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 3| March 2016| x160453
doi:10.1107/S2414314616004533

2-({5-[(4-Chloro­phen­­oxy)­meth­yl]-4-phenyl-4H-1,2,4-triazol-3-yl}sulfan­yl)-N-phenyl­acetamide

Joel T. Mague,a Shaaban K. Mohamed,b,c Mehmet Akkurt,d Etify A. Bakhitee and Mustafa R. Albayatif*

aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, eChemistry Department, Faculty of Science, Assiut University, Assiut 71516, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 8 March 2016; accepted 16 March 2016; online 31 March 2016)

The title mol­ecule, C23H19ClN4O2S, is in an `extended' conformation. In the crystal, pairwise N—H⋯N and C—H⋯O hydrogen bonds lead to the formation of `stair-step' chains. C—H⋯π inter­actions further contribute to the consolidation of the mol­ecular packing. The 4-chloro­phenyl group is disordered over two sets of sites in a 0.948 (2):0.052 (2) ratio. The dihedral angle between the two components of the disordered chloro-substituted benzene ring is 15.76 (9) °.

CCDC reference: 1468942

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

Structure description

In the last few years, the chemistry of 1,2,4-triazoles has received considerable attention owing to their synthetic and effective biological importance (Shaker, 2006[Shaker, R. M. (2006). ARKIVOC, ix, 59-112.]). Many triazole compounds exhibited different biological properties such as anti­fungal, anti-bacterial, anti-inflammatory, ant-cancer, anti-malarial and analgesic activity (Bektaş et al., 2010[Bektaş, H., Karaali, N., Şahin, D., Demirbaş, A., Karaoglu, S. A., Şengül, A. & Demirbaş, N. (2010). Molecules, 15, 2427-2438.]; Jawad et al., 2012[Jawad, A. H., Shneine, J. K., Ahmed, A. & Abdulrasool, M. M. (2012). Int. J. Re. Pharm. Chem. (IJRPC), 2, 1109-1123.]; Singhal et al., 2011[Singhal, N., Sharma, P. K., Dudhe, R. & Kumar, N. (2011). J. Chem. Pharm. Res. 3, 126-133.]).

In the solid state, the mol­ecule of the title compound (Fig. 1[link]) is in an `extended' conformation. The 1,2,4-triazole ring (N1–N3/C8/C9) forms dihedral angles of 62.57 (8) and 33.48 (8)°, with the phenyl ring (C10–C15) attached to the 1,2,4-triazol ring and the phenyl ring (C18–C23) of the N-phenyl­acetamide group, respectively. The dihedral angle between the two components of the disordered chloro-substituted benzene ring is 15.76 (9)°.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound with 50% probability ellipsoids.

In the crystal, pairwise N4—H4⋯N1i [symmetry code: (i) −x + 1, −y + 1, −z + 1] hydrogen bonds form dimers, which are then associated into `stair-step' chains through pairwise C7—H7B⋯O2ii [symmetry code: (ii) x + [{1\over 2}], y − [{1\over 2}], z] hydrogen bonds (Table 1[link] and Fig. 2[link]). In addition, C—H⋯π inter­actions are observed in the crystal structure (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C10–C15 and C18–C23 phenyl rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N4—H4⋯N1i 0.91 2.02 2.9230 (17) 174
C7—H7B⋯O2ii 0.99 2.49 3.3518 (18) 146
C3—H3⋯Cg3iii 0.95 2.92 3.867 (2) 174
C15—H15⋯Cg4iv 0.95 2.86 3.6871 (16) 146
C16—H16A⋯Cg4v 0.99 2.80 3.6488 (18) 144
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iii) -x, -y-1, -z; (iv) x, y-1, z; (v) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].
[Figure 2]
Figure 2
Packing projected onto (110). N—H⋯N and C—H⋯O hydrogen bonds are shown, respectively, as blue and purple dotted lines. Displacement ellipsoids are drawn at the 50% probability level.

Synthesis and crystallization

A suspension of 5-(4-chlorphen­oxy)methyl-4-phenyl-1,2,4-triazoline-3-thione (10 mmol), chloro­(N-phen­yl)acetamide (10 mol) and anhydrous K2CO3 (2.0 g) in dry acetone (50 ml) was heated under reflux with stirring for 3 h. The hot reaction mixture was filtered to remove K2CO3 and the clear filtrate was evaporated till dryness. The solid residue was crystallized from ethanol to give the title compound. Yield: 80%; m.p. 463 K. IR: 3300 (NH), 1670 (C=O) cm.-1 1H NMR (DMSO-d6): δ = 8.8 (s, 1H, NH), 6.5–7.8 (m, 14H, ArH), 4.9 (s, 2H, OCH2), 3.9 (s, 2H,SCH2).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The 4-chloro­phenyl group is disordered over two orientations in a 0.948 (2): 0.052 (2) ratio. The minor component was refined as a rigid hexa­gon.

Table 2
Experimental details

Crystal data
Chemical formula C23H19ClN4O2S
Mr 450.93
Crystal system, space group Monoclinic, C2/c
Temperature (K) 150
a, b, c (Å) 15.7940 (12), 11.1864 (8), 24.8212 (18)
β (°) 95.128 (1)
V (Å3) 4367.8 (6)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.30
Crystal size (mm) 0.24 × 0.20 × 0.11
 
Data collection
Diffractometer Bruker SMART APEX CCD
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.86, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections 41579, 5886, 4471
Rint 0.045
(sin θ/λ)max (Å−1) 0.686
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.118, 1.06
No. of reflections 5886
No. of parameters 287
No. of restraints 2
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.41, −0.22
Computer programs: APEX3 (Bruker, 2016[Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2016[Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]), SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data

CCDC reference: 1468942

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616004533/rz4002sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616004533/rz4002Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616004533/rz4002Isup3.cml

checkCIF report


Chemical context top

In the last few years, the chemistry of 1,2,4-triazoles has received considerable attention owing to their synthetic and effective biological importance (Shaker, 2006). Many triazole compounds exhibited different biological applications such as anti­fungal, anti-bacterial, anti-inflammatory, ant-cancer, anti-malarial and analgesic activity (Bektaş et al., 2010; Jawad et al., 2012; Singhal et al., 2011).

Structural commentary top

In the solid, the molecule (Fig. 1) is in an "extended" conformation. The 1,2,4-triazol ring (N1–N3/C8/C9) forms dihedral angles of 62.57 (8) and 33.48 (8)°, with the phenyl ring (C10—C15) attached to the 1,2,4-triazol ring and the phenyl ring (C18—C23) of the N-phenyl­acetamide group, respectively. The dihedral angle between the two components of the disordered chloro-substituted benzene ring is 15.76 (9) °.

Supra­molecular features top

Pairwise N4—H4···N1i (i: −x + 1, −y + 1, −z + 1) hydrogen bonds form dimers which are then associated into "stair-step" chains through pairwise C7—H7B···O2ii (ii: x + 1/2, y − 1/2, z) hydrogen bonds (Table 1 and Fig. 2). In addition, C—H···π inter­actions are observed in the crystal structure (Table 1).

Synthesis and crystallization top

A suspension of 5-(4-chlorphen­oxy)­methyl-4-phenyl-1,2,4-triazoline-3-thione (10 mmol), chloro­(N-phenyl)­acetamide (10 mol) and anhydrous K2CO3 (2.0 g) in dry acetone (50 ml) was heated under reflux with stirring for 3 h. The hot reaction mixture was filtered to remove K2CO3 and the clear filtrate was evaporated till dryness. The solid residue was crystallized from ethanol to give the title compound. Yield: 80%; m.p. 463 K. IR: 3300 (NH), 1670 (C=O) cm.−1 1H NMR (DMSO-d6): δ = 8.8 (s, 1H, NH), 6.5–7.8 (m, 14H, ArH), 4.9 (s, 2H, OCH2), 3.9 (s, 2H,SCH2).

Refinement top

H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 − 0.99 Å) while that attached to nitro­gen was placed in a location derived from a difference map and its coordinates adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms. The 4-chloro­phenyl group is disordered over two orientations in a 95:5 ratio. The minor component was refined as a rigid hexagon. Crystal data, data collection and structure refinement details are summarized in Table 2.

Experimental top

A suspension of 5-(4-chlorphenoxy)methyl-4-phenyl-1,2,4-triazoline-3-thione (10 mmol), chloro(N-phenyl)acetamide (10 mol) and anhydrous K2CO3 (2.0 g) in dry acetone (50 ml) was heated under reflux with stirring for 3 h. The hot reaction mixture was filtered to remove K2CO3 and the clear filtrate was evaporated till dryness. The solid residue was crystallized from ethanol to give the title compound. Yield: 80%; m.p. 463 K. IR: 3300 (NH), 1670 (C=O) cm.-1 1H NMR (DMSO-d6): δ = 8.8 (s, 1H, NH), 6.5–7.8 (m, 14H, ArH), 4.9 (s, 2H, OCH2), 3.9 (s, 2H,SCH2).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The 4-chlorophenyl group is disordered over two orientations in a 0.948 (2): 0.052 (2) ratio. The minor component was refined as a rigid hexagon.

Structure description top

In the last few years, the chemistry of 1,2,4-triazoles has received considerable attention owing to their synthetic and effective biological importance (Shaker, 2006). Many triazole compounds exhibited different biological properties such as antifungal, anti-bacterial, anti-inflammatory, ant-cancer, anti-malarial and analgesic activity (Bektaş et al., 2010; Jawad et al., 2012; Singhal et al., 2011).

In the solid state, the molecule of the title compound (Fig. 1) is in an `extended' conformation. The 1,2,4-triazole ring (N1–N3/C8/C9) forms dihedral angles of 62.57 (8) and 33.48 (8)°, with the phenyl ring (C10–C15) attached to the 1,2,4-triazol ring and the phenyl ring (C18–C23) of the N-phenylacetamide group, respectively. The dihedral angle between the two components of the disordered chloro-substituted benzene ring is 15.76 (9)°.

In the crystal, pairwise N4—H4···N1i [symmetry code: (i) −x + 1, −y + 1, −z + 1] hydrogen bonds form dimers which are then associated into `stair-step' chains through pairwise C7—H7B···O2ii [symmetry code: (ii) x + 1/2, y − 1/2, z] hydrogen bonds (Table 1 and Fig. 2). In addition, C—H···π interactions are observed in the crystal structure (Table 1).

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 50% probability ellipsoids.
[Figure 2] Fig. 2. Packing projected onto (110). N—H···N and C—H···O hydrogen bonds are shown, respectively, as blue and purple dotted lines. Displacement ellipsoids are drawn at the 50% probability level.
2-({5-[(4-Chlorophenoxy)methyl]-4-phenyl-4H-1,2,4-triazol-3-yl}sulfanyl)-N-phenylacetamide top
Crystal data top
C23H19ClN4O2SF(000) = 1872
Mr = 450.93Dx = 1.371 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 15.7940 (12) ÅCell parameters from 9935 reflections
b = 11.1864 (8) Åθ = 2.3–28.9°
c = 24.8212 (18) ŵ = 0.30 mm−1
β = 95.128 (1)°T = 150 K
V = 4367.8 (6) Å3Block, colourless
Z = 80.24 × 0.20 × 0.11 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		5886 independent reflections
Radiation source: fine-focus sealed tube4471 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 8.3333 pixels mm-1θmax = 29.2°, θmin = 1.7°
φ and ω scansh = −21→21
Absorption correction: multi-scan
(SADABS; Bruker, 2016)		k = −14→15
Tmin = 0.86, Tmax = 0.97l = −33→34
41579 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)] = 0.043Hydrogen site location: mixed
wR(F2) = 0.118H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0604P)2 + 1.3119P]
where P = (Fo2 + 2Fc2)/3
5886 reflections(Δ/σ)max < 0.001
287 parametersΔρmax = 0.41 e Å−3
2 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C23H19ClN4O2SV = 4367.8 (6) Å3
Mr = 450.93Z = 8
Monoclinic, C2/cMo Kα radiation
a = 15.7940 (12) ŵ = 0.30 mm−1
b = 11.1864 (8) ÅT = 150 K
c = 24.8212 (18) Å0.24 × 0.20 × 0.11 mm
β = 95.128 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		5886 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2016)		4471 reflections with I > 2σ(I)
Tmin = 0.86, Tmax = 0.97Rint = 0.045
41579 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0432 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.06Δρmax = 0.41 e Å−3
5886 reflectionsΔρmin = −0.21 e Å−3
287 parameters
Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = −30.00 and 210.00°. The scan time was 20 sec/frame.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 − 0.99 Å) while that attached to nitrogen was placed in a location derived from a difference map and its coordinates adjusted to give N—H = 0.91%A. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms. The 4-chlorophenyl group is disordered over two orientations in a 95:5 ratio. The minor component was refined as a rigid hexagon.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.58100 (3)−0.46695 (4)0.30292 (2)0.06539 (18)
S10.33857 (2)0.45849 (3)0.39103 (2)0.02814 (10)
O10.50609 (7)0.00496 (9)0.38890 (4)0.0346 (2)
O20.26017 (7)0.68130 (9)0.39453 (4)0.0356 (3)
N10.53671 (8)0.27205 (11)0.44169 (5)0.0323 (3)
N20.48065 (8)0.36629 (11)0.44741 (5)0.0298 (3)
N30.43815 (7)0.26509 (9)0.37347 (4)0.0226 (2)
N40.33954 (7)0.76835 (10)0.46533 (5)0.0257 (2)
H40.38020.75270.49270.031*
C10.52663 (12)−0.10073 (13)0.36507 (7)0.0287 (4)0.948 (2)
C20.60655 (11)−0.12626 (15)0.35021 (8)0.0393 (4)0.948 (2)
H20.6499−0.06720.35360.047*0.948 (2)
C30.62341 (12)−0.23890 (16)0.33017 (8)0.0452 (5)0.948 (2)
H30.6786−0.25800.32040.054*0.948 (2)
C40.55925 (12)−0.32265 (15)0.32458 (7)0.0379 (4)0.948 (2)
C50.47874 (12)−0.29637 (15)0.33764 (8)0.0410 (4)0.948 (2)
H50.4349−0.35450.33280.049*0.948 (2)
C60.46197 (11)−0.18450 (15)0.35786 (7)0.0383 (4)0.948 (2)
H60.4063−0.16510.36680.046*0.948 (2)
C1A0.5373 (18)−0.1082 (12)0.3766 (10)0.0287 (4)0.052 (2)
C2A0.5741 (17)−0.1263 (15)0.3285 (9)0.0393 (4)0.052 (2)
H2A0.5901−0.05970.30790.047*0.052 (2)
C3A0.5875 (17)−0.2418 (19)0.3104 (8)0.0452 (5)0.052 (2)
H3A0.6126−0.25420.27750.054*0.052 (2)
C4A0.5641 (19)−0.3392 (13)0.3406 (9)0.0379 (4)0.052 (2)
C5A0.5273 (16)−0.3211 (13)0.3887 (9)0.0410 (4)0.052 (2)
H5A0.5113−0.38770.40930.049*0.052 (2)
C6A0.5139 (15)−0.2056 (16)0.4068 (8)0.0383 (4)0.052 (2)
H6A0.4887−0.19320.43970.046*0.052 (2)
C70.55380 (9)0.10811 (12)0.37635 (6)0.0300 (3)
H7A0.55580.11530.33670.036*
H7B0.61280.10210.39340.036*
C80.51050 (9)0.21362 (12)0.39776 (6)0.0262 (3)
C90.42313 (8)0.36036 (11)0.40612 (5)0.0238 (3)
C100.38827 (8)0.22517 (12)0.32540 (5)0.0226 (3)
C110.37983 (10)0.29843 (13)0.28040 (6)0.0327 (3)
H110.40630.37470.28110.039*
C120.33191 (11)0.25847 (14)0.23410 (6)0.0386 (4)
H120.32470.30850.20310.046*
C130.29497 (10)0.14698 (14)0.23290 (6)0.0349 (3)
H130.26300.11990.20100.042*
C140.30446 (10)0.07439 (14)0.27815 (6)0.0339 (3)
H140.2793−0.00280.27710.041*
C150.35049 (9)0.11348 (12)0.32500 (6)0.0269 (3)
H150.35600.06440.35630.032*
C160.36384 (11)0.56155 (13)0.44629 (6)0.0328 (3)
H16A0.34680.52750.48050.039*
H16B0.42570.57760.45060.039*
C170.31512 (9)0.67619 (12)0.43258 (5)0.0260 (3)
C180.31242 (9)0.88903 (12)0.46004 (5)0.0253 (3)
C190.36564 (11)0.97533 (13)0.48553 (6)0.0340 (3)
H190.41760.95200.50500.041*
C200.34301 (13)1.09500 (14)0.48259 (7)0.0426 (4)
H200.37951.15340.50010.051*
C210.26751 (13)1.12977 (14)0.45431 (7)0.0441 (4)
H210.25211.21180.45220.053*
C220.21490 (12)1.04423 (14)0.42929 (7)0.0413 (4)
H220.16281.06800.41020.050*
C230.23653 (10)0.92380 (14)0.43150 (6)0.0326 (3)
H230.20000.86590.41370.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0626 (3)0.0424 (3)0.0857 (4)0.0196 (2)−0.0237 (3)−0.0402 (3)
S10.02955 (18)0.02184 (18)0.0311 (2)0.00325 (13)−0.00802 (14)−0.00773 (13)
O10.0408 (6)0.0215 (5)0.0433 (6)0.0016 (4)0.0128 (5)−0.0058 (4)
O20.0428 (6)0.0307 (6)0.0301 (6)0.0088 (5)−0.0134 (5)−0.0077 (4)
N10.0330 (6)0.0258 (6)0.0359 (7)0.0051 (5)−0.0098 (5)−0.0085 (5)
N20.0341 (6)0.0230 (6)0.0303 (6)0.0038 (5)−0.0086 (5)−0.0072 (5)
N30.0261 (5)0.0176 (5)0.0233 (6)−0.0010 (4)−0.0026 (4)−0.0039 (4)
N40.0307 (6)0.0210 (6)0.0242 (6)0.0047 (4)−0.0045 (5)−0.0031 (4)
C10.0375 (9)0.0215 (7)0.0267 (9)0.0059 (6)0.0009 (7)−0.0028 (6)
C20.0271 (8)0.0300 (8)0.0598 (12)0.0046 (6)−0.0020 (8)−0.0135 (8)
C30.0313 (9)0.0409 (10)0.0618 (13)0.0121 (8)−0.0047 (9)−0.0187 (9)
C40.0446 (9)0.0289 (9)0.0373 (10)0.0125 (7)−0.0117 (8)−0.0140 (7)
C50.0467 (10)0.0269 (8)0.0496 (10)−0.0044 (7)0.0051 (8)−0.0071 (7)
C60.0394 (9)0.0290 (8)0.0482 (10)0.0002 (7)0.0137 (8)−0.0044 (7)
C1A0.0375 (9)0.0215 (7)0.0267 (9)0.0059 (6)0.0009 (7)−0.0028 (6)
C2A0.0271 (8)0.0300 (8)0.0598 (12)0.0046 (6)−0.0020 (8)−0.0135 (8)
C3A0.0313 (9)0.0409 (10)0.0618 (13)0.0121 (8)−0.0047 (9)−0.0187 (9)
C4A0.0446 (9)0.0289 (9)0.0373 (10)0.0125 (7)−0.0117 (8)−0.0140 (7)
C5A0.0467 (10)0.0269 (8)0.0496 (10)−0.0044 (7)0.0051 (8)−0.0071 (7)
C6A0.0394 (9)0.0290 (8)0.0482 (10)0.0002 (7)0.0137 (8)−0.0044 (7)
C70.0275 (7)0.0239 (7)0.0380 (8)0.0010 (5)−0.0008 (6)−0.0060 (6)
C80.0264 (6)0.0218 (7)0.0294 (7)0.0005 (5)−0.0028 (5)−0.0029 (5)
C90.0275 (6)0.0187 (6)0.0245 (7)−0.0005 (5)−0.0022 (5)−0.0038 (5)
C100.0256 (6)0.0208 (6)0.0210 (6)−0.0012 (5)0.0006 (5)−0.0057 (5)
C110.0475 (9)0.0235 (7)0.0265 (7)−0.0070 (6)−0.0006 (6)−0.0020 (6)
C120.0575 (10)0.0342 (8)0.0227 (7)−0.0004 (7)−0.0044 (7)0.0004 (6)
C130.0389 (8)0.0392 (8)0.0253 (7)0.0004 (6)−0.0047 (6)−0.0114 (6)
C140.0362 (8)0.0295 (7)0.0350 (8)−0.0081 (6)−0.0015 (6)−0.0098 (6)
C150.0313 (7)0.0239 (7)0.0251 (7)−0.0050 (5)0.0006 (6)−0.0026 (5)
C160.0482 (9)0.0246 (7)0.0237 (7)0.0112 (6)−0.0077 (6)−0.0076 (5)
C170.0324 (7)0.0235 (7)0.0216 (6)0.0036 (5)−0.0003 (5)−0.0029 (5)
C180.0346 (7)0.0204 (6)0.0214 (6)0.0029 (5)0.0053 (5)−0.0020 (5)
C190.0411 (8)0.0271 (8)0.0341 (8)−0.0014 (6)0.0042 (7)−0.0052 (6)
C200.0661 (11)0.0245 (8)0.0388 (9)−0.0061 (7)0.0130 (8)−0.0062 (7)
C210.0768 (13)0.0228 (8)0.0344 (9)0.0115 (8)0.0142 (8)0.0005 (6)
C220.0579 (10)0.0332 (9)0.0328 (8)0.0173 (7)0.0041 (8)0.0045 (7)
C230.0418 (8)0.0277 (7)0.0279 (7)0.0078 (6)0.0004 (6)−0.0007 (6)
Geometric parameters (Å, º) top
Cl1—C4A1.741 (11)C4A—C5A1.3900
Cl1—C41.7452 (16)C5A—C6A1.3900
S1—C91.7434 (14)C5A—H5A0.9500
S1—C161.8089 (14)C6A—H6A0.9500
O1—C11.3738 (17)C7—C81.4861 (19)
O1—C1A1.402 (11)C7—H7A0.9900
O1—C71.4277 (18)C7—H7B0.9900
O2—C171.2257 (17)C10—C111.3822 (19)
N1—C81.3065 (18)C10—C151.3843 (18)
N1—N21.3920 (16)C11—C121.392 (2)
N2—C91.3092 (17)C11—H110.9500
N3—C81.3703 (17)C12—C131.376 (2)
N3—C91.3724 (16)C12—H120.9500
N3—C101.4405 (16)C13—C141.383 (2)
N4—C171.3477 (17)C13—H130.9500
N4—C181.4189 (17)C14—C151.3858 (19)
N4—H40.9098C14—H140.9500
C1—C21.376 (2)C15—H150.9500
C1—C61.386 (2)C16—C171.5184 (19)
C2—C31.389 (2)C16—H16A0.9900
C2—H20.9500C16—H16B0.9900
C3—C41.378 (3)C18—C231.392 (2)
C3—H30.9500C18—C191.394 (2)
C4—C51.372 (3)C19—C201.386 (2)
C5—C61.383 (2)C19—H190.9500
C5—H50.9500C20—C211.384 (3)
C6—H60.9500C20—H200.9500
C1A—C2A1.3900C21—C221.378 (3)
C1A—C6A1.3900C21—H210.9500
C2A—C3A1.3900C22—C231.390 (2)
C2A—H2A0.9500C22—H220.9500
C3A—C4A1.3900C23—H230.9500
C3A—H3A0.9500
C9—S1—C1697.21 (6)H7A—C7—H7B108.5
C1—O1—C7116.88 (12)N1—C8—N3110.29 (12)
C1A—O1—C7118.7 (10)N1—C8—C7125.05 (13)
C8—N1—N2107.88 (11)N3—C8—C7124.65 (12)
C9—N2—N1106.56 (11)N2—C9—N3110.93 (12)
C8—N3—C9104.34 (11)N2—C9—S1126.94 (10)
C8—N3—C10127.37 (11)N3—C9—S1122.12 (10)
C9—N3—C10128.26 (11)C11—C10—C15121.26 (12)
C17—N4—C18127.18 (12)C11—C10—N3119.45 (12)
C17—N4—H4116.6C15—C10—N3119.29 (12)
C18—N4—H4116.1C10—C11—C12118.87 (13)
O1—C1—C2123.47 (16)C10—C11—H11120.6
O1—C1—C6115.96 (15)C12—C11—H11120.6
C2—C1—C6120.54 (14)C13—C12—C11120.47 (14)
C1—C2—C3119.60 (17)C13—C12—H12119.8
C1—C2—H2120.2C11—C12—H12119.8
C3—C2—H2120.2C12—C13—C14119.96 (14)
C4—C3—C2119.34 (16)C12—C13—H13120.0
C4—C3—H3120.3C14—C13—H13120.0
C2—C3—H3120.3C13—C14—C15120.45 (14)
C5—C4—C3121.28 (15)C13—C14—H14119.8
C5—C4—Cl1118.89 (15)C15—C14—H14119.8
C3—C4—Cl1119.78 (14)C10—C15—C14118.97 (13)
C4—C5—C6119.43 (16)C10—C15—H15120.5
C4—C5—H5120.3C14—C15—H15120.5
C6—C5—H5120.3C17—C16—S1107.17 (10)
C5—C6—C1119.73 (16)C17—C16—H16A110.3
C5—C6—H6120.1S1—C16—H16A110.3
C1—C6—H6120.1C17—C16—H16B110.3
C2A—C1A—C6A120.0S1—C16—H16B110.3
C2A—C1A—O1120.0 (14)H16A—C16—H16B108.5
C6A—C1A—O1118.4 (14)O2—C17—N4125.02 (12)
C1A—C2A—C3A120.0O2—C17—C16121.46 (12)
C1A—C2A—H2A120.0N4—C17—C16113.51 (12)
C3A—C2A—H2A120.0C23—C18—C19119.62 (13)
C2A—C3A—C4A120.0C23—C18—N4123.51 (13)
C2A—C3A—H3A120.0C19—C18—N4116.87 (13)
C4A—C3A—H3A120.0C20—C19—C18120.19 (15)
C3A—C4A—C5A120.0C20—C19—H19119.9
C3A—C4A—Cl1107.1 (13)C18—C19—H19119.9
C5A—C4A—Cl1132.6 (13)C21—C20—C19120.30 (16)
C6A—C5A—C4A120.0C21—C20—H20119.9
C6A—C5A—H5A120.0C19—C20—H20119.9
C4A—C5A—H5A120.0C22—C21—C20119.39 (15)
C5A—C6A—C1A120.0C22—C21—H21120.3
C5A—C6A—H6A120.0C20—C21—H21120.3
C1A—C6A—H6A120.0C21—C22—C23121.27 (16)
O1—C7—C8107.16 (12)C21—C22—H22119.4
O1—C7—H7A110.3C23—C22—H22119.4
C8—C7—H7A110.3C22—C23—C18119.23 (15)
O1—C7—H7B110.3C22—C23—H23120.4
C8—C7—H7B110.3C18—C23—H23120.4
C8—N1—N2—C9−0.32 (16)N1—N2—C9—N30.68 (16)
C7—O1—C1—C228.4 (2)N1—N2—C9—S1−177.94 (11)
C7—O1—C1—C6−153.50 (14)C8—N3—C9—N2−0.75 (15)
O1—C1—C2—C3175.06 (16)C10—N3—C9—N2177.55 (12)
C6—C1—C2—C3−3.0 (3)C8—N3—C9—S1177.94 (10)
C1—C2—C3—C41.2 (3)C10—N3—C9—S1−3.76 (19)
C2—C3—C4—C51.0 (3)C16—S1—C9—N22.70 (15)
C2—C3—C4—Cl1−176.55 (15)C16—S1—C9—N3−175.77 (12)
C3—C4—C5—C6−1.3 (3)C8—N3—C10—C11−117.80 (16)
Cl1—C4—C5—C6176.23 (14)C9—N3—C10—C1164.27 (19)
C4—C5—C6—C1−0.5 (3)C8—N3—C10—C1561.47 (18)
O1—C1—C6—C5−175.53 (16)C9—N3—C10—C15−116.46 (15)
C2—C1—C6—C52.7 (3)C15—C10—C11—C120.3 (2)
C7—O1—C1A—C2A−40.3 (19)N3—C10—C11—C12179.60 (13)
C7—O1—C1A—C6A154.0 (11)C10—C11—C12—C13−1.2 (2)
C6A—C1A—C2A—C3A0.0C11—C12—C13—C140.8 (2)
O1—C1A—C2A—C3A−166 (2)C12—C13—C14—C150.5 (2)
C1A—C2A—C3A—C4A0.0C11—C10—C15—C140.9 (2)
C2A—C3A—C4A—C5A0.0N3—C10—C15—C14−178.32 (13)
C2A—C3A—C4A—Cl1175 (2)C13—C14—C15—C10−1.4 (2)
C3A—C4A—C5A—C6A0.0C9—S1—C16—C17162.90 (11)
Cl1—C4A—C5A—C6A−173 (3)C18—N4—C17—O2−5.4 (2)
C4A—C5A—C6A—C1A0.0C18—N4—C17—C16173.55 (13)
C2A—C1A—C6A—C5A0.0S1—C16—C17—O210.32 (18)
O1—C1A—C6A—C5A166 (2)S1—C16—C17—N4−168.65 (10)
C1—O1—C7—C8169.54 (13)C17—N4—C18—C2322.5 (2)
C1A—O1—C7—C8−175.2 (13)C17—N4—C18—C19−157.94 (14)
N2—N1—C8—N3−0.15 (16)C23—C18—C19—C200.2 (2)
N2—N1—C8—C7178.55 (13)N4—C18—C19—C20−179.40 (14)
C9—N3—C8—N10.54 (16)C18—C19—C20—C21−0.1 (2)
C10—N3—C8—N1−177.78 (13)C19—C20—C21—C220.3 (3)
C9—N3—C8—C7−178.17 (13)C20—C21—C22—C23−0.6 (3)
C10—N3—C8—C73.5 (2)C21—C22—C23—C180.7 (2)
O1—C7—C8—N1103.81 (16)C19—C18—C23—C22−0.5 (2)
O1—C7—C8—N3−77.67 (17)N4—C18—C23—C22179.06 (14)
Hydrogen-bond geometry (Å, º) top
Cg3 and Cg4 are the centroids of the C10–C15 and C18–C23 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N4—H4···N1i0.912.022.9230 (17)174
C7—H7B···O2ii0.992.493.3518 (18)146
C3—H3···Cg3iii0.952.923.867 (2)174
C15—H15···Cg4iv0.952.863.6871 (16)146
C16—H16A···Cg4v0.992.803.6488 (18)144
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, y−1/2, z; (iii) −x, −y−1, −z; (iv) x, y−1, z; (v) −x+1/2, −y+3/2, −z+1.
Hydrogen-bond geometry (Å, º) top
Cg3 and Cg4 are the centroids of the C10–C15 and C18–C23 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N4—H4···N1i0.912.022.9230 (17)174
C7—H7B···O2ii0.992.493.3518 (18)146
C3—H3···Cg3iii0.952.923.867 (2)174
C15—H15···Cg4iv0.952.863.6871 (16)146
C16—H16A···Cg4v0.992.803.6488 (18)144
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, y−1/2, z; (iii) −x, −y−1, −z; (iv) x, y−1, z; (v) −x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formulaC23H19ClN4O2S
Mr450.93
Crystal system, space groupMonoclinic, C2/c
Temperature (K)150
a, b, c (Å)15.7940 (12), 11.1864 (8), 24.8212 (18)
β (°) 95.128 (1)
V (Å3)4367.8 (6)
Z8
Radiation typeMo Kα
µ (mm−1)0.30
Crystal size (mm)0.24 × 0.20 × 0.11
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2016)
Tmin, Tmax0.86, 0.97
No. of measured, independent and
observed [I > 2σ(I)] reflections		41579, 5886, 4471
Rint0.045
(sin θ/λ)max (Å−1)0.686
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.118, 1.06
No. of reflections5886
No. of parameters287
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.41, −0.21

Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), DIAMOND (Brandenburg & Putz, 2012), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

First citationBektaş, H., Karaali, N., Şahin, D., Demirbaş, A., Karaoglu, S. A., Şengül, A. & Demirbaş, N. (2010). Molecules, 15, 2427–2438.  PubMed Google Scholar
 First citationBrandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationJawad, A. H., Shneine, J. K., Ahmed, A. & Abdulrasool, M. M. (2012). Int. J. Re. Pharm. Chem. (IJRPC), 2, 1109–1123.  CAS Google Scholar
 First citationShaker, R. M. (2006). ARKIVOC, ix, 59–112.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSinghal, N., Sharma, P. K., Dudhe, R. & Kumar, N. (2011). J. Chem. Pharm. Res. 3, 126–133.  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 3| March 2016| x160453
doi:10.1107/S2414314616004533
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