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In the title salt, C4H14N22+·2C6H3N2O5-, the dication acts as a hydrogen donor with all its N-H bonds involved in hydrogen bonds to the O atoms of the phenolate and nitro groups, and with six of its eight C-H bonds involved in interactions with the O atoms of the nitro groups of the surrounding 2,4-di­nitro­phenolates. The packing structure is stabilized by these hydrogen-bonding interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021845/na6126sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021845/na6126Isup2.hkl
Contains datablock I

CCDC reference: 180775

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.058
  • wR factor = 0.138
  • Data-to-parameter ratio = 11.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_353 Alert C Long N-H Bond (0.87A) N(6) - H(6) = 1.01 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

(I) top
Crystal data top
C4H14N2+·2C6H3N2O5F(000) = 952
Mr = 456.38Dx = 1.527 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.3777 (3) ÅCell parameters from 3306 reflections
b = 7.3596 (2) Åθ = 2.9–28.3°
c = 22.0064 (1) ŵ = 0.13 mm1
β = 97.886 (2)°T = 183 K
V = 1985.71 (7) Å3Block, yellow
Z = 40.28 × 0.28 × 0.10 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3427 independent reflections
Radiation source: fine-focus sealed tube1790 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.093
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.9°
ω scansh = 1414
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 88
Tmin = 0.965, Tmax = 0.987l = 2617
9040 measured 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)] = 0.058H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0449P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.87(Δ/σ)max < 0.001
3427 reflectionsΔρmax = 0.25 e Å3
304 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0120 (13)
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
O10.8426 (2)0.4659 (4)0.67139 (12)0.0607 (9)
O20.9524 (2)0.6303 (4)0.62746 (12)0.0544 (8)
O30.9231 (2)0.6909 (4)0.41268 (12)0.0520 (8)
O40.79282 (19)0.5594 (4)0.35321 (11)0.0450 (8)
O50.64990 (19)0.3831 (4)0.60616 (10)0.0422 (7)
O60.35296 (19)0.1963 (4)0.31157 (11)0.0511 (8)
O70.46995 (19)0.2267 (4)0.39199 (11)0.0476 (8)
O80.3867 (3)0.1096 (4)0.59010 (12)0.0696 (10)
O90.2509 (3)0.0628 (5)0.60299 (13)0.0723 (11)
O100.17025 (16)0.0135 (3)0.31847 (9)0.0247 (6)
N10.8697 (3)0.5352 (4)0.62518 (14)0.0365 (8)
N20.8393 (2)0.5987 (4)0.40519 (13)0.0342 (8)
N30.3792 (2)0.1771 (4)0.36686 (13)0.0275 (7)
N40.3044 (3)0.0233 (5)0.56998 (15)0.0470 (9)
N50.6660 (2)0.2549 (4)0.71889 (13)0.0290 (7)
H5B0.68250.32810.68530.035*
H5A0.682 (3)0.325 (5)0.7566 (16)0.047 (11)*
H5C0.711 (3)0.148 (6)0.7220 (16)0.055 (12)*
N60.4632 (2)0.4872 (4)0.75961 (12)0.0343 (8)
H60.535 (3)0.489 (5)0.7877 (18)0.068 (13)*
C10.8053 (3)0.5052 (5)0.56617 (14)0.0242 (8)
C20.8505 (3)0.5606 (4)0.51506 (15)0.0257 (8)
H20.91890.61520.51960.031*
C30.7940 (3)0.5347 (4)0.45791 (14)0.0240 (8)
C40.6896 (3)0.4571 (4)0.45037 (14)0.0239 (8)
H40.65200.43850.41130.029*
C50.6440 (3)0.4094 (5)0.50055 (14)0.0265 (8)
H50.57370.36190.49480.032*
C60.6979 (3)0.4284 (5)0.56168 (15)0.0268 (8)
C70.3052 (3)0.0949 (4)0.40386 (14)0.0217 (8)
C80.3371 (3)0.0940 (4)0.46648 (15)0.0268 (8)
H80.40420.14260.48280.032*
C90.2698 (3)0.0215 (5)0.50446 (14)0.0273 (8)
C100.1686 (3)0.0506 (5)0.48069 (15)0.0322 (9)
H100.12300.09900.50690.039*
C110.1368 (3)0.0497 (5)0.41908 (15)0.0277 (8)
H110.06880.09720.40410.033*
C120.2031 (2)0.0207 (4)0.37636 (14)0.0208 (8)
C130.5468 (3)0.2205 (5)0.71083 (15)0.0344 (9)
H13A0.52820.15720.74660.041*
H13B0.52750.14240.67550.041*
C140.4814 (3)0.3925 (5)0.70195 (14)0.0277 (9)
H14A0.51840.47550.67740.033*
H14B0.41100.36430.67880.033*
C150.3853 (3)0.3901 (7)0.79323 (19)0.0720 (16)
H15A0.38320.44780.83220.108*
H15B0.40810.26610.79960.108*
H15C0.31400.39350.76980.108*
C160.4250 (3)0.6776 (6)0.74666 (18)0.0505 (12)
H16A0.47980.74430.72910.076*
H16B0.41190.73470.78420.076*
H16C0.35870.67610.71830.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.072 (2)0.084 (2)0.0219 (16)0.0150 (17)0.0115 (14)0.0012 (15)
O20.0475 (19)0.059 (2)0.0493 (18)0.0120 (15)0.0198 (14)0.0128 (14)
O30.0389 (17)0.063 (2)0.0550 (18)0.0244 (15)0.0087 (13)0.0092 (15)
O40.0360 (16)0.073 (2)0.0246 (15)0.0043 (13)0.0004 (12)0.0107 (13)
O50.0270 (15)0.074 (2)0.0253 (15)0.0087 (13)0.0039 (11)0.0041 (13)
O60.0356 (16)0.090 (2)0.0246 (16)0.0257 (15)0.0056 (12)0.0125 (14)
O70.0317 (16)0.061 (2)0.0456 (17)0.0184 (14)0.0101 (12)0.0038 (14)
O80.100 (3)0.064 (2)0.0346 (18)0.0075 (19)0.0280 (17)0.0052 (15)
O90.075 (2)0.118 (3)0.0262 (17)0.013 (2)0.0142 (15)0.0082 (17)
O100.0220 (13)0.0348 (15)0.0157 (13)0.0025 (10)0.0024 (9)0.0012 (10)
N10.039 (2)0.037 (2)0.030 (2)0.0062 (16)0.0066 (15)0.0108 (16)
N20.0277 (19)0.043 (2)0.032 (2)0.0006 (15)0.0061 (15)0.0100 (15)
N30.0214 (17)0.0283 (18)0.0309 (18)0.0021 (13)0.0034 (14)0.0014 (13)
N40.068 (3)0.047 (2)0.026 (2)0.016 (2)0.0021 (19)0.0002 (17)
N50.0368 (19)0.028 (2)0.0206 (17)0.0089 (15)0.0000 (13)0.0026 (14)
N60.0162 (17)0.069 (3)0.0175 (16)0.0037 (16)0.0014 (13)0.0015 (15)
C10.0259 (19)0.026 (2)0.0189 (19)0.0082 (16)0.0042 (14)0.0061 (15)
C20.0208 (19)0.021 (2)0.033 (2)0.0012 (15)0.0024 (15)0.0021 (16)
C30.0219 (19)0.026 (2)0.0239 (19)0.0019 (15)0.0028 (15)0.0025 (15)
C40.0231 (19)0.027 (2)0.0197 (19)0.0012 (15)0.0046 (14)0.0037 (15)
C50.0204 (19)0.038 (2)0.020 (2)0.0005 (16)0.0021 (15)0.0023 (15)
C60.024 (2)0.035 (2)0.023 (2)0.0095 (16)0.0065 (16)0.0011 (16)
C70.0221 (19)0.019 (2)0.0227 (19)0.0005 (15)0.0013 (14)0.0013 (14)
C80.029 (2)0.022 (2)0.026 (2)0.0034 (16)0.0071 (16)0.0076 (15)
C90.036 (2)0.028 (2)0.0166 (19)0.0056 (17)0.0009 (16)0.0022 (16)
C100.039 (2)0.037 (2)0.023 (2)0.0047 (18)0.0113 (16)0.0047 (17)
C110.024 (2)0.030 (2)0.030 (2)0.0040 (16)0.0046 (15)0.0006 (16)
C120.0213 (18)0.016 (2)0.025 (2)0.0022 (14)0.0020 (15)0.0021 (14)
C130.037 (2)0.035 (2)0.027 (2)0.0004 (18)0.0112 (16)0.0023 (17)
C140.029 (2)0.035 (2)0.0166 (18)0.0005 (17)0.0049 (15)0.0055 (15)
C150.026 (2)0.138 (5)0.057 (3)0.015 (3)0.023 (2)0.047 (3)
C160.037 (2)0.063 (3)0.054 (3)0.012 (2)0.013 (2)0.017 (2)
Geometric parameters (Å, º) top
O1—N11.225 (4)C3—C41.402 (4)
O2—N11.235 (4)C4—C51.354 (4)
O3—N21.232 (3)C4—H40.9300
O4—N21.242 (3)C5—C61.424 (4)
O5—C61.258 (4)C5—H50.9300
O6—N31.224 (3)C7—C81.380 (4)
O7—N31.237 (3)C7—C121.432 (4)
O8—N41.229 (4)C8—C91.366 (5)
O9—N41.225 (4)C8—H80.9300
O10—C121.284 (3)C9—C101.395 (5)
N1—C11.444 (4)C10—C111.359 (4)
N2—C31.435 (4)C10—H100.9300
N3—C71.440 (4)C11—C121.427 (4)
N4—C91.447 (4)C11—H110.9300
N5—C131.484 (4)C13—C141.500 (4)
N5—H5B0.9599C13—H13A0.9700
N5—H5A0.97 (4)C13—H13B0.9700
N5—H5C0.97 (4)C14—H14A0.9700
N6—C151.477 (5)C14—H14B0.9700
N6—C141.492 (4)C15—H15A0.9600
N6—C161.494 (5)C15—H15B0.9600
N6—H61.01 (4)C15—H15C0.9600
C1—C21.384 (4)C16—H16A0.9600
C1—C61.436 (4)C16—H16B0.9600
C2—C31.366 (4)C16—H16C0.9600
C2—H20.9300
O1—N1—O2121.4 (3)C8—C7—C12122.4 (3)
O1—N1—C1120.2 (3)C8—C7—N3116.7 (3)
O2—N1—C1118.3 (3)C12—C7—N3121.0 (3)
O3—N2—O4121.8 (3)C9—C8—C7119.8 (3)
O3—N2—C3119.2 (3)C9—C8—H8120.1
O4—N2—C3119.0 (3)C7—C8—H8120.1
O6—N3—O7120.8 (3)C8—C9—C10120.7 (3)
O6—N3—C7120.5 (3)C8—C9—N4119.0 (3)
O7—N3—C7118.7 (3)C10—C9—N4120.3 (3)
O9—N4—O8122.8 (4)C11—C10—C9119.6 (3)
O9—N4—C9118.4 (4)C11—C10—H10120.2
O8—N4—C9118.7 (4)C9—C10—H10120.2
C13—N5—H5B108.5C10—C11—C12123.1 (3)
C13—N5—H5A106 (2)C10—C11—H11118.5
H5B—N5—H5A108.8C12—C11—H11118.5
C13—N5—H5C116 (2)O10—C12—C11120.4 (3)
H5B—N5—H5C109.2O10—C12—C7125.2 (3)
H5A—N5—H5C109 (3)C11—C12—C7114.4 (3)
C15—N6—C14112.7 (3)N5—C13—C14112.4 (3)
C15—N6—C16109.7 (3)N5—C13—H13A109.1
C14—N6—C16110.9 (3)C14—C13—H13A109.1
C15—N6—H6106 (2)N5—C13—H13B109.1
C14—N6—H6108 (2)C14—C13—H13B109.1
C16—N6—H6110 (2)H13A—C13—H13B107.9
C2—C1—C6122.2 (3)N6—C14—C13115.2 (3)
C2—C1—N1116.8 (3)N6—C14—H14A108.5
C6—C1—N1120.9 (3)C13—C14—H14A108.5
C3—C2—C1119.7 (3)N6—C14—H14B108.5
C3—C2—H2120.2C13—C14—H14B108.5
C1—C2—H2120.2H14A—C14—H14B107.5
C2—C3—C4120.8 (3)N6—C15—H15A109.5
C2—C3—N2119.4 (3)N6—C15—H15B109.5
C4—C3—N2119.6 (3)H15A—C15—H15B109.5
C5—C4—C3119.3 (3)N6—C15—H15C109.5
C5—C4—H4120.3H15A—C15—H15C109.5
C3—C4—H4120.3H15B—C15—H15C109.5
C4—C5—C6123.4 (3)N6—C16—H16A109.5
C4—C5—H5118.3N6—C16—H16B109.5
C6—C5—H5118.3H16A—C16—H16B109.5
O5—C6—C5119.9 (3)N6—C16—H16C109.5
O5—C6—C1125.6 (3)H16A—C16—H16C109.5
C5—C6—C1114.4 (3)H16B—C16—H16C109.5
O1—N1—C1—C2169.0 (3)O6—N3—C7—C125.1 (5)
O2—N1—C1—C210.2 (5)O7—N3—C7—C12174.5 (3)
O1—N1—C1—C613.5 (5)C12—C7—C8—C90.5 (5)
O2—N1—C1—C6167.2 (3)N3—C7—C8—C9178.7 (3)
C6—C1—C2—C33.1 (5)C7—C8—C9—C100.5 (5)
N1—C1—C2—C3179.5 (3)C7—C8—C9—N4179.5 (3)
C1—C2—C3—C41.7 (5)O9—N4—C9—C8170.4 (3)
C1—C2—C3—N2177.6 (3)O8—N4—C9—C88.9 (5)
O3—N2—C3—C26.9 (5)O9—N4—C9—C1010.6 (5)
O4—N2—C3—C2173.1 (3)O8—N4—C9—C10170.1 (3)
O3—N2—C3—C4169.1 (3)C8—C9—C10—C110.4 (5)
O4—N2—C3—C410.9 (5)N4—C9—C10—C11179.4 (3)
C2—C3—C4—C50.8 (5)C9—C10—C11—C120.6 (5)
N2—C3—C4—C5175.1 (3)C10—C11—C12—O10178.1 (3)
C3—C4—C5—C62.1 (5)C10—C11—C12—C71.5 (5)
C4—C5—C6—O5179.2 (3)C8—C7—C12—O10178.1 (3)
C4—C5—C6—C10.8 (5)N3—C7—C12—O102.7 (5)
C2—C1—C6—O5176.5 (3)C8—C7—C12—C111.4 (4)
N1—C1—C6—O50.9 (5)N3—C7—C12—C11177.7 (3)
C2—C1—C6—C51.8 (5)C15—N6—C14—C1371.9 (4)
N1—C1—C6—C5179.1 (3)C16—N6—C14—C13164.7 (3)
O6—N3—C7—C8174.1 (3)N5—C13—C14—N684.6 (4)
O7—N3—C7—C86.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O6i0.97 (4)2.29 (4)2.889 (4)119 (3)
N5—H5A···O10i0.97 (4)1.83 (4)2.771 (4)162 (3)
N5—H5B···O10.962.282.985 (4)129
N5—H5B···O50.961.782.636 (4)147
N5—H5C···O10ii0.96 (4)2.17 (4)3.024 (3)147 (3)
N6—H6···O10i1.01 (4)1.72 (4)2.708 (3)166 (3)
C11—H11···O3iii0.932.413.249 (5)150
C13—H13B···O80.972.393.195 (5)140
C14—H14A···O50.972.503.163 (4)125
C14—H14B···O4iv0.972.593.462 (4)150
C15—H15A···O9v0.962.333.039 (5)130
C15—H15B···O2vi0.962.413.127 (5)131
C16—H16A···O6iv0.962.413.320 (5)159
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1, y, z+1; (iii) x1, y1, z; (iv) x+1, y+1, z+1; (v) x+1/2, y+1/2, z+3/2; (vi) x+3/2, y1/2, z+3/2.
 

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