cis-Dichlorido[2-(3,5-dimethyl-1H-pyrazol-1-yl-κN2)ethanamine-κN]palladium(II) dichloro­methane monosolvate

Obuah, C.; Darkwa, J.; Muller, A.

doi:10.1107/S1600536812032308

metal-organic compounds

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Volume 68| Part 8| August 2012| Page m1103

https://doi.org/10.1107/S1600536812032308

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cis-Dichlorido[2-(3,5-dimethyl-1H-pyrazol-1-yl-κN²)ethanamine-κN]palladium(II) dichloromethane monosolvate

Collins Obuah,^a James Darkwa ^a and Alfred Muller ^a ^*

^aDepartment of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
^*Correspondence e-mail: mullera@uj.ac.za

(Received 4 July 2012; accepted 16 July 2012; online 21 July 2012)

In the title compound, [PdCl₂(C₇H₁₃N₃)]·CH₂Cl₂, the 2-(3,5-dimethyl-1H-pyrazol-1-yl)ethanamine ligand chelates the Pd^II atom via two N atoms forming a six-membered ring resulting in a distorted square-planar metal coordination environment, highlighted by N—Pd—Cl angles of 172.63 (8) and 174.98 (9)°. In addition to N—H⋯Cl hydrogen bonds creating infinite chains along [001], several C—H⋯Cl interactions are observed in the crystal structure.

Related literature

For the synthesis and catalytic applications of Schiff base complexes, see: Connor et al. (2003 ); Wang et al. (1998 ). For catalytic hydrolysis of free and bound imines, see: Nolan & Hay (1974 ); Satchell & Satchell (1979 ); Hay (1987 ); Bähr & Thämlitz (1955 ); Bähr & Döge (1957 ).

Experimental

Crystal data

[PdCl₂(C₇H₁₃N₃)]·CH₂Cl₂
M_r = 401.43
Monoclinic, P 2₁ /c
a = 11.9415 (11) Å
b = 11.432 (1) Å
c = 10.5901 (10) Å
β = 97.087 (2)°
V = 1434.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.02 mm⁻¹
T = 100 K
0.31 × 0.27 × 0.26 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.574, T_max = 0.622
18522 measured reflections
3582 independent reflections
3373 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.11
3582 reflections
155 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.28 e Å⁻³
Δρ_min = −1.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯Cl1ⁱ	0.87 (2)	2.51 (4)	3.230 (3)	141 (5)
N3—H3B⋯Cl2ⁱ	0.87 (2)	2.66 (5)	3.297 (3)	131 (5)
N3—H3A⋯Cl3	0.86 (2)	2.79 (2)	3.631 (3)	169 (4)
C4—H4A⋯Cl2ⁱⁱ	0.99	2.76	3.720 (3)	163
C4—H4A⋯Cl2ⁱⁱ	0.99	2.76	3.720 (3)	163
C7—H7A⋯Cl1	0.98	2.74	3.455 (4)	130
C8—H8A⋯Cl2	0.99	2.71	3.428 (4)	130
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2011 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812032308/bt5968sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812032308/bt5968Isup2.hkl

checkCIF report

Comment top

Schiff base complexes have been synthesized and used in a number of catalytic reactions (Connor et al., 2003; Wang et al., 1998). Their popularity stems from their ease of synthesis, their ability to stabilize metals in different oxidation states and the ability to modify both the electronic and steric properties of the ligand. However, several reports of metal ions catalyzing the hydrolysis of free imines (Nolan & Hay, 1974; Satchell & Satchell, 1979; Hay, 1987) and bound imines (Bähr & Thämlitz, 1955; Bähr & Döge, 1957) have been reported. In an attempt to prepare [{2-(3,5-di-methylpyrazol-1-yl)-ethyl-(ferrocenylmethyl-methylene)-imine}PdCl₂] as olefin transformation catalyst, we found the title compound 1 formed as a result of hydrolysis of the imine by the Pd(II) starting material.

The title compound 1 (Figure 1) cis-[(3,5-di-methylpyrazol-1-yl-ethylamine)PdCl₂] crystallizes in the P2₁/c (Z=4) space group with an accompanying CH₂Cl₂ solvate. Chelation of the pyrazolylamine to the metal coordination environment is distorted, highlighted by the dihedral angle of 7.75 (8)° between the Cl1—Pd–Cl2 and N1—Pd—N3 planes. The N—Pd—Cl angles of 172.63 (8) and 174.98 (9)° are further evidence of this distortion. Pd—Cl bond distances of 2.3070 (7) and 2.3004 (7) differ marginally, possibly due to the different electronic capabilities of the donor atoms of the pyrazolylamine.

Several N/C···Cl interactions are observed (see table 1), creating infinite one-dimensional chains along the [001] direction as shown in Figure 2.

Related literature top

For the synthesis and catalytic applications of Schiff base complexes, see: Connor et al. (2003); Wang et al. (1998). For catalytic hydrolysis of free and bound imines, see: Nolan & Hay (1974); Satchell & Satchell (1979); Hay (1987); Bähr & Thämlitz (1955); Bähr & Döge (1957).

Experimental top

A CH₂Cl₂ solution (20 ml) of 2-(3,5-di-methylpyrazol-1-yl)-ethyl-(ferrocenylmethyl-methylene)-imine (0.10 g, 0.28 mmol) was added to [PdCl₂(CNMe)₂] (0.07 g, 0.28 mmol) in CH₂Cl₂ (10 ml) while stirring. The resulting mixture was stirred for 18 h at 25 °C after, which hexane was added to precipitate an orange solid. The solid was filtered, washed three times with hexane and dried in air.

Light yellow single crystals were grown by slow evaporation at room temperature in CH₂Cl₂. Yield = 0.07 g, 80%.

¹H NMR (CDCl₃): δ 2.37 (s, 3H, CH₃); 2.58 (s, 3H, CH₃); 2.36 (s, 3H, CH₃); 4.37 (s, 4H, CH₂); 5.84 (s, 1H, pz). IR (Diamond ATR, cm^-1): 3435 ν(NH)

Structure description top

Several N/C···Cl interactions are observed (see table 1), creating infinite one-dimensional chains along the [001] direction as shown in Figure 2.

For the synthesis and catalytic applications of Schiff base complexes, see: Connor et al. (2003); Wang et al. (1998). For catalytic hydrolysis of free and bound imines, see: Nolan & Hay (1974); Satchell & Satchell (1979); Hay (1987); Bähr & Thämlitz (1955); Bähr & Döge (1957).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of (I). Displacement ellipsoids are drawn at a 50% probability level.
	Fig. 2. Packing diagram of (I) showing the infinite one-dimensional chains created along the [001] direction.

cis-Dichlorido[2-(3,5-dimethyl-1H-pyrazol-1-yl- κN²)ethanamine-κN]palladium(II) dichloromethane monosolvate top

Crystal data top

[PdCl₂(C₇H₁₃N₃)]·CH₂Cl₂	F(000) = 792
M_r = 401.43	D_x = 1.859 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9923 reflections
a = 11.9415 (11) Å	θ = 2.5–28.4°
b = 11.432 (1) Å	µ = 2.02 mm⁻¹
c = 10.5901 (10) Å	T = 100 K
β = 97.087 (2)°	Cube, orange
V = 1434.7 (2) Å³	0.31 × 0.27 × 0.26 mm
Z = 4

Data collection top

Bruker X8 APEXII 4K KappaCCD diffractometer	3582 independent reflections
Graphite monochromator	3373 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm^-1	R_int = 0.021
ω & φ scans	θ_max = 28.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
T_min = 0.574, T_max = 0.622	k = −15→14
18522 measured reflections	l = −14→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0378P)² + 4.6095P] where P = (F_o² + 2F_c²)/3
3582 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 2.28 e Å⁻³
2 restraints	Δρ_min = −1.12 e Å⁻³

Crystal data top

[PdCl₂(C₇H₁₃N₃)]·CH₂Cl₂	V = 1434.7 (2) Å³
M_r = 401.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9415 (11) Å	µ = 2.02 mm⁻¹
b = 11.432 (1) Å	T = 100 K
c = 10.5901 (10) Å	0.31 × 0.27 × 0.26 mm
β = 97.087 (2)°

Data collection top

Bruker X8 APEXII 4K KappaCCD diffractometer	3582 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3373 reflections with I > 2σ(I)
T_min = 0.574, T_max = 0.622	R_int = 0.021
18522 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	2 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 2.28 e Å⁻³
3582 reflections	Δρ_min = −1.12 e Å⁻³
155 parameters

Special details top

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 10 s/frame. A total of 1491 frames were collected with a frame width of 0.5° covering up to θ = 28.40° with 99.5% completeness accomplished.

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
Pd1	0.560565 (18)	0.158108 (19)	0.080787 (19)	0.01469 (8)
Cl1	0.64115 (6)	0.16169 (7)	−0.10627 (7)	0.02358 (16)
Cl2	0.38953 (6)	0.22298 (6)	−0.01819 (6)	0.01848 (14)
Cl3	0.18032 (8)	0.10624 (10)	0.19406 (9)	0.0377 (2)
Cl4	0.07255 (8)	0.14275 (8)	−0.06665 (10)	0.0362 (2)
N1	0.7084 (2)	0.1182 (2)	0.1833 (2)	0.0174 (5)
N2	0.7127 (2)	0.0281 (2)	0.2683 (2)	0.0187 (5)
N3	0.4849 (2)	0.1402 (3)	0.2426 (2)	0.0211 (5)
C1	0.8094 (3)	0.1697 (3)	0.1996 (3)	0.0190 (6)
C2	0.8790 (3)	0.1109 (3)	0.2939 (3)	0.0241 (6)
H2	0.9555	0.1286	0.3233	0.029*
C3	0.8152 (3)	0.0221 (3)	0.3364 (3)	0.0243 (6)
C4	0.6096 (3)	−0.0357 (3)	0.2823 (3)	0.0209 (6)
H4A	0.6271	−0.1015	0.3424	0.025*
H4B	0.5782	−0.0688	0.199	0.025*
C5	0.5224 (3)	0.0435 (3)	0.3313 (3)	0.0242 (6)
H5A	0.456	−0.004	0.3463	0.029*
H5B	0.5548	0.0771	0.414	0.029*
C6	0.8449 (4)	−0.0700 (4)	0.4360 (4)	0.0400 (9)
H6A	0.803	−0.0556	0.5084	0.06*
H6B	0.9261	−0.0671	0.4647	0.06*
H6C	0.8251	−0.1473	0.4	0.06*
C7	0.8348 (3)	0.2783 (3)	0.1295 (3)	0.0270 (7)
H7A	0.822	0.2636	0.0377	0.041*
H7B	0.9137	0.3008	0.1539	0.041*
H7C	0.7852	0.3417	0.1511	0.041*
C8	0.1640 (3)	0.0524 (3)	0.0354 (4)	0.0302 (7)
H8A	0.2387	0.0491	0.0041	0.036*
H8B	0.133	−0.0279	0.0341	0.036*
H3A	0.4137 (17)	0.137 (4)	0.220 (4)	0.033 (12)*
H3B	0.492 (5)	0.204 (3)	0.287 (5)	0.067 (19)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.01967 (12)	0.01323 (12)	0.01177 (11)	−0.00021 (7)	0.00431 (8)	0.00061 (7)
Cl1	0.0239 (3)	0.0321 (4)	0.0162 (3)	0.0084 (3)	0.0083 (3)	0.0089 (3)
Cl2	0.0209 (3)	0.0198 (3)	0.0152 (3)	0.0011 (2)	0.0042 (2)	−0.0005 (2)
Cl3	0.0388 (5)	0.0452 (6)	0.0314 (4)	0.0025 (4)	0.0136 (4)	0.0040 (4)
Cl4	0.0366 (5)	0.0254 (4)	0.0442 (5)	0.0005 (3)	−0.0050 (4)	−0.0017 (4)
N1	0.0235 (12)	0.0153 (12)	0.0141 (11)	−0.0003 (9)	0.0049 (9)	0.0015 (9)
N2	0.0282 (13)	0.0138 (12)	0.0140 (11)	−0.0024 (9)	0.0015 (9)	0.0015 (9)
N3	0.0184 (12)	0.0343 (16)	0.0110 (11)	0.0007 (10)	0.0033 (9)	0.0009 (10)
C1	0.0225 (14)	0.0177 (14)	0.0172 (13)	−0.0002 (11)	0.0042 (10)	0.0007 (11)
C2	0.0259 (15)	0.0223 (16)	0.0229 (14)	−0.0006 (12)	−0.0020 (11)	0.0023 (12)
C3	0.0333 (16)	0.0184 (15)	0.0195 (14)	0.0001 (12)	−0.0031 (12)	0.0015 (11)
C4	0.0334 (16)	0.0126 (13)	0.0174 (13)	−0.0052 (11)	0.0060 (11)	−0.0001 (10)
C5	0.0375 (17)	0.0193 (15)	0.0179 (13)	−0.0045 (13)	0.0110 (12)	0.0002 (11)
C6	0.049 (2)	0.031 (2)	0.036 (2)	−0.0079 (17)	−0.0139 (17)	0.0140 (16)
C7	0.0290 (16)	0.0234 (17)	0.0293 (16)	−0.0047 (13)	0.0062 (12)	0.0081 (13)
C8	0.0289 (16)	0.0224 (16)	0.0400 (19)	0.0001 (13)	0.0066 (14)	0.0009 (14)

Geometric parameters (Å, º) top

Pd1—N1	2.007 (3)	C2—H2	0.95
Pd1—N3	2.044 (3)	C3—C6	1.501 (5)
Pd1—Cl2	2.3004 (7)	C4—C5	1.519 (4)
Pd1—Cl1	2.3070 (7)	C4—H4A	0.99
Cl3—C8	1.777 (4)	C4—H4B	0.99
Cl4—C8	1.770 (4)	C5—H5A	0.99
N1—C1	1.335 (4)	C5—H5B	0.99
N1—N2	1.365 (3)	C6—H6A	0.98
N2—C3	1.344 (4)	C6—H6B	0.98
N2—C4	1.454 (4)	C6—H6C	0.98
N3—C5	1.484 (4)	C7—H7A	0.98
N3—H3A	0.855 (19)	C7—H7B	0.98
N3—H3B	0.87 (2)	C7—H7C	0.98
C1—C2	1.391 (4)	C8—H8A	0.99
C1—C7	1.496 (4)	C8—H8B	0.99
C2—C3	1.378 (5)

N1—Pd1—N3	88.52 (10)	C5—C4—H4A	109.4
N1—Pd1—Cl2	172.63 (8)	N2—C4—H4B	109.4
N3—Pd1—Cl2	87.40 (8)	C5—C4—H4B	109.4
N1—Pd1—Cl1	92.08 (7)	H4A—C4—H4B	108
N3—Pd1—Cl1	174.98 (9)	N3—C5—C4	113.2 (2)
Cl2—Pd1—Cl1	92.52 (3)	N3—C5—H5A	108.9
C1—N1—N2	106.7 (2)	C4—C5—H5A	108.9
C1—N1—Pd1	133.7 (2)	N3—C5—H5B	108.9
N2—N1—Pd1	119.16 (19)	C4—C5—H5B	108.9
C3—N2—N1	110.5 (3)	H5A—C5—H5B	107.7
C3—N2—C4	130.2 (3)	C3—C6—H6A	109.5
N1—N2—C4	118.9 (2)	C3—C6—H6B	109.5
C5—N3—Pd1	118.4 (2)	H6A—C6—H6B	109.5
C5—N3—H3A	111 (3)	C3—C6—H6C	109.5
Pd1—N3—H3A	107 (3)	H6A—C6—H6C	109.5
C5—N3—H3B	106 (4)	H6B—C6—H6C	109.5
Pd1—N3—H3B	110 (4)	C1—C7—H7A	109.5
H3A—N3—H3B	103 (5)	C1—C7—H7B	109.5
N1—C1—C2	109.3 (3)	H7A—C7—H7B	109.5
N1—C1—C7	122.5 (3)	C1—C7—H7C	109.5
C2—C1—C7	128.1 (3)	H7A—C7—H7C	109.5
C3—C2—C1	106.6 (3)	H7B—C7—H7C	109.5
C3—C2—H2	126.7	Cl4—C8—Cl3	111.3 (2)
C1—C2—H2	126.7	Cl4—C8—H8A	109.4
N2—C3—C2	106.9 (3)	Cl3—C8—H8A	109.4
N2—C3—C6	122.3 (3)	Cl4—C8—H8B	109.4
C2—C3—C6	130.8 (3)	Cl3—C8—H8B	109.4
N2—C4—C5	111.1 (3)	H8A—C8—H8B	108
N2—C4—H4A	109.4

N3—Pd1—N1—C1	−127.5 (3)	Pd1—N1—C1—C7	−3.4 (5)
Cl1—Pd1—N1—C1	57.5 (3)	N1—C1—C2—C3	−1.0 (4)
N3—Pd1—N1—N2	43.7 (2)	C7—C1—C2—C3	175.0 (3)
Cl1—Pd1—N1—N2	−131.3 (2)	N1—N2—C3—C2	−0.1 (4)
C1—N1—N2—C3	−0.5 (3)	C4—N2—C3—C2	−172.6 (3)
Pd1—N1—N2—C3	−173.9 (2)	N1—N2—C3—C6	−179.1 (3)
C1—N1—N2—C4	173.0 (3)	C4—N2—C3—C6	8.4 (5)
Pd1—N1—N2—C4	−0.4 (3)	C1—C2—C3—N2	0.7 (4)
N1—Pd1—N3—C5	−39.8 (2)	C1—C2—C3—C6	179.5 (4)
Cl2—Pd1—N3—C5	146.4 (2)	C3—N2—C4—C5	109.0 (4)
N2—N1—C1—C2	1.0 (3)	N1—N2—C4—C5	−63.0 (3)
Pd1—N1—C1—C2	172.9 (2)	Pd1—N3—C5—C4	−3.9 (4)
N2—N1—C1—C7	−175.4 (3)	N2—C4—C5—N3	63.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···Cl1ⁱ	0.87 (2)	2.51 (4)	3.230 (3)	141 (5)
N3—H3B···Cl2ⁱ	0.87 (2)	2.66 (5)	3.297 (3)	131 (5)
N3—H3A···Cl3	0.86 (2)	2.79 (2)	3.631 (3)	169 (4)
C4—H4A···Cl2ⁱⁱ	0.99	2.76	3.720 (3)	163
C4—H4A···Cl2ⁱⁱ	0.99	2.76	3.720 (3)	163
C7—H7A···Cl1	0.98	2.74	3.455 (4)	130
C8—H8A···Cl2	0.99	2.71	3.428 (4)	130

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

Experimental details

Crystal data
Chemical formula	[PdCl₂(C₇H₁₃N₃)]·CH₂Cl₂
M_r	401.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.9415 (11), 11.432 (1), 10.5901 (10)
β (°)	97.087 (2)
V (Å³)	1434.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.02
Crystal size (mm)	0.31 × 0.27 × 0.26

Data collection
Diffractometer	Bruker X8 APEXII 4K KappaCCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.574, 0.622
No. of measured, independent and observed [I > 2σ(I)] reflections	18522, 3582, 3373
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.085, 1.11
No. of reflections	3582
No. of parameters	155
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	2.28, −1.12

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2008), SAINT and XPREP (Bruker, 2008), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···Cl1ⁱ	0.87 (2)	2.51 (4)	3.230 (3)	141 (5)
N3—H3B···Cl2ⁱ	0.87 (2)	2.66 (5)	3.297 (3)	131 (5)
N3—H3A···Cl3	0.855 (19)	2.79 (2)	3.631 (3)	169 (4)
C4—H4A···Cl2ⁱⁱ	0.99	2.76	3.720 (3)	163.3
C4—H4A···Cl2ⁱⁱ	0.99	2.76	3.720 (3)	163.3
C7—H7A···Cl1	0.98	2.74	3.455 (4)	129.7
C8—H8A···Cl2	0.99	2.71	3.428 (4)	129.5

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

Acknowledgements

Research funds of the University of Johannesburg and the Research Center for Synthesis and Catalysis are gratefully acknowledged. Mrs Z. Phasha is thanked for the data collection.

References

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