2,2-Dibenzyl­hydrazin-1-ium chloride

Tayamon, S.; Ravoof, T.B.S.A.; Tahir, M.I.M.; Crouse, K.A.; Tiekink, E.R.T.

doi:10.1107/S1600536813003966

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o382

doi:10.1107/S1600536813003966

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2,2-Dibenzylhydrazin-1-ium chloride

Shahedeh Tayamon,^a Thahira Begum S. A. Ravoof,^a Mohamed Ibrahim Mohamed Tahir,^a Karen A. Crouse ^a ‡ and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 4 February 2013; accepted 8 February 2013; online 16 February 2013)

In the title salt, C₁₄H₁₇N₂⁺·Cl⁻, the central N atom is pyramidal (sum of bond angles = 330.9°) and there is a near orthogonal relationship between the benzene rings [dihedral angle = 89.95 (10)°]. The crystal packing features N—H⋯Cl hydrogen bonds, which lead to a supramolecular undulating ribbon along the a axis comprising edge-shared eight-membered {⋯HNH⋯Cl}₂ synthons. The chains are connected into layers in the ab plane by C—H⋯π interactions.

Related literature

For background to the synthesis of S-substituted dithiocarbazates and their metal complexes, see: Ravoof et al. (2010 ); Tayamon et al. (2012 ). For the synthesis, see: Tarafder et al. (2000 ). For the structure of the diphenyl analogue of the cation, see: Stender et al. (2003 ).

Experimental

Crystal data

C₁₄H₁₇N₂⁺·Cl⁻
M_r = 248.75
Triclinic, $[P \overline 1]$
a = 5.6155 (4) Å
b = 9.9804 (7) Å
c = 11.7302 (9) Å
α = 79.532 (6)°
β = 78.508 (6)°
γ = 83.550 (6)°
V = 631.54 (8) Å³
Z = 2
Cu Kα radiation
μ = 2.49 mm⁻¹
T = 100 K
0.14 × 0.09 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.72, T_max = 0.95
6961 measured reflections
2407 independent reflections
2076 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.129
S = 1.07
2407 reflections
166 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯Cl1	0.94 (3)	2.30 (3)	3.2130 (18)	163 (2)
N2—H2N⋯Cl1ⁱ	0.97 (2)	2.21 (2)	3.1287 (19)	158 (2)
N2—H3N⋯Cl1ⁱⁱ	0.93 (3)	2.20 (3)	3.1235 (18)	172 (2)
C8—H8A⋯Cg1ⁱⁱⁱ	0.99	2.64	3.542 (2)	152
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813003966/hb7036sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813003966/hb7036Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813003966/hb7036Isup3.cml

checkCIF report

Comment top

In continuation of efforts to explore the structure-activity relationships of new S-substituted dithiocarbazates and their metal complexes (Ravoof et al., 2010; Tayamon et al., 2012), the title salt (I) was obtained during an attempt to prepare the benzylhydrazine analogue of S-benzyldithiocarbazate.

The asymmetric unit of salt (I) comprises a 2,2-dibenzylhydrazinium cation and a chloride anion, Fig. 1. The sum of the angles about the N1 atom approximates 331° confirming its pyramidal nature. The dihedral angle between the phenyl rings is 89.95 (10)°, thereby displaying an orthogonal relationship. Hydrazinium cations are comparatively rare in the crystallographic literature with the most closely related structure being that of the diphenyl analogue, isolated as its [Au(CN)₂^-] salt monohydrate (Stender et al., 2003). The N—N distance in this structure of 1.453 (5) Å is indistinguishable from that in (I) of 1.453 (2) Å.

The crystal packing is dominated by N—H···Cl hydrogen bonds, Table 1. Each ammonium—H atom forms a hydrogen atom with a chloride to generate an undulating ribbon along the a axis comprising edge-shared eight-membered {···HNH···Cl}₂ synthons, Fig. 2. These are connected into layers in the ab plane by C—H···π interactions, Fig. 3 and Table 2. Layers stack along the c axis with no specific interactions between them.

Related literature top

For background to the synthesis of S-substituted dithiocarbazates and their metal complexes, see: Ravoof et al. (2010); Tayamon et al. (2012). For the synthesis, see: Tarafder et al. (2000). For the structure of the diphenyl analogue of the cation, see: Stender et al. (2003).

Experimental top

The title compound was isolated as a side-product during the synthesis of a benzylhydrazine analogue of S-benzyldithiocarbazate using a procedure adapted from Tarafder et al. (2000). Potassium hydroxide (0.02 mol, 1.12 g) and benzylhydrazine (0.02 mol, 3.9 g) were each completely dissolved in chloroform (20 ml). The benzylhydrazine solution was added to the cooled mixture of potassium hydroxide. The combined solution was kept in an ice-salt bath while carbon disulfide (0.02 mol, 1.52 g) was added with constant stirring over one hour. Benzylchloride (0.02 mol, 2.3 ml) was added drop-wise to the above mixture with vigorous stirring. The initial precipitate was removed by filtration and then diethyl ether was added to the solution. A precipitate (0.63 g) was filtered from the solution after one day. Pale-yellow crystals of the title salt (M.pt > 583 K) were harvested from the filtrate on the second day (0.30 g).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of salt (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the undulating supramolecular chain in (I) mediated by N—H···Cl hydrogen bonds (blue dashed lines) along the a axis.
	Fig. 3. A view of the crystal packing in projection down the a axis. The N—H···Cl and C—H···π interactions are shown as blue and purple dashed lines, respectively.

2,2-Dibenzylhydrazin-1-ium chloride top

Crystal data top

C₁₄H₁₇N₂⁺·Cl⁻	Z = 2
M_r = 248.75	F(000) = 264
Triclinic, P1	D_x = 1.308 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 5.6155 (4) Å	Cell parameters from 3230 reflections
b = 9.9804 (7) Å	θ = 4–71°
c = 11.7302 (9) Å	µ = 2.49 mm⁻¹
α = 79.532 (6)°	T = 100 K
β = 78.508 (6)°	Plate, colourless
γ = 83.550 (6)°	0.14 × 0.09 × 0.02 mm
V = 631.54 (8) Å³

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2407 independent reflections
Radiation source: fine-focus sealed tube	2076 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 16.1952 pixels mm^-1	θ_max = 71.5°, θ_min = 3.9°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→11
T_min = 0.72, T_max = 0.95	l = −14→14
6961 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.079P)² + 0.1383P] where P = (F_o² + 2F_c²)/3
2407 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₇N₂⁺·Cl⁻	γ = 83.550 (6)°
M_r = 248.75	V = 631.54 (8) Å³
Triclinic, P1	Z = 2
a = 5.6155 (4) Å	Cu Kα radiation
b = 9.9804 (7) Å	µ = 2.49 mm⁻¹
c = 11.7302 (9) Å	T = 100 K
α = 79.532 (6)°	0.14 × 0.09 × 0.02 mm
β = 78.508 (6)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2407 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2076 reflections with I > 2σ(I)
T_min = 0.72, T_max = 0.95	R_int = 0.034
6961 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.45 e Å⁻³
2407 reflections	Δρ_min = −0.24 e Å⁻³
166 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.84514 (8)	0.01710 (5)	0.33994 (4)	0.02664 (19)
N1	0.2435 (3)	0.28342 (17)	0.37150 (14)	0.0250 (4)
N2	0.2870 (3)	0.13600 (18)	0.40100 (16)	0.0248 (4)
H1n	0.444 (5)	0.104 (3)	0.367 (2)	0.033 (6)*
H2n	0.264 (4)	0.109 (3)	0.486 (2)	0.034 (6)*
H3n	0.167 (5)	0.095 (3)	0.379 (2)	0.041 (7)*
C1	0.2203 (4)	0.3190 (2)	0.24543 (18)	0.0279 (5)
H1A	0.1843	0.4191	0.2271	0.033*
H1B	0.0782	0.2754	0.2346	0.033*
C2	0.4393 (4)	0.2781 (2)	0.15639 (17)	0.0250 (4)
C3	0.6219 (4)	0.3662 (2)	0.10779 (19)	0.0309 (5)
H3	0.6066	0.4551	0.1280	0.037*
C4	0.8266 (4)	0.3253 (2)	0.02986 (19)	0.0340 (5)
H4	0.9500	0.3863	−0.0029	0.041*
C5	0.8508 (4)	0.1958 (2)	0.00005 (19)	0.0313 (5)
H5	0.9908	0.1676	−0.0529	0.038*
C6	0.6703 (4)	0.1077 (2)	0.04771 (18)	0.0301 (5)
H6	0.6871	0.0185	0.0279	0.036*
C7	0.4638 (4)	0.1489 (2)	0.12462 (18)	0.0281 (5)
H7	0.3389	0.0884	0.1556	0.034*
C8	0.4435 (4)	0.3486 (2)	0.40018 (18)	0.0269 (5)
H8A	0.4279	0.4481	0.3709	0.032*
H8B	0.6021	0.3107	0.3601	0.032*
C9	0.4366 (4)	0.3245 (2)	0.53131 (18)	0.0244 (4)
C10	0.6359 (4)	0.2601 (2)	0.57891 (19)	0.0282 (5)
H10	0.7779	0.2302	0.5281	0.034*
C11	0.6301 (4)	0.2389 (2)	0.70000 (19)	0.0285 (5)
H11	0.7673	0.1944	0.7313	0.034*
C12	0.4247 (4)	0.2827 (2)	0.77478 (18)	0.0269 (5)
H12	0.4207	0.2693	0.8574	0.032*
C13	0.2239 (4)	0.3465 (2)	0.72795 (18)	0.0275 (5)
H13	0.0817	0.3759	0.7790	0.033*
C14	0.2303 (4)	0.3675 (2)	0.60783 (18)	0.0259 (4)
H14	0.0925	0.4117	0.5769	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0242 (3)	0.0312 (3)	0.0251 (3)	−0.00283 (19)	−0.00452 (19)	−0.0057 (2)
N1	0.0277 (9)	0.0256 (9)	0.0217 (9)	−0.0021 (7)	−0.0038 (7)	−0.0047 (7)
N2	0.0237 (10)	0.0277 (10)	0.0233 (9)	−0.0037 (7)	−0.0040 (7)	−0.0041 (7)
C1	0.0296 (11)	0.0293 (11)	0.0236 (10)	0.0006 (9)	−0.0047 (8)	−0.0032 (8)
C2	0.0274 (11)	0.0294 (11)	0.0186 (9)	−0.0006 (8)	−0.0065 (8)	−0.0035 (8)
C3	0.0404 (13)	0.0289 (11)	0.0240 (10)	−0.0048 (9)	−0.0060 (9)	−0.0048 (9)
C4	0.0356 (12)	0.0416 (14)	0.0242 (11)	−0.0113 (10)	−0.0013 (9)	−0.0035 (9)
C5	0.0276 (11)	0.0420 (13)	0.0237 (10)	0.0012 (9)	−0.0037 (8)	−0.0072 (9)
C6	0.0356 (12)	0.0308 (12)	0.0247 (10)	0.0016 (9)	−0.0072 (9)	−0.0073 (9)
C7	0.0299 (11)	0.0313 (11)	0.0236 (10)	−0.0043 (9)	−0.0058 (8)	−0.0037 (9)
C8	0.0278 (11)	0.0293 (11)	0.0234 (10)	−0.0066 (8)	−0.0010 (8)	−0.0054 (8)
C9	0.0249 (10)	0.0247 (10)	0.0243 (10)	−0.0071 (8)	−0.0016 (8)	−0.0057 (8)
C10	0.0245 (11)	0.0316 (11)	0.0279 (11)	−0.0033 (8)	0.0013 (8)	−0.0092 (9)
C11	0.0266 (11)	0.0279 (11)	0.0320 (11)	−0.0023 (8)	−0.0076 (9)	−0.0052 (9)
C12	0.0310 (11)	0.0291 (11)	0.0215 (10)	−0.0068 (9)	−0.0045 (8)	−0.0039 (8)
C13	0.0268 (11)	0.0280 (11)	0.0264 (11)	−0.0020 (8)	−0.0001 (8)	−0.0062 (8)
C14	0.0250 (10)	0.0256 (11)	0.0268 (10)	−0.0017 (8)	−0.0047 (8)	−0.0039 (8)

Geometric parameters (Å, º) top

N1—N2	1.453 (2)	C6—C7	1.392 (3)
N1—C8	1.481 (3)	C6—H6	0.9500
N1—C1	1.485 (3)	C7—H7	0.9500
N2—H1n	0.94 (3)	C8—C9	1.506 (3)
N2—H2n	0.97 (3)	C8—H8A	0.9900
N2—H3n	0.93 (3)	C8—H8B	0.9900
C1—C2	1.516 (3)	C9—C10	1.391 (3)
C1—H1A	0.9900	C9—C14	1.395 (3)
C1—H1B	0.9900	C10—C11	1.392 (3)
C2—C7	1.391 (3)	C10—H10	0.9500
C2—C3	1.391 (3)	C11—C12	1.383 (3)
C3—C4	1.391 (3)	C11—H11	0.9500
C3—H3	0.9500	C12—C13	1.392 (3)
C4—C5	1.385 (3)	C12—H12	0.9500
C4—H4	0.9500	C13—C14	1.380 (3)
C5—C6	1.381 (3)	C13—H13	0.9500
C5—H5	0.9500	C14—H14	0.9500

N2—N1—C8	108.71 (15)	C7—C6—H6	119.8
N2—N1—C1	108.85 (15)	C2—C7—C6	120.4 (2)
C8—N1—C1	113.32 (16)	C2—C7—H7	119.8
N1—N2—H1n	112.5 (16)	C6—C7—H7	119.8
N1—N2—H2n	110.1 (14)	N1—C8—C9	110.82 (17)
H1n—N2—H2n	109 (2)	N1—C8—H8A	109.5
N1—N2—H3n	108.9 (16)	C9—C8—H8A	109.5
H1n—N2—H3n	112 (2)	N1—C8—H8B	109.5
H2n—N2—H3n	104 (2)	C9—C8—H8B	109.5
N1—C1—C2	116.42 (16)	H8A—C8—H8B	108.1
N1—C1—H1A	108.2	C10—C9—C14	118.43 (19)
C2—C1—H1A	108.2	C10—C9—C8	120.94 (18)
N1—C1—H1B	108.2	C14—C9—C8	120.63 (18)
C2—C1—H1B	108.2	C11—C10—C9	120.91 (19)
H1A—C1—H1B	107.3	C11—C10—H10	119.5
C7—C2—C3	118.77 (19)	C9—C10—H10	119.5
C7—C2—C1	119.93 (19)	C12—C11—C10	120.03 (19)
C3—C2—C1	121.27 (18)	C12—C11—H11	120.0
C4—C3—C2	120.7 (2)	C10—C11—H11	120.0
C4—C3—H3	119.7	C11—C12—C13	119.43 (19)
C2—C3—H3	119.7	C11—C12—H12	120.3
C5—C4—C3	120.1 (2)	C13—C12—H12	120.3
C5—C4—H4	119.9	C14—C13—C12	120.40 (18)
C3—C4—H4	119.9	C14—C13—H13	119.8
C6—C5—C4	119.7 (2)	C12—C13—H13	119.8
C6—C5—H5	120.2	C13—C14—C9	120.80 (19)
C4—C5—H5	120.2	C13—C14—H14	119.6
C5—C6—C7	120.4 (2)	C9—C14—H14	119.6
C5—C6—H6	119.8

N2—N1—C1—C2	−60.2 (2)	N2—N1—C8—C9	−66.5 (2)
C8—N1—C1—C2	60.9 (2)	C1—N1—C8—C9	172.31 (16)
N1—C1—C2—C7	87.6 (2)	N1—C8—C9—C10	122.1 (2)
N1—C1—C2—C3	−90.4 (2)	N1—C8—C9—C14	−58.4 (3)
C7—C2—C3—C4	−0.7 (3)	C14—C9—C10—C11	0.0 (3)
C1—C2—C3—C4	177.35 (19)	C8—C9—C10—C11	179.45 (19)
C2—C3—C4—C5	−0.2 (3)	C9—C10—C11—C12	−0.3 (3)
C3—C4—C5—C6	0.2 (3)	C10—C11—C12—C13	0.7 (3)
C4—C5—C6—C7	0.5 (3)	C11—C12—C13—C14	−0.7 (3)
C3—C2—C7—C6	1.5 (3)	C12—C13—C14—C9	0.4 (3)
C1—C2—C7—C6	−176.61 (18)	C10—C9—C14—C13	0.0 (3)
C5—C6—C7—C2	−1.4 (3)	C8—C9—C14—C13	−179.51 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···Cl1	0.94 (3)	2.30 (3)	3.2130 (18)	163 (2)
N2—H2N···Cl1ⁱ	0.97 (2)	2.21 (2)	3.1287 (19)	158 (2)
N2—H3N···Cl1ⁱⁱ	0.93 (3)	2.20 (3)	3.1235 (18)	172 (2)
C8—H8A···Cg1ⁱⁱⁱ	0.99	2.64	3.542 (2)	152

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₇N₂⁺·Cl⁻
M_r	248.75
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.6155 (4), 9.9804 (7), 11.7302 (9)
α, β, γ (°)	79.532 (6), 78.508 (6), 83.550 (6)
V (Å³)	631.54 (8)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.49
Crystal size (mm)	0.14 × 0.09 × 0.02

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.72, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections	6961, 2407, 2076
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.129, 1.07
No. of reflections	2407
No. of parameters	166
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.24

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···Cl1	0.94 (3)	2.30 (3)	3.2130 (18)	163 (2)
N2—H2N···Cl1ⁱ	0.97 (2)	2.21 (2)	3.1287 (19)	158 (2)
N2—H3N···Cl1ⁱⁱ	0.93 (3)	2.20 (3)	3.1235 (18)	172 (2)
C8—H8A···Cg1ⁱⁱⁱ	0.99	2.64	3.542 (2)	152

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

Footnotes

‡Additional correspondence author, e-mail: crouse@pc.jaring.my.

Acknowledgements

Support for the project came from Universiti Putra Malaysia (UPM) through the purchase of the diffractometer and under their Research University Grant Scheme (RUGS No. 9174000), the Malaysian Ministry of Science, Technology and Innovation (grant No. 09–02-04–0752-EA001) and the Malaysian Fundamental Research Grant Scheme (FRGS No. 01–13-11–986FR). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

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