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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019434/sj6102sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019434/sj6102Isup2.hkl
Contains datablock I

CCDC reference: 277790

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](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
C21H25N3O2SF(000) = 816
Mr = 383.50Dx = 1.261 Mg m3
Monoclinic, P21/nMelting point = 412.3–413.1 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 11.775 (2) ÅCell parameters from 1914 reflections
b = 7.0646 (14) Åθ = 1.6–25.5°
c = 24.362 (5) ŵ = 0.18 mm1
β = 94.777 (4)°T = 273 K
V = 2019.6 (7) Å3Plate, colourless
Z = 40.46 × 0.20 × 0.09 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3754 independent reflections
Radiation source: fine-focus sealed tube2953 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 83.66 pixels mm-1θmax = 25.5°, θmin = 1.6°
ω scansh = 1314
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 88
Tmin = 0.921, Tmax = 0.983l = 2919
10172 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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-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 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.16 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.86351 (7)0.93879 (11)1.04903 (3)0.0595 (3)
O10.86926 (17)0.4333 (3)0.93436 (8)0.0633 (6)
O21.13780 (19)0.7112 (3)0.73538 (8)0.0681 (6)
N10.92115 (18)0.7255 (3)0.96656 (9)0.0463 (6)
H1A0.96780.81670.96200.056*
N20.79409 (18)0.5917 (3)1.02191 (9)0.0469 (6)
H2A0.80150.49231.00220.056*
N30.49409 (18)0.4616 (3)1.09935 (9)0.0450 (5)
C10.9848 (2)0.7980 (4)0.85468 (11)0.0516 (7)
H1B0.95380.90170.87160.062*
C21.0370 (2)0.8230 (4)0.80689 (12)0.0560 (8)
H2B1.03930.94260.79110.067*
C31.0861 (2)0.6708 (4)0.78207 (11)0.0503 (7)
C41.0801 (2)0.4929 (4)0.80489 (11)0.0522 (7)
H4A1.11300.38990.78850.063*
C51.0252 (2)0.4685 (4)0.85210 (11)0.0499 (7)
H5A1.01980.34780.86690.060*
C60.9779 (2)0.6202 (4)0.87791 (11)0.0433 (6)
C70.9183 (2)0.5831 (4)0.92812 (11)0.0456 (7)
C80.8576 (2)0.7399 (4)1.01205 (11)0.0448 (7)
C90.7120 (2)0.5832 (4)1.06385 (11)0.0450 (7)
H9A0.74530.64631.09720.054*
C100.6882 (2)0.3790 (4)1.07752 (12)0.0512 (7)
H10A0.75810.31851.09240.061*
H10B0.66070.31221.04430.061*
C110.6000 (2)0.3687 (4)1.11919 (12)0.0529 (7)
H11A0.58460.23701.12710.064*
H11B0.63010.42841.15320.064*
C120.5150 (2)0.6606 (4)1.08701 (12)0.0533 (7)
H12A0.54260.72531.12060.064*
H12B0.44390.71971.07320.064*
C130.6015 (2)0.6824 (4)1.04463 (12)0.0503 (7)
H13A0.61610.81571.03890.060*
H13B0.57100.62861.00980.060*
C140.4100 (2)0.4498 (4)1.14009 (12)0.0550 (8)
H14A0.34570.52971.12810.066*
H14B0.44370.49991.17480.066*
C150.3669 (2)0.2535 (4)1.14981 (12)0.0473 (7)
C160.3255 (2)0.1405 (4)1.10649 (12)0.0538 (7)
H16A0.33080.18201.07060.065*
C170.2765 (3)0.0320 (4)1.11539 (14)0.0630 (9)
H17A0.24750.10491.08570.076*
C180.2704 (3)0.0970 (5)1.16827 (16)0.0689 (9)
H18A0.23720.21371.17440.083*
C190.3132 (3)0.0103 (5)1.21168 (15)0.0716 (10)
H19A0.31040.03431.24750.086*
C200.3610 (2)0.1855 (5)1.20259 (13)0.0615 (8)
H20A0.38940.25831.23240.074*
C211.1860 (3)0.5599 (5)0.70765 (14)0.0880 (12)
H21A1.21950.60720.67580.132*
H21B1.12770.46960.69640.132*
H21C1.24370.49990.73190.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0659 (5)0.0493 (5)0.0667 (5)0.0159 (4)0.0267 (4)0.0141 (4)
O10.0704 (14)0.0546 (13)0.0684 (14)0.0206 (11)0.0264 (11)0.0154 (10)
O20.0854 (16)0.0695 (14)0.0526 (13)0.0019 (12)0.0255 (11)0.0002 (11)
N10.0428 (13)0.0501 (13)0.0477 (13)0.0127 (11)0.0142 (10)0.0077 (11)
N20.0484 (14)0.0452 (13)0.0489 (13)0.0098 (11)0.0144 (11)0.0074 (10)
N30.0388 (12)0.0478 (13)0.0498 (13)0.0015 (10)0.0126 (10)0.0042 (11)
C10.0492 (17)0.0551 (18)0.0516 (18)0.0047 (14)0.0104 (14)0.0076 (14)
C20.0623 (19)0.0524 (18)0.0544 (18)0.0050 (15)0.0117 (15)0.0042 (15)
C30.0489 (17)0.0605 (19)0.0417 (16)0.0026 (14)0.0050 (13)0.0037 (14)
C40.0590 (19)0.0532 (18)0.0453 (17)0.0050 (14)0.0091 (14)0.0092 (14)
C50.0532 (18)0.0466 (17)0.0499 (17)0.0010 (14)0.0037 (14)0.0025 (13)
C60.0348 (15)0.0504 (17)0.0447 (16)0.0035 (12)0.0031 (12)0.0047 (13)
C70.0381 (15)0.0488 (17)0.0504 (17)0.0034 (13)0.0064 (13)0.0052 (13)
C80.0403 (15)0.0476 (16)0.0469 (16)0.0054 (13)0.0059 (12)0.0009 (13)
C90.0421 (16)0.0492 (16)0.0447 (16)0.0060 (13)0.0094 (12)0.0030 (13)
C100.0415 (16)0.0494 (17)0.0641 (19)0.0006 (13)0.0136 (14)0.0050 (14)
C110.0455 (17)0.0546 (18)0.0596 (18)0.0015 (14)0.0096 (14)0.0130 (14)
C120.0453 (17)0.0483 (17)0.068 (2)0.0012 (14)0.0143 (14)0.0054 (14)
C130.0471 (17)0.0455 (16)0.0591 (18)0.0055 (13)0.0087 (14)0.0092 (14)
C140.0488 (17)0.0585 (18)0.0602 (18)0.0052 (15)0.0188 (14)0.0043 (15)
C150.0349 (15)0.0540 (17)0.0552 (18)0.0020 (13)0.0159 (13)0.0031 (14)
C160.0494 (18)0.0561 (18)0.0575 (18)0.0022 (15)0.0152 (14)0.0058 (15)
C170.0551 (19)0.055 (2)0.081 (2)0.0032 (16)0.0152 (17)0.0076 (17)
C180.059 (2)0.0499 (19)0.102 (3)0.0042 (16)0.031 (2)0.0128 (19)
C190.069 (2)0.078 (2)0.071 (2)0.0023 (19)0.0238 (19)0.023 (2)
C200.0528 (19)0.075 (2)0.058 (2)0.0035 (16)0.0145 (15)0.0031 (17)
C210.118 (3)0.090 (3)0.062 (2)0.018 (2)0.042 (2)0.004 (2)
Geometric parameters (Å, º) top
S1—C81.667 (3)C10—C111.514 (3)
O1—C71.221 (3)C10—H10A0.9700
O2—C31.364 (3)C10—H10B0.9700
O2—C211.409 (4)C11—H11A0.9700
N1—C71.373 (3)C11—H11B0.9700
N1—C81.391 (3)C12—C131.517 (4)
N1—H1A0.8600C12—H12A0.9700
N2—C81.321 (3)C12—H12B0.9700
N2—C91.465 (3)C13—H13A0.9700
N2—H2A0.8600C13—H13B0.9700
N3—C111.456 (3)C14—C151.502 (4)
N3—C141.462 (3)C14—H14A0.9700
N3—C121.463 (3)C14—H14B0.9700
C1—C21.372 (4)C15—C161.379 (4)
C1—C61.383 (4)C15—C201.380 (4)
C1—H1B0.9300C16—C171.373 (4)
C2—C31.383 (4)C16—H16A0.9300
C2—H2B0.9300C17—C181.375 (4)
C3—C41.379 (4)C17—H17A0.9300
C4—C51.376 (4)C18—C191.363 (5)
C4—H4A0.9300C18—H18A0.9300
C5—C61.383 (4)C19—C201.385 (4)
C5—H5A0.9300C19—H19A0.9300
C6—C71.483 (4)C20—H20A0.9300
C9—C101.512 (4)C21—H21A0.9600
C9—C131.518 (4)C21—H21B0.9600
C9—H9A0.9800C21—H21C0.9600
C3—O2—C21117.8 (2)N3—C11—H11A109.2
C7—N1—C8127.8 (2)C10—C11—H11A109.2
C7—N1—H1A116.1N3—C11—H11B109.2
C8—N1—H1A116.1C10—C11—H11B109.2
C8—N2—C9125.2 (2)H11A—C11—H11B107.9
C8—N2—H2A117.4N3—C12—C13111.8 (2)
C9—N2—H2A117.4N3—C12—H12A109.3
C11—N3—C14111.0 (2)C13—C12—H12A109.3
C11—N3—C12110.3 (2)N3—C12—H12B109.3
C14—N3—C12109.3 (2)C13—C12—H12B109.3
C2—C1—C6120.6 (3)H12A—C12—H12B107.9
C2—C1—H1B119.7C12—C13—C9110.5 (2)
C6—C1—H1B119.7C12—C13—H13A109.5
C1—C2—C3120.3 (3)C9—C13—H13A109.5
C1—C2—H2B119.9C12—C13—H13B109.5
C3—C2—H2B119.9C9—C13—H13B109.5
O2—C3—C4124.6 (3)H13A—C13—H13B108.1
O2—C3—C2115.7 (3)N3—C14—C15114.6 (2)
C4—C3—C2119.7 (3)N3—C14—H14A108.6
C5—C4—C3119.6 (3)C15—C14—H14A108.6
C5—C4—H4A120.2N3—C14—H14B108.6
C3—C4—H4A120.2C15—C14—H14B108.6
C4—C5—C6121.2 (3)H14A—C14—H14B107.6
C4—C5—H5A119.4C16—C15—C20118.0 (3)
C6—C5—H5A119.4C16—C15—C14121.1 (3)
C5—C6—C1118.6 (3)C20—C15—C14120.8 (3)
C5—C6—C7118.3 (2)C17—C16—C15121.3 (3)
C1—C6—C7123.1 (2)C17—C16—H16A119.4
O1—C7—N1122.3 (3)C15—C16—H16A119.4
O1—C7—C6121.1 (2)C16—C17—C18120.0 (3)
N1—C7—C6116.5 (2)C16—C17—H17A120.0
N2—C8—N1115.9 (2)C18—C17—H17A120.0
N2—C8—S1124.6 (2)C19—C18—C17119.8 (3)
N1—C8—S1119.4 (2)C19—C18—H18A120.1
N2—C9—C10109.7 (2)C17—C18—H18A120.1
N2—C9—C13111.4 (2)C18—C19—C20120.1 (3)
C10—C9—C13109.8 (2)C18—C19—H19A119.9
N2—C9—H9A108.6C20—C19—H19A119.9
C10—C9—H9A108.6C15—C20—C19120.8 (3)
C13—C9—H9A108.6C15—C20—H20A119.6
C9—C10—C11110.1 (2)C19—C20—H20A119.6
C9—C10—H10A109.6O2—C21—H21A109.5
C11—C10—H10A109.6O2—C21—H21B109.5
C9—C10—H10B109.6H21A—C21—H21B109.5
C11—C10—H10B109.6O2—C21—H21C109.5
H10A—C10—H10B108.2H21A—C21—H21C109.5
N3—C11—C10111.9 (2)H21B—C21—H21C109.5
C6—C1—C2—C31.7 (4)C8—N2—C9—C1378.8 (3)
C21—O2—C3—C41.7 (4)N2—C9—C10—C11177.8 (2)
C21—O2—C3—C2178.1 (3)C13—C9—C10—C1155.0 (3)
C1—C2—C3—O2178.7 (3)C14—N3—C11—C10179.9 (2)
C1—C2—C3—C41.5 (4)C12—N3—C11—C1058.8 (3)
O2—C3—C4—C5179.7 (3)C9—C10—C11—N358.0 (3)
C2—C3—C4—C50.1 (4)C11—N3—C12—C1357.9 (3)
C3—C4—C5—C61.4 (4)C14—N3—C12—C13179.8 (2)
C4—C5—C6—C11.3 (4)N3—C12—C13—C956.3 (3)
C4—C5—C6—C7179.0 (2)N2—C9—C13—C12176.2 (2)
C2—C1—C6—C50.3 (4)C10—C9—C13—C1254.5 (3)
C2—C1—C6—C7177.3 (3)C11—N3—C14—C1567.4 (3)
C8—N1—C7—O111.3 (4)C12—N3—C14—C15170.7 (2)
C8—N1—C7—C6168.5 (2)N3—C14—C15—C1651.5 (4)
C5—C6—C7—O130.8 (4)N3—C14—C15—C20132.7 (3)
C1—C6—C7—O1146.8 (3)C20—C15—C16—C172.0 (4)
C5—C6—C7—N1149.4 (2)C14—C15—C16—C17174.0 (3)
C1—C6—C7—N133.0 (4)C15—C16—C17—C181.5 (4)
C9—N2—C8—N1173.4 (2)C16—C17—C18—C190.1 (5)
C9—N2—C8—S15.2 (4)C17—C18—C19—C201.1 (5)
C7—N1—C8—N26.1 (4)C16—C15—C20—C191.0 (4)
C7—N1—C8—S1172.6 (2)C14—C15—C20—C19175.0 (3)
C8—N2—C9—C10159.4 (2)C18—C19—C20—C150.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.861.942.627 (3)136
C9—H9A···S10.982.803.120 (3)100
N1—H1A···S1i0.862.663.516 (2)172
C21—H21C···O2ii0.962.563.438 (4)152
Symmetry codes: (i) x+2, y+2, z+2; (ii) x+5/2, y1/2, z+3/2.
 

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