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

The title compound, [Na(2)(C(10)H(16)Cl(3)N(3)O(4)P)(2)(H(2)O)(2)](n), can be considered as a two-dimensional coordination polymer in which one-dimensional chains are connected to each other by inter-molecular C-H⋯O hydrogen bonds involving the water mol-ecules. 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-(dimorpholino-phosphor-yl)acetamide (CAPh) ligand. A bridging coordination of the CAPh ligand via the carbonyl O atom is observed for the first time. The bridging water mol-ecules form inter-molecular O-H⋯O hydrogen bonds with the O atoms of the morpholine rings and the phosphoryl groups of neighboring CAPh mol-ecules.

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 = 841.17

Triclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.121

S = 0.95

5137 reflections

236 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.55 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); 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.

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

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

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

[Na2(C10H16Cl3N3O4P)2(H2O)2]	Z = 1
Mr = 841.17	F(000) = 432
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0695P)2] where P = (Fo2 + 2Fc2)/3
5137 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.44 e Å−3
6 restraints	Δρmin = −0.55 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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···O3iv	0.98	1.77	2.716 (3)	163
O1W—H1WB···O2v	0.98	2.00	2.917 (3)	155

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) ; (ii) ; (iii) .