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
CCDC reference: 636834
Key indicators
- Single-crystal X-ray study
- T = 130 K
- Mean (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
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+·C7H3N2O6− | F(000) = 560 |
Mr = 271.20 | Dx = 1.649 Mg m−3 |
Monoclinic, P21/n | Melting point > 553 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5192 (6) Å | Cell parameters from 3607 reflections |
b = 19.0605 (14) Å | θ = 2.7–25.1° |
c = 7.8416 (6) Å | µ = 0.14 mm−1 |
β = 103.566 (1)° | T = 130 K |
V = 1092.50 (15) Å3 | Block, pale yellow |
Z = 4 | 0.35 × 0.30 × 0.20 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1753 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.042 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
φ and ω scans | h = −8→8 |
5679 measured reflections | k = −18→22 |
1920 independent reflections | l = −8→9 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H 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 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O31 | 0.82160 (13) | 0.43515 (5) | 0.13616 (13) | 0.0315 (3) | |
O32 | 0.71944 (13) | 0.33287 (5) | 0.18591 (14) | 0.0319 (3) | |
O51 | 0.17732 (12) | 0.31529 (5) | 0.41666 (13) | 0.0290 (3) | |
O52 | 0.06420 (13) | 0.41025 (5) | 0.49914 (13) | 0.0318 (3) | |
O71 | 0.20734 (12) | 0.63577 (5) | 0.26166 (13) | 0.0273 (3) | |
O72 | 0.49504 (13) | 0.64933 (5) | 0.24015 (14) | 0.0297 (3) | |
N3 | 0.71093 (14) | 0.39680 (6) | 0.18338 (14) | 0.0235 (3) | |
N5 | 0.16895 (14) | 0.37908 (6) | 0.42697 (14) | 0.0226 (3) | |
C1 | 0.38744 (16) | 0.53391 (6) | 0.26828 (16) | 0.0198 (4) | |
C2 | 0.53620 (16) | 0.50218 (7) | 0.22262 (15) | 0.0202 (4) | |
C3 | 0.55620 (16) | 0.43033 (7) | 0.23768 (16) | 0.0204 (4) | |
C4 | 0.43766 (16) | 0.38789 (7) | 0.30212 (16) | 0.0206 (3) | |
C5 | 0.29388 (16) | 0.42152 (7) | 0.34990 (16) | 0.0200 (4) | |
C6 | 0.26420 (16) | 0.49302 (7) | 0.33223 (15) | 0.0201 (4) | |
C7 | 0.36069 (16) | 0.61278 (7) | 0.25419 (16) | 0.0214 (4) | |
N11 | 0.32551 (17) | 0.84271 (6) | 0.63665 (16) | 0.0268 (4) | |
N21 | 0.16486 (15) | 0.75419 (6) | 0.47043 (16) | 0.0252 (3) | |
N31 | 0.46675 (16) | 0.77190 (7) | 0.47269 (16) | 0.0255 (4) | |
C11 | 0.31931 (16) | 0.78941 (6) | 0.52754 (16) | 0.0205 (3) | |
H2 | 0.62300 | 0.52960 | 0.18150 | 0.0240* | |
H4 | 0.45420 | 0.33850 | 0.31290 | 0.0250* | |
H6 | 0.16140 | 0.51390 | 0.36320 | 0.0240* | |
H11A | 0.430 (2) | 0.8612 (8) | 0.678 (2) | 0.028 (4)* | |
H11B | 0.230 (2) | 0.8484 (8) | 0.684 (2) | 0.030 (4)* | |
H21A | 0.074 (2) | 0.7622 (7) | 0.5162 (19) | 0.024 (4)* | |
H21B | 0.171 (2) | 0.7161 (9) | 0.407 (2) | 0.033 (4)* | |
H31A | 0.461 (2) | 0.7413 (8) | 0.395 (2) | 0.029 (4)* | |
H31B | 0.560 (2) | 0.7961 (9) | 0.507 (2) | 0.033 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O31 | 0.0249 (5) | 0.0344 (6) | 0.0403 (6) | −0.0014 (4) | 0.0177 (4) | −0.0035 (4) |
O32 | 0.0299 (5) | 0.0238 (5) | 0.0453 (6) | −0.0065 (4) | 0.0155 (4) | 0.0019 (4) |
O51 | 0.0272 (5) | 0.0231 (5) | 0.0385 (6) | 0.0033 (4) | 0.0114 (4) | −0.0009 (4) |
O52 | 0.0305 (5) | 0.0341 (6) | 0.0372 (6) | −0.0057 (4) | 0.0211 (4) | −0.0045 (4) |
O71 | 0.0189 (5) | 0.0244 (5) | 0.0397 (6) | −0.0027 (4) | 0.0090 (4) | 0.0017 (4) |
O72 | 0.0234 (5) | 0.0226 (5) | 0.0467 (6) | 0.0003 (4) | 0.0155 (4) | −0.0018 (4) |
N3 | 0.0200 (6) | 0.0287 (6) | 0.0225 (6) | −0.0033 (5) | 0.0065 (4) | 0.0003 (4) |
N5 | 0.0190 (5) | 0.0267 (6) | 0.0227 (6) | −0.0007 (4) | 0.0062 (4) | −0.0019 (4) |
C1 | 0.0176 (6) | 0.0234 (7) | 0.0176 (6) | −0.0003 (5) | 0.0027 (5) | 0.0010 (5) |
C2 | 0.0170 (6) | 0.0260 (7) | 0.0178 (6) | 0.0015 (5) | 0.0044 (5) | 0.0007 (5) |
C3 | 0.0167 (6) | 0.0267 (7) | 0.0180 (6) | −0.0019 (5) | 0.0046 (5) | 0.0020 (5) |
C4 | 0.0211 (6) | 0.0215 (6) | 0.0186 (6) | −0.0010 (5) | 0.0033 (5) | 0.0012 (5) |
C5 | 0.0169 (6) | 0.0254 (7) | 0.0178 (6) | 0.0023 (5) | 0.0045 (5) | 0.0004 (5) |
C6 | 0.0164 (6) | 0.0259 (7) | 0.0181 (6) | −0.0020 (5) | 0.0043 (5) | 0.0020 (5) |
C7 | 0.0193 (6) | 0.0248 (7) | 0.0206 (6) | −0.0004 (5) | 0.0055 (5) | 0.0007 (5) |
N11 | 0.0179 (6) | 0.0296 (6) | 0.0341 (7) | −0.0006 (5) | 0.0088 (5) | −0.0071 (5) |
N21 | 0.0192 (6) | 0.0270 (6) | 0.0308 (6) | −0.0012 (5) | 0.0090 (5) | −0.0014 (5) |
N31 | 0.0200 (6) | 0.0263 (6) | 0.0325 (7) | −0.0025 (5) | 0.0108 (5) | −0.0046 (5) |
C11 | 0.0188 (6) | 0.0208 (6) | 0.0221 (6) | 0.0016 (5) | 0.0054 (5) | 0.0048 (5) |
Geometric parameters (Å, º) top
O31—N3 | 1.2282 (15) | N21—H21A | 0.857 (15) |
O32—N3 | 1.2201 (15) | N31—H31A | 0.837 (15) |
O51—N5 | 1.2212 (15) | N31—H31B | 0.830 (16) |
O52—N5 | 1.2259 (15) | C1—C2 | 1.3903 (17) |
O71—C7 | 1.2477 (16) | C1—C6 | 1.3913 (17) |
O72—C7 | 1.2531 (16) | C1—C7 | 1.5173 (18) |
N3—C3 | 1.4751 (17) | C2—C3 | 1.3798 (19) |
N5—C5 | 1.4725 (17) | C3—C4 | 1.3840 (18) |
N11—C11 | 1.3220 (17) | C4—C5 | 1.3821 (18) |
N21—C11 | 1.3251 (17) | C5—C6 | 1.3827 (19) |
N31—C11 | 1.3226 (18) | C2—H2 | 0.9500 |
N11—H11B | 0.889 (16) | C4—H4 | 0.9500 |
N11—H11A | 0.853 (16) | C6—H6 | 0.9500 |
N21—H21B | 0.887 (17) | | |
| | | |
O31—N3—O32 | 124.24 (11) | N3—C3—C2 | 118.87 (11) |
O31—N3—C3 | 117.73 (11) | C2—C3—C4 | 123.01 (12) |
O32—N3—C3 | 118.03 (11) | C3—C4—C5 | 116.08 (12) |
O51—N5—O52 | 124.18 (11) | N5—C5—C4 | 118.12 (12) |
O51—N5—C5 | 118.17 (10) | C4—C5—C6 | 123.24 (12) |
O52—N5—C5 | 117.65 (11) | N5—C5—C6 | 118.63 (11) |
C11—N11—H11B | 117.1 (10) | C1—C6—C5 | 118.87 (11) |
H11A—N11—H11B | 123.6 (14) | O71—C7—O72 | 125.58 (13) |
C11—N11—H11A | 117.0 (10) | O72—C7—C1 | 117.48 (11) |
H21A—N21—H21B | 122.2 (14) | O71—C7—C1 | 116.92 (11) |
C11—N21—H21A | 119.3 (10) | C1—C2—H2 | 120.00 |
C11—N21—H21B | 116.6 (10) | C3—C2—H2 | 120.00 |
H31A—N31—H31B | 121.3 (15) | C3—C4—H4 | 122.00 |
C11—N31—H31B | 117.6 (11) | C5—C4—H4 | 122.00 |
C11—N31—H31A | 120.6 (11) | C5—C6—H6 | 121.00 |
C6—C1—C7 | 119.55 (11) | C1—C6—H6 | 121.00 |
C2—C1—C7 | 120.87 (11) | N21—C11—N31 | 119.82 (12) |
C2—C1—C6 | 119.56 (11) | N11—C11—N21 | 120.21 (12) |
C1—C2—C3 | 119.20 (11) | N11—C11—N31 | 119.96 (12) |
N3—C3—C4 | 118.12 (12) | | |
| | | |
O31—N3—C3—C2 | 4.05 (17) | C2—C1—C7—O71 | 165.45 (12) |
O31—N3—C3—C4 | −175.78 (11) | C2—C1—C7—O72 | −16.15 (18) |
O32—N3—C3—C2 | −174.96 (11) | C6—C1—C7—O71 | −16.31 (17) |
O32—N3—C3—C4 | 5.21 (17) | C6—C1—C7—O72 | 162.10 (12) |
O51—N5—C5—C4 | −12.86 (17) | C1—C2—C3—N3 | 177.97 (11) |
O51—N5—C5—C6 | 168.47 (11) | C1—C2—C3—C4 | −2.21 (19) |
O52—N5—C5—C4 | 166.42 (11) | N3—C3—C4—C5 | −179.45 (11) |
O52—N5—C5—C6 | −12.25 (17) | C2—C3—C4—C5 | 0.72 (18) |
C6—C1—C2—C3 | 1.57 (18) | C3—C4—C5—N5 | −177.18 (11) |
C7—C1—C2—C3 | 179.81 (11) | C3—C4—C5—C6 | 1.43 (18) |
C2—C1—C6—C5 | 0.44 (18) | N5—C5—C6—C1 | 176.59 (11) |
C7—C1—C6—C5 | −177.83 (11) | C4—C5—C6—C1 | −2.01 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11A···O71i | 0.853 (16) | 2.035 (15) | 2.8376 (16) | 156.6 (14) |
N11—H11B···O72ii | 0.889 (16) | 1.919 (15) | 2.7933 (17) | 167.4 (15) |
N21—H21A···O51iii | 0.857 (15) | 2.549 (15) | 3.1979 (15) | 133.3 (11) |
N21—H21B···O71 | 0.887 (17) | 1.966 (17) | 2.8499 (15) | 174.2 (15) |
N31—H31A···O72 | 0.837 (15) | 2.182 (15) | 3.0017 (16) | 166.5 (14) |
N31—H31B···O32iv | 0.830 (16) | 2.590 (16) | 3.1371 (16) | 124.7 (13) |
N31—H31B···O71i | 0.830 (16) | 2.422 (16) | 3.0954 (16) | 138.9 (13) |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x−1/2, −y+3/2, z+1/2; (iii) −x, −y+1, −z+1; (iv) −x+3/2, y+1/2, −z+1/2. |