Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026633/hk2265sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026633/hk2265Isup2.hkl |
CCDC reference: 654916
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.127
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G 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 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see: Cimerman et al. (1997); Allen et al. (1987). For related literature, see: Tucker et al. (1975); Sutherland & Hoy (1968).
A mixture of acetyl furan (100 mmol) and acetohydrazide (100 mmol) was stirred in refluxing ethanol (30 ml) for 5 h to afford the title compound (yield; 87 mmol, 87%). Single crystals suitable for X-ray analysis were obtained by recrystallization from ethanol at room temperature.
H atom of NH group was located in difference syntheses and refined isotropically [N—H = 0.897 (9) Å and Uiso(H) = 0.048 (5) Å2]. The remaining H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for aromatic and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for aromatic H atoms.
Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Cimerman et al., 1997). As part of our ongoing studies on new Schiff base compounds, the title compound, (I), was synthesized and we herein report its crystal structure.
In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles are generally within normal ranges (Allen et al., 1987). The bonds C5—N1 [1.282 (2) Å] and C7—O2 [1.231 (2) Å] are reported as 1.287 Å (Tucker et al., 1975) and 1.298 Å (Sutherland & Hoy, 1968), respectively. The dihedral angle between the planar ring A (O1/C1—C4) and the planar moiety B (N1/N2/C4—C6) is A/B = 3.57 (3)°.
The intermolecular N—H···O hydrogen bonds (Table 1) seem to be effective in the stabilization of the crystal structure.
For general background, see: Cimerman et al. (1997); Allen et al. (1987). For related literature, see: Tucker et al. (1975); Sutherland & Hoy (1968).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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.
Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C8H10N2O2 | F(000) = 704 |
Mr = 166.18 | Dx = 1.311 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 876 reflections |
a = 23.865 (6) Å | θ = 2.5–26.4° |
b = 4.3199 (10) Å | µ = 0.10 mm−1 |
c = 16.829 (4) Å | T = 294 K |
β = 103.845 (4)° | Block, colorless |
V = 1684.5 (7) Å3 | 0.18 × 0.12 × 0.08 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 1153 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 26.4°, θmin = 2.5° |
φ and ω scans | h = −22→29 |
4474 measured reflections | k = −5→5 |
1729 independent reflections | l = −20→21 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0672P)2 + 0.2316P] where P = (Fo2 + 2Fc2)/3 |
1729 reflections | (Δ/σ)max < 0.001 |
115 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.18 e Å−3 |
C8H10N2O2 | V = 1684.5 (7) Å3 |
Mr = 166.18 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 23.865 (6) Å | µ = 0.10 mm−1 |
b = 4.3199 (10) Å | T = 294 K |
c = 16.829 (4) Å | 0.18 × 0.12 × 0.08 mm |
β = 103.845 (4)° |
Bruker SMART CCD area-detector diffractometer | 1153 reflections with I > 2σ(I) |
4474 measured reflections | Rint = 0.035 |
1729 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | 1 restraint |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.20 e Å−3 |
1729 reflections | Δρmin = −0.18 e Å−3 |
115 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 | 0.05967 (5) | 0.5388 (3) | 0.56109 (7) | 0.0488 (4) | |
O2 | 0.20044 (6) | −0.3371 (4) | 0.40832 (9) | 0.0627 (5) | |
N1 | 0.13897 (6) | 0.1667 (3) | 0.52494 (9) | 0.0400 (4) | |
N2 | 0.17937 (6) | −0.0211 (4) | 0.50190 (9) | 0.0438 (4) | |
C1 | 0.02654 (8) | 0.7266 (5) | 0.59583 (13) | 0.0538 (6) | |
H1 | −0.0103 | 0.7947 | 0.5702 | 0.065* | |
C2 | 0.05448 (9) | 0.7991 (5) | 0.67200 (13) | 0.0564 (6) | |
H2 | 0.0410 | 0.9236 | 0.7085 | 0.068* | |
C3 | 0.10853 (8) | 0.6499 (5) | 0.68635 (11) | 0.0483 (5) | |
H3 | 0.1375 | 0.6580 | 0.7343 | 0.058* | |
C4 | 0.11038 (7) | 0.4942 (4) | 0.61803 (10) | 0.0376 (4) | |
C5 | 0.15346 (8) | 0.2949 (4) | 0.59558 (11) | 0.0388 (4) | |
C6 | 0.20992 (8) | 0.2627 (5) | 0.65683 (13) | 0.0568 (6) | |
H6A | 0.2223 | 0.0508 | 0.6589 | 0.085* | |
H6B | 0.2055 | 0.3247 | 0.7098 | 0.085* | |
H6C | 0.2382 | 0.3919 | 0.6412 | 0.085* | |
C7 | 0.16446 (8) | −0.1763 (4) | 0.43065 (11) | 0.0434 (5) | |
C8 | 0.10414 (9) | −0.1486 (5) | 0.38123 (12) | 0.0595 (6) | |
H8A | 0.1003 | −0.2565 | 0.3303 | 0.089* | |
H8B | 0.0948 | 0.0659 | 0.3705 | 0.089* | |
H8C | 0.0783 | −0.2372 | 0.4109 | 0.089* | |
H2A | 0.2161 (5) | −0.046 (4) | 0.5298 (10) | 0.048 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0460 (8) | 0.0577 (9) | 0.0400 (7) | 0.0106 (6) | 0.0049 (6) | −0.0099 (6) |
O2 | 0.0556 (9) | 0.0730 (10) | 0.0607 (9) | 0.0218 (8) | 0.0162 (7) | −0.0114 (8) |
N1 | 0.0415 (8) | 0.0403 (8) | 0.0390 (8) | 0.0076 (7) | 0.0112 (6) | 0.0013 (7) |
N2 | 0.0384 (9) | 0.0457 (9) | 0.0463 (9) | 0.0112 (7) | 0.0085 (7) | −0.0015 (7) |
C1 | 0.0435 (11) | 0.0627 (13) | 0.0563 (13) | 0.0127 (10) | 0.0141 (10) | −0.0122 (11) |
C2 | 0.0527 (12) | 0.0689 (14) | 0.0521 (13) | 0.0002 (11) | 0.0214 (10) | −0.0195 (11) |
C3 | 0.0477 (11) | 0.0603 (13) | 0.0362 (10) | −0.0054 (9) | 0.0088 (8) | −0.0088 (9) |
C4 | 0.0387 (10) | 0.0383 (10) | 0.0349 (9) | −0.0012 (8) | 0.0073 (7) | 0.0009 (8) |
C5 | 0.0408 (10) | 0.0361 (10) | 0.0389 (10) | −0.0021 (8) | 0.0081 (8) | 0.0022 (8) |
C6 | 0.0460 (11) | 0.0628 (13) | 0.0560 (13) | 0.0085 (10) | 0.0009 (9) | −0.0110 (11) |
C7 | 0.0467 (11) | 0.0445 (11) | 0.0413 (10) | 0.0106 (9) | 0.0151 (9) | 0.0009 (9) |
C8 | 0.0574 (13) | 0.0734 (15) | 0.0434 (11) | 0.0186 (11) | 0.0038 (9) | −0.0121 (11) |
O1—C1 | 1.359 (2) | C3—C4 | 1.342 (2) |
O1—C4 | 1.366 (2) | C3—H3 | 0.9300 |
O2—C7 | 1.231 (2) | C4—C5 | 1.458 (2) |
N1—C5 | 1.282 (2) | C5—C6 | 1.494 (3) |
N1—N2 | 1.385 (2) | C6—H6A | 0.9600 |
N2—C7 | 1.345 (2) | C6—H6B | 0.9600 |
N2—H2A | 0.897 (9) | C6—H6C | 0.9600 |
C1—C2 | 1.333 (3) | C7—C8 | 1.485 (3) |
C1—H1 | 0.9300 | C8—H8A | 0.9600 |
C2—C3 | 1.410 (3) | C8—H8B | 0.9600 |
C2—H2 | 0.9300 | C8—H8C | 0.9600 |
C1—O1—C4 | 106.95 (14) | N1—C5—C6 | 126.74 (17) |
C5—N1—N2 | 117.48 (15) | C4—C5—C6 | 116.84 (16) |
C7—N2—N1 | 119.22 (15) | C5—C6—H6A | 109.5 |
C7—N2—H2A | 115.1 (12) | C5—C6—H6B | 109.5 |
N1—N2—H2A | 125.6 (12) | H6A—C6—H6B | 109.5 |
C2—C1—O1 | 110.20 (17) | C5—C6—H6C | 109.5 |
C2—C1—H1 | 124.9 | H6A—C6—H6C | 109.5 |
O1—C1—H1 | 124.9 | H6B—C6—H6C | 109.5 |
C1—C2—C3 | 106.50 (17) | O2—C7—N2 | 119.89 (17) |
C1—C2—H2 | 126.8 | O2—C7—C8 | 121.87 (18) |
C3—C2—H2 | 126.8 | N2—C7—C8 | 118.24 (16) |
C4—C3—C2 | 107.38 (17) | C7—C8—H8A | 109.5 |
C4—C3—H3 | 126.3 | C7—C8—H8B | 109.5 |
C2—C3—H3 | 126.3 | H8A—C8—H8B | 109.5 |
C3—C4—O1 | 108.98 (15) | C7—C8—H8C | 109.5 |
C3—C4—C5 | 133.45 (17) | H8A—C8—H8C | 109.5 |
O1—C4—C5 | 117.57 (15) | H8B—C8—H8C | 109.5 |
N1—C5—C4 | 116.42 (16) | ||
C5—N1—N2—C7 | 175.53 (16) | N2—N1—C5—C4 | 179.36 (14) |
C4—O1—C1—C2 | −0.3 (2) | N2—N1—C5—C6 | −0.2 (3) |
O1—C1—C2—C3 | 0.2 (2) | C3—C4—C5—N1 | 175.81 (19) |
C1—C2—C3—C4 | −0.1 (2) | O1—C4—C5—N1 | −2.9 (2) |
C2—C3—C4—O1 | 0.0 (2) | C3—C4—C5—C6 | −4.6 (3) |
C2—C3—C4—C5 | −178.84 (19) | O1—C4—C5—C6 | 176.71 (16) |
C1—O1—C4—C3 | 0.2 (2) | N1—N2—C7—O2 | 177.92 (16) |
C1—O1—C4—C5 | 179.20 (15) | N1—N2—C7—C8 | −2.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2i | 0.90 (1) | 2.08 (1) | 2.968 (2) | 173 (2) |
Symmetry code: (i) −x+1/2, −y−1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C8H10N2O2 |
Mr | 166.18 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 23.865 (6), 4.3199 (10), 16.829 (4) |
β (°) | 103.845 (4) |
V (Å3) | 1684.5 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.18 × 0.12 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4474, 1729, 1153 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.127, 1.03 |
No. of reflections | 1729 |
No. of parameters | 115 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.18 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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···O2i | 0.897 (9) | 2.076 (10) | 2.968 (2) | 172.7 (17) |
Symmetry code: (i) −x+1/2, −y−1/2, −z+1. |
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Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Cimerman et al., 1997). As part of our ongoing studies on new Schiff base compounds, the title compound, (I), was synthesized and we herein report its crystal structure.
In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles are generally within normal ranges (Allen et al., 1987). The bonds C5—N1 [1.282 (2) Å] and C7—O2 [1.231 (2) Å] are reported as 1.287 Å (Tucker et al., 1975) and 1.298 Å (Sutherland & Hoy, 1968), respectively. The dihedral angle between the planar ring A (O1/C1—C4) and the planar moiety B (N1/N2/C4—C6) is A/B = 3.57 (3)°.
The intermolecular N—H···O hydrogen bonds (Table 1) seem to be effective in the stabilization of the crystal structure.