Literature DB >> 24098203

(E)-2-[4-(Di-ethyl-amino)-styr-yl]-1-methyl-quinolinium 4-fluoro-benzene-sulfonate monohydrate.

Hoong-Kun Fun1, Narissara Kaewmanee, Kullapa Chanawanno, Nawong Boonnak, Suchada Chantrapromma.   

Abstract

In the title hydrated molecular salt, C22H25N2 (+)·C6H4FO3S(-)·H2O, the cation displays whole mol-ecule disorder over two sets of sites in a 0.780 (5):0.220 (5) ratio. The quinolinium ring system is essentially planar, with r.m.s. deviations of 0.0162 and 0.0381 Å for the major and minor disorder components, respectively. The dihedral angles between the mean plane of the quinolinium ring system and the benzene ring are 5.1 (3) and 7.7 (11)°, respectively, for the major and minor components in the cation. In the crystal, cations, anions and water mol-ecules are linked into chains along [010] by O-H⋯O hydrogen bonds and are further connected into a three-dimensional network by weak C-H⋯O and C-H⋯F inter-actions. In addition, π-π inter-actions with centroid-centroid distances of 3.634 (3), 3.702 (5) and 3.838 (5) Å are observed.

Entities:  

Year:  2013        PMID： 24098203      PMCID： PMC3790381          DOI： 10.1107/S1600536813023532

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to and applications of quarternary ammonium compounds, see: Babalola (1998 ▶); Collier et al. (1953 ▶); Gutsulyak (1972 ▶); Chanawanno et al. (2010a ▶,b ▶). For related structures, see: Fun et al. (2010 ▶, 2011 ▶); Kaewmanee et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H25N2 +·C6H4FO3S−·H2O M = 510.62 Monoclinic, a = 13.366 (2) Å b = 10.2326 (17) Å c = 19.891 (3) Å β = 113.004 (8)° V = 2504.1 (7) Å3 Z = 4 Mo Kα radiation μ = 0.18 mm−1 T = 100 K 0.29 × 0.18 × 0.10 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.951, T max = 0.982 13569 measured reflections 4396 independent reflections 3379 reflections with I > 2σ(I) R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.058 wR(F 2) = 0.172 S = 1.04 4396 reflections 427 parameters 761 restraints H-atom parameters constrained Δρmax = 0.74 e Å−3 Δρmin = −0.48 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: 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, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813023532/lh5643sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023532/lh5643Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813023532/lh5643Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H25N2+·C6H4FO3S−·H2OF(000) = 1080
Mr = 510.62Dx = 1.354 Mg m−3
Monoclinic, P21/cMelting point = 503–505 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 13.366 (2) ÅCell parameters from 4396 reflections
b = 10.2326 (17) Åθ = 1.7–25.0°
c = 19.891 (3) ŵ = 0.18 mm−1
β = 113.004 (8)°T = 100 K
V = 2504.1 (7) Å3Needle, purple
Z = 40.29 × 0.18 × 0.10 mm
Bruker SMART APEXII DUO CCD area-detector diffractometer4396 independent reflections
Radiation source: fine-focus sealed tube3379 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −15→15
Tmin = 0.951, Tmax = 0.982k = −12→12
13569 measured reflectionsl = −23→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0816P)2 + 2.6528P] where P = (Fo2 + 2Fc2)/3
4396 reflections(Δ/σ)max = 0.001
427 parametersΔρmax = 0.74 e Å−3
761 restraintsΔρmin = −0.48 e Å−3
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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
xyzUiso*/UeqOcc. (<1)
N1A0.5759 (6)0.6654 (9)1.0560 (3)0.0378 (13)0.780 (5)
N2A0.0845 (3)1.3098 (4)0.89515 (18)0.0513 (11)0.780 (5)
C1A0.6440 (4)0.5581 (6)1.0605 (3)0.0354 (13)0.780 (5)
C2A0.6899 (4)0.4835 (6)1.1236 (3)0.0447 (12)0.780 (5)
H2AA0.67670.50281.16510.054*0.780 (5)
C3A0.7542 (4)0.3818 (5)1.1228 (3)0.0485 (12)0.780 (5)
H3AA0.78590.33221.16500.058*0.780 (5)
C4A0.7751 (5)0.3483 (6)1.0623 (3)0.0456 (14)0.780 (5)
H4AA0.82110.27851.06510.055*0.780 (5)
C5A0.7293 (7)0.4160 (7)0.9987 (4)0.0400 (15)0.780 (5)
H5AA0.74230.39230.95770.048*0.780 (5)
C6A0.6608 (8)0.5245 (8)0.9965 (4)0.0383 (15)0.780 (5)
C7A0.6110 (7)0.5995 (10)0.9331 (4)0.0435 (17)0.780 (5)
H7AA0.62400.58000.89150.052*0.780 (5)
C8A0.5442 (6)0.7001 (9)0.9315 (4)0.0421 (17)0.780 (5)
H8AA0.51160.74810.88880.050*0.780 (5)
C9A0.5227 (9)0.7340 (11)0.9940 (4)0.0374 (16)0.780 (5)
C10A0.4479 (6)0.8365 (9)0.9914 (4)0.0381 (15)0.780 (5)
H10A0.44070.85821.03470.046*0.780 (5)
C11A0.3881 (6)0.9027 (7)0.9316 (4)0.0352 (15)0.780 (5)
H11A0.40130.88440.89000.042*0.780 (5)
C12A0.3052 (7)0.9996 (10)0.9231 (4)0.0366 (16)0.780 (5)
C13A0.2533 (4)1.0610 (6)0.8559 (3)0.0406 (13)0.780 (5)
H13A0.27001.03520.81660.049*0.780 (5)
C14A0.1781 (4)1.1590 (5)0.8458 (2)0.0449 (11)0.780 (5)
H14A0.14421.19600.79970.054*0.780 (5)
C15A0.1513 (4)1.2045 (5)0.9036 (2)0.0413 (10)0.780 (5)
C16A0.2008 (4)1.1394 (5)0.9701 (2)0.0409 (12)0.780 (5)
H16A0.18181.16131.00890.049*0.780 (5)
C17A0.2768 (5)1.0439 (6)0.9792 (3)0.0415 (15)0.780 (5)
H17A0.31111.00701.02520.050*0.780 (5)
C18A0.0513 (4)1.3506 (5)0.9530 (2)0.0514 (12)0.780 (5)
H18A0.02811.44100.94430.062*0.780 (5)
H18B0.11461.34770.99870.062*0.780 (5)
C19A−0.0402 (4)1.2713 (6)0.9629 (3)0.0591 (14)0.780 (5)
H19A−0.05281.30461.00400.089*0.780 (5)
H19B−0.01911.18110.97120.089*0.780 (5)
H19C−0.10551.27870.91970.089*0.780 (5)
C20A0.0338 (4)1.3769 (5)0.8250 (3)0.0540 (12)0.780 (5)
H20A0.08711.38740.80340.065*0.780 (5)
H20B0.01101.46340.83320.065*0.780 (5)
C21A−0.0621 (4)1.3048 (6)0.7728 (3)0.0648 (14)0.780 (5)
H21A−0.08211.34060.72470.097*0.780 (5)
H21B−0.12191.31320.78770.097*0.780 (5)
H21C−0.04401.21410.77230.097*0.780 (5)
C22A0.5617 (8)0.7009 (9)1.1235 (4)0.060 (2)0.780 (5)
H22A0.54130.79121.12130.089*0.780 (5)
H22B0.62880.68721.16470.089*0.780 (5)
H22C0.50590.64751.12830.089*0.780 (5)
N1B0.558 (3)0.667 (3)1.0533 (14)0.045 (5)*0.220 (5)
N2B0.0273 (10)1.2446 (12)0.8830 (6)0.043 (3)*0.220 (5)
C1B0.6367 (15)0.5738 (17)1.0603 (13)0.036 (4)*0.220 (5)
C2B0.7007 (16)0.5049 (19)1.1165 (13)0.059 (5)*0.220 (5)
H2BA0.68850.52691.15800.070*0.220 (5)
C3B0.7748 (17)0.417 (2)1.1319 (12)0.057 (5)*0.220 (5)
H3BA0.81390.38381.17840.068*0.220 (5)
C4B0.788 (2)0.376 (3)1.0676 (13)0.050 (5)*0.220 (5)
H4BA0.83370.30641.06910.061*0.220 (5)
C5B0.734 (3)0.440 (3)1.0039 (14)0.044 (5)*0.220 (5)
H5BA0.74560.41510.96270.052*0.220 (5)
C6B0.659 (3)0.544 (4)0.9966 (14)0.045 (5)*0.220 (5)
C7B0.593 (3)0.597 (3)0.9290 (14)0.039 (5)*0.220 (5)
H7BA0.59750.56580.88620.047*0.220 (5)
C8B0.524 (2)0.694 (3)0.9271 (14)0.032 (4)*0.220 (5)
H8BA0.48380.73430.88270.039*0.220 (5)
C9B0.510 (3)0.737 (4)0.9909 (14)0.034 (4)*0.220 (5)
C10B0.429 (3)0.834 (3)0.9861 (16)0.039 (5)*0.220 (5)
H10B0.41870.85621.02810.047*0.220 (5)
C11B0.370 (2)0.893 (3)0.9239 (16)0.036 (5)*0.220 (5)
H11B0.37930.86810.88160.043*0.220 (5)
C12B0.292 (3)0.994 (4)0.9199 (14)0.042 (5)*0.220 (5)
C13B0.2278 (17)1.040 (2)0.8512 (13)0.049 (5)*0.220 (5)
H13B0.24491.01570.81190.059*0.220 (5)
C14B0.1405 (13)1.1185 (17)0.8385 (9)0.044 (4)*0.220 (5)
H14B0.09691.14230.79080.052*0.220 (5)
C15B0.1149 (12)1.1647 (16)0.8973 (8)0.044 (4)*0.220 (5)
C16B0.1760 (15)1.108 (2)0.9659 (10)0.048 (5)*0.220 (5)
H16B0.16021.13091.00580.057*0.220 (5)
C17B0.2577 (18)1.020 (2)0.9755 (13)0.037 (5)*0.220 (5)
H17B0.29030.97711.02010.044*0.220 (5)
C18B−0.014 (2)1.276 (2)0.9409 (11)0.085 (6)*0.220 (5)
H18C−0.09231.28030.91830.102*0.220 (5)
H18D0.00531.20440.97540.102*0.220 (5)
C19B0.0258 (19)1.399 (2)0.9825 (12)0.088 (5)*0.220 (5)
H19D−0.03511.44860.98230.132*0.220 (5)
H19E0.06551.44850.96030.132*0.220 (5)
H19F0.07251.37791.03190.132*0.220 (5)
C20B−0.0412 (12)1.2854 (16)0.8110 (8)0.046 (4)*0.220 (5)
H20C−0.11141.30580.81210.055*0.220 (5)
H20D−0.05191.20970.77960.055*0.220 (5)
C21B−0.012 (2)1.396 (2)0.7738 (13)0.088 (5)*0.220 (5)
H21D−0.06571.40330.72480.132*0.220 (5)
H21E0.05781.38050.77270.132*0.220 (5)
H21F−0.01061.47530.79990.132*0.220 (5)
C22B0.533 (2)0.695 (3)1.1170 (15)0.045 (7)*0.220 (5)
H22D0.45670.71321.10160.067*0.220 (5)
H22E0.57420.76951.14240.067*0.220 (5)
H22F0.55160.62061.14890.067*0.220 (5)
S10.40215 (6)0.56285 (7)0.69386 (4)0.0354 (2)
F10.04851 (17)0.1870 (2)0.64756 (11)0.0674 (6)
O10.3504 (2)0.6701 (2)0.64418 (12)0.0549 (6)
O20.48201 (19)0.4957 (2)0.67312 (13)0.0545 (6)
O30.4401 (2)0.5969 (2)0.76877 (12)0.0552 (6)
C230.2963 (2)0.4464 (3)0.67789 (14)0.0361 (7)
C240.3173 (3)0.3131 (3)0.68582 (14)0.0379 (7)
H24A0.38790.28280.69830.045*
C250.2335 (3)0.2245 (3)0.67521 (15)0.0412 (7)
H25A0.24670.13510.68030.049*
C260.1313 (3)0.2732 (4)0.65717 (17)0.0481 (8)
C270.1072 (3)0.4044 (4)0.6492 (2)0.0581 (9)
H27A0.03640.43360.63730.070*
C280.1900 (3)0.4909 (4)0.65940 (18)0.0499 (8)
H28A0.17530.58000.65390.060*
O1W0.3226 (2)0.9163 (3)0.70409 (15)0.0648 (7)
H1W10.32160.83400.68320.097*
H2W10.37260.92200.75020.097*
U11U22U33U12U13U23
N1A0.037 (3)0.053 (2)0.0248 (17)−0.001 (2)0.0136 (18)0.0013 (14)
N2A0.064 (2)0.056 (2)0.0405 (18)0.014 (2)0.0270 (17)−0.0012 (17)
C1A0.031 (2)0.042 (3)0.032 (2)−0.0005 (18)0.0114 (16)−0.0020 (19)
C2A0.047 (2)0.059 (3)0.027 (2)−0.003 (2)0.0137 (17)0.0107 (19)
C3A0.046 (3)0.050 (3)0.041 (2)−0.009 (2)0.008 (2)0.004 (2)
C4A0.039 (3)0.040 (3)0.055 (3)−0.007 (2)0.015 (2)0.001 (2)
C5A0.036 (2)0.042 (4)0.047 (3)−0.005 (3)0.0215 (19)−0.007 (2)
C6A0.036 (2)0.042 (4)0.035 (2)−0.009 (2)0.0110 (15)0.002 (2)
C7A0.044 (4)0.061 (3)0.034 (2)−0.005 (3)0.024 (2)−0.0020 (19)
C8A0.037 (4)0.056 (3)0.035 (2)0.004 (3)0.016 (2)0.001 (2)
C9A0.035 (4)0.043 (3)0.028 (2)−0.008 (2)0.0059 (19)0.0067 (17)
C10A0.036 (3)0.053 (3)0.029 (2)−0.005 (2)0.017 (2)−0.0057 (18)
C11A0.039 (3)0.040 (3)0.030 (2)−0.008 (2)0.018 (2)−0.0060 (19)
C12A0.040 (3)0.041 (2)0.030 (2)−0.006 (2)0.0155 (19)−0.0029 (17)
C13A0.050 (3)0.046 (3)0.030 (2)0.007 (3)0.021 (2)0.0022 (19)
C14A0.055 (3)0.053 (3)0.0305 (19)0.013 (2)0.0199 (19)0.0087 (19)
C15A0.047 (2)0.044 (2)0.036 (2)0.002 (2)0.0196 (18)−0.0002 (18)
C16A0.044 (3)0.056 (3)0.0276 (19)−0.005 (2)0.0191 (18)−0.0061 (19)
C17A0.039 (3)0.057 (3)0.0267 (19)−0.004 (3)0.0111 (19)0.003 (2)
C18A0.065 (3)0.051 (3)0.051 (2)0.013 (2)0.036 (2)−0.009 (2)
C19A0.042 (2)0.086 (4)0.050 (3)0.003 (2)0.019 (2)−0.024 (3)
C20A0.058 (3)0.047 (3)0.058 (3)0.005 (2)0.024 (2)−0.003 (2)
C21A0.063 (3)0.068 (3)0.062 (3)0.007 (3)0.023 (3)0.003 (3)
C22A0.071 (6)0.082 (4)0.033 (3)0.020 (5)0.029 (3)0.006 (3)
S10.0494 (4)0.0337 (4)0.0266 (3)−0.0060 (3)0.0186 (3)0.0029 (3)
F10.0611 (12)0.0785 (15)0.0584 (12)−0.0244 (11)0.0188 (10)0.0086 (11)
O10.0774 (16)0.0423 (13)0.0472 (13)−0.0046 (12)0.0268 (12)0.0079 (11)
O20.0652 (15)0.0529 (14)0.0595 (14)−0.0084 (12)0.0398 (12)−0.0089 (12)
O30.0698 (15)0.0590 (15)0.0406 (12)−0.0161 (12)0.0254 (11)−0.0065 (11)
C230.0494 (17)0.0384 (16)0.0223 (12)−0.0012 (14)0.0160 (12)0.0002 (12)
C240.0490 (17)0.0416 (17)0.0255 (13)0.0001 (14)0.0172 (12)0.0020 (12)
C250.0591 (19)0.0381 (16)0.0292 (14)−0.0028 (15)0.0202 (13)0.0047 (13)
C260.0504 (19)0.057 (2)0.0358 (16)−0.0153 (17)0.0159 (14)0.0061 (15)
C270.049 (2)0.068 (3)0.060 (2)0.0066 (18)0.0236 (17)0.0137 (19)
C280.058 (2)0.0440 (18)0.0507 (19)0.0068 (16)0.0245 (16)0.0088 (16)
O1W0.0586 (15)0.0543 (15)0.0797 (18)0.0086 (12)0.0251 (13)−0.0061 (13)
N1A—C9A1.354 (5)C2B—H2BA0.9300
N1A—C1A1.406 (6)C3B—C4B1.420 (16)
N1A—C22A1.472 (5)C3B—H3BA0.9300
N2A—C15A1.366 (5)C4B—C5B1.361 (15)
N2A—C18A1.448 (5)C4B—H4BA0.9300
N2A—C20A1.463 (6)C5B—C6B1.427 (15)
C1A—C2A1.390 (6)C5B—H5BA0.9300
C1A—C6A1.420 (5)C6B—C7B1.394 (15)
C2A—C3A1.354 (6)C7B—C8B1.354 (15)
C2A—H2AA0.9300C7B—H7BA0.9300
C3A—C4A1.381 (6)C8B—C9B1.423 (15)
C3A—H3AA0.9300C8B—H8BA0.9300
C4A—C5A1.360 (6)C9B—C10B1.436 (15)
C4A—H4AA0.9300C10B—C11B1.323 (16)
C5A—C6A1.428 (6)C10B—H10B0.9300
C5A—H5AA0.9300C11B—C12B1.451 (15)
C6A—C7A1.403 (6)C11B—H11B0.9300
C7A—C8A1.356 (6)C12B—C17B1.382 (15)
C7A—H7AA0.9300C12B—C13B1.382 (15)
C8A—C9A1.423 (5)C13B—C14B1.357 (15)
C8A—H8AA0.9300C13B—H13B0.9300
C9A—C10A1.436 (6)C14B—C15B1.422 (14)
C10A—C11A1.330 (6)C14B—H14B0.9300
C10A—H10A0.9300C15B—C16B1.412 (15)
C11A—C12A1.447 (6)C16B—C17B1.370 (15)
C11A—H11A0.9300C16B—H16B0.9300
C12A—C17A1.387 (5)C17B—H17B0.9300
C12A—C13A1.393 (6)C18B—C19B1.478 (17)
C13A—C14A1.377 (6)C18B—H18C0.9700
C13A—H13A0.9300C18B—H18D0.9700
C14A—C15A1.410 (5)C19B—H19D0.9600
C14A—H14A0.9300C19B—H19E0.9600
C15A—C16A1.395 (5)C19B—H19F0.9600
C16A—C17A1.370 (6)C20B—C21B1.482 (16)
C16A—H16A0.9300C20B—H20C0.9700
C17A—H17A0.9300C20B—H20D0.9700
C18A—C19A1.543 (6)C21B—H21D0.9600
C18A—H18A0.9700C21B—H21E0.9600
C18A—H18B0.9700C21B—H21F0.9600
C19A—H19A0.9600C22B—H22D0.9600
C19A—H19B0.9600C22B—H22E0.9600
C19A—H19C0.9600C22B—H22F0.9600
C20A—C21A1.492 (6)S1—O31.417 (2)
C20A—H20A0.9700S1—O11.458 (2)
C20A—H20B0.9700S1—O21.458 (2)
C21A—H21A0.9600S1—C231.781 (3)
C21A—H21B0.9600F1—C261.369 (4)
C21A—H21C0.9600C23—C241.390 (4)
C22A—H22A0.9600C23—C281.398 (4)
C22A—H22B0.9600C24—C251.392 (4)
C22A—H22C0.9600C24—H24A0.9300
N1B—C9B1.355 (14)C25—C261.363 (5)
N1B—C1B1.393 (14)C25—H25A0.9300
N1B—C22B1.457 (15)C26—C271.375 (5)
N2B—C15B1.364 (13)C27—C281.369 (5)
N2B—C20B1.427 (14)C27—H27A0.9300
N2B—C18B1.492 (15)C28—H28A0.9300
C1B—C2B1.315 (14)O1W—H1W10.9377
C1B—C6B1.442 (15)O1W—H2W10.9007
C2B—C3B1.287 (15)
C9A—N1A—C1A124.0 (4)C7B—C6B—C1B120.0 (17)
C9A—N1A—C22A119.6 (5)C5B—C6B—C1B116.2 (15)
C1A—N1A—C22A116.4 (5)C8B—C7B—C6B118.4 (18)
C15A—N2A—C18A121.2 (3)C8B—C7B—H7BA120.8
C15A—N2A—C20A121.6 (3)C6B—C7B—H7BA120.8
C18A—N2A—C20A116.8 (3)C7B—C8B—C9B122.1 (18)
C2A—C1A—N1A122.2 (5)C7B—C8B—H8BA118.9
C2A—C1A—C6A120.5 (5)C9B—C8B—H8BA118.9
N1A—C1A—C6A117.2 (4)N1B—C9B—C8B118.3 (16)
C3A—C2A—C1A118.0 (4)N1B—C9B—C10B119.8 (17)
C3A—C2A—H2AA121.0C8B—C9B—C10B120.7 (17)
C1A—C2A—H2AA121.0C11B—C10B—C9B122 (2)
C2A—C3A—C4A123.2 (5)C11B—C10B—H10B119.0
C2A—C3A—H3AA118.4C9B—C10B—H10B119.0
C4A—C3A—H3AA118.4C10B—C11B—C12B122 (2)
C5A—C4A—C3A120.9 (5)C10B—C11B—H11B119.0
C5A—C4A—H4AA119.6C12B—C11B—H11B119.0
C3A—C4A—H4AA119.6C17B—C12B—C13B116.8 (16)
C4A—C5A—C6A118.3 (5)C17B—C12B—C11B123.5 (18)
C4A—C5A—H5AA120.8C13B—C12B—C11B117.1 (18)
C6A—C5A—H5AA120.8C14B—C13B—C12B123.1 (17)
C7A—C6A—C1A119.2 (5)C14B—C13B—H13B118.5
C7A—C6A—C5A121.7 (5)C12B—C13B—H13B118.5
C1A—C6A—C5A119.0 (4)C13B—C14B—C15B120.6 (15)
C8A—C7A—C6A120.8 (5)C13B—C14B—H14B119.7
C8A—C7A—H7AA119.6C15B—C14B—H14B119.7
C6A—C7A—H7AA119.6N2B—C15B—C16B125.0 (13)
C7A—C8A—C9A121.4 (6)N2B—C15B—C14B119.3 (12)
C7A—C8A—H8AA119.3C16B—C15B—C14B115.0 (13)
C9A—C8A—H8AA119.3C17B—C16B—C15B122.3 (16)
N1A—C9A—C8A117.1 (5)C17B—C16B—H16B118.8
N1A—C9A—C10A121.5 (5)C15B—C16B—H16B118.8
C8A—C9A—C10A121.4 (5)C16B—C17B—C12B120.8 (17)
C11A—C10A—C9A124.8 (5)C16B—C17B—H17B119.6
C11A—C10A—H10A117.6C12B—C17B—H17B119.6
C9A—C10A—H10A117.6C19B—C18B—N2B117.3 (18)
C10A—C11A—C12A128.2 (5)C19B—C18B—H18C108.0
C10A—C11A—H11A115.9N2B—C18B—H18C108.0
C12A—C11A—H11A115.9C19B—C18B—H18D108.0
C17A—C12A—C13A115.7 (5)N2B—C18B—H18D108.0
C17A—C12A—C11A124.6 (5)H18C—C18B—H18D107.2
C13A—C12A—C11A119.5 (5)C18B—C19B—H19D109.5
C14A—C13A—C12A121.9 (4)C18B—C19B—H19E109.5
C14A—C13A—H13A119.0H19D—C19B—H19E109.5
C12A—C13A—H13A119.0C18B—C19B—H19F109.5
C13A—C14A—C15A121.7 (4)H19D—C19B—H19F109.5
C13A—C14A—H14A119.1H19E—C19B—H19F109.5
C15A—C14A—H14A119.1N2B—C20B—C21B122.3 (15)
N2A—C15A—C16A122.5 (3)N2B—C20B—H20C106.8
N2A—C15A—C14A121.5 (4)C21B—C20B—H20C106.8
C16A—C15A—C14A115.9 (4)N2B—C20B—H20D106.8
C17A—C16A—C15A121.2 (4)C21B—C20B—H20D106.8
C17A—C16A—H16A119.4H20C—C20B—H20D106.6
C15A—C16A—H16A119.4C20B—C21B—H21D109.5
C16A—C17A—C12A123.3 (5)C20B—C21B—H21E109.5
C16A—C17A—H17A118.3H21D—C21B—H21E109.5
C12A—C17A—H17A118.3C20B—C21B—H21F109.5
N2A—C18A—C19A117.0 (4)H21D—C21B—H21F109.5
N2A—C18A—H18A108.0H21E—C21B—H21F109.5
C19A—C18A—H18A108.0N1B—C22B—H22D109.5
N2A—C18A—H18B108.0N1B—C22B—H22E109.5
C19A—C18A—H18B108.0H22D—C22B—H22E109.5
H18A—C18A—H18B107.3N1B—C22B—H22F109.5
N2A—C20A—C21A112.5 (4)H22D—C22B—H22F109.5
N2A—C20A—H20A109.1H22E—C22B—H22F109.5
C21A—C20A—H20A109.1O3—S1—O1114.07 (15)
N2A—C20A—H20B109.1O3—S1—O2114.35 (15)
C21A—C20A—H20B109.1O1—S1—O2111.62 (14)
H20A—C20A—H20B107.8O3—S1—C23106.58 (13)
C9B—N1B—C1B121.5 (16)O1—S1—C23104.45 (14)
C9B—N1B—C22B120.5 (17)O2—S1—C23104.65 (14)
C1B—N1B—C22B117.9 (17)C24—C23—C28119.3 (3)
C15B—N2B—C20B123.2 (11)C24—C23—S1121.7 (2)
C15B—N2B—C18B120.8 (13)C28—C23—S1119.0 (2)
C20B—N2B—C18B115.2 (13)C23—C24—C25120.5 (3)
C2B—C1B—N1B132.0 (17)C23—C24—H24A119.8
C2B—C1B—C6B110.3 (15)C25—C24—H24A119.8
N1B—C1B—C6B117.7 (15)C26—C25—C24117.8 (3)
C3B—C2B—C1B139.7 (18)C26—C25—H25A121.1
C3B—C2B—H2BA110.1C24—C25—H25A121.1
C1B—C2B—H2BA110.1C25—C26—F1118.2 (3)
C2B—C3B—C4B110.3 (17)C25—C26—C27123.6 (3)
C2B—C3B—H3BA124.8F1—C26—C27118.2 (3)
C4B—C3B—H3BA124.8C28—C27—C26118.3 (3)
C5B—C4B—C3B119.2 (18)C28—C27—H27A120.9
C5B—C4B—H4BA120.4C26—C27—H27A120.9
C3B—C4B—H4BA120.4C27—C28—C23120.6 (3)
C4B—C5B—C6B123.7 (18)C27—C28—H28A119.7
C4B—C5B—H5BA118.1C23—C28—H28A119.7
C6B—C5B—H5BA118.1H1W1—O1W—H2W1112.6
C7B—C6B—C5B122.4 (18)
C9A—N1A—C1A—C2A−174.4 (9)C3B—C4B—C5B—C6B−3 (5)
C22A—N1A—C1A—C2A4.2 (11)C4B—C5B—C6B—C7B−171 (4)
C9A—N1A—C1A—C6A2.9 (14)C4B—C5B—C6B—C1B−4 (6)
C22A—N1A—C1A—C6A−178.4 (8)C2B—C1B—C6B—C7B174 (4)
N1A—C1A—C2A—C3A179.9 (7)N1B—C1B—C6B—C7B−8 (6)
C6A—C1A—C2A—C3A2.6 (8)C2B—C1B—C6B—C5B7 (4)
C1A—C2A—C3A—C4A−0.8 (8)N1B—C1B—C6B—C5B−175 (4)
C2A—C3A—C4A—C5A−1.3 (10)C5B—C6B—C7B—C8B179 (4)
C3A—C4A—C5A—C6A1.3 (11)C1B—C6B—C7B—C8B13 (6)
C2A—C1A—C6A—C7A178.2 (8)C6B—C7B—C8B—C9B−5 (6)
N1A—C1A—C6A—C7A0.8 (13)C1B—N1B—C9B—C8B13 (7)
C2A—C1A—C6A—C5A−2.6 (12)C22B—N1B—C9B—C8B−171 (4)
N1A—C1A—C6A—C5A−180.0 (9)C1B—N1B—C9B—C10B−179 (4)
C4A—C5A—C6A—C7A179.7 (9)C22B—N1B—C9B—C10B−3 (7)
C4A—C5A—C6A—C1A0.6 (13)C7B—C8B—C9B—N1B−8 (7)
C1A—C6A—C7A—C8A−2.4 (16)C7B—C8B—C9B—C10B−176 (4)
C5A—C6A—C7A—C8A178.4 (10)N1B—C9B—C10B—C11B−171 (4)
C6A—C7A—C8A—C9A0.5 (16)C8B—C9B—C10B—C11B−4 (7)
C1A—N1A—C9A—C8A−4.8 (17)C9B—C10B—C11B—C12B−178 (4)
C22A—N1A—C9A—C8A176.6 (10)C10B—C11B—C12B—C17B−13 (7)
C1A—N1A—C9A—C10A175.2 (10)C10B—C11B—C12B—C13B−174 (4)
C22A—N1A—C9A—C10A−3.4 (17)C17B—C12B—C13B—C14B7 (6)
C7A—C8A—C9A—N1A3.1 (17)C11B—C12B—C13B—C14B169 (3)
C7A—C8A—C9A—C10A−177.0 (10)C12B—C13B—C14B—C15B4 (4)
N1A—C9A—C10A—C11A−175.9 (11)C20B—N2B—C15B—C16B−171.0 (17)
C8A—C9A—C10A—C11A4.1 (18)C18B—N2B—C15B—C16B−2 (3)
C9A—C10A—C11A—C12A174.7 (11)C20B—N2B—C15B—C14B0 (2)
C10A—C11A—C12A—C17A2.7 (17)C18B—N2B—C15B—C14B169.3 (17)
C10A—C11A—C12A—C13A178.3 (10)C13B—C14B—C15B—N2B179.4 (19)
C17A—C12A—C13A—C14A−0.4 (13)C13B—C14B—C15B—C16B−9 (3)
C11A—C12A—C13A—C14A−176.4 (8)N2B—C15B—C16B—C17B175 (2)
C12A—C13A—C14A—C15A1.5 (10)C14B—C15B—C16B—C17B3 (3)
C18A—N2A—C15A—C16A−7.2 (7)C15B—C16B—C17B—C12B7 (4)
C20A—N2A—C15A—C16A179.8 (5)C13B—C12B—C17B—C16B−12 (6)
C18A—N2A—C15A—C14A175.7 (5)C11B—C12B—C17B—C16B−173 (3)
C20A—N2A—C15A—C14A2.6 (7)C15B—N2B—C18B—C19B95 (2)
C13A—C14A—C15A—N2A173.8 (5)C20B—N2B—C18B—C19B−95 (2)
C13A—C14A—C15A—C16A−3.5 (8)C15B—N2B—C20B—C21B−82 (2)
N2A—C15A—C16A—C17A−172.5 (5)C18B—N2B—C20B—C21B108 (2)
C14A—C15A—C16A—C17A4.8 (8)O3—S1—C23—C24−89.9 (2)
C15A—C16A—C17A—C12A−4.1 (11)O1—S1—C23—C24149.0 (2)
C13A—C12A—C17A—C16A1.7 (13)O2—S1—C23—C2431.6 (3)
C11A—C12A—C17A—C16A177.4 (8)O3—S1—C23—C2887.8 (3)
C15A—N2A—C18A—C19A−78.4 (6)O1—S1—C23—C28−33.3 (3)
C20A—N2A—C18A—C19A95.0 (5)O2—S1—C23—C28−150.7 (2)
C15A—N2A—C20A—C21A78.1 (6)C28—C23—C24—C250.2 (4)
C18A—N2A—C20A—C21A−95.3 (5)S1—C23—C24—C25178.0 (2)
C9B—N1B—C1B—C2B172 (3)C23—C24—C25—C26−0.2 (4)
C22B—N1B—C1B—C2B−3 (5)C24—C25—C26—F1−179.2 (2)
C9B—N1B—C1B—C6B−6 (6)C24—C25—C26—C27−0.2 (5)
C22B—N1B—C1B—C6B179 (3)C25—C26—C27—C280.6 (5)
N1B—C1B—C2B—C3B179 (3)F1—C26—C27—C28179.5 (3)
C6B—C1B—C2B—C3B−3 (2)C26—C27—C28—C23−0.5 (5)
C1B—C2B—C3B—C4B−4.1 (16)C24—C23—C28—C270.1 (4)
C2B—C3B—C4B—C5B6 (3)S1—C23—C28—C27−177.7 (3)
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O10.941.952.872 (4)168
O1W—H2W1···O2i0.902.092.909 (4)151
C20A—H20B···F1ii0.972.503.471 (6)179
C25—H25A···O1Wiii0.932.433.341 (4)167
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O1W—H1W1⋯O10.941.952.872 (4)168
O1W—H2W1⋯O2i 0.902.092.909 (4)151
C20A—H20B⋯F1ii 0.972.503.471 (6)179
C25—H25A⋯O1W iii 0.932.433.341 (4)167

Symmetry codes: (i) ; (ii) ; (iii) .

  8 in total

1.  Antibacterial activities of some bisisoquinolinium salts.

Authors:  H O COLLIER; M D POTTER; E P TAYLOR
Journal:  Br J Pharmacol Chemother       Date:  1953-03

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Anti-bacterial activity of synthetic N-heterocyclic oxidizing compounds.

Authors:  G O Babalola
Journal:  Lett Appl Microbiol       Date:  1998-01       Impact factor: 2.858

4.  Synthesis, structure and in vitro antibacterial activities of new hybrid disinfectants quaternary ammonium compounds: pyridinium and quinolinium stilbene benzenesulfonates.

Authors:  Kullapa Chanawanno; Suchada Chantrapromma; Theerasak Anantapong; Akkharawit Kanjana-Opas; Hoong-Kun Fun
Journal:  Eur J Med Chem       Date:  2010-06-17       Impact factor: 6.514

5.  2-[(E)-2-(4-Ethoxy-phen-yl)ethen-yl]-1-methyl-quinolinium iodide dihydrate.

Authors:  Hoong-Kun Fun; Kullapa Chanawanno; Thawanrat Kobkeatthawin; Suchada Chantrapromma
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-27

6.  2-[(E)-4-(Diethyl-amino)-styr-yl]-1-methyl-pyridinium iodide.

Authors:  Narissara Kaewmanee; Kullapa Chanawanno; Suchada Chantrapromma; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-25

7.  (E)-2-[4-(Diethyl-amino)-styr-yl]-1-methyl-pyridinium benzene-sulfonate mono-hydrate.

Authors:  Hoong-Kun Fun; Narissara Kaewmanee; Kullapa Chanawanno; Suchada Chantrapromma
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-02-09

8.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  8 in total
  1 in total

1.  (E)-2-[4-(Di-ethyl-amino)-styr-yl]-1-methyl-quinolin-1-ium 4-chloro-benzene-sulfonate monohydrate.

Authors:  Suchada Chantrapromma; Narissara Kaewmanee; Nawong Boonnak; Ching Kheng Quah; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-03-05
  1 in total

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