(E)-N′-(9-Anthryl­methyl­idene)-p-toluene­sulfono­hydrazide

Asiri, A.M.; Zayed, M.E.M.; Ng, S.W.

doi:10.1107/S160053681003271X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2361

https://doi.org/10.1107/S160053681003271X

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(E)-N′-(9-Anthrylmethylidene)-p-toluenesulfonohydrazide

Abdullah M. Asiri,^a Mohie E. M. Zayed ^a and Seik Weng Ng ^b ^*

^aChemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 12 August 2010; accepted 14 August 2010; online 21 August 2010)

The S—N(H)—N=C linkage in the title molecule, C₂₂H₁₈N₂O₂S, is non-planar [torsion angle = 30.6 (1)°] as the amino N atom is pyramidally coordinated. In the crystal, the amino group acts as a hydrogen-bond donor to an O atom of an adjacent molecule, generating chains running parallel to the b axis.

Related literature

For the structure of the (E)-N′-benzylidene-p-toluenesulfonohydrazide analog, see: Mehrabi et al. (2008 ).

Experimental

Crystal data

C₂₂H₁₈N₂O₂S
M_r = 374.44
Orthorhombic, P b c a
a = 17.3634 (15) Å
b = 9.2438 (8) Å
c = 22.882 (2) Å
V = 3672.6 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100 K
0.40 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.926, T_max = 0.990
22220 measured reflections
4209 independent reflections
3158 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.104
S = 1.02
4209 reflections
249 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86 (1)	2.07 (1)	2.911 (2)	169 (2)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681003271X/pk2262sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003271X/pk2262Isup2.hkl

checkCIF report

Comment top

p-Toluenesulfonyl hydrazide, CH₃-4-C₆H₄SO₂NHNH₂, condenses with carbonyl compounds to form Schiff bases, and among the plethora, nearly a hundred have had their crystal structures determined. The compounds have the azomethine double-bond in an E-configuration. In the Schiff base product between p-toluenesulfonyl hydrazide and thiophene-2-carboxaldehyde, the S–N(H)–N═C linkage is non-planar [torsion angle 30.6 (1) °] as the amino nitrogen atom (which bears a hydrogen atom) is pyramidally coordinated (Fig. 1). The amino group acts as a hydrogen-bond donor to an oxygen atom of an adjacent molecule to generate chains running parallel to the b-axis of the cell (Fig. 2).

Related literature top

For the structure of the (E)-N'-benzylidene-p-toluenesulfonohydrazide homolog, see: Mehrabi et al. (2008).

Experimental top

p-Toluenesulfonyl hydrazide (4.66 g, 2.5 mmol) and anthracene-9-carboxaldehyde (5.162.80 g, 2.5 mmol) were heated in methanol (50 ml) for two hours. The cool solution yielded a precipitate that was recrystallized from ethanol and collected in 90% yield.

Structure description top

For the structure of the (E)-N'-benzylidene-p-toluenesulfonohydrazide homolog, see: Mehrabi et al. (2008).

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₂H₁₈N₂O₂S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. A view of the chain structure resulting from N—H···O hydrogen-bonding.

(E)-N'-(9-Anthrylmethylidene)-p-toluenesulfonohydrazide top

Crystal data top

C₂₂H₁₈N₂O₂S	F(000) = 1568
M_r = 374.44	D_x = 1.354 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3593 reflections
a = 17.3634 (15) Å	θ = 2.3–27.6°
b = 9.2438 (8) Å	µ = 0.20 mm⁻¹
c = 22.882 (2) Å	T = 100 K
V = 3672.6 (6) Å³	Prism, yellow
Z = 8	0.40 × 0.20 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	4209 independent reflections
Radiation source: fine-focus sealed tube	3158 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→22
T_min = 0.926, T_max = 0.990	k = −12→10
22220 measured reflections	l = −29→29

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0442P)² + 1.8913P] where P = (F_o² + 2F_c²)/3
4209 reflections	(Δ/σ)_max = 0.001
249 parameters	Δρ_max = 0.34 e Å⁻³
1 restraint	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₂₂H₁₈N₂O₂S	V = 3672.6 (6) Å³
M_r = 374.44	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.3634 (15) Å	µ = 0.20 mm⁻¹
b = 9.2438 (8) Å	T = 100 K
c = 22.882 (2) Å	0.40 × 0.20 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	4209 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3158 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.990	R_int = 0.055
22220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.34 e Å⁻³
4209 reflections	Δρ_min = −0.46 e Å⁻³
249 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.70021 (2)	0.57688 (5)	0.781940 (19)	0.01816 (12)
O1	0.67930 (7)	0.71367 (13)	0.75666 (6)	0.0228 (3)
O2	0.75969 (7)	0.57170 (14)	0.82533 (5)	0.0244 (3)
N1	0.73235 (8)	0.47229 (17)	0.72874 (6)	0.0188 (3)
H1	0.7581 (11)	0.4002 (17)	0.7419 (9)	0.032 (6)*
N2	0.67630 (8)	0.44447 (16)	0.68590 (6)	0.0187 (3)
C1	0.61574 (10)	0.4956 (2)	0.80808 (8)	0.0207 (4)
C2	0.54464 (11)	0.5595 (2)	0.79729 (9)	0.0263 (4)
H2	0.5412	0.6474	0.7760	0.032*
C3	0.47881 (11)	0.4919 (2)	0.81839 (9)	0.0324 (5)
H3	0.4299	0.5341	0.8111	0.039*
C4	0.48310 (12)	0.3638 (2)	0.84988 (9)	0.0319 (5)
C5	0.55497 (13)	0.3014 (2)	0.85908 (9)	0.0326 (5)
H5	0.5584	0.2129	0.8800	0.039*
C6	0.62165 (11)	0.3659 (2)	0.83825 (8)	0.0256 (4)
H6	0.6705	0.3220	0.8445	0.031*
C7	0.41088 (13)	0.2933 (3)	0.87297 (10)	0.0437 (6)
H7A	0.3755	0.3679	0.8872	0.066*
H7B	0.4242	0.2279	0.9051	0.066*
H7C	0.3861	0.2382	0.8416	0.066*
C8	0.68260 (10)	0.32154 (19)	0.66045 (7)	0.0190 (4)
H8	0.7224	0.2580	0.6727	0.023*
C9	0.63107 (10)	0.27431 (19)	0.61321 (7)	0.0181 (4)
C10	0.55246 (10)	0.31693 (19)	0.61075 (8)	0.0196 (4)
C11	0.51458 (10)	0.3970 (2)	0.65569 (8)	0.0225 (4)
H11	0.5434	0.4292	0.6885	0.027*
C12	0.43788 (11)	0.4284 (2)	0.65260 (9)	0.0256 (4)
H12	0.4139	0.4789	0.6839	0.031*
C13	0.39353 (11)	0.3870 (2)	0.60350 (9)	0.0284 (4)
H13	0.3406	0.4124	0.6013	0.034*
C14	0.42673 (11)	0.3113 (2)	0.55987 (9)	0.0274 (4)
H14	0.3968	0.2849	0.5268	0.033*
C15	0.50621 (10)	0.2698 (2)	0.56239 (8)	0.0232 (4)
C16	0.53801 (11)	0.1800 (2)	0.51995 (8)	0.0248 (4)
H16	0.5071	0.1511	0.4877	0.030*
C17	0.61374 (10)	0.1311 (2)	0.52330 (8)	0.0207 (4)
C18	0.64417 (11)	0.0329 (2)	0.48093 (8)	0.0249 (4)
H18	0.6121	0.0005	0.4500	0.030*
C19	0.71804 (11)	−0.0149 (2)	0.48399 (8)	0.0247 (4)
H19	0.7372	−0.0808	0.4557	0.030*
C20	0.76612 (11)	0.0344 (2)	0.52973 (8)	0.0229 (4)
H20	0.8179	0.0017	0.5316	0.028*
C21	0.73965 (10)	0.1276 (2)	0.57109 (8)	0.0204 (4)
H21	0.7736	0.1594	0.6010	0.025*
C22	0.66168 (10)	0.17906 (19)	0.57053 (7)	0.0184 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0166 (2)	0.0169 (2)	0.0210 (2)	−0.00194 (17)	0.00059 (17)	−0.00158 (17)
O1	0.0222 (7)	0.0163 (6)	0.0300 (7)	−0.0008 (5)	0.0016 (5)	0.0003 (5)
O2	0.0203 (7)	0.0287 (7)	0.0241 (7)	−0.0025 (6)	−0.0044 (5)	−0.0040 (6)
N1	0.0164 (7)	0.0189 (8)	0.0211 (8)	0.0014 (6)	−0.0012 (6)	−0.0008 (6)
N2	0.0167 (7)	0.0209 (8)	0.0184 (7)	−0.0022 (6)	−0.0009 (6)	−0.0003 (6)
C1	0.0204 (9)	0.0205 (9)	0.0212 (9)	−0.0052 (7)	0.0050 (7)	−0.0043 (7)
C2	0.0219 (9)	0.0249 (10)	0.0323 (10)	−0.0008 (8)	0.0037 (8)	−0.0067 (8)
C3	0.0222 (10)	0.0366 (12)	0.0386 (12)	−0.0036 (9)	0.0077 (9)	−0.0149 (10)
C4	0.0330 (11)	0.0353 (12)	0.0274 (10)	−0.0164 (9)	0.0122 (9)	−0.0173 (9)
C5	0.0449 (13)	0.0250 (11)	0.0279 (10)	−0.0115 (9)	0.0087 (9)	−0.0030 (9)
C6	0.0296 (10)	0.0220 (10)	0.0252 (9)	−0.0029 (8)	0.0049 (8)	−0.0017 (8)
C7	0.0381 (13)	0.0554 (16)	0.0375 (12)	−0.0261 (11)	0.0144 (10)	−0.0162 (11)
C8	0.0177 (9)	0.0198 (9)	0.0195 (9)	0.0003 (7)	0.0016 (7)	0.0035 (7)
C9	0.0190 (9)	0.0171 (9)	0.0182 (8)	−0.0017 (7)	0.0004 (7)	0.0026 (7)
C10	0.0187 (9)	0.0184 (9)	0.0216 (9)	−0.0010 (7)	−0.0008 (7)	0.0031 (7)
C11	0.0197 (9)	0.0241 (10)	0.0238 (9)	−0.0020 (7)	0.0005 (7)	−0.0015 (8)
C12	0.0220 (9)	0.0249 (10)	0.0300 (10)	0.0017 (8)	0.0035 (8)	−0.0020 (8)
C13	0.0184 (9)	0.0299 (11)	0.0369 (11)	0.0042 (8)	−0.0030 (8)	0.0015 (9)
C14	0.0229 (10)	0.0311 (11)	0.0282 (10)	0.0044 (8)	−0.0083 (8)	−0.0004 (9)
C15	0.0213 (9)	0.0248 (10)	0.0235 (9)	0.0015 (8)	−0.0036 (7)	0.0035 (8)
C16	0.0243 (10)	0.0297 (10)	0.0203 (9)	0.0018 (8)	−0.0067 (8)	−0.0007 (8)
C17	0.0222 (9)	0.0218 (9)	0.0182 (8)	0.0009 (7)	−0.0005 (7)	0.0022 (7)
C18	0.0274 (10)	0.0283 (10)	0.0191 (9)	−0.0004 (8)	−0.0040 (8)	−0.0010 (8)
C19	0.0289 (10)	0.0252 (10)	0.0200 (9)	0.0015 (8)	0.0039 (8)	−0.0007 (8)
C20	0.0199 (9)	0.0231 (10)	0.0258 (10)	0.0020 (7)	0.0023 (7)	0.0031 (8)
C21	0.0193 (9)	0.0210 (9)	0.0210 (8)	−0.0010 (7)	0.0005 (7)	0.0019 (7)
C22	0.0199 (9)	0.0176 (9)	0.0176 (8)	−0.0018 (7)	0.0001 (7)	0.0046 (7)

Geometric parameters (Å, º) top

S1—O1	1.4370 (13)	C9—C10	1.422 (2)
S1—O2	1.4334 (13)	C10—C11	1.428 (2)
S1—N1	1.6516 (15)	C10—C15	1.435 (2)
S1—C1	1.7532 (18)	C11—C12	1.365 (3)
N1—N2	1.405 (2)	C11—H11	0.9500
N1—H1	0.857 (9)	C12—C13	1.415 (3)
N2—C8	1.281 (2)	C12—H12	0.9500
C1—C6	1.387 (3)	C13—C14	1.349 (3)
C1—C2	1.391 (3)	C13—H13	0.9500
C2—C3	1.389 (3)	C14—C15	1.434 (3)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.388 (3)	C15—C16	1.392 (3)
C3—H3	0.9500	C16—C17	1.392 (3)
C4—C5	1.391 (3)	C16—H16	0.9500
C4—C7	1.509 (3)	C17—C18	1.429 (3)
C5—C6	1.387 (3)	C17—C22	1.434 (2)
C5—H5	0.9500	C18—C19	1.358 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—H7A	0.9800	C19—C20	1.414 (3)
C7—H7B	0.9800	C19—H19	0.9500
C7—H7C	0.9800	C20—C21	1.360 (2)
C8—C9	1.470 (2)	C20—H20	0.9500
C8—H8	0.9500	C21—C22	1.435 (2)
C9—C22	1.418 (2)	C21—H21	0.9500

O1—S1—O2	119.35 (8)	C9—C10—C11	123.88 (16)
O1—S1—N1	107.68 (8)	C9—C10—C15	118.93 (16)
O2—S1—N1	104.33 (8)	C11—C10—C15	117.07 (16)
O1—S1—C1	107.65 (8)	C12—C11—C10	121.50 (18)
O2—S1—C1	110.62 (8)	C12—C11—H11	119.3
N1—S1—C1	106.45 (8)	C10—C11—H11	119.3
N2—N1—S1	112.79 (11)	C11—C12—C13	120.98 (18)
N2—N1—H1	117.7 (15)	C11—C12—H12	119.5
S1—N1—H1	111.8 (14)	C13—C12—H12	119.5
C8—N2—N1	114.84 (15)	C14—C13—C12	119.71 (17)
C6—C1—C2	121.41 (17)	C14—C13—H13	120.1
C6—C1—S1	118.58 (14)	C12—C13—H13	120.1
C2—C1—S1	120.00 (15)	C13—C14—C15	121.36 (18)
C3—C2—C1	118.52 (19)	C13—C14—H14	119.3
C3—C2—H2	120.7	C15—C14—H14	119.3
C1—C2—H2	120.7	C16—C15—C10	119.80 (16)
C4—C3—C2	121.3 (2)	C16—C15—C14	120.89 (17)
C4—C3—H3	119.3	C10—C15—C14	119.26 (17)
C2—C3—H3	119.3	C17—C16—C15	122.00 (17)
C3—C4—C5	118.72 (18)	C17—C16—H16	119.0
C3—C4—C7	120.4 (2)	C15—C16—H16	119.0
C5—C4—C7	120.9 (2)	C16—C17—C18	121.19 (17)
C6—C5—C4	121.3 (2)	C16—C17—C22	119.28 (17)
C6—C5—H5	119.4	C18—C17—C22	119.52 (16)
C4—C5—H5	119.4	C19—C18—C17	121.39 (17)
C5—C6—C1	118.73 (19)	C19—C18—H18	119.3
C5—C6—H6	120.6	C17—C18—H18	119.3
C1—C6—H6	120.6	C18—C19—C20	119.38 (17)
C4—C7—H7A	109.5	C18—C19—H19	120.3
C4—C7—H7B	109.5	C20—C19—H19	120.3
H7A—C7—H7B	109.5	C21—C20—C19	121.31 (17)
C4—C7—H7C	109.5	C21—C20—H20	119.3
H7A—C7—H7C	109.5	C19—C20—H20	119.3
H7B—C7—H7C	109.5	C20—C21—C22	121.52 (17)
N2—C8—C9	123.06 (16)	C20—C21—H21	119.2
N2—C8—H8	118.5	C22—C21—H21	119.2
C9—C8—H8	118.5	C9—C22—C21	123.60 (16)
C22—C9—C10	120.31 (16)	C9—C22—C17	119.55 (16)
C22—C9—C8	117.56 (15)	C21—C22—C17	116.85 (16)
C10—C9—C8	122.09 (16)

O1—S1—N1—N2	−62.00 (13)	C10—C11—C12—C13	−2.3 (3)
O2—S1—N1—N2	170.23 (11)	C11—C12—C13—C14	2.1 (3)
C1—S1—N1—N2	53.21 (14)	C12—C13—C14—C15	0.9 (3)
S1—N1—N2—C8	−149.39 (13)	C9—C10—C15—C16	2.1 (3)
O1—S1—C1—C6	−175.60 (14)	C11—C10—C15—C16	−174.03 (17)
O2—S1—C1—C6	−43.59 (17)	C9—C10—C15—C14	179.46 (17)
N1—S1—C1—C6	69.17 (16)	C11—C10—C15—C14	3.4 (3)
O1—S1—C1—C2	5.81 (18)	C13—C14—C15—C16	173.73 (19)
O2—S1—C1—C2	137.82 (15)	C13—C14—C15—C10	−3.6 (3)
N1—S1—C1—C2	−109.42 (16)	C10—C15—C16—C17	1.3 (3)
C6—C1—C2—C3	1.2 (3)	C14—C15—C16—C17	−176.08 (18)
S1—C1—C2—C3	179.71 (15)	C15—C16—C17—C18	176.73 (18)
C1—C2—C3—C4	0.3 (3)	C15—C16—C17—C22	−2.6 (3)
C2—C3—C4—C5	−1.4 (3)	C16—C17—C18—C19	179.93 (18)
C2—C3—C4—C7	179.28 (18)	C22—C17—C18—C19	−0.8 (3)
C3—C4—C5—C6	1.0 (3)	C17—C18—C19—C20	−0.6 (3)
C7—C4—C5—C6	−179.68 (18)	C18—C19—C20—C21	0.7 (3)
C4—C5—C6—C1	0.4 (3)	C19—C20—C21—C22	0.6 (3)
C2—C1—C6—C5	−1.6 (3)	C10—C9—C22—C21	−177.99 (16)
S1—C1—C6—C5	179.88 (14)	C8—C9—C22—C21	−0.2 (3)
N1—N2—C8—C9	−178.04 (15)	C10—C9—C22—C17	2.8 (3)
N2—C8—C9—C22	149.92 (17)	C8—C9—C22—C17	−179.43 (15)
N2—C8—C9—C10	−32.4 (3)	C20—C21—C22—C9	178.91 (17)
C22—C9—C10—C11	171.73 (17)	C20—C21—C22—C17	−1.9 (3)
C8—C9—C10—C11	−5.9 (3)	C16—C17—C22—C9	0.5 (3)
C22—C9—C10—C15	−4.1 (3)	C18—C17—C22—C9	−178.81 (17)
C8—C9—C10—C15	178.27 (16)	C16—C17—C22—C21	−178.75 (17)
C9—C10—C11—C12	−176.38 (18)	C18—C17—C22—C21	1.9 (2)
C15—C10—C11—C12	−0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86 (1)	2.07 (1)	2.911 (2)	169 (2)

Symmetry code: (i) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈N₂O₂S
M_r	374.44
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	17.3634 (15), 9.2438 (8), 22.882 (2)
V (Å³)	3672.6 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.40 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.926, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	22220, 4209, 3158
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.104, 1.02
No. of reflections	4209
No. of parameters	249
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.46

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86 (1)	2.07 (1)	2.911 (2)	169 (2)

Symmetry code: (i) −x+3/2, y−1/2, z.

Acknowledgements

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mehrabi, H., Kia, R., Hassanzadeh, A., Ghobadi, S. & Khavasi, H. R. (2008). Acta Cryst. E64, o1845. 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. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar