5-(4-Meth­oxy­phen­yl)-3-phenyl­iso­thia­zole

Chakravarthy, A.S.J.; Manushree, V.; Yashwanth, H.J.; Sreenatha, N.R.

doi:10.1107/S2414314626010151

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 10| October 2026| x261015

https://doi.org/10.1107/S2414314626010151

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5-(4-Methoxyphenyl)-3-phenylisothiazole

A. S. Jeevan Chakravarthy,^a ^* V. Manushree,^b H. J. Yashwanth ^c and N. R. Sreenatha ^d ^*

^aDepartment of Chemistry, BMS Institute of Technology & Management, Autonomous under Visvesvaraya Technological University, Avalahalli, Yelahanka, Bengaluru 560064, Karnataka, India, ^bDepartment of Microbiology, Krupanidhi Degree College, Bangalore, Karnataka 560035, India, ^cDepartment of Physics, Nitte Meenakshi Institute of Technology, Nitte (Deemed to be University), Bengaluru 560 064, Karnataka, India, and ^dResearch Center, Department of Physics, Government Engineering College, Bedarapura, Chamarajanagara 571313, Karnataka, India
^*Correspondence e-mail: [email protected], [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 26 September 2026; accepted 29 September 2026; online 2 October 2026)

In the title compound, C₁₆H₁₃NOS, the dihedral angles between the central isothiazole ring and pendant phenyl and p-methoxyphenyl rings are 41.57 (15) and 4.63 (13)°, respectively. In the extended structure, weak C—H⋯π interactions may help to consolidate the packing.

Keywords: isothiazole; dihedral angle; crystal structure.

CCDC reference: 2577952

Structure description

The title compound, C₁₆H₁₃NOS (2), crystallizes with one molecule in the asymmetric unit (Fig. 1) in space group P2₁. The dihdral angles between the central C1–C3/N1/S1 isothiazole ring and pendant C4–C9 phenyl and C10–C15 p-methoxybenzene rings are 41.57 (15) and 4.63 (13)°, respectively. This suggests the possibility of enhanced conjugation between the C1 and C10 rings, but the C1—C10 and C3—C4 bond lengths of 1.471 (3) and 1.474 (4) Å, respectively, are almost identical. A short intramolecular C11—H11⋯S1 contact (Table 1) occurs. Otherwise, the bond lengths and angles of 2 are within the ranges reported for related structures in the literature (Akkurt et al., 2015 ; Sreenatha et al., 2018 , 2021 ; Sukhonosova et al., 2016 ; Meundaeng et al., 2019 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C3/N1/S1, C4–C9 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯S1	0.93	2.73	3.137 (3)	107
C8—H8⋯Cg2ⁱ	0.93	2.82	3.503 (4)	132
C12—H12⋯Cg1ⁱⁱ	0.93	2.88	3.542 (4)	129
C15—H15⋯Cg3ⁱⁱⁱ	0.93	2.92	3.688 (3)	140
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Figure 1
The molecular structure of 2 with displacement ellipsoids drawn at the 50% probability level. The short C—H⋯S contact is shown as a dashed line.

In the extended structure of 2, weak C—H⋯π interactions (Table 1) may help to establish the packing (Fig. 2), with each ring accepting one such interaction.

Figure 2
The packing of 2 viewed along the crystallographic a axis.

Synthesis and crystallization

The title compound was prepared by the literature method (Fig. 3) (Zhang et al. 2021 ) and 0.5 g of it was dissolved in 5 ml of N,N-dimethlformamide and was allowed to undergo slow evaporation to form colourless blocks of 2.

Figure 3
Synthesis scheme of the title compound.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NOS
M_r	267.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	6.0239 (2), 7.4924 (2), 14.7003 (5)
β (°)	92.779 (1)
V (Å³)	662.70 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.23
Crystal size (mm)	0.31 × 0.28 × 0.23

Data collection
Diffractometer	Bruker SMART APEX
No. of measured, independent and observed [I > 2σ(I)] reflections	40942, 4059, 3351
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.130, 1.01
No. of reflections	4059
No. of parameters	173
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.23
Absolute structure	Flack x determined using 1295 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.13 (5)
Computer programs: APEX and SAINT (Bruker, 2012 ), SHELXT2014/4 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ) and PLATON(Spek, 2009 ).

Structural data

CCDC reference: 2577952

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314626010151/hb4573sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626010151/hb4573Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626010151/hb4573Isup3.cml

checkCIF report

Computing details top

5-(4-Methoxyphenyl)-3-phenylisothiazole top

Crystal data top

C₁₆H₁₃NOS	F(000) = 280
M_r = 267.33	D_x = 1.340 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 6.0239 (2) Å	Cell parameters from 40942 reflections
b = 7.4924 (2) Å	θ = 3.1–30.5°
c = 14.7003 (5) Å	µ = 0.23 mm⁻¹
β = 92.779 (1)°	T = 298 K
V = 662.70 (4) Å³	Block, colourless
Z = 2	0.31 × 0.28 × 0.23 mm

Data collection top

Bruker SMART APEX diffractometer	R_int = 0.103
Radiation source: graphite	θ_max = 30.5°, θ_min = 3.1°
40942 measured reflections	h = −8→8
4059 independent reflections	k = −10→10
3351 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.047	w = 1/[σ²(F_o²) + (0.0801P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.130	(Δ/σ)_max = 0.001
S = 1.01	Δρ_max = 0.34 e Å⁻³
4059 reflections	Δρ_min = −0.23 e Å⁻³
173 parameters	Absolute structure: Flack x determined using 1295 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.13 (5)

Special details top

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. Hydrogen atoms were placed in the calculated positions and refined as riding: C—H = 0.93Å with U_iso(H) = 1.2U_eq(C) for aromatic H atoms and C—H = 0.96 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.4874 (4)	0.6019 (3)	0.75885 (14)	0.0623 (6)
S1	−0.10260 (11)	0.66085 (10)	0.36254 (5)	0.0505 (2)
N1	−0.0930 (4)	0.6076 (4)	0.25432 (17)	0.0473 (6)
C1	0.1545 (4)	0.5777 (3)	0.39509 (17)	0.0355 (5)
C2	0.2470 (4)	0.5106 (3)	0.31860 (17)	0.0369 (5)
C3	0.1002 (4)	0.5291 (3)	0.24041 (17)	0.0375 (5)
C4	0.1477 (4)	0.4669 (3)	0.14826 (17)	0.0391 (5)
C5	0.3554 (5)	0.4910 (5)	0.11364 (19)	0.0482 (6)
C6	0.3930 (6)	0.4388 (6)	0.0261 (2)	0.0627 (9)
C7	0.2257 (6)	0.3597 (5)	−0.0282 (2)	0.0643 (10)
C8	0.0206 (6)	0.3312 (5)	0.0068 (3)	0.0598 (8)
C9	−0.0196 (5)	0.3850 (4)	0.0941 (2)	0.0490 (7)
C10	0.2439 (4)	0.5804 (3)	0.49001 (17)	0.0351 (5)
C11	0.1298 (5)	0.6657 (4)	0.55817 (19)	0.0461 (6)
C12	0.2156 (5)	0.6693 (5)	0.64660 (19)	0.0503 (6)
C13	0.4162 (5)	0.5883 (4)	0.66996 (18)	0.0430 (6)
C14	0.5328 (5)	0.5032 (4)	0.60302 (18)	0.0427 (6)
C15	0.4457 (5)	0.4996 (4)	0.51409 (18)	0.0403 (5)
C16	0.6838 (8)	0.5155 (6)	0.7883 (2)	0.0706 (10)
H2	0.387587	0.459462	0.318032	0.044*
H5	0.469362	0.542442	0.149633	0.058*
H6	0.532215	0.456678	0.002941	0.075*
H7	0.251766	0.326248	−0.087616	0.077*
H8	−0.091138	0.275419	−0.028633	0.072*
H9	−0.158997	0.366739	0.117046	0.059*
H11	−0.005761	0.720686	0.543607	0.055*
H12	0.137634	0.726921	0.691119	0.060*
H14	0.668691	0.449069	0.617911	0.051*
H15	0.523906	0.441921	0.469656	0.048*
H16A	0.665401	0.388862	0.781437	0.106*
H16B	0.717252	0.543204	0.851271	0.106*
H16C	0.803493	0.555074	0.752536	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0806 (16)	0.0688 (15)	0.0369 (10)	0.0052 (13)	−0.0040 (10)	−0.0104 (10)
S1	0.0416 (3)	0.0599 (4)	0.0499 (4)	0.0159 (3)	0.0029 (3)	−0.0015 (3)
N1	0.0395 (12)	0.0548 (14)	0.0470 (13)	0.0073 (10)	−0.0044 (10)	0.0051 (10)
C1	0.0358 (11)	0.0307 (11)	0.0401 (12)	0.0005 (9)	0.0014 (9)	0.0026 (10)
C2	0.0332 (11)	0.0390 (12)	0.0382 (12)	0.0029 (9)	−0.0017 (9)	−0.0004 (10)
C3	0.0361 (12)	0.0353 (11)	0.0408 (13)	−0.0026 (9)	−0.0020 (10)	0.0030 (9)
C4	0.0394 (13)	0.0386 (12)	0.0387 (13)	0.0019 (10)	−0.0059 (10)	0.0020 (9)
C5	0.0391 (14)	0.0637 (17)	0.0414 (14)	0.0005 (12)	−0.0032 (11)	−0.0032 (13)
C6	0.0483 (18)	0.091 (3)	0.0487 (17)	0.0113 (17)	0.0045 (14)	−0.0061 (16)
C7	0.067 (2)	0.082 (2)	0.0428 (16)	0.0203 (18)	−0.0066 (14)	−0.0188 (16)
C8	0.0622 (19)	0.0598 (19)	0.0552 (17)	0.0033 (16)	−0.0200 (15)	−0.0146 (15)
C9	0.0443 (15)	0.0497 (15)	0.0518 (16)	−0.0033 (12)	−0.0106 (12)	−0.0038 (12)
C10	0.0373 (12)	0.0319 (10)	0.0364 (11)	−0.0007 (9)	0.0048 (9)	−0.0018 (9)
C11	0.0453 (13)	0.0452 (13)	0.0480 (14)	0.0094 (13)	0.0048 (10)	−0.0081 (12)
C12	0.0567 (16)	0.0499 (15)	0.0453 (14)	0.0038 (15)	0.0111 (12)	−0.0114 (13)
C13	0.0538 (15)	0.0388 (12)	0.0366 (12)	−0.0044 (11)	0.0049 (11)	−0.0038 (10)
C14	0.0434 (14)	0.0435 (13)	0.0412 (13)	0.0047 (11)	0.0009 (11)	−0.0016 (11)
C15	0.0426 (14)	0.0428 (13)	0.0361 (12)	0.0045 (11)	0.0062 (10)	−0.0037 (10)
C16	0.087 (3)	0.078 (2)	0.0453 (17)	0.003 (2)	−0.0114 (17)	0.0013 (17)

Geometric parameters (Å, º) top

S1—N1	1.644 (3)	C15—H15	0.9300
S1—C1	1.716 (2)	C14—H14	0.9300
O1—C13	1.359 (3)	C12—H12	0.9300
O1—C16	1.399 (5)	C5—C4	1.385 (4)
N1—C3	1.329 (4)	C5—C6	1.374 (5)
C1—C2	1.374 (4)	C5—H5	0.9300
C1—C10	1.471 (3)	C4—C9	1.396 (4)
C3—C2	1.423 (3)	C9—C8	1.378 (5)
C3—C4	1.474 (4)	C9—H9	0.9300
C10—C15	1.389 (4)	C7—C8	1.378 (6)
C10—C11	1.397 (4)	C7—C6	1.387 (5)
C2—H2	0.9300	C7—H7	0.9300
C11—C12	1.376 (4)	C6—H6	0.9300
C11—H11	0.9300	C8—H8	0.9300
C13—C12	1.381 (4)	C16—H16A	0.9600
C13—C14	1.391 (4)	C16—H16B	0.9600
C15—C14	1.385 (4)	C16—H16C	0.9600

N1—S1—C1	96.22 (12)	C13—C12—C11	120.7 (3)
C13—O1—C16	119.1 (3)	C13—C12—H12	119.6
C3—N1—S1	109.17 (18)	C11—C12—H12	119.6
C2—C1—C10	129.6 (2)	C4—C5—C6	120.0 (3)
C2—C1—S1	107.52 (18)	C4—C5—H5	120.0
C10—C1—S1	122.92 (19)	C6—C5—H5	120.0
N1—C3—C2	115.7 (2)	C5—C4—C9	119.2 (3)
N1—C3—C4	119.5 (2)	C5—C4—C3	121.1 (2)
C2—C3—C4	124.8 (2)	C9—C4—C3	119.7 (3)
C15—C10—C11	118.2 (2)	C8—C9—C4	120.3 (3)
C15—C10—C1	120.7 (2)	C8—C9—H9	119.8
C11—C10—C1	121.1 (2)	C4—C9—H9	119.8
C1—C2—C3	111.4 (2)	C8—C7—C6	119.4 (3)
C1—C2—H2	124.3	C8—C7—H7	120.3
C3—C2—H2	124.3	C6—C7—H7	120.3
C12—C11—C10	120.7 (3)	C5—C6—C7	120.8 (3)
C12—C11—H11	119.6	C5—C6—H6	119.6
C10—C11—H11	119.6	C7—C6—H6	119.6
O1—C13—C12	115.9 (3)	C9—C8—C7	120.2 (3)
O1—C13—C14	124.6 (3)	C9—C8—H8	119.9
C12—C13—C14	119.4 (2)	C7—C8—H8	119.9
C10—C15—C14	121.3 (2)	O1—C16—H16A	109.5
C10—C15—H15	119.4	O1—C16—H16B	109.5
C14—C15—H15	119.4	H16A—C16—H16B	109.5
C13—C14—C15	119.7 (3)	O1—C16—H16C	109.5
C13—C14—H14	120.1	H16A—C16—H16C	109.5
C15—C14—H14	120.1	H16B—C16—H16C	109.5

C1—S1—N1—C3	−0.5 (2)	O1—C13—C14—C15	−179.1 (3)
N1—S1—C1—C2	0.9 (2)	C12—C13—C14—C15	−0.5 (4)
N1—S1—C1—C10	−177.9 (2)	C10—C15—C14—C13	0.4 (4)
S1—N1—C3—C2	−0.1 (3)	O1—C13—C12—C11	179.1 (3)
S1—N1—C3—C4	179.4 (2)	C14—C13—C12—C11	0.4 (5)
C2—C1—C10—C15	−3.4 (4)	C10—C11—C12—C13	−0.2 (5)
S1—C1—C10—C15	175.1 (2)	C6—C5—C4—C9	1.7 (5)
C2—C1—C10—C11	175.9 (3)	C6—C5—C4—C3	−177.2 (3)
S1—C1—C10—C11	−5.5 (4)	N1—C3—C4—C5	138.5 (3)
C10—C1—C2—C3	177.7 (2)	C2—C3—C4—C5	−42.1 (4)
S1—C1—C2—C3	−1.1 (3)	N1—C3—C4—C9	−40.4 (4)
N1—C3—C2—C1	0.8 (3)	C2—C3—C4—C9	139.0 (3)
C4—C3—C2—C1	−178.6 (2)	C5—C4—C9—C8	−0.9 (4)
C15—C10—C11—C12	0.0 (5)	C3—C4—C9—C8	178.0 (3)
C1—C10—C11—C12	−179.3 (3)	C4—C5—C6—C7	−0.8 (6)
C16—O1—C13—C12	176.8 (3)	C8—C7—C6—C5	−0.9 (6)
C16—O1—C13—C14	−4.6 (5)	C4—C9—C8—C7	−0.8 (5)
C11—C10—C15—C14	−0.2 (4)	C6—C7—C8—C9	1.7 (6)
C1—C10—C15—C14	179.2 (2)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C1–C3/N1/S1, C4–C9 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···S1	0.93	2.73	3.137 (3)	107
C8—H8···Cg2ⁱ	0.93	2.82	3.503 (4)	132
C12—H12···Cg1ⁱⁱ	0.93	2.88	3.542 (4)	129
C15—H15···Cg3ⁱⁱⁱ	0.93	2.92	3.688 (3)	140

Symmetry codes: (i) −x, y−1/2, −z; (ii) −x, y+1/2, −z+1; (iii) −x+1, y−1/2, −z+1.

Acknowledgements

The authors thank BMSIT&M, Bengaluru and Govt. Engineering College, Chamarajanagara, for laboratory support.

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