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The structure of the title compound, C17H20N2S, exhibits hydrogen bonding of the type N—H...S, resulting in chains of mol­ecules running along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000323/ww2076sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000323/ww2076Isup2.hkl
Contains datablock I

CCDC reference: 636836

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.100
  • Data-to-parameter ratio = 19.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C1 .. 5.43 su PLAT318_ALERT_2_C Check Hybridisation of N1 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

N,N'-bis(2-phenylethyl)thiourea top
Crystal data top
C17H20N2SDx = 1.196 Mg m3
Mr = 284.41Melting point: 356(2) K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5741 reflections
a = 9.740 (2) Åθ = 3.1–27.6°
b = 9.173 (2) ŵ = 0.20 mm1
c = 35.354 (9) ÅT = 173 K
V = 3158.7 (12) Å3Block, colourless
Z = 80.20 × 0.16 × 0.14 mm
F(000) = 1216
Data collection top
Nonius KappaCCD
diffractometer
3523 independent reflections
Radiation source: fine-focus sealed tube2385 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω and φ scansθmax = 27.6°, θmin = 3.1°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1212
Tmin = 0.962, Tmax = 0.973k = 1111
5741 measured reflectionsl = 4545
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.029P)2 + 0.81P]
where P = (Fo2 + 2Fc2)/3
3523 reflections(Δ/σ)max = 0.001
181 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.19 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.91513 (4)0.12463 (4)0.527064 (13)0.03354 (14)
N10.81209 (15)0.35394 (14)0.56322 (4)0.0351 (4)
H10.77560.44170.56330.042*
N20.78376 (15)0.35498 (15)0.49914 (4)0.0392 (4)
H20.74770.44210.50230.047*
C10.83151 (16)0.28685 (17)0.52967 (5)0.0297 (4)
C20.8486 (2)0.28798 (19)0.59928 (5)0.0418 (5)
H2A0.94610.25750.59850.050*
H2B0.79210.19960.60320.050*
C30.82761 (19)0.39074 (18)0.63231 (5)0.0373 (4)
H3A0.88790.47690.62940.045*
H3B0.73120.42490.63270.045*
C40.86031 (18)0.31423 (17)0.66892 (5)0.0331 (4)
C50.98492 (19)0.33546 (19)0.68692 (5)0.0403 (5)
H51.04840.40370.67680.048*
C61.0188 (2)0.2587 (2)0.71946 (6)0.0482 (5)
H61.10400.27630.73170.058*
C70.9292 (2)0.1576 (2)0.73396 (6)0.0485 (5)
H70.95290.10350.75590.058*
C80.8040 (2)0.1350 (2)0.71628 (6)0.0482 (5)
H80.74170.06480.72610.058*
C90.76946 (19)0.21405 (19)0.68449 (5)0.0411 (5)
H90.68220.19980.67310.049*
C100.78662 (18)0.2965 (2)0.46098 (5)0.0373 (4)
H10A0.71030.34000.44640.045*
H10B0.77070.19000.46220.045*
C110.92014 (18)0.3242 (2)0.44006 (5)0.0409 (4)
H11A0.93870.43030.43920.049*
H11B0.99680.27660.45370.049*
C120.91180 (16)0.26546 (19)0.40039 (5)0.0343 (4)
C130.95534 (18)0.1250 (2)0.39152 (5)0.0399 (4)
H130.99420.06550.41080.048*
C140.94300 (19)0.0703 (2)0.35513 (6)0.0424 (5)
H140.97420.02550.34960.051*
C150.88551 (19)0.1545 (2)0.32682 (6)0.0429 (5)
H150.87780.11760.30180.052*
C160.83952 (19)0.2928 (2)0.33537 (6)0.0431 (5)
H160.79860.35100.31620.052*
C170.85259 (19)0.34757 (19)0.37165 (5)0.0396 (4)
H170.82050.44310.37700.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0386 (2)0.0289 (2)0.0331 (3)0.00371 (19)0.0009 (2)0.00301 (19)
N10.0495 (9)0.0284 (7)0.0273 (8)0.0084 (7)0.0007 (7)0.0019 (6)
N20.0505 (9)0.0406 (8)0.0265 (8)0.0158 (7)0.0004 (7)0.0004 (7)
C10.0290 (8)0.0318 (8)0.0284 (10)0.0020 (7)0.0013 (7)0.0009 (8)
C20.0623 (13)0.0360 (10)0.0272 (10)0.0066 (9)0.0022 (9)0.0001 (8)
C30.0432 (10)0.0368 (9)0.0319 (10)0.0057 (8)0.0047 (8)0.0058 (8)
C40.0407 (9)0.0329 (9)0.0256 (9)0.0055 (8)0.0016 (8)0.0075 (8)
C50.0456 (11)0.0420 (10)0.0333 (11)0.0025 (9)0.0016 (9)0.0006 (8)
C60.0522 (11)0.0547 (12)0.0377 (12)0.0034 (10)0.0089 (10)0.0018 (10)
C70.0695 (14)0.0503 (12)0.0256 (10)0.0104 (11)0.0054 (10)0.0013 (9)
C80.0623 (13)0.0481 (11)0.0343 (11)0.0021 (10)0.0176 (10)0.0021 (9)
C90.0421 (10)0.0463 (11)0.0349 (11)0.0004 (9)0.0043 (9)0.0100 (9)
C100.0383 (10)0.0485 (10)0.0251 (10)0.0071 (9)0.0030 (8)0.0002 (8)
C110.0424 (10)0.0504 (10)0.0299 (10)0.0048 (9)0.0007 (9)0.0012 (9)
C120.0304 (9)0.0453 (10)0.0272 (10)0.0030 (8)0.0037 (8)0.0032 (8)
C130.0369 (10)0.0480 (10)0.0348 (11)0.0039 (8)0.0005 (9)0.0086 (9)
C140.0412 (11)0.0416 (10)0.0444 (12)0.0022 (8)0.0038 (9)0.0016 (9)
C150.0448 (11)0.0540 (12)0.0300 (11)0.0083 (9)0.0026 (9)0.0034 (9)
C160.0467 (11)0.0491 (11)0.0335 (11)0.0002 (9)0.0036 (9)0.0091 (9)
C170.0448 (10)0.0405 (10)0.0336 (11)0.0021 (8)0.0008 (9)0.0024 (8)
Geometric parameters (Å, º) top
S1—C11.699 (2)C8—C91.379 (3)
N1—C11.350 (2)C8—H80.9500
N1—C21.455 (2)C9—H90.9500
N1—H10.8800C10—C111.518 (2)
N2—C11.331 (2)C10—H10A0.9900
N2—C101.452 (2)C10—H10B0.9900
N2—H20.8800C11—C121.505 (2)
C2—C31.515 (2)C11—H11A0.9900
C2—H2A0.9900C11—H11B0.9900
C2—H2B0.9900C12—C171.390 (2)
C3—C41.506 (2)C12—C131.393 (2)
C3—H3A0.9900C13—C141.386 (3)
C3—H3B0.9900C13—H130.9500
C4—C51.384 (2)C14—C151.383 (3)
C4—C91.389 (2)C14—H140.9500
C5—C61.388 (2)C15—C161.379 (3)
C5—H50.9500C15—H150.9500
C6—C71.373 (3)C16—C171.383 (3)
C6—H60.9500C16—H160.9500
C7—C81.386 (3)C17—H170.9500
C7—H70.9500
C1—N1—C2123.09 (14)C7—C8—H8119.9
C1—N1—H1118.5C8—C9—C4121.02 (18)
C2—N1—H1118.5C8—C9—H9119.5
C1—N2—C10124.96 (14)C4—C9—H9119.5
C1—N2—H2117.5N2—C10—C11114.03 (15)
C10—N2—H2117.5N2—C10—H10A108.7
N2—C1—N1116.71 (14)C11—C10—H10A108.7
N2—C1—S1122.33 (13)N2—C10—H10B108.7
N1—C1—S1120.95 (13)C11—C10—H10B108.7
N1—C2—C3112.56 (14)H10A—C10—H10B107.6
N1—C2—H2A109.1C12—C11—C10110.36 (15)
C3—C2—H2A109.1C12—C11—H11A109.6
N1—C2—H2B109.1C10—C11—H11A109.6
C3—C2—H2B109.1C12—C11—H11B109.6
H2A—C2—H2B107.8C10—C11—H11B109.6
C4—C3—C2110.12 (14)H11A—C11—H11B108.1
C4—C3—H3A109.6C17—C12—C13117.59 (17)
C2—C3—H3A109.6C17—C12—C11120.63 (16)
C4—C3—H3B109.6C13—C12—C11121.68 (16)
C2—C3—H3B109.6C14—C13—C12121.17 (17)
H3A—C3—H3B108.2C14—C13—H13119.4
C5—C4—C9117.99 (17)C12—C13—H13119.4
C5—C4—C3120.99 (16)C15—C14—C13120.31 (18)
C9—C4—C3120.93 (16)C15—C14—H14119.8
C4—C5—C6121.20 (18)C13—C14—H14119.8
C4—C5—H5119.4C16—C15—C14119.14 (19)
C6—C5—H5119.4C16—C15—H15120.4
C7—C6—C5120.07 (19)C14—C15—H15120.4
C7—C6—H6120.0C15—C16—C17120.48 (18)
C5—C6—H6120.0C15—C16—H16119.8
C6—C7—C8119.46 (19)C17—C16—H16119.8
C6—C7—H7120.3C16—C17—C12121.29 (17)
C8—C7—H7120.3C16—C17—H17119.4
C9—C8—C7120.23 (18)C12—C17—H17119.4
C9—C8—H8119.9
C10—N2—C1—N1175.80 (15)C5—C4—C9—C81.9 (3)
C10—N2—C1—S15.1 (2)C3—C4—C9—C8174.57 (16)
C2—N1—C1—N2174.97 (16)C1—N2—C10—C1185.5 (2)
C2—N1—C1—S15.9 (2)N2—C10—C11—C12177.70 (14)
C1—N1—C2—C3175.13 (16)C10—C11—C12—C1783.9 (2)
N1—C2—C3—C4177.20 (15)C10—C11—C12—C1392.3 (2)
C2—C3—C4—C5100.48 (19)C17—C12—C13—C141.5 (3)
C2—C3—C4—C975.9 (2)C11—C12—C13—C14177.86 (16)
C9—C4—C5—C60.3 (3)C12—C13—C14—C150.6 (3)
C3—C4—C5—C6176.17 (16)C13—C14—C15—C160.6 (3)
C4—C5—C6—C71.3 (3)C14—C15—C16—C171.0 (3)
C5—C6—C7—C81.3 (3)C15—C16—C17—C120.1 (3)
C6—C7—C8—C90.3 (3)C13—C12—C17—C161.1 (3)
C7—C8—C9—C41.9 (3)C11—C12—C17—C16177.54 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1i0.882.813.563 (2)144
N2—H2···S1i0.882.473.293 (2)157
Symmetry code: (i) x+3/2, y+1/2, z.
 

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