Literature DB >> 21522425

Bis(2-amino-3-carb-oxy-pyrazin-1-ium) sulfate dihydrate.

Fadila Berrah, Amira Ouakkaf, Sofiane Bouacida, Thierry Roisnel.

Abstract

The crystal structure of the title compound, 2C(5)H(6)N(3)O(2) (+)·SO(4) (2-)·2H(2)O, displays a variety of N-H⋯O and O-H⋯O hydrogen bonds in which all potential donors and acceptors are involved. In the crystal, cations and anions are inter-connected, forming R(3) (3)(10) and R(2) (2)(8) ring motifs whereas the anions and water mol-ecules form R(2) (3)(10) rings, which develop in chains running along [100]. The resulting three-dimensional network exhibits undulating sheets parallel to (011), marked by the presence of R(6) (6)(26) rings in which six cations are involved.

Entities: Chemical Disease Species

Year: 2011 PMID： 21522425 PMCID： PMC3052097 DOI： 10.1107/S1600536811005824

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For related compounds, see: Berrah et al. (2005a ▶,b ▶, 2011 ▶); Bouacida et al. (2005 ▶, 2009 ▶); Dobson & Gerkin (1996 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶). For similar intermolecular interactions, see: Dorn et al. (2005 ▶), Janiak (2000 ▶); Desiraju (2003 ▶).

Experimental

Crystal data

2C5H6N3O2 +·SO4 2−·2H2O M = 412.36 Monoclinic, a = 7.7214 (4) Å b = 20.7043 (14) Å c = 10.6398 (7) Å β = 109.299 (2)° V = 1605.36 (17) Å3 Z = 4 Mo Kα radiation μ = 0.27 mm−1 T = 150 K 0.55 × 0.36 × 0.15 mm

Data collection

Bruker APEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.708, T max = 0.960 13466 measured reflections 3675 independent reflections 3146 reflections with I > 2σ(I) R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.096 S = 1.03 3675 reflections 246 parameters H-atom parameters constrained Δρmax = 0.47 e Å−3 Δρmin = −0.48 e Å−3 Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005824/dn2656sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005824/dn2656Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

2C₅H₆N₃O₂⁺·SO₄²⁻·2H₂O	F(000) = 856
M_r = 412.36	D_x = 1.706 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
a = 7.7214 (4) Å	Cell parameters from 5179 reflections
b = 20.7043 (14) Å	θ = 2.8–27.5°
c = 10.6398 (7) Å	µ = 0.27 mm⁻¹
β = 109.299 (2)°	T = 150 K
V = 1605.36 (17) Å³	Prism, yellow
Z = 4	0.55 × 0.36 × 0.15 mm

Bruker APEXII diffractometer	3146 reflections with I > 2σ(I)
graphite	R_int = 0.039
CCD rotation images, thin slices scans	θ_max = 27.6°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −8→9
T_min = 0.708, T_max = 0.960	k = −26→26
13466 measured reflections	l = −13→13
3675 independent reflections

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0491P)² + 0.7394P] where P = (F_o² + 2F_c²)/3
3675 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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.

	x	y	z	U_iso*/U_eq
O5A	0.17659 (16)	0.04617 (6)	0.03501 (11)	0.0221 (3)
H5A	0.1515	0.0732	−0.0273	0.033*
O6A	0.03846 (18)	0.11842 (6)	0.12557 (11)	0.0258 (3)
N1A	0.0567 (2)	0.10587 (7)	0.37979 (13)	0.0231 (3)
H1A1	0.0399	0.1167	0.4549	0.028*
H1A2	0.0122	0.1303	0.3087	0.028*
N2A	0.21592 (19)	0.01604 (6)	0.48490 (13)	0.0195 (3)
H2A	0.1989	0.0288	0.5588	0.023*
N3A	0.27826 (19)	−0.02410 (6)	0.25952 (13)	0.0194 (3)
C1A	0.1266 (2)	0.06905 (7)	0.13275 (15)	0.0185 (3)
C2A	0.1875 (2)	0.02980 (7)	0.25829 (15)	0.0177 (3)
C3A	0.1485 (2)	0.05305 (7)	0.37379 (15)	0.0183 (3)
C4A	0.3079 (2)	−0.03946 (8)	0.48622 (16)	0.0207 (3)
H4A	0.3518	−0.0644	0.5654	0.025*
C5A	0.3374 (2)	−0.05941 (8)	0.37264 (16)	0.0214 (3)
H5C	0.4006	−0.0988	0.3731	0.026*
O5B	−0.03794 (19)	0.32977 (6)	1.37046 (12)	0.0273 (3)
H5B	−0.0768	0.3055	1.4185	0.041*
O6B	−0.03786 (17)	0.23824 (5)	1.25812 (11)	0.0241 (3)
N1B	0.0619 (2)	0.24559 (7)	1.03668 (14)	0.0238 (3)
H1B1	0.0821	0.2313	0.9649	0.029*
H1B2	0.0315	0.2184	1.0895	0.029*
N2B	0.12393 (19)	0.34886 (7)	0.98346 (13)	0.0205 (3)
H2B	0.1422	0.3332	0.912	0.025*
N3B	0.07073 (19)	0.39911 (6)	1.20349 (13)	0.0206 (3)
C1B	−0.0126 (2)	0.29617 (8)	1.27448 (15)	0.0196 (3)
C2B	0.0482 (2)	0.33663 (7)	1.17934 (14)	0.0178 (3)
C3B	0.0773 (2)	0.30786 (8)	1.06522 (15)	0.0187 (3)
C4B	0.1438 (2)	0.41269 (8)	1.00633 (16)	0.0227 (3)
H4B	0.1752	0.4403	0.9458	0.027*
C5B	0.1180 (2)	0.43737 (8)	1.11810 (16)	0.0233 (3)
H5D	0.1338	0.4824	1.1357	0.028*
S1	0.15317 (5)	0.131125 (18)	0.73117 (4)	0.01813 (11)
O1	0.2146 (2)	0.06509 (6)	0.71883 (12)	0.0337 (3)
O2	0.09536 (18)	0.13565 (6)	0.85065 (12)	0.0262 (3)
O3	0.30149 (17)	0.17773 (7)	0.74478 (12)	0.0306 (3)
O4	−0.00482 (16)	0.14708 (6)	0.61180 (11)	0.0236 (3)
O1W	0.23309 (17)	0.30737 (6)	0.78406 (12)	0.0262 (3)
H1W	0.2465	0.2676	0.7697	0.039*
H2W	0.3352	0.3253	0.7903	0.039*
O2W	−0.15818 (19)	0.26453 (6)	1.52193 (12)	0.0296 (3)
H3W	−0.1068	0.2285	1.5511	0.044*
H4W	−0.1653	0.2863	1.5886	0.044*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5A	0.0332 (7)	0.0213 (6)	0.0140 (5)	0.0044 (5)	0.0109 (5)	0.0030 (4)
O6A	0.0400 (7)	0.0206 (6)	0.0184 (6)	0.0076 (5)	0.0115 (5)	0.0036 (4)
N1A	0.0340 (8)	0.0227 (7)	0.0140 (6)	0.0063 (6)	0.0100 (6)	0.0012 (5)
N2A	0.0269 (7)	0.0193 (6)	0.0128 (6)	−0.0002 (5)	0.0072 (5)	0.0001 (5)
N3A	0.0253 (7)	0.0168 (6)	0.0158 (6)	−0.0013 (5)	0.0063 (5)	−0.0003 (5)
C1A	0.0232 (8)	0.0172 (7)	0.0153 (7)	−0.0026 (6)	0.0065 (6)	−0.0007 (6)
C2A	0.0225 (8)	0.0159 (7)	0.0154 (7)	−0.0020 (6)	0.0072 (6)	−0.0008 (6)
C3A	0.0229 (8)	0.0175 (7)	0.0144 (7)	−0.0027 (6)	0.0062 (6)	−0.0007 (6)
C4A	0.0259 (8)	0.0177 (7)	0.0168 (7)	−0.0016 (6)	0.0048 (6)	0.0035 (6)
C5A	0.0279 (9)	0.0163 (7)	0.0186 (7)	0.0011 (6)	0.0056 (6)	0.0000 (6)
O5B	0.0480 (8)	0.0198 (6)	0.0201 (6)	−0.0009 (5)	0.0194 (5)	−0.0004 (5)
O6B	0.0355 (7)	0.0185 (6)	0.0193 (6)	−0.0015 (5)	0.0104 (5)	0.0003 (4)
N1B	0.0372 (8)	0.0188 (7)	0.0167 (6)	−0.0035 (6)	0.0105 (6)	−0.0037 (5)
N2B	0.0267 (7)	0.0221 (7)	0.0128 (6)	−0.0027 (5)	0.0069 (5)	−0.0024 (5)
N3B	0.0267 (7)	0.0172 (6)	0.0167 (6)	0.0005 (5)	0.0056 (5)	−0.0008 (5)
C1B	0.0231 (8)	0.0198 (8)	0.0141 (7)	0.0019 (6)	0.0039 (6)	0.0008 (6)
C2B	0.0216 (8)	0.0173 (7)	0.0127 (7)	0.0005 (6)	0.0033 (6)	0.0001 (5)
C3B	0.0203 (8)	0.0194 (7)	0.0142 (7)	−0.0010 (6)	0.0029 (6)	−0.0014 (6)
C4B	0.0276 (9)	0.0201 (8)	0.0195 (7)	−0.0035 (6)	0.0068 (6)	0.0020 (6)
C5B	0.0324 (9)	0.0177 (7)	0.0193 (7)	−0.0019 (6)	0.0077 (7)	0.0004 (6)
S1	0.0259 (2)	0.01758 (19)	0.01276 (18)	0.00290 (14)	0.00883 (15)	0.00224 (13)
O1	0.0605 (9)	0.0245 (6)	0.0186 (6)	0.0188 (6)	0.0163 (6)	0.0047 (5)
O2	0.0429 (7)	0.0230 (6)	0.0193 (6)	0.0051 (5)	0.0192 (5)	0.0035 (5)
O3	0.0291 (7)	0.0384 (7)	0.0238 (6)	−0.0067 (5)	0.0080 (5)	0.0029 (5)
O4	0.0266 (6)	0.0246 (6)	0.0179 (6)	0.0031 (5)	0.0049 (5)	0.0017 (4)
O1W	0.0294 (6)	0.0273 (6)	0.0252 (6)	−0.0009 (5)	0.0136 (5)	−0.0005 (5)
O2W	0.0460 (8)	0.0244 (6)	0.0229 (6)	0.0086 (5)	0.0174 (6)	0.0061 (5)

O5A—C1A	1.3116 (19)	N1B—H1B1	0.88
O5A—H5A	0.84	N1B—H1B2	0.88
O6A—C1A	1.216 (2)	N2B—C4B	1.343 (2)
N1A—C3A	1.316 (2)	N2B—C3B	1.347 (2)
N1A—H1A1	0.88	N2B—H2B	0.88
N1A—H1A2	0.88	N3B—C2B	1.319 (2)
N2A—C4A	1.349 (2)	N3B—C5B	1.344 (2)
N2A—C3A	1.360 (2)	C1B—C2B	1.503 (2)
N2A—H2A	0.88	C2B—C3B	1.435 (2)
N3A—C2A	1.315 (2)	C4B—C5B	1.368 (2)
N3A—C5A	1.352 (2)	C4B—H4B	0.95
C1A—C2A	1.500 (2)	C5B—H5D	0.95
C2A—C3A	1.442 (2)	S1—O1	1.4670 (12)
C4A—C5A	1.365 (2)	S1—O3	1.4677 (13)
C4A—H4A	0.95	S1—O4	1.4786 (12)
C5A—H5C	0.95	S1—O2	1.4831 (12)
O5B—C1B	1.3028 (19)	O1W—H1W	0.8491
O5B—H5B	0.84	O1W—H2W	0.8542
O6B—C1B	1.218 (2)	O2W—H3W	0.8543
N1B—C3B	1.321 (2)	O2W—H4W	0.8582

C1A—O5A—H5A	109.5	C4B—N2B—C3B	122.81 (14)
C3A—N1A—H1A1	120	C4B—N2B—H2B	118.6
C3A—N1A—H1A2	120	C3B—N2B—H2B	118.6
H1A1—N1A—H1A2	120	C2B—N3B—C5B	119.63 (14)
C4A—N2A—C3A	122.57 (14)	O6B—C1B—O5B	125.38 (15)
C4A—N2A—H2A	118.7	O6B—C1B—C2B	121.55 (14)
C3A—N2A—H2A	118.7	O5B—C1B—C2B	113.05 (14)
C2A—N3A—C5A	119.32 (14)	N3B—C2B—C3B	121.62 (14)
O6A—C1A—O5A	123.99 (14)	N3B—C2B—C1B	117.76 (14)
O6A—C1A—C2A	121.03 (14)	C3B—C2B—C1B	120.62 (14)
O5A—C1A—C2A	114.98 (13)	N1B—C3B—N2B	119.31 (15)
N3A—C2A—C3A	122.39 (14)	N1B—C3B—C2B	124.91 (15)
N3A—C2A—C1A	118.54 (14)	N2B—C3B—C2B	115.78 (14)
C3A—C2A—C1A	119.06 (14)	N2B—C4B—C5B	118.98 (15)
N1A—C3A—N2A	118.94 (14)	N2B—C4B—H4B	120.5
N1A—C3A—C2A	125.91 (14)	C5B—C4B—H4B	120.5
N2A—C3A—C2A	115.15 (14)	N3B—C5B—C4B	121.17 (15)
N2A—C4A—C5A	119.33 (14)	N3B—C5B—H5D	119.4
N2A—C4A—H4A	120.3	C4B—C5B—H5D	119.4
C5A—C4A—H4A	120.3	O1—S1—O3	110.91 (9)
N3A—C5A—C4A	121.21 (15)	O1—S1—O4	109.31 (7)
N3A—C5A—H5C	119.4	O3—S1—O4	109.46 (7)
C4A—C5A—H5C	119.4	O1—S1—O2	109.47 (7)
C1B—O5B—H5B	109.5	O3—S1—O2	108.66 (7)
C3B—N1B—H1B1	120	O4—S1—O2	109.00 (7)
C3B—N1B—H1B2	120	H1W—O1W—H2W	105.7
H1B1—N1B—H1B2	120	H3W—O2W—H4W	108

C5A—N3A—C2A—C3A	0.1 (2)	C5B—N3B—C2B—C3B	1.6 (2)
C5A—N3A—C2A—C1A	178.70 (14)	C5B—N3B—C2B—C1B	−177.43 (14)
O6A—C1A—C2A—N3A	178.18 (15)	O6B—C1B—C2B—N3B	179.35 (15)
O5A—C1A—C2A—N3A	−2.2 (2)	O5B—C1B—C2B—N3B	0.9 (2)
O6A—C1A—C2A—C3A	−3.2 (2)	O6B—C1B—C2B—C3B	0.3 (2)
O5A—C1A—C2A—C3A	176.41 (14)	O5B—C1B—C2B—C3B	−178.12 (14)
C4A—N2A—C3A—N1A	178.56 (15)	C4B—N2B—C3B—N1B	−179.42 (15)
C4A—N2A—C3A—C2A	−1.9 (2)	C4B—N2B—C3B—C2B	0.5 (2)
N3A—C2A—C3A—N1A	−179.04 (16)	N3B—C2B—C3B—N1B	178.17 (15)
C1A—C2A—C3A—N1A	2.4 (2)	C1B—C2B—C3B—N1B	−2.9 (2)
N3A—C2A—C3A—N2A	1.5 (2)	N3B—C2B—C3B—N2B	−1.7 (2)
C1A—C2A—C3A—N2A	−177.09 (13)	C1B—C2B—C3B—N2B	177.27 (14)
C3A—N2A—C4A—C5A	0.8 (2)	C3B—N2B—C4B—C5B	0.8 (2)
C2A—N3A—C5A—C4A	−1.4 (2)	C2B—N3B—C5B—C4B	−0.2 (3)
N2A—C4A—C5A—N3A	0.9 (2)	N2B—C4B—C5B—N3B	−1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A1···O4	0.88	1.92	2.7970 (18)	175.
N1A—H1A2···O6A	0.88	2.04	2.6741 (18)	128.
N1A—H1A2···O6Bⁱ	0.88	2.30	3.0158 (18)	138.
N2A—H2A···O1	0.88	1.83	2.6915 (18)	167.
N1B—H1B1···O2	0.88	2.34	3.0827 (18)	142.
N1B—H1B2···O6B	0.88	2.08	2.7144 (19)	129.
N1B—H1B2···O6Aⁱⁱ	0.88	2.10	2.8237 (18)	139.
N2B—H2B···O1W	0.88	1.81	2.6705 (18)	167.
O5B—H5B···O2W	0.84	1.67	2.5046 (17)	174.
O5A—H5A···O2ⁱ	0.84	1.78	2.6192 (16)	175.
O1W—H1W···O3	0.85	1.95	2.7934 (19)	175.
O1W—H2W···O2ⁱⁱⁱ	0.85	2.06	2.8996 (18)	167
O1W—H2W···O4ⁱⁱⁱ	0.85	2.65	3.2856 (17)	133.
O2W—H3W···O4ⁱⁱ	0.85	1.88	2.7351 (17)	177.
O2W—H4W···O3^iv	0.86	1.91	2.7633 (17)	171.
C4A—H4A···O5B^v	0.95	2.58	3.320 (2)	134.
C4A—H4A···N3B^v	0.95	2.45	3.369 (2)	163.
C4B—H4B···O5A^vi	0.95	2.45	3.187 (2)	134.
C4B—H4B···N3A^vi	0.95	2.44	3.347 (2)	159
C5A—H5C···O1W^vii	0.95	2.55	3.175 (2)	124.
C5B—H5D···O1^viii	0.95	2.35	3.192 (2)	148.

CgI	CgJ	CgI···CgJ^a	α	β	γ	CgI···P(J)^b	CgJ···P(I)^c	Slippage
Cg1	Cg1ⁱ	3.9678 (9)	0	34.94	34.94	3.2528 (6)	3.2527 (6)	2.272

X	I	J	I···J	X–I···J	X···J
S1	O1	Cg1ⁱ	3.5922 (17)	91.83 (7)	3.9233 (8)
S1	O2	Cg1ⁱ	3.9845 (14)	76.88 (5)	3.9233 (8)
S1	O2	Cg2ⁱⁱ	3.8831 (15)	92.77 (6)	4.2231 (8)
C1A	O6A	Cg2ⁱⁱⁱ	3.3136 (16)	125.62 (11)	4.1418 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A1⋯O4	0.88	1.92	2.7970 (18)	175
N1A—H1A2⋯O6A	0.88	2.04	2.6741 (18)	128
N1A—H1A2⋯O6Bⁱ	0.88	2.30	3.0158 (18)	138
N2A—H2A⋯O1	0.88	1.83	2.6915 (18)	167
N1B—H1B1⋯O2	0.88	2.34	3.0827 (18)	142
N1B—H1B2⋯O6B	0.88	2.08	2.7144 (19)	129
N1B—H1B2⋯O6Aⁱⁱ	0.88	2.10	2.8237 (18)	139
N2B—H2B⋯O1W	0.88	1.81	2.6705 (18)	167
O5B—H5B⋯O2W	0.84	1.67	2.5046 (17)	174
O5A—H5A⋯O2ⁱ	0.84	1.78	2.6192 (16)	175
O1W—H1W⋯O3	0.85	1.95	2.7934 (19)	175
O1W—H2W⋯O2ⁱⁱⁱ	0.85	2.06	2.8996 (18)	167
O1W—H2W⋯O4ⁱⁱⁱ	0.85	2.65	3.2856 (17)	133
O2W—H3W⋯O4ⁱⁱ	0.85	1.88	2.7351 (17)	177
O2W—H4W⋯O3^iv	0.86	1.91	2.7633 (17)	171

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

5 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. 3-Aminopyrazine-2-carboxylic acid.

Authors: A J Dobson; R E Gerkin
Journal: Acta Crystallogr C Date: 1996-06-15 Impact factor: 1.172

3. Graph-set analysis of hydrogen-bond patterns in organic crystals.

Authors: M C Etter; J C MacDonald; J Bernstein
Journal: Acta Crystallogr B Date: 1990-04-01

4. 3,4-Dimethyl-anilinium chloride monohydrate.

Authors: Sofiane Bouacida; Ratiba Belhouas; Habiba Kechout; Hocine Merazig; Patricia Bénard-Rocherullé
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-02-28

5. 2-Amino-3-carb-oxy-pyrazin-1-ium nitrate monohydrate.

Authors: Fadila Berrah; Amira Ouakkaf; Sofiane Bouacida; Thierry Roisnel
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-01-29