Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041323/ci2448sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041323/ci2448Isup2.hkl |
CCDC reference: 660359
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.051
- wR factor = 0.126
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 0 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-methylfuran-2-carbaldehyde (1.10 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, yielding a colourless precipitate. The product was isolated, recrystallized from anhydrous ethanol and then dried in vacuo to give pure compound (I) in 92% yield. Colourless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an anhydrous ethanol solution.
H atoms were included in calculated positions [N—H = 0.86 Å, C—H = 0.93 (aromatic) or 0.96 Å (methyl)] and refined using a riding model, with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(C) for methyl H atoms.
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 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 O1/C2—C5 furan ring is planar, with an r.m.s. deviation for the fitted atoms of 0.004 Å, as is the furan ring O3/C8—C11, with an r.m.s. deviation of 0.003 Å. The dihedral angle between these two planes is 4.2 (2)°. The O2/C7/N2/N1/C6 plane (r.m.s. deviation 0.035 Å) forms dihedral angles of 3.1 (1)° and 5.1 (1)°, respectively, with the O1/C2—C5 and O3/C8—C11 furan rings.
Intermolecular N—H···O hydrogen bonds link the molecules into chains running along the b axis. These chains are cross-linked via C—H···O hydrogen bonds (Table 1) forming a two-dimensional network structure, as illustrated in Fig. 2. In addition, π-π stacking interactions involving the inversion-related O3/C8—C11 furan rings, with a centroid-to-centroid distance of 3.4866 (14) Å is observed.
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).
C11H10N2O3 | F(000) = 912 |
Mr = 218.21 | Dx = 1.323 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 8064 reflections |
a = 11.402 (2) Å | θ = 1.8–27.4° |
b = 7.9941 (16) Å | µ = 0.10 mm−1 |
c = 24.039 (5) Å | T = 293 K |
V = 2191.1 (7) Å3 | Block, colourless |
Z = 8 | 0.14 × 0.10 × 0.06 mm |
Rigaku Saturn diffractometer | 1931 independent reflections |
Radiation source: rotating anode | 1673 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.044 |
ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.986, Tmax = 0.994 | k = −9→8 |
12318 measured reflections | l = −28→26 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0628P)2 + 0.3175P] where P = (Fo2 + 2Fc2)/3 |
1931 reflections | (Δ/σ)max = 0.001 |
146 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C11H10N2O3 | V = 2191.1 (7) Å3 |
Mr = 218.21 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 11.402 (2) Å | µ = 0.10 mm−1 |
b = 7.9941 (16) Å | T = 293 K |
c = 24.039 (5) Å | 0.14 × 0.10 × 0.06 mm |
Rigaku Saturn diffractometer | 1931 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1673 reflections with I > 2σ(I) |
Tmin = 0.986, Tmax = 0.994 | Rint = 0.044 |
12318 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.12 e Å−3 |
1931 reflections | Δρmin = −0.19 e Å−3 |
146 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 | ||
O1 | 0.82709 (12) | 0.11965 (16) | 0.75358 (5) | 0.0600 (4) | |
O2 | 0.61482 (11) | 0.07779 (15) | 0.57388 (5) | 0.0553 (4) | |
O3 | 0.67924 (12) | 0.45165 (16) | 0.49989 (5) | 0.0633 (4) | |
N1 | 0.75995 (13) | 0.22824 (19) | 0.64816 (5) | 0.0504 (4) | |
N2 | 0.73032 (13) | 0.29844 (18) | 0.59727 (5) | 0.0506 (4) | |
H2 | 0.7579 | 0.3945 | 0.5878 | 0.061* | |
C1 | 0.8569 (2) | −0.0544 (4) | 0.83485 (10) | 0.1005 (9) | |
H1A | 0.9007 | −0.0553 | 0.8690 | 0.151* | |
H1B | 0.8811 | −0.1468 | 0.8120 | 0.151* | |
H1C | 0.7748 | −0.0642 | 0.8429 | 0.151* | |
C2 | 0.87878 (18) | 0.1036 (3) | 0.80507 (8) | 0.0669 (6) | |
C3 | 0.9411 (2) | 0.2403 (3) | 0.81651 (9) | 0.0780 (7) | |
H3 | 0.9849 | 0.2594 | 0.8485 | 0.094* | |
C4 | 0.9284 (2) | 0.3510 (3) | 0.77109 (9) | 0.0749 (6) | |
H4 | 0.9612 | 0.4570 | 0.7677 | 0.090* | |
C5 | 0.85954 (16) | 0.2732 (2) | 0.73358 (7) | 0.0550 (5) | |
C6 | 0.81970 (16) | 0.3244 (2) | 0.67981 (7) | 0.0532 (5) | |
H6 | 0.8379 | 0.4315 | 0.6674 | 0.064* | |
C7 | 0.65803 (15) | 0.2147 (2) | 0.56285 (7) | 0.0450 (4) | |
C8 | 0.63024 (15) | 0.2980 (2) | 0.51031 (7) | 0.0480 (4) | |
C9 | 0.55807 (19) | 0.2560 (3) | 0.46885 (7) | 0.0618 (5) | |
H9 | 0.5140 | 0.1585 | 0.4662 | 0.074* | |
C10 | 0.5615 (2) | 0.3884 (3) | 0.42979 (8) | 0.0738 (6) | |
H10 | 0.5208 | 0.3943 | 0.3963 | 0.089* | |
C11 | 0.6341 (2) | 0.5024 (3) | 0.45028 (8) | 0.0730 (6) | |
H11 | 0.6519 | 0.6034 | 0.4330 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0632 (8) | 0.0663 (9) | 0.0505 (8) | 0.0005 (6) | −0.0081 (6) | 0.0187 (6) |
O2 | 0.0660 (8) | 0.0460 (7) | 0.0538 (8) | −0.0036 (6) | 0.0003 (6) | 0.0027 (5) |
O3 | 0.0770 (9) | 0.0610 (9) | 0.0520 (8) | −0.0064 (7) | −0.0096 (6) | 0.0144 (6) |
N1 | 0.0594 (9) | 0.0488 (9) | 0.0431 (8) | 0.0021 (7) | −0.0040 (7) | 0.0120 (7) |
N2 | 0.0634 (9) | 0.0434 (8) | 0.0449 (8) | −0.0035 (7) | −0.0054 (7) | 0.0119 (6) |
C1 | 0.0980 (18) | 0.125 (2) | 0.0788 (16) | 0.0043 (16) | −0.0065 (14) | 0.0576 (16) |
C2 | 0.0590 (12) | 0.0928 (16) | 0.0490 (11) | 0.0119 (11) | −0.0041 (9) | 0.0228 (11) |
C3 | 0.0727 (14) | 0.112 (2) | 0.0490 (12) | 0.0048 (14) | −0.0152 (10) | 0.0068 (12) |
C4 | 0.0829 (15) | 0.0836 (16) | 0.0583 (13) | −0.0145 (12) | −0.0127 (11) | 0.0051 (11) |
C5 | 0.0606 (11) | 0.0566 (11) | 0.0479 (10) | −0.0004 (9) | −0.0040 (9) | 0.0099 (8) |
C6 | 0.0633 (11) | 0.0492 (11) | 0.0472 (10) | −0.0014 (9) | −0.0032 (9) | 0.0069 (8) |
C7 | 0.0503 (9) | 0.0429 (10) | 0.0420 (9) | 0.0062 (8) | 0.0050 (7) | 0.0011 (7) |
C8 | 0.0575 (10) | 0.0445 (10) | 0.0422 (9) | 0.0057 (8) | 0.0025 (8) | 0.0008 (7) |
C9 | 0.0807 (13) | 0.0561 (12) | 0.0487 (11) | 0.0034 (10) | −0.0073 (10) | −0.0061 (8) |
C10 | 0.1039 (17) | 0.0730 (14) | 0.0445 (11) | 0.0125 (13) | −0.0174 (11) | −0.0015 (10) |
C11 | 0.1045 (18) | 0.0669 (14) | 0.0477 (11) | 0.0048 (13) | −0.0100 (11) | 0.0181 (10) |
O1—C5 | 1.369 (2) | C3—C4 | 1.413 (3) |
O1—C2 | 1.377 (2) | C3—H3 | 0.93 |
O2—C7 | 1.229 (2) | C4—C5 | 1.347 (3) |
O3—C11 | 1.361 (2) | C4—H4 | 0.93 |
O3—C8 | 1.372 (2) | C5—C6 | 1.430 (2) |
N1—C6 | 1.278 (2) | C6—H6 | 0.93 |
N1—N2 | 1.3876 (18) | C7—C8 | 1.463 (2) |
N2—C7 | 1.346 (2) | C8—C9 | 1.335 (2) |
N2—H2 | 0.86 | C9—C10 | 1.415 (3) |
C1—C2 | 1.473 (3) | C9—H9 | 0.93 |
C1—H1A | 0.96 | C10—C11 | 1.326 (3) |
C1—H1B | 0.96 | C10—H10 | 0.93 |
C1—H1C | 0.96 | C11—H11 | 0.93 |
C2—C3 | 1.332 (3) | ||
C5—O1—C2 | 106.47 (16) | C4—C5—O1 | 109.64 (17) |
C11—O3—C8 | 105.83 (15) | C4—C5—C6 | 131.16 (19) |
C6—N1—N2 | 114.29 (15) | O1—C5—C6 | 119.21 (16) |
C7—N2—N1 | 119.33 (15) | N1—C6—C5 | 122.38 (17) |
C7—N2—H2 | 120.3 | N1—C6—H6 | 118.8 |
N1—N2—H2 | 120.3 | C5—C6—H6 | 118.8 |
C2—C1—H1A | 109.5 | O2—C7—N2 | 123.75 (15) |
C2—C1—H1B | 109.5 | O2—C7—C8 | 120.33 (16) |
H1A—C1—H1B | 109.5 | N2—C7—C8 | 115.91 (16) |
C2—C1—H1C | 109.5 | C9—C8—O3 | 109.85 (16) |
H1A—C1—H1C | 109.5 | C9—C8—C7 | 131.57 (18) |
H1B—C1—H1C | 109.5 | O3—C8—C7 | 118.48 (15) |
C3—C2—O1 | 109.71 (18) | C8—C9—C10 | 106.88 (19) |
C3—C2—C1 | 133.9 (2) | C8—C9—H9 | 126.6 |
O1—C2—C1 | 116.4 (2) | C10—C9—H9 | 126.6 |
C2—C3—C4 | 107.44 (19) | C11—C10—C9 | 106.52 (18) |
C2—C3—H3 | 126.3 | C11—C10—H10 | 126.7 |
C4—C3—H3 | 126.3 | C9—C10—H10 | 126.7 |
C5—C4—C3 | 106.7 (2) | C10—C11—O3 | 110.90 (19) |
C5—C4—H4 | 126.6 | C10—C11—H11 | 124.5 |
C3—C4—H4 | 126.6 | O3—C11—H11 | 124.5 |
C6—N1—N2—C7 | −173.65 (15) | N1—N2—C7—O2 | 0.6 (3) |
C5—O1—C2—C3 | −0.3 (2) | N1—N2—C7—C8 | 179.41 (14) |
C5—O1—C2—C1 | −179.49 (19) | C11—O3—C8—C9 | 0.0 (2) |
O1—C2—C3—C4 | 0.8 (3) | C11—O3—C8—C7 | −176.96 (16) |
C1—C2—C3—C4 | 179.8 (3) | O2—C7—C8—C9 | 3.0 (3) |
C2—C3—C4—C5 | −1.0 (3) | N2—C7—C8—C9 | −175.80 (18) |
C3—C4—C5—O1 | 0.8 (3) | O2—C7—C8—O3 | 179.23 (15) |
C3—C4—C5—C6 | −178.7 (2) | N2—C7—C8—O3 | 0.4 (2) |
C2—O1—C5—C4 | −0.3 (2) | O3—C8—C9—C10 | 0.4 (2) |
C2—O1—C5—C6 | 179.21 (17) | C7—C8—C9—C10 | 176.85 (19) |
N2—N1—C6—C5 | −179.21 (16) | C8—C9—C10—C11 | −0.7 (3) |
C4—C5—C6—N1 | 175.4 (2) | C9—C10—C11—O3 | 0.7 (3) |
O1—C5—C6—N1 | −4.0 (3) | C8—O3—C11—C10 | −0.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.09 | 2.902 (2) | 157 |
C9—H9···O2ii | 0.93 | 2.58 | 3.473 (3) | 161 |
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C11H10N2O3 |
Mr | 218.21 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 11.402 (2), 7.9941 (16), 24.039 (5) |
V (Å3) | 2191.1 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.14 × 0.10 × 0.06 |
Data collection | |
Diffractometer | Rigaku Saturn |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.986, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12318, 1931, 1673 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.126, 1.12 |
No. of reflections | 1931 |
No. of parameters | 146 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.19 |
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 |
N2—H2···O2i | 0.86 | 2.09 | 2.902 (2) | 157 |
C9—H9···O2ii | 0.93 | 2.58 | 3.473 (3) | 161 |
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+1, −y, −z+1. |
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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 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 O1/C2—C5 furan ring is planar, with an r.m.s. deviation for the fitted atoms of 0.004 Å, as is the furan ring O3/C8—C11, with an r.m.s. deviation of 0.003 Å. The dihedral angle between these two planes is 4.2 (2)°. The O2/C7/N2/N1/C6 plane (r.m.s. deviation 0.035 Å) forms dihedral angles of 3.1 (1)° and 5.1 (1)°, respectively, with the O1/C2—C5 and O3/C8—C11 furan rings.
Intermolecular N—H···O hydrogen bonds link the molecules into chains running along the b axis. These chains are cross-linked via C—H···O hydrogen bonds (Table 1) forming a two-dimensional network structure, as illustrated in Fig. 2. In addition, π-π stacking interactions involving the inversion-related O3/C8—C11 furan rings, with a centroid-to-centroid distance of 3.4866 (14) Å is observed.