Literature DB >> 22590357

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

M Sukeri M Yusof, Bohari M Yamin, Nurziana Ngah.   

Abstract

The benzene rings of the biphenyl group in the title compound, C(20)H(14)ClN(3)O(3)S, are nearly coplanar [maximum deviation = 0.20 (3) Å]. The mean plane of the biphenyl group forms a dihedral angle of 5.24 (7)° with the aromatic ring of the nitro-chloro-benzene group. Intra-molecular N-H⋯Cl, N-H⋯O and C-H⋯S hydrogen bonds stabilize the cis-trans conformation of the mol-ecule. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯S hydrogen bonds into mutually inter-woven corrugated layers parallel to (10-2).

Entities:  

Year:  2012        PMID： 22590357      PMCID： PMC3344595          DOI： 10.1107/S1600536812016686

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


Related literature

For a related structure, see: Yusof et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H14ClN3O3S M = 411.85 Monoclinic, a = 10.889 (2) Å b = 5.4502 (10) Å c = 30.532 (5) Å β = 99.202 (4)° V = 1788.6 (6) Å3 Z = 4 Mo Kα radiation μ = 0.36 mm−1 T = 298 K 0.35 × 0.13 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.885, T max = 0.972 9537 measured reflections 3154 independent reflections 2704 reflections with I > 2/s(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.137 S = 1.16 3154 reflections 253 parameters 3 restraints H-atom parameters constrained Δρmax = 0.25 e Å−3 Δρmin = −0.24 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 datablock(s) global, I. DOI: 10.1107/S1600536812016686/rz2737sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016686/rz2737Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812016686/rz2737Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H14ClN3O3SF(000) = 848
Mr = 411.85Dx = 1.529 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1235 reflections
a = 10.889 (2) Åθ = 1.9–25.0°
b = 5.4502 (10) ŵ = 0.36 mm−1
c = 30.532 (5) ÅT = 298 K
β = 99.202 (4)°Slab, yellow
V = 1788.6 (6) Å30.35 × 0.13 × 0.08 mm
Z = 4
Bruker SMART APEX CCD area-detector diffractometer3154 independent reflections
Radiation source: fine-focus sealed tube2704 reflections with I > 2/s(I)
Graphite monochromatorRint = 0.026
Detector resolution: 83.66 pixels mm-1θmax = 25.0°, θmin = 1.9°
ω scanh = −11→12
Absorption correction: multi-scan (SADABS; Bruker, 2000)k = −6→6
Tmin = 0.885, Tmax = 0.972l = −35→36
9537 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.16w = 1/[σ2(Fo2) + (0.0709P)2 + 0.5419P] where P = (Fo2 + 2Fc2)/3
3154 reflections(Δ/σ)max = 0.002
253 parametersΔρmax = 0.25 e Å−3
3 restraintsΔρmin = −0.24 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
S10.66457 (7)0.06984 (14)0.93137 (2)0.0553 (3)
Cl10.88661 (6)0.87141 (13)1.03030 (2)0.0511 (2)
O10.9472 (2)0.6794 (4)0.93384 (7)0.0691 (7)
O20.5004 (3)0.4603 (5)1.13921 (9)0.0849 (8)
O30.6132 (2)0.7850 (5)1.15220 (7)0.0701 (6)
N10.8315 (2)0.3541 (4)0.90589 (7)0.0449 (5)
H1A0.81620.26130.88290.054*
N20.7806 (2)0.4647 (4)0.97322 (7)0.0456 (5)
H2A0.83660.57310.97090.055*
N30.5772 (2)0.6060 (5)1.12973 (9)0.0559 (6)
C11.0767 (3)0.7043 (5)0.86344 (10)0.0538 (7)
H1B1.08560.82960.88440.065*
C21.1482 (3)0.7078 (5)0.83008 (9)0.0509 (7)
H2B1.20400.83590.82900.061*
C31.1390 (2)0.5250 (5)0.79806 (8)0.0374 (6)
C41.0527 (3)0.3419 (5)0.80119 (9)0.0520 (7)
H4A1.04320.21710.78010.062*
C50.9802 (3)0.3377 (5)0.83435 (9)0.0509 (7)
H5A0.92280.21190.83510.061*
C60.9919 (2)0.5184 (5)0.86650 (8)0.0394 (6)
C71.2173 (2)0.5270 (5)0.76232 (8)0.0393 (6)
C81.3045 (3)0.7076 (6)0.75971 (10)0.0609 (8)
H8A1.31530.83150.78090.073*
C91.3767 (3)0.7083 (7)0.72601 (11)0.0681 (9)
H9A1.43420.83330.72480.082*
C101.3638 (3)0.5275 (6)0.69487 (9)0.0551 (8)
H10A1.41270.52740.67250.066*
C111.2787 (3)0.3470 (7)0.69684 (11)0.0661 (9)
H11A1.26910.22280.67570.079*
C121.2060 (3)0.3469 (6)0.73013 (10)0.0570 (8)
H12A1.14810.22220.73080.068*
C130.9227 (2)0.5278 (5)0.90462 (9)0.0439 (6)
C140.7603 (2)0.3068 (5)0.93919 (8)0.0404 (6)
C150.7273 (2)0.4852 (5)1.01169 (8)0.0408 (6)
C160.6357 (3)0.3307 (6)1.02337 (10)0.0543 (7)
H16A0.60670.20021.00500.065*
C170.5876 (3)0.3692 (6)1.06191 (10)0.0547 (7)
H17A0.52740.26361.06960.066*
C180.6284 (2)0.5623 (5)1.08869 (9)0.0446 (6)
C190.7191 (2)0.7181 (5)1.07878 (8)0.0449 (6)
H19A0.74670.84851.09740.054*
C200.7686 (2)0.6773 (5)1.04071 (8)0.0396 (6)
U11U22U33U12U13U23
S10.0593 (5)0.0552 (5)0.0514 (4)−0.0271 (4)0.0085 (3)−0.0054 (3)
Cl10.0524 (4)0.0538 (4)0.0498 (4)−0.0219 (3)0.0157 (3)−0.0058 (3)
O10.0819 (15)0.0638 (14)0.0722 (14)−0.0380 (12)0.0450 (12)−0.0317 (12)
O20.0952 (18)0.0893 (18)0.0836 (16)−0.0164 (13)0.0550 (15)0.0070 (14)
O30.0645 (14)0.0899 (16)0.0605 (13)0.0008 (11)0.0238 (11)−0.0129 (12)
N10.0453 (12)0.0477 (13)0.0434 (12)−0.0120 (10)0.0128 (10)−0.0082 (10)
N20.0458 (13)0.0420 (12)0.0526 (13)−0.0151 (10)0.0190 (10)−0.0077 (11)
N30.0498 (14)0.0645 (16)0.0577 (14)0.0066 (11)0.0216 (11)0.0093 (11)
C10.0617 (18)0.0461 (17)0.0583 (17)−0.0176 (14)0.0241 (14)−0.0175 (14)
C20.0548 (17)0.0448 (16)0.0573 (17)−0.0188 (13)0.0219 (13)−0.0077 (13)
C30.0366 (13)0.0363 (13)0.0390 (13)0.0025 (10)0.0051 (10)0.0045 (11)
C40.0615 (18)0.0478 (17)0.0504 (16)−0.0162 (14)0.0201 (13)−0.0125 (13)
C50.0573 (17)0.0461 (16)0.0534 (16)−0.0211 (13)0.0216 (13)−0.0096 (13)
C60.0393 (13)0.0382 (14)0.0410 (13)−0.0018 (11)0.0076 (11)0.0008 (11)
C70.0386 (13)0.0429 (14)0.0361 (12)0.0016 (11)0.0049 (10)0.0066 (11)
C80.071 (2)0.061 (2)0.0552 (17)−0.0232 (16)0.0239 (15)−0.0135 (15)
C90.073 (2)0.075 (2)0.0625 (19)−0.0270 (18)0.0315 (16)−0.0033 (17)
C100.0517 (17)0.072 (2)0.0442 (15)0.0002 (15)0.0169 (13)0.0032 (15)
C110.070 (2)0.074 (2)0.0601 (18)−0.0131 (18)0.0278 (16)−0.0217 (17)
C120.0601 (18)0.0551 (18)0.0606 (17)−0.0152 (14)0.0240 (14)−0.0149 (15)
C130.0427 (14)0.0406 (15)0.0500 (15)−0.0056 (12)0.0118 (12)−0.0052 (13)
C140.0337 (13)0.0414 (15)0.0452 (14)−0.0030 (11)0.0036 (10)0.0034 (12)
C150.0375 (14)0.0404 (14)0.0461 (14)−0.0030 (11)0.0113 (11)0.0016 (12)
C160.0545 (17)0.0507 (17)0.0624 (18)−0.0163 (14)0.0236 (14)−0.0086 (14)
C170.0513 (16)0.0541 (18)0.0645 (18)−0.0134 (14)0.0265 (14)0.0032 (15)
C180.0389 (14)0.0507 (16)0.0463 (14)0.0028 (12)0.0133 (11)0.0062 (13)
C190.0425 (14)0.0482 (16)0.0441 (14)−0.0021 (12)0.0078 (11)0.0005 (12)
C200.0343 (13)0.0416 (15)0.0439 (13)−0.0056 (11)0.0097 (10)0.0027 (11)
S1—C141.653 (3)C5—H5A0.9300
Cl1—C201.733 (3)C6—C131.485 (4)
O1—C131.214 (3)C7—C81.379 (4)
O2—N31.221 (3)C7—C121.380 (4)
O3—N31.221 (3)C8—C91.391 (4)
N1—C131.377 (3)C8—H8A0.9300
N1—C141.397 (3)C9—C101.361 (5)
N1—H1A0.8600C9—H9A0.9300
N2—C141.340 (3)C10—C111.360 (5)
N2—C151.395 (3)C10—H10A0.9300
N2—H2A0.8600C11—C121.384 (4)
N3—C181.470 (4)C11—H11A0.9300
C1—C21.377 (4)C12—H12A0.9300
C1—C61.384 (4)C15—C161.395 (4)
C1—H1B0.9300C15—C201.398 (4)
C2—C31.388 (4)C16—C171.378 (4)
C2—H2B0.9300C16—H16A0.9300
C3—C41.385 (4)C17—C181.363 (4)
C3—C71.488 (3)C17—H17A0.9300
C4—C51.380 (4)C18—C191.373 (4)
C4—H4A0.9300C19—C201.375 (3)
C5—C61.382 (4)C19—H19A0.9300
C13—N1—C14129.3 (2)C8—C9—H9A119.7
C13—N1—H1A115.3C11—C10—C9119.2 (3)
C14—N1—H1A115.3C11—C10—H10A120.4
C14—N2—C15131.7 (2)C9—C10—H10A120.4
C14—N2—H2A114.1C10—C11—C12120.4 (3)
C15—N2—H2A114.1C10—C11—H11A119.8
O2—N3—O3123.9 (3)C12—C11—H11A119.8
O2—N3—C18117.7 (3)C7—C12—C11121.8 (3)
O3—N3—C18118.5 (2)C7—C12—H12A119.1
C2—C1—C6121.5 (3)C11—C12—H12A119.1
C2—C1—H1B119.3O1—C13—N1121.5 (2)
C6—C1—H1B119.3O1—C13—C6121.3 (2)
C1—C2—C3121.7 (2)N1—C13—C6117.2 (2)
C1—C2—H2B119.2N2—C14—N1113.8 (2)
C3—C2—H2B119.2N2—C14—S1129.5 (2)
C4—C3—C2116.2 (2)N1—C14—S1116.71 (19)
C4—C3—C7122.0 (2)C16—C15—N2125.3 (2)
C2—C3—C7121.8 (2)C16—C15—C20117.4 (2)
C5—C4—C3122.5 (3)N2—C15—C20117.3 (2)
C5—C4—H4A118.8C17—C16—C15120.7 (3)
C3—C4—H4A118.8C17—C16—H16A119.6
C4—C5—C6120.7 (2)C15—C16—H16A119.6
C4—C5—H5A119.7C18—C17—C16119.9 (3)
C6—C5—H5A119.7C18—C17—H17A120.1
C5—C6—C1117.4 (2)C16—C17—H17A120.1
C5—C6—C13125.5 (2)C17—C18—C19121.5 (3)
C1—C6—C13117.1 (2)C17—C18—N3120.3 (3)
C8—C7—C12116.7 (2)C19—C18—N3118.2 (3)
C8—C7—C3121.9 (2)C18—C19—C20118.6 (3)
C12—C7—C3121.4 (2)C18—C19—H19A120.7
C7—C8—C9121.4 (3)C20—C19—H19A120.7
C7—C8—H8A119.3C19—C20—C15121.8 (2)
C9—C8—H8A119.3C19—C20—Cl1117.3 (2)
C10—C9—C8120.5 (3)C15—C20—Cl1120.91 (19)
C10—C9—H9A119.7
C6—C1—C2—C3−0.2 (5)C5—C6—C13—N1−6.0 (4)
C1—C2—C3—C41.0 (4)C1—C6—C13—N1175.1 (3)
C1—C2—C3—C7−179.3 (3)C15—N2—C14—N1178.0 (2)
C2—C3—C4—C5−0.7 (4)C15—N2—C14—S1−1.8 (4)
C7—C3—C4—C5179.6 (3)C13—N1—C14—N24.2 (4)
C3—C4—C5—C6−0.5 (5)C13—N1—C14—S1−175.9 (2)
C4—C5—C6—C11.3 (4)C14—N2—C15—C160.8 (5)
C4—C5—C6—C13−177.5 (3)C14—N2—C15—C20−178.8 (3)
C2—C1—C6—C5−0.9 (5)N2—C15—C16—C17−179.0 (3)
C2—C1—C6—C13178.0 (3)C20—C15—C16—C170.6 (4)
C4—C3—C7—C8−179.0 (3)C15—C16—C17—C181.0 (5)
C2—C3—C7—C81.3 (4)C16—C17—C18—C19−1.6 (5)
C4—C3—C7—C120.9 (4)C16—C17—C18—N3179.6 (3)
C2—C3—C7—C12−178.8 (3)O2—N3—C18—C171.9 (4)
C12—C7—C8—C90.5 (5)O3—N3—C18—C17−177.8 (3)
C3—C7—C8—C9−179.7 (3)O2—N3—C18—C19−176.9 (3)
C7—C8—C9—C10−0.8 (6)O3—N3—C18—C193.3 (4)
C8—C9—C10—C110.6 (5)C17—C18—C19—C200.5 (4)
C9—C10—C11—C12−0.1 (5)N3—C18—C19—C20179.3 (2)
C8—C7—C12—C110.0 (5)C18—C19—C20—C151.2 (4)
C3—C7—C12—C11−179.8 (3)C18—C19—C20—Cl1−177.9 (2)
C10—C11—C12—C7−0.2 (5)C16—C15—C20—C19−1.7 (4)
C14—N1—C13—O1−4.7 (5)N2—C15—C20—C19177.9 (2)
C14—N1—C13—C6173.9 (2)C16—C15—C20—Cl1177.3 (2)
C5—C6—C13—O1172.6 (3)N2—C15—C20—Cl1−3.1 (3)
C1—C6—C13—O1−6.2 (4)
D—H···AD—HH···AD···AD—H···A
N2—H2A···Cl10.862.432.938 (2)118
N2—H2A···O10.861.872.608 (3)143
C16—H16A···S10.932.533.208 (3)130
C10—H10A···O3i0.932.573.354 (4)142
C17—H17A···S1ii0.932.773.673 (3)165
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2A⋯Cl10.862.432.938 (2)118
N2—H2A⋯O10.861.872.608 (3)143
C16—H16A⋯S10.932.533.208 (3)130
C10—H10A⋯O3i0.932.573.354 (4)142
C17—H17A⋯S1ii0.932.773.673 (3)165

Symmetry codes: (i) ; (ii) .

  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.  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

3.  Structure validation in chemical crystallography.

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

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