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Acta Cryst. (2009). E65, m200    [ doi:10.1107/S1600536809001500 ]

Bis{6,6'-dimethoxy-2,2'-[ethane-1,2-diylbis(iminomethylene)]diphenolato(1.5-)-[kappa]4O,N,N',O'}praeseodymium(III)

H.-T. Xia, Y.-F. Liu, S.-P. Yang and D.-Q. Wang

Abstract top

The title compound, [Pr(C18H22.5N2O4)2], is isotypic with its Er and Tb analogues. All interatomic distances, angles and the hydrogen bond geometry are very similar for the three structures..

Comment top

Diamine derivatives are potentially multidentate ligands. we have recently reported the crystal structure (C18H24O2N4) (II) (Xia et al., 2006) which is the ligand of the title compound and two complexes [Ce(C18H22N2O4)2] (III) (Liu et al., 2007), [Er(C18H22.5N2O4)2] (IV) (Xia et al., 2009). We report here the crystal structure of new rare earth complex , (I).

In the title complex (I), the coordination environment of the Pr atom and coordination modes of (I) ligands to PrIII ion is in agreement with the complexes reported above (Fig. 1). The average bond lengths of between the Praeseodymium center oxygen atoms are 2.202 (4)Å and nitrogen atom are 2.621 (5) Å, longer than the 2.199 (4)Å and shorter than the 2.624 (4)Å of complexes (III), respectively, shorter than the 2.203 (6)Å and longter than the 2.612 (8)Å of complexes (IV), respectively. The dihedral angles between phenyl ring (C4—C9 ring) and antother phenyl ring are 42.03 (16)°(C12—C17 ring), 47.60 (15)°(C4A—C9A ring) and 15.08 (24)°(C12A—C17A ring) [symmetry codes: (A) 1 - x, 1 - y, z].

In (I), the Pr atom is eight-coordinated by four O atoms and four N atoms from two 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol. The molecules are connected by van der Waals forces, resulting in a three-dimensional network.

Related literature top

For related structures, see: Liu et al. (2007); Xia et al. (2006). For isotypic structures, see: Xia et al. (2009a,b).

Experimental top

A solution of 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene) diphenol (0.328 g, 2 mmol) in ethanol (20 ml), and then a solution of Pr(NO3)3.6H2O (0.435 g, 1 mmol) in ethanol (10 ml) was added. The reaction mixture was stirred for 3 h in the air and then filtered. X-ray quality crystals of (I) were obtained by evaporation of an ethanol solution.

Refinement top

All H atoms were located in difference Fourier maps. H atoms bonded to C, O and N atoms were treated as riding atoms, with C—H distances of 0.93 Å (aryl), 0.96 Å (methyl), 0.97Å (methylene) and N—H distances of 0.90 Å (amino), Uiso(H) = 1.2Ueq(aryl, methylene, NH) or 1.5Ueq(C) (methyl or OH). The H3C bonded to O3 is disordered and were refined with the occupancies ties to 0.5.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are at the 30% probability level. For clarity, H atoms have been omitted. [Symmetry codes: (A) 1 - x, 1 - y, z].
Bis{6,6'-dimethoxy-2,2'-[ethane-1,2-diylbis(iminomethylene)]diphenolato(1.5-)- κ4O,N,N',O'}praeseodymium(III) top
Crystal data top
[Pr(C18H22.5N2O4)2]F(000) = 1648
Mr = 802.67Dx = 1.534 Mg m−3
Orthorhombic, Iba2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2cCell parameters from 4426 reflections
a = 21.977 (3) Åθ = 2.9–28.2°
b = 11.1616 (12) ŵ = 1.46 mm−1
c = 14.1699 (18) ÅT = 298 K
V = 3475.8 (7) Å3Block, brown
Z = 40.22 × 0.13 × 0.08 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer		2878 independent reflections
Radiation source: fine-focus sealed tube2230 reflections with I > 2σ(I)
graphiteRint = 0.030
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −26→24
Tmin = 0.740, Tmax = 0.892k = −10→13
8635 measured reflectionsl = −15→16
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0246P)2 + 7.4954P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2878 reflectionsΔρmax = 0.69 e Å−3
222 parametersΔρmin = −0.37 e Å−3
1 restraintAbsolute structure: Flack (1983), 1271 Freidel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.00 (3)
Crystal data top
[Pr(C18H22.5N2O4)2]V = 3475.8 (7) Å3
Mr = 802.67Z = 4
Orthorhombic, Iba2Mo Kα radiation
a = 21.977 (3) ŵ = 1.46 mm−1
b = 11.1616 (12) ÅT = 298 K
c = 14.1699 (18) Å0.22 × 0.13 × 0.08 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer		2878 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2230 reflections with I > 2σ(I)
Tmin = 0.740, Tmax = 0.892Rint = 0.030
8635 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.070Δρmax = 0.69 e Å−3
S = 1.07Δρmin = −0.37 e Å−3
2878 reflectionsAbsolute structure: Flack (1983), 1271 Freidel pairs
222 parametersFlack parameter: 0.00 (3)
1 restraint
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*/UeqOcc. (<1)
Pr10.50000.50000.34632 (9)0.03225 (10)
N10.6052 (2)0.5730 (5)0.4112 (4)0.0494 (13)
H10.63340.53390.37570.059*
N20.5336 (2)0.7094 (4)0.2803 (3)0.0446 (12)
H20.51540.76410.31860.054*
O10.53496 (16)0.3653 (4)0.4463 (3)0.0437 (9)
O20.5617 (2)0.1320 (4)0.4296 (4)0.0719 (14)
O30.43210 (16)0.5583 (3)0.2419 (3)0.0395 (8)
H3C0.40170.51320.25240.059*0.50
O40.31350 (17)0.5867 (4)0.2690 (3)0.0547 (11)
C10.6158 (3)0.7002 (7)0.3927 (7)0.063 (2)
H1A0.65830.71910.40370.075*
H1B0.59140.74810.43540.075*
C20.5994 (3)0.7299 (6)0.2921 (6)0.061 (2)
H2A0.60910.81290.27850.074*
H2B0.62210.67940.24900.074*
C30.6177 (3)0.5354 (7)0.5091 (5)0.062 (2)
H3A0.58230.55130.54820.074*
H3B0.65160.58090.53420.074*
C40.6322 (3)0.4054 (7)0.5115 (4)0.0574 (19)
C50.5892 (3)0.3256 (7)0.4762 (5)0.048 (2)
C60.6047 (3)0.2033 (7)0.4686 (5)0.0616 (19)
C70.6621 (3)0.1636 (9)0.5003 (6)0.071 (3)
H70.67250.08300.49680.085*
C80.7014 (4)0.2440 (10)0.5356 (6)0.082 (3)
H80.73940.21740.55540.098*
C90.6885 (3)0.3609 (9)0.5435 (5)0.073 (2)
H90.71680.41280.57010.088*
C100.5795 (4)0.0130 (7)0.4047 (8)0.105 (3)
H10A0.61620.01590.36800.157*
H10B0.5478−0.02390.36820.157*
H10C0.5864−0.03280.46100.157*
C110.5117 (3)0.7376 (6)0.1847 (5)0.0556 (17)
H11A0.52130.67210.14220.067*
H11B0.53160.80930.16160.067*
C120.4433 (3)0.7570 (6)0.1875 (4)0.0491 (15)
C130.4073 (3)0.6640 (6)0.2217 (5)0.0414 (17)
C140.3448 (3)0.6836 (6)0.2338 (4)0.0456 (14)
C150.3194 (3)0.7933 (7)0.2106 (5)0.0562 (18)
H150.27790.80670.21830.067*
C160.3569 (4)0.8827 (7)0.1757 (6)0.068 (2)
H160.33990.95640.16000.082*
C170.4164 (4)0.8664 (6)0.1639 (5)0.066 (2)
H170.44030.92810.13990.079*
C180.2529 (3)0.6065 (8)0.2982 (6)0.079 (2)
H18A0.25090.67850.33510.119*
H18B0.23930.54000.33560.119*
H18C0.22720.61450.24380.119*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pr10.02417 (14)0.03686 (17)0.03572 (16)−0.00020 (19)0.0000.000
N10.030 (2)0.060 (3)0.058 (3)0.001 (2)−0.002 (2)−0.025 (3)
N20.036 (3)0.043 (3)0.055 (3)−0.009 (2)0.014 (2)−0.004 (2)
O10.031 (2)0.059 (3)0.040 (2)0.0115 (19)−0.0036 (17)0.005 (2)
O20.067 (3)0.057 (3)0.092 (4)0.020 (3)0.017 (3)0.023 (3)
O30.041 (2)0.037 (2)0.041 (2)0.0023 (19)−0.0060 (19)0.0011 (18)
O40.035 (2)0.065 (3)0.064 (3)0.005 (2)−0.0034 (19)0.002 (2)
C10.033 (4)0.068 (5)0.088 (5)−0.013 (3)0.006 (4)−0.031 (4)
C20.045 (4)0.050 (4)0.090 (6)−0.016 (3)0.020 (4)−0.011 (4)
C30.044 (4)0.090 (6)0.052 (4)0.001 (3)−0.008 (3)−0.025 (4)
C40.043 (3)0.090 (6)0.040 (4)0.020 (4)−0.003 (3)−0.009 (4)
C50.042 (4)0.069 (6)0.031 (4)0.017 (4)0.006 (3)0.010 (4)
C60.054 (4)0.082 (5)0.049 (4)0.023 (4)0.008 (3)0.018 (4)
C70.054 (5)0.091 (7)0.067 (6)0.030 (5)0.013 (4)0.025 (5)
C80.062 (5)0.116 (8)0.067 (5)0.032 (5)−0.008 (4)0.013 (5)
C90.051 (4)0.116 (7)0.054 (4)0.016 (5)−0.011 (3)−0.008 (5)
C100.100 (6)0.066 (5)0.149 (8)0.021 (5)0.023 (6)0.020 (6)
C110.064 (5)0.044 (3)0.058 (4)−0.006 (3)0.022 (3)0.002 (3)
C120.059 (4)0.043 (4)0.045 (3)0.010 (3)0.006 (3)0.004 (3)
C130.045 (4)0.046 (4)0.033 (4)0.006 (4)−0.004 (3)−0.004 (3)
C140.051 (3)0.049 (4)0.037 (3)0.009 (3)−0.005 (3)−0.003 (3)
C150.053 (4)0.057 (4)0.058 (5)0.016 (4)−0.008 (3)−0.007 (3)
C160.078 (6)0.051 (5)0.074 (5)0.019 (4)−0.001 (4)0.010 (4)
C170.079 (5)0.049 (4)0.071 (5)0.005 (4)0.012 (4)0.012 (4)
C180.044 (4)0.099 (6)0.095 (5)−0.001 (4)0.001 (4)0.008 (5)
Geometric parameters (Å, °) top
Pr1—O32.200 (4)C3—H3B0.9700
Pr1—O3i2.200 (4)C4—C51.392 (10)
Pr1—O1i2.204 (4)C4—C91.409 (9)
Pr1—O12.204 (4)C5—C61.411 (10)
Pr1—N1i2.619 (4)C6—C71.411 (9)
Pr1—N12.619 (4)C7—C81.344 (12)
Pr1—N2i2.623 (5)C7—H70.9300
Pr1—N22.623 (5)C8—C91.340 (12)
Pr1—H3C2.5421C8—H80.9300
N1—C11.462 (9)C9—H90.9300
N1—C31.475 (8)C10—H10A0.9600
N1—H10.9100C10—H10B0.9600
N2—C111.471 (8)C10—H10C0.9600
N2—C21.472 (8)C11—C121.519 (9)
N2—H20.9100C11—H11A0.9700
O1—C51.340 (7)C11—H11B0.9700
O2—C61.353 (8)C12—C131.392 (9)
O2—C101.428 (9)C12—C171.397 (9)
O3—C131.330 (7)C13—C141.402 (8)
O3—H3C0.8500C14—C151.386 (9)
O4—C141.375 (7)C15—C161.386 (11)
O4—C181.413 (8)C15—H150.9300
C1—C21.508 (9)C16—C171.332 (10)
C1—H1A0.9700C16—H160.9300
C1—H1B0.9700C17—H170.9300
C2—H2A0.9700C18—H18A0.9600
C2—H2B0.9700C18—H18B0.9600
C3—C41.486 (11)C18—H18C0.9600
C3—H3A0.9700
O3—Pr1—O3i95.47 (19)N2—C2—H2B110.1
O3—Pr1—O1i89.65 (13)C1—C2—H2B110.1
O3i—Pr1—O1i150.52 (13)H2A—C2—H2B108.4
O3—Pr1—O1150.52 (13)N1—C3—C4109.8 (5)
O3i—Pr1—O189.65 (13)N1—C3—H3A109.7
O1i—Pr1—O1100.0 (2)C4—C3—H3A109.7
O3—Pr1—N1i74.28 (15)N1—C3—H3B109.7
O3i—Pr1—N1i137.99 (15)C4—C3—H3B109.7
O1i—Pr1—N1i71.27 (16)H3A—C3—H3B108.2
O1—Pr1—N1i82.53 (15)C5—C4—C9119.1 (7)
O3—Pr1—N1137.99 (15)C5—C4—C3118.1 (5)
O3i—Pr1—N174.28 (15)C9—C4—C3122.7 (7)
O1i—Pr1—N182.53 (15)O1—C5—C4120.4 (6)
O1—Pr1—N171.27 (16)O1—C5—C6120.6 (7)
N1i—Pr1—N1138.9 (2)C4—C5—C6118.9 (6)
O3—Pr1—N2i80.36 (14)O2—C6—C7124.7 (7)
O3i—Pr1—N2i71.79 (14)O2—C6—C5115.6 (6)
O1i—Pr1—N2i137.63 (14)C7—C6—C5119.6 (8)
O1—Pr1—N2i73.73 (16)C8—C7—C6119.0 (9)
N1i—Pr1—N2i66.38 (16)C8—C7—H7120.5
N1—Pr1—N2i130.63 (15)C6—C7—H7120.5
O3—Pr1—N271.79 (14)C9—C8—C7123.0 (8)
O3i—Pr1—N280.36 (14)C9—C8—H8118.5
O1i—Pr1—N273.73 (16)C7—C8—H8118.5
O1—Pr1—N2137.63 (14)C8—C9—C4120.2 (8)
N1i—Pr1—N2130.63 (15)C8—C9—H9119.9
N1—Pr1—N266.38 (16)C4—C9—H9119.9
N2i—Pr1—N2138.2 (2)O2—C10—H10A109.5
O3—Pr1—H3C18.9O2—C10—H10B109.5
O3i—Pr1—H3C104.0H10A—C10—H10B109.5
O1i—Pr1—H3C90.0O2—C10—H10C109.5
O1—Pr1—H3C132.2H10A—C10—H10C109.5
N1i—Pr1—H3C56.7H10B—C10—H10C109.5
N1—Pr1—H3C156.4N2—C11—C12109.3 (5)
N2i—Pr1—H3C68.0N2—C11—H11A109.8
N2—Pr1—H3C90.0C12—C11—H11A109.8
C1—N1—C3114.5 (6)N2—C11—H11B109.8
C1—N1—Pr1112.3 (4)C12—C11—H11B109.8
C3—N1—Pr1113.9 (4)H11A—C11—H11B108.3
C1—N1—H1105.0C13—C12—C17119.7 (6)
C3—N1—H1105.0C13—C12—C11117.7 (5)
Pr1—N1—H1105.0C17—C12—C11122.4 (6)
C11—N2—C2113.1 (5)O3—C13—C12120.2 (6)
C11—N2—Pr1115.2 (4)O3—C13—C14120.9 (6)
C2—N2—Pr1112.0 (4)C12—C13—C14118.9 (6)
C11—N2—H2105.1O4—C14—C15125.4 (6)
C2—N2—H2105.1O4—C14—C13114.3 (5)
Pr1—N2—H2105.1C15—C14—C13120.2 (6)
C5—O1—Pr1137.6 (4)C16—C15—C14118.8 (7)
C6—O2—C10117.1 (6)C16—C15—H15120.6
C13—O3—Pr1133.2 (4)C14—C15—H15120.6
C13—O3—H3C103.9C17—C16—C15122.0 (7)
Pr1—O3—H3C103.9C17—C16—H16119.0
C14—O4—C18117.0 (5)C15—C16—H16119.0
N1—C1—C2110.2 (6)C16—C17—C12120.3 (7)
N1—C1—H1A109.6C16—C17—H17119.8
C2—C1—H1A109.6C12—C17—H17119.8
N1—C1—H1B109.6O4—C18—H18A109.5
C2—C1—H1B109.6O4—C18—H18B109.5
H1A—C1—H1B108.1H18A—C18—H18B109.5
N2—C2—C1108.0 (6)O4—C18—H18C109.5
N2—C2—H2A110.1H18A—C18—H18C109.5
C1—C2—H2A110.1H18B—C18—H18C109.5
O3—Pr1—N1—C119.9 (5)N1—C1—C2—N263.9 (7)
O3i—Pr1—N1—C1100.5 (5)C1—N1—C3—C4−155.2 (5)
O1i—Pr1—N1—C1−61.2 (4)Pr1—N1—C3—C473.6 (5)
O1—Pr1—N1—C1−164.4 (5)N1—C3—C4—C5−57.9 (8)
N1i—Pr1—N1—C1−111.1 (5)N1—C3—C4—C9118.9 (6)
N2i—Pr1—N1—C1148.5 (4)Pr1—O1—C5—C453.9 (9)
N2—Pr1—N1—C114.3 (4)Pr1—O1—C5—C6−123.3 (6)
O3—Pr1—N1—C3152.2 (4)C9—C4—C5—O1179.2 (6)
O3i—Pr1—N1—C3−127.3 (4)C3—C4—C5—O1−3.9 (9)
O1i—Pr1—N1—C371.1 (4)C9—C4—C5—C6−3.5 (10)
O1—Pr1—N1—C3−32.2 (4)C3—C4—C5—C6173.4 (6)
N1i—Pr1—N1—C321.1 (4)C10—O2—C6—C7−10.9 (10)
N2i—Pr1—N1—C3−79.3 (4)C10—O2—C6—C5168.7 (7)
N2—Pr1—N1—C3146.6 (4)O1—C5—C6—O20.3 (9)
O3—Pr1—N2—C11−26.1 (4)C4—C5—C6—O2−177.0 (6)
O3i—Pr1—N2—C1172.9 (4)O1—C5—C6—C7179.9 (6)
O1i—Pr1—N2—C11−121.3 (4)C4—C5—C6—C72.6 (10)
O1—Pr1—N2—C11151.7 (3)O2—C6—C7—C8178.3 (7)
N1i—Pr1—N2—C11−75.0 (4)C5—C6—C7—C8−1.2 (11)
N1—Pr1—N2—C11149.9 (4)C6—C7—C8—C90.9 (13)
N2i—Pr1—N2—C1124.7 (3)C7—C8—C9—C4−1.9 (13)
O3—Pr1—N2—C2−157.4 (5)C5—C4—C9—C83.2 (11)
O3i—Pr1—N2—C2−58.3 (4)C3—C4—C9—C8−173.5 (7)
O1i—Pr1—N2—C2107.5 (5)C2—N2—C11—C12−160.1 (5)
O1—Pr1—N2—C220.5 (5)Pr1—N2—C11—C1269.3 (5)
N1i—Pr1—N2—C2153.8 (4)N2—C11—C12—C13−57.6 (7)
N1—Pr1—N2—C218.7 (4)N2—C11—C12—C17117.5 (7)
N2i—Pr1—N2—C2−106.6 (4)Pr1—O3—C13—C1264.1 (8)
O3—Pr1—O1—C5144.6 (6)Pr1—O3—C13—C14−116.3 (6)
O3i—Pr1—O1—C544.1 (6)C17—C12—C13—O3178.1 (6)
O1i—Pr1—O1—C5−107.9 (6)C11—C12—C13—O3−6.7 (9)
N1i—Pr1—O1—C5−177.3 (6)C17—C12—C13—C14−1.5 (10)
N1—Pr1—O1—C5−29.4 (6)C11—C12—C13—C14173.8 (5)
N2i—Pr1—O1—C5115.2 (6)C18—O4—C14—C15−11.0 (9)
N2—Pr1—O1—C5−31.1 (7)C18—O4—C14—C13169.3 (6)
O3i—Pr1—O3—C13−117.1 (6)O3—C13—C14—O41.1 (9)
O1i—Pr1—O3—C1333.8 (5)C12—C13—C14—O4−179.3 (5)
O1—Pr1—O3—C13143.9 (5)O3—C13—C14—C15−178.6 (6)
N1i—Pr1—O3—C13104.4 (6)C12—C13—C14—C150.9 (10)
N1—Pr1—O3—C13−44.6 (6)O4—C14—C15—C16−179.9 (6)
N2i—Pr1—O3—C13172.5 (6)C13—C14—C15—C16−0.2 (11)
N2—Pr1—O3—C13−39.1 (5)C14—C15—C16—C170.0 (12)
C3—N1—C1—C2−177.7 (5)C15—C16—C17—C12−0.5 (12)
Pr1—N1—C1—C2−45.7 (6)C13—C12—C17—C161.2 (11)
C11—N2—C2—C1178.9 (6)C11—C12—C17—C16−173.8 (7)
Pr1—N2—C2—C1−48.8 (6)
Symmetry codes: (i) −x+1, −y+1, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3C···O40.852.122.653 (5)121
N1—H1···O4i0.912.343.229 (6)167
N2—H2···O2i0.912.593.464 (6)162
Symmetry codes: (i) −x+1, −y+1, z.
Table 1
Selected geometric parameters (Å) top
Pr1—O32.200 (4)Pr1—N1i2.619 (4)
Pr1—O3i2.200 (4)Pr1—N12.619 (4)
Pr1—O1i2.204 (4)Pr1—N2i2.623 (5)
Pr1—O12.204 (4)Pr1—N22.623 (5)
Symmetry codes: (i) −x+1, −y+1, z.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3C···O40.852.122.653 (5)121
N1—H1···O4i0.912.343.229 (6)167
N2—H2···O2i0.912.593.464 (6)162
Symmetry codes: (i) −x+1, −y+1, z.
Acknowledgements top

We acknowledge the financial support of the Huaihai Institute of Technology Science Foundation.

references
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