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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 o45-o46
https://doi.org/10.1107/S2056989014026723

Crystal structure of N′-[(E)-(4-chloro­phen­yl)(phen­yl)methyl­­idene]-4-methyl­benzene­sulfono­hydrazide

J. Balaji,a S. Prabu,a J. J. F. Xavierb and P. Srinivasana*

aDepartment of Physics, UCEP, Panruti 607 106, TamilNadu, India, and bDepartment of Chemistry, UCEP, Panruti 607 106, TamilNadu, India
*Correspondence e-mail: sril35@gmail.com

Edited by G. Smith, Queensland University of Technology, Australia (Received 16 October 2014; accepted 5 December 2014; online 1 January 2015)

The title compound, C20H17ClN2O2S, was obtained by a condensation reaction between 4-chloro­benzo­phenone and tosyl hydrazide. The plane of the methyl-substituted benzene ring forms dihedral angles of 20.12 (12) and 78.43 (13)° with those of the chlorine-substituted benzene ring and the benzene ring, respectively, with the last two rings forming a dihedral angle of 67.81 (13)°. The chlorine substituent was also found to be 0.868 (2):0.132 (2) disordered over these two rings. In the crystal, mol­ecules are linked through pairs of N—H⋯O hydrogen bonds, giving centrosymmetric cyclic dimers [graph set R22(8)], which are linked by weak C—H⋯O and C—H⋯Cl inter­actions into a chain structure which extends along the a-axis direction.

CCDC reference: 1037752

Similar articles

1. Related literature

Benzo­phenone and its derivatives have been investigated extensively for their biological activities such as anti-fungal and anti-inflammatory, see: Khanum et al. (2004[Khanum, S. A., Venu, T. D., Shashikanth, S. & Firdouse, A. (2004). Bioorg. Med. Chem. Lett. 12, 2093-2095.]). For similar structures, see: Ajani et al. (2010[Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214-221.]); Gerdemann et al. (2002[Gerdemann, C., Eicken, C. & Krebs, B. (2002). Acc. Chem. Res. 35, 183-191.]); Kutzke et al. (2000[Kutzke, H., Klapper, H., Hammond, R. B. & Roberts, K. J. (2000). Acta Cryst. B56, 486-496.]); Shen et al. (2012[Shen, X.-H., Zhu, L.-X., Shao, L.-J. & Zhu, Z.-F. (2012). Acta Cryst. E68, o297.]); Zhang (2011[Zhang, W.-G. (2011). Acta Cryst. E67, o233.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C20H17ClN2O2S

  • Mr = 384.87

  • Monoclinic, P 21 /c

  • a = 12.6808 (6) Å

  • b = 9.3857 (5) Å

  • c = 16.3974 (7) Å

  • β = 106.187 (2)°

  • V = 1874.22 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.33 mm−1

  • T = 293 K

  • 0.35 × 0.30 × 0.25 mm

2.2. Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.891, Tmax = 0.930

  • 21401 measured reflections

  • 3300 independent reflections

  • 2416 reflections with I > 2σ(I)

  • Rint = 0.032

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.105

  • S = 1.06

  • 3300 reflections

  • 253 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O2i 0.88 (2) 2.19 (2) 3.024 (3) 160 (2)
C10—H10⋯Cl1′ii 0.93 2.76 3.476 (7) 134
C16—H16⋯O1iii 0.93 2.54 3.339 (3) 145
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+2, -y+2, -z+1.

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: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); 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.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1037752

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989014026723/zs2319sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989014026723/zs2319Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989014026723/zs2319Isup3.cml

checkCIF report


Chemical context top

Currently the hydrazones have attracted considerable attention due to their biological activities and a number of crystal structures of these compounds have been reported (Ajani et al., 2010); Gerdemann et al., 2002; Kutzke et al., 2000); Zhang, 2011; Shen et al., 2012). Benzo­phenone and its derivatives have also been extensively investigated for their biological activities such as anti-fungal and anti-inflammatory (Khanum et al., 2004). In view of the importance of these analogs, the title compound, C20H17ClN2O2S, was synthesized in a Schiff base condensation reaction between 4-chloro­benzo­phenone and tosyl hydrazide and its structure is reported herein.

In this compound (Fig. 1) the benzene ring (C1–C6) forms dihedral angles of 20.12 (12) and 78.43 (13)° with the chlorine-substituted benzene ring (C8–C13) and the benzene ring (C14–C19), respectively. The molecule is twisted, with the dihedral angle between the two benzene rings (C8–C13 and C14–C19) of the parent moiety being 67.81 (13)°. In the crystal, molecules are linked through inter­molecular N1—H···O2i hydrogen-bond pairs (Table 1) giving centrosymmetric cyclic dimers [graph set R22(8)] which are linked by weak C—H···O and C—H···Cl inter­actions into a chain structure which extends along a (Fig. 2).

Synthesis and crystallization top

4-Chloro­benzo­phenone (0.15g, 1 mmol) and tosyl hydrazide (0.186g, 1 mmol) were dissolved in ethanol (50 ml). The reaction mixture was heated under reflux for 3 hr and cooled gradually to room temperature. Crystals suitable for X-ray diffraction analysis were obtained by slow room temperature evaporation of the solution containing the compound.

Refinement top

All H atoms were positioned geometrically and treated as riding on their parent atoms with C—H = 0.93 Å (aromatic) or 0.96 Å (methyl) and N1—H = 0.89±2 Å with Uiso(H) = 1.2 Ueq(N, Caromatic) or 1.5 Ueq(Cmethyl). The chlorine substituent was also found to be disordered over the C8–C13 (Cl1) and C14–C19 (Cl1') rings of the original benzo­phenone moiety [occupancy factors 0.868 (2):0.132 (2), respectively].

Related literature top

Benzophenone and its derivatives have been investigated extensively for their biological activities such as anti-fungal and anti-inflammatory, see: Khanum et al. (2004). For similar structures, see: Ajani et al. (2010); Gerdemann et al. (2002); Kutzke et al. (2000); Shen et al. (2012); Zhang (2011).

Structure description top

Currently the hydrazones have attracted considerable attention due to their biological activities and a number of crystal structures of these compounds have been reported (Ajani et al., 2010); Gerdemann et al., 2002; Kutzke et al., 2000); Zhang, 2011; Shen et al., 2012). Benzo­phenone and its derivatives have also been extensively investigated for their biological activities such as anti-fungal and anti-inflammatory (Khanum et al., 2004). In view of the importance of these analogs, the title compound, C20H17ClN2O2S, was synthesized in a Schiff base condensation reaction between 4-chloro­benzo­phenone and tosyl hydrazide and its structure is reported herein.

In this compound (Fig. 1) the benzene ring (C1–C6) forms dihedral angles of 20.12 (12) and 78.43 (13)° with the chlorine-substituted benzene ring (C8–C13) and the benzene ring (C14–C19), respectively. The molecule is twisted, with the dihedral angle between the two benzene rings (C8–C13 and C14–C19) of the parent moiety being 67.81 (13)°. In the crystal, molecules are linked through inter­molecular N1—H···O2i hydrogen-bond pairs (Table 1) giving centrosymmetric cyclic dimers [graph set R22(8)] which are linked by weak C—H···O and C—H···Cl inter­actions into a chain structure which extends along a (Fig. 2).

Benzophenone and its derivatives have been investigated extensively for their biological activities such as anti-fungal and anti-inflammatory, see: Khanum et al. (2004). For similar structures, see: Ajani et al. (2010); Gerdemann et al. (2002); Kutzke et al. (2000); Shen et al. (2012); Zhang (2011).

Synthesis and crystallization top

4-Chloro­benzo­phenone (0.15g, 1 mmol) and tosyl hydrazide (0.186g, 1 mmol) were dissolved in ethanol (50 ml). The reaction mixture was heated under reflux for 3 hr and cooled gradually to room temperature. Crystals suitable for X-ray diffraction analysis were obtained by slow room temperature evaporation of the solution containing the compound.

Refinement details top

All H atoms were positioned geometrically and treated as riding on their parent atoms with C—H = 0.93 Å (aromatic) or 0.96 Å (methyl) and N1—H = 0.89±2 Å with Uiso(H) = 1.2 Ueq(N, Caromatic) or 1.5 Ueq(Cmethyl). The chlorine substituent was also found to be disordered over the C8–C13 (Cl1) and C14–C19 (Cl1') rings of the original benzo­phenone moiety [occupancy factors 0.868 (2):0.132 (2), respectively].

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: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the atom labelling scheme. The displacement ellipsoids are drawn at the 30% probability level
[Figure 2] Fig. 2. A view of the crystal packing of the title compound. The various hydrogen bonds are indicated by dashed lines (see Table 1 for details).
N'-[(E)-(4-Chlorophenyl)(phenyl)methylidene]-4-methylbenzenesulfonohydrazide top
Crystal data top
C20H17ClN2O2SF(000) = 800
Mr = 384.87Dx = 1.364 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6873 reflections
a = 12.6808 (6) Åθ = 2.5–25.2°
b = 9.3857 (5) ŵ = 0.33 mm−1
c = 16.3974 (7) ÅT = 293 K
β = 106.187 (2)°Block, brown
V = 1874.22 (16) Å30.35 × 0.30 × 0.25 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3300 independent reflections
Radiation source: fine-focus sealed tube2416 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω and φ scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→15
Tmin = 0.891, Tmax = 0.930k = −11→11
21401 measured reflectionsl = −18→19
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)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0351P)2 + 1.1726P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
3300 reflectionsΔρmax = 0.35 e Å−3
253 parametersΔρmin = −0.33 e Å−3
4 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0025 (7)
Crystal data top
C20H17ClN2O2SV = 1874.22 (16) Å3
Mr = 384.87Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.6808 (6) ŵ = 0.33 mm−1
b = 9.3857 (5) ÅT = 293 K
c = 16.3974 (7) Å0.35 × 0.30 × 0.25 mm
β = 106.187 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3300 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2416 reflections with I > 2σ(I)
Tmin = 0.891, Tmax = 0.930Rint = 0.032
21401 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0394 restraints
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.35 e Å−3
3300 reflectionsΔρmin = −0.33 e Å−3
253 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*/UeqOcc. (<1)
C10.6473 (2)0.5896 (3)0.50383 (16)0.0567 (7)
H10.58300.60140.51980.068*
C20.6980 (3)0.4588 (3)0.51169 (18)0.0650 (8)
H20.66760.38250.53340.078*
C30.7928 (3)0.4383 (3)0.48812 (18)0.0632 (7)
C40.8369 (2)0.5531 (3)0.45737 (17)0.0612 (7)
H40.90130.54100.44160.073*
C50.7885 (2)0.6855 (3)0.44933 (16)0.0510 (6)
H50.82000.76210.42880.061*
C60.69263 (19)0.7028 (3)0.47211 (14)0.0445 (6)
C70.81124 (18)1.0259 (2)0.65813 (15)0.0430 (6)
C80.73683 (18)1.0797 (3)0.70683 (14)0.0429 (6)
C90.7223 (2)1.2238 (3)0.71776 (16)0.0511 (6)
H90.76121.28980.69530.061*
C100.6505 (2)1.2706 (3)0.76179 (17)0.0581 (7)
H100.64051.36750.76910.070*
C110.5943 (2)1.1708 (3)0.79449 (16)0.0587 (7)
C120.6081 (2)1.0282 (3)0.78491 (17)0.0605 (7)
H120.56920.96240.80770.073*
C130.6794 (2)0.9831 (3)0.74156 (15)0.0525 (6)
H130.68950.88590.73530.063*
C140.93096 (18)1.0480 (3)0.68959 (15)0.0453 (6)
C150.9995 (2)1.0041 (3)0.64206 (17)0.0541 (7)
H150.96960.96080.58970.065*
C161.1112 (2)1.0234 (3)0.6711 (2)0.0632 (8)
H161.15660.99270.63880.076*
C171.1549 (2)1.0880 (3)0.7477 (2)0.0699 (9)
H171.2283 (17)1.100 (4)0.769 (2)0.084*
C181.0896 (2)1.1329 (3)0.7961 (2)0.0723 (8)
H181.12031.17700.84810.087*
C190.9777 (2)1.1124 (3)0.76732 (17)0.0610 (7)
H190.93311.14210.80050.073*
C200.8462 (3)0.2933 (4)0.4951 (3)0.1014 (12)
H20A0.89290.28900.45800.152*
H20B0.79050.22130.47910.152*
H20C0.88930.27760.55260.152*
N10.66524 (16)0.9315 (2)0.55792 (13)0.0548 (6)
N20.77696 (15)0.9565 (2)0.58850 (13)0.0498 (5)
O10.67110 (15)0.9520 (2)0.40485 (12)0.0639 (5)
O20.51226 (13)0.8526 (2)0.44334 (11)0.0599 (5)
S10.62845 (5)0.86959 (7)0.46061 (4)0.0477 (2)
Cl10.50538 (8)1.22428 (12)0.85037 (6)0.0880 (4)0.868 (2)
Cl1'1.2814 (4)1.1131 (6)0.7865 (4)0.0616 (19)0.132 (2)
H1A0.6174 (19)0.988 (2)0.5711 (16)0.061 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0582 (16)0.0650 (18)0.0486 (15)−0.0090 (14)0.0175 (12)−0.0045 (13)
C20.078 (2)0.0537 (18)0.0595 (17)−0.0106 (15)0.0136 (15)0.0068 (14)
C30.073 (2)0.0506 (17)0.0568 (17)0.0071 (14)0.0038 (14)0.0010 (14)
C40.0578 (17)0.0611 (18)0.0649 (18)0.0115 (14)0.0173 (14)−0.0015 (14)
C50.0493 (15)0.0498 (15)0.0558 (16)0.0009 (12)0.0179 (12)0.0001 (12)
C60.0467 (14)0.0476 (14)0.0371 (13)−0.0008 (11)0.0081 (11)−0.0058 (11)
C70.0414 (13)0.0402 (13)0.0454 (14)0.0014 (10)0.0087 (11)−0.0039 (11)
C80.0381 (12)0.0476 (14)0.0408 (13)−0.0034 (10)0.0072 (10)−0.0069 (11)
C90.0473 (14)0.0517 (15)0.0577 (16)−0.0038 (12)0.0200 (12)−0.0072 (12)
C100.0584 (16)0.0554 (16)0.0617 (17)0.0062 (13)0.0191 (14)−0.0084 (14)
C110.0449 (15)0.085 (2)0.0483 (15)0.0102 (14)0.0167 (12)0.0013 (15)
C120.0563 (16)0.075 (2)0.0517 (16)−0.0085 (15)0.0174 (13)0.0071 (14)
C130.0557 (15)0.0526 (15)0.0478 (15)−0.0043 (12)0.0122 (12)−0.0031 (12)
C140.0399 (13)0.0422 (13)0.0510 (15)0.0005 (10)0.0081 (11)0.0014 (11)
C150.0471 (14)0.0533 (16)0.0627 (17)0.0036 (12)0.0165 (13)0.0001 (13)
C160.0457 (15)0.0585 (17)0.088 (2)0.0035 (13)0.0225 (15)0.0049 (16)
C170.0399 (15)0.0563 (18)0.104 (3)−0.0040 (14)0.0041 (17)0.0068 (17)
C180.0513 (17)0.073 (2)0.078 (2)−0.0055 (15)−0.0058 (15)−0.0135 (17)
C190.0481 (15)0.0690 (18)0.0612 (17)−0.0013 (13)0.0076 (13)−0.0123 (15)
C200.122 (3)0.059 (2)0.114 (3)0.022 (2)0.018 (2)0.010 (2)
N10.0370 (12)0.0694 (15)0.0555 (13)0.0035 (10)0.0089 (10)−0.0248 (11)
N20.0361 (11)0.0558 (13)0.0544 (13)0.0033 (9)0.0071 (9)−0.0145 (10)
O10.0688 (12)0.0634 (12)0.0642 (12)0.0126 (10)0.0262 (10)0.0144 (10)
O20.0382 (9)0.0772 (13)0.0585 (11)0.0056 (9)0.0038 (8)−0.0159 (10)
S10.0428 (3)0.0552 (4)0.0435 (4)0.0046 (3)0.0095 (3)−0.0070 (3)
Cl10.0827 (7)0.1092 (8)0.0920 (7)0.0402 (6)0.0573 (6)0.0216 (6)
Cl1'0.044 (3)0.065 (4)0.067 (4)−0.011 (3)0.001 (2)−0.003 (3)
Geometric parameters (Å, º) top
C1—C21.375 (4)C12—C131.364 (4)
C1—C61.378 (3)C12—H120.9300
C1—H10.9300C13—H130.9300
C2—C31.374 (4)C14—C151.382 (3)
C2—H20.9300C14—C191.385 (3)
C3—C41.373 (4)C15—C161.374 (4)
C3—C201.510 (4)C15—H150.9300
C4—C51.376 (4)C16—C171.366 (4)
C4—H40.9300C16—H160.9300
C5—C61.377 (3)C17—C181.363 (4)
C5—H50.9300C17—Cl1'1.570 (5)
C6—S11.750 (2)C17—H170.905 (19)
C7—N21.281 (3)C18—C191.378 (4)
C7—C141.476 (3)C18—H180.9300
C7—C81.484 (3)C19—H190.9300
C8—C131.382 (3)C20—H20A0.9600
C8—C91.383 (3)C20—H20B0.9600
C9—C101.382 (3)C20—H20C0.9600
C9—H90.9300N1—N21.385 (3)
C10—C111.374 (4)N1—S11.639 (2)
C10—H100.9300N1—H1A0.877 (17)
C11—C121.365 (4)O1—S11.4150 (18)
C11—Cl11.714 (3)O2—S11.4296 (17)
C2—C1—C6119.4 (3)C8—C13—H13119.6
C2—C1—H1120.3C15—C14—C19118.3 (2)
C6—C1—H1120.3C15—C14—C7120.5 (2)
C3—C2—C1121.4 (3)C19—C14—C7121.2 (2)
C3—C2—H2119.3C16—C15—C14120.9 (3)
C1—C2—H2119.3C16—C15—H15119.5
C4—C3—C2118.1 (3)C14—C15—H15119.5
C4—C3—C20120.9 (3)C17—C16—C15119.5 (3)
C2—C3—C20120.9 (3)C17—C16—H16120.3
C3—C4—C5121.8 (3)C15—C16—H16120.3
C3—C4—H4119.1C18—C17—C16121.1 (3)
C5—C4—H4119.1C18—C17—Cl1'115.9 (3)
C4—C5—C6119.0 (2)C16—C17—Cl1'123.1 (3)
C4—C5—H5120.5C18—C17—H17118 (3)
C6—C5—H5120.5C16—C17—H17121 (2)
C5—C6—C1120.2 (2)C17—C18—C19119.5 (3)
C5—C6—S1119.72 (19)C17—C18—H18120.3
C1—C6—S1120.04 (19)C19—C18—H18120.3
N2—C7—C14116.3 (2)C18—C19—C14120.8 (3)
N2—C7—C8122.9 (2)C18—C19—H19119.6
C14—C7—C8120.7 (2)C14—C19—H19119.6
C13—C8—C9118.9 (2)C3—C20—H20A109.5
C13—C8—C7119.1 (2)C3—C20—H20B109.5
C9—C8—C7122.0 (2)H20A—C20—H20B109.5
C10—C9—C8120.6 (2)C3—C20—H20C109.5
C10—C9—H9119.7H20A—C20—H20C109.5
C8—C9—H9119.7H20B—C20—H20C109.5
C11—C10—C9118.4 (3)N2—N1—S1113.42 (16)
C11—C10—H10120.8N2—N1—H1A121.1 (18)
C9—C10—H10120.8S1—N1—H1A115.2 (17)
C12—C11—C10121.8 (2)C7—N2—N1117.89 (19)
C12—C11—Cl1118.3 (2)O1—S1—O2119.43 (12)
C10—C11—Cl1119.9 (2)O1—S1—N1112.27 (12)
C13—C12—C11119.3 (3)O2—S1—N1103.31 (11)
C13—C12—H12120.4O1—S1—C6107.96 (11)
C11—C12—H12120.4O2—S1—C6110.15 (12)
C12—C13—C8120.9 (3)N1—S1—C6102.39 (11)
C12—C13—H13119.6
C6—C1—C2—C3−0.4 (4)C8—C7—C14—C15−176.8 (2)
C1—C2—C3—C40.9 (4)N2—C7—C14—C19−175.2 (2)
C1—C2—C3—C20−178.5 (3)C8—C7—C14—C193.6 (4)
C2—C3—C4—C5−0.5 (4)C19—C14—C15—C160.1 (4)
C20—C3—C4—C5179.0 (3)C7—C14—C15—C16−179.6 (2)
C3—C4—C5—C6−0.5 (4)C14—C15—C16—C17−0.5 (4)
C4—C5—C6—C11.1 (4)C15—C16—C17—C180.4 (5)
C4—C5—C6—S1−178.9 (2)C15—C16—C17—Cl1'179.3 (3)
C2—C1—C6—C5−0.7 (4)C16—C17—C18—C190.2 (5)
C2—C1—C6—S1179.3 (2)Cl1'—C17—C18—C19−178.8 (3)
N2—C7—C8—C1364.3 (3)C17—C18—C19—C14−0.6 (5)
C14—C7—C8—C13−114.3 (3)C15—C14—C19—C180.5 (4)
N2—C7—C8—C9−115.0 (3)C7—C14—C19—C18−179.8 (3)
C14—C7—C8—C966.4 (3)C14—C7—N2—N1178.9 (2)
C13—C8—C9—C10−0.8 (4)C8—C7—N2—N10.2 (4)
C7—C8—C9—C10178.5 (2)S1—N1—N2—C7168.96 (19)
C8—C9—C10—C110.1 (4)N2—N1—S1—O1−50.0 (2)
C9—C10—C11—C120.4 (4)N2—N1—S1—O2−179.99 (18)
C9—C10—C11—Cl1179.4 (2)N2—N1—S1—C665.5 (2)
C10—C11—C12—C13−0.1 (4)C5—C6—S1—O117.3 (2)
Cl1—C11—C12—C13−179.2 (2)C1—C6—S1—O1−162.68 (19)
C11—C12—C13—C8−0.6 (4)C5—C6—S1—O2149.31 (19)
C9—C8—C13—C121.0 (4)C1—C6—S1—O2−30.7 (2)
C7—C8—C13—C12−178.3 (2)C5—C6—S1—N1−101.3 (2)
N2—C7—C14—C154.5 (3)C1—C6—S1—N178.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.88 (2)2.19 (2)3.024 (3)160 (2)
C1—H1···Cl1ii0.932.913.694 (3)143
C10—H10···Cl1′iii0.932.763.476 (7)134
C16—H16···O1iv0.932.543.339 (3)145
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+2, y+1/2, −z+3/2; (iv) −x+2, −y+2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.877 (17)2.186 (19)3.024 (3)160 (2)
C10—H10···Cl1'ii0.932.763.476 (7)134
C16—H16···O1iii0.932.543.339 (3)145
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, y+1/2, −z+3/2; (iii) −x+2, −y+2, −z+1.
 

Acknowledgements

JB thanks the CTDT, Anna University, for funding the project (AU/ROT/BIT/R&D/YFP/PAN/PHY/2013–14/001). The authors thank the SAIF, IITM, Madras, for helping with the XRD studies.

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ISSN: 2056-9890
Volume 71| Part 1| January 2015| Pages o45-o46
https://doi.org/10.1107/S2056989014026723
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