N-(N-Benzoyl­hydrazinocarbo­thio­yl)­benz­amide

The molecular structure of the title compound, C₁₅H₁₃N₃O₂S, adopts a cis–trans configuration with respect to the position of the benzoyl and benz­amide groups relative to the S atom across the thio­urea C—N bonds, respectively. In the crystal structure, the mol­ecules are linked by weak N—H...O and C—H...O interactions into linear chains parallel to the c axis.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.057
• wR factor = 0.133
• Data-to-parameter ratio = 16.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

The molecular structure and dimension of the title compound, (I), is similar to other benzoylthiourea derivatives, such as in N-benzoyl-N'-phenylthiourea (Yamin & Yusof, 2003a), N-benzoyl-N'-(3,4-dimethylphenyl)thiourea (Shanmuga Sundara Raj et al., 1999), N'-benzoyl-N-p-bromophenylthiourea (Yamin & Yusof, 2003b) with a cis–trans configuration with respect to the position of the benzamide and benzoyl groups relative to the S atom across the C8—N2 and C8—N1 bonds, respectively.

The central carbonyl–thiourea moiety (S1/C8/N1/N2) is planar. The benzoyl [maximum deviation at O1 of 0.348 (2) Å] and benzamide [maximum deviation at N3 of 0.306 (2) Å] fragments are essentially planar. The central thiourea moeity makes angles with the benzoyl and benzamide fragments of 15.12 (11) and 31.45 (12)°, respectively. The inclination between the benzoyl and benzamide fragments is 16.42 (14)°. There are two N—H···O and N—H···S intramolecular hydrogen bonds (Table 2). In the crystal structure, the molecules are linked by intermolecular N—H···O and C—H···O contacts (Table 2), forming linear chains parallel to the c axis (Fig. 2).

S2. Experimental

A solution of benzhydrazide (1.62 g, 0.011 mol) in acetone (50 ml) was added dropwise to 50 ml of an acetone solution containing an equimolar amount of benzoylisothiocyanate in a two-necked round-bottomed flask. The solution was refluxed for about 2 h and then cooled in ice. The white precipitate was filtered off and washed with ethanol-distilled water, then dried in a vacuum (yield 83%). Recrystallization from ethanol yielded single crystals suitable for X-ray analysis.

S3. Refinement

After checking their presence in the difference map, all H atoms were fixed geometrically and allowed to ride on the parent C or N atoms, with C—H = 0.93 Å and N—H = 0.86 Å.

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 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures

	Fig. 1. The molecular structure of (I), with 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of (I), viewed down the b axis. The dashed lines denote the N—H···O and C—H···O hydrogen bonds.

N-(N-Benzoyl-hydrazinocarbothioyl)-benzamide

Crystal data

C15H13N3O2S	F(000) = 624
Mr = 299.34	Dx = 1.412 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.7949 (19) Å	Cell parameters from 1584 reflections
b = 7.7004 (10) Å	θ = 1.6–27.5°
c = 13.9577 (18) Å	µ = 0.24 mm^−1
β = 117.705 (2)°	T = 273 K
V = 1407.8 (3) Å^3	Slab, colourless
Z = 4	0.55 × 0.21 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3097 independent reflections
Radiation source: fine-focus sealed tube	1925 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 83.66 pixels mm^-1	θmax = 27.5°, θmin = 1.6°
ω scans	h = −17→18
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
Tmin = 0.880, Tmax = 0.977	l = −18→13
7907 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0304P)^2 + 0.1794P] where P = (Fo^2 + 2Fc^2)/3
3097 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.19008 (5)	0.07097 (11)	0.41368 (6)	0.0628 (3)
O1	0.49547 (13)	0.1887 (3)	0.43281 (15)	0.0610 (5)
O2	0.30605 (14)	0.0778 (3)	0.13136 (15)	0.0602 (6)
N1	0.37856 (14)	0.1982 (3)	0.49423 (16)	0.0427 (5)
H1A	0.3677	0.2337	0.5464	0.051*
N2	0.31213 (15)	0.0790 (3)	0.32451 (17)	0.0474 (6)
H2A	0.3688	0.1062	0.3251	0.057*
N3	0.23692 (16)	−0.0041 (3)	0.23624 (17)	0.0513 (6)
H3A	0.1896	−0.0601	0.2424	0.062*
C1	0.54332 (19)	0.3085 (3)	0.7024 (2)	0.0487 (7)
H1B	0.4880	0.2551	0.7049	0.058*
C2	0.61817 (19)	0.3866 (4)	0.7941 (2)	0.0519 (7)
H2B	0.6133	0.3848	0.8582	0.062*
C3	0.6996 (2)	0.4668 (3)	0.7912 (2)	0.0503 (7)
H3B	0.7492	0.5213	0.8527	0.060*
C4	0.7076 (2)	0.4663 (4)	0.6969 (2)	0.0542 (7)
H4A	0.7630	0.5202	0.6950	0.065*
C5	0.63453 (19)	0.3868 (3)	0.6054 (2)	0.0479 (7)
H5A	0.6414	0.3850	0.5425	0.057*
C6	0.55034 (17)	0.3092 (3)	0.6068 (2)	0.0398 (6)
C7	0.47454 (18)	0.2282 (3)	0.5049 (2)	0.0430 (6)
C8	0.29731 (18)	0.1172 (3)	0.4087 (2)	0.0420 (6)
C9	0.23762 (19)	0.0024 (3)	0.1402 (2)	0.0432 (6)
C10	0.15052 (18)	−0.0874 (3)	0.0494 (2)	0.0410 (6)
C11	0.1361 (2)	−0.0548 (4)	−0.0539 (2)	0.0554 (7)
H11A	0.1808	0.0186	−0.0642	0.067*
C12	0.0556 (2)	−0.1308 (4)	−0.1423 (2)	0.0662 (9)
H12A	0.0465	−0.1087	−0.2118	0.079*
C13	−0.0104 (2)	−0.2379 (4)	−0.1279 (3)	0.0605 (8)
H13A	−0.0646	−0.2883	−0.1875	0.073*
C14	0.0029 (2)	−0.2711 (4)	−0.0262 (3)	0.0599 (8)
H14A	−0.0423	−0.3442	−0.0166	0.072*
C15	0.0835 (2)	−0.1964 (3)	0.0630 (2)	0.0531 (7)
H15A	0.0924	−0.2199	0.1322	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0491 (4)	0.0989 (6)	0.0431 (5)	−0.0197 (4)	0.0236 (4)	−0.0082 (4)
O1	0.0516 (11)	0.0927 (15)	0.0472 (12)	−0.0114 (10)	0.0302 (10)	−0.0224 (11)
O2	0.0541 (11)	0.0819 (14)	0.0466 (12)	−0.0176 (10)	0.0250 (10)	−0.0064 (10)
N1	0.0416 (11)	0.0568 (13)	0.0318 (12)	−0.0026 (9)	0.0189 (10)	−0.0048 (10)
N2	0.0425 (11)	0.0610 (14)	0.0384 (13)	−0.0084 (10)	0.0186 (10)	−0.0088 (11)
N3	0.0505 (13)	0.0657 (14)	0.0382 (14)	−0.0157 (11)	0.0209 (11)	−0.0105 (11)
C1	0.0424 (14)	0.0644 (18)	0.0448 (17)	−0.0046 (12)	0.0249 (13)	−0.0025 (13)
C2	0.0512 (16)	0.0726 (19)	0.0340 (15)	−0.0008 (14)	0.0216 (14)	−0.0049 (13)
C3	0.0478 (15)	0.0590 (17)	0.0382 (16)	−0.0030 (12)	0.0150 (13)	−0.0081 (13)
C4	0.0461 (15)	0.0690 (19)	0.0501 (18)	−0.0121 (13)	0.0246 (14)	−0.0035 (14)
C5	0.0490 (15)	0.0617 (17)	0.0383 (15)	−0.0042 (13)	0.0248 (13)	−0.0018 (13)
C6	0.0384 (13)	0.0452 (14)	0.0356 (14)	0.0029 (10)	0.0171 (12)	−0.0001 (11)
C7	0.0412 (13)	0.0516 (15)	0.0396 (16)	0.0008 (11)	0.0216 (13)	−0.0009 (12)
C8	0.0453 (14)	0.0478 (15)	0.0326 (14)	0.0015 (11)	0.0178 (12)	0.0012 (11)
C9	0.0452 (14)	0.0465 (15)	0.0374 (15)	0.0031 (11)	0.0187 (13)	−0.0011 (12)
C10	0.0413 (13)	0.0445 (14)	0.0372 (15)	0.0029 (11)	0.0182 (12)	−0.0032 (12)
C11	0.0553 (16)	0.071 (2)	0.0427 (18)	−0.0040 (14)	0.0255 (14)	−0.0066 (14)
C12	0.0666 (19)	0.089 (2)	0.0397 (18)	−0.0009 (17)	0.0220 (16)	−0.0145 (16)
C13	0.0503 (16)	0.0607 (19)	0.055 (2)	0.0006 (14)	0.0115 (15)	−0.0169 (15)
C14	0.0500 (16)	0.0540 (18)	0.067 (2)	−0.0053 (13)	0.0204 (16)	−0.0027 (15)
C15	0.0535 (16)	0.0558 (17)	0.0482 (18)	−0.0014 (13)	0.0220 (14)	0.0016 (14)

Geometric parameters (Å, º)

S1—C8	1.659 (3)	C4—C5	1.375 (4)
O1—C7	1.221 (3)	C4—H4A	0.9300
O2—C9	1.222 (3)	C5—C6	1.390 (3)
N1—C7	1.376 (3)	C5—H5A	0.9300
N1—C8	1.388 (3)	C6—C7	1.479 (3)
N1—H1A	0.8600	C9—C10	1.493 (3)
N2—C8	1.324 (3)	C10—C15	1.378 (3)
N2—N3	1.375 (3)	C10—C11	1.379 (4)
N2—H2A	0.8600	C11—C12	1.385 (4)
N3—C9	1.346 (3)	C11—H11A	0.9300
N3—H3A	0.8600	C12—C13	1.362 (4)
C1—C2	1.381 (3)	C12—H12A	0.9300
C1—C6	1.385 (3)	C13—C14	1.364 (4)
C1—H1B	0.9300	C13—H13A	0.9300
C2—C3	1.371 (3)	C14—C15	1.387 (4)
C2—H2B	0.9300	C14—H14A	0.9300
C3—C4	1.376 (4)	C15—H15A	0.9300
C3—H3B	0.9300
C7—N1—C8	127.3 (2)	O1—C7—N1	120.9 (2)
C7—N1—H1A	116.4	O1—C7—C6	121.9 (2)
C8—N1—H1A	116.4	N1—C7—C6	117.2 (2)
C8—N2—N3	120.0 (2)	N2—C8—N1	115.4 (2)
C8—N2—H2A	120.0	N2—C8—S1	123.08 (19)
N3—N2—H2A	120.0	N1—C8—S1	121.54 (19)
C9—N3—N2	119.8 (2)	O2—C9—N3	120.6 (2)
C9—N3—H3A	120.1	O2—C9—C10	124.2 (2)
N2—N3—H3A	120.1	N3—C9—C10	115.2 (2)
C2—C1—C6	120.2 (2)	C15—C10—C11	119.0 (2)
C2—C1—H1B	119.9	C15—C10—C9	123.8 (2)
C6—C1—H1B	119.9	C11—C10—C9	117.2 (2)
C3—C2—C1	120.4 (2)	C10—C11—C12	120.4 (3)
C3—C2—H2B	119.8	C10—C11—H11A	119.8
C1—C2—H2B	119.8	C12—C11—H11A	119.8
C2—C3—C4	119.7 (2)	C13—C12—C11	120.2 (3)
C2—C3—H3B	120.2	C13—C12—H12A	119.9
C4—C3—H3B	120.2	C11—C12—H12A	119.9
C5—C4—C3	120.6 (2)	C12—C13—C14	120.0 (3)
C5—C4—H4A	119.7	C12—C13—H13A	120.0
C3—C4—H4A	119.7	C14—C13—H13A	120.0
C4—C5—C6	120.1 (2)	C13—C14—C15	120.3 (3)
C4—C5—H5A	120.0	C13—C14—H14A	119.8
C6—C5—H5A	120.0	C15—C14—H14A	119.8
C1—C6—C5	119.0 (2)	C10—C15—C14	120.1 (3)
C1—C6—C7	124.2 (2)	C10—C15—H15A	119.9
C5—C6—C7	116.8 (2)	C14—C15—H15A	119.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.88	2.558 (3)	134
N3—H3A···S1	0.86	2.59	2.923 (2)	104
N1—H1A···O2^i	0.86	2.31	3.114 (3)	155
C2—H2B···O1^i	0.93	2.47	3.263 (4)	142

Symmetry code: (i) x, −y+1/2, z+1/2.