organic compounds
The molecule of the title compound, C12H10N2O4, is planar and two molecules are stacked over one another at a distance of 3.6 Å. The molecules are linked by hydrogen bonds into a three-dimensional network.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008391/bt6627sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008391/bt6627Isup2.hkl |
CCDC reference: 270244
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
3-Hydroxysalicylaldehyde 2-furoylhydrazone top
Crystal data top
C12H10N2O4 | F(000) = 512 |
Mr = 246.22 | Dx = 1.443 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2381 reflections |
a = 11.2143 (8) Å | θ = 2.2–27.0° |
b = 9.3730 (7) Å | µ = 0.11 mm−1 |
c = 11.4149 (9) Å | T = 295 K |
β = 109.120 (1)° | Plate, yellow |
V = 1133.7 (2) Å3 | 0.42 × 0.32 × 0.14 mm |
Z = 4 |
Data collection top
Bruker SMART area-detector diffractometer | 1703 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 27.0°, θmin = 2.2° |
φ and ω scans | h = −13→14 |
6280 measured reflections | k = −11→11 |
2461 independent reflections | l = −9→14 |
Refinement top
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)] = 0.041 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.127 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0624P)2 + 0.2675P] where P = (Fo2 + 2Fc2)/3 |
2461 reflections | (Δ/σ)max = 0.001 |
203 parameters | Δρmax = 0.24 e Å−3 |
10 restraints | Δρmin = −0.23 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.1404 (1) | 0.5056 (2) | 0.2430 (1) | 0.0577 (4) | |
O2 | 0.3382 (1) | 0.6684 (1) | 0.2996 (1) | 0.0552 (4) | |
O3 | 0.6001 (1) | 0.9299 (2) | 0.3082 (1) | 0.0575 (4) | |
O4 | 0.7896 (1) | 1.1196 (2) | 0.3735 (1) | 0.0724 (5) | |
N1 | 0.5279 (1) | 0.7832 (2) | 0.4721 (1) | 0.0450 (4) | |
N2 | 0.6314 (1) | 0.8709 (2) | 0.5084 (1) | 0.0465 (4) | |
C1 | 0.3156 (2) | 0.6016 (2) | 0.3959 (1) | 0.0404 (4) | |
C2 | 0.2104 (2) | 0.5132 (2) | 0.3661 (2) | 0.0440 (4) | |
C3 | 0.1818 (2) | 0.4399 (2) | 0.4575 (2) | 0.0572 (5) | |
C4 | 0.2556 (2) | 0.4551 (2) | 0.5803 (2) | 0.0630 (6) | |
C5 | 0.3587 (2) | 0.5432 (2) | 0.6110 (2) | 0.0553 (5) | |
C6 | 0.3909 (2) | 0.6187 (2) | 0.5201 (2) | 0.0422 (4) | |
C7 | 0.5002 (2) | 0.7123 (2) | 0.5555 (2) | 0.0460 (4) | |
C8 | 0.6607 (2) | 0.9423 (2) | 0.4194 (1) | 0.0419 (4) | |
C9 | 0.7689 (2) | 1.0381 (2) | 0.4633 (2) | 0.0437 (4) | |
C10 | 0.8530 (2) | 1.0716 (2) | 0.5733 (2) | 0.0590 (5) | |
C11 | 0.9319 (2) | 1.1782 (3) | 0.5512 (2) | 0.0688 (6) | |
C12 | 0.8894 (2) | 1.2032 (3) | 0.4309 (2) | 0.0771 (7) | |
H1o | 0.067 (1) | 0.473 (2) | 0.235 (2) | 0.083 (8)* | |
H2o | 0.402 (2) | 0.723 (2) | 0.330 (2) | 0.096 (9)* | |
H2n | 0.668 (2) | 0.884 (2) | 0.586 (1) | 0.063 (6)* | |
H3 | 0.110 (1) | 0.380 (2) | 0.436 (2) | 0.076 (7)* | |
H4 | 0.234 (2) | 0.406 (2) | 0.643 (2) | 0.077 (7)* | |
H5 | 0.407 (2) | 0.556 (2) | 0.697 (1) | 0.065 (6)* | |
H7 | 0.551 (2) | 0.719 (2) | 0.641 (1) | 0.052 (5)* | |
H10 | 0.857 (2) | 1.032 (2) | 0.650 (1) | 0.066 (6)* | |
H11 | 1.003 (2) | 1.224 (2) | 0.608 (2) | 0.075 (6)* | |
H12 | 0.915 (2) | 1.269 (2) | 0.379 (2) | 0.093 (8)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.055 (1) | 0.073 (1) | 0.034 (1) | −0.020 (1) | 0.000 (1) | 0.003 (1) |
O2 | 0.068 (1) | 0.063 (1) | 0.032 (1) | −0.024 (1) | 0.013 (1) | −0.001 (1) |
O3 | 0.048 (1) | 0.085 (1) | 0.034 (1) | −0.010 (1) | 0.007 (1) | −0.008 (1) |
O4 | 0.070 (1) | 0.103 (1) | 0.041 (1) | −0.034 (1) | 0.013 (1) | 0.005 (1) |
N1 | 0.043 (1) | 0.049 (1) | 0.040 (1) | −0.009 (1) | 0.010 (1) | −0.008 (1) |
N2 | 0.046 (1) | 0.054 (1) | 0.034 (1) | −0.012 (1) | 0.006 (1) | −0.007 (1) |
C1 | 0.045 (1) | 0.042 (1) | 0.032 (1) | −0.002 (1) | 0.011 (1) | 0.001 (1) |
C2 | 0.044 (1) | 0.051 (1) | 0.032 (1) | −0.004 (1) | 0.006 (1) | 0.001 (1) |
C3 | 0.053 (1) | 0.070 (1) | 0.044 (1) | −0.021 (1) | 0.009 (1) | 0.004 (1) |
C4 | 0.067 (1) | 0.081 (1) | 0.039 (1) | −0.020 (1) | 0.015 (1) | 0.011 (1) |
C5 | 0.059 (1) | 0.070 (1) | 0.031 (1) | −0.010 (1) | 0.006 (1) | 0.002 (1) |
C6 | 0.043 (1) | 0.046 (1) | 0.034 (1) | −0.002 (1) | 0.008 (1) | −0.002 (1) |
C7 | 0.046 (1) | 0.052 (1) | 0.035 (1) | −0.005 (1) | 0.007 (1) | −0.006 (1) |
C8 | 0.037 (1) | 0.052 (1) | 0.035 (1) | 0.002 (1) | 0.010 (1) | −0.005 (1) |
C9 | 0.040 (1) | 0.054 (1) | 0.036 (1) | −0.002 (1) | 0.012 (1) | 0.001 (1) |
C10 | 0.054 (1) | 0.073 (1) | 0.042 (1) | −0.016 (1) | 0.005 (1) | 0.006 (1) |
C11 | 0.057 (1) | 0.082 (2) | 0.058 (1) | −0.025 (1) | 0.005 (1) | 0.002 (1) |
C12 | 0.070 (1) | 0.099 (2) | 0.060 (1) | −0.038 (1) | 0.018 (1) | 0.006 (1) |
Geometric parameters (Å, º) top
O1—C2 | 1.368 (2) | C6—C7 | 1.453 (2) |
O2—C1 | 1.359 (2) | C8—C9 | 1.460 (2) |
O3—C8 | 1.233 (2) | C9—C10 | 1.338 (2) |
O4—C9 | 1.358 (2) | C10—C11 | 1.411 (3) |
O4—C12 | 1.348 (3) | C11—C12 | 1.319 (3) |
N1—N2 | 1.371 (2) | O1—H1o | 0.86 (10) |
N1—C7 | 1.280 (2) | O2—H2o | 0.86 (1) |
N2—C8 | 1.344 (2) | N2—H2n | 0.85 (1) |
C1—C2 | 1.390 (2) | C3—H3 | 0.95 (1) |
C1—C6 | 1.402 (2) | C4—H4 | 0.95 (1) |
C2—C3 | 1.372 (2) | C7—H7 | 0.95 (1) |
C3—C4 | 1.382 (3) | C10—H10 | 0.94 (1) |
C4—C5 | 1.370 (3) | C11—H11 | 0.95 (1) |
C5—C6 | 1.397 (2) | C12—H12 | 0.96 (1) |
C5—H5 | 0.955 (9) | ||
C9—O4—C12 | 106.3 (2) | C9—C10—C11 | 106.8 (2) |
N2—N1—C7 | 118.3 (1) | C12—C11—C10 | 106.2 (2) |
N1—N2—C8 | 117.5 (1) | C11—C12—O4 | 111.2 (2) |
O2—C1—C2 | 116.4 (1) | C2—O1—H1o | 110 (2) |
O2—C1—C6 | 123.8 (1) | C1—O2—H2o | 107 (2) |
C2—C1—C6 | 119.8 (1) | C8—N2—H2n | 124 (1) |
O1—C2—C3 | 123.8 (2) | N1—N2—H2n | 118 (1) |
O1—C2—C1 | 116.0 (1) | C2—C3—H3 | 119 (1) |
C3—C2—C1 | 120.3 (2) | C4—C3—H3 | 120 (1) |
C2—C3—C4 | 120.5 (2) | C5—C4—H4 | 120 (1) |
C4—C5—C6 | 121.1 (2) | C3—C4—H4 | 120 (1) |
C5—C4—C3 | 119.8 (2) | C4—C5—H5 | 119 (1) |
C5—C6—C1 | 118.5 (2) | C6—C5—H5 | 120 (1) |
C5—C6—C7 | 120.0 (2) | N1—C7—H7 | 121 (1) |
C1—C6—C7 | 121.6 (2) | C6—C7—H7 | 119 (1) |
N1—C7—C6 | 119.7 (2) | C9—C10—H10 | 126 (1) |
O3—C8—N2 | 122.8 (2) | C11—C10—H10 | 127 (1) |
O3—C8—C9 | 121.8 (2) | C12—C11—H11 | 124 (1) |
N2—C8—C9 | 115.3 (1) | C10—C11—H11 | 130 (1) |
O4—C9—C8 | 114.5 (1) | C11—C12—H12 | 133 (2) |
O4—C9—C10 | 109.5 (2) | O4—C12—H12 | 116 (2) |
C10—C9—C8 | 135.9 (2) | ||
C1—C6—C7—N1 | 1.3 (3) | O2—C1—C6—C5 | −179.4 (2) |
C7—N1—N2—C8 | 178.6 (2) | C2—C1—C6—C5 | 1.2 (3) |
C6—C7—N1—N2 | 179.8 (2) | O2—C1—C6—C7 | 0.6 (3) |
N1—N2—C8—O3 | −1.3 (2) | C2—C1—C6—C7 | −178.8 (2) |
N1—N2—C8—C9 | 177.8 (1) | C5—C6—C7—N1 | −178.7 (2) |
O3—C8—C9—O4 | 5.3 (2) | C12—O4—C9—C10 | 0.6 (2) |
O2—C1—C2—O1 | −1.1 (2) | C12—O4—C9—C8 | 178.2 (2) |
C6—C1—C2—O1 | 178.3 (2) | O3—C8—C9—C10 | −178.0 (2) |
O2—C1—C2—C3 | 179.0 (2) | N2—C8—C9—C10 | 2.9 (3) |
C6—C1—C2—C3 | −1.6 (3) | N2—C8—C9—O4 | −173.8 (2) |
O1—C2—C3—C4 | −178.7 (2) | O4—C9—C10—C11 | −0.9 (2) |
C1—C2—C3—C4 | 1.2 (3) | C8—C9—C10—C11 | −177.8 (2) |
C2—C3—C4—C5 | −0.4 (3) | C9—C10—C11—C12 | 0.9 (3) |
C3—C4—C5—C6 | 0.0 (3) | C10—C11—C12—O4 | −0.6 (3) |
C4—C5—C6—C1 | −0.4 (3) | C9—O4—C12—C11 | 0.0 (3) |
C4—C5—C6—C7 | 179.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···O3i | 0.86 (1) | 1.82 (1) | 2.662 (2) | 169 (2) |
O2—H2o···N1 | 0.86 (1) | 1.85 (2) | 2.611 (2) | 147 (2) |
N2—H2n···O1ii | 0.85 (1) | 2.18 (2) | 2.890 (2) | 141 (2) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x+1/2, −y+3/2, z+1/2. |