Literature DB >> 22059038

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

M Sukeri M Yusof, Sze Ting Wong, Bohari M Yamin.   

Abstract

In the title compound, C(20)H(15)N(3)O(3)S, the two benzene rings of the biphenyl group form a dihedral angle of 40.11 (15)°. The conformation of the mol-ecule is trans-cis and is stabilized by two intra-molecular N-H⋯O and C-H⋯S hydrogen bonds. In the crystal structure, the mol-ecules are linked by weak π-π stacking inter-actions [centroid-centroid distance = 3.991 (2) Å].

Entities:  

Year:  2011        PMID： 22059038      PMCID： PMC3200649          DOI： 10.1107/S160053681103426X

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


Related literature

For related structures, see: Arif &Yamin (2007 ▶); Yamin & Arif (2008 ▶). For standard bond lengths, see: Allen et al. (2003 ▶).

Experimental

Crystal data

C20H15N3O3S M = 377.41 Monoclinic, a = 12.154 (2) Å b = 9.4509 (18) Å c = 17.471 (3) Å β = 118.133 (9)° V = 1769.7 (5) Å3 Z = 4 Mo Kα radiation μ = 0.21 mm−1 T = 298 K 0.38 × 0.14 × 0.07 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.925, T max = 0.986 9891 measured reflections 3116 independent reflections 2268 reflections with I > 2/s(I) R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.060 wR(F 2) = 0.143 S = 0.88 3116 reflections 244 parameters H-atom parameters constrained Δρmax = 0.26 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: OLEX2 (Dolomanov et al., 2009 ▶), SHELXTL (Sheldrick, 2008 ▶), PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103426X/bx2367sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103426X/bx2367Isup2.hkl Supplementary material file. DOI: 10.1107/S160053681103426X/bx2367Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H15N3O3SF(000) = 784
Mr = 377.41Dx = 1.416 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 777 reflections
a = 12.154 (2) Åθ = 1.9–25.0°
b = 9.4509 (18) ŵ = 0.21 mm−1
c = 17.471 (3) ÅT = 298 K
β = 118.133 (9)°Slab, light yellow
V = 1769.7 (5) Å30.38 × 0.14 × 0.07 mm
Z = 4
Bruker SMART APEX CCD area-detector diffractometer3116 independent reflections
Radiation source: fine-focus sealed tube2268 reflections with I > 2/s(I)
graphiteRint = 0.043
Detector resolution: 83.66 pixels mm-1θmax = 25.0°, θmin = 1.9°
ω scanh = −13→14
Absorption correction: multi-scan (SADABS; Bruker, 2000)k = −10→11
Tmin = 0.925, Tmax = 0.986l = −20→20
9891 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 0.88w = 1/[σ2(Fo2) + (0.0447P)2 + 3.2573P] where P = (Fo2 + 2Fc2)/3
3116 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −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.
xyzUiso*/Ueq
S10.34844 (10)−0.26185 (12)−0.10149 (6)0.0687 (4)
O10.3207 (2)−0.5537 (3)0.09461 (16)0.0618 (7)
O21.0052 (2)−0.1773 (3)0.30122 (17)0.0662 (7)
O30.9535 (3)−0.0226 (3)0.19967 (19)0.0773 (9)
N10.2547 (2)−0.4403 (3)−0.03407 (17)0.0445 (7)
H10.1906−0.4296−0.08420.053*
N20.4557 (2)−0.3739 (3)0.05899 (17)0.0473 (7)
H2A0.4451−0.43530.09130.057*
N30.9295 (3)−0.1246 (3)0.2325 (2)0.0540 (8)
C1−0.3311 (3)−0.7919 (4)−0.1811 (2)0.0524 (9)
H1A−0.3269−0.7079−0.20740.063*
C2−0.4442 (3)−0.8619 (5)−0.2122 (2)0.0612 (10)
H2B−0.5157−0.8240−0.25780.073*
C3−0.4498 (4)−0.9871 (5)−0.1752 (3)0.0674 (12)
H3A−0.5255−1.0347−0.19620.081*
C4−0.3461 (4)−1.0434 (5)−0.1080 (3)0.0717 (12)
H4−0.3508−1.1292−0.08370.086*
C5−0.2324 (4)−0.9710 (4)−0.0758 (2)0.0595 (10)
H5−0.1617−1.0090−0.02950.071*
C6−0.2238 (3)−0.8443 (3)−0.1117 (2)0.0423 (8)
C7−0.1055 (3)−0.7659 (3)−0.0786 (2)0.0402 (7)
C8−0.0235 (3)−0.7554 (4)0.0100 (2)0.0468 (8)
H8−0.0436−0.79950.04930.056*
C90.0873 (3)−0.6809 (4)0.0405 (2)0.0462 (8)
H90.1410−0.67630.09990.055*
C100.1184 (3)−0.6134 (3)−0.0165 (2)0.0398 (7)
C110.0382 (3)−0.6242 (3)−0.1049 (2)0.0435 (8)
H110.0586−0.5800−0.14400.052*
C12−0.0709 (3)−0.6991 (4)−0.1351 (2)0.0471 (8)
H12−0.1229−0.7055−0.19460.056*
C130.2392 (3)−0.5352 (3)0.0202 (2)0.0450 (8)
C140.3579 (3)−0.3590 (3)−0.0200 (2)0.0433 (8)
C150.5734 (3)−0.3067 (3)0.0989 (2)0.0407 (8)
C160.6628 (3)−0.3681 (4)0.1744 (2)0.0458 (8)
H160.6438−0.44990.19540.055*
C170.7800 (3)−0.3090 (4)0.2191 (2)0.0484 (8)
H170.8405−0.35040.26980.058*
C180.8055 (3)−0.1871 (4)0.1869 (2)0.0452 (8)
C190.7179 (3)−0.1240 (4)0.1130 (2)0.0557 (9)
H190.7372−0.04180.09260.067*
C200.5997 (3)−0.1833 (4)0.0686 (2)0.0561 (9)
H200.5387−0.14010.01880.067*
U11U22U33U12U13U23
S10.0687 (7)0.0718 (7)0.0517 (6)−0.0203 (6)0.0169 (5)0.0114 (5)
O10.0406 (14)0.0756 (18)0.0498 (15)−0.0105 (12)0.0054 (12)0.0164 (13)
O20.0439 (15)0.0724 (18)0.0605 (17)−0.0035 (13)0.0068 (13)−0.0029 (14)
O30.0691 (19)0.075 (2)0.0768 (19)−0.0285 (16)0.0255 (16)0.0006 (16)
N10.0330 (15)0.0523 (17)0.0412 (15)−0.0026 (13)0.0118 (13)0.0020 (13)
N20.0439 (17)0.0477 (16)0.0481 (16)−0.0050 (13)0.0198 (14)0.0046 (13)
N30.0472 (19)0.056 (2)0.0563 (19)−0.0065 (15)0.0223 (17)−0.0103 (16)
C10.045 (2)0.055 (2)0.050 (2)−0.0013 (17)0.0155 (18)−0.0062 (17)
C20.039 (2)0.075 (3)0.060 (2)−0.0044 (19)0.0147 (18)−0.022 (2)
C30.050 (2)0.082 (3)0.076 (3)−0.028 (2)0.034 (2)−0.032 (2)
C40.082 (3)0.066 (3)0.075 (3)−0.026 (2)0.043 (3)−0.006 (2)
C50.055 (2)0.058 (2)0.058 (2)−0.0060 (19)0.0209 (19)0.0014 (19)
C60.0398 (19)0.0454 (19)0.0434 (18)−0.0018 (15)0.0211 (16)−0.0078 (15)
C70.0355 (18)0.0381 (18)0.0447 (18)0.0028 (14)0.0171 (15)−0.0019 (14)
C80.0411 (19)0.055 (2)0.0437 (19)−0.0005 (16)0.0192 (16)0.0033 (16)
C90.0369 (18)0.060 (2)0.0349 (17)−0.0019 (16)0.0112 (15)0.0011 (16)
C100.0333 (17)0.0415 (18)0.0416 (18)0.0054 (14)0.0152 (15)0.0004 (14)
C110.0423 (19)0.049 (2)0.0438 (19)0.0019 (16)0.0239 (16)0.0039 (15)
C120.0409 (19)0.056 (2)0.0356 (17)−0.0030 (16)0.0112 (15)−0.0014 (15)
C130.0371 (19)0.0444 (19)0.047 (2)0.0019 (15)0.0151 (17)0.0007 (16)
C140.0384 (19)0.0388 (18)0.0474 (19)0.0024 (15)0.0160 (16)−0.0037 (15)
C150.0370 (18)0.0422 (18)0.0447 (18)−0.0019 (15)0.0206 (16)−0.0044 (15)
C160.042 (2)0.047 (2)0.050 (2)−0.0038 (16)0.0229 (17)0.0040 (16)
C170.043 (2)0.055 (2)0.0412 (19)0.0029 (17)0.0151 (16)0.0006 (16)
C180.0373 (18)0.0473 (19)0.049 (2)−0.0056 (16)0.0185 (16)−0.0078 (16)
C190.054 (2)0.046 (2)0.061 (2)−0.0100 (18)0.022 (2)0.0050 (18)
C200.046 (2)0.054 (2)0.057 (2)−0.0009 (18)0.0153 (18)0.0103 (18)
S1—C141.652 (3)C6—C71.472 (4)
O1—C131.219 (4)C7—C121.393 (4)
O2—N31.222 (4)C7—C81.394 (4)
O3—N31.226 (4)C8—C91.384 (4)
N1—C131.382 (4)C8—H80.9300
N1—C141.391 (4)C9—C101.378 (4)
N1—H10.8605C9—H90.9300
N2—C141.338 (4)C10—C111.387 (4)
N2—C151.413 (4)C10—C131.492 (4)
N2—H2A0.8601C11—C121.370 (4)
N3—C181.457 (4)C11—H110.9300
C1—C21.385 (5)C12—H120.9300
C1—C61.388 (4)C15—C201.379 (5)
C1—H1A0.9300C15—C161.381 (4)
C2—C31.365 (6)C16—C171.379 (4)
C2—H2B0.9300C16—H160.9300
C3—C41.361 (6)C17—C181.380 (5)
C3—H3A0.9300C17—H170.9300
C4—C51.400 (5)C18—C191.363 (5)
C4—H40.9300C19—C201.389 (5)
C5—C61.378 (5)C19—H190.9300
C5—H50.9300C20—H200.9300
C13—N1—C14129.9 (3)C8—C9—H9119.8
C13—N1—H1115.1C9—C10—C11118.8 (3)
C14—N1—H1115.1C9—C10—C13117.9 (3)
C14—N2—C15131.5 (3)C11—C10—C13123.3 (3)
C14—N2—H2A114.3C12—C11—C10120.7 (3)
C15—N2—H2A114.2C12—C11—H11119.6
O2—N3—O3123.1 (3)C10—C11—H11119.6
O2—N3—C18118.5 (3)C11—C12—C7121.5 (3)
O3—N3—C18118.4 (3)C11—C12—H12119.3
C2—C1—C6121.5 (4)C7—C12—H12119.3
C2—C1—H1A119.3O1—C13—N1121.3 (3)
C6—C1—H1A119.3O1—C13—C10121.9 (3)
C3—C2—C1119.4 (4)N1—C13—C10116.8 (3)
C3—C2—H2B120.3N2—C14—N1114.4 (3)
C1—C2—H2B120.3N2—C14—S1127.9 (3)
C4—C3—C2120.9 (4)N1—C14—S1117.7 (2)
C4—C3—H3A119.5C20—C15—C16120.2 (3)
C2—C3—H3A119.5C20—C15—N2123.7 (3)
C3—C4—C5119.5 (4)C16—C15—N2116.1 (3)
C3—C4—H4120.2C17—C16—C15120.5 (3)
C5—C4—H4120.2C17—C16—H16119.7
C6—C5—C4120.9 (4)C15—C16—H16119.7
C6—C5—H5119.5C16—C17—C18118.5 (3)
C4—C5—H5119.5C16—C17—H17120.7
C5—C6—C1117.8 (3)C18—C17—H17120.7
C5—C6—C7121.9 (3)C19—C18—C17121.7 (3)
C1—C6—C7120.3 (3)C19—C18—N3119.0 (3)
C12—C7—C8117.2 (3)C17—C18—N3119.2 (3)
C12—C7—C6121.0 (3)C18—C19—C20119.6 (3)
C8—C7—C6121.7 (3)C18—C19—H19120.2
C9—C8—C7121.3 (3)C20—C19—H19120.2
C9—C8—H8119.3C15—C20—C19119.5 (3)
C7—C8—H8119.3C15—C20—H20120.3
C10—C9—C8120.4 (3)C19—C20—H20120.3
C10—C9—H9119.8
C6—C1—C2—C3−1.8 (5)C9—C10—C13—O115.8 (5)
C1—C2—C3—C40.5 (6)C11—C10—C13—O1−162.5 (3)
C2—C3—C4—C50.7 (6)C9—C10—C13—N1−164.2 (3)
C3—C4—C5—C6−0.6 (6)C11—C10—C13—N117.4 (5)
C4—C5—C6—C1−0.6 (5)C15—N2—C14—N1−177.0 (3)
C4—C5—C6—C7179.7 (3)C15—N2—C14—S15.4 (5)
C2—C1—C6—C51.8 (5)C13—N1—C14—N2−1.4 (5)
C2—C1—C6—C7−178.5 (3)C13—N1—C14—S1176.4 (3)
C5—C6—C7—C12139.9 (3)C14—N2—C15—C2016.4 (5)
C1—C6—C7—C12−39.8 (5)C14—N2—C15—C16−166.6 (3)
C5—C6—C7—C8−40.0 (5)C20—C15—C16—C17−1.7 (5)
C1—C6—C7—C8140.3 (3)N2—C15—C16—C17−178.8 (3)
C12—C7—C8—C90.5 (5)C15—C16—C17—C180.4 (5)
C6—C7—C8—C9−179.7 (3)C16—C17—C18—C190.5 (5)
C7—C8—C9—C100.7 (5)C16—C17—C18—N3−179.0 (3)
C8—C9—C10—C11−1.3 (5)O2—N3—C18—C19176.0 (3)
C8—C9—C10—C13−179.8 (3)O3—N3—C18—C19−4.9 (5)
C9—C10—C11—C120.7 (5)O2—N3—C18—C17−4.5 (5)
C13—C10—C11—C12179.1 (3)O3—N3—C18—C17174.6 (3)
C10—C11—C12—C70.5 (5)C17—C18—C19—C20−0.1 (5)
C8—C7—C12—C11−1.1 (5)N3—C18—C19—C20179.5 (3)
C6—C7—C12—C11179.0 (3)C16—C15—C20—C192.2 (5)
C14—N1—C13—O13.9 (5)N2—C15—C20—C19179.0 (3)
C14—N1—C13—C10−176.1 (3)C18—C19—C20—C15−1.3 (6)
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.861.902.633 (4)142
C20—H20···S10.932.553.186 (4)126
Ring 1Ring 2φdΔ
Cg1Cg1i0.03.991 (2)1.778
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2A⋯O10.861.902.633 (4)142
C20—H20⋯S10.932.553.186 (4)126
  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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

Authors:  Bohari M Yamin; M Asyikin M Arif
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2007-12-06

3.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  3 in total
  2 in total

1.  1-(Biphenyl-4-ylcarbon-yl)-3-(2-chloro-4-nitro-phen-yl)thio-urea.

Authors:  M Sukeri M Yusof; Bohari M Yamin; Nurziana Ngah
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-21

2.  4-Methyl-N-[2-(pyridin-2-yl)ethyl-carbamo-thio-yl]benzamide.

Authors:  Farook Adam; Nadiah Ameram; Naser Eltaher Eltayeb
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-07-31
  2 in total

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