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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o210.
Published online 2007 December 6. doi:  10.1107/S1600536807065038
PMCID: PMC2915271

3,4-Dihydr­oxy-N′-(2-hydroxy­benzyl­idene)benzohydrazide–methanol–water (2/1/3)

Abstract

The asymmetric unit of the title compound, C14H12N2O4·0.5CH4O·1.5H2O, consists of two Schiff base mol­ecules, three water mol­ecules and one methanol mol­ecule. The dihedral angle between the two benzene rings is 7.8 (2)° in one of the mol­ecules and 4.0 (2)° in the other. Intra­molecular O—H(...)O and O—H(...)N hydrogen bonds are observed. Mol­ecules are linked into a three-dimensional network by O—H(...)O and N—H(...)O inter­molecular hydrogen bonds.

Related literature

For the biological properties of Schiff base compounds, see: Brückner et al. (2000 [triangle]); Harrop et al. (2003 [triangle]); Ren et al. (2002 [triangle]). For related structures, see: Diao (2007 [triangle]); Diao et al. (2007 [triangle]); Huang et al. (2007 [triangle]); Li et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o210-scheme1.jpg

Experimental

Crystal data

  • C14H12N2O4·0.5CH4O·1.5H2O
  • M r = 315.30
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o210-efi1.jpg
  • a = 10.707 (2) Å
  • b = 11.994 (2) Å
  • c = 14.103 (3) Å
  • α = 111.56 (3)°
  • β = 103.13 (3)°
  • γ = 104.72 (3)°
  • V = 1522.2 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 (2) K
  • 0.17 × 0.15 × 0.15 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.982, T max = 0.984
  • 9348 measured reflections
  • 6429 independent reflections
  • 2812 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.144
  • S = 0.97
  • 6429 reflections
  • 438 parameters
  • 11 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065038/ci2538sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065038/ci2538Isup2.hkl

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

Acknowledgments

This project is supported by a research grant from Dalian Medical University.

supplementary crystallographic information

Comment

Schiff base compounds have received much attention in recent years. Some of the complexes have been found to have pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). As part of our research programme on the structure of Schiff base compounds (Diao, 2007; Diao et al., 2007; Li et al., 2007; Huang et al., 2007), we report here the structure of the title compound.

The asymmetric unit of the title compound consists of two Schiff base molecules, three water molecules and one methanol molecule (Fig. 1). The corresponding bond lengths and angles in the two Schiff base molecules are nearly identical. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 7.8 (2)° and that between the C15—C20 and C23—C28 benzene rings is 4.0 (2)°. The structure of each molecule is stabilized by O—H···O and O—H···N intramolecular hydrogen bonds.

In the crystal structure, the molecules are linked through intermolecular O—H···O and N—H···O hydrogen bonds (Table 1), forming a three-dimensional network (Fig. 2).

Experimental

Salicylaldehyde (1.0 mmol, 122.1 mg) and 3,4-dihydroxybenzoic acid hydrazide (1.0 mmol, 168.2 mg) were dissolved in a methanol solution (70 ml). The mixture was stirred at room temperature for 1 h and filtered. After keeping the filtrate in air for a week, yellow block-shaped crystals were formed.

Refinement

H atoms of the water molecules and –NH groups were located in a difference Fourier map and refined isotropically, with N—H, O—H and H···H (in water) distances restrained to 0.90 (1) Å, 0.85 (1) Å and 1.37 (2) Å, respectively, and with a fixed Uiso value of 0.08 Å2. The remaining H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H = 0.93–0.96 Å, O—H = 0.82 Å, and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O, Cmethyl).

Figures

Fig. 1.
The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Part of the crystal packing of the title compound.

Crystal data

C14H12N2O4·0.5CH4O·1.5H2OZ = 4
Mr = 315.30F000 = 664
Triclinic, P1Dx = 1.376 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.707 (2) ÅCell parameters from 1027 reflections
b = 11.994 (2) Åθ = 2.6–24.4º
c = 14.103 (3) ŵ = 0.11 mm1
α = 111.56 (3)ºT = 298 (2) K
β = 103.13 (3)ºBlock, yellow
γ = 104.72 (3)º0.17 × 0.15 × 0.15 mm
V = 1522.2 (8) Å3

Data collection

Bruker SMART CCD area-detector diffractometer6429 independent reflections
Radiation source: fine-focus sealed tube2812 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.030
T = 298(2) Kθmax = 26.9º
ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2000)h = −13→9
Tmin = 0.982, Tmax = 0.984k = −14→15
9348 measured reflectionsl = −14→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144  w = 1/[σ2(Fo2) + (0.0505P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
6429 reflectionsΔρmax = 0.17 e Å3
438 parametersΔρmin = −0.21 e Å3
11 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
O10.7795 (2)0.64000 (17)1.35513 (13)0.0587 (6)
H10.76250.56331.33880.088*
O20.7267 (2)0.85547 (16)1.37077 (14)0.0528 (5)
H20.74900.83231.41790.079*
O30.7116 (2)0.39011 (18)0.96456 (14)0.0609 (6)
O40.6696 (2)0.19447 (18)0.67631 (15)0.0605 (6)
H40.67230.25510.72960.091*
O50.6555 (2)0.13711 (18)−0.10815 (14)0.0675 (6)
H50.67010.2132−0.09320.101*
O60.7472 (2)−0.05612 (18)−0.11851 (15)0.0635 (6)
H60.7496−0.0212−0.15860.095*
O70.71818 (18)0.38404 (17)0.28249 (13)0.0490 (5)
O80.7971 (2)0.60616 (18)0.57457 (15)0.0625 (6)
H80.79580.54640.52140.094*
O90.8032 (2)0.04122 (18)0.73419 (16)0.0581 (5)
H90.74700.07010.71280.087*
O100.5614 (2)0.6868 (2)0.83236 (18)0.0619 (6)
O110.8239 (2)0.84887 (19)0.56226 (15)0.0563 (6)
O120.9056 (2)0.11266 (19)0.42584 (19)0.0669 (6)
N10.6301 (2)0.4906 (2)0.87321 (17)0.0401 (5)
N20.6220 (2)0.3958 (2)0.77792 (17)0.0406 (5)
N30.8292 (2)0.30112 (19)0.37667 (17)0.0396 (5)
N40.8380 (2)0.39822 (19)0.47159 (16)0.0382 (5)
C10.6883 (2)0.5837 (2)1.06912 (19)0.0370 (6)
C20.7299 (2)0.5671 (2)1.16190 (19)0.0425 (7)
H2A0.75060.49451.15590.051*
C30.7415 (3)0.6543 (2)1.2623 (2)0.0404 (6)
C40.7141 (3)0.7644 (2)1.2724 (2)0.0401 (6)
C50.6716 (3)0.7821 (2)1.1813 (2)0.0461 (7)
H5A0.65120.85491.18770.055*
C60.6588 (3)0.6929 (2)1.0802 (2)0.0464 (7)
H6A0.63030.70631.01920.056*
C70.6776 (3)0.4813 (3)0.9654 (2)0.0418 (7)
C80.5749 (2)0.4005 (3)0.6887 (2)0.0431 (7)
H8A0.54510.46690.68880.052*
C90.5675 (2)0.3036 (3)0.58771 (19)0.0399 (6)
C100.6148 (3)0.2049 (3)0.5842 (2)0.0457 (7)
C110.6070 (3)0.1131 (3)0.4859 (2)0.0602 (9)
H110.64000.04810.48450.072*
C120.5506 (3)0.1181 (3)0.3907 (3)0.0722 (11)
H120.54360.05540.32450.087*
C130.5047 (3)0.2150 (4)0.3926 (2)0.0697 (10)
H130.46790.21870.32800.084*
C140.5126 (3)0.3074 (3)0.4900 (2)0.0555 (8)
H140.48090.37290.49040.067*
C150.7553 (3)0.1977 (2)0.17858 (19)0.0389 (6)
C160.7038 (3)0.2094 (2)0.0849 (2)0.0447 (7)
H160.67030.27470.08900.054*
C170.7011 (3)0.1264 (3)−0.0143 (2)0.0475 (7)
C180.7470 (3)0.0272 (2)−0.0213 (2)0.0481 (7)
C190.7935 (3)0.0113 (3)0.0699 (2)0.0581 (8)
H190.8221−0.05710.06450.070*
C200.7984 (3)0.0957 (2)0.1699 (2)0.0517 (8)
H200.83060.08430.23140.062*
C210.7657 (3)0.3000 (2)0.2826 (2)0.0385 (6)
C220.8895 (2)0.3959 (2)0.5612 (2)0.0406 (6)
H220.92120.33060.56160.049*
C230.8987 (2)0.4949 (2)0.6626 (2)0.0404 (7)
C240.8529 (3)0.5961 (3)0.6665 (2)0.0462 (7)
C250.8627 (3)0.6882 (3)0.7647 (2)0.0606 (8)
H250.83200.75460.76670.073*
C260.9175 (3)0.6818 (3)0.8592 (3)0.0686 (10)
H260.92410.74450.92520.082*
C270.9630 (3)0.5839 (3)0.8583 (2)0.0653 (9)
H270.99990.58010.92290.078*
C280.9532 (3)0.4917 (3)0.7604 (2)0.0518 (8)
H280.98390.42560.75960.062*
C290.9365 (3)0.1399 (4)0.7883 (3)0.1063 (14)
H29A0.93560.21060.84880.159*
H29B0.96230.16960.73840.159*
H29C1.00190.10660.81450.159*
H30.857 (3)0.238 (2)0.382 (2)0.080*
H11B0.799 (3)0.897 (2)0.6091 (19)0.080*
H12B0.852 (2)0.0381 (15)0.411 (2)0.080*
H1A0.608 (3)0.5579 (19)0.871 (2)0.080*
H12A0.9848 (14)0.110 (3)0.428 (2)0.080*
H11A0.806 (3)0.7774 (15)0.565 (2)0.080*
H10A0.613 (2)0.7585 (17)0.840 (2)0.080*
H10B0.4781 (12)0.677 (3)0.804 (2)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0975 (16)0.0432 (11)0.0340 (11)0.0319 (12)0.0162 (10)0.0165 (9)
O20.0792 (14)0.0403 (11)0.0418 (11)0.0273 (10)0.0260 (11)0.0157 (9)
O30.1012 (16)0.0528 (13)0.0427 (12)0.0477 (12)0.0267 (11)0.0225 (10)
O40.0862 (15)0.0518 (13)0.0495 (13)0.0376 (12)0.0249 (12)0.0205 (11)
O50.1172 (18)0.0582 (13)0.0381 (12)0.0494 (14)0.0273 (11)0.0220 (10)
O60.1113 (17)0.0439 (12)0.0450 (12)0.0406 (12)0.0357 (12)0.0174 (10)
O70.0684 (13)0.0426 (11)0.0432 (11)0.0319 (10)0.0213 (9)0.0185 (9)
O80.0940 (16)0.0526 (13)0.0508 (13)0.0424 (12)0.0278 (12)0.0222 (11)
O90.0649 (14)0.0559 (13)0.0523 (13)0.0294 (11)0.0210 (11)0.0185 (10)
O100.0650 (14)0.0575 (14)0.0714 (15)0.0288 (12)0.0174 (13)0.0375 (13)
O110.0738 (14)0.0496 (13)0.0485 (13)0.0278 (12)0.0303 (10)0.0168 (11)
O120.0593 (14)0.0522 (13)0.0956 (16)0.0269 (12)0.0253 (14)0.0371 (13)
N10.0532 (14)0.0373 (13)0.0330 (13)0.0209 (11)0.0183 (11)0.0146 (11)
N20.0461 (14)0.0429 (13)0.0334 (13)0.0182 (11)0.0158 (10)0.0157 (11)
N30.0494 (14)0.0353 (13)0.0382 (13)0.0191 (11)0.0202 (11)0.0157 (11)
N40.0444 (13)0.0343 (12)0.0326 (13)0.0145 (10)0.0158 (10)0.0107 (10)
C10.0433 (16)0.0346 (15)0.0330 (15)0.0160 (12)0.0144 (12)0.0139 (12)
C20.0541 (17)0.0385 (15)0.0367 (16)0.0246 (14)0.0139 (13)0.0155 (13)
C30.0493 (17)0.0365 (16)0.0343 (15)0.0152 (13)0.0132 (13)0.0164 (13)
C40.0484 (17)0.0315 (15)0.0395 (16)0.0143 (13)0.0195 (13)0.0133 (13)
C50.0668 (19)0.0341 (16)0.0479 (17)0.0263 (14)0.0255 (15)0.0213 (14)
C60.0663 (19)0.0428 (17)0.0372 (16)0.0245 (15)0.0196 (14)0.0218 (14)
C70.0511 (17)0.0421 (17)0.0423 (17)0.0221 (14)0.0210 (13)0.0236 (14)
C80.0419 (16)0.0460 (17)0.0465 (17)0.0165 (13)0.0189 (13)0.0240 (15)
C90.0363 (15)0.0448 (17)0.0320 (15)0.0082 (13)0.0118 (12)0.0154 (13)
C100.0476 (17)0.0429 (17)0.0414 (17)0.0103 (14)0.0208 (14)0.0150 (14)
C110.066 (2)0.0478 (19)0.059 (2)0.0121 (16)0.0345 (17)0.0141 (16)
C120.074 (2)0.060 (2)0.043 (2)−0.0081 (19)0.0279 (18)0.0009 (18)
C130.063 (2)0.083 (3)0.0344 (19)−0.005 (2)0.0102 (15)0.0223 (19)
C140.0486 (18)0.067 (2)0.0442 (18)0.0118 (16)0.0135 (15)0.0269 (17)
C150.0498 (16)0.0331 (15)0.0353 (15)0.0158 (13)0.0191 (13)0.0144 (13)
C160.0624 (19)0.0397 (16)0.0397 (16)0.0274 (14)0.0214 (14)0.0182 (14)
C170.066 (2)0.0400 (17)0.0391 (17)0.0231 (15)0.0198 (15)0.0183 (14)
C180.072 (2)0.0326 (16)0.0368 (16)0.0193 (15)0.0221 (14)0.0108 (13)
C190.094 (2)0.0401 (17)0.0498 (19)0.0364 (17)0.0301 (17)0.0202 (15)
C200.082 (2)0.0402 (17)0.0418 (17)0.0300 (16)0.0247 (15)0.0211 (14)
C210.0483 (17)0.0343 (15)0.0379 (16)0.0162 (13)0.0199 (13)0.0181 (13)
C220.0368 (15)0.0391 (16)0.0443 (17)0.0139 (13)0.0146 (13)0.0172 (14)
C230.0358 (15)0.0408 (16)0.0365 (16)0.0082 (13)0.0110 (12)0.0143 (13)
C240.0454 (17)0.0419 (17)0.0424 (17)0.0091 (14)0.0170 (13)0.0139 (14)
C250.068 (2)0.0479 (19)0.052 (2)0.0184 (16)0.0275 (17)0.0067 (16)
C260.064 (2)0.064 (2)0.043 (2)0.0083 (19)0.0207 (17)−0.0015 (17)
C270.056 (2)0.082 (3)0.0359 (18)0.0100 (19)0.0089 (15)0.0192 (18)
C280.0489 (18)0.0583 (19)0.0454 (18)0.0160 (15)0.0149 (14)0.0245 (16)
C290.066 (3)0.096 (3)0.126 (3)0.015 (2)0.010 (2)0.043 (3)

Geometric parameters (Å, °)

O1—C31.367 (3)C6—H6A0.93
O1—H10.82C8—C91.440 (3)
O2—C41.365 (3)C8—H8A0.93
O2—H20.82C9—C101.390 (4)
O3—C71.234 (3)C9—C141.392 (3)
O4—C101.363 (3)C10—C111.386 (4)
O4—H40.82C11—C121.372 (4)
O5—C171.368 (3)C11—H110.93
O5—H50.82C12—C131.365 (4)
O6—C181.368 (3)C12—H120.93
O6—H60.82C13—C141.380 (4)
O7—C211.240 (3)C13—H130.93
O8—C241.361 (3)C14—H140.93
O8—H80.82C15—C161.384 (3)
O9—C291.416 (3)C15—C201.388 (3)
O9—H90.82C15—C211.484 (3)
O10—H10A0.846 (10)C16—C171.375 (3)
O10—H10B0.85 (2)C16—H160.93
O11—H11B0.85 (3)C17—C181.378 (4)
O11—H11A0.85 (2)C18—C191.370 (4)
O12—H12B0.85 (2)C19—C201.381 (4)
O12—H12A0.85 (2)C19—H190.93
N1—C71.341 (3)C20—H200.93
N1—N21.372 (3)C22—C231.447 (3)
N1—H1A0.91 (3)C22—H220.93
N2—C81.272 (3)C23—C281.388 (3)
N3—C211.340 (3)C23—C241.407 (4)
N3—N41.378 (3)C24—C251.379 (4)
N3—H30.90 (3)C25—C261.367 (4)
N4—C221.273 (3)C25—H250.93
C1—C61.387 (3)C26—C271.379 (4)
C1—C21.387 (3)C26—H260.93
C1—C71.481 (3)C27—C281.376 (4)
C2—C31.372 (3)C27—H270.93
C2—H2A0.93C28—H280.93
C3—C41.388 (3)C29—H29A0.96
C4—C51.373 (3)C29—H29B0.96
C5—C61.383 (3)C29—H29C0.96
C5—H5A0.93
C3—O1—H1109.5C12—C13—C14120.4 (3)
C4—O2—H2109.5C12—C13—H13119.8
C10—O4—H4109.5C14—C13—H13119.8
C17—O5—H5109.5C13—C14—C9120.6 (3)
C18—O6—H6109.5C13—C14—H14119.7
C24—O8—H8109.5C9—C14—H14119.7
C29—O9—H9109.5C16—C15—C20118.5 (2)
H10A—O10—H10B108 (2)C16—C15—C21116.7 (2)
H11B—O11—H11A107 (2)C20—C15—C21124.7 (2)
H12B—O12—H12A108 (2)C17—C16—C15121.4 (3)
C7—N1—N2117.5 (2)C17—C16—H16119.3
C7—N1—H1A123.7 (19)C15—C16—H16119.3
N2—N1—H1A118.7 (19)O5—C17—C16123.3 (3)
C8—N2—N1119.1 (2)O5—C17—C18117.2 (2)
C21—N3—N4117.2 (2)C16—C17—C18119.5 (3)
C21—N3—H3124.4 (19)O6—C18—C19119.2 (3)
N4—N3—H3118.0 (18)O6—C18—C17120.9 (2)
C22—N4—N3118.1 (2)C19—C18—C17119.9 (3)
C6—C1—C2118.0 (2)C18—C19—C20120.8 (3)
C6—C1—C7125.4 (2)C18—C19—H19119.6
C2—C1—C7116.6 (2)C20—C19—H19119.6
C3—C2—C1122.0 (3)C19—C20—C15119.9 (3)
C3—C2—H2A119.0C19—C20—H20120.0
C1—C2—H2A119.0C15—C20—H20120.0
O1—C3—C2123.7 (2)O7—C21—N3120.5 (2)
O1—C3—C4117.0 (2)O7—C21—C15120.6 (2)
C2—C3—C4119.3 (2)N3—C21—C15118.9 (2)
O2—C4—C5118.8 (2)N4—C22—C23119.9 (3)
O2—C4—C3121.6 (2)N4—C22—H22120.1
C5—C4—C3119.6 (2)C23—C22—H22120.1
C4—C5—C6120.7 (3)C28—C23—C24117.7 (3)
C4—C5—H5A119.7C28—C23—C22120.0 (3)
C6—C5—H5A119.7C24—C23—C22122.3 (2)
C5—C6—C1120.4 (2)O8—C24—C25117.9 (3)
C5—C6—H6A119.8O8—C24—C23121.7 (2)
C1—C6—H6A119.8C25—C24—C23120.4 (3)
O3—C7—N1121.3 (2)C26—C25—C24120.0 (3)
O3—C7—C1120.6 (2)C26—C25—H25120.0
N1—C7—C1118.1 (2)C24—C25—H25120.0
N2—C8—C9120.3 (3)C25—C26—C27121.0 (3)
N2—C8—H8A119.8C25—C26—H26119.5
C9—C8—H8A119.8C27—C26—H26119.5
C10—C9—C14118.2 (3)C28—C27—C26119.1 (3)
C10—C9—C8121.8 (2)C28—C27—H27120.4
C14—C9—C8120.0 (3)C26—C27—H27120.4
O4—C10—C11117.7 (3)C27—C28—C23121.7 (3)
O4—C10—C9121.7 (2)C27—C28—H28119.2
C11—C10—C9120.6 (3)C23—C28—H28119.2
C12—C11—C10120.0 (3)O9—C29—H29A109.5
C12—C11—H11120.0O9—C29—H29B109.5
C10—C11—H11120.0H29A—C29—H29B109.5
C13—C12—C11120.2 (3)O9—C29—H29C109.5
C13—C12—H12119.9H29A—C29—H29C109.5
C11—C12—H12119.9H29B—C29—H29C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O10—H10B···O7i0.85 (2)1.96 (1)2.793 (3)168 (3)
O10—H10A···O6ii0.85 (1)2.10 (1)2.938 (3)173 (3)
O11—H11A···O80.85 (2)2.09 (1)2.925 (3)170 (3)
O12—H12A···O11iii0.85 (2)1.94 (1)2.770 (3)165 (3)
N1—H1A···O100.91 (3)1.96 (3)2.844 (3)167 (3)
O12—H12B···O2iv0.85 (2)2.04 (1)2.889 (3)177 (3)
O11—H11B···O9v0.85 (3)1.95 (3)2.765 (3)162 (3)
N3—H3···O120.90 (3)1.96 (3)2.845 (3)165 (3)
O8—H8···N40.821.872.589 (3)146
O6—H6···O9vi0.822.042.834 (3)161
O5—H5···O3vi0.821.862.670 (3)170
O4—H4···N20.821.842.561 (3)146
O2—H2···O10.822.292.725 (3)114
O2—H2···O11vii0.821.932.703 (3)158
O1—H1···O7vii0.821.882.695 (3)172

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2538).

References

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