Chlorido­bis­(ethane-1,2-di­amine-κ2N,N′)(3-methyl­pyridine-κN)cobalt(III) dichloride monohydrate

Hemanathan, K.; Mahalakshmi, C.M.; Anbalagan, K.; Raja, R.; Murugesan, K.S.

doi:10.1107/S2414314618010258

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 7| July 2018| x181025

https://doi.org/10.1107/S2414314618010258

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Chloridobis(ethane-1,2-diamine-κ²N,N′)(3-methylpyridine-κN)cobalt(III) dichloride monohydrate

K. Hemanathan,^a C. Maharaja Mahalakshmi,^b K. Anbalagan,^c R. Raja ^a and K. Sakthi Murugesan ^a ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^bDepartment of Chemistry, Chellammal Womens College, Guindy, Chennai 600 032, India, and ^cDepartment of Chemistry, Pondicherry University, Pondicherry 605 014, India
^*Correspondence e-mail: ksakthimurugesan2492@gmail.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 21 June 2018; accepted 16 July 2018; online 24 July 2018)

In the title hydrated salt, [CoCl(C₆H₇N)(C₂H₈N₂)₂]Cl₂·H₂O, the Co^III ion exhibits a distorted octahedral coordination envirnoment defined by four N atoms of two ethane-1,2-diamine ligands, another N atom of the pyridine ligand and a Cl⁻ ligand. The pyridine N atom and the Cl⁻ ligand are in cis positions relative to each other. The crystal packing is dominated by intermolecular N—H⋯Cl, O—H⋯Cl and O—H⋯H hydrogen-bonding interactions involving the amino groups of the complex cation, the lattice water molecule and the non-coordinating Cl⁻ anions. Weak C—H⋯Cl interactions consolidate the three-dimensional hydrogen-bonded network structure.

Keywords: crystal structure; ethane-1,2-diamine ligand; 3-methylpyridine ligand; cobalt(III); hydrogen bonding.

CCDC reference: 794322

Structure description

Cobalt is an essential and integral component of vitamin B₁₂. Hence it is found physiologically in most tissues. Complexes of cobalt are useful for nutritional supplementation to provide this element in a form that effectively increases the bioavailability, for instance, vitamin B₁₂ by microorganisms present in the gut. Cobalt(III) complexes with ethane-1,2-diamine or with mixed ligands exhibit antitumor, antibacterial, antimicrobial, radiosenzitation and cytotoxicity activities (Sayed et al., 1992 ; Teicher et al., 1990 ; Arslan et al., 2009 ; Delehanty et al., 2008 ). In addition, cobalt(III) complexes are known for electron-transfer and ligand-substitution reactions. In this context, we have synthesized another cobalt(III) complex with mixed ligands, [CoCl(C₆H₇N)(C₂H₈N₂)₂]Cl₂·H₂O, and report here its crystal structure.

The structural entities of the title compound are shown in Fig. 1. The Co^III cation is octahedrally surrounded by four N atoms of two ethane-1,2-diamine ligands, a pyridine N atom and a Cl⁻ ligand, whereby the pyridine N atom and the Cl⁻ ligand are cis to each other. The Co—N and Co—Cl bond lengths are typical for trivalent cobalt and comparable with related complexes comprising of N- and Cl-donating ligands (Anbalagan et al., 2009 ; Ramesh et al., 2008 ; Ravichandran et al., 2009 ). The least-squares planes of the two ethane-1,2-diamine ligands make a dihedral angle of 78.0 (2)°. Puckering parameters for the Co1/N1/C9/C8/N2 and Co1/N3/C7/C6/N4 rings are: q₂ = 0.439 (3) Å, φ = 86.4 (3)° and q₂ = 0.422 (3)°, φ = 82.2 (3)°, respectively. According to Nardelli (1983 ), ring asymmetry parameters from out-of-plane displacements are Δ₂(Co1) = 3.6 (2)°for the first metalla ring and Δ₂(Co1) = 7.4 (2)° for the second ring.

Figure 1
The molecular entities in the title structure with displacement ellipsoids at the 30% probability level.

The complex cation, chloride anions and lattice water molecule are linked into a three-dimensional network by intermolecular N—H⋯Cl, O—H⋯Cl and O—H⋯O hydrogen-bonding interactions, supplemented by weaker C—H⋯Cl interactions (Table 1 and Fig. 2). This involves an R₂²(4) ring motif between two adjacent water molecules (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl3	0.93	2.66	3.585 (3)	174
C8—H8A⋯Cl3ⁱ	0.97	2.90	3.395 (3)	113
C9—H9B⋯Cl3ⁱⁱ	0.97	2.95	3.440 (3)	113
N1—H1A⋯Cl3ⁱⁱ	0.85 (2)	2.41 (2)	3.194 (2)	153 (2)
N1—H1B⋯Cl4ⁱⁱⁱ	0.86 (2)	2.48 (2)	3.292 (2)	157 (2)
N2—H2A⋯Cl4	0.85 (2)	2.57 (2)	3.370 (2)	158 (2)
N2—H2B⋯Cl3	0.86 (2)	2.70 (2)	3.383 (2)	137 (2)
N2—H2B⋯Cl3ⁱ	0.86 (2)	2.86 (2)	3.514 (3)	135 (2)
N3—H3A⋯Cl4	0.85 (2)	2.36 (2)	3.191 (2)	168 (3)
N3—H3B⋯Cl4ⁱⁱⁱ	0.86 (2)	2.67 (2)	3.406 (2)	144 (2)
N4—H4A⋯Cl3	0.84 (2)	2.38 (2)	3.178 (3)	160 (2)
N4—H4B⋯Cl2^iv	0.85 (2)	2.64 (2)	3.310 (2)	137 (2)
O1—H1C⋯Cl4	0.87 (2)	2.28 (2)	3.120 (3)	162 (4)
O1—H1D⋯O1^v	0.85 (2)	2.45 (1)	2.940 (7)	118 (1)
Symmetry codes: (i) -x+1, -y, -z+2; (ii) x-1, y, z; (iii) -x, -y, -z+1; (iv) -x+1, -y+1, -z+2; (v) -x, -y-1, -z+1.

Figure 2
A view along the a axis of the title compound, emphasizing the molecular packing. N—H⋯Cl, O—H⋯O, O—H⋯Cl and C—H⋯Cl hydrogen bonds are shown as dashed lines (see Table 1

for numerical details).

Figure 3
A partial of the crystal packing of the title compound, showing an R₂²(4) motif formed via an inversion-related pair of O—H⋯O hydrogen bonds (dashed lines).

Synthesis and crystallization

The complex was synthesized using dichloridobis(ethane-1,2-diamine)cobalt(III) chloride (Bailar & Clapp, 1945 ) as a precursor. trans-[Co^III(en)₂Cl₂]Cl (2 g) was suspended in 3–4 drops of deionized water. Then 3-methylpyridine (3 ml) was added dropwise for 20 min, resulting in a colour change from dull green to violet–red. The final mixture was stirred for 30 min and continued for another 30 min until no further change was observed. The mixture was allowed to stand overnight. Finally, the obtained solid was washed 3–4 times with ethanol and dissolved in 5–10 ml of deionized water that had been pre-heated to 343 K. The title cobalt(III) complex was recrystallized by cooling this solution to which a few drops of conc. HCl were added. The resulting crystals were filtered, washed with ethanol and dried under vacuum.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	[CoCl(C₆H₇N)(C₂H₈N₂)₂]Cl₂·H₂O
M_r	396.63
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	7.6771 (4), 10.8911 (5), 11.6132 (7)
α, β, γ (°)	113.439 (5), 99.872 (5), 102.384 (4)
V (Å³)	833.67 (8)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.51
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
No. of measured, independent and observed [I > 2σ(I)] reflections	5316, 2929, 2456
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.087, 1.09
No. of reflections	2929
No. of parameters	219
No. of restraints	16
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.37
Computer programs: APEX2 and SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 794322

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618010258/wm4082sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618010258/wm4082Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Chloridobis(ethane-1,2-diamine-κ²N,N')(3-methylpyridine-κN)cobalt(III) dichloride monohydrate top

Crystal data top

[CoCl(C₆H₇N)(C₂H₈N₂)₂]Cl₂·H₂O	Z = 2
M_r = 396.63	F(000) = 412
Triclinic, P1	D_x = 1.580 Mg m⁻³
a = 7.6771 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8911 (5) Å	Cell parameters from 2456 reflections
c = 11.6132 (7) Å	θ = 2.8–25.0°
α = 113.439 (5)°	µ = 1.51 mm⁻¹
β = 99.872 (5)°	T = 293 K
γ = 102.384 (4)°	Block, violet-red
V = 833.67 (8) Å³	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2456 reflections with I > 2σ(I)
ω and φ scans	R_int = 0.025
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 25.0°, θ_min = 2.8°
	h = −8→9
5316 measured reflections	k = −12→12
2929 independent reflections	l = −13→13

Refinement top

Refinement on F²	16 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0515P)²] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
2929 reflections	Δρ_max = 0.61 e Å⁻³
219 parameters	Δρ_min = −0.37 e Å⁻³

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.

Refinement. H atoms of water molecules and amino groups were located from difference maps and refined with restraints on their bond lengths [(N,O)—H = 0.85 Å]).

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

	x	y	z	U_iso*/U_eq
C1	0.3844 (3)	0.2624 (3)	1.1036 (3)	0.0201 (6)
H1	0.4616	0.2135	1.0660	0.024*
C2	0.4109 (4)	0.3106 (3)	1.2368 (3)	0.0234 (6)
C3	0.2932 (4)	0.3807 (3)	1.2909 (3)	0.0262 (7)
H3	0.3058	0.4145	1.3801	0.031*
C4	0.1575 (4)	0.4004 (3)	1.2127 (3)	0.0258 (7)
H4	0.0770	0.4468	1.2485	0.031*
C5	0.1409 (3)	0.3511 (3)	1.0809 (3)	0.0218 (6)
H5	0.0495	0.3658	1.0287	0.026*
C6	0.5567 (4)	0.2506 (3)	0.7483 (3)	0.0234 (6)
H6A	0.5676	0.1565	0.7171	0.028*
H6B	0.6754	0.3155	0.7618	0.028*
C7	0.4074 (4)	0.2550 (3)	0.6496 (3)	0.0249 (6)
H7A	0.4120	0.3515	0.6712	0.030*
H7B	0.4222	0.2111	0.5626	0.030*
C8	0.0579 (3)	−0.0546 (3)	0.7964 (3)	0.0205 (6)
H8A	0.0380	−0.0344	0.8815	0.025*
H8B	0.0465	−0.1537	0.7514	0.025*
C9	−0.0815 (3)	−0.0193 (3)	0.7177 (3)	0.0193 (6)
H9A	−0.0744	−0.0526	0.6283	0.023*
H9B	−0.2067	−0.0630	0.7162	0.023*
C10	0.5621 (4)	0.2841 (3)	1.3149 (3)	0.0361 (8)
H10A	0.6269	0.2340	1.2583	0.054*
H10B	0.6479	0.3724	1.3820	0.054*
H10C	0.5085	0.2290	1.3546	0.054*
N1	−0.0337 (3)	0.1366 (2)	0.7830 (2)	0.0169 (5)
N2	0.2452 (3)	0.0339 (2)	0.8119 (2)	0.0157 (5)
N3	0.2283 (3)	0.1755 (2)	0.6559 (2)	0.0174 (5)
N4	0.5063 (3)	0.2910 (2)	0.8731 (2)	0.0176 (5)
N5	0.2547 (3)	0.2816 (2)	1.0253 (2)	0.0162 (5)
Cl2	0.20805 (9)	0.43180 (7)	0.85882 (7)	0.02175 (17)
Cl3	0.69806 (8)	0.09570 (7)	0.95580 (7)	0.02316 (18)
Cl4	0.21383 (9)	−0.14314 (7)	0.49221 (6)	0.02355 (18)
Co1	0.23612 (4)	0.22144 (3)	0.83760 (3)	0.01406 (13)
O1	−0.0839 (4)	−0.4040 (3)	0.4680 (4)	0.0880 (12)
H1C	0.017 (5)	−0.341 (4)	0.477 (4)	0.106*
H1D	−0.061 (6)	−0.415 (3)	0.536 (2)	0.106*
H1A	−0.087 (3)	0.157 (3)	0.8438 (19)	0.021 (8)*
H1B	−0.088 (3)	0.159 (3)	0.727 (2)	0.011 (7)*
H2A	0.270 (3)	−0.007 (2)	0.7402 (16)	0.005 (6)*
H2B	0.324 (3)	0.033 (3)	0.8730 (18)	0.024 (8)*
H3A	0.207 (4)	0.0875 (19)	0.613 (3)	0.035 (9)*
H3B	0.149 (3)	0.201 (3)	0.617 (3)	0.035 (9)*
H4A	0.559 (3)	0.255 (2)	0.914 (2)	0.021 (8)*
H4B	0.545 (3)	0.3800 (17)	0.918 (3)	0.021 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0157 (13)	0.0211 (14)	0.0193 (15)	0.0033 (11)	0.0038 (11)	0.0069 (12)
C2	0.0220 (15)	0.0205 (14)	0.0203 (15)	−0.0022 (12)	−0.0005 (12)	0.0091 (12)
C3	0.0342 (17)	0.0233 (15)	0.0155 (15)	0.0023 (13)	0.0085 (12)	0.0063 (13)
C4	0.0300 (16)	0.0222 (14)	0.0237 (16)	0.0076 (13)	0.0134 (13)	0.0070 (13)
C5	0.0168 (14)	0.0233 (14)	0.0251 (16)	0.0066 (12)	0.0066 (12)	0.0102 (13)
C6	0.0155 (14)	0.0317 (15)	0.0251 (16)	0.0046 (12)	0.0096 (12)	0.0146 (13)
C7	0.0222 (15)	0.0297 (15)	0.0232 (16)	0.0029 (12)	0.0084 (12)	0.0141 (13)
C8	0.0200 (14)	0.0208 (14)	0.0223 (15)	0.0044 (11)	0.0079 (11)	0.0117 (12)
C9	0.0135 (13)	0.0218 (14)	0.0184 (15)	0.0000 (11)	0.0037 (11)	0.0082 (12)
C10	0.0334 (17)	0.0446 (19)	0.0266 (18)	0.0097 (15)	0.0021 (14)	0.0162 (15)
N1	0.0144 (11)	0.0241 (12)	0.0141 (12)	0.0067 (10)	0.0034 (10)	0.0104 (11)
N2	0.0129 (11)	0.0204 (11)	0.0107 (12)	0.0032 (9)	0.0008 (9)	0.0061 (10)
N3	0.0155 (12)	0.0191 (12)	0.0180 (13)	0.0036 (10)	0.0030 (10)	0.0105 (11)
N4	0.0140 (11)	0.0182 (12)	0.0175 (13)	0.0036 (10)	0.0009 (9)	0.0071 (11)
N5	0.0143 (11)	0.0172 (11)	0.0145 (12)	0.0021 (9)	0.0033 (9)	0.0065 (10)
Cl2	0.0220 (3)	0.0182 (3)	0.0227 (4)	0.0065 (3)	0.0029 (3)	0.0082 (3)
Cl3	0.0162 (3)	0.0339 (4)	0.0271 (4)	0.0100 (3)	0.0087 (3)	0.0191 (3)
Cl4	0.0265 (4)	0.0270 (4)	0.0179 (4)	0.0121 (3)	0.0043 (3)	0.0099 (3)
Co1	0.0103 (2)	0.0168 (2)	0.0132 (2)	0.00278 (14)	0.00175 (14)	0.00627 (16)
O1	0.069 (2)	0.067 (2)	0.156 (4)	0.0194 (17)	0.063 (2)	0.066 (2)

Geometric parameters (Å, º) top

C1—N5	1.339 (4)	C9—N1	1.485 (3)
C1—C2	1.381 (4)	C9—H9A	0.9700
C1—H1	0.9300	C9—H9B	0.9700
C2—C3	1.380 (4)	C10—H10A	0.9600
C2—C10	1.499 (4)	C10—H10B	0.9600
C3—C4	1.373 (4)	C10—H10C	0.9600
C3—H3	0.9300	N1—Co1	1.952 (2)
C4—C5	1.377 (4)	N1—H1A	0.852 (15)
C4—H4	0.9300	N1—H1B	0.859 (16)
C5—N5	1.357 (3)	N2—Co1	1.962 (2)
C5—H5	0.9300	N2—H2A	0.852 (15)
C6—N4	1.484 (3)	N2—H2B	0.858 (16)
C6—C7	1.499 (4)	N3—Co1	1.952 (2)
C6—H6A	0.9700	N3—H3A	0.847 (17)
C6—H6B	0.9700	N3—H3B	0.855 (17)
C7—N3	1.490 (3)	N4—Co1	1.957 (2)
C7—H7A	0.9700	N4—H4A	0.836 (16)
C7—H7B	0.9700	N4—H4B	0.848 (16)
C8—N2	1.485 (3)	N5—Co1	1.980 (2)
C8—C9	1.500 (4)	Cl2—Co1	2.2664 (7)
C8—H8A	0.9700	O1—H1C	0.874 (18)
C8—H8B	0.9700	O1—H1D	0.845 (19)

N5—C1—C2	124.2 (2)	H10B—C10—H10C	109.5
N5—C1—H1	117.9	C9—N1—Co1	109.48 (15)
C2—C1—H1	117.9	C9—N1—H1A	106.5 (18)
C3—C2—C1	117.3 (3)	Co1—N1—H1A	116.0 (18)
C3—C2—C10	123.2 (3)	C9—N1—H1B	106.8 (18)
C1—C2—C10	119.5 (3)	Co1—N1—H1B	111.6 (16)
C4—C3—C2	119.7 (3)	H1A—N1—H1B	106.0 (19)
C4—C3—H3	120.1	C8—N2—Co1	109.53 (16)
C2—C3—H3	120.1	C8—N2—H2A	105.7 (16)
C3—C4—C5	119.7 (3)	Co1—N2—H2A	109.5 (16)
C3—C4—H4	120.1	C8—N2—H2B	108.4 (19)
C5—C4—H4	120.1	Co1—N2—H2B	115.4 (19)
N5—C5—C4	121.6 (3)	H2A—N2—H2B	107.8 (19)
N5—C5—H5	119.2	C7—N3—Co1	110.22 (16)
C4—C5—H5	119.2	C7—N3—H3A	111 (2)
N4—C6—C7	108.4 (2)	Co1—N3—H3A	109 (2)
N4—C6—H6A	110.0	C7—N3—H3B	102 (2)
C7—C6—H6A	110.0	Co1—N3—H3B	115 (2)
N4—C6—H6B	110.0	H3A—N3—H3B	109 (2)
C7—C6—H6B	110.0	C6—N4—Co1	110.18 (16)
H6A—C6—H6B	108.4	C6—N4—H4A	107.2 (19)
N3—C7—C6	105.6 (2)	Co1—N4—H4A	110.4 (19)
N3—C7—H7A	110.6	C6—N4—H4B	110.0 (19)
C6—C7—H7A	110.6	Co1—N4—H4B	109.6 (17)
N3—C7—H7B	110.6	H4A—N4—H4B	109 (2)
C6—C7—H7B	110.6	C1—N5—C5	117.4 (2)
H7A—C7—H7B	108.8	C1—N5—Co1	121.98 (17)
N2—C8—C9	107.0 (2)	C5—N5—Co1	120.51 (19)
N2—C8—H8A	110.3	N1—Co1—N3	89.50 (9)
C9—C8—H8A	110.3	N1—Co1—N4	173.58 (9)
N2—C8—H8B	110.3	N3—Co1—N4	85.02 (9)
C9—C8—H8B	110.3	N1—Co1—N2	85.27 (9)
H8A—C8—H8B	108.6	N3—Co1—N2	91.85 (10)
N1—C9—C8	106.3 (2)	N4—Co1—N2	91.55 (10)
N1—C9—H9A	110.5	N1—Co1—N5	93.08 (9)
C8—C9—H9A	110.5	N3—Co1—N5	176.00 (9)
N1—C9—H9B	110.5	N4—Co1—N5	92.58 (9)
C8—C9—H9B	110.5	N2—Co1—N5	91.41 (9)
H9A—C9—H9B	108.7	N1—Co1—Cl2	91.55 (7)
C2—C10—H10A	109.5	N3—Co1—Cl2	86.76 (7)
C2—C10—H10B	109.5	N4—Co1—Cl2	91.49 (8)
H10A—C10—H10B	109.5	N2—Co1—Cl2	176.54 (7)
C2—C10—H10C	109.5	N5—Co1—Cl2	90.11 (7)
H10A—C10—H10C	109.5	H1C—O1—H1D	105 (3)

N5—C1—C2—C3	1.2 (4)	C8—C9—N1—Co1	41.2 (2)
N5—C1—C2—C10	−179.4 (3)	C9—C8—N2—Co1	38.1 (2)
C1—C2—C3—C4	−0.3 (4)	C6—C7—N3—Co1	40.9 (2)
C10—C2—C3—C4	−179.7 (3)	C7—C6—N4—Co1	34.9 (3)
C2—C3—C4—C5	−0.6 (4)	C2—C1—N5—C5	−1.0 (4)
C3—C4—C5—N5	0.7 (4)	C2—C1—N5—Co1	175.57 (19)
N4—C6—C7—N3	−48.6 (3)	C4—C5—N5—C1	0.0 (4)
N2—C8—C9—N1	−51.2 (3)	C4—C5—N5—Co1	−176.61 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl3	0.93	2.66	3.585 (3)	174
C8—H8A···Cl3ⁱ	0.97	2.90	3.395 (3)	113
C9—H9B···Cl3ⁱⁱ	0.97	2.95	3.440 (3)	113
N1—H1A···Cl3ⁱⁱ	0.85 (2)	2.41 (2)	3.194 (2)	153 (2)
N1—H1B···Cl4ⁱⁱⁱ	0.86 (2)	2.48 (2)	3.292 (2)	157 (2)
N2—H2A···Cl4	0.85 (2)	2.57 (2)	3.370 (2)	158 (2)
N2—H2B···Cl3	0.86 (2)	2.70 (2)	3.383 (2)	137 (2)
N2—H2B···Cl3ⁱ	0.86 (2)	2.86 (2)	3.514 (3)	135 (2)
N3—H3A···Cl4	0.85 (2)	2.36 (2)	3.191 (2)	168 (3)
N3—H3B···Cl4ⁱⁱⁱ	0.86 (2)	2.67 (2)	3.406 (2)	144 (2)
N4—H4A···Cl3	0.84 (2)	2.38 (2)	3.178 (3)	160 (2)
N4—H4B···Cl2^iv	0.85 (2)	2.64 (2)	3.310 (2)	137 (2)
O1—H1C···Cl4	0.87 (2)	2.28 (2)	3.120 (3)	162 (4)
O1—H1D···O1^v	0.85 (2)	2.45 (1)	2.940 (7)	118 (1)

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

Funding information

KA records his sincere thanks to the Council of Scientific and Industrial Research- HRDG, New Delhi, Department of Science and Technology – SERC, Government of India, New Delhi for financial support through major research projects.

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