organic compounds
2H-[1,3]Thiazolo[5,4,3-ij]quinolin-3-ium chloride monohydrate
aUniversity of Graz, Institute of Chemistry, Schubertstr. 1, 8010 Graz, Austria
*Correspondence e-mail: ferdinand.belaj@uni-graz.at
The structure of the title hydrated molecular salt, C10H8NS+·Cl−·H2O, obtained by the reaction of sodium quinoline-8-thiolate Na(Quin-8-S) with CH2Cl2 and an aqueous solution of [Bu4N]Cl, contains π-stacked cations [plane-to-plane separation = 3.338 (4)–3.356 (4) Å] and features chains built by alternating Cl− anions and H2O molecules connected by O—H⋯O hydrogen bonds. The cation shows whole-molecule disorder over two flipped orientations in a 0.853 (3):0.147 (3) ratio.
Keywords: crystal structure; quinoline; hydrogen bonding.
CCDC reference: 2042568
Structure description
The et al., 1993). All atoms lie on general positions but the cation is planar within experimental accuracy. It is disordered over two orientations with occupation factors of 0.853 (3) and 0.147 (3) that both occupy approximately the same space (Fig. 1). The cations show π-stacking in the a-axis direction (Fig. 2), with the cations and inversion centers alternating. The distances between their least-squares planes are alternately 3.338 (4) and 3.356 (4) Å. The chloride anions, together with the water molecules, form O—H⋯Cl hydrogen bonded (Table 1) zigzag chains running parallel to the b axis (Fig. 2).
analysis of the title compound is the first of this tricyclic cation. The anhydrous iodide compound has previously been synthesized (KimSynthesis and crystallization
During an attempt to obtain [Bu4N][Quin-8-S], an aqueous solution of [Bu4N]Cl was added to an aqueous solution of Na(Quin-8-S). The solution was then extracted with CH2Cl2 giving a yellow organic phase, which was then evaporated yielding a yellow oil. After a few hours, yellow–orange crystals of 2H-[1,3]thiazolo[5,4,3-ij]quinolin-3-ium chloride monohydrate had formed in the oil.
Refinement
Crystal data, data collection and structure . The thiazolo-quinolinium cation is disordered over two orientations, which refined to site occupation factors of 0.853 (3) and 0.147 (3), respectively. The same anisotropic displacement parameters were used for the ring atoms of the less occupied orientation and the equivalent bonds were restrained to have the same lengths.
details are summarized in Table 2Structural data
CCDC reference: 2042568
https://doi.org/10.1107/S2414314620014650/hb4368sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620014650/hb4368Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620014650/hb4368Isup3.mol
Data collection: APEX2 (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2015); molecular graphics: modified ORTEP (Johnson, 1965); software used to prepare material for publication: SHELXL2014/6 (Sheldrick, 2015).C10H8NS+·Cl−·H2O | F(000) = 472 |
Mr = 227.70 | Dx = 1.509 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.0543 (11) Å | Cell parameters from 1699 reflections |
b = 7.8252 (11) Å | θ = 2.8–26.1° |
c = 18.223 (3) Å | µ = 0.55 mm−1 |
β = 94.752 (7)° | T = 100 K |
V = 1002.5 (3) Å3 | Plate, deep yellow |
Z = 4 | 0.32 × 0.15 × 0.06 mm |
Bruker APEXII CCD diffractometer | 1968 independent reflections |
Radiation source: Incoatec microfocus sealed tube | 1474 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.056 |
φ and ω scans | θmax = 26.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −8→8 |
Tmin = 0.695, Tmax = 1.000 | k = −7→9 |
6361 measured reflections | l = −12→22 |
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)] = 0.042 | Hydrogen site location: mixed |
wR(F2) = 0.096 | Only H-atom displacement parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.026P)2 + 0.8115P] where P = (Fo2 + 2Fc2)/3 |
1968 reflections | (Δ/σ)max = 0.001 |
179 parameters | Δρmax = 0.32 e Å−3 |
16 restraints | Δρmin = −0.30 e Å−3 |
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 > 2σ(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. The thiazolo-quinolinium cation was disordered over two orientations which refined to site occupation factors of 0.853 (3) and 0.147 (3), respectively. The same anisotropic displacement parameters were used for the ring atoms of the less occupied orientation (EADP of SHELXL) and the equivalent bonds were restrained to have the same lengths (SAME of SHELXL). The positions of the H atoms of the water molecule were taken from a difference Fourier map, the O-H distances were fixed to 0.84 Å, and the H atoms were refined with a common isotropic displacement parameter without any constraints to the bond angles. The H atoms of the CH2 groups were refined with a common isotropic displacement parameter and idealized geometries with approximately tetrahedral angles and C-H distances of 0.99 Å (AFIX 23 of SHELXL). The H atoms of the quinoline rings were put at the external bisectors of the C-C-C angles at C-H distances of 0.95 Å and a common isotropic displacement parameter was refined for these H atoms (AFIX 43 of SHELXL). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.39598 (12) | 0.13216 (12) | 0.57556 (4) | 0.0214 (3) | 0.853 (3) |
C2 | 0.3490 (11) | 0.2798 (6) | 0.6496 (2) | 0.0205 (10) | 0.853 (3) |
H21 | 0.2482 | 0.2338 | 0.6788 | 0.029 (6)* | 0.853 (3) |
H22 | 0.4655 | 0.2976 | 0.6829 | 0.029 (6)* | 0.853 (3) |
N3 | 0.2867 (3) | 0.4431 (4) | 0.61387 (13) | 0.0153 (6) | 0.853 (3) |
C4 | 0.2379 (4) | 0.5808 (4) | 0.65067 (19) | 0.0233 (8) | 0.853 (3) |
H4 | 0.2434 | 0.5796 | 0.7029 | 0.027 (4)* | 0.853 (3) |
C5 | 0.1786 (10) | 0.7272 (6) | 0.61150 (19) | 0.0234 (14) | 0.853 (3) |
H5 | 0.1436 | 0.8264 | 0.6372 | 0.027 (4)* | 0.853 (3) |
C6 | 0.1707 (6) | 0.7285 (6) | 0.5367 (2) | 0.0246 (10) | 0.853 (3) |
H6 | 0.1309 | 0.8297 | 0.5111 | 0.027 (4)* | 0.853 (3) |
C7 | 0.2144 (18) | 0.5684 (10) | 0.4181 (3) | 0.0204 (11) | 0.853 (3) |
H7 | 0.1756 | 0.6616 | 0.3870 | 0.027 (4)* | 0.853 (3) |
C8 | 0.2661 (13) | 0.4161 (7) | 0.3889 (3) | 0.0208 (13) | 0.853 (3) |
H8 | 0.2660 | 0.4072 | 0.3369 | 0.027 (4)* | 0.853 (3) |
C9 | 0.3202 (9) | 0.2702 (7) | 0.43232 (19) | 0.0200 (10) | 0.853 (3) |
H9 | 0.3497 | 0.1651 | 0.4098 | 0.027 (4)* | 0.853 (3) |
C10 | 0.3286 (7) | 0.2850 (4) | 0.50763 (17) | 0.0149 (9) | 0.853 (3) |
C11 | 0.2783 (8) | 0.4407 (5) | 0.53779 (18) | 0.0134 (10) | 0.853 (3) |
C12 | 0.2196 (16) | 0.5844 (5) | 0.4958 (3) | 0.0183 (9) | 0.853 (3) |
Cl1 | 0.56970 (10) | 0.56684 (9) | 0.80204 (4) | 0.0255 (2) | |
O1 | 0.9855 (2) | 0.4364 (2) | 0.77707 (10) | 0.0274 (5) | |
H11 | 0.8735 (5) | 0.4705 (12) | 0.7800 (10) | 0.037 (7)* | |
H12 | 0.969 (3) | 0.3406 (4) | 0.7567 (4) | 0.037 (7)* | |
S2 | 0.1620 (9) | 0.8059 (9) | 0.5181 (4) | 0.0328 (18) | 0.147 (3) |
C22 | 0.206 (9) | 0.734 (3) | 0.6134 (7) | 0.0328 (18) | 0.147 (3) |
H221 | 0.3133 | 0.7991 | 0.6386 | 0.029 (6)* | 0.147 (3) |
H222 | 0.0920 | 0.7518 | 0.6404 | 0.029 (6)* | 0.147 (3) |
N23 | 0.254 (3) | 0.550 (3) | 0.6109 (10) | 0.0328 (18) | 0.147 (3) |
C24 | 0.302 (3) | 0.445 (2) | 0.6669 (12) | 0.0328 (18) | 0.147 (3) |
H24 | 0.2906 | 0.4853 | 0.7155 | 0.027 (4)* | 0.147 (3) |
C25 | 0.369 (8) | 0.280 (4) | 0.6575 (16) | 0.0328 (18) | 0.147 (3) |
H25 | 0.4197 | 0.2139 | 0.6985 | 0.027 (4)* | 0.147 (3) |
C26 | 0.360 (3) | 0.215 (3) | 0.5881 (12) | 0.0328 (18) | 0.147 (3) |
H26 | 0.3776 | 0.0953 | 0.5821 | 0.027 (4)* | 0.147 (3) |
C27 | 0.336 (7) | 0.275 (6) | 0.4491 (17) | 0.0328 (18) | 0.147 (3) |
H27 | 0.3914 | 0.1696 | 0.4368 | 0.027 (4)* | 0.147 (3) |
C28 | 0.269 (9) | 0.382 (6) | 0.394 (3) | 0.0328 (18) | 0.147 (3) |
H28 | 0.2510 | 0.3449 | 0.3440 | 0.027 (4)* | 0.147 (3) |
C29 | 0.228 (13) | 0.553 (7) | 0.414 (2) | 0.0328 (18) | 0.147 (3) |
H29 | 0.2043 | 0.6360 | 0.3769 | 0.027 (4)* | 0.147 (3) |
C30 | 0.220 (12) | 0.602 (3) | 0.487 (2) | 0.0328 (18) | 0.147 (3) |
C31 | 0.259 (7) | 0.480 (5) | 0.5414 (13) | 0.0328 (18) | 0.147 (3) |
C32 | 0.327 (6) | 0.317 (4) | 0.5245 (14) | 0.0328 (18) | 0.147 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0242 (5) | 0.0167 (5) | 0.0228 (4) | 0.0006 (4) | −0.0008 (3) | 0.0036 (3) |
C2 | 0.023 (3) | 0.0264 (19) | 0.0107 (16) | −0.0043 (16) | −0.0047 (16) | 0.0083 (14) |
N3 | 0.0105 (13) | 0.0221 (15) | 0.0134 (13) | −0.0035 (11) | 0.0019 (10) | −0.0009 (11) |
C4 | 0.0187 (18) | 0.033 (2) | 0.0190 (16) | −0.0096 (15) | 0.0062 (14) | −0.0105 (15) |
C5 | 0.014 (4) | 0.0217 (19) | 0.0346 (19) | −0.0044 (15) | 0.0052 (15) | −0.0142 (15) |
C6 | 0.0154 (19) | 0.020 (3) | 0.038 (2) | −0.0044 (18) | −0.0019 (16) | 0.0085 (19) |
C7 | 0.011 (3) | 0.027 (3) | 0.0225 (18) | −0.003 (2) | −0.0034 (15) | 0.0107 (16) |
C8 | 0.0154 (17) | 0.037 (4) | 0.0101 (15) | −0.005 (3) | 0.0005 (13) | 0.0014 (17) |
C9 | 0.014 (2) | 0.027 (2) | 0.0187 (19) | −0.0008 (16) | −0.0056 (19) | −0.009 (2) |
C10 | 0.0109 (15) | 0.0163 (19) | 0.0169 (19) | −0.0035 (16) | −0.0020 (17) | 0.0015 (14) |
C11 | 0.005 (2) | 0.024 (3) | 0.0111 (14) | −0.004 (2) | 0.0006 (12) | 0.0009 (13) |
C12 | 0.0078 (15) | 0.020 (2) | 0.027 (2) | −0.005 (2) | −0.001 (2) | −0.0029 (17) |
Cl1 | 0.0225 (4) | 0.0236 (4) | 0.0308 (4) | −0.0005 (3) | 0.0038 (3) | −0.0017 (3) |
O1 | 0.0209 (11) | 0.0319 (12) | 0.0291 (11) | 0.0027 (9) | 0.0003 (9) | 0.0007 (9) |
S2 | 0.015 (3) | 0.028 (4) | 0.054 (4) | 0.001 (2) | −0.009 (2) | −0.006 (3) |
C22 | 0.015 (3) | 0.028 (4) | 0.054 (4) | 0.001 (2) | −0.009 (2) | −0.006 (3) |
N23 | 0.015 (3) | 0.028 (4) | 0.054 (4) | 0.001 (2) | −0.009 (2) | −0.006 (3) |
C24 | 0.015 (3) | 0.028 (4) | 0.054 (4) | 0.001 (2) | −0.009 (2) | −0.006 (3) |
C25 | 0.015 (3) | 0.028 (4) | 0.054 (4) | 0.001 (2) | −0.009 (2) | −0.006 (3) |
C26 | 0.015 (3) | 0.028 (4) | 0.054 (4) | 0.001 (2) | −0.009 (2) | −0.006 (3) |
C27 | 0.015 (3) | 0.028 (4) | 0.054 (4) | 0.001 (2) | −0.009 (2) | −0.006 (3) |
C28 | 0.015 (3) | 0.028 (4) | 0.054 (4) | 0.001 (2) | −0.009 (2) | −0.006 (3) |
C29 | 0.015 (3) | 0.028 (4) | 0.054 (4) | 0.001 (2) | −0.009 (2) | −0.006 (3) |
C30 | 0.015 (3) | 0.028 (4) | 0.054 (4) | 0.001 (2) | −0.009 (2) | −0.006 (3) |
C31 | 0.015 (3) | 0.028 (4) | 0.054 (4) | 0.001 (2) | −0.009 (2) | −0.006 (3) |
C32 | 0.015 (3) | 0.028 (4) | 0.054 (4) | 0.001 (2) | −0.009 (2) | −0.006 (3) |
S1—C2 | 1.827 (4) | O1—H12 | 0.84 |
S1—C10 | 1.758 (4) | S2—C30 | 1.758 (6) |
N3—C2 | 1.484 (5) | S2—C22 | 1.827 (6) |
C2—H21 | 0.99 | C22—N23 | 1.484 (6) |
C2—H22 | 0.99 | C22—H221 | 0.99 |
N3—C4 | 1.329 (4) | C22—H222 | 0.99 |
N3—C11 | 1.383 (4) | N23—C24 | 1.329 (5) |
C4—C5 | 1.395 (5) | N23—C31 | 1.384 (5) |
C4—H4 | 0.95 | C24—C25 | 1.395 (7) |
C5—C6 | 1.360 (5) | C24—H24 | 0.95 |
C5—H5 | 0.95 | C25—C26 | 1.360 (7) |
C6—C12 | 1.409 (5) | C25—H25 | 0.95 |
C6—H6 | 0.95 | C26—C32 | 1.411 (7) |
C7—C8 | 1.366 (5) | C26—H26 | 0.95 |
C7—C12 | 1.420 (5) | C27—C28 | 1.366 (6) |
C7—H7 | 0.95 | C27—C32 | 1.419 (6) |
C8—C9 | 1.423 (5) | C27—H27 | 0.95 |
C8—H8 | 0.95 | C28—C29 | 1.423 (7) |
C9—C10 | 1.374 (4) | C28—H28 | 0.95 |
C9—H9 | 0.95 | C29—C30 | 1.373 (6) |
C10—C11 | 1.394 (4) | C29—H29 | 0.95 |
C11—C12 | 1.403 (5) | C30—C31 | 1.394 (6) |
O1—H11 | 0.84 | C31—C32 | 1.402 (6) |
N3—C2—S1 | 106.6 (2) | C30—S2—C22 | 90.3 (14) |
N3—C2—H21 | 110.4 | N23—C22—S2 | 106.9 (11) |
S1—C2—H21 | 110.4 | N23—C22—H221 | 110.3 |
N3—C2—H22 | 110.4 | S2—C22—H221 | 110.3 |
S1—C2—H22 | 110.4 | N23—C22—H222 | 110.3 |
H21—C2—H22 | 108.6 | S2—C22—H222 | 110.3 |
C2—S1—C10 | 91.98 (16) | H221—C22—H222 | 108.6 |
S1—C10—C9 | 129.2 (3) | C24—N23—C31 | 116 (3) |
S1—C10—C11 | 112.3 (2) | C24—N23—C22 | 128.2 (18) |
C9—C10—C11 | 118.4 (4) | C31—N23—C22 | 116 (2) |
C10—C11—N3 | 114.6 (3) | N23—C24—C25 | 123 (3) |
C12—C11—N3 | 121.4 (3) | N23—C24—H24 | 118.5 |
C10—C11—C12 | 124.0 (3) | C25—C24—H24 | 118.5 |
C11—N3—C2 | 114.5 (3) | C26—C25—C24 | 118 (3) |
C11—N3—C4 | 121.7 (3) | C26—C25—H25 | 121.0 |
C2—N3—C4 | 123.8 (3) | C24—C25—H25 | 121.0 |
N3—C4—C5 | 119.1 (4) | C25—C26—C32 | 123 (3) |
N3—C4—H4 | 120.5 | C25—C26—H26 | 118.5 |
C5—C4—H4 | 120.5 | C32—C26—H26 | 118.5 |
C6—C5—C4 | 120.3 (4) | C28—C27—C32 | 122 (4) |
C6—C5—H5 | 119.8 | C28—C27—H27 | 118.8 |
C4—C5—H5 | 119.8 | C32—C27—H27 | 118.8 |
C5—C6—C12 | 122.1 (4) | C27—C28—C29 | 116 (5) |
C5—C6—H6 | 118.9 | C27—C28—H28 | 121.9 |
C12—C6—H6 | 118.9 | C29—C28—H28 | 121.9 |
C8—C7—C12 | 118.6 (6) | C30—C29—C28 | 123 (5) |
C8—C7—H7 | 120.7 | C30—C29—H29 | 118.6 |
C12—C7—H7 | 120.7 | C28—C29—H29 | 118.6 |
C7—C8—C9 | 123.5 (6) | C29—C30—C31 | 118 (3) |
C7—C8—H8 | 118.3 | C29—C30—S2 | 127 (3) |
C9—C8—H8 | 118.3 | C31—C30—S2 | 115 (2) |
C10—C9—C8 | 118.4 (5) | N23—C31—C30 | 112 (3) |
C10—C9—H9 | 120.8 | N23—C31—C32 | 127 (3) |
C8—C9—H9 | 120.8 | C30—C31—C32 | 121.1 (17) |
C11—C12—C6 | 115.3 (4) | C31—C32—C26 | 112 (3) |
C11—C12—C7 | 117.1 (4) | C31—C32—C27 | 118 (2) |
C6—C12—C7 | 127.6 (5) | C26—C32—C27 | 130 (3) |
H11—O1—H12 | 102.2 (17) | ||
C10—S1—C2—N3 | −1.3 (5) | C30—S2—C22—N23 | −3 (4) |
S1—C2—N3—C4 | 179.3 (3) | S2—C22—N23—C24 | 178 (2) |
S1—C2—N3—C11 | 0.8 (6) | S2—C22—N23—C31 | 2 (5) |
C11—N3—C4—C5 | −0.6 (6) | C31—N23—C24—C25 | 5 (5) |
C2—N3—C4—C5 | −179.0 (6) | C22—N23—C24—C25 | −171 (5) |
N3—C4—C5—C6 | 0.1 (8) | N23—C24—C25—C26 | −9 (6) |
C4—C5—C6—C12 | 0.5 (10) | C24—C25—C26—C32 | 14 (6) |
C12—C7—C8—C9 | 1.9 (17) | C32—C27—C28—C29 | 14 (9) |
C7—C8—C9—C10 | −2.8 (13) | C27—C28—C29—C30 | −12 (12) |
C8—C9—C10—C11 | 1.9 (9) | C28—C29—C30—C31 | 1 (13) |
C8—C9—C10—S1 | −178.0 (5) | C28—C29—C30—S2 | −177 (6) |
C2—S1—C10—C9 | −178.5 (6) | C22—S2—C30—C29 | −177 (8) |
C2—S1—C10—C11 | 1.6 (5) | C22—S2—C30—C31 | 4 (6) |
C4—N3—C11—C10 | −178.1 (4) | C24—N23—C31—C30 | −176 (5) |
C2—N3—C11—C10 | 0.4 (7) | C22—N23—C31—C30 | 1 (7) |
C4—N3—C11—C12 | 0.6 (9) | C24—N23—C31—C32 | −7 (7) |
C2—N3—C11—C12 | 179.2 (7) | C22—N23—C31—C32 | 170 (5) |
C9—C10—C11—N3 | 178.6 (5) | C29—C30—C31—N23 | 177 (7) |
S1—C10—C11—N3 | −1.5 (6) | S2—C30—C31—N23 | −4 (8) |
C9—C10—C11—C12 | −0.1 (11) | C29—C30—C31—C32 | 8 (11) |
S1—C10—C11—C12 | 179.8 (7) | S2—C30—C31—C32 | −173 (4) |
N3—C11—C12—C6 | 0.0 (12) | N23—C31—C32—C26 | 11 (7) |
C10—C11—C12—C6 | 178.6 (6) | C30—C31—C32—C26 | 179 (5) |
N3—C11—C12—C7 | −179.5 (8) | N23—C31—C32—C27 | −174 (4) |
C10—C11—C12—C7 | −0.8 (14) | C30—C31—C32—C27 | −6 (9) |
C5—C6—C12—C11 | −0.5 (12) | C25—C26—C32—C31 | −14 (6) |
C5—C6—C12—C7 | 178.8 (10) | C25—C26—C32—C27 | 171 (5) |
C8—C7—C12—C11 | 0.0 (16) | C28—C27—C32—C31 | −5 (8) |
C8—C7—C12—C6 | −179.4 (10) | C28—C27—C32—C26 | 169 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H11···Cl1 | 0.84 | 2.34 (1) | 3.174 (2) | 174 (2) |
O1—H12···Cl1i | 0.84 | 2.40 (1) | 3.240 (2) | 178 (2) |
Symmetry code: (i) −x+3/2, y−1/2, −z+3/2. |
Funding information
Financial support by NAWI Graz is gratefully acknowledged.
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