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The crystal structure of the dihydrate of the 1:1 proton-transfer compound of 3,5-di­nitro­salicylic acid with 2-hydroxy­benz­aldehyde oxime (salicyl­aldoxime), C7H8NO2+·C7H3­N2O7-·2H2O, is a three-dimensional hydrogen-bonded polymer. In this, the oxime-N atom of salicyl­aldoxime is protonated and, together with the adjacent O-H group, gives primary cyclic asymmetric hydrogen-bonding associations with both carboxyl O atoms of the acid. These, together with hydrogen-bonding interactions among all species present, including the two water mol­ecules, give an essentially planar ten-membered ring. Peripheral hydrogen bonding also links the water mol­ecules to carboxyl and nitro-O atoms, giving rise to a three-dimensional polymer structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802019463/tk6085sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802019463/tk6085Isup2.hkl
Contains datablock I

CCDC reference: 200791

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.110
  • Data-to-parameter ratio = 10.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: SHELXTL.

2-hydroxybenzaldehyde oximato 3,5-dinitrosalicylate dihydrate top
Crystal data top
C7H8NO2+·C7H3N2O7·2H2OF(000) = 832
Mr = 401.29Dx = 1.569 Mg m3
Monoclinic, P21/nMelting point = 375.5–379.0 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 7.0077 (4) ÅCell parameters from 9872 reflections
b = 8.5126 (5) Åθ = 2.5–25.0°
c = 28.5138 (15) ŵ = 0.14 mm1
β = 92.979 (1)°T = 295 K
V = 1698.66 (17) Å3Block, yellow
Z = 40.50 × 0.30 × 0.10 mm
Data collection top
Bruker CCD area detector
diffractometer
2898 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.019
Graphite monochromatorθmax = 25.0°, θmin = 1.4°
φ and ω scansh = 88
11631 measured reflectionsk = 1010
2985 independent reflectionsl = 3333
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)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0322P)2 + 0.9115P]
where P = (Fo2 + 2Fc2)/3
S = 1.21(Δ/σ)max = 0.003
2985 reflectionsΔρmax = 0.28 e Å3
286 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0094 (12)
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
C20.4094 (3)0.3432 (2)0.14727 (7)0.0393 (5)
C10.4395 (3)0.2119 (2)0.11773 (7)0.0375 (4)
C60.5034 (3)0.0707 (2)0.13615 (7)0.0406 (5)
H60.52560.01380.11650.049*
C50.5344 (3)0.0558 (3)0.18442 (7)0.0437 (5)
C40.5011 (3)0.1778 (3)0.21449 (7)0.0458 (5)
H40.52090.16490.24680.055*
C30.4379 (3)0.3195 (2)0.19616 (7)0.0426 (5)
C70.4014 (3)0.2292 (2)0.06595 (7)0.0399 (5)
C210.1482 (3)0.6670 (2)0.05643 (7)0.0404 (5)
C110.1598 (3)0.5579 (2)0.09301 (7)0.0394 (5)
C610.1118 (3)0.6053 (3)0.13934 (7)0.0459 (5)
H610.11830.53330.16370.055*
C510.0555 (3)0.7568 (3)0.14891 (8)0.0496 (5)
H510.02440.78780.17960.060*
C410.0454 (3)0.8629 (3)0.11247 (8)0.0514 (6)
H410.00700.96550.11900.062*
C310.0910 (3)0.8200 (3)0.06666 (8)0.0483 (5)
H310.08350.89330.04260.058*
C710.2229 (3)0.3984 (2)0.08581 (7)0.0428 (5)
H710.22380.33430.11220.051*
N50.6063 (3)0.0926 (2)0.20404 (6)0.0584 (5)
N30.4007 (3)0.4440 (2)0.22969 (6)0.0547 (5)
N710.2778 (3)0.3367 (2)0.04655 (6)0.0441 (4)
O20.3589 (2)0.47951 (17)0.12884 (5)0.0490 (4)
O720.3570 (2)0.36587 (17)0.05060 (5)0.0483 (4)
O710.4125 (2)0.11242 (17)0.03982 (5)0.0498 (4)
O520.6598 (3)0.1932 (2)0.17730 (6)0.0825 (7)
O510.6122 (4)0.1095 (2)0.24652 (6)0.0894 (7)
O320.4419 (4)0.4218 (2)0.27105 (6)0.0876 (7)
O310.3273 (4)0.5653 (3)0.21638 (7)0.1005 (8)
O210.1963 (2)0.61659 (18)0.01262 (5)0.0516 (4)
O810.3362 (3)0.18387 (18)0.04619 (6)0.0638 (5)
O1W0.1851 (3)0.8375 (2)0.04966 (7)0.0697 (5)
O2W0.1525 (4)0.7594 (3)0.14186 (7)0.0830 (7)
H210.186 (4)0.695 (4)0.0088 (10)0.082 (9)*
H1A0.278 (5)0.915 (5)0.0482 (13)0.119 (14)*
H1B0.175 (4)0.814 (4)0.0798 (12)0.085 (10)*
H2A0.226 (6)0.670 (5)0.1501 (14)0.132 (15)*
H2B0.137 (6)0.806 (5)0.1658 (14)0.121 (15)*
H20.350 (4)0.451 (4)0.0924 (11)0.092 (9)*
H810.366 (4)0.159 (3)0.0116 (11)0.084 (9)*
H71A0.285 (4)0.388 (3)0.0180 (10)0.069 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0387 (10)0.0397 (11)0.0396 (10)0.0017 (8)0.0041 (8)0.0009 (9)
C10.0393 (10)0.0397 (11)0.0336 (10)0.0012 (8)0.0016 (8)0.0001 (8)
C60.0441 (11)0.0421 (11)0.0353 (10)0.0007 (9)0.0002 (8)0.0015 (8)
C50.0516 (12)0.0432 (11)0.0361 (10)0.0038 (9)0.0003 (9)0.0049 (9)
C40.0538 (12)0.0517 (13)0.0322 (10)0.0006 (10)0.0035 (9)0.0012 (9)
C30.0491 (11)0.0430 (12)0.0362 (10)0.0038 (9)0.0069 (9)0.0048 (9)
C70.0426 (11)0.0390 (11)0.0380 (11)0.0012 (9)0.0003 (8)0.0012 (9)
C210.0430 (11)0.0383 (11)0.0402 (11)0.0001 (9)0.0038 (8)0.0022 (9)
C110.0430 (11)0.0381 (11)0.0370 (10)0.0004 (9)0.0001 (8)0.0009 (8)
C610.0506 (12)0.0468 (12)0.0396 (11)0.0009 (10)0.0027 (9)0.0006 (9)
C510.0489 (12)0.0515 (13)0.0478 (12)0.0014 (10)0.0039 (9)0.0119 (10)
C410.0513 (13)0.0411 (12)0.0620 (14)0.0079 (10)0.0039 (10)0.0103 (11)
C310.0539 (13)0.0394 (12)0.0520 (13)0.0042 (10)0.0057 (10)0.0028 (10)
C710.0562 (12)0.0380 (11)0.0336 (10)0.0014 (9)0.0023 (9)0.0038 (8)
N50.0808 (14)0.0548 (12)0.0390 (10)0.0161 (11)0.0016 (9)0.0042 (9)
N30.0766 (13)0.0508 (12)0.0373 (10)0.0029 (10)0.0086 (9)0.0039 (8)
N710.0619 (11)0.0336 (9)0.0361 (9)0.0064 (8)0.0023 (8)0.0038 (7)
O20.0687 (10)0.0383 (8)0.0401 (8)0.0072 (7)0.0041 (7)0.0001 (6)
O720.0687 (10)0.0390 (8)0.0369 (8)0.0082 (7)0.0022 (7)0.0019 (6)
O710.0739 (10)0.0393 (8)0.0355 (8)0.0080 (7)0.0031 (7)0.0019 (6)
O520.1337 (18)0.0627 (12)0.0502 (10)0.0411 (12)0.0014 (11)0.0012 (9)
O510.153 (2)0.0779 (13)0.0371 (9)0.0385 (13)0.0018 (10)0.0131 (9)
O320.152 (2)0.0735 (13)0.0369 (9)0.0174 (13)0.0039 (11)0.0088 (9)
O310.180 (2)0.0672 (13)0.0544 (11)0.0497 (15)0.0059 (13)0.0082 (10)
O210.0794 (11)0.0396 (8)0.0358 (8)0.0079 (8)0.0020 (7)0.0036 (7)
O810.1100 (15)0.0373 (9)0.0428 (9)0.0220 (9)0.0091 (9)0.0025 (7)
O1W0.1053 (16)0.0551 (11)0.0498 (11)0.0104 (11)0.0141 (10)0.0117 (9)
O2W0.131 (2)0.0639 (13)0.0544 (12)0.0331 (13)0.0092 (12)0.0029 (10)
Geometric parameters (Å, º) top
O2—C21.315 (2)C1—C21.422 (3)
O31—N31.206 (3)C1—C61.377 (3)
O32—N31.214 (2)C2—C31.412 (3)
O51—N51.218 (2)C3—C41.379 (3)
O52—N51.219 (2)C4—C51.374 (3)
O71—C71.247 (2)C5—C61.388 (3)
O72—C71.276 (2)C4—H40.9310
O2—H21.07 (3)C6—H60.9298
O21—C211.347 (2)C11—C711.439 (2)
O81—N711.364 (2)C11—C211.402 (3)
O21—H210.91 (3)C11—C611.405 (3)
O81—H811.02 (3)C21—C311.389 (3)
O1W—H1B0.89 (3)C31—C411.378 (3)
O1W—H1A0.93 (4)C41—C511.381 (3)
O2W—H2B0.80 (4)C51—C611.372 (4)
O2W—H2A0.94 (4)C31—H310.9309
N3—C31.460 (3)C41—H410.9299
N5—C51.461 (3)C51—H510.9290
N71—C711.278 (3)C61—H610.9292
N71—H71A0.92 (3)C71—H710.9298
C1—C71.494 (3)
C2—O2—H2100.9 (18)O71—C7—O72122.93 (18)
C21—O21—H21111.3 (19)O71—C7—C1119.89 (16)
N71—O81—H81104.6 (15)O72—C7—C1117.18 (16)
H1A—O1W—H1B107 (3)C5—C4—H4120.45
H2A—O2W—H2B106 (4)C3—C4—H4120.45
O31—N3—O32120.99 (19)C5—C6—H6120.29
O31—N3—C3120.21 (18)C1—C6—H6120.44
O32—N3—C3118.79 (18)C21—C11—C71123.23 (18)
O52—N5—C5118.64 (17)C61—C11—C71117.50 (18)
O51—N5—C5118.43 (18)C21—C11—C61119.26 (18)
O51—N5—O52122.92 (19)O21—C21—C31123.30 (18)
O81—N71—C71118.38 (17)O21—C21—C11117.22 (16)
C71—N71—H71A125.3 (16)C11—C21—C31119.48 (19)
O81—N71—H71A116.2 (16)C21—C31—C41119.9 (2)
C2—C1—C7118.92 (16)C31—C41—C51121.4 (2)
C2—C1—C6121.03 (18)C41—C51—C61119.4 (2)
C6—C1—C7120.05 (16)C11—C61—C51120.6 (2)
C1—C2—C3117.04 (16)N71—C71—C11126.09 (18)
O2—C2—C3122.81 (16)C21—C31—H31120.03
O2—C2—C1120.14 (18)C41—C31—H31120.12
N3—C3—C2121.45 (16)C31—C41—H41119.29
C2—C3—C4121.69 (17)C51—C41—H41119.28
N3—C3—C4116.86 (18)C61—C51—H51120.35
C3—C4—C5119.10 (19)C41—C51—H51120.27
N5—C5—C4118.75 (18)C11—C61—H61119.65
N5—C5—C6119.47 (19)C51—C61—H61119.74
C4—C5—C6121.8 (2)C11—C71—H71116.94
C1—C6—C5119.27 (19)N71—C71—H71116.97
O32—N3—C3—C46.1 (3)C1—C2—C3—N3176.57 (19)
O32—N3—C3—C2174.2 (2)O2—C2—C3—N34.0 (3)
O31—N3—C3—C4172.6 (2)N3—C3—C4—C5178.7 (2)
O31—N3—C3—C27.1 (3)C2—C3—C4—C51.0 (3)
O52—N5—C5—C69.0 (3)C3—C4—C5—C61.0 (3)
O51—N5—C5—C6171.9 (2)C3—C4—C5—N5178.35 (19)
O52—N5—C5—C4170.3 (2)C4—C5—C6—C10.7 (3)
O51—N5—C5—C48.8 (3)N5—C5—C6—C1178.62 (19)
O81—N71—C71—C11178.9 (2)C61—C11—C21—O21179.74 (18)
C6—C1—C7—O72174.63 (19)C71—C11—C21—C31178.2 (2)
C6—C1—C7—O715.8 (3)C61—C11—C21—C310.5 (3)
C2—C1—C6—C51.5 (3)C71—C11—C21—O211.1 (3)
C2—C1—C7—O71174.41 (19)C21—C11—C71—N711.0 (3)
C2—C1—C7—O725.1 (3)C21—C11—C61—C510.5 (3)
C7—C1—C6—C5178.72 (19)C61—C11—C71—N71177.6 (2)
C7—C1—C2—C3176.90 (19)C71—C11—C61—C51178.2 (2)
C7—C1—C2—O23.7 (3)C11—C21—C31—C410.3 (3)
C6—C1—C2—O2176.10 (19)O21—C21—C31—C41179.52 (19)
C6—C1—C2—C33.3 (3)C21—C31—C41—C510.1 (3)
C1—C2—C3—C43.1 (3)C31—C41—C51—C610.1 (3)
O2—C2—C3—C4176.3 (2)C41—C51—C61—C110.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···O71i0.93 (4)1.95 (4)2.853 (2)164 (3)
O1W—H1B···O2W0.89 (3)1.84 (3)2.733 (3)178 (3)
O2—H2···O721.07 (3)1.40 (3)2.431 (2)161 (3)
O2W—H2A···O20.94 (4)1.98 (4)2.822 (3)148 (3)
O2W—H2A···O310.94 (4)2.17 (4)2.911 (3)134 (3)
O2W—H2B···O32ii0.80 (4)2.15 (4)2.947 (3)173 (4)
O21—H21···O1W0.91 (3)1.68 (3)2.590 (2)176 (3)
N71—H71A···O210.92 (3)2.05 (3)2.645 (2)121 (2)
N71—H71A···O720.92 (3)2.00 (3)2.808 (2)145 (2)
O81—H81···O711.02 (3)1.54 (3)2.556 (2)177 (2)
O81—H81···O721.02 (3)2.50 (3)3.162 (2)121.9 (18)
C71—H71···O52iii0.932.393.280 (3)160
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y, z.
 

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