Crystal structure of 1-{(Z)-[(2E)-3-(4-chloro­phen­yl)-1-phenyl­prop-2-en-1-yl­idene]amino}-3-ethyl­thio­urea

Tan, M.Y.; Crouse, K.A.; Ravoof, T.B.S.A.; Tiekink, E.R.T.

doi:10.1107/S2056989015023531

organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages o1047-o1048

https://doi.org/10.1107/S2056989015023531

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Crystal structure of 1-{(Z)-[(2E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-ethylthiourea

Ming Yueh Tan,^a Karen A. Crouse,^a Thahira Begum S. A. Ravoof ^a ^* and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^bCentre for Crystalline Materials, Faculty of Science and Technology, Sunway University, No. 5 Jalan Universiti, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
^*Correspondence e-mail: thahira@upm.edu.my, edwardt@sunway.edu.my

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 2 December 2015; accepted 8 December 2015; online 12 December 2015)

In the title thiosemicarbazone compound, C₁₈H₁₈ClN₃S, the CN₃S residue is almost planar (r.m.s. deviation = 0.0031 Å) and forms dihedral angles of 65.99 (7) and 34.60 (10)° with the phenyl and chlorobenzene rings, respectively; the dihedral angle between the aromatic rings is 85.13 (8)°. The conformation about the C=N bond is Z, and that about the C=C bonds is E. The imine N and ethyl N atoms are syn and are linked by an ethyl–imine N—H⋯N hydrogen bond. This H atom also forms an intermolecular hydrogen bond to the thione S atom, resulting in a supramolecular helical chain propagating along the b axis. The chains are consolidated into a three-dimensional architecture by phenyl-C—H⋯Cl contacts and weak π–π interactions between centrosymmetrically related chlorobenzene rings [inter-centroid distance = 3.9127 (15) Å].

Keywords: crystal structure; hydrogen bonding; thiosemicarbazone.

CCDC reference: 1441045

1. Related literature

For background to the coordination chemistry and applications of metal thiosemicarbazones, see: Dilworth & Hueting (2012 ). For the structure of a closely related thiosemicarbazone compound, 1-benzothiophene-2-carbaldehyde 4-ethylthiosemicarbazone, with almost planar semicarbazone units (two molecules comprise the asymmetric unit) and E conformations for the C=N bonds, see: Kayed et al. (2009 ).

2. Experimental

2.1. Crystal data

C₁₈H₁₈ClN₃S
M_r = 343.86
Monoclinic, P 2₁ /c
a = 10.580 (1) Å
b = 12.0438 (9) Å
c = 13.9561 (10) Å
β = 90.196 (8)°
V = 1778.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 293 K
0.20 × 0.15 × 0.10 mm

2.2. Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ) T_min = 0.800, T_max = 1.000
11178 measured reflections
4078 independent reflections
1963 reflections with I > 2σ(I)
R_int = 0.051

2.3. Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.120
S = 1.00
4078 reflections
216 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N3	0.88 (2)	2.25 (2)	2.629 (3)	106 (2)
N1—H1N⋯S1ⁱ	0.88 (2)	2.84 (2)	3.693 (2)	165 (2)
C43—H43⋯Cl1ⁱⁱ	0.93	2.82	3.708 (3)	160
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1441045

Crystal structure: contains datablocks 1, I. DOI: https://doi.org/10.1107/S2056989015023531/hb7555sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015023531/hb7555Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015023531/hb7555Isup3.cml

checkCIF report

Refinement top

Related literature top

For background to the coordination chemistry and applications of metal thiosemicarbazones, see: Dilworth & Hueting (2012). For the structure of a closely related thiosemicarbazone compound, 1-benzothiophene-2-carbaldehyde 4-ethylthiosemicarbazone, with almost planar semicarbazone units (two molecules comprise the asymmetric unit) and E conformations for the C═N bonds, see: Kayed et al. (2009).

Experimental top

An ethanol solution (20 ml) of 4-chlorochalcone (0.243 g, 1 mmol) was slowly added to a solution of 4-ethyl-3-thiosemicarbazide (0.119 g, 1 mmol) in absolute ethanol (20 ml), while stirring and heating for about 20 mins. The yellow precipitate was filtered, washed with cold ethanol and dried in vacuo. Light brown prisms of the title compound were grown at room temperature from the slow evaporation of a solvent mixture of dimethylformamide and acetonitrile; M.pt: 154–156 °C.

Structure description top

For background to the coordination chemistry and applications of metal thiosemicarbazones, see: Dilworth & Hueting (2012). For the structure of a closely related thiosemicarbazone compound, 1-benzothiophene-2-carbaldehyde 4-ethylthiosemicarbazone, with almost planar semicarbazone units (two molecules comprise the asymmetric unit) and E conformations for the C═N bonds, see: Kayed et al. (2009).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the helical supramolecular chain along the b axis and sustained by N—H···S hydrogen bonds shown as orange dashed lines.
	Fig. 3. A view of the unit cell contents in projection down the a axis. The N—H···S (orange), C—H···Cl (blue) and π—π (purple) interactions are shown as dashed lines.

1-{(Z)-[(2E)-3-(4-Chlorophenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-ethylthiourea top

Crystal data top

C₁₈H₁₈ClN₃S	F(000) = 720
M_r = 343.86	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.580 (1) Å	Cell parameters from 2181 reflections
b = 12.0438 (9) Å	θ = 2.9–27.5°
c = 13.9561 (10) Å	µ = 0.33 mm⁻¹
β = 90.196 (8)°	T = 293 K
V = 1778.3 (2) Å³	Prism, light-brown
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4078 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1963 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.051
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ω scan	h = −13→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −14→15
T_min = 0.800, T_max = 1.000	l = −18→18
11178 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.038	w = 1/[σ²(F_o²) + (0.0463P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.120	(Δ/σ)_max = 0.001
S = 1.00	Δρ_max = 0.20 e Å⁻³
4078 reflections	Δρ_min = −0.25 e Å⁻³
216 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2014), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0044 (7)

Crystal data top

C₁₈H₁₈ClN₃S	V = 1778.3 (2) Å³
M_r = 343.86	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.580 (1) Å	µ = 0.33 mm⁻¹
b = 12.0438 (9) Å	T = 293 K
c = 13.9561 (10) Å	0.20 × 0.15 × 0.10 mm
β = 90.196 (8)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4078 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	1963 reflections with I > 2σ(I)
T_min = 0.800, T_max = 1.000	R_int = 0.051
11178 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	2 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
4078 reflections	Δρ_min = −0.25 e Å⁻³
216 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	1.05835 (7)	−0.02341 (6)	0.20649 (5)	0.0606 (2)
Cl1	0.48690 (8)	0.72659 (6)	0.71676 (5)	0.0754 (3)
N1	1.0584 (2)	0.19712 (18)	0.23053 (16)	0.0579 (6)
H1N	1.025 (2)	0.2566 (14)	0.2562 (18)	0.070*
N2	0.9246 (2)	0.09776 (16)	0.32430 (15)	0.0543 (6)
H2N	0.900 (2)	0.0320 (11)	0.3439 (17)	0.065*
N3	0.88627 (18)	0.19560 (15)	0.36594 (14)	0.0484 (5)
C1	1.0138 (2)	0.0979 (2)	0.25424 (18)	0.0470 (6)
C2	1.1491 (2)	0.2179 (2)	0.1541 (2)	0.0636 (8)
H2A	1.2065	0.1553	0.1494	0.076*
H2B	1.1986	0.2832	0.1699	0.076*
C3	1.0860 (3)	0.2351 (4)	0.0601 (2)	0.1085 (13)
H3A	1.0393	0.1696	0.0431	0.163*
H3B	1.1485	0.2497	0.0121	0.163*
H3C	1.0292	0.2971	0.0643	0.163*
C4	0.8004 (2)	0.18918 (18)	0.43172 (16)	0.0420 (6)
C5	0.7641 (2)	0.29357 (18)	0.47552 (16)	0.0443 (6)
H5	0.8101	0.3565	0.4592	0.053*
C6	0.6697 (2)	0.30579 (18)	0.53736 (16)	0.0434 (6)
H6	0.6254	0.2419	0.5537	0.052*
C7	0.6281 (2)	0.40943 (18)	0.58244 (16)	0.0409 (6)
C8	0.5030 (2)	0.42061 (19)	0.61122 (16)	0.0463 (6)
H8	0.4477	0.3614	0.6026	0.056*
C9	0.4589 (3)	0.5176 (2)	0.65233 (16)	0.0517 (7)
H9	0.3749	0.5240	0.6708	0.062*
C10	0.5415 (3)	0.60409 (19)	0.66531 (16)	0.0504 (7)
C11	0.6661 (3)	0.5955 (2)	0.63902 (18)	0.0576 (7)
H11	0.7209	0.6548	0.6489	0.069*
C12	0.7099 (3)	0.49840 (19)	0.59786 (18)	0.0529 (7)
H12	0.7943	0.4925	0.5804	0.063*
C41	0.7411 (2)	0.08309 (17)	0.46264 (17)	0.0391 (6)
C42	0.6659 (2)	0.02282 (19)	0.39972 (17)	0.0446 (6)
H42	0.6525	0.0488	0.3377	0.054*
C43	0.6108 (2)	−0.07542 (19)	0.42866 (19)	0.0506 (7)
H43	0.5608	−0.1156	0.3860	0.061*
C44	0.6294 (2)	−0.1139 (2)	0.5200 (2)	0.0550 (7)
H44	0.5916	−0.1799	0.5394	0.066*
C45	0.7037 (2)	−0.0552 (2)	0.58311 (19)	0.0553 (7)
H45	0.7163	−0.0817	0.6450	0.066*
C46	0.7597 (2)	0.0428 (2)	0.55490 (17)	0.0491 (6)
H46	0.8101	0.0821	0.5978	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0614 (5)	0.0544 (4)	0.0661 (5)	0.0084 (3)	0.0204 (4)	−0.0080 (4)
Cl1	0.1222 (7)	0.0502 (4)	0.0539 (4)	0.0289 (4)	0.0068 (4)	−0.0074 (3)
N1	0.0567 (14)	0.0503 (14)	0.0670 (15)	−0.0007 (11)	0.0263 (12)	0.0014 (12)
N2	0.0638 (14)	0.0380 (12)	0.0614 (13)	0.0005 (10)	0.0292 (11)	−0.0016 (11)
N3	0.0531 (12)	0.0375 (11)	0.0548 (12)	0.0017 (9)	0.0176 (11)	−0.0023 (10)
C1	0.0433 (14)	0.0470 (16)	0.0506 (14)	0.0010 (11)	0.0098 (12)	−0.0017 (13)
C2	0.0500 (16)	0.0699 (18)	0.0710 (19)	−0.0065 (13)	0.0207 (15)	0.0061 (16)
C3	0.078 (2)	0.172 (4)	0.076 (2)	−0.021 (2)	0.006 (2)	0.031 (3)
C4	0.0426 (14)	0.0386 (14)	0.0450 (14)	−0.0014 (10)	0.0090 (12)	−0.0001 (12)
C5	0.0482 (15)	0.0349 (13)	0.0500 (14)	−0.0011 (10)	0.0094 (12)	−0.0001 (11)
C6	0.0465 (14)	0.0378 (14)	0.0459 (14)	−0.0015 (10)	0.0062 (12)	−0.0017 (11)
C7	0.0491 (15)	0.0368 (13)	0.0368 (13)	0.0022 (11)	0.0066 (11)	0.0014 (11)
C8	0.0537 (16)	0.0411 (14)	0.0442 (14)	0.0000 (11)	0.0115 (12)	0.0051 (12)
C9	0.0611 (17)	0.0494 (16)	0.0448 (15)	0.0155 (13)	0.0141 (13)	0.0075 (13)
C10	0.079 (2)	0.0373 (14)	0.0348 (13)	0.0122 (13)	0.0034 (13)	−0.0021 (12)
C11	0.0728 (19)	0.0446 (16)	0.0555 (16)	−0.0044 (13)	−0.0035 (15)	−0.0065 (14)
C12	0.0543 (17)	0.0489 (16)	0.0555 (16)	−0.0019 (12)	0.0096 (13)	−0.0080 (13)
C41	0.0404 (13)	0.0342 (13)	0.0427 (14)	0.0028 (10)	0.0110 (11)	−0.0028 (11)
C42	0.0470 (15)	0.0450 (14)	0.0419 (13)	0.0016 (11)	0.0075 (12)	−0.0019 (12)
C43	0.0538 (16)	0.0433 (14)	0.0547 (17)	−0.0066 (12)	0.0098 (13)	−0.0102 (13)
C44	0.0603 (17)	0.0396 (14)	0.0652 (18)	−0.0061 (12)	0.0154 (15)	0.0042 (14)
C45	0.0653 (18)	0.0503 (16)	0.0502 (15)	0.0011 (13)	0.0076 (14)	0.0104 (14)
C46	0.0532 (16)	0.0472 (15)	0.0469 (15)	−0.0046 (12)	0.0003 (12)	−0.0003 (13)

Geometric parameters (Å, º) top

S1—C1	1.674 (2)	C7—C8	1.392 (3)
Cl1—C10	1.740 (2)	C7—C12	1.393 (3)
N1—C1	1.327 (3)	C8—C9	1.383 (3)
N1—C2	1.459 (3)	C8—H8	0.9300
N1—H1N	0.874 (10)	C9—C10	1.372 (4)
N2—C1	1.361 (3)	C9—H9	0.9300
N2—N3	1.376 (2)	C10—C11	1.373 (4)
N2—H2N	0.878 (10)	C11—C12	1.384 (3)
N3—C4	1.296 (2)	C11—H11	0.9300
C2—C3	1.484 (4)	C12—H12	0.9300
C2—H2A	0.9700	C41—C42	1.388 (3)
C2—H2B	0.9700	C41—C46	1.389 (3)
C3—H3A	0.9600	C42—C43	1.380 (3)
C3—H3B	0.9600	C42—H42	0.9300
C3—H3C	0.9600	C43—C44	1.370 (3)
C4—C5	1.450 (3)	C43—H43	0.9300
C4—C41	1.488 (3)	C44—C45	1.375 (4)
C5—C6	1.330 (3)	C44—H44	0.9300
C5—H5	0.9300	C45—C46	1.379 (3)
C6—C7	1.466 (3)	C45—H45	0.9300
C6—H6	0.9300	C46—H46	0.9300

C1—N1—C2	124.9 (2)	C9—C8—C7	121.6 (2)
C1—N1—H1N	119.5 (17)	C9—C8—H8	119.2
C2—N1—H1N	115.1 (17)	C7—C8—H8	119.2
C1—N2—N3	120.56 (18)	C10—C9—C8	118.7 (2)
C1—N2—H2N	115.5 (16)	C10—C9—H9	120.6
N3—N2—H2N	123.6 (16)	C8—C9—H9	120.6
C4—N3—N2	117.15 (18)	C9—C10—C11	121.3 (2)
N1—C1—N2	115.3 (2)	C9—C10—Cl1	119.1 (2)
N1—C1—S1	125.86 (17)	C11—C10—Cl1	119.6 (2)
N2—C1—S1	118.80 (17)	C10—C11—C12	119.8 (2)
N1—C2—C3	112.0 (2)	C10—C11—H11	120.1
N1—C2—H2A	109.2	C12—C11—H11	120.1
C3—C2—H2A	109.2	C11—C12—C7	120.4 (2)
N1—C2—H2B	109.2	C11—C12—H12	119.8
C3—C2—H2B	109.2	C7—C12—H12	119.8
H2A—C2—H2B	107.9	C42—C41—C46	118.9 (2)
C2—C3—H3A	109.5	C42—C41—C4	120.5 (2)
C2—C3—H3B	109.5	C46—C41—C4	120.7 (2)
H3A—C3—H3B	109.5	C43—C42—C41	120.3 (2)
C2—C3—H3C	109.5	C43—C42—H42	119.8
H3A—C3—H3C	109.5	C41—C42—H42	119.8
H3B—C3—H3C	109.5	C44—C43—C42	120.2 (2)
N3—C4—C5	115.73 (19)	C44—C43—H43	119.9
N3—C4—C41	123.63 (19)	C42—C43—H43	119.9
C5—C4—C41	120.64 (18)	C43—C44—C45	120.1 (2)
C6—C5—C4	124.7 (2)	C43—C44—H44	119.9
C6—C5—H5	117.6	C45—C44—H44	119.9
C4—C5—H5	117.6	C44—C45—C46	120.2 (2)
C5—C6—C7	126.8 (2)	C44—C45—H45	119.9
C5—C6—H6	116.6	C46—C45—H45	119.9
C7—C6—H6	116.6	C45—C46—C41	120.2 (2)
C8—C7—C12	118.1 (2)	C45—C46—H46	119.9
C8—C7—C6	119.6 (2)	C41—C46—H46	119.9
C12—C7—C6	122.3 (2)

C1—N2—N3—C4	179.6 (2)	C9—C10—C11—C12	0.5 (4)
C2—N1—C1—N2	−176.5 (2)	Cl1—C10—C11—C12	−179.8 (2)
C2—N1—C1—S1	3.9 (4)	C10—C11—C12—C7	0.3 (4)
N3—N2—C1—N1	−0.2 (4)	C8—C7—C12—C11	−1.2 (4)
N3—N2—C1—S1	179.39 (19)	C6—C7—C12—C11	178.8 (2)
C1—N1—C2—C3	87.9 (4)	N3—C4—C41—C42	−65.7 (3)
N2—N3—C4—C5	178.8 (2)	C5—C4—C41—C42	114.7 (2)
N2—N3—C4—C41	−0.9 (4)	N3—C4—C41—C46	114.5 (3)
N3—C4—C5—C6	173.2 (2)	C5—C4—C41—C46	−65.2 (3)
C41—C4—C5—C6	−7.1 (4)	C46—C41—C42—C43	0.0 (3)
C4—C5—C6—C7	−179.0 (2)	C4—C41—C42—C43	−179.9 (2)
C5—C6—C7—C8	152.8 (2)	C41—C42—C43—C44	0.3 (3)
C5—C6—C7—C12	−27.2 (4)	C42—C43—C44—C45	−0.4 (4)
C12—C7—C8—C9	1.3 (3)	C43—C44—C45—C46	0.1 (4)
C6—C7—C8—C9	−178.7 (2)	C44—C45—C46—C41	0.2 (4)
C7—C8—C9—C10	−0.4 (4)	C42—C41—C46—C45	−0.2 (3)
C8—C9—C10—C11	−0.5 (4)	C4—C41—C46—C45	179.6 (2)
C8—C9—C10—Cl1	179.87 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3	0.88 (2)	2.25 (2)	2.629 (3)	106 (2)
N1—H1N···S1ⁱ	0.88 (2)	2.84 (2)	3.693 (2)	165 (2)
C43—H43···Cl1ⁱⁱ	0.93	2.82	3.708 (3)	160

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3	0.876 (19)	2.25 (2)	2.629 (3)	106.1 (15)
N1—H1N···S1ⁱ	0.876 (19)	2.841 (18)	3.693 (2)	164.5 (19)
C43—H43···Cl1ⁱⁱ	0.93	2.82	3.708 (3)	160

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2.

Acknowledgements

This research was funded by Universiti Putra Malaysia (UPM) under Research University Grant Schemes (RUGS No. 9419400), the Fundamental Research Grant Scheme (FRGS No. 5524425) and the Science Fund (Science Fund No. 06–01-04-SF810). MYT wishes to thank the UPM for the award of a Graduate Research Fellowship.

References

Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Dilworth, J. R. & Hueting, R. (2012). Inorg. Chim. Acta, 389, 3–15. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kayed, S. F., Farina, Y. & Simpson, J. (2009). Acta Cryst. E65, o180–o181. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 71| Part 12| December 2015| Pages o1047-o1048

https://doi.org/10.1107/S2056989015023531

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 1-{(Z)-[(2E)-3-(4-chloro­phen­yl)-1-phenyl­prop-2-en-1-yl­­idene]amino}-3-ethyl­thio­urea

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 1-{(Z)-[(2E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-ethylthiourea