1-Ammonio-1-phosphono-pentane-1-phospho-nic acid.

The title compound, C(5)H(15)NO(6)P(2), was obtained by the reaction of penta-nenitrile with PCl(3) followed by the dropwise addition of water. The asymmetric unit contains one mol-ecule, which exists as a zwitterion with a positive charge on the -NH(3) group and a negative charge on one of the phospho-nic O atoms. The crystal structure displays N-H⋯O and O-H⋯O hydrogen bonding, which creates a three-dimensional network.

Related literature

For the biological activity of organic disphospho­nic acids, see: Matczak-Jon & Videnova-Adrabinska (2005 ▶); Szabo et al. (2002 ▶); Tromelin et al. (1986 ▶). For comparable bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C5H15NO6P2

M = 247.12

Monoclinic,

a = 14.5502 (3) Å

b = 7.1896 (1) Å

c = 9.4855 (2) Å

β = 96.938 (1)°

V = 985.01 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 100 (2) K

0.38 × 0.36 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.848, T max = 0.961

23409 measured reflections

2471 independent reflections

2225 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.072

S = 1.06

2471 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038968/ez2151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038968/ez2151Isup2.hkl

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

C5H15NO6P2	F000 = 520
Mr = 247.12	Dx = 1.666 Mg m−3
Monoclinic, P21/c	Melting point: 562 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 14.5502 (3) Å	Cell parameters from 8806 reflections
b = 7.1896 (1) Å	θ = 2.8–28.4º
c = 9.4855 (2) Å	µ = 0.45 mm−1
β = 96.938 (1)º	T = 100 (2) K
V = 985.01 (3) Å3	Plate, colourless
Z = 4	0.38 × 0.36 × 0.09 mm

Bruker SMART APEXII CCD area-detector diffractometer	2471 independent reflections
Radiation source: fine-focus sealed tube	2225 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.043
T = 100(2) K	θmax = 28.4º
φ and ω scans	θmin = 2.8º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −19→19
Tmin = 0.848, Tmax = 0.961	k = −9→9
23409 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.072	w = 1/[σ2(Fo2) + (0.0317P)2 + 0.8863P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2471 reflections	Δρmax = 0.44 e Å−3
152 parameters	Δρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.39648 (2)	0.07886 (5)	0.68586 (4)	0.00647 (9)
P2	0.28775 (2)	−0.24846 (5)	0.54892 (4)	0.00680 (9)
C1	0.30732 (9)	0.00397 (19)	0.54146 (14)	0.0067 (3)
C2	0.21901 (10)	0.1205 (2)	0.55184 (15)	0.0100 (3)
H2A	0.1914	0.0778	0.6366	0.012*
H2B	0.2383	0.2514	0.5692	0.012*
C3	0.14290 (10)	0.1183 (2)	0.42611 (16)	0.0139 (3)
H3A	0.1698	0.1489	0.3380	0.017*
H3B	0.1157	−0.0079	0.4153	0.017*
C4	0.06761 (12)	0.2576 (3)	0.4478 (2)	0.0239 (4)
H4A	0.0485	0.2381	0.5434	0.029*
H4B	0.0939	0.3844	0.4457	0.029*
C5	−0.01700 (12)	0.2475 (3)	0.3401 (2)	0.0238 (4)
H5A	0.0005	0.2714	0.2452	0.036*
H5B	−0.0620	0.3411	0.3624	0.036*
H5C	−0.0447	0.1234	0.3424	0.036*
N1	0.34540 (9)	0.04748 (18)	0.40433 (12)	0.0075 (2)
O1	0.20552 (7)	−0.29755 (15)	0.43309 (11)	0.0103 (2)
O2	0.26347 (7)	−0.29945 (15)	0.69151 (10)	0.0105 (2)
O3	0.37688 (7)	−0.33350 (15)	0.50568 (11)	0.0102 (2)
O4	0.48097 (7)	−0.03933 (15)	0.68442 (11)	0.0106 (2)
O5	0.35286 (7)	0.08211 (14)	0.82242 (10)	0.0092 (2)
O6	0.41170 (7)	0.28091 (15)	0.63361 (11)	0.0103 (2)
H1N	0.4006 (14)	0.015 (3)	0.406 (2)	0.015 (5)*
H2N	0.3439 (14)	0.172 (3)	0.387 (2)	0.022 (5)*
H3N	0.3141 (13)	−0.009 (3)	0.331 (2)	0.014 (5)*
H1O	0.2192 (17)	−0.283 (4)	0.356 (3)	0.032 (6)*
H3O	0.3713 (18)	−0.416 (4)	0.450 (3)	0.040 (7)*
H6O	0.4518 (18)	0.340 (4)	0.684 (3)	0.046 (8)*

	U11	U22	U33	U12	U13	U23
P1	0.00764 (16)	0.00625 (17)	0.00532 (16)	−0.00016 (12)	−0.00004 (12)	−0.00001 (12)
P2	0.00865 (17)	0.00661 (17)	0.00509 (16)	−0.00071 (12)	0.00064 (12)	−0.00014 (12)
C1	0.0075 (6)	0.0081 (6)	0.0045 (6)	0.0003 (5)	0.0007 (5)	0.0000 (5)
C2	0.0085 (6)	0.0107 (7)	0.0107 (6)	0.0022 (5)	0.0010 (5)	−0.0017 (5)
C3	0.0119 (7)	0.0176 (8)	0.0114 (7)	0.0050 (6)	−0.0014 (5)	−0.0005 (6)
C4	0.0146 (8)	0.0292 (10)	0.0264 (9)	0.0094 (7)	−0.0043 (7)	−0.0081 (7)
C5	0.0140 (7)	0.0316 (10)	0.0249 (9)	0.0078 (7)	−0.0024 (6)	0.0026 (7)
N1	0.0082 (6)	0.0087 (6)	0.0058 (5)	−0.0007 (4)	0.0011 (4)	−0.0002 (4)
O1	0.0113 (5)	0.0123 (5)	0.0070 (5)	−0.0025 (4)	0.0002 (4)	−0.0008 (4)
O2	0.0142 (5)	0.0105 (5)	0.0068 (4)	−0.0006 (4)	0.0018 (4)	0.0006 (4)
O3	0.0116 (5)	0.0083 (5)	0.0109 (5)	0.0009 (4)	0.0022 (4)	−0.0026 (4)
O4	0.0095 (5)	0.0122 (5)	0.0096 (5)	0.0026 (4)	−0.0004 (4)	−0.0001 (4)
O5	0.0123 (5)	0.0087 (5)	0.0067 (4)	−0.0001 (4)	0.0016 (4)	−0.0003 (4)
O6	0.0134 (5)	0.0079 (5)	0.0089 (5)	−0.0031 (4)	−0.0007 (4)	0.0013 (4)

P1—O4	1.4959 (10)	C3—H3A	0.9900
P1—O5	1.5099 (10)	C3—H3B	0.9900
P1—O6	1.5593 (11)	C4—C5	1.504 (2)
P1—C1	1.8492 (14)	C4—H4A	0.9900
P2—O2	1.4846 (10)	C4—H4B	0.9900
P2—O3	1.5337 (11)	C5—H5A	0.9800
P2—O1	1.5639 (10)	C5—H5B	0.9800
P2—C1	1.8398 (14)	C5—H5C	0.9800
C1—N1	1.5070 (17)	N1—H1N	0.84 (2)
C1—C2	1.5471 (19)	N1—H2N	0.91 (2)
C2—C3	1.5264 (19)	N1—H3N	0.88 (2)
C2—H2A	0.9900	O1—H1O	0.79 (2)
C2—H2B	0.9900	O3—H3O	0.79 (3)
C3—C4	1.517 (2)	O6—H6O	0.83 (3)
O4—P1—O5	116.59 (6)	C2—C3—H3A	109.5
O4—P1—O6	112.20 (6)	C4—C3—H3B	109.5
O5—P1—O6	110.42 (6)	C2—C3—H3B	109.5
O4—P1—C1	109.37 (6)	H3A—C3—H3B	108.1
O5—P1—C1	108.06 (6)	C5—C4—C3	114.90 (15)
O6—P1—C1	98.61 (6)	C5—C4—H4A	108.5
O2—P2—O3	116.57 (6)	C3—C4—H4A	108.5
O2—P2—O1	109.77 (6)	C5—C4—H4B	108.5
O3—P2—O1	108.78 (6)	C3—C4—H4B	108.5
O2—P2—C1	109.49 (6)	H4A—C4—H4B	107.5
O3—P2—C1	104.08 (6)	C4—C5—H5A	109.5
O1—P2—C1	107.72 (6)	C4—C5—H5B	109.5
N1—C1—C2	109.71 (11)	H5A—C5—H5B	109.5
N1—C1—P2	108.22 (9)	C4—C5—H5C	109.5
C2—C1—P2	113.48 (10)	H5A—C5—H5C	109.5
N1—C1—P1	106.30 (9)	H5B—C5—H5C	109.5
C2—C1—P1	107.99 (9)	C1—N1—H1N	112.5 (13)
P2—C1—P1	110.90 (7)	C1—N1—H2N	111.0 (13)
C3—C2—C1	118.31 (12)	H1N—N1—H2N	106.4 (19)
C3—C2—H2A	107.7	C1—N1—H3N	112.3 (12)
C1—C2—H2A	107.7	H1N—N1—H3N	106.5 (18)
C3—C2—H2B	107.7	H2N—N1—H3N	107.9 (18)
C1—C2—H2B	107.7	P2—O1—H1O	111.4 (17)
H2A—C2—H2B	107.1	P2—O3—H3O	117.1 (19)
C4—C3—C2	110.76 (13)	P1—O6—H6O	114.5 (19)
C4—C3—H3A	109.5
O2—P2—C1—N1	171.72 (8)	O4—P1—C1—C2	176.54 (9)
O3—P2—C1—N1	46.42 (10)	O5—P1—C1—C2	48.68 (11)
O1—P2—C1—N1	−68.96 (10)	O6—P1—C1—C2	−66.19 (10)
O2—P2—C1—C2	−66.27 (11)	O4—P1—C1—P2	51.62 (9)
O3—P2—C1—C2	168.44 (9)	O5—P1—C1—P2	−76.24 (8)
O1—P2—C1—C2	53.05 (11)	O6—P1—C1—P2	168.90 (7)
O2—P2—C1—P1	55.49 (9)	N1—C1—C2—C3	50.75 (17)
O3—P2—C1—P1	−69.81 (8)	P2—C1—C2—C3	−70.43 (15)
O1—P2—C1—P1	174.81 (7)	P1—C1—C2—C3	166.21 (11)
O4—P1—C1—N1	−65.79 (10)	C1—C2—C3—C4	−173.11 (14)
O5—P1—C1—N1	166.35 (9)	C2—C3—C4—C5	−171.76 (15)
O6—P1—C1—N1	51.49 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4i	0.84 (2)	2.02 (2)	2.7584 (16)	146.7 (19)
N1—H2N···O5ii	0.91 (2)	1.88 (2)	2.7799 (16)	169.4 (19)
N1—H3N···O2iii	0.88 (2)	1.99 (2)	2.8451 (16)	162.9 (18)
O1—H1O···O2iii	0.79 (2)	1.85 (3)	2.6297 (15)	167 (3)
O3—H3O···O5iii	0.79 (3)	1.70 (3)	2.4884 (15)	175 (3)
O6—H6O···O4iv	0.83 (3)	1.72 (3)	2.5372 (14)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4i	0.84 (2)	2.02 (2)	2.7584 (16)	146.7 (19)
N1—H2N⋯O5ii	0.91 (2)	1.88 (2)	2.7799 (16)	169.4 (19)
N1—H3N⋯O2iii	0.88 (2)	1.99 (2)	2.8451 (16)	162.9 (18)
O1—H1O⋯O2iii	0.79 (2)	1.85 (3)	2.6297 (15)	167 (3)
O3—H3O⋯O5iii	0.79 (3)	1.70 (3)	2.4884 (15)	175 (3)
O6—H6O⋯O4iv	0.83 (3)	1.72 (3)	2.5372 (14)	168 (3)

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