4-Hy­droxy-6-(4-meth­oxy­phen­yl)-4-phenyl-1,3-diazinane-2-thione

Devarajegowda, H.C.; Roopashree, K.R.; Mohammed, I.A.; Mahalakshmi; Sankolli, R.

doi:10.1107/S1600536811008002

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o815

doi:10.1107/S1600536811008002

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4-Hydroxy-6-(4-methoxyphenyl)-4-phenyl-1,3-diazinane-2-thione

H. C. Devarajegowda,^a ^* K. R. Roopashree,^a Irfan Ali Mohammed,^b Mahalakshmi ^a and Ravish Sankolli ^c

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, ^bDepartment of Pharmaceutical Chemistry, Sri Adichunchangiri College of Pharmacy, B.G. Nagar 571 448, Mandya, Karnataka, India, and ^cSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 12, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 21 January 2011; accepted 3 March 2011; online 9 March 2011)

In the title compound, C₁₇H₁₈N₂O₂S, the 1,3-diazinane-2-thione ring system is not coplanar with the benzene ring and methoxyphenyl ring system, the dihedral angle between the planes being 65.58 (13) and 89.18 (10)°, respectively. The crystal structure is characterized by intermolecular O—H⋯S, N—H⋯S, N—H⋯O and C—H⋯S hydrogen bonding.

Related literature

For general background to pyrimidines, see: Cheng (1969 ); Scott et al. (1959 ); Jonak et al. (1972 ); Falco et al. (1961 ); Ram (1990 ); Howells et al. (1981 ); Pershin et al. (1972 ); Matolcsy (1971 ); Prikazchikova et al. (1975 ). For the synthesis, see: Paghdar et al. (2007 ). For a related structure, see: Yamin et al. (2005 ).

Experimental

Crystal data

C₁₇H₁₈N₂O₂S
M_r = 314.39
Monoclinic, P 2₁ /c
a = 12.6016 (3) Å
b = 6.3375 (1) Å
c = 20.6637 (4) Å
β = 97.890 (2)°
V = 1634.64 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 K
0.18 × 0.16 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.963, T_max = 1.000
18135 measured reflections
3547 independent reflections
2566 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.115
S = 1.08
3547 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯S1ⁱ	0.88 (3)	2.51 (3)	3.3688 (18)	169 (2)
C14—H14⋯S1ⁱ	1.030 (19)	2.695 (18)	3.666 (2)	157.0 (14)
N4—H4⋯S1ⁱⁱ	0.86	2.47	3.2990 (19)	163
N5—H5⋯O3ⁱⁱⁱ	0.86	2.18	3.032 (2)	169
C20—H20⋯S1^iv	0.93	2.86	3.772 (2)	166
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+1; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008002/bv2177sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008002/bv2177Isup2.hkl

checkCIF report

Comment top

Pyrimidines, being an integral part of DNA and RNA, exhibit diverse pharmacological properties as effective bactericide, fungicide, viricide, insecticide, and medicinal agents (Cheng, 1969; Scott et al., 1959). Certain pyrimidines and annulated pyrimidine derivatives are also known to display anticancer, antimalarial, antileishmanial and antifilarial activities (Jonak et al., 1972; Falco et al. 1961; Ram, 1990; Howells et al., 1981). Pyrimidines and thio-pyrimidines play an essential role in several biological processes and have a considerable chemical and pharmacological importance. In particular, the pyrimidine nucleus can be found in a broad variety of antibacterial and antitumor agents as well as in agrochemical and veterinary products (Pershin et al., 1972; Matolcsy, 1971; Prikazchikova et al., 1975).

The asymmetric unit of the 4-hydroxy-6-(4-methoxyphenyl)-4-phenyl tetrahydropyrimidine-2(1H)-thione contains one molecule (Fig. 1). The thio-tetrahydropyrimidine ring system is not coplanar with the benzene ring and methoxyphenyl ring system; the dihedral angle between the two planes 65.58 (13)° and 89.18 (10)° respectively. The crystal structure shows intermolecular O2—H2···S1, N4—H4···S1, N5—H5···O3, C14—H14···S1 & C20—H20···S1 and C6—H6···S1 intramolecular hydrogen bonds. Bond distances and bond angles within the aromatic rings are in agreement with those observed in a related structure (Yamin et al., 2005).

Related literature top

For general background to pyrimidines, see: Cheng (1969); Scott et al. (1959); Jonak et al. (1972); Falco et al. (19612); Ram (1990); Howells et al. (1981); Pershin et al. (1972); Matolcsy (1971); Prikazchikova et al. (1975). For synthesis, see: Paghdar et al. (2007). For a related structure, see: Yamin et al. (2005).

Experimental top

A general procedure for the synthesis of 4-hydroxy-6-(4-methoxyphenyl)- 4-phenyl-3,4-dihydropyrimidine-2(1H)-thione is given in Paghdar et al., 2007. An equimolar mixture of (2E)-1,3-diphenylprop-2-en-1-one and thiourea (0.01 mol) were dissolved in minimum amount of ethanol. Potassium hydroxide solution (2.5 ml) was added slowly and the mixture stirred for 10 h until the entire mixture becomes very cloudy. Then the mixture was neutralized with 10% HCl and poured slowly into 100 ml of cold water with constant stirring. The precipitate obtained was filtered, washed and recrystallized from ethanol.

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2010); data reduction: CrysAlis PRO RED (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 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds
	Fig. 2. A packing view of the structure down the axis b.

4-Hydroxy-6-(4-methoxyphenyl)-4-phenyl-1,3-diazinane-2-thione top

Crystal data top

C₁₇H₁₈N₂O₂S	F(000) = 664
M_r = 314.39	D_x = 1.278 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 392 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.6016 (3) Å	Cell parameters from 3547 reflections
b = 6.3375 (1) Å	θ = 2.4–27.0°
c = 20.6637 (4) Å	µ = 0.21 mm⁻¹
β = 97.890 (2)°	T = 295 K
V = 1634.64 (6) Å³	Plate, colourless
Z = 4	0.18 × 0.16 × 0.16 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	3547 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2566 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 16.0839 pixels mm^-1	θ_max = 27.0°, θ_min = 2.4°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	k = −8→7
T_min = 0.963, T_max = 1.000	l = −26→26
18135 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0447P)² + 0.3347P] where P = (F_o² + 2F_c²)/3
3547 reflections	(Δ/σ)_max < 0.001
215 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₇H₁₈N₂O₂S	V = 1634.64 (6) Å³
M_r = 314.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6016 (3) Å	µ = 0.21 mm⁻¹
b = 6.3375 (1) Å	T = 295 K
c = 20.6637 (4) Å	0.18 × 0.16 × 0.16 mm
β = 97.890 (2)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	3547 independent reflections
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	2566 reflections with I > 2σ(I)
T_min = 0.963, T_max = 1.000	R_int = 0.039
18135 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.24 e Å⁻³
3547 reflections	Δρ_min = −0.17 e Å⁻³
215 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05–01–2010 CrysAlis171. NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations 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 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 > 2σ(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	0.48694 (4)	0.81337 (8)	0.41473 (2)	0.04465 (17)
O2	0.28051 (14)	0.2485 (2)	0.48527 (8)	0.0550 (4)
O3	0.32640 (13)	1.1217 (2)	0.79728 (7)	0.0595 (4)
N4	0.40048 (13)	0.7486 (3)	0.52278 (7)	0.0431 (4)
H4	0.4430	0.8470	0.5390	0.052*
N5	0.32830 (12)	0.5582 (2)	0.43340 (7)	0.0430 (4)
H5	0.3310	0.5243	0.3934	0.052*
C6	0.08485 (19)	0.2493 (4)	0.41656 (13)	0.0669 (7)
H6	0.1074	0.1390	0.4448	0.080*
C7	−0.0087 (2)	0.2288 (5)	0.37313 (17)	0.0873 (9)
H7	−0.0479	0.1044	0.3725	0.105*
C8	−0.0434 (2)	0.3852 (7)	0.33198 (16)	0.0943 (10)
H8	−0.1061	0.3690	0.3029	0.113*
C9	0.0139 (2)	0.5698 (6)	0.33308 (15)	0.0935 (9)
H9	−0.0101	0.6793	0.3049	0.112*
C10	0.1081 (2)	0.5928 (4)	0.37639 (13)	0.0715 (7)
H10	0.1466	0.7182	0.3770	0.086*
C11	0.14488 (16)	0.4324 (3)	0.41824 (10)	0.0464 (5)
C12	0.24682 (15)	0.4557 (3)	0.46603 (9)	0.0423 (5)
C13	0.22823 (17)	0.5908 (4)	0.52483 (10)	0.0474 (5)
C14	0.33350 (16)	0.6441 (3)	0.56604 (9)	0.0421 (5)
C15	0.39945 (14)	0.7009 (3)	0.46044 (9)	0.0369 (4)
C16	0.32722 (15)	0.7792 (3)	0.62573 (9)	0.0397 (4)
C17	0.27293 (16)	0.9682 (3)	0.62387 (9)	0.0454 (5)
H17	0.2372	1.0162	0.5842	0.055*
C18	0.27031 (16)	1.0888 (3)	0.67978 (9)	0.0456 (5)
H18	0.2329	1.2157	0.6776	0.055*
C19	0.32394 (16)	1.0182 (3)	0.73856 (9)	0.0442 (5)
C20	0.38044 (19)	0.8316 (4)	0.74086 (10)	0.0568 (6)
H20	0.4175	0.7849	0.7803	0.068*
C21	0.38211 (18)	0.7138 (3)	0.68487 (10)	0.0521 (5)
H21	0.4208	0.5885	0.6869	0.063*
C22	0.2770 (3)	1.3220 (4)	0.79812 (12)	0.0780 (8)
H22A	0.2851	1.3747	0.8421	0.117*
H22B	0.2022	1.3093	0.7818	0.117*
H22C	0.3101	1.4179	0.7710	0.117*
H2	0.345 (2)	0.244 (4)	0.5073 (14)	0.081 (9)*
H13A	0.1920 (17)	0.726 (3)	0.5100 (10)	0.054 (6)*
H13B	0.1841 (16)	0.512 (3)	0.5504 (10)	0.054 (6)*
H14	0.3700 (14)	0.504 (3)	0.5815 (9)	0.045 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0494 (3)	0.0552 (3)	0.0309 (3)	−0.0148 (2)	0.0107 (2)	−0.0048 (2)
O2	0.0585 (10)	0.0531 (9)	0.0499 (9)	−0.0108 (8)	−0.0050 (8)	0.0045 (7)
O3	0.0839 (11)	0.0644 (10)	0.0302 (7)	0.0027 (8)	0.0081 (7)	−0.0087 (7)
N4	0.0473 (9)	0.0555 (10)	0.0274 (8)	−0.0184 (8)	0.0085 (7)	−0.0080 (7)
N5	0.0476 (9)	0.0550 (10)	0.0273 (8)	−0.0169 (8)	0.0091 (7)	−0.0080 (7)
C6	0.0521 (14)	0.0733 (16)	0.0741 (17)	−0.0193 (12)	0.0038 (12)	−0.0066 (13)
C7	0.0505 (16)	0.109 (2)	0.099 (2)	−0.0249 (16)	−0.0020 (16)	−0.028 (2)
C8	0.0495 (16)	0.148 (3)	0.079 (2)	−0.002 (2)	−0.0135 (14)	−0.032 (2)
C9	0.0699 (19)	0.129 (3)	0.074 (2)	0.0122 (19)	−0.0166 (15)	0.0102 (19)
C10	0.0617 (15)	0.0838 (17)	0.0648 (17)	−0.0053 (14)	−0.0065 (13)	0.0077 (14)
C11	0.0424 (11)	0.0614 (13)	0.0356 (10)	−0.0074 (10)	0.0068 (9)	−0.0083 (9)
C12	0.0442 (11)	0.0490 (11)	0.0338 (10)	−0.0113 (9)	0.0061 (8)	−0.0011 (9)
C13	0.0492 (12)	0.0613 (14)	0.0335 (11)	−0.0173 (11)	0.0122 (9)	−0.0069 (10)
C14	0.0493 (11)	0.0496 (12)	0.0278 (10)	−0.0084 (10)	0.0072 (8)	−0.0008 (8)
C15	0.0373 (10)	0.0436 (10)	0.0293 (9)	−0.0026 (8)	0.0028 (8)	−0.0008 (8)
C16	0.0418 (10)	0.0504 (11)	0.0276 (9)	−0.0110 (9)	0.0076 (8)	−0.0007 (8)
C17	0.0509 (12)	0.0593 (13)	0.0251 (9)	−0.0048 (10)	0.0015 (8)	0.0054 (9)
C18	0.0528 (12)	0.0487 (11)	0.0362 (11)	−0.0010 (10)	0.0093 (9)	0.0011 (9)
C19	0.0541 (12)	0.0522 (12)	0.0273 (9)	−0.0091 (10)	0.0091 (9)	−0.0020 (8)
C20	0.0732 (15)	0.0646 (14)	0.0294 (11)	0.0062 (12)	−0.0038 (10)	0.0006 (10)
C21	0.0633 (14)	0.0564 (13)	0.0352 (11)	0.0064 (11)	0.0016 (10)	−0.0011 (9)
C22	0.134 (3)	0.0563 (15)	0.0468 (14)	−0.0004 (15)	0.0242 (15)	−0.0084 (11)

Geometric parameters (Å, º) top

S1—C15	1.7033 (18)	C10—H10	0.9300
O2—C12	1.420 (2)	C11—C12	1.516 (3)
O2—H2	0.87 (3)	C12—C13	1.531 (3)
O3—C19	1.376 (2)	C13—C14	1.513 (3)
O3—C22	1.415 (3)	C13—H13A	1.00 (2)
N4—C15	1.321 (2)	C13—H13B	0.96 (2)
N4—C14	1.469 (2)	C14—C16	1.513 (3)
N4—H4	0.8600	C14—H14	1.029 (19)
N5—C15	1.340 (2)	C16—C17	1.377 (3)
N5—C12	1.456 (2)	C16—C21	1.382 (3)
N5—H5	0.8600	C17—C18	1.390 (3)
C6—C11	1.383 (3)	C17—H17	0.9300
C6—C7	1.386 (4)	C18—C19	1.381 (3)
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.340 (4)	C19—C20	1.378 (3)
C7—H7	0.9300	C20—C21	1.379 (3)
C8—C9	1.374 (5)	C20—H20	0.9300
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.393 (4)	C22—H22A	0.9600
C9—H9	0.9300	C22—H22B	0.9600
C10—C11	1.373 (3)	C22—H22C	0.9600

C12—O2—H2	113.2 (17)	C12—C13—H13B	108.1 (12)
C19—O3—C22	118.80 (17)	H13A—C13—H13B	109.9 (17)
C15—N4—C14	124.10 (16)	N4—C14—C16	109.86 (15)
C15—N4—H4	117.9	N4—C14—C13	106.90 (16)
C14—N4—H4	117.9	C16—C14—C13	116.45 (17)
C15—N5—C12	125.57 (15)	N4—C14—H14	107.9 (10)
C15—N5—H5	117.2	C16—C14—H14	107.9 (11)
C12—N5—H5	117.2	C13—C14—H14	107.6 (11)
C11—C6—C7	120.6 (3)	N4—C15—N5	118.50 (16)
C11—C6—H6	119.7	N4—C15—S1	121.63 (14)
C7—C6—H6	119.7	N5—C15—S1	119.87 (13)
C8—C7—C6	121.1 (3)	C17—C16—C21	118.15 (18)
C8—C7—H7	119.4	C17—C16—C14	123.44 (17)
C6—C7—H7	119.4	C21—C16—C14	118.37 (19)
C7—C8—C9	119.6 (3)	C16—C17—C18	121.58 (18)
C7—C8—H8	120.2	C16—C17—H17	119.2
C9—C8—H8	120.2	C18—C17—H17	119.2
C8—C9—C10	120.0 (3)	C19—C18—C17	119.23 (19)
C8—C9—H9	120.0	C19—C18—H18	120.4
C10—C9—H9	120.0	C17—C18—H18	120.4
C11—C10—C9	120.7 (3)	O3—C19—C20	115.45 (18)
C11—C10—H10	119.6	O3—C19—C18	124.77 (19)
C9—C10—H10	119.6	C20—C19—C18	119.79 (18)
C10—C11—C6	118.0 (2)	C19—C20—C21	120.2 (2)
C10—C11—C12	121.35 (19)	C19—C20—H20	119.9
C6—C11—C12	120.7 (2)	C21—C20—H20	119.9
O2—C12—N5	109.84 (16)	C20—C21—C16	121.1 (2)
O2—C12—C11	106.63 (16)	C20—C21—H21	119.5
N5—C12—C11	109.27 (15)	C16—C21—H21	119.5
O2—C12—C13	111.57 (17)	O3—C22—H22A	109.5
N5—C12—C13	108.21 (15)	O3—C22—H22B	109.5
C11—C12—C13	111.30 (16)	H22A—C22—H22B	109.5
C14—C13—C12	110.72 (17)	O3—C22—H22C	109.5
C14—C13—H13A	108.1 (12)	H22A—C22—H22C	109.5
C12—C13—H13A	110.4 (12)	H22B—C22—H22C	109.5
C14—C13—H13B	109.6 (12)

C11—C6—C7—C8	−0.2 (4)	C12—C13—C14—N4	56.3 (2)
C6—C7—C8—C9	−0.5 (5)	C12—C13—C14—C16	179.46 (17)
C7—C8—C9—C10	0.5 (5)	C14—N4—C15—N5	4.5 (3)
C8—C9—C10—C11	0.1 (4)	C14—N4—C15—S1	−174.57 (15)
C9—C10—C11—C6	−0.8 (4)	C12—N5—C15—N4	3.2 (3)
C9—C10—C11—C12	−179.5 (2)	C12—N5—C15—S1	−177.72 (15)
C7—C6—C11—C10	0.9 (4)	N4—C14—C16—C17	69.8 (2)
C7—C6—C11—C12	179.6 (2)	C13—C14—C16—C17	−51.9 (3)
C15—N5—C12—O2	−101.5 (2)	N4—C14—C16—C21	−107.7 (2)
C15—N5—C12—C11	141.84 (19)	C13—C14—C16—C21	130.6 (2)
C15—N5—C12—C13	20.5 (3)	C21—C16—C17—C18	−1.7 (3)
C10—C11—C12—O2	−161.1 (2)	C14—C16—C17—C18	−179.17 (18)
C6—C11—C12—O2	20.3 (2)	C16—C17—C18—C19	0.4 (3)
C10—C11—C12—N5	−42.4 (3)	C22—O3—C19—C20	175.4 (2)
C6—C11—C12—N5	138.9 (2)	C22—O3—C19—C18	−4.4 (3)
C10—C11—C12—C13	77.0 (3)	C17—C18—C19—O3	−179.22 (18)
C6—C11—C12—C13	−101.6 (2)	C17—C18—C19—C20	1.0 (3)
O2—C12—C13—C14	70.8 (2)	O3—C19—C20—C21	179.17 (19)
N5—C12—C13—C14	−50.2 (2)	C18—C19—C20—C21	−1.0 (3)
C11—C12—C13—C14	−170.27 (18)	C19—C20—C21—C16	−0.3 (3)
C15—N4—C14—C16	−161.66 (18)	C17—C16—C21—C20	1.6 (3)
C15—N4—C14—C13	−34.5 (3)	C14—C16—C21—C20	179.26 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···S1ⁱ	0.88 (3)	2.51 (3)	3.3688 (18)	169 (2)
C14—H14···S1ⁱ	1.030 (19)	2.695 (18)	3.666 (2)	157.0 (14)
N4—H4···S1ⁱⁱ	0.86	2.47	3.2990 (19)	163
N5—H5···O3ⁱⁱⁱ	0.86	2.18	3.032 (2)	169
C20—H20···S1^iv	0.93	2.86	3.772 (2)	166
C6—H6···O2	0.93	2.33	2.671 (3)	101

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, −y+3/2, z−1/2; (iv) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₂S
M_r	314.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	12.6016 (3), 6.3375 (1), 20.6637 (4)
β (°)	97.890 (2)
V (Å³)	1634.64 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.18 × 0.16 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)
T_min, T_max	0.963, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	18135, 3547, 2566
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.115, 1.08
No. of reflections	3547
No. of parameters	215
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.17

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2010), CrysAlis PRO RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···S1ⁱ	0.88 (3)	2.51 (3)	3.3688 (18)	169 (2)
C14—H14···S1ⁱ	1.030 (19)	2.695 (18)	3.666 (2)	157.0 (14)
N4—H4···S1ⁱⁱ	0.86	2.47	3.2990 (19)	163
N5—H5···O3ⁱⁱⁱ	0.86	2.18	3.032 (2)	169
C20—H20···S1^iv	0.93	2.86	3.772 (2)	166

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, −y+3/2, z−1/2; (iv) x, −y+3/2, z+1/2.

Acknowledgements

The authors thank Professor T. N. Guru Row and Mr Venkatesha R. Hathwar, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for their help with the data collection.

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