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metal-organic compounds
Extensive hydrogen-bonding network and an unusual cation conformation in [tris(hydroxymethyl)methyl]ammonium tetraoxidorhenate(VII)
aFaculty of Chemistry, University of Wrocław, 14 Joliot-Curie St, 50-383 Wrocław, Poland
*Correspondence e-mail: holynska@wcheto.chem.uni.wroc.pl
The title compound, (C4H12NO3)[ReO4], contains two cations and two anions in the related by a non-crystallographic centre of symmetry. The is stabilized by an extensive hydrogen-bonding network with the formation of puckered layers perpendicular to [001]. In the tris(hydroxymethyl)ammonium cations, intramolecular O—H⋯O hydrogen bonds are present with the formation of an S11(6) graph-set motif. The is further consolidated by N—H⋯O hydrogen bonds.
Related literature
For related structures, see: Castellari & Ottani (1997); Eilerman & Rudman (1980
); Hołyńska & Lis (2004
, 2008
); Lock & Turner (1975
); Marsh et al. (1998
); Rudman et al. (1979
, 1983
); Shakked et al. (1980
); Tusvik et al. (1999
). For the dielectric properties of rhenates(VII) with organic ammonium cations, see: Czarnecki & Małuszyńska (2000
). For graph-set notation, see: Etter et al. (1990
). For the synthesis of rhenic(VII) acid, see: Johnson et al. (1967
).
Experimental
Crystal data
|
Refinement
|
|
|
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell CrysAlis RED (Oxford Diffraction, 2006
); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: DIAMOND (Brandenburg & Putz, 2005
) and SHELXTL-NT (Sheldrick, 2008
); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536809028797/ez2176sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809028797/ez2176Isup2.hkl
The title compound was obtained in the reaction of 0.19 g of tris(hydroxymethyl)methylamine (TRIS) with an excess of rhenic(VII) acid in aqueous solution, with slow evaporation leading to colourless crystals. The reaction was carried out in a quartz beaker. Rhenic(VII) acid was obtained according to the literature procedure (Johnson et al., 1967) in reaction of 0.3 g of metallic Re with an excess of a 30% aqueous hydrogen peroxide solution.
The structure was solved by
in the P1, and the present solution was obtained by switching to a higher symmetry. It was possible to end up in a false minimum in the Pca21 (e.g. with the following approximate coordinates for the Re atoms: 0.57, 0.024, 0.97 for Re1; 0.69, 0.51, 1.01 for Re2; see Marsh et al., 1998, for a review of some pitfalls connected with the Pca21 space group). All H atoms were generated geometrically and refined with Ueq=nUeq(parent atom), where n = 1.5 for hydroxyl H atoms, and n = 1.2 for the remaining H atoms. During the extinction was also taken into account. Furthermore, it was found that the structure is a racemic twin (with a refined BASF parameter value of 0.375 (6)). On the final difference Fourier map the highest peak of 2.00 e/Å3 was found at 0.62 Å from atom Re2. The contains a centre at approximately (0.37, 0.73, 0.38).Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell
CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005) and SHELXTL-NT (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).(C4H12NO3)[ReO4] | F(000) = 1392 |
Mr = 372.35 | Dx = 2.748 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 20472 reflections |
a = 21.450 (5) Å | θ = 4.2–35.0° |
b = 6.867 (2) Å | µ = 13.51 mm−1 |
c = 12.219 (4) Å | T = 110 K |
V = 1799.8 (9) Å3 | Needle, colourless |
Z = 8 | 0.21 × 0.16 × 0.14 mm |
Oxford Diffraction KM-4-CCD diffractometer | 5888 independent reflections |
Radiation source: fine-focus sealed tube | 5084 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 35.0°, θmin = 4.2° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006) | h = −33→28 |
Tmin = 0.104, Tmax = 0.268 | k = −9→11 |
24604 measured reflections | l = −14→19 |
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)] = 0.020 | H-atom parameters constrained |
wR(F2) = 0.034 | w = 1/[σ2(Fo2) + (0.0119P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.002 |
5888 reflections | Δρmax = 2.00 e Å−3 |
245 parameters | Δρmin = −1.27 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00101 (3) |
(C4H12NO3)[ReO4] | V = 1799.8 (9) Å3 |
Mr = 372.35 | Z = 8 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 21.450 (5) Å | µ = 13.51 mm−1 |
b = 6.867 (2) Å | T = 110 K |
c = 12.219 (4) Å | 0.21 × 0.16 × 0.14 mm |
Oxford Diffraction KM-4-CCD diffractometer | 5888 independent reflections |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006) | 5084 reflections with I > 2σ(I) |
Tmin = 0.104, Tmax = 0.268 | Rint = 0.029 |
24604 measured reflections |
R[F2 > 2σ(F2)] = 0.020 | 1 restraint |
wR(F2) = 0.034 | H-atom parameters constrained |
S = 1.02 | Δρmax = 2.00 e Å−3 |
5888 reflections | Δρmin = −1.27 e Å−3 |
245 parameters |
x | y | z | Uiso*/Ueq | ||
Re1 | 0.311748 (6) | 0.494021 (19) | 0.362409 (13) | 0.01257 (4) | |
O11 | 0.38162 (12) | 0.5562 (4) | 0.2998 (2) | 0.0266 (6) | |
O21 | 0.29045 (12) | 0.2623 (3) | 0.3220 (2) | 0.0217 (6) | |
O31 | 0.25389 (12) | 0.6547 (3) | 0.3237 (2) | 0.0204 (6) | |
O41 | 0.31950 (13) | 0.4971 (3) | 0.5010 (4) | 0.0192 (7) | |
Re2 | 0.431704 (6) | 0.975939 (17) | 0.393938 (10) | 0.01252 (4) | |
O12 | 0.43101 (13) | 0.9629 (4) | 0.2527 (4) | 0.0201 (7) | |
O22 | 0.48425 (12) | 0.8084 (4) | 0.4456 (2) | 0.0239 (6) | |
O32 | 0.35819 (12) | 0.9281 (4) | 0.4468 (2) | 0.0236 (6) | |
O42 | 0.45440 (14) | 1.2076 (3) | 0.4316 (2) | 0.0256 (6) | |
N1 | 0.54415 (13) | 0.4794 (3) | 0.3475 (3) | 0.0087 (7) | |
H1A | 0.5752 | 0.4330 | 0.3909 | 0.010* | |
H1B | 0.5116 | 0.3943 | 0.3478 | 0.010* | |
H1C | 0.5312 | 0.5969 | 0.3733 | 0.010* | |
C1 | 0.56824 (16) | 0.5031 (4) | 0.2313 (5) | 0.0108 (9) | |
C11 | 0.62070 (17) | 0.6555 (5) | 0.2341 (3) | 0.0158 (8) | |
H11A | 0.6583 | 0.5969 | 0.2674 | 0.019* | |
H11B | 0.6313 | 0.6942 | 0.1582 | 0.019* | |
O111 | 0.60331 (12) | 0.8244 (3) | 0.2949 (2) | 0.0161 (5) | |
H111 | 0.5882 | 0.9079 | 0.2523 | 0.024* | |
C21 | 0.59498 (17) | 0.3079 (5) | 0.1935 (3) | 0.0161 (8) | |
H21A | 0.6055 | 0.3169 | 0.1148 | 0.019* | |
H21B | 0.6341 | 0.2820 | 0.2340 | 0.019* | |
O211 | 0.55315 (12) | 0.1482 (3) | 0.2097 (2) | 0.0190 (6) | |
H211 | 0.5192 | 0.1715 | 0.1780 | 0.029* | |
C31 | 0.51492 (18) | 0.5698 (6) | 0.1573 (3) | 0.0171 (8) | |
H31A | 0.4977 | 0.6936 | 0.1858 | 0.020* | |
H31B | 0.5313 | 0.5947 | 0.0829 | 0.020* | |
O311 | 0.46638 (12) | 0.4291 (4) | 0.1512 (2) | 0.0194 (6) | |
H311 | 0.4369 | 0.4628 | 0.1922 | 0.029* | |
N2 | 0.19985 (14) | 0.0038 (3) | 0.4133 (3) | 0.0106 (7) | |
H2A | 0.2325 | 0.0881 | 0.4100 | 0.013* | |
H2B | 0.1679 | 0.0501 | 0.3718 | 0.013* | |
H2C | 0.2120 | −0.1145 | 0.3873 | 0.013* | |
C2 | 0.17844 (17) | −0.0169 (5) | 0.5312 (5) | 0.0126 (9) | |
C12 | 0.15266 (17) | 0.1803 (5) | 0.5682 (3) | 0.0141 (7) | |
H12A | 0.1130 | 0.2060 | 0.5295 | 0.017* | |
H12B | 0.1436 | 0.1749 | 0.6476 | 0.017* | |
O112 | 0.19500 (12) | 0.3372 (3) | 0.5474 (2) | 0.0174 (6) | |
H112 | 0.2293 | 0.3138 | 0.5778 | 0.026* | |
C22 | 0.23218 (16) | −0.0833 (5) | 0.6035 (3) | 0.0150 (7) | |
H22A | 0.2164 | −0.1076 | 0.6784 | 0.018* | |
H22B | 0.2489 | −0.2075 | 0.5748 | 0.018* | |
O212 | 0.28111 (11) | 0.0562 (4) | 0.6084 (2) | 0.0205 (6) | |
H212 | 0.3083 | 0.0288 | 0.5614 | 0.031* | |
C32 | 0.12571 (16) | −0.1669 (5) | 0.5331 (3) | 0.0139 (7) | |
H32A | 0.1175 | −0.2067 | 0.6096 | 0.017* | |
H32B | 0.0872 | −0.1067 | 0.5038 | 0.017* | |
O312 | 0.14087 (12) | −0.3355 (3) | 0.4693 (2) | 0.0149 (5) | |
H312 | 0.1612 | −0.4143 | 0.5080 | 0.022* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Re1 | 0.01274 (6) | 0.01028 (5) | 0.01470 (9) | −0.00034 (4) | 0.00299 (6) | 0.00074 (6) |
O11 | 0.0195 (15) | 0.0232 (14) | 0.0373 (17) | −0.0036 (11) | 0.0120 (13) | −0.0001 (13) |
O21 | 0.0299 (16) | 0.0150 (12) | 0.0201 (14) | −0.0036 (10) | 0.0061 (12) | 0.0004 (10) |
O31 | 0.0252 (15) | 0.0141 (12) | 0.0218 (14) | 0.0036 (10) | 0.0011 (12) | −0.0006 (10) |
O41 | 0.0268 (17) | 0.0171 (14) | 0.0137 (18) | −0.0031 (10) | −0.0014 (13) | 0.0013 (11) |
Re2 | 0.01365 (7) | 0.01088 (5) | 0.01303 (8) | −0.00034 (5) | 0.00093 (6) | −0.00031 (8) |
O12 | 0.0235 (16) | 0.0188 (12) | 0.0180 (18) | −0.0037 (11) | −0.0066 (12) | −0.0068 (13) |
O22 | 0.0284 (16) | 0.0237 (14) | 0.0195 (14) | 0.0086 (11) | 0.0016 (12) | 0.0010 (11) |
O32 | 0.0176 (14) | 0.0194 (13) | 0.0336 (15) | −0.0005 (10) | 0.0063 (11) | 0.0011 (12) |
O42 | 0.0393 (17) | 0.0163 (12) | 0.0210 (15) | −0.0084 (11) | 0.0083 (12) | −0.0057 (10) |
N1 | 0.0087 (13) | 0.0032 (10) | 0.014 (2) | −0.0006 (9) | 0.0076 (14) | 0.0021 (11) |
C1 | 0.0109 (18) | 0.0078 (15) | 0.014 (3) | −0.0007 (13) | 0.0004 (14) | 0.0006 (11) |
C11 | 0.0146 (19) | 0.0104 (16) | 0.022 (2) | −0.0019 (13) | 0.0032 (15) | −0.0018 (14) |
O111 | 0.0204 (14) | 0.0121 (12) | 0.0158 (13) | −0.0001 (10) | 0.0032 (11) | −0.0008 (9) |
C21 | 0.0166 (19) | 0.0093 (16) | 0.022 (2) | −0.0026 (13) | 0.0030 (16) | −0.0016 (14) |
O211 | 0.0208 (15) | 0.0106 (11) | 0.0256 (16) | −0.0020 (10) | −0.0012 (12) | 0.0010 (11) |
C31 | 0.016 (2) | 0.0167 (19) | 0.018 (2) | 0.0009 (15) | 0.0001 (15) | 0.0032 (15) |
O311 | 0.0127 (14) | 0.0207 (14) | 0.0250 (16) | −0.0001 (11) | −0.0028 (12) | −0.0077 (12) |
N2 | 0.0144 (13) | 0.0044 (12) | 0.013 (2) | 0.0016 (9) | −0.0018 (13) | −0.0049 (10) |
C2 | 0.019 (2) | 0.0092 (17) | 0.010 (2) | 0.0024 (12) | 0.0001 (15) | −0.0013 (13) |
C12 | 0.0154 (19) | 0.0093 (15) | 0.0176 (19) | 0.0010 (12) | 0.0031 (14) | −0.0003 (13) |
O112 | 0.0152 (14) | 0.0083 (11) | 0.0287 (16) | −0.0024 (10) | −0.0020 (12) | −0.0010 (10) |
C22 | 0.0139 (19) | 0.0131 (16) | 0.0182 (19) | 0.0004 (12) | −0.0014 (14) | 0.0007 (14) |
O212 | 0.0124 (14) | 0.0215 (13) | 0.0276 (16) | −0.0009 (10) | −0.0023 (11) | −0.0056 (12) |
C32 | 0.0139 (19) | 0.0098 (16) | 0.018 (2) | −0.0037 (12) | 0.0023 (15) | −0.0022 (13) |
O312 | 0.0173 (14) | 0.0093 (11) | 0.0182 (14) | 0.0009 (9) | −0.0011 (11) | −0.0013 (9) |
Re1—O11 | 1.736 (2) | C31—O311 | 1.423 (4) |
Re1—O21 | 1.728 (2) | C31—H31A | 0.9900 |
Re1—O31 | 1.727 (2) | C31—H31B | 0.9900 |
Re1—O41 | 1.702 (5) | O311—H311 | 0.8400 |
Re2—O12 | 1.728 (4) | N2—C2 | 1.519 (7) |
Re2—O22 | 1.730 (3) | N2—H2A | 0.9100 |
Re2—O32 | 1.736 (3) | N2—H2B | 0.9100 |
Re2—O42 | 1.726 (2) | N2—H2C | 0.9100 |
N1—C1 | 1.520 (7) | C2—C22 | 1.522 (6) |
N1—H1A | 0.9100 | C2—C32 | 1.530 (5) |
N1—H1B | 0.9100 | C2—C12 | 1.531 (5) |
N1—H1C | 0.9100 | C12—O112 | 1.432 (4) |
C1—C31 | 1.528 (6) | C12—H12A | 0.9900 |
C1—C21 | 1.529 (5) | C12—H12B | 0.9900 |
C1—C11 | 1.537 (4) | O112—H112 | 0.8400 |
C11—O111 | 1.427 (4) | C22—O212 | 1.422 (4) |
C11—H11A | 0.9900 | C22—H22A | 0.9900 |
C11—H11B | 0.9900 | C22—H22B | 0.9900 |
O111—H111 | 0.8400 | O212—H212 | 0.8400 |
C21—O211 | 1.431 (4) | C32—O312 | 1.433 (4) |
C21—H21A | 0.9900 | C32—H32A | 0.9900 |
C21—H21B | 0.9900 | C32—H32B | 0.9900 |
O211—H211 | 0.8400 | O312—H312 | 0.8400 |
O41—Re1—O31 | 109.6 (2) | O311—C31—H31A | 109.2 |
O41—Re1—O21 | 108.7 (2) | C1—C31—H31A | 109.2 |
O31—Re1—O21 | 108.7 (2) | O311—C31—H31B | 109.2 |
O41—Re1—O11 | 110.6 (2) | C1—C31—H31B | 109.2 |
O31—Re1—O11 | 110.0 (2) | H31A—C31—H31B | 107.9 |
O21—Re1—O11 | 109.2 (2) | C31—O311—H311 | 109.5 |
O42—Re2—O12 | 108.4 (2) | C2—N2—H2A | 109.5 |
O42—Re2—O22 | 109.4 (2) | C2—N2—H2B | 109.5 |
O12—Re2—O22 | 109.6 (2) | H2A—N2—H2B | 109.5 |
O42—Re2—O32 | 109.3 (2) | C2—N2—H2C | 109.5 |
O12—Re2—O32 | 110.8 (2) | H2A—N2—H2C | 109.5 |
O22—Re2—O32 | 109.3 (2) | H2B—N2—H2C | 109.5 |
C1—N1—H1A | 109.5 | N2—C2—C22 | 110.5 (3) |
C1—N1—H1B | 109.5 | N2—C2—C32 | 107.5 (4) |
H1A—N1—H1B | 109.5 | C22—C2—C32 | 110.5 (3) |
C1—N1—H1C | 109.5 | N2—C2—C12 | 107.8 (3) |
H1A—N1—H1C | 109.5 | C22—C2—C12 | 111.5 (4) |
H1B—N1—H1C | 109.5 | C32—C2—C12 | 108.9 (3) |
N1—C1—C31 | 109.3 (3) | O112—C12—C2 | 112.6 (3) |
N1—C1—C21 | 108.4 (3) | O112—C12—H12A | 109.1 |
C31—C1—C21 | 111.4 (4) | C2—C12—H12A | 109.1 |
N1—C1—C11 | 107.5 (4) | O112—C12—H12B | 109.1 |
C31—C1—C11 | 110.9 (3) | C2—C12—H12B | 109.1 |
C21—C1—C11 | 109.2 (3) | H12A—C12—H12B | 107.8 |
O111—C11—C1 | 111.9 (3) | C12—O112—H112 | 109.5 |
O111—C11—H11A | 109.2 | O212—C22—C2 | 112.4 (3) |
C1—C11—H11A | 109.2 | O212—C22—H22A | 109.1 |
O111—C11—H11B | 109.2 | C2—C22—H22A | 109.1 |
C1—C11—H11B | 109.2 | O212—C22—H22B | 109.1 |
H11A—C11—H11B | 107.9 | C2—C22—H22B | 109.1 |
C11—O111—H111 | 109.5 | H22A—C22—H22B | 107.8 |
O211—C21—C1 | 113.3 (3) | C22—O212—H212 | 109.5 |
O211—C21—H21A | 108.9 | O312—C32—C2 | 111.6 (3) |
C1—C21—H21A | 108.9 | O312—C32—H32A | 109.3 |
O211—C21—H21B | 108.9 | C2—C32—H32A | 109.3 |
C1—C21—H21B | 108.9 | O312—C32—H32B | 109.3 |
H21A—C21—H21B | 107.7 | C2—C32—H32B | 109.3 |
C21—O211—H211 | 109.5 | H32A—C32—H32B | 108.0 |
O311—C31—C1 | 112.0 (3) | C32—O312—H312 | 109.5 |
N1—C1—C11—O111 | −47.2 (4) | N2—C2—C12—O112 | −51.4 (4) |
N1—C1—C21—O211 | 51.0 (4) | N2—C2—C22—O212 | 64.0 (4) |
N1—C1—C31—O311 | −63.1 (4) | N2—C2—C32—O312 | 45.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O21 | 0.91 | 2.03 | 2.858 (4) | 150 |
N2—H2B···O111i | 0.91 | 1.88 | 2.788 (4) | 173 |
N2—H2C···O31ii | 0.91 | 1.98 | 2.879 (4) | 169 |
O112—H112···O212 | 0.84 | 2.12 | 2.773 (4) | 134 |
O112—H112···O41 | 0.84 | 2.49 | 2.942 (4) | 115 |
O212—H212···O32ii | 0.84 | 1.89 | 2.721 (4) | 168 |
O312—H312···O112ii | 0.84 | 1.92 | 2.704 (4) | 156 |
N1—H1A···O312iii | 0.91 | 1.83 | 2.738 (4) | 176 |
N1—H1B···O42ii | 0.91 | 2.05 | 2.872 (4) | 150 |
N1—H1C···O22 | 0.91 | 1.98 | 2.862 (4) | 164 |
O111—H111···O211iv | 0.84 | 1.89 | 2.681 (3) | 157 |
O211—H211···O311 | 0.84 | 2.13 | 2.774 (4) | 134 |
O211—H211···O12ii | 0.84 | 2.54 | 2.960 (4) | 112 |
O311—H311···O11 | 0.84 | 1.88 | 2.714 (4) | 170 |
Symmetry codes: (i) x−1/2, −y+1, z; (ii) x, y−1, z; (iii) x+1/2, −y, z; (iv) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | (C4H12NO3)[ReO4] |
Mr | 372.35 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 110 |
a, b, c (Å) | 21.450 (5), 6.867 (2), 12.219 (4) |
V (Å3) | 1799.8 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 13.51 |
Crystal size (mm) | 0.21 × 0.16 × 0.14 |
Data collection | |
Diffractometer | Oxford Diffraction KM-4-CCD diffractometer |
Absorption correction | Analytical (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.104, 0.268 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24604, 5888, 5084 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.807 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.020, 0.034, 1.02 |
No. of reflections | 5888 |
No. of parameters | 245 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.00, −1.27 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005) and SHELXTL-NT (Sheldrick, 2008).
Re1—O11 | 1.736 (2) | Re2—O12 | 1.728 (4) |
Re1—O21 | 1.728 (2) | Re2—O22 | 1.730 (3) |
Re1—O31 | 1.727 (2) | Re2—O32 | 1.736 (3) |
Re1—O41 | 1.702 (5) | Re2—O42 | 1.726 (2) |
O41—Re1—O31 | 109.6 (2) | O42—Re2—O12 | 108.4 (2) |
O41—Re1—O21 | 108.7 (2) | O42—Re2—O22 | 109.4 (2) |
O31—Re1—O21 | 108.7 (2) | O12—Re2—O22 | 109.6 (2) |
O41—Re1—O11 | 110.6 (2) | O42—Re2—O32 | 109.3 (2) |
O31—Re1—O11 | 110.0 (2) | O12—Re2—O32 | 110.8 (2) |
O21—Re1—O11 | 109.2 (2) | O22—Re2—O32 | 109.3 (2) |
N1—C1—C11—O111 | −47.2 (4) | N2—C2—C12—O112 | −51.4 (4) |
N1—C1—C21—O211 | 51.0 (4) | N2—C2—C22—O212 | 64.0 (4) |
N1—C1—C31—O311 | −63.1 (4) | N2—C2—C32—O312 | 45.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O21 | 0.91 | 2.03 | 2.858 (4) | 150 |
N2—H2B···O111i | 0.91 | 1.88 | 2.788 (4) | 173 |
N2—H2C···O31ii | 0.91 | 1.98 | 2.879 (4) | 169 |
O112—H112···O212 | 0.84 | 2.12 | 2.773 (4) | 134 |
O112—H112···O41 | 0.84 | 2.49 | 2.942 (4) | 115 |
O212—H212···O32ii | 0.84 | 1.89 | 2.721 (4) | 168 |
O312—H312···O112ii | 0.84 | 1.92 | 2.704 (4) | 156 |
N1—H1A···O312iii | 0.91 | 1.83 | 2.738 (4) | 176 |
N1—H1B···O42ii | 0.91 | 2.05 | 2.872 (4) | 150 |
N1—H1C···O22 | 0.91 | 1.98 | 2.862 (4) | 164 |
O111—H111···O211iv | 0.84 | 1.89 | 2.681 (3) | 157 |
O211—H211···O311 | 0.84 | 2.13 | 2.774 (4) | 134 |
O211—H211···O12ii | 0.84 | 2.54 | 2.960 (4) | 112 |
O311—H311···O11 | 0.84 | 1.88 | 2.714 (4) | 170 |
Symmetry codes: (i) x−1/2, −y+1, z; (ii) x, y−1, z; (iii) x+1/2, −y, z; (iv) x, y+1, z. |
Acknowledgements
Financial support from the Ministry of Science and Higher Education (project No. N204 130 32/3318) is acknowledged.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound was obtained as starting material for other syntheses (e.g. reaction with acethyl chloride - Hołyńska & Lis, 2008). It was chosen as the tris(hydroxymethyl)methylammonium cation gives rise to an extensive hydrogen bonding network, which allows for selective crystallization of products containing Re, reducing the risk of cocrystallization of impurities and crystal structure disorder. Moreover, rhenates(VII) with organic ammonium cations crystallizing in non-centrosymmetric space groups are promising materials with respect to their dielectric properties. For example, the previously discovered ferroelectric with a Curie temperature above room temperature is pyridinium rhenate(VII) (Czarnecki & Małuszyńska, 2000).
The title compound (1) is a product of the reaction of rhenic(VII) acid with tris(hydroxymethyl)methylamine (TRIS) in aqueous solution, comprising discrete tris(hydroxymethyl)methylammonium cations (protonated TRIS here denoted as TRISH+) and rhenate(VII) anions (Fig. 1, Scheme 1).
There are two symmetry-independent rhenate(VII) anions (containing atoms Re1 and Re2, respectively) with the expected (see e.g. Hołyńska & Lis, 2004 for example of rhenate(VII) anions in low symmetry environment) slightly distorted tetrahedral geometry. The Re—O bond lengths are listed in Table 1. Their values are consistent with those for other rhenates(VII), e.g. 1.723 (4) Å for potassium rhenate(VII) reported by Lock & Turner (1975). These bond lengths are not much affected by the presence of hydrogen bonds, as all rhenate(VII) O atoms participate in these interactions as acceptors (Table 2).
It is interesting to note that both symmetry-independent TRISH+ cations are of unusual conformation. Usually the cation symmetry is close to C3 (e.g. Rudman et al., 1983) or even exactly threefold (as in [TRISH]Cl appearing in a preliminary report by Rudman et al., 1979) with no intramolecular hydrogen bonds. In (1) both cations exhibit the presence of such intramolecular hydrogen bond (Table 2) with the formation of a S11(6) graph-set motif (Etter et al., 1990). The relevant N—C—C—O torsion angles are given in Table 1. Bond lengths characterizing the cations, among them the C—N bond length (which is longer than in the TRIS molecule - 1.477 (3) Å as reported for the neutral TRIS molecule by Eilerman & Rudman, 1980) are in accordance with the values reported for other structures (e.g. Castellari & Ottani, 1997). TRIS is a constituent of buffers used in biochemical studies in the pH range of 7–9 (Castellari & Ottani, 1997). Upon protonation it forms salts with biologically relevant anions (e.g. tris(hydroxymethyl)methylammonium deoxycholate reported by Tusvik et al., 1999), also a report on its interaction with nucleotides in the crystalline state is available (Shakked et al., 1980).
All cation ammonium and hydroxyl groups are donors in N—H···O or O—H···O hydrogen bonds, both to other TRISH+ cations or to rhenate(VII) anions. The shortest Re···Re distance is 4.210 (2) Å. Thus, puckered hydrogen-bonded layers perpendicular to [001] are formed (Fig. 2). The hydrogen bonding scheme stabilizing an individual layer is illustrated in Fig. 3.