1-[3-({[Bis(2-methyl­prop­yl)carbamo­thio­yl]amino}­carbon­yl)benzoyl]-3,3-bis­(2-methyl­prop­yl)thio­urea

Selvakumaran, N.; Karvembu, R.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813021053

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1368

doi:10.1107/S1600536813021053

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1-[3-({[Bis(2-methylpropyl)carbamothioyl]amino}carbonyl)benzoyl]-3,3-bis(2-methylpropyl)thiourea

N. Selvakumaran,^a R. Karvembu,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 28 July 2013; accepted 29 July 2013; online 3 August 2013)

The title compound, C₂₆H₄₂N₄O₂S₂, adopts a shallow U-shape as both pendant arms of the 1,3-substituted benzene ring are orientated in the same direction. The thione S atoms lie to the same side of the benzene ring and the carbonyl O atoms to the other. The most prominent feature of the crystal packing is the formation of inversion dimers mediated by N—H⋯S hydrogen bonds. One of the 2-methylpropyl groups is statistically disordered over two positions.

Related literature

For the use of the title compound in the synthesis of metal macrocycles, see: Nguyen et al. (2011 ). For the structure of the methanol solvate, see: Rodenstein et al. (2007 ).

Experimental

Crystal data

C₂₆H₄₂N₄O₂S₂
M_r = 506.76
Monoclinic, P 2₁ /c
a = 12.6926 (2) Å
b = 11.8015 (2) Å
c = 19.9701 (4) Å
β = 103.883 (2)°
V = 2903.97 (9) Å³
Z = 4
Cu Kα radiation
μ = 1.87 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ) T_min = 0.217, T_max = 1.000
11629 measured reflections
5743 independent reflections
5234 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.142
S = 1.01
5743 reflections
316 parameters
30 restraints
H-atom parameters constrained
Δρ_max = 0.89 e Å⁻³
Δρ_min = −0.82 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S2ⁱ	0.88	2.62	3.4745 (17)	163
N3—H3⋯S2ⁱ	0.88	2.54	3.3870 (18)	162
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536813021053/hg5336sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813021053/hg5336Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813021053/hg5336Isup3.cml

checkCIF report

Comment top

The title compound, (I), for which the structure of a methanol solvate is known (Rodenstein et al., 2007), plays a vital role in forming a metallamacrocyclic square-planar d⁸ metal complexes via self-assembly (Nguyen et al., 2011).

In (I), Fig. 1, there is an almost orthogonal relationship between adjacent thione and carbonyl groups as seen in the C10—N2—C9—S1 and C17—N3—C18—S2 torsion angles of -113.25 (18) and 112.56 (18)°, respectively. Globally, the molecule adopts a flattened U-shape. The thione-S atoms lie to one side of the plane through the central benzene and the carbonyl-O atoms to the other so that the molecule has approximate mirror symmetry. The structure reported here for (I) is quite distinct that that observed in the methanol solvate of (I) (Rodenstein et al., 2007). In the latter, the thione-S atoms lie to either side of the benzene ring and, to a first approximation, the carbonyl-O atoms are co-planar with the ring.

Being direct towards the centre of the U-shaped molecule, the nitrogen-bound hydrogen atoms are well placed to form two N—H···S hydrogen bonds with an inverted U-shaped molecule with the central pair forming an eight-membered {···HNCS}₂ synthon, Fig. 2 and Table 1. A detailed analysis of the crystal packing is precluded owing to the presence of disorder in the molecule.

Related literature top

For the use of the title compound in the synthesis of metal macrocycles, see: Nguyen et al. (2011). For the structure of the methanol solvate, see: Rodenstein et al. (2007).

Experimental top

Isophthaloyl dichloride (2.0302 g, 10 mmol) dissolved in acetone (80 ml) was placed in a dropping funnel and added drop wise with stirring to potassium thiocyanate (1.9436 g, 20 mmol) dissolved in acetone (80 ml), under an N₂ atmosphere, in a three-necked round bottom flask. The mixture was heated to reflux for 30 min. and then allowed to cool. A solution of diisobutylamine (2.2850 g, 20 mmol) in acetone (80 ml) was added drop wise from a dropping funnel to the reaction mixture and the resulting mixture was stirred for 2 h. Hydrochloric acid (0.1 N, 300 ml) was added and the resulting white solid was filtered off, washed with water and dried in vacuo. Single crystals were grown at room temperature from its acetonitrile solution. FT—IR (KBr): ν(N—H) 3275, ν(C═O) 1694, ν(C═C) 1604, ν(C═S) 1262 cm^-1.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 70% probability level.
	Fig. 2. A view of the supramolecular dimer sustained by N—H···S hydrogen bonding, shown as orange dashed lines.

1-[3-({[Bis(2-methylpropyl)carbamothioyl]amino}carbonyl)benzoyl]-3,3-bis(2-methylpropyl)thiourea top

Crystal data top

C₂₆H₄₂N₄O₂S₂	F(000) = 1096
M_r = 506.76	D_x = 1.159 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 7250 reflections
a = 12.6926 (2) Å	θ = 3.6–74.2°
b = 11.8015 (2) Å	µ = 1.87 mm⁻¹
c = 19.9701 (4) Å	T = 100 K
β = 103.883 (2)°	Prism, colourless
V = 2903.97 (9) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5743 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	5234 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.4°, θ_min = 3.6°
ω scan	h = −15→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −12→14
T_min = 0.217, T_max = 1.000	l = −24→24
11629 measured reflections

Refinement top

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0843P)² + 2.364P] where P = (F_o² + 2F_c²)/3
5743 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.89 e Å⁻³
30 restraints	Δρ_min = −0.82 e Å⁻³

Crystal data top

C₂₆H₄₂N₄O₂S₂	V = 2903.97 (9) Å³
M_r = 506.76	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.6926 (2) Å	µ = 1.87 mm⁻¹
b = 11.8015 (2) Å	T = 100 K
c = 19.9701 (4) Å	0.30 × 0.25 × 0.20 mm
β = 103.883 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5743 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	5234 reflections with I > 2σ(I)
T_min = 0.217, T_max = 1.000	R_int = 0.028
11629 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	30 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.01	Δρ_max = 0.89 e Å⁻³
5743 reflections	Δρ_min = −0.82 e Å⁻³
316 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.11609 (4)	0.55881 (4)	0.67655 (3)	0.02477 (15)
S2	0.62752 (4)	0.46118 (4)	0.44878 (3)	0.02293 (15)
O1	0.17340 (12)	0.22802 (13)	0.68690 (8)	0.0241 (3)
O2	0.61704 (11)	0.15808 (12)	0.54351 (7)	0.0206 (3)
N1	0.24077 (13)	0.43431 (13)	0.77683 (8)	0.0169 (3)
N2	0.25286 (13)	0.39332 (14)	0.66500 (8)	0.0170 (3)
H2	0.2964	0.4261	0.6426	0.020*
N3	0.56570 (13)	0.34366 (14)	0.54531 (9)	0.0176 (3)
H3	0.5191	0.3901	0.5572	0.021*
N4	0.75240 (13)	0.37320 (13)	0.56575 (9)	0.0178 (3)
C1	0.18861 (16)	0.48806 (17)	0.82699 (10)	0.0203 (4)
H1A	0.1745	0.5688	0.8145	0.024*
H1B	0.2388	0.4851	0.8733	0.024*
C2	0.08139 (17)	0.43044 (18)	0.82988 (11)	0.0219 (4)
H2A	0.0328	0.4316	0.7824	0.026*
C3	0.0975 (2)	0.3077 (2)	0.85294 (13)	0.0306 (5)
H3A	0.1339	0.2665	0.8223	0.046*
H3B	0.0268	0.2729	0.8511	0.046*
H3C	0.1421	0.3046	0.9003	0.046*
C4	0.02682 (19)	0.4997 (2)	0.87688 (13)	0.0323 (5)
H4A	−0.0413	0.4630	0.8796	0.048*
H4B	0.0116	0.5763	0.8580	0.048*
H4C	0.0752	0.5042	0.9231	0.048*
C5	0.33477 (16)	0.36086 (17)	0.80564 (10)	0.0196 (4)
H5A	0.3458	0.3086	0.7691	0.023*
H5B	0.3183	0.3143	0.8431	0.023*
C6	0.44031 (17)	0.42639 (19)	0.83420 (11)	0.0239 (4)
H6	0.4305	0.4746	0.8734	0.029*
C7	0.47084 (19)	0.5028 (2)	0.78033 (13)	0.0334 (5)
H7A	0.5390	0.5420	0.8008	0.050*
H7B	0.4132	0.5587	0.7643	0.050*
H7C	0.4800	0.4568	0.7412	0.050*
C8	0.52897 (19)	0.3391 (2)	0.86208 (13)	0.0347 (5)
H8A	0.5980	0.3782	0.8804	0.052*
H8B	0.5363	0.2881	0.8248	0.052*
H8C	0.5094	0.2952	0.8990	0.052*
C9	0.20600 (16)	0.45859 (16)	0.71007 (10)	0.0177 (4)
C10	0.23093 (15)	0.27912 (16)	0.65600 (10)	0.0173 (4)
C11	0.28645 (15)	0.22035 (16)	0.60795 (10)	0.0164 (4)
C12	0.23975 (16)	0.12179 (16)	0.57527 (10)	0.0183 (4)
H12	0.1725	0.0956	0.5824	0.022*
C13	0.29103 (16)	0.06192 (16)	0.53250 (10)	0.0196 (4)
H13	0.2580	−0.0040	0.5093	0.024*
C14	0.39096 (16)	0.09851 (16)	0.52349 (10)	0.0179 (4)
H14	0.4266	0.0568	0.4947	0.021*
C15	0.43890 (15)	0.19632 (16)	0.55670 (10)	0.0162 (4)
C16	0.38622 (15)	0.25765 (16)	0.59863 (9)	0.0158 (4)
H16	0.4182	0.3248	0.6208	0.019*
C17	0.54908 (15)	0.22891 (16)	0.54792 (10)	0.0164 (4)
C18	0.65585 (16)	0.38956 (16)	0.52398 (10)	0.0173 (4)
C19	0.85265 (15)	0.40405 (17)	0.54486 (11)	0.0200 (4)
H19A	0.8997	0.4496	0.5819	0.024*
H19B	0.8337	0.4515	0.5028	0.024*
C20	0.91545 (16)	0.29955 (17)	0.53062 (11)	0.0217 (4)
H20	0.9352	0.2529	0.5736	0.026*
C21	1.02006 (16)	0.33990 (19)	0.51283 (11)	0.0252 (4)
H21A	1.0612	0.3873	0.5504	0.038*
H21B	1.0020	0.3841	0.4700	0.038*
H21C	1.0639	0.2741	0.5067	0.038*
C22	0.84824 (19)	0.22679 (19)	0.47291 (13)	0.0292 (5)
H22A	0.7817	0.2023	0.4854	0.044*
H22B	0.8904	0.1601	0.4660	0.044*
H22C	0.8294	0.2711	0.4302	0.044*
C23	0.76747 (16)	0.33369 (17)	0.63803 (10)	0.0208 (4)
H23A	0.7282	0.2611	0.6375	0.025*	0.50
H23B	0.8456	0.3181	0.6570	0.025*	0.50
H23C	0.8314	0.2830	0.6501	0.025*	0.50
H23D	0.7030	0.2898	0.6423	0.025*	0.50
C24	0.7304 (4)	0.4126 (4)	0.6856 (2)	0.0249 (7)	0.50
H24	0.6498	0.4219	0.6718	0.030*	0.50
C25	0.7662 (18)	0.3648 (9)	0.7587 (4)	0.0535 (12)	0.50
H25A	0.7500	0.2835	0.7580	0.080*	0.50
H25B	0.7272	0.4038	0.7888	0.080*	0.50
H25C	0.8445	0.3764	0.7763	0.080*	0.50
C26	0.7866 (5)	0.5259 (4)	0.6858 (3)	0.0385 (8)	0.50
H26A	0.7744	0.5723	0.7239	0.058*	0.50
H26B	0.7571	0.5649	0.6420	0.058*	0.50
H26C	0.8647	0.5138	0.6916	0.058*	0.50
C24'	0.7841 (4)	0.4354 (4)	0.6890 (2)	0.0249 (7)	0.50
H24'	0.8598	0.4653	0.6964	0.030*	0.50
C25'	0.7669 (18)	0.3828 (10)	0.7565 (4)	0.0535 (12)	0.50
H25D	0.7828	0.4395	0.7934	0.080*	0.50
H25E	0.8156	0.3178	0.7695	0.080*	0.50
H25F	0.6915	0.3576	0.7494	0.080*	0.50
C26'	0.7058 (5)	0.5276 (4)	0.6693 (3)	0.0385 (8)	0.50
H26D	0.7060	0.5536	0.6227	0.058*	0.50
H26E	0.7257	0.5905	0.7019	0.058*	0.50
H26F	0.6331	0.5003	0.6700	0.058*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0289 (3)	0.0230 (3)	0.0233 (3)	0.00895 (19)	0.0080 (2)	0.00262 (19)
S2	0.0208 (3)	0.0234 (3)	0.0279 (3)	0.00407 (18)	0.0124 (2)	0.00993 (19)
O1	0.0282 (8)	0.0239 (7)	0.0252 (7)	−0.0074 (6)	0.0163 (6)	−0.0031 (6)
O2	0.0200 (7)	0.0164 (7)	0.0286 (8)	0.0007 (5)	0.0119 (6)	−0.0014 (5)
N1	0.0179 (8)	0.0179 (8)	0.0167 (8)	0.0007 (6)	0.0078 (6)	−0.0014 (6)
N2	0.0189 (8)	0.0175 (8)	0.0175 (8)	−0.0016 (6)	0.0101 (6)	−0.0002 (6)
N3	0.0165 (8)	0.0143 (8)	0.0255 (9)	0.0001 (6)	0.0121 (7)	0.0015 (6)
N4	0.0187 (8)	0.0141 (7)	0.0228 (8)	−0.0011 (6)	0.0092 (6)	0.0005 (6)
C1	0.0227 (10)	0.0206 (10)	0.0200 (9)	−0.0001 (8)	0.0098 (8)	−0.0042 (8)
C2	0.0219 (10)	0.0248 (10)	0.0217 (10)	−0.0019 (8)	0.0106 (8)	−0.0042 (8)
C3	0.0328 (12)	0.0269 (11)	0.0376 (13)	−0.0042 (9)	0.0190 (10)	0.0012 (9)
C4	0.0283 (11)	0.0371 (13)	0.0369 (13)	−0.0012 (10)	0.0186 (10)	−0.0105 (10)
C5	0.0212 (10)	0.0207 (10)	0.0180 (9)	0.0021 (8)	0.0071 (8)	0.0010 (7)
C6	0.0206 (10)	0.0299 (11)	0.0215 (10)	0.0002 (8)	0.0052 (8)	−0.0059 (8)
C7	0.0249 (11)	0.0387 (13)	0.0370 (13)	−0.0099 (10)	0.0085 (10)	−0.0008 (10)
C8	0.0256 (11)	0.0425 (14)	0.0326 (12)	0.0074 (10)	0.0002 (9)	−0.0060 (10)
C9	0.0188 (9)	0.0161 (9)	0.0202 (9)	−0.0026 (7)	0.0086 (8)	−0.0020 (7)
C10	0.0170 (9)	0.0193 (9)	0.0168 (9)	−0.0005 (7)	0.0063 (7)	0.0005 (7)
C11	0.0189 (9)	0.0156 (9)	0.0163 (9)	−0.0002 (7)	0.0070 (7)	0.0023 (7)
C12	0.0167 (9)	0.0177 (9)	0.0216 (9)	−0.0022 (7)	0.0065 (7)	0.0009 (7)
C13	0.0215 (10)	0.0157 (9)	0.0221 (10)	−0.0032 (7)	0.0058 (8)	−0.0023 (7)
C14	0.0202 (9)	0.0159 (9)	0.0187 (9)	0.0010 (7)	0.0071 (7)	−0.0012 (7)
C15	0.0175 (9)	0.0151 (9)	0.0171 (9)	−0.0002 (7)	0.0066 (7)	0.0029 (7)
C16	0.0182 (9)	0.0134 (8)	0.0164 (9)	−0.0017 (7)	0.0052 (7)	−0.0002 (7)
C17	0.0190 (9)	0.0157 (9)	0.0162 (9)	−0.0010 (7)	0.0078 (7)	−0.0005 (7)
C18	0.0192 (9)	0.0122 (8)	0.0235 (10)	0.0000 (7)	0.0110 (7)	−0.0003 (7)
C19	0.0160 (9)	0.0181 (9)	0.0285 (10)	−0.0021 (7)	0.0104 (8)	0.0025 (8)
C20	0.0220 (10)	0.0202 (10)	0.0261 (10)	0.0045 (8)	0.0118 (8)	0.0060 (8)
C21	0.0174 (10)	0.0325 (11)	0.0266 (11)	0.0029 (8)	0.0073 (8)	0.0022 (9)
C22	0.0303 (11)	0.0215 (10)	0.0416 (13)	−0.0044 (9)	0.0202 (10)	−0.0055 (9)
C23	0.0198 (9)	0.0217 (10)	0.0217 (10)	−0.0007 (8)	0.0067 (8)	0.0020 (8)
C24	0.026 (2)	0.0248 (17)	0.0264 (14)	−0.0041 (16)	0.0106 (18)	−0.0030 (13)
C25	0.072 (2)	0.066 (3)	0.0243 (14)	0.030 (3)	0.0160 (14)	0.0035 (15)
C26	0.050 (2)	0.0312 (17)	0.0356 (19)	0.0013 (19)	0.0119 (18)	−0.0110 (15)
C24'	0.026 (2)	0.0248 (17)	0.0264 (14)	−0.0041 (16)	0.0106 (18)	−0.0030 (13)
C25'	0.072 (2)	0.066 (3)	0.0243 (14)	0.030 (3)	0.0160 (14)	0.0035 (15)
C26'	0.050 (2)	0.0312 (17)	0.0356 (19)	0.0013 (19)	0.0119 (18)	−0.0110 (15)

Geometric parameters (Å, º) top

S1—C9	1.668 (2)	C12—H12	0.9500
S2—C18	1.685 (2)	C13—C14	1.392 (3)
O1—C10	1.222 (2)	C13—H13	0.9500
O2—C17	1.219 (2)	C14—C15	1.396 (3)
N1—C9	1.331 (3)	C14—H14	0.9500
N1—C1	1.470 (2)	C15—C16	1.393 (3)
N1—C5	1.475 (2)	C15—C17	1.501 (3)
N2—C10	1.379 (3)	C16—H16	0.9500
N2—C9	1.419 (2)	C19—C20	1.532 (3)
N2—H2	0.8800	C19—H19A	0.9900
N3—C17	1.374 (2)	C19—H19B	0.9900
N3—C18	1.421 (2)	C20—C22	1.524 (3)
N3—H3	0.8800	C20—C21	1.530 (3)
N4—C18	1.321 (3)	C20—H20	1.0000
N4—C19	1.477 (2)	C21—H21A	0.9800
N4—C23	1.485 (3)	C21—H21B	0.9800
C1—C2	1.535 (3)	C21—H21C	0.9800
C1—H1A	0.9900	C22—H22A	0.9800
C1—H1B	0.9900	C22—H22B	0.9800
C2—C3	1.519 (3)	C22—H22C	0.9800
C3—H3A	0.9800	C23—C24	1.485 (4)
C3—H3B	0.9800	C23—C24'	1.556 (4)
C3—H3C	0.9800	C23—H23A	0.9900
C2—C4	1.530 (3)	C23—H23B	0.9900
C2—H2A	1.0000	C23—H23C	0.9900
C4—H4A	0.9800	C23—H23D	0.9900
C4—H4B	0.9800	C24—C26	1.515 (6)
C4—H4C	0.9800	C24—C25	1.529 (8)
C5—C6	1.533 (3)	C24—H24	1.0000
C5—H5A	0.9900	C25—H25A	0.9800
C5—H5B	0.9900	C25—H25B	0.9800
C6—C7	1.523 (3)	C25—H25C	0.9800
C6—C8	1.528 (3)	C26—H26A	0.9800
C6—H6	1.0000	C26—H26B	0.9800
C7—H7A	0.9800	C26—H26C	0.9800
C7—H7B	0.9800	C24'—C26'	1.463 (6)
C7—H7C	0.9800	C24'—C25'	1.547 (8)
C8—H8A	0.9800	C24'—H24'	1.0000
C8—H8B	0.9800	C25'—H25D	0.9800
C8—H8C	0.9800	C25'—H25E	0.9800
C10—C11	1.491 (3)	C25'—H25F	0.9800
C11—C16	1.395 (3)	C26'—H26D	0.9800
C11—C12	1.395 (3)	C26'—H26E	0.9800
C12—C13	1.385 (3)	C26'—H26F	0.9800

C9—N1—C1	119.61 (16)	N3—C17—C15	114.39 (16)
C9—N1—C5	124.04 (16)	N4—C18—N3	116.55 (17)
C1—N1—C5	116.23 (15)	N4—C18—S2	127.12 (15)
C10—N2—C9	120.73 (16)	N3—C18—S2	116.32 (14)
C10—N2—H2	119.6	N4—C19—C20	112.09 (16)
C9—N2—H2	119.6	N4—C19—H19A	109.2
C17—N3—C18	121.97 (16)	C20—C19—H19A	109.2
C17—N3—H3	119.0	N4—C19—H19B	109.2
C18—N3—H3	119.0	C20—C19—H19B	109.2
C18—N4—C19	121.16 (17)	H19A—C19—H19B	107.9
C18—N4—C23	122.92 (16)	C22—C20—C21	111.05 (17)
C19—N4—C23	115.67 (16)	C22—C20—C19	111.87 (17)
N1—C1—C2	112.50 (16)	C21—C20—C19	108.17 (17)
N1—C1—H1A	109.1	C22—C20—H20	108.6
C2—C1—H1A	109.1	C21—C20—H20	108.6
N1—C1—H1B	109.1	C19—C20—H20	108.6
C2—C1—H1B	109.1	C20—C21—H21A	109.5
H1A—C1—H1B	107.8	C20—C21—H21B	109.5
C2—C3—H3A	109.5	H21A—C21—H21B	109.5
C2—C3—H3B	109.5	C20—C21—H21C	109.5
H3A—C3—H3B	109.5	H21A—C21—H21C	109.5
C2—C3—H3C	109.5	H21B—C21—H21C	109.5
H3A—C3—H3C	109.5	C20—C22—H22A	109.5
H3B—C3—H3C	109.5	C20—C22—H22B	109.5
C3—C2—C4	111.80 (19)	H22A—C22—H22B	109.5
C3—C2—C1	112.21 (18)	C20—C22—H22C	109.5
C4—C2—C1	108.81 (17)	H22A—C22—H22C	109.5
C3—C2—H2A	108.0	H22B—C22—H22C	109.5
C4—C2—H2A	108.0	C24—C23—N4	116.0 (2)
C1—C2—H2A	108.0	C24—C23—C24'	27.3 (2)
C2—C4—H4A	109.5	N4—C23—C24'	111.1 (2)
C2—C4—H4B	109.5	C24—C23—H23A	108.3
H4A—C4—H4B	109.5	N4—C23—H23A	108.3
C2—C4—H4C	109.5	C24'—C23—H23A	131.6
H4A—C4—H4C	109.5	C24—C23—H23B	108.3
H4B—C4—H4C	109.5	N4—C23—H23B	108.3
N1—C5—C6	113.66 (17)	C24'—C23—H23B	85.8
N1—C5—H5A	108.8	H23A—C23—H23B	107.4
C6—C5—H5A	108.8	C24—C23—H23C	126.2
N1—C5—H5B	108.8	N4—C23—H23C	109.4
C6—C5—H5B	108.8	C24'—C23—H23C	109.4
H5A—C5—H5B	107.7	H23A—C23—H23C	82.0
C7—C6—C8	111.48 (19)	H23B—C23—H23C	26.8
C7—C6—C5	112.55 (18)	C24—C23—H23D	82.9
C8—C6—C5	107.27 (18)	N4—C23—H23D	109.4
C7—C6—H6	108.5	C24'—C23—H23D	109.4
C8—C6—H6	108.5	H23A—C23—H23D	28.7
C5—C6—H6	108.5	H23B—C23—H23D	130.0
C6—C7—H7A	109.5	H23C—C23—H23D	108.0
C6—C7—H7B	109.5	C23—C24—C26	109.5 (3)
H7A—C7—H7B	109.5	C23—C24—C25	108.2 (6)
C6—C7—H7C	109.5	C26—C24—C25	106.9 (7)
H7A—C7—H7C	109.5	C23—C24—H24	110.7
H7B—C7—H7C	109.5	C26—C24—H24	110.7
C6—C8—H8A	109.5	C25—C24—H24	110.7
C6—C8—H8B	109.5	C24—C25—H25A	109.5
H8A—C8—H8B	109.5	C24—C25—H25B	109.5
C6—C8—H8C	109.5	H25A—C25—H25B	109.5
H8A—C8—H8C	109.5	C24—C25—H25C	109.5
H8B—C8—H8C	109.5	H25A—C25—H25C	109.5
N1—C9—N2	115.45 (17)	H25B—C25—H25C	109.5
N1—C9—S1	125.80 (15)	C24—C26—H26A	109.5
N2—C9—S1	118.74 (15)	C24—C26—H26B	109.5
O1—C10—N2	122.87 (18)	H26A—C26—H26B	109.5
O1—C10—C11	121.82 (18)	C24—C26—H26C	109.5
N2—C10—C11	115.26 (16)	H26A—C26—H26C	109.5
C16—C11—C12	119.89 (18)	H26B—C26—H26C	109.5
C16—C11—C10	121.58 (17)	C26'—C24'—C25'	107.7 (7)
C12—C11—C10	118.41 (17)	C26'—C24'—C23	114.8 (4)
C13—C12—C11	120.28 (18)	C25'—C24'—C23	103.6 (5)
C13—C12—H12	119.9	C26'—C24'—H24'	110.1
C11—C12—H12	119.9	C25'—C24'—H24'	110.1
C12—C13—C14	119.94 (18)	C23—C24'—H24'	110.1
C12—C13—H13	120.0	C24'—C25'—H25D	109.5
C14—C13—H13	120.0	C24'—C25'—H25E	109.5
C13—C14—C15	120.12 (18)	H25D—C25'—H25E	109.5
C13—C14—H14	119.9	C24'—C25'—H25F	109.5
C15—C14—H14	119.9	H25D—C25'—H25F	109.5
C16—C15—C14	119.86 (17)	H25E—C25'—H25F	109.5
C16—C15—C17	122.16 (17)	C24'—C26'—H26D	109.5
C14—C15—C17	117.94 (17)	C24'—C26'—H26E	109.5
C15—C16—C11	119.89 (17)	H26D—C26'—H26E	109.5
C15—C16—H16	120.1	C24'—C26'—H26F	109.5
C11—C16—H16	120.1	H26D—C26'—H26F	109.5
O2—C17—N3	123.74 (17)	H26E—C26'—H26F	109.5
O2—C17—C15	121.87 (17)

C9—N1—C1—C2	80.0 (2)	C10—C11—C16—C15	175.89 (17)
C5—N1—C1—C2	−103.8 (2)	C18—N3—C17—O2	12.4 (3)
N1—C1—C2—C3	62.2 (2)	C18—N3—C17—C15	−167.52 (17)
N1—C1—C2—C4	−173.59 (18)	C16—C15—C17—O2	142.2 (2)
C9—N1—C5—C6	96.8 (2)	C14—C15—C17—O2	−35.2 (3)
C1—N1—C5—C6	−79.3 (2)	C16—C15—C17—N3	−37.8 (3)
N1—C5—C6—C7	−57.2 (2)	C14—C15—C17—N3	144.76 (18)
N1—C5—C6—C8	179.81 (17)	C19—N4—C18—N3	172.06 (16)
C1—N1—C9—N2	−173.21 (16)	C23—N4—C18—N3	−13.9 (3)
C5—N1—C9—N2	10.8 (3)	C19—N4—C18—S2	−9.2 (3)
C1—N1—C9—S1	8.1 (3)	C23—N4—C18—S2	164.81 (15)
C5—N1—C9—S1	−167.84 (15)	C17—N3—C18—N4	−68.6 (2)
C10—N2—C9—N1	68.0 (2)	C17—N3—C18—S2	112.56 (18)
C10—N2—C9—S1	−113.25 (18)	C18—N4—C19—C20	−108.5 (2)
C9—N2—C10—O1	−1.9 (3)	C23—N4—C19—C20	77.1 (2)
C9—N2—C10—C11	−179.25 (17)	N4—C19—C20—C22	60.0 (2)
O1—C10—C11—C16	−148.7 (2)	N4—C19—C20—C21	−177.34 (17)
N2—C10—C11—C16	28.7 (3)	C18—N4—C23—C24	−65.4 (3)
O1—C10—C11—C12	27.3 (3)	C19—N4—C23—C24	108.9 (3)
N2—C10—C11—C12	−155.33 (18)	C18—N4—C23—C24'	−94.8 (3)
C16—C11—C12—C13	−1.2 (3)	C19—N4—C23—C24'	79.6 (3)
C10—C11—C12—C13	−177.27 (18)	N4—C23—C24—C26	−56.3 (4)
C11—C12—C13—C14	1.7 (3)	C24'—C23—C24—C26	29.6 (5)
C12—C13—C14—C15	−0.9 (3)	N4—C23—C24—C25	−172.5 (8)
C13—C14—C15—C16	−0.3 (3)	C24'—C23—C24—C25	−86.6 (10)
C13—C14—C15—C17	177.14 (18)	C24—C23—C24'—C26'	−58.2 (6)
C14—C15—C16—C11	0.8 (3)	N4—C23—C24'—C26'	47.9 (4)
C17—C15—C16—C11	−176.57 (17)	C24—C23—C24'—C25'	59.0 (10)
C12—C11—C16—C15	0.0 (3)	N4—C23—C24'—C25'	165.1 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S2ⁱ	0.88	2.62	3.4745 (17)	163
N3—H3···S2ⁱ	0.88	2.54	3.3870 (18)	162

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S2ⁱ	0.88	2.62	3.4745 (17)	163
N3—H3···S2ⁱ	0.88	2.54	3.3870 (18)	162

Symmetry code: (i) −x+1, −y+1, −z+1.

Footnotes

‡Additional correspondence author, e-mail: kar@nitt.edu.

Acknowledgements

NS thanks NITT for a Fellowship. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nguyen, H. H., Thang, P. C., Rodenstein, A., Kirmse, R. & Abram, U. (2011). Inorg. Chem. 50, 590–596. Web of Science CSD CrossRef CAS PubMed Google Scholar
Rodenstein, A., Richter, R. & Kirmse, R. (2007). Z. Anorg. Allg. Chem. 633, 1713–1717. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 9| September 2013| Page o1368

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[3-({[Bis(2-methyl­prop­yl)carbamo­thio­yl]amino}­carbon­yl)benzoyl]-3,3-bis­­(2-methyl­prop­yl)thio­urea

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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Acknowledgements

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organic compounds

1-[3-({[Bis(2-methylpropyl)carbamothioyl]amino}carbonyl)benzoyl]-3,3-bis(2-methylpropyl)thiourea