
In the title structure, C14H10N4O2, the pyridyl ring is twisted with respect to the central —C(=O)—NH—N= fragment by 17.7 (1)°, whereas the indole fused-ring system is almost coplanar with this fragment. Molecules are linked into a linear chain motif by N—H
O hydrogen bonds.

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006628/lh6376sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006628/lh6376Isup2.hkl |
CCDC reference: 270477
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.
2-Oxo-2,3-dihydro-1H-indol-3-one nicotinoylhydrazone top
Crystal data top
C14H10N4O2 | F(000) = 552 |
Mr = 266.26 | Dx = 1.452 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5073 reflections |
a = 8.9066 (5) Å | θ = 2.3–27.0° |
b = 11.7021 (6) Å | µ = 0.10 mm−1 |
c = 11.7768 (6) Å | T = 295 K |
β = 97.097 (1)° | Block, orange |
V = 1218.0 (1) Å3 | 0.37 × 0.35 × 0.32 mm |
Z = 4 |
Data collection top
Bruker SMART area-detector diffractometer | 2149 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 27.0°, θmin = 2.3° |
φ and ω scans | h = −11→11 |
10102 measured reflections | k = −14→14 |
2643 independent reflections | l = −15→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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | All H-atom parameters refined |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0617P)2 + 0.2785P] where P = (Fo2 + 2Fc2)/3 |
2643 reflections | (Δ/σ)max = 0.001 |
221 parameters | Δρmax = 0.23 e Å−3 |
10 restraints | Δρmin = −0.17 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.6400 (1) | 0.5242 (1) | 0.3530 (1) | 0.0452 (3) | |
O2 | 0.6793 (1) | 0.2888 (1) | 0.7066 (1) | 0.0532 (3) | |
N1 | 1.0048 (2) | 0.7215 (1) | 0.4873 (1) | 0.0575 (4) | |
N2 | 0.6583 (1) | 0.4128 (1) | 0.5109 (1) | 0.0365 (3) | |
N3 | 0.5505 (1) | 0.3394 (1) | 0.4620 (1) | 0.0339 (3) | |
N4 | 0.5054 (2) | 0.1415 (1) | 0.6821 (1) | 0.0446 (3) | |
C1 | 1.0440 (2) | 0.7179 (2) | 0.5999 (2) | 0.0581 (4) | |
C2 | 0.9759 (2) | 0.6494 (1) | 0.6729 (1) | 0.0555 (4) | |
C3 | 0.8609 (2) | 0.5775 (1) | 0.6279 (1) | 0.0478 (4) | |
C4 | 0.8184 (1) | 0.5780 (1) | 0.5108 (1) | 0.0356 (3) | |
C5 | 0.8931 (2) | 0.6521 (1) | 0.4454 (1) | 0.0455 (3) | |
C6 | 0.6978 (1) | 0.5040 (1) | 0.4500 (1) | 0.0336 (3) | |
C7 | 0.5166 (1) | 0.2566 (1) | 0.5265 (1) | 0.0330 (3) | |
C8 | 0.5798 (2) | 0.2338 (1) | 0.6493 (1) | 0.0389 (3) | |
C9 | 0.4027 (2) | 0.0987 (1) | 0.5919 (1) | 0.0372 (3) | |
C10 | 0.3104 (2) | 0.0043 (1) | 0.5897 (1) | 0.0466 (4) | |
C11 | 0.2185 (2) | −0.0191 (1) | 0.4886 (1) | 0.0503 (4) | |
C12 | 0.2214 (2) | 0.0484 (1) | 0.3924 (1) | 0.0503 (4) | |
C13 | 0.3161 (2) | 0.1422 (1) | 0.3943 (1) | 0.0412 (3) | |
C14 | 0.4058 (1) | 0.1679 (1) | 0.4950 (1) | 0.0332 (3) | |
H2n | 0.702 (2) | 0.398 (1) | 0.579 (1) | 0.051 (5)* | |
H4n | 0.530 (2) | 0.108 (1) | 0.746 (1) | 0.063 (5)* | |
H1 | 1.128 (2) | 0.765 (2) | 0.628 (2) | 0.073 (6)* | |
H2 | 1.003 (2) | 0.653 (2) | 0.753 (1) | 0.064 (5)* | |
H3 | 0.810 (2) | 0.531 (1) | 0.678 (1) | 0.061 (5)* | |
H5 | 0.862 (2) | 0.655 (1) | 0.364 (1) | 0.053 (5)* | |
H10 | 0.315 (2) | −0.045 (1) | 0.655 (1) | 0.054 (5)* | |
H11 | 0.157 (2) | −0.086 (1) | 0.485 (2) | 0.061 (5)* | |
H12 | 0.158 (2) | 0.030 (2) | 0.322 (1) | 0.057 (5)* | |
H13 | 0.322 (2) | 0.187 (1) | 0.327 (1) | 0.048 (4)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0581 (6) | 0.0454 (6) | 0.0300 (5) | −0.0122 (5) | −0.0025 (4) | 0.0013 (4) |
O2 | 0.0600 (6) | 0.0562 (6) | 0.0382 (5) | −0.0078 (5) | −0.0146 (5) | 0.0037 (5) |
N1 | 0.0509 (7) | 0.0574 (8) | 0.0629 (9) | −0.0190 (6) | 0.0020 (6) | −0.0029 (7) |
N2 | 0.0399 (6) | 0.0356 (6) | 0.0319 (6) | −0.0049 (5) | −0.0041 (4) | 0.0011 (4) |
N3 | 0.0380 (5) | 0.0321 (5) | 0.0307 (5) | −0.0024 (4) | 0.0002 (4) | −0.0009 (4) |
N4 | 0.0589 (7) | 0.0434 (7) | 0.0293 (6) | −0.0013 (6) | −0.0028 (5) | 0.0079 (5) |
C1 | 0.0478 (9) | 0.0505 (9) | 0.0711 (11) | −0.0111 (7) | −0.0124 (8) | −0.0036 (8) |
C2 | 0.0658 (10) | 0.0462 (8) | 0.0478 (9) | −0.0011 (7) | −0.0193 (7) | −0.0026 (7) |
C3 | 0.0590 (9) | 0.0413 (8) | 0.0405 (8) | −0.0051 (7) | −0.0048 (6) | 0.0007 (6) |
C4 | 0.0358 (6) | 0.0323 (6) | 0.0375 (7) | 0.0004 (5) | 0.0001 (5) | −0.0027 (5) |
C5 | 0.0463 (8) | 0.0464 (8) | 0.0433 (8) | −0.0083 (6) | 0.0038 (6) | −0.0018 (6) |
C6 | 0.0367 (6) | 0.0342 (6) | 0.0298 (6) | −0.0002 (5) | 0.0038 (5) | −0.0024 (5) |
C7 | 0.0380 (6) | 0.0321 (6) | 0.0282 (6) | 0.0026 (5) | 0.0012 (5) | −0.0004 (5) |
C8 | 0.0458 (7) | 0.0385 (7) | 0.0306 (6) | 0.0035 (6) | −0.0022 (5) | 0.0012 (5) |
C9 | 0.0455 (7) | 0.0334 (6) | 0.0328 (6) | 0.0032 (5) | 0.0053 (5) | 0.0009 (5) |
C10 | 0.0599 (9) | 0.0376 (7) | 0.0438 (8) | −0.0030 (6) | 0.0125 (7) | 0.0073 (6) |
C11 | 0.0590 (9) | 0.0385 (7) | 0.0542 (9) | −0.0136 (7) | 0.0105 (7) | −0.0014 (6) |
C12 | 0.0579 (9) | 0.0471 (8) | 0.0441 (8) | −0.0139 (7) | −0.0008 (7) | −0.0041 (6) |
C13 | 0.0503 (8) | 0.0389 (7) | 0.0332 (7) | −0.0064 (6) | 0.0004 (5) | 0.0010 (5) |
C14 | 0.0398 (6) | 0.0300 (6) | 0.0298 (6) | 0.0018 (5) | 0.0038 (5) | 0.0005 (5) |
Geometric parameters (Å, º) top
O1—C6 | 1.217 (2) | C9—C10 | 1.376 (2) |
O2—C8 | 1.228 (2) | C9—C14 | 1.401 (2) |
N1—C1 | 1.329 (2) | C10—C11 | 1.385 (2) |
N1—C5 | 1.331 (2) | C11—C12 | 1.384 (2) |
N2—C6 | 1.357 (2) | C12—C13 | 1.383 (2) |
N2—N3 | 1.362 (1) | C13—C14 | 1.379 (2) |
N3—C7 | 1.289 (2) | N2—H2n | 0.86 (1) |
N4—C8 | 1.348 (2) | N4—H4n | 0.86 (1) |
N4—C9 | 1.406 (2) | C1—H1 | 0.96 (1) |
C1—C2 | 1.370 (3) | C2—H2 | 0.95 (1) |
C2—C3 | 1.380 (2) | C3—H3 | 0.96 (1) |
C3—C4 | 1.384 (2) | C5—H5 | 0.97 (1) |
C4—C5 | 1.384 (2) | C10—H10 | 0.95 (1) |
C4—C6 | 1.492 (2) | C11—H11 | 0.95 (1) |
C7—C8 | 1.510 (2) | C12—H12 | 0.97 (1) |
C7—C14 | 1.449 (2) | C13—H13 | 0.96 (1) |
C1—N1—C5 | 116.3 (1) | C9—C14—C9 | 106.7 (1) |
N3—N2—C6 | 119.2 (1) | C7—C14—C13 | 132.9 (1) |
N2—N3—C7 | 115.4 (1) | C9—C14—C13 | 120.4 (1) |
C8—N4—C9 | 111.5 (1) | C6—N2—H2n | 122 (1) |
N1—C1—C2 | 124.3 (1) | N3—N2—H2n | 118 (1) |
C1—C2—C3 | 118.7 (2) | C8—N4—H4n | 123 (1) |
C2—C3—C4 | 118.6 (2) | C9—N4—H4n | 125 (1) |
C3—C4—C5 | 117.8 (1) | N1—C1—H1 | 116 (1) |
C3—C4—C6 | 124.7 (1) | C2—C1—H1 | 120 (1) |
C5—C4—C6 | 117.6 (1) | C1—C2—H2 | 122 (1) |
N1—C5—C4 | 124.4 (1) | C3—C2—H2 | 120 (1) |
O1—C6—N2 | 122.8 (1) | C2—C3—H3 | 120 (1) |
O1—C6—C4 | 122.3 (1) | C4—C3—H3 | 122 (1) |
N2—C6—C4 | 114.9 (1) | N1—C5—H5 | 117 (1) |
N3—C7—C8 | 127.6 (1) | C4—C5—H5 | 118 (1) |
N3—C7—C14 | 126.1 (1) | C9—C10—H10 | 120 (1) |
C8—C7—C14 | 106.2 (1) | C11—C10—H10 | 122 (1) |
O2—C8—N4 | 127.6 (1) | C12—C11—H11 | 120 (1) |
O2—C8—C7 | 126.3 (1) | C10—C11—H11 | 119 (1) |
N4—C8—C7 | 106.1 (1) | C13—C12—H12 | 119 (1) |
N4—C9—C10 | 129.2 (1) | C11—C12—H12 | 121 (1) |
N4—C9—C14 | 109.4 (1) | C14—C13—H13 | 120 (1) |
C10—C9—C14 | 121.4 (1) | C12—C13—H13 | 121 (1) |
C9—C10—C11 | 117.5 (1) | C13—C12—H12 | 119 (1) |
C10—C11—C12 | 121.5 (1) | C11—C12—H12 | 121 (1) |
C11—C12—C13 | 120.8 (1) | C14—C13—H13 | 120 (1) |
C12—C13—C14 | 118.3 (1) | C12—C13—H13 | 121 (1) |
C6—N2—N3—C7 | −178.2 (1) | C14—C7—C8—O2 | 178.3 (1) |
C5—N1—C1—C2 | −0.8 (3) | N3—C7—C8—N4 | 177.2 (1) |
N1—C1—C2—C3 | 1.2 (3) | C14—C7—C8—N4 | −1.5 (1) |
C1—C2—C3—C4 | −0.4 (2) | C8—N4—C9—C10 | 177.5 (1) |
C2—C3—C4—C5 | −0.7 (2) | C8—N4—C9—C14 | −1.7 (2) |
C2—C3—C4—C6 | 179.1 (1) | C14—C9—C10—C11 | −1.0 (2) |
C1—N1—C5—C4 | −0.5 (2) | N4—C9—C10—C11 | 179.9 (1) |
C3—C4—C5—N1 | 1.2 (2) | C9—C10—C11—C12 | 1.3 (2) |
C6—C4—C5—N1 | −178.6 (1) | C10—C11—C12—C13 | −0.3 (3) |
N3—N2—C6—O1 | 0.6 (2) | C11—C12—C13—C14 | −1.1 (2) |
N3—N2—C6—C4 | −179.2 (1) | C12—C13—C14—C9 | 1.3 (2) |
C3—C4—C6—O1 | 162.8 (1) | C12—C13—C14—C7 | 179.2 (1) |
C5—C4—C6—O1 | −17.4 (2) | C10—C9—C14—C13 | −0.3 (2) |
C3—C4—C6—N2 | −17.4 (2) | N4—C9—C14—C13 | 179.0 (1) |
C5—C4—C6—N2 | 162.5 (1) | C10—C9—C14—C7 | −178.7 (1) |
N2—N3—C7—C14 | 179.8 (1) | N4—C9—C14—C7 | 0.6 (1) |
N2—N3—C7—C8 | 1.3 (2) | N3—C7—C14—C13 | 3.8 (2) |
C9—N4—C8—O2 | −177.8 (1) | C8—C7—C14—C13 | −177.5 (1) |
C9—N4—C8—C7 | 2.0 (2) | N3—C7—C14—C9 | −178.2 (1) |
N3—C7—C8—O2 | −3.0 (2) | C8—C7—C14—C9 | 0.6 (1) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2n···O2 | 0.86 (1) | 2.00 (1) | 2.711 (2) | 139 (2) |
N4—H4n···O1i | 0.86 (1) | 2.15 (1) | 2.941 (2) | 153 (2) |
Symmetry code: (i) x, −y+1/2, z+1/2. |