supplementary materials


cv5383 scheme

Acta Cryst. (2013). E69, m127    [ doi:10.1107/S1600536813002122 ]

Diaqua(5-carboxybenzene-1,3-dicarboxylato-[kappa]O1)[8-ethyl-5-oxo-2-(piperazin-4-ium-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylato-[kappa]2O5,O6]zinc monohydrate

Z.-L. Ye, G.-H. Xin, F.-T. Zhang and D.-R. Xiao

Abstract top

In the title compound, [Zn(C14H17N5O3)(C9H4O6)(H2O)2]·H2O, the complex molecule exists in a zwitterionic form. The ZnII ion exhibits a distorted tetragonal-pyramidal geometry, being coordinated by two O atoms from the zwitterionic 8-ethyl-5-oxo-2-(piperazin-4-ium-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate (L) ligand, one O atom from the 5-carboxybenzene-1,3-dicarboxylate dianion, [Hbtc]2-, and two O atoms from two aqua ligands. In the crystal, N-H...O and O-H...O hydrogen bonds link the components into a three-dimensional structure. The crystal packing exhibits [pi]-[pi] interactions between the aromatic rings, with centroid-centroid distances in the range 3.466 (3)-3.667 (3) Å.

Comment top

Pipemidic acid (8-ethyl-5-oxo-2-piperazin-1-yl-5,8-dihydropyrido[2,3-d]pyrimidine-6- carboxylic acid), L, is a member of quinolones used to treat various infections (Mizuki et al., 1996). The complexes of the L ligand and [Hbtc]2- anion have not been reported till now. In this paper, we report the crystal structure of the title compound.

The asymmetric unit of the title compound is composed of one ZnII ion, one L ligand , one [Hbtc]2- anion (H3btc = benzene-1,3,5-tricarboxylic acid), two coordinated and one lattice water molecules (Fig. 1). All bond lengths in L are normal, though slightly different from those reported for base molecule L earlier by Zhang et al. (2011). So, the C1—O2, C3—O3 and C1—O1 bond lengths are 1.255 (2), 1.275 (2) and 1.255 (2) Å, respectively, versus 1.219 (2), 1.268 (3) and 1.319 (3) Å reported by Zhang et al. (2011).

In the crystal, intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) link all moieties into three-dimensional supramolecular structure. The crystal packing exhibits ππ interactions between the aromatic rings with the intercentroids distances covering the range 3.466 (3) – 3.667 (3) Å.

Related literature top

For general background to the use of quinolones in the treatment of infections, see: Mizuki et al. (1996). For the crystal structure of a related compound, see: Zhang et al. (2011).

Experimental top

A mixture of Zn(OAC)2.3H2O (0.546 g, 0.25 mmol), L (0.758 g, 0.25 mmol), H3btc(0.526 g, 0.25 mmol) and distilled water (8 mL) was stirred for 20 min in air. The mixture was then transferred to a 23 ml Teflon-lined hydrothermal bomb. The bomb was kept at 423 K for 96 h under autogenous pressure. Upon cooling, colorless block of 1 was obtained from the reaction mixture.

Refinement top

C-bound H atoms were positioned geometrically [C—H = 0.97 Å] and refined using a riding model approximation, with Uiso(H) = 1.2 – 1.5 Ueq(C). The N- and O-bound H atoms were located on a difference Fourier map, but placed in idealized positions [N—H = 0.90 Å, O—H = 0.82-0.85 Å] and refined as riding, with Uiso(H) =1.2 Ueq of the parent atom.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the title compound showing the atomic numbering and 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
Diaqua(5-carboxybenzene-1,3-dicarboxylato-κO1)[8-ethyl-5-oxo-2-(piperazin-4-ium-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylato-κ2O5,O6]zinc monohydrate top
Crystal data top
[Zn(C14H17N5O3)(C9H4O6)(H2O)2]·H2OF(000) = 1304
Mr = 630.87Dx = 1.711 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12140 reflections
a = 13.5019 (11) Åθ = 1.9–25.0°
b = 12.5743 (10) ŵ = 1.08 mm1
c = 17.7314 (10) ÅT = 293 K
β = 125.575 (4)°Block, colourless
V = 2448.5 (3) Å30.42 × 0.38 × 0.35 mm
Z = 4
Data collection top
Bruker APEX CCD area-detector
diffractometer
4299 independent reflections
Radiation source: fine-focus sealed tube3894 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
phi and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1613
Tmin = 0.659, Tmax = 0.703k = 1410
12140 measured reflectionsl = 1921
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 0.86 w = 1/[σ2(Fo2) + (0.105P)2]
where P = (Fo2 + 2Fc2)/3
4299 reflections(Δ/σ)max = 0.001
370 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
[Zn(C14H17N5O3)(C9H4O6)(H2O)2]·H2OV = 2448.5 (3) Å3
Mr = 630.87Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.5019 (11) ŵ = 1.08 mm1
b = 12.5743 (10) ÅT = 293 K
c = 17.7314 (10) Å0.42 × 0.38 × 0.35 mm
β = 125.575 (4)°
Data collection top
Bruker APEX CCD area-detector
diffractometer
4299 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
3894 reflections with I > 2σ(I)
Tmin = 0.659, Tmax = 0.703Rint = 0.019
12140 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.105Δρmax = 0.30 e Å3
S = 0.86Δρmin = 0.29 e Å3
4299 reflectionsAbsolute structure: ?
370 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
Zn10.032037 (19)0.542603 (16)0.212780 (15)0.02453 (12)
O10.00857 (14)0.45417 (12)0.31957 (11)0.0390 (4)
OW10.14163 (14)0.42573 (12)0.12210 (10)0.0334 (3)
HW1A0.10430.36930.13750.040*
HW1B0.18240.43830.06590.040*
N10.82562 (16)0.33637 (14)0.38179 (12)0.0336 (4)
H1A0.89060.33030.37990.040*
H1B0.77580.28120.35010.040*
C10.07412 (17)0.39071 (15)0.37520 (13)0.0248 (4)
OW20.03717 (14)0.61280 (11)0.10620 (10)0.0345 (3)
HW2A0.01690.59590.10020.041*
HW2B0.05300.67740.09630.041*
O20.06097 (13)0.32612 (11)0.42274 (10)0.0340 (3)
N20.68419 (14)0.42975 (13)0.42967 (11)0.0244 (4)
C20.19476 (16)0.39307 (14)0.38844 (12)0.0219 (4)
C2O0.37837 (16)0.76072 (14)0.26753 (12)0.0220 (4)
OW30.77949 (16)0.23797 (14)0.71317 (12)0.0509 (4)
HW3A0.82730.28430.71770.061*
HW3B0.78540.18270.68960.061*
O30.15171 (13)0.53636 (10)0.28385 (10)0.0284 (3)
N30.50374 (15)0.52444 (12)0.35526 (11)0.0248 (4)
C30.28179 (17)0.32237 (15)0.45016 (13)0.0249 (4)
H3A0.26100.27590.47970.030*
O40.13831 (13)0.64086 (11)0.21967 (10)0.0324 (3)
N40.54190 (14)0.37213 (12)0.45188 (10)0.0220 (3)
C40.42950 (16)0.38277 (14)0.42995 (12)0.0197 (4)
O50.01241 (12)0.74802 (11)0.31946 (10)0.0309 (3)
N50.39455 (14)0.31466 (12)0.47158 (10)0.0239 (3)
C50.57379 (17)0.44147 (14)0.41227 (12)0.0210 (4)
O60.12766 (16)1.06302 (13)0.42602 (13)0.0456 (4)
C60.39329 (18)0.53030 (14)0.33426 (13)0.0226 (4)
H6A0.34260.58420.29430.027*
O70.28043 (13)1.03074 (11)0.43593 (10)0.0290 (3)
C70.34660 (17)0.46027 (13)0.36832 (12)0.0196 (4)
O80.58074 (13)0.74380 (12)0.22537 (10)0.0338 (3)
C80.22443 (18)0.46717 (14)0.34316 (13)0.0212 (4)
O90.51412 (13)0.62674 (12)0.16984 (10)0.0361 (4)
H9A0.58830.60670.14020.054*
C90.76274 (19)0.34109 (17)0.48758 (14)0.0303 (4)
H9B0.71560.27590.46810.036*
H9C0.79430.35430.55180.036*
C100.86758 (18)0.32865 (19)0.47921 (14)0.0346 (5)
H10A0.92770.38350.51540.042*
H10B0.90620.26020.50420.042*
C110.7598 (2)0.43770 (19)0.33365 (17)0.0377 (5)
H11A0.68510.42100.27390.045*
H11B0.81020.48070.32310.045*
C120.73005 (19)0.49977 (17)0.39075 (16)0.0329 (5)
H12A0.80260.53590.44060.040*
H12B0.66920.55320.35220.040*
C130.48182 (19)0.23716 (16)0.54400 (14)0.0321 (5)
H13A0.56420.25820.56760.039*
H13B0.47430.23930.59510.039*
C140.4609 (3)0.1272 (2)0.5085 (2)0.0662 (9)
H14A0.51910.08060.55750.099*
H14B0.47000.12420.45880.099*
H14C0.38010.10530.48620.099*
C150.09348 (16)0.71577 (14)0.27897 (12)0.0215 (4)
C160.17983 (16)0.76464 (14)0.29685 (12)0.0212 (4)
C170.15124 (17)0.85606 (15)0.35071 (12)0.0212 (4)
H17A0.07470.88700.37960.025*
C180.23701 (16)0.90140 (14)0.36141 (12)0.0212 (4)
C190.34947 (17)0.85178 (15)0.32052 (12)0.0234 (4)
H19A0.40600.88020.32890.028*
C210.29326 (16)0.71805 (15)0.25523 (13)0.0233 (4)
H21A0.31290.65770.21870.028*
C220.50197 (17)0.70998 (15)0.21896 (12)0.0244 (4)
C230.21103 (17)1.00653 (16)0.41192 (13)0.0249 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01950 (17)0.02615 (18)0.03055 (17)0.00258 (8)0.01604 (13)0.00079 (8)
O10.0278 (8)0.0537 (10)0.0451 (9)0.0111 (6)0.0268 (8)0.0178 (7)
OW10.0390 (9)0.0277 (7)0.0291 (7)0.0004 (6)0.0173 (7)0.0011 (6)
N10.0305 (10)0.0413 (10)0.0381 (10)0.0043 (8)0.0251 (8)0.0010 (8)
C10.0241 (10)0.0273 (10)0.0284 (10)0.0039 (8)0.0183 (9)0.0062 (8)
OW20.0375 (8)0.0330 (8)0.0440 (8)0.0068 (6)0.0300 (7)0.0054 (6)
O20.0332 (8)0.0350 (8)0.0461 (9)0.0001 (6)0.0299 (7)0.0057 (7)
N20.0200 (8)0.0278 (8)0.0292 (8)0.0033 (7)0.0165 (7)0.0035 (7)
C20.0218 (9)0.0231 (9)0.0246 (9)0.0021 (7)0.0156 (8)0.0042 (7)
C2O0.0194 (9)0.0243 (9)0.0236 (9)0.0008 (7)0.0133 (8)0.0039 (7)
OW30.0491 (11)0.0523 (11)0.0622 (11)0.0057 (8)0.0385 (9)0.0089 (8)
O30.0205 (7)0.0287 (8)0.0363 (8)0.0047 (5)0.0166 (7)0.0079 (6)
N30.0217 (9)0.0237 (8)0.0308 (9)0.0016 (6)0.0162 (7)0.0034 (7)
C30.0257 (10)0.0262 (10)0.0272 (10)0.0032 (8)0.0179 (8)0.0015 (8)
O40.0277 (8)0.0298 (7)0.0427 (8)0.0010 (6)0.0221 (7)0.0108 (6)
N40.0194 (8)0.0240 (8)0.0234 (8)0.0011 (6)0.0128 (7)0.0003 (6)
C40.0202 (9)0.0204 (9)0.0184 (8)0.0010 (7)0.0111 (7)0.0027 (7)
O50.0215 (7)0.0334 (8)0.0406 (8)0.0005 (6)0.0196 (7)0.0063 (6)
N50.0217 (8)0.0249 (8)0.0258 (8)0.0011 (6)0.0143 (7)0.0030 (6)
C50.0198 (10)0.0222 (9)0.0217 (9)0.0009 (7)0.0124 (8)0.0043 (7)
O60.0497 (11)0.0391 (9)0.0693 (12)0.0188 (8)0.0467 (10)0.0230 (8)
C60.0214 (10)0.0214 (9)0.0252 (9)0.0008 (7)0.0137 (8)0.0007 (7)
O70.0244 (8)0.0345 (8)0.0291 (7)0.0061 (6)0.0161 (7)0.0030 (6)
C70.0183 (10)0.0201 (9)0.0200 (9)0.0011 (6)0.0109 (8)0.0034 (6)
O80.0228 (7)0.0394 (8)0.0424 (8)0.0011 (6)0.0208 (7)0.0019 (7)
C80.0201 (10)0.0210 (9)0.0232 (9)0.0016 (7)0.0130 (8)0.0049 (7)
O90.0242 (8)0.0423 (9)0.0443 (9)0.0121 (6)0.0213 (7)0.0137 (7)
C90.0251 (10)0.0382 (12)0.0309 (10)0.0078 (8)0.0182 (9)0.0057 (9)
C100.0248 (11)0.0461 (13)0.0335 (11)0.0086 (9)0.0173 (9)0.0055 (9)
C110.0343 (12)0.0461 (13)0.0431 (13)0.0048 (10)0.0284 (11)0.0065 (10)
C120.0284 (11)0.0321 (11)0.0469 (12)0.0013 (9)0.0268 (10)0.0054 (10)
C130.0305 (11)0.0338 (11)0.0332 (11)0.0074 (9)0.0192 (9)0.0138 (9)
C140.096 (2)0.0375 (14)0.0573 (17)0.0229 (15)0.0402 (17)0.0114 (13)
C150.0228 (10)0.0189 (9)0.0234 (9)0.0048 (7)0.0139 (8)0.0058 (7)
C160.0182 (9)0.0237 (9)0.0228 (9)0.0042 (7)0.0125 (8)0.0045 (7)
C170.0175 (9)0.0233 (9)0.0211 (9)0.0025 (7)0.0104 (7)0.0034 (7)
C180.0219 (9)0.0234 (9)0.0201 (9)0.0030 (7)0.0132 (8)0.0035 (7)
C190.0218 (9)0.0283 (10)0.0242 (9)0.0049 (8)0.0157 (8)0.0039 (7)
C210.0230 (9)0.0216 (9)0.0263 (9)0.0005 (7)0.0150 (8)0.0010 (7)
C220.0209 (9)0.0284 (10)0.0250 (9)0.0001 (8)0.0139 (8)0.0041 (8)
C230.0233 (10)0.0261 (10)0.0248 (9)0.0042 (8)0.0137 (8)0.0028 (8)
Geometric parameters (Å, º) top
Zn1—O41.9505 (13)O5—C151.237 (2)
Zn1—O32.0277 (14)N5—C131.492 (2)
Zn1—OW12.0412 (14)O6—C231.228 (3)
Zn1—OW22.0501 (14)C6—C71.407 (3)
Zn1—O12.0553 (15)C6—H6A0.9300
O1—C11.255 (2)O7—C231.271 (2)
OW1—HW1A0.8193C7—C81.439 (3)
OW1—HW1B0.8271O8—C221.210 (2)
N1—C101.475 (3)O9—C221.310 (2)
N1—C111.503 (3)O9—H9A0.8547
N1—H1A0.9000C9—C101.515 (3)
N1—H1B0.8999C9—H9B0.9700
C1—O21.255 (2)C9—H9C0.9700
C1—C21.505 (3)C10—H10A0.9700
OW2—HW2A0.8247C10—H10B0.9700
OW2—HW2B0.8319C11—C121.506 (3)
N2—C51.343 (2)C11—H11A0.9700
N2—C121.460 (3)C11—H11B0.9700
N2—C91.468 (3)C12—H12A0.9700
C2—C31.368 (3)C12—H12B0.9700
C2—C81.431 (3)C13—C141.477 (3)
C2O—C191.386 (3)C13—H13A0.9700
C2O—C211.396 (3)C13—H13B0.9700
C2O—C221.504 (3)C14—H14A0.9600
OW3—HW3A0.8383C14—H14B0.9600
OW3—HW3B0.8382C14—H14C0.9600
O3—C81.275 (2)C15—C161.506 (2)
N3—C61.312 (3)C16—C211.385 (3)
N3—C51.376 (2)C16—C171.398 (3)
C3—N51.341 (2)C17—C181.399 (3)
C3—H3A0.9300C17—H17A0.9300
O4—C151.272 (2)C18—C191.393 (3)
N4—C41.336 (2)C18—C231.519 (3)
N4—C51.338 (2)C19—H19A0.9300
C4—N51.381 (2)C21—H21A0.9300
C4—C71.405 (3)
O4—Zn1—O3131.63 (6)C22—O9—H9A107.1
O4—Zn1—OW1106.43 (6)N2—C9—C10110.23 (17)
O3—Zn1—OW1121.73 (6)N2—C9—H9B109.6
O4—Zn1—OW298.83 (6)C10—C9—H9B109.6
O3—Zn1—OW287.86 (6)N2—C9—H9C109.6
OW1—Zn1—OW287.92 (6)C10—C9—H9C109.6
O4—Zn1—O190.56 (6)H9B—C9—H9C108.1
O3—Zn1—O185.95 (6)N1—C10—C9111.33 (16)
OW1—Zn1—O189.35 (6)N1—C10—H10A109.4
OW2—Zn1—O1170.62 (6)C9—C10—H10A109.4
C1—O1—Zn1131.15 (13)N1—C10—H10B109.4
Zn1—OW1—HW1A109.7C9—C10—H10B109.4
Zn1—OW1—HW1B118.8H10A—C10—H10B108.0
HW1A—OW1—HW1B114.6N1—C11—C12111.01 (18)
C10—N1—C11114.71 (17)N1—C11—H11A109.4
C10—N1—H1A108.6C12—C11—H11A109.4
C11—N1—H1A108.5N1—C11—H11B109.4
C10—N1—H1B108.6C12—C11—H11B109.4
C11—N1—H1B108.6H11A—C11—H11B108.0
H1A—N1—H1B107.6N2—C12—C11110.94 (18)
O1—C1—O2122.04 (18)N2—C12—H12A109.5
O1—C1—C2119.83 (17)C11—C12—H12A109.5
O2—C1—C2118.10 (17)N2—C12—H12B109.5
Zn1—OW2—HW2A116.8C11—C12—H12B109.5
Zn1—OW2—HW2B118.8H12A—C12—H12B108.0
HW2A—OW2—HW2B111.3C14—C13—N5112.67 (19)
C5—N2—C12122.99 (16)C14—C13—H13A109.1
C5—N2—C9119.84 (16)N5—C13—H13A109.1
C12—N2—C9117.14 (16)C14—C13—H13B109.1
C3—C2—C8118.77 (17)N5—C13—H13B109.1
C3—C2—C1117.39 (16)H13A—C13—H13B107.8
C8—C2—C1123.80 (16)C13—C14—H14A109.5
C19—C2O—C21119.41 (17)C13—C14—H14B109.5
C19—C2O—C22121.32 (16)H14A—C14—H14B109.5
C21—C2O—C22119.19 (17)C13—C14—H14C109.5
HW3A—OW3—HW3B109.4H14A—C14—H14C109.5
C8—O3—Zn1128.01 (13)H14B—C14—H14C109.5
C6—N3—C5115.66 (16)O5—C15—O4123.77 (17)
N5—C3—C2125.35 (17)O5—C15—C16121.28 (16)
N5—C3—H3A117.3O4—C15—C16114.94 (16)
C2—C3—H3A117.3C21—C16—C17119.49 (17)
C15—O4—Zn1120.47 (12)C21—C16—C15117.82 (17)
C4—N4—C5116.09 (16)C17—C16—C15122.66 (17)
N4—C4—N5117.77 (16)C16—C17—C18120.43 (17)
N4—C4—C7123.49 (17)C16—C17—H17A119.8
N5—C4—C7118.74 (16)C18—C17—H17A119.8
C3—N5—C4119.24 (15)C19—C18—C17118.99 (17)
C3—N5—C13119.27 (16)C19—C18—C23120.31 (16)
C4—N5—C13121.39 (16)C17—C18—C23120.61 (16)
N4—C5—N2117.45 (17)C2O—C19—C18120.99 (17)
N4—C5—N3125.89 (17)C2O—C19—H19A119.5
N2—C5—N3116.65 (17)C18—C19—H19A119.5
N3—C6—C7124.19 (17)C16—C21—C2O120.65 (17)
N3—C6—H6A117.9C16—C21—H21A119.7
C7—C6—H6A117.9C2O—C21—H21A119.7
C4—C7—C6114.51 (17)O8—C22—O9124.50 (18)
C4—C7—C8122.25 (17)O8—C22—C2O122.69 (18)
C6—C7—C8123.24 (17)O9—C22—C2O112.82 (16)
O3—C8—C2125.06 (18)O6—C23—O7124.09 (19)
O3—C8—C7119.38 (17)O6—C23—C18119.57 (17)
C2—C8—C7115.56 (16)O7—C23—C18116.33 (17)
O4—Zn1—O1—C1157.90 (19)C3—C2—C8—O3179.39 (18)
O3—Zn1—O1—C126.19 (18)C1—C2—C8—O33.1 (3)
OW1—Zn1—O1—C195.68 (19)C3—C2—C8—C70.5 (2)
OW2—Zn1—O1—C122.6 (5)C1—C2—C8—C7176.99 (16)
Zn1—O1—C1—O2163.93 (14)C4—C7—C8—O3177.04 (17)
Zn1—O1—C1—C217.9 (3)C6—C7—C8—O33.5 (3)
O1—C1—C2—C3179.80 (18)C4—C7—C8—C22.8 (2)
O2—C1—C2—C31.6 (3)C6—C7—C8—C2176.66 (16)
O1—C1—C2—C82.3 (3)C5—N2—C9—C10166.77 (17)
O2—C1—C2—C8175.91 (17)C12—N2—C9—C1011.2 (3)
O4—Zn1—O3—C8111.22 (16)C11—N1—C10—C956.9 (2)
OW1—Zn1—O3—C862.65 (17)N2—C9—C10—N144.5 (2)
OW2—Zn1—O3—C8148.87 (16)C10—N1—C11—C1211.1 (3)
O1—Zn1—O3—C824.08 (16)C5—N2—C12—C11120.9 (2)
C8—C2—C3—N51.2 (3)C9—N2—C12—C1157.0 (2)
C1—C2—C3—N5178.84 (17)N1—C11—C12—N243.3 (2)
O3—Zn1—O4—C152.41 (18)C3—N5—C13—C1479.6 (2)
OW1—Zn1—O4—C15172.16 (14)C4—N5—C13—C14104.1 (2)
OW2—Zn1—O4—C1597.42 (14)Zn1—O4—C15—O517.8 (2)
O1—Zn1—O4—C1582.66 (15)Zn1—O4—C15—C16162.60 (12)
C5—N4—C4—N5178.14 (15)O5—C15—C16—C21174.32 (17)
C5—N4—C4—C70.8 (3)O4—C15—C16—C216.1 (2)
C2—C3—N5—C40.5 (3)O5—C15—C16—C177.8 (3)
C2—C3—N5—C13176.88 (18)O4—C15—C16—C17171.76 (16)
N4—C4—N5—C3179.16 (16)C21—C16—C17—C181.0 (3)
C7—C4—N5—C31.8 (2)C15—C16—C17—C18176.78 (16)
N4—C4—N5—C134.6 (2)C16—C17—C18—C192.4 (3)
C7—C4—N5—C13174.43 (16)C16—C17—C18—C23173.99 (16)
C4—N4—C5—N2177.05 (16)C21—C2O—C19—C180.2 (3)
C4—N4—C5—N33.2 (3)C22—C2O—C19—C18176.69 (16)
C12—N2—C5—N4179.90 (17)C17—C18—C19—C2O2.0 (3)
C9—N2—C5—N42.1 (3)C23—C18—C19—C2O174.44 (16)
C12—N2—C5—N30.3 (3)C17—C16—C21—C2O0.8 (3)
C9—N2—C5—N3178.13 (16)C15—C16—C21—C2O178.74 (16)
C6—N3—C5—N44.5 (3)C19—C2O—C21—C161.3 (3)
C6—N3—C5—N2175.71 (17)C22—C2O—C21—C16178.18 (16)
C5—N3—C6—C71.9 (3)C19—C2O—C22—O82.0 (3)
N4—C4—C7—C63.0 (3)C21—C2O—C22—O8178.81 (18)
N5—C4—C7—C6175.96 (16)C19—C2O—C22—O9177.94 (16)
N4—C4—C7—C8177.49 (16)C21—C2O—C22—O91.1 (2)
N5—C4—C7—C83.6 (3)C19—C18—C23—O6160.80 (19)
N3—C6—C7—C41.5 (3)C17—C18—C23—O615.6 (3)
N3—C6—C7—C8178.97 (17)C19—C18—C23—O718.2 (3)
Zn1—O3—C8—C215.8 (3)C17—C18—C23—O7165.44 (16)
Zn1—O3—C8—C7164.05 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.901.962.821 (2)160
N1—H1B···O8ii0.902.202.930 (2)138
O9—H9A···O7iii0.851.762.5722 (19)158
OW1—HW1A···O5ii0.821.832.647 (2)176
OW2—HW2A···O6ii0.821.852.674 (2)174
OW3—HW3A···O3iv0.842.272.977 (2)142
OW3—HW3B···OW1v0.842.373.159 (2)156
OW2—HW2B···O2vi0.831.892.715 (2)169
Symmetry codes: (i) x+1, y, z; (ii) x, y1/2, z+1/2; (iii) x1, y1/2, z+1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1/2, z+1/2; (vi) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.901.962.821 (2)159.7
N1—H1B···O8ii0.902.202.930 (2)137.7
O9—H9A···O7iii0.851.762.5722 (19)158.4
OW1—HW1A···O5ii0.821.832.647 (2)175.6
OW2—HW2A···O6ii0.821.852.674 (2)174.0
OW3—HW3A···O3iv0.842.272.977 (2)141.5
OW3—HW3B···OW1v0.842.373.159 (2)156.2
OW2—HW2B···O2vi0.831.892.715 (2)169.4
Symmetry codes: (i) x+1, y, z; (ii) x, y1/2, z+1/2; (iii) x1, y1/2, z+1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1/2, z+1/2; (vi) x, y+1/2, z+1/2.
Acknowledgements top

This work was supported financially by the Science and Technology Foundation of Southwest University (grant No. SWUB2007035) and the Science and Technology Innovation Foundation for Students of Southwest University.

references
References top

Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37, Suppl. A, 41–45.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Zhang, G.-J., He, J.-H., Yan, S.-W., Ye, Z.-L. & Xin, G.-H. (2011). Acta Cryst. E67, o1011–o1012.