organic compounds
of 4-amino-1-(4-methylbenzyl)pyridinium bromide
aDepartment of Physics, Shrimati Indira Gandhi College, Tiruchirappalli 620 002, Tamilnadu, India, bPG & Research Department of Physics, National College (Autonomous), Tiruchirappalli 620 001, Tamilnadu, India, cDepartment of Pharmaceutical Chemistry, PGP College of Pharmaceutical Science & Research Institute, Namakkal 637 207, India, dDrug Discovery and Developement Research Group, Department of Pharmaceutical Technology, Anna University Chennai, BIT Campus, Tiruchirappalli 620 024, Tamilnadu, India, and eX-ray Crystallography Division, CSIR–Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500 607, Andhra Pradesh, India
*Correspondence e-mail: 05.sharmi@gmail.com
The title molecular salt, C13H15N2+·Br−, crystallized with two independent ion pairs (A and B) in the In the cations, the planes of the pyridine and benzene rings are inclined to one another by 79.32 (8) and 82.30 (10)° in ion pairs A and B, respectively. In the crystal, the anions and cations are connected by N—H⋯Br hydrogen bonds, forming a centrosymmetric tetramer-like unit enclosing an R84(16) ring motif. These units are linked via C—H⋯Br hydrogen bonds, forming a three-dimensional network.
Keywords: crystal structure; molecular salt; pyridinium; bromide; hydrogen bonding.
CCDC reference: 1034948
1. Related literature
For the solid-phase synthesis of 1,3,5-trisubstituted pyridinium salts, see: Lago et al. (1998). For a review on quaternary pyridinium salts, see: Madaan & Tyagi (2008). For antimicrobial properties of quarternary amine derivatives, see: Thorsteinsson et al. (2003). For the pharmacological activity of 4-aminopyridine compounds, see: Hansebout & Blight (1996); Kumar & Rao (2005). For the antimicrobial activity of 4-aminopyridine compounds, see: Ilangovan et al. (2012); Sundararaman et al. (2013). For the crystal structures of related compounds, see: Seethalakshmi et al. (2006); Sundar et al. (2006a,b,c).
2. Experimental
2.1. Crystal data
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2.3. Refinement
|
Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 1034948
10.1107/S1600536814025343/su5023sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814025343/su5023Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814025343/su5023Isup3.cml
A mixture of 4-methylbenzylbromide (0.1 mol) and 4-aminopyridine (0.1 mol) in dry acetone (50 ml) was stirred at room temperature for 2–12 h. The pale yellow solid that separated was filtered off, washed with toluene, dried under vacuum to give the stable title molecular salt. It was recrystallized from chloroform-acetone (1:1, v/v), giving thin yellow plate-like crystals.
The N-bound H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were included in calculated positions and treated as riding atoms: C-H = 0.93 - 0.97 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms.
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).The molecular structure of the two independent cations and anions of the title molecular salt, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. A view of the molecular overlay of the two independent cations (cation A blue, cation B red). A view of the tetramer-like unit enclosing an R84(16) ring motif in the of the title salt. The N–H···Br hydrogen bonds are shown as dashed lines (see Table 1 for details). Crystal packing of the title compound, viewed along the a axis, showing the N–H···Br and C-H···Br hydrogen bonds as dashed lines (see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity). |
C13H15N2+·Br− | Dx = 1.384 Mg m−3 |
Mr = 279.18 | Melting point: 495 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5646 (6) Å | Cell parameters from 5959 reflections |
b = 18.7980 (11) Å | θ = 2.3–24.2° |
c = 26.9782 (16) Å | µ = 3.05 mm−1 |
V = 5357.7 (5) Å3 | T = 294 K |
Z = 16 | Block, yellow |
F(000) = 2272 | 0.13 × 0.11 × 0.09 mm |
Bruker SMART CCD area-detector diffractometer | 6400 independent reflections |
Radiation source: fine focus sealed tube | 4055 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
ω scans | θmax = 28.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −13→13 |
Tmin = 0.66, Tmax = 0.79 | k = −24→24 |
59314 measured reflections | l = −35→35 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: mixed |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0541P)2 + 1.4559P] where P = (Fo2 + 2Fc2)/3 |
6400 reflections | (Δ/σ)max = 0.003 |
307 parameters | Δρmax = 0.66 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C13H15N2+·Br− | V = 5357.7 (5) Å3 |
Mr = 279.18 | Z = 16 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.5646 (6) Å | µ = 3.05 mm−1 |
b = 18.7980 (11) Å | T = 294 K |
c = 26.9782 (16) Å | 0.13 × 0.11 × 0.09 mm |
Bruker SMART CCD area-detector diffractometer | 6400 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 4055 reflections with I > 2σ(I) |
Tmin = 0.66, Tmax = 0.79 | Rint = 0.057 |
59314 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.66 e Å−3 |
6400 reflections | Δρmin = −0.36 e Å−3 |
307 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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.20297 (3) | 0.08005 (2) | 0.52655 (2) | 0.06129 (12) | |
Br2 | 0.49073 (3) | 0.11126 (2) | 0.33059 (2) | 0.07094 (13) | |
N1 | 0.8934 (2) | 0.23701 (13) | 0.47182 (8) | 0.0526 (6) | |
N2 | 0.6590 (3) | 0.07346 (18) | 0.43327 (13) | 0.0690 (8) | |
N3 | −0.0725 (2) | 0.02494 (12) | 0.31892 (8) | 0.0527 (6) | |
N4 | 0.2390 (3) | 0.07293 (16) | 0.40281 (12) | 0.0643 (7) | |
C1 | 0.8056 (3) | 0.24614 (16) | 0.43621 (11) | 0.0545 (7) | |
H1 | 0.7986 | 0.2902 | 0.4208 | 0.065* | |
C2 | 0.7276 (3) | 0.19293 (15) | 0.42224 (10) | 0.0512 (7) | |
H2 | 0.6685 | 0.2005 | 0.3972 | 0.061* | |
C3 | 0.7354 (3) | 0.12630 (15) | 0.44526 (11) | 0.0512 (7) | |
C4 | 0.8294 (3) | 0.11806 (17) | 0.48171 (11) | 0.0579 (7) | |
H4 | 0.8399 | 0.0744 | 0.4974 | 0.069* | |
C5 | 0.9042 (3) | 0.17331 (16) | 0.49393 (11) | 0.0571 (7) | |
H5 | 0.9652 | 0.1672 | 0.5184 | 0.069* | |
C6 | 0.9791 (3) | 0.29613 (17) | 0.48495 (13) | 0.0663 (9) | |
H6A | 1.0192 | 0.2859 | 0.5165 | 0.080* | |
H6B | 0.9301 | 0.3394 | 0.4887 | 0.080* | |
C7 | 1.0797 (3) | 0.30778 (15) | 0.44639 (11) | 0.0564 (7) | |
C8 | 1.0930 (3) | 0.37270 (18) | 0.42366 (14) | 0.0748 (10) | |
H8 | 1.0377 | 0.4095 | 0.4314 | 0.090* | |
C9 | 1.1883 (4) | 0.3837 (2) | 0.38927 (15) | 0.0849 (11) | |
H9 | 1.1959 | 0.4282 | 0.3744 | 0.102* | |
C10 | 1.2714 (3) | 0.3313 (2) | 0.37666 (13) | 0.0753 (10) | |
C11 | 1.2567 (3) | 0.26595 (19) | 0.39924 (14) | 0.0767 (10) | |
H11 | 1.3122 | 0.2292 | 0.3914 | 0.092* | |
C12 | 1.1617 (3) | 0.25412 (17) | 0.43303 (13) | 0.0684 (9) | |
H12 | 1.1527 | 0.2092 | 0.4471 | 0.082* | |
C13 | 1.3778 (5) | 0.3440 (3) | 0.34078 (15) | 0.1151 (16) | |
H13A | 1.4552 | 0.3511 | 0.3588 | 0.173* | |
H13B | 1.3598 | 0.3855 | 0.3213 | 0.173* | |
H13C | 1.3866 | 0.3035 | 0.3194 | 0.173* | |
C14 | −0.0710 (3) | 0.01177 (16) | 0.36826 (10) | 0.0579 (7) | |
H14 | −0.1418 | −0.0089 | 0.3828 | 0.069* | |
C15 | 0.0289 (3) | 0.02757 (16) | 0.39685 (10) | 0.0580 (7) | |
H15 | 0.0259 | 0.0183 | 0.4307 | 0.070* | |
C16 | 0.1381 (3) | 0.05795 (14) | 0.37614 (10) | 0.0503 (7) | |
C17 | 0.1351 (3) | 0.07113 (16) | 0.32494 (10) | 0.0579 (7) | |
H17 | 0.2052 | 0.0911 | 0.3093 | 0.070* | |
C18 | 0.0305 (3) | 0.05486 (16) | 0.29817 (11) | 0.0576 (7) | |
H18 | 0.0298 | 0.0647 | 0.2644 | 0.069* | |
C19 | −0.1864 (3) | 0.00951 (18) | 0.28897 (12) | 0.0677 (9) | |
H19A | −0.1702 | 0.0227 | 0.2548 | 0.081* | |
H19B | −0.2560 | 0.0385 | 0.3009 | 0.081* | |
C20 | −0.2245 (3) | −0.06752 (17) | 0.29092 (11) | 0.0585 (8) | |
C21 | −0.3357 (3) | −0.08812 (19) | 0.31320 (13) | 0.0685 (9) | |
H21 | −0.3878 | −0.0542 | 0.3279 | 0.082* | |
C22 | −0.3705 (4) | −0.1588 (2) | 0.31388 (13) | 0.0787 (10) | |
H22 | −0.4461 | −0.1716 | 0.3291 | 0.094* | |
C23 | −0.2974 (4) | −0.2105 (2) | 0.29295 (15) | 0.0845 (11) | |
C24 | −0.1864 (4) | −0.1896 (2) | 0.27187 (18) | 0.1021 (14) | |
H24 | −0.1337 | −0.2239 | 0.2580 | 0.122* | |
C25 | −0.1498 (4) | −0.1197 (2) | 0.27045 (16) | 0.0883 (12) | |
H25 | −0.0736 | −0.1074 | 0.2555 | 0.106* | |
C26 | −0.3374 (5) | −0.2880 (2) | 0.29280 (19) | 0.1277 (19) | |
H26A | −0.4078 | −0.2944 | 0.3149 | 0.192* | |
H26B | −0.2680 | −0.3171 | 0.3036 | 0.192* | |
H26C | −0.3618 | −0.3017 | 0.2599 | 0.192* | |
H1N2 | 0.613 (3) | 0.0776 (16) | 0.4100 (12) | 0.057 (10)* | |
H1N4 | 0.305 (3) | 0.0899 (17) | 0.3877 (13) | 0.074 (11)* | |
H2N4 | 0.230 (3) | 0.0685 (15) | 0.4322 (13) | 0.055 (9)* | |
H2N2 | 0.674 (3) | 0.0357 (18) | 0.4451 (12) | 0.059 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0765 (2) | 0.05288 (19) | 0.05445 (19) | −0.00899 (15) | −0.00301 (14) | 0.00835 (13) |
Br2 | 0.0549 (2) | 0.1048 (3) | 0.05311 (19) | 0.00089 (17) | −0.00372 (14) | −0.01363 (17) |
N1 | 0.0399 (12) | 0.0587 (15) | 0.0591 (14) | 0.0007 (11) | −0.0039 (10) | −0.0095 (11) |
N2 | 0.0686 (19) | 0.0570 (19) | 0.081 (2) | −0.0046 (15) | −0.0201 (17) | 0.0050 (16) |
N3 | 0.0518 (13) | 0.0577 (14) | 0.0486 (13) | 0.0059 (11) | 0.0006 (11) | 0.0076 (11) |
N4 | 0.073 (2) | 0.0718 (19) | 0.0485 (16) | −0.0098 (15) | 0.0005 (15) | −0.0026 (14) |
C1 | 0.0522 (16) | 0.0535 (17) | 0.0578 (17) | 0.0041 (14) | −0.0007 (13) | −0.0003 (13) |
C2 | 0.0463 (15) | 0.0568 (17) | 0.0506 (15) | 0.0048 (13) | −0.0067 (12) | −0.0039 (13) |
C3 | 0.0441 (15) | 0.0553 (18) | 0.0542 (16) | 0.0020 (13) | −0.0001 (12) | −0.0051 (13) |
C4 | 0.0562 (17) | 0.0577 (19) | 0.0596 (18) | 0.0088 (14) | −0.0068 (14) | 0.0011 (14) |
C5 | 0.0481 (16) | 0.066 (2) | 0.0575 (17) | 0.0103 (15) | −0.0097 (13) | −0.0048 (15) |
C6 | 0.0542 (18) | 0.066 (2) | 0.078 (2) | −0.0051 (15) | −0.0061 (15) | −0.0222 (17) |
C7 | 0.0517 (17) | 0.0467 (17) | 0.0709 (19) | −0.0067 (13) | −0.0070 (14) | −0.0114 (14) |
C8 | 0.072 (2) | 0.0532 (19) | 0.099 (3) | 0.0015 (17) | −0.014 (2) | −0.0066 (18) |
C9 | 0.102 (3) | 0.062 (2) | 0.090 (3) | −0.025 (2) | −0.012 (2) | 0.011 (2) |
C10 | 0.083 (2) | 0.072 (2) | 0.071 (2) | −0.026 (2) | 0.0015 (18) | −0.0113 (18) |
C11 | 0.071 (2) | 0.063 (2) | 0.096 (3) | −0.0114 (18) | 0.0198 (19) | −0.0146 (19) |
C12 | 0.070 (2) | 0.0451 (17) | 0.090 (2) | −0.0081 (15) | 0.0087 (18) | −0.0014 (16) |
C13 | 0.126 (4) | 0.122 (4) | 0.097 (3) | −0.054 (3) | 0.029 (3) | −0.012 (3) |
C14 | 0.0540 (17) | 0.0681 (19) | 0.0515 (16) | 0.0025 (15) | 0.0119 (14) | 0.0086 (14) |
C15 | 0.070 (2) | 0.0645 (19) | 0.0397 (14) | 0.0002 (15) | 0.0102 (14) | 0.0036 (13) |
C16 | 0.0550 (17) | 0.0477 (16) | 0.0481 (16) | 0.0051 (13) | 0.0061 (13) | −0.0061 (12) |
C17 | 0.0582 (18) | 0.067 (2) | 0.0490 (16) | −0.0052 (15) | 0.0103 (14) | 0.0033 (14) |
C18 | 0.0652 (19) | 0.0655 (19) | 0.0422 (15) | 0.0035 (15) | 0.0077 (13) | 0.0094 (13) |
C19 | 0.0534 (17) | 0.083 (2) | 0.0666 (19) | 0.0043 (16) | −0.0105 (15) | 0.0140 (17) |
C20 | 0.0488 (17) | 0.072 (2) | 0.0544 (17) | 0.0084 (14) | −0.0113 (13) | −0.0025 (14) |
C21 | 0.067 (2) | 0.074 (2) | 0.065 (2) | 0.0093 (17) | 0.0011 (16) | −0.0046 (17) |
C22 | 0.085 (2) | 0.080 (3) | 0.071 (2) | −0.011 (2) | −0.0082 (19) | 0.0051 (19) |
C23 | 0.098 (3) | 0.072 (2) | 0.084 (3) | 0.006 (2) | −0.045 (2) | −0.005 (2) |
C24 | 0.087 (3) | 0.085 (3) | 0.134 (4) | 0.029 (2) | −0.019 (3) | −0.043 (3) |
C25 | 0.059 (2) | 0.103 (3) | 0.102 (3) | 0.010 (2) | 0.001 (2) | −0.028 (2) |
C26 | 0.166 (5) | 0.074 (3) | 0.143 (4) | −0.007 (3) | −0.074 (4) | −0.017 (3) |
N1—C5 | 1.343 (4) | C11—C12 | 1.374 (4) |
N1—C1 | 1.346 (3) | C11—H11 | 0.9300 |
N1—C6 | 1.477 (4) | C12—H12 | 0.9300 |
N2—C3 | 1.320 (4) | C13—H13A | 0.9600 |
N2—H1N2 | 0.80 (3) | C13—H13B | 0.9600 |
N2—H2N2 | 0.79 (3) | C13—H13C | 0.9600 |
N3—C18 | 1.347 (4) | C14—C15 | 1.341 (4) |
N3—C14 | 1.354 (3) | C14—H14 | 0.9300 |
N3—C19 | 1.478 (4) | C15—C16 | 1.403 (4) |
N4—C16 | 1.316 (4) | C15—H15 | 0.9300 |
N4—H1N4 | 0.87 (3) | C16—C17 | 1.404 (4) |
N4—H2N4 | 0.80 (3) | C17—C18 | 1.355 (4) |
C1—C2 | 1.350 (4) | C17—H17 | 0.9300 |
C1—H1 | 0.9300 | C18—H18 | 0.9300 |
C2—C3 | 1.400 (4) | C19—C20 | 1.504 (4) |
C2—H2 | 0.9300 | C19—H19A | 0.9700 |
C3—C4 | 1.406 (4) | C19—H19B | 0.9700 |
C4—C5 | 1.346 (4) | C20—C21 | 1.375 (5) |
C4—H4 | 0.9300 | C20—C25 | 1.375 (5) |
C5—H5 | 0.9300 | C21—C22 | 1.378 (5) |
C6—C7 | 1.503 (4) | C21—H21 | 0.9300 |
C6—H6A | 0.9700 | C22—C23 | 1.363 (5) |
C6—H6B | 0.9700 | C22—H22 | 0.9300 |
C7—C8 | 1.373 (4) | C23—C24 | 1.361 (6) |
C7—C12 | 1.378 (4) | C23—C26 | 1.519 (6) |
C8—C9 | 1.385 (5) | C24—C25 | 1.370 (6) |
C8—H8 | 0.9300 | C24—H24 | 0.9300 |
C9—C10 | 1.363 (5) | C25—H25 | 0.9300 |
C9—H9 | 0.9300 | C26—H26A | 0.9600 |
C10—C11 | 1.380 (5) | C26—H26B | 0.9600 |
C10—C13 | 1.503 (5) | C26—H26C | 0.9600 |
C5—N1—C1 | 119.3 (2) | C10—C13—H13A | 109.5 |
C5—N1—C6 | 120.8 (2) | C10—C13—H13B | 109.5 |
C1—N1—C6 | 119.8 (3) | H13A—C13—H13B | 109.5 |
C3—N2—H1N2 | 119 (2) | C10—C13—H13C | 109.5 |
C3—N2—H2N2 | 117 (2) | H13A—C13—H13C | 109.5 |
H1N2—N2—H2N2 | 122 (3) | H13B—C13—H13C | 109.5 |
C18—N3—C14 | 118.4 (2) | C15—C14—N3 | 122.3 (3) |
C18—N3—C19 | 120.8 (2) | C15—C14—H14 | 118.9 |
C14—N3—C19 | 120.7 (2) | N3—C14—H14 | 118.9 |
C16—N4—H1N4 | 118 (2) | C14—C15—C16 | 120.6 (3) |
C16—N4—H2N4 | 115 (2) | C14—C15—H15 | 119.7 |
H1N4—N4—H2N4 | 127 (3) | C16—C15—H15 | 119.7 |
N1—C1—C2 | 121.7 (3) | N4—C16—C15 | 122.4 (3) |
N1—C1—H1 | 119.2 | N4—C16—C17 | 121.2 (3) |
C2—C1—H1 | 119.2 | C15—C16—C17 | 116.4 (3) |
C1—C2—C3 | 120.2 (3) | C18—C17—C16 | 120.2 (3) |
C1—C2—H2 | 119.9 | C18—C17—H17 | 119.9 |
C3—C2—H2 | 119.9 | C16—C17—H17 | 119.9 |
N2—C3—C2 | 121.9 (3) | N3—C18—C17 | 122.1 (3) |
N2—C3—C4 | 121.4 (3) | N3—C18—H18 | 118.9 |
C2—C3—C4 | 116.8 (3) | C17—C18—H18 | 118.9 |
C5—C4—C3 | 120.1 (3) | N3—C19—C20 | 112.8 (2) |
C5—C4—H4 | 120.0 | N3—C19—H19A | 109.0 |
C3—C4—H4 | 120.0 | C20—C19—H19A | 109.0 |
N1—C5—C4 | 122.0 (3) | N3—C19—H19B | 109.0 |
N1—C5—H5 | 119.0 | C20—C19—H19B | 109.0 |
C4—C5—H5 | 119.0 | H19A—C19—H19B | 107.8 |
N1—C6—C7 | 112.2 (2) | C21—C20—C25 | 117.7 (3) |
N1—C6—H6A | 109.2 | C21—C20—C19 | 121.0 (3) |
C7—C6—H6A | 109.2 | C25—C20—C19 | 121.3 (3) |
N1—C6—H6B | 109.2 | C20—C21—C22 | 120.3 (3) |
C7—C6—H6B | 109.2 | C20—C21—H21 | 119.8 |
H6A—C6—H6B | 107.9 | C22—C21—H21 | 119.8 |
C8—C7—C12 | 118.0 (3) | C23—C22—C21 | 122.0 (4) |
C8—C7—C6 | 120.7 (3) | C23—C22—H22 | 119.0 |
C12—C7—C6 | 121.3 (3) | C21—C22—H22 | 119.0 |
C7—C8—C9 | 120.5 (3) | C24—C23—C22 | 117.1 (4) |
C7—C8—H8 | 119.8 | C24—C23—C26 | 121.1 (4) |
C9—C8—H8 | 119.8 | C22—C23—C26 | 121.8 (4) |
C10—C9—C8 | 121.8 (3) | C23—C24—C25 | 122.1 (4) |
C10—C9—H9 | 119.1 | C23—C24—H24 | 119.0 |
C8—C9—H9 | 119.1 | C25—C24—H24 | 119.0 |
C9—C10—C11 | 117.5 (3) | C24—C25—C20 | 120.7 (4) |
C9—C10—C13 | 121.8 (4) | C24—C25—H25 | 119.6 |
C11—C10—C13 | 120.7 (4) | C20—C25—H25 | 119.6 |
C12—C11—C10 | 121.3 (3) | C23—C26—H26A | 109.5 |
C12—C11—H11 | 119.4 | C23—C26—H26B | 109.5 |
C10—C11—H11 | 119.4 | H26A—C26—H26B | 109.5 |
C11—C12—C7 | 121.0 (3) | C23—C26—H26C | 109.5 |
C11—C12—H12 | 119.5 | H26A—C26—H26C | 109.5 |
C7—C12—H12 | 119.5 | H26B—C26—H26C | 109.5 |
C5—N1—C1—C2 | 0.3 (4) | C18—N3—C14—C15 | 0.1 (4) |
C6—N1—C1—C2 | 178.3 (3) | C19—N3—C14—C15 | −177.5 (3) |
N1—C1—C2—C3 | 0.8 (4) | N3—C14—C15—C16 | −0.9 (5) |
C1—C2—C3—N2 | 178.6 (3) | C14—C15—C16—N4 | −178.7 (3) |
C1—C2—C3—C4 | −1.8 (4) | C14—C15—C16—C17 | 0.7 (4) |
N2—C3—C4—C5 | −178.6 (3) | N4—C16—C17—C18 | 179.6 (3) |
C2—C3—C4—C5 | 1.8 (4) | C15—C16—C17—C18 | 0.2 (4) |
C1—N1—C5—C4 | −0.3 (4) | C14—N3—C18—C17 | 0.9 (4) |
C6—N1—C5—C4 | −178.2 (3) | C19—N3—C18—C17 | 178.4 (3) |
C3—C4—C5—N1 | −0.8 (5) | C16—C17—C18—N3 | −1.0 (5) |
C5—N1—C6—C7 | 103.4 (3) | C18—N3—C19—C20 | 123.3 (3) |
C1—N1—C6—C7 | −74.6 (3) | C14—N3—C19—C20 | −59.2 (4) |
N1—C6—C7—C8 | 122.9 (3) | N3—C19—C20—C21 | 113.3 (3) |
N1—C6—C7—C12 | −57.6 (4) | N3—C19—C20—C25 | −66.9 (4) |
C12—C7—C8—C9 | −1.5 (5) | C25—C20—C21—C22 | −1.1 (5) |
C6—C7—C8—C9 | 178.0 (3) | C19—C20—C21—C22 | 178.8 (3) |
C7—C8—C9—C10 | 0.2 (6) | C20—C21—C22—C23 | 0.1 (5) |
C8—C9—C10—C11 | 0.4 (6) | C21—C22—C23—C24 | 1.2 (5) |
C8—C9—C10—C13 | −177.7 (4) | C21—C22—C23—C26 | −178.6 (3) |
C9—C10—C11—C12 | 0.2 (5) | C22—C23—C24—C25 | −1.5 (6) |
C13—C10—C11—C12 | 178.4 (4) | C26—C23—C24—C25 | 178.3 (4) |
C10—C11—C12—C7 | −1.6 (5) | C23—C24—C25—C20 | 0.5 (7) |
C8—C7—C12—C11 | 2.2 (5) | C21—C20—C25—C24 | 0.8 (6) |
C6—C7—C12—C11 | −177.3 (3) | C19—C20—C25—C24 | −179.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···Br2 | 0.80 (3) | 2.58 (3) | 3.367 (4) | 169 (3) |
N4—H1N4···Br2 | 0.87 (3) | 2.52 (4) | 3.375 (3) | 166 (3) |
N4—H2N4···Br1 | 0.80 (3) | 2.57 (3) | 3.363 (3) | 169 (3) |
N2—H2N2···Br1i | 0.79 (3) | 2.65 (3) | 3.410 (4) | 161 (3) |
C6—H6B···Br1ii | 0.97 | 2.87 | 3.745 (3) | 151 |
C14—H14···Br1iii | 0.93 | 2.86 | 3.602 (3) | 138 |
C18—H18···Br2iv | 0.93 | 2.74 | 3.656 (3) | 169 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1/2, −y+1/2, −z+1; (iii) −x, −y, −z+1; (iv) x−1/2, y, −z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···Br2 | 0.80 (3) | 2.58 (3) | 3.367 (4) | 169 (3) |
N4—H1N4···Br2 | 0.87 (3) | 2.52 (4) | 3.375 (3) | 166 (3) |
N4—H2N4···Br1 | 0.80 (3) | 2.57 (3) | 3.363 (3) | 169 (3) |
N2—H2N2···Br1i | 0.79 (3) | 2.65 (3) | 3.410 (4) | 161 (3) |
C6—H6B···Br1ii | 0.97 | 2.87 | 3.745 (3) | 151 |
C14—H14···Br1iii | 0.93 | 2.86 | 3.602 (3) | 138 |
C18—H18···Br2iv | 0.93 | 2.74 | 3.656 (3) | 169 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1/2, −y+1/2, −z+1; (iii) −x, −y, −z+1; (iv) x−1/2, y, −z−1/2. |
Acknowledgements
NS thanks Dr K. Ravikumar of the Indian Institute of Chemical Technology, Hyderabad, for his kind help and useful discussions.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Quarternary amine derivatives have been reported to possess antimicrobial properties (Thorsteinsson et al., 2003). The use of 4-aminopyridine derivatives are reported to be useful for the treatment of a peripheral nervous system demyelinating disease selected from Guillain-Barre syndrome diabetes mellitus and hereditary sensory-motor neuropathy. Literature information revealed that the use of 4-aminopyridine had reduced chronic pain and spasticity in spinal cord injured patients (Hansebout et al., 1996). The crystal structures of a large number of pyridinium derivatives have been reported (Seethalakshmi et al., 2006; Sundar et al., 2006a,b,c) and their antimicrobial activities have also been reported (Ilangovan et al., 2012; Sundararaman et al., 2013).
The molecular structure of the two independent cations and anions of the title molecular salt is illustrated in Fig. 1. In the cations, the pyridine and benzene rings are inclined to one another by 79.32 (8)° in molecule A and by 82.30 (10)° in molecule B (Fig. 2). These values are similar to those observed in the crystal structures of some related compounds (Seethalakshmi et al., 2006; Sundar et al., 2006a,b,c). The overlap of the two cations in the title compound is illustrated in Fig. 2.
In the crystal, the cations and anions are linked via N-H···Br hydrogen bonds forming a tetramer-like unit enclosing an R84(16) ring motif (Table 1 and Fig. 3). These units are linked via C-H···Br hydrogen bonds forming a three-dimensional framework (Table 1 and Fig. 4).