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In the title compound, C16H16N2OS, the benzoyl and di­methyl­phenyl substituents have trans and cis configurations, respectively, with respect to the thio­urea S atom. The aromatic rings of the two substituents are nearly perpendicular to each other. The mol­ecules are interconnected into molecular chains along the b direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008450/cv6112sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008450/cv6112Isup2.hkl
Contains datablock I

CCDC reference: 189387

Key indicators

  • Single-crystal X-ray study
  • T = 213 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.053
  • wR factor = 0.148
  • Data-to-parameter ratio = 16.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(2) - H(2A) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

N-benzoyl-N'-(2,6-dimethylphenyl)thiourea top
Crystal data top
C16H16N2OSF(000) = 600
Mr = 284.37Dx = 1.286 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.5077 (3) ÅCell parameters from 5482 reflections
b = 11.1226 (4) Åθ = 2.8–28.3°
c = 14.0147 (5) ŵ = 0.22 mm1
β = 97.823 (1)°T = 213 K
V = 1468.27 (9) Å3Slab, colorless
Z = 40.40 × 0.28 × 0.12 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3564 independent reflections
Radiation source: fine-focus sealed tube2416 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.8°
ω scansh = 1112
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.918, Tmax = 0.974l = 1812
8741 measured reflections
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 0.94 w = 1/[σ2(Fo2) + (0.0672P)2]
where P = (Fo2 + 2Fc2)/3
3564 reflections(Δ/σ)max = 0.001
219 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.52 e Å3
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
S10.53550 (6)0.41236 (5)0.61939 (4)0.03153 (18)
O10.79071 (17)0.26662 (15)0.39239 (12)0.0408 (4)
N10.58617 (18)0.23315 (16)0.50274 (13)0.0267 (4)
N20.72130 (18)0.40448 (17)0.49622 (13)0.0266 (4)
C10.8636 (2)0.5862 (2)0.39470 (17)0.0347 (5)
C20.9492 (3)0.6680 (3)0.35361 (19)0.0432 (6)
C31.0561 (2)0.6275 (3)0.30486 (19)0.0457 (7)
C41.0780 (3)0.5047 (3)0.29584 (19)0.0465 (7)
C50.9943 (2)0.4221 (2)0.33629 (17)0.0372 (5)
C60.8857 (2)0.4633 (2)0.38622 (14)0.0271 (4)
C70.7966 (2)0.3688 (2)0.42417 (14)0.0260 (4)
C80.6153 (2)0.34353 (18)0.53638 (14)0.0236 (4)
C90.4653 (2)0.16526 (18)0.52329 (14)0.0255 (4)
C100.3468 (2)0.1639 (2)0.45239 (16)0.0311 (5)
C110.2304 (3)0.0965 (2)0.47058 (19)0.0390 (6)
C120.2336 (3)0.0310 (2)0.55480 (19)0.0424 (6)
H12A0.15520.01470.56530.051*
C130.3525 (3)0.0333 (2)0.62316 (18)0.0371 (5)
C140.4718 (2)0.10102 (19)0.60898 (15)0.0298 (5)
C150.6005 (2)0.1039 (2)0.68421 (17)0.0390 (5)
H15A0.68470.10630.65330.058*
H15B0.60210.03320.72360.058*
H15C0.59710.17410.72370.058*
C160.3467 (3)0.2320 (2)0.35928 (18)0.0434 (6)
H16A0.25610.22290.32040.065*
H16B0.41980.20080.32520.065*
H16C0.36420.31570.37300.065*
H1A0.635 (2)0.209 (2)0.4628 (16)0.026 (6)*
H10.788 (3)0.628 (2)0.4272 (18)0.048 (7)*
H31.116 (3)0.695 (2)0.2757 (18)0.047 (7)*
H110.152 (3)0.101 (2)0.425 (2)0.046 (7)*
H2A0.738 (3)0.469 (2)0.5161 (19)0.037 (7)*
H130.360 (2)0.016 (2)0.682 (2)0.047 (7)*
H20.932 (3)0.753 (3)0.3671 (19)0.056 (8)*
H41.151 (3)0.473 (2)0.263 (2)0.050 (8)*
H51.003 (3)0.329 (3)0.3311 (19)0.054 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0373 (3)0.0318 (3)0.0295 (3)0.0009 (2)0.0188 (2)0.0043 (2)
O10.0487 (10)0.0349 (9)0.0449 (10)0.0076 (7)0.0287 (8)0.0108 (7)
N10.0312 (9)0.0264 (9)0.0260 (9)0.0037 (7)0.0168 (7)0.0037 (7)
N20.0308 (9)0.0240 (10)0.0274 (9)0.0050 (7)0.0130 (7)0.0044 (7)
C10.0268 (11)0.0408 (14)0.0377 (13)0.0005 (10)0.0090 (9)0.0094 (10)
C20.0348 (12)0.0418 (15)0.0527 (16)0.0022 (11)0.0053 (11)0.0194 (12)
C30.0305 (12)0.0617 (18)0.0451 (15)0.0104 (12)0.0065 (10)0.0221 (13)
C40.0351 (13)0.068 (2)0.0404 (14)0.0121 (12)0.0194 (11)0.0013 (13)
C50.0355 (12)0.0466 (15)0.0329 (12)0.0093 (10)0.0171 (10)0.0086 (10)
C60.0237 (9)0.0369 (12)0.0212 (10)0.0045 (9)0.0050 (7)0.0010 (8)
C70.0247 (10)0.0325 (12)0.0223 (10)0.0006 (9)0.0088 (7)0.0014 (8)
C80.0250 (9)0.0258 (11)0.0210 (10)0.0007 (8)0.0072 (7)0.0010 (7)
C90.0300 (10)0.0223 (10)0.0272 (11)0.0026 (8)0.0143 (8)0.0029 (8)
C100.0354 (11)0.0286 (12)0.0311 (11)0.0014 (9)0.0106 (9)0.0031 (8)
C110.0335 (12)0.0397 (14)0.0441 (14)0.0038 (10)0.0069 (10)0.0033 (11)
C120.0379 (13)0.0406 (15)0.0535 (16)0.0095 (11)0.0236 (11)0.0028 (11)
C130.0449 (13)0.0351 (13)0.0360 (13)0.0031 (10)0.0227 (11)0.0040 (10)
C140.0354 (11)0.0274 (11)0.0296 (11)0.0002 (9)0.0148 (9)0.0010 (8)
C150.0446 (13)0.0443 (14)0.0297 (12)0.0010 (11)0.0109 (10)0.0059 (10)
C160.0499 (14)0.0433 (15)0.0359 (13)0.0046 (12)0.0022 (11)0.0058 (11)
Geometric parameters (Å, º) top
S1—C81.6599 (19)C6—C71.494 (3)
O1—C71.219 (3)C9—C141.392 (3)
N1—C81.331 (3)C9—C101.397 (3)
N1—C91.436 (2)C10—C111.389 (3)
N1—H1A0.82 (2)C10—C161.509 (3)
N2—C71.373 (2)C11—C121.384 (4)
N2—C81.395 (2)C11—H110.92 (3)
N2—H2A0.78 (3)C12—C131.379 (3)
C1—C61.390 (3)C12—H12A0.9300
C1—C21.396 (3)C13—C141.398 (3)
C1—H11.01 (3)C13—H130.98 (3)
C2—C31.375 (4)C14—C151.503 (3)
C2—H20.98 (3)C15—H15A0.9600
C3—C41.390 (4)C15—H15B0.9600
C3—H31.06 (3)C15—H15C0.9600
C4—C51.386 (3)C16—H16A0.9600
C4—H40.95 (3)C16—H16B0.9600
C5—C61.401 (3)C16—H16C0.9600
C5—H51.05 (3)
C8—N1—C9123.20 (17)C14—C9—C10123.00 (19)
C8—N1—H1A115.5 (16)C14—C9—N1120.03 (19)
C9—N1—H1A120.7 (16)C10—C9—N1116.92 (18)
C7—N2—C8129.31 (19)C11—C10—C9117.4 (2)
C7—N2—H2A115.4 (19)C11—C10—C16121.6 (2)
C8—N2—H2A115.2 (19)C9—C10—C16120.99 (19)
C6—C1—C2120.1 (2)C12—C11—C10121.0 (2)
C6—C1—H1127.9 (15)C12—C11—H11123.3 (16)
C2—C1—H1112.0 (15)C10—C11—H11115.6 (16)
C3—C2—C1120.2 (3)C13—C12—C11120.2 (2)
C3—C2—H2124.3 (16)C13—C12—H12A119.9
C1—C2—H2115.3 (17)C11—C12—H12A119.9
C2—C3—C4119.8 (2)C12—C13—C14121.1 (2)
C2—C3—H3115.7 (15)C12—C13—H13121.9 (14)
C4—C3—H3124.4 (15)C14—C13—H13116.9 (14)
C5—C4—C3120.8 (2)C9—C14—C13117.2 (2)
C5—C4—H4116.8 (17)C9—C14—C15122.03 (19)
C3—C4—H4122.4 (17)C13—C14—C15120.7 (2)
C4—C5—C6119.4 (2)C14—C15—H15A109.5
C4—C5—H5125.1 (14)C14—C15—H15B109.5
C6—C5—H5115.4 (14)H15A—C15—H15B109.5
C1—C6—C5119.6 (2)C14—C15—H15C109.5
C1—C6—C7124.19 (18)H15A—C15—H15C109.5
C5—C6—C7116.1 (2)H15B—C15—H15C109.5
O1—C7—N2122.39 (19)C10—C16—H16A109.5
O1—C7—C6121.75 (18)C10—C16—H16B109.5
N2—C7—C6115.85 (19)H16A—C16—H16B109.5
N1—C8—N2115.61 (17)C10—C16—H16C109.5
N1—C8—S1125.52 (15)H16A—C16—H16C109.5
N2—C8—S1118.87 (15)H16B—C16—H16C109.5
C6—C1—C2—C30.2 (3)C7—N2—C8—S1176.58 (17)
C1—C2—C3—C40.6 (4)C8—N1—C9—C1483.0 (3)
C2—C3—C4—C50.7 (4)C8—N1—C9—C1099.5 (2)
C3—C4—C5—C60.5 (4)C14—C9—C10—C111.2 (3)
C2—C1—C6—C50.0 (3)N1—C9—C10—C11178.65 (19)
C2—C1—C6—C7177.5 (2)C14—C9—C10—C16178.0 (2)
C4—C5—C6—C10.1 (3)N1—C9—C10—C160.6 (3)
C4—C5—C6—C7177.6 (2)C9—C10—C11—C121.5 (3)
C8—N2—C7—O19.5 (3)C16—C10—C11—C12177.7 (2)
C8—N2—C7—C6170.05 (19)C10—C11—C12—C131.1 (4)
C1—C6—C7—O1158.0 (2)C11—C12—C13—C140.2 (4)
C5—C6—C7—O119.6 (3)C10—C9—C14—C130.4 (3)
C1—C6—C7—N221.6 (3)N1—C9—C14—C13177.77 (18)
C5—C6—C7—N2160.81 (19)C10—C9—C14—C15180.0 (2)
C9—N1—C8—N2169.15 (18)N1—C9—C14—C152.6 (3)
C9—N1—C8—S110.1 (3)C12—C13—C14—C90.1 (3)
C7—N2—C8—N12.8 (3)C12—C13—C14—C15179.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.82 (2)1.99 (2)2.670 (2)140 (2)
C13—H13···S1i0.98 (3)2.94 (3)3.862 (2)157 (2)
Symmetry code: (i) x+1, y1/2, z+3/2.
 

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