Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042274/er2039sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042274/er2039Isup2.hkl |
CCDC reference: 663675
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.077
- Data-to-parameter ratio = 34.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT480_ALERT_4_B Long H...A H-Bond Reported H35 .. BR1 .. 3.42 Ang. PLAT480_ALERT_4_B Long H...A H-Bond Reported H2A .. BR1 .. 3.43 Ang.
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H33 .. BR1 .. 3.02 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H36 .. BR1 .. 3.13 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2C .. BR1 .. 3.12 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B .. BR1 .. 3.04 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A .. BR1 .. 3.19 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B .. BR1 .. 3.14 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. BR1 .. 3.13 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A .. BR1 .. 3.26 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C11 .. BR1 .. 4.10 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C11 .. BR1 .. 4.22 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C35 .. BR1 .. 4.12 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C2 .. BR1 .. 4.24 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C12 .. CG1 .. 4.11 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 15 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Hodorowicz et al. (2003, 2005); Kwolek et al. (2003); Kruger et al. (2003); Allen et al. (1987).
The title compoud was prepared by dissolving a (1:1) mixture of benzyl bromide [CH3(CH2)3Br] and N,N-dimethylbenzylamine [C6H5CH2N(CH3)2] in acetone at 273 K. The solution was slowly heated to room temperature to give colourless single crystals of the title compound. Recrystallization from acetone afforded crystals suitable for X-ray measurements.
All hydrogen atom positions were observed in difference Fourier map. Nevertheless, in the refinement procedure the hydrogen atoms were positioned geometrically and refined using a riding model (including free rotation about the C—C bond), with C—H = 0.95–0.99 Å (C—H = 0.97 Å for CH2 groups, 0.96 Å for CH3 groups, and 0.93 Å for aromatic CH) and with Uiso(H) = 1.5Ueq(C) for methyl groups and Uiso(H) = 1.2Ueq(C) for all other H atoms.
Ammonium halides are widely studied cationic surfactants used in many fields such as micelar catalysis, medicine, detergency. Additionally they are able to change the nature of the surface of clay minerals, such as montmorillonite or bentonite, from hydrophilic to hydrophobic one (Kwolek et al., 2003). The title compound was investigated in the project on relationship between sorption properties of montmorillonite and the architecture of hydrophobic layers which are due to modifications of the clay mineral by, in this case, quaternary alkylammonium salts (Hodorowicz et al., 2003, 2005). The crystal structure analysis of benzyldimethylbutylammonium bromide was performed to find out the influence of molecular geometry on the packing properties of the ammonium cations. The molecular structure of the title compound is shown in Fig. 1. The symmetrically independent part of the unit cell is composed of the ammonium cation, showing pseudosymmetry m, and bromide counterion (N+···Br- = 4.287 (2) Å). The bond lengths and angles indicate the typical tetrahedral arragement of substituents at the N atom. The benzene rings are essentially planar, with a mean deviation of the C atoms from the best plane of 0.006 Å. The molecular dimensions are comparable with the values reported in the literature (Allen et al., 1987). Methyl and methylene groups as well as C—H of C31–C36 benzene ring of the quaternary ammonium cation are involved in weak intermolecular hydrogen interactions of C—H···Br- type (Table 1). This kind of interactions are responsible for self-assembly of ammonium cations in hydrophobic layers (Hodorowicz et al., 2003, 2005). The ammonium cations are packed in a pseudo-tetragonal `parquet'-style pattern, with Br- ions in between (Fig. 2).
For related literature, see: Hodorowicz et al. (2003, 2005); Kwolek et al. (2003); Kruger et al. (2003); Allen et al. (1987).
Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997) and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C13H22N+·Br− | F(000) = 568 |
Mr = 272.23 | Dx = 1.313 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4362 reflections |
a = 8.924 (2) Å | θ = 1.0–32.0° |
b = 9.046 (2) Å | µ = 2.96 mm−1 |
c = 17.183 (4) Å | T = 293 K |
β = 96.787 (1)° | Prism, colourless |
V = 1377.4 (5) Å3 | 0.25 × 0.22 × 0.20 mm |
Z = 4 |
Nonius KappaCCD area-detector diffractometer | 4725 independent reflections |
Radiation source: fine-focus sealed tube | 3058 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.021 |
Detector resolution: 9 pixels mm-1 | θmax = 32.0°, θmin = 3.5° |
φ and ω scans to fill the asymmetric unit | h = 0→13 |
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997) | k = −13→12 |
Tmin = 0.493, Tmax = 0.554 | l = −25→25 |
7959 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0084P)2 + 0.6796P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
4725 reflections | Δρmax = 0.36 e Å−3 |
137 parameters | Δρmin = −0.45 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0556 (12) |
C13H22N+·Br− | V = 1377.4 (5) Å3 |
Mr = 272.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.924 (2) Å | µ = 2.96 mm−1 |
b = 9.046 (2) Å | T = 293 K |
c = 17.183 (4) Å | 0.25 × 0.22 × 0.20 mm |
β = 96.787 (1)° |
Nonius KappaCCD area-detector diffractometer | 4725 independent reflections |
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997) | 3058 reflections with I > 2σ(I) |
Tmin = 0.493, Tmax = 0.554 | Rint = 0.021 |
7959 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.36 e Å−3 |
4725 reflections | Δρmin = −0.45 e Å−3 |
137 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.01487 (2) | 0.00013 (2) | 0.241455 (12) | 0.04883 (9) | |
N1 | −0.06917 (17) | 0.45897 (17) | 0.19138 (10) | 0.0387 (3) | |
C1 | −0.0634 (2) | 0.4635 (2) | 0.28006 (12) | 0.0433 (4) | |
H1A | −0.1634 | 0.4870 | 0.2932 | 0.052* | |
H1B | −0.0377 | 0.3656 | 0.3005 | 0.052* | |
C11 | 0.0478 (2) | 0.5733 (2) | 0.32121 (13) | 0.0505 (5) | |
H11A | 0.1494 | 0.5470 | 0.3116 | 0.061* | |
H11B | 0.0261 | 0.6714 | 0.3000 | 0.061* | |
C12 | 0.0385 (2) | 0.5749 (2) | 0.40864 (13) | 0.0510 (5) | |
H12A | 0.0583 | 0.4763 | 0.4296 | 0.061* | |
H12B | −0.0628 | 0.6027 | 0.4181 | 0.061* | |
C13 | 0.1511 (3) | 0.6825 (3) | 0.45093 (16) | 0.0700 (7) | |
H13A | 0.1421 | 0.6807 | 0.5060 | 0.084* | |
H13B | 0.1306 | 0.7804 | 0.4310 | 0.084* | |
H13C | 0.2515 | 0.6542 | 0.4425 | 0.084* | |
C2 | −0.1167 (3) | 0.6065 (2) | 0.15765 (13) | 0.0539 (5) | |
H2A | −0.2139 | 0.6318 | 0.1724 | 0.065* | |
H2B | −0.1223 | 0.6025 | 0.1016 | 0.065* | |
H2C | −0.0444 | 0.6800 | 0.1773 | 0.065* | |
C3 | −0.1856 (2) | 0.3414 (2) | 0.16165 (11) | 0.0418 (4) | |
H3A | −0.1579 | 0.2488 | 0.1880 | 0.050* | |
H3B | −0.2831 | 0.3705 | 0.1762 | 0.050* | |
C31 | −0.2008 (2) | 0.3157 (2) | 0.07474 (12) | 0.0412 (4) | |
C32 | −0.3044 (2) | 0.3941 (2) | 0.02355 (13) | 0.0513 (5) | |
H32 | −0.3641 | 0.4661 | 0.0432 | 0.062* | |
C33 | −0.3195 (3) | 0.3662 (3) | −0.05597 (14) | 0.0580 (6) | |
H33 | −0.3889 | 0.4196 | −0.0895 | 0.070* | |
C34 | −0.2324 (3) | 0.2596 (3) | −0.08580 (14) | 0.0581 (6) | |
H34 | −0.2424 | 0.2415 | −0.1394 | 0.070* | |
C35 | −0.1303 (3) | 0.1797 (2) | −0.03612 (14) | 0.0568 (5) | |
H35 | −0.0712 | 0.1078 | −0.0563 | 0.068* | |
C36 | −0.1154 (2) | 0.2061 (2) | 0.04369 (13) | 0.0488 (5) | |
H36 | −0.0477 | 0.1503 | 0.0770 | 0.059* | |
C4 | 0.0826 (2) | 0.4170 (3) | 0.16919 (13) | 0.0513 (5) | |
H4A | 0.1114 | 0.3222 | 0.1913 | 0.062* | |
H4B | 0.1557 | 0.4897 | 0.1889 | 0.062* | |
H4C | 0.0780 | 0.4121 | 0.1132 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.04368 (12) | 0.04684 (12) | 0.05522 (14) | −0.00025 (9) | 0.00274 (8) | 0.00673 (10) |
N1 | 0.0350 (7) | 0.0334 (7) | 0.0490 (9) | −0.0011 (6) | 0.0100 (7) | 0.0040 (6) |
C1 | 0.0405 (9) | 0.0443 (11) | 0.0461 (10) | 0.0012 (8) | 0.0094 (8) | 0.0048 (8) |
C11 | 0.0519 (12) | 0.0452 (11) | 0.0550 (12) | −0.0024 (9) | 0.0091 (10) | 0.0024 (10) |
C12 | 0.0480 (11) | 0.0482 (12) | 0.0582 (13) | 0.0042 (9) | 0.0113 (10) | −0.0054 (10) |
C13 | 0.0710 (16) | 0.0664 (16) | 0.0727 (17) | −0.0093 (13) | 0.0084 (13) | −0.0159 (14) |
C2 | 0.0680 (14) | 0.0359 (10) | 0.0570 (13) | −0.0008 (10) | 0.0050 (11) | 0.0069 (9) |
C3 | 0.0368 (9) | 0.0366 (9) | 0.0537 (11) | −0.0034 (7) | 0.0123 (8) | 0.0048 (8) |
C31 | 0.0357 (9) | 0.0374 (9) | 0.0513 (11) | −0.0043 (7) | 0.0086 (8) | 0.0027 (8) |
C32 | 0.0413 (10) | 0.0487 (12) | 0.0637 (14) | 0.0025 (9) | 0.0055 (10) | 0.0053 (10) |
C33 | 0.0528 (12) | 0.0591 (14) | 0.0598 (14) | −0.0068 (10) | −0.0037 (10) | 0.0109 (11) |
C34 | 0.0647 (14) | 0.0581 (14) | 0.0523 (13) | −0.0205 (11) | 0.0101 (11) | −0.0015 (11) |
C35 | 0.0617 (13) | 0.0462 (12) | 0.0647 (14) | −0.0051 (10) | 0.0165 (11) | −0.0089 (11) |
C36 | 0.0493 (11) | 0.0384 (10) | 0.0590 (13) | 0.0021 (8) | 0.0079 (9) | 0.0001 (9) |
C4 | 0.0375 (10) | 0.0581 (13) | 0.0610 (13) | −0.0043 (9) | 0.0174 (9) | −0.0032 (11) |
N1—C2 | 1.496 (2) | C2—H2C | 0.9600 |
N1—C4 | 1.499 (2) | C3—C31 | 1.501 (3) |
N1—C1 | 1.519 (2) | C3—H3A | 0.9700 |
N1—C3 | 1.532 (2) | C3—H3B | 0.9700 |
N1—Br1 | 4.287 (2) | C31—C32 | 1.392 (3) |
C1—C11 | 1.518 (3) | C31—C36 | 1.395 (3) |
C1—H1A | 0.9700 | C32—C33 | 1.380 (3) |
C1—H1B | 0.9700 | C32—H32 | 0.9300 |
C11—C12 | 1.515 (3) | C33—C34 | 1.375 (3) |
C11—H11A | 0.9700 | C33—H33 | 0.9300 |
C11—H11B | 0.9700 | C34—C35 | 1.378 (3) |
C12—C13 | 1.520 (3) | C34—H34 | 0.9300 |
C12—H12A | 0.9700 | C35—C36 | 1.383 (3) |
C12—H12B | 0.9700 | C35—H35 | 0.9300 |
C13—H13A | 0.9600 | C36—H36 | 0.9300 |
C13—H13B | 0.9600 | C4—H4A | 0.9600 |
C13—H13C | 0.9600 | C4—H4B | 0.9600 |
C2—H2A | 0.9600 | C4—H4C | 0.9600 |
C2—H2B | 0.9600 | ||
C2—N1—C4 | 110.54 (16) | N1—C2—H2B | 109.5 |
C2—N1—C1 | 109.82 (15) | H2A—C2—H2B | 109.5 |
C4—N1—C1 | 109.70 (15) | N1—C2—H2C | 109.5 |
C2—N1—C3 | 109.90 (15) | H2A—C2—H2C | 109.5 |
C4—N1—C3 | 109.68 (15) | H2B—C2—H2C | 109.5 |
C1—N1—C3 | 107.14 (14) | C31—C3—N1 | 114.67 (14) |
C2—N1—Br1 | 167.48 (12) | C31—C3—H3A | 108.6 |
C4—N1—Br1 | 70.35 (10) | N1—C3—H3A | 108.6 |
C1—N1—Br1 | 80.81 (9) | C31—C3—H3B | 108.6 |
C3—N1—Br1 | 59.34 (9) | N1—C3—H3B | 108.6 |
C11—C1—N1 | 115.32 (16) | H3A—C3—H3B | 107.6 |
C11—C1—H1A | 108.4 | C32—C31—C36 | 118.2 (2) |
N1—C1—H1A | 108.4 | C32—C31—C3 | 121.68 (18) |
C11—C1—H1B | 108.4 | C36—C31—C3 | 120.06 (18) |
N1—C1—H1B | 108.4 | C33—C32—C31 | 120.8 (2) |
H1A—C1—H1B | 107.5 | C33—C32—H32 | 119.6 |
C12—C11—C1 | 111.03 (17) | C31—C32—H32 | 119.6 |
C12—C11—H11A | 109.4 | C34—C33—C32 | 120.2 (2) |
C1—C11—H11A | 109.4 | C34—C33—H33 | 119.9 |
C12—C11—H11B | 109.4 | C32—C33—H33 | 119.9 |
C1—C11—H11B | 109.4 | C33—C34—C35 | 119.9 (2) |
H11A—C11—H11B | 108.0 | C33—C34—H34 | 120.0 |
C11—C12—C13 | 111.7 (2) | C35—C34—H34 | 120.0 |
C11—C12—H12A | 109.3 | C34—C35—C36 | 120.2 (2) |
C13—C12—H12A | 109.3 | C34—C35—H35 | 119.9 |
C11—C12—H12B | 109.3 | C36—C35—H35 | 119.9 |
C13—C12—H12B | 109.3 | C35—C36—C31 | 120.6 (2) |
H12A—C12—H12B | 107.9 | C35—C36—H36 | 119.7 |
C12—C13—H13A | 109.5 | C31—C36—H36 | 119.7 |
C12—C13—H13B | 109.5 | N1—C4—H4A | 109.5 |
H13A—C13—H13B | 109.5 | N1—C4—H4B | 109.5 |
C12—C13—H13C | 109.5 | H4A—C4—H4B | 109.5 |
H13A—C13—H13C | 109.5 | N1—C4—H4C | 109.5 |
H13B—C13—H13C | 109.5 | H4A—C4—H4C | 109.5 |
N1—C2—H2A | 109.5 | H4B—C4—H4C | 109.5 |
C2—N1—C1—C11 | −61.3 (2) | N1—C3—C31—C32 | −90.8 (2) |
C4—N1—C1—C11 | 60.4 (2) | N1—C3—C31—C36 | 92.4 (2) |
C3—N1—C1—C11 | 179.40 (16) | C36—C31—C32—C33 | −1.4 (3) |
Br1—N1—C1—C11 | 125.59 (16) | C3—C31—C32—C33 | −178.28 (19) |
N1—C1—C11—C12 | 176.89 (17) | C31—C32—C33—C34 | 0.2 (3) |
C1—C11—C12—C13 | 179.01 (19) | C32—C33—C34—C35 | 0.4 (3) |
C2—N1—C3—C31 | 63.8 (2) | C33—C34—C35—C36 | 0.1 (3) |
C4—N1—C3—C31 | −58.0 (2) | C34—C35—C36—C31 | −1.4 (3) |
C1—N1—C3—C31 | −176.96 (15) | C32—C31—C36—C35 | 2.0 (3) |
Br1—N1—C3—C31 | −109.11 (16) | C3—C31—C36—C35 | 178.89 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···Br1 | 0.97 | 2.82 | 3.745 (2) | 160 |
C3—H3B···Br1i | 0.97 | 2.89 | 3.825 (2) | 162 |
C33—H33···Br1ii | 0.93 | 3.02 | 3.814 (2) | 145 |
C36—H36···Br1 | 0.93 | 3.13 | 3.929 (2) | 146 |
C2—H2C···Br1iii | 0.96 | 3.12 | 3.966 (2) | 148 |
C4—H4B···Br1iv | 0.96 | 3.04 | 3.811 (2) | 138 |
C4—H4A···Br1 | 0.96 | 3.19 | 4.038 (2) | 149 |
C11—H11B···Br1iii | 0.97 | 3.14 | 4.096 (2) | 170 |
C1—H1A···Br1i | 0.97 | 3.13 | 4.016 (2) | 153 |
C11—H11A···Br1iv | 0.97 | 3.26 | 4.222 (2) | 171 |
C35—H35···Br1v | 0.93 | 3.42 | 4.125 (2) | 134 |
C2—H2A···Br1i | 0.96 | 3.43 | 4.244 (2) | 144 |
C12—H12A···Cg1vi | 0.97 | 3.23 | 4.111 | 152 |
C12—H12B···Cg1vii | 0.97 | 3.10 | 3.980 | 151 |
Symmetry codes: (i) −x−1/2, y+1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x, y+1, z; (iv) −x+1/2, y+1/2, −z+1/2; (v) −x, −y, −z; (vi) x−1/2, −y−1/2, z−1/2; (vii) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C13H22N+·Br− |
Mr | 272.23 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 8.924 (2), 9.046 (2), 17.183 (4) |
β (°) | 96.787 (1) |
V (Å3) | 1377.4 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.96 |
Crystal size (mm) | 0.25 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector |
Absorption correction | Multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.493, 0.554 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7959, 4725, 3058 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.746 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.077, 1.08 |
No. of reflections | 4725 |
No. of parameters | 137 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.45 |
Computer programs: COLLECT (Nonius, 2000), SCALEPACK (Otwinowski & Minor, 1997) and DENZO (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1999) and Mercury (Macrae et al., 2006).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···Br1 | 0.97 | 2.82 | 3.745 (2) | 160.1 |
C3—H3B···Br1i | 0.97 | 2.89 | 3.825 (2) | 162.3 |
C33—H33···Br1ii | 0.93 | 3.02 | 3.814 (2) | 144.5 |
C36—H36···Br1 | 0.93 | 3.13 | 3.929 (2) | 145.6 |
C2—H2C···Br1iii | 0.96 | 3.12 | 3.966 (2) | 147.8 |
C4—H4B···Br1iv | 0.96 | 3.04 | 3.811 (2) | 138.2 |
C1—H1A···Br1i | 0.97 | 3.13 | 4.016 (2) | 153.4 |
C12—H12B···Cg1v | 0.97 | 3.10 | 3.980 | 151.3 |
Symmetry codes: (i) −x−1/2, y+1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x, y+1, z; (iv) −x+1/2, y+1/2, −z+1/2; (v) −x+3/2, y+1/2, −z+1/2. |
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Ammonium halides are widely studied cationic surfactants used in many fields such as micelar catalysis, medicine, detergency. Additionally they are able to change the nature of the surface of clay minerals, such as montmorillonite or bentonite, from hydrophilic to hydrophobic one (Kwolek et al., 2003). The title compound was investigated in the project on relationship between sorption properties of montmorillonite and the architecture of hydrophobic layers which are due to modifications of the clay mineral by, in this case, quaternary alkylammonium salts (Hodorowicz et al., 2003, 2005). The crystal structure analysis of benzyldimethylbutylammonium bromide was performed to find out the influence of molecular geometry on the packing properties of the ammonium cations. The molecular structure of the title compound is shown in Fig. 1. The symmetrically independent part of the unit cell is composed of the ammonium cation, showing pseudosymmetry m, and bromide counterion (N+···Br- = 4.287 (2) Å). The bond lengths and angles indicate the typical tetrahedral arragement of substituents at the N atom. The benzene rings are essentially planar, with a mean deviation of the C atoms from the best plane of 0.006 Å. The molecular dimensions are comparable with the values reported in the literature (Allen et al., 1987). Methyl and methylene groups as well as C—H of C31–C36 benzene ring of the quaternary ammonium cation are involved in weak intermolecular hydrogen interactions of C—H···Br- type (Table 1). This kind of interactions are responsible for self-assembly of ammonium cations in hydrophobic layers (Hodorowicz et al., 2003, 2005). The ammonium cations are packed in a pseudo-tetragonal `parquet'-style pattern, with Br- ions in between (Fig. 2).