(E)-N′-Benzyl­idene-p-toluene­sulfono­hydrazide

Mehrabi, H.; Kia, R.; Hassanzadeh, A.; Ghobadi, S.; Khavasi, H.R.

doi:10.1107/S1600536808027219

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1845

doi:10.1107/S1600536808027219

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(E)-N′-Benzylidene-p-toluenesulfonohydrazide

Hossein Mehrabi,^a ^* Reza Kia,^b ‡ Ali Hassanzadeh,^c Samaneh Ghobadi ^c and Hamid Reza Khavasi ^d

^aDepartment of Chemistry, Vali-e-Asr University of Rafsanjan, Rafsanjan, 77176, Iran, ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^cDepartment of Chemistry, Faculty of Science, Urmia University, Urmia, Iran, and ^dDepartment of Chemistry, Faculty of Science, Shahid Beheshti University, Tehran, Iran
^*Correspondence e-mail: mehraby_h@yahoo.com

(Received 17 August 2008; accepted 23 August 2008; online 30 August 2008)

In the title compound, C₁₄H₁₄N₂O₂S, a novel sulfonamide derivative, an intramolecular C—H⋯O hydrogen bond generates an S(5) ring motif. The molecule adopts a twisted E configuration around the C=N bond. An intermolecular N—H⋯O hydrogen bond generates an R²₂(8) ring motif. The dihedral angle between the rings is 85.37 (9)°. The H atoms of the methyl group have rotational disorder with refined site occupancies of ca 0.63/0.37. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link neighbouring molecules into dimers which stack along the a axis with a centroid–centroid distance of 3.8856 (10) Å.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures and applications, see, for example: Tabatabaee et al. (2007 ); Ali et al. (2007 ); Tierney et al. (2006 ); Krygowski et al. (1998 ); Kayser et al. (2004 ).

Experimental

Crystal data

C₁₄H₁₄N₂O₂S
M_r = 274.33
Monoclinic, P 2₁ /c
a = 5.9593 (7) Å
b = 9.6592 (7) Å
c = 23.712 (3) Å
β = 91.533 (9)°
V = 1364.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 (2) K
0.50 × 0.40 × 0.03 mm

Data collection

STOE IPDSII diffractometer
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2004 ) T_min = 0.879, T_max = 0.993
8939 measured reflections
3573 independent reflections
3008 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.110
S = 1.10
3573 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.863 (19)	2.082 (19)	2.9446 (17)	177.0 (18)
C5—H5A⋯O2	0.93	2.54	2.9133 (18)	104
Symmetry code: (i) -x+1, -y, -z.

Data collection: X-AREA (Stoe & Cie, 2005 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek,2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027219/at2617sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027219/at2617Isup2.hkl

checkCIF report

Comment top

Sulfonamides were the first class of antimicrobial agents to be discovered. They inhibit dihydropteroate synthetase in the bacterial folic acid pathway. Although their clinical role has diminished, they are still useful in certain situations, because of its efficacy and low cost (Krygowski et al., 1998). Sulfonamides (sulfanilamide, sulfamethoxazole, sulfafurazole) are structural analogs of p-aminobenzoic acid (PABA) and compete with PABA to block its conversion to dihydrofolic acid. These agents are generally used in combination with other drugs (usually sulfonamides) to prevent or treat a number of bacterial and parasitic infections (Tierney et al., 2006). Some of the applications of sulfonamides are the anti-infective agents of choice, as follows: Bacteria as Human Pathogens, such as Antibiotic Treatment of Infections Caused by Gram-Positive Bacilli and Gram-negative Haemophilus ducreyi and Haemophilus aegyptius, Alternative Drug for treatment of Chlamydia related diseases (including C. trachomatis, Chlamydia psittaci, Chlamydia pneumonia), Anti-malarial Agents as Dihydropteroate synthetase inhibitors, alternative drugs in tuberculosis treatment, long term treatment of leprosy, treatment of ocular infections. In the latter treatment causative organisms must be identified, and it is preferable to use a drug that is not given systemically. Sulfonamides are also assumed as permitted antibiotics in Pregnancy (Kayser et al., 2004).

The title compound (I) (Fig. 1), is a novel sulfonamide derivative. Bond lengths and angles are within the normal ranges (Allen et al., 1987) and are comparable with the similar staructures (Ali et al. 2007). An intramolecular C—H···O hydrogen bond generate S(5) ring motif (Bernstein et al., 1995). The molecule adopts a twisted E configuration around the C═N. An intermolecular N—H···O hydrogen bond genarate R²₂(8) ring motif (Bernstein et al., 1995). The dihedral angle between the phenyl rings is 85.37 (9)°. None of the H atoms of the methyl group was clearly resolved in the difference Fourier map and they were disordered over six positions and refined with site-occupancy factors of 0.62 (3) and 0.38 (3) for the major and minor componenets, respectively. In the crystal structure, intermolecular N—H···O interactions link neighbouring molecules into dimers which stacked along the a-axis. The short distance between the centroids of the six-membered rings prove an exsistence of the π-π interactions with centroid to centroid dsiatnce of 3.8856 (10) Å. The crystal structure is stabilized by intramolecular C—H···O, intermolecular N—H···O hydrogen bonds and π-π satcking.

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures and applications, see, for example: Tabatabaee et al. (2007); Ali et al. (2007); Tierney et al. (2006); Krygowski et al. (1998); Kayser et al. (2004).

Experimental top

p-Tosylhydrazine (3 mmol) was added to a stirred solution of benzaldehyde (3 mmol) in 2 ml of toluene at 20–25° C. The mixture was stirred for 6 h at 110° C. After cooling, the colorless crystalline solid was isolated by filtration, washed with cold toluene, and re-crystallized from ethanol.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek,2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. Open bonds indicate the minor disordered component. Intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the major component of (I), viewed down the a-axis, showing staking arrangement of molecules. Intermolecular and intermolecular hydrogen bonds are shown as dashed line.

(E)-N'-Benzylidene-p-toluenesulfonohydrazide top

Crystal data top

C₁₄H₁₄N₂O₂S	F(000) = 576
M_r = 274.33	D_x = 1.336 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2500 reflections
a = 5.9593 (7) Å	θ = 2.3–29.2°
b = 9.6592 (7) Å	µ = 0.24 mm⁻¹
c = 23.712 (3) Å	T = 293 K
β = 91.533 (9)°	Plate, colourless
V = 1364.4 (3) Å³	0.50 × 0.40 × 0.03 mm
Z = 4

Data collection top

STOE IPDSII diffractometer	3573 independent reflections
Radiation source: fine-focus sealed tube	3008 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 0.15 pixels mm^-1	θ_max = 29.0°, θ_min = 2.3°
ϕ scans	h = −8→6
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2004)	k = −12→13
T_min = 0.879, T_max = 0.993	l = −32→32
8939 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0507P)² + 0.2385P] where P = (F_o² + 2F_c²)/3
3573 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₂S	V = 1364.4 (3) Å³
M_r = 274.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.9593 (7) Å	µ = 0.24 mm⁻¹
b = 9.6592 (7) Å	T = 293 K
c = 23.712 (3) Å	0.50 × 0.40 × 0.03 mm
β = 91.533 (9)°

Data collection top

STOE IPDSII diffractometer	3573 independent reflections
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2004)	3008 reflections with I > 2σ(I)
T_min = 0.879, T_max = 0.993	R_int = 0.026
8939 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.23 e Å⁻³
3573 reflections	Δρ_min = −0.25 e Å⁻³
195 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	Occ. (<1)
S1	0.24869 (6)	0.18884 (4)	0.001194 (15)	0.04475 (12)
O1	0.39754 (19)	0.13796 (12)	−0.04087 (4)	0.0555 (3)
O2	0.03368 (18)	0.24148 (12)	−0.01555 (5)	0.0572 (3)
N1	0.2191 (2)	0.05429 (14)	0.04190 (6)	0.0531 (3)
H1N1	0.328 (3)	−0.004 (2)	0.0425 (8)	0.063 (5)*
N2	0.0856 (2)	0.06535 (13)	0.08855 (6)	0.0500 (3)
C1	0.6026 (2)	0.28675 (16)	0.06340 (7)	0.0504 (3)
H1A	0.6706	0.2023	0.0558	0.060*
C2	0.7124 (3)	0.38438 (18)	0.09592 (7)	0.0565 (4)
H2A	0.8548	0.3648	0.1108	0.068*
C3	0.6147 (3)	0.51220 (17)	0.10705 (6)	0.0542 (4)
C4	0.4028 (3)	0.53993 (16)	0.08404 (7)	0.0551 (4)
H4A	0.3367	0.6255	0.0905	0.066*
C5	0.2883 (2)	0.44255 (15)	0.05169 (6)	0.0480 (3)
H5A	0.1460	0.4619	0.0367	0.058*
C6	0.3884 (2)	0.31589 (14)	0.04191 (6)	0.0418 (3)
C7	0.1133 (3)	−0.03135 (15)	0.12464 (7)	0.0509 (3)
H7A	0.2260	−0.0962	0.1192	0.061*
C8	−0.0264 (3)	−0.04390 (16)	0.17434 (6)	0.0516 (3)
C9	0.0359 (3)	−0.1379 (2)	0.21640 (7)	0.0655 (4)
H9A	0.1678	−0.1885	0.2134	0.079*
C10	−0.0980 (5)	−0.1566 (3)	0.26284 (8)	0.0807 (6)
H10A	−0.0555	−0.2196	0.2908	0.097*
C11	−0.2921 (5)	−0.0825 (3)	0.26759 (9)	0.0884 (7)
H11A	−0.3815	−0.0953	0.2987	0.106*
C12	−0.3558 (4)	0.0115 (3)	0.22621 (10)	0.0858 (6)
H12A	−0.4876	0.0620	0.2296	0.103*
C13	−0.2239 (3)	0.0303 (2)	0.17986 (8)	0.0677 (5)
H13A	−0.2679	0.0933	0.1521	0.081*
C14	0.7396 (5)	0.6169 (3)	0.14314 (10)	0.0776 (6)
H14A	0.651 (10)	0.695 (7)	0.147 (3)	0.116*	0.63 (4)
H14B	0.855 (10)	0.656 (7)	0.124 (2)	0.116*	0.63 (4)
H14C	0.789 (11)	0.581 (6)	0.177 (2)	0.116*	0.63 (4)
H14D	0.73 (2)	0.714 (12)	0.128 (4)	0.116*	0.37 (4)
H14E	0.920 (16)	0.579 (9)	0.151 (4)	0.116*	0.37 (4)
H14F	0.648 (17)	0.625 (10)	0.185 (4)	0.116*	0.37 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.04108 (18)	0.04409 (19)	0.04919 (19)	0.00320 (13)	0.00301 (13)	−0.00108 (14)
O1	0.0593 (6)	0.0565 (6)	0.0512 (5)	0.0086 (5)	0.0097 (5)	−0.0032 (5)
O2	0.0440 (6)	0.0602 (6)	0.0668 (7)	0.0048 (5)	−0.0070 (5)	−0.0030 (5)
N1	0.0518 (7)	0.0427 (6)	0.0656 (8)	0.0037 (5)	0.0150 (6)	0.0018 (6)
N2	0.0461 (6)	0.0451 (6)	0.0592 (7)	−0.0026 (5)	0.0096 (5)	−0.0020 (5)
C1	0.0421 (7)	0.0527 (8)	0.0564 (8)	0.0078 (6)	0.0017 (6)	0.0020 (6)
C2	0.0445 (7)	0.0672 (10)	0.0573 (8)	−0.0030 (7)	−0.0046 (6)	0.0058 (7)
C3	0.0606 (9)	0.0558 (8)	0.0463 (7)	−0.0140 (7)	0.0025 (6)	0.0044 (6)
C4	0.0635 (9)	0.0421 (7)	0.0600 (8)	0.0010 (6)	0.0065 (7)	0.0005 (6)
C5	0.0424 (7)	0.0448 (7)	0.0568 (8)	0.0051 (5)	0.0011 (6)	0.0043 (6)
C6	0.0376 (6)	0.0437 (7)	0.0442 (6)	0.0017 (5)	0.0049 (5)	0.0045 (5)
C7	0.0494 (8)	0.0433 (7)	0.0601 (8)	−0.0005 (6)	0.0041 (6)	−0.0039 (6)
C8	0.0559 (8)	0.0472 (7)	0.0515 (7)	−0.0083 (6)	0.0007 (6)	−0.0062 (6)
C9	0.0745 (11)	0.0648 (10)	0.0568 (9)	−0.0035 (9)	−0.0053 (8)	−0.0001 (8)
C10	0.1072 (17)	0.0847 (14)	0.0501 (9)	−0.0107 (12)	−0.0013 (10)	0.0050 (9)
C11	0.1082 (18)	0.1013 (17)	0.0570 (10)	−0.0159 (14)	0.0253 (11)	−0.0081 (11)
C12	0.0802 (14)	0.0963 (16)	0.0823 (13)	0.0054 (12)	0.0281 (11)	−0.0057 (12)
C13	0.0655 (11)	0.0687 (11)	0.0695 (10)	0.0047 (8)	0.0135 (8)	0.0040 (9)
C14	0.0961 (17)	0.0716 (13)	0.0646 (11)	−0.0275 (12)	−0.0085 (11)	−0.0039 (10)

Geometric parameters (Å, º) top

S1—O2	1.4250 (11)	C7—H7A	0.9300
S1—O1	1.4389 (11)	C8—C13	1.387 (3)
S1—N1	1.6313 (14)	C8—C9	1.392 (2)
S1—C6	1.7573 (14)	C9—C10	1.389 (3)
N1—N2	1.3840 (18)	C9—H9A	0.9300
N1—H1N1	0.86 (2)	C10—C11	1.368 (4)
N2—C7	1.274 (2)	C10—H10A	0.9300
C1—C2	1.373 (2)	C11—C12	1.382 (3)
C1—C6	1.3908 (19)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.380 (3)
C2—C3	1.393 (2)	C12—H12A	0.9300
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.388 (2)	C14—H14A	0.93 (7)
C3—C14	1.509 (2)	C14—H14B	0.92 (6)
C4—C5	1.382 (2)	C14—H14C	0.92 (6)
C4—H4A	0.9300	C14—H14D	1.00 (11)
C5—C6	1.3832 (19)	C14—H14E	1.15 (10)
C5—H5A	0.9300	C14—H14F	1.15 (10)
C7—C8	1.466 (2)

O2—S1—O1	119.68 (7)	C10—C9—H9A	119.8
O2—S1—N1	109.79 (7)	C8—C9—H9A	119.8
O1—S1—N1	102.50 (7)	C11—C10—C9	120.2 (2)
O2—S1—C6	108.24 (7)	C11—C10—H10A	119.9
O1—S1—C6	109.13 (7)	C9—C10—H10A	119.9
N1—S1—C6	106.76 (7)	C10—C11—C12	120.1 (2)
N2—N1—S1	119.01 (10)	C10—C11—H11A	119.9
N2—N1—H1N1	119.1 (13)	C12—C11—H11A	119.9
S1—N1—H1N1	116.1 (13)	C13—C12—C11	120.0 (2)
C7—N2—N1	114.41 (13)	C13—C12—H12A	120.0
C2—C1—C6	119.05 (14)	C11—C12—H12A	120.0
C2—C1—H1A	120.5	C12—C13—C8	120.64 (19)
C6—C1—H1A	120.5	C12—C13—H13A	119.7
C1—C2—C3	121.33 (14)	C8—C13—H13A	119.7
C1—C2—H2A	119.3	C3—C14—H14A	109 (4)
C3—C2—H2A	119.3	C3—C14—H14B	111 (3)
C4—C3—C2	118.47 (14)	H14A—C14—H14B	99 (4)
C4—C3—C14	121.57 (19)	C3—C14—H14C	113 (3)
C2—C3—C14	119.96 (19)	H14A—C14—H14C	112 (5)
C5—C4—C3	121.13 (15)	H14B—C14—H14C	112 (5)
C5—C4—H4A	119.4	C3—C14—H14D	113 (5)
C3—C4—H4A	119.4	H14A—C14—H14D	41 (6)
C4—C5—C6	119.10 (14)	H14B—C14—H14D	59 (5)
C4—C5—H5A	120.4	H14C—C14—H14D	133 (6)
C6—C5—H5A	120.4	C3—C14—H14E	109 (4)
C5—C6—C1	120.88 (14)	H14A—C14—H14E	141 (5)
C5—C6—S1	120.65 (11)	H14B—C14—H14E	60 (4)
C1—C6—S1	118.47 (11)	H14C—C14—H14E	58 (4)
N2—C7—C8	122.31 (14)	H14D—C14—H14E	114 (7)
N2—C7—H7A	118.8	C3—C14—H14F	108 (4)
C8—C7—H7A	118.8	H14A—C14—H14F	64 (5)
C13—C8—C9	118.70 (16)	H14B—C14—H14F	141 (5)
C13—C8—C7	122.31 (15)	H14C—C14—H14F	54 (4)
C9—C8—C7	118.94 (16)	H14D—C14—H14F	102 (7)
C10—C9—C8	120.3 (2)	H14E—C14—H14F	110 (6)

O2—S1—N1—N2	−52.51 (14)	N1—S1—C6—C5	−119.42 (12)
O1—S1—N1—N2	179.27 (11)	O2—S1—C6—C1	179.55 (11)
C6—S1—N1—N2	64.61 (13)	O1—S1—C6—C1	−48.69 (13)
S1—N1—N2—C7	−164.31 (11)	N1—S1—C6—C1	61.41 (13)
C6—C1—C2—C3	−0.9 (2)	N1—N2—C7—C8	−174.66 (13)
C1—C2—C3—C4	−0.5 (2)	N2—C7—C8—C13	13.1 (2)
C1—C2—C3—C14	179.77 (17)	N2—C7—C8—C9	−169.75 (15)
C2—C3—C4—C5	1.2 (2)	C13—C8—C9—C10	0.0 (3)
C14—C3—C4—C5	−179.06 (17)	C7—C8—C9—C10	−177.21 (16)
C3—C4—C5—C6	−0.5 (2)	C8—C9—C10—C11	−0.1 (3)
C4—C5—C6—C1	−1.0 (2)	C9—C10—C11—C12	−0.1 (4)
C4—C5—C6—S1	179.82 (11)	C10—C11—C12—C13	0.3 (4)
C2—C1—C6—C5	1.7 (2)	C11—C12—C13—C8	−0.3 (3)
C2—C1—C6—S1	−179.11 (12)	C9—C8—C13—C12	0.1 (3)
O2—S1—C6—C5	−1.28 (14)	C7—C8—C13—C12	177.28 (18)
O1—S1—C6—C5	130.48 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.863 (19)	2.082 (19)	2.9446 (17)	177.0 (18)
C5—H5A···O2	0.93	2.54	2.9133 (18)	104

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O₂S
M_r	274.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	5.9593 (7), 9.6592 (7), 23.712 (3)
β (°)	91.533 (9)
V (Å³)	1364.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.50 × 0.40 × 0.03

Data collection
Diffractometer	STOE IPDSII diffractometer
Absorption correction	Numerical (X-SHAPE; Stoe & Cie, 2004)
T_min, T_max	0.879, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	8939, 3573, 3008
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.110, 1.10
No. of reflections	3573
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.25

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek,2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.863 (19)	2.082 (19)	2.9446 (17)	177.0 (18)
C5—H5A···O2	0.9300	2.5400	2.9133 (18)	104.00

Symmetry code: (i) −x+1, −y, −z.

Footnotes

‡Additional correspondance author: e-mail: zsrkk@yahoo.com.

Acknowledgements

HM thanks Vali-e-Asr University of Rafsanjan for the financial support of this work. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HM thanks Professor H.-K. Fun for helpful comments.

References

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