organic compounds
Bis(benzylammonium) dihydrogen diphosphate
aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, and bCEMES-CNRS, 29 rue Jeanne Marvig, 31055 Toulouse cedex 4, France
*Correspondence e-mail: samah.akriche@fsb.rnu.tn
The 6H5CH2NH3+·H2P2O72−, contains two independent benzylammonium cations and a dihydrogen diphosphate dianion. In the crystal, O—H⋯O and N—H⋯O hydrogen bonds link the cations and anions, forming a two-dimensional network parallel to (010). Within this network, weak C—H⋯O hydrogen bonds are observed.
of the title salt, 2CCCDC reference: 974273
Related literature
For the chemistry of diphosphate materials, see: Ernester (1992); Lipscomb & Strater (1996); Centi et al. (1988); Chen & Munson (2002); Ballarini et al. (2006). For details of hydrogen bonds, see: Desiraju (1991); Steiner (2002). For related structures, see: Akriche & Rzaigui (2005, 2008); Ahmed et al. (2006); Elboulali et al. (2013).
Experimental
Crystal data
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Data collection: COLLECT (Hooft, 1998); cell DIRAX/LSQ (Duisenberg et al., 2000); 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: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).
Supporting information
CCDC reference: 974273
https://doi.org/10.1107/S1600536813032455/lh5670sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032455/lh5670Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813032455/lh5670Isup3.cml
Prismatic single crystals of the title compound were prepared at room temperature by slow evaporation of a mixture of an aqueous solution (20 ml) of diphosphoric acid (5 mmol) and an ethanolic solution (10 ml) of benzylamine (4 mmol, 0.44 ml). The diphosphoric acid was produced from Na4P2O7 by using a cation-exchange resin (Amberlite IR 120).
All H atoms were placed in calculated positions and treated as riding, with C—H = 0.93 and 0.97 Å respectively for benzene rings and CH2 groups, N—H = 0.89 Å and O—H = 0.82 Å with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(N,O).
There is current interest in the chemistry of diphosphate materials. They are involved in a variety of bioenergetic (Ernester, 1992; Lipscomb & Strater, 1996) and catalytic processes (Centi et al., 1988; Chen et al., 2002; Ballarini et al., 2006). Considering their relevance in several application areas, we are interested in this type of anion in building new hybrid materials associated to organic cations. We report here, the synthesis and the
of the title compound (I).The
of (I) shown in Fig. 1, contains one diphosphate [H2P2O7]2- anion and two crystallographically independent benzylammonium cations. The two PO4 tetrahedral groups are bridged via the O4 bridging oxygen atom with P1—O4—P2 = 133.33 (6)° so as to form the diphosphate anion with a bent configurtation. The conformation is eclipsed evidenced by the psuedo-torsion angle O3—P1···P2—O7 = -6.9°. In the diphosphate group, the longest P—O distances correspond to the bridging oxygen atom with average value d(P—O4) = 1.6104 (8) Å, the intermediate distances are the P—OH bonding [d(P1—O1) = 1.5693 (9) Å, d(P2—O5) = 1.5607 (10) Å], whereas the shortest distances, ranging between 1.4762 (9) Å and 1.4987 (8) Å are related to the terminal oxygen atoms. The average value of the O—P—O angles is 109.25 (5)°. These geometrical features are in same magnitude as observed for diphosphate groups (Akriche et al., 2005; Ahmed et al., 2006; Akriche et al., 2008; Elboulali et al., 2013).In the crystal, O—H···O and N—H···O hydrogen bonds link the cations and anions forming a two-dimensional network parallel to (010) (Table 1 and Fig. 2). Within this network, weak C—H···O hydrogen bonds are observed (Desiraju, 1991; Steiner 2002).
For the chemistry of diphosphate materials, see: Ernester (1992); Lipscomb & Strater (1996); Centi et al. (1988); Chen & Munson (2002); Ballarini et al. (2006). For details of hydrogen bonds, see: Desiraju (1991); Steiner (2002). For related structures, see: Akriche & Rzaigui (2005, 2008); Ahmed et al. (2006); Elboulali et al. (2013).
Data collection: COLLECT (Hooft, 1998); cell
DIRAX/LSQ (Duisenberg et al., 2000); 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: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).Fig. 1. An ORTEP (Farrugia, 2012) view of (I) with displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are represented as dashed lines. | |
Fig. 2. Part of the crystal structure of (I) with hydrogen bonds represented as red dashed lines. The H-atoms not involved in H-bonds are omitted. |
2C7H10N+·H2P2O72− | F(000) = 824 |
Mr = 392.27 | Dx = 1.426 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1337 (2) Å | Cell parameters from 25 reflections |
b = 28.9015 (9) Å | θ = 9–11° |
c = 8.4727 (2) Å | µ = 0.28 mm−1 |
β = 113.449 (1)° | T = 293 K |
V = 1827.24 (9) Å3 | Prism, colourless |
Z = 4 | 0.3 × 0.2 × 0.1 mm |
Nonius KappaCCD diffractometer | 5946 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Detector resolution: 9 pixels mm-1 | θmax = 34.3°, θmin = 2.7° |
CCD rotation images, thick slices scans | h = −12→11 |
27919 measured reflections | k = −45→45 |
7410 independent reflections | l = −13→12 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0651P)2 + 0.3854P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
7410 reflections | Δρmax = 0.52 e Å−3 |
230 parameters | Δρmin = −0.28 e Å−3 |
2C7H10N+·H2P2O72− | V = 1827.24 (9) Å3 |
Mr = 392.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.1337 (2) Å | µ = 0.28 mm−1 |
b = 28.9015 (9) Å | T = 293 K |
c = 8.4727 (2) Å | 0.3 × 0.2 × 0.1 mm |
β = 113.449 (1)° |
Nonius KappaCCD diffractometer | 5946 reflections with I > 2σ(I) |
27919 measured reflections | Rint = 0.025 |
7410 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.52 e Å−3 |
7410 reflections | Δρmin = −0.28 e Å−3 |
230 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.16846 (4) | 0.04396 (2) | 0.78619 (4) | 0.02353 (7) | |
P2 | 0.35638 (4) | −0.03781 (2) | 0.72893 (4) | 0.02459 (8) | |
O1 | 0.27096 (13) | 0.08328 (3) | 0.91571 (12) | 0.0351 (2) | |
H1O1 | 0.3218 | 0.0723 | 1.0123 | 0.053* | |
O2 | 0.05569 (11) | 0.01565 (3) | 0.85084 (12) | 0.03180 (19) | |
O3 | 0.07455 (11) | 0.06475 (3) | 0.61148 (11) | 0.03265 (19) | |
O4 | 0.33579 (11) | 0.01439 (3) | 0.78719 (13) | 0.03276 (19) | |
O5 | 0.25728 (13) | −0.03691 (4) | 0.52889 (12) | 0.0401 (2) | |
H5O5 | 0.1642 | −0.0519 | 0.4998 | 0.060* | |
O6 | 0.55388 (11) | −0.04139 (3) | 0.77466 (12) | 0.0332 (2) | |
O7 | 0.27351 (13) | −0.07023 (4) | 0.81039 (13) | 0.0367 (2) | |
N1 | −0.27361 (14) | 0.05080 (4) | 0.87008 (14) | 0.0304 (2) | |
H1N1 | −0.1667 | 0.0467 | 0.8665 | 0.046* | |
H2N1 | −0.3407 | 0.0258 | 0.8287 | 0.046* | |
H3N1 | −0.2600 | 0.0554 | 0.9784 | 0.046* | |
N2 | −0.16351 (14) | −0.06105 (4) | 0.67481 (15) | 0.0320 (2) | |
H1N2 | −0.1638 | −0.0614 | 0.5697 | 0.048* | |
H2N2 | −0.0859 | −0.0399 | 0.7386 | 0.048* | |
H3N2 | −0.2727 | −0.0541 | 0.6681 | 0.048* | |
C1 | −0.36307 (19) | 0.09184 (5) | 0.76385 (18) | 0.0384 (3) | |
H1A | −0.4815 | 0.0955 | 0.7640 | 0.046* | |
H1B | −0.3769 | 0.0869 | 0.6460 | 0.046* | |
C2 | −0.25602 (19) | 0.13517 (5) | 0.83218 (19) | 0.0372 (3) | |
C3 | −0.1281 (3) | 0.14896 (6) | 0.7728 (3) | 0.0544 (4) | |
H3 | −0.1092 | 0.1318 | 0.6887 | 0.065* | |
C4 | −0.0272 (3) | 0.18878 (8) | 0.8397 (4) | 0.0820 (8) | |
H4 | 0.0598 | 0.1978 | 0.8008 | 0.098* | |
C5 | −0.0551 (4) | 0.21432 (8) | 0.9606 (4) | 0.0865 (8) | |
H5 | 0.0111 | 0.2411 | 1.0026 | 0.104* | |
C6 | −0.1804 (3) | 0.20080 (7) | 1.0213 (3) | 0.0717 (6) | |
H6 | −0.1980 | 0.2183 | 1.1055 | 0.086* | |
C7 | −0.2814 (2) | 0.16112 (6) | 0.9578 (2) | 0.0498 (4) | |
H7 | −0.3662 | 0.1520 | 0.9996 | 0.060* | |
C8 | −0.11012 (18) | −0.10755 (5) | 0.75535 (19) | 0.0381 (3) | |
H8A | −0.1077 | −0.1069 | 0.8707 | 0.046* | |
H8B | 0.0098 | −0.1148 | 0.7643 | 0.046* | |
C9 | −0.23714 (18) | −0.14468 (5) | 0.65266 (18) | 0.0367 (3) | |
C10 | −0.2192 (2) | −0.16351 (7) | 0.5112 (2) | 0.0522 (4) | |
H10 | −0.1301 | −0.1526 | 0.4781 | 0.063* | |
C11 | −0.3324 (3) | −0.19860 (8) | 0.4172 (3) | 0.0655 (5) | |
H11 | −0.3191 | −0.2111 | 0.3219 | 0.079* | |
C12 | −0.4640 (3) | −0.21471 (7) | 0.4657 (3) | 0.0689 (6) | |
H12 | −0.5382 | −0.2388 | 0.4050 | 0.083* | |
C13 | −0.4863 (3) | −0.19547 (8) | 0.6032 (3) | 0.0708 (6) | |
H13 | −0.5781 | −0.2058 | 0.6334 | 0.085* | |
C14 | −0.3720 (3) | −0.16037 (7) | 0.6985 (3) | 0.0563 (4) | |
H14 | −0.3868 | −0.1476 | 0.7928 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.01799 (12) | 0.03007 (15) | 0.02214 (13) | 0.00091 (9) | 0.00756 (9) | 0.00035 (10) |
P2 | 0.01780 (12) | 0.03298 (16) | 0.02239 (13) | 0.00009 (9) | 0.00736 (9) | −0.00164 (10) |
O1 | 0.0328 (4) | 0.0354 (5) | 0.0301 (4) | 0.0006 (4) | 0.0051 (3) | −0.0056 (3) |
O2 | 0.0255 (4) | 0.0393 (5) | 0.0350 (4) | 0.0009 (3) | 0.0167 (3) | 0.0055 (4) |
O3 | 0.0284 (4) | 0.0423 (5) | 0.0243 (4) | 0.0000 (3) | 0.0073 (3) | 0.0042 (3) |
O4 | 0.0219 (4) | 0.0333 (5) | 0.0454 (5) | −0.0004 (3) | 0.0159 (3) | −0.0050 (4) |
O5 | 0.0276 (4) | 0.0650 (7) | 0.0250 (4) | −0.0070 (4) | 0.0076 (3) | −0.0027 (4) |
O6 | 0.0191 (3) | 0.0444 (5) | 0.0345 (4) | 0.0029 (3) | 0.0089 (3) | −0.0056 (4) |
O7 | 0.0382 (5) | 0.0374 (5) | 0.0379 (5) | −0.0049 (4) | 0.0187 (4) | 0.0000 (4) |
N1 | 0.0269 (4) | 0.0310 (5) | 0.0351 (5) | −0.0003 (4) | 0.0143 (4) | −0.0008 (4) |
N2 | 0.0294 (5) | 0.0337 (6) | 0.0367 (5) | −0.0035 (4) | 0.0174 (4) | −0.0033 (4) |
C1 | 0.0359 (6) | 0.0401 (7) | 0.0359 (6) | 0.0054 (5) | 0.0109 (5) | 0.0047 (5) |
C2 | 0.0370 (6) | 0.0323 (6) | 0.0423 (7) | 0.0083 (5) | 0.0158 (5) | 0.0087 (5) |
C3 | 0.0575 (9) | 0.0460 (9) | 0.0719 (11) | 0.0067 (7) | 0.0387 (9) | 0.0124 (8) |
C4 | 0.0679 (13) | 0.0560 (13) | 0.132 (2) | −0.0072 (10) | 0.0504 (15) | 0.0200 (14) |
C5 | 0.0729 (14) | 0.0381 (10) | 0.127 (2) | −0.0086 (10) | 0.0175 (15) | 0.0029 (12) |
C6 | 0.0788 (14) | 0.0419 (10) | 0.0772 (14) | 0.0134 (9) | 0.0128 (11) | −0.0112 (9) |
C7 | 0.0545 (9) | 0.0426 (8) | 0.0528 (9) | 0.0113 (7) | 0.0217 (7) | 0.0000 (7) |
C8 | 0.0315 (6) | 0.0387 (7) | 0.0395 (6) | −0.0033 (5) | 0.0093 (5) | 0.0023 (5) |
C9 | 0.0324 (6) | 0.0309 (6) | 0.0426 (7) | −0.0009 (5) | 0.0106 (5) | 0.0053 (5) |
C10 | 0.0475 (8) | 0.0508 (9) | 0.0612 (10) | −0.0059 (7) | 0.0247 (8) | −0.0099 (8) |
C11 | 0.0687 (12) | 0.0545 (11) | 0.0703 (12) | −0.0080 (9) | 0.0244 (10) | −0.0220 (9) |
C12 | 0.0640 (12) | 0.0480 (10) | 0.0782 (14) | −0.0195 (9) | 0.0110 (10) | −0.0093 (10) |
C13 | 0.0656 (12) | 0.0685 (13) | 0.0795 (14) | −0.0334 (10) | 0.0301 (11) | −0.0005 (11) |
C14 | 0.0568 (10) | 0.0588 (11) | 0.0584 (10) | −0.0203 (8) | 0.0283 (8) | −0.0006 (8) |
P1—O2 | 1.4869 (9) | C3—C4 | 1.396 (3) |
P1—O3 | 1.4953 (9) | C3—H3 | 0.9300 |
P1—O1 | 1.5693 (9) | C4—C5 | 1.353 (4) |
P1—O4 | 1.6042 (9) | C4—H4 | 0.9300 |
P2—O7 | 1.4762 (10) | C5—C6 | 1.369 (4) |
P2—O6 | 1.4987 (9) | C5—H5 | 0.9300 |
P2—O5 | 1.5607 (10) | C6—C7 | 1.388 (3) |
P2—O4 | 1.6166 (10) | C6—H6 | 0.9300 |
O1—H1O1 | 0.8200 | C7—H7 | 0.9300 |
O5—H5O5 | 0.8200 | C8—C9 | 1.5035 (19) |
N1—C1 | 1.4917 (17) | C8—H8A | 0.9700 |
N1—H1N1 | 0.8900 | C8—H8B | 0.9700 |
N1—H2N1 | 0.8900 | C9—C10 | 1.376 (2) |
N1—H3N1 | 0.8900 | C9—C14 | 1.378 (2) |
N2—C8 | 1.4914 (18) | C10—C11 | 1.388 (3) |
N2—H1N2 | 0.8900 | C10—H10 | 0.9300 |
N2—H2N2 | 0.8900 | C11—C12 | 1.372 (3) |
N2—H3N2 | 0.8900 | C11—H11 | 0.9300 |
C1—C2 | 1.504 (2) | C12—C13 | 1.366 (3) |
C1—H1A | 0.9700 | C12—H12 | 0.9300 |
C1—H1B | 0.9700 | C13—C14 | 1.396 (3) |
C2—C3 | 1.382 (2) | C13—H13 | 0.9300 |
C2—C7 | 1.383 (2) | C14—H14 | 0.9300 |
O2—P1—O3 | 116.03 (5) | C4—C3—H3 | 120.1 |
O2—P1—O1 | 112.01 (6) | C5—C4—C3 | 120.6 (2) |
O3—P1—O1 | 108.73 (5) | C5—C4—H4 | 119.7 |
O2—P1—O4 | 110.57 (5) | C3—C4—H4 | 119.7 |
O3—P1—O4 | 108.51 (5) | C4—C5—C6 | 120.2 (2) |
O1—P1—O4 | 99.70 (5) | C4—C5—H5 | 119.9 |
O7—P2—O6 | 118.50 (6) | C6—C5—H5 | 119.9 |
O7—P2—O5 | 112.56 (6) | C5—C6—C7 | 120.3 (2) |
O6—P2—O5 | 108.61 (5) | C5—C6—H6 | 119.9 |
O7—P2—O4 | 109.12 (5) | C7—C6—H6 | 119.9 |
O6—P2—O4 | 102.49 (5) | C2—C7—C6 | 119.97 (19) |
O5—P2—O4 | 104.16 (6) | C2—C7—H7 | 120.0 |
P1—O1—H1O1 | 109.5 | C6—C7—H7 | 120.0 |
P1—O4—P2 | 133.33 (6) | N2—C8—C9 | 111.74 (11) |
P2—O5—H5O5 | 109.5 | N2—C8—H8A | 109.3 |
C1—N1—H1N1 | 109.5 | C9—C8—H8A | 109.3 |
C1—N1—H2N1 | 109.5 | N2—C8—H8B | 109.3 |
H1N1—N1—H2N1 | 109.5 | C9—C8—H8B | 109.3 |
C1—N1—H3N1 | 109.5 | H8A—C8—H8B | 107.9 |
H1N1—N1—H3N1 | 109.5 | C10—C9—C14 | 119.20 (15) |
H2N1—N1—H3N1 | 109.5 | C10—C9—C8 | 119.97 (14) |
C8—N2—H1N2 | 109.5 | C14—C9—C8 | 120.83 (15) |
C8—N2—H2N2 | 109.5 | C9—C10—C11 | 120.81 (18) |
H1N2—N2—H2N2 | 109.5 | C9—C10—H10 | 119.6 |
C8—N2—H3N2 | 109.5 | C11—C10—H10 | 119.6 |
H1N2—N2—H3N2 | 109.5 | C12—C11—C10 | 119.7 (2) |
H2N2—N2—H3N2 | 109.5 | C12—C11—H11 | 120.2 |
N1—C1—C2 | 111.18 (11) | C10—C11—H11 | 120.2 |
N1—C1—H1A | 109.4 | C13—C12—C11 | 120.08 (18) |
C2—C1—H1A | 109.4 | C13—C12—H12 | 120.0 |
N1—C1—H1B | 109.4 | C11—C12—H12 | 120.0 |
C2—C1—H1B | 109.4 | C12—C13—C14 | 120.38 (19) |
H1A—C1—H1B | 108.0 | C12—C13—H13 | 119.8 |
C3—C2—C7 | 119.23 (16) | C14—C13—H13 | 119.8 |
C3—C2—C1 | 120.29 (15) | C9—C14—C13 | 119.82 (19) |
C7—C2—C1 | 120.46 (14) | C9—C14—H14 | 120.1 |
C2—C3—C4 | 119.7 (2) | C13—C14—H14 | 120.1 |
C2—C3—H3 | 120.1 | ||
O2—P1—O4—P2 | 44.21 (10) | C3—C2—C7—C6 | 0.7 (2) |
O3—P1—O4—P2 | −84.10 (10) | C1—C2—C7—C6 | 179.28 (15) |
O1—P1—O4—P2 | 162.27 (9) | C5—C6—C7—C2 | −0.2 (3) |
O7—P2—O4—P1 | −51.43 (10) | N2—C8—C9—C10 | 81.81 (18) |
O6—P2—O4—P1 | −177.87 (9) | N2—C8—C9—C14 | −98.38 (17) |
O5—P2—O4—P1 | 68.98 (10) | C14—C9—C10—C11 | −1.4 (3) |
N1—C1—C2—C3 | 90.66 (17) | C8—C9—C10—C11 | 178.43 (17) |
N1—C1—C2—C7 | −87.87 (16) | C9—C10—C11—C12 | 0.1 (3) |
C7—C2—C3—C4 | −0.2 (3) | C10—C11—C12—C13 | 1.7 (4) |
C1—C2—C3—C4 | −178.79 (18) | C11—C12—C13—C14 | −2.0 (4) |
C2—C3—C4—C5 | −0.8 (4) | C10—C9—C14—C13 | 1.0 (3) |
C3—C4—C5—C6 | 1.3 (4) | C8—C9—C14—C13 | −178.81 (18) |
C4—C5—C6—C7 | −0.8 (4) | C12—C13—C14—C9 | 0.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O6i | 0.82 | 1.90 | 2.7208 (13) | 174 |
O5—H5O5···O3ii | 0.82 | 1.83 | 2.6061 (13) | 158 |
N1—H1N1···O2 | 0.89 | 2.07 | 2.9292 (13) | 162 |
N1—H2N1···O6iii | 0.89 | 2.10 | 2.9698 (15) | 166 |
N1—H2N1···O4iii | 0.89 | 2.53 | 3.1493 (13) | 127 |
N1—H3N1···O7iv | 0.89 | 1.88 | 2.7645 (15) | 169 |
N2—H1N2···O3ii | 0.89 | 1.94 | 2.7956 (15) | 160 |
N2—H2N2···O2 | 0.89 | 1.98 | 2.8637 (15) | 169 |
N2—H3N2···O6iii | 0.89 | 1.99 | 2.8053 (14) | 152 |
C1—H1B···O5ii | 0.97 | 2.52 | 3.3333 (19) | 141 |
C8—H8B···O7 | 0.97 | 2.40 | 3.1558 (17) | 135 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+1; (iii) x−1, y, z; (iv) −x, −y, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O6i | 0.82 | 1.90 | 2.7208 (13) | 174.1 |
O5—H5O5···O3ii | 0.82 | 1.83 | 2.6061 (13) | 158.0 |
N1—H1N1···O2 | 0.89 | 2.07 | 2.9292 (13) | 161.8 |
N1—H2N1···O6iii | 0.89 | 2.10 | 2.9698 (15) | 166.3 |
N1—H2N1···O4iii | 0.89 | 2.53 | 3.1493 (13) | 126.9 |
N1—H3N1···O7iv | 0.89 | 1.88 | 2.7645 (15) | 169.4 |
N2—H1N2···O3ii | 0.89 | 1.94 | 2.7956 (15) | 159.7 |
N2—H2N2···O2 | 0.89 | 1.98 | 2.8637 (15) | 169.3 |
N2—H3N2···O6iii | 0.89 | 1.99 | 2.8053 (14) | 152.0 |
C1—H1B···O5ii | 0.97 | 2.52 | 3.3333 (19) | 140.8 |
C8—H8B···O7 | 0.97 | 2.40 | 3.1558 (17) | 134.8 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+1; (iii) x−1, y, z; (iv) −x, −y, −z+2. |
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
There is current interest in the chemistry of diphosphate materials. They are involved in a variety of bioenergetic (Ernester, 1992; Lipscomb & Strater, 1996) and catalytic processes (Centi et al., 1988; Chen et al., 2002; Ballarini et al., 2006). Considering their relevance in several application areas, we are interested in this type of anion in building new hybrid materials associated to organic cations. We report here, the synthesis and the crystal structure of the title compound (I).
The asymmetric unit of (I) shown in Fig. 1, contains one diphosphate [H2P2O7]2- anion and two crystallographically independent benzylammonium cations. The two PO4 tetrahedral groups are bridged via the O4 bridging oxygen atom with P1—O4—P2 = 133.33 (6)° so as to form the diphosphate anion with a bent configurtation. The conformation is eclipsed evidenced by the psuedo-torsion angle O3—P1···P2—O7 = -6.9°. In the diphosphate group, the longest P—O distances correspond to the bridging oxygen atom with average value d(P—O4) = 1.6104 (8) Å, the intermediate distances are the P—OH bonding [d(P1—O1) = 1.5693 (9) Å, d(P2—O5) = 1.5607 (10) Å], whereas the shortest distances, ranging between 1.4762 (9) Å and 1.4987 (8) Å are related to the terminal oxygen atoms. The average value of the O—P—O angles is 109.25 (5)°. These geometrical features are in same magnitude as observed for diphosphate groups (Akriche et al., 2005; Ahmed et al., 2006; Akriche et al., 2008; Elboulali et al., 2013).
In the crystal, O—H···O and N—H···O hydrogen bonds link the cations and anions forming a two-dimensional network parallel to (010) (Table 1 and Fig. 2). Within this network, weak C—H···O hydrogen bonds are observed (Desiraju, 1991; Steiner 2002).