Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043115/at2385sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043115/at2385Isup2.hkl |
CCDC reference: 663716
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.091
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.76 From the CIF: _reflns_number_total 2710 Count of symmetry unique reflns 1421 Completeness (_total/calc) 190.71% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1289 Fraction of Friedel pairs measured 0.907 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).
An anhydrous ethanol solution (50 ml) of 5-methylthiophene-2-carbaldehyde (1.26 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of furan-2-carbohydrazide (1.26 g, 10 mmol), and the mixture was stirred at 350 K for 6 h under N2, whereupon a colourless precipitate appeared. The product was isolated, recrystallized from anhydrous ethanol and then dried in vacuo to give pure compound (I) in 81% yield. Colorless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an anhydrous ethanol solution.
The N-bound H atom and the H atoms of the water molecule were located in a difference Fourier map and refined freely. C-bound H atoms were included in calculated positions, with C—H = 0.93–0.96 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C).
In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al.,2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound (I).
In the molecular structure of the compound (I) (Fig. 1), the geometric parameters are normal. One molecules of the unit, the thiophen ring (C7–C10/S1) is approximately planar, with a maximum deviation from the mean plane of 0.0017 (3) Å for atom S1, as the furan group (C2–C5/O2) is approximately planar, with a maximum deviation from the mean plane of 0.0365 (5) Å for atom O2. The dihedral angle between these two planes is 35.20 (2)°. The crystal structure shows that the title compound includes a water molecule,which are linked via weak intermolecular N—H···O and O—H···O hydrogen bonds (Table 1), to form a zigzag packing arrangement, as illustrated in Fig.2.
For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).
C11H10N2O2S·H2O | F(000) = 528 |
Mr = 252.29 | Dx = 1.455 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2c -2n | Cell parameters from 3302 reflections |
a = 19.789 (8) Å | θ = 2.7–25.0° |
b = 4.809 (2) Å | µ = 0.28 mm−1 |
c = 12.106 (6) Å | T = 113 K |
V = 1152.1 (9) Å3 | Prism, colourless |
Z = 4 | 0.14 × 0.10 × 0.08 mm |
Rigaku Saturn diffractometer | 2710 independent reflections |
Radiation source: rotating anode | 2591 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.047 |
Detector resolution: 14.63 pixels mm-1 | θmax = 27.8°, θmin = 2.1° |
ω scans | h = −25→25 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −6→6 |
Tmin = 0.962, Tmax = 0.978 | l = −15→15 |
13209 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)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0422P)2 + 0.2449P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2710 reflections | Δρmax = 0.29 e Å−3 |
164 parameters | Δρmin = −0.31 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1289 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.10 (8) |
C11H10N2O2S·H2O | V = 1152.1 (9) Å3 |
Mr = 252.29 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 19.789 (8) Å | µ = 0.28 mm−1 |
b = 4.809 (2) Å | T = 113 K |
c = 12.106 (6) Å | 0.14 × 0.10 × 0.08 mm |
Rigaku Saturn diffractometer | 2710 independent reflections |
Absorption correction: multi-scan (Jacobson, 1998) | 2591 reflections with I > 2σ(I) |
Tmin = 0.962, Tmax = 0.978 | Rint = 0.047 |
13209 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.092 | Δρmax = 0.29 e Å−3 |
S = 1.06 | Δρmin = −0.31 e Å−3 |
2710 reflections | Absolute structure: Flack (1983), 1289 Freidel pairs |
164 parameters | Absolute structure parameter: 0.10 (8) |
1 restraint |
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 | ||
S1 | 0.32329 (3) | 0.81744 (11) | 0.57447 (5) | 0.02311 (15) | |
O1 | 0.53841 (8) | 0.1879 (3) | 0.59068 (13) | 0.0212 (4) | |
O2 | 0.54514 (7) | −0.0756 (3) | 0.86546 (13) | 0.0199 (3) | |
O3 | 0.44096 (9) | 0.3131 (4) | 0.97064 (14) | 0.0240 (4) | |
H3A | 0.4516 (13) | 0.436 (6) | 1.020 (3) | 0.036* | |
H3B | 0.4473 (15) | 0.186 (6) | 1.006 (3) | 0.036* | |
N1 | 0.48345 (10) | 0.3262 (3) | 0.74758 (16) | 0.0180 (4) | |
H1 | 0.4770 (13) | 0.299 (5) | 0.818 (2) | 0.022* | |
N2 | 0.43996 (9) | 0.5000 (4) | 0.68901 (16) | 0.0191 (4) | |
C1 | 0.52804 (11) | 0.1685 (4) | 0.69145 (18) | 0.0182 (5) | |
C2 | 0.56544 (10) | −0.0345 (4) | 0.75791 (19) | 0.0184 (4) | |
C3 | 0.61816 (11) | −0.2052 (4) | 0.7334 (2) | 0.0206 (5) | |
H3 | 0.6412 | −0.2185 | 0.6648 | 0.025* | |
C4 | 0.63178 (12) | −0.3592 (5) | 0.8308 (2) | 0.0215 (5) | |
H4 | 0.6661 | −0.4953 | 0.8401 | 0.026* | |
C5 | 0.58673 (12) | −0.2760 (5) | 0.9079 (2) | 0.0216 (5) | |
H5 | 0.5843 | −0.3466 | 0.9810 | 0.026* | |
C6 | 0.40692 (11) | 0.6696 (4) | 0.75078 (19) | 0.0187 (5) | |
H6 | 0.4172 | 0.6780 | 0.8274 | 0.022* | |
C7 | 0.35484 (12) | 0.8472 (4) | 0.70708 (18) | 0.0199 (5) | |
C8 | 0.32160 (11) | 1.0548 (5) | 0.7638 (2) | 0.0213 (5) | |
H8 | 0.3317 | 1.1048 | 0.8379 | 0.026* | |
C9 | 0.27098 (12) | 1.1854 (5) | 0.7001 (2) | 0.0229 (5) | |
H9 | 0.2434 | 1.3318 | 0.7275 | 0.027* | |
C10 | 0.26523 (11) | 1.0817 (5) | 0.5956 (2) | 0.0230 (5) | |
C11 | 0.21736 (13) | 1.1647 (5) | 0.5057 (2) | 0.0303 (6) | |
H11A | 0.1905 | 1.3246 | 0.5301 | 0.045* | |
H11B | 0.1872 | 1.0087 | 0.4888 | 0.045* | |
H11C | 0.2430 | 1.2151 | 0.4394 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0265 (3) | 0.0216 (3) | 0.0213 (3) | 0.0020 (2) | −0.0030 (2) | 0.0004 (3) |
O1 | 0.0278 (8) | 0.0208 (8) | 0.0151 (8) | 0.0021 (6) | 0.0012 (7) | 0.0005 (6) |
O2 | 0.0214 (7) | 0.0212 (8) | 0.0169 (7) | 0.0032 (6) | 0.0004 (6) | 0.0022 (7) |
O3 | 0.0340 (10) | 0.0203 (9) | 0.0176 (9) | 0.0050 (7) | −0.0002 (7) | −0.0011 (7) |
N1 | 0.0191 (10) | 0.0198 (9) | 0.0151 (9) | 0.0019 (7) | −0.0015 (7) | 0.0015 (8) |
N2 | 0.0181 (9) | 0.0172 (8) | 0.0218 (9) | 0.0017 (7) | −0.0032 (7) | 0.0035 (8) |
C1 | 0.0202 (11) | 0.0169 (10) | 0.0176 (11) | −0.0012 (8) | −0.0001 (9) | −0.0029 (8) |
C2 | 0.0208 (11) | 0.0208 (10) | 0.0136 (9) | −0.0022 (8) | −0.0003 (8) | 0.0014 (9) |
C3 | 0.0192 (11) | 0.0237 (12) | 0.0190 (11) | −0.0021 (8) | 0.0027 (9) | −0.0040 (9) |
C4 | 0.0183 (11) | 0.0218 (11) | 0.0244 (12) | 0.0024 (9) | −0.0014 (9) | 0.0010 (9) |
C5 | 0.0248 (11) | 0.0197 (11) | 0.0201 (11) | 0.0040 (9) | −0.0072 (9) | 0.0018 (9) |
C6 | 0.0187 (11) | 0.0185 (11) | 0.0188 (11) | −0.0019 (8) | −0.0002 (9) | 0.0023 (9) |
C7 | 0.0205 (12) | 0.0184 (10) | 0.0208 (12) | −0.0021 (8) | 0.0012 (9) | 0.0029 (9) |
C8 | 0.0228 (11) | 0.0217 (11) | 0.0195 (10) | −0.0004 (9) | 0.0028 (9) | 0.0010 (10) |
C9 | 0.0206 (11) | 0.0191 (11) | 0.0289 (13) | 0.0035 (8) | 0.0060 (9) | 0.0041 (10) |
C10 | 0.0179 (10) | 0.0213 (11) | 0.0297 (13) | −0.0005 (8) | 0.0002 (10) | 0.0065 (10) |
C11 | 0.0247 (13) | 0.0321 (14) | 0.0340 (14) | 0.0020 (10) | −0.0051 (11) | 0.0099 (12) |
S1—C7 | 1.728 (2) | C4—C5 | 1.351 (3) |
S1—C10 | 1.732 (2) | C4—H4 | 0.9500 |
O1—C1 | 1.241 (3) | C5—H5 | 0.9500 |
O2—C5 | 1.367 (3) | C6—C7 | 1.439 (3) |
O2—C2 | 1.377 (3) | C6—H6 | 0.9500 |
O3—H3A | 0.87 (3) | C7—C8 | 1.379 (3) |
O3—H3B | 0.76 (3) | C8—C9 | 1.411 (3) |
N1—C1 | 1.348 (3) | C8—H8 | 0.9500 |
N1—N2 | 1.393 (2) | C9—C10 | 1.365 (3) |
N1—H1 | 0.88 (3) | C9—H9 | 0.9500 |
N2—C6 | 1.285 (3) | C10—C11 | 1.497 (3) |
C1—C2 | 1.466 (3) | C11—H11A | 0.9800 |
C2—C3 | 1.360 (3) | C11—H11B | 0.9800 |
C3—C4 | 1.418 (3) | C11—H11C | 0.9800 |
C3—H3 | 0.9500 | ||
C7—S1—C10 | 92.39 (11) | N2—C6—C7 | 121.8 (2) |
C5—O2—C2 | 106.28 (17) | N2—C6—H6 | 119.1 |
H3A—O3—H3B | 97 (3) | C7—C6—H6 | 119.1 |
C1—N1—N2 | 119.04 (19) | C8—C7—C6 | 126.0 (2) |
C1—N1—H1 | 120.3 (17) | C8—C7—S1 | 110.50 (18) |
N2—N1—H1 | 119.9 (17) | C6—C7—S1 | 123.43 (17) |
C6—N2—N1 | 113.50 (19) | C7—C8—C9 | 112.9 (2) |
O1—C1—N1 | 124.2 (2) | C7—C8—H8 | 123.6 |
O1—C1—C2 | 120.4 (2) | C9—C8—H8 | 123.6 |
N1—C1—C2 | 115.4 (2) | C10—C9—C8 | 113.8 (2) |
C3—C2—O2 | 110.09 (19) | C10—C9—H9 | 123.1 |
C3—C2—C1 | 132.0 (2) | C8—C9—H9 | 123.1 |
O2—C2—C1 | 117.86 (19) | C9—C10—C11 | 129.0 (2) |
C2—C3—C4 | 106.2 (2) | C9—C10—S1 | 110.45 (17) |
C2—C3—H3 | 126.9 | C11—C10—S1 | 120.53 (19) |
C4—C3—H3 | 126.9 | C10—C11—H11A | 109.5 |
C5—C4—C3 | 107.1 (2) | C10—C11—H11B | 109.5 |
C5—C4—H4 | 126.5 | H11A—C11—H11B | 109.5 |
C3—C4—H4 | 126.5 | C10—C11—H11C | 109.5 |
C4—C5—O2 | 110.3 (2) | H11A—C11—H11C | 109.5 |
C4—C5—H5 | 124.9 | H11B—C11—H11C | 109.5 |
O2—C5—H5 | 124.9 | ||
C1—N1—N2—C6 | −170.2 (2) | C2—O2—C5—C4 | 0.1 (2) |
N2—N1—C1—O1 | 8.1 (3) | N1—N2—C6—C7 | −173.95 (18) |
N2—N1—C1—C2 | −172.18 (17) | N2—C6—C7—C8 | −172.9 (2) |
C5—O2—C2—C3 | 0.2 (2) | N2—C6—C7—S1 | 9.5 (3) |
C5—O2—C2—C1 | 178.82 (19) | C10—S1—C7—C8 | −0.37 (17) |
O1—C1—C2—C3 | 7.5 (4) | C10—S1—C7—C6 | 177.55 (19) |
N1—C1—C2—C3 | −172.2 (2) | C6—C7—C8—C9 | −177.4 (2) |
O1—C1—C2—O2 | −170.7 (2) | S1—C7—C8—C9 | 0.4 (2) |
N1—C1—C2—O2 | 9.6 (3) | C7—C8—C9—C10 | −0.3 (3) |
O2—C2—C3—C4 | −0.4 (2) | C8—C9—C10—C11 | 179.3 (2) |
C1—C2—C3—C4 | −178.8 (2) | C8—C9—C10—S1 | 0.0 (3) |
C2—C3—C4—C5 | 0.5 (3) | C7—S1—C10—C9 | 0.21 (18) |
C3—C4—C5—O2 | −0.3 (3) | C7—S1—C10—C11 | −179.17 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.88 (3) | 1.98 (3) | 2.829 (3) | 163 (2) |
O3—H3B···O1i | 0.76 (3) | 2.09 (3) | 2.843 (2) | 174 (3) |
O3—H3A···O1ii | 0.87 (3) | 2.01 (3) | 2.835 (3) | 158 (3) |
Symmetry codes: (i) −x+1, −y, z+1/2; (ii) −x+1, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H10N2O2S·H2O |
Mr | 252.29 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 113 |
a, b, c (Å) | 19.789 (8), 4.809 (2), 12.106 (6) |
V (Å3) | 1152.1 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.14 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Rigaku Saturn |
Absorption correction | Multi-scan (Jacobson, 1998) |
Tmin, Tmax | 0.962, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13209, 2710, 2591 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.655 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.092, 1.06 |
No. of reflections | 2710 |
No. of parameters | 164 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.31 |
Absolute structure | Flack (1983), 1289 Freidel pairs |
Absolute structure parameter | 0.10 (8) |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CrystalStructure (Rigaku/MSC, 2005).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.88 (3) | 1.98 (3) | 2.829 (3) | 163 (2) |
O3—H3B···O1i | 0.76 (3) | 2.09 (3) | 2.843 (2) | 174 (3) |
O3—H3A···O1ii | 0.87 (3) | 2.01 (3) | 2.835 (3) | 158 (3) |
Symmetry codes: (i) −x+1, −y, z+1/2; (ii) −x+1, −y+1, z+1/2. |
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In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al.,2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound (I).
In the molecular structure of the compound (I) (Fig. 1), the geometric parameters are normal. One molecules of the unit, the thiophen ring (C7–C10/S1) is approximately planar, with a maximum deviation from the mean plane of 0.0017 (3) Å for atom S1, as the furan group (C2–C5/O2) is approximately planar, with a maximum deviation from the mean plane of 0.0365 (5) Å for atom O2. The dihedral angle between these two planes is 35.20 (2)°. The crystal structure shows that the title compound includes a water molecule,which are linked via weak intermolecular N—H···O and O—H···O hydrogen bonds (Table 1), to form a zigzag packing arrangement, as illustrated in Fig.2.