1-(Hex-5-en-1-yl)-4-{[3-methyl-2,3-di­hydro-1,3-benzo­thia­zol-2-yl­idene]meth­yl}quinolin-1-ium iodide monohydrate

The title thia­zole orange derivative, bearing an alkene substituent, crystallized as a monohydrate of its iodide salt, namely, (Z)-1-(hex-5-en-1-yl)-4-{[3-methyl-2,3-di­hydro-1,3-benzo­thia­zol-2-yl­idene]meth­yl}quinolin-1-ium iodide monohydrate, C₂₄H₂₅N₂S⁺·I⁻·H₂O. The packing features aromatic π-stacking and van der Waals inter­actions. The water mol­ecule of crystallization inter­acts with the cation and anion via O—H...N and O—H...I hydrogen bonds, respectively.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.060
• wR factor = 0.171
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C13 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C12 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including        O1      0.138 Check
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01182 Ang.
PLAT368_ALERT_2_C Short  C(sp2)-C(sp2) Bond  C14      - C15      .       1.20 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H5       ..H16      .       1.98 Ang.
                                                      x,y,z  =      1_555 Check
PLAT976_ALERT_2_C Check Calcd Resid. Dens.  0.73A   From O1             -0.51 eA-3
PLAT976_ALERT_2_C Check Calcd Resid. Dens.  0.70A   From O1             -0.50 eA-3
PLAT976_ALERT_2_C Check Calcd Resid. Dens.  0.72A   From O1             -0.40 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C24 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note

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

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

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1-(Hex-5-en-1-yl)-4-{[3-methyl-2,3-dihydro-1,3-benzothiazol-2-ylidene]methyl}quinolin-1-ium iodide monohydrate

Crystal data

C24H25N2S^+·I^−·H2O	Z = 2
Mr = 518.43	F(000) = 524
Triclinic, P1	Dx = 1.505 Mg m^−3
a = 8.4780 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5773 (17) Å	Cell parameters from 644 reflections
c = 14.5191 (19) Å	θ = 2.1–21.1°
α = 95.810 (12)°	µ = 1.51 mm^−1
β = 105.762 (12)°	T = 170 K
γ = 110.651 (14)°	Rect. prism, clear dark red
V = 1144.1 (3) Å^3	0.5 × 0.1 × 0.1 mm

Data collection

XtaLAB Mini (ROW) diffractometer	4189 independent reflections
Radiation source: fine-focus sealed X-ray tube, Rigaku (Mo) X-ray Source	2249 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scans	θmax = 25.4°, θmin = 2.1°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	h = −10→10
Tmin = 0.332, Tmax = 1.000	k = −12→11
6581 measured reflections	l = −17→16

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.171	w = 1/[σ^2(Fo^2) + (0.0622P)^2 + 0.1317P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4189 reflections	Δρmax = 0.66 e Å^−3
266 parameters	Δρmin = −0.60 e Å^−3
0 restraints

Special details

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. All H atoms were placed in idealized locations (C—H = 0.93–0.97, O—H = 0.85 Å) and refined as riding atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.04034 (9)	0.55965 (6)	0.30846 (5)	0.0920 (3)
S1	0.7927 (3)	0.81364 (17)	0.36094 (14)	0.0577 (5)
N2	0.8314 (7)	1.0670 (5)	0.3757 (4)	0.0495 (14)
N1	0.6019 (8)	0.6852 (5)	0.6841 (5)	0.0579 (15)
C23	0.8637 (9)	1.0327 (7)	0.2901 (5)	0.0511 (17)
C4	0.6594 (9)	0.9170 (7)	0.6522 (5)	0.0498 (17)
C16	0.7461 (9)	0.9748 (7)	0.5082 (5)	0.0537 (17)
H16	0.746994	1.060734	0.530348	0.064*
C3	0.7026 (9)	0.8785 (6)	0.5662 (5)	0.0486 (17)
C17	0.7876 (8)	0.9617 (6)	0.4235 (5)	0.0467 (16)
C9	0.6078 (9)	0.8171 (7)	0.7091 (5)	0.0549 (18)
C2	0.6923 (9)	0.7436 (7)	0.5470 (5)	0.0559 (18)
H2	0.716781	0.713601	0.492143	0.067*
C1	0.6479 (9)	0.6548 (7)	0.6053 (5)	0.0590 (19)
H1	0.649126	0.567645	0.590268	0.071*
C18	0.8509 (9)	0.8971 (7)	0.2716 (5)	0.0544 (18)
C22	0.9072 (10)	1.1178 (8)	0.2252 (6)	0.066 (2)
H22	0.918042	1.209023	0.236988	0.080*
C10	0.5465 (10)	0.5769 (7)	0.7392 (6)	0.067 (2)
H10A	0.515625	0.487592	0.698316	0.080*
H10B	0.439612	0.576184	0.751890	0.080*
C5	0.6653 (10)	1.0472 (7)	0.6860 (5)	0.0609 (19)
H5	0.701850	1.115918	0.652057	0.073*
C11	0.6831 (11)	0.5937 (7)	0.8340 (6)	0.066 (2)
H11A	0.705991	0.678282	0.878000	0.079*
H11B	0.793698	0.601946	0.822871	0.079*
C6	0.6208 (11)	1.0797 (8)	0.7658 (6)	0.072 (2)
H6	0.624418	1.167804	0.783995	0.086*
C24	0.8400 (10)	1.2008 (7)	0.4111 (6)	0.064 (2)
H24A	0.927482	1.239531	0.475373	0.096*
H24B	0.725376	1.193066	0.414159	0.096*
H24C	0.872977	1.259910	0.367520	0.096*
C8	0.5616 (11)	0.8527 (8)	0.7912 (6)	0.071 (2)
H8	0.524265	0.786504	0.826843	0.085*
O1	0.2316 (12)	0.5102 (8)	0.5443 (7)	0.138 (3)
H1A	0.291275	0.581291	0.590880	0.207*
H1B	0.192515	0.534755	0.491739	0.207*
C19	0.8832 (11)	0.8450 (8)	0.1895 (6)	0.073 (2)
H19	0.877847	0.755232	0.177902	0.087*
C12	0.6232 (11)	0.4721 (8)	0.8818 (6)	0.071 (2)
H12A	0.512182	0.464089	0.892323	0.085*
H12B	0.599653	0.387829	0.837227	0.085*
C20	0.9230 (12)	0.9296 (9)	0.1268 (6)	0.081 (2)
H20	0.943321	0.895594	0.071436	0.097*
C21	0.9340 (11)	1.0618 (9)	0.1423 (6)	0.075 (2)
H21	0.959534	1.115594	0.097174	0.090*
C7	0.5706 (12)	0.9825 (9)	0.8191 (7)	0.080 (3)
H7	0.542670	1.005128	0.874551	0.095*
C13	0.7538 (14)	0.4843 (11)	0.9753 (8)	0.110 (3)
H13A	0.770531	0.565495	1.020756	0.132*
H13B	0.867061	0.500098	0.965176	0.132*
C14	0.7080 (18)	0.3633 (12)	1.0222 (8)	0.113 (4)
H14	0.790099	0.376037	1.083381	0.136*
C15	0.585 (2)	0.2529 (12)	0.9957 (10)	0.146 (6)
H15A	0.496588	0.231168	0.935308	0.175*
H15B	0.578332	0.188806	1.035348	0.175*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.1378 (6)	0.0665 (4)	0.0968 (5)	0.0488 (4)	0.0612 (4)	0.0317 (3)
S1	0.0704 (12)	0.0407 (9)	0.0605 (12)	0.0162 (9)	0.0271 (10)	0.0111 (9)
N2	0.057 (4)	0.041 (3)	0.055 (4)	0.019 (3)	0.024 (3)	0.018 (3)
N1	0.058 (4)	0.041 (3)	0.072 (4)	0.011 (3)	0.029 (3)	0.016 (3)
C23	0.045 (4)	0.048 (4)	0.056 (5)	0.010 (3)	0.019 (4)	0.014 (4)
C4	0.053 (4)	0.043 (4)	0.061 (5)	0.019 (3)	0.028 (4)	0.017 (3)
C16	0.060 (5)	0.046 (4)	0.061 (5)	0.021 (4)	0.028 (4)	0.017 (4)
C3	0.048 (4)	0.043 (4)	0.055 (4)	0.016 (3)	0.018 (3)	0.016 (3)
C17	0.038 (4)	0.042 (4)	0.058 (5)	0.010 (3)	0.018 (3)	0.014 (3)
C9	0.050 (4)	0.058 (4)	0.064 (5)	0.024 (4)	0.025 (4)	0.020 (4)
C2	0.069 (5)	0.048 (4)	0.057 (5)	0.019 (4)	0.033 (4)	0.018 (4)
C1	0.069 (5)	0.047 (4)	0.060 (5)	0.018 (4)	0.027 (4)	0.008 (4)
C18	0.057 (5)	0.047 (4)	0.055 (5)	0.013 (4)	0.023 (4)	0.013 (4)
C22	0.066 (5)	0.068 (5)	0.075 (6)	0.028 (4)	0.033 (4)	0.027 (5)
C10	0.084 (6)	0.050 (4)	0.070 (5)	0.016 (4)	0.042 (5)	0.024 (4)
C5	0.078 (5)	0.057 (4)	0.062 (5)	0.031 (4)	0.035 (4)	0.022 (4)
C11	0.080 (5)	0.059 (5)	0.073 (6)	0.030 (4)	0.039 (5)	0.024 (4)
C6	0.101 (6)	0.062 (5)	0.083 (6)	0.045 (5)	0.059 (5)	0.026 (4)
C24	0.073 (5)	0.054 (4)	0.077 (6)	0.027 (4)	0.036 (4)	0.027 (4)
C8	0.088 (6)	0.078 (5)	0.082 (6)	0.043 (5)	0.060 (5)	0.042 (5)
O1	0.121 (7)	0.111 (6)	0.159 (8)	0.044 (6)	0.020 (6)	0.009 (5)
C19	0.091 (6)	0.058 (5)	0.066 (5)	0.015 (5)	0.043 (5)	0.006 (4)
C12	0.081 (6)	0.063 (5)	0.078 (6)	0.028 (5)	0.039 (5)	0.025 (5)
C20	0.093 (7)	0.078 (6)	0.068 (6)	0.016 (5)	0.048 (5)	0.009 (5)
C21	0.084 (6)	0.072 (5)	0.070 (6)	0.017 (5)	0.040 (5)	0.028 (5)
C7	0.106 (7)	0.080 (6)	0.096 (7)	0.057 (6)	0.069 (6)	0.035 (5)
C13	0.123 (9)	0.109 (8)	0.108 (8)	0.051 (7)	0.039 (7)	0.052 (7)
C14	0.159 (11)	0.105 (8)	0.094 (8)	0.060 (9)	0.051 (8)	0.051 (7)
C15	0.259 (18)	0.093 (8)	0.128 (11)	0.065 (11)	0.129 (12)	0.048 (8)

Geometric parameters (Å, º)

S1—C17	1.750 (7)	C11—H11A	0.9700
S1—C18	1.726 (7)	C11—H11B	0.9700
N2—C23	1.383 (8)	C11—C12	1.518 (9)
N2—C17	1.366 (8)	C6—H6	0.9300
N2—C24	1.426 (8)	C6—C7	1.367 (10)
N1—C9	1.385 (8)	C24—H24A	0.9600
N1—C1	1.349 (9)	C24—H24B	0.9600
N1—C10	1.478 (8)	C24—H24C	0.9600
C23—C18	1.392 (9)	C8—H8	0.9300
C23—C22	1.400 (10)	C8—C7	1.361 (10)
C4—C3	1.453 (9)	O1—H1A	0.8500
C4—C9	1.427 (9)	O1—H1B	0.8499
C4—C5	1.393 (9)	C19—H19	0.9300
C16—H16	0.9300	C19—C20	1.365 (11)
C16—C3	1.399 (9)	C12—H12A	0.9700
C16—C17	1.375 (9)	C12—H12B	0.9700
C3—C2	1.392 (9)	C12—C13	1.461 (11)
C9—C8	1.408 (10)	C20—H20	0.9300
C2—H2	0.9300	C20—C21	1.360 (11)
C2—C1	1.351 (9)	C21—H21	0.9300
C1—H1	0.9300	C7—H7	0.9300
C18—C19	1.397 (10)	C13—H13A	0.9700
C22—H22	0.9300	C13—H13B	0.9700
C22—C21	1.396 (11)	C13—C14	1.491 (13)
C10—H10A	0.9700	C14—H14	0.9300
C10—H10B	0.9700	C14—C15	1.196 (15)
C10—C11	1.485 (10)	C15—H15A	0.9300
C5—H5	0.9300	C15—H15B	0.9300
C5—C6	1.360 (10)
C18—S1—C17	91.7 (3)	C10—C11—C12	111.7 (7)
C23—N2—C24	123.1 (5)	H11A—C11—H11B	107.9
C17—N2—C23	114.8 (5)	C12—C11—H11A	109.3
C17—N2—C24	122.1 (6)	C12—C11—H11B	109.3
C9—N1—C10	123.0 (6)	C5—C6—H6	120.1
C1—N1—C9	118.1 (6)	C5—C6—C7	119.9 (7)
C1—N1—C10	118.9 (6)	C7—C6—H6	120.1
N2—C23—C18	112.7 (6)	N2—C24—H24A	109.5
N2—C23—C22	127.5 (6)	N2—C24—H24B	109.5
C18—C23—C22	119.8 (7)	N2—C24—H24C	109.5
C9—C4—C3	119.4 (6)	H24A—C24—H24B	109.5
C5—C4—C3	125.1 (6)	H24A—C24—H24C	109.5
C5—C4—C9	115.5 (7)	H24B—C24—H24C	109.5
C3—C16—H16	115.1	C9—C8—H8	119.5
C17—C16—H16	115.1	C7—C8—C9	121.1 (7)
C17—C16—C3	129.9 (6)	C7—C8—H8	119.5
C16—C3—C4	119.3 (6)	H1A—O1—H1B	109.5
C2—C3—C4	115.6 (6)	C18—C19—H19	121.0
C2—C3—C16	125.1 (7)	C20—C19—C18	118.1 (7)
N2—C17—S1	110.0 (5)	C20—C19—H19	121.0
N2—C17—C16	123.3 (6)	C11—C12—H12A	108.9
C16—C17—S1	126.8 (5)	C11—C12—H12B	108.9
N1—C9—C4	120.7 (7)	H12A—C12—H12B	107.7
N1—C9—C8	119.7 (6)	C13—C12—C11	113.6 (7)
C8—C9—C4	119.6 (6)	C13—C12—H12A	108.9
C3—C2—H2	118.8	C13—C12—H12B	108.9
C1—C2—C3	122.4 (7)	C19—C20—H20	118.8
C1—C2—H2	118.8	C21—C20—C19	122.4 (8)
N1—C1—C2	123.8 (7)	C21—C20—H20	118.8
N1—C1—H1	118.1	C22—C21—H21	119.6
C2—C1—H1	118.1	C20—C21—C22	120.7 (8)
C23—C18—S1	110.8 (5)	C20—C21—H21	119.6
C23—C18—C19	120.8 (7)	C6—C7—H7	120.0
C19—C18—S1	128.3 (5)	C8—C7—C6	120.0 (8)
C23—C22—H22	120.9	C8—C7—H7	120.0
C21—C22—C23	118.2 (7)	C12—C13—H13A	108.3
C21—C22—H22	120.9	C12—C13—H13B	108.3
N1—C10—H10A	108.6	C12—C13—C14	116.0 (9)
N1—C10—H10B	108.6	H13A—C13—H13B	107.4
N1—C10—C11	114.8 (6)	C14—C13—H13A	108.3
H10A—C10—H10B	107.5	C14—C13—H13B	108.3
C11—C10—H10A	108.6	C13—C14—H14	114.1
C11—C10—H10B	108.6	C15—C14—C13	131.8 (13)
C4—C5—H5	118.1	C15—C14—H14	114.1
C6—C5—C4	123.9 (7)	C14—C15—H15A	120.0
C6—C5—H5	118.1	C14—C15—H15B	120.0
C10—C11—H11A	109.3	H15A—C15—H15B	120.0
C10—C11—H11B	109.3
S1—C18—C19—C20	178.2 (6)	C9—C4—C3—C2	−1.0 (10)
N2—C23—C18—S1	1.5 (8)	C9—C4—C5—C6	−1.9 (12)
N2—C23—C18—C19	−178.5 (6)	C9—C8—C7—C6	1.7 (14)
N2—C23—C22—C21	−179.8 (7)	C1—N1—C9—C4	0.6 (10)
N1—C9—C8—C7	178.2 (7)	C1—N1—C9—C8	−179.7 (6)
N1—C10—C11—C12	−174.8 (6)	C1—N1—C10—C11	104.1 (8)
C23—N2—C17—S1	1.7 (7)	C18—S1—C17—N2	−0.7 (5)
C23—N2—C17—C16	−178.1 (6)	C18—S1—C17—C16	179.2 (6)
C23—C18—C19—C20	−1.7 (12)	C18—C23—C22—C21	1.0 (11)
C23—C22—C21—C20	−1.9 (12)	C18—C19—C20—C21	0.8 (14)
C4—C3—C2—C1	−1.1 (11)	C22—C23—C18—S1	−179.1 (5)
C4—C9—C8—C7	−2.1 (12)	C22—C23—C18—C19	0.8 (11)
C4—C5—C6—C7	1.6 (13)	C10—N1—C9—C4	−178.9 (6)
C16—C3—C2—C1	−179.3 (7)	C10—N1—C9—C8	0.8 (11)
C3—C4—C9—N1	1.2 (10)	C10—N1—C1—C2	176.7 (7)
C3—C4—C9—C8	−178.5 (7)	C10—C11—C12—C13	180.0 (8)
C3—C4—C5—C6	178.7 (7)	C5—C4—C3—C16	−3.2 (11)
C3—C16—C17—S1	1.7 (11)	C5—C4—C3—C2	178.4 (7)
C3—C16—C17—N2	−178.5 (7)	C5—C4—C9—N1	−178.2 (6)
C3—C2—C1—N1	3.1 (12)	C5—C4—C9—C8	2.1 (10)
C17—S1—C18—C23	−0.5 (6)	C5—C6—C7—C8	−1.4 (14)
C17—S1—C18—C19	179.6 (7)	C11—C12—C13—C14	−175.8 (9)
C17—N2—C23—C18	−2.1 (8)	C24—N2—C23—C18	178.8 (6)
C17—N2—C23—C22	178.6 (7)	C24—N2—C23—C22	−0.5 (11)
C17—C16—C3—C4	−178.6 (7)	C24—N2—C17—S1	−179.2 (5)
C17—C16—C3—C2	−0.3 (12)	C24—N2—C17—C16	1.0 (10)
C9—N1—C1—C2	−2.8 (11)	C19—C20—C21—C22	1.0 (14)
C9—N1—C10—C11	−76.4 (9)	C12—C13—C14—C15	3 (2)
C9—C4—C3—C16	177.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···S1	0.93	2.40	3.128 (7)	135
O1—H1A···N1	0.85	2.39	3.014 (10)	131
O1—H1B···I1	0.85	2.71	3.546 (10)	169