1,2-Bis[N'-(2,2-dimethyl-propionyl)thio-ureido]cyclo-hexa-ne.

In the title compound, C(18)H(32)N(4)O(2)S(2), the dihedral angle between the two thio-urea groups is 78.55 (7)°. The mol-ecular conformation is stabilized by intra-molecular N-H⋯O hydrogen bonds and the crystal structure is stabilized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For related crystal structures, see: Thiam et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H32N4O2S2

M = 400.60

Monoclinic,

a = 10.960 (2) Å

b = 19.065 (4) Å

c = 10.378 (2) Å

β = 96.112 (4)°

V = 2156.1 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 298 (2) K

0.48 × 0.41 × 0.37 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.883, T max = 0.908

10928 measured reflections

3779 independent reflections

2828 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.07

3779 reflections

241 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011495/bt2701sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011495/bt2701Isup2.hkl

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

C18H32N4O2S2	F000 = 864
Mr = 400.60	Dx = 1.234 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 982 reflections
a = 10.960 (2) Å	θ = 1.9–25.0º
b = 19.065 (4) Å	µ = 0.27 mm−1
c = 10.378 (2) Å	T = 298 (2) K
β = 96.112 (4)º	Block, colourless
V = 2156.1 (8) Å3	0.48 × 0.41 × 0.37 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3779 independent reflections
Radiation source: fine-focus sealed tube	2828 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
Detector resolution: 83.66 pixels mm-1	θmax = 25.0º
T = 298(2) K	θmin = 1.9º
ω scans	h = −9→13
Absorption correction: multi-scan(SADABS; Bruker, 2000)	k = −22→22
Tmin = 0.883, Tmax = 0.908	l = −12→11
10928 measured 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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0662P)2 + 0.3145P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3779 reflections	Δρmax = 0.30 e Å−3
241 parameters	Δρmin = −0.22 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	0.12804 (6)	0.05301 (3)	−0.07986 (6)	0.0544 (2)
S2	0.03271 (6)	0.10826 (4)	0.56450 (6)	0.0689 (2)
O1	0.26724 (16)	−0.05371 (8)	0.29928 (15)	0.0566 (4)
O2	−0.21983 (13)	0.10785 (8)	0.19001 (14)	0.0464 (4)
N1	0.20717 (16)	−0.04742 (8)	0.08323 (17)	0.0424 (4)
H1	0.1996	−0.0721	0.0135	0.051*
N2	0.18658 (16)	0.06134 (8)	0.17475 (17)	0.0426 (4)
H2	0.2023	0.0397	0.2473	0.051*
N3	0.00442 (15)	0.13012 (9)	0.31031 (18)	0.0435 (4)
H3	−0.0426	0.1273	0.2387	0.052*
N4	−0.15887 (16)	0.08040 (10)	0.39865 (18)	0.0481 (5)
H4	−0.1840	0.0617	0.4664	0.058*
C1	0.1676 (3)	−0.19515 (13)	0.0914 (3)	0.0723 (8)
H1A	0.1771	−0.2452	0.0940	0.108*
H1B	0.1685	−0.1790	0.0039	0.108*
H1C	0.0910	−0.1827	0.1222	0.108*
C2	0.2729 (2)	−0.16111 (11)	0.1774 (2)	0.0468 (5)
C3	0.24848 (19)	−0.08288 (11)	0.1939 (2)	0.0415 (5)
C4	0.17546 (18)	0.02355 (11)	0.0674 (2)	0.0396 (5)
C5	0.17396 (18)	0.13730 (10)	0.1781 (2)	0.0391 (5)
H5	0.1138	0.1516	0.1063	0.047*
C6	0.2965 (2)	0.17181 (11)	0.1603 (2)	0.0462 (5)
H6A	0.3591	0.1529	0.2239	0.055*
H6B	0.3190	0.1603	0.0749	0.055*
C7	0.2932 (2)	0.25092 (11)	0.1746 (2)	0.0523 (6)
H7A	0.3743	0.2701	0.1682	0.063*
H7B	0.2375	0.2708	0.1053	0.063*
C8	0.2512 (2)	0.27047 (12)	0.3043 (2)	0.0564 (6)
H8A	0.3100	0.2534	0.3736	0.068*
H8B	0.2469	0.3211	0.3115	0.068*
C9	0.1265 (2)	0.23904 (11)	0.3176 (2)	0.0480 (6)
H9A	0.0671	0.2586	0.2513	0.058*
H9B	0.1014	0.2516	0.4014	0.058*
C10	0.12704 (18)	0.15951 (10)	0.3048 (2)	0.0396 (5)
H10	0.1819	0.1401	0.3767	0.048*
C11	−0.03989 (18)	0.10766 (11)	0.4159 (2)	0.0421 (5)
C12	−0.24141 (18)	0.07907 (11)	0.2897 (2)	0.0387 (5)
C13	−0.36266 (19)	0.04254 (11)	0.3039 (2)	0.0436 (5)
C14	−0.3419 (2)	−0.03052 (14)	0.3627 (3)	0.0676 (8)
H14A	−0.4196	−0.0533	0.3662	0.101*
H14B	−0.3006	−0.0265	0.4487	0.101*
H14C	−0.2926	−0.0577	0.3101	0.101*
C15	0.3909 (2)	−0.16947 (14)	0.1128 (3)	0.0769 (9)
H15A	0.4573	−0.1469	0.1647	0.115*
H15B	0.3805	−0.1484	0.0283	0.115*
H15C	0.4091	−0.2184	0.1047	0.115*
C16	0.2847 (4)	−0.19545 (14)	0.3097 (3)	0.1025 (13)
H16A	0.3535	−0.1757	0.3624	0.154*
H16B	0.2971	−0.2450	0.3004	0.154*
H16C	0.2112	−0.1875	0.3502	0.154*
C17	−0.4349 (2)	0.03560 (15)	0.1708 (2)	0.0607 (7)
H17A	−0.4482	0.0813	0.1330	0.091*
H17B	−0.5126	0.0138	0.1795	0.091*
H17C	−0.3895	0.0073	0.1161	0.091*
C18	−0.4344 (2)	0.08752 (15)	0.3912 (3)	0.0649 (7)
H18A	−0.4380	0.1349	0.3598	0.097*
H18B	−0.3941	0.0866	0.4780	0.097*
H18C	−0.5161	0.0693	0.3907	0.097*

	U11	U22	U33	U12	U13	U23
S1	0.0754 (4)	0.0458 (4)	0.0412 (3)	0.0087 (3)	0.0030 (3)	0.0069 (3)
S2	0.0585 (4)	0.0989 (6)	0.0462 (4)	−0.0190 (4)	−0.0089 (3)	0.0110 (3)
O1	0.0847 (12)	0.0408 (9)	0.0420 (10)	0.0074 (8)	−0.0043 (8)	−0.0010 (7)
O2	0.0466 (9)	0.0556 (9)	0.0366 (9)	−0.0066 (7)	0.0027 (6)	0.0042 (7)
N1	0.0578 (11)	0.0324 (9)	0.0363 (10)	0.0027 (8)	0.0014 (8)	−0.0020 (8)
N2	0.0563 (11)	0.0337 (9)	0.0376 (10)	0.0042 (8)	0.0039 (8)	0.0023 (8)
N3	0.0363 (9)	0.0525 (11)	0.0411 (11)	−0.0040 (8)	0.0011 (8)	−0.0005 (8)
N4	0.0415 (10)	0.0599 (12)	0.0423 (11)	−0.0091 (9)	0.0012 (8)	0.0127 (9)
C1	0.0789 (19)	0.0417 (14)	0.096 (2)	−0.0145 (13)	0.0081 (16)	−0.0041 (14)
C2	0.0633 (15)	0.0318 (11)	0.0454 (13)	0.0014 (10)	0.0067 (11)	0.0026 (10)
C3	0.0472 (12)	0.0355 (11)	0.0416 (13)	−0.0012 (9)	0.0045 (10)	0.0017 (10)
C4	0.0414 (12)	0.0351 (11)	0.0431 (13)	0.0009 (9)	0.0080 (9)	0.0011 (9)
C5	0.0413 (11)	0.0320 (11)	0.0437 (12)	0.0075 (9)	0.0031 (9)	0.0018 (9)
C6	0.0430 (12)	0.0453 (12)	0.0514 (14)	0.0050 (10)	0.0094 (10)	−0.0004 (10)
C7	0.0501 (13)	0.0433 (13)	0.0645 (16)	−0.0060 (10)	0.0108 (11)	0.0003 (11)
C8	0.0619 (15)	0.0435 (13)	0.0646 (16)	−0.0077 (11)	0.0103 (12)	−0.0097 (12)
C9	0.0486 (13)	0.0422 (12)	0.0543 (14)	0.0061 (10)	0.0105 (11)	−0.0072 (11)
C10	0.0326 (11)	0.0402 (12)	0.0456 (13)	0.0005 (9)	0.0019 (9)	−0.0014 (10)
C11	0.0402 (12)	0.0401 (12)	0.0456 (13)	−0.0009 (9)	0.0025 (10)	0.0032 (10)
C12	0.0417 (12)	0.0366 (11)	0.0377 (12)	0.0042 (9)	0.0044 (9)	−0.0012 (9)
C13	0.0362 (11)	0.0522 (13)	0.0426 (13)	−0.0029 (10)	0.0058 (9)	0.0025 (10)
C14	0.0560 (15)	0.0608 (16)	0.086 (2)	−0.0131 (13)	0.0092 (14)	0.0163 (15)
C15	0.0644 (17)	0.0511 (15)	0.117 (3)	0.0140 (13)	0.0166 (17)	0.0041 (16)
C16	0.214 (4)	0.0405 (15)	0.0529 (18)	0.0181 (19)	0.011 (2)	0.0113 (13)
C17	0.0458 (13)	0.0868 (18)	0.0492 (15)	−0.0151 (13)	0.0037 (11)	−0.0059 (13)
C18	0.0494 (14)	0.088 (2)	0.0584 (17)	0.0067 (13)	0.0092 (12)	−0.0083 (14)

S1—C4	1.659 (2)	C7—C8	1.515 (3)
S2—C11	1.658 (2)	C7—H7A	0.9700
O1—C3	1.224 (2)	C7—H7B	0.9700
O2—C12	1.217 (2)	C8—C9	1.512 (3)
N1—C3	1.368 (3)	C8—H8A	0.9700
N1—C4	1.402 (3)	C8—H8B	0.9700
N1—H1	0.8600	C9—C10	1.522 (3)
N2—C4	1.322 (3)	C9—H9A	0.9700
N2—C5	1.455 (2)	C9—H9B	0.9700
N2—H2	0.8600	C10—H10	0.9800
N3—C11	1.317 (3)	C12—C13	1.521 (3)
N3—C10	1.463 (3)	C13—C17	1.522 (3)
N3—H3	0.8600	C13—C18	1.525 (3)
N4—C12	1.371 (3)	C13—C14	1.528 (3)
N4—C11	1.397 (3)	C14—H14A	0.9600
N4—H4	0.8600	C14—H14B	0.9600
C1—C2	1.526 (4)	C14—H14C	0.9600
C1—H1A	0.9600	C15—H15A	0.9600
C1—H1B	0.9600	C15—H15B	0.9600
C1—H1C	0.9600	C15—H15C	0.9600
C2—C16	1.514 (3)	C16—H16A	0.9600
C2—C15	1.528 (4)	C16—H16B	0.9600
C2—C3	1.528 (3)	C16—H16C	0.9600
C5—C10	1.522 (3)	C17—H17A	0.9600
C5—C6	1.524 (3)	C17—H17B	0.9600
C5—H5	0.9800	C17—H17C	0.9600
C6—C7	1.516 (3)	C18—H18A	0.9600
C6—H6A	0.9700	C18—H18B	0.9600
C6—H6B	0.9700	C18—H18C	0.9600
C3—N1—C4	129.13 (18)	C8—C9—C10	112.04 (18)
C3—N1—H1	115.4	C8—C9—H9A	109.2
C4—N1—H1	115.4	C10—C9—H9A	109.2
C4—N2—C5	124.21 (18)	C8—C9—H9B	109.2
C4—N2—H2	117.9	C10—C9—H9B	109.2
C5—N2—H2	117.9	H9A—C9—H9B	107.9
C11—N3—C10	125.39 (18)	N3—C10—C5	108.89 (16)
C11—N3—H3	117.3	N3—C10—C9	111.49 (16)
C10—N3—H3	117.3	C5—C10—C9	110.94 (17)
C12—N4—C11	129.61 (18)	N3—C10—H10	108.5
C12—N4—H4	115.2	C5—C10—H10	108.5
C11—N4—H4	115.2	C9—C10—H10	108.5
C2—C1—H1A	109.5	N3—C11—N4	115.86 (18)
C2—C1—H1B	109.5	N3—C11—S2	126.07 (16)
H1A—C1—H1B	109.5	N4—C11—S2	118.07 (16)
C2—C1—H1C	109.5	O2—C12—N4	121.47 (19)
H1A—C1—H1C	109.5	O2—C12—C13	122.65 (18)
H1B—C1—H1C	109.5	N4—C12—C13	115.82 (18)
C16—C2—C1	109.5 (2)	C12—C13—C17	109.11 (18)
C16—C2—C15	111.0 (2)	C12—C13—C18	108.09 (19)
C1—C2—C15	108.7 (2)	C17—C13—C18	109.67 (19)
C16—C2—C3	108.65 (19)	C12—C13—C14	111.20 (17)
C1—C2—C3	110.51 (19)	C17—C13—C14	108.9 (2)
C15—C2—C3	108.50 (18)	C18—C13—C14	109.9 (2)
O1—C3—N1	122.32 (19)	C13—C14—H14A	109.5
O1—C3—C2	121.91 (19)	C13—C14—H14B	109.5
N1—C3—C2	115.75 (18)	H14A—C14—H14B	109.5
N2—C4—N1	115.32 (18)	C13—C14—H14C	109.5
N2—C4—S1	125.71 (16)	H14A—C14—H14C	109.5
N1—C4—S1	118.96 (16)	H14B—C14—H14C	109.5
N2—C5—C10	109.84 (16)	C2—C15—H15A	109.5
N2—C5—C6	109.84 (16)	C2—C15—H15B	109.5
C10—C5—C6	111.57 (17)	H15A—C15—H15B	109.5
N2—C5—H5	108.5	C2—C15—H15C	109.5
C10—C5—H5	108.5	H15A—C15—H15C	109.5
C6—C5—H5	108.5	H15B—C15—H15C	109.5
C7—C6—C5	112.79 (17)	C2—C16—H16A	109.5
C7—C6—H6A	109.0	C2—C16—H16B	109.5
C5—C6—H6A	109.0	H16A—C16—H16B	109.5
C7—C6—H6B	109.0	C2—C16—H16C	109.5
C5—C6—H6B	109.0	H16A—C16—H16C	109.5
H6A—C6—H6B	107.8	H16B—C16—H16C	109.5
C8—C7—C6	110.14 (19)	C13—C17—H17A	109.5
C8—C7—H7A	109.6	C13—C17—H17B	109.5
C6—C7—H7A	109.6	H17A—C17—H17B	109.5
C8—C7—H7B	109.6	C13—C17—H17C	109.5
C6—C7—H7B	109.6	H17A—C17—H17C	109.5
H7A—C7—H7B	108.1	H17B—C17—H17C	109.5
C9—C8—C7	110.28 (19)	C13—C18—H18A	109.5
C9—C8—H8A	109.6	C13—C18—H18B	109.5
C7—C8—H8A	109.6	H18A—C18—H18B	109.5
C9—C8—H8B	109.6	C13—C18—H18C	109.5
C7—C8—H8B	109.6	H18A—C18—H18C	109.5
H8A—C8—H8B	108.1	H18B—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.97	2.650 (2)	135
N3—H3···O2	0.86	1.99	2.670 (2)	135
N1—H1···O2i	0.86	2.25	3.078 (2)	161
C1—H1B···O2i	0.96	2.54	3.462 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.97	2.650 (2)	135
N3—H3⋯O2	0.86	1.99	2.670 (2)	135
N1—H1⋯O2i	0.86	2.25	3.078 (2)	161
C1—H1B⋯O2i	0.96	2.54	3.462 (3)	161

Symmetry code: (i) .