organic compounds
2-[(E)-4-(Dimethylamino)styryl]-1-methylpyridinium 4-chlorobenzenesulfonate monohydrate1
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
*Correspondence e-mail: hkfun@usm.my
In the title hydrated molecular salt, C16H19N2+·C6H4ClO3S−·H2O, the 2-[4-(dimethylamino)styryl]-1-methylpyridinium cation exists in an E configuration with respect to the C=C bond and is slightly twisted, with the dihedral angle between the pyridinium and benzene rings being 9.33 (10)°. In the the packing is stabilized by O—H⋯O hydrogen bonds and weak C—H⋯O interactions, which link the cations, anions and water molecules into chains propagating in [010]. These chains are stacked along the a axis by π–π interactions, with centroid-to-centroid distances of 3.6429 (12) and 3.6879 (12) Å; weak C—H⋯π interactions are also observed.
Related literature
For representative bond lengths, see Allen et al. (1987). For background to and application of quarternary see: Armitage et al. (1929); Browning et al. (1922); Chanawanno et al. (2010); Wainwright & Kristiansen (2003); Wainwright (2008). For a related structure, see: Chantrapromma et al. (2010). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536810043230/hb5695sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043230/hb5695Isup2.hkl
The title compound was prepared by the reported procedure (Chanawanno et al., 2010). Orange blocks of (I) were recrystallized from methanol by slow evaporation of the solvent at room temperature after a few weeks, m.p. 516–517 K.
Water H atoms were located in difference maps and refined isotropically. The remaining H atoms were placed in calculated positions with d(C—H) = 0.93 Å, Uiso = 1.2Ueq(C) for aromatic and CH and 0.96 Å, Uiso = 1.5Ueq(C) for CH3 atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 0.69 Å from C11 and the deepest hole is located at 0.67 Å from S1.
Our research group have designed and synthesized some
including pyridinium derivatives. However, there are very few researches in the area of styryl pyridinium dyes being used as antibacterial agents. Based on the knowledge gathered since a very long time ago (Armitage et al., 1929; Browning et al., 1922; Wainwright & Kristiansen, 2003), we found that styryl pyridinium compounds possess high activity against both susceptible and methicillin-resistant Staphylococcus aureus (MRSA) (Chanawanno et al., 2010). This interesting anti-MRSA activity of the styryl pyridinium compounds trigger an encouragement to perform further investigation of these compounds in order to act against the powerful superbug MRSA which can overcome commonly used antibacterial drugs (Wainwright, 2008). Our bacterial assay results show that the title compound was moderately active against MRSA with the minimum inhibition concentration (MIC) = 37.5 µg/ml. Herein its is reported.Fig. 1 shows the ═C7 double bond [1.349 (3) Å]. The cation is slightly twisted with the dihedral angle between the C1–C5/N1 pyridinium and the C8–C13 benzene rings being 9.33 (10)° and with the torsion angles C5—C6—C7—C8 = -178.7 (2)°. The two methyl groups of dimethylamino moiety are slightly twisted from the mean plane of the attached C8–C13 ring as indicated by the torsion angles C15—N2—C11—C10 = -2.5 (3)° and C16—N2—C11—C12 = -9.1 (3)°. The cation and anion are inclined to each other which indicated by the dihedral angles between the C17–C22 benzene ring of anion and pyridinium and C8–C13 benzene rings of cation being 79.19 (10) and 70.20 (10)°, respectively. The bond lengths (Allen et al., 1987) and angles in (I) are in normal ranges and comparable with a related structure (Chantrapromma et al., 2010).
of the title compound (I) which consists of the C16H19N2+ cation, C6H4ClO3S- anion and one H2O molecule. The cation exists in the E configuration with respect to the C6In the crystal packing, all O atoms of the sulfonate group are involved in weak C—H···O interactions (Table 1). The cation is linked to both the anion and water molecule by weak C—H···O interactions, and the anion is linked to the water molecule by O—H···O hydrogen bond. These three molecules are linked into chains along the b axis (Table 1, Fig. 2). These chains are stacked along the the a axis (Fig. 2) by π–π interactions with the distances Cg1···Cg1 = 3.6429 (12) Å (symmetry code: -x, -y, -z) and Cg1···Cg2 = 3.6879 (12) Å (symmetry code: -1 + x, y, z). C—H···π interactions were also observed (Table 1); Cg1, Cg2 and Cg3 are the centroids of the C1–C5/N1, C8–C13 and C17–C22 rings, respectively.
For bond lengths and angles, see Allen et al. (1987). For background to and application of quarternary
see: Armitage et al. (1929); Browning et al. (1922); Chanawanno et al. (2010); Wainwright & Kristiansen (2003); Wainwright (2008). For a related structure, see: Chantrapromma et al. (2010). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The asymmetric unit of (I) showing 50% probability displacement ellipsoids. | |
Fig. 2. The crystal packing of (I) viewed along the a axis. The O—H···O hydrogen bonds and weak C—H···O interactions are drawn as dashed lines. |
C16H19N2+·C6H4ClO3S−·H2O | Z = 2 |
Mr = 448.96 | F(000) = 472 |
Triclinic, P1 | Dx = 1.397 Mg m−3 |
Hall symbol: -P 1 | Melting point = 516–517 K |
a = 6.3895 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.8739 (2) Å | Cell parameters from 6156 reflections |
c = 17.0074 (3) Å | θ = 1.2–30.0° |
α = 95.721 (1)° | µ = 0.31 mm−1 |
β = 90.500 (1)° | T = 100 K |
γ = 91.260 (1)° | Block, orange |
V = 1067.32 (3) Å3 | 0.31 × 0.10 × 0.05 mm |
Bruker APEX DUO CCD diffractometer | 6156 independent reflections |
Radiation source: sealed tube | 4327 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.065 |
φ and ω scans | θmax = 30.0°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −8→8 |
Tmin = 0.912, Tmax = 0.984 | k = −12→13 |
23113 measured reflections | l = −23→23 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0548P)2 + 0.637P] where P = (Fo2 + 2Fc2)/3 |
6156 reflections | (Δ/σ)max = 0.001 |
282 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
C16H19N2+·C6H4ClO3S−·H2O | γ = 91.260 (1)° |
Mr = 448.96 | V = 1067.32 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.3895 (1) Å | Mo Kα radiation |
b = 9.8739 (2) Å | µ = 0.31 mm−1 |
c = 17.0074 (3) Å | T = 100 K |
α = 95.721 (1)° | 0.31 × 0.10 × 0.05 mm |
β = 90.500 (1)° |
Bruker APEX DUO CCD diffractometer | 6156 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4327 reflections with I > 2σ(I) |
Tmin = 0.912, Tmax = 0.984 | Rint = 0.065 |
23113 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.47 e Å−3 |
6156 reflections | Δρmin = −0.43 e Å−3 |
282 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
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 | ||
N1 | 0.0246 (3) | 0.11936 (19) | 0.10897 (11) | 0.0156 (4) | |
N2 | 1.2149 (3) | 0.17645 (19) | 0.39494 (11) | 0.0193 (4) | |
C1 | −0.1576 (3) | 0.0753 (2) | 0.07232 (13) | 0.0173 (4) | |
H1A | −0.2417 | 0.1374 | 0.0500 | 0.021* | |
C2 | −0.2199 (3) | −0.0591 (2) | 0.06768 (13) | 0.0188 (5) | |
H2A | −0.3458 | −0.0881 | 0.0431 | 0.023* | |
C3 | −0.0922 (3) | −0.1511 (2) | 0.10026 (13) | 0.0189 (5) | |
H3A | −0.1307 | −0.2429 | 0.0969 | 0.023* | |
C4 | 0.0920 (3) | −0.1056 (2) | 0.13766 (13) | 0.0174 (4) | |
H4A | 0.1774 | −0.1676 | 0.1594 | 0.021* | |
C5 | 0.1533 (3) | 0.0327 (2) | 0.14361 (12) | 0.0157 (4) | |
C6 | 0.3439 (3) | 0.0866 (2) | 0.18323 (13) | 0.0167 (4) | |
H6A | 0.3830 | 0.1767 | 0.1785 | 0.020* | |
C7 | 0.4671 (3) | 0.0127 (2) | 0.22659 (13) | 0.0167 (4) | |
H7A | 0.4256 | −0.0776 | 0.2294 | 0.020* | |
C8 | 0.6572 (3) | 0.0584 (2) | 0.26937 (13) | 0.0162 (4) | |
C9 | 0.7629 (3) | −0.0320 (2) | 0.31341 (13) | 0.0173 (4) | |
H9A | 0.7088 | −0.1201 | 0.3143 | 0.021* | |
C10 | 0.9449 (3) | 0.0052 (2) | 0.35563 (13) | 0.0181 (4) | |
H10A | 1.0101 | −0.0573 | 0.3845 | 0.022* | |
C11 | 1.0323 (3) | 0.1382 (2) | 0.35494 (13) | 0.0161 (4) | |
C12 | 0.9253 (3) | 0.2302 (2) | 0.31130 (13) | 0.0168 (4) | |
H12A | 0.9784 | 0.3185 | 0.3103 | 0.020* | |
C13 | 0.7425 (3) | 0.1910 (2) | 0.26998 (13) | 0.0162 (4) | |
H13A | 0.6747 | 0.2537 | 0.2420 | 0.019* | |
C14 | 0.0814 (4) | 0.2658 (2) | 0.10930 (14) | 0.0198 (5) | |
H14A | 0.1017 | 0.3053 | 0.1628 | 0.030* | |
H14B | −0.0291 | 0.3115 | 0.0849 | 0.030* | |
H14C | 0.2084 | 0.2754 | 0.0804 | 0.030* | |
C15 | 1.3197 (4) | 0.0833 (3) | 0.44178 (15) | 0.0237 (5) | |
H15A | 1.2260 | 0.0554 | 0.4813 | 0.036* | |
H15B | 1.4412 | 0.1278 | 0.4670 | 0.036* | |
H15C | 1.3614 | 0.0048 | 0.4082 | 0.036* | |
C16 | 1.3169 (3) | 0.3058 (2) | 0.38333 (14) | 0.0204 (5) | |
H16A | 1.3290 | 0.3140 | 0.3278 | 0.031* | |
H16B | 1.4538 | 0.3098 | 0.4072 | 0.031* | |
H16C | 1.2352 | 0.3789 | 0.4073 | 0.031* | |
Cl1 | 1.18810 (10) | 0.69360 (7) | 0.46691 (4) | 0.02879 (16) | |
S1 | 0.57475 (8) | 0.54114 (6) | 0.17948 (3) | 0.01647 (13) | |
O1 | 0.4692 (2) | 0.66863 (16) | 0.17231 (10) | 0.0204 (3) | |
O2 | 0.4357 (3) | 0.43430 (17) | 0.20239 (10) | 0.0249 (4) | |
O3 | 0.7023 (3) | 0.50131 (18) | 0.11086 (10) | 0.0247 (4) | |
C17 | 0.7541 (3) | 0.5767 (2) | 0.26013 (13) | 0.0164 (4) | |
C18 | 0.6803 (3) | 0.5782 (2) | 0.33656 (13) | 0.0192 (5) | |
H18A | 0.5409 | 0.5554 | 0.3451 | 0.023* | |
C19 | 0.8147 (4) | 0.6137 (2) | 0.40055 (14) | 0.0209 (5) | |
H19A | 0.7663 | 0.6153 | 0.4520 | 0.025* | |
C20 | 1.0214 (3) | 0.6468 (2) | 0.38611 (13) | 0.0190 (5) | |
C21 | 1.0976 (3) | 0.6445 (2) | 0.31068 (14) | 0.0204 (5) | |
H21A | 1.2371 | 0.6672 | 0.3024 | 0.024* | |
C22 | 0.9634 (3) | 0.6076 (2) | 0.24660 (14) | 0.0184 (4) | |
H22A | 1.0134 | 0.6037 | 0.1953 | 0.022* | |
O1W | 0.5623 (3) | 0.29024 (19) | 0.99640 (12) | 0.0270 (4) | |
H1W1 | 0.595 (5) | 0.366 (4) | 1.026 (2) | 0.054 (10)* | |
H2W1 | 0.552 (6) | 0.317 (4) | 0.946 (3) | 0.075 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0147 (8) | 0.0158 (9) | 0.0156 (9) | −0.0006 (7) | −0.0013 (7) | −0.0013 (7) |
N2 | 0.0156 (9) | 0.0188 (10) | 0.0236 (10) | −0.0026 (7) | −0.0070 (7) | 0.0046 (8) |
C1 | 0.0133 (9) | 0.0227 (11) | 0.0157 (10) | 0.0012 (8) | −0.0015 (8) | 0.0004 (9) |
C2 | 0.0155 (10) | 0.0239 (12) | 0.0164 (11) | −0.0026 (9) | −0.0017 (8) | −0.0008 (9) |
C3 | 0.0196 (10) | 0.0178 (11) | 0.0188 (11) | −0.0048 (9) | −0.0009 (8) | 0.0002 (9) |
C4 | 0.0171 (10) | 0.0168 (11) | 0.0183 (11) | 0.0001 (8) | −0.0018 (8) | 0.0018 (8) |
C5 | 0.0132 (9) | 0.0197 (11) | 0.0139 (10) | 0.0018 (8) | −0.0010 (8) | −0.0002 (8) |
C6 | 0.0150 (10) | 0.0157 (10) | 0.0189 (11) | −0.0024 (8) | −0.0010 (8) | 0.0004 (8) |
C7 | 0.0157 (10) | 0.0138 (10) | 0.0198 (11) | −0.0014 (8) | −0.0010 (8) | −0.0014 (8) |
C8 | 0.0146 (10) | 0.0174 (11) | 0.0161 (10) | 0.0016 (8) | −0.0005 (8) | −0.0006 (8) |
C9 | 0.0181 (10) | 0.0134 (10) | 0.0200 (11) | −0.0015 (8) | −0.0005 (8) | 0.0000 (8) |
C10 | 0.0200 (10) | 0.0162 (11) | 0.0185 (11) | 0.0022 (8) | −0.0028 (8) | 0.0040 (8) |
C11 | 0.0137 (9) | 0.0202 (11) | 0.0139 (10) | −0.0008 (8) | −0.0008 (8) | −0.0010 (8) |
C12 | 0.0164 (10) | 0.0167 (11) | 0.0171 (10) | −0.0023 (8) | −0.0007 (8) | 0.0012 (8) |
C13 | 0.0162 (10) | 0.0173 (11) | 0.0153 (10) | 0.0013 (8) | −0.0004 (8) | 0.0025 (8) |
C14 | 0.0194 (10) | 0.0152 (11) | 0.0249 (12) | −0.0007 (8) | −0.0031 (9) | 0.0024 (9) |
C15 | 0.0183 (11) | 0.0275 (13) | 0.0260 (12) | −0.0007 (9) | −0.0068 (9) | 0.0073 (10) |
C16 | 0.0182 (10) | 0.0220 (11) | 0.0205 (11) | −0.0047 (9) | −0.0029 (8) | 0.0005 (9) |
Cl1 | 0.0305 (3) | 0.0304 (3) | 0.0238 (3) | −0.0009 (3) | −0.0125 (2) | −0.0040 (2) |
S1 | 0.0171 (3) | 0.0136 (3) | 0.0182 (3) | −0.00053 (19) | −0.0044 (2) | −0.0003 (2) |
O1 | 0.0215 (8) | 0.0158 (8) | 0.0239 (9) | 0.0022 (6) | −0.0041 (6) | 0.0017 (6) |
O2 | 0.0251 (8) | 0.0192 (8) | 0.0306 (10) | −0.0073 (7) | −0.0091 (7) | 0.0056 (7) |
O3 | 0.0225 (8) | 0.0312 (10) | 0.0187 (8) | 0.0052 (7) | −0.0026 (6) | −0.0070 (7) |
C17 | 0.0186 (10) | 0.0104 (10) | 0.0199 (11) | 0.0008 (8) | −0.0036 (8) | 0.0004 (8) |
C18 | 0.0173 (10) | 0.0202 (11) | 0.0202 (11) | −0.0008 (9) | 0.0001 (8) | 0.0023 (9) |
C19 | 0.0257 (11) | 0.0207 (11) | 0.0159 (11) | 0.0005 (9) | 0.0002 (9) | 0.0001 (9) |
C20 | 0.0212 (11) | 0.0161 (11) | 0.0191 (11) | 0.0019 (9) | −0.0061 (9) | −0.0014 (9) |
C21 | 0.0159 (10) | 0.0183 (11) | 0.0266 (12) | −0.0019 (9) | −0.0048 (9) | 0.0013 (9) |
C22 | 0.0207 (11) | 0.0166 (11) | 0.0180 (11) | 0.0011 (9) | −0.0005 (8) | 0.0013 (9) |
O1W | 0.0358 (10) | 0.0209 (9) | 0.0238 (10) | −0.0001 (8) | −0.0092 (8) | 0.0010 (8) |
N1—C1 | 1.358 (3) | C13—H13A | 0.9300 |
N1—C5 | 1.371 (3) | C14—H14A | 0.9600 |
N1—C14 | 1.482 (3) | C14—H14B | 0.9600 |
N2—C11 | 1.372 (2) | C14—H14C | 0.9600 |
N2—C15 | 1.447 (3) | C15—H15A | 0.9600 |
N2—C16 | 1.452 (3) | C15—H15B | 0.9600 |
C1—C2 | 1.372 (3) | C15—H15C | 0.9600 |
C1—H1A | 0.9300 | C16—H16A | 0.9600 |
C2—C3 | 1.387 (3) | C16—H16B | 0.9600 |
C2—H2A | 0.9300 | C16—H16C | 0.9600 |
C3—C4 | 1.378 (3) | Cl1—C20 | 1.750 (2) |
C3—H3A | 0.9300 | S1—O2 | 1.4495 (17) |
C4—C5 | 1.406 (3) | S1—O3 | 1.4562 (18) |
C4—H4A | 0.9300 | S1—O1 | 1.4561 (16) |
C5—C6 | 1.451 (3) | S1—C17 | 1.782 (2) |
C6—C7 | 1.349 (3) | C17—C18 | 1.386 (3) |
C6—H6A | 0.9300 | C17—C22 | 1.391 (3) |
C7—C8 | 1.451 (3) | C18—C19 | 1.392 (3) |
C7—H7A | 0.9300 | C18—H18A | 0.9300 |
C8—C9 | 1.402 (3) | C19—C20 | 1.383 (3) |
C8—C13 | 1.406 (3) | C19—H19A | 0.9300 |
C9—C10 | 1.385 (3) | C20—C21 | 1.374 (3) |
C9—H9A | 0.9300 | C21—C22 | 1.395 (3) |
C10—C11 | 1.417 (3) | C21—H21A | 0.9300 |
C10—H10A | 0.9300 | C22—H22A | 0.9300 |
C11—C12 | 1.413 (3) | O1W—H1W1 | 0.88 (4) |
C12—C13 | 1.386 (3) | O1W—H2W1 | 0.91 (4) |
C12—H12A | 0.9300 | ||
C1—N1—C5 | 121.90 (19) | C8—C13—H13A | 119.2 |
C1—N1—C14 | 117.25 (18) | N1—C14—H14A | 109.5 |
C5—N1—C14 | 120.85 (17) | N1—C14—H14B | 109.5 |
C11—N2—C15 | 120.73 (19) | H14A—C14—H14B | 109.5 |
C11—N2—C16 | 119.76 (18) | N1—C14—H14C | 109.5 |
C15—N2—C16 | 119.16 (17) | H14A—C14—H14C | 109.5 |
N1—C1—C2 | 121.1 (2) | H14B—C14—H14C | 109.5 |
N1—C1—H1A | 119.4 | N2—C15—H15A | 109.5 |
C2—C1—H1A | 119.4 | N2—C15—H15B | 109.5 |
C1—C2—C3 | 118.99 (19) | H15A—C15—H15B | 109.5 |
C1—C2—H2A | 120.5 | N2—C15—H15C | 109.5 |
C3—C2—H2A | 120.5 | H15A—C15—H15C | 109.5 |
C4—C3—C2 | 119.6 (2) | H15B—C15—H15C | 109.5 |
C4—C3—H3A | 120.2 | N2—C16—H16A | 109.5 |
C2—C3—H3A | 120.2 | N2—C16—H16B | 109.5 |
C3—C4—C5 | 121.2 (2) | H16A—C16—H16B | 109.5 |
C3—C4—H4A | 119.4 | N2—C16—H16C | 109.5 |
C5—C4—H4A | 119.4 | H16A—C16—H16C | 109.5 |
N1—C5—C4 | 117.15 (18) | H16B—C16—H16C | 109.5 |
N1—C5—C6 | 119.21 (19) | O2—S1—O3 | 114.41 (11) |
C4—C5—C6 | 123.64 (19) | O2—S1—O1 | 113.10 (10) |
C7—C6—C5 | 123.3 (2) | O3—S1—O1 | 112.03 (10) |
C7—C6—H6A | 118.3 | O2—S1—C17 | 105.34 (10) |
C5—C6—H6A | 118.3 | O3—S1—C17 | 105.74 (10) |
C6—C7—C8 | 127.2 (2) | O1—S1—C17 | 105.26 (10) |
C6—C7—H7A | 116.4 | C18—C17—C22 | 120.5 (2) |
C8—C7—H7A | 116.4 | C18—C17—S1 | 118.96 (16) |
C9—C8—C13 | 117.25 (18) | C22—C17—S1 | 120.51 (18) |
C9—C8—C7 | 119.4 (2) | C17—C18—C19 | 120.0 (2) |
C13—C8—C7 | 123.38 (19) | C17—C18—H18A | 120.0 |
C10—C9—C8 | 122.3 (2) | C19—C18—H18A | 120.0 |
C10—C9—H9A | 118.9 | C20—C19—C18 | 118.8 (2) |
C8—C9—H9A | 118.9 | C20—C19—H19A | 120.6 |
C9—C10—C11 | 120.26 (19) | C18—C19—H19A | 120.6 |
C9—C10—H10A | 119.9 | C21—C20—C19 | 121.9 (2) |
C11—C10—H10A | 119.9 | C21—C20—Cl1 | 119.68 (17) |
N2—C11—C12 | 121.0 (2) | C19—C20—Cl1 | 118.42 (18) |
N2—C11—C10 | 121.27 (19) | C20—C21—C22 | 119.3 (2) |
C12—C11—C10 | 117.72 (18) | C20—C21—H21A | 120.4 |
C13—C12—C11 | 121.0 (2) | C22—C21—H21A | 120.4 |
C13—C12—H12A | 119.5 | C17—C22—C21 | 119.5 (2) |
C11—C12—H12A | 119.5 | C17—C22—H22A | 120.3 |
C12—C13—C8 | 121.5 (2) | C21—C22—H22A | 120.3 |
C12—C13—H13A | 119.2 | H1W1—O1W—H2W1 | 104 (3) |
C5—N1—C1—C2 | −0.7 (3) | C9—C10—C11—N2 | −178.6 (2) |
C14—N1—C1—C2 | 178.5 (2) | C9—C10—C11—C12 | 1.1 (3) |
N1—C1—C2—C3 | −0.8 (3) | N2—C11—C12—C13 | 179.1 (2) |
C1—C2—C3—C4 | 1.1 (3) | C10—C11—C12—C13 | −0.7 (3) |
C2—C3—C4—C5 | 0.1 (3) | C11—C12—C13—C8 | −0.4 (3) |
C1—N1—C5—C4 | 1.9 (3) | C9—C8—C13—C12 | 1.0 (3) |
C14—N1—C5—C4 | −177.3 (2) | C7—C8—C13—C12 | −179.6 (2) |
C1—N1—C5—C6 | −178.8 (2) | O2—S1—C17—C18 | −39.6 (2) |
C14—N1—C5—C6 | 2.0 (3) | O3—S1—C17—C18 | −161.15 (18) |
C3—C4—C5—N1 | −1.6 (3) | O1—S1—C17—C18 | 80.12 (19) |
C3—C4—C5—C6 | 179.1 (2) | O2—S1—C17—C22 | 142.77 (18) |
N1—C5—C6—C7 | 172.1 (2) | O3—S1—C17—C22 | 21.3 (2) |
C4—C5—C6—C7 | −8.6 (4) | O1—S1—C17—C22 | −97.47 (19) |
C5—C6—C7—C8 | −178.7 (2) | C22—C17—C18—C19 | 1.5 (3) |
C6—C7—C8—C9 | 178.2 (2) | S1—C17—C18—C19 | −176.11 (18) |
C6—C7—C8—C13 | −1.1 (4) | C17—C18—C19—C20 | −0.2 (3) |
C13—C8—C9—C10 | −0.5 (3) | C18—C19—C20—C21 | −0.5 (4) |
C7—C8—C9—C10 | −179.9 (2) | C18—C19—C20—Cl1 | 179.14 (18) |
C8—C9—C10—C11 | −0.5 (3) | C19—C20—C21—C22 | −0.1 (3) |
C15—N2—C11—C12 | 177.8 (2) | Cl1—C20—C21—C22 | −179.73 (17) |
C16—N2—C11—C12 | −9.1 (3) | C18—C17—C22—C21 | −2.1 (3) |
C15—N2—C11—C10 | −2.5 (3) | S1—C17—C22—C21 | 175.48 (17) |
C16—N2—C11—C10 | 170.6 (2) | C20—C21—C22—C17 | 1.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O3i | 0.88 (4) | 1.97 (4) | 2.831 (3) | 164 (3) |
O1W—H2W1···O1ii | 0.92 (5) | 2.04 (5) | 2.944 (3) | 167 (4) |
C1—H1A···O1Wiii | 0.93 | 2.24 | 3.170 (3) | 179 |
C2—H2A···O1Wiv | 0.93 | 2.44 | 3.229 (3) | 143 |
C4—H4A···O1v | 0.93 | 2.52 | 3.406 (2) | 160 |
C6—H6A···O2 | 0.93 | 2.55 | 3.453 (3) | 164 |
C13—H13A···O2 | 0.93 | 2.51 | 3.414 (3) | 164 |
C14—H14A···O2 | 0.96 | 2.51 | 3.106 (3) | 120 |
C14—H14B···O3vi | 0.96 | 2.58 | 3.393 (3) | 143 |
C9—H9A···Cg3v | 0.93 | 2.93 | 3.650 (2) | 135 |
C12—H12A···Cg3 | 0.93 | 2.95 | 3.760 (2) | 147 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z−1; (iv) −x, −y, −z+1; (v) x, y−1, z; (vi) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H19N2+·C6H4ClO3S−·H2O |
Mr | 448.96 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 6.3895 (1), 9.8739 (2), 17.0074 (3) |
α, β, γ (°) | 95.721 (1), 90.500 (1), 91.260 (1) |
V (Å3) | 1067.32 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.31 × 0.10 × 0.05 |
Data collection | |
Diffractometer | Bruker APEX DUO CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.912, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23113, 6156, 4327 |
Rint | 0.065 |
(sin θ/λ)max (Å−1) | 0.702 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.135, 1.03 |
No. of reflections | 6156 |
No. of parameters | 282 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.47, −0.43 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O3i | 0.88 (4) | 1.97 (4) | 2.831 (3) | 164 (3) |
O1W—H2W1···O1ii | 0.92 (5) | 2.04 (5) | 2.944 (3) | 167 (4) |
C1—H1A···O1Wiii | 0.93 | 2.24 | 3.170 (3) | 179 |
C2—H2A···O1Wiv | 0.93 | 2.44 | 3.229 (3) | 143 |
C4—H4A···O1v | 0.93 | 2.52 | 3.406 (2) | 160 |
C6—H6A···O2 | 0.93 | 2.55 | 3.453 (3) | 164 |
C13—H13A···O2 | 0.93 | 2.51 | 3.414 (3) | 164 |
C14—H14A···O2 | 0.96 | 2.51 | 3.106 (3) | 120 |
C14—H14B···O3vi | 0.96 | 2.58 | 3.393 (3) | 143 |
C9—H9A···Cg3v | 0.93 | 2.93 | 3.650 (2) | 135 |
C12—H12A···Cg3 | 0.93 | 2.95 | 3.760 (2) | 147 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z−1; (iv) −x, −y, −z+1; (v) x, y−1, z; (vi) x−1, y, z. |
Footnotes
1This paper is dedicated to the late His Majesty King Chulalongkorn (King Rama V) of Thailand for his numerous reforms to modernize the country on the occasion of Chulalongkorn Day (Piyamaharaj Day) which fell on the 23rd October.
‡Thomson Reuters ResearcherID: A-3561-2009.
§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.
Acknowledgements
Financial support by Prince of Songkla University is gratefully acknowledged. The authors also thank the Universiti Sains Malaysia for Research University grant No. 1001/PFIZIK/811160.
References
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Our research group have designed and synthesized some quaternary ammonium compounds including pyridinium derivatives. However, there are very few researches in the area of styryl pyridinium dyes being used as antibacterial agents. Based on the knowledge gathered since a very long time ago (Armitage et al., 1929; Browning et al., 1922; Wainwright & Kristiansen, 2003), we found that styryl pyridinium compounds possess high activity against both susceptible and methicillin-resistant Staphylococcus aureus (MRSA) (Chanawanno et al., 2010). This interesting anti-MRSA activity of the styryl pyridinium compounds trigger an encouragement to perform further investigation of these compounds in order to act against the powerful superbug MRSA which can overcome commonly used antibacterial drugs (Wainwright, 2008). Our bacterial assay results show that the title compound was moderately active against MRSA with the minimum inhibition concentration (MIC) = 37.5 µg/ml. Herein its crystal structure is reported.
Fig. 1 shows the asymmetric unit of the title compound (I) which consists of the C16H19N2+ cation, C6H4ClO3S- anion and one H2O molecule. The cation exists in the E configuration with respect to the C6═C7 double bond [1.349 (3) Å]. The cation is slightly twisted with the dihedral angle between the C1–C5/N1 pyridinium and the C8–C13 benzene rings being 9.33 (10)° and with the torsion angles C5—C6—C7—C8 = -178.7 (2)°. The two methyl groups of dimethylamino moiety are slightly twisted from the mean plane of the attached C8–C13 ring as indicated by the torsion angles C15—N2—C11—C10 = -2.5 (3)° and C16—N2—C11—C12 = -9.1 (3)°. The cation and anion are inclined to each other which indicated by the dihedral angles between the C17–C22 benzene ring of anion and pyridinium and C8–C13 benzene rings of cation being 79.19 (10) and 70.20 (10)°, respectively. The bond lengths (Allen et al., 1987) and angles in (I) are in normal ranges and comparable with a related structure (Chantrapromma et al., 2010).
In the crystal packing, all O atoms of the sulfonate group are involved in weak C—H···O interactions (Table 1). The cation is linked to both the anion and water molecule by weak C—H···O interactions, and the anion is linked to the water molecule by O—H···O hydrogen bond. These three molecules are linked into chains along the b axis (Table 1, Fig. 2). These chains are stacked along the the a axis (Fig. 2) by π–π interactions with the distances Cg1···Cg1 = 3.6429 (12) Å (symmetry code: -x, -y, -z) and Cg1···Cg2 = 3.6879 (12) Å (symmetry code: -1 + x, y, z). C—H···π interactions were also observed (Table 1); Cg1, Cg2 and Cg3 are the centroids of the C1–C5/N1, C8–C13 and C17–C22 rings, respectively.