catena-Poly[sodium-di-μ-aqua-sodium-bis[μ-2,2,2-trichloro-N-(dimorpholinophosphoryl)acetamide]]

Litsis, O.O.; Ovchynnikov, V.A.; Sliva, T.Y.; Konovalova, I.S.; Amirkhanov, V.M.

doi:10.1107/S1600536810009670

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages m426-m427

doi:10.1107/S1600536810009670

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catena-Poly[sodium-di-μ-aqua-sodium-bis[μ-2,2,2-trichloro-N-(dimorpholinophosphoryl)acetamide]]

Olena O. Litsis,^a ^* Vladimir A. Ovchynnikov,^a Tetyana Yu. Sliva,^a Irina S. Konovalova ^b and Vladimir M. Amirkhanov ^a

^aKyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv, Ukraine, and ^bSTC "Institute for Single Crystals", National Academy of Science of Ukraine, Lenina ave. 60, 61001, Khar'kov, Ukraine
^*Correspondence e-mail: allicis@yahoo.com

(Received 11 March 2010; accepted 15 March 2010; online 20 March 2010)

The title compound, [Na₂(C₁₀H₁₆Cl₃N₃O₄P)₂(H₂O)₂]_n, can be considered as a two-dimensional coordination polymer in which one-dimensional chains are connected to each other by intermolecular C—H⋯O hydrogen bonds involving the water molecules. The Na^I ion is five-coordinated in a distorted trigonal-bipyramidal geometry. The connection between the two Na^I ions is facilitated by the two μ-O atoms of the carbonyl group of the 2,2,2-trichloro-N-(dimorpholinophosphoryl)acetamide (CAPh) ligand. A bridging coordination of the CAPh ligand via the carbonyl O atom is observed for the first time. The bridging water molecules form intermolecular O—H⋯O hydrogen bonds with the O atoms of the morpholine rings and the phosphoryl groups of neighboring CAPh molecules.

Related literature

For the pharmacological and biological properties of carbacylamidophosphate (CAPh) derivatives, see: Barak et al. (2000 ); Grimes et al. (2008 ); Adams et al. (2002 ); For structural analogues of phosphorylated carbacylamides and their coordination properties, see: Amirkhanov et al. (1996 ); Rebrova et al. (1982 ); Gubina et al. (1999 ); Ovchinnikov et al. (2001 ); Gholivand & Shariatinia (2006 ); Trush et al. (2005 ); Zhang et al. (1992 ). For details of the synthesis, see: Kirsanov & Derkach (1956 ). For the synthesis of the 2,2,2-trichloro-N-(dimorpholinophosphoryl)acetamide (HL) ligand, see: Ovchynnikov et al. (1998 ). For coordination compounds of HL, see: Ovchynnikov et al. (2000 ); Trush et al. (2002 , 2003 ). For the trigonality index τ, see: Addison et al. (1984 ).

Experimental

Crystal data

[Na₂(C₁₀H₁₆Cl₃N₃O₄P)₂(H₂O)₂]
M_r = 841.17
Triclinic, $[P \overline 1]$
a = 7.522 (5) Å
b = 10.329 (4) Å
c = 12.451 (5) Å
α = 84.17 (4)°
β = 80.89 (4)°
γ = 70.16 (5)°
V = 897.3 (8) Å³
Z = 1
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 294 K
0.40 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.782, T_max = 0.938
10258 measured reflections
5137 independent reflections
3339 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.121
S = 0.95
5137 reflections
236 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯O1ⁱ	0.97	2.59	3.443 (4)	147
O1W—H1WA⋯O3ⁱⁱ	0.98	1.77	2.716 (3)	163
O1W—H1WB⋯O2ⁱⁱⁱ	0.98	2.00	2.917 (3)	155
Symmetry codes: (i) -x-1, -y+1, -z+2; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009670/jh2135sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009670/jh2135Isup2.hkl

checkCIF report

Comment top

Carbacylamidophosphate compounds have been attracting substantial interest and are widely used to date. These compounds have been employed in pharmacology as potential novel antibacterial agents and prodrugs (Adams et al., 2002, Kimberly D. Grimes et al., 2008); some carbacylamidophosphates are effective pesticides (Barak et al., 2000). The ability of carbacylamidophosphates to form stable complexes both with transition and non-transition metals via their =P(O)N(H)C(O)- moiety has been investigated extensively by Amirkhanov et al., 1996, Trush et al., 2005, Ovchinnikov et al., 2001, Gholivand et al., 2006, Wenjun Zhang et al., 1992. This paper is devoted to the crystal structure of the sodium salt of 2,2,2-trichloro-N-(dimorpholin-4-yl-phosphoryl)acetamide (HL) NaL and the first fact of bridging coordination of CAPh ligand via carbonyl oxygen. Coordination compounds of 4f-metal ions with HL have been reported earlier (Ovchynnikov et al., 2000, Trush et al., 2002, Trush et al., 2003).

The molecular structure of the title compound is shown in Fig. 1. The structure is build up of [C₁₀H₁₈Cl₃N₃NaO₅P]n chains along [001]. The polymeric chain contains Na atoms, which are five-coordinated by three O atoms of 2 HL molecules and two O atoms of water. Each CAPh ligand links Na⁺ centers via its phosphoryl and carbonyl groups in a chelating manner. Oxygen atom of carbonyl group is a bridging atom between two sodium ions. The value of the trigonality index τ (τ = (β-α)/60, where α and β are the largest coordination angles) (Addison et al., 1984) is 0,049 for Na(1) [α = O(4)—Na(1)—O(1 W) = 140,69°, β = O(3)—Na(1)—O(4) = 143,63°]. It indicates that sodium (I) ion is in a distorted trigonal bipyramidal coordination geometry. One of the equatorial distances is significantly longer [Na(1)—O(1 W) = 3,022 Å] than all other Na—O distances, which are almost equivalent. The values of the O—Na—O angles also reveal the strong deviation of the sodium (I) atom environment from the ideal trigonal- bipyramidal geometry. The P=O and C=O distances in the chelate ring and P—N distances in the morpholine substituents of L^- in the sodium salt are longer than in the free ligand (i. e. uncoordinated) (Table 1). But the P—N_amide distance is shortened upon coordination, indicating the presence of π-conjugation in the coordinated anion. Carbonyl group oxygen forms two types of bonds with Na: intrachelating bond O—Na is some longer, than bond with other Na atom. The bridging water molecules are involved in hydrogen bonding interactions (Table 1). Intramolecular hydrogen bonds stabilize the two-dimensional structure of the title compound. They are oriented towards the neighboring oxygen atom O(2) of the morpholine rings. The other H atom of the water molecule makes a strong intermolecular H bond to O(3) of P=O group of neighboring L^- molecule. The intermolecular hydrogen bonds are arranged in inversion symmetric pairs that connect molecules along the c-axis leading to strongly hydrogen bonded strings of the molecules along that axis (Figure 2).

Related literature top

For the pharmacological and biological properties of carbacylamidophosphate (CAPh) derivatives, see: Barak et al. (2000); Grimes et al. (2008); Adams et al. (2002); For structural analogues of phosphorylated carbacylamides and their coordination properties, see: Amirkhanov et al. (1996); Rebrova et al. (1982); Gubina et al. (1999); Ovchinnikov et al. (2001); Gholivand et al. (2006); Trush et al. (2005); Zhang et al. (1992). For details of the synthesis, see: Kirsanov & Derkach (1956). For the synthesis of the 2,2,2-trichloro-N-(dimorpholin-4-yl-phosphoryl)acetamide (HL) ligand, see: Ovchynnikov et al. (1998). For coordination compounds of HL, see: Ovchynnikov et al. (2000); Trush et al. (2002, 2003). For the trigonality index τ, see: Addison et al. (1984).

Experimental top

The synthesis of HL was carried out according to the method described early (Ovchynnikov et al., 1998).

HL (0,38 g, 1 mmol) was dissolved in methanol (10 ml) and added to 10 ml of sodium methoxide (0,023 g, 1 mmol of Na in methanol). After 20 min the solution was evaporated and the residue was dissolved in water. The resulting clear solution was left at ambient temperature for crystallization in air. The crystals were separated by filtration after 48 h and dried in air. Yield: 95-98%. IR (KBr pellet, cm^-1): 1605 (s, CO), 1344 (Amide II), 1152 (s, PO).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A portion of polymeric chain of the title compound, showing the 30% probability displacement ellipsoids and atomic numbering [symmetry codes: ]. H atoms of L^- and Cl atoms of trychlormethyl groups have been omitted for clarity.
	Fig. 2. A schematic view of packing diagram from [Na(L)(H₂O)]n (projection along the y direction). H atoms and Cl atoms of trychlormethyl groups have been omitted for clarity.

catena-Poly[sodium-di-µ-aqua-sodium-bis[µ-2,2,2-trichloro-N- (dimorpholinophosphoryl)acetamide]] top

Crystal data top

[Na₂(C₁₀H₁₆Cl₃N₃O₄P)₂(H₂O)₂]	Z = 1
M_r = 841.17	F(000) = 432
Triclinic, P1	D_x = 1.557 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.522 (5) Å	Cell parameters from 2305 reflections
b = 10.329 (4) Å	θ = 2.9–32.1°
c = 12.451 (5) Å	µ = 0.65 mm⁻¹
α = 84.17 (4)°	T = 294 K
β = 80.89 (4)°	Block, colourless
γ = 70.16 (5)°	0.40 × 0.30 × 0.20 mm
V = 897.3 (8) Å³

Data collection top

Oxford Diffraction Xcalibur3 diffractometer	5137 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3339 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 16.1827 pixels mm^-1	θ_max = 30.0°, θ_min = 3.0°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −14→14
T_min = 0.782, T_max = 0.938	l = −17→17
10258 measured reflections

Refinement top

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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F²) = 0.121	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0695P)²] where P = (F_o² + 2F_c²)/3
5137 reflections	(Δ/σ)_max < 0.001
236 parameters	Δρ_max = 0.44 e Å⁻³
6 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Na₂(C₁₀H₁₆Cl₃N₃O₄P)₂(H₂O)₂]	γ = 70.16 (5)°
M_r = 841.17	V = 897.3 (8) Å³
Triclinic, P1	Z = 1
a = 7.522 (5) Å	Mo Kα radiation
b = 10.329 (4) Å	µ = 0.65 mm⁻¹
c = 12.451 (5) Å	T = 294 K
α = 84.17 (4)°	0.40 × 0.30 × 0.20 mm
β = 80.89 (4)°

Data collection top

Oxford Diffraction Xcalibur3 diffractometer	5137 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	3339 reflections with I > 2σ(I)
T_min = 0.782, T_max = 0.938	R_int = 0.027
10258 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	6 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 0.95	Δρ_max = 0.44 e Å⁻³
5137 reflections	Δρ_min = −0.55 e Å⁻³
236 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Na1	0.74853 (12)	−0.02122 (8)	0.49141 (6)	0.0462 (2)
P1	0.14168 (7)	0.19927 (5)	0.73292 (4)	0.03306 (13)
Cl1	0.7919 (6)	−0.0374 (6)	0.7663 (5)	0.0975 (19)	0.30
Cl2	0.5558 (14)	−0.1440 (9)	0.9126 (2)	0.082 (3)	0.30
Cl3	0.6925 (9)	−0.2632 (4)	0.7073 (5)	0.109 (2)	0.30
Cl1A	0.8282 (3)	−0.0794 (3)	0.7362 (2)	0.1334 (12)	0.70
Cl2A	0.5706 (5)	−0.1301 (4)	0.91551 (8)	0.0708 (8)	0.70
Cl3A	0.6346 (6)	−0.26558 (18)	0.7220 (3)	0.1413 (14)	0.70
N1	−0.0076 (2)	0.25733 (16)	0.84197 (13)	0.0387 (4)
N2	0.2136 (2)	0.33001 (16)	0.68794 (12)	0.0376 (3)
N3	0.3105 (2)	0.07308 (16)	0.78548 (13)	0.0398 (4)
O1	−0.2764 (2)	0.36756 (19)	1.02222 (14)	0.0712 (5)
O2	0.3238 (3)	0.55916 (17)	0.61132 (14)	0.0605 (4)
O3	0.05740 (19)	0.16343 (14)	0.64384 (11)	0.0436 (3)
O4	0.4863 (2)	0.00857 (16)	0.61885 (11)	0.0492 (4)
C1	−0.0371 (3)	0.1708 (2)	0.93747 (19)	0.0533 (5)
H1B	0.0821	0.0987	0.9481	0.064*
H1A	−0.1285	0.1274	0.9268	0.064*
C2	−0.1092 (4)	0.2545 (3)	1.03586 (19)	0.0689 (7)
H2A	−0.1360	0.1962	1.0980	0.083*
H2B	−0.0108	0.2885	1.0511	0.083*
C3	−0.2430 (4)	0.4527 (2)	0.9306 (2)	0.0621 (6)
H3A	−0.1457	0.4902	0.9421	0.074*
H3B	−0.3590	0.5292	0.9222	0.074*
C4	−0.1799 (3)	0.3747 (2)	0.82922 (18)	0.0517 (5)
H4B	−0.2802	0.3423	0.8146	0.062*
H4A	−0.1544	0.4347	0.7680	0.062*
C5	0.3079 (4)	0.3877 (2)	0.75538 (18)	0.0520 (5)
H5B	0.4445	0.3403	0.7443	0.062*
H5A	0.2618	0.3753	0.8317	0.062*
C6	0.2665 (4)	0.5365 (3)	0.7248 (2)	0.0583 (6)
H6A	0.1309	0.5843	0.7421	0.070*
H6B	0.3332	0.5744	0.7671	0.070*
C7	0.2333 (4)	0.5012 (2)	0.54594 (19)	0.0577 (6)
H7A	0.2777	0.5158	0.4696	0.069*
H7B	0.0966	0.5477	0.5578	0.069*
C8	0.2748 (3)	0.3510 (2)	0.57246 (16)	0.0462 (5)
H8B	0.2074	0.3148	0.5293	0.055*
H8A	0.4103	0.3027	0.5556	0.055*
C9	0.4531 (3)	0.00130 (18)	0.71992 (15)	0.0344 (4)
C10	0.61717 (19)	−0.11305 (14)	0.77559 (8)	0.0466 (5)
O1W	0.8336 (3)	0.16719 (17)	0.49163 (14)	0.0647 (5)
H1WA	0.8908	0.1732	0.5556	0.097*
H1WB	0.7821	0.2673	0.4784	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0504 (5)	0.0472 (5)	0.0453 (4)	−0.0219 (4)	0.0012 (4)	−0.0133 (4)
P1	0.0316 (2)	0.0281 (2)	0.0357 (2)	−0.00463 (17)	−0.00432 (19)	−0.00264 (18)
Cl1	0.064 (3)	0.116 (3)	0.139 (5)	−0.054 (3)	−0.054 (3)	0.027 (3)
Cl2	0.101 (5)	0.052 (2)	0.050 (3)	0.014 (2)	0.008 (3)	0.025 (2)
Cl3	0.134 (3)	0.065 (3)	0.057 (2)	0.067 (2)	−0.013 (2)	−0.0271 (19)
Cl1A	0.0365 (6)	0.226 (3)	0.1052 (14)	−0.0258 (11)	−0.0134 (7)	0.0845 (18)
Cl2A	0.0624 (10)	0.0851 (18)	0.0385 (10)	0.0109 (10)	−0.0100 (8)	−0.0020 (9)
Cl3A	0.274 (4)	0.0300 (8)	0.0826 (14)	−0.0019 (12)	−0.0180 (19)	−0.0110 (7)
N1	0.0328 (8)	0.0308 (8)	0.0405 (8)	0.0016 (6)	0.0014 (7)	0.0008 (7)
N2	0.0426 (8)	0.0367 (8)	0.0346 (8)	−0.0143 (7)	−0.0067 (7)	−0.0013 (7)
N3	0.0375 (8)	0.0341 (8)	0.0377 (8)	0.0006 (6)	−0.0022 (7)	−0.0033 (7)
O1	0.0557 (10)	0.0682 (11)	0.0529 (10)	0.0173 (8)	0.0118 (8)	0.0019 (9)
O2	0.0806 (12)	0.0514 (9)	0.0615 (10)	−0.0379 (9)	−0.0111 (9)	0.0026 (8)
O3	0.0414 (7)	0.0408 (7)	0.0504 (8)	−0.0124 (6)	−0.0115 (7)	−0.0057 (6)
O4	0.0415 (7)	0.0600 (9)	0.0353 (7)	−0.0027 (7)	−0.0040 (6)	−0.0034 (6)
C1	0.0492 (12)	0.0393 (11)	0.0546 (13)	−0.0023 (9)	0.0071 (11)	0.0079 (10)
C2	0.0613 (15)	0.0683 (17)	0.0442 (12)	0.0153 (12)	0.0022 (12)	0.0038 (12)
C3	0.0486 (12)	0.0448 (13)	0.0688 (16)	0.0101 (10)	0.0054 (12)	−0.0041 (11)
C4	0.0375 (10)	0.0479 (12)	0.0509 (12)	0.0067 (9)	−0.0033 (9)	0.0057 (10)
C5	0.0600 (13)	0.0602 (14)	0.0483 (12)	−0.0318 (12)	−0.0184 (11)	0.0008 (10)
C6	0.0734 (16)	0.0563 (14)	0.0560 (13)	−0.0320 (13)	−0.0115 (13)	−0.0104 (11)
C7	0.0838 (17)	0.0493 (13)	0.0477 (12)	−0.0317 (13)	−0.0145 (12)	0.0066 (10)
C8	0.0576 (12)	0.0406 (11)	0.0377 (10)	−0.0158 (10)	0.0021 (9)	−0.0047 (9)
C9	0.0346 (9)	0.0284 (8)	0.0369 (9)	−0.0060 (7)	−0.0045 (8)	−0.0019 (7)
C10	0.0432 (10)	0.0420 (11)	0.0400 (10)	0.0017 (9)	−0.0003 (9)	0.0005 (9)
O1W	0.0899 (12)	0.0424 (9)	0.0748 (11)	−0.0292 (9)	−0.0365 (10)	0.0044 (8)

Geometric parameters (Å, º) top

Na1—O1W	2.2458 (19)	O3—Na1ⁱ	2.322 (2)
Na1—O4	2.280 (2)	O4—C9	1.243 (2)
Na1—O3ⁱ	2.322 (2)	O4—Na1ⁱ	2.366 (2)
Na1—O4ⁱ	2.366 (2)	C1—C2	1.493 (3)
Na1—Cl1A	3.158 (3)	C1—H1B	0.9700
Na1—P1ⁱ	3.3388 (19)	C1—H1A	0.9700
P1—O3	1.4949 (15)	C2—H2A	0.9700
P1—O3	1.4949 (15)	C2—H2B	0.9700
P1—N2	1.6358 (18)	C3—C4	1.492 (4)
P1—N1	1.6401 (19)	C3—H3A	0.9700
P1—N3	1.645 (2)	C3—H3B	0.9700
P1—Na1ⁱ	3.3388 (19)	C4—H4B	0.9700
Cl1—C10	1.7264 (14)	C4—H4A	0.9700
Cl2—C10	1.7219 (13)	C5—C6	1.483 (3)
Cl3—C10	1.7222 (14)	C5—H5B	0.9700
Cl1A—C10	1.7246 (15)	C5—H5A	0.9700
Cl2A—C10	1.7248 (12)	C6—H6A	0.9700
Cl3A—C10	1.7290 (13)	C6—H6B	0.9700
N1—C1	1.448 (3)	C7—C8	1.488 (3)
N1—C4	1.461 (3)	C7—H7A	0.9700
N2—C8	1.456 (2)	C7—H7B	0.9700
N2—C5	1.463 (3)	C8—H8B	0.9700
N3—C9	1.293 (3)	C8—H8A	0.9700
O1—C3	1.412 (3)	C9—C10	1.586 (3)
O1—C2	1.416 (3)	O1W—H1WA	0.9800
O2—C7	1.427 (3)	O1W—H1WB	0.9800
O2—C6	1.430 (3)

O1W—Na1—O4	106.11 (9)	O1—C2—H2B	109.2
O1W—Na1—O3ⁱ	110.04 (8)	C1—C2—H2B	109.2
O4—Na1—O3ⁱ	143.65 (7)	H2A—C2—H2B	107.9
O1W—Na1—O4ⁱ	117.21 (8)	O1—C3—C4	111.4 (2)
O4—Na1—O4ⁱ	78.92 (7)	O1—C3—H3A	109.4
O3ⁱ—Na1—O4ⁱ	81.39 (7)	C4—C3—H3A	109.4
O1W—Na1—Cl1A	86.78 (8)	O1—C3—H3B	109.4
O4—Na1—Cl1A	64.22 (7)	C4—C3—H3B	109.4
O3ⁱ—Na1—Cl1A	121.01 (9)	H3A—C3—H3B	108.0
O4ⁱ—Na1—Cl1A	140.84 (6)	N1—C4—C3	109.77 (19)
O1W—Na1—P1ⁱ	119.98 (7)	N1—C4—H4B	109.7
O4—Na1—P1ⁱ	127.30 (6)	C3—C4—H4B	109.7
O3ⁱ—Na1—P1ⁱ	22.70 (4)	N1—C4—H4A	109.7
O4ⁱ—Na1—P1ⁱ	58.77 (6)	C3—C4—H4A	109.7
Cl1A—Na1—P1ⁱ	137.07 (7)	H4B—C4—H4A	108.2
O1W—Na1—Na1ⁱ	118.55 (8)	N2—C5—C6	108.99 (19)
O4—Na1—Na1ⁱ	40.33 (5)	N2—C5—H5B	109.9
O3ⁱ—Na1—Na1ⁱ	114.40 (6)	C6—C5—H5B	109.9
O4ⁱ—Na1—Na1ⁱ	38.58 (5)	N2—C5—H5A	109.9
Cl1A—Na1—Na1ⁱ	103.59 (6)	C6—C5—H5A	109.9
P1ⁱ—Na1—Na1ⁱ	92.48 (5)	H5B—C5—H5A	108.3
O1W—Na1—Na1ⁱⁱ	48.58 (7)	O2—C6—C5	111.5 (2)
O4—Na1—Na1ⁱⁱ	130.58 (6)	O2—C6—H6A	109.3
O3ⁱ—Na1—Na1ⁱⁱ	78.91 (6)	C5—C6—H6A	109.3
O4ⁱ—Na1—Na1ⁱⁱ	147.34 (6)	O2—C6—H6B	109.3
Cl1A—Na1—Na1ⁱⁱ	71.78 (5)	C5—C6—H6B	109.3
P1ⁱ—Na1—Na1ⁱⁱ	100.05 (5)	H6A—C6—H6B	108.0
Na1ⁱ—Na1—Na1ⁱⁱ	165.63 (5)	O2—C7—C8	111.4 (2)
O3—P1—N2	107.86 (9)	O2—C7—H7A	109.3
O3—P1—N2	107.86 (9)	C8—C7—H7A	109.3
O3—P1—N1	115.65 (9)	O2—C7—H7B	109.3
O3—P1—N1	115.65 (9)	C8—C7—H7B	109.3
N2—P1—N1	102.81 (9)	H7A—C7—H7B	108.0
O3—P1—N3	116.42 (9)	N2—C8—C7	108.85 (18)
O3—P1—N3	116.42 (9)	N2—C8—H8B	109.9
N2—P1—N3	111.58 (10)	C7—C8—H8B	109.9
N1—P1—N3	101.70 (9)	N2—C8—H8A	109.9
N2—P1—Na1ⁱ	100.79 (7)	C7—C8—H8A	109.9
N1—P1—Na1ⁱ	149.19 (7)	H8B—C8—H8A	108.3
N3—P1—Na1ⁱ	87.59 (8)	O4—C9—N3	130.61 (18)
C10—Cl1A—Na1	91.55 (11)	O4—C9—C10	113.42 (15)
C1—N1—C4	111.08 (17)	N3—C9—C10	115.95 (15)
C1—N1—P1	123.56 (14)	C9—C10—Cl2	113.7 (3)
C4—N1—P1	118.63 (14)	C9—C10—Cl3	110.5 (2)
C8—N2—C5	111.34 (16)	Cl2—C10—Cl3	110.9 (4)
C8—N2—P1	120.92 (13)	C9—C10—Cl1A	108.77 (14)
C5—N2—P1	121.27 (14)	Cl2—C10—Cl1A	117.4 (4)
C9—N3—P1	118.23 (14)	Cl3—C10—Cl1A	93.9 (3)
C3—O1—C2	110.45 (18)	C9—C10—Cl2A	114.42 (16)
C7—O2—C6	111.22 (16)	Cl3—C10—Cl2A	116.2 (3)
P1—O3—Na1ⁱ	120.47 (9)	Cl1A—C10—Cl2A	111.12 (18)
C9—O4—Na1	136.68 (13)	C9—C10—Cl1	102.9 (2)
C9—O4—Na1ⁱ	121.40 (13)	Cl2—C10—Cl1	106.0 (5)
Na1—O4—Na1ⁱ	101.08 (7)	Cl3—C10—Cl1	112.7 (3)
N1—C1—C2	110.33 (19)	Cl2A—C10—Cl1	98.9 (3)
N1—C1—H1B	109.6	C9—C10—Cl3A	104.82 (15)
C2—C1—H1B	109.6	Cl2—C10—Cl3A	102.2 (4)
N1—C1—H1A	109.6	Cl1A—C10—Cl3A	109.0 (2)
C2—C1—H1A	109.6	Cl2A—C10—Cl3A	108.5 (2)
H1B—C1—H1A	108.1	Cl1—C10—Cl3A	127.7 (3)
O1—C2—C1	112.3 (2)	Na1—O1W—H1WA	115.1
O1—C2—H2A	109.2	Na1—O1W—H1WB	139.9
C1—C2—H2A	109.2	H1WA—O1W—H1WB	94.1

O1W—Na1—Cl1A—C10	133.78 (14)	O1W—Na1—O4—Na1ⁱ	115.37 (8)
O4—Na1—Cl1A—C10	24.16 (11)	O3ⁱ—Na1—O4—Na1ⁱ	−58.44 (12)
O3ⁱ—Na1—Cl1A—C10	−114.71 (13)	O4ⁱ—Na1—O4—Na1ⁱ	0.0
O4ⁱ—Na1—Cl1A—C10	2.8 (2)	Cl1A—Na1—O4—Na1ⁱ	−166.44 (9)
P1ⁱ—Na1—Cl1A—C10	−93.81 (14)	P1ⁱ—Na1—O4—Na1ⁱ	−35.57 (8)
Na1ⁱ—Na1—Cl1A—C10	15.17 (14)	Na1ⁱⁱ—Na1—O4—Na1ⁱ	164.12 (7)
Na1ⁱⁱ—Na1—Cl1A—C10	−178.99 (14)	C4—N1—C1—C2	−53.9 (3)
O3—P1—N1—C1	94.71 (18)	P1—N1—C1—C2	155.41 (17)
O3—P1—N1—C1	94.71 (18)	C3—O1—C2—C1	−57.4 (3)
N2—P1—N1—C1	−148.03 (17)	N1—C1—C2—O1	55.1 (3)
N3—P1—N1—C1	−32.41 (19)	C2—O1—C3—C4	58.7 (3)
Na1ⁱ—P1—N1—C1	72.9 (2)	C1—N1—C4—C3	55.3 (3)
O3—P1—N1—C4	−53.94 (18)	P1—N1—C4—C3	−152.41 (17)
O3—P1—N1—C4	−53.94 (18)	O1—C3—C4—N1	−57.7 (3)
N2—P1—N1—C4	63.32 (17)	C8—N2—C5—C6	57.6 (3)
N3—P1—N1—C4	178.94 (15)	P1—N2—C5—C6	−150.46 (17)
Na1ⁱ—P1—N1—C4	−75.8 (2)	C7—O2—C6—C5	57.2 (3)
O3—P1—N2—C8	−29.02 (18)	N2—C5—C6—O2	−56.6 (3)
O3—P1—N2—C8	−29.02 (18)	C6—O2—C7—C8	−57.4 (3)
N1—P1—N2—C8	−151.68 (16)	C5—N2—C8—C7	−57.7 (2)
N3—P1—N2—C8	100.04 (17)	P1—N2—C8—C7	150.24 (17)
Na1ⁱ—P1—N2—C8	8.36 (16)	O2—C7—C8—N2	57.1 (3)
O3—P1—N2—C5	−178.34 (16)	Na1—O4—C9—N3	144.80 (18)
O3—P1—N2—C5	−178.34 (16)	Na1ⁱ—O4—C9—N3	−47.9 (3)
N1—P1—N2—C5	59.00 (19)	Na1—O4—C9—C10	−33.5 (3)
N3—P1—N2—C5	−49.28 (19)	Na1ⁱ—O4—C9—C10	133.83 (12)
Na1ⁱ—P1—N2—C5	−140.96 (16)	P1—N3—C9—O4	−1.7 (3)
O3—P1—N3—C9	52.00 (18)	P1—N3—C9—C10	176.53 (10)
O3—P1—N3—C9	52.00 (18)	O4—C9—C10—Cl2	−169.7 (4)
N2—P1—N3—C9	−72.38 (17)	N3—C9—C10—Cl2	11.8 (4)
N1—P1—N3—C9	178.63 (15)	O4—C9—C10—Cl3	−44.2 (3)
Na1ⁱ—P1—N3—C9	28.27 (15)	N3—C9—C10—Cl3	137.3 (3)
N2—P1—O3—O3	0.00 (17)	O4—C9—C10—Cl1A	57.5 (2)
N1—P1—O3—O3	0.00 (13)	N3—C9—C10—Cl1A	−121.00 (19)
N3—P1—O3—O3	0.00 (14)	O4—C9—C10—Cl2A	−177.6 (2)
Na1ⁱ—P1—O3—O3	0.00 (14)	N3—C9—C10—Cl2A	3.9 (3)
O3—P1—O3—Na1ⁱ	0 (50)	O4—C9—C10—Cl1	76.3 (3)
N2—P1—O3—Na1ⁱ	84.15 (12)	N3—C9—C10—Cl1	−102.3 (3)
N1—P1—O3—Na1ⁱ	−161.45 (8)	O4—C9—C10—Cl3A	−58.9 (2)
N3—P1—O3—Na1ⁱ	−42.12 (12)	N3—C9—C10—Cl3A	122.6 (2)
O1W—Na1—O4—C9	−75.7 (2)	Na1—Cl1A—C10—C9	−44.71 (14)
O3ⁱ—Na1—O4—C9	110.5 (2)	Na1—Cl1A—C10—Cl2	−175.6 (3)
O4ⁱ—Na1—O4—C9	169.0 (2)	Na1—Cl1A—C10—Cl3	68.4 (2)
Cl1A—Na1—O4—C9	2.54 (19)	Na1—Cl1A—C10—Cl2A	−171.53 (16)
P1ⁱ—Na1—O4—C9	133.41 (18)	Na1—Cl1A—C10—Cl1	−119.3 (9)
Na1ⁱ—Na1—O4—C9	169.0 (2)	Na1—Cl1A—C10—Cl3A	69.00 (16)
Na1ⁱⁱ—Na1—O4—C9	−26.9 (2)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O1ⁱⁱⁱ	0.97	2.59	3.443 (4)	147
O1W—H1WA···O3^iv	0.98	1.77	2.716 (3)	163
O1W—H1WB···O2^v	0.98	2.00	2.917 (3)	155

Symmetry codes: (iii) −x−1, −y+1, −z+2; (iv) x+1, y, z; (v) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Na₂(C₁₀H₁₆Cl₃N₃O₄P)₂(H₂O)₂]
M_r	841.17
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.522 (5), 10.329 (4), 12.451 (5)
α, β, γ (°)	84.17 (4), 80.89 (4), 70.16 (5)
V (Å³)	897.3 (8)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur3 diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.782, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	10258, 5137, 3339
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.121, 0.95
No. of reflections	5137
No. of parameters	236
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.55

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXTL (Sheldrick, 2008), XP in SHELXTL Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O1ⁱ	0.97	2.59	3.443 (4)	147.0
O1W—H1WA···O3ⁱⁱ	0.98	1.77	2.716 (3)	163
O1W—H1WB···O2ⁱⁱⁱ	0.98	2.00	2.917 (3)	155

Symmetry codes: (i) −x−1, −y+1, −z+2; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1.

References

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages m426-m427

doi:10.1107/S1600536810009670

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

catena-Poly[sodium-di-μ-aqua-sodium-bis­[μ-2,2,2-tri­chloro-N-(di­morpholino­phosphoryl)acetamide]]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

catena-Poly[sodium-di-μ-aqua-sodium-bis[μ-2,2,2-trichloro-N-(dimorpholinophosphoryl)acetamide]]