Crystal structure of bis­[(1-ammonio-1-phosphono­eth­yl)phospho­nato]tetra­aqua­cadmium dihydrate: a powder X-ray diffraction study

Rukiah, M.; Assaad, T.

doi:10.1107/S2056989015004028

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ISSN: 2056-9890

Volume 71| Part 4| April 2015| Pages 342-345

doi:10.1107/S2056989015004028

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Crystal structure of bis[(1-ammonio-1-phosphonoethyl)phosphonato]tetraaquacadmium dihydrate: a powder X-ray diffraction study

Mwaffak Rukiah ^a ^* and Thaer Assaad ^b

^aDepartment of Chemistry, Atomic Energy Commission of Syria (AECS), PO Box 6091, Damascus, Syrian Arab Republic, and ^bRadioisotope Department, Atomic Energy Commission of Syria (AECS), PO Box 6091, Damascus, Syrian Arab Republic
^*Correspondence e-mail: cscientific@aec.org.sy

Edited by V. V. Chernyshev, Moscow State University, Russia (Received 3 February 2015; accepted 26 February 2015; online 7 March 2015)

In the title compound, [CdL₂(H₂O)₄]·2H₂O [L = (1-ammonio-1-phosphonoethyl)phosphonate, C₂H₈NO₆P₂⁻], the Cd^II ion is situated on an inversion centre being coordinated by four aqua molecules in the equatorial plane and two phosphonate O atoms from two deprotonated L ligands in the axial positions in a distorted octahedral geometry. The asymmetric unit contains one-half of the complex molecule and one lattice water molecule. The ligand L exists in a zwitterionic form, with a positive charge on the NH₃ group and a negative charge on the O atom of the non-coordinating phosphonate group, and with an intramolecular O—H⋯O interaction forming an S(6) ring motif and two intramolecular N—H⋯O interactions each generating an S(5) ring motif. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the complex molecules into a three-dimensional network in which the voids of 38 Å³ are filled with ordered lattice water molecules, which are also involved in O—H⋯O hydrogen bonding.

Keywords: crystal structure; bisphosphonate complexes; complexes; cadmium; powder diffraction; octahedral coordination; zwitterion; hydrogen bonding.

CCDC reference: 1051338

1. Chemical context

As a result of of their inhibitory effect on bone resorption, various types of bisphosphonates are used in the treatment of bone metastasis and several bone disorders such as Paget's disease, and for the prevention of osteoporosis in post-menopausal women (Shaw & Bishop, 2005 ). Drugs prepared on the basis of bisphosphonates are highly efficient as a regulator of calcium metabolism and the immune response; they are used as anti-neoplastic, anti-inflammatory and antiviral agents, drugs with analgesic effect and, as a component of toothpastes, biphosphonates prevent the formation of tartar (Matkovskaya et al., 2001 ). Organic diphosphonic acids are potentially very powerful chelating agents, used in metal extractions and have been tested by the pharmaceutical industry for use as efficient drugs preventing calcification and inhibiting bone resorption (Matczak-Jon & Videnova-Adrabińska, 2005 ). Diphosphonic acids and their metal complexes are used in the treatment of Paget's disease, osteoporosis and tumoral osteolysis (Szabo et al., 2002 ). However, it is still not clearly understood why small structural modification of bisphosphonates may lead to extensive alterations in their physicochemical, biological and toxicological characteristics (Matczak-Jon & Videnova-Adrabińska, 2005). Therefore, the structure determination of bisphosphonates is very important in order to understand the influence of structural modifications on their complex-forming abilities and physiological activities.

2. Structural commentary

The asymmetric unit of the title compound, (I) (Fig. 1), contains one half of the complex molecule [CdL₂(H₂O)₄] [L = (1-ammonio-1-phosphonoethyl)phosphonate] and one lattice water molecule. All bond lengths and angles in (I) are normal and correspond to those observed in bisphosphonate complexes with transition metals (Shkol'nikova et al., 1991 ; Sergienko et al., 1997 , 1999 ; Yin et al., 2005 ; Li et al., 2006 ; Li & Sun, 2007 ; Lin et al., 2007 ; Xiang et al., 2007 ; Dudko et al., 2009 , 2010 ; Bon et al., 2010 ; Tsaryk et al., 2010 , 2011 ). The Cd^II atom occupies a special position on an inversion centre and shows a slightly distorted octahedral coordination environment formed by two phosphonic O atoms in trans positions and four aqua O atoms in the equatorial plane. The distorted octahedral coordination polyhedron is slightly compressed in the axial direction; the Cd1—O2 bond length is 0.1 Å shorter than the Cd1—O1W and Cd1—O2W bonds. The values of the axial O—Cd—O angles are in the range 80.1 (4)–99.9 (4)°, indicating a significant deviation from ideal values. The ligand L exists in a zwitterionic form, with a positive charge on the NH₃ group and a negative charge on the O atom of the non-coordinating phosphonate group, and with an intramolecular O—H⋯O interaction forming an S(6) ring motif and two intramolecular N—H⋯O interactions each generating an S(5) ring motif (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4	0.84	2.44	3.196 (13)	151
N1—H1NA⋯O6ⁱ	0.87	2.07	2.828 (13)	146
N1—H1NB⋯O4ⁱⁱ	0.88	2.16	2.872 (15)	137
N1—H1NC⋯O3ⁱ	0.86	1.99	2.796 (14)	156
O1W—H1W1⋯O2Wⁱ	0.82	2.39	2.987 (13)	131
O5—H5⋯O6ⁱⁱⁱ	0.84	1.79	2.551 (12)	150
O1W—H2W1⋯O3ⁱ	0.82	1.96	2.758 (15)	162
O2W—H2W2⋯O4^iv	0.82	2.35	3.141 (15)	162
O3W—H1W3⋯O3W^v	0.82	2.56	3.346 (13)	160
O3W—H2W3⋯O3^vi	0.82	2.13	2.833 (14)	143
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z+1; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x+1, y, z; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
The molecular structure of (I)

, showing the atom-labelling scheme [symmetry code: (i) −x + 1, −y + 1, −z + 1]. Displacement spheres are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii. Dotted lines denote hydrogen bonds.

3. Supramolecular features

The crystal packing is illustrated in Fig. 2 as a projection of the unit cell along the b axis. Intermolecular N—H⋯O and O—H⋯O hydrogen bonds (Table 1) link complex molecules into a three-dimensional network in which the voids of 38 Å³ are filled with ordered lattice water molecules, which are also involved in O—H⋯O hydrogen bonding (Table 1 and Fig. 2).

Figure 2
A portion of the crystal packing viewed down the b axis. Dashed lines denote hydrogen bonds.

4. Synthesis and crystallization

All reactions and manipulations were carried out in air with reagent grade solvents. 1-Aminoethane-1,1-diyldiphosphonic acid was prepared according to the literature method of Rukiah & Assaad (2013 ). The title compound (I) was prepared by adding 10 ml of an 0.01 M CdCl₂ aqueous solution to 10 ml of a 0.02 M water solution of 1-aminoethane-1,1-diyldiphosphonic acid. A crude product was obtained after two weeks of slow evaporation of the resulted solution. It was further purified by recrystallization from ethanol and water (1:3 v/v) at 273 K to produce the title compound (I) (white powder; m.p. > 623 K) in 80% yield. The IR spectrum was recorded on a Jasco FT–IR 300E instrument and the ¹H and ¹³C{¹H} NMR spectra were recorded on a Bruker Bio spin 400 spectrometer.

Spectroscopic data for (I):

¹H NMR (D₂O, p.p.m.): δ 1.67 (t, 3H, CH₃, J = 14 Hz). ¹³C{¹H} NMR (D₂O, p.p.m.): δ 20.5 (1C; CH₃), 54.7 (1C; C—CH₃). ³¹P{¹H} NMR (D₂O, p.p.m.): δ 13.61(2P; P—OH). IR (KBr, ν cm⁻¹): 3446.2 (NH₃), 2351.5 (POH), 1605.0 (O=P—O—H).

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Compound (I) has a tendency to crystallize in the form of a very fine white powder. Since no single crystals of sufficient size and quality could be obtained, a crystal structure determination from laboratory powder X-ray diffraction data was performed. The powder sample was ground slightly in a mortar, loaded into two Mylar foils and fixed onto the sample holder with a mask of suitable internal diameter (8.0 mm). The powder X-ray diffraction data were collected at room temperature with a STOE transmission STADI-P diffractometer using CuK_α1 radiation (λ= 1.54060 Å) selected with an incident-beam curved-crystal Ge(111) monochromator with a linear position-sensitive detector (PSD). The pattern was scanned over the angular range 6.0–90.0° (2θ). For pattern indexing, extraction of the peak positions was carried out with the program WinPLOTR (Roisnel & Rodríguez-Carvajal, 2001 ). Pattern indexing was performed with the program DICVOL4.0 (Boultif & Louër, 2004 ). The first 20 intense peaks of the powder pattern were indexed completely on the basis of a monoclinic cell. The figures of merit (de Wolff et al., 1968 ; Smith & Snyder, 1979 ) are sufficiently acceptable to support the obtained indexing results [M(20) = 37.1, F(20) = 78.5(0.0061, 42)]. The best estimated monoclinic space group was P2₁/c.

Table 2
Experimental details

Crystal data
Chemical formula	[Cd(C₂H₈NO₆P₂)₂(H₂O)₄]·2H₂O
M_r	628.57
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.69424 (12), 5.61453 (5), 17.2737 (2)
β (°)	100.7029 (8)
V (Å³)	1019.12 (2)
Z	2
Radiation type	Cu Kα₁, λ = 1.5406 Å
μ (mm⁻¹)	12.41
Specimen shape, size (mm)	Flat sheet, 8 × 8

Data collection
Diffractometer	Stoe transmission STADI-P
Specimen mounting	Powder loaded into two Mylar foils
Data collection mode	Transmission
Scan method	Step
Absorption correction	For a cylinder mounted on the φ axis [GSAS (Larson & Von Dreele, 2004) absorption/surface roughness correction: function No. 4, flat-plate transmission absorption correction, terms = 0.75850]
T_min, T_max	0.195, 0.310
2θ values (°)	2θ_min = 6.00 2θ_max = 89.98 2θ_step = 0.02

Refinement
R factors and goodness of fit	R_p = 0.029, R_wp = 0.039, R_exp = 0.025, R(F²) = 0.04534, χ² = 2.624
No. of data points	4100
No. of parameters	133
No. of restraints	4
H-atom treatment	H-atom parameters not refined
Computer programs: WinXPOW (Stoe & Cie, 1999 ), GSAS (Larson & Von Dreele, 2004), EXPO2014 (Altomare et al., 2013), Mercury (Macrae et al., 2006 ) and publCIF (Westrip, 2010 ).

The powder pattern was subsequently refined with cell and resolution constraints (Le Bail et al., 1988 ) using the profile-matching option of the program FULLPROF (Rodríguez-Carvajal, 2001 $[Rodríguez-Carvajal, J. (2001). Commission on Powder Diffraction (IUCr) Newsletter, 26, 12-19.]$ ). The number of molecules per unit cell was estimated to be Z = 2. The initial crystal structure was determined by direct methods using the program EXPO2014 (Altomare et al., 2013 ). The model found by this program was introduced into the program GSAS (Larson & Von Dreele, 2004 ) implemented in EXPGUI (Toby, 2001 ) for Rietveld refinement. The background was refined using a shifted Chebyshev polynomial with 20 coefficients. The effect of the asymmetry of the low-order peaks was corrected using a pseudo-Voigt description of the peak shape (Thompson et al., 1987 ), angle-dependent asymmetry with axial divergence (Finger et al., 1994 ) and microstrain broadening (Stephens, 1999 ). Two asymmetry parameters of this function, S/L and D/L, were both fixed at 0.0225 during this refinement. Intensities were corrected for absorption effects with a function for a plate sample in transmission geometry with μ·d value of 0.7585 (μ is the absorption coefficient and d is the sample thickness). These μ·d values were determined experimentally. The preferred orientation was modelled with 12 coefficients using a spherical harmonics correction (Von Dreele, 1997 ) of intensities. The use of the preferred orientation correction leads to a better molecular geometry with better agreement factors. The value of obtained median texture index (1.0654) and the agreement factors in the refinement without texture correction (R_p = 0.053, R_wp = 0.073, R_exp = 0.025, R(F²) = 0.011009 and χ² = 8.940) indicate that the preferred orientation improvement of the refinement is considerable.

Before the final refinement, the H atoms of the CH₃ and NH₃ groups were introduced on the basis of geometrical arguments. The hydroxy and water H atoms were located using the program HYDROGEN (Nardelli, 1999 ) implemented in WinGX (Farrugia, 2012 ). The coordinates of all H atoms were refined with very strict soft restraints on bond lengths and angle until a suitable geometry was obtained, after that they were fixed in the final stage of the refinement. Four restraints for the central carbon atom (C—CH₃, C—NH₃ and two C—PO₃) on bond lengths were applied to normal values for these bonds. The final refinement cycles were performed varying isotropic displacement parameters for Cd and water O atoms, and fixed isotropic displacement parameters for P, C, N,O and H atoms. The final Rietveld plot is shown in Fig. 3.

Figure 3
The final Rietveld plot for (I)

. Experimental intensities are indicated by dots, and the best-fit calculated (upper trace) and difference (lower trace) patterns are shown as solid lines. The vertical bars indicate the calculated positions of the Bragg peaks.

Supporting information

CCDC reference: 1051338

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015004028/cv5484sup1.cif

Rietveld powder data: contains datablock I. DOI: 10.1107/S2056989015004028/cv5484Isup2.rtv

checkCIF report

Computing details top

Data collection: WinXPOW (Stoe & Cie, 1999); cell refinement: GSAS (Larson & Von Dreele, 2004); data reduction: WinXPOW (Stoe & Cie, 1999); program(s) used to solve structure: EXPO2014 (Altomare et al., 2013); program(s) used to refine structure: GSAS (Larson & Von Dreele, 2004); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis[(1-ammonio-1-phosphonoethyl)phosphonato]tetraaquacadmium dihydrate top

Crystal data top

[Cd(C₂H₈NO₆P₂)₂(H₂O)₄]·2H₂O	Z = 2
M_r = 628.57	F(000) = 636
Monoclinic, P2₁/c	D_x = 2.048 Mg m⁻³
Hall symbol: -P 2ybc	Cu Kα₁ radiation, λ = 1.5406 Å
a = 10.69424 (12) Å	µ = 12.41 mm⁻¹
b = 5.61453 (5) Å	T = 298 K
c = 17.2737 (2) Å	Particle morphology: fine powder
β = 100.7029 (8)°	white
V = 1019.12 (2) Å³	flat_sheet, 8 × 8 mm

Data collection top

Stoe transmission STADI-P diffractometer	Scan method: step
Radiation source: sealed X-ray tube	Absorption correction: for a cylinder mounted on the φ axis [GSAS (Larson & Von Dreele, 2004) absorption/surface roughness correction: function No. 4, flat-plate transmission absorption correction, terms = 0.75850]
Ge 111 monochromator	T_min = 0.195, T_max = 0.310
Specimen mounting: Powder loaded into two Mylar foils	2θ_min = 6.00°, 2θ_max = 89.98°, 2θ_step = 0.02°
Data collection mode: transmission

Refinement top

Refinement on I_net	Profile function: CW Profile function number 4 with 21 terms Pseudovoigt profile coefficients as parameterized in (Thompson et al., 1987). Asymmetry correction of (Finger et al., 1994). Microstrain broadening by (Stephens, 1999). #1(GU) = 0.000 #2(GV) = 0.000 #3(GW) = 7.136 #4(GP) = 0.000 #5(LX) = 2.421 #6(ptec) = 0.11 #7(trns) = 0.00 #8(shft) = 0.0000 #9(sfec) = 0.00 #10(S/L) = 0.0225 #11(H/L) = 0.0225 #12(eta) = 0.6026 #13(S400 ) = 1.2E-02 #14(S040 ) = 1.0E-01 #15(S004 ) = 1.2E-03 #16(S220 ) = 3.3E-02 #17(S202 ) = 6.7E-03 #18(S022 ) = 1.7E-02 #19(S301 ) = 1.1E-02 #20(S103 ) = 2.3E-03 #21(S121 ) = 1.5E-02 Peak tails are ignored where the intensity is below 0.0010 times the peak Aniso. broadening axis 0.0 0.0 1.0
Least-squares matrix: full	133 parameters
R_p = 0.029	4 restraints
R_wp = 0.039	H-atom parameters not refined
R_exp = 0.025	Weighting scheme based on measured s.u.'s
R(F²) = 0.04534	(Δ/σ)_max = 0.03
4100 data points	Background function: GSAS Background function number 1 with 20 terms. Shifted Chebyshev function of 1st kind 1: 1216.00 2: -1325.95 3: 695.908 4: -224.478 5: 51.5854 6: -12.9254 7: 7.98937 8: -13.4593 9: 4.35490 10: 32.6578 11: -32.8988 12: -6.52632 13: -18.8133 14: 23.4504 15: -2.70081 16: -0.874623 17: -28.0163 18: 27.3423 19: 2.28961 20: -11.2631

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1555 (5)	0.3764 (12)	0.6381 (5)	0.015*
C2	0.2285 (11)	0.4133 (17)	0.7222 (5)	0.015*
H2a	0.17609	0.50488	0.75213	0.02*
H2b	0.3063	0.50177	0.72104	0.02*
H2c	0.24919	0.26144	0.74755	0.02*
N1	0.1274 (11)	0.6170 (16)	0.6028 (7)	0.02*
H1na	0.07228	0.68814	0.62561	0.025*
H1nb	0.09382	0.59823	0.55236	0.025*
H1nc	0.19624	0.69829	0.60678	0.025*
P1	0.2594 (5)	0.2361 (7)	0.5774 (3)	0.01*
O1	0.1897 (8)	0.2047 (13)	0.4907 (6)	0.01*
H1	0.11151	0.1887	0.48952	0.015*
O2	0.3659 (9)	0.4155 (15)	0.5771 (6)	0.01*
O3	0.3024 (8)	−0.0094 (16)	0.6124 (6)	0.01*
P2	0.0019 (4)	0.2252 (6)	0.6342 (3)	0.01*
O4	−0.0728 (9)	0.1904 (14)	0.5539 (6)	0.01*
O5	−0.0807 (8)	0.4058 (11)	0.6745 (5)	0.01*
H5	−0.06622	0.38276	0.7235	0.03*
O6	0.0255 (7)	−0.0022 (16)	0.6785 (5)	0.01*
Cd1	0.5	0.5	0.5	0.0093 (7)*
O1W	0.5302 (11)	0.8211 (15)	0.5815 (7)	0.029 (4)*
H1W1	0.56	0.91732	0.55443	0.03*
H2W1	0.47216	0.89419	0.59649	0.03*
O2W	0.6537 (10)	0.2995 (14)	0.5866 (6)	0.020 (3)*
H1W2	0.63758	0.22791	0.62489	0.03*
H2W2	0.72024	0.23865	0.57871	0.03*
O3w	0.5739 (11)	0.3949 (14)	0.7310 (6)	0.028 (3)*
H1W3	0.54032	0.26314	0.72841	0.03*
H2W3	0.5752	0.43812	0.77663	0.03*

Geometric parameters (Å, º) top

C1—C2	1.530 (12)	P2—O5	1.588 (7)
C1—N1	1.490 (12)	P2—O6	1.486 (9)
C1—P1	1.840 (9)	O5—H5	0.842
C1—P2	1.839 (7)	Cd1—O2	2.183 (8)
C2—H2a	0.976	Cd1—O2ⁱ	2.183 (8)
C2—H2b	0.972	Cd1—O1W	2.274 (9)
C2—H2c	0.965	Cd1—O1Wⁱ	2.274 (9)
N1—H1na	0.865	Cd1—O2W	2.300 (10)
N1—H1nb	0.885	Cd1—O2Wⁱ	2.300 (10)
N1—H1nc	0.858	O1W—H1W1	0.817
P1—O1	1.555 (11)	O1W—H2W1	0.824
P1—O2	1.521 (9)	O2W—H1W2	0.820
P1—O3	1.541 (9)	O2W—H2W2	0.823
O1—H1	0.838	O3w—H1W3	0.820
P2—O4	1.480 (10)	O3w—H2W3	0.823

C2—C1—N1	107.2 (7)	C1—P2—O6	108.2 (5)
C2—C1—P1	110.1 (6)	O4—P2—O5	104.3 (5)
C2—C1—P2	113.1 (7)	O4—P2—O6	112.3 (6)
N1—C1—P1	104.6 (5)	O5—P2—O6	112.2 (5)
N1—C1—P2	107.0 (6)	P2—O5—H5	109.2
P1—C1—P2	114.3 (4)	O2—Cd1—O2ⁱ	180.0
C1—C2—H2a	109.4	O2—Cd1—O1W	80.1 (4)
C1—C2—H2b	109.6	O2—Cd1—O1Wⁱ	99.9 (4)
C1—C2—H2c	110.1	O2—Cd1—O2W	88.2 (3)
H2a—C2—H2b	108.6	O2—Cd1—O2Wⁱ	91.8 (3)
H2a—C2—H2c	109.4	O2ⁱ—Cd1—O1W	99.9 (4)
H2b—C2—H2c	109.7	O2ⁱ—Cd1—O1Wⁱ	80.1 (4)
C1—N1—H1na	109.5	O2ⁱ—Cd1—O2W	91.8 (3)
C1—N1—H1nb	108.0	O2ⁱ—Cd1—O2Wⁱ	88.2 (3)
C1—N1—H1nc	110.1	O1W—Cd1—O1Wⁱ	180.0
H1na—N1—H1nb	108.5	O1W—Cd1—O2W	89.0 (4)
H1na—N1—H1nc	111.4	O1W—Cd1—O2Wⁱ	91.0 (4)
H1nb—N1—H1nc	109.1	O1Wⁱ—Cd1—O2W	91.0 (4)
C1—P1—O1	111.5 (6)	O1Wⁱ—Cd1—O2Wⁱ	89.0 (4)
C1—P1—O2	104.5 (5)	O2W—Cd1—O2Wⁱ	180.0
C1—P1—O3	109.1 (4)	Cd1—O1W—H1W1	101.2
O1—P1—O2	107.2 (5)	Cd1—O1W—H2W1	124.1
O1—P1—O3	109.4 (5)	H1W1—O1W—H2W1	104.3
O2—P1—O3	115.1 (6)	Cd1—O2W—H1W2	122.2
P1—O1—H1	109.4	Cd1—O2W—H2W2	129.1
P1—O2—Cd1	136.4 (6)	H1W2—O2W—H2W2	104.3
C1—P2—O4	114.8 (5)	H1W3—O3w—H2W3	104.3
C1—P2—O5	104.8 (4)

O1W—Cd1—O2—P1	168.8 (9)	O1—P1—C1—C2	−177.9 (6)
O2W—Cd1—O2—P1	−101.9 (8)	O2—P1—C1—C2	−62.3 (7)
O1Wⁱ—Cd1—O2—P1	−11.2 (9)	O3—P1—C1—C2	61.3 (7)
O2Wⁱ—Cd1—O2—P1	78.1 (8)	O4—P2—C1—P1	−54.2 (6)
O3—P1—O2—Cd1	84.9 (9)	O5—P2—C1—P1	−168.0 (5)
C1—P1—O2—Cd1	−155.4 (7)	O6—P2—C1—P1	72.1 (6)
O1—P1—O2—Cd1	−37.0 (9)	O4—P2—C1—N1	61.1 (8)
O1—P1—C1—P2	53.6 (6)	O5—P2—C1—N1	−52.7 (8)
O2—P1—C1—P2	169.2 (5)	O6—P2—C1—N1	−172.6 (7)
O3—P1—C1—P2	−67.2 (6)	O4—P2—C1—C2	178.9 (6)
O1—P1—C1—N1	−63.1 (7)	O5—P2—C1—C2	65.0 (7)
O2—P1—C1—N1	52.5 (8)	O6—P2—C1—C2	−54.9 (7)
O3—P1—C1—N1	176.1 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.84	2.44	3.196 (13)	151
O1—H1···O4ⁱⁱ	0.84	2.27	2.592 (12)	103
N1—H1NA···O5	0.87	2.53	2.986 (14)	114
N1—H1NA···O6ⁱⁱⁱ	0.87	2.07	2.828 (13)	146
N1—H1NB···O4^iv	0.88	2.16	2.872 (15)	137
N1—H1NC···O2	0.86	2.53	2.899 (15)	107
N1—H1NC···O3ⁱⁱⁱ	0.86	1.99	2.796 (14)	156
O1W—H1W1···O2Wⁱⁱⁱ	0.82	2.39	2.987 (13)	131
O5—H5···O6^v	0.84	1.79	2.551 (12)	150
O1W—H2W1···O3ⁱⁱⁱ	0.82	1.96	2.758 (15)	162
O2W—H1W2···O3W	0.82	2.27	2.833 (15)	126
O2W—H2W2···O4^vi	0.82	2.35	3.141 (15)	162
O3W—H1W3···O3W^vii	0.82	2.56	3.346 (13)	160
O3W—H2W3···O3^viii	0.82	2.13	2.833 (14)	143

Symmetry codes: (ii) −x, −y, −z+1; (iii) x, y+1, z; (iv) −x, −y+1, −z+1; (v) −x, y+1/2, −z+3/2; (vi) x+1, y, z; (vii) −x+1, y−1/2, −z+3/2; (viii) −x+1, y+1/2, −z+3/2.

Acknowledgements

We thank Professor I. Othman, Director General, Professor Z. Ajii, Head of the Chemistry Department, and Professor A. H. Al-Rayyes, Head of the Radioisotope Department, for their support of this work. We also thank Mr Emad Ghanem and Madame Najwa Karajoli for their kind assistance with the laboratory work.

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