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

Abdel-Aziz, H.A.; Bari, A.; Ng, S.W.

doi:10.1107/S1600536811005940

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o695

doi:10.1107/S1600536811005940

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

Hatem A. Abdel-Aziz,^a Ahmed Bari ^a and Seik Weng Ng ^b ^*

^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 ).

Experimental

Crystal data

C₃₀H₂₄N₄O₂S
M_r = 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 ) T_min = 0.967, T_max = 0.997
16288 measured reflections
5524 independent reflections
3897 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536811005940/xu5163sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005940/xu5163Isup2.hkl

checkCIF report

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.

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

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

C₃₀H₂₄N₄O₂S	F(000) = 1056
M_r = 504.59	D_x = 1.368 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4169 reflections
a = 6.2829 (2) Å	θ = 2.5–29.3°
b = 24.5162 (7) Å	µ = 0.17 mm⁻¹
c = 15.9180 (5) Å	T = 100 K
β = 91.925 (3)°	Prism, yellow
V = 2450.51 (13) Å³	0.20 × 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 Source	3897 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.054
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −31→31
T_min = 0.967, T_max = 0.997	l = −20→20
16288 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0634P)² + 1.9372P] where P = (F_o² + 2F_c²)/3
5524 reflections	(Δ/σ)_max = 0.001
422 parameters	Δρ_max = 0.38 e Å⁻³
139 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₃₀H₂₄N₄O₂S	V = 2450.51 (13) Å³
M_r = 504.59	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.2829 (2) Å	µ = 0.17 mm⁻¹
b = 24.5162 (7) Å	T = 100 K
c = 15.9180 (5) Å	0.20 × 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)
T_min = 0.967, T_max = 0.997	R_int = 0.054
16288 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	139 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.02	Δρ_max = 0.38 e Å⁻³
5524 reflections	Δρ_min = −0.40 e Å⁻³
422 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.81495 (10)	0.59167 (2)	0.63024 (4)	0.02549 (18)
O1	1.0308 (3)	0.59391 (8)	0.66188 (15)	0.0434 (6)
O2	0.7677 (3)	0.62026 (7)	0.55309 (12)	0.0317 (5)
N1	0.804 (2)	0.5182 (4)	0.8067 (8)	0.034 (3)	0.358 (2)
N2	0.6304 (13)	0.5044 (4)	0.9751 (5)	0.0518 (19)	0.358 (2)
H2	0.5832	0.5024	1.0264	0.062*	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'	0.6985	0.4916	1.0125	0.062*	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"	0.5796	0.4244	0.8967	0.070*	0.324 (3)
N3	0.4322 (4)	0.62374 (9)	0.81706 (14)	0.0300 (5)
N4	0.3835 (3)	0.66333 (8)	0.76021 (13)	0.0224 (5)
C1	0.696 (2)	0.5572 (4)	0.8435 (7)	0.027 (2)	0.358 (2)
C2	0.5687 (19)	0.5421 (6)	0.9157 (8)	0.049 (3)	0.358 (2)
H2A	0.5418	0.5764	0.9465	0.059*	0.358 (2)
H2B	0.4290	0.5298	0.8922	0.059*	0.358 (2)
C3	0.7815 (8)	0.4692 (2)	0.9407 (3)	0.0328 (14)	0.358 (2)
C4	0.8492 (9)	0.4250 (2)	0.9894 (3)	0.0443 (16)	0.358 (2)
H4A	0.7923	0.4194	1.0433	0.053*	0.358 (2)
C5	1.0001 (10)	0.3892 (2)	0.9594 (3)	0.0458 (17)	0.358 (2)
H5	1.0464	0.3590	0.9927	0.055*	0.358 (2)
C6	1.0834 (10)	0.3974 (2)	0.8806 (4)	0.054 (2)	0.358 (2)
H6	1.1865	0.3729	0.8600	0.065*	0.358 (2)
C7	1.0157 (10)	0.4416 (2)	0.8318 (3)	0.0432 (18)	0.358 (2)
H7	1.0726	0.4472	0.7780	0.052*	0.358 (2)
C8	0.8647 (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'A	0.6885	0.5822	0.9506	0.059*	0.318 (3)
H2'B	0.4809	0.5446	0.9396	0.059*	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'	0.9969	0.4356	1.0358	0.053*	0.318 (3)
C5'	1.2157 (10)	0.4176 (3)	0.9483 (4)	0.0458 (17)	0.318 (3)
H5'	1.2957	0.3925	0.9821	0.055*	0.318 (3)
C6'	1.2763 (11)	0.4288 (3)	0.8669 (4)	0.054 (2)	0.318 (3)
H6'	1.3976	0.4113	0.8451	0.065*	0.318 (3)
C7'	1.1594 (14)	0.4655 (4)	0.8174 (3)	0.0432 (18)	0.318 (3)
H7'	1.2007	0.4731	0.7617	0.052*	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"A	0.4948	0.5157	0.8989	0.050*	0.324 (3)
H2"B	0.4406	0.4917	0.8078	0.050*	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"	0.8816	0.3659	0.8962	0.078*	0.324 (3)
C5"	1.1768 (13)	0.3865 (3)	0.8573 (6)	0.075 (4)	0.324 (3)
H5"	1.2419	0.3523	0.8698	0.089*	0.324 (3)
C6"	1.2956 (10)	0.4284 (3)	0.8234 (6)	0.065 (4)	0.324 (3)
H6"	1.4419	0.4229	0.8126	0.078*	0.324 (3)
C7"	1.2003 (12)	0.4783 (3)	0.8051 (5)	0.051 (3)	0.324 (3)
H7"	1.2815	0.5070	0.7819	0.061*	0.324 (3)
C8"	0.9863 (12)	0.4864 (2)	0.8208 (5)	0.044 (3)	0.324 (3)
C9	0.5873 (4)	0.59504 (10)	0.78359 (17)	0.0275 (6)
C10	0.6366 (4)	0.61620 (9)	0.70379 (16)	0.0213 (5)
C11	0.5021 (4)	0.66014 (9)	0.69050 (15)	0.0193 (5)
C12	0.7410 (4)	0.52265 (10)	0.61533 (16)	0.0222 (5)
C13	0.9002 (4)	0.48606 (10)	0.59728 (18)	0.0306 (6)
H13	1.0449	0.4974	0.5986	0.037*
C14	0.8469 (4)	0.43271 (11)	0.57721 (18)	0.0313 (6)
H14	0.9554	0.4075	0.5637	0.038*
C15	0.6385 (4)	0.41603 (10)	0.57666 (17)	0.0279 (6)
H15	0.6029	0.3793	0.5633	0.034*
C16	0.4805 (4)	0.45288 (10)	0.5956 (2)	0.0336 (7)
H16	0.3364	0.4412	0.5960	0.040*
C17	0.5304 (4)	0.50657 (10)	0.61392 (18)	0.0299 (6)
H17	0.4213	0.5321	0.6254	0.036*
C18	0.4762 (4)	0.69961 (9)	0.62105 (16)	0.0230 (5)
C19	0.2844 (4)	0.70325 (11)	0.57537 (16)	0.0279 (6)
H19	0.1721	0.6785	0.5860	0.033*
C20	0.2575 (5)	0.74308 (13)	0.51430 (19)	0.0420 (8)
H20	0.1263	0.7456	0.4831	0.050*
C21	0.4199 (7)	0.77902 (13)	0.4985 (2)	0.0522 (9)
H21	0.3998	0.8068	0.4575	0.063*
C22	0.6139 (6)	0.77443 (13)	0.5431 (2)	0.0519 (9)
H22	0.7273	0.7986	0.5312	0.062*
C23	0.6420 (5)	0.73508 (11)	0.60416 (18)	0.0352 (7)
H23	0.7741	0.7322	0.6347	0.042*
C24	0.2196 (4)	0.70160 (11)	0.77998 (16)	0.0273 (6)
C25	0.2472 (4)	0.75683 (11)	0.76539 (19)	0.0338 (6)
H25	0.3723	0.7698	0.7401	0.041*
C26	0.0889 (5)	0.79293 (13)	0.7884 (2)	0.0409 (7)
H26	0.1070	0.8309	0.7790	0.049*
C27	−0.0956 (4)	0.77443 (13)	0.8251 (2)	0.0406 (8)
C28	−0.1194 (4)	0.71885 (13)	0.83758 (19)	0.0383 (7)
H28	−0.2454	0.7057	0.8620	0.046*
C29	0.0362 (4)	0.68207 (12)	0.81537 (17)	0.0310 (6)
H29	0.0174	0.6441	0.8242	0.037*
C30	−0.2606 (5)	0.81477 (15)	0.8538 (2)	0.0539 (10)
H30A	−0.3979	0.7962	0.8585	0.081*
H30B	−0.2750	0.8445	0.8129	0.081*
H30C	−0.2157	0.8297	0.9087	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0197 (3)	0.0221 (3)	0.0349 (4)	−0.0019 (2)	0.0043 (3)	−0.0087 (3)
O1	0.0207 (9)	0.0356 (11)	0.0736 (16)	−0.0014 (8)	−0.0025 (10)	−0.0245 (11)
O2	0.0408 (11)	0.0249 (9)	0.0305 (10)	−0.0031 (8)	0.0153 (9)	−0.0025 (8)
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'	0.061 (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)
N3	0.0298 (12)	0.0392 (13)	0.0211 (11)	−0.0052 (10)	0.0004 (9)	0.0040 (10)
N4	0.0209 (10)	0.0268 (10)	0.0193 (10)	−0.0008 (8)	0.0009 (8)	−0.0030 (9)
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'	0.044 (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)
C9	0.0296 (13)	0.0253 (13)	0.0274 (14)	−0.0026 (11)	−0.0031 (11)	0.0049 (11)
C10	0.0210 (12)	0.0188 (11)	0.0240 (13)	−0.0009 (9)	−0.0013 (10)	−0.0032 (10)
C11	0.0178 (11)	0.0213 (11)	0.0186 (12)	−0.0043 (9)	0.0001 (9)	−0.0045 (10)
C12	0.0223 (12)	0.0224 (12)	0.0220 (13)	0.0006 (10)	−0.0002 (10)	−0.0041 (10)
C13	0.0193 (12)	0.0294 (13)	0.0431 (17)	0.0014 (10)	0.0017 (12)	−0.0059 (12)
C14	0.0283 (14)	0.0254 (13)	0.0406 (16)	0.0070 (11)	0.0065 (12)	−0.0037 (12)
C15	0.0324 (14)	0.0199 (12)	0.0317 (15)	−0.0008 (10)	0.0049 (12)	−0.0048 (11)
C16	0.0223 (13)	0.0262 (13)	0.0528 (19)	−0.0042 (11)	0.0066 (13)	−0.0061 (13)
C17	0.0197 (12)	0.0225 (12)	0.0477 (17)	0.0029 (10)	0.0034 (12)	−0.0058 (12)
C18	0.0301 (13)	0.0190 (11)	0.0200 (13)	0.0008 (10)	0.0009 (10)	−0.0017 (10)
C19	0.0293 (13)	0.0302 (13)	0.0241 (14)	0.0045 (11)	−0.0007 (11)	−0.0040 (11)
C20	0.0542 (19)	0.0457 (18)	0.0258 (15)	0.0225 (16)	−0.0046 (14)	0.0014 (14)
C21	0.094 (3)	0.0345 (17)	0.0286 (17)	0.0108 (18)	0.0036 (18)	0.0107 (14)
C22	0.083 (3)	0.0366 (17)	0.0364 (18)	−0.0200 (17)	0.0049 (18)	0.0102 (15)
C23	0.0440 (17)	0.0307 (14)	0.0307 (15)	−0.0110 (13)	−0.0007 (13)	0.0031 (12)
C24	0.0213 (12)	0.0349 (14)	0.0257 (14)	0.0010 (11)	−0.0010 (10)	−0.0155 (12)
C25	0.0258 (13)	0.0356 (15)	0.0403 (16)	−0.0025 (12)	0.0038 (12)	−0.0164 (13)
C26	0.0339 (15)	0.0380 (16)	0.0503 (19)	0.0039 (13)	−0.0052 (14)	−0.0230 (15)
C27	0.0241 (14)	0.0551 (19)	0.0420 (18)	0.0051 (13)	−0.0048 (12)	−0.0297 (15)
C28	0.0223 (13)	0.060 (2)	0.0330 (16)	−0.0050 (13)	0.0014 (12)	−0.0234 (15)
C29	0.0223 (13)	0.0443 (16)	0.0261 (14)	−0.0013 (12)	−0.0025 (11)	−0.0129 (13)
C30	0.0335 (16)	0.064 (2)	0.064 (2)	0.0130 (15)	−0.0042 (16)	−0.0388 (19)

Geometric parameters (Å, º) top

S1—O1	1.432 (2)	C1"—C9	1.512 (8)
S1—O2	1.436 (2)	C2"—H2"A	0.9900
S1—C10	1.754 (2)	C2"—H2"B	0.9900
S1—C12	1.769 (2)	C3"—C4"	1.3900
N1—C1	1.322 (9)	C3"—C8"	1.3900
N1—C8	1.375 (9)	C4"—C5"	1.3900
N2—C2	1.370 (9)	C4"—H4"	0.9500
N2—C3	1.408 (7)	C5"—C6"	1.3900
N2—N2ⁱ	1.856 (16)	C5"—H5"	0.9500
N2—H2	0.8800	C6"—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—C10	1.416 (4)
N2'—H2'	0.8800	C10—C11	1.381 (3)
N1"—C1"	1.335 (8)	C11—C18	1.474 (3)
N1"—C8"	1.361 (8)	C12—C13	1.381 (3)
N2"—C2"	1.392 (8)	C12—C17	1.380 (3)
N2"—C3"	1.400 (8)	C13—C14	1.385 (4)
N2"—H2"	0.8800	C13—H13	0.9500
N3—C9	1.328 (3)	C14—C15	1.371 (4)
N3—N4	1.355 (3)	C14—H14	0.9500
N4—C11	1.359 (3)	C15—C16	1.383 (4)
N4—C24	1.436 (3)	C15—H15	0.9500
C1—C2	1.469 (9)	C16—C17	1.382 (4)
C1—C9	1.480 (8)	C16—H16	0.9500
C2—H2A	0.9900	C17—H17	0.9500
C2—H2B	0.9900	C18—C19	1.389 (4)
C3—C4	1.3900	C18—C23	1.390 (4)
C3—C8	1.3900	C19—C20	1.384 (4)
C4—C5	1.3900	C19—H19	0.9500
C4—H4A	0.9500	C20—C21	1.378 (5)
C5—C6	1.3900	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.394 (5)
C6—C7	1.3900	C21—H21	0.9500
C6—H6	0.9500	C22—C23	1.377 (4)
C7—C8	1.3900	C22—H22	0.9500
C7—H7	0.9500	C23—H23	0.9500
C1'—C2'	1.483 (10)	C24—C29	1.385 (4)
C1'—C9	1.494 (9)	C24—C25	1.386 (4)
C2'—H2'A	0.9900	C25—C26	1.390 (4)
C2'—H2'B	0.9900	C25—H25	0.9500
C3'—C4'	1.3900	C26—C27	1.391 (4)
C3'—C8'	1.3900	C26—H26	0.9500
C4'—C5'	1.3900	C27—C28	1.386 (5)
C4'—H4'	0.9500	C27—C30	1.515 (4)
C5'—C6'	1.3900	C28—C29	1.384 (4)
C5'—H5'	0.9500	C28—H28	0.9500
C6'—C7'	1.3900	C29—H29	0.9500
C6'—H6'	0.9500	C30—H30A	0.9800
C7'—C8'	1.3900	C30—H30B	0.9800
C7'—H7'	0.9500	C30—H30C	0.9800
C1"—C2"	1.470 (9)

O1—S1—O2	116.63 (13)	C8"—C3"—N2"	122.5 (6)
O1—S1—C10	111.78 (12)	C5"—C4"—C3"	120.0
O2—S1—C10	106.57 (11)	C5"—C4"—H4"	120.0
O1—S1—C12	108.98 (12)	C3"—C4"—H4"	120.0
O2—S1—C12	107.84 (11)	C4"—C5"—C6"	120.0
C10—S1—C12	104.29 (12)	C4"—C5"—H5"	120.0
C1—N1—C8	112.2 (10)	C6"—C5"—H5"	120.0
C2—N2—C3	108.9 (9)	C7"—C6"—C5"	120.0
C2—N2—N2ⁱ	98.0 (8)	C7"—C6"—H6"	120.0
C3—N2—N2ⁱ	135.4 (9)	C5"—C6"—H6"	120.0
C2—N2—H2	125.5	C8"—C7"—C6"	120.0
C3—N2—H2	125.5	C8"—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'	118.1	N1"—C8"—C3"	122.3 (6)
C3'—N2'—H2'	118.1	C7"—C8"—C3"	120.0
C1"—N1"—C8"	117.2 (7)	N3—C9—C10	110.6 (2)
C2"—N2"—C3"	115.8 (7)	N3—C9—C1	113.7 (6)
C2"—N2"—H2"	122.1	C10—C9—C1	134.2 (6)
C3"—N2"—H2"	122.1	N3—C9—C1'	114.3 (7)
C9—N3—N4	105.3 (2)	C10—C9—C1'	135.1 (7)
N3—N4—C11	112.7 (2)	N3—C9—C1"	130.9 (4)
N3—N4—C24	118.0 (2)	C10—C9—C1"	118.0 (4)
C11—N4—C24	129.3 (2)	C11—C10—C9	105.8 (2)
N1—C1—C2	117.8 (10)	C11—C10—S1	124.51 (19)
N1—C1—C9	113.7 (8)	C9—C10—S1	129.57 (19)
C2—C1—C9	114.3 (8)	N4—C11—C10	105.6 (2)
N2—C2—C1	124.2 (11)	N4—C11—C18	121.6 (2)
N2—C2—H2A	106.3	C10—C11—C18	132.7 (2)
C1—C2—H2A	106.3	C13—C12—C17	120.8 (2)
N2—C2—H2B	106.3	C13—C12—S1	117.43 (19)
C1—C2—H2B	106.3	C17—C12—S1	121.52 (19)
H2A—C2—H2B	106.4	C12—C13—C14	119.3 (2)
C4—C3—C8	120.0	C12—C13—H13	120.3
C4—C3—N2	117.2 (5)	C14—C13—H13	120.3
C8—C3—N2	122.8 (5)	C15—C14—C13	120.5 (2)
C5—C4—C3	120.0	C15—C14—H14	119.8
C5—C4—H4A	120.0	C13—C14—H14	119.8
C3—C4—H4A	120.0	C14—C15—C16	119.7 (2)
C4—C5—C6	120.0	C14—C15—H15	120.1
C4—C5—H5	120.0	C16—C15—H15	120.1
C6—C5—H5	120.0	C15—C16—C17	120.6 (2)
C7—C6—C5	120.0	C15—C16—H16	119.7
C7—C6—H6	120.0	C17—C16—H16	119.7
C5—C6—H6	120.0	C12—C17—C16	119.1 (2)
C6—C7—C8	120.0	C12—C17—H17	120.5
C6—C7—H7	120.0	C16—C17—H17	120.5
C8—C7—H7	120.0	C19—C18—C23	120.1 (2)
N1—C8—C7	114.6 (7)	C19—C18—C11	120.5 (2)
N1—C8—C3	125.3 (7)	C23—C18—C11	119.4 (2)
C7—C8—C3	120.0	C20—C19—C18	119.8 (3)
N1'—C1'—C2'	113.9 (12)	C20—C19—H19	120.1
N1'—C1'—C9	110.2 (9)	C18—C19—H19	120.1
C2'—C1'—C9	119.7 (10)	C21—C20—C19	120.4 (3)
N2'—C2'—C1'	110.7 (11)	C21—C20—H20	119.8
N2'—C2'—H2'A	109.5	C19—C20—H20	119.8
C1'—C2'—H2'A	109.5	C20—C21—C22	119.8 (3)
N2'—C2'—H2'B	109.5	C20—C21—H21	120.1
C1'—C2'—H2'B	109.5	C22—C21—H21	120.1
H2'A—C2'—H2'B	108.1	C23—C22—C21	120.3 (3)
C4'—C3'—C8'	120.0	C23—C22—H22	119.8
C4'—C3'—N2'	118.3 (6)	C21—C22—H22	119.8
C8'—C3'—N2'	121.7 (6)	C22—C23—C18	119.7 (3)
C3'—C4'—C5'	120.0	C22—C23—H23	120.1
C3'—C4'—H4'	120.0	C18—C23—H23	120.1
C5'—C4'—H4'	120.0	C29—C24—C25	121.1 (2)
C4'—C5'—C6'	120.0	C29—C24—N4	118.4 (2)
C4'—C5'—H5'	120.0	C25—C24—N4	120.4 (2)
C6'—C5'—H5'	120.0	C24—C25—C26	118.9 (3)
C7'—C6'—C5'	120.0	C24—C25—H25	120.6
C7'—C6'—H6'	120.0	C26—C25—H25	120.6
C5'—C6'—H6'	120.0	C25—C26—C27	121.1 (3)
C6'—C7'—C8'	120.0	C25—C26—H26	119.4
C6'—C7'—H7'	120.0	C27—C26—H26	119.4
C8'—C7'—H7'	120.0	C28—C27—C26	118.4 (3)
N1'—C8'—C7'	128.0 (9)	C28—C27—C30	121.4 (3)
N1'—C8'—C3'	112.0 (9)	C26—C27—C30	120.1 (3)
C7'—C8'—C3'	120.0	C29—C28—C27	121.6 (3)
N1"—C1"—C2"	122.8 (7)	C29—C28—H28	119.2
N1"—C1"—C9	118.6 (7)	C27—C28—H28	119.2
C2"—C1"—C9	118.5 (7)	C24—C29—C28	118.9 (3)
N2"—C2"—C1"	119.1 (8)	C24—C29—H29	120.6
N2"—C2"—H2"A	107.5	C28—C29—H29	120.6
C1"—C2"—H2"A	107.5	C27—C30—H30A	109.5
N2"—C2"—H2"B	107.5	C27—C30—H30B	109.5
C1"—C2"—H2"B	107.5	H30A—C30—H30B	109.5
H2"A—C2"—H2"B	107.0	C27—C30—H30C	109.5
C4"—C3"—C8"	120.0	H30A—C30—H30C	109.5
C4"—C3"—N2"	117.5 (6)	H30B—C30—H30C	109.5

C9—N3—N4—C11	0.9 (3)	C2'—C1'—C9—N3	−26.6 (14)
C9—N3—N4—C24	−179.4 (2)	N1'—C1'—C9—C10	23.1 (17)
C8—N1—C1—C2	−29.4 (15)	C2'—C1'—C9—C10	158.1 (8)
C8—N1—C1—C9	−167.0 (9)	N1'—C1'—C9—C1	−71 (4)
C3—N2—C2—C1	−22.3 (15)	C2'—C1'—C9—C1	64 (4)
N2ⁱ—N2—C2—C1	−166.2 (11)	N1'—C1'—C9—C1"	32 (2)
N1—C1—C2—N2	37.2 (17)	C2'—C1'—C9—C1"	167 (4)
C9—C1—C2—N2	174.5 (10)	N1"—C1"—C9—N3	−147.6 (10)
C2—N2—C3—C4	−174.5 (7)	C2"—C1"—C9—N3	36.5 (13)
N2ⁱ—N2—C3—C4	−50.6 (14)	N1"—C1"—C9—C10	41.6 (14)
C2—N2—C3—C8	6.3 (11)	C2"—C1"—C9—C10	−134.3 (8)
N2ⁱ—N2—C3—C8	130.2 (11)	N1"—C1"—C9—C1	−96 (2)
C8—C3—C4—C5	0.0	C2"—C1"—C9—C1	87.9 (17)
N2—C3—C4—C5	−179.2 (7)	N1"—C1"—C9—C1'	−132 (3)
C3—C4—C5—C6	0.0	C2"—C1"—C9—C1'	53 (2)
C4—C5—C6—C7	0.0	N3—C9—C10—C11	0.3 (3)
C5—C6—C7—C8	0.0	C1—C9—C10—C11	−164.4 (7)
C1—N1—C8—C7	−167.1 (8)	C1'—C9—C10—C11	175.7 (9)
C1—N1—C8—C3	15.5 (14)	C1"—C9—C10—C11	172.9 (5)
C6—C7—C8—N1	−177.5 (8)	N3—C9—C10—S1	−175.66 (19)
C6—C7—C8—C3	0.0	C1—C9—C10—S1	19.6 (7)
C4—C3—C8—N1	177.3 (8)	C1'—C9—C10—S1	−0.3 (9)
N2—C3—C8—N1	−3.6 (10)	C1"—C9—C10—S1	−3.1 (6)
C4—C3—C8—C7	0.0	O1—S1—C10—C11	119.9 (2)
N2—C3—C8—C7	179.2 (7)	O2—S1—C10—C11	−8.6 (2)
C8'—N1'—C1'—C2'	34 (3)	C12—S1—C10—C11	−122.5 (2)
C8'—N1'—C1'—C9	172.2 (17)	O1—S1—C10—C9	−64.8 (3)
C3'—N2'—C2'—C1'	26.5 (18)	O2—S1—C10—C9	166.7 (2)
N1'—C1'—C2'—N2'	−35.5 (18)	C12—S1—C10—C9	52.8 (3)
C9—C1'—C2'—N2'	−169.0 (11)	N3—N4—C11—C10	−0.7 (3)
C2'—N2'—C3'—C4'	169.7 (10)	C24—N4—C11—C10	179.7 (2)
C2'—N2'—C3'—C8'	−10.8 (16)	N3—N4—C11—C18	−179.4 (2)
C8'—C3'—C4'—C5'	0.0	C24—N4—C11—C18	0.9 (4)
N2'—C3'—C4'—C5'	179.4 (8)	C9—C10—C11—N4	0.2 (3)
C3'—C4'—C5'—C6'	0.0	S1—C10—C11—N4	176.44 (17)
C4'—C5'—C6'—C7'	0.0	C9—C10—C11—C18	178.8 (2)
C5'—C6'—C7'—C8'	0.0	S1—C10—C11—C18	−5.0 (4)
C1'—N1'—C8'—C7'	165.9 (14)	O1—S1—C12—C13	−28.8 (3)
C1'—N1'—C8'—C3'	−17 (2)	O2—S1—C12—C13	98.7 (2)
C6'—C7'—C8'—N1'	176.9 (14)	C10—S1—C12—C13	−148.3 (2)
C6'—C7'—C8'—C3'	0.0	O1—S1—C12—C17	157.2 (2)
C4'—C3'—C8'—N1'	−177.4 (12)	O2—S1—C12—C17	−75.4 (2)
N2'—C3'—C8'—N1'	3.2 (13)	C10—S1—C12—C17	37.7 (3)
C4'—C3'—C8'—C7'	0.0	C17—C12—C13—C14	0.3 (4)
N2'—C3'—C8'—C7'	−179.4 (9)	S1—C12—C13—C14	−173.9 (2)
C8"—N1"—C1"—C2"	−4 (2)	C12—C13—C14—C15	−1.1 (4)
C8"—N1"—C1"—C9	−179.4 (10)	C13—C14—C15—C16	0.5 (4)
C3"—N2"—C2"—C1"	−2.6 (15)	C14—C15—C16—C17	0.9 (4)
N1"—C1"—C2"—N2"	2.7 (18)	C13—C12—C17—C16	1.2 (4)
C9—C1"—C2"—N2"	178.4 (9)	S1—C12—C17—C16	175.0 (2)
C2"—N2"—C3"—C4"	−176.3 (7)	C15—C16—C17—C12	−1.8 (5)
C2"—N2"—C3"—C8"	3.9 (12)	N4—C11—C18—C19	−63.1 (3)
C8"—C3"—C4"—C5"	0.0	C10—C11—C18—C19	118.5 (3)
N2"—C3"—C4"—C5"	−179.7 (9)	N4—C11—C18—C23	113.8 (3)
C3"—C4"—C5"—C6"	0.0	C10—C11—C18—C23	−64.6 (4)
C4"—C5"—C6"—C7"	0.0	C23—C18—C19—C20	−1.4 (4)
C5"—C6"—C7"—C8"	0.0	C11—C18—C19—C20	175.5 (2)
C1"—N1"—C8"—C7"	−179.9 (10)	C18—C19—C20—C21	0.1 (4)
C1"—N1"—C8"—C3"	5.0 (17)	C19—C20—C21—C22	1.4 (5)
C6"—C7"—C8"—N1"	−175.1 (10)	C20—C21—C22—C23	−1.7 (5)
C6"—C7"—C8"—C3"	0.0	C21—C22—C23—C18	0.4 (5)
C4"—C3"—C8"—N1"	174.9 (11)	C19—C18—C23—C22	1.2 (4)
N2"—C3"—C8"—N1"	−5.4 (12)	C11—C18—C23—C22	−175.7 (3)
C4"—C3"—C8"—C7"	0.0	N3—N4—C24—C29	−42.7 (3)
N2"—C3"—C8"—C7"	179.7 (9)	C11—N4—C24—C29	136.9 (3)
N4—N3—C9—C10	−0.7 (3)	N3—N4—C24—C25	136.0 (3)
N4—N3—C9—C1	167.4 (5)	C11—N4—C24—C25	−44.4 (4)
N4—N3—C9—C1'	−177.1 (7)	C29—C24—C25—C26	1.3 (4)
N4—N3—C9—C1"	−172.0 (6)	N4—C24—C25—C26	−177.4 (2)
N1—C1—C9—N3	161.6 (8)	C24—C25—C26—C27	−0.4 (4)
C2—C1—C9—N3	22.5 (11)	C25—C26—C27—C28	−0.5 (5)
N1—C1—C9—C10	−34.1 (13)	C25—C26—C27—C30	176.8 (3)
C2—C1—C9—C10	−173.2 (7)	C26—C27—C28—C29	0.7 (4)
N1—C1—C9—C1'	66 (4)	C30—C27—C28—C29	−176.6 (3)
C2—C1—C9—C1'	−73 (4)	C25—C24—C29—C28	−1.1 (4)
N1—C1—C9—C1"	21.7 (12)	N4—C24—C29—C28	177.6 (2)
C2—C1—C9—C1"	−117 (2)	C27—C28—C29—C24	0.1 (4)
N1'—C1'—C9—N3	−161.6 (12)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O1ⁱⁱ	0.95	2.57	3.430 (3)	150

Symmetry code: (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₃₀H₂₄N₄O₂S
M_r	504.59
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.2829 (2), 24.5162 (7), 15.9180 (5)
β (°)	91.925 (3)
V (Å³)	2450.51 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.20 × 0.02 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.967, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	16288, 5524, 3897
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.158, 1.02
No. of reflections	5524
No. of parameters	422
No. of restraints	139
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C19—H19···O1ⁱ	0.95	2.57	3.430 (3)	150

Symmetry code: (i) x−1, y, z.

Acknowledgements

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

References

Abdel-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
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS 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

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Volume 67| Part 3| March 2011| Page o695

doi:10.1107/S1600536811005940

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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