Literature DB >> 22090990

3-(3-Meth-oxy-benzo-yl)-1,1-diphenyl-thio-urea.

Mohd Faizal Md Nasir, Ibrahim N Hassan, Bohari M Yamin, W R W Daud, Mohammad B Kassim.   

Abstract

The thiono and carbonyl groups in the title compound, C(21)H(18)N(2)O(2)S, adopt an anti disposition with respect to the central C-N bond. The diphenyl-amine rings are twisted relative to each other by a dihedral angle of 82.55 (10)°. The 3-meth-oxy-benzoyl fragment is twisted relative to one of the diphenyl-amine rings, forming a dihedral angle of 74.04 (9)°. In the crystal, pairs of inter-molecular N-H⋯S hydrogen bonds link the mol-ecules into centrosymmetric dimers, forming columns parallel to the a axis.

Entities:  

Year:  2011        PMID： 22090990      PMCID： PMC3212333          DOI： 10.1107/S1600536811025785

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


Related literature

For related structures and background references, see: Al-abbasi et al. (2010 ▶); Al-abbasi & Kassim (2011 ▶); Md Nasir et al. (2011 ▶). For metal complexes of benzoyl­thio­ureas, see: Circu et al. (2009 ▶); Weiqun et al. (2005 ▶). For the synthetic procedure, see: Hassan et al. (2008 ▶). For a standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H18N2O2S M = 362.43 Triclinic, a = 6.056 (3) Å b = 12.895 (7) Å c = 13.344 (7) Å α = 112.796 (9)° β = 100.336 (10)° γ = 97.951 (10)° V = 920.0 (8) Å3 Z = 2 Mo Kα radiation μ = 0.19 mm−1 T = 298 K 0.52 × 0.23 × 0.03 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.906, T max = 0.994 10189 measured reflections 3612 independent reflections 2663 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.110 S = 1.04 3612 reflections 240 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.17 e Å−3 Δρmin = −0.27 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 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811025785/jh2306sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025785/jh2306Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811025785/jh2306Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H18N2O2SZ = 2
Mr = 362.43F(000) = 380
Triclinic, P1Dx = 1.308 Mg m−3
Hall symbol: -P 1Melting point = 412.15–410.15 K
a = 6.056 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.895 (7) ÅCell parameters from 3612 reflections
c = 13.344 (7) Åθ = 6.4–55.2°
α = 112.796 (9)°µ = 0.19 mm−1
β = 100.336 (10)°T = 298 K
γ = 97.951 (10)°Plate, yellow
V = 920.0 (8) Å30.52 × 0.23 × 0.03 mm
Bruker SMART APEX CCD area-detector diffractometer3612 independent reflections
Radiation source: fine-focus sealed tube2663 reflections with I > 2σ(I)
graphiteRint = 0.029
ω scanθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −7→7
Tmin = 0.906, Tmax = 0.994k = −15→15
10189 measured reflectionsl = −16→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0578P)2 + 0.1546P] where P = (Fo2 + 2Fc2)/3
3612 reflections(Δ/σ)max < 0.001
240 parametersΔρmax = 0.17 e Å−3
0 restraintsΔρmin = −0.27 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
S10.28578 (10)0.32442 (4)0.43411 (4)0.05684 (19)
O10.0958 (3)0.92764 (11)0.40494 (14)0.0667 (4)
O2−0.0666 (2)0.49768 (10)0.27758 (12)0.0554 (4)
N10.2897 (3)0.47668 (11)0.34630 (12)0.0403 (4)
N20.0990 (2)0.28974 (11)0.22465 (10)0.0372 (3)
C60.4600 (3)0.67429 (15)0.30353 (15)0.0458 (4)
H60.54080.61640.28210.055*
C50.5442 (3)0.78217 (16)0.30918 (17)0.0504 (5)
H50.68170.79620.28980.060*
C40.4287 (3)0.86899 (15)0.34293 (15)0.0458 (4)
H40.48890.94130.34710.055*
C30.2235 (3)0.84874 (14)0.37065 (15)0.0438 (4)
C20.1354 (3)0.74050 (14)0.36416 (14)0.0430 (4)
H2−0.00310.72640.38270.052*
C10.2519 (3)0.65424 (13)0.33049 (13)0.0380 (4)
C210.1482 (4)1.03154 (16)0.39139 (19)0.0595 (5)
H21A0.29921.07540.43780.089*
H21B0.03661.07620.41320.089*
H21C0.14431.01320.31410.089*
C70.1389 (3)0.53717 (14)0.31542 (14)0.0405 (4)
C80.2192 (3)0.36345 (13)0.33048 (13)0.0376 (4)
C90.1204 (3)0.31150 (13)0.12858 (13)0.0369 (4)
C14−0.0742 (3)0.29310 (16)0.04667 (14)0.0476 (4)
H14−0.21920.26590.05290.057*
C13−0.0526 (4)0.31537 (19)−0.04475 (16)0.0610 (6)
H13−0.18360.3029−0.10020.073*
C120.1610 (4)0.35575 (19)−0.05447 (17)0.0618 (6)
H120.17450.3719−0.11550.074*
C110.3535 (4)0.37199 (18)0.02626 (18)0.0579 (5)
H110.49830.39870.01950.070*
C100.3355 (3)0.34923 (15)0.11738 (15)0.0464 (4)
H100.46750.35920.17120.056*
C15−0.0664 (3)0.18826 (13)0.20578 (13)0.0388 (4)
C16−0.2480 (3)0.20071 (17)0.25501 (16)0.0523 (5)
H16−0.25820.27360.30350.063*
C17−0.4148 (4)0.1046 (2)0.2320 (2)0.0697 (6)
H17−0.53740.11250.26540.084*
C18−0.4001 (4)−0.0022 (2)0.16034 (19)0.0757 (8)
H18−0.5141−0.06680.14420.091*
C19−0.2184 (4)−0.01469 (17)0.11210 (17)0.0691 (7)
H19−0.2089−0.08790.06400.083*
C20−0.0481 (4)0.08113 (14)0.13453 (14)0.0505 (5)
H200.07560.07290.10200.061*
H1A0.416 (3)0.5170 (16)0.3974 (17)0.049 (5)*
U11U22U33U12U13U23
S10.0816 (4)0.0375 (2)0.0398 (3)−0.0063 (2)−0.0094 (2)0.02171 (19)
O10.0816 (11)0.0378 (7)0.1021 (12)0.0228 (7)0.0492 (9)0.0372 (7)
O20.0428 (8)0.0374 (7)0.0779 (9)0.0029 (6)0.0069 (7)0.0217 (6)
N10.0461 (9)0.0274 (7)0.0387 (7)−0.0018 (6)−0.0051 (7)0.0153 (6)
N20.0446 (8)0.0302 (7)0.0328 (7)0.0003 (6)0.0040 (6)0.0142 (5)
C60.0488 (11)0.0418 (9)0.0496 (10)0.0113 (8)0.0086 (8)0.0238 (8)
C50.0430 (10)0.0521 (11)0.0630 (12)0.0058 (9)0.0131 (9)0.0333 (9)
C40.0488 (11)0.0375 (9)0.0517 (10)0.0015 (8)0.0055 (8)0.0253 (8)
C30.0518 (11)0.0335 (9)0.0469 (9)0.0085 (8)0.0110 (8)0.0188 (7)
C20.0461 (10)0.0367 (9)0.0495 (10)0.0072 (8)0.0132 (8)0.0218 (8)
C10.0430 (10)0.0328 (8)0.0361 (8)0.0026 (7)0.0026 (7)0.0176 (7)
C210.0784 (15)0.0376 (10)0.0712 (13)0.0151 (10)0.0196 (11)0.0313 (10)
C70.0489 (11)0.0310 (8)0.0379 (8)0.0046 (7)0.0078 (7)0.0137 (7)
C80.0401 (9)0.0309 (8)0.0372 (8)0.0020 (7)0.0029 (7)0.0147 (7)
C90.0448 (10)0.0315 (8)0.0334 (8)0.0053 (7)0.0072 (7)0.0152 (6)
C140.0459 (11)0.0524 (10)0.0402 (9)0.0039 (8)0.0045 (8)0.0205 (8)
C130.0669 (14)0.0732 (13)0.0408 (10)0.0146 (11)0.0008 (9)0.0283 (10)
C120.0808 (16)0.0711 (14)0.0466 (11)0.0179 (12)0.0230 (11)0.0353 (10)
C110.0609 (13)0.0614 (12)0.0640 (12)0.0120 (10)0.0276 (10)0.0350 (10)
C100.0463 (11)0.0460 (10)0.0472 (10)0.0078 (8)0.0090 (8)0.0223 (8)
C150.0432 (10)0.0341 (8)0.0340 (8)−0.0015 (7)0.0017 (7)0.0162 (7)
C160.0512 (12)0.0517 (11)0.0542 (11)0.0064 (9)0.0130 (9)0.0247 (9)
C170.0547 (13)0.0831 (16)0.0705 (14)−0.0078 (12)0.0141 (11)0.0403 (13)
C180.0862 (17)0.0643 (14)0.0560 (12)−0.0330 (12)0.0002 (12)0.0286 (11)
C190.1047 (19)0.0375 (10)0.0451 (11)−0.0142 (11)0.0102 (12)0.0110 (8)
C200.0684 (13)0.0364 (9)0.0386 (9)0.0007 (9)0.0121 (9)0.0118 (7)
S1—C81.6503 (17)C21—H21C0.9600
O1—C31.351 (2)C9—C141.378 (2)
O1—C211.421 (2)C9—C101.381 (3)
O2—C71.210 (2)C14—C131.381 (3)
N1—C81.384 (2)C14—H140.9300
N1—C71.387 (2)C13—C121.373 (3)
N1—H1A0.87 (2)C13—H130.9300
N2—C81.352 (2)C12—C111.368 (3)
N2—C91.438 (2)C12—H120.9300
N2—C151.439 (2)C11—C101.375 (3)
C6—C51.382 (2)C11—H110.9300
C6—C11.389 (3)C10—H100.9300
C6—H60.9300C15—C201.374 (3)
C5—C41.373 (3)C15—C161.376 (3)
C5—H50.9300C16—C171.377 (3)
C4—C31.378 (3)C16—H160.9300
C4—H40.9300C17—C181.365 (4)
C3—C21.387 (2)C17—H170.9300
C2—C11.371 (3)C18—C191.369 (4)
C2—H20.9300C18—H180.9300
C1—C71.489 (2)C19—C201.389 (3)
C21—H21A0.9600C19—H190.9300
C21—H21B0.9600C20—H200.9300
C3—O1—C21118.49 (16)C14—C9—C10119.92 (16)
C8—N1—C7122.68 (15)C14—C9—N2119.86 (15)
C8—N1—H1A116.5 (13)C10—C9—N2120.21 (15)
C7—N1—H1A117.1 (13)C9—C14—C13119.56 (18)
C8—N2—C9122.38 (13)C9—C14—H14120.2
C8—N2—C15119.92 (13)C13—C14—H14120.2
C9—N2—C15117.62 (12)C12—C13—C14120.52 (19)
C5—C6—C1118.54 (17)C12—C13—H13119.7
C5—C6—H6120.7C14—C13—H13119.7
C1—C6—H6120.7C11—C12—C13119.54 (18)
C4—C5—C6121.22 (18)C11—C12—H12120.2
C4—C5—H5119.4C13—C12—H12120.2
C6—C5—H5119.4C12—C11—C10120.76 (19)
C5—C4—C3119.88 (16)C12—C11—H11119.6
C5—C4—H4120.1C10—C11—H11119.6
C3—C4—H4120.1C11—C10—C9119.66 (18)
O1—C3—C4124.89 (15)C11—C10—H10120.2
O1—C3—C2115.53 (16)C9—C10—H10120.2
C4—C3—C2119.57 (17)C20—C15—C16120.88 (16)
C1—C2—C3120.20 (17)C20—C15—N2119.82 (16)
C1—C2—H2119.9C16—C15—N2119.20 (16)
C3—C2—H2119.9C15—C16—C17119.6 (2)
C2—C1—C6120.58 (15)C15—C16—H16120.2
C2—C1—C7117.72 (16)C17—C16—H16120.2
C6—C1—C7121.53 (16)C18—C17—C16120.1 (2)
O1—C21—H21A109.5C18—C17—H17120.0
O1—C21—H21B109.5C16—C17—H17120.0
H21A—C21—H21B109.5C17—C18—C19120.30 (19)
O1—C21—H21C109.5C17—C18—H18119.9
H21A—C21—H21C109.5C19—C18—H18119.9
H21B—C21—H21C109.5C18—C19—C20120.5 (2)
O2—C7—N1123.01 (15)C18—C19—H19119.8
O2—C7—C1122.65 (16)C20—C19—H19119.8
N1—C7—C1114.33 (15)C15—C20—C19118.6 (2)
N2—C8—N1114.68 (14)C15—C20—H20120.7
N2—C8—S1124.04 (12)C19—C20—H20120.7
N1—C8—S1121.26 (12)
D—H···AD—HH···AD···AD—H···A
N1—H1A···S1i0.87 (2)2.54 (2)3.380 (2)163.6 (17)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1A⋯S1i0.87 (2)2.54 (2)3.380 (2)163.6 (17)

Symmetry code: (i) .

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