1,2-Bis(N'-benzoyl-thio-ureido)benzene.

The title compound, C(22)H(18)N(4)O(2)S(2), was characterized by (1)H and (13)C NMR, solid-state IR spectroscopy and X-ray crystallographic techniques. The crystal structure determination reveals that the twisting modes of the two side arms are different [C-N-C-O and C-N-C-N torsion angles = -1.2 (3) and 1.1 (3)°, respectively, in one arm and 24.1 (3) and -5.1 (3)°, respectively, in the other]. The crystal structure involves N-H⋯O and N-H⋯S hydrogen bonds.

Related literature

For related structures: see Arslan et al. (2004 ▶); Avşar et al. (2003 ▶).

Experimental

Crystal data

C22H18N4O2S2

M = 434.52

Triclinic,

a = 7.179 (1) Å

b = 12.064 (2) Å

c = 12.476 (2) Å

α = 77.88 (5)°

β = 86.96 (5)°

γ = 77.91 (5)°

V = 1032.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 173 (2) K

0.10 × 0.10 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

12922 measured reflections

4671 independent reflections

3234 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.118

S = 1.04

4671 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Nonius, 1998 ▶); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008374/ww2115sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008374/ww2115Isup2.hkl

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

C22H18N4O2S2	Z = 2
Mr = 434.52	F000 = 452
Triclinic, P1	Dx = 1.397 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71069 Å
a = 7.179 (1) Å	Cell parameters from 6418 reflections
b = 12.064 (2) Å	θ = 1.0–27.5º
c = 12.476 (2) Å	µ = 0.29 mm−1
α = 77.88 (5)º	T = 173 (2) K
β = 86.96 (5)º	Prism, colorless
γ = 77.91 (5)º	0.10 × 0.10 × 0.10 mm
V = 1032.9 (3) Å3

Nonius KappaCCD diffractometer	3234 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
Monochromator: graphite	θmax = 27.4º
T = 173(2) K	θmin = 3.1º
ω scans	h = −9→8
Absorption correction: none	k = −15→15
12922 measured reflections	l = −16→14
4671 independent reflections

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.048P)2 + 0.1332P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
4671 reflections	Δρmax = 0.17 e Å−3
271 parameters	Δρmin = −0.24 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
S1	0.51586 (8)	0.37259 (4)	0.93513 (5)	0.0727 (2)
S2	0.83170 (8)	0.17089 (4)	0.50551 (4)	0.06579 (18)
O6	0.69327 (18)	0.01181 (10)	0.86202 (10)	0.0574 (3)
O7	0.5045 (2)	−0.09194 (11)	0.70005 (13)	0.0680 (4)
N1	0.5437 (2)	0.23196 (11)	0.78892 (12)	0.0473 (3)
HN1	0.5932	0.1610	0.7809	0.057*
N2	0.5204 (2)	0.12967 (12)	0.61750 (12)	0.0529 (4)
HN2	0.4517	0.0797	0.6504	0.064*
N3	0.6479 (2)	0.15035 (12)	0.96355 (12)	0.0515 (4)
HN3	0.6623	0.1608	1.0301	0.062*
N4	0.7603 (2)	−0.02950 (12)	0.61097 (12)	0.0536 (4)
HN4	0.8699	−0.0573	0.5818	0.064*
C1	0.5672 (2)	0.25055 (15)	0.88870 (15)	0.0487 (4)
C2	0.4547 (2)	0.30447 (14)	0.69408 (14)	0.0464 (4)
C3	0.3759 (3)	0.42184 (16)	0.68239 (17)	0.0617 (5)
H3	0.3854	0.4605	0.7402	0.074*
C4	0.2842 (3)	0.48218 (17)	0.5872 (2)	0.0740 (6)
H4	0.2306	0.5623	0.5801	0.089*
C5	0.2688 (3)	0.4288 (2)	0.5025 (2)	0.0798 (7)
H5	0.2044	0.4713	0.4374	0.096*
C6	0.3477 (3)	0.31235 (19)	0.51256 (18)	0.0724 (6)
H6	0.3376	0.2747	0.4541	0.087*
C7	0.4408 (3)	0.25085 (15)	0.60686 (15)	0.0516 (4)
C8	0.6935 (3)	0.08886 (14)	0.58002 (13)	0.0499 (4)
C9	0.7082 (2)	0.03836 (14)	0.95003 (14)	0.0432 (4)
C10	0.7920 (2)	−0.04822 (14)	1.04687 (14)	0.0439 (4)
C11	0.8139 (3)	−0.02222 (17)	1.14823 (16)	0.0581 (5)
H11	0.7708	0.0548	1.1588	0.070*
C12	0.8976 (3)	−0.1075 (2)	1.23359 (17)	0.0704 (6)
H12	0.9132	−0.0886	1.3023	0.084*
C13	0.9583 (3)	−0.2187 (2)	1.22008 (19)	0.0710 (6)
H13	1.0160	−0.2770	1.2792	0.085*
C14	0.9358 (3)	−0.24622 (18)	1.1207 (2)	0.0716 (6)
H14	0.9773	−0.3237	1.1113	0.086*
C15	0.8529 (3)	−0.16125 (16)	1.03435 (16)	0.0577 (5)
H15	0.8377	−0.1808	0.9659	0.069*
C16	0.6757 (3)	−0.10936 (15)	0.68221 (15)	0.0526 (4)
C17	0.8076 (3)	−0.21596 (14)	0.73653 (14)	0.0489 (4)
C18	0.9977 (3)	−0.21949 (15)	0.75364 (15)	0.0553 (5)
H18	1.0507	−0.1534	0.7249	0.066*
C19	1.1108 (3)	−0.31812 (19)	0.81204 (17)	0.0675 (5)
H19	1.2411	−0.3196	0.8238	0.081*
C20	1.0355 (4)	−0.41383 (19)	0.85309 (19)	0.0795 (7)
H20	1.1136	−0.4819	0.8931	0.095*
C21	0.8486 (4)	−0.41166 (18)	0.8367 (2)	0.0851 (7)
H21	0.7973	−0.4784	0.8656	0.102*
C22	0.7330 (3)	−0.31380 (17)	0.77883 (18)	0.0671 (5)
H22	0.6028	−0.3132	0.7679	0.080*

	U11	U22	U33	U12	U13	U23
S1	0.0863 (4)	0.0478 (3)	0.0852 (4)	0.0036 (3)	−0.0164 (3)	−0.0301 (3)
S2	0.0795 (4)	0.0420 (3)	0.0619 (3)	0.0045 (2)	0.0121 (3)	0.0005 (2)
O6	0.0759 (9)	0.0422 (7)	0.0499 (7)	0.0008 (6)	−0.0060 (6)	−0.0115 (6)
O7	0.0617 (9)	0.0473 (8)	0.0933 (11)	−0.0070 (7)	−0.0039 (7)	−0.0139 (7)
N1	0.0511 (8)	0.0349 (7)	0.0515 (9)	0.0007 (6)	0.0017 (6)	−0.0090 (6)
N2	0.0600 (9)	0.0381 (8)	0.0557 (9)	−0.0012 (7)	−0.0002 (7)	−0.0074 (7)
N3	0.0593 (9)	0.0430 (8)	0.0502 (9)	0.0006 (7)	−0.0080 (7)	−0.0139 (7)
N4	0.0681 (10)	0.0359 (8)	0.0503 (9)	0.0028 (7)	0.0040 (7)	−0.0085 (7)
C1	0.0435 (9)	0.0428 (10)	0.0598 (11)	−0.0055 (7)	0.0006 (8)	−0.0136 (8)
C2	0.0430 (9)	0.0369 (9)	0.0525 (10)	−0.0003 (7)	0.0050 (8)	−0.0031 (8)
C3	0.0693 (13)	0.0397 (10)	0.0671 (13)	0.0032 (9)	0.0049 (10)	−0.0062 (9)
C4	0.0797 (15)	0.0424 (11)	0.0831 (16)	0.0110 (10)	0.0013 (12)	0.0008 (11)
C5	0.0891 (16)	0.0591 (13)	0.0713 (15)	0.0162 (12)	−0.0161 (12)	0.0041 (11)
C6	0.0861 (15)	0.0581 (13)	0.0622 (13)	0.0073 (11)	−0.0157 (11)	−0.0064 (10)
C7	0.0535 (10)	0.0379 (9)	0.0553 (11)	0.0037 (8)	0.0004 (8)	−0.0049 (8)
C8	0.0668 (12)	0.0384 (9)	0.0400 (9)	0.0022 (8)	−0.0079 (8)	−0.0088 (7)
C9	0.0383 (9)	0.0412 (9)	0.0501 (10)	−0.0093 (7)	0.0036 (7)	−0.0091 (8)
C10	0.0332 (8)	0.0460 (10)	0.0506 (10)	−0.0102 (7)	0.0046 (7)	−0.0043 (8)
C11	0.0636 (12)	0.0558 (12)	0.0549 (11)	−0.0167 (10)	−0.0032 (9)	−0.0061 (9)
C12	0.0716 (14)	0.0806 (16)	0.0575 (12)	−0.0253 (12)	−0.0119 (10)	0.0019 (11)
C13	0.0523 (12)	0.0764 (16)	0.0692 (15)	−0.0135 (11)	−0.0067 (10)	0.0209 (12)
C14	0.0662 (13)	0.0516 (12)	0.0828 (16)	0.0014 (10)	0.0049 (11)	0.0031 (11)
C15	0.0589 (12)	0.0489 (11)	0.0595 (12)	−0.0048 (9)	0.0052 (9)	−0.0053 (9)
C16	0.0672 (13)	0.0398 (10)	0.0523 (11)	−0.0073 (9)	−0.0018 (9)	−0.0159 (8)
C17	0.0652 (12)	0.0359 (9)	0.0435 (9)	−0.0045 (8)	0.0058 (8)	−0.0108 (7)
C18	0.0713 (13)	0.0439 (10)	0.0480 (10)	−0.0079 (9)	0.0011 (9)	−0.0078 (8)
C19	0.0661 (13)	0.0658 (13)	0.0600 (12)	0.0041 (11)	0.0022 (10)	−0.0071 (10)
C20	0.0836 (17)	0.0568 (13)	0.0730 (15)	0.0153 (12)	0.0142 (12)	0.0095 (11)
C21	0.0904 (18)	0.0458 (12)	0.1012 (18)	−0.0055 (12)	0.0261 (14)	0.0099 (12)
C22	0.0682 (13)	0.0479 (11)	0.0770 (14)	−0.0055 (10)	0.0124 (11)	−0.0044 (10)

S1—C1	1.6574 (18)	C6—H6	0.9500
S2—C8	1.660 (2)	C9—C10	1.482 (2)
O6—C9	1.222 (2)	C10—C15	1.381 (3)
O7—C16	1.219 (2)	C10—C11	1.390 (3)
N1—C1	1.335 (2)	C11—C12	1.379 (3)
N1—C2	1.409 (2)	C11—H11	0.9500
N1—HN1	0.8800	C12—C13	1.364 (3)
N2—C8	1.336 (2)	C12—H12	0.9500
N2—C7	1.435 (2)	C13—C14	1.375 (3)
N2—HN2	0.8800	C13—H13	0.9500
N3—C9	1.373 (2)	C14—C15	1.384 (3)
N3—C1	1.400 (2)	C14—H14	0.9500
N3—HN3	0.8800	C15—H15	0.9500
N4—C16	1.384 (2)	C16—C17	1.484 (3)
N4—C8	1.385 (2)	C17—C18	1.383 (3)
N4—HN4	0.8800	C17—C22	1.390 (3)
C2—C3	1.390 (3)	C18—C19	1.379 (3)
C2—C7	1.395 (3)	C18—H18	0.9500
C3—C4	1.376 (3)	C19—C20	1.368 (3)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.368 (3)	C20—C21	1.361 (3)
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.382 (3)	C21—C22	1.378 (3)
C5—H5	0.9500	C21—H21	0.9500
C6—C7	1.375 (3)	C22—H22	0.9500
C1—N1—C2	132.18 (15)	C15—C10—C11	118.55 (18)
C1—N1—HN1	113.9	C15—C10—C9	117.42 (16)
C2—N1—HN1	113.9	C11—C10—C9	124.03 (16)
C8—N2—C7	123.32 (15)	C12—C11—C10	120.43 (19)
C8—N2—HN2	118.3	C12—C11—H11	119.8
C7—N2—HN2	118.3	C10—C11—H11	119.8
C9—N3—C1	130.47 (15)	C13—C12—C11	120.5 (2)
C9—N3—HN3	114.8	C13—C12—H12	119.7
C1—N3—HN3	114.8	C11—C12—H12	119.7
C16—N4—C8	127.91 (16)	C12—C13—C14	119.8 (2)
C16—N4—HN4	116.0	C12—C13—H13	120.1
C8—N4—HN4	116.0	C14—C13—H13	120.1
N1—C1—N3	113.59 (14)	C13—C14—C15	120.1 (2)
N1—C1—S1	129.80 (15)	C13—C14—H14	119.9
N3—C1—S1	116.61 (13)	C15—C14—H14	119.9
C3—C2—C7	118.45 (17)	C10—C15—C14	120.55 (19)
C3—C2—N1	125.64 (17)	C10—C15—H15	119.7
C7—C2—N1	115.87 (15)	C14—C15—H15	119.7
C4—C3—C2	120.1 (2)	O7—C16—N4	121.91 (18)
C4—C3—H3	119.9	O7—C16—C17	122.55 (18)
C2—C3—H3	119.9	N4—C16—C17	115.53 (17)
C5—C4—C3	121.14 (19)	C18—C17—C22	118.80 (18)
C5—C4—H4	119.4	C18—C17—C16	122.79 (16)
C3—C4—H4	119.4	C22—C17—C16	118.25 (17)
C4—C5—C6	119.4 (2)	C19—C18—C17	120.57 (18)
C4—C5—H5	120.3	C19—C18—H18	119.7
C6—C5—H5	120.3	C17—C18—H18	119.7
C7—C6—C5	120.3 (2)	C20—C19—C18	120.0 (2)
C7—C6—H6	119.9	C20—C19—H19	120.0
C5—C6—H6	119.9	C18—C19—H19	120.0
C6—C7—C2	120.62 (17)	C21—C20—C19	120.1 (2)
C6—C7—N2	120.04 (18)	C21—C20—H20	120.0
C2—C7—N2	119.32 (16)	C19—C20—H20	120.0
N2—C8—N4	116.00 (17)	C20—C21—C22	120.8 (2)
N2—C8—S2	124.29 (13)	C20—C21—H21	119.6
N4—C8—S2	119.66 (14)	C22—C21—H21	119.6
O6—C9—N3	121.30 (16)	C21—C22—C17	119.7 (2)
O6—C9—C10	121.83 (15)	C21—C22—H22	120.1
N3—C9—C10	116.87 (15)	C17—C22—H22	120.1
C2—N1—C1—N3	173.63 (15)	N3—C9—C10—C15	179.91 (15)
C2—N1—C1—S1	−6.5 (3)	O6—C9—C10—C11	179.29 (16)
C9—N3—C1—N1	1.1 (3)	N3—C9—C10—C11	−0.6 (2)
C9—N3—C1—S1	−178.77 (14)	C15—C10—C11—C12	1.1 (3)
C1—N1—C2—C3	4.2 (3)	C9—C10—C11—C12	−178.39 (16)
C1—N1—C2—C7	−173.60 (17)	C10—C11—C12—C13	−0.7 (3)
C7—C2—C3—C4	1.0 (3)	C11—C12—C13—C14	0.0 (3)
N1—C2—C3—C4	−176.74 (18)	C12—C13—C14—C15	0.4 (3)
C2—C3—C4—C5	−0.1 (3)	C11—C10—C15—C14	−0.7 (3)
C3—C4—C5—C6	−0.4 (4)	C9—C10—C15—C14	178.77 (16)
C4—C5—C6—C7	0.0 (4)	C13—C14—C15—C10	0.0 (3)
C5—C6—C7—C2	0.9 (3)	C8—N4—C16—O7	24.1 (3)
C5—C6—C7—N2	179.2 (2)	C8—N4—C16—C17	−154.85 (16)
C3—C2—C7—C6	−1.4 (3)	O7—C16—C17—C18	−153.22 (18)
N1—C2—C7—C6	176.58 (18)	N4—C16—C17—C18	25.7 (2)
C3—C2—C7—N2	−179.69 (16)	O7—C16—C17—C22	22.0 (3)
N1—C2—C7—N2	−1.7 (2)	N4—C16—C17—C22	−159.06 (17)
C8—N2—C7—C6	85.3 (2)	C22—C17—C18—C19	−0.3 (3)
C8—N2—C7—C2	−96.4 (2)	C16—C17—C18—C19	174.92 (17)
C7—N2—C8—N4	170.75 (15)	C17—C18—C19—C20	0.4 (3)
C7—N2—C8—S2	−6.4 (2)	C18—C19—C20—C21	−0.3 (3)
C16—N4—C8—N2	−5.1 (3)	C19—C20—C21—C22	0.1 (4)
C16—N4—C8—S2	172.23 (14)	C20—C21—C22—C17	0.0 (4)
C1—N3—C9—O6	−1.2 (3)	C18—C17—C22—C21	0.1 (3)
C1—N3—C9—C10	178.76 (15)	C16—C17—C22—C21	−175.32 (19)
O6—C9—C10—C15	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O6	0.88	1.88	2.633 (2)	141.8
N2—HN2···O7	0.88	1.99	2.680 (2)	133.9
N4—HN4···S2i	0.88	2.61	3.478 (2)	169.9

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O6	0.88	1.88	2.633 (2)	142
N2—HN2⋯O7	0.88	1.99	2.680 (2)	134
N4—HN4⋯S2i	0.88	2.61	3.478 (2)	170

Symmetry code: (i) .