Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034939/ci2412sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034939/ci2412Isup2.hkl |
CCDC reference: 657823
The title compound was prepared according to the literature method (Furlenmeier et al., 1987). Crystals suitable for X-ray analysis were obtained by slow evaporation of a ethanol solution at room temperature (m.p. 471–473 K).
The tert-butyl group is disordered over two positions, with refined occupations 0.63 (4) and 0.37 (4). The C—C distances of the tert-butyl groups were restrained to 1.53 (1) Å, and the C—O and C···C distances involving disordered C-atoms were restrained to be equal. O– and N-bound H atoms were located from a difference Fourier map, and refined freely. C-bound H atoms were positioned geometrically (C—H = 0.94 or 0.97 Å) and refined using a riding model, with Uiso(H) = 1.2–1.5Ueq(C).
2-Aminothiazole compounds have been extensively studied because of their biological and industrial applications (Lynch et al., 1999; Toplak et al., 2003). A search of the Cambridge Structural Database (CSD, Version 5.28 of May 2007) reveals that there are 127 crystal structures containing the 2-aminothiazole moiety. The title compound is a very important intermediate of ceftazidime, which is among the most important cephalosporin antibiotics (Powers et al., 2001). Crystal structures of some cephalosporin intermediates which contain a 2-aminothiazole group have been reported (Yoshida et al., 1989; Laurent et al., 1981). The title compound can give a reactive intermediate by reaction with diethylenetriamine-N,N,N',N'',N''- pentaacetic acid (DTPA), further, which can be used to prepare a protein-chelator conjugate (Johnson, 1999). We report here the crystal structure of the title compound.
The thiazole ring is planar to within ±0.006 (1) Å. The amino group is coplanar with the thiazole ring, with atom N3 deviating from the thiazole plane by -0.021 (2) Å. The O1/N1/C1/C2/C5/C6/C10 plane is twisted away from the thiazole plane by 21.92 (8)°. The tert-butyl group is disordered over two positions, with occupancies of 0.63 (4) and 0.37 (4). The carboxylate plane (C1/C5/O4/O5) is nearly perpendicular to the thiazole ring (dihedral angle 86.9 (1)°).
The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen bonds (Table 1) involving the O atoms of the water molecules and carboxylate groups. These hydrogen bonds link the molecules into a two-dimensional network parallel to the (001) plane (Fig. 2). The thiazole rings of the inversion-related molecules at (x, y, z) and (1 - x, 1 - y, 1 - z) are stacked with their centroids separated by a distance of 3.5387 (10) Å, indicating π-π interactions.
For synthesis, see: Furlenmeier et al. (1987); For general background, see: David (1999); Lynch et al. (1999); Rachel et al. (2001); Toplak et al. (2003). For related structures, see: Laurent et al. (1981); Yoshida et al. (1989).
Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
C13H19N3O5S·H2O | F(000) = 1472 |
Mr = 347.39 | Dx = 1.304 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 31871 reflections |
a = 12.7918 (17) Å | θ = 3.2–25.4° |
b = 12.2489 (15) Å | µ = 0.21 mm−1 |
c = 22.595 (3) Å | T = 223 K |
V = 3540.2 (8) Å3 | Block, colourless |
Z = 8 | 0.80 × 0.80 × 0.57 mm |
Rigaku Mercury diffractometer | 3232 independent reflections |
Radiation source: fine-focus sealed tube | 3096 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.4°, θmin = 3.2° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −14→14 |
Tmin = 0.847, Tmax = 0.888 | l = −27→26 |
31871 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0297P)2 + 2.4239P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
3232 reflections | Δρmax = 0.20 e Å−3 |
268 parameters | Δρmin = −0.28 e Å−3 |
22 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0151 (7) |
C13H19N3O5S·H2O | V = 3540.2 (8) Å3 |
Mr = 347.39 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 12.7918 (17) Å | µ = 0.21 mm−1 |
b = 12.2489 (15) Å | T = 223 K |
c = 22.595 (3) Å | 0.80 × 0.80 × 0.57 mm |
Rigaku Mercury diffractometer | 3232 independent reflections |
Absorption correction: multi-scan (Jacobson, 1998) | 3096 reflections with I > 2σ(I) |
Tmin = 0.847, Tmax = 0.888 | Rint = 0.031 |
31871 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 22 restraints |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.20 e Å−3 |
3232 reflections | Δρmin = −0.28 e Å−3 |
268 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 | Occ. (<1) | |
S1 | 0.46180 (4) | 0.52078 (4) | 0.40564 (2) | 0.03825 (17) | |
O1 | 0.41053 (8) | 0.12570 (9) | 0.56784 (5) | 0.0286 (3) | |
O2 | 0.47558 (11) | 0.23610 (12) | 0.66636 (6) | 0.0455 (4) | |
O3 | 0.61809 (11) | 0.13114 (11) | 0.67241 (6) | 0.0466 (4) | |
O4 | 0.24960 (11) | 0.16967 (14) | 0.45102 (7) | 0.0585 (4) | |
O5 | 0.21461 (9) | 0.25993 (12) | 0.53369 (6) | 0.0448 (4) | |
O6 | 0.29085 (12) | 0.33757 (12) | 0.63821 (7) | 0.0406 (3) | |
N1 | 0.45637 (10) | 0.20940 (11) | 0.53363 (6) | 0.0268 (3) | |
N2 | 0.53804 (11) | 0.35198 (12) | 0.45411 (6) | 0.0276 (3) | |
N3 | 0.66501 (12) | 0.46234 (15) | 0.40943 (8) | 0.0377 (4) | |
C1 | 0.38961 (12) | 0.25548 (14) | 0.49967 (7) | 0.0263 (4) | |
C2 | 0.49082 (13) | 0.07540 (14) | 0.60427 (8) | 0.0290 (4) | |
C3 | 0.52641 (13) | 0.15890 (14) | 0.65053 (8) | 0.0297 (4) | |
C5 | 0.27385 (13) | 0.22507 (14) | 0.49359 (8) | 0.0314 (4) | |
C6 | 0.43082 (12) | 0.34460 (14) | 0.46353 (7) | 0.0271 (4) | |
C7 | 0.56742 (13) | 0.43966 (14) | 0.42388 (7) | 0.0291 (4) | |
C8 | 0.37851 (14) | 0.42879 (15) | 0.43978 (8) | 0.0360 (4) | |
H8 | 0.3055 | 0.4369 | 0.4415 | 0.043* | |
C9 | 0.58029 (15) | 0.03195 (17) | 0.56715 (9) | 0.0412 (5) | |
H9A | 0.5534 | −0.0193 | 0.5382 | 0.062* | |
H9B | 0.6303 | −0.0048 | 0.5926 | 0.062* | |
H9C | 0.6144 | 0.0921 | 0.5470 | 0.062* | |
C10 | 0.43324 (17) | −0.01592 (17) | 0.63619 (10) | 0.0488 (6) | |
H10A | 0.3749 | 0.0144 | 0.6581 | 0.073* | |
H10B | 0.4806 | −0.0521 | 0.6633 | 0.073* | |
H10C | 0.4075 | −0.0683 | 0.6075 | 0.073* | |
C4 | 0.6558 (15) | 0.1863 (12) | 0.7277 (6) | 0.043 (4) | 0.37 (4) |
C11 | 0.5784 (18) | 0.1947 (19) | 0.7785 (11) | 0.065 (4) | 0.37 (4) |
H11A | 0.5607 | 0.1221 | 0.7924 | 0.098* | 0.37 (4) |
H11B | 0.5156 | 0.2314 | 0.7650 | 0.098* | 0.37 (4) |
H11C | 0.6095 | 0.2361 | 0.8106 | 0.098* | 0.37 (4) |
C12 | 0.695 (2) | 0.2988 (16) | 0.7095 (11) | 0.067 (5) | 0.37 (4) |
H12A | 0.7427 | 0.2916 | 0.6764 | 0.100* | 0.37 (4) |
H12B | 0.7307 | 0.3327 | 0.7425 | 0.100* | 0.37 (4) |
H12C | 0.6360 | 0.3438 | 0.6978 | 0.100* | 0.37 (4) |
C13 | 0.7481 (17) | 0.1146 (17) | 0.7456 (11) | 0.070 (4) | 0.37 (4) |
H13A | 0.7230 | 0.0425 | 0.7561 | 0.106* | 0.37 (4) |
H13B | 0.7834 | 0.1469 | 0.7793 | 0.106* | 0.37 (4) |
H13C | 0.7966 | 0.1089 | 0.7127 | 0.106* | 0.37 (4) |
C4' | 0.6727 (10) | 0.1936 (8) | 0.7204 (4) | 0.043 (2) | 0.63 (4) |
C11' | 0.6069 (13) | 0.1748 (14) | 0.7744 (6) | 0.072 (3) | 0.63 (4) |
H11D | 0.5892 | 0.0979 | 0.7772 | 0.108* | 0.63 (4) |
H11E | 0.5433 | 0.2176 | 0.7715 | 0.108* | 0.63 (4) |
H11F | 0.6456 | 0.1966 | 0.8093 | 0.108* | 0.63 (4) |
C12' | 0.6832 (13) | 0.3121 (8) | 0.7044 (6) | 0.063 (3) | 0.63 (4) |
H12D | 0.7190 | 0.3186 | 0.6667 | 0.095* | 0.63 (4) |
H12E | 0.7231 | 0.3495 | 0.7347 | 0.095* | 0.63 (4) |
H12F | 0.6143 | 0.3447 | 0.7013 | 0.095* | 0.63 (4) |
C13' | 0.7772 (12) | 0.1372 (13) | 0.7235 (9) | 0.088 (4) | 0.63 (4) |
H13D | 0.7667 | 0.0594 | 0.7289 | 0.132* | 0.63 (4) |
H13E | 0.8168 | 0.1660 | 0.7566 | 0.132* | 0.63 (4) |
H13F | 0.8154 | 0.1499 | 0.6871 | 0.132* | 0.63 (4) |
H6A | 0.267 (2) | 0.312 (2) | 0.6048 (12) | 0.069 (9)* | |
H6B | 0.346 (2) | 0.306 (2) | 0.6449 (12) | 0.069 (9)* | |
H2A | 0.5873 (19) | 0.3049 (19) | 0.4660 (10) | 0.054 (7)* | |
H3A | 0.6783 (17) | 0.5257 (19) | 0.3913 (10) | 0.046 (6)* | |
H3B | 0.7138 (18) | 0.4203 (19) | 0.4232 (10) | 0.052 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0322 (3) | 0.0349 (3) | 0.0477 (3) | 0.00080 (19) | −0.0030 (2) | 0.0154 (2) |
O1 | 0.0212 (6) | 0.0325 (6) | 0.0321 (6) | −0.0040 (5) | −0.0045 (5) | 0.0102 (5) |
O2 | 0.0443 (8) | 0.0477 (8) | 0.0444 (8) | 0.0147 (7) | −0.0090 (6) | −0.0099 (6) |
O3 | 0.0436 (8) | 0.0431 (8) | 0.0530 (8) | 0.0132 (6) | −0.0279 (7) | −0.0152 (7) |
O4 | 0.0320 (7) | 0.0720 (11) | 0.0715 (10) | −0.0050 (7) | −0.0118 (8) | −0.0226 (9) |
O5 | 0.0222 (6) | 0.0611 (9) | 0.0511 (8) | −0.0062 (6) | 0.0044 (6) | −0.0019 (7) |
O6 | 0.0370 (8) | 0.0379 (8) | 0.0470 (9) | 0.0070 (6) | 0.0045 (7) | 0.0071 (7) |
N1 | 0.0218 (7) | 0.0297 (7) | 0.0289 (7) | −0.0033 (6) | 0.0001 (6) | 0.0049 (6) |
N2 | 0.0204 (7) | 0.0297 (8) | 0.0327 (8) | 0.0001 (6) | −0.0001 (6) | 0.0063 (6) |
N3 | 0.0270 (8) | 0.0373 (9) | 0.0488 (10) | −0.0034 (7) | 0.0050 (7) | 0.0137 (8) |
C1 | 0.0204 (8) | 0.0294 (8) | 0.0291 (8) | −0.0001 (7) | −0.0005 (7) | 0.0012 (7) |
C2 | 0.0249 (8) | 0.0294 (9) | 0.0328 (9) | 0.0004 (7) | −0.0070 (7) | 0.0055 (7) |
C3 | 0.0292 (9) | 0.0310 (9) | 0.0289 (9) | 0.0022 (7) | −0.0036 (7) | 0.0055 (7) |
C5 | 0.0233 (9) | 0.0297 (9) | 0.0410 (10) | −0.0020 (7) | −0.0066 (8) | 0.0096 (8) |
C6 | 0.0198 (8) | 0.0334 (9) | 0.0283 (9) | −0.0018 (7) | −0.0017 (7) | 0.0026 (7) |
C7 | 0.0281 (9) | 0.0300 (9) | 0.0293 (9) | −0.0014 (7) | 0.0003 (7) | 0.0016 (7) |
C8 | 0.0224 (8) | 0.0398 (10) | 0.0458 (11) | 0.0000 (8) | −0.0026 (8) | 0.0105 (8) |
C9 | 0.0357 (10) | 0.0489 (12) | 0.0390 (11) | 0.0130 (9) | −0.0100 (9) | −0.0074 (9) |
C10 | 0.0429 (11) | 0.0425 (12) | 0.0608 (14) | −0.0079 (10) | −0.0133 (10) | 0.0226 (10) |
C4 | 0.045 (6) | 0.032 (6) | 0.051 (8) | 0.002 (4) | −0.024 (5) | −0.005 (4) |
C11 | 0.089 (9) | 0.070 (6) | 0.036 (5) | 0.016 (7) | −0.008 (6) | −0.004 (4) |
C12 | 0.077 (9) | 0.075 (10) | 0.049 (7) | −0.004 (7) | −0.023 (6) | 0.017 (6) |
C13 | 0.069 (8) | 0.075 (7) | 0.068 (9) | 0.027 (6) | −0.042 (6) | −0.025 (6) |
C4' | 0.048 (4) | 0.044 (5) | 0.037 (3) | 0.000 (3) | −0.022 (3) | −0.007 (3) |
C11' | 0.090 (6) | 0.091 (7) | 0.036 (4) | −0.025 (5) | −0.021 (4) | 0.008 (5) |
C12' | 0.079 (5) | 0.047 (4) | 0.064 (6) | −0.023 (4) | −0.035 (4) | 0.000 (3) |
C13' | 0.069 (6) | 0.093 (6) | 0.102 (8) | 0.028 (5) | −0.061 (5) | −0.039 (6) |
S1—C7 | 1.7270 (18) | C9—H9C | 0.97 |
S1—C8 | 1.7319 (18) | C10—H10A | 0.97 |
O1—N1 | 1.4116 (17) | C10—H10B | 0.97 |
O1—C2 | 1.4532 (19) | C10—H10C | 0.97 |
O2—C3 | 1.202 (2) | C4—C13 | 1.526 (9) |
O3—C3 | 1.317 (2) | C4—C12 | 1.523 (9) |
O3—C4' | 1.499 (5) | C4—C11 | 1.520 (9) |
O3—C4 | 1.501 (7) | C11—H11A | 0.97 |
O4—C5 | 1.217 (2) | C11—H11B | 0.97 |
O5—C5 | 1.256 (2) | C11—H11C | 0.97 |
O6—H6A | 0.88 (3) | C12—H12A | 0.97 |
O6—H6B | 0.81 (3) | C12—H12B | 0.97 |
N1—C1 | 1.279 (2) | C12—H12C | 0.97 |
N2—C7 | 1.327 (2) | C13—H13A | 0.97 |
N2—C6 | 1.391 (2) | C13—H13B | 0.97 |
N2—H2A | 0.90 (2) | C13—H13C | 0.97 |
N3—C7 | 1.320 (2) | C4'—C12' | 1.502 (7) |
N3—H3A | 0.89 (2) | C4'—C11' | 1.500 (7) |
N3—H3B | 0.87 (2) | C4'—C13' | 1.507 (7) |
C1—C6 | 1.462 (2) | C11'—H11D | 0.97 |
C1—C5 | 1.533 (2) | C11'—H11E | 0.97 |
C2—C9 | 1.516 (3) | C11'—H11F | 0.97 |
C2—C10 | 1.521 (3) | C12'—H12D | 0.97 |
C2—C3 | 1.532 (2) | C12'—H12E | 0.97 |
C6—C8 | 1.341 (2) | C12'—H12F | 0.97 |
C8—H8 | 0.94 | C13'—H13D | 0.97 |
C9—H9A | 0.97 | C13'—H13E | 0.97 |
C9—H9B | 0.97 | C13'—H13F | 0.97 |
C7—S1—C8 | 90.04 (8) | O3—C4—C13 | 102.1 (11) |
N1—O1—C2 | 108.93 (11) | O3—C4—C12 | 106.7 (14) |
C3—O3—C4' | 123.6 (5) | C13—C4—C12 | 109.8 (7) |
C3—O3—C4 | 118.9 (7) | O3—C4—C11 | 116.8 (16) |
H6A—O6—H6B | 107 (3) | C13—C4—C11 | 110.1 (7) |
C1—N1—O1 | 111.81 (13) | C12—C4—C11 | 110.9 (7) |
C7—N2—C6 | 114.24 (15) | C4—C11—H11A | 109.5 |
C7—N2—H2A | 118.4 (15) | C4—C11—H11B | 109.5 |
C6—N2—H2A | 127.3 (15) | H11A—C11—H11B | 109.5 |
C7—N3—H3A | 118.4 (14) | C4—C11—H11C | 109.5 |
C7—N3—H3B | 117.8 (15) | H11A—C11—H11C | 109.5 |
H3A—N3—H3B | 123 (2) | H11B—C11—H11C | 109.5 |
N1—C1—C6 | 115.08 (14) | C4—C12—H12A | 109.5 |
N1—C1—C5 | 126.26 (15) | C4—C12—H12B | 109.5 |
C6—C1—C5 | 118.66 (14) | H12A—C12—H12B | 109.5 |
O1—C2—C9 | 111.67 (14) | C4—C12—H12C | 109.5 |
O1—C2—C10 | 103.77 (13) | H12A—C12—H12C | 109.5 |
C9—C2—C10 | 111.70 (17) | H12B—C12—H12C | 109.5 |
O1—C2—C3 | 108.27 (13) | C4—C13—H13A | 109.5 |
C9—C2—C3 | 112.81 (15) | C4—C13—H13B | 109.5 |
C10—C2—C3 | 108.15 (15) | H13A—C13—H13B | 109.5 |
O2—C3—O3 | 124.96 (17) | C4—C13—H13C | 109.5 |
O2—C3—C2 | 124.58 (16) | H13A—C13—H13C | 109.5 |
O3—C3—C2 | 110.39 (15) | H13B—C13—H13C | 109.5 |
O4—C5—O5 | 127.28 (16) | O3—C4'—C12' | 111.2 (7) |
O4—C5—C1 | 116.90 (16) | O3—C4'—C11' | 104.4 (10) |
O5—C5—C1 | 115.81 (15) | C12'—C4'—C11' | 113.3 (5) |
C8—C6—N2 | 112.38 (15) | O3—C4'—C13' | 102.3 (7) |
C8—C6—C1 | 128.16 (15) | C12'—C4'—C13' | 112.0 (6) |
N2—C6—C1 | 119.32 (15) | C11'—C4'—C13' | 112.9 (5) |
N3—C7—N2 | 124.44 (17) | C4'—C11'—H11D | 109.5 |
N3—C7—S1 | 124.03 (14) | C4'—C11'—H11E | 109.5 |
N2—C7—S1 | 111.53 (12) | H11D—C11'—H11E | 109.5 |
C6—C8—S1 | 111.81 (13) | C4'—C11'—H11F | 109.5 |
C6—C8—H8 | 124.1 | H11D—C11'—H11F | 109.5 |
S1—C8—H8 | 124.1 | H11E—C11'—H11F | 109.5 |
C2—C9—H9A | 109.5 | C4'—C12'—H12D | 109.5 |
C2—C9—H9B | 109.5 | C4'—C12'—H12E | 109.5 |
H9A—C9—H9B | 109.5 | H12D—C12'—H12E | 109.5 |
C2—C9—H9C | 109.5 | C4'—C12'—H12F | 109.5 |
H9A—C9—H9C | 109.5 | H12D—C12'—H12F | 109.5 |
H9B—C9—H9C | 109.5 | H12E—C12'—H12F | 109.5 |
C2—C10—H10A | 109.5 | C4'—C13'—H13D | 109.5 |
C2—C10—H10B | 109.5 | C4'—C13'—H13E | 109.5 |
H10A—C10—H10B | 109.5 | H13D—C13'—H13E | 109.5 |
C2—C10—H10C | 109.5 | C4'—C13'—H13F | 109.5 |
H10A—C10—H10C | 109.5 | H13D—C13'—H13F | 109.5 |
H10B—C10—H10C | 109.5 | H13E—C13'—H13F | 109.5 |
C2—O1—N1—C1 | 178.74 (14) | C7—N2—C6—C8 | 0.0 (2) |
O1—N1—C1—C6 | 178.92 (13) | C7—N2—C6—C1 | −175.93 (15) |
O1—N1—C1—C5 | −1.7 (2) | N1—C1—C6—C8 | −155.94 (19) |
N1—O1—C2—C9 | −56.78 (17) | C5—C1—C6—C8 | 24.6 (3) |
N1—O1—C2—C10 | −177.25 (14) | N1—C1—C6—N2 | 19.3 (2) |
N1—O1—C2—C3 | 68.00 (16) | C5—C1—C6—N2 | −160.16 (16) |
C4'—O3—C3—O2 | −0.5 (7) | C6—N2—C7—N3 | −179.26 (17) |
C4—O3—C3—O2 | 11.0 (10) | C6—N2—C7—S1 | 0.70 (19) |
C4'—O3—C3—C2 | −177.5 (7) | C8—S1—C7—N3 | 179.04 (17) |
C4—O3—C3—C2 | −166.0 (9) | C8—S1—C7—N2 | −0.91 (14) |
O1—C2—C3—O2 | 21.9 (2) | N2—C6—C8—S1 | −0.7 (2) |
C9—C2—C3—O2 | 146.04 (18) | C1—C6—C8—S1 | 174.79 (15) |
C10—C2—C3—O2 | −89.9 (2) | C7—S1—C8—C6 | 0.92 (15) |
O1—C2—C3—O3 | −161.07 (14) | C3—O3—C4—C13 | 167.3 (10) |
C9—C2—C3—O3 | −37.0 (2) | C3—O3—C4—C12 | −77.5 (12) |
C10—C2—C3—O3 | 87.09 (18) | C3—O3—C4—C11 | 47.2 (13) |
N1—C1—C5—O4 | −100.4 (2) | C3—O3—C4'—C12' | −53.7 (12) |
C6—C1—C5—O4 | 78.9 (2) | C3—O3—C4'—C11' | 68.8 (10) |
N1—C1—C5—O5 | 79.1 (2) | C3—O3—C4'—C13' | −173.4 (9) |
C6—C1—C5—O5 | −101.53 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···O5 | 0.88 (3) | 1.85 (3) | 2.726 (2) | 179 (3) |
O6—H6B···O2 | 0.81 (3) | 1.93 (3) | 2.745 (2) | 176 (3) |
N2—H2A···O5i | 0.90 (2) | 1.81 (2) | 2.656 (2) | 156 (2) |
N3—H3A···O6ii | 0.89 (2) | 1.85 (2) | 2.736 (2) | 174 (2) |
N3—H3B···O5i | 0.87 (2) | 2.41 (2) | 3.077 (2) | 134 (2) |
N3—H3B···O1i | 0.87 (2) | 2.59 (2) | 3.360 (2) | 149 (2) |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H19N3O5S·H2O |
Mr | 347.39 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 223 |
a, b, c (Å) | 12.7918 (17), 12.2489 (15), 22.595 (3) |
V (Å3) | 3540.2 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.80 × 0.80 × 0.57 |
Data collection | |
Diffractometer | Rigaku Mercury |
Absorption correction | Multi-scan (Jacobson, 1998) |
Tmin, Tmax | 0.847, 0.888 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31871, 3232, 3096 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.091, 1.08 |
No. of reflections | 3232 |
No. of parameters | 268 |
No. of restraints | 22 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.28 |
Computer programs: CrystalClear (Rigaku, 2001), CrystalClear, CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···O5 | 0.88 (3) | 1.85 (3) | 2.726 (2) | 179 (3) |
O6—H6B···O2 | 0.81 (3) | 1.93 (3) | 2.745 (2) | 176 (3) |
N2—H2A···O5i | 0.90 (2) | 1.81 (2) | 2.656 (2) | 156 (2) |
N3—H3A···O6ii | 0.89 (2) | 1.85 (2) | 2.736 (2) | 174 (2) |
N3—H3B···O5i | 0.87 (2) | 2.41 (2) | 3.077 (2) | 134 (2) |
N3—H3B···O1i | 0.87 (2) | 2.59 (2) | 3.360 (2) | 149 (2) |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, −y+1, −z+1. |
2-Aminothiazole compounds have been extensively studied because of their biological and industrial applications (Lynch et al., 1999; Toplak et al., 2003). A search of the Cambridge Structural Database (CSD, Version 5.28 of May 2007) reveals that there are 127 crystal structures containing the 2-aminothiazole moiety. The title compound is a very important intermediate of ceftazidime, which is among the most important cephalosporin antibiotics (Powers et al., 2001). Crystal structures of some cephalosporin intermediates which contain a 2-aminothiazole group have been reported (Yoshida et al., 1989; Laurent et al., 1981). The title compound can give a reactive intermediate by reaction with diethylenetriamine-N,N,N',N'',N''- pentaacetic acid (DTPA), further, which can be used to prepare a protein-chelator conjugate (Johnson, 1999). We report here the crystal structure of the title compound.
The thiazole ring is planar to within ±0.006 (1) Å. The amino group is coplanar with the thiazole ring, with atom N3 deviating from the thiazole plane by -0.021 (2) Å. The O1/N1/C1/C2/C5/C6/C10 plane is twisted away from the thiazole plane by 21.92 (8)°. The tert-butyl group is disordered over two positions, with occupancies of 0.63 (4) and 0.37 (4). The carboxylate plane (C1/C5/O4/O5) is nearly perpendicular to the thiazole ring (dihedral angle 86.9 (1)°).
The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen bonds (Table 1) involving the O atoms of the water molecules and carboxylate groups. These hydrogen bonds link the molecules into a two-dimensional network parallel to the (001) plane (Fig. 2). The thiazole rings of the inversion-related molecules at (x, y, z) and (1 - x, 1 - y, 1 - z) are stacked with their centroids separated by a distance of 3.5387 (10) Å, indicating π-π interactions.