(R)-(1-Ammonio-prop-yl)phospho-nate.

The title compound, C(3)H(10)NO(3)P, crystallizes in its zwitterionic form, H(3)N(+)CH(C(2)H(5))PO(O(-))(OH), with the asymmetric unit being composed by two of such entities (Z' = 2). The crystal packing leads to a sequence of hydro-phobic and hydro-philic layers. While the hydro-phobic layer comprises the aliphatic substituent groups, the hydro-philic one is held together by a series of strong and rather directional N(+)-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For a description of the graph-set notation for hydrogen-bonded aggregates, see: Grell et al. (1999 ▶). For basic stereochemistry terminology, see: Moss (1996 ▶). For the biological activity of the title compound, see: Hudson & Ismail (2001 ▶). For the crystal structure of a racemic mixture containing the title compound, see: Bashall et al. (2010 ▶). For previous work from our research group on the assembly of coordination polymers using phospho­nic-based mol­ecules, see: Cunha-Silva, Ananias et al. (2009 ▶); Cunha-Silva, Lima et al. (2009 ▶); Cunha-Silva et al. (2007 ▶); Rocha et al. (2009 ▶); Shi, Cunha-Silva et al. (2008 ▶); Shi, Trindade et al. (2008 ▶). For a related structure, see: Fernandes et al. (2010 ▶). For a description of the TOPOS software, see: Blatov & Proserpio (2009 ▶).

Experimental

Crystal data

C3H10NO3P

M = 139.09

Monoclinic,

a = 9.3988 (13) Å

b = 6.2511 (8) Å

c = 10.8575 (15) Å

β = 105.731 (9)°

V = 614.02 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 150 K

0.16 × 0.08 × 0.02 mm

Data collection

Bruker X8 Kappa CCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.943, T max = 0.993

23447 measured reflections

4196 independent reflections

3465 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.088

S = 1.06

4196 reflections

171 parameters

15 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.55 e Å−3

Absolute structure: Flack (1983 ▶), 1730 Friedel pairs

Flack parameter: −0.03 (8)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040304/pk2268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040304/pk2268Isup2.hkl

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

C3H10NO3P	F(000) = 296
Mr = 139.09	Dx = 1.505 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6291 reflections
a = 9.3988 (13) Å	θ = 2.3–32.1°
b = 6.2511 (8) Å	µ = 0.37 mm−1
c = 10.8575 (15) Å	T = 150 K
β = 105.731 (9)°	Plate, colourless
V = 614.02 (14) Å3	0.16 × 0.08 × 0.02 mm
Z = 4

Bruker X8 Kappa CCD APEXII diffractometer	4196 independent reflections
Radiation source: fine-focus sealed tube	3465 reflections with I > 2σ(I)
graphite	Rint = 0.053
ω and φ scans	θmax = 33.1°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −14→14
Tmin = 0.943, Tmax = 0.993	k = −7→9
23447 measured reflections	l = −16→16

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0396P)2 + 0.1217P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4196 reflections	Δρmax = 0.38 e Å−3
171 parameters	Δρmin = −0.55 e Å−3
15 restraints	Absolute structure: Flack (1983), 1730 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (8)

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	0.17626 (5)	0.89317 (8)	0.65337 (5)	0.01280 (11)
O1	0.29018 (16)	0.7215 (2)	0.69950 (15)	0.0197 (3)
O2	0.10172 (14)	0.8923 (3)	0.51232 (13)	0.0182 (3)
O3	0.06166 (16)	0.8928 (3)	0.73443 (14)	0.0272 (4)
H3D	−0.0346 (16)	0.837 (4)	0.707 (3)	0.041*
N1	0.1977 (2)	1.3190 (3)	0.60484 (18)	0.0159 (4)
H1	0.231 (2)	1.455 (2)	0.6360 (19)	0.024*
H2	0.0945 (11)	1.307 (4)	0.595 (2)	0.024*
H3	0.217 (2)	1.294 (4)	0.5245 (13)	0.024*
C1	0.2726 (2)	1.1499 (4)	0.69718 (19)	0.0162 (4)
H1A	0.3742	1.1320	0.6863	0.019*
C2	0.2910 (3)	1.2237 (4)	0.8348 (2)	0.0218 (5)
H2A	0.3340	1.3693	0.8453	0.026*
H2B	0.1924	1.2317	0.8509	0.026*
C3	0.3897 (3)	1.0758 (4)	0.9338 (2)	0.0248 (5)
H3A	0.3438	0.9341	0.9287	0.037*
H3B	0.4021	1.1351	1.0196	0.037*
H3C	0.4865	1.0631	0.9167	0.037*
P2	0.64788 (6)	0.66572 (8)	0.65107 (5)	0.01273 (11)
O4	0.78570 (16)	0.7909 (2)	0.65226 (15)	0.0177 (3)
O5	0.54723 (16)	0.6182 (2)	0.52207 (13)	0.0180 (3)
O6	0.57135 (16)	0.7875 (2)	0.74254 (14)	0.0169 (3)
H6A	0.4679 (11)	0.771 (5)	0.725 (2)	0.025*
N2	0.71494 (19)	0.2456 (3)	0.63228 (17)	0.0144 (4)
H4	0.744 (2)	0.109 (2)	0.6697 (19)	0.022*
H5	0.6217 (12)	0.230 (3)	0.5709 (16)	0.022*
H6	0.7853 (16)	0.289 (3)	0.5885 (18)	0.022*
C4	0.6989 (2)	0.4063 (3)	0.72982 (18)	0.0133 (4)
H4A	0.6149	0.3588	0.7634	0.016*
C5	0.8369 (2)	0.4151 (4)	0.8428 (2)	0.0208 (4)
H5A	0.8269	0.5351	0.8994	0.025*
H5B	0.9237	0.4449	0.8103	0.025*
C6	0.8649 (3)	0.2079 (4)	0.9217 (2)	0.0298 (6)
H6B	0.7746	0.1666	0.9443	0.045*
H6C	0.9448	0.2312	0.9999	0.045*
H6D	0.8932	0.0938	0.8711	0.045*

	U11	U22	U33	U12	U13	U23
P1	0.0114 (2)	0.0102 (2)	0.0176 (2)	−0.0005 (2)	0.00522 (17)	−0.0016 (2)
O1	0.0169 (7)	0.0114 (8)	0.0292 (8)	0.0003 (6)	0.0034 (6)	0.0005 (6)
O2	0.0167 (6)	0.0171 (7)	0.0207 (7)	−0.0024 (7)	0.0049 (5)	−0.0027 (7)
O3	0.0165 (7)	0.0427 (10)	0.0238 (8)	−0.0090 (9)	0.0079 (6)	−0.0080 (9)
N1	0.0193 (9)	0.0098 (8)	0.0178 (9)	0.0005 (7)	0.0035 (7)	−0.0007 (7)
C1	0.0172 (9)	0.0099 (9)	0.0200 (10)	0.0010 (8)	0.0025 (7)	0.0007 (8)
C2	0.0295 (12)	0.0170 (11)	0.0175 (10)	−0.0027 (9)	0.0040 (9)	−0.0034 (8)
C3	0.0323 (13)	0.0226 (12)	0.0177 (11)	−0.0008 (10)	0.0037 (9)	−0.0007 (9)
P2	0.0117 (2)	0.0087 (2)	0.0174 (2)	0.0009 (2)	0.00322 (18)	0.0000 (2)
O4	0.0141 (7)	0.0133 (7)	0.0261 (8)	−0.0006 (6)	0.0063 (6)	−0.0003 (6)
O5	0.0214 (8)	0.0124 (8)	0.0173 (7)	0.0038 (6)	0.0002 (6)	−0.0011 (6)
O6	0.0162 (7)	0.0130 (7)	0.0212 (8)	0.0013 (6)	0.0046 (6)	−0.0041 (6)
N2	0.0155 (8)	0.0094 (8)	0.0163 (9)	0.0010 (7)	0.0006 (7)	−0.0016 (7)
C4	0.0142 (8)	0.0090 (9)	0.0164 (8)	0.0006 (8)	0.0034 (7)	−0.0028 (8)
C5	0.0195 (10)	0.0186 (12)	0.0203 (10)	0.0030 (9)	−0.0014 (8)	−0.0004 (10)
C6	0.0359 (13)	0.0264 (14)	0.0217 (11)	0.0088 (10)	−0.0015 (10)	0.0037 (9)

P1—O2	1.5014 (15)	P2—O5	1.4921 (15)
P1—O1	1.5029 (15)	P2—O4	1.5105 (15)
P1—O3	1.5649 (15)	P2—O6	1.5718 (16)
P1—C1	1.841 (2)	P2—C4	1.836 (2)
O3—H3D	0.939 (10)	O6—H6A	0.944 (10)
N1—C1	1.495 (3)	N2—C4	1.496 (3)
N1—H1	0.939 (9)	N2—H4	0.952 (9)
N1—H2	0.950 (9)	N2—H5	0.951 (9)
N1—H3	0.950 (9)	N2—H6	0.953 (9)
C1—C2	1.528 (3)	C4—C5	1.525 (3)
C1—H1A	1.0000	C4—H4A	1.0000
C2—C3	1.527 (3)	C5—C6	1.536 (3)
C2—H2A	0.9900	C5—H5A	0.9900
C2—H2B	0.9900	C5—H5B	0.9900
C3—H3A	0.9800	C6—H6B	0.9800
C3—H3B	0.9800	C6—H6C	0.9800
C3—H3C	0.9800	C6—H6D	0.9800
O2—P1—O1	115.51 (9)	O5—P2—O4	115.80 (9)
O2—P1—O3	111.82 (8)	O5—P2—O6	114.03 (8)
O1—P1—O3	110.39 (10)	O4—P2—O6	106.37 (9)
O2—P1—C1	109.12 (9)	O5—P2—C4	106.28 (8)
O1—P1—C1	106.29 (9)	O4—P2—C4	109.81 (9)
O3—P1—C1	102.78 (10)	O6—P2—C4	103.89 (8)
P1—O3—H3D	124.9 (18)	P2—O6—H6A	116.1 (16)
C1—N1—H1	110.3 (14)	C4—N2—H4	111.8 (14)
C1—N1—H2	107.5 (15)	C4—N2—H5	108.2 (14)
H1—N1—H2	110.3 (12)	H4—N2—H5	108.1 (12)
C1—N1—H3	109.2 (14)	C4—N2—H6	112.1 (14)
H1—N1—H3	110.3 (12)	H4—N2—H6	108.3 (12)
H2—N1—H3	109.2 (12)	H5—N2—H6	108.1 (11)
N1—C1—C2	110.49 (17)	N2—C4—C5	111.50 (17)
N1—C1—P1	109.52 (13)	N2—C4—P2	109.09 (13)
C2—C1—P1	115.69 (16)	C5—C4—P2	113.58 (15)
N1—C1—H1A	106.9	N2—C4—H4A	107.5
C2—C1—H1A	106.9	C5—C4—H4A	107.5
P1—C1—H1A	106.9	P2—C4—H4A	107.5
C3—C2—C1	113.07 (19)	C4—C5—C6	113.4 (2)
C3—C2—H2A	109.0	C4—C5—H5A	108.9
C1—C2—H2A	109.0	C6—C5—H5A	108.9
C3—C2—H2B	109.0	C4—C5—H5B	108.9
C1—C2—H2B	109.0	C6—C5—H5B	108.9
H2A—C2—H2B	107.8	H5A—C5—H5B	107.7
C2—C3—H3A	109.5	C5—C6—H6B	109.5
C2—C3—H3B	109.5	C5—C6—H6C	109.5
H3A—C3—H3B	109.5	H6B—C6—H6C	109.5
C2—C3—H3C	109.5	C5—C6—H6D	109.5
H3A—C3—H3C	109.5	H6B—C6—H6D	109.5
H3B—C3—H3C	109.5	H6C—C6—H6D	109.5
O2—P1—C1—N1	26.71 (17)	O5—P2—C4—N2	36.46 (15)
O1—P1—C1—N1	151.89 (14)	O4—P2—C4—N2	−89.49 (14)
O3—P1—C1—N1	−92.10 (15)	O6—P2—C4—N2	157.07 (12)
O2—P1—C1—C2	152.35 (15)	O5—P2—C4—C5	161.50 (14)
O1—P1—C1—C2	−82.47 (17)	O4—P2—C4—C5	35.56 (17)
O3—P1—C1—C2	33.53 (18)	O6—P2—C4—C5	−77.88 (16)
N1—C1—C2—C3	−170.11 (19)	N2—C4—C5—C6	−65.7 (2)
P1—C1—C2—C3	64.8 (2)	P2—C4—C5—C6	170.61 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3D···O4i	0.94 (1)	1.66 (1)	2.583 (2)	168 (3)
N1—H1···O1ii	0.94 (1)	1.83 (1)	2.767 (2)	178 (2)
N1—H2···O2iii	0.95 (1)	1.97 (2)	2.794 (2)	144 (2)
N1—H3···O4iv	0.95 (1)	1.91 (1)	2.843 (3)	166 (2)
O6—H6A···O1	0.94 (1)	1.65 (1)	2.589 (2)	175 (3)
N2—H4···O4v	0.95 (1)	2.05 (2)	2.914 (2)	151 (2)
N2—H5···O5vi	0.95 (1)	1.78 (1)	2.697 (2)	162 (2)
N2—H6···O2vi	0.95 (1)	1.84 (1)	2.783 (2)	172 (2)

Table 1

Selected torsion angles (°)

O3—P1—C1—C2	33.53 (18)
P1—C1—C2—C3	64.8 (2)
O6—P2—C4—C5	−77.88 (16)
P2—C4—C5—C6	170.61 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3D⋯O4i	0.94 (1)	1.66 (1)	2.583 (2)	168 (3)
N1—H1⋯O1ii	0.94 (1)	1.83 (1)	2.767 (2)	178 (2)
N1—H2⋯O2iii	0.95 (1)	1.97 (2)	2.794 (2)	144 (2)
N1—H3⋯O4iv	0.95 (1)	1.91 (1)	2.843 (3)	166 (2)
O6—H6A⋯O1	0.94 (1)	1.65 (1)	2.589 (2)	175 (3)
N2—H4⋯O4v	0.95 (1)	2.05 (2)	2.914 (2)	151 (2)
N2—H5⋯O5vi	0.95 (1)	1.78 (1)	2.697 (2)	162 (2)
N2—H6⋯O2vi	0.95 (1)	1.84 (1)	2.783 (2)	172 (2)

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