3,3′-Bis(4-nitro­phen­yl)-1,1′-(p-phenyl­ene)dithio­urea dimethyl sulfoxide disolvate

Dong, W.-K.; Yan, H.-B.; Chai, L.-Q.; Lv, Z.-W.; Zhao, C.-Y.

doi:10.1107/S160053680801430X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1097

doi:10.1107/S160053680801430X

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3,3′-Bis(4-nitrophenyl)-1,1′-(p-phenylene)dithiourea dimethyl sulfoxide disolvate

Wen-Kui Dong,^a ^* Hai-Bo Yan,^a Lan-Qin Chai,^a Zhong-Wu Lv ^a and Chun-Yu Zhao ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 5 April 2008; accepted 13 May 2008; online 17 May 2008)

The asymmetric unit of the title compound, C₂₂H₁₆N₆O₆S₂·2C₂H₆OS, consists of one half-molecule of the centrosymmetric thiourea derivative and one molecule of dimethyl sulfoxide (DMSO). The carbonyl group forms an intramolecular hydrogen bond with the NH group, creating a six-membered (C—N—C—N—H⋯O) ring. Two other N—H⋯O hydrogen bonds link one molecule of the thiourea to two molecules of DMSO.

Related literature

For related literature, see: Burrows et al. (1997 ); Dong et al. (2006 , 2007 ); Foss et al. (2004 ); Valdés-Martínez et al. (2000 , 2004 ); Zhang et al. (2006 ); Huang et al. (2006 ).

Experimental

Crystal data

C₂₂H₁₆N₆O₆S₂·2C₂H₆OS
M_r = 680.78
Monoclinic, P 2₁ /c
a = 11.6949 (18) Å
b = 6.6916 (11) Å
c = 20.449 (2) Å
β = 106.353 (2)°
V = 1535.5 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 298 (2) K
0.33 × 0.17 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.888, T_max = 0.961
7318 measured reflections
2684 independent reflections
1547 reflections with I > 2σ(I)
R_int = 0.097

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.199
S = 0.96
2684 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	2.09	2.942 (5)	169
N2—H2⋯O1	0.86	1.84	2.579 (5)	143

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801430X/fl2195sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801430X/fl2195Isup2.hkl

checkCIF report

Comment top

Thiourea and its derivatives are of interest to us because of their varied biological activity as well as their ability to form strong H bonds as both donors and acceptors (Valdés-Martínez, et al., 2000; Jesus, et al., 2004, Burrows et al., 1997), and their tendency to coordinate with metal ions (Huang, et al., 2006; Foss, et al., 2004). In recent years, thioureas have been recognized as important neutral receptors because of their anion recognition properties (Zhang, et al., 2006) and for their ability to easily form intramolecular hydrogen bonds such as between the benzoyl (CO) and the N—H group of acylthioureas (Dong et al., 2006). In continuation of our previous studies on the synthesis and structural characterization of N-benzoyl-N'-(3-pyridyl)thiourea (II) (Dong, et al., 2006) and N,N'-(1,6-hexamethylene)-bis(benzoylthiourea) (Dong, et al., 2007), a novel bisbenzoylthiourea which crystallized as a dimethyl sulfoxide disolvate (I) has now been synthesized and structurally characterized.

The crystal structure of (I) is built up by one N, N'-(p-phenyl)-bis(p-nitro)benzoylthiourea molecule and two dimethyl sulfoxide solvent molecules. The carbonyl group of the thiourea forms an intramolecular hydrogen bond with the N—H group to form a six-membered (C/N/C/N/H/O) ring. The C=O bond length at 1.225 (5)Å is longer than the average C=O bond length (1.200 Å). This is most likely due to the intramolecular hydrogen bonding which is similar to the situation found in the structure of (II) (Dong, et al., 2006).

There are also N—H···O hydrogen bonds between N1 of the thiourea and the O atoms of the DMSO S=O groups which, together with other intermolecular C—H···O and C—H···S interactions, stabilize the three-dimensional structure of (I).

Related literature top

For related literature, see: Burrows et al. (1997); Dong et al. (2006, 2007); Foss et al. (2004); Valdés-Martínez et al. (2000, 2004); Zhang et al. (2006); Huang et al. (2006).

Experimental top

(p-Nitro)benzoyl chloride (1.86 g, 10 mmol) was reacted with ammonium thiocyanate (1.14 g, 15 mmol) in CH₂Cl₂ (25 ml) solution under solid-liquid phase transfer catalysis, using polyethylene glycol-400 (0.18 g) as the catalyst, to give the corresponding (p-nitro)benzoyl isothiocyanate under stirring at the room temperature. This was followed by slow addition of 15 ml CH₂Cl₂ solution dissolved p-phenylenediamine (1.60 g, 0.01 mmol). The corresponding yellow compound precipitated immediately. The product was filtered, washed with water and CH₂Cl₂, dried, and recrystallized from THF to give the titled thiourea. Yield, 72.6%. m. p. 243 - 244 °C. Anal. Calc. for C₂₂H₁₆N₆O₆S₂ (%): C, 50.38; H, 3.07; N, 16.02. Found: C, 50.27; H, 3.15; N, 15.99. Selected IR data (cm^-1, KBr pellet): 3341, 3191 (ν NH), 1675 (ν C=O), 1152 (ν C=S). ¹H NMR (400 MHz, DMSO-d6, δ, p.p.m.): 8.05 (d, J = 17.2 Hz, 4H, ArH), 8.19 (d, J = 8.2 Hz, 4H, ArH), 8.34 (dd, J = 17.2, 7.2 Hz, 4H, ArH), 11.98 (s, 2H, NH), 12.42 (s, 2H, NH).

A DMSO solution of the thiourea was placed in a hexane atmosphere, after about one week, along with diffusion of hexane into the DMSO solution, yellow needle-shaped single crystals suitable for X-ray crystallographic analysis were obtained.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecule structure of (I) with the atom numbering. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.

3,3'-Bis(4-nitrophenyl)-1,1'-(p-phenylene)dithiourea dimethyl sulfoxide disolvate top

Crystal data top

C₂₂H₁₆N₆O₆S₂·2C₂H₆OS	F(000) = 708
M_r = 680.78	D_x = 1.472 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.6949 (18) Å	Cell parameters from 1517 reflections
b = 6.6916 (11) Å	θ = 3.3–25.3°
c = 20.449 (2) Å	µ = 0.37 mm⁻¹
β = 106.353 (2)°	T = 298 K
V = 1535.5 (4) Å³	Needle-shaped, yellow
Z = 2	0.33 × 0.17 × 0.11 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2684 independent reflections
Radiation source: fine-focus sealed tube	1547 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.097
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→13
T_min = 0.888, T_max = 0.961	k = −7→7
7318 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.199	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.1071P)²] where P = (F_o² + 2F_c²)/3
2684 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₂H₁₆N₆O₆S₂·2C₂H₆OS	V = 1535.5 (4) Å³
M_r = 680.78	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6949 (18) Å	µ = 0.37 mm⁻¹
b = 6.6916 (11) Å	T = 298 K
c = 20.449 (2) Å	0.33 × 0.17 × 0.11 mm
β = 106.353 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2684 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1547 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.961	R_int = 0.097
7318 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.199	H-atom parameters constrained
S = 0.97	Δρ_max = 0.44 e Å⁻³
2684 reflections	Δρ_min = −0.43 e Å⁻³
199 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
N1	0.7828 (3)	0.3522 (5)	0.51603 (16)	0.0505 (8)
H1	0.7673	0.2724	0.5454	0.061*
N2	0.8719 (3)	0.6436 (5)	0.49516 (16)	0.0507 (9)
H2	0.8343	0.6109	0.4541	0.061*
N3	0.4791 (3)	−0.4240 (5)	0.36972 (18)	0.0565 (9)
O1	0.7411 (3)	0.4141 (5)	0.40259 (14)	0.0614 (8)
O2	0.4552 (3)	−0.4678 (5)	0.31005 (16)	0.0733 (10)
O3	0.4566 (3)	−0.5286 (5)	0.41241 (17)	0.0776 (10)
O4	0.7382 (3)	0.1230 (6)	0.62917 (14)	0.0782 (10)
S1	0.91836 (14)	0.5258 (2)	0.62543 (6)	0.0858 (6)
S2	0.82807 (12)	0.0691 (2)	0.69426 (6)	0.0711 (5)
C1	0.8572 (4)	0.5173 (6)	0.5429 (2)	0.0502 (10)
C2	0.9391 (3)	0.8218 (6)	0.5010 (2)	0.0454 (10)
C3	0.9492 (4)	0.9013 (7)	0.4410 (2)	0.0557 (11)
H3	0.9141	0.8344	0.4004	0.067*
C4	1.0090 (4)	1.0755 (7)	0.4389 (2)	0.0562 (11)
H4	1.0150	1.1251	0.3975	0.067*
C5	0.7326 (3)	0.3047 (6)	0.44901 (19)	0.0455 (10)
C6	0.6642 (3)	0.1137 (6)	0.43250 (18)	0.0443 (9)
C7	0.6443 (4)	−0.0164 (6)	0.4804 (2)	0.0501 (10)
H7	0.6723	0.0141	0.5265	0.060*
C8	0.5824 (4)	−0.1933 (7)	0.4596 (2)	0.0548 (11)
H8	0.5674	−0.2810	0.4915	0.066*
C9	0.5441 (3)	−0.2359 (6)	0.39199 (19)	0.0461 (10)
C10	0.5631 (4)	−0.1108 (7)	0.3439 (2)	0.0600 (12)
H10	0.5363	−0.1438	0.2979	0.072*
C11	0.6225 (4)	0.0652 (7)	0.3643 (2)	0.0592 (12)
H11	0.6349	0.1531	0.3318	0.071*
C12	0.8181 (5)	0.2507 (9)	0.7540 (2)	0.0870 (17)
H12A	0.8448	0.3769	0.7414	0.131*
H12B	0.8671	0.2124	0.7983	0.131*
H12C	0.7368	0.2624	0.7550	0.131*
C13	0.7650 (6)	−0.1309 (11)	0.7298 (3)	0.120 (2)
H13A	0.6928	−0.0866	0.7388	0.180*
H13B	0.8206	−0.1736	0.7716	0.180*
H13C	0.7477	−0.2405	0.6983	0.180*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.050 (2)	0.046 (2)	0.0538 (19)	−0.0108 (17)	0.0109 (15)	0.0002 (17)
N2	0.0460 (19)	0.047 (2)	0.0551 (19)	−0.0107 (16)	0.0077 (15)	−0.0008 (17)
N3	0.064 (2)	0.048 (2)	0.055 (2)	−0.0041 (18)	0.0123 (18)	0.0011 (18)
O1	0.0683 (19)	0.057 (2)	0.0569 (17)	−0.0188 (15)	0.0140 (14)	0.0064 (15)
O2	0.094 (2)	0.065 (2)	0.0564 (19)	−0.0207 (18)	0.0137 (17)	−0.0127 (16)
O3	0.100 (3)	0.064 (2)	0.064 (2)	−0.0294 (19)	0.0153 (18)	0.0067 (17)
O4	0.090 (2)	0.090 (3)	0.0495 (18)	−0.021 (2)	0.0117 (16)	0.0026 (17)
S1	0.1133 (12)	0.0803 (10)	0.0544 (8)	−0.0440 (9)	0.0080 (7)	−0.0012 (6)
S2	0.0732 (9)	0.0804 (10)	0.0590 (7)	0.0026 (7)	0.0174 (6)	−0.0010 (6)
C1	0.043 (2)	0.048 (3)	0.059 (3)	−0.0024 (19)	0.0118 (19)	−0.002 (2)
C2	0.035 (2)	0.040 (2)	0.060 (2)	−0.0015 (17)	0.0101 (17)	0.0030 (19)
C3	0.059 (3)	0.049 (3)	0.054 (2)	−0.009 (2)	0.0082 (19)	−0.007 (2)
C4	0.064 (3)	0.055 (3)	0.050 (2)	−0.011 (2)	0.016 (2)	−0.002 (2)
C5	0.035 (2)	0.048 (3)	0.050 (2)	−0.0030 (18)	0.0056 (17)	0.001 (2)
C6	0.040 (2)	0.047 (2)	0.046 (2)	−0.0016 (18)	0.0121 (17)	0.0012 (18)
C7	0.051 (2)	0.053 (3)	0.042 (2)	−0.006 (2)	0.0060 (18)	−0.0026 (19)
C8	0.062 (3)	0.052 (3)	0.053 (2)	−0.008 (2)	0.021 (2)	0.004 (2)
C9	0.046 (2)	0.042 (2)	0.047 (2)	−0.0039 (18)	0.0067 (17)	0.0017 (19)
C10	0.073 (3)	0.061 (3)	0.042 (2)	−0.018 (2)	0.011 (2)	−0.001 (2)
C11	0.073 (3)	0.060 (3)	0.046 (2)	−0.023 (2)	0.017 (2)	0.008 (2)
C12	0.101 (4)	0.097 (4)	0.059 (3)	0.013 (3)	0.016 (3)	−0.001 (3)
C13	0.158 (6)	0.091 (5)	0.100 (4)	−0.022 (5)	0.020 (4)	0.024 (4)

Geometric parameters (Å, º) top

N1—C5	1.368 (4)	C4—H4	0.9300
N1—C1	1.418 (5)	C5—C6	1.495 (6)
N1—H1	0.8600	C6—C7	1.379 (6)
N2—C1	1.338 (5)	C6—C11	1.380 (5)
N2—C2	1.414 (5)	C7—C8	1.390 (6)
N2—H2	0.8600	C7—H7	0.9300
N3—O3	1.204 (4)	C8—C9	1.358 (5)
N3—O2	1.209 (4)	C8—H8	0.9300
N3—C9	1.475 (5)	C9—C10	1.356 (6)
O1—C5	1.225 (5)	C10—C11	1.371 (6)
O4—S2	1.490 (3)	C10—H10	0.9300
S1—C1	1.638 (4)	C11—H11	0.9300
S2—C12	1.750 (5)	C12—H12A	0.9600
S2—C13	1.779 (6)	C12—H12B	0.9600
C2—C3	1.372 (5)	C12—H12C	0.9600
C2—C4ⁱ	1.389 (5)	C13—H13A	0.9600
C3—C4	1.367 (6)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C2ⁱ	1.389 (5)

C5—N1—C1	127.8 (3)	C11—C6—C5	116.4 (3)
C5—N1—H1	116.1	C6—C7—C8	119.9 (4)
C1—N1—H1	116.1	C6—C7—H7	120.1
C1—N2—C2	130.8 (3)	C8—C7—H7	120.1
C1—N2—H2	114.6	C9—C8—C7	119.0 (4)
C2—N2—H2	114.6	C9—C8—H8	120.5
O3—N3—O2	123.7 (4)	C7—C8—H8	120.5
O3—N3—C9	118.1 (3)	C10—C9—C8	122.3 (4)
O2—N3—C9	118.1 (4)	C10—C9—N3	118.6 (3)
O4—S2—C12	106.6 (2)	C8—C9—N3	119.2 (4)
O4—S2—C13	106.1 (2)	C9—C10—C11	118.8 (4)
C12—S2—C13	96.9 (3)	C9—C10—H10	120.6
N2—C1—N1	113.6 (3)	C11—C10—H10	120.6
N2—C1—S1	128.4 (3)	C10—C11—C6	121.0 (4)
N1—C1—S1	117.9 (3)	C10—C11—H11	119.5
C3—C2—C4ⁱ	118.2 (4)	C6—C11—H11	119.5
C3—C2—N2	115.9 (4)	S2—C12—H12A	109.5
C4ⁱ—C2—N2	125.8 (4)	S2—C12—H12B	109.5
C4—C3—C2	122.1 (4)	H12A—C12—H12B	109.5
C4—C3—H3	118.9	S2—C12—H12C	109.5
C2—C3—H3	118.9	H12A—C12—H12C	109.5
C3—C4—C2ⁱ	119.6 (4)	H12B—C12—H12C	109.5
C3—C4—H4	120.2	S2—C13—H13A	109.5
C2ⁱ—C4—H4	120.2	S2—C13—H13B	109.5
O1—C5—N1	122.2 (4)	H13A—C13—H13B	109.5
O1—C5—C6	119.4 (3)	S2—C13—H13C	109.5
N1—C5—C6	118.4 (4)	H13A—C13—H13C	109.5
C7—C6—C11	119.1 (4)	H13B—C13—H13C	109.5
C7—C6—C5	124.5 (3)

C2—N2—C1—N1	−179.4 (4)	C11—C6—C7—C8	−0.3 (6)
C2—N2—C1—S1	−2.6 (7)	C5—C6—C7—C8	−178.1 (4)
C5—N1—C1—N2	4.2 (6)	C6—C7—C8—C9	1.0 (6)
C5—N1—C1—S1	−173.0 (3)	C7—C8—C9—C10	−0.7 (7)
C1—N2—C2—C3	170.9 (4)	C7—C8—C9—N3	179.6 (4)
C1—N2—C2—C4ⁱ	−11.5 (7)	O3—N3—C9—C10	−175.8 (4)
C4ⁱ—C2—C3—C4	0.6 (7)	O2—N3—C9—C10	6.8 (6)
N2—C2—C3—C4	178.4 (4)	O3—N3—C9—C8	4.0 (6)
C2—C3—C4—C2ⁱ	−0.6 (7)	O2—N3—C9—C8	−173.4 (4)
C1—N1—C5—O1	−5.3 (6)	C8—C9—C10—C11	−0.3 (7)
C1—N1—C5—C6	175.5 (4)	N3—C9—C10—C11	179.4 (4)
O1—C5—C6—C7	−177.0 (4)	C9—C10—C11—C6	1.1 (7)
N1—C5—C6—C7	2.3 (6)	C7—C6—C11—C10	−0.7 (7)
O1—C5—C6—C11	5.2 (6)	C5—C6—C11—C10	177.2 (4)
N1—C5—C6—C11	−175.6 (4)

Symmetry code: (i) −x+2, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	2.09	2.942 (5)	169
N2—H2···O1	0.86	1.84	2.579 (5)	143

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆N₆O₆S₂·2C₂H₆OS
M_r	680.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.6949 (18), 6.6916 (11), 20.449 (2)
β (°)	106.353 (2)
V (Å³)	1535.5 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.33 × 0.17 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.888, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	7318, 2684, 1547
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.199, 0.97
No. of reflections	2684
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.43

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.860	2.092	2.942 (5)	169.39
N2—H2···O1	0.860	1.839	2.579 (5)	143.06

Acknowledgements

We gratefully acknowledge support of this work by the Foundation of the Education Department of Gansu Province (No. 0604–01) and the `Qing Lan' Talent Engineering Funds of Lanzhou Jiaotong University (No. QL-03–01 A).

References

Burrows, A. D., Menzer, S. & Michael, D. (1997). J. Chem. Soc. Dalton Trans. pp. 4237–4240. CSD CrossRef Web of Science Google Scholar
Dong, W.-K., Yang, X.-Q. & Feng, J.-H. (2006). Acta Cryst. E62, o3459–o3460. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dong, W.-K., Yang, X.-Q., Xu, L., Wang, L., Liu, G. L. & Feng, J.-H. (2007). Z. Kristallogr. New Cryst. Struct. 222, 279–280. CAS Google Scholar
Foss, O., Husebye, S. & Törnroos, K. (2004). Polyhedron, 23, 3021–3032. Web of Science CSD CrossRef CAS Google Scholar
Huang, J., Song, J.-R. & Ren, Y.-H. (2006). Chin. J. Struct. Chem. 25, 168–172. CAS 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
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Valdés-Martínez, J., Hernández-Ortega, S., Ackerman, L. J., Li, D. T., Swearingen, J. K. & West, D. X. (2000). J. Mol. Struct. 524, 51–59. Google Scholar
Valdés-Martínez, J., Hernández-Ortega, S., Rubio, M., Li, D. T., Swearingen, J. K., Kaminsky, W., Kelman D. R. & West, D. X. (2004). J. Chem. Crystallogr. 34, 533–540. Google Scholar
Zhang, Y.-M., Xu, W.-X. & Zhou, Y.-Q. (2006). Acta Chim. Sinica, 64, 79–84. CAS Google Scholar

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Volume 64| Part 6| June 2008| Page o1097

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,3′-Bis(4-nitro­phen­yl)-1,1′-(p-phenyl­ene)di­thio­urea di­methyl sulfoxide disolvate

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organic compounds

3,3′-Bis(4-nitrophenyl)-1,1′-(p-phenylene)dithiourea dimethyl sulfoxide disolvate