organic compounds
Issue contents
Article statistics
Download citation
Supporting information
Download PDF of article
Acta Cryst. (2005). E61, o1345-o1346
https://doi.org/10.1107/S1600536805011025
Access
M. Yu, X. Chen and Z.-L. Jing
The title compound, C14H13N3O3, was prepared using 2-hydroxy-3-methoxybenzaldehyde and 4-pyridinecarboxylic acid hydrazide. In the crystal structure, an intramolecular O—H
N hydrogen bond [HN = 1.83 (2) Å] appears to stabilize the planar conformation of the molecule, while intermolecular N—HN hydrogen bonds [HN = 2.213 (15) Å] link molecules into extended chains along [001].
ReadarticleSimilararticles
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011025/lh6389sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011025/lh6389Isup2.hkl |
CCDC reference: 272016
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean
(C-C) = 0.003 Å - R factor = 0.051
- wR factor = 0.116
- Data-to-parameter ratio = 13.6
(C-C) = 0.003 ÅcheckCIF/PLATON results
No syntax errors foundNo errors found in this datablock
Computing details top
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Crystal data
top
| C14H13N3O3 | F(000) = 568 |
| Mr = 271.27 | Dx = 1.415 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 981 reflections |
| a = 7.671 (2) Å | θ = 2.8–24.1° |
| b = 16.268 (5) Å | µ = 0.10 mm−1 |
| c = 10.884 (3) Å | T = 294 K |
| β = 110.415 (5)° | Block, yellow |
| V = 1273.0 (6) Å3 | 0.22 × 0.18 × 0.16 mm |
| Z = 4 |
Data collection
top
| Bruker SMART CCD diffractometer | 2603 independent reflections |
| Radiation source: fine-focus sealed tube | 1752 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.031 |
| φ and ω scans | θmax = 26.4°, θmin = 2.4° |
| Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −9→9 |
| Tmin = 0.968, Tmax = 0.984 | k = −20→19 |
| 7239 measured reflections | l = −13→6 |
top
| 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)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0434P)2 + 0.295P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max < 0.001 |
| 2603 reflections | Δρmax = 0.17 e Å−3 |
| 191 parameters | Δρmin = −0.15 e Å−3 |
| 2 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0053 (15) |
top
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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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-factorwR and goodness of fit S are based on F2, conventionalR-factors R are based on F, with F set to zero fornegative 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 largeas those based on F, and R- factors based on ALL data will beeven larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
top
| x | y | z | Uiso*/Ueq | ||
| N1 | 0.4075 (3) | 0.76604 (10) | −0.36041 (16) | 0.0475 (5) | |
| N2 | 0.3166 (3) | 0.57485 (10) | −0.02169 (17) | 0.0444 (4) | |
| H2B | 0.345 (3) | 0.6220 (8) | 0.0163 (19) | 0.059 (7)* | |
| N3 | 0.2664 (2) | 0.51253 (10) | 0.04393 (16) | 0.0432 (4) | |
| O1 | 0.2588 (2) | 0.49502 (9) | −0.20190 (15) | 0.0614 (5) | |
| O2 | 0.1252 (2) | 0.36890 (9) | 0.05286 (13) | 0.0483 (4) | |
| H2A | 0.159 (4) | 0.4108 (11) | 0.019 (3) | 0.095 (10)* | |
| O3 | 0.0603 (2) | 0.25187 (9) | 0.19040 (14) | 0.0560 (4) | |
| C1 | 0.3095 (3) | 0.70022 (13) | −0.4187 (2) | 0.0527 (6) | |
| H1 | 0.2589 | 0.6997 | −0.5098 | 0.063* | |
| C2 | 0.2789 (3) | 0.63324 (13) | −0.35195 (19) | 0.0464 (5) | |
| H2 | 0.2117 | 0.5884 | −0.3974 | 0.056* | |
| C3 | 0.3491 (3) | 0.63322 (11) | −0.21653 (18) | 0.0366 (5) | |
| C4 | 0.4543 (3) | 0.70007 (11) | −0.15499 (18) | 0.0394 (5) | |
| H4 | 0.5071 | 0.7020 | −0.0641 | 0.047* | |
| C5 | 0.4802 (3) | 0.76391 (12) | −0.23004 (19) | 0.0443 (5) | |
| H5 | 0.5527 | 0.8082 | −0.1871 | 0.053* | |
| C6 | 0.3049 (3) | 0.56064 (12) | −0.1472 (2) | 0.0417 (5) | |
| C7 | 0.2840 (3) | 0.52416 (12) | 0.1639 (2) | 0.0450 (5) | |
| H7 | 0.3282 | 0.5744 | 0.2034 | 0.054* | |
| C8 | 0.2359 (3) | 0.46003 (12) | 0.23904 (18) | 0.0384 (5) | |
| C9 | 0.1622 (3) | 0.38534 (11) | 0.18143 (17) | 0.0373 (5) | |
| C10 | 0.1283 (3) | 0.32253 (12) | 0.25798 (19) | 0.0404 (5) | |
| C11 | 0.1636 (3) | 0.33519 (13) | 0.38993 (19) | 0.0475 (5) | |
| H11 | 0.1420 | 0.2932 | 0.4409 | 0.057* | |
| C12 | 0.2314 (3) | 0.41044 (14) | 0.4467 (2) | 0.0503 (6) | |
| H12 | 0.2524 | 0.4192 | 0.5351 | 0.060* | |
| C13 | 0.2676 (3) | 0.47197 (13) | 0.3725 (2) | 0.0477 (5) | |
| H13 | 0.3136 | 0.5221 | 0.4114 | 0.057* | |
| C14 | 0.0531 (4) | 0.18086 (14) | 0.2647 (2) | 0.0654 (7) | |
| H14A | 0.1741 | 0.1705 | 0.3283 | 0.098* | |
| H14B | 0.0145 | 0.1344 | 0.2071 | 0.098* | |
| H14C | −0.0342 | 0.1897 | 0.3086 | 0.098* |
Atomic displacement parameters (Å2)
top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0595 (12) | 0.0446 (10) | 0.0399 (10) | −0.0026 (9) | 0.0191 (9) | 0.0030 (8) |
| N2 | 0.0627 (12) | 0.0332 (9) | 0.0438 (10) | −0.0007 (9) | 0.0268 (9) | 0.0036 (8) |
| N3 | 0.0541 (12) | 0.0391 (9) | 0.0417 (10) | 0.0020 (8) | 0.0233 (9) | 0.0071 (8) |
| O1 | 0.0910 (13) | 0.0417 (9) | 0.0557 (10) | −0.0143 (8) | 0.0308 (9) | −0.0067 (7) |
| O2 | 0.0685 (11) | 0.0447 (9) | 0.0316 (8) | −0.0030 (8) | 0.0172 (7) | 0.0012 (6) |
| O3 | 0.0766 (11) | 0.0431 (8) | 0.0425 (9) | −0.0119 (8) | 0.0133 (8) | 0.0070 (7) |
| C1 | 0.0657 (16) | 0.0590 (14) | 0.0314 (11) | −0.0072 (12) | 0.0143 (11) | 0.0005 (10) |
| C2 | 0.0556 (14) | 0.0459 (12) | 0.0381 (11) | −0.0084 (10) | 0.0170 (10) | −0.0053 (9) |
| C3 | 0.0390 (11) | 0.0382 (11) | 0.0358 (10) | 0.0041 (9) | 0.0171 (9) | −0.0004 (8) |
| C4 | 0.0461 (13) | 0.0426 (11) | 0.0299 (9) | 0.0006 (9) | 0.0137 (9) | −0.0015 (9) |
| C5 | 0.0528 (14) | 0.0412 (12) | 0.0415 (12) | −0.0043 (10) | 0.0196 (10) | −0.0042 (9) |
| C6 | 0.0464 (13) | 0.0391 (11) | 0.0418 (12) | 0.0024 (9) | 0.0181 (10) | 0.0033 (9) |
| C7 | 0.0561 (14) | 0.0355 (11) | 0.0466 (12) | 0.0029 (10) | 0.0222 (11) | 0.0005 (9) |
| C8 | 0.0434 (12) | 0.0396 (11) | 0.0353 (10) | 0.0044 (9) | 0.0178 (9) | 0.0016 (8) |
| C9 | 0.0400 (12) | 0.0416 (11) | 0.0307 (10) | 0.0062 (9) | 0.0129 (9) | 0.0024 (8) |
| C10 | 0.0409 (12) | 0.0422 (11) | 0.0363 (10) | 0.0027 (9) | 0.0110 (9) | 0.0051 (9) |
| C11 | 0.0505 (14) | 0.0544 (13) | 0.0391 (12) | 0.0046 (11) | 0.0176 (10) | 0.0110 (10) |
| C12 | 0.0614 (15) | 0.0595 (14) | 0.0322 (11) | 0.0065 (11) | 0.0193 (11) | 0.0011 (10) |
| C13 | 0.0574 (14) | 0.0448 (12) | 0.0413 (12) | 0.0021 (10) | 0.0178 (11) | −0.0041 (10) |
| C14 | 0.086 (2) | 0.0455 (13) | 0.0601 (15) | −0.0081 (13) | 0.0202 (14) | 0.0146 (12) |
top
| N1—C5 | 1.332 (3) | C4—C5 | 1.378 (3) |
| N1—C1 | 1.335 (3) | C4—H4 | 0.9300 |
| N2—C6 | 1.357 (3) | C5—H5 | 0.9300 |
| N2—N3 | 1.370 (2) | C7—C8 | 1.451 (3) |
| N2—H2B | 0.863 (9) | C7—H7 | 0.9300 |
| N3—C7 | 1.279 (2) | C8—C9 | 1.393 (3) |
| O1—C6 | 1.213 (2) | C8—C13 | 1.400 (3) |
| O2—C9 | 1.354 (2) | C9—C10 | 1.399 (3) |
| O2—H2A | 0.859 (10) | C10—C11 | 1.381 (3) |
| O3—C10 | 1.366 (2) | C11—C12 | 1.388 (3) |
| O3—C14 | 1.422 (2) | C11—H11 | 0.9300 |
| C1—C2 | 1.375 (3) | C12—C13 | 1.373 (3) |
| C1—H1 | 0.9300 | C12—H12 | 0.9300 |
| C2—C3 | 1.382 (3) | C13—H13 | 0.9300 |
| C2—H2 | 0.9300 | C14—H14A | 0.9600 |
| C3—C4 | 1.380 (3) | C14—H14B | 0.9600 |
| C3—C6 | 1.502 (3) | C14—H14C | 0.9600 |
| C5—N1—C1 | 116.27 (17) | N3—C7—H7 | 119.6 |
| C6—N2—N3 | 117.82 (17) | C8—C7—H7 | 119.6 |
| C6—N2—H2B | 123.3 (15) | C9—C8—C13 | 118.96 (18) |
| N3—N2—H2B | 118.7 (15) | C9—C8—C7 | 121.08 (17) |
| C7—N3—N2 | 118.28 (17) | C13—C8—C7 | 119.94 (19) |
| C9—O2—H2A | 107.8 (19) | O2—C9—C8 | 122.90 (17) |
| C10—O3—C14 | 117.44 (16) | O2—C9—C10 | 117.12 (17) |
| N1—C1—C2 | 123.81 (19) | C8—C9—C10 | 119.96 (17) |
| N1—C1—H1 | 118.1 | O3—C10—C11 | 125.79 (18) |
| C2—C1—H1 | 118.1 | O3—C10—C9 | 114.16 (17) |
| C1—C2—C3 | 119.28 (19) | C11—C10—C9 | 120.05 (19) |
| C1—C2—H2 | 120.4 | C10—C11—C12 | 120.09 (19) |
| C3—C2—H2 | 120.4 | C10—C11—H11 | 120.0 |
| C4—C3—C2 | 117.51 (18) | C12—C11—H11 | 120.0 |
| C4—C3—C6 | 124.86 (17) | C13—C12—C11 | 120.16 (19) |
| C2—C3—C6 | 117.63 (18) | C13—C12—H12 | 119.9 |
| C5—C4—C3 | 119.13 (18) | C11—C12—H12 | 119.9 |
| C5—C4—H4 | 120.4 | C12—C13—C8 | 120.7 (2) |
| C3—C4—H4 | 120.4 | C12—C13—H13 | 119.6 |
| N1—C5—C4 | 123.93 (19) | C8—C13—H13 | 119.6 |
| N1—C5—H5 | 118.0 | O3—C14—H14A | 109.5 |
| C4—C5—H5 | 118.0 | O3—C14—H14B | 109.5 |
| O1—C6—N2 | 123.33 (18) | H14A—C14—H14B | 109.5 |
| O1—C6—C3 | 121.53 (18) | O3—C14—H14C | 109.5 |
| N2—C6—C3 | 115.12 (17) | H14A—C14—H14C | 109.5 |
| N3—C7—C8 | 120.81 (19) | H14B—C14—H14C | 109.5 |
| C6—N2—N3—C7 | 177.23 (19) | N3—C7—C8—C13 | 175.8 (2) |
| C5—N1—C1—C2 | 1.1 (3) | C13—C8—C9—O2 | 179.23 (18) |
| N1—C1—C2—C3 | 1.3 (3) | C7—C8—C9—O2 | −2.3 (3) |
| C1—C2—C3—C4 | −2.7 (3) | C13—C8—C9—C10 | −2.6 (3) |
| C1—C2—C3—C6 | 177.15 (18) | C7—C8—C9—C10 | 175.86 (18) |
| C2—C3—C4—C5 | 1.7 (3) | C14—O3—C10—C11 | −10.8 (3) |
| C6—C3—C4—C5 | −178.12 (18) | C14—O3—C10—C9 | 169.20 (19) |
| C1—N1—C5—C4 | −2.2 (3) | O2—C9—C10—O3 | −0.2 (3) |
| C3—C4—C5—N1 | 0.8 (3) | C8—C9—C10—O3 | −178.50 (17) |
| N3—N2—C6—O1 | −2.7 (3) | O2—C9—C10—C11 | 179.79 (18) |
| N3—N2—C6—C3 | 175.92 (16) | C8—C9—C10—C11 | 1.5 (3) |
| C4—C3—C6—O1 | −159.1 (2) | O3—C10—C11—C12 | −179.4 (2) |
| C2—C3—C6—O1 | 21.1 (3) | C9—C10—C11—C12 | 0.5 (3) |
| C4—C3—C6—N2 | 22.3 (3) | C10—C11—C12—C13 | −1.5 (3) |
| C2—C3—C6—N2 | −157.51 (19) | C11—C12—C13—C8 | 0.4 (3) |
| N2—N3—C7—C8 | −179.03 (17) | C9—C8—C13—C12 | 1.7 (3) |
| N3—C7—C8—C9 | −2.6 (3) | C7—C8—C13—C12 | −176.8 (2) |
