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ISSN: 2056-9890

3-(5-Phenyl-4-phenyl­sulfonyl-1-p-tolyl-1H-pyrazol-3-yl)-1,2-di­hydro­quinoxaline

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 14 February 2011; accepted 17 February 2011; online 23 February 2011)

In the crystal structure of the title compound, C30H24N4O2S, the dihydro­quinoxaline fused-ring system is disordered over three orientations in a 0.358 (2):0.318 (3):0.324 (3) ratio; the mean planes of the non-H atoms of the disorder components are aligned at 4.0 (3), 11.8 (4) and 41.7 (2)° with respect to the pyrazole ring. The rings of the phenyl and tolyl substituents are aligned at 64.0 (1) and 43.7 (1)° with respect to the pyrazole ring. Weak intermolecular C—H⋯O hydrogen bonding links the mol­ecules, forming supra­molecular chains running along the a axis.

Related literature

For background to the biological properties of aryl-substituted pyrazoles, see: Abdel-Aziz et al. (2010[Abdel-Aziz, H. A., El-Zahabi, H. S. A. & Dawood, K. M. (2010). Eur. J. Med. Chem. 45, 2427-2432.]).

[Scheme 1]

Experimental

Crystal data
  • C30H24N4O2S

  • Mr = 504.59

  • Monoclinic, P 21 /c

  • a = 6.2829 (2) Å

  • b = 24.5162 (7) Å

  • c = 15.9180 (5) Å

  • β = 91.925 (3)°

  • V = 2450.51 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 100 K

  • 0.20 × 0.02 × 0.02 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.967, Tmax = 0.997

  • 16288 measured reflections

  • 5524 independent reflections

  • 3897 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.158

  • S = 1.02

  • 5524 reflections

  • 422 parameters

  • 139 restraints

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C19—H19⋯O1i 0.95 2.57 3.430 (3) 150
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

We have reported the antitumor activity of aryl-pyrazoles against CaCo-2 and HEP-2 cell lines (Abdel-Aziz et al., 2010). These compounds were synthesized by a cycloaddition under microwave conditions. The study is now extended to the synthesis of a pyrazole having a dihydroquinoxaline substituent (Scheme I). The dihydroquinoxalinyl subsitutent of the pyrazolyl ring of C30H24N4O2S adopts three orientations. The orientations refined to a 0.358 (2): 0.318 (3): 0.324 (3) ratio. The mean planes of the atoms passing through the non-hydrogen atoms of the disorder components are aligned at 4.0 (3), 11.8 (4) and 41.7 (2)° with respect to the five-membered ring (Fig. 1).

Related literature top

For background to the biological properties of aryl-substituted pyrazoles, see: Abdel-Aziz et al. (2010).

Experimental top

The acetyl portion of 1-[5-phenyl-4-(phenylfulonyl)-1-p-tolyl-1H-pyrazol-3-yl]ethane was first converted to a bromoacetyl unit by bromination at 363–373 K to yield 2-bromo-1-[5-phenyl-4-(phenylsulfonyl)-1-p-tolyl-1H-pyrazol-3-yl)ethanone. The compound (10 mmol) was heated with o-phenylenediamine (10 mmol) in ethanol to yield the title compound. Crystals were obtained upon recrystallization from ethanol.

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 to 0.98 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation.

The dihydroquinoxalinyl fused-ring is disordered over three orientations in a 0.358 (2): 0.318 (3): 0.324 (3) ratio. The first two disorder components are close to each other, so that the temperature factors of the singly-primed atoms were set to those of the unprimed atoms. The anisotropic temperature factors of the atoms of the three disorder components were restrained to be nearly isotropic, with the restraint being much tighter for the C1/C1'/C1" set of atoms. The aromatic rings were refined as rigid hexagons of 1.39 Å sides. The carbon–nitrogentertiary distances were restrained to 1.35±0.01 Å and the carbon–nitrogensecondary to 1.45±0.01 Å. The carbon–carbon single-bond distances were restrained to 1.50±0.01 Å. The amino H-atoms were treated in the riding mode [N—H 0.88 Å, Uiso(H) 1.2Ueq(N)].

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C30H24N4O2S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
3-(5-Phenyl-4-phenylsulfonyl-1-p-tolyl-1H-pyrazol-3-yl)- 1,2-dihydroquinoxaline top
Crystal data top
C30H24N4O2SF(000) = 1056
Mr = 504.59Dx = 1.368 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4169 reflections
a = 6.2829 (2) Åθ = 2.5–29.3°
b = 24.5162 (7) ŵ = 0.17 mm1
c = 15.9180 (5) ÅT = 100 K
β = 91.925 (3)°Prism, yellow
V = 2450.51 (13) Å30.20 × 0.02 × 0.02 mm
Z = 4
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
5524 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3897 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.054
Detector resolution: 10.4041 pixels mm-1θmax = 27.5°, θmin = 2.6°
ω scansh = 88
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
k = 3131
Tmin = 0.967, Tmax = 0.997l = 2020
16288 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0634P)2 + 1.9372P]
where P = (Fo2 + 2Fc2)/3
5524 reflections(Δ/σ)max = 0.001
422 parametersΔρmax = 0.38 e Å3
139 restraintsΔρmin = 0.40 e Å3
Crystal data top
C30H24N4O2SV = 2450.51 (13) Å3
Mr = 504.59Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.2829 (2) ŵ = 0.17 mm1
b = 24.5162 (7) ÅT = 100 K
c = 15.9180 (5) Å0.20 × 0.02 × 0.02 mm
β = 91.925 (3)°
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
5524 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
3897 reflections with I > 2σ(I)
Tmin = 0.967, Tmax = 0.997Rint = 0.054
16288 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.062139 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 1.02Δρmax = 0.38 e Å3
5524 reflectionsΔρmin = 0.40 e Å3
422 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.81495 (10)0.59167 (2)0.63024 (4)0.02549 (18)
O11.0308 (3)0.59391 (8)0.66188 (15)0.0434 (6)
O20.7677 (3)0.62026 (7)0.55309 (12)0.0317 (5)
N10.804 (2)0.5182 (4)0.8067 (8)0.034 (3)0.358 (2)
N20.6304 (13)0.5044 (4)0.9751 (5)0.0518 (19)0.358 (2)
H20.58320.50241.02640.062*0.358 (2)
N1'0.854 (3)0.5300 (7)0.8110 (12)0.034 (3)0.318 (3)
N2'0.7437 (15)0.5043 (5)0.9645 (7)0.0518 (19)0.318 (3)
H2'0.69850.49161.01250.062*0.318 (3)
N1"0.8972 (12)0.5346 (4)0.7959 (8)0.018 (2)0.324 (3)
N2"0.6519 (13)0.4503 (3)0.8722 (6)0.058 (3)0.324 (3)
H2"0.57960.42440.89670.070*0.324 (3)
N30.4322 (4)0.62374 (9)0.81706 (14)0.0300 (5)
N40.3835 (3)0.66333 (8)0.76021 (13)0.0224 (5)
C10.696 (2)0.5572 (4)0.8435 (7)0.027 (2)0.358 (2)
C20.5687 (19)0.5421 (6)0.9157 (8)0.049 (3)0.358 (2)
H2A0.54180.57640.94650.059*0.358 (2)
H2B0.42900.52980.89220.059*0.358 (2)
C30.7815 (8)0.4692 (2)0.9407 (3)0.0328 (14)0.358 (2)
C40.8492 (9)0.4250 (2)0.9894 (3)0.0443 (16)0.358 (2)
H4A0.79230.41941.04330.053*0.358 (2)
C51.0001 (10)0.3892 (2)0.9594 (3)0.0458 (17)0.358 (2)
H51.04640.35900.99270.055*0.358 (2)
C61.0834 (10)0.3974 (2)0.8806 (4)0.054 (2)0.358 (2)
H61.18650.37290.86000.065*0.358 (2)
C71.0157 (10)0.4416 (2)0.8318 (3)0.0432 (18)0.358 (2)
H71.07260.44720.77800.052*0.358 (2)
C80.8647 (9)0.47745 (19)0.8619 (3)0.0314 (16)0.358 (2)
C1'0.659 (2)0.5469 (5)0.8348 (9)0.027 (2)0.318 (3)
C2'0.634 (2)0.5474 (6)0.9271 (9)0.049 (3)0.318 (3)
H2'A0.68850.58220.95060.059*0.318 (3)
H2'B0.48090.54460.93960.059*0.318 (3)
C3'0.9213 (9)0.4799 (2)0.9307 (4)0.0328 (14)0.318 (3)
C4'1.0383 (11)0.4432 (3)0.9802 (3)0.0443 (16)0.318 (3)
H4'0.99690.43561.03580.053*0.318 (3)
C5'1.2157 (10)0.4176 (3)0.9483 (4)0.0458 (17)0.318 (3)
H5'1.29570.39250.98210.055*0.318 (3)
C6'1.2763 (11)0.4288 (3)0.8669 (4)0.054 (2)0.318 (3)
H6'1.39760.41130.84510.065*0.318 (3)
C7'1.1594 (14)0.4655 (4)0.8174 (3)0.0432 (18)0.318 (3)
H7'1.20070.47310.76170.052*0.318 (3)
C8'0.9819 (12)0.4911 (3)0.8493 (4)0.0314 (16)0.318 (3)
C1"0.6918 (14)0.5421 (4)0.8112 (7)0.030 (3)0.324 (3)
C2"0.5589 (15)0.4998 (3)0.8485 (6)0.042 (2)0.324 (3)
H2"A0.49480.51570.89890.050*0.324 (3)
H2"B0.44060.49170.80780.050*0.324 (3)
C3"0.8676 (10)0.4445 (3)0.8547 (5)0.053 (3)0.324 (3)
C4"0.9628 (12)0.3945 (3)0.8730 (6)0.065 (4)0.324 (3)
H4"0.88160.36590.89620.078*0.324 (3)
C5"1.1768 (13)0.3865 (3)0.8573 (6)0.075 (4)0.324 (3)
H5"1.24190.35230.86980.089*0.324 (3)
C6"1.2956 (10)0.4284 (3)0.8234 (6)0.065 (4)0.324 (3)
H6"1.44190.42290.81260.078*0.324 (3)
C7"1.2003 (12)0.4783 (3)0.8051 (5)0.051 (3)0.324 (3)
H7"1.28150.50700.78190.061*0.324 (3)
C8"0.9863 (12)0.4864 (2)0.8208 (5)0.044 (3)0.324 (3)
C90.5873 (4)0.59504 (10)0.78359 (17)0.0275 (6)
C100.6366 (4)0.61620 (9)0.70379 (16)0.0213 (5)
C110.5021 (4)0.66014 (9)0.69050 (15)0.0193 (5)
C120.7410 (4)0.52265 (10)0.61533 (16)0.0222 (5)
C130.9002 (4)0.48606 (10)0.59728 (18)0.0306 (6)
H131.04490.49740.59860.037*
C140.8469 (4)0.43271 (11)0.57721 (18)0.0313 (6)
H140.95540.40750.56370.038*
C150.6385 (4)0.41603 (10)0.57666 (17)0.0279 (6)
H150.60290.37930.56330.034*
C160.4805 (4)0.45288 (10)0.5956 (2)0.0336 (7)
H160.33640.44120.59600.040*
C170.5304 (4)0.50657 (10)0.61392 (18)0.0299 (6)
H170.42130.53210.62540.036*
C180.4762 (4)0.69961 (9)0.62105 (16)0.0230 (5)
C190.2844 (4)0.70325 (11)0.57537 (16)0.0279 (6)
H190.17210.67850.58600.033*
C200.2575 (5)0.74308 (13)0.51430 (19)0.0420 (8)
H200.12630.74560.48310.050*
C210.4199 (7)0.77902 (13)0.4985 (2)0.0522 (9)
H210.39980.80680.45750.063*
C220.6139 (6)0.77443 (13)0.5431 (2)0.0519 (9)
H220.72730.79860.53120.062*
C230.6420 (5)0.73508 (11)0.60416 (18)0.0352 (7)
H230.77410.73220.63470.042*
C240.2196 (4)0.70160 (11)0.77998 (16)0.0273 (6)
C250.2472 (4)0.75683 (11)0.76539 (19)0.0338 (6)
H250.37230.76980.74010.041*
C260.0889 (5)0.79293 (13)0.7884 (2)0.0409 (7)
H260.10700.83090.77900.049*
C270.0956 (4)0.77443 (13)0.8251 (2)0.0406 (8)
C280.1194 (4)0.71885 (13)0.83758 (19)0.0383 (7)
H280.24540.70570.86200.046*
C290.0362 (4)0.68207 (12)0.81537 (17)0.0310 (6)
H290.01740.64410.82420.037*
C300.2606 (5)0.81477 (15)0.8538 (2)0.0539 (10)
H30A0.39790.79620.85850.081*
H30B0.27500.84450.81290.081*
H30C0.21570.82970.90870.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0197 (3)0.0221 (3)0.0349 (4)0.0019 (2)0.0043 (3)0.0087 (3)
O10.0207 (9)0.0356 (11)0.0736 (16)0.0014 (8)0.0025 (10)0.0245 (11)
O20.0408 (11)0.0249 (9)0.0305 (10)0.0031 (8)0.0153 (9)0.0025 (8)
N10.061 (6)0.015 (5)0.025 (3)0.003 (4)0.019 (4)0.008 (3)
N20.062 (5)0.062 (3)0.033 (3)0.014 (5)0.013 (4)0.021 (3)
N1'0.061 (6)0.015 (5)0.025 (3)0.003 (4)0.019 (4)0.008 (3)
N2'0.062 (5)0.062 (3)0.033 (3)0.014 (5)0.013 (4)0.021 (3)
N1"0.017 (3)0.021 (4)0.018 (4)0.001 (3)0.011 (3)0.007 (3)
N2"0.081 (6)0.034 (4)0.062 (6)0.000 (4)0.027 (5)0.017 (4)
N30.0298 (12)0.0392 (13)0.0211 (11)0.0052 (10)0.0004 (9)0.0040 (10)
N40.0209 (10)0.0268 (10)0.0193 (10)0.0008 (8)0.0009 (8)0.0030 (9)
C10.044 (4)0.017 (4)0.021 (3)0.011 (3)0.014 (3)0.003 (3)
C20.068 (7)0.044 (4)0.033 (4)0.022 (4)0.033 (4)0.010 (3)
C30.041 (3)0.031 (3)0.026 (3)0.008 (3)0.004 (3)0.007 (2)
C40.052 (4)0.041 (3)0.040 (3)0.010 (3)0.003 (3)0.007 (3)
C50.054 (4)0.037 (3)0.045 (4)0.013 (3)0.006 (3)0.013 (3)
C60.055 (5)0.048 (4)0.058 (5)0.028 (4)0.005 (4)0.006 (4)
C70.049 (4)0.042 (4)0.039 (4)0.022 (3)0.006 (4)0.009 (3)
C80.031 (4)0.026 (3)0.038 (4)0.002 (3)0.002 (3)0.002 (3)
C1'0.044 (4)0.017 (4)0.021 (3)0.011 (3)0.014 (3)0.003 (3)
C2'0.068 (7)0.044 (4)0.033 (4)0.022 (4)0.033 (4)0.010 (3)
C3'0.041 (3)0.031 (3)0.026 (3)0.008 (3)0.004 (3)0.007 (2)
C4'0.052 (4)0.041 (3)0.040 (3)0.010 (3)0.003 (3)0.007 (3)
C5'0.054 (4)0.037 (3)0.045 (4)0.013 (3)0.006 (3)0.013 (3)
C6'0.055 (5)0.048 (4)0.058 (5)0.028 (4)0.005 (4)0.006 (4)
C7'0.049 (4)0.042 (4)0.039 (4)0.022 (3)0.006 (4)0.009 (3)
C8'0.031 (4)0.026 (3)0.038 (4)0.002 (3)0.002 (3)0.002 (3)
C1"0.040 (4)0.033 (5)0.017 (4)0.002 (4)0.006 (4)0.009 (4)
C2"0.055 (5)0.029 (4)0.042 (5)0.003 (4)0.012 (4)0.000 (4)
C3"0.064 (6)0.056 (6)0.041 (5)0.014 (5)0.018 (5)0.011 (5)
C4"0.087 (8)0.053 (6)0.057 (6)0.026 (6)0.008 (6)0.014 (5)
C5"0.088 (8)0.062 (7)0.076 (7)0.030 (6)0.022 (6)0.012 (6)
C6"0.071 (7)0.067 (7)0.056 (7)0.024 (6)0.001 (6)0.012 (6)
C7"0.049 (6)0.050 (6)0.054 (6)0.023 (5)0.001 (5)0.000 (5)
C8"0.058 (6)0.042 (6)0.033 (5)0.017 (5)0.003 (5)0.009 (5)
C90.0296 (13)0.0253 (13)0.0274 (14)0.0026 (11)0.0031 (11)0.0049 (11)
C100.0210 (12)0.0188 (11)0.0240 (13)0.0009 (9)0.0013 (10)0.0032 (10)
C110.0178 (11)0.0213 (11)0.0186 (12)0.0043 (9)0.0001 (9)0.0045 (10)
C120.0223 (12)0.0224 (12)0.0220 (13)0.0006 (10)0.0002 (10)0.0041 (10)
C130.0193 (12)0.0294 (13)0.0431 (17)0.0014 (10)0.0017 (12)0.0059 (12)
C140.0283 (14)0.0254 (13)0.0406 (16)0.0070 (11)0.0065 (12)0.0037 (12)
C150.0324 (14)0.0199 (12)0.0317 (15)0.0008 (10)0.0049 (12)0.0048 (11)
C160.0223 (13)0.0262 (13)0.0528 (19)0.0042 (11)0.0066 (13)0.0061 (13)
C170.0197 (12)0.0225 (12)0.0477 (17)0.0029 (10)0.0034 (12)0.0058 (12)
C180.0301 (13)0.0190 (11)0.0200 (13)0.0008 (10)0.0009 (10)0.0017 (10)
C190.0293 (13)0.0302 (13)0.0241 (14)0.0045 (11)0.0007 (11)0.0040 (11)
C200.0542 (19)0.0457 (18)0.0258 (15)0.0225 (16)0.0046 (14)0.0014 (14)
C210.094 (3)0.0345 (17)0.0286 (17)0.0108 (18)0.0036 (18)0.0107 (14)
C220.083 (3)0.0366 (17)0.0364 (18)0.0200 (17)0.0049 (18)0.0102 (15)
C230.0440 (17)0.0307 (14)0.0307 (15)0.0110 (13)0.0007 (13)0.0031 (12)
C240.0213 (12)0.0349 (14)0.0257 (14)0.0010 (11)0.0010 (10)0.0155 (12)
C250.0258 (13)0.0356 (15)0.0403 (16)0.0025 (12)0.0038 (12)0.0164 (13)
C260.0339 (15)0.0380 (16)0.0503 (19)0.0039 (13)0.0052 (14)0.0230 (15)
C270.0241 (14)0.0551 (19)0.0420 (18)0.0051 (13)0.0048 (12)0.0297 (15)
C280.0223 (13)0.060 (2)0.0330 (16)0.0050 (13)0.0014 (12)0.0234 (15)
C290.0223 (13)0.0443 (16)0.0261 (14)0.0013 (12)0.0025 (11)0.0129 (13)
C300.0335 (16)0.064 (2)0.064 (2)0.0130 (15)0.0042 (16)0.0388 (19)
Geometric parameters (Å, º) top
S1—O11.432 (2)C1"—C91.512 (8)
S1—O21.436 (2)C2"—H2"A0.9900
S1—C101.754 (2)C2"—H2"B0.9900
S1—C121.769 (2)C3"—C4"1.3900
N1—C11.322 (9)C3"—C8"1.3900
N1—C81.375 (9)C4"—C5"1.3900
N2—C21.370 (9)C4"—H4"0.9500
N2—C31.408 (7)C5"—C6"1.3900
N2—N2i1.856 (16)C5"—H5"0.9500
N2—H20.8800C6"—C7"1.3900
N1'—C1'1.358 (10)C6"—H6"0.9500
N1'—C8'1.379 (9)C7"—C8"1.3900
N2'—C2'1.385 (9)C7"—H7"0.9500
N2'—C3'1.390 (8)C9—C101.416 (4)
N2'—H2'0.8800C10—C111.381 (3)
N1"—C1"1.335 (8)C11—C181.474 (3)
N1"—C8"1.361 (8)C12—C131.381 (3)
N2"—C2"1.392 (8)C12—C171.380 (3)
N2"—C3"1.400 (8)C13—C141.385 (4)
N2"—H2"0.8800C13—H130.9500
N3—C91.328 (3)C14—C151.371 (4)
N3—N41.355 (3)C14—H140.9500
N4—C111.359 (3)C15—C161.383 (4)
N4—C241.436 (3)C15—H150.9500
C1—C21.469 (9)C16—C171.382 (4)
C1—C91.480 (8)C16—H160.9500
C2—H2A0.9900C17—H170.9500
C2—H2B0.9900C18—C191.389 (4)
C3—C41.3900C18—C231.390 (4)
C3—C81.3900C19—C201.384 (4)
C4—C51.3900C19—H190.9500
C4—H4A0.9500C20—C211.378 (5)
C5—C61.3900C20—H200.9500
C5—H50.9500C21—C221.394 (5)
C6—C71.3900C21—H210.9500
C6—H60.9500C22—C231.377 (4)
C7—C81.3900C22—H220.9500
C7—H70.9500C23—H230.9500
C1'—C2'1.483 (10)C24—C291.385 (4)
C1'—C91.494 (9)C24—C251.386 (4)
C2'—H2'A0.9900C25—C261.390 (4)
C2'—H2'B0.9900C25—H250.9500
C3'—C4'1.3900C26—C271.391 (4)
C3'—C8'1.3900C26—H260.9500
C4'—C5'1.3900C27—C281.386 (5)
C4'—H4'0.9500C27—C301.515 (4)
C5'—C6'1.3900C28—C291.384 (4)
C5'—H5'0.9500C28—H280.9500
C6'—C7'1.3900C29—H290.9500
C6'—H6'0.9500C30—H30A0.9800
C7'—C8'1.3900C30—H30B0.9800
C7'—H7'0.9500C30—H30C0.9800
C1"—C2"1.470 (9)
O1—S1—O2116.63 (13)C8"—C3"—N2"122.5 (6)
O1—S1—C10111.78 (12)C5"—C4"—C3"120.0
O2—S1—C10106.57 (11)C5"—C4"—H4"120.0
O1—S1—C12108.98 (12)C3"—C4"—H4"120.0
O2—S1—C12107.84 (11)C4"—C5"—C6"120.0
C10—S1—C12104.29 (12)C4"—C5"—H5"120.0
C1—N1—C8112.2 (10)C6"—C5"—H5"120.0
C2—N2—C3108.9 (9)C7"—C6"—C5"120.0
C2—N2—N2i98.0 (8)C7"—C6"—H6"120.0
C3—N2—N2i135.4 (9)C5"—C6"—H6"120.0
C2—N2—H2125.5C8"—C7"—C6"120.0
C3—N2—H2125.5C8"—C7"—H7"120.0
C1'—N1'—C8'127.4 (13)C6"—C7"—H7"120.0
C2'—N2'—C3'123.8 (10)N1"—C8"—C7"117.5 (6)
C2'—N2'—H2'118.1N1"—C8"—C3"122.3 (6)
C3'—N2'—H2'118.1C7"—C8"—C3"120.0
C1"—N1"—C8"117.2 (7)N3—C9—C10110.6 (2)
C2"—N2"—C3"115.8 (7)N3—C9—C1113.7 (6)
C2"—N2"—H2"122.1C10—C9—C1134.2 (6)
C3"—N2"—H2"122.1N3—C9—C1'114.3 (7)
C9—N3—N4105.3 (2)C10—C9—C1'135.1 (7)
N3—N4—C11112.7 (2)N3—C9—C1"130.9 (4)
N3—N4—C24118.0 (2)C10—C9—C1"118.0 (4)
C11—N4—C24129.3 (2)C11—C10—C9105.8 (2)
N1—C1—C2117.8 (10)C11—C10—S1124.51 (19)
N1—C1—C9113.7 (8)C9—C10—S1129.57 (19)
C2—C1—C9114.3 (8)N4—C11—C10105.6 (2)
N2—C2—C1124.2 (11)N4—C11—C18121.6 (2)
N2—C2—H2A106.3C10—C11—C18132.7 (2)
C1—C2—H2A106.3C13—C12—C17120.8 (2)
N2—C2—H2B106.3C13—C12—S1117.43 (19)
C1—C2—H2B106.3C17—C12—S1121.52 (19)
H2A—C2—H2B106.4C12—C13—C14119.3 (2)
C4—C3—C8120.0C12—C13—H13120.3
C4—C3—N2117.2 (5)C14—C13—H13120.3
C8—C3—N2122.8 (5)C15—C14—C13120.5 (2)
C5—C4—C3120.0C15—C14—H14119.8
C5—C4—H4A120.0C13—C14—H14119.8
C3—C4—H4A120.0C14—C15—C16119.7 (2)
C4—C5—C6120.0C14—C15—H15120.1
C4—C5—H5120.0C16—C15—H15120.1
C6—C5—H5120.0C15—C16—C17120.6 (2)
C7—C6—C5120.0C15—C16—H16119.7
C7—C6—H6120.0C17—C16—H16119.7
C5—C6—H6120.0C12—C17—C16119.1 (2)
C6—C7—C8120.0C12—C17—H17120.5
C6—C7—H7120.0C16—C17—H17120.5
C8—C7—H7120.0C19—C18—C23120.1 (2)
N1—C8—C7114.6 (7)C19—C18—C11120.5 (2)
N1—C8—C3125.3 (7)C23—C18—C11119.4 (2)
C7—C8—C3120.0C20—C19—C18119.8 (3)
N1'—C1'—C2'113.9 (12)C20—C19—H19120.1
N1'—C1'—C9110.2 (9)C18—C19—H19120.1
C2'—C1'—C9119.7 (10)C21—C20—C19120.4 (3)
N2'—C2'—C1'110.7 (11)C21—C20—H20119.8
N2'—C2'—H2'A109.5C19—C20—H20119.8
C1'—C2'—H2'A109.5C20—C21—C22119.8 (3)
N2'—C2'—H2'B109.5C20—C21—H21120.1
C1'—C2'—H2'B109.5C22—C21—H21120.1
H2'A—C2'—H2'B108.1C23—C22—C21120.3 (3)
C4'—C3'—C8'120.0C23—C22—H22119.8
C4'—C3'—N2'118.3 (6)C21—C22—H22119.8
C8'—C3'—N2'121.7 (6)C22—C23—C18119.7 (3)
C3'—C4'—C5'120.0C22—C23—H23120.1
C3'—C4'—H4'120.0C18—C23—H23120.1
C5'—C4'—H4'120.0C29—C24—C25121.1 (2)
C4'—C5'—C6'120.0C29—C24—N4118.4 (2)
C4'—C5'—H5'120.0C25—C24—N4120.4 (2)
C6'—C5'—H5'120.0C24—C25—C26118.9 (3)
C7'—C6'—C5'120.0C24—C25—H25120.6
C7'—C6'—H6'120.0C26—C25—H25120.6
C5'—C6'—H6'120.0C25—C26—C27121.1 (3)
C6'—C7'—C8'120.0C25—C26—H26119.4
C6'—C7'—H7'120.0C27—C26—H26119.4
C8'—C7'—H7'120.0C28—C27—C26118.4 (3)
N1'—C8'—C7'128.0 (9)C28—C27—C30121.4 (3)
N1'—C8'—C3'112.0 (9)C26—C27—C30120.1 (3)
C7'—C8'—C3'120.0C29—C28—C27121.6 (3)
N1"—C1"—C2"122.8 (7)C29—C28—H28119.2
N1"—C1"—C9118.6 (7)C27—C28—H28119.2
C2"—C1"—C9118.5 (7)C24—C29—C28118.9 (3)
N2"—C2"—C1"119.1 (8)C24—C29—H29120.6
N2"—C2"—H2"A107.5C28—C29—H29120.6
C1"—C2"—H2"A107.5C27—C30—H30A109.5
N2"—C2"—H2"B107.5C27—C30—H30B109.5
C1"—C2"—H2"B107.5H30A—C30—H30B109.5
H2"A—C2"—H2"B107.0C27—C30—H30C109.5
C4"—C3"—C8"120.0H30A—C30—H30C109.5
C4"—C3"—N2"117.5 (6)H30B—C30—H30C109.5
C9—N3—N4—C110.9 (3)C2'—C1'—C9—N326.6 (14)
C9—N3—N4—C24179.4 (2)N1'—C1'—C9—C1023.1 (17)
C8—N1—C1—C229.4 (15)C2'—C1'—C9—C10158.1 (8)
C8—N1—C1—C9167.0 (9)N1'—C1'—C9—C171 (4)
C3—N2—C2—C122.3 (15)C2'—C1'—C9—C164 (4)
N2i—N2—C2—C1166.2 (11)N1'—C1'—C9—C1"32 (2)
N1—C1—C2—N237.2 (17)C2'—C1'—C9—C1"167 (4)
C9—C1—C2—N2174.5 (10)N1"—C1"—C9—N3147.6 (10)
C2—N2—C3—C4174.5 (7)C2"—C1"—C9—N336.5 (13)
N2i—N2—C3—C450.6 (14)N1"—C1"—C9—C1041.6 (14)
C2—N2—C3—C86.3 (11)C2"—C1"—C9—C10134.3 (8)
N2i—N2—C3—C8130.2 (11)N1"—C1"—C9—C196 (2)
C8—C3—C4—C50.0C2"—C1"—C9—C187.9 (17)
N2—C3—C4—C5179.2 (7)N1"—C1"—C9—C1'132 (3)
C3—C4—C5—C60.0C2"—C1"—C9—C1'53 (2)
C4—C5—C6—C70.0N3—C9—C10—C110.3 (3)
C5—C6—C7—C80.0C1—C9—C10—C11164.4 (7)
C1—N1—C8—C7167.1 (8)C1'—C9—C10—C11175.7 (9)
C1—N1—C8—C315.5 (14)C1"—C9—C10—C11172.9 (5)
C6—C7—C8—N1177.5 (8)N3—C9—C10—S1175.66 (19)
C6—C7—C8—C30.0C1—C9—C10—S119.6 (7)
C4—C3—C8—N1177.3 (8)C1'—C9—C10—S10.3 (9)
N2—C3—C8—N13.6 (10)C1"—C9—C10—S13.1 (6)
C4—C3—C8—C70.0O1—S1—C10—C11119.9 (2)
N2—C3—C8—C7179.2 (7)O2—S1—C10—C118.6 (2)
C8'—N1'—C1'—C2'34 (3)C12—S1—C10—C11122.5 (2)
C8'—N1'—C1'—C9172.2 (17)O1—S1—C10—C964.8 (3)
C3'—N2'—C2'—C1'26.5 (18)O2—S1—C10—C9166.7 (2)
N1'—C1'—C2'—N2'35.5 (18)C12—S1—C10—C952.8 (3)
C9—C1'—C2'—N2'169.0 (11)N3—N4—C11—C100.7 (3)
C2'—N2'—C3'—C4'169.7 (10)C24—N4—C11—C10179.7 (2)
C2'—N2'—C3'—C8'10.8 (16)N3—N4—C11—C18179.4 (2)
C8'—C3'—C4'—C5'0.0C24—N4—C11—C180.9 (4)
N2'—C3'—C4'—C5'179.4 (8)C9—C10—C11—N40.2 (3)
C3'—C4'—C5'—C6'0.0S1—C10—C11—N4176.44 (17)
C4'—C5'—C6'—C7'0.0C9—C10—C11—C18178.8 (2)
C5'—C6'—C7'—C8'0.0S1—C10—C11—C185.0 (4)
C1'—N1'—C8'—C7'165.9 (14)O1—S1—C12—C1328.8 (3)
C1'—N1'—C8'—C3'17 (2)O2—S1—C12—C1398.7 (2)
C6'—C7'—C8'—N1'176.9 (14)C10—S1—C12—C13148.3 (2)
C6'—C7'—C8'—C3'0.0O1—S1—C12—C17157.2 (2)
C4'—C3'—C8'—N1'177.4 (12)O2—S1—C12—C1775.4 (2)
N2'—C3'—C8'—N1'3.2 (13)C10—S1—C12—C1737.7 (3)
C4'—C3'—C8'—C7'0.0C17—C12—C13—C140.3 (4)
N2'—C3'—C8'—C7'179.4 (9)S1—C12—C13—C14173.9 (2)
C8"—N1"—C1"—C2"4 (2)C12—C13—C14—C151.1 (4)
C8"—N1"—C1"—C9179.4 (10)C13—C14—C15—C160.5 (4)
C3"—N2"—C2"—C1"2.6 (15)C14—C15—C16—C170.9 (4)
N1"—C1"—C2"—N2"2.7 (18)C13—C12—C17—C161.2 (4)
C9—C1"—C2"—N2"178.4 (9)S1—C12—C17—C16175.0 (2)
C2"—N2"—C3"—C4"176.3 (7)C15—C16—C17—C121.8 (5)
C2"—N2"—C3"—C8"3.9 (12)N4—C11—C18—C1963.1 (3)
C8"—C3"—C4"—C5"0.0C10—C11—C18—C19118.5 (3)
N2"—C3"—C4"—C5"179.7 (9)N4—C11—C18—C23113.8 (3)
C3"—C4"—C5"—C6"0.0C10—C11—C18—C2364.6 (4)
C4"—C5"—C6"—C7"0.0C23—C18—C19—C201.4 (4)
C5"—C6"—C7"—C8"0.0C11—C18—C19—C20175.5 (2)
C1"—N1"—C8"—C7"179.9 (10)C18—C19—C20—C210.1 (4)
C1"—N1"—C8"—C3"5.0 (17)C19—C20—C21—C221.4 (5)
C6"—C7"—C8"—N1"175.1 (10)C20—C21—C22—C231.7 (5)
C6"—C7"—C8"—C3"0.0C21—C22—C23—C180.4 (5)
C4"—C3"—C8"—N1"174.9 (11)C19—C18—C23—C221.2 (4)
N2"—C3"—C8"—N1"5.4 (12)C11—C18—C23—C22175.7 (3)
C4"—C3"—C8"—C7"0.0N3—N4—C24—C2942.7 (3)
N2"—C3"—C8"—C7"179.7 (9)C11—N4—C24—C29136.9 (3)
N4—N3—C9—C100.7 (3)N3—N4—C24—C25136.0 (3)
N4—N3—C9—C1167.4 (5)C11—N4—C24—C2544.4 (4)
N4—N3—C9—C1'177.1 (7)C29—C24—C25—C261.3 (4)
N4—N3—C9—C1"172.0 (6)N4—C24—C25—C26177.4 (2)
N1—C1—C9—N3161.6 (8)C24—C25—C26—C270.4 (4)
C2—C1—C9—N322.5 (11)C25—C26—C27—C280.5 (5)
N1—C1—C9—C1034.1 (13)C25—C26—C27—C30176.8 (3)
C2—C1—C9—C10173.2 (7)C26—C27—C28—C290.7 (4)
N1—C1—C9—C1'66 (4)C30—C27—C28—C29176.6 (3)
C2—C1—C9—C1'73 (4)C25—C24—C29—C281.1 (4)
N1—C1—C9—C1"21.7 (12)N4—C24—C29—C28177.6 (2)
C2—C1—C9—C1"117 (2)C27—C28—C29—C240.1 (4)
N1'—C1'—C9—N3161.6 (12)
Symmetry code: (i) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···O1ii0.952.573.430 (3)150
Symmetry code: (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC30H24N4O2S
Mr504.59
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)6.2829 (2), 24.5162 (7), 15.9180 (5)
β (°) 91.925 (3)
V3)2450.51 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.20 × 0.02 × 0.02
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.967, 0.997
No. of measured, independent and
observed [I > 2σ(I)] reflections
16288, 5524, 3897
Rint0.054
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.158, 1.02
No. of reflections5524
No. of parameters422
No. of restraints139
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.40

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···O1i0.952.573.430 (3)150
Symmetry code: (i) x1, y, z.
 

Acknowledgements

We thank King Saud University and the University of Malaya for supporting this study.

References

First citationAbdel-Aziz, H. A., El-Zahabi, H. S. A. & Dawood, K. M. (2010). Eur. J. Med. Chem. 45, 2427–2432.  Web of Science CAS PubMed Google Scholar
First citationAgilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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