Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039608/ng2306sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039608/ng2306Isup2.hkl |
CCDC reference: 660116
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (Wave) = 0.000 Å
- R factor = 0.010
- wR factor = 0.020
- Data-to-parameter ratio = 34.3
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.239 0.309 Tmin and Tmax expected: 0.123 0.215 RR = 1.353 Please check that your absorption correction is appropriate.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.697 Tmax scaled 0.215 Tmin scaled 0.167 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 35.00 From the CIF: _reflns_number_total 3460 Count of symmetry unique reflns 1811 Completeness (_total/calc) 191.05% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1649 Fraction of Friedel pairs measured 0.911 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
See Grigoriev et al. (2007) for the structure of guanidinium tetraoxidorhenate.
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.
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).
See Grigoriev et al. (2007) for the structure of guanidinium tetraoxidorhenate.
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).
(C4H10NO)[ReO4] | F(000) = 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 = 3.3–35.0° |
b = 5.7480 (2) Å | µ = 15.37 mm−1 |
c = 11.0420 (3) Å | T = 100 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) |
Graphite monochromator | Rint = 0.021 |
ω and φ scans | θmax = 35.0°, θmin = 3.3° |
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 | Absolute structure parameter: 0.004 (4) |
(C4H10NO)[ReO4] | V = 789.57 (4) Å3 |
Mr = 338.33 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 12.4401 (3) Å | µ = 15.37 mm−1 |
b = 5.7480 (2) Å | T = 100 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 | Absolute structure 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 > 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 | 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 code: (i) x−1/2, −y+1, z. |
Experimental details
Crystal data | |
Chemical formula | (C4H10NO)[ReO4] |
Mr | 338.33 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 100 |
a, b, c (Å) | 12.4401 (3), 5.7480 (2), 11.0420 (3) |
V (Å3) | 789.57 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 15.37 |
Crystal size (mm) | 0.16 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker Kappa APEX II area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.239, 0.309 |
No. of measured, independent and observed [I > 2α(I)] reflections | 21183, 3460, 3315 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.807 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.010, 0.020, 0.94 |
No. of reflections | 3460 |
No. of parameters | 101 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −0.60 |
Absolute structure | Flack (1983), with 1650 Friedel pairs |
Absolute structure parameter | 0.004 (4) |
Computer programs: APEX2 (Bruker, 2006), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
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) | 154.8 |
N1—H1B···O1 | 0.92 | 1.98 | 2.8855 (18) | 167.8 |
Symmetry code: (i) x−1/2, −y+1, z. |
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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).