Hexaaqua­cadmium(II) dipicrate monohydrate

Natarajan, S.; Moovendaran, K.; Dhas, S.A.M.B.; Suresh, J.; Lakshman, P.L.N.

doi:10.1107/S1600536809015049

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page m620

doi:10.1107/S1600536809015049

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Hexaaquacadmium(II) dipicrate monohydrate

S. Natarajan,^a K. Moovendaran,^a S. A. Martin Britto Dhas,^a J. Suresh ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, Madurai Kamaraj University, Madurai 625 021, India, ^bDepartment of Physics, The Madura College, Madurai 625 011, India, and ^cDepartment of Food Science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: nilanthalakshman@yahoo.co.uk

(Received 3 April 2009; accepted 22 April 2009; online 7 May 2009)

In the structure of the title compound, [Cd(H₂O)₆](C₆H₂N₃O₇)₂·H₂O, the Cd^II ion is located on an inversion center and is coordinated by six water molecules in an octahedral geometry. The picrate anions have no coordination interactions with the Cd^II ion. The three nitro groups are twisted away from the attached benzene ring, making dihedral angles of 17.89 (3), 27.94 (4) and 13.65 (3)°. There are numerous O—H⋯O hydrogen bonds in the crystal structure, involving coordinated and uncoordinated water molecules.

Related literature

Picric acid forms salts with many organic and metallic cations, see: Gartland et al. (1974 ). Crystal structures have been reported for NH₄ and K picrates (Maartmann-Moe, 1969 ), thallium picrate (Herbstein et al., 1977 ), manganese picrate (Liu et al., 2008 ) and zinc picrate (Natarajan et al., 2008 ). For bond angles in picric acid, see: Yang et al. (2001 ).

Experimental

Crystal data

[Cd(H₂O)₆](C₆H₂N₃O₇)₂·H₂O
M_r = 712.75
Orthorhombic, P b n b
a = 7.2823 (2) Å
b = 13.2249 (4) Å
c = 25.3798 (8) Å
V = 2444.27 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 293 K
0.18 × 0.15 × 0.11 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.834, T_max = 0.895
2247 measured reflections
2142 independent reflections
1513 reflections with I > 2σ(I)
R_int = 0.010
2 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.084
S = 1.16
2142 reflections
220 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H1W⋯O1ⁱ	0.73 (5)	2.25 (6)	2.923 (4)	155 (6)
O8—H3W⋯O3ⁱⁱ	0.79 (5)	2.09 (5)	2.882 (4)	172 (5)
O8—H4W⋯O10ⁱⁱⁱ	0.80 (2)	1.96 (2)	2.758 (5)	171 (5)
O9—H5W⋯O6^iv	0.85 (5)	2.59 (5)	2.951 (4)	107 (4)
O9—H5W⋯O7^iv	0.85 (5)	2.10 (5)	2.905 (5)	159 (5)
O10—H9W⋯O11^iv	0.75 (6)	2.30 (5)	2.993 (5)	154 (5)
O11—H2W⋯O6	0.88 (6)	2.54 (5)	2.953 (4)	109 (4)
O11—H2W⋯O7	0.88 (6)	2.01 (6)	2.877 (4)	166 (5)
O9—H6W⋯O10	0.81 (4)	1.97 (2)	2.763 (5)	167 (5)
O10—H8W⋯O1	0.87 (7)	2.18 (7)	2.891 (4)	140 (5)
O10—H8W⋯O7	0.87 (7)	2.20 (7)	2.936 (4)	142 (6)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iv) -x+1, -y+1, -z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015049/bq2135sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015049/bq2135Isup2.hkl

checkCIF report

Comment top

Picric acid forms salts with many organic and metallic cations (Gartland et al., 1974). Crystal structures have been reported for isomorphous NH₄ and K picrates (Maartmann-Moe, 1969), thallium picrate (Herbstein et al., 1977), recently for manganese picrate (Liu et al., 2008) and zinc picrate (Natarajan et al., 2008). This work is part of a systematic investigation on the structures of the metal complexes of picric acid.

In the structure of the title compound, each Cd^II ion is coordinated by the O atoms of six water molecules (Fig. 1). The Cd—O distances range from 2.219 (3)Å to 2.299 (3)Å. The coordination polyhedra around the Cd^II ion can be described as a distorted octahedron. The picrate anion adopts a keto form with a C6—O7 bond distance of 1.250 (4)Å; the C1—C6 [1.444 (5)Å] and C5—C6 [1.454 (5)Å] bond distances are longer than the other C—C bond lengths of the benzene ring. The three nitro groups are twisted out of the attached benzene ring by 17.89 (3)° [N1/O1/O2], 27.94 (4)° [N2/O5/O6] and 13.65 (3)° [N3/O3/O4]. The twisting of these nitro groups may be attributed to the O—H···O hydrogen bonding interactions taking place between water and picrate O atoms. The C5—C6—C1 bond angle (111.8 (3)°) is smaller than the corresponding angle in picric acid (116.4 (5)°; Yang et al., 2001). The packing of the molecules is governed by the large number of O—H···O hydrogen bonds (Table 1).

Related literature top

Picric acid forms salts with many organic and metallic cations, see: Gartland et al. (1974). Crystal structures have been reported for isomorphous NH₄ and K picrates (Maartmann-Moe, 1969), thallium picrate (Herbstein et al., 1977), manganese picrate (Liu et al., 2008) and zinc picrate (Natarajan et al., 2008). For bond angles in picric acid, see: Yang et al. (2001).

Experimental top

Colorless needle-shaped single crystals of the title compound were grown from a saturated aqueous solution containing picric acid and cadmium chloride in a 1:1 stoichiometric ratio.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Hexaaquacadmium(II) dipicrate monohydrate top

Crystal data top

[Cd(H₂O)₆](C₆H₂N₃O₇)₂·H₂O	F(000) = 1432
M_r = 712.75	D_x = 1.937 Mg m⁻³
Orthorhombic, Pbnb	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2bc 2ab	Cell parameters from 25 reflections
a = 7.2823 (2) Å	θ = 3–25°
b = 13.2249 (4) Å	µ = 1.01 mm⁻¹
c = 25.3798 (8) Å	T = 293 K
V = 2444.27 (13) Å³	Block, colourless
Z = 4	0.18 × 0.15 × 0.11 mm

Data collection top

Nonius MACH-3 diffractometer	1513 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.010
Graphite monochromator	θ_max = 25.0°, θ_min = 2.9°
ω–2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
T_min = 0.834, T_max = 0.895	l = −1→30
2247 measured reflections	2 standard reflections every 60 min
2142 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0314P)² + 3.7212P] where P = (F_o² + 2F_c²)/3
S = 1.16	(Δ/σ)_max < 0.001
2142 reflections	Δρ_max = 0.54 e Å⁻³
220 parameters	Δρ_min = −0.38 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0029 (2)

Crystal data top

[Cd(H₂O)₆](C₆H₂N₃O₇)₂·H₂O	V = 2444.27 (13) Å³
M_r = 712.75	Z = 4
Orthorhombic, Pbnb	Mo Kα radiation
a = 7.2823 (2) Å	µ = 1.01 mm⁻¹
b = 13.2249 (4) Å	T = 293 K
c = 25.3798 (8) Å	0.18 × 0.15 × 0.11 mm

Data collection top

Nonius MACH-3 diffractometer	1513 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.010
T_min = 0.834, T_max = 0.895	2 standard reflections every 60 min
2247 measured reflections	intensity decay: none
2142 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	2 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	Δρ_max = 0.54 e Å⁻³
2142 reflections	Δρ_min = −0.38 e Å⁻³
220 parameters

Special details top

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
Cd	0.0000	0.5000	0.0000	0.03236 (15)
O11	0.1978 (4)	0.5718 (3)	0.05990 (11)	0.0393 (7)
O1	0.4465 (5)	0.2509 (2)	0.11321 (10)	0.0581 (9)
O5	0.6784 (4)	0.6893 (2)	0.18800 (10)	0.0430 (7)
O7	0.4862 (4)	0.4516 (2)	0.10554 (9)	0.0390 (7)
O2	0.3391 (4)	0.1969 (2)	0.18648 (10)	0.0435 (7)
O6	0.5121 (4)	0.6525 (2)	0.12019 (9)	0.0415 (7)
O4	0.5772 (5)	0.5100 (2)	0.34801 (10)	0.0463 (7)
N3	0.5092 (4)	0.4393 (2)	0.32448 (11)	0.0297 (7)
O8	−0.0269 (6)	0.3512 (2)	0.04266 (13)	0.0609 (10)
O9	0.2500 (5)	0.4420 (3)	−0.03995 (13)	0.0554 (9)
O3	0.4428 (4)	0.3650 (2)	0.34660 (10)	0.0430 (7)
O10	0.5209 (5)	0.3302 (2)	0.00923 (13)	0.0457 (8)
N2	0.5770 (4)	0.6320 (2)	0.16356 (11)	0.0301 (7)
C4	0.5398 (5)	0.5320 (3)	0.24176 (14)	0.0280 (8)
H4	0.5694	0.5898	0.2608	0.034*
N1	0.4123 (5)	0.2622 (2)	0.15992 (11)	0.0336 (7)
C2	0.4606 (5)	0.3554 (3)	0.23989 (13)	0.0290 (8)
H2	0.4336	0.2958	0.2577	0.035*
C3	0.5024 (5)	0.4423 (3)	0.26750 (12)	0.0279 (8)
C6	0.4911 (5)	0.4481 (3)	0.15474 (13)	0.0272 (7)
C1	0.4592 (5)	0.3581 (3)	0.18566 (13)	0.0286 (8)
C5	0.5328 (5)	0.5350 (3)	0.18776 (13)	0.0258 (8)
H8W	0.517 (8)	0.337 (5)	0.043 (3)	0.09 (2)*
H1W	0.172 (8)	0.607 (4)	0.081 (2)	0.07 (2)*
H3W	−0.009 (7)	0.350 (4)	0.074 (2)	0.065 (16)*
H5W	0.302 (7)	0.475 (4)	−0.0643 (19)	0.063 (16)*
H2W	0.276 (8)	0.536 (4)	0.0788 (19)	0.067 (17)*
H6W	0.317 (5)	0.402 (3)	−0.0255 (15)	0.045 (13)*
H9W	0.612 (8)	0.349 (4)	−0.0004 (19)	0.06 (2)*
H4W	−0.007 (7)	0.297 (2)	0.0302 (19)	0.065 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd	0.0329 (2)	0.0278 (2)	0.0363 (2)	0.00038 (17)	−0.00396 (18)	−0.00312 (16)
O11	0.0433 (17)	0.0432 (17)	0.0314 (14)	0.0014 (14)	−0.0075 (13)	−0.0079 (14)
O1	0.109 (3)	0.0353 (16)	0.0295 (15)	−0.0106 (17)	0.0057 (16)	−0.0099 (12)
O5	0.0509 (18)	0.0310 (15)	0.0470 (15)	−0.0088 (13)	−0.0122 (14)	0.0002 (13)
O7	0.0649 (19)	0.0298 (13)	0.0221 (12)	0.0003 (13)	−0.0042 (13)	−0.0018 (11)
O2	0.0614 (19)	0.0269 (15)	0.0423 (15)	−0.0055 (14)	−0.0051 (14)	0.0004 (12)
O6	0.066 (2)	0.0324 (14)	0.0260 (13)	−0.0018 (14)	−0.0045 (13)	0.0039 (11)
O4	0.0609 (18)	0.0510 (18)	0.0270 (13)	−0.0151 (16)	−0.0020 (13)	−0.0087 (13)
N3	0.0297 (16)	0.0375 (18)	0.0220 (14)	−0.0003 (15)	−0.0011 (14)	−0.0031 (13)
O8	0.118 (3)	0.0330 (16)	0.0312 (16)	0.004 (2)	−0.0078 (19)	0.0040 (13)
O9	0.058 (2)	0.063 (2)	0.0451 (17)	0.0244 (19)	0.0174 (17)	0.0129 (17)
O3	0.0582 (18)	0.0428 (16)	0.0281 (13)	−0.0079 (15)	−0.0016 (13)	0.0068 (12)
O10	0.051 (2)	0.0435 (17)	0.0426 (19)	−0.0074 (16)	0.0016 (16)	−0.0024 (14)
N2	0.0346 (16)	0.0271 (16)	0.0286 (15)	0.0041 (14)	0.0019 (14)	−0.0006 (13)
C4	0.026 (2)	0.0300 (17)	0.0278 (18)	0.0014 (15)	−0.0025 (14)	−0.0070 (15)
N1	0.0434 (19)	0.0268 (16)	0.0306 (16)	0.0010 (15)	−0.0037 (15)	−0.0016 (14)
C2	0.033 (2)	0.0288 (17)	0.0255 (18)	0.0020 (16)	−0.0023 (14)	0.0026 (14)
C3	0.0279 (17)	0.0334 (19)	0.0225 (16)	0.0027 (16)	−0.0020 (16)	−0.0017 (14)
C6	0.0287 (18)	0.0272 (17)	0.0256 (17)	0.0017 (15)	−0.0010 (16)	−0.0022 (14)
C1	0.035 (2)	0.0238 (17)	0.0268 (17)	0.0012 (16)	−0.0043 (15)	−0.0030 (14)
C5	0.028 (2)	0.0239 (16)	0.0256 (16)	0.0022 (14)	−0.0013 (14)	0.0004 (14)

Geometric parameters (Å, º) top

Cd—O9ⁱ	2.221 (3)	O8—H3W	0.79 (5)
Cd—O9	2.221 (3)	O8—H4W	0.80 (2)
Cd—O8ⁱ	2.255 (3)	O9—H5W	0.85 (5)
Cd—O8	2.255 (3)	O9—H6W	0.81 (4)
Cd—O11	2.299 (3)	O10—H8W	0.87 (7)
Cd—O11ⁱ	2.299 (3)	O10—H9W	0.75 (6)
O11—H1W	0.73 (5)	N2—C5	1.459 (5)
O11—H2W	0.88 (6)	C4—C5	1.372 (5)
O1—N1	1.220 (4)	C4—C3	1.382 (5)
O5—N2	1.226 (4)	C4—H4	0.9300
O7—C6	1.250 (4)	N1—C1	1.467 (4)
O2—N1	1.219 (4)	C2—C1	1.377 (5)
O6—N2	1.228 (4)	C2—C3	1.380 (5)
O4—N3	1.216 (4)	C2—H2	0.9300
N3—O3	1.231 (4)	C6—C1	1.444 (5)
N3—C3	1.447 (4)	C6—C5	1.454 (5)

O9ⁱ—Cd—O9	180.00 (15)	H5W—O9—H6W	113 (5)
O9ⁱ—Cd—O8ⁱ	89.37 (14)	H8W—O10—H9W	108 (5)
O9—Cd—O8ⁱ	90.63 (14)	O5—N2—O6	123.3 (3)
O9ⁱ—Cd—O8	90.63 (14)	O5—N2—C5	117.6 (3)
O9—Cd—O8	89.37 (14)	O6—N2—C5	119.1 (3)
O8ⁱ—Cd—O8	180.00 (16)	C5—C4—C3	119.3 (3)
O9ⁱ—Cd—O11	93.97 (13)	C5—C4—H4	120.4
O9—Cd—O11	86.03 (13)	C3—C4—H4	120.4
O8ⁱ—Cd—O11	84.41 (13)	O2—N1—O1	122.7 (3)
O8—Cd—O11	95.59 (13)	O2—N1—C1	117.9 (3)
O9ⁱ—Cd—O11ⁱ	86.03 (13)	O1—N1—C1	119.4 (3)
O9—Cd—O11ⁱ	93.97 (13)	C1—C2—C3	119.2 (3)
O8ⁱ—Cd—O11ⁱ	95.59 (13)	C1—C2—H2	120.4
O8—Cd—O11ⁱ	84.41 (13)	C3—C2—H2	120.4
O11—Cd—O11ⁱ	180.00 (11)	C2—C3—C4	121.2 (3)
Cd—O11—H1W	126 (5)	C2—C3—N3	119.5 (3)
Cd—O11—H2W	123 (3)	C4—C3—N3	119.3 (3)
H1W—O11—H2W	96 (5)	O7—C6—C1	124.7 (3)
O4—N3—O3	123.4 (3)	O7—C6—C5	123.5 (3)
O4—N3—C3	118.9 (3)	C1—C6—C5	111.8 (3)
O3—N3—C3	117.7 (3)	C2—C1—C6	124.3 (3)
Cd—O8—H3W	118 (4)	C2—C1—N1	115.1 (3)
Cd—O8—H4W	126 (4)	C6—C1—N1	120.5 (3)
H3W—O8—H4W	110 (5)	C4—C5—C6	124.1 (3)
Cd—O9—H5W	122 (3)	C4—C5—N2	115.9 (3)
Cd—O9—H6W	121 (3)	C6—C5—N2	119.9 (3)

C1—C2—C3—C4	1.1 (6)	O2—N1—C1—C2	16.5 (5)
C1—C2—C3—N3	−178.2 (3)	O1—N1—C1—C2	−163.9 (4)
C5—C4—C3—C2	0.8 (6)	O2—N1—C1—C6	−160.4 (3)
C5—C4—C3—N3	−179.8 (3)	O1—N1—C1—C6	19.2 (5)
O4—N3—C3—C2	167.0 (3)	C3—C4—C5—C6	−1.1 (5)
O3—N3—C3—C2	−14.0 (5)	C3—C4—C5—N2	−179.0 (3)
O4—N3—C3—C4	−12.3 (5)	O7—C6—C5—C4	−179.6 (4)
O3—N3—C3—C4	166.7 (3)	C1—C6—C5—C4	−0.4 (5)
C3—C2—C1—C6	−2.9 (6)	O7—C6—C5—N2	−1.8 (5)
C3—C2—C1—N1	−179.7 (3)	C1—C6—C5—N2	177.4 (3)
O7—C6—C1—C2	−178.4 (4)	O5—N2—C5—C4	26.6 (5)
C5—C6—C1—C2	2.5 (5)	O6—N2—C5—C4	−153.5 (3)
O7—C6—C1—N1	−1.8 (6)	O5—N2—C5—C6	−151.4 (3)
C5—C6—C1—N1	179.1 (3)	O6—N2—C5—C6	28.5 (5)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11—H1W···O1ⁱⁱ	0.73 (5)	2.25 (6)	2.923 (4)	155 (6)
O8—H3W···O3ⁱⁱⁱ	0.79 (5)	2.09 (5)	2.882 (4)	172 (5)
O8—H4W···O10^iv	0.80 (2)	1.96 (2)	2.758 (5)	171 (5)
O9—H5W···O6^v	0.85 (5)	2.59 (5)	2.951 (4)	107 (4)
O9—H5W···O7^v	0.85 (5)	2.10 (5)	2.905 (5)	159 (5)
O10—H9W···O11^v	0.75 (6)	2.30 (5)	2.993 (5)	154 (5)
C4—H4···O2^vi	0.93	2.57	3.195 (4)	125
O11—H2W···O6	0.88 (6)	2.54 (5)	2.953 (4)	109 (4)
O11—H2W···O7	0.88 (6)	2.01 (6)	2.877 (4)	166 (5)
O9—H6W···O10	0.81 (4)	1.97 (2)	2.763 (5)	167 (5)
O10—H8W···O1	0.87 (7)	2.18 (7)	2.891 (4)	140 (5)
O10—H8W···O7	0.87 (7)	2.20 (7)	2.936 (4)	142 (6)

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

Experimental details

Crystal data
Chemical formula	[Cd(H₂O)₆](C₆H₂N₃O₇)₂·H₂O
M_r	712.75
Crystal system, space group	Orthorhombic, Pbnb
Temperature (K)	293
a, b, c (Å)	7.2823 (2), 13.2249 (4), 25.3798 (8)
V (Å³)	2444.27 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.18 × 0.15 × 0.11

Data collection
Diffractometer	Nonius MACH-3 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.834, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	2247, 2142, 1513
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.084, 1.16
No. of reflections	2142
No. of parameters	220
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.38

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11—H1W···O1ⁱ	0.73 (5)	2.25 (6)	2.923 (4)	155 (6)
O8—H3W···O3ⁱⁱ	0.79 (5)	2.09 (5)	2.882 (4)	172 (5)
O8—H4W···O10ⁱⁱⁱ	0.80 (2)	1.96 (2)	2.758 (5)	171 (5)
O9—H5W···O6^iv	0.85 (5)	2.59 (5)	2.951 (4)	107 (4)
O9—H5W···O7^iv	0.85 (5)	2.10 (5)	2.905 (5)	159 (5)
O10—H9W···O11^iv	0.75 (6)	2.30 (5)	2.993 (5)	154 (5)
C4—H4···O2^v	0.93	2.57	3.195 (4)	124.9
O11—H2W···O6	0.88 (6)	2.54 (5)	2.953 (4)	109 (4)
O11—H2W···O7	0.88 (6)	2.01 (6)	2.877 (4)	166 (5)
O9—H6W···O10	0.81 (4)	1.97 (2)	2.763 (5)	167 (5)
O10—H8W···O1	0.87 (7)	2.18 (7)	2.891 (4)	140 (5)
O10—H8W···O7	0.87 (7)	2.20 (7)	2.936 (4)	142 (6)

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

Acknowledgements

The authors thank the DST for the FIST program.

References

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