Bis(4-meth-oxy-benzyl-ammonium) dihydrogen diphosphate.

In the title compound, 2C(8)H(12)NO(+)·H(2)P(2)O(7) (2-), the linked PO(4) groups of the diphosphate anion are almost eclipsed and the P-O-P angle is 134.45 (7)°. In the crystal, infinite ribbons of H(2)P(2)O(7) (2-) anions propagate in [100], being linked by strong O-H⋯O hydrogen bonds. The 4-meth-oxy-benzyl-ammonium cations bond to the diphosphate chains by N-H⋯O and C-H⋯O links, and are themselves linked by C-H⋯π inter-actions.

Related literature

For background to diphosphates, see: Ballarini et al. (2006 ▶); For inter­molecular inter­actions, see: Brown (1976 ▶); Tiekink & Zukerman-Schpector (2012 ▶). For a related structure, see: Ahmed et al. (2006 ▶).

Experimental

Crystal data

2C8H12NO+·H2P2O7 2−

M = 452.33

Triclinic,

a = 9.184 (3) Å

b = 6.737 (4) Å

c = 17.066 (2) Å

α = 97.61 (2)°

β = 91.39 (4)°

γ = 85.72 (3)°

V = 1043.6 (7) Å3

Z = 2

Ag Kα radiation

λ = 0.56087 Å

μ = 0.14 mm−1

T = 296 K

0.30 × 0.25 × 0.17 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

12631 measured reflections

10225 independent reflections

5553 reflections with I > 2σ(I)

R int = 0.026

2 standard reflections every 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.143

S = 0.98

10225 reflections

268 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.51 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051616/hb7003sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051616/hb7003Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051616/hb7003Isup3.cml

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

2C8H12NO+·H2O7P22−	Z = 2
Mr = 452.33	F(000) = 476
Triclinic, P1	Dx = 1.439 Mg m−3
a = 9.184 (3) Å	Ag Kα radiation, λ = 0.56087 Å
b = 6.737 (4) Å	Cell parameters from 25 reflections
c = 17.066 (2) Å	θ = 9–11°
α = 97.61 (2)°	µ = 0.14 mm−1
β = 91.39 (4)°	T = 296 K
γ = 85.72 (3)°	Prism, colorless
V = 1043.6 (7) Å3	0.30 × 0.25 × 0.17 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.026
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.0°
Graphite monochromator	h = −15→15
non–profiled ω scans	k = −11→11
12631 measured reflections	l = −4→28
10225 independent reflections	2 standard reflections every 120 min
5553 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0674P)2] where P = (Fo2 + 2Fc2)/3
10225 reflections	(Δ/σ)max = 0.001
268 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.51 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.

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.

	x	y	z	Uiso*/Ueq
P1	0.77375 (4)	−0.16843 (5)	0.42717 (2)	0.02283 (9)
P2	0.71445 (4)	0.14070 (5)	0.56549 (2)	0.02389 (9)
O1	0.65658 (11)	−0.21336 (18)	0.36026 (7)	0.0321 (2)
H1	0.5815	−0.2428	0.3796	0.048*
O2	0.90518 (11)	−0.09884 (18)	0.39193 (7)	0.0347 (3)
O3	0.80044 (12)	−0.33687 (15)	0.47500 (7)	0.0309 (2)
O4	0.69102 (12)	0.02214 (16)	0.47816 (7)	0.0327 (3)
O5	0.85320 (11)	0.25556 (17)	0.55945 (8)	0.0361 (3)
H5	0.9218	0.2006	0.5819	0.054*
O6	0.58394 (11)	0.29007 (16)	0.57185 (7)	0.0341 (3)
O7	0.73241 (13)	−0.00463 (17)	0.62306 (7)	0.0359 (3)
O8	0.65303 (18)	0.1234 (3)	0.06727 (9)	0.0624 (4)
O9	0.14301 (19)	0.4144 (3)	0.07212 (10)	0.0663 (5)
N1	0.98380 (14)	0.31496 (19)	0.40133 (8)	0.0301 (3)
H1A	0.9110	0.4056	0.4165	0.045*
H1B	1.0568	0.3266	0.4365	0.045*
H1C	0.9523	0.1923	0.3980	0.045*
N2	0.45655 (14)	0.30089 (19)	0.39890 (8)	0.0323 (3)
H2A	0.4183	0.4264	0.4106	0.048*
H2B	0.5181	0.2707	0.4374	0.048*
H2C	0.3854	0.2171	0.3941	0.048*
C1	1.03636 (18)	0.3492 (3)	0.32239 (10)	0.0365 (4)
H1D	1.1277	0.2697	0.3113	0.044*
H1E	1.0554	0.4895	0.3242	0.044*
C2	0.92910 (18)	0.2956 (3)	0.25659 (10)	0.0327 (3)
C3	0.8548 (2)	0.4405 (3)	0.21786 (12)	0.0419 (4)
H3	0.8676	0.5751	0.2348	0.050*
C4	0.7619 (2)	0.3905 (3)	0.15447 (12)	0.0473 (5)
H4	0.7144	0.4906	0.1286	0.057*
C5	0.7401 (2)	0.1919 (3)	0.12986 (11)	0.0443 (4)
C6	0.8102 (3)	0.0456 (3)	0.16945 (12)	0.0507 (5)
H6	0.7930	−0.0885	0.1543	0.061*
C7	0.9056 (2)	0.0964 (3)	0.23126 (11)	0.0447 (4)
H7	0.9548	−0.0041	0.2562	0.054*
C8	0.5843 (3)	0.2674 (5)	0.02229 (15)	0.0744 (8)
H8A	0.5198	0.3591	0.0555	0.112*
H8B	0.5293	0.2004	−0.0205	0.112*
H8C	0.6572	0.3402	0.0015	0.112*
C9	0.53647 (18)	0.2817 (3)	0.32319 (11)	0.0395 (4)
H9A	0.5868	0.1492	0.3133	0.047*
H9B	0.6091	0.3801	0.3271	0.047*
C10	0.43368 (18)	0.3132 (3)	0.25591 (11)	0.0360 (4)
C11	0.3878 (2)	0.5050 (3)	0.23911 (12)	0.0465 (5)
H11	0.4236	0.6163	0.2695	0.056*
C12	0.2903 (3)	0.5326 (3)	0.17823 (13)	0.0526 (5)
H12	0.2606	0.6620	0.1682	0.063*
C13	0.2364 (2)	0.3700 (3)	0.13206 (12)	0.0455 (4)
C14	0.2793 (2)	0.1798 (3)	0.14782 (12)	0.0491 (5)
H14	0.2433	0.0692	0.1171	0.059*
C15	0.3766 (2)	0.1526 (3)	0.20981 (12)	0.0445 (4)
H15	0.4038	0.0231	0.2205	0.053*
C16	0.0827 (3)	0.2508 (4)	0.02453 (16)	0.0760 (8)
H16A	0.1601	0.1615	0.0004	0.114*
H16B	0.0210	0.3002	−0.0159	0.114*
H16C	0.0263	0.1799	0.0569	0.114*

	U11	U22	U33	U12	U13	U23
P1	0.01629 (14)	0.02364 (17)	0.0285 (2)	−0.00016 (12)	−0.00173 (13)	0.00439 (14)
P2	0.01804 (15)	0.02244 (16)	0.0311 (2)	−0.00183 (12)	−0.00096 (14)	0.00320 (14)
O1	0.0211 (5)	0.0425 (6)	0.0319 (6)	−0.0046 (4)	−0.0042 (4)	0.0013 (5)
O2	0.0191 (4)	0.0422 (6)	0.0458 (7)	−0.0045 (4)	0.0003 (5)	0.0157 (5)
O3	0.0299 (5)	0.0262 (5)	0.0373 (7)	0.0021 (4)	−0.0002 (5)	0.0096 (5)
O4	0.0319 (5)	0.0297 (5)	0.0337 (6)	0.0072 (4)	−0.0070 (5)	−0.0003 (5)
O5	0.0195 (5)	0.0337 (6)	0.0582 (8)	−0.0066 (4)	−0.0068 (5)	0.0160 (5)
O6	0.0200 (4)	0.0297 (5)	0.0504 (8)	0.0015 (4)	0.0020 (5)	−0.0009 (5)
O7	0.0371 (6)	0.0362 (6)	0.0371 (7)	−0.0085 (5)	−0.0051 (5)	0.0124 (5)
O8	0.0640 (10)	0.0773 (11)	0.0443 (9)	−0.0109 (8)	−0.0196 (8)	0.0029 (8)
O9	0.0745 (11)	0.0750 (11)	0.0490 (10)	−0.0068 (9)	−0.0228 (8)	0.0100 (8)
N1	0.0280 (6)	0.0303 (6)	0.0313 (7)	0.0010 (5)	−0.0034 (5)	0.0038 (5)
N2	0.0325 (6)	0.0291 (6)	0.0364 (8)	−0.0037 (5)	−0.0072 (6)	0.0090 (6)
C1	0.0319 (8)	0.0474 (9)	0.0313 (9)	−0.0057 (7)	0.0016 (7)	0.0071 (7)
C2	0.0343 (8)	0.0377 (8)	0.0265 (8)	−0.0014 (6)	0.0024 (6)	0.0059 (7)
C3	0.0450 (10)	0.0372 (9)	0.0432 (11)	0.0004 (7)	−0.0025 (8)	0.0070 (8)
C4	0.0459 (10)	0.0512 (11)	0.0445 (12)	0.0066 (8)	−0.0079 (9)	0.0121 (9)
C5	0.0417 (9)	0.0587 (12)	0.0319 (10)	−0.0050 (8)	−0.0020 (8)	0.0037 (9)
C6	0.0744 (14)	0.0412 (10)	0.0369 (11)	−0.0123 (9)	−0.0061 (10)	0.0036 (8)
C7	0.0614 (12)	0.0396 (9)	0.0331 (10)	0.0004 (8)	−0.0048 (9)	0.0085 (8)
C8	0.0625 (15)	0.109 (2)	0.0515 (15)	−0.0036 (14)	−0.0244 (12)	0.0165 (15)
C9	0.0296 (7)	0.0436 (9)	0.0453 (11)	0.0017 (7)	0.0023 (7)	0.0077 (8)
C10	0.0348 (8)	0.0395 (8)	0.0341 (9)	−0.0020 (7)	0.0033 (7)	0.0067 (7)
C11	0.0615 (12)	0.0386 (9)	0.0396 (11)	−0.0078 (8)	−0.0079 (9)	0.0058 (8)
C12	0.0701 (14)	0.0441 (10)	0.0449 (12)	−0.0030 (10)	−0.0107 (10)	0.0126 (9)
C13	0.0470 (10)	0.0570 (11)	0.0328 (10)	−0.0039 (9)	−0.0013 (8)	0.0074 (9)
C14	0.0541 (11)	0.0489 (11)	0.0431 (12)	−0.0122 (9)	−0.0006 (9)	−0.0028 (9)
C15	0.0494 (10)	0.0379 (9)	0.0459 (12)	−0.0026 (8)	0.0020 (9)	0.0043 (8)
C16	0.0716 (17)	0.095 (2)	0.0559 (16)	−0.0066 (15)	−0.0233 (13)	−0.0054 (14)

P1—O3	1.4860 (13)	C3—C4	1.383 (3)
P1—O2	1.4942 (12)	C3—H3	0.9300
P1—O1	1.5656 (13)	C4—C5	1.376 (3)
P1—O4	1.6042 (13)	C4—H4	0.9300
P2—O7	1.4744 (13)	C5—C6	1.380 (3)
P2—O6	1.5028 (12)	C6—C7	1.379 (3)
P2—O5	1.5517 (12)	C6—H6	0.9300
P2—O4	1.6126 (12)	C7—H7	0.9300
O1—H1	0.8200	C8—H8A	0.9600
O5—H5	0.8200	C8—H8B	0.9600
O8—C5	1.370 (2)	C8—H8C	0.9600
O8—C8	1.418 (3)	C9—C10	1.495 (3)
O9—C13	1.368 (2)	C9—H9A	0.9700
O9—C16	1.419 (3)	C9—H9B	0.9700
N1—C1	1.494 (2)	C10—C15	1.380 (3)
N1—H1A	0.8900	C10—C11	1.393 (3)
N1—H1B	0.8900	C11—C12	1.377 (3)
N1—H1C	0.8900	C11—H11	0.9300
N2—C9	1.487 (2)	C12—C13	1.378 (3)
N2—H2A	0.8900	C12—H12	0.9300
N2—H2B	0.8900	C13—C14	1.371 (3)
N2—H2C	0.8900	C14—C15	1.390 (3)
C1—C2	1.501 (2)	C14—H14	0.9300
C1—H1D	0.9700	C15—H15	0.9300
C1—H1E	0.9700	C16—H16A	0.9600
C2—C3	1.380 (2)	C16—H16B	0.9600
C2—C7	1.386 (3)	C16—H16C	0.9600
O3—P1—O2	116.25 (7)	O8—C5—C6	115.48 (19)
O3—P1—O1	112.16 (7)	C4—C5—C6	119.39 (18)
O2—P1—O1	108.81 (7)	C7—C6—C5	120.56 (19)
O3—P1—O4	110.72 (7)	C7—C6—H6	119.7
O2—P1—O4	107.92 (8)	C5—C6—H6	119.7
O1—P1—O4	99.63 (6)	C6—C7—C2	120.72 (18)
O7—P2—O6	118.73 (8)	C6—C7—H7	119.6
O7—P2—O5	112.51 (7)	C2—C7—H7	119.6
O6—P2—O5	108.43 (7)	O8—C8—H8A	109.5
O7—P2—O4	109.41 (7)	O8—C8—H8B	109.5
O6—P2—O4	101.55 (7)	H8A—C8—H8B	109.5
O5—P2—O4	104.81 (8)	O8—C8—H8C	109.5
P1—O1—H1	109.5	H8A—C8—H8C	109.5
P1—O4—P2	134.45 (7)	H8B—C8—H8C	109.5
P2—O5—H5	109.5	N2—C9—C10	110.84 (14)
C5—O8—C8	117.59 (19)	N2—C9—H9A	109.5
C13—O9—C16	117.15 (19)	C10—C9—H9A	109.5
C1—N1—H1A	109.5	N2—C9—H9B	109.5
C1—N1—H1B	109.5	C10—C9—H9B	109.5
H1A—N1—H1B	109.5	H9A—C9—H9B	108.1
C1—N1—H1C	109.5	C15—C10—C11	117.43 (18)
H1A—N1—H1C	109.5	C15—C10—C9	120.98 (17)
H1B—N1—H1C	109.5	C11—C10—C9	121.55 (17)
C9—N2—H2A	109.5	C12—C11—C10	121.12 (18)
C9—N2—H2B	109.5	C12—C11—H11	119.4
H2A—N2—H2B	109.5	C10—C11—H11	119.4
C9—N2—H2C	109.5	C11—C12—C13	120.5 (2)
H2A—N2—H2C	109.5	C11—C12—H12	119.8
H2B—N2—H2C	109.5	C13—C12—H12	119.8
N1—C1—C2	112.96 (14)	O9—C13—C14	124.96 (19)
N1—C1—H1D	109.0	O9—C13—C12	115.6 (2)
C2—C1—H1D	109.0	C14—C13—C12	119.42 (19)
N1—C1—H1E	109.0	C13—C14—C15	119.92 (18)
C2—C1—H1E	109.0	C13—C14—H14	120.0
H1D—C1—H1E	107.8	C15—C14—H14	120.0
C3—C2—C7	117.96 (17)	C10—C15—C14	121.60 (19)
C3—C2—C1	121.67 (16)	C10—C15—H15	119.2
C7—C2—C1	120.33 (16)	C14—C15—H15	119.2
C2—C3—C4	121.69 (18)	O9—C16—H16A	109.5
C2—C3—H3	119.2	O9—C16—H16B	109.5
C4—C3—H3	119.2	H16A—C16—H16B	109.5
C5—C4—C3	119.64 (18)	O9—C16—H16C	109.5
C5—C4—H4	120.2	H16A—C16—H16C	109.5
C3—C4—H4	120.2	H16B—C16—H16C	109.5
O8—C5—C4	125.13 (19)
O3—P1—O4—P2	47.66 (13)	C5—C6—C7—C2	2.2 (3)
O2—P1—O4—P2	−80.60 (12)	C3—C2—C7—C6	−0.3 (3)
O1—P1—O4—P2	165.91 (11)	C1—C2—C7—C6	−178.26 (18)
O7—P2—O4—P1	−48.92 (13)	N2—C9—C10—C15	−94.9 (2)
O6—P2—O4—P1	−175.23 (10)	N2—C9—C10—C11	82.7 (2)
O5—P2—O4—P1	71.95 (12)	C15—C10—C11—C12	−0.7 (3)
N1—C1—C2—C3	110.56 (19)	C9—C10—C11—C12	−178.38 (19)
N1—C1—C2—C7	−71.6 (2)	C10—C11—C12—C13	−0.4 (4)
C7—C2—C3—C4	−1.4 (3)	C16—O9—C13—C14	2.2 (3)
C1—C2—C3—C4	176.49 (18)	C16—O9—C13—C12	−178.6 (2)
C2—C3—C4—C5	1.2 (3)	C11—C12—C13—O9	−178.5 (2)
C8—O8—C5—C4	2.6 (3)	C11—C12—C13—C14	0.8 (3)
C8—O8—C5—C6	−177.0 (2)	O9—C13—C14—C15	179.08 (19)
C3—C4—C5—O8	−178.81 (19)	C12—C13—C14—C15	−0.1 (3)
C3—C4—C5—C6	0.7 (3)	C11—C10—C15—C14	1.3 (3)
O8—C5—C6—C7	177.14 (19)	C9—C10—C15—C14	179.06 (18)
C4—C5—C6—C7	−2.4 (3)	C13—C14—C15—C10	−0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6i	0.82	1.82	2.6347 (18)	176
O5—H5···O2ii	0.82	1.75	2.5535 (18)	164
N1—H1A···O3iii	0.89	2.09	2.941 (2)	160
N1—H1B···O3ii	0.89	1.97	2.857 (2)	172
N1—H1C···O2	0.89	2.03	2.915 (2)	173
N2—H2B···O6	0.89	2.35	3.156 (2)	151
N2—H2A···O6iv	0.89	1.89	2.734 (2)	157
N2—H2B···O4	0.89	2.38	3.150 (2)	145
N2—H2C···O7i	0.89	1.85	2.724 (2)	168
C1—H1D···O7ii	0.97	2.49	3.242 (3)	134
C7—H7···O2	0.93	2.54	3.195 (2)	127
C16—H16C···Cg1v	0.96	2.93	3.73 (7)	142
C8—H8A···Cg2	0.96	2.97	3.72 (7)	137
C1—H1D···Cg2vi	0.97	2.90	3.54 (7)	124

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O6i	0.82	1.82	2.6347 (18)	176
O5—H5⋯O2ii	0.82	1.75	2.5535 (18)	164
N1—H1A⋯O3iii	0.89	2.09	2.941 (2)	160
N1—H1B⋯O3ii	0.89	1.97	2.857 (2)	172
N1—H1C⋯O2	0.89	2.03	2.915 (2)	173
N2—H2B⋯O6	0.89	2.35	3.156 (2)	151
N2—H2A⋯O6iv	0.89	1.89	2.734 (2)	157
N2—H2B⋯O4	0.89	2.38	3.150 (2)	145
N2—H2C⋯O7i	0.89	1.85	2.724 (2)	168
C1—H1D⋯O7ii	0.97	2.49	3.242 (3)	134
C7—H7⋯O2	0.93	2.54	3.195 (2)	127
C16—H16C⋯Cg1v	0.96	2.93	3.73 (7)	142
C8—H8A⋯Cg2	0.96	2.97	3.72 (7)	137
C1—H1D⋯Cg2vi	0.97	2.90	3.54 (7)	124

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .