3,3'-Dibutanoyl-1,1'-(o-phenyl-ene)dithio-urea.

The mol-ecular conformation of the title compound, C(16)H(22)N(4)O(2)S(2), is stabilized by two intramolecular N-H⋯O hydrogen bonds. The crystal packing shows N-H⋯O and N-H⋯S hydrogen bonds.

Related literature

For details of the biological activity of bisthio­ureas, see: Berkessel et al. (2006 ▶); Moloto et al. (2004 ▶). For their applications, see: Atia et al. (2005 ▶); Hu et al. (2009 ▶); Phetsuksiri et al. (2003 ▶). For the synthesis of the title compound, see: Succaw et al. (2005 ▶).

Experimental

Crystal data

C16H22N4O2S2

M = 366.50

Monoclinic,

a = 8.8099 (5) Å

b = 16.4925 (7) Å

c = 12.3923 (8) Å

β = 91.949 (5)°

V = 1799.53 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 173 K

0.28 × 0.28 × 0.23 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.918, T max = 0.932

22483 measured reflections

3360 independent reflections

2890 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.095

S = 1.04

3360 reflections

229 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.33 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA (Stoe & Cie, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001789/bg2318sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001789/bg2318Isup2.hkl

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

C16H22N4O2S2	F(000) = 776
Mr = 366.50	Dx = 1.353 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 20465 reflections
a = 8.8099 (5) Å	θ = 3.4–26.0°
b = 16.4925 (7) Å	µ = 0.31 mm−1
c = 12.3923 (8) Å	T = 173 K
β = 91.949 (5)°	Block, colourless
V = 1799.53 (17) Å3	0.28 × 0.28 × 0.23 mm
Z = 4

Stoe IPDS II two-circle diffractometer	3360 independent reflections
Radiation source: fine-focus sealed tube	2890 reflections with I > 2σ(I)
graphite	Rint = 0.087
ω scans	θmax = 25.6°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −10→10
Tmin = 0.918, Tmax = 0.932	k = −19→18
22483 measured reflections	l = −15→14

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.139P] where P = (Fo2 + 2Fc2)/3
3360 reflections	(Δ/σ)max = 0.001
229 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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	0.07444 (5)	0.68569 (3)	0.35994 (3)	0.02446 (14)
S2	0.47542 (5)	0.79179 (3)	0.52094 (3)	0.02947 (14)
O1	0.38901 (14)	0.53284 (9)	0.57778 (9)	0.0278 (3)
O2	0.83408 (13)	0.59749 (8)	0.58037 (9)	0.0224 (3)
C1	0.42857 (18)	0.65251 (9)	0.31239 (12)	0.0152 (3)
C2	0.57714 (18)	0.67920 (9)	0.33537 (12)	0.0154 (3)
C3	0.66576 (19)	0.70843 (10)	0.25383 (13)	0.0206 (3)
H3	0.7674	0.7249	0.2695	0.025*
C4	0.6054 (2)	0.71355 (11)	0.14871 (13)	0.0228 (4)
H4	0.6654	0.7342	0.0927	0.027*
C5	0.4579 (2)	0.68847 (10)	0.12589 (12)	0.0211 (4)
H5	0.4170	0.6924	0.0542	0.025*
C6	0.36860 (19)	0.65746 (10)	0.20698 (12)	0.0180 (3)
H6	0.2678	0.6399	0.1906	0.022*
N11	0.34909 (15)	0.61572 (8)	0.39740 (10)	0.0160 (3)
H11	0.401 (2)	0.5867 (12)	0.4430 (16)	0.019*
C11	0.20588 (17)	0.62849 (10)	0.42462 (12)	0.0159 (3)
N12	0.16371 (16)	0.58921 (8)	0.51872 (10)	0.0168 (3)
H12	0.072 (2)	0.5945 (12)	0.5357 (15)	0.020*
C12	0.25388 (19)	0.54519 (10)	0.59085 (12)	0.0195 (3)
C13	0.1723 (2)	0.51260 (12)	0.68687 (14)	0.0272 (4)
H13A	0.1316	0.4581	0.6691	0.033*
H13B	0.0852	0.5484	0.7017	0.033*
C14	0.2751 (2)	0.50692 (12)	0.78795 (14)	0.0285 (4)
H14A	0.2206	0.4776	0.8446	0.034*
H14B	0.3663	0.4748	0.7711	0.034*
C15	0.3251 (3)	0.58888 (14)	0.83166 (17)	0.0447 (5)
H15A	0.3912	0.5812	0.8961	0.054*
H15B	0.2357	0.6205	0.8506	0.054*
H15C	0.3809	0.6179	0.7765	0.054*
N21	0.64067 (16)	0.67101 (9)	0.44277 (10)	0.0170 (3)
H21	0.708 (2)	0.6374 (13)	0.4558 (15)	0.020*
C21	0.59630 (17)	0.71486 (10)	0.52676 (12)	0.0171 (3)
N22	0.65944 (15)	0.69253 (8)	0.62711 (11)	0.0172 (3)
H22	0.630 (2)	0.7231 (13)	0.6794 (16)	0.021*
C22	0.77077 (18)	0.63670 (10)	0.65070 (12)	0.0178 (3)
C23	0.8064 (2)	0.62499 (11)	0.76915 (12)	0.0223 (4)
H23A	0.7462	0.6636	0.8114	0.027*
H23B	0.9154	0.6361	0.7847	0.027*
C24	0.7692 (2)	0.53829 (12)	0.80244 (14)	0.0308 (4)
H24A	0.6617	0.5264	0.7825	0.037*
H24B	0.8335	0.5000	0.7627	0.037*
C25	0.7954 (4)	0.52563 (15)	0.92284 (17)	0.0580 (8)
H25A	0.7694	0.4697	0.9415	0.070*
H25B	0.7314	0.5632	0.9623	0.070*
H25C	0.9024	0.5358	0.9424	0.070*

	U11	U22	U33	U12	U13	U23
S1	0.0188 (2)	0.0308 (3)	0.0237 (2)	0.00497 (16)	0.00078 (16)	0.01004 (17)
S2	0.0334 (3)	0.0301 (3)	0.0245 (2)	0.01694 (19)	−0.00509 (18)	−0.00387 (18)
O1	0.0216 (6)	0.0399 (8)	0.0223 (6)	0.0105 (5)	0.0046 (5)	0.0104 (5)
O2	0.0225 (6)	0.0264 (7)	0.0184 (6)	0.0085 (5)	−0.0012 (4)	−0.0018 (5)
C1	0.0168 (7)	0.0135 (8)	0.0153 (7)	0.0021 (6)	0.0025 (6)	0.0011 (6)
C2	0.0181 (8)	0.0137 (8)	0.0144 (7)	0.0028 (6)	−0.0005 (6)	−0.0001 (6)
C3	0.0182 (8)	0.0201 (9)	0.0236 (8)	0.0003 (6)	0.0022 (6)	0.0020 (6)
C4	0.0268 (9)	0.0219 (9)	0.0200 (8)	0.0017 (7)	0.0073 (6)	0.0058 (7)
C5	0.0289 (9)	0.0213 (9)	0.0130 (7)	0.0052 (7)	0.0006 (6)	0.0007 (6)
C6	0.0191 (8)	0.0172 (8)	0.0175 (7)	0.0012 (6)	−0.0026 (6)	−0.0011 (6)
N11	0.0152 (6)	0.0189 (7)	0.0138 (6)	0.0005 (5)	−0.0007 (5)	0.0040 (5)
C11	0.0175 (8)	0.0155 (8)	0.0145 (7)	−0.0034 (6)	−0.0010 (6)	−0.0020 (6)
N12	0.0137 (7)	0.0200 (7)	0.0168 (6)	0.0006 (5)	0.0021 (5)	0.0035 (5)
C12	0.0216 (8)	0.0201 (8)	0.0169 (7)	0.0026 (6)	0.0017 (6)	0.0010 (6)
C13	0.0256 (9)	0.0324 (10)	0.0242 (8)	0.0047 (7)	0.0063 (7)	0.0108 (7)
C14	0.0391 (10)	0.0280 (10)	0.0187 (8)	0.0083 (8)	0.0043 (7)	0.0074 (7)
C15	0.0663 (16)	0.0377 (12)	0.0303 (10)	0.0012 (11)	0.0033 (10)	−0.0059 (9)
N21	0.0153 (7)	0.0195 (7)	0.0159 (6)	0.0045 (5)	−0.0027 (5)	−0.0006 (5)
C21	0.0147 (7)	0.0185 (8)	0.0180 (7)	−0.0001 (6)	0.0001 (6)	0.0006 (6)
N22	0.0190 (7)	0.0177 (7)	0.0148 (6)	0.0015 (5)	−0.0010 (5)	−0.0029 (5)
C22	0.0186 (8)	0.0168 (8)	0.0178 (7)	−0.0021 (6)	−0.0028 (6)	0.0003 (6)
C23	0.0296 (9)	0.0203 (9)	0.0167 (8)	0.0036 (7)	−0.0047 (6)	−0.0010 (6)
C24	0.0442 (11)	0.0265 (10)	0.0215 (8)	−0.0072 (8)	0.0001 (8)	0.0024 (7)
C25	0.115 (2)	0.0344 (13)	0.0240 (10)	−0.0185 (14)	−0.0110 (12)	0.0085 (9)

S1—C11	1.6763 (16)	C13—H13A	0.9900
S2—C21	1.6566 (16)	C13—H13B	0.9900
O1—C12	1.224 (2)	C14—C15	1.516 (3)
O2—C22	1.234 (2)	C14—H14A	0.9900
C1—C6	1.395 (2)	C14—H14B	0.9900
C1—C2	1.401 (2)	C15—H15A	0.9800
C1—N11	1.4207 (19)	C15—H15B	0.9800
C2—C3	1.385 (2)	C15—H15C	0.9800
C2—N21	1.4325 (19)	N21—C21	1.337 (2)
C3—C4	1.393 (2)	N21—H21	0.83 (2)
C3—H3	0.9500	C21—N22	1.395 (2)
C4—C5	1.384 (3)	N22—C22	1.370 (2)
C4—H4	0.9500	N22—H22	0.87 (2)
C5—C6	1.394 (2)	C22—C23	1.503 (2)
C5—H5	0.9500	C23—C24	1.527 (3)
C6—H6	0.9500	C23—H23A	0.9900
N11—C11	1.334 (2)	C23—H23B	0.9900
N11—H11	0.86 (2)	C24—C25	1.516 (3)
C11—N12	1.395 (2)	C24—H24A	0.9900
N12—C12	1.382 (2)	C24—H24B	0.9900
N12—H12	0.84 (2)	C25—H25A	0.9800
C12—C13	1.510 (2)	C25—H25B	0.9800
C13—C14	1.524 (3)	C25—H25C	0.9800
C6—C1—C2	119.57 (14)	C15—C14—H14B	108.9
C6—C1—N11	122.61 (14)	C13—C14—H14B	108.9
C2—C1—N11	117.65 (13)	H14A—C14—H14B	107.7
C3—C2—C1	120.47 (14)	C14—C15—H15A	109.5
C3—C2—N21	119.91 (14)	C14—C15—H15B	109.5
C1—C2—N21	119.48 (14)	H15A—C15—H15B	109.5
C2—C3—C4	119.80 (15)	C14—C15—H15C	109.5
C2—C3—H3	120.1	H15A—C15—H15C	109.5
C4—C3—H3	120.1	H15B—C15—H15C	109.5
C5—C4—C3	119.94 (15)	C21—N21—C2	123.85 (14)
C5—C4—H4	120.0	C21—N21—H21	116.0 (13)
C3—C4—H4	120.0	C2—N21—H21	120.1 (13)
C4—C5—C6	120.74 (15)	N21—C21—N22	115.68 (14)
C4—C5—H5	119.6	N21—C21—S2	125.81 (12)
C6—C5—H5	119.6	N22—C21—S2	118.52 (12)
C5—C6—C1	119.45 (15)	C22—N22—C21	128.97 (14)
C5—C6—H6	120.3	C22—N22—H22	117.5 (13)
C1—C6—H6	120.3	C21—N22—H22	113.1 (13)
C11—N11—C1	127.91 (14)	O2—C22—N22	122.64 (14)
C11—N11—H11	114.1 (12)	O2—C22—C23	122.56 (15)
C1—N11—H11	117.4 (13)	N22—C22—C23	114.77 (14)
N11—C11—N12	114.78 (14)	C22—C23—C24	110.15 (14)
N11—C11—S1	127.73 (12)	C22—C23—H23A	109.6
N12—C11—S1	117.49 (11)	C24—C23—H23A	109.6
C12—N12—C11	128.39 (14)	C22—C23—H23B	109.6
C12—N12—H12	115.2 (13)	C24—C23—H23B	109.6
C11—N12—H12	116.3 (13)	H23A—C23—H23B	108.1
O1—C12—N12	122.84 (14)	C25—C24—C23	111.58 (16)
O1—C12—C13	122.44 (15)	C25—C24—H24A	109.3
N12—C12—C13	114.71 (14)	C23—C24—H24A	109.3
C12—C13—C14	112.57 (15)	C25—C24—H24B	109.3
C12—C13—H13A	109.1	C23—C24—H24B	109.3
C14—C13—H13A	109.1	H24A—C24—H24B	108.0
C12—C13—H13B	109.1	C24—C25—H25A	109.5
C14—C13—H13B	109.1	C24—C25—H25B	109.5
H13A—C13—H13B	107.8	H25A—C25—H25B	109.5
C15—C14—C13	113.35 (16)	C24—C25—H25C	109.5
C15—C14—H14A	108.9	H25A—C25—H25C	109.5
C13—C14—H14A	108.9	H25B—C25—H25C	109.5
C6—C1—C2—C3	−1.7 (2)	C11—N12—C12—O1	−2.4 (3)
N11—C1—C2—C3	173.81 (15)	C11—N12—C12—C13	178.22 (16)
C6—C1—C2—N21	−177.47 (14)	O1—C12—C13—C14	31.9 (2)
N11—C1—C2—N21	−2.0 (2)	N12—C12—C13—C14	−148.67 (15)
C1—C2—C3—C4	1.9 (2)	C12—C13—C14—C15	67.2 (2)
N21—C2—C3—C4	177.67 (15)	C3—C2—N21—C21	113.70 (18)
C2—C3—C4—C5	−0.8 (3)	C1—C2—N21—C21	−70.5 (2)
C3—C4—C5—C6	−0.4 (3)	C2—N21—C21—N22	173.38 (14)
C4—C5—C6—C1	0.6 (2)	C2—N21—C21—S2	−6.7 (2)
C2—C1—C6—C5	0.4 (2)	N21—C21—N22—C22	6.5 (2)
N11—C1—C6—C5	−174.83 (15)	S2—C21—N22—C22	−173.42 (13)
C6—C1—N11—C11	−49.1 (2)	C21—N22—C22—O2	1.0 (3)
C2—C1—N11—C11	135.57 (16)	C21—N22—C22—C23	−177.18 (15)
C1—N11—C11—N12	−174.00 (14)	O2—C22—C23—C24	−61.4 (2)
C1—N11—C11—S1	5.6 (2)	N22—C22—C23—C24	116.77 (17)
N11—C11—N12—C12	6.0 (2)	C22—C23—C24—C25	−176.8 (2)
S1—C11—N12—C12	−173.65 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O1	0.86 (2)	1.90 (2)	2.6336 (17)	142.6 (17)
N12—H12···O2i	0.84 (2)	2.19 (2)	3.0309 (18)	175.3 (19)
N21—H21···O2	0.83 (2)	1.98 (2)	2.6616 (18)	139.1 (18)
N22—H22···S1ii	0.87 (2)	2.75 (2)	3.6147 (14)	172.0 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O1	0.86 (2)	1.90 (2)	2.6336 (17)	142.6 (17)
N12—H12⋯O2i	0.84 (2)	2.19 (2)	3.0309 (18)	175.3 (19)
N21—H21⋯O2	0.83 (2)	1.98 (2)	2.6616 (18)	139.1 (18)
N22—H22⋯S1ii	0.87 (2)	2.75 (2)	3.6147 (14)	172.0 (17)

Symmetry codes: (i) ; (ii) .