Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Previous article cross.png
Next article cross.png
Previous article cross.png
Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Next article cross.png

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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 2| February 2016| x160190
https://doi.org/10.1107/S2414314616001905

Benzyl 3-(3,4,5-tri­meth­­oxy­benzyl­­idene)di­thio­carbazate

CROSSMARK_Color_square_no_text.svg
M. A. A. A. A. Islam,a M. C. Sheikh,b A. A. Mahmud,a R. Miyatakec* and E. Zangrandod

aDepartment of Chemistry, Rajshahi University of Engineering & Technology, Rajshahi 6204, Bangladesh, bDepartment of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, cCenter for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, and dDepartment of Chemical and Pharmaceutical Sciences, via Giorgieri 1, 34127 Trieste, Italy
*Correspondence e-mail: miyatake@ctg.u-toyama.ac.jp

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 9 January 2016; accepted 1 February 2016; online 10 February 2016)

The title compound, C18H20N2O3S2, a di­thio­carbazate derivative, adopts an E conformation about the C=N bond. The tri­meth­oxy­phenyl group and the di­thio­carbazate fragment lie almost in the same plane, with the mean plane of the di­thio­carbazate unit being inclined to the tri­meth­oxy­phenyl ring by 13.34 (6)°. The aromatic rings are inclined to one another by 75.30 (9)°. In the crystal, mol­ecules are linked via pairs of N—H⋯S hydrogen bonds, forming inversion dimers with an R22(8) ring motif. The dimers are linked via C—H⋯O hydrogen bonds, forming undulating sheets lying parallel to (103) which are linked via C—H⋯π inter­actions, forming a three-dimensional supra­molecular structure.

CCDC reference: 1434503

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

There has been immense inter­est on nitro­gen–sulfur donor ligands since the report on S-benzyl­dithio­carbazate (SBDTC) (Ali & Tarafder, 1977[Ali, M. A. & Tarafder, M. T. H. (1977). J. Inorg. Nucl. Chem. 39, 1785-1791.]). The versatile coordination chemistry and increasingly important biological properties of ligands derived from SBDTC have also received much attention (Ali et al., 2001[Akbar Ali, M., Mirza, A. H., Butcher, R. J., Tarafder, M. T. H. & Ali, M. A. (2001). Inorg. Chim. Acta, 320, 1-6.], 2002[Akbar Ali, M., Mirza, A. H., Butcher, R. J., Tarafder, M. T. H., Keat, T. B. & Ali, M. A. (2002). J. Inorg. Biochem. 92, 141-148.]; Crouse et al., 2004[Crouse, K. A., Chew, K. B., Tarafder, M. T. H., Kasbollah, A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2004). Polyhedron, 23, 161-168.], Tarafder et al., 2001[Tarafder, M. T. H., Kasbollah, A., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2001). Polyhedron, 20, 2363-2370.]). The synthesis and structure of SBDTC has been reported previously (Ali & Tarafder, 1977[Ali, M. A. & Tarafder, M. T. H. (1977). J. Inorg. Nucl. Chem. 39, 1785-1791.]). In a continuation of our research in this field, the title potentially bidentate (NS) Schiff base was synthesized and its crystal structure is reported on herein.

The mol­ecular structure of the title compound is illustrated in Fig. 1[link]. The geometric details are similar to those in two closely related compounds, namely benzyl (E)-3(4-meth­oxy­benzyl­idene)di­thio­carbazate (Fan et al., 2011[Fan, Z., Huang, Y.-L., Wang, Z., Guo, H.-Q. & Shan, S. (2011). Acta Cryst. E67, o3011.]) and benzyl 2-(3,4-di­meth­oxy­benzyl­idene)di­thio­carbazate (Tan et al., 2015[Tan, Y.-F., Break, M. K. bin, Tahir, M. I. M. & Khoo, T.-J. (2015). Acta Cryst. E71, 238-240.]). The essential difference being the dihedral angle between the two aromatic rings; 85.7 (3)° in the first and 65.59 (8) and 73.10 (8)° in the second compound (Z′ = 2). In the title compound this dihedral angle is 75.30 (9)°.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom labelling.

In the crystal, inversion dimers are formed with mol­ecules being linked via pairs of N—H⋯S hydrogen bonds (Table 1[link] and Fig. 2[link]). The dimers are linked via C—H⋯O hydrogen bonds, forming undulating sheets parallel to (103); see Fig. 2[link] and Table 1[link], which in turn are linked by C—H⋯π inter­actions forming a three-dimensional supra­molecular structure (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C15 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H8⋯S2i 0.87 (2) 2.52 (2) 3.381 (2) 169 (2)
C16—H14⋯O3ii 0.98 2.41 3.191 (2) 137
C18—H18⋯Cg2iii 0.98 2.80 3.668 (2) 148
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x-1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].
[Figure 2]
Figure 2
The crystal packing of the title compound, viewed along the a axis. The hydrogen bonds are shown as dashed lines (Table 1[link]).

Synthesis and crystallization

The ligand precursor, S-benzyl di­thio­carbazate (SBDTC) was prepared by a literature method (Ali & Tarafder, 1977[Ali, M. A. & Tarafder, M. T. H. (1977). J. Inorg. Nucl. Chem. 39, 1785-1791.]). The title Schiff base was prepared by adding the ligand precursor, SBDTC (0.99 g, 5 mmol) dissolved in ethanol (40 ml), to a solution of 3,4,5-trimeth­oxy benzaldehyde (0.98 g, 5 mmol) in ethanol (10 ml) and the mixture was heated under reflux for 1 h. The light yellow precipitate that formed was filtered off, washed with hot ethanol and dried under vacuum over anhydrous CaCl2 (yield: 1.10 g, 56%). 175 mg of the title compound were dissolved in ethanol (15 ml) on warming and the resulting yellow solution was allowed to stand at room temperature for slow evaporation of the solvent. Yellow plate-like single crystals were obtained after 15 days (m.p. 431–432 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C18H20N2O3S2
Mr 376.49
Crystal system, space group Monoclinic, P21/c
Temperature (K) 173
a, b, c (Å) 6.24258 (11), 11.4063 (2), 26.2386 (5)
β (°) 90.1171 (7)
V (Å3) 1868.31 (6)
Z 4
Radiation type Cu Kα
μ (mm−1) 2.75
Crystal size (mm) 0.35 × 0.28 × 0.19
 
Data collection
Diffractometer Rigaku R-AXIS RAPID
Absorption correction Multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.506, 0.593
No. of measured, independent and observed [F2 > 2.0σ(F2)] reflections 21554, 3432, 3235
Rint 0.062
(sin θ/λ)max (Å−1) 0.602
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.098, 1.06
No. of reflections 3432
No. of parameters 230
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.33, −0.30
Computer programs: RAPID-AUTO (Rigaku, 2001[Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]), SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), 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.]), CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Structural data

CCDC reference: 1434503

Crystal structure: contains datablocks Global, I. DOI: https://doi.org/10.1107/S2414314616001905/su5273sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616001905/su5273Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616001905/su5273Isup3.cml

checkCIF report


Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010) and Mercury (Macrae et al., 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Benzyl 3-(3,4,5-trimethoxybenzylidene)dithiocarbazate top
Crystal data top
C18H20N2O3S2F(000) = 792.00
Mr = 376.49Dx = 1.338 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybcCell parameters from 21153 reflections
a = 6.24258 (11) Åθ = 3.4–68.3°
b = 11.4063 (2) ŵ = 2.75 mm−1
c = 26.2386 (5) ÅT = 173 K
β = 90.1171 (7)°Prism, colorless
V = 1868.31 (6) Å30.35 × 0.28 × 0.19 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3235 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.062
ω scansθmax = 68.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −7→7
Tmin = 0.506, Tmax = 0.593k = −13→13
21554 measured reflectionsl = −31→31
3432 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0523P)2 + 0.7342P]
where P = (Fo2 + 2Fc2)/3
3432 reflections(Δ/σ)max = 0.002
230 parametersΔρmax = 0.33 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methods
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full convariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; corrections between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.58993 (6)0.32030 (3)0.572138 (14)0.02876 (13)
S20.72890 (6)0.14497 (4)0.492037 (15)0.03325 (14)
O1−0.57057 (17)−0.00200 (10)0.68375 (4)0.0312 (3)
O2−0.4893 (2)0.16929 (11)0.75534 (5)0.0424 (4)
O3−0.1411 (2)0.29687 (12)0.75144 (5)0.0407 (3)
N10.3850 (2)0.12935 (12)0.54866 (5)0.0274 (3)
N20.2535 (2)0.16318 (11)0.58823 (5)0.0260 (3)
C10.8673 (3)0.50012 (15)0.56699 (6)0.0308 (4)
C20.7383 (3)0.59440 (16)0.55381 (7)0.0378 (4)
C30.7714 (3)0.70419 (16)0.57498 (7)0.0410 (5)
C40.9326 (3)0.72065 (16)0.60977 (8)0.0430 (5)
C51.0614 (4)0.62829 (18)0.62351 (9)0.0524 (6)
C61.0298 (3)0.51833 (16)0.60222 (8)0.0432 (5)
C70.8316 (3)0.38117 (15)0.54361 (7)0.0355 (4)
C80.5593 (3)0.19103 (13)0.53718 (6)0.0257 (4)
C90.0923 (3)0.09592 (13)0.59562 (6)0.0256 (4)
C10−0.0568 (3)0.11515 (13)0.63747 (6)0.0242 (3)
C11−0.2397 (3)0.04602 (13)0.63982 (6)0.0243 (3)
C12−0.3865 (3)0.06133 (13)0.67907 (6)0.0253 (4)
C13−0.3489 (3)0.14652 (14)0.71643 (6)0.0289 (4)
C14−0.1638 (3)0.21614 (14)0.71337 (6)0.0293 (4)
C15−0.0170 (3)0.20056 (14)0.67457 (6)0.0277 (4)
C16−0.5848 (3)−0.10738 (15)0.65484 (6)0.0337 (4)
C17−0.5539 (4)0.0735 (2)0.78659 (7)0.0519 (6)
C180.0391 (3)0.37378 (17)0.74869 (7)0.0425 (5)
H10.62560.58350.52990.0454*
H20.68240.76810.56540.0492*
H30.95520.79590.62440.0516*
H41.17280.63980.64770.0629*
H51.12020.45500.61180.0518*
H60.95570.32950.55060.0426*
H70.81370.38830.50620.0426*
H80.361 (3)0.0623 (19)0.5340 (8)0.034 (5)*
H90.06920.03170.57320.0308*
H10−0.2647−0.01200.61450.0291*
H110.10900.24710.67310.0332*
H12−0.4516−0.15200.65860.0404*
H13−0.6075−0.08820.61880.0404*
H14−0.7053−0.15450.66720.0404*
H15−0.43180.02100.79220.0623*
H16−0.66970.03040.76970.0623*
H17−0.60460.10330.81950.0623*
H180.02940.43250.77580.0511*
H190.04030.41310.71550.0511*
H200.17130.32840.75290.0511*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0311 (3)0.0264 (3)0.0288 (3)−0.00276 (14)0.00610 (16)−0.00455 (15)
S20.0329 (3)0.0374 (3)0.0295 (3)−0.00612 (16)0.01092 (17)−0.00980 (16)
O10.0283 (6)0.0331 (6)0.0321 (6)−0.0073 (5)0.0059 (5)−0.0062 (5)
O20.0412 (7)0.0421 (7)0.0439 (8)−0.0058 (6)0.0220 (6)−0.0138 (6)
O30.0415 (7)0.0441 (7)0.0365 (7)−0.0143 (6)0.0117 (6)−0.0202 (6)
N10.0299 (7)0.0280 (7)0.0243 (7)−0.0036 (6)0.0056 (6)−0.0062 (6)
N20.0283 (7)0.0282 (7)0.0216 (7)0.0010 (6)0.0038 (5)−0.0019 (5)
C10.0303 (8)0.0288 (8)0.0335 (9)−0.0043 (7)0.0060 (7)0.0018 (7)
C20.0383 (10)0.0370 (10)0.0381 (10)0.0012 (8)−0.0076 (8)−0.0010 (8)
C30.0447 (10)0.0307 (9)0.0477 (11)0.0056 (8)−0.0013 (9)0.0028 (8)
C40.0445 (11)0.0290 (9)0.0554 (12)−0.0067 (8)−0.0010 (9)−0.0053 (9)
C50.0447 (11)0.0433 (11)0.0691 (14)−0.0053 (9)−0.0210 (10)−0.0059 (10)
C60.0373 (10)0.0324 (10)0.0598 (12)0.0008 (8)−0.0102 (9)0.0036 (9)
C70.0327 (9)0.0323 (9)0.0415 (10)−0.0056 (7)0.0109 (8)−0.0037 (8)
C80.0283 (8)0.0290 (8)0.0198 (7)−0.0007 (6)−0.0002 (6)−0.0007 (6)
C90.0279 (8)0.0256 (8)0.0235 (8)0.0007 (6)0.0010 (6)−0.0019 (6)
C100.0254 (8)0.0239 (7)0.0232 (7)0.0025 (6)0.0006 (6)0.0005 (6)
C110.0281 (8)0.0224 (7)0.0223 (7)0.0011 (6)0.0004 (6)−0.0015 (6)
C120.0234 (7)0.0258 (8)0.0265 (8)−0.0003 (6)0.0001 (6)0.0010 (6)
C130.0284 (8)0.0308 (9)0.0275 (8)0.0007 (7)0.0068 (7)−0.0047 (7)
C140.0311 (8)0.0293 (8)0.0274 (8)−0.0020 (7)0.0021 (7)−0.0073 (7)
C150.0261 (8)0.0294 (8)0.0275 (8)−0.0030 (6)0.0018 (6)−0.0030 (7)
C160.0372 (9)0.0330 (9)0.0310 (9)−0.0121 (7)0.0031 (7)−0.0035 (7)
C170.0575 (13)0.0635 (14)0.0347 (10)−0.0193 (11)0.0176 (9)−0.0105 (10)
C180.0431 (11)0.0448 (11)0.0398 (10)−0.0144 (9)0.0053 (8)−0.0178 (9)
Geometric parameters (Å, º) top
S1—C71.8229 (18)C12—C131.400 (3)
S1—C81.7468 (16)C13—C141.404 (3)
S2—C81.6748 (16)C14—C151.383 (3)
O1—C121.3632 (19)N1—H80.87 (2)
O1—C161.424 (2)C2—H10.950
O2—C131.372 (2)C3—H20.950
O2—C171.425 (3)C4—H30.950
O3—C141.366 (2)C5—H40.950
O3—C181.429 (3)C6—H50.950
N1—N21.3798 (19)C7—H60.990
N1—C81.331 (2)C7—H70.990
N2—C91.281 (2)C9—H90.950
C1—C21.387 (3)C11—H100.950
C1—C61.387 (3)C15—H110.950
C1—C71.505 (3)C16—H120.980
C2—C31.385 (3)C16—H130.980
C3—C41.370 (3)C16—H140.980
C4—C51.373 (3)C17—H150.980
C5—C61.387 (3)C17—H160.980
C9—C101.457 (3)C17—H170.980
C10—C111.389 (2)C18—H180.980
C10—C151.399 (3)C18—H190.980
C11—C121.391 (3)C18—H200.980
S1···N22.7936 (14)C16···H9iv3.4278
S1···C23.2963 (19)C16···H17iii3.5696
S2···C73.0818 (18)C16···H18iii3.3523
O1···O22.7567 (17)C17···H4x3.0305
O1···C172.834 (3)C17···H12v3.4452
O2···O32.6179 (19)C17···H19iii3.5451
N2···C152.860 (2)C17···H20iv3.4889
C1···C42.784 (3)C18···H3x3.4471
C2···C52.747 (3)C18···H12vii3.5514
C3···C62.757 (3)C18···H14v3.0549
C8···C93.471 (3)C18···H15vii3.1606
C10···C132.786 (3)C18···H16v2.9559
C11···C142.777 (3)H1···S1viii3.1884
C11···C162.804 (3)H1···C7viii3.4647
C12···C152.803 (3)H1···C8viii3.3216
C12···C173.014 (3)H1···H1viii2.9226
C14···C173.505 (3)H1···H6xi3.5063
C15···C182.794 (3)H1···H7viii2.9175
S2···N1i3.3813 (15)H2···S2viii3.1351
S2···C9ii3.5806 (16)H2···N1viii3.2393
O1···O3iii3.3774 (18)H2···C8viii3.1173
O1···N2iv3.3205 (17)H2···C16xii3.2138
O1···C9iv3.3173 (19)H2···H8viii3.2579
O1···C10iv3.5294 (18)H2···H10xii2.8401
O2···C16v3.500 (2)H2···H12xii2.7423
O3···O1v3.3774 (18)H2···H13xii2.8181
O3···C16v3.191 (2)H2···H17vii3.5924
N1···S2i3.3813 (15)H3···O3xiv3.4567
N1···C11ii3.477 (2)H3···C11xii3.1286
N2···O1ii3.3205 (17)H3···C16xiii3.1770
N2···C12ii3.473 (2)H3···C18xiv3.4471
C8···C11ii3.398 (3)H3···H9xii3.0905
C9···S2iv3.5806 (16)H3···H10xii2.5989
C9···O1ii3.3173 (19)H3···H12xii2.7598
C9···C16ii3.441 (3)H3···H13xiii3.0378
C10···O1ii3.5294 (18)H3···H14xiii2.4634
C11···N1iv3.477 (2)H3···H17vii3.4347
C11···C8iv3.398 (3)H3···H18xiv3.0487
C12···N2iv3.473 (2)H3···H20xiv3.3387
C12···C18vi3.585 (3)H4···O2xiv3.2350
C16···O2iii3.500 (2)H4···O3xiv3.2021
C16···O3iii3.191 (2)H4···C16xiii3.2619
C16···C9iv3.441 (3)H4···C17xiv3.0305
C18···C12vii3.585 (3)H4···H12xiii3.3486
S1···H13.2085H4···H13xiii3.4773
S1···H83.42 (2)H4···H14xiii2.5194
S2···H62.9641H4···H15xiv2.6321
S2···H72.8496H4···H17xiv2.8585
S2···H82.72 (2)H4···H19ii3.2460
O1···H102.6408H5···S1ii3.4726
O1···H152.9831H5···N2ii3.4872
O1···H162.3678H5···C15ii3.4458
O3···H112.6448H5···H11ii2.8662
N1···H92.3550H5···H15xiv3.2679
N2···H112.5887H5···H19ii2.8073
C1···H23.2671H6···N1ii3.5208
C1···H43.2629H6···N2ii2.8329
C2···H33.2452H6···C2xi3.4527
C2···H53.2422H6···C9ii3.0365
C2···H63.3133H6···C10ii3.3446
C2···H72.7037H6···C15ii3.5747
C3···H43.2316H6···H1xi3.5063
C4···H13.2396H6···H9ii3.5202
C4···H53.2486H6···H11ii3.4827
C5···H23.2332H7···C1xi3.0486
C6···H13.2409H7···C2xi3.2187
C6···H33.2523H7···C3xi3.5191
C6···H62.5858H7···C5xi3.4992
C6···H73.2170H7···C6xi3.1936
C7···H12.6665H7···H1viii2.9175
C7···H52.6731H7···H7xi3.4664
C8···H62.9563H8···S2i2.52 (2)
C8···H72.8719H8···N1i3.47 (2)
C9···H82.36 (2)H8···C8i3.48 (2)
C9···H102.5943H8···H2viii3.2579
C9···H112.6686H8···H8i2.87 (3)
C11···H92.6104H8···H10ii3.2598
C11···H113.2801H8···H13ii2.8170
C11···H122.6643H9···S2iv3.2710
C11···H132.8124H9···S2i2.9309
C12···H122.5252H9···C16ii3.4278
C12···H132.7018H9···H3xv3.0905
C12···H143.1803H9···H6iv3.5202
C12···H153.0164H9···H13ii2.7142
C12···H162.9863H9···H14ii3.5445
C13···H103.2712H10···N1iv3.2172
C13···H113.2851H10···C3xv3.4074
C13···H152.5039H10···C4xv3.2917
C13···H162.7799H10···C8iv3.2674
C13···H173.1809H10···H2xv2.8401
C14···H153.4698H10···H3xv2.5989
C14···H183.1977H10···H8iv3.2598
C14···H192.5834H10···H18vi3.2894
C14···H202.6612H11···O1ii3.4859
C15···H93.3282H11···O2ii3.4215
C15···H103.2774H11···H5iv2.8662
C15···H192.6753H11···H6iv3.4827
C15···H202.7782H12···O2iii3.0650
C16···H102.5114H12···O3iii3.5216
C16···H163.4400H12···C3xv3.0744
C18···H112.4922H12···C4xv3.0845
H1···H22.3281H12···C17iii3.4452
H1···H63.5962H12···C18vi3.5514
H1···H72.5940H12···H2xv2.7423
H2···H32.3210H12···H3xv2.7598
H3···H42.3212H12···H4xvi3.3486
H4···H52.3311H12···H17iii2.8711
H5···H62.3833H12···H18vi3.2897
H5···H73.4487H12···H20vi2.9146
H8···H92.1210H13···S2ix3.0738
H9···H102.4034H13···N1iv3.0897
H10···H122.2929H13···N2iv3.1005
H10···H132.3124H13···C3xv3.5410
H10···H143.4837H13···C9iv2.8789
H11···H183.4621H13···H2xv2.8181
H11···H192.2374H13···H3xvi3.0378
H11···H202.3203H13···H4xvi3.4773
H14···H163.4230H13···H8iv2.8170
S1···H1viii3.1884H13···H9iv2.7142
S1···H5iv3.4726H14···O2iii3.1039
S2···H2viii3.1351H14···O3iii2.4062
S2···H8i2.52 (2)H14···C4xvi3.0657
S2···H9ii3.2710H14···C5xvi3.0935
S2···H9i2.9309H14···C14iii3.5597
S2···H13ix3.0738H14···C18iii3.0549
O1···H11iv3.4859H14···H3xvi2.4634
O1···H18iii3.1461H14···H4xvi2.5194
O1···H20vi3.5641H14···H9iv3.5445
O2···H4x3.2350H14···H17iii3.3907
O2···H11iv3.4215H14···H18iii2.7060
O2···H12v3.0650H14···H20iii3.5948
O2···H14v3.1039H15···C5x3.4234
O2···H20iv2.7905H15···C18vi3.1606
O3···H3x3.4567H15···H4x2.6321
O3···H4x3.2021H15···H5x3.2679
O3···H12v3.5216H15···H18vi3.2450
O3···H14v2.4062H15···H19vi2.7444
O3···H16v2.9656H15···H20vi2.9788
N1···H2viii3.2393H16···O3iii2.9656
N1···H6iv3.5208H16···C18iii2.9559
N1···H8i3.47 (2)H16···H18iii2.7751
N1···H10ii3.2172H16···H19iii2.7012
N1···H13ii3.0897H16···H20iv3.5682
N2···H5iv3.4872H17···C2vi3.4315
N2···H6iv2.8329H17···C3vi3.1767
N2···H13ii3.1005H17···C4vi3.0736
C1···H7xi3.0486H17···C5vi3.2357
C2···H6xi3.4527H17···C6vi3.4971
C2···H7xi3.2187H17···C16v3.5696
C2···H17vii3.4315H17···H2vi3.5924
C3···H7xi3.5191H17···H3vi3.4347
C3···H10xii3.4074H17···H4x2.8585
C3···H12xii3.0744H17···H12v2.8711
C3···H13xii3.5410H17···H14v3.3907
C3···H17vii3.1767H17···H19iii3.5960
C4···H10xii3.2917H17···H20iv3.4050
C4···H12xii3.0845H18···O1v3.1461
C4···H14xiii3.0657H18···C10vii3.0889
C4···H17vii3.0736H18···C11vii2.8786
C5···H7xi3.4992H18···C12vii2.9183
C5···H14xiii3.0935H18···C13vii3.1582
C5···H15xiv3.4234H18···C14vii3.3538
C5···H17vii3.2357H18···C15vii3.3236
C5···H19ii3.4448H18···C16v3.3523
C6···H7xi3.1936H18···H3x3.0487
C6···H17vii3.4971H18···H10vii3.2894
C6···H19ii3.2057H18···H12vii3.2897
C7···H1viii3.4647H18···H14v2.7060
C8···H1viii3.3216H18···H15vii3.2450
C8···H2viii3.1173H18···H16v2.7751
C8···H8i3.48 (2)H19···C5iv3.4448
C8···H10ii3.2674H19···C6iv3.2057
C9···H6iv3.0365H19···C17v3.5451
C9···H13ii2.8789H19···H4iv3.2460
C10···H6iv3.3446H19···H5iv2.8073
C10···H18vi3.0889H19···H15vii2.7444
C11···H3xv3.1286H19···H16v2.7012
C11···H18vi2.8786H19···H17v3.5960
C12···H18vi2.9183H20···O1vii3.5641
C12···H20vi3.4701H20···O2ii2.7905
C13···H18vi3.1582H20···C12vii3.4701
C14···H14v3.5597H20···C17ii3.4889
C14···H18vi3.3538H20···H3x3.3387
C15···H5iv3.4458H20···H12vii2.9146
C15···H6iv3.5747H20···H14v3.5948
C15···H18vi3.3236H20···H15vii2.9788
C16···H2xv3.2138H20···H16ii3.5682
C16···H3xvi3.1770H20···H17ii3.4050
C16···H4xvi3.2619
C7—S1—C8101.28 (8)C2—C3—H2120.003
C12—O1—C16116.82 (12)C4—C3—H2120.015
C13—O2—C17117.73 (15)C3—C4—H3120.045
C14—O3—C18117.24 (14)C5—C4—H3120.035
N2—N1—C8120.69 (13)C4—C5—H4119.829
N1—N2—C9114.53 (13)C6—C5—H4119.825
C2—C1—C6118.27 (16)C1—C6—H5119.752
C2—C1—C7120.79 (15)C5—C6—H5119.769
C6—C1—C7120.93 (16)S1—C7—H6110.240
C1—C2—C3121.00 (17)S1—C7—H7110.252
C2—C3—C4119.98 (18)C1—C7—H6110.244
C3—C4—C5119.92 (18)C1—C7—H7110.254
C4—C5—C6120.3 (2)H6—C7—H7108.526
C1—C6—C5120.48 (18)N2—C9—H9119.100
S1—C7—C1107.33 (12)C10—C9—H9119.090
S1—C8—S2124.58 (10)C10—C11—H10119.857
S1—C8—N1114.58 (12)C12—C11—H10119.853
S2—C8—N1120.84 (12)C10—C15—H11120.507
N2—C9—C10121.81 (14)C14—C15—H11120.505
C9—C10—C11118.31 (14)O1—C16—H12109.465
C9—C10—C15121.09 (14)O1—C16—H13109.476
C11—C10—C15120.61 (15)O1—C16—H14109.460
C10—C11—C12120.29 (14)H12—C16—H13109.474
O1—C12—C11123.84 (14)H12—C16—H14109.472
O1—C12—C13116.42 (14)H13—C16—H14109.481
C11—C12—C13119.74 (14)O2—C17—H15109.473
O2—C13—C12123.10 (14)O2—C17—H16109.471
O2—C13—C14117.55 (14)O2—C17—H17109.471
C12—C13—C14119.30 (15)H15—C17—H16109.469
O3—C14—C13115.07 (14)H15—C17—H17109.466
O3—C14—C15123.85 (15)H16—C17—H17109.477
C13—C14—C15121.07 (15)O3—C18—H18109.471
C10—C15—C14118.99 (15)O3—C18—H19109.469
N2—N1—H8118.4 (13)O3—C18—H20109.466
C8—N1—H8120.5 (13)H18—C18—H19109.475
C1—C2—H1119.507H18—C18—H20109.476
C3—C2—H1119.494H19—C18—H20109.470
C7—S1—C8—S22.22 (13)C3—C4—C5—C60.2 (3)
C7—S1—C8—N1−177.12 (11)C4—C5—C6—C1−0.3 (3)
C8—S1—C7—C1174.88 (10)N2—C9—C10—C11173.37 (13)
C16—O1—C12—C1116.4 (2)N2—C9—C10—C15−6.9 (3)
C16—O1—C12—C13−164.06 (12)C9—C10—C11—C12−179.97 (12)
C17—O2—C13—C1254.5 (2)C9—C10—C15—C14179.56 (13)
C17—O2—C13—C14−128.19 (15)C11—C10—C15—C14−0.7 (3)
C18—O3—C14—C13−177.01 (13)C15—C10—C11—C120.3 (3)
C18—O3—C14—C154.0 (3)C10—C11—C12—O1179.28 (13)
N2—N1—C8—S1−5.15 (19)C10—C11—C12—C13−0.2 (3)
N2—N1—C8—S2175.48 (11)O1—C12—C13—O2−1.7 (3)
C8—N1—N2—C9−179.43 (12)O1—C12—C13—C14−178.96 (12)
N1—N2—C9—C10176.75 (12)C11—C12—C13—O2177.85 (13)
C2—C1—C6—C5−0.0 (3)C11—C12—C13—C140.6 (3)
C6—C1—C2—C30.4 (3)O2—C13—C14—O32.5 (2)
C2—C1—C7—S1−73.33 (18)O2—C13—C14—C15−178.45 (13)
C7—C1—C2—C3−179.58 (14)C12—C13—C14—O3179.90 (13)
C6—C1—C7—S1106.70 (17)C12—C13—C14—C15−1.0 (3)
C7—C1—C6—C5179.95 (15)O3—C14—C15—C10−179.93 (13)
C1—C2—C3—C4−0.5 (3)C13—C14—C15—C101.1 (3)
C2—C3—C4—C50.1 (3)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z; (iii) −x−1, y−1/2, −z+3/2; (iv) x−1, y, z; (v) −x−1, y+1/2, −z+3/2; (vi) −x, y−1/2, −z+3/2; (vii) −x, y+1/2, −z+3/2; (viii) −x+1, −y+1, −z+1; (ix) −x, −y, −z+1; (x) −x+1, y−1/2, −z+3/2; (xi) −x+2, −y+1, −z+1; (xii) x+1, y+1, z; (xiii) x+2, y+1, z; (xiv) −x+1, y+1/2, −z+3/2; (xv) x−1, y−1, z; (xvi) x−2, y−1, z.
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C10–C15 ring.
D—H···AD—HH···AD···AD—H···A
N1—H8···S2i0.87 (2)2.52 (2)3.381 (2)169 (2)
C16—H14···O3iii0.982.413.191 (2)137
C18—H18···Cg2vii0.982.803.668 (2)148
Symmetry codes: (i) −x+1, −y, −z+1; (iii) −x−1, y−1/2, −z+3/2; (vii) −x, y+1/2, −z+3/2.
 

Acknowledgements

MAAAAI and AAM are grateful to the Department of Chemistry, Rajshahi University of Engineering & Technology (RUET), for the provision of laboratory facilities. MCS and RM acknowledge the Department of Applied Chemistry, Faculty of Engineering, University of Toyama, Japan, and Center for Environmental Conservation and Research Safety, University of Toyama, Japan, respectively, for providing facilities for single-crystal X-ray analyses.

References

First citationAkbar Ali, M., Mirza, A. H., Butcher, R. J., Tarafder, M. T. H. & Ali, M. A. (2001). Inorg. Chim. Acta, 320, 1–6.  CSD CrossRef CAS Google Scholar
 First citationAkbar Ali, M., Mirza, A. H., Butcher, R. J., Tarafder, M. T. H., Keat, T. B. & Ali, M. A. (2002). J. Inorg. Biochem. 92, 141–148.  CSD CrossRef PubMed CAS Google Scholar
 First citationAli, M. A. & Tarafder, M. T. H. (1977). J. Inorg. Nucl. Chem. 39, 1785–1791.  Google Scholar
 First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals Google Scholar
 First citationCrouse, K. A., Chew, K. B., Tarafder, M. T. H., Kasbollah, A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2004). Polyhedron, 23, 161–168.  Web of Science CSD CrossRef CAS Google Scholar
 First citationFan, Z., Huang, Y.-L., Wang, Z., Guo, H.-Q. & Shan, S. (2011). Acta Cryst. E67, o3011.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationMacrae, 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.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationRigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTan, Y.-F., Break, M. K. bin, Tahir, M. I. M. & Khoo, T.-J. (2015). Acta Cryst. E71, 238–240.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationTarafder, M. T. H., Kasbollah, A., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2001). Polyhedron, 20, 2363–2370.  Web of Science CSD CrossRef CAS 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 logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 2| February 2016| x160190
https://doi.org/10.1107/S2414314616001905
Follow IUCr Journals
Sign up for e-alerts
E-alerts
Follow IUCr on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS