organic compounds
N′-[(E)-Furan-2-ylmethylidene]pyridine-3-carbohydrazide
aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
*Correspondence e-mail: eesans@yahoo.com
The title compound, C11H9N3O2, exists in the E conformation with respect to the azomethane C=N bond, and has the keto form. There are two independent molecules in the and each of these features a slight slanting of the pyridine and furan rings, which form a dihedral angle of 14.96 (10)° in one of the molecules and 5.53 (10)° in the other. The is stabilized by N—H⋯O and N—H⋯N hydrogen bonds, weak C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π interactions and π–π interactions [shortest centroid–centroid distance = 3.7864 (15) Å].
Related literature
For applications of carbohydrazide in non-linear optics and molecular sensing, see: Bakir & Brown (2002). For the synthesis of related compounds, see: Fun et al. (2008); Neema & Kurup (2011). For similar structures, see: Nancy et al. (2011). For standard bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536811046381/tk5012sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046381/tk5012Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811046381/tk5012Isup3.cml
The title compound, (I), was prepared by adapting a reported procedure (Fun et al., 2008) by refluxing a mixture of a methanol solutions of furan-2-carboxaldehyde (0.960 g, 10 mmol) and pyridine-3-carbohydrazide (1.370 g, 10 mmol) for 3 h. The formed crystals were collected and recrystallized from a mixture of ethanol and dimethylformamide (1:1 v/v). Light-green crystals were obtained.
All C-bound H atoms were placed in calculated positions with C—H = 0.93 Å, and with Uiso=1.2Ueq(C). The N-bound H atoms were refined with N—H = 0.88±0.1 Å and free Uiso.
Derivatives of pyridine-3-carbohydrazide and their metal complexes possess pronounced biological activities. They also contain versatile binding properties and the presence of the carbonyl-O atom promotes the the formation of a chelate binding center (Neema & Kurup, 2011). Derivatives of pyridine-3-carbohydrazide and their metal complexes have received considerable attention during the last decade because of their versatile applications in nonlinear optics and molecular sensing (Bakir & Brown, 2002). The present report is an extension of earlier studies in this area (Nancy et al., 2011).
The title compound, (I), crystallizes in triclinic 1.There are two independent molecules (Fig. 1) in the with almost the same bond length and bond angle, and therefore the detailed description can be limited to one of these molecules. The molecule adopts an E configuration with respect to C7═N3 bond and it exists in the keto form with C6═O1 bond length of 1.226 (2) Å which is very close to a formal C═O bond length [1.21 Å] (Allen et al., 1987). The dihedral angle between pyridine and furan rings is 14.96 (10)°. The O1 and N3 atoms are syn with respect to the C6—N2 bond having a torsion angle of -2.0 (3)°. The molecule is almost planar with maximum deviation of 0.265 (2) Å for atom C2; the other molecule has the maximum deviation of 0.212 (1) Å for the atom O3 from its least-squares plane.
PConventional N—H···O,N hydrogen bonds are present, Table 1, Moreover, there are non-conventional intermolecular interactions present in the
Table 1, which contribute to the formation of a 3-D network.Fig. 2 shows a partial packing diagram. The molecules shown participate in C–H···π interactions formed between the H atoms attached at the C10 and C12 atoms and the furan rings, Table 1. The presence of π–π interactions, with centroid-centroid distances of 3.7864 (15), 3.7864 (15), 3.7274 (15) and 3.7273 (15) Å between the rings, is also noted.
For applications of carbohydrazide in non-linear optics and molecular sensing, see: Bakir & Brown (2002). For the synthesis of related compounds, see: Fun et al. (2008); Neema & Kurup (2011). For similar structures, see: Nancy et al. (2011). For standard bond-length data, see: Allen et al. (1987).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell
CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. | |
Fig. 2. A view of the unit cell for (I). |
C11H9N3O2 | Z = 4 |
Mr = 215.21 | F(000) = 448 |
Triclinic, P1 | Dx = 1.398 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.441 (2) Å | Cell parameters from 2702 reflections |
b = 10.237 (3) Å | θ = 3.0–25.0° |
c = 11.023 (2) Å | µ = 0.10 mm−1 |
α = 75.10 (2)° | T = 150 K |
β = 85.413 (19)° | Block, light-green |
γ = 84.11 (2)° | 0.26 × 0.21 × 0.18 mm |
V = 1022.5 (4) Å3 |
Bruker P4 diffractometer | 3589 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2702 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −12→11 |
Tmin = 0.975, Tmax = 0.982 | l = −12→13 |
9430 measured reflections |
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)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0674P)2 + 0.0667P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
3589 reflections | Δρmax = 0.22 e Å−3 |
298 parameters | Δρmin = −0.29 e Å−3 |
2 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.008 (2) |
C11H9N3O2 | γ = 84.11 (2)° |
Mr = 215.21 | V = 1022.5 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.441 (2) Å | Mo Kα radiation |
b = 10.237 (3) Å | µ = 0.10 mm−1 |
c = 11.023 (2) Å | T = 150 K |
α = 75.10 (2)° | 0.26 × 0.21 × 0.18 mm |
β = 85.413 (19)° |
Bruker P4 diffractometer | 3589 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | 2702 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.982 | Rint = 0.023 |
9430 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 2 restraints |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.22 e Å−3 |
3589 reflections | Δρmin = −0.29 e Å−3 |
298 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 | 0.61774 (13) | −0.01358 (13) | 0.71738 (12) | 0.0408 (4) | |
O2 | 1.11415 (15) | 0.10175 (14) | 0.58530 (13) | 0.0488 (4) | |
O3 | 0.76963 (14) | 0.26997 (12) | 0.97572 (11) | 0.0373 (3) | |
O4 | 0.43780 (16) | 0.54591 (14) | 0.67271 (14) | 0.0557 (4) | |
N1 | 0.32366 (15) | 0.25812 (14) | 0.94601 (14) | 0.0331 (4) | |
N2 | 0.71582 (15) | 0.15648 (15) | 0.76984 (13) | 0.0293 (4) | |
N3 | 0.84450 (15) | 0.13134 (15) | 0.70761 (13) | 0.0306 (4) | |
N4 | 1.00763 (16) | 0.47023 (16) | 1.23845 (14) | 0.0368 (4) | |
N5 | 0.70930 (14) | 0.49236 (15) | 0.96475 (13) | 0.0268 (3) | |
N6 | 0.62315 (15) | 0.50278 (15) | 0.86641 (13) | 0.0283 (3) | |
C1 | 0.2301 (2) | 0.16377 (19) | 0.97664 (17) | 0.0355 (4) | |
H1 | 0.1473 | 0.1808 | 1.0237 | 0.043* | |
C2 | 0.24961 (19) | 0.04281 (18) | 0.94233 (17) | 0.0329 (4) | |
H2 | 0.1806 | −0.0191 | 0.9640 | 0.039* | |
C3 | 0.37305 (18) | 0.01569 (17) | 0.87553 (16) | 0.0307 (4) | |
H3 | 0.3890 | −0.0656 | 0.8516 | 0.037* | |
C4 | 0.47390 (18) | 0.10983 (17) | 0.84378 (15) | 0.0267 (4) | |
C5 | 0.44343 (18) | 0.23048 (17) | 0.88037 (16) | 0.0300 (4) | |
H5 | 0.5096 | 0.2951 | 0.8581 | 0.036* | |
C6 | 0.60870 (18) | 0.07795 (17) | 0.77142 (16) | 0.0288 (4) | |
C7 | 0.94024 (19) | 0.21070 (18) | 0.71100 (16) | 0.0316 (4) | |
H7 | 0.9194 | 0.2776 | 0.7546 | 0.038* | |
C8 | 1.07818 (19) | 0.19826 (19) | 0.64918 (16) | 0.0337 (4) | |
C9 | 1.18880 (17) | 0.27331 (18) | 0.64346 (15) | 0.0294 (4) | |
H9 | 1.1906 | 0.3450 | 0.6806 | 0.035* | |
C10 | 1.3003 (2) | 0.2241 (2) | 0.57180 (17) | 0.0404 (5) | |
H10 | 1.3897 | 0.2571 | 0.5519 | 0.049* | |
C11 | 1.2542 (2) | 0.1210 (2) | 0.53733 (18) | 0.0458 (5) | |
H11 | 1.3072 | 0.0695 | 0.4886 | 0.055* | |
C12 | 1.0577 (2) | 0.3466 (2) | 1.30061 (17) | 0.0386 (5) | |
H12 | 1.1209 | 0.3400 | 1.3629 | 0.046* | |
C13 | 1.0218 (2) | 0.2281 (2) | 1.27846 (18) | 0.0397 (5) | |
H13 | 1.0602 | 0.1442 | 1.3241 | 0.048* | |
C14 | 0.92747 (19) | 0.23689 (18) | 1.18683 (16) | 0.0340 (4) | |
H14 | 0.9003 | 0.1585 | 1.1706 | 0.041* | |
C15 | 0.87333 (17) | 0.36337 (17) | 1.11913 (15) | 0.0262 (4) | |
C16 | 0.91764 (18) | 0.47580 (18) | 1.14965 (16) | 0.0318 (4) | |
H16 | 0.8819 | 0.5611 | 1.1048 | 0.038* | |
C17 | 0.77872 (18) | 0.37120 (17) | 1.01468 (15) | 0.0267 (4) | |
C18 | 0.57217 (18) | 0.62304 (18) | 0.81434 (16) | 0.0293 (4) | |
H18 | 0.5977 | 0.6954 | 0.8421 | 0.035* | |
C19 | 0.47684 (18) | 0.64921 (18) | 0.71446 (16) | 0.0316 (4) | |
C20 | 0.41102 (18) | 0.76644 (18) | 0.65139 (15) | 0.0302 (4) | |
H20 | 0.4195 | 0.8518 | 0.6636 | 0.036* | |
C21 | 0.32700 (19) | 0.7377 (2) | 0.56365 (17) | 0.0369 (5) | |
H21 | 0.2697 | 0.7994 | 0.5068 | 0.044* | |
C22 | 0.3457 (2) | 0.6057 (2) | 0.5781 (2) | 0.0546 (6) | |
H22 | 0.3028 | 0.5586 | 0.5312 | 0.066* | |
H2N | 0.7125 (19) | 0.2127 (17) | 0.8202 (16) | 0.035 (5)* | |
H5N | 0.713 (2) | 0.5638 (17) | 0.9912 (18) | 0.043 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0418 (8) | 0.0409 (8) | 0.0502 (8) | −0.0061 (6) | 0.0002 (6) | −0.0300 (7) |
O2 | 0.0606 (9) | 0.0428 (9) | 0.0435 (8) | −0.0036 (7) | −0.0011 (7) | −0.0126 (7) |
O3 | 0.0526 (8) | 0.0267 (7) | 0.0372 (7) | −0.0020 (6) | −0.0121 (6) | −0.0139 (6) |
O4 | 0.0671 (10) | 0.0386 (9) | 0.0648 (10) | −0.0073 (7) | −0.0282 (8) | −0.0108 (7) |
N1 | 0.0369 (9) | 0.0286 (9) | 0.0363 (9) | 0.0003 (7) | −0.0034 (7) | −0.0137 (7) |
N2 | 0.0332 (8) | 0.0302 (9) | 0.0293 (8) | −0.0044 (7) | −0.0002 (6) | −0.0158 (7) |
N3 | 0.0342 (8) | 0.0318 (9) | 0.0273 (8) | −0.0021 (7) | −0.0019 (6) | −0.0105 (6) |
N4 | 0.0373 (9) | 0.0377 (10) | 0.0394 (9) | −0.0021 (7) | −0.0085 (7) | −0.0152 (8) |
N5 | 0.0296 (8) | 0.0256 (9) | 0.0286 (8) | −0.0016 (6) | −0.0047 (6) | −0.0126 (7) |
N6 | 0.0290 (8) | 0.0300 (9) | 0.0282 (8) | −0.0037 (6) | −0.0042 (6) | −0.0105 (6) |
C1 | 0.0370 (10) | 0.0353 (11) | 0.0354 (10) | −0.0026 (9) | 0.0004 (8) | −0.0118 (9) |
C2 | 0.0356 (10) | 0.0267 (10) | 0.0360 (10) | −0.0059 (8) | −0.0032 (8) | −0.0057 (8) |
C3 | 0.0394 (10) | 0.0224 (10) | 0.0327 (10) | −0.0017 (8) | −0.0051 (8) | −0.0107 (8) |
C4 | 0.0340 (10) | 0.0250 (9) | 0.0230 (9) | −0.0010 (7) | −0.0075 (7) | −0.0081 (7) |
C5 | 0.0325 (10) | 0.0282 (10) | 0.0317 (10) | −0.0041 (8) | −0.0060 (8) | −0.0102 (8) |
C6 | 0.0351 (10) | 0.0265 (10) | 0.0272 (9) | −0.0011 (8) | −0.0061 (7) | −0.0102 (8) |
C7 | 0.0375 (10) | 0.0317 (10) | 0.0282 (10) | −0.0046 (8) | −0.0023 (8) | −0.0110 (8) |
C8 | 0.0403 (11) | 0.0367 (11) | 0.0250 (9) | −0.0016 (8) | −0.0045 (8) | −0.0090 (8) |
C9 | 0.0281 (9) | 0.0377 (11) | 0.0271 (9) | −0.0072 (8) | −0.0001 (7) | −0.0151 (8) |
C10 | 0.0329 (10) | 0.0528 (13) | 0.0329 (10) | −0.0011 (9) | −0.0028 (8) | −0.0065 (9) |
C11 | 0.0503 (13) | 0.0470 (13) | 0.0343 (11) | 0.0125 (10) | 0.0017 (9) | −0.0076 (10) |
C12 | 0.0370 (11) | 0.0459 (13) | 0.0347 (11) | 0.0010 (9) | −0.0094 (8) | −0.0132 (9) |
C13 | 0.0501 (12) | 0.0345 (11) | 0.0344 (10) | 0.0041 (9) | −0.0126 (9) | −0.0084 (8) |
C14 | 0.0433 (11) | 0.0295 (11) | 0.0319 (10) | −0.0020 (8) | −0.0030 (8) | −0.0127 (8) |
C15 | 0.0268 (9) | 0.0270 (10) | 0.0262 (9) | −0.0006 (7) | 0.0017 (7) | −0.0105 (7) |
C16 | 0.0348 (10) | 0.0290 (10) | 0.0329 (10) | −0.0011 (8) | −0.0060 (8) | −0.0098 (8) |
C17 | 0.0309 (9) | 0.0252 (10) | 0.0256 (9) | −0.0040 (7) | 0.0025 (7) | −0.0101 (7) |
C18 | 0.0313 (9) | 0.0289 (11) | 0.0292 (10) | −0.0036 (8) | 0.0001 (7) | −0.0103 (8) |
C19 | 0.0312 (10) | 0.0342 (11) | 0.0302 (10) | −0.0073 (8) | 0.0014 (7) | −0.0086 (8) |
C20 | 0.0329 (10) | 0.0320 (10) | 0.0276 (9) | 0.0022 (8) | −0.0036 (7) | −0.0125 (8) |
C21 | 0.0351 (11) | 0.0438 (13) | 0.0311 (10) | −0.0036 (9) | −0.0056 (8) | −0.0067 (9) |
C22 | 0.0612 (15) | 0.0515 (15) | 0.0581 (14) | −0.0118 (11) | −0.0262 (11) | −0.0167 (11) |
O1—C6 | 1.2258 (19) | C5—H5 | 0.9300 |
O2—C8 | 1.356 (2) | C7—C8 | 1.430 (2) |
O2—C11 | 1.398 (2) | C7—H7 | 0.9300 |
O3—C17 | 1.2325 (19) | C8—C9 | 1.347 (2) |
O4—C19 | 1.350 (2) | C9—C10 | 1.396 (2) |
O4—C22 | 1.388 (3) | C9—H9 | 0.9300 |
N1—C1 | 1.337 (2) | C10—C11 | 1.333 (3) |
N1—C5 | 1.338 (2) | C10—H10 | 0.9300 |
N2—C6 | 1.351 (2) | C11—H11 | 0.9300 |
N2—N3 | 1.381 (2) | C12—C13 | 1.377 (3) |
N2—H2N | 0.893 (14) | C12—H12 | 0.9300 |
N3—C7 | 1.285 (2) | C13—C14 | 1.379 (3) |
N4—C12 | 1.333 (2) | C13—H13 | 0.9300 |
N4—C16 | 1.333 (2) | C14—C15 | 1.387 (2) |
N5—C17 | 1.346 (2) | C14—H14 | 0.9300 |
N5—N6 | 1.383 (2) | C15—C16 | 1.390 (2) |
N5—H5N | 0.858 (15) | C15—C17 | 1.494 (2) |
N6—C18 | 1.279 (2) | C16—H16 | 0.9300 |
C1—C2 | 1.376 (2) | C18—C19 | 1.432 (3) |
C1—H1 | 0.9300 | C18—H18 | 0.9300 |
C2—C3 | 1.371 (2) | C19—C20 | 1.340 (2) |
C2—H2 | 0.9300 | C20—C21 | 1.403 (2) |
C3—C4 | 1.385 (2) | C20—H20 | 0.9300 |
C3—H3 | 0.9300 | C21—C22 | 1.314 (3) |
C4—C5 | 1.391 (2) | C21—H21 | 0.9300 |
C4—C6 | 1.499 (2) | C22—H22 | 0.9300 |
C8—O2—C11 | 105.59 (15) | C11—C10—C9 | 106.90 (17) |
C19—O4—C22 | 105.42 (15) | C11—C10—H10 | 126.6 |
C1—N1—C5 | 117.26 (15) | C9—C10—H10 | 126.6 |
C6—N2—N3 | 119.18 (14) | C10—C11—O2 | 109.84 (16) |
C6—N2—H2N | 121.8 (12) | C10—C11—H11 | 125.1 |
N3—N2—H2N | 117.9 (12) | O2—C11—H11 | 125.1 |
C7—N3—N2 | 114.99 (14) | N4—C12—C13 | 124.17 (18) |
C12—N4—C16 | 116.25 (16) | N4—C12—H12 | 117.9 |
C17—N5—N6 | 118.33 (14) | C13—C12—H12 | 117.9 |
C17—N5—H5N | 124.5 (14) | C12—C13—C14 | 118.32 (18) |
N6—N5—H5N | 117.2 (14) | C12—C13—H13 | 120.8 |
C18—N6—N5 | 115.34 (14) | C14—C13—H13 | 120.8 |
N1—C1—C2 | 123.62 (17) | C13—C14—C15 | 119.56 (17) |
N1—C1—H1 | 118.2 | C13—C14—H14 | 120.2 |
C2—C1—H1 | 118.2 | C15—C14—H14 | 120.2 |
C3—C2—C1 | 118.45 (17) | C14—C15—C16 | 116.92 (16) |
C3—C2—H2 | 120.8 | C14—C15—C17 | 118.80 (15) |
C1—C2—H2 | 120.8 | C16—C15—C17 | 124.18 (16) |
C2—C3—C4 | 119.73 (15) | N4—C16—C15 | 124.78 (17) |
C2—C3—H3 | 120.1 | N4—C16—H16 | 117.6 |
C4—C3—H3 | 120.1 | C15—C16—H16 | 117.6 |
C3—C4—C5 | 117.67 (15) | O3—C17—N5 | 122.79 (16) |
C3—C4—C6 | 118.95 (14) | O3—C17—C15 | 119.94 (15) |
C5—C4—C6 | 123.37 (15) | N5—C17—C15 | 117.25 (14) |
N1—C5—C4 | 123.25 (16) | N6—C18—C19 | 121.73 (16) |
N1—C5—H5 | 118.4 | N6—C18—H18 | 119.1 |
C4—C5—H5 | 118.4 | C19—C18—H18 | 119.1 |
O1—C6—N2 | 123.49 (16) | C20—C19—O4 | 109.62 (16) |
O1—C6—C4 | 120.77 (15) | C20—C19—C18 | 130.05 (17) |
N2—C6—C4 | 115.74 (14) | O4—C19—C18 | 120.31 (16) |
N3—C7—C8 | 121.36 (16) | C19—C20—C21 | 107.93 (17) |
N3—C7—H7 | 119.3 | C19—C20—H20 | 126.0 |
C8—C7—H7 | 119.3 | C21—C20—H20 | 126.0 |
C9—C8—O2 | 109.95 (15) | C22—C21—C20 | 106.02 (18) |
C9—C8—C7 | 128.47 (17) | C22—C21—H21 | 127.0 |
O2—C8—C7 | 121.59 (16) | C20—C21—H21 | 127.0 |
C8—C9—C10 | 107.72 (16) | C21—C22—O4 | 111.01 (18) |
C8—C9—H9 | 126.1 | C21—C22—H22 | 124.5 |
C10—C9—H9 | 126.1 | O4—C22—H22 | 124.5 |
C6—N2—N3—C7 | −179.93 (16) | C8—O2—C11—C10 | 0.4 (2) |
C17—N5—N6—C18 | −172.91 (14) | C16—N4—C12—C13 | −0.2 (3) |
C5—N1—C1—C2 | −1.3 (3) | N4—C12—C13—C14 | −0.4 (3) |
N1—C1—C2—C3 | 1.6 (3) | C12—C13—C14—C15 | 0.8 (3) |
C1—C2—C3—C4 | −0.4 (3) | C13—C14—C15—C16 | −0.7 (2) |
C2—C3—C4—C5 | −0.9 (2) | C13—C14—C15—C17 | 176.09 (15) |
C2—C3—C4—C6 | 179.60 (16) | C12—N4—C16—C15 | 0.4 (3) |
C1—N1—C5—C4 | −0.1 (3) | C14—C15—C16—N4 | 0.1 (3) |
C3—C4—C5—N1 | 1.2 (3) | C17—C15—C16—N4 | −176.49 (15) |
C6—C4—C5—N1 | −179.32 (16) | N6—N5—C17—O3 | 0.7 (2) |
N3—N2—C6—O1 | −2.0 (3) | N6—N5—C17—C15 | 178.83 (13) |
N3—N2—C6—C4 | 178.51 (14) | C14—C15—C17—O3 | −12.5 (2) |
C3—C4—C6—O1 | 15.9 (2) | C16—C15—C17—O3 | 163.98 (16) |
C5—C4—C6—O1 | −163.54 (17) | C14—C15—C17—N5 | 169.29 (15) |
C3—C4—C6—N2 | −164.56 (15) | C16—C15—C17—N5 | −14.2 (2) |
C5—C4—C6—N2 | 16.0 (2) | N5—N6—C18—C19 | −177.59 (14) |
N2—N3—C7—C8 | −179.07 (15) | C22—O4—C19—C20 | 1.1 (2) |
C11—O2—C8—C9 | −0.6 (2) | C22—O4—C19—C18 | 179.52 (16) |
C11—O2—C8—C7 | 179.48 (16) | N6—C18—C19—C20 | 178.28 (17) |
N3—C7—C8—C9 | 179.63 (18) | N6—C18—C19—O4 | 0.2 (2) |
N3—C7—C8—O2 | −0.5 (3) | O4—C19—C20—C21 | −0.8 (2) |
O2—C8—C9—C10 | 0.6 (2) | C18—C19—C20—C21 | −179.05 (17) |
C7—C8—C9—C10 | −179.48 (18) | C19—C20—C21—C22 | 0.2 (2) |
C8—C9—C10—C11 | −0.4 (2) | C20—C21—C22—O4 | 0.5 (2) |
C9—C10—C11—O2 | 0.0 (2) | C19—O4—C22—C21 | −1.0 (2) |
Cg1 and Cg2 are the centroids of the O4/C19–C22 and O2/C8–C11 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···N1i | 0.86 (2) | 2.10 (2) | 2.944 (2) | 169 (2) |
N2—H2N···O3 | 0.89 (1) | 2.08 (2) | 2.9017 (19) | 154 (2) |
C21—H21···N3ii | 0.93 | 2.58 | 3.410 (3) | 149 |
C16—H16···N1i | 0.93 | 2.53 | 3.370 (3) | 150 |
C11—H11···O1iii | 0.93 | 2.51 | 3.365 (2) | 153 |
C2—H2···O3iv | 0.93 | 2.49 | 3.116 (2) | 125 |
C10—H10···Cg1v | 0.93 | 2.78 | 3.594 (2) | 146 |
C12—H12···Cg2vi | 0.93 | 2.75 | 3.520 (2) | 141 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y, −z+1; (iv) −x+1, −y, −z+2; (v) −x+2, −y+1, −z+1; (vi) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C11H9N3O2 |
Mr | 215.21 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 9.441 (2), 10.237 (3), 11.023 (2) |
α, β, γ (°) | 75.10 (2), 85.413 (19), 84.11 (2) |
V (Å3) | 1022.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.26 × 0.21 × 0.18 |
Data collection | |
Diffractometer | Bruker P4 |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.975, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9430, 3589, 2702 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.117, 1.09 |
No. of reflections | 3589 |
No. of parameters | 298 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.29 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).
Cg1 and Cg2 are the centroids of the O4/C19–C22 and O2/C8–C11 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···N1i | 0.858 (15) | 2.099 (15) | 2.944 (2) | 168.5 (18) |
N2—H2N···O3 | 0.893 (14) | 2.075 (16) | 2.9017 (19) | 153.5 (16) |
C21—H21···N3ii | 0.93 | 2.58 | 3.410 (3) | 149.3 |
C16—H16···N1i | 0.93 | 2.53 | 3.370 (3) | 150.1 |
C11—H11···O1iii | 0.93 | 2.51 | 3.365 (2) | 152.5 |
C2—H2···O3iv | 0.93 | 2.49 | 3.116 (2) | 125.1 |
C10—H10···Cg1v | 0.93 | 2.78 | 3.594 (2) | 146 |
C12—H12···Cg2vi | 0.93 | 2.75 | 3.520 (2) | 141 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y, −z+1; (iv) −x+1, −y, −z+2; (v) −x+2, −y+1, −z+1; (vi) x, y, z+1. |
Acknowledgements
The authors are thankful to the National Single Crystal X-ray Diffraction Facility, IIT, Bombay, for providing the single-crystal XRD data. KJ is thankful to the UGC, New Delhi, for the award of a Teacher Fellowship.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bakir, M. & Brown, O. (2002). J. Mol. Struct. 609, 129–136. Web of Science CrossRef CAS Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Derivatives of pyridine-3-carbohydrazide and their metal complexes possess pronounced biological activities. They also contain versatile binding properties and the presence of the carbonyl-O atom promotes the the formation of a chelate binding center (Neema & Kurup, 2011). Derivatives of pyridine-3-carbohydrazide and their metal complexes have received considerable attention during the last decade because of their versatile applications in nonlinear optics and molecular sensing (Bakir & Brown, 2002). The present report is an extension of earlier studies in this area (Nancy et al., 2011).
The title compound, (I), crystallizes in triclinic space group P1.There are two independent molecules (Fig. 1) in the asymmetric unit with almost the same bond length and bond angle, and therefore the detailed description can be limited to one of these molecules. The molecule adopts an E configuration with respect to C7═N3 bond and it exists in the keto form with C6═O1 bond length of 1.226 (2) Å which is very close to a formal C═O bond length [1.21 Å] (Allen et al., 1987). The dihedral angle between pyridine and furan rings is 14.96 (10)°. The O1 and N3 atoms are syn with respect to the C6—N2 bond having a torsion angle of -2.0 (3)°. The molecule is almost planar with maximum deviation of 0.265 (2) Å for atom C2; the other molecule has the maximum deviation of 0.212 (1) Å for the atom O3 from its least-squares plane.
Conventional N—H···O,N hydrogen bonds are present, Table 1, Moreover, there are non-conventional intermolecular interactions present in the crystal structure, Table 1, which contribute to the formation of a 3-D network.
Fig. 2 shows a partial packing diagram. The molecules shown participate in C–H···π interactions formed between the H atoms attached at the C10 and C12 atoms and the furan rings, Table 1. The presence of π–π interactions, with centroid-centroid distances of 3.7864 (15), 3.7864 (15), 3.7274 (15) and 3.7273 (15) Å between the rings, is also noted.