1-(2-Morpholinoethyl)-3-(3-phenyl­acryl­oyl)­thio­urea

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.

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

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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

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Computing details

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

Crystal data

C16H21N3O2S	F(000) = 340
Mr = 319.42	Dx = 1.270 Mg m^−3
Triclinic, P1	Melting point = 450.5–453 K
a = 6.1452 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.731 (2) Å	Cell parameters from 775 reflections
c = 14.690 (3) Å	θ = 1.4–26.0°
α = 98.711 (4)°	µ = 0.20 mm^−1
β = 93.971 (4)°	T = 273 K
γ = 104.444 (4)°	Block, colourless
V = 835.6 (3) Å^3	0.41 × 0.34 × 0.20 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3267 independent reflections
Radiation source: fine-focus sealed tube	2748 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 83.66 pixels mm^-1	θmax = 26.0°, θmin = 1.4°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.921, Tmax = 0.960	l = −18→18
8635 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0564P)^2 + 0.1504P] where P = (Fo^2 + 2Fc^2)/3
3267 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	1.35549 (10)	1.27527 (6)	0.61140 (4)	0.0698 (2)
O1	0.8294 (3)	0.98484 (15)	0.74904 (12)	0.0746 (5)
O2	1.0481 (3)	0.52357 (16)	0.76382 (12)	0.0729 (4)
N1	1.0153 (3)	1.19653 (17)	0.70893 (12)	0.0567 (4)
H1A	1.0213	1.2868	0.7161	0.068*
N2	1.1533 (3)	1.01339 (18)	0.63855 (12)	0.0611 (5)
H2A	1.0518	0.9585	0.6639	0.073*
N3	1.1277 (3)	0.72743 (16)	0.64278 (11)	0.0529 (4)
C1	0.3781 (4)	1.3261 (3)	0.90010 (16)	0.0727 (6)
H1	0.4452	1.3748	0.8552	0.087*
C2	0.2427 (5)	1.3862 (3)	0.95621 (19)	0.0870 (8)
H2	0.2179	1.4742	0.9481	0.104*
C3	0.1453 (4)	1.3182 (3)	1.02322 (18)	0.0830 (7)
H3	0.0564	1.3603	1.0614	0.100*
C4	0.1780 (5)	1.1890 (3)	1.0342 (2)	0.0911 (8)
H4	0.1132	1.1426	1.0804	0.109*
C5	0.3078 (4)	1.1263 (3)	0.97658 (19)	0.0830 (7)
H5	0.3237	1.0355	0.9828	0.100*
C6	0.4148 (3)	1.1952 (2)	0.90991 (14)	0.0581 (5)
C7	0.5619 (4)	1.1298 (2)	0.85385 (14)	0.0600 (5)
H7	0.5414	1.0312	0.8508	0.072*
C8	0.7194 (4)	1.1943 (2)	0.80725 (14)	0.0592 (5)
H8	0.7455	1.2928	0.8081	0.071*
C9	0.8556 (3)	1.1142 (2)	0.75376 (14)	0.0562 (5)
C10	1.1680 (3)	1.1521 (2)	0.65354 (13)	0.0530 (5)
C11	1.2957 (4)	0.9461 (2)	0.58235 (16)	0.0660 (6)
H11A	1.4441	0.9635	0.6161	0.079*
H11B	1.3137	0.9862	0.5259	0.079*
C12	1.1847 (4)	0.7870 (2)	0.55938 (15)	0.0671 (6)
H12A	1.0481	0.7699	0.5173	0.081*
H12B	1.2860	0.7383	0.5283	0.081*
C13	1.3131 (4)	0.6869 (2)	0.68884 (18)	0.0690 (6)
H13A	1.4458	0.7684	0.7014	0.083*
H13B	1.3500	0.6091	0.6487	0.083*
C14	1.2488 (4)	0.6393 (3)	0.77800 (19)	0.0784 (7)
H14A	1.3717	0.6089	0.8067	0.094*
H14B	1.2256	0.7201	0.8200	0.094*
C15	0.8693 (4)	0.5653 (3)	0.71794 (17)	0.0700 (6)
H15A	0.8382	0.6463	0.7570	0.084*
H15B	0.7334	0.4861	0.7078	0.084*
C16	0.9283 (4)	0.6063 (2)	0.62717 (16)	0.0677 (6)
H16A	0.9574	0.5253	0.5874	0.081*
H16B	0.8030	0.6324	0.5967	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0620 (4)	0.0649 (4)	0.0851 (4)	0.0063 (3)	0.0254 (3)	0.0311 (3)
O1	0.0815 (11)	0.0507 (9)	0.0967 (12)	0.0129 (7)	0.0462 (9)	0.0203 (8)
O2	0.0630 (9)	0.0612 (9)	0.0991 (12)	0.0118 (7)	0.0183 (8)	0.0314 (8)
N1	0.0552 (10)	0.0489 (9)	0.0691 (10)	0.0108 (7)	0.0188 (8)	0.0195 (8)
N2	0.0609 (10)	0.0552 (10)	0.0725 (11)	0.0123 (8)	0.0301 (9)	0.0228 (8)
N3	0.0516 (9)	0.0496 (9)	0.0583 (10)	0.0128 (7)	0.0163 (7)	0.0084 (7)
C1	0.0829 (16)	0.0787 (16)	0.0681 (14)	0.0318 (13)	0.0245 (12)	0.0239 (12)
C2	0.104 (2)	0.0899 (18)	0.0855 (18)	0.0505 (16)	0.0271 (16)	0.0224 (14)
C3	0.0779 (16)	0.106 (2)	0.0757 (16)	0.0403 (15)	0.0257 (13)	0.0130 (15)
C4	0.0913 (19)	0.107 (2)	0.0916 (19)	0.0344 (17)	0.0465 (16)	0.0371 (16)
C5	0.0866 (18)	0.0793 (16)	0.0981 (19)	0.0296 (14)	0.0436 (15)	0.0340 (14)
C6	0.0530 (11)	0.0637 (13)	0.0580 (12)	0.0133 (9)	0.0103 (9)	0.0135 (10)
C7	0.0634 (13)	0.0561 (12)	0.0633 (13)	0.0154 (10)	0.0179 (10)	0.0153 (10)
C8	0.0610 (12)	0.0520 (11)	0.0665 (13)	0.0130 (9)	0.0158 (10)	0.0160 (10)
C9	0.0545 (12)	0.0534 (12)	0.0608 (12)	0.0085 (9)	0.0143 (9)	0.0161 (9)
C10	0.0473 (10)	0.0579 (12)	0.0556 (11)	0.0105 (9)	0.0089 (9)	0.0201 (9)
C11	0.0665 (13)	0.0679 (14)	0.0706 (14)	0.0186 (11)	0.0314 (11)	0.0218 (11)
C12	0.0718 (14)	0.0693 (14)	0.0602 (13)	0.0171 (11)	0.0229 (11)	0.0070 (10)
C13	0.0498 (12)	0.0608 (13)	0.0994 (17)	0.0120 (10)	0.0190 (11)	0.0226 (12)
C14	0.0597 (14)	0.0780 (16)	0.0984 (18)	0.0080 (12)	0.0022 (12)	0.0384 (14)
C15	0.0518 (12)	0.0688 (14)	0.0861 (16)	0.0042 (10)	0.0165 (11)	0.0188 (12)
C16	0.0579 (13)	0.0655 (13)	0.0709 (14)	0.0037 (10)	0.0083 (11)	0.0053 (11)

Geometric parameters (Å, º)

S1—C10	1.6675 (19)	C5—C6	1.382 (3)
O1—C9	1.219 (2)	C5—H5	0.9300
O2—C15	1.425 (3)	C6—C7	1.459 (3)
O2—C14	1.426 (3)	C7—C8	1.311 (3)
N1—C9	1.377 (2)	C7—H7	0.9300
N1—C10	1.389 (3)	C8—C9	1.468 (3)
N1—H1A	0.8600	C8—H8	0.9300
N2—C10	1.314 (3)	C11—C12	1.503 (3)
N2—C11	1.449 (3)	C11—H11A	0.9700
N2—H2A	0.8600	C11—H11B	0.9700
N3—C16	1.450 (3)	C12—H12A	0.9700
N3—C13	1.453 (3)	C12—H12B	0.9700
N3—C12	1.460 (3)	C13—C14	1.500 (3)
C1—C6	1.375 (3)	C13—H13A	0.9700
C1—C2	1.380 (3)	C13—H13B	0.9700
C1—H1	0.9300	C14—H14A	0.9700
C2—C3	1.359 (3)	C14—H14B	0.9700
C2—H2	0.9300	C15—C16	1.492 (3)
C3—C4	1.352 (4)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.380 (3)	C16—H16A	0.9700
C4—H4	0.9300	C16—H16B	0.9700
C15—O2—C14	109.53 (16)	N2—C10—S1	124.57 (15)
C9—N1—C10	128.18 (17)	N1—C10—S1	119.00 (15)
C9—N1—H1A	115.9	N2—C11—C12	108.07 (17)
C10—N1—H1A	115.9	N2—C11—H11A	110.1
C10—N2—C11	124.72 (17)	C12—C11—H11A	110.1
C10—N2—H2A	117.6	N2—C11—H11B	110.1
C11—N2—H2A	117.6	C12—C11—H11B	110.1
C16—N3—C13	109.11 (17)	H11A—C11—H11B	108.4
C16—N3—C12	113.62 (17)	N3—C12—C11	111.27 (17)
C13—N3—C12	113.36 (17)	N3—C12—H12A	109.4
C6—C1—C2	120.7 (2)	C11—C12—H12A	109.4
C6—C1—H1	119.6	N3—C12—H12B	109.4
C2—C1—H1	119.6	C11—C12—H12B	109.4
C3—C2—C1	120.7 (2)	H12A—C12—H12B	108.0
C3—C2—H2	119.6	N3—C13—C14	110.20 (18)
C1—C2—H2	119.6	N3—C13—H13A	109.6
C4—C3—C2	119.7 (2)	C14—C13—H13A	109.6
C4—C3—H3	120.1	N3—C13—H13B	109.6
C2—C3—H3	120.1	C14—C13—H13B	109.6
C3—C4—C5	119.9 (2)	H13A—C13—H13B	108.1
C3—C4—H4	120.1	O2—C14—C13	111.9 (2)
C5—C4—H4	120.1	O2—C14—H14A	109.2
C4—C5—C6	121.6 (2)	C13—C14—H14A	109.2
C4—C5—H5	119.2	O2—C14—H14B	109.2
C6—C5—H5	119.2	C13—C14—H14B	109.2
C1—C6—C5	117.3 (2)	H14A—C14—H14B	107.9
C1—C6—C7	122.47 (19)	O2—C15—C16	111.33 (18)
C5—C6—C7	120.3 (2)	O2—C15—H15A	109.4
C8—C7—C6	127.4 (2)	C16—C15—H15A	109.4
C8—C7—H7	116.3	O2—C15—H15B	109.4
C6—C7—H7	116.3	C16—C15—H15B	109.4
C7—C8—C9	121.38 (19)	H15A—C15—H15B	108.0
C7—C8—H8	119.3	N3—C16—C15	109.23 (18)
C9—C8—H8	119.3	N3—C16—H16A	109.8
O1—C9—N1	122.43 (19)	C15—C16—H16A	109.8
O1—C9—C8	122.82 (18)	N3—C16—H16B	109.8
N1—C9—C8	114.75 (18)	C15—C16—H16B	109.8
N2—C10—N1	116.43 (17)	H16A—C16—H16B	108.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.95	2.642 (3)	136
N2—H2A···N3	0.86	2.39	2.758 (2)	107
C7—H7···O1	0.93	2.48	2.813 (3)	101
N1—H1A···O2^i	0.86	2.27	3.114 (2)	169
C15—H15B···S1^ii	0.97	2.81	3.731 (3)	159

Symmetry codes: (i) x, y+1, z; (ii) x−1, y−1, z.