2-Oxo-2,3-di­hydro-1H-indol-3-one nicotinoyl­hydrazone

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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.109
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

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Computing details

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

Crystal data

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) Å^3	0.37 × 0.35 × 0.32 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	All H-atom parameters refined
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0617P)^2 + 0.2785P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	0.86 (1)	2.15 (1)	2.941 (2)	153 (2)

Symmetry code: (i) x, −y+1/2, z+1/2.