Literature DB >> 22904905

1-(3-Bromo-phen-yl)thio-urea.

Hoong-Kun Fun, Ching Kheng Quah, Prakash S Nayak, B Narayana, B K Sarojini.

Abstract

In the title compound, C(7)H(7)BrN(2)S, the thio-urea moiety is nearly planar (r.m.s. deviation = 0.004 Å) and it forms a dihedral angle of 66.72 (15)° with the benzene ring. The C-N-C-N2 torsion angle is 15.1 (4)°. In the crystal, mol-ecules are linked via N-H⋯S and N-H⋯N hydrogen bonds into sheets lying parallel to (101).

Entities: CellLine Chemical Disease Species

Year: 2012 PMID： 22904905 PMCID： PMC3414918 DOI： 10.1107/S1600536812031601

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

Related literature

For general background to and related structures of the title compound, see: Fun et al. (2012 ▶); Sarojini et al. (2007 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C7H7BrN2S M = 231.12 Triclinic, a = 5.5308 (8) Å b = 8.5316 (12) Å c = 9.4249 (14) Å α = 103.500 (3)° β = 90.878 (3)° γ = 97.232 (4)° V = 428.54 (11) Å3 Z = 2 Mo Kα radiation μ = 4.97 mm−1 T = 100 K 0.23 × 0.16 × 0.07 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.396, T max = 0.716 5292 measured reflections 1481 independent reflections 1354 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.024 wR(F 2) = 0.067 S = 1.09 1481 reflections 100 parameters H-atom parameters constrained Δρmax = 0.44 e Å−3 Δρmin = −0.48 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031601/hb6892sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031601/hb6892Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812031601/hb6892Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₇H₇BrN₂S	Z = 2
M_r = 231.12	F(000) = 228
Triclinic, P1	D_x = 1.791 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5308 (8) Å	Cell parameters from 3285 reflections
b = 8.5316 (12) Å	θ = 2.9–29.6°
c = 9.4249 (14) Å	µ = 4.97 mm⁻¹
α = 103.500 (3)°	T = 100 K
β = 90.878 (3)°	Plate, colourless
γ = 97.232 (4)°	0.23 × 0.16 × 0.07 mm
V = 428.54 (11) Å³

Bruker SMART APEXII DUO CCD diffractometer	1481 independent reflections
Radiation source: fine-focus sealed tube	1354 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
T_min = 0.396, T_max = 0.716	k = −10→10
5292 measured reflections	l = −11→11

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0373P)² + 0.1495P] where P = (F_o² + 2F_c²)/3
1481 reflections	(Δ/σ)_max = 0.001
100 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Br1	0.80456 (5)	0.08100 (4)	0.30695 (3)	0.02513 (13)
S1	0.39118 (12)	0.25378 (9)	1.02969 (8)	0.01925 (18)
N1	0.7109 (4)	0.3643 (3)	0.8568 (3)	0.0188 (5)
H1N1	0.6478	0.4767	0.8945	0.023*
N2	0.7347 (4)	0.1050 (3)	0.8821 (3)	0.0201 (5)
H1N2	0.6763	0.0004	0.8990	0.024*
H2N2	0.8746	0.1112	0.8318	0.024*
C1	1.0878 (5)	0.4459 (4)	0.7452 (3)	0.0208 (6)
H1A	1.1426	0.5220	0.8340	0.025*
C2	1.2308 (5)	0.4300 (4)	0.6236 (3)	0.0241 (7)
H2A	1.3836	0.4966	0.6297	0.029*
C3	1.1532 (5)	0.3180 (4)	0.4929 (3)	0.0220 (6)
H3A	1.2529	0.3057	0.4108	0.026*
C4	0.9281 (5)	0.2254 (4)	0.4859 (3)	0.0185 (6)
C5	0.7812 (5)	0.2390 (3)	0.6044 (3)	0.0174 (6)
H5A	0.6265	0.1744	0.5972	0.021*
C6	0.8650 (5)	0.3495 (4)	0.7348 (3)	0.0183 (6)
C7	0.6287 (5)	0.2392 (3)	0.9158 (3)	0.0164 (6)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02112 (19)	0.0317 (2)	0.01968 (19)	0.00583 (13)	−0.00184 (11)	−0.00064 (13)
S1	0.0192 (4)	0.0159 (4)	0.0237 (4)	0.0044 (3)	0.0047 (3)	0.0055 (3)
N1	0.0211 (12)	0.0164 (13)	0.0189 (13)	0.0044 (10)	0.0024 (10)	0.0029 (10)
N2	0.0210 (12)	0.0149 (13)	0.0256 (13)	0.0053 (10)	0.0052 (10)	0.0057 (10)
C1	0.0207 (15)	0.0199 (16)	0.0220 (15)	0.0030 (12)	−0.0053 (12)	0.0055 (12)
C2	0.0155 (15)	0.0282 (18)	0.0283 (17)	−0.0024 (13)	−0.0029 (13)	0.0092 (14)
C3	0.0163 (15)	0.0281 (17)	0.0224 (15)	0.0058 (13)	0.0008 (12)	0.0061 (13)
C4	0.0181 (14)	0.0192 (16)	0.0185 (14)	0.0064 (12)	−0.0030 (11)	0.0036 (12)
C5	0.0161 (14)	0.0140 (15)	0.0230 (15)	0.0033 (11)	−0.0007 (11)	0.0052 (11)
C6	0.0194 (14)	0.0198 (15)	0.0179 (15)	0.0065 (12)	0.0011 (11)	0.0069 (12)
C7	0.0169 (14)	0.0135 (14)	0.0176 (14)	0.0007 (11)	−0.0044 (11)	0.0025 (11)

Br1—C4	1.900 (3)	C1—C2	1.393 (4)
S1—C7	1.707 (3)	C1—H1A	0.9500
N1—C7	1.348 (4)	C2—C3	1.395 (4)
N1—C6	1.433 (4)	C2—H2A	0.9500
N1—H1N1	1.0468	C3—C4	1.380 (4)
N2—C7	1.327 (4)	C3—H3A	0.9500
N2—H1N2	0.9608	C4—C5	1.383 (4)
N2—H2N2	0.9156	C5—C6	1.395 (4)
C1—C6	1.381 (4)	C5—H5A	0.9500

C7—N1—C6	123.6 (2)	C2—C3—H3A	120.9
C7—N1—H1N1	119.2	C3—C4—C5	122.0 (3)
C6—N1—H1N1	116.9	C3—C4—Br1	120.0 (2)
C7—N2—H1N2	127.4	C5—C4—Br1	117.9 (2)
C7—N2—H2N2	116.3	C4—C5—C6	118.6 (3)
H1N2—N2—H2N2	116.2	C4—C5—H5A	120.7
C6—C1—C2	119.0 (3)	C6—C5—H5A	120.7
C6—C1—H1A	120.5	C1—C6—C5	121.0 (3)
C2—C1—H1A	120.5	C1—C6—N1	120.6 (3)
C1—C2—C3	121.1 (3)	C5—C6—N1	118.3 (3)
C1—C2—H2A	119.5	N2—C7—N1	118.5 (3)
C3—C2—H2A	119.5	N2—C7—S1	121.2 (2)
C4—C3—C2	118.3 (3)	N1—C7—S1	120.3 (2)
C4—C3—H3A	120.9

C6—C1—C2—C3	−0.5 (4)	C2—C1—C6—N1	−178.9 (2)
C1—C2—C3—C4	1.4 (4)	C4—C5—C6—C1	1.3 (4)
C2—C3—C4—C5	−1.0 (4)	C4—C5—C6—N1	179.3 (2)
C2—C3—C4—Br1	176.0 (2)	C7—N1—C6—C1	−123.6 (3)
C3—C4—C5—C6	−0.3 (4)	C7—N1—C6—C5	58.4 (4)
Br1—C4—C5—C6	−177.34 (19)	C6—N1—C7—N2	15.1 (4)
C2—C1—C6—C5	−0.9 (4)	C6—N1—C7—S1	−164.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···S1ⁱ	1.05	2.28	3.307 (3)	166
N2—H1N2···S1ⁱⁱ	0.96	2.40	3.349 (3)	168
N2—H2N2···Br1ⁱⁱⁱ	0.92	2.71	3.468 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯S1ⁱ	1.05	2.28	3.307 (3)	166
N2—H1N2⋯S1ⁱⁱ	0.96	2.40	3.349 (3)	168
N2—H2N2⋯Br1ⁱⁱⁱ	0.92	2.71	3.468 (2)	141

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

3 in total

1 in total

1. 1-(2,4-Difluoro-phen-yl)thio-urea.

Authors: Hoong-Kun Fun; Ching Kheng Quah; Prakash S Nayak; B Narayana; B K Sarojini
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-07-18