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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): m79.
Published online 2009 December 19. doi:  10.1107/S1600536809053768
PMCID: PMC2980135

Aqua­[2-(5-ethyl-2-pyridyl-κN)-4-iso­propyl-4-methyl-5-oxo-4,5-dihydroxy­imidazol-1-ido-κN 1](5-methyl-1H-pyrazole-3-carboxyl­ato-κ2 N 2,O)copper(II) 1.33-hydrate

Abstract

In the title complex, [Cu(C5H5N2O2)(C14H18N3O)(H2O)]·1.33H2O, the CuII ion is coordinated in a slightly distorted square-pyramidal environment. The basal plane is formed by two N atoms from a 2-(5-ethyl-2-pyridyl-κN)-4-isopropyl-4-methyl-5-oxo-4,5-dihydroxy­imidazol-1-ide ligand and by one O atom and one N atom from a 5-methyl-1H-pyrazole-3-carboxyl­ate ligand. The apical position is occupied by a water mol­ecule. In the crystal structure, O—H(...)O, O—H(...)N and N—H(...)O hydrogen bonds lead to a three-dimensional supra­molecular network.

Related literature

For general background to pyrazole and pyridine derivatives, see: Manna et al. (1992 [triangle]); Montoya et al. (2007 [triangle]); Perevalov et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-00m79-scheme1.jpg

Experimental

Crystal data

  • [Cu(C5H5N2O2)(C14H18N3O)(H2O)]·1.33H2O
  • M r = 475.01
  • Trigonal, An external file that holds a picture, illustration, etc.
Object name is e-66-00m79-efi1.jpg
  • a = 26.7859 (3) Å
  • c = 16.6531 (5) Å
  • V = 10347.6 (4) Å3
  • Z = 18
  • Mo Kα radiation
  • μ = 0.99 mm−1
  • T = 296 K
  • 0.50 × 0.40 × 0.35 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.638, T max = 0.723
  • 19606 measured reflections
  • 5619 independent reflections
  • 3406 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.168
  • S = 1.04
  • 5619 reflections
  • 279 parameters
  • H-atom parameters constrained
  • Δρmax = 0.56 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053768/hy2262sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053768/hy2262Isup2.hkl

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

Acknowledgments

This work was supported by the Innovation Project of Guangxi University for Nationalities (gxun-chx2009080).

supplementary crystallographic information

Comment

The chemical and pharmacological properties of heterocyclic derivatives, particularly pyrazole and pyridine derivatives have been investigated extensively because of their chelating ability with metal ions and their potentially beneficial chemical and biological activities (Manna et al., 1992; Montoya et al., 2007; Perevalov et al., 2001). During our research of these types of compounds, a new mixed-ligand copper(II) complex has been synthesized and characterized by single-crystal X-ray diffraction.

As illustrated in Fig. 1, the CuII ion is five-coordinated by three N atoms and two O atoms in a distorted square-pyramidal geometry (Table 1). The basal plane is formed by two N atoms from a 2-(5-ethylpyridin-2-yl)-5-isopropyl-5-methyl-imidazol-4-one ligand and by one O atom and one N atom from a 5-methyl-1H-pyrazole-3-carboxylate ligand. The apical position is occupied by the O atom from a water molecule. The complex molecules and uncoordinated water molecules are held together by hydrogen bonds (Table 2), generating a three-dimensional supramolecular network (Fig. 2).

Experimental

All reagents were available commercially and were used without further purification. A mixture of 5-methyl-1H-pyrazole-3-carboxylatic acid (0.126 g, 1.0 mmol), 2-(5-ethyl-pyridin-2-yl)-5-isopropyl-5-methyl-3,5-dihydro-imidazol-4-one (0.245 g, 1.0 mmol), CuCl2.2H2O (0.170 g, 1.0 mmol), EtOH (10 ml) and H2O (10 ml) was sealed in a 25 ml Teflon-lined bomb and heated to 393 K for 3 d, and then cooled to room temperature. Blue crystals were obtained (yield 32% based on Cu).

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic), 0.98 (CH), 0.97 (CH2) and 0.96 (CH3) Å and N—H= 0.83 Å, and with Uiso(H) = 1.2Ueq(C,N). H atoms of water molecules were located in a difference Fourier map and refined using a riding model, with O—H = 0.85 Å and with Uiso(H) = 1.2Ueq(O).

Figures

Fig. 1.
Molecular structure of the title compound, showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
Fig. 2.
The crystal packing of the title compound, viewed down the c axis.

Crystal data

[Cu(C5H5N2O2)(C14H18N3O)(H2O)]·1.33H2ODx = 1.372 Mg m3
Mr = 475.01Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 6164 reflections
Hall symbol: -R 3θ = 2.6–22.1°
a = 26.7859 (3) ŵ = 0.99 mm1
c = 16.6531 (5) ÅT = 296 K
V = 10347.6 (4) Å3Block, blue
Z = 180.50 × 0.40 × 0.35 mm
F(000) = 4470

Data collection

Bruker APEXII CCD diffractometer5619 independent reflections
Radiation source: fine-focus sealed tube3406 reflections with I > 2σ(I)
graphiteRint = 0.021
[var phi] and ω scansθmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −33→27
Tmin = 0.638, Tmax = 0.723k = −27→34
19606 measured reflectionsl = −21→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0901P)2 + 5.4824P] where P = (Fo2 + 2Fc2)/3
5619 reflections(Δ/σ)max = 0.001
279 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = −0.29 e Å3

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

xyzUiso*/UeqOcc. (<1)
Cu10.150787 (15)0.398671 (15)0.29814 (2)0.05208 (17)
N10.22614 (10)0.46945 (11)0.29242 (18)0.0577 (7)
N20.26293 (11)0.51163 (11)0.34201 (18)0.0604 (7)
H20.25780.51410.39080.072*
N30.14042 (10)0.39308 (10)0.41407 (17)0.0538 (7)
N40.07626 (11)0.33959 (11)0.51314 (18)0.0597 (7)
N50.08268 (10)0.31844 (10)0.30232 (16)0.0489 (6)
O10.33330.66670.5264 (7)0.246 (5)
H10.30910.63520.54860.296*0.67
O20.2584 (3)0.5558 (3)0.6093 (5)0.326 (5)
H2B0.24490.57040.64200.391*
H2A0.23110.53030.58110.391*
O30.22982 (10)0.44486 (11)0.08578 (16)0.0709 (7)
O40.16677 (9)0.39531 (9)0.18320 (14)0.0607 (6)
O50.20666 (10)0.47281 (11)0.48519 (16)0.0834 (8)
O60.09369 (10)0.43745 (10)0.27716 (15)0.0698 (7)
H6B0.06590.41830.24500.084*
H6A0.11700.47170.26200.084*
C10.21357 (13)0.43775 (15)0.1558 (2)0.0572 (8)
C20.24916 (13)0.48057 (13)0.2185 (2)0.0556 (8)
C30.30220 (13)0.53166 (14)0.2216 (3)0.0628 (10)
H30.32730.54960.17890.075*
C40.31003 (13)0.54998 (14)0.2988 (3)0.0629 (9)
C50.35886 (15)0.60083 (15)0.3385 (3)0.0810 (12)
H5A0.34570.60910.38770.121*
H5B0.37320.63360.30340.121*
H5C0.38910.59260.34990.121*
C60.05778 (14)0.28263 (14)0.2408 (2)0.0586 (8)
H60.07490.29440.19050.070*
C70.00924 (15)0.23014 (15)0.2462 (2)0.0664 (9)
C8−0.0143 (2)0.1906 (2)0.1730 (3)0.1164 (19)
H8A−0.00250.21450.12520.140*
H8B0.00370.16700.17100.140*
C9−0.0737 (3)0.1542 (3)0.1694 (4)0.172 (3)
H9A−0.08560.12600.21140.257*
H9B−0.08400.13510.11820.257*
H9C−0.09260.17640.17610.257*
C10−0.01637 (15)0.21426 (13)0.3225 (2)0.0626 (9)
H10−0.05040.17930.32910.075*
C110.00827 (13)0.24971 (13)0.3871 (2)0.0539 (8)
H11−0.00810.23900.43790.065*
C120.05862 (12)0.30228 (12)0.37493 (19)0.0464 (7)
C130.08981 (12)0.34381 (12)0.4392 (2)0.0486 (7)
C140.16219 (14)0.42548 (15)0.4813 (2)0.0642 (9)
C150.12202 (15)0.39227 (15)0.5514 (2)0.0689 (10)
C160.15575 (18)0.37754 (19)0.6134 (3)0.0885 (12)
H16A0.13190.35960.65950.133*
H16B0.18980.41230.62960.133*
H16C0.16650.35160.58960.133*
C170.09624 (19)0.42720 (19)0.5869 (3)0.0949 (14)
H170.12780.46130.61270.114*
C180.0717 (3)0.4477 (2)0.5255 (4)0.132 (2)
H18A0.04690.41630.49100.198*
H18B0.10230.47750.49440.198*
H18C0.04990.46290.55090.198*
C190.0519 (2)0.3941 (2)0.6506 (3)0.132 (2)
H19A0.04050.41900.67600.198*
H19B0.06820.38020.69010.198*
H19C0.01890.36210.62650.198*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0392 (2)0.0468 (2)0.0638 (3)0.01661 (16)0.00573 (17)0.01295 (18)
N10.0401 (13)0.0552 (16)0.0731 (19)0.0204 (12)0.0081 (13)0.0200 (14)
N20.0430 (14)0.0435 (14)0.090 (2)0.0179 (12)−0.0019 (14)0.0079 (14)
N30.0410 (13)0.0460 (14)0.0623 (18)0.0127 (11)0.0032 (12)0.0099 (13)
N40.0491 (15)0.0518 (15)0.0628 (19)0.0137 (12)0.0089 (13)0.0010 (13)
N50.0450 (13)0.0447 (13)0.0545 (16)0.0206 (11)0.0016 (12)0.0094 (12)
O10.255 (8)0.255 (8)0.229 (12)0.127 (4)0.0000.000
O20.278 (9)0.199 (7)0.314 (9)−0.021 (6)0.021 (7)−0.127 (7)
O30.0568 (14)0.0923 (18)0.0720 (17)0.0436 (13)0.0174 (12)0.0276 (14)
O40.0458 (12)0.0623 (14)0.0677 (15)0.0223 (11)0.0077 (11)0.0128 (11)
O50.0602 (15)0.0625 (15)0.0893 (19)0.0020 (12)0.0027 (14)−0.0104 (14)
O60.0606 (13)0.0581 (13)0.0934 (18)0.0317 (11)−0.0160 (13)0.0076 (12)
C10.0462 (17)0.068 (2)0.069 (2)0.0373 (16)0.0083 (17)0.0217 (18)
C20.0415 (15)0.0525 (18)0.078 (2)0.0272 (14)0.0076 (16)0.0224 (17)
C30.0404 (16)0.0566 (19)0.094 (3)0.0260 (15)0.0203 (18)0.0316 (19)
C40.0404 (16)0.0477 (18)0.101 (3)0.0225 (14)0.0122 (18)0.0194 (19)
C50.052 (2)0.051 (2)0.128 (4)0.0171 (16)0.007 (2)0.005 (2)
C60.063 (2)0.0554 (19)0.054 (2)0.0271 (16)0.0028 (16)0.0069 (16)
C70.062 (2)0.055 (2)0.067 (2)0.0179 (17)−0.0054 (18)0.0076 (17)
C80.111 (4)0.083 (3)0.085 (3)−0.005 (3)−0.019 (3)−0.009 (3)
C90.135 (6)0.166 (6)0.135 (6)0.015 (5)−0.027 (4)−0.027 (5)
C100.0569 (19)0.0419 (17)0.075 (2)0.0145 (15)−0.0043 (18)0.0063 (17)
C110.0471 (16)0.0472 (17)0.062 (2)0.0195 (14)−0.0003 (15)0.0085 (15)
C120.0396 (14)0.0406 (15)0.059 (2)0.0200 (12)0.0013 (14)0.0106 (14)
C130.0389 (15)0.0422 (15)0.061 (2)0.0173 (12)0.0030 (14)0.0091 (15)
C140.0512 (19)0.0522 (19)0.074 (2)0.0142 (15)0.0029 (17)−0.0041 (18)
C150.056 (2)0.061 (2)0.069 (2)0.0129 (16)0.0051 (18)−0.0118 (18)
C160.082 (3)0.087 (3)0.069 (3)0.022 (2)−0.010 (2)−0.007 (2)
C170.071 (3)0.077 (3)0.113 (4)0.020 (2)0.015 (3)−0.020 (3)
C180.137 (5)0.106 (4)0.180 (6)0.080 (4)0.022 (4)−0.005 (4)
C190.081 (3)0.125 (4)0.146 (5)0.018 (3)0.036 (3)−0.052 (4)

Geometric parameters (Å, °)

Cu1—N11.962 (2)C6—C71.359 (5)
Cu1—N31.946 (3)C6—H60.9300
Cu1—N52.008 (2)C7—C101.405 (5)
Cu1—O41.973 (2)C7—C81.529 (6)
Cu1—O62.265 (2)C8—C91.391 (7)
N1—C21.341 (4)C8—H8A0.9700
N1—N21.348 (4)C8—H8B0.9700
N2—C41.367 (4)C9—H9A0.9600
N2—H20.8300C9—H9B0.9600
N3—C141.357 (4)C9—H9C0.9600
N3—C131.402 (3)C10—C111.367 (5)
N4—C131.272 (4)C10—H100.9300
N4—C151.473 (4)C11—C121.394 (4)
N5—C61.332 (4)C11—H110.9300
N5—C121.336 (4)C12—C131.467 (4)
O1—H10.8500C14—C151.535 (5)
O2—H2B0.8501C15—C171.532 (6)
O2—H2A0.8501C15—C161.547 (6)
O3—C11.226 (4)C16—H16A0.9600
O4—C11.283 (4)C16—H16B0.9600
O5—C141.233 (4)C16—H16C0.9600
O6—H6B0.8498C17—C181.462 (7)
O6—H6A0.8499C17—C191.506 (6)
C1—C21.490 (5)C17—H170.9800
C2—C31.396 (4)C18—H18A0.9600
C3—C41.355 (5)C18—H18B0.9600
C3—H30.9300C18—H18C0.9600
C4—C51.490 (5)C19—H19A0.9600
C5—H5A0.9600C19—H19B0.9600
C5—H5B0.9600C19—H19C0.9600
C5—H5C0.9600
N3—Cu1—N199.25 (11)C9—C8—H8B108.1
N3—Cu1—O4170.05 (10)C7—C8—H8B108.1
N1—Cu1—O481.68 (11)H8A—C8—H8B107.3
N3—Cu1—N582.23 (10)C8—C9—H9A109.5
N1—Cu1—N5168.82 (10)C8—C9—H9B109.5
O4—Cu1—N594.97 (10)H9A—C9—H9B109.5
N3—Cu1—O694.89 (10)C8—C9—H9C109.5
N1—Cu1—O698.84 (10)H9A—C9—H9C109.5
O4—Cu1—O694.75 (9)H9B—C9—H9C109.5
N5—Cu1—O692.05 (9)C11—C10—C7120.6 (3)
C2—N1—N2108.3 (3)C11—C10—H10119.7
C2—N1—Cu1113.3 (2)C7—C10—H10119.7
N2—N1—Cu1138.4 (2)C10—C11—C12118.3 (3)
N1—N2—C4108.7 (3)C10—C11—H11120.9
N1—N2—H2125.8C12—C11—H11120.9
C14—N3—C13105.1 (3)N5—C12—C11121.7 (3)
C14—N3—Cu1140.4 (2)N5—C12—C13114.5 (2)
C13—N3—Cu1113.7 (2)C11—C12—C13123.8 (3)
C13—N4—C15105.7 (3)N4—C13—N3118.1 (3)
C6—N5—C12118.4 (3)N4—C13—C12127.6 (3)
C6—N5—Cu1127.1 (2)N3—C13—C12114.3 (3)
C12—N5—Cu1114.3 (2)O5—C14—N3125.9 (3)
H2B—O2—H2A109.3O5—C14—C15126.4 (3)
C1—O4—Cu1116.2 (2)N3—C14—C15107.7 (3)
Cu1—O6—H6B114.0N4—C15—C17109.8 (3)
Cu1—O6—H6A104.0N4—C15—C14103.4 (3)
H6B—O6—H6A114.4C17—C15—C14109.8 (3)
O3—C1—O4126.1 (3)N4—C15—C16110.9 (3)
O3—C1—C2120.4 (3)C17—C15—C16113.4 (4)
O4—C1—C2113.5 (3)C14—C15—C16109.0 (3)
N1—C2—C3108.3 (3)C15—C16—H16A109.5
N1—C2—C1115.2 (3)C15—C16—H16B109.5
C3—C2—C1136.5 (3)H16A—C16—H16B109.5
C4—C3—C2106.6 (3)C15—C16—H16C109.5
C4—C3—H3126.7H16A—C16—H16C109.5
C4—N2—H2125.5H16B—C16—H16C109.5
C2—C3—H3126.7C18—C17—C19110.1 (5)
C3—C4—N2108.1 (3)C18—C17—C15112.6 (4)
C3—C4—C5131.2 (3)C19—C17—C15112.1 (4)
N2—C4—C5120.8 (4)C18—C17—H17107.2
C4—C5—H5A109.5C19—C17—H17107.2
C4—C5—H5B109.5C15—C17—H17107.2
H5A—C5—H5B109.5C17—C18—H18A109.5
C4—C5—H5C109.5C17—C18—H18B109.5
H5A—C5—H5C109.5H18A—C18—H18B109.5
H5B—C5—H5C109.5C17—C18—H18C109.5
N5—C6—C7124.7 (3)H18A—C18—H18C109.5
N5—C6—H6117.6H18B—C18—H18C109.5
C7—C6—H6117.6C17—C19—H19A109.5
C6—C7—C10116.3 (3)C17—C19—H19B109.5
C6—C7—C8121.0 (3)H19A—C19—H19B109.5
C10—C7—C8122.8 (3)C17—C19—H19C109.5
C9—C8—C7116.8 (5)H19A—C19—H19C109.5
C9—C8—H8A108.1H19B—C19—H19C109.5
C7—C8—H8A108.1
N3—Cu1—N1—C2171.2 (2)Cu1—N5—C6—C7−175.2 (3)
O4—Cu1—N1—C21.2 (2)N5—C6—C7—C101.6 (5)
N5—Cu1—N1—C274.4 (6)N5—C6—C7—C8−176.6 (4)
O6—Cu1—N1—C2−92.3 (2)C6—C7—C8—C9−149.2 (6)
N3—Cu1—N1—N2−8.8 (3)C10—C7—C8—C932.7 (8)
O4—Cu1—N1—N2−178.8 (3)C6—C7—C10—C11−2.1 (5)
N5—Cu1—N1—N2−105.6 (6)C8—C7—C10—C11176.1 (4)
O6—Cu1—N1—N287.7 (3)C7—C10—C11—C121.2 (5)
C2—N1—N2—C4−0.1 (3)C6—N5—C12—C11−0.8 (4)
Cu1—N1—N2—C4179.9 (2)Cu1—N5—C12—C11174.9 (2)
N1—Cu1—N3—C1415.1 (4)C6—N5—C12—C13178.6 (3)
N5—Cu1—N3—C14−176.1 (4)Cu1—N5—C12—C13−5.8 (3)
O6—Cu1—N3—C14−84.7 (4)C10—C11—C12—N50.3 (4)
N1—Cu1—N3—C13−177.3 (2)C10—C11—C12—C13−179.1 (3)
N5—Cu1—N3—C13−8.5 (2)C15—N4—C13—N30.0 (4)
O6—Cu1—N3—C1382.9 (2)C15—N4—C13—C12179.4 (3)
N3—Cu1—N5—C6−176.8 (3)C14—N3—C13—N4−0.8 (4)
N1—Cu1—N5—C6−78.3 (6)Cu1—N3—C13—N4−172.6 (2)
O4—Cu1—N5—C6−6.4 (3)C14—N3—C13—C12179.7 (3)
O6—Cu1—N5—C688.6 (3)Cu1—N3—C13—C127.9 (3)
N3—Cu1—N5—C128.0 (2)N5—C12—C13—N4179.3 (3)
N1—Cu1—N5—C12106.4 (6)C11—C12—C13—N4−1.4 (5)
O4—Cu1—N5—C12178.4 (2)N5—C12—C13—N3−1.3 (4)
O6—Cu1—N5—C12−86.6 (2)C11—C12—C13—N3178.1 (3)
N1—Cu1—O4—C1−2.7 (2)C13—N3—C14—O5−179.6 (4)
N5—Cu1—O4—C1−171.9 (2)Cu1—N3—C14—O5−11.4 (6)
O6—Cu1—O4—C195.6 (2)C13—N3—C14—C151.1 (4)
Cu1—O4—C1—O3−176.6 (2)Cu1—N3—C14—C15169.3 (3)
Cu1—O4—C1—C23.4 (3)C13—N4—C15—C17117.8 (4)
N2—N1—C2—C3−0.2 (3)C13—N4—C15—C140.7 (4)
Cu1—N1—C2—C3179.76 (19)C13—N4—C15—C16−116.0 (3)
N2—N1—C2—C1−179.9 (2)O5—C14—C15—N4179.6 (4)
Cu1—N1—C2—C10.1 (3)N3—C14—C15—N4−1.2 (4)
O3—C1—C2—N1177.7 (3)O5—C14—C15—C1762.4 (5)
O4—C1—C2—N1−2.3 (4)N3—C14—C15—C17−118.3 (4)
O3—C1—C2—C3−1.8 (5)O5—C14—C15—C16−62.4 (5)
O4—C1—C2—C3178.2 (3)N3—C14—C15—C16116.9 (3)
N1—C2—C3—C40.5 (3)N4—C15—C17—C18−63.5 (5)
C1—C2—C3—C4−180.0 (3)C14—C15—C17—C1849.6 (5)
C2—C3—C4—N2−0.6 (3)C16—C15—C17—C18171.8 (4)
C2—C3—C4—C5178.4 (3)N4—C15—C17—C1961.3 (5)
N1—N2—C4—C30.5 (3)C14—C15—C17—C19174.4 (4)
N1—N2—C4—C5−178.6 (3)C16—C15—C17—C19−63.4 (5)
C12—N5—C6—C7−0.2 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O20.852.122.965 (10)172
O2—H2A···O50.852.082.838 (7)148
O2—H2B···O2i0.852.413.246 (10)168
O6—H6A···O3ii0.852.142.807 (3)135
O6—H6B···N4iii0.852.072.861 (3)154
N2—H2···O50.832.012.733 (3)144

Symmetry codes: (i) y−1/3, −x+y+1/3, −z+4/3; (ii) y−1/3, −x+y+1/3, −z+1/3; (iii) −y+1/3, xy+2/3, z−1/3.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2262).

References

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