Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201499X/bt6184sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680201499X/bt6184Isup2.hkl |
CCDC reference: 197456
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.025
- wR factor = 0.060
- Data-to-parameter ratio = 13.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.716 0.846 Tmin' and Tmax expected: 0.947 0.981 RR' = 0.876 Please check that your absorption correction is appropriate. STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack -0.200 From the CIF: _refine_ls_abs_structure_Flack_su 1.100 Alert C Flack test results are meaningless. General Notes
ABSTM_02 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 1.159 Tmax scaled 0.981 Tmin scaled 0.830 REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 1367 Count of symmetry unique reflns 849 Completeness (_total/calc) 161.01% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 518 Fraction of Friedel pairs measured 0.610 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Preparations were carried out in a dry room (<1% relative humidity). LiNO3 (Aldrich) was dried at 393 K under high vacuum for 24 h. Anhydrous monoglyme (1,2-dimethoxyethane; 99.5%, Aldrich) was used as received. The title compound was formed by the addition of excess monoglyme to the salt. Single crystals grew rapidly at room temperature. A phase diagram of the monoglyme–LiNO3 system could not be prepared as heating the mixtures does not result in homogeneous liquids. Rather, the title compound melts and the salt, LiNO3, precipitates out of the mixture.
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Bruker, 1998); software used to prepare material for publication: SHELXTL/PC (Bruker, 1998) and PLATON (Spek, 2001).
[Li(NO3)(C4H10O2)] | Dx = 1.359 Mg m−3 |
Mr = 159.07 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, P3121 | Cell parameters from 2682 reflections |
a = 7.4925 (5) Å | θ = 3.1–23.8° |
c = 23.989 (3) Å | µ = 0.12 mm−1 |
V = 1166.3 (2) Å3 | T = 173 K |
Z = 6 | Block, colourless |
F(000) = 504 | 0.44 × 0.16 × 0.16 mm |
Siemens CCD area-detector diffractometer | 1367 independent reflections |
Radiation source: fine-focus sealed tube | 1255 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Blessing, 1995; Sheldrick, 2000) | h = −8→8 |
Tmin = 0.716, Tmax = 0.846 | k = −8→8 |
5711 measured reflections | l = −28→25 |
Refinement on F2 | Hydrogen site location: placed geometrically |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.025 | w = 1/[σ2(Fo2) + (0.0312P)2 + 0.0933P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.060 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.10 e Å−3 |
1367 reflections | Δρmin = −0.11 e Å−3 |
104 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0059 (15) |
Primary atom site location: direct methods | Absolute structure: Flack (1983), 0000 Friedel pairs |
Secondary atom site location: difference Fourier synthesis | Absolute structure parameter: −0.2 (11) |
[Li(NO3)(C4H10O2)] | Z = 6 |
Mr = 159.07 | Mo Kα radiation |
Trigonal, P3121 | µ = 0.12 mm−1 |
a = 7.4925 (5) Å | T = 173 K |
c = 23.989 (3) Å | 0.44 × 0.16 × 0.16 mm |
V = 1166.3 (2) Å3 |
Siemens CCD area-detector diffractometer | 1367 independent reflections |
Absorption correction: multi-scan (SADABS; Blessing, 1995; Sheldrick, 2000) | 1255 reflections with I > 2σ(I) |
Tmin = 0.716, Tmax = 0.846 | Rint = 0.025 |
5711 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.060 | Δρmax = 0.10 e Å−3 |
S = 1.06 | Δρmin = −0.11 e Å−3 |
1367 reflections | Absolute structure: Flack (1983), 0000 Friedel pairs |
104 parameters | Absolute structure parameter: −0.2 (11) |
0 restraints |
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 | ||
Li1 | 0.0000 | −0.1863 (4) | 0.1667 | 0.0319 (7) | |
Li2 | 0.2464 (5) | 0.2464 (5) | 0.0000 | 0.0370 (8) | |
O1 | −0.19362 (13) | −0.48621 (14) | 0.14834 (4) | 0.0294 (2) | |
C1 | −0.4097 (2) | −0.5737 (2) | 0.15760 (7) | 0.0369 (4) | |
H1A | −0.4372 | −0.5854 | 0.1978 | 0.055* | |
H1B | −0.4837 | −0.7108 | 0.1405 | 0.055* | |
H1C | −0.4566 | −0.4850 | 0.1408 | 0.055* | |
C2 | −0.1143 (2) | −0.6077 (2) | 0.17184 (7) | 0.0336 (4) | |
H2A | −0.1791 | −0.7451 | 0.1540 | 0.040* | |
H2B | −0.1430 | −0.6265 | 0.2123 | 0.040* | |
O2 | 0.53970 (15) | 0.35352 (14) | 0.02001 (4) | 0.0353 (3) | |
C3 | 0.6403 (3) | 0.2348 (3) | 0.02289 (7) | 0.0453 (4) | |
H3A | 0.7632 | 0.3061 | 0.0464 | 0.068* | |
H3B | 0.6808 | 0.2175 | −0.0147 | 0.068* | |
H3C | 0.5460 | 0.0993 | 0.0389 | 0.068* | |
C4 | 0.6692 (2) | 0.5533 (2) | −0.00218 (7) | 0.0374 (4) | |
H4A | 0.7027 | 0.5438 | −0.0416 | 0.045* | |
H4B | 0.7995 | 0.6250 | 0.0192 | 0.045* | |
N1 | 0.00426 (18) | 0.02720 (17) | 0.08617 (5) | 0.0275 (3) | |
O3 | 0.14202 (16) | −0.02032 (16) | 0.08818 (4) | 0.0370 (3) | |
O4 | −0.14688 (15) | −0.05930 (15) | 0.11836 (4) | 0.0347 (3) | |
O5 | 0.01781 (18) | 0.16051 (17) | 0.05232 (4) | 0.0420 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Li1 | 0.0334 (19) | 0.0281 (13) | 0.0361 (19) | 0.0167 (9) | 0.0013 (15) | 0.0007 (8) |
Li2 | 0.0314 (13) | 0.0314 (13) | 0.046 (2) | 0.0139 (16) | 0.0026 (8) | −0.0026 (8) |
O1 | 0.0260 (5) | 0.0254 (5) | 0.0373 (6) | 0.0132 (4) | 0.0005 (4) | 0.0010 (4) |
C1 | 0.0284 (8) | 0.0364 (8) | 0.0439 (9) | 0.0148 (7) | 0.0011 (7) | −0.0013 (7) |
C2 | 0.0338 (9) | 0.0240 (8) | 0.0442 (9) | 0.0153 (7) | 0.0001 (7) | 0.0016 (6) |
O2 | 0.0325 (6) | 0.0327 (6) | 0.0436 (6) | 0.0183 (5) | −0.0010 (5) | 0.0031 (5) |
C3 | 0.0518 (10) | 0.0477 (10) | 0.0510 (10) | 0.0358 (9) | −0.0008 (8) | 0.0009 (8) |
C4 | 0.0290 (8) | 0.0338 (8) | 0.0483 (10) | 0.0148 (7) | −0.0006 (7) | 0.0002 (7) |
N1 | 0.0280 (6) | 0.0265 (6) | 0.0288 (6) | 0.0143 (5) | −0.0009 (5) | −0.0013 (5) |
O3 | 0.0338 (6) | 0.0436 (6) | 0.0412 (6) | 0.0250 (5) | 0.0008 (4) | 0.0010 (5) |
O4 | 0.0295 (6) | 0.0364 (6) | 0.0363 (6) | 0.0151 (5) | 0.0080 (5) | 0.0064 (4) |
O5 | 0.0503 (7) | 0.0450 (7) | 0.0407 (7) | 0.0313 (6) | 0.0100 (5) | 0.0170 (5) |
Li1—O1i | 2.021 (2) | Li2—N1ii | 2.699 (2) |
Li1—O1 | 2.021 (2) | Li2—N1 | 2.699 (2) |
Li1—O4i | 2.123 (2) | O1—C1 | 1.4281 (16) |
Li1—O4 | 2.123 (2) | O1—C2 | 1.4285 (16) |
Li1—O3i | 2.2138 (14) | C2—C2i | 1.504 (3) |
Li1—O3 | 2.2138 (14) | O2—C4 | 1.4187 (18) |
Li1—N1i | 2.498 (2) | O2—C3 | 1.4260 (18) |
Li1—N1 | 2.498 (2) | C4—C4ii | 1.509 (3) |
Li2—O5ii | 1.955 (2) | N1—O3 | 1.2498 (15) |
Li2—O5 | 1.955 (2) | N1—O4 | 1.2510 (15) |
Li2—O2 | 1.985 (3) | N1—O5 | 1.2514 (14) |
Li2—O2ii | 1.985 (3) | ||
O1i—Li1—O1 | 82.37 (12) | O5—Li2—O2ii | 108.81 (5) |
O1i—Li1—O4i | 97.75 (4) | O2—Li2—O2ii | 81.83 (15) |
O1—Li1—O4i | 158.47 (4) | O5ii—Li2—N1ii | 25.31 (5) |
O1i—Li1—O4 | 158.47 (4) | O5—Li2—N1ii | 97.58 (13) |
O1—Li1—O4 | 97.75 (4) | O2—Li2—N1ii | 129.47 (4) |
O4i—Li1—O4 | 89.93 (13) | O2ii—Li2—N1ii | 109.41 (4) |
O1i—Li1—O3i | 108.41 (6) | O5ii—Li2—N1 | 97.58 (13) |
O1—Li1—O3i | 99.69 (6) | O5—Li2—N1 | 25.31 (5) |
O4i—Li1—O3i | 59.68 (6) | O2—Li2—N1 | 109.41 (4) |
O4—Li1—O3i | 92.85 (10) | O2ii—Li2—N1 | 129.47 (4) |
O1i—Li1—O3 | 99.69 (6) | N1ii—Li2—N1 | 100.34 (12) |
O1—Li1—O3 | 108.41 (6) | C1—O1—C2 | 112.55 (10) |
O4i—Li1—O3 | 92.85 (10) | C1—O1—Li1 | 119.69 (9) |
O4—Li1—O3 | 59.68 (6) | C2—O1—Li1 | 109.05 (9) |
O3i—Li1—O3 | 142.48 (16) | O1—C2—C2i | 106.87 (9) |
O1i—Li1—N1i | 108.42 (4) | C4—O2—C3 | 112.33 (11) |
O1—Li1—N1i | 129.68 (4) | C4—O2—Li2 | 111.77 (10) |
O4i—Li1—N1i | 30.04 (4) | C3—O2—Li2 | 125.66 (11) |
O4—Li1—N1i | 88.18 (11) | O2—C4—C4ii | 107.11 (9) |
O3i—Li1—N1i | 30.00 (5) | O3—N1—O4 | 119.42 (11) |
O3—Li1—N1i | 117.27 (12) | O3—N1—O5 | 120.24 (12) |
O1i—Li1—N1 | 129.68 (4) | O4—N1—O5 | 120.35 (11) |
O1—Li1—N1 | 108.42 (4) | O3—N1—Li1 | 62.32 (8) |
O4i—Li1—N1 | 88.18 (11) | O4—N1—Li1 | 58.17 (7) |
O4—Li1—N1 | 30.04 (4) | O5—N1—Li1 | 169.39 (10) |
O3i—Li1—N1 | 117.27 (12) | O3—N1—Li2 | 78.66 (7) |
O3—Li1—N1 | 30.00 (5) | O4—N1—Li2 | 161.29 (9) |
N1i—Li1—N1 | 101.29 (12) | O5—N1—Li2 | 41.89 (6) |
O5ii—Li2—O5 | 105.86 (17) | Li1—N1—Li2 | 140.48 (6) |
O5ii—Li2—O2 | 108.81 (5) | N1—O3—Li1 | 87.69 (10) |
O5—Li2—O2 | 126.05 (5) | N1—O4—Li1 | 91.79 (7) |
O5ii—Li2—O2ii | 126.05 (5) | N1—O5—Li2 | 112.80 (9) |
Symmetry codes: (i) −x, −x+y, −z+1/3; (ii) y, x, −z. |
Experimental details
Crystal data | |
Chemical formula | [Li(NO3)(C4H10O2)] |
Mr | 159.07 |
Crystal system, space group | Trigonal, P3121 |
Temperature (K) | 173 |
a, c (Å) | 7.4925 (5), 23.989 (3) |
V (Å3) | 1166.3 (2) |
Z | 6 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.44 × 0.16 × 0.16 |
Data collection | |
Diffractometer | Siemens CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Blessing, 1995; Sheldrick, 2000) |
Tmin, Tmax | 0.716, 0.846 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5711, 1367, 1255 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.060, 1.06 |
No. of reflections | 1367 |
No. of parameters | 104 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.10, −0.11 |
Absolute structure | Flack (1983), 0000 Friedel pairs |
Absolute structure parameter | −0.2 (11) |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Bruker, 1998) and PLATON (Spek, 2001).
Li1—O1 | 2.021 (2) | Li2—O5 | 1.955 (2) |
Li1—O4 | 2.123 (2) | Li2—O2 | 1.985 (3) |
Li1—O3 | 2.2138 (14) |
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Structural characterization of the title compound, (I), was performed as part of a comprehensive study of lithium salt phase behavior with glyme ligands (Henderson, 2002). LiNO3 tends to be highly associated into contact ion pair or aggregate solvate structures with ether solvents. During the course of preparing a phase diagram of the monoglyme–LiNO3 system, it was found that addition of excess monoglyme to the salt resulted in the rapid formation of long needle-like single crystals of (I). These crystals were structurally characterized to determine the stoichiometry of the crystalline phase formed.