organic compounds
1,2-Bis[N′-(2,2-dimethylpropionyl)thioureido]cyclohexane
aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Mengabang Telipot, 21030 Kuala Terengganu, Malaysia, and bSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
*Correspondence e-mail: mohdsukeri@umt.edu.my
In the title compound, C18H32N4O2S2, the dihedral angle between the two thiourea groups is 78.55 (7)°. The molecular conformation is stabilized by intramolecular N—H⋯O hydrogen bonds and the is stabilized by intermolecular 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
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Refinement
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Data collection: SMART (Bruker, 2000); cell 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).
Supporting information
10.1107/S1600536808011495/bt2701sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808011495/bt2701Isup2.hkl
To a stirring acetone solution (75 ml) of pivaloyl chloride (5.0 g, 0.04 mol) and ammonium thiocyanate (3.15 g, 0.04 mol), 1,2-diaminocyclohexane (2.37 g, 0.02 mol) in 40 ml of acetone was added dropwise. The solution mixture was refluxed for 1 h. The resulting solution was poured into a beaker containing some ice blocks. The white precipitate was filtered off and washed with distilled water and cold ethanol before dried under vacuum. Good quality crystals were obtained by recrystallization from DMSO.
After their location in the difference map, all H-atoms were fixed geometrically at ideal positions and allowed to ride on the parent C or N atoms with C—H = 0.93–0.97Å and N—H = 0.86Å with Uiso(H)= 1.2 (CH2 and NH) or 1.5Ueq(C)(CH3). The methyl groups were allowed to rotate but not to tip.
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).C18H32N4O2S2 | F(000) = 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 = 1.9–25.0° |
b = 19.065 (4) Å | µ = 0.27 mm−1 |
c = 10.378 (2) Å | T = 298 K |
β = 96.112 (4)° | 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) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.0°, θmin = 1.9° |
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 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0662P)2 + 0.3145P] where P = (Fo2 + 2Fc2)/3 |
3779 reflections | (Δ/σ)max = 0.001 |
241 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C18H32N4O2S2 | V = 2156.1 (8) Å3 |
Mr = 400.60 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.960 (2) Å | µ = 0.27 mm−1 |
b = 19.065 (4) Å | T = 298 K |
c = 10.378 (2) Å | 0.48 × 0.41 × 0.37 mm |
β = 96.112 (4)° |
Bruker SMART APEX CCD area-detector diffractometer | 3779 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2828 reflections with I > 2σ(I) |
Tmin = 0.883, Tmax = 0.908 | Rint = 0.026 |
10928 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.30 e Å−3 |
3779 reflections | Δρmin = −0.22 e Å−3 |
241 parameters |
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 |
Symmetry code: (i) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C18H32N4O2S2 |
Mr | 400.60 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 10.960 (2), 19.065 (4), 10.378 (2) |
β (°) | 96.112 (4) |
V (Å3) | 2156.1 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.48 × 0.41 × 0.37 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.883, 0.908 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10928, 3779, 2828 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.124, 1.07 |
No. of reflections | 3779 |
No. of parameters | 241 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.22 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
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) −x, −y, −z. |
Acknowledgements
The authors thank the Malaysian Government, Universiti Kebangsaan Malaysia, Universiti Malaysia Terengganu and the Ministry of Higher Education, Malaysia, for research grants OUP UKM OUP-BIT-28/20076 and UMT-FRGS-59001.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thiam, E. I., Diop, M., Gaye, M., Sall, A. S. & Barry, A. H. (2008). Acta Cryst. E64, o776. Web of Science CSD CrossRef IUCr Journals Google Scholar
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The title compound, (I), is a propionylthiourea derivatives and analogous to 1,2-bis(N'-benzoylthioureido)benzene, (Thiam et al., 2008), except that the benzene and benzoyl groups are replaced by cyclohexane and 2,2-dimethylpropionyl group respectively (Fig. 1). The bond lengths and angles are in normal ranges (Allen et al., 1987). The thiourea fragments [S1/N1/N2/C4 and S2/N3/N4/C11] are all planar, with a maximum deviation of 0.024 (2)Å from least-sqares plane for atom N2 and the dihedral angles between them is 78.55 (7)°.
There are two intramolecular hydrogen bonds, N2—H2···O1 and N3—H3···O2 (Table 1), forming two pseudo-six-membered rings (O1···H2—N2—C4—N1—C3—O1 and O2···H3—N3—C11—N4—C12—O2). In the crystal structure, the molecules are linked by intermolecular interactions, N—H···O and C—H···O forming centrosymmetric dimers (Fig. 2).