4-(5-Oxo-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzene­sulfonamide

Al-Youbi, A.O.; Asiri, A.M.; Faidallah, H.M.; Alamry, K.A.; Ng, S.W.

doi:10.1107/S1600536811032879

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2428

doi:10.1107/S1600536811032879

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4-(5-Oxo-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide

Abdulrahman O. Al-Youbi,^a Abdullah M. Asiri,^a,^b Hassan M. Faidallah,^a Khalid A. Alamry ^a and Seik Weng Ng ^c,^a ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, ^bCenter of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 11 August 2011; accepted 13 August 2011; online 27 August 2011)

With respect to the aliphatic planar five-membered ring (r.m.s. deviation = 0.011 Å) of the title compound, C₁₅H₁₃N₃O₂S, the phenyl ring is aligned at 6.9 (1)° and the phenylene ring at 2.4 (1)°, so that the three rings are nearly coplanar. The amino group has the N atom in a pyramidal geometry; the group is a hydrogen-bond donor to the sulfonyl O atom of one molecule and to the ketonic O atom of another molecule, resulting in the formation of a layer parallel to the bc plane.

Related literature

For the synthesis, see: Casoni (1956 ); Itano (1955 ).

Experimental

Crystal data

C₁₅H₁₃N₃O₃S
M_r = 315.34
Monoclinic, P 2₁ /c
a = 13.6794 (4) Å
b = 13.4304 (4) Å
c = 7.3678 (2) Å
β = 91.055 (3)°
V = 1353.38 (7) Å³
Z = 4
Cu Kα radiation
μ = 2.29 mm⁻¹
T = 100 K
0.30 × 0.05 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.546, T_max = 0.894
10404 measured reflections
2731 independent reflections
2444 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.121
S = 1.06
2731 reflections
207 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O3ⁱ	0.88 (1)	2.12 (1)	2.975 (2)	164 (2)
N3—H2⋯O2ⁱⁱ	0.87 (1)	2.12 (1)	2.978 (2)	168 (2)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536811032879/bt5611sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032879/bt5611Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032879/bt5611Isup3.cml

checkCIF report

Comment top

We are examining the medicinal properties of phenylpyrazolones of which the 4-benzenesulfamide derivative (Scheme I) is expected to show enhanced activity. The synthesis of the compound was reported a long time ago (Casoni, 1956; Itano, 1955). With respect to the aliphatic planar five-membered ring, the phenyl ring is aligned at 6.9 (1)° and the phenylene ring at 2.4 (1)°. The amino group is hydrogen bond donor to the sulfonyl O atom of one molecule and to the ketonic O atom of another molecule to result in the formation of a layer parallel to the bc plane.

Related literature top

For the synthesis, see: Casoni (1956); Itano (1955).

Experimental top

Ethyl benzoylacetate (10 mmol) and 4-hydrazinobenzenesulfonamide hydrochloride (10 mmol) were heated in ethanol (50 ml) for 4 h; water was added to precipitate the product, which was collected and recrystallized from ethanol as brownish-orange crystals; m.p. 510–511 K.

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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₅H₁₃N₃O₂S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

4-(5-Oxo-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide top

Crystal data top

C₁₅H₁₃N₃O₃S	F(000) = 656
M_r = 315.34	D_x = 1.548 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4563 reflections
a = 13.6794 (4) Å	θ = 3.2–74.4°
b = 13.4304 (4) Å	µ = 2.29 mm⁻¹
c = 7.3678 (2) Å	T = 100 K
β = 91.055 (3)°	Prism, brown orange
V = 1353.38 (7) Å³	0.30 × 0.05 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2731 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2444 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.041
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.5°, θ_min = 3.2°
ω scan	h = −17→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −16→16
T_min = 0.546, T_max = 0.894	l = −5→9
10404 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0759P)² + 0.5321P] where P = (F_o² + 2F_c²)/3
2731 reflections	(Δ/σ)_max = 0.001
207 parameters	Δρ_max = 0.73 e Å⁻³
2 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₅H₁₃N₃O₃S	V = 1353.38 (7) Å³
M_r = 315.34	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 13.6794 (4) Å	µ = 2.29 mm⁻¹
b = 13.4304 (4) Å	T = 100 K
c = 7.3678 (2) Å	0.30 × 0.05 × 0.05 mm
β = 91.055 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2731 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2444 reflections with I > 2σ(I)
T_min = 0.546, T_max = 0.894	R_int = 0.041
10404 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	2 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.73 e Å⁻³
2731 reflections	Δρ_min = −0.51 e Å⁻³
207 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.

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

	x	y	z	U_iso*/U_eq
S1	0.91654 (3)	0.64477 (3)	0.49527 (6)	0.01653 (16)
O1	0.52785 (10)	0.32661 (11)	0.6467 (2)	0.0319 (4)
O2	0.90632 (9)	0.74972 (10)	0.46298 (18)	0.0220 (3)
O3	0.95114 (9)	0.58212 (10)	0.35168 (17)	0.0209 (3)
N2	0.46514 (11)	0.56244 (12)	0.8066 (2)	0.0203 (3)
N3	0.99249 (12)	0.63163 (12)	0.6642 (2)	0.0197 (3)
H1	1.0122 (17)	0.5704 (9)	0.682 (3)	0.028 (6)*
H2	0.9740 (16)	0.6620 (16)	0.763 (2)	0.023 (6)*
N1	0.52929 (11)	0.49471 (11)	0.7246 (2)	0.0197 (3)
C1	0.49011 (14)	0.39912 (14)	0.7147 (3)	0.0227 (4)
C2	0.39264 (14)	0.40640 (14)	0.8033 (3)	0.0224 (4)
H2A	0.3390	0.3864	0.7189	0.027*
H2B	0.3903	0.3645	0.9138	0.027*
C3	0.38673 (13)	0.51403 (14)	0.8491 (2)	0.0198 (4)
C4	0.30272 (13)	0.56293 (14)	0.9324 (2)	0.0205 (4)
C5	0.30792 (15)	0.66235 (15)	0.9877 (3)	0.0261 (4)
H5	0.3663	0.6993	0.9713	0.031*
C6	0.22764 (16)	0.70694 (16)	1.0664 (3)	0.0312 (5)
H6	0.2311	0.7745	1.1040	0.037*
C7	0.14192 (15)	0.65297 (16)	1.0905 (3)	0.0294 (5)
H7	0.0870	0.6837	1.1441	0.035*
C8	0.13695 (14)	0.55477 (17)	1.0363 (3)	0.0281 (5)
H8	0.0784	0.5181	1.0528	0.034*
C9	0.21695 (13)	0.50911 (15)	0.9577 (3)	0.0235 (4)
H9	0.2132	0.4413	0.9213	0.028*
C10	0.62051 (12)	0.52987 (13)	0.6675 (2)	0.0178 (4)
C11	0.68801 (13)	0.46447 (14)	0.5912 (2)	0.0197 (4)
H11	0.6720	0.3961	0.5759	0.024*
C12	0.77831 (13)	0.49990 (13)	0.5381 (2)	0.0184 (4)
H12	0.8246	0.4557	0.4875	0.022*
C13	0.80101 (13)	0.60030 (13)	0.5590 (2)	0.0175 (4)
C14	0.73339 (14)	0.66554 (14)	0.6338 (3)	0.0201 (4)
H14	0.7495	0.7339	0.6481	0.024*
C15	0.64299 (14)	0.63125 (14)	0.6873 (3)	0.0200 (4)
H15	0.5967	0.6759	0.7369	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0140 (2)	0.0175 (3)	0.0182 (3)	−0.00041 (14)	0.00381 (17)	0.00075 (14)
O1	0.0230 (7)	0.0225 (7)	0.0506 (9)	−0.0015 (6)	0.0103 (7)	−0.0049 (6)
O2	0.0202 (6)	0.0184 (7)	0.0276 (7)	−0.0010 (5)	0.0052 (5)	0.0040 (5)
O3	0.0194 (6)	0.0241 (7)	0.0194 (6)	−0.0005 (5)	0.0061 (5)	−0.0021 (5)
N2	0.0148 (7)	0.0241 (8)	0.0221 (8)	0.0014 (6)	0.0047 (6)	−0.0003 (6)
N3	0.0180 (8)	0.0205 (8)	0.0208 (8)	0.0015 (6)	0.0012 (6)	−0.0009 (6)
N1	0.0161 (7)	0.0206 (8)	0.0226 (8)	−0.0004 (6)	0.0050 (6)	−0.0023 (6)
C1	0.0194 (9)	0.0227 (10)	0.0259 (9)	−0.0017 (7)	0.0013 (7)	0.0021 (7)
C2	0.0179 (9)	0.0251 (10)	0.0242 (9)	−0.0018 (7)	0.0024 (7)	0.0015 (7)
C3	0.0168 (9)	0.0248 (9)	0.0178 (8)	−0.0014 (7)	0.0008 (7)	0.0022 (7)
C4	0.0162 (9)	0.0274 (9)	0.0179 (8)	0.0009 (7)	0.0022 (7)	0.0049 (7)
C5	0.0236 (10)	0.0259 (10)	0.0290 (10)	0.0004 (8)	0.0083 (8)	0.0056 (8)
C6	0.0326 (11)	0.0261 (10)	0.0353 (11)	0.0068 (8)	0.0120 (9)	0.0078 (8)
C7	0.0220 (10)	0.0400 (12)	0.0266 (10)	0.0123 (8)	0.0080 (8)	0.0114 (8)
C8	0.0153 (9)	0.0450 (12)	0.0241 (10)	−0.0017 (8)	0.0019 (7)	0.0068 (8)
C9	0.0180 (9)	0.0329 (10)	0.0195 (9)	−0.0034 (8)	0.0007 (7)	0.0007 (7)
C10	0.0146 (8)	0.0220 (9)	0.0170 (8)	−0.0006 (7)	0.0012 (6)	0.0019 (7)
C11	0.0190 (9)	0.0203 (9)	0.0200 (8)	−0.0009 (7)	0.0019 (7)	−0.0004 (7)
C12	0.0161 (8)	0.0193 (8)	0.0199 (9)	0.0024 (7)	0.0029 (7)	0.0004 (6)
C13	0.0141 (8)	0.0208 (9)	0.0178 (8)	−0.0012 (7)	0.0015 (6)	0.0019 (6)
C14	0.0195 (9)	0.0171 (8)	0.0240 (9)	−0.0002 (7)	0.0033 (7)	0.0000 (7)
C15	0.0177 (9)	0.0211 (9)	0.0213 (9)	0.0017 (7)	0.0029 (7)	−0.0007 (7)

Geometric parameters (Å, º) top

S1—O2	1.4358 (13)	C5—H5	0.9500
S1—O3	1.4386 (13)	C6—C7	1.393 (3)
S1—N3	1.6160 (17)	C6—H6	0.9500
S1—C13	1.7611 (18)	C7—C8	1.379 (3)
O1—C1	1.215 (2)	C7—H7	0.9500
N2—C3	1.298 (2)	C8—C9	1.390 (3)
N2—N1	1.408 (2)	C8—H8	0.9500
N3—H1	0.875 (10)	C9—H9	0.9500
N3—H2	0.873 (10)	C10—C11	1.400 (2)
N1—C1	1.393 (2)	C10—C15	1.403 (3)
N1—C10	1.406 (2)	C11—C12	1.387 (3)
C1—C2	1.499 (3)	C11—H11	0.9500
C2—C3	1.487 (3)	C12—C13	1.392 (2)
C2—H2A	0.9900	C12—H12	0.9500
C2—H2B	0.9900	C13—C14	1.395 (2)
C3—C4	1.468 (2)	C14—C15	1.384 (3)
C4—C9	1.393 (3)	C14—H14	0.9500
C4—C5	1.397 (3)	C15—H15	0.9500
C5—C6	1.387 (3)

O2—S1—O3	119.00 (8)	C5—C6—C7	120.2 (2)
O2—S1—N3	107.10 (8)	C5—C6—H6	119.9
O3—S1—N3	106.67 (8)	C7—C6—H6	119.9
O2—S1—C13	106.97 (8)	C8—C7—C6	119.86 (19)
O3—S1—C13	107.85 (8)	C8—C7—H7	120.1
N3—S1—C13	108.97 (8)	C6—C7—H7	120.1
C3—N2—N1	107.72 (15)	C7—C8—C9	120.49 (19)
S1—N3—H1	114.1 (16)	C7—C8—H8	119.8
S1—N3—H2	113.3 (16)	C9—C8—H8	119.8
H1—N3—H2	114 (2)	C8—C9—C4	119.88 (19)
C1—N1—C10	129.54 (15)	C8—C9—H9	120.1
C1—N1—N2	112.08 (14)	C4—C9—H9	120.1
C10—N1—N2	118.38 (14)	C11—C10—N1	120.35 (16)
O1—C1—N1	126.49 (17)	C11—C10—C15	120.39 (16)
O1—C1—C2	128.35 (18)	N1—C10—C15	119.26 (16)
N1—C1—C2	105.17 (16)	C12—C11—C10	119.71 (17)
C3—C2—C1	102.40 (15)	C12—C11—H11	120.1
C3—C2—H2A	111.3	C10—C11—H11	120.1
C1—C2—H2A	111.3	C11—C12—C13	119.97 (16)
C3—C2—H2B	111.3	C11—C12—H12	120.0
C1—C2—H2B	111.3	C13—C12—H12	120.0
H2A—C2—H2B	109.2	C12—C13—C14	120.26 (16)
N2—C3—C4	122.26 (17)	C12—C13—S1	119.91 (13)
N2—C3—C2	112.57 (16)	C14—C13—S1	119.81 (14)
C4—C3—C2	125.17 (16)	C15—C14—C13	120.41 (17)
C9—C4—C5	119.68 (17)	C15—C14—H14	119.8
C9—C4—C3	119.44 (17)	C13—C14—H14	119.8
C5—C4—C3	120.88 (17)	C14—C15—C10	119.25 (17)
C6—C5—C4	119.85 (19)	C14—C15—H15	120.4
C6—C5—H5	120.1	C10—C15—H15	120.4
C4—C5—H5	120.1

C3—N2—N1—C1	−0.1 (2)	C5—C4—C9—C8	0.5 (3)
C3—N2—N1—C10	−179.52 (16)	C3—C4—C9—C8	−179.92 (17)
C10—N1—C1—O1	−2.7 (3)	C1—N1—C10—C11	−1.6 (3)
N2—N1—C1—O1	177.9 (2)	N2—N1—C10—C11	177.72 (15)
C10—N1—C1—C2	177.83 (17)	C1—N1—C10—C15	178.21 (18)
N2—N1—C1—C2	−1.6 (2)	N2—N1—C10—C15	−2.4 (2)
O1—C1—C2—C3	−177.1 (2)	N1—C10—C11—C12	−178.97 (16)
N1—C1—C2—C3	2.34 (19)	C15—C10—C11—C12	1.2 (3)
N1—N2—C3—C4	−178.03 (16)	C10—C11—C12—C13	−0.7 (3)
N1—N2—C3—C2	1.7 (2)	C11—C12—C13—C14	0.2 (3)
C1—C2—C3—N2	−2.6 (2)	C11—C12—C13—S1	178.85 (14)
C1—C2—C3—C4	177.17 (17)	O2—S1—C13—C12	157.60 (15)
N2—C3—C4—C9	173.44 (17)	O3—S1—C13—C12	28.50 (17)
C2—C3—C4—C9	−6.3 (3)	N3—S1—C13—C12	−86.93 (16)
N2—C3—C4—C5	−7.0 (3)	O2—S1—C13—C14	−23.78 (17)
C2—C3—C4—C5	173.27 (18)	O3—S1—C13—C14	−152.88 (15)
C9—C4—C5—C6	−0.3 (3)	N3—S1—C13—C14	91.69 (16)
C3—C4—C5—C6	−179.88 (18)	C12—C13—C14—C15	−0.3 (3)
C4—C5—C6—C7	0.0 (3)	S1—C13—C14—C15	−178.89 (14)
C5—C6—C7—C8	0.2 (3)	C13—C14—C15—C10	0.8 (3)
C6—C7—C8—C9	0.0 (3)	C11—C10—C15—C14	−1.2 (3)
C7—C8—C9—C4	−0.4 (3)	N1—C10—C15—C14	178.94 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O3ⁱ	0.88 (1)	2.12 (1)	2.975 (2)	164 (2)
N3—H2···O2ⁱⁱ	0.87 (1)	2.12 (1)	2.978 (2)	168 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₃O₃S
M_r	315.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.6794 (4), 13.4304 (4), 7.3678 (2)
β (°)	91.055 (3)
V (Å³)	1353.38 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.29
Crystal size (mm)	0.30 × 0.05 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.546, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	10404, 2731, 2444
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.121, 1.06
No. of reflections	2731
No. of parameters	207
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.51

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
N3—H1···O3ⁱ	0.88 (1)	2.12 (1)	2.975 (2)	164 (2)
N3—H2···O2ⁱⁱ	0.87 (1)	2.12 (1)	2.978 (2)	168 (2)

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

Acknowledgements

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

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