1-Benzoyl-3-(2,4,5-trichloro­phen­yl)thio­urea

Rauf, M.; Ebihara, M.; Badshah, A.; Imtiaz-ud-Din

doi:10.1107/S1600536811052780

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o119

doi:10.1107/S1600536811052780

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1-Benzoyl-3-(2,4,5-trichlorophenyl)thiourea

M. Khawar Rauf,^a ^* Masahiro Ebihara,^b Amin Badshah ^a and Imtiaz-ud-Din ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Faculty of Engineering, Gifu University Yanagido, Gifu 501-1193, Japan
^*Correspondence e-mail: khawar_rauf@hotmail.com

(Received 2 December 2011; accepted 7 December 2011; online 14 December 2011)

The benzene and phenyl rings in the title compound, C₁₄H₉Cl₃N₂OS, form a dihedral angle of 40.98 (6)°. The molecule exists in the thione form with typical thiourea C—S [1.666 (2) Å] and C—O [1.227 (3) Å] bond lengths as well as shortened C—N bonds [1.345 (3) and 1.386 (2) Å]. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation. In the crystal, pairs of N—H⋯S hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For information on thiourea derivatives, see: Patil & Chedekel (1984 ); Baily et al. (1996 ); Namgun et al. (2001 ); Koch (2001 ); Wegner et al. (1986 ); Krishnamurthy et al. (1999 ); Murtaza et al. (2009a ,b ). For related structures, see: Khawar Rauf et al. (2009a ,b ). For bond-length data, see: Allen et al. (1987 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₄H₉Cl₃N₂OS
M_r = 359.64
Monoclinic, C 2/c
a = 33.111 (8) Å
b = 3.8413 (7) Å
c = 25.220 (6) Å
β = 115.995 (2)°
V = 2883.1 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.78 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Rigaku, 1998 ) T_min = 0.800, T_max = 1.000
11264 measured reflections
3264 independent reflections
2686 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.084
S = 1.06
3264 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.89	2.586 (2)	137
N2—H2⋯S1ⁱ	0.86	2.83	3.6771 (19)	168
Symmetry code: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Molecular Structure Corporation and Rigaku, 2001 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPII (Johnson, 1976 ) and TEXSAN (Molecular Structure Corporation and Rigaku, 2004 ); software used to prepare material for publication: Yadokari-XG_2009 (Kabuto et al., 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811052780/bg2439sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052780/bg2439Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052780/bg2439Isup3.cml

checkCIF report

Comment top

Thiourea derivatives are very useful building blocks for the synthesis of a wide range of aliphatic macromolecular and heterocyclic compounds. Thus, benzothiazoles have been prepared from arylthioureas in the presence of bromine (Patil & Chedekel, 1984), 2-aminothiazoles from the condensation of thiourea with α-halocarbonyl compounds (Baily et al., 1996), and 2-Methyl-aminothiazolines from N-(2-hydroxyethyl)-N'-methylthioureas (Namgun et al., 2001). N, N-dialkyl-N-aroylthioureas have been efficiently used for the extraction of Nickle, Palladium and Platinum metals (Koch, 2001). Aliphatic and acylthioureas are well known for their antimicrobial activities (Wegner et al., 1986). Symmetrical and unsymmetrical thioureas have shown antifungal activity against the plant pathogens (Krishnamurthy et al., 1999). We became interested in the synthesis of these thioureas as intermediates in the synthesis of novel guanidines(Murtaza et al., 2009a ; 2009b) and heterocyclic compounds for the systematic study of bioactivity and Complexation behaviour. Hence, we present here the crystal structure of the title compound, (I), Fig. 1. Comparison with N-benzoyl-N'-phenylthioureas [Cambridge Structural Database (Mogul Version 1.7; Allen, 2002) and (Allen et al., 1987)], show the molecule to exist in the thione form with typical thiourea C—S and C—O bonds, as well as shortened C—N bond lengths. Comparison with N-benzoyl-N'-phenylthioureas (Khawar Rauf et al., 2009a,b) suggests the 2,4,5-trichloro substitution on phenyl ring implies no significant effect on these bond lengths. Compound (I) (Fig. 1) shows the typical Thiourea C═S and C═O double bonds as well as shortened C—N bond lengths. The thiocarbonyl and carbonyl groups are almost coplanar, as reflected by the torsion angles C1—N2—C2—O1 [-5.0 (3)] and N1—C1—N2—C2 [1.7 (3)]. This is associated with the expected typical thiourea intramolecular N—H···O H–bond (Table 1), forming a six-membered ring commonly observed in this class of compounds (Khawar Rauf et al., 2009a,b). The dihedral angles to the N1 C1 S1 N2 C2 O1 plane are 50.97 (4)° for the ring formed by C3 to C8 and 11.44 (7)° for the ring formed by C9 to C14. The crystal packing shows intramolecular N—H···O and intermolecular N—H···S H–bonds (Table 1, Fig. 2). The Cl atoms are not involved in any type of H–bonds.

Related literature top

For information on thiourea derivatives, see: Patil & Chedekel (1984); Baily et al. (1996); Namgun et al. (2001); Koch (2001); Wegner et al. (1986); Krishnamurthy et al. (1999); Murtaza et al. (2009a,b). For related structures, see: Khawar Rauf et al. (2009a,b). For bond-length data, see: Allen et al. (1987). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

Freshly prepared benzoylisothiocyanate (1.63 g, 10 mmol) was dissolved in acetone (50 ml) and stirred for 45 minutes. Afterwards neat 2,4,5-trichloroaniline(1.96 g, 10 mmol) was added and the resulting mixture was stirred for 1 h. The reaction mixture was then poured into acidified water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol/1,1-dichloromethane (1:1 v/v) to give fine crystals of the title compound (I), with an overall yield of 95%. Full spectroscopic and physical characterization will be reported elsewhere.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation and Rigaku, 2001); cell refinement: CrystalClear (Molecular Structure Corporation and Rigaku, 2001); data reduction: CrystalClear (Molecular Structure Corporation and Rigaku, 2001); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and TEXSAN (Molecular Structure Corporation and Rigaku, 2004); software used to prepare material for publication: Yadokari-XG_2009 (Kabuto et al., 2009).

Figures top

	Fig. 1. Molecular diagram of (I). Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds shown as dashed lines.
	Fig. 2. Packing diagram of (I) viewed along b-axis. Hydrogen bonds shown as dashed lines.

1-Benzoyl-3-(2,4,5-trichlorophenyl)thiourea top

Crystal data top

C₁₄H₉Cl₃N₂OS	F(000) = 1456
M_r = 359.64	D_x = 1.657 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 3588 reflections
a = 33.111 (8) Å	θ = 3.4–27.5°
b = 3.8413 (7) Å	µ = 0.78 mm⁻¹
c = 25.220 (6) Å	T = 296 K
β = 115.995 (2)°	Prism, colorless
V = 2883.1 (11) Å³	0.20 × 0.20 × 0.20 mm
Z = 8

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3264 independent reflections
Radiation source: Sealed Tube	2686 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.039
Detector resolution: 14.6306 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
dtprofit.ref scans	h = −42→31
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	k = −3→4
T_min = 0.800, T_max = 1.000	l = −28→32
11264 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0345P)² + 0.4746P] where P = (F_o² + 2F_c²)/3
3264 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₄H₉Cl₃N₂OS	V = 2883.1 (11) Å³
M_r = 359.64	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 33.111 (8) Å	µ = 0.78 mm⁻¹
b = 3.8413 (7) Å	T = 296 K
c = 25.220 (6) Å	0.20 × 0.20 × 0.20 mm
β = 115.995 (2)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3264 independent reflections
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	2686 reflections with I > 2σ(I)
T_min = 0.800, T_max = 1.000	R_int = 0.039
11264 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.06	Δρ_max = 0.42 e Å⁻³
3264 reflections	Δρ_min = −0.39 e Å⁻³
190 parameters

Special details top

Experimental. ????

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
C1	0.43321 (7)	0.2438 (4)	0.27137 (9)	0.0156 (4)
S1	0.435250 (18)	0.44890 (12)	0.21438 (2)	0.01721 (13)
N1	0.39554 (6)	0.1658 (4)	0.27661 (7)	0.0169 (4)
H1	0.3985	0.0785	0.3095	0.020*
N2	0.47294 (6)	0.1480 (4)	0.31893 (7)	0.0161 (4)
H2	0.4973	0.2018	0.3166	0.019*
C2	0.47806 (7)	−0.0243 (5)	0.36979 (9)	0.0183 (4)
O1	0.44567 (5)	−0.0919 (4)	0.37941 (7)	0.0262 (4)
C3	0.35153 (7)	0.2166 (5)	0.23204 (9)	0.0159 (4)
C4	0.31883 (7)	0.3736 (5)	0.24474 (9)	0.0169 (4)
C5	0.27552 (7)	0.4225 (4)	0.20171 (10)	0.0183 (5)
H5	0.2542	0.5274	0.2110	0.022*
C6	0.26409 (7)	0.3141 (5)	0.14447 (9)	0.0175 (4)
C7	0.29612 (7)	0.1512 (5)	0.13109 (9)	0.0170 (4)
C8	0.33904 (7)	0.0996 (4)	0.17480 (9)	0.0157 (4)
H8	0.3600	−0.0154	0.1658	0.019*
Cl1	0.332696 (18)	0.51597 (12)	0.31608 (2)	0.02171 (14)
Cl2	0.210441 (17)	0.39364 (12)	0.09054 (2)	0.02358 (14)
Cl3	0.283000 (19)	0.00640 (12)	0.06075 (2)	0.02230 (14)
C9	0.52450 (7)	−0.1244 (4)	0.41257 (9)	0.0160 (4)
C10	0.56177 (7)	−0.1060 (5)	0.40132 (10)	0.0202 (5)
H10	0.5589	−0.0209	0.3653	0.024*
C11	0.60327 (7)	−0.2139 (5)	0.44354 (10)	0.0262 (5)
H11	0.6282	−0.2027	0.4356	0.031*
C12	0.60807 (7)	−0.3382 (5)	0.49742 (10)	0.0236 (5)
H12	0.6361	−0.4100	0.5257	0.028*
C13	0.57106 (8)	−0.3556 (5)	0.50921 (10)	0.0278 (5)
H13	0.5741	−0.4375	0.5455	0.033*
C14	0.52959 (8)	−0.2506 (5)	0.46687 (10)	0.0250 (5)
H14	0.5047	−0.2644	0.4747	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0159 (11)	0.0153 (9)	0.0139 (11)	0.0006 (7)	0.0050 (9)	−0.0028 (7)
S1	0.0155 (3)	0.0206 (2)	0.0151 (3)	0.00181 (18)	0.0063 (2)	0.00292 (18)
N1	0.0143 (9)	0.0239 (8)	0.0117 (9)	0.0017 (6)	0.0048 (8)	0.0036 (7)
N2	0.0117 (9)	0.0228 (8)	0.0127 (9)	0.0001 (6)	0.0042 (8)	0.0017 (6)
C2	0.0181 (12)	0.0218 (10)	0.0136 (11)	0.0013 (8)	0.0058 (10)	0.0001 (8)
O1	0.0157 (9)	0.0441 (9)	0.0203 (9)	0.0027 (6)	0.0093 (8)	0.0103 (7)
C3	0.0135 (11)	0.0174 (9)	0.0143 (11)	−0.0006 (7)	0.0037 (9)	0.0029 (7)
C4	0.0176 (12)	0.0175 (9)	0.0162 (11)	−0.0011 (7)	0.0080 (10)	0.0005 (7)
C5	0.0143 (11)	0.0184 (9)	0.0237 (13)	0.0005 (7)	0.0096 (10)	0.0022 (8)
C6	0.0108 (11)	0.0175 (9)	0.0201 (12)	−0.0010 (7)	0.0031 (9)	0.0052 (8)
C7	0.0180 (11)	0.0170 (9)	0.0142 (11)	−0.0017 (7)	0.0054 (9)	0.0007 (7)
C8	0.0143 (11)	0.0161 (9)	0.0174 (11)	0.0009 (7)	0.0076 (9)	0.0011 (8)
Cl1	0.0205 (3)	0.0287 (3)	0.0170 (3)	0.00048 (19)	0.0092 (2)	−0.00330 (19)
Cl2	0.0140 (3)	0.0281 (3)	0.0231 (3)	0.00175 (19)	0.0030 (2)	0.0041 (2)
Cl3	0.0202 (3)	0.0295 (3)	0.0133 (3)	−0.00027 (19)	0.0038 (2)	−0.00146 (19)
C9	0.0144 (11)	0.0167 (9)	0.0138 (11)	0.0013 (7)	0.0033 (9)	−0.0008 (7)
C10	0.0217 (12)	0.0211 (10)	0.0182 (12)	0.0011 (8)	0.0091 (10)	0.0033 (8)
C11	0.0178 (12)	0.0298 (11)	0.0301 (14)	0.0022 (9)	0.0097 (11)	0.0056 (9)
C12	0.0176 (12)	0.0218 (10)	0.0213 (13)	0.0016 (8)	−0.0007 (10)	0.0033 (8)
C13	0.0291 (14)	0.0337 (12)	0.0168 (13)	0.0025 (9)	0.0066 (11)	0.0055 (9)
C14	0.0193 (13)	0.0349 (11)	0.0214 (13)	0.0032 (9)	0.0093 (11)	0.0054 (9)

Geometric parameters (Å, º) top

C1—N1	1.345 (3)	C6—Cl2	1.727 (2)
C1—N2	1.386 (2)	C7—C8	1.379 (3)
C1—S1	1.666 (2)	C7—Cl3	1.723 (2)
N1—C3	1.410 (2)	C8—H8	0.9300
N1—H1	0.8600	C9—C10	1.384 (3)
N2—C2	1.386 (3)	C9—C14	1.391 (3)
N2—H2	0.8600	C10—C11	1.382 (3)
C2—O1	1.227 (3)	C10—H10	0.9300
C2—C9	1.491 (3)	C11—C12	1.382 (3)
C3—C8	1.391 (3)	C11—H11	0.9300
C3—C4	1.394 (3)	C12—C13	1.383 (3)
C4—C5	1.380 (3)	C12—H12	0.9300
C4—Cl1	1.739 (2)	C13—C14	1.379 (3)
C5—C6	1.386 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.394 (3)

N1—C1—N2	115.16 (18)	C8—C7—C6	119.9 (2)
N1—C1—S1	125.47 (16)	C8—C7—Cl3	118.89 (16)
N2—C1—S1	119.36 (15)	C6—C7—Cl3	121.24 (17)
C1—N1—C3	124.74 (18)	C7—C8—C3	121.12 (19)
C1—N1—H1	117.6	C7—C8—H8	119.4
C3—N1—H1	117.6	C3—C8—H8	119.4
C2—N2—C1	127.76 (18)	C10—C9—C14	119.02 (19)
C2—N2—H2	116.1	C10—C9—C2	124.6 (2)
C1—N2—H2	116.1	C14—C9—C2	116.36 (19)
O1—C2—N2	121.4 (2)	C11—C10—C9	120.1 (2)
O1—C2—C9	121.06 (19)	C11—C10—H10	119.9
N2—C2—C9	117.51 (18)	C9—C10—H10	119.9
C8—C3—C4	118.10 (19)	C12—C11—C10	120.5 (2)
C8—C3—N1	121.05 (18)	C12—C11—H11	119.7
C4—C3—N1	120.81 (19)	C10—C11—H11	119.7
C5—C4—C3	121.5 (2)	C11—C12—C13	119.8 (2)
C5—C4—Cl1	118.90 (16)	C11—C12—H12	120.1
C3—C4—Cl1	119.63 (16)	C13—C12—H12	120.1
C4—C5—C6	119.57 (19)	C14—C13—C12	119.6 (2)
C4—C5—H5	120.2	C14—C13—H13	120.2
C6—C5—H5	120.2	C12—C13—H13	120.2
C5—C6—C7	119.82 (19)	C13—C14—C9	120.9 (2)
C5—C6—Cl2	118.96 (16)	C13—C14—H14	119.5
C7—C6—Cl2	121.20 (17)	C9—C14—H14	119.5

N2—C1—N1—C3	−175.25 (16)	C5—C6—C7—Cl3	178.95 (14)
S1—C1—N1—C3	6.3 (3)	Cl2—C6—C7—Cl3	−2.6 (2)
N1—C1—N2—C2	1.7 (3)	C6—C7—C8—C3	−1.9 (3)
S1—C1—N2—C2	−179.68 (15)	Cl3—C7—C8—C3	178.94 (14)
C1—N2—C2—O1	−5.0 (3)	C4—C3—C8—C7	2.9 (3)
C1—N2—C2—C9	175.03 (17)	N1—C3—C8—C7	−179.55 (16)
C1—N1—C3—C8	49.5 (3)	O1—C2—C9—C10	169.75 (18)
C1—N1—C3—C4	−133.0 (2)	N2—C2—C9—C10	−10.3 (3)
C8—C3—C4—C5	−1.9 (3)	O1—C2—C9—C14	−9.0 (3)
N1—C3—C4—C5	−179.45 (17)	N2—C2—C9—C14	170.96 (17)
C8—C3—C4—Cl1	178.74 (14)	C14—C9—C10—C11	0.4 (3)
N1—C3—C4—Cl1	1.2 (2)	C2—C9—C10—C11	−178.33 (18)
C3—C4—C5—C6	−0.1 (3)	C9—C10—C11—C12	−0.5 (3)
Cl1—C4—C5—C6	179.25 (14)	C10—C11—C12—C13	0.1 (3)
C4—C5—C6—C7	1.2 (3)	C11—C12—C13—C14	0.4 (3)
C4—C5—C6—Cl2	−177.30 (14)	C12—C13—C14—C9	−0.6 (3)
C5—C6—C7—C8	−0.2 (3)	C10—C9—C14—C13	0.2 (3)
Cl2—C6—C7—C8	178.26 (14)	C2—C9—C14—C13	178.98 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.89	2.586 (2)	137
N2—H2···S1ⁱ	0.86	2.83	3.6771 (19)	168

Symmetry code: (i) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₉Cl₃N₂OS
M_r	359.64
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	33.111 (8), 3.8413 (7), 25.220 (6)
β (°)	115.995 (2)
V (Å³)	2883.1 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.78
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku/MSC Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB; Rigaku, 1998)
T_min, T_max	0.800, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11264, 3264, 2686
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.084, 1.06
No. of reflections	3264
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.39

Computer programs: CrystalClear (Molecular Structure Corporation and Rigaku, 2001), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and TEXSAN (Molecular Structure Corporation and Rigaku, 2004), Yadokari-XG_2009 (Kabuto et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.89	2.586 (2)	137.2
N2—H2···S1ⁱ	0.86	2.83	3.6771 (19)	167.5

Symmetry code: (i) −x+1, y, −z+1/2.

Acknowledgements

MKR is grateful to the Quaid-i-Azam University, Islamabad, for financial support for a post-doctoral fellowship.

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