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organic compounds
The structure of the title compound, C17H20N2S, exhibits hydrogen bonding of the type N—HS, resulting in chains of molecules running along the b axis.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000323/ww2076sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000323/ww2076Isup2.hkl |
CCDC reference: 636836
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
C17H20N2S | Dx = 1.196 Mg m−3 |
Mr = 284.41 | Melting point: 356(2) K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5741 reflections |
a = 9.740 (2) Å | θ = 3.1–27.6° |
b = 9.173 (2) Å | µ = 0.20 mm−1 |
c = 35.354 (9) Å | T = 173 K |
V = 3158.7 (12) Å3 | Block, colourless |
Z = 8 | 0.20 × 0.16 × 0.14 mm |
F(000) = 1216 |
Data collection top
Nonius KappaCCD diffractometer | 3523 independent reflections |
Radiation source: fine-focus sealed tube | 2385 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω and φ scans | θmax = 27.6°, θmin = 3.1° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −12→12 |
Tmin = 0.962, Tmax = 0.973 | k = −11→11 |
5741 measured reflections | l = −45→45 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-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 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.91513 (4) | 0.12463 (4) | 0.527064 (13) | 0.03354 (14) | |
N1 | 0.81209 (15) | 0.35394 (14) | 0.56322 (4) | 0.0351 (4) | |
H1 | 0.7756 | 0.4417 | 0.5633 | 0.042* | |
N2 | 0.78376 (15) | 0.35498 (15) | 0.49914 (4) | 0.0392 (4) | |
H2 | 0.7477 | 0.4421 | 0.5023 | 0.047* | |
C1 | 0.83151 (16) | 0.28685 (17) | 0.52967 (5) | 0.0297 (4) | |
C2 | 0.8486 (2) | 0.28798 (19) | 0.59928 (5) | 0.0418 (5) | |
H2A | 0.9461 | 0.2575 | 0.5985 | 0.050* | |
H2B | 0.7921 | 0.1996 | 0.6032 | 0.050* | |
C3 | 0.82761 (19) | 0.39074 (18) | 0.63231 (5) | 0.0373 (4) | |
H3A | 0.8879 | 0.4769 | 0.6294 | 0.045* | |
H3B | 0.7312 | 0.4249 | 0.6327 | 0.045* | |
C4 | 0.86031 (18) | 0.31423 (17) | 0.66892 (5) | 0.0331 (4) | |
C5 | 0.98492 (19) | 0.33546 (19) | 0.68692 (5) | 0.0403 (5) | |
H5 | 1.0484 | 0.4037 | 0.6768 | 0.048* | |
C6 | 1.0188 (2) | 0.2587 (2) | 0.71946 (6) | 0.0482 (5) | |
H6 | 1.1040 | 0.2763 | 0.7317 | 0.058* | |
C7 | 0.9292 (2) | 0.1576 (2) | 0.73396 (6) | 0.0485 (5) | |
H7 | 0.9529 | 0.1035 | 0.7559 | 0.058* | |
C8 | 0.8040 (2) | 0.1350 (2) | 0.71628 (6) | 0.0482 (5) | |
H8 | 0.7417 | 0.0648 | 0.7261 | 0.058* | |
C9 | 0.76946 (19) | 0.21405 (19) | 0.68449 (5) | 0.0411 (5) | |
H9 | 0.6822 | 0.1998 | 0.6731 | 0.049* | |
C10 | 0.78662 (18) | 0.2965 (2) | 0.46098 (5) | 0.0373 (4) | |
H10A | 0.7103 | 0.3400 | 0.4464 | 0.045* | |
H10B | 0.7707 | 0.1900 | 0.4622 | 0.045* | |
C11 | 0.92014 (18) | 0.3242 (2) | 0.44006 (5) | 0.0409 (4) | |
H11A | 0.9387 | 0.4303 | 0.4392 | 0.049* | |
H11B | 0.9968 | 0.2766 | 0.4537 | 0.049* | |
C12 | 0.91180 (16) | 0.26546 (19) | 0.40039 (5) | 0.0343 (4) | |
C13 | 0.95534 (18) | 0.1250 (2) | 0.39152 (5) | 0.0399 (4) | |
H13 | 0.9942 | 0.0655 | 0.4108 | 0.048* | |
C14 | 0.94300 (19) | 0.0703 (2) | 0.35513 (6) | 0.0424 (5) | |
H14 | 0.9742 | −0.0255 | 0.3496 | 0.051* | |
C15 | 0.88551 (19) | 0.1545 (2) | 0.32682 (6) | 0.0429 (5) | |
H15 | 0.8778 | 0.1176 | 0.3018 | 0.052* | |
C16 | 0.83952 (19) | 0.2928 (2) | 0.33537 (6) | 0.0431 (5) | |
H16 | 0.7986 | 0.3510 | 0.3162 | 0.052* | |
C17 | 0.85259 (19) | 0.34757 (19) | 0.37165 (5) | 0.0396 (4) | |
H17 | 0.8205 | 0.4431 | 0.3770 | 0.048* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0386 (2) | 0.0289 (2) | 0.0331 (3) | 0.00371 (19) | −0.0009 (2) | −0.00301 (19) |
N1 | 0.0495 (9) | 0.0284 (7) | 0.0273 (8) | 0.0084 (7) | −0.0007 (7) | −0.0019 (6) |
N2 | 0.0505 (9) | 0.0406 (8) | 0.0265 (8) | 0.0158 (7) | −0.0004 (7) | −0.0004 (7) |
C1 | 0.0290 (8) | 0.0318 (8) | 0.0284 (10) | −0.0020 (7) | 0.0013 (7) | −0.0009 (8) |
C2 | 0.0623 (13) | 0.0360 (10) | 0.0272 (10) | 0.0066 (9) | −0.0022 (9) | −0.0001 (8) |
C3 | 0.0432 (10) | 0.0368 (9) | 0.0319 (10) | 0.0057 (8) | −0.0047 (8) | −0.0058 (8) |
C4 | 0.0407 (9) | 0.0329 (9) | 0.0256 (9) | 0.0055 (8) | 0.0016 (8) | −0.0075 (8) |
C5 | 0.0456 (11) | 0.0420 (10) | 0.0333 (11) | −0.0025 (9) | −0.0016 (9) | 0.0006 (8) |
C6 | 0.0522 (11) | 0.0547 (12) | 0.0377 (12) | 0.0034 (10) | −0.0089 (10) | −0.0018 (10) |
C7 | 0.0695 (14) | 0.0503 (12) | 0.0256 (10) | 0.0104 (11) | 0.0054 (10) | 0.0013 (9) |
C8 | 0.0623 (13) | 0.0481 (11) | 0.0343 (11) | −0.0021 (10) | 0.0176 (10) | −0.0021 (9) |
C9 | 0.0421 (10) | 0.0463 (11) | 0.0349 (11) | 0.0004 (9) | 0.0043 (9) | −0.0100 (9) |
C10 | 0.0383 (10) | 0.0485 (10) | 0.0251 (10) | 0.0071 (9) | −0.0030 (8) | −0.0002 (8) |
C11 | 0.0424 (10) | 0.0504 (10) | 0.0299 (10) | −0.0048 (9) | 0.0007 (9) | 0.0012 (9) |
C12 | 0.0304 (9) | 0.0453 (10) | 0.0272 (10) | −0.0030 (8) | 0.0037 (8) | 0.0032 (8) |
C13 | 0.0369 (10) | 0.0480 (10) | 0.0348 (11) | 0.0039 (8) | 0.0005 (9) | 0.0086 (9) |
C14 | 0.0412 (11) | 0.0416 (10) | 0.0444 (12) | 0.0022 (8) | 0.0038 (9) | −0.0016 (9) |
C15 | 0.0448 (11) | 0.0540 (12) | 0.0300 (11) | −0.0083 (9) | 0.0026 (9) | −0.0034 (9) |
C16 | 0.0467 (11) | 0.0491 (11) | 0.0335 (11) | 0.0002 (9) | −0.0036 (9) | 0.0091 (9) |
C17 | 0.0448 (10) | 0.0405 (10) | 0.0336 (11) | 0.0021 (8) | −0.0008 (9) | 0.0024 (8) |
Geometric parameters (Å, º) top
S1—C1 | 1.699 (2) | C8—C9 | 1.379 (3) |
N1—C1 | 1.350 (2) | C8—H8 | 0.9500 |
N1—C2 | 1.455 (2) | C9—H9 | 0.9500 |
N1—H1 | 0.8800 | C10—C11 | 1.518 (2) |
N2—C1 | 1.331 (2) | C10—H10A | 0.9900 |
N2—C10 | 1.452 (2) | C10—H10B | 0.9900 |
N2—H2 | 0.8800 | C11—C12 | 1.505 (2) |
C2—C3 | 1.515 (2) | C11—H11A | 0.9900 |
C2—H2A | 0.9900 | C11—H11B | 0.9900 |
C2—H2B | 0.9900 | C12—C17 | 1.390 (2) |
C3—C4 | 1.506 (2) | C12—C13 | 1.393 (2) |
C3—H3A | 0.9900 | C13—C14 | 1.386 (3) |
C3—H3B | 0.9900 | C13—H13 | 0.9500 |
C4—C5 | 1.384 (2) | C14—C15 | 1.383 (3) |
C4—C9 | 1.389 (2) | C14—H14 | 0.9500 |
C5—C6 | 1.388 (2) | C15—C16 | 1.379 (3) |
C5—H5 | 0.9500 | C15—H15 | 0.9500 |
C6—C7 | 1.373 (3) | C16—C17 | 1.383 (3) |
C6—H6 | 0.9500 | C16—H16 | 0.9500 |
C7—C8 | 1.386 (3) | C17—H17 | 0.9500 |
C7—H7 | 0.9500 | ||
C1—N1—C2 | 123.09 (14) | C7—C8—H8 | 119.9 |
C1—N1—H1 | 118.5 | C8—C9—C4 | 121.02 (18) |
C2—N1—H1 | 118.5 | C8—C9—H9 | 119.5 |
C1—N2—C10 | 124.96 (14) | C4—C9—H9 | 119.5 |
C1—N2—H2 | 117.5 | N2—C10—C11 | 114.03 (15) |
C10—N2—H2 | 117.5 | N2—C10—H10A | 108.7 |
N2—C1—N1 | 116.71 (14) | C11—C10—H10A | 108.7 |
N2—C1—S1 | 122.33 (13) | N2—C10—H10B | 108.7 |
N1—C1—S1 | 120.95 (13) | C11—C10—H10B | 108.7 |
N1—C2—C3 | 112.56 (14) | H10A—C10—H10B | 107.6 |
N1—C2—H2A | 109.1 | C12—C11—C10 | 110.36 (15) |
C3—C2—H2A | 109.1 | C12—C11—H11A | 109.6 |
N1—C2—H2B | 109.1 | C10—C11—H11A | 109.6 |
C3—C2—H2B | 109.1 | C12—C11—H11B | 109.6 |
H2A—C2—H2B | 107.8 | C10—C11—H11B | 109.6 |
C4—C3—C2 | 110.12 (14) | H11A—C11—H11B | 108.1 |
C4—C3—H3A | 109.6 | C17—C12—C13 | 117.59 (17) |
C2—C3—H3A | 109.6 | C17—C12—C11 | 120.63 (16) |
C4—C3—H3B | 109.6 | C13—C12—C11 | 121.68 (16) |
C2—C3—H3B | 109.6 | C14—C13—C12 | 121.17 (17) |
H3A—C3—H3B | 108.2 | C14—C13—H13 | 119.4 |
C5—C4—C9 | 117.99 (17) | C12—C13—H13 | 119.4 |
C5—C4—C3 | 120.99 (16) | C15—C14—C13 | 120.31 (18) |
C9—C4—C3 | 120.93 (16) | C15—C14—H14 | 119.8 |
C4—C5—C6 | 121.20 (18) | C13—C14—H14 | 119.8 |
C4—C5—H5 | 119.4 | C16—C15—C14 | 119.14 (19) |
C6—C5—H5 | 119.4 | C16—C15—H15 | 120.4 |
C7—C6—C5 | 120.07 (19) | C14—C15—H15 | 120.4 |
C7—C6—H6 | 120.0 | C15—C16—C17 | 120.48 (18) |
C5—C6—H6 | 120.0 | C15—C16—H16 | 119.8 |
C6—C7—C8 | 119.46 (19) | C17—C16—H16 | 119.8 |
C6—C7—H7 | 120.3 | C16—C17—C12 | 121.29 (17) |
C8—C7—H7 | 120.3 | C16—C17—H17 | 119.4 |
C9—C8—C7 | 120.23 (18) | C12—C17—H17 | 119.4 |
C9—C8—H8 | 119.9 | ||
C10—N2—C1—N1 | −175.80 (15) | C5—C4—C9—C8 | −1.9 (3) |
C10—N2—C1—S1 | 5.1 (2) | C3—C4—C9—C8 | 174.57 (16) |
C2—N1—C1—N2 | 174.97 (16) | C1—N2—C10—C11 | −85.5 (2) |
C2—N1—C1—S1 | −5.9 (2) | N2—C10—C11—C12 | −177.70 (14) |
C1—N1—C2—C3 | 175.13 (16) | C10—C11—C12—C17 | 83.9 (2) |
N1—C2—C3—C4 | 177.20 (15) | C10—C11—C12—C13 | −92.3 (2) |
C2—C3—C4—C5 | 100.48 (19) | C17—C12—C13—C14 | 1.5 (3) |
C2—C3—C4—C9 | −75.9 (2) | C11—C12—C13—C14 | 177.86 (16) |
C9—C4—C5—C6 | 0.3 (3) | C12—C13—C14—C15 | −0.6 (3) |
C3—C4—C5—C6 | −176.17 (16) | C13—C14—C15—C16 | −0.6 (3) |
C4—C5—C6—C7 | 1.3 (3) | C14—C15—C16—C17 | 1.0 (3) |
C5—C6—C7—C8 | −1.3 (3) | C15—C16—C17—C12 | −0.1 (3) |
C6—C7—C8—C9 | −0.3 (3) | C13—C12—C17—C16 | −1.1 (3) |
C7—C8—C9—C4 | 1.9 (3) | C11—C12—C17—C16 | −177.54 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1i | 0.88 | 2.81 | 3.563 (2) | 144 |
N2—H2···S1i | 0.88 | 2.47 | 3.293 (2) | 157 |
Symmetry code: (i) −x+3/2, y+1/2, z. |
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