organic compounds
In the title compound, C21H25N3O2S, the p-anisoyl group is inclined to the central thiourea N2CS unit by 31.939 (11)° and the piperidine ring adopts a chair conformation. The molecule is stabilized by intra- and intermolecular interactions to form polymeric chains parallel to the ac plane.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019434/sj6102sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019434/sj6102Isup2.hkl |
CCDC reference: 277790
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.068
- wR factor = 0.133
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
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, 2003).
N-(1-Benzylpiperidin-4-yl)-N'-(4-methoxybenzoyl)thiourea top
Crystal data top
C21H25N3O2S | F(000) = 816 |
Mr = 383.50 | Dx = 1.261 Mg m−3 |
Monoclinic, P21/n | Melting point = 412.3–413.1 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 11.775 (2) Å | Cell parameters from 1914 reflections |
b = 7.0646 (14) Å | θ = 1.6–25.5° |
c = 24.362 (5) Å | µ = 0.18 mm−1 |
β = 94.777 (4)° | T = 273 K |
V = 2019.6 (7) Å3 | Plate, colourless |
Z = 4 | 0.46 × 0.20 × 0.09 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3754 independent reflections |
Radiation source: fine-focus sealed tube | 2953 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.5°, θmin = 1.6° |
ω scans | h = −13→14 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −8→8 |
Tmin = 0.921, Tmax = 0.983 | l = −29→19 |
10172 measured reflections |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.18 | w = 1/[σ2(Fo2) + (0.0387P)2 + 0.7201P] where P = (Fo2 + 2Fc2)/3 |
3754 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.86351 (7) | 0.93879 (11) | 1.04903 (3) | 0.0595 (3) | |
O1 | 0.86926 (17) | 0.4333 (3) | 0.93436 (8) | 0.0633 (6) | |
O2 | 1.13780 (19) | 0.7112 (3) | 0.73538 (8) | 0.0681 (6) | |
N1 | 0.92115 (18) | 0.7255 (3) | 0.96656 (9) | 0.0463 (6) | |
H1A | 0.9678 | 0.8167 | 0.9620 | 0.056* | |
N2 | 0.79409 (18) | 0.5917 (3) | 1.02191 (9) | 0.0469 (6) | |
H2A | 0.8015 | 0.4923 | 1.0022 | 0.056* | |
N3 | 0.49409 (18) | 0.4616 (3) | 1.09935 (9) | 0.0450 (5) | |
C1 | 0.9848 (2) | 0.7980 (4) | 0.85468 (11) | 0.0516 (7) | |
H1B | 0.9538 | 0.9017 | 0.8716 | 0.062* | |
C2 | 1.0370 (2) | 0.8230 (4) | 0.80689 (12) | 0.0560 (8) | |
H2B | 1.0393 | 0.9426 | 0.7911 | 0.067* | |
C3 | 1.0861 (2) | 0.6708 (4) | 0.78207 (11) | 0.0503 (7) | |
C4 | 1.0801 (2) | 0.4929 (4) | 0.80489 (11) | 0.0522 (7) | |
H4A | 1.1130 | 0.3899 | 0.7885 | 0.063* | |
C5 | 1.0252 (2) | 0.4685 (4) | 0.85210 (11) | 0.0499 (7) | |
H5A | 1.0198 | 0.3478 | 0.8669 | 0.060* | |
C6 | 0.9779 (2) | 0.6202 (4) | 0.87791 (11) | 0.0433 (6) | |
C7 | 0.9183 (2) | 0.5831 (4) | 0.92812 (11) | 0.0456 (7) | |
C8 | 0.8576 (2) | 0.7399 (4) | 1.01205 (11) | 0.0448 (7) | |
C9 | 0.7120 (2) | 0.5832 (4) | 1.06385 (11) | 0.0450 (7) | |
H9A | 0.7453 | 0.6463 | 1.0972 | 0.054* | |
C10 | 0.6882 (2) | 0.3790 (4) | 1.07752 (12) | 0.0512 (7) | |
H10A | 0.7581 | 0.3185 | 1.0924 | 0.061* | |
H10B | 0.6607 | 0.3122 | 1.0443 | 0.061* | |
C11 | 0.6000 (2) | 0.3687 (4) | 1.11919 (12) | 0.0529 (7) | |
H11A | 0.5846 | 0.2370 | 1.1271 | 0.064* | |
H11B | 0.6301 | 0.4284 | 1.1532 | 0.064* | |
C12 | 0.5150 (2) | 0.6606 (4) | 1.08701 (12) | 0.0533 (7) | |
H12A | 0.5426 | 0.7253 | 1.1206 | 0.064* | |
H12B | 0.4439 | 0.7197 | 1.0732 | 0.064* | |
C13 | 0.6015 (2) | 0.6824 (4) | 1.04463 (12) | 0.0503 (7) | |
H13A | 0.6161 | 0.8157 | 1.0389 | 0.060* | |
H13B | 0.5710 | 0.6286 | 1.0098 | 0.060* | |
C14 | 0.4100 (2) | 0.4498 (4) | 1.14009 (12) | 0.0550 (8) | |
H14A | 0.3457 | 0.5297 | 1.1281 | 0.066* | |
H14B | 0.4437 | 0.4999 | 1.1748 | 0.066* | |
C15 | 0.3669 (2) | 0.2535 (4) | 1.14981 (12) | 0.0473 (7) | |
C16 | 0.3255 (2) | 0.1405 (4) | 1.10649 (12) | 0.0538 (7) | |
H16A | 0.3308 | 0.1820 | 1.0706 | 0.065* | |
C17 | 0.2765 (3) | −0.0320 (4) | 1.11539 (14) | 0.0630 (9) | |
H17A | 0.2475 | −0.1049 | 1.0857 | 0.076* | |
C18 | 0.2704 (3) | −0.0970 (5) | 1.16827 (16) | 0.0689 (9) | |
H18A | 0.2372 | −0.2137 | 1.1744 | 0.083* | |
C19 | 0.3132 (3) | 0.0103 (5) | 1.21168 (15) | 0.0716 (10) | |
H19A | 0.3104 | −0.0343 | 1.2475 | 0.086* | |
C20 | 0.3610 (2) | 0.1855 (5) | 1.20259 (13) | 0.0615 (8) | |
H20A | 0.3894 | 0.2583 | 1.2324 | 0.074* | |
C21 | 1.1860 (3) | 0.5599 (5) | 0.70765 (14) | 0.0880 (12) | |
H21A | 1.2195 | 0.6072 | 0.6758 | 0.132* | |
H21B | 1.1277 | 0.4696 | 0.6964 | 0.132* | |
H21C | 1.2437 | 0.4999 | 0.7319 | 0.132* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0659 (5) | 0.0493 (5) | 0.0667 (5) | −0.0159 (4) | 0.0267 (4) | −0.0141 (4) |
O1 | 0.0704 (14) | 0.0546 (13) | 0.0684 (14) | −0.0206 (11) | 0.0264 (11) | −0.0154 (10) |
O2 | 0.0854 (16) | 0.0695 (14) | 0.0526 (13) | 0.0019 (12) | 0.0255 (11) | −0.0002 (11) |
N1 | 0.0428 (13) | 0.0501 (13) | 0.0477 (13) | −0.0127 (11) | 0.0142 (10) | −0.0077 (11) |
N2 | 0.0484 (14) | 0.0452 (13) | 0.0489 (13) | −0.0098 (11) | 0.0144 (11) | −0.0074 (10) |
N3 | 0.0388 (12) | 0.0478 (13) | 0.0498 (13) | −0.0015 (10) | 0.0126 (10) | 0.0042 (11) |
C1 | 0.0492 (17) | 0.0551 (18) | 0.0516 (18) | 0.0047 (14) | 0.0104 (14) | −0.0076 (14) |
C2 | 0.0623 (19) | 0.0524 (18) | 0.0544 (18) | 0.0050 (15) | 0.0117 (15) | 0.0042 (15) |
C3 | 0.0489 (17) | 0.0605 (19) | 0.0417 (16) | −0.0026 (14) | 0.0050 (13) | −0.0037 (14) |
C4 | 0.0590 (19) | 0.0532 (18) | 0.0453 (17) | 0.0050 (14) | 0.0091 (14) | −0.0092 (14) |
C5 | 0.0532 (18) | 0.0466 (17) | 0.0499 (17) | −0.0010 (14) | 0.0037 (14) | −0.0025 (13) |
C6 | 0.0348 (15) | 0.0504 (17) | 0.0447 (16) | −0.0035 (12) | 0.0031 (12) | −0.0047 (13) |
C7 | 0.0381 (15) | 0.0488 (17) | 0.0504 (17) | −0.0034 (13) | 0.0064 (13) | −0.0052 (13) |
C8 | 0.0403 (15) | 0.0476 (16) | 0.0469 (16) | −0.0054 (13) | 0.0059 (12) | 0.0009 (13) |
C9 | 0.0421 (16) | 0.0492 (16) | 0.0447 (16) | −0.0060 (13) | 0.0094 (12) | −0.0030 (13) |
C10 | 0.0415 (16) | 0.0494 (17) | 0.0641 (19) | −0.0006 (13) | 0.0136 (14) | 0.0050 (14) |
C11 | 0.0455 (17) | 0.0546 (18) | 0.0596 (18) | −0.0015 (14) | 0.0096 (14) | 0.0130 (14) |
C12 | 0.0453 (17) | 0.0483 (17) | 0.068 (2) | 0.0012 (14) | 0.0143 (14) | 0.0054 (14) |
C13 | 0.0471 (17) | 0.0455 (16) | 0.0591 (18) | −0.0055 (13) | 0.0087 (14) | 0.0092 (14) |
C14 | 0.0488 (17) | 0.0585 (18) | 0.0602 (18) | −0.0052 (15) | 0.0188 (14) | −0.0043 (15) |
C15 | 0.0349 (15) | 0.0540 (17) | 0.0552 (18) | 0.0020 (13) | 0.0159 (13) | 0.0031 (14) |
C16 | 0.0494 (18) | 0.0561 (18) | 0.0575 (18) | 0.0022 (15) | 0.0152 (14) | 0.0058 (15) |
C17 | 0.0551 (19) | 0.055 (2) | 0.081 (2) | 0.0032 (16) | 0.0152 (17) | −0.0076 (17) |
C18 | 0.059 (2) | 0.0499 (19) | 0.102 (3) | 0.0042 (16) | 0.031 (2) | 0.0128 (19) |
C19 | 0.069 (2) | 0.078 (2) | 0.071 (2) | 0.0023 (19) | 0.0238 (19) | 0.023 (2) |
C20 | 0.0528 (19) | 0.075 (2) | 0.058 (2) | −0.0035 (16) | 0.0145 (15) | 0.0031 (17) |
C21 | 0.118 (3) | 0.090 (3) | 0.062 (2) | 0.018 (2) | 0.042 (2) | −0.004 (2) |
Geometric parameters (Å, º) top
S1—C8 | 1.667 (3) | C10—C11 | 1.514 (3) |
O1—C7 | 1.221 (3) | C10—H10A | 0.9700 |
O2—C3 | 1.364 (3) | C10—H10B | 0.9700 |
O2—C21 | 1.409 (4) | C11—H11A | 0.9700 |
N1—C7 | 1.373 (3) | C11—H11B | 0.9700 |
N1—C8 | 1.391 (3) | C12—C13 | 1.517 (4) |
N1—H1A | 0.8600 | C12—H12A | 0.9700 |
N2—C8 | 1.321 (3) | C12—H12B | 0.9700 |
N2—C9 | 1.465 (3) | C13—H13A | 0.9700 |
N2—H2A | 0.8600 | C13—H13B | 0.9700 |
N3—C11 | 1.456 (3) | C14—C15 | 1.502 (4) |
N3—C14 | 1.462 (3) | C14—H14A | 0.9700 |
N3—C12 | 1.463 (3) | C14—H14B | 0.9700 |
C1—C2 | 1.372 (4) | C15—C16 | 1.379 (4) |
C1—C6 | 1.383 (4) | C15—C20 | 1.380 (4) |
C1—H1B | 0.9300 | C16—C17 | 1.373 (4) |
C2—C3 | 1.383 (4) | C16—H16A | 0.9300 |
C2—H2B | 0.9300 | C17—C18 | 1.375 (4) |
C3—C4 | 1.379 (4) | C17—H17A | 0.9300 |
C4—C5 | 1.376 (4) | C18—C19 | 1.363 (5) |
C4—H4A | 0.9300 | C18—H18A | 0.9300 |
C5—C6 | 1.383 (4) | C19—C20 | 1.385 (4) |
C5—H5A | 0.9300 | C19—H19A | 0.9300 |
C6—C7 | 1.483 (4) | C20—H20A | 0.9300 |
C9—C10 | 1.512 (4) | C21—H21A | 0.9600 |
C9—C13 | 1.518 (4) | C21—H21B | 0.9600 |
C9—H9A | 0.9800 | C21—H21C | 0.9600 |
C3—O2—C21 | 117.8 (2) | N3—C11—H11A | 109.2 |
C7—N1—C8 | 127.8 (2) | C10—C11—H11A | 109.2 |
C7—N1—H1A | 116.1 | N3—C11—H11B | 109.2 |
C8—N1—H1A | 116.1 | C10—C11—H11B | 109.2 |
C8—N2—C9 | 125.2 (2) | H11A—C11—H11B | 107.9 |
C8—N2—H2A | 117.4 | N3—C12—C13 | 111.8 (2) |
C9—N2—H2A | 117.4 | N3—C12—H12A | 109.3 |
C11—N3—C14 | 111.0 (2) | C13—C12—H12A | 109.3 |
C11—N3—C12 | 110.3 (2) | N3—C12—H12B | 109.3 |
C14—N3—C12 | 109.3 (2) | C13—C12—H12B | 109.3 |
C2—C1—C6 | 120.6 (3) | H12A—C12—H12B | 107.9 |
C2—C1—H1B | 119.7 | C12—C13—C9 | 110.5 (2) |
C6—C1—H1B | 119.7 | C12—C13—H13A | 109.5 |
C1—C2—C3 | 120.3 (3) | C9—C13—H13A | 109.5 |
C1—C2—H2B | 119.9 | C12—C13—H13B | 109.5 |
C3—C2—H2B | 119.9 | C9—C13—H13B | 109.5 |
O2—C3—C4 | 124.6 (3) | H13A—C13—H13B | 108.1 |
O2—C3—C2 | 115.7 (3) | N3—C14—C15 | 114.6 (2) |
C4—C3—C2 | 119.7 (3) | N3—C14—H14A | 108.6 |
C5—C4—C3 | 119.6 (3) | C15—C14—H14A | 108.6 |
C5—C4—H4A | 120.2 | N3—C14—H14B | 108.6 |
C3—C4—H4A | 120.2 | C15—C14—H14B | 108.6 |
C4—C5—C6 | 121.2 (3) | H14A—C14—H14B | 107.6 |
C4—C5—H5A | 119.4 | C16—C15—C20 | 118.0 (3) |
C6—C5—H5A | 119.4 | C16—C15—C14 | 121.1 (3) |
C5—C6—C1 | 118.6 (3) | C20—C15—C14 | 120.8 (3) |
C5—C6—C7 | 118.3 (2) | C17—C16—C15 | 121.3 (3) |
C1—C6—C7 | 123.1 (2) | C17—C16—H16A | 119.4 |
O1—C7—N1 | 122.3 (3) | C15—C16—H16A | 119.4 |
O1—C7—C6 | 121.1 (2) | C16—C17—C18 | 120.0 (3) |
N1—C7—C6 | 116.5 (2) | C16—C17—H17A | 120.0 |
N2—C8—N1 | 115.9 (2) | C18—C17—H17A | 120.0 |
N2—C8—S1 | 124.6 (2) | C19—C18—C17 | 119.8 (3) |
N1—C8—S1 | 119.4 (2) | C19—C18—H18A | 120.1 |
N2—C9—C10 | 109.7 (2) | C17—C18—H18A | 120.1 |
N2—C9—C13 | 111.4 (2) | C18—C19—C20 | 120.1 (3) |
C10—C9—C13 | 109.8 (2) | C18—C19—H19A | 119.9 |
N2—C9—H9A | 108.6 | C20—C19—H19A | 119.9 |
C10—C9—H9A | 108.6 | C15—C20—C19 | 120.8 (3) |
C13—C9—H9A | 108.6 | C15—C20—H20A | 119.6 |
C9—C10—C11 | 110.1 (2) | C19—C20—H20A | 119.6 |
C9—C10—H10A | 109.6 | O2—C21—H21A | 109.5 |
C11—C10—H10A | 109.6 | O2—C21—H21B | 109.5 |
C9—C10—H10B | 109.6 | H21A—C21—H21B | 109.5 |
C11—C10—H10B | 109.6 | O2—C21—H21C | 109.5 |
H10A—C10—H10B | 108.2 | H21A—C21—H21C | 109.5 |
N3—C11—C10 | 111.9 (2) | H21B—C21—H21C | 109.5 |
C6—C1—C2—C3 | −1.7 (4) | C8—N2—C9—C13 | 78.8 (3) |
C21—O2—C3—C4 | 1.7 (4) | N2—C9—C10—C11 | −177.8 (2) |
C21—O2—C3—C2 | −178.1 (3) | C13—C9—C10—C11 | −55.0 (3) |
C1—C2—C3—O2 | −178.7 (3) | C14—N3—C11—C10 | 179.9 (2) |
C1—C2—C3—C4 | 1.5 (4) | C12—N3—C11—C10 | −58.8 (3) |
O2—C3—C4—C5 | −179.7 (3) | C9—C10—C11—N3 | 58.0 (3) |
C2—C3—C4—C5 | 0.1 (4) | C11—N3—C12—C13 | 57.9 (3) |
C3—C4—C5—C6 | −1.4 (4) | C14—N3—C12—C13 | −179.8 (2) |
C4—C5—C6—C1 | 1.3 (4) | N3—C12—C13—C9 | −56.3 (3) |
C4—C5—C6—C7 | 179.0 (2) | N2—C9—C13—C12 | 176.2 (2) |
C2—C1—C6—C5 | 0.3 (4) | C10—C9—C13—C12 | 54.5 (3) |
C2—C1—C6—C7 | −177.3 (3) | C11—N3—C14—C15 | −67.4 (3) |
C8—N1—C7—O1 | −11.3 (4) | C12—N3—C14—C15 | 170.7 (2) |
C8—N1—C7—C6 | 168.5 (2) | N3—C14—C15—C16 | −51.5 (4) |
C5—C6—C7—O1 | −30.8 (4) | N3—C14—C15—C20 | 132.7 (3) |
C1—C6—C7—O1 | 146.8 (3) | C20—C15—C16—C17 | 2.0 (4) |
C5—C6—C7—N1 | 149.4 (2) | C14—C15—C16—C17 | −174.0 (3) |
C1—C6—C7—N1 | −33.0 (4) | C15—C16—C17—C18 | −1.5 (4) |
C9—N2—C8—N1 | −173.4 (2) | C16—C17—C18—C19 | −0.1 (5) |
C9—N2—C8—S1 | 5.2 (4) | C17—C18—C19—C20 | 1.1 (5) |
C7—N1—C8—N2 | 6.1 (4) | C16—C15—C20—C19 | −1.0 (4) |
C7—N1—C8—S1 | −172.6 (2) | C14—C15—C20—C19 | 175.0 (3) |
C8—N2—C9—C10 | −159.4 (2) | C18—C19—C20—C15 | −0.5 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.94 | 2.627 (3) | 136 |
C9—H9A···S1 | 0.98 | 2.80 | 3.120 (3) | 100 |
N1—H1A···S1i | 0.86 | 2.66 | 3.516 (2) | 172 |
C21—H21C···O2ii | 0.96 | 2.56 | 3.438 (4) | 152 |
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+5/2, y−1/2, −z+3/2. |