Poly[μ2-aqua-μ4-(2-{3-[(6-chloro­pyridin-3-yl)meth­yl]-2-oxoimidazolidin-1-yl}acetato)-sodium]

Kant, R.; Gupta, V.K.; Kapoor, K.; Shripanavar, C.S.; Banerjee, K.; Deshmukh, M.B.

doi:10.1107/S1600536812025007

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages m891-m892

https://doi.org/10.1107/S1600536812025007

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Poly[μ₂-aqua-μ₄-(2-{3-[(6-chloropyridin-3-yl)methyl]-2-oxoimidazolidin-1-yl}acetato)-sodium]

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a Chetan S. Shripanavar,^b Kaushik Banerjee ^c and Madhukar B. Deshmukh ^b

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, ^bDepartment of Chemistry, Shivaji University, Kolhapur, 416 004, India, and ^cNational Research Centre for Grapes, Pune 412 307, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 22 May 2012; accepted 1 June 2012; online 13 June 2012)

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 octahedral 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 molecules, forming a two-dimensional structure parallel to (100). There are intermolecular 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_r = 309.68
Monoclinic, C 2/c
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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.112
S = 1.02
2678 reflections
191 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.46 e Å⁻³

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) $[-x+2, y+1, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812025007/lh5481sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025007/lh5481Isup2.hkl

checkCIF report

Comment top

For the development of nicotinoid insecticides the crucial turning-point could be traced back to the work done by the scientists from Nihon Tokushu Noyaku Seizo K and Nippon Bayer (Legocki & Polec, 2008). Insects become resistant to insecticides due to continuous use and hence it is imperative to introduce new molecules having novel mode of action (Kovganko & Kashkan, 2004). The outstanding development of neonicotinoid insecticides has been achieved for the modern crop protection, consumer products, and animal health markets between 1990 and today reflects the enormous importance of this chemical class (Zhao et al., 2009). Neonicotinoids have low toxicity toward mammals and no teratogenic or mutagenic effects (Xu et al., 2010). The biological activity and agricultural uses of neonicotinoid insecticides are enormous (Zhao et al., 2009). From investigations it is revealed that the neonicotinoids are converted into numerous and variable metabolites in plants as well as in mammals (Tanner et al., 2010).

The asymmetric unit is shown in Fig. 1. The bond lengths and angles observed in (I) show normal values and are comparable to those in related structures (Kapoor et al., 2011; Kant et al., 2012). There are two independent Na^I ions, one of which lies on an inversion center and is coordinated in a slightly disotorted octahedral 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 imidazole ring adopts half-chair conformation (asymmetry parameter: ΔC₂(C9—C10) = 2.31). The Na^I ions bridge organic ligands and solvent water molecules to form a two-dimensional structure parallel to (100). There are intermolecular O—H···O and weak C—H···O hydrogen bonds within the two-dimensional structure.

Related literature top

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 et al. (1975). For related structures, see: Kapoor et al. (2011, 2012); Kant et al. (2012).

Experimental top

Ethyl[3-[(6-chloropyridin-3-yl)methyl]-2-(nitroimino)imidazolidin -1-yl]acetate (0.341 g m, 0.001 mol) was dissolved in 5 ml methanol and 5 ml 1 N NaOH solution was added. The reaction mixture was refluxed on a water bath at 343K for 12 h, and then cooled. The compound was re-precipitated upon neutralization with 1 N HCl. The compound was dissolved in methanol and crystallized in a fume hood at room temperature by the process of slow evaporation.

m.p. 575 K IR (KBr) ν_max: 3421, 3300, 2872, 2930, 1668, 1606 cm^-1. LC—MS/MS: 270, 252, 224, 149, 126 m/z.

Structure description top

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 et al. (1975). For related structures, see: Kapoor et al. (2011, 2012); Kant et al. (2012).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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).

Figures top

	Fig. 1. The asymmetric unit with ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure. The broken lines show the intermolecular C—H···O and O—H···O interactions. Only H atoms involved in hydrogen bonds have been shown.

Poly[µ₂-aqua-µ₄-(2-{3-[(6-chloropyridin-3-yl)methyl]-2-oxoimidazolidin- 1-yl}acetato)-sodium] top

Crystal data top

[Na(C₁₁H₁₁ClN₃O₃)(H₂O)]	F(000) = 1280
M_r = 309.68	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2678 independent reflections
Radiation source: fine-focus sealed tube	1909 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.6°
ω scan	h = −56→52
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→5
T_min = 0.836, T_max = 1.000	l = −15→15
9498 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: 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(F_o²) + (0.0459P)² + 2.523P] where P = (F_o² + 2F_c²)/3
2678 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Na(C₁₁H₁₁ClN₃O₃)(H₂O)]	V = 2744.2 (2) Å³
M_r = 309.68	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 45.655 (2) Å	µ = 0.33 mm⁻¹
b = 4.9113 (2) Å	T = 293 K
c = 12.5205 (7) Å	0.3 × 0.2 × 0.1 mm
β = 102.184 (5)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2678 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	1909 reflections with I > 2σ(I)
T_min = 0.836, T_max = 1.000	R_int = 0.038
9498 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.44 e Å⁻³
2678 reflections	Δρ_min = −0.46 e Å⁻³
191 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—O15^iv	2.3611 (16)	C9—H9B	0.9700
Na2—O1W	2.4432 (18)	C10—N11	1.448 (3)
Na2—O1W^iv	2.4432 (18)	C10—H10A	0.9700
Na2—O16^v	2.4969 (16)	C10—H10B	0.9700
Na2—O16ⁱⁱ	2.4968 (16)	N11—C12	1.353 (3)
Na2—Na1^iv	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—Na1^vi	2.3239 (14)
C3—C4	1.374 (4)	O16—Na2^vi	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—O15^iv	82.15 (8)	N8—C9—H9B	111.4
O15—Na2—O1W	88.91 (5)	C10—C9—H9B	111.4
O15^iv—Na2—O1W	130.33 (6)	H9A—C9—H9B	109.2
O15—Na2—O1W^iv	130.33 (6)	N11—C10—C9	101.8 (2)
O15^iv—Na2—O1W^iv	88.91 (6)	N11—C10—H10A	111.4
O1W—Na2—O1W^iv	130.75 (10)	C9—C10—H10A	111.4
O15—Na2—O16^v	150.63 (6)	N11—C10—H10B	111.4
O15^iv—Na2—O16^v	81.11 (5)	C9—C10—H10B	111.4
O1W—Na2—O16^v	83.79 (6)	H10A—C10—H10B	109.3
O1W^iv—Na2—O16^v	73.25 (6)	C12—N11—C13	122.9 (2)
O15—Na2—O16ⁱⁱ	81.11 (5)	C12—N11—C10	110.4 (2)
O15^iv—Na2—O16ⁱⁱ	150.63 (6)	C13—N11—C10	120.80 (19)
O1W—Na2—O16ⁱⁱ	73.25 (6)	O12—C12—N11	127.1 (2)
O1W^iv—Na2—O16ⁱⁱ	83.79 (6)	O12—C12—N8	124.4 (2)
O16^v—Na2—O16ⁱⁱ	123.21 (8)	N11—C12—N8	108.5 (2)
O15—Na2—Na1^iv	129.79 (5)	N11—C13—C14	114.54 (18)
O15^iv—Na2—Na1^iv	49.71 (3)	N11—C13—H13A	108.6
O1W—Na2—Na1^iv	130.64 (5)	C14—C13—H13A	108.6
O1W^iv—Na2—Na1^iv	49.63 (4)	N11—C13—H13B	108.6
O16^v—Na2—Na1^iv	47.14 (3)	C14—C13—H13B	108.6
O16ⁱⁱ—Na2—Na1^iv	133.19 (4)	H13A—C13—H13B	107.6
O15—Na2—Na1	49.71 (3)	O16—C14—O15	125.69 (19)
O15^iv—Na2—Na1	129.79 (5)	O16—C14—C13	117.84 (18)
O1W—Na2—Na1	49.63 (4)	O15—C14—C13	116.43 (18)
O1W^iv—Na2—Na1	130.65 (5)	C14—O15—Na2	122.53 (12)
O16^v—Na2—Na1	133.19 (4)	C14—O15—Na1	121.41 (12)
O16ⁱⁱ—Na2—Na1	47.14 (3)	Na2—O15—Na1	81.97 (5)
Na1^iv—Na2—Na1	179.49 (4)	C14—O16—Na1^vi	125.73 (13)
O15—Na2—H2W	101.9 (8)	C14—O16—Na2^vi	110.77 (13)
O15^iv—Na2—H2W	145.3 (8)	Na1^vi—O16—Na2^vi	80.89 (5)
O1W—Na2—H2W	19.0 (8)	Na1—O1W—Na2	80.11 (5)
O1W^iv—Na2—H2W	112.1 (8)	Na1—O1W—H1W	151 (2)
O16^v—Na2—H2W	79.3 (8)	Na2—O1W—H1W	110 (2)
O16ⁱⁱ—Na2—H2W	62.4 (8)	Na1—O1W—H2W	100 (2)
Na1^iv—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—O15^iv	−39.26 (7)	C9—N8—C12—N11	−8.1 (3)
O16ⁱⁱ—Na1—Na2—O15^iv	140.74 (7)	C12—N11—C13—C14	80.5 (3)
O15ⁱⁱⁱ—Na1—Na2—O15^iv	−159.94 (9)	C10—N11—C13—C14	−69.7 (3)
O15—Na1—Na2—O15^iv	20.06 (9)	N11—C13—C14—O16	−17.1 (3)
O1Wⁱⁱⁱ—Na1—Na2—O15^iv	66.58 (8)	N11—C13—C14—O15	164.93 (18)
O1W—Na1—Na2—O15^iv	−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)	O15^iv—Na2—O15—C14	73.13 (14)
O1Wⁱⁱⁱ—Na1—Na2—O1W	180.000 (2)	O1W—Na2—O15—C14	−155.86 (15)
O16ⁱ—Na1—Na2—O1W^iv	−172.30 (8)	O1W^iv—Na2—O15—C14	−8.69 (18)
O16ⁱⁱ—Na1—Na2—O1W^iv	7.70 (8)	O16^v—Na2—O15—C14	128.87 (15)
O15ⁱⁱⁱ—Na1—Na2—O1W^iv	67.01 (9)	O16ⁱⁱ—Na2—O15—C14	−82.65 (15)
O15—Na1—Na2—O1W^iv	−112.99 (9)	Na1^iv—Na2—O15—C14	57.82 (16)
O1Wⁱⁱⁱ—Na1—Na2—O1W^iv	−66.47 (14)	Na1—Na2—O15—C14	−122.29 (16)
O1W—Na1—Na2—O1W^iv	113.53 (14)	O15^iv—Na2—O15—Na1	−164.57 (7)
O16ⁱ—Na1—Na2—O16^v	81.15 (10)	O1W—Na2—O15—Na1	−33.57 (6)
O16ⁱⁱ—Na1—Na2—O16^v	−98.85 (10)	O1W^iv—Na2—O15—Na1	113.60 (7)
O15ⁱⁱⁱ—Na1—Na2—O16^v	−39.54 (8)	O16^v—Na2—O15—Na1	−108.84 (10)
O15—Na1—Na2—O16^v	140.46 (8)	O16ⁱⁱ—Na2—O15—Na1	39.65 (4)
O1Wⁱⁱⁱ—Na1—Na2—O16^v	−173.02 (8)	Na1^iv—Na2—O15—Na1	−179.885 (9)
O1W—Na1—Na2—O16^v	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—Na1^vi	−35.2 (3)
C4—N1—C6—C5	0.4 (5)	C13—C14—O16—Na1^vi	147.11 (16)
C4—N1—C6—Cl1	−179.1 (2)	O15—C14—O16—Na2^vi	58.5 (2)
C2—C5—C6—N1	0.1 (6)	C13—C14—O16—Na2^vi	−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)	O15^iv—Na2—O1W—Na1	112.35 (8)
N8—C9—C10—N11	−26.8 (3)	O1W^iv—Na2—O1W—Na1	−113.33 (6)
C9—C10—N11—C12	24.0 (3)	O16^v—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)	Na1^iv—Na2—O1W—Na1	179.44 (4)
C10—N11—C12—O12	170.9 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O12^v	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···O12^vii	0.97	2.54	3.279 (3)	133
C13—H13B···O16ⁱⁱ	0.97	2.49	3.265 (3)	137

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

Experimental details

Crystal data
Chemical formula	[Na(C₁₁H₁₁ClN₃O₃)(H₂O)]
M_r	309.68
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	45.655 (2), 4.9113 (2), 12.5205 (7)
β (°)	102.184 (5)
V (Å³)	2744.2 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.836, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9498, 2678, 1909
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.112, 1.02
No. of reflections	2678
No. of parameters	191
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.46

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+2, y+1, −z+1/2; (ii) x, y+1, z; (iii) x, −y+1, z−1/2.

Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. He is also thankful to the University of Jammu, Jammu, India, for financial support.

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