Crystal structure of 2′-hy­droxy­aceto­phenone 4-methyl­thio­semicarbazide

Jamsari, J.; Abas, N.F.; Ravoof, T.B.S.A.; Tiekink, E.R.T.

doi:10.1107/S2056989015004958

organic compounds

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ISSN: 2056-9890

Volume 71| Part 4| April 2015| Pages o244-o245

doi:10.1107/S2056989015004958

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Crystal structure of 2′-hydroxyacetophenone 4-methylthiosemicarbazide

Junita Jamsari,^a Nur Fatihah Abas,^a Thahira Begum S. A. Ravoof ^a ^* and Edward R. T. Tiekink ^b

^aDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: thahira@upm.edu.my

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 9 March 2015; accepted 11 March 2015; online 18 March 2015)

In the organic molecule of the title hydrate, C₁₁H₁₅N₃OS·H₂O, {systematic name: 3-ethyl-1-{(E)-[1-(2-hydroxyphenyl)ethylidene]amino}thiourea monohydrate}, a dihedral angle of 5.39 (2)° is formed between the hydroxybenzene ring and the non-H atoms comprising the side chain (r.m.s. deviation = 0.0625 Å), with the major deviation from planarity noted for the terminal ethyl group [the C—N—C—C torsion angle = −172.17 (13)°]. The N—H H atoms are syn and an intramolecular hydroxy–imine O—H⋯N hydrogen bond is noted. In the crystal, the N-bonded H atoms form hydrogen bonds to symmetry-related water molecules, and the latter form donor interactions with the hydroxy O atom and with a hydroxybenzene ring, forming a O—H⋯π interaction. The hydrogen bonding leads to supramolecular tubes aligned along the b axis. The tubes are connected into layers via C—H⋯O interactions, and these stack along the c axis with no directional interactions between them.

Keywords: crystal structure; thiosemicarbazide; hydrogen bonding; O—H⋯π interactions.

CCDC reference: 1053189

1. Related literature

For background to thiosemicarbazones and their coordination chemistry, see: Mazlan et al. (2014 ). The conformational flexibility in these molecules is reflected in the structure of the 4-methyl derivative where one molecule comprising the asymmetric unit is approximately planar and the other exhibits a clear twist between the hydroxybenzene and side chain, and in the structure of the 6-methoxy derivative where these residues are almost normal to each other, see: Anderson et al. (2012 , 2014 ). For synthesis and methodology, see: Omar et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₁H₁₅N₃OS·H₂O
M_r = 255.33
Triclinic, $[P \overline 1]$
a = 6.7947 (5) Å
b = 8.5169 (8) Å
c = 11.1199 (9) Å
α = 84.948 (7)°
β = 81.825 (6)°
γ = 84.084 (7)°
V = 631.81 (9) Å³
Z = 2
Cu Kα radiation
μ = 2.25 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.10 mm

2.2. Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.923, T_max = 1.000
8119 measured reflections
2408 independent reflections
2187 reflections with I > 2σ(I)
R_int = 0.026

2.3. Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.095
S = 1.03
2408 reflections
171 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N2	0.84 (1)	1.76 (1)	2.5292 (16)	150 (2)
N1—H1N⋯O1Wⁱ	0.86 (2)	2.09 (2)	2.8918 (17)	156 (2)
N3—H3N⋯O1Wⁱ	0.87 (2)	2.16 (2)	2.9625 (18)	154 (2)
O1W—H1W⋯O1	0.84 (2)	1.96 (2)	2.7894 (16)	174 (2)
O1W—H2W⋯Cg1ⁱⁱ	0.83 (1)	2.86 (1)	3.4165 (13)	127 (1)
C5—H5⋯O1ⁱⁱⁱ	0.95	2.56	3.3702 (18)	143
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z; (iii) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2015 ); 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: 1053189

Crystal structure: contains datablocks 1, I. DOI: 10.1107/S2056989015004958/hb7380sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015004958/hb7380Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015004958/hb7380Isup3.cml

checkCIF report

Related literature top

For background to thiosemicarbazones and their coordination chemistry, see: Mazlan et al. (2014). The conformational flexibility in these molecules is reflected in the structure of the 4-methyl derivative where one molecule comprising the asymmetric unit is approximately planar and the other exhibits a clear twist between the hydroxybenzene and side chain, and in the structure of the 6-methoxy derivative where these residues are almost normal to each other, see: Anderson et al. (2012, 2014). For synthesis and methodology, see: Omar et al. (2014).

Experimental top

4-Methyl-3-thiosemicarbazide (0.02 mol) was dissolved in hot ethanol (95%; 40 ml). A solution of 0.02 mol of 2'-hydroxyacetophenone was added drop-wise into the first solution. The mixture was heated and stirred to reduce the volume to half of its initial volume. Then, it was allowed to stand at room temperature until a white crystalline precipitate formed. The precipitate was then collected and recrystallized from ethanol and dried over silica gel. Colourless crystals were obtained from the ethanolic solution. Yield: 92%. M.pt: 116 °C. Anal. Found (Calc): C: 56.1 (55.7); H: 5.9 (6.4); N: 18.5 (17.7).

Structure description top

For background to thiosemicarbazones and their coordination chemistry, see: Mazlan et al. (2014). The conformational flexibility in these molecules is reflected in the structure of the 4-methyl derivative where one molecule comprising the asymmetric unit is approximately planar and the other exhibits a clear twist between the hydroxybenzene and side chain, and in the structure of the 6-methoxy derivative where these residues are almost normal to each other, see: Anderson et al. (2012, 2014). For synthesis and methodology, see: Omar et al. (2014).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2015); 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 the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
	Fig. 2. Two views of the supramolecular tube along the b axis sustained by O—H···O, N—H···O and O—H···π hydrogen bonding, shown as orange, blue and purple dashed lines, respectively.
	Fig. 3. A view of the unit-cell contents in projection down the b axis. The O—H···O, N—H···O, O—H···π and C—H···O interactions are shown as orange, blue, purple and brown dashed lines, respectively.

3-Ethyl-1-[(E)-[1-(2-hydroxyphenyl)ethylidene]amino]thiourea monohydrate top

Crystal data top

C₁₁H₁₅N₃OS·H₂O	Z = 2
M_r = 255.33	F(000) = 272
Triclinic, P1	D_x = 1.342 Mg m⁻³
a = 6.7947 (5) Å	Cu Kα radiation, λ = 1.5418 Å
b = 8.5169 (8) Å	Cell parameters from 4230 reflections
c = 11.1199 (9) Å	θ = 4.0–71.4°
α = 84.948 (7)°	µ = 2.25 mm⁻¹
β = 81.825 (6)°	T = 100 K
γ = 84.084 (7)°	Prism, pale-yellow
V = 631.81 (9) Å³	0.30 × 0.20 × 0.10 mm

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	2408 independent reflections
Radiation source: fine-focus sealed tube	2187 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 16.1952 pixels mm^-1	θ_max = 71.5°, θ_min = 4.0°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→9
T_min = 0.923, T_max = 1.000	l = −13→13
8119 measured reflections

Refinement top

Refinement on F²	6 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0593P)² + 0.1686P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2408 reflections	Δρ_max = 0.33 e Å⁻³
171 parameters	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₁H₁₅N₃OS·H₂O	γ = 84.084 (7)°
M_r = 255.33	V = 631.81 (9) Å³
Triclinic, P1	Z = 2
a = 6.7947 (5) Å	Cu Kα radiation
b = 8.5169 (8) Å	µ = 2.25 mm⁻¹
c = 11.1199 (9) Å	T = 100 K
α = 84.948 (7)°	0.30 × 0.20 × 0.10 mm
β = 81.825 (6)°

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	2408 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2187 reflections with I > 2σ(I)
T_min = 0.923, T_max = 1.000	R_int = 0.026
8119 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	6 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.33 e Å⁻³
2408 reflections	Δρ_min = −0.25 e Å⁻³
171 parameters

Special details top

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

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

	x	y	z	U_iso*/U_eq
S1	0.28553 (5)	0.84923 (4)	0.30332 (3)	0.01932 (14)
O1	0.34603 (16)	0.67711 (12)	0.02373 (9)	0.0193 (2)
H1O	0.325 (3)	0.7637 (15)	0.0568 (16)	0.029*
N1	0.24861 (18)	1.08372 (15)	0.12735 (11)	0.0163 (3)
H1N	0.224 (3)	1.1825 (17)	0.1053 (16)	0.020*
N2	0.26593 (17)	0.97046 (14)	0.04679 (11)	0.0150 (3)
N3	0.24119 (18)	1.16243 (16)	0.31656 (11)	0.0174 (3)
H3N	0.227 (3)	1.2558 (18)	0.2795 (15)	0.021*
C1	0.2583 (2)	1.03944 (18)	0.24810 (13)	0.0160 (3)
C2	0.2391 (2)	1.00570 (18)	−0.06558 (13)	0.0153 (3)
C2'	0.1872 (2)	1.16980 (18)	−0.12094 (13)	0.0192 (3)
H2'1	0.1497	1.2423	−0.0561	0.029*
H2'2	0.0750	1.1686	−0.1672	0.029*
H2'3	0.3030	1.2053	−0.1755	0.029*
C3	0.2674 (2)	0.86995 (18)	−0.14260 (13)	0.0154 (3)
C4	0.3216 (2)	0.71390 (18)	−0.09556 (13)	0.0164 (3)
C5	0.3532 (2)	0.58929 (18)	−0.17128 (14)	0.0193 (3)
H5	0.3914	0.4854	−0.1391	0.023*
C6	0.3291 (2)	0.61601 (19)	−0.29349 (14)	0.0214 (3)
H6	0.3503	0.5303	−0.3445	0.026*
C7	0.2739 (2)	0.76788 (19)	−0.34155 (13)	0.0206 (3)
H7	0.2562	0.7863	−0.4250	0.025*
C8	0.2451 (2)	0.89188 (19)	−0.26665 (13)	0.0179 (3)
H8	0.2089	0.9955	−0.3004	0.021*
C9	0.2364 (2)	1.14844 (19)	0.44845 (13)	0.0202 (3)
H9A	0.3678	1.1022	0.4697	0.024*
H9B	0.1344	1.0773	0.4859	0.024*
C10	0.1872 (3)	1.3101 (2)	0.49712 (14)	0.0271 (4)
H10A	0.2892	1.3797	0.4605	0.041*
H10B	0.1840	1.3003	0.5858	0.041*
H10C	0.0563	1.3549	0.4766	0.041*
O1W	0.14391 (17)	0.42112 (13)	0.13237 (11)	0.0243 (3)
H1W	0.200 (3)	0.5018 (17)	0.1042 (17)	0.036*
H2W	0.0232 (16)	0.452 (2)	0.1447 (19)	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0267 (2)	0.0159 (2)	0.01519 (19)	−0.00163 (15)	−0.00399 (14)	0.00149 (14)
O1	0.0279 (6)	0.0139 (5)	0.0164 (5)	−0.0010 (4)	−0.0056 (4)	0.0005 (4)
N1	0.0221 (6)	0.0121 (6)	0.0147 (6)	−0.0017 (5)	−0.0036 (5)	0.0003 (5)
N2	0.0142 (6)	0.0156 (6)	0.0151 (6)	−0.0024 (5)	−0.0014 (4)	−0.0012 (5)
N3	0.0215 (6)	0.0155 (7)	0.0151 (6)	−0.0020 (5)	−0.0033 (5)	0.0005 (5)
C1	0.0126 (6)	0.0191 (8)	0.0166 (7)	−0.0030 (6)	−0.0022 (5)	−0.0002 (6)
C2	0.0126 (6)	0.0168 (8)	0.0165 (7)	−0.0037 (5)	−0.0014 (5)	0.0014 (6)
C2'	0.0239 (7)	0.0174 (8)	0.0164 (7)	−0.0017 (6)	−0.0036 (6)	−0.0003 (6)
C3	0.0120 (6)	0.0179 (8)	0.0164 (7)	−0.0034 (5)	−0.0016 (5)	−0.0007 (6)
C4	0.0146 (6)	0.0187 (8)	0.0162 (7)	−0.0045 (6)	−0.0028 (5)	0.0017 (6)
C5	0.0191 (7)	0.0152 (8)	0.0239 (7)	−0.0037 (6)	−0.0032 (6)	−0.0006 (6)
C6	0.0202 (7)	0.0235 (9)	0.0218 (7)	−0.0070 (6)	−0.0013 (6)	−0.0066 (6)
C7	0.0198 (7)	0.0276 (9)	0.0156 (7)	−0.0063 (6)	−0.0036 (5)	−0.0014 (6)
C8	0.0162 (7)	0.0194 (8)	0.0179 (7)	−0.0027 (6)	−0.0027 (5)	0.0021 (6)
C9	0.0232 (7)	0.0228 (8)	0.0151 (7)	−0.0049 (6)	−0.0028 (5)	−0.0006 (6)
C10	0.0361 (9)	0.0257 (9)	0.0204 (8)	−0.0072 (7)	−0.0004 (6)	−0.0072 (6)
O1W	0.0227 (6)	0.0173 (6)	0.0314 (6)	−0.0025 (5)	−0.0014 (5)	0.0029 (5)

Geometric parameters (Å, º) top

S1—C1	1.6825 (16)	C4—C5	1.393 (2)
O1—C4	1.3653 (17)	C5—C6	1.388 (2)
O1—H1O	0.843 (9)	C5—H5	0.9500
N1—N2	1.3586 (17)	C6—C7	1.391 (2)
N1—C1	1.3713 (18)	C6—H6	0.9500
N1—H1N	0.862 (14)	C7—C8	1.383 (2)
N2—C2	1.2931 (18)	C7—H7	0.9500
N3—C1	1.3344 (19)	C8—H8	0.9500
N3—C9	1.4569 (18)	C9—C10	1.511 (2)
N3—H3N	0.865 (14)	C9—H9A	0.9900
C2—C3	1.480 (2)	C9—H9B	0.9900
C2—C2'	1.505 (2)	C10—H10A	0.9800
C2'—H2'1	0.9800	C10—H10B	0.9800
C2'—H2'2	0.9800	C10—H10C	0.9800
C2'—H2'3	0.9800	O1W—H1W	0.834 (9)
C3—C8	1.403 (2)	O1W—H2W	0.831 (9)
C3—C4	1.417 (2)

C4—O1—H1O	105.5 (13)	C6—C5—C4	120.42 (14)
N2—N1—C1	119.33 (12)	C6—C5—H5	119.8
N2—N1—H1N	121.6 (12)	C4—C5—H5	119.8
C1—N1—H1N	119.0 (12)	C5—C6—C7	120.19 (14)
C2—N2—N1	121.39 (13)	C5—C6—H6	119.9
C1—N3—C9	124.21 (13)	C7—C6—H6	119.9
C1—N3—H3N	116.9 (12)	C8—C7—C6	119.35 (13)
C9—N3—H3N	118.8 (12)	C8—C7—H7	120.3
N3—C1—N1	112.99 (13)	C6—C7—H7	120.3
N3—C1—S1	123.95 (11)	C7—C8—C3	122.27 (14)
N1—C1—S1	123.06 (11)	C7—C8—H8	118.9
N2—C2—C3	115.00 (13)	C3—C8—H8	118.9
N2—C2—C2'	125.29 (13)	N3—C9—C10	109.63 (13)
C3—C2—C2'	119.70 (12)	N3—C9—H9A	109.7
C2—C2'—H2'1	109.5	C10—C9—H9A	109.7
C2—C2'—H2'2	109.5	N3—C9—H9B	109.7
H2'1—C2'—H2'2	109.5	C10—C9—H9B	109.7
C2—C2'—H2'3	109.5	H9A—C9—H9B	108.2
H2'1—C2'—H2'3	109.5	C9—C10—H10A	109.5
H2'2—C2'—H2'3	109.5	C9—C10—H10B	109.5
C8—C3—C4	117.28 (13)	H10A—C10—H10B	109.5
C8—C3—C2	120.87 (13)	C9—C10—H10C	109.5
C4—C3—C2	121.84 (13)	H10A—C10—H10C	109.5
O1—C4—C5	116.68 (13)	H10B—C10—H10C	109.5
O1—C4—C3	122.84 (13)	H1W—O1W—H2W	105 (2)
C5—C4—C3	120.48 (13)

C1—N1—N2—C2	173.45 (12)	C2—C3—C4—O1	1.8 (2)
C9—N3—C1—N1	176.76 (12)	C8—C3—C4—C5	0.8 (2)
C9—N3—C1—S1	−2.4 (2)	C2—C3—C4—C5	−177.99 (12)
N2—N1—C1—N3	179.36 (12)	O1—C4—C5—C6	179.21 (12)
N2—N1—C1—S1	−1.51 (19)	C3—C4—C5—C6	−1.0 (2)
N1—N2—C2—C3	178.75 (11)	C4—C5—C6—C7	0.3 (2)
N1—N2—C2—C2'	0.0 (2)	C5—C6—C7—C8	0.6 (2)
N2—C2—C3—C8	−179.27 (12)	C6—C7—C8—C3	−0.7 (2)
C2'—C2—C3—C8	−0.4 (2)	C4—C3—C8—C7	0.1 (2)
N2—C2—C3—C4	−0.5 (2)	C2—C3—C8—C7	178.85 (13)
C2'—C2—C3—C4	178.29 (12)	C1—N3—C9—C10	−172.17 (13)
C8—C3—C4—O1	−179.39 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2	0.84 (1)	1.76 (1)	2.5292 (16)	150 (2)
N1—H1N···O1Wⁱ	0.86 (2)	2.09 (2)	2.8918 (17)	156 (2)
N3—H3N···O1Wⁱ	0.87 (2)	2.16 (2)	2.9625 (18)	154 (2)
O1W—H1W···O1	0.84 (2)	1.96 (2)	2.7894 (16)	174 (2)
O1W—H2W···Cg1ⁱⁱ	0.83 (1)	2.86 (1)	3.4165 (13)	127 (1)
C5—H5···O1ⁱⁱⁱ	0.95	2.56	3.3702 (18)	143

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2	0.843 (14)	1.763 (13)	2.5292 (16)	150.2 (17)
N1—H1N···O1Wⁱ	0.862 (15)	2.086 (15)	2.8918 (17)	155.5 (16)
N3—H3N···O1Wⁱ	0.866 (16)	2.161 (17)	2.9625 (18)	153.8 (16)
O1W—H1W···O1	0.835 (17)	1.958 (17)	2.7894 (16)	173.7 (17)
O1W—H2W···Cg1ⁱⁱ	0.831 (13)	2.856 (14)	3.4165 (13)	126.5 (14)
C5—H5···O1ⁱⁱⁱ	0.95	2.56	3.3702 (18)	143

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

Acknowledgements

Support for this project came from Universiti Putra Malaysia (UPM) under their Research University Grant Scheme (RUGS No. 9419400), Malaysian Fundamental Research Grant Scheme (FRGS No. 5524425) and the ScienceFund (Science Fund No. 5450726). We also thank Siti Khadijah Densabali for collecting the X-ray data. JJ wishes to acknowledge the Malaysian Government for sponsorship under the SGRA Scheme.

References

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ISSN: 2056-9890

Volume 71| Part 4| April 2015| Pages o244-o245

doi:10.1107/S2056989015004958

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