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The title compound, C20H12N2OS, was synthesized by mixing 2,4-dichloro­benzaldehyde, ethyl chloro­acetate and tetra­hydro­pyrimidine-2-thione in ethanol. The dihedral angle between the naphthalene plane and the heterocyclic ring system is 9.3 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027613/hg6233sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027613/hg6233Isup2.hkl
Contains datablock I

CCDC reference: 287591

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.049
  • wR factor = 0.109
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT410_ALERT_2_C Short Intra H...H Contact H10 .. H19 .. 1.98 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Dihydroimidazoles are reported to exhibit diverse biological and pharmacological properties. Examples of these include vasodepressor, sympathomimetic, antihistaminic, histamine-like and cholinomimetic activity (Gilman & Goodman, 2001; Greenhill & Lue, 1993). Dihydroimidazoles, such as midaglizole, deriglidole and efaroxan, have been found to be potent antihyperglycaemic agents (Bihan et al., 1999). Thus, there has been considerable interest in the chemistry of dihydroimidazole and its derivatives in recent years. In this paper, the structure of the title compound, (I), is reported.

The molecular structure of (I) is illustrated in Fig. 1. The heterocyclic ring system is essentially planar, with a mean deviation of 0.0067 (3) Å. Selected bond lengths and angles are listed in Table 1. Taking account of the different substitution patterns, the geometry of the heterocyclic ring system compares favourably with that in the related compounds (2Z)-2-[(anthracen-9-yl)methylene]-5,6-dihydroimidazo[2,1-b]thiazol-3(2H)-one (Liang & Li, 2005) and 6-(4-chlorobenzylidene)-2,3-dihydroimidazo[2,1-b]thiazol-5(6H)-one (Karolak-Wojciechowska & Kiec-Kononowicz, 1991). The naphthalene ring system is planar to within 0.0135 (3) Å. The dihedral angle between the naphthalene plane and the heterocyclic ring system is 9.3 (3)°.

Experimental top

A mixture of benzo[4,5]imidazo[2,1-b]thiazol-3-one (0.02 mol) and naphthaldehyde (0.02 mol) was stirred under reflux in CH3COONa/CH3COOH solution (40 ml) for 90 min. After cooling and filtration, the title compound was recrystallized from acetic acid. A quantity of (I) (15 mg) was dissolved in trichloromethane (20 ml) and the solution kept at room temperature for 7 d. Slow solvent evaporation gave yellow single crystals of (I) suitable for X-ray analysis (m.p. 486–488 K). Spectroscopic analysis: 1H NMR (Frequency?, Medium?, δ, p.p.m.): 7.27–7.71 (m, 11H, ArH), 7.42 (s, 1H, –CH).

Refinement top

H atoms were positioned geometrically, with C—H = 0.93–0.98 Å, and refined in a riding model, with Uiso(H) = 1.5Ueq(carrier).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Please provide caption.
2-[(Z)-(1-Naphthyl)methylene]benzimidazo[2,1-b]thiazol-3(2H)-one top
Crystal data top
C20H12N2OSF(000) = 680
Mr = 328.38Dx = 1.496 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 894 reflections
a = 6.8627 (16) Åθ = 3.0–25.4°
b = 7.9031 (19) ŵ = 0.23 mm1
c = 27.010 (6) ÅT = 90 K
β = 95.406 (4)°Plate, yellow
V = 1458.4 (6) Å30.04 × 0.04 × 0.01 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3432 independent reflections
Radiation source: fine-focus sealed tube1989 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
ϕ and ω scansθmax = 27.9°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 88
Tmin = 0.980, Tmax = 0.998k = 108
8139 measured reflectionsl = 2835
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049 w = 1/[σ2(Fo2) + (0.0394P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109(Δ/σ)max < 0.001
S = 0.95Δρmax = 0.34 e Å3
3432 reflectionsΔρmin = 0.35 e Å3
217 parameters
Crystal data top
C20H12N2OSV = 1458.4 (6) Å3
Mr = 328.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.8627 (16) ŵ = 0.23 mm1
b = 7.9031 (19) ÅT = 90 K
c = 27.010 (6) Å0.04 × 0.04 × 0.01 mm
β = 95.406 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3432 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
1989 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.998Rint = 0.071
8139 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 0.95Δρmax = 0.34 e Å3
3432 reflectionsΔρmin = 0.35 e Å3
217 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1244 (4)0.3340 (3)0.02914 (9)0.0133 (6)
C20.3138 (4)0.3939 (3)0.03455 (10)0.0157 (5)
H20.40160.37550.00990.019*
C30.3695 (4)0.4823 (3)0.07788 (10)0.0176 (6)
H30.49890.52570.08330.021*
C40.2387 (4)0.5086 (3)0.11379 (10)0.0179 (6)
H40.28110.57100.14290.022*
C50.0492 (4)0.4466 (3)0.10822 (10)0.0175 (6)
H50.03780.46390.13310.021*
C60.0087 (4)0.3581 (3)0.06499 (9)0.0136 (6)
C70.1659 (4)0.2148 (3)0.00776 (9)0.0135 (6)
C80.0527 (4)0.1745 (3)0.05420 (9)0.0138 (6)
C90.1285 (3)0.0860 (3)0.07529 (9)0.0122 (5)
C100.1329 (4)0.0146 (3)0.12013 (9)0.0134 (6)
H100.01300.02170.13490.016*
C110.2890 (4)0.0722 (3)0.15048 (9)0.0147 (6)
C120.4650 (3)0.1119 (3)0.13241 (9)0.0156 (6)
H120.48530.08060.09930.019*
C130.6139 (4)0.1967 (3)0.16119 (10)0.0181 (6)
H130.73300.22210.14750.022*
C140.5897 (4)0.2433 (3)0.20888 (10)0.0187 (6)
H140.69130.30200.22810.022*
C150.4137 (4)0.2045 (3)0.22993 (9)0.0160 (6)
C160.3897 (4)0.2469 (3)0.28003 (10)0.0192 (6)
H160.49240.30410.29930.023*
C170.2235 (4)0.2077 (3)0.30112 (10)0.0200 (6)
H170.21110.23530.33490.024*
C180.0699 (4)0.1259 (3)0.27235 (10)0.0181 (6)
H180.04770.10030.28670.022*
C190.0878 (4)0.0830 (3)0.22412 (9)0.0156 (6)
H190.01790.02720.20560.019*
C200.2595 (4)0.1192 (3)0.20084 (9)0.0139 (6)
N10.1914 (3)0.2805 (3)0.05031 (8)0.0158 (5)
N20.0187 (3)0.2406 (3)0.00826 (7)0.0125 (5)
O10.2052 (2)0.1884 (2)0.07316 (6)0.0177 (4)
S10.31774 (9)0.09958 (8)0.03509 (2)0.01514 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0160 (14)0.0107 (13)0.0126 (13)0.0044 (11)0.0020 (10)0.0005 (11)
C20.0148 (13)0.0133 (13)0.0193 (14)0.0026 (12)0.0026 (10)0.0026 (12)
C30.0159 (14)0.0143 (14)0.0216 (16)0.0001 (11)0.0033 (12)0.0032 (12)
C40.0226 (16)0.0107 (14)0.0194 (15)0.0013 (12)0.0037 (12)0.0043 (11)
C50.0208 (15)0.0153 (14)0.0168 (15)0.0027 (12)0.0025 (11)0.0011 (11)
C60.0149 (14)0.0112 (13)0.0147 (14)0.0011 (11)0.0015 (11)0.0002 (11)
C70.0130 (13)0.0132 (14)0.0141 (14)0.0015 (11)0.0009 (10)0.0009 (11)
C80.0155 (14)0.0124 (14)0.0133 (14)0.0044 (11)0.0003 (11)0.0014 (10)
C90.0100 (13)0.0146 (14)0.0121 (13)0.0022 (11)0.0017 (10)0.0001 (11)
C100.0125 (13)0.0116 (13)0.0164 (14)0.0014 (11)0.0029 (10)0.0045 (11)
C110.0170 (14)0.0123 (14)0.0145 (14)0.0016 (11)0.0007 (11)0.0008 (11)
C120.0170 (14)0.0142 (14)0.0153 (14)0.0005 (12)0.0003 (11)0.0035 (11)
C130.0134 (14)0.0206 (15)0.0204 (15)0.0033 (12)0.0017 (11)0.0013 (12)
C140.0126 (14)0.0176 (15)0.0245 (15)0.0027 (11)0.0058 (11)0.0003 (12)
C150.0160 (14)0.0145 (14)0.0171 (14)0.0017 (11)0.0008 (11)0.0023 (11)
C160.0250 (16)0.0148 (15)0.0167 (15)0.0018 (12)0.0037 (12)0.0016 (11)
C170.0276 (16)0.0188 (15)0.0138 (14)0.0064 (13)0.0026 (12)0.0002 (12)
C180.0157 (14)0.0206 (16)0.0183 (15)0.0005 (12)0.0029 (11)0.0033 (12)
C190.0123 (13)0.0175 (14)0.0162 (14)0.0009 (12)0.0032 (10)0.0009 (12)
C200.0175 (14)0.0097 (14)0.0141 (14)0.0012 (11)0.0011 (10)0.0027 (11)
N10.0129 (12)0.0168 (12)0.0177 (12)0.0011 (10)0.0013 (9)0.0003 (10)
N20.0129 (11)0.0116 (11)0.0130 (12)0.0006 (9)0.0005 (9)0.0007 (9)
O10.0142 (10)0.0227 (11)0.0165 (10)0.0008 (8)0.0021 (8)0.0016 (8)
S10.0125 (3)0.0175 (4)0.0155 (3)0.0014 (3)0.0015 (2)0.0018 (3)
Geometric parameters (Å, º) top
C1—C21.379 (3)C10—C111.458 (3)
C1—N21.397 (3)C10—H100.9500
C1—C61.405 (3)C11—C121.380 (3)
C2—C31.386 (3)C11—C201.442 (3)
C2—H20.9500C12—C131.396 (3)
C3—C41.398 (4)C12—H120.9500
C3—H30.9500C13—C141.365 (4)
C4—C51.385 (3)C13—H130.9500
C4—H40.9500C14—C151.416 (3)
C5—C61.387 (3)C14—H140.9500
C5—H50.9500C15—C161.419 (4)
C6—N11.418 (3)C15—C201.426 (3)
C7—N11.288 (3)C16—C171.358 (4)
C7—N21.392 (3)C16—H160.9500
C7—S11.740 (3)C17—C181.406 (4)
C8—O11.212 (3)C17—H170.9500
C8—N21.386 (3)C18—C191.363 (3)
C8—C91.493 (3)C18—H180.9500
C9—C101.334 (3)C19—C201.416 (3)
C9—S11.773 (2)C19—H190.9500
C2—C1—N2132.7 (2)C11—C12—C13122.1 (2)
C2—C1—C6123.2 (2)C11—C12—H12119.0
N2—C1—C6104.1 (2)C13—C12—H12119.0
C1—C2—C3116.4 (2)C14—C13—C12120.5 (2)
C1—C2—H2121.8C14—C13—H13119.8
C3—C2—H2121.8C12—C13—H13119.8
C2—C3—C4121.2 (2)C13—C14—C15120.3 (2)
C2—C3—H3119.4C13—C14—H14119.8
C4—C3—H3119.4C15—C14—H14119.8
C5—C4—C3122.0 (2)C14—C15—C16120.8 (2)
C5—C4—H4119.0C14—C15—C20119.8 (2)
C3—C4—H4119.0C16—C15—C20119.4 (2)
C4—C5—C6117.5 (2)C17—C16—C15121.6 (2)
C4—C5—H5121.2C17—C16—H16119.2
C6—C5—H5121.2C15—C16—H16119.2
C5—C6—C1119.7 (2)C16—C17—C18119.2 (2)
C5—C6—N1129.0 (2)C16—C17—H17120.4
C1—C6—N1111.3 (2)C18—C17—H17120.4
N1—C7—N2115.0 (2)C19—C18—C17120.8 (2)
N1—C7—S1133.0 (2)C19—C18—H18119.6
N2—C7—S1112.05 (17)C17—C18—H18119.6
O1—C8—N2124.7 (2)C18—C19—C20121.9 (2)
O1—C8—C9127.0 (2)C18—C19—H19119.1
N2—C8—C9108.3 (2)C20—C19—H19119.1
C10—C9—C8119.4 (2)C19—C20—C15117.1 (2)
C10—C9—S1128.8 (2)C19—C20—C11124.3 (2)
C8—C9—S1111.72 (17)C15—C20—C11118.6 (2)
C9—C10—C11131.5 (2)C7—N1—C6103.5 (2)
C9—C10—H10114.3C8—N2—C7117.3 (2)
C11—C10—H10114.3C8—N2—C1136.6 (2)
C12—C11—C20118.7 (2)C7—N2—C1106.1 (2)
C12—C11—C10121.9 (2)C7—S1—C990.68 (12)
C20—C11—C10119.4 (2)
N2—C1—C2—C3179.4 (3)C18—C19—C20—C150.6 (4)
C6—C1—C2—C30.4 (4)C18—C19—C20—C11178.0 (2)
C1—C2—C3—C40.1 (4)C14—C15—C20—C19179.6 (2)
C2—C3—C4—C50.8 (4)C16—C15—C20—C190.6 (3)
C3—C4—C5—C60.9 (4)C14—C15—C20—C110.9 (4)
C4—C5—C6—C10.4 (4)C16—C15—C20—C11178.0 (2)
C4—C5—C6—N1179.3 (2)C12—C11—C20—C19178.7 (2)
C2—C1—C6—C50.3 (4)C10—C11—C20—C191.6 (4)
N2—C1—C6—C5179.5 (2)C12—C11—C20—C150.1 (4)
C2—C1—C6—N1178.8 (2)C10—C11—C20—C15179.8 (2)
N2—C1—C6—N10.4 (3)N2—C7—N1—C60.1 (3)
O1—C8—C9—C101.3 (4)S1—C7—N1—C6179.5 (2)
N2—C8—C9—C10178.6 (2)C5—C6—N1—C7179.2 (3)
O1—C8—C9—S1179.3 (2)C1—C6—N1—C70.2 (3)
N2—C8—C9—S10.7 (3)O1—C8—N2—C7179.2 (2)
C8—C9—C10—C11177.0 (2)C9—C8—N2—C70.7 (3)
S1—C9—C10—C110.5 (4)O1—C8—N2—C10.0 (5)
C9—C10—C11—C128.0 (4)C9—C8—N2—C1179.9 (3)
C9—C10—C11—C20172.3 (3)N1—C7—N2—C8179.1 (2)
C20—C11—C12—C130.4 (4)S1—C7—N2—C80.4 (3)
C10—C11—C12—C13179.3 (2)N1—C7—N2—C10.4 (3)
C11—C12—C13—C140.1 (4)S1—C7—N2—C1179.86 (17)
C12—C13—C14—C150.7 (4)C2—C1—N2—C82.1 (5)
C13—C14—C15—C16177.7 (2)C6—C1—N2—C8178.8 (3)
C13—C14—C15—C201.2 (4)C2—C1—N2—C7178.7 (3)
C14—C15—C16—C17178.7 (2)C6—C1—N2—C70.4 (2)
C20—C15—C16—C170.2 (4)N1—C7—S1—C9179.4 (3)
C15—C16—C17—C181.2 (4)N2—C7—S1—C90.01 (19)
C16—C17—C18—C191.3 (4)C10—C9—S1—C7178.1 (3)
C17—C18—C19—C200.4 (4)C8—C9—S1—C70.40 (19)

Experimental details

Crystal data
Chemical formulaC20H12N2OS
Mr328.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)90
a, b, c (Å)6.8627 (16), 7.9031 (19), 27.010 (6)
β (°) 95.406 (4)
V3)1458.4 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.04 × 0.04 × 0.01
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.980, 0.998
No. of measured, independent and
observed [I > 2σ(I)] reflections
8139, 3432, 1989
Rint0.071
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.109, 0.95
No. of reflections3432
No. of parameters217
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.35

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
C1—N21.397 (3)C8—O11.212 (3)
C1—C61.405 (3)C8—N21.386 (3)
C6—N11.418 (3)C8—C91.493 (3)
C7—N11.288 (3)C9—C101.334 (3)
C7—N21.392 (3)C9—S11.773 (2)
C7—S11.740 (3)
N2—C1—C6104.1 (2)N2—C8—C9108.3 (2)
C1—C6—N1111.3 (2)C8—C9—S1111.72 (17)
N1—C7—N2115.0 (2)C7—N1—C6103.5 (2)
N1—C7—S1133.0 (2)C8—N2—C7117.3 (2)
N2—C7—S1112.05 (17)C8—N2—C1136.6 (2)
O1—C8—N2124.7 (2)C7—N2—C1106.1 (2)
O1—C8—C9127.0 (2)C7—S1—C990.68 (12)
 

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