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In the title compound, C16H12N4S, the dihedral angles formed by the phenyl and the 3H-imidazo[4,5-b]pyridine ring systems with the thia­zole ring are 9.14 (3) and 75.79 (6)°, respectively. There are some intra- and inter­molecular hydrogen-bond inter­actions in the crystal structure, providing stabilization.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503895X/rz6146sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680503895X/rz6146Isup2.hkl
Contains datablock I

CCDC reference: 296640

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.064
  • wR factor = 0.146
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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

Recently, (3H-imidazo[4,5-b]pyridine)(4-phenylthiazol-2-yl)methane and its derivatives have been the focus of increasing attention due to their bioactivities, such as antituberculotic (Bukowski, 2001), anticonvulsant (Tomczuk et al., 1991), anxiolytic (Tomczuk et al., 1991), and antiproliferative activity (Liszkiewicz et al., 2003). These compounds are also employed as ligands (Abbotto et al., 2002). In this paper, we report the crystal structure of the title compound, (I).

Bond lengths and angles of the 3H-imidazo[4,5-b]pyridine and thiazole moieties (Table 1) are in agreement with the values quoted in previous reports (Rodier et al., 1993; Rodriguez et al., 2003). The dihedral angles formed by the phenyl (C3–C8) and the 3H-imidazo[4,5-b]pyridine (N1/N2/N3/C11–C16) rings with the thiazole (S1/N4/C1/C2/C9) ring are 9.14 (3) and 75.79 (6)°, respectively. The crystal structure is stabilized by intra- and intermolecular hydrogen-bond interactions (Table 2 and Fig. 2).

Experimental top

Ethyl 2-(4-phenylthiazol-2-yl)acetate (10 mmol) and 2,3-diaminepyridine (10 mmol) were mixed and reacted at 453–473 K under solvent-free conditions for 1 h. Purification was achieved by recrystallization from methanol (yield 90%). Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a methanol solution at room temperature for two weeks.

Refinement top

All H atoms were placed in calculated positions, with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(carrier atom).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 40% probability level.
[Figure 2] Fig. 2. A packing diagram of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines.
2-[(4,5-Dihydro-4-phenylthiazol-2-yl)methyl]-3H-imidazo[4,5-b]pyridine top
Crystal data top
C16H12N4SF(000) = 608
Mr = 292.37Dx = 1.375 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb cCell parameters from 2273 reflections
a = 12.685 (6) Åθ = 2.3–26.3°
b = 5.277 (2) ŵ = 0.23 mm1
c = 21.389 (9) ÅT = 293 K
β = 100.577 (6)°Block, colourless
V = 1407.5 (11) Å30.35 × 0.21 × 0.12 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2509 independent reflections
Radiation source: fine-focus sealed tube2210 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ϕ and ω scansθmax = 25.2°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.925, Tmax = 0.973k = 56
6901 measured reflectionsl = 2325
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.18 w = 1/[σ2(Fo2) + (0.0481P)2 + 0.6991P]
where P = (Fo2 + 2Fc2)/3
2509 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C16H12N4SV = 1407.5 (11) Å3
Mr = 292.37Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.685 (6) ŵ = 0.23 mm1
b = 5.277 (2) ÅT = 293 K
c = 21.389 (9) Å0.35 × 0.21 × 0.12 mm
β = 100.577 (6)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2509 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2210 reflections with I > 2σ(I)
Tmin = 0.925, Tmax = 0.973Rint = 0.030
6901 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 1.18Δρmax = 0.29 e Å3
2509 reflectionsΔρmin = 0.23 e Å3
190 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
C10.1685 (3)0.8913 (7)0.26545 (17)0.0755 (10)
H10.11381.00310.24870.091*
C20.1624 (2)0.7222 (5)0.31194 (13)0.0522 (7)
C30.0710 (2)0.6865 (5)0.34458 (14)0.0544 (7)
C40.0146 (3)0.8553 (7)0.33510 (18)0.0744 (9)
H40.01400.99160.30760.089*
C50.0998 (3)0.8247 (8)0.3655 (2)0.0902 (12)
H50.15620.93990.35830.108*
C60.1028 (3)0.6277 (9)0.4061 (2)0.0906 (13)
H60.16040.60920.42700.109*
C70.0198 (3)0.4561 (8)0.41601 (18)0.0843 (11)
H70.02190.31980.44330.101*
C80.0672 (3)0.4851 (6)0.38532 (16)0.0676 (9)
H80.12300.36830.39230.081*
C90.3258 (2)0.6338 (5)0.29560 (12)0.0516 (7)
C100.4368 (2)0.5263 (6)0.30625 (13)0.0539 (7)
H10A0.43450.34800.31700.065*
H10B0.46600.54080.26750.065*
C110.5075 (2)0.6648 (5)0.35901 (12)0.0453 (6)
C120.6145 (2)0.9257 (5)0.41357 (12)0.0472 (6)
C130.6856 (2)1.1145 (6)0.43829 (15)0.0620 (8)
H130.71261.22900.41210.074*
C140.7149 (2)1.1247 (6)0.50388 (16)0.0640 (8)
H140.76281.24820.52250.077*
C150.6737 (2)0.9539 (6)0.54187 (15)0.0598 (8)
H150.69600.96680.58570.072*
C160.57800 (19)0.7653 (5)0.45649 (12)0.0423 (6)
N10.60379 (19)0.7707 (4)0.51977 (10)0.0544 (6)
N20.50912 (17)0.6000 (4)0.42027 (10)0.0459 (5)
H2A0.47390.47890.43380.055*
N30.56817 (18)0.8587 (5)0.35167 (10)0.0550 (6)
N40.25349 (18)0.5744 (4)0.32886 (10)0.0494 (6)
S10.28866 (7)0.8740 (2)0.24127 (4)0.0814 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0591 (19)0.081 (2)0.079 (2)0.0044 (17)0.0079 (16)0.0262 (19)
C20.0488 (16)0.0523 (16)0.0493 (16)0.0066 (13)0.0074 (12)0.0074 (13)
C30.0515 (16)0.0515 (16)0.0551 (17)0.0100 (13)0.0035 (13)0.0135 (14)
C40.069 (2)0.066 (2)0.088 (3)0.0012 (17)0.0126 (19)0.0129 (18)
C50.072 (2)0.080 (3)0.122 (3)0.001 (2)0.026 (2)0.025 (3)
C60.075 (3)0.095 (3)0.110 (3)0.021 (2)0.037 (2)0.040 (3)
C70.094 (3)0.082 (3)0.081 (3)0.029 (2)0.028 (2)0.011 (2)
C80.065 (2)0.069 (2)0.067 (2)0.0070 (16)0.0073 (16)0.0067 (17)
C90.0530 (16)0.0597 (17)0.0384 (14)0.0080 (14)0.0018 (12)0.0080 (13)
C100.0553 (17)0.0653 (18)0.0402 (14)0.0001 (14)0.0063 (12)0.0077 (13)
C110.0410 (14)0.0571 (16)0.0376 (14)0.0050 (12)0.0071 (11)0.0037 (12)
C120.0384 (14)0.0576 (17)0.0464 (15)0.0013 (12)0.0101 (11)0.0007 (13)
C130.0541 (17)0.0660 (19)0.067 (2)0.0117 (15)0.0131 (15)0.0003 (16)
C140.0539 (18)0.0622 (19)0.072 (2)0.0121 (15)0.0000 (15)0.0138 (16)
C150.0601 (18)0.0624 (18)0.0507 (17)0.0004 (15)0.0062 (14)0.0105 (15)
C160.0386 (13)0.0464 (14)0.0404 (14)0.0057 (11)0.0029 (11)0.0037 (11)
N10.0626 (15)0.0556 (14)0.0411 (13)0.0022 (12)0.0010 (11)0.0036 (11)
N20.0496 (13)0.0467 (12)0.0404 (12)0.0056 (10)0.0051 (9)0.0001 (10)
N30.0537 (14)0.0690 (16)0.0425 (13)0.0065 (12)0.0096 (10)0.0018 (11)
N40.0543 (14)0.0501 (13)0.0403 (12)0.0022 (11)0.0003 (10)0.0053 (10)
S10.0651 (6)0.1034 (8)0.0730 (6)0.0009 (5)0.0056 (4)0.0362 (5)
Geometric parameters (Å, º) top
C1—C21.349 (4)C9—S11.725 (3)
C1—S11.700 (4)C10—C111.497 (4)
C1—H10.9300C10—H10A0.9700
C2—N41.386 (3)C10—H10B0.9700
C2—C31.471 (4)C11—N31.307 (3)
C3—C81.381 (4)C11—N21.351 (3)
C3—C41.390 (4)C12—C131.382 (4)
C4—C51.370 (5)C12—C161.389 (4)
C4—H40.9300C12—N31.392 (3)
C5—C61.360 (6)C13—C141.385 (4)
C5—H50.9300C13—H130.9300
C6—C71.375 (5)C14—C151.379 (4)
C6—H60.9300C14—H140.9300
C7—C81.392 (5)C15—N11.338 (4)
C7—H70.9300C15—H150.9300
C8—H80.9300C16—N11.333 (3)
C9—N41.298 (3)C16—N21.370 (3)
C9—C101.497 (4)N2—H2A0.8600
C2—C1—S1111.4 (2)C9—C10—H10A109.6
C2—C1—H1124.3C11—C10—H10B109.6
S1—C1—H1124.3C9—C10—H10B109.6
C1—C2—N4114.0 (3)H10A—C10—H10B108.1
C1—C2—C3126.2 (3)N3—C11—N2114.2 (2)
N4—C2—C3119.7 (3)N3—C11—C10125.2 (2)
C8—C3—C4117.9 (3)N2—C11—C10120.5 (2)
C8—C3—C2121.3 (3)C13—C12—C16117.4 (2)
C4—C3—C2120.7 (3)C13—C12—N3132.8 (3)
C5—C4—C3121.2 (4)C16—C12—N3109.9 (2)
C5—C4—H4119.4C12—C13—C14116.8 (3)
C3—C4—H4119.4C12—C13—H13121.6
C6—C5—C4120.7 (4)C14—C13—H13121.6
C6—C5—H5119.6C15—C14—C13120.8 (3)
C4—C5—H5119.6C15—C14—H14119.6
C5—C6—C7119.5 (4)C13—C14—H14119.6
C5—C6—H6120.3N1—C15—C14124.2 (3)
C7—C6—H6120.3N1—C15—H15117.9
C6—C7—C8120.4 (4)C14—C15—H15117.9
C6—C7—H7119.8N1—C16—N2126.9 (2)
C8—C7—H7119.8N1—C16—C12127.5 (2)
C3—C8—C7120.3 (3)N2—C16—C12105.6 (2)
C3—C8—H8119.8C16—N1—C15113.4 (2)
C7—C8—H8119.8C11—N2—C16106.4 (2)
N4—C9—C10124.4 (3)C11—N2—H2A126.8
N4—C9—S1114.4 (2)C16—N2—H2A126.8
C10—C9—S1120.9 (2)C11—N3—C12103.9 (2)
C11—C10—C9110.3 (2)C9—N4—C2111.1 (2)
C11—C10—H10A109.6C1—S1—C989.08 (15)
S1—C1—C2—N40.4 (4)C13—C12—C16—N10.2 (4)
S1—C1—C2—C3179.2 (2)N3—C12—C16—N1179.6 (2)
C1—C2—C3—C8171.0 (3)C13—C12—C16—N2179.5 (2)
N4—C2—C3—C89.5 (4)N3—C12—C16—N20.1 (3)
C1—C2—C3—C48.9 (4)N2—C16—N1—C15179.8 (3)
N4—C2—C3—C4170.7 (3)C12—C16—N1—C150.6 (4)
C8—C3—C4—C50.5 (5)C14—C15—N1—C160.9 (4)
C2—C3—C4—C5179.6 (3)N3—C11—N2—C160.6 (3)
C3—C4—C5—C60.2 (6)C10—C11—N2—C16178.0 (2)
C4—C5—C6—C70.8 (6)N1—C16—N2—C11180.0 (2)
C5—C6—C7—C80.8 (6)C12—C16—N2—C110.3 (3)
C4—C3—C8—C70.6 (4)N2—C11—N3—C120.6 (3)
C2—C3—C8—C7179.6 (3)C10—C11—N3—C12177.9 (2)
C6—C7—C8—C30.1 (5)C13—C12—N3—C11179.7 (3)
N4—C9—C10—C1182.2 (3)C16—C12—N3—C110.4 (3)
S1—C9—C10—C1191.6 (3)C10—C9—N4—C2174.2 (2)
C9—C10—C11—N393.2 (3)S1—C9—N4—C20.0 (3)
C9—C10—C11—N283.9 (3)C1—C2—N4—C90.2 (3)
C16—C12—C13—C140.6 (4)C3—C2—N4—C9179.4 (2)
N3—C12—C13—C14179.9 (3)C2—C1—S1—C90.3 (3)
C12—C13—C14—C150.3 (5)N4—C9—S1—C10.2 (2)
C13—C14—C15—N10.5 (5)C10—C9—S1—C1174.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N1i0.862.012.863 (3)170
C8—H8···N40.932.572.884 (4)100
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC16H12N4S
Mr292.37
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.685 (6), 5.277 (2), 21.389 (9)
β (°) 100.577 (6)
V3)1407.5 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.35 × 0.21 × 0.12
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.925, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections
6901, 2509, 2210
Rint0.030
(sin θ/λ)max1)0.598
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.146, 1.18
No. of reflections2509
No. of parameters190
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.23

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Selected geometric parameters (Å, º) top
C1—C21.349 (4)C11—N21.351 (3)
C1—S11.700 (4)C12—N31.392 (3)
C9—N41.298 (3)C15—N11.338 (4)
C9—S11.725 (3)C16—N11.333 (3)
C11—N31.307 (3)C16—N21.370 (3)
C11—C10—C9110.3 (2)C1—S1—C989.08 (15)
C9—N4—C2111.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N1i0.862.012.863 (3)170
C8—H8···N40.932.572.884 (4)100
Symmetry code: (i) x+1, y+1, z+1.
 

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