Literature DB >> 24454122

1-(4-Chlorophenyl)-3-(3-chloro-pro-pionyl)thio-urea.

Bohari M Yamin¹, Siti K C Soh¹, Siti Fairus M Yusoff¹.

Abstract

In the title compound, C10H10Cl2N2OS, the mol-ecule adopts a trans-cis conformation with respect to the position of the carbonyl group and the chloro-phenyl groups relative to the thiono group across the C-N bonds. The mol-ecule is stabilized by an N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by N-H⋯S and C-H⋯O hydrogen bonds, forming zigzag chains along the b-axis direction. C-H⋯π inter-actions are also present.

Entities: CellLine Chemical Disease Gene

Year: 2013 PMID： 24454122 PMCID： PMC3884346 DOI： 10.1107/S1600536813028511

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

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related thiourea derivatives, see: Othman et al. (2010 ▶); Yamin et al. (2011 ▶); Yamin & Othman (2011 ▶); Yusof et al. (2011 ▶).

Experimental

Crystal data

C10H10Cl2N2OS M = 277.16 Triclinic, a = 5.5151 (16) Å b = 9.045 (3) Å c = 12.387 (4) Å α = 101.000 (5)° β = 94.027 (5)° γ = 94.780 (5)° V = 602.1 (3) Å3 Z = 2 Mo Kα radiation μ = 0.69 mm−1 T = 298 K 0.47 × 0.21 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.737, T max = 0.947 5947 measured reflections 2227 independent reflections 1698 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.116 S = 1.22 2227 reflections 145 parameters H-atom parameters constrained Δρmax = 0.25 e Å−3 Δρmin = −0.29 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813028511/lr2115sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028511/lr2115Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813028511/lr2115Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₀H₁₀Cl₂N₂OS	V = 602.1 (3) Å³
M_r = 277.16	Z = 2
Triclinic, P1	F(000) = 284
Hall symbol: -P 1	D_x = 1.529 Mg m⁻³
a = 5.5151 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.045 (3) Å	µ = 0.69 mm⁻¹
c = 12.387 (4) Å	T = 298 K
α = 101.000 (5)°	Block, colourless
β = 94.027 (5)°	0.47 × 0.21 × 0.08 mm
γ = 94.780 (5)°

Bruker SMART APEX CCD area-detector diffractometer	2227 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.5°, θ_min = 1.7°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −10→10
T_min = 0.737, T_max = 0.947	l = −14→14
5947 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.22	w = 1/[σ²(F_o²) + (0.0289P)² + 0.4821P] where P = (F_o² + 2F_c²)/3
2227 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.1359 (2)	0.15827 (13)	0.11875 (8)	0.0690 (3)
Cl2	−0.63977 (19)	0.26746 (13)	0.95531 (9)	0.0666 (3)
S1	0.27725 (18)	0.51842 (10)	0.63440 (8)	0.0481 (3)
O1	−0.0306 (5)	0.1007 (3)	0.3804 (2)	0.0569 (7)
N1	0.2306 (5)	0.3097 (3)	0.4537 (2)	0.0405 (7)
H1A	0.3596	0.3612	0.4406	0.049*
N2	−0.0333 (5)	0.2657 (3)	0.5811 (2)	0.0422 (7)
H2A	−0.0743	0.1856	0.5312	0.051*
C1	0.1271 (7)	0.0805 (4)	0.1674 (3)	0.0491 (9)
H1B	0.0777	−0.0151	0.1878	0.059*
H1C	0.2346	0.0610	0.1087	0.059*
C2	0.2629 (7)	0.1865 (4)	0.2656 (3)	0.0465 (9)
H2B	0.4247	0.1547	0.2774	0.056*
H2C	0.2824	0.2874	0.2494	0.056*
C3	0.1378 (6)	0.1931 (4)	0.3701 (3)	0.0419 (8)
C4	0.1477 (6)	0.3573 (4)	0.5567 (3)	0.0369 (8)
C5	−0.1697 (6)	0.2764 (4)	0.6739 (3)	0.0382 (8)
C6	−0.1040 (7)	0.3699 (4)	0.7750 (3)	0.0503 (10)
H6A	0.0389	0.4351	0.7854	0.060*
C7	−0.2499 (7)	0.3672 (4)	0.8611 (3)	0.0522 (10)
H7A	−0.2060	0.4310	0.9291	0.063*
C8	−0.4593 (6)	0.2700 (4)	0.8458 (3)	0.0436 (9)
C9	−0.5279 (6)	0.1755 (4)	0.7458 (3)	0.0467 (9)
H9A	−0.6708	0.1104	0.7358	0.056*
C10	−0.3824 (6)	0.1788 (4)	0.6610 (3)	0.0442 (9)
H10A	−0.4269	0.1143	0.5932	0.053*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0701 (7)	0.0818 (8)	0.0521 (6)	0.0101 (6)	0.0018 (5)	0.0059 (5)
Cl2	0.0648 (7)	0.0843 (8)	0.0560 (6)	0.0065 (6)	0.0285 (5)	0.0192 (5)
S1	0.0518 (6)	0.0429 (5)	0.0431 (5)	−0.0112 (4)	0.0107 (4)	−0.0034 (4)
O1	0.0667 (18)	0.0535 (16)	0.0418 (14)	−0.0241 (14)	0.0165 (12)	−0.0041 (12)
N1	0.0400 (16)	0.0419 (16)	0.0347 (16)	−0.0095 (13)	0.0090 (12)	−0.0012 (12)
N2	0.0476 (17)	0.0416 (16)	0.0320 (15)	−0.0097 (13)	0.0099 (13)	−0.0027 (12)
C1	0.054 (2)	0.049 (2)	0.039 (2)	−0.0039 (18)	0.0112 (17)	−0.0030 (16)
C2	0.053 (2)	0.049 (2)	0.0352 (19)	−0.0072 (18)	0.0104 (17)	0.0039 (16)
C3	0.049 (2)	0.040 (2)	0.0351 (19)	−0.0011 (17)	0.0060 (16)	0.0035 (15)
C4	0.0367 (19)	0.0363 (19)	0.0359 (18)	−0.0024 (15)	0.0017 (14)	0.0057 (14)
C5	0.0395 (19)	0.043 (2)	0.0315 (18)	0.0014 (16)	0.0052 (14)	0.0053 (15)
C6	0.044 (2)	0.062 (2)	0.039 (2)	−0.0111 (18)	0.0075 (16)	0.0024 (18)
C7	0.057 (2)	0.063 (3)	0.033 (2)	−0.001 (2)	0.0095 (17)	0.0000 (17)
C8	0.041 (2)	0.052 (2)	0.042 (2)	0.0070 (17)	0.0135 (16)	0.0141 (17)
C9	0.040 (2)	0.048 (2)	0.052 (2)	−0.0045 (17)	0.0088 (17)	0.0114 (18)
C10	0.045 (2)	0.045 (2)	0.040 (2)	−0.0032 (17)	0.0050 (16)	0.0028 (16)

Cl1—C1	1.780 (4)	C2—C3	1.502 (4)
Cl2—C8	1.741 (3)	C2—H2B	0.9700
S1—C4	1.660 (3)	C2—H2C	0.9700
O1—C3	1.227 (4)	C5—C6	1.376 (5)
N1—C3	1.366 (4)	C5—C10	1.388 (5)
N1—C4	1.389 (4)	C6—C7	1.383 (5)
N1—H1A	0.8600	C6—H6A	0.9300
N2—C4	1.332 (4)	C7—C8	1.370 (5)
N2—C5	1.410 (4)	C7—H7A	0.9300
N2—H2A	0.8600	C8—C9	1.373 (5)
C1—C2	1.506 (4)	C9—C10	1.369 (5)
C1—H1B	0.9700	C9—H9A	0.9300
C1—H1C	0.9700	C10—H10A	0.9300

C3—N1—C4	129.6 (3)	N2—C4—N1	114.4 (3)
C3—N1—H1A	115.2	N2—C4—S1	127.3 (3)
C4—N1—H1A	115.2	N1—C4—S1	118.3 (2)
C4—N2—C5	131.6 (3)	C6—C5—C10	118.7 (3)
C4—N2—H2A	114.2	C6—C5—N2	125.5 (3)
C5—N2—H2A	114.2	C10—C5—N2	115.7 (3)
C2—C1—Cl1	111.2 (3)	C5—C6—C7	120.2 (3)
C2—C1—H1B	109.4	C5—C6—H6A	119.9
Cl1—C1—H1B	109.4	C7—C6—H6A	119.9
C2—C1—H1C	109.4	C8—C7—C6	119.7 (3)
Cl1—C1—H1C	109.4	C8—C7—H7A	120.1
H1B—C1—H1C	108.0	C6—C7—H7A	120.1
C3—C2—C1	113.6 (3)	C7—C8—C9	121.0 (3)
C3—C2—H2B	108.8	C7—C8—Cl2	119.1 (3)
C1—C2—H2B	108.8	C9—C8—Cl2	119.9 (3)
C3—C2—H2C	108.8	C10—C9—C8	118.9 (3)
C1—C2—H2C	108.8	C10—C9—H9A	120.6
H2B—C2—H2C	107.7	C8—C9—H9A	120.6
O1—C3—N1	122.7 (3)	C9—C10—C5	121.4 (3)
O1—C3—C2	123.2 (3)	C9—C10—H10A	119.3
N1—C3—C2	114.1 (3)	C5—C10—H10A	119.3

Cl1—C1—C2—C3	73.9 (4)	C10—C5—C6—C7	−0.8 (6)
C4—N1—C3—O1	−7.3 (6)	N2—C5—C6—C7	−178.1 (3)
C4—N1—C3—C2	173.8 (3)	C5—C6—C7—C8	0.5 (6)
C1—C2—C3—O1	13.7 (5)	C6—C7—C8—C9	−0.4 (6)
C1—C2—C3—N1	−167.4 (3)	C6—C7—C8—Cl2	179.7 (3)
C5—N2—C4—N1	−177.7 (3)	C7—C8—C9—C10	0.4 (6)
C5—N2—C4—S1	1.6 (6)	Cl2—C8—C9—C10	−179.6 (3)
C3—N1—C4—N2	7.8 (5)	C8—C9—C10—C5	−0.7 (6)
C3—N1—C4—S1	−171.5 (3)	C6—C5—C10—C9	0.9 (5)
C4—N2—C5—C6	−17.2 (6)	N2—C5—C10—C9	178.4 (3)
C4—N2—C5—C10	165.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.92	2.646 (4)	141
C6—H6A···S1	0.93	2.55	3.193 (4)	126
N1—H1A···S1ⁱ	0.86	2.52	3.367 (3)	169
C9—H9A···O1ⁱⁱ	0.93	2.55	3.402 (5)	152
C1—H1B···Cg1ⁱⁱⁱ	0.97	2.92	3.690 (4)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.92	2.646 (4)	141
N1—H1A⋯S1ⁱ	0.86	2.52	3.367 (3)	169
C9—H9A⋯O1ⁱⁱ	0.93	2.55	3.402 (5)	152
C1—H1B⋯Cg1ⁱⁱⁱ	0.97	2.92	3.690 (4)	137

Symmetry codes: (i) ; (ii) ; (iii) .

6 in total

1-(4-Chlorophenyl)-3-(3-chloro-pro-pionyl)thio-urea.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. N-(4-Chloro-butano-yl)-N'-phenyl-thio-urea.

3. N-(3-Chloro-propion-yl)-N'-phenyl-thio-urea.

4. N-(4-Bromo-butano-yl)-N'-phen-ylthio-urea.

5. N-(4-Chloro-butanoyl)-N'-(2-fluoro-phen-yl)thio-urea.

6. Structure validation in chemical crystallography.