Bis[(4-chloro­phen­oxy)acetato-κO](ethyl­enedi­amine-κ2N,N′)zinc

Ashurov, J.M.; Ibragimov, A.B.; Ibragimov, B.T.

doi:10.1107/S2414314618012506

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 9| September 2018| x181250

https://doi.org/10.1107/S2414314618012506

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Bis[(4-chlorophenoxy)acetato-κO](ethylenediamine-κ²N,N′)zinc

Jamshid Mengnorovich Ashurov,^a ^* Aziz Bakhtiyarovich Ibragimov ^b and Bakhtiyar Tulyaganovich Ibragimov ^a

^aInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek Str. 83, Tashkent 700125, Uzbekistan, and ^bInstitute of General and Inorganic Chemistry of Uzbekistan Academy of Sciences, M. Ulugbek Str. 77a, Tashkent 100170, Uzbekistan
^*Correspondence e-mail: atom.uz@mail.ru

Edited by M. Weil, Vienna University of Technology, Austria (Received 28 August 2018; accepted 4 September 2018; online 11 September 2018)

The mononuclear title complex, [Zn(C₈H₆ClO₃)₂(C₂H₈N₂)], was obtained by the reaction of zinc(II) acetate dihydrate with p-chlorophenoxyacetic acid (pCPA) and ethylenediamine (EDA) in a water/ethanol mixture. The Zn^II cation has a distorted tetrahedral coordination sphere involving two carboxylate O atoms of two monodentate pCPA ligands and two N atoms of one chelating EDA ligand. The pCPA ligands coordinate asymmetrically to the Zn^II cation with two different Zn—O distances of 1.967 (3) and 1.978 (3) Å. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming chains propagating parallel to [100]. These chains are linked by C—H⋯O hydrogen bonds, C—H⋯π stacking and Cl⋯Cl interactions, generating a three-dimensional supramolecular network.

Keywords: crystal structure; p-chlorophenoxyacetic acid; ethylenediamine; hydrogen bonding.

CCDC reference: 1865841

Structure description

Phenoxyacetic acid (pCPA) and its derivatives are biologically active compounds which are widely used as herbicides and plant-growth substances. The interaction of metal ions with pCPA results in the formation of complexes in which it demonstrates monodentate (Ashurov et al., 2012 ; Ma et al., 2013 , 2014 ; Li et al., 2014 ) and bidentate (Li et al., 2014; Smith et al., 1981 ; Sun et al., 2007 ) coordination. pCPA ligands can also show bridging properties (Liwporncharoenvong & Luck, 2005 ; Li et al., 2013 ; Jin et al., 2015 ; An et al., 2002 ) and form chain structures (Wang et al., 2006 , 2008 ; Li et al., 2013). Ethylenediamine (EDA) ligands can coordinate to metal ions in a monodentate fashion (Xue et al., 2016 ; Mitzinger et al., 2016 ; Zhang et al., 2009 ; Fanizzi et al., 1984 ; Saidi et al., 2013 ) and in some complexes behave as bridging ligands (Binnemans et al., 2013 ; House & Steel, 1999 ; Bratsos et al., 2011 ; Doring & Jones, 2013 ; Kuhn et al., 2008 ). In many cases, EDA demonstrates a chelating property. There are metal complexes in which noncoordinating EDA molecules are situated in the outer sphere (Peipei et al., 2017 ; Tian et al., 2017 ; Mirzaei et al., 2014 ). A search in the Cambridge Structural Database (CSD; Groom et al., 2016 ) revealed that crystal structures have been reported for complexes of pCPA and EDA with many metal ions. However, no mixed-ligand metal complex including pCPA and EDA is documented in the CSD. Here, the synthesis and structure of the related title compound bis[(4-chlorophenoxy)acetato-κO](ethylenediamine-κ²N,N′)zinc is described.

The asymmetric unit of the title compound consists of a mononuclear complex of formula [Zn(C₈H₇ClO₃)₂(C₂H₈N₂)], as shown in Fig. 1. The coordination polyhedron of the Zn^II cation is a distorted tetrahedron defined by an N₂O₂ coordination set. The distortion is indicated by bond angles O2—Zn1—O2′ [99.47 (11)°], O2—Zn1—N1 [117.37 (11)°], O2—Zn1—N2 [114.42 (12)°], O2′—Zn1—N1 [119.57 (13)°], O2′—Zn1—N2 [122.20 (12)°] and N1—Zn1—N2 [85.14 (13)°]. The dihedral angle between the N1/Zn1/N2 plane and the O2/Zn1/O2′ plane is 87.60 (16)°. The Zn^II cation is coordinated by one EDA molecule, which acts as an N,N′-chelating ligand. The Zn1—N1 and Zn1—N2 distances are 2.041 (4) and 2.052 (3) Å, respectively. The bidentate coordination of the EDA ligand results in the formation of a five-membered chelate ring with an internal angle of 116.0 (15)° for N1—Zn1—N2. The N1—C9—C10—N2 torsion angle within the EDA molecule is −53.0 (4)°. The two pCPA ligands are asymmetrically coordinated to the Zn^II cation, with Zn—O distances of 1.967 (3) and 1.978 (3) Å. The dihedral angle between the N1/Zn/N2 plane and the O2/Zn/O2′ plane is 87.61 (7)°. In both pCPA ligands, the oxyacetate group and the aromatic ring are not perfectly coplanar, the torsion angles being −174.2 (3) (C1—O1—C7—C8) and −170.8 (3)° (C1′—O1′—C7′—C8′). The dihedral angles between the acetate and 4-chlorophenoxy least-squares planes in the two independent ligands are 5.985 (3) and 5.513 (3)°.

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. Unlabelled atoms of the second cCPA ligand are related to the first by a prime character but are not crystallographically equivalent.

In the crystal, molecules are linked by N—H⋯O hydrogen bonds (Table 1 and Fig. 2), forming chains propagating parallel to [100] (Figs. 2 and 3). The N—H⋯O hydrogen-bonding interactions between amine donor groups and carboxylate acceptors groups result in R₄²(12) ring motifs. The chains are linked by C—H⋯O hydrogen bonds (Table 1), forming a sheet structure extending parallel to (010) (Fig. 3). The molecules are further linked by C—H⋯π stacking [3.438 (3) Å] between benzene rings and methylene groups of pCPA, and by Cl1⋯Cl1^i,ii interactions {3.438 (2) [symmetry code: (i) −x + 4, −y + 1, −z] and 3.801(3) Å [symmetry code: (ii) −x + 3, −y + 1, −z]}, generating a three-dimensional supramolecular network.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O3′ⁱ	0.89	2.06	2.931 (4)	166
N2—H2B⋯O3ⁱⁱ	0.89	2.08	2.950 (4)	167
C3—H3⋯O3′ⁱⁱⁱ	0.93	2.59	3.346 (5)	139
C3′—H3′⋯O3^iv	0.93	2.50	3.314 (5)	146
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) $[x+{\script{3\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x-{\script{3\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
Formation of chains and hydrogen bonds in the title complex. Hydrogen bonds are shown as dashed lines.

Figure 3
The packing of the molecules in the title complex in a view along [010]. Intermolecular hydrogen bonding is shown as dashed red lines.

Synthesis and crystallization

To an aqueous solution (2.5 ml) of Zn(CH₃COO)₂ (0.049 g, 0.268 mmol) was added slowly under constant stirring an ethanol solution (5 ml) containing EDA (0.016 g) and pCPA (0.1 g, 0.536 mmol). Colourless crystals were obtained by solvent evaporation at room temperature after one week (yield 75%). Elemental analysis calculated for C₁₈H₂₀Cl₂N₂O₆Zn: C 43.53, H 4.06, N 5.64%; found: C 43.58, H 4.12, N 5.69%.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Zn(C₈H₆ClO₃)₂(C₂H₈N₂)]
M_r	496.63
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.6621 (11), 19.366 (13), 18.816 (4)
β (°)	96.09 (2)
V (Å³)	2051.6 (15)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	4.40
Crystal size (mm)	0.42 × 0.36 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ )
T_min, T_max	0.569, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8985, 4125, 2146
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.123, 0.84
No. of reflections	4125
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.97, −0.35
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ), olex2.solve (Bourhis et al., 2015 ), SHELXL2014 (Sheldrick, 2015 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1865841

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618012506/wm4086sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618012506/wm4086Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis[(4-chlorophenoxy)acetato-κO](ethylenediamine-κ²N,N')zinc top

Crystal data top

[Zn(C₈H₆ClO₃)₂(C₂H₈N₂)]	F(000) = 1016
M_r = 496.63	D_x = 1.608 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 5.6621 (11) Å	Cell parameters from 568 reflections
b = 19.366 (13) Å	θ = 3.3–75.7°
c = 18.816 (4) Å	µ = 4.40 mm⁻¹
β = 96.09 (2)°	T = 293 K
V = 2051.6 (15) Å³	Block, colorless
Z = 4	0.42 × 0.36 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	4125 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2146 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 10.2576 pixels mm^-1	θ_max = 75.3°, θ_min = 3.3°
ω scans	h = −6→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −14→24
T_min = 0.569, T_max = 1.000	l = −23→23
8985 measured reflections

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0653P)²] where P = (F_o² + 2F_c²)/3
S = 0.84	(Δ/σ)_max < 0.001
4125 reflections	Δρ_max = 0.97 e Å⁻³
262 parameters	Δρ_min = −0.34 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.48309 (8)	0.70588 (3)	0.38879 (3)	0.05115 (17)
Cl1	1.7835 (2)	0.54592 (7)	0.03685 (7)	0.0914 (4)
Cl1'	−0.8303 (3)	0.54629 (7)	0.73405 (8)	0.1022 (5)
O2	0.6929 (4)	0.64544 (13)	0.33966 (14)	0.0542 (7)
O2'	0.2828 (4)	0.63502 (13)	0.42866 (14)	0.0569 (7)
O3	0.8426 (5)	0.74137 (14)	0.29750 (16)	0.0583 (7)
O3'	0.1265 (5)	0.72723 (13)	0.47574 (16)	0.0602 (8)
O1	1.1489 (5)	0.67189 (13)	0.22793 (16)	0.0692 (9)
O1'	−0.1830 (5)	0.65479 (15)	0.53761 (19)	0.0882 (11)
N1	0.6398 (5)	0.78062 (16)	0.45419 (19)	0.0613 (9)
H1A	0.5691	0.7834	0.4941	0.074*
H1B	0.7926	0.7708	0.4658	0.074*
N2	0.3406 (5)	0.78667 (15)	0.32804 (18)	0.0588 (9)
H2A	0.4137	0.7911	0.2887	0.071*
H2B	0.1867	0.7794	0.3152	0.071*
C8	0.8322 (6)	0.6779 (2)	0.3031 (2)	0.0492 (9)
C1	1.2919 (7)	0.6383 (2)	0.1844 (2)	0.0540 (10)
C8'	0.1401 (6)	0.6639 (2)	0.4674 (2)	0.0504 (10)
C7	0.9894 (6)	0.63128 (19)	0.2646 (2)	0.0518 (10)
H7A	1.0791	0.6011	0.2987	0.062*
H7B	0.8926	0.6027	0.2307	0.062*
C7'	−0.0217 (6)	0.6143 (2)	0.5016 (2)	0.0548 (10)
H7'A	−0.1083	0.5857	0.4654	0.066*
H7'B	0.0709	0.5845	0.5353	0.066*
C6	1.3034 (7)	0.5669 (2)	0.1764 (2)	0.0618 (12)
H6	1.2102	0.5381	0.2013	0.074*
C2	1.4358 (7)	0.6799 (2)	0.1478 (2)	0.0615 (11)
H2	1.4320	0.7275	0.1545	0.074*
C3	1.5848 (7)	0.6527 (2)	0.1017 (2)	0.0602 (11)
H3	1.6782	0.6812	0.0763	0.072*
C2'	−0.4549 (7)	0.6694 (2)	0.6210 (2)	0.0643 (12)
H2'	−0.4363	0.7167	0.6151	0.077*
C3'	−0.6059 (7)	0.6452 (2)	0.6682 (2)	0.0627 (12)
H3'	−0.6882	0.6757	0.6948	0.075*
C4'	−0.6321 (7)	0.5753 (2)	0.6751 (2)	0.0616 (11)
C1'	−0.3307 (7)	0.6237 (2)	0.5824 (2)	0.0608 (11)
C6'	−0.3578 (8)	0.5530 (2)	0.5898 (2)	0.0659 (12)
H6'	−0.2745	0.5223	0.5637	0.079*
C5'	−0.5131 (8)	0.5287 (2)	0.6373 (2)	0.0661 (12)
H5'	−0.5353	0.4816	0.6431	0.079*
C4	1.5910 (7)	0.5819 (2)	0.0942 (2)	0.0613 (11)
C9	0.6155 (7)	0.8462 (2)	0.4149 (3)	0.0699 (13)
H9A	0.7391	0.8500	0.3832	0.084*
H9B	0.6325	0.8845	0.4483	0.084*
C5	1.4556 (8)	0.5395 (2)	0.1306 (2)	0.0671 (13)
H5	1.4649	0.4919	0.1249	0.081*
C10	0.3740 (7)	0.8491 (2)	0.3721 (2)	0.0690 (13)
H10A	0.2509	0.8519	0.4041	0.083*
H10B	0.3632	0.8897	0.3418	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0394 (2)	0.0495 (3)	0.0668 (4)	0.0015 (3)	0.0163 (2)	−0.0043 (3)
Cl1	0.0874 (9)	0.1086 (10)	0.0866 (9)	0.0091 (7)	0.0490 (7)	−0.0154 (8)
Cl1'	0.1095 (11)	0.1037 (10)	0.1036 (11)	−0.0081 (9)	0.0589 (9)	0.0235 (9)
O2	0.0457 (15)	0.0576 (15)	0.0637 (18)	0.0021 (12)	0.0256 (13)	−0.0020 (14)
O2'	0.0452 (14)	0.0623 (16)	0.0669 (19)	−0.0009 (13)	0.0236 (13)	−0.0063 (15)
O3	0.0477 (16)	0.0576 (16)	0.073 (2)	0.0030 (14)	0.0237 (14)	0.0016 (16)
O3'	0.0441 (15)	0.0581 (16)	0.082 (2)	−0.0018 (12)	0.0249 (14)	−0.0045 (15)
O1	0.0669 (19)	0.0579 (16)	0.091 (2)	−0.0050 (14)	0.0453 (17)	−0.0115 (16)
O1'	0.080 (2)	0.0644 (18)	0.133 (3)	0.0086 (16)	0.068 (2)	0.016 (2)
N1	0.0416 (18)	0.071 (2)	0.073 (3)	−0.0009 (16)	0.0118 (16)	−0.013 (2)
N2	0.0435 (17)	0.059 (2)	0.076 (2)	0.0024 (16)	0.0179 (16)	0.0044 (19)
C8	0.039 (2)	0.058 (2)	0.052 (3)	−0.0022 (18)	0.0112 (18)	−0.008 (2)
C1	0.050 (2)	0.059 (2)	0.056 (3)	0.0027 (19)	0.0201 (19)	−0.006 (2)
C8'	0.037 (2)	0.061 (2)	0.054 (3)	0.0005 (18)	0.0092 (18)	0.000 (2)
C7	0.052 (2)	0.054 (2)	0.052 (2)	0.0012 (19)	0.0202 (19)	−0.003 (2)
C7'	0.049 (2)	0.062 (2)	0.056 (3)	0.0040 (19)	0.0186 (19)	−0.001 (2)
C6	0.065 (3)	0.057 (2)	0.068 (3)	−0.006 (2)	0.031 (2)	−0.009 (2)
C2	0.053 (2)	0.060 (2)	0.075 (3)	0.003 (2)	0.022 (2)	0.004 (2)
C3	0.054 (2)	0.074 (3)	0.056 (3)	0.003 (2)	0.024 (2)	0.007 (2)
C2'	0.061 (3)	0.050 (2)	0.086 (3)	−0.006 (2)	0.028 (2)	−0.005 (2)
C3'	0.059 (3)	0.067 (3)	0.066 (3)	−0.002 (2)	0.021 (2)	−0.008 (2)
C4'	0.058 (3)	0.071 (3)	0.059 (3)	−0.003 (2)	0.019 (2)	0.007 (2)
C1'	0.054 (2)	0.062 (2)	0.071 (3)	−0.002 (2)	0.024 (2)	0.002 (2)
C6'	0.066 (3)	0.057 (2)	0.078 (3)	0.011 (2)	0.020 (2)	0.000 (2)
C5'	0.067 (3)	0.060 (2)	0.072 (3)	−0.005 (2)	0.013 (2)	0.011 (2)
C4	0.056 (2)	0.078 (3)	0.052 (3)	0.005 (2)	0.016 (2)	−0.006 (2)
C9	0.055 (3)	0.052 (2)	0.106 (4)	−0.009 (2)	0.027 (3)	−0.020 (3)
C5	0.071 (3)	0.062 (3)	0.073 (3)	−0.002 (2)	0.030 (2)	−0.009 (2)
C10	0.058 (3)	0.051 (2)	0.101 (4)	0.010 (2)	0.028 (3)	0.005 (2)

Geometric parameters (Å, º) top

Zn1—O2	1.967 (2)	C7'—H7'A	0.9700
Zn1—O2'	1.978 (3)	C7'—H7'B	0.9700
Zn1—N1	2.041 (3)	C6—H6	0.9300
Zn1—N2	2.052 (3)	C6—C5	1.386 (5)
Cl1—C4	1.757 (4)	C2—H2	0.9300
Cl1'—C4'	1.752 (4)	C2—C3	1.377 (5)
O2—C8	1.267 (4)	C3—H3	0.9300
O2'—C8'	1.274 (4)	C3—C4	1.379 (6)
O3—C8	1.235 (4)	C2'—H2'	0.9300
O3'—C8'	1.240 (4)	C2'—C3'	1.378 (5)
O1—C1	1.375 (4)	C2'—C1'	1.384 (5)
O1—C7	1.430 (4)	C3'—H3'	0.9300
O1'—C7'	1.428 (4)	C3'—C4'	1.369 (5)
O1'—C1'	1.386 (4)	C4'—C5'	1.370 (6)
N1—H1A	0.8900	C1'—C6'	1.385 (6)
N1—H1B	0.8900	C6'—H6'	0.9300
N1—C9	1.469 (5)	C6'—C5'	1.401 (6)
N2—H2A	0.8900	C5'—H5'	0.9300
N2—H2B	0.8900	C4—C5	1.359 (6)
N2—C10	1.466 (5)	C9—H9A	0.9700
C8—C7	1.506 (5)	C9—H9B	0.9700
C1—C6	1.392 (5)	C9—C10	1.513 (6)
C1—C2	1.381 (5)	C5—H5	0.9300
C8'—C7'	1.516 (5)	C10—H10A	0.9700
C7—H7A	0.9700	C10—H10B	0.9700
C7—H7B	0.9700

O2—Zn1—O2'	99.47 (11)	C5—C6—C1	119.2 (4)
O2—Zn1—N1	117.37 (12)	C5—C6—H6	120.4
O2—Zn1—N2	114.42 (12)	C1—C2—H2	119.2
O2'—Zn1—N1	119.57 (13)	C3—C2—C1	121.6 (4)
O2'—Zn1—N2	122.20 (12)	C3—C2—H2	119.2
N1—Zn1—N2	85.14 (14)	C2—C3—H3	121.0
C8—O2—Zn1	113.7 (2)	C2—C3—C4	117.9 (4)
C8'—O2'—Zn1	109.7 (2)	C4—C3—H3	121.0
C1—O1—C7	118.0 (3)	C3'—C2'—H2'	119.8
C1'—O1'—C7'	120.5 (3)	C3'—C2'—C1'	120.4 (4)
Zn1—N1—H1A	110.2	C1'—C2'—H2'	119.8
Zn1—N1—H1B	110.2	C2'—C3'—H3'	120.7
H1A—N1—H1B	108.5	C4'—C3'—C2'	118.5 (4)
C9—N1—Zn1	107.4 (3)	C4'—C3'—H3'	120.7
C9—N1—H1A	110.2	C3'—C4'—Cl1'	117.4 (3)
C9—N1—H1B	110.2	C3'—C4'—C5'	122.5 (4)
Zn1—N2—H2A	110.3	C5'—C4'—Cl1'	120.0 (3)
Zn1—N2—H2B	110.3	C2'—C1'—O1'	114.5 (4)
H2A—N2—H2B	108.6	C2'—C1'—C6'	120.7 (4)
C10—N2—Zn1	107.1 (3)	C6'—C1'—O1'	124.8 (4)
C10—N2—H2A	110.3	C1'—C6'—H6'	120.7
C10—N2—H2B	110.3	C1'—C6'—C5'	118.7 (4)
O2—C8—C7	113.4 (3)	C5'—C6'—H6'	120.7
O3—C8—O2	125.3 (4)	C4'—C5'—C6'	119.2 (4)
O3—C8—C7	121.3 (3)	C4'—C5'—H5'	120.4
O1—C1—C6	124.9 (4)	C6'—C5'—H5'	120.4
O1—C1—C2	115.9 (4)	C3—C4—Cl1	118.8 (3)
C2—C1—C6	119.2 (4)	C5—C4—Cl1	119.3 (4)
O2'—C8'—C7'	114.4 (3)	C5—C4—C3	121.9 (4)
O3'—C8'—O2'	123.9 (4)	N1—C9—H9A	109.8
O3'—C8'—C7'	121.6 (3)	N1—C9—H9B	109.8
O1—C7—C8	109.8 (3)	N1—C9—C10	109.3 (3)
O1—C7—H7A	109.7	H9A—C9—H9B	108.3
O1—C7—H7B	109.7	C10—C9—H9A	109.8
C8—C7—H7A	109.7	C10—C9—H9B	109.8
C8—C7—H7B	109.7	C6—C5—H5	119.9
H7A—C7—H7B	108.2	C4—C5—C6	120.1 (4)
O1'—C7'—C8'	107.4 (3)	C4—C5—H5	119.9
O1'—C7'—H7'A	110.2	N2—C10—C9	109.1 (3)
O1'—C7'—H7'B	110.2	N2—C10—H10A	109.9
C8'—C7'—H7'A	110.2	N2—C10—H10B	109.9
C8'—C7'—H7'B	110.2	C9—C10—H10A	109.9
H7'A—C7'—H7'B	108.5	C9—C10—H10B	109.9
C1—C6—H6	120.4	H10A—C10—H10B	108.3

Zn1—O2—C8—O3	0.4 (6)	C7—O1—C1—C6	−3.9 (6)
Zn1—O2—C8—C7	−179.0 (2)	C7—O1—C1—C2	177.4 (4)
Zn1—O2'—C8'—O3'	2.5 (5)	C7'—O1'—C1'—C2'	171.9 (4)
Zn1—O2'—C8'—C7'	−179.4 (3)	C7'—O1'—C1'—C6'	−8.1 (7)
Zn1—N1—C9—C10	38.5 (4)	C6—C1—C2—C3	2.2 (7)
Zn1—N2—C10—C9	39.2 (4)	C2—C1—C6—C5	−1.3 (7)
Cl1—C4—C5—C6	179.7 (3)	C2—C3—C4—Cl1	−178.9 (3)
Cl1'—C4'—C5'—C6'	179.2 (4)	C2—C3—C4—C5	0.1 (7)
O2—C8—C7—O1	−176.9 (3)	C3—C4—C5—C6	0.7 (7)
O2'—C8'—C7'—O1'	−174.9 (3)	C2'—C3'—C4'—Cl1'	−178.6 (3)
O3—C8—C7—O1	3.7 (6)	C2'—C3'—C4'—C5'	0.4 (7)
O3'—C8'—C7'—O1'	3.1 (6)	C2'—C1'—C6'—C5'	−0.2 (7)
O1—C1—C6—C5	−180.0 (4)	C3'—C2'—C1'—O1'	−179.2 (4)
O1—C1—C2—C3	−179.0 (4)	C3'—C2'—C1'—C6'	0.8 (7)
O1'—C1'—C6'—C5'	179.8 (4)	C3'—C4'—C5'—C6'	0.2 (7)
N1—C9—C10—N2	−53.0 (4)	C1'—O1'—C7'—C8'	−170.8 (4)
C1—O1—C7—C8	−174.2 (3)	C1'—C2'—C3'—C4'	−0.9 (7)
C1—C6—C5—C4	−0.1 (7)	C1'—C6'—C5'—C4'	−0.3 (7)
C1—C2—C3—C4	−1.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3′ⁱ	0.89	2.06	2.931 (4)	166
N2—H2B···O3ⁱⁱ	0.89	2.08	2.950 (4)	167
C3—H3···O3′ⁱⁱⁱ	0.93	2.59	3.346 (5)	139
C3′—H3′···O3^iv	0.93	2.50	3.314 (5)	146

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

Funding information

Funding for this research was provided by: Center of Science and Technology, Uzbekistan (Grant for Fundamental Research No. BA-FA-F7-004).

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