The crystal data and experimental parameters used for the intensity data collection. Procedure and final results of the structure determination.
Abstract
[C17H22N2]3[P6O18][H2O]8., a new organic cyclohexaphosphate, was synthesized as single crystals and grown by solution growth method. The crystal structure of the grown product was determined by single crystal X-ray diffraction analysis. The title material crystallized in the monoclinic system of the C2/c space group. The P6O186− ring anions and some water molecules form layers spreading around (b, c) planes via O-H…O hydrogen bonds. Between these inorganic layers are anchored organic cations, which establish H-bonds to interconnect the different adjacent layers and so contribute to the cohesion of the three dimensional lattice. The organic and inorganic rings adopt a chair conformation with different geometrical characteristics due to their different size and flexibility. The title compound was further characterized by FT-IR and NMR spectroscopy.
Keywords
- cyclohexaphosphate
- crystal structure
- inorganic layers
- three dimensional lattice
1. Introduction
Since the preparation and identification of Li6P6O18.6H2O [1], this salt was used as starting reagent to prepare other cyclohexaphosphates. These latters were of great interest in academic and industrial areas over recent years owing to their diversities [2, 3]. Among these compounds, organic cyclohexaphosphates are particularly interesting. Both H-bonds and the organic units are responsible in the organization of such materials as to build inorganic lattices with different features: ribbons [4], two-dimensional lattices [5, 6, 7], and three-dimensional lattices [8, 9]. To study the effect on the chemical and structural geometries, we report and discuss in the present work the results of a structural investigation concerning a new organic-cation cyclohexaphosphate [C17H22N2]3[P6O18][H2O]8. This latter was also characterized by IR and NMR spectroscopy.
The selected organic molecule, 1-(diphenylmethyl)piperazine, is a biogenic diamine, which plays an important role as a deprotonated cation in biological systems [10, 11].
2. Chemical preparation
Based in previous work, the LiH2PO4 [12] and Li6P6O18.6H2O [13] salts were synthesized first. Then, the title compound was prepared by adding cyclohexaphosphoric acid dropwise, produced from Li6P6O18.6H2O through a cation-exchange resin (Amberlite IR 120) into an ethalonic solution of 1-(diphenylmethyl)piperazine. The obtained solution was stirred for few minutes and allowed to a slow solvent evaporation at room temperature until stable crystals of [C17H22N2]3[P6O18][H2O]8 with suitable dimensions were obtained.
3. Structure description
Crystal data and details of structure refinement are summarized in Table 1. Molecular graphics were performed employing Diamond [14]. The chemical composition of [C17H22N2]3[P6O18][H2O]8 includes three entities, one phosphoric ring, eight water molecules and three crystallographically distinct organic cations. An ORTEP view of the geometrical configuration of these entities is depicted in Figure 1, while Figure 2 exhibits the complete atomic arrangement. The packing of the title compound consists of hybrid layers where the organic and inorganic species are alternated. Theses layers, extended perpendicularly to the b-axis, are also connected by H-bonds in the two other directions assuring the cohesion of the lattice.
Empirical formula | C51H82N6O26P6 |
---|---|
Formula weight [g mol−1] | 1381.04 |
Crystal color, habit | colorless, rod |
Crystal temperature [K] | 295 |
Crystal size [mm3] | 0.15 × 0.23 × 0.49 |
Radiation, wavelength [Å] | Mo |
Crystal system | Monoclinic |
Space group | C2/c |
Unit-cell dimensions: | |
36.0432(10), 12.9785(4), 34.1510(9) | |
118.7840(8) | |
Volume [Å3] | 14001.5(7) |
Z | 8 |
Density calc. [g cm−3] | 1.310 |
Reflections for cell determination | 26,969 |
θ range for cell determination [°] | 2 to 27 |
Absorption coefficient μ [mm−1] | 0.232 |
F(000) | 5824 |
θ-Range for data collection [°] | 1.289 to 26.999 |
Limiting indices | −45 ≤ h ≤ 46, −16 ≤ k ≤ 15, −43 ≤ l ≤ 43 |
Reflections collected/unique | 26,969, 10,651 ( |
Refinement method | Full-matrix least-squares on |
Data, restrains, parameters (I > 2 σ) | 15,155, 24, 851 |
Goodness-of-fit on | 1.094 |
R indices (all data, on | R = 0.0663, Rw = 0.2133 |
A chair conformation for the P6O18 ring anion was adopted (Figure 3-a). This phosphoric ring includes six independent PO4 tetrahedra. The values of the P∙O∙P, O∙P∙O angles and the P∙O and O∙O distances, are listed in Table 2. The P∙O bond lengths vary between 1.457 and 1.612 Å with an average value of 1.534 Å. The variation of the environment around the oxygen atoms can explains this divergence. Despite this diversity in P∙O distances, each tetrahedron in the P6O18 anion can be represented by typical O atoms arrangement with phosphorus atom moved of 0.117, 0.134, 0.138, 0.134, 0.147, 0.147 Å from the centre (Table 3, Figure 3-a). In addition, the distortion indices (DI) [15]: DI(PO) = 0.039, DI(OPO) = 0.038 and DI(OO) = 0.014 show an above distortion of the O-O bond lengths compared to P-O and O-P-O ones as illustrated in Table 3.
P1 | O1 | O6 | O7 | O8 |
O1 | 1.596(2) | 103.49(16) | 106.27(13) | 108.74(15) |
O6 | 2.491(0) | 1.576(3) | 111.97(15) | 106.60(15) |
O7 | 2.458(0) | 2.530(0) | 1.475(2) | 118.70(15) |
O8 | 2.501(0) | 2.451(0) | 2.541(0) | 1.479(2) |
P2 | O1 | O2 | O9 | O10 |
O1 | 1.599(2) | 100.68(15) | 111.09(14) | 108.85(17) |
O2 | 2.454(1) | 1.589(2) | 105.57(14) | 110.48(17) |
O9 | 2.541(1) | 2.445(1) | 1.481(2) | 118.64(18) |
O10 | 2.495(1) | 2.511(1) | 2.535(1) | 1.467(3) |
P3 | O2 | O3 | O11 | O12 |
O2 | 1.604(2) | 100.96(16) | 110.90(15) | 106.44(16) |
O3 | 2.470(0) | 1.597(3) | 107.62(15) | 109.90(18) |
O11 | 2.539(0) | 2.481(0) | 1.476(3) | 119.46(17) |
O12 | 2.465(0) | 2.513(0) | 2.546(0) | 1.471(3) |
P4 | O3 | O4 | O13 | O14 |
O3 | 1.601(3) | 102.1(2) | 106.09(17) | 110.70(16) |
O4 | 2.472(0) | 1.579(3) | 111.23(19) | 104.78(17) |
O13 | 2.455(0) | 2.517(0) | 1.470(3) | 120.52(17) |
O14 | 2.539(0) | 2.428(0) | 2.565(0) | 1.484(3) |
P5 | O4 | O5 | O15 | O16 |
O4 | 1.593(3) | 98.30(18) | 111.44(17) | 107.9(2) |
O5 | 2.404(0) | 1.586(3) | 107.85(14) | 110.12(18) |
O15 | 2.536(0) | 2.508(0) | 1.475(2) | 119.24(17) |
O16 | 2.479(0) | 2.542(0) | 2.474(0) | 1.473(3) |
P6 | O5 | O6 | O17 | O18 |
O5 | 1.612(3) | 110.93(16) | 108.42(18) | 110.93(16) |
O6 | 2.464(0) | 1.596(3) | 109.45(19) | 105.94(18) |
O17 | 2.491(0) | 2.494(0) | 1.457(3) | 119.93(19) |
O18 | 2.551(0) | 2.460(0) | 2.546(0) | 1.483(3) |
P1-P2 | 2.893(2) | P1-O1-P2 | 129.73(3 | P1-P2-P3 | 114.21(2) |
P2-P3 | 2.956(2) | P2-O2-P3 | 135.52(3) | P2-P3-P4 | 103.08(2) |
P3-P4 | 2.931(2) | P3-O3-P4 | 132.9(3) | P3-P4-P5 | 110.47(2) |
P4-P5 | 2.954(2) | P4-O4-P5 | 137.24(3) | P4-P5-P6 | 110.01(2) |
P5-P6 | 2.909(2) | P5-O5-P6 | 130.97(3) | P5-P6-P1 | 104.39(2) |
P6-P1 | 2.982(2) | P6-O6-P1 | 140.09(3) | P6-P1-P2 | 103.58(2) |
Tetrahedron | P-Om | ID (P-O) | (O-P-O)m | ID (OPO) | O-Om | ID (O-O) | δ |
---|---|---|---|---|---|---|---|
P1(O4) | 1.532 | 0.036 | 109.295 | 0.037 | 2.495 | 0.011 | 0.117 |
P2(O4) | 1.534 | 0.039 | 109.251 | 0.038 | 2.497 | 0.013 | 0.134 |
P3(O4) | 1.537 | 0.041 | 109.213 | 0.039 | 2.502 | 0.012 | 0.138 |
P4(O4) | 1.534 | 0.037 | 109.236 | 0.045 | 2.496 | 0.017 | 0.134 |
P5(O4) | 1.532 | 0.038 | 109.141 | 0.041 | 2.491 | 0.015 | 0.147 |
P6(O4) | 1.537 | 0.044 | 110.93 | 0.027 | 2.501 | 0.013 | 0.147 |
The P-O-P angle values match well with those noticed in others cyclohexaphoshates [16, 17]. But the P1-O6-P6 angle of 140.09°, diverge from the value generally observed in such anions. This angle induces a longer P–P distance (2.982°). It should be signaled that these values display the greatest discrepancy measured until now. The P–P–P angles ranging from 103.08 to 114.21° which averages are 107.62°, show large deviations from the ideal value (120°). In spite of this variance, the distortion is more important if compared with that observed in [C9H14N]4[H3O]2[P6O18] [18] with the same space C2\c group in which the average of the P–P–P angle is 101.0°.
In the crystal structure there are three independent 1-(diphenylmethyl)piperazinium cations that are associated with phosphoric entities through electrostatic interactions and hydrogen bonds involving hydrogen atoms of NH and NH2. Each six-membered piperazinedium ring adopts a chair conformation (Figure 3-b). In all hydrogen bonds, the nitrogen atoms are donors, whereas the oxygen from the P6O186− acts as acceptor atoms (Table 4), with N…O separations ranging from 2.6354 to 2.9864 Å. The (N-C, C-C) bond lengths and bond angles (N-C-C, C-C-C) ranging from 1.346(9) to 1.528(4) Å and from 108.4(3) to 124.6(4) ° (Table 5) are comparable with those observed in other organic phosphates [19].
N(1)-H(1)…O(7) | 0.98 | 1.70 | 2.6681 | 168 |
N(2)-H(2A)…O(11) | 0.89 | 1.90 | 2.7200 | 152 |
N(2)-H(2B)…O(15) | 0.89 | 1.93 | 2.7408 | 151 |
N(3)-H(3)…O(8) | 0.98 | 1.68 | 2.6354 | 164 |
N(4)-H(4C)…O(2) | 0.89 | 2.59 | 2.9864 | 108 |
N(4)-H(4C)…O(9) | 0.89 | 1.84 | 2.7231 | 170 |
N(4)-H(4D)…O(14) | 0.89 | 1.89 | 2.7444 | 161 |
N(5)-H(5)…O(10) | 0.98 | 1.69 | 2.6560 | 166 |
N(6)-H(6A)…O(16) | 0.89 | 1.98 | 2.7625 | 147 |
N(6)-H(6B)…O(1 W) | 0.89 | 1.85 | 2.6998 | 159 |
C(1)-H(1B)…O(13) | 0.97 | 2.43 | 3.3031 | 149 |
C(3)-H(3A)…O(1) | 0.97 | 2.54 | 3.4332 | 153 |
C(4)-H(4A)…O(15) | 0.97 | 2.58 | 3.2464 | 126 |
C(5)-H(5A)…O(13) | 0.98 | 2.44 | 3.3306 | 150 |
C(7)-H(7)…O(7) | 0.93 | 2.38 | 3.2627 | 158 |
C(13)-H(13)…O(7) | 0.93 | 2.59 | 3.4217 | 150 |
C(19)-H(19A)…O(9) | 0.97 | 2.60 | 3.3733 | 137 |
C(20)-H(20B) ..O(6) | 0.97 | 2.46 | 3.3110 | 147 |
C(22)-H(22) ..O(10 W) | 0.98 | 2.52 | 3.4419 | 156 |
C(30)-H(30) ..O(8) | 0.93 | 2.53 | 3.3191 | 142 |
C(35)-H(35A) ..O(18) | 0.97 | 2.59 | 3.4981 | 156 |
C(37)-H(37A) ..O(11) | 0.97 | 2.50 | 3.3556 | 148 |
C(37)-H(37B) ..O(8 W) | 0.97 | 2.56 | 3.1961 | 123 |
C(39)-H(39) ..O(17) | 0.98 | 2.40 | 3.3125 | 154 |
[C17H22N2(1)]+ group | |||||
N1 - C4 | 1.499(4) | C4 - N1 - C1 | 108.7(3) | ||
N1 - C1 | 1.506(4) | C4 - N1 - C5 | 110.6(2) | ||
N1 - C5 | 1.528(4) | C1 - N1 - C5 | 111.4(2) | ||
N2 - C2 | 1.478(4) | C2 - N2 - C3 | 110.7(3) | ||
N2 - C3 | 1.483(4) | N1 - C1 - C2 | 110.9(3) | ||
C1 - C2 | 1.514(5) | N2 - C2 - C1 | 111.4(3) | ||
C3 - C4 | 1.495(4) | N2 - C3 - C4 | 110.6(3) | ||
C5 - C6 | 1.510(5) | C3 - C4 - N1 | 110.3(3) | ||
C5 - C12 | 1.521(5) | C6 - C5 - C12 | 111.1(3) | ||
C6 - C11 | 1.388(5) | C6 - C5 - N1 | 113.1(3) | ||
C6 - C7 | 1.389(5) | C12 - C5 - N1 | 110.0(3) | ||
C7 - C8 | 1.395(5) | C11 - C6 - C7 | 118.5(4) | ||
C8 - C9 | 1.378(8) | C11 - C6 - C5 | 117.5(4) | ||
C9 - C10 | 1.368(8) | C7 - C6 - C5 | 123.4(3) | ||
C10 - C11 | 1.385(7) | C6 - C7 - C8 | 120.7(4) | ||
C12 - C17 | 1.382(5) | C9 - C8 - C7 | 120.1(5) | ||
C12 - C13 | 1.399(5) | C10 - C9 - C8 | 119.4(4) | ||
C13 - C14 | 1.374(6) | C9 - C10 - C11 | 121.2(5) | ||
C14 - C15 | 1.382(7) | C10 - C11 - C6 | 120.2(5) | ||
C15 - C16 | 1.399(7) | C17 - C12 - C13 | 119.1(3) | ||
C16 - C17 | 1.375(6) | C17 - C12 - C5 | 119.5(3) | ||
C9 - C10 - C11 | 121.2(5) | ||||
C10 - C11 - C6 | 120.2(5) | ||||
C13 - C12 - C5 | 121.4(3) | ||||
C14 - C13 - C12 | 120.4(4) | ||||
C13 - C14 - C15 | 120.3(4) | ||||
C14 - C15 - C16 | 119.6(4) | ||||
C17 - C16 - C15 | 119.9(4) | ||||
C16 - C17 - C12 | 120.7(4) | ||||
[C17H22N2(2)]+ group | |||||
N3 - C18 | 1.496(4) | C18 - N3 - C21 | 109.3(3) | ||
N3 - C21 | 1.496(4) | C18 - N3 - C22 | 110.3(3) | ||
N3 - C22 | 1.521(4) | C21 - N3 - C22 | 110.8(3) | ||
N4 - C20 | 1.473(5) | C20 - N4 - C19 | 110.6(3) | ||
N4 - C19 | 1.482(5) | N3 - C18 - C19 | 111.1(3) | ||
C18 - C19 | 1.509(5) | N4 - C19 - C18 | 110.3(3) | ||
C20 - C21 | 1.514(5) | N4 - C20 - C21 | 110.0(3) | ||
C22 - C29 | 1.511(5) | N3 - C21 - C20 | 111.9(3) | ||
C22 - C23 | 1.523(5) | C29 - C22 - N3 | 112.3(3) | ||
C23 - C24 | 1.382(5) | C29 - C22 - C23 | 110.4(3) | ||
C23 - C28 | 1.396(5) | N3 - C22 - C23 | 112.9(3) | ||
C24 - C25 | 1.395(6) | C24 - C23 - C28 | 118.4(4) | ||
C25 - C26 | 1.369(6) | C24 - C23 - C22 | 123.2(3) | ||
C26 - C27 | 1.388(7) | C28 - C23 - C22 | 118.2(3) | ||
C29 - C34 | 1.357(6) | C23 - C24 - C25 | 120.0(4) | ||
C29 - C30 | 1.401(6) | C26 - C25 - C24 | 120.6(4) | ||
C30 - C31 | 1.387(6) | C25 - C26 - C27 | 119.4(4) | ||
C31 - C32 | 1.346(9) | C28 - C27 - C26 | 120.3(4) | ||
C32 - C33 | 1.382(10) | C27 - C28 - C23 | 121.3(4) | ||
C33 - C34 | 1.367(8) | C34 - C29 - C30 | 118.2(4) | ||
C34 - C29 - C22 | 119.8(4) | ||||
C30 - C29 - C22 | 121.8(3) | ||||
C31 - C30 - C29 | 119.8(5) | ||||
C32 - C31 - C30 | 120.1(6) | ||||
C31 - C32 - C33 | 120.7(5) | ||||
C34 - C33 - C32 | 119.1(5) | ||||
C29 - C34 - C33 | 122.1(6) | ||||
[C17H22N2(3)]+ group | |||||
N5 - C35 | 1.501(5) | C35 - N5 - C38 | 108.4(3) | ||
N5 - C38 | 1.508(5) | C35 - N5 - C39 | 111.6(3) | ||
N5 - C39 | 1.526(4) | C38 - N5 - C39 | 109.5(3) | ||
N6 - C37 | 1.472(5) | C37 - N6 - C36 | 110.5(3) | ||
N6 - C36 | 1.480(6) | C36 - C35 - N5 | 111.5(3) | ||
C35 - C36 | 1.490(6) | N6 - C36 - C35 | 112.0(3) | ||
C37 - C38 | 1.506(6) | N6 - C37 - C38 | 110.6(4) | ||
C39 - C40 | 1.511(5) | C37 - C38 - N5 | 111.6(3) | ||
C39 - C46 | 1.525(5) | C40 - C39 - C46 | 113.2(3) | ||
C40 - C41 | 1.387(6) | C40 - C39 - N5 | 111.8(3) | ||
C40 - C45 | 1.394(6) | C46 - C39 - N5 | 110.8(3) | ||
C41 - C42 | 1.376(7) | C41 - C40 - C45 | 118.0(4) | ||
C42 - C43 | 1.385(8) | C41 - C40 - C39 | 117.4(4) | ||
C43 - C44 | 1.372(7) | C45 - C40 - C39 | 124.6(4) | ||
C44 - C45 | 1.374(6) | C42 - C41 - C40 | 120.9(4) | ||
C46 - C47 | 1.379(5) | C41 - C42 - C43 | 120.2(5) | ||
C46 - C51 | 1.390(5) | C44 - C43 - C42 | 119.5(5) | ||
C47 - C48 | 1.397(6) | C43 - C44 - C45 | 120.4(5) | ||
C48 - C49 | 1.366(8) | C44 - C45 - C40 | 121.0(4) | ||
C49 - C50 | 1.370(7) | C47 - C46 - C51 | 118.8(4) | ||
C50 - C51 | 1.394(6) | C47 - C46 - C39 | 118.0(3) | ||
C51 - C46 - C39 | 123.1(3) | ||||
C46 - C47 - C48 | 120.0(4) | ||||
C49 - C48 - C47 | 121.0(4) | ||||
C48 - C49 - C50 | 119.3(4) | ||||
C49 - C50 - C51 | 120.6(4) | ||||
C46 - C51 - C50 | 120.3(4) | ||||
N1 - H1 | 0.9800 | N3 - H3 | 0.9800 | N5 - H5 | 0.9800 |
N2 - H2A | 0.8900 | N4 - H4C | 0.8900 | N6 - H6A | 0.8900 |
N2 - H2B | 0.8900 | N4 - H4D | 0.8900 | N6 - H6B | 0.8900 |
H2A - N2 - H2B | 108.1 | ||||
H4C - N4 - H4D | 108.1 | ||||
H6A - N6 - H6B | 108.1 |
It must be noted that: Firstly, all water molecules are not involved in the inorganic layers which may explain their high thermal factors. Such thermal factor values were observed too in others similar structures [20, 21]. Secondly and except O(1 W) and O(2 W), the others water molecules have a static disorder, being split into two fragments with an occupancy rates of 0.5.
4. Conclusion
Along this work, a new [C17H22N2]3[P6O18][H2O]8 organic cyclohexaphosphate has been successfully synthesized and grown by solution growth method at ambient temperature. According to the X-ray structural results, the crystal structure is governed by hydrogen bonding and intermolecular interactions, resulting infinite inorganic and organic layers. This analysis indicated that the PO4 tetrahedra possessed a slightly distorted geometry. The P1-O6-P6 angle of 140.09°, depart significantly from the value generally observed in such anions and The P–P–P angles ranging from 103.08 to 114.21° which averages are 107.62°, show large deviations from the ideal value (120°). The title compound was further characterized by FT-IR NMR spectroscopy and DFT calculation.
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