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The title compound, C18H17NOS, (2), is the product of substitution at the methyl group, in the 2-position of 2,5-di­methyl-4-phenyl­thia­zole, with benz­aldehyde. Molecules of (2) form extended chains through O—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017446/lh6096sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017446/lh60962sup2.hkl
Contains datablock 2

CCDC reference: 222860

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.116
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ..... 0.96
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The metallation of 2,5-dimethyl-4-phenylthiazole by butyllithium can generate anionic methyl groups at positions 2 and 5. The title structure, (2), is the product metallation and the subsequent reaction of the anion with benzaldehyde and was prepared in according to the Scheme below.

The 5-membered heterocycle (S1/C2/N3/C4/C5) is nearly planar and there is conjugation between it and the phenyl ring (C6–C11), the dihedral angle being 6.83 (11)°. The O13–H131···N3 intermolecular hydrogen bond [H131···N3i = 1.96 (4) Å, O13···N3i = 2.831 (2) Å and O13–H131···N3i = 179 (3)°; symmetry code: (i) x, 1/2 − y, z − 1/2] links the molecules in the crystal into extended chains.

Experimental top

Solvents were dried and distilled under an inert atmosphere. The starting thiazole, (1), was prepared from thioacetamide and 2-bromo-1-phenylpropanone using th procedure of Hantch (1889). The reaction was carried out under an inert atmosphere (dry Argon). The 1H NMR spectrum of (2) was recorded on a Bruker AMX-400. The melting point was determined on a hot-stage Boëtius apparatus. BuLi in C6H14 (6 ml, 1.6 M solution) was added to a solution of thiazole (1) (1 g, 5.3 mmol) in 20 ml Et2O/4 ml C4H8O for 10 min at 203 K (dry CO2/C6H6). Benzaldehyde (0.67 g, 6 mmol) in 2 ml of C4H8O was added dropwise to the reaction mixture after 30 min of stirring at 203 K. Then 10 ml of 1 M aqueous citric acid was added after 30 min of stirring and the reaction mixture was left to warm to room temperature, then it was washed with water and brine, dried under Na2SO4 and filtered. Solvent was evaporated in vacuo and 20 ml of C6H14 was added to the resulting yellow oil, after 15 min of heating the mixture was cooled, yielding 0.5 g (60%) of a white precipitate. The product was recrystallized from CH2Cl2/C6H14, m.p. 363–365 K. 1H NMR (CDCl3, 400 MHz, p.p.m.): 7.64 (d, 2H, Ph), 7.43 (t, 4H, Ph), 7,35 (t, 3H, Ph), 7.28 (d, 1H, Ph), 5.19 (dd, 1H, CH), 3.30 (dd, 1H, CH2, J = 4.5 MHz), 3.25 (dd, 1H, CH2, J = 8.5 MHz), 2.53 (s, 3H, CH3).

Refinement top

The hydroxyl H atom was refined isotropically to give an O—H bond length of 0.87 (3) Å. H atoms bonded to C atoms were included in calculated positions and included in the refinement in riding-motion approximation (C—H = 0.93–0.98 Å), with Uiso = 1.2Ueq (1.5Ueq for methyl) of the carrier atom.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 2003) and PLUTON97 (Spek, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 2003).

Figures top
[Figure 1] Fig. 1. ORTEP-3 (Farrugia, 2003) plot of the molecule of title compound. Displacement ellipsoids are shown at the 30% probability level and H atoms asr shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. PLUTON97 (Spek, 1997) packing diagram with the hydrogen-bond scheme shown with dashed lines.
2-(5-Methyl-4-phenyl-1,3-thiazol-2-yl)-1-phenylethanol top
Crystal data top
C18H17NOSF(000) = 624
Mr = 295.39Dx = 1.292 Mg m3
Monoclinic, P21/cMelting point = 363–365 K
Hall symbol: -P 2ybcCu Kα radiation, λ = 1.54180 Å
a = 6.2820 (9) ÅCell parameters from 25 reflections
b = 28.836 (4) Åθ = 33–35°
c = 8.4583 (13) ŵ = 1.86 mm1
β = 97.56 (1)°T = 293 K
V = 1518.9 (4) Å3Prism, colourless
Z = 40.30 × 0.30 × 0.30 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.021
Radiation source: fine-focus sealed tubeθmax = 74.9°, θmin = 3.1°
Graphite monochromatorh = 77
non–profiled ω/2θ scansk = 036
3201 measured reflectionsl = 09
2997 independent reflections1 standard reflections every 226 reflections
2613 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: mixed
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0712P)2 + 0.2241P]
where P = (Fo2 + 2Fc2)/3
2997 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C18H17NOSV = 1518.9 (4) Å3
Mr = 295.39Z = 4
Monoclinic, P21/cCu Kα radiation
a = 6.2820 (9) ŵ = 1.86 mm1
b = 28.836 (4) ÅT = 293 K
c = 8.4583 (13) Å0.30 × 0.30 × 0.30 mm
β = 97.56 (1)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.021
3201 measured reflections1 standard reflections every 226 reflections
2997 independent reflections intensity decay: 2%
2613 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.31 e Å3
2997 reflectionsΔρmin = 0.28 e Å3
195 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.19563 (7)0.255774 (14)0.65532 (5)0.04718 (15)
C20.0259 (3)0.24689 (5)0.74978 (19)0.0427 (3)
N30.0604 (2)0.20369 (4)0.78171 (15)0.0437 (3)
C40.0931 (3)0.17445 (5)0.72955 (18)0.0416 (3)
C50.2457 (3)0.19688 (6)0.65539 (19)0.0446 (4)
C510.4275 (3)0.18051 (7)0.5717 (3)0.0624 (5)
H51A0.53720.16720.64800.094*
H51B0.48580.20630.51980.094*
H51C0.37600.15760.49380.094*
C60.0732 (3)0.12400 (6)0.7571 (2)0.0469 (4)
C70.2287 (4)0.09247 (7)0.7252 (3)0.0769 (7)
H70.35130.10300.68580.092*
C80.2042 (5)0.04542 (8)0.7512 (4)0.0927 (8)
H80.31080.02490.72920.111*
C90.0251 (5)0.02857 (7)0.8090 (3)0.0785 (7)
H90.00810.00310.82390.094*
C100.1288 (4)0.05941 (7)0.8445 (3)0.0697 (6)
H100.24920.04860.88610.084*
C110.1059 (3)0.10649 (6)0.8187 (2)0.0548 (4)
H110.21200.12680.84290.066*
C120.1643 (3)0.28628 (6)0.7933 (2)0.0487 (4)
H12A0.09350.30140.88830.058*
H12B0.29950.27390.81820.058*
C130.2100 (3)0.32240 (5)0.65984 (18)0.0430 (3)
H130.07310.33340.63010.052*
O130.3284 (2)0.30059 (4)0.52548 (15)0.0536 (3)
H1310.245 (5)0.2997 (11)0.451 (4)0.120 (11)*
C140.3319 (3)0.36340 (5)0.71575 (19)0.0435 (4)
C150.2379 (3)0.39113 (6)0.8397 (2)0.0563 (4)
H150.09850.38500.88690.068*
C160.3506 (4)0.42802 (6)0.8939 (3)0.0681 (6)
H160.28730.44610.97820.082*
C170.5552 (4)0.43789 (7)0.8236 (3)0.0726 (6)
H170.63020.46270.85990.087*
C180.6485 (4)0.41098 (7)0.6993 (3)0.0700 (6)
H180.78670.41770.65110.084*
C190.5378 (3)0.37382 (6)0.6453 (2)0.0542 (4)
H190.60240.35580.56120.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0458 (2)0.0460 (2)0.0502 (3)0.00075 (15)0.00793 (17)0.00383 (15)
C20.0485 (9)0.0444 (8)0.0350 (8)0.0036 (6)0.0053 (6)0.0006 (6)
N30.0491 (8)0.0443 (7)0.0382 (7)0.0037 (5)0.0073 (5)0.0024 (5)
C40.0434 (8)0.0445 (8)0.0353 (8)0.0032 (6)0.0014 (6)0.0013 (6)
C50.0389 (8)0.0483 (8)0.0459 (9)0.0036 (6)0.0028 (6)0.0004 (6)
C510.0518 (11)0.0669 (11)0.0716 (13)0.0124 (8)0.0198 (9)0.0054 (9)
C60.0538 (9)0.0433 (8)0.0415 (9)0.0008 (7)0.0021 (7)0.0014 (6)
C70.0830 (16)0.0504 (11)0.1026 (18)0.0092 (10)0.0316 (13)0.0003 (11)
C80.112 (2)0.0480 (11)0.121 (2)0.0168 (12)0.0294 (18)0.0004 (12)
C90.1070 (19)0.0427 (10)0.0818 (16)0.0022 (11)0.0028 (13)0.0043 (9)
C100.0777 (14)0.0571 (11)0.0712 (14)0.0136 (10)0.0019 (11)0.0117 (9)
C110.0567 (11)0.0521 (9)0.0538 (11)0.0023 (8)0.0009 (8)0.0040 (7)
C120.0601 (10)0.0460 (8)0.0415 (9)0.0098 (7)0.0118 (7)0.0033 (6)
C130.0443 (8)0.0465 (8)0.0380 (8)0.0002 (6)0.0053 (6)0.0010 (6)
O130.0552 (7)0.0640 (7)0.0415 (7)0.0000 (6)0.0058 (5)0.0089 (5)
C140.0515 (9)0.0414 (7)0.0379 (9)0.0009 (6)0.0072 (6)0.0057 (6)
C150.0660 (12)0.0471 (9)0.0536 (11)0.0001 (8)0.0005 (8)0.0018 (7)
C160.0993 (17)0.0458 (9)0.0575 (12)0.0015 (10)0.0041 (11)0.0067 (8)
C170.0948 (17)0.0489 (10)0.0765 (15)0.0208 (10)0.0198 (12)0.0010 (9)
C180.0676 (13)0.0589 (11)0.0825 (15)0.0205 (10)0.0057 (11)0.0048 (10)
C190.0551 (10)0.0500 (9)0.0554 (11)0.0067 (7)0.0007 (8)0.0025 (7)
Geometric parameters (Å, º) top
S1—C21.7126 (17)C10—H100.9300
S1—C51.7270 (16)C11—H110.9300
C2—N31.299 (2)C12—C131.535 (2)
C2—C121.505 (2)C12—H12A0.9700
N3—C41.395 (2)C12—H12B0.9700
C4—C51.375 (2)C13—O131.4203 (19)
C4—C61.481 (2)C13—C141.517 (2)
C5—C511.497 (2)C13—H130.9800
C51—H51A0.9600O13—H1310.87 (3)
C51—H51B0.9600C14—C191.385 (2)
C51—H51C0.9600C14—C151.388 (2)
C6—C71.387 (3)C15—C161.389 (3)
C6—C111.395 (3)C15—H150.9300
C7—C81.386 (3)C16—C171.373 (4)
C7—H70.9300C16—H160.9300
C8—C91.373 (4)C17—C181.375 (3)
C8—H80.9300C17—H170.9300
C9—C101.375 (4)C18—C191.387 (3)
C9—H90.9300C18—H180.9300
C10—C111.385 (3)C19—H190.9300
C2—S1—C590.68 (8)C10—C11—H11119.4
N3—C2—C12123.73 (15)C6—C11—H11119.4
N3—C2—S1114.11 (12)C2—C12—C13112.99 (13)
C12—C2—S1122.16 (12)C2—C12—H12A109.0
C2—N3—C4111.88 (14)C13—C12—H12A109.0
C5—C4—N3114.35 (14)C2—C12—H12B109.0
C5—C4—C6127.76 (15)C13—C12—H12B109.0
N3—C4—C6117.89 (15)H12A—C12—H12B107.8
C4—C5—C51133.52 (16)O13—C13—C14111.21 (13)
C4—C5—S1108.97 (12)O13—C13—C12108.40 (13)
C51—C5—S1117.41 (13)C14—C13—C12110.66 (12)
C5—C51—H51A109.5O13—C13—H13108.8
C5—C51—H51B109.5C14—C13—H13108.8
H51A—C51—H51B109.5C12—C13—H13108.8
C5—C51—H51C109.5C13—O13—H131107 (2)
H51A—C51—H51C109.5C19—C14—C15118.74 (16)
H51B—C51—H51C109.5C19—C14—C13121.07 (15)
C7—C6—C11117.30 (17)C15—C14—C13120.19 (15)
C7—C6—C4122.51 (17)C14—C15—C16120.40 (19)
C11—C6—C4120.19 (16)C14—C15—H15119.8
C8—C7—C6121.0 (2)C16—C15—H15119.8
C8—C7—H7119.5C17—C16—C15120.3 (2)
C6—C7—H7119.5C17—C16—H16119.8
C9—C8—C7121.1 (2)C15—C16—H16119.8
C9—C8—H8119.5C16—C17—C18119.68 (19)
C7—C8—H8119.5C16—C17—H17120.2
C8—C9—C10118.8 (2)C18—C17—H17120.2
C8—C9—H9120.6C17—C18—C19120.4 (2)
C10—C9—H9120.6C17—C18—H18119.8
C9—C10—C11120.6 (2)C19—C18—H18119.8
C9—C10—H10119.7C14—C19—C18120.43 (19)
C11—C10—H10119.7C14—C19—H19119.8
C10—C11—C6121.2 (2)C18—C19—H19119.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H131···N3i0.87 (4)1.96 (4)2.831 (2)179 (3)
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC18H17NOS
Mr295.39
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)6.2820 (9), 28.836 (4), 8.4583 (13)
β (°) 97.56 (1)
V3)1518.9 (4)
Z4
Radiation typeCu Kα
µ (mm1)1.86
Crystal size (mm)0.30 × 0.30 × 0.30
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3201, 2997, 2613
Rint0.021
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.116, 1.05
No. of reflections2997
No. of parameters195
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.31, 0.28

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 2003) and PLUTON97 (Spek, 1997), WinGX publication routines (Farrugia, 2003).

Selected geometric parameters (Å, º) top
S1—C21.7126 (17)C9—C101.375 (4)
S1—C51.7270 (16)C10—C111.385 (3)
C2—N31.299 (2)C12—C131.535 (2)
C2—C121.505 (2)C13—O131.4203 (19)
N3—C41.395 (2)C13—C141.517 (2)
C4—C51.375 (2)O13—H1310.87 (3)
C4—C61.481 (2)C14—C191.385 (2)
C5—C511.497 (2)C14—C151.388 (2)
C6—C71.387 (3)C15—C161.389 (3)
C6—C111.395 (3)C16—C171.373 (4)
C7—C81.386 (3)C17—C181.375 (3)
C8—C91.373 (4)C18—C191.387 (3)
C2—S1—C590.68 (8)C8—C9—C10118.8 (2)
N3—C2—C12123.73 (15)C9—C10—C11120.6 (2)
N3—C2—S1114.11 (12)C10—C11—C6121.2 (2)
C12—C2—S1122.16 (12)C2—C12—C13112.99 (13)
C2—N3—C4111.88 (14)O13—C13—C14111.21 (13)
C5—C4—N3114.35 (14)O13—C13—C12108.40 (13)
C5—C4—C6127.76 (15)C14—C13—C12110.66 (12)
N3—C4—C6117.89 (15)C13—O13—H131107 (2)
C4—C5—C51133.52 (16)C19—C14—C15118.74 (16)
C4—C5—S1108.97 (12)C19—C14—C13121.07 (15)
C51—C5—S1117.41 (13)C15—C14—C13120.19 (15)
C7—C6—C11117.30 (17)C14—C15—C16120.40 (19)
C7—C6—C4122.51 (17)C17—C16—C15120.3 (2)
C11—C6—C4120.19 (16)C16—C17—C18119.68 (19)
C8—C7—C6121.0 (2)C17—C18—C19120.4 (2)
C9—C8—C7121.1 (2)C14—C19—C18120.43 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H131···N3i0.87 (4)1.96 (4)2.831 (2)179 (3)
Symmetry code: (i) x, y+1/2, z1/2.
 

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