organic compounds
(E)-2-[4-(Dimethylamino)styryl]-1-methylquinolinium 4-methylbenzenesulfonate monohydrate†
aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: suchada.c@psu.ac.th
In the title compound, C20H21N2+·C7H7O3S−·H2O, the cation is essentially planar, as indicated by the dihedral angle of 2.79 (13)° between the quinolinium and the dimethylaminophenyl rings, and exists in the E configuration. The π-conjugated planes of the cation and the anion are inclined to each other at a dihedral angle of 66.95 (12)°. The cation is linked to the anion through C—H⋯O hydrogen bonds and the anion is further linked with the water molecule by O—H⋯O hydrogen bonds, forming a three-molecule unit. These units are arranged in a face-to-face manner into a ribbon-like structure along the b axis. The ribbons are stacked along the c axis. The is further stabilized by C—H⋯π interactions involving the dimethylaminophenyl and methylphenyl rings. A π–π interaction with a centroid–centroid distance of 3.6074 (19) Å is also observed.
Related literature
For bond-length data, see: Allen et al. (1987). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For background to NLO materials research, see: Dittrich et al. (2003); Nogi et al. (2000); Ogawa et al. (2008); Otero et al. (2002); Sato et al. (1999); Weir et al. (2003); Yang et al. (2007). For related structures, see, for example: Adachi et al. (1999); Chantrapromma et al. (2008); Ogawa et al. (2008); Rahman et al. (2003).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); 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).
Supporting information
10.1107/S1600536808040671/is2369sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808040671/is2369Isup2.hkl
(E)-2-[4-(Dimethylamino)styryl]-1-methylpyridinium iodide (compound A) was synthesized according to our previously reported procedure (Chantrapromma et al., 2008). Silver(I) p-toluensulfonate (compound B) was synthesized according to a previous method (Rahman et al., 2003). The title compound was then prepared by mixing compound A (0.20 g, 0.5 mmol) in hot methanol (50 ml) and compound B (0.12 g, 0.5 mmol) in hot methanol (30 ml). The mixture immediately yielded a grey precipitate of silver iodide. After stirring the mixture for 30 min, the precipitate of silver iodide was removed and the resulting solution was evaporated yielding a green solid. Green block-shaped single crystals of the title compound suitable for X-ray
were recrystalized from methanol by slow evaporation of the solvent at room temperature a few weeks (m.p. 557–558 K).All H atoms were placed in calculated positions, with d(O—H) = 0.88–0.90 Å, Uiso(H) = 1.5Ueq(O), d(C—H) = 0.93 Å, Uiso(H) = 1.2Ueq(C) for aromatic and CH, and 0.96 Å, Uiso(H) = 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 0.98 Å from C8 and the deepest hole is located at 0.96 Å from S1.
Data collection: APEX2 (Bruker, 2005); cell
APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2003).Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. | |
Fig. 2. The crystal packing of (I) viewed along the b axis. The O—H···O and weak C—H···O interactions are drawn as dashed lines. |
C20H21N2+·C7H7O3S−·H2O | Z = 2 |
Mr = 478.60 | F(000) = 508 |
Triclinic, P1 | Dx = 1.359 Mg m−3 |
Hall symbol: -P 1 | Melting point = 557–558 K |
a = 10.9739 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1789 (5) Å | Cell parameters from 5390 reflections |
c = 11.1923 (9) Å | θ = 1.2–27.5° |
α = 97.133 (5)° | µ = 0.18 mm−1 |
β = 100.322 (5)° | T = 100 K |
γ = 117.021 (3)° | Block, green |
V = 1169.78 (13) Å3 | 0.24 × 0.19 × 0.08 mm |
Bruker SMART APEX2 CCD area-detector diffractometer | 5390 independent reflections |
Radiation source: fine-focus sealed tube | 3272 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 1.9° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −14→14 |
Tmin = 0.958, Tmax = 0.986 | l = −14→11 |
17557 measured reflections |
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)] = 0.072 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.203 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0951P)2 + 0.1631P] where P = (Fo2 + 2Fc2)/3 |
5390 reflections | (Δ/σ)max < 0.001 |
311 parameters | Δρmax = 0.60 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
C20H21N2+·C7H7O3S−·H2O | γ = 117.021 (3)° |
Mr = 478.60 | V = 1169.78 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.9739 (5) Å | Mo Kα radiation |
b = 11.1789 (5) Å | µ = 0.18 mm−1 |
c = 11.1923 (9) Å | T = 100 K |
α = 97.133 (5)° | 0.24 × 0.19 × 0.08 mm |
β = 100.322 (5)° |
Bruker SMART APEX2 CCD area-detector diffractometer | 5390 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3272 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.986 | Rint = 0.073 |
17557 measured reflections |
R[F2 > 2σ(F2)] = 0.072 | 0 restraints |
wR(F2) = 0.203 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.60 e Å−3 |
5390 reflections | Δρmin = −0.47 e Å−3 |
311 parameters |
Experimental. The low-temparture data was collected with the Oxford Cryosystem Cobra low-temperature attachment. |
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 | ||
S1 | 0.16105 (8) | 0.41169 (9) | 0.37784 (7) | 0.0306 (2) | |
O1 | 0.0863 (2) | 0.4772 (2) | 0.3214 (2) | 0.0361 (6) | |
O2 | 0.2576 (3) | 0.4944 (4) | 0.4973 (2) | 0.0784 (11) | |
O3 | 0.0690 (3) | 0.2712 (3) | 0.3786 (3) | 0.0708 (10) | |
O1W | 0.2135 (2) | 0.6205 (2) | 0.7095 (2) | 0.0371 (6) | |
H1W | 0.2122 | 0.5660 | 0.6424 | 0.056* | |
H2W | 0.1227 | 0.5918 | 0.7009 | 0.056* | |
N1 | 0.7361 (3) | 0.0767 (3) | 0.5500 (2) | 0.0286 (6) | |
N2 | 1.1460 (3) | −0.1954 (3) | 0.0336 (2) | 0.0342 (6) | |
C1 | 0.6510 (3) | 0.0789 (3) | 0.6300 (3) | 0.0270 (7) | |
C2 | 0.6415 (3) | 0.1968 (3) | 0.6702 (3) | 0.0331 (7) | |
H2A | 0.6928 | 0.2775 | 0.6453 | 0.040* | |
C3 | 0.5566 (3) | 0.1928 (3) | 0.7459 (3) | 0.0343 (8) | |
H3A | 0.5517 | 0.2722 | 0.7728 | 0.041* | |
C4 | 0.4776 (3) | 0.0760 (4) | 0.7845 (3) | 0.0335 (8) | |
H4A | 0.4200 | 0.0770 | 0.8359 | 0.040* | |
C5 | 0.4840 (3) | −0.0424 (3) | 0.7467 (3) | 0.0332 (8) | |
H5A | 0.4311 | −0.1218 | 0.7726 | 0.040* | |
C6 | 0.5721 (3) | −0.0429 (3) | 0.6678 (3) | 0.0283 (7) | |
C7 | 0.5835 (3) | −0.1616 (3) | 0.6271 (3) | 0.0333 (7) | |
H7A | 0.5333 | −0.2419 | 0.6529 | 0.040* | |
C8 | 0.6659 (3) | −0.1590 (3) | 0.5517 (3) | 0.0321 (7) | |
H8A | 0.6733 | −0.2375 | 0.5274 | 0.039* | |
C9 | 0.7441 (3) | −0.0373 (3) | 0.5067 (3) | 0.0252 (6) | |
C10 | 0.8232 (3) | −0.0412 (3) | 0.4199 (3) | 0.0281 (7) | |
H10A | 0.8713 | 0.0395 | 0.3939 | 0.034* | |
C11 | 0.8347 (3) | −0.1494 (3) | 0.3726 (3) | 0.0310 (7) | |
H11A | 0.7869 | −0.2295 | 0.3996 | 0.037* | |
C12 | 0.9139 (3) | −0.1564 (3) | 0.2832 (3) | 0.0297 (7) | |
C13 | 0.9132 (3) | −0.2798 (3) | 0.2436 (3) | 0.0335 (7) | |
H13A | 0.8599 | −0.3560 | 0.2733 | 0.040* | |
C14 | 0.9879 (3) | −0.2927 (3) | 0.1630 (3) | 0.0304 (7) | |
H14A | 0.9845 | −0.3772 | 0.1394 | 0.036* | |
C15 | 1.0705 (3) | −0.1817 (3) | 0.1142 (3) | 0.0265 (7) | |
C16 | 1.0722 (3) | −0.0549 (3) | 0.1534 (3) | 0.0296 (7) | |
H16A | 1.1246 | 0.0212 | 0.1232 | 0.035* | |
C17 | 0.9956 (3) | −0.0444 (3) | 0.2368 (3) | 0.0303 (7) | |
H17A | 0.9988 | 0.0396 | 0.2624 | 0.036* | |
C18 | 1.1368 (4) | −0.3274 (4) | −0.0096 (3) | 0.0400 (8) | |
H18A | 1.1633 | −0.3597 | 0.0609 | 0.060* | |
H18B | 1.1998 | −0.3172 | −0.0617 | 0.060* | |
H18C | 1.0412 | −0.3928 | −0.0566 | 0.060* | |
C19 | 1.2199 (4) | −0.0842 (4) | −0.0251 (3) | 0.0456 (9) | |
H19A | 1.2955 | −0.0062 | 0.0374 | 0.068* | |
H19B | 1.1546 | −0.0580 | −0.0667 | 0.068* | |
H19C | 1.2584 | −0.1150 | −0.0849 | 0.068* | |
C20 | 0.8178 (4) | 0.2048 (3) | 0.5119 (3) | 0.0373 (8) | |
H20A | 0.8989 | 0.2051 | 0.4907 | 0.056* | |
H20B | 0.8488 | 0.2828 | 0.5794 | 0.056* | |
H20C | 0.7590 | 0.2104 | 0.4405 | 0.056* | |
C21 | 0.2694 (3) | 0.4028 (3) | 0.2798 (3) | 0.0255 (6) | |
C22 | 0.2061 (3) | 0.3196 (3) | 0.1602 (3) | 0.0333 (7) | |
H22A | 0.1077 | 0.2714 | 0.1305 | 0.040* | |
C23 | 0.2884 (3) | 0.3080 (3) | 0.0850 (3) | 0.0313 (7) | |
H23A | 0.2447 | 0.2519 | 0.0046 | 0.038* | |
C24 | 0.4360 (3) | 0.3785 (3) | 0.1271 (3) | 0.0291 (7) | |
C25 | 0.4974 (3) | 0.4628 (3) | 0.2463 (3) | 0.0300 (7) | |
H25A | 0.5958 | 0.5115 | 0.2759 | 0.036* | |
C26 | 0.4160 (3) | 0.4765 (3) | 0.3227 (3) | 0.0286 (7) | |
H26A | 0.4595 | 0.5349 | 0.4021 | 0.034* | |
C27 | 0.5253 (4) | 0.3608 (4) | 0.0459 (3) | 0.0370 (8) | |
H27A | 0.4763 | 0.3403 | −0.0404 | 0.055* | |
H27B | 0.5420 | 0.2863 | 0.0616 | 0.055* | |
H27C | 0.6143 | 0.4446 | 0.0649 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0328 (4) | 0.0371 (5) | 0.0331 (4) | 0.0226 (4) | 0.0159 (3) | 0.0132 (4) |
O1 | 0.0380 (13) | 0.0384 (13) | 0.0485 (14) | 0.0270 (12) | 0.0196 (11) | 0.0202 (11) |
O2 | 0.0542 (18) | 0.157 (3) | 0.0318 (15) | 0.068 (2) | 0.0054 (13) | −0.0097 (17) |
O3 | 0.095 (2) | 0.0431 (16) | 0.127 (3) | 0.0462 (17) | 0.094 (2) | 0.0523 (17) |
O1W | 0.0345 (12) | 0.0385 (14) | 0.0405 (13) | 0.0194 (11) | 0.0115 (11) | 0.0084 (11) |
N1 | 0.0282 (14) | 0.0278 (14) | 0.0312 (14) | 0.0141 (12) | 0.0091 (11) | 0.0086 (11) |
N2 | 0.0324 (15) | 0.0387 (16) | 0.0352 (15) | 0.0182 (14) | 0.0150 (12) | 0.0091 (13) |
C1 | 0.0221 (15) | 0.0381 (18) | 0.0213 (15) | 0.0142 (14) | 0.0073 (12) | 0.0086 (13) |
C2 | 0.0332 (18) | 0.0310 (18) | 0.0383 (18) | 0.0153 (15) | 0.0120 (15) | 0.0163 (15) |
C3 | 0.0381 (18) | 0.0316 (18) | 0.0392 (19) | 0.0222 (16) | 0.0089 (15) | 0.0096 (15) |
C4 | 0.0285 (17) | 0.044 (2) | 0.0311 (17) | 0.0186 (16) | 0.0121 (14) | 0.0109 (15) |
C5 | 0.0296 (17) | 0.0341 (18) | 0.0315 (17) | 0.0096 (15) | 0.0088 (14) | 0.0161 (14) |
C6 | 0.0322 (17) | 0.0255 (16) | 0.0257 (16) | 0.0167 (14) | −0.0004 (13) | 0.0022 (12) |
C7 | 0.0331 (17) | 0.0292 (18) | 0.0358 (18) | 0.0116 (15) | 0.0110 (15) | 0.0145 (14) |
C8 | 0.0316 (17) | 0.0367 (19) | 0.0280 (16) | 0.0170 (16) | 0.0075 (14) | 0.0070 (14) |
C9 | 0.0240 (15) | 0.0229 (16) | 0.0263 (16) | 0.0122 (13) | 0.0002 (12) | 0.0035 (12) |
C10 | 0.0259 (16) | 0.0324 (18) | 0.0286 (16) | 0.0153 (15) | 0.0085 (13) | 0.0093 (13) |
C11 | 0.0311 (17) | 0.0281 (17) | 0.0328 (17) | 0.0130 (15) | 0.0092 (14) | 0.0084 (14) |
C12 | 0.0270 (16) | 0.0349 (18) | 0.0266 (16) | 0.0157 (15) | 0.0045 (13) | 0.0062 (14) |
C13 | 0.0283 (17) | 0.0358 (19) | 0.0319 (17) | 0.0125 (15) | 0.0066 (14) | 0.0080 (14) |
C14 | 0.0284 (16) | 0.0308 (18) | 0.0344 (17) | 0.0161 (15) | 0.0106 (14) | 0.0065 (14) |
C15 | 0.0231 (15) | 0.0303 (17) | 0.0247 (15) | 0.0135 (14) | 0.0040 (12) | 0.0038 (13) |
C16 | 0.0258 (16) | 0.0288 (17) | 0.0328 (17) | 0.0123 (14) | 0.0058 (13) | 0.0098 (14) |
C17 | 0.0325 (17) | 0.0285 (17) | 0.0297 (17) | 0.0188 (15) | 0.0007 (13) | 0.0008 (13) |
C18 | 0.040 (2) | 0.049 (2) | 0.039 (2) | 0.0293 (19) | 0.0136 (16) | 0.0030 (16) |
C19 | 0.041 (2) | 0.060 (3) | 0.045 (2) | 0.024 (2) | 0.0236 (17) | 0.0249 (19) |
C20 | 0.0404 (19) | 0.0348 (19) | 0.044 (2) | 0.0187 (17) | 0.0220 (16) | 0.0160 (16) |
C21 | 0.0289 (16) | 0.0276 (17) | 0.0267 (15) | 0.0172 (14) | 0.0103 (13) | 0.0113 (13) |
C22 | 0.0266 (16) | 0.043 (2) | 0.0309 (17) | 0.0165 (16) | 0.0082 (14) | 0.0102 (15) |
C23 | 0.0352 (18) | 0.0352 (18) | 0.0227 (16) | 0.0169 (16) | 0.0069 (14) | 0.0065 (13) |
C24 | 0.0361 (17) | 0.0287 (17) | 0.0334 (17) | 0.0207 (15) | 0.0148 (14) | 0.0157 (14) |
C25 | 0.0222 (15) | 0.0281 (17) | 0.0388 (18) | 0.0102 (14) | 0.0078 (13) | 0.0132 (14) |
C26 | 0.0297 (16) | 0.0240 (16) | 0.0303 (16) | 0.0115 (14) | 0.0086 (13) | 0.0063 (13) |
C27 | 0.0410 (19) | 0.045 (2) | 0.042 (2) | 0.0286 (18) | 0.0240 (16) | 0.0208 (16) |
S1—O3 | 1.433 (3) | C12—C17 | 1.396 (4) |
S1—O2 | 1.435 (3) | C13—C14 | 1.359 (4) |
S1—O1 | 1.443 (2) | C13—H13A | 0.9300 |
S1—C21 | 1.782 (3) | C14—C15 | 1.408 (4) |
O1W—H1W | 0.8997 | C14—H14A | 0.9300 |
O1W—H2W | 0.8784 | C15—C16 | 1.421 (4) |
N1—C9 | 1.353 (4) | C16—C17 | 1.392 (4) |
N1—C1 | 1.411 (4) | C16—H16A | 0.9300 |
N1—C20 | 1.470 (4) | C17—H17A | 0.9300 |
N2—C15 | 1.368 (4) | C18—H18A | 0.9600 |
N2—C18 | 1.446 (4) | C18—H18B | 0.9600 |
N2—C19 | 1.453 (4) | C18—H18C | 0.9600 |
C1—C2 | 1.395 (4) | C19—H19A | 0.9600 |
C1—C6 | 1.409 (4) | C19—H19B | 0.9600 |
C2—C3 | 1.358 (4) | C19—H19C | 0.9600 |
C2—H2A | 0.9300 | C20—H20A | 0.9600 |
C3—C4 | 1.374 (4) | C20—H20B | 0.9600 |
C3—H3A | 0.9300 | C20—H20C | 0.9600 |
C4—C5 | 1.375 (5) | C21—C22 | 1.382 (4) |
C4—H4A | 0.9300 | C21—C26 | 1.385 (4) |
C5—C6 | 1.423 (4) | C22—C23 | 1.376 (4) |
C5—H5A | 0.9300 | C22—H22A | 0.9300 |
C6—C7 | 1.416 (4) | C23—C24 | 1.393 (4) |
C7—C8 | 1.336 (4) | C23—H23A | 0.9300 |
C7—H7A | 0.9300 | C24—C25 | 1.382 (4) |
C8—C9 | 1.451 (4) | C24—C27 | 1.509 (4) |
C8—H8A | 0.9300 | C25—C26 | 1.385 (4) |
C9—C10 | 1.423 (4) | C25—H25A | 0.9300 |
C10—C11 | 1.328 (4) | C26—H26A | 0.9300 |
C10—H10A | 0.9300 | C27—H27A | 0.9600 |
C11—C12 | 1.455 (4) | C27—H27B | 0.9600 |
C11—H11A | 0.9300 | C27—H27C | 0.9600 |
C12—C13 | 1.392 (4) | ||
O3—S1—O2 | 113.8 (2) | C13—C14—H14A | 119.1 |
O3—S1—O1 | 113.16 (16) | C15—C14—H14A | 119.1 |
O2—S1—O1 | 112.01 (18) | N2—C15—C14 | 121.4 (3) |
O3—S1—C21 | 105.11 (14) | N2—C15—C16 | 121.8 (3) |
O2—S1—C21 | 105.52 (15) | C14—C15—C16 | 116.8 (3) |
O1—S1—C21 | 106.33 (13) | C17—C16—C15 | 120.1 (3) |
H1W—O1W—H2W | 102.3 | C17—C16—H16A | 119.9 |
C9—N1—C1 | 123.0 (3) | C15—C16—H16A | 119.9 |
C9—N1—C20 | 119.4 (3) | C16—C17—C12 | 121.9 (3) |
C1—N1—C20 | 117.6 (2) | C16—C17—H17A | 119.0 |
C15—N2—C18 | 120.6 (3) | C12—C17—H17A | 119.0 |
C15—N2—C19 | 120.8 (3) | N2—C18—H18A | 109.5 |
C18—N2—C19 | 117.9 (3) | N2—C18—H18B | 109.5 |
C2—C1—C6 | 119.8 (3) | H18A—C18—H18B | 109.5 |
C2—C1—N1 | 121.8 (3) | N2—C18—H18C | 109.5 |
C6—C1—N1 | 118.4 (3) | H18A—C18—H18C | 109.5 |
C3—C2—C1 | 119.4 (3) | H18B—C18—H18C | 109.5 |
C3—C2—H2A | 120.3 | N2—C19—H19A | 109.5 |
C1—C2—H2A | 120.3 | N2—C19—H19B | 109.5 |
C2—C3—C4 | 122.7 (3) | H19A—C19—H19B | 109.5 |
C2—C3—H3A | 118.7 | N2—C19—H19C | 109.5 |
C4—C3—H3A | 118.7 | H19A—C19—H19C | 109.5 |
C3—C4—C5 | 119.6 (3) | H19B—C19—H19C | 109.5 |
C3—C4—H4A | 120.2 | N1—C20—H20A | 109.5 |
C5—C4—H4A | 120.2 | N1—C20—H20B | 109.5 |
C4—C5—C6 | 119.7 (3) | H20A—C20—H20B | 109.5 |
C4—C5—H5A | 120.1 | N1—C20—H20C | 109.5 |
C6—C5—H5A | 120.1 | H20A—C20—H20C | 109.5 |
C1—C6—C7 | 119.2 (3) | H20B—C20—H20C | 109.5 |
C1—C6—C5 | 118.8 (3) | C22—C21—C26 | 119.7 (3) |
C7—C6—C5 | 122.0 (3) | C22—C21—S1 | 119.5 (2) |
C8—C7—C6 | 120.4 (3) | C26—C21—S1 | 120.8 (2) |
C8—C7—H7A | 119.8 | C23—C22—C21 | 120.1 (3) |
C6—C7—H7A | 119.8 | C23—C22—H22A | 120.0 |
C7—C8—C9 | 121.9 (3) | C21—C22—H22A | 120.0 |
C7—C8—H8A | 119.0 | C22—C23—C24 | 121.2 (3) |
C9—C8—H8A | 119.0 | C22—C23—H23A | 119.4 |
N1—C9—C10 | 122.7 (3) | C24—C23—H23A | 119.4 |
N1—C9—C8 | 116.9 (3) | C25—C24—C23 | 117.8 (3) |
C10—C9—C8 | 120.4 (3) | C25—C24—C27 | 121.3 (3) |
C11—C10—C9 | 126.0 (3) | C23—C24—C27 | 120.9 (3) |
C11—C10—H10A | 117.0 | C24—C25—C26 | 121.6 (3) |
C9—C10—H10A | 117.0 | C24—C25—H25A | 119.2 |
C10—C11—C12 | 127.1 (3) | C26—C25—H25A | 119.2 |
C10—C11—H11A | 116.4 | C21—C26—C25 | 119.5 (3) |
C12—C11—H11A | 116.4 | C21—C26—H26A | 120.3 |
C13—C12—C17 | 117.2 (3) | C25—C26—H26A | 120.3 |
C13—C12—C11 | 119.0 (3) | C24—C27—H27A | 109.5 |
C17—C12—C11 | 123.8 (3) | C24—C27—H27B | 109.5 |
C14—C13—C12 | 122.2 (3) | H27A—C27—H27B | 109.5 |
C14—C13—H13A | 118.9 | C24—C27—H27C | 109.5 |
C12—C13—H13A | 118.9 | H27A—C27—H27C | 109.5 |
C13—C14—C15 | 121.9 (3) | H27B—C27—H27C | 109.5 |
C9—N1—C1—C2 | −178.0 (3) | C11—C12—C13—C14 | −178.1 (3) |
C20—N1—C1—C2 | 1.2 (4) | C12—C13—C14—C15 | −0.2 (5) |
C9—N1—C1—C6 | 0.9 (4) | C18—N2—C15—C14 | 3.6 (4) |
C20—N1—C1—C6 | −179.9 (3) | C19—N2—C15—C14 | 174.2 (3) |
C6—C1—C2—C3 | 0.3 (4) | C18—N2—C15—C16 | −176.9 (3) |
N1—C1—C2—C3 | 179.2 (3) | C19—N2—C15—C16 | −6.3 (4) |
C1—C2—C3—C4 | −0.6 (5) | C13—C14—C15—N2 | 179.6 (3) |
C2—C3—C4—C5 | 0.5 (5) | C13—C14—C15—C16 | 0.1 (4) |
C3—C4—C5—C6 | −0.2 (5) | N2—C15—C16—C17 | −179.1 (3) |
C2—C1—C6—C7 | −179.6 (3) | C14—C15—C16—C17 | 0.4 (4) |
N1—C1—C6—C7 | 1.5 (4) | C15—C16—C17—C12 | −0.9 (4) |
C2—C1—C6—C5 | 0.0 (4) | C13—C12—C17—C16 | 0.7 (4) |
N1—C1—C6—C5 | −178.9 (3) | C11—C12—C17—C16 | 178.6 (3) |
C4—C5—C6—C1 | −0.1 (4) | O3—S1—C21—C22 | 53.9 (3) |
C4—C5—C6—C7 | 179.5 (3) | O2—S1—C21—C22 | 174.5 (3) |
C1—C6—C7—C8 | −1.3 (4) | O1—S1—C21—C22 | −66.3 (3) |
C5—C6—C7—C8 | 179.2 (3) | O3—S1—C21—C26 | −125.2 (3) |
C6—C7—C8—C9 | −1.3 (5) | O2—S1—C21—C26 | −4.6 (3) |
C1—N1—C9—C10 | 176.0 (3) | O1—S1—C21—C26 | 114.6 (2) |
C20—N1—C9—C10 | −3.3 (4) | C26—C21—C22—C23 | 1.4 (5) |
C1—N1—C9—C8 | −3.3 (4) | S1—C21—C22—C23 | −177.7 (2) |
C20—N1—C9—C8 | 177.5 (3) | C21—C22—C23—C24 | 0.2 (5) |
C7—C8—C9—N1 | 3.5 (4) | C22—C23—C24—C25 | −1.1 (5) |
C7—C8—C9—C10 | −175.8 (3) | C22—C23—C24—C27 | 177.6 (3) |
N1—C9—C10—C11 | −179.3 (3) | C23—C24—C25—C26 | 0.6 (4) |
C8—C9—C10—C11 | −0.1 (5) | C27—C24—C25—C26 | −178.1 (3) |
C9—C10—C11—C12 | 179.5 (3) | C22—C21—C26—C25 | −1.9 (4) |
C10—C11—C12—C13 | −179.7 (3) | S1—C21—C26—C25 | 177.2 (2) |
C10—C11—C12—C17 | 2.4 (5) | C24—C25—C26—C21 | 0.9 (4) |
C17—C12—C13—C14 | −0.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O2 | 0.90 | 1.96 | 2.839 (4) | 164 |
O1W—H2W···O1i | 0.88 | 2.01 | 2.893 (3) | 179 |
C10—H10A···O3ii | 0.93 | 2.57 | 3.460 (4) | 162 |
C17—H17A···O3ii | 0.93 | 2.45 | 3.344 (5) | 163 |
C20—H20A···O3ii | 0.96 | 2.33 | 3.204 (6) | 151 |
C20—H20B···O1iii | 0.96 | 2.49 | 3.388 (4) | 156 |
C26—H26A···O2 | 0.93 | 2.51 | 2.884 (5) | 104 |
C7—H7A···Cg4iv | 0.93 | 2.97 | 3.615 (4) | 128 |
C23—H23A···Cg3v | 0.93 | 2.82 | 3.594 (4) | 141 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C20H21N2+·C7H7O3S−·H2O |
Mr | 478.60 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 10.9739 (5), 11.1789 (5), 11.1923 (9) |
α, β, γ (°) | 97.133 (5), 100.322 (5), 117.021 (3) |
V (Å3) | 1169.78 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.24 × 0.19 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEX2 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.958, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17557, 5390, 3272 |
Rint | 0.073 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.072, 0.203, 1.05 |
No. of reflections | 5390 |
No. of parameters | 311 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.60, −0.47 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O2 | 0.90 | 1.96 | 2.839 (4) | 164 |
O1W—H2W···O1i | 0.88 | 2.01 | 2.893 (3) | 179 |
C10—H10A···O3ii | 0.93 | 2.57 | 3.460 (4) | 162 |
C17—H17A···O3ii | 0.93 | 2.45 | 3.344 (5) | 163 |
C20—H20A···O3ii | 0.96 | 2.33 | 3.204 (6) | 151 |
C20—H20B···O1iii | 0.96 | 2.49 | 3.388 (4) | 156 |
C26—H26A···O2 | 0.93 | 2.51 | 2.884 (5) | 104 |
C7—H7A···Cg4iv | 0.93 | 2.97 | 3.615 (4) | 128 |
C23—H23A···Cg3v | 0.93 | 2.82 | 3.594 (4) | 141 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x+1, −y, −z. |
Acknowledgements
The authors thank the Prince of Songkla University for a research grant and also Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.
References
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There has been considerable interest in organic nonlinear optical materials that could be used for applications including telecommunications, optical computing and optical data storage. Organic crystals with extensive conjugated π systems are attractive candidates for nonlinear optic (NLO) studies because of their large hyperpolariability (β) and ease of preparation (Dittrich et al., 2003; Nogi et al., 2000; Ogawa et al., 2008; Otero et al., 2002; Sato et al., 1999; Weir et al., 2003; Yang et al., 2007). 4-N,N-dimethylamino-4'-N'-methyl-stilbazolium tosylate (DAST) is one of the promising NLO material (Adachi et al., 1999). Previous studies (Dittrich et al., 2003; Nogi et al., 2000; Sato et al., 1999) have shown that the DAST and its analogues exhibit second-order non-linear optical properties. One strategy to enhance the hyperpolariability of the cations is by elongation of its π-conjugation system. Based on these previous studies, we have synthesized the title compound which was designed by increasing the π-conjugate system with the replacement of the cationic pyridinium ring that is present in DAST by the quinolinium ring. The crystal structure of the title compound is reported in this study.
Figure 1 shows the asymmetric unit of the title compound (I) which consists of a C20H21N2+ cation, a C7H7O3S- anion and one H2O molecule. The cation exists in the E configuration with respect to the C10═C11 double bond [1.328 (4) Å, the corresponding value is 1.357 (2) Å in Chantrapromma et al., 2008]. The cation molecule is essentially planar as indicated by the dihedral angle between the quinolinium and the dimethylaminophenyl rings being 2.79 (13)° [9.26 (6) ° in Chantrapromma et al., 2008] with the torsion angles C8–C9–C10–C11 = -0.1 (5)° and C10–C11–C12–C17 = 2.4 (5)°. Both methyl groups of dimethylamino moiety are slightly twisted from the mean plane of the attached C12–C17 ring as indicated by the torsion angle C18—N2–C15–C14 = 3.6 (4)° and C19–N2–C15–C16 = -6.3 (4)°. The relative arrangement of cation and anion is shown by the interplanar angles between the mean plane of the 4-methylphenyl ring and those of the quinolinium and dimethylaminophenyl system which are 67.80 (13) and 67.19 (16)°, respectively. Besides the O—H···O hydrogen bonded to water molecule, the atom O2 of the sulfonate also contributed to a weak intramolecular C26—H26A···O2 interaction (Table 1) forming an S(5) ring motif (Bernstein et al., 1995). The bond lengths (Allen et al., 1987) and angles in (I) are in normal ranges and comparable with a related structure (Chantrapromma et al., 2008).
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 the anion by weak C—H···O interactions and the anion is further linked to the water molecule by O—H···O hydrogen bonds, forming a three-molecule unit (Table 1 and Fig. 2). These three-molecule units are arranged in a face-to-face manner into a ribbon-like structure along the b axis and these ribbons are stacked along the c axis (Fig. 2). The crystal structure is further stabilized by C—H···π interactions (Table 1). A π–π interaction with the distance Cg1···Cg2iv = 3.6074 (19) Å [symmetry code: (iv) 1 - x, -y, 1 - z] is observed; Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/C1/C6–C9, C1–C6, C12–C17 and C21–C26 rings, respectively.