N,N′-Bis­(benz­amido­thio­carbonyl)­hydrazine di­methyl sulfoxide disolvate

In the title compound, C₁₆H₁₄N₄O₂S₂·2C₂H₆OS, the mol­ecule is discrete and centrosymmetric. The benzoyl­thiuourea and benzoyl groups are cis and trans, respectively, to the thio­urea S atom across the C—N bonds. In the crystal structure, the mol­ecule is linked to the solvent DMSO mol­ecules by N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
Some non-H atoms missing
• R factor = 0.055
• wR factor = 0.135
• Data-to-parameter ratio = 18.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



CHEMS_01  Alert A The sum formula contains more than one moiety.


 Alert Level B:



CHEMS_01  Alert B The sum formula contains an invalid character.
          WARNING - The character , is not allowed in the _chemical_formula_sum


 1 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

N,N'-Bis(benzamidothiocarbonyl)hydrazine dimethyl sulfoxide disolvate

Crystal data

C16H14N4O2S2·2C2H6OS	F(000) = 540
Mr = 514.70	Dx = 1.347 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.4127 (11) Å	Cell parameters from 1464 reflections
b = 15.486 (3) Å	θ = 2.1–27.5°
c = 12.805 (2) Å	µ = 0.41 mm^−1
β = 93.971 (3)°	T = 273 K
V = 1268.6 (4) Å^3	Block, colourless
Z = 2	0.56 × 0.34 × 0.33 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2862 independent reflections
Radiation source: fine-focus sealed tube	2008 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 83.66 pixels mm^-1	θmax = 27.5°, θmin = 2.1°
ω scans	h = −6→8
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −20→18
Tmin = 0.804, Tmax = 0.877	l = −16→16
7458 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0599P)^2 + 0.1638P] where P = (Fo^2 + 2Fc^2)/3
2862 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C8	0.1962 (4)	−0.02424 (15)	0.09943 (18)	0.0459 (6)
C7	0.4313 (4)	0.10169 (16)	0.12607 (19)	0.0494 (6)
C6	0.6199 (4)	0.13210 (15)	0.18956 (19)	0.0471 (6)
C5	0.6327 (5)	0.21923 (16)	0.2150 (2)	0.0606 (7)
H5	0.5233	0.2561	0.1940	0.073*
C4	0.8070 (5)	0.25130 (19)	0.2713 (2)	0.0671 (8)
H4	0.8134	0.3094	0.2896	0.081*
C3	0.9710 (5)	0.1975 (2)	0.3003 (2)	0.0671 (8)
H3	1.0902	0.2195	0.3363	0.081*
C2	0.9593 (5)	0.1108 (2)	0.2761 (2)	0.0633 (8)
H2	1.0701	0.0744	0.2964	0.076*
C1	0.7836 (4)	0.07799 (17)	0.2218 (2)	0.0525 (6)
H1	0.7751	0.0193	0.2069	0.063*
C9	−0.0485 (6)	0.3424 (2)	−0.0043 (3)	0.0917 (11)
H9A	−0.1850	0.3251	0.0140	0.137*
H9B	0.0168	0.2955	−0.0386	0.137*
H9C	−0.0608	0.3912	−0.0506	0.137*
C10	0.3287 (6)	0.4055 (3)	0.0486 (3)	0.0910 (11)
H10A	0.2898	0.4507	−0.0002	0.136*
H10B	0.3850	0.3577	0.0120	0.136*
H10C	0.4322	0.4267	0.1001	0.136*
N2	0.0878 (4)	0.01835 (15)	0.02432 (16)	0.0530 (6)
H2A	0.118 (4)	0.0642 (18)	0.006 (2)	0.054 (8)*
N1	0.3683 (3)	0.01850 (13)	0.14610 (17)	0.0487 (5)
H1A	0.418 (4)	−0.0048 (18)	0.202 (2)	0.068 (9)*
O1	0.3384 (3)	0.14790 (12)	0.06077 (16)	0.0712 (6)
O2	0.0077 (3)	0.45101 (12)	0.15261 (14)	0.0713 (6)
S1	0.13058 (13)	−0.12222 (4)	0.13923 (6)	0.0678 (3)
S2	0.10644 (12)	0.37118 (4)	0.11115 (5)	0.0561 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C8	0.0536 (15)	0.0403 (13)	0.0429 (13)	0.0017 (11)	−0.0022 (11)	0.0005 (10)
C7	0.0566 (16)	0.0453 (14)	0.0463 (14)	−0.0037 (12)	0.0029 (12)	0.0055 (11)
C6	0.0532 (15)	0.0431 (14)	0.0456 (13)	−0.0030 (12)	0.0073 (11)	0.0035 (11)
C5	0.0650 (18)	0.0435 (15)	0.0728 (18)	−0.0019 (13)	0.0016 (14)	0.0040 (13)
C4	0.076 (2)	0.0500 (17)	0.075 (2)	−0.0146 (15)	0.0021 (16)	−0.0044 (14)
C3	0.0613 (19)	0.073 (2)	0.0664 (18)	−0.0251 (16)	−0.0004 (14)	0.0035 (15)
C2	0.0495 (17)	0.073 (2)	0.0671 (18)	−0.0021 (14)	0.0007 (14)	0.0076 (15)
C1	0.0558 (17)	0.0441 (15)	0.0578 (15)	0.0008 (12)	0.0064 (13)	0.0008 (12)
C9	0.101 (3)	0.097 (3)	0.074 (2)	0.005 (2)	−0.020 (2)	−0.0299 (19)
C10	0.096 (3)	0.098 (3)	0.082 (2)	−0.007 (2)	0.025 (2)	−0.0033 (19)
N2	0.0658 (15)	0.0438 (13)	0.0472 (12)	−0.0099 (11)	−0.0117 (10)	0.0099 (10)
N1	0.0549 (13)	0.0424 (11)	0.0471 (12)	−0.0034 (10)	−0.0082 (10)	0.0076 (10)
O1	0.0814 (14)	0.0539 (11)	0.0747 (13)	−0.0139 (10)	−0.0206 (11)	0.0245 (10)
O2	0.0927 (16)	0.0657 (12)	0.0543 (11)	0.0232 (11)	−0.0032 (10)	−0.0146 (9)
S1	0.0825 (6)	0.0400 (4)	0.0764 (5)	−0.0093 (3)	−0.0256 (4)	0.0140 (3)
S2	0.0736 (5)	0.0477 (4)	0.0467 (4)	0.0033 (3)	0.0015 (3)	−0.0052 (3)

Geometric parameters (Å, º)

C8—N2	1.323 (3)	C2—H2	0.9300
C8—N1	1.386 (3)	C1—H1	0.9300
C8—S1	1.664 (2)	C9—S2	1.780 (3)
C7—O1	1.224 (3)	C9—H9A	0.9600
C7—N1	1.380 (3)	C9—H9B	0.9600
C7—C6	1.486 (4)	C9—H9C	0.9600
C6—C1	1.384 (3)	C10—S2	1.764 (3)
C6—C5	1.389 (3)	C10—H10A	0.9600
C5—C4	1.380 (4)	C10—H10B	0.9600
C5—H5	0.9300	C10—H10C	0.9600
C4—C3	1.372 (4)	N2—N2^i	1.372 (4)
C4—H4	0.9300	N2—H2A	0.78 (3)
C3—C2	1.379 (4)	N1—H1A	0.85 (3)
C3—H3	0.9300	O2—S2	1.5026 (19)
C2—C1	1.379 (4)
N2—C8—N1	116.0 (2)	C6—C1—H1	119.9
N2—C8—S1	123.1 (2)	S2—C9—H9A	109.5
N1—C8—S1	120.94 (18)	S2—C9—H9B	109.5
O1—C7—N1	122.5 (2)	H9A—C9—H9B	109.5
O1—C7—C6	121.9 (2)	S2—C9—H9C	109.5
N1—C7—C6	115.6 (2)	H9A—C9—H9C	109.5
C1—C6—C5	119.1 (2)	H9B—C9—H9C	109.5
C1—C6—C7	122.9 (2)	S2—C10—H10A	109.5
C5—C6—C7	118.0 (2)	S2—C10—H10B	109.5
C4—C5—C6	120.3 (3)	H10A—C10—H10B	109.5
C4—C5—H5	119.8	S2—C10—H10C	109.5
C6—C5—H5	119.8	H10A—C10—H10C	109.5
C3—C4—C5	120.0 (3)	H10B—C10—H10C	109.5
C3—C4—H4	120.0	C8—N2—N2^i	119.8 (3)
C5—C4—H4	120.0	C8—N2—H2A	123 (2)
C4—C3—C2	120.2 (3)	N2^i—N2—H2A	117 (2)
C4—C3—H3	119.9	C7—N1—C8	126.9 (2)
C2—C3—H3	119.9	C7—N1—H1A	117.1 (19)
C3—C2—C1	120.1 (3)	C8—N1—H1A	114.0 (19)
C3—C2—H2	120.0	O2—S2—C10	106.64 (16)
C1—C2—H2	120.0	O2—S2—C9	105.94 (15)
C2—C1—C6	120.3 (2)	C10—S2—C9	96.91 (19)
C2—C1—H1	119.9
O1—C7—C6—C1	−146.5 (3)	C3—C2—C1—C6	1.3 (4)
N1—C7—C6—C1	33.8 (3)	C5—C6—C1—C2	−1.7 (4)
O1—C7—C6—C5	31.9 (4)	C7—C6—C1—C2	176.7 (2)
N1—C7—C6—C5	−147.8 (2)	N1—C8—N2—N2^i	−178.4 (3)
C1—C6—C5—C4	0.3 (4)	S1—C8—N2—N2^i	0.1 (4)
C7—C6—C5—C4	−178.2 (3)	O1—C7—N1—C8	−1.1 (4)
C6—C5—C4—C3	1.6 (4)	C6—C7—N1—C8	178.6 (2)
C5—C4—C3—C2	−2.0 (4)	N2—C8—N1—C7	3.5 (4)
C4—C3—C2—C1	0.6 (4)	S1—C8—N1—C7	−175.1 (2)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.78 (3)	2.01 (3)	2.593 (3)	132 (2)
N2—H2A···S1^i	0.78 (3)	2.53 (3)	2.920 (2)	113 (2)
N1—H1A···O2^ii	0.84 (3)	2.01 (3)	2.843 (3)	169 (3)

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