Mefenacet [2-(1,3-benzothia­zol-2-yl­oxy)-N-methyl-N-phenyl­acetamide]

Cheon, S.; Kim, T.H.; Moon, S.-H.; Kim, J.

doi:10.1107/S1600536810044284

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3153

https://doi.org/10.1107/S1600536810044284

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Mefenacet [2-(1,3-benzothiazol-2-yloxy)-N-methyl-N-phenylacetamide]

Sanghun Cheon,^a Tae Ho Kim,^a ^* Suk-Hee Moon ^b and Jineun Kim ^a ^*

^aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea, and ^bSubdivision of Food Science, Kyungnam College of Information and Technology, Busan 616-701, Republic of Korea
^*Correspondence e-mail: jekim@gnu.ac.kr, thkim@gnu.ac.kr

(Received 25 October 2010; accepted 29 October 2010; online 13 November 2010)

The title compound, C₁₆H₁₄N₂O₂S, crystallizes with two independent molecules in the asymmetric unit. The dihedral angles between the plane of the benzothiazole ring system and the phenyl ring plane are 51.63 (7) and 60.46 (5)°. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions contribute to the stabilization of the packing.

Related literature

For information on the toxicity and herbicidal properties of the title compound, see: Lu et al. (2001 ). For related structures, see: Murru et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₄N₂O₂S
M_r = 298.35
Monoclinic, P 2₁ /c
a = 11.2708 (6) Å
b = 15.7112 (9) Å
c = 19.9579 (8) Å
β = 122.997 (2)°
V = 2964.0 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.19 × 0.17 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.959, T_max = 0.980
30345 measured reflections
7338 independent reflections
5174 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.107
S = 1.02
7338 reflections
381 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg,1 Cg2 and Cg3 are the centroids of the C27–C32, C17–C22 and S1/C1/C6/N1/C7 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4ⁱ	0.95	2.44	3.273 (2)	147
C8—H8B⋯O3ⁱⁱ	0.99	2.43	3.235 (2)	138
C24—H24B⋯O2	0.99	2.35	3.256 (2)	153
C15—H15⋯Cg1ⁱⁱ	0.95	2.97	3.84	154
C26—H26B⋯Cg2ⁱⁱⁱ	0.98	3.00	3.74	134
C29—H29⋯Cg3^iv	0.95	2.95	3.74	141
C30—H30⋯Cg2ⁱ	0.95	2.80	3.42	124
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810044284/wn2417sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044284/wn2417Isup2.hkl

checkCIF report

Comment top

Mefenacet (systematic name: 2-(1,3-benzothiazol-2-yloxy)-N- methylacetanilide), is a type of herbicide with low toxicity and high activity (Lu et al. 2001). However its crystal structure has not hitherto been reported.

In the asymmetric unit (Fig. 1), the dihedral angles between the plane of the benzothiazole ring system and the phenyl ring plane are 51.63 (7)° and 60.46 (5)°. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structures (Murru et al., 2009).

In the crystal structure, as shown in Fig. 2, weak intermolecular C—H···O hydrogen bonds and C—H···π interactions are observed (Table 1). These intermolecular interactions may contribute to the stabilization of the packing.

Related literature top

For information on the toxicity and herbicidal properties of the title compound, see: Lu et al. (2001). For related crystal structures, see: Murru et al. (2009).

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH₂Cl₂ gave single crystals suitable for X-ray analysis.

Structure description top

For information on the toxicity and herbicidal properties of the title compound, see: Lu et al. (2001). For related crystal structures, see: Murru et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of the title compound, with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are represented by small spheres of arbitrary radius.

Fig. 2. Crystal packing of the title compound with intermolecular C—H···O and C—H···π interactions shown as dashed lines. H atoms not involved in intermolecular interactions have been omitted for clarity. Cg1—Cg3 are the centroids of the C27–C32, C17–C22, and S1/C1/C6/N1/C7 rings, respectively. [Symmetry codes: (i) x + 1, -y + 1.5, z + 1/2; (ii) -x +1, -y + 1, -z + 1; (iii) x, -y + 1.5, z - 1/2; (iv) -x + 1, y - 1/2, -z + 1/2; (v) -x + 1, y - 1/2, -z + 1.5; (vi) x, -y + 1.5, z + 1/2.)

2-(1,3-benzothiazol-2-yloxy)-N-methyl-N-phenylacetamide top

Crystal data top

C₁₆H₁₄N₂O₂S	F(000) = 1248
M_r = 298.35	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5175 reflections
a = 11.2708 (6) Å	θ = 2.2–25.3°
b = 15.7112 (9) Å	µ = 0.22 mm⁻¹
c = 19.9579 (8) Å	T = 173 K
β = 122.997 (2)°	Block, colourless
V = 2964.0 (3) Å³	0.19 × 0.17 × 0.09 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	7338 independent reflections
Radiation source: fine-focus sealed tube	5174 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
φ and ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.959, T_max = 0.980	k = −18→20
30345 measured reflections	l = −26→26

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0435P)² + 0.7531P] where P = (F_o² + 2F_c²)/3
7338 reflections	(Δ/σ)_max = 0.001
381 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₄N₂O₂S	V = 2964.0 (3) Å³
M_r = 298.35	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2708 (6) Å	µ = 0.22 mm⁻¹
b = 15.7112 (9) Å	T = 173 K
c = 19.9579 (8) Å	0.19 × 0.17 × 0.09 mm
β = 122.997 (2)°

Data collection top

Bruker APEXII CCD diffractometer	7338 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5174 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.980	R_int = 0.045
30345 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.02	Δρ_max = 0.27 e Å⁻³
7338 reflections	Δρ_min = −0.28 e Å⁻³
381 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.

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
S1	0.94569 (4)	0.65520 (3)	0.70419 (3)	0.03607 (12)
S2	0.21697 (5)	0.53839 (3)	0.15747 (3)	0.03835 (13)
O1	0.71887 (12)	0.56299 (8)	0.65599 (8)	0.0371 (3)
O2	0.53812 (13)	0.61502 (8)	0.50454 (8)	0.0407 (3)
O3	0.37291 (13)	0.62655 (7)	0.28811 (7)	0.0358 (3)
O4	0.30217 (13)	0.78901 (8)	0.29306 (9)	0.0462 (3)
N1	0.69842 (14)	0.70886 (9)	0.66837 (9)	0.0310 (3)
N2	0.34408 (15)	0.59934 (9)	0.51009 (9)	0.0344 (3)
N3	0.38648 (14)	0.66403 (9)	0.17928 (8)	0.0310 (3)
N4	0.52868 (15)	0.83502 (9)	0.36531 (10)	0.0402 (4)
C1	0.92417 (17)	0.76410 (11)	0.71071 (10)	0.0289 (4)
C2	1.02172 (17)	0.82906 (12)	0.73152 (10)	0.0338 (4)
H2	1.1156	0.8173	0.7462	0.041*
C3	0.97758 (19)	0.91139 (12)	0.73012 (11)	0.0366 (4)
H3	1.0418	0.9572	0.7434	0.044*
C4	0.84079 (19)	0.92827 (12)	0.70967 (11)	0.0376 (4)
H4	0.8133	0.9855	0.7096	0.045*
C5	0.74394 (18)	0.86369 (11)	0.68950 (11)	0.0356 (4)
H5	0.6508	0.8760	0.6759	0.043*
C6	0.78526 (17)	0.78025 (11)	0.68938 (10)	0.0285 (4)
C7	0.76859 (17)	0.64308 (11)	0.67289 (10)	0.0304 (4)
C8	0.57044 (18)	0.55577 (11)	0.62402 (11)	0.0349 (4)
H8A	0.5481	0.5861	0.6593	0.042*
H8B	0.5454	0.4950	0.6223	0.042*
C9	0.48359 (18)	0.59301 (10)	0.54072 (10)	0.0311 (4)
C10	0.2484 (2)	0.62796 (14)	0.42757 (11)	0.0465 (5)
H10A	0.3006	0.6636	0.4118	0.070*
H10B	0.1710	0.6610	0.4235	0.070*
H10C	0.2095	0.5784	0.3922	0.070*
C11	0.27959 (17)	0.56221 (11)	0.54862 (10)	0.0324 (4)
C12	0.2600 (2)	0.61034 (13)	0.59977 (12)	0.0417 (4)
H12	0.2915	0.6677	0.6111	0.050*
C13	0.1940 (2)	0.57392 (16)	0.63416 (13)	0.0555 (6)
H13	0.1807	0.6063	0.6698	0.067*
C14	0.1474 (2)	0.49112 (16)	0.61706 (14)	0.0575 (6)
H14	0.1009	0.4668	0.6404	0.069*
C15	0.1676 (2)	0.44331 (14)	0.56647 (14)	0.0540 (6)
H15	0.1361	0.3859	0.5553	0.065*
C16	0.2339 (2)	0.47876 (12)	0.53191 (12)	0.0423 (5)
H16	0.2481	0.4460	0.4968	0.051*
C17	0.23107 (18)	0.56733 (11)	0.07802 (11)	0.0351 (4)
C18	0.1640 (2)	0.53245 (13)	0.00209 (13)	0.0489 (5)
H18	0.1012	0.4856	−0.0126	0.059*
C19	0.1912 (2)	0.56794 (16)	−0.05143 (14)	0.0589 (6)
H19	0.1450	0.5458	−0.1041	0.071*
C20	0.2847 (3)	0.63537 (15)	−0.02975 (13)	0.0555 (6)
H20	0.3015	0.6584	−0.0679	0.067*
C21	0.3540 (2)	0.66979 (13)	0.04629 (12)	0.0431 (5)
H21	0.4188	0.7155	0.0610	0.052*
C22	0.32599 (18)	0.63536 (11)	0.10061 (11)	0.0323 (4)
C23	0.33790 (17)	0.61924 (10)	0.21272 (10)	0.0300 (4)
C24	0.48587 (18)	0.68520 (11)	0.33700 (11)	0.0337 (4)
H24A	0.5552	0.6842	0.3211	0.040*
H24B	0.5352	0.6675	0.3937	0.040*
C25	0.42889 (18)	0.77450 (11)	0.32799 (11)	0.0335 (4)
C26	0.4871 (2)	0.92358 (13)	0.36470 (17)	0.0638 (7)
H26A	0.4925	0.9557	0.3244	0.096*
H26B	0.5510	0.9490	0.4174	0.096*
H26C	0.3899	0.9252	0.3519	0.096*
C27	0.67722 (18)	0.81716 (11)	0.40232 (11)	0.0333 (4)
C28	0.73303 (19)	0.81424 (12)	0.35549 (12)	0.0387 (4)
H28	0.6737	0.8235	0.2995	0.046*
C29	0.87550 (19)	0.79774 (12)	0.39043 (12)	0.0416 (5)
H29	0.9141	0.7954	0.3584	0.050*
C30	0.9613 (2)	0.78468 (12)	0.47130 (13)	0.0432 (5)
H30	1.0592	0.7737	0.4953	0.052*
C31	0.9050 (2)	0.78758 (14)	0.51738 (13)	0.0495 (5)
H31	0.9646	0.7783	0.5733	0.059*
C32	0.7627 (2)	0.80379 (13)	0.48354 (12)	0.0455 (5)
H32	0.7245	0.8057	0.5158	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0286 (2)	0.0329 (2)	0.0472 (3)	0.00576 (18)	0.0210 (2)	0.0021 (2)
S2	0.0339 (2)	0.0301 (2)	0.0484 (3)	−0.00813 (18)	0.0207 (2)	−0.0074 (2)
O1	0.0329 (6)	0.0308 (6)	0.0433 (8)	−0.0001 (5)	0.0178 (6)	0.0011 (6)
O2	0.0446 (7)	0.0475 (8)	0.0369 (7)	−0.0051 (6)	0.0266 (6)	0.0006 (6)
O3	0.0383 (7)	0.0326 (7)	0.0316 (7)	−0.0099 (5)	0.0158 (6)	0.0015 (5)
O4	0.0305 (7)	0.0413 (8)	0.0622 (9)	−0.0038 (6)	0.0224 (7)	0.0042 (7)
N1	0.0274 (7)	0.0329 (8)	0.0328 (8)	0.0009 (6)	0.0166 (6)	−0.0005 (6)
N2	0.0366 (8)	0.0372 (8)	0.0296 (8)	0.0020 (6)	0.0182 (7)	0.0050 (6)
N3	0.0318 (7)	0.0276 (7)	0.0305 (8)	−0.0017 (6)	0.0150 (7)	0.0006 (6)
N4	0.0319 (8)	0.0315 (8)	0.0582 (11)	−0.0043 (6)	0.0251 (8)	−0.0048 (7)
C1	0.0275 (8)	0.0324 (9)	0.0260 (9)	0.0048 (7)	0.0141 (7)	0.0031 (7)
C2	0.0241 (8)	0.0420 (10)	0.0323 (10)	−0.0011 (7)	0.0134 (7)	−0.0003 (8)
C3	0.0364 (9)	0.0349 (10)	0.0366 (10)	−0.0042 (8)	0.0187 (8)	−0.0015 (8)
C4	0.0411 (10)	0.0322 (9)	0.0399 (11)	0.0034 (8)	0.0223 (9)	−0.0004 (8)
C5	0.0293 (9)	0.0365 (10)	0.0417 (11)	0.0053 (7)	0.0199 (8)	−0.0004 (8)
C6	0.0265 (8)	0.0328 (9)	0.0258 (9)	0.0027 (7)	0.0140 (7)	0.0006 (7)
C7	0.0278 (8)	0.0330 (9)	0.0295 (9)	−0.0002 (7)	0.0150 (7)	0.0007 (7)
C8	0.0327 (9)	0.0339 (10)	0.0350 (10)	−0.0049 (7)	0.0165 (8)	0.0027 (8)
C9	0.0384 (9)	0.0250 (8)	0.0311 (9)	−0.0031 (7)	0.0196 (8)	−0.0038 (7)
C10	0.0461 (11)	0.0539 (13)	0.0334 (11)	0.0082 (9)	0.0177 (9)	0.0084 (9)
C11	0.0283 (8)	0.0356 (9)	0.0315 (10)	0.0035 (7)	0.0151 (8)	0.0042 (7)
C12	0.0452 (11)	0.0407 (11)	0.0429 (11)	−0.0015 (9)	0.0264 (10)	−0.0051 (9)
C13	0.0553 (13)	0.0748 (16)	0.0501 (14)	−0.0038 (12)	0.0376 (12)	−0.0081 (12)
C14	0.0472 (12)	0.0788 (17)	0.0521 (14)	−0.0115 (12)	0.0306 (11)	0.0092 (12)
C15	0.0529 (13)	0.0469 (12)	0.0608 (15)	−0.0128 (10)	0.0300 (12)	0.0017 (11)
C16	0.0423 (11)	0.0399 (11)	0.0453 (12)	−0.0020 (8)	0.0241 (10)	−0.0051 (9)
C17	0.0275 (8)	0.0321 (9)	0.0388 (11)	0.0062 (7)	0.0135 (8)	−0.0040 (8)
C18	0.0395 (11)	0.0462 (12)	0.0494 (13)	0.0059 (9)	0.0168 (10)	−0.0157 (10)
C19	0.0596 (14)	0.0667 (15)	0.0420 (13)	0.0114 (12)	0.0223 (11)	−0.0172 (11)
C20	0.0678 (15)	0.0621 (15)	0.0446 (13)	0.0160 (12)	0.0358 (12)	0.0015 (11)
C21	0.0487 (11)	0.0435 (11)	0.0429 (12)	0.0087 (9)	0.0287 (10)	0.0040 (9)
C22	0.0307 (8)	0.0294 (9)	0.0328 (10)	0.0071 (7)	0.0147 (8)	0.0001 (7)
C23	0.0269 (8)	0.0242 (8)	0.0331 (10)	−0.0015 (6)	0.0125 (7)	0.0006 (7)
C24	0.0317 (9)	0.0327 (9)	0.0280 (9)	−0.0070 (7)	0.0107 (8)	0.0016 (7)
C25	0.0325 (9)	0.0352 (10)	0.0351 (10)	−0.0056 (7)	0.0199 (8)	0.0019 (8)
C26	0.0457 (12)	0.0342 (11)	0.114 (2)	−0.0049 (9)	0.0448 (14)	−0.0109 (12)
C27	0.0303 (9)	0.0295 (9)	0.0397 (11)	−0.0070 (7)	0.0187 (8)	−0.0045 (8)
C28	0.0376 (10)	0.0405 (10)	0.0360 (11)	−0.0051 (8)	0.0187 (9)	0.0042 (8)
C29	0.0371 (10)	0.0460 (11)	0.0475 (12)	−0.0053 (8)	0.0268 (10)	0.0003 (9)
C30	0.0320 (10)	0.0363 (10)	0.0516 (13)	−0.0067 (8)	0.0165 (9)	−0.0053 (9)
C31	0.0445 (11)	0.0561 (13)	0.0308 (11)	−0.0048 (10)	0.0095 (9)	−0.0039 (9)
C32	0.0510 (12)	0.0508 (12)	0.0408 (12)	−0.0065 (10)	0.0289 (10)	−0.0090 (9)

Geometric parameters (Å, º) top

S1—C1	1.7428 (17)	C11—C12	1.381 (3)
S1—C7	1.7472 (17)	C12—C13	1.382 (3)
S2—C17	1.738 (2)	C12—H12	0.9500
S2—C23	1.7465 (17)	C13—C14	1.375 (3)
O1—C7	1.344 (2)	C13—H13	0.9500
O1—C8	1.434 (2)	C14—C15	1.374 (3)
O2—C9	1.226 (2)	C14—H14	0.9500
O3—C23	1.336 (2)	C15—C16	1.380 (3)
O3—C24	1.438 (2)	C15—H15	0.9500
O4—C25	1.222 (2)	C16—H16	0.9500
N1—C7	1.274 (2)	C17—C18	1.386 (3)
N1—C6	1.395 (2)	C17—C22	1.402 (2)
N2—C9	1.345 (2)	C18—C19	1.380 (3)
N2—C11	1.438 (2)	C18—H18	0.9500
N2—C10	1.464 (2)	C19—C20	1.387 (3)
N3—C23	1.280 (2)	C19—H19	0.9500
N3—C22	1.403 (2)	C20—C21	1.384 (3)
N4—C25	1.346 (2)	C20—H20	0.9500
N4—C27	1.442 (2)	C21—C22	1.393 (3)
N4—C26	1.466 (2)	C21—H21	0.9500
C1—C2	1.388 (2)	C24—C25	1.512 (2)
C1—C6	1.404 (2)	C24—H24A	0.9900
C2—C3	1.381 (2)	C24—H24B	0.9900
C2—H2	0.9500	C26—H26A	0.9800
C3—C4	1.389 (2)	C26—H26B	0.9800
C3—H3	0.9500	C26—H26C	0.9800
C4—C5	1.380 (3)	C27—C32	1.378 (3)
C4—H4	0.9500	C27—C28	1.383 (2)
C5—C6	1.392 (2)	C28—C29	1.383 (3)
C5—H5	0.9500	C28—H28	0.9500
C8—C9	1.514 (2)	C29—C30	1.372 (3)
C8—H8A	0.9900	C29—H29	0.9500
C8—H8B	0.9900	C30—C31	1.373 (3)
C10—H10A	0.9800	C30—H30	0.9500
C10—H10B	0.9800	C31—C32	1.383 (3)
C10—H10C	0.9800	C31—H31	0.9500
C11—C16	1.381 (3)	C32—H32	0.9500

C1—S1—C7	87.44 (8)	C14—C15—C16	119.9 (2)
C17—S2—C23	87.60 (9)	C14—C15—H15	120.0
C7—O1—C8	114.32 (13)	C16—C15—H15	120.0
C23—O3—C24	115.36 (13)	C15—C16—C11	119.62 (19)
C7—N1—C6	108.91 (14)	C15—C16—H16	120.2
C9—N2—C11	122.22 (14)	C11—C16—H16	120.2
C9—N2—C10	119.78 (15)	C18—C17—C22	121.31 (19)
C11—N2—C10	116.67 (14)	C18—C17—S2	128.87 (16)
C23—N3—C22	108.79 (14)	C22—C17—S2	109.82 (13)
C25—N4—C27	122.21 (15)	C19—C18—C17	117.9 (2)
C25—N4—C26	119.92 (16)	C19—C18—H18	121.1
C27—N4—C26	117.75 (15)	C17—C18—H18	121.1
C2—C1—C6	121.92 (16)	C18—C19—C20	121.3 (2)
C2—C1—S1	128.66 (13)	C18—C19—H19	119.4
C6—C1—S1	109.41 (12)	C20—C19—H19	119.4
C3—C2—C1	117.71 (15)	C21—C20—C19	121.3 (2)
C3—C2—H2	121.1	C21—C20—H20	119.3
C1—C2—H2	121.1	C19—C20—H20	119.3
C2—C3—C4	121.00 (17)	C20—C21—C22	118.0 (2)
C2—C3—H3	119.5	C20—C21—H21	121.0
C4—C3—H3	119.5	C22—C21—H21	121.0
C5—C4—C3	121.36 (17)	C21—C22—C17	120.17 (17)
C5—C4—H4	119.3	C21—C22—N3	124.66 (17)
C3—C4—H4	119.3	C17—C22—N3	115.17 (16)
C4—C5—C6	118.74 (16)	N3—C23—O3	126.29 (15)
C4—C5—H5	120.6	N3—C23—S2	118.62 (14)
C6—C5—H5	120.6	O3—C23—S2	115.07 (12)
C5—C6—N1	125.27 (15)	O3—C24—C25	110.61 (14)
C5—C6—C1	119.25 (15)	O3—C24—H24A	109.5
N1—C6—C1	115.47 (14)	C25—C24—H24A	109.5
N1—C7—O1	125.72 (15)	O3—C24—H24B	109.5
N1—C7—S1	118.76 (13)	C25—C24—H24B	109.5
O1—C7—S1	115.52 (12)	H24A—C24—H24B	108.1
O1—C8—C9	110.98 (14)	O4—C25—N4	123.28 (17)
O1—C8—H8A	109.4	O4—C25—C24	121.98 (15)
C9—C8—H8A	109.4	N4—C25—C24	114.64 (15)
O1—C8—H8B	109.4	N4—C26—H26A	109.5
C9—C8—H8B	109.4	N4—C26—H26B	109.5
H8A—C8—H8B	108.0	H26A—C26—H26B	109.5
O2—C9—N2	123.28 (16)	N4—C26—H26C	109.5
O2—C9—C8	121.62 (16)	H26A—C26—H26C	109.5
N2—C9—C8	115.11 (14)	H26B—C26—H26C	109.5
N2—C10—H10A	109.5	C32—C27—C28	120.39 (17)
N2—C10—H10B	109.5	C32—C27—N4	120.35 (16)
H10A—C10—H10B	109.5	C28—C27—N4	119.26 (17)
N2—C10—H10C	109.5	C27—C28—C29	119.74 (18)
H10A—C10—H10C	109.5	C27—C28—H28	120.1
H10B—C10—H10C	109.5	C29—C28—H28	120.1
C16—C11—C12	120.63 (17)	C30—C29—C28	120.13 (18)
C16—C11—N2	119.09 (16)	C30—C29—H29	119.9
C12—C11—N2	120.25 (16)	C28—C29—H29	119.9
C11—C12—C13	119.13 (19)	C29—C30—C31	119.76 (18)
C11—C12—H12	120.4	C29—C30—H30	120.1
C13—C12—H12	120.4	C31—C30—H30	120.1
C14—C13—C12	120.3 (2)	C30—C31—C32	120.97 (19)
C14—C13—H13	119.8	C30—C31—H31	119.5
C12—C13—H13	119.8	C32—C31—H31	119.5
C15—C14—C13	120.40 (19)	C27—C32—C31	119.01 (18)
C15—C14—H14	119.8	C27—C32—H32	120.5
C13—C14—H14	119.8	C31—C32—H32	120.5

C7—S1—C1—C2	−178.11 (17)	C23—S2—C17—C18	179.84 (17)
C7—S1—C1—C6	0.69 (13)	C23—S2—C17—C22	0.07 (13)
C6—C1—C2—C3	−0.5 (3)	C22—C17—C18—C19	−1.3 (3)
S1—C1—C2—C3	178.19 (14)	S2—C17—C18—C19	178.94 (15)
C1—C2—C3—C4	0.9 (3)	C17—C18—C19—C20	1.2 (3)
C2—C3—C4—C5	−0.5 (3)	C18—C19—C20—C21	−0.2 (3)
C3—C4—C5—C6	−0.4 (3)	C19—C20—C21—C22	−0.7 (3)
C4—C5—C6—N1	−178.22 (16)	C20—C21—C22—C17	0.6 (3)
C4—C5—C6—C1	0.8 (3)	C20—C21—C22—N3	−179.19 (17)
C7—N1—C6—C5	178.35 (17)	C18—C17—C22—C21	0.4 (3)
C7—N1—C6—C1	−0.7 (2)	S2—C17—C22—C21	−179.77 (13)
C2—C1—C6—C5	−0.4 (3)	C18—C17—C22—N3	−179.76 (15)
S1—C1—C6—C5	−179.29 (13)	S2—C17—C22—N3	0.03 (18)
C2—C1—C6—N1	178.75 (15)	C23—N3—C22—C21	179.63 (16)
S1—C1—C6—N1	−0.15 (19)	C23—N3—C22—C17	−0.2 (2)
C6—N1—C7—O1	−179.10 (16)	C22—N3—C23—O3	178.61 (15)
C6—N1—C7—S1	1.35 (19)	C22—N3—C23—S2	0.22 (18)
C8—O1—C7—N1	5.5 (2)	C24—O3—C23—N3	−6.3 (2)
C8—O1—C7—S1	−174.96 (12)	C24—O3—C23—S2	172.16 (11)
C1—S1—C7—N1	−1.25 (15)	C17—S2—C23—N3	−0.18 (14)
C1—S1—C7—O1	179.15 (14)	C17—S2—C23—O3	−178.75 (13)
C7—O1—C8—C9	69.22 (18)	C23—O3—C24—C25	86.56 (17)
C11—N2—C9—O2	170.94 (16)	C27—N4—C25—O4	−176.47 (17)
C10—N2—C9—O2	4.6 (3)	C26—N4—C25—O4	−0.5 (3)
C11—N2—C9—C8	−8.7 (2)	C27—N4—C25—C24	7.3 (2)
C10—N2—C9—C8	−175.05 (16)	C26—N4—C25—C24	−176.75 (18)
O1—C8—C9—O2	8.8 (2)	O3—C24—C25—O4	10.1 (2)
O1—C8—C9—N2	−171.57 (14)	O3—C24—C25—N4	−173.56 (15)
C9—N2—C11—C16	−87.7 (2)	C25—N4—C27—C32	−98.8 (2)
C10—N2—C11—C16	79.1 (2)	C26—N4—C27—C32	85.1 (2)
C9—N2—C11—C12	94.2 (2)	C25—N4—C27—C28	81.6 (2)
C10—N2—C11—C12	−99.0 (2)	C26—N4—C27—C28	−94.4 (2)
C16—C11—C12—C13	0.0 (3)	C32—C27—C28—C29	0.1 (3)
N2—C11—C12—C13	178.08 (17)	N4—C27—C28—C29	179.57 (16)
C11—C12—C13—C14	−0.6 (3)	C27—C28—C29—C30	−0.3 (3)
C12—C13—C14—C15	0.9 (4)	C28—C29—C30—C31	0.4 (3)
C13—C14—C15—C16	−0.6 (3)	C29—C30—C31—C32	−0.2 (3)
C14—C15—C16—C11	0.1 (3)	C28—C27—C32—C31	0.1 (3)
C12—C11—C16—C15	0.2 (3)	N4—C27—C32—C31	−179.41 (17)
N2—C11—C16—C15	−177.86 (18)	C30—C31—C32—C27	0.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg,1 Cg2 and Cg3 are the centroids of the C27–C32, C17–C22 and S1/C1/C6/N1/C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4ⁱ	0.95	2.44	3.273 (2)	147
C8—H8B···O3ⁱⁱ	0.99	2.43	3.235 (2)	138
C24—H24B···O2	0.99	2.35	3.256 (2)	153
C15—H15···Cg1ⁱⁱ	0.95	2.97	3.84	154
C26—H26B···Cg2ⁱⁱⁱ	0.98	3.00	3.74	134
C29—H29···Cg3^iv	0.95	2.95	3.74	141
C30—H30···Cg2ⁱ	0.95	2.80	3.42	124

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+1/2; (iv) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₂S
M_r	298.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	11.2708 (6), 15.7112 (9), 19.9579 (8)
β (°)	122.997 (2)
V (Å³)	2964.0 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.19 × 0.17 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.959, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	30345, 7338, 5174
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.107, 1.02
No. of reflections	7338
No. of parameters	381
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.28

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

Cg,1 Cg2 and Cg3 are the centroids of the C27–C32, C17–C22 and S1/C1/C6/N1/C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4ⁱ	0.95	2.44	3.273 (2)	146.6
C8—H8B···O3ⁱⁱ	0.99	2.43	3.235 (2)	138.2
C24—H24B···O2	0.99	2.35	3.256 (2)	152.5
C15—H15···Cg1ⁱⁱ	0.95	2.97	3.84	153.5
C26—H26B···Cg2ⁱⁱⁱ	0.98	3.00	3.74	134.1
C29—H29···Cg3^iv	0.95	2.95	3.74	140.7
C30—H30···Cg2ⁱ	0.95	2.80	3.42	124.0

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+1/2; (iv) x, −y+3/2, z−1/2.

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (grant No. 2010-0016386).

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lu, Y., Han, S. & Zhang, C. (2001). Bull. Environ. Contam. Toxicol. 66, 17–23. PubMed Google Scholar
Murru, S., Mondal, P., Yella, R. & Patel, B. K. (2009). Eur. J. Org. Chem. 31, 5406–5413. Web of Science CSD CrossRef 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

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