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Acta Cryst. (2009). E65, m19    [ doi:10.1107/S160053680803849X ]

Bis[glycinium(0.5+)] perrhenate

V. H. Rodrigues, M. M. R. R. Costa, T. Dekola and E. de Matos Gomes

Abstract top

All the residues of the title compound, (C2H5.5NO2)2[ReO4], are located in general crystallographic positions. The glycine molecules have usual conformations [Rodrigues Matos Beja et al. (2006). Acta Cryst. C62, o71-o72] with the H atom of the carboxylate group half-occupied, thus bearing a formal half-positive charge per molecule. The perrhenate anion has nearly ideal tetrahedral geometry. A large number of strong hydrogen bonds give rise to the overall three-dimensional network. A two-dimensional network, parallel to (100), is made up of strong O-H...O hydrogen bonds with a donor acceptor distance of 2.445 (2) Å. A large number of weaker O-H...O and N-H...O hydrogen bonds consolidates the structure into an overall three-dimensional network.

Related literature top

For a related structure, see: Rodrigues et al. (2006).

Experimental top

Crystals of the monoclinic polymorph of glycinium glycine perrhenate were obtained from a water solution of analytical grade reagents glycine(99.5%) and perrhenic acid solution (65–75% water, 99.5%), purchased from Aldrich, in a 2:1 molar ratio.

Refinement top

The structure was solved by direct methods using SHELXS97. All H atoms were first located on a difference Fourier map; those bonded to C atoms and carboxyl O atoms were placed at idealized positions and refined as riding [C—H=0.97 and 0.98 Å, O—H=0.82 Å, Uiso(H)=1.2Ueq(C) and Uiso(H)=1.5Ueq(O)].

Examination of the crystal structure with PLATON (Spek, 2003) showed that there are no solvent-accessible voids in the crystal lattice.

Computing details top

Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound. Displacement ellipsoids are drawn at the 50% level.
[Figure 2] Fig. 2. Packing of glycine molecules showing the (100) network.
Bis[glycinium(0.5+)] perrhenate top
Crystal data top
2(C2H5.5NO2)[ReO4]F(000) = 752
Mr = 401.35Dx = 2.575 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7839 reflections
a = 15.7095 (5) Åθ = 4.0–40.1°
b = 8.1826 (3) ŵ = 11.77 mm−1
c = 8.2909 (3) ÅT = 291 K
β = 103.7152 (16)°Block, translucent colourless
V = 1035.36 (6) Å30.15 × 0.13 × 0.10 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer		8587 independent reflections
Radiation source: fine-focus sealed tube6232 reflections with I > 2σ(I)
graphiteRint = 0.038
φ and ω scansθmax = 45.3°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −30→31
Tmin = 0.18, Tmax = 0.31k = −16→15
78826 measured reflectionsl = −16→16
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.055 w = 1/[σ2(Fo2) + (0.001P)2 + 2.2865P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
8587 reflectionsΔρmax = 2.33 e Å−3
141 parametersΔρmin = −2.87 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00614 (15)
Crystal data top
2(C2H5.5NO2)[ReO4]V = 1035.36 (6) Å3
Mr = 401.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.7095 (5) ŵ = 11.77 mm−1
b = 8.1826 (3) ÅT = 291 K
c = 8.2909 (3) Å0.15 × 0.13 × 0.10 mm
β = 103.7152 (16)°
Data collection top
Bruker APEXII
diffractometer		6232 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		Rint = 0.038
Tmin = 0.18, Tmax = 0.31θmax = 45.3°
78826 measured reflectionsStandard reflections: 0
8587 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.055Δρmax = 2.33 e Å−3
S = 1.06Δρmin = −2.87 e Å−3
8587 reflectionsAbsolute structure: ?
141 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Re10.384633 (5)0.604894 (11)0.053166 (13)0.02896 (3)
O10.43021 (16)0.4923 (4)0.2269 (3)0.0636 (7)
O20.28327 (14)0.6733 (3)0.0625 (4)0.0633 (8)
O30.44936 (16)0.7699 (3)0.0397 (5)0.0685 (9)
O40.3784 (2)0.4775 (4)−0.1121 (3)0.0698 (8)
O110.02851 (12)0.9119 (2)0.2663 (2)0.0343 (4)
O12−0.02823 (11)0.7477 (2)0.0538 (2)0.0366 (4)
H12−0.07470.78900.06140.055*0.50
C110.03285 (13)0.7965 (3)0.1730 (3)0.0242 (3)
C120.11921 (13)0.7067 (3)0.1971 (3)0.0291 (4)
H12A0.16080.77540.15880.035*
H12B0.14240.68640.31450.035*
N110.11042 (11)0.5501 (2)0.1070 (2)0.0253 (3)
H11A0.07610.48330.14790.038*
H11B0.16310.50480.11890.038*
H11C0.08680.5676−0.00020.038*
O210.24920 (12)0.3008 (2)0.0961 (3)0.0409 (4)
O220.16419 (12)0.1024 (3)−0.0423 (3)0.0504 (6)
H220.12410.1641−0.03530.076*0.50
C210.23754 (14)0.1710 (3)0.0210 (3)0.0281 (4)
C220.31325 (16)0.0716 (3)−0.0074 (4)0.0373 (5)
H22A0.3076−0.03990.02860.045*
H22B0.31090.0690−0.12540.045*
N210.39933 (12)0.1372 (3)0.0823 (3)0.0337 (4)
H21A0.39230.23720.11940.051*
H21B0.43510.14170.01360.051*
H21C0.42240.07240.16760.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.02220 (4)0.02717 (4)0.04083 (5)−0.00013 (3)0.01407 (3)−0.00404 (3)
O10.0401 (12)0.093 (2)0.0524 (14)−0.0127 (13)−0.0001 (10)0.0177 (14)
O20.0333 (10)0.0379 (10)0.130 (2)0.0040 (8)0.0416 (13)−0.0007 (13)
O30.0467 (12)0.0383 (11)0.136 (3)−0.0090 (9)0.0521 (16)−0.0019 (14)
O40.080 (2)0.083 (2)0.0523 (15)−0.0094 (16)0.0276 (14)−0.0268 (14)
O110.0309 (7)0.0398 (9)0.0320 (8)0.0054 (7)0.0069 (6)−0.0106 (7)
O120.0226 (7)0.0378 (9)0.0440 (10)0.0077 (6)−0.0031 (7)−0.0144 (7)
C110.0206 (7)0.0270 (8)0.0257 (9)0.0011 (6)0.0068 (6)−0.0006 (7)
C120.0194 (7)0.0314 (9)0.0348 (11)0.0015 (7)0.0029 (7)−0.0069 (8)
N110.0187 (6)0.0262 (7)0.0300 (9)0.0035 (5)0.0043 (6)0.0002 (6)
O210.0259 (7)0.0310 (8)0.0635 (13)0.0041 (6)0.0063 (8)−0.0144 (8)
O220.0219 (7)0.0475 (11)0.0747 (15)0.0057 (7)−0.0029 (8)−0.0284 (11)
C210.0213 (8)0.0288 (9)0.0323 (10)0.0054 (7)0.0027 (7)−0.0034 (8)
C220.0254 (9)0.0429 (13)0.0417 (13)0.0092 (9)0.0043 (9)−0.0133 (10)
N210.0217 (7)0.0309 (9)0.0490 (12)0.0096 (6)0.0094 (8)0.0134 (8)
Geometric parameters (Å, °) top
Re1—O41.706 (3)N11—H11B0.8900
Re1—O21.707 (2)N11—H11C0.8900
Re1—O31.710 (2)O21—C211.223 (3)
Re1—O11.717 (3)O22—C211.277 (3)
O11—C111.233 (3)O22—H220.8200
O12—C111.267 (3)C21—C221.505 (3)
O12—H120.8200C22—N211.481 (3)
C11—C121.514 (3)C22—H22A0.9700
C12—N111.473 (3)C22—H22B0.9700
C12—H12A0.9700N21—H21A0.8900
C12—H12B0.9700N21—H21B0.8900
N11—H11A0.8900N21—H21C0.8900
O4—Re1—O2111.10 (15)C12—N11—H11C109.5
O4—Re1—O3110.60 (15)H11A—N11—H11C109.5
O2—Re1—O3108.64 (11)H11B—N11—H11C109.5
O4—Re1—O1106.21 (17)C21—O22—H22109.5
O2—Re1—O1110.24 (14)O21—C21—O22127.1 (2)
O3—Re1—O1110.03 (15)O21—C21—C22121.4 (2)
C11—O12—H12109.5O22—C21—C22111.5 (2)
O11—C11—O12125.87 (19)N21—C22—C21112.7 (2)
O11—C11—C12118.03 (19)N21—C22—H22A109.0
O12—C11—C12116.08 (18)C21—C22—H22A109.0
N11—C12—C11112.44 (17)N21—C22—H22B109.0
N11—C12—H12A109.1C21—C22—H22B109.0
C11—C12—H12A109.1H22A—C22—H22B107.8
N11—C12—H12B109.1C22—N21—H21A109.5
C11—C12—H12B109.1C22—N21—H21B109.5
H12A—C12—H12B107.8H21A—N21—H21B109.5
C12—N11—H11A109.5C22—N21—H21C109.5
C12—N11—H11B109.5H21A—N21—H21C109.5
H11A—N11—H11B109.5H21B—N21—H21C109.5
O11—C11—C12—N11166.3 (2)O21—C21—C22—N217.3 (4)
O12—C11—C12—N11−15.7 (3)O22—C21—C22—N21−172.9 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O22i0.821.642.445 (2)167
N11—H11A···O11ii0.892.022.869 (2)158
N11—H11B···O210.892.183.003 (2)153
N11—H11B···O20.892.473.000 (3)119
N11—H11C···O11iii0.891.942.830 (3)175
O22—H22···O12i0.821.642.445 (2)165
N21—H21A···O210.892.272.738 (3)113
N21—H21A···O10.892.293.136 (4)158
N21—H21B···O3iv0.892.102.896 (3)149
N21—H21B···O1v0.892.603.274 (4)133
N21—H21C···O4vi0.892.142.794 (3)130
N21—H21C···O1vii0.892.373.012 (3)130
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, y−1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z; (v) x, −y+1/2, z−1/2; (vi) x, −y+1/2, z+1/2; (vii) −x+1, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O22i0.821.642.445 (2)167
N11—H11A···O11ii0.892.022.869 (2)158
N11—H11B···O210.892.183.003 (2)153
N11—H11B···O20.892.473.000 (3)119
N11—H11C···O11iii0.891.942.830 (3)175
O22—H22···O12i0.821.642.445 (2)165
N21—H21A···O210.892.272.738 (3)113
N21—H21A···O10.892.293.136 (4)158
N21—H21B···O3iv0.892.102.896 (3)149
N21—H21B···O1v0.892.603.274 (4)133
N21—H21C···O4vi0.892.142.794 (3)130
N21—H21C···O1vii0.892.373.012 (3)130
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, y−1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z; (v) x, −y+1/2, z−1/2; (vi) x, −y+1/2, z+1/2; (vii) −x+1, y−1/2, −z+1/2.
Acknowledgements top

This work was supported by Fundação para a Ciência e a Tecnologia (FCT).

references
References top

Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker–Nonius (2004). APEX2. Version 1.0-22. Bruker–Nonius BV, Delft, The Netherlands.

Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.

Rodrigues, V. H., Matos Beja, A., Paixão, J. A. & Costa, M. M. R. R. (2006). Acta Cryst. C62, o71–o72.

Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.