N-Cyclo­hexyl-N-propyl­benzene­sulfonamide

Haider, Z.; Khan, I.U.; Zia-ur-Rehman, M.; Arshad, M.N.

doi:10.1107/S1600536809046650

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3165

doi:10.1107/S1600536809046650

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N-Cyclohexyl-N-propylbenzenesulfonamide

Zeeshan Haider,^a Islam Ullah Khan,^a ^* Muhammad Zia-ur-Rehman ^b and Muhammad Nadeem Arshad ^a

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Ferozpure Road, Lahore 54600, Pakistan
^*Correspondence e-mail: iukhan.gcu@gmail.com

(Received 2 November 2009; accepted 5 November 2009; online 21 November 2009)

The title compound, C₁₅H₂₃NO₂S, synthesized by N-methylation of cyclohexylamine sulfonamide with propyl iodide, is of interest as a precursor to biologically active sulfur-containing heterocyclic compounds. The cyclohexyl ring exists in the chair form and the dihedral angle between the ring plane of the benzene ring and that of the cyclohexyl ring is 50.13 (9)°.

Related literature

For the synthesis of related molecules, see: Kayser et al. (2004 ); Zia-ur-Rehman et al. (2006 , 2009 ). For the biological activity of sulfonamides, see: La Roche & Co (1967 ); Rough et al. (1998 ); Gennarti et al. (1994 ). For related structures, see: Arshad et al. (2008 ); Khan et al. (2009 ); Gowda et al. (2007a ,b ,c ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₂₃NO₂S
M_r = 281.40
Monoclinic, P 2₁ /n
a = 8.5532 (3) Å
b = 11.6877 (4) Å
c = 15.4410 (5) Å
β = 90.649 (2)°
V = 1543.50 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.42 × 0.31 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.918, T_max = 0.950
17345 measured reflections
3839 independent reflections
2475 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.141
S = 1.03
3839 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046650/hg2581sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046650/hg2581Isup2.hkl

checkCIF report

Comment top

Sulfonamides are well known for their enormous potential as biologically active molecules (Rough et al., 1998). They are being used as anti-microbial (Kayser et al., 2004), anti-convulsant (Arshad et al., 2008), anti-cancer (La Roche & Co, 1967) agents and for the treatment of inflammatory rheumatic and non-rheumatic processes including onsets and traumatologic lesions (Gennarti et al., 1994). In the present paper, the structure of N-cyclohexyl-N-propyl benzene sulfonamide has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing heterocyclic compounds (Zia-ur-Rehman et al., 2006, 2009; Khan et al., 2009). In the molecule of (I) (Scheme 1; Fig. 1), bond lengths and bond angles are almost similar to those in the related molecules (Gowda et al., 2007a,b,c) and are within normal ranges (Allen et al., 1987). The benzene ring is essentially planar while cyclohexane ring is in chair form. No significant hydrogen bond interactions are observed in the title molecule. The dihedral angle between the phenyl and cyclohexane rings is 50.13 (9)%.

Related literature top

For the synthesis of related molecules, see: Kayser et al. (2004); Zia-ur-Rehman et al. (2006, 2009). For the biological activity of sulfonamides, see: La Roche & Co (1967); Rough et al. (1998); Gennarti et al. (1994). For related structures, see: Arshad et al. (2008); Khan et al. (2009); Gowda et al. (2007a,b,c). For bond-length data, see: Allen et al. (1987);

Experimental top

A mixture of N-cyclohexylbenzene sulfonamide (1 g, 0.43 mmol), sodium hydride (0.21 g; 0.88 mmoles) and N, N-dimethylformamide (10.0 ml) was stirred at room temperature for half an hour followed by addition of propyl iodide (0.146 g; 0.86 mmoles). Stirring was continued further for a period of three hours and the contents were poured over crushed ice. Precipitated product was isolated, washed and crystallized from methanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 50% probability level.

N-Cyclohexyl-N-propylbenzenesulfonamide top

Crystal data top

C₁₅H₂₃NO₂S	F(000) = 608
M_r = 281.40	D_x = 1.211 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4904 reflections
a = 8.5532 (3) Å	θ = 2.2–24.1°
b = 11.6877 (4) Å	µ = 0.21 mm⁻¹
c = 15.4410 (5) Å	T = 296 K
β = 90.649 (2)°	Needles, colourless
V = 1543.50 (9) Å³	0.42 × 0.31 × 0.25 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3839 independent reflections
Radiation source: fine-focus sealed tube	2475 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
T_min = 0.918, T_max = 0.950	k = −15→15
17345 measured reflections	l = −20→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0648P)² + 0.2752P] where P = (F_o² + 2F_c²)/3
3839 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₂₃NO₂S	V = 1543.50 (9) Å³
M_r = 281.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.5532 (3) Å	µ = 0.21 mm⁻¹
b = 11.6877 (4) Å	T = 296 K
c = 15.4410 (5) Å	0.42 × 0.31 × 0.25 mm
β = 90.649 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3839 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2475 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.950	R_int = 0.041
17345 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
3839 reflections	Δρ_min = −0.21 e Å⁻³
173 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
S1	0.25538 (5)	0.86234 (4)	0.23201 (4)	0.05546 (19)
O1	0.36858 (17)	0.78724 (15)	0.26990 (10)	0.0777 (5)
O2	0.29533 (18)	0.97863 (13)	0.21357 (12)	0.0803 (5)
N1	0.10568 (17)	0.86333 (13)	0.29521 (10)	0.0483 (4)
C1	0.1958 (2)	0.80108 (17)	0.13244 (12)	0.0480 (4)
C2	0.1431 (3)	0.8704 (2)	0.06558 (16)	0.0702 (6)
H2	0.1435	0.9495	0.0718	0.084*
C3	0.0896 (3)	0.8205 (3)	−0.01092 (16)	0.0908 (9)
H3	0.0530	0.8666	−0.0559	0.109*
C4	0.0904 (3)	0.7056 (3)	−0.02042 (18)	0.0919 (9)
H4	0.0546	0.6731	−0.0719	0.110*
C5	0.1431 (3)	0.6373 (2)	0.04474 (18)	0.0800 (7)
H5	0.1438	0.5584	0.0373	0.096*
C6	0.1956 (2)	0.68386 (18)	0.12180 (14)	0.0579 (5)
H6	0.2307	0.6365	0.1664	0.070*
C7	−0.01977 (19)	0.94843 (16)	0.27965 (11)	0.0458 (4)
H7	0.0252	1.0101	0.2449	0.055*
C8	−0.0737 (2)	1.00139 (17)	0.36414 (12)	0.0535 (5)
H8A	−0.1183	0.9425	0.4006	0.064*
H8B	0.0154	1.0342	0.3947	0.064*
C9	−0.1949 (3)	1.09394 (19)	0.34699 (16)	0.0680 (6)
H9A	−0.2317	1.1236	0.4018	0.082*
H9B	−0.1467	1.1565	0.3157	0.082*
C10	−0.3316 (2)	1.0492 (2)	0.29526 (14)	0.0630 (6)
H10A	−0.4030	1.1116	0.2825	0.076*
H10B	−0.3871	0.9929	0.3293	0.076*
C11	−0.2801 (3)	0.9953 (2)	0.21182 (14)	0.0703 (6)
H11A	−0.2348	1.0533	0.1749	0.084*
H11B	−0.3702	0.9632	0.1818	0.084*
C12	−0.1603 (2)	0.9014 (2)	0.22887 (14)	0.0613 (6)
H12A	−0.1255	0.8701	0.1742	0.074*
H12B	−0.2084	0.8401	0.2615	0.074*
C13	0.0697 (2)	0.75885 (17)	0.34458 (13)	0.0545 (5)
H13A	0.1140	0.6935	0.3149	0.065*
H13B	−0.0428	0.7487	0.3456	0.065*
C14	0.1314 (3)	0.7611 (2)	0.43649 (16)	0.0804 (7)
H14A	0.2445	0.7669	0.4357	0.097*
H14B	0.0914	0.8284	0.4655	0.097*
C15	0.0861 (4)	0.6566 (2)	0.48662 (18)	0.0980 (9)
H15A	−0.0250	0.6564	0.4950	0.147*
H15B	0.1385	0.6571	0.5419	0.147*
H15C	0.1157	0.5894	0.4551	0.147*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0365 (3)	0.0626 (3)	0.0673 (4)	−0.0039 (2)	0.0035 (2)	−0.0127 (3)
O1	0.0456 (8)	0.1083 (13)	0.0789 (11)	0.0169 (8)	−0.0108 (7)	−0.0136 (9)
O2	0.0622 (9)	0.0621 (10)	0.1173 (13)	−0.0246 (7)	0.0279 (9)	−0.0219 (9)
N1	0.0423 (8)	0.0550 (9)	0.0477 (9)	0.0016 (7)	0.0022 (7)	−0.0050 (7)
C1	0.0392 (9)	0.0537 (11)	0.0514 (11)	0.0011 (8)	0.0112 (8)	0.0023 (9)
C2	0.0690 (15)	0.0709 (15)	0.0711 (16)	0.0122 (11)	0.0181 (12)	0.0127 (12)
C3	0.0806 (18)	0.140 (3)	0.0521 (15)	0.0295 (18)	0.0081 (12)	0.0178 (16)
C4	0.0700 (16)	0.142 (3)	0.0642 (17)	0.0134 (18)	0.0044 (13)	−0.0290 (18)
C5	0.0737 (17)	0.0819 (17)	0.0847 (19)	−0.0037 (13)	0.0127 (14)	−0.0285 (15)
C6	0.0567 (12)	0.0565 (12)	0.0607 (13)	0.0038 (9)	0.0086 (10)	−0.0045 (10)
C7	0.0402 (9)	0.0529 (11)	0.0444 (10)	−0.0004 (8)	0.0011 (7)	−0.0036 (8)
C8	0.0516 (11)	0.0602 (12)	0.0485 (11)	0.0030 (9)	−0.0064 (8)	−0.0130 (9)
C9	0.0713 (15)	0.0626 (13)	0.0702 (14)	0.0163 (11)	0.0034 (11)	−0.0114 (11)
C10	0.0527 (12)	0.0780 (14)	0.0584 (13)	0.0185 (10)	0.0022 (10)	0.0054 (11)
C11	0.0524 (12)	0.1059 (19)	0.0525 (12)	0.0112 (12)	−0.0068 (10)	0.0014 (12)
C12	0.0464 (11)	0.0857 (15)	0.0518 (12)	0.0056 (10)	−0.0062 (9)	−0.0209 (11)
C13	0.0507 (11)	0.0565 (12)	0.0564 (12)	0.0007 (9)	−0.0040 (9)	−0.0079 (9)
C14	0.0900 (18)	0.0855 (17)	0.0652 (15)	0.0007 (14)	−0.0233 (13)	0.0073 (13)
C15	0.119 (2)	0.095 (2)	0.0801 (18)	0.0125 (17)	0.0040 (17)	0.0243 (15)

Geometric parameters (Å, º) top

S1—O1	1.4274 (16)	C8—H8B	0.9700
S1—O2	1.4308 (16)	C9—C10	1.502 (3)
S1—N1	1.6187 (15)	C9—H9A	0.9700
S1—C1	1.7658 (19)	C9—H9B	0.9700
N1—C13	1.474 (2)	C10—C11	1.504 (3)
N1—C7	1.481 (2)	C10—H10A	0.9700
C1—C6	1.380 (3)	C10—H10B	0.9700
C1—C2	1.384 (3)	C11—C12	1.522 (3)
C2—C3	1.390 (4)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.351 (4)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.357 (4)	C13—C14	1.509 (3)
C4—H4	0.9300	C13—H13A	0.9700
C5—C6	1.379 (3)	C13—H13B	0.9700
C5—H5	0.9300	C14—C15	1.499 (3)
C6—H6	0.9300	C14—H14A	0.9700
C7—C8	1.520 (2)	C14—H14B	0.9700
C7—C12	1.530 (2)	C15—H15A	0.9600
C7—H7	0.9800	C15—H15B	0.9600
C8—C9	1.520 (3)	C15—H15C	0.9600
C8—H8A	0.9700

O1—S1—O2	120.22 (11)	C8—C9—H9A	109.3
O1—S1—N1	107.15 (9)	C10—C9—H9B	109.3
O2—S1—N1	107.79 (9)	C8—C9—H9B	109.3
O1—S1—C1	107.16 (9)	H9A—C9—H9B	107.9
O2—S1—C1	106.21 (10)	C9—C10—C11	111.57 (18)
N1—S1—C1	107.79 (8)	C9—C10—H10A	109.3
C13—N1—C7	119.02 (15)	C11—C10—H10A	109.3
C13—N1—S1	118.51 (13)	C9—C10—H10B	109.3
C7—N1—S1	118.92 (12)	C11—C10—H10B	109.3
C6—C1—C2	119.5 (2)	H10A—C10—H10B	108.0
C6—C1—S1	120.41 (15)	C10—C11—C12	110.90 (17)
C2—C1—S1	120.04 (17)	C10—C11—H11A	109.5
C1—C2—C3	119.4 (2)	C12—C11—H11A	109.5
C1—C2—H2	120.3	C10—C11—H11B	109.5
C3—C2—H2	120.3	C12—C11—H11B	109.5
C4—C3—C2	120.5 (3)	H11A—C11—H11B	108.0
C4—C3—H3	119.8	C11—C12—C7	110.64 (17)
C2—C3—H3	119.8	C11—C12—H12A	109.5
C3—C4—C5	120.4 (3)	C7—C12—H12A	109.5
C3—C4—H4	119.8	C11—C12—H12B	109.5
C5—C4—H4	119.8	C7—C12—H12B	109.5
C4—C5—C6	120.7 (3)	H12A—C12—H12B	108.1
C4—C5—H5	119.7	N1—C13—C14	113.53 (17)
C6—C5—H5	119.7	N1—C13—H13A	108.9
C5—C6—C1	119.6 (2)	C14—C13—H13A	108.9
C5—C6—H6	120.2	N1—C13—H13B	108.9
C1—C6—H6	120.2	C14—C13—H13B	108.9
N1—C7—C8	111.13 (14)	H13A—C13—H13B	107.7
N1—C7—C12	113.91 (15)	C15—C14—C13	112.4 (2)
C8—C7—C12	110.00 (15)	C15—C14—H14A	109.1
N1—C7—H7	107.2	C13—C14—H14A	109.1
C8—C7—H7	107.2	C15—C14—H14B	109.1
C12—C7—H7	107.2	C13—C14—H14B	109.1
C9—C8—C7	110.68 (16)	H14A—C14—H14B	107.8
C9—C8—H8A	109.5	C14—C15—H15A	109.5
C7—C8—H8A	109.5	C14—C15—H15B	109.5
C9—C8—H8B	109.5	H15A—C15—H15B	109.5
C7—C8—H8B	109.5	C14—C15—H15C	109.5
H8A—C8—H8B	108.1	H15A—C15—H15C	109.5
C10—C9—C8	111.73 (18)	H15B—C15—H15C	109.5
C10—C9—H9A	109.3

O1—S1—N1—C13	−31.31 (16)	C2—C1—C6—C5	0.1 (3)
O2—S1—N1—C13	−162.01 (14)	S1—C1—C6—C5	177.52 (16)
C1—S1—N1—C13	83.73 (14)	C13—N1—C7—C8	64.7 (2)
O1—S1—N1—C7	170.12 (13)	S1—N1—C7—C8	−136.84 (14)
O2—S1—N1—C7	39.42 (16)	C13—N1—C7—C12	−60.2 (2)
C1—S1—N1—C7	−74.84 (15)	S1—N1—C7—C12	98.24 (17)
O1—S1—C1—C6	30.33 (18)	N1—C7—C8—C9	176.37 (16)
O2—S1—C1—C6	160.00 (15)	C12—C7—C8—C9	−56.5 (2)
N1—S1—C1—C6	−84.70 (16)	C7—C8—C9—C10	55.9 (2)
O1—S1—C1—C2	−152.24 (16)	C8—C9—C10—C11	−55.4 (3)
O2—S1—C1—C2	−22.57 (18)	C9—C10—C11—C12	55.7 (3)
N1—S1—C1—C2	92.73 (17)	C10—C11—C12—C7	−56.7 (3)
C6—C1—C2—C3	0.5 (3)	N1—C7—C12—C11	−177.24 (17)
S1—C1—C2—C3	−176.93 (17)	C8—C7—C12—C11	57.2 (2)
C1—C2—C3—C4	−0.6 (4)	C7—N1—C13—C14	−103.9 (2)
C2—C3—C4—C5	0.1 (4)	S1—N1—C13—C14	97.55 (19)
C3—C4—C5—C6	0.5 (4)	N1—C13—C14—C15	177.0 (2)
C4—C5—C6—C1	−0.6 (3)

Experimental details

Crystal data
Chemical formula	C₁₅H₂₃NO₂S
M_r	281.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.5532 (3), 11.6877 (4), 15.4410 (5)
β (°)	90.649 (2)
V (Å³)	1543.50 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.42 × 0.31 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.918, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	17345, 3839, 2475
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.141, 1.03
No. of reflections	3839
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for the financial support to purchase the diffractometer.

References

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