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Acta Cryst. (2009). E65, o2456    [ doi:10.1107/S1600536809036253 ]

2,2'-[(4,6-Dinitro-1,3-phenylene)dioxy]diacetic acid hemihydrate

D.-S. Ma, X.-M. Zhang, H. Zhang, D. Mu and G.-F. Hou

Abstract top

The skeletons of both independent molecules of the carboxylic acid hemihydrate, C10H8N2O10·0.5H2O, are approximately planar [maximum deviations 0.642 (3) and 0.468 (1) Å]. The deviations arise from the twisting of the nitro groups with respect to the aromatic rings [dihedral angles = 3.24 (2) and 27.01 (1), and 7.87 (1) and 16.37 (2)° in the two molecules]. The crystal structure features intermolecular O-H...O hydrogen bonds, which the link the dicarboxylic acid and water molecules into a supramolecular layer network.

Comment top

Flexible aromatic carboxylic acid with oxygen is a kind of biological activity of the organic carboxylic acid, not only in agriculture, such as plant growth regulators and herbicides it is applied, but also it is important to the synthesis of some organic medicine centre body. Compared with other rigid carboxylic acid ligands, such flexible aromatic carboxylic acid have highly plasticity and spatial configuration of, so it provides a rich and colorful way to identify and assemble for constructing a novel topological network structure with the special physical and chemical properties (Coronado et al., 2000; Gao et al., 2006). In this paper, we report the synthesis and crystal structures of a new flexible aromatic carboxylic acid compound.

In the crystal structure, the skeletons of the two dicarboxylic acid molecules are all approximately co-planar with the largest deviation being 0.642 (3) Å, 0.4681 Å from O8 and O15 for molecule C1–C10 and molecule C11–C20, respectively (Figure 1). This deviations are caused by the twisting of the nitro groups with the benzene planes.

There are six symmetry-independent 'active' H atoms in the crystal structure, all of them participate in hydrogen bonds, which link the dicarboxylic acid and water molecules into a two-dimensional layer supramolecular network (Table 1, Figure 2).

Related literature top

For general background to the use of flexible aromatic carboxylic acid ligands, see: Coronado et al. (2000). For the synthesis and related structures, see: Gao et al. (2006)

Experimental top

The synthesis of target product is as follows: chlorine acetic acid (51.6 g, 0.54 mol), sodalye(21.8 g, 0.54 mol) were dissolved into 200 ml distilled water with stirring. The mixture was heated to refluxed for 6 h, then the pH value was adjusted to about 2.0 by using 3 M hydrochloric acid. After cooling to the room temperature, 10.8 g (27%) yellow precipitate was obtained. The 10.8 g above yellow product was dissolved into 100 ml concentrated sulfuric acid with stirring, and then the mixture of nitric acid (9.45 g, 0.15 mol) and sulfuric acid (20.58 g, 0.21 mol) was dropped into the above solution with keeping the reaction trmperature under 0 ° C for 1 h. The mixture was poured into 500 ml water solution. The crude product was recrystallized from 100 ml water solution, 4.2 g yellow needle crystal was obtained (30%).

Refinement top

H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methylene), and with Uiso(H) = 1.2Ueq(C). Water H atoms were initially located in a difference Fourier map, but they were treated as riding on their parent atoms with O—H = 0.85 Å and with with Uiso(H) = 1.5 Ueq(O). Carboxylic H atoms were found in a difference Fourier map, and refined with Uiso(H) = 1.5 Ueq(O).

Computing details top

Data collection: RAPID-AUTO (Rigaku 1998); cell refinement: RAPID-AUTO (Rigaku 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); 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. The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level for non-H atoms.
[Figure 2] Fig. 2. A partial packing view, showing the three-dimensional supramolecular network. Dashed lines indicate the hydrogen-bonding interactions and no involving H atoms have been omitted.
2,2'-[(4,6-Dinitro-1,3-phenylene)dioxy]diacetic acid hemihydrate top
Crystal data top
C10H8N2O10·0.5H2OF(000) = 1336
Mr = 325.19Dx = 1.668 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 13902 reflections
a = 7.3873 (15) Åθ = 3.0–27.4°
b = 25.918 (5) ŵ = 0.16 mm−1
c = 13.711 (3) ÅT = 291 K
β = 99.43 (3)°Block, colorless
V = 2589.7 (9) Å30.25 × 0.21 × 0.20 mm
Z = 8
Data collection top
Rigaku RAXIS-RAPID
diffractometer		4552 independent reflections
Radiation source: fine-focus sealed tube3197 reflections with I > 2σ(I)
graphiteRint = 0.046
ω scanθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −8→8
Tmin = 0.962, Tmax = 0.970k = −30→30
19619 measured reflectionsl = −16→16
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.099P)2 + 0.8965P]
where P = (Fo2 + 2Fc2)/3
4552 reflections(Δ/σ)max < 0.001
410 parametersΔρmax = 0.42 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C10H8N2O10·0.5H2OV = 2589.7 (9) Å3
Mr = 325.19Z = 8
Monoclinic, P21/nMo Kα radiation
a = 7.3873 (15) ŵ = 0.16 mm−1
b = 25.918 (5) ÅT = 291 K
c = 13.711 (3) Å0.25 × 0.21 × 0.20 mm
β = 99.43 (3)°
Data collection top
Rigaku RAXIS-RAPID
diffractometer		4552 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		3197 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.970Rint = 0.046
19619 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.172Δρmax = 0.42 e Å−3
S = 1.03Δρmin = −0.29 e Å−3
4552 reflectionsAbsolute structure: ?
410 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
C11.0310 (4)−0.05466 (12)0.0762 (2)0.0453 (7)
C20.8978 (5)−0.03824 (14)0.1436 (3)0.0567 (9)
H2A0.7756−0.03370.10620.068*
H2B0.8927−0.06390.19460.068*
C30.8704 (4)0.03522 (12)0.2451 (2)0.0424 (7)
C40.7138 (4)0.01642 (12)0.2754 (2)0.0455 (8)
H40.6713−0.01620.25480.055*
C50.6181 (4)0.04510 (11)0.3361 (2)0.0393 (7)
C60.6824 (4)0.09461 (11)0.3636 (2)0.0416 (7)
C70.8398 (4)0.11370 (11)0.3348 (2)0.0442 (7)
H70.88110.14660.35440.053*
C80.9353 (4)0.08438 (11)0.2776 (2)0.0415 (7)
C90.3957 (4)−0.02105 (11)0.3406 (3)0.0486 (8)
H9A0.4864−0.04760.36110.058*
H9B0.3611−0.02260.26930.058*
C100.2310 (4)−0.02900 (12)0.3895 (3)0.0481 (8)
C111.0980 (4)0.38191 (11)0.5469 (2)0.0425 (7)
C120.9397 (4)0.34925 (11)0.5686 (2)0.0423 (7)
H12A0.85600.36990.60000.051*
H12B0.87260.33490.50800.051*
C130.9082 (4)0.27089 (11)0.6568 (2)0.0358 (6)
C140.7269 (4)0.26400 (11)0.6126 (2)0.0368 (6)
H140.67590.28700.56360.044*
C150.6187 (3)0.22418 (10)0.6385 (2)0.0327 (6)
C160.6953 (4)0.19013 (10)0.7146 (2)0.0354 (6)
C170.8751 (4)0.19648 (11)0.7588 (2)0.0372 (7)
H170.92560.17370.80830.045*
C180.9820 (4)0.23571 (11)0.7313 (2)0.0370 (7)
C190.3662 (4)0.25045 (11)0.5203 (2)0.0385 (7)
H19A0.43910.25130.46760.046*
H19B0.36230.28500.54720.046*
C200.1761 (4)0.23215 (12)0.4812 (2)0.0433 (7)
N11.1037 (4)0.10698 (12)0.2527 (2)0.0560 (7)
N20.5870 (4)0.12895 (10)0.4221 (2)0.0542 (7)
N31.1684 (3)0.23969 (10)0.78400 (19)0.0430 (6)
N40.5927 (4)0.14953 (9)0.75239 (19)0.0444 (6)
O11.1678 (3)−0.03181 (8)0.06594 (18)0.0536 (6)
O20.9765 (3)−0.09865 (9)0.03349 (19)0.0604 (7)
H21.0469−0.1072−0.00410.091*
O30.9670 (3)0.00887 (9)0.18550 (19)0.0589 (7)
O40.1546 (4)−0.07382 (9)0.3654 (2)0.0720 (8)
H50.0629−0.07710.39140.108*
O50.1750 (3)0.00126 (10)0.4427 (2)0.0687 (8)
O60.4686 (3)0.02851 (8)0.36993 (17)0.0509 (6)
O71.1969 (5)0.08272 (13)0.2060 (3)0.1029 (12)
O81.1449 (5)0.14971 (13)0.2799 (4)0.1298 (17)
O90.6063 (5)0.17479 (10)0.4134 (3)0.0998 (12)
O100.4939 (4)0.11086 (10)0.4787 (3)0.0919 (11)
O111.2585 (3)0.36932 (9)0.56650 (17)0.0533 (6)
O121.0395 (3)0.42478 (9)0.5016 (2)0.0614 (7)
H121.12710.44100.48770.092*
O131.0174 (3)0.30879 (8)0.63347 (16)0.0463 (5)
O140.0992 (3)0.26513 (11)0.4130 (2)0.0704 (8)
H15−0.00880.25730.39540.106*
O150.1017 (3)0.19503 (9)0.5074 (2)0.0635 (7)
O160.4453 (2)0.21590 (7)0.59524 (14)0.0391 (5)
O171.2814 (3)0.26610 (9)0.75223 (18)0.0541 (6)
O181.2051 (3)0.21598 (11)0.86301 (18)0.0644 (7)
O190.4279 (4)0.14545 (11)0.7251 (2)0.0824 (9)
O200.6744 (4)0.12010 (10)0.8133 (2)0.0701 (7)
O210.1450 (4)0.08578 (9)0.5660 (2)0.0706 (8)
H210.17450.11460.54370.106*
H220.17440.06160.52980.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0422 (17)0.0467 (17)0.0464 (19)0.0058 (14)0.0056 (14)−0.0020 (15)
C20.050 (2)0.061 (2)0.064 (2)0.0008 (16)0.0214 (17)−0.0124 (18)
C30.0395 (16)0.0499 (17)0.0399 (17)0.0061 (13)0.0127 (14)0.0010 (14)
C40.0448 (18)0.0434 (17)0.0512 (19)−0.0052 (13)0.0161 (15)−0.0092 (14)
C50.0367 (16)0.0395 (16)0.0446 (17)−0.0044 (12)0.0150 (14)−0.0017 (13)
C60.0417 (17)0.0380 (16)0.0481 (18)−0.0023 (12)0.0164 (14)−0.0013 (13)
C70.0448 (17)0.0366 (15)0.0530 (19)−0.0034 (13)0.0137 (15)0.0028 (14)
C80.0369 (16)0.0439 (16)0.0450 (18)−0.0030 (12)0.0103 (14)0.0060 (14)
C90.0491 (18)0.0380 (16)0.063 (2)−0.0102 (14)0.0229 (16)−0.0099 (15)
C100.0440 (18)0.0471 (18)0.056 (2)−0.0073 (14)0.0173 (16)−0.0031 (16)
C110.0497 (19)0.0412 (16)0.0380 (17)0.0002 (14)0.0117 (14)−0.0012 (13)
C120.0350 (16)0.0485 (17)0.0439 (18)0.0029 (13)0.0076 (13)0.0062 (14)
C130.0329 (14)0.0438 (16)0.0311 (15)−0.0027 (12)0.0063 (12)−0.0004 (12)
C140.0311 (14)0.0457 (16)0.0323 (15)0.0034 (12)0.0018 (12)0.0060 (12)
C150.0294 (14)0.0392 (15)0.0288 (14)0.0033 (11)0.0026 (11)−0.0027 (12)
C160.0347 (15)0.0413 (15)0.0302 (15)−0.0010 (12)0.0054 (12)−0.0036 (12)
C170.0383 (16)0.0424 (16)0.0296 (15)0.0054 (13)0.0017 (12)0.0039 (12)
C180.0302 (14)0.0486 (17)0.0309 (15)0.0055 (12)0.0010 (12)−0.0008 (13)
C190.0275 (14)0.0447 (16)0.0423 (17)0.0020 (12)0.0024 (13)0.0064 (13)
C200.0322 (15)0.0522 (18)0.0440 (18)0.0007 (13)0.0018 (13)0.0071 (15)
N10.0427 (15)0.0607 (18)0.069 (2)−0.0023 (13)0.0232 (15)0.0033 (15)
N20.0590 (17)0.0394 (15)0.071 (2)−0.0066 (12)0.0303 (16)−0.0094 (14)
N30.0350 (13)0.0550 (16)0.0370 (15)0.0061 (12)−0.0002 (11)−0.0025 (12)
N40.0571 (17)0.0395 (14)0.0356 (14)0.0016 (12)0.0045 (12)0.0036 (11)
O10.0496 (14)0.0502 (13)0.0646 (16)0.0048 (11)0.0201 (12)−0.0022 (11)
O20.0475 (13)0.0690 (16)0.0656 (17)0.0010 (12)0.0125 (12)−0.0206 (13)
O30.0515 (14)0.0615 (14)0.0712 (17)−0.0060 (11)0.0322 (13)−0.0211 (12)
O40.0710 (17)0.0559 (15)0.100 (2)−0.0295 (12)0.0460 (16)−0.0189 (14)
O50.0614 (15)0.0644 (15)0.091 (2)−0.0169 (12)0.0435 (15)−0.0233 (14)
O60.0466 (12)0.0433 (12)0.0700 (16)−0.0127 (9)0.0306 (12)−0.0147 (11)
O70.089 (2)0.101 (2)0.139 (3)−0.0308 (18)0.079 (2)−0.030 (2)
O80.102 (3)0.082 (2)0.231 (5)−0.0489 (19)0.101 (3)−0.049 (3)
O90.141 (3)0.0386 (14)0.143 (3)−0.0031 (15)0.094 (3)−0.0108 (16)
O100.116 (2)0.0620 (16)0.120 (3)−0.0231 (16)0.084 (2)−0.0273 (16)
O110.0384 (13)0.0601 (14)0.0604 (15)−0.0059 (10)0.0056 (11)0.0149 (11)
O120.0579 (14)0.0512 (14)0.0796 (18)0.0063 (11)0.0249 (14)0.0197 (12)
O130.0321 (11)0.0547 (13)0.0513 (13)−0.0040 (9)0.0041 (9)0.0157 (10)
O140.0390 (13)0.0869 (18)0.0759 (18)−0.0118 (12)−0.0185 (13)0.0336 (15)
O150.0473 (14)0.0642 (15)0.0754 (18)−0.0129 (12)−0.0010 (12)0.0166 (13)
O160.0299 (10)0.0479 (11)0.0377 (11)−0.0010 (8)0.0006 (8)0.0080 (9)
O170.0318 (11)0.0679 (15)0.0616 (15)−0.0030 (10)0.0045 (11)0.0026 (12)
O180.0487 (14)0.0928 (19)0.0454 (14)0.0050 (13)−0.0107 (11)0.0178 (13)
O190.0506 (16)0.0870 (19)0.101 (2)−0.0264 (13)−0.0121 (15)0.0424 (17)
O200.0700 (17)0.0651 (15)0.0722 (18)−0.0028 (13)0.0029 (14)0.0330 (14)
O210.0716 (17)0.0585 (14)0.089 (2)−0.0213 (12)0.0331 (15)−0.0060 (14)
Geometric parameters (Å, °) top
C1—O11.199 (4)C13—C141.389 (4)
C1—O21.314 (4)C13—C181.410 (4)
C1—C21.517 (4)C14—C151.387 (4)
C2—O31.409 (4)C14—H140.9300
C2—H2A0.9700C15—O161.338 (3)
C2—H2B0.9700C15—C161.412 (4)
C3—O31.355 (3)C16—C171.376 (4)
C3—C41.380 (4)C16—N41.441 (4)
C3—C81.408 (4)C17—C181.377 (4)
C4—C51.392 (4)C17—H170.9300
C4—H40.9300C18—N31.450 (4)
C5—O61.337 (3)C19—O161.414 (3)
C5—C61.398 (4)C19—C201.496 (4)
C6—C71.379 (4)C19—H19A0.9700
C6—N21.455 (4)C19—H19B0.9700
C7—C81.369 (4)C20—O151.192 (4)
C7—H70.9300C20—O141.324 (4)
C8—N11.465 (4)N1—O81.192 (4)
C9—O61.425 (3)N1—O71.194 (4)
C9—C101.497 (4)N2—O91.205 (3)
C9—H9A0.9700N2—O101.213 (4)
C9—H9B0.9700N3—O171.214 (3)
C10—O51.190 (4)N3—O181.236 (3)
C10—O41.310 (4)N4—O201.216 (3)
C11—O111.217 (4)N4—O191.218 (4)
C11—O121.311 (4)O2—H20.8200
C11—C121.512 (4)O4—H50.8200
C12—O131.433 (3)O12—H120.8200
C12—H12A0.9700O14—H150.8200
C12—H12B0.9700O21—H210.8500
C13—O131.343 (3)O21—H220.8501
O1—C1—O2125.4 (3)C14—C13—C18117.6 (2)
O1—C1—C2125.2 (3)C15—C14—C13122.6 (3)
O2—C1—C2109.4 (3)C15—C14—H14118.7
O3—C2—C1105.3 (3)C13—C14—H14118.7
O3—C2—H2A110.7O16—C15—C14123.7 (2)
C1—C2—H2A110.7O16—C15—C16117.8 (2)
O3—C2—H2B110.7C14—C15—C16118.5 (2)
C1—C2—H2B110.7C17—C16—C15119.4 (2)
H2A—C2—H2B108.8C17—C16—N4117.1 (3)
O3—C3—C4123.6 (3)C15—C16—N4123.4 (2)
O3—C3—C8117.5 (3)C16—C17—C18121.6 (3)
C4—C3—C8118.9 (3)C16—C17—H17119.2
C3—C4—C5121.6 (3)C18—C17—H17119.2
C3—C4—H4119.2C17—C18—C13120.3 (3)
C5—C4—H4119.2C17—C18—N3117.2 (3)
O6—C5—C4124.4 (3)C13—C18—N3122.5 (3)
O6—C5—C6117.8 (2)O16—C19—C20108.1 (2)
C4—C5—C6117.9 (2)O16—C19—H19A110.1
C7—C6—C5121.2 (3)C20—C19—H19A110.1
C7—C6—N2116.4 (3)O16—C19—H19B110.1
C5—C6—N2122.4 (2)C20—C19—H19B110.1
C8—C7—C6120.2 (3)H19A—C19—H19B108.4
C8—C7—H7119.9O15—C20—O14124.6 (3)
C6—C7—H7119.9O15—C20—C19126.9 (3)
C7—C8—C3120.2 (3)O14—C20—C19108.5 (3)
C7—C8—N1116.7 (3)O8—N1—O7121.1 (3)
C3—C8—N1123.1 (3)O8—N1—C8118.8 (3)
O6—C9—C10107.2 (2)O7—N1—C8120.1 (3)
O6—C9—H9A110.3O9—N2—O10122.2 (3)
C10—C9—H9A110.3O9—N2—C6118.3 (3)
O6—C9—H9B110.3O10—N2—C6119.6 (3)
C10—C9—H9B110.3O17—N3—O18122.0 (3)
H9A—C9—H9B108.5O17—N3—C18120.9 (3)
O5—C10—O4124.1 (3)O18—N3—C18117.1 (3)
O5—C10—C9125.0 (3)O20—N4—O19121.0 (3)
O4—C10—C9110.9 (3)O20—N4—C16118.3 (3)
O11—C11—O12124.4 (3)O19—N4—C16120.7 (3)
O11—C11—C12124.3 (3)C1—O2—H2109.5
O12—C11—C12111.2 (3)C3—O3—C2119.4 (2)
O13—C12—C11106.7 (2)C10—O4—H5109.5
O13—C12—H12A110.4C5—O6—C9119.2 (2)
C11—C12—H12A110.4C11—O12—H12109.5
O13—C12—H12B110.4C13—O13—C12119.2 (2)
C11—C12—H12B110.4C20—O14—H15109.5
H12A—C12—H12B108.6C15—O16—C19118.2 (2)
O13—C13—C14124.3 (3)H21—O21—H22109.5
O13—C13—C18118.0 (2)
O1—C1—C2—O32.2 (5)O13—C13—C18—C17179.3 (2)
O2—C1—C2—O3−179.9 (3)C14—C13—C18—C17−0.6 (4)
O3—C3—C4—C5−179.4 (3)O13—C13—C18—N31.2 (4)
C8—C3—C4—C50.7 (5)C14—C13—C18—N3−178.7 (2)
C3—C4—C5—O6−178.2 (3)O16—C19—C20—O15−0.2 (5)
C3—C4—C5—C61.9 (5)O16—C19—C20—O14178.2 (3)
O6—C5—C6—C7177.5 (3)C7—C8—N1—O8−2.7 (5)
C4—C5—C6—C7−2.6 (5)C3—C8—N1—O8177.0 (4)
O6—C5—C6—N2−3.5 (5)C7—C8—N1—O7177.4 (4)
C4—C5—C6—N2176.4 (3)C3—C8—N1—O7−2.9 (5)
C5—C6—C7—C80.7 (5)C7—C6—N2—O925.6 (5)
N2—C6—C7—C8−178.4 (3)C5—C6—N2—O9−153.5 (4)
C6—C7—C8—C32.0 (5)C7—C6—N2—O10−153.2 (3)
C6—C7—C8—N1−178.3 (3)C5—C6—N2—O1027.7 (5)
O3—C3—C8—C7177.5 (3)C17—C18—N3—O17165.4 (3)
C4—C3—C8—C7−2.7 (5)C13—C18—N3—O17−16.5 (4)
O3—C3—C8—N1−2.2 (5)C17—C18—N3—O18−16.1 (4)
C4—C3—C8—N1177.6 (3)C13—C18—N3—O18162.1 (3)
O6—C9—C10—O50.0 (5)C17—C16—N4—O20−7.4 (4)
O6—C9—C10—O4179.4 (3)C15—C16—N4—O20175.1 (3)
O11—C11—C12—O1312.5 (4)C17—C16—N4—O19171.4 (3)
O12—C11—C12—O13−169.4 (3)C15—C16—N4—O19−6.1 (4)
O13—C13—C14—C15179.7 (3)C4—C3—O3—C26.2 (5)
C18—C13—C14—C15−0.4 (4)C8—C3—O3—C2−174.0 (3)
C13—C14—C15—O16−178.2 (2)C1—C2—O3—C3175.8 (3)
C13—C14—C15—C161.5 (4)C4—C5—O6—C9−2.1 (5)
O16—C15—C16—C17178.0 (2)C6—C5—O6—C9177.8 (3)
C14—C15—C16—C17−1.7 (4)C10—C9—O6—C5179.9 (3)
O16—C15—C16—N4−4.5 (4)C14—C13—O13—C128.7 (4)
C14—C15—C16—N4175.7 (2)C18—C13—O13—C12−171.2 (3)
C15—C16—C17—C180.8 (4)C11—C12—O13—C13−173.3 (2)
N4—C16—C17—C18−176.9 (2)C14—C15—O16—C19−1.6 (4)
C16—C17—C18—C130.4 (4)C16—C15—O16—C19178.7 (2)
C16—C17—C18—N3178.6 (2)C20—C19—O16—C15178.0 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O11i0.821.892.698 (3)168
O4—H5···O21ii0.821.742.562 (3)174
O12—H12···O1iii0.821.922.730 (3)168
O14—H15···O18iv0.822.202.921 (3)147
O14—H15···O17iv0.822.373.055 (3)141
O21—H21···O150.852.192.947 (4)148
O21—H21···O100.852.663.084 (4)113
O21—H22···O50.851.972.798 (4)165
Symmetry codes: (i) −x+5/2, y−1/2, −z+1/2; (ii) −x, −y, −z+1; (iii) −x+5/2, y+1/2, −z+1/2; (iv) x−3/2, −y+1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O11i0.821.892.698 (3)168
O4—H5···O21ii0.821.742.562 (3)174
O12—H12···O1iii0.821.922.730 (3)168
O14—H15···O18iv0.822.202.921 (3)147
O14—H15···O17iv0.822.373.055 (3)141
O21—H21···O150.852.192.947 (4)148
O21—H21···O100.852.663.084 (4)113
O21—H22···O50.851.972.798 (4)165
Symmetry codes: (i) −x+5/2, y−1/2, −z+1/2; (ii) −x, −y, −z+1; (iii) −x+5/2, y+1/2, −z+1/2; (iv) x−3/2, −y+1/2, z−1/2.
Acknowledgements top

The authors thank Heilongjiang University for supporting this study.

references
References top

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