Ethyl 4-[3-(2-methyl­benzo­yl)thio­ureido]benzoate

Saeed, A.; Rafique, H.; Mumtaz, A.; Bolte, M.

doi:10.1107/S160053680904183X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2774

https://doi.org/10.1107/S160053680904183X

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Ethyl 4-[3-(2-methylbenzoyl)thioureido]benzoate

Aamer Saeed,^a ^* Hummera Rafique,^a Amara Mumtaz ^a and Michael Bolte ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan., and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany.
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 20 September 2009; accepted 13 October 2009; online 17 October 2009)

The molecular conformation of the title compound, C₁₈H₁₈N₂O₃S, is stabilized by an intramolecular N—H⋯O hydrogen bond. The crystal packing shows centrosymmetric dimers connected by N—H⋯S hydrogen bonds. The terminal ethoxy substituents are statistically disordered [occupancy ratio 0.527 (5):0.473 (5)].

Related literature

For the use of thiourea derivatives in organic synthesis and analysis, see: Eynde & Watte (2003 ); Fu et al. (1999 ); Rashdan et al. (2006 ); Maryanoff et al. (1986 ); Wang et al.(2005 ); Saeed et al. (2008 ); Koch, (2001 ). For their bioactivity and pharmaceutical applications, see: Upadhyaya & Srivastava (1982 ); Ramadas et al. (1998 ); Blum & Hayes (1979 ); DeBeer et al. (1936 ). For related structures, see: Saeed & Flörke (2007a ,b ); Saeed et al. (2009 ).

Experimental

Crystal data

C₁₈H₁₈N₂O₃S
M_r = 342.40
Triclinic, $[P \overline 1]$
a = 7.4555 (3) Å
b = 7.6311 (4) Å
c = 15.2468 (8) Å
α = 96.456 (4)°
β = 103.860 (5)°
γ = 92.908 (4)°
V = 834.13 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.33 × 0.32 × 0.28 mm

Data collection

Stoe IPDS II two-circle-diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009 ; Blessing, 1995 ) T_min = 0.933, T_max = 0.943
22798 measured reflections
4659 independent reflections
4311 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.100
S = 1.04
4659 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.80	2.01	2.669 (1)	139
N2—H2⋯S1ⁱ	0.89	2.67	3.5551 (9)	170
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680904183X/im2145sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680904183X/im2145Isup2.hkl

checkCIF report

Comment top

The background of this study has been described in our earlier paper concerning the crystal structure of 1-(2-Chloro-5-nitrophenyl)-3-(2,2-dimethylpropionyl)thiourea (Saeed et al., 2009). As part of our work on the structure of thioureas, we report here the structure of the title derivative, I, Fig 1.

The molecular conformation of the title compound, C₁₈H₁₈N₂O₃S, is stabilized by intramolecular N—H···O hydrogen bonds. The crystal packing shows centrosymmetric dimers connected by N—H···S hydrogen bonds (Table 1). Terminal ethoxy substituents are statistically disordered.

Related literature top

For the use of thiourea derivatives in organic synthesis and analysis, see: Eynde & Watte (2003); Fu et al. (1999); Rashdan et al. (2006); Maryanoff et al. (1986); Wang et al.(2005); Saeed et al. (2008); Koch, (2001). For their bioactivity and pharmaceutical applications, see: Upadhyaya & Srivastava (1982); Ramadas et al. (1998); Blum & Hayes (1979); DeBeer et al. (1936). For related structures, see: Saeed & Flörke (2007a,b); Saeed et al. (2009).

Experimental top

A solution of 2-methylbenzoyl chloride (10 mmol) in acetone (50 ml) was added dropwise to a suspension of potassium thiocyanate (10 mmol) in acetone (30 ml) and the reaction mixture was refluxed for 30 min. After cooling to room temperature, a solution of 4-aminobenzoic acid ethyl ester (10 mmol) in acetone (10 ml) was added and the resulting mixture refluxed for 3 h. The reaction mixture was poured into cold water and the precipitated thiourea was recrystallized from aqueous ethanol. Anal. calcd. for C₁₈H₁₈N₂O₃S: C, 63.14; H, 5.30; N, 8.18; S, 9.36% found: C, 63.26; H, 5.34; N, 8.21; S, 9.27%;

Structure description top

For the use of thiourea derivatives in organic synthesis and analysis, see: Eynde & Watte (2003); Fu et al. (1999); Rashdan et al. (2006); Maryanoff et al. (1986); Wang et al.(2005); Saeed et al. (2008); Koch, (2001). For their bioactivity and pharmaceutical applications, see: Upadhyaya & Srivastava (1982); Ramadas et al. (1998); Blum & Hayes (1979); DeBeer et al. (1936). For related structures, see: Saeed & Flörke (2007a,b); Saeed et al. (2009).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the title compound. The disordered atoms of the minor occupied site have been omitted for clarity. Displacement ellipsoids are shown at the 50 % probability level.
	Fig. 2. Packing diagram of the title compound. Hydrogen bonds shown as dashed lines. The minor occupied sites are omitted for clarity.

Ethyl 4-[3-(2-methylbenzoyl)thioureido]benzoate top

Crystal data top

C₁₈H₁₈N₂O₃S	Z = 2
M_r = 342.40	F(000) = 360
Triclinic, P1	D_x = 1.363 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4555 (3) Å	Cell parameters from 42517 reflections
b = 7.6311 (4) Å	θ = 3.4–29.9°
c = 15.2468 (8) Å	µ = 0.21 mm⁻¹
α = 96.456 (4)°	T = 173 K
β = 103.860 (5)°	Block, colourless
γ = 92.908 (4)°	0.33 × 0.32 × 0.28 mm
V = 834.13 (7) Å³

Data collection top

Stoe IPDS II two-circle- diffractometer	4659 independent reflections
Radiation source: fine-focus sealed tube	4311 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ω scans	θ_max = 29.6°, θ_min = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −10→10
T_min = 0.933, T_max = 0.943	k = −10→10
22798 measured reflections	l = −21→21

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) = 0.100	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0517P)² + 0.2098P] where P = (F_o² + 2F_c²)/3
4659 reflections	(Δ/σ)_max = 0.002
246 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₈H₁₈N₂O₃S	γ = 92.908 (4)°
M_r = 342.40	V = 834.13 (7) Å³
Triclinic, P1	Z = 2
a = 7.4555 (3) Å	Mo Kα radiation
b = 7.6311 (4) Å	µ = 0.21 mm⁻¹
c = 15.2468 (8) Å	T = 173 K
α = 96.456 (4)°	0.33 × 0.32 × 0.28 mm
β = 103.860 (5)°

Data collection top

Stoe IPDS II two-circle- diffractometer	4659 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	4311 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.943	R_int = 0.057
22798 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.04	Δρ_max = 0.28 e Å⁻³
4659 reflections	Δρ_min = −0.37 e Å⁻³
246 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.

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	Occ. (<1)
S1	1.09603 (4)	0.22920 (4)	0.599200 (16)	0.02926 (8)
O1	0.54635 (11)	0.37544 (11)	0.42973 (5)	0.03282 (18)
O2	1.1748 (4)	1.1151 (2)	0.86115 (13)	0.0302 (5)	0.527 (5)
O2A	1.0912 (4)	1.1206 (2)	0.88161 (14)	0.0309 (6)	0.473 (5)
O3	1.23261 (17)	0.91072 (12)	0.96012 (6)	0.0521 (3)
N1	0.82261 (12)	0.44800 (11)	0.57980 (5)	0.02358 (17)
H1	0.7282	0.4728	0.5478	0.028*
N2	0.77873 (12)	0.19546 (11)	0.47488 (6)	0.02420 (17)
H2	0.8242	0.0956	0.4570	0.029*
C1	0.89035 (13)	0.29850 (13)	0.55169 (6)	0.02227 (18)
C2	0.61524 (13)	0.23496 (13)	0.41838 (6)	0.02368 (18)
C11	0.90732 (12)	0.57062 (12)	0.65792 (6)	0.02124 (17)
C12	0.98398 (14)	0.51635 (13)	0.74226 (7)	0.02457 (19)
H12	0.9840	0.3941	0.7490	0.029*
C13	1.06022 (14)	0.64342 (13)	0.81625 (7)	0.02587 (19)
H13	1.1131	0.6075	0.8739	0.031*
C14	1.06025 (15)	0.82288 (13)	0.80705 (7)	0.0273 (2)
C15	0.97895 (15)	0.87601 (13)	0.72331 (7)	0.0286 (2)
H15	0.9755	0.9983	0.7170	0.034*
C16	0.90262 (14)	0.74958 (13)	0.64881 (6)	0.02458 (19)
H16	0.8471	0.7856	0.5915	0.029*
C17	1.1522 (2)	0.95152 (16)	0.88788 (9)	0.0456 (3)
C18	1.2785 (4)	1.2514 (3)	0.93166 (16)	0.0336 (6)	0.527 (5)
H18A	1.3222	1.3504	0.9033	0.040*	0.527 (5)
H18B	1.3886	1.2024	0.9681	0.040*	0.527 (5)
C19	1.1602 (4)	1.3183 (4)	0.9924 (2)	0.0404 (6)	0.527 (5)
H19A	1.2319	1.4107	1.0394	0.061*	0.527 (5)
H19B	1.1193	1.2206	1.0215	0.061*	0.527 (5)
H19C	1.0518	1.3673	0.9564	0.061*	0.527 (5)
C18A	1.1603 (4)	1.2562 (4)	0.9587 (2)	0.0324 (6)	0.473 (5)
H18C	1.1639	1.2048	1.0158	0.039*	0.473 (5)
H18D	1.0751	1.3519	0.9553	0.039*	0.473 (5)
C19A	1.3507 (5)	1.3318 (4)	0.9602 (2)	0.0419 (8)	0.473 (5)
H19D	1.3942	1.4226	1.0131	0.063*	0.473 (5)
H19E	1.3469	1.3849	0.9043	0.063*	0.473 (5)
H19F	1.4356	1.2375	0.9644	0.063*	0.473 (5)
C21	0.53091 (13)	0.08983 (13)	0.34332 (7)	0.02406 (19)
C22	0.50526 (15)	−0.08026 (14)	0.36571 (8)	0.0294 (2)
H22	0.5425	−0.1013	0.4275	0.035*
C23	0.42550 (17)	−0.21929 (16)	0.29831 (9)	0.0373 (3)
H23	0.4064	−0.3349	0.3136	0.045*
C24	0.37444 (18)	−0.18683 (18)	0.20872 (9)	0.0419 (3)
H24	0.3212	−0.2812	0.1621	0.050*
C25	0.40002 (17)	−0.01808 (17)	0.18616 (8)	0.0369 (3)
H25	0.3647	0.0011	0.1241	0.044*
C26	0.47678 (14)	0.12474 (15)	0.25293 (7)	0.0277 (2)
C27	0.49622 (18)	0.30658 (17)	0.22573 (8)	0.0363 (2)
H27A	0.3852	0.3678	0.2291	0.054*
H27B	0.5109	0.2969	0.1632	0.054*
H27C	0.6053	0.3737	0.2671	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02783 (13)	0.03461 (14)	0.02109 (12)	0.01339 (10)	−0.00154 (9)	−0.00282 (9)
O1	0.0292 (4)	0.0317 (4)	0.0296 (4)	0.0119 (3)	−0.0037 (3)	−0.0098 (3)
O2	0.0369 (11)	0.0226 (7)	0.0255 (8)	−0.0031 (6)	0.0009 (7)	−0.0036 (6)
O2A	0.0409 (14)	0.0227 (8)	0.0229 (8)	0.0024 (7)	−0.0005 (8)	−0.0048 (6)
O3	0.0761 (7)	0.0317 (4)	0.0293 (4)	−0.0019 (4)	−0.0204 (4)	−0.0010 (3)
N1	0.0232 (4)	0.0242 (4)	0.0187 (3)	0.0062 (3)	−0.0018 (3)	−0.0032 (3)
N2	0.0249 (4)	0.0245 (4)	0.0195 (4)	0.0070 (3)	0.0007 (3)	−0.0045 (3)
C1	0.0242 (4)	0.0250 (4)	0.0161 (4)	0.0044 (3)	0.0029 (3)	−0.0004 (3)
C2	0.0224 (4)	0.0264 (4)	0.0199 (4)	0.0046 (3)	0.0031 (3)	−0.0032 (3)
C11	0.0198 (4)	0.0235 (4)	0.0180 (4)	0.0019 (3)	0.0021 (3)	−0.0020 (3)
C12	0.0290 (4)	0.0217 (4)	0.0205 (4)	0.0023 (3)	0.0022 (3)	0.0007 (3)
C13	0.0305 (5)	0.0248 (4)	0.0188 (4)	0.0020 (4)	−0.0003 (3)	0.0017 (3)
C14	0.0304 (5)	0.0234 (4)	0.0219 (4)	−0.0016 (4)	−0.0035 (4)	−0.0004 (3)
C15	0.0337 (5)	0.0215 (4)	0.0252 (5)	−0.0009 (4)	−0.0020 (4)	0.0024 (3)
C16	0.0262 (4)	0.0253 (4)	0.0193 (4)	0.0023 (3)	0.0002 (3)	0.0025 (3)
C17	0.0634 (8)	0.0239 (5)	0.0322 (6)	−0.0038 (5)	−0.0185 (6)	−0.0001 (4)
C18	0.0361 (12)	0.0261 (11)	0.0317 (11)	−0.0045 (10)	0.0014 (9)	−0.0073 (9)
C19	0.0509 (14)	0.0331 (13)	0.0341 (14)	0.0081 (11)	0.0081 (11)	−0.0053 (11)
C18A	0.0436 (14)	0.0228 (12)	0.0262 (13)	0.0009 (10)	0.0060 (10)	−0.0101 (10)
C19A	0.0430 (15)	0.0352 (15)	0.0415 (15)	−0.0034 (13)	0.0032 (12)	−0.0028 (12)
C21	0.0200 (4)	0.0269 (4)	0.0222 (4)	0.0034 (3)	0.0035 (3)	−0.0065 (3)
C22	0.0272 (5)	0.0292 (5)	0.0310 (5)	0.0026 (4)	0.0085 (4)	−0.0031 (4)
C23	0.0334 (5)	0.0283 (5)	0.0479 (7)	−0.0032 (4)	0.0129 (5)	−0.0090 (5)
C24	0.0357 (6)	0.0405 (6)	0.0406 (6)	−0.0035 (5)	0.0054 (5)	−0.0208 (5)
C25	0.0342 (5)	0.0455 (6)	0.0244 (5)	0.0044 (5)	0.0018 (4)	−0.0121 (4)
C26	0.0243 (4)	0.0336 (5)	0.0222 (4)	0.0049 (4)	0.0036 (3)	−0.0053 (4)
C27	0.0398 (6)	0.0395 (6)	0.0283 (5)	0.0073 (5)	0.0056 (4)	0.0034 (4)

Geometric parameters (Å, º) top

S1—C1	1.6709 (10)	C18—H18A	0.9900
O1—C2	1.2247 (12)	C18—H18B	0.9900
O2—C17	1.370 (2)	C19—H19A	0.9800
O2—C18	1.451 (3)	C19—H19B	0.9800
O2A—C17	1.395 (2)	C19—H19C	0.9800
O2A—C18A	1.449 (4)	C18A—C19A	1.499 (4)
O3—C17	1.2038 (15)	C18A—H18C	0.9900
N1—C1	1.3388 (12)	C18A—H18D	0.9900
N1—C11	1.4220 (11)	C19A—H19D	0.9800
N1—H1	0.7998	C19A—H19E	0.9800
N2—C2	1.3824 (12)	C19A—H19F	0.9800
N2—C1	1.3936 (12)	C21—C22	1.3941 (15)
N2—H2	0.8911	C21—C26	1.4001 (14)
C2—C21	1.4937 (13)	C22—C23	1.3904 (15)
C11—C16	1.3895 (13)	C22—H22	0.9500
C11—C12	1.3941 (13)	C23—C24	1.382 (2)
C12—C13	1.3881 (13)	C23—H23	0.9500
C12—H12	0.9500	C24—C25	1.385 (2)
C13—C14	1.3923 (14)	C24—H24	0.9500
C13—H13	0.9500	C25—C26	1.4000 (14)
C14—C15	1.3900 (14)	C25—H25	0.9500
C14—C17	1.4858 (14)	C26—C27	1.5021 (17)
C15—C16	1.3904 (13)	C27—H27A	0.9800
C15—H15	0.9500	C27—H27B	0.9800
C16—H16	0.9500	C27—H27C	0.9800
C18—C19	1.493 (4)

C17—O2—C18	115.67 (16)	C18—C19—H19A	109.5
C17—O2A—C18A	118.32 (17)	C18—C19—H19B	109.5
C1—N1—C11	126.33 (8)	H19A—C19—H19B	109.5
C1—N1—H1	116.3	C18—C19—H19C	109.5
C11—N1—H1	117.2	H19A—C19—H19C	109.5
C2—N2—C1	128.53 (8)	H19B—C19—H19C	109.5
C2—N2—H2	115.7	O2A—C18A—C19A	111.2 (4)
C1—N2—H2	115.5	O2A—C18A—H18C	109.4
N1—C1—N2	116.03 (8)	C19A—C18A—H18C	109.4
N1—C1—S1	125.74 (7)	O2A—C18A—H18D	109.4
N2—C1—S1	118.21 (7)	C19A—C18A—H18D	109.4
O1—C2—N2	122.79 (9)	H18C—C18A—H18D	108.0
O1—C2—C21	123.60 (9)	C18A—C19A—H19D	109.5
N2—C2—C21	113.61 (8)	C18A—C19A—H19E	109.5
C16—C11—C12	120.35 (8)	H19D—C19A—H19E	109.5
C16—C11—N1	117.45 (8)	C18A—C19A—H19F	109.5
C12—C11—N1	122.11 (9)	H19D—C19A—H19F	109.5
C13—C12—C11	119.08 (9)	H19E—C19A—H19F	109.5
C13—C12—H12	120.5	C22—C21—C26	120.98 (9)
C11—C12—H12	120.5	C22—C21—C2	118.37 (9)
C12—C13—C14	120.85 (9)	C26—C21—C2	120.65 (9)
C12—C13—H13	119.6	C23—C22—C21	120.47 (11)
C14—C13—H13	119.6	C23—C22—H22	119.8
C15—C14—C13	119.70 (9)	C21—C22—H22	119.8
C15—C14—C17	122.23 (10)	C24—C23—C22	119.01 (12)
C13—C14—C17	118.05 (9)	C24—C23—H23	120.5
C14—C15—C16	119.80 (9)	C22—C23—H23	120.5
C14—C15—H15	120.1	C23—C24—C25	120.70 (10)
C16—C15—H15	120.1	C23—C24—H24	119.7
C11—C16—C15	120.18 (9)	C25—C24—H24	119.7
C11—C16—H16	119.9	C24—C25—C26	121.39 (11)
C15—C16—H16	119.9	C24—C25—H25	119.3
O3—C17—O2	124.17 (12)	C26—C25—H25	119.3
O3—C17—O2A	120.61 (13)	C25—C26—C21	117.44 (11)
O3—C17—C14	124.28 (11)	C25—C26—C27	119.59 (10)
O2—C17—C14	109.38 (11)	C21—C26—C27	122.97 (9)
O2A—C17—C14	112.60 (11)	C26—C27—H27A	109.5
O2—C18—C19	110.5 (3)	C26—C27—H27B	109.5
O2—C18—H18A	109.6	H27A—C27—H27B	109.5
C19—C18—H18A	109.6	C26—C27—H27C	109.5
O2—C18—H18B	109.6	H27A—C27—H27C	109.5
C19—C18—H18B	109.6	H27B—C27—H27C	109.5
H18A—C18—H18B	108.1

C11—N1—C1—N2	177.55 (9)	C15—C14—C17—O3	−175.89 (16)
C11—N1—C1—S1	−3.80 (15)	C13—C14—C17—O3	2.8 (2)
C2—N2—C1—N1	6.94 (15)	C15—C14—C17—O2	−12.1 (2)
C2—N2—C1—S1	−171.82 (9)	C13—C14—C17—O2	166.59 (17)
C1—N2—C2—O1	0.83 (17)	C15—C14—C17—O2A	22.0 (2)
C1—N2—C2—C21	−178.64 (9)	C13—C14—C17—O2A	−159.3 (2)
C1—N1—C11—C16	137.72 (11)	C17—O2—C18—C19	−77.4 (3)
C1—N1—C11—C12	−45.70 (15)	C17—O2A—C18A—C19A	79.8 (3)
C16—C11—C12—C13	−1.85 (15)	O1—C2—C21—C22	−128.25 (12)
N1—C11—C12—C13	−178.34 (9)	N2—C2—C21—C22	51.21 (12)
C11—C12—C13—C14	0.19 (16)	O1—C2—C21—C26	50.88 (15)
C12—C13—C14—C15	1.59 (17)	N2—C2—C21—C26	−129.66 (10)
C12—C13—C14—C17	−177.10 (12)	C26—C21—C22—C23	0.19 (16)
C13—C14—C15—C16	−1.71 (17)	C2—C21—C22—C23	179.32 (9)
C17—C14—C15—C16	176.93 (12)	C21—C22—C23—C24	0.89 (17)
C12—C11—C16—C15	1.74 (15)	C22—C23—C24—C25	−0.76 (19)
N1—C11—C16—C15	178.39 (9)	C23—C24—C25—C26	−0.44 (19)
C14—C15—C16—C11	0.06 (17)	C24—C25—C26—C21	1.48 (17)
C18—O2—C17—O3	−10.6 (4)	C24—C25—C26—C27	−177.99 (11)
C18—O2—C17—O2A	83.6 (3)	C22—C21—C26—C25	−1.35 (15)
C18—O2—C17—C14	−174.5 (2)	C2—C21—C26—C25	179.54 (9)
C18A—O2A—C17—O3	13.0 (4)	C22—C21—C26—C27	178.11 (10)
C18A—O2A—C17—O2	−93.5 (4)	C2—C21—C26—C27	−1.00 (15)
C18A—O2A—C17—C14	175.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.80	2.01	2.669 (1)	139
N2—H2···S1ⁱ	0.89	2.67	3.5551 (9)	170

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₂O₃S
M_r	342.40
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.4555 (3), 7.6311 (4), 15.2468 (8)
α, β, γ (°)	96.456 (4), 103.860 (5), 92.908 (4)
V (Å³)	834.13 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.33 × 0.32 × 0.28

Data collection
Diffractometer	Stoe IPDS II two-circle- diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.933, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	22798, 4659, 4311
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.695

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.04
No. of reflections	4659
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.37

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.80	2.01	2.669 (1)	138.9
N2—H2···S1ⁱ	0.89	2.67	3.5551 (9)	170.4

Symmetry code: (i) −x+2, −y, −z+1.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Blum, J. J. & Hayes, A. (1979). J. Supramol. Struct. 12, 23–34. CrossRef PubMed CAS Web of Science Google Scholar
DeBeer, E. J., Buck, J. S., Ide, W. S. & Hjort, A. M. (1936). J. Pharmacol. 57, 19–33. CAS Google Scholar
Eynde, J. J. V. & Watte, O. (2003). Arkivoc, iv, 93–101. CrossRef Google Scholar
Fu, M., Fernandez, M., Smith, M. L. & Flygae, J. A. (1999). Org. Lett. 1, 1351–1353. Web of Science CrossRef CAS Google Scholar
Koch, K. R. (2001). Coord. Chem. Rev. 216–217, 473–488. Web of Science CrossRef CAS Google Scholar
Maryanoff, C. A., Stanzione, R. C., Plampin, J. N. & Mills, J. E. (1986). J. Org. Chem. 51, 1882–1884. CrossRef CAS Web of Science Google Scholar
Ramadas, K., Suresh, G., Janarthanan, N. & Masilamani, S. (1998). Pestic. Sci. 52, 145–151. CrossRef CAS Google Scholar
Rashdan, S., Light, M. E. & Kilburn, J. D. (2006). Chem. Commun. pp. 4578–4580. Web of Science CSD CrossRef Google Scholar
Saeed, A. & Flörke, U. (2007a). Acta Cryst. E63, o4259. Web of Science CSD CrossRef IUCr Journals Google Scholar
Saeed, A. & Flörke, U. (2007b). Acta Cryst. E63, o4614. Web of Science CSD CrossRef IUCr Journals Google Scholar
Saeed, A., Khera, R. A., Simpson, J. & Stanley, R. G. (2009). Acta Cryst. E65, o1735–o1736. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Saeed, A., Zaman, S. & Bolte, M. (2008). Synth. Commun. 38, 2185–2199. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Upadhyaya, J. S. & Srivastava, P. K. (1982). J. Indian Chem. Soc. 59, 767–769. CAS Google Scholar
Wang, X.-C., Wang, F., Quan, Z.-J., Wang, M.-G. & Li, Z. (2005). J. Chem. Res. 61, 689–690. CrossRef Google Scholar

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