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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Lu, Y., Han, S. & Zhang, C. (2001). Bull. Environ. Contam. Toxicol. 66, 17-23.]). For related structures, see: Murru et al. (2009[Murru, S., Mondal, P., Yella, R. & Patel, B. K. (2009). Eur. J. Org. Chem. 31, 5406-5413.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14N2O2S

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.959, Tmax = 0.980

  • 30345 measured reflections

  • 7338 independent reflections

  • 5174 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.107

  • S = 1.02

  • 7338 reflections

  • 381 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −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 DA 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—H26BCg2iii 0.98 3.00 3.74 134
C29—H29⋯Cg3iv 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[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.95 Å, Uiso(H) = 1.2Ueq(C) for aromatic C, d(C—H) = 0.99 Å, Uiso(H) = 1.2Ueq(C) for CH2 and d(C—H) = 0.98 Å, Uiso(H) = 1.5Ueq(C) for CH3 groups.

Structure description 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.

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
[Figure 1] 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.
[Figure 2] 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
C16H14N2O2SF(000) = 1248
Mr = 298.35Dx = 1.337 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5175 reflections
a = 11.2708 (6) Åθ = 2.2–25.3°
b = 15.7112 (9) ŵ = 0.22 mm1
c = 19.9579 (8) ÅT = 173 K
β = 122.997 (2)°Block, colourless
V = 2964.0 (3) Å30.19 × 0.17 × 0.09 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer
7338 independent reflections
Radiation source: fine-focus sealed tube5174 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
φ and ω scansθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.959, Tmax = 0.980k = 1820
30345 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0435P)2 + 0.7531P]
where P = (Fo2 + 2Fc2)/3
7338 reflections(Δ/σ)max = 0.001
381 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C16H14N2O2SV = 2964.0 (3) Å3
Mr = 298.35Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.2708 (6) ŵ = 0.22 mm1
b = 15.7112 (9) ÅT = 173 K
c = 19.9579 (8) Å0.19 × 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)
Tmin = 0.959, Tmax = 0.980Rint = 0.045
30345 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.02Δρmax = 0.27 e Å3
7338 reflectionsΔρmin = 0.28 e Å3
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
xyzUiso*/Ueq
S10.94569 (4)0.65520 (3)0.70419 (3)0.03607 (12)
S20.21697 (5)0.53839 (3)0.15747 (3)0.03835 (13)
O10.71887 (12)0.56299 (8)0.65599 (8)0.0371 (3)
O20.53812 (13)0.61502 (8)0.50454 (8)0.0407 (3)
O30.37291 (13)0.62655 (7)0.28811 (7)0.0358 (3)
O40.30217 (13)0.78901 (8)0.29306 (9)0.0462 (3)
N10.69842 (14)0.70886 (9)0.66837 (9)0.0310 (3)
N20.34408 (15)0.59934 (9)0.51009 (9)0.0344 (3)
N30.38648 (14)0.66403 (9)0.17928 (8)0.0310 (3)
N40.52868 (15)0.83502 (9)0.36531 (10)0.0402 (4)
C10.92417 (17)0.76410 (11)0.71071 (10)0.0289 (4)
C21.02172 (17)0.82906 (12)0.73152 (10)0.0338 (4)
H21.11560.81730.74620.041*
C30.97758 (19)0.91139 (12)0.73012 (11)0.0366 (4)
H31.04180.95720.74340.044*
C40.84079 (19)0.92827 (12)0.70967 (11)0.0376 (4)
H40.81330.98550.70960.045*
C50.74394 (18)0.86369 (11)0.68950 (11)0.0356 (4)
H50.65080.87600.67590.043*
C60.78526 (17)0.78025 (11)0.68938 (10)0.0285 (4)
C70.76859 (17)0.64308 (11)0.67289 (10)0.0304 (4)
C80.57044 (18)0.55577 (11)0.62402 (11)0.0349 (4)
H8A0.54810.58610.65930.042*
H8B0.54540.49500.62230.042*
C90.48359 (18)0.59301 (10)0.54072 (10)0.0311 (4)
C100.2484 (2)0.62796 (14)0.42757 (11)0.0465 (5)
H10A0.30060.66360.41180.070*
H10B0.17100.66100.42350.070*
H10C0.20950.57840.39220.070*
C110.27959 (17)0.56221 (11)0.54862 (10)0.0324 (4)
C120.2600 (2)0.61034 (13)0.59977 (12)0.0417 (4)
H120.29150.66770.61110.050*
C130.1940 (2)0.57392 (16)0.63416 (13)0.0555 (6)
H130.18070.60630.66980.067*
C140.1474 (2)0.49112 (16)0.61706 (14)0.0575 (6)
H140.10090.46680.64040.069*
C150.1676 (2)0.44331 (14)0.56647 (14)0.0540 (6)
H150.13610.38590.55530.065*
C160.2339 (2)0.47876 (12)0.53191 (12)0.0423 (5)
H160.24810.44600.49680.051*
C170.23107 (18)0.56733 (11)0.07802 (11)0.0351 (4)
C180.1640 (2)0.53245 (13)0.00209 (13)0.0489 (5)
H180.10120.48560.01260.059*
C190.1912 (2)0.56794 (16)0.05143 (14)0.0589 (6)
H190.14500.54580.10410.071*
C200.2847 (3)0.63537 (15)0.02975 (13)0.0555 (6)
H200.30150.65840.06790.067*
C210.3540 (2)0.66979 (13)0.04629 (12)0.0431 (5)
H210.41880.71550.06100.052*
C220.32599 (18)0.63536 (11)0.10061 (11)0.0323 (4)
C230.33790 (17)0.61924 (10)0.21272 (10)0.0300 (4)
C240.48587 (18)0.68520 (11)0.33700 (11)0.0337 (4)
H24A0.55520.68420.32110.040*
H24B0.53520.66750.39370.040*
C250.42889 (18)0.77450 (11)0.32799 (11)0.0335 (4)
C260.4871 (2)0.92358 (13)0.36470 (17)0.0638 (7)
H26A0.49250.95570.32440.096*
H26B0.55100.94900.41740.096*
H26C0.38990.92520.35190.096*
C270.67722 (18)0.81716 (11)0.40232 (11)0.0333 (4)
C280.73303 (19)0.81424 (12)0.35549 (12)0.0387 (4)
H280.67370.82350.29950.046*
C290.87550 (19)0.79774 (12)0.39043 (12)0.0416 (5)
H290.91410.79540.35840.050*
C300.9613 (2)0.78468 (12)0.47130 (13)0.0432 (5)
H301.05920.77370.49530.052*
C310.9050 (2)0.78758 (14)0.51738 (13)0.0495 (5)
H310.96460.77830.57330.059*
C320.7627 (2)0.80379 (13)0.48354 (12)0.0455 (5)
H320.72450.80570.51580.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0286 (2)0.0329 (2)0.0472 (3)0.00576 (18)0.0210 (2)0.0021 (2)
S20.0339 (2)0.0301 (2)0.0484 (3)0.00813 (18)0.0207 (2)0.0074 (2)
O10.0329 (6)0.0308 (6)0.0433 (8)0.0001 (5)0.0178 (6)0.0011 (6)
O20.0446 (7)0.0475 (8)0.0369 (7)0.0051 (6)0.0266 (6)0.0006 (6)
O30.0383 (7)0.0326 (7)0.0316 (7)0.0099 (5)0.0158 (6)0.0015 (5)
O40.0305 (7)0.0413 (8)0.0622 (9)0.0038 (6)0.0224 (7)0.0042 (7)
N10.0274 (7)0.0329 (8)0.0328 (8)0.0009 (6)0.0166 (6)0.0005 (6)
N20.0366 (8)0.0372 (8)0.0296 (8)0.0020 (6)0.0182 (7)0.0050 (6)
N30.0318 (7)0.0276 (7)0.0305 (8)0.0017 (6)0.0150 (7)0.0006 (6)
N40.0319 (8)0.0315 (8)0.0582 (11)0.0043 (6)0.0251 (8)0.0048 (7)
C10.0275 (8)0.0324 (9)0.0260 (9)0.0048 (7)0.0141 (7)0.0031 (7)
C20.0241 (8)0.0420 (10)0.0323 (10)0.0011 (7)0.0134 (7)0.0003 (8)
C30.0364 (9)0.0349 (10)0.0366 (10)0.0042 (8)0.0187 (8)0.0015 (8)
C40.0411 (10)0.0322 (9)0.0399 (11)0.0034 (8)0.0223 (9)0.0004 (8)
C50.0293 (9)0.0365 (10)0.0417 (11)0.0053 (7)0.0199 (8)0.0004 (8)
C60.0265 (8)0.0328 (9)0.0258 (9)0.0027 (7)0.0140 (7)0.0006 (7)
C70.0278 (8)0.0330 (9)0.0295 (9)0.0002 (7)0.0150 (7)0.0007 (7)
C80.0327 (9)0.0339 (10)0.0350 (10)0.0049 (7)0.0165 (8)0.0027 (8)
C90.0384 (9)0.0250 (8)0.0311 (9)0.0031 (7)0.0196 (8)0.0038 (7)
C100.0461 (11)0.0539 (13)0.0334 (11)0.0082 (9)0.0177 (9)0.0084 (9)
C110.0283 (8)0.0356 (9)0.0315 (10)0.0035 (7)0.0151 (8)0.0042 (7)
C120.0452 (11)0.0407 (11)0.0429 (11)0.0015 (9)0.0264 (10)0.0051 (9)
C130.0553 (13)0.0748 (16)0.0501 (14)0.0038 (12)0.0376 (12)0.0081 (12)
C140.0472 (12)0.0788 (17)0.0521 (14)0.0115 (12)0.0306 (11)0.0092 (12)
C150.0529 (13)0.0469 (12)0.0608 (15)0.0128 (10)0.0300 (12)0.0017 (11)
C160.0423 (11)0.0399 (11)0.0453 (12)0.0020 (8)0.0241 (10)0.0051 (9)
C170.0275 (8)0.0321 (9)0.0388 (11)0.0062 (7)0.0135 (8)0.0040 (8)
C180.0395 (11)0.0462 (12)0.0494 (13)0.0059 (9)0.0168 (10)0.0157 (10)
C190.0596 (14)0.0667 (15)0.0420 (13)0.0114 (12)0.0223 (11)0.0172 (11)
C200.0678 (15)0.0621 (15)0.0446 (13)0.0160 (12)0.0358 (12)0.0015 (11)
C210.0487 (11)0.0435 (11)0.0429 (12)0.0087 (9)0.0287 (10)0.0040 (9)
C220.0307 (8)0.0294 (9)0.0328 (10)0.0071 (7)0.0147 (8)0.0001 (7)
C230.0269 (8)0.0242 (8)0.0331 (10)0.0015 (6)0.0125 (7)0.0006 (7)
C240.0317 (9)0.0327 (9)0.0280 (9)0.0070 (7)0.0107 (8)0.0016 (7)
C250.0325 (9)0.0352 (10)0.0351 (10)0.0056 (7)0.0199 (8)0.0019 (8)
C260.0457 (12)0.0342 (11)0.114 (2)0.0049 (9)0.0448 (14)0.0109 (12)
C270.0303 (9)0.0295 (9)0.0397 (11)0.0070 (7)0.0187 (8)0.0045 (8)
C280.0376 (10)0.0405 (10)0.0360 (11)0.0051 (8)0.0187 (9)0.0042 (8)
C290.0371 (10)0.0460 (11)0.0475 (12)0.0053 (8)0.0268 (10)0.0003 (9)
C300.0320 (10)0.0363 (10)0.0516 (13)0.0067 (8)0.0165 (9)0.0053 (9)
C310.0445 (11)0.0561 (13)0.0308 (11)0.0048 (10)0.0095 (9)0.0039 (9)
C320.0510 (12)0.0508 (12)0.0408 (12)0.0065 (10)0.0289 (10)0.0090 (9)
Geometric parameters (Å, º) top
S1—C11.7428 (17)C11—C121.381 (3)
S1—C71.7472 (17)C12—C131.382 (3)
S2—C171.738 (2)C12—H120.9500
S2—C231.7465 (17)C13—C141.375 (3)
O1—C71.344 (2)C13—H130.9500
O1—C81.434 (2)C14—C151.374 (3)
O2—C91.226 (2)C14—H140.9500
O3—C231.336 (2)C15—C161.380 (3)
O3—C241.438 (2)C15—H150.9500
O4—C251.222 (2)C16—H160.9500
N1—C71.274 (2)C17—C181.386 (3)
N1—C61.395 (2)C17—C221.402 (2)
N2—C91.345 (2)C18—C191.380 (3)
N2—C111.438 (2)C18—H180.9500
N2—C101.464 (2)C19—C201.387 (3)
N3—C231.280 (2)C19—H190.9500
N3—C221.403 (2)C20—C211.384 (3)
N4—C251.346 (2)C20—H200.9500
N4—C271.442 (2)C21—C221.393 (3)
N4—C261.466 (2)C21—H210.9500
C1—C21.388 (2)C24—C251.512 (2)
C1—C61.404 (2)C24—H24A0.9900
C2—C31.381 (2)C24—H24B0.9900
C2—H20.9500C26—H26A0.9800
C3—C41.389 (2)C26—H26B0.9800
C3—H30.9500C26—H26C0.9800
C4—C51.380 (3)C27—C321.378 (3)
C4—H40.9500C27—C281.383 (2)
C5—C61.392 (2)C28—C291.383 (3)
C5—H50.9500C28—H280.9500
C8—C91.514 (2)C29—C301.372 (3)
C8—H8A0.9900C29—H290.9500
C8—H8B0.9900C30—C311.373 (3)
C10—H10A0.9800C30—H300.9500
C10—H10B0.9800C31—C321.383 (3)
C10—H10C0.9800C31—H310.9500
C11—C161.381 (3)C32—H320.9500
C1—S1—C787.44 (8)C14—C15—C16119.9 (2)
C17—S2—C2387.60 (9)C14—C15—H15120.0
C7—O1—C8114.32 (13)C16—C15—H15120.0
C23—O3—C24115.36 (13)C15—C16—C11119.62 (19)
C7—N1—C6108.91 (14)C15—C16—H16120.2
C9—N2—C11122.22 (14)C11—C16—H16120.2
C9—N2—C10119.78 (15)C18—C17—C22121.31 (19)
C11—N2—C10116.67 (14)C18—C17—S2128.87 (16)
C23—N3—C22108.79 (14)C22—C17—S2109.82 (13)
C25—N4—C27122.21 (15)C19—C18—C17117.9 (2)
C25—N4—C26119.92 (16)C19—C18—H18121.1
C27—N4—C26117.75 (15)C17—C18—H18121.1
C2—C1—C6121.92 (16)C18—C19—C20121.3 (2)
C2—C1—S1128.66 (13)C18—C19—H19119.4
C6—C1—S1109.41 (12)C20—C19—H19119.4
C3—C2—C1117.71 (15)C21—C20—C19121.3 (2)
C3—C2—H2121.1C21—C20—H20119.3
C1—C2—H2121.1C19—C20—H20119.3
C2—C3—C4121.00 (17)C20—C21—C22118.0 (2)
C2—C3—H3119.5C20—C21—H21121.0
C4—C3—H3119.5C22—C21—H21121.0
C5—C4—C3121.36 (17)C21—C22—C17120.17 (17)
C5—C4—H4119.3C21—C22—N3124.66 (17)
C3—C4—H4119.3C17—C22—N3115.17 (16)
C4—C5—C6118.74 (16)N3—C23—O3126.29 (15)
C4—C5—H5120.6N3—C23—S2118.62 (14)
C6—C5—H5120.6O3—C23—S2115.07 (12)
C5—C6—N1125.27 (15)O3—C24—C25110.61 (14)
C5—C6—C1119.25 (15)O3—C24—H24A109.5
N1—C6—C1115.47 (14)C25—C24—H24A109.5
N1—C7—O1125.72 (15)O3—C24—H24B109.5
N1—C7—S1118.76 (13)C25—C24—H24B109.5
O1—C7—S1115.52 (12)H24A—C24—H24B108.1
O1—C8—C9110.98 (14)O4—C25—N4123.28 (17)
O1—C8—H8A109.4O4—C25—C24121.98 (15)
C9—C8—H8A109.4N4—C25—C24114.64 (15)
O1—C8—H8B109.4N4—C26—H26A109.5
C9—C8—H8B109.4N4—C26—H26B109.5
H8A—C8—H8B108.0H26A—C26—H26B109.5
O2—C9—N2123.28 (16)N4—C26—H26C109.5
O2—C9—C8121.62 (16)H26A—C26—H26C109.5
N2—C9—C8115.11 (14)H26B—C26—H26C109.5
N2—C10—H10A109.5C32—C27—C28120.39 (17)
N2—C10—H10B109.5C32—C27—N4120.35 (16)
H10A—C10—H10B109.5C28—C27—N4119.26 (17)
N2—C10—H10C109.5C27—C28—C29119.74 (18)
H10A—C10—H10C109.5C27—C28—H28120.1
H10B—C10—H10C109.5C29—C28—H28120.1
C16—C11—C12120.63 (17)C30—C29—C28120.13 (18)
C16—C11—N2119.09 (16)C30—C29—H29119.9
C12—C11—N2120.25 (16)C28—C29—H29119.9
C11—C12—C13119.13 (19)C29—C30—C31119.76 (18)
C11—C12—H12120.4C29—C30—H30120.1
C13—C12—H12120.4C31—C30—H30120.1
C14—C13—C12120.3 (2)C30—C31—C32120.97 (19)
C14—C13—H13119.8C30—C31—H31119.5
C12—C13—H13119.8C32—C31—H31119.5
C15—C14—C13120.40 (19)C27—C32—C31119.01 (18)
C15—C14—H14119.8C27—C32—H32120.5
C13—C14—H14119.8C31—C32—H32120.5
C7—S1—C1—C2178.11 (17)C23—S2—C17—C18179.84 (17)
C7—S1—C1—C60.69 (13)C23—S2—C17—C220.07 (13)
C6—C1—C2—C30.5 (3)C22—C17—C18—C191.3 (3)
S1—C1—C2—C3178.19 (14)S2—C17—C18—C19178.94 (15)
C1—C2—C3—C40.9 (3)C17—C18—C19—C201.2 (3)
C2—C3—C4—C50.5 (3)C18—C19—C20—C210.2 (3)
C3—C4—C5—C60.4 (3)C19—C20—C21—C220.7 (3)
C4—C5—C6—N1178.22 (16)C20—C21—C22—C170.6 (3)
C4—C5—C6—C10.8 (3)C20—C21—C22—N3179.19 (17)
C7—N1—C6—C5178.35 (17)C18—C17—C22—C210.4 (3)
C7—N1—C6—C10.7 (2)S2—C17—C22—C21179.77 (13)
C2—C1—C6—C50.4 (3)C18—C17—C22—N3179.76 (15)
S1—C1—C6—C5179.29 (13)S2—C17—C22—N30.03 (18)
C2—C1—C6—N1178.75 (15)C23—N3—C22—C21179.63 (16)
S1—C1—C6—N10.15 (19)C23—N3—C22—C170.2 (2)
C6—N1—C7—O1179.10 (16)C22—N3—C23—O3178.61 (15)
C6—N1—C7—S11.35 (19)C22—N3—C23—S20.22 (18)
C8—O1—C7—N15.5 (2)C24—O3—C23—N36.3 (2)
C8—O1—C7—S1174.96 (12)C24—O3—C23—S2172.16 (11)
C1—S1—C7—N11.25 (15)C17—S2—C23—N30.18 (14)
C1—S1—C7—O1179.15 (14)C17—S2—C23—O3178.75 (13)
C7—O1—C8—C969.22 (18)C23—O3—C24—C2586.56 (17)
C11—N2—C9—O2170.94 (16)C27—N4—C25—O4176.47 (17)
C10—N2—C9—O24.6 (3)C26—N4—C25—O40.5 (3)
C11—N2—C9—C88.7 (2)C27—N4—C25—C247.3 (2)
C10—N2—C9—C8175.05 (16)C26—N4—C25—C24176.75 (18)
O1—C8—C9—O28.8 (2)O3—C24—C25—O410.1 (2)
O1—C8—C9—N2171.57 (14)O3—C24—C25—N4173.56 (15)
C9—N2—C11—C1687.7 (2)C25—N4—C27—C3298.8 (2)
C10—N2—C11—C1679.1 (2)C26—N4—C27—C3285.1 (2)
C9—N2—C11—C1294.2 (2)C25—N4—C27—C2881.6 (2)
C10—N2—C11—C1299.0 (2)C26—N4—C27—C2894.4 (2)
C16—C11—C12—C130.0 (3)C32—C27—C28—C290.1 (3)
N2—C11—C12—C13178.08 (17)N4—C27—C28—C29179.57 (16)
C11—C12—C13—C140.6 (3)C27—C28—C29—C300.3 (3)
C12—C13—C14—C150.9 (4)C28—C29—C30—C310.4 (3)
C13—C14—C15—C160.6 (3)C29—C30—C31—C320.2 (3)
C14—C15—C16—C110.1 (3)C28—C27—C32—C310.1 (3)
C12—C11—C16—C150.2 (3)N4—C27—C32—C31179.41 (17)
N2—C11—C16—C15177.86 (18)C30—C31—C32—C270.0 (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···AD—HH···AD···AD—H···A
C2—H2···O4i0.952.443.273 (2)147
C8—H8B···O3ii0.992.433.235 (2)138
C24—H24B···O20.992.353.256 (2)153
C15—H15···Cg1ii0.952.973.84154
C26—H26B···Cg2iii0.983.003.74134
C29—H29···Cg3iv0.952.953.74141
C30—H30···Cg2i0.952.803.42124
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, z1/2.

Experimental details

Crystal data
Chemical formulaC16H14N2O2S
Mr298.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)11.2708 (6), 15.7112 (9), 19.9579 (8)
β (°) 122.997 (2)
V3)2964.0 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.19 × 0.17 × 0.09
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.959, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
30345, 7338, 5174
Rint0.045
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.107, 1.02
No. of reflections7338
No. of parameters381
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C2—H2···O4i0.952.443.273 (2)146.6
C8—H8B···O3ii0.992.433.235 (2)138.2
C24—H24B···O20.992.353.256 (2)152.5
C15—H15···Cg1ii0.952.973.84153.5
C26—H26B···Cg2iii0.983.003.74134.1
C29—H29···Cg3iv0.952.953.74140.7
C30—H30···Cg2i0.952.803.42124.0
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, z1/2.
 

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

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLu, Y., Han, S. & Zhang, C. (2001). Bull. Environ. Contam. Toxicol. 66, 17–23.  PubMed Google Scholar
First citationMurru, S., Mondal, P., Yella, R. & Patel, B. K. (2009). Eur. J. Org. Chem. 31, 5406–5413.  Web of Science CSD CrossRef Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds