Poly[μ₂-aqua-μ₄-(2-{3-[(6-chloro-pyridin-3-yl)meth-yl]-2-oxoimidazolidin-1-yl}acetato)-sodium].

In the title compound, [Na(C₁₁H₁₁ClN₃O₃)(H₂O)](n), there are two independent Na(I) ions, one of which lies on an inversion center and is coordinated in a slightly distorted octa-hedral environment. The other Na(I) ion lies on a twofold rotation axis and is cooordinated in a slightly distorted trigonal-bipyramidal coordination environment. In the organic ligand, the imidazolidine ring adopts a half-chair conformation. The Na(I) ions bridge organic ligands and water mol-ecules, forming a two-dimensional structure parallel to (100). There are inter-molecular O-H⋯O and weak C-H⋯O hydrogen bonds within the two-dimensional structure.

Related literature

For background to the insecticidal applications of imidacloprid {systematic name: N-[1-[(6-chloro-3-pyrid­yl)meth­yl]-4,5-dihydro­imidazol-2-yl]nitramide}, see: Legocki & Polec (2008 ▶); Kovganko & Kashkan (2004 ▶); Zhao et al. (2009 ▶); Tanner et al. (2010 ▶); Xu et al. (2010 ▶). For ring conformations, see: Duax & Norton (1975 ▶). For related structures, see: Kapoor et al. (2011 ▶, 2012 ▶); Kant et al. (2012 ▶).

Experimental

Crystal data

[Na(C11H11ClN3O3)(H2O)]

M = 309.68

Monoclinic,

a = 45.655 (2) Å

b = 4.9113 (2) Å

c = 12.5205 (7) Å

β = 102.184 (5)°

V = 2744.2 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.836, T max = 1.000

9498 measured reflections

2678 independent reflections

1909 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.112

S = 1.02

2678 reflections

191 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.46 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812025007/lh5481sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025007/lh5481Isup2.hkl

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

[Na(C11H11ClN3O3)(H2O)]	F(000) = 1280
Mr = 309.68	Dx = 1.499 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5286 reflections
a = 45.655 (2) Å	θ = 3.6–29.0°
b = 4.9113 (2) Å	µ = 0.33 mm−1
c = 12.5205 (7) Å	T = 293 K
β = 102.184 (5)°	Block, white
V = 2744.2 (2) Å3	0.3 × 0.2 × 0.1 mm
Z = 8

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2678 independent reflections
Radiation source: fine-focus sealed tube	1909 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.6°
ω scan	h = −56→52
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→5
Tmin = 0.836, Tmax = 1.000	l = −15→15
9498 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: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0459P)2 + 2.523P] where P = (Fo2 + 2Fc2)/3
2678 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Na1	1.0000	1.0000	0.0000	0.0267 (3)
Na2	1.0000	1.0028 (2)	0.2500	0.0286 (3)
Cl1	0.76939 (2)	0.7478 (2)	0.18991 (10)	0.0963 (4)
N1	0.81725 (5)	0.4509 (6)	0.2281 (2)	0.0652 (7)
C2	0.81005 (7)	0.2440 (7)	0.0194 (3)	0.0685 (9)
H2	0.8072	0.1756	−0.0513	0.082*
C3	0.83467 (6)	0.1665 (5)	0.0972 (2)	0.0447 (7)
C4	0.83683 (7)	0.2781 (6)	0.1992 (3)	0.0570 (8)
H4	0.8534	0.2292	0.2529	0.068*
C5	0.78956 (7)	0.4245 (8)	0.0471 (3)	0.0769 (11)
H5	0.7728	0.4802	−0.0043	0.092*
C6	0.79453 (7)	0.5174 (7)	0.1510 (3)	0.0614 (8)
C7	0.85914 (6)	−0.0155 (5)	0.0735 (2)	0.0491 (7)
H7A	0.8676	−0.1189	0.1387	0.059*
H7B	0.8505	−0.1439	0.0167	0.059*
N8	0.88292 (4)	0.1344 (4)	0.03879 (16)	0.0377 (5)
C9	0.87821 (7)	0.2620 (6)	−0.0683 (2)	0.0549 (8)
H9A	0.8602	0.3723	−0.0825	0.066*
H9B	0.8770	0.1275	−0.1257	0.066*
C10	0.90605 (6)	0.4362 (6)	−0.0581 (2)	0.0512 (7)
H10A	0.9219	0.3394	−0.0829	0.061*
H10B	0.9018	0.6046	−0.0989	0.061*
N11	0.91385 (4)	0.4864 (4)	0.05842 (16)	0.0331 (5)
C12	0.90251 (5)	0.2884 (5)	0.11303 (19)	0.0299 (5)
O12	0.90778 (4)	0.2517 (4)	0.21182 (13)	0.0437 (5)
C13	0.94038 (5)	0.6403 (5)	0.1062 (2)	0.0360 (6)
H13A	0.9397	0.6836	0.1812	0.043*
H13B	0.9401	0.8108	0.0668	0.043*
C14	0.96972 (5)	0.4954 (4)	0.10520 (16)	0.0228 (5)
O15	0.99295 (3)	0.6404 (3)	0.12325 (12)	0.0268 (4)
O16	0.96893 (3)	0.2446 (3)	0.09003 (13)	0.0302 (4)
O1W	1.03482 (4)	1.2101 (4)	0.15005 (15)	0.0364 (4)
H1W	1.0512 (7)	1.220 (6)	0.189 (3)	0.055 (9)*
H2W	1.0263 (8)	1.361 (8)	0.152 (3)	0.082 (12)*

	U11	U22	U33	U12	U13	U23
Na1	0.0343 (7)	0.0252 (6)	0.0226 (6)	−0.0001 (5)	0.0104 (5)	−0.0014 (5)
Na2	0.0387 (7)	0.0243 (6)	0.0236 (6)	0.000	0.0084 (5)	0.000
Cl1	0.0693 (6)	0.1034 (8)	0.1248 (9)	0.0315 (5)	0.0398 (6)	0.0245 (6)
N1	0.0462 (15)	0.0806 (19)	0.0682 (18)	0.0095 (14)	0.0111 (13)	0.0045 (15)
C2	0.0438 (18)	0.095 (3)	0.059 (2)	−0.0028 (18)	−0.0058 (15)	−0.0005 (19)
C3	0.0307 (13)	0.0456 (15)	0.0556 (18)	−0.0117 (12)	0.0042 (12)	0.0062 (13)
C4	0.0397 (16)	0.073 (2)	0.0546 (19)	0.0058 (15)	0.0004 (13)	0.0096 (16)
C5	0.0401 (18)	0.104 (3)	0.079 (3)	0.0158 (18)	−0.0045 (17)	0.019 (2)
C6	0.0423 (17)	0.067 (2)	0.078 (2)	0.0010 (15)	0.0184 (16)	0.0143 (18)
C7	0.0412 (15)	0.0387 (14)	0.0650 (19)	−0.0123 (13)	0.0060 (13)	−0.0015 (14)
N8	0.0363 (11)	0.0375 (11)	0.0369 (12)	−0.0057 (10)	0.0024 (9)	−0.0023 (9)
C9	0.0507 (17)	0.074 (2)	0.0349 (16)	−0.0085 (15)	−0.0032 (13)	−0.0032 (14)
C10	0.0439 (15)	0.074 (2)	0.0327 (15)	−0.0043 (14)	0.0015 (12)	0.0151 (14)
N11	0.0278 (10)	0.0322 (10)	0.0386 (11)	−0.0006 (9)	0.0057 (8)	0.0036 (9)
C12	0.0242 (11)	0.0327 (12)	0.0327 (14)	0.0049 (10)	0.0057 (10)	−0.0007 (10)
O12	0.0328 (9)	0.0672 (12)	0.0308 (10)	−0.0053 (8)	0.0057 (7)	0.0033 (9)
C13	0.0331 (13)	0.0251 (11)	0.0517 (16)	0.0000 (10)	0.0133 (11)	−0.0013 (11)
C14	0.0302 (11)	0.0213 (10)	0.0173 (10)	0.0011 (10)	0.0063 (9)	0.0016 (9)
O15	0.0288 (8)	0.0230 (7)	0.0283 (8)	−0.0029 (7)	0.0056 (6)	−0.0017 (6)
O16	0.0329 (9)	0.0182 (7)	0.0410 (9)	−0.0002 (6)	0.0116 (7)	−0.0023 (6)
O1W	0.0315 (10)	0.0405 (11)	0.0347 (10)	−0.0025 (9)	0.0011 (8)	−0.0037 (8)

Na1—O16i	2.3239 (14)	C5—C6	1.351 (5)
Na1—O16ii	2.3239 (14)	C5—H5	0.9300
Na1—O15iii	2.4112 (14)	C7—N8	1.452 (3)
Na1—O15	2.4112 (14)	C7—H7A	0.9700
Na1—O1Wiii	2.4208 (18)	C7—H7B	0.9700
Na1—O1W	2.4208 (18)	N8—C12	1.373 (3)
Na1—Na2iii	3.1302 (2)	N8—C9	1.454 (3)
Na1—Na2	3.1302 (2)	C9—C10	1.515 (4)
Na2—O15	2.3611 (16)	C9—H9A	0.9700
Na2—O15iv	2.3611 (16)	C9—H9B	0.9700
Na2—O1W	2.4432 (18)	C10—N11	1.448 (3)
Na2—O1Wiv	2.4432 (18)	C10—H10A	0.9700
Na2—O16v	2.4969 (16)	C10—H10B	0.9700
Na2—O16ii	2.4968 (16)	N11—C12	1.353 (3)
Na2—Na1iv	3.1302 (2)	N11—C13	1.446 (3)
Na2—H2W	2.58 (3)	C12—O12	1.223 (3)
Cl1—C6	1.753 (3)	C13—C14	1.519 (3)
N1—C6	1.301 (4)	C13—H13A	0.9700
N1—C4	1.336 (4)	C13—H13B	0.9700
C2—C3	1.377 (4)	C14—O16	1.246 (2)
C2—C5	1.385 (5)	C14—O15	1.257 (2)
C2—H2	0.9300	O16—Na1vi	2.3239 (14)
C3—C4	1.374 (4)	O16—Na2vi	2.4968 (16)
C3—C7	1.509 (4)	O1W—H1W	0.81 (3)
C4—H4	0.9300	O1W—H2W	0.84 (4)
O16i—Na1—O16ii	180.00 (5)	C6—N1—C4	115.7 (3)
O16i—Na1—O15iii	83.72 (5)	C3—C2—C5	119.6 (3)
O16ii—Na1—O15iii	96.28 (5)	C3—C2—H2	120.2
O16i—Na1—O15	96.28 (5)	C5—C2—H2	120.2
O16ii—Na1—O15	83.72 (5)	C4—C3—C2	115.8 (3)
O15iii—Na1—O15	180.00 (7)	C4—C3—C7	120.6 (2)
O16i—Na1—O1Wiii	76.78 (6)	C2—C3—C7	123.5 (3)
O16ii—Na1—O1Wiii	103.22 (6)	N1—C4—C3	125.7 (3)
O15iii—Na1—O1Wiii	88.29 (6)	N1—C4—H4	117.1
O15—Na1—O1Wiii	91.71 (6)	C3—C4—H4	117.1
O16i—Na1—O1W	103.22 (6)	C6—C5—C2	118.2 (3)
O16ii—Na1—O1W	76.78 (6)	C6—C5—H5	120.9
O15iii—Na1—O1W	91.71 (6)	C2—C5—H5	120.9
O15—Na1—O1W	88.29 (6)	N1—C6—C5	125.1 (3)
O1Wiii—Na1—O1W	180.00 (8)	N1—C6—Cl1	115.0 (3)
O16i—Na1—Na2iii	51.96 (4)	C5—C6—Cl1	119.9 (3)
O16ii—Na1—Na2iii	128.04 (4)	N8—C7—C3	112.9 (2)
O15iii—Na1—Na2iii	48.32 (4)	N8—C7—H7A	109.0
O15—Na1—Na2iii	131.68 (4)	C3—C7—H7A	109.0
O1Wiii—Na1—Na2iii	50.26 (4)	N8—C7—H7B	109.0
O1W—Na1—Na2iii	129.74 (4)	C3—C7—H7B	109.0
O16i—Na1—Na2	128.04 (4)	H7A—C7—H7B	107.8
O16ii—Na1—Na2	51.96 (4)	C12—N8—C7	119.9 (2)
O15iii—Na1—Na2	131.68 (4)	C12—N8—C9	109.6 (2)
O15—Na1—Na2	48.32 (4)	C7—N8—C9	121.3 (2)
O1Wiii—Na1—Na2	129.74 (4)	N8—C9—C10	102.0 (2)
O1W—Na1—Na2	50.26 (4)	N8—C9—H9A	111.4
Na2iii—Na1—Na2	180.00 (4)	C10—C9—H9A	111.4
O15—Na2—O15iv	82.15 (8)	N8—C9—H9B	111.4
O15—Na2—O1W	88.91 (5)	C10—C9—H9B	111.4
O15iv—Na2—O1W	130.33 (6)	H9A—C9—H9B	109.2
O15—Na2—O1Wiv	130.33 (6)	N11—C10—C9	101.8 (2)
O15iv—Na2—O1Wiv	88.91 (6)	N11—C10—H10A	111.4
O1W—Na2—O1Wiv	130.75 (10)	C9—C10—H10A	111.4
O15—Na2—O16v	150.63 (6)	N11—C10—H10B	111.4
O15iv—Na2—O16v	81.11 (5)	C9—C10—H10B	111.4
O1W—Na2—O16v	83.79 (6)	H10A—C10—H10B	109.3
O1Wiv—Na2—O16v	73.25 (6)	C12—N11—C13	122.9 (2)
O15—Na2—O16ii	81.11 (5)	C12—N11—C10	110.4 (2)
O15iv—Na2—O16ii	150.63 (6)	C13—N11—C10	120.80 (19)
O1W—Na2—O16ii	73.25 (6)	O12—C12—N11	127.1 (2)
O1Wiv—Na2—O16ii	83.79 (6)	O12—C12—N8	124.4 (2)
O16v—Na2—O16ii	123.21 (8)	N11—C12—N8	108.5 (2)
O15—Na2—Na1iv	129.79 (5)	N11—C13—C14	114.54 (18)
O15iv—Na2—Na1iv	49.71 (3)	N11—C13—H13A	108.6
O1W—Na2—Na1iv	130.64 (5)	C14—C13—H13A	108.6
O1Wiv—Na2—Na1iv	49.63 (4)	N11—C13—H13B	108.6
O16v—Na2—Na1iv	47.14 (3)	C14—C13—H13B	108.6
O16ii—Na2—Na1iv	133.19 (4)	H13A—C13—H13B	107.6
O15—Na2—Na1	49.71 (3)	O16—C14—O15	125.69 (19)
O15iv—Na2—Na1	129.79 (5)	O16—C14—C13	117.84 (18)
O1W—Na2—Na1	49.63 (4)	O15—C14—C13	116.43 (18)
O1Wiv—Na2—Na1	130.65 (5)	C14—O15—Na2	122.53 (12)
O16v—Na2—Na1	133.19 (4)	C14—O15—Na1	121.41 (12)
O16ii—Na2—Na1	47.14 (3)	Na2—O15—Na1	81.97 (5)
Na1iv—Na2—Na1	179.49 (4)	C14—O16—Na1vi	125.73 (13)
O15—Na2—H2W	101.9 (8)	C14—O16—Na2vi	110.77 (13)
O15iv—Na2—H2W	145.3 (8)	Na1vi—O16—Na2vi	80.89 (5)
O1W—Na2—H2W	19.0 (8)	Na1—O1W—Na2	80.11 (5)
O1Wiv—Na2—H2W	112.1 (8)	Na1—O1W—H1W	151 (2)
O16v—Na2—H2W	79.3 (8)	Na2—O1W—H1W	110 (2)
O16ii—Na2—H2W	62.4 (8)	Na1—O1W—H2W	100 (2)
Na1iv—Na2—H2W	125.2 (8)	Na2—O1W—H2W	90 (2)
Na1—Na2—H2W	55.2 (8)	H1W—O1W—H2W	108 (3)
O16i—Na1—Na2—O15	−59.31 (6)	C13—N11—C12—N8	−163.81 (19)
O16ii—Na1—Na2—O15	120.69 (6)	C10—N11—C12—N8	−10.9 (3)
O15iii—Na1—Na2—O15	180.000 (3)	C7—N8—C12—O12	23.0 (3)
O1Wiii—Na1—Na2—O15	46.52 (8)	C9—N8—C12—O12	170.2 (2)
O1W—Na1—Na2—O15	−133.48 (8)	C7—N8—C12—N11	−155.4 (2)
O16i—Na1—Na2—O15iv	−39.26 (7)	C9—N8—C12—N11	−8.1 (3)
O16ii—Na1—Na2—O15iv	140.74 (7)	C12—N11—C13—C14	80.5 (3)
O15iii—Na1—Na2—O15iv	−159.94 (9)	C10—N11—C13—C14	−69.7 (3)
O15—Na1—Na2—O15iv	20.06 (9)	N11—C13—C14—O16	−17.1 (3)
O1Wiii—Na1—Na2—O15iv	66.58 (8)	N11—C13—C14—O15	164.93 (18)
O1W—Na1—Na2—O15iv	−113.42 (8)	O16—C14—O15—Na2	−140.66 (17)
O16i—Na1—Na2—O1W	74.17 (8)	C13—C14—O15—Na2	37.1 (2)
O16ii—Na1—Na2—O1W	−105.83 (8)	O16—C14—O15—Na1	118.07 (19)
O15iii—Na1—Na2—O1W	−46.52 (8)	C13—C14—O15—Na1	−64.2 (2)
O15—Na1—Na2—O1W	133.48 (8)	O15iv—Na2—O15—C14	73.13 (14)
O1Wiii—Na1—Na2—O1W	180.000 (2)	O1W—Na2—O15—C14	−155.86 (15)
O16i—Na1—Na2—O1Wiv	−172.30 (8)	O1Wiv—Na2—O15—C14	−8.69 (18)
O16ii—Na1—Na2—O1Wiv	7.70 (8)	O16v—Na2—O15—C14	128.87 (15)
O15iii—Na1—Na2—O1Wiv	67.01 (9)	O16ii—Na2—O15—C14	−82.65 (15)
O15—Na1—Na2—O1Wiv	−112.99 (9)	Na1iv—Na2—O15—C14	57.82 (16)
O1Wiii—Na1—Na2—O1Wiv	−66.47 (14)	Na1—Na2—O15—C14	−122.29 (16)
O1W—Na1—Na2—O1Wiv	113.53 (14)	O15iv—Na2—O15—Na1	−164.57 (7)
O16i—Na1—Na2—O16v	81.15 (10)	O1W—Na2—O15—Na1	−33.57 (6)
O16ii—Na1—Na2—O16v	−98.85 (10)	O1Wiv—Na2—O15—Na1	113.60 (7)
O15iii—Na1—Na2—O16v	−39.54 (8)	O16v—Na2—O15—Na1	−108.84 (10)
O15—Na1—Na2—O16v	140.46 (8)	O16ii—Na2—O15—Na1	39.65 (4)
O1Wiii—Na1—Na2—O16v	−173.02 (8)	Na1iv—Na2—O15—Na1	−179.885 (9)
O1W—Na1—Na2—O16v	6.98 (8)	O16i—Na1—O15—C14	−99.57 (14)
O16i—Na1—Na2—O16ii	180.000 (1)	O16ii—Na1—O15—C14	80.43 (14)
O15iii—Na1—Na2—O16ii	59.31 (6)	O1Wiii—Na1—O15—C14	−22.69 (15)
O15—Na1—Na2—O16ii	−120.69 (6)	O1W—Na1—O15—C14	157.31 (15)
O1Wiii—Na1—Na2—O16ii	−74.17 (8)	Na2iii—Na1—O15—C14	−56.62 (15)
O1W—Na1—Na2—O16ii	105.83 (8)	Na2—Na1—O15—C14	123.38 (15)
C5—C2—C3—C4	0.2 (4)	O16i—Na1—O15—Na2	137.04 (5)
C5—C2—C3—C7	−176.3 (3)	O16ii—Na1—O15—Na2	−42.96 (5)
C6—N1—C4—C3	−0.6 (5)	O1Wiii—Na1—O15—Na2	−146.07 (6)
C2—C3—C4—N1	0.3 (5)	O1W—Na1—O15—Na2	33.93 (6)
C7—C3—C4—N1	176.9 (3)	Na2iii—Na1—O15—Na2	180.000 (2)
C3—C2—C5—C6	−0.4 (5)	O15—C14—O16—Na1vi	−35.2 (3)
C4—N1—C6—C5	0.4 (5)	C13—C14—O16—Na1vi	147.11 (16)
C4—N1—C6—Cl1	−179.1 (2)	O15—C14—O16—Na2vi	58.5 (2)
C2—C5—C6—N1	0.1 (6)	C13—C14—O16—Na2vi	−119.20 (17)
C2—C5—C6—Cl1	179.6 (3)	O16i—Na1—O1W—Na2	−128.89 (6)
C4—C3—C7—N8	−87.5 (3)	O16ii—Na1—O1W—Na2	51.11 (6)
C2—C3—C7—N8	88.8 (3)	O15iii—Na1—O1W—Na2	147.16 (6)
C3—C7—N8—C12	71.7 (3)	O15—Na1—O1W—Na2	−32.83 (6)
C3—C7—N8—C9	−71.6 (3)	Na2iii—Na1—O1W—Na2	180.000 (1)
C12—N8—C9—C10	22.3 (3)	O15—Na2—O1W—Na1	33.61 (5)
C7—N8—C9—C10	169.0 (2)	O15iv—Na2—O1W—Na1	112.35 (8)
N8—C9—C10—N11	−26.8 (3)	O1Wiv—Na2—O1W—Na1	−113.33 (6)
C9—C10—N11—C12	24.0 (3)	O16v—Na2—O1W—Na1	−174.89 (6)
C9—C10—N11—C13	177.6 (2)	O16ii—Na2—O1W—Na1	−47.43 (5)
C13—N11—C12—O12	17.9 (3)	Na1iv—Na2—O1W—Na1	179.44 (4)
C10—N11—C12—O12	170.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O12v	0.80 (4)	2.02 (4)	2.826 (3)	179 (3)
O1W—H2W···O15ii	0.84 (4)	2.02 (4)	2.822 (2)	158 (3)
C10—H10B···O12vii	0.97	2.54	3.279 (3)	133
C13—H13B···O16ii	0.97	2.49	3.265 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O12i	0.80 (4)	2.02 (4)	2.826 (3)	179 (3)
O1W—H2W⋯O15ii	0.84 (4)	2.02 (4)	2.822 (2)	158 (3)
C10—H10B⋯O12iii	0.97	2.54	3.279 (3)	133
C13—H13B⋯O16ii	0.97	2.49	3.265 (3)	137

Symmetry codes: (i) ; (ii) ; (iii) .