4-(2-Isonicotinoyl­hydrazino)-4-oxobutanoic acid

The title compound, C₁₀H₁₁N₃O₄, was synthesized by reacting isoniazid with succinic anhydride. The structure reveals an infinite two-dimensional network in the (011) plane, stabilized by intermolecular hydrogen bonds. Three of these hydrogen bonds are symmetrically independent.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.055
• wR factor = 0.159
• Data-to-parameter ratio = 11.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.104


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: COLLECT (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-(2-isonicotinoylhydrazino)-4-oxobutanoic acid

Crystal data

C10H11N3O4	Z = 2
Mr = 237.22	F(000) = 248
Triclinic, P1	Dx = 1.516 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8140 (2) Å	Cell parameters from 1004 reflections
b = 8.9168 (4) Å	θ = 1–25°
c = 12.4943 (6) Å	µ = 0.12 mm^−1
α = 83.797 (2)°	T = 120 K
β = 79.735 (2)°	Needle, light yellow
γ = 81.035 (2)°	0.4 × 0.06 × 0.06 mm
V = 519.51 (4) Å^3

Data collection

Nonius KappaCCD diffractometer	1511 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.104
Horizonally mounted graphite crystal monochromator	θmax = 25°, θmin = 2.7°
Detector resolution: 9 pixels mm^-1	h = −5→4
φ and ω scans with κ offsets	k = −10→10
6740 measured reflections	l = −14→14
1753 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.055	w = 1/[σ^2(Fo^2) + (0.1004P)^2 + 0.0903P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.159	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.25 e Å^−3
1753 reflections	Δρmin = −0.28 e Å^−3
154 parameters

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3792 (4)	0.49229 (19)	−0.13616 (14)	0.0261 (5)
H1	0.2598	0.4842	−0.0671	0.031*
C2	0.3046 (4)	0.6031 (2)	−0.21654 (15)	0.0289 (5)
H2	0.1322	0.6708	−0.2009	0.035*
C3	0.7058 (4)	0.5234 (2)	−0.33620 (15)	0.0330 (5)
H3	0.8192	0.5332	−0.4064	0.04*
C4	0.7998 (4)	0.4100 (2)	−0.26058 (14)	0.0289 (5)
H4	0.9749	0.3452	−0.2781	0.035*
C5	0.6310 (4)	0.3932 (2)	−0.15798 (14)	0.0249 (5)
C6	0.7359 (4)	0.2769 (2)	−0.07343 (14)	0.0245 (5)
C7	0.4268 (4)	0.05865 (19)	0.16140 (14)	0.0248 (4)
C8	0.5465 (4)	−0.0410 (2)	0.25235 (14)	0.0277 (5)
H8A	0.7088	0.0025	0.2697	0.033*
H8B	0.6204	−0.1434	0.2271	0.033*
C9	0.3276 (4)	−0.0571 (2)	0.35575 (14)	0.0290 (5)
H9A	0.2708	0.0431	0.3864	0.035*
H9B	0.1555	−0.0894	0.3373	0.035*
C10	0.4435 (4)	−0.1716 (2)	0.44035 (14)	0.0287 (5)
N1	0.4647 (3)	0.61917 (18)	−0.31551 (12)	0.0317 (4)
N2	0.5370 (3)	0.21225 (16)	−0.00228 (11)	0.0247 (4)
H5	0.3558	0.2327	−0.009	0.03*
N3	0.6248 (3)	0.11208 (16)	0.08232 (11)	0.0261 (4)
H6	0.8074	0.0839	0.0842	0.031*
O1	0.9919 (2)	0.24573 (14)	−0.06653 (10)	0.0297 (4)
O2	0.1713 (2)	0.08798 (15)	0.15559 (10)	0.0300 (4)
O3	0.6600 (3)	−0.25941 (16)	0.42301 (11)	0.0408 (4)
O4	0.2780 (3)	−0.16703 (16)	0.53674 (10)	0.0391 (4)
H7	0.3495	−0.2324	0.5814	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0272 (9)	0.0259 (9)	0.0252 (9)	−0.0069 (7)	−0.0019 (7)	−0.0013 (7)
C2	0.0309 (10)	0.0253 (9)	0.0296 (10)	−0.0028 (8)	−0.0045 (8)	−0.0012 (7)
C3	0.0340 (11)	0.0384 (11)	0.0239 (9)	−0.0045 (9)	−0.0010 (8)	0.0029 (8)
C4	0.0283 (10)	0.0290 (10)	0.0272 (10)	−0.0030 (8)	−0.0012 (8)	−0.0004 (8)
C5	0.0276 (10)	0.0236 (9)	0.0244 (9)	−0.0065 (7)	−0.0054 (7)	−0.0002 (7)
C6	0.0236 (10)	0.0246 (9)	0.0247 (9)	−0.0030 (7)	−0.0023 (7)	−0.0030 (7)
C7	0.0263 (10)	0.0237 (9)	0.0240 (9)	−0.0033 (7)	−0.0023 (7)	−0.0032 (7)
C8	0.0261 (10)	0.0294 (10)	0.0257 (9)	−0.0026 (8)	−0.0028 (7)	0.0018 (7)
C9	0.0277 (10)	0.0309 (10)	0.0257 (10)	−0.0012 (7)	−0.0022 (8)	0.0018 (8)
C10	0.0277 (10)	0.0300 (10)	0.0262 (10)	−0.0032 (8)	−0.0005 (8)	−0.0002 (8)
N1	0.0352 (9)	0.0301 (9)	0.0287 (9)	−0.0040 (7)	−0.0062 (7)	0.0032 (7)
N2	0.0236 (8)	0.0263 (8)	0.0226 (8)	−0.0025 (6)	−0.0046 (6)	0.0046 (6)
N3	0.0240 (8)	0.0282 (8)	0.0239 (8)	−0.0017 (6)	−0.0041 (6)	0.0050 (6)
O1	0.0239 (7)	0.0349 (8)	0.0285 (7)	−0.0035 (6)	−0.0046 (5)	0.0053 (5)
O2	0.0231 (7)	0.0381 (8)	0.0261 (7)	−0.0019 (6)	−0.0037 (5)	0.0049 (6)
O3	0.0373 (8)	0.0426 (9)	0.0322 (8)	0.0109 (7)	0.0008 (6)	0.0081 (6)
O4	0.0387 (8)	0.0439 (9)	0.0254 (8)	0.0075 (6)	0.0013 (6)	0.0088 (6)

Geometric parameters (Å, º)

C1—C2	1.385 (3)	C7—N3	1.347 (2)
C1—C5	1.387 (2)	C7—C8	1.506 (2)
C1—H1	0.95	C8—C9	1.524 (2)
C2—N1	1.342 (2)	C8—H8A	0.99
C2—H2	0.95	C8—H8B	0.99
C3—N1	1.333 (2)	C9—C10	1.507 (3)
C3—C4	1.387 (3)	C9—H9A	0.99
C3—H3	0.95	C9—H9B	0.99
C4—C5	1.397 (2)	C10—O3	1.204 (2)
C4—H4	0.95	C10—O4	1.321 (2)
C5—C6	1.496 (2)	N2—N3	1.390 (2)
C6—O1	1.237 (2)	N2—H5	0.88
C6—N2	1.341 (2)	N3—H6	0.88
C7—O2	1.231 (2)	O4—H7	0.84
C2—C1—C5	118.99 (16)	C7—C8—H8A	109
C2—C1—H1	120.5	C9—C8—H8A	109
C5—C1—H1	120.5	C7—C8—H8B	109
N1—C2—C1	122.97 (16)	C9—C8—H8B	109
N1—C2—H2	118.5	H8A—C8—H8B	107.8
C1—C2—H2	118.5	C10—C9—C8	111.74 (14)
N1—C3—C4	123.39 (16)	C10—C9—H9A	109.3
N1—C3—H3	118.3	C8—C9—H9A	109.3
C4—C3—H3	118.3	C10—C9—H9B	109.3
C3—C4—C5	118.48 (17)	C8—C9—H9B	109.3
C3—C4—H4	120.8	H9A—C9—H9B	107.9
C5—C4—H4	120.8	O3—C10—O4	123.07 (16)
C1—C5—C4	118.36 (16)	O3—C10—C9	124.51 (15)
C1—C5—C6	122.28 (15)	O4—C10—C9	112.42 (14)
C4—C5—C6	119.23 (16)	C3—N1—C2	117.80 (15)
O1—C6—N2	121.40 (16)	C6—N2—N3	118.20 (14)
O1—C6—C5	121.95 (15)	C6—N2—H5	120.9
N2—C6—C5	116.59 (15)	N3—N2—H5	120.9
O2—C7—N3	121.07 (16)	C7—N3—N2	119.21 (15)
O2—C7—C8	124.41 (15)	C7—N3—H6	120.4
N3—C7—C8	114.49 (15)	N2—N3—H6	120.4
C7—C8—C9	113.05 (14)	C10—O4—H7	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H5···O1^i	0.88	1.99	2.842 (2)	162
N3—H6···O2^ii	0.88	2.11	2.906 (2)	150
O4—H7···N1^iii	0.84	1.84	2.673 (2)	173

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x, y−1, z+1.