Tris(ethyl­enediamine)zinc(II) dichloride monohydrate

Cheng, L.; Sun, Y.-Y.; Zhang, Y.-W.; Xu, G.

doi:10.1107/S1600536808027979

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1246

doi:10.1107/S1600536808027979

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Tris(ethylenediamine)zinc(II) dichloride monohydrate

Lin Cheng,^a ^* Yan-Yan Sun,^a Ya-Wen Zhang ^a and Gang Xu ^b

^aDepartment of Chemistry and Chemical Engineering, Southeast University, Nanjing, People's Republic of China, and ^bDepartment of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, People's Republic of China
^*Correspondence e-mail: cep02chl@yahoo.com.cn

(Received 29 August 2008; accepted 2 September 2008; online 6 September 2008)

The asymmetric unit of the title compound, [Zn(C₂H₈N₂)₃]Cl₂·H₂O, contains a discrete [Zn(C₂H₈N₂)₃]²⁺ cation with a distorted octahedral geometry around Zn, two uncoordinated chloride ions and one water molecule. The crystal structure exhibits N—H⋯O, N—H⋯Cl and O—H⋯O hydrogen bonds.

Related literature

For related structures, see: Bernhardt & Riley (2003 ); Cernak et al. (1984 ); Emsley et al. (1989 ); Muralikrishna et al. (1983 ); Nesterova et al. (2006 ); Wu et al. (2001 ).

Experimental

Crystal data

[Zn(C₂H₈N₂)₃]Cl₂·H₂O
M_r = 334.60
Monoclinic, P 2₁ /c
a = 8.8165 (10) Å
b = 11.9379 (14) Å
c = 14.4043 (17) Å
β = 92.804 (2)°
V = 1514.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.97 mm⁻¹
T = 293 (2) K
0.25 × 0.22 × 0.16 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.639, T_max = 0.744
11550 measured reflections
2975 independent reflections
2511 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.085
S = 1.10
2975 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯Cl2ⁱ	0.90	2.86	3.739 (3)	165
N2—H2C⋯Cl1	0.90	2.50	3.363 (3)	162
N2—H2D⋯Cl2ⁱⁱ	0.90	2.48	3.332 (2)	158
N3—H3C⋯O1Wⁱⁱⁱ	0.90	2.27	3.159 (3)	169
N3—H3D⋯Cl2	0.90	2.73	3.605 (3)	165
N4—H4C⋯O1W^iv	0.90	2.39	3.260 (3)	164
N4—H4D⋯Cl1	0.90	2.52	3.375 (3)	159
N5—H5D⋯Cl2ⁱ	0.90	2.57	3.420 (3)	158
N6—H6C⋯Cl1^iv	0.90	2.44	3.309 (3)	161
N6—H6D⋯Cl2	0.90	2.58	3.471 (3)	172
O1W—H1WA⋯Cl1	0.85	2.25	3.097 (3)	171
O1W—H1WB⋯Cl2^v	0.85	2.34	3.187 (3)	180
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) x, y-1, z.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027979/bt2779sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027979/bt2779Isup2.hkl

checkCIF report

Comment top

The preparation of complexes including different stereoisomers is a fascinating and promising means. There are many complexes including [Zn(en)₃]²⁺ cation (en = ethylenediamine), which have been reported, due that [Zn(en)₃]²⁺ cation has two simple and intuitive stereoisomers (Bernhardt et al., 2003; Cernak et al., 1984; Emsley et al., 1989; Muralikrishna et al., 1983; Nesterova et al., 2006; Wu et al., 2001). Different from the similar compound [Zn(en)₃]Cl₂.2H₂O (Muralikrishna et al., 1983; Wu et al., 2001), here, we report a salt [Zn(en)₃]Cl₂.H₂O. In the asymmetric unit of the salt, there are only one crystal water molecule.

The asymmetric unit of the title salt, [Zn(en)₃]Cl₂.H₂O, contains a discrete [Zn(en)₃]²⁺ cation, two uncoordinated chloride ions and one water molecule. The Zn(II) ion displays a distorted octahedral geometry, being surrounded by three en ligands. The Zn···N distances are between 2.159 (2) and 2.220 (2) Å. Each en acts as a chelating bidentate ligand. In crystal, the [Zn(en)₃]²⁺ cations, chloride ions and the crystal water are linked together by N—H···O, N—H···Cl and O—H···Cl hydrogen bonds (Table 2).

Related literature top

For related structures, see: Bernhardt et al. (2003); Cernak et al. (1984); Emsley et al. (1989); Muralikrishna et al. (1983); Nesterova et al. (2006); Wu et al. (2001).

Experimental top

To a solution of ZnCl₂.2H₂O (0.172 g, 1 mmol) in CH₃OH (5 ml), an aqueous solution (5 ml) of bib (bib = 1,3-bis(4,5-Dihydro-1H-imidazol-2-yl)benzene) (0.214 g, 1 mmol) was added. After the mixture was stirred for half an hour, a white precipitate formed. 3 ml en was added to the mixture and the precipitate disappeared. Then the mixture was stirred for an hour and filtered. The filtrate was allowed to evaporate slowly at room temperature. After 3 weeks, colorless block shaped crystals were obtained in 40% yield (0.034 g) based on Zn(II).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound with 30% displacement ellipsoids.
	Fig. 2. Partial packing diagram. The H atoms bonded to C atoms are omitted for clarity.

Tris(ethylenediamine)zinc(II) dichloride monohydrate top

Crystal data top

[Zn(C₂H₈N₂)₃]Cl₂·H₂O	F(000) = 704
M_r = 334.60	D_x = 1.468 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 783 reflections
a = 8.8165 (10) Å	θ = 2.5–28.0°
b = 11.9379 (14) Å	µ = 1.97 mm⁻¹
c = 14.4043 (17) Å	T = 293 K
β = 92.804 (2)°	Block, colorless
V = 1514.2 (3) Å³	0.25 × 0.22 × 0.16 mm
Z = 4

Data collection top

Bruker APEX CCD diffractometer	2975 independent reflections
Radiation source: fine-focus sealed tube	2511 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scan	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −10→10
T_min = 0.639, T_max = 0.744	k = −14→14
11550 measured reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0384P)² + 0.5868P] where P = (F_o² + 2F_c²)/3
2975 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Zn(C₂H₈N₂)₃]Cl₂·H₂O	V = 1514.2 (3) Å³
M_r = 334.60	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8165 (10) Å	µ = 1.97 mm⁻¹
b = 11.9379 (14) Å	T = 293 K
c = 14.4043 (17) Å	0.25 × 0.22 × 0.16 mm
β = 92.804 (2)°

Data collection top

Bruker APEX CCD diffractometer	2975 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2511 reflections with I > 2σ(I)
T_min = 0.639, T_max = 0.744	R_int = 0.030
11550 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.10	Δρ_max = 0.39 e Å⁻³
2975 reflections	Δρ_min = −0.27 e Å⁻³
145 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 > 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

	x	y	z	U_iso*/U_eq
Zn1	0.24154 (3)	0.55616 (3)	0.20878 (2)	0.03553 (12)
Cl1	0.31636 (9)	0.23340 (7)	0.36125 (6)	0.0567 (2)
Cl2	0.20561 (8)	0.87644 (7)	0.38972 (5)	0.0505 (2)
C1	0.3870 (3)	0.3760 (3)	0.1009 (2)	0.0555 (8)
H1A	0.4452	0.3450	0.1538	0.067*
H1B	0.4297	0.3480	0.0446	0.067*
C2	0.2244 (4)	0.3402 (3)	0.1041 (2)	0.0540 (8)
H2A	0.1681	0.3659	0.0486	0.065*
H2B	0.2186	0.2591	0.1058	0.065*
C3	0.1673 (4)	0.5327 (3)	0.4086 (2)	0.0507 (8)
H3A	0.1431	0.4536	0.4034	0.061*
H3B	0.1264	0.5610	0.4653	0.061*
C4	0.3359 (4)	0.5484 (3)	0.4120 (2)	0.0557 (9)
H4A	0.3601	0.6273	0.4192	0.067*
H4B	0.3816	0.5085	0.4649	0.067*
C5	0.0887 (4)	0.7490 (3)	0.1124 (2)	0.0565 (9)
H5A	0.0391	0.7783	0.1659	0.068*
H5B	0.0411	0.7824	0.0569	0.068*
C6	0.2557 (4)	0.7787 (3)	0.1193 (2)	0.0508 (8)
H6A	0.3040	0.7535	0.0640	0.061*
H6B	0.2676	0.8594	0.1238	0.061*
N1	0.3960 (3)	0.4984 (2)	0.10299 (17)	0.0465 (6)
H1C	0.4885	0.5300	0.1105	0.070*
H1D	0.3684	0.5262	0.0466	0.070*
N2	0.1568 (3)	0.3873 (2)	0.18697 (16)	0.0419 (6)
H2C	0.1778	0.3383	0.2333	0.063*
H2D	0.0546	0.3854	0.1839	0.063*
N3	0.0993 (3)	0.5935 (2)	0.32796 (16)	0.0443 (6)
H3C	−0.0010	0.5790	0.3232	0.067*
H3D	0.1079	0.6675	0.3389	0.067*
N4	0.3974 (3)	0.5059 (2)	0.32603 (16)	0.0445 (6)
H4C	0.4947	0.5276	0.3223	0.067*
H4D	0.3872	0.4312	0.3204	0.067*
N5	0.0720 (3)	0.6272 (2)	0.10862 (16)	0.0456 (6)
H5C	−0.0218	0.6039	0.1214	0.068*
H5D	0.0933	0.6075	0.0504	0.068*
N6	0.3279 (3)	0.7250 (2)	0.20173 (16)	0.0444 (6)
H6C	0.4288	0.7342	0.1982	0.067*
H6D	0.3054	0.7678	0.2506	0.067*
O1W	0.2475 (3)	0.0426 (2)	0.21973 (17)	0.0692 (7)
H1WA	0.2630	0.1002	0.2536	0.104*
H1WB	0.2361	−0.0020	0.2649	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03116 (18)	0.0416 (2)	0.03389 (18)	−0.00316 (13)	0.00251 (12)	0.00012 (13)
Cl1	0.0520 (5)	0.0563 (5)	0.0622 (5)	0.0042 (4)	0.0079 (4)	0.0108 (4)
Cl2	0.0449 (4)	0.0597 (5)	0.0467 (4)	0.0018 (3)	0.0009 (3)	−0.0014 (4)
C1	0.0461 (18)	0.073 (2)	0.0480 (18)	0.0078 (16)	0.0089 (14)	−0.0111 (17)
C2	0.0550 (19)	0.056 (2)	0.0503 (19)	−0.0051 (16)	0.0010 (15)	−0.0111 (16)
C3	0.0565 (19)	0.061 (2)	0.0348 (15)	0.0002 (16)	0.0076 (14)	−0.0003 (14)
C4	0.0529 (19)	0.073 (2)	0.0403 (17)	0.0025 (16)	−0.0075 (14)	−0.0069 (16)
C5	0.056 (2)	0.060 (2)	0.0534 (19)	0.0148 (16)	0.0015 (15)	0.0061 (16)
C6	0.067 (2)	0.0420 (18)	0.0440 (17)	−0.0034 (15)	0.0052 (15)	0.0025 (14)
N1	0.0359 (13)	0.0597 (17)	0.0444 (14)	−0.0059 (12)	0.0072 (10)	−0.0020 (12)
N2	0.0349 (12)	0.0484 (15)	0.0425 (13)	−0.0093 (11)	0.0032 (10)	−0.0006 (11)
N3	0.0368 (13)	0.0514 (15)	0.0453 (14)	−0.0006 (11)	0.0072 (10)	−0.0015 (12)
N4	0.0354 (13)	0.0527 (16)	0.0451 (14)	−0.0013 (11)	−0.0023 (10)	−0.0031 (12)
N5	0.0357 (13)	0.0582 (17)	0.0426 (13)	−0.0029 (11)	−0.0004 (10)	0.0052 (12)
N6	0.0407 (13)	0.0467 (15)	0.0461 (14)	−0.0083 (11)	0.0042 (11)	−0.0033 (12)
O1W	0.0747 (18)	0.0651 (17)	0.0678 (16)	0.0051 (12)	0.0032 (14)	0.0022 (12)

Geometric parameters (Å, º) top

Zn1—N6	2.158 (2)	C5—C6	1.513 (5)
Zn1—N2	2.167 (2)	C5—H5A	0.9700
Zn1—N5	2.196 (2)	C5—H5B	0.9700
Zn1—N1	2.203 (2)	C6—N6	1.467 (4)
Zn1—N4	2.208 (2)	C6—H6A	0.9700
Zn1—N3	2.220 (2)	C6—H6B	0.9700
C1—N1	1.464 (4)	N1—H1C	0.9000
C1—C2	1.498 (4)	N1—H1D	0.9000
C1—H1A	0.9700	N2—H2C	0.9000
C1—H1B	0.9700	N2—H2D	0.9000
C2—N2	1.472 (4)	N3—H3C	0.9000
C2—H2A	0.9700	N3—H3D	0.9000
C2—H2B	0.9700	N4—H4C	0.9000
C3—N3	1.472 (4)	N4—H4D	0.9000
C3—C4	1.496 (4)	N5—H5C	0.9000
C3—H3A	0.9700	N5—H5D	0.9000
C3—H3B	0.9700	N6—H6C	0.9000
C4—N4	1.466 (4)	N6—H6D	0.9000
C4—H4A	0.9700	O1W—H1WA	0.8500
C4—H4B	0.9700	O1W—H1WB	0.8503
C5—N5	1.463 (4)

N6—Zn1—N2	168.95 (9)	H5A—C5—H5B	108.3
N6—Zn1—N5	80.73 (9)	N6—C6—C5	109.4 (2)
N2—Zn1—N5	92.59 (9)	N6—C6—H6A	109.8
N6—Zn1—N1	91.62 (9)	C5—C6—H6A	109.8
N2—Zn1—N1	80.16 (9)	N6—C6—H6B	109.8
N5—Zn1—N1	95.18 (9)	C5—C6—H6B	109.8
N6—Zn1—N4	94.68 (9)	H6A—C6—H6B	108.2
N2—Zn1—N4	93.19 (9)	C1—N1—Zn1	106.97 (18)
N5—Zn1—N4	170.26 (9)	C1—N1—H1C	117.9
N1—Zn1—N4	93.52 (9)	Zn1—N1—H1C	111.9
N6—Zn1—N3	93.60 (9)	C1—N1—H1D	109.7
N2—Zn1—N3	95.45 (9)	Zn1—N1—H1D	111.1
N5—Zn1—N3	92.20 (9)	H1C—N1—H1D	99.1
N1—Zn1—N3	171.56 (9)	C2—N2—Zn1	108.81 (18)
N4—Zn1—N3	79.46 (9)	C2—N2—H2C	106.0
N1—C1—C2	109.6 (3)	Zn1—N2—H2C	116.1
N1—C1—H1A	109.8	C2—N2—H2D	113.2
C2—C1—H1A	109.8	Zn1—N2—H2D	111.6
N1—C1—H1B	109.8	H2C—N2—H2D	100.9
C2—C1—H1B	109.8	C3—N3—Zn1	106.68 (18)
H1A—C1—H1B	108.2	C3—N3—H3C	109.1
N2—C2—C1	110.0 (2)	Zn1—N3—H3C	119.5
N2—C2—H2A	109.7	C3—N3—H3D	108.6
C1—C2—H2A	109.7	Zn1—N3—H3D	106.6
N2—C2—H2B	109.7	H3C—N3—H3D	106.0
C1—C2—H2B	109.7	C4—N4—Zn1	108.07 (17)
H2A—C2—H2B	108.2	C4—N4—H4C	110.2
N3—C3—C4	109.3 (3)	Zn1—N4—H4C	115.8
N3—C3—H3A	109.8	C4—N4—H4D	112.3
C4—C3—H3A	109.8	Zn1—N4—H4D	98.3
N3—C3—H3B	109.8	H4C—N4—H4D	111.7
C4—C3—H3B	109.8	C5—N5—Zn1	107.18 (17)
H3A—C3—H3B	108.3	C5—N5—H5C	113.0
N4—C4—C3	109.7 (2)	Zn1—N5—H5C	110.4
N4—C4—H4A	109.7	C5—N5—H5D	105.6
C3—C4—H4A	109.7	Zn1—N5—H5D	110.2
N4—C4—H4B	109.7	H5C—N5—H5D	110.2
C3—C4—H4B	109.7	C6—N6—Zn1	107.84 (18)
H4A—C4—H4B	108.2	C6—N6—H6C	107.0
N5—C5—C6	109.4 (2)	Zn1—N6—H6C	118.0
N5—C5—H5A	109.8	C6—N6—H6D	106.3
C6—C5—H5A	109.8	Zn1—N6—H6D	113.7
N5—C5—H5B	109.8	H6C—N6—H6D	103.4
C6—C5—H5B	109.8	H1WA—O1W—H1WB	95.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl2ⁱ	0.90	2.86	3.739 (3)	165
N2—H2C···Cl1	0.90	2.50	3.363 (3)	162
N2—H2D···Cl2ⁱⁱ	0.90	2.48	3.332 (2)	158
N3—H3C···O1Wⁱⁱⁱ	0.90	2.27	3.159 (3)	169
N3—H3D···Cl2	0.90	2.73	3.605 (3)	165
N4—H4C···O1W^iv	0.90	2.39	3.260 (3)	164
N4—H4D···Cl1	0.90	2.52	3.375 (3)	159
N5—H5D···Cl2ⁱ	0.90	2.57	3.420 (3)	158
N6—H6C···Cl1^iv	0.90	2.44	3.309 (3)	161
N6—H6D···Cl2	0.90	2.58	3.471 (3)	172
O1W—H1WA···Cl1	0.85	2.25	3.097 (3)	171
O1W—H1WB···Cl2^v	0.85	2.34	3.187 (3)	180

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Zn(C₂H₈N₂)₃]Cl₂·H₂O
M_r	334.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.8165 (10), 11.9379 (14), 14.4043 (17)
β (°)	92.804 (2)
V (Å³)	1514.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.97
Crystal size (mm)	0.25 × 0.22 × 0.16

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.639, 0.744
No. of measured, independent and observed [I > 2σ(I)] reflections	11550, 2975, 2511
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.085, 1.10
No. of reflections	2975
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.27

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS (Sheldrick, 2008), SHELXL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl2ⁱ	0.90	2.86	3.739 (3)	164.8
N2—H2C···Cl1	0.90	2.50	3.363 (3)	161.6
N2—H2D···Cl2ⁱⁱ	0.90	2.48	3.332 (2)	157.5
N3—H3C···O1Wⁱⁱⁱ	0.90	2.27	3.159 (3)	168.6
N3—H3D···Cl2	0.90	2.73	3.605 (3)	165.4
N4—H4C···O1W^iv	0.90	2.39	3.260 (3)	163.5
N4—H4D···Cl1	0.90	2.52	3.375 (3)	158.8
N5—H5D···Cl2ⁱ	0.90	2.57	3.420 (3)	158.1
N6—H6C···Cl1^iv	0.90	2.44	3.309 (3)	161.3
N6—H6D···Cl2	0.90	2.58	3.471 (3)	172.1
O1W—H1WA···Cl1	0.85	2.25	3.097 (3)	170.9
O1W—H1WB···Cl2^v	0.85	2.34	3.187 (3)	179.6

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) x, y−1, z.

Acknowledgements

The authors thank the Program for Young Excellent Talents in Southeast University for financial support.

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