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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): m804.
Published online 2010 June 16. doi:  10.1107/S1600536810021641
PMCID: PMC3006871

Hexaaqua­zinc(II) bis­(2,4,5-tricarboxybenzoate) 4,5-diaza­fluoren-9-one disolvate dihydrate

Abstract

The asymmetric unit of the title complex, [Zn(H2O)6](C10H5O8)2·2C11H6N2O·2H2O, contains one half of the complex cation with the ZnII ion located on an inversion center, a monovalent 2,4,5-tricarboxybenzoate (1,2,4,5-BTC) counter-anion, a 4,5-diaza­fluoren-9-one (DAFO) mol­ecule and an uncoordinated water mol­ecule. In the crystal structure, O—H(...)O and O—H(...)N hydrogen bonds link the cations, anions and water mol­ecules into a three-dimensional network.

Related literature

For ZnII complexes, see: Rochon & Massarweh (2000 [triangle]); Si et al. (2003 [triangle]). For a related structure, see: Zhu et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m804-scheme1.jpg

Experimental

Crystal data

  • [Zn(H2O)6](C10H5O8)2·2C11H6N2O·2H2O
  • M r = 1080.13
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m804-efi1.jpg
  • a = 8.380 (5) Å
  • b = 9.757 (5) Å
  • c = 14.107 (5) Å
  • α = 77.964 (5)°
  • β = 77.709 (5)°
  • γ = 89.948 (5)°
  • V = 1101.1 (9) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.66 mm−1
  • T = 293 K
  • 0.28 × 0.23 × 0.19 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.836, T max = 0.885
  • 6855 measured reflections
  • 5060 independent reflections
  • 4670 reflections with I > 2σ(I)
  • R int = 0.014

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.086
  • S = 1.06
  • 5060 reflections
  • 343 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021641/er2077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021641/er2077Isup2.hkl

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

Acknowledgments

The authors thank the National Natural Science Foundation of China (No. 50878041) and the Analysis and Testing Foundation of Northeast Normal University for financial support.

supplementary crystallographic information

Comment

Single-crystal X-ray diffraction analyses revealed ZnII is hexa-coordinated and exhibits octahedral coordintion environment supplied by six water molecules (Fig. 1). The O atoms from four coordinated water molecules in the equatorial plane around the ZnII ion form a slightly distorted square-planar arrangement with an average Zn—O bond length of 2.073 (1) Å; the slightly distorted octahedral coordination is completed by the other O atoms at a slightly shorter distance [2.055 (2) Å] in the axial positions. benzene-1,2,4,5-tetracarboxylate (1,2,4,5-BTC) counter-anion, and DAFO molecule are both uncoordinated. Intermolecular hydrogen bonds, O—H···O and O—H···N, extend the ion complex into a three-dimensional supramolecular network structure (Fig. 2, Table 1).

Experimental

Zinc(II) acetate dihydrate (0.066 g, 0.3 mol), benzene-1,2,4,5-tetracarboxylate (0.055 g, 0.2 mmol), 4, 5-diazafluoren-9-one (0.036 g, 0.2 mmol), sodium hydroxide (0.016 g, 0.4 mmol) and water (14 ml) were placed in a 23 ml Teflon-lined autoclave, and the autoclave was heated at 423 K for 3 d. After cooling slowly to room temperature at a rate of 10 K h-1, colorless crystals were obtained.

Refinement

C-bound H atoms were treated as riding, with C—H = 0.93Å and Uiso(H) = 1.2 times Ueq(C). O-bound H atoms were located in a difference Fourier map and refined as riding in their as-found relative positions; Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
View of the local coordination of ZnII with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A packing diagram for the three-dimensional supramolecular framework via O—H···O interactions. The view direction is parallel to the a axis. Hydrogen bonds are indicated by dashed lines.

Crystal data

[Zn(H2O)6](C10H5O8)2·2C11H6N2O·2H2OZ = 1
Mr = 1080.13F(000) = 556
Triclinic, P1Dx = 1.629 Mg m3
a = 8.380 (5) ÅMo Kα radiation, λ = 0.71069 Å
b = 9.757 (5) ÅCell parameters from 6265 reflections
c = 14.107 (5) Åθ = 2.1–28.2°
α = 77.964 (5)°µ = 0.66 mm1
β = 77.709 (5)°T = 293 K
γ = 89.948 (5)°Block, colorless
V = 1101.1 (9) Å30.28 × 0.23 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer5060 independent reflections
Radiation source: fine-focus sealed tube4670 reflections with I > 2σ(I)
graphiteRint = 0.014
Detector resolution: 10 pixels mm-1θmax = 28.3°, θmin = 1.5°
ω scanh = −11→4
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −12→12
Tmin = 0.836, Tmax = 0.885l = −18→16
6855 measured reflections

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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0461P)2 + 0.2811P] where P = (Fo2 + 2Fc2)/3
5060 reflections(Δ/σ)max = 0.001
343 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = −0.34 e Å3

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
Zn10.00000.50000.50000.02688 (8)
O10.70290 (17)0.59156 (12)0.76405 (8)0.0414 (3)
O20.64715 (15)0.36226 (11)0.82062 (9)0.0356 (2)
O30.89652 (15)0.20199 (11)0.90798 (9)0.0374 (3)
O40.68585 (18)0.13427 (11)1.03103 (9)0.0510 (4)
O50.72889 (14)0.45006 (13)1.28469 (8)0.0394 (3)
O60.93948 (14)0.60062 (13)1.21458 (8)0.0371 (3)
O70.68773 (16)0.79402 (12)1.15402 (8)0.0408 (3)
O80.7470 (2)0.88143 (12)0.99083 (9)0.0521 (4)
O120.55282 (18)0.75220 (15)0.47805 (12)0.0579 (4)
N10.76786 (17)1.09551 (14)0.61753 (10)0.0354 (3)
N20.93283 (18)1.14163 (15)0.39355 (10)0.0372 (3)
C10.72961 (16)0.49108 (14)0.92716 (10)0.0235 (3)
C20.76421 (17)0.37449 (13)0.99478 (10)0.0241 (3)
C30.78982 (18)0.39158 (14)1.08567 (10)0.0269 (3)
H30.81150.31361.13090.032*
C40.78401 (16)0.52197 (14)1.11107 (10)0.0239 (3)
C50.74847 (17)0.63815 (13)1.04361 (10)0.0240 (3)
C60.72178 (17)0.62128 (14)0.95285 (10)0.0254 (3)
H60.69810.69900.90820.030*
C70.69319 (17)0.48682 (14)0.82862 (10)0.0267 (3)
C80.77793 (19)0.22755 (14)0.97678 (10)0.0293 (3)
C90.81864 (17)0.52666 (14)1.21153 (10)0.0260 (3)
C100.72500 (18)0.77881 (14)1.07017 (11)0.0280 (3)
C110.6757 (2)1.05207 (18)0.71039 (13)0.0422 (4)
H110.68901.10190.75790.051*
C120.5640 (2)0.9399 (2)0.74011 (14)0.0462 (4)
H120.50470.91660.80540.055*
C130.5404 (2)0.86182 (18)0.67221 (14)0.0432 (4)
H130.46650.78500.69000.052*
C140.63219 (19)0.90423 (16)0.57714 (13)0.0349 (3)
C150.6374 (2)0.84773 (18)0.48618 (14)0.0401 (4)
C160.7622 (2)0.93733 (17)0.40690 (13)0.0371 (3)
C170.8169 (2)0.9358 (2)0.30764 (14)0.0477 (4)
H170.77870.86770.27960.057*
C180.9305 (3)1.0392 (2)0.25193 (14)0.0503 (5)
H180.97101.04210.18480.060*
C190.9840 (2)1.1388 (2)0.29631 (13)0.0456 (4)
H191.06001.20810.25690.055*
C200.82315 (18)1.04143 (15)0.44622 (12)0.0315 (3)
C210.74262 (18)1.01997 (15)0.55338 (11)0.0304 (3)
O1W0.54813 (14)0.40373 (14)0.64908 (9)0.0427 (3)
H1A0.50310.33050.63880.064*
H1B0.46920.46120.66580.064*
O90.21520 (14)0.55344 (16)0.53380 (9)0.0485 (3)
H9A0.29060.55610.49350.073*
H9B0.23080.55490.58950.073*
O10−0.11749 (14)0.65168 (12)0.56875 (8)0.0378 (3)
H10A−0.17230.62860.62590.057*
H11B−0.09870.27350.62400.057*
O11−0.06978 (15)0.34898 (12)0.63034 (8)0.0389 (3)
H11A−0.02260.34590.67090.058*
H10B−0.05020.71560.57570.058*
H3O0.957 (3)0.281 (3)0.865 (2)0.083 (9)*
H2O0.629 (3)0.369 (3)0.7620 (19)0.063 (7)*
H8O0.732 (3)0.959 (3)1.0088 (19)0.071 (8)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.03260 (13)0.02768 (13)0.02240 (12)0.00010 (9)−0.00775 (9)−0.00810 (9)
O10.0733 (8)0.0291 (6)0.0246 (5)0.0058 (5)−0.0168 (5)−0.0054 (4)
O20.0530 (7)0.0292 (5)0.0304 (6)−0.0027 (5)−0.0169 (5)−0.0114 (4)
O30.0468 (6)0.0257 (5)0.0383 (6)0.0047 (5)0.0001 (5)−0.0130 (5)
O40.0778 (9)0.0201 (5)0.0433 (7)−0.0077 (5)0.0147 (6)−0.0091 (5)
O50.0452 (6)0.0485 (7)0.0221 (5)−0.0104 (5)−0.0067 (4)−0.0030 (5)
O60.0418 (6)0.0449 (6)0.0264 (5)−0.0096 (5)−0.0109 (4)−0.0080 (5)
O70.0630 (8)0.0324 (6)0.0323 (6)0.0055 (5)−0.0105 (5)−0.0182 (5)
O80.1023 (11)0.0172 (5)0.0347 (6)0.0055 (6)−0.0075 (7)−0.0088 (5)
O120.0530 (8)0.0509 (8)0.0825 (11)−0.0060 (6)−0.0266 (7)−0.0304 (7)
N10.0454 (7)0.0281 (6)0.0353 (7)0.0025 (5)−0.0097 (6)−0.0120 (5)
N20.0451 (7)0.0342 (7)0.0343 (7)0.0042 (6)−0.0091 (6)−0.0114 (5)
C10.0307 (6)0.0199 (6)0.0202 (6)0.0004 (5)−0.0046 (5)−0.0060 (5)
C20.0326 (7)0.0175 (6)0.0224 (6)0.0002 (5)−0.0041 (5)−0.0065 (5)
C30.0387 (7)0.0195 (6)0.0227 (6)0.0041 (5)−0.0080 (5)−0.0034 (5)
C40.0293 (6)0.0231 (6)0.0200 (6)0.0007 (5)−0.0053 (5)−0.0066 (5)
C50.0322 (7)0.0189 (6)0.0221 (6)0.0007 (5)−0.0053 (5)−0.0077 (5)
C60.0370 (7)0.0187 (6)0.0210 (6)0.0027 (5)−0.0071 (5)−0.0045 (5)
C70.0333 (7)0.0259 (7)0.0227 (7)0.0036 (5)−0.0059 (5)−0.0098 (5)
C80.0452 (8)0.0177 (6)0.0257 (7)0.0021 (5)−0.0066 (6)−0.0072 (5)
C90.0330 (7)0.0258 (6)0.0219 (6)0.0045 (5)−0.0081 (5)−0.0089 (5)
C100.0378 (7)0.0200 (6)0.0281 (7)0.0012 (5)−0.0077 (6)−0.0091 (5)
C110.0540 (10)0.0377 (9)0.0363 (9)0.0072 (7)−0.0071 (7)−0.0140 (7)
C120.0472 (10)0.0423 (9)0.0427 (10)0.0068 (7)0.0013 (7)−0.0061 (7)
C130.0366 (8)0.0335 (8)0.0564 (11)0.0027 (6)−0.0066 (7)−0.0062 (7)
C140.0323 (7)0.0285 (7)0.0480 (9)0.0064 (6)−0.0134 (6)−0.0127 (6)
C150.0373 (8)0.0347 (8)0.0584 (11)0.0077 (6)−0.0223 (7)−0.0204 (7)
C160.0394 (8)0.0374 (8)0.0447 (9)0.0100 (6)−0.0205 (7)−0.0199 (7)
C170.0554 (11)0.0535 (11)0.0506 (11)0.0162 (9)−0.0277 (9)−0.0311 (9)
C180.0615 (12)0.0607 (12)0.0353 (9)0.0172 (9)−0.0156 (8)−0.0203 (8)
C190.0546 (10)0.0469 (10)0.0351 (9)0.0076 (8)−0.0080 (7)−0.0099 (7)
C200.0364 (7)0.0280 (7)0.0360 (8)0.0087 (6)−0.0145 (6)−0.0131 (6)
C210.0337 (7)0.0255 (7)0.0355 (8)0.0073 (5)−0.0111 (6)−0.0108 (6)
O1W0.0379 (6)0.0548 (7)0.0407 (7)0.0006 (5)−0.0088 (5)−0.0221 (6)
O90.0346 (6)0.0857 (10)0.0278 (6)−0.0111 (6)−0.0068 (5)−0.0177 (6)
O100.0448 (6)0.0351 (6)0.0336 (6)0.0016 (5)−0.0024 (5)−0.0140 (5)
O110.0550 (7)0.0349 (6)0.0283 (6)−0.0069 (5)−0.0156 (5)−0.0031 (4)

Geometric parameters (Å, °)

Zn1—O9i2.0550 (15)C4—C91.5156 (19)
Zn1—O92.0550 (15)C5—C61.3879 (19)
Zn1—O10i2.0712 (13)C5—C101.4983 (19)
Zn1—O102.0712 (13)C6—H60.9300
Zn1—O11i2.0755 (12)C11—C121.376 (3)
Zn1—O112.0755 (12)C11—H110.9300
O1—C71.2088 (18)C12—C131.386 (3)
O2—C71.3097 (18)C12—H120.9300
O2—H2O0.86 (3)C13—C141.375 (3)
O3—C81.2968 (18)C13—H130.9300
O3—H3O0.94 (3)C14—C211.399 (2)
O4—C81.2119 (19)C14—C151.491 (2)
O5—C91.2402 (18)C15—C161.485 (3)
O6—C91.2573 (19)C16—C171.381 (3)
O7—C101.1978 (18)C16—C201.399 (2)
O8—C101.3169 (19)C17—C181.376 (3)
O8—H8O0.85 (3)C17—H170.9300
O12—C151.210 (2)C18—C191.383 (3)
N1—C211.329 (2)C18—H180.9300
N1—C111.353 (2)C19—H190.9300
N2—C201.327 (2)C20—C211.489 (2)
N2—C191.354 (2)O1W—H1A0.8602
C1—C61.3897 (19)O1W—H1B0.8916
C1—C21.3974 (19)O9—H9A0.7509
C1—C71.4939 (19)O9—H9B0.8266
C2—C31.3871 (19)O10—H10A0.8240
C2—C81.5075 (19)O10—H10B0.8756
C3—C41.390 (2)O11—H11B0.8033
C3—H30.9300O11—H11A0.7581
C4—C51.3962 (19)
O9i—Zn1—O9180.00 (6)O7—C10—O8124.78 (13)
O9i—Zn1—O10i90.19 (6)O7—C10—C5123.23 (13)
O9—Zn1—O10i89.81 (6)O8—C10—C5111.97 (12)
O9i—Zn1—O1089.81 (6)N1—C11—C12125.12 (17)
O9—Zn1—O1090.19 (6)N1—C11—H11117.4
O10i—Zn1—O10180.000 (1)C12—C11—H11117.4
O9i—Zn1—O11i93.35 (5)C11—C12—C13119.65 (17)
O9—Zn1—O11i86.65 (5)C11—C12—H12120.2
O10i—Zn1—O11i90.77 (6)C13—C12—H12120.2
O10—Zn1—O11i89.23 (6)C14—C13—C12116.35 (16)
O9i—Zn1—O1186.65 (5)C14—C13—H13121.8
O9—Zn1—O1193.35 (5)C12—C13—H13121.8
O10i—Zn1—O1189.23 (6)C13—C14—C21120.15 (15)
O10—Zn1—O1190.77 (6)C13—C14—C15131.05 (16)
O11i—Zn1—O11180.0C21—C14—C15108.79 (15)
C7—O2—H2O108.3 (17)O12—C15—C16127.32 (18)
C8—O3—H3O116.1 (17)O12—C15—C14126.97 (18)
C10—O8—H8O109.1 (18)C16—C15—C14105.65 (13)
C21—N1—C11114.33 (14)C17—C16—C20119.59 (17)
C20—N2—C19115.56 (15)C17—C16—C15131.56 (16)
C6—C1—C2119.02 (12)C20—C16—C15108.80 (15)
C6—C1—C7116.07 (12)C18—C17—C16117.23 (17)
C2—C1—C7124.86 (12)C18—C17—H17121.4
C3—C2—C1119.25 (12)C16—C17—H17121.4
C3—C2—C8115.88 (12)C17—C18—C19119.64 (17)
C1—C2—C8124.87 (12)C17—C18—H18120.2
C2—C3—C4121.84 (12)C19—C18—H18120.2
C2—C3—H3119.1N2—C19—C18124.07 (18)
C4—C3—H3119.1N2—C19—H19118.0
C3—C4—C5118.79 (12)C18—C19—H19118.0
C3—C4—C9116.48 (12)N2—C20—C16123.90 (15)
C5—C4—C9124.73 (12)N2—C20—C21127.60 (14)
C6—C5—C4119.52 (12)C16—C20—C21108.50 (14)
C6—C5—C10118.91 (12)N1—C21—C14124.40 (15)
C4—C5—C10121.39 (12)N1—C21—C20127.36 (14)
C5—C6—C1121.57 (12)C14—C21—C20108.24 (13)
C5—C6—H6119.2H1A—O1W—H1B107.9
C1—C6—H6119.2Zn1—O9—H9A115.7
O1—C7—O2124.26 (14)Zn1—O9—H9B126.9
O1—C7—C1121.57 (13)H9A—O9—H9B115.9
O2—C7—C1114.14 (12)Zn1—O10—H10A119.5
O4—C8—O3121.35 (13)Zn1—O10—H10B113.2
O4—C8—C2119.60 (13)H10A—O10—H10B100.6
O3—C8—C2118.84 (12)Zn1—O11—H11B115.8
O5—C9—O6124.96 (13)Zn1—O11—H11A119.0
O5—C9—C4116.40 (13)H11B—O11—H11A114.1
O6—C9—C4118.52 (12)
C6—C1—C2—C30.0 (2)N1—C11—C12—C130.3 (3)
C7—C1—C2—C3−177.52 (13)C11—C12—C13—C14−0.5 (3)
C6—C1—C2—C8−179.46 (13)C12—C13—C14—C210.3 (2)
C7—C1—C2—C83.0 (2)C12—C13—C14—C15−179.10 (16)
C1—C2—C3—C4−0.8 (2)C13—C14—C15—O123.2 (3)
C8—C2—C3—C4178.71 (13)C21—C14—C15—O12−176.28 (17)
C2—C3—C4—C51.2 (2)C13—C14—C15—C16−179.47 (17)
C2—C3—C4—C9−178.42 (13)C21—C14—C15—C161.10 (17)
C3—C4—C5—C6−0.7 (2)O12—C15—C16—C17−1.6 (3)
C9—C4—C5—C6178.82 (13)C14—C15—C16—C17−178.92 (17)
C3—C4—C5—C10174.23 (13)O12—C15—C16—C20175.75 (17)
C9—C4—C5—C10−6.2 (2)C14—C15—C16—C20−1.62 (17)
C4—C5—C6—C10.0 (2)C20—C16—C17—C18−0.2 (2)
C10—C5—C6—C1−175.12 (13)C15—C16—C17—C18176.91 (18)
C2—C1—C6—C50.4 (2)C16—C17—C18—C19−0.2 (3)
C7—C1—C6—C5178.14 (12)C20—N2—C19—C18−0.7 (3)
C6—C1—C7—O120.5 (2)C17—C18—C19—N20.6 (3)
C2—C1—C7—O1−161.92 (15)C19—N2—C20—C160.4 (2)
C6—C1—C7—O2−157.94 (13)C19—N2—C20—C21−178.61 (15)
C2—C1—C7—O219.6 (2)C17—C16—C20—N20.0 (2)
C3—C2—C8—O461.2 (2)C15—C16—C20—N2−177.65 (14)
C1—C2—C8—O4−119.33 (18)C17—C16—C20—C21179.20 (14)
C3—C2—C8—O3−113.59 (16)C15—C16—C20—C211.52 (17)
C1—C2—C8—O365.9 (2)C11—N1—C21—C14−0.4 (2)
C3—C4—C9—O5−57.77 (18)C11—N1—C21—C20179.48 (15)
C5—C4—C9—O5122.67 (16)C13—C14—C21—N10.2 (2)
C3—C4—C9—O6118.48 (15)C15—C14—C21—N1179.69 (14)
C5—C4—C9—O6−61.1 (2)C13—C14—C21—C20−179.72 (14)
C6—C5—C10—O7152.54 (15)C15—C14—C21—C20−0.21 (17)
C4—C5—C10—O7−22.5 (2)N2—C20—C21—N1−1.6 (3)
C6—C5—C10—O8−26.2 (2)C16—C20—C21—N1179.28 (15)
C4—C5—C10—O8158.82 (15)N2—C20—C21—C14178.31 (15)
C21—N1—C11—C120.2 (3)C16—C20—C21—C14−0.83 (17)

Symmetry codes: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1A···O12ii0.862.122.8342 (19)141
O1W—H1B···O5iii0.891.942.815 (2)168
O9—H9A···O1Wii0.752.132.8526 (19)161
O9—H9B···O5iii0.831.872.6929 (18)177
O10—H10A···O1iv0.821.962.7860 (18)174
O11—H11B···N1v0.802.102.880 (2)166
O11—H11A···O6iii0.762.052.7725 (17)160
O10—H10B···N2vi0.881.882.747 (2)171
O3—H3O···O6vii0.94 (3)1.55 (3)2.4883 (18)173 (3)
O2—H2O···O1W0.86 (3)1.83 (3)2.6747 (19)167 (2)
O8—H8O···O4viii0.85 (3)1.83 (3)2.670 (2)171 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ER2077).

References

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  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Si, S.-F., Wang, R.-J. & Li, Y.-D. (2003). Inorg. Chem. Commun.6, 1152–1155.
  • Zhu, Z.-B., Gao, S. & Ng, S. W. (2009). Acta Cryst. E65, m1345. [PMC free article] [PubMed]

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