Literature DB >> 21581874

Bis{4-[(E)-2-(1H-indol-3-yl)ethen-yl]-1-methyl-pyridinium} 4-fluoro-benzene-sulfonate nitrate 0.25-hydrate.

Suchada Chantrapromma, Hoong-Kun Fun.   

Abstract

In the title compound, 2C(16)H(15)N(2) (+)·C(6)H(4)FO(3)S(-)·NO(3) (-)·0.25H(2)O, the two cations are nearly planar, with dihedral angles of 1.34 (14) and 4.6 (2)°, respectively, between the pyridinium and indole rings. The cations each adopt E configurations with respect to the C=C bonds and are inclined to each other with a dihedral angle of 77.66 (5)°. The ethenyl group of one cation is disordered over two sites with occupancies of 0.685 (12) and 0.315 (12), and the sulfonate group of the 4-fluoro-benzene-sulfonate anion is also disordered with occupancies of 0.535 (10) and 0.465 (10) for the two sets of O atoms. The anion is also inclined to the two cations, with dihedral angles between the mean planes of the benzene ring and the π-conjugated systems of the cations of 24.72 (11) and 79.83 (11)°. In the crystal structure, the cations are stacked in an anti-parallel fashion into columns approximately along the a axis and are further linked through the anions into a three-dimensional network via N-H⋯O and C-H⋯O inter-actions. The water mol-ecule forms O-H⋯O hydrogen bonds to the nitrate anion and C-H⋯π inter-actions are also observed.

Entities:  

Year:  2009        PMID： 21581874      PMCID： PMC2968363          DOI： 10.1107/S1600536809000026

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


Related literature

For details of nonlinear optical materials, see, for example: Dittrich et al. (2003 ▶); Nogi et al. (2000 ▶); Oudar & LePerson (1975 ▶); Sato et al. (1999 ▶). For related structures, see, for example: Chantrapromma et al. (2006 ▶, 2007 ▶, 2008 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

2C16H15N2 +·C6H4FO3S−·NO3 −·0.25H2O M = 712.27 Triclinic, a = 8.7750 (6) Å b = 13.6366 (1) Å c = 15.3190 (11) Å α = 97.520 (1)° β = 91.236 (1)° γ = 99.861 (1)° V = 1788.66 (18) Å3 Z = 2 Mo Kα radiation μ = 0.15 mm−1 T = 297 (2) K 0.57 × 0.39 × 0.12 mm

Data collection

Siemens SMART CCD area-detector diffractometer Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996 ▶) T min = 0.919, T max = 0.982 17243 measured reflections 6287 independent reflections 4818 reflections with I > 2σ(I) R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.063 wR(F 2) = 0.199 S = 1.03 6287 reflections 520 parameters H-atom parameters constrained Δρmax = 0.46 e Å−3 Δρmin = −0.25 e Å−3 Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000026/sj2569sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000026/sj2569Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
2C16H15N2+·C6H4FO3S−·NO3−·0.25H2OZ = 2
Mr = 712.27F(000) = 745
Triclinic, P1Dx = 1.322 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7750 (6) ÅCell parameters from 6287 reflections
b = 13.6366 (1) Åθ = 1.3–25.0°
c = 15.3190 (11) ŵ = 0.15 mm−1
α = 97.520 (1)°T = 297 K
β = 91.236 (1)°Plate, orange
γ = 99.861 (1)°0.57 × 0.39 × 0.12 mm
V = 1788.66 (18) Å3
Siemens SMART CCD area-detector diffractometer6287 independent reflections
Radiation source: fine-focus sealed tube4818 reflections with I > 2σ(I)
graphiteRint = 0.018
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 1.3°
ω scansh = −10→10
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)k = −16→16
Tmin = 0.919, Tmax = 0.982l = −18→18
17243 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.1048P)2 + 0.7458P] where P = (Fo2 + 2Fc2)/3
6287 reflections(Δ/σ)max < 0.001
520 parametersΔρmax = 0.46 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
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.
xyzUiso*/UeqOcc. (<1)
F10.8301 (3)0.53738 (13)0.13528 (13)0.1070 (7)
S10.74535 (14)0.96215 (6)0.30690 (6)0.0943 (4)
O1A0.7947 (14)0.9676 (5)0.3874 (4)0.128 (4)0.535 (10)
O2A0.5540 (7)0.9537 (4)0.3014 (6)0.122 (3)0.535 (10)
O3A0.7858 (15)1.0287 (7)0.2507 (7)0.117 (4)0.535 (10)
O1B0.6669 (17)0.9575 (5)0.3770 (7)0.148 (7)0.465 (10)
O2B0.7404 (16)1.0297 (9)0.2476 (7)0.106 (4)0.465 (10)
O3B0.9324 (9)1.0071 (5)0.3454 (6)0.123 (3)0.465 (10)
O40.7248 (4)0.3823 (2)0.8149 (2)0.1299 (11)
O50.7224 (8)0.3889 (4)0.9475 (3)0.241 (3)
O60.6872 (4)0.2501 (2)0.8724 (3)0.1355 (12)
N11.1622 (3)0.86382 (16)0.41062 (15)0.0630 (6)
N20.7682 (3)0.22728 (16)0.34872 (16)0.0698 (6)
H1N20.76860.16770.32230.084*
N30.4743 (3)1.1617 (2)1.09022 (17)0.0769 (7)
N4−0.1419 (3)0.6053 (2)0.88513 (19)0.0872 (8)
H1N4−0.17240.54310.89040.105*
N50.7084 (3)0.3399 (2)0.8801 (2)0.0836 (7)
C10.7643 (3)0.84191 (19)0.25284 (17)0.0626 (7)
C20.9019 (4)0.8268 (2)0.21795 (19)0.0722 (8)
H2A0.98350.88060.21950.087*
C30.9200 (4)0.7333 (3)0.1809 (2)0.0806 (9)
H3A1.01390.72390.15710.097*
C40.8020 (4)0.6533 (2)0.1782 (2)0.0771 (8)
C50.6630 (4)0.6681 (2)0.2113 (2)0.0877 (10)
H5A0.58140.61420.20890.105*
C60.6433 (4)0.7629 (2)0.2484 (2)0.0800 (9)
H6A0.54830.77310.27030.096*
C71.1090 (3)0.6898 (2)0.36194 (18)0.0651 (7)
H7A1.13160.63500.32480.078*
C81.1910 (3)0.7838 (2)0.35711 (19)0.0686 (7)
H8A1.26740.79220.31630.082*
C91.0525 (3)0.8512 (2)0.46932 (19)0.0674 (7)
H9A1.03340.90670.50680.081*
C100.9685 (3)0.75962 (19)0.47560 (19)0.0646 (7)
H10A0.89300.75360.51720.078*
C110.9924 (3)0.67502 (18)0.42152 (16)0.0547 (6)
C120.9001 (3)0.57771 (19)0.42901 (17)0.0595 (6)
H12A0.82480.57540.47080.071*
C130.9144 (3)0.49223 (19)0.38127 (18)0.0618 (6)
H13A0.98930.49680.33930.074*
C140.8305 (3)0.39367 (18)0.38538 (17)0.0577 (6)
C150.8606 (4)0.3107 (2)0.33221 (19)0.0696 (7)
H15A0.93560.31240.29020.084*
C160.6722 (3)0.25210 (18)0.41484 (18)0.0584 (6)
C170.5603 (3)0.1904 (2)0.4537 (2)0.0702 (8)
H17A0.54000.12130.43630.084*
C180.4800 (3)0.2348 (2)0.5189 (2)0.0785 (9)
H18A0.40330.19520.54610.094*
C190.5115 (3)0.3387 (2)0.5452 (2)0.0762 (8)
H19A0.45500.36690.58940.091*
C200.6248 (3)0.3999 (2)0.50683 (18)0.0626 (7)
H20A0.64550.46880.52520.075*
C210.7077 (3)0.35702 (17)0.44012 (16)0.0529 (6)
C221.2493 (5)0.9649 (2)0.4041 (3)0.0987 (11)
H22A1.27231.00150.46220.148*
H22B1.18811.00000.37050.148*
H22C1.34410.95910.37540.148*
C230.3467 (6)0.9948 (3)1.0839 (4)0.1117 (15)
H23A0.33360.93471.10750.134*
C240.4531 (5)1.0744 (3)1.1227 (2)0.0925 (10)
H24A0.51141.06771.17230.111*
C250.3890 (4)1.1693 (3)1.0182 (2)0.0797 (8)
H25A0.40301.22970.99500.096*
C260.2841 (4)1.0915 (3)0.9792 (2)0.0863 (10)
H26A0.22781.09980.92930.104*
C270.2572 (4)1.0021 (3)1.0093 (3)0.0964 (11)
C28A0.1315 (7)0.9283 (6)0.9502 (4)0.077 (2)0.685 (12)
H28A0.08480.94990.90280.093*0.685 (12)
C29A0.0901 (6)0.8359 (5)0.9661 (4)0.075 (2)0.685 (12)
H29A0.13470.81761.01580.090*0.685 (12)
C28B0.1802 (10)0.8954 (7)1.0036 (6)0.052 (3)0.315 (12)
H28B0.19800.85051.04190.062*0.315 (12)
C29B0.0751 (16)0.8741 (10)0.9296 (8)0.057 (3)0.315 (12)
H29B0.06110.92180.89330.068*0.315 (12)
C30−0.0168 (4)0.7624 (3)0.9137 (2)0.0847 (10)
C31−0.0391 (4)0.6689 (3)0.9388 (2)0.0946 (10)
H31A0.01110.65200.98730.114*
C32−0.1923 (3)0.6535 (2)0.81984 (19)0.0657 (7)
C33−0.2938 (3)0.6159 (2)0.7491 (2)0.0756 (8)
H33A−0.34210.54890.74020.091*
C34−0.3209 (4)0.6814 (3)0.6919 (2)0.0849 (9)
H34A−0.38870.65840.64320.102*
C35−0.2491 (4)0.7807 (3)0.7056 (2)0.0885 (10)
H35A−0.27020.82340.66600.106*
C36−0.1480 (4)0.8182 (2)0.7758 (2)0.0803 (9)
H36A−0.10040.88530.78400.096*
C37−0.1175 (3)0.7536 (2)0.83492 (19)0.0661 (7)
C380.5860 (4)1.2495 (3)1.1315 (3)0.1201 (15)
H38A0.61531.29391.08870.180*
H38B0.67611.22761.15320.180*
H38C0.53931.28421.17950.180*
O1W0.4653 (13)0.4288 (9)0.0301 (9)0.128 (4)0.25
H1W10.55290.46190.05000.192*0.25
H2W10.43510.4572−0.01160.192*0.25
U11U22U33U12U13U23
F10.168 (2)0.0544 (10)0.1004 (14)0.0473 (11)0.0094 (13)−0.0183 (9)
S10.1704 (10)0.0472 (4)0.0706 (5)0.0300 (5)0.0304 (6)0.0093 (3)
O1A0.230 (11)0.084 (4)0.065 (4)0.053 (7)−0.043 (6)−0.029 (3)
O2A0.100 (4)0.093 (4)0.177 (7)0.043 (3)0.034 (4)−0.013 (4)
O3A0.190 (9)0.040 (3)0.126 (7)0.019 (4)0.081 (6)0.027 (4)
O1B0.252 (14)0.067 (4)0.139 (10)0.049 (7)0.138 (11)0.020 (5)
O2B0.168 (8)0.079 (5)0.078 (5)0.062 (5)−0.045 (6)−0.007 (4)
O3B0.114 (5)0.083 (4)0.153 (6)0.002 (4)−0.037 (5)−0.029 (4)
O40.135 (2)0.110 (2)0.156 (3)0.0253 (18)0.055 (2)0.045 (2)
O50.396 (8)0.236 (5)0.098 (3)0.138 (5)−0.060 (4)−0.045 (3)
O60.124 (2)0.086 (2)0.203 (3)0.0166 (17)−0.014 (2)0.050 (2)
N10.0650 (13)0.0505 (12)0.0690 (14)−0.0022 (10)−0.0069 (11)0.0094 (10)
N20.0892 (16)0.0444 (12)0.0731 (15)0.0114 (11)0.0006 (13)−0.0007 (10)
N30.0627 (14)0.0909 (19)0.0725 (15)0.0172 (13)0.0045 (12)−0.0102 (14)
N40.0919 (19)0.0847 (18)0.0885 (18)0.0187 (15)−0.0002 (15)0.0213 (15)
N50.0857 (18)0.087 (2)0.0799 (19)0.0249 (15)−0.0081 (14)0.0076 (16)
C10.0860 (19)0.0502 (14)0.0534 (14)0.0155 (13)0.0096 (13)0.0077 (11)
C20.0700 (18)0.0675 (18)0.0755 (18)0.0049 (14)0.0007 (14)0.0067 (14)
C30.0766 (19)0.088 (2)0.081 (2)0.0330 (18)0.0066 (16)0.0031 (17)
C40.103 (2)0.0663 (18)0.0633 (17)0.0322 (17)−0.0080 (16)−0.0074 (14)
C50.090 (2)0.0594 (18)0.103 (2)−0.0051 (16)0.0003 (19)−0.0035 (16)
C60.0766 (19)0.0626 (18)0.100 (2)0.0125 (15)0.0224 (17)0.0054 (16)
C70.0765 (17)0.0536 (15)0.0646 (16)0.0145 (13)−0.0014 (13)0.0022 (12)
C80.0648 (16)0.0740 (18)0.0664 (17)0.0049 (14)0.0057 (13)0.0167 (14)
C90.0754 (18)0.0527 (15)0.0713 (17)0.0084 (13)0.0003 (14)0.0022 (13)
C100.0665 (16)0.0540 (15)0.0731 (17)0.0088 (12)0.0069 (13)0.0093 (13)
C110.0557 (14)0.0518 (13)0.0574 (14)0.0090 (11)−0.0035 (11)0.0118 (11)
C120.0600 (14)0.0564 (15)0.0632 (15)0.0117 (12)0.0060 (12)0.0092 (12)
C130.0671 (16)0.0531 (14)0.0650 (16)0.0083 (12)0.0042 (12)0.0101 (12)
C140.0625 (15)0.0491 (13)0.0623 (15)0.0114 (11)0.0002 (12)0.0088 (11)
C150.0844 (19)0.0546 (15)0.0704 (17)0.0140 (14)0.0131 (14)0.0063 (13)
C160.0588 (14)0.0470 (13)0.0687 (16)0.0062 (11)−0.0120 (12)0.0118 (11)
C170.0646 (16)0.0535 (15)0.090 (2)0.0000 (13)−0.0104 (15)0.0178 (14)
C180.0594 (16)0.078 (2)0.099 (2)−0.0031 (14)0.0003 (16)0.0362 (18)
C190.0650 (17)0.083 (2)0.085 (2)0.0186 (15)0.0117 (15)0.0205 (16)
C200.0607 (15)0.0543 (14)0.0749 (17)0.0139 (12)0.0018 (13)0.0114 (13)
C210.0534 (13)0.0437 (12)0.0616 (14)0.0092 (10)−0.0073 (11)0.0080 (10)
C220.111 (3)0.0634 (19)0.108 (3)−0.0272 (18)−0.002 (2)0.0177 (18)
C230.123 (3)0.077 (2)0.151 (4)0.038 (2)0.073 (3)0.034 (3)
C240.100 (3)0.112 (3)0.081 (2)0.050 (2)0.0186 (19)0.025 (2)
C250.081 (2)0.080 (2)0.081 (2)0.0189 (16)0.0132 (17)0.0112 (16)
C260.0677 (19)0.104 (3)0.080 (2)0.0116 (18)−0.0010 (16)−0.0069 (19)
C270.076 (2)0.088 (3)0.118 (3)0.0099 (19)0.033 (2)−0.014 (2)
C28A0.085 (4)0.074 (4)0.076 (4)0.023 (3)0.010 (3)0.006 (3)
C29A0.075 (4)0.086 (4)0.066 (3)0.027 (3)0.007 (3)0.003 (3)
C28B0.056 (6)0.052 (5)0.050 (5)0.011 (4)−0.001 (4)0.014 (4)
C29B0.084 (8)0.055 (7)0.045 (6)0.033 (6)0.016 (5)0.025 (5)
C300.0618 (18)0.099 (3)0.084 (2)0.0144 (17)0.0064 (16)−0.0212 (19)
C310.094 (2)0.110 (3)0.081 (2)0.032 (2)−0.0093 (19)0.002 (2)
C320.0613 (15)0.0689 (17)0.0699 (17)0.0166 (13)0.0105 (13)0.0125 (14)
C330.0676 (17)0.0706 (18)0.086 (2)0.0096 (14)0.0013 (15)0.0058 (16)
C340.082 (2)0.096 (2)0.078 (2)0.0226 (18)−0.0103 (16)0.0067 (18)
C350.106 (3)0.076 (2)0.091 (2)0.0263 (19)0.007 (2)0.0215 (18)
C360.081 (2)0.0619 (17)0.097 (2)0.0138 (15)0.0205 (18)0.0027 (16)
C370.0591 (15)0.0723 (18)0.0669 (16)0.0160 (13)0.0166 (13)0.0017 (14)
C380.083 (2)0.132 (3)0.124 (3)0.006 (2)0.000 (2)−0.044 (3)
O1W0.091 (7)0.134 (10)0.159 (11)0.018 (7)0.018 (7)0.022 (8)
F1—C41.692 (3)C16—C171.378 (4)
S1—O1A1.287 (6)C16—C211.411 (3)
S1—O1B1.291 (6)C17—C181.371 (4)
S1—O3A1.340 (8)C17—H17A0.9300
S1—O2B1.381 (11)C18—C191.398 (4)
S1—O2A1.662 (6)C18—H18A0.9300
S1—O3B1.714 (7)C19—C201.378 (4)
S1—C11.774 (3)C19—H19A0.9300
O4—N51.217 (4)C20—C211.392 (4)
O5—N51.145 (4)C20—H20A0.9300
O6—N51.197 (4)C22—H22A0.9600
N1—C91.336 (4)C22—H22B0.9600
N1—C81.340 (4)C22—H22C0.9600
N1—C221.474 (3)C23—C241.365 (6)
N2—C151.336 (4)C23—C271.396 (6)
N2—C161.376 (4)C23—H23A0.9300
N2—H1N20.8600C24—H24A0.9300
N3—C241.336 (5)C25—C261.345 (5)
N3—C251.344 (4)C25—H25A0.9300
N3—C381.471 (4)C26—C271.345 (5)
N4—C311.324 (4)C26—H26A0.9300
N4—C321.371 (4)C27—C28B1.487 (10)
N4—H1N40.8600C27—C28A1.546 (8)
C1—C21.368 (4)C28A—C29A1.306 (12)
C1—C61.370 (4)C28A—H28A0.9300
C2—C31.363 (4)C29A—C301.402 (7)
C2—H2A0.9300C29A—H29A0.9300
C3—C41.365 (5)C28B—C29B1.41 (2)
C3—H3A0.9300C28B—H28B0.9300
C4—C51.367 (5)C29B—C301.583 (15)
C5—C61.383 (4)C29B—H29B0.9300
C5—H5A0.9300C30—C311.364 (5)
C6—H6A0.9300C30—C371.459 (4)
C7—C81.370 (4)C31—H31A0.9300
C7—C111.392 (4)C32—C331.374 (4)
C7—H7A0.9300C32—C371.397 (4)
C8—H8A0.9300C33—C341.376 (4)
C9—C101.353 (4)C33—H33A0.9300
C9—H9A0.9300C34—C351.379 (5)
C10—C111.379 (4)C34—H34A0.9300
C10—H10A0.9300C35—C361.364 (5)
C11—C121.451 (3)C35—H35A0.9300
C12—C131.319 (4)C36—C371.396 (4)
C12—H12A0.9300C36—H36A0.9300
C13—C141.428 (4)C38—H38A0.9600
C13—H13A0.9300C38—H38B0.9600
C14—C151.373 (4)C38—H38C0.9600
C14—C211.441 (4)O1W—H1W10.8500
C15—H15A0.9300O1W—H2W10.8500
O1A—S1—O1B51.1 (5)C18—C17—C16117.4 (3)
O1A—S1—O3A127.5 (7)C18—C17—H17A121.3
O1B—S1—O3A137.3 (6)C16—C17—H17A121.3
O1A—S1—O2B135.5 (6)C17—C18—C19121.1 (3)
O1B—S1—O2B125.9 (7)C17—C18—H18A119.4
O1A—S1—O2A110.4 (6)C19—C18—H18A119.4
O1B—S1—O2A59.4 (6)C20—C19—C18121.2 (3)
O3A—S1—O2A100.2 (6)C20—C19—H19A119.4
O2B—S1—O2A83.2 (6)C18—C19—H19A119.4
O1A—S1—O3B55.1 (5)C19—C20—C21119.0 (3)
O1B—S1—O3B104.6 (7)C19—C20—H20A120.5
O3A—S1—O3B80.9 (6)C21—C20—H20A120.5
O2B—S1—O3B96.4 (6)C20—C21—C16118.3 (2)
O2A—S1—O3B157.3 (3)C20—C21—C14135.6 (2)
O1A—S1—C1107.2 (3)C16—C21—C14106.1 (2)
O1B—S1—C1112.7 (3)N1—C22—H22A109.5
O3A—S1—C1107.6 (5)N1—C22—H22B109.5
O2B—S1—C1111.5 (5)H22A—C22—H22B109.5
O2A—S1—C1100.7 (2)N1—C22—H22C109.5
O3B—S1—C1100.5 (2)H22A—C22—H22C109.5
C9—N1—C8119.3 (2)H22B—C22—H22C109.5
C9—N1—C22120.3 (3)C24—C23—C27121.2 (4)
C8—N1—C22120.4 (3)C24—C23—H23A119.4
C15—N2—C16109.0 (2)C27—C23—H23A119.4
C15—N2—H1N2125.5N3—C24—C23120.7 (4)
C16—N2—H1N2125.5N3—C24—H24A119.6
C24—N3—C25118.5 (3)C23—C24—H24A119.6
C24—N3—C38122.0 (4)N3—C25—C26121.5 (3)
C25—N3—C38119.5 (3)N3—C25—H25A119.3
C31—N4—C32109.9 (3)C26—C25—H25A119.3
C31—N4—H1N4125.0C27—C26—C25122.6 (4)
C32—N4—H1N4125.0C27—C26—H26A118.7
O5—N5—O6122.5 (5)C25—C26—H26A118.7
O5—N5—O4117.6 (5)C26—C27—C23115.6 (4)
O6—N5—O4119.8 (4)C26—C27—C28B152.5 (6)
C2—C1—C6119.6 (3)C23—C27—C28B91.9 (5)
C2—C1—S1120.0 (2)C26—C27—C28A110.3 (5)
C6—C1—S1120.3 (2)C23—C27—C28A134.2 (5)
C3—C2—C1120.3 (3)C29A—C28A—C27120.6 (6)
C3—C2—H2A119.9C29A—C28A—H28A119.7
C1—C2—H2A119.9C27—C28A—H28A119.7
C2—C3—C4120.8 (3)C28A—C29A—C30124.6 (7)
C2—C3—H3A119.6C28A—C29A—H29A117.7
C4—C3—H3A119.6C30—C29A—H29A117.7
C3—C4—C5119.3 (3)C29B—C28B—C27107.8 (9)
C3—C4—F1119.7 (3)C29B—C28B—H28B126.1
C5—C4—F1120.9 (3)C27—C28B—H28B126.1
C4—C5—C6120.2 (3)C28B—C29B—C30114.3 (10)
C4—C5—H5A119.9C28B—C29B—H29B122.8
C6—C5—H5A119.9C30—C29B—H29B122.8
C1—C6—C5119.7 (3)C31—C30—C29A115.9 (5)
C1—C6—H6A120.1C31—C30—C37105.4 (3)
C5—C6—H6A120.1C29A—C30—C37138.7 (5)
C8—C7—C11121.0 (3)C31—C30—C29B147.6 (6)
C8—C7—H7A119.5C37—C30—C29B106.9 (6)
C11—C7—H7A119.5N4—C31—C30111.1 (3)
N1—C8—C7120.7 (3)N4—C31—H31A124.5
N1—C8—H8A119.7C30—C31—H31A124.5
C7—C8—H8A119.7N4—C32—C33129.5 (3)
N1—C9—C10121.7 (3)N4—C32—C37107.6 (3)
N1—C9—H9A119.2C33—C32—C37122.8 (3)
C10—C9—H9A119.2C32—C33—C34117.2 (3)
C9—C10—C11121.3 (3)C32—C33—H33A121.4
C9—C10—H10A119.3C34—C33—H33A121.4
C11—C10—H10A119.3C33—C34—C35121.0 (3)
C10—C11—C7115.9 (2)C33—C34—H34A119.5
C10—C11—C12120.4 (2)C35—C34—H34A119.5
C7—C11—C12123.7 (2)C36—C35—C34121.9 (3)
C13—C12—C11125.3 (3)C36—C35—H35A119.1
C13—C12—H12A117.4C34—C35—H35A119.1
C11—C12—H12A117.4C35—C36—C37118.6 (3)
C12—C13—C14128.8 (3)C35—C36—H36A120.7
C12—C13—H13A115.6C37—C36—H36A120.7
C14—C13—H13A115.6C36—C37—C32118.5 (3)
C15—C14—C13122.2 (3)C36—C37—C30135.4 (3)
C15—C14—C21105.9 (2)C32—C37—C30106.0 (3)
C13—C14—C21131.9 (2)N3—C38—H38A109.5
N2—C15—C14111.1 (3)N3—C38—H38B109.5
N2—C15—H15A124.4H38A—C38—H38B109.5
C14—C15—H15A124.4N3—C38—H38C109.5
N2—C16—C17129.2 (3)H38A—C38—H38C109.5
N2—C16—C21107.9 (2)H38B—C38—H38C109.5
C17—C16—C21123.0 (3)H1W1—O1W—H2W1107.7
O1A—S1—C1—C2−85.3 (6)C15—C14—C21—C20179.7 (3)
O1B—S1—C1—C2−139.6 (8)C13—C14—C21—C200.6 (5)
O3A—S1—C1—C254.9 (6)C15—C14—C21—C16−0.2 (3)
O2B—S1—C1—C272.4 (7)C13—C14—C21—C16−179.2 (3)
O2A—S1—C1—C2159.3 (4)C25—N3—C24—C23−0.3 (5)
O3B—S1—C1—C2−28.8 (4)C38—N3—C24—C23178.8 (3)
O1A—S1—C1—C692.5 (6)C27—C23—C24—N30.0 (5)
O1B—S1—C1—C638.2 (8)C24—N3—C25—C260.1 (4)
O3A—S1—C1—C6−127.4 (7)C38—N3—C25—C26−179.0 (3)
O2B—S1—C1—C6−109.8 (7)N3—C25—C26—C270.3 (5)
O2A—S1—C1—C6−23.0 (4)C25—C26—C27—C23−0.5 (5)
O3B—S1—C1—C6149.0 (4)C25—C26—C27—C28B−175.9 (8)
C6—C1—C2—C3−1.6 (5)C25—C26—C27—C28A−179.6 (3)
S1—C1—C2—C3176.2 (2)C24—C23—C27—C260.4 (5)
C1—C2—C3—C4−0.3 (5)C24—C23—C27—C28B178.2 (4)
C2—C3—C4—C51.6 (5)C24—C23—C27—C28A179.2 (4)
C2—C3—C4—F1−177.7 (2)C26—C27—C28A—C29A178.2 (4)
C3—C4—C5—C6−1.1 (5)C23—C27—C28A—C29A−0.7 (8)
F1—C4—C5—C6178.2 (3)C28B—C27—C28A—C29A0.7 (5)
C2—C1—C6—C52.1 (5)C27—C28A—C29A—C30−176.6 (4)
S1—C1—C6—C5−175.7 (3)C26—C27—C28B—C29B−3.5 (13)
C4—C5—C6—C1−0.8 (5)C23—C27—C28B—C29B−179.3 (6)
C9—N1—C8—C70.2 (4)C28A—C27—C28B—C29B1.7 (6)
C22—N1—C8—C7−179.1 (3)C27—C28B—C29B—C30179.7 (6)
C11—C7—C8—N10.9 (4)C28A—C29A—C30—C31176.9 (5)
C8—N1—C9—C10−0.7 (4)C28A—C29A—C30—C37−2.4 (8)
C22—N1—C9—C10178.6 (3)C28A—C29A—C30—C29B0.9 (8)
N1—C9—C10—C110.0 (4)C28B—C29B—C30—C31−3.8 (13)
C9—C10—C11—C71.0 (4)C28B—C29B—C30—C29A2.9 (5)
C9—C10—C11—C12−179.6 (2)C28B—C29B—C30—C37−179.3 (6)
C8—C7—C11—C10−1.4 (4)C32—N4—C31—C300.9 (4)
C8—C7—C11—C12179.1 (2)C29A—C30—C31—N4−180.0 (3)
C10—C11—C12—C13−179.4 (3)C37—C30—C31—N4−0.5 (4)
C7—C11—C12—C130.0 (4)C29B—C30—C31—N4−176.0 (7)
C11—C12—C13—C14178.9 (2)C31—N4—C32—C33177.5 (3)
C12—C13—C14—C15−178.6 (3)C31—N4—C32—C37−0.8 (4)
C12—C13—C14—C210.4 (5)N4—C32—C33—C34−178.3 (3)
C16—N2—C15—C14−0.3 (3)C37—C32—C33—C34−0.2 (4)
C13—C14—C15—N2179.5 (2)C32—C33—C34—C35−0.2 (5)
C21—C14—C15—N20.3 (3)C33—C34—C35—C360.4 (5)
C15—N2—C16—C17−179.1 (3)C34—C35—C36—C37−0.1 (5)
C15—N2—C16—C210.2 (3)C35—C36—C37—C32−0.2 (4)
N2—C16—C17—C18−180.0 (3)C35—C36—C37—C30177.6 (3)
C21—C16—C17—C180.8 (4)N4—C32—C37—C36178.9 (3)
C16—C17—C18—C19−0.4 (4)C33—C32—C37—C360.4 (4)
C17—C18—C19—C20−0.3 (5)N4—C32—C37—C300.5 (3)
C18—C19—C20—C210.6 (4)C33—C32—C37—C30−178.0 (3)
C19—C20—C21—C16−0.2 (4)C31—C30—C37—C36−178.0 (3)
C19—C20—C21—C14180.0 (3)C29A—C30—C37—C361.3 (7)
N2—C16—C21—C20−179.9 (2)C29B—C30—C37—C36−0.5 (6)
C17—C16—C21—C20−0.5 (4)C31—C30—C37—C320.0 (3)
N2—C16—C21—C140.0 (3)C29A—C30—C37—C32179.3 (4)
C17—C16—C21—C14179.4 (2)C29B—C30—C37—C32177.5 (4)
D—H···AD—HH···AD···AD—H···A
N2—H1N2···O3Ai0.862.092.950 (10)175
N4—H1N4···O4ii0.862.363.106 (4)145
N4—H1N4···O5ii0.862.433.259 (6)163
O1W—H1W1···O5iii0.852.422.711 (14)101
C6—H6A···O2A0.932.442.866 (7)108
C7—H7A···O4iv0.932.513.224 (4)134
C9—H9A···O1Av0.932.473.169 (8)132
C22—H22A···O1Av0.962.393.256 (8)149
C22—H22C···O2Avi0.962.193.147 (8)175
C23—H23A···O6vii0.932.553.456 (5)164
C15—H15A···Cg1viii0.932.993.896 (3)164
C15—H15A···Cg2viii0.932.723.563 (4)151
C34—H34A···Cg3ix0.932.783.595 (4)147
C38—H38C···Cg2x0.962.953.695 (4)135
Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the rings N4/C30–C32/C37, C32–C37 and C16–C21, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H1N2⋯O3Ai0.862.092.950 (10)175
N4—H1N4⋯O4ii0.862.363.106 (4)145
N4—H1N4⋯O5ii0.862.433.259 (6)163
O1W—H1W1⋯O5iii0.852.422.711 (14)101
C6—H6A⋯O2A0.932.442.866 (7)108
C7—H7A⋯O4iv0.932.513.224 (4)134
C9—H9A⋯O1Av0.932.473.169 (8)132
C22—H22A⋯O1Av0.962.393.256 (8)149
C22—H22C⋯O2Avi0.962.193.147 (8)175
C23—H23A⋯O6vii0.932.553.456 (5)164
C15—H15A⋯Cg1viii0.932.993.896 (3)164
C15—H15A⋯Cg2viii0.932.723.563 (4)151
C34—H34A⋯Cg3ix0.932.783.595 (4)147
C38—H38C⋯Cg2x0.962.953.695 (4)135

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) .

  2 in total

1.  A short history of SHELX.

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

2.  (E)-2-[4-(Dimethyl-amino)styr-yl]-1-methyl-quinolinium iodide sesquihydrate.

Authors:  Suchada Chantrapromma; Thawanrat Kobkeatthawin; Kullapa Chanawanno; Chatchanok Karalai; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-04-18
  2 in total
  1 in total

1.  Bis{4-[(E)-2-(1H-indol-3-yl)ethen-yl]-1-methyl-pyridinium} 4-chloro-benzene-sulfonate nitrate.

Authors:  Hoong-Kun Fun; Ching Kheng Quah; Nawong Boonnak; Suchada Chantrapromma
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-11-09
  1 in total

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