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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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

(Received 10 June 2012; accepted 12 June 2012; online 16 June 2012)

In the title compound, C16H12ClNOS, the seven-membered thia­zepine ring adopts a distorted twisted boat conformation. The dihedral angle between the least-squares planes of the 1,5-benzothia­zepine ring system and the benzene ring is 50.2 (1)°. In the crystal, pairs of N—H⋯O hydrogen bonds link centrosymmetrically related mol­ecules into dimers, generating R22(8) ring motifs. The crystal packing is further stabilized by ππ inter­actions [centroid–centroid distance = 3.763 (2) Å].

Related literature

For the pharmaceutical properties of thia­zepin derivatives, see: Tomascovic et al. (2000[Tomascovic, L. L., Arneri, R. S., Brundic, A. H., Nagl, A., Mintas, M. & Sandtrom, J. (2000). Helv. Chim. Acta, 83, 479-493.]); Rajsner et al. (1971[Rajsner, M., Protiva, M. & Metysova, J. (1971). Czech. Patent Appl. CS 143737.]); Metys et al. (1965[Metys, J., Metysova, J. & Votava, Z. (1965). Acta Biol. Med. Ger. 15, 871-873.]). For related structures, see: Sridevi et al. (2011[Sridevi, D., Bhaskaran, S., Usha, G., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o243.]); Sabari et al. (2011[Sabari, V., Jagadeesan, G., Selvakumar, R., Bakthadoss, M. & Aravindhan, S. (2011). Acta Cryst. E67, o3061.]); Selvakumar et al. (2012[Selvakumar, R., Bakthadoss, M., Lakshmanan, D. & Murugavel, S. (2012). Acta Cryst. E68, o2126.]). For ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12ClNOS

  • Mr = 301.78

  • Orthorhombic, P b c a

  • a = 9.0486 (3) Å

  • b = 9.4105 (3) Å

  • c = 33.4876 (10) Å

  • V = 2851.53 (16) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.41 mm−1

  • T = 293 K

  • 0.23 × 0.21 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.910, Tmax = 0.941

  • 14850 measured reflections

  • 3099 independent reflections

  • 2382 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.118

  • S = 1.03

  • 3099 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1i 0.86 2.07 2.854 (2) 151
Symmetry code: (i) -x, -y, -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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); 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 title compound is used as an intermediate for the synthesis of dosulepin, which is an anti-depressant 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. The dibenzo[c,e]thiazepin derivatives exhibit chiroptical properties (Tomascovic et al., 2000). Dibenzo[b,e]thiazepin-5,5-dioxide derivatives possess anti-histaminic and anti-allergenic activities (Rajsner et al., 1971). Benzene thiazepin derivatives are identified as a new type of effective anti-histaminic 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 the seven membered thiazepine ring (N1/S1/C1/C2/C7/C8/C9) to adopt a twisted-boat conformation as indicated by puckering parameters (Cremer & Pople, 1975) QT = 1.0015 (16) Å, θ2 = 74.1 (1)°, φ2 = 177.3 (1)° and φ3 = 177.6 (4)°. The dihedral angle between the benzothiazepin ring system and the benzene ring is 50.2 (1)°. The geometric parameters of the title molecule agree well with those reported for similar structures (Sridevi et al., 2011; Sabari et al., 2011).

In the crystal packing (Fig. 2), centrosymmetrically related molecules are linked by N1—H1···O1 hydrogen bonds into cyclic R22(8) dimers (Bernstein et al., 1995). The crystal packing (Fig. 3) is further stabilized by intermolecular ππ interactions with a CgCgi separation of 3.763 (1) Å [Cg is the centroid of the C2–C7 benzene ring, symmetry code as in Fig. 3].

Related literature top

For the pharmaceutical properties of thiazepin derivatives, see: Tomascovic et al. (2000); Rajsner et al. (1971); Metys et al. (1965). For related structures, see: Sridevi et al. (2011); Sabari et al. (2011); Selvakumar et al. (2012). . For ring-puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of (Z)-methyl 2-(bromomethyl)-3-(4-chlorophenyl)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 × 20 ml). The organic layer was washed with brine (2 × 20 ml) and dried over anhydrous sodium sulfate. The organic layer was concentrated, which successfully provided the crude final product. The final product was purified by column chromatography on silica gel to afford the title compound in good yield (43%).

Refinement top

H atoms were positioned geometrically, with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(N,C).

Structure description top

The title compound is used as an intermediate for the synthesis of dosulepin, which is an anti-depressant 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. The dibenzo[c,e]thiazepin derivatives exhibit chiroptical properties (Tomascovic et al., 2000). Dibenzo[b,e]thiazepin-5,5-dioxide derivatives possess anti-histaminic and anti-allergenic activities (Rajsner et al., 1971). Benzene thiazepin derivatives are identified as a new type of effective anti-histaminic 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 the seven membered thiazepine ring (N1/S1/C1/C2/C7/C8/C9) to adopt a twisted-boat conformation as indicated by puckering parameters (Cremer & Pople, 1975) QT = 1.0015 (16) Å, θ2 = 74.1 (1)°, φ2 = 177.3 (1)° and φ3 = 177.6 (4)°. The dihedral angle between the benzothiazepin ring system and the benzene ring is 50.2 (1)°. The geometric parameters of the title molecule agree well with those reported for similar structures (Sridevi et al., 2011; Sabari et al., 2011).

In the crystal packing (Fig. 2), centrosymmetrically related molecules are linked by N1—H1···O1 hydrogen bonds into cyclic R22(8) dimers (Bernstein et al., 1995). The crystal packing (Fig. 3) is further stabilized by intermolecular ππ interactions with a CgCgi separation of 3.763 (1) Å [Cg is the centroid of the C2–C7 benzene ring, symmetry code as in Fig. 3].

For the pharmaceutical properties of thiazepin derivatives, see: Tomascovic et al. (2000); Rajsner et al. (1971); Metys et al. (1965). For related structures, see: Sridevi et al. (2011); Sabari et al. (2011); Selvakumar et al. (2012). . For ring-puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

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 (Farrugia, 1997); 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. Part of the crystal structure of the title compound showing N—H···O intermolecular hydrogen bonds (dotted lines) generating an R22(8) centrosymmetric dimer [Symmetry code: (i) -x, -y, -z].
[Figure 3] Fig. 3. A view of a ππ interaction (dotted lines) in the crystal structure of the title compound. Cg denotes centroid of the C2–C7 benzene ring [Symmetry code: (i) -x, 1 - y, -z].
(Z)-3-(4-Chlorobenzyl)-1,5-benzothiazepin-4(5H)-one top
Crystal data top
C16H12ClNOSF(000) = 1248
Mr = 301.78Dx = 1.406 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3130 reflections
a = 9.0486 (3) Åθ = 2.4–27.0°
b = 9.4105 (3) ŵ = 0.41 mm1
c = 33.4876 (10) ÅT = 293 K
V = 2851.53 (16) Å3Block, colourless
Z = 80.23 × 0.21 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer
3099 independent reflections
Radiation source: fine-focus sealed tube2382 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 2.4°
ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1011
Tmin = 0.910, Tmax = 0.941l = 4229
14850 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.0432P)2 + 1.9074P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3099 reflectionsΔρmax = 0.35 e Å3
182 parametersΔρmin = 0.45 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0057 (6)
Crystal data top
C16H12ClNOSV = 2851.53 (16) Å3
Mr = 301.78Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 9.0486 (3) ŵ = 0.41 mm1
b = 9.4105 (3) ÅT = 293 K
c = 33.4876 (10) Å0.23 × 0.21 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer
3099 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2382 reflections with I > 2σ(I)
Tmin = 0.910, Tmax = 0.941Rint = 0.029
14850 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.03Δρmax = 0.35 e Å3
3099 reflectionsΔρmin = 0.45 e Å3
182 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
C10.0719 (3)0.1514 (2)0.12513 (6)0.0476 (5)
H1A0.06550.14660.15280.057*
C20.0392 (2)0.3707 (2)0.07497 (6)0.0435 (5)
C30.0021 (3)0.5128 (3)0.08041 (7)0.0580 (7)
H30.04570.56430.10100.070*
C40.0985 (3)0.5777 (3)0.05567 (8)0.0618 (7)
H40.12100.67330.05920.074*
C50.1654 (3)0.5023 (2)0.02586 (8)0.0518 (6)
H50.23350.54660.00920.062*
C60.1323 (2)0.3610 (2)0.02049 (7)0.0434 (5)
H60.17890.30980.00040.052*
C70.0300 (2)0.2947 (2)0.04485 (6)0.0373 (4)
C80.0158 (2)0.0388 (2)0.06027 (6)0.0399 (5)
C90.0015 (2)0.0533 (2)0.10436 (6)0.0416 (5)
C100.0895 (3)0.0641 (3)0.12279 (7)0.0555 (6)
H10A0.18790.06120.11140.067*
H10B0.04570.15470.11560.067*
C110.1027 (3)0.0572 (2)0.16758 (7)0.0489 (6)
C120.0147 (3)0.1404 (3)0.19132 (8)0.0590 (6)
H120.05240.20220.17940.071*
C130.0233 (3)0.1346 (3)0.23246 (8)0.0668 (7)
H130.03670.19220.24820.080*
C140.1208 (3)0.0436 (3)0.24963 (8)0.0639 (7)
C150.2101 (3)0.0408 (3)0.22704 (9)0.0733 (8)
H150.27660.10280.23910.088*
C160.2004 (3)0.0329 (3)0.18587 (8)0.0664 (7)
H160.26140.08990.17030.080*
N10.0078 (2)0.15261 (18)0.03612 (5)0.0405 (4)
H10.02900.13630.01150.049*
O10.0322 (2)0.08062 (16)0.04596 (4)0.0551 (4)
S10.17684 (7)0.29044 (7)0.104528 (18)0.0568 (2)
Cl10.13112 (12)0.03656 (12)0.30146 (2)0.1046 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0518 (13)0.0530 (13)0.0379 (11)0.0069 (11)0.0027 (10)0.0015 (10)
C20.0495 (13)0.0381 (12)0.0428 (11)0.0122 (10)0.0066 (9)0.0021 (9)
C30.0789 (18)0.0400 (13)0.0552 (14)0.0191 (13)0.0111 (13)0.0109 (11)
C40.0796 (19)0.0336 (12)0.0721 (17)0.0004 (12)0.0225 (15)0.0012 (12)
C50.0508 (14)0.0379 (12)0.0667 (15)0.0020 (11)0.0135 (12)0.0109 (11)
C60.0418 (11)0.0363 (12)0.0522 (12)0.0045 (9)0.0039 (10)0.0036 (9)
C70.0389 (11)0.0328 (10)0.0400 (10)0.0049 (9)0.0067 (8)0.0009 (8)
C80.0440 (12)0.0361 (12)0.0396 (10)0.0032 (9)0.0035 (9)0.0018 (9)
C90.0469 (12)0.0398 (12)0.0380 (10)0.0010 (10)0.0028 (9)0.0018 (9)
C100.0696 (16)0.0478 (13)0.0492 (13)0.0110 (12)0.0046 (12)0.0040 (11)
C110.0515 (14)0.0455 (13)0.0497 (12)0.0084 (11)0.0005 (10)0.0095 (10)
C120.0615 (16)0.0559 (15)0.0595 (14)0.0044 (13)0.0010 (12)0.0090 (12)
C130.0687 (18)0.0723 (18)0.0593 (15)0.0046 (15)0.0117 (14)0.0210 (14)
C140.0653 (17)0.0791 (18)0.0472 (13)0.0228 (15)0.0080 (12)0.0081 (13)
C150.0719 (19)0.078 (2)0.0698 (17)0.0061 (16)0.0219 (15)0.0040 (15)
C160.0631 (17)0.0714 (18)0.0645 (16)0.0115 (14)0.0025 (13)0.0179 (14)
N10.0527 (11)0.0347 (9)0.0342 (8)0.0024 (8)0.0011 (8)0.0025 (7)
O10.0836 (12)0.0365 (8)0.0453 (8)0.0120 (8)0.0058 (8)0.0030 (7)
S10.0541 (4)0.0654 (4)0.0509 (3)0.0224 (3)0.0093 (3)0.0030 (3)
Cl10.1122 (7)0.1522 (9)0.0494 (4)0.0371 (7)0.0121 (4)0.0051 (5)
Geometric parameters (Å, º) top
C1—C91.320 (3)C8—C91.488 (3)
C1—S11.758 (2)C9—C101.509 (3)
C1—H1A0.9300C10—C111.506 (3)
C2—C71.386 (3)C10—H10A0.9700
C2—C31.391 (3)C10—H10B0.9700
C2—S11.761 (2)C11—C161.370 (4)
C3—C41.374 (4)C11—C121.371 (3)
C3—H30.9300C12—C131.381 (4)
C4—C51.366 (4)C12—H120.9300
C4—H40.9300C13—C141.357 (4)
C5—C61.374 (3)C13—H130.9300
C5—H50.9300C14—C151.363 (4)
C6—C71.382 (3)C14—Cl11.739 (3)
C6—H60.9300C15—C161.383 (4)
C7—N11.411 (3)C15—H150.9300
C8—O11.231 (2)C16—H160.9300
C8—N11.344 (3)N1—H10.8600
C9—C1—S1125.10 (17)C11—C10—H10A108.6
C9—C1—H1A117.5C9—C10—H10A108.6
S1—C1—H1A117.5C11—C10—H10B108.6
C7—C2—C3118.8 (2)C9—C10—H10B108.6
C7—C2—S1120.49 (17)H10A—C10—H10B107.6
C3—C2—S1120.64 (18)C16—C11—C12118.0 (2)
C4—C3—C2120.6 (2)C16—C11—C10121.6 (2)
C4—C3—H3119.7C12—C11—C10120.5 (2)
C2—C3—H3119.7C11—C12—C13121.5 (3)
C5—C4—C3120.2 (2)C11—C12—H12119.2
C5—C4—H4119.9C13—C12—H12119.2
C3—C4—H4119.9C14—C13—C12119.0 (3)
C4—C5—C6120.1 (2)C14—C13—H13120.5
C4—C5—H5120.0C12—C13—H13120.5
C6—C5—H5120.0C13—C14—C15121.2 (3)
C5—C6—C7120.4 (2)C13—C14—Cl1118.8 (2)
C5—C6—H6119.8C15—C14—Cl1120.0 (2)
C7—C6—H6119.8C14—C15—C16118.9 (3)
C6—C7—C2119.92 (19)C14—C15—H15120.5
C6—C7—N1117.91 (18)C16—C15—H15120.5
C2—C7—N1122.02 (19)C11—C16—C15121.3 (3)
O1—C8—N1119.98 (18)C11—C16—H16119.3
O1—C8—C9118.70 (18)C15—C16—H16119.3
N1—C8—C9121.31 (18)C8—N1—C7130.05 (17)
C1—C9—C8123.0 (2)C8—N1—H1115.0
C1—C9—C10124.05 (19)C7—N1—H1115.0
C8—C9—C10112.71 (18)C1—S1—C299.08 (10)
C11—C10—C9114.76 (19)
C7—C2—C3—C41.7 (3)C9—C10—C11—C1679.7 (3)
S1—C2—C3—C4175.82 (19)C9—C10—C11—C1299.3 (3)
C2—C3—C4—C51.3 (4)C16—C11—C12—C130.1 (4)
C3—C4—C5—C60.0 (4)C10—C11—C12—C13179.1 (2)
C4—C5—C6—C70.7 (3)C11—C12—C13—C140.4 (4)
C5—C6—C7—C20.2 (3)C12—C13—C14—C150.4 (4)
C5—C6—C7—N1175.39 (19)C12—C13—C14—Cl1179.9 (2)
C3—C2—C7—C61.0 (3)C13—C14—C15—C160.0 (4)
S1—C2—C7—C6176.59 (15)Cl1—C14—C15—C16179.7 (2)
C3—C2—C7—N1176.41 (19)C12—C11—C16—C150.3 (4)
S1—C2—C7—N11.2 (3)C10—C11—C16—C15178.7 (2)
S1—C1—C9—C86.9 (3)C14—C15—C16—C110.3 (4)
S1—C1—C9—C10179.25 (19)O1—C8—N1—C7170.5 (2)
O1—C8—C9—C1135.4 (2)C9—C8—N1—C78.1 (3)
N1—C8—C9—C146.0 (3)C6—C7—N1—C8131.7 (2)
O1—C8—C9—C1039.0 (3)C2—C7—N1—C852.8 (3)
N1—C8—C9—C10139.5 (2)C9—C1—S1—C258.0 (2)
C1—C9—C10—C113.5 (3)C7—C2—S1—C160.21 (19)
C8—C9—C10—C11177.9 (2)C3—C2—S1—C1122.26 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.072.854 (2)151
Symmetry code: (i) x, y, z.

Experimental details

Crystal data
Chemical formulaC16H12ClNOS
Mr301.78
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)9.0486 (3), 9.4105 (3), 33.4876 (10)
V3)2851.53 (16)
Z8
Radiation typeMo Kα
µ (mm1)0.41
Crystal size (mm)0.23 × 0.21 × 0.15
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.910, 0.941
No. of measured, independent and
observed [I > 2σ(I)] reflections
14850, 3099, 2382
Rint0.029
(sin θ/λ)max1)0.640
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.118, 1.03
No. of reflections3099
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.45

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.072.854 (2)151
Symmetry code: (i) x, y, z.
 

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 citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science 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. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationMetys, J., Metysova, J. & Votava, Z. (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 citationSabari, V., Jagadeesan, G., Selvakumar, R., Bakthadoss, M. & Aravindhan, S. (2011). Acta Cryst. E67, o3061.  Web of Science CSD CrossRef IUCr Journals 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
First citationSridevi, D., Bhaskaran, S., Usha, G., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o243.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationTomascovic, L. L., Arneri, R. S., Brundic, A. H., Nagl, A., Mintas, M. & Sandtrom, J. (2000). Helv. Chim. Acta, 83, 479–493.  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