3,3'-Bis(4-nitro-phen-yl)-1,1'-(p-phenyl-ene)dithio-urea dimethyl sulfoxide disolvate.

The asymmetric unit of the title compound, C(22)H(16)N(6)O(6)S(2)·2C(2)H(6)OS, consists of one half-mol-ecule of the centrosymmetric thiourea derivative and one molecule of dimethyl sulfoxide (DMSO). The carbonyl group forms an intra-molecular hydrogen bond with the NH group, creating a six-membered (C-N-C-N-H⋯O) ring. Two other N-H⋯O hydro-gen bonds link one mol-ecule of the thio-urea to two mol-ecules 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

C22H16N6O6S2·2C2n class="CellLine">H6OS

M = 680.78

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.199

S = 0.96

2684 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.43 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H16N6O6S2·2C2H6OS	F000 = 708
Mr = 680.78	Dx = 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 = 3.3–25.3º
c = 20.449 (2) Å	µ = 0.37 mm−1
β = 106.353 (2)º	T = 298 (2) K
V = 1535.5 (4) Å3	Needle-shaped, yellow
Z = 2	0.33 × 0.17 × 0.11 mm

Bruker SMART CCD area-detector diffractometer	2684 independent reflections
Radiation source: fine-focus sealed tube	1547 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.097
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −11→13
Tmin = 0.888, Tmax = 0.961	k = −7→7
7318 measured reflections	l = −24→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069	H-atom parameters constrained
wR(F2) = 0.199	w = 1/[σ2(Fo2) + (0.1071P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
2684 reflections	Δρmax = 0.44 e Å−3
199 parameters	Δρmin = −0.43 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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