P,P'-Diphenyl-ethyl-enediphosphinic acid dihydrate.

The title compound, C(14)H(16)O(4)P(2)·2H(2)O, possesses a crystallographic inversion center where two -P(=O)(OH)(C(6)H(5)) groups are joined together via two -CH(2) groups. In the crystal, the acid molecules are linked by the water molecules via O-H⋯O hydrogen bonds, leading to the formation of a two-dimensional network lying parallel to (101).

Related literature

For background on related phosphine macrocycles, see: Caminade & Majoral (1994 ▶); Swor & Tyler (2011 ▶). For related syntheses, see: Lambert & Desreux (2000 ▶). For literature related to the use of phosphine complexes as N2 scrubbers, see: Miller et al. (2002 ▶). For a related structure, see: Costantino et al. (2008 ▶). For literature related to the macrocycle effect, see: Melson (1979 ▶).

Experimental

Crystal data

C14H16O4P2·2H2O

M = 346.24

Monoclinic,

a = 10.8280 (16) Å

b = 6.2455 (10) Å

c = 12.861 (2) Å

β = 91.177 (2)°

V = 869.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 173 K

0.27 × 0.23 × 0.12 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.930, T max = 0.968

9251 measured reflections

1888 independent reflections

1696 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.09

1888 reflections

112 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812030954/bv2207sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030954/bv2207Isup2.hkl

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

C14H16O4P2·2H2O	F(000) = 364
Mr = 346.24	Dx = 1.322 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4007 reflections
a = 10.8280 (16) Å	θ = 2.4–28.0°
b = 6.2455 (10) Å	µ = 0.27 mm−1
c = 12.861 (2) Å	T = 173 K
β = 91.177 (2)°	Block, colorless
V = 869.5 (2) Å3	0.27 × 0.23 × 0.12 mm
Z = 2

Bruker APEX CCD area-detector diffractometer	1888 independent reflections
Radiation source: fine-focus sealed tube	1696 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
Tmin = 0.930, Tmax = 0.968	k = −7→7
9251 measured reflections	l = −16→16

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0533P)2 + 0.4488P] where P = (Fo2 + 2Fc2)/3
1888 reflections	(Δ/σ)max < 0.001
112 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.39 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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	0.84023 (4)	0.19271 (7)	0.54585 (3)	0.02826 (16)
O1	0.77895 (12)	0.0487 (2)	0.62175 (10)	0.0395 (3)
O2	0.92075 (11)	0.3728 (2)	0.59502 (10)	0.0368 (3)
C1	0.94816 (15)	0.0518 (3)	0.46715 (13)	0.0318 (4)
H1B	0.9039	−0.0607	0.4270	0.038*
H1C	0.9847	0.1527	0.4170	0.038*
C2	0.72834 (16)	0.3127 (3)	0.45984 (14)	0.0356 (4)
C3	0.6126 (2)	0.2218 (6)	0.4494 (2)	0.0835 (10)
H3A	0.5926	0.0983	0.4887	0.100*
C4	0.5256 (3)	0.3103 (9)	0.3818 (3)	0.1219 (18)
H4A	0.4467	0.2452	0.3737	0.146*
C5	0.5523 (3)	0.4894 (7)	0.3271 (2)	0.0949 (12)
H5A	0.4910	0.5519	0.2827	0.114*
C6	0.6673 (3)	0.5807 (5)	0.3356 (2)	0.0762 (8)
H6A	0.6861	0.7047	0.2961	0.091*
C7	0.7566 (2)	0.4916 (4)	0.40205 (17)	0.0526 (5)
H7A	0.8366	0.5537	0.4076	0.063*
O1S	0.8284 (2)	0.6587 (3)	0.69946 (14)	0.0622 (5)
H1O	0.875 (2)	0.491 (4)	0.6401 (19)	0.062 (7)*
H1S	0.792 (3)	0.621 (5)	0.756 (3)	0.086 (10)*
H2S	0.801 (3)	0.783 (6)	0.670 (3)	0.092 (10)*

	U11	U22	U33	U12	U13	U23
P1	0.0299 (2)	0.0269 (3)	0.0281 (2)	0.00257 (16)	0.00540 (16)	0.00037 (15)
O1	0.0459 (7)	0.0341 (7)	0.0390 (7)	0.0028 (6)	0.0142 (6)	0.0059 (5)
O2	0.0347 (6)	0.0363 (7)	0.0395 (7)	0.0003 (5)	0.0030 (5)	−0.0077 (6)
C1	0.0347 (9)	0.0328 (9)	0.0280 (8)	0.0056 (7)	0.0050 (7)	−0.0023 (7)
C2	0.0308 (9)	0.0425 (10)	0.0337 (9)	0.0061 (7)	0.0022 (7)	0.0010 (7)
C3	0.0406 (12)	0.131 (3)	0.0778 (18)	−0.0223 (16)	−0.0133 (12)	0.0428 (19)
C4	0.0413 (14)	0.226 (5)	0.097 (2)	−0.011 (2)	−0.0203 (15)	0.066 (3)
C5	0.0592 (17)	0.166 (4)	0.0587 (16)	0.044 (2)	−0.0078 (13)	0.028 (2)
C6	0.103 (2)	0.0722 (18)	0.0535 (14)	0.0296 (17)	−0.0077 (14)	0.0196 (13)
C7	0.0597 (13)	0.0459 (12)	0.0518 (12)	0.0027 (10)	−0.0082 (10)	0.0102 (10)
O1S	0.1045 (15)	0.0336 (8)	0.0501 (9)	0.0127 (8)	0.0378 (10)	0.0049 (7)

P1—O1	1.4928 (13)	C3—H3A	0.9500
P1—O2	1.5500 (13)	C4—C5	1.355 (5)
P1—C2	1.7883 (18)	C4—H4A	0.9500
P1—C1	1.7927 (16)	C5—C6	1.373 (5)
O2—H1O	1.06 (3)	C5—H5A	0.9500
C1—C1i	1.534 (3)	C6—C7	1.393 (3)
C1—H1B	0.9900	C6—H6A	0.9500
C1—H1C	0.9900	C7—H7A	0.9500
C2—C7	1.380 (3)	O1S—H1O	1.40 (3)
C2—C3	1.380 (3)	O1S—H1S	0.87 (3)
C3—C4	1.383 (4)	O1S—H2S	0.91 (4)
O1—P1—O2	115.11 (8)	C2—C3—H3A	119.9
O1—P1—C2	110.63 (8)	C4—C3—H3A	119.9
O2—P1—C2	108.45 (8)	C5—C4—C3	120.4 (3)
O1—P1—C1	112.15 (8)	C5—C4—H4A	119.8
O2—P1—C1	102.64 (8)	C3—C4—H4A	119.8
C2—P1—C1	107.32 (8)	C4—C5—C6	120.3 (2)
P1—O2—H1O	117.6 (14)	C4—C5—H5A	119.9
C1i—C1—P1	111.97 (15)	C6—C5—H5A	119.9
C1i—C1—H1B	109.2	C5—C6—C7	120.0 (3)
P1—C1—H1B	109.2	C5—C6—H6A	120.0
C1i—C1—H1C	109.2	C7—C6—H6A	120.0
P1—C1—H1C	109.2	C2—C7—C6	119.7 (2)
H1B—C1—H1C	107.9	C2—C7—H7A	120.2
C7—C2—C3	119.5 (2)	C6—C7—H7A	120.2
C7—C2—P1	121.16 (15)	H1O—O1S—H1S	116 (2)
C3—C2—P1	119.37 (18)	H1O—O1S—H2S	122 (2)
C2—C3—C4	120.1 (3)	H1S—O1S—H2S	116 (3)
O1—P1—C1—C1i	−60.33 (19)	C7—C2—C3—C4	−0.3 (5)
O2—P1—C1—C1i	63.78 (18)	P1—C2—C3—C4	−178.9 (3)
C2—P1—C1—C1i	177.97 (16)	C2—C3—C4—C5	−1.5 (6)
O1—P1—C2—C7	162.61 (16)	C3—C4—C5—C6	2.2 (6)
O2—P1—C2—C7	35.49 (19)	C4—C5—C6—C7	−1.2 (5)
C1—P1—C2—C7	−74.74 (18)	C3—C2—C7—C6	1.3 (4)
O1—P1—C2—C3	−18.8 (3)	P1—C2—C7—C6	179.83 (19)
O2—P1—C2—C3	−146.0 (2)	C5—C6—C7—C2	−0.6 (4)
C1—P1—C2—C3	103.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O···O1S	1.06 (3)	1.40 (3)	2.459 (2)	173 (2)
O1S—H1S···O1ii	0.87 (3)	1.82 (3)	2.687 (2)	178 (3)
O1S—H2S···O1iii	0.91 (4)	1.78 (4)	2.682 (2)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O⋯O1S	1.06 (3)	1.40 (3)	2.459 (2)	173 (2)
O1S—H1S⋯O1i	0.87 (3)	1.82 (3)	2.687 (2)	178 (3)
O1S—H2S⋯O1ii	0.91 (4)	1.78 (4)	2.682 (2)	167 (3)

Symmetry codes: (i) ; (ii) .