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The title compound, C16H21N3O2S, is a thio­urea derivative with cinnamoyl and 2-morpholinoethyl groups attached at the terminal two N atoms. The groups lie trans and cis, respectively, to the S atom across the thio­urea C—N bonds and the morpholine group adopts a chair conformation. The mol­ecules are linked by N—H...O hydrogen bonds, forming an infinite one-dimensional chain along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030831/rn6031sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030831/rn6031Isup2.hkl
Contains datablock I

CCDC reference: 259864

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.053
  • wR factor = 0.131
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 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).

1-(2-Morpholinoethyl)-3-(3-phenylacryloyl)thiourea top
Crystal data top
C16H21N3O2SF(000) = 340
Mr = 319.42Dx = 1.270 Mg m3
Triclinic, P1Melting point = 450.5–453 K
a = 6.1452 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.731 (2) ÅCell parameters from 775 reflections
c = 14.690 (3) Åθ = 1.4–26.0°
α = 98.711 (4)°µ = 0.20 mm1
β = 93.971 (4)°T = 273 K
γ = 104.444 (4)°Block, colourless
V = 835.6 (3) Å30.41 × 0.34 × 0.20 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3267 independent reflections
Radiation source: fine-focus sealed tube2748 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 83.66 pixels mm-1θmax = 26.0°, θmin = 1.4°
ω scansh = 77
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1212
Tmin = 0.921, Tmax = 0.960l = 1818
8635 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) = 0.131H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0564P)2 + 0.1504P]
where P = (Fo2 + 2Fc2)/3
3267 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.15 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S11.35549 (10)1.27527 (6)0.61140 (4)0.0698 (2)
O10.8294 (3)0.98484 (15)0.74904 (12)0.0746 (5)
O21.0481 (3)0.52357 (16)0.76382 (12)0.0729 (4)
N11.0153 (3)1.19653 (17)0.70893 (12)0.0567 (4)
H1A1.02131.28680.71610.068*
N21.1533 (3)1.01339 (18)0.63855 (12)0.0611 (5)
H2A1.05180.95850.66390.073*
N31.1277 (3)0.72743 (16)0.64278 (11)0.0529 (4)
C10.3781 (4)1.3261 (3)0.90010 (16)0.0727 (6)
H10.44521.37480.85520.087*
C20.2427 (5)1.3862 (3)0.95621 (19)0.0870 (8)
H20.21791.47420.94810.104*
C30.1453 (4)1.3182 (3)1.02322 (18)0.0830 (7)
H30.05641.36031.06140.100*
C40.1780 (5)1.1890 (3)1.0342 (2)0.0911 (8)
H40.11321.14261.08040.109*
C50.3078 (4)1.1263 (3)0.97658 (19)0.0830 (7)
H50.32371.03550.98280.100*
C60.4148 (3)1.1952 (2)0.90991 (14)0.0581 (5)
C70.5619 (4)1.1298 (2)0.85385 (14)0.0600 (5)
H70.54141.03120.85080.072*
C80.7194 (4)1.1943 (2)0.80725 (14)0.0592 (5)
H80.74551.29280.80810.071*
C90.8556 (3)1.1142 (2)0.75376 (14)0.0562 (5)
C101.1680 (3)1.1521 (2)0.65354 (13)0.0530 (5)
C111.2957 (4)0.9461 (2)0.58235 (16)0.0660 (6)
H11A1.44410.96350.61610.079*
H11B1.31370.98620.52590.079*
C121.1847 (4)0.7870 (2)0.55938 (15)0.0671 (6)
H12A1.04810.76990.51730.081*
H12B1.28600.73830.52830.081*
C131.3131 (4)0.6869 (2)0.68884 (18)0.0690 (6)
H13A1.44580.76840.70140.083*
H13B1.35000.60910.64870.083*
C141.2488 (4)0.6393 (3)0.77800 (19)0.0784 (7)
H14A1.37170.60890.80670.094*
H14B1.22560.72010.82000.094*
C150.8693 (4)0.5653 (3)0.71794 (17)0.0700 (6)
H15A0.83820.64630.75700.084*
H15B0.73340.48610.70780.084*
C160.9283 (4)0.6063 (2)0.62717 (16)0.0677 (6)
H16A0.95740.52530.58740.081*
H16B0.80300.63240.59670.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0620 (4)0.0649 (4)0.0851 (4)0.0063 (3)0.0254 (3)0.0311 (3)
O10.0815 (11)0.0507 (9)0.0967 (12)0.0129 (7)0.0462 (9)0.0203 (8)
O20.0630 (9)0.0612 (9)0.0991 (12)0.0118 (7)0.0183 (8)0.0314 (8)
N10.0552 (10)0.0489 (9)0.0691 (10)0.0108 (7)0.0188 (8)0.0195 (8)
N20.0609 (10)0.0552 (10)0.0725 (11)0.0123 (8)0.0301 (9)0.0228 (8)
N30.0516 (9)0.0496 (9)0.0583 (10)0.0128 (7)0.0163 (7)0.0084 (7)
C10.0829 (16)0.0787 (16)0.0681 (14)0.0318 (13)0.0245 (12)0.0239 (12)
C20.104 (2)0.0899 (18)0.0855 (18)0.0505 (16)0.0271 (16)0.0224 (14)
C30.0779 (16)0.106 (2)0.0757 (16)0.0403 (15)0.0257 (13)0.0130 (15)
C40.0913 (19)0.107 (2)0.0916 (19)0.0344 (17)0.0465 (16)0.0371 (16)
C50.0866 (18)0.0793 (16)0.0981 (19)0.0296 (14)0.0436 (15)0.0340 (14)
C60.0530 (11)0.0637 (13)0.0580 (12)0.0133 (9)0.0103 (9)0.0135 (10)
C70.0634 (13)0.0561 (12)0.0633 (13)0.0154 (10)0.0179 (10)0.0153 (10)
C80.0610 (12)0.0520 (11)0.0665 (13)0.0130 (9)0.0158 (10)0.0160 (10)
C90.0545 (12)0.0534 (12)0.0608 (12)0.0085 (9)0.0143 (9)0.0161 (9)
C100.0473 (10)0.0579 (12)0.0556 (11)0.0105 (9)0.0089 (9)0.0201 (9)
C110.0665 (13)0.0679 (14)0.0706 (14)0.0186 (11)0.0314 (11)0.0218 (11)
C120.0718 (14)0.0693 (14)0.0602 (13)0.0171 (11)0.0229 (11)0.0070 (10)
C130.0498 (12)0.0608 (13)0.0994 (17)0.0120 (10)0.0190 (11)0.0226 (12)
C140.0597 (14)0.0780 (16)0.0984 (18)0.0080 (12)0.0022 (12)0.0384 (14)
C150.0518 (12)0.0688 (14)0.0861 (16)0.0042 (10)0.0165 (11)0.0188 (12)
C160.0579 (13)0.0655 (13)0.0709 (14)0.0037 (10)0.0083 (11)0.0053 (11)
Geometric parameters (Å, º) top
S1—C101.6675 (19)C5—C61.382 (3)
O1—C91.219 (2)C5—H50.9300
O2—C151.425 (3)C6—C71.459 (3)
O2—C141.426 (3)C7—C81.311 (3)
N1—C91.377 (2)C7—H70.9300
N1—C101.389 (3)C8—C91.468 (3)
N1—H1A0.8600C8—H80.9300
N2—C101.314 (3)C11—C121.503 (3)
N2—C111.449 (3)C11—H11A0.9700
N2—H2A0.8600C11—H11B0.9700
N3—C161.450 (3)C12—H12A0.9700
N3—C131.453 (3)C12—H12B0.9700
N3—C121.460 (3)C13—C141.500 (3)
C1—C61.375 (3)C13—H13A0.9700
C1—C21.380 (3)C13—H13B0.9700
C1—H10.9300C14—H14A0.9700
C2—C31.359 (3)C14—H14B0.9700
C2—H20.9300C15—C161.492 (3)
C3—C41.352 (4)C15—H15A0.9700
C3—H30.9300C15—H15B0.9700
C4—C51.380 (3)C16—H16A0.9700
C4—H40.9300C16—H16B0.9700
C15—O2—C14109.53 (16)N2—C10—S1124.57 (15)
C9—N1—C10128.18 (17)N1—C10—S1119.00 (15)
C9—N1—H1A115.9N2—C11—C12108.07 (17)
C10—N1—H1A115.9N2—C11—H11A110.1
C10—N2—C11124.72 (17)C12—C11—H11A110.1
C10—N2—H2A117.6N2—C11—H11B110.1
C11—N2—H2A117.6C12—C11—H11B110.1
C16—N3—C13109.11 (17)H11A—C11—H11B108.4
C16—N3—C12113.62 (17)N3—C12—C11111.27 (17)
C13—N3—C12113.36 (17)N3—C12—H12A109.4
C6—C1—C2120.7 (2)C11—C12—H12A109.4
C6—C1—H1119.6N3—C12—H12B109.4
C2—C1—H1119.6C11—C12—H12B109.4
C3—C2—C1120.7 (2)H12A—C12—H12B108.0
C3—C2—H2119.6N3—C13—C14110.20 (18)
C1—C2—H2119.6N3—C13—H13A109.6
C4—C3—C2119.7 (2)C14—C13—H13A109.6
C4—C3—H3120.1N3—C13—H13B109.6
C2—C3—H3120.1C14—C13—H13B109.6
C3—C4—C5119.9 (2)H13A—C13—H13B108.1
C3—C4—H4120.1O2—C14—C13111.9 (2)
C5—C4—H4120.1O2—C14—H14A109.2
C4—C5—C6121.6 (2)C13—C14—H14A109.2
C4—C5—H5119.2O2—C14—H14B109.2
C6—C5—H5119.2C13—C14—H14B109.2
C1—C6—C5117.3 (2)H14A—C14—H14B107.9
C1—C6—C7122.47 (19)O2—C15—C16111.33 (18)
C5—C6—C7120.3 (2)O2—C15—H15A109.4
C8—C7—C6127.4 (2)C16—C15—H15A109.4
C8—C7—H7116.3O2—C15—H15B109.4
C6—C7—H7116.3C16—C15—H15B109.4
C7—C8—C9121.38 (19)H15A—C15—H15B108.0
C7—C8—H8119.3N3—C16—C15109.23 (18)
C9—C8—H8119.3N3—C16—H16A109.8
O1—C9—N1122.43 (19)C15—C16—H16A109.8
O1—C9—C8122.82 (18)N3—C16—H16B109.8
N1—C9—C8114.75 (18)C15—C16—H16B109.8
N2—C10—N1116.43 (17)H16A—C16—H16B108.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.861.952.642 (3)136
N2—H2A···N30.862.392.758 (2)107
C7—H7···O10.932.482.813 (3)101
N1—H1A···O2i0.862.273.114 (2)169
C15—H15B···S1ii0.972.813.731 (3)159
Symmetry codes: (i) x, y+1, z; (ii) x1, y1, z.
 

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