


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808037124/tk2322sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808037124/tk2322Isup2.hkl |
CCDC reference: 712469
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.009 Å
- R factor = 0.066
- wR factor = 0.215
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C Value of measurement temperature given = 298.000 Value of melting point given = 0.000 SHFSU01_ALERT_2_C Test not performed. _refine_ls_shift/su_max and _refine_ls_shift/esd_max not present. Absolute value of the parameter shift to su ratio given 0.001 PLAT083_ALERT_2_C SHELXL Second Parameter in WGHT unusually Large. 16.00 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.48 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT234_ALERT_4_C Large Hirshfeld Difference N2 -- C12 .. 0.11 Ang. PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of the ionic liquid 1-(2-aminoethyl)-3-methylimidazolium hexafluorophosphate (5 mmol) and 2-hydroxybenzaldehyde (5 mmol) in ethanol was stirred for 4 h. After the completion of the reaction, the excess ethanol was removed by distillation. The colorless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution of (I) at room temperature.
The H atom bound to O1 was located from a difference Fourier map and refined as riding, with O—H = 0.82 Å, and with Uiso(H) = 1.5 Ueq(O). The remaining H atoms were located in a difference syntheses and refined with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2 - 1.5Ueq(C)].
Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![]() | Fig. 1. The molecular structure of the cation in (I) showing the atom numbering Scheme. Displacement ellipsoids are drawn at the 50% probability level. |
C13H16N3O+·PF6− | F(000) = 1536 |
Mr = 375.26 | Dx = 1.561 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2060 reflections |
a = 28.239 (15) Å | θ = 2.9–22.9° |
b = 7.134 (4) Å | µ = 0.24 mm−1 |
c = 18.017 (9) Å | T = 298 K |
β = 118.342 (6)° | Prism, yellow |
V = 3194 (3) Å3 | 0.32 × 0.25 × 0.15 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 2969 independent reflections |
Radiation source: fine-focus sealed tube | 1965 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ϕ and ω scans | θmax = 25.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→34 |
Tmin = 0.926, Tmax = 0.965 | k = −8→8 |
8091 measured reflections | l = −21→19 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.215 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.095P)2 + 15.5678P] where P = (Fo2 + 2Fc2)/3 |
2969 reflections | (Δ/σ)max < 0.001 |
221 parameters | Δρmax = 0.72 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C13H16N3O+·PF6− | V = 3194 (3) Å3 |
Mr = 375.26 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 28.239 (15) Å | µ = 0.24 mm−1 |
b = 7.134 (4) Å | T = 298 K |
c = 18.017 (9) Å | 0.32 × 0.25 × 0.15 mm |
β = 118.342 (6)° |
Bruker SMART CCD area-detector diffractometer | 2969 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1965 reflections with I > 2σ(I) |
Tmin = 0.926, Tmax = 0.965 | Rint = 0.043 |
8091 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.215 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.095P)2 + 15.5678P] where P = (Fo2 + 2Fc2)/3 |
2969 reflections | Δρmax = 0.72 e Å−3 |
221 parameters | Δρmin = −0.29 e Å−3 |
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 | ||
P1 | 0.7500 | 0.7500 | 0.0000 | 0.0501 (5) | |
P2 | 1.0000 | 0.6525 (3) | 0.2500 | 0.0583 (5) | |
F1 | 0.81350 (11) | 0.7434 (5) | 0.05733 (18) | 0.0696 (9) | |
F2 | 0.74441 (13) | 0.5737 (5) | 0.04985 (19) | 0.0742 (9) | |
F3 | 0.74598 (13) | 0.8887 (5) | 0.06617 (18) | 0.0737 (9) | |
F4 | 1.0089 (2) | 0.5007 (9) | 0.3170 (3) | 0.159 (2) | |
F5 | 0.93929 (17) | 0.6504 (10) | 0.2199 (4) | 0.162 (2) | |
F6 | 1.0081 (3) | 0.8057 (8) | 0.3156 (3) | 0.156 (2) | |
O1 | 0.80570 (15) | 0.2094 (7) | 0.2303 (3) | 0.0801 (12) | |
H1 | 0.8137 | 0.1973 | 0.1923 | 0.120* | |
N1 | 0.86812 (17) | 0.1728 (6) | 0.1638 (3) | 0.0551 (10) | |
N2 | 0.86519 (16) | 0.3299 (5) | −0.0349 (2) | 0.0513 (10) | |
N3 | 0.85173 (18) | 0.3101 (6) | −0.1622 (3) | 0.0591 (11) | |
C1 | 0.8504 (2) | 0.1958 (7) | 0.3054 (3) | 0.0566 (12) | |
C2 | 0.8461 (3) | 0.2063 (8) | 0.3792 (4) | 0.0671 (15) | |
H2 | 0.8126 | 0.2218 | 0.3762 | 0.081* | |
C3 | 0.8914 (3) | 0.1938 (8) | 0.4566 (4) | 0.0722 (16) | |
H3 | 0.8882 | 0.2028 | 0.5055 | 0.087* | |
C4 | 0.9408 (3) | 0.1686 (8) | 0.4625 (4) | 0.0719 (16) | |
H4 | 0.9710 | 0.1597 | 0.5152 | 0.086* | |
C5 | 0.9460 (2) | 0.1563 (7) | 0.3911 (3) | 0.0626 (13) | |
H5 | 0.9799 | 0.1381 | 0.3956 | 0.075* | |
C6 | 0.90111 (19) | 0.1708 (6) | 0.3114 (3) | 0.0491 (11) | |
C7 | 0.9077 (2) | 0.1593 (7) | 0.2363 (3) | 0.0536 (12) | |
H7 | 0.9419 | 0.1416 | 0.2420 | 0.064* | |
C8 | 0.8777 (2) | 0.1599 (7) | 0.0908 (3) | 0.0600 (13) | |
H8A | 0.8596 | 0.0508 | 0.0571 | 0.072* | |
H8B | 0.9160 | 0.1475 | 0.1095 | 0.072* | |
C9 | 0.8567 (2) | 0.3333 (8) | 0.0397 (3) | 0.0634 (14) | |
H9A | 0.8185 | 0.3450 | 0.0217 | 0.076* | |
H9B | 0.8748 | 0.4416 | 0.0741 | 0.076* | |
C10 | 0.9137 (2) | 0.3503 (8) | −0.0329 (3) | 0.0612 (13) | |
H10 | 0.9466 | 0.3686 | 0.0150 | 0.073* | |
C11 | 0.9053 (2) | 0.3392 (8) | −0.1120 (3) | 0.0627 (13) | |
H11 | 0.9312 | 0.3494 | −0.1297 | 0.075* | |
C12 | 0.8285 (2) | 0.3056 (7) | −0.1133 (3) | 0.0612 (13) | |
H12 | 0.7920 | 0.2881 | −0.1319 | 0.073* | |
C13 | 0.8247 (3) | 0.2925 (10) | −0.2541 (3) | 0.087 (2) | |
H13A | 0.7873 | 0.2649 | −0.2742 | 0.131* | |
H13B | 0.8410 | 0.1930 | −0.2699 | 0.131* | |
H13C | 0.8280 | 0.4080 | −0.2786 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0469 (10) | 0.0621 (11) | 0.0450 (9) | 0.0109 (8) | 0.0248 (8) | 0.0034 (8) |
P2 | 0.0526 (11) | 0.0736 (13) | 0.0541 (10) | 0.000 | 0.0296 (9) | 0.000 |
F1 | 0.0422 (16) | 0.088 (2) | 0.0708 (19) | 0.0081 (15) | 0.0202 (14) | −0.0014 (16) |
F2 | 0.084 (2) | 0.075 (2) | 0.0696 (19) | 0.0024 (17) | 0.0408 (17) | 0.0159 (16) |
F3 | 0.084 (2) | 0.082 (2) | 0.0611 (18) | 0.0150 (17) | 0.0393 (17) | −0.0107 (15) |
F4 | 0.181 (5) | 0.157 (5) | 0.135 (4) | −0.002 (4) | 0.073 (4) | 0.072 (4) |
F5 | 0.063 (3) | 0.243 (7) | 0.174 (5) | −0.004 (3) | 0.051 (3) | −0.033 (5) |
F6 | 0.209 (6) | 0.150 (5) | 0.108 (4) | −0.003 (4) | 0.076 (4) | −0.052 (3) |
O1 | 0.055 (2) | 0.116 (3) | 0.080 (3) | −0.006 (2) | 0.040 (2) | −0.018 (2) |
N1 | 0.058 (3) | 0.061 (2) | 0.057 (2) | 0.001 (2) | 0.035 (2) | −0.002 (2) |
N2 | 0.056 (2) | 0.051 (2) | 0.046 (2) | 0.0114 (18) | 0.0238 (19) | 0.0029 (17) |
N3 | 0.069 (3) | 0.056 (2) | 0.051 (2) | 0.004 (2) | 0.027 (2) | 0.0005 (19) |
C1 | 0.062 (3) | 0.053 (3) | 0.070 (3) | −0.009 (2) | 0.043 (3) | −0.004 (2) |
C2 | 0.078 (4) | 0.063 (3) | 0.089 (4) | −0.009 (3) | 0.062 (4) | −0.006 (3) |
C3 | 0.111 (5) | 0.056 (3) | 0.077 (4) | −0.003 (3) | 0.067 (4) | 0.005 (3) |
C4 | 0.092 (4) | 0.068 (4) | 0.060 (3) | 0.007 (3) | 0.040 (3) | 0.009 (3) |
C5 | 0.064 (3) | 0.063 (3) | 0.063 (3) | 0.011 (3) | 0.033 (3) | 0.010 (3) |
C6 | 0.056 (3) | 0.046 (2) | 0.053 (3) | 0.002 (2) | 0.031 (2) | 0.003 (2) |
C7 | 0.057 (3) | 0.050 (3) | 0.069 (3) | 0.005 (2) | 0.042 (3) | 0.005 (2) |
C8 | 0.072 (3) | 0.061 (3) | 0.062 (3) | 0.003 (3) | 0.044 (3) | −0.006 (2) |
C9 | 0.079 (4) | 0.065 (3) | 0.057 (3) | 0.016 (3) | 0.042 (3) | 0.003 (2) |
C10 | 0.049 (3) | 0.068 (3) | 0.063 (3) | 0.003 (2) | 0.024 (2) | 0.003 (3) |
C11 | 0.065 (3) | 0.067 (3) | 0.067 (3) | 0.006 (3) | 0.040 (3) | 0.008 (3) |
C12 | 0.056 (3) | 0.062 (3) | 0.066 (3) | −0.001 (2) | 0.029 (3) | −0.005 (3) |
C13 | 0.105 (5) | 0.101 (5) | 0.047 (3) | 0.002 (4) | 0.029 (3) | −0.005 (3) |
P1—F1i | 1.589 (3) | C1—C6 | 1.396 (7) |
P1—F1 | 1.589 (3) | C2—C3 | 1.377 (8) |
P1—F3 | 1.594 (3) | C2—H2 | 0.9300 |
P1—F3i | 1.594 (3) | C3—C4 | 1.359 (8) |
P1—F2i | 1.596 (3) | C3—H3 | 0.9300 |
P1—F2 | 1.596 (3) | C4—C5 | 1.366 (7) |
P2—F5ii | 1.533 (4) | C4—H4 | 0.9300 |
P2—F5 | 1.533 (4) | C5—C6 | 1.398 (7) |
P2—F6 | 1.544 (5) | C5—H5 | 0.9300 |
P2—F6ii | 1.544 (5) | C6—C7 | 1.454 (6) |
P2—F4ii | 1.550 (5) | C7—H7 | 0.9300 |
P2—F4 | 1.550 (5) | C8—C9 | 1.487 (7) |
O1—C1 | 1.346 (6) | C8—H8A | 0.9700 |
O1—H1 | 0.8200 | C8—H8B | 0.9700 |
N1—C7 | 1.256 (6) | C9—H9A | 0.9700 |
N1—C8 | 1.467 (6) | C9—H9B | 0.9700 |
N2—C12 | 1.308 (6) | C10—C11 | 1.333 (7) |
N2—C10 | 1.360 (6) | C10—H10 | 0.9300 |
N2—C9 | 1.474 (6) | C11—H11 | 0.9300 |
N3—C12 | 1.324 (6) | C12—H12 | 0.9300 |
N3—C11 | 1.360 (7) | C13—H13A | 0.9600 |
N3—C13 | 1.464 (6) | C13—H13B | 0.9600 |
C1—C2 | 1.392 (7) | C13—H13C | 0.9600 |
F1i—P1—F1 | 180.00 (12) | C1—C2—H2 | 119.9 |
F1i—P1—F3 | 90.50 (16) | C4—C3—C2 | 120.9 (5) |
F1—P1—F3 | 89.50 (16) | C4—C3—H3 | 119.6 |
F1i—P1—F3i | 89.50 (16) | C2—C3—H3 | 119.6 |
F1—P1—F3i | 90.50 (16) | C3—C4—C5 | 120.1 (6) |
F3—P1—F3i | 180.0 (2) | C3—C4—H4 | 120.0 |
F1i—P1—F2i | 89.62 (17) | C5—C4—H4 | 120.0 |
F1—P1—F2i | 90.38 (17) | C4—C5—C6 | 120.8 (5) |
F3—P1—F2i | 89.60 (17) | C4—C5—H5 | 119.6 |
F3i—P1—F2i | 90.40 (17) | C6—C5—H5 | 119.6 |
F1i—P1—F2 | 90.38 (17) | C1—C6—C5 | 119.1 (4) |
F1—P1—F2 | 89.62 (17) | C1—C6—C7 | 121.1 (5) |
F3—P1—F2 | 90.40 (17) | C5—C6—C7 | 119.8 (4) |
F3i—P1—F2 | 89.60 (17) | N1—C7—C6 | 121.3 (4) |
F2i—P1—F2 | 180.0 (2) | N1—C7—H7 | 119.4 |
F5ii—P2—F5 | 178.9 (5) | C6—C7—H7 | 119.4 |
F5ii—P2—F6 | 90.1 (4) | N1—C8—C9 | 108.2 (4) |
F5—P2—F6 | 90.7 (3) | N1—C8—H8A | 110.1 |
F5ii—P2—F6ii | 90.7 (3) | C9—C8—H8A | 110.1 |
F5—P2—F6ii | 90.1 (3) | N1—C8—H8B | 110.1 |
F6—P2—F6ii | 89.9 (5) | C9—C8—H8B | 110.1 |
F5ii—P2—F4ii | 90.6 (3) | H8A—C8—H8B | 108.4 |
F5—P2—F4ii | 88.6 (3) | N2—C9—C8 | 111.1 (4) |
F6—P2—F4ii | 179.0 (4) | N2—C9—H9A | 109.4 |
F6ii—P2—F4ii | 89.3 (3) | C8—C9—H9A | 109.4 |
F5ii—P2—F4 | 88.6 (3) | N2—C9—H9B | 109.4 |
F5—P2—F4 | 90.6 (3) | C8—C9—H9B | 109.4 |
F6—P2—F4 | 89.3 (3) | H9A—C9—H9B | 108.0 |
F6ii—P2—F4 | 179.0 (4) | C11—C10—N2 | 107.4 (5) |
F4ii—P2—F4 | 91.4 (5) | C11—C10—H10 | 126.3 |
C1—O1—H1 | 109.5 | N2—C10—H10 | 126.3 |
C7—N1—C8 | 118.3 (4) | C10—C11—N3 | 107.3 (5) |
C12—N2—C10 | 108.3 (4) | C10—C11—H11 | 126.4 |
C12—N2—C9 | 126.8 (5) | N3—C11—H11 | 126.4 |
C10—N2—C9 | 124.9 (4) | N2—C12—N3 | 109.1 (5) |
C12—N3—C11 | 107.9 (4) | N2—C12—H12 | 125.5 |
C12—N3—C13 | 126.4 (5) | N3—C12—H12 | 125.5 |
C11—N3—C13 | 125.7 (5) | N3—C13—H13A | 109.5 |
O1—C1—C2 | 119.5 (5) | N3—C13—H13B | 109.5 |
O1—C1—C6 | 121.6 (4) | H13A—C13—H13B | 109.5 |
C2—C1—C6 | 118.9 (5) | N3—C13—H13C | 109.5 |
C3—C2—C1 | 120.3 (5) | H13A—C13—H13C | 109.5 |
C3—C2—H2 | 119.9 | H13B—C13—H13C | 109.5 |
O1—C1—C2—C3 | −179.6 (5) | C7—N1—C8—C9 | −123.0 (5) |
C6—C1—C2—C3 | 0.6 (8) | C12—N2—C9—C8 | 107.3 (6) |
C1—C2—C3—C4 | −0.9 (8) | C10—N2—C9—C8 | −72.1 (7) |
C2—C3—C4—C5 | 0.4 (9) | N1—C8—C9—N2 | 179.9 (4) |
C3—C4—C5—C6 | 0.5 (9) | C12—N2—C10—C11 | 0.5 (6) |
O1—C1—C6—C5 | −179.6 (5) | C9—N2—C10—C11 | 180.0 (5) |
C2—C1—C6—C5 | 0.3 (7) | N2—C10—C11—N3 | −0.6 (6) |
O1—C1—C6—C7 | 0.3 (7) | C12—N3—C11—C10 | 0.5 (6) |
C2—C1—C6—C7 | −179.9 (5) | C13—N3—C11—C10 | 178.9 (5) |
C4—C5—C6—C1 | −0.8 (8) | C10—N2—C12—N3 | −0.1 (6) |
C4—C5—C6—C7 | 179.3 (5) | C9—N2—C12—N3 | −179.6 (4) |
C8—N1—C7—C6 | −180.0 (4) | C11—N3—C12—N2 | −0.2 (6) |
C1—C6—C7—N1 | 0.5 (7) | C13—N3—C12—N2 | −178.6 (5) |
C5—C6—C7—N1 | −179.7 (5) |
Symmetry codes: (i) −x+3/2, −y+3/2, −z; (ii) −x+2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C13H16N3O+·PF6− |
Mr | 375.26 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 28.239 (15), 7.134 (4), 18.017 (9) |
β (°) | 118.342 (6) |
V (Å3) | 3194 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.32 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.926, 0.965 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8091, 2969, 1965 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.215, 1.01 |
No. of reflections | 2969 |
No. of parameters | 221 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.095P)2 + 15.5678P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.72, −0.29 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
The use of functionalized ionic liquids continues to receive attention in chemical synthesis and engineering, including as catalysts in organic synthesis (Cai et al., 2006; Peng & Song, 2006). Schiff base compounds are one of most prevalent mixed-donor ligands in the field of coordination chemistry (Pradeep, 2005; Butcher et al., 2005). Herein, we report the crystal structure of the title salt, (I).
Compound (I) is a Schiff base formed from the reaciton of 2-hydroxybenaldehyde and ionic liquid 1-(2-aminoethyl)-3-methylimidazolium hexafluorophosphate. The molecular structure of the cation is shown in Fig. 1. The aromatic and imidazole rings form a dihedral angle of 15.2 (2)°. In the cation, an intramolecular O1—H1···N1 hydrogen bond leads to a six-membered ring S(6) motif, Table 1.