Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041293/ci2444sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041293/ci2444Isup2.hkl |
CCDC reference: 660358
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.023
- wR factor = 0.065
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 5.36 su
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 25.01 From the CIF: _reflns_number_total 1694 Count of symmetry unique reflns 883 Completeness (_total/calc) 191.85% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 811 Fraction of Friedel pairs measured 0.918 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
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 1 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 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 thiophene-3-carbaldehyde (1.12 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 79% yield. Colourless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an anhydrous ethanol solution.
The N-bound H atom was located in a difference Fourier map and refined with a N—H distance restraint of 0.90 (1) Å. C-bound H atoms were included in calculated positions [C—H = 0.93 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(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 Schiff 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. The thiophene ring (C1–C4/S1) is planar within ±0.002 (1) Å. The furan ring (C7–C10/O2) is essentially planar, with a maximum deviation from the mean plane of 0.004 (1) Å for atom C10. The dihedral angle between these planes is 12.3 (1)°.
The molecules are linked via weak intermolecular N—H···O, C—H···S and C—H···O type hydrogen bonds (Table 1), to form a two-dimensional network parallel to the ab plane, as illustraed 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: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C10H8N2O2S | F(000) = 456 |
Mr = 220.24 | Dx = 1.505 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 3232 reflections |
a = 10.1150 (15) Å | θ = 4.0–26.2° |
b = 4.7969 (7) Å | µ = 0.31 mm−1 |
c = 20.033 (3) Å | T = 294 K |
V = 972.0 (2) Å3 | Block, colourless |
Z = 4 | 0.24 × 0.20 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 1694 independent reflections |
Radiation source: fine-focus sealed tube | 1616 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→12 |
Tmin = 0.929, Tmax = 0.946 | k = −5→4 |
4486 measured reflections | l = −23→23 |
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)] = 0.023 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.065 | w = 1/[σ2(Fo2) + (0.0391P)2 + 0.0578P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
1694 reflections | Δρmax = 0.14 e Å−3 |
140 parameters | Δρmin = −0.14 e Å−3 |
2 restraints | Absolute structure: Flack (1983), with 811 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (7) |
C10H8N2O2S | V = 972.0 (2) Å3 |
Mr = 220.24 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 10.1150 (15) Å | µ = 0.31 mm−1 |
b = 4.7969 (7) Å | T = 294 K |
c = 20.033 (3) Å | 0.24 × 0.20 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 1694 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1616 reflections with I > 2σ(I) |
Tmin = 0.929, Tmax = 0.946 | Rint = 0.018 |
4486 measured reflections |
R[F2 > 2σ(F2)] = 0.023 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.065 | Δρmax = 0.14 e Å−3 |
S = 1.11 | Δρmin = −0.14 e Å−3 |
1694 reflections | Absolute structure: Flack (1983), with 811 Friedel pairs |
140 parameters | Absolute structure parameter: 0.04 (7) |
2 restraints |
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 | 0.22029 (5) | 1.02129 (9) | 0.32352 (3) | 0.04200 (14) | |
O1 | −0.15782 (12) | 0.0679 (3) | 0.10495 (7) | 0.0473 (4) | |
O2 | −0.11967 (13) | −0.2927 (3) | 0.00357 (7) | 0.0547 (4) | |
N1 | 0.04650 (14) | 0.3353 (3) | 0.16534 (7) | 0.0352 (3) | |
N2 | 0.06307 (14) | 0.1461 (3) | 0.11429 (8) | 0.0352 (3) | |
C1 | 0.05895 (18) | 0.9185 (4) | 0.32440 (11) | 0.0412 (4) | |
H1 | −0.0038 | 0.9854 | 0.3543 | 0.049* | |
C2 | 0.03343 (17) | 0.7284 (4) | 0.27648 (10) | 0.0398 (4) | |
H2 | −0.0493 | 0.6488 | 0.2696 | 0.048* | |
C3 | 0.14683 (17) | 0.6629 (4) | 0.23753 (9) | 0.0324 (4) | |
C4 | 0.2551 (2) | 0.8089 (4) | 0.25789 (10) | 0.0383 (4) | |
H4 | 0.3382 | 0.7940 | 0.2383 | 0.046* | |
C5 | 0.1512 (2) | 0.4638 (4) | 0.18335 (9) | 0.0360 (4) | |
H5 | 0.2307 | 0.4291 | 0.1615 | 0.043* | |
C6 | −0.04417 (19) | 0.0210 (4) | 0.08752 (9) | 0.0341 (4) | |
C7 | −0.01324 (16) | −0.1763 (4) | 0.03386 (9) | 0.0348 (4) | |
C8 | 0.0966 (2) | −0.2736 (5) | 0.00599 (11) | 0.0535 (6) | |
H8 | 0.1827 | −0.2267 | 0.0177 | 0.064* | |
C9 | 0.0584 (2) | −0.4613 (5) | −0.04464 (12) | 0.0536 (6) | |
H9 | 0.1139 | −0.5610 | −0.0729 | 0.064* | |
C10 | −0.0714 (3) | −0.4667 (5) | −0.04373 (12) | 0.0538 (5) | |
H10 | −0.1232 | −0.5756 | −0.0718 | 0.065* | |
H2A | 0.1439 (12) | 0.100 (5) | 0.1005 (10) | 0.043 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0360 (2) | 0.0452 (3) | 0.0448 (2) | −0.00471 (19) | −0.0011 (2) | −0.0056 (2) |
O1 | 0.0262 (7) | 0.0623 (9) | 0.0533 (8) | 0.0012 (6) | 0.0024 (6) | −0.0137 (7) |
O2 | 0.0331 (7) | 0.0682 (10) | 0.0629 (9) | −0.0067 (6) | −0.0010 (7) | −0.0236 (8) |
N1 | 0.0298 (7) | 0.0381 (9) | 0.0378 (8) | 0.0020 (6) | −0.0006 (6) | −0.0029 (7) |
N2 | 0.0256 (7) | 0.0403 (9) | 0.0397 (8) | 0.0018 (7) | 0.0017 (6) | −0.0063 (7) |
C1 | 0.0333 (10) | 0.0482 (10) | 0.0422 (9) | 0.0001 (7) | 0.0064 (10) | 0.0007 (11) |
C2 | 0.0291 (9) | 0.0429 (10) | 0.0475 (11) | −0.0016 (8) | 0.0014 (8) | −0.0022 (9) |
C3 | 0.0268 (9) | 0.0334 (9) | 0.0372 (10) | 0.0013 (7) | 0.0002 (7) | 0.0042 (8) |
C4 | 0.0299 (9) | 0.0403 (10) | 0.0445 (10) | −0.0010 (8) | 0.0047 (7) | −0.0001 (8) |
C5 | 0.0293 (9) | 0.0382 (10) | 0.0407 (10) | 0.0023 (7) | 0.0016 (8) | 0.0021 (8) |
C6 | 0.0294 (12) | 0.0367 (10) | 0.0362 (10) | 0.0005 (7) | 0.0005 (7) | 0.0035 (7) |
C7 | 0.0309 (9) | 0.0367 (9) | 0.0367 (9) | −0.0035 (7) | −0.0036 (7) | 0.0029 (8) |
C8 | 0.0283 (10) | 0.0697 (15) | 0.0624 (13) | 0.0015 (9) | −0.0026 (9) | −0.0237 (11) |
C9 | 0.0418 (13) | 0.0604 (13) | 0.0585 (13) | 0.0018 (9) | 0.0065 (10) | −0.0197 (12) |
C10 | 0.0513 (13) | 0.0544 (12) | 0.0558 (13) | −0.0036 (10) | −0.0070 (11) | −0.0190 (11) |
S1—C4 | 1.7003 (19) | C2—H2 | 0.93 |
S1—C1 | 1.7050 (19) | C3—C4 | 1.363 (3) |
O1—C6 | 1.222 (2) | C3—C5 | 1.446 (3) |
O2—C10 | 1.354 (3) | C4—H4 | 0.93 |
O2—C7 | 1.356 (2) | C5—H5 | 0.93 |
N1—C5 | 1.277 (2) | C6—C7 | 1.466 (3) |
N1—N2 | 1.378 (2) | C7—C8 | 1.328 (3) |
N2—C6 | 1.351 (2) | C8—C9 | 1.410 (3) |
N2—H2A | 0.891 (9) | C8—H8 | 0.93 |
C1—C2 | 1.349 (3) | C9—C10 | 1.313 (3) |
C1—H1 | 0.93 | C9—H9 | 0.93 |
C2—C3 | 1.423 (2) | C10—H10 | 0.93 |
C4—S1—C1 | 91.90 (10) | N1—C5—C3 | 120.34 (18) |
C10—O2—C7 | 106.30 (16) | N1—C5—H5 | 119.8 |
C5—N1—N2 | 115.26 (15) | C3—C5—H5 | 119.8 |
C6—N2—N1 | 119.32 (15) | O1—C6—N2 | 124.07 (17) |
C6—N2—H2A | 120.3 (15) | O1—C6—C7 | 121.93 (17) |
N1—N2—H2A | 120.3 (15) | N2—C6—C7 | 113.98 (16) |
C2—C1—S1 | 111.79 (15) | C8—C7—O2 | 109.34 (17) |
C2—C1—H1 | 124.1 | C8—C7—C6 | 135.53 (17) |
S1—C1—H1 | 124.1 | O2—C7—C6 | 115.13 (15) |
C1—C2—C3 | 112.67 (17) | C7—C8—C9 | 107.30 (18) |
C1—C2—H2 | 123.7 | C7—C8—H8 | 126.3 |
C3—C2—H2 | 123.7 | C9—C8—H8 | 126.3 |
C4—C3—C2 | 111.75 (16) | C10—C9—C8 | 106.1 (2) |
C4—C3—C5 | 122.64 (18) | C10—C9—H9 | 127.0 |
C2—C3—C5 | 125.60 (17) | C8—C9—H9 | 127.0 |
C3—C4—S1 | 111.89 (15) | C9—C10—O2 | 111.0 (2) |
C3—C4—H4 | 124.1 | C9—C10—H10 | 124.5 |
S1—C4—H4 | 124.1 | O2—C10—H10 | 124.5 |
C5—N1—N2—C6 | −173.46 (17) | N1—N2—C6—C7 | −179.80 (14) |
C4—S1—C1—C2 | 0.24 (17) | C10—O2—C7—C8 | 0.4 (2) |
S1—C1—C2—C3 | −0.1 (2) | C10—O2—C7—C6 | −179.86 (17) |
C1—C2—C3—C4 | −0.1 (2) | O1—C6—C7—C8 | −177.7 (2) |
C1—C2—C3—C5 | 178.91 (18) | N2—C6—C7—C8 | 3.3 (3) |
C2—C3—C4—S1 | 0.3 (2) | O1—C6—C7—O2 | 2.6 (3) |
C5—C3—C4—S1 | −178.77 (15) | N2—C6—C7—O2 | −176.41 (15) |
C1—S1—C4—C3 | −0.29 (15) | O2—C7—C8—C9 | 0.1 (3) |
N2—N1—C5—C3 | −178.56 (15) | C6—C7—C8—C9 | −179.7 (2) |
C4—C3—C5—N1 | −178.84 (17) | C7—C8—C9—C10 | −0.5 (3) |
C2—C3—C5—N1 | 2.3 (3) | C8—C9—C10—O2 | 0.7 (3) |
N1—N2—C6—O1 | 1.2 (3) | C7—O2—C10—C9 | −0.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.89 (1) | 2.16 (1) | 3.010 (2) | 158 (2) |
C1—H1···S1ii | 0.93 | 2.86 | 3.438 (2) | 122 |
C8—H8···O1i | 0.93 | 2.50 | 3.328 (3) | 149 |
Symmetry codes: (i) x+1/2, −y, z; (ii) x−1/2, −y+2, z. |
Experimental details
Crystal data | |
Chemical formula | C10H8N2O2S |
Mr | 220.24 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 294 |
a, b, c (Å) | 10.1150 (15), 4.7969 (7), 20.033 (3) |
V (Å3) | 972.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.24 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.929, 0.946 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4486, 1694, 1616 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.023, 0.065, 1.11 |
No. of reflections | 1694 |
No. of parameters | 140 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.14 |
Absolute structure | Flack (1983), with 811 Friedel pairs |
Absolute structure parameter | 0.04 (7) |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.891 (9) | 2.163 (12) | 3.010 (2) | 158 (2) |
C1—H1···S1ii | 0.93 | 2.86 | 3.438 (2) | 122 |
C8—H8···O1i | 0.93 | 2.50 | 3.328 (3) | 149 |
Symmetry codes: (i) x+1/2, −y, z; (ii) x−1/2, −y+2, z. |
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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 Schiff 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. The thiophene ring (C1–C4/S1) is planar within ±0.002 (1) Å. The furan ring (C7–C10/O2) is essentially planar, with a maximum deviation from the mean plane of 0.004 (1) Å for atom C10. The dihedral angle between these planes is 12.3 (1)°.
The molecules are linked via weak intermolecular N—H···O, C—H···S and C—H···O type hydrogen bonds (Table 1), to form a two-dimensional network parallel to the ab plane, as illustraed in Fig.2.