(Z)-N-[3-(2-Methoxy­phen­yl)-4-phenyl-2,3-dihydro­thia­zol-2-yl­idene]-4-methyl­benzamide

Saeed, A.; Zaman, S.; Bolte, M.

doi:10.1107/S160053680706165X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o67

https://doi.org/10.1107/S160053680706165X

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(Z)-N-[3-(2-Methoxyphenyl)-4-phenyl-2,3-dihydrothiazol-2-ylidene]-4-methylbenzamide

Aamer Saeed,^a ^* Sabah Zaman ^a and Michael Bolte ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 24 October 2007; accepted 21 November 2007; online 6 December 2007)

Geometric parameters of the title compound, C₂₄H₂₀N₂O₂S, are in the usual ranges. The central heterocycle makes dihedral angles of 41.29 (4) and 72.94 (5)° with the phenyl ring and the methoxyphenyl ring, respectively.

Related literature

For related literature, see: Arcadi et al. (2003 ); Bae et al. (2005 ); Bonde & Gaikwad (2004 ); Kim et al. (2007 ); Lee & Sim (2000 ); Manaka et al. (2005 ); Saeed & Parvez (2006 ); Sanemitsu et al. (2006 ); Shehata et al. (1996 ); Shih & Ke (2004 ); Venkatachalan et al. (2001 ).

Experimental

Crystal data

C₂₄H₂₀N₂O₂S
M_r = 400.48
Monoclinic, P 2₁ /c
a = 10.1305 (10) Å
b = 20.0583 (14) Å
c = 10.0959 (10) Å
β = 102.710 (8)°
V = 2001.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 173 (2) K
0.33 × 0.23 × 0.22 mm

Data collection

Stoe IPDSII two-circlediffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003 ; Blessing, 1995 ) T_min = 0.942, T_max = 0.951
11964 measured reflections
3728 independent reflections
3095 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 1.05
3728 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053680706165X/sg2195sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706165X/sg2195Isup2.hkl

checkCIF report

Comment top

2-Imino derivatives of 1,3-thiazolines posses a wide range of pharmacological and synthetic applications. Thus, these show potent bioactivities ranging from antitubercular (Shehata et al., 1996) to anti-HIV (Venkatachalan et al., 2001) activities. Iminothiazolines containing a pyrazine ring show significant antibacterial and antimicrobial activity (Bonde & Gaikwad 2004), derivatives of rhodanine show antibacterial, anti-inflammatory and antiviral activities (Lee & Sim et al., 2000) and bis-thiazoline derivatives show marked anti-cancer activity against human cell lines (Arcadi et al., 2003). A 2-imino-1,3-thiazoline derivative KHG22394 act as a skin whitening agent (Kim et al., 2007). 4-Phenyl-2-hyrazono?thiazolines exhibit potent DPPH radical scavenging activity (Shih & Ke, 2004). 3-Alkyl-3H-thiazoline derivative PS-028 acts as potent and selective GPllb/llla antagonist (Manaka et al., 2005). 2-Acylimino-1,3-thiazolines show bleaching herbicidal activity (Sanemitsu et al., 2006) and 2-phenylimino-1,3-thiazolines show significant antifungal activity against rice blast fungus Pyricularia oryzae (Bae et al., 2005).

Geometric parameters of the title compound are in the usual ranges. The dihedral angles between the central heterocycle and the phenyl ring is 41.29 (4)and 72.94 (5)° for the methoxyphenyl ring.

Related literature top

For related literature, see: Arcadi et al. (2003); Bae et al. (2005); Bonde & Gaikwad (2004); Kim et al. (2007); Lee & Sim (2000); Manaka et al. (2005); Saeed & Parvez (2006); Sanemitsu et al. (2006); Shehata et al. (1996); Shih & Ke (2004); Venkatachalan et al. (2001).

Experimental top

The title compound was prepared according to the method reported earlier (Saeed & Parvez 2006). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution. Full spectroscopic and physical characterization will be reported elsewhere.

Structure description top

Geometric parameters of the title compound are in the usual ranges. The dihedral angles between the central heterocycle and the phenyl ring is 41.29 (4)and 72.94 (5)° for the methoxyphenyl ring.

For related literature, see: Arcadi et al. (2003); Bae et al. (2005); Bonde & Gaikwad (2004); Kim et al. (2007); Lee & Sim (2000); Manaka et al. (2005); Saeed & Parvez (2006); Sanemitsu et al. (2006); Shehata et al. (1996); Shih & Ke (2004); Venkatachalan et al. (2001).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. Molecular structure of title compound with displacement ellipsoids at the 50% probability level.

(Z)—N-[3-(2-Methoxyphenyl)-4-phenyl-2,3-dihydrothiazol-2-ylidene]- 4-methylbenzamide top

Crystal data top

C₂₄H₂₀N₂O₂S	F(000) = 840
M_r = 400.48	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10726 reflections
a = 10.1305 (10) Å	θ = 3.8–25.8°
b = 20.0583 (14) Å	µ = 0.19 mm⁻¹
c = 10.0959 (10) Å	T = 173 K
β = 102.710 (8)°	Block, colourless
V = 2001.2 (3) Å³	0.33 × 0.23 × 0.22 mm
Z = 4

Data collection top

Stoe IPDSII two-circle diffractometer	3728 independent reflections
Radiation source: fine-focus sealed tube	3095 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 25.6°, θ_min = 3.7°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −12→11
T_min = 0.942, T_max = 0.951	k = −21→24
11964 measured reflections	l = −12→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0627P)² + 0.2151P] where P = (F_o² + 2F_c²)/3
3728 reflections	(Δ/σ)_max = 0.001
264 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₄H₂₀N₂O₂S	V = 2001.2 (3) Å³
M_r = 400.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1305 (10) Å	µ = 0.19 mm⁻¹
b = 20.0583 (14) Å	T = 173 K
c = 10.0959 (10) Å	0.33 × 0.23 × 0.22 mm
β = 102.710 (8)°

Data collection top

Stoe IPDSII two-circle diffractometer	3728 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	3095 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.951	R_int = 0.039
11964 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	Δρ_max = 0.15 e Å⁻³
3728 reflections	Δρ_min = −0.28 e Å⁻³
264 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.98050 (4)	0.70737 (2)	0.51355 (5)	0.04086 (15)
O1	1.10348 (11)	0.68440 (6)	0.31286 (12)	0.0397 (3)
O2	0.72991 (11)	0.52503 (5)	0.53280 (10)	0.0332 (3)
N1	0.75221 (12)	0.64830 (6)	0.43148 (12)	0.0265 (3)
N2	0.89232 (13)	0.63407 (6)	0.27787 (12)	0.0295 (3)
C1	0.87220 (15)	0.65906 (7)	0.39275 (15)	0.0281 (3)
C2	0.74474 (16)	0.67752 (8)	0.55719 (15)	0.0305 (3)
C3	0.86066 (19)	0.70950 (9)	0.61315 (18)	0.0434 (4)
H3	0.8755	0.7311	0.6989	0.052*
C4	1.01248 (15)	0.64968 (7)	0.24281 (15)	0.0303 (3)
C11	1.02529 (15)	0.62264 (8)	0.10802 (15)	0.0301 (3)
C12	0.91665 (16)	0.59116 (8)	0.02041 (16)	0.0347 (4)
H12	0.8335	0.5851	0.0478	0.042*
C13	0.92970 (18)	0.56869 (9)	−0.10637 (17)	0.0396 (4)
H13	0.8548	0.5478	−0.1649	0.047*
C14	1.05099 (17)	0.57628 (9)	−0.14929 (16)	0.0354 (4)
C15	1.15848 (17)	0.60780 (10)	−0.06097 (17)	0.0397 (4)
H15	1.2418	0.6135	−0.0881	0.048*
C16	1.14651 (16)	0.63095 (9)	0.06546 (17)	0.0372 (4)
H16	1.2210	0.6525	0.1232	0.045*
C17	1.0679 (2)	0.54980 (10)	−0.28494 (17)	0.0462 (4)
H17A	1.0897	0.5022	−0.2767	0.069*
H17B	1.1415	0.5738	−0.3130	0.069*
H17C	0.9836	0.5563	−0.3530	0.069*
C21	0.65588 (14)	0.60120 (7)	0.35548 (14)	0.0254 (3)
C22	0.64954 (14)	0.53698 (7)	0.40723 (14)	0.0259 (3)
C23	0.56515 (16)	0.48964 (8)	0.32885 (15)	0.0329 (4)
H23	0.5586	0.4459	0.3629	0.040*
C24	0.49103 (17)	0.50720 (9)	0.20088 (16)	0.0379 (4)
H24	0.4345	0.4749	0.1473	0.045*
C25	0.49813 (17)	0.57099 (9)	0.14992 (16)	0.0387 (4)
H25	0.4464	0.5822	0.0624	0.046*
C26	0.58140 (16)	0.61869 (8)	0.22749 (14)	0.0326 (4)
H26	0.5871	0.6625	0.1933	0.039*
C27	0.74026 (19)	0.45719 (8)	0.58037 (16)	0.0369 (4)
H27A	0.6506	0.4411	0.5872	0.055*
H27B	0.8019	0.4551	0.6699	0.055*
H27C	0.7753	0.4291	0.5164	0.055*
C31	0.62025 (16)	0.67828 (7)	0.61048 (15)	0.0297 (3)
C32	0.63140 (18)	0.67578 (8)	0.75194 (15)	0.0358 (4)
H32	0.7170	0.6677	0.8107	0.043*
C33	0.5178 (2)	0.68500 (8)	0.80611 (17)	0.0415 (4)
H33	0.5264	0.6827	0.9016	0.050*
C34	0.3918 (2)	0.69747 (9)	0.72213 (18)	0.0414 (4)
H34	0.3151	0.7050	0.7600	0.050*
C35	0.37924 (18)	0.69885 (8)	0.58204 (17)	0.0367 (4)
H35	0.2933	0.7068	0.5238	0.044*
C36	0.49179 (16)	0.68870 (7)	0.52706 (15)	0.0313 (3)
H36	0.4815	0.6888	0.4312	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0358 (2)	0.0385 (3)	0.0506 (3)	−0.01358 (18)	0.01446 (18)	−0.01702 (18)
O1	0.0342 (6)	0.0394 (7)	0.0465 (7)	−0.0054 (5)	0.0112 (5)	−0.0059 (5)
O2	0.0418 (6)	0.0246 (5)	0.0292 (5)	−0.0013 (5)	−0.0009 (5)	0.0015 (4)
N1	0.0299 (6)	0.0224 (6)	0.0278 (6)	−0.0030 (5)	0.0074 (5)	−0.0025 (5)
N2	0.0315 (7)	0.0266 (6)	0.0318 (6)	0.0011 (5)	0.0098 (5)	0.0012 (5)
C1	0.0300 (8)	0.0209 (7)	0.0335 (7)	0.0003 (6)	0.0075 (6)	0.0014 (6)
C2	0.0381 (8)	0.0246 (7)	0.0301 (7)	−0.0034 (7)	0.0102 (6)	−0.0061 (6)
C3	0.0458 (10)	0.0424 (10)	0.0444 (9)	−0.0146 (8)	0.0153 (8)	−0.0194 (8)
C4	0.0290 (8)	0.0249 (8)	0.0377 (8)	0.0040 (6)	0.0089 (6)	0.0051 (6)
C11	0.0295 (8)	0.0274 (8)	0.0347 (8)	0.0062 (6)	0.0098 (6)	0.0071 (6)
C12	0.0290 (8)	0.0376 (9)	0.0402 (9)	0.0020 (7)	0.0131 (6)	−0.0002 (7)
C13	0.0342 (9)	0.0455 (10)	0.0393 (9)	0.0014 (7)	0.0088 (7)	−0.0037 (7)
C14	0.0354 (8)	0.0383 (9)	0.0344 (8)	0.0095 (7)	0.0120 (7)	0.0077 (7)
C15	0.0326 (8)	0.0507 (11)	0.0392 (9)	0.0038 (8)	0.0155 (7)	0.0099 (7)
C16	0.0298 (8)	0.0444 (10)	0.0382 (8)	0.0011 (7)	0.0090 (7)	0.0071 (7)
C17	0.0479 (10)	0.0561 (12)	0.0390 (9)	0.0069 (9)	0.0192 (8)	0.0026 (8)
C21	0.0251 (7)	0.0268 (7)	0.0249 (7)	−0.0006 (6)	0.0065 (5)	−0.0047 (5)
C22	0.0259 (7)	0.0269 (8)	0.0252 (7)	0.0000 (6)	0.0062 (6)	−0.0033 (5)
C23	0.0337 (8)	0.0296 (8)	0.0367 (8)	−0.0051 (7)	0.0103 (7)	−0.0074 (6)
C24	0.0332 (9)	0.0449 (10)	0.0342 (8)	−0.0064 (7)	0.0049 (7)	−0.0146 (7)
C25	0.0347 (9)	0.0527 (11)	0.0261 (7)	0.0031 (8)	0.0007 (6)	−0.0055 (7)
C26	0.0350 (8)	0.0357 (9)	0.0269 (7)	0.0044 (7)	0.0065 (6)	0.0011 (6)
C27	0.0517 (10)	0.0259 (8)	0.0336 (8)	0.0036 (7)	0.0102 (7)	0.0035 (6)
C31	0.0389 (8)	0.0202 (7)	0.0319 (7)	−0.0040 (6)	0.0118 (6)	−0.0053 (6)
C32	0.0468 (10)	0.0290 (8)	0.0317 (8)	−0.0007 (7)	0.0091 (7)	−0.0047 (6)
C33	0.0645 (12)	0.0316 (9)	0.0333 (8)	−0.0023 (8)	0.0212 (8)	−0.0042 (7)
C34	0.0509 (10)	0.0318 (9)	0.0492 (10)	−0.0048 (8)	0.0277 (8)	−0.0057 (7)
C35	0.0385 (9)	0.0293 (8)	0.0443 (9)	−0.0025 (7)	0.0134 (7)	−0.0043 (7)
C36	0.0410 (9)	0.0233 (7)	0.0311 (8)	−0.0030 (7)	0.0110 (6)	−0.0025 (6)

Geometric parameters (Å, º) top

S1—C3	1.7390 (19)	C17—H17B	0.9800
S1—C1	1.7439 (15)	C17—H17C	0.9800
O1—C4	1.2442 (19)	C21—C26	1.3903 (19)
O2—C22	1.3687 (17)	C21—C22	1.397 (2)
O2—C27	1.4392 (18)	C22—C23	1.400 (2)
N1—C1	1.373 (2)	C23—C24	1.389 (2)
N1—C2	1.4151 (19)	C23—H23	0.9500
N1—C21	1.4505 (17)	C24—C25	1.387 (3)
N2—C1	1.320 (2)	C24—H24	0.9500
N2—C4	1.376 (2)	C25—C26	1.396 (2)
C2—C3	1.348 (2)	C25—H25	0.9500
C2—C31	1.476 (2)	C26—H26	0.9500
C3—H3	0.9500	C27—H27A	0.9800
C4—C11	1.497 (2)	C27—H27B	0.9800
C11—C16	1.397 (2)	C27—H27C	0.9800
C11—C12	1.401 (2)	C31—C36	1.402 (2)
C12—C13	1.390 (2)	C31—C32	1.409 (2)
C12—H12	0.9500	C32—C33	1.390 (2)
C13—C14	1.398 (2)	C32—H32	0.9500
C13—H13	0.9500	C33—C34	1.391 (3)
C14—C15	1.398 (2)	C33—H33	0.9500
C14—C17	1.514 (2)	C34—C35	1.392 (2)
C15—C16	1.388 (2)	C34—H34	0.9500
C15—H15	0.9500	C35—C36	1.388 (2)
C16—H16	0.9500	C35—H35	0.9500
C17—H17A	0.9800	C36—H36	0.9500

C3—S1—C1	90.36 (8)	C26—C21—C22	121.34 (13)
C22—O2—C27	117.35 (11)	C26—C21—N1	119.45 (14)
C1—N1—C2	114.55 (12)	C22—C21—N1	118.93 (12)
C1—N1—C21	119.11 (12)	O2—C22—C21	116.16 (12)
C2—N1—C21	125.57 (13)	O2—C22—C23	124.72 (14)
C1—N2—C4	117.12 (13)	C21—C22—C23	119.12 (13)
N2—C1—N1	120.52 (13)	C24—C23—C22	119.43 (15)
N2—C1—S1	129.09 (12)	C24—C23—H23	120.3
N1—C1—S1	110.39 (10)	C22—C23—H23	120.3
C3—C2—N1	111.07 (14)	C25—C24—C23	121.16 (14)
C3—C2—C31	125.28 (14)	C25—C24—H24	119.4
N1—C2—C31	123.35 (13)	C23—C24—H24	119.4
C2—C3—S1	113.61 (12)	C24—C25—C26	119.89 (14)
C2—C3—H3	123.2	C24—C25—H25	120.1
S1—C3—H3	123.2	C26—C25—H25	120.1
O1—C4—N2	124.59 (15)	C21—C26—C25	119.06 (15)
O1—C4—C11	121.19 (15)	C21—C26—H26	120.5
N2—C4—C11	114.19 (13)	C25—C26—H26	120.5
C16—C11—C12	118.75 (15)	O2—C27—H27A	109.5
C16—C11—C4	119.62 (14)	O2—C27—H27B	109.5
C12—C11—C4	121.59 (14)	H27A—C27—H27B	109.5
C13—C12—C11	120.43 (16)	O2—C27—H27C	109.5
C13—C12—H12	119.8	H27A—C27—H27C	109.5
C11—C12—H12	119.8	H27B—C27—H27C	109.5
C12—C13—C14	121.20 (16)	C36—C31—C32	118.12 (15)
C12—C13—H13	119.4	C36—C31—C2	122.50 (13)
C14—C13—H13	119.4	C32—C31—C2	119.00 (14)
C15—C14—C13	117.78 (15)	C33—C32—C31	120.35 (15)
C15—C14—C17	120.57 (16)	C33—C32—H32	119.8
C13—C14—C17	121.64 (16)	C31—C32—H32	119.8
C16—C15—C14	121.64 (16)	C32—C33—C34	120.80 (15)
C16—C15—H15	119.2	C32—C33—H33	119.6
C14—C15—H15	119.2	C34—C33—H33	119.6
C15—C16—C11	120.21 (15)	C33—C34—C35	119.30 (17)
C15—C16—H16	119.9	C33—C34—H34	120.4
C11—C16—H16	119.9	C35—C34—H34	120.4
C14—C17—H17A	109.5	C36—C35—C34	120.24 (16)
C14—C17—H17B	109.5	C36—C35—H35	119.9
H17A—C17—H17B	109.5	C34—C35—H35	119.9
C14—C17—H17C	109.5	C35—C36—C31	121.14 (14)
H17A—C17—H17C	109.5	C35—C36—H36	119.4
H17B—C17—H17C	109.5	C31—C36—H36	119.4

C4—N2—C1—N1	176.95 (12)	C4—C11—C16—C15	−178.16 (15)
C4—N2—C1—S1	−3.0 (2)	C1—N1—C21—C26	−73.97 (18)
C2—N1—C1—N2	179.56 (13)	C2—N1—C21—C26	116.67 (16)
C21—N1—C1—N2	9.1 (2)	C1—N1—C21—C22	99.99 (16)
C2—N1—C1—S1	−0.48 (15)	C2—N1—C21—C22	−69.38 (19)
C21—N1—C1—S1	−170.98 (10)	C27—O2—C22—C21	−171.39 (14)
C3—S1—C1—N2	−178.83 (15)	C27—O2—C22—C23	7.6 (2)
C3—S1—C1—N1	1.21 (12)	C26—C21—C22—O2	178.36 (13)
C1—N1—C2—C3	−0.81 (19)	N1—C21—C22—O2	4.5 (2)
C21—N1—C2—C3	168.98 (15)	C26—C21—C22—C23	−0.7 (2)
C1—N1—C2—C31	173.17 (13)	N1—C21—C22—C23	−174.56 (13)
C21—N1—C2—C31	−17.0 (2)	O2—C22—C23—C24	−178.17 (15)
N1—C2—C3—S1	1.76 (19)	C21—C22—C23—C24	0.8 (2)
C31—C2—C3—S1	−172.09 (12)	C22—C23—C24—C25	−0.6 (2)
C1—S1—C3—C2	−1.74 (15)	C23—C24—C25—C26	0.3 (3)
C1—N2—C4—O1	1.4 (2)	C22—C21—C26—C25	0.4 (2)
C1—N2—C4—C11	−176.94 (12)	N1—C21—C26—C25	174.20 (14)
O1—C4—C11—C16	6.2 (2)	C24—C25—C26—C21	−0.2 (2)
N2—C4—C11—C16	−175.35 (13)	C3—C2—C31—C36	134.02 (18)
O1—C4—C11—C12	−171.36 (15)	N1—C2—C31—C36	−39.1 (2)
N2—C4—C11—C12	7.1 (2)	C3—C2—C31—C32	−38.8 (2)
C16—C11—C12—C13	0.0 (2)	N1—C2—C31—C32	148.05 (15)
C4—C11—C12—C13	177.59 (15)	C36—C31—C32—C33	−1.4 (2)
C11—C12—C13—C14	0.6 (3)	C2—C31—C32—C33	171.72 (14)
C12—C13—C14—C15	−0.6 (3)	C31—C32—C33—C34	−0.6 (3)
C12—C13—C14—C17	177.76 (16)	C32—C33—C34—C35	1.8 (3)
C13—C14—C15—C16	0.1 (3)	C33—C34—C35—C36	−0.8 (2)
C17—C14—C15—C16	−178.30 (16)	C34—C35—C36—C31	−1.3 (2)
C14—C15—C16—C11	0.5 (3)	C32—C31—C36—C35	2.4 (2)
C12—C11—C16—C15	−0.5 (2)	C2—C31—C36—C35	−170.49 (14)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₂O₂S
M_r	400.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	10.1305 (10), 20.0583 (14), 10.0959 (10)
β (°)	102.710 (8)
V (Å³)	2001.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.33 × 0.23 × 0.22

Data collection
Diffractometer	Stoe IPDSII two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.942, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	11964, 3728, 3095
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.05
No. of reflections	3728
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.28

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Acknowledgements

AS gratefully acknowledges a research grant from the Quaid-i-Azam University, Islamabad, Pakistan.

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