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Acta Cryst. (2007). E63, m2929    [ doi:10.1107/S1600536807054931 ]

{Bis[2-(3,4-methylenedioxybenzylamino)ethyl]amine}dichloridozinc(II) hemihydrate

L.-J. Han, S.-P. Yang, D.-Q. Wang and H.-T. Xia

Abstract top

In the title compound, [ZnCl2(C20H25N3O4)]·0.5H2O, the ZnII ion assumes a trigonal bipyramidal coordination geometry formed by a tridentate amine ligand and two Cl- anions. The tridentate amine ligand chelates the ZnII ion in a meridional configuration. The extensive hydrogen-bonding network helps to stabilize the crystal structure.

Comment top

We have reported recently the crystyl structure of a ZnII complex (Han et al., 2006). As part of our study of the ZnII complexes with the diamine derives, we report here the crystal structure of a new ZnII complex.

The title complex is a mononuclear compound, and the central zinc ion is five-coordinated by two Cl− ions and three N atoms from a tridentate ligand N,N'-bis[(3,4-methylenedioxybenzyl)-2,2'-diaminodiethyl]amine (Fig. 1). The tridentate ligand chelates to the ZnII ion in a meridional configuration. The coordination geometry around the ZnII ion is a distorted trigonal bipyramid. The Zn—Cl and Zn—N bond lengths (Table 1) are slightly longer than those found in the related ZnII complex (Han et al., 2006).

The extensive hydrogen bonding network helps to stabilize the crystal structure (Table. 2).

Related literature top

For related literature, see: Han et al. (2006).

Experimental top

The ethanol solution (20 ml) of N,N'-bis[(3,4-methylenedioxybenzyl)-2,2'-diaminodiethyl]amine (1.86 g, 5 mmol) was mixed with the ethanol solution (30 ml) of zinc chloride (1.36 g, 10 mmol), the mixture was stirred for 4 h at 340 K. The crude solid obtained was filtered off and washed successively with ethanol. Single crystals of the title compound were obtained by slow evaporation of a DMF-chloroform-ethanol (1:5:10) solution of the crude product over a period of three weeks.

Refinement top

H atoms were placed in calculated positions with C—H = 0.93 (aromatic), 0.97 (methylene), N—H = 0.91 and O—H = 0.82 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(carrier). Site occupancy factor for O5 atom was refined and converged to 0.529 (3), in the final cycles of refinement it was fixed as 0.5. The crystal quality is poor, the accuracy of the structure determination is low. The highest peak in difference Fourier map is 2.1 Å apart from C18 atom.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecule of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
{Bis[2-(3,4-methylenedioxybenzylamino)ethyl]amine}dichloridozinc(II) hemihydrate top
Crystal data top
[ZnCl2(C20H25N3O4)]·0.5H2OF000 = 1068
Mr = 516.71Dx = 1.514 Mg m−3
Monoclinic, P21/cMelting point: 504-506 K
Hall symbol: -P 2ybcMo Kα radiation
λ = 0.71073 Å
a = 24.042 (3) ÅCell parameters from 2613 reflections
b = 13.0193 (18) Åθ = 3.0–22.0º
c = 7.2678 (14) ŵ = 1.35 mm−1
β = 94.934 (2)ºT = 298 (2) K
V = 2266.5 (6) Å3Prism, colorless
Z = 40.57 × 0.15 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		4003 independent reflections
Radiation source: fine-focus sealed tube2735 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.077
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −27→28
Tmin = 0.513, Tmax = 0.855k = −11→15
11175 measured reflectionsl = −8→8
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)] = 0.104H-atom parameters constrained
wR(F2) = 0.277  w = 1/[σ2(Fo2) + (0.0881P)2 + 21.9915P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
4003 reflectionsΔρmax = 1.46 e Å−3
280 parametersΔρmin = −0.58 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[ZnCl2(C20H25N3O4)]·0.5H2OV = 2266.5 (6) Å3
Mr = 516.71Z = 4
Monoclinic, P21/cMo Kα
a = 24.042 (3) ŵ = 1.35 mm−1
b = 13.0193 (18) ÅT = 298 (2) K
c = 7.2678 (14) Å0.57 × 0.15 × 0.12 mm
β = 94.934 (2)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		4003 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2735 reflections with I > 2σ(I)
Tmin = 0.513, Tmax = 0.855Rint = 0.077
11175 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.104H-atom parameters constrained
wR(F2) = 0.277  w = 1/[σ2(Fo2) + (0.0881P)2 + 21.9915P]
where P = (Fo2 + 2Fc2)/3
S = 1.12Δρmax = 1.46 e Å−3
4003 reflectionsΔρmin = −0.58 e Å−3
280 parameters
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 > 2sigma(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)
Zn10.25115 (5)0.52956 (9)0.26489 (17)0.0442 (4)
Cl10.22268 (12)0.6661 (2)0.0855 (4)0.0546 (7)
Cl20.28847 (14)0.3967 (3)0.0916 (6)0.0838 (11)
N10.3374 (3)0.5641 (7)0.3637 (12)0.049 (2)
H10.35450.50300.39200.058*
N20.1760 (4)0.4473 (7)0.3044 (12)0.049 (2)
H20.18630.38210.33740.059*
N30.2405 (3)0.5717 (7)0.5416 (12)0.048 (2)
H30.22780.63760.53800.058*
O10.5505 (3)0.7611 (6)0.4817 (13)0.068 (2)
O20.6010 (3)0.6208 (7)0.4070 (13)0.067 (2)
O3−0.0658 (4)0.3908 (7)0.2274 (16)0.086 (3)
O4−0.0591 (3)0.2137 (7)0.2272 (13)0.071 (2)
O50.2238 (8)0.2319 (15)0.295 (4)0.118 (10)0.50
H5A0.24400.27560.24490.141*0.50
H5B0.24430.19890.37600.141*0.50
C10.3688 (5)0.6133 (10)0.2204 (16)0.062 (3)
H1A0.35670.68420.20520.074*
H1B0.36000.57840.10370.074*
C20.4317 (5)0.6111 (10)0.2678 (16)0.057 (3)
C30.4591 (5)0.6960 (8)0.3597 (16)0.055 (3)
H3A0.43950.75410.39120.067*
C40.5154 (4)0.6885 (8)0.3996 (16)0.050 (3)
C50.5446 (4)0.6027 (9)0.3560 (15)0.050 (3)
C60.5194 (5)0.5227 (9)0.2668 (16)0.055 (3)
H60.53970.46540.23580.066*
C70.4631 (5)0.5277 (9)0.2231 (17)0.060 (3)
H70.44540.47280.16080.073*
C80.6019 (5)0.7118 (11)0.521 (2)0.076 (4)
H8A0.60710.69340.65040.091*
H8B0.63220.75680.49250.091*
C90.1359 (5)0.4388 (9)0.1357 (16)0.058 (3)
H9A0.15540.40920.03690.070*
H9B0.12420.50740.09750.070*
C100.0845 (5)0.3750 (9)0.1598 (16)0.054 (3)
C110.0345 (5)0.4233 (9)0.1839 (17)0.060 (3)
H110.03170.49450.18580.072*
C12−0.0115 (4)0.3608 (9)0.2050 (16)0.056 (3)
C13−0.0067 (4)0.2563 (9)0.2025 (17)0.055 (3)
C140.0417 (5)0.2097 (9)0.1823 (17)0.057 (3)
H140.04410.13840.18120.068*
C150.0885 (5)0.2694 (10)0.1631 (17)0.059 (3)
H150.12280.23800.15240.071*
C16−0.0944 (5)0.2985 (10)0.252 (2)0.069 (3)
H16A−0.12700.29480.16420.083*
H16B−0.10690.29660.37560.083*
C170.3368 (5)0.6222 (10)0.5386 (17)0.060 (3)
H17A0.37360.62130.60490.072*
H17B0.32640.69310.51300.072*
C180.2957 (5)0.5732 (11)0.6514 (17)0.066 (3)
H18A0.30730.50370.68360.079*
H18B0.29300.61160.76470.079*
C190.1509 (5)0.4926 (10)0.4628 (17)0.061 (3)
H19A0.12270.44690.50450.073*
H19B0.13330.55750.42760.073*
C200.1968 (5)0.5093 (10)0.6158 (16)0.060 (3)
H20A0.18210.54430.71890.072*
H20B0.21210.44380.65910.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0434 (6)0.0455 (7)0.0439 (7)0.0000 (6)0.0041 (5)0.0023 (6)
Cl10.0561 (16)0.0485 (15)0.0583 (18)0.0004 (12)0.0004 (13)0.0091 (13)
Cl20.070 (2)0.071 (2)0.112 (3)0.0116 (17)0.0176 (19)−0.034 (2)
N10.045 (5)0.045 (5)0.056 (6)−0.003 (4)0.008 (4)0.004 (4)
N20.048 (5)0.044 (5)0.056 (6)−0.003 (4)0.011 (4)−0.003 (4)
N30.030 (4)0.065 (6)0.048 (5)−0.005 (4)−0.007 (4)0.017 (4)
O10.056 (5)0.056 (5)0.095 (7)−0.012 (4)0.015 (5)−0.008 (5)
O20.054 (5)0.067 (5)0.081 (6)−0.002 (4)0.003 (4)0.005 (5)
O30.056 (5)0.068 (6)0.135 (9)0.003 (5)0.017 (5)−0.004 (6)
O40.049 (5)0.069 (6)0.095 (7)−0.016 (4)0.009 (4)−0.006 (5)
O50.061 (12)0.068 (12)0.22 (3)−0.001 (10)−0.028 (15)0.059 (16)
C10.067 (7)0.075 (8)0.044 (7)−0.005 (6)0.010 (6)0.021 (6)
C20.052 (6)0.063 (7)0.055 (7)−0.006 (6)0.004 (5)0.013 (6)
C30.066 (7)0.039 (6)0.061 (8)0.002 (5)0.002 (6)0.000 (5)
C40.050 (6)0.044 (6)0.057 (7)−0.011 (5)0.003 (5)0.009 (5)
C50.040 (6)0.056 (7)0.055 (7)−0.001 (5)0.012 (5)0.009 (6)
C60.063 (7)0.049 (7)0.055 (7)0.003 (6)0.009 (6)0.002 (6)
C70.064 (8)0.060 (8)0.058 (7)−0.018 (6)0.006 (6)0.004 (6)
C80.056 (8)0.077 (9)0.092 (11)−0.018 (7)−0.004 (7)0.004 (8)
C90.067 (7)0.062 (7)0.047 (7)−0.006 (6)0.012 (6)0.004 (6)
C100.058 (7)0.052 (7)0.051 (7)−0.011 (6)0.000 (5)0.004 (5)
C110.069 (8)0.039 (6)0.072 (8)−0.009 (6)−0.002 (6)0.001 (6)
C120.047 (6)0.059 (7)0.060 (8)0.000 (5)0.002 (5)0.004 (6)
C130.045 (6)0.055 (7)0.063 (8)−0.009 (5)−0.007 (5)−0.007 (6)
C140.060 (7)0.047 (6)0.063 (8)0.003 (6)0.001 (6)−0.003 (6)
C150.050 (6)0.065 (8)0.060 (8)0.000 (6)−0.002 (5)−0.007 (6)
C160.052 (7)0.078 (9)0.077 (9)−0.003 (7)0.001 (6)−0.007 (7)
C170.048 (6)0.063 (7)0.069 (8)−0.002 (6)0.002 (6)−0.010 (6)
C180.055 (7)0.089 (9)0.051 (7)−0.003 (7)−0.011 (6)−0.006 (7)
C190.049 (6)0.073 (8)0.063 (8)−0.002 (6)0.016 (6)−0.001 (6)
C200.059 (7)0.069 (8)0.055 (7)0.001 (6)0.025 (6)−0.002 (6)
Geometric parameters (Å, °) top
Zn1—Cl12.275 (3)C4—C51.371 (15)
Zn1—Cl22.361 (3)C5—C61.344 (15)
Zn1—N12.183 (8)C6—C71.363 (16)
Zn1—N22.141 (8)C6—H60.9300
Zn1—N32.121 (9)C7—H70.9300
N1—C11.483 (13)C8—H8A0.9700
N1—C171.481 (14)C8—H8B0.9700
N1—H10.9100C9—C101.512 (15)
N2—C191.468 (14)C9—H9A0.9700
N2—C91.497 (14)C9—H9B0.9700
N2—H20.9100C10—C111.381 (16)
N3—C201.467 (13)C10—C151.379 (16)
N3—C181.487 (13)C11—C121.392 (16)
N3—H30.9100C11—H110.9300
O1—C41.369 (13)C12—C131.366 (16)
O1—C81.400 (15)C13—C141.332 (16)
O2—C51.395 (13)C14—C151.384 (16)
O2—C81.444 (16)C14—H140.9300
O3—C121.385 (13)C15—H150.9300
O3—C161.404 (15)C16—H16A0.9700
O4—C131.402 (13)C16—H16B0.9700
O4—C161.415 (15)C17—C181.482 (17)
O5—H5A0.8505C17—H17A0.9700
O5—H5B0.8504C17—H17B0.9700
C1—C21.521 (16)C18—H18A0.9700
C1—H1A0.9700C18—H18B0.9700
C1—H1B0.9700C19—C201.514 (16)
C2—C71.378 (17)C19—H19A0.9700
C2—C31.425 (16)C19—H19B0.9700
C3—C41.363 (15)C20—H20A0.9700
C3—H3A0.9300C20—H20B0.9700
N3—Zn1—N280.2 (3)O2—C8—H8A110.3
N3—Zn1—N179.8 (3)O1—C8—H8B110.3
N2—Zn1—N1148.0 (3)O2—C8—H8B110.3
N3—Zn1—Cl1106.6 (3)H8A—C8—H8B108.6
N2—Zn1—Cl1104.6 (3)N2—C9—C10114.9 (9)
N1—Zn1—Cl1104.9 (2)N2—C9—H9A108.5
N3—Zn1—Cl2141.0 (3)C10—C9—H9A108.5
N2—Zn1—Cl293.9 (3)N2—C9—H9B108.5
N1—Zn1—Cl286.1 (3)C10—C9—H9B108.5
Cl1—Zn1—Cl2112.09 (14)H9A—C9—H9B107.5
C1—N1—C17115.2 (9)C11—C10—C15120.8 (11)
C1—N1—Zn1112.6 (7)C11—C10—C9119.6 (10)
C17—N1—Zn1107.9 (6)C15—C10—C9119.6 (11)
C1—N1—H1106.9C10—C11—C12117.1 (10)
C17—N1—H1106.9C10—C11—H11121.4
Zn1—N1—H1106.9C12—C11—H11121.4
C19—N2—C9113.1 (9)C13—C12—O3111.3 (10)
C19—N2—Zn1108.2 (7)C13—C12—C11120.8 (11)
C9—N2—Zn1114.7 (7)O3—C12—C11127.8 (11)
C19—N2—H2106.8C14—C13—C12122.1 (11)
C9—N2—H2106.8C14—C13—O4129.6 (11)
Zn1—N2—H2106.8C12—C13—O4108.3 (10)
C20—N3—C18116.3 (9)C13—C14—C15118.7 (11)
C20—N3—Zn1110.7 (7)C13—C14—H14120.6
C18—N3—Zn1109.8 (7)C15—C14—H14120.6
C20—N3—H3106.5C10—C15—C14120.4 (11)
C18—N3—H3106.5C10—C15—H15119.8
Zn1—N3—H3106.5C14—C15—H15119.8
C4—O1—C8105.8 (9)O3—C16—O4110.1 (9)
C5—O2—C8104.9 (9)O3—C16—H16A109.6
C12—O3—C16104.6 (9)O4—C16—H16A109.6
C13—O4—C16105.3 (9)O3—C16—H16B109.6
H5A—O5—H5B108.5O4—C16—H16B109.6
N1—C1—C2112.8 (9)H16A—C16—H16B108.1
N1—C1—H1A109.0C18—C17—N1108.2 (10)
C2—C1—H1A109.0C18—C17—H17A110.1
N1—C1—H1B109.0N1—C17—H17A110.1
C2—C1—H1B109.0C18—C17—H17B110.1
H1A—C1—H1B107.8N1—C17—H17B110.1
C7—C2—C3118.7 (10)H17A—C17—H17B108.4
C7—C2—C1121.2 (11)N3—C18—C17108.3 (10)
C3—C2—C1120.2 (11)N3—C18—H18A110.0
C4—C3—C2117.1 (11)C17—C18—H18A110.0
C4—C3—H3A121.5N3—C18—H18B110.0
C2—C3—H3A121.5C17—C18—H18B110.0
C3—C4—O1127.3 (11)H18A—C18—H18B108.4
C3—C4—C5121.9 (10)N2—C19—C20108.1 (9)
O1—C4—C5110.8 (9)N2—C19—H19A110.1
C6—C5—C4121.6 (10)C20—C19—H19A110.1
C6—C5—O2130.4 (10)N2—C19—H19B110.1
C4—C5—O2107.9 (10)C20—C19—H19B110.1
C5—C6—C7118.2 (11)H19A—C19—H19B108.4
C5—C6—H6120.9N3—C20—C19108.0 (9)
C7—C6—H6120.9N3—C20—H20A110.1
C6—C7—C2122.5 (11)C19—C20—H20A110.1
C6—C7—H7118.8N3—C20—H20B110.1
C2—C7—H7118.8C19—C20—H20B110.1
O1—C8—O2106.9 (10)H20A—C20—H20B108.4
O1—C8—H8A110.3
N3—Zn1—N1—C1−143.6 (8)C4—C5—C6—C7−1.3 (17)
N2—Zn1—N1—C1164.1 (8)O2—C5—C6—C7−175.6 (11)
Cl1—Zn1—N1—C1−39.0 (8)C5—C6—C7—C2−0.3 (18)
Cl2—Zn1—N1—C172.9 (8)C3—C2—C7—C61.3 (18)
N3—Zn1—N1—C17−15.4 (7)C1—C2—C7—C6−178.7 (11)
N2—Zn1—N1—C17−67.7 (10)C4—O1—C8—O218.4 (13)
Cl1—Zn1—N1—C1789.3 (7)C5—O2—C8—O1−19.4 (13)
Cl2—Zn1—N1—C17−158.9 (7)C19—N2—C9—C10−59.0 (13)
N3—Zn1—N2—C1919.0 (7)Zn1—N2—C9—C10176.3 (8)
N1—Zn1—N2—C1971.2 (10)N2—C9—C10—C11101.8 (13)
Cl1—Zn1—N2—C19−85.8 (7)N2—C9—C10—C15−76.2 (14)
Cl2—Zn1—N2—C19160.1 (7)C15—C10—C11—C12−2.1 (18)
N3—Zn1—N2—C9146.3 (8)C9—C10—C11—C12179.9 (10)
N1—Zn1—N2—C9−161.5 (7)C16—O3—C12—C134.1 (14)
Cl1—Zn1—N2—C941.5 (8)C16—O3—C12—C11−176.9 (13)
Cl2—Zn1—N2—C9−72.5 (7)C10—C11—C12—C130.2 (18)
N2—Zn1—N3—C2010.7 (7)C10—C11—C12—O3−178.7 (12)
N1—Zn1—N3—C20−144.1 (8)O3—C12—C13—C14180.0 (11)
Cl1—Zn1—N3—C20113.2 (7)C11—C12—C13—C141(2)
Cl2—Zn1—N3—C20−73.4 (8)O3—C12—C13—O4−1.1 (14)
N2—Zn1—N3—C18140.4 (8)C11—C12—C13—O4179.8 (11)
N1—Zn1—N3—C18−14.4 (8)C16—O4—C13—C14176.4 (13)
Cl1—Zn1—N3—C18−117.1 (7)C16—O4—C13—C12−2.4 (13)
Cl2—Zn1—N3—C1856.2 (9)C12—C13—C14—C15−0.1 (19)
C17—N1—C1—C271.4 (13)O4—C13—C14—C15−178.8 (12)
Zn1—N1—C1—C2−164.2 (8)C11—C10—C15—C143.0 (19)
N1—C1—C2—C786.2 (14)C9—C10—C15—C14−179.1 (11)
N1—C1—C2—C3−93.9 (13)C13—C14—C15—C10−1.8 (18)
C7—C2—C3—C4−0.7 (17)C12—O3—C16—O4−5.6 (14)
C1—C2—C3—C4179.4 (10)C13—O4—C16—O35.0 (14)
C2—C3—C4—O1178.0 (11)C1—N1—C17—C18169.6 (10)
C2—C3—C4—C5−0.8 (17)Zn1—N1—C17—C1842.8 (11)
C8—O1—C4—C3170.4 (12)C20—N3—C18—C17169.0 (10)
C8—O1—C4—C5−10.7 (13)Zn1—N3—C18—C1742.4 (12)
C3—C4—C5—C61.9 (18)N1—C17—C18—N3−57.0 (13)
O1—C4—C5—C6−177.1 (10)C9—N2—C19—C20−173.0 (9)
C3—C4—C5—O2177.4 (10)Zn1—N2—C19—C20−44.8 (11)
O1—C4—C5—O2−1.6 (13)C18—N3—C20—C19−163.9 (10)
C8—O2—C5—C6−172.2 (12)Zn1—N3—C20—C19−37.8 (11)
C8—O2—C5—C412.8 (12)N2—C19—C20—N355.1 (13)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.912.373.216 (12)155
N2—H2···O50.912.193.03 (2)155
N3—H3···Cl1ii0.912.583.459 (9)162
O5—H5A···Cl20.852.253.10 (2)173
O5—H5B···Cl2iii0.852.203.05 (2)173
C8—H8B···Cl2iv0.972.743.713 (14)175
C15—H15···O50.932.563.35 (2)143
C20—H20B···O5iii0.972.503.44 (2)164
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2.
Selected geometric parameters (Å) top
Zn1—Cl12.275 (3)Zn1—N22.141 (8)
Zn1—Cl22.361 (3)Zn1—N32.121 (9)
Zn1—N12.183 (8)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.912.373.216 (12)155
N2—H2···O50.912.193.03 (2)155
N3—H3···Cl1ii0.912.583.459 (9)162
O5—H5A···Cl20.852.253.10 (2)173
O5—H5B···Cl2iii0.852.203.05 (2)173
C8—H8B···Cl2iv0.972.743.713 (14)175
C15—H15···O50.932.563.35 (2)143
C20—H20B···O5iii0.972.503.44 (2)164
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2.
Acknowledgements top

The work is supported by Science Foundation of Huaihai Institute of Technology, China.

references
References top

Han, L.-J., Yang, S.-P., Wang, D.-Q. & Xia, H.-T. (2006). Acta Cryst. E62, m2607–m2609.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97, SHELXL97 and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.