1-[1-(3-Methyl­phen­yl)-5-phenyl-4-phenyl­sulfonyl-1H-pyrazol-3-yl]ethanone

Ghazzali, M.; Abdel-Aziz, H.A.; Al-Farhan, K.; Ng, S.W.

doi:10.1107/S1600536811041122

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2922

doi:10.1107/S1600536811041122

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1-[1-(3-Methylphenyl)-5-phenyl-4-phenylsulfonyl-1H-pyrazol-3-yl]ethanone

Mohamed Ghazzali,^a Hatem A. Abdel-Aziz,^b Khalid Al-Farhan ^d and Seik Weng Ng ^c,^a ^*

^aDepartment of Chemistry, Faculty of Science, King Saud University, PO 2455 Riyadh 11451, Saudi Arabia, ^bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, King Saud University, PO Box 2457 Riyadh 11451, Saudi Arabia, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 4 October 2011; accepted 6 October 2011; online 12 October 2011)

Both the acetyl and phenyl substituents of the central pyrazole ring in the title compound, C₂₄H₂₀N₂O₃S, are twisted with respect to the pyrazole ring, with the twist involving the phenyl ring being greater [67.4 (1) and 29.6 (2)°]. The tolyl substituent is disordered over two positions in a 1:1 ratio; the mean planes of the aromatic ring are aligned at 67.7 (3) and 69.4 (3)° with respect to the pyrazole ring.

Related literature

For the synthesis of this class of pyrazoles, which have been tested as anti-inflammatory agents, see: Nasser et al. (2011 ).

Experimental

Crystal data

C₂₄H₂₀N₂O₃S
M_r = 416.48
Monoclinic, P 2₁ /n
a = 10.5717 (4) Å
b = 17.7004 (6) Å
c = 12.8744 (4) Å
β = 115.945 (1)°
V = 2166.30 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.933, T_max = 0.966
23603 measured reflections
4951 independent reflections
3490 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.131
S = 1.16
4951 reflections
266 parameters
44 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811041122/hg5108sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041122/hg5108Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041122/hg5108Isup3.cml

checkCIF report

Comment top

1-[1-(3-Methylphenyl)-5-phenyl-4-(phenylsulfanyl)-1H-pyrazol-3-yl]ethanone (Scheme I) exhibited excellent activity compared with a standard drug, indomethacin, when tested as an anti-inflammatory chemical. The high activity has been rationalized by using molecular docking (Nasser et al., 2011). Both the acetyl and phenyl substituents of the central pyrazole ring are twisted with respect to the pyrazole ring, with the twist involving the phenyl ring being greater (67.4 (1) ° and 29.6 (2) °). The tolyl substituent is disordered over two positions in a 1:1 ratio; the mean planes of the aromatic ring are aligned at 67.7 (3) ° and 69.4 (3) ° (Fig. 1).

Related literature top

For the synthesis of this class of pyrazoles, which have been tested as anti-inflammatory agents, see: Nasser et al. (2011).

Experimental top

We have recently reported the synthesis of the compound (Nasser et al., 2011). Crystals were obtained upon recrystallization from ethanol suitable for X-ray structural analysis was obtained by slow evaporation from ethanolic solution at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the title compound at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disordered tolyl component is not shown.

1-[1-(3-Methylphenyl)-5-phenyl-4-phenylsulfonyl-1H-pyrazol-3-yl]ethanone top

Crystal data top

C₂₄H₂₀N₂O₃S	F(000) = 872
M_r = 416.48	D_x = 1.277 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 725 reflections
a = 10.5717 (4) Å	θ = 3.1–27.5°
b = 17.7004 (6) Å	µ = 0.18 mm⁻¹
c = 12.8744 (4) Å	T = 293 K
β = 115.945 (1)°	Block, yellow
V = 2166.30 (13) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4951 independent reflections
Radiation source: fine-focus sealed tube	3490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −13→13
T_min = 0.933, T_max = 0.966	k = −22→22
23603 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0582P)² + 0.3317P] where P = (F_o² + 2F_c²)/3
S = 1.16	(Δ/σ)_max = 0.001
4951 reflections	Δρ_max = 0.30 e Å⁻³
266 parameters	Δρ_min = −0.37 e Å⁻³
44 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0235 (19)

Crystal data top

C₂₄H₂₀N₂O₃S	V = 2166.30 (13) Å³
M_r = 416.48	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.5717 (4) Å	µ = 0.18 mm⁻¹
b = 17.7004 (6) Å	T = 293 K
c = 12.8744 (4) Å	0.40 × 0.30 × 0.20 mm
β = 115.945 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4951 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	3490 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.966	R_int = 0.042
23603 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	44 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.16	Δρ_max = 0.30 e Å⁻³
4951 reflections	Δρ_min = −0.37 e Å⁻³
266 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.54751 (5)	0.63143 (2)	0.45045 (4)	0.03997 (16)
O1	0.40174 (15)	0.64090 (7)	0.42277 (13)	0.0545 (4)
O2	0.64729 (16)	0.62701 (7)	0.56934 (11)	0.0534 (4)
O3	0.88191 (16)	0.55753 (8)	0.54515 (13)	0.0637 (4)
N1	0.50448 (17)	0.45192 (8)	0.26398 (13)	0.0440 (4)
N2	0.63866 (17)	0.43781 (9)	0.34261 (13)	0.0460 (4)
C1	0.8879 (2)	0.42371 (13)	0.5538 (2)	0.0624 (6)
H1A	0.9853	0.4310	0.6057	0.094*
H1B	0.8804	0.3920	0.4909	0.094*
H1C	0.8409	0.4001	0.5944	0.094*
C2	0.8211 (2)	0.49846 (11)	0.50784 (17)	0.0452 (4)
C3	0.67586 (19)	0.49709 (9)	0.41353 (15)	0.0405 (4)
C4	0.56201 (19)	0.54928 (9)	0.38003 (14)	0.0382 (4)
C5	0.45247 (19)	0.51785 (9)	0.28374 (15)	0.0388 (4)
C6	0.3067 (2)	0.54191 (10)	0.21258 (15)	0.0431 (4)
C7	0.1966 (2)	0.50136 (12)	0.21653 (18)	0.0551 (5)
H7	0.2151	0.4584	0.2624	0.066*
C8	0.0593 (2)	0.52496 (16)	0.1521 (2)	0.0722 (7)
H8	−0.0146	0.4975	0.1542	0.087*
C9	0.0319 (3)	0.58849 (17)	0.0853 (2)	0.0803 (7)
H9	−0.0604	0.6048	0.0437	0.096*
C10	0.1397 (3)	0.62815 (15)	0.0796 (2)	0.0822 (8)
H10	0.1204	0.6708	0.0331	0.099*
C11	0.2772 (3)	0.60493 (13)	0.14280 (19)	0.0631 (6)
H11	0.3501	0.6319	0.1383	0.076*
C12	0.4517 (7)	0.3942 (4)	0.1774 (6)	0.0362 (12)	0.50
C13	0.4027 (10)	0.3246 (6)	0.1945 (5)	0.0663 (7)	0.50
H13	0.4246	0.3081	0.2690	0.080*	0.50
C14	0.3208 (9)	0.2798 (4)	0.1002 (8)	0.0720 (15)	0.50
H14	0.2880	0.2333	0.1116	0.086*	0.50
C15	0.2879 (7)	0.3045 (4)	−0.0112 (6)	0.0686 (16)	0.50
H15	0.2331	0.2745	−0.0742	0.082*	0.50
C16	0.3369 (10)	0.3741 (6)	−0.0283 (5)	0.0685 (10)	0.50
C17	0.4188 (8)	0.4189 (4)	0.0660 (8)	0.0459 (12)	0.50
H17	0.4516	0.4654	0.0545	0.055*	0.50
C18	0.2992 (15)	0.3922 (5)	−0.1542 (5)	0.1145 (12)	0.50
H18A	0.2297	0.4315	−0.1807	0.172*	0.50
H18B	0.2623	0.3478	−0.2005	0.172*	0.50
H18C	0.3819	0.4087	−0.1608	0.172*	0.50
C12'	0.4183 (7)	0.4036 (4)	0.1680 (6)	0.0362 (12)	0.50
C13'	0.4065 (10)	0.3301 (6)	0.2006 (4)	0.0663 (7)	0.50
H13'	0.4309	0.3190	0.2776	0.080*	0.50
C14'	0.3584 (9)	0.2731 (4)	0.1180 (8)	0.0720 (15)	0.50
H14'	0.3505	0.2239	0.1398	0.086*	0.50
C15'	0.3219 (8)	0.2897 (4)	0.0029 (6)	0.0686 (16)	0.50
H15'	0.2897	0.2516	−0.0524	0.082*	0.50
C16'	0.3337 (10)	0.3633 (6)	−0.0297 (4)	0.0685 (10)	0.50
C17'	0.3819 (8)	0.4203 (4)	0.0529 (8)	0.0459 (12)	0.50
H17'	0.3898	0.4695	0.0312	0.055*	0.50
C18'	0.2985 (14)	0.3918 (2)	−0.1529 (2)	0.1145 (12)	0.50
H18D	0.2052	0.3758	−0.2049	0.172*	0.50
H18E	0.3648	0.3712	−0.1776	0.172*	0.50
H18F	0.3034	0.4459	−0.1527	0.172*	0.50
C19	0.59640 (16)	0.70713 (9)	0.38558 (12)	0.0420 (4)
C20	0.73709 (16)	0.72002 (10)	0.41591 (12)	0.0567 (5)
H20	0.8059	0.6889	0.4690	0.068*
C21	0.7737 (3)	0.78024 (14)	0.3657 (2)	0.0777 (7)
H21	0.8679	0.7898	0.3853	0.093*
C22	0.6707 (4)	0.82612 (15)	0.2866 (2)	0.0850 (9)
H22	0.6961	0.8661	0.2527	0.102*
C23	0.5320 (3)	0.81318 (13)	0.2580 (2)	0.0755 (7)
H23	0.4634	0.8446	0.2054	0.091*
C24	0.4932 (2)	0.75312 (11)	0.30731 (17)	0.0562 (5)
H24	0.3989	0.7440	0.2878	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0528 (3)	0.0324 (2)	0.0414 (3)	0.00075 (18)	0.0268 (2)	−0.00099 (17)
O1	0.0550 (9)	0.0472 (8)	0.0739 (10)	0.0037 (6)	0.0399 (8)	−0.0035 (7)
O2	0.0773 (10)	0.0465 (8)	0.0364 (7)	0.0045 (7)	0.0249 (7)	−0.0011 (5)
O3	0.0572 (10)	0.0547 (9)	0.0710 (10)	−0.0084 (7)	0.0205 (8)	−0.0132 (7)
N1	0.0500 (10)	0.0366 (8)	0.0474 (8)	−0.0036 (6)	0.0232 (8)	−0.0090 (6)
N2	0.0470 (9)	0.0415 (9)	0.0519 (9)	−0.0001 (7)	0.0239 (8)	−0.0062 (7)
C1	0.0521 (13)	0.0565 (13)	0.0761 (15)	0.0077 (10)	0.0259 (12)	0.0102 (11)
C2	0.0464 (11)	0.0466 (11)	0.0486 (10)	−0.0017 (8)	0.0264 (9)	−0.0043 (8)
C3	0.0470 (11)	0.0337 (9)	0.0464 (10)	−0.0019 (7)	0.0256 (9)	−0.0020 (7)
C4	0.0474 (10)	0.0319 (9)	0.0406 (9)	−0.0021 (7)	0.0242 (8)	−0.0010 (7)
C5	0.0473 (11)	0.0333 (9)	0.0408 (9)	−0.0027 (7)	0.0238 (8)	−0.0008 (7)
C6	0.0495 (11)	0.0381 (10)	0.0404 (9)	−0.0004 (8)	0.0184 (9)	−0.0012 (7)
C7	0.0516 (13)	0.0572 (13)	0.0562 (12)	0.0001 (9)	0.0234 (11)	0.0081 (9)
C8	0.0483 (14)	0.0915 (18)	0.0703 (15)	0.0003 (12)	0.0199 (12)	0.0094 (13)
C9	0.0616 (17)	0.091 (2)	0.0703 (16)	0.0187 (14)	0.0123 (13)	0.0107 (14)
C10	0.084 (2)	0.0708 (17)	0.0720 (16)	0.0151 (14)	0.0159 (15)	0.0280 (13)
C11	0.0649 (15)	0.0553 (13)	0.0619 (13)	−0.0018 (11)	0.0211 (12)	0.0165 (10)
C12	0.022 (3)	0.0355 (19)	0.0547 (14)	0.007 (2)	0.0206 (17)	−0.0108 (14)
C13	0.0873 (18)	0.0454 (16)	0.0844 (16)	−0.0160 (12)	0.0545 (15)	−0.0206 (12)
C14	0.063 (4)	0.0491 (16)	0.117 (3)	−0.016 (2)	0.051 (3)	−0.0338 (17)
C15	0.037 (4)	0.072 (3)	0.092 (2)	0.001 (3)	0.023 (2)	−0.046 (2)
C16	0.0551 (15)	0.085 (3)	0.0636 (14)	−0.0097 (16)	0.0246 (12)	−0.0338 (14)
C17	0.022 (4)	0.0633 (13)	0.049 (2)	−0.0071 (17)	0.012 (2)	−0.0137 (11)
C18	0.109 (3)	0.164 (3)	0.0582 (16)	−0.006 (2)	0.0247 (17)	−0.0346 (18)
C12'	0.022 (3)	0.0355 (19)	0.0547 (14)	0.007 (2)	0.0206 (17)	−0.0108 (14)
C13'	0.0873 (18)	0.0454 (16)	0.0844 (16)	−0.0160 (12)	0.0545 (15)	−0.0206 (12)
C14'	0.063 (4)	0.0491 (16)	0.117 (3)	−0.016 (2)	0.051 (3)	−0.0338 (17)
C15'	0.037 (4)	0.072 (3)	0.092 (2)	0.001 (3)	0.023 (2)	−0.046 (2)
C16'	0.0551 (15)	0.085 (3)	0.0636 (14)	−0.0097 (16)	0.0246 (12)	−0.0338 (14)
C17'	0.022 (4)	0.0633 (13)	0.049 (2)	−0.0071 (17)	0.012 (2)	−0.0137 (11)
C18'	0.109 (3)	0.164 (3)	0.0582 (16)	−0.006 (2)	0.0247 (17)	−0.0346 (18)
C19	0.0583 (12)	0.0319 (9)	0.0389 (9)	−0.0036 (8)	0.0241 (9)	−0.0048 (7)
C20	0.0614 (14)	0.0467 (11)	0.0677 (13)	−0.0072 (9)	0.0333 (11)	−0.0009 (10)
C21	0.0881 (19)	0.0641 (16)	0.0975 (19)	−0.0226 (14)	0.0560 (17)	−0.0040 (14)
C22	0.134 (3)	0.0551 (15)	0.0825 (18)	−0.0239 (16)	0.0628 (19)	0.0065 (13)
C23	0.112 (2)	0.0456 (13)	0.0597 (14)	−0.0017 (13)	0.0294 (15)	0.0126 (10)
C24	0.0689 (14)	0.0422 (11)	0.0514 (11)	0.0000 (9)	0.0208 (11)	0.0041 (9)

Geometric parameters (Å, º) top

S1—O1	1.4316 (14)	C14—H14	0.9300
S1—O2	1.4314 (14)	C15—C16	1.3900
S1—C4	1.7554 (17)	C15—H15	0.9300
S1—C19	1.7713 (15)	C16—C17	1.3900
O3—C2	1.211 (2)	C16—C18	1.525 (6)
N1—N2	1.358 (2)	C17—H17	0.9300
N1—C5	1.361 (2)	C18—H18A	0.9600
N1—C12	1.434 (5)	C18—H18B	0.9600
N1—C12'	1.450 (5)	C18—H18C	0.9600
N2—C3	1.332 (2)	C12'—C13'	1.3900
C1—C2	1.495 (3)	C12'—C17'	1.3900
C1—H1A	0.9600	C13'—C14'	1.3900
C1—H1B	0.9600	C13'—H13'	0.9300
C1—H1C	0.9600	C14'—C15'	1.3900
C2—C3	1.484 (3)	C14'—H14'	0.9300
C3—C4	1.426 (2)	C15'—C16'	1.3900
C4—C5	1.390 (2)	C15'—H15'	0.9300
C5—C6	1.469 (3)	C16'—C17'	1.3900
C6—C11	1.380 (3)	C16'—C18'	1.547 (5)
C6—C7	1.387 (3)	C17'—H17'	0.9300
C7—C8	1.385 (3)	C18'—H18D	0.9600
C7—H7	0.9300	C18'—H18E	0.9600
C8—C9	1.367 (4)	C18'—H18F	0.9600
C8—H8	0.9300	C19—C24	1.381 (2)
C9—C10	1.368 (4)	C19—C20	1.382 (3)
C9—H9	0.9300	C20—C21	1.387 (3)
C10—C11	1.381 (3)	C20—H20	0.9300
C10—H10	0.9300	C21—C22	1.382 (4)
C11—H11	0.9300	C21—H21	0.9300
C12—C13	1.3900	C22—C23	1.366 (4)
C12—C17	1.3900	C22—H22	0.9300
C13—C14	1.3900	C23—C24	1.389 (3)
C13—H13	0.9300	C23—H23	0.9300
C14—C15	1.3900	C24—H24	0.9300

O1—S1—O2	118.81 (9)	C13—C14—C15	120.0
O1—S1—C4	107.23 (8)	C13—C14—H14	120.0
O2—S1—C4	108.48 (8)	C15—C14—H14	120.0
O1—S1—C19	107.36 (8)	C16—C15—C14	120.0
O2—S1—C19	108.37 (8)	C16—C15—H15	120.0
C4—S1—C19	105.89 (7)	C14—C15—H15	120.0
N2—N1—C5	113.22 (14)	C15—C16—C17	120.0
N2—N1—C12	111.9 (3)	C15—C16—C18	114.4 (7)
C5—N1—C12	134.9 (3)	C17—C16—C18	125.6 (7)
N2—N1—C12'	126.1 (3)	C16—C17—C12	120.0
C5—N1—C12'	120.7 (3)	C16—C17—H17	120.0
C3—N2—N1	105.36 (14)	C12—C17—H17	120.0
C2—C1—H1A	109.5	C13'—C12'—C17'	120.0
C2—C1—H1B	109.5	C13'—C12'—N1	113.7 (7)
H1A—C1—H1B	109.5	C17'—C12'—N1	124.2 (7)
C2—C1—H1C	109.5	C12'—C13'—C14'	120.0
H1A—C1—H1C	109.5	C12'—C13'—H13'	120.0
H1B—C1—H1C	109.5	C14'—C13'—H13'	120.0
O3—C2—C3	121.22 (18)	C13'—C14'—C15'	120.0
O3—C2—C1	122.0 (2)	C13'—C14'—H14'	120.0
C3—C2—C1	116.76 (17)	C15'—C14'—H14'	120.0
N2—C3—C4	110.24 (16)	C14'—C15'—C16'	120.0
N2—C3—C2	117.59 (16)	C14'—C15'—H15'	120.0
C4—C3—C2	132.17 (16)	C16'—C15'—H15'	120.0
C5—C4—C3	105.91 (15)	C17'—C16'—C15'	120.0
C5—C4—S1	124.43 (14)	C17'—C16'—C18'	113.1 (7)
C3—C4—S1	129.29 (14)	C15'—C16'—C18'	126.9 (7)
N1—C5—C4	105.25 (16)	C16'—C17'—C12'	120.0
N1—C5—C6	122.09 (16)	C16'—C17'—H17'	120.0
C4—C5—C6	132.64 (16)	C12'—C17'—H17'	120.0
C11—C6—C7	119.18 (19)	C16'—C18'—H18D	109.5
C11—C6—C5	121.16 (18)	C16'—C18'—H18E	109.5
C7—C6—C5	119.66 (16)	H18D—C18'—H18E	109.5
C8—C7—C6	119.9 (2)	C16'—C18'—H18F	109.5
C8—C7—H7	120.0	H18D—C18'—H18F	109.5
C6—C7—H7	120.0	H18E—C18'—H18F	109.5
C9—C8—C7	120.2 (2)	C24—C19—C20	121.21 (13)
C9—C8—H8	119.9	C24—C19—S1	119.32 (14)
C7—C8—H8	119.9	C20—C19—S1	119.46 (6)
C8—C9—C10	120.2 (2)	C19—C20—C21	118.73 (15)
C8—C9—H9	119.9	C19—C20—H20	120.6
C10—C9—H9	119.9	C21—C20—H20	120.6
C9—C10—C11	120.2 (2)	C22—C21—C20	120.3 (2)
C9—C10—H10	119.9	C22—C21—H21	119.8
C11—C10—H10	119.9	C20—C21—H21	119.8
C6—C11—C10	120.3 (2)	C23—C22—C21	120.4 (2)
C6—C11—H11	119.9	C23—C22—H22	119.8
C10—C11—H11	119.9	C21—C22—H22	119.8
C13—C12—C17	120.0	C22—C23—C24	120.1 (2)
C13—C12—N1	123.6 (7)	C22—C23—H23	119.9
C17—C12—N1	114.5 (7)	C24—C23—H23	119.9
C14—C13—C12	120.0	C19—C24—C23	119.2 (2)
C14—C13—H13	120.0	C19—C24—H24	120.4
C12—C13—H13	120.0	C23—C24—H24	120.4

C5—N1—N2—C3	−1.55 (19)	N2—N1—C12—C17	−116.8 (4)
C12—N1—N2—C3	177.1 (5)	C5—N1—C12—C17	61.4 (7)
C12'—N1—N2—C3	179.6 (5)	C12'—N1—C12—C17	71 (3)
N1—N2—C3—C4	0.88 (19)	C17—C12—C13—C14	0.0
N1—N2—C3—C2	−178.29 (14)	N1—C12—C13—C14	163.3 (5)
O3—C2—C3—N2	150.22 (18)	C12—C13—C14—C15	0.0
C1—C2—C3—N2	−29.7 (2)	C13—C14—C15—C16	0.0
O3—C2—C3—C4	−28.7 (3)	C14—C15—C16—C17	0.0
C1—C2—C3—C4	151.39 (19)	C14—C15—C16—C18	177.0 (10)
N2—C3—C4—C5	0.03 (19)	C15—C16—C17—C12	0.0
C2—C3—C4—C5	179.04 (18)	C18—C16—C17—C12	−176.7 (11)
N2—C3—C4—S1	173.15 (13)	C13—C12—C17—C16	0.0
C2—C3—C4—S1	−7.8 (3)	N1—C12—C17—C16	−164.8 (5)
O1—S1—C4—C5	22.34 (17)	N2—N1—C12'—C13'	54.4 (6)
O2—S1—C4—C5	151.81 (14)	C5—N1—C12'—C13'	−124.5 (3)
C19—S1—C4—C5	−92.06 (15)	C12—N1—C12'—C13'	64 (3)
O1—S1—C4—C3	−149.63 (16)	N2—N1—C12'—C17'	−108.7 (6)
O2—S1—C4—C3	−20.16 (18)	C5—N1—C12'—C17'	72.4 (6)
C19—S1—C4—C3	95.97 (16)	C12—N1—C12'—C17'	−99 (3)
N2—N1—C5—C4	1.57 (19)	C17'—C12'—C13'—C14'	0.0
C12—N1—C5—C4	−176.6 (6)	N1—C12'—C13'—C14'	−163.9 (6)
C12'—N1—C5—C4	−179.5 (5)	C12'—C13'—C14'—C15'	0.0
N2—N1—C5—C6	−176.67 (15)	C13'—C14'—C15'—C16'	0.0
C12—N1—C5—C6	5.1 (7)	C14'—C15'—C16'—C17'	0.0
C12'—N1—C5—C6	2.3 (5)	C14'—C15'—C16'—C18'	179.9 (11)
C3—C4—C5—N1	−0.93 (18)	C15'—C16'—C17'—C12'	0.0
S1—C4—C5—N1	−174.47 (12)	C18'—C16'—C17'—C12'	−179.9 (9)
C3—C4—C5—C6	177.05 (17)	C13'—C12'—C17'—C16'	0.0
S1—C4—C5—C6	3.5 (3)	N1—C12'—C17'—C16'	162.1 (6)
N1—C5—C6—C11	−113.8 (2)	O1—S1—C19—C24	−10.71 (16)
C4—C5—C6—C11	68.5 (3)	O2—S1—C19—C24	−140.20 (14)
N1—C5—C6—C7	67.2 (2)	C4—S1—C19—C24	103.59 (15)
C4—C5—C6—C7	−110.5 (2)	O1—S1—C19—C20	167.98 (11)
C11—C6—C7—C8	−0.9 (3)	O2—S1—C19—C20	38.50 (12)
C5—C6—C7—C8	178.2 (2)	C4—S1—C19—C20	−77.71 (12)
C6—C7—C8—C9	−0.6 (4)	C24—C19—C20—C21	−0.3 (2)
C7—C8—C9—C10	1.6 (4)	S1—C19—C20—C21	−178.99 (16)
C8—C9—C10—C11	−1.1 (4)	C19—C20—C21—C22	−0.2 (3)
C7—C6—C11—C10	1.4 (3)	C20—C21—C22—C23	0.7 (4)
C5—C6—C11—C10	−177.7 (2)	C21—C22—C23—C24	−0.7 (4)
C9—C10—C11—C6	−0.4 (4)	C20—C19—C24—C23	0.3 (3)
N2—N1—C12—C13	79.0 (4)	S1—C19—C24—C23	178.96 (16)
C5—N1—C12—C13	−102.8 (6)	C22—C23—C24—C19	0.2 (3)
C12'—N1—C12—C13	−93 (3)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₂O₃S
M_r	416.48
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.5717 (4), 17.7004 (6), 12.8744 (4)
β (°)	115.945 (1)
V (Å³)	2166.30 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.933, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	23603, 4951, 3490
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.131, 1.16
No. of reflections	4951
No. of parameters	266
No. of restraints	44
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.37

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the Deanship of Scientific Research of the College of Science Research Center, King Saud University, and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Nasser, E., Abdel-Aziz, H. A., Ibrahim, H. S. & Mansour, A. M. (2011). Sci. Pharm. 79, 507–524. PubMed Google Scholar
Rigaku (2007). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar