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

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ISSN: 2414-3146

3-(2-Hy­dr­oxy­eth­yl)-3-methyl-1-(4-methyl­benzo­yl)thio­urea

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and bCentre for Crystalline Materials, Faculty of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
*Correspondence e-mail: edwardt@sunway.edu.my

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 16 December 2015; accepted 21 December 2015; online 12 January 2016)

The title thio­urea derivative, C12H16N2O2S, has a twisted conformation with the dihedral angle between the NC(=S)N and O=CC6 planes being 35.45 (5)°. The observed conformation allows for an intra­molecular N—H⋯O hydrogen bond. In the mol­ecular packing, supra­molecular aggregation is based on hy­droxy-O—H⋯O(carbon­yl) hydrogen bonding and leads to supra­molecular helical chains along the a axis; chains are reinforced by N-methyl­ene-C—H⋯S and N-methyl-C—H⋯π(arene) inter­actions. Supra­molecular layers in the ab plane are formed as a result of tolyl-methyl-C—H⋯π(arene) inter­actions.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Inter­est in the title compound arises from promising cytotoxicity profiles exhibited by palladium(II) (Selvakumaran et al., 2011[Selvakumaran, N., Ng, S. W., Tiekink, E. R. T. & Karvembu, R. (2011). Inorg. Chim. Acta, 376, 278-284.]) and copper(I) (Rauf et al., 2009[Rauf, M. K., Imtiaz-ud-Din, Badshah, A., Gielen, M., Ebihara, M., de Vos, D. & Ahmed, S. (2009). J. Inorg. Biochem. 103, 1135-1144.]) complexes of related N,N-di(alk­yl/ar­yl)-N′-benzoyl­thio­urea derivatives. The mol­ecular structure of the title compound, Fig. 1[link], comprises planar NC(=S)N (r.m.s. deviation = 0.0130 Å) and O=CC6 (r.m.s. deviation = 0.0068 Å) residues which form a dihedral angle of 35.45 (5)°. The N1—C2—C3—O1 torsion of 66.9 (2)° places the hy­droxy-O1 atom in close proximity to the amide enabling the formation of an intra­molecular N2—H⋯O1 hydrogen bond, Table 1[link].

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C6–C11 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2N⋯O1 0.87 (2) 2.02 (2) 2.838 (3) 157 (2)
O1—H1O⋯O2i 0.84 (2) 1.95 (2) 2.750 (2) 160 (2)
C2—H2B⋯S1ii 0.97 2.83 3.783 (3) 167
C4—H4BCg1iii 0.96 2.67 3.605 (3) 164
C12—H12ACg1iv 0.96 3.00 3.932 (3) 164
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iii) [-x-1, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]; (iv) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].
[Figure 1]
Figure 1
The mol­ecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. The dashed line represents the intra­molecular N—H⋯O hydrogen bond.

In the crystal, supra­molecular helical chains are formed along the a axis and are sustained by a combination of hy­droxy-O—H⋯O(carbon­yl) hydrogen bonding, and N-methyl­ene-C—H⋯S and N-methyl-C—H⋯π(arene) inter­actions. Connections between the chains are of the type tolyl-methyl-C—H⋯π(arene) and occur along the b axis resulting in a supra­molecular layer, Fig. 2[link]. The layers pack along the c axis with no directional inter­actions between them.

[Figure 2]
Figure 2
A view of the supra­molecular layer in the ab plane in the crystal structure of the title compound shown in projection down the c axis. The O—H⋯O, C—H⋯S and C—H⋯π inter­actions are shown as orange, blue and purple dashed lines, respectively.

The most closely related mol­ecule in the literature, i.e. with N-ethyl, rather than N-methyl, and 2-tolyl rather than 4-tolyl (Yamin et al., 2014[Yamin, B. M., Hizam, S. M. M., Yusoff, S. F. M. & Hasbullah, S. A. (2014). Acta Cryst. E70, o602.]), has an almost identical conformation with the exception of the relative orientation of the tolyl rings. Thus, the dihedral angle between the NC(=S)N and O=CC6 planes in the literature structure is 22.75 (5)° cf. 35.45 (5)° in the title compound. The mol­ecular packing differs also in that although hy­droxy-O—H⋯O(carbon­yl) hydrogen bonding persist, they lead to zigzag chains (glide symmetry).

Synthesis and crystallization

A procedure based on a literature precedent (Rauf et al., 2009[Rauf, M. K., Imtiaz-ud-Din, Badshah, A., Gielen, M., Ebihara, M., de Vos, D. & Ahmed, S. (2009). J. Inorg. Biochem. 103, 1135-1144.]) was employed in the synthesis of the title compound. Thus, an excess of thionyl chloride was mixed with 4-methyl­benzoic acid (1 mmol) and the solution refluxed until a pale-yellow solution was obtained. The excess thionyl chloride was removed on a water bath, leaving only 4-methyl­benzoyl chloride, which is a viscous, yellow liquid. Ammonium thio­cyanate (1 mmol) was added to a stirred acetone solution of 4-methyl­benzoyl chloride (1 mmol), yielding a pink solution which turned yellow upon stirring for 2 h. The white precipitate (ammonium chloride) was isolated upon filtration and to the yellow filtrate, N-methyl-N-(hy­droxy­eth­yl)amine was carefully added and stirring continued for another 1 h. Upon the addition of water, a yellow precipitate was obtained. This was collected by filtration and recrystallized from hot acetone solution, yielding yellow blocks.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C12H16N2O2S
Mr 252.33
Crystal system, space group Orthorhombic, P212121
Temperature (K) 296
a, b, c (Å) 7.351 (3), 12.452 (4), 13.423 (5)
V3) 1228.8 (7)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.26
Crystal size (mm) 0.20 × 0.16 × 0.15
 
Data collection
Diffractometer Bruker SMART APEX diffractometer
Absorption correction Multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.])
Tmin, Tmax 0.951, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections 7036, 2790, 2637
Rint 0.031
(sin θ/λ)max−1) 0.649
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.073, 1.02
No. of reflections 2790
No. of parameters 162
No. of restraints 2
Δρmax, Δρmin (e Å−3) 0.18, −0.25
Absolute structure Flack x determined using 1054 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter 0.10 (4)
Computer programs: SMART (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]), publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Synthesis and crystallization top

A procedure based on a literature precedent (Rauf et al., 2009) was employed in the synthesis of the title compound. Thus, an excess of thio­nyl chloride was mixed with 4-methyl­benzoic acid (1 mmol) and the solution refluxed until a pale-yellow solution was obtained. The excess thio­nyl chloride was removed on a water bath, leaving only 4-methyl­benzoyl chloride, which is a viscous, yellow liquid. Ammonium thio­cyanate (1 mmol) was added to a stirred acetone solution of 4-methyl­benzoyl chloride (1 mmol), yielding a pink solution which turned yellow upon stirring for 2 h. The white precipitate (ammonium chloride) was isolated upon filtration and to the yellow filtrate, N-methyl-N-(hy­droxy­ethyl)­amine was carefully added and stirring continued for another 1 h. Upon the addition of water, a yellow precipitate was obtained. This was collected by filtration and recrystallized from hot acetone solution, yielding yellow blocks.

Refinement top

The carbon-bound H-atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Uequiv(C). The oxygen and nitro­gen-bound H-atoms were located in a difference Fourier map but were refined with a distance restraints of O—H = 0.84±0.01 Å and N—H = 0.88±0.01 Å, and with Uiso(H) set to 1.5Uequiv(O) or 1.2Uequiv(N).

Experimental top

A procedure based on a literature precedent (Rauf et al., 2009) was employed in the synthesis of the title compound. Thus, an excess of thionyl chloride was mixed with 4-methylbenzoic acid (1 mmol) and the solution refluxed until a pale-yellow solution was obtained. The excess thionyl chloride was removed on a water bath, leaving only 4-methylbenzoyl chloride, which is a viscous, yellow liquid. Ammonium thiocyanate (1 mmol) was added to a stirred acetone solution of 4-methylbenzoyl chloride (1 mmol), yielding a pink solution which turned yellow upon stirring for 2 h. The white precipitate (ammonium chloride) was isolated upon filtration and to the yellow filtrate, N-methyl-N-(hydroxyethyl)amine was carefully added and stirring continued for another 1 h. Upon the addition of water, a yellow precipitate was obtained. This was collected by filtration and recrystallized from hot acetone solution, yielding yellow blocks.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2.

Structure description top

Interest in the title compound arises from promising cytotoxicity profiles exhibited by palladium(II) (Selvakumaran et al., 2011) and copper(I) (Rauf et al., 2009) complexes of related N,N-di(alkyl/aryl)-N'-benzoylthiourea derivatives. The molecular structure of the title compound, Fig. 1, comprises planar NC( S)N (r.m.s. deviation = 0.0130 Å) and OCC6 (r.m.s. deviation = 0.0068 Å) residues which form a dihedral angle of 35.45 (5)°. The N1—C2—C3—O1 torsion of 66.9 (2)° places the hydroxy-O1 atom in close proximity to the amide enabling the formation of an intramolecular N2—H···O1 hydrogen bond, Table 1.

In the crystal, supramolecular helical chains are formed along the a axis and are sustained by a combination of hydroxy-O—H···O(carbonyl) hydrogen bonding, and N-methylene-C—H···S and N-methyl-C—H···π(arene) interactions. Connections between the chains are of the type tolyl-methyl-C—H···π(arene) and occur along the b axis resulting in a supramolecular layer, Fig.2. The layers pack along the c axis with no directional interactions between them.

The most closely related molecule in the literature, i.e. with N-ethyl, rather than N-methyl, and 2-tolyl rather than 4-tolyl (Yamin et al., 2014), has an almost identical conformation with the exception of the relative orientation of the tolyl rings. Thus, the dihedral angle between the NC(S)N and OCC6 planes in the literature structure is 22.75 (5)° cf. 35.45 (5)° in the title compound. The molecular packing differs also in that although hydroxy-O—H···O(carbonyl) hydrogen bonding persist, they lead to zigzag chains (glide symmetry).

Computing details top

Data collection: SMART (Bruker, 2009); cell refinement: SMART (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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
[Figure 1] Fig. 1. The molecular structures of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. The dashed line represents the intramolecular N—H···O hydrogen bond.
[Figure 2] Fig. 2. A view of the supramolecular layer in the ab plane in the crystal structure of the title compound shown in projection down the c axis. The O—H···O, C—H···S and C—H···π interactions are shown as orange, blue and purple dashed lines, respectively.
3-(2-Hydroxyethyl)-3-methyl-1-(4-methylbenzoyl)thiourea top
Crystal data top
C12H16N2O2SDx = 1.364 Mg m3
Mr = 252.33Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 2964 reflections
a = 7.351 (3) Åθ = 2.2–29.9°
b = 12.452 (4) ŵ = 0.26 mm1
c = 13.423 (5) ÅT = 296 K
V = 1228.8 (7) Å3Block, yellow
Z = 40.20 × 0.16 × 0.15 mm
F(000) = 536
Data collection top
Bruker SMART APEX
diffractometer
2790 independent reflections
Radiation source: fine-focus sealed tube2637 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.951, Tmax = 0.963k = 1616
7036 measured reflectionsl = 1710
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0336P)2 + 0.2556P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.031(Δ/σ)max = 0.001
wR(F2) = 0.073Δρmax = 0.18 e Å3
S = 1.02Δρmin = 0.25 e Å3
2790 reflectionsAbsolute structure: Flack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
162 parametersAbsolute structure parameter: 0.10 (4)
2 restraints
Crystal data top
C12H16N2O2SV = 1228.8 (7) Å3
Mr = 252.33Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.351 (3) ŵ = 0.26 mm1
b = 12.452 (4) ÅT = 296 K
c = 13.423 (5) Å0.20 × 0.16 × 0.15 mm
Data collection top
Bruker SMART APEX
diffractometer
2790 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2637 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.963Rint = 0.031
7036 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0312 restraints
wR(F2) = 0.073Δρmax = 0.18 e Å3
S = 1.02Δρmin = 0.25 e Å3
2790 reflectionsAbsolute structure: Flack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
162 parametersAbsolute structure parameter: 0.10 (4)
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
xyzUiso*/Ueq
S11.01508 (8)0.90725 (4)0.57485 (4)0.01773 (14)
O11.1122 (2)0.66072 (11)0.30188 (12)0.0179 (3)
H1O1.208 (3)0.6932 (19)0.3173 (19)0.027*
O20.8730 (2)0.68828 (12)0.65388 (11)0.0188 (3)
N10.9313 (2)0.85435 (14)0.38890 (14)0.0151 (4)
N20.9723 (3)0.71025 (12)0.49351 (13)0.0154 (4)
H2N1.007 (3)0.6768 (17)0.4400 (12)0.019*
C10.9672 (3)0.82250 (15)0.48229 (15)0.0143 (4)
C20.8567 (3)0.78372 (17)0.31094 (16)0.0170 (5)
H2A0.77430.82490.26940.020*
H2B0.78710.72680.34220.020*
C31.0032 (3)0.73413 (16)0.24575 (15)0.0183 (4)
H3B0.94680.69650.19050.022*
H3C1.07980.79040.21870.022*
C40.9624 (3)0.96612 (16)0.35912 (17)0.0190 (5)
H4A1.06890.99310.39210.028*
H4B0.85901.00890.37740.028*
H4C0.97970.96960.28830.028*
C50.9380 (3)0.65102 (16)0.57733 (17)0.0142 (4)
C60.9851 (3)0.53401 (15)0.57083 (16)0.0140 (4)
C71.0600 (3)0.48527 (17)0.48678 (16)0.0158 (4)
H71.08270.52580.42990.019*
C81.1007 (3)0.37630 (16)0.48775 (17)0.0172 (5)
H81.15180.34480.43150.021*
C91.0662 (3)0.31339 (16)0.57154 (18)0.0164 (4)
C100.9946 (3)0.36278 (16)0.65533 (16)0.0170 (4)
H100.97320.32240.71240.020*
C110.9544 (3)0.47186 (16)0.65537 (17)0.0161 (4)
H110.90660.50360.71240.019*
C121.1028 (3)0.19392 (16)0.56988 (19)0.0201 (5)
H12A1.21510.18040.53560.030*
H12B1.00530.15790.53600.030*
H12C1.11130.16760.63700.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0235 (3)0.0120 (2)0.0178 (3)0.0004 (2)0.0022 (3)0.00127 (19)
O10.0193 (8)0.0168 (8)0.0176 (8)0.0015 (6)0.0009 (7)0.0000 (6)
O20.0250 (8)0.0139 (7)0.0177 (8)0.0026 (6)0.0046 (7)0.0007 (6)
N10.0182 (9)0.0122 (8)0.0148 (9)0.0000 (7)0.0014 (7)0.0019 (7)
N20.0218 (10)0.0111 (7)0.0134 (8)0.0009 (7)0.0018 (8)0.0009 (6)
C10.0124 (10)0.0130 (9)0.0175 (10)0.0009 (8)0.0014 (8)0.0008 (8)
C20.0178 (10)0.0165 (10)0.0167 (12)0.0017 (8)0.0040 (9)0.0012 (8)
C30.0242 (11)0.0165 (9)0.0142 (10)0.0019 (9)0.0018 (10)0.0014 (7)
C40.0237 (12)0.0131 (9)0.0202 (11)0.0003 (9)0.0022 (10)0.0053 (8)
C50.0132 (9)0.0131 (9)0.0163 (10)0.0006 (7)0.0016 (9)0.0003 (8)
C60.0131 (9)0.0125 (8)0.0163 (10)0.0001 (8)0.0023 (10)0.0011 (7)
C70.0184 (11)0.0159 (9)0.0132 (11)0.0026 (8)0.0009 (9)0.0014 (8)
C80.0177 (11)0.0169 (10)0.0170 (12)0.0008 (8)0.0006 (9)0.0028 (8)
C90.0136 (9)0.0122 (9)0.0234 (11)0.0003 (7)0.0043 (9)0.0013 (9)
C100.0179 (10)0.0151 (9)0.0182 (10)0.0001 (9)0.0005 (10)0.0037 (8)
C110.0165 (10)0.0167 (9)0.0150 (10)0.0003 (8)0.0017 (9)0.0014 (8)
C120.0218 (11)0.0129 (9)0.0257 (12)0.0016 (8)0.0003 (10)0.0003 (10)
Geometric parameters (Å, º) top
S1—C11.668 (2)C4—H4C0.9600
O1—C31.430 (3)C5—C61.500 (3)
O1—H1O0.838 (13)C6—C111.392 (3)
O2—C51.225 (3)C6—C71.394 (3)
N1—C11.341 (3)C7—C81.390 (3)
N1—C41.466 (3)C7—H70.9300
N1—C21.473 (3)C8—C91.394 (3)
N2—C51.369 (3)C8—H80.9300
N2—C11.406 (2)C9—C101.386 (3)
N2—H2N0.868 (12)C9—C121.512 (3)
C2—C31.518 (3)C10—C111.390 (3)
C2—H2A0.9700C10—H100.9300
C2—H2B0.9700C11—H110.9300
C3—H3B0.9700C12—H12A0.9600
C3—H3C0.9700C12—H12B0.9600
C4—H4A0.9600C12—H12C0.9600
C4—H4B0.9600
C3—O1—H1O107.1 (18)O2—C5—N2123.87 (18)
C1—N1—C4120.34 (18)O2—C5—C6120.45 (19)
C1—N1—C2124.11 (17)N2—C5—C6115.68 (18)
C4—N1—C2115.54 (17)C11—C6—C7118.79 (18)
C5—N2—C1128.23 (18)C11—C6—C5117.08 (19)
C5—N2—H2N118.4 (15)C7—C6—C5124.11 (19)
C1—N2—H2N113.3 (15)C8—C7—C6120.2 (2)
N1—C1—N2113.53 (18)C8—C7—H7119.9
N1—C1—S1123.42 (15)C6—C7—H7119.9
N2—C1—S1122.93 (15)C7—C8—C9121.1 (2)
N1—C2—C3112.86 (18)C7—C8—H8119.4
N1—C2—H2A109.0C9—C8—H8119.4
C3—C2—H2A109.0C10—C9—C8118.33 (19)
N1—C2—H2B109.0C10—C9—C12121.1 (2)
C3—C2—H2B109.0C8—C9—C12120.6 (2)
H2A—C2—H2B107.8C9—C10—C11121.0 (2)
O1—C3—C2110.70 (17)C9—C10—H10119.5
O1—C3—H3B109.5C11—C10—H10119.5
C2—C3—H3B109.5C10—C11—C6120.6 (2)
O1—C3—H3C109.5C10—C11—H11119.7
C2—C3—H3C109.5C6—C11—H11119.7
H3B—C3—H3C108.1C9—C12—H12A109.5
N1—C4—H4A109.5C9—C12—H12B109.5
N1—C4—H4B109.5H12A—C12—H12B109.5
H4A—C4—H4B109.5C9—C12—H12C109.5
N1—C4—H4C109.5H12A—C12—H12C109.5
H4A—C4—H4C109.5H12B—C12—H12C109.5
H4B—C4—H4C109.5
C4—N1—C1—N2165.77 (19)O2—C5—C6—C7179.8 (2)
C2—N1—C1—N215.5 (3)N2—C5—C6—C70.4 (3)
C4—N1—C1—S110.3 (3)C11—C6—C7—C80.8 (3)
C2—N1—C1—S1168.40 (16)C5—C6—C7—C8179.46 (19)
C5—N2—C1—N1153.5 (2)C6—C7—C8—C90.7 (3)
C5—N2—C1—S130.4 (3)C7—C8—C9—C101.8 (3)
C1—N1—C2—C394.6 (2)C7—C8—C9—C12177.1 (2)
C4—N1—C2—C386.6 (2)C8—C9—C10—C111.4 (3)
N1—C2—C3—O166.9 (2)C12—C9—C10—C11177.5 (2)
C1—N2—C5—O210.2 (4)C9—C10—C11—C60.1 (3)
C1—N2—C5—C6170.0 (2)C7—C6—C11—C101.2 (3)
O2—C5—C6—C111.1 (3)C5—C6—C11—C10179.9 (2)
N2—C5—C6—C11179.1 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C6–C11 ring.
D—H···AD—HH···AD···AD—H···A
N2—H2N···O10.87 (2)2.02 (2)2.838 (3)157 (2)
O1—H1O···O2i0.84 (2)1.95 (2)2.750 (2)160 (2)
C2—H2B···S1ii0.972.833.783 (3)167
C4—H4B···Cg1iii0.962.673.605 (3)164
C12—H12A···Cg1iv0.963.003.932 (3)164
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x1/2, y+3/2, z+1; (iii) x1, y+3/2, z+3/2; (iv) x, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C6–C11 ring.
D—H···AD—HH···AD···AD—H···A
N2—H2N···O10.869 (18)2.019 (17)2.838 (3)156.9 (19)
O1—H1O···O2i0.84 (2)1.95 (2)2.750 (2)160 (2)
C2—H2B···S1ii0.972.833.783 (3)167
C4—H4B···Cg1iii0.962.673.605 (3)164
C12—H12A···Cg1iv0.963.003.932 (3)164
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x1/2, y+3/2, z+1; (iii) x1, y+3/2, z+3/2; (iv) x, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC12H16N2O2S
Mr252.33
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)7.351 (3), 12.452 (4), 13.423 (5)
V3)1228.8 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.20 × 0.16 × 0.15
Data collection
DiffractometerBruker SMART APEX
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.951, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
7036, 2790, 2637
Rint0.031
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.073, 1.02
No. of reflections2790
No. of parameters162
No. of restraints2
Δρmax, Δρmin (e Å3)0.18, 0.25
Absolute structureFlack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Absolute structure parameter0.10 (4)

Computer programs: SMART (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

 

Footnotes

Additional correspondence author, e-mail: nadiahhalim@um.edu.my.

Acknowledgements

The authors thank Peruntukan Penyelidikan Pascasiswazah (PPP, University of Malaya; PV036-2011A) and the Exploratory Research Grant Scheme (ER008-2013A) for support.

References

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