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ISSN: 2056-9890

(Z)-3-(3,4-Di­meth­­oxy­benz­yl)-1,5-benzo­thia­zepin-4(5H)-one

aDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India, bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India, cDepartment of Physics, Sri Balaji Chokkalingam Engineering College, Arni, Thiruvannamalai 632 317, India, and dDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
*Correspondence e-mail: smurugavel27@gmail.com

(Received 1 April 2013; accepted 8 April 2013; online 13 April 2013)

In the title compound, C18H17NO3S, the thia­zepine ring adopts a slightly distorted twist-boat conformation. The dihedral angle between the mean plane of the benzo­thia­zepin ring system and the benzene ring is 60.3 (1)°. In the crystal, mol­ecules are linked by two pairs of inversion-related N—H⋯O and C—H⋯O hydrogen bonds, generating alternating R22(8) and R22(6) ring motifs, respectively, in a zigzag supra­molecular chain that runs along the c axis. These chains stack along the a axis via S⋯C [3.424 (2) Å] contacts. A three-dimensional supra­molecular network is consolidated by C—H⋯π and ππ inter­actions [inter-centroid distance between di­meth­oxy­benzene rings = 3.815 (1) Å]. The crystal studied was a non-merohedral twin, with a refined value of the minor twin fraction of 0.2477 (6) .

Related literature

For background to the biology of thia­zepine derivatives and for a related structure, see: Bakthadoss et al. (2013[Bakthadoss, M., Selvakumar, R., Manikandan, N. & Murugavel, S. (2013). Acta Cryst. E69, o562-o563.]). For ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C18H17NO3S

  • Mr = 327.39

  • Orthorhombic, P b c n

  • a = 19.966 (4) Å

  • b = 10.355 (2) Å

  • c = 15.536 (3) Å

  • V = 3212.0 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 293 K

  • 0.35 × 0.20 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (TWINABS; Sheldrick, 1997[Sheldrick, G. M. (1997). TWINABS. University of Göttingen, Germany.]) Tmin = 0.927, Tmax = 0.968

  • 13227 measured reflections

  • 13227 independent reflections

  • 8413 reflections with I > 2σ(I)

  • Rint = 0.066

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.175

  • S = 1.02

  • 13227 reflections

  • 211 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C11–C16 and C2–C7 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O1i 0.86 2.02 2.863 (2) 167
C18—H18B⋯O3ii 0.96 2.53 3.445 (3) 159
C4—H4⋯Cg1iii 0.93 2.57 3.450 (2) 158
C10—H10BCg2iv 0.97 2.82 3.725 (2) 155
Symmetry codes: (i) -x, -y, -z+2; (ii) -x, -y+1, -z+1; (iii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [x, -y, z-{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The background to the biology and related structure of thiazepin derivatives, has been described recently (Bakthadoss et al., 2013). In view of this biological importance, the crystal structure of the title compound has been carried out and the results are presented here.

Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The seven membered thiazepine ring (N1/S1/C1/C2/C7/C8/C9) adopts slightly distorted twist-boat conformation as indicated by puckering parameters (Cremer & Pople, 1975): QT = 0.9884 (11) Å, φ2 = 359.3 (1)° and φ3 = 356.5 (4)°. The dihedral angle between the benzothiazepin ring system and the benzene ring is 60.3 (1)°. The atom O1 deviates by -0.895 (1) Å from the least-squares plane of the thiazepin ring. The sum of angles at N1 atom of the thiazepin ring (359.9°) is in accordance with sp2 hybridization. The geometric parameters of the title molecule agree well with those reported for a similar structure (Bakthadoss et al., 2013).

In the crystal, molecules are linked by two pairs of inversion-related N1—H1A···O1 and C18—H18B···O3 hydrogen bonds, generating alternate R22(8) and R22(6) ring motifs, respectively, resulting in a zigzag supramolecular chain running along the c axis. These chains stack along the a axis by S1···C4v = 3.424 (2) Å (Symmetry code:(v) = 1/2 - x, -1/2 + y, z) short contacts (Fig. 2 and Table 1). A three-dimensional supramolecular network is consolidated by C4—H4···Cg1iii (symmetry code: (iii) = 1/2 - x, 1/2 - y, 1/2 + z) and C10—H10B···Cg2iv (symmetry code: (iv) = x, -y, -1/2 + z) hydrogen bonds and Cg1—Cg1vi = 3.815 (1) Å (symmetry code: (vi) = -x, y, 3/2 - z) interactions (Fig. 3 and Table 1; Cg1 and Cg2 are the centroids of the C11–C16 and C2–C7 benzene rings, respectively).

Related literature top

For background to the biology of thiazepin derivatives and for a related structure, see: Bakthadoss et al. (2013). For ring-puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of (Z)-methyl 2-(bromomethyl)-3-(3,4-dimethoxyphenyl)acrylate 2 mmol) and o-aminothiophenol (2 mmol) in the presence of potassium tert-butoxide (4.8 mmol) in dry THF (10 ml) was stirred at room temperature for 1 h. After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (20 ml) and extracted with ethyl acetate (3 x 20 ml). The organic layer was washed with brine (2 x 20 ml) and dried over anhydrous sodium sulfate. The organic layer was concentrated, which successfully provide the crude final product ((Z)-3-(3,4-dimethoxybenzyl)benzo[b][1,4]thiazepin-4(5H)-one). This product was purified by column chromatography on silica gel to afford the title compound in good yield (44%). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of its ethylacetate solution at room temperature.

Refinement top

The investigated crystal was found to be a two-component rotational twin. The data for both components were integrated using SAINT and scaled with TWINABS. Final refinement was perfomed using a HKLF5 file generated by TWINABS with a BASF parameter (0.2477 (6)). Owing to poor agreement, the reflections (-7 5 5), (-7 5 7), (-8 4 - 5), (8 5 5), (2 0 0), (-8 - 5 5), (8 5 - 5), (8 - 5 5), (8 - 5 -5), (-8 - 5 -5), (-8 - 6 5), (-7 5 3), (-8 - 6 -5), (7 - 5 -3), (14 2 2) and (8 - 6 5) were omitted from the final cycles of refinement. All the H atoms were positioned geometrically and constrained to ride on their parent atom with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and with Uiso(H)=1.5Ueq for methyl H atoms and 1.2Ueq(C) for other H atoms.

Structure description top

The background to the biology and related structure of thiazepin derivatives, has been described recently (Bakthadoss et al., 2013). In view of this biological importance, the crystal structure of the title compound has been carried out and the results are presented here.

Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The seven membered thiazepine ring (N1/S1/C1/C2/C7/C8/C9) adopts slightly distorted twist-boat conformation as indicated by puckering parameters (Cremer & Pople, 1975): QT = 0.9884 (11) Å, φ2 = 359.3 (1)° and φ3 = 356.5 (4)°. The dihedral angle between the benzothiazepin ring system and the benzene ring is 60.3 (1)°. The atom O1 deviates by -0.895 (1) Å from the least-squares plane of the thiazepin ring. The sum of angles at N1 atom of the thiazepin ring (359.9°) is in accordance with sp2 hybridization. The geometric parameters of the title molecule agree well with those reported for a similar structure (Bakthadoss et al., 2013).

In the crystal, molecules are linked by two pairs of inversion-related N1—H1A···O1 and C18—H18B···O3 hydrogen bonds, generating alternate R22(8) and R22(6) ring motifs, respectively, resulting in a zigzag supramolecular chain running along the c axis. These chains stack along the a axis by S1···C4v = 3.424 (2) Å (Symmetry code:(v) = 1/2 - x, -1/2 + y, z) short contacts (Fig. 2 and Table 1). A three-dimensional supramolecular network is consolidated by C4—H4···Cg1iii (symmetry code: (iii) = 1/2 - x, 1/2 - y, 1/2 + z) and C10—H10B···Cg2iv (symmetry code: (iv) = x, -y, -1/2 + z) hydrogen bonds and Cg1—Cg1vi = 3.815 (1) Å (symmetry code: (vi) = -x, y, 3/2 - z) interactions (Fig. 3 and Table 1; Cg1 and Cg2 are the centroids of the C11–C16 and C2–C7 benzene rings, respectively).

For background to the biology of thiazepin derivatives and for a related structure, see: Bakthadoss et al. (2013). For ring-puckering parameters, see: Cremer & Pople (1975).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing displacement ellipsoids at the 30% probability level. H atoms are presented as a small spheres of arbitrary radii.
[Figure 2] Fig. 2. A view of the supramolecular chain showing N—H···O (red dotted lines) and C—H···O (blue dotted lines) hydrogen bonds. The chains stack along the the a axis via S···C (greeen dotted lines) short contacts.
[Figure 3] Fig. 3. View of three-dimensional supramolecular network down the c axis. The N—H···O, C—H···O, S···C, C—H···π and ππ interactions are shown as red, blue, green, orange and purple dotted lines, respectively. Cg1 and Cg2 are the centroids of the C11–C16 and C2–C7 benzene rings, respectively.
(Z)-3-(3,4-Dimethoxybenzyl)-1,5-benzothiazepin-4(5H)-one top
Crystal data top
C18H17NO3SF(000) = 1376
Mr = 327.39Dx = 1.354 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 2790 reflections
a = 19.966 (4) Åθ = 2.2–24.9°
b = 10.355 (2) ŵ = 0.22 mm1
c = 15.536 (3) ÅT = 293 K
V = 3212.0 (11) Å3Block, colourless
Z = 80.35 × 0.20 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer
13227 independent reflections
Radiation source: fine-focus sealed tube8413 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
Detector resolution: 10.0 pixels mm-1θmax = 24.9°, θmin = 2.2°
ω scansh = 2323
Absorption correction: multi-scan
(TWINABS; Sheldrick, 1997)
k = 129
Tmin = 0.927, Tmax = 0.968l = 1818
13227 measured reflections
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0582P)2]
where P = (Fo2 + 2Fc2)/3
13227 reflections(Δ/σ)max = 0.001
211 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C18H17NO3SV = 3212.0 (11) Å3
Mr = 327.39Z = 8
Orthorhombic, PbcnMo Kα radiation
a = 19.966 (4) ŵ = 0.22 mm1
b = 10.355 (2) ÅT = 293 K
c = 15.536 (3) Å0.35 × 0.20 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer
13227 independent reflections
Absorption correction: multi-scan
(TWINABS; Sheldrick, 1997)
8413 reflections with I > 2σ(I)
Tmin = 0.927, Tmax = 0.968Rint = 0.066
13227 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.175H-atom parameters constrained
S = 1.02Δρmax = 0.25 e Å3
13227 reflectionsΔρmin = 0.33 e Å3
211 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
C20.21158 (10)0.01584 (18)1.02679 (11)0.0320 (5)
C30.26554 (10)0.0619 (2)1.07376 (13)0.0401 (5)
H30.30720.02251.06830.048*
C40.25791 (10)0.1650 (2)1.12822 (13)0.0434 (6)
H40.29390.19351.16110.052*
C50.19688 (11)0.2264 (2)1.13416 (12)0.0405 (5)
H50.19210.29781.17000.049*
C60.14302 (10)0.18270 (19)1.08740 (11)0.0339 (5)
H60.10200.22491.09130.041*
C70.14978 (9)0.07580 (18)1.03449 (10)0.0265 (4)
C80.07914 (10)0.00895 (17)0.91369 (11)0.0300 (5)
C90.13353 (9)0.00907 (17)0.84820 (11)0.0277 (5)
C10.19328 (11)0.05969 (19)0.86307 (11)0.0359 (5)
H10.22300.06220.81700.043*
C100.11450 (10)0.04089 (18)0.76116 (11)0.0332 (5)
H10A0.07350.00160.74320.040*
H10B0.14930.01700.72060.040*
C110.10408 (8)0.18544 (17)0.75624 (10)0.0267 (4)
C120.12408 (10)0.2698 (2)0.81859 (11)0.0369 (5)
H120.14400.23840.86850.044*
C130.11523 (10)0.4015 (2)0.80865 (12)0.0406 (5)
H130.12860.45740.85220.049*
C140.08704 (10)0.45013 (18)0.73534 (12)0.0345 (5)
C150.06728 (9)0.36546 (19)0.67025 (11)0.0305 (5)
C160.07503 (9)0.23488 (19)0.68158 (10)0.0298 (5)
H160.06070.17850.63880.036*
C180.02274 (13)0.3361 (2)0.52964 (13)0.0661 (8)
H18A0.06160.29020.50990.099*
H18B0.00420.38520.48300.099*
H18C0.01000.27560.55020.099*
C170.08134 (13)0.6638 (2)0.78994 (14)0.0715 (8)
H17A0.05360.63250.83590.107*
H17B0.06650.74830.77300.107*
H17C0.12700.66840.80910.107*
N10.09093 (8)0.02648 (15)0.99504 (9)0.0325 (4)
H1A0.05730.01801.02910.039*
O10.02201 (7)0.04165 (14)0.89186 (8)0.0423 (4)
O30.04118 (7)0.42072 (13)0.59744 (8)0.0462 (4)
O20.07680 (8)0.57865 (13)0.71876 (9)0.0498 (4)
S10.22192 (3)0.12256 (6)0.96130 (3)0.04692 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0340 (13)0.0353 (12)0.0267 (10)0.0018 (10)0.0032 (9)0.0069 (9)
C30.0285 (13)0.0482 (15)0.0437 (12)0.0032 (10)0.0051 (9)0.0068 (11)
C40.0369 (15)0.0530 (15)0.0404 (12)0.0140 (12)0.0120 (10)0.0064 (11)
C50.0447 (14)0.0402 (13)0.0366 (11)0.0090 (11)0.0044 (10)0.0018 (10)
C60.0347 (13)0.0359 (13)0.0311 (10)0.0005 (10)0.0000 (9)0.0014 (9)
C70.0256 (12)0.0326 (12)0.0214 (9)0.0028 (9)0.0011 (8)0.0067 (9)
C80.0302 (13)0.0278 (12)0.0320 (10)0.0017 (9)0.0025 (9)0.0044 (9)
C90.0310 (12)0.0249 (11)0.0271 (9)0.0008 (9)0.0016 (8)0.0015 (8)
C10.0391 (14)0.0386 (13)0.0300 (10)0.0034 (10)0.0048 (9)0.0031 (9)
C100.0394 (13)0.0351 (12)0.0252 (9)0.0004 (9)0.0006 (8)0.0022 (9)
C110.0263 (12)0.0297 (11)0.0242 (9)0.0046 (9)0.0029 (8)0.0008 (9)
C120.0463 (14)0.0395 (13)0.0248 (10)0.0052 (11)0.0030 (9)0.0008 (9)
C130.0524 (15)0.0357 (14)0.0336 (11)0.0129 (11)0.0002 (10)0.0083 (10)
C140.0406 (14)0.0246 (12)0.0384 (11)0.0057 (9)0.0126 (10)0.0006 (10)
C150.0324 (13)0.0324 (12)0.0265 (10)0.0009 (9)0.0052 (8)0.0046 (9)
C160.0319 (13)0.0310 (12)0.0263 (10)0.0039 (9)0.0006 (8)0.0034 (9)
C180.111 (2)0.0510 (16)0.0358 (13)0.0186 (15)0.0196 (13)0.0014 (11)
C170.118 (2)0.0342 (15)0.0621 (16)0.0121 (15)0.0208 (15)0.0165 (13)
N10.0229 (10)0.0474 (11)0.0273 (8)0.0062 (8)0.0031 (7)0.0024 (8)
O10.0294 (9)0.0628 (10)0.0346 (7)0.0108 (7)0.0031 (6)0.0053 (7)
O30.0675 (11)0.0373 (9)0.0338 (8)0.0099 (7)0.0051 (7)0.0047 (7)
O20.0797 (12)0.0244 (8)0.0452 (8)0.0014 (8)0.0113 (8)0.0036 (7)
S10.0543 (4)0.0454 (4)0.0411 (3)0.0223 (3)0.0086 (3)0.0000 (3)
Geometric parameters (Å, º) top
C2—C31.386 (3)C10—H10B0.9700
C2—C71.386 (2)C11—C121.364 (2)
C2—S11.770 (2)C11—C161.394 (2)
C3—C41.371 (3)C12—C131.383 (3)
C3—H30.9300C12—H120.9300
C4—C51.377 (3)C13—C141.367 (3)
C4—H40.9300C13—H130.9300
C5—C61.374 (3)C14—O21.371 (2)
C5—H50.9300C14—C151.395 (3)
C6—C71.385 (3)C15—O31.370 (2)
C6—H60.9300C15—C161.372 (3)
C7—N11.420 (2)C16—H160.9300
C8—O11.237 (2)C18—O31.419 (2)
C8—N11.337 (2)C18—H18A0.9600
C8—C91.488 (3)C18—H18B0.9600
C9—C11.323 (3)C18—H18C0.9600
C9—C101.497 (2)C17—O21.417 (2)
C1—S11.7549 (19)C17—H17A0.9600
C1—H10.9300C17—H17B0.9600
C10—C111.513 (2)C17—H17C0.9600
C10—H10A0.9700N1—H1A0.8600
C3—C2—C7119.50 (18)C16—C11—C10117.55 (16)
C3—C2—S1119.38 (16)C11—C12—C13120.97 (18)
C7—C2—S1121.07 (14)C11—C12—H12119.5
C4—C3—C2120.44 (19)C13—C12—H12119.5
C4—C3—H3119.8C14—C13—C12120.58 (18)
C2—C3—H3119.8C14—C13—H13119.7
C3—C4—C5119.93 (19)C12—C13—H13119.7
C3—C4—H4120.0C13—C14—O2125.16 (17)
C5—C4—H4120.0C13—C14—C15119.27 (18)
C6—C5—C4120.3 (2)O2—C14—C15115.57 (17)
C6—C5—H5119.8O3—C15—C16124.07 (17)
C4—C5—H5119.8O3—C15—C14116.31 (17)
C5—C6—C7120.03 (19)C16—C15—C14119.61 (17)
C5—C6—H6120.0C15—C16—C11121.03 (17)
C7—C6—H6120.0C15—C16—H16119.5
C6—C7—C2119.72 (17)C11—C16—H16119.5
C6—C7—N1117.57 (17)O3—C18—H18A109.5
C2—C7—N1122.54 (17)O3—C18—H18B109.5
O1—C8—N1119.77 (17)H18A—C18—H18B109.5
O1—C8—C9119.02 (17)O3—C18—H18C109.5
N1—C8—C9121.21 (18)H18A—C18—H18C109.5
C1—C9—C8122.60 (17)H18B—C18—H18C109.5
C1—C9—C10121.56 (17)O2—C17—H17A109.5
C8—C9—C10115.60 (16)O2—C17—H17B109.5
C9—C1—S1126.33 (15)H17A—C17—H17B109.5
C9—C1—H1116.8O2—C17—H17C109.5
S1—C1—H1116.8H17A—C17—H17C109.5
C9—C10—C11114.99 (15)H17B—C17—H17C109.5
C9—C10—H10A108.5C8—N1—C7130.72 (16)
C11—C10—H10A108.5C8—N1—H1A114.6
C9—C10—H10B108.5C7—N1—H1A114.6
C11—C10—H10B108.5C15—O3—C18116.96 (16)
H10A—C10—H10B107.5C14—O2—C17116.60 (16)
C12—C11—C16118.50 (17)C1—S1—C299.30 (9)
C12—C11—C10123.88 (16)
C7—C2—C3—C40.7 (3)C11—C12—C13—C141.0 (3)
S1—C2—C3—C4176.75 (15)C12—C13—C14—O2179.20 (17)
C2—C3—C4—C52.3 (3)C12—C13—C14—C150.1 (3)
C3—C4—C5—C61.7 (3)C13—C14—C15—O3178.15 (17)
C4—C5—C6—C70.5 (3)O2—C14—C15—O31.0 (2)
C5—C6—C7—C22.1 (3)C13—C14—C15—C161.5 (3)
C5—C6—C7—N1173.30 (16)O2—C14—C15—C16179.36 (16)
C3—C2—C7—C61.5 (3)O3—C15—C16—C11177.80 (17)
S1—C2—C7—C6178.92 (13)C14—C15—C16—C111.8 (3)
C3—C2—C7—N1173.68 (16)C12—C11—C16—C150.7 (3)
S1—C2—C7—N13.7 (2)C10—C11—C16—C15176.41 (16)
O1—C8—C9—C1133.7 (2)O1—C8—N1—C7175.13 (18)
N1—C8—C9—C146.7 (3)C9—C8—N1—C74.5 (3)
O1—C8—C9—C1040.8 (2)C6—C7—N1—C8133.3 (2)
N1—C8—C9—C10138.76 (18)C2—C7—N1—C851.4 (3)
C8—C9—C1—S15.3 (3)C16—C15—O3—C181.4 (3)
C10—C9—C1—S1179.56 (14)C14—C15—O3—C18178.15 (18)
C1—C9—C10—C11113.1 (2)C13—C14—O2—C1715.3 (3)
C8—C9—C10—C1172.2 (2)C15—C14—O2—C17165.61 (18)
C9—C10—C11—C1214.1 (3)C9—C1—S1—C258.0 (2)
C9—C10—C11—C16168.94 (16)C3—C2—S1—C1125.91 (16)
C16—C11—C12—C130.7 (3)C7—C2—S1—C156.68 (17)
C10—C11—C12—C13177.59 (18)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C11–C16 and C2–C7 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.022.863 (2)167
C18—H18B···O3ii0.962.533.445 (3)159
C4—H4···Cg1iii0.932.573.450 (2)158
C10—H10B···Cg2iv0.972.823.725 (2)155
Symmetry codes: (i) x, y, z+2; (ii) x, y+1, z+1; (iii) x+1/2, y+1/2, z+1/2; (iv) x, y, z3/2.

Experimental details

Crystal data
Chemical formulaC18H17NO3S
Mr327.39
Crystal system, space groupOrthorhombic, Pbcn
Temperature (K)293
a, b, c (Å)19.966 (4), 10.355 (2), 15.536 (3)
V3)3212.0 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.35 × 0.20 × 0.15
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(TWINABS; Sheldrick, 1997)
Tmin, Tmax0.927, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections
13227, 13227, 8413
Rint0.066
(sin θ/λ)max1)0.592
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.175, 1.02
No. of reflections13227
No. of parameters211
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.33

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C11–C16 and C2–C7 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.022.863 (2)167
C18—H18B···O3ii0.962.533.445 (3)159
C4—H4···Cg1iii0.932.573.450 (2)158
C10—H10B···Cg2iv0.972.823.725 (2)155
Symmetry codes: (i) x, y, z+2; (ii) x, y+1, z+1; (iii) x+1/2, y+1/2, z+1/2; (iv) x, y, z3/2.
 

Footnotes

Additional correspondence author, e-mail: bhakthadoss@yahoo.com.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

First citationBakthadoss, M., Selvakumar, R., Manikandan, N. & Murugavel, S. (2013). Acta Cryst. E69, o562–o563.  CSD CrossRef CAS IUCr Journals Google Scholar
First citationBruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (1997). TWINABS. 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
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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