4-{2-[(E)-Cyclo-pentyl-idene]hydrazin-1-yl}benzene-sulfonamide.

The title mol-ecule, C(11)H(15)N(3)O(2)S, features a five-membered ring which is twisted about the middle CH(2)-CH(2) bond. The benzene ring is inclined with respect to the imine residue [C-N-N-C torsion angle = 165.4 (2)°]. Supra-molecular 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 inter-molecular inter-action 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 = 253.32

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.123

S = 1.03

2768 reflections

166 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.38 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012524/jj2126sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H15N3O2S	F(000) = 536
Mr = 253.32	Dx = 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

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	Rint = 0.044
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.5°
ω scan	h = −18→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −4→6
Tmin = 0.914, Tmax = 0.995	l = −21→21
4782 measured reflections

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(Fo2) + (0.0372P)2 + 0.8414P] where P = (Fo2 + 2Fc2)/3
2768 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.32 e Å−3
3 restraints	Δρmin = −0.38 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) ; (ii) ; (iii) .