Crystal structure of 2-amino-4-methyl­pyridin-1-ium (2R,3R)-3-carb­oxy-2,3-di­hydroxy­propano­ate monohydrate

Jovita, J.V.; Sathya, S.; Usha, G.; Vasanthi, R.; Ramanand, A.

doi:10.1107/S160053681401842X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1036-o1037

doi:10.1107/S160053681401842X

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Crystal structure of 2-amino-4-methylpyridin-1-ium (2R,3R)-3-carboxy-2,3-dihydroxypropanoate monohydrate

J. V. Jovita,^a S. Sathya,^a G. Usha,^a ^* R. Vasanthi ^a and A. Ramanand ^b

^aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and ^bDepartment of Physics, Loyola College, Chennai-34, Tamilnadu, India
^*Correspondence e-mail: guqmc@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 28 June 2014; accepted 13 August 2014; online 23 August 2014)

The title molecular salt, C₆H₉N₂⁺·C₄H₅O₆⁻·H₂O, crystallized with two 2-amino-4-methylpyridin-1-ium cations, two L-(+)-tartaric acid monoanions [systematic name: (2R,3R)-3-carboxy-2,3-dihydroxypropanoate] and two water molecules in the asymmetric unit. In the crystal, the cations, anions and water molecules are linked via a number of O—H⋯O and N—H⋯O hydrogen bonds, and a C—H⋯O hydrogen bond, forming a three-dimensional structure

Keywords: crystal structure; 2-amino-4-methylpyridin-1-ium; tartrate; L-(+)-tartaric acid.

CCDC reference: 1019274

1. Related literature

For the biological activity of pyridinium derivatives, see: Judge & Bever (2006 ); Schwid et al. (1997 ); Strupp et al. (2004 ). For the crystal structure of a related molecular salt involving the 2-amino-4-methylpyridin-1-ium cation, see: Hemamalini & Fun (2010 ).

2. Experimental

2.1. Crystal data

C₆H₉N₂⁺·C₄H₅O₆⁻·H₂O
M_r = 276.25
Triclinic, P 1
a = 7.176 (3) Å
b = 9.9359 (18) Å
c = 10.716 (2) Å
α = 117.528 (5)°
β = 104.792 (7)°
γ = 91.701 (7)°
V = 645.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.20 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.971, T_max = 0.976
10211 measured reflections
4999 independent reflections
4769 reflections with I > 2σ(I)
R_int = 0.022

2.3. Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.088
S = 1.08
4999 reflections
410 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2	0.87 (3)	1.86 (3)	2.725 (3)	172 (3)
O1W—H1WB⋯O3ⁱ	0.78 (3)	2.39 (4)	3.012 (3)	137 (3)
O1W—H1WB⋯O12	0.78 (3)	2.39 (3)	3.006 (3)	137 (3)
O3—H3⋯O2	0.82 (4)	1.95 (4)	2.562 (2)	131 (4)
O3—H3⋯O7	0.82 (4)	2.51 (4)	3.072 (3)	127 (3)
N2—H2NA⋯O1Wⁱⁱ	0.84 (3)	2.00 (3)	2.819 (3)	164 (3)
N3—H3N⋯O4	0.84 (3)	2.15 (3)	2.939 (3)	157 (3)
N3—H3N⋯O6	0.84 (3)	2.44 (3)	3.047 (3)	130 (3)
N2—H2NB⋯O8ⁱⁱⁱ	0.83 (4)	2.41 (3)	3.032 (3)	132 (3)
N2—H2NB⋯O9ⁱⁱⁱ	0.83 (4)	2.21 (4)	2.942 (3)	147 (3)
O4—H4A⋯O11^iv	0.90 (4)	1.88 (4)	2.732 (3)	156 (3)
O2W—H2WA⋯O8ⁱ	0.82 (4)	2.00 (4)	2.819 (3)	173 (4)
O5—H5A⋯O1ⁱⁱ	1.16 (4)	1.41 (4)	2.534 (2)	163 (4)
N4—H4NA⋯O3	0.88 (3)	2.12 (3)	2.968 (3)	163 (3)
O7—H7A⋯O12ⁱⁱ	1.09 (4)	1.39 (4)	2.476 (2)	174 (4)
N4—H4NB⋯O2Wⁱⁱ	0.83 (4)	2.32 (4)	3.128 (4)	164 (3)
N4—H4NB⋯O12ⁱⁱ	0.83 (4)	2.60 (4)	2.955 (4)	108 (3)
O9—H9⋯O2W	0.91 (3)	1.81 (3)	2.715 (3)	172 (3)
O10—H10A⋯O6^v	0.83 (3)	2.19 (3)	2.912 (3)	145 (3)
O10—H10A⋯O11	0.83 (3)	2.15 (3)	2.648 (3)	119 (3)
N1—H29⋯O10ⁱⁱⁱ	0.78 (3)	2.24 (3)	2.946 (3)	151 (3)
C5—H5⋯O6^vi	0.93	2.46	3.158 (3)	132
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) x-1, y-1, z-1; (iv) x-1, y-1, z; (v) x+1, y+1, z; (vi) x, y, z-1.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1019274

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053681401842X/su2748sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681401842X/su2748Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681401842X/su2748Isup3.cml

checkCIF report

Related literature top

For the biological activity of pyridinium derivatives, see: Judge & Bever (2006); Schwid et al. (1997); Strupp et al. (2004). For the crystal structure of a related molecular salt involving the 2-amino-4-methylpyridin-1-ium cation, see: Hemamalini & Fun (2010).

Experimental top

The title compound was prepared by mixing an equimolar ratio of 4-methylpyridin-2-amine (Aldrich) with L-(+)-tartaric acid (Spectrochem). When the tartaric acid was added to a saturated solution of 4-methylpyridin-2-amine in acetone a pale pink coloured precipitate was formed. The precipitate was collected and allowed to dry and powdered. Suitable crystals of the title salt were prepared by slow evaporation of a solution of the powder in methanol at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

2-Amino-4-methylpyridin-1-ium (2R,3R)-3-carboxy-2,3-dihydroxypropanoate monohydrate top

Crystal data top

C₆H₉N₂⁺·C₄H₅O₆⁻·H₂O	Z = 2
M_r = 276.25	F(000) = 292
Triclinic, P1	D_x = 1.422 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.176 (3) Å	Cell parameters from 8251 reflections
b = 9.9359 (18) Å	θ = 2.3–32.6°
c = 10.716 (2) Å	µ = 0.12 mm⁻¹
α = 117.528 (5)°	T = 293 K
β = 104.792 (7)°	Block, colourless
γ = 91.701 (7)°	0.24 × 0.22 × 0.20 mm
V = 645.3 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	4999 independent reflections
Radiation source: fine-focus sealed tube	4769 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
T_min = 0.971, T_max = 0.976	k = −12→12
10211 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0479P)² + 0.1123P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
4999 reflections	Δρ_max = 0.27 e Å⁻³
410 parameters	Δρ_min = −0.17 e Å⁻³
3 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.055 (5)

Crystal data top

C₆H₉N₂⁺·C₄H₅O₆⁻·H₂O	γ = 91.701 (7)°
M_r = 276.25	V = 645.3 (3) Å³
Triclinic, P1	Z = 2
a = 7.176 (3) Å	Mo Kα radiation
b = 9.9359 (18) Å	µ = 0.12 mm⁻¹
c = 10.716 (2) Å	T = 293 K
α = 117.528 (5)°	0.24 × 0.22 × 0.20 mm
β = 104.792 (7)°

Data collection top

Bruker APEXII CCD diffractometer	4999 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4769 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.976	R_int = 0.022
10211 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	3 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.27 e Å⁻³
4999 reflections	Δρ_min = −0.17 e Å⁻³
410 parameters

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 esds 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	U_iso*/U_eq
O1	0.74569 (19)	0.24776 (17)	0.32479 (15)	0.0425 (4)
O2	0.8383 (2)	0.48800 (17)	0.51261 (16)	0.0434 (4)
O3	0.4999 (2)	0.52134 (16)	0.54862 (17)	0.0421 (5)
O4	0.5543 (2)	0.25906 (18)	0.58628 (16)	0.0402 (4)
O5	0.09901 (19)	0.22642 (16)	0.33245 (15)	0.0385 (4)
O6	0.1808 (2)	0.2985 (2)	0.57363 (17)	0.0469 (5)
O7	0.73206 (18)	0.84899 (15)	0.69807 (16)	0.0366 (4)
O8	0.8096 (2)	1.08215 (17)	0.89449 (17)	0.0443 (4)
O9	1.1844 (2)	1.09612 (17)	0.92901 (15)	0.0408 (4)
O10	1.0198 (2)	1.08903 (18)	0.65507 (18)	0.0440 (5)
O11	1.3678 (3)	1.0395 (2)	0.6194 (3)	0.0676 (8)
O12	1.38559 (17)	0.86225 (14)	0.69019 (15)	0.0340 (4)
C13	0.7165 (2)	0.3699 (2)	0.42355 (19)	0.0302 (5)
C14	0.5072 (3)	0.3760 (2)	0.4327 (2)	0.0299 (5)
C15	0.4308 (2)	0.2468 (2)	0.4546 (2)	0.0295 (5)
C16	0.2212 (2)	0.25924 (19)	0.4604 (2)	0.0298 (5)
C17	0.8533 (2)	0.9703 (2)	0.80181 (19)	0.0286 (5)
C18	1.0658 (2)	0.9648 (2)	0.80165 (19)	0.0275 (5)
C19	1.0873 (2)	0.95937 (19)	0.66195 (19)	0.0290 (5)
C20	1.2990 (2)	0.9559 (2)	0.65682 (19)	0.0300 (5)
N1	0.0123 (3)	0.3863 (2)	−0.09469 (18)	0.0368 (5)
N2	0.0764 (3)	0.3843 (2)	0.1268 (2)	0.0444 (6)
C1	0.0410 (3)	0.4600 (2)	0.0521 (2)	0.0316 (5)
C2	0.0344 (3)	0.6200 (2)	0.1196 (2)	0.0355 (5)
C3	0.0001 (3)	0.6933 (2)	0.0375 (2)	0.0391 (6)
C4	−0.0325 (3)	0.6082 (3)	−0.1162 (2)	0.0417 (7)
C5	−0.0249 (3)	0.4564 (2)	−0.1787 (2)	0.0397 (6)
C6	−0.0012 (5)	0.8623 (3)	0.1096 (3)	0.0639 (9)
N3	0.4969 (3)	0.4655 (2)	0.8719 (2)	0.0450 (6)
N4	0.4515 (3)	0.6816 (3)	0.8476 (3)	0.0535 (8)
O1W	1.1106 (3)	0.58916 (19)	0.42444 (17)	0.0448 (5)
C7	0.5351 (4)	0.3913 (3)	0.9520 (3)	0.0528 (8)
C8	0.5627 (4)	0.4668 (3)	1.0974 (3)	0.0529 (8)
C9	0.5523 (3)	0.6239 (3)	1.1678 (2)	0.0499 (8)
C10	0.5161 (3)	0.6983 (3)	1.0861 (2)	0.0426 (6)
C11	0.4877 (3)	0.6164 (2)	0.9329 (2)	0.0367 (6)
C12	0.5813 (6)	0.7111 (5)	1.3315 (3)	0.0825 (13)
O2W	1.5440 (2)	1.04131 (19)	1.03282 (18)	0.0444 (5)
H3	0.613 (5)	0.565 (4)	0.575 (4)	0.067 (9)*
H4A	0.513 (5)	0.170 (4)	0.582 (3)	0.062 (8)*
H5A	−0.057 (6)	0.230 (4)	0.344 (4)	0.098 (12)*
H14	0.42260	0.36470	0.33960	0.0360*
H15	0.43150	0.14750	0.37120	0.0350*
H7A	0.582 (5)	0.862 (4)	0.698 (4)	0.082 (10)*
H9	1.300 (4)	1.068 (3)	0.959 (3)	0.055 (7)*
H10A	1.091 (4)	1.116 (3)	0.618 (3)	0.053 (7)*
H18	1.10350	0.87210	0.80480	0.0330*
H19	1.00390	0.86590	0.57650	0.0350*
H2	0.05370	0.67540	0.22070	0.0430*
H2NA	0.085 (3)	0.429 (3)	0.217 (3)	0.029 (5)*
H4	−0.05890	0.65630	−0.17380	0.0500*
H2NB	0.071 (5)	0.290 (4)	0.081 (3)	0.058 (8)*
H5	−0.04540	0.39950	−0.27990	0.0480*
H6A	0.09330	0.91180	0.08800	0.0960*
H6B	0.03140	0.90320	0.21460	0.0960*
H6C	−0.12900	0.88070	0.07290	0.0960*
H29	0.015 (4)	0.299 (3)	−0.138 (3)	0.047 (7)*
H3N	0.481 (4)	0.412 (3)	0.781 (3)	0.048 (7)*
H7	0.54230	0.28690	0.90550	0.0630*
H4NA	0.441 (4)	0.624 (3)	0.754 (3)	0.045 (7)*
H8	0.58890	0.41520	1.15170	0.0630*
H4NB	0.452 (5)	0.776 (4)	0.890 (4)	0.068 (10)*
H10	0.51030	0.80290	1.13180	0.0510*
H12A	0.70470	0.69940	1.38340	0.1240*
H12B	0.47770	0.67110	1.35330	0.1240*
H12C	0.57980	0.81830	1.36210	0.1240*
H1WA	1.033 (4)	0.554 (3)	0.457 (3)	0.052 (7)*
H1WB	1.211 (5)	0.620 (3)	0.487 (3)	0.055 (8)*
H2WA	1.617 (5)	1.059 (4)	0.992 (3)	0.062 (9)*
H2WB	1.591 (4)	1.099 (3)	1.125 (4)	0.051 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0253 (6)	0.0529 (9)	0.0359 (7)	0.0069 (6)	0.0113 (5)	0.0098 (7)
O2	0.0303 (7)	0.0451 (8)	0.0468 (8)	−0.0004 (6)	0.0125 (6)	0.0160 (7)
O3	0.0397 (8)	0.0312 (7)	0.0588 (9)	0.0085 (6)	0.0267 (7)	0.0185 (7)
O4	0.0343 (7)	0.0467 (8)	0.0487 (8)	0.0063 (6)	0.0085 (6)	0.0326 (7)
O5	0.0257 (6)	0.0419 (7)	0.0344 (7)	0.0021 (5)	0.0100 (5)	0.0076 (6)
O6	0.0457 (8)	0.0691 (10)	0.0530 (9)	0.0287 (8)	0.0309 (7)	0.0421 (8)
O7	0.0240 (6)	0.0291 (6)	0.0471 (8)	0.0044 (5)	0.0135 (5)	0.0095 (6)
O8	0.0300 (7)	0.0367 (7)	0.0509 (8)	0.0049 (6)	0.0193 (6)	0.0056 (6)
O9	0.0262 (6)	0.0410 (7)	0.0380 (7)	0.0055 (6)	0.0055 (5)	0.0076 (6)
O10	0.0455 (8)	0.0532 (9)	0.0648 (9)	0.0284 (7)	0.0330 (8)	0.0444 (8)
O11	0.0513 (9)	0.0784 (12)	0.1307 (18)	0.0294 (9)	0.0552 (11)	0.0819 (13)
O12	0.0245 (6)	0.0340 (7)	0.0484 (7)	0.0084 (5)	0.0153 (5)	0.0215 (6)
C13	0.0263 (8)	0.0413 (10)	0.0292 (8)	0.0072 (8)	0.0106 (7)	0.0209 (8)
C14	0.0258 (8)	0.0355 (9)	0.0334 (9)	0.0074 (7)	0.0111 (7)	0.0196 (7)
C15	0.0262 (8)	0.0291 (8)	0.0336 (9)	0.0057 (7)	0.0115 (7)	0.0142 (7)
C16	0.0286 (9)	0.0254 (8)	0.0402 (9)	0.0063 (7)	0.0156 (7)	0.0170 (7)
C17	0.0255 (8)	0.0306 (9)	0.0342 (9)	0.0070 (7)	0.0123 (7)	0.0176 (7)
C18	0.0233 (8)	0.0249 (8)	0.0357 (9)	0.0063 (6)	0.0106 (7)	0.0150 (7)
C19	0.0242 (8)	0.0291 (9)	0.0362 (9)	0.0073 (7)	0.0117 (7)	0.0164 (8)
C20	0.0286 (8)	0.0274 (8)	0.0360 (9)	0.0053 (7)	0.0153 (7)	0.0141 (7)
N1	0.0436 (9)	0.0281 (8)	0.0353 (8)	0.0098 (7)	0.0149 (7)	0.0109 (7)
N2	0.0646 (12)	0.0312 (9)	0.0364 (10)	0.0133 (8)	0.0164 (8)	0.0149 (8)
C1	0.0290 (8)	0.0311 (9)	0.0334 (9)	0.0063 (7)	0.0106 (7)	0.0140 (8)
C2	0.0381 (10)	0.0292 (9)	0.0329 (9)	0.0061 (7)	0.0124 (8)	0.0093 (8)
C3	0.0349 (10)	0.0307 (10)	0.0507 (11)	0.0032 (8)	0.0128 (9)	0.0193 (9)
C4	0.0407 (11)	0.0459 (12)	0.0473 (11)	0.0082 (9)	0.0135 (9)	0.0295 (10)
C5	0.0385 (10)	0.0480 (12)	0.0335 (9)	0.0073 (8)	0.0123 (8)	0.0198 (9)
C6	0.0813 (19)	0.0347 (12)	0.0725 (17)	0.0119 (12)	0.0208 (15)	0.0248 (12)
N3	0.0541 (11)	0.0444 (10)	0.0342 (9)	0.0062 (8)	0.0122 (8)	0.0179 (8)
N4	0.0698 (14)	0.0596 (13)	0.0480 (12)	0.0180 (11)	0.0234 (10)	0.0365 (11)
O1W	0.0442 (8)	0.0447 (8)	0.0366 (8)	−0.0045 (7)	0.0102 (7)	0.0143 (7)
C7	0.0550 (13)	0.0454 (12)	0.0626 (15)	0.0048 (10)	0.0142 (11)	0.0320 (12)
C8	0.0500 (13)	0.0651 (15)	0.0577 (14)	0.0048 (11)	0.0122 (11)	0.0435 (13)
C9	0.0369 (11)	0.0773 (17)	0.0395 (11)	0.0048 (11)	0.0085 (9)	0.0334 (12)
C10	0.0403 (11)	0.0472 (12)	0.0404 (10)	0.0109 (9)	0.0156 (9)	0.0194 (9)
C11	0.0319 (9)	0.0461 (11)	0.0376 (10)	0.0063 (8)	0.0126 (7)	0.0238 (9)
C12	0.092 (2)	0.108 (3)	0.0447 (14)	0.019 (2)	0.0205 (15)	0.0349 (16)
O2W	0.0345 (7)	0.0524 (9)	0.0328 (8)	0.0026 (6)	0.0055 (6)	0.0125 (7)

Geometric parameters (Å, º) top

O1—C13	1.256 (2)	C2—C3	1.363 (3)
O2—C13	1.237 (3)	N2—H2NA	0.84 (3)
O3—C14	1.418 (3)	N2—H2NB	0.83 (4)
O4—C15	1.410 (2)	C3—C4	1.410 (3)
O5—C16	1.308 (2)	C3—C6	1.491 (4)
O6—C16	1.207 (2)	C4—C5	1.348 (4)
O3—H3	0.82 (4)	C2—H2	0.9300
O4—H4A	0.90 (4)	N3—C11	1.342 (3)
O5—H5A	1.16 (4)	N3—C7	1.354 (4)
O7—C17	1.285 (2)	N4—C11	1.326 (4)
O8—C17	1.216 (3)	C4—H4	0.9300
O9—C18	1.409 (2)	C5—H5	0.9300
O10—C19	1.417 (3)	C6—H6A	0.9600
O11—C20	1.216 (3)	C6—H6B	0.9600
O12—C20	1.268 (3)	C6—H6C	0.9600
C13—C14	1.531 (3)	N3—H3N	0.84 (3)
C14—C15	1.519 (3)	N4—H4NB	0.83 (4)
C15—C16	1.527 (2)	N4—H4NA	0.88 (3)
O7—H7A	1.09 (4)	C7—C8	1.335 (4)
O9—H9	0.91 (3)	C8—C9	1.399 (4)
O10—H10A	0.83 (3)	C9—C10	1.369 (4)
C14—H14	0.9800	C9—C12	1.506 (3)
C15—H15	0.9800	C10—C11	1.408 (3)
C17—C18	1.528 (2)	O1W—H1WB	0.78 (3)
C18—C19	1.520 (3)	O1W—H1WA	0.87 (3)
C19—C20	1.535 (2)	C7—H7	0.9300
N1—C5	1.355 (3)	C8—H8	0.9300
N1—C1	1.347 (3)	C10—H10	0.9300
N2—C1	1.317 (3)	C12—H12C	0.9600
C18—H18	0.9800	C12—H12A	0.9600
C19—H19	0.9800	C12—H12B	0.9600
C1—C2	1.418 (3)	O2W—H2WA	0.82 (4)
N1—H29	0.78 (3)	O2W—H2WB	0.84 (4)

C14—O3—H3	100 (3)	C1—N2—H2NB	119 (2)
C15—O4—H4A	103.0 (19)	C1—C2—C3	120.58 (17)
C16—O5—H5A	108.0 (18)	H2NA—N2—H2NB	121 (3)
O1—C13—C14	116.99 (16)	C2—C3—C4	119.4 (2)
O1—C13—O2	126.88 (16)	C4—C3—C6	120.2 (2)
O2—C13—C14	116.10 (17)	C2—C3—C6	120.37 (19)
O3—C14—C13	109.65 (16)	C3—C4—C5	119.3 (2)
O3—C14—C15	110.52 (16)	N1—C5—C4	120.27 (18)
C13—C14—C15	111.91 (17)	C1—C2—H2	120.00
C14—C15—C16	108.80 (17)	C3—C2—H2	120.00
O4—C15—C14	108.89 (16)	C7—N3—C11	122.6 (2)
O4—C15—C16	111.36 (15)	C5—C4—H4	120.00
O5—C16—O6	126.04 (16)	C3—C4—H4	120.00
O5—C16—C15	112.27 (15)	N1—C5—H5	120.00
O6—C16—C15	121.67 (16)	C4—C5—H5	120.00
C17—O7—H7A	111 (2)	C3—C6—H6B	109.00
C18—O9—H9	107.2 (19)	C3—C6—H6C	109.00
C19—O10—H10A	106 (2)	C3—C6—H6A	109.00
O3—C14—H14	108.00	H6A—C6—H6C	110.00
C13—C14—H14	108.00	H6B—C6—H6C	109.00
C15—C14—H14	108.00	H6A—C6—H6B	109.00
C16—C15—H15	109.00	C11—N3—H3N	121 (2)
O4—C15—H15	109.00	C7—N3—H3N	116 (2)
C14—C15—H15	109.00	C11—N4—H4NA	118 (2)
O7—C17—C18	114.13 (16)	H4NA—N4—H4NB	126 (3)
O7—C17—O8	125.05 (16)	C11—N4—H4NB	116 (3)
O8—C17—C18	120.83 (17)	N3—C7—C8	120.5 (3)
O9—C18—C17	108.17 (14)	C7—C8—C9	119.9 (3)
O9—C18—C19	111.32 (16)	C8—C9—C12	120.8 (3)
C17—C18—C19	109.84 (14)	C10—C9—C12	120.1 (3)
C18—C19—C20	112.12 (14)	C8—C9—C10	119.2 (2)
O10—C19—C18	108.04 (15)	C9—C10—C11	120.0 (2)
O10—C19—C20	111.07 (16)	N3—C11—C10	117.8 (2)
O11—C20—O12	125.81 (18)	N4—C11—C10	122.9 (2)
O11—C20—C19	118.3 (2)	N3—C11—N4	119.2 (2)
O12—C20—C19	115.93 (17)	H1WA—O1W—H1WB	105 (3)
C1—N1—C5	123.5 (2)	N3—C7—H7	120.00
C17—C18—H18	109.00	C8—C7—H7	120.00
C19—C18—H18	109.00	C9—C8—H8	120.00
O9—C18—H18	109.00	C7—C8—H8	120.00
C18—C19—H19	109.00	C9—C10—H10	120.00
C20—C19—H19	108.00	C11—C10—H10	120.00
O10—C19—H19	109.00	C9—C12—H12B	109.00
N1—C1—N2	120.2 (2)	C9—C12—H12C	109.00
N1—C1—C2	116.89 (19)	C9—C12—H12A	109.00
N2—C1—C2	122.93 (18)	H12A—C12—H12C	110.00
C5—N1—H29	115 (2)	H12B—C12—H12C	109.00
C1—N1—H29	122 (2)	H12A—C12—H12B	109.00
C1—N2—H2NA	120 (2)	H2WA—O2W—H2WB	109 (3)

O1—C13—C14—O3	−179.57 (18)	C18—C19—C20—O11	−135.1 (2)
O1—C13—C14—C15	57.4 (2)	C18—C19—C20—O12	46.2 (2)
O2—C13—C14—O3	−1.2 (3)	C5—N1—C1—N2	180.0 (2)
O2—C13—C14—C15	−124.3 (2)	C5—N1—C1—C2	−1.1 (3)
O3—C14—C15—O4	−63.3 (2)	C1—N1—C5—C4	0.9 (4)
O3—C14—C15—C16	58.3 (2)	N2—C1—C2—C3	179.0 (2)
C13—C14—C15—O4	59.26 (19)	N1—C1—C2—C3	0.1 (3)
C13—C14—C15—C16	−179.20 (14)	C1—C2—C3—C4	1.2 (3)
O4—C15—C16—O5	−170.89 (18)	C1—C2—C3—C6	−178.3 (2)
O4—C15—C16—O6	10.5 (3)	C6—C3—C4—C5	178.0 (2)
C14—C15—C16—O5	69.1 (2)	C2—C3—C4—C5	−1.4 (3)
C14—C15—C16—O6	−109.5 (2)	C3—C4—C5—N1	0.5 (3)
O7—C17—C18—O9	−173.74 (17)	C11—N3—C7—C8	1.0 (4)
O7—C17—C18—C19	64.6 (2)	C7—N3—C11—N4	179.3 (2)
O8—C17—C18—O9	6.1 (3)	C7—N3—C11—C10	−1.1 (4)
O8—C17—C18—C19	−115.6 (2)	N3—C7—C8—C9	−0.1 (4)
O9—C18—C19—O10	−63.25 (18)	C7—C8—C9—C12	179.5 (3)
O9—C18—C19—C20	59.5 (2)	C7—C8—C9—C10	−0.8 (4)
C17—C18—C19—O10	56.5 (2)	C8—C9—C10—C11	0.7 (3)
C17—C18—C19—C20	179.23 (17)	C12—C9—C10—C11	−179.6 (3)
O10—C19—C20—O11	−14.1 (3)	C9—C10—C11—N4	179.8 (2)
O10—C19—C20—O12	167.13 (16)	C9—C10—C11—N3	0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2	0.87 (3)	1.86 (3)	2.725 (3)	172 (3)
O1W—H1WB···O3ⁱ	0.78 (3)	2.39 (4)	3.012 (3)	137 (3)
O1W—H1WB···O12	0.78 (3)	2.39 (3)	3.006 (3)	137 (3)
O3—H3···O2	0.82 (4)	1.95 (4)	2.562 (2)	131 (4)
O3—H3···O7	0.82 (4)	2.51 (4)	3.072 (3)	127 (3)
N2—H2NA···O1Wⁱⁱ	0.84 (3)	2.00 (3)	2.819 (3)	164 (3)
N3—H3N···O4	0.84 (3)	2.15 (3)	2.939 (3)	157 (3)
N3—H3N···O6	0.84 (3)	2.44 (3)	3.047 (3)	130 (3)
N2—H2NB···O8ⁱⁱⁱ	0.83 (4)	2.41 (3)	3.032 (3)	132 (3)
N2—H2NB···O9ⁱⁱⁱ	0.83 (4)	2.21 (4)	2.942 (3)	147 (3)
O4—H4A···O11^iv	0.90 (4)	1.88 (4)	2.732 (3)	156 (3)
O2W—H2WA···O8ⁱ	0.82 (4)	2.00 (4)	2.819 (3)	173 (4)
O5—H5A···O1ⁱⁱ	1.16 (4)	1.41 (4)	2.534 (2)	163 (4)
N4—H4NA···O3	0.88 (3)	2.12 (3)	2.968 (3)	163 (3)
O7—H7A···O12ⁱⁱ	1.09 (4)	1.39 (4)	2.476 (2)	174 (4)
N4—H4NB···O2Wⁱⁱ	0.83 (4)	2.32 (4)	3.128 (4)	164 (3)
N4—H4NB···O12ⁱⁱ	0.83 (4)	2.60 (4)	2.955 (4)	108 (3)
O9—H9···O2W	0.91 (3)	1.81 (3)	2.715 (3)	172 (3)
O10—H10A···O6^v	0.83 (3)	2.19 (3)	2.912 (3)	145 (3)
O10—H10A···O11	0.83 (3)	2.15 (3)	2.648 (3)	119 (3)
N1—H29···O10ⁱⁱⁱ	0.78 (3)	2.24 (3)	2.946 (3)	151 (3)
C5—H5···O6^vi	0.93	2.46	3.158 (3)	132

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2	0.87 (3)	1.86 (3)	2.725 (3)	172 (3)
O1W—H1WB···O3ⁱ	0.78 (3)	2.39 (4)	3.012 (3)	137 (3)
O1W—H1WB···O12	0.78 (3)	2.39 (3)	3.006 (3)	137 (3)
O3—H3···O2	0.82 (4)	1.95 (4)	2.562 (2)	131 (4)
O3—H3···O7	0.82 (4)	2.51 (4)	3.072 (3)	127 (3)
N2—H2NA···O1Wⁱⁱ	0.84 (3)	2.00 (3)	2.819 (3)	164 (3)
N3—H3N···O4	0.84 (3)	2.15 (3)	2.939 (3)	157 (3)
N3—H3N···O6	0.84 (3)	2.44 (3)	3.047 (3)	130 (3)
N2—H2NB···O8ⁱⁱⁱ	0.83 (4)	2.41 (3)	3.032 (3)	132 (3)
N2—H2NB···O9ⁱⁱⁱ	0.83 (4)	2.21 (4)	2.942 (3)	147 (3)
O4—H4A···O11^iv	0.90 (4)	1.88 (4)	2.732 (3)	156 (3)
O2W—H2WA···O8ⁱ	0.82 (4)	2.00 (4)	2.819 (3)	173 (4)
O5—H5A···O1ⁱⁱ	1.16 (4)	1.41 (4)	2.534 (2)	163 (4)
N4—H4NA···O3	0.88 (3)	2.12 (3)	2.968 (3)	163 (3)
O7—H7A···O12ⁱⁱ	1.09 (4)	1.39 (4)	2.476 (2)	174 (4)
N4—H4NB···O2Wⁱⁱ	0.83 (4)	2.32 (4)	3.128 (4)	164 (3)
N4—H4NB···O12ⁱⁱ	0.83 (4)	2.60 (4)	2.955 (4)	108 (3)
O9—H9···O2W	0.91 (3)	1.81 (3)	2.715 (3)	172 (3)
O10—H10A···O6^v	0.83 (3)	2.19 (3)	2.912 (3)	145 (3)
O10—H10A···O11	0.83 (3)	2.15 (3)	2.648 (3)	119 (3)
N1—H29···O10ⁱⁱⁱ	0.78 (3)	2.24 (3)	2.946 (3)	151 (3)
C5—H5···O6^vi	0.93	2.46	3.158 (3)	132

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

Acknowledgements

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection and computer facilities.

References

Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Schwid, S. B., Petrie, M. D., McDermott, M. P., Tierney, D. S., Mason, D. H. & Goodman, A. D. (1997). Neurology, 48, 817–821. CrossRef CAS PubMed Web of Science Google Scholar
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Volume 70| Part 9| September 2014| Pages o1036-o1037

doi:10.1107/S160053681401842X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 2-amino-4-methyl­pyridin-1-ium (2R,3R)-3-carb­­oxy-2,3-di­hy­droxy­propano­ate monohydrate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 2-amino-4-methylpyridin-1-ium (2R,3R)-3-carboxy-2,3-dihydroxypropanoate monohydrate