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In the title compound, C11H10N2O2S·H2O, the dihedral angle between the planes of the thio­phene and furan rings is 35.20 (2)°. Mol­ecules are linked via weak inter­molecular N—H...O and O—H...O hydrogen bonds to form a zigzag packing arrangement.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043115/at2385sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043115/at2385Isup2.hkl
Contains datablock I

CCDC reference: 663716

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](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

Comment top

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.

Related literature top

For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The structure of the title molecule (I). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of (I), viwed down the a axis. Hydrogen bonds are indicated by dashed lines.
(E)—N'-[(5-Methyl-2-thienyl)methylene]furan-2-carbohydrazide monohydrate top
Crystal data top
C11H10N2O2S·H2OF(000) = 528
Mr = 252.29Dx = 1.455 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2c -2nCell parameters from 3302 reflections
a = 19.789 (8) Åθ = 2.7–25.0°
b = 4.809 (2) ŵ = 0.28 mm1
c = 12.106 (6) ÅT = 113 K
V = 1152.1 (9) Å3Prism, colourless
Z = 40.14 × 0.10 × 0.08 mm
Data collection top
Rigaku Saturn
diffractometer
2710 independent reflections
Radiation source: rotating anode2591 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.047
Detector resolution: 14.63 pixels mm-1θmax = 27.8°, θmin = 2.1°
ω scansh = 2525
Absorption correction: multi-scan
(Jacobson, 1998)
k = 66
Tmin = 0.962, Tmax = 0.978l = 1515
13209 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H 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 reflectionsΔρmax = 0.29 e Å3
164 parametersΔρmin = 0.31 e Å3
1 restraintAbsolute structure: Flack (1983), 1289 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.10 (8)
Crystal data top
C11H10N2O2S·H2OV = 1152.1 (9) Å3
Mr = 252.29Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 19.789 (8) ŵ = 0.28 mm1
b = 4.809 (2) ÅT = 113 K
c = 12.106 (6) Å0.14 × 0.10 × 0.08 mm
Data collection top
Rigaku Saturn
diffractometer
2710 independent reflections
Absorption correction: multi-scan
(Jacobson, 1998)
2591 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.978Rint = 0.047
13209 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092Δρmax = 0.29 e Å3
S = 1.06Δρmin = 0.31 e Å3
2710 reflectionsAbsolute structure: Flack (1983), 1289 Freidel pairs
164 parametersAbsolute structure parameter: 0.10 (8)
1 restraint
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.32329 (3)0.81744 (11)0.57447 (5)0.02311 (15)
O10.53841 (8)0.1879 (3)0.59068 (13)0.0212 (4)
O20.54514 (7)0.0756 (3)0.86546 (13)0.0199 (3)
O30.44096 (9)0.3131 (4)0.97064 (14)0.0240 (4)
H3A0.4516 (13)0.436 (6)1.020 (3)0.036*
H3B0.4473 (15)0.186 (6)1.006 (3)0.036*
N10.48345 (10)0.3262 (3)0.74758 (16)0.0180 (4)
H10.4770 (13)0.299 (5)0.818 (2)0.022*
N20.43996 (9)0.5000 (4)0.68901 (16)0.0191 (4)
C10.52804 (11)0.1685 (4)0.69145 (18)0.0182 (5)
C20.56544 (10)0.0345 (4)0.75791 (19)0.0184 (4)
C30.61816 (11)0.2052 (4)0.7334 (2)0.0206 (5)
H30.64120.21850.66480.025*
C40.63178 (12)0.3592 (5)0.8308 (2)0.0215 (5)
H40.66610.49530.84010.026*
C50.58673 (12)0.2760 (5)0.9079 (2)0.0216 (5)
H50.58430.34660.98100.026*
C60.40692 (11)0.6696 (4)0.75078 (19)0.0187 (5)
H60.41720.67800.82740.022*
C70.35484 (12)0.8472 (4)0.70708 (18)0.0199 (5)
C80.32160 (11)1.0548 (5)0.7638 (2)0.0213 (5)
H80.33171.10480.83790.026*
C90.27098 (12)1.1854 (5)0.7001 (2)0.0229 (5)
H90.24341.33180.72750.027*
C100.26523 (11)1.0817 (5)0.5956 (2)0.0230 (5)
C110.21736 (13)1.1647 (5)0.5057 (2)0.0303 (6)
H11A0.19051.32460.53010.045*
H11B0.18721.00870.48880.045*
H11C0.24301.21510.43940.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0265 (3)0.0216 (3)0.0213 (3)0.0020 (2)0.0030 (2)0.0004 (3)
O10.0278 (8)0.0208 (8)0.0151 (8)0.0021 (6)0.0012 (7)0.0005 (6)
O20.0214 (7)0.0212 (8)0.0169 (7)0.0032 (6)0.0004 (6)0.0022 (7)
O30.0340 (10)0.0203 (9)0.0176 (9)0.0050 (7)0.0002 (7)0.0011 (7)
N10.0191 (10)0.0198 (9)0.0151 (9)0.0019 (7)0.0015 (7)0.0015 (8)
N20.0181 (9)0.0172 (8)0.0218 (9)0.0017 (7)0.0032 (7)0.0035 (8)
C10.0202 (11)0.0169 (10)0.0176 (11)0.0012 (8)0.0001 (9)0.0029 (8)
C20.0208 (11)0.0208 (10)0.0136 (9)0.0022 (8)0.0003 (8)0.0014 (9)
C30.0192 (11)0.0237 (12)0.0190 (11)0.0021 (8)0.0027 (9)0.0040 (9)
C40.0183 (11)0.0218 (11)0.0244 (12)0.0024 (9)0.0014 (9)0.0010 (9)
C50.0248 (11)0.0197 (11)0.0201 (11)0.0040 (9)0.0072 (9)0.0018 (9)
C60.0187 (11)0.0185 (11)0.0188 (11)0.0019 (8)0.0002 (9)0.0023 (9)
C70.0205 (12)0.0184 (10)0.0208 (12)0.0021 (8)0.0012 (9)0.0029 (9)
C80.0228 (11)0.0217 (11)0.0195 (10)0.0004 (9)0.0028 (9)0.0010 (10)
C90.0206 (11)0.0191 (11)0.0289 (13)0.0035 (8)0.0060 (9)0.0041 (10)
C100.0179 (10)0.0213 (11)0.0297 (13)0.0005 (8)0.0002 (10)0.0065 (10)
C110.0247 (13)0.0321 (14)0.0340 (14)0.0020 (10)0.0051 (11)0.0099 (12)
Geometric parameters (Å, º) top
S1—C71.728 (2)C4—C51.351 (3)
S1—C101.732 (2)C4—H40.9500
O1—C11.241 (3)C5—H50.9500
O2—C51.367 (3)C6—C71.439 (3)
O2—C21.377 (3)C6—H60.9500
O3—H3A0.87 (3)C7—C81.379 (3)
O3—H3B0.76 (3)C8—C91.411 (3)
N1—C11.348 (3)C8—H80.9500
N1—N21.393 (2)C9—C101.365 (3)
N1—H10.88 (3)C9—H90.9500
N2—C61.285 (3)C10—C111.497 (3)
C1—C21.466 (3)C11—H11A0.9800
C2—C31.360 (3)C11—H11B0.9800
C3—C41.418 (3)C11—H11C0.9800
C3—H30.9500
C7—S1—C1092.39 (11)N2—C6—C7121.8 (2)
C5—O2—C2106.28 (17)N2—C6—H6119.1
H3A—O3—H3B97 (3)C7—C6—H6119.1
C1—N1—N2119.04 (19)C8—C7—C6126.0 (2)
C1—N1—H1120.3 (17)C8—C7—S1110.50 (18)
N2—N1—H1119.9 (17)C6—C7—S1123.43 (17)
C6—N2—N1113.50 (19)C7—C8—C9112.9 (2)
O1—C1—N1124.2 (2)C7—C8—H8123.6
O1—C1—C2120.4 (2)C9—C8—H8123.6
N1—C1—C2115.4 (2)C10—C9—C8113.8 (2)
C3—C2—O2110.09 (19)C10—C9—H9123.1
C3—C2—C1132.0 (2)C8—C9—H9123.1
O2—C2—C1117.86 (19)C9—C10—C11129.0 (2)
C2—C3—C4106.2 (2)C9—C10—S1110.45 (17)
C2—C3—H3126.9C11—C10—S1120.53 (19)
C4—C3—H3126.9C10—C11—H11A109.5
C5—C4—C3107.1 (2)C10—C11—H11B109.5
C5—C4—H4126.5H11A—C11—H11B109.5
C3—C4—H4126.5C10—C11—H11C109.5
C4—C5—O2110.3 (2)H11A—C11—H11C109.5
C4—C5—H5124.9H11B—C11—H11C109.5
O2—C5—H5124.9
C1—N1—N2—C6170.2 (2)C2—O2—C5—C40.1 (2)
N2—N1—C1—O18.1 (3)N1—N2—C6—C7173.95 (18)
N2—N1—C1—C2172.18 (17)N2—C6—C7—C8172.9 (2)
C5—O2—C2—C30.2 (2)N2—C6—C7—S19.5 (3)
C5—O2—C2—C1178.82 (19)C10—S1—C7—C80.37 (17)
O1—C1—C2—C37.5 (4)C10—S1—C7—C6177.55 (19)
N1—C1—C2—C3172.2 (2)C6—C7—C8—C9177.4 (2)
O1—C1—C2—O2170.7 (2)S1—C7—C8—C90.4 (2)
N1—C1—C2—O29.6 (3)C7—C8—C9—C100.3 (3)
O2—C2—C3—C40.4 (2)C8—C9—C10—C11179.3 (2)
C1—C2—C3—C4178.8 (2)C8—C9—C10—S10.0 (3)
C2—C3—C4—C50.5 (3)C7—S1—C10—C90.21 (18)
C3—C4—C5—O20.3 (3)C7—S1—C10—C11179.17 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.88 (3)1.98 (3)2.829 (3)163 (2)
O3—H3B···O1i0.76 (3)2.09 (3)2.843 (2)174 (3)
O3—H3A···O1ii0.87 (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 formulaC11H10N2O2S·H2O
Mr252.29
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)113
a, b, c (Å)19.789 (8), 4.809 (2), 12.106 (6)
V3)1152.1 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.14 × 0.10 × 0.08
Data collection
DiffractometerRigaku Saturn
Absorption correctionMulti-scan
(Jacobson, 1998)
Tmin, Tmax0.962, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections
13209, 2710, 2591
Rint0.047
(sin θ/λ)max1)0.655
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.092, 1.06
No. of reflections2710
No. of parameters164
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.31
Absolute structureFlack (1983), 1289 Freidel pairs
Absolute structure parameter0.10 (8)

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.88 (3)1.98 (3)2.829 (3)163 (2)
O3—H3B···O1i0.76 (3)2.09 (3)2.843 (2)174 (3)
O3—H3A···O1ii0.87 (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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