Poly[[μ-(3-amino­pyridine)-κ2N:N′-μ-chlorido-chlorido(N,N′-dimethyl­formamide-κO)nickel(II)] N,N′-dimethyl­formamide monosolvate]

Yeh, C.-W.; Jou, C.-H.; Tsou, C.-H.; Suen, M.-C.

doi:10.1107/S1600536812036215

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages m1204-m1205

doi:10.1107/S1600536812036215

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Poly[[μ-(3-aminopyridine)-κ²N:N′-μ-chlorido-chlorido(N,N′-dimethylformamide-κO)nickel(II)] N,N′-dimethylformamide monosolvate]

Chun-Wei Yeh,^a Chi-Hsiung Jou,^b Chi-Hui Tsou ^c and Maw-Cherng Suen ^d ^*

^aDepartment of Chemistry, Chung-Yuan Christian University, Jhongli 32023, Taiwan, ^bDepartment of Materials and Textiles, Oriental Institute of Technology, New Taipei City, Taiwan, ^cDepartment of Materials Science and Engineering, National Taiwan University of Science and Technology, Taipei 10607, Taiwan, and ^dDepartment of Applied Cosmetology, Taoyuan Innovation Institute of Technology, Jhongli 32091, Taiwan
^*Correspondence e-mail: sun@tiit.edu.tw

(Received 13 August 2012; accepted 19 August 2012; online 25 August 2012)

The title compound, {[NiCl₂(C₅H₆N₂)(C₃H₇NO)]·C₃H₇NO}_n, is a two-dimensional polymer in which the Ni^II atom is coordinated by two N atoms from two 3-aminopyridine ligands, one O atom from a dimethylformamide (DMF) group, one terminal Cl and two bridging Cl atoms in a distorted octahedral geometry. The Ni^II atoms are bridged by the 3-aminopyridine ligands [Ni⋯N = 6.7048 (3) Å] and Cl⁻ atoms [Ni⋯N = 3.5698 (3) Å], forming (4,4) two-dimensional nets. The DMF solvent molecule and the non-bridged Cl⁻ ions participate in N—H⋯O and N—H⋯Cl hydrogen bonds with the amino groups.

Related literature

For background to coordination polymers, see: Kitagawa et al. (2004 ); Chiang et al. (2008 ); Yeh et al. (2008 , 2009 ); Hsu et al. (2009 ). For related 3-aminopyridine complexes, see: Zhu & Kitagawa (2002 ); Lah & Leban (2005 , 2006 ); Kochel (2006 ); Wu et al. (2005 ); Qian & Huang (2006 ).

Experimental

Crystal data

[NiCl₂(C₅H₆N₂)(C₃H₇NO)]·C₃H₇NO
M_r = 369.92
Monoclinic, P 2₁ /c
a = 10.3684 (2) Å
b = 15.0571 (3) Å
c = 10.0976 (2) Å
β = 103.832 (2)°
V = 1530.70 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 293 K
0.38 × 0.30 × 0.18 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.628, T_max = 1.000
6140 measured reflections
2748 independent reflections
2333 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.058
S = 1.04
2748 reflections
193 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2NA⋯Cl2ⁱ	0.89 (2)	2.60 (2)	3.4869 (16)	176.4 (1)
N2—H2NB⋯O2ⁱⁱ	0.84 (2)	2.11 (2)	2.925 (2)	173.3 (1)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2010 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812036215/xu5609sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036215/xu5609Isup2.hkl

checkCIF report

Comment top

The synthesis of metal coordination polymers has been a subject of intense research due to their interesting structural chemistry and potential applications in gas storage, separation, catalysis, magnetism, luminescence, and drug delivery (Kitagawa et al., 2004). Roles of anion, solvent and ligand comformations in self-assembly of coordination complexes containing polydentate nitrogen ligands are very intersting (Chiang et al., 2008; Yeh et al., 2008; Hsu et al., 2009; Yeh et al., 2009). In the past, the 3-aminopyridine ligands have been subjected to many studies of its coordination ability to structure chemistry (Zhu et al., 2002; Lah & Leban, 2005; Lah & Leban, 2006; Kochel, 2006; Wu et al., 2005; Qian et al., 2006). The Ni²⁺ cations are coordinated with two N atoms from two 3-aminopyridine (L) ligands, one O atom from dimethylformamide group, one terminal Cl and two bridging Cl atoms (Fig. 1). The Ni···Ni distances separated by the bridging Cl^- anions and L groups are 3.5698 (3) and 6.7048 (3) Å, while the unit of dinuclear [Ni₂Cl₂] cores are forming (4,4) polymeric nets (Fig. 2). The co-crystallized DMF molecules and terminal Cl^- ions are interacted with the amino hydrogen atoms forming N—H···O and N—H···Cl inter– and intra–molecular hydrogen bonds (Tab. 1).

Related literature top

For background to coordination polymers, see: Kitagawa et al. (2004); Chiang et al. (2008); Yeh et al. (2008, 2009); Hsu et al. (2009). For related 3-aminopyridine complexes, see: Zhu et al. (2002); Lah & Leban (2005, 2006); Kochel (2006); Wu et al. (2005); Qian et al. (2006).

Experimental top

An aquous solution (5.0 ml) of nickel chloride (1.0 mmol) was layered carefully over a mixed CH₃OH/DMF solution (5.0 ml, 1:1) of 3-aminopyridine (1.0 mmol) in a tube. Green crystals were obtained after several weeks. These were washed with methanol and collected in 72.8% yield.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A portion of the two-dimensional grid. Ellipsoids are drawn at 30% probability level. [Symmetry codes: (i) x,-y + 3/2,z + 1/2;(ii) -x + 1,-y + 1,-z + 1; (iii) x,-y + 3/2,z - 1/2.]
	Fig. 2. The view shows the two-dimensional pleated (4,4) net.

Poly[[µ-(3-aminopyridine)-κ²N:N'-µ-chlorido- chlorido(N,N'-dimethylformamide-κO)nickel(II)] N,N'-dimethylformamide monosolvate] top

Crystal data top

[NiCl₂(C₅H₆N₂)(C₃H₇NO)]·C₃H₇NO	F(000) = 768
M_r = 369.92	D_x = 1.605 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4748 reflections
a = 10.3684 (2) Å	θ = 3.2–29.0°
b = 15.0571 (3) Å	µ = 1.62 mm⁻¹
c = 10.0976 (2) Å	T = 293 K
β = 103.832 (2)°	Plate, green
V = 1530.70 (5) Å³	0.38 × 0.30 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII diffractometer	2748 independent reflections
Radiation source: fine-focus sealed tube	2333 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
phi and ω scans	θ_max = 25.2°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→12
T_min = 0.628, T_max = 1.000	k = −16→18
6140 measured reflections	l = −12→11

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0322P)²] where P = (F_o² + 2F_c²)/3
2748 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.70 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[NiCl₂(C₅H₆N₂)(C₃H₇NO)]·C₃H₇NO	V = 1530.70 (5) Å³
M_r = 369.92	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.3684 (2) Å	µ = 1.62 mm⁻¹
b = 15.0571 (3) Å	T = 293 K
c = 10.0976 (2) Å	0.38 × 0.30 × 0.18 mm
β = 103.832 (2)°

Data collection top

Bruker SMART APEXII diffractometer	2748 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2333 reflections with I > 2σ(I)
T_min = 0.628, T_max = 1.000	R_int = 0.021
6140 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.70 e Å⁻³
2748 reflections	Δρ_min = −0.34 e Å⁻³
193 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
Ni	0.41415 (2)	0.603502 (16)	0.48905 (2)	0.00775 (9)
C1	0.38923 (19)	0.80038 (13)	0.50209 (19)	0.0102 (4)
H1A	0.3489	0.7849	0.5718	0.012*
C2	0.4014 (2)	0.88919 (13)	0.4737 (2)	0.0125 (4)
H2A	0.3717	0.9325	0.5251	0.015*
C3	0.4579 (2)	0.91299 (13)	0.3683 (2)	0.0120 (4)
H3A	0.4655	0.9725	0.3466	0.014*
C4	0.50335 (19)	0.84671 (13)	0.29533 (19)	0.0086 (4)
C5	0.49098 (19)	0.75896 (13)	0.33264 (19)	0.0089 (4)
H5A	0.5242	0.7146	0.2860	0.011*
C6	0.1441 (2)	0.62218 (13)	0.5369 (2)	0.0127 (4)
H6A	0.1190	0.5851	0.4614	0.015*
C7	−0.0851 (2)	0.61693 (15)	0.5540 (3)	0.0222 (5)
H7A	−0.0954	0.5838	0.4709	0.033*
H7B	−0.1451	0.6665	0.5390	0.033*
H7C	−0.1045	0.5793	0.6235	0.033*
C8	0.0852 (2)	0.70808 (15)	0.7160 (2)	0.0185 (5)
H8A	0.1524	0.7493	0.7047	0.028*
H8B	0.1179	0.6734	0.7968	0.028*
H8C	0.0074	0.7401	0.7241	0.028*
C9	0.2418 (2)	1.14619 (14)	0.3491 (3)	0.0210 (5)
H9A	0.2665	1.1173	0.2775	0.025*
C10	0.1142 (2)	1.01507 (16)	0.3680 (3)	0.0342 (6)
H10A	0.1512	0.9948	0.2949	0.051*
H10B	0.0196	1.0210	0.3358	0.051*
H10C	0.1338	0.9730	0.4414	0.051*
C11	0.1376 (3)	1.13771 (16)	0.5363 (2)	0.0274 (6)
H11A	0.1539	1.0943	0.6080	0.041*
H11B	0.0455	1.1541	0.5146	0.041*
H11C	0.1913	1.1893	0.5657	0.041*
N1	0.43323 (16)	0.73532 (11)	0.43310 (16)	0.0090 (4)
N2	0.55335 (18)	0.86856 (12)	0.18049 (17)	0.0093 (4)
H2NA	0.596 (2)	0.9204 (15)	0.190 (2)	0.010 (6)*
H2NB	0.600 (2)	0.8292 (16)	0.160 (2)	0.019 (7)*
N3	0.05143 (17)	0.64924 (11)	0.59758 (17)	0.0140 (4)
N4	0.17122 (19)	1.10045 (12)	0.41599 (19)	0.0212 (4)
O1	0.26235 (14)	0.64348 (8)	0.57502 (14)	0.0120 (3)
O2	0.27851 (16)	1.22267 (10)	0.37064 (17)	0.0267 (4)
Cl1	0.60647 (5)	0.54783 (3)	0.42042 (5)	0.00949 (12)
Cl2	0.26678 (5)	0.56642 (3)	0.27259 (5)	0.01240 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.00809 (14)	0.00705 (14)	0.00920 (14)	−0.00007 (11)	0.00421 (10)	−0.00004 (10)
C1	0.0088 (10)	0.0124 (11)	0.0097 (10)	0.0003 (9)	0.0028 (8)	−0.0004 (8)
C2	0.0141 (11)	0.0122 (11)	0.0117 (10)	0.0013 (9)	0.0038 (9)	−0.0035 (9)
C3	0.0148 (11)	0.0082 (10)	0.0124 (10)	−0.0016 (9)	0.0021 (9)	0.0005 (8)
C4	0.0061 (10)	0.0118 (10)	0.0076 (9)	−0.0013 (8)	0.0008 (8)	0.0007 (8)
C5	0.0065 (10)	0.0109 (10)	0.0091 (9)	0.0014 (8)	0.0015 (8)	−0.0007 (8)
C6	0.0148 (11)	0.0097 (10)	0.0144 (10)	−0.0005 (9)	0.0052 (9)	0.0022 (9)
C7	0.0140 (12)	0.0201 (12)	0.0347 (13)	−0.0027 (10)	0.0104 (10)	−0.0025 (11)
C8	0.0163 (12)	0.0195 (12)	0.0228 (12)	0.0017 (10)	0.0110 (10)	−0.0030 (10)
C9	0.0066 (10)	0.0182 (13)	0.0414 (14)	−0.0015 (10)	0.0121 (10)	−0.0117 (11)
C10	0.0259 (14)	0.0224 (14)	0.0514 (17)	−0.0045 (11)	0.0036 (13)	−0.0057 (13)
C11	0.0332 (14)	0.0287 (14)	0.0242 (13)	0.0007 (12)	0.0145 (11)	0.0035 (11)
N1	0.0074 (8)	0.0099 (8)	0.0090 (8)	0.0008 (7)	0.0008 (7)	0.0002 (7)
N2	0.0117 (9)	0.0057 (9)	0.0118 (9)	0.0007 (8)	0.0055 (7)	−0.0001 (7)
N3	0.0098 (9)	0.0136 (9)	0.0208 (10)	−0.0002 (8)	0.0079 (8)	−0.0010 (8)
N4	0.0225 (11)	0.0159 (10)	0.0262 (10)	0.0018 (9)	0.0075 (9)	0.0009 (8)
O1	0.0110 (7)	0.0116 (7)	0.0148 (7)	−0.0002 (6)	0.0059 (6)	0.0004 (6)
O2	0.0270 (10)	0.0195 (9)	0.0385 (10)	−0.0038 (8)	0.0174 (8)	0.0034 (8)
Cl1	0.0099 (2)	0.0079 (2)	0.0125 (2)	−0.0002 (2)	0.00632 (19)	0.00006 (19)
Cl2	0.0128 (3)	0.0128 (3)	0.0116 (2)	−0.0007 (2)	0.0029 (2)	−0.0008 (2)

Geometric parameters (Å, º) top

Ni—O1	2.0607 (13)	C7—H7B	0.9600
Ni—N1	2.0860 (16)	C7—H7C	0.9600
Ni—N2ⁱ	2.1593 (17)	C8—N3	1.462 (3)
Ni—Cl1	2.4124 (5)	C8—H8A	0.9600
Ni—Cl2	2.4139 (5)	C8—H8B	0.9600
Ni—Cl1ⁱⁱ	2.4833 (5)	C8—H8C	0.9600
C1—N1	1.343 (2)	C9—O2	1.216 (2)
C1—C2	1.380 (3)	C9—N4	1.305 (3)
C1—H1A	0.9300	C9—H9A	0.9300
C2—C3	1.380 (3)	C10—N4	1.449 (3)
C2—H2A	0.9300	C10—H10A	0.9600
C3—C4	1.388 (3)	C10—H10B	0.9600
C3—H3A	0.9300	C10—H10C	0.9600
C4—C5	1.388 (3)	C11—N4	1.454 (3)
C4—N2	1.417 (2)	C11—H11A	0.9600
C5—N1	1.343 (2)	C11—H11B	0.9600
C5—H5A	0.9300	C11—H11C	0.9600
C6—O1	1.236 (2)	N2—Niⁱⁱⁱ	2.1593 (17)
C6—N3	1.322 (3)	N2—H2NA	0.89 (2)
C6—H6A	0.9300	N2—H2NB	0.82 (2)
C7—N3	1.462 (3)	Cl1—Niⁱⁱ	2.4833 (5)
C7—H7A	0.9600

O1—Ni—N1	88.14 (6)	N3—C8—H8A	109.5
O1—Ni—N2ⁱ	88.87 (6)	N3—C8—H8B	109.5
N1—Ni—N2ⁱ	88.32 (7)	H8A—C8—H8B	109.5
O1—Ni—Cl1	171.70 (4)	N3—C8—H8C	109.5
N1—Ni—Cl1	96.57 (5)	H8A—C8—H8C	109.5
N2ⁱ—Ni—Cl1	84.46 (5)	H8B—C8—H8C	109.5
O1—Ni—Cl2	93.85 (4)	O2—C9—N4	126.7 (2)
N1—Ni—Cl2	93.17 (5)	O2—C9—H9A	116.7
N2ⁱ—Ni—Cl2	176.93 (5)	N4—C9—H9A	116.7
Cl1—Ni—Cl2	92.710 (18)	N4—C10—H10A	109.5
O1—Ni—Cl1ⁱⁱ	88.36 (4)	N4—C10—H10B	109.5
N1—Ni—Cl1ⁱⁱ	174.19 (4)	H10A—C10—H10B	109.5
N2ⁱ—Ni—Cl1ⁱⁱ	86.97 (5)	N4—C10—H10C	109.5
Cl1—Ni—Cl1ⁱⁱ	86.372 (17)	H10A—C10—H10C	109.5
Cl2—Ni—Cl1ⁱⁱ	91.690 (18)	H10B—C10—H10C	109.5
N1—C1—C2	122.69 (18)	N4—C11—H11A	109.5
N1—C1—H1A	118.7	N4—C11—H11B	109.5
C2—C1—H1A	118.7	H11A—C11—H11B	109.5
C1—C2—C3	119.24 (19)	N4—C11—H11C	109.5
C1—C2—H2A	120.4	H11A—C11—H11C	109.5
C3—C2—H2A	120.4	H11B—C11—H11C	109.5
C2—C3—C4	118.92 (19)	C5—N1—C1	117.80 (17)
C2—C3—H3A	120.5	C5—N1—Ni	123.02 (13)
C4—C3—H3A	120.5	C1—N1—Ni	119.17 (13)
C3—C4—C5	118.36 (18)	C4—N2—Niⁱⁱⁱ	118.73 (13)
C3—C4—N2	120.29 (18)	C4—N2—H2NA	112.6 (13)
C5—C4—N2	121.23 (18)	Niⁱⁱⁱ—N2—H2NA	97.6 (14)
N1—C5—C4	122.94 (18)	C4—N2—H2NB	112.8 (16)
N1—C5—H5A	118.5	Niⁱⁱⁱ—N2—H2NB	102.9 (16)
C4—C5—H5A	118.5	H2NA—N2—H2NB	111 (2)
O1—C6—N3	123.51 (19)	C6—N3—C7	121.13 (18)
O1—C6—H6A	118.2	C6—N3—C8	120.52 (18)
N3—C6—H6A	118.2	C7—N3—C8	118.24 (17)
N3—C7—H7A	109.5	C9—N4—C10	122.0 (2)
N3—C7—H7B	109.5	C9—N4—C11	120.33 (19)
H7A—C7—H7B	109.5	C10—N4—C11	117.48 (19)
N3—C7—H7C	109.5	C6—O1—Ni	126.39 (13)
H7A—C7—H7C	109.5	Ni—Cl1—Niⁱⁱ	93.628 (17)
H7B—C7—H7C	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NA···Cl2^iv	0.89 (2)	2.60 (2)	3.4869 (16)	176.4 (1)
N2—H2NB···O2^v	0.84 (2)	2.11 (2)	2.925 (2)	173.3 (1)

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

Experimental details

Crystal data
Chemical formula	[NiCl₂(C₅H₆N₂)(C₃H₇NO)]·C₃H₇NO
M_r	369.92
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.3684 (2), 15.0571 (3), 10.0976 (2)
β (°)	103.832 (2)
V (Å³)	1530.70 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.38 × 0.30 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.628, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6140, 2748, 2333
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.058, 1.04
No. of reflections	2748
No. of parameters	193
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.34

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NA···Cl2ⁱ	0.89 (2)	2.60 (2)	3.4869 (16)	176.4 (1)
N2—H2NB···O2ⁱⁱ	0.84 (2)	2.11 (2)	2.925 (2)	173.3 (1)

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

Acknowledgements

We are grateful to the Taoyuan Innovation Institute of Technology for supporting this work.

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