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Tartronic acid forms the title salt, C3H5N2+·C3H3O5-, with imidazole. Hydro­gen bonds in the crystal link the anions, forming a hydrogen-bonded layer. The cations cross-link the layers, leading to a three-dimensional hydrogen-bonded network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024723/bt6367sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024723/bt6367Isup2.hkl
Contains datablock I

CCDC reference: 227783

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.065
  • wR factor = 0.120
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.135 Value of mu given = 0.130 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997–1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN for Windows; molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows.

(I) top
Crystal data top
C3H5N2+·C3H3O5F(000) = 392.00
Mr = 188.14Dx = 1.525 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yabCell parameters from 25 reflections
a = 8.5516 (15) Åθ = 11.1–11.5°
b = 10.2077 (17) ŵ = 0.13 mm1
c = 9.392 (3) ÅT = 298 K
β = 91.64 (2)°Prismatic, colorless
V = 819.6 (3) Å30.50 × 0.40 × 0.35 mm
Z = 4
Data collection top
Rigaku AFC-5R
diffractometer
2032 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.021
Graphite monochromatorθmax = 31.0°, θmin = 2.2°
ω–2θ scansh = 212
Absorption correction: ψ scan
(North et al., 1968)
k = 1414
Tmin = 0.88, Tmax = 0.95l = 1313
6785 measured reflections3 standard reflections every 97 reflections
2617 independent reflections intensity decay: 4.2%
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.065Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00181|Fo|2]
wR(F2) = 0.120(Δ/σ)max = 0.001
S = 1.01Δρmax = 0.36 e Å3
2617 reflectionsΔρmin = 0.27 e Å3
151 parametersExtinction correction: Zachariasen (1967), equ(3) Acta Cryst.(1968) 24, p. 213.
0 restraintsExtinction coefficient: 1.43E-5 (12)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.59735 (10)0.28719 (8)0.24917 (9)0.0351 (2)
O20.43495 (10)0.06705 (8)0.21603 (8)0.0364 (2)
O30.34469 (10)0.12441 (7)0.00186 (7)0.03182 (19)
O40.31606 (10)0.41559 (8)0.00493 (7)0.0355 (2)
O50.34176 (11)0.43865 (8)0.23900 (8)0.0378 (2)
N10.37412 (14)0.34483 (11)0.50833 (10)0.0396 (3)
N20.35097 (14)0.31784 (11)0.73300 (10)0.0397 (3)
C10.34872 (16)0.40520 (12)0.62979 (12)0.0388 (3)
C20.3781 (3)0.19715 (14)0.67617 (14)0.0563 (4)
C30.3926 (2)0.21421 (13)0.53549 (14)0.0547 (4)
C40.50116 (11)0.27806 (9)0.12526 (10)0.0243 (2)
C50.42193 (11)0.14398 (9)0.11786 (10)0.0244 (2)
C60.37693 (11)0.38707 (9)0.12497 (9)0.0236 (2)
H10.378 (2)0.3793 (17)0.4202 (16)0.059 (5)*
H20.329 (2)0.4929 (18)0.6482 (14)0.054 (5)*
H30.335 (2)0.333 (2)0.8282 (19)0.072 (5)*
H40.380 (3)0.116 (2)0.7324 (19)0.081 (6)*
H50.414 (2)0.1576 (18)0.4577 (17)0.063 (5)*
H60.5608 (16)0.2867 (13)0.0383 (14)0.029 (3)*
H70.616 (2)0.208 (2)0.2794 (19)0.074 (6)*
H80.300 (2)0.0466 (17)0.0009 (15)0.052 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0334 (4)0.0333 (4)0.0377 (4)0.0012 (3)0.0137 (3)0.0020 (3)
O20.0468 (5)0.0279 (4)0.0341 (4)0.0025 (3)0.0050 (3)0.0071 (3)
O30.0440 (5)0.0261 (4)0.0251 (3)0.0073 (3)0.0032 (3)0.0019 (3)
O40.0534 (5)0.0317 (4)0.0210 (3)0.0143 (3)0.0066 (3)0.0006 (3)
O50.0505 (5)0.0414 (4)0.0217 (3)0.0169 (4)0.0002 (3)0.0024 (3)
N10.0550 (6)0.0413 (5)0.0224 (4)0.0055 (5)0.0011 (4)0.0025 (4)
N20.0560 (6)0.0423 (5)0.0210 (4)0.0017 (5)0.0019 (4)0.0023 (4)
C10.0499 (7)0.0359 (6)0.0305 (5)0.0008 (5)0.0019 (5)0.0013 (4)
C20.0999 (13)0.0369 (6)0.0326 (6)0.0043 (7)0.0140 (7)0.0045 (5)
C30.0977 (13)0.0368 (6)0.0303 (6)0.0043 (7)0.0150 (7)0.0051 (5)
C40.0247 (4)0.0241 (4)0.0241 (4)0.0000 (3)0.0013 (3)0.0009 (3)
C50.0256 (4)0.0224 (4)0.0252 (4)0.0035 (3)0.0021 (3)0.0022 (3)
C60.0286 (4)0.0207 (4)0.0215 (4)0.0005 (3)0.0010 (3)0.0016 (3)
Geometric parameters (Å, º) top
O1—C41.4089 (12)N2—C11.3169 (15)
O1—H70.87 (2)N2—C21.3651 (18)
O2—C51.2138 (12)N2—H30.920 (18)
O3—C51.3031 (12)C1—H20.927 (18)
O3—H80.883 (18)C2—C31.3420 (18)
O4—C61.2622 (12)C2—H40.98 (2)
O5—C61.2383 (12)C3—H50.953 (17)
N1—C11.3200 (15)C4—C51.5279 (13)
N1—C31.3659 (18)C4—C61.5384 (13)
N1—H10.901 (15)C4—H60.980 (13)
O1···H12.672 (17)O3···N2v3.1798 (15)
O1···C5i3.1489 (14)O3···C6vi3.2669 (12)
O1···N13.1909 (16)O3···C4iv3.3538 (14)
O1···C6i3.2250 (13)O4···C5vii3.2822 (13)
O1···C33.335 (2)O5···H4viii2.64 (2)
O2···H2ii2.734 (17)O5···H8vii2.742 (15)
O2···C2iii3.2806 (18)O5···C1ix3.2983 (17)
O3···H6iv2.629 (13)O5···C2viii3.3493 (19)
O3···H3v2.66 (2)
C4—O1—H7107.7 (13)N1—C3—H5118.2 (11)
C5—O3—H8109.9 (10)C2—C3—H5134.5 (11)
C1—N1—C3108.38 (10)O1—C4—C5110.15 (8)
C1—N1—H1128.6 (11)O1—C4—C6109.90 (8)
C3—N1—H1123.0 (11)O1—C4—H6112.2 (8)
C1—N2—C2108.80 (10)C5—C4—C6110.03 (8)
C1—N2—H3127.1 (13)C5—C4—H6106.5 (8)
C2—N2—H3124.1 (13)C6—C4—H6108.0 (8)
N1—C1—N2108.71 (11)O2—C5—O3126.13 (9)
N1—C1—H2130.3 (9)O2—C5—C4120.93 (9)
N2—C1—H2121.0 (9)O3—C5—C4112.94 (8)
N2—C2—C3106.82 (12)O4—C6—O5124.77 (9)
N2—C2—H4123.4 (11)O4—C6—C4115.82 (8)
C3—C2—H4129.7 (11)O5—C6—C4119.40 (8)
N1—C3—C2107.28 (12)
O1—C4—C5—O26.25 (12)O5—C6—C4—C599.40 (11)
O1—C4—C5—O3173.06 (8)N1—C1—N2—C20.24 (17)
O1—C4—C6—O4159.04 (9)N1—C3—C2—N20.0 (2)
O1—C4—C6—O522.06 (12)N2—C1—N1—C30.22 (17)
O2—C5—C4—C6115.07 (10)C1—N1—C3—C20.1 (2)
O3—C5—C4—C665.62 (10)C1—N2—C2—C30.2 (2)
O4—C6—C4—C579.49 (11)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y1/2, z+1; (iii) x+1, y, z+1; (iv) x1/2, y+1/2, z; (v) x, y, z1; (vi) x+1/2, y1/2, z; (vii) x+1/2, y+1/2, z; (viii) x+1/2, y+1/2, z+1; (ix) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H7···O20.87 (2)2.18 (2)2.6552 (12)114 (2)
O1—H7···O5i0.87 (2)2.48 (2)3.1150 (16)130 (2)
O3—H8···O4vi0.88 (2)1.67 (2)2.5361 (14)169 (2)
N1—H1···O50.90 (2)1.83 (2)2.7116 (15)167 (2)
N2—H3···O4x0.92 (2)1.88 (2)2.7662 (14)163 (2)
C1—H2···O1ix0.93 (2)2.52 (2)3.3667 (18)153 (1)
C2—H4···O2iii0.98 (2)2.49 (2)3.280 (2)138 (2)
C2—H4···O3x0.98 (2)2.52 (2)3.1347 (18)120 (1)
C3—H5···O20.95 (2)2.46 (2)3.3841 (19)163 (2)
Symmetry codes: (i) x+1/2, y+1/2, z; (iii) x+1, y, z+1; (vi) x+1/2, y1/2, z; (ix) x+1, y+1, z+1; (x) x, y, z+1.
 

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