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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803002435/ac6028sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803002435/ac6028IIsup2.hkl
Contains datablock II

CCDC reference: 206764

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


Yellow Alert 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

Computing details top

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 top
Crystal data top
C10H11N3O4Z = 2
Mr = 237.22F(000) = 248
Triclinic, P1Dx = 1.516 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.8140 (2) ÅCell parameters from 1004 reflections
b = 8.9168 (4) Åθ = 1–25°
c = 12.4943 (6) ŵ = 0.12 mm1
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) Å3
Data collection top
Nonius KappaCCD
diffractometer
1511 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.104
Horizonally mounted graphite crystal monochromatorθmax = 25°, θmin = 2.7°
Detector resolution: 9 pixels mm-1h = 54
φ and ω scans with κ offsetsk = 1010
6740 measured reflectionsl = 1414
1753 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.055 w = 1/[σ2(Fo2) + (0.1004P)2 + 0.0903P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.159(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.25 e Å3
1753 reflectionsΔρmin = 0.28 e Å3
154 parameters
Special details 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 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 (Å2) top
xyzUiso*/Ueq
C10.3792 (4)0.49229 (19)0.13616 (14)0.0261 (5)
H10.25980.48420.06710.031*
C20.3046 (4)0.6031 (2)0.21654 (15)0.0289 (5)
H20.13220.67080.20090.035*
C30.7058 (4)0.5234 (2)0.33620 (15)0.0330 (5)
H30.81920.53320.40640.04*
C40.7998 (4)0.4100 (2)0.26058 (14)0.0289 (5)
H40.97490.34520.27810.035*
C50.6310 (4)0.3932 (2)0.15798 (14)0.0249 (5)
C60.7359 (4)0.2769 (2)0.07343 (14)0.0245 (5)
C70.4268 (4)0.05865 (19)0.16140 (14)0.0248 (4)
C80.5465 (4)0.0410 (2)0.25235 (14)0.0277 (5)
H8A0.70880.00250.26970.033*
H8B0.62040.14340.22710.033*
C90.3276 (4)0.0571 (2)0.35575 (14)0.0290 (5)
H9A0.27080.04310.38640.035*
H9B0.15550.08940.33730.035*
C100.4435 (4)0.1716 (2)0.44035 (14)0.0287 (5)
N10.4647 (3)0.61917 (18)0.31551 (12)0.0317 (4)
N20.5370 (3)0.21225 (16)0.00228 (11)0.0247 (4)
H50.35580.23270.0090.03*
N30.6248 (3)0.11208 (16)0.08232 (11)0.0261 (4)
H60.80740.08390.08420.031*
O10.9919 (2)0.24573 (14)0.06653 (10)0.0297 (4)
O20.1713 (2)0.08798 (15)0.15559 (10)0.0300 (4)
O30.6600 (3)0.25941 (16)0.42301 (11)0.0408 (4)
O40.2780 (3)0.16703 (16)0.53674 (10)0.0391 (4)
H70.34950.23240.58140.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0272 (9)0.0259 (9)0.0252 (9)0.0069 (7)0.0019 (7)0.0013 (7)
C20.0309 (10)0.0253 (9)0.0296 (10)0.0028 (8)0.0045 (8)0.0012 (7)
C30.0340 (11)0.0384 (11)0.0239 (9)0.0045 (9)0.0010 (8)0.0029 (8)
C40.0283 (10)0.0290 (10)0.0272 (10)0.0030 (8)0.0012 (8)0.0004 (8)
C50.0276 (10)0.0236 (9)0.0244 (9)0.0065 (7)0.0054 (7)0.0002 (7)
C60.0236 (10)0.0246 (9)0.0247 (9)0.0030 (7)0.0023 (7)0.0030 (7)
C70.0263 (10)0.0237 (9)0.0240 (9)0.0033 (7)0.0023 (7)0.0032 (7)
C80.0261 (10)0.0294 (10)0.0257 (9)0.0026 (8)0.0028 (7)0.0018 (7)
C90.0277 (10)0.0309 (10)0.0257 (10)0.0012 (7)0.0022 (8)0.0018 (8)
C100.0277 (10)0.0300 (10)0.0262 (10)0.0032 (8)0.0005 (8)0.0002 (8)
N10.0352 (9)0.0301 (9)0.0287 (9)0.0040 (7)0.0062 (7)0.0032 (7)
N20.0236 (8)0.0263 (8)0.0226 (8)0.0025 (6)0.0046 (6)0.0046 (6)
N30.0240 (8)0.0282 (8)0.0239 (8)0.0017 (6)0.0041 (6)0.0050 (6)
O10.0239 (7)0.0349 (8)0.0285 (7)0.0035 (6)0.0046 (5)0.0053 (5)
O20.0231 (7)0.0381 (8)0.0261 (7)0.0019 (6)0.0037 (5)0.0049 (6)
O30.0373 (8)0.0426 (9)0.0322 (8)0.0109 (7)0.0008 (6)0.0081 (6)
O40.0387 (8)0.0439 (9)0.0254 (8)0.0075 (6)0.0013 (6)0.0088 (6)
Geometric parameters (Å, º) top
C1—C21.385 (3)C7—N31.347 (2)
C1—C51.387 (2)C7—C81.506 (2)
C1—H10.95C8—C91.524 (2)
C2—N11.342 (2)C8—H8A0.99
C2—H20.95C8—H8B0.99
C3—N11.333 (2)C9—C101.507 (3)
C3—C41.387 (3)C9—H9A0.99
C3—H30.95C9—H9B0.99
C4—C51.397 (2)C10—O31.204 (2)
C4—H40.95C10—O41.321 (2)
C5—C61.496 (2)N2—N31.390 (2)
C6—O11.237 (2)N2—H50.88
C6—N21.341 (2)N3—H60.88
C7—O21.231 (2)O4—H70.84
C2—C1—C5118.99 (16)C7—C8—H8A109
C2—C1—H1120.5C9—C8—H8A109
C5—C1—H1120.5C7—C8—H8B109
N1—C2—C1122.97 (16)C9—C8—H8B109
N1—C2—H2118.5H8A—C8—H8B107.8
C1—C2—H2118.5C10—C9—C8111.74 (14)
N1—C3—C4123.39 (16)C10—C9—H9A109.3
N1—C3—H3118.3C8—C9—H9A109.3
C4—C3—H3118.3C10—C9—H9B109.3
C3—C4—C5118.48 (17)C8—C9—H9B109.3
C3—C4—H4120.8H9A—C9—H9B107.9
C5—C4—H4120.8O3—C10—O4123.07 (16)
C1—C5—C4118.36 (16)O3—C10—C9124.51 (15)
C1—C5—C6122.28 (15)O4—C10—C9112.42 (14)
C4—C5—C6119.23 (16)C3—N1—C2117.80 (15)
O1—C6—N2121.40 (16)C6—N2—N3118.20 (14)
O1—C6—C5121.95 (15)C6—N2—H5120.9
N2—C6—C5116.59 (15)N3—N2—H5120.9
O2—C7—N3121.07 (16)C7—N3—N2119.21 (15)
O2—C7—C8124.41 (15)C7—N3—H6120.4
N3—C7—C8114.49 (15)N2—N3—H6120.4
C7—C8—C9113.05 (14)C10—O4—H7109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H5···O1i0.881.992.842 (2)162
N3—H6···O2ii0.882.112.906 (2)150
O4—H7···N1iii0.841.842.673 (2)173
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x, y1, z+1.
 

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