Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035635/dn2220sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035635/dn2220Isup2.hkl |
CCDC reference: 657865
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.116
- Data-to-parameter ratio = 18.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 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 0 ALERT type 5 Informative message, check
For general background, see: Dridi et al. (1998); El Efrit et al. (1996); Gorczynski et al. (2004); Wipf et al. (2001). For structural information, see: Allen (2002); Etter et al. (1990); Bernstein et al. (1995).
To the suspension of sodium hydride (20 mmol) in THF (50 ml) was added drop wise under nitrogen atmosphere with stirring at room temperature a solution of N-thiocarbamoylimidate: Ph—C(OMe)=N—C(NHPh)=S (10 mmol) in THF (10 ml). After stirring for 1 h, 2-Bromo-1-phenylethanone (10 mmol) dissolved in THF (30 ml) was added. The reaction mixture was stirred for a period of 14 h and hydrolyzed with water (10 ml). The organic layer was extracted with chloroform, dried over MgSO4 and concentrated under reduced pressure to give the 5-Benzoyl-2-phenylamino-4-phenylthiazole. Recristallization from water-ethanol (2:1) afford crystals (mp 473 K) suitable for x-ray diffraction study.
Aryl H atoms were positioned geometrically and refined using a riding model, with C—H = 0.96 Å. whereas the H atom of the NH groups was found in difference fourier maps.
Aminothiazoles constitute excellent precursors of a large variety of biologically active compounds such as inihibitors of human breast cancer cell proliferation (Gorczynski et al., 2004) and as inhibitors of protein phosphatases (Wipf et al., 2001). As a part of our ongoing research focused on the use of N-functionalized imidates in heterocyclic syntheses (El Efrit et al., 1996, Dridi et al., 1998), we show that, in presence of sodium hydride (NaH), the reaction of N-thiocarbamoylimidate, Ph—C(OMe)=N—C(NHPh)=S, with 2-Bromo-1-phenylethanone (Br—CH2—C(O)—Ph) can can theoretically lead to thiazole or diazole isomeric ring.
From the X-Ray diffraction experiment, the title compound was identified as 5-Benzoyl-2-phenylamino-4-phenylthiazole, C22H16N2OS (I).The bond lengths and bond angles observed in this structure exhibit normal values (Allen, 2002). The four rings constituting the molecule (Fig1) named A(C1, C2, C3, N1, S) for the thiazole and B(C5, C6, C7, C8, C9, C10), C(C11, C12, C13, C14, C15, C16) and D(C17, C18, C19, C20, C21, C22) for the phenyl are as expected planar with the largest deviations being 0.016\%A for the thiazole ring, but they are twisted with respect to each other. The dihedral angles between these planes are A^ B= 51,09 (5), A^D = 55,93 (6), AĈ = 49,99 (7), B^ = 45,51 (7), B^D = 33,57 (8) and C^D = 15,82 (13).
The molecules are organized by pairs forming dimer through N—H···N hydrogen bonds building a graph set motif R22(8) (Etter et al., 1990; Bernstein et al., 1995) (Table 1, Fig. 2). The packing is stabilized by van der Waals interactions.
For general background, see: Dridi et al. (1998); El Efrit et al. (1996); Gorczynski et al. (2004); Wipf et al. (2001). For structural information, see: Allen (2002); Etter et al. (1990); Bernstein et al. (1995).
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 PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).
C22H16N2OS | F(000) = 744 |
Mr = 356.43 | Dx = 1.330 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 13.163 (4) Å | θ = 9–11° |
b = 9.433 (4) Å | µ = 0.20 mm−1 |
c = 14.533 (2) Å | T = 293 K |
β = 99.33 (2)° | Prism, colourless |
V = 1780.7 (10) Å3 | 0.20 × 0.18 × 0.16 mm |
Z = 4 |
Enraf–Nonius MACH3 diffractometer | Rint = 0.028 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 2.3° |
Graphite monochromator | h = −17→17 |
non–profiled ω scans | k = 0→12 |
6093 measured reflections | l = −5→19 |
4298 independent reflections | 2 standard reflections every 120 min |
2704 reflections with I > 2σ(I) | intensity decay: 4% |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0501P)2 + 0.2524P] where P = (Fo2 + 2Fc2)/3 |
4298 reflections | (Δ/σ)max = 0.014 |
239 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C22H16N2OS | V = 1780.7 (10) Å3 |
Mr = 356.43 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.163 (4) Å | µ = 0.20 mm−1 |
b = 9.433 (4) Å | T = 293 K |
c = 14.533 (2) Å | 0.20 × 0.18 × 0.16 mm |
β = 99.33 (2)° |
Enraf–Nonius MACH3 diffractometer | Rint = 0.028 |
6093 measured reflections | 2 standard reflections every 120 min |
4298 independent reflections | intensity decay: 4% |
2704 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.17 e Å−3 |
4298 reflections | Δρmin = −0.27 e Å−3 |
239 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 | ||
H23 | 0.4049 (15) | 0.014 (2) | 0.5334 (15) | 0.051 (6)* | |
S1 | 0.45331 (4) | 0.35859 (5) | 0.61163 (4) | 0.04442 (15) | |
N1 | 0.55404 (11) | 0.16658 (16) | 0.53728 (11) | 0.0406 (4) | |
N2 | 0.38926 (12) | 0.09407 (19) | 0.55532 (13) | 0.0474 (4) | |
C1 | 0.46481 (13) | 0.19246 (19) | 0.56396 (13) | 0.0393 (4) | |
C2 | 0.61980 (13) | 0.2793 (2) | 0.55837 (13) | 0.0393 (4) | |
C3 | 0.58128 (13) | 0.3926 (2) | 0.60089 (14) | 0.0419 (5) | |
C4 | 0.62158 (16) | 0.5284 (2) | 0.63774 (14) | 0.0485 (5) | |
C5 | 0.73535 (16) | 0.5524 (2) | 0.66124 (14) | 0.0473 (5) | |
C6 | 0.77439 (18) | 0.6847 (2) | 0.64381 (15) | 0.0582 (6) | |
H6 | 0.7307 | 0.7557 | 0.6163 | 0.070* | |
C7 | 0.8793 (2) | 0.7100 (3) | 0.66781 (18) | 0.0721 (8) | |
H7 | 0.9059 | 0.7980 | 0.6553 | 0.087* | |
C8 | 0.9439 (2) | 0.6068 (3) | 0.70969 (19) | 0.0771 (8) | |
H8 | 1.0141 | 0.6246 | 0.7247 | 0.093* | |
C9 | 0.90544 (18) | 0.4770 (3) | 0.72957 (17) | 0.0698 (7) | |
H9 | 0.9491 | 0.4080 | 0.7597 | 0.084* | |
C10 | 0.80140 (17) | 0.4493 (3) | 0.70459 (15) | 0.0557 (6) | |
H10 | 0.7756 | 0.3608 | 0.7170 | 0.067* | |
C11 | 0.30362 (13) | 0.0973 (2) | 0.60371 (14) | 0.0431 (5) | |
C12 | 0.28562 (15) | −0.0198 (2) | 0.65595 (15) | 0.0549 (6) | |
H12 | 0.3287 | −0.0984 | 0.6588 | 0.066* | |
C13 | 0.20274 (18) | −0.0194 (3) | 0.70408 (17) | 0.0692 (7) | |
H13 | 0.1900 | −0.0985 | 0.7387 | 0.083* | |
C14 | 0.13943 (16) | 0.0965 (3) | 0.70108 (17) | 0.0674 (7) | |
H14 | 0.0850 | 0.0968 | 0.7347 | 0.081* | |
C15 | 0.15660 (15) | 0.2113 (3) | 0.64847 (17) | 0.0606 (6) | |
H15 | 0.1134 | 0.2897 | 0.6461 | 0.073* | |
C16 | 0.23814 (14) | 0.2122 (2) | 0.59834 (15) | 0.0502 (5) | |
H16 | 0.2484 | 0.2898 | 0.5615 | 0.060* | |
C17 | 0.72450 (13) | 0.2650 (2) | 0.53328 (13) | 0.0408 (4) | |
C18 | 0.76104 (16) | 0.3639 (2) | 0.47657 (16) | 0.0547 (5) | |
H18 | 0.7196 | 0.4392 | 0.4523 | 0.066* | |
C19 | 0.85990 (18) | 0.3503 (3) | 0.45611 (18) | 0.0711 (7) | |
H19 | 0.8847 | 0.4172 | 0.4183 | 0.085* | |
C20 | 0.92083 (17) | 0.2400 (3) | 0.49075 (19) | 0.0731 (7) | |
H20 | 0.9870 | 0.2318 | 0.4767 | 0.088* | |
C21 | 0.88460 (16) | 0.1402 (3) | 0.54673 (18) | 0.0671 (7) | |
H21 | 0.9266 | 0.0652 | 0.5706 | 0.080* | |
C22 | 0.78631 (15) | 0.1514 (2) | 0.56741 (15) | 0.0520 (5) | |
H22 | 0.7615 | 0.0830 | 0.6042 | 0.062* | |
O1 | 0.56177 (12) | 0.62208 (16) | 0.65279 (13) | 0.0742 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0376 (2) | 0.0432 (3) | 0.0558 (3) | 0.0025 (2) | 0.0174 (2) | −0.0052 (3) |
N1 | 0.0362 (8) | 0.0400 (9) | 0.0481 (10) | −0.0007 (7) | 0.0145 (7) | −0.0031 (7) |
N2 | 0.0410 (9) | 0.0445 (10) | 0.0617 (11) | −0.0052 (7) | 0.0230 (8) | −0.0115 (9) |
C1 | 0.0374 (9) | 0.0407 (10) | 0.0422 (11) | 0.0026 (8) | 0.0134 (8) | −0.0002 (9) |
C2 | 0.0365 (9) | 0.0427 (10) | 0.0406 (10) | 0.0014 (8) | 0.0117 (8) | 0.0032 (9) |
C3 | 0.0352 (9) | 0.0443 (11) | 0.0482 (11) | −0.0001 (8) | 0.0127 (8) | −0.0010 (9) |
C4 | 0.0529 (12) | 0.0457 (11) | 0.0504 (12) | −0.0044 (9) | 0.0191 (10) | −0.0063 (10) |
C5 | 0.0546 (12) | 0.0509 (12) | 0.0397 (11) | −0.0114 (10) | 0.0170 (10) | −0.0102 (10) |
C6 | 0.0714 (15) | 0.0546 (13) | 0.0521 (14) | −0.0146 (11) | 0.0207 (12) | −0.0103 (11) |
C7 | 0.0790 (18) | 0.0737 (17) | 0.0692 (17) | −0.0358 (15) | 0.0286 (15) | −0.0197 (14) |
C8 | 0.0570 (14) | 0.107 (2) | 0.0690 (17) | −0.0226 (15) | 0.0163 (13) | −0.0289 (17) |
C9 | 0.0598 (15) | 0.0902 (19) | 0.0570 (15) | −0.0034 (14) | 0.0024 (12) | −0.0135 (14) |
C10 | 0.0585 (13) | 0.0642 (14) | 0.0458 (12) | −0.0083 (11) | 0.0124 (10) | −0.0024 (11) |
C11 | 0.0331 (9) | 0.0540 (12) | 0.0441 (11) | −0.0052 (8) | 0.0118 (8) | −0.0067 (10) |
C12 | 0.0452 (11) | 0.0633 (14) | 0.0579 (13) | 0.0009 (10) | 0.0136 (10) | 0.0066 (11) |
C13 | 0.0579 (14) | 0.0921 (19) | 0.0614 (15) | −0.0082 (14) | 0.0215 (12) | 0.0202 (14) |
C14 | 0.0439 (12) | 0.105 (2) | 0.0586 (14) | −0.0058 (13) | 0.0232 (11) | −0.0032 (15) |
C15 | 0.0382 (11) | 0.0757 (16) | 0.0706 (16) | 0.0028 (11) | 0.0165 (11) | −0.0123 (13) |
C16 | 0.0410 (10) | 0.0538 (12) | 0.0576 (13) | −0.0037 (9) | 0.0138 (10) | −0.0061 (11) |
C17 | 0.0335 (9) | 0.0454 (11) | 0.0452 (11) | −0.0011 (8) | 0.0112 (8) | −0.0045 (9) |
C18 | 0.0515 (11) | 0.0543 (12) | 0.0628 (14) | 0.0011 (10) | 0.0229 (11) | 0.0072 (12) |
C19 | 0.0593 (14) | 0.0791 (17) | 0.0835 (18) | −0.0054 (13) | 0.0375 (13) | 0.0095 (15) |
C20 | 0.0392 (11) | 0.097 (2) | 0.0884 (19) | 0.0019 (13) | 0.0263 (12) | −0.0029 (17) |
C21 | 0.0428 (11) | 0.0779 (16) | 0.0802 (17) | 0.0152 (12) | 0.0090 (12) | 0.0066 (15) |
C22 | 0.0427 (10) | 0.0573 (13) | 0.0570 (13) | 0.0026 (10) | 0.0111 (10) | 0.0042 (11) |
O1 | 0.0654 (10) | 0.0550 (10) | 0.1070 (14) | 0.0013 (8) | 0.0286 (10) | −0.0236 (10) |
S1—C1 | 1.730 (2) | C11—C16 | 1.380 (3) |
S1—C3 | 1.7465 (18) | C11—C12 | 1.382 (3) |
N1—C1 | 1.318 (2) | C12—C13 | 1.388 (3) |
N1—C2 | 1.374 (2) | C12—H12 | 0.9300 |
N2—C1 | 1.351 (2) | C13—C14 | 1.371 (3) |
N2—C11 | 1.423 (2) | C13—H13 | 0.9300 |
N2—H23 | 0.86 (2) | C14—C15 | 1.366 (3) |
C2—C3 | 1.372 (3) | C14—H14 | 0.9300 |
C2—C17 | 1.488 (2) | C15—C16 | 1.392 (3) |
C3—C4 | 1.456 (3) | C15—H15 | 0.9300 |
C4—O1 | 1.226 (2) | C16—H16 | 0.9300 |
C4—C5 | 1.498 (3) | C17—C18 | 1.382 (3) |
C5—C10 | 1.386 (3) | C17—C22 | 1.387 (3) |
C5—C6 | 1.388 (3) | C18—C19 | 1.387 (3) |
C6—C7 | 1.389 (3) | C18—H18 | 0.9300 |
C6—H6 | 0.9300 | C19—C20 | 1.360 (3) |
C7—C8 | 1.369 (4) | C19—H19 | 0.9300 |
C7—H7 | 0.9300 | C20—C21 | 1.379 (3) |
C8—C9 | 1.374 (4) | C20—H20 | 0.9300 |
C8—H8 | 0.9300 | C21—C22 | 1.379 (3) |
C9—C10 | 1.383 (3) | C21—H21 | 0.9300 |
C9—H9 | 0.9300 | C22—H22 | 0.9300 |
C10—H10 | 0.9300 | ||
C1—S1—C3 | 88.98 (9) | C16—C11—N2 | 121.77 (19) |
C1—N1—C2 | 110.51 (15) | C12—C11—N2 | 118.35 (18) |
C1—N2—C11 | 124.74 (17) | C11—C12—C13 | 119.5 (2) |
C1—N2—H23 | 114.9 (13) | C11—C12—H12 | 120.2 |
C11—N2—H23 | 117.4 (14) | C13—C12—H12 | 120.2 |
N1—C1—N2 | 121.53 (17) | C14—C13—C12 | 120.6 (2) |
N1—C1—S1 | 115.19 (14) | C14—C13—H13 | 119.7 |
N2—C1—S1 | 123.27 (14) | C12—C13—H13 | 119.7 |
C3—C2—N1 | 115.96 (15) | C15—C14—C13 | 119.7 (2) |
C3—C2—C17 | 127.27 (17) | C15—C14—H14 | 120.2 |
N1—C2—C17 | 116.77 (16) | C13—C14—H14 | 120.2 |
C2—C3—C4 | 135.42 (17) | C14—C15—C16 | 120.6 (2) |
C2—C3—S1 | 109.24 (14) | C14—C15—H15 | 119.7 |
C4—C3—S1 | 115.35 (14) | C16—C15—H15 | 119.7 |
O1—C4—C3 | 119.58 (19) | C11—C16—C15 | 119.6 (2) |
O1—C4—C5 | 119.83 (19) | C11—C16—H16 | 120.2 |
C3—C4—C5 | 120.54 (18) | C15—C16—H16 | 120.2 |
C10—C5—C6 | 119.4 (2) | C18—C17—C22 | 119.60 (18) |
C10—C5—C4 | 121.85 (19) | C18—C17—C2 | 120.71 (18) |
C6—C5—C4 | 118.7 (2) | C22—C17—C2 | 119.69 (17) |
C5—C6—C7 | 119.4 (2) | C17—C18—C19 | 119.6 (2) |
C5—C6—H6 | 120.3 | C17—C18—H18 | 120.2 |
C7—C6—H6 | 120.3 | C19—C18—H18 | 120.2 |
C8—C7—C6 | 120.7 (2) | C20—C19—C18 | 120.6 (2) |
C8—C7—H7 | 119.7 | C20—C19—H19 | 119.7 |
C6—C7—H7 | 119.7 | C18—C19—H19 | 119.7 |
C7—C8—C9 | 120.2 (2) | C19—C20—C21 | 120.1 (2) |
C7—C8—H8 | 119.9 | C19—C20—H20 | 120.0 |
C9—C8—H8 | 119.9 | C21—C20—H20 | 120.0 |
C8—C9—C10 | 119.7 (3) | C20—C21—C22 | 120.2 (2) |
C8—C9—H9 | 120.1 | C20—C21—H21 | 119.9 |
C10—C9—H9 | 120.1 | C22—C21—H21 | 119.9 |
C9—C10—C5 | 120.5 (2) | C21—C22—C17 | 119.9 (2) |
C9—C10—H10 | 119.7 | C21—C22—H22 | 120.1 |
C5—C10—H10 | 119.7 | C17—C22—H22 | 120.1 |
C16—C11—C12 | 119.87 (18) | ||
C2—N1—C1—N2 | −176.33 (18) | C7—C8—C9—C10 | 1.9 (4) |
C2—N1—C1—S1 | 2.8 (2) | C8—C9—C10—C5 | −1.2 (3) |
C11—N2—C1—N1 | 162.18 (19) | C6—C5—C10—C9 | −0.6 (3) |
C11—N2—C1—S1 | −16.8 (3) | C4—C5—C10—C9 | −176.8 (2) |
C3—S1—C1—N1 | −3.38 (16) | C1—N2—C11—C16 | 55.9 (3) |
C3—S1—C1—N2 | 175.70 (18) | C1—N2—C11—C12 | −125.2 (2) |
C1—N1—C2—C3 | −0.3 (2) | C16—C11—C12—C13 | −1.3 (3) |
C1—N1—C2—C17 | 179.33 (16) | N2—C11—C12—C13 | 179.8 (2) |
N1—C2—C3—C4 | 177.6 (2) | C11—C12—C13—C14 | −0.7 (4) |
C17—C2—C3—C4 | −2.1 (4) | C12—C13—C14—C15 | 1.5 (4) |
N1—C2—C3—S1 | −2.1 (2) | C13—C14—C15—C16 | −0.4 (4) |
C17—C2—C3—S1 | 178.25 (16) | C12—C11—C16—C15 | 2.4 (3) |
C1—S1—C3—C2 | 2.93 (15) | N2—C11—C16—C15 | −178.74 (19) |
C1—S1—C3—C4 | −176.84 (16) | C14—C15—C16—C11 | −1.6 (3) |
C2—C3—C4—O1 | 163.3 (2) | C3—C2—C17—C18 | −56.6 (3) |
S1—C3—C4—O1 | −17.0 (3) | N1—C2—C17—C18 | 123.8 (2) |
C2—C3—C4—C5 | −19.4 (4) | C3—C2—C17—C22 | 123.2 (2) |
S1—C3—C4—C5 | 160.29 (15) | N1—C2—C17—C22 | −56.4 (3) |
O1—C4—C5—C10 | 136.6 (2) | C22—C17—C18—C19 | −1.4 (3) |
C3—C4—C5—C10 | −40.7 (3) | C2—C17—C18—C19 | 178.4 (2) |
O1—C4—C5—C6 | −39.6 (3) | C17—C18—C19—C20 | 0.5 (4) |
C3—C4—C5—C6 | 143.1 (2) | C18—C19—C20—C21 | 0.1 (4) |
C10—C5—C6—C7 | 1.7 (3) | C19—C20—C21—C22 | 0.3 (4) |
C4—C5—C6—C7 | 178.04 (19) | C20—C21—C22—C17 | −1.3 (4) |
C5—C6—C7—C8 | −1.0 (4) | C18—C17—C22—C21 | 1.8 (3) |
C6—C7—C8—C9 | −0.8 (4) | C2—C17—C22—C21 | −178.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H23···N1i | 0.858 (19) | 2.10 (2) | 2.956 (3) | 172 (2) |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C22H16N2OS |
Mr | 356.43 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 13.163 (4), 9.433 (4), 14.533 (2) |
β (°) | 99.33 (2) |
V (Å3) | 1780.7 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.20 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Enraf–Nonius MACH3 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6093, 4298, 2704 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.660 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.116, 1.00 |
No. of reflections | 4298 |
No. of parameters | 239 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.27 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H23···N1i | 0.858 (19) | 2.10 (2) | 2.956 (3) | 172 (2) |
Symmetry code: (i) −x+1, −y, −z+1. |
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Aminothiazoles constitute excellent precursors of a large variety of biologically active compounds such as inihibitors of human breast cancer cell proliferation (Gorczynski et al., 2004) and as inhibitors of protein phosphatases (Wipf et al., 2001). As a part of our ongoing research focused on the use of N-functionalized imidates in heterocyclic syntheses (El Efrit et al., 1996, Dridi et al., 1998), we show that, in presence of sodium hydride (NaH), the reaction of N-thiocarbamoylimidate, Ph—C(OMe)=N—C(NHPh)=S, with 2-Bromo-1-phenylethanone (Br—CH2—C(O)—Ph) can can theoretically lead to thiazole or diazole isomeric ring.
From the X-Ray diffraction experiment, the title compound was identified as 5-Benzoyl-2-phenylamino-4-phenylthiazole, C22H16N2OS (I).The bond lengths and bond angles observed in this structure exhibit normal values (Allen, 2002). The four rings constituting the molecule (Fig1) named A(C1, C2, C3, N1, S) for the thiazole and B(C5, C6, C7, C8, C9, C10), C(C11, C12, C13, C14, C15, C16) and D(C17, C18, C19, C20, C21, C22) for the phenyl are as expected planar with the largest deviations being 0.016\%A for the thiazole ring, but they are twisted with respect to each other. The dihedral angles between these planes are A^ B= 51,09 (5), A^D = 55,93 (6), AĈ = 49,99 (7), B^ = 45,51 (7), B^D = 33,57 (8) and C^D = 15,82 (13).
The molecules are organized by pairs forming dimer through N—H···N hydrogen bonds building a graph set motif R22(8) (Etter et al., 1990; Bernstein et al., 1995) (Table 1, Fig. 2). The packing is stabilized by van der Waals interactions.