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In the crystal structure of the title compound, C20H23BrN2OS, the dihedral angle between the two aromatic rings is 72.51 (6)°. The crystal packing shows dimers formed by inter­molecular N—H...S hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019143/bt2094sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019143/bt2094Isup2.hkl
Contains datablock I

CCDC reference: 610724

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.034
  • wR factor = 0.087
  • Data-to-parameter ratio = 20.8

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-(3-Bromophenyl)-3-[3-(4-isobutylphenyl)propanoyl]thiourea top
Crystal data top
C20H23BrN2OSF(000) = 864
Mr = 419.37Dx = 1.431 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6541 reflections
a = 14.4471 (8) Åθ = 2.3–28.4°
b = 7.7226 (4) ŵ = 2.23 mm1
c = 17.4659 (10) ÅT = 120 K
β = 92.406 (1)°Prism, colourless
V = 1946.94 (18) Å30.42 × 0.40 × 0.28 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4711 independent reflections
Radiation source: sealed tube4100 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 28.1°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1919
Tmin = 0.423, Tmax = 0.534k = 1010
18926 measured reflectionsl = 2123
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: difference Fourier map
wR(F2) = 0.087H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0454P)2 + 1.0691P]
where P = (Fo2 + 2Fc2)/3
4711 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.98 e Å3
0 restraintsΔρmin = 0.92 e Å3
Special details top

Experimental. 1H NMR (CDCl3, δ, p.p.m.): 93 [6H, d, (CH3)2CH, J = 6.6 Hz], 1.58 (3H, d, ArCHCH3, J = 7.2 Hz), 1.84–1.90 (1H, p, ArCH3CH, J = 6.9 Hz), 2.49 [2H, d, (CH3)2CHCH2Ar, J = 7.2 Hz], 3.66–3.73 [1H, q, (CH3)2CH, J = 6.9 Hz], 7.1–7.29 (5H, m, arom.), 7.74 (1H, s, arom.), 7.6 (1H, s, arom.), 8.69 (1H, s, broad, NH), 12.43 (1H, s, broad, NH); 13C NMR (CDCl3, δ, p.p.m.): 23.9 (CH3), 126.2 (4CH), 129.0 (2CH), 129.20 (2CH), 130.7 (C), 132.1 (C), 134.8 (C), 142.3 (C), 168.1 (CO), 178.4 (C S). EIMS m/e: 418, 420, 168.9,126, 119, 91, 64.9.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.765717 (16)1.51921 (3)0.616164 (14)0.03575 (9)
S10.50010 (3)0.69573 (6)0.58567 (3)0.02356 (11)
O10.69087 (10)0.88850 (17)0.40328 (8)0.0282 (3)
N10.60977 (10)0.94644 (19)0.53119 (9)0.0187 (3)
H10.64140.97600.49130.022*
N20.59817 (10)0.69455 (19)0.46234 (8)0.0174 (3)
H2A0.57430.59010.45770.021*
C10.60844 (12)1.0752 (2)0.58878 (10)0.0175 (3)
C20.67037 (12)1.2112 (2)0.57819 (11)0.0196 (3)
H20.70671.21390.53410.024*
C30.67855 (13)1.3410 (2)0.63190 (11)0.0226 (4)
C40.62605 (14)1.3421 (3)0.69643 (11)0.0245 (4)
H40.63311.43130.73370.029*
C50.56289 (13)1.2089 (2)0.70492 (11)0.0238 (4)
H50.52531.20900.74820.029*
C60.55299 (12)1.0752 (2)0.65198 (11)0.0204 (4)
H60.50910.98550.65880.024*
C70.57226 (11)0.7887 (2)0.52577 (10)0.0171 (3)
C80.65648 (12)0.7437 (2)0.40581 (10)0.0189 (3)
C90.67799 (12)0.6042 (2)0.34830 (10)0.0180 (3)
H90.62360.52440.34250.022*
C100.69605 (13)0.6850 (3)0.27030 (11)0.0225 (4)
H10A0.64130.75050.25210.034*
H10B0.70890.59320.23350.034*
H10C0.74950.76300.27530.034*
C110.76212 (13)0.5010 (2)0.37741 (10)0.0180 (3)
C120.84612 (12)0.5831 (2)0.39492 (11)0.0211 (4)
H120.84920.70600.39460.025*
C130.92551 (13)0.4871 (2)0.41286 (11)0.0223 (4)
H130.98240.54540.42410.027*
C140.92297 (12)0.3075 (2)0.41462 (10)0.0207 (4)
C150.83794 (13)0.2255 (2)0.39993 (11)0.0235 (4)
H150.83420.10280.40280.028*
C160.75863 (12)0.3211 (2)0.38120 (11)0.0208 (4)
H160.70150.26300.37090.025*
C171.01082 (13)0.2041 (3)0.42895 (11)0.0243 (4)
H17A1.00660.14150.47810.029*
H17B1.06370.28540.43430.029*
C181.03067 (14)0.0730 (3)0.36592 (13)0.0296 (4)
H180.97990.01510.36410.035*
C191.03265 (17)0.1601 (4)0.28777 (13)0.0417 (6)
H19A1.04520.07320.24870.062*
H19B1.08140.24840.28870.062*
H19C0.97260.21480.27570.062*
C201.12220 (16)0.0202 (3)0.38469 (16)0.0405 (6)
H20A1.11960.07580.43500.061*
H20B1.17310.06380.38550.061*
H20C1.13260.10830.34560.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03823 (13)0.02806 (12)0.04182 (15)0.01474 (8)0.01190 (10)0.01239 (9)
S10.0297 (2)0.0211 (2)0.0206 (2)0.00849 (18)0.00986 (18)0.00110 (17)
O10.0333 (7)0.0177 (7)0.0350 (8)0.0082 (5)0.0176 (6)0.0041 (6)
N10.0219 (7)0.0166 (7)0.0181 (7)0.0020 (6)0.0074 (6)0.0005 (6)
N20.0195 (7)0.0136 (7)0.0195 (7)0.0024 (5)0.0054 (6)0.0008 (6)
C10.0181 (8)0.0158 (8)0.0185 (8)0.0034 (6)0.0007 (7)0.0001 (7)
C20.0198 (8)0.0189 (8)0.0205 (9)0.0013 (6)0.0039 (7)0.0009 (7)
C30.0218 (8)0.0186 (8)0.0274 (10)0.0023 (7)0.0012 (7)0.0018 (7)
C40.0308 (10)0.0220 (9)0.0209 (9)0.0034 (8)0.0018 (8)0.0053 (7)
C50.0283 (9)0.0248 (9)0.0187 (9)0.0044 (7)0.0060 (7)0.0002 (7)
C60.0214 (8)0.0182 (8)0.0219 (9)0.0010 (7)0.0057 (7)0.0019 (7)
C70.0161 (7)0.0178 (8)0.0173 (8)0.0001 (6)0.0013 (6)0.0014 (6)
C80.0191 (8)0.0175 (8)0.0205 (9)0.0006 (6)0.0043 (7)0.0002 (7)
C90.0184 (8)0.0166 (8)0.0193 (9)0.0022 (6)0.0048 (7)0.0012 (7)
C100.0228 (9)0.0253 (9)0.0197 (9)0.0003 (7)0.0032 (7)0.0015 (7)
C110.0210 (8)0.0186 (8)0.0147 (8)0.0005 (6)0.0056 (6)0.0006 (6)
C120.0248 (9)0.0169 (8)0.0217 (9)0.0028 (7)0.0017 (7)0.0007 (7)
C130.0223 (9)0.0234 (9)0.0212 (9)0.0048 (7)0.0008 (7)0.0012 (7)
C140.0226 (8)0.0236 (9)0.0161 (8)0.0011 (7)0.0051 (7)0.0002 (7)
C150.0255 (9)0.0179 (8)0.0277 (10)0.0016 (7)0.0073 (7)0.0014 (7)
C160.0195 (8)0.0184 (9)0.0249 (9)0.0033 (6)0.0059 (7)0.0005 (7)
C170.0220 (9)0.0266 (9)0.0246 (10)0.0020 (7)0.0033 (7)0.0029 (8)
C180.0233 (9)0.0289 (10)0.0369 (12)0.0032 (8)0.0060 (8)0.0029 (9)
C190.0402 (13)0.0554 (15)0.0300 (12)0.0115 (11)0.0090 (10)0.0025 (11)
C200.0315 (11)0.0401 (13)0.0508 (15)0.0122 (9)0.0115 (10)0.0026 (11)
Geometric parameters (Å, º) top
Br1—C31.8930 (19)C10—H10C0.9800
S1—C71.6699 (18)C11—C161.392 (2)
O1—C81.225 (2)C11—C121.392 (3)
N1—C71.335 (2)C12—C131.390 (3)
N1—C11.415 (2)C12—H120.9500
N1—H10.8800C13—C141.388 (3)
N2—C81.378 (2)C13—H130.9500
N2—C71.390 (2)C14—C151.396 (3)
N2—H2A0.8800C14—C171.511 (3)
C1—C61.391 (2)C15—C161.391 (3)
C1—C21.397 (2)C15—H150.9500
C2—C31.375 (3)C16—H160.9500
C2—H20.9500C17—C181.532 (3)
C3—C41.385 (3)C17—H17A0.9900
C4—C51.387 (3)C17—H17B0.9900
C4—H40.9500C18—C191.523 (3)
C5—C61.389 (3)C18—C201.529 (3)
C5—H50.9500C18—H181.0000
C6—H60.9500C19—H19A0.9800
C8—C91.514 (2)C19—H19B0.9800
C9—C111.523 (2)C19—H19C0.9800
C9—C101.531 (3)C20—H20A0.9800
C9—H91.0000C20—H20B0.9800
C10—H10A0.9800C20—H20C0.9800
C10—H10B0.9800
C7—N1—C1132.37 (16)C16—C11—C12118.52 (17)
C7—N1—H1113.8C16—C11—C9120.56 (16)
C1—N1—H1113.8C12—C11—C9120.72 (16)
C8—N2—C7128.34 (15)C13—C12—C11120.65 (17)
C8—N2—H2A115.8C13—C12—H12119.7
C7—N2—H2A115.8C11—C12—H12119.7
C6—C1—C2119.89 (17)C14—C13—C12121.03 (17)
C6—C1—N1126.14 (16)C14—C13—H13119.5
C2—C1—N1113.97 (15)C12—C13—H13119.5
C3—C2—C1119.69 (17)C13—C14—C15118.23 (17)
C3—C2—H2120.2C13—C14—C17120.57 (17)
C1—C2—H2120.2C15—C14—C17121.15 (17)
C2—C3—C4121.70 (17)C16—C15—C14120.82 (17)
C2—C3—Br1118.02 (14)C16—C15—H15119.6
C4—C3—Br1120.27 (14)C14—C15—H15119.6
C3—C4—C5117.87 (17)C15—C16—C11120.67 (17)
C3—C4—H4121.1C15—C16—H16119.7
C5—C4—H4121.1C11—C16—H16119.7
C4—C5—C6121.99 (17)C14—C17—C18114.29 (16)
C4—C5—H5119.0C14—C17—H17A108.7
C6—C5—H5119.0C18—C17—H17A108.7
C5—C6—C1118.81 (17)C14—C17—H17B108.7
C5—C6—H6120.6C18—C17—H17B108.7
C1—C6—H6120.6H17A—C17—H17B107.6
N1—C7—N2114.32 (15)C19—C18—C20110.58 (18)
N1—C7—S1127.61 (14)C19—C18—C17111.29 (18)
N2—C7—S1118.07 (13)C20—C18—C17110.09 (19)
O1—C8—N2122.57 (17)C19—C18—H18108.3
O1—C8—C9122.05 (16)C20—C18—H18108.3
N2—C8—C9115.34 (15)C17—C18—H18108.3
C8—C9—C11109.53 (15)C18—C19—H19A109.5
C8—C9—C10110.35 (15)C18—C19—H19B109.5
C11—C9—C10110.31 (14)H19A—C19—H19B109.5
C8—C9—H9108.9C18—C19—H19C109.5
C11—C9—H9108.9H19A—C19—H19C109.5
C10—C9—H9108.9H19B—C19—H19C109.5
C9—C10—H10A109.5C18—C20—H20A109.5
C9—C10—H10B109.5C18—C20—H20B109.5
H10A—C10—H10B109.5H20A—C20—H20B109.5
C9—C10—H10C109.5C18—C20—H20C109.5
H10A—C10—H10C109.5H20A—C20—H20C109.5
H10B—C10—H10C109.5H20B—C20—H20C109.5
C7—N1—C1—C610.5 (3)O1—C8—C9—C1032.1 (2)
C7—N1—C1—C2169.22 (18)N2—C8—C9—C10149.93 (15)
C6—C1—C2—C32.4 (3)C8—C9—C11—C16128.02 (18)
N1—C1—C2—C3177.32 (16)C10—C9—C11—C16110.33 (19)
C1—C2—C3—C40.7 (3)C8—C9—C11—C1257.2 (2)
C1—C2—C3—Br1178.42 (13)C10—C9—C11—C1264.5 (2)
C2—C3—C4—C51.2 (3)C16—C11—C12—C132.5 (3)
Br1—C3—C4—C5179.70 (14)C9—C11—C12—C13172.45 (17)
C3—C4—C5—C61.4 (3)C11—C12—C13—C140.7 (3)
C4—C5—C6—C10.2 (3)C12—C13—C14—C151.7 (3)
C2—C1—C6—C52.2 (3)C12—C13—C14—C17175.88 (17)
N1—C1—C6—C5177.52 (17)C13—C14—C15—C162.4 (3)
C1—N1—C7—N2173.57 (17)C17—C14—C15—C16175.19 (17)
C1—N1—C7—S16.1 (3)C14—C15—C16—C110.6 (3)
C8—N2—C7—N10.1 (3)C12—C11—C16—C151.8 (3)
C8—N2—C7—S1179.81 (14)C9—C11—C16—C15173.13 (16)
C7—N2—C8—O13.6 (3)C13—C14—C17—C18123.2 (2)
C7—N2—C8—C9174.33 (16)C15—C14—C17—C1854.3 (2)
O1—C8—C9—C1189.5 (2)C14—C17—C18—C1955.3 (2)
N2—C8—C9—C1188.44 (18)C14—C17—C18—C20178.24 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.881.852.605 (2)143
N2—H2A···S1i0.882.563.4209 (15)168
Symmetry code: (i) x+1, y+1, z+1.
 

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