Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052798/hk2351sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052798/hk2351Isup2.hkl |
CCDC reference: 667470
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.007 Å
- R factor = 0.060
- wR factor = 0.173
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT432_ALERT_2_C Short Inter X...Y Contact C9 .. C9 .. 3.15 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 48
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see: Barreca et al. (2002); Botti et al. (1996). For a related structure, see: Guo et al. (2006). For bond-length data, see: Allen et al. (1987).
Thiazolidine-2,4-dione (10 mmol) and 2-fluorobenzaldehyde (10 mmol) were dissolved in ethanol (10 ml) in a round-bottomed flask (50 ml) and 5 drops of piperidine were added. The flask was heated in a modified domestic microwave oven at 300 W for 5 min. After cooling, the mixture was poured into water, the crude compound filtered out, and recrystallized from ethanol. Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.
H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).
Thiazolidines are an important class of heteroaromatic compounds and have widespread applications from pharmaceuticals (Barreca et al., 2002) to materials (Botti et al., 1996). As part of our studies in this area (Guo et al., 2006), we report herein the synthesis and crystal structure of the title compound, (I).
In the molecule of (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The intramolecular C—H···O, C—H···F and C—H···S hydrogen bonds (Table 1) result in the formation of the nearly planar five-membered rings; C (F/C3/C4/C7/H7A) and D (O1/C7–C9/H7A), and one non-planar six-membered ring E (S/C4/C5/C7/C8/H5A), the five-membered rings being also nearly co-planar with the adjacent rings A (C1–C6) and B (S/N/C8–C10). The dihedral angles between them are A/C = 2.08 (2)° and B/D = 1.18 (3)°. The planar rings A (C1–C6) and B (S/N/C8–C10) are oriented at a dihedral angle of 8.90 (3)°.
In the crystal structure, intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) link the molecules, in which they seem to be effective in the stabilization of the structure.
For general background, see: Barreca et al. (2002); Botti et al. (1996). For a related structure, see: Guo et al. (2006). For bond-length data, see: Allen et al. (1987).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).
Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines. |
C10H6FNO2S | F(000) = 456 |
Mr = 223.22 | Dx = 1.570 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 5.120 (1) Å | θ = 9–13° |
b = 21.189 (4) Å | µ = 0.33 mm−1 |
c = 9.0310 (18) Å | T = 294 K |
β = 105.49 (3)° | Block, colourless |
V = 944.2 (3) Å3 | 0.40 × 0.10 × 0.10 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1283 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.043 |
Graphite monochromator | θmax = 25.9°, θmin = 1.9° |
ω/2θ scans | h = −6→6 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→26 |
Tmin = 0.878, Tmax = 0.967 | l = 0→11 |
2060 measured reflections | 3 standard reflections every 120 min |
1853 independent reflections | intensity decay: none |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.05P)2 + 3P] where P = (Fo2 + 2Fc2)/3 |
1853 reflections | (Δ/σ)max < 0.001 |
136 parameters | Δρmax = 0.38 e Å−3 |
48 restraints | Δρmin = −0.47 e Å−3 |
C10H6FNO2S | V = 944.2 (3) Å3 |
Mr = 223.22 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.120 (1) Å | µ = 0.33 mm−1 |
b = 21.189 (4) Å | T = 294 K |
c = 9.0310 (18) Å | 0.40 × 0.10 × 0.10 mm |
β = 105.49 (3)° |
Enraf–Nonius CAD-4 diffractometer | 1283 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.043 |
Tmin = 0.878, Tmax = 0.967 | 3 standard reflections every 120 min |
2060 measured reflections | intensity decay: none |
1853 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | 48 restraints |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.38 e Å−3 |
1853 reflections | Δρmin = −0.47 e Å−3 |
136 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 | ||
S | 0.4369 (2) | 0.65416 (5) | 0.48345 (13) | 0.0472 (3) | |
N | 0.7813 (7) | 0.57028 (17) | 0.4442 (4) | 0.0435 (9) | |
H0A | 0.8957 | 0.5506 | 0.4065 | 0.052* | |
F | 0.2877 (8) | 0.53827 (18) | 0.9920 (4) | 0.0975 (13) | |
O1 | 0.8214 (7) | 0.50293 (14) | 0.6463 (4) | 0.0489 (8) | |
C1 | −0.0740 (10) | 0.6837 (3) | 0.9594 (6) | 0.0605 (13) | |
H1A | −0.1900 | 0.7048 | 1.0060 | 0.073* | |
O2 | 0.6738 (7) | 0.64701 (16) | 0.2582 (4) | 0.0585 (9) | |
C2 | 0.0270 (10) | 0.6253 (3) | 1.0131 (5) | 0.0589 (13) | |
H2A | −0.0176 | 0.6068 | 1.0965 | 0.071* | |
C3 | 0.1953 (10) | 0.5952 (2) | 0.9402 (5) | 0.0527 (12) | |
C4 | 0.2695 (8) | 0.6197 (2) | 0.8152 (5) | 0.0389 (9) | |
C5 | 0.1655 (10) | 0.6795 (2) | 0.7646 (5) | 0.0520 (11) | |
H5A | 0.2109 | 0.6984 | 0.6819 | 0.062* | |
C6 | −0.0040 (11) | 0.7108 (2) | 0.8368 (6) | 0.0591 (13) | |
H6A | −0.0711 | 0.7504 | 0.8021 | 0.071* | |
C7 | 0.4484 (8) | 0.5833 (2) | 0.7487 (5) | 0.0408 (10) | |
H7A | 0.5179 | 0.5470 | 0.8029 | 0.049* | |
C8 | 0.5305 (8) | 0.5934 (2) | 0.6216 (5) | 0.0400 (9) | |
C9 | 0.7224 (8) | 0.55010 (19) | 0.5755 (5) | 0.0374 (9) | |
C10 | 0.6489 (9) | 0.6235 (2) | 0.3753 (5) | 0.0462 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0537 (7) | 0.0454 (6) | 0.0477 (6) | 0.0082 (5) | 0.0226 (5) | 0.0061 (5) |
N | 0.048 (2) | 0.046 (2) | 0.046 (2) | 0.0069 (16) | 0.0288 (17) | 0.0035 (16) |
F | 0.124 (3) | 0.101 (3) | 0.094 (3) | 0.053 (2) | 0.075 (2) | 0.051 (2) |
O1 | 0.061 (2) | 0.0406 (16) | 0.0552 (19) | 0.0089 (14) | 0.0323 (16) | 0.0024 (14) |
C1 | 0.054 (3) | 0.074 (3) | 0.057 (3) | 0.011 (2) | 0.022 (2) | −0.020 (2) |
O2 | 0.073 (2) | 0.062 (2) | 0.0510 (19) | 0.0049 (18) | 0.0348 (17) | 0.0121 (16) |
C2 | 0.055 (3) | 0.085 (3) | 0.045 (2) | 0.008 (3) | 0.027 (2) | −0.003 (2) |
C3 | 0.062 (3) | 0.063 (3) | 0.041 (2) | 0.012 (2) | 0.027 (2) | 0.007 (2) |
C4 | 0.037 (2) | 0.047 (2) | 0.037 (2) | 0.0007 (18) | 0.0169 (17) | −0.0062 (17) |
C5 | 0.064 (3) | 0.047 (2) | 0.052 (3) | 0.009 (2) | 0.027 (2) | 0.000 (2) |
C6 | 0.070 (3) | 0.049 (3) | 0.066 (3) | 0.008 (2) | 0.031 (3) | −0.010 (2) |
C7 | 0.044 (2) | 0.039 (2) | 0.042 (2) | 0.0083 (18) | 0.0166 (19) | 0.0022 (18) |
C8 | 0.042 (2) | 0.042 (2) | 0.040 (2) | −0.0025 (18) | 0.0171 (18) | −0.0029 (18) |
C9 | 0.039 (2) | 0.038 (2) | 0.040 (2) | −0.0034 (18) | 0.0188 (18) | −0.0008 (18) |
C10 | 0.044 (2) | 0.054 (3) | 0.042 (2) | −0.001 (2) | 0.0143 (19) | 0.000 (2) |
S—C10 | 1.767 (5) | C2—C3 | 1.374 (6) |
S—C8 | 1.767 (4) | C2—H2A | 0.9300 |
N—C9 | 1.368 (5) | C3—C4 | 1.385 (6) |
N—C10 | 1.376 (6) | C4—C5 | 1.403 (6) |
N—H0A | 0.8600 | C4—C7 | 1.444 (5) |
F—C3 | 1.333 (6) | C5—C6 | 1.385 (6) |
O1—C9 | 1.221 (5) | C5—H5A | 0.9300 |
C1—C6 | 1.377 (7) | C6—H6A | 0.9300 |
C1—C2 | 1.378 (7) | C7—C8 | 1.341 (6) |
C1—H1A | 0.9300 | C7—H7A | 0.9300 |
O2—C10 | 1.206 (5) | C8—C9 | 1.483 (6) |
C10—S—C8 | 91.8 (2) | C6—C5—H5A | 119.7 |
C9—N—C10 | 116.9 (3) | C4—C5—H5A | 119.7 |
C9—N—H0A | 121.6 | C1—C6—C5 | 120.6 (5) |
C10—N—H0A | 121.6 | C1—C6—H6A | 119.7 |
C6—C1—C2 | 120.2 (4) | C5—C6—H6A | 119.7 |
C6—C1—H1A | 119.9 | C8—C7—C4 | 130.5 (4) |
C2—C1—H1A | 119.9 | C8—C7—H7A | 114.8 |
C3—C2—C1 | 118.2 (5) | C4—C7—H7A | 114.8 |
C3—C2—H2A | 120.9 | C7—C8—C9 | 121.6 (4) |
C1—C2—H2A | 120.9 | C7—C8—S | 129.2 (3) |
F—C3—C2 | 117.5 (4) | C9—C8—S | 109.2 (3) |
F—C3—C4 | 118.4 (4) | O1—C9—N | 123.6 (4) |
C2—C3—C4 | 124.0 (5) | O1—C9—C8 | 125.0 (4) |
C3—C4—C5 | 116.2 (4) | N—C9—C8 | 111.4 (4) |
C3—C4—C7 | 118.7 (4) | O2—C10—N | 125.5 (4) |
C5—C4—C7 | 125.1 (4) | O2—C10—S | 123.9 (4) |
C6—C5—C4 | 120.7 (4) | N—C10—S | 110.6 (3) |
C6—C1—C2—C3 | −0.7 (8) | C4—C7—C8—S | −2.9 (8) |
C1—C2—C3—F | −178.9 (5) | C10—S—C8—C7 | −179.8 (4) |
C1—C2—C3—C4 | −0.3 (8) | C10—S—C8—C9 | −1.2 (3) |
F—C3—C4—C5 | 179.6 (5) | C10—N—C9—O1 | 178.5 (4) |
C2—C3—C4—C5 | 1.0 (7) | C10—N—C9—C8 | −2.9 (5) |
F—C3—C4—C7 | −1.5 (7) | C7—C8—C9—O1 | −0.3 (7) |
C2—C3—C4—C7 | 179.9 (5) | S—C8—C9—O1 | −179.0 (4) |
C3—C4—C5—C6 | −0.8 (7) | C7—C8—C9—N | −178.8 (4) |
C7—C4—C5—C6 | −179.6 (4) | S—C8—C9—N | 2.4 (4) |
C2—C1—C6—C5 | 0.9 (8) | C9—N—C10—O2 | −178.8 (4) |
C4—C5—C6—C1 | −0.1 (8) | C9—N—C10—S | 1.9 (5) |
C3—C4—C7—C8 | 173.4 (5) | C8—S—C10—O2 | −179.6 (4) |
C5—C4—C7—C8 | −7.8 (8) | C8—S—C10—N | −0.3 (3) |
C4—C7—C8—C9 | 178.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N—H0A···O1i | 0.86 | 2.00 | 2.846 (5) | 170 |
C2—H2A···O2ii | 0.93 | 2.57 | 3.243 (6) | 130 |
C5—H5A···S | 0.93 | 2.56 | 3.248 (5) | 131 |
C6—H6A···O2iii | 0.93 | 2.51 | 3.417 (6) | 165 |
C7—H7A···F | 0.93 | 2.33 | 2.717 (6) | 105 |
C7—H7A···O1 | 0.93 | 2.54 | 2.889 (6) | 102 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1, y, z+1; (iii) x−1, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H6FNO2S |
Mr | 223.22 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 5.120 (1), 21.189 (4), 9.0310 (18) |
β (°) | 105.49 (3) |
V (Å3) | 944.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.40 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.878, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2060, 1853, 1283 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.615 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.173, 1.00 |
No. of reflections | 1853 |
No. of parameters | 136 |
No. of restraints | 48 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.47 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
N—H0A···O1i | 0.86 | 2.00 | 2.846 (5) | 170.00 |
C2—H2A···O2ii | 0.93 | 2.57 | 3.243 (6) | 130.00 |
C5—H5A···S | 0.93 | 2.56 | 3.248 (5) | 131.00 |
C6—H6A···O2iii | 0.93 | 2.51 | 3.417 (6) | 165.00 |
C7—H7A···F | 0.93 | 2.33 | 2.717 (6) | 105.00 |
C7—H7A···O1 | 0.93 | 2.54 | 2.889 (6) | 102.00 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1, y, z+1; (iii) x−1, −y+3/2, z+1/2. |
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Thiazolidines are an important class of heteroaromatic compounds and have widespread applications from pharmaceuticals (Barreca et al., 2002) to materials (Botti et al., 1996). As part of our studies in this area (Guo et al., 2006), we report herein the synthesis and crystal structure of the title compound, (I).
In the molecule of (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The intramolecular C—H···O, C—H···F and C—H···S hydrogen bonds (Table 1) result in the formation of the nearly planar five-membered rings; C (F/C3/C4/C7/H7A) and D (O1/C7–C9/H7A), and one non-planar six-membered ring E (S/C4/C5/C7/C8/H5A), the five-membered rings being also nearly co-planar with the adjacent rings A (C1–C6) and B (S/N/C8–C10). The dihedral angles between them are A/C = 2.08 (2)° and B/D = 1.18 (3)°. The planar rings A (C1–C6) and B (S/N/C8–C10) are oriented at a dihedral angle of 8.90 (3)°.
In the crystal structure, intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) link the molecules, in which they seem to be effective in the stabilization of the structure.