(±)-Bis(1-carb­oxy-2-phenyl­ethanaminium) hexa­fluoro­silicate(VI)

Belhouas, R.; Bouacida, S.; Boudaren, C.; Daran, J.-C.; Roisnel, T.

doi:10.1107/S1600536812021587

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1791-o1792

doi:10.1107/S1600536812021587

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(±)-Bis(1-carboxy-2-phenylethanaminium) hexafluorosilicate(VI)

Ratiba Belhouas,^a Sofiane Bouacida,^a ^* Chaouki Boudaren,^a Jean-Claude Daran ^b and Thierry Roisnel ^c

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Université Mentouri-Constantine, 25000 Algeria, ^bLaboratoire de Chimie de Coordination, UPR CNRS 8241, 205 route de Narbonne, 31077 Toulouse Cedex, France, and ^cCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 18 April 2012; accepted 12 May 2012; online 19 May 2012)

The asymmetric unit of the title fluorosilicate salt, 2C₉H₁₂NO₂⁺·SiF₆²⁻, consists of a phenylalaninium cation and half of a fluorosilicate anion, the Si atom being located on an inversion center. In the crystal, all of the F atoms act as hydrogen-bond acceptors and link the cations through different graph-set motifs, forming layers developing parallel to (100).

Related literature

For applications of fluorosilicate salts, see: Katayama et al. (2001 ); Kalem (2004 ); Airoldi & De Farias (2000 ); Han et al. (2000 ); Gelmboldt (1989 ); Gelmboldt et al. (2007 ). For our previous work on hydrogen-bonding interactions in the crystal structures of protonated amines, see: Bouacida et al. (2005 , 2007 , 2009 ); Benslimane et al. (2007 ); Bouacida (2008 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For hydrogen-bond motifs, see: Etter et al. (1990 ); Bernstein et al. (1995 ); Janiak (2000 ).

Experimental

Crystal data

2C₉H₁₂NO₂⁺·SiF₆²⁻
M_r = 474.48
Monoclinic, P 2₁ /c
a = 11.183 (2) Å
b = 5.7531 (10) Å
c = 17.000 (4) Å
β = 105.59 (2)°
V = 1053.5 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 295 K
0.59 × 0.50 × 0.37 mm

Data collection

Nonius KappaCCD diffractometer
2412 measured reflections
2412 independent reflections
1917 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.086
S = 1.03
2412 reflections
144 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯F2ⁱ	0.82	1.84	2.6456 (14)	167
N2—H2A⋯O2ⁱⁱ	0.89	2.04	2.8511 (17)	151
N2—H2B⋯F3	0.89	1.88	2.7656 (15)	171
N2—H2C⋯F1ⁱⁱⁱ	0.89	2.01	2.8549 (15)	158
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z.

Data collection: COLLECT (Otwinowski & Minor, 1997 ); cell refinement: DIRAX/LSQ (Duisenberg et al., 2003 ); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021587/ez2295sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021587/ez2295Isup2.hkl

checkCIF report

Comment top

Fluorosilicate salts involving onium cations of N– and O– containing organic bases and amino acids have practical applications as ionic liquids (Katayama et al., 2001), dielectrics with cryptocrystalline structure (Kalem, 2004), layered organic-inorganic hybrid materials (Airoldi & De Farias, 2000) and chemical reagents (Han et al., 2000; Gelmboldt, 1989). Their structures are commonly dominated by strong directional interactions involving F atoms and convenient hydrogen-bond donors, although the relationships in such systems can be complicated due to the presence of competitive OH and NH binding sites (Gelmboldt et al., 2007). We report here the synthesis, crystal structure and hydrogen-bonded frameworks of a new hybrid compound based on fluorosilicate. The title compound (I) was prepared as part of our ongoing studies of hydrogen-bonding interactions in the crystal structures of protonated amines (Bouacida et al., 2005, 2007, 2009; Benslimane et al., 2007; Bouacida, 2008). From the molecular point of view, the structure is quite simple, since the individual components do not deviate from the expected geometries, with bond distances and angles lying within reported values for these species (CSD, Allen, 2002). The most attractive aspect of these structures resides in their extensive hydrogen-bonding schemes.

The asymmetric unit of (I) is built up from a (+/-)-phenylalaninium cation and half a molecule of a hexafluorosilicate anion located on an inversion center, connected by N—H···F hydrogen bonds (Fig. 1).

As observed in compound I, all the F atoms of the hexafluorosilicate anion act as hydrogen bond acceptors and are engaged in N—H···F and O—H···F bonds with the alaninium part of the cation (Fig. 2, Table 1). Two H atoms, H2B and H2C and their symmetry related counterparts (-x, -y, 1 - z), of the ammonium NH₃ interact with two symmetry related fluorosilicate (-x, -y, 1 - z) building a R₄²(8) ring labelled B1, whereas H2A, the third H atom of the NH₃ and the H atom of the symmetry related (-x, y + 1/2, -z + 1/2) carboxylate complete a R₃³(10) graph set motif labelled B2. Futhermore, two symmetry related (-x, y - 1/2, 1/2 - z) cations and one fluorosilicate (x, y - 1, z) form a R₃³ (14) ring labelled B3, through N2—H2C···F1, N2—H2B···O2 and O1—H···F2 (Etter et al., 1990; Bernstein et al., 1995), see Table 1, Fig. 2.

These hydrogen bonds result in the formation of layers parallel to the (1 0 0) plane. In these layers, chains of cations and anions alternate (Fig. 3). As shown in the Figure, the phenyl rings of the symmetry related layers are intercalated; however the centroid to centroid distance between the phenyl rings are too long (4.958 (1) and 4.523 (1) Å) to consider π-π interactions (Janiak, 2000).

Related literature top

For applications of fluorosilicate salts, see: Katayama et al. (2001); Kalem (2004); Airoldi & De Farias (2000); Han et al. (2000); Gelmboldt (1989); Gelmboldt et al. (2007). For our previous work on hydrogen-bonding interactions in the crystal structures of protonated amines, see: Bouacida et al. (2005, 2007, 2009); Benslimane et al. (2007); Bouacida (2008). For a description of the Cambridge Structural Database, see: Allen (2002). For hydrogen-bond motifs, see: Etter et al. (1990); Bernstein et al. (1995); Janiak (2000).

Experimental top

Crystals of compound I were grown from an aqueous solution that was obtained by dissolving 1 mmol SiO₂ and 2 mmol phenylalanine in hydrofluoric acid (HF). The solutions were slowly evaporated to dryness for a couple of weeks. Some white crystals were carefully isolated under polarizing microscope for analysis by X-ray diffraction.

Computing details top

Data collection: COLLECT (Otwinowski & Minor, 1997); cell refinement: DIRAX/LSQ (Duisenberg et al., 2003); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The asymmetric unit of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bond is shown as dashed line.[Symmetry codes: (i) -x, 1 - y, 1 - z]
	Fig. 2. Partial view of compound (I), showing the formation of R₄²(8) (B1), R₃³(10) (B2) and R₃³(14) (B3) graph set motifs through N—H···F, N—H···O and O—H···F hydrogen bonds. The C₆H₅CH₂ fragment have been omitted for the sake of clarity. [Symmetry codes: (i) -x, y - 1/2, -z + 1/2; (ii) -x, y + 1/2, -z + 1/2; (iii) x, y - 1, z; (iv) -x, -y, -z + 1; (v) -x, y - 1/2, 1/2 - z]
	Fig. 3. Packing view projected down the b axis showing the formation of layers parallel to the (1 0 0) plane. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

(±)-Bis(1-carboxy-2-phenylethanaminium) hexafluorosilicate(VI) top

Crystal data top

2C₉H₁₂NO₂⁺·SiF₆²⁻	F(000) = 492
M_r = 474.48	D_x = 1.496 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4769 reflections
a = 11.183 (2) Å	θ = 5.0–27.5°
b = 5.7531 (10) Å	µ = 0.19 mm⁻¹
c = 17.000 (4) Å	T = 295 K
β = 105.59 (2)°	Block, white
V = 1053.5 (4) Å³	0.59 × 0.50 × 0.37 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	1917 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 27.5°, θ_min = 5.0°
Detector resolution: 9 pixels mm^-1	h = −14→13
CCD rotation images, thick slices scans	k = 0→7
2412 measured reflections	l = 0→22
2412 independent reflections

Refinement top

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0329P)² + 0.2833P] where P = (F_o² + 2F_c²)/3
2412 reflections	(Δ/σ)_max = 0.001
144 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

2C₉H₁₂NO₂⁺·SiF₆²⁻	V = 1053.5 (4) Å³
M_r = 474.48	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.183 (2) Å	µ = 0.19 mm⁻¹
b = 5.7531 (10) Å	T = 295 K
c = 17.000 (4) Å	0.59 × 0.50 × 0.37 mm
β = 105.59 (2)°

Data collection top

Nonius KappaCCD diffractometer	1917 reflections with I > 2σ(I)
2412 measured reflections	R_int = 0.000
2412 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.03	Δρ_max = 0.22 e Å⁻³
2412 reflections	Δρ_min = −0.19 e Å⁻³
144 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Si1	0.0000	0.5000	0.5000	0.02345 (13)
F1	0.07812 (8)	0.54094 (14)	0.43002 (5)	0.0345 (2)
F2	−0.11419 (8)	0.36774 (15)	0.42781 (5)	0.0371 (2)
F3	0.07100 (8)	0.24091 (13)	0.52540 (5)	0.0346 (2)
O1	0.17794 (11)	0.0905 (2)	0.21347 (6)	0.0403 (3)
H1	0.1700	0.0176	0.1709	0.060*
O2	0.10064 (12)	−0.23340 (19)	0.25348 (6)	0.0431 (3)
N2	0.05617 (12)	0.0158 (2)	0.37935 (7)	0.0307 (3)
H2A	−0.0126	0.0728	0.3455	0.046*
H2B	0.0661	0.0763	0.4289	0.046*
H2C	0.0499	−0.1381	0.3820	0.046*
C2	0.16410 (14)	0.0759 (2)	0.34897 (8)	0.0293 (3)
H2	0.1696	0.2449	0.3435	0.035*
C1	0.14352 (13)	−0.0392 (2)	0.26636 (8)	0.0289 (3)
C3	0.28085 (15)	−0.0161 (3)	0.41120 (9)	0.0410 (4)
H3A	0.2872	0.0580	0.4634	0.049*
H3B	0.2708	−0.1816	0.4182	0.049*
C4	0.40009 (15)	0.0225 (3)	0.38861 (9)	0.0374 (4)
C6	0.55760 (19)	−0.1169 (4)	0.32857 (12)	0.0563 (5)
H6	0.5865	−0.2308	0.2994	0.068*
C9	0.47022 (18)	0.2226 (3)	0.41237 (11)	0.0493 (4)
H9	0.4405	0.3395	0.4399	0.059*
C8	0.58322 (19)	0.2497 (4)	0.39562 (12)	0.0585 (5)
H8	0.6297	0.3835	0.4124	0.070*
C5	0.44501 (17)	−0.1453 (3)	0.34602 (11)	0.0469 (4)
H5	0.3988	−0.2791	0.3289	0.056*
C7	0.62729 (18)	0.0799 (4)	0.35423 (12)	0.0580 (5)
H7	0.7041	0.0975	0.3435	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0314 (3)	0.0221 (2)	0.0178 (2)	−0.0039 (2)	0.00823 (19)	−0.00049 (18)
F1	0.0451 (5)	0.0334 (4)	0.0310 (4)	−0.0022 (4)	0.0206 (4)	0.0025 (3)
F2	0.0414 (5)	0.0393 (5)	0.0281 (4)	−0.0112 (4)	0.0049 (4)	−0.0044 (3)
F3	0.0472 (5)	0.0277 (4)	0.0311 (4)	0.0050 (4)	0.0141 (4)	0.0041 (3)
O1	0.0516 (7)	0.0483 (6)	0.0232 (5)	−0.0117 (5)	0.0137 (5)	−0.0002 (4)
O2	0.0606 (8)	0.0396 (6)	0.0310 (5)	−0.0123 (5)	0.0156 (5)	−0.0066 (5)
N2	0.0388 (7)	0.0284 (6)	0.0283 (6)	0.0025 (5)	0.0147 (5)	0.0024 (5)
C2	0.0359 (8)	0.0285 (7)	0.0252 (6)	−0.0043 (6)	0.0110 (6)	−0.0002 (5)
C1	0.0274 (7)	0.0352 (8)	0.0238 (6)	0.0002 (6)	0.0065 (5)	0.0010 (5)
C3	0.0388 (9)	0.0543 (10)	0.0265 (7)	−0.0026 (7)	0.0031 (6)	0.0038 (7)
C4	0.0324 (8)	0.0468 (9)	0.0280 (7)	−0.0026 (7)	−0.0003 (6)	0.0029 (6)
C6	0.0453 (11)	0.0653 (12)	0.0589 (11)	0.0071 (9)	0.0150 (9)	−0.0007 (9)
C9	0.0484 (11)	0.0497 (10)	0.0441 (9)	−0.0052 (8)	0.0027 (8)	−0.0041 (8)
C8	0.0491 (12)	0.0588 (12)	0.0586 (11)	−0.0176 (10)	−0.0009 (9)	0.0077 (10)
C5	0.0412 (10)	0.0472 (10)	0.0502 (10)	−0.0055 (8)	0.0088 (8)	−0.0044 (7)
C7	0.0349 (10)	0.0765 (14)	0.0596 (11)	−0.0056 (10)	0.0071 (9)	0.0138 (10)

Geometric parameters (Å, º) top

Si1—F1ⁱ	1.6711 (9)	C2—H2	0.9800
Si1—F1	1.6711 (9)	C3—C4	1.500 (2)
Si1—F3ⁱ	1.6895 (8)	C3—H3A	0.9700
Si1—F3	1.6895 (8)	C3—H3B	0.9700
Si1—F2	1.6952 (8)	C4—C5	1.380 (3)
Si1—F2ⁱ	1.6952 (9)	C4—C9	1.391 (2)
O1—C1	1.3036 (17)	C6—C7	1.377 (3)
O1—H1	0.8200	C6—C5	1.379 (3)
O2—C1	1.2121 (17)	C6—H6	0.9300
N2—C2	1.4760 (18)	C9—C8	1.377 (3)
N2—H2A	0.8900	C9—H9	0.9300
N2—H2B	0.8900	C8—C7	1.371 (3)
N2—H2C	0.8900	C8—H8	0.9300
C2—C1	1.5135 (19)	C5—H5	0.9300
C2—C3	1.537 (2)	C7—H7	0.9300

F1ⁱ—Si1—F1	180.0	O2—C1—O1	125.37 (13)
F1ⁱ—Si1—F3ⁱ	90.38 (4)	O2—C1—C2	121.67 (13)
F1—Si1—F3ⁱ	89.62 (4)	O1—C1—C2	112.95 (12)
F1ⁱ—Si1—F3	89.62 (4)	C4—C3—C2	114.97 (12)
F1—Si1—F3	90.38 (4)	C4—C3—H3A	108.5
F3ⁱ—Si1—F3	180.0	C2—C3—H3A	108.5
F1ⁱ—Si1—F2	90.90 (5)	C4—C3—H3B	108.5
F1—Si1—F2	89.10 (4)	C2—C3—H3B	108.5
F3ⁱ—Si1—F2	90.00 (4)	H3A—C3—H3B	107.5
F3—Si1—F2	90.00 (4)	C5—C4—C9	118.37 (17)
F1ⁱ—Si1—F2ⁱ	89.10 (4)	C5—C4—C3	120.33 (15)
F1—Si1—F2ⁱ	90.90 (5)	C9—C4—C3	121.26 (16)
F3ⁱ—Si1—F2ⁱ	90.00 (4)	C7—C6—C5	120.05 (19)
F3—Si1—F2ⁱ	90.00 (4)	C7—C6—H6	120.0
F2—Si1—F2ⁱ	180.0	C5—C6—H6	120.0
C1—O1—H1	109.5	C8—C9—C4	120.73 (18)
C2—N2—H2A	109.5	C8—C9—H9	119.6
C2—N2—H2B	109.5	C4—C9—H9	119.6
H2A—N2—H2B	109.5	C7—C8—C9	120.13 (18)
C2—N2—H2C	109.5	C7—C8—H8	119.9
H2A—N2—H2C	109.5	C9—C8—H8	119.9
H2B—N2—H2C	109.5	C6—C5—C4	120.84 (17)
N2—C2—C1	106.69 (11)	C6—C5—H5	119.6
N2—C2—C3	107.57 (11)	C4—C5—H5	119.6
C1—C2—C3	112.16 (13)	C8—C7—C6	119.84 (19)
N2—C2—H2	110.1	C8—C7—H7	120.1
C1—C2—H2	110.1	C6—C7—H7	120.1
C3—C2—H2	110.1

N2—C2—C1—O2	−39.96 (18)	C4—C9—C8—C7	0.8 (3)
C3—C2—C1—O2	77.58 (18)	C7—C6—C5—C4	0.5 (3)
N2—C2—C1—O1	140.88 (13)	C9—C4—C5—C6	1.0 (2)
C3—C2—C1—O1	−101.58 (15)	C3—C4—C5—C6	−176.65 (15)
N2—C2—C3—C4	177.95 (13)	C9—C8—C7—C6	0.8 (3)
C1—C2—C3—C4	60.93 (18)	C5—C6—C7—C8	−1.4 (3)
C2—C3—C4—C5	−92.09 (19)	C4—C3—C2—C1	60.93 (18)
C2—C3—C4—C9	90.30 (18)	C4—C3—C2—N2	177.95 (13)
C5—C4—C9—C8	−1.7 (2)	C3—C2—C1—O1	−101.58 (15)
C3—C4—C9—C8	175.98 (15)	C3—C2—C1—O2	77.58 (18)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···F2ⁱⁱ	0.82	1.84	2.6456 (14)	167
N2—H2A···O2ⁱⁱⁱ	0.89	2.04	2.8511 (17)	151
N2—H2B···F3	0.89	1.88	2.7656 (15)	171
N2—H2C···F1^iv	0.89	2.01	2.8549 (15)	158

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

Experimental details

Crystal data
Chemical formula	2C₉H₁₂NO₂⁺·SiF₆²⁻
M_r	474.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.183 (2), 5.7531 (10), 17.000 (4)
β (°)	105.59 (2)
V (Å³)	1053.5 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.59 × 0.50 × 0.37

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2412, 2412, 1917
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.086, 1.03
No. of reflections	2412
No. of parameters	144
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19

Computer programs: COLLECT (Otwinowski & Minor, 1997), DIRAX/LSQ (Duisenberg et al., 2003), EVALCCD (Duisenberg et al., 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···F2ⁱ	0.82	1.84	2.6456 (14)	166.9
N2—H2A···O2ⁱⁱ	0.89	2.04	2.8511 (17)	151.3
N2—H2B···F3	0.89	1.88	2.7656 (15)	171.3
N2—H2C···F1ⁱⁱⁱ	0.89	2.01	2.8549 (15)	158.2

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

Acknowledgements

Thanks are due to MESRS and ANDRU (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et l'Agence Nationale pour le Développement de la Recherche Universitaire - Algérie) for financial support via the PNR programme.

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