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The title compound, NH4+·C8H4NO7- consists of a 2,6-dicarboxy-4-nitrophenolate anion and an ammonium cation, both of which possess crystallographic twofold rotation symmetry. All the O atoms of the anion and the H atoms of the cation contribute to hydrogen bonds, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804022135/su6140sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804022135/su6140Isup2.hkl
Contains datablock I

CCDC reference: 1227243

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.059
  • wR factor = 0.197
  • Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C5 .. 9.29 su
Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 10.21 Cell volume su given = 8.00 PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.00 Sigma PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C5 .. 6.19 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C5 PLAT415_ALERT_2_C Short Inter D-H..H-X H1 .. H3 .. 2.10 Ang. PLAT731_ALERT_1_C Bond Calc 0.89(3), Rep 0.892(10) ...... 3.00 su-Rat N1 -H1A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.89(3), Rep 0.892(10) ...... 3.00 su-Rat N1 -H1B 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.89(3), Rep 0.892(10) ...... 3.00 su-Rat N1 -H1B 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.89(3), Rep 0.892(10) ...... 3.00 su-Rat N1 -H1A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.89(3), Rep 0.892(10) ...... 3.00 su-Rat N1 -H1A 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.97(4), Rep 1.966(16) ...... 2.50 su-Rat H1A -O3 1.555 5.555 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.20 Ratio
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C8H4NO7·H4NF(000) = 1008
Mr = 244.16Dx = 1.713 Mg m3
Orthorhombic, IbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2b 2cCell parameters from 872 reflections
a = 7.128 (3) Åθ = 2.3–25.7°
b = 13.460 (3) ŵ = 0.15 mm1
c = 19.731 (5) ÅT = 293 K
V = 1893.1 (8) Å3Block, colourless
Z = 80.35 × 0.28 × 0.25 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1038 independent reflections
Radiation source: fine-focus sealed tube919 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 89
Tmin = 0.948, Tmax = 0.963k = 1617
5300 measured reflectionsl = 2520
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)] = 0.059H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.197 w = 1/[σ2(Fo2) + (0.117P)2 + 2.7596P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
1038 reflectionsΔρmax = 0.55 e Å3
92 parametersΔρmin = 0.52 e Å3
4 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.006 (2)
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
O10.2451 (3)0.02711 (16)0.33143 (12)0.0543 (7)
O20.0823 (4)0.05687 (14)0.42095 (11)0.0543 (7)
O30.00000.25000.43544 (12)0.0404 (7)
O40.0599 (4)0.17740 (19)0.12496 (10)0.0672 (8)
N10.25000.61670 (19)1.00000.0276 (6)
N20.00000.25000.15403 (14)0.0381 (7)
C10.00000.25000.37246 (15)0.0301 (7)
C20.0606 (3)0.16682 (16)0.33094 (12)0.0302 (6)
C30.0631 (3)0.16685 (16)0.26145 (12)0.0318 (6)
H30.10800.11000.23700.080*
C40.00000.25000.22755 (16)0.0314 (7)
C50.1344 (3)0.07804 (14)0.36361 (11)0.0264 (5)
H10.256 (7)0.0345 (11)0.339 (2)0.080*
H1A0.346 (4)0.652 (3)0.9845 (17)0.077 (12)*
H1B0.224 (5)0.572 (2)0.9683 (15)0.081 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0622 (14)0.0403 (12)0.0605 (13)0.0174 (10)0.0020 (10)0.0009 (9)
O20.0784 (16)0.0394 (11)0.0451 (12)0.0127 (10)0.0032 (10)0.0123 (8)
O30.0644 (17)0.0298 (12)0.0271 (11)0.0079 (11)0.0000.000
O40.099 (2)0.0676 (15)0.0347 (12)0.0125 (14)0.0121 (10)0.0110 (10)
N10.0373 (14)0.0247 (13)0.0209 (11)0.0000.0001 (10)0.000
N20.0389 (16)0.0459 (17)0.0296 (15)0.0045 (13)0.0000.000
C10.0359 (16)0.0240 (14)0.0303 (16)0.0050 (12)0.0000.000
C20.0321 (12)0.0243 (11)0.0342 (12)0.0002 (8)0.0017 (8)0.0011 (8)
C30.0309 (11)0.0306 (11)0.0338 (12)0.0023 (9)0.0005 (8)0.0040 (8)
C40.0290 (15)0.0373 (16)0.0278 (15)0.0025 (12)0.0000.000
C50.0320 (11)0.0180 (9)0.0291 (11)0.0017 (8)0.0048 (8)0.0008 (7)
Geometric parameters (Å, º) top
O1—C51.223 (3)N2—C41.451 (4)
O1—H10.846 (10)C1—C21.453 (3)
O2—C51.224 (3)C1—C2i1.453 (3)
O3—C11.243 (4)C2—C31.371 (3)
O4—N21.211 (3)C2—C51.456 (3)
N1—H1A0.892 (10)C3—C41.379 (3)
N1—H1B0.892 (10)C3—H30.9599
N2—O4i1.211 (3)C4—C3i1.379 (3)
C5—O1—H1121 (3)C1—C2—C5119.4 (2)
H1A—N1—H1B106.7 (16)C2—C3—C4118.7 (2)
O4—N2—O4i123.5 (3)C2—C3—H3120.4
O4—N2—C4118.27 (15)C4—C3—H3120.8
O4i—N2—C4118.27 (15)C3i—C4—C3122.0 (3)
O3—C1—C2124.32 (13)C3i—C4—N2119.00 (15)
O3—C1—C2i124.32 (13)C3—C4—N2119.00 (15)
C2—C1—C2i111.4 (3)O1—C5—O2123.0 (2)
C3—C2—C1124.6 (2)O1—C5—C2117.6 (2)
C3—C2—C5115.99 (19)O2—C5—C2119.4 (2)
O3—C1—C2—C3179.16 (16)O4—N2—C4—C3i178.29 (19)
C2i—C1—C2—C30.84 (16)O4i—N2—C4—C3i1.71 (19)
O3—C1—C2—C52.7 (2)O4—N2—C4—C31.71 (19)
C2i—C1—C2—C5177.3 (2)O4i—N2—C4—C3178.29 (19)
C1—C2—C3—C41.6 (3)C3—C2—C5—O123.6 (3)
C5—C2—C3—C4178.20 (17)C1—C2—C5—O1153.2 (2)
C2—C3—C4—C3i0.78 (15)C3—C2—C5—O2155.5 (2)
C2—C3—C4—N2179.22 (15)C1—C2—C5—O227.7 (3)
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O4ii0.85 (1)2.48 (3)3.172 (4)139 (4)
N1—H1B···O2iii0.89 (1)2.21 (2)3.053 (3)158 (3)
N1—H1A···O2iv0.89 (1)2.46 (4)2.948 (3)115 (3)
N1—H1A···O3iv0.89 (1)1.97 (2)2.832 (2)163 (4)
Symmetry codes: (ii) x, y, z+1/2; (iii) x, y+1/2, z+1/2; (iv) x+1/2, y+1/2, z+1/2.
 

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