Bis(2,4-dinitro­phen­yl)sulfane

Buvaneswari, M.; Kalaivani, D.; Nethaji, M.

doi:10.1107/S1600536812041803

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3116

doi:10.1107/S1600536812041803

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Bis(2,4-dinitrophenyl)sulfane

M Buvaneswari,^a D Kalaivani ^a ^* and M Nethaji ^b

^aPG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India, and ^bDepartment of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560 012, India
^*Correspondence e-mail: kalaivbalaj@yahoo.co.in

(Received 22 September 2012; accepted 5 October 2012; online 13 October 2012)

In the title compound, C₁₂H₆N₄O₈S, the dinitrophenyl rings subtend an angle of 78.46 (13) °. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds leading to the formation of a two-dimensional network lying parallel to the bc plane.

Related literature

For applications of bis(2,4-dinitrophenyl)sulfane, see: Nakadate et al. (1964 ); Alekhina et al. (1978 ); Parihar et al. (1971 ); Evans & Kinnard (1983 ); Andricopulo et al. (2006 ). For related syntheses, see: Pesin et al. (1963 ); Joshi & Mathur (1963 ); Obata et al. (1966 ); Stepanov et al. (1974 ); Davydov & Beletskaya (2003 ). For our previous work to synthesize new substituted barbiturates, see: Manickkam & Kalaivani (2011 ); Rajamani & Kalaivani (2012 ).

Experimental

Crystal data

C₁₂H₆N₄O₈S
M_r = 366.27
Monoclinic, P 2₁ /c
a = 9.9428 (12) Å
b = 7.3693 (9) Å
c = 19.743 (2) Å
β = 95.525 (8)°
V = 1439.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.15 × 0.06 × 0.03 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.958, T_max = 0.991
15342 measured reflections
2949 independent reflections
1651 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.110
S = 0.99
2949 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O8ⁱ	0.93	2.54	3.080 (3)	117
C6—H6⋯O7ⁱⁱ	0.93	2.49	3.364 (3)	156
C11—H11⋯O2ⁱⁱⁱ	0.93	2.57	3.489 (3)	168
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812041803/su2502sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041803/su2502Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812041803/su2502Isup3.cml

checkCIF report

Comment top

The title sulfur containing organic compound is a biologically active molecule (Andricopulo et al., 2006). It has been utilized in many clinical trials (Nakadate et al., 1964; Alekhina et al., 1978) and also employed in the synthesis of a number of other important organic molecules (Parihar et al., 1971; Evans & Kinnard, 1983). Several methods have been reported for the synthesis of the title molecule (Pesin et al., 1963; Joshi & Mathur, 1963; Obata et al., 1966; Stepanov et al., 1974; Davydov & Beletskaya, 2003). In continuation of our previous work to synthesize new substituted barbiturates when 2-thiobarbituric acid is used (Manickkam & Kalaivani, 2011; Rajamani & Kalaivani, 2012) , the title molecule was obtained crystallizing out as the product through a new synthetic route.

In the title molecule (Fig. 1) the two phenyl rings are inclined to one another by 78.46 (13) °.

In the crystal, there are a number of weak C—H···O hydrogen bonds linking the molecules to form a two-dimensional network lying parallel to the bc plane (Table 1 and Fig. 2).

Related literature top

For applications of bis(2,4-dinitrophenyl)sulfane, see: Nakadate et al. (1964); Alekhina et al. (1978); Parihar et al. (1971); Evans & Kinnard (1983); Andricopulo et al. (2006). For related syntheses, see: Pesin et al. (1963); Joshi & Mathur (1963); Obata et al. (1966); Stepanov et al. (1974); Davydov & Beletskaya (2003). For our previous work to synthesize new substituted barbiturates, see: Manickkam & Kalaivani (2011); Rajamani & Kalaivani (2012).

Experimental top

Analytical grade 1-chloro-2,4-dinitrobenzene (2.02 g, 0.01 mol) dissolved in ethanol (20 ml) and 2-thiobarbituricacid (1.44 g, 0.01 mol) dissolved in ethanol (20 ml) were mixed. Triethylamine (5 g,0.05 mol) was then added and the mixture was shaken well for 5–6 hrs. On standing yellow crystals came out from the solution after 5 days. The crystals were filtered and washed well with ether to remove the unreacted reactants and then with a small amount of absolute alcohol. The crystals were recrystallized from ethanol (M.pt: 467 K; yield: 70%). Good quality single crystals for X-ray diffraction studies were obtained by slow evaporation of a solution in ethanol at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. A view of the molecular structure of the title molecule, with the atom numbering. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view along the b axis of the crystal packing of the title compound. The C-H···O hydrogen bonds are shown as dashed cyan lines (H atoms not involved in these interactions have been omitted for clarity; see Table 1 for details).

Bis(2,4-dinitrophenyl)sulfane top

Crystal data top

C₁₂H₆N₄O₈S	F(000) = 744
M_r = 366.27	D_x = 1.690 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 687 reflections
a = 9.9428 (12) Å	θ = 2.5–26.0°
b = 7.3693 (9) Å	µ = 0.28 mm⁻¹
c = 19.743 (2) Å	T = 296 K
β = 95.525 (8)°	Needle, yellow
V = 1439.9 (3) Å³	0.15 × 0.06 × 0.03 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	2949 independent reflections
Radiation source: fine-focus sealed tube	1651 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
ω scans	θ_max = 26.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→12
T_min = 0.958, T_max = 0.991	k = −9→9
15342 measured reflections	l = −24→24

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0462P)²] where P = (F_o² + 2F_c²)/3
2949 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₂H₆N₄O₈S	V = 1439.9 (3) Å³
M_r = 366.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9428 (12) Å	µ = 0.28 mm⁻¹
b = 7.3693 (9) Å	T = 296 K
c = 19.743 (2) Å	0.15 × 0.06 × 0.03 mm
β = 95.525 (8)°

Data collection top

Bruker SMART APEX CCD diffractometer	2949 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1651 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.991	R_int = 0.070
15342 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 0.99	Δρ_max = 0.21 e Å⁻³
2949 reflections	Δρ_min = −0.19 e Å⁻³
226 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
S1	0.45894 (8)	0.54204 (10)	0.14730 (4)	0.0467 (3)
O1	0.3487 (3)	0.3356 (3)	0.26264 (12)	0.0808 (10)
O2	0.4165 (2)	0.4985 (3)	0.35003 (11)	0.0765 (10)
O3	0.0912 (3)	1.0117 (4)	0.35223 (14)	0.0914 (11)
O4	0.0607 (3)	1.1747 (4)	0.26196 (14)	0.0947 (11)
O5	−0.0437 (3)	0.1541 (3)	−0.05028 (11)	0.0740 (10)
O6	0.1255 (3)	0.0405 (4)	−0.09656 (12)	0.0925 (11)
O7	0.5752 (2)	0.1785 (3)	−0.00808 (11)	0.0684 (9)
O8	0.6174 (2)	0.3770 (3)	0.07036 (11)	0.0624 (8)
N1	0.3628 (3)	0.4798 (3)	0.29238 (13)	0.0520 (10)
N2	0.1077 (3)	1.0440 (4)	0.29312 (16)	0.0599 (11)
N3	0.0775 (3)	0.1350 (4)	−0.05396 (13)	0.0611 (10)
N4	0.5382 (3)	0.2847 (3)	0.03373 (12)	0.0459 (9)
C1	0.3436 (3)	0.6771 (3)	0.18964 (13)	0.0367 (9)
C2	0.3140 (3)	0.6456 (3)	0.25585 (13)	0.0368 (9)
C3	0.2394 (3)	0.7630 (4)	0.29087 (13)	0.0423 (10)
C4	0.1913 (3)	0.9165 (4)	0.25738 (14)	0.0401 (10)
C5	0.2169 (3)	0.9557 (4)	0.19209 (14)	0.0449 (10)
C6	0.2941 (3)	0.8364 (4)	0.15892 (13)	0.0440 (10)
C7	0.3467 (3)	0.4152 (3)	0.09096 (12)	0.0371 (9)
C8	0.2065 (3)	0.4231 (3)	0.09266 (13)	0.0441 (10)
C9	0.1189 (3)	0.3318 (4)	0.04641 (14)	0.0477 (10)
C10	0.1710 (3)	0.2295 (4)	−0.00390 (13)	0.0447 (10)
C11	0.3068 (3)	0.2136 (3)	−0.00716 (13)	0.0465 (10)
C12	0.3938 (3)	0.3044 (3)	0.04037 (12)	0.0382 (9)
H3	0.22210	0.73970	0.33550	0.0510*
H5	0.18280	1.06060	0.17070	0.0540*
H6	0.31380	0.86290	0.11490	0.0530*
H8	0.17140	0.49230	0.12620	0.0530*
H9	0.02610	0.33860	0.04880	0.0570*
H11	0.34050	0.14300	−0.04070	0.0560*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0398 (5)	0.0482 (4)	0.0514 (5)	0.0035 (4)	0.0003 (4)	−0.0120 (3)
O1	0.103 (2)	0.0390 (13)	0.0968 (18)	−0.0003 (13)	−0.0090 (15)	0.0069 (12)
O2	0.0911 (19)	0.0906 (18)	0.0463 (14)	0.0343 (15)	−0.0016 (13)	0.0164 (12)
O3	0.099 (2)	0.103 (2)	0.0792 (18)	0.0258 (16)	0.0441 (16)	−0.0093 (15)
O4	0.088 (2)	0.0925 (19)	0.103 (2)	0.0568 (17)	0.0064 (16)	−0.0047 (16)
O5	0.0647 (18)	0.0820 (17)	0.0701 (16)	−0.0079 (15)	−0.0199 (14)	−0.0082 (12)
O6	0.101 (2)	0.0974 (19)	0.0755 (17)	0.0002 (17)	−0.0092 (15)	−0.0459 (15)
O7	0.0732 (17)	0.0770 (15)	0.0579 (14)	0.0166 (13)	0.0215 (12)	−0.0157 (12)
O8	0.0480 (14)	0.0682 (14)	0.0712 (15)	0.0035 (12)	0.0067 (12)	−0.0111 (12)
N1	0.0514 (17)	0.0513 (17)	0.0532 (17)	0.0087 (13)	0.0042 (14)	0.0107 (13)
N2	0.0426 (17)	0.0652 (18)	0.072 (2)	0.0118 (15)	0.0060 (15)	−0.0144 (16)
N3	0.072 (2)	0.0569 (17)	0.0512 (17)	−0.0049 (17)	−0.0103 (17)	−0.0068 (13)
N4	0.0543 (18)	0.0448 (14)	0.0394 (14)	0.0080 (13)	0.0084 (13)	0.0055 (11)
C1	0.0345 (17)	0.0352 (15)	0.0391 (16)	0.0006 (13)	−0.0030 (13)	−0.0044 (12)
C2	0.0331 (17)	0.0365 (14)	0.0396 (16)	−0.0003 (13)	−0.0033 (13)	0.0030 (12)
C3	0.0343 (17)	0.0539 (17)	0.0385 (16)	−0.0014 (14)	0.0031 (13)	−0.0004 (13)
C4	0.0292 (17)	0.0413 (16)	0.0493 (18)	0.0016 (13)	0.0019 (13)	−0.0092 (13)
C5	0.0441 (18)	0.0392 (15)	0.0500 (18)	0.0066 (15)	−0.0022 (14)	0.0027 (14)
C6	0.0494 (19)	0.0464 (16)	0.0365 (15)	0.0015 (15)	0.0064 (14)	0.0037 (13)
C7	0.0417 (18)	0.0343 (14)	0.0351 (15)	0.0016 (13)	0.0030 (13)	0.0008 (11)
C8	0.046 (2)	0.0450 (17)	0.0411 (16)	0.0004 (14)	0.0040 (14)	−0.0065 (13)
C9	0.0437 (19)	0.0457 (17)	0.0527 (18)	0.0012 (15)	−0.0007 (15)	−0.0013 (14)
C10	0.055 (2)	0.0404 (16)	0.0364 (16)	−0.0002 (15)	−0.0079 (15)	−0.0013 (13)
C11	0.063 (2)	0.0386 (16)	0.0371 (16)	0.0079 (16)	0.0003 (15)	−0.0010 (13)
C12	0.0444 (19)	0.0350 (14)	0.0353 (15)	0.0048 (13)	0.0047 (14)	0.0047 (12)

Geometric parameters (Å, º) top

S1—C1	1.786 (3)	C2—C3	1.370 (4)
S1—C7	1.766 (3)	C3—C4	1.373 (4)
O1—N1	1.216 (3)	C4—C5	1.369 (4)
O2—N1	1.218 (3)	C5—C6	1.374 (4)
O3—N2	1.218 (4)	C7—C8	1.399 (4)
O4—N2	1.212 (4)	C7—C12	1.405 (3)
O5—N3	1.222 (4)	C8—C9	1.376 (4)
O6—N3	1.224 (4)	C9—C10	1.387 (4)
O7—N4	1.220 (3)	C10—C11	1.363 (4)
O8—N4	1.223 (3)	C11—C12	1.386 (4)
N1—C2	1.477 (3)	C3—H3	0.9300
N2—C4	1.478 (4)	C5—H5	0.9300
N3—C10	1.466 (4)	C6—H6	0.9300
N4—C12	1.462 (4)	C8—H8	0.9300
C1—C2	1.387 (4)	C9—H9	0.9300
C1—C6	1.390 (4)	C11—H11	0.9300

C1—S1—C7	101.22 (13)	S1—C7—C8	122.26 (19)
O1—N1—O2	124.8 (3)	S1—C7—C12	121.5 (2)
O1—N1—C2	118.0 (2)	C8—C7—C12	116.3 (2)
O2—N1—C2	117.2 (2)	C7—C8—C9	122.2 (2)
O3—N2—O4	124.1 (3)	C8—C9—C10	119.0 (3)
O3—N2—C4	117.9 (3)	N3—C10—C9	119.0 (3)
O4—N2—C4	118.0 (3)	N3—C10—C11	119.6 (2)
O5—N3—O6	123.9 (3)	C9—C10—C11	121.4 (3)
O5—N3—C10	118.0 (3)	C10—C11—C12	118.9 (2)
O6—N3—C10	118.0 (3)	N4—C12—C7	121.3 (2)
O7—N4—O8	122.6 (3)	N4—C12—C11	116.5 (2)
O7—N4—C12	119.2 (2)	C7—C12—C11	122.2 (3)
O8—N4—C12	118.3 (2)	C2—C3—H3	121.00
S1—C1—C2	123.51 (19)	C4—C3—H3	121.00
S1—C1—C6	118.9 (2)	C4—C5—H5	121.00
C2—C1—C6	117.0 (2)	C6—C5—H5	121.00
N1—C2—C1	120.6 (2)	C1—C6—H6	119.00
N1—C2—C3	116.4 (2)	C5—C6—H6	119.00
C1—C2—C3	123.0 (2)	C7—C8—H8	119.00
C2—C3—C4	117.3 (2)	C9—C8—H8	119.00
N2—C4—C3	118.7 (3)	C8—C9—H9	121.00
N2—C4—C5	118.7 (3)	C10—C9—H9	120.00
C3—C4—C5	122.7 (3)	C10—C11—H11	121.00
C4—C5—C6	118.5 (3)	C12—C11—H11	121.00
C1—C6—C5	121.6 (2)

C7—S1—C1—C2	105.6 (2)	C6—C1—C2—C3	0.1 (4)
C7—S1—C1—C6	−83.5 (2)	S1—C1—C6—C5	−172.9 (2)
C1—S1—C7—C8	−6.2 (2)	C2—C1—C6—C5	−1.3 (4)
C1—S1—C7—C12	171.83 (19)	N1—C2—C3—C4	−179.0 (3)
O1—N1—C2—C1	−46.5 (4)	C1—C2—C3—C4	1.0 (4)
O1—N1—C2—C3	133.5 (3)	C2—C3—C4—N2	178.6 (3)
O2—N1—C2—C1	132.4 (3)	C2—C3—C4—C5	−1.0 (4)
O2—N1—C2—C3	−47.7 (4)	N2—C4—C5—C6	−179.7 (3)
O3—N2—C4—C3	3.8 (4)	C3—C4—C5—C6	−0.1 (5)
O3—N2—C4—C5	−176.6 (3)	C4—C5—C6—C1	1.3 (4)
O4—N2—C4—C3	−176.7 (3)	S1—C7—C8—C9	176.4 (2)
O4—N2—C4—C5	2.9 (4)	C12—C7—C8—C9	−1.7 (4)
O5—N3—C10—C9	1.8 (4)	S1—C7—C12—N4	2.1 (3)
O5—N3—C10—C11	−179.0 (3)	S1—C7—C12—C11	−175.55 (18)
O6—N3—C10—C9	−177.6 (3)	C8—C7—C12—N4	−179.7 (2)
O6—N3—C10—C11	1.7 (4)	C8—C7—C12—C11	2.6 (3)
O7—N4—C12—C7	175.5 (2)	C7—C8—C9—C10	−0.5 (4)
O7—N4—C12—C11	−6.8 (3)	C8—C9—C10—N3	−178.9 (3)
O8—N4—C12—C7	−5.0 (3)	C8—C9—C10—C11	1.9 (4)
O8—N4—C12—C11	172.8 (2)	N3—C10—C11—C12	179.7 (2)
S1—C1—C2—N1	−8.8 (4)	C9—C10—C11—C12	−1.0 (4)
S1—C1—C2—C3	171.3 (2)	C10—C11—C12—N4	−179.1 (2)
C6—C1—C2—N1	−179.9 (3)	C10—C11—C12—C7	−1.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O8ⁱ	0.93	2.54	3.080 (3)	117
C6—H6···O7ⁱⁱ	0.93	2.49	3.364 (3)	156
C11—H11···O2ⁱⁱⁱ	0.93	2.57	3.489 (3)	168

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₆N₄O₈S
M_r	366.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.9428 (12), 7.3693 (9), 19.743 (2)
β (°)	95.525 (8)
V (Å³)	1439.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.15 × 0.06 × 0.03

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.958, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	15342, 2949, 1651
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.110, 0.99
No. of reflections	2949
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O8ⁱ	0.93	2.54	3.080 (3)	117
C6—H6···O7ⁱⁱ	0.93	2.49	3.364 (3)	156
C11—H11···O2ⁱⁱⁱ	0.93	2.57	3.489 (3)	168

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x, −y+1/2, z−1/2.

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Volume 68| Part 11| November 2012| Page o3116

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