1-{2-[(2-hydroxybenzylidene)-amino]-ethyl}-3-methyl-3H-imidazolium hexafluorophosphate

Bin Li; Yi-Qun Li; Yue-Peng Cai; Mei-Yun Zhou

doi:10.1107/S1600536808037124

. 2008 Nov 13;64(Pt 12):o2365. doi: 10.1107/S1600536808037124

1-{2-[(2-hydroxybenzylidene)-amino]-ethyl}-3-methyl-3H-imidazolium hexafluorophosphate

Bin Li ^a, Yi-Qun Li ^a,^*, Yue-Peng Cai ^b, Mei-Yun Zhou ^a

PMCID: PMC2959942 PMID: 21581337

Abstract

The title Schiff base compound, C₁₃H₁₆N₃O⁺·PF₆ ⁻, was derived from the condensation of 2-hydroxybenaldehyde with the ionic liquid 1-(2-aminoethyl)-3-methylimidazolium hexafluorophosphate in an ethanol solution. The asymmetric unit comprises one cation and two PF₆ ⁻ anions. The dihedral angle between the aromatic and imidazole rings is 15.2 (2)°. An intramolecular O—H⋯N hydrogen bond is found which generates an S(6) ring motif.

Related literature

For the synthesis of Schiff bases, see: Pradeep (2005 ▶); Butcher et al. (2005 ▶). For background on ionic liquids and their applications, see: Cai et al. (2006 ▶); Peng & Song (2006 ▶).

Experimental

Crystal data

C₁₃H₁₆N₃O⁺·PF₆ ⁻
M _r = 375.26
Monoclinic,
a = 28.239 (15) Å
b = 7.134 (4) Å
c = 18.017 (9) Å
β = 118.342 (6)°
V = 3194 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 (2) K
0.32 × 0.25 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.926, T _max = 0.965
8091 measured reflections
2969 independent reflections
1965 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.215
S = 1.01
2969 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037124/tk2322sup1.cif

e-64-o2365-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037124/tk2322Isup2.hkl

e-64-o2365-Isup2.hkl^{(145.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.572 (5)	147

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Acknowledgments

We are grateful to the National Natural Science Foundation of China (No. 20672046) and the Guangdong Natural Science Foundation (No. 04010458) for financial support.

supplementary crystallographic information

Comment

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.

Experimental

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.

Figures

Fig. 1. — The molecular structure of the cation in (I) showing the atom numbering Scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C₁₃H₁₆N₃O⁺·PF₆^–	F₀₀₀ = 1536
M_r = 375.26	D_x = 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 = 2.9–22.9º
b = 7.134 (4) Å	µ = 0.24 mm⁻¹
c = 18.017 (9) Å	T = 298 (2) K
β = 118.342 (6)º	Prism, yellow
V = 3194 (3) Å³	0.32 × 0.25 × 0.15 mm
Z = 8

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Data collection

Bruker SMART CCD area-detector diffractometer	2969 independent reflections
Radiation source: fine-focus sealed tube	1965 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.043
T = 298(2) K	θ_max = 25.5º
φ and ω scans	θ_min = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −19→34
T_min = 0.926, T_max = 0.965	k = −8→8
8091 measured reflections	l = −21→19

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Refinement

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.066	H-atom parameters constrained
wR(F²) = 0.215	w = 1/[σ²(F_o²) + (0.095P)² + 15.5678P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2969 reflections	Δρ_max = 0.72 e Å⁻³
221 parameters	Δρ_min = −0.29 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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Special details

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.

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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq
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*

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Atomic displacement parameters (Å²)

	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)

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Geometric parameters (Å, °)

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)

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Symmetry codes: (i) −x+3/2, −y+3/2, −z; (ii) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.572 (5)	147

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2322).

References

Bruker (1998). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
Butcher, R. J., Basu Baul, T. S., Singh, K. S. & Smith, F. E. (2005). Acta Cryst. E61, o1007–o1009.
Cai, Y.-Q., Peng, Y.-Q. & Song, G.-H. (2006). Catal. Lett.109, 61–64.
Peng, Y.-Q. & Song, G.-H. (2006). Catal. Commun.8, 111–114.
Pradeep, C. P. (2005). Acta Cryst. E61, o3825–o3827.
Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037124/tk2322sup1.cif

e-64-o2365-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037124/tk2322Isup2.hkl

e-64-o2365-Isup2.hkl^{(145.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[bb1] Bruker (1998). SMART Bruker AXS Inc., Madison, Wisconsin, USA.

[bb2] Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.

[bb3] Butcher, R. J., Basu Baul, T. S., Singh, K. S. & Smith, F. E. (2005). Acta Cryst. E61, o1007–o1009.

[bb4] Cai, Y.-Q., Peng, Y.-Q. & Song, G.-H. (2006). Catal. Lett.109, 61–64.

[bb5] Peng, Y.-Q. & Song, G.-H. (2006). Catal. Commun.8, 111–114.

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1-{2-[(2-hydroxybenzylidene)-amino]-ethyl}-3-methyl-3H-imidazolium hexafluorophosphate

Bin Li

Yi-Qun Li

Yue-Peng Cai

Mei-Yun Zhou

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Table 1. Hydrogen-bond geometry (Å, °).

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)

Geometric parameters (Å, °)

Hydrogen-bond geometry (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

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PERMALINK

1-{2-[(2-hydroxybenzylidene)-amino]-ethyl}-3-methyl-3H-imidazolium hexafluorophosphate

Bin Li

Yi-Qun Li

Yue-Peng Cai

Mei-Yun Zhou

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Table 1. Hydrogen-bond geometry (Å, °).

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

Atomic displacement parameters (Å2)

Geometric parameters (Å, °)

Hydrogen-bond geometry (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

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Cited by other articles

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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)