Acta Cryst. (2007). E63, m2355 [ doi:10.1107/S1600536807039608 ]
The title salt, (C4H10NO)[ReO4], contains slightly distorted tetrahedral [ReO4]- anions [Re-O = 1.7224 (11)-1.7361 (11) Å]. The structure consists of alternating cationic and anionic layers parallel to (100). The cations and anions are linked by N-H
O hydrogen bonds into chains along [100].
Synthesis of (I) was carried out as a neutralization reaction by dissolution of morpholine under intensive stirring in 0.2 M water solution of HReO4 at room temperature to achieve pH = 7, followed by evaporation of the resulting solution over concentrated H2SO4. The compound was recrystallized from ethanol.
The H atoms of NH2 and CH2 groups were refined in idealized geometrical positions with displacement parameters being equal to 1.2 times Ueq of the attached N or C atoms.
Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
![[Figure 1]](./ng2306fig1thm.gif)
| Fig. 1. A view of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented by circles of arbitrary size. Dashed line indicates the hydrogen-bonding interaction. |
![[Figure 2]](./ng2306fig2thm.gif)
| Fig. 2. The packing of (I) showing chains of hydrogen bonds. |
| (C4H10NO)[Re1O4] | F000 = 624 |
| Mr = 338.33 | Dx = 2.838 Mg m−3 |
| Orthorhombic, Pca21 | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: P 2c -2ac | Cell parameters from 7854 reflections |
| a = 12.4401 (3) Å | θ = 3.3–35.0º |
| b = 5.7480 (2) Å | µ = 15.37 mm−1 |
| c = 11.0420 (3) Å | T = 100 (2) K |
| V = 789.57 (4) Å3 | Fragment, colourless |
| Z = 4 | 0.16 × 0.12 × 0.10 mm |
| Bruker Kappa APEX II area-detector diffractometer | 3460 independent reflections |
| Radiation source: fine-focus sealed tube | 3315 reflections with I > 2α(I) |
| Monochromator: graphite | Rint = 0.021 |
| T = 100(2) K | θmax = 35.0º |
| ω and φ scans | θmin = 3.3º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −20→19 |
| Tmin = 0.239, Tmax = 0.309 | k = −9→9 |
| 21183 measured reflections | l = −17→17 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.010 | w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.020 | (Δ/σ)max = 0.001 |
| S = 0.94 | Δρmax = 0.70 e Å−3 |
| 3460 reflections | Δρmin = −0.60 e Å−3 |
| 101 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 1 restraint | Extinction coefficient: 0.00092 (6) |
| Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 1650 Friedel pairs |
| Secondary atom site location: difference Fourier map | Flack parameter: 0.004 (4) |
| (C4H10NO)[Re1O4] | V = 789.57 (4) Å3 |
| Mr = 338.33 | Z = 4 |
| Orthorhombic, Pca21 | Mo Kα |
| a = 12.4401 (3) Å | µ = 15.37 mm−1 |
| b = 5.7480 (2) Å | T = 100 (2) K |
| c = 11.0420 (3) Å | 0.16 × 0.12 × 0.10 mm |
| Bruker Kappa APEX II area-detector diffractometer | 3460 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 3315 reflections with I > 2α(I) |
| Tmin = 0.239, Tmax = 0.309 | Rint = 0.021 |
| 21183 measured reflections |
| R[F2 > 2σ(F2)] = 0.010 | H-atom parameters constrained |
| wR(F2) = 0.020 | Δρmax = 0.70 e Å−3 |
| S = 0.94 | Δρmin = −0.60 e Å−3 |
| 3460 reflections | Absolute structure: Flack (1983), with 1650 Friedel pairs |
| 101 parameters | Flack parameter: 0.004 (4) |
| 1 restraint |
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 > 2sigma(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 | Uiso*/Ueq | ||
| Re1 | 0.733624 (3) | 0.804729 (7) | 0.201310 (9) | 0.00950 (2) | |
| O1 | 0.62050 (9) | 0.9089 (2) | 0.27573 (10) | 0.0162 (2) | |
| O2 | 0.75192 (9) | 0.5155 (2) | 0.24128 (12) | 0.0166 (2) | |
| O3 | 0.84512 (9) | 0.9655 (2) | 0.24066 (10) | 0.0169 (2) | |
| O4 | 0.71429 (11) | 0.8243 (2) | 0.04689 (12) | 0.0174 (2) | |
| O5 | 0.53574 (10) | 0.5438 (2) | 0.59191 (10) | 0.0182 (2) | |
| N1 | 0.45216 (10) | 0.5969 (2) | 0.35282 (12) | 0.0115 (2) | |
| H1A | 0.4004 | 0.5615 | 0.2963 | 0.014* | |
| H1B | 0.5006 | 0.6972 | 0.3177 | 0.014* | |
| C1 | 0.48749 (16) | 0.7571 (3) | 0.55316 (16) | 0.0192 (3) | |
| H1C | 0.5433 | 0.8596 | 0.5180 | 0.023* | |
| H1D | 0.4557 | 0.8378 | 0.6238 | 0.023* | |
| C2 | 0.40096 (14) | 0.7119 (3) | 0.45982 (14) | 0.0151 (3) | |
| H2A | 0.3446 | 0.6099 | 0.4943 | 0.018* | |
| H2B | 0.3671 | 0.8603 | 0.4350 | 0.018* | |
| C3 | 0.50859 (13) | 0.3794 (3) | 0.39090 (15) | 0.0141 (3) | |
| H3A | 0.5476 | 0.3123 | 0.3210 | 0.017* | |
| H3B | 0.4553 | 0.2635 | 0.4191 | 0.017* | |
| C4 | 0.58711 (12) | 0.4327 (3) | 0.49177 (14) | 0.0138 (3) | |
| H4A | 0.6208 | 0.2861 | 0.5196 | 0.017* | |
| H4B | 0.6447 | 0.5350 | 0.4603 | 0.017* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Re1 | 0.00842 (2) | 0.01046 (2) | 0.00962 (2) | 0.00157 (1) | −0.00002 (7) | 0.00069 (7) |
| O1 | 0.0140 (5) | 0.0163 (5) | 0.0182 (5) | 0.0030 (4) | 0.0045 (4) | 0.0027 (4) |
| O2 | 0.0157 (5) | 0.0128 (5) | 0.0213 (5) | 0.0040 (4) | 0.0013 (4) | 0.0046 (4) |
| O3 | 0.0130 (5) | 0.0193 (6) | 0.0183 (5) | −0.0017 (4) | 0.0005 (4) | −0.0049 (4) |
| O4 | 0.0184 (6) | 0.0208 (6) | 0.0129 (5) | 0.0022 (4) | −0.0027 (4) | 0.0009 (4) |
| O5 | 0.0269 (6) | 0.0186 (6) | 0.0092 (5) | 0.0108 (5) | −0.0016 (4) | 0.0001 (4) |
| N1 | 0.0126 (5) | 0.0139 (6) | 0.0080 (5) | −0.0006 (5) | −0.0014 (4) | −0.0015 (5) |
| C1 | 0.0298 (9) | 0.0169 (7) | 0.0109 (7) | 0.0106 (6) | −0.0049 (6) | −0.0034 (6) |
| C2 | 0.0170 (7) | 0.0175 (7) | 0.0109 (7) | 0.0061 (6) | 0.0017 (5) | 0.0021 (6) |
| C3 | 0.0157 (7) | 0.0118 (7) | 0.0148 (6) | 0.0014 (5) | −0.0021 (5) | −0.0046 (6) |
| C4 | 0.0131 (6) | 0.0152 (7) | 0.0130 (6) | 0.0031 (5) | −0.0019 (5) | −0.0025 (5) |
| Re1—O1 | 1.7361 (11) | C1—C2 | 1.513 (2) |
| Re1—O2 | 1.7349 (13) | C1—H1C | 0.9900 |
| Re1—O3 | 1.7224 (11) | C1—H1D | 0.9900 |
| Re1—O4 | 1.7256 (13) | C2—H2A | 0.9900 |
| O5—C4 | 1.4279 (19) | C2—H2B | 0.9900 |
| O5—C1 | 1.430 (2) | C3—C4 | 1.513 (2) |
| N1—C3 | 1.494 (2) | C3—H3A | 0.9900 |
| N1—C2 | 1.496 (2) | C3—H3B | 0.9900 |
| N1—H1A | 0.9200 | C4—H4A | 0.9900 |
| N1—H1B | 0.9200 | C4—H4B | 0.9900 |
| O1—Re1—O2 | 108.44 (6) | N1—C2—C1 | 108.11 (14) |
| O1—Re1—O3 | 110.39 (6) | N1—C2—H2A | 110.1 |
| O1—Re1—O4 | 109.41 (6) | C1—C2—H2A | 110.1 |
| O2—Re1—O3 | 110.14 (6) | N1—C2—H2B | 110.1 |
| O2—Re1—O4 | 109.39 (6) | C1—C2—H2B | 110.1 |
| O3—Re1—O4 | 109.06 (6) | H2A—C2—H2B | 108.4 |
| C4—O5—C1 | 109.84 (12) | N1—C3—C4 | 109.94 (13) |
| C3—N1—C2 | 110.34 (12) | N1—C3—H3A | 109.7 |
| C3—N1—H1A | 109.6 | C4—C3—H3A | 109.7 |
| C2—N1—H1A | 109.6 | N1—C3—H3B | 109.7 |
| C3—N1—H1B | 109.6 | C4—C3—H3B | 109.7 |
| C2—N1—H1B | 109.6 | H3A—C3—H3B | 108.2 |
| H1A—N1—H1B | 108.1 | O5—C4—C3 | 111.83 (12) |
| O5—C1—C2 | 110.81 (15) | O5—C4—H4A | 109.3 |
| O5—C1—H1C | 109.5 | C3—C4—H4A | 109.3 |
| C2—C1—H1C | 109.5 | O5—C4—H4B | 109.3 |
| O5—C1—H1D | 109.5 | C3—C4—H4B | 109.3 |
| C2—C1—H1D | 109.5 | H4A—C4—H4B | 107.9 |
| H1C—C1—H1D | 108.1 | ||
| C4—O5—C1—C2 | 62.46 (19) | C2—N1—C3—C4 | −54.28 (17) |
| C3—N1—C2—C1 | 56.60 (17) | C1—O5—C4—C3 | −59.46 (19) |
| O5—C1—C2—N1 | −60.92 (18) | N1—C3—C4—O5 | 55.57 (17) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O2i | 0.92 | 1.99 | 2.8529 (17) | 155 |
| N1—H1B···O1 | 0.92 | 1.98 | 2.8855 (18) | 168 |
| Symmetry codes: (i) x−1/2, −y+1, z. |
| Re1—O1 | 1.7361 (11) | Re1—O3 | 1.7224 (11) |
| Re1—O2 | 1.7349 (13) | Re1—O4 | 1.7256 (13) |
| O1—Re1—O2 | 108.44 (6) | O2—Re1—O3 | 110.14 (6) |
| O1—Re1—O3 | 110.39 (6) | O2—Re1—O4 | 109.39 (6) |
| O1—Re1—O4 | 109.41 (6) | O3—Re1—O4 | 109.06 (6) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O2i | 0.92 | 1.99 | 2.8529 (17) | 155 |
| N1—H1B···O1 | 0.92 | 1.98 | 2.8855 (18) | 168 |
| Symmetry codes: (i) x−1/2, −y+1, z. |
Bruker (1998). SAINT-Plus. Version 6.01. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Grigoriev, M. S., German, K. E. & Maruk, A. Ya. (2007). Acta Cryst. E63, m2061–?.
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2004). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
The title compound, (I) (Fig. 1), contains slightly distorted tetrahedral ReO4− anions with Re—O distances from 1.7224 (11) to 1.7361 (11) Å (Table 1). Morpholinium cations have chair conformation.
The structure of (I) can be described as alternating cationic and anionic layers parallel to the (100) plane (Fig. 2). Morpholinium cations act as proton donors in two hydrogen bonds with O atoms of two ReO4− anions from different anionic layers (Table 2). The hydrogen bonds link cations and anions into chains in the [100] direction (Fig. 2).