Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040146/ob6593sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040146/ob6593Isup2.hkl |
CCDC reference: 296619
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.104
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. CL1 .. 2.87 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
α-Bromo-α-(1H-1,2,4-triazol-1-yl)-4-chloroacetophenone (2.66 g, 10 mmol) and dry sodium thiocyanate (0.97 g, 12 mmol) were stirred in ethanol (25 ml) for 3 h at 323 K. A solution of aniline (0.93 g, 10 mmol) in ethanol (5 ml) was added in one portion and the reaction mixture was stirred for 8 h. The ethanol was distilled off, and ethyl acetate and water were added (Volumes?). The aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were dried with MgSO4, and the solvent was removed in vacuo. The residue was then purified via column chromatography on silica gel (Eluent?) to afford (I) in a yield of 15% (m.p. 483 K). Analysis: C 57.56, H 3.52, N 20.03%; calculated for [Formula missing]: C 57.71, H 3.42, N 19.79%. Spectroscopic analysis: 1H NMR (DMSO, δ, p.p.m.): 10.629 (s, 1H, N—H), 8.858 (s, 1H, Tr—H), 8.369 (s, 1H, Tr—H), 7.717, 7.691 (d, 2H, p-Cl—Ph—H, J = 7.8 Hz), 7.462, 7.436 (d, 2H, p-Cl—Ph—H, J = 7.8 Hz), 7.411–7.023 (m, 5H, Ph—H).
The amino H atom was located in a difference Fourier map and refined isotropically, with the distance restraint N—H = 0.83 (3) Å. Other H atoms were placed in calculated positions, with C—H = 0.93 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).
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.
C17H12ClN5S | F(000) = 728 |
Mr = 353.83 | Dx = 1.469 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yn | Cell parameters from 3277 reflections |
a = 9.5139 (18) Å | θ = 2.2–26.4° |
b = 13.681 (3) Å | µ = 0.38 mm−1 |
c = 12.439 (3) Å | T = 294 K |
β = 98.828 (3)° | Parallelepiped, colourless |
V = 1599.9 (5) Å3 | 0.24 × 0.22 × 0.20 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3279 independent reflections |
Radiation source: fine-focus sealed tube | 2449 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ϕ and ω scans | θmax = 26.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→11 |
Tmin = 0.903, Tmax = 0.928 | k = −11→17 |
8842 measured reflections | l = −15→15 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0499P)2 + 0.5099P] where P = (Fo2 + 2Fc2)/3 |
3279 reflections | (Δ/σ)max < 0.001 |
221 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C17H12ClN5S | V = 1599.9 (5) Å3 |
Mr = 353.83 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.5139 (18) Å | µ = 0.38 mm−1 |
b = 13.681 (3) Å | T = 294 K |
c = 12.439 (3) Å | 0.24 × 0.22 × 0.20 mm |
β = 98.828 (3)° |
Bruker SMART CCD area-detector diffractometer | 3279 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2449 reflections with I > 2σ(I) |
Tmin = 0.903, Tmax = 0.928 | Rint = 0.031 |
8842 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.23 e Å−3 |
3279 reflections | Δρmin = −0.33 e Å−3 |
221 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 | ||
S1 | 0.62799 (5) | 0.29951 (4) | 0.77969 (5) | 0.04107 (16) | |
Cl1 | 0.37789 (8) | 0.87301 (4) | 0.94633 (6) | 0.0688 (2) | |
N1 | 0.94670 (18) | 0.55483 (14) | 0.74501 (17) | 0.0498 (5) | |
N2 | 0.86744 (17) | 0.48455 (14) | 0.88833 (15) | 0.0474 (5) | |
N3 | 0.77183 (15) | 0.47228 (12) | 0.79540 (13) | 0.0340 (4) | |
N4 | 0.41660 (16) | 0.39374 (11) | 0.83975 (13) | 0.0341 (4) | |
N5 | 0.38380 (17) | 0.22234 (13) | 0.82124 (15) | 0.0400 (4) | |
H5 | 0.427 (3) | 0.1713 (19) | 0.809 (2) | 0.054 (7)* | |
C1 | 0.9687 (2) | 0.53416 (17) | 0.8525 (2) | 0.0497 (6) | |
H1 | 1.0505 | 0.5538 | 0.8982 | 0.060* | |
C2 | 0.8222 (2) | 0.51438 (17) | 0.71211 (18) | 0.0455 (5) | |
H2 | 0.7756 | 0.5150 | 0.6407 | 0.055* | |
C3 | 0.64023 (19) | 0.42529 (14) | 0.79944 (16) | 0.0340 (4) | |
C4 | 0.52166 (18) | 0.46324 (14) | 0.83231 (15) | 0.0314 (4) | |
C5 | 0.49206 (18) | 0.56457 (14) | 0.86172 (15) | 0.0321 (4) | |
C6 | 0.5810 (2) | 0.64335 (15) | 0.8485 (2) | 0.0469 (5) | |
H6 | 0.6656 | 0.6323 | 0.8215 | 0.056* | |
C7 | 0.5462 (2) | 0.73707 (16) | 0.8746 (2) | 0.0500 (6) | |
H7 | 0.6065 | 0.7888 | 0.8650 | 0.060* | |
C8 | 0.4216 (2) | 0.75392 (15) | 0.91490 (17) | 0.0414 (5) | |
C9 | 0.3323 (2) | 0.67798 (16) | 0.93032 (18) | 0.0433 (5) | |
H9 | 0.2484 | 0.6897 | 0.9580 | 0.052* | |
C10 | 0.3683 (2) | 0.58415 (15) | 0.90442 (17) | 0.0382 (5) | |
H10 | 0.3083 | 0.5327 | 0.9158 | 0.046* | |
C11 | 0.45743 (18) | 0.30659 (14) | 0.81708 (16) | 0.0341 (4) | |
C12 | 0.25823 (18) | 0.20682 (14) | 0.86579 (16) | 0.0336 (4) | |
C13 | 0.2227 (2) | 0.11027 (15) | 0.88219 (18) | 0.0418 (5) | |
H13 | 0.2802 | 0.0602 | 0.8630 | 0.050* | |
C14 | 0.1027 (2) | 0.08796 (17) | 0.9267 (2) | 0.0524 (6) | |
H14 | 0.0800 | 0.0230 | 0.9379 | 0.063* | |
C15 | 0.0162 (2) | 0.16115 (18) | 0.9548 (2) | 0.0563 (6) | |
H15 | −0.0646 | 0.1461 | 0.9852 | 0.068* | |
C16 | 0.0503 (2) | 0.25682 (18) | 0.9374 (2) | 0.0567 (6) | |
H16 | −0.0083 | 0.3064 | 0.9560 | 0.068* | |
C17 | 0.1707 (2) | 0.28099 (15) | 0.8926 (2) | 0.0474 (6) | |
H17 | 0.1922 | 0.3460 | 0.8807 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0321 (3) | 0.0355 (3) | 0.0606 (4) | −0.0025 (2) | 0.0230 (2) | −0.0066 (2) |
Cl1 | 0.0836 (5) | 0.0350 (3) | 0.0948 (5) | 0.0131 (3) | 0.0356 (4) | −0.0012 (3) |
N1 | 0.0381 (10) | 0.0477 (11) | 0.0685 (13) | −0.0086 (8) | 0.0236 (9) | 0.0072 (9) |
N2 | 0.0342 (9) | 0.0550 (12) | 0.0529 (11) | −0.0074 (8) | 0.0064 (8) | 0.0106 (9) |
N3 | 0.0261 (8) | 0.0353 (9) | 0.0431 (9) | −0.0013 (7) | 0.0131 (7) | 0.0029 (7) |
N4 | 0.0259 (8) | 0.0307 (8) | 0.0474 (10) | −0.0025 (6) | 0.0115 (7) | −0.0021 (7) |
N5 | 0.0300 (9) | 0.0293 (9) | 0.0648 (12) | −0.0029 (7) | 0.0202 (8) | −0.0093 (8) |
C1 | 0.0289 (10) | 0.0508 (13) | 0.0696 (16) | −0.0066 (9) | 0.0081 (10) | 0.0065 (12) |
C2 | 0.0412 (11) | 0.0535 (13) | 0.0451 (12) | −0.0067 (10) | 0.0169 (9) | 0.0073 (10) |
C3 | 0.0294 (10) | 0.0315 (10) | 0.0438 (11) | −0.0033 (8) | 0.0139 (8) | 0.0010 (8) |
C4 | 0.0258 (9) | 0.0336 (10) | 0.0359 (10) | −0.0028 (8) | 0.0082 (8) | 0.0024 (8) |
C5 | 0.0276 (9) | 0.0333 (10) | 0.0359 (10) | −0.0009 (8) | 0.0063 (8) | 0.0029 (8) |
C6 | 0.0391 (11) | 0.0376 (11) | 0.0699 (15) | −0.0035 (9) | 0.0278 (11) | −0.0001 (11) |
C7 | 0.0495 (13) | 0.0314 (11) | 0.0742 (16) | −0.0051 (10) | 0.0256 (11) | 0.0006 (11) |
C8 | 0.0484 (12) | 0.0315 (10) | 0.0460 (12) | 0.0065 (9) | 0.0121 (10) | −0.0003 (9) |
C9 | 0.0354 (11) | 0.0448 (12) | 0.0523 (13) | 0.0055 (9) | 0.0153 (9) | −0.0001 (10) |
C10 | 0.0312 (10) | 0.0363 (11) | 0.0486 (12) | −0.0039 (8) | 0.0113 (9) | −0.0010 (9) |
C11 | 0.0261 (9) | 0.0356 (11) | 0.0423 (11) | −0.0028 (8) | 0.0112 (8) | −0.0037 (9) |
C12 | 0.0272 (9) | 0.0337 (10) | 0.0411 (11) | −0.0021 (8) | 0.0093 (8) | −0.0040 (8) |
C13 | 0.0400 (11) | 0.0327 (11) | 0.0550 (13) | 0.0015 (9) | 0.0144 (10) | 0.0012 (9) |
C14 | 0.0536 (13) | 0.0399 (12) | 0.0689 (16) | −0.0076 (10) | 0.0258 (12) | 0.0090 (11) |
C15 | 0.0469 (13) | 0.0556 (15) | 0.0745 (17) | −0.0091 (11) | 0.0351 (12) | −0.0005 (12) |
C16 | 0.0426 (12) | 0.0475 (13) | 0.0882 (18) | −0.0004 (10) | 0.0356 (12) | −0.0097 (13) |
C17 | 0.0378 (11) | 0.0319 (11) | 0.0774 (16) | −0.0034 (9) | 0.0242 (11) | −0.0049 (10) |
S1—C3 | 1.740 (2) | C6—C7 | 1.376 (3) |
S1—C11 | 1.7579 (18) | C6—H6 | 0.9300 |
Cl1—C8 | 1.741 (2) | C7—C8 | 1.376 (3) |
N1—C2 | 1.314 (3) | C7—H7 | 0.9300 |
N1—C1 | 1.351 (3) | C8—C9 | 1.374 (3) |
N2—C1 | 1.311 (3) | C9—C10 | 1.380 (3) |
N2—N3 | 1.367 (2) | C9—H9 | 0.9300 |
N3—C2 | 1.337 (2) | C10—H10 | 0.9300 |
N3—C3 | 1.415 (2) | C12—C17 | 1.385 (3) |
N4—C11 | 1.298 (2) | C12—C13 | 1.386 (3) |
N4—C4 | 1.393 (2) | C13—C14 | 1.378 (3) |
N5—C11 | 1.354 (2) | C13—H13 | 0.9300 |
N5—C12 | 1.408 (2) | C14—C15 | 1.375 (3) |
N5—H5 | 0.83 (3) | C14—H14 | 0.9300 |
C1—H1 | 0.9300 | C15—C16 | 1.374 (3) |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
C3—C4 | 1.360 (3) | C16—C17 | 1.388 (3) |
C4—C5 | 1.472 (3) | C16—H16 | 0.9300 |
C5—C10 | 1.390 (3) | C17—H17 | 0.9300 |
C5—C6 | 1.396 (3) | ||
C3—S1—C11 | 87.29 (9) | C9—C8—C7 | 120.66 (19) |
C2—N1—C1 | 102.45 (17) | C9—C8—Cl1 | 120.17 (16) |
C1—N2—N3 | 101.80 (17) | C7—C8—Cl1 | 119.18 (16) |
C2—N3—N2 | 109.34 (16) | C8—C9—C10 | 119.35 (18) |
C2—N3—C3 | 130.37 (18) | C8—C9—H9 | 120.3 |
N2—N3—C3 | 120.21 (15) | C10—C9—H9 | 120.3 |
C11—N4—C4 | 111.76 (15) | C9—C10—C5 | 121.59 (19) |
C11—N5—C12 | 128.22 (17) | C9—C10—H10 | 119.2 |
C11—N5—H5 | 115.7 (17) | C5—C10—H10 | 119.2 |
C12—N5—H5 | 114.5 (17) | N4—C11—N5 | 126.85 (17) |
N2—C1—N1 | 115.7 (2) | N4—C11—S1 | 115.28 (14) |
N2—C1—H1 | 122.1 | N5—C11—S1 | 117.86 (14) |
N1—C1—H1 | 122.1 | C17—C12—C13 | 119.55 (17) |
N1—C2—N3 | 110.7 (2) | C17—C12—N5 | 124.18 (18) |
N1—C2—H2 | 124.7 | C13—C12—N5 | 116.27 (17) |
N3—C2—H2 | 124.7 | C14—C13—C12 | 120.42 (19) |
C4—C3—N3 | 128.04 (18) | C14—C13—H13 | 119.8 |
C4—C3—S1 | 112.29 (13) | C12—C13—H13 | 119.8 |
N3—C3—S1 | 119.00 (13) | C15—C14—C13 | 120.4 (2) |
C3—C4—N4 | 113.33 (17) | C15—C14—H14 | 119.8 |
C3—C4—C5 | 129.29 (17) | C13—C14—H14 | 119.8 |
N4—C4—C5 | 117.37 (15) | C16—C15—C14 | 119.2 (2) |
C10—C5—C6 | 117.45 (18) | C16—C15—H15 | 120.4 |
C10—C5—C4 | 118.81 (16) | C14—C15—H15 | 120.4 |
C6—C5—C4 | 123.73 (17) | C15—C16—C17 | 121.3 (2) |
C7—C6—C5 | 121.27 (19) | C15—C16—H16 | 119.3 |
C7—C6—H6 | 119.4 | C17—C16—H16 | 119.3 |
C5—C6—H6 | 119.4 | C12—C17—C16 | 119.0 (2) |
C8—C7—C6 | 119.7 (2) | C12—C17—H17 | 120.5 |
C8—C7—H7 | 120.2 | C16—C17—H17 | 120.5 |
C6—C7—H7 | 120.2 | ||
C1—N2—N3—C2 | 0.2 (2) | C5—C6—C7—C8 | 0.2 (4) |
C1—N2—N3—C3 | −176.79 (18) | C6—C7—C8—C9 | 0.6 (4) |
N3—N2—C1—N1 | 0.0 (3) | C6—C7—C8—Cl1 | −179.37 (19) |
C2—N1—C1—N2 | −0.3 (3) | C7—C8—C9—C10 | −0.3 (3) |
C1—N1—C2—N3 | 0.4 (2) | Cl1—C8—C9—C10 | 179.66 (16) |
N2—N3—C2—N1 | −0.4 (2) | C8—C9—C10—C5 | −0.8 (3) |
C3—N3—C2—N1 | 176.20 (19) | C6—C5—C10—C9 | 1.6 (3) |
C2—N3—C3—C4 | −97.8 (3) | C4—C5—C10—C9 | −177.90 (19) |
N2—N3—C3—C4 | 78.5 (3) | C4—N4—C11—N5 | 176.91 (19) |
C2—N3—C3—S1 | 92.3 (2) | C4—N4—C11—S1 | −1.9 (2) |
N2—N3—C3—S1 | −91.4 (2) | C12—N5—C11—N4 | −10.5 (4) |
C11—S1—C3—C4 | 0.52 (16) | C12—N5—C11—S1 | 168.27 (17) |
C11—S1—C3—N3 | 171.89 (16) | C3—S1—C11—N4 | 0.80 (16) |
N3—C3—C4—N4 | −172.05 (18) | C3—S1—C11—N5 | −178.09 (17) |
S1—C3—C4—N4 | −1.7 (2) | C11—N5—C12—C17 | 14.8 (3) |
N3—C3—C4—C5 | 6.9 (3) | C11—N5—C12—C13 | −165.6 (2) |
S1—C3—C4—C5 | 177.28 (16) | C17—C12—C13—C14 | −1.2 (3) |
C11—N4—C4—C3 | 2.3 (2) | N5—C12—C13—C14 | 179.2 (2) |
C11—N4—C4—C5 | −176.81 (17) | C12—C13—C14—C15 | 0.4 (4) |
C3—C4—C5—C10 | −173.1 (2) | C13—C14—C15—C16 | 0.3 (4) |
N4—C4—C5—C10 | 5.8 (3) | C14—C15—C16—C17 | −0.3 (4) |
C3—C4—C5—C6 | 7.4 (3) | C13—C12—C17—C16 | 1.3 (3) |
N4—C4—C5—C6 | −173.69 (19) | N5—C12—C17—C16 | −179.2 (2) |
C10—C5—C6—C7 | −1.3 (3) | C15—C16—C17—C12 | −0.5 (4) |
C4—C5—C6—C7 | 178.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···N1i | 0.83 (3) | 2.17 (3) | 2.990 (2) | 170 (2) |
C13—H13···Cl1ii | 0.93 | 2.87 | 3.605 (2) | 137 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C17H12ClN5S |
Mr | 353.83 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 9.5139 (18), 13.681 (3), 12.439 (3) |
β (°) | 98.828 (3) |
V (Å3) | 1599.9 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.38 |
Crystal size (mm) | 0.24 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.903, 0.928 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8842, 3279, 2449 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.104, 1.02 |
No. of reflections | 3279 |
No. of parameters | 221 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.33 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
S1—C3 | 1.740 (2) | N3—C3 | 1.415 (2) |
S1—C11 | 1.7579 (18) | N4—C11 | 1.298 (2) |
N1—C2 | 1.314 (3) | N4—C4 | 1.393 (2) |
N1—C1 | 1.351 (3) | N5—C11 | 1.354 (2) |
N2—N3 | 1.367 (2) | N5—C12 | 1.408 (2) |
N3—C2 | 1.337 (2) | ||
C3—S1—C11 | 87.29 (9) | C11—N5—C12 | 128.22 (17) |
C2—N1—C1 | 102.45 (17) | N2—C1—N1 | 115.7 (2) |
C1—N2—N3 | 101.80 (17) | N1—C2—N3 | 110.7 (2) |
C2—N3—N2 | 109.34 (16) | C4—C3—S1 | 112.29 (13) |
C2—N3—C3 | 130.37 (18) | C3—C4—N4 | 113.33 (17) |
C11—N4—C4 | 111.76 (15) | ||
N2—N3—C3—C4 | 78.5 (3) | C12—N5—C11—N4 | −10.5 (4) |
C3—C4—C5—C10 | −173.1 (2) | C11—N5—C12—C17 | 14.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···N1i | 0.83 (3) | 2.17 (3) | 2.990 (2) | 170 (2) |
C13—H13···Cl1ii | 0.93 | 2.87 | 3.605 (2) | 137 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x, y−1, z. |
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The aminothiazole ring system has found application in drug development for the treatment of allergies, hypertension, inflammation, schizophrenia, and bacterial and HIV infections (Arcadi et al., 1999). For example, aminothiazole BMS-387032 {N-[5-({[5-(1,1-dimethylethyl)-2-oxazolyl]methyl}thio)-2-thizolyl]-4- piperidinecarboxamide} has been selected to enter clinical development as an antitumour agent (Misra et al., 2004). In the search for novel aminothiazole compounds with potent antitumour activities and as a continuation of our studies of thiazole molecules (Shao et al., 2005), we have designed and synthesized such 2-aminothiazole compounds incorporating the 1H-1,2,4-triazole unit. In this paper, we report the crystal structure of the title compound, (I).
Fig. 1 shows the molecular structure of (I), which contains four planar subunits, namely the thiazole ring (P1), the substituted C5–C10 benzene ring (P2), the C12–C17 phenyl ring (P3) and the triazole ring (P4). The dihedral angles between P1 and P2, P3 and P4 are 6.1 (4), 14.0 (3) and 85.9 (2)°, respectively. The C11—N5 and C3—N3 bond lengths in (I) [1.354 (2) and 1.415 (2) Å] are longer than the corresponding distances in 2-amino-4-(2,5-dichlorophenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazole [1.339 (3) and 1.402 (3) Å; Shao et al., 2004].
In (I), the molecules are associated via N—H···N and C—H···Cl interactions (Table 2 and Fig. 2).