Ethyl 4-(3-butyrylthio­ureido)benzoate

Saeed, S.; Bhatti, M.H.; Tahir, M.K.; Jones, P.G.

doi:10.1107/S1600536808017868

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1369

doi:10.1107/S1600536808017868

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Ethyl 4-(3-butyrylthioureido)benzoate

Sohail Saeed,^a ^* Moazzam Hussain Bhatti,^a Muhammad Kalim Tahir ^a and Peter G. Jones ^b

^aDepartment of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan, and ^bInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany
^*Correspondence e-mail: sohail262001@yahoo.com

(Received 4 June 2008; accepted 12 June 2008; online 28 June 2008)

The title compound, C₁₄H₁₈N₂O₃S, crystallizes in the thioamide form with an intramolecular N—H⋯O hydrogen bond associated with the thiourea unit. With the benzoic acid and the butyrylthioureido units, the molecule consists of two planar building blocks connected by the common NH function adjacent to the aromatic ring. The interplanar angle is 33.38 (3)°. Molecules are connected in chains parallel to [110] by classical hydrogen bonds of the N—H⋯O type from the other NH group to the benzoate C=O of a neighboring molecule.

Related literature

For related literature, see: del Campo et al. (2002 ); D'hooghe et al. (2005 ); Dušek (1985 ); Huebner et al. (1953 ); Rodriguez-Fernandez et al. (2005 ); Xu et al. (2004 ); Zeng et al. (2003 ).

Experimental

Crystal data

C₁₄H₁₈N₂O₃S
M_r = 294.36
Triclinic, $[P \overline 1]$
a = 7.9817 (4) Å
b = 9.8843 (6) Å
c = 11.0759 (6) Å
α = 114.472 (6)°
β = 101.156 (4)°
γ = 102.277 (5)°
V = 737.15 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 100 (2) K
0.28 × 0.18 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur S diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.944, T_max = 1.000 (expected range = 0.918–0.973)
15025 measured reflections
4104 independent reflections
3045 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.096
S = 0.96
4104 reflections
191 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H02⋯O1	0.82 (2)	1.92 (2)	2.653 (1)	148 (2)
N1—H01⋯O2ⁱ	0.79 (1)	2.20 (1)	2.957 (1)	160 (2)
C13—H13A⋯O1ⁱⁱ	0.99	2.58	3.363 (2)	136
C1—H1B⋯Sⁱⁱⁱ	0.98	3.00	3.854 (2)	147
C13—H13B⋯S^iv	0.99	2.96	3.577 (1)	122
C14—H14C⋯S^v	0.98	2.98	3.821 (2)	144
Symmetry codes: (i) x-1, y-1, z; (ii) -x+1, -y+2, -z+1; (iii) x-1, y-1, z-1; (iv) x+1, y+1, z; (v) -x+2, -y+2, -z+2.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017868/im2072sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017868/im2072Isup2.hkl

checkCIF report

Comment top

Epoxy resins have the combination of good thermal and dimensional stability, excellent chemical and corrosion resistance, high tensile strength and modulus, and ease of handling and processability, ensuring their wide application in the aerospace and electronic industries in the form of structural adhesives, advanced composite matrices, and packaging materials (Dušek, 1985). The properties of cured epoxy polymers largely depend on the nature of chemical structure of the starting resins and curing agents. The title compound (I) is a precursor in an attempt to synthesize imidazole derivatives and transition metal complexes as epoxy resin curing agents and accelerators. Substituted thioureas are an important class of compounds, precursors or intermediates towards the synthesis of a variety of heterocyclic systems such as imidazole-2-thiones (Zeng et al., 2003), 2-imino-1,3-thiazolines (D'hooghe et al., 2005), pyrimidine-2-thiones and (benzothiazolyl)-4-quinazolinones. Thioureas are also known to exhibit a wide range of biological activities including antiviral, antibacterial, antifungal, antitubercular, antithyroidal, herbicidal and insecticidal activities (Huebner et al., 1953) and as agrochemicals (Xu et al., 2004). Among thiourea derivatives, acylthioureas, with O and S as potential donor sites, have been found to display a remarkably rich coordination chemistry. Such coordination compounds of thiourea have been studied for various biological systems (Rodriguez-Fernandez et al., 2005). In recent years some attention has also been paid to the potential use of acylthioureas as highly selective reagents for the enrichment and separation of metal cations (del Campo et al.,2002).

The title compound crystallizes in the thioamide form with an intramolecular hydrogen bond N2—H02···O1. Bond lengths and angles (cf. Supplementary Material) may be regarded as normal. The molecule consists of two planar building blocks: the butyrylthioureido group (S, C1–5, O1, N1, N2) and the benzoic acid moiety (C6–14, N2, O2, O3). Mean deviations from planarity for these moieties are 0.12 and 0.13 Å, respectively, and the interplanar angle is 33.38 (3)°. Molecules are connected to give infinite chains parallel to [110] by classical hydrogen bonds N1—H01···O2. These are in turn connected to antiparallel chains by the weak hydrogen bonds C13—H13A···O1. Additionally, there are three C—H···S contacts that may be borderline weak H bonds (Table 1, Fig. 2).

Related literature top

For related literature, see: del Campo et al. (2002); D'hooghe et al. (2005); Dušek (1985); Huebner et al. (1953); Rodriguez-Fernandez et al. (2005); Xu et al. (2004); Zeng et al. (2003).

Experimental top

A mixture of ammonium thiocyanate (26 mmol) and butanoyl chloride (26 mmol) in anhydrous acetone (70 ml) was stirred for 35 min. Then p-aminobenzoic acid ethyl ester (26 mmol) was added dropwise and the reaction mixture was refluxed for 2 h. After cooling, the reaction mixture was poured in acidified cold water. The resulting light green solid was filtered and washed with cold acetone.The product was recrystallized from ethanol as light greenish crystals (3.62 g, 91%), m.p. 412 K.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound in the crystal. Ellipsoids represent 50% probability levels.
	Fig. 2. Packing diagram of I showing classical and "weak" H bonds as thick or thin dashed bonds respectively. The double chain pattern is apparent.

Ethyl 4-(3-butyrylthioureido)benzoate top

Crystal data top

C₁₄H₁₈N₂O₃S	Z = 2
M_r = 294.36	F(000) = 312
Triclinic, P1	D_x = 1.326 Mg m⁻³
Hall symbol: -P 1	Melting point: 412 K
a = 7.9817 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8843 (6) Å	Cell parameters from 7295 reflections
c = 11.0759 (6) Å	θ = 2.8–30.7°
α = 114.472 (6)°	µ = 0.23 mm⁻¹
β = 101.156 (4)°	T = 100 K
γ = 102.277 (5)°	Pyramid, colourless
V = 737.15 (7) Å³	0.28 × 0.18 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur S diffractometer	4104 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3045 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 16.1057 pixels mm^-1	θ_max = 30.8°, θ_min = 2.8°
ω scans	h = −10→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −14→13
T_min = 0.944, T_max = 1.000	l = −15→15
15025 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.059P)²] where P = (F_o² + 2F_c²)/3
4104 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.45 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₈N₂O₃S	γ = 102.277 (5)°
M_r = 294.36	V = 737.15 (7) Å³
Triclinic, P1	Z = 2
a = 7.9817 (4) Å	Mo Kα radiation
b = 9.8843 (6) Å	µ = 0.23 mm⁻¹
c = 11.0759 (6) Å	T = 100 K
α = 114.472 (6)°	0.28 × 0.18 × 0.12 mm
β = 101.156 (4)°

Data collection top

Oxford Diffraction Xcalibur S diffractometer	4104 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	3045 reflections with I > 2σ(I)
T_min = 0.944, T_max = 1.000	R_int = 0.036
15025 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.45 e Å⁻³
4104 reflections	Δρ_min = −0.24 e Å⁻³
191 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 7.3219 (0.0010) x + 3.9334 (0.0038) y + 4.1423 (0.0037) z = 2.1058 (0.0010)

* -0.1410 (0.0006) S * -0.1556 (0.0012) C1 * -0.0747 (0.0014) C2 * 0.1521 (0.0012) C3 * 0.1191 (0.0012) C4 * -0.0053 (0.0010) C5 * 0.0111 (0.0008) O1 * 0.2033 (0.0010) N1 * -0.1089 (0.0009) N2

Rms deviation of fitted atoms = 0.1249

- 6.2227 (0.0013) x + 7.6804 (0.0015) y - 1.8402 (0.0041) z = 2.0195 (0.0017)

Angle to previous plane (with approximate e.s.d.) = 33.38 (0.03)

* -0.0510 (0.0011) C6 * -0.1492 (0.0011) C7 * -0.0777 (0.0011) C8 * 0.0751 (0.0012) C9 * 0.1972 (0.0012) C10 * 0.1468 (0.0011) C11 * 0.0732 (0.0011) C12 * 0.0367 (0.0013) C13 * -0.2621 (0.0011) C14 * 0.0788 (0.0009) O2 * 0.0421 (0.0010) O3 * -0.1099 (0.0009) N2

Rms deviation of fitted atoms = 0.1266

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
S	0.47787 (5)	0.62325 (4)	0.72720 (3)	0.02040 (10)
O1	0.11708 (12)	0.45529 (11)	0.28568 (9)	0.0208 (2)
O2	1.03683 (13)	1.25923 (10)	0.60929 (9)	0.0217 (2)
O3	1.04639 (12)	1.31498 (10)	0.82958 (9)	0.0200 (2)
N1	0.20683 (14)	0.45249 (13)	0.49337 (11)	0.0164 (2)
H01	0.186 (2)	0.3993 (17)	0.5294 (16)	0.020 (4)*
N2	0.38248 (15)	0.68105 (13)	0.51142 (11)	0.0168 (2)
H02	0.318 (2)	0.6327 (19)	0.4292 (16)	0.034 (5)*
C1	−0.2318 (2)	−0.03015 (17)	0.08970 (15)	0.0334 (4)
H1A	−0.1512	−0.0873	0.1061	0.050*
H1B	−0.2954	−0.0787	−0.0107	0.050*
H1C	−0.3200	−0.0343	0.1396	0.050*
C2	−0.1213 (2)	0.14034 (17)	0.14262 (14)	0.0313 (3)
H2A	−0.0333	0.1442	0.0912	0.038*
H2B	−0.2027	0.1971	0.1238	0.038*
C3	−0.02144 (18)	0.22120 (15)	0.29715 (13)	0.0195 (3)
H3A	−0.1110	0.2245	0.3480	0.023*
H3B	0.0497	0.1574	0.3162	0.023*
C4	0.10397 (16)	0.38601 (15)	0.35434 (13)	0.0161 (3)
C5	0.35361 (16)	0.58945 (14)	0.57240 (12)	0.0152 (2)
C6	0.52972 (17)	0.81999 (14)	0.56141 (13)	0.0158 (2)
C7	0.60248 (17)	0.84283 (15)	0.46402 (13)	0.0177 (3)
H7	0.5545	0.7659	0.3681	0.021*
C8	0.74473 (18)	0.97773 (15)	0.50722 (13)	0.0174 (3)
H8	0.7932	0.9937	0.4405	0.021*
C9	0.81749 (17)	1.09026 (14)	0.64780 (13)	0.0162 (3)
C10	0.74195 (17)	1.06811 (14)	0.74442 (13)	0.0176 (3)
H10	0.7898	1.1453	0.8402	0.021*
C11	0.59726 (18)	0.93406 (15)	0.70161 (13)	0.0183 (3)
H11	0.5448	0.9203	0.7675	0.022*
C12	0.97646 (17)	1.22913 (14)	0.69088 (13)	0.0168 (3)
C13	1.20350 (18)	1.45409 (16)	0.88185 (14)	0.0237 (3)
H13A	1.1674	1.5352	0.8632	0.028*
H13B	1.2942	1.4265	0.8350	0.028*
C14	1.28094 (19)	1.51477 (17)	1.03564 (14)	0.0267 (3)
H14A	1.1882	1.5369	1.0802	0.040*
H14B	1.3836	1.6116	1.0751	0.040*
H14C	1.3218	1.4356	1.0525	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.02247 (18)	0.01856 (17)	0.01304 (16)	−0.00118 (13)	−0.00170 (12)	0.00807 (12)
O1	0.0212 (5)	0.0233 (5)	0.0159 (5)	0.0035 (4)	0.0012 (4)	0.0114 (4)
O2	0.0249 (5)	0.0201 (5)	0.0190 (5)	0.0014 (4)	0.0087 (4)	0.0103 (4)
O3	0.0195 (5)	0.0196 (5)	0.0147 (4)	−0.0025 (4)	0.0005 (4)	0.0091 (4)
N1	0.0176 (5)	0.0163 (5)	0.0118 (5)	0.0002 (4)	0.0020 (4)	0.0072 (4)
N2	0.0179 (5)	0.0166 (5)	0.0114 (5)	0.0007 (4)	0.0007 (4)	0.0069 (4)
C1	0.0376 (9)	0.0212 (7)	0.0205 (7)	0.0011 (6)	−0.0044 (6)	0.0010 (6)
C2	0.0431 (9)	0.0214 (7)	0.0159 (7)	0.0027 (6)	−0.0031 (6)	0.0059 (6)
C3	0.0197 (6)	0.0180 (6)	0.0138 (6)	0.0018 (5)	0.0023 (5)	0.0046 (5)
C4	0.0147 (6)	0.0193 (6)	0.0126 (6)	0.0058 (5)	0.0036 (5)	0.0062 (5)
C5	0.0153 (6)	0.0146 (6)	0.0138 (6)	0.0040 (5)	0.0046 (5)	0.0055 (5)
C6	0.0153 (6)	0.0149 (6)	0.0166 (6)	0.0032 (5)	0.0030 (5)	0.0085 (5)
C7	0.0218 (7)	0.0169 (6)	0.0128 (6)	0.0053 (5)	0.0041 (5)	0.0066 (5)
C8	0.0220 (6)	0.0178 (6)	0.0155 (6)	0.0063 (5)	0.0071 (5)	0.0102 (5)
C9	0.0174 (6)	0.0152 (6)	0.0169 (6)	0.0043 (5)	0.0045 (5)	0.0093 (5)
C10	0.0215 (6)	0.0159 (6)	0.0132 (6)	0.0043 (5)	0.0040 (5)	0.0065 (5)
C11	0.0215 (6)	0.0188 (6)	0.0157 (6)	0.0050 (5)	0.0073 (5)	0.0093 (5)
C12	0.0186 (6)	0.0165 (6)	0.0170 (6)	0.0063 (5)	0.0048 (5)	0.0096 (5)
C13	0.0192 (7)	0.0222 (7)	0.0232 (7)	−0.0037 (5)	−0.0011 (5)	0.0135 (6)
C14	0.0227 (7)	0.0281 (8)	0.0198 (7)	0.0003 (6)	0.0025 (5)	0.0086 (6)

Geometric parameters (Å, º) top

S—C5	1.6617 (13)	C13—C14	1.4939 (18)
O1—C4	1.2207 (15)	N1—H01	0.791 (13)
O2—C12	1.2114 (15)	N2—H02	0.823 (15)
O3—C12	1.3336 (15)	C1—H1A	0.9800
O3—C13	1.4576 (15)	C1—H1B	0.9800
N1—C5	1.3850 (16)	C1—H1C	0.9800
N1—C4	1.3856 (16)	C2—H2A	0.9900
N2—C5	1.3443 (16)	C2—H2B	0.9900
N2—C6	1.4161 (16)	C3—H3A	0.9900
C1—C2	1.520 (2)	C3—H3B	0.9900
C2—C3	1.5071 (18)	C7—H7	0.9500
C3—C4	1.5044 (17)	C8—H8	0.9500
C6—C11	1.3929 (17)	C10—H10	0.9500
C6—C7	1.3930 (17)	C11—H11	0.9500
C7—C8	1.3833 (17)	C13—H13A	0.9900
C8—C9	1.3926 (17)	C13—H13B	0.9900
C9—C10	1.3944 (17)	C14—H14A	0.9800
C9—C12	1.4846 (17)	C14—H14B	0.9800
C10—C11	1.3896 (17)	C14—H14C	0.9800

C12—O3—C13	116.02 (10)	C2—C1—H1C	109.5
C5—N1—C4	129.07 (11)	H1A—C1—H1C	109.5
C5—N2—C6	127.24 (11)	H1B—C1—H1C	109.5
C3—C2—C1	111.68 (12)	C3—C2—H2A	109.3
C4—C3—C2	114.61 (11)	C1—C2—H2A	109.3
O1—C4—N1	122.53 (12)	C3—C2—H2B	109.3
O1—C4—C3	123.91 (11)	C1—C2—H2B	109.3
N1—C4—C3	113.56 (11)	H2A—C2—H2B	107.9
N2—C5—N1	114.66 (11)	C4—C3—H3A	108.6
N2—C5—S	126.56 (9)	C2—C3—H3A	108.6
N1—C5—S	118.75 (9)	C4—C3—H3B	108.6
C11—C6—C7	120.20 (11)	C2—C3—H3B	108.6
C11—C6—N2	122.15 (11)	H3A—C3—H3B	107.6
C7—C6—N2	117.61 (11)	C8—C7—H7	120.1
C8—C7—C6	119.86 (11)	C6—C7—H7	120.1
C7—C8—C9	120.51 (11)	C7—C8—H8	119.7
C8—C9—C10	119.35 (12)	C9—C8—H8	119.7
C8—C9—C12	118.79 (11)	C11—C10—H10	119.7
C10—C9—C12	121.84 (11)	C9—C10—H10	119.7
C11—C10—C9	120.51 (12)	C10—C11—H11	120.2
C10—C11—C6	119.52 (11)	C6—C11—H11	120.2
O2—C12—O3	124.13 (12)	O3—C13—H13A	110.2
O2—C12—C9	123.78 (11)	C14—C13—H13A	110.2
O3—C12—C9	112.08 (10)	O3—C13—H13B	110.2
O3—C13—C14	107.33 (10)	C14—C13—H13B	110.2
C5—N1—H01	115.6 (11)	H13A—C13—H13B	108.5
C4—N1—H01	114.8 (11)	C13—C14—H14A	109.5
C5—N2—H02	109.4 (11)	C13—C14—H14B	109.5
C6—N2—H02	121.4 (11)	H14A—C14—H14B	109.5
C2—C1—H1A	109.5	C13—C14—H14C	109.5
C2—C1—H1B	109.5	H14A—C14—H14C	109.5
H1A—C1—H1B	109.5	H14B—C14—H14C	109.5

C1—C2—C3—C4	174.75 (13)	C7—C8—C9—C10	−1.97 (19)
C5—N1—C4—O1	−10.3 (2)	C7—C8—C9—C12	176.71 (11)
C5—N1—C4—C3	168.79 (12)	C8—C9—C10—C11	0.99 (19)
C2—C3—C4—O1	4.85 (19)	C12—C9—C10—C11	−177.65 (12)
C2—C3—C4—N1	−174.24 (12)	C9—C10—C11—C6	1.1 (2)
C6—N2—C5—N1	−174.22 (11)	C7—C6—C11—C10	−2.31 (19)
C6—N2—C5—S	4.13 (19)	N2—C6—C11—C10	−179.92 (12)
C4—N1—C5—N2	10.80 (19)	C13—O3—C12—O2	1.00 (18)
C4—N1—C5—S	−167.69 (10)	C13—O3—C12—C9	179.95 (10)
C5—N2—C6—C11	−42.44 (19)	C8—C9—C12—O2	7.60 (19)
C5—N2—C6—C7	139.90 (13)	C10—C9—C12—O2	−173.76 (13)
C11—C6—C7—C8	1.35 (19)	C8—C9—C12—O3	−171.36 (12)
N2—C6—C7—C8	179.06 (11)	C10—C9—C12—O3	7.28 (17)
C6—C7—C8—C9	0.81 (19)	C12—O3—C13—C14	−169.36 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H02···O1	0.82 (2)	1.92 (2)	2.653 (1)	148 (2)
N1—H01···O2ⁱ	0.79 (1)	2.20 (1)	2.957 (1)	160 (2)
C13—H13A···O1ⁱⁱ	0.99	2.58	3.363 (2)	136
C1—H1B···Sⁱⁱⁱ	0.98	3.00	3.854 (2)	147
C13—H13B···S^iv	0.99	2.96	3.577 (1)	122
C14—H14C···S^v	0.98	2.98	3.821 (2)	144

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈N₂O₃S
M_r	294.36
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.9817 (4), 9.8843 (6), 11.0759 (6)
α, β, γ (°)	114.472 (6), 101.156 (4), 102.277 (5)
V (Å³)	737.15 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.28 × 0.18 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur S diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.944, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15025, 4104, 3045
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.720

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.096, 0.96
No. of reflections	4104
No. of parameters	191
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.24

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1994).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H02···O1	0.82 (2)	1.92 (2)	2.653 (1)	148 (2)
N1—H01···O2ⁱ	0.79 (1)	2.20 (1)	2.957 (1)	160 (2)
C13—H13A···O1ⁱⁱ	0.99	2.58	3.363 (2)	136.0
C1—H1B···Sⁱⁱⁱ	0.98	3.00	3.854 (2)	146.5
C13—H13B···S^iv	0.99	2.96	3.577 (1)	121.6
C14—H14C···S^v	0.98	2.98	3.821 (2)	143.9

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

References

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Volume 64| Part 7| July 2008| Page o1369

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