2-(2,4-Dichloro­phen­oxy­meth­yl)-5-(4-methyl­phen­yl)imidazo[2,1-b][1,3,4]thia­diazole

Abdel-Wahab, B.F.; Mohamed, H.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S160053681300384X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o377

doi:10.1107/S160053681300384X

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2-(2,4-Dichlorophenoxymethyl)-5-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole †

Bakr F. Abdel-Wahab,^a Hanan A. Mohamed,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 8 February 2013; accepted 8 February 2013; online 13 February 2013)

In the title compound, C₁₈H₁₃Cl₂N₃OS, the eight atoms comprising the central imidazo/thiadiazolethiadiazole residue are coplanar (r.m.s. deviation = 0.009 Å). The dihedral angle of 8.72 (13)° between the dichlorobenzene and tolyl rings reflects a twist about the O—C(benzene) bond; the C_m—O—C_b—C_b torsion angle = −168.5 (2)° (m = methylene C and b is benzene C). Supramolecular tapes along the b axis are found in the crystal structure which are mediated by π–π interactions occurring between centrosymmetrically related thiadiazole rings [inter-ring centroid distance = 3.6907 (16) Å] and between the benzene and tolyl rings [inter-ring centroid distance = 3.7597 (16) Å].

Related literature

For background to the biological activity of imidazothiadiazoles, see: Abdel-Wahab et al. (2011 ); Karki et al. (2011 ); Khazi et al. (2011 ). For the synthesis, see: Abdel-Wahab et al. (2011). For a related structure, see: Fun et al. (2011 ).

Experimental

Crystal data

C₁₈H₁₃Cl₂N₃OS
M_r = 390.27
Triclinic, $[P \overline 1]$
a = 8.3015 (7) Å
b = 8.3053 (7) Å
c = 14.4374 (13) Å
α = 97.180 (7)°
β = 92.644 (7)°
γ = 118.996 (9)°
V = 857.25 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 295 K
0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.856, T_max = 1.000
8391 measured reflections
3932 independent reflections
2659 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.172
S = 0.98
3932 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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/S160053681300384X/hg5290sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681300384X/hg5290Isup2.hkl

checkCIF report

Comment top

The title compound (I) was investigated in relation to the established biological activities exhibited by imidazothiadiazoles (Abdel-Wahab et al., 2011; Karki et al., 2011; Khazi et al., 2011).

In (I), Fig. 1, the eight atoms comprising the fused imidazo/thiadiazolethiadiazole residue are co-planar (r.m.s. deviation = 0.009 Å). This system forms dihedral angles of 6.01 (10) and 3.28 (11)° with the attached dichlorobenzene and tolyl rings, respectively. The r.m.s. deviation from the least-squares plane for all 25 non-hydrogen atoms is 0.085 Å with maximum deviations of 0.180 (2) and -0.197 (1) for the O1 and Cl1 atoms, respectively. This is consistent with a small twist about the C1—O1 bond with the C7—O1—C1—C2 torsion angle being -168.5 (2)°. The S and O atoms are syn and are separated by 2.823 (3) Å. A small twist was also observed in the structure of the closely related compound 2-isobutyl-6-phenylimidazo[2,1-b][1,3,4]thiadiazole (Fun et al., 2011).

In the crystal packing, molecules aggregate into tapes along the b axis via π–π interactions occurring between centrosymmetrically related thiadiazole rings [inter-ring centroid distance = 3.6907 (16) Å for symmetry operation: 2 - x, -y, 1 - z] and between the benzene and tolyl rings [inter-ring centroid distance = 3.7597 (16) Å for symmetry operation: 2 - x, 1 - y, 1 - z], Fig. 2. Columns stack with no specific interactions between them, Fig. 3.

Related literature top

For background to the biological activity of imidazothiadiazoles, see: Abdel-Wahab et al. (2011); Karki et al. (2011); Khazi et al. (2011). For the synthesis, see: Abdel-Wahab et al. (2011). For a related structure, see: Fun et al. (2011).

Experimental top

The title compound was prepared according to the reported method (Abdel-Wahab et al., 2011). Colourless crystals were obtained from DMF solution by slow evaporation at room temperature.

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 (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular tape along the b axis in (I) mediated by π—π interactions shown as purple dashed lines.
	Fig. 3. A view of the crystal packing in projection down the b axis. The π—π interactions are shown as purple dashed lines.

2-(2,4-Dichlorophenoxymethyl)-5-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole top

Crystal data top

C₁₈H₁₃Cl₂N₃OS	Z = 2
M_r = 390.27	F(000) = 400
Triclinic, P1	D_x = 1.512 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3015 (7) Å	Cell parameters from 1915 reflections
b = 8.3053 (7) Å	θ = 2.8–27.5°
c = 14.4374 (13) Å	µ = 0.51 mm⁻¹
α = 97.180 (7)°	T = 295 K
β = 92.644 (7)°	Prism, colourless
γ = 118.996 (9)°	0.40 × 0.30 × 0.20 mm
V = 857.25 (13) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3932 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2659 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.8°
ω scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→10
T_min = 0.856, T_max = 1.000	l = −18→15
8391 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3932 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₈H₁₃Cl₂N₃OS	γ = 118.996 (9)°
M_r = 390.27	V = 857.25 (13) Å³
Triclinic, P1	Z = 2
a = 8.3015 (7) Å	Mo Kα radiation
b = 8.3053 (7) Å	µ = 0.51 mm⁻¹
c = 14.4374 (13) Å	T = 295 K
α = 97.180 (7)°	0.40 × 0.30 × 0.20 mm
β = 92.644 (7)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3932 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2659 reflections with I > 2σ(I)
T_min = 0.856, T_max = 1.000	R_int = 0.028
8391 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.172	H-atom parameters constrained
S = 0.98	Δρ_max = 0.27 e Å⁻³
3932 reflections	Δρ_min = −0.24 e Å⁻³
227 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
Cl1	0.83905 (10)	0.40968 (12)	0.15939 (6)	0.0701 (3)
Cl2	0.16453 (12)	0.30193 (13)	0.04111 (6)	0.0730 (3)
S1	1.00105 (10)	0.30491 (9)	0.41463 (5)	0.0493 (2)
O1	0.6883 (3)	0.3049 (3)	0.32904 (14)	0.0540 (5)
C1	0.5593 (3)	0.3020 (3)	0.26664 (19)	0.0429 (6)
C2	0.6151 (4)	0.3510 (3)	0.1799 (2)	0.0462 (6)
C3	0.4962 (4)	0.3525 (3)	0.1110 (2)	0.0494 (6)
H3	0.5354	0.3847	0.0534	0.059*
C4	0.3174 (4)	0.3053 (3)	0.12837 (19)	0.0476 (6)
C5	0.2607 (4)	0.2588 (4)	0.2137 (2)	0.0522 (7)
H5	0.1408	0.2286	0.2252	0.063*
C6	0.3797 (4)	0.2565 (4)	0.2827 (2)	0.0497 (6)
H6	0.3396	0.2244	0.3402	0.060*
C7	0.6268 (4)	0.2235 (4)	0.40983 (19)	0.0492 (6)
H7A	0.5252	0.0964	0.3920	0.059*
H7B	0.5844	0.2946	0.4497	0.059*
C8	0.7883 (4)	0.2255 (3)	0.46024 (18)	0.0431 (6)
C9	1.0864 (4)	0.2605 (3)	0.51522 (18)	0.0444 (6)
C10	1.0183 (4)	0.1610 (4)	0.6497 (2)	0.0506 (6)
H10	0.9573	0.1154	0.7009	0.061*
C11	1.1978 (4)	0.2117 (3)	0.63753 (18)	0.0444 (6)
C12	1.3346 (4)	0.2063 (3)	0.70303 (19)	0.0455 (6)
C13	1.5166 (4)	0.2710 (4)	0.6864 (2)	0.0538 (7)
H13	1.5549	0.3204	0.6319	0.065*
C14	1.6426 (4)	0.2638 (4)	0.7489 (2)	0.0584 (7)
H14	1.7644	0.3099	0.7358	0.070*
C15	1.5936 (4)	0.1901 (4)	0.8307 (2)	0.0541 (7)
C16	1.4112 (5)	0.1263 (4)	0.8480 (2)	0.0650 (8)
H16	1.3732	0.0769	0.9025	0.078*
C17	1.2846 (4)	0.1347 (4)	0.7856 (2)	0.0607 (8)
H17	1.1635	0.0915	0.7993	0.073*
C18	1.7309 (5)	0.1820 (4)	0.8983 (2)	0.0712 (9)
H18A	1.8126	0.1532	0.8640	0.107*
H18B	1.6661	0.0869	0.9355	0.107*
H18C	1.8019	0.3006	0.9389	0.107*
N1	0.7783 (3)	0.1707 (3)	0.54018 (17)	0.0506 (5)
N2	0.9469 (3)	0.1916 (3)	0.57041 (15)	0.0448 (5)
N3	1.2402 (3)	0.2741 (3)	0.55163 (15)	0.0483 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0431 (4)	0.1083 (6)	0.0602 (5)	0.0340 (4)	0.0157 (4)	0.0301 (4)
Cl2	0.0630 (5)	0.1060 (6)	0.0645 (5)	0.0519 (5)	−0.0016 (4)	0.0230 (5)
S1	0.0468 (4)	0.0648 (4)	0.0379 (4)	0.0278 (3)	0.0067 (3)	0.0129 (3)
O1	0.0417 (10)	0.0749 (11)	0.0495 (12)	0.0280 (9)	0.0083 (9)	0.0273 (9)
C1	0.0371 (13)	0.0467 (12)	0.0439 (15)	0.0189 (11)	0.0054 (11)	0.0120 (11)
C2	0.0374 (14)	0.0519 (13)	0.0486 (16)	0.0202 (12)	0.0068 (12)	0.0136 (12)
C3	0.0496 (16)	0.0583 (15)	0.0438 (16)	0.0277 (14)	0.0094 (13)	0.0153 (12)
C4	0.0454 (15)	0.0534 (13)	0.0480 (16)	0.0273 (12)	0.0015 (12)	0.0108 (12)
C5	0.0411 (15)	0.0637 (15)	0.0578 (18)	0.0289 (13)	0.0095 (14)	0.0165 (14)
C6	0.0447 (15)	0.0623 (15)	0.0467 (16)	0.0275 (13)	0.0112 (13)	0.0174 (13)
C7	0.0462 (15)	0.0559 (14)	0.0464 (16)	0.0244 (13)	0.0061 (13)	0.0155 (12)
C8	0.0450 (14)	0.0421 (12)	0.0401 (15)	0.0201 (11)	0.0035 (12)	0.0070 (11)
C9	0.0441 (14)	0.0473 (13)	0.0389 (15)	0.0212 (12)	0.0047 (12)	0.0047 (11)
C10	0.0479 (16)	0.0593 (14)	0.0470 (16)	0.0263 (13)	0.0054 (13)	0.0188 (13)
C11	0.0471 (15)	0.0400 (12)	0.0432 (15)	0.0208 (11)	−0.0017 (12)	0.0039 (11)
C12	0.0445 (15)	0.0424 (12)	0.0434 (15)	0.0193 (12)	−0.0055 (12)	−0.0001 (11)
C13	0.0531 (17)	0.0679 (16)	0.0442 (16)	0.0328 (14)	0.0044 (13)	0.0102 (13)
C14	0.0512 (17)	0.0751 (18)	0.0528 (18)	0.0372 (15)	−0.0016 (14)	0.0013 (15)
C15	0.0609 (19)	0.0463 (14)	0.0535 (18)	0.0282 (14)	−0.0088 (14)	0.0016 (12)
C16	0.066 (2)	0.0637 (17)	0.0558 (19)	0.0232 (16)	−0.0040 (16)	0.0218 (15)
C17	0.0493 (17)	0.0652 (17)	0.0586 (19)	0.0193 (14)	0.0005 (15)	0.0217 (15)
C18	0.072 (2)	0.0674 (17)	0.075 (2)	0.0387 (17)	−0.0184 (18)	0.0059 (17)
N1	0.0425 (13)	0.0618 (12)	0.0509 (14)	0.0255 (11)	0.0078 (11)	0.0217 (11)
N2	0.0397 (12)	0.0514 (11)	0.0443 (13)	0.0218 (10)	0.0059 (10)	0.0141 (10)
N3	0.0427 (12)	0.0599 (12)	0.0424 (13)	0.0252 (11)	0.0050 (10)	0.0107 (10)

Geometric parameters (Å, º) top

Cl1—C2	1.729 (3)	C10—C11	1.365 (4)
Cl2—C4	1.734 (3)	C10—N2	1.373 (3)
S1—C9	1.743 (3)	C10—H10	0.9300
S1—C8	1.753 (3)	C11—N3	1.398 (3)
O1—C1	1.356 (3)	C11—C12	1.465 (4)
O1—C7	1.413 (3)	C12—C13	1.381 (4)
C1—C6	1.388 (4)	C12—C17	1.390 (4)
C1—C2	1.395 (4)	C13—C14	1.379 (4)
C2—C3	1.374 (4)	C13—H13	0.9300
C3—C4	1.384 (4)	C14—C15	1.384 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.373 (4)	C15—C16	1.388 (4)
C5—C6	1.378 (4)	C15—C18	1.499 (4)
C5—H5	0.9300	C16—C17	1.386 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.487 (4)	C17—H17	0.9300
C7—H7A	0.9700	C18—H18A	0.9600
C7—H7B	0.9700	C18—H18B	0.9600
C8—N1	1.284 (3)	C18—H18C	0.9600
C9—N3	1.305 (3)	N1—N2	1.367 (3)
C9—N2	1.364 (3)

C9—S1—C8	88.01 (12)	N2—C10—H10	127.3
C1—O1—C7	117.4 (2)	C10—C11—N3	110.8 (2)
O1—C1—C6	125.4 (2)	C10—C11—C12	126.9 (3)
O1—C1—C2	116.3 (2)	N3—C11—C12	122.2 (2)
C6—C1—C2	118.3 (3)	C13—C12—C17	117.1 (3)
C3—C2—C1	121.5 (2)	C13—C12—C11	122.4 (3)
C3—C2—Cl1	119.7 (2)	C17—C12—C11	120.5 (2)
C1—C2—Cl1	118.7 (2)	C14—C13—C12	121.3 (3)
C2—C3—C4	119.2 (3)	C14—C13—H13	119.3
C2—C3—H3	120.4	C12—C13—H13	119.3
C4—C3—H3	120.4	C13—C14—C15	122.0 (3)
C5—C4—C3	120.1 (3)	C13—C14—H14	119.0
C5—C4—Cl2	120.3 (2)	C15—C14—H14	119.0
C3—C4—Cl2	119.6 (2)	C14—C15—C16	116.8 (3)
C4—C5—C6	120.7 (2)	C14—C15—C18	121.9 (3)
C4—C5—H5	119.6	C16—C15—C18	121.3 (3)
C6—C5—H5	119.6	C17—C16—C15	121.2 (3)
C5—C6—C1	120.2 (3)	C17—C16—H16	119.4
C5—C6—H6	119.9	C15—C16—H16	119.4
C1—C6—H6	119.9	C16—C17—C12	121.5 (3)
O1—C7—C8	106.6 (2)	C16—C17—H17	119.3
O1—C7—H7A	110.4	C12—C17—H17	119.3
C8—C7—H7A	110.4	C15—C18—H18A	109.5
O1—C7—H7B	110.4	C15—C18—H18B	109.5
C8—C7—H7B	110.4	H18A—C18—H18B	109.5
H7A—C7—H7B	108.6	C15—C18—H18C	109.5
N1—C8—C7	121.1 (2)	H18A—C18—H18C	109.5
N1—C8—S1	116.9 (2)	H18B—C18—H18C	109.5
C7—C8—S1	121.93 (19)	C8—N1—N2	108.3 (2)
N3—C9—N2	113.1 (2)	C9—N2—N1	118.9 (2)
N3—C9—S1	139.0 (2)	C9—N2—C10	106.8 (2)
N2—C9—S1	107.86 (19)	N1—N2—C10	134.3 (2)
C11—C10—N2	105.4 (2)	C9—N3—C11	103.8 (2)
C11—C10—H10	127.3

C7—O1—C1—C6	12.1 (4)	C10—C11—C12—C17	3.8 (4)
C7—O1—C1—C2	−168.5 (2)	N3—C11—C12—C17	−176.8 (2)
O1—C1—C2—C3	179.8 (2)	C17—C12—C13—C14	0.3 (4)
C6—C1—C2—C3	−0.8 (4)	C11—C12—C13—C14	−179.7 (2)
O1—C1—C2—Cl1	0.1 (3)	C12—C13—C14—C15	0.7 (4)
C6—C1—C2—Cl1	179.52 (18)	C13—C14—C15—C16	−1.2 (4)
C1—C2—C3—C4	0.4 (4)	C13—C14—C15—C18	179.8 (3)
Cl1—C2—C3—C4	−179.96 (18)	C14—C15—C16—C17	0.6 (4)
C2—C3—C4—C5	0.4 (4)	C18—C15—C16—C17	179.7 (3)
C2—C3—C4—Cl2	−178.67 (19)	C15—C16—C17—C12	0.4 (4)
C3—C4—C5—C6	−0.7 (4)	C13—C12—C17—C16	−0.8 (4)
Cl2—C4—C5—C6	178.4 (2)	C11—C12—C17—C16	179.2 (3)
C4—C5—C6—C1	0.2 (4)	C7—C8—N1—N2	−178.7 (2)
O1—C1—C6—C5	179.9 (2)	S1—C8—N1—N2	0.5 (3)
C2—C1—C6—C5	0.5 (4)	N3—C9—N2—N1	179.9 (2)
C1—O1—C7—C8	173.7 (2)	S1—C9—N2—N1	0.0 (3)
O1—C7—C8—N1	175.6 (2)	N3—C9—N2—C10	0.9 (3)
O1—C7—C8—S1	−3.6 (3)	S1—C9—N2—C10	−178.94 (16)
C9—S1—C8—N1	−0.4 (2)	C8—N1—N2—C9	−0.3 (3)
C9—S1—C8—C7	178.8 (2)	C8—N1—N2—C10	178.3 (3)
C8—S1—C9—N3	−179.7 (3)	C11—C10—N2—C9	−0.6 (3)
C8—S1—C9—N2	0.19 (17)	C11—C10—N2—N1	−179.3 (2)
N2—C10—C11—N3	0.1 (3)	N2—C9—N3—C11	−0.8 (3)
N2—C10—C11—C12	179.6 (2)	S1—C9—N3—C11	179.0 (2)
C10—C11—C12—C13	−176.2 (2)	C10—C11—N3—C9	0.4 (3)
N3—C11—C12—C13	3.2 (3)	C12—C11—N3—C9	−179.1 (2)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃Cl₂N₃OS
M_r	390.27
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.3015 (7), 8.3053 (7), 14.4374 (13)
α, β, γ (°)	97.180 (7), 92.644 (7), 118.996 (9)
V (Å³)	857.25 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.856, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8391, 3932, 2659
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.172, 0.98
No. of reflections	3932
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −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).

Footnotes

†Additional correspondence author, e-mail: bakrfatehy@yahoo.com.

Acknowledgements

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).

References

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