Literature DB >> 21577966

1-(1,3-Benzothia-zol-2-yl)-3-(4-chloro-benzo-yl)thio-urea.

M Sukeri M Yusof, Zakaria S Aishah, Wan M Khairul, Bohari M Yamin.

Abstract

The title compound, C(15)H(10)ClN(3)OS(2), adopts a cis-trans configuration across the thio-urea C-N bonds with respect to the positions of the benzothia-zole and 4-chloro-benzoyl groups relative to thiono S atom. An intra-molecular N-H⋯O hydrogen bond is present. In the crystal structure, mol-ecules are linked by a weak inter-molecular N-H⋯S hydrogen bond, forming centrosymmetric dimers.

Entities: Chemical Disease Gene

Year: 2009 PMID： 21577966 PMCID： PMC2970223 DOI： 10.1107/S160053680903743X

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the biological activity of thiadiazoles, see: Shukla & Srivastava (2008 ▶); Göblyös et al. (2005 ▶); Terzioglu & Gürsoy (2003 ▶); Rana et al. (2008 ▶). For their potential as insecticides and fungicides, see: Jian et al. (2005 ▶). For C—S and C—O bond lengths, see: Saeed & Flörke (2006 ▶); Yamin & Yusof (2003 ▶). For the structures of other benzoylthiourea derivatives, see: Dillen et al. (2006 ▶); Khawar Rauf et al. (2006 ▶); Weiqun et al. (2004 ▶).

Experimental

Crystal data

C15H10ClN3OS2 M = 347.83 Monoclinic, a = 11.726 (2) Å b = 17.934 (4) Å c = 7.2617 (16) Å β = 96.848 (4)° V = 1516.1 (6) Å3 Z = 4 Mo Kα radiation μ = 0.53 mm−1 T = 298 K 0.55 × 0.42 × 0.40 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.759, T max = 0.816 11030 measured reflections 3772 independent reflections 2891 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.109 S = 1.05 3772 reflections 199 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, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903743X/vm2003sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680903743X/vm2003Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₀ClN₃OS₂	F(000) = 712
M_r = 347.83	D_x = 1.524 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 906 reflections
a = 11.726 (2) Å	θ = 1.8–28.3°
b = 17.934 (4) Å	µ = 0.53 mm⁻¹
c = 7.2617 (16) Å	T = 298 K
β = 96.848 (4)°	Block, light yellow
V = 1516.1 (6) Å³	0.55 × 0.42 × 0.40 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3772 independent reflections
Radiation source: fine-focus sealed tube	2891 reflections with I > 2σ(I)
graphite	R_int = 0.022
Detector resolution: 83.66 pixels mm^-1	θ_max = 28.3°, θ_min = 1.8°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −23→20
T_min = 0.759, T_max = 0.816	l = −8→9
11030 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0606P)² + 0.1737P] where P = (F_o² + 2F_c²)/3
3772 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.22 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	U_iso*/U_eq
Cl1	0.84415 (5)	0.83795 (3)	0.39677 (9)	0.07175 (19)
S1	0.49665 (4)	0.38829 (3)	0.39437 (8)	0.05844 (16)
S2	0.58802 (4)	0.22891 (2)	0.41252 (6)	0.04563 (13)
O1	0.86117 (10)	0.46684 (7)	0.3645 (2)	0.0549 (3)
N3	0.80322 (12)	0.24282 (8)	0.3637 (2)	0.0474 (3)
N1	0.67029 (11)	0.48112 (8)	0.3894 (2)	0.0450 (3)
H1A	0.6183	0.5141	0.4005	0.054*
N2	0.71709 (11)	0.35696 (7)	0.3786 (2)	0.0434 (3)
H2A	0.7842	0.3750	0.3695	0.052*
C1	0.70106 (14)	0.63867 (10)	0.3181 (3)	0.0491 (4)
H1	0.6291	0.6194	0.2754	0.059*
C2	0.71738 (15)	0.71472 (10)	0.3236 (3)	0.0520 (4)
H2	0.6570	0.7469	0.2855	0.062*
C3	0.82429 (16)	0.74219 (10)	0.3862 (3)	0.0489 (4)
C4	0.91544 (15)	0.69616 (11)	0.4420 (3)	0.0551 (5)
H4	0.9873	0.7159	0.4832	0.066*
C5	0.89835 (14)	0.61965 (10)	0.4358 (3)	0.0507 (4)
H5	0.9594	0.5877	0.4722	0.061*
C6	0.79104 (13)	0.59043 (9)	0.3759 (2)	0.0418 (4)
C7	0.77928 (13)	0.50832 (10)	0.3753 (2)	0.0420 (4)
C8	0.63429 (13)	0.40769 (9)	0.3881 (2)	0.0417 (4)
C9	0.71104 (14)	0.27973 (9)	0.3813 (2)	0.0404 (4)
C10	0.78156 (15)	0.16707 (10)	0.3728 (2)	0.0459 (4)
C11	0.86167 (18)	0.11049 (11)	0.3579 (3)	0.0612 (5)
H11	0.9372	0.1220	0.3421	0.073*
C12	0.82695 (19)	0.03736 (12)	0.3672 (3)	0.0685 (6)
H12	0.8797	−0.0007	0.3568	0.082*
C13	0.7148 (2)	0.01951 (11)	0.3915 (3)	0.0657 (6)
H13	0.6932	−0.0303	0.3964	0.079*
C14	0.63489 (17)	0.07448 (10)	0.4087 (3)	0.0574 (5)
H14	0.5599	0.0624	0.4266	0.069*
C15	0.66891 (15)	0.14852 (9)	0.3988 (2)	0.0447 (4)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0907 (4)	0.0384 (3)	0.0882 (4)	−0.0049 (2)	0.0194 (3)	−0.0016 (2)
S1	0.0365 (2)	0.0450 (3)	0.0947 (4)	−0.00093 (18)	0.0117 (2)	−0.0050 (2)
S2	0.0387 (2)	0.0442 (2)	0.0534 (3)	−0.00318 (16)	0.00325 (18)	0.00143 (18)
O1	0.0381 (6)	0.0427 (7)	0.0842 (10)	0.0047 (5)	0.0088 (6)	−0.0007 (6)
N3	0.0428 (7)	0.0402 (8)	0.0602 (10)	−0.0005 (6)	0.0099 (7)	−0.0024 (6)
N1	0.0356 (7)	0.0381 (7)	0.0618 (9)	0.0029 (5)	0.0076 (6)	−0.0010 (6)
N2	0.0352 (6)	0.0381 (7)	0.0567 (9)	−0.0015 (5)	0.0045 (6)	−0.0020 (6)
C1	0.0366 (8)	0.0454 (9)	0.0649 (12)	0.0015 (7)	0.0046 (8)	0.0055 (8)
C2	0.0449 (9)	0.0453 (10)	0.0664 (12)	0.0083 (7)	0.0085 (8)	0.0083 (8)
C3	0.0570 (10)	0.0360 (8)	0.0557 (11)	−0.0018 (7)	0.0150 (8)	0.0002 (7)
C4	0.0428 (9)	0.0491 (10)	0.0727 (13)	−0.0069 (8)	0.0042 (8)	−0.0027 (9)
C5	0.0361 (8)	0.0456 (10)	0.0696 (12)	0.0023 (7)	0.0037 (8)	0.0028 (8)
C6	0.0355 (7)	0.0401 (9)	0.0503 (10)	0.0012 (6)	0.0071 (7)	0.0008 (7)
C7	0.0353 (7)	0.0438 (9)	0.0469 (9)	0.0007 (6)	0.0043 (7)	0.0009 (7)
C8	0.0391 (8)	0.0404 (8)	0.0455 (9)	0.0001 (6)	0.0043 (7)	−0.0014 (7)
C9	0.0387 (8)	0.0399 (8)	0.0419 (9)	−0.0021 (6)	0.0018 (6)	−0.0021 (6)
C10	0.0486 (9)	0.0411 (9)	0.0476 (10)	0.0009 (7)	0.0034 (7)	−0.0031 (7)
C11	0.0588 (11)	0.0462 (10)	0.0798 (14)	0.0061 (8)	0.0135 (10)	−0.0040 (9)
C12	0.0754 (14)	0.0442 (11)	0.0844 (16)	0.0115 (10)	0.0034 (12)	−0.0080 (10)
C13	0.0804 (15)	0.0391 (10)	0.0735 (14)	−0.0046 (10)	−0.0076 (11)	0.0004 (9)
C14	0.0605 (11)	0.0462 (10)	0.0628 (12)	−0.0098 (9)	−0.0035 (9)	0.0046 (8)
C15	0.0482 (9)	0.0414 (9)	0.0427 (9)	−0.0020 (7)	−0.0018 (7)	0.0006 (7)

Cl1—C3	1.7334 (19)	C2—H2	0.9300
S1—C8	1.6570 (17)	C3—C4	1.373 (3)
S2—C15	1.7352 (18)	C4—C5	1.386 (3)
S2—C9	1.7438 (17)	C4—H4	0.9300
O1—C7	1.2245 (19)	C5—C6	1.384 (2)
N3—C9	1.287 (2)	C5—H5	0.9300
N3—C10	1.385 (2)	C6—C7	1.479 (2)
N1—C8	1.383 (2)	C10—C15	1.397 (2)
N1—C7	1.383 (2)	C10—C11	1.396 (3)
N1—H1A	0.8600	C11—C12	1.377 (3)
N2—C8	1.338 (2)	C11—H11	0.9300
N2—C9	1.387 (2)	C12—C13	1.385 (3)
N2—H2A	0.8600	C12—H12	0.9300
C1—C2	1.377 (2)	C13—C14	1.376 (3)
C1—C6	1.390 (2)	C13—H13	0.9300
C1—H1	0.9300	C14—C15	1.391 (2)
C2—C3	1.373 (3)	C14—H14	0.9300

C15—S2—C9	87.73 (8)	O1—C7—C6	122.10 (15)
C9—N3—C10	109.80 (14)	N1—C7—C6	115.95 (14)
C8—N1—C7	128.28 (14)	N2—C8—N1	115.16 (14)
C8—N1—H1A	115.9	N2—C8—S1	125.01 (13)
C7—N1—H1A	115.9	N1—C8—S1	119.83 (12)
C8—N2—C9	129.75 (14)	N3—C9—N2	117.86 (15)
C8—N2—H2A	115.1	N3—C9—S2	117.51 (13)
C9—N2—H2A	115.1	N2—C9—S2	124.62 (12)
C2—C1—C6	120.65 (16)	N3—C10—C15	114.96 (15)
C2—C1—H1	119.7	N3—C10—C11	125.47 (17)
C6—C1—H1	119.7	C15—C10—C11	119.57 (17)
C3—C2—C1	118.89 (16)	C12—C11—C10	118.9 (2)
C3—C2—H2	120.6	C12—C11—H11	120.6
C1—C2—H2	120.6	C10—C11—H11	120.6
C4—C3—C2	122.00 (17)	C11—C12—C13	121.1 (2)
C4—C3—Cl1	119.14 (15)	C11—C12—H12	119.4
C2—C3—Cl1	118.86 (14)	C13—C12—H12	119.4
C3—C4—C5	118.75 (17)	C14—C13—C12	120.87 (19)
C3—C4—H4	120.6	C14—C13—H13	119.6
C5—C4—H4	120.6	C12—C13—H13	119.6
C6—C5—C4	120.48 (16)	C13—C14—C15	118.47 (19)
C6—C5—H5	119.8	C13—C14—H14	120.8
C4—C5—H5	119.8	C15—C14—H14	120.8
C5—C6—C1	119.21 (16)	C14—C15—C10	121.07 (17)
C5—C6—C7	117.30 (14)	C14—C15—S2	128.91 (15)
C1—C6—C7	123.48 (15)	C10—C15—S2	110.01 (13)
O1—C7—N1	121.94 (16)

C6—C1—C2—C3	0.3 (3)	C10—N3—C9—S2	0.4 (2)
C1—C2—C3—C4	0.5 (3)	C8—N2—C9—N3	177.61 (17)
C1—C2—C3—Cl1	−178.90 (15)	C8—N2—C9—S2	−4.0 (3)
C2—C3—C4—C5	−0.4 (3)	C15—S2—C9—N3	−0.44 (15)
Cl1—C3—C4—C5	179.00 (15)	C15—S2—C9—N2	−178.82 (15)
C3—C4—C5—C6	−0.5 (3)	C9—N3—C10—C15	−0.2 (2)
C4—C5—C6—C1	1.4 (3)	C9—N3—C10—C11	179.64 (19)
C4—C5—C6—C7	−179.30 (17)	N3—C10—C11—C12	−179.08 (18)
C2—C1—C6—C5	−1.3 (3)	C15—C10—C11—C12	0.8 (3)
C2—C1—C6—C7	179.44 (17)	C10—C11—C12—C13	−0.3 (3)
C8—N1—C7—O1	−2.2 (3)	C11—C12—C13—C14	−0.5 (3)
C8—N1—C7—C6	178.38 (16)	C12—C13—C14—C15	0.8 (3)
C5—C6—C7—O1	−24.7 (3)	C13—C14—C15—C10	−0.3 (3)
C1—C6—C7—O1	154.64 (18)	C13—C14—C15—S2	179.10 (15)
C5—C6—C7—N1	154.75 (16)	N3—C10—C15—C14	179.37 (16)
C1—C6—C7—N1	−25.9 (2)	C11—C10—C15—C14	−0.5 (3)
C9—N2—C8—N1	177.45 (16)	N3—C10—C15—S2	−0.1 (2)
C9—N2—C8—S1	−3.6 (3)	C11—C10—C15—S2	−179.97 (15)
C7—N1—C8—N2	2.7 (3)	C9—S2—C15—C14	−179.14 (18)
C7—N1—C8—S1	−176.34 (14)	C9—S2—C15—C10	0.28 (13)
C10—N3—C9—N2	178.94 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.88	2.6056 (19)	141
N1—H1A···S1ⁱ	0.86	2.75	3.5377 (17)	152
C5—H5···O1ⁱⁱ	0.93	2.49	3.389 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.88	2.6056 (19)	141
N1—H1A⋯S1ⁱ	0.86	2.75	3.5377 (17)	152

Symmetry code: (i) .

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