Ethyl­ene­diaminium pyridine-2,5-dicarboxyl­ate dihydrate

The title compound, C₂H₁₀N₂²⁺·C₇H₃NO₄²⁻·2H₂O, forms a three-dimensional hydrogen-bonded framework structure in which both of the amine groups of ethyl­enediamine are protonated and participate in a total of six hydrogen-bonding inter­actions with carboxyl­ate O-atom acceptors of the anions as well as the water mol­ecules. The cations lie on crystallographic inversion centres and adopt extended conformations, while the anions have twofold rotational symmetry. This results in the pyridine N atom and its ortho-related CH group being disordered over two 50% occupancy sites.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.058
• wR factor = 0.183
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.49
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C2     -   C3     ...       1.38 Ang.

   0 ALERT level A = In general: serious problem
   0 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
   2 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

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 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.

1,2-ethanediaminium pyridine-2,5-dicarboxylate dihydrate

Crystal data

C2H10N2^2+·C7H3NO4^2^−·2H2O	F(000) = 560
Mr = 263.26	Dx = 1.428 Mg m^−3
Monoclinic, C2/c	Melting point: 527 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 11.4733 (16) Å	Cell parameters from 25 reflections
b = 12.1572 (13) Å	θ = 12.6–17.4°
c = 10.0129 (13) Å	µ = 0.12 mm^−1
β = 118.750 (9)°	T = 297 K
V = 1224.5 (3) Å^3	Plate, colourless
Z = 4	0.30 × 0.30 × 0.12 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.016
Radiation source: Rigaku rotating anode	θmax = 27.5°, θmin = 2.6°
Graphite monochromator	h = −6→14
ω–2θ scans	k = −15→7
1699 measured reflections	l = −12→11
1408 independent reflections	3 standard reflections every 150 min
1017 reflections with I > 2σ(I)'	intensity decay: 2.5%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.183	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 9.335P] where P = (Fo^2 + 2Fc^2)/3
1408 reflections	(Δ/σ)max < 0.001
102 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O211	0.8112 (2)	0.17724 (19)	0.3459 (2)	0.0420 (7)
O212	0.7568 (3)	0.0087 (2)	0.3788 (3)	0.0551 (9)
N1	0.9542 (4)	0.0086 (3)	0.6736 (4)	0.060 (8)	0.500
C1	1.0458 (4)	0.0086 (3)	0.8264 (4)	0.062 (10)	0.500
C2	0.9144 (3)	0.1041 (2)	0.5968 (3)	0.0277 (8)
C3	0.9576 (3)	0.2030 (2)	0.6720 (3)	0.0314 (8)
C21	0.8203 (3)	0.0963 (3)	0.4274 (3)	0.0320 (8)
N11	0.3332 (3)	0.1279 (2)	0.4665 (3)	0.0329 (8)
C11	0.3218 (3)	0.2380 (3)	0.5228 (3)	0.0328 (9)
O1W	0.6097 (2)	0.1046 (2)	0.6130 (3)	0.0453 (8)
H1	1.07600	−0.05700	0.87900	0.0650*	0.500
H3	0.92800	0.26900	0.61900	0.0370*
H11	0.35370	0.29230	0.48030	0.0390*
H12	0.37270	0.23980	0.63070	0.0390*
H111	0.284 (4)	0.134 (3)	0.355 (5)	0.050 (10)*
H112	0.295 (4)	0.082 (4)	0.497 (5)	0.058 (13)*
H113	0.421 (5)	0.108 (3)	0.509 (5)	0.062 (13)*
H1W	0.636 (5)	0.176 (4)	0.626 (5)	0.069 (15)*
H2W	0.657 (5)	0.064 (4)	0.699 (6)	0.074 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O211	0.0502 (14)	0.0371 (12)	0.0275 (11)	−0.0023 (10)	0.0098 (10)	0.0030 (9)
O212	0.0721 (18)	0.0549 (16)	0.0316 (12)	−0.0354 (14)	0.0195 (12)	−0.0150 (11)
N1	0.083 (18)	0.028 (11)	0.050 (13)	−0.011 (9)	0.016 (14)	−0.006 (7)
C1	0.092 (19)	0.029 (17)	0.036 (13)	−0.004 (13)	0.008 (12)	0.001 (9)
C2	0.0311 (14)	0.0259 (14)	0.0243 (13)	−0.0013 (11)	0.0120 (11)	−0.0007 (10)
C3	0.0393 (16)	0.0214 (13)	0.0279 (14)	0.0003 (11)	0.0117 (12)	0.0020 (11)
C21	0.0330 (14)	0.0346 (15)	0.0264 (14)	−0.0057 (12)	0.0127 (12)	−0.0045 (11)
N11	0.0342 (14)	0.0315 (14)	0.0296 (13)	0.0047 (11)	0.0127 (11)	−0.0001 (10)
C11	0.0329 (16)	0.0328 (16)	0.0291 (14)	0.0011 (12)	0.0121 (12)	−0.0017 (12)
O1W	0.0398 (13)	0.0393 (14)	0.0384 (13)	0.0019 (11)	0.0040 (10)	0.0060 (11)

Geometric parameters (Å, º)

O211—C21	1.250 (4)	C1—C2^i	1.345 (4)
O212—C21	1.249 (4)	C2—C3	1.378 (4)
O1W—H1W	0.91 (5)	C2—C21	1.513 (4)
O1W—H2W	0.91 (5)	C3—C3^i	1.387 (4)
N1—C2	1.345 (4)	C1—H1	0.9300
N1—C1	1.378 (5)	C3—H3	0.9300
N11—C11	1.482 (4)	C11—C11^ii	1.511 (5)
N11—H112	0.85 (5)	C11—H12	0.9500
N11—H111	0.98 (4)	C11—H11	0.9500
N11—H113	0.92 (6)
H1W—O1W—H2W	112 (4)	O211—C21—O212	124.5 (3)
C1—N1—C2	120.2 (3)	O212—C21—C2	117.3 (3)
C11—N11—H113	110 (2)	O211—C21—C2	118.2 (3)
H111—N11—H112	110 (4)	N1—C1—H1	121.00
H112—N11—H113	108 (4)	C2^i—C1—H1	119.00
C11—N11—H112	108 (3)	C3^i—C3—H3	121.00
C11—N11—H111	105 (2)	C2—C3—H3	120.00
H111—N11—H113	117 (4)	N11—C11—C11^ii	110.0 (3)
N1—C1—C2^i	120.2 (3)	N11—C11—H11	110.00
C3—C2—C21	122.8 (2)	N11—C11—H12	110.00
N1—C2—C21	116.7 (3)	C11^ii—C11—H11	109.00
N1—C2—C3	120.4 (3)	C11^ii—C11—H12	109.00
C2—C3—C3^i	119.2 (2)	H11—C11—H12	110.00
C2—N1—C1—C2^i	6.9 (7)	N1—C2—C21—O212	20.3 (5)
C1—N1—C2—C3	−4.5 (7)	C3—C2—C21—O212	−159.0 (4)
C1—N1—C2—C21	176.2 (4)	C3—C2—C21—O211	21.0 (5)
N1—C1—C2^i—C3^i	−4.5 (7)	C21—C2—C3—C3^i	179.1 (3)
N1—C1—C2^i—C21^i	176.2 (4)	C2—C3—C3^i—C2^i	2.5 (6)
N1—C2—C3—C3^i	−0.2 (6)	N11—C11—C11^ii—N11^ii	−180.0 (2)
N1—C2—C21—O211	−159.8 (4)

Symmetry codes: (i) −x+2, y, −z+3/2; (ii) −x+1/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O211^iii	0.91 (5)	1.86 (5)	2.769 (3)	179 (7)
O1W—H2W···O212^iv	0.91 (5)	1.83 (5)	2.740 (4)	176 (5)
N11—H111···O211^v	0.98 (4)	1.85 (4)	2.811 (3)	168 (4)
N11—H112···O212^vi	0.85 (5)	1.96 (5)	2.786 (4)	164 (4)
N11—H113···O1W	0.92 (6)	1.90 (6)	2.796 (4)	166 (3)

Symmetry codes: (iii) −x+3/2, −y+1/2, −z+1; (iv) x, −y, z+1/2; (v) −x+1, y, −z+1/2; (vi) −x+1, −y, −z+1.