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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008391/bt6627sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008391/bt6627Isup2.hkl
Contains datablock I

CCDC reference: 270244

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.127
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT731_ALERT_1_B Bond Calc 0.854(14), Rep 0.86(10) ...... 7.14 su-Rat O1 -H1O 1.555 1.555
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.08
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

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
C12H10N2O4F(000) = 512
Mr = 246.22Dx = 1.443 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2381 reflections
a = 11.2143 (8) Åθ = 2.2–27.0°
b = 9.3730 (7) ŵ = 0.11 mm1
c = 11.4149 (9) ÅT = 295 K
β = 109.120 (1)°Plate, yellow
V = 1133.7 (2) Å30.42 × 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 tubeRint = 0.020
Graphite monochromatorθmax = 27.0°, θmin = 2.2°
φ and ω scansh = 1314
6280 measured reflectionsk = 1111
2461 independent reflectionsl = 914
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: difference Fourier map
wR(F2) = 0.127All 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 parametersΔρmax = 0.24 e Å3
10 restraintsΔρmin = 0.23 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1404 (1)0.5056 (2)0.2430 (1)0.0577 (4)
O20.3382 (1)0.6684 (1)0.2996 (1)0.0552 (4)
O30.6001 (1)0.9299 (2)0.3082 (1)0.0575 (4)
O40.7896 (1)1.1196 (2)0.3735 (1)0.0724 (5)
N10.5279 (1)0.7832 (2)0.4721 (1)0.0450 (4)
N20.6314 (1)0.8709 (2)0.5084 (1)0.0465 (4)
C10.3156 (2)0.6016 (2)0.3959 (1)0.0404 (4)
C20.2104 (2)0.5132 (2)0.3661 (2)0.0440 (4)
C30.1818 (2)0.4399 (2)0.4575 (2)0.0572 (5)
C40.2556 (2)0.4551 (2)0.5803 (2)0.0630 (6)
C50.3587 (2)0.5432 (2)0.6110 (2)0.0553 (5)
C60.3909 (2)0.6187 (2)0.5201 (2)0.0422 (4)
C70.5002 (2)0.7123 (2)0.5555 (2)0.0460 (4)
C80.6607 (2)0.9423 (2)0.4194 (1)0.0419 (4)
C90.7689 (2)1.0381 (2)0.4633 (2)0.0437 (4)
C100.8530 (2)1.0716 (2)0.5733 (2)0.0590 (5)
C110.9319 (2)1.1782 (3)0.5512 (2)0.0688 (6)
C120.8894 (2)1.2032 (3)0.4309 (2)0.0771 (7)
H1o0.067 (1)0.473 (2)0.235 (2)0.083 (8)*
H2o0.402 (2)0.723 (2)0.330 (2)0.096 (9)*
H2n0.668 (2)0.884 (2)0.586 (1)0.063 (6)*
H30.110 (1)0.380 (2)0.436 (2)0.076 (7)*
H40.234 (2)0.406 (2)0.643 (2)0.077 (7)*
H50.407 (2)0.556 (2)0.697 (1)0.065 (6)*
H70.551 (2)0.719 (2)0.641 (1)0.052 (5)*
H100.857 (2)1.032 (2)0.650 (1)0.066 (6)*
H111.003 (2)1.224 (2)0.608 (2)0.075 (6)*
H120.915 (2)1.269 (2)0.379 (2)0.093 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.055 (1)0.073 (1)0.034 (1)0.020 (1)0.000 (1)0.003 (1)
O20.068 (1)0.063 (1)0.032 (1)0.024 (1)0.013 (1)0.001 (1)
O30.048 (1)0.085 (1)0.034 (1)0.010 (1)0.007 (1)0.008 (1)
O40.070 (1)0.103 (1)0.041 (1)0.034 (1)0.013 (1)0.005 (1)
N10.043 (1)0.049 (1)0.040 (1)0.009 (1)0.010 (1)0.008 (1)
N20.046 (1)0.054 (1)0.034 (1)0.012 (1)0.006 (1)0.007 (1)
C10.045 (1)0.042 (1)0.032 (1)0.002 (1)0.011 (1)0.001 (1)
C20.044 (1)0.051 (1)0.032 (1)0.004 (1)0.006 (1)0.001 (1)
C30.053 (1)0.070 (1)0.044 (1)0.021 (1)0.009 (1)0.004 (1)
C40.067 (1)0.081 (1)0.039 (1)0.020 (1)0.015 (1)0.011 (1)
C50.059 (1)0.070 (1)0.031 (1)0.010 (1)0.006 (1)0.002 (1)
C60.043 (1)0.046 (1)0.034 (1)0.002 (1)0.008 (1)0.002 (1)
C70.046 (1)0.052 (1)0.035 (1)0.005 (1)0.007 (1)0.006 (1)
C80.037 (1)0.052 (1)0.035 (1)0.002 (1)0.010 (1)0.005 (1)
C90.040 (1)0.054 (1)0.036 (1)0.002 (1)0.012 (1)0.001 (1)
C100.054 (1)0.073 (1)0.042 (1)0.016 (1)0.005 (1)0.006 (1)
C110.057 (1)0.082 (2)0.058 (1)0.025 (1)0.005 (1)0.002 (1)
C120.070 (1)0.099 (2)0.060 (1)0.038 (1)0.018 (1)0.006 (1)
Geometric parameters (Å, º) top
O1—C21.368 (2)C6—C71.453 (2)
O2—C11.359 (2)C8—C91.460 (2)
O3—C81.233 (2)C9—C101.338 (2)
O4—C91.358 (2)C10—C111.411 (3)
O4—C121.348 (3)C11—C121.319 (3)
N1—N21.371 (2)O1—H1o0.86 (10)
N1—C71.280 (2)O2—H2o0.86 (1)
N2—C81.344 (2)N2—H2n0.85 (1)
C1—C21.390 (2)C3—H30.95 (1)
C1—C61.402 (2)C4—H40.95 (1)
C2—C31.372 (2)C7—H70.95 (1)
C3—C41.382 (3)C10—H100.94 (1)
C4—C51.370 (3)C11—H110.95 (1)
C5—C61.397 (2)C12—H120.96 (1)
C5—H50.955 (9)
C9—O4—C12106.3 (2)C9—C10—C11106.8 (2)
N2—N1—C7118.3 (1)C12—C11—C10106.2 (2)
N1—N2—C8117.5 (1)C11—C12—O4111.2 (2)
O2—C1—C2116.4 (1)C2—O1—H1o110 (2)
O2—C1—C6123.8 (1)C1—O2—H2o107 (2)
C2—C1—C6119.8 (1)C8—N2—H2n124 (1)
O1—C2—C3123.8 (2)N1—N2—H2n118 (1)
O1—C2—C1116.0 (1)C2—C3—H3119 (1)
C3—C2—C1120.3 (2)C4—C3—H3120 (1)
C2—C3—C4120.5 (2)C5—C4—H4120 (1)
C4—C5—C6121.1 (2)C3—C4—H4120 (1)
C5—C4—C3119.8 (2)C4—C5—H5119 (1)
C5—C6—C1118.5 (2)C6—C5—H5120 (1)
C5—C6—C7120.0 (2)N1—C7—H7121 (1)
C1—C6—C7121.6 (2)C6—C7—H7119 (1)
N1—C7—C6119.7 (2)C9—C10—H10126 (1)
O3—C8—N2122.8 (2)C11—C10—H10127 (1)
O3—C8—C9121.8 (2)C12—C11—H11124 (1)
N2—C8—C9115.3 (1)C10—C11—H11130 (1)
O4—C9—C8114.5 (1)C11—C12—H12133 (2)
O4—C9—C10109.5 (2)O4—C12—H12116 (2)
C10—C9—C8135.9 (2)
C1—C6—C7—N11.3 (3)O2—C1—C6—C5179.4 (2)
C7—N1—N2—C8178.6 (2)C2—C1—C6—C51.2 (3)
C6—C7—N1—N2179.8 (2)O2—C1—C6—C70.6 (3)
N1—N2—C8—O31.3 (2)C2—C1—C6—C7178.8 (2)
N1—N2—C8—C9177.8 (1)C5—C6—C7—N1178.7 (2)
O3—C8—C9—O45.3 (2)C12—O4—C9—C100.6 (2)
O2—C1—C2—O11.1 (2)C12—O4—C9—C8178.2 (2)
C6—C1—C2—O1178.3 (2)O3—C8—C9—C10178.0 (2)
O2—C1—C2—C3179.0 (2)N2—C8—C9—C102.9 (3)
C6—C1—C2—C31.6 (3)N2—C8—C9—O4173.8 (2)
O1—C2—C3—C4178.7 (2)O4—C9—C10—C110.9 (2)
C1—C2—C3—C41.2 (3)C8—C9—C10—C11177.8 (2)
C2—C3—C4—C50.4 (3)C9—C10—C11—C120.9 (3)
C3—C4—C5—C60.0 (3)C10—C11—C12—O40.6 (3)
C4—C5—C6—C10.4 (3)C9—O4—C12—C110.0 (3)
C4—C5—C6—C7179.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O3i0.86 (1)1.82 (1)2.662 (2)169 (2)
O2—H2o···N10.86 (1)1.85 (2)2.611 (2)147 (2)
N2—H2n···O1ii0.85 (1)2.18 (2)2.890 (2)141 (2)
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+1/2, y+3/2, z+1/2.
 

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