Literature DB >> 21202302

(R)-1-(4-Bromo-benzo-yl)-4-(1-phenyl-prop-yl)thio-semicarbazide.

Monazza Serwer, M Khawar Rauf, Masahiro Ebihara, Shahid Hameed.   

Abstract

The title compound, C(17)H(18)BrN(3)OS, is an important inter-mediate for the synthesis of biologically active heterocyclic compounds. The thio-urea group is approximately planar. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen-bonding inter-actions.

Entities:  

Year:  2008        PMID： 21202302      PMCID： PMC2961238          DOI： 10.1107/S1600536808006806

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


Related literature

For related literature, see: Akhtar et al. (2006 ▶, 2007 ▶); Cardia et al. (2006 ▶); Dolman et al. (2006 ▶); Hassan et al. (2006 ▶); Jalilian et al. (2000 ▶); Kucukguzel et al. (2006 ▶); Mohareb et al. (2007 ▶); n class="Gene">Singh et al. (2003 ▶, 2005 ▶).

Experimental

Crystal data

C17H18BrN3OS M = 392.31 Orthorhombic, a = 6.263 (3) Å b = 9.698 (5) Å c = 27.651 (15) Å V = 1679.5 (15) Å3 Z = 4 Mo Kα radiation μ = 2.58 mm−1 T = 123 (2) K 0.30 × 0.25 × 0.20 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer Absorption correction: integration (NUMABS; Higashi, 1999 ▶) T min = 0.512, T max = 0.626 13732 measured reflections 3824 independent reflections 3516 reflections with I > 2σ(I) R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.074 S = 1.13 3824 reflections 219 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.34 e Å−3 Δρmin = −0.35 e Å−3 Absolute structure: Flack (1983 ▶), 1584 Friedel pairs Flack parameter: 0.020 (10) Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and TEXSAN. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006806/hg2385sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006806/hg2385Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H18BrN3OSF000 = 800
Mr = 392.31Dx = 1.552 Mg m−3
Orthorhombic, P212121Mo Kα radiation λ = 0.71070 Å
Hall symbol: P 2ac 2abCell parameters from 4820 reflections
a = 6.263 (3) Åθ = 3.1–27.5º
b = 9.698 (5) ŵ = 2.58 mm−1
c = 27.651 (15) ÅT = 123 (2) K
V = 1679.5 (15) Å3Block, colourles
Z = 40.30 × 0.25 × 0.20 mm
Rigaku/MSC Mercury CCD diffractometer3824 independent reflections
Radiation source: fine-focus sealed tube3516 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.057
T = 123(2) Kθmax = 27.5º
ω scansθmin = 3.1º
Absorption correction: integration(NUMABS; Higashi, 1999)h = −8→8
Tmin = 0.512, Tmax = 0.627k = −12→8
13732 measured reflectionsl = −26→35
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full  w = 1/[σ2(Fo2) + 1.3691P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.048(Δ/σ)max < 0.001
wR(F2) = 0.074Δρmax = 0.34 e Å−3
S = 1.13Δρmin = −0.35 e Å−3
3824 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
219 parametersExtinction coefficient: 0.0018 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1584 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.020 (10)
Hydrogen site location: inferred from neighbouring sites
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
C10.0742 (6)0.2098 (3)0.24009 (12)0.0141 (8)
O10.0089 (4)0.0922 (2)0.23367 (10)0.0260 (7)
N1−0.0306 (5)0.3005 (3)0.26956 (12)0.0144 (7)
H10.006 (6)0.384 (4)0.2666 (13)0.017*
C2−0.2924 (6)0.2804 (3)0.33209 (13)0.0124 (8)
S1−0.55059 (15)0.30911 (9)0.34643 (4)0.0169 (2)
N2−0.2383 (5)0.2701 (3)0.28467 (12)0.0144 (7)
H2−0.319 (7)0.288 (4)0.2668 (15)0.017*
N3−0.1369 (5)0.2639 (3)0.36436 (12)0.0146 (6)
H3−0.024 (6)0.254 (3)0.3547 (15)0.017*
C30.2725 (6)0.2613 (3)0.21649 (13)0.0134 (8)
C40.3408 (6)0.3985 (4)0.21787 (13)0.0156 (8)
H40.26250.46430.23610.019*
C50.5216 (6)0.4390 (3)0.19285 (14)0.0171 (8)
H50.56810.53220.19390.020*
C60.6334 (7)0.3426 (3)0.16636 (12)0.0153 (7)
C70.5710 (6)0.2056 (4)0.16486 (13)0.0197 (8)
H70.65080.14010.14680.024*
C80.3915 (7)0.1659 (3)0.18998 (13)0.0169 (8)
H80.34790.07210.18930.020*
Br10.87772 (7)0.39971 (4)0.131114 (15)0.02482 (12)
C9−0.1593 (6)0.2802 (3)0.41665 (12)0.0152 (8)
H9−0.30330.32170.42240.018*
C10−0.1581 (6)0.1398 (3)0.44199 (13)0.0154 (8)
C11−0.3136 (6)0.0440 (3)0.42905 (14)0.0207 (9)
H11−0.41710.06740.40530.025*
C12−0.3188 (7)−0.0852 (4)0.45040 (15)0.0258 (10)
H12−0.4244−0.15030.44100.031*
C13−0.1711 (7)−0.1193 (4)0.48521 (14)0.0273 (10)
H13−0.1748−0.20780.49990.033*
C14−0.0166 (7)−0.0245 (4)0.49888 (16)0.0305 (11)
H140.0848−0.04750.52310.037*
C15−0.0110 (6)0.1039 (4)0.47705 (14)0.0231 (9)
H150.09560.16830.48630.028*
C160.0052 (6)0.3842 (4)0.43521 (13)0.0200 (8)
H16A0.15060.34750.42960.024*
H16B−0.01370.39660.47050.024*
C17−0.0165 (7)0.5243 (4)0.41003 (15)0.0276 (10)
H17A0.02090.51470.37580.041*
H17B0.07980.59090.42540.041*
H17C−0.16410.55690.41290.041*
U11U22U33U12U13U23
C10.017 (2)0.0147 (16)0.0109 (19)0.0004 (14)0.0000 (16)0.0045 (13)
O10.0226 (16)0.0156 (12)0.0397 (18)−0.0052 (12)0.0131 (13)−0.0043 (12)
N10.0114 (16)0.0133 (13)0.0185 (19)−0.0054 (12)0.0049 (14)0.0010 (12)
C20.0131 (19)0.0096 (15)0.015 (2)−0.0006 (13)0.0013 (16)−0.0013 (13)
S10.0102 (5)0.0220 (4)0.0184 (5)0.0014 (4)0.0029 (4)0.0007 (4)
N20.0078 (17)0.0215 (16)0.0140 (19)−0.0001 (13)−0.0027 (14)0.0057 (13)
N30.0102 (15)0.0230 (13)0.0105 (16)0.0013 (12)0.0013 (17)−0.0019 (12)
C30.0120 (19)0.0140 (16)0.014 (2)0.0009 (13)−0.0015 (16)0.0044 (13)
C40.015 (2)0.0156 (15)0.0165 (19)0.0032 (17)0.0005 (16)0.0038 (15)
C50.018 (2)0.0155 (17)0.018 (2)−0.0002 (14)−0.0004 (18)0.0023 (14)
C60.0116 (18)0.0256 (16)0.0087 (18)0.0002 (15)0.0002 (18)0.0040 (13)
C70.020 (2)0.0242 (17)0.015 (2)0.0037 (15)0.0044 (17)−0.0027 (15)
C80.016 (2)0.0158 (15)0.019 (2)−0.0009 (15)0.0043 (19)0.0004 (13)
Br10.01688 (19)0.03197 (19)0.0256 (2)−0.00092 (17)0.0097 (2)0.00672 (18)
C90.015 (2)0.0230 (17)0.0078 (19)−0.0003 (15)0.0031 (16)−0.0007 (13)
C100.018 (2)0.0194 (16)0.0090 (18)0.0018 (14)0.0014 (17)−0.0006 (12)
C110.020 (2)0.0270 (18)0.015 (2)−0.0036 (15)−0.0038 (17)0.0045 (15)
C120.028 (3)0.028 (2)0.021 (2)−0.0071 (18)0.0013 (18)−0.0019 (17)
C130.038 (3)0.0230 (19)0.021 (2)0.0071 (18)0.005 (2)0.0009 (16)
C140.035 (3)0.033 (2)0.023 (3)0.0116 (19)−0.011 (2)0.0005 (18)
C150.027 (2)0.0242 (18)0.018 (2)−0.0021 (19)−0.0045 (18)0.0018 (18)
C160.020 (2)0.0275 (18)0.013 (2)−0.0051 (16)0.0007 (16)−0.0030 (16)
C170.032 (3)0.030 (2)0.021 (2)−0.0109 (18)0.004 (2)0.0027 (17)
C1—O11.224 (4)C8—H80.9500
C1—N11.367 (4)C9—C161.531 (5)
C1—C31.489 (5)C9—C101.532 (4)
N1—N21.397 (4)C9—H91.0000
N1—H10.84 (4)C10—C151.382 (5)
C2—N31.330 (5)C10—C111.393 (5)
C2—N21.358 (5)C11—C121.386 (5)
C2—S11.688 (4)C11—H110.9500
N2—H20.73 (4)C12—C131.376 (6)
N3—C91.461 (5)C12—H120.9500
N3—H30.76 (4)C13—C141.387 (6)
C3—C81.396 (5)C13—H130.9500
C3—C41.398 (5)C14—C151.384 (5)
C4—C51.384 (5)C14—H140.9500
C4—H40.9500C15—H150.9500
C5—C61.379 (5)C16—C171.532 (5)
C5—H50.9500C16—H16A0.9900
C6—C71.386 (5)C16—H16B0.9900
C6—Br11.897 (4)C17—H17A0.9800
C7—C81.376 (5)C17—H17B0.9800
C7—H70.9500C17—H17C0.9800
O1—C1—N1121.7 (3)C16—C9—C10115.4 (3)
O1—C1—C3121.8 (3)N3—C9—H9106.8
N1—C1—C3116.5 (3)C16—C9—H9106.8
C1—N1—N2119.3 (3)C10—C9—H9106.8
C1—N1—H1115 (3)C15—C10—C11118.6 (3)
N2—N1—H1119 (3)C15—C10—C9123.3 (3)
N3—C2—N2117.1 (3)C11—C10—C9118.2 (3)
N3—C2—S1124.3 (3)C12—C11—C10120.7 (4)
N2—C2—S1118.6 (3)C12—C11—H11119.6
C2—N2—N1120.4 (3)C10—C11—H11119.6
C2—N2—H2118 (3)C13—C12—C11120.0 (4)
N1—N2—H2113 (3)C13—C12—H12120.0
C2—N3—C9125.5 (3)C11—C12—H12120.0
C2—N3—H3117 (3)C12—C13—C14120.0 (4)
C9—N3—H3117 (3)C12—C13—H13120.0
C8—C3—C4118.8 (3)C14—C13—H13120.0
C8—C3—C1117.0 (3)C15—C14—C13119.7 (4)
C4—C3—C1124.2 (3)C15—C14—H14120.2
C5—C4—C3120.4 (3)C13—C14—H14120.2
C5—C4—H4119.8C10—C15—C14121.1 (4)
C3—C4—H4119.8C10—C15—H15119.5
C6—C5—C4119.2 (3)C14—C15—H15119.5
C6—C5—H5120.4C9—C16—C17111.8 (3)
C4—C5—H5120.4C9—C16—H16A109.3
C5—C6—C7121.5 (4)C17—C16—H16A109.3
C5—C6—Br1119.0 (3)C9—C16—H16B109.3
C7—C6—Br1119.5 (3)C17—C16—H16B109.3
C8—C7—C6118.9 (3)H16A—C16—H16B107.9
C8—C7—H7120.5C16—C17—H17A109.5
C6—C7—H7120.5C16—C17—H17B109.5
C7—C8—C3121.0 (3)H17A—C17—H17B109.5
C7—C8—H8119.5C16—C17—H17C109.5
C3—C8—H8119.5H17A—C17—H17C109.5
N3—C9—C16109.8 (3)H17B—C17—H17C109.5
N3—C9—C10110.8 (3)
O1—C1—N1—N2−13.7 (5)C4—C3—C8—C7−1.1 (6)
C3—C1—N1—N2166.7 (3)C1—C3—C8—C7176.6 (3)
N3—C2—N2—N1−26.7 (4)C2—N3—C9—C16−125.2 (3)
S1—C2—N2—N1154.7 (2)C2—N3—C9—C10106.1 (4)
C1—N1—N2—C2131.2 (3)N3—C9—C10—C15121.4 (4)
N2—C2—N3—C9175.6 (3)C16—C9—C10—C15−4.2 (5)
S1—C2—N3—C9−6.0 (4)N3—C9—C10—C11−58.7 (4)
O1—C1—C3—C8−5.4 (5)C16—C9—C10—C11175.7 (3)
N1—C1—C3—C8174.2 (3)C15—C10—C11—C12−0.8 (6)
O1—C1—C3—C4172.1 (3)C9—C10—C11—C12179.3 (3)
N1—C1—C3—C4−8.3 (5)C10—C11—C12—C130.8 (6)
C8—C3—C4—C50.8 (5)C11—C12—C13—C14−0.1 (6)
C1—C3—C4—C5−176.7 (3)C12—C13—C14—C15−0.5 (6)
C3—C4—C5—C60.2 (5)C11—C10—C15—C140.2 (6)
C4—C5—C6—C7−1.1 (6)C9—C10—C15—C14−180.0 (4)
C4—C5—C6—Br1178.7 (3)C13—C14—C15—C100.5 (6)
C5—C6—C7—C80.8 (6)N3—C9—C16—C1757.4 (4)
Br1—C6—C7—C8−179.0 (3)C10—C9—C16—C17−176.5 (3)
C6—C7—C8—C30.3 (6)
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.84 (4)2.03 (4)2.834 (4)161 (4)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O1i0.84 (4)2.03 (4)2.834 (4)161 (4)

Symmetry code: (i) .

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