organic compounds
The title imidazole, C17H13ClN2OS, was obtained by unusual rearrangement of the pyrimidinium salt. The structure was characterized by 1H NMR spectroscopy and X-ray diffraction. A mechanism of transformation (pyrimidinium salt → title imidazole) is proposed.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004120/at6084sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004120/at60841sup2.hkl |
CCDC reference: 601103
Computing details top
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; 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, 1997) and PLUTON97 (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
4-Benzoyl-5-(4-chlorophenyl)-2-(methylsulfanyl)-1H-imidazole top
Crystal data top
C17H13ClN2OS | F(000) = 680 |
Mr = 328.81 | Dx = 1.388 Mg m−3 |
Monoclinic, P21/c | Melting point: 468 K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.5418 Å |
a = 7.2814 (15) Å | Cell parameters from 25 reflections |
b = 23.650 (3) Å | θ = 32–35° |
c = 9.752 (5) Å | µ = 3.41 mm−1 |
β = 110.46 (3)° | T = 293 K |
V = 1573.4 (9) Å3 | Prism, colourless |
Z = 4 | 0.1 × 0.1 × 0.1 mm |
Data collection top
Enraf–Nonius CAD4 diffractometer | Rint = 0.056 |
Radiation source: Enraf–Nonius FR590 | θmax = 74.9°, θmin = 3.7° |
Graphite monochromator | h = −9→8 |
Non–profiled ω scans | k = 0→29 |
3236 measured reflections | l = 0→12 |
3236 independent reflections | 1 standard reflections every 120 min |
1639 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement top
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.86 | w = 1/[σ2(Fo2) + (0.0051P)2] where P = (Fo2 + 2Fc2)/3 |
3236 reflections | (Δ/σ)max = 0.001 |
204 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.14922 (14) | 0.69610 (4) | 0.62147 (9) | 0.0644 (3) | |
Cl1 | 1.06895 (13) | 0.93313 (4) | 0.41461 (8) | 0.0783 (3) | |
O1 | 0.5764 (3) | 0.84701 (8) | 1.03731 (18) | 0.0608 (6) | |
N1 | 0.4198 (4) | 0.76941 (10) | 0.5930 (3) | 0.0399 (6) | |
H1 | 0.396 (4) | 0.7530 (12) | 0.509 (3) | 0.085 (12)* | |
C2 | 0.3181 (4) | 0.75069 (11) | 0.6784 (3) | 0.0417 (7) | |
N3 | 0.3643 (3) | 0.77929 (9) | 0.8026 (2) | 0.0392 (6) | |
C4 | 0.4973 (4) | 0.82006 (11) | 0.7940 (3) | 0.0353 (7) | |
C5 | 0.5366 (4) | 0.81356 (11) | 0.6666 (3) | 0.0382 (7) | |
C6 | 0.5650 (4) | 0.86158 (12) | 0.9144 (3) | 0.0413 (7) | |
C7 | 0.6097 (4) | 0.92065 (11) | 0.8860 (3) | 0.0386 (7) | |
C8 | 0.5232 (4) | 0.94639 (12) | 0.7513 (3) | 0.0460 (8) | |
H8 | 0.4413 | 0.9254 | 0.6730 | 0.055* | |
C9 | 0.5566 (5) | 1.00231 (13) | 0.7315 (4) | 0.0616 (10) | |
H9 | 0.4980 | 1.0189 | 0.6400 | 0.074* | |
C10 | 0.6754 (5) | 1.03391 (13) | 0.8450 (4) | 0.0713 (11) | |
H10 | 0.6981 | 1.0718 | 0.8307 | 0.086* | |
C11 | 0.7613 (5) | 1.00965 (14) | 0.9807 (4) | 0.0661 (10) | |
H11 | 0.8416 | 1.0313 | 1.0581 | 0.079* | |
C12 | 0.7289 (4) | 0.95296 (13) | 1.0030 (3) | 0.0566 (9) | |
H12 | 0.7863 | 0.9368 | 1.0950 | 0.068* | |
C13 | 0.6707 (4) | 0.84184 (11) | 0.6065 (3) | 0.0368 (7) | |
C14 | 0.6148 (4) | 0.85090 (11) | 0.4555 (3) | 0.0439 (8) | |
H14 | 0.4930 | 0.8383 | 0.3937 | 0.053* | |
C15 | 0.7378 (4) | 0.87818 (12) | 0.3971 (3) | 0.0484 (8) | |
H15 | 0.7003 | 0.8836 | 0.2965 | 0.058* | |
C16 | 0.9154 (4) | 0.89715 (13) | 0.4886 (3) | 0.0495 (8) | |
C17 | 0.9765 (4) | 0.88870 (12) | 0.6380 (3) | 0.0529 (9) | |
H17 | 1.0983 | 0.9017 | 0.6988 | 0.064* | |
C18 | 0.8542 (4) | 0.86087 (12) | 0.6948 (3) | 0.0440 (7) | |
H18 | 0.8953 | 0.8546 | 0.7952 | 0.053* | |
C19 | 0.0096 (5) | 0.70910 (13) | 0.7355 (3) | 0.0882 (12) | |
H19A | −0.0133 | 0.7490 | 0.7385 | 0.132* | |
H19B | 0.0803 | 0.6957 | 0.8326 | 0.132* | |
H19C | −0.1136 | 0.6897 | 0.6969 | 0.132* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0885 (7) | 0.0512 (5) | 0.0530 (5) | −0.0279 (5) | 0.0241 (5) | −0.0105 (5) |
Cl1 | 0.0735 (6) | 0.1121 (8) | 0.0561 (5) | −0.0308 (6) | 0.0314 (5) | 0.0028 (6) |
O1 | 0.0996 (18) | 0.0555 (14) | 0.0259 (11) | −0.0144 (13) | 0.0203 (11) | 0.0011 (10) |
N1 | 0.0569 (17) | 0.0325 (14) | 0.0342 (14) | −0.0024 (13) | 0.0207 (13) | −0.0015 (12) |
C2 | 0.060 (2) | 0.0304 (16) | 0.0359 (17) | 0.0023 (15) | 0.0189 (15) | 0.0013 (13) |
N3 | 0.0569 (16) | 0.0345 (14) | 0.0293 (12) | −0.0070 (12) | 0.0190 (11) | −0.0006 (11) |
C4 | 0.0455 (18) | 0.0314 (16) | 0.0296 (15) | −0.0057 (13) | 0.0137 (13) | −0.0020 (12) |
C5 | 0.0470 (19) | 0.0335 (17) | 0.0364 (16) | −0.0011 (14) | 0.0174 (14) | −0.0003 (13) |
C6 | 0.0474 (19) | 0.0441 (19) | 0.0351 (16) | −0.0033 (16) | 0.0178 (14) | −0.0053 (15) |
C7 | 0.0446 (18) | 0.0379 (18) | 0.0359 (16) | −0.0071 (14) | 0.0175 (13) | −0.0129 (14) |
C8 | 0.056 (2) | 0.0369 (17) | 0.0493 (18) | 0.0046 (15) | 0.0238 (15) | −0.0022 (15) |
C9 | 0.087 (3) | 0.040 (2) | 0.069 (2) | 0.002 (2) | 0.041 (2) | 0.0043 (18) |
C10 | 0.095 (3) | 0.035 (2) | 0.100 (3) | −0.014 (2) | 0.053 (3) | −0.004 (2) |
C11 | 0.076 (3) | 0.056 (2) | 0.071 (3) | −0.026 (2) | 0.031 (2) | −0.028 (2) |
C12 | 0.061 (2) | 0.056 (2) | 0.053 (2) | −0.0161 (18) | 0.0199 (17) | −0.0101 (18) |
C13 | 0.0471 (18) | 0.0361 (16) | 0.0327 (15) | 0.0025 (15) | 0.0208 (13) | −0.0002 (14) |
C14 | 0.0495 (19) | 0.051 (2) | 0.0299 (15) | −0.0069 (16) | 0.0124 (13) | −0.0031 (14) |
C15 | 0.059 (2) | 0.057 (2) | 0.0335 (17) | −0.0020 (17) | 0.0221 (15) | 0.0007 (15) |
C16 | 0.046 (2) | 0.067 (2) | 0.0397 (17) | −0.0029 (17) | 0.0203 (15) | 0.0010 (17) |
C17 | 0.046 (2) | 0.069 (2) | 0.0448 (18) | −0.0056 (18) | 0.0168 (15) | −0.0039 (17) |
C18 | 0.0444 (18) | 0.056 (2) | 0.0309 (15) | 0.0027 (16) | 0.0114 (13) | 0.0031 (15) |
C19 | 0.080 (3) | 0.076 (3) | 0.120 (3) | −0.032 (2) | 0.050 (2) | −0.024 (3) |
Geometric parameters (Å, º) top
S1—C2 | 1.735 (3) | C10—C11 | 1.375 (4) |
S1—C19 | 1.776 (3) | C10—H10 | 0.9300 |
Cl1—C16 | 1.749 (3) | C11—C12 | 1.391 (4) |
O1—C6 | 1.221 (3) | C11—H11 | 0.9300 |
N1—C2 | 1.367 (3) | C12—H12 | 0.9300 |
N1—C5 | 1.379 (3) | C13—C18 | 1.387 (3) |
N1—H1 | 0.86 (3) | C13—C14 | 1.400 (3) |
C2—N3 | 1.324 (3) | C14—C15 | 1.378 (3) |
N3—C4 | 1.390 (3) | C14—H14 | 0.9300 |
C4—C5 | 1.378 (3) | C15—C16 | 1.365 (3) |
C4—C6 | 1.477 (3) | C15—H15 | 0.9300 |
C5—C13 | 1.465 (3) | C16—C17 | 1.381 (3) |
C6—C7 | 1.482 (3) | C17—C18 | 1.370 (3) |
C7—C8 | 1.384 (3) | C17—H17 | 0.9300 |
C7—C12 | 1.395 (3) | C18—H18 | 0.9300 |
C8—C9 | 1.371 (3) | C19—H19A | 0.9600 |
C8—H8 | 0.9300 | C19—H19B | 0.9600 |
C9—C10 | 1.365 (4) | C19—H19C | 0.9600 |
C9—H9 | 0.9300 | ||
C2—S1—C19 | 99.66 (14) | C10—C11—H11 | 119.8 |
C2—N1—C5 | 107.2 (2) | C12—C11—H11 | 119.8 |
C2—N1—H1 | 117 (2) | C11—C12—C7 | 119.4 (3) |
C5—N1—H1 | 136 (2) | C11—C12—H12 | 120.3 |
N3—C2—N1 | 111.9 (3) | C7—C12—H12 | 120.3 |
N3—C2—S1 | 126.7 (2) | C18—C13—C14 | 117.8 (3) |
N1—C2—S1 | 121.4 (2) | C18—C13—C5 | 122.1 (2) |
C2—N3—C4 | 105.0 (2) | C14—C13—C5 | 120.1 (3) |
C5—C4—N3 | 110.2 (2) | C15—C14—C13 | 121.0 (3) |
C5—C4—C6 | 132.4 (3) | C15—C14—H14 | 119.5 |
N3—C4—C6 | 117.4 (2) | C13—C14—H14 | 119.5 |
C4—C5—N1 | 105.6 (2) | C16—C15—C14 | 119.2 (3) |
C4—C5—C13 | 133.5 (3) | C16—C15—H15 | 120.4 |
N1—C5—C13 | 120.9 (2) | C14—C15—H15 | 120.4 |
O1—C6—C4 | 118.8 (3) | C15—C16—C17 | 121.6 (3) |
O1—C6—C7 | 120.3 (3) | C15—C16—Cl1 | 119.1 (2) |
C4—C6—C7 | 120.8 (2) | C17—C16—Cl1 | 119.3 (2) |
C8—C7—C12 | 118.8 (3) | C18—C17—C16 | 118.7 (3) |
C8—C7—C6 | 122.4 (3) | C18—C17—H17 | 120.6 |
C12—C7—C6 | 118.5 (3) | C16—C17—H17 | 120.6 |
C9—C8—C7 | 120.9 (3) | C17—C18—C13 | 121.7 (3) |
C9—C8—H8 | 119.5 | C17—C18—H18 | 119.2 |
C7—C8—H8 | 119.5 | C13—C18—H18 | 119.2 |
C10—C9—C8 | 120.5 (3) | S1—C19—H19A | 109.5 |
C10—C9—H9 | 119.8 | S1—C19—H19B | 109.5 |
C8—C9—H9 | 119.8 | H19A—C19—H19B | 109.5 |
C9—C10—C11 | 119.9 (3) | S1—C19—H19C | 109.5 |
C9—C10—H10 | 120.1 | H19A—C19—H19C | 109.5 |
C11—C10—H10 | 120.1 | H19B—C19—H19C | 109.5 |
C10—C11—C12 | 120.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N3i | 0.86 (3) | 2.09 (3) | 2.952 (3) | 172 (3) |
Symmetry code: (i) x, −y+3/2, z−1/2. |