Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027364/ob6577sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027364/ob6577Isup2.hkl |
CCDC reference: 287679
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.048
- wR factor = 0.123
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.767 0.986 Tmin(prime) and Tmax expected: 0.962 0.986 RR(prime) = 0.797 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.80 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion
Crystals of (I) were grown by slow evaporation of a satured solution of 18-crown-6 in liquid ammonia at 195 K.
All H atoms were located from difference maps and refined freely. The C—H and N—H distances are 0.93 (2)–1.01 (2) Å and 0.85 (3)–0.90 (3) Å, respectively.
Data collection: SMART32 (Bruker, 1997); cell refinement: SAINT32 (Bruker, 2003); data reduction: SAINT32; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: ATOMS (Dowty, 2002); software used to prepare material for publication: SHELXTL.
C12H24O6·2H3N | F(000) = 328 |
Mr = 298.38 | Dx = 1.203 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4789 (14) Å | Cell parameters from 1983 reflections |
b = 7.6632 (14) Å | θ = 5.5–59.7° |
c = 14.374 (3) Å | µ = 0.10 mm−1 |
β = 91.754 (4)° | T = 100 K |
V = 823.4 (3) Å3 | Needle, colorless |
Z = 2 | 0.4 × 0.2 × 0.15 mm |
Bruker SMART APEX diffractometer | 1983 independent reflections |
Radiation source: fine-focus sealed tube | 1400 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ω scans | θmax = 28.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −9→9 |
Tmin = 0.767, Tmax = 0.986 | k = −10→10 |
11143 measured reflections | l = −18→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0643P)2 + 0.1375P] where P = (Fo2 + 2Fc2)/3 |
1983 reflections | (Δ/σ)max < 0.001 |
151 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C12H24O6·2H3N | V = 823.4 (3) Å3 |
Mr = 298.38 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.4789 (14) Å | µ = 0.10 mm−1 |
b = 7.6632 (14) Å | T = 100 K |
c = 14.374 (3) Å | 0.4 × 0.2 × 0.15 mm |
β = 91.754 (4)° |
Bruker SMART APEX diffractometer | 1983 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 1400 reflections with I > 2σ(I) |
Tmin = 0.767, Tmax = 0.986 | Rint = 0.056 |
11143 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.123 | All H-atom parameters refined |
S = 1.05 | Δρmax = 0.31 e Å−3 |
1983 reflections | Δρmin = −0.17 e Å−3 |
151 parameters |
Experimental. Data collection is performed with three batch runs at ϕ = 0.00 ° (603 frames), at ϕ = 120.00 ° (603 frames) and at ϕ = 240.00 (603 frames). Frame width = 0.30 \& in ω. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. |
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 | ||
N1 | 0.1463 (2) | 0.1279 (2) | 0.58096 (11) | 0.0252 (3) | |
O1 | −0.01313 (14) | 0.30332 (14) | 0.39576 (7) | 0.0203 (3) | |
O2 | 0.23196 (13) | 0.03940 (14) | 0.34328 (7) | 0.0192 (3) | |
O3 | 0.30709 (14) | −0.22309 (15) | 0.48313 (8) | 0.0218 (3) | |
C1 | −0.1842 (2) | 0.3831 (2) | 0.39192 (13) | 0.0251 (4) | |
C2 | 0.0663 (2) | 0.2966 (2) | 0.30783 (11) | 0.0210 (4) | |
C3 | 0.2485 (2) | 0.2170 (2) | 0.31875 (12) | 0.0208 (4) | |
C4 | 0.4015 (2) | −0.0399 (2) | 0.36075 (12) | 0.0218 (4) | |
C5 | 0.3739 (2) | −0.2234 (2) | 0.39212 (11) | 0.0222 (4) | |
C6 | 0.2540 (2) | −0.3912 (2) | 0.51192 (13) | 0.0243 (4) | |
H11 | 0.192 (3) | 0.034 (4) | 0.5601 (17) | 0.051 (7)* | |
H22 | 0.042 (3) | 0.091 (3) | 0.6038 (16) | 0.050 (7)* | |
H33 | 0.109 (3) | 0.180 (3) | 0.5289 (18) | 0.047 (7)* | |
H1A | −0.176 (2) | 0.501 (3) | 0.3660 (13) | 0.027 (5)* | |
H1B | −0.260 (2) | 0.315 (2) | 0.3502 (13) | 0.024 (5)* | |
H2A | 0.076 (2) | 0.413 (2) | 0.2819 (13) | 0.022 (4)* | |
H2B | −0.010 (3) | 0.231 (3) | 0.2632 (13) | 0.027 (5)* | |
H3A | 0.318 (2) | 0.278 (2) | 0.3675 (13) | 0.022 (4)* | |
H3B | 0.303 (2) | 0.227 (2) | 0.2615 (14) | 0.026 (5)* | |
H4A | 0.463 (2) | 0.029 (2) | 0.4077 (12) | 0.018 (4)* | |
H4B | 0.465 (2) | −0.038 (2) | 0.3027 (13) | 0.021 (4)* | |
H5A | 0.292 (2) | −0.282 (2) | 0.3493 (12) | 0.018 (4)* | |
H5B | 0.490 (2) | −0.288 (2) | 0.3926 (13) | 0.026 (5)* | |
H6A | 0.160 (3) | −0.438 (2) | 0.4673 (13) | 0.028 (5)* | |
H6B | 0.354 (2) | −0.467 (2) | 0.5127 (12) | 0.022 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0203 (7) | 0.0309 (9) | 0.0244 (8) | 0.0000 (7) | 0.0002 (6) | −0.0011 (7) |
O1 | 0.0155 (5) | 0.0248 (6) | 0.0208 (6) | 0.0039 (4) | 0.0030 (4) | 0.0028 (4) |
O2 | 0.0122 (5) | 0.0200 (6) | 0.0254 (6) | 0.0006 (4) | 0.0028 (4) | 0.0015 (4) |
O3 | 0.0198 (6) | 0.0240 (6) | 0.0219 (6) | −0.0021 (5) | 0.0034 (4) | 0.0006 (5) |
C1 | 0.0175 (8) | 0.0273 (9) | 0.0305 (9) | 0.0056 (7) | 0.0020 (7) | 0.0096 (8) |
C2 | 0.0249 (8) | 0.0198 (8) | 0.0186 (8) | 0.0002 (7) | 0.0037 (6) | 0.0029 (6) |
C3 | 0.0189 (8) | 0.0223 (9) | 0.0214 (8) | −0.0022 (7) | 0.0064 (6) | −0.0001 (7) |
C4 | 0.0136 (7) | 0.0287 (9) | 0.0232 (9) | 0.0016 (7) | 0.0034 (6) | 0.0005 (7) |
C5 | 0.0192 (8) | 0.0253 (9) | 0.0221 (8) | 0.0048 (7) | 0.0019 (6) | −0.0003 (6) |
C6 | 0.0174 (7) | 0.0213 (9) | 0.0346 (10) | 0.0051 (7) | 0.0069 (7) | 0.0042 (7) |
N1—H11 | 0.85 (3) | C2—H2A | 0.972 (19) |
N1—H22 | 0.90 (3) | C2—H2B | 0.98 (2) |
N1—H33 | 0.89 (3) | C3—H3A | 0.982 (18) |
O1—C2 | 1.4137 (19) | C3—H3B | 0.93 (2) |
O1—C1 | 1.4178 (19) | C4—C5 | 1.493 (2) |
O2—C3 | 1.412 (2) | C4—H4A | 0.963 (18) |
O2—C4 | 1.4212 (18) | C4—H4B | 0.972 (18) |
O3—C6 | 1.414 (2) | C5—H5A | 0.967 (18) |
O3—C5 | 1.4146 (19) | C5—H5B | 1.001 (19) |
C1—C6i | 1.494 (2) | C6—C1i | 1.494 (2) |
C1—H1A | 0.98 (2) | C6—H6A | 1.005 (19) |
C1—H1B | 0.964 (19) | C6—H6B | 0.946 (19) |
C2—C3 | 1.497 (2) | ||
H11—N1—H22 | 103 (2) | O2—C3—H3B | 110.0 (11) |
H11—N1—H33 | 102 (2) | C2—C3—H3B | 107.1 (11) |
H22—N1—H33 | 101 (2) | H3A—C3—H3B | 110.9 (15) |
C2—O1—C1 | 112.59 (12) | O2—C4—C5 | 108.99 (13) |
C3—O2—C4 | 111.80 (12) | O2—C4—H4A | 107.3 (10) |
C6—O3—C5 | 112.29 (13) | C5—C4—H4A | 111.8 (11) |
O1—C1—C6i | 108.81 (14) | O2—C4—H4B | 107.3 (10) |
O1—C1—H1A | 110.4 (10) | C5—C4—H4B | 110.6 (10) |
C6i—C1—H1A | 109.9 (11) | H4A—C4—H4B | 110.7 (15) |
O1—C1—H1B | 107.6 (11) | O3—C5—C4 | 109.47 (13) |
C6i—C1—H1B | 112.5 (11) | O3—C5—H5A | 110.8 (10) |
H1A—C1—H1B | 107.7 (15) | C4—C5—H5A | 109.7 (10) |
O1—C2—C3 | 109.09 (13) | O3—C5—H5B | 109.1 (11) |
O1—C2—H2A | 110.3 (11) | C4—C5—H5B | 109.9 (10) |
C3—C2—H2A | 109.7 (11) | H5A—C5—H5B | 107.8 (14) |
O1—C2—H2B | 110.7 (11) | O3—C6—C1i | 110.03 (14) |
C3—C2—H2B | 111.6 (11) | O3—C6—H6A | 109.5 (11) |
H2A—C2—H2B | 105.5 (16) | C1i—C6—H6A | 110.3 (11) |
O2—C3—C2 | 109.39 (13) | O3—C6—H6B | 109.5 (11) |
O2—C3—H3A | 109.4 (11) | C1i—C6—H6B | 108.2 (11) |
C2—C3—H3A | 110.1 (10) | H6A—C6—H6B | 109.3 (15) |
Symmetry code: (i) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H33···O1 | 0.89 (3) | 2.30 (3) | 3.181 (2) | 175 (2) |
N1—H22···O2i | 0.90 (3) | 2.42 (3) | 3.320 (2) | 174 (2) |
N1—H11···O3 | 0.85 (3) | 2.43 (3) | 3.281 (2) | 173 (2) |
Symmetry code: (i) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C12H24O6·2H3N |
Mr | 298.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 7.4789 (14), 7.6632 (14), 14.374 (3) |
β (°) | 91.754 (4) |
V (Å3) | 823.4 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.4 × 0.2 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.767, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11143, 1983, 1400 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.660 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.123, 1.05 |
No. of reflections | 1983 |
No. of parameters | 151 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.31, −0.17 |
Computer programs: SMART32 (Bruker, 1997), SAINT32 (Bruker, 2003), SAINT32, SHELXTL (Sheldrick, 2000), SHELXTL, ATOMS (Dowty, 2002).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H33···O1 | 0.89 (3) | 2.30 (3) | 3.181 (2) | 175 (2) |
N1—H22···O2i | 0.90 (3) | 2.42 (3) | 3.320 (2) | 174 (2) |
N1—H11···O3 | 0.85 (3) | 2.43 (3) | 3.281 (2) | 173 (2) |
Symmetry code: (i) −x, −y, −z+1. |
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The group of cyclic polyethers, the so called crown ethers, certainly is one of the most useful substance classes in organic, metallorganic and inorganic chemistry. Crown ethers, which are tools to increase the solubility of inorganic salts in organic solvents (Yakshin, 2002), are able to coordinate to charged as well as neutral molecules (Elbasyouny et al., 1983; Huang et al., 1993; Doxsee et al., 2000) and have been used to isolate such unusual compounds as alkalides and electrides (Dye, 1984). The fact that almost every week new crown ether compounds are published confirm this impression. We report here on the title compound, (I), the 1:2 adduct of 18-crown-6 and ammonia, which forms a queue with other solvent–crown ether adducts starting with the water complexes of crown ethers (Newkome et al., 1981; Mootz et al., 1994) over acetonitrile compounds (Mosier-Boss & Popov, 1985; Mosier-Boss, 2005) to adducts containing formamide or nitromethane (Voegtle et al., 1980; de Boer et al., 1982).
Compound (I) has inversion symmetry (Fig. 1). The disc-like building blocks are stacked along the c axis with a tilt angle of 52.4 (s.u.?)° between the plane normal (line between the two N atoms) and the c axis (Fig. 2). The N—H···O hydrogen bonds (Table 1) connect the NH3 molecules with the crown ether. The H···O distances [2.30 (3)–2.43 (3) Å] fit to values recently reported for the {[Li(NH3)4]2[18-crown-6]2+ cation (Wiesler and Korber, 2005).