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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Pages o2992-o2993
https://doi.org/10.1107/S1600536810043230

2-[(E)-4-(Di­methyl­amino)­styr­yl]-1-methyl­pyridinium 4-chloro­benzene­sulfonate monohydrate1

Hoong-Kun Fun,a*‡ Kullapa Chanawannob and Suchada Chantraprommab§

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

(Received 20 October 2010; accepted 23 October 2010; online 31 October 2010)

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 crystal structure, 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[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For background to and application of quarternary ammonium compounds, see: Armitage et al. (1929[Armitage, G., Gordon, J., Cohen, J. B. & Ellingworth, S. (1929). Lancet, 2, 968-971.]); Browning et al. (1922[Browning, C. H., Cohen, J. B. & Gulbransen, R. (1922). Br. Med. J. 1, 514-515.]); Chanawanno et al. (2010[Chanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010). Eur. J. Med. Chem. 45, 4199-4208.]); Wainwright & Kristiansen (2003[Wainwright, M. & Kristiansen, J. E. (2003). Int. J. Antimicrob. Agents, 22, 479-486.]); Wainwright (2008[Wainwright, M. (2008). Dyes Pigm. 76, 582-589.]). For a related structure, see: Chantra­promma et al. (2010[Chantrapromma, S., Chanawanno, K. & Fun, H.-K. (2010). Acta Cryst. E66, o1975-o1976.]). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C16H19N2+·C6H4ClO3S−·H2O

  • Mr = 448.96

  • Triclinic, [P \overline 1]

  • a = 6.3895 (1) Å

  • b = 9.8739 (2) Å

  • c = 17.0074 (3) Å

  • α = 95.721 (1)°

  • β = 90.500 (1)°

  • γ = 91.260 (1)°

  • V = 1067.32 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 100 K

  • 0.31 × 0.10 × 0.05 mm
Data collection

  • Bruker APEX DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.912, Tmax = 0.984

  • 23113 measured reflections

  • 6156 independent reflections

  • 4327 reflections with I > 2σ(I)

  • Rint = 0.065
Refinement

  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.135

  • S = 1.03

  • 6156 reflections

  • 282 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.47 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C17–C22 ring.
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.

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810043230/hb5695sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043230/hb5695Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

For bond lengths and angles, see Allen et al. (1987). For background to and application of quarternary ammonium compounds, 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 top

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.

Refinement top

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.

Structure description top

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.

For bond lengths and angles, see Allen et al. (1987). For background to and application of quarternary ammonium compounds, 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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I) showing 50% probability displacement ellipsoids.
[Figure 2] 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.
2-[(E)-4-(Dimethylamino)styryl]-1-methylpyridinium 4-chlorobenzenesulfonate monohydrate top
Crystal data top
C16H19N2+·C6H4ClO3S−·H2OZ = 2
Mr = 448.96F(000) = 472
Triclinic, P1Dx = 1.397 Mg m−3
Hall symbol: -P 1Melting point = 516–517 K
a = 6.3895 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.8739 (2) ÅCell parameters from 6156 reflections
c = 17.0074 (3) Åθ = 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) Å30.31 × 0.10 × 0.05 mm
Data collection top
Bruker APEX DUO CCD
diffractometer		6156 independent reflections
Radiation source: sealed tube4327 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
φ and ω scansθmax = 30.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −8→8
Tmin = 0.912, Tmax = 0.984k = −12→13
23113 measured reflectionsl = −23→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H 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 parametersΔρmax = 0.47 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
C16H19N2+·C6H4ClO3S−·H2Oγ = 91.260 (1)°
Mr = 448.96V = 1067.32 (3) Å3
Triclinic, P1Z = 2
a = 6.3895 (1) ÅMo Kα radiation
b = 9.8739 (2) ŵ = 0.31 mm−1
c = 17.0074 (3) ÅT = 100 K
α = 95.721 (1)°0.31 × 0.10 × 0.05 mm
β = 90.500 (1)°
Data collection top
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 = 0.984Rint = 0.065
23113 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.47 e Å−3
6156 reflectionsΔρmin = −0.43 e Å−3
282 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.0246 (3)0.11936 (19)0.10897 (11)0.0156 (4)
N21.2149 (3)0.17645 (19)0.39494 (11)0.0193 (4)
C1−0.1576 (3)0.0753 (2)0.07232 (13)0.0173 (4)
H1A−0.24170.13740.05000.021*
C2−0.2199 (3)−0.0591 (2)0.06768 (13)0.0188 (5)
H2A−0.3458−0.08810.04310.023*
C3−0.0922 (3)−0.1511 (2)0.10026 (13)0.0189 (5)
H3A−0.1307−0.24290.09690.023*
C40.0920 (3)−0.1056 (2)0.13766 (13)0.0174 (4)
H4A0.1774−0.16760.15940.021*
C50.1533 (3)0.0327 (2)0.14361 (12)0.0157 (4)
C60.3439 (3)0.0866 (2)0.18323 (13)0.0167 (4)
H6A0.38300.17670.17850.020*
C70.4671 (3)0.0127 (2)0.22659 (13)0.0167 (4)
H7A0.4256−0.07760.22940.020*
C80.6572 (3)0.0584 (2)0.26937 (13)0.0162 (4)
C90.7629 (3)−0.0320 (2)0.31341 (13)0.0173 (4)
H9A0.7088−0.12010.31430.021*
C100.9449 (3)0.0052 (2)0.35563 (13)0.0181 (4)
H10A1.0101−0.05730.38450.022*
C111.0323 (3)0.1382 (2)0.35494 (13)0.0161 (4)
C120.9253 (3)0.2302 (2)0.31130 (13)0.0168 (4)
H12A0.97840.31850.31030.020*
C130.7425 (3)0.1910 (2)0.26998 (13)0.0162 (4)
H13A0.67470.25370.24200.019*
C140.0814 (4)0.2658 (2)0.10930 (14)0.0198 (5)
H14A0.10170.30530.16280.030*
H14B−0.02910.31150.08490.030*
H14C0.20840.27540.08040.030*
C151.3197 (4)0.0833 (3)0.44178 (15)0.0237 (5)
H15A1.22600.05540.48130.036*
H15B1.44120.12780.46700.036*
H15C1.36140.00480.40820.036*
C161.3169 (3)0.3058 (2)0.38333 (14)0.0204 (5)
H16A1.32900.31400.32780.031*
H16B1.45380.30980.40720.031*
H16C1.23520.37890.40730.031*
Cl11.18810 (10)0.69360 (7)0.46691 (4)0.02879 (16)
S10.57475 (8)0.54114 (6)0.17948 (3)0.01647 (13)
O10.4692 (2)0.66863 (16)0.17231 (10)0.0204 (3)
O20.4357 (3)0.43430 (17)0.20239 (10)0.0249 (4)
O30.7023 (3)0.50131 (18)0.11086 (10)0.0247 (4)
C170.7541 (3)0.5767 (2)0.26013 (13)0.0164 (4)
C180.6803 (3)0.5782 (2)0.33656 (13)0.0192 (5)
H18A0.54090.55540.34510.023*
C190.8147 (4)0.6137 (2)0.40055 (14)0.0209 (5)
H19A0.76630.61530.45200.025*
C201.0214 (3)0.6468 (2)0.38611 (13)0.0190 (5)
C211.0976 (3)0.6445 (2)0.31068 (14)0.0204 (5)
H21A1.23710.66720.30240.024*
C220.9634 (3)0.6076 (2)0.24660 (14)0.0184 (4)
H22A1.01340.60370.19530.022*
O1W0.5623 (3)0.29024 (19)0.99640 (12)0.0270 (4)
H1W10.595 (5)0.366 (4)1.026 (2)0.054 (10)*
H2W10.552 (6)0.317 (4)0.946 (3)0.075 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0147 (8)0.0158 (9)0.0156 (9)−0.0006 (7)−0.0013 (7)−0.0013 (7)
N20.0156 (9)0.0188 (10)0.0236 (10)−0.0026 (7)−0.0070 (7)0.0046 (8)
C10.0133 (9)0.0227 (11)0.0157 (10)0.0012 (8)−0.0015 (8)0.0004 (9)
C20.0155 (10)0.0239 (12)0.0164 (11)−0.0026 (9)−0.0017 (8)−0.0008 (9)
C30.0196 (10)0.0178 (11)0.0188 (11)−0.0048 (9)−0.0009 (8)0.0002 (9)
C40.0171 (10)0.0168 (11)0.0183 (11)0.0001 (8)−0.0018 (8)0.0018 (8)
C50.0132 (9)0.0197 (11)0.0139 (10)0.0018 (8)−0.0010 (8)−0.0002 (8)
C60.0150 (10)0.0157 (10)0.0189 (11)−0.0024 (8)−0.0010 (8)0.0004 (8)
C70.0157 (10)0.0138 (10)0.0198 (11)−0.0014 (8)−0.0010 (8)−0.0014 (8)
C80.0146 (10)0.0174 (11)0.0161 (10)0.0016 (8)−0.0005 (8)−0.0006 (8)
C90.0181 (10)0.0134 (10)0.0200 (11)−0.0015 (8)−0.0005 (8)0.0000 (8)
C100.0200 (10)0.0162 (11)0.0185 (11)0.0022 (8)−0.0028 (8)0.0040 (8)
C110.0137 (9)0.0202 (11)0.0139 (10)−0.0008 (8)−0.0008 (8)−0.0010 (8)
C120.0164 (10)0.0167 (11)0.0171 (10)−0.0023 (8)−0.0007 (8)0.0012 (8)
C130.0162 (10)0.0173 (11)0.0153 (10)0.0013 (8)−0.0004 (8)0.0025 (8)
C140.0194 (10)0.0152 (11)0.0249 (12)−0.0007 (8)−0.0031 (9)0.0024 (9)
C150.0183 (11)0.0275 (13)0.0260 (12)−0.0007 (9)−0.0068 (9)0.0073 (10)
C160.0182 (10)0.0220 (11)0.0205 (11)−0.0047 (9)−0.0029 (8)0.0005 (9)
Cl10.0305 (3)0.0304 (3)0.0238 (3)−0.0009 (3)−0.0125 (2)−0.0040 (2)
S10.0171 (3)0.0136 (3)0.0182 (3)−0.00053 (19)−0.0044 (2)−0.0003 (2)
O10.0215 (8)0.0158 (8)0.0239 (9)0.0022 (6)−0.0041 (6)0.0017 (6)
O20.0251 (8)0.0192 (8)0.0306 (10)−0.0073 (7)−0.0091 (7)0.0056 (7)
O30.0225 (8)0.0312 (10)0.0187 (8)0.0052 (7)−0.0026 (6)−0.0070 (7)
C170.0186 (10)0.0104 (10)0.0199 (11)0.0008 (8)−0.0036 (8)0.0004 (8)
C180.0173 (10)0.0202 (11)0.0202 (11)−0.0008 (9)0.0001 (8)0.0023 (9)
C190.0257 (11)0.0207 (11)0.0159 (11)0.0005 (9)0.0002 (9)0.0001 (9)
C200.0212 (11)0.0161 (11)0.0191 (11)0.0019 (9)−0.0061 (9)−0.0014 (9)
C210.0159 (10)0.0183 (11)0.0266 (12)−0.0019 (9)−0.0048 (9)0.0013 (9)
C220.0207 (11)0.0166 (11)0.0180 (11)0.0011 (9)−0.0005 (8)0.0013 (9)
O1W0.0358 (10)0.0209 (9)0.0238 (10)−0.0001 (8)−0.0092 (8)0.0010 (8)
Geometric parameters (Å, º) top
N1—C11.358 (3)C13—H13A0.9300
N1—C51.371 (3)C14—H14A0.9600
N1—C141.482 (3)C14—H14B0.9600
N2—C111.372 (2)C14—H14C0.9600
N2—C151.447 (3)C15—H15A0.9600
N2—C161.452 (3)C15—H15B0.9600
C1—C21.372 (3)C15—H15C0.9600
C1—H1A0.9300C16—H16A0.9600
C2—C31.387 (3)C16—H16B0.9600
C2—H2A0.9300C16—H16C0.9600
C3—C41.378 (3)Cl1—C201.750 (2)
C3—H3A0.9300S1—O21.4495 (17)
C4—C51.406 (3)S1—O31.4562 (18)
C4—H4A0.9300S1—O11.4561 (16)
C5—C61.451 (3)S1—C171.782 (2)
C6—C71.349 (3)C17—C181.386 (3)
C6—H6A0.9300C17—C221.391 (3)
C7—C81.451 (3)C18—C191.392 (3)
C7—H7A0.9300C18—H18A0.9300
C8—C91.402 (3)C19—C201.383 (3)
C8—C131.406 (3)C19—H19A0.9300
C9—C101.385 (3)C20—C211.374 (3)
C9—H9A0.9300C21—C221.395 (3)
C10—C111.417 (3)C21—H21A0.9300
C10—H10A0.9300C22—H22A0.9300
C11—C121.413 (3)O1W—H1W10.88 (4)
C12—C131.386 (3)O1W—H2W10.91 (4)
C12—H12A0.9300
C1—N1—C5121.90 (19)C8—C13—H13A119.2
C1—N1—C14117.25 (18)N1—C14—H14A109.5
C5—N1—C14120.85 (17)N1—C14—H14B109.5
C11—N2—C15120.73 (19)H14A—C14—H14B109.5
C11—N2—C16119.76 (18)N1—C14—H14C109.5
C15—N2—C16119.16 (17)H14A—C14—H14C109.5
N1—C1—C2121.1 (2)H14B—C14—H14C109.5
N1—C1—H1A119.4N2—C15—H15A109.5
C2—C1—H1A119.4N2—C15—H15B109.5
C1—C2—C3118.99 (19)H15A—C15—H15B109.5
C1—C2—H2A120.5N2—C15—H15C109.5
C3—C2—H2A120.5H15A—C15—H15C109.5
C4—C3—C2119.6 (2)H15B—C15—H15C109.5
C4—C3—H3A120.2N2—C16—H16A109.5
C2—C3—H3A120.2N2—C16—H16B109.5
C3—C4—C5121.2 (2)H16A—C16—H16B109.5
C3—C4—H4A119.4N2—C16—H16C109.5
C5—C4—H4A119.4H16A—C16—H16C109.5
N1—C5—C4117.15 (18)H16B—C16—H16C109.5
N1—C5—C6119.21 (19)O2—S1—O3114.41 (11)
C4—C5—C6123.64 (19)O2—S1—O1113.10 (10)
C7—C6—C5123.3 (2)O3—S1—O1112.03 (10)
C7—C6—H6A118.3O2—S1—C17105.34 (10)
C5—C6—H6A118.3O3—S1—C17105.74 (10)
C6—C7—C8127.2 (2)O1—S1—C17105.26 (10)
C6—C7—H7A116.4C18—C17—C22120.5 (2)
C8—C7—H7A116.4C18—C17—S1118.96 (16)
C9—C8—C13117.25 (18)C22—C17—S1120.51 (18)
C9—C8—C7119.4 (2)C17—C18—C19120.0 (2)
C13—C8—C7123.38 (19)C17—C18—H18A120.0
C10—C9—C8122.3 (2)C19—C18—H18A120.0
C10—C9—H9A118.9C20—C19—C18118.8 (2)
C8—C9—H9A118.9C20—C19—H19A120.6
C9—C10—C11120.26 (19)C18—C19—H19A120.6
C9—C10—H10A119.9C21—C20—C19121.9 (2)
C11—C10—H10A119.9C21—C20—Cl1119.68 (17)
N2—C11—C12121.0 (2)C19—C20—Cl1118.42 (18)
N2—C11—C10121.27 (19)C20—C21—C22119.3 (2)
C12—C11—C10117.72 (18)C20—C21—H21A120.4
C13—C12—C11121.0 (2)C22—C21—H21A120.4
C13—C12—H12A119.5C17—C22—C21119.5 (2)
C11—C12—H12A119.5C17—C22—H22A120.3
C12—C13—C8121.5 (2)C21—C22—H22A120.3
C12—C13—H13A119.2H1W1—O1W—H2W1104 (3)
C5—N1—C1—C2−0.7 (3)C9—C10—C11—N2−178.6 (2)
C14—N1—C1—C2178.5 (2)C9—C10—C11—C121.1 (3)
N1—C1—C2—C3−0.8 (3)N2—C11—C12—C13179.1 (2)
C1—C2—C3—C41.1 (3)C10—C11—C12—C13−0.7 (3)
C2—C3—C4—C50.1 (3)C11—C12—C13—C8−0.4 (3)
C1—N1—C5—C41.9 (3)C9—C8—C13—C121.0 (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—C62.0 (3)O3—S1—C17—C18−161.15 (18)
C3—C4—C5—N1−1.6 (3)O1—S1—C17—C1880.12 (19)
C3—C4—C5—C6179.1 (2)O2—S1—C17—C22142.77 (18)
N1—C5—C6—C7172.1 (2)O3—S1—C17—C2221.3 (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—C191.5 (3)
C6—C7—C8—C9178.2 (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—Cl1179.14 (18)
C8—C9—C10—C11−0.5 (3)C19—C20—C21—C22−0.1 (3)
C15—N2—C11—C12177.8 (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—C21175.48 (17)
C16—N2—C11—C10170.6 (2)C20—C21—C22—C171.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O3i0.88 (4)1.97 (4)2.831 (3)164 (3)
O1W—H2W1···O1ii0.92 (5)2.04 (5)2.944 (3)167 (4)
C1—H1A···O1Wiii0.932.243.170 (3)179
C2—H2A···O1Wiv0.932.443.229 (3)143
C4—H4A···O1v0.932.523.406 (2)160
C6—H6A···O20.932.553.453 (3)164
C13—H13A···O20.932.513.414 (3)164
C14—H14A···O20.962.513.106 (3)120
C14—H14B···O3vi0.962.583.393 (3)143
C9—H9A···Cg3v0.932.933.650 (2)135
C12—H12A···Cg30.932.953.760 (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 formulaC16H19N2+·C6H4ClO3S−·H2O
Mr448.96
Crystal system, space groupTriclinic, 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)
Z2
Radiation typeMo Kα
µ (mm−1)0.31
Crystal size (mm)0.31 × 0.10 × 0.05
Data collection
DiffractometerBruker APEX DUO CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.912, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		23113, 6156, 4327
Rint0.065
(sin θ/λ)max (Å−1)0.702
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.135, 1.03
No. of reflections6156
No. of parameters282
H-atom treatmentH 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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O3i0.88 (4)1.97 (4)2.831 (3)164 (3)
O1W—H2W1···O1ii0.92 (5)2.04 (5)2.944 (3)167 (4)
C1—H1A···O1Wiii0.932.243.170 (3)179
C2—H2A···O1Wiv0.932.443.229 (3)143
C4—H4A···O1v0.932.523.406 (2)160
C6—H6A···O20.932.553.453 (3)164
C13—H13A···O20.932.513.414 (3)164
C14—H14A···O20.962.513.106 (3)120
C14—H14B···O3vi0.962.583.393 (3)143
C9—H9A···Cg3v0.932.933.650 (2)135
C12—H12A···Cg30.932.953.760 (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

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationArmitage, G., Gordon, J., Cohen, J. B. & Ellingworth, S. (1929). Lancet, 2, 968–971.  CrossRef Google Scholar
 First citationBrowning, C. H., Cohen, J. B. & Gulbransen, R. (1922). Br. Med. J. 1, 514–515.  CrossRef CAS PubMed Google Scholar
 First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010). Eur. J. Med. Chem. 45, 4199–4208.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationChantrapromma, S., Chanawanno, K. & Fun, H.-K. (2010). Acta Cryst. E66, o1975–o1976.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWainwright, M. (2008). Dyes Pigm. 76, 582–589.  Web of Science CrossRef CAS Google Scholar
 First citationWainwright, M. & Kristiansen, J. E. (2003). Int. J. Antimicrob. Agents, 22, 479–486.  Web of Science CrossRef PubMed CAS Google Scholar

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Pages o2992-o2993
https://doi.org/10.1107/S1600536810043230
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