4-{2-[(E)-Cyclo­pentyl­idene]hydrazin-1-yl}benzene­sulfonamide

Al-Youbi, A.O.; Asiri, A.M.; Faidallah, H.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812012524

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1196

doi:10.1107/S1600536812012524

Open

access

4-{2-[(E)-Cyclopentylidene]hydrazin-1-yl}benzenesulfonamide

Abdulrahman O. Al-Youbi,^a,^b Abdullah M. Asiri,^a,^b ‡ Hassan M. Faidallah,^a Seik Weng Ng ^c and Edward R. T. Tiekink ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, ^bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, PO Box 80203, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 8 March 2012; accepted 22 March 2012; online 28 March 2012)

The title molecule, C₁₁H₁₅N₃O₂S, features a five-membered ring which is twisted about the middle CH₂—CH₂ bond. The benzene ring is inclined with respect to the imine residue [C—N—N—C torsion angle = 165.4 (2)°]. Supramolecular layers in the bc plane are formed by hydrogen bonds between the amine H atoms and sulfonamide O and imine N atoms, as well as by a weak hydrazine H-atom intermolecular interaction with the second sulfonamide O atom.

Related literature

For background to the biological applications of related sulfonamides, see: Al-Saadi et al. (2008 ). For related structures, see: Asiri et al. (2011 , 2012 ).

Experimental

Crystal data

C₁₁H₁₅N₃O₂S
M_r = 253.32
Monoclinic, P 2₁ /c
a = 14.1173 (14) Å
b = 5.2038 (5) Å
c = 16.4239 (19) Å
β = 94.019 (10)°
V = 1203.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100 K
0.35 × 0.05 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.914, T_max = 0.995
4782 measured reflections
2768 independent reflections
2007 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.123
S = 1.03
2768 reflections
166 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88 (1)	2.02 (1)	2.869 (3)	164 (3)
N1—H2⋯N3ⁱⁱ	0.88 (1)	2.13 (1)	2.993 (3)	166 (3)
N2—H3⋯O2ⁱⁱⁱ	0.88 (1)	2.36 (1)	3.220 (3)	166 (3)
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); 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: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812012524/jj2126sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012524/jj2126Isup2.hkl

checkCIF report

Comment top

Sulfonamides related to the title compound, 4-(N-cyclopentylidenehydrazino)benzensulfonamide (I), have been shown to display biological activity (Al-Saadi et al., 2008). In continuation of structural studies of these sulfonamides (Asiri et al., 2011; Asiri et al., 2012), the crystal and molecular structure of (I) is reported herein.

In (I), Fig. 1, the five-membered ring is twisted about the C9—C10 bond. The imine residue is not co-planar with the benzene ring with a twist apparent about the N2—C4 bond; the C4—N2—N3—C7 torsion angle is 165.4 (2)°.

The crystal packing is dominated by N—H···O and N—H···N hydrogen bonds. The amino-H atoms form hydrogen bonds with a sulfonamide-O and imine-N atoms. The hydrazine-H atom forms a weak intermolecular interaction with the second sulfonamide-O atom, Table 1. The result is the formation of supramolecular layers in the bc plane, Fig. 2. Layers stack along the a axis with no specific intermolecular interactions between them.

Related literature top

For background to the biological applications of related sulfonamides, see: Al-Saadi et al. (2008). For related structures, see: Asiri et al. (2011, 2012).

Experimental top

Cyclopentanone (0.84 g, 10 mmol) in ethanol was refluxed with p-sulfamylphenylhydrazine (2.2 g, 10 mmol) for 1 h. The reaction mixture was cooled and the precipitated product was collected by filtration, washed with ethanol, dried and recrystallized from its ethanol solution. Yield: 78%. M. pt: 475–477 K.

Structure description top

For background to the biological applications of related sulfonamides, see: Al-Saadi et al. (2008). For related structures, see: Asiri et al. (2011, 2012).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular layer in the bc plane in (I). The N—H···O and N—H···N hydrogen bonds are shown as orange and blue dashed lines, respectively.
	Fig. 3. A view in projection down the b axis of the unit-cell contents of (I) showing the stacking of layers along the a axis. The N—H···O and N—H···N interactions are shown as orange and blue dashed lines, respectively.

4-{2-[(E)-Cyclopentylidene]hydrazin-1-yl}benzenesulfonamide top

Crystal data top

C₁₁H₁₅N₃O₂S	F(000) = 536
M_r = 253.32	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1078 reflections
a = 14.1173 (14) Å	θ = 2.5–27.5°
b = 5.2038 (5) Å	µ = 0.26 mm⁻¹
c = 16.4239 (19) Å	T = 100 K
β = 94.019 (10)°	Plate, colourless
V = 1203.6 (2) Å³	0.35 × 0.05 × 0.02 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2768 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2007 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.044
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.5°
ω scan	h = −18→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −4→6
T_min = 0.914, T_max = 0.995	l = −21→21
4782 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0372P)² + 0.8414P] where P = (F_o² + 2F_c²)/3
2768 reflections	(Δ/σ)_max = 0.001
166 parameters	Δρ_max = 0.32 e Å⁻³
3 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₁H₁₅N₃O₂S	V = 1203.6 (2) Å³
M_r = 253.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.1173 (14) Å	µ = 0.26 mm⁻¹
b = 5.2038 (5) Å	T = 100 K
c = 16.4239 (19) Å	0.35 × 0.05 × 0.02 mm
β = 94.019 (10)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2768 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2007 reflections with I > 2σ(I)
T_min = 0.914, T_max = 0.995	R_int = 0.044
4782 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	3 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.32 e Å⁻³
2768 reflections	Δρ_min = −0.38 e Å⁻³
166 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.28398 (5)	0.43647 (12)	0.35890 (4)	0.01924 (18)
O1	0.26446 (13)	0.1919 (3)	0.39559 (13)	0.0304 (5)
O2	0.25331 (13)	0.4780 (4)	0.27417 (11)	0.0276 (5)
N1	0.23242 (16)	0.6501 (4)	0.41081 (14)	0.0185 (5)
H1	0.238 (2)	0.811 (2)	0.3960 (17)	0.028 (8)*
H2	0.244 (2)	0.626 (6)	0.4636 (7)	0.042 (10)*
N2	0.70084 (16)	0.5585 (5)	0.36168 (14)	0.0238 (5)
H3	0.7234 (19)	0.672 (4)	0.3286 (14)	0.025 (8)*
N3	0.76230 (15)	0.4003 (4)	0.40739 (13)	0.0210 (5)
C1	0.40782 (17)	0.4817 (5)	0.36814 (15)	0.0172 (5)
C2	0.46722 (18)	0.3075 (5)	0.41081 (15)	0.0192 (6)
H2A	0.4406	0.1709	0.4401	0.023*
C3	0.56513 (18)	0.3314 (5)	0.41102 (16)	0.0199 (6)
H3A	0.6054	0.2114	0.4400	0.024*
C4	0.60411 (18)	0.5343 (5)	0.36816 (15)	0.0182 (5)
C5	0.54389 (18)	0.7151 (5)	0.32815 (16)	0.0193 (6)
H5	0.5703	0.8571	0.3012	0.023*
C6	0.44676 (18)	0.6888 (5)	0.32749 (15)	0.0187 (6)
H6	0.4063	0.8108	0.2996	0.022*
C7	0.84829 (18)	0.3891 (5)	0.38745 (16)	0.0202 (6)
C8	0.92115 (18)	0.2283 (6)	0.43640 (17)	0.0247 (6)
H8A	0.8971	0.0522	0.4445	0.030*
H8B	0.9378	0.3070	0.4904	0.030*
C9	1.00726 (19)	0.2246 (5)	0.38442 (17)	0.0252 (6)
H9A	1.0673	0.2150	0.4193	0.030*
H9B	1.0041	0.0767	0.3464	0.030*
C10	1.00007 (18)	0.4790 (5)	0.33771 (17)	0.0248 (6)
H10A	1.0339	0.4684	0.2870	0.030*
H10B	1.0275	0.6213	0.3717	0.030*
C11	0.89299 (18)	0.5202 (5)	0.31788 (16)	0.0220 (6)
H11A	0.8771	0.7055	0.3160	0.026*
H11B	0.8718	0.4405	0.2650	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0185 (3)	0.0147 (3)	0.0246 (4)	−0.0019 (3)	0.0025 (3)	−0.0034 (3)
O1	0.0247 (11)	0.0141 (9)	0.0531 (15)	−0.0038 (8)	0.0079 (10)	−0.0002 (9)
O2	0.0233 (10)	0.0373 (12)	0.0215 (10)	−0.0024 (9)	−0.0031 (8)	−0.0091 (9)
N1	0.0220 (12)	0.0134 (11)	0.0203 (13)	0.0014 (9)	0.0032 (10)	0.0016 (10)
N2	0.0204 (12)	0.0261 (13)	0.0255 (13)	0.0024 (11)	0.0054 (9)	0.0109 (11)
N3	0.0200 (12)	0.0238 (12)	0.0191 (12)	0.0026 (10)	0.0003 (9)	0.0055 (10)
C1	0.0169 (13)	0.0186 (13)	0.0162 (13)	−0.0002 (10)	0.0021 (10)	−0.0031 (10)
C2	0.0242 (14)	0.0160 (13)	0.0180 (14)	−0.0013 (11)	0.0063 (11)	0.0008 (11)
C3	0.0232 (14)	0.0176 (13)	0.0189 (14)	0.0024 (11)	0.0014 (11)	0.0027 (11)
C4	0.0187 (13)	0.0201 (13)	0.0162 (13)	−0.0010 (11)	0.0029 (10)	−0.0026 (11)
C5	0.0229 (14)	0.0166 (13)	0.0189 (14)	−0.0014 (11)	0.0050 (11)	0.0004 (11)
C6	0.0230 (14)	0.0154 (12)	0.0175 (13)	0.0016 (11)	0.0001 (10)	−0.0009 (11)
C7	0.0201 (14)	0.0214 (14)	0.0190 (14)	−0.0013 (11)	−0.0006 (10)	0.0003 (11)
C8	0.0210 (14)	0.0310 (15)	0.0218 (15)	0.0034 (12)	−0.0003 (11)	0.0083 (12)
C9	0.0239 (15)	0.0278 (15)	0.0237 (15)	0.0043 (12)	0.0009 (11)	0.0027 (12)
C10	0.0179 (14)	0.0315 (16)	0.0248 (15)	0.0021 (12)	0.0003 (11)	0.0053 (12)
C11	0.0191 (14)	0.0257 (15)	0.0211 (14)	−0.0011 (11)	0.0009 (11)	0.0058 (12)

Geometric parameters (Å, º) top

S1—O2	1.4444 (19)	C5—C6	1.377 (4)
S1—O1	1.4430 (19)	C5—H5	0.9500
S1—N1	1.606 (2)	C6—H6	0.9500
S1—C1	1.760 (3)	C7—C8	1.513 (4)
N1—H1	0.878 (10)	C7—C11	1.507 (3)
N1—H2	0.879 (10)	C8—C9	1.534 (4)
N2—N3	1.379 (3)	C8—H8A	0.9900
N2—C4	1.383 (3)	C8—H8B	0.9900
N2—H3	0.875 (10)	C9—C10	1.530 (4)
N3—C7	1.281 (3)	C9—H9A	0.9900
C1—C2	1.391 (4)	C9—H9B	0.9900
C1—C6	1.400 (4)	C10—C11	1.539 (3)
C2—C3	1.388 (4)	C10—H10A	0.9900
C2—H2A	0.9500	C10—H10B	0.9900
C3—C4	1.403 (4)	C11—H11A	0.9900
C3—H3A	0.9500	C11—H11B	0.9900
C4—C5	1.401 (4)

O2—S1—O1	118.77 (12)	C5—C6—H6	120.1
O2—S1—N1	106.95 (12)	C1—C6—H6	120.1
O1—S1—N1	106.37 (12)	N3—C7—C8	120.7 (2)
O2—S1—C1	106.97 (12)	N3—C7—C11	128.9 (2)
O1—S1—C1	107.43 (12)	C8—C7—C11	110.4 (2)
N1—S1—C1	110.25 (12)	C7—C8—C9	104.3 (2)
S1—N1—H1	117.4 (19)	C7—C8—H8A	110.9
S1—N1—H2	111 (2)	C9—C8—H8A	110.9
H1—N1—H2	113 (3)	C7—C8—H8B	110.9
N3—N2—C4	119.4 (2)	C9—C8—H8B	110.9
N3—N2—H3	119.8 (19)	H8A—C8—H8B	108.9
C4—N2—H3	120.8 (19)	C10—C9—C8	103.9 (2)
C7—N3—N2	117.3 (2)	C10—C9—H9A	111.0
C2—C1—C6	119.9 (2)	C8—C9—H9A	111.0
C2—C1—S1	121.1 (2)	C10—C9—H9B	111.0
C6—C1—S1	118.9 (2)	C8—C9—H9B	111.0
C3—C2—C1	120.5 (2)	H9A—C9—H9B	109.0
C3—C2—H2A	119.7	C9—C10—C11	104.9 (2)
C1—C2—H2A	119.7	C9—C10—H10A	110.8
C2—C3—C4	119.5 (2)	C11—C10—H10A	110.8
C2—C3—H3A	120.3	C9—C10—H10B	110.8
C4—C3—H3A	120.3	C11—C10—H10B	110.8
N2—C4—C5	118.2 (2)	H10A—C10—H10B	108.9
N2—C4—C3	122.1 (2)	C7—C11—C10	103.5 (2)
C5—C4—C3	119.6 (2)	C7—C11—H11A	111.1
C6—C5—C4	120.6 (2)	C10—C11—H11A	111.1
C6—C5—H5	119.7	C7—C11—H11B	111.1
C4—C5—H5	119.7	C10—C11—H11B	111.1
C5—C6—C1	119.8 (2)	H11A—C11—H11B	109.0

C4—N2—N3—C7	165.4 (2)	N2—C4—C5—C6	175.1 (2)
O2—S1—C1—C2	−133.3 (2)	C3—C4—C5—C6	−2.9 (4)
O1—S1—C1—C2	−4.8 (2)	C4—C5—C6—C1	0.9 (4)
N1—S1—C1—C2	110.7 (2)	C2—C1—C6—C5	1.7 (4)
O2—S1—C1—C6	42.8 (2)	S1—C1—C6—C5	−174.46 (19)
O1—S1—C1—C6	171.4 (2)	N2—N3—C7—C8	177.6 (2)
N1—S1—C1—C6	−73.1 (2)	N2—N3—C7—C11	−2.2 (4)
C6—C1—C2—C3	−2.4 (4)	N3—C7—C8—C9	169.5 (3)
S1—C1—C2—C3	173.71 (19)	C11—C7—C8—C9	−10.6 (3)
C1—C2—C3—C4	0.4 (4)	C7—C8—C9—C10	28.9 (3)
N3—N2—C4—C5	173.1 (2)	C8—C9—C10—C11	−36.8 (3)
N3—N2—C4—C3	−8.9 (4)	N3—C7—C11—C10	168.0 (3)
C2—C3—C4—N2	−175.7 (2)	C8—C7—C11—C10	−11.8 (3)
C2—C3—C4—C5	2.3 (4)	C9—C10—C11—C7	29.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88 (1)	2.02 (1)	2.869 (3)	164 (3)
N1—H2···N3ⁱⁱ	0.88 (1)	2.13 (1)	2.993 (3)	166 (3)
N2—H3···O2ⁱⁱⁱ	0.88 (1)	2.36 (1)	3.220 (3)	166 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅N₃O₂S
M_r	253.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.1173 (14), 5.2038 (5), 16.4239 (19)
β (°)	94.019 (10)
V (Å³)	1203.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.35 × 0.05 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.914, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	4782, 2768, 2007
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.123, 1.03
No. of reflections	2768
No. of parameters	166
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.38

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88 (1)	2.02 (1)	2.869 (3)	164 (3)
N1—H2···N3ⁱⁱ	0.88 (1)	2.13 (1)	2.993 (3)	166 (3)
N2—H3···O2ⁱⁱⁱ	0.88 (1)	2.36 (1)	3.220 (3)	166 (3)

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

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors are grateful to the Center of Excellence for Advanced Materials Research and the Chemistry Department at King Abdulaziz University for providing the research facilities. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM.C/HIR/MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Al-Saadi, M. S., Rostom, S. A. F. & Faidallah, H. M. (2008). Arch. Pharm. Chem. Life Sci. 341, 181–190. CAS Google Scholar
Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2424. Web of Science CSD CrossRef IUCr Journals Google Scholar
Asiri, A. M., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o762–o763. CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals 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