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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 66| Part 8| August 2010| Page o1899
https://doi.org/10.1107/S1600536810025389

N′-[Bis(benzyl­sulfan­yl)methyl­­idene]-4-meth­­oxy­benzohydrazide

Jerry P. Jasinski,a* Ray J. Butcher,b S. K. Kushawaha,c M. K. Bhartyc and N. K. Singhc

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and cDepartment of Chemistry, Banaras Hindu University, Varanasi 221 005, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 27 June 2010; accepted 28 June 2010; online 3 July 2010)

In the title compound, C23H22N2O2S2, the dihedral angles between the 4-meth­oxy-substituted phenyl ring and the other two phenyl rings are 84.4 (4) and 77.7 (1)°, respectively, while the dihedral angle between the two phenyl rings is 57.5 (2)°. The amino group is not involved in an N—H hydrogen bond. The crystal packing is established by inter­molecular C—H⋯O packing inter­actions involving a relatively rare weak three-center hydrogen bond between the keto O atom and H atoms of the two nearby phenyl rings, which link the mol­ecules into chains running along the a axis. Additional weak inter­molecular hydrogen-bond inter­actions between the 4-meth­oxy O atom and one of the phenyl rings and provide added stability to the crystal packing.

Related literature

For radiopharmaceutical applications of dithio­carbazate derivatives, see: Boschi et al. (2003[Boschi, A., Bolzati, C., Uccelli, L. & Duatti, A. (2003). Nucl. Med. Biol. 30, 381-387.]). For dithio­carbazate derivatives as anti­cancer and anti­microbial drugs, see: Bharti et al. (2000[Bharti, N., Maurya, M. R., Naqvi, F., Bhattcharya, A., Bhattacharya, S. & Azam, A. (2000). Eur. J. Med. Chem. 35, 481-486.]). For a related structure, see: Singh et al. (2007[Singh, N. K., Singh, M. & Butcher, R. J. (2007). Acta Cryst. E63, o4405.]).

[Scheme 1]

Experimental

Crystal data

  • C23H22N2O2S2

  • Mr = 422.55

  • Triclinic, [P \overline 1]

  • a = 9.838 (2) Å

  • b = 9.845 (2) Å

  • c = 11.307 (2) Å

  • α = 70.25 (3)°

  • β = 90.00 (3)°

  • γ = 89.37 (3)°

  • V = 1030.6 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 100 K

  • 0.30 × 0.26 × 0.22 mm
Data collection

  • Bruker APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.921, Tmax = 0.941

  • 12424 measured reflections

  • 6210 independent reflections

  • 5954 reflections with I > 2σ(I)

  • Rint = 0.015
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.06

  • 6210 reflections

  • 263 parameters

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C6A—H6AA⋯O1i 0.95 2.41 3.2516 (17) 147
C1B—H1BA⋯O1ii 0.99 2.35 3.2872 (16) 157
C3B—H3BA⋯O1iii 0.95 2.67 3.5351 (18) 152
C6B—H6BA⋯O2iv 0.95 2.47 3.4173 (17) 174
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) x-1, y, z; (iv) -x+1, -y+2, -z-1.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA, 2006.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA, 2006.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810025389/bt5283sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025389/bt5283Isup2.hkl

checkCIF report


Comment top

Dithiocarbazate derivatives have been widely studied in radiopharmaceutical applications (Boschi et al., 2003) and have potential biological activity as anticancer and antimicrobial drugs (Bharti et al., 2000). This functional group is of particular interest and can coordinate to metals to give structures with different geometries and properties. As a part of our ongoing research on the dithio derivatives of acid hydrazides, we report here the crystal structure of the title compound, C23H22N2O2S2, a new 4-methoxy benzoic acid bis benzyl sulfanyl methylene hydrazide with a relatively rare three-center donor hydrogen bond.

The sum of the angles around C1 (120.00 (8)°) and the S1A/C1/S1B bond angle of 117.52 (7)° indicated nearly planar sp2 hybridized behavior (Fig. 1). The molecule can be divided into three distinct fragments with regard to their spatial orientation viz keto-amide, 4-methoxy benzene and bis benzyl sulfanyl methylene groups. Regarding the keto-amide group, all three rings including the 4-methoxy benzene, and two separate benzyl rings [A & B] have their mean planes twisted by 25,7(7)°, [B] 69.1 (6)° and [A] 76.5 (8)°, respectively. The dihedral angle between the 4-methoxy benzene group and two nearby benzyl groups is [B] 84.4 (4)° and [A] 77.7 (0)°, respectively. The mean plane between the two separate benzyl groups [A & B] is 57.5 (2)°. The torsion angles around the keto-amide linkage provides geometric support to these twist angles (C1/N1/N2/C2 = 154.32 (10)°; O1/C2/C3/C4 = 151.22 (11)°; N2/N1/C1/S1A = -173.64 (7)°; N/2/N/1/C1/S1B = 6.23 (13)°). The mean planes of the two sulfanyl groups are twisted nearly perpendicular to the dihedral planes of their adjacent benzyl rings with angles of [A] 70.6 (7)° and [B] 77.6 (4)° separating their groups to avoid steric hindrance. The N1 atom in the amide linkage possesses distorted tetrahedral geometry (C1/N1/N2 = 112.66 (10)°) while the N2 atom lies in a more planar fashion (N1/N2/C2/O1 = -1.25 (17)°). The C1—N1 and C2—N2 bond lengths (1.29253 (14)Å and 1.3574 (14) Å) lie between typical C—N and C═N values owing to the extensive delocalization of π electron density over the C2/N2/N1/C1 linkage.

A relatively rare weak three-center hydrogen bond configuration and additional weak C–H···O donor hydrogen bonds can be seen linking the molecules into chains along the (011) plane (Fig. 2). Additional hydrogen bonds between the 4-methoxy oxygen atom (O2) and one of the benzyl groups (C6B–H6BA···O2) help to stabilize crystal packing.

Related literature top

For radiopharmaceutical applications of dithiocarbazate derivatives, see: Boschi et al. (2003). For dithiocarbazate derivatives as anticancer and antimicrobial drugs, see: Bharti et al. (2000). For a related structure, see: Singh et al. (2007).

Experimental top

The potassium salt of N'-(4-methoxy benzoyl) hydrazine carbodithioate was prepared by adding carbon disulfide (0.04 mol, 2.4 ml) to a solution of 4-methoxy benzoic acid hydrazide(0.02 mol, 3.32 g) and potassium hydroxide (0.02 mol, 1.12 g) in methanol (30 ml) then stirring the reaction mixture for 2 h. The solid separated was filtered off, washed with 10% (v/v) mixture of ethanol-ether and dried in vacuo. Yield 1.54 g, 55%, m.p. 518 K. The title compound was prepared by drop wise addition of benzyl chloride (0.02 mol, 2.53 g) to a suspension of potassium salt of N'-(4-methoxy benzoyl)hydrazine carbodithioate (0.01 mol, 2.80 g) in methanol (20 ml) and stirring the reaction mixture for a period of 5–6 h. The reaction mixture was filtered and the solution was evaporated almost to dryness. The solid was washed several times with carbon tetrachloride and then with chloroform and recrystallized from methanol. Transparent white shining crystals of (I) (m.p. 475 K), suitable for X-ray analysis were obtained by slow evaporation of the methanol solution over a period of 9–10 days (yield 2.53 g, 60%): Anal Calcd (%): C, 65.31; H, 5.20; N, 6.62; S, 15.17; Found(%) for C23H22N2O2S2 (422.55): C, 65.52; H, 5.15; N, 6.75; S, 15.30.

Refinement top

All of the H atoms were placed in their calculated positions and then refined using the riding model with C–H = 0.95–0.99 Å, N–H = 0.88\|A%, with Uiso(H) = 1.18–1.49Ueq(C) and Uiso(H) = 1.19Ueq(N).

Structure description top

Dithiocarbazate derivatives have been widely studied in radiopharmaceutical applications (Boschi et al., 2003) and have potential biological activity as anticancer and antimicrobial drugs (Bharti et al., 2000). This functional group is of particular interest and can coordinate to metals to give structures with different geometries and properties. As a part of our ongoing research on the dithio derivatives of acid hydrazides, we report here the crystal structure of the title compound, C23H22N2O2S2, a new 4-methoxy benzoic acid bis benzyl sulfanyl methylene hydrazide with a relatively rare three-center donor hydrogen bond.

The sum of the angles around C1 (120.00 (8)°) and the S1A/C1/S1B bond angle of 117.52 (7)° indicated nearly planar sp2 hybridized behavior (Fig. 1). The molecule can be divided into three distinct fragments with regard to their spatial orientation viz keto-amide, 4-methoxy benzene and bis benzyl sulfanyl methylene groups. Regarding the keto-amide group, all three rings including the 4-methoxy benzene, and two separate benzyl rings [A & B] have their mean planes twisted by 25,7(7)°, [B] 69.1 (6)° and [A] 76.5 (8)°, respectively. The dihedral angle between the 4-methoxy benzene group and two nearby benzyl groups is [B] 84.4 (4)° and [A] 77.7 (0)°, respectively. The mean plane between the two separate benzyl groups [A & B] is 57.5 (2)°. The torsion angles around the keto-amide linkage provides geometric support to these twist angles (C1/N1/N2/C2 = 154.32 (10)°; O1/C2/C3/C4 = 151.22 (11)°; N2/N1/C1/S1A = -173.64 (7)°; N/2/N/1/C1/S1B = 6.23 (13)°). The mean planes of the two sulfanyl groups are twisted nearly perpendicular to the dihedral planes of their adjacent benzyl rings with angles of [A] 70.6 (7)° and [B] 77.6 (4)° separating their groups to avoid steric hindrance. The N1 atom in the amide linkage possesses distorted tetrahedral geometry (C1/N1/N2 = 112.66 (10)°) while the N2 atom lies in a more planar fashion (N1/N2/C2/O1 = -1.25 (17)°). The C1—N1 and C2—N2 bond lengths (1.29253 (14)Å and 1.3574 (14) Å) lie between typical C—N and C═N values owing to the extensive delocalization of π electron density over the C2/N2/N1/C1 linkage.

A relatively rare weak three-center hydrogen bond configuration and additional weak C–H···O donor hydrogen bonds can be seen linking the molecules into chains along the (011) plane (Fig. 2). Additional hydrogen bonds between the 4-methoxy oxygen atom (O2) and one of the benzyl groups (C6B–H6BA···O2) help to stabilize crystal packing.

For radiopharmaceutical applications of dithiocarbazate derivatives, see: Boschi et al. (2003). For dithiocarbazate derivatives as anticancer and antimicrobial drugs, see: Bharti et al. (2000). For a related structure, see: Singh et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of C23H22N2O2S2, showing the atom labeling scheme and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of C23H22N2O2S2,, viewed down the b axis. Dashed lines indicate weak intermolecular C—H···O hydrogen bonding interactions.
N'-[Bis(benzylsulfanyl)methylidene]-4-methoxybenzohydrazide top
Crystal data top
C23H22N2O2S2Z = 2
Mr = 422.55F(000) = 444
Triclinic, P1Dx = 1.362 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.838 (2) ÅCell parameters from 5412 reflections
b = 9.845 (2) Åθ = 2.4–30.5°
c = 11.307 (2) ŵ = 0.28 mm−1
α = 70.25 (3)°T = 100 K
β = 90.00 (3)°Chunk, colorless
γ = 89.37 (3)°0.30 × 0.26 × 0.22 mm
V = 1030.6 (4) Å3
Data collection top
Bruker APEX CCD area-detector
diffractometer		6210 independent reflections
Radiation source: fine-focus sealed tube5954 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
Detector resolution: 8.33 pixels mm-1θmax = 30.5°, θmin = 1.9°
φ and ω scansh = −14→14
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −14→14
Tmin = 0.921, Tmax = 0.941l = −16→16
12424 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0512P)2 + 0.4754P]
where P = (Fo2 + 2Fc2)/3
6210 reflections(Δ/σ)max = 0.001
263 parametersΔρmax = 0.56 e Å−3
0 restraintsΔρmin = −0.35 e Å−3
Crystal data top
C23H22N2O2S2γ = 89.37 (3)°
Mr = 422.55V = 1030.6 (4) Å3
Triclinic, P1Z = 2
a = 9.838 (2) ÅMo Kα radiation
b = 9.845 (2) ŵ = 0.28 mm−1
c = 11.307 (2) ÅT = 100 K
α = 70.25 (3)°0.30 × 0.26 × 0.22 mm
β = 90.00 (3)°
Data collection top
Bruker APEX CCD area-detector
diffractometer		6210 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5954 reflections with I > 2σ(I)
Tmin = 0.921, Tmax = 0.941Rint = 0.015
12424 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.06Δρmax = 0.56 e Å−3
6210 reflectionsΔρmin = −0.35 e Å−3
263 parameters
Special details top

Experimental. Spectroscopic analysis: IR(KBr, ν cm-1): 3285, (–NH); 1664, (C=O); 1604, (Thioamide I[β(NH + ν(CN)]; 1309, (Thioamide II [ν(CN) + β(NH)]; 760, (Thioamide IV, ν(C—S); 1068 (N—N). 1H NMR (CDCl3, δ, p.p.m.): 1.80, (s, 3H, OCH3); 4.25(d, 4H, –CH2); 9.40, (s, 1H, NH); 6.90, (m,5H, phenyl ring); 7.35 – 7.46, (m,10H, –CH2Ph); 13C NMR (CDCl3, δ, p.p.m.): 193.14, (C—S); 162.40, (C=O); 136.66, (C4,8); 115.92, (C5,7); 125.03, (C6); 128.37, (C3); 127.84, (C2A); 112.34, (C3A,7 A); 129.76, (C4A,6 A); 127.78, (C5A); 55.31,(CH2); 36.66, (CH3).

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 on F2 against ALL reflections. Weighted R-factors wR and all goodnesses 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
S1A0.34589 (3)0.41786 (3)0.19374 (2)0.01665 (7)
S1B0.33079 (3)0.67558 (3)−0.04284 (2)0.01674 (7)
O10.79463 (8)0.72953 (9)0.08230 (8)0.01885 (16)
O20.78658 (9)1.34644 (9)−0.34225 (8)0.01967 (16)
N10.53203 (9)0.62306 (10)0.12649 (9)0.01678 (17)
N20.56651 (9)0.75955 (10)0.04495 (9)0.01679 (17)
H2A0.50150.81880.00370.020*
C10.41847 (11)0.57822 (11)0.09652 (10)0.01510 (18)
C20.69749 (11)0.80369 (11)0.02737 (10)0.01495 (18)
C30.71432 (10)0.95034 (11)−0.06794 (10)0.01506 (18)
C40.62403 (11)1.01134 (12)−0.16830 (11)0.0182 (2)
H4A0.54400.9612−0.17490.022*
C50.65070 (11)1.14405 (12)−0.25784 (11)0.0190 (2)
H5A0.58861.1852−0.32520.023*
C60.76938 (11)1.21779 (11)−0.24914 (10)0.01585 (19)
C70.86039 (11)1.15852 (12)−0.14981 (10)0.01734 (19)
H7A0.94101.2080−0.14360.021*
C80.83092 (11)1.02579 (12)−0.06019 (10)0.01714 (19)
H8A0.89200.98550.00810.021*
C90.90880 (12)1.42350 (13)−0.33998 (11)0.0214 (2)
H9A0.90941.5135−0.41200.032*
H9B0.98781.3639−0.34450.032*
H9C0.91281.4458−0.26190.032*
C1A0.46244 (12)0.37100 (16)0.32723 (11)0.0269 (3)
H1AA0.54180.31750.31060.032*
H1AB0.49570.46020.33880.032*
C2A0.39201 (11)0.27942 (12)0.44481 (10)0.0182 (2)
C3A0.37413 (13)0.13247 (13)0.47003 (13)0.0242 (2)
H3AA0.40410.08870.41140.029*
C4A0.31194 (15)0.04925 (15)0.58191 (14)0.0337 (3)
H4AA0.2996−0.05120.59920.040*
C5A0.26837 (14)0.11268 (19)0.66751 (13)0.0371 (4)
H5AA0.22670.05570.74370.045*
C6A0.28544 (14)0.25882 (19)0.64225 (12)0.0331 (3)
H6AA0.25540.30250.70090.040*
C7A0.34638 (13)0.34147 (14)0.53129 (12)0.0244 (2)
H7AA0.35710.44210.51410.029*
C1B0.17073 (11)0.58242 (12)−0.03828 (10)0.01767 (19)
H1BA0.18680.4789−0.02530.021*
H1BB0.11170.59090.02980.021*
C2B0.10777 (11)0.65860 (11)−0.16520 (10)0.01608 (19)
C3B0.00363 (12)0.76019 (13)−0.17959 (12)0.0214 (2)
H3BA−0.03150.7787−0.10820.026*
C4B−0.04888 (13)0.83455 (14)−0.29857 (13)0.0277 (3)
H4BA−0.12060.9029−0.30810.033*
C5B0.00326 (14)0.80896 (14)−0.40303 (12)0.0287 (3)
H5BA−0.03240.8602−0.48420.034*
C6B0.10777 (13)0.70825 (14)−0.38928 (11)0.0249 (2)
H6BA0.14400.6915−0.46110.030*
C7B0.15918 (12)0.63218 (12)−0.27049 (11)0.0194 (2)
H7BA0.22930.5622−0.26100.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.01578 (12)0.01722 (12)0.01415 (12)−0.00345 (9)−0.00047 (9)−0.00155 (9)
S1B0.01535 (12)0.01657 (12)0.01539 (12)−0.00216 (9)−0.00130 (9)−0.00152 (9)
O10.0167 (4)0.0186 (4)0.0182 (4)0.0004 (3)−0.0014 (3)−0.0023 (3)
O20.0205 (4)0.0164 (4)0.0183 (4)−0.0038 (3)−0.0003 (3)−0.0007 (3)
N10.0166 (4)0.0150 (4)0.0168 (4)−0.0024 (3)0.0016 (3)−0.0026 (3)
N20.0145 (4)0.0142 (4)0.0188 (4)−0.0014 (3)−0.0007 (3)−0.0018 (3)
C10.0156 (4)0.0151 (4)0.0136 (4)0.0003 (3)0.0003 (3)−0.0036 (3)
C20.0156 (4)0.0156 (4)0.0139 (4)−0.0018 (3)0.0008 (3)−0.0052 (4)
C30.0143 (4)0.0146 (4)0.0155 (4)−0.0004 (3)0.0000 (3)−0.0040 (4)
C40.0164 (5)0.0185 (5)0.0182 (5)−0.0026 (4)−0.0030 (4)−0.0042 (4)
C50.0180 (5)0.0193 (5)0.0172 (5)−0.0007 (4)−0.0039 (4)−0.0028 (4)
C60.0168 (4)0.0145 (4)0.0153 (4)−0.0002 (3)0.0014 (3)−0.0037 (4)
C70.0152 (4)0.0171 (5)0.0184 (5)−0.0022 (4)−0.0005 (4)−0.0041 (4)
C80.0145 (4)0.0177 (5)0.0174 (5)−0.0004 (4)−0.0021 (4)−0.0036 (4)
C90.0204 (5)0.0198 (5)0.0215 (5)−0.0054 (4)0.0032 (4)−0.0034 (4)
C1A0.0185 (5)0.0365 (7)0.0165 (5)−0.0083 (5)−0.0030 (4)0.0032 (5)
C2A0.0152 (4)0.0204 (5)0.0146 (4)−0.0019 (4)−0.0026 (4)−0.0003 (4)
C3A0.0221 (5)0.0212 (5)0.0283 (6)0.0004 (4)−0.0042 (4)−0.0071 (5)
C4A0.0268 (6)0.0224 (6)0.0393 (8)−0.0069 (5)−0.0087 (5)0.0061 (5)
C5A0.0208 (6)0.0525 (9)0.0213 (6)−0.0036 (6)−0.0004 (5)0.0096 (6)
C6A0.0250 (6)0.0549 (9)0.0175 (5)0.0098 (6)−0.0031 (4)−0.0101 (6)
C7A0.0251 (6)0.0260 (6)0.0212 (5)0.0043 (4)−0.0073 (4)−0.0071 (4)
C1B0.0163 (4)0.0185 (5)0.0159 (4)−0.0033 (4)−0.0008 (4)−0.0027 (4)
C2B0.0145 (4)0.0161 (4)0.0158 (4)−0.0029 (3)−0.0009 (3)−0.0030 (4)
C3B0.0173 (5)0.0220 (5)0.0237 (5)0.0004 (4)−0.0003 (4)−0.0064 (4)
C4B0.0219 (5)0.0234 (6)0.0324 (6)0.0024 (4)−0.0083 (5)−0.0026 (5)
C5B0.0304 (6)0.0262 (6)0.0224 (6)−0.0083 (5)−0.0101 (5)0.0014 (5)
C6B0.0291 (6)0.0287 (6)0.0165 (5)−0.0110 (5)0.0006 (4)−0.0068 (4)
C7B0.0181 (5)0.0212 (5)0.0193 (5)−0.0037 (4)0.0013 (4)−0.0075 (4)
Geometric parameters (Å, º) top
S1A—C11.7500 (13)C1A—H1AB0.9900
S1A—C1A1.8231 (14)C2A—C7A1.3887 (17)
S1B—C11.7626 (13)C2A—C3A1.3899 (17)
S1B—C1B1.8230 (12)C3A—C4A1.399 (2)
O1—C21.2289 (14)C3A—H3AA0.9500
O2—C61.3582 (14)C4A—C5A1.383 (2)
O2—C91.4336 (14)C4A—H4AA0.9500
N1—C11.2923 (14)C5A—C6A1.381 (2)
N1—N21.3941 (13)C5A—H5AA0.9500
N2—C21.3574 (14)C6A—C7A1.384 (2)
N2—H2A0.8800C6A—H6AA0.9500
C2—C31.4923 (15)C7A—H7AA0.9500
C3—C81.3920 (15)C1B—C2B1.5060 (16)
C3—C41.4019 (16)C1B—H1BA0.9900
C4—C51.3836 (16)C1B—H1BB0.9900
C4—H4A0.9500C2B—C3B1.3942 (16)
C5—C61.4025 (16)C2B—C7B1.3954 (16)
C5—H5A0.9500C3B—C4B1.3925 (18)
C6—C71.3961 (16)C3B—H3BA0.9500
C7—C81.3899 (16)C4B—C5B1.386 (2)
C7—H7A0.9500C4B—H4BA0.9500
C8—H8A0.9500C5B—C6B1.392 (2)
C9—H9A0.9800C5B—H5BA0.9500
C9—H9B0.9800C6B—C7B1.3902 (17)
C9—H9C0.9800C6B—H6BA0.9500
C1A—C2A1.5047 (17)C7B—H7BA0.9500
C1A—H1AA0.9900
C1—S1A—C1A100.40 (6)C7A—C2A—C3A119.11 (11)
C1—S1B—C1B106.17 (6)C7A—C2A—C1A119.74 (11)
C6—O2—C9117.42 (9)C3A—C2A—C1A121.13 (12)
C1—N1—N2112.66 (10)C2A—C3A—C4A119.85 (13)
C2—N2—N1121.87 (9)C2A—C3A—H3AA120.1
C2—N2—H2A119.1C4A—C3A—H3AA120.1
N1—N2—H2A119.1C5A—C4A—C3A120.22 (13)
N1—C1—S1A120.92 (9)C5A—C4A—H4AA119.9
N1—C1—S1B121.56 (9)C3A—C4A—H4AA119.9
S1A—C1—S1B117.52 (7)C6A—C5A—C4A119.99 (13)
O1—C2—N2123.68 (10)C6A—C5A—H5AA120.0
O1—C2—C3122.39 (10)C4A—C5A—H5AA120.0
N2—C2—C3113.91 (10)C5A—C6A—C7A119.87 (14)
C8—C3—C4118.76 (10)C5A—C6A—H6AA120.1
C8—C3—C2117.52 (10)C7A—C6A—H6AA120.1
C4—C3—C2123.59 (10)C6A—C7A—C2A120.96 (13)
C5—C4—C3120.45 (10)C6A—C7A—H7AA119.5
C5—C4—H4A119.8C2A—C7A—H7AA119.5
C3—C4—H4A119.8C2B—C1B—S1B104.01 (8)
C4—C5—C6119.97 (10)C2B—C1B—H1BA111.0
C4—C5—H5A120.0S1B—C1B—H1BA111.0
C6—C5—H5A120.0C2B—C1B—H1BB111.0
O2—C6—C7124.37 (10)S1B—C1B—H1BB111.0
O2—C6—C5115.33 (10)H1BA—C1B—H1BB109.0
C7—C6—C5120.30 (10)C3B—C2B—C7B119.71 (11)
C8—C7—C6118.78 (10)C3B—C2B—C1B120.85 (10)
C8—C7—H7A120.6C7B—C2B—C1B119.37 (10)
C6—C7—H7A120.6C4B—C3B—C2B120.03 (12)
C7—C8—C3121.73 (10)C4B—C3B—H3BA120.0
C7—C8—H8A119.1C2B—C3B—H3BA120.0
C3—C8—H8A119.1C5B—C4B—C3B120.10 (12)
O2—C9—H9A109.5C5B—C4B—H4BA120.0
O2—C9—H9B109.5C3B—C4B—H4BA120.0
H9A—C9—H9B109.5C4B—C5B—C6B120.11 (12)
O2—C9—H9C109.5C4B—C5B—H5BA119.9
H9A—C9—H9C109.5C6B—C5B—H5BA119.9
H9B—C9—H9C109.5C7B—C6B—C5B120.02 (12)
C2A—C1A—S1A110.33 (8)C7B—C6B—H6BA120.0
C2A—C1A—H1AA109.6C5B—C6B—H6BA120.0
S1A—C1A—H1AA109.6C6B—C7B—C2B120.03 (11)
C2A—C1A—H1AB109.6C6B—C7B—H7BA120.0
S1A—C1A—H1AB109.6C2B—C7B—H7BA120.0
H1AA—C1A—H1AB108.1
C1—N1—N2—C2−154.32 (10)C2—C3—C8—C7175.34 (10)
N2—N1—C1—S1A−173.64 (7)C1—S1A—C1A—C2A154.36 (10)
N2—N1—C1—S1B6.23 (13)S1A—C1A—C2A—C7A−101.53 (12)
C1A—S1A—C1—N15.25 (11)S1A—C1A—C2A—C3A79.84 (13)
C1A—S1A—C1—S1B−174.63 (7)C7A—C2A—C3A—C4A−0.56 (17)
C1B—S1B—C1—N1−174.67 (9)C1A—C2A—C3A—C4A178.07 (11)
C1B—S1B—C1—S1A5.21 (8)C2A—C3A—C4A—C5A−0.08 (19)
N1—N2—C2—O1−1.25 (17)C3A—C4A—C5A—C6A0.4 (2)
N1—N2—C2—C3177.27 (9)C4A—C5A—C6A—C7A−0.1 (2)
O1—C2—C3—C8−24.63 (15)C5A—C6A—C7A—C2A−0.55 (19)
N2—C2—C3—C8156.84 (10)C3A—C2A—C7A—C6A0.88 (18)
O1—C2—C3—C4151.22 (11)C1A—C2A—C7A—C6A−177.77 (11)
N2—C2—C3—C4−27.31 (15)C1—S1B—C1B—C2B−173.50 (7)
C8—C3—C4—C50.03 (17)S1B—C1B—C2B—C3B−101.80 (11)
C2—C3—C4—C5−175.77 (10)S1B—C1B—C2B—C7B74.98 (11)
C3—C4—C5—C60.60 (17)C7B—C2B—C3B—C4B0.15 (17)
C9—O2—C6—C72.19 (15)C1B—C2B—C3B—C4B176.93 (11)
C9—O2—C6—C5−177.81 (10)C2B—C3B—C4B—C5B−0.74 (19)
C4—C5—C6—O2179.43 (10)C3B—C4B—C5B—C6B0.37 (19)
C4—C5—C6—C7−0.57 (17)C4B—C5B—C6B—C7B0.58 (19)
O2—C6—C7—C8179.90 (10)C5B—C6B—C7B—C2B−1.16 (17)
C5—C6—C7—C8−0.09 (16)C3B—C2B—C7B—C6B0.79 (16)
C6—C7—C8—C30.75 (17)C1B—C2B—C7B—C6B−176.03 (10)
C4—C3—C8—C7−0.72 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6A—H6AA···O1i0.952.413.2516 (17)147
C1B—H1BA···O1ii0.992.353.2872 (16)157
C3B—H3BA···O1iii0.952.673.5351 (18)152
C6B—H6BA···O2iv0.952.473.4173 (17)174
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x−1, y, z; (iv) −x+1, −y+2, −z−1.

Experimental details

Crystal data
Chemical formulaC23H22N2O2S2
Mr422.55
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)9.838 (2), 9.845 (2), 11.307 (2)
α, β, γ (°)70.25 (3), 90.00 (3), 89.37 (3)
V (Å3)1030.6 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.28
Crystal size (mm)0.30 × 0.26 × 0.22
Data collection
DiffractometerBruker APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.921, 0.941
No. of measured, independent and
observed [I > 2σ(I)] reflections		12424, 6210, 5954
Rint0.015
(sin θ/λ)max (Å−1)0.715
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.098, 1.06
No. of reflections6210
No. of parameters263
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.56, −0.35

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6A—H6AA···O1i0.952.413.2516 (17)146.8
C1B—H1BA···O1ii0.992.353.2872 (16)156.6
C3B—H3BA···O1iii0.952.673.5351 (18)152.2
C6B—H6BA···O2iv0.952.473.4173 (17)173.9
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x−1, y, z; (iv) −x+1, −y+2, −z−1.
 

Acknowledgements

SKK thanks the DST, New Delhi, India, for the award of a Young Scientist Fellowship (No. SR/FTP/CS-35/2005). RJB acknowledges the Laboratory for the Structure of Matter at the Naval Research Laboratory for access to their diffractometers.

References

First citationBharti, N., Maurya, M. R., Naqvi, F., Bhattcharya, A., Bhattacharya, S. & Azam, A. (2000). Eur. J. Med. Chem. 35, 481–486.  Web of Science PubMed Google Scholar
 First citationBoschi, A., Bolzati, C., Uccelli, L. & Duatti, A. (2003). Nucl. Med. Biol. 30, 381–387.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA, 2006.  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 citationSingh, N. K., Singh, M. & Butcher, R. J. (2007). Acta Cryst. E63, o4405.  Web of Science CSD CrossRef 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 66| Part 8| August 2010| Page o1899
https://doi.org/10.1107/S1600536810025389
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