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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 1| January 2015| Pages o21-o22
https://doi.org/10.1107/S2056989014026267

Crystal structure of (Z)-3-(4-meth­­oxy­benzyl­­idene)-2,3-di­hydro­benzo[b][1,4]thia­zepin-4(5H)-one

V. Vinayagam,a J. Mohan Raj,b S. Murugavel,c* R. Selvakumara and M. Bakthadossa,d*

aDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India, bDepartment of Physics, C. Abdul Hakeem College of Engineering & Technology, Melvisharam, Vellore 632 509, India, cDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and dDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India
*Correspondence e-mail: smurugavel27@gmail.com, bhakthadoss@yahoo.com

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 26 November 2014; accepted 30 November 2014; online 1 January 2015)

In the title compound, C17H15NO2S, the two C atoms linking the S and carbonyl C atoms of the seven-membered thia­zepine ring are disordered over two sites, with occupancies of 0.511 (4) and 0.489 (4); both disorder components adopt distorted twist-boat conformations. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds link inverted-related mol­ecules into dimers, incorporating R12(6) and R22(8) ring motifs; the acceptor carbonyl O atom is bifurcated. These dimers are further linked by C—H⋯O hydrogen bonds, forming supra­molecular tapes running along the a axis.

CCDC reference: 1036763

Similar articles

1. Related literature

For the pharmaceutical properties of thia­zepin derivatives, see: Lončar-Tomascovic et al. (2000[Lončar-Tomašcović, L., Šarac-Arneri, R., Hergold-Brundić, A., Nagl, A., Mintas, M. & Sandström, J. (2000). HCA, 83, 479-494.]); Rajsner et al. (1971[Rajsner, M., Protiva, M. & Metysova, J. (1971). Czech. Patent Appl. CS 143737.]); Metys & Metysová (1965[Metys, J. & Metysová, J. (1965). Acta Biol. Med. Ger. 15, 871-873.]). For related structures, see: Lakshmanan et al. (2012[Lakshmanan, D., Murugavel, S., Selvakumar, R. & Bakthadoss, M. (2012). Acta Cryst. E68, o2130.]); Selvakumar et al. (2012[Selvakumar, R., Bakthadoss, M., Lakshmanan, D. & Murugavel, S. (2012). Acta Cryst. E68, o2126.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C17H15NO2S

  • Mr = 297.36

  • Monoclinic, C 2/c

  • a = 21.434 (5) Å

  • b = 5.715 (4) Å

  • c = 23.870 (5) Å

  • β = 101.091 (4)°

  • V = 2869 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.23 mm−1

  • T = 293 K

  • 0.30 × 0.30 × 0.25 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.934, Tmax = 0.944

  • 17286 measured reflections

  • 4099 independent reflections

  • 2744 reflections with I > 2σ(I)

  • Rint = 0.028

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.139

  • S = 1.03

  • 4099 reflections

  • 210 parameters

  • 4 restraints

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.86 2.07 2.9291 (18) 177
C6—H6⋯O1i 0.93 2.45 3.263 (3) 146
C1B—H1C⋯O1ii 0.97 2.52 3.377 (4) 147
Symmetry codes: (i) -x, -y, -z; (ii) x, y+1, z.

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

CCDC reference: 1036763

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989014026267/tk5350sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989014026267/tk5350Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989014026267/tk5350Isup3.cml

checkCIF report


Structural commentary top

The title compound is used as an inter­mediate for the synthesis of dosulepin, which is an anti­depressant of the tricyclic family. Dosulepin prevents reabsorbing of serotonin and noradrenaline in the brain, helps to prolong the mood lightening effect of any released noradrenaline and serotonin, thus relieving depression. Dibenzo[c,e]thia­zepin derivatives exhibit chiroptical properties (Tomascovic et al., 2000). Dibenzo[b,e]thia­zepin-5,5-dioxide derivatives possess anti­histaminic and anti­allergenic activities (Rajsner et al., 1971). Benzene thia­zepin derivatives are identified as a type of effective anti­histaminic compounds (Metys et al., 1965). 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 geometric parameters of the title molecule agree well with those reported for similar structures (Selvakumar et al.., 2012; Lakshmanan et al., 2012). The sum of angles at N1 atom of the thia­zepin ring (359.9°) is in accordance with sp2 hybridization. Both the major and minor conformers of the disorderd thia­zepine ring adopt distorted twist-boat conformations.

In the crystal, inter­molecular bifurcated acceptor N1—H1···O1i and C6—H6···O1i (Table 1) hydrogen bonds link inverted-related molecules into dimers, incorporating R12(6) and R22(8) ring motifs. These dimers are further linked by C1B—H1C···O1ii (Table 1) hydrogen bonds forming supra­molecular tapes running along the a axis (Fig. 2).

Synthesis and crystallization top

A mixture of (Z)-methyl 2-(bromo­methyl)-3-(4-meth­oxy­phenyl)­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. It was then concentrated to successfully provide the crude final product ((Z)-3-(4-meth­oxy­benzyl­idene)-2,3-di­hydro­benzo[b][1,4] thia­zepin-4(5H)-one). This was purified by column chromatography on silica gel with ethyl­acetate/hexane 1:19 as eluent to afford the title compound in good yield (47 %). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of its ethyl­acetate solution at room temperature.

Refinement top

Atoms C1 and C9 of the thia­zepine ring are disordered over two positions (C1A/C1B and C9A/C9B) with refined occupancies of 0.511 (4) and 0.489 (4). The corresponding bond distances involving the disorderd atoms were restrained to be equal. H atoms were positioned geometrically, (C—H = 0.93–0.97 Å and N—H = 0.86 Å) constrained to ride on their parent atom, with Uiso(H)=1.5Ueq for methyl H atoms and 1.2Ueq(C) for other H atoms.

Related literature top

For the pharmaceutical properties of thiazepin derivatives, see: Lončar-Tomascovic et al. (2000); Rajsner et al. (1971); Metys & Metysová (1965). For related structures, see: Lakshmanan et al. (2012); Selvakumar et al. (2012).

Structure description top

The title compound is used as an inter­mediate for the synthesis of dosulepin, which is an anti­depressant of the tricyclic family. Dosulepin prevents reabsorbing of serotonin and noradrenaline in the brain, helps to prolong the mood lightening effect of any released noradrenaline and serotonin, thus relieving depression. Dibenzo[c,e]thia­zepin derivatives exhibit chiroptical properties (Tomascovic et al., 2000). Dibenzo[b,e]thia­zepin-5,5-dioxide derivatives possess anti­histaminic and anti­allergenic activities (Rajsner et al., 1971). Benzene thia­zepin derivatives are identified as a type of effective anti­histaminic compounds (Metys et al., 1965). 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 geometric parameters of the title molecule agree well with those reported for similar structures (Selvakumar et al.., 2012; Lakshmanan et al., 2012). The sum of angles at N1 atom of the thia­zepin ring (359.9°) is in accordance with sp2 hybridization. Both the major and minor conformers of the disorderd thia­zepine ring adopt distorted twist-boat conformations.

In the crystal, inter­molecular bifurcated acceptor N1—H1···O1i and C6—H6···O1i (Table 1) hydrogen bonds link inverted-related molecules into dimers, incorporating R12(6) and R22(8) ring motifs. These dimers are further linked by C1B—H1C···O1ii (Table 1) hydrogen bonds forming supra­molecular tapes running along the a axis (Fig. 2).

For the pharmaceutical properties of thiazepin derivatives, see: Lončar-Tomascovic et al. (2000); Rajsner et al. (1971); Metys & Metysová (1965). For related structures, see: Lakshmanan et al. (2012); Selvakumar et al. (2012).

Synthesis and crystallization top

A mixture of (Z)-methyl 2-(bromo­methyl)-3-(4-meth­oxy­phenyl)­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. It was then concentrated to successfully provide the crude final product ((Z)-3-(4-meth­oxy­benzyl­idene)-2,3-di­hydro­benzo[b][1,4] thia­zepin-4(5H)-one). This was purified by column chromatography on silica gel with ethyl­acetate/hexane 1:19 as eluent to afford the title compound in good yield (47 %). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of its ethyl­acetate solution at room temperature.

Refinement details top

Atoms C1 and C9 of the thia­zepine ring are disordered over two positions (C1A/C1B and C9A/C9B) with refined occupancies of 0.511 (4) and 0.489 (4). The corresponding bond distances involving the disorderd atoms were restrained to be equal. H atoms were positioned geometrically, (C—H = 0.93–0.97 Å and N—H = 0.86 Å) constrained to ride on their parent atom, with Uiso(H)=1.5Ueq for methyl H atoms and 1.2Ueq(C) for other H atoms.

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. Supramolecular tape formation in the crystal packing of the title compound whereby bifurcated hydrogen bonds link inverted molecules into dimers sustained by N—H···O and C—H···O (red dashed lines) contacts are linked via C—H···O contacts (blue dashed lines) along a axis. [Symmetry code: (i) -x, -y, -z; (ii) x, 1+y, z].
(Z)-3-(4-Methoxybenzylidene)-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one top
Crystal data top
C17H15NO2SF(000) = 1248
Mr = 297.36Dx = 1.377 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4132 reflections
a = 21.434 (5) Åθ = 1.7–29.9°
b = 5.715 (4) ŵ = 0.23 mm−1
c = 23.870 (5) ÅT = 293 K
β = 101.091 (4)°Block, colourless
V = 2869 (2) Å30.30 × 0.30 × 0.25 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer		4099 independent reflections
Radiation source: fine-focus sealed tube2744 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 10.0 pixels mm-1θmax = 29.9°, θmin = 1.7°
ω scansh = −30→24
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −7→8
Tmin = 0.934, Tmax = 0.944l = −33→32
17286 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0647P)2 + 1.1615P]
where P = (Fo2 + 2Fc2)/3
4099 reflections(Δ/σ)max < 0.001
210 parametersΔρmax = 0.25 e Å−3
4 restraintsΔρmin = −0.34 e Å−3
Crystal data top
C17H15NO2SV = 2869 (2) Å3
Mr = 297.36Z = 8
Monoclinic, C2/cMo Kα radiation
a = 21.434 (5) ŵ = 0.23 mm−1
b = 5.715 (4) ÅT = 293 K
c = 23.870 (5) Å0.30 × 0.30 × 0.25 mm
β = 101.091 (4)°
Data collection top
Bruker APEXII CCD
diffractometer		4099 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2744 reflections with I > 2σ(I)
Tmin = 0.934, Tmax = 0.944Rint = 0.028
17286 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0454 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.03Δρmax = 0.25 e Å−3
4099 reflectionsΔρmin = −0.34 e Å−3
210 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 > 2sigma(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*/UeqOcc. (<1)
C2−0.05513 (8)0.5769 (3)0.10567 (7)0.0516 (4)
C3−0.09963 (11)0.7568 (3)0.10107 (9)0.0689 (5)
H3−0.10010.85120.13270.083*
C4−0.14266 (12)0.8004 (4)0.05193 (10)0.0790 (6)
H4−0.17180.92190.05030.095*
C5−0.14211 (10)0.6629 (4)0.00527 (10)0.0722 (5)
H5−0.17080.6906−0.02860.087*
C6−0.09941 (10)0.4851 (4)0.00854 (9)0.0691 (5)
H6−0.09960.3927−0.02360.083*
C7−0.05515 (8)0.4357 (3)0.05837 (8)0.0525 (4)
C80.03347 (9)0.1194 (3)0.08459 (7)0.0549 (4)
C100.10676 (9)0.0681 (3)0.17287 (7)0.0528 (4)
H10A0.1284−0.01300.14870.063*0.489 (4)
H10B0.1093−0.07850.15660.063*0.511 (4)
C110.14272 (8)0.0921 (3)0.23129 (7)0.0474 (4)
C120.13743 (8)0.2801 (3)0.26731 (7)0.0534 (4)
H120.10740.39570.25490.064*
C130.17552 (8)0.2999 (3)0.32082 (7)0.0525 (4)
H130.17100.42760.34390.063*
C140.22010 (8)0.1302 (3)0.33987 (7)0.0492 (4)
C150.22513 (8)−0.0627 (3)0.30585 (8)0.0551 (4)
H150.2542−0.18060.31900.066*
C160.18736 (8)−0.0793 (3)0.25292 (8)0.0533 (4)
H160.1915−0.20930.23050.064*
C170.26254 (13)0.3437 (5)0.42387 (10)0.0895 (7)
H17A0.27160.47520.40170.134*
H17B0.29500.33050.45760.134*
H17C0.22200.36560.43460.134*
N1−0.01563 (7)0.2418 (3)0.05307 (6)0.0610 (4)
H1−0.02580.18260.01940.073*
O10.05465 (6)−0.0461 (2)0.06174 (5)0.0605 (3)
O20.26115 (6)0.1372 (2)0.39107 (6)0.0691 (4)
S1−0.00374 (3)0.55138 (8)0.17212 (2)0.06381 (18)
C1A0.00694 (16)0.2393 (5)0.18212 (13)0.0438 (8)0.489 (4)
H1A0.02220.20800.22240.053*0.489 (4)
H1B−0.03400.16290.17100.053*0.489 (4)
C9A0.05207 (17)0.1363 (7)0.14902 (14)0.0425 (8)0.489 (4)
C1B0.06528 (16)0.4832 (6)0.14859 (14)0.0529 (9)0.511 (4)
H1C0.06610.56690.11340.063*0.511 (4)
H1D0.10160.53380.17680.063*0.511 (4)
C9B0.07040 (18)0.2265 (6)0.13852 (15)0.0467 (8)0.511 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0612 (10)0.0418 (8)0.0559 (9)−0.0078 (7)0.0218 (8)−0.0015 (7)
C30.0945 (15)0.0501 (10)0.0679 (12)0.0085 (10)0.0301 (11)0.0005 (9)
C40.0937 (16)0.0612 (12)0.0861 (15)0.0218 (11)0.0275 (13)0.0105 (11)
C50.0695 (12)0.0685 (13)0.0761 (13)0.0072 (10)0.0079 (10)0.0050 (11)
C60.0674 (12)0.0676 (12)0.0677 (12)0.0064 (10)0.0018 (9)−0.0141 (10)
C70.0505 (9)0.0505 (9)0.0570 (9)−0.0039 (7)0.0117 (7)−0.0085 (7)
C80.0606 (10)0.0570 (10)0.0470 (9)0.0012 (8)0.0105 (8)−0.0085 (7)
C100.0680 (11)0.0419 (8)0.0494 (9)−0.0073 (8)0.0134 (8)−0.0044 (7)
C110.0530 (9)0.0431 (8)0.0481 (8)−0.0056 (7)0.0147 (7)−0.0008 (6)
C120.0564 (10)0.0456 (9)0.0562 (9)0.0089 (7)0.0060 (8)−0.0005 (7)
C130.0556 (10)0.0487 (9)0.0530 (9)0.0055 (7)0.0097 (7)−0.0071 (7)
C140.0464 (8)0.0509 (9)0.0514 (9)0.0014 (7)0.0122 (7)0.0047 (7)
C150.0538 (10)0.0464 (9)0.0658 (11)0.0106 (7)0.0135 (8)0.0047 (8)
C160.0601 (10)0.0418 (8)0.0614 (10)0.0026 (7)0.0200 (8)−0.0054 (7)
C170.1079 (18)0.0866 (16)0.0624 (12)0.0135 (14)−0.0125 (12)−0.0123 (12)
N10.0660 (9)0.0634 (9)0.0499 (8)0.0091 (7)0.0020 (7)−0.0183 (7)
O10.0781 (8)0.0546 (7)0.0481 (7)0.0079 (6)0.0104 (6)−0.0085 (5)
O20.0680 (8)0.0720 (9)0.0597 (8)0.0116 (7)−0.0064 (6)0.0002 (7)
S10.0906 (4)0.0514 (3)0.0512 (3)−0.0002 (2)0.0179 (2)−0.00693 (19)
C1A0.0543 (18)0.0415 (16)0.0383 (15)−0.0025 (13)0.0156 (13)−0.0022 (12)
C9A0.048 (2)0.0385 (18)0.0434 (17)−0.0072 (15)0.0143 (15)−0.0046 (14)
C1B0.063 (2)0.0443 (17)0.0482 (17)−0.0116 (14)0.0023 (15)0.0032 (13)
C9B0.0474 (19)0.0451 (19)0.0477 (18)−0.0094 (15)0.0093 (15)−0.0068 (15)
Geometric parameters (Å, º) top
C2—C71.388 (2)C12—C131.382 (2)
C2—C31.392 (3)C12—H120.9300
C2—S11.7545 (19)C13—C141.376 (2)
C3—C41.368 (3)C13—H130.9300
C3—H30.9300C14—O21.362 (2)
C4—C51.365 (3)C14—C151.386 (2)
C4—H40.9300C15—C161.367 (2)
C5—C61.360 (3)C15—H150.9300
C5—H50.9300C16—H160.9300
C6—C71.400 (3)C17—O21.413 (3)
C6—H60.9300C17—H17A0.9600
C7—N11.415 (2)C17—H17B0.9600
C8—O11.222 (2)C17—H17C0.9600
C8—N11.363 (2)N1—H10.8600
C8—C9B1.505 (4)S1—C1B1.725 (3)
C8—C9A1.516 (4)S1—C1A1.808 (3)
C10—C9A1.262 (4)C1A—C9A1.484 (4)
C10—C9B1.361 (4)C1A—H1A0.9700
C10—C111.464 (2)C1A—H1B0.9700
C10—H10A0.9300C1B—C9B1.494 (4)
C10—H10B0.9300C1B—H1C0.9700
C11—C121.395 (2)C1B—H1D0.9700
C11—C161.397 (2)
C7—C2—C3118.18 (18)C12—C13—H13120.1
C7—C2—S1126.08 (14)O2—C14—C13124.28 (16)
C3—C2—S1115.74 (14)O2—C14—C15116.08 (15)
C4—C3—C2122.73 (19)C13—C14—C15119.64 (16)
C4—C3—H3118.6C16—C15—C14119.87 (15)
C2—C3—H3118.6C16—C15—H15120.1
C5—C4—C3119.0 (2)C14—C15—H15120.1
C5—C4—H4120.5C15—C16—C11122.34 (16)
C3—C4—H4120.5C15—C16—H16118.8
C6—C5—C4119.7 (2)C11—C16—H16118.8
C6—C5—H5120.2O2—C17—H17A109.5
C4—C5—H5120.2O2—C17—H17B109.5
C5—C6—C7122.6 (2)H17A—C17—H17B109.5
C5—C6—H6118.7O2—C17—H17C109.5
C7—C6—H6118.7H17A—C17—H17C109.5
C2—C7—C6117.89 (17)H17B—C17—H17C109.5
C2—C7—N1128.43 (17)C8—N1—C7139.85 (15)
C6—C7—N1113.67 (16)C8—N1—H1110.1
O1—C8—N1117.68 (15)C7—N1—H1110.1
O1—C8—C9B121.1 (2)C14—O2—C17117.57 (15)
N1—C8—C9B119.10 (19)C1B—S1—C298.80 (12)
O1—C8—C9A117.03 (19)C1B—S1—C1A74.06 (15)
N1—C8—C9A123.48 (18)C2—S1—C1A104.06 (12)
C9B—C8—C9A27.63 (14)C9A—C1A—S1113.6 (2)
C9A—C10—C9B31.63 (17)C9A—C1A—H1A108.8
C9A—C10—C11132.4 (2)S1—C1A—H1A108.8
C9B—C10—C11130.31 (19)C9A—C1A—H1B108.8
C9A—C10—H10A113.8S1—C1A—H1B108.8
C9B—C10—H10A104.7H1A—C1A—H1B107.7
C11—C10—H10A113.8C10—C9A—C1A121.8 (3)
C9A—C10—H10B102.4C10—C9A—C8118.6 (2)
C9B—C10—H10B114.8C1A—C9A—C8119.6 (3)
C11—C10—H10B114.9C9B—C1B—S1111.6 (2)
H10A—C10—H10B38.2C9B—C1B—H1C109.3
C12—C11—C16116.35 (16)S1—C1B—H1C109.3
C12—C11—C10124.67 (15)C9B—C1B—H1D109.3
C16—C11—C10118.94 (15)S1—C1B—H1D109.3
C13—C12—C11121.95 (16)H1C—C1B—H1D108.0
C13—C12—H12119.0C10—C9B—C1B127.4 (3)
C11—C12—H12119.0C10—C9B—C8113.0 (2)
C14—C13—C12119.80 (16)C1B—C9B—C8119.6 (3)
C14—C13—H13120.1
C7—C2—C3—C4−0.6 (3)C7—C2—S1—C1B39.04 (18)
S1—C2—C3—C4179.50 (17)C3—C2—S1—C1B−141.03 (17)
C2—C3—C4—C5−0.1 (3)C7—C2—S1—C1A−36.62 (18)
C3—C4—C5—C60.5 (3)C3—C2—S1—C1A143.31 (16)
C4—C5—C6—C7−0.1 (4)C1B—S1—C1A—C9A−17.3 (2)
C3—C2—C7—C60.9 (3)C2—S1—C1A—C9A78.0 (2)
S1—C2—C7—C6−179.14 (14)C9B—C10—C9A—C1A−109.5 (6)
C3—C2—C7—N1−178.87 (18)C11—C10—C9A—C1A−8.6 (6)
S1—C2—C7—N11.1 (3)C9B—C10—C9A—C868.3 (4)
C5—C6—C7—C2−0.6 (3)C11—C10—C9A—C8169.3 (2)
C5—C6—C7—N1179.2 (2)S1—C1A—C9A—C10107.7 (4)
C9A—C10—C11—C12−30.8 (4)S1—C1A—C9A—C8−70.1 (4)
C9B—C10—C11—C1211.7 (4)O1—C8—C9A—C1034.1 (4)
C9A—C10—C11—C16151.4 (3)N1—C8—C9A—C10−161.6 (3)
C9B—C10—C11—C16−166.1 (3)C9B—C8—C9A—C10−71.9 (4)
C16—C11—C12—C131.9 (2)O1—C8—C9A—C1A−148.0 (3)
C10—C11—C12—C13−175.93 (16)N1—C8—C9A—C1A16.3 (4)
C11—C12—C13—C14−0.2 (3)C9B—C8—C9A—C1A105.9 (6)
C12—C13—C14—O2177.88 (16)C2—S1—C1B—C9B−85.8 (2)
C12—C13—C14—C15−1.9 (3)C1A—S1—C1B—C9B16.4 (2)
O2—C14—C15—C16−177.57 (15)C9A—C10—C9B—C1B118.0 (6)
C13—C14—C15—C162.2 (3)C11—C10—C9B—C1B10.1 (6)
C14—C15—C16—C11−0.4 (3)C9A—C10—C9B—C8−63.2 (4)
C12—C11—C16—C15−1.6 (2)C11—C10—C9B—C8−171.13 (19)
C10—C11—C16—C15176.40 (16)S1—C1B—C9B—C10−102.3 (4)
O1—C8—N1—C7−179.9 (2)S1—C1B—C9B—C879.0 (4)
C9B—C8—N1—C7−16.1 (4)O1—C8—C9B—C10−32.2 (4)
C9A—C8—N1—C715.9 (4)N1—C8—C9B—C10164.6 (2)
C2—C7—N1—C8−1.1 (4)C9A—C8—C9B—C1057.2 (4)
C6—C7—N1—C8179.1 (2)O1—C8—C9B—C1B146.6 (3)
C13—C14—O2—C17−7.0 (3)N1—C8—C9B—C1B−16.6 (4)
C15—C14—O2—C17172.7 (2)C9A—C8—C9B—C1B−123.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.072.9291 (18)177
C6—H6···O1i0.932.453.263 (3)146
C1B—H1C···O1ii0.972.523.377 (4)147
Symmetry codes: (i) −x, −y, −z; (ii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.072.9291 (18)177
C6—H6···O1i0.932.453.263 (3)146
C1B—H1C···O1ii0.972.523.377 (4)147
Symmetry codes: (i) −x, −y, −z; (ii) x, y+1, z.
 

Acknowledgements

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

References

First citationBruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationLakshmanan, D., Murugavel, S., Selvakumar, R. & Bakthadoss, M. (2012). Acta Cryst. E68, o2130.  CSD CrossRef IUCr Journals Google Scholar
 First citationLončar-Tomašcović, L., Šarac-Arneri, R., Hergold-Brundić, A., Nagl, A., Mintas, M. & Sandström, J. (2000). HCA, 83, 479–494.  Google Scholar
 First citationMetys, J. & Metysová, J. (1965). Acta Biol. Med. Ger. 15, 871–873.  CAS PubMed Web of Science Google Scholar
 First citationRajsner, M., Protiva, M. & Metysova, J. (1971). Czech. Patent Appl. CS 143737.  Google Scholar
 First citationSelvakumar, R., Bakthadoss, M., Lakshmanan, D. & Murugavel, S. (2012). Acta Cryst. E68, o2126.  CSD CrossRef IUCr Journals 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
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 71| Part 1| January 2015| Pages o21-o22
https://doi.org/10.1107/S2056989014026267
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