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The title compound, C10H11N5O5, contains of di­nitro­phenyl, monooxime and hydrazone groups. The mol­ecules are linked through O—H...N and C—H...O hydrogen bonds. There are also π–π interactions and intramolecular hydrogen bonds. All these hydrogen bonds are highly effective in forming dimeric chains, thereby stabilizing the crystal structure. The monooxime and hydrazone groups both have an E configuration.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015235/rn6016sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015235/rn6016Isup2.hkl
Contains datablock I

CCDC reference: 248774

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.050
  • wR factor = 0.132
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.102 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); 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).

3-[(2,4-Dinitrophenyl)hydrazono]butan-2-one oxime top
Crystal data top
C10H11N5O5F(000) = 584
Mr = 281.24Dx = 1.503 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
a = 10.1400 (16) ÅCell parameters from 8500 reflections
b = 12.3079 (19) Åθ = 2.0–26.8°
c = 10.6624 (18) ŵ = 0.12 mm1
β = 110.950 (12)°T = 293 K
V = 1242.7 (3) Å3Prism, orange
Z = 40.35 × 0.23 × 0.12 mm
Data collection top
Stoe IPDS-2
diffractometer
1207 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.103
Plane graphite monochromatorθmax = 25.0°, θmin = 2.2°
Detector resolution: 6.67 pixels mm-1h = 1211
rotation method scansk = 1414
12323 measured reflectionsl = 1212
2180 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.0738P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.87(Δ/σ)max < 0.001
2180 reflectionsΔρmax = 0.20 e Å3
188 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (4)
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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative 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 large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.0765 (3)0.43607 (17)0.1334 (2)0.0612 (6)
N20.2179 (2)0.20795 (17)0.3256 (2)0.0524 (6)
N30.2115 (3)0.09776 (18)0.3044 (2)0.0546 (6)
N40.1859 (3)0.13339 (19)0.2505 (2)0.0607 (6)
N50.4683 (3)0.2005 (2)0.7159 (3)0.0667 (7)
O10.0878 (2)0.54816 (15)0.1548 (2)0.0796 (7)
H10.03990.57970.08580.119*
O20.1342 (3)0.07263 (17)0.1538 (2)0.0860 (7)
O30.1729 (2)0.23197 (16)0.2397 (2)0.0844 (7)
O40.4565 (3)0.2972 (2)0.6883 (2)0.0889 (7)
O50.5320 (3)0.1659 (2)0.8274 (2)0.0997 (8)
C10.1509 (3)0.3830 (2)0.2396 (3)0.0533 (7)
C20.1439 (3)0.2642 (2)0.2222 (3)0.0525 (7)
C30.2746 (3)0.0255 (2)0.4041 (2)0.0466 (6)
C40.2634 (3)0.0874 (2)0.3819 (2)0.0486 (6)
C50.3275 (3)0.1608 (2)0.4837 (3)0.0530 (7)
H50.32000.23510.46710.064*
C60.4014 (3)0.1221 (2)0.6082 (3)0.0505 (7)
C70.4155 (3)0.0113 (2)0.6347 (3)0.0520 (7)
H70.46770.01310.72080.062*
C80.3534 (3)0.0614 (2)0.5357 (2)0.0488 (6)
H80.36280.13540.55430.059*
C90.2386 (3)0.4336 (2)0.3680 (3)0.0708 (8)
H9A0.29360.49130.35080.106*
H9B0.30060.38000.42440.106*
H9C0.17870.46240.41220.106*
C100.0540 (4)0.2172 (3)0.0902 (3)0.0781 (9)
H10A0.11310.19090.04380.117*
H10B0.00810.27230.03720.117*
H10C0.00080.15830.10490.117*
H30.166 (3)0.071 (2)0.228 (3)0.076 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0708 (17)0.0440 (13)0.0734 (16)0.0067 (11)0.0316 (13)0.0123 (11)
N20.0577 (14)0.0421 (12)0.0579 (13)0.0008 (10)0.0213 (11)0.0034 (10)
N30.0645 (16)0.0453 (13)0.0485 (13)0.0032 (11)0.0136 (11)0.0023 (11)
N40.0660 (16)0.0523 (14)0.0581 (14)0.0037 (12)0.0153 (12)0.0051 (12)
N50.0694 (17)0.0660 (18)0.0627 (16)0.0060 (14)0.0210 (13)0.0178 (14)
O10.0957 (17)0.0458 (12)0.1002 (16)0.0107 (11)0.0387 (14)0.0163 (11)
O20.1177 (19)0.0608 (13)0.0543 (12)0.0020 (12)0.0002 (11)0.0018 (11)
O30.1091 (18)0.0487 (13)0.0802 (14)0.0117 (12)0.0152 (12)0.0117 (11)
O40.1108 (19)0.0557 (14)0.0930 (16)0.0105 (13)0.0275 (14)0.0213 (12)
O50.128 (2)0.0914 (18)0.0556 (14)0.0020 (15)0.0040 (13)0.0168 (13)
C10.0553 (17)0.0516 (15)0.0568 (16)0.0033 (13)0.0245 (13)0.0085 (13)
C20.0597 (18)0.0474 (15)0.0514 (15)0.0015 (13)0.0210 (13)0.0041 (12)
C30.0468 (16)0.0451 (15)0.0498 (14)0.0011 (11)0.0196 (12)0.0013 (12)
C40.0515 (16)0.0432 (15)0.0494 (14)0.0031 (11)0.0161 (12)0.0016 (12)
C50.0548 (16)0.0431 (14)0.0638 (16)0.0015 (13)0.0243 (13)0.0026 (13)
C60.0525 (16)0.0484 (16)0.0515 (15)0.0019 (13)0.0195 (13)0.0080 (12)
C70.0539 (17)0.0545 (17)0.0482 (15)0.0019 (13)0.0190 (13)0.0032 (13)
C80.0524 (16)0.0434 (14)0.0528 (15)0.0025 (13)0.0213 (13)0.0006 (12)
C90.088 (2)0.0558 (18)0.0667 (18)0.0013 (16)0.0247 (16)0.0000 (15)
C100.100 (3)0.0606 (19)0.0606 (18)0.0115 (17)0.0124 (17)0.0031 (15)
Geometric parameters (Å, º) top
N1—C11.292 (3)C3—C41.408 (3)
N1—O11.396 (3)C3—C81.414 (3)
N2—C21.290 (3)C4—C51.382 (4)
N2—N31.373 (3)C5—C61.356 (4)
N3—C31.358 (3)C5—H50.9300
N3—H30.85 (3)C6—C71.390 (4)
N4—O31.221 (3)C7—C81.355 (3)
N4—O21.229 (3)C7—H70.9300
N4—C41.454 (3)C8—H80.9300
N5—O51.210 (3)C9—H9A0.9600
N5—O41.222 (3)C9—H9B0.9600
N5—C61.467 (3)C9—H9C0.9600
O1—H10.8200C10—H10A0.9600
C1—C21.473 (4)C10—H10B0.9600
C1—C91.477 (4)C10—H10C0.9600
C2—C101.492 (4)
C1—N1—O1111.6 (2)C6—C5—C4118.6 (2)
C2—N2—N3114.2 (2)C6—C5—H5120.7
C3—N3—N2122.5 (2)C4—C5—H5120.7
C3—N3—H3116 (2)C5—C6—C7121.6 (2)
N2—N3—H3121 (2)C5—C6—N5118.3 (2)
O3—N4—O2121.7 (2)C7—C6—N5120.1 (3)
O3—N4—C4118.7 (2)C8—C7—C6120.2 (2)
O2—N4—C4119.6 (2)C8—C7—H7119.9
O5—N5—O4123.5 (3)C6—C7—H7119.9
O5—N5—C6118.2 (3)C7—C8—C3120.5 (2)
O4—N5—C6118.3 (3)C7—C8—H8119.8
N1—O1—H1109.5C3—C8—H8119.8
N1—C1—C2113.9 (3)C1—C9—H9A109.5
N1—C1—C9124.7 (2)C1—C9—H9B109.5
C2—C1—C9121.4 (2)H9A—C9—H9B109.5
N2—C2—C1115.9 (2)C1—C9—H9C109.5
N2—C2—C10124.8 (2)H9A—C9—H9C109.5
C1—C2—C10119.3 (3)H9B—C9—H9C109.5
N3—C3—C4121.9 (2)C2—C10—H10A109.5
N3—C3—C8120.9 (2)C2—C10—H10B109.5
C4—C3—C8117.3 (2)H10A—C10—H10B109.5
C5—C4—C3121.7 (2)C2—C10—H10C109.5
C5—C4—N4116.3 (2)H10A—C10—H10C109.5
C3—C4—N4122.0 (2)H10B—C10—H10C109.5
C2—N2—N3—C3175.4 (2)O2—N4—C4—C5175.3 (2)
O1—N1—C1—C2179.47 (19)O3—N4—C4—C3175.5 (2)
O1—N1—C1—C90.6 (4)O2—N4—C4—C33.8 (4)
N3—N2—C2—C1178.4 (2)C3—C4—C5—C60.7 (4)
N3—N2—C2—C101.8 (4)N4—C4—C5—C6179.8 (2)
N1—C1—C2—N2179.3 (2)C4—C5—C6—C70.9 (4)
C9—C1—C2—N20.4 (4)C4—C5—C6—N5179.6 (2)
N1—C1—C2—C100.9 (4)O5—N5—C6—C5178.7 (3)
C9—C1—C2—C10179.8 (3)O4—N5—C6—C51.2 (4)
N2—N3—C3—C4178.0 (2)O5—N5—C6—C71.8 (4)
N2—N3—C3—C81.4 (4)O4—N5—C6—C7178.4 (3)
N3—C3—C4—C5179.9 (2)C5—C6—C7—C80.7 (4)
C8—C3—C4—C50.5 (4)N5—C6—C7—C8179.7 (2)
N3—C3—C4—N41.1 (4)C6—C7—C8—C30.4 (4)
C8—C3—C4—N4179.5 (2)N3—C3—C8—C7179.7 (2)
O3—N4—C4—C55.4 (4)C4—C3—C8—C70.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.822.222.932 (3)146
C7—H7···O4ii0.932.543.230 (4)131
N3—H3···O20.85 (3)1.92 (3)2.587 (3)135 (2)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1/2, z+3/2.
Comparative geometrical parameters (Å, °) in the hydrazone moiety of (I) with those in the related compounds (II),(III) and (IV) top
Bonds(I)(II)(III)(IV)
N3—C31.358 (3)1.356 (2)1.343 (3)1.351 (3)
N2—N31.373 (3)1.3714 (18)1.379 (3)1.367 (3)
N2—C21.290 (3)1.276 (2)1.289 (3)1.286 (3)
C3—N3—N2122.5 (2)116.11 (13)119.1 (2)120.39 (19)
C2—N2—N3114.2 (2)116.83 (14)117.0 (2)116.7 (2)
 

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