4-(3,5-Dimethyl-1H-pyrazol-1-yl)benzene­sulfonamide

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

doi:10.1107/S1600536811032867

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2427

doi:10.1107/S1600536811032867

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4-(3,5-Dimethyl-1H-pyrazol-1-yl)benzenesulfonamide

Abdullah M. Asiri,^a,^b Hassan M. Faidallah,^a Abdulrahman O. Al-Youbi ^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)

The two aromatic rings of the title compound, C₁₁H₁₃N₃O₂S, are inclined at an angle of 47.81 (4)°. The N atom of the amino unit is pyramidally coordinated; one H atom interacts with the sulfamyl O atom of an adjacent molecule, forming a centrosymmetric hydrogen-bonded dimer. The dimers are linked by N—H⋯N hydrogen bonds, generating a three-dimensional network.

Related literature

For the synthesis and medicinal properties of the title compound, see: Grueneberg et al. (2002 ); Wright et al. (1964 ).

Experimental

Crystal data

C₁₁H₁₃N₃O₂S
M_r = 251.30
Monoclinic, P 2₁ /n
a = 7.9649 (1) Å
b = 11.7827 (2) Å
c = 12.2720 (2) Å
β = 91.720 (1)°
V = 1151.18 (3) Å³
Z = 4
Cu Kα radiation
μ = 2.47 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.525, T_max = 0.952
8510 measured reflections
2312 independent reflections
2215 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.083
S = 1.07
2312 reflections
164 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O1ⁱ	0.87 (1)	2.13 (1)	2.966 (2)	160 (2)
N3—H1⋯N2ⁱⁱ	0.87 (1)	2.94 (2)	3.501 (2)	124 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536811032867/bt5610sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032867/bt5610Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032867/bt5610Isup3.cml

checkCIF report

Comment top

The title compound (Scheme I) was first synthesized in order to examine its anti-diabetic activity (Wright et al., 1964). It has also been listed in a virtual screening of compound libraries in order to search for possible medicinal properties (Grueneberg et al., 2002). The two aromatic rings are inclined at 47.81 (4) °. The N atom of the amino unit is pyramidally coordinated (Fig. 1). One H atom interacts with the sulfamyl O atom of an adjacent molecule to form a centrosymmetric hydrogen-bonded dimer; the dimers are linked by an N–H···N hydrogen bond to generate a layer motif.

Related literature top

For the synthesis and medicinal properties, see: Grueneberg et al. (2002); Wright et al. (1964).

Experimental top

2,4-Pentanedione (10 mmol) and 4-hydrazinobenzenesulfonamide hydrochloride (10 mmol) were heated in ethanol (50 ml) for 4 h; water was then added to precipitate the product. This was collected and recrystallized from ethanol to yield orange crystals; m.p. 516–517 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 C₁₁H₁₃N₃O₂S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

4-(3,5-Dimethyl-1H-pyrazol-1-yl)benzenesulfonamide top

Crystal data top

C₁₁H₁₃N₃O₂S	F(000) = 528
M_r = 251.30	D_x = 1.450 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 6177 reflections
a = 7.9649 (1) Å	θ = 3.6–74.0°
b = 11.7827 (2) Å	µ = 2.47 mm⁻¹
c = 12.2720 (2) Å	T = 100 K
β = 91.720 (1)°	Plate, orange
V = 1151.18 (3) Å³	0.30 × 0.20 × 0.02 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2312 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2215 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.018
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.2°, θ_min = 5.2°
ω scans	h = −7→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→14
T_min = 0.525, T_max = 0.952	l = −15→15
8510 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0441P)² + 0.7227P] where P = (F_o² + 2F_c²)/3
2312 reflections	(Δ/σ)_max = 0.001
164 parameters	Δρ_max = 0.35 e Å⁻³
2 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₁H₁₃N₃O₂S	V = 1151.18 (3) Å³
M_r = 251.30	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 7.9649 (1) Å	µ = 2.47 mm⁻¹
b = 11.7827 (2) Å	T = 100 K
c = 12.2720 (2) Å	0.30 × 0.20 × 0.02 mm
β = 91.720 (1)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2312 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2215 reflections with I > 2σ(I)
T_min = 0.525, T_max = 0.952	R_int = 0.018
8510 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	2 restraints
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.35 e Å⁻³
2312 reflections	Δρ_min = −0.41 e Å⁻³
164 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.60099 (4)	0.32597 (3)	0.50334 (2)	0.01314 (12)
O1	0.44016 (12)	0.37270 (8)	0.52982 (8)	0.0170 (2)
O2	0.65114 (14)	0.21872 (9)	0.54890 (8)	0.0208 (2)
N1	0.61599 (14)	0.27786 (10)	0.02059 (9)	0.0136 (2)
N2	0.55511 (14)	0.18062 (10)	−0.02758 (9)	0.0143 (2)
N3	0.74013 (15)	0.41830 (10)	0.54060 (9)	0.0152 (2)
C1	0.7815 (2)	0.45338 (13)	−0.02125 (12)	0.0232 (3)
H1A	0.8510	0.4777	−0.0815	0.035*
H1B	0.8535	0.4386	0.0434	0.035*
H1C	0.7007	0.5132	−0.0049	0.035*
C2	0.68933 (17)	0.34759 (12)	−0.05284 (11)	0.0161 (3)
C3	0.67052 (18)	0.29522 (12)	−0.15234 (11)	0.0170 (3)
H3	0.7068	0.3228	−0.2205	0.020*
C4	0.58685 (17)	0.19256 (12)	−0.13311 (11)	0.0147 (3)
C5	0.53563 (19)	0.10247 (13)	−0.21321 (11)	0.0196 (3)
H5A	0.4668	0.0456	−0.1771	0.029*
H5B	0.6361	0.0660	−0.2413	0.029*
H5C	0.4705	0.1367	−0.2737	0.029*
C6	0.61070 (16)	0.28964 (12)	0.13566 (11)	0.0136 (3)
C7	0.55663 (18)	0.39093 (12)	0.18128 (11)	0.0183 (3)
H7	0.5220	0.4521	0.1355	0.022*
C8	0.55342 (18)	0.40237 (12)	0.29364 (11)	0.0179 (3)
H8	0.5176	0.4715	0.3253	0.021*
C9	0.60328 (17)	0.31154 (11)	0.35950 (11)	0.0137 (3)
C10	0.65597 (18)	0.21010 (12)	0.31423 (11)	0.0163 (3)
H10	0.6891	0.1485	0.3600	0.020*
C11	0.66000 (18)	0.19918 (12)	0.20165 (11)	0.0163 (3)
H11	0.6963	0.1302	0.1700	0.020*
H1	0.712 (2)	0.4870 (10)	0.5225 (15)	0.029 (5)*
H2	0.8410 (14)	0.3966 (16)	0.5246 (16)	0.029 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01682 (19)	0.01279 (19)	0.00991 (18)	0.00155 (11)	0.00214 (12)	−0.00074 (11)
O1	0.0163 (5)	0.0191 (5)	0.0160 (5)	0.0001 (4)	0.0045 (4)	−0.0025 (4)
O2	0.0332 (6)	0.0157 (5)	0.0138 (5)	0.0049 (4)	0.0028 (4)	0.0018 (4)
N1	0.0153 (6)	0.0143 (6)	0.0110 (5)	−0.0028 (4)	−0.0002 (4)	−0.0017 (4)
N2	0.0142 (5)	0.0159 (6)	0.0128 (6)	−0.0034 (4)	0.0002 (4)	−0.0028 (4)
N3	0.0144 (6)	0.0161 (6)	0.0150 (6)	0.0024 (4)	−0.0003 (4)	−0.0027 (4)
C1	0.0300 (8)	0.0207 (7)	0.0187 (7)	−0.0104 (6)	−0.0052 (6)	0.0036 (6)
C2	0.0169 (6)	0.0165 (7)	0.0149 (6)	−0.0024 (5)	−0.0014 (5)	0.0036 (5)
C3	0.0194 (7)	0.0199 (7)	0.0117 (6)	−0.0022 (5)	−0.0005 (5)	0.0028 (5)
C4	0.0141 (6)	0.0183 (7)	0.0114 (6)	0.0002 (5)	−0.0011 (5)	−0.0011 (5)
C5	0.0248 (7)	0.0209 (7)	0.0130 (6)	−0.0018 (6)	−0.0006 (5)	−0.0039 (5)
C6	0.0123 (6)	0.0173 (7)	0.0113 (6)	−0.0025 (5)	0.0001 (5)	−0.0018 (5)
C7	0.0222 (7)	0.0173 (7)	0.0151 (7)	0.0050 (5)	−0.0033 (5)	0.0003 (5)
C8	0.0219 (7)	0.0160 (7)	0.0157 (7)	0.0048 (5)	−0.0012 (5)	−0.0033 (5)
C9	0.0136 (6)	0.0159 (6)	0.0117 (6)	−0.0005 (5)	0.0012 (5)	−0.0015 (5)
C10	0.0221 (7)	0.0130 (6)	0.0140 (6)	0.0014 (5)	0.0032 (5)	0.0016 (5)
C11	0.0213 (7)	0.0128 (6)	0.0148 (7)	0.0000 (5)	0.0039 (5)	−0.0020 (5)

Geometric parameters (Å, º) top

S1—O2	1.4338 (10)	C3—H3	0.9500
S1—O1	1.4404 (10)	C4—C5	1.4952 (19)
S1—N3	1.6094 (12)	C5—H5A	0.9800
S1—C9	1.7741 (14)	C5—H5B	0.9800
N1—C2	1.3638 (18)	C5—H5C	0.9800
N1—N2	1.3713 (15)	C6—C11	1.3881 (19)
N1—C6	1.4208 (17)	C6—C7	1.392 (2)
N2—C4	1.3344 (18)	C7—C8	1.3864 (19)
N3—H1	0.869 (9)	C7—H7	0.9500
N3—H2	0.871 (9)	C8—C9	1.3918 (19)
C1—C2	1.4920 (19)	C8—H8	0.9500
C1—H1A	0.9800	C9—C10	1.3882 (19)
C1—H1B	0.9800	C10—C11	1.3889 (19)
C1—H1C	0.9800	C10—H10	0.9500
C2—C3	1.372 (2)	C11—H11	0.9500
C3—C4	1.404 (2)

O2—S1—O1	119.22 (6)	N2—C4—C5	120.48 (12)
O2—S1—N3	107.68 (6)	C3—C4—C5	128.50 (13)
O1—S1—N3	106.68 (6)	C4—C5—H5A	109.5
O2—S1—C9	107.00 (6)	C4—C5—H5B	109.5
O1—S1—C9	107.27 (6)	H5A—C5—H5B	109.5
N3—S1—C9	108.66 (6)	C4—C5—H5C	109.5
C2—N1—N2	111.80 (11)	H5A—C5—H5C	109.5
C2—N1—C6	128.61 (11)	H5B—C5—H5C	109.5
N2—N1—C6	119.31 (11)	C11—C6—C7	120.61 (12)
C4—N2—N1	104.80 (11)	C11—C6—N1	119.24 (12)
S1—N3—H1	112.6 (13)	C7—C6—N1	120.15 (12)
S1—N3—H2	111.7 (13)	C8—C7—C6	119.90 (13)
H1—N3—H2	116.9 (18)	C8—C7—H7	120.0
C2—C1—H1A	109.5	C6—C7—H7	120.0
C2—C1—H1B	109.5	C7—C8—C9	119.29 (13)
H1A—C1—H1B	109.5	C7—C8—H8	120.4
C2—C1—H1C	109.5	C9—C8—H8	120.4
H1A—C1—H1C	109.5	C10—C9—C8	120.94 (13)
H1B—C1—H1C	109.5	C10—C9—S1	119.54 (10)
N1—C2—C3	106.24 (12)	C8—C9—S1	119.52 (10)
N1—C2—C1	123.29 (13)	C9—C10—C11	119.61 (13)
C3—C2—C1	130.28 (13)	C9—C10—H10	120.2
C2—C3—C4	106.11 (12)	C11—C10—H10	120.2
C2—C3—H3	126.9	C6—C11—C10	119.64 (13)
C4—C3—H3	126.9	C6—C11—H11	120.2
N2—C4—C3	111.01 (12)	C10—C11—H11	120.2

C2—N1—N2—C4	−1.97 (15)	C11—C6—C7—C8	0.7 (2)
C6—N1—N2—C4	−176.38 (11)	N1—C6—C7—C8	−179.31 (12)
N2—N1—C2—C3	1.89 (15)	C6—C7—C8—C9	−0.5 (2)
C6—N1—C2—C3	175.64 (13)	C7—C8—C9—C10	0.0 (2)
N2—N1—C2—C1	−173.51 (13)	C7—C8—C9—S1	179.52 (11)
C6—N1—C2—C1	0.2 (2)	O2—S1—C9—C10	−2.85 (13)
N1—C2—C3—C4	−1.01 (15)	O1—S1—C9—C10	−131.88 (12)
C1—C2—C3—C4	173.95 (15)	N3—S1—C9—C10	113.15 (12)
N1—N2—C4—C3	1.28 (15)	O2—S1—C9—C8	177.63 (11)
N1—N2—C4—C5	−179.21 (12)	O1—S1—C9—C8	48.60 (13)
C2—C3—C4—N2	−0.18 (16)	N3—S1—C9—C8	−66.37 (13)
C2—C3—C4—C5	−179.65 (14)	C8—C9—C10—C11	0.4 (2)
C2—N1—C6—C11	−128.45 (15)	S1—C9—C10—C11	−179.13 (11)
N2—N1—C6—C11	44.90 (17)	C7—C6—C11—C10	−0.3 (2)
C2—N1—C6—C7	51.5 (2)	N1—C6—C11—C10	179.71 (12)
N2—N1—C6—C7	−135.12 (13)	C9—C10—C11—C6	−0.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O1ⁱ	0.87 (1)	2.13 (1)	2.966 (2)	160 (2)
N3—H1···N2ⁱⁱ	0.87 (1)	2.94 (2)	3.501 (2)	124 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃N₃O₂S
M_r	251.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.9649 (1), 11.7827 (2), 12.2720 (2)
β (°)	91.720 (1)
V (Å³)	1151.18 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.47
Crystal size (mm)	0.30 × 0.20 × 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	0.525, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	8510, 2312, 2215
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.083, 1.07
No. of reflections	2312
No. of parameters	164
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)	0.35, −0.41

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···O1ⁱ	0.87 (1)	2.13 (1)	2.966 (2)	160 (2)
N3—H1···N2ⁱⁱ	0.87 (1)	2.94 (2)	3.501 (2)	124 (2)

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

Acknowledgements

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

References

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