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Guanidinium 3,5-dinitro­benzoate, CH6N3+·C7H3N2O6-, determined at 130 K, forms a three-dimensional hydrogen-bonded structure involving all six H atoms of the guanidinium cation with oxygen acceptors of the anion including an offset cyclic R22(8) inter­action with the carboxyl­ate group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002231/ww2074sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002231/ww2074Isup2.hkl
Contains datablock I

CCDC reference: 636834

Key indicators

  • Single-crystal X-ray study
  • T = 130 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.082
  • Data-to-parameter ratio = 9.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C4 - C5 .. 7.22 su
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.80 PLAT230_ALERT_2_C Hirshfeld Test Diff for O31 - N3 .. 5.79 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O32 - N3 .. 5.69 su
0 ALERT level A = In general: serious problem 1 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

guanidinium 3,5-dinitrobenzoate top
Crystal data top
CH6N3+·C7H3N2O6F(000) = 560
Mr = 271.20Dx = 1.649 Mg m3
Monoclinic, P21/nMelting point > 553 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 7.5192 (6) ÅCell parameters from 3607 reflections
b = 19.0605 (14) Åθ = 2.7–25.1°
c = 7.8416 (6) ŵ = 0.14 mm1
β = 103.566 (1)°T = 130 K
V = 1092.50 (15) Å3Block, pale yellow
Z = 40.35 × 0.30 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1753 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.042
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
φ and ω scansh = 88
5679 measured reflectionsk = 1822
1920 independent reflectionsl = 89
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0456P)2 + 0.2176P]
where P = (Fo2 + 2Fc2)/3
1920 reflections(Δ/σ)max = 0.001
196 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O310.82160 (13)0.43515 (5)0.13616 (13)0.0315 (3)
O320.71944 (13)0.33287 (5)0.18591 (14)0.0319 (3)
O510.17732 (12)0.31529 (5)0.41666 (13)0.0290 (3)
O520.06420 (13)0.41025 (5)0.49914 (13)0.0318 (3)
O710.20734 (12)0.63577 (5)0.26166 (13)0.0273 (3)
O720.49504 (13)0.64933 (5)0.24015 (14)0.0297 (3)
N30.71093 (14)0.39680 (6)0.18338 (14)0.0235 (3)
N50.16895 (14)0.37908 (6)0.42697 (14)0.0226 (3)
C10.38744 (16)0.53391 (6)0.26828 (16)0.0198 (4)
C20.53620 (16)0.50218 (7)0.22262 (15)0.0202 (4)
C30.55620 (16)0.43033 (7)0.23768 (16)0.0204 (4)
C40.43766 (16)0.38789 (7)0.30212 (16)0.0206 (3)
C50.29388 (16)0.42152 (7)0.34990 (16)0.0200 (4)
C60.26420 (16)0.49302 (7)0.33223 (15)0.0201 (4)
C70.36069 (16)0.61278 (7)0.25419 (16)0.0214 (4)
N110.32551 (17)0.84271 (6)0.63665 (16)0.0268 (4)
N210.16486 (15)0.75419 (6)0.47043 (16)0.0252 (3)
N310.46675 (16)0.77190 (7)0.47269 (16)0.0255 (4)
C110.31931 (16)0.78941 (6)0.52754 (16)0.0205 (3)
H20.623000.529600.181500.0240*
H40.454200.338500.312900.0250*
H60.161400.513900.363200.0240*
H11A0.430 (2)0.8612 (8)0.678 (2)0.028 (4)*
H11B0.230 (2)0.8484 (8)0.684 (2)0.030 (4)*
H21A0.074 (2)0.7622 (7)0.5162 (19)0.024 (4)*
H21B0.171 (2)0.7161 (9)0.407 (2)0.033 (4)*
H31A0.461 (2)0.7413 (8)0.395 (2)0.029 (4)*
H31B0.560 (2)0.7961 (9)0.507 (2)0.033 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O310.0249 (5)0.0344 (6)0.0403 (6)0.0014 (4)0.0177 (4)0.0035 (4)
O320.0299 (5)0.0238 (5)0.0453 (6)0.0065 (4)0.0155 (4)0.0019 (4)
O510.0272 (5)0.0231 (5)0.0385 (6)0.0033 (4)0.0114 (4)0.0009 (4)
O520.0305 (5)0.0341 (6)0.0372 (6)0.0057 (4)0.0211 (4)0.0045 (4)
O710.0189 (5)0.0244 (5)0.0397 (6)0.0027 (4)0.0090 (4)0.0017 (4)
O720.0234 (5)0.0226 (5)0.0467 (6)0.0003 (4)0.0155 (4)0.0018 (4)
N30.0200 (6)0.0287 (6)0.0225 (6)0.0033 (5)0.0065 (4)0.0003 (4)
N50.0190 (5)0.0267 (6)0.0227 (6)0.0007 (4)0.0062 (4)0.0019 (4)
C10.0176 (6)0.0234 (7)0.0176 (6)0.0003 (5)0.0027 (5)0.0010 (5)
C20.0170 (6)0.0260 (7)0.0178 (6)0.0015 (5)0.0044 (5)0.0007 (5)
C30.0167 (6)0.0267 (7)0.0180 (6)0.0019 (5)0.0046 (5)0.0020 (5)
C40.0211 (6)0.0215 (6)0.0186 (6)0.0010 (5)0.0033 (5)0.0012 (5)
C50.0169 (6)0.0254 (7)0.0178 (6)0.0023 (5)0.0045 (5)0.0004 (5)
C60.0164 (6)0.0259 (7)0.0181 (6)0.0020 (5)0.0043 (5)0.0020 (5)
C70.0193 (6)0.0248 (7)0.0206 (6)0.0004 (5)0.0055 (5)0.0007 (5)
N110.0179 (6)0.0296 (6)0.0341 (7)0.0006 (5)0.0088 (5)0.0071 (5)
N210.0192 (6)0.0270 (6)0.0308 (6)0.0012 (5)0.0090 (5)0.0014 (5)
N310.0200 (6)0.0263 (6)0.0325 (7)0.0025 (5)0.0108 (5)0.0046 (5)
C110.0188 (6)0.0208 (6)0.0221 (6)0.0016 (5)0.0054 (5)0.0048 (5)
Geometric parameters (Å, º) top
O31—N31.2282 (15)N21—H21A0.857 (15)
O32—N31.2201 (15)N31—H31A0.837 (15)
O51—N51.2212 (15)N31—H31B0.830 (16)
O52—N51.2259 (15)C1—C21.3903 (17)
O71—C71.2477 (16)C1—C61.3913 (17)
O72—C71.2531 (16)C1—C71.5173 (18)
N3—C31.4751 (17)C2—C31.3798 (19)
N5—C51.4725 (17)C3—C41.3840 (18)
N11—C111.3220 (17)C4—C51.3821 (18)
N21—C111.3251 (17)C5—C61.3827 (19)
N31—C111.3226 (18)C2—H20.9500
N11—H11B0.889 (16)C4—H40.9500
N11—H11A0.853 (16)C6—H60.9500
N21—H21B0.887 (17)
O31—N3—O32124.24 (11)N3—C3—C2118.87 (11)
O31—N3—C3117.73 (11)C2—C3—C4123.01 (12)
O32—N3—C3118.03 (11)C3—C4—C5116.08 (12)
O51—N5—O52124.18 (11)N5—C5—C4118.12 (12)
O51—N5—C5118.17 (10)C4—C5—C6123.24 (12)
O52—N5—C5117.65 (11)N5—C5—C6118.63 (11)
C11—N11—H11B117.1 (10)C1—C6—C5118.87 (11)
H11A—N11—H11B123.6 (14)O71—C7—O72125.58 (13)
C11—N11—H11A117.0 (10)O72—C7—C1117.48 (11)
H21A—N21—H21B122.2 (14)O71—C7—C1116.92 (11)
C11—N21—H21A119.3 (10)C1—C2—H2120.00
C11—N21—H21B116.6 (10)C3—C2—H2120.00
H31A—N31—H31B121.3 (15)C3—C4—H4122.00
C11—N31—H31B117.6 (11)C5—C4—H4122.00
C11—N31—H31A120.6 (11)C5—C6—H6121.00
C6—C1—C7119.55 (11)C1—C6—H6121.00
C2—C1—C7120.87 (11)N21—C11—N31119.82 (12)
C2—C1—C6119.56 (11)N11—C11—N21120.21 (12)
C1—C2—C3119.20 (11)N11—C11—N31119.96 (12)
N3—C3—C4118.12 (12)
O31—N3—C3—C24.05 (17)C2—C1—C7—O71165.45 (12)
O31—N3—C3—C4175.78 (11)C2—C1—C7—O7216.15 (18)
O32—N3—C3—C2174.96 (11)C6—C1—C7—O7116.31 (17)
O32—N3—C3—C45.21 (17)C6—C1—C7—O72162.10 (12)
O51—N5—C5—C412.86 (17)C1—C2—C3—N3177.97 (11)
O51—N5—C5—C6168.47 (11)C1—C2—C3—C42.21 (19)
O52—N5—C5—C4166.42 (11)N3—C3—C4—C5179.45 (11)
O52—N5—C5—C612.25 (17)C2—C3—C4—C50.72 (18)
C6—C1—C2—C31.57 (18)C3—C4—C5—N5177.18 (11)
C7—C1—C2—C3179.81 (11)C3—C4—C5—C61.43 (18)
C2—C1—C6—C50.44 (18)N5—C5—C6—C1176.59 (11)
C7—C1—C6—C5177.83 (11)C4—C5—C6—C12.01 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11A···O71i0.853 (16)2.035 (15)2.8376 (16)156.6 (14)
N11—H11B···O72ii0.889 (16)1.919 (15)2.7933 (17)167.4 (15)
N21—H21A···O51iii0.857 (15)2.549 (15)3.1979 (15)133.3 (11)
N21—H21B···O710.887 (17)1.966 (17)2.8499 (15)174.2 (15)
N31—H31A···O720.837 (15)2.182 (15)3.0017 (16)166.5 (14)
N31—H31B···O32iv0.830 (16)2.590 (16)3.1371 (16)124.7 (13)
N31—H31B···O71i0.830 (16)2.422 (16)3.0954 (16)138.9 (13)
Symmetry codes: (i) x+1/2, y+3/2, z+1/2; (ii) x1/2, y+3/2, z+1/2; (iii) x, y+1, z+1; (iv) x+3/2, y+1/2, z+1/2.
 

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