Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503895X/rz6146sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680503895X/rz6146Isup2.hkl |
CCDC reference: 296640
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
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).
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.
C16H12N4S | F(000) = 608 |
Mr = 292.37 | Dx = 1.375 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yb c | Cell parameters from 2273 reflections |
a = 12.685 (6) Å | θ = 2.3–26.3° |
b = 5.277 (2) Å | µ = 0.23 mm−1 |
c = 21.389 (9) Å | T = 293 K |
β = 100.577 (6)° | Block, colourless |
V = 1407.5 (11) Å3 | 0.35 × 0.21 × 0.12 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2509 independent reflections |
Radiation source: fine-focus sealed tube | 2210 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ϕ and ω scans | θmax = 25.2°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.925, Tmax = 0.973 | k = −5→6 |
6901 measured reflections | l = −23→25 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-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 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C16H12N4S | V = 1407.5 (11) Å3 |
Mr = 292.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.685 (6) Å | µ = 0.23 mm−1 |
b = 5.277 (2) Å | T = 293 K |
c = 21.389 (9) Å | 0.35 × 0.21 × 0.12 mm |
β = 100.577 (6)° |
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 = 0.973 | Rint = 0.030 |
6901 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.18 | Δρmax = 0.29 e Å−3 |
2509 reflections | Δρmin = −0.23 e Å−3 |
190 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.1685 (3) | 0.8913 (7) | 0.26545 (17) | 0.0755 (10) | |
H1 | 0.1138 | 1.0031 | 0.2487 | 0.091* | |
C2 | 0.1624 (2) | 0.7222 (5) | 0.31194 (13) | 0.0522 (7) | |
C3 | 0.0710 (2) | 0.6865 (5) | 0.34458 (14) | 0.0544 (7) | |
C4 | −0.0146 (3) | 0.8553 (7) | 0.33510 (18) | 0.0744 (9) | |
H4 | −0.0140 | 0.9916 | 0.3076 | 0.089* | |
C5 | −0.0998 (3) | 0.8247 (8) | 0.3655 (2) | 0.0902 (12) | |
H5 | −0.1562 | 0.9399 | 0.3583 | 0.108* | |
C6 | −0.1028 (3) | 0.6277 (9) | 0.4061 (2) | 0.0906 (13) | |
H6 | −0.1604 | 0.6092 | 0.4270 | 0.109* | |
C7 | −0.0198 (3) | 0.4561 (8) | 0.41601 (18) | 0.0843 (11) | |
H7 | −0.0219 | 0.3198 | 0.4433 | 0.101* | |
C8 | 0.0672 (3) | 0.4851 (6) | 0.38532 (16) | 0.0676 (9) | |
H8 | 0.1230 | 0.3683 | 0.3923 | 0.081* | |
C9 | 0.3258 (2) | 0.6338 (5) | 0.29560 (12) | 0.0516 (7) | |
C10 | 0.4368 (2) | 0.5263 (6) | 0.30625 (13) | 0.0539 (7) | |
H10A | 0.4345 | 0.3480 | 0.3170 | 0.065* | |
H10B | 0.4660 | 0.5408 | 0.2675 | 0.065* | |
C11 | 0.5075 (2) | 0.6648 (5) | 0.35901 (12) | 0.0453 (6) | |
C12 | 0.6145 (2) | 0.9257 (5) | 0.41357 (12) | 0.0472 (6) | |
C13 | 0.6856 (2) | 1.1145 (6) | 0.43829 (15) | 0.0620 (8) | |
H13 | 0.7126 | 1.2290 | 0.4121 | 0.074* | |
C14 | 0.7149 (2) | 1.1247 (6) | 0.50388 (16) | 0.0640 (8) | |
H14 | 0.7628 | 1.2482 | 0.5225 | 0.077* | |
C15 | 0.6737 (2) | 0.9539 (6) | 0.54187 (15) | 0.0598 (8) | |
H15 | 0.6960 | 0.9668 | 0.5857 | 0.072* | |
C16 | 0.57800 (19) | 0.7653 (5) | 0.45649 (12) | 0.0423 (6) | |
N1 | 0.60379 (19) | 0.7707 (4) | 0.51977 (10) | 0.0544 (6) | |
N2 | 0.50912 (17) | 0.6000 (4) | 0.42027 (10) | 0.0459 (5) | |
H2A | 0.4739 | 0.4789 | 0.4338 | 0.055* | |
N3 | 0.56817 (18) | 0.8587 (5) | 0.35167 (10) | 0.0550 (6) | |
N4 | 0.25349 (18) | 0.5744 (4) | 0.32886 (10) | 0.0494 (6) | |
S1 | 0.28866 (7) | 0.8740 (2) | 0.24127 (4) | 0.0814 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0591 (19) | 0.081 (2) | 0.079 (2) | 0.0044 (17) | −0.0079 (16) | 0.0262 (19) |
C2 | 0.0488 (16) | 0.0523 (16) | 0.0493 (16) | −0.0066 (13) | −0.0074 (12) | −0.0074 (13) |
C3 | 0.0515 (16) | 0.0515 (16) | 0.0551 (17) | −0.0100 (13) | −0.0035 (13) | −0.0135 (14) |
C4 | 0.069 (2) | 0.066 (2) | 0.088 (3) | −0.0012 (17) | 0.0126 (19) | −0.0129 (18) |
C5 | 0.072 (2) | 0.080 (3) | 0.122 (3) | −0.001 (2) | 0.026 (2) | −0.025 (3) |
C6 | 0.075 (3) | 0.095 (3) | 0.110 (3) | −0.021 (2) | 0.037 (2) | −0.040 (3) |
C7 | 0.094 (3) | 0.082 (3) | 0.081 (3) | −0.029 (2) | 0.028 (2) | −0.011 (2) |
C8 | 0.065 (2) | 0.069 (2) | 0.067 (2) | −0.0070 (16) | 0.0073 (16) | −0.0067 (17) |
C9 | 0.0530 (16) | 0.0597 (17) | 0.0384 (14) | −0.0080 (14) | −0.0018 (12) | −0.0080 (13) |
C10 | 0.0553 (17) | 0.0653 (18) | 0.0402 (14) | −0.0001 (14) | 0.0063 (12) | −0.0077 (13) |
C11 | 0.0410 (14) | 0.0571 (16) | 0.0376 (14) | 0.0050 (12) | 0.0071 (11) | −0.0037 (12) |
C12 | 0.0384 (14) | 0.0576 (17) | 0.0464 (15) | 0.0013 (12) | 0.0101 (11) | −0.0007 (13) |
C13 | 0.0541 (17) | 0.0660 (19) | 0.067 (2) | −0.0117 (15) | 0.0131 (15) | −0.0003 (16) |
C14 | 0.0539 (18) | 0.0622 (19) | 0.072 (2) | −0.0121 (15) | 0.0000 (15) | −0.0138 (16) |
C15 | 0.0601 (18) | 0.0624 (18) | 0.0507 (17) | 0.0004 (15) | −0.0062 (14) | −0.0105 (15) |
C16 | 0.0386 (13) | 0.0464 (14) | 0.0404 (14) | 0.0057 (11) | 0.0029 (11) | −0.0037 (11) |
N1 | 0.0626 (15) | 0.0556 (14) | 0.0411 (13) | −0.0022 (12) | −0.0010 (11) | −0.0036 (11) |
N2 | 0.0496 (13) | 0.0467 (12) | 0.0404 (12) | −0.0056 (10) | 0.0051 (9) | −0.0001 (10) |
N3 | 0.0537 (14) | 0.0690 (16) | 0.0425 (13) | −0.0065 (12) | 0.0096 (10) | 0.0018 (11) |
N4 | 0.0543 (14) | 0.0501 (13) | 0.0403 (12) | −0.0022 (11) | −0.0003 (10) | −0.0053 (10) |
S1 | 0.0651 (6) | 0.1034 (8) | 0.0730 (6) | −0.0009 (5) | 0.0056 (4) | 0.0362 (5) |
C1—C2 | 1.349 (4) | C9—S1 | 1.725 (3) |
C1—S1 | 1.700 (4) | C10—C11 | 1.497 (4) |
C1—H1 | 0.9300 | C10—H10A | 0.9700 |
C2—N4 | 1.386 (3) | C10—H10B | 0.9700 |
C2—C3 | 1.471 (4) | C11—N3 | 1.307 (3) |
C3—C8 | 1.381 (4) | C11—N2 | 1.351 (3) |
C3—C4 | 1.390 (4) | C12—C13 | 1.382 (4) |
C4—C5 | 1.370 (5) | C12—C16 | 1.389 (4) |
C4—H4 | 0.9300 | C12—N3 | 1.392 (3) |
C5—C6 | 1.360 (6) | C13—C14 | 1.385 (4) |
C5—H5 | 0.9300 | C13—H13 | 0.9300 |
C6—C7 | 1.375 (5) | C14—C15 | 1.379 (4) |
C6—H6 | 0.9300 | C14—H14 | 0.9300 |
C7—C8 | 1.392 (5) | C15—N1 | 1.338 (4) |
C7—H7 | 0.9300 | C15—H15 | 0.9300 |
C8—H8 | 0.9300 | C16—N1 | 1.333 (3) |
C9—N4 | 1.298 (3) | C16—N2 | 1.370 (3) |
C9—C10 | 1.497 (4) | N2—H2A | 0.8600 |
C2—C1—S1 | 111.4 (2) | C9—C10—H10A | 109.6 |
C2—C1—H1 | 124.3 | C11—C10—H10B | 109.6 |
S1—C1—H1 | 124.3 | C9—C10—H10B | 109.6 |
C1—C2—N4 | 114.0 (3) | H10A—C10—H10B | 108.1 |
C1—C2—C3 | 126.2 (3) | N3—C11—N2 | 114.2 (2) |
N4—C2—C3 | 119.7 (3) | N3—C11—C10 | 125.2 (2) |
C8—C3—C4 | 117.9 (3) | N2—C11—C10 | 120.5 (2) |
C8—C3—C2 | 121.3 (3) | C13—C12—C16 | 117.4 (2) |
C4—C3—C2 | 120.7 (3) | C13—C12—N3 | 132.8 (3) |
C5—C4—C3 | 121.2 (4) | C16—C12—N3 | 109.9 (2) |
C5—C4—H4 | 119.4 | C12—C13—C14 | 116.8 (3) |
C3—C4—H4 | 119.4 | C12—C13—H13 | 121.6 |
C6—C5—C4 | 120.7 (4) | C14—C13—H13 | 121.6 |
C6—C5—H5 | 119.6 | C15—C14—C13 | 120.8 (3) |
C4—C5—H5 | 119.6 | C15—C14—H14 | 119.6 |
C5—C6—C7 | 119.5 (4) | C13—C14—H14 | 119.6 |
C5—C6—H6 | 120.3 | N1—C15—C14 | 124.2 (3) |
C7—C6—H6 | 120.3 | N1—C15—H15 | 117.9 |
C6—C7—C8 | 120.4 (4) | C14—C15—H15 | 117.9 |
C6—C7—H7 | 119.8 | N1—C16—N2 | 126.9 (2) |
C8—C7—H7 | 119.8 | N1—C16—C12 | 127.5 (2) |
C3—C8—C7 | 120.3 (3) | N2—C16—C12 | 105.6 (2) |
C3—C8—H8 | 119.8 | C16—N1—C15 | 113.4 (2) |
C7—C8—H8 | 119.8 | C11—N2—C16 | 106.4 (2) |
N4—C9—C10 | 124.4 (3) | C11—N2—H2A | 126.8 |
N4—C9—S1 | 114.4 (2) | C16—N2—H2A | 126.8 |
C10—C9—S1 | 120.9 (2) | C11—N3—C12 | 103.9 (2) |
C11—C10—C9 | 110.3 (2) | C9—N4—C2 | 111.1 (2) |
C11—C10—H10A | 109.6 | C1—S1—C9 | 89.08 (15) |
S1—C1—C2—N4 | −0.4 (4) | C13—C12—C16—N1 | −0.2 (4) |
S1—C1—C2—C3 | 179.2 (2) | N3—C12—C16—N1 | −179.6 (2) |
C1—C2—C3—C8 | 171.0 (3) | C13—C12—C16—N2 | 179.5 (2) |
N4—C2—C3—C8 | −9.5 (4) | N3—C12—C16—N2 | 0.1 (3) |
C1—C2—C3—C4 | −8.9 (4) | N2—C16—N1—C15 | 179.8 (3) |
N4—C2—C3—C4 | 170.7 (3) | C12—C16—N1—C15 | −0.6 (4) |
C8—C3—C4—C5 | 0.5 (5) | C14—C15—N1—C16 | 0.9 (4) |
C2—C3—C4—C5 | −179.6 (3) | N3—C11—N2—C16 | −0.6 (3) |
C3—C4—C5—C6 | 0.2 (6) | C10—C11—N2—C16 | −178.0 (2) |
C4—C5—C6—C7 | −0.8 (6) | N1—C16—N2—C11 | 180.0 (2) |
C5—C6—C7—C8 | 0.8 (6) | C12—C16—N2—C11 | 0.3 (3) |
C4—C3—C8—C7 | −0.6 (4) | N2—C11—N3—C12 | 0.6 (3) |
C2—C3—C8—C7 | 179.6 (3) | C10—C11—N3—C12 | 177.9 (2) |
C6—C7—C8—C3 | −0.1 (5) | C13—C12—N3—C11 | −179.7 (3) |
N4—C9—C10—C11 | −82.2 (3) | C16—C12—N3—C11 | −0.4 (3) |
S1—C9—C10—C11 | 91.6 (3) | C10—C9—N4—C2 | 174.2 (2) |
C9—C10—C11—N3 | −93.2 (3) | S1—C9—N4—C2 | 0.0 (3) |
C9—C10—C11—N2 | 83.9 (3) | C1—C2—N4—C9 | 0.2 (3) |
C16—C12—C13—C14 | 0.6 (4) | C3—C2—N4—C9 | −179.4 (2) |
N3—C12—C13—C14 | 179.9 (3) | C2—C1—S1—C9 | 0.3 (3) |
C12—C13—C14—C15 | −0.3 (5) | N4—C9—S1—C1 | −0.2 (2) |
C13—C14—C15—N1 | −0.5 (5) | C10—C9—S1—C1 | −174.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.86 | 2.01 | 2.863 (3) | 170 |
C8—H8···N4 | 0.93 | 2.57 | 2.884 (4) | 100 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H12N4S |
Mr | 292.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.685 (6), 5.277 (2), 21.389 (9) |
β (°) | 100.577 (6) |
V (Å3) | 1407.5 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.35 × 0.21 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.925, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6901, 2509, 2210 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.598 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.146, 1.18 |
No. of reflections | 2509 |
No. of parameters | 190 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.23 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
C1—C2 | 1.349 (4) | C11—N2 | 1.351 (3) |
C1—S1 | 1.700 (4) | C12—N3 | 1.392 (3) |
C9—N4 | 1.298 (3) | C15—N1 | 1.338 (4) |
C9—S1 | 1.725 (3) | C16—N1 | 1.333 (3) |
C11—N3 | 1.307 (3) | C16—N2 | 1.370 (3) |
C11—C10—C9 | 110.3 (2) | C1—S1—C9 | 89.08 (15) |
C9—N4—C2 | 111.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.86 | 2.01 | 2.863 (3) | 170 |
C8—H8···N4 | 0.93 | 2.57 | 2.884 (4) | 100 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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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).