2H-[1,3]Thia­zolo[5,4,3-ij]quinolin-3-ium chloride monohydrate

Ehweiner, M.A.; Belaj, F.; Mösch-Zanetti, N.C.

doi:10.1107/S2414314620014650

2H-[1,3]Thiazolo[5,4,3-ij]quinolin-3-ium chloride monohydrate

M. A. Ehweiner, F. Belaj and N. C. Mösch-Zanetti

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314620014650/hb4368sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314620014650/hb4368Isup2.hkl Contains datablock I
	MDL mol file https://doi.org/10.1107/S2414314620014650/hb4368Isup3.mol Supplementary material

CCDC reference: 2042568

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean () = 0.000 Å
Disorder in main residue
R factor = 0.042
wR factor = 0.096
Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.7 Note

Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            deep
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         27 Note
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report

Author Response: 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 of this disordered cation were restrained to have the same lengths (SAME of SHELXL).

PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report

Author Response: The positions of the H atoms of the water molecule were taken from a difference Fourier map, the O-H distances were fixed to 0.84A (DFIX of SHELXL), and the H atoms were refined with a common isotropic displacement parameter without any constraints to the bond angles.

PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report

Author Response: see response to the alert concerning the EADP record given above.

PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  1  )      17.06 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       2.94 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  Cl1      ..C24              3.13 Ang.
                                                      x,y,z  =      1_555 Check
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         16 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: 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).

2H-[1,3]Thiazolo[5,4,3-ij]quinolin-3-ium chloride monohydrate top

Crystal data top

C₁₀H₈NS⁺·Cl⁻·H₂O	F(000) = 472
M_r = 227.70	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	1968 independent reflections
Radiation source: Incoatec microfocus sealed tube	1474 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.056
φ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
T_min = 0.695, T_max = 1.000	k = −7→9
6361 measured reflections	l = −12→22

Refinement top

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(F_o²) + (0.026P)² + 0.8115P] where P = (F_o² + 2F_c²)/3
1968 reflections	(Δ/σ)_max = 0.001
179 parameters	Δρ_max = 0.32 e Å⁻³
16 restraints	Δρ_min = −0.30 e Å⁻³

Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

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2H-[1,3]Thia­zolo[5,4,3-ij]quinolin-3-ium chloride monohydrate

Supporting information

Key indicators

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2H-[1,3]Thiazolo[5,4,3-ij]quinolin-3-ium chloride monohydrate