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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004120/at6084sup1.cif
Contains datablocks global, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004120/at60841sup2.hkl
Contains datablock 1

CCDC reference: 601103

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.059
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C12 .. 5.42 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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

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
C17H13ClN2OSF(000) = 680
Mr = 328.81Dx = 1.388 Mg m3
Monoclinic, P21/cMelting point: 468 K
Hall symbol: -P 2ybcCu Kα radiation, λ = 1.5418 Å
a = 7.2814 (15) ÅCell parameters from 25 reflections
b = 23.650 (3) Åθ = 32–35°
c = 9.752 (5) ŵ = 3.41 mm1
β = 110.46 (3)°T = 293 K
V = 1573.4 (9) Å3Prism, colourless
Z = 40.1 × 0.1 × 0.1 mm
Data collection top
Enraf–Nonius CAD4
diffractometer
Rint = 0.056
Radiation source: Enraf–Nonius FR590θmax = 74.9°, θmin = 3.7°
Graphite monochromatorh = 98
Non–profiled ω scansk = 029
3236 measured reflectionsl = 012
3236 independent reflections1 standard reflections every 120 min
1639 reflections with I > 2σ(I) intensity decay: 2%
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H 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 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.21 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.14922 (14)0.69610 (4)0.62147 (9)0.0644 (3)
Cl11.06895 (13)0.93313 (4)0.41461 (8)0.0783 (3)
O10.5764 (3)0.84701 (8)1.03731 (18)0.0608 (6)
N10.4198 (4)0.76941 (10)0.5930 (3)0.0399 (6)
H10.396 (4)0.7530 (12)0.509 (3)0.085 (12)*
C20.3181 (4)0.75069 (11)0.6784 (3)0.0417 (7)
N30.3643 (3)0.77929 (9)0.8026 (2)0.0392 (6)
C40.4973 (4)0.82006 (11)0.7940 (3)0.0353 (7)
C50.5366 (4)0.81356 (11)0.6666 (3)0.0382 (7)
C60.5650 (4)0.86158 (12)0.9144 (3)0.0413 (7)
C70.6097 (4)0.92065 (11)0.8860 (3)0.0386 (7)
C80.5232 (4)0.94639 (12)0.7513 (3)0.0460 (8)
H80.44130.92540.67300.055*
C90.5566 (5)1.00231 (13)0.7315 (4)0.0616 (10)
H90.49801.01890.64000.074*
C100.6754 (5)1.03391 (13)0.8450 (4)0.0713 (11)
H100.69811.07180.83070.086*
C110.7613 (5)1.00965 (14)0.9807 (4)0.0661 (10)
H110.84161.03131.05810.079*
C120.7289 (4)0.95296 (13)1.0030 (3)0.0566 (9)
H120.78630.93681.09500.068*
C130.6707 (4)0.84184 (11)0.6065 (3)0.0368 (7)
C140.6148 (4)0.85090 (11)0.4555 (3)0.0439 (8)
H140.49300.83830.39370.053*
C150.7378 (4)0.87818 (12)0.3971 (3)0.0484 (8)
H150.70030.88360.29650.058*
C160.9154 (4)0.89715 (13)0.4886 (3)0.0495 (8)
C170.9765 (4)0.88870 (12)0.6380 (3)0.0529 (9)
H171.09830.90170.69880.064*
C180.8542 (4)0.86087 (12)0.6948 (3)0.0440 (7)
H180.89530.85460.79520.053*
C190.0096 (5)0.70910 (13)0.7355 (3)0.0882 (12)
H19A0.01330.74900.73850.132*
H19B0.08030.69570.83260.132*
H19C0.11360.68970.69690.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0885 (7)0.0512 (5)0.0530 (5)0.0279 (5)0.0241 (5)0.0105 (5)
Cl10.0735 (6)0.1121 (8)0.0561 (5)0.0308 (6)0.0314 (5)0.0028 (6)
O10.0996 (18)0.0555 (14)0.0259 (11)0.0144 (13)0.0203 (11)0.0011 (10)
N10.0569 (17)0.0325 (14)0.0342 (14)0.0024 (13)0.0207 (13)0.0015 (12)
C20.060 (2)0.0304 (16)0.0359 (17)0.0023 (15)0.0189 (15)0.0013 (13)
N30.0569 (16)0.0345 (14)0.0293 (12)0.0070 (12)0.0190 (11)0.0006 (11)
C40.0455 (18)0.0314 (16)0.0296 (15)0.0057 (13)0.0137 (13)0.0020 (12)
C50.0470 (19)0.0335 (17)0.0364 (16)0.0011 (14)0.0174 (14)0.0003 (13)
C60.0474 (19)0.0441 (19)0.0351 (16)0.0033 (16)0.0178 (14)0.0053 (15)
C70.0446 (18)0.0379 (18)0.0359 (16)0.0071 (14)0.0175 (13)0.0129 (14)
C80.056 (2)0.0369 (17)0.0493 (18)0.0046 (15)0.0238 (15)0.0022 (15)
C90.087 (3)0.040 (2)0.069 (2)0.002 (2)0.041 (2)0.0043 (18)
C100.095 (3)0.035 (2)0.100 (3)0.014 (2)0.053 (3)0.004 (2)
C110.076 (3)0.056 (2)0.071 (3)0.026 (2)0.031 (2)0.028 (2)
C120.061 (2)0.056 (2)0.053 (2)0.0161 (18)0.0199 (17)0.0101 (18)
C130.0471 (18)0.0361 (16)0.0327 (15)0.0025 (15)0.0208 (13)0.0002 (14)
C140.0495 (19)0.051 (2)0.0299 (15)0.0069 (16)0.0124 (13)0.0031 (14)
C150.059 (2)0.057 (2)0.0335 (17)0.0020 (17)0.0221 (15)0.0007 (15)
C160.046 (2)0.067 (2)0.0397 (17)0.0029 (17)0.0203 (15)0.0010 (17)
C170.046 (2)0.069 (2)0.0448 (18)0.0056 (18)0.0168 (15)0.0039 (17)
C180.0444 (18)0.056 (2)0.0309 (15)0.0027 (16)0.0114 (13)0.0031 (15)
C190.080 (3)0.076 (3)0.120 (3)0.032 (2)0.050 (2)0.024 (3)
Geometric parameters (Å, º) top
S1—C21.735 (3)C10—C111.375 (4)
S1—C191.776 (3)C10—H100.9300
Cl1—C161.749 (3)C11—C121.391 (4)
O1—C61.221 (3)C11—H110.9300
N1—C21.367 (3)C12—H120.9300
N1—C51.379 (3)C13—C181.387 (3)
N1—H10.86 (3)C13—C141.400 (3)
C2—N31.324 (3)C14—C151.378 (3)
N3—C41.390 (3)C14—H140.9300
C4—C51.378 (3)C15—C161.365 (3)
C4—C61.477 (3)C15—H150.9300
C5—C131.465 (3)C16—C171.381 (3)
C6—C71.482 (3)C17—C181.370 (3)
C7—C81.384 (3)C17—H170.9300
C7—C121.395 (3)C18—H180.9300
C8—C91.371 (3)C19—H19A0.9600
C8—H80.9300C19—H19B0.9600
C9—C101.365 (4)C19—H19C0.9600
C9—H90.9300
C2—S1—C1999.66 (14)C10—C11—H11119.8
C2—N1—C5107.2 (2)C12—C11—H11119.8
C2—N1—H1117 (2)C11—C12—C7119.4 (3)
C5—N1—H1136 (2)C11—C12—H12120.3
N3—C2—N1111.9 (3)C7—C12—H12120.3
N3—C2—S1126.7 (2)C18—C13—C14117.8 (3)
N1—C2—S1121.4 (2)C18—C13—C5122.1 (2)
C2—N3—C4105.0 (2)C14—C13—C5120.1 (3)
C5—C4—N3110.2 (2)C15—C14—C13121.0 (3)
C5—C4—C6132.4 (3)C15—C14—H14119.5
N3—C4—C6117.4 (2)C13—C14—H14119.5
C4—C5—N1105.6 (2)C16—C15—C14119.2 (3)
C4—C5—C13133.5 (3)C16—C15—H15120.4
N1—C5—C13120.9 (2)C14—C15—H15120.4
O1—C6—C4118.8 (3)C15—C16—C17121.6 (3)
O1—C6—C7120.3 (3)C15—C16—Cl1119.1 (2)
C4—C6—C7120.8 (2)C17—C16—Cl1119.3 (2)
C8—C7—C12118.8 (3)C18—C17—C16118.7 (3)
C8—C7—C6122.4 (3)C18—C17—H17120.6
C12—C7—C6118.5 (3)C16—C17—H17120.6
C9—C8—C7120.9 (3)C17—C18—C13121.7 (3)
C9—C8—H8119.5C17—C18—H18119.2
C7—C8—H8119.5C13—C18—H18119.2
C10—C9—C8120.5 (3)S1—C19—H19A109.5
C10—C9—H9119.8S1—C19—H19B109.5
C8—C9—H9119.8H19A—C19—H19B109.5
C9—C10—C11119.9 (3)S1—C19—H19C109.5
C9—C10—H10120.1H19A—C19—H19C109.5
C11—C10—H10120.1H19B—C19—H19C109.5
C10—C11—C12120.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N3i0.86 (3)2.09 (3)2.952 (3)172 (3)
Symmetry code: (i) x, y+3/2, z1/2.
 

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