Tetra­aqua­(pyrimidine-4,6-dicarboxyl­ato-κ2N1,O6)magnesium monohydrate

Starosta, W.; Leciejewicz, J.; Kiegiel, K.

doi:10.1107/S1600536813005850

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page m189

doi:10.1107/S1600536813005850

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Tetraaqua(pyrimidine-4,6-dicarboxylato-κ²N¹,O⁶)magnesium monohydrate

Wojciech Starosta,^a Janusz Leciejewicz ^a ^* and Katarzyna Kiegiel ^a

^aInstitute of Nuclear Chemistry and Technology, ul.Dorodna 16, 03-195 Warszawa, Poland
^*Correspondence e-mail: j.leciejewicz@ichtj.waw.pl

(Received 25 February 2013; accepted 28 February 2013; online 6 March 2013)

In the title compound, [Mg(C₆H₂N₂O₄)(H₂O)₄]·H₂O, the Mg^II ion is coordinated by a fully deprotonated pyrimidine-4,6-dicarboxylate molecule, via a ring N and a carboxylate O atom, and by four water O atoms at the apices of a slightly distorted octahedron. In the crystal, molecules are linked by O—H⋯O and O—H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For the crystal structures of Mg complexes with pyrazine-2,3-dicarboxylic acid, see: Ptasiewicz-Bąk & Leciejewicz (1997 ), with pyrazine-2,5-dicarboxylic acid, see: Ptasiewicz-Bąk & Leciejewicz (1998 ), with pyrazine-2,6-dicarboxylic acid, see: Ptasiewicz-Bąk & Leciejewicz (2003 ) and with pyridazine-3,6-dicarboxylic acid, see: Gryz et al. (2004 ).

Experimental

Crystal data

[Mg(C₆H₂N₂O₄)(H₂O)₄]·H₂O
M_r = 280.49
Monoclinic, P 2₁ /c
a = 7.5633 (15) Å
b = 6.7977 (14) Å
c = 21.605 (4) Å
β = 90.97 (3)°
V = 1110.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.09 mm

Data collection

Kuma KM-4 four-circle diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd., Yarnton, England.]$ ) T_min = 0.947, T_max = 0.975
3485 measured reflections
3246 independent reflections
2187 reflections with I > 2σ(I)
R_int = 0.023
3 standard reflections every 200 reflections intensity decay: 5.10%

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.125
S = 1.01
3246 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H82⋯O2ⁱ	0.87 (3)	1.80 (3)	2.6640 (18)	171 (3)
O5—H51⋯O9ⁱⁱ	0.79 (3)	1.93 (3)	2.7102 (19)	170 (3)
O6—H61⋯N5ⁱⁱⁱ	0.78 (4)	2.29 (4)	2.979 (2)	147 (3)
O6—H62⋯O3^iv	0.90 (3)	1.88 (3)	2.7603 (19)	166 (3)
O8—H81⋯O4ⁱⁱⁱ	0.86 (3)	1.93 (3)	2.779 (2)	174 (2)
O7—H71⋯O4^v	0.90 (3)	1.78 (3)	2.6690 (18)	169 (3)
O5—H52⋯O7^vi	0.77 (3)	2.09 (3)	2.8577 (19)	176 (3)
O9—H91⋯O1^vii	0.77 (3)	2.02 (3)	2.7635 (18)	162 (4)
O9—H92⋯O3^iv	0.81 (3)	1.91 (3)	2.6852 (18)	161 (3)
O7—H72⋯O9	0.85 (3)	1.85 (3)	2.6971 (19)	174 (3)
Symmetry codes: (i) x+1, y, z; (ii) x, y-1, z; (iii) -x+1, -y+1, -z; (iv) -x, -y+1, -z; (v) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vi) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: KM-4 Software (Kuma, 1996 $[Kuma (1996). KM-4 Software. Kuma Diffraction Ltd. Wrocław, Poland.]$ ); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 $[Kuma (2001). DATAPROC. Kuma Diffraction Ltd. Wrocław, Poland.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813005850/su2567sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813005850/su2567Isup2.hkl

checkCIF report

Comment top

Crystal structures of Mg^II complexes with diazine dicarboxylate molecules belong to three types. For example, the structure of a Mg^II complex with pyrazine-2,3-dicarboxylate and water ligands is a catenated polymer (Ptasiewicz-Bąk & Leciejewicz, 1997), while those with pyrazine-2,5-dicarboxylate (Ptasiewicz-Bąk & Leciejewicz, 1998) and pyrazine-2,6-dicarboxylate (Ptasiewicz-Bąk & Leciejewicz, 2003) are composed of hexaquamagnesium(II) cations and fully deprotonated organic molecules.

On the other hand, the Mg^II complex with a pyridazine-3,6-dicarboxylate molecule is built of anions in which the Mg^II ion is coordinated by two water O atoms and two fully deprotonated organic molecules with singly protonated hydrazine molecules as cations (Gryz et al., 2004).

The structure of the title compound, Fig. 1, is built of monomeric molecules in which a Mg^II ion is coordinated by one of the N,O bonding groups of a fully deprotonated pyrimidine-4,6-dicarboxylate molecule and four water O atoms. The coordination geometry of atom Mg1 is a slightly distorted octahedron with typical Mg-N and Mg—O distances [Mg1-N1 = 2.2472 (15) Å; the Mg1-O distances vary from 2.0120 (13) to 2.0896 (15) Å]. The carboxylic groups C7/O1/O2 and C8/O3/O4 are inclined to the pyrimidine ring by 3.5 (1)° and 14.9 (2)°, respectively.

In the crystal, the complexes interact via an extended network of O-H···O and O-H···N hydrogen bonds, in which coordinated and solvate water molecules are donors and the carboxylato O and hetero-ring N atoms act as acceptors, forming a three-dimensional network (Fig. 2 and Table 1).

Related literature top

For the crystal structures of Mg^II complexes with pyrazine-2,3-dicarboxylic acid, see: Ptasiewicz-Bąk & Leciejewicz (1997), with pyrazine-2,5-dicarboxylic acid, see: Ptasiewicz-Bąk & Leciejewicz (1998), with pyrazine-2,6-dicarboxylic acid, see: Ptasiewicz-Bąk & Leciejewicz (2003) and with pyridazine-3,6-dicarboxylic acid, see: Gryz et al. (2004).

Experimental top

An aqueous solution containing 1 mmol of magnesium acetate tetrahydrate and 1 mmol of pyrimidine-4,6-dicarboxylic acid dihydrate were refluxed with constant stirring for 2 h yielding a white precipitate which subsequently was filtered and redissolved in an excess of boiling water. Cooled to room temperature, the solution was left to evaporate. Colourless plate-like crystals deposited after a few days. They were washed with cold ethanol and dried in the air.

Computing details top

Data collection: KM-4 Software (Kuma, 1996); cell refinement: KM-4 Software (Kuma, 1996); data reduction: DATAPROC (Kuma, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

Tetraaqua(pyrimidine-4,6-dicarboxylato-κ²N¹,O⁶)magnesium monohydrate top

Crystal data top

[Mg(C₆H₂N₂O₄)(H₂O)₄]·H₂O	F(000) = 584
M_r = 280.49	D_x = 1.677 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.5633 (15) Å	θ = 6–15°
b = 6.7977 (14) Å	µ = 0.21 mm⁻¹
c = 21.605 (4) Å	T = 293 K
β = 90.97 (3)°	Plates, colourless
V = 1110.6 (4) Å³	0.25 × 0.23 × 0.09 mm
Z = 4

Data collection top

Kuma KM-4 four-circle diffractometer	2187 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 30.1°, θ_min = 1.9°
profile data from ω/2θ scans	h = −10→0
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = 0→9
T_min = 0.947, T_max = 0.975	l = −30→30
3485 measured reflections	3 standard reflections every 200 reflections
3246 independent reflections	intensity decay: 5.1%

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0833P)² + 0.2045P] where P = (F_o² + 2F_c²)/3
3246 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Mg(C₆H₂N₂O₄)(H₂O)₄]·H₂O	V = 1110.6 (4) Å³
M_r = 280.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5633 (15) Å	µ = 0.21 mm⁻¹
b = 6.7977 (14) Å	T = 293 K
c = 21.605 (4) Å	0.25 × 0.23 × 0.09 mm
β = 90.97 (3)°

Data collection top

Kuma KM-4 four-circle diffractometer	2187 reflections with I > 2σ(I)
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	R_int = 0.023
T_min = 0.947, T_max = 0.975	3 standard reflections every 200 reflections
3485 measured reflections	intensity decay: 5.1%
3246 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.47 e Å⁻³
3246 reflections	Δρ_min = −0.26 e Å⁻³
203 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
Mg1	0.32572 (6)	0.46078 (8)	0.15804 (2)	0.01813 (14)
O1	0.05876 (14)	0.42580 (19)	0.14674 (5)	0.0237 (2)
O3	0.00597 (16)	0.06801 (19)	−0.12636 (5)	0.0273 (3)
H82	0.667 (4)	0.431 (4)	0.1337 (12)	0.043 (7)*
O2	−0.16427 (15)	0.3374 (2)	0.08385 (6)	0.0284 (3)
O5	0.36240 (18)	0.1989 (2)	0.20187 (7)	0.0304 (3)
O7	0.30383 (16)	0.59579 (19)	0.24329 (5)	0.0236 (2)
N1	0.29679 (17)	0.3154 (2)	0.06501 (6)	0.0211 (3)
C7	−0.00682 (19)	0.3566 (2)	0.09709 (7)	0.0188 (3)
C2	0.12644 (18)	0.2956 (2)	0.04897 (7)	0.0179 (3)
C3	0.07484 (19)	0.2275 (2)	−0.00879 (7)	0.0200 (3)
H3	−0.0439	0.2128	−0.0196	0.024*
C4	0.2075 (2)	0.1819 (2)	−0.04993 (7)	0.0195 (3)
O6	0.30977 (19)	0.7335 (2)	0.11370 (7)	0.0312 (3)
O4	0.28320 (19)	0.1211 (2)	−0.15411 (6)	0.0355 (3)
C8	0.1616 (2)	0.1171 (2)	−0.11589 (7)	0.0217 (3)
N5	0.37836 (17)	0.1979 (2)	−0.03413 (6)	0.0242 (3)
C6	0.41441 (19)	0.2628 (3)	0.02291 (8)	0.0247 (3)
H6	0.5331	0.2722	0.0344	0.030*
O9	0.12147 (16)	0.9368 (2)	0.24311 (6)	0.0267 (3)
H51	0.290 (4)	0.132 (5)	0.2170 (13)	0.052 (8)*
H61	0.389 (5)	0.794 (5)	0.1006 (15)	0.067 (10)*
H62	0.216 (4)	0.815 (4)	0.1146 (12)	0.046 (7)*
H81	0.629 (3)	0.613 (4)	0.1576 (11)	0.040 (7)*
O8	0.58966 (15)	0.4954 (2)	0.15529 (6)	0.0264 (3)
H71	0.282 (4)	0.526 (4)	0.2778 (13)	0.043 (7)*
H52	0.452 (4)	0.166 (5)	0.2159 (13)	0.050 (8)*
H91	0.069 (4)	0.959 (5)	0.2725 (15)	0.063 (9)*
H92	0.061 (4)	0.939 (5)	0.2119 (14)	0.052 (8)*
H72	0.241 (4)	0.699 (4)	0.2451 (11)	0.038 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mg1	0.0142 (2)	0.0234 (3)	0.0168 (2)	−0.00041 (18)	0.00078 (17)	−0.00113 (18)
O1	0.0172 (5)	0.0342 (6)	0.0199 (5)	−0.0025 (4)	0.0039 (4)	−0.0066 (4)
O3	0.0225 (5)	0.0341 (6)	0.0251 (6)	0.0008 (5)	−0.0041 (4)	−0.0043 (5)
O2	0.0139 (5)	0.0429 (7)	0.0284 (6)	0.0009 (5)	0.0011 (4)	−0.0072 (5)
O5	0.0223 (6)	0.0293 (7)	0.0396 (7)	−0.0006 (5)	−0.0016 (5)	0.0119 (5)
O7	0.0266 (5)	0.0260 (6)	0.0183 (5)	0.0014 (5)	0.0024 (4)	0.0000 (5)
N1	0.0157 (5)	0.0284 (7)	0.0192 (6)	−0.0001 (5)	0.0009 (4)	−0.0028 (5)
C7	0.0147 (6)	0.0219 (7)	0.0198 (6)	0.0009 (5)	0.0025 (5)	−0.0009 (5)
C2	0.0148 (6)	0.0204 (7)	0.0185 (6)	0.0000 (5)	0.0014 (5)	−0.0007 (5)
C3	0.0158 (6)	0.0248 (7)	0.0193 (7)	−0.0018 (5)	0.0010 (5)	−0.0024 (5)
C4	0.0199 (6)	0.0223 (7)	0.0165 (6)	−0.0017 (5)	0.0015 (5)	−0.0018 (5)
O6	0.0238 (6)	0.0307 (6)	0.0394 (7)	0.0042 (5)	0.0085 (5)	0.0103 (5)
O4	0.0368 (7)	0.0463 (8)	0.0238 (6)	−0.0141 (6)	0.0110 (5)	−0.0125 (6)
C8	0.0257 (7)	0.0215 (7)	0.0178 (6)	−0.0013 (6)	0.0006 (5)	−0.0028 (5)
N5	0.0170 (6)	0.0340 (8)	0.0217 (6)	−0.0011 (5)	0.0021 (5)	−0.0051 (5)
C6	0.0134 (6)	0.0383 (9)	0.0225 (7)	0.0000 (6)	0.0009 (5)	−0.0052 (6)
O9	0.0203 (5)	0.0387 (7)	0.0210 (6)	0.0009 (5)	0.0008 (4)	0.0008 (5)
O8	0.0154 (5)	0.0310 (6)	0.0329 (6)	−0.0015 (4)	0.0042 (4)	−0.0036 (5)

Geometric parameters (Å, º) top

Mg1—O8	2.0120 (13)	C7—C2	1.518 (2)
Mg1—O5	2.0331 (15)	C2—C3	1.381 (2)
Mg1—O1	2.0436 (13)	C3—C4	1.387 (2)
Mg1—O7	2.0671 (13)	C3—H3	0.9300
Mg1—O6	2.0896 (15)	C4—N5	1.335 (2)
Mg1—N1	2.2472 (15)	C4—C8	1.526 (2)
O1—C7	1.2650 (19)	O6—H61	0.78 (4)
O3—C8	1.241 (2)	O6—H62	0.90 (3)
O2—C7	1.2270 (19)	O4—C8	1.247 (2)
O5—H51	0.79 (3)	N5—C6	1.333 (2)
O5—H52	0.77 (3)	C6—H6	0.9300
O7—H71	0.90 (3)	O9—H91	0.77 (3)
O7—H72	0.85 (3)	O9—H92	0.81 (3)
N1—C6	1.332 (2)	O8—H82	0.87 (3)
N1—C2	1.3353 (19)	O8—H81	0.86 (3)

O8—Mg1—O5	89.34 (6)	O2—C7—C2	117.67 (13)
O8—Mg1—O1	171.45 (6)	O1—C7—C2	115.28 (13)
O5—Mg1—O1	94.62 (6)	N1—C2—C3	121.66 (13)
O8—Mg1—O7	93.95 (6)	N1—C2—C7	116.35 (13)
O5—Mg1—O7	89.20 (6)	C3—C2—C7	121.98 (13)
O1—Mg1—O7	93.69 (6)	C2—C3—C4	117.23 (13)
O8—Mg1—O6	86.12 (6)	C2—C3—H3	121.4
O5—Mg1—O6	175.43 (6)	C4—C3—H3	121.4
O1—Mg1—O6	89.95 (6)	N5—C4—C3	121.71 (14)
O7—Mg1—O6	90.56 (6)	N5—C4—C8	117.78 (13)
O8—Mg1—N1	96.12 (6)	C3—C4—C8	120.49 (13)
O5—Mg1—N1	92.41 (6)	Mg1—O6—H61	126 (3)
O1—Mg1—N1	76.17 (5)	Mg1—O6—H62	125.1 (17)
O7—Mg1—N1	169.82 (5)	H61—O6—H62	107 (3)
O6—Mg1—N1	88.64 (6)	O3—C8—O4	126.41 (15)
C7—O1—Mg1	121.14 (10)	O3—C8—C4	116.62 (14)
Mg1—O5—H51	128 (2)	O4—C8—C4	116.96 (14)
Mg1—O5—H52	123 (2)	C6—N5—C4	116.43 (13)
H51—O5—H52	106 (3)	N1—C6—N5	126.29 (14)
Mg1—O7—H71	121.5 (17)	N1—C6—H6	116.9
Mg1—O7—H72	117.5 (17)	N5—C6—H6	116.9
H71—O7—H72	107 (2)	H91—O9—H92	113 (3)
C6—N1—C2	116.64 (13)	Mg1—O8—H82	129.2 (18)
C6—N1—Mg1	132.29 (11)	Mg1—O8—H81	117.0 (18)
C2—N1—Mg1	110.81 (10)	H82—O8—H81	105 (3)
O2—C7—O1	127.04 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H82···O2ⁱ	0.87 (3)	1.80 (3)	2.6640 (18)	171 (3)
O5—H51···O9ⁱⁱ	0.79 (3)	1.93 (3)	2.7102 (19)	170 (3)
O6—H61···N5ⁱⁱⁱ	0.78 (4)	2.29 (4)	2.979 (2)	147 (3)
O6—H62···O3^iv	0.90 (3)	1.88 (3)	2.7603 (19)	166 (3)
O8—H81···O4ⁱⁱⁱ	0.86 (3)	1.93 (3)	2.779 (2)	174 (2)
O7—H71···O4^v	0.90 (3)	1.78 (3)	2.6690 (18)	169 (3)
O5—H52···O7^vi	0.77 (3)	2.09 (3)	2.8577 (19)	176 (3)
O9—H91···O1^vii	0.77 (3)	2.02 (3)	2.7635 (18)	162 (4)
O9—H92···O3^iv	0.81 (3)	1.91 (3)	2.6852 (18)	161 (3)
O7—H72···O9	0.85 (3)	1.85 (3)	2.6971 (19)	174 (3)

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

Experimental details

Crystal data
Chemical formula	[Mg(C₆H₂N₂O₄)(H₂O)₄]·H₂O
M_r	280.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.5633 (15), 6.7977 (14), 21.605 (4)
β (°)	90.97 (3)
V (Å³)	1110.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.25 × 0.23 × 0.09

Data collection
Diffractometer	Kuma KM-4 four-circle diffractometer
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.947, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	3485, 3246, 2187
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.125, 1.01
No. of reflections	3246
No. of parameters	203
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.26

Computer programs: KM-4 Software (Kuma, 1996), DATAPROC (Kuma, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H82···O2ⁱ	0.87 (3)	1.80 (3)	2.6640 (18)	171 (3)
O5—H51···O9ⁱⁱ	0.79 (3)	1.93 (3)	2.7102 (19)	170 (3)
O6—H61···N5ⁱⁱⁱ	0.78 (4)	2.29 (4)	2.979 (2)	147 (3)
O6—H62···O3^iv	0.90 (3)	1.88 (3)	2.7603 (19)	166 (3)
O8—H81···O4ⁱⁱⁱ	0.86 (3)	1.93 (3)	2.779 (2)	174 (2)
O7—H71···O4^v	0.90 (3)	1.78 (3)	2.6690 (18)	169 (3)
O5—H52···O7^vi	0.77 (3)	2.09 (3)	2.8577 (19)	176 (3)
O9—H91···O1^vii	0.77 (3)	2.02 (3)	2.7635 (18)	162 (4)
O9—H92···O3^iv	0.81 (3)	1.91 (3)	2.6852 (18)	161 (3)
O7—H72···O9	0.85 (3)	1.85 (3)	2.6971 (19)	174 (3)

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

References

Gryz, M., Starosta, W. & Leciejewicz, J. (2004). J. Coord. Chem. 57, 917–922. Web of Science CSD CrossRef CAS Google Scholar
Kuma (1996). KM-4 Software. Kuma Diffraction Ltd. Wrocław, Poland. Google Scholar
Kuma (2001). DATAPROC. Kuma Diffraction Ltd. Wrocław, Poland. Google Scholar
Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd., Yarnton, England. Google Scholar
Ptasiewicz-Bąk, H. & Leciejewicz, J. (1997). Pol. J. Chem. 71, 493–500. Google Scholar
Ptasiewicz-Bąk, H. & Leciejewicz, J. (1998). J. Coord. Chem. 44, 299–309. CAS Google Scholar
Ptasiewicz-Bąk, H. & Leciejewicz, J. (2003). J. Coord. Chem. 56, 173–180. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 4| April 2013| Page m189

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