Bis[glycinium(0.5+)] perrhenate

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

doi:10.1107/S160053680803849X

metal-organic compounds

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Volume 65| Part 1| January 2009| Page m19

doi:10.1107/S160053680803849X

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Bis[glycinium(0.5+)] perrhenate

V. H. Rodrigues,^a ^* M. M. R. R. Costa,^a T. Dekola ^b and E. de Matos Gomes ^b

^aCEMDRX, Department of Physics, University of Coimbra, P-3004-516 Coimbra, Portugal, and ^bDepartamento de Física, Universidade do Minho, P-4710-057 Braga, Portugal
^*Correspondence e-mail: vhugo@pollux.fis.uc.pt

(Received 29 July 2008; accepted 18 November 2008; online 6 December 2008)

All the residues of the title compound, (C₂H_5.5NO₂)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

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

Experimental

Crystal data

(C₂H_5.5NO₂)₂[ReO₄]
M_r = 401.35
Monoclinic, P 2₁ /c
a = 15.7095 (5) Å
b = 8.1826 (3) Å
c = 8.2909 (3) Å
β = 103.7152 (16)°
V = 1035.36 (6) Å³
Z = 4
Mo Kα radiation
μ = 11.77 mm⁻¹
T = 291 (2) K
0.15 × 0.13 × 0.10 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.18, T_max = 0.31
78826 measured reflections
8587 independent reflections
6232 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.055
S = 1.06
8587 reflections
141 parameters
H-atom parameters constrained
Δρ_max = 2.33 e Å⁻³
Δρ_min = −2.87 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O12—H12⋯O22ⁱ	0.82	1.64	2.445 (2)	167
N11—H11A⋯O11ⁱⁱ	0.89	2.02	2.869 (2)	158
N11—H11B⋯O21	0.89	2.18	3.003 (2)	153
N11—H11B⋯O2	0.89	2.47	3.000 (3)	119
N11—H11C⋯O11ⁱⁱⁱ	0.89	1.94	2.830 (3)	175
O22—H22⋯O12ⁱ	0.82	1.64	2.445 (2)	165
N21—H21A⋯O21	0.89	2.27	2.738 (3)	113
N21—H21A⋯O1	0.89	2.29	3.136 (4)	158
N21—H21B⋯O3^iv	0.89	2.10	2.896 (3)	149
N21—H21B⋯O1^v	0.89	2.60	3.274 (4)	133
N21—H21C⋯O4^vi	0.89	2.14	2.794 (3)	130
N21—H21C⋯O1^vii	0.89	2.37	3.012 (3)	130
Symmetry codes: (i) -x, -y+1, -z; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z; (v) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vi) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker–Nonius, 2004 ); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; 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 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803849X/rn2049sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803849X/rn2049Isup2.hkl

checkCIF report

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.

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

	Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound. Displacement ellipsoids are drawn at the 50% level.
	Fig. 2. Packing of glycine molecules showing the (100) network.

Bis[glycinium(0.5+)] perrhenate top

Crystal data top

2(C₂H_5.5NO₂)[ReO₄]	F(000) = 752
M_r = 401.35	D_x = 2.575 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7839 reflections
a = 15.7095 (5) Å	θ = 4.0–40.1°
b = 8.1826 (3) Å	µ = 11.77 mm⁻¹
c = 8.2909 (3) Å	T = 291 K
β = 103.7152 (16)°	Block, translucent colourless
V = 1035.36 (6) Å³	0.15 × 0.13 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	8587 independent reflections
Radiation source: fine-focus sealed tube	6232 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 45.3°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −30→31
T_min = 0.18, T_max = 0.31	k = −16→15
78826 measured reflections	l = −16→16

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)] = 0.030	H-atom parameters constrained
wR(F²) = 0.055	w = 1/[σ²(F_o²) + (0.001P)² + 2.2865P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.002
8587 reflections	Δρ_max = 2.33 e Å⁻³
141 parameters	Δρ_min = −2.87 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00614 (15)

Crystal data top

2(C₂H_5.5NO₂)[ReO₄]	V = 1035.36 (6) Å³
M_r = 401.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.7095 (5) Å	µ = 11.77 mm⁻¹
b = 8.1826 (3) Å	T = 291 K
c = 8.2909 (3) Å	0.15 × 0.13 × 0.10 mm
β = 103.7152 (16)°

Data collection top

Bruker APEXII diffractometer	8587 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	6232 reflections with I > 2σ(I)
T_min = 0.18, T_max = 0.31	R_int = 0.038
78826 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.055	H-atom parameters constrained
S = 1.06	Δρ_max = 2.33 e Å⁻³
8587 reflections	Δρ_min = −2.87 e Å⁻³
141 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Re1	0.384633 (5)	0.604894 (11)	0.053166 (13)	0.02896 (3)
O1	0.43021 (16)	0.4923 (4)	0.2269 (3)	0.0636 (7)
O2	0.28327 (14)	0.6733 (3)	0.0625 (4)	0.0633 (8)
O3	0.44936 (16)	0.7699 (3)	0.0397 (5)	0.0685 (9)
O4	0.3784 (2)	0.4775 (4)	−0.1121 (3)	0.0698 (8)
O11	0.02851 (12)	0.9119 (2)	0.2663 (2)	0.0343 (4)
O12	−0.02823 (11)	0.7477 (2)	0.0538 (2)	0.0366 (4)
H12	−0.0747	0.7890	0.0614	0.055*	0.50
C11	0.03285 (13)	0.7965 (3)	0.1730 (3)	0.0242 (3)
C12	0.11921 (13)	0.7067 (3)	0.1971 (3)	0.0291 (4)
H12A	0.1608	0.7754	0.1588	0.035*
H12B	0.1424	0.6864	0.3145	0.035*
N11	0.11042 (11)	0.5501 (2)	0.1070 (2)	0.0253 (3)
H11A	0.0761	0.4833	0.1479	0.038*
H11B	0.1631	0.5048	0.1189	0.038*
H11C	0.0868	0.5676	−0.0002	0.038*
O21	0.24920 (12)	0.3008 (2)	0.0961 (3)	0.0409 (4)
O22	0.16419 (12)	0.1024 (3)	−0.0423 (3)	0.0504 (6)
H22	0.1241	0.1641	−0.0353	0.076*	0.50
C21	0.23754 (14)	0.1710 (3)	0.0210 (3)	0.0281 (4)
C22	0.31325 (16)	0.0716 (3)	−0.0074 (4)	0.0373 (5)
H22A	0.3076	−0.0399	0.0286	0.045*
H22B	0.3109	0.0690	−0.1254	0.045*
N21	0.39933 (12)	0.1372 (3)	0.0823 (3)	0.0337 (4)
H21A	0.3923	0.2372	0.1194	0.051*
H21B	0.4351	0.1417	0.0136	0.051*
H21C	0.4224	0.0724	0.1676	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Re1	0.02220 (4)	0.02717 (4)	0.04083 (5)	−0.00013 (3)	0.01407 (3)	−0.00404 (3)
O1	0.0401 (12)	0.093 (2)	0.0524 (14)	−0.0127 (13)	−0.0001 (10)	0.0177 (14)
O2	0.0333 (10)	0.0379 (10)	0.130 (2)	0.0040 (8)	0.0416 (13)	−0.0007 (13)
O3	0.0467 (12)	0.0383 (11)	0.136 (3)	−0.0090 (9)	0.0521 (16)	−0.0019 (14)
O4	0.080 (2)	0.083 (2)	0.0523 (15)	−0.0094 (16)	0.0276 (14)	−0.0268 (14)
O11	0.0309 (7)	0.0398 (9)	0.0320 (8)	0.0054 (7)	0.0069 (6)	−0.0106 (7)
O12	0.0226 (7)	0.0378 (9)	0.0440 (10)	0.0077 (6)	−0.0031 (7)	−0.0144 (7)
C11	0.0206 (7)	0.0270 (8)	0.0257 (9)	0.0011 (6)	0.0068 (6)	−0.0006 (7)
C12	0.0194 (7)	0.0314 (9)	0.0348 (11)	0.0015 (7)	0.0029 (7)	−0.0069 (8)
N11	0.0187 (6)	0.0262 (7)	0.0300 (9)	0.0035 (5)	0.0043 (6)	0.0002 (6)
O21	0.0259 (7)	0.0310 (8)	0.0635 (13)	0.0041 (6)	0.0063 (8)	−0.0144 (8)
O22	0.0219 (7)	0.0475 (11)	0.0747 (15)	0.0057 (7)	−0.0029 (8)	−0.0284 (11)
C21	0.0213 (8)	0.0288 (9)	0.0323 (10)	0.0054 (7)	0.0027 (7)	−0.0034 (8)
C22	0.0254 (9)	0.0429 (13)	0.0417 (13)	0.0092 (9)	0.0043 (9)	−0.0133 (10)
N21	0.0217 (7)	0.0309 (9)	0.0490 (12)	0.0096 (6)	0.0094 (8)	0.0134 (8)

Geometric parameters (Å, º) top

Re1—O4	1.706 (3)	N11—H11B	0.8900
Re1—O2	1.707 (2)	N11—H11C	0.8900
Re1—O3	1.710 (2)	O21—C21	1.223 (3)
Re1—O1	1.717 (3)	O22—C21	1.277 (3)
O11—C11	1.233 (3)	O22—H22	0.8200
O12—C11	1.267 (3)	C21—C22	1.505 (3)
O12—H12	0.8200	C22—N21	1.481 (3)
C11—C12	1.514 (3)	C22—H22A	0.9700
C12—N11	1.473 (3)	C22—H22B	0.9700
C12—H12A	0.9700	N21—H21A	0.8900
C12—H12B	0.9700	N21—H21B	0.8900
N11—H11A	0.8900	N21—H21C	0.8900

O4—Re1—O2	111.10 (15)	C12—N11—H11C	109.5
O4—Re1—O3	110.60 (15)	H11A—N11—H11C	109.5
O2—Re1—O3	108.64 (11)	H11B—N11—H11C	109.5
O4—Re1—O1	106.21 (17)	C21—O22—H22	109.5
O2—Re1—O1	110.24 (14)	O21—C21—O22	127.1 (2)
O3—Re1—O1	110.03 (15)	O21—C21—C22	121.4 (2)
C11—O12—H12	109.5	O22—C21—C22	111.5 (2)
O11—C11—O12	125.87 (19)	N21—C22—C21	112.7 (2)
O11—C11—C12	118.03 (19)	N21—C22—H22A	109.0
O12—C11—C12	116.08 (18)	C21—C22—H22A	109.0
N11—C12—C11	112.44 (17)	N21—C22—H22B	109.0
N11—C12—H12A	109.1	C21—C22—H22B	109.0
C11—C12—H12A	109.1	H22A—C22—H22B	107.8
N11—C12—H12B	109.1	C22—N21—H21A	109.5
C11—C12—H12B	109.1	C22—N21—H21B	109.5
H12A—C12—H12B	107.8	H21A—N21—H21B	109.5
C12—N11—H11A	109.5	C22—N21—H21C	109.5
C12—N11—H11B	109.5	H21A—N21—H21C	109.5
H11A—N11—H11B	109.5	H21B—N21—H21C	109.5

O11—C11—C12—N11	166.3 (2)	O21—C21—C22—N21	7.3 (4)
O12—C11—C12—N11	−15.7 (3)	O22—C21—C22—N21	−172.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O22ⁱ	0.82	1.64	2.445 (2)	167
N11—H11A···O11ⁱⁱ	0.89	2.02	2.869 (2)	158
N11—H11B···O21	0.89	2.18	3.003 (2)	153
N11—H11B···O2	0.89	2.47	3.000 (3)	119
N11—H11C···O11ⁱⁱⁱ	0.89	1.94	2.830 (3)	175
O22—H22···O12ⁱ	0.82	1.64	2.445 (2)	165
N21—H21A···O21	0.89	2.27	2.738 (3)	113
N21—H21A···O1	0.89	2.29	3.136 (4)	158
N21—H21B···O3^iv	0.89	2.10	2.896 (3)	149
N21—H21B···O1^v	0.89	2.60	3.274 (4)	133
N21—H21C···O4^vi	0.89	2.14	2.794 (3)	130
N21—H21C···O1^vii	0.89	2.37	3.012 (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.

Experimental details

Crystal data
Chemical formula	2(C₂H_5.5NO₂)[ReO₄]
M_r	401.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	15.7095 (5), 8.1826 (3), 8.2909 (3)
β (°)	103.7152 (16)
V (Å³)	1035.36 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	11.77
Crystal size (mm)	0.15 × 0.13 × 0.10

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.18, 0.31
No. of measured, independent and observed [I > 2σ(I)] reflections	78826, 8587, 6232
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	1.001

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.055, 1.06
No. of reflections	8587
No. of parameters	141
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.33, −2.87

Computer programs: APEX2 (Bruker–Nonius, 2004), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), ORTEPII (Johnson, 1976), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O22ⁱ	0.82	1.64	2.445 (2)	167.1
N11—H11A···O11ⁱⁱ	0.89	2.02	2.869 (2)	158.0
N11—H11B···O21	0.89	2.18	3.003 (2)	152.5
N11—H11B···O2	0.89	2.47	3.000 (3)	118.6
N11—H11C···O11ⁱⁱⁱ	0.89	1.94	2.830 (3)	174.6
O22—H22···O12ⁱ	0.82	1.64	2.445 (2)	165.0
N21—H21A···O21	0.89	2.27	2.738 (3)	112.6
N21—H21A···O1	0.89	2.29	3.136 (4)	158.3
N21—H21B···O3^iv	0.89	2.10	2.896 (3)	149.1
N21—H21B···O1^v	0.89	2.60	3.274 (4)	132.9
N21—H21C···O4^vi	0.89	2.14	2.794 (3)	129.8
N21—H21C···O1^vii	0.89	2.37	3.012 (3)	129.6

Acknowledgements

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

References

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