Literature DB >> 21200669

N-(Biphenyl-4-carbon-yl)-N'-(4-chloro-phen-yl)thio-urea.

Bohari M Yamin1, M Asyikin M Arif.   

Abstract

In the title compound, C(20)H(15)ClN(2)OS, the benzene rings of the biphenyl group are at an angle of 44.23 (12)°. The C(4)N(2)OS central thio-urea fragment makes dihedral angles with the benzene carbonyl and chloro-benzene rings of 55.96 (9) and 64.09 (9)°, respectively. The trans-cis geometry of the thio-urea group is stabilized by the intra-molecular hydrogen bond between the carbonyl O atom and the H atom of the cis-thio-amide. In the crystal structure, mol-ecules are linked by N-H⋯S and N-H⋯O inter-molecular hydrogen bonds to form one-dimensional chains along the c axis. C-H⋯π inter-actions also contribute to the stability of the mol-ecule.

Entities:  

Year:  2007        PMID： 21200669      PMCID： PMC2915178          DOI： 10.1107/S1600536807062265

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


Related literature

For related literature, see: Allen et al. (1987 ▶); Arif & Yamin (2007 ▶).

Experimental

Crystal data

C20H15ClN2OS M = 366.85 Monoclinic, a = 16.039 (7) Å b = 6.087 (3) Å c = 18.096 (8) Å β = 94.780 (8)° V = 1760.5 (14) Å3 Z = 4 Mo Kα radiation μ = 0.35 mm−1 T = 298 (2) K 0.49 × 0.46 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.848, T max = 0.966 9371 measured reflections 3475 independent reflections 2278 reflections with I > 2σ(I) R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.122 S = 1.02 3475 reflections 226 parameters H-atom parameters constrained Δρmax = 0.28 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, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062265/su2027sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062265/su2027Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H15ClN2OSF000 = 760
Mr = 366.85Dx = 1.384 Mg m−3
Monoclinic, P2/cMelting point: 164-166°C K
Hall symbol: -P 2ycMo Kα radiation λ = 0.71073 Å
a = 16.039 (7) ÅCell parameters from 1713 reflections
b = 6.087 (3) Åθ = 2.2–26.0º
c = 18.096 (8) ŵ = 0.35 mm−1
β = 94.780 (8)ºT = 298 (2) K
V = 1760.5 (14) Å3Block, colourless
Z = 40.49 × 0.46 × 0.10 mm
Bruker SMART APEX CCD area-detector diffractometer3475 independent reflections
Radiation source: fine-focus sealed tube2278 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
T = 298(2) Kθmax = 26.0º
ω scanθmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2000)h = −19→18
Tmin = 0.848, Tmax = 0.966k = −7→7
9371 measured reflectionsl = −22→12
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.122  w = 1/[σ2(Fo2) + (0.0596P)2 + 0.0946P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3475 reflectionsΔρmax = 0.28 e Å−3
226 parametersΔρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/Ueq
Cl11.37861 (5)0.39472 (17)0.18867 (5)0.1065 (4)
S11.08379 (4)0.38002 (11)0.42312 (3)0.0553 (2)
O10.95079 (10)0.9893 (3)0.32501 (9)0.0591 (5)
N10.97515 (11)0.7034 (3)0.40513 (10)0.0483 (5)
H10.95640.64400.44350.058*
N21.07779 (10)0.7027 (3)0.32382 (10)0.0487 (5)
H21.05370.81940.30570.058*
C10.79626 (14)0.7695 (4)0.42417 (12)0.0505 (6)
H1A0.80260.63330.40200.061*
C20.72746 (13)0.8084 (4)0.46287 (13)0.0504 (6)
H2A0.68720.69930.46560.060*
C30.71742 (13)1.0086 (4)0.49788 (12)0.0445 (6)
C40.64556 (14)1.0439 (4)0.54340 (13)0.0481 (6)
C50.62285 (15)0.8839 (4)0.59148 (14)0.0601 (7)
H50.65320.75380.59570.072*
C60.55587 (17)0.9127 (5)0.63367 (16)0.0752 (9)
H60.54160.80320.66610.090*
C70.51023 (17)1.1049 (6)0.62738 (16)0.0749 (9)
H70.46451.12460.65500.090*
C80.53267 (16)1.2669 (5)0.58009 (16)0.0759 (9)
H80.50261.39760.57630.091*
C90.59943 (15)1.2364 (5)0.53843 (15)0.0627 (7)
H90.61391.34680.50640.075*
C100.77729 (14)1.1700 (4)0.49070 (13)0.0525 (6)
H100.77131.30580.51320.063*
C110.84582 (14)1.1326 (4)0.45067 (13)0.0519 (6)
H110.88501.24320.44580.062*
C120.85579 (13)0.9293 (4)0.41789 (12)0.0431 (5)
C130.93135 (13)0.8825 (4)0.37742 (12)0.0451 (6)
C141.04533 (13)0.6039 (4)0.38029 (12)0.0425 (5)
C151.15067 (13)0.6247 (4)0.29167 (11)0.0426 (5)
C161.22033 (14)0.7565 (5)0.29525 (12)0.0572 (7)
H161.21990.89270.31850.069*
C171.29127 (15)0.6842 (5)0.26385 (15)0.0679 (8)
H171.33890.77190.26550.081*
C181.29059 (15)0.4827 (5)0.23047 (14)0.0605 (7)
C191.22169 (16)0.3514 (4)0.22703 (14)0.0594 (7)
H191.22260.21410.20460.071*
C201.15066 (15)0.4242 (4)0.25714 (13)0.0530 (6)
H201.10270.33760.25410.064*
U11U22U33U12U13U23
Cl10.0737 (5)0.1498 (9)0.1022 (7)0.0428 (5)0.0449 (5)0.0262 (6)
S10.0576 (4)0.0604 (4)0.0499 (4)0.0152 (3)0.0171 (3)0.0127 (3)
O10.0684 (11)0.0584 (11)0.0528 (10)0.0138 (9)0.0183 (8)0.0152 (9)
N10.0496 (11)0.0554 (13)0.0417 (11)0.0119 (10)0.0137 (9)0.0092 (9)
N20.0495 (11)0.0530 (12)0.0454 (11)0.0088 (9)0.0138 (9)0.0096 (10)
C10.0504 (14)0.0455 (15)0.0549 (15)0.0053 (12)0.0007 (11)−0.0092 (12)
C20.0434 (13)0.0483 (15)0.0594 (15)−0.0066 (11)0.0039 (11)−0.0050 (12)
C30.0415 (12)0.0462 (15)0.0456 (13)0.0027 (11)0.0029 (10)0.0012 (11)
C40.0419 (13)0.0507 (15)0.0519 (14)−0.0052 (11)0.0046 (10)−0.0057 (12)
C50.0554 (15)0.0614 (18)0.0644 (17)−0.0039 (13)0.0110 (13)0.0014 (14)
C60.0655 (18)0.090 (2)0.0726 (19)−0.0176 (17)0.0198 (15)0.0045 (17)
C70.0504 (16)0.100 (3)0.077 (2)−0.0100 (17)0.0222 (14)−0.0116 (19)
C80.0542 (17)0.084 (2)0.091 (2)0.0153 (15)0.0165 (15)−0.0057 (18)
C90.0575 (16)0.0625 (18)0.0699 (18)0.0081 (14)0.0166 (13)0.0053 (14)
C100.0577 (15)0.0411 (14)0.0606 (16)0.0008 (12)0.0165 (12)−0.0076 (12)
C110.0524 (14)0.0462 (15)0.0590 (15)−0.0046 (12)0.0157 (11)−0.0034 (12)
C120.0420 (12)0.0461 (14)0.0411 (13)0.0065 (11)0.0038 (10)0.0020 (11)
C130.0470 (13)0.0482 (15)0.0399 (13)0.0018 (11)0.0017 (10)−0.0025 (12)
C140.0403 (12)0.0489 (14)0.0390 (12)0.0017 (11)0.0066 (9)0.0001 (11)
C150.0441 (12)0.0497 (14)0.0347 (12)0.0004 (11)0.0077 (9)0.0060 (11)
C160.0613 (16)0.0607 (18)0.0505 (15)−0.0115 (13)0.0101 (12)−0.0079 (13)
C170.0453 (15)0.098 (2)0.0610 (17)−0.0151 (15)0.0092 (12)0.0054 (17)
C180.0505 (15)0.083 (2)0.0497 (15)0.0137 (15)0.0154 (12)0.0120 (15)
C190.0757 (18)0.0522 (16)0.0529 (15)0.0090 (14)0.0196 (13)0.0009 (13)
C200.0537 (15)0.0583 (17)0.0487 (14)−0.0076 (12)0.0138 (11)−0.0026 (13)
Cl1—C181.741 (2)C6—H60.9300
S1—C141.661 (2)C7—C81.374 (4)
O1—C131.212 (3)C7—H70.9300
N1—C131.369 (3)C8—C91.372 (3)
N1—C141.386 (3)C8—H80.9300
N1—H10.8600C9—H90.9300
N2—C141.329 (3)C10—C111.385 (3)
N2—C151.430 (3)C10—H100.9300
N2—H20.8600C11—C121.387 (3)
C1—C121.374 (3)C11—H110.9300
C1—C21.376 (3)C12—C131.495 (3)
C1—H1A0.9300C15—C201.371 (3)
C2—C31.389 (3)C15—C161.373 (3)
C2—H2A0.9300C16—C171.385 (3)
C3—C101.387 (3)C16—H160.9300
C3—C41.487 (3)C17—C181.367 (4)
C4—C51.375 (3)C17—H170.9300
C4—C91.385 (3)C18—C191.361 (4)
C5—C61.380 (3)C19—C201.376 (3)
C5—H50.9300C19—H190.9300
C6—C71.380 (4)C20—H200.9300
C13—N1—C14129.43 (18)C11—C10—C3121.2 (2)
C13—N1—H1115.3C11—C10—H10119.4
C14—N1—H1115.3C3—C10—H10119.4
C14—N2—C15123.29 (19)C10—C11—C12119.7 (2)
C14—N2—H2118.4C10—C11—H11120.2
C15—N2—H2118.4C12—C11—H11120.2
C12—C1—C2120.8 (2)C1—C12—C11119.4 (2)
C12—C1—H1A119.6C1—C12—C13120.2 (2)
C2—C1—H1A119.6C11—C12—C13120.4 (2)
C1—C2—C3120.8 (2)O1—C13—N1123.8 (2)
C1—C2—H2A119.6O1—C13—C12123.6 (2)
C3—C2—H2A119.6N1—C13—C12112.62 (19)
C10—C3—C2118.1 (2)N2—C14—N1115.62 (19)
C10—C3—C4121.6 (2)N2—C14—S1125.19 (16)
C2—C3—C4120.3 (2)N1—C14—S1119.17 (16)
C5—C4—C9118.2 (2)C20—C15—C16120.7 (2)
C5—C4—C3120.5 (2)C20—C15—N2120.8 (2)
C9—C4—C3121.4 (2)C16—C15—N2118.5 (2)
C4—C5—C6121.3 (3)C15—C16—C17119.2 (3)
C4—C5—H5119.3C15—C16—H16120.4
C6—C5—H5119.3C17—C16—H16120.4
C7—C6—C5119.6 (3)C18—C17—C16119.3 (2)
C7—C6—H6120.2C18—C17—H17120.3
C5—C6—H6120.2C16—C17—H17120.3
C8—C7—C6119.7 (3)C19—C18—C17121.6 (2)
C8—C7—H7120.1C19—C18—Cl1119.0 (2)
C6—C7—H7120.1C17—C18—Cl1119.4 (2)
C9—C8—C7120.1 (3)C18—C19—C20119.3 (3)
C9—C8—H8119.9C18—C19—H19120.4
C7—C8—H8119.9C20—C19—H19120.4
C8—C9—C4121.1 (3)C15—C20—C19119.9 (2)
C8—C9—H9119.5C15—C20—H20120.1
C4—C9—H9119.5C19—C20—H20120.1
C12—C1—C2—C3−1.4 (3)C14—N1—C13—O1−2.3 (4)
C1—C2—C3—C102.0 (3)C14—N1—C13—C12176.5 (2)
C1—C2—C3—C4−176.2 (2)C1—C12—C13—O1123.0 (3)
C10—C3—C4—C5−134.7 (3)C11—C12—C13—O1−58.3 (3)
C2—C3—C4—C543.4 (3)C1—C12—C13—N1−55.8 (3)
C10—C3—C4—C945.7 (3)C11—C12—C13—N1122.9 (2)
C2—C3—C4—C9−136.2 (2)C15—N2—C14—N1179.21 (19)
C9—C4—C5—C60.2 (4)C15—N2—C14—S11.0 (3)
C3—C4—C5—C6−179.4 (2)C13—N1—C14—N24.0 (3)
C4—C5—C6—C70.4 (4)C13—N1—C14—S1−177.63 (18)
C5—C6—C7—C8−1.0 (4)C14—N2—C15—C2063.7 (3)
C6—C7—C8—C91.0 (5)C14—N2—C15—C16−117.2 (3)
C7—C8—C9—C4−0.4 (4)C20—C15—C16—C17−0.4 (4)
C5—C4—C9—C8−0.2 (4)N2—C15—C16—C17−179.5 (2)
C3—C4—C9—C8179.4 (2)C15—C16—C17—C18−0.5 (4)
C2—C3—C10—C11−0.8 (4)C16—C17—C18—C190.3 (4)
C4—C3—C10—C11177.3 (2)C16—C17—C18—Cl1178.19 (19)
C3—C10—C11—C12−0.9 (4)C17—C18—C19—C200.7 (4)
C2—C1—C12—C11−0.4 (3)Cl1—C18—C19—C20−177.18 (19)
C2—C1—C12—C13178.3 (2)C16—C15—C20—C191.4 (4)
C10—C11—C12—C11.6 (3)N2—C15—C20—C19−179.5 (2)
C10—C11—C12—C13−177.2 (2)C18—C19—C20—C15−1.6 (4)
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.862.002.683 (3)135
N1—H1···S1i0.862.553.362 (3)157
N2—H2···O1ii0.862.583.210 (3)131
C1—H1A···Cg3ii0.932.983.586 (3)124
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2⋯O10.862.002.683 (3)135
N1—H1⋯S1i0.862.553.362 (3)157
N2—H2⋯O1ii0.862.583.210 (3)131
C1—H1A⋯Cg3ii0.932.983.586 (3)124

Symmetry codes: (i) ; (ii) . Cg3 is the centroid of atoms C15–C20.

  1 in total

1.  1-(Biphenyl-4-ylcarbon-yl)-3-(4-nitro-phen-yl)thio-urea.

Authors:  M Sukeri M Yusof; Sze Ting Wong; Bohari M Yamin
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-27
  1 in total

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