigonal, P3221µ = 1.93 mm1
a = 15.4995 (2) ÅT = 250 K
c = 21.1346 (3) Å0.15 × 0.14 × 0.07 mm
V = 4397.06 (12) Å3
Data collection top
Oxford SuperNova Dual
diffractometer with Cu at zero and Atlas detector
6128 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
4391 reflections with I > 2σ(I)
Tmin = 0.60, Tmax = 0.87Rint = 0.037
94951 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.178Δρmax = 0.21 e Å3
S = 0.96Δρmin = 0.24 e Å3
6128 reflectionsAbsolute structure: Flack (1983), with 2710 Friedel pairs
366 parametersAbsolute structure parameter: 0.03 (3)
864 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br10.85154 (4)0.51981 (5)0.71443 (2)0.1359
N10.58832 (17)0.43385 (19)0.59685 (11)0.1058
C110.6112 (2)0.5404 (2)0.58831 (18)0.1124
C120.7076 (3)0.6194 (2)0.6178 (2)0.1353
C130.7278 (4)0.7217 (3)0.5993 (3)0.1600
C1400.8029 (7)0.8080 (5)0.6372 (4)0.19240.382 (14)
C1500.8116 (16)0.9046 (7)0.6191 (10)0.20760.382 (14)
C1600.9014 (10)0.8133 (12)0.6416 (12)0.19780.382 (14)
C1410.8325 (5)0.8076 (4)0.6082 (3)0.18980.618 (14)
C1510.8489 (8)0.9039 (6)0.5809 (7)0.20330.618 (14)
C1610.8700 (10)0.8184 (8)0.6740 (6)0.22340.618 (14)
C210.4895 (2)0.3702 (2)0.56421 (18)0.1131
C220.4489 (3)0.2587 (3)0.5675 (2)0.1369
C230.3425 (3)0.2035 (3)0.5452 (3)0.1556
C2400.2666 (5)0.1273 (11)0.5886 (5)0.19840.248 (8)
C2500.1624 (7)0.088 (2)0.5672 (11)0.21190.248 (8)
C2600.2878 (15)0.0474 (14)0.6066 (14)0.20260.248 (8)
C2410.2913 (4)0.0922 (4)0.5430 (3)0.18830.752 (8)
C2510.1839 (5)0.0438 (5)0.5245 (6)0.22150.752 (8)
C2610.3467 (6)0.0533 (5)0.5068 (6)0.21530.752 (8)
C310.6710 (3)0.4197 (3)0.56948 (14)0.1125
C320.6976 (3)0.4511 (4)0.50075 (15)0.1282
C330.7777 (3)0.4306 (4)0.47896 (17)0.1460
C3400.7969 (5)0.4342 (7)0.4095 (3)0.19150.466 (18)
C3500.8944 (10)0.4438 (17)0.3935 (4)0.20350.466 (18)
C3600.7780 (16)0.5065 (15)0.3747 (5)0.20270.466 (18)
C3410.8079 (5)0.4499 (6)0.4113 (3)0.17210.534 (18)
C3510.8729 (10)0.4103 (11)0.3913 (4)0.18070.534 (18)
C3610.8466 (14)0.5541 (10)0.3918 (6)0.19030.534 (18)
C410.5848 (2)0.4104 (4)0.66678 (14)0.1222
C4210.4977 (7)0.4011 (9)0.7020 (2)0.12790.545 (12)
C4310.4890 (6)0.3529 (6)0.7654 (3)0.13390.545 (12)
C4410.4225 (6)0.3577 (5)0.8116 (2)0.14590.545 (12)
C4510.4296 (9)0.3212 (10)0.8757 (3)0.17400.545 (12)
C4610.3189 (7)0.3143 (11)0.7894 (5)0.17070.545 (12)
C4200.5238 (8)0.4444 (9)0.7091 (3)0.13820.455 (12)
C4300.5085 (6)0.3992 (8)0.7751 (3)0.16930.455 (12)
C4400.4167 (8)0.3005 (7)0.7864 (4)0.18710.455 (12)
C4500.4077 (11)0.2626 (12)0.8528 (7)0.19470.455 (12)
C4600.3236 (8)0.2956 (13)0.7635 (7)0.18970.455 (12)
H1110.55420.54240.60720.1331*
H1120.60960.55010.54240.1313*
H1210.70360.61240.66320.1605*
H1220.76090.60910.60170.1613*
H1310.66490.72030.59960.1879*0.382 (14)
H1320.75460.73370.55690.1880*0.382 (14)
H14010.77840.79390.68120.2248*0.382 (14)
H15010.84480.95380.65450.3120*0.382 (14)
H15020.74240.89150.61250.3122*0.382 (14)
H15030.85100.92970.57920.3121*0.382 (14)
H16010.94590.86420.67100.2899*0.382 (14)
H16020.89590.74970.65300.2897*0.382 (14)
H16030.92760.83240.59880.2901*0.382 (14)
H1330.68870.73710.62760.1880*0.618 (14)
H1340.70550.71850.55670.1881*0.618 (14)
H14110.87470.78960.58400.2223*0.618 (14)
H15110.92020.95190.57930.3010*0.618 (14)
H15120.81600.93010.60640.3014*0.618 (14)
H15130.82140.89240.53820.3008*0.618 (14)
H16110.92430.88580.68010.3262*0.618 (14)
H16120.81290.80480.70090.3259*0.618 (14)
H16130.89220.77130.68160.3258*0.618 (14)
H2110.44220.38600.58210.1333*
H2120.50110.39150.52000.1349*
H2210.45470.24410.61230.1624*
H2220.48700.23870.54110.1625*
H2310.32480.25360.53470.1830*0.248 (8)
H2320.33830.16490.50820.1832*0.248 (8)
H24010.27510.16480.62790.2330*0.248 (8)
H25010.11760.02810.59150.3141*0.248 (8)
H25020.14450.13940.57340.3140*0.248 (8)
H25030.15930.07170.52200.3140*0.248 (8)
H26010.22600.01520.60220.2941*0.248 (8)
H26020.31250.05510.65000.2942*0.248 (8)
H26030.33650.04690.57710.2939*0.248 (8)
H2330.30640.22790.57010.1831*0.752 (8)
H2340.34480.22230.50180.1832*0.752 (8)
H24110.28910.07010.58700.2282*0.752 (8)
H25110.16410.02390.50450.3411*0.752 (8)
H25120.13840.03470.56180.3414*0.752 (8)
H25130.18010.08990.49110.3407*0.752 (8)
H26110.31750.01790.51520.3261*0.752 (8)
H26120.41610.09000.52070.3262*0.752 (8)
H26130.34220.06360.46190.3259*0.752 (8)
H3110.73070.46160.59460.1344*
H3120.65230.34930.57540.1333*
H3210.72330.52190.49600.1531*
H3220.63970.41720.47390.1533*
H3310.83950.48140.49840.1764*0.466 (18)
H3320.76360.36640.49550.1764*0.466 (18)
H34010.74480.36890.39250.2312*0.466 (18)
H35010.89530.42410.35020.3081*0.466 (18)
H35020.94510.51180.40030.3080*0.466 (18)
H35030.90550.40210.42250.3079*0.466 (18)
H36010.79550.50920.33030.3048*0.466 (18)
H36020.82130.57020.39500.3050*0.466 (18)
H36030.70800.48880.37810.3049*0.466 (18)
H3330.83660.47190.50480.1763*0.534 (18)
H3340.75640.36150.48770.1766*0.534 (18)
H34110.74580.41420.38590.2023*0.534 (18)
H35110.90560.44040.35180.2661*0.534 (18)
H35120.92140.42690.42520.2658*0.534 (18)
H35130.83350.33870.38630.2660*0.534 (18)
H36110.87360.56420.34990.2799*0.534 (18)
H36120.89820.59300.42210.2800*0.534 (18)
H36130.79570.57270.39250.2799*0.534 (18)
H4110.64680.46140.68570.1437*0.477 (12)
H4120.58010.34620.67020.1442*0.477 (12)
H42110.50810.46710.71080.1508*0.545 (12)
H42120.43660.36280.67790.1507*0.545 (12)
H43110.55410.38210.78480.1585*0.545 (12)
H43120.46500.28290.75730.1583*0.545 (12)
H44110.44590.42810.81640.1728*0.545 (12)
H45110.40880.35180.90980.2608*0.545 (12)
H45120.50090.34100.88180.2608*0.545 (12)
H45130.38650.24660.87600.2609*0.545 (12)
H46110.27670.32760.82280.2550*0.545 (12)
H46120.29540.23780.78540.2546*0.545 (12)
H46130.31970.34620.74470.2550*0.545 (12)
H4130.65340.44380.68250.1434*0.523 (12)
H4140.55460.33930.67100.1441*0.523 (12)
H42010.56230.51600.71420.1651*0.455 (12)
H42020.45960.42680.69030.1648*0.455 (12)
H43010.50230.44350.80470.1978*0.455 (12)
H43020.56600.39320.78650.1983*0.455 (12)
H44010.42280.25340.75800.2233*0.455 (12)
H45010.36750.19090.85330.2928*0.455 (12)
H45020.37550.28990.87840.2930*0.455 (12)
H45030.47280.28220.87000.2929*0.455 (12)
H46010.26550.23640.77860.2879*0.455 (12)
H46020.32650.35510.78120.2881*0.455 (12)
H46030.32180.29760.71800.2882*0.455 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1074 (3)0.1872 (5)0.1140 (3)0.0744 (3)0.00544 (19)0.0263 (3)
N10.1075 (14)0.1332 (17)0.0954 (13)0.0743 (13)0.0073 (11)0.0078 (13)
C110.126 (2)0.128 (2)0.1037 (18)0.0787 (18)0.0133 (16)0.0008 (16)
C120.148 (3)0.136 (2)0.131 (2)0.078 (2)0.032 (2)0.011 (2)
C130.182 (3)0.137 (3)0.163 (3)0.082 (3)0.040 (3)0.015 (2)
C1400.205 (7)0.155 (5)0.193 (7)0.072 (6)0.046 (6)0.033 (5)
C1500.220 (9)0.159 (7)0.213 (10)0.071 (8)0.048 (9)0.032 (8)
C1600.203 (8)0.166 (8)0.197 (9)0.072 (7)0.036 (8)0.042 (7)
C1410.213 (6)0.146 (4)0.184 (6)0.070 (4)0.041 (5)0.009 (4)
C1510.228 (8)0.147 (5)0.194 (8)0.063 (6)0.029 (7)0.002 (5)
C1610.238 (8)0.174 (7)0.193 (7)0.053 (7)0.057 (7)0.008 (6)
C210.1073 (19)0.137 (2)0.1053 (18)0.0691 (18)0.0092 (15)0.0082 (16)
C220.126 (2)0.140 (2)0.145 (3)0.067 (2)0.013 (2)0.011 (2)
C230.132 (3)0.150 (3)0.167 (3)0.057 (2)0.015 (3)0.002 (3)
C2400.165 (7)0.170 (7)0.194 (7)0.035 (6)0.007 (6)0.002 (6)
C2500.168 (9)0.181 (10)0.204 (10)0.026 (9)0.005 (9)0.008 (9)
C2600.176 (9)0.163 (9)0.195 (10)0.029 (8)0.005 (9)0.010 (9)
C2410.157 (4)0.151 (4)0.223 (6)0.051 (3)0.016 (4)0.003 (4)
C2510.163 (5)0.180 (6)0.262 (8)0.041 (5)0.009 (6)0.018 (6)
C2610.188 (6)0.162 (6)0.270 (8)0.068 (5)0.016 (6)0.010 (5)
C310.1097 (18)0.130 (2)0.1150 (18)0.0729 (18)0.0025 (15)0.0010 (18)
C320.121 (2)0.148 (3)0.118 (2)0.069 (2)0.0064 (18)0.010 (2)
C330.133 (3)0.152 (3)0.155 (3)0.072 (2)0.021 (2)0.009 (2)
C3400.176 (6)0.192 (6)0.175 (5)0.068 (6)0.050 (5)0.015 (5)
C3500.183 (7)0.200 (8)0.194 (8)0.070 (7)0.064 (7)0.017 (7)
C3600.194 (8)0.195 (8)0.173 (7)0.062 (7)0.062 (7)0.005 (6)
C3410.146 (5)0.188 (5)0.180 (5)0.081 (4)0.041 (4)0.020 (5)
C3510.149 (6)0.179 (7)0.205 (7)0.075 (5)0.054 (6)0.024 (6)
C3610.166 (8)0.203 (7)0.187 (7)0.080 (6)0.028 (6)0.007 (6)
C410.118 (2)0.160 (3)0.0991 (17)0.078 (2)0.0048 (16)0.0232 (18)
C4210.137 (4)0.167 (5)0.096 (3)0.088 (4)0.002 (3)0.016 (3)
C4310.158 (5)0.165 (6)0.097 (3)0.095 (4)0.006 (3)0.015 (3)
C4410.190 (5)0.181 (6)0.090 (3)0.110 (5)0.009 (3)0.015 (4)
C4510.222 (8)0.202 (8)0.104 (5)0.111 (6)0.001 (5)0.026 (5)
C4610.190 (6)0.205 (8)0.110 (5)0.093 (6)0.032 (5)0.019 (5)
C4200.123 (5)0.184 (6)0.111 (4)0.080 (4)0.004 (4)0.013 (4)
C4300.155 (6)0.210 (7)0.121 (5)0.074 (5)0.007 (5)0.012 (5)
C4400.185 (6)0.211 (8)0.135 (6)0.077 (6)0.011 (5)0.012 (6)
C4500.204 (9)0.211 (10)0.141 (7)0.083 (8)0.003 (7)0.014 (7)
C4600.180 (8)0.219 (10)0.134 (7)0.073 (7)0.026 (6)0.005 (7)
Geometric parameters (Å, º) top
N1—C111.517 (3)C31—H3110.978
N1—C211.511 (3)C31—H3120.987
N1—C311.519 (3)C32—C331.499 (4)
N1—C411.516 (3)C32—H3210.966
C11—C121.513 (4)C32—H3220.966
C11—H1110.984C33—C3401.493 (6)
C11—H1120.985C33—H3310.976
C12—C131.506 (4)C33—H3320.971
C12—H1210.964C33—C3411.488 (6)
C12—H1220.977C33—H3330.978
C13—C1401.492 (6)C33—H3340.968
C13—H1310.964C340—C3501.483 (7)
C13—H1320.966C340—C3601.488 (7)
C13—C1411.510 (6)C340—H34010.994
C13—H1330.962C350—H35010.965
C13—H1340.958C350—H35020.960
C140—C1501.485 (7)C350—H35030.966
C140—C1601.489 (7)C360—H36010.972
C140—H14010.989C360—H36020.974
C150—H15011.007C360—H36030.979
C150—H15020.996C341—C3511.479 (6)
C150—H15030.999C341—C3611.473 (7)
C160—H16010.970C341—H34110.993
C160—H16020.976C351—H35110.967
C160—H16030.975C351—H35120.976
C141—C1511.497 (6)C351—H35130.967
C141—C1611.485 (7)C361—H36110.959
C141—H14110.975C361—H36120.966
C151—H15110.977C361—H36130.966
C151—H15120.961C41—C4211.485 (5)
C151—H15130.975C41—H4110.974
C161—H16110.968C41—H4120.963
C161—H16120.982C41—C4201.572 (6)
C161—H16130.963C41—H4130.978
C21—C221.517 (4)C41—H4140.962
C21—H2110.960C421—C4311.507 (5)
C21—H2120.976C421—H42110.970
C22—C231.503 (4)C421—H42120.972
C22—H2210.988C431—C4411.449 (6)
C22—H2220.969C431—H43110.967
C23—C2401.494 (7)C431—H43120.970
C23—H2310.970C441—C4511.493 (6)
C23—H2320.967C441—C4611.473 (7)
C23—C2411.497 (6)C441—H44110.967
C23—H2330.971C451—H45111.001
C23—H2340.957C451—H45120.996
C240—C2501.483 (7)C451—H45131.005
C240—C2601.481 (7)C461—H46111.050
C240—H24010.985C461—H46121.056
C250—H25010.982C461—H46131.064
C250—H25020.975C420—C4301.525 (6)
C250—H25030.984C420—H42010.969
C260—H26010.968C420—H42020.976
C260—H26020.978C430—C4401.499 (7)
C260—H26030.980C430—H43010.968
C241—C2511.496 (6)C430—H43020.971
C241—C2611.486 (7)C440—C4501.501 (7)
C241—H24110.984C440—C4601.487 (7)
C251—H25111.026C440—H44010.986
C251—H25121.019C450—H45010.964
C251—H25131.026C450—H45020.966
C261—H26110.977C450—H45030.967
C261—H26120.977C460—H46010.964
C261—H26130.971C460—H46020.976
C31—C321.522 (4)C460—H46030.964
C11—N1—C21105.39 (13)N1—C31—H312108.0
C11—N1—C31110.9 (2)C32—C31—H312111.0
C21—N1—C31112.6 (3)H311—C31—H312108.8
C11—N1—C41109.8 (3)C31—C32—C33110.25 (5)
C21—N1—C41112.7 (2)C31—C32—H321110.8
C31—N1—C41105.54 (13)C33—C32—H321107.0
N1—C11—C12115.51 (5)C31—C32—H322110.9
N1—C11—H111105.2C33—C32—H322110.3
C12—C11—H111110.3H321—C32—H322107.4
N1—C11—H112105.9C32—C33—C340117.70 (7)
C12—C11—H112111.9C32—C33—H331106.4
H111—C11—H112107.6C340—C33—H331106.8
C11—C12—C13110.30 (5)C32—C33—H332108.7
C11—C12—H121109.7C340—C33—H332109.3
C13—C12—H121110.1H331—C33—H332107.6
C11—C12—H122107.4C32—C33—C341117.62 (7)
C13—C12—H122109.5C32—C33—H333106.9
H121—C12—H122109.8C341—C33—H333108.0
C12—C13—C140117.62 (7)C32—C33—H334108.4
C12—C13—H131107.4C341—C33—H334107.7
C140—C13—H131110.1H333—C33—H334107.9
C12—C13—H132106.6C33—C340—C350113.73 (7)
C140—C13—H132104.9C33—C340—C360113.80 (7)
H131—C13—H132110.0C350—C340—C360112.74 (7)
C12—C13—C141117.59 (7)C33—C340—H3401105.8
C12—C13—H133106.0C350—C340—H3401106.8
C141—C13—H133103.7C360—C340—H3401102.8
C12—C13—H134108.0C340—C350—H3501111.0
C141—C13—H134111.2C340—C350—H3502108.0
H133—C13—H134110.0H3501—C350—H3502110.9
C13—C140—C150113.76 (7)C340—C350—H3503107.5
C13—C140—C160113.74 (7)H3501—C350—H3503110.8
C150—C140—C160112.73 (7)H3502—C350—H3503108.5
C13—C140—H1401105.4C340—C360—H3601110.8
C150—C140—H1401107.2C340—C360—H3602104.5
C160—C140—H1401102.9H3601—C360—H3602110.2
C140—C150—H1501109.1C340—C360—H3603111.1
C140—C150—H1502106.6H3601—C360—H3603109.3
H1501—C150—H1502110.4H3602—C360—H3603110.9
C140—C150—H1503109.8C33—C341—C351113.75 (7)
H1501—C150—H1503110.5C33—C341—C361113.78 (7)
H1502—C150—H1503110.4C351—C341—C361112.76 (7)
C140—C160—H1601112.2C33—C341—H3411106.7
C140—C160—H1602112.9C351—C341—H3411106.7
H1601—C160—H1602109.2C361—C341—H3411102.0
C140—C160—H1603102.6C341—C351—H3511110.4
H1601—C160—H1603109.3C341—C351—H3512106.0
H1602—C160—H1603110.5H3511—C351—H3512111.0
C13—C141—C151113.81 (7)C341—C351—H3513109.6
C13—C141—C161113.73 (7)H3511—C351—H3513109.7
C151—C141—C161112.76 (7)H3512—C351—H3513110.1
C13—C141—H1411105.2C341—C361—H3611110.1
C151—C141—H1411106.3C341—C361—H3612104.7
C161—C141—H1411104.0H3611—C361—H3612110.7
C141—C151—H1511109.7C341—C361—H3613112.2
C141—C151—H1512110.1H3611—C361—H3613108.7
H1511—C151—H1512109.6H3612—C361—H3613110.4
C141—C151—H1513109.4N1—C41—C421115.66 (7)
H1511—C151—H1513109.4N1—C41—H411107.7
H1512—C151—H1513108.7C421—C41—H411110.6
C141—C161—H1611109.1N1—C41—H412107.2
C141—C161—H1612104.9C421—C41—H412105.5
H1611—C161—H1612111.0H411—C41—H412110.1
C141—C161—H1613109.8N1—C41—C420115.44 (7)
H1611—C161—H1613110.4N1—C41—H413107.8
H1612—C161—H1613111.5C420—C41—H413107.7
N1—C21—C22115.54 (5)N1—C41—H414107.6
N1—C21—H211108.0C420—C41—H414107.6
C22—C21—H211109.7H413—C41—H414110.7
N1—C21—H212105.1C41—C421—C431110.18 (7)
C22—C21—H212109.2C41—C421—H4211109.3
H211—C21—H212109.0C431—C421—H4211106.1
C21—C22—C23110.26 (5)C41—C421—H4212110.9
C21—C22—H221105.7C431—C421—H4212110.2
C23—C22—H221111.7H4211—C421—H4212110.1
C21—C22—H222111.4C421—C431—C441117.63 (7)
C23—C22—H222108.0C421—C431—H4311109.4
H221—C22—H222109.8C441—C431—H4311107.1
C22—C23—C240117.63 (7)C421—C431—H4312106.7
C22—C23—H231106.6C441—C431—H4312107.0
C240—C23—H231110.3H4311—C431—H4312108.9
C22—C23—H232108.7C431—C441—C451113.72 (7)
C240—C23—H232102.9C431—C441—C461113.71 (7)
H231—C23—H232110.6C451—C441—C461112.74 (7)
C22—C23—C241117.66 (7)C431—C441—H4411104.7
C22—C23—H233106.9C451—C441—H4411106.0
C241—C23—H233112.9C461—C441—H4411104.9
C22—C23—H234105.3C441—C451—H4511111.7
C241—C23—H234103.8C441—C451—H4512106.4
H233—C23—H234109.9H4511—C451—H4512109.3
C23—C240—C250113.76 (7)C441—C451—H4513108.0
C23—C240—C260113.76 (7)H4511—C451—H4513110.7
C250—C240—C260112.75 (7)H4512—C451—H4513110.6
C23—C240—H2401103.3C441—C461—H4611109.8
C250—C240—H2401107.2C441—C461—H4612103.0
C260—C240—H2401104.9H4611—C461—H4612112.0
C240—C250—H2501109.8C441—C461—H4613108.3
C240—C250—H2502108.7H4611—C461—H4613111.6
H2501—C250—H2502110.3H4612—C461—H4613111.6
C240—C250—H2503107.8C41—C420—C430110.36 (7)
H2501—C250—H2503110.2C41—C420—H4201108.6
H2502—C250—H2503110.1C430—C420—H4201106.9
C240—C260—H2601106.9C41—C420—H4202112.0
C240—C260—H2602112.1C430—C420—H4202109.9
H2601—C260—H2602110.0H4201—C420—H4202108.9
C240—C260—H2603109.7C420—C430—C440117.67 (7)
H2601—C260—H2603108.2C420—C430—H4301108.2
H2602—C260—H2603109.9C440—C430—H4301103.9
C23—C241—C251113.73 (7)C420—C430—H4302109.4
C23—C241—C261113.74 (7)C440—C430—H4302108.1
C251—C241—C261112.70 (7)H4301—C430—H4302109.2
C23—C241—H2411106.1C430—C440—C450113.77 (7)
C251—C241—H2411103.7C430—C440—C460113.79 (7)
C261—C241—H2411105.7C450—C440—C460112.75 (7)
C241—C251—H2511108.0C430—C440—H4401105.3
C241—C251—H2512112.7C450—C440—H4401107.6
H2511—C251—H2512110.2C460—C440—H4401102.4
C241—C251—H2513105.5C440—C450—H4501110.0
H2511—C251—H2513109.7C440—C450—H4502108.6
H2512—C251—H2513110.6H4501—C450—H4502108.7
C241—C261—H2611109.3C440—C450—H4503110.6
C241—C261—H2612107.4H4501—C450—H4503109.3
H2611—C261—H2612110.9H4502—C450—H4503109.7
C241—C261—H2613109.5C440—C460—H4601111.3
H2611—C261—H2613109.4C440—C460—H4602104.0
H2612—C261—H2613110.4H4601—C460—H4602110.6
N1—C31—C32115.52 (5)C440—C460—H4603111.5
N1—C31—H311106.5H4601—C460—H4603109.5
C32—C31—H311106.8H4602—C460—H4603109.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C150—H1501···C150i1.012.293.256 (15)161
C23—H232···C2610.971.802.497 (15)126
C250—H2502···C161ii0.982.603.367 (15)136
C260—H2602···C260iii0.982.152.841 (15)126
C260—H2603···C2610.981.492.281 (15)133
C251—H2513···C250iv1.032.533.475 (15)152
Symmetry codes: (i) xy+1, y+2, z+4/3; (ii) xy, y+1, z+4/3; (iii) xy, y, z+4/3; (iv) y, x, z+1.
(I_100KC) tetrakis(4-methylpentyl)azanium bromide top
Crystal data top
C24H52N+·BrDx = 1.043 Mg m3
Mr = 434.59Cu Kα radiation, λ = 1.54184 Å
Trigonal, P3221Cell parameters from 30678 reflections
Hall symbol: P 32 2"θ = 3–76°
a = 15.1327 (3) ŵ = 2.05 mm1
c = 20.9326 (4) ÅT = 100 K
V = 4151.30 (13) Å3Plate, colourless
Z = 60.15 × 0.14 × 0.07 mm
F(000) = 1428
Data collection top
Oxford SuperNova Dual
diffractometer with Cu at zero and Atlas detector
5336 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ω scansθmax = 76.6°, θmin = 3.4°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
h = 1818
Tmin = 0.59, Tmax = 0.87k = 1919
88138 measured reflectionsl = 2626
5768 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041 Method = Modified Sheldrick w = 1/[σ2(F2) + (0.09P)2 + 1.26P],
where P = [max(Fo2,0) + 2Fc2]/3
wR(F2) = 0.128(Δ/σ)max = 0.003
S = 0.98Δρmax = 0.42 e Å3
5768 reflectionsΔρmin = 0.44 e Å3
347 parametersAbsolute structure: Flack (1983), with 2546 Friedel pairs
648 restraintsAbsolute structure parameter: 0.01 (3)
Primary atom site location: structure-invariant direct methods
Crystal data top
C24H52N+·BrZ = 6
Mr = 434.59Cu Kα radiation
Trigonal, P3221µ = 2.05 mm1
a = 15.1327 (3) ÅT = 100 K
c = 20.9326 (4) Å0.15 × 0.14 × 0.07 mm
V = 4151.30 (13) Å3
Data collection top
Oxford SuperNova Dual
diffractometer with Cu at zero and Atlas detector
5768 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
5336 reflections with I > 2σ(I)
Tmin = 0.59, Tmax = 0.87Rint = 0.040
88138 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.128Δρmax = 0.42 e Å3
S = 0.98Δρmin = 0.44 e Å3
5768 reflectionsAbsolute structure: Flack (1983), with 2546 Friedel pairs
347 parametersAbsolute structure parameter: 0.01 (3)
648 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br10.84910 (3)0.52779 (3)0.717639 (16)0.0708
N10.58292 (18)0.42813 (19)0.59830 (11)0.0597
C110.6078 (2)0.5379 (2)0.58733 (15)0.0562
C120.7105 (3)0.6199 (3)0.61142 (17)0.0654
C130.7233 (3)0.7250 (3)0.60066 (18)0.0715
C140.8317 (4)0.8128 (3)0.6056 (2)0.0853
C150.8367 (5)0.9129 (4)0.5891 (3)0.1042
C160.8822 (4)0.8187 (4)0.6672 (3)0.1063
C210.4809 (2)0.3607 (2)0.56551 (14)0.0618
C220.4398 (2)0.2472 (2)0.57046 (18)0.0750
C2300.3394 (6)0.1880 (4)0.5326 (4)0.09870.272 (7)
C2400.2454 (6)0.1122 (7)0.5713 (6)0.11820.272 (7)
C2500.1500 (9)0.0558 (13)0.5307 (10)0.11410.272 (7)
C2600.2638 (10)0.0384 (10)0.6107 (7)0.09690.272 (7)
C2310.3301 (3)0.1888 (3)0.5483 (2)0.07360.728 (7)
C2410.2840 (3)0.0737 (3)0.54184 (18)0.09070.728 (7)
C2510.1716 (5)0.0191 (4)0.5286 (4)0.12790.728 (7)
C2610.3410 (5)0.0437 (4)0.4932 (3)0.10870.728 (7)
C310.6670 (2)0.4121 (3)0.57097 (12)0.0647
C320.6922 (2)0.4400 (3)0.50194 (13)0.0692
C330.7766 (3)0.4200 (3)0.48021 (15)0.0844
C3400.7886 (7)0.4150 (10)0.4082 (3)0.10420.235 (14)
C3500.8907 (13)0.427 (2)0.3893 (4)0.11070.235 (14)
C3600.7663 (19)0.4883 (18)0.3713 (5)0.10860.235 (14)
C3410.8028 (3)0.4361 (4)0.4100 (2)0.10190.765 (14)
C3510.8816 (5)0.4067 (7)0.3908 (3)0.11220.765 (14)
C3610.8325 (8)0.5404 (7)0.3879 (3)0.12210.765 (14)
C410.5799 (2)0.4083 (3)0.66950 (13)0.0702
C4210.4941 (5)0.3990 (7)0.7027 (2)0.06290.451 (8)
C4310.4846 (5)0.3504 (5)0.7677 (2)0.06260.451 (8)
C4410.4185 (4)0.3629 (4)0.8146 (2)0.06220.451 (8)
C4510.4193 (6)0.3197 (7)0.8796 (3)0.07990.451 (8)
C4610.3111 (5)0.3227 (7)0.7909 (3)0.06970.451 (8)
C4200.5196 (5)0.4493 (6)0.7114 (2)0.07120.549 (8)
C4300.4995 (4)0.4038 (5)0.7788 (2)0.08800.549 (8)
C4400.4069 (5)0.2967 (5)0.7861 (3)0.09580.549 (8)
C4500.3956 (6)0.2539 (8)0.8534 (4)0.11180.549 (8)
C4600.3084 (5)0.2896 (7)0.7634 (4)0.09910.549 (8)
H1110.55440.54710.60670.0670*
H1120.60290.54620.54250.0656*
H1210.71530.60670.65720.0791*
H1220.76440.61350.58930.0793*
H1310.68740.73560.63600.0859*
H1320.69050.72670.56220.0854*
H1410.87170.80040.57440.1021*
H1510.90740.96970.59200.1558*
H1520.79590.92390.62120.1561*
H1530.80860.90930.54730.1558*
H1610.95020.87870.66620.1585*
H1620.84170.82580.70000.1589*
H1630.88660.75750.67320.1584*
H2110.43330.37670.58560.0742*
H2120.48720.38040.52070.0733*
H2210.42720.22710.61530.0902*0.272 (7)
H2220.48890.23040.55370.0899*0.272 (7)
H23010.32330.23650.51460.1172*0.272 (7)
H23020.34930.14980.49910.1172*0.272 (7)
H24010.23340.15360.60310.1391*0.272 (7)
H25010.11000.01430.54510.1700*0.272 (7)
H25020.11010.08910.53570.1701*0.272 (7)
H25030.16850.05750.48640.1700*0.272 (7)
H26010.24410.03970.65340.1409*0.272 (7)
H26020.33400.05670.60950.1408*0.272 (7)
H26030.22330.02850.59450.1410*0.272 (7)
H2230.44520.22950.61500.0902*0.728 (7)
H2240.47900.22750.54540.0894*0.728 (7)
H23110.29040.20600.57490.0886*0.728 (7)
H23120.32870.21120.50650.0890*0.728 (7)
H24110.28950.04740.58390.1099*0.728 (7)
H25110.14840.05230.51930.1930*0.728 (7)
H25120.13590.02180.56730.1931*0.728 (7)
H25130.15880.05070.49220.1930*0.728 (7)
H26110.31510.02980.49500.1651*0.728 (7)
H26120.41290.07900.50130.1653*0.728 (7)
H26130.33080.06110.45020.1652*0.728 (7)
H3110.72730.45200.59730.0777*
H3120.64360.33980.57680.0780*
H3210.71610.51210.49680.0830*
H3220.63170.40130.47550.0832*
H3310.84160.47290.49780.1010*0.235 (14)
H3320.76160.35380.49750.1011*0.235 (14)
H34010.73670.34560.39380.1250*0.235 (14)
H35010.87720.36710.35780.1659*0.235 (14)
H35020.93100.49880.36640.1659*0.235 (14)
H35030.92790.42480.43100.1660*0.235 (14)
H36010.83720.53940.34210.1620*0.235 (14)
H36020.75120.53200.40870.1620*0.235 (14)
H36030.69730.43890.34080.1620*0.235 (14)
H3330.84100.46800.50510.1010*0.765 (14)
H3340.75830.34990.49060.1016*0.765 (14)
H34110.73620.38940.38560.1232*0.765 (14)
H35110.89470.41760.34560.1669*0.765 (14)
H35120.94550.44660.41270.1670*0.765 (14)
H35130.85740.33550.39850.1667*0.765 (14)
H36110.86770.55300.34710.1837*0.765 (14)
H36120.87560.59000.41890.1838*0.765 (14)
H36130.77050.54350.38100.1842*0.765 (14)
H4110.64370.46010.68820.0839*0.488 (8)
H4120.57460.34170.67440.0838*0.488 (8)
H42110.50630.46710.70980.0752*0.451 (8)
H42120.43140.36170.67740.0760*0.451 (8)
H43110.55310.38220.78640.0761*0.451 (8)
H43120.45980.27850.76090.0761*0.451 (8)
H44110.44580.43530.82060.0746*0.451 (8)
H45110.36580.31870.90590.1207*0.451 (8)
H45120.48500.36240.89910.1210*0.451 (8)
H45130.40750.25160.87560.1211*0.451 (8)
H46110.27010.32960.82360.1047*0.451 (8)
H46120.28320.25200.77970.1044*0.451 (8)
H46130.31250.36080.75320.1047*0.451 (8)
H4130.65060.44140.68370.0835*0.512 (8)
H4140.55000.33520.67630.0837*0.512 (8)
H42010.56180.52220.71420.0850*0.549 (8)
H42020.45520.43340.69120.0847*0.549 (8)
H43010.48780.44860.80570.1051*0.549 (8)
H43020.56070.40390.79400.1050*0.549 (8)
H44010.41910.25260.75650.1143*0.549 (8)
H45010.36690.18150.85240.1669*0.549 (8)
H45020.35120.26930.87870.1667*0.549 (8)
H45030.46130.28480.87420.1669*0.549 (8)
H46010.26010.21990.75570.1480*0.549 (8)
H46020.28260.31580.79550.1482*0.549 (8)
H46030.31920.32690.72450.1479*0.549 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.05383 (18)0.1000 (3)0.06365 (19)0.04236 (18)0.00084 (13)0.01809 (16)
N10.0543 (12)0.0671 (14)0.0655 (13)0.0362 (11)0.0038 (10)0.0074 (11)
C110.0595 (16)0.0649 (17)0.0546 (15)0.0389 (14)0.0084 (12)0.0027 (13)
C120.0685 (19)0.070 (2)0.0667 (17)0.0412 (17)0.0158 (15)0.0052 (15)
C130.080 (2)0.067 (2)0.075 (2)0.0423 (18)0.0225 (18)0.0114 (16)
C140.091 (3)0.073 (2)0.089 (3)0.039 (2)0.020 (2)0.002 (2)
C150.120 (4)0.070 (3)0.110 (3)0.038 (3)0.038 (3)0.007 (2)
C160.101 (3)0.081 (3)0.122 (4)0.034 (3)0.048 (3)0.009 (3)
C210.0563 (15)0.0679 (15)0.0657 (15)0.0345 (12)0.0042 (12)0.0035 (13)
C220.076 (2)0.0672 (17)0.0778 (19)0.0332 (16)0.0108 (17)0.0090 (15)
C2300.095 (5)0.084 (6)0.086 (6)0.022 (5)0.023 (5)0.022 (5)
C2400.112 (6)0.090 (6)0.107 (6)0.016 (5)0.024 (5)0.027 (5)
C2500.112 (8)0.085 (8)0.115 (8)0.026 (7)0.025 (7)0.025 (7)
C2600.103 (8)0.066 (6)0.086 (7)0.016 (6)0.025 (6)0.018 (6)
C2310.072 (3)0.069 (3)0.059 (2)0.020 (2)0.001 (2)0.007 (2)
C2410.101 (3)0.060 (2)0.076 (3)0.014 (2)0.013 (2)0.006 (2)
C2510.107 (4)0.091 (4)0.119 (5)0.000 (4)0.015 (4)0.004 (4)
C2610.119 (5)0.073 (3)0.120 (4)0.037 (3)0.009 (4)0.002 (3)
C310.0572 (15)0.0610 (16)0.0839 (17)0.0356 (13)0.0019 (13)0.0048 (15)
C320.0604 (15)0.0688 (18)0.0818 (18)0.0348 (14)0.0004 (14)0.0093 (15)
C330.079 (2)0.0601 (17)0.117 (2)0.0366 (16)0.0243 (19)0.0037 (18)
C3400.104 (6)0.071 (5)0.124 (5)0.034 (5)0.037 (6)0.007 (5)
C3500.105 (8)0.079 (8)0.129 (9)0.031 (7)0.040 (8)0.020 (8)
C3600.113 (8)0.071 (7)0.127 (8)0.035 (7)0.049 (7)0.003 (7)
C3410.088 (3)0.104 (3)0.117 (3)0.050 (3)0.022 (3)0.023 (3)
C3510.080 (4)0.109 (5)0.141 (5)0.042 (4)0.030 (4)0.025 (4)
C3610.119 (5)0.118 (4)0.127 (5)0.057 (4)0.030 (4)0.011 (4)
C410.0549 (15)0.092 (2)0.0662 (16)0.0381 (15)0.0039 (13)0.0171 (15)
C4210.057 (3)0.071 (4)0.056 (3)0.029 (3)0.008 (3)0.008 (3)
C4310.067 (3)0.070 (4)0.051 (3)0.034 (3)0.014 (3)0.002 (3)
C4410.074 (3)0.075 (4)0.047 (3)0.044 (3)0.007 (2)0.003 (3)
C4510.098 (5)0.088 (5)0.051 (3)0.045 (4)0.010 (3)0.012 (3)
C4610.070 (4)0.085 (5)0.054 (4)0.038 (4)0.006 (3)0.002 (3)
C4200.054 (3)0.107 (4)0.059 (3)0.045 (3)0.003 (2)0.005 (3)
C4300.085 (4)0.121 (5)0.057 (3)0.051 (4)0.005 (3)0.001 (3)
C4400.101 (4)0.122 (5)0.074 (3)0.062 (4)0.009 (3)0.015 (4)
C4500.116 (5)0.142 (7)0.089 (5)0.073 (5)0.006 (4)0.029 (5)
C4600.094 (5)0.119 (6)0.083 (5)0.052 (4)0.007 (4)0.021 (4)
Geometric parameters (Å, º) top
N1—C111.526 (4)C33—C3401.524 (7)
N1—C211.524 (3)C33—H3310.978
N1—C311.521 (3)C33—H3320.979
N1—C411.516 (3)C33—C3411.509 (5)
C11—C121.510 (5)C33—H3331.021
C11—H1110.975C33—H3340.977
C11—H1120.954C340—C3501.514 (7)
C12—C131.519 (5)C340—C3601.521 (7)
C12—H1210.989C340—H34010.993
C12—H1220.983C350—H35011.058
C13—C141.512 (6)C350—H35021.055
C13—H1310.978C350—H35031.049
C13—H1320.953C360—H36011.137
C14—C151.517 (6)C360—H36021.120
C14—C161.478 (6)C360—H36031.130
C14—H1410.970C341—C3511.520 (5)
C15—H1510.984C341—C3611.483 (6)
C15—H1520.982C341—H34111.031
C15—H1530.963C351—H35110.962
C16—H1610.974C351—H35120.963
C16—H1620.961C351—H35130.963
C16—H1630.971C361—H36110.974
C21—C221.510 (3)C361—H36120.959
C21—H2110.962C361—H36130.974
C21—H2120.973C41—C4211.416 (5)
C22—C2301.542 (7)C41—H4110.972
C22—H2210.975C41—H4120.976
C22—H2220.965C41—C4201.597 (5)
C22—C2311.511 (5)C41—H4130.975
C22—H2230.985C41—H4140.975
C22—H2240.945C421—C4311.518 (5)
C230—C2401.536 (7)C421—H42110.963
C230—H23010.959C421—H42120.982
C230—H23020.968C431—C4411.480 (6)
C240—C2501.517 (7)C431—H43110.980
C240—C2601.522 (7)C431—H43120.968
C240—H24010.992C441—C4511.511 (5)
C250—H25010.969C441—C4611.506 (6)
C250—H25020.965C441—H44110.966
C250—H25030.966C451—H45110.973
C260—H26010.946C451—H45120.965
C260—H26020.955C451—H45130.958
C260—H26030.946C461—H46110.965
C231—C2411.524 (5)C461—H46120.962
C231—H23110.948C461—H46130.971
C231—H23120.942C420—C4301.532 (5)
C241—C2511.499 (6)C420—H42010.961
C241—C2611.541 (6)C420—H42020.975
C241—H24110.988C430—C4401.530 (6)
C251—H25110.974C430—H43010.964
C251—H25120.985C430—H43020.978
C251—H25130.971C440—C4501.524 (6)
C261—H26110.977C440—C4601.516 (6)
C261—H26120.958C440—H44010.993
C261—H26130.971C450—H45010.956
C31—C321.500 (3)C450—H45020.971
C31—H3110.975C450—H45030.965
C31—H3120.975C460—H46010.949
C32—C331.522 (3)C460—H46020.957
C32—H3210.968C460—H46030.958
C32—H3220.975
C11—N1—C21106.09 (17)C32—C33—C340115.95 (7)
C11—N1—C31110.2 (2)C32—C33—H331108.9
C21—N1—C31111.9 (2)C340—C33—H331108.4
C11—N1—C41109.2 (2)C32—C33—H332107.7
C21—N1—C41112.9 (2)C340—C33—H332106.8
C31—N1—C41106.47 (12)H331—C33—H332108.9
N1—C11—C12115.9 (2)C32—C33—C341115.92 (7)
N1—C11—H111108.8C32—C33—H333107.7
C12—C11—H111109.2C341—C33—H333107.5
N1—C11—H112107.3C32—C33—H334109.9
C12—C11—H112109.7C341—C33—H334107.5
H111—C11—H112105.4H333—C33—H334108.1
C11—C12—C13110.5 (3)C33—C340—C350113.05 (7)
C11—C12—H121107.9C33—C340—C360113.07 (7)
C13—C12—H121111.8C350—C340—C360111.25 (7)
C11—C12—H122109.0C33—C340—H3401107.6
C13—C12—H122110.8C350—C340—H3401105.5
H121—C12—H122106.7C360—C340—H3401105.7
C12—C13—C14115.1 (3)C340—C350—H3501108.2
C12—C13—H131105.6C340—C350—H3502106.0
C14—C13—H131104.6H3501—C350—H3502111.3
C12—C13—H132111.0C340—C350—H3503108.2
C14—C13—H132112.6H3501—C350—H3503111.3
H131—C13—H132107.1H3502—C350—H3503111.6
C13—C14—C15110.7 (4)C340—C360—H3601107.0
C13—C14—C16114.4 (4)C340—C360—H3602105.0
C15—C14—C16111.8 (4)H3601—C360—H3602112.1
C13—C14—H141106.9C340—C360—H3603105.8
C15—C14—H141108.4H3601—C360—H3603113.1
C16—C14—H141104.2H3602—C360—H3603113.1
C14—C15—H151110.4C33—C341—C351113.06 (7)
C14—C15—H152107.1C33—C341—C361113.08 (7)
H151—C15—H152108.1C351—C341—C361111.28 (7)
C14—C15—H153110.5C33—C341—H3411106.5
H151—C15—H153111.2C351—C341—H3411107.9
H152—C15—H153109.4C361—C341—H3411104.4
C14—C16—H161108.2C341—C351—H3511109.6
C14—C16—H162106.9C341—C351—H3512112.3
H161—C16—H162110.3H3511—C351—H3512107.7
C14—C16—H163109.6C341—C351—H3513111.6
H161—C16—H163110.3H3511—C351—H3513106.7
H162—C16—H163111.5H3512—C351—H3513108.6
N1—C21—C22115.72 (5)C341—C361—H3611109.2
N1—C21—H211105.6C341—C361—H3612110.3
C22—C21—H211108.7H3611—C361—H3612110.5
N1—C21—H212108.5C341—C361—H3613108.1
C22—C21—H212109.6H3611—C361—H3613107.8
H211—C21—H212108.5H3612—C361—H3613110.9
C21—C22—C230110.58 (7)N1—C41—C421115.98 (7)
C21—C22—H221109.0N1—C41—H411108.5
C230—C22—H221109.3C421—C41—H411112.0
C21—C22—H222110.0N1—C41—H412106.6
C230—C22—H222109.0C421—C41—H412104.4
H221—C22—H222108.8H411—C41—H412109.0
C21—C22—C231110.57 (7)N1—C41—C420115.47 (7)
C21—C22—H223109.4N1—C41—H413106.4
C231—C22—H223110.4C420—C41—H413109.1
C21—C22—H224110.7N1—C41—H414108.7
C231—C22—H224108.9C420—C41—H414109.3
H223—C22—H224106.8H413—C41—H414107.6
C22—C230—C240116.03 (7)C41—C421—C431110.34 (7)
C22—C230—H2301108.1C41—C421—H4211107.1
C240—C230—H2301106.5C431—C421—H4211107.5
C22—C230—H2302108.5C41—C421—H4212111.5
C240—C230—H2302107.3C431—C421—H4212111.9
H2301—C230—H2302110.2H4211—C421—H4212108.2
C230—C240—C250113.02 (7)C421—C431—C441116.02 (7)
C230—C240—C260113.10 (7)C421—C431—H4311107.5
C250—C240—C260111.23 (7)C441—C431—H4311106.7
C230—C240—H2401106.0C421—C431—H4312107.6
C250—C240—H2401107.9C441—C431—H4312109.6
C260—C240—H2401104.9H4311—C431—H4312109.3
C240—C250—H2501109.9C431—C441—C451112.96 (7)
C240—C250—H2502108.3C431—C441—C461112.97 (7)
H2501—C250—H2502109.0C451—C441—C461111.23 (7)
C240—C250—H2503109.9C431—C441—H4411107.3
H2501—C250—H2503110.0C451—C441—H4411106.5
H2502—C250—H2503109.8C461—C441—H4411105.3
C240—C260—H2601108.8C441—C451—H4511109.3
C240—C260—H2602111.1C441—C451—H4512108.6
H2601—C260—H2602109.5H4511—C451—H4512110.0
C240—C260—H2603109.5C441—C451—H4513110.5
H2601—C260—H2603108.5H4511—C451—H4513109.1
H2602—C260—H2603109.4H4512—C451—H4513109.4
C22—C231—C241115.87 (7)C441—C461—H4611110.1
C22—C231—H2311108.7C441—C461—H4612108.4
C241—C231—H2311112.1H4611—C461—H4612110.1
C22—C231—H2312106.9C441—C461—H4613109.3
C241—C231—H2312104.5H4611—C461—H4613109.7
H2311—C231—H2312108.4H4612—C461—H4613109.3
C231—C241—C251113.03 (7)C41—C420—C430110.73 (7)
C231—C241—C261113.03 (7)C41—C420—H4201107.3
C251—C241—C261111.26 (7)C430—C420—H4201109.2
C231—C241—H2411107.5C41—C420—H4202111.1
C251—C241—H2411104.1C430—C420—H4202109.8
C261—C241—H2411107.3H4201—C420—H4202108.6
C241—C251—H2511109.2C420—C430—C440116.01 (7)
C241—C251—H2512108.7C420—C430—H4301106.6
H2511—C251—H2512108.0C440—C430—H4301107.0
C241—C251—H2513108.9C420—C430—H4302109.0
H2511—C251—H2513109.9C440—C430—H4302109.6
H2512—C251—H2513112.0H4301—C430—H4302108.3
C241—C261—H2611110.2C430—C440—C450113.01 (7)
C241—C261—H2612111.4C430—C440—C460113.08 (7)
H2611—C261—H2612109.0C450—C440—C460111.22 (7)
C241—C261—H2613110.2C430—C440—H4401105.6
H2611—C261—H2613108.4C450—C440—H4401108.0
H2612—C261—H2613107.6C460—C440—H4401105.3
N1—C31—C32115.62 (5)C440—C450—H4501111.0
N1—C31—H311106.7C440—C450—H4502110.3
C32—C31—H311110.1H4501—C450—H4502108.2
N1—C31—H312105.6C440—C450—H4503110.0
C32—C31—H312109.6H4501—C450—H4503109.4
H311—C31—H312109.0H4502—C450—H4503107.8
C31—C32—C33110.61 (5)C440—C460—H4601108.3
C31—C32—H321108.9C440—C460—H4602109.9
C33—C32—H321108.2H4601—C460—H4602109.5
C31—C32—H322110.3C440—C460—H4603110.6
C33—C32—H322109.9H4601—C460—H4603108.6
H321—C32—H322108.9H4602—C460—H4603109.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C230—H2302···C2610.971.552.346 (11)136
C250—H2502···C250i0.972.052.784 (11)131
C260—H2601···C260ii0.951.802.552 (11)134
Symmetry codes: (i) y, x, z+1; (ii) xy, y, z+4/3.

Experimental details

(I_100KQ)(I_250K)(I_100KC)
Crystal data
Chemical formulaC24H52N+·BrC24H52N+·BrC24H52N+·Br
Mr434.59434.59434.59
Crystal system, space groupTrigonal, P3221Trigonal, P3221Trigonal, P3221
Temperature (K)100250100
a, c (Å)15.12762 (13), 21.0223 (2)15.4995 (2), 21.1346 (3)15.1327 (3), 20.9326 (4)
V3)4166.31 (6)4397.06 (12)4151.30 (13)
Z666
Radiation typeCu KαCu KαCu Kα
µ (mm1)2.041.932.05
Crystal size (mm)0.15 × 0.14 × 0.070.15 × 0.14 × 0.070.15 × 0.14 × 0.07
Data collection
DiffractometerOxford SuperNova Dual
diffractometer with Cu at zero and Atlas detector
Oxford SuperNova Dual
diffractometer with Cu at zero and Atlas detector
Oxford SuperNova Dual
diffractometer with Cu at zero and Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2011)
Multi-scan
(CrysAlis PRO; Agilent, 2011)
Multi-scan
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.57, 0.870.60, 0.870.59, 0.87
No. of measured, independent and
observed [I > 2σ(I)] reflections
89102, 5781, 5591 94951, 6128, 4391 88138, 5768, 5336
Rint0.0330.0370.040
(sin θ/λ)max1)0.6310.6320.631
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.114, 1.02 0.049, 0.178, 0.96 0.041, 0.128, 0.98
No. of reflections578161285768
No. of parameters347366347
No. of restraints648864648
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.600.21, 0.240.42, 0.44
Absolute structureFlack (1983), with 2550 Friedel pairsFlack (1983), with 2710 Friedel pairsFlack (1983), with 2546 Friedel pairs
Absolute structure parameter0.02 (2)0.03 (3)0.01 (3)

Computer programs: CrysAlis PRO (Agilent, 2011), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996).

 

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