Bis{benzyl N′-[(1H-indol-3-yl)methyl­ene]dithio­carbazato-κ2N′,S}copper(II) N,N-dimethyl­formamide disolvate

Khaledi, H.; Mohd Ali, H.; Ng, S.W.

doi:10.1107/S1600536808043808

metal-organic compounds

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Volume 65| Part 2| February 2009| Page m139

doi:10.1107/S1600536808043808

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Bis{benzyl N′-[(1H-indol-3-yl)methylene]dithiocarbazato-κ²N′,S}copper(II) N,N-dimethylformamide disolvate

Hamid Khaledi,^a Hapipah Mohd Ali ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 23 December 2008; accepted 23 December 2008; online 8 January 2009)

In the structure of [Cu(C₁₇H₁₄N₃S₂)₂]·2C₃H₇NO, the Cu atom (site symmetry $[\overline{1}]$ ) is N,S-chelated by the two deprotonated Schiff-base anions that define a distorted square-planar geometry. An N—H⋯O hydrogen bond links the mononuclear complex to the DMF solvent molecules.

Related literature

For the Schiff base ligand, see: Khaledi et al. (2008b ). For the isostructural nickel analog, see: Khaledi et al. (2008a ).

Experimental

Crystal data

[Cu(C₁₇H₁₄N₃S₂)₂]·2C₃H₇NO
M_r = 858.60
Monoclinic, P 2₁ /c
a = 10.4461 (2) Å
b = 20.0882 (3) Å
c = 10.8333 (2) Å
β = 118.366 (1)°
V = 2000.34 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.80 mm⁻¹
T = 100 (2) K
0.25 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.825, T_max = 0.961
18600 measured reflections
4594 independent reflections
3837 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.081
S = 1.04
4594 reflections
256 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1	0.88 (2)	1.87 (2)	2.742 (2)	175 (2)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043808/tk2349sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043808/tk2349Isup2.hkl

checkCIF report

Related literature top

For the Schiff base ligand, see: Khaledi et al. (2008b). For the isostructural nickel analog, see: Khaledi et al. (2008a).

Experimental top

Benzyl (1H-indol-2-ylmethylene)hydrazinecarbodithioate (Khaledi et al., 2008b) (1 mmol, 0.33 g) was dissolved in ethanol (30 ml). To the clear solution was added an ethanol solution (10 ml) containing 1 mmol (0.09 g) of copper chloride dihydrate. The mixture was heated for an hour. The product that separated was recrystallized from DMF.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: pubCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Cu(C₁₇H₁₄N₃)^.2DMF at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Bis{benzyl N'-[(1H-indol-3-yl)methylene]dithiocarbazato- κ²N',S}copper(II) N,N-dimethylformamide disolvate top

Crystal data top

[Cu(C₁₇H₁₄N₃S₂)₂]·2C₃H₇NO	Z = 2
M_r = 858.60	F(000) = 894
Monoclinic, P2₁/c	D_x = 1.425 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.4461 (2) Å	µ = 0.80 mm⁻¹
b = 20.0882 (3) Å	T = 100 K
c = 10.8333 (2) Å	Irregular block, brown
β = 118.366 (1)°	0.25 × 0.15 × 0.05 mm
V = 2000.34 (6) Å³

Data collection top

Bruker SMART APEX diffractometer	4594 independent reflections
Radiation source: fine-focus sealed tube	3837 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.825, T_max = 0.961	k = −25→26
18600 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0382P)² + 0.7321P] where P = (F_o² + 2F_c²)/3
4594 reflections	(Δ/σ)_max = 0.001
256 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Cu(C₁₇H₁₄N₃S₂)₂]·2C₃H₇NO	V = 2000.34 (6) Å³
M_r = 858.60	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4461 (2) Å	µ = 0.80 mm⁻¹
b = 20.0882 (3) Å	T = 100 K
c = 10.8333 (2) Å	0.25 × 0.15 × 0.05 mm
β = 118.366 (1)°

Data collection top

Bruker SMART APEX diffractometer	4594 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3837 reflections with I > 2σ(I)
T_min = 0.825, T_max = 0.961	R_int = 0.035
18600 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.36 e Å⁻³
4594 reflections	Δρ_min = −0.36 e Å⁻³
256 parameters

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

	x	y	z	U_iso*/U_eq
Cu1	0.5000	0.5000	0.5000	0.01678 (8)
O1	0.8350 (2)	0.56467 (8)	−0.10421 (17)	0.0526 (5)
S1	0.51561 (5)	0.61250 (2)	0.51610 (5)	0.02414 (11)
S2	0.61468 (5)	0.70543 (2)	0.37409 (5)	0.02345 (11)
N1	0.60380 (15)	0.57545 (7)	0.32793 (14)	0.0191 (3)
N2	0.56823 (15)	0.51211 (7)	0.35752 (15)	0.0193 (3)
N3	0.72111 (17)	0.49444 (7)	0.03797 (16)	0.0234 (3)
H3N	0.756 (3)	0.5192 (11)	−0.006 (2)	0.040 (6)*
N4	0.91692 (17)	0.57480 (8)	−0.26314 (16)	0.0267 (3)
C1	0.81749 (19)	0.68443 (8)	0.27140 (19)	0.0223 (4)
C2	0.9316 (2)	0.68264 (9)	0.4074 (2)	0.0282 (4)
H2	0.9149	0.6937	0.4838	0.034*
C3	1.0699 (2)	0.66472 (10)	0.4321 (2)	0.0338 (4)
H3	1.1469	0.6628	0.5258	0.041*
C4	1.0974 (2)	0.64964 (10)	0.3226 (2)	0.0340 (5)
H4	1.1926	0.6376	0.3406	0.041*
C5	0.9852 (2)	0.65223 (10)	0.1870 (2)	0.0315 (4)
H5	1.0030	0.6423	0.1108	0.038*
C6	0.8463 (2)	0.66931 (9)	0.1618 (2)	0.0261 (4)
H6	0.7695	0.6707	0.0680	0.031*
C7	0.6635 (2)	0.70369 (9)	0.23471 (19)	0.0245 (4)
H7A	0.5968	0.6724	0.1620	0.029*
H7B	0.6446	0.7485	0.1915	0.029*
C8	0.58034 (17)	0.62208 (8)	0.39595 (17)	0.0188 (3)
C9	0.58804 (18)	0.46384 (8)	0.28764 (18)	0.0204 (3)
H9	0.5641	0.4209	0.3071	0.024*
C10	0.63940 (18)	0.46470 (8)	0.18750 (17)	0.0201 (3)
C11	0.68033 (19)	0.51762 (9)	0.13067 (19)	0.0229 (4)
H11	0.6796	0.5632	0.1538	0.027*
C12	0.65845 (18)	0.40510 (8)	0.12243 (17)	0.0196 (3)
C13	0.63965 (19)	0.33709 (9)	0.13551 (18)	0.0234 (4)
H13	0.6062	0.3216	0.1980	0.028*
C14	0.6707 (2)	0.29284 (9)	0.0556 (2)	0.0276 (4)
H14	0.6595	0.2464	0.0645	0.033*
C15	0.7185 (2)	0.31520 (9)	−0.0383 (2)	0.0285 (4)
H15	0.7380	0.2837	−0.0926	0.034*
C16	0.73753 (19)	0.38186 (9)	−0.05314 (18)	0.0250 (4)
H16	0.7690	0.3972	−0.1173	0.030*
C17	0.70879 (18)	0.42596 (9)	0.02967 (18)	0.0211 (3)
C18	0.8710 (3)	0.54041 (11)	−0.1878 (2)	0.0395 (5)
H18	0.8652	0.4934	−0.1989	0.047*
C19	0.9269 (2)	0.64686 (9)	−0.2527 (2)	0.0294 (4)
H19A	0.9223	0.6613	−0.1685	0.044*
H19B	0.8460	0.6666	−0.3358	0.044*
H19C	1.0193	0.6613	−0.2467	0.044*
C20	0.9516 (2)	0.54244 (10)	−0.3636 (2)	0.0314 (4)
H20A	0.9441	0.4941	−0.3573	0.047*
H20B	1.0510	0.5541	−0.3427	0.047*
H20C	0.8832	0.5573	−0.4587	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01726 (15)	0.01781 (15)	0.01939 (15)	0.00000 (11)	0.01205 (12)	0.00001 (11)
O1	0.0872 (13)	0.0476 (10)	0.0468 (9)	−0.0192 (9)	0.0511 (10)	−0.0044 (7)
S1	0.0345 (3)	0.0189 (2)	0.0316 (2)	−0.00003 (17)	0.0260 (2)	−0.00067 (17)
S2	0.0308 (2)	0.0175 (2)	0.0305 (2)	0.00151 (17)	0.0214 (2)	0.00143 (17)
N1	0.0217 (7)	0.0178 (7)	0.0208 (7)	−0.0002 (5)	0.0126 (6)	0.0020 (6)
N2	0.0222 (7)	0.0179 (7)	0.0214 (7)	−0.0007 (5)	0.0134 (6)	0.0007 (5)
N3	0.0284 (8)	0.0236 (8)	0.0266 (8)	0.0016 (6)	0.0198 (7)	0.0027 (6)
N4	0.0282 (8)	0.0283 (8)	0.0251 (8)	−0.0006 (6)	0.0138 (7)	0.0045 (6)
C1	0.0268 (9)	0.0148 (8)	0.0302 (9)	−0.0002 (7)	0.0175 (8)	0.0050 (7)
C2	0.0309 (10)	0.0290 (10)	0.0281 (9)	−0.0024 (8)	0.0168 (8)	0.0022 (8)
C3	0.0247 (10)	0.0349 (11)	0.0346 (11)	−0.0042 (8)	0.0082 (9)	0.0018 (9)
C4	0.0256 (10)	0.0290 (10)	0.0506 (13)	−0.0022 (8)	0.0207 (10)	−0.0036 (9)
C5	0.0329 (11)	0.0303 (10)	0.0405 (11)	−0.0016 (8)	0.0249 (10)	−0.0031 (8)
C6	0.0285 (9)	0.0252 (9)	0.0290 (9)	−0.0006 (7)	0.0172 (8)	0.0027 (7)
C7	0.0291 (9)	0.0236 (9)	0.0274 (9)	0.0054 (7)	0.0187 (8)	0.0081 (7)
C8	0.0158 (8)	0.0215 (8)	0.0196 (8)	0.0016 (6)	0.0090 (7)	0.0025 (6)
C9	0.0223 (9)	0.0182 (8)	0.0240 (9)	−0.0011 (6)	0.0137 (7)	−0.0003 (7)
C10	0.0214 (8)	0.0197 (8)	0.0212 (8)	−0.0004 (6)	0.0118 (7)	−0.0010 (7)
C11	0.0262 (9)	0.0219 (8)	0.0272 (9)	0.0022 (7)	0.0182 (8)	0.0003 (7)
C12	0.0178 (8)	0.0226 (8)	0.0197 (8)	0.0000 (6)	0.0100 (7)	−0.0026 (7)
C13	0.0223 (9)	0.0239 (9)	0.0259 (9)	−0.0034 (7)	0.0129 (8)	−0.0027 (7)
C14	0.0238 (9)	0.0227 (9)	0.0355 (10)	−0.0022 (7)	0.0135 (8)	−0.0060 (8)
C15	0.0254 (9)	0.0303 (10)	0.0310 (10)	0.0022 (8)	0.0143 (8)	−0.0098 (8)
C16	0.0223 (9)	0.0340 (10)	0.0220 (9)	0.0023 (7)	0.0131 (8)	−0.0034 (7)
C17	0.0192 (8)	0.0237 (9)	0.0210 (8)	0.0025 (7)	0.0101 (7)	−0.0001 (7)
C18	0.0543 (14)	0.0337 (11)	0.0362 (11)	−0.0107 (10)	0.0262 (11)	0.0016 (9)
C19	0.0338 (11)	0.0283 (10)	0.0271 (10)	−0.0031 (8)	0.0154 (9)	0.0030 (8)
C20	0.0308 (10)	0.0354 (11)	0.0312 (10)	0.0037 (8)	0.0173 (9)	0.0028 (8)

Geometric parameters (Å, º) top

Cu1—N2	1.9987 (14)	C5—H5	0.9500
Cu1—N2ⁱ	1.9987 (14)	C6—H6	0.9500
Cu1—S1	2.2666 (4)	C7—H7A	0.9900
Cu1—S1ⁱ	2.2666 (4)	C7—H7B	0.9900
O1—C18	1.234 (3)	C9—C10	1.421 (2)
S1—C8	1.7392 (17)	C9—H9	0.9500
S2—C8	1.7519 (17)	C10—C11	1.394 (2)
S2—C7	1.8092 (17)	C10—C12	1.450 (2)
N1—C8	1.285 (2)	C11—H11	0.9500
N1—N2	1.4048 (18)	C12—C17	1.401 (2)
N2—C9	1.306 (2)	C12—C13	1.397 (2)
N3—C11	1.347 (2)	C13—C14	1.382 (2)
N3—C17	1.381 (2)	C13—H13	0.9500
N3—H3N	0.88 (2)	C14—C15	1.403 (3)
N4—C18	1.321 (2)	C14—H14	0.9500
N4—C19	1.452 (2)	C15—C16	1.374 (3)
N4—C20	1.454 (2)	C15—H15	0.9500
C1—C6	1.390 (2)	C16—C17	1.391 (2)
C1—C2	1.387 (3)	C16—H16	0.9500
C1—C7	1.512 (2)	C18—H18	0.9500
C2—C3	1.386 (3)	C19—H19A	0.9800
C2—H2	0.9500	C19—H19B	0.9800
C3—C4	1.380 (3)	C19—H19C	0.9800
C3—H3	0.9500	C20—H20A	0.9800
C4—C5	1.378 (3)	C20—H20B	0.9800
C4—H4	0.9500	C20—H20C	0.9800
C5—C6	1.386 (3)

N2—Cu1—N2ⁱ	180.000 (1)	S1—C8—S2	112.60 (9)
N2—Cu1—S1	84.21 (4)	N2—C9—C10	130.93 (16)
N2ⁱ—Cu1—S1	95.79 (4)	N2—C9—H9	114.5
N2—Cu1—S1ⁱ	95.79 (4)	C10—C9—H9	114.5
N2ⁱ—Cu1—S1ⁱ	84.21 (4)	C11—C10—C9	130.77 (16)
S1—Cu1—S1ⁱ	180.0	C11—C10—C12	105.86 (15)
C8—S1—Cu1	95.28 (6)	C9—C10—C12	123.36 (15)
C8—S2—C7	104.55 (8)	N3—C11—C10	109.74 (15)
C8—N1—N2	112.72 (13)	N3—C11—H11	125.1
C9—N2—N1	114.11 (14)	C10—C11—H11	125.1
C9—N2—Cu1	124.77 (12)	C17—C12—C13	118.93 (15)
N1—N2—Cu1	121.10 (10)	C17—C12—C10	106.66 (15)
C11—N3—C17	109.91 (15)	C13—C12—C10	134.40 (16)
C11—N3—H3N	124.5 (15)	C14—C13—C12	118.64 (16)
C17—N3—H3N	125.5 (15)	C14—C13—H13	120.7
C18—N4—C19	120.47 (17)	C12—C13—H13	120.7
C18—N4—C20	121.44 (17)	C13—C14—C15	121.20 (17)
C19—N4—C20	118.02 (15)	C13—C14—H14	119.4
C6—C1—C2	118.43 (17)	C15—C14—H14	119.4
C6—C1—C7	117.81 (16)	C16—C15—C14	121.23 (17)
C2—C1—C7	123.75 (16)	C16—C15—H15	119.4
C3—C2—C1	120.16 (18)	C14—C15—H15	119.4
C3—C2—H2	119.9	C15—C16—C17	117.19 (17)
C1—C2—H2	119.9	C15—C16—H16	121.4
C4—C3—C2	120.95 (18)	C17—C16—H16	121.4
C4—C3—H3	119.5	N3—C17—C16	129.38 (16)
C2—C3—H3	119.5	N3—C17—C12	107.84 (14)
C3—C4—C5	119.34 (18)	C16—C17—C12	122.79 (16)
C3—C4—H4	120.3	O1—C18—N4	125.0 (2)
C5—C4—H4	120.3	O1—C18—H18	117.5
C4—C5—C6	119.94 (18)	N4—C18—H18	117.5
C4—C5—H5	120.0	N4—C19—H19A	109.5
C6—C5—H5	120.0	N4—C19—H19B	109.5
C5—C6—C1	121.17 (18)	H19A—C19—H19B	109.5
C5—C6—H6	119.4	N4—C19—H19C	109.5
C1—C6—H6	119.4	H19A—C19—H19C	109.5
C1—C7—S2	118.16 (12)	H19B—C19—H19C	109.5
C1—C7—H7A	107.8	N4—C20—H20A	109.5
S2—C7—H7A	107.8	N4—C20—H20B	109.5
C1—C7—H7B	107.8	H20A—C20—H20B	109.5
S2—C7—H7B	107.8	N4—C20—H20C	109.5
H7A—C7—H7B	107.1	H20A—C20—H20C	109.5
N1—C8—S1	126.61 (13)	H20B—C20—H20C	109.5
N1—C8—S2	120.80 (13)

N2—Cu1—S1—C8	−1.75 (7)	Cu1—N2—C9—C10	−177.95 (14)
N2ⁱ—Cu1—S1—C8	178.25 (7)	N2—C9—C10—C11	−2.0 (3)
C8—N1—N2—C9	178.63 (15)	N2—C9—C10—C12	178.22 (17)
C8—N1—N2—Cu1	−3.25 (19)	C17—N3—C11—C10	0.1 (2)
S1—Cu1—N2—C9	−179.02 (14)	C9—C10—C11—N3	−179.57 (17)
S1ⁱ—Cu1—N2—C9	0.98 (14)	C12—C10—C11—N3	0.2 (2)
S1—Cu1—N2—N1	3.07 (11)	C11—C10—C12—C17	−0.39 (19)
S1ⁱ—Cu1—N2—N1	−176.93 (11)	C9—C10—C12—C17	179.40 (15)
C6—C1—C2—C3	−1.4 (3)	C11—C10—C12—C13	178.57 (19)
C7—C1—C2—C3	−179.70 (17)	C9—C10—C12—C13	−1.6 (3)
C1—C2—C3—C4	1.2 (3)	C17—C12—C13—C14	−0.4 (2)
C2—C3—C4—C5	−0.3 (3)	C10—C12—C13—C14	−179.23 (18)
C3—C4—C5—C6	−0.5 (3)	C12—C13—C14—C15	−0.8 (3)
C4—C5—C6—C1	0.4 (3)	C13—C14—C15—C16	0.7 (3)
C2—C1—C6—C5	0.6 (3)	C14—C15—C16—C17	0.6 (3)
C7—C1—C6—C5	179.01 (16)	C11—N3—C17—C16	179.22 (18)
C6—C1—C7—S2	166.51 (13)	C11—N3—C17—C12	−0.3 (2)
C2—C1—C7—S2	−15.1 (2)	C15—C16—C17—N3	178.73 (17)
C8—S2—C7—C1	−80.69 (15)	C15—C16—C17—C12	−1.8 (3)
N2—N1—C8—S1	1.3 (2)	C13—C12—C17—N3	−178.72 (15)
N2—N1—C8—S2	−179.21 (11)	C10—C12—C17—N3	0.43 (18)
Cu1—S1—C8—N1	0.81 (16)	C13—C12—C17—C16	1.7 (3)
Cu1—S1—C8—S2	−178.73 (8)	C10—C12—C17—C16	−179.15 (16)
C7—S2—C8—N1	5.62 (16)	C19—N4—C18—O1	−0.7 (3)
C7—S2—C8—S1	−174.81 (9)	C20—N4—C18—O1	−177.5 (2)
N1—N2—C9—C10	0.1 (3)

Symmetry code: (i) −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—H3N···O1	0.88 (2)	1.87 (2)	2.742 (2)	175 (2)

Experimental details

Crystal data
Chemical formula	[Cu(C₁₇H₁₄N₃S₂)₂]·2C₃H₇NO
M_r	858.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.4461 (2), 20.0882 (3), 10.8333 (2)
β (°)	118.366 (1)
V (Å³)	2000.34 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.25 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.825, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	18600, 4594, 3837
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.081, 1.04
No. of reflections	4594
No. of parameters	256
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.36

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1	0.88 (2)	1.87 (2)	2.742 (2)	175 (2)

Acknowledgements

We thank the University of Malaya for funding this study (Science Fund grants 12–02-03–2031 and 12–02-03–2051).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008b). Acta Cryst. E64, o2107. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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