(4Z)-1-[(E)-(4-Meth­oxy­benzyl­idene)amino]-2-phenyl-4-[(thio­phen-2-yl)­methyl­idene]-1H-imidazol-5(4H)-one

Singh, V.D.; Kamni; Subbulakshmi, K.N.; Narayana, B.; Sarojini, B.K.; Anthal, S.; Kant, R.

doi:10.1107/S2414314616005666

organic compounds

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ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160566

doi:10.1107/S2414314616005666

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(4Z)-1-[(E)-(4-Methoxybenzylidene)amino]-2-phenyl-4-[(thiophen-2-yl)methylidene]-1H-imidazol-5(4H)-one

Vikram D. Singh,^a Kamni,^a K. N. Subbulakshmi,^b B. Narayana,^b B. K. Sarojini,^c Sumati Anthal ^d and Rajni Kant ^d ^*

^aSchool of Physics, Shri Mata Vaishno Devi University, Katra 182 320, J&K, India, ^bDepartment of Chemistry, Mangalore University, Mangalagangothri 574 199, D.K., Mangalore, India, ^cDepartment of Industrial Chemistry, Mangalore University, Mangalagangothri 574 199, D.K., Mangalore, India, and ^dX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
^*Correspondence e-mail: rkant.ju@gmail.com

Edited by A. J. Lough, University of Toronto, Canada (Received 25 March 2016; accepted 5 April 2016; online 12 April 2016)

In the title compound, C₂₂H₁₇N₃O₂S, the imidazole ring forms dihedral angles of 9.2 (2), 10.9 (2) and 12.5 (2)° with the thiophene, phenyl and methoxy-substituted benzene rings, respectively. There are two intramolecular C—H⋯N hydrogen bonds forming S(5) and S(6) rings and one intramolecular C—H⋯O hydrogen bond forming an S(6) ring.

Keywords: crystal structure; imidazole; hydrogen bonding.

CCDC reference: 1472471

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Chemical scheme

Structure description

Compounds containing the imidazolone as well as the imine moiety exhibit pharmaceutical activities such as antimicrobial (Suthakaran et al., 2008 ; Patel et al., 2006 ), anti-oxidant (Suhasini et al., 2014 ), anticonvulsant (Mohamed et al., 2012 ), anthelmintic (Patel et al., 2010 ) antibacterial (Solankee et al., 2011 ) analgesic (Sridhar & Ramesh, 2001 ), anti-inflammatory (Viveka et al., 2015 ) and antitumor (Hodnett & Dunn, 1970 ). Apart from their biological activity, Schiff bases have assumed importance as ligands in coordination chemistry (Özkar et al. 2004 , Pouralimardan et al., 2007 ; Patti et al., 2009 ). Structural information on the title compound is useful in developing the coordination properties of Schiff bases and to investigate new ligands.

The molecular structure of the title compound is shown in Fig. 1. The bond lengths and angles have normal values and all aromatic rings are essentially planar. The imidazole ring forms dihedral angles of 9.2 (2), 10.9 (2) and 12.5 (2)° with the thiophene (S1/C1–C4), phenyl (C9–C14) and methoxy-substituted benzene (C16–C21) rings, respectively. The methoxy group is essentially planar with the benzene ring to which it is attached, with a C22—O2—C19—C18 torsion angle of −0.8 (4)°. There are two intramolecular C—H⋯N hydrogen bonds (Table 1), forming S(5) and S(6) rings, and one intramolecular C—H⋯O hydrogen bond forming an S(6) ring (Fig. 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯N1	0.93	2.46	2.792 (4)	101
C14—H14⋯N3	0.93	2.32	2.942 (4)	124
C15—H15⋯O1	0.93	2.21	2.867 (3)	127

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate weak intramolecular hydrogen bonds.

Synthesis and crystallization

A mixture of 3-hydrazinyl-3-oxo-1-(thiophen-2-yl)prop-1-en-2-yl]benzamide (0.01 mol) in 2-propanol (30 ml) with 4-methoxybenzaldehyde (0.01 mol) in presence of one to two drops of sulfuric acid were heated under reflux for 8 h. The reaction mixture was cooled to ambient temperature and poured on cold water. The solid mass obtained was collected by filtration and washed with cold water. It was crystallized at ambient temperature in the presence of air from a mixture of methanol and N,N-dimethylformamide(1:1 v/v) (m.p. 421 K).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₁₇N₃O₂S
M_r	387.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	20.6796 (18), 5.4004 (4), 17.2537 (16)
β (°)	104.299 (9)
V (Å³)	1867.2 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ )
T_min, T_max	0.769, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7300, 3663, 2215
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.136, 1.05
No. of reflections	3663
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1472471

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2414314616005666/lh4005sup1.cif

Supporting information file. DOI: 10.1107/S2414314616005666/lh4005Isup2.cml

checkCIF report

Comment top

Compounds containing the imidazolone as well as the imine moiety exhibit an important role in pharmaceutical activities, such as antimicrobial (Suthakaran et al., 2008; Patel et al., 2006), antioxidant (Suhasini et al., 2014), anticonvulsant (Mohamed et al., 2012), anthelmintic (Patel et al., 2010) antibacterial (Solankee et al., 2011) analgesic (Sridhar & Ramesh, 2001), anti-inflammatory (Viveka et al., 2015), and antitumor (Hodnett & Dunn, 1970). Apart from biological activity, Schiff bases have assumed importance as ligands in coordination chemistry (Özkar et al. 2004, Pouralimardan et al., 2007; Patti et al., 2009). Structural information of the title compound is useful in developing coordination properties of Schiff bases and to investigate new ligands.

The molecular structure of the title compound is shown in Fig. 1. The bond lengths (Allen et al. 1987) and bond angles in the title compound have normal values and all aromatic rings are essentially planar. The imidazole ring forms dihedral angles of 9.2 (2)°, 10.9 (2)° and 12.5 (2)° with the thiophene [S1/C1-C4] , phenyl [C9-C14] and methoxy-substituted benzene [C16-C21] rings, respectively. The methoxy group is essentially planar with the benzene ring to which it is attached with a C22-O2-C19-C18 torsion angle of -0.8 (4)°. There are two intramolecular C—H···N hydrogen bonds forming S(5) and S(6) rings and one intramolecular C—H···O hydrogen bond forming an S(6) ring (Fig. 1).

Experimental top

Structure description top

Compounds containing the imidazolone as well as the imine moiety exhibit pharmaceutical activities such as antimicrobial (Suthakaran et al., 2008; Patel et al., 2006), anti-oxidant (Suhasini et al., 2014), anticonvulsant (Mohamed et al., 2012), anthelmintic (Patel et al., 2010) antibacterial (Solankee et al., 2011) analgesic (Sridhar & Ramesh, 2001), anti-inflammatory (Viveka et al., 2015) and antitumor (Hodnett & Dunn, 1970). Apart from their biological activity, Schiff bases have assumed importance as ligands in coordination chemistry (Özkar et al. 2004, Pouralimardan et al., 2007; Patti et al., 2009). Structural information on the title compound is useful in developing the coordination properties of Schiff bases and to investigate new ligands.

The molecular structure of the title compound is shown in Fig. 1. The bond lengths and angles have normal values and all aromatic rings are essentially planar. The imidazole ring forms dihedral angles of 9.2 (2), 10.9 (2) and 12.5 (2)° with the thiophene (S1/C1–C4), phenyl (C9–C14) and methoxy-substituted benzene (C16–C21) rings, respectively. The methoxy group is essentially planar with the benzene ring to which it is attached, with a C22—O2—C19—C18 torsion angle of -0.8 (4)°. There are two intramolecular C—H···N hydrogen bonds (Table 1), forming S(5) and S(6) rings, and one intramolecular C—H···O hydrogen bond forming an S(6) ring (Fig. 1).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate weak intramolecular hydrogen bonds.

(4Z)-1-[(E)-(4-Methoxybenzylidene)amino]-2-phenyl-4-[(thiophen-2-yl)methylidene]-1H-imidazol-5(4H)-one top

Crystal data top

C₂₂H₁₇N₃O₂S	F(000) = 808
M_r = 387.45	D_x = 1.378 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1894 reflections
a = 20.6796 (18) Å	θ = 4.2–27.1°
b = 5.4004 (4) Å	µ = 0.20 mm⁻¹
c = 17.2537 (16) Å	T = 293 K
β = 104.299 (9)°	Rectangular, white
V = 1867.2 (3) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3663 independent reflections
Radiation source: fine-focus sealed tube	2215 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.9°
ω scans	h = −21→25
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −6→4
T_min = 0.769, T_max = 1.000	l = −21→15
7300 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0436P)² + 0.2269P] where P = (F_o² + 2F_c²)/3
3663 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₂H₁₇N₃O₂S	V = 1867.2 (3) Å³
M_r = 387.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.6796 (18) Å	µ = 0.20 mm⁻¹
b = 5.4004 (4) Å	T = 293 K
c = 17.2537 (16) Å	0.30 × 0.20 × 0.20 mm
β = 104.299 (9)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3663 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	2215 reflections with I > 2σ(I)
T_min = 0.769, T_max = 1.000	R_int = 0.028
7300 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
3663 reflections	Δρ_min = −0.23 e Å⁻³
255 parameters

Special details top

Experimental. Absorption correction: CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
S1	0.44505 (4)	0.95712 (13)	0.26907 (4)	0.0566 (3)
N1	0.33090 (10)	0.8287 (4)	0.12524 (13)	0.0476 (6)
C9	0.28224 (12)	1.0201 (5)	−0.00327 (15)	0.0435 (6)
N2	0.23366 (10)	0.6575 (4)	0.05940 (13)	0.0469 (5)
O1	0.22389 (9)	0.3399 (4)	0.14907 (11)	0.0633 (6)
C7	0.25357 (14)	0.5141 (5)	0.12958 (16)	0.0498 (7)
C8	0.28221 (12)	0.8389 (5)	0.06065 (15)	0.0444 (6)
N3	0.17324 (11)	0.6492 (4)	0.00114 (13)	0.0518 (6)
C10	0.33009 (13)	1.2060 (5)	0.01438 (17)	0.0508 (7)
H10	0.3591	1.2132	0.0650	0.061*
C5	0.35065 (13)	0.5749 (5)	0.24616 (16)	0.0499 (7)
H5	0.3359	0.4344	0.2678	0.060*
C14	0.23988 (13)	1.0125 (5)	−0.07990 (17)	0.0539 (7)
H14	0.2079	0.8885	−0.0930	0.065*
O2	−0.11004 (10)	0.3630 (4)	−0.22410 (13)	0.0745 (6)
C4	0.40723 (13)	0.6972 (5)	0.29599 (15)	0.0473 (7)
C1	0.50041 (14)	0.9677 (6)	0.36046 (17)	0.0613 (8)
H1	0.5338	1.0866	0.3749	0.074*
C13	0.24499 (15)	1.1877 (5)	−0.13666 (17)	0.0595 (8)
H13	0.2164	1.1812	−0.1875	0.071*
C12	0.29240 (15)	1.3713 (5)	−0.11775 (18)	0.0600 (8)
H12	0.2957	1.4896	−0.1558	0.072*
C2	0.49050 (14)	0.7853 (6)	0.40935 (18)	0.0618 (8)
H2	0.5161	0.7651	0.4614	0.074*
C6	0.31598 (13)	0.6373 (5)	0.17177 (16)	0.0479 (7)
C16	0.07441 (14)	0.4331 (5)	−0.06258 (16)	0.0527 (7)
C15	0.13843 (14)	0.4562 (5)	−0.00441 (17)	0.0601 (8)
H15	0.1540	0.3241	0.0297	0.072*
C19	−0.04988 (14)	0.3744 (5)	−0.16912 (17)	0.0543 (7)
C21	0.05040 (15)	0.6050 (5)	−0.12224 (18)	0.0634 (8)
H21	0.0762	0.7426	−0.1268	0.076*
C3	0.43762 (14)	0.6291 (5)	0.37355 (16)	0.0555 (7)
H3	0.4243	0.4939	0.3992	0.067*
C11	0.33506 (14)	1.3800 (5)	−0.04245 (18)	0.0580 (8)
H11	0.3673	1.5035	−0.0299	0.070*
C17	0.03512 (17)	0.2308 (6)	−0.0599 (2)	0.0823 (11)
H17	0.0507	0.1090	−0.0217	0.099*
C18	−0.02719 (16)	0.2015 (6)	−0.1122 (2)	0.0762 (10)
H18	−0.0532	0.0639	−0.1081	0.091*
C20	−0.01077 (15)	0.5760 (6)	−0.17477 (19)	0.0674 (9)
H20	−0.0259	0.6935	−0.2145	0.081*
C22	−0.15119 (16)	0.1525 (6)	−0.2217 (2)	0.0901 (12)
H22A	−0.1300	0.0068	−0.2357	0.135*
H22B	−0.1937	0.1750	−0.2590	0.135*
H22C	−0.1576	0.1342	−0.1687	0.135*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0543 (5)	0.0598 (5)	0.0512 (5)	−0.0039 (4)	0.0044 (4)	0.0050 (3)
N1	0.0426 (13)	0.0533 (13)	0.0432 (13)	−0.0023 (10)	0.0038 (11)	0.0027 (10)
C9	0.0389 (15)	0.0493 (15)	0.0421 (15)	0.0057 (12)	0.0096 (12)	0.0014 (12)
N2	0.0385 (12)	0.0565 (13)	0.0431 (13)	−0.0050 (11)	0.0051 (10)	−0.0003 (10)
O1	0.0606 (13)	0.0725 (13)	0.0539 (13)	−0.0183 (11)	0.0089 (11)	0.0084 (10)
C7	0.0466 (16)	0.0599 (18)	0.0420 (16)	−0.0003 (14)	0.0092 (13)	−0.0004 (13)
C8	0.0377 (14)	0.0510 (16)	0.0440 (16)	−0.0024 (13)	0.0090 (13)	−0.0023 (12)
N3	0.0378 (13)	0.0688 (15)	0.0450 (13)	−0.0054 (12)	0.0032 (11)	−0.0018 (11)
C10	0.0443 (16)	0.0549 (17)	0.0515 (17)	−0.0014 (13)	0.0089 (14)	−0.0028 (13)
C5	0.0461 (16)	0.0572 (16)	0.0457 (16)	0.0024 (13)	0.0103 (13)	0.0079 (13)
C14	0.0468 (16)	0.0619 (18)	0.0491 (17)	−0.0001 (14)	0.0042 (14)	0.0011 (14)
O2	0.0502 (13)	0.0910 (15)	0.0701 (15)	−0.0045 (12)	−0.0083 (11)	−0.0081 (12)
C4	0.0437 (15)	0.0558 (16)	0.0413 (15)	0.0073 (13)	0.0087 (13)	0.0036 (12)
C1	0.0500 (18)	0.0685 (19)	0.0581 (19)	−0.0053 (15)	−0.0002 (15)	−0.0074 (16)
C13	0.0559 (19)	0.070 (2)	0.0478 (17)	0.0097 (16)	0.0038 (15)	0.0091 (15)
C12	0.063 (2)	0.0571 (18)	0.063 (2)	0.0128 (16)	0.0204 (17)	0.0121 (15)
C2	0.0523 (18)	0.079 (2)	0.0469 (17)	0.0021 (16)	−0.0008 (15)	0.0030 (16)
C6	0.0422 (15)	0.0557 (16)	0.0431 (15)	−0.0012 (13)	0.0055 (13)	0.0026 (13)
C16	0.0495 (17)	0.0588 (17)	0.0459 (16)	−0.0063 (15)	0.0045 (14)	−0.0035 (14)
C15	0.0549 (18)	0.0609 (18)	0.0566 (19)	−0.0094 (16)	−0.0008 (15)	−0.0005 (15)
C19	0.0455 (16)	0.0651 (19)	0.0477 (17)	−0.0018 (15)	0.0029 (14)	−0.0114 (15)
C21	0.0567 (19)	0.0653 (19)	0.063 (2)	−0.0126 (16)	0.0040 (16)	0.0053 (16)
C3	0.0524 (17)	0.0639 (18)	0.0459 (17)	0.0007 (15)	0.0039 (14)	0.0076 (14)
C11	0.0522 (17)	0.0547 (17)	0.067 (2)	0.0003 (14)	0.0147 (16)	0.0052 (16)
C17	0.082 (2)	0.080 (2)	0.066 (2)	−0.027 (2)	−0.0183 (19)	0.0186 (18)
C18	0.071 (2)	0.080 (2)	0.064 (2)	−0.0310 (19)	−0.0078 (18)	0.0067 (18)
C20	0.063 (2)	0.069 (2)	0.061 (2)	−0.0026 (17)	−0.0006 (17)	0.0091 (16)
C22	0.054 (2)	0.098 (3)	0.105 (3)	−0.015 (2)	−0.005 (2)	−0.022 (2)

Geometric parameters (Å, º) top

S1—C1	1.705 (3)	C1—H1	0.9300
S1—C4	1.725 (3)	C13—C12	1.376 (4)
N1—C8	1.306 (3)	C13—H13	0.9300
N1—C6	1.389 (3)	C12—C11	1.379 (4)
C9—C10	1.390 (3)	C12—H12	0.9300
C9—C14	1.395 (3)	C2—C3	1.398 (4)
C9—C8	1.475 (3)	C2—H2	0.9300
N2—N3	1.398 (3)	C16—C17	1.369 (4)
N2—C8	1.399 (3)	C16—C21	1.384 (4)
N2—C7	1.410 (3)	C16—C15	1.456 (4)
O1—C7	1.215 (3)	C15—H15	0.9300
C7—C6	1.475 (3)	C19—C18	1.353 (4)
N3—C15	1.257 (3)	C19—C20	1.374 (4)
C10—C11	1.380 (4)	C21—C20	1.371 (4)
C10—H10	0.9300	C21—H21	0.9300
C5—C6	1.349 (3)	C3—H3	0.9300
C5—C4	1.431 (3)	C11—H11	0.9300
C5—H5	0.9300	C17—C18	1.388 (4)
C14—C13	1.384 (4)	C17—H17	0.9300
C14—H14	0.9300	C18—H18	0.9300
O2—C19	1.367 (3)	C20—H20	0.9300
O2—C22	1.426 (3)	C22—H22A	0.9600
C4—C3	1.380 (3)	C22—H22B	0.9600
C1—C2	1.345 (4)	C22—H22C	0.9600

C1—S1—C4	91.37 (14)	C1—C2—H2	123.6
C8—N1—C6	106.9 (2)	C3—C2—H2	123.6
C10—C9—C14	118.4 (2)	C5—C6—N1	126.4 (2)
C10—C9—C8	116.6 (2)	C5—C6—C7	123.5 (3)
C14—C9—C8	125.0 (2)	N1—C6—C7	110.0 (2)
N3—N2—C8	123.0 (2)	C17—C16—C21	117.0 (3)
N3—N2—C7	128.3 (2)	C17—C16—C15	119.4 (3)
C8—N2—C7	108.4 (2)	C21—C16—C15	123.6 (3)
O1—C7—N2	127.0 (3)	N3—C15—C16	122.0 (3)
O1—C7—C6	130.8 (3)	N3—C15—H15	119.0
N2—C7—C6	102.1 (2)	C16—C15—H15	119.0
N1—C8—N2	112.5 (2)	C18—C19—O2	124.4 (3)
N1—C8—C9	121.6 (2)	C18—C19—C20	119.6 (3)
N2—C8—C9	125.9 (2)	O2—C19—C20	115.9 (3)
C15—N3—N2	118.3 (2)	C20—C21—C16	121.2 (3)
C11—C10—C9	120.7 (3)	C20—C21—H21	119.4
C11—C10—H10	119.7	C16—C21—H21	119.4
C9—C10—H10	119.7	C4—C3—C2	112.7 (3)
C6—C5—C4	128.3 (3)	C4—C3—H3	123.6
C6—C5—H5	115.8	C2—C3—H3	123.6
C4—C5—H5	115.8	C12—C11—C10	120.2 (3)
C13—C14—C9	120.7 (3)	C12—C11—H11	119.9
C13—C14—H14	119.6	C10—C11—H11	119.9
C9—C14—H14	119.6	C16—C17—C18	122.2 (3)
C19—O2—C22	117.6 (2)	C16—C17—H17	118.9
C3—C4—C5	124.6 (3)	C18—C17—H17	118.9
C3—C4—S1	110.5 (2)	C19—C18—C17	119.6 (3)
C5—C4—S1	124.9 (2)	C19—C18—H18	120.2
C2—C1—S1	112.6 (2)	C17—C18—H18	120.2
C2—C1—H1	123.7	C21—C20—C19	120.4 (3)
S1—C1—H1	123.7	C21—C20—H20	119.8
C12—C13—C14	119.9 (3)	C19—C20—H20	119.8
C12—C13—H13	120.0	O2—C22—H22A	109.5
C14—C13—H13	120.0	O2—C22—H22B	109.5
C13—C12—C11	120.0 (3)	H22A—C22—H22B	109.5
C13—C12—H12	120.0	O2—C22—H22C	109.5
C11—C12—H12	120.0	H22A—C22—H22C	109.5
C1—C2—C3	112.9 (3)	H22B—C22—H22C	109.5

N3—N2—C7—O1	7.1 (4)	C4—C5—C6—N1	4.4 (5)
C8—N2—C7—O1	−180.0 (3)	C4—C5—C6—C7	−172.6 (2)
N3—N2—C7—C6	−170.7 (2)	C8—N1—C6—C5	−174.8 (3)
C8—N2—C7—C6	2.3 (3)	C8—N1—C6—C7	2.5 (3)
C6—N1—C8—N2	−1.0 (3)	O1—C7—C6—C5	−3.1 (5)
C6—N1—C8—C9	−179.0 (2)	N2—C7—C6—C5	174.5 (2)
N3—N2—C8—N1	172.4 (2)	O1—C7—C6—N1	179.5 (3)
C7—N2—C8—N1	−1.0 (3)	N2—C7—C6—N1	−2.9 (3)
N3—N2—C8—C9	−9.6 (4)	N2—N3—C15—C16	179.1 (2)
C7—N2—C8—C9	177.0 (2)	C17—C16—C15—N3	−172.5 (3)
C10—C9—C8—N1	−10.9 (4)	C21—C16—C15—N3	8.1 (5)
C14—C9—C8—N1	166.7 (2)	C22—O2—C19—C18	−0.8 (4)
C10—C9—C8—N2	171.4 (2)	C22—O2—C19—C20	178.1 (3)
C14—C9—C8—N2	−11.1 (4)	C17—C16—C21—C20	1.6 (5)
C8—N2—N3—C15	166.7 (2)	C15—C16—C21—C20	−179.0 (3)
C7—N2—N3—C15	−21.3 (4)	C5—C4—C3—C2	−178.0 (2)
C14—C9—C10—C11	0.6 (4)	S1—C4—C3—C2	−0.3 (3)
C8—C9—C10—C11	178.3 (2)	C1—C2—C3—C4	−0.1 (4)
C10—C9—C14—C13	−0.7 (4)	C13—C12—C11—C10	−0.5 (4)
C8—C9—C14—C13	−178.2 (2)	C9—C10—C11—C12	0.0 (4)
C6—C5—C4—C3	176.1 (3)	C21—C16—C17—C18	−2.4 (5)
C6—C5—C4—S1	−1.3 (4)	C15—C16—C17—C18	178.1 (3)
C1—S1—C4—C3	0.5 (2)	O2—C19—C18—C17	179.3 (3)
C1—S1—C4—C5	178.2 (2)	C20—C19—C18—C17	0.4 (5)
C4—S1—C1—C2	−0.6 (2)	C16—C17—C18—C19	1.5 (6)
C9—C14—C13—C12	0.2 (4)	C16—C21—C20—C19	0.2 (5)
C14—C13—C12—C11	0.4 (4)	C18—C19—C20—C21	−1.2 (5)
S1—C1—C2—C3	0.5 (3)	O2—C19—C20—C21	179.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···N1	0.93	2.46	2.792 (4)	101
C14—H14···N3	0.93	2.32	2.942 (4)	124
C15—H15···O1	0.93	2.21	2.867 (3)	127

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···N1	0.93	2.46	2.792 (4)	101
C14—H14···N3	0.93	2.32	2.942 (4)	124
C15—H15···O1	0.93	2.21	2.867 (3)	127

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇N₃O₂S
M_r	387.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	20.6796 (18), 5.4004 (4), 17.2537 (16)
β (°)	104.299 (9)
V (Å³)	1867.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.769, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7300, 3663, 2215
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.136, 1.05
No. of reflections	3663
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).

Acknowledgements

RK acknowledges the Indian Council of Medical Research, New Delhi, for Financial Support under Research Project No. BIC/12 (14)/2012. SNK acknowledges the Department of Chemistry, Shri MadhwaVadiraja Institute of Technology, Bantakal (VTU Belgam), for providing research facilities.

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