Imidazolium hydrogen tartronate

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.

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

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)

Crystal data

C3H5N2^+·C3H3O5^−	F(000) = 392.00
Mr = 188.14	Dx = 1.525 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 25 reflections
a = 8.5516 (15) Å	θ = 11.1–11.5°
b = 10.2077 (17) Å	µ = 0.13 mm^−1
c = 9.392 (3) Å	T = 298 K
β = 91.64 (2)°	Prismatic, colorless
V = 819.6 (3) Å^3	0.50 × 0.40 × 0.35 mm
Z = 4

Data collection

Rigaku AFC-5R diffractometer	2032 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.021
Graphite monochromator	θmax = 31.0°, θmin = 2.2°
ω–2θ scans	h = −2→12
Absorption correction: ψ scan (North et al., 1968)	k = −14→14
Tmin = 0.88, Tmax = 0.95	l = −13→13
6785 measured reflections	3 standard reflections every 97 reflections
2617 independent reflections	intensity decay: 4.2%

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.065	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo) + 0.00181|Fo|^2]
wR(F^2) = 0.120	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 0.36 e Å^−3
2617 reflections	Δρmin = −0.27 e Å^−3
151 parameters	Extinction correction: Zachariasen (1967), equ(3) Acta Cryst.(1968) 24, p. 213.
0 restraints	Extinction coefficient: 1.43E-5 (12)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.59735 (10)	0.28719 (8)	0.24917 (9)	0.0351 (2)
O2	0.43495 (10)	0.06705 (8)	0.21603 (8)	0.0364 (2)
O3	0.34469 (10)	0.12441 (7)	−0.00186 (7)	0.03182 (19)
O4	0.31606 (10)	0.41559 (8)	0.00493 (7)	0.0355 (2)
O5	0.34176 (11)	0.43865 (8)	0.23900 (8)	0.0378 (2)
N1	0.37412 (14)	0.34483 (11)	0.50833 (10)	0.0396 (3)
N2	0.35097 (14)	0.31784 (11)	0.73300 (10)	0.0397 (3)
C1	0.34872 (16)	0.40520 (12)	0.62979 (12)	0.0388 (3)
C2	0.3781 (3)	0.19715 (14)	0.67617 (14)	0.0563 (4)
C3	0.3926 (2)	0.21421 (13)	0.53549 (14)	0.0547 (4)
C4	0.50116 (11)	0.27806 (9)	0.12526 (10)	0.0243 (2)
C5	0.42193 (11)	0.14398 (9)	0.11786 (10)	0.0244 (2)
C6	0.37693 (11)	0.38707 (9)	0.12497 (9)	0.0236 (2)
H1	0.378 (2)	0.3793 (17)	0.4202 (16)	0.059 (5)*
H2	0.329 (2)	0.4929 (18)	0.6482 (14)	0.054 (5)*
H3	0.335 (2)	0.333 (2)	0.8282 (19)	0.072 (5)*
H4	0.380 (3)	0.116 (2)	0.7324 (19)	0.081 (6)*
H5	0.414 (2)	0.1576 (18)	0.4577 (17)	0.063 (5)*
H6	0.5608 (16)	0.2867 (13)	0.0383 (14)	0.029 (3)*
H7	0.616 (2)	0.208 (2)	0.2794 (19)	0.074 (6)*
H8	0.300 (2)	0.0466 (17)	−0.0009 (15)	0.052 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0334 (4)	0.0333 (4)	0.0377 (4)	0.0012 (3)	−0.0137 (3)	−0.0020 (3)
O2	0.0468 (5)	0.0279 (4)	0.0341 (4)	0.0025 (3)	−0.0050 (3)	0.0071 (3)
O3	0.0440 (5)	0.0261 (4)	0.0251 (3)	−0.0073 (3)	−0.0032 (3)	−0.0019 (3)
O4	0.0534 (5)	0.0317 (4)	0.0210 (3)	0.0143 (3)	−0.0066 (3)	−0.0006 (3)
O5	0.0505 (5)	0.0414 (4)	0.0217 (3)	0.0169 (4)	0.0002 (3)	−0.0024 (3)
N1	0.0550 (6)	0.0413 (5)	0.0224 (4)	−0.0055 (5)	−0.0011 (4)	0.0025 (4)
N2	0.0560 (6)	0.0423 (5)	0.0210 (4)	0.0017 (5)	0.0019 (4)	−0.0023 (4)
C1	0.0499 (7)	0.0359 (6)	0.0305 (5)	0.0008 (5)	−0.0019 (5)	−0.0013 (4)
C2	0.0999 (13)	0.0369 (6)	0.0326 (6)	0.0043 (7)	0.0140 (7)	0.0045 (5)
C3	0.0977 (13)	0.0368 (6)	0.0303 (6)	−0.0043 (7)	0.0150 (7)	−0.0051 (5)
C4	0.0247 (4)	0.0241 (4)	0.0241 (4)	0.0000 (3)	−0.0013 (3)	−0.0009 (3)
C5	0.0256 (4)	0.0224 (4)	0.0252 (4)	0.0035 (3)	0.0021 (3)	−0.0022 (3)
C6	0.0286 (4)	0.0207 (4)	0.0215 (4)	−0.0005 (3)	−0.0010 (3)	0.0016 (3)

Geometric parameters (Å, º)

O1—C4	1.4089 (12)	N2—C1	1.3169 (15)
O1—H7	0.87 (2)	N2—C2	1.3651 (18)
O2—C5	1.2138 (12)	N2—H3	0.920 (18)
O3—C5	1.3031 (12)	C1—H2	0.927 (18)
O3—H8	0.883 (18)	C2—C3	1.3420 (18)
O4—C6	1.2622 (12)	C2—H4	0.98 (2)
O5—C6	1.2383 (12)	C3—H5	0.953 (17)
N1—C1	1.3200 (15)	C4—C5	1.5279 (13)
N1—C3	1.3659 (18)	C4—C6	1.5384 (13)
N1—H1	0.901 (15)	C4—H6	0.980 (13)
O1···H1	2.672 (17)	O3···N2^v	3.1798 (15)
O1···C5^i	3.1489 (14)	O3···C6^vi	3.2669 (12)
O1···N1	3.1909 (16)	O3···C4^iv	3.3538 (14)
O1···C6^i	3.2250 (13)	O4···C5^vii	3.2822 (13)
O1···C3	3.335 (2)	O5···H4^viii	2.64 (2)
O2···H2^ii	2.734 (17)	O5···H8^vii	2.742 (15)
O2···C2^iii	3.2806 (18)	O5···C1^ix	3.2983 (17)
O3···H6^iv	2.629 (13)	O5···C2^viii	3.3493 (19)
O3···H3^v	2.66 (2)
C4—O1—H7	107.7 (13)	N1—C3—H5	118.2 (11)
C5—O3—H8	109.9 (10)	C2—C3—H5	134.5 (11)
C1—N1—C3	108.38 (10)	O1—C4—C5	110.15 (8)
C1—N1—H1	128.6 (11)	O1—C4—C6	109.90 (8)
C3—N1—H1	123.0 (11)	O1—C4—H6	112.2 (8)
C1—N2—C2	108.80 (10)	C5—C4—C6	110.03 (8)
C1—N2—H3	127.1 (13)	C5—C4—H6	106.5 (8)
C2—N2—H3	124.1 (13)	C6—C4—H6	108.0 (8)
N1—C1—N2	108.71 (11)	O2—C5—O3	126.13 (9)
N1—C1—H2	130.3 (9)	O2—C5—C4	120.93 (9)
N2—C1—H2	121.0 (9)	O3—C5—C4	112.94 (8)
N2—C2—C3	106.82 (12)	O4—C6—O5	124.77 (9)
N2—C2—H4	123.4 (11)	O4—C6—C4	115.82 (8)
C3—C2—H4	129.7 (11)	O5—C6—C4	119.40 (8)
N1—C3—C2	107.28 (12)
O1—C4—C5—O2	6.25 (12)	O5—C6—C4—C5	99.40 (11)
O1—C4—C5—O3	−173.06 (8)	N1—C1—N2—C2	−0.24 (17)
O1—C4—C6—O4	159.04 (9)	N1—C3—C2—N2	−0.0 (2)
O1—C4—C6—O5	−22.06 (12)	N2—C1—N1—C3	0.22 (17)
O2—C5—C4—C6	−115.07 (10)	C1—N1—C3—C2	−0.1 (2)
O3—C5—C4—C6	65.62 (10)	C1—N2—C2—C3	0.2 (2)
O4—C6—C4—C5	−79.49 (11)

Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) −x+1/2, y−1/2, −z+1; (iii) −x+1, −y, −z+1; (iv) x−1/2, −y+1/2, z; (v) x, y, z−1; (vi) −x+1/2, y−1/2, −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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H7···O2	0.87 (2)	2.18 (2)	2.6552 (12)	114 (2)
O1—H7···O5^i	0.87 (2)	2.48 (2)	3.1150 (16)	130 (2)
O3—H8···O4^vi	0.88 (2)	1.67 (2)	2.5361 (14)	169 (2)
N1—H1···O5	0.90 (2)	1.83 (2)	2.7116 (15)	167 (2)
N2—H3···O4^x	0.92 (2)	1.88 (2)	2.7662 (14)	163 (2)
C1—H2···O1^ix	0.93 (2)	2.52 (2)	3.3667 (18)	153 (1)
C2—H4···O2^iii	0.98 (2)	2.49 (2)	3.280 (2)	138 (2)
C2—H4···O3^x	0.98 (2)	2.52 (2)	3.1347 (18)	120 (1)
C3—H5···O2	0.95 (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, y−1/2, −z; (ix) −x+1, −y+1, −z+1; (x) x, y, z+1.