Tri­carbonyl­chlorido­(6′,7′-di­hydro-5′H-spiro­[cyclo­hexane-1,6′-dipyrido[3,2-d:2′,3′-f][1,3]diazepine]-κ2N1,N11)rhenium(I)

Clegg, O.R.; Harding, L.P.; Miller, J.W.; Rice, C.R.

doi:10.1107/S1600536813024288

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page m527

doi:10.1107/S1600536813024288

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Tricarbonylchlorido(6′,7′-dihydro-5′H-spiro[cyclohexane-1,6′-dipyrido[3,2-d:2′,3′-f][1,3]diazepine]-κ²N¹,N¹¹)rhenium(I)

Oliver R. Clegg,^a Lindsay P. Harding,^a ^* John W. Miller ^a and Craig R. Rice ^a

^aDepartment of Chemical & Biological Sciences, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, England
^*Correspondence e-mail: l.p.harding@hud.ac.uk

(Received 7 August 2013; accepted 30 August 2013; online 4 September 2013)

In the title compound, [ReCl(C₁₆H₁₈N₄)(CO)₃], the Re^I ion is coordinated in a distorted octahedral geometry by one Cl atom, two N atoms of the bidentate ligand and three carbonyl groups. The cyclohexane group is orientated in a transoid fashion with respect to the chloride ligand. In the crystal, N—H⋯Cl hydrogen bonds link complex molecules, forming a two-dimensional network parallel to (100).

Related literature

For a review of the photophysical properties of Re–polypyridyl complexes, see: Coleman et al. (2008 ). For the synthesis of [Re(3,3′-diamino-2,2′-bipyridine)(CO)₃Cl] and for the preparation of oxo-steroid derivatives of [Re(3,3′-diamino-2,2′-bipyridine)(CO)₃Cl], see: Bullock et al. (2012 ). For the reaction of [Re(3,3′-diamino-2,2′-bipyridine)(CO)₃Cl] with ketones, see: Clayton et al. (2008 ). For the structure of the cyclopentane analogue of the title compound, see: Clegg et al. (2013 ).

Experimental

Crystal data

[ReCl(C₁₆H₁₈N₄)(CO)₃]
M_r = 572.02
Monoclinic, P 2₁ /c
a = 12.6794 (6) Å
b = 11.9040 (6) Å
c = 12.7732 (6) Å
β = 97.066 (1)°
V = 1913.29 (16) Å³
Z = 4
Mo Kα radiation
μ = 6.52 mm⁻¹
T = 150 K
0.10 × 0.10 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.562, T_max = 0.828
22579 measured reflections
5590 independent reflections
4543 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.051
S = 1.04
5590 reflections
259 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.08 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Cl1ⁱ	0.89 (3)	2.64 (2)	3.417 (3)	146 (3)
N4—H4⋯Cl1ⁱⁱ	0.89 (3)	2.46 (3)	3.334 (3)	171 (3)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813024288/lh5645sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813024288/lh5645Isup2.hkl

checkCIF report

Comment top

The title complex was prepared as part of a larger study into conjugation of [Re(3,3'-diamino-2,2'-bipyridine)(CO)₃Cl] with oxo-steroids to form luminescent derivatives (Bullock et al. 2012). These steroids contain a cyclohexyl ring (ring A) with a ketone group in the 3-position; therefore, cyclohexanone was used as a model compound to examine the potential reactivity of such steroids with the rhenium complex.

Single-crystal X-ray analysis of the title complex gave the structure shown in Fig. 1. The rhenium centre adopts a distorted octahedral geometry which is coordinated by two nitrogen atoms from a 3,3'-diamino-2,2'-bipyridyl ligand and two carbonyl ligands in the equatorial sites and by a carbonyl ligand and a chloride ion in the axial sites. The cyclohexyl ring adopts a chair conformation and is orientated in a trans-oid fashion relative to the chloride ion on the rhenium centre. In the crystal, N—H···Cl hydrogen bonds (Table 1 & Fig. 2) link complex molecules to form a two-dimensional network parallel (100).

A similar compound has been prepared using cyclopentanone instead of cyclohexanone. The title compound compound is essentially isostructural with that compound (Clegg et al. 2013).

Related literature top

For a review of the photophysical properties of Re–polypyridyl complexes, see: Coleman et al. (2008). For the synthesis of [Re(3,3'-diamino-2,2'-bipyridine)(CO)₃Cl] and for the preparation of oxo-steroid derivatives of [Re(3,3'-diamino-2,2'-bipyridine)(CO)₃Cl], see: Bullock et al. (2012). For the reaction of [Re(3,3'-diamino-2,2'-bipyridine)(CO)₃Cl] with ketones, see: Clayton et al. (2008). For the structure of the cyclopentane analogue of the title compound, see: Clegg et al. (2013).

Experimental top

To a solution of [Re(3,3'-diamino-2,2'-bipyridine)(CO)₃Cl] in dichloromethane was added cyclohexanone (10 µL, ca. 2 eq.) and a few grains of camphorsulfonic acid. The solution was stirred at room temperature for 2 h. The resulting precipitate was filtered in vacuo, washed with dichloromethane and dried, giving the product as a yellow solid. Crystals suitable for X-ray analysis were prepared by slow evaporation of an acetonitrile solution of the complex.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids shown at the 50% probability level.

Tricarbonylchlorido(6',7'-dihydro-5'H-spiro[cyclohexane-1,6'-dipyrido[3,2-d:2',3'-f][1,3]diazepine]-κ²N¹,N¹¹)rhenium(I) top

Crystal data top

[ReCl(C₁₆H₁₈N₄)(CO)₃]	F(000) = 1104
M_r = 572.02	D_x = 1.986 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6672 reflections
a = 12.6794 (6) Å	θ = 2.4–30.2°
b = 11.9040 (6) Å	µ = 6.52 mm⁻¹
c = 12.7732 (6) Å	T = 150 K
β = 97.066 (1)°	Block, yellow
V = 1913.29 (16) Å³	0.10 × 0.10 × 0.03 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5590 independent reflections
Radiation source: fine-focus sealed tube	4543 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
T_min = 0.562, T_max = 0.828	k = −16→16
22579 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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.051	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0164P)² + 1.9168P] where P = (F_o² + 2F_c²)/3
5590 reflections	(Δ/σ)_max = 0.002
259 parameters	Δρ_max = 1.08 e Å⁻³
2 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

[ReCl(C₁₆H₁₈N₄)(CO)₃]	V = 1913.29 (16) Å³
M_r = 572.02	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6794 (6) Å	µ = 6.52 mm⁻¹
b = 11.9040 (6) Å	T = 150 K
c = 12.7732 (6) Å	0.10 × 0.10 × 0.03 mm
β = 97.066 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5590 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4543 reflections with I > 2σ(I)
T_min = 0.562, T_max = 0.828	R_int = 0.039
22579 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	2 restraints
wR(F²) = 0.051	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 1.08 e Å⁻³
5590 reflections	Δρ_min = −0.74 e Å⁻³
259 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
Re1	0.209524 (11)	0.453951 (10)	0.250974 (9)	0.01842 (4)
Cl1	0.33970 (7)	0.60427 (7)	0.21693 (7)	0.02644 (18)
N1	0.3302 (2)	0.4016 (2)	0.37600 (19)	0.0185 (5)
N2	0.1863 (2)	0.5567 (2)	0.38525 (19)	0.0199 (5)
N3	0.3158 (2)	0.6174 (2)	0.6529 (2)	0.0215 (6)
N4	0.4188 (2)	0.4503 (3)	0.6590 (2)	0.0310 (7)
O1	0.0385 (2)	0.5624 (2)	0.09147 (18)	0.0306 (6)
O2	0.2669 (3)	0.3038 (2)	0.0706 (2)	0.0477 (8)
O3	0.0489 (2)	0.2781 (2)	0.3017 (2)	0.0387 (7)
C1	0.1030 (3)	0.5197 (3)	0.1503 (2)	0.0226 (7)
C2	0.2461 (3)	0.3609 (3)	0.1381 (3)	0.0286 (8)
C3	0.1102 (3)	0.3443 (3)	0.2834 (2)	0.0255 (7)
C4	0.3337 (2)	0.4527 (3)	0.4731 (2)	0.0189 (6)
C5	0.4093 (3)	0.4144 (3)	0.5566 (2)	0.0209 (7)
C6	0.4833 (3)	0.3319 (3)	0.5338 (3)	0.0227 (7)
H6	0.5368	0.3080	0.5878	0.027*
C7	0.4792 (3)	0.2859 (3)	0.4357 (3)	0.0255 (7)
H7	0.5293	0.2307	0.4206	0.031*
C8	0.4001 (3)	0.3219 (3)	0.3585 (3)	0.0229 (7)
H8	0.3954	0.2887	0.2905	0.027*
C9	0.2552 (2)	0.5444 (3)	0.4760 (2)	0.0175 (6)
C10	0.2467 (3)	0.6191 (3)	0.5607 (2)	0.0195 (6)
C11	0.1681 (3)	0.7017 (3)	0.5486 (3)	0.0268 (8)
H11	0.1617	0.7523	0.6050	0.032*
C12	0.1001 (3)	0.7113 (3)	0.4572 (3)	0.0309 (8)
H12	0.0465	0.7675	0.4495	0.037*
C13	0.1117 (3)	0.6367 (3)	0.3764 (3)	0.0273 (8)
H13	0.0651	0.6425	0.3125	0.033*
C14	0.3416 (3)	0.5122 (3)	0.7096 (2)	0.0234 (7)
C15	0.2419 (3)	0.4398 (3)	0.7144 (3)	0.0296 (8)
H15A	0.2073	0.4253	0.6419	0.036*
H15B	0.2628	0.3665	0.7474	0.036*
C16	0.1653 (4)	0.4967 (4)	0.7762 (3)	0.0432 (10)
H16A	0.1025	0.4480	0.7792	0.052*
H16B	0.1411	0.5678	0.7410	0.052*
C17	0.2176 (4)	0.5216 (4)	0.8886 (3)	0.0514 (13)
H17A	0.1662	0.5610	0.9281	0.062*
H17B	0.2374	0.4500	0.9254	0.062*
C18	0.3166 (4)	0.5941 (4)	0.8870 (3)	0.0401 (10)
H18A	0.2956	0.6691	0.8580	0.048*
H18B	0.3516	0.6044	0.9600	0.048*
C19	0.3935 (3)	0.5414 (3)	0.8214 (3)	0.0335 (8)
H19A	0.4228	0.4720	0.8567	0.040*
H19B	0.4534	0.5937	0.8165	0.040*
H3	0.305 (3)	0.678 (2)	0.691 (3)	0.040*
H4	0.479 (2)	0.433 (3)	0.699 (3)	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Re1	0.01938 (6)	0.01328 (6)	0.02209 (6)	0.00027 (6)	0.00050 (4)	−0.00139 (5)
Cl1	0.0213 (4)	0.0212 (4)	0.0355 (4)	−0.0005 (3)	−0.0016 (3)	0.0099 (3)
N1	0.0202 (14)	0.0109 (13)	0.0243 (12)	−0.0002 (11)	0.0020 (11)	0.0016 (10)
N2	0.0188 (13)	0.0153 (13)	0.0243 (12)	0.0019 (12)	−0.0032 (10)	−0.0022 (10)
N3	0.0240 (15)	0.0139 (14)	0.0251 (13)	−0.0009 (12)	−0.0037 (12)	−0.0009 (10)
N4	0.0241 (16)	0.0336 (17)	0.0322 (14)	0.0131 (15)	−0.0091 (12)	−0.0073 (14)
O1	0.0313 (14)	0.0297 (14)	0.0285 (12)	0.0044 (12)	−0.0052 (11)	−0.0035 (10)
O2	0.073 (2)	0.0393 (17)	0.0327 (14)	0.0243 (16)	0.0140 (15)	−0.0042 (12)
O3	0.0384 (17)	0.0295 (15)	0.0479 (15)	−0.0119 (13)	0.0033 (13)	−0.0002 (12)
C1	0.0260 (18)	0.0169 (17)	0.0252 (15)	−0.0050 (14)	0.0042 (14)	−0.0069 (12)
C2	0.035 (2)	0.0219 (18)	0.0287 (16)	0.0060 (17)	0.0044 (15)	0.0051 (14)
C3	0.029 (2)	0.0202 (18)	0.0258 (15)	0.0002 (15)	−0.0018 (14)	−0.0042 (13)
C4	0.0164 (14)	0.0124 (14)	0.0272 (14)	−0.0039 (14)	−0.0005 (12)	−0.0013 (12)
C5	0.0183 (16)	0.0157 (15)	0.0281 (15)	−0.0021 (13)	0.0002 (13)	−0.0006 (12)
C6	0.0153 (16)	0.0156 (16)	0.0362 (17)	0.0022 (13)	−0.0008 (14)	0.0016 (12)
C7	0.0216 (18)	0.0154 (16)	0.0402 (18)	0.0034 (14)	0.0072 (15)	0.0018 (13)
C8	0.0234 (18)	0.0146 (16)	0.0308 (16)	0.0033 (14)	0.0045 (14)	−0.0009 (12)
C9	0.0186 (15)	0.0122 (14)	0.0209 (12)	−0.0008 (14)	−0.0013 (11)	0.0017 (12)
C10	0.0196 (16)	0.0116 (15)	0.0262 (14)	−0.0005 (13)	−0.0024 (13)	0.0003 (11)
C11	0.029 (2)	0.0181 (17)	0.0319 (16)	0.0064 (15)	−0.0016 (15)	−0.0077 (13)
C12	0.033 (2)	0.0236 (19)	0.0348 (18)	0.0124 (17)	−0.0033 (16)	−0.0046 (14)
C13	0.0263 (19)	0.0232 (18)	0.0300 (16)	0.0091 (16)	−0.0061 (14)	−0.0033 (14)
C14	0.0254 (18)	0.0201 (17)	0.0227 (14)	0.0045 (14)	−0.0052 (13)	−0.0018 (12)
C15	0.040 (2)	0.0168 (18)	0.0308 (16)	−0.0015 (16)	−0.0001 (16)	0.0025 (13)
C16	0.043 (3)	0.039 (2)	0.049 (2)	−0.009 (2)	0.012 (2)	−0.0029 (19)
C17	0.071 (4)	0.045 (3)	0.042 (2)	−0.001 (2)	0.022 (2)	−0.0035 (19)
C18	0.048 (3)	0.040 (2)	0.0311 (19)	−0.001 (2)	−0.0006 (18)	−0.0039 (16)
C19	0.037 (2)	0.033 (2)	0.0267 (15)	0.0077 (19)	−0.0094 (15)	−0.0033 (15)

Geometric parameters (Å, º) top

Re1—C3	1.895 (4)	C7—H7	0.9500
Re1—C1	1.914 (3)	C8—H8	0.9500
Re1—C2	1.919 (4)	C9—C10	1.414 (4)
Re1—N2	2.156 (3)	C10—C11	1.395 (5)
Re1—N1	2.163 (3)	C11—C12	1.368 (5)
Re1—Cl1	2.5083 (9)	C11—H11	0.9500
N1—C8	1.335 (4)	C12—C13	1.383 (5)
N1—C4	1.377 (4)	C12—H12	0.9500
N2—C13	1.338 (4)	C13—H13	0.9500
N2—C9	1.370 (4)	C14—C19	1.537 (4)
N3—C10	1.378 (4)	C14—C15	1.538 (5)
N3—C14	1.464 (4)	C15—C16	1.488 (6)
N3—H3	0.895 (18)	C15—H15A	0.9900
N4—C5	1.367 (4)	C15—H15B	0.9900
N4—C14	1.440 (5)	C16—C17	1.534 (6)
N4—H4	0.895 (19)	C16—H16A	0.9900
O1—C1	1.158 (4)	C16—H16B	0.9900
O2—C2	1.154 (4)	C17—C18	1.526 (6)
O3—C3	1.151 (4)	C17—H17A	0.9900
C4—C5	1.418 (4)	C17—H17B	0.9900
C4—C9	1.482 (4)	C18—C19	1.500 (5)
C5—C6	1.413 (5)	C18—H18A	0.9900
C6—C7	1.362 (5)	C18—H18B	0.9900
C6—H6	0.9500	C19—H19A	0.9900
C7—C8	1.386 (5)	C19—H19B	0.9900

C3—Re1—C1	89.74 (14)	N3—C10—C11	118.4 (3)
C3—Re1—C2	89.72 (15)	N3—C10—C9	122.9 (3)
C1—Re1—C2	86.96 (14)	C11—C10—C9	118.6 (3)
C3—Re1—N2	93.30 (12)	C12—C11—C10	121.3 (3)
C1—Re1—N2	98.55 (11)	C12—C11—H11	119.4
C2—Re1—N2	173.72 (13)	C10—C11—H11	119.4
C3—Re1—N1	93.94 (12)	C11—C12—C13	118.0 (3)
C1—Re1—N1	172.11 (11)	C11—C12—H12	121.0
C2—Re1—N1	100.02 (13)	C13—C12—H12	121.0
N2—Re1—N1	74.30 (10)	N2—C13—C12	122.2 (3)
C3—Re1—Cl1	176.99 (10)	N2—C13—H13	118.9
C1—Re1—Cl1	90.96 (10)	C12—C13—H13	118.9
C2—Re1—Cl1	93.23 (12)	N4—C14—N3	109.8 (3)
N2—Re1—Cl1	83.70 (8)	N4—C14—C19	107.2 (3)
N1—Re1—Cl1	85.01 (7)	N3—C14—C19	108.1 (3)
C8—N1—C4	121.0 (3)	N4—C14—C15	109.8 (3)
C8—N1—Re1	120.3 (2)	N3—C14—C15	111.4 (3)
C4—N1—Re1	118.6 (2)	C19—C14—C15	110.5 (3)
C13—N2—C9	121.2 (3)	C16—C15—C14	111.1 (3)
C13—N2—Re1	120.1 (2)	C16—C15—H15A	109.4
C9—N2—Re1	118.5 (2)	C14—C15—H15A	109.4
C10—N3—C14	121.0 (3)	C16—C15—H15B	109.4
C10—N3—H3	110 (3)	C14—C15—H15B	109.4
C14—N3—H3	117 (3)	H15A—C15—H15B	108.0
C5—N4—C14	127.2 (3)	C15—C16—C17	110.5 (4)
C5—N4—H4	116 (3)	C15—C16—H16A	109.6
C14—N4—H4	116 (3)	C17—C16—H16A	109.6
O1—C1—Re1	177.8 (3)	C15—C16—H16B	109.6
O2—C2—Re1	178.9 (4)	C17—C16—H16B	109.6
O3—C3—Re1	179.0 (3)	H16A—C16—H16B	108.1
N1—C4—C5	118.6 (3)	C18—C17—C16	111.0 (3)
N1—C4—C9	113.6 (3)	C18—C17—H17A	109.4
C5—C4—C9	127.8 (3)	C16—C17—H17A	109.4
N4—C5—C6	115.6 (3)	C18—C17—H17B	109.4
N4—C5—C4	126.2 (3)	C16—C17—H17B	109.4
C6—C5—C4	118.2 (3)	H17A—C17—H17B	108.0
C7—C6—C5	121.2 (3)	C19—C18—C17	111.3 (3)
C7—C6—H6	119.4	C19—C18—H18A	109.4
C5—C6—H6	119.4	C17—C18—H18A	109.4
C6—C7—C8	118.2 (3)	C19—C18—H18B	109.4
C6—C7—H7	120.9	C17—C18—H18B	109.4
C8—C7—H7	120.9	H18A—C18—H18B	108.0
N1—C8—C7	122.5 (3)	C18—C19—C14	112.4 (3)
N1—C8—H8	118.7	C18—C19—H19A	109.1
C7—C8—H8	118.7	C14—C19—H19A	109.1
N2—C9—C10	118.7 (3)	C18—C19—H19B	109.1
N2—C9—C4	114.7 (3)	C14—C19—H19B	109.1
C10—C9—C4	126.6 (3)	H19A—C19—H19B	107.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cl1ⁱ	0.89 (3)	2.64 (2)	3.417 (3)	146 (3)
N4—H4···Cl1ⁱⁱ	0.89 (3)	2.46 (3)	3.334 (3)	171 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cl1ⁱ	0.89 (3)	2.64 (2)	3.417 (3)	146 (3)
N4—H4···Cl1ⁱⁱ	0.89 (3)	2.46 (3)	3.334 (3)	171 (3)

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

Acknowledgements

The authors wish to thank the University of Huddersfield for financial support.

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