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The title compound, 2CH6N3+·C6H2N2O42-·3H2O, forms a three-dimensional hydrogen-bonded framework structure involving all six protons of the guanidinium cation as donors to the carboxyl­ate O and hetero N atoms of the anions, as well as to the water mol­ecules of solvation. The anions and one of the water mol­ecules lie on crystallographic twofold rotational axes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031047/fl2044sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031047/fl2044Isup2.hkl
Contains datablock I

CCDC reference: 621308

Key indicators

  • Single-crystal X-ray study
  • T = 130 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.085
  • Data-to-parameter ratio = 9.6

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.65
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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: SAINT (Bruker, 1999); data reduction: SAINT; 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.

Bis(guanidinium) pyrazine-2,3-dicarboxylate trihydrate top
Crystal data top
2CH6N3+·C6H2N2O42·3H2OF(000) = 360
Mr = 340.32Dx = 1.458 Mg m3
Monoclinic, P2/cMelting point: 565 K
Hall symbol: -P 2ycMo Kα radiation, λ = 0.71073 Å
a = 7.7141 (8) ÅCell parameters from 1956 reflections
b = 7.7252 (8) Åθ = 2.6–27.5°
c = 13.0299 (13) ŵ = 0.13 mm1
β = 93.403 (2)°T = 130 K
V = 775.12 (14) Å3Block, colourless
Z = 20.35 × 0.30 × 0.25 mm
Data collection top
Bruker CCD area-detector
diffractometer
1202 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.039
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
φ and ω scansh = 99
3904 measured reflectionsk = 98
1360 independent reflectionsl = 158
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0474P)2 + 0.0086P]
where P = (Fo2 + 2Fc2)/3
1360 reflections(Δ/σ)max < 0.001
141 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.16 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
O210.75174 (12)0.55020 (11)0.10249 (7)0.0209 (3)
O220.80649 (12)0.43969 (12)0.25967 (7)0.0231 (3)
N10.83813 (14)0.86590 (14)0.19627 (8)0.0171 (3)
C20.91909 (16)0.71685 (16)0.22302 (10)0.0154 (4)
C60.91933 (17)1.01324 (18)0.22345 (10)0.0179 (4)
C210.81946 (16)0.55376 (17)0.19303 (11)0.0165 (4)
N1G0.47431 (16)0.94365 (17)0.12223 (9)0.0196 (4)
N2G0.40920 (18)0.69045 (16)0.03843 (10)0.0248 (4)
N3G0.20799 (15)0.90970 (17)0.03598 (9)0.0203 (4)
C1G0.36409 (17)0.84835 (17)0.06520 (10)0.0169 (4)
O1W0.10220 (13)0.26837 (13)0.05415 (9)0.0234 (3)
O2W0.500000.24843 (18)0.250000.0235 (5)
H60.8651.1200.2050.022*
H11G0.4487 (19)1.046 (2)0.1450 (13)0.025 (4)*
H12G0.576 (2)0.9006 (19)0.1406 (12)0.028 (4)*
H21G0.514 (2)0.645 (2)0.0647 (14)0.044 (5)*
H22G0.343 (2)0.634 (2)0.0088 (14)0.037 (5)*
H31G0.1868 (18)1.029 (2)0.0464 (12)0.024 (4)*
H32G0.133 (2)0.843 (2)0.0051 (12)0.024 (4)*
H11W0.125 (3)0.334 (3)0.1038 (18)0.064 (7)*
H12W0.154 (2)0.331 (3)0.0023 (17)0.061 (6)*
H21W0.406 (2)0.324 (3)0.2487 (16)0.057 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O210.0239 (5)0.0202 (6)0.0177 (5)0.0025 (4)0.0056 (4)0.0006 (4)
O220.0263 (6)0.0203 (5)0.0222 (6)0.0044 (4)0.0030 (4)0.0054 (4)
N10.0203 (6)0.0174 (6)0.0135 (6)0.0016 (5)0.0002 (5)0.0004 (5)
C20.0181 (7)0.0181 (7)0.0101 (7)0.0008 (5)0.0014 (5)0.0009 (5)
C60.0236 (7)0.0158 (7)0.0143 (7)0.0026 (6)0.0025 (6)0.0006 (6)
C210.0136 (7)0.0169 (7)0.0188 (7)0.0035 (5)0.0002 (6)0.0008 (6)
N1G0.0186 (7)0.0187 (7)0.0209 (7)0.0021 (5)0.0034 (5)0.0044 (5)
N2G0.0246 (7)0.0212 (7)0.0273 (7)0.0035 (6)0.0086 (6)0.0076 (6)
N3G0.0182 (6)0.0198 (7)0.0224 (7)0.0001 (5)0.0038 (5)0.0021 (5)
C1G0.0192 (7)0.0183 (7)0.0132 (7)0.0002 (6)0.0015 (6)0.0018 (6)
O1W0.0278 (6)0.0222 (6)0.0199 (6)0.0036 (4)0.0004 (5)0.0022 (5)
O2W0.0222 (8)0.0159 (7)0.0323 (9)0.00000.0013 (7)0.0000
Geometric parameters (Å, º) top
O21—C211.2618 (17)N1G—H12G0.872 (15)
O22—C211.2453 (17)N1G—H11G0.871 (16)
O1W—H11W0.83 (2)N2G—H22G0.890 (17)
O1W—H12W0.94 (2)N2G—H21G0.928 (16)
O2W—H21W0.930 (19)N3G—H32G0.857 (15)
O2W—H21Wi0.930 (19)N3G—H31G0.947 (15)
N1—C21.3459 (16)C2—C2ii1.3959 (18)
N1—C61.3368 (17)C2—C211.5150 (18)
N1G—C1G1.3199 (18)C6—C6ii1.3876 (19)
N2G—C1G1.3210 (18)C6—H60.950
N3G—C1G1.3286 (18)
H11W—O1W—H12W100 (2)N1—C2—C21115.10 (11)
H21W—O2W—H21Wi102.3 (18)N1—C2—C2ii121.18 (11)
C2—N1—C6117.19 (11)C2ii—C2—C21123.69 (11)
H11G—N1G—H12G118.1 (14)N1—C6—C6ii121.63 (12)
C1G—N1G—H11G123.1 (10)O22—C21—C2117.98 (12)
C1G—N1G—H12G118.7 (10)O21—C21—O22126.19 (12)
H21G—N2G—H22G121.4 (14)O21—C21—C2115.77 (11)
C1G—N2G—H22G119.1 (10)C6ii—C6—H6120
C1G—N2G—H21G119.3 (10)N1—C6—H6119
C1G—N3G—H31G117.9 (9)N1G—C1G—N3G120.33 (13)
H31G—N3G—H32G122.3 (14)N2G—C1G—N3G120.15 (13)
C1G—N3G—H32G119.7 (11)N1G—C1G—N2G119.52 (13)
C6—N1—C2—C21178.38 (11)C2iii—C2—C21—O2257.13 (10)
C6—N1—C2—C2ii0.1 (2)N1—C2—C2ii—N1ii0.3 (2)
C2—N1—C6—C6ii0.32 (18)N1—C2—C2ii—C21ii178.43 (12)
N1—C2—C21—O2145.86 (16)C21—C2—C2ii—C21ii3.4 (2)
N1—C2—C21—O22131.67 (12)N1—C6—C6ii—N1ii0.5 (2)
C2iii—C2—C21—O21120.47 (11)
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+2, y, z+1/2; (iii) x, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H11W···O22i0.83 (2)2.00 (2)2.8160 (15)167 (2)
O1W—H12W···O21iv0.94 (2)1.83 (2)2.7700 (14)178 (2)
O2W—H21W···O22i0.930 (19)1.865 (18)2.7845 (12)170 (2)
N1G—H11G···O2Wv0.871 (16)2.100 (16)2.8836 (17)149.3 (14)
N1G—H11G···O2Wvi0.871 (16)2.100 (16)2.8836 (17)149.3 (14)
N1G—H12G···N10.872 (15)2.124 (15)2.9743 (17)164.6 (13)
N2G—H21G···O210.928 (16)2.009 (16)2.9310 (17)172.3 (16)
N2G—H22G···O21iv0.890 (17)1.986 (17)2.8458 (16)162.0 (14)
N3G—H31G···O1Wv0.947 (15)1.966 (15)2.9021 (17)169.6 (13)
N3G—H32G···O1Wvii0.857 (15)2.112 (16)2.9434 (16)163.3 (14)
Symmetry codes: (i) x+1, y, z+1/2; (iv) x+1, y+1, z; (v) x, y+1, z; (vi) x+1, y+1, z+1/2; (vii) x, y+1, z.
 

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