organic compounds
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
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.
Keywords: crystal structure; hydrogen bonding; thiourea.
CCDC reference: 1443797
Structure description
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 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.
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 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) 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 .
details are summarized in Table 2
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Structural data
CCDC reference: 1443797
10.1107/S2414314615024578/vm4002sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314615024578/vm4002Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314615024578/vm4002Isup3.cml
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.
The carbon-bound H-atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and were included in the
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).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.
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 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.
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 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).
Data collection: SMART (Bruker, 2009); cell
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).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. | |
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. |
C12H16N2O2S | Dx = 1.364 Mg m−3 |
Mr = 252.33 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 2964 reflections |
a = 7.351 (3) Å | θ = 2.2–29.9° |
b = 12.452 (4) Å | µ = 0.26 mm−1 |
c = 13.423 (5) Å | T = 296 K |
V = 1228.8 (7) Å3 | Block, yellow |
Z = 4 | 0.20 × 0.16 × 0.15 mm |
F(000) = 536 |
Bruker SMART APEX diffractometer | 2790 independent reflections |
Radiation source: fine-focus sealed tube | 2637 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 27.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.951, Tmax = 0.963 | k = −16→16 |
7036 measured reflections | l = −17→10 |
Refinement on F2 | Hydrogen 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) = 0.073 | Δρmax = 0.18 e Å−3 |
S = 1.02 | Δρmin = −0.25 e Å−3 |
2790 reflections | Absolute structure: Flack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
162 parameters | Absolute structure parameter: 0.10 (4) |
2 restraints |
C12H16N2O2S | V = 1228.8 (7) Å3 |
Mr = 252.33 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.351 (3) Å | µ = 0.26 mm−1 |
b = 12.452 (4) Å | T = 296 K |
c = 13.423 (5) Å | 0.20 × 0.16 × 0.15 mm |
Bruker SMART APEX diffractometer | 2790 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2637 reflections with I > 2σ(I) |
Tmin = 0.951, Tmax = 0.963 | Rint = 0.031 |
7036 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 2 restraints |
wR(F2) = 0.073 | Δρmax = 0.18 e Å−3 |
S = 1.02 | Δρmin = −0.25 e Å−3 |
2790 reflections | Absolute structure: Flack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
162 parameters | Absolute structure parameter: 0.10 (4) |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 1.01508 (8) | 0.90725 (4) | 0.57485 (4) | 0.01773 (14) | |
O1 | 1.1122 (2) | 0.66072 (11) | 0.30188 (12) | 0.0179 (3) | |
H1O | 1.208 (3) | 0.6932 (19) | 0.3173 (19) | 0.027* | |
O2 | 0.8730 (2) | 0.68828 (12) | 0.65388 (11) | 0.0188 (3) | |
N1 | 0.9313 (2) | 0.85435 (14) | 0.38890 (14) | 0.0151 (4) | |
N2 | 0.9723 (3) | 0.71025 (12) | 0.49351 (13) | 0.0154 (4) | |
H2N | 1.007 (3) | 0.6768 (17) | 0.4400 (12) | 0.019* | |
C1 | 0.9672 (3) | 0.82250 (15) | 0.48229 (15) | 0.0143 (4) | |
C2 | 0.8567 (3) | 0.78372 (17) | 0.31094 (16) | 0.0170 (5) | |
H2A | 0.7743 | 0.8249 | 0.2694 | 0.020* | |
H2B | 0.7871 | 0.7268 | 0.3422 | 0.020* | |
C3 | 1.0032 (3) | 0.73413 (16) | 0.24575 (15) | 0.0183 (4) | |
H3B | 0.9468 | 0.6965 | 0.1905 | 0.022* | |
H3C | 1.0798 | 0.7904 | 0.2187 | 0.022* | |
C4 | 0.9624 (3) | 0.96612 (16) | 0.35912 (17) | 0.0190 (5) | |
H4A | 1.0689 | 0.9931 | 0.3921 | 0.028* | |
H4B | 0.8590 | 1.0089 | 0.3774 | 0.028* | |
H4C | 0.9797 | 0.9696 | 0.2883 | 0.028* | |
C5 | 0.9380 (3) | 0.65102 (16) | 0.57733 (17) | 0.0142 (4) | |
C6 | 0.9851 (3) | 0.53401 (15) | 0.57083 (16) | 0.0140 (4) | |
C7 | 1.0600 (3) | 0.48527 (17) | 0.48678 (16) | 0.0158 (4) | |
H7 | 1.0827 | 0.5258 | 0.4299 | 0.019* | |
C8 | 1.1007 (3) | 0.37630 (16) | 0.48775 (17) | 0.0172 (5) | |
H8 | 1.1518 | 0.3448 | 0.4315 | 0.021* | |
C9 | 1.0662 (3) | 0.31339 (16) | 0.57154 (18) | 0.0164 (4) | |
C10 | 0.9946 (3) | 0.36278 (16) | 0.65533 (16) | 0.0170 (4) | |
H10 | 0.9732 | 0.3224 | 0.7124 | 0.020* | |
C11 | 0.9544 (3) | 0.47186 (16) | 0.65537 (17) | 0.0161 (4) | |
H11 | 0.9066 | 0.5036 | 0.7124 | 0.019* | |
C12 | 1.1028 (3) | 0.19392 (16) | 0.56988 (19) | 0.0201 (5) | |
H12A | 1.2151 | 0.1804 | 0.5356 | 0.030* | |
H12B | 1.0053 | 0.1579 | 0.5360 | 0.030* | |
H12C | 1.1113 | 0.1676 | 0.6370 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0235 (3) | 0.0120 (2) | 0.0178 (3) | 0.0004 (2) | −0.0022 (3) | −0.00127 (19) |
O1 | 0.0193 (8) | 0.0168 (8) | 0.0176 (8) | −0.0015 (6) | −0.0009 (7) | 0.0000 (6) |
O2 | 0.0250 (8) | 0.0139 (7) | 0.0177 (8) | 0.0026 (6) | 0.0046 (7) | 0.0007 (6) |
N1 | 0.0182 (9) | 0.0122 (8) | 0.0148 (9) | 0.0000 (7) | −0.0014 (7) | 0.0019 (7) |
N2 | 0.0218 (10) | 0.0111 (7) | 0.0134 (8) | 0.0009 (7) | 0.0018 (8) | −0.0009 (6) |
C1 | 0.0124 (10) | 0.0130 (9) | 0.0175 (10) | 0.0009 (8) | 0.0014 (8) | 0.0008 (8) |
C2 | 0.0178 (10) | 0.0165 (10) | 0.0167 (12) | −0.0017 (8) | −0.0040 (9) | 0.0012 (8) |
C3 | 0.0242 (11) | 0.0165 (9) | 0.0142 (10) | −0.0019 (9) | −0.0018 (10) | 0.0014 (7) |
C4 | 0.0237 (12) | 0.0131 (9) | 0.0202 (11) | 0.0003 (9) | 0.0022 (10) | 0.0053 (8) |
C5 | 0.0132 (9) | 0.0131 (9) | 0.0163 (10) | 0.0006 (7) | −0.0016 (9) | −0.0003 (8) |
C6 | 0.0131 (9) | 0.0125 (8) | 0.0163 (10) | 0.0001 (8) | −0.0023 (10) | 0.0011 (7) |
C7 | 0.0184 (11) | 0.0159 (9) | 0.0132 (11) | −0.0026 (8) | −0.0009 (9) | 0.0014 (8) |
C8 | 0.0177 (11) | 0.0169 (10) | 0.0170 (12) | 0.0008 (8) | −0.0006 (9) | −0.0028 (8) |
C9 | 0.0136 (9) | 0.0122 (9) | 0.0234 (11) | −0.0003 (7) | −0.0043 (9) | −0.0013 (9) |
C10 | 0.0179 (10) | 0.0151 (9) | 0.0182 (10) | 0.0001 (9) | 0.0005 (10) | 0.0037 (8) |
C11 | 0.0165 (10) | 0.0167 (9) | 0.0150 (10) | 0.0003 (8) | 0.0017 (9) | −0.0014 (8) |
C12 | 0.0218 (11) | 0.0129 (9) | 0.0257 (12) | 0.0016 (8) | 0.0003 (10) | 0.0003 (10) |
S1—C1 | 1.668 (2) | C4—H4C | 0.9600 |
O1—C3 | 1.430 (3) | C5—C6 | 1.500 (3) |
O1—H1O | 0.838 (13) | C6—C11 | 1.392 (3) |
O2—C5 | 1.225 (3) | C6—C7 | 1.394 (3) |
N1—C1 | 1.341 (3) | C7—C8 | 1.390 (3) |
N1—C4 | 1.466 (3) | C7—H7 | 0.9300 |
N1—C2 | 1.473 (3) | C8—C9 | 1.394 (3) |
N2—C5 | 1.369 (3) | C8—H8 | 0.9300 |
N2—C1 | 1.406 (2) | C9—C10 | 1.386 (3) |
N2—H2N | 0.868 (12) | C9—C12 | 1.512 (3) |
C2—C3 | 1.518 (3) | C10—C11 | 1.390 (3) |
C2—H2A | 0.9700 | C10—H10 | 0.9300 |
C2—H2B | 0.9700 | C11—H11 | 0.9300 |
C3—H3B | 0.9700 | C12—H12A | 0.9600 |
C3—H3C | 0.9700 | C12—H12B | 0.9600 |
C4—H4A | 0.9600 | C12—H12C | 0.9600 |
C4—H4B | 0.9600 | ||
C3—O1—H1O | 107.1 (18) | O2—C5—N2 | 123.87 (18) |
C1—N1—C4 | 120.34 (18) | O2—C5—C6 | 120.45 (19) |
C1—N1—C2 | 124.11 (17) | N2—C5—C6 | 115.68 (18) |
C4—N1—C2 | 115.54 (17) | C11—C6—C7 | 118.79 (18) |
C5—N2—C1 | 128.23 (18) | C11—C6—C5 | 117.08 (19) |
C5—N2—H2N | 118.4 (15) | C7—C6—C5 | 124.11 (19) |
C1—N2—H2N | 113.3 (15) | C8—C7—C6 | 120.2 (2) |
N1—C1—N2 | 113.53 (18) | C8—C7—H7 | 119.9 |
N1—C1—S1 | 123.42 (15) | C6—C7—H7 | 119.9 |
N2—C1—S1 | 122.93 (15) | C7—C8—C9 | 121.1 (2) |
N1—C2—C3 | 112.86 (18) | C7—C8—H8 | 119.4 |
N1—C2—H2A | 109.0 | C9—C8—H8 | 119.4 |
C3—C2—H2A | 109.0 | C10—C9—C8 | 118.33 (19) |
N1—C2—H2B | 109.0 | C10—C9—C12 | 121.1 (2) |
C3—C2—H2B | 109.0 | C8—C9—C12 | 120.6 (2) |
H2A—C2—H2B | 107.8 | C9—C10—C11 | 121.0 (2) |
O1—C3—C2 | 110.70 (17) | C9—C10—H10 | 119.5 |
O1—C3—H3B | 109.5 | C11—C10—H10 | 119.5 |
C2—C3—H3B | 109.5 | C10—C11—C6 | 120.6 (2) |
O1—C3—H3C | 109.5 | C10—C11—H11 | 119.7 |
C2—C3—H3C | 109.5 | C6—C11—H11 | 119.7 |
H3B—C3—H3C | 108.1 | C9—C12—H12A | 109.5 |
N1—C4—H4A | 109.5 | C9—C12—H12B | 109.5 |
N1—C4—H4B | 109.5 | H12A—C12—H12B | 109.5 |
H4A—C4—H4B | 109.5 | C9—C12—H12C | 109.5 |
N1—C4—H4C | 109.5 | H12A—C12—H12C | 109.5 |
H4A—C4—H4C | 109.5 | H12B—C12—H12C | 109.5 |
H4B—C4—H4C | 109.5 | ||
C4—N1—C1—N2 | −165.77 (19) | O2—C5—C6—C7 | −179.8 (2) |
C2—N1—C1—N2 | 15.5 (3) | N2—C5—C6—C7 | 0.4 (3) |
C4—N1—C1—S1 | 10.3 (3) | C11—C6—C7—C8 | 0.8 (3) |
C2—N1—C1—S1 | −168.40 (16) | C5—C6—C7—C8 | 179.46 (19) |
C5—N2—C1—N1 | −153.5 (2) | C6—C7—C8—C9 | 0.7 (3) |
C5—N2—C1—S1 | 30.4 (3) | C7—C8—C9—C10 | −1.8 (3) |
C1—N1—C2—C3 | −94.6 (2) | C7—C8—C9—C12 | 177.1 (2) |
C4—N1—C2—C3 | 86.6 (2) | C8—C9—C10—C11 | 1.4 (3) |
N1—C2—C3—O1 | 66.9 (2) | C12—C9—C10—C11 | −177.5 (2) |
C1—N2—C5—O2 | 10.2 (4) | C9—C10—C11—C6 | 0.1 (3) |
C1—N2—C5—C6 | −170.0 (2) | C7—C6—C11—C10 | −1.2 (3) |
O2—C5—C6—C11 | −1.1 (3) | C5—C6—C11—C10 | −179.9 (2) |
N2—C5—C6—C11 | 179.1 (2) |
Cg1 is the centroid of the C6–C11 ring. |
D—H···A | D—H | H···A | D···A | 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—H4B···Cg1iii | 0.96 | 2.67 | 3.605 (3) | 164 |
C12—H12A···Cg1iv | 0.96 | 3.00 | 3.932 (3) | 164 |
Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x−1/2, −y+3/2, −z+1; (iii) −x−1, y+3/2, −z+3/2; (iv) −x, y+1/2, −z+3/2. |
Cg1 is the centroid of the C6–C11 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O1 | 0.869 (18) | 2.019 (17) | 2.838 (3) | 156.9 (19) |
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—H4B···Cg1iii | 0.96 | 2.67 | 3.605 (3) | 164 |
C12—H12A···Cg1iv | 0.96 | 3.00 | 3.932 (3) | 164 |
Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x−1/2, −y+3/2, −z+1; (iii) −x−1, y+3/2, −z+3/2; (iv) −x, y+1/2, −z+3/2. |
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) |
V (Å3) | 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 |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
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 (Å−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) |
Absolute structure parameter | 0.10 (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
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Rauf, M. K., Imtiaz-ud-Din, Badshah, A., Gielen, M., Ebihara, M., de Vos, D. & Ahmed, S. (2009). J. Inorg. Biochem. 103, 1135–1144. Web of Science CSD CrossRef PubMed CAS Google Scholar
Selvakumaran, N., Ng, S. W., Tiekink, E. R. T. & Karvembu, R. (2011). Inorg. Chim. Acta, 376, 278–284. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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
Yamin, B. M., Hizam, S. M. M., Yusoff, S. F. M. & Hasbullah, S. A. (2014). Acta Cryst. E70, o602. CSD CrossRef IUCr Journals Google Scholar
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