Bis(benzyl-ammonium) di-hydrogen diphosphate.

The asymmetric unit of the title salt, 2C6H5CH2NH3 (+)·H2P2O7 (2-), contains two independent benzyl-ammonium cations and a di-hydrogen 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.

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

2C7H10N+·H2P2O7 2−

M = 392.27

Monoclinic,

a = 8.1337 (2) Å

b = 28.9015 (9) Å

c = 8.4727 (2) Å

β = 113.449 (1)°

V = 1827.24 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.3 × 0.2 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer

27919 measured reflections

7410 independent reflections

5946 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.127

S = 1.06

7410 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.28 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: 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 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813032455/lh5670sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032455/lh5670Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032455/lh5670Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iii) ; (iv) .