N-Cyclohexyl-N-methylbenzene­sulfonamide

Haider, Z.; Khan, I.U.; Arshad, M.N.; Shafiq, M.; Niu, C.

doi:10.1107/S1600536809041762

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2892

https://doi.org/10.1107/S1600536809041762

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N-Cyclohexyl-N-methylbenzenesulfonamide

Zeeshan Haider,^a Islam Ullah Khan,^a ^* Muhammad Nadeem Arshad,^a Muhammad Shafiq ^a and Caoyuan Niu ^b ^*

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: iukhan.gcu@gmail.com, niu_cy2000@yahoo.com.cn

(Received 9 October 2009; accepted 13 October 2009; online 28 October 2009)

The title compound, C₁₃H₁₉NO₂S, was synthesized by the reaction of N-cyclohexylaminebenzenesulfonamide and methyl iodide. The crystal packing is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

Compounds containing cyclohexylamine have been reported to be activators of dopamine receptors in the central nervous system, see: Hacksell et al. (1981 ). For related structures, see: Arshad et al. (2008 , 2009 ).

Experimental

Crystal data

C₁₃H₁₉NO₂S
M_r = 253.35
Monoclinic, P 2₁ /c
a = 9.2729 (5) Å
b = 12.1182 (7) Å
c = 12.5801 (7) Å
β = 109.103 (2)°
V = 1335.79 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.28 × 0.12 × 0.09 mm

Data collection

Bruker APEXII CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.938, T_max = 0.979
12741 measured reflections
2489 independent reflections
1864 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.113
S = 1.08
2489 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.93	2.52	3.268 (3)	137
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 and DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809041762/bt5092sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041762/bt5092Isup2.hkl

checkCIF report

Comment top

Sulfonamide compounds have gained much importance due to their therapeutic applications. The compound containing cyclohexylamine has been reported to be an activator of dopamine receptors in the CNS (Hacksell et al., 1981). The title compound is a sulfonamide derivative of cyclohexylamine in continuation to our previous work (Arshad et al., 2008; Arshad et al., 2009).

The molecular structure of the title compound (I) is shown in Fig. 1. The mean plane of the benzene ring and that of the four essentially planar C atoms (C8, C9, C11, C12. Maximum deviation, 0.0132 Å) of the chair-form cyclohexyl ring have a dihedral angle of 24.26 (9)°. Furthermore, there are intermolecular C—H···O hydrogen bonds between the aromatic H atom (H2) and one sulfonamide O atom (O2ⁱ, symmetric code: see table 1) of neighboring molecules that contribute to the three-dimensional packing (Fig. 2).

Related literature top

Compounds containing cyclohexylamine have been reported to

be activators of dopamine receptors in the central nervous system, see: Hacksell et al. (1981); For related structures, see: Arshad et al. (2008, 2009).

Experimental top

Sodium hydride (0.88 mmol) was taken in a round bottom flask and washed with n-hexane so as to remove the mineral oil dispersant. A solution of N-cyclohexylamine benzene sulfonamide (0.43 mmol) in 5 ml of N,N dimethyl formamide was added. The mixture was stirred for half an hour at room temperature. Then, methyl iodide (0.86 mmol) was added and stirring was continued for about 3 hrs until the complete consumption of sulfonamide. The reaction was monitored by TLC. After the completion of the reaction the contents were transferred into the distilled water ice. The product precipitated and was separated by filtration and recrystallized from methanol. The melting point of the product was observed to be 353 K uncorrected.

Structure description top

Compounds containing cyclohexylamine have been reported to

be activators of dopamine receptors in the central nervous system, see: Hacksell et al. (1981); For related structures, see: Arshad et al. (2008, 2009).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: 'SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Diagram showing the intermolecular hydrogen bonds (indicated by pink dashed lines).

N-Cyclohexyl-N-methylbenzenesulfonamide top

Crystal data top

C₁₃H₁₉NO₂S	F(000) = 544
M_r = 253.35	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3617 reflections
a = 9.2729 (5) Å	θ = 2.3–25.5°
b = 12.1182 (7) Å	µ = 0.23 mm⁻¹
c = 12.5801 (7) Å	T = 296 K
β = 109.103 (2)°	Block, colourless
V = 1335.79 (13) Å³	0.28 × 0.12 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD detector diffractometer	2489 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
phi and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→11
T_min = 0.938, T_max = 0.979	k = −14→14
12741 measured reflections	l = −13→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0559P)² + 0.2086P] where P = (F_o² + 2F_c²)/3
2489 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₃H₁₉NO₂S	V = 1335.79 (13) Å³
M_r = 253.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2729 (5) Å	µ = 0.23 mm⁻¹
b = 12.1182 (7) Å	T = 296 K
c = 12.5801 (7) Å	0.28 × 0.12 × 0.09 mm
β = 109.103 (2)°

Data collection top

Bruker APEXII CCD detector diffractometer	2489 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1864 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.979	R_int = 0.030
12741 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.08	Δρ_max = 0.16 e Å⁻³
2489 reflections	Δρ_min = −0.25 e Å⁻³
155 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
C1	0.67239 (19)	0.36402 (15)	0.21562 (15)	0.0443 (5)
C2	0.6576 (2)	0.33212 (18)	0.31729 (17)	0.0556 (5)
H2	0.7103	0.2710	0.3556	0.067*
C3	0.5644 (2)	0.3918 (2)	0.3605 (2)	0.0694 (7)
H3	0.5552	0.3717	0.4294	0.083*
C4	0.4849 (3)	0.4804 (2)	0.3038 (2)	0.0738 (7)
H4	0.4200	0.5192	0.3332	0.089*
C5	0.5005 (3)	0.51236 (19)	0.2034 (2)	0.0732 (7)
H5	0.4467	0.5731	0.1652	0.088*
C6	0.5951 (2)	0.45494 (17)	0.15921 (18)	0.0568 (5)
H6	0.6070	0.4772	0.0918	0.068*
C7	1.0474 (2)	0.29629 (15)	0.33830 (14)	0.0424 (4)
H7	0.9836	0.2401	0.3570	0.051*
C8	1.0716 (2)	0.38752 (18)	0.42469 (16)	0.0568 (5)
H8A	0.9739	0.4194	0.4203	0.068*
H8B	1.1338	0.4452	0.4084	0.068*
C9	1.1495 (2)	0.3434 (2)	0.54232 (16)	0.0632 (6)
H9A	1.1678	0.4037	0.5958	0.076*
H9B	1.0829	0.2907	0.5610	0.076*
C10	1.2988 (2)	0.2885 (2)	0.55192 (17)	0.0651 (6)
H10A	1.3416	0.2563	0.6262	0.078*
H10B	1.3701	0.3434	0.5430	0.078*
C11	1.2786 (3)	0.1995 (2)	0.46425 (18)	0.0679 (7)
H11A	1.2203	0.1392	0.4805	0.082*
H11B	1.3780	0.1710	0.4682	0.082*
C12	1.1976 (2)	0.24159 (18)	0.34615 (16)	0.0546 (5)
H12A	1.1787	0.1805	0.2936	0.065*
H12B	1.2625	0.2943	0.3255	0.065*
C13	1.0145 (3)	0.4353 (2)	0.18252 (19)	0.0719 (7)
H13A	0.9857	0.4965	0.2197	0.108*
H13B	0.9659	0.4421	0.1027	0.108*
H13C	1.1233	0.4350	0.1996	0.108*
N1	0.96659 (17)	0.33232 (13)	0.22141 (13)	0.0485 (4)
O1	0.78750 (17)	0.17730 (12)	0.18902 (14)	0.0710 (5)
O2	0.75416 (18)	0.32058 (15)	0.04381 (11)	0.0769 (5)
S1	0.79429 (6)	0.29004 (4)	0.15969 (4)	0.0523 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0369 (9)	0.0421 (11)	0.0442 (10)	−0.0061 (8)	0.0002 (7)	−0.0009 (8)
C2	0.0458 (11)	0.0601 (14)	0.0563 (12)	−0.0031 (10)	0.0104 (9)	0.0119 (10)
C3	0.0505 (12)	0.0910 (19)	0.0690 (15)	−0.0087 (13)	0.0227 (11)	−0.0028 (13)
C4	0.0447 (12)	0.0776 (18)	0.098 (2)	−0.0046 (12)	0.0213 (13)	−0.0252 (15)
C5	0.0569 (14)	0.0515 (14)	0.098 (2)	0.0069 (11)	0.0078 (13)	0.0027 (13)
C6	0.0513 (12)	0.0506 (13)	0.0579 (12)	0.0002 (10)	0.0033 (10)	0.0078 (10)
C7	0.0397 (10)	0.0442 (11)	0.0410 (10)	−0.0014 (8)	0.0101 (8)	0.0003 (8)
C8	0.0558 (12)	0.0591 (13)	0.0535 (12)	0.0128 (10)	0.0151 (9)	−0.0100 (10)
C9	0.0655 (14)	0.0758 (16)	0.0468 (12)	0.0075 (11)	0.0163 (10)	−0.0124 (10)
C10	0.0573 (13)	0.0805 (17)	0.0477 (12)	0.0090 (11)	0.0039 (10)	−0.0097 (11)
C11	0.0618 (14)	0.0700 (16)	0.0583 (13)	0.0212 (11)	0.0009 (10)	−0.0093 (11)
C12	0.0519 (12)	0.0567 (13)	0.0507 (12)	0.0091 (9)	0.0108 (9)	−0.0131 (9)
C13	0.0738 (15)	0.0693 (16)	0.0675 (15)	−0.0071 (12)	0.0162 (12)	0.0176 (12)
N1	0.0454 (9)	0.0507 (10)	0.0462 (9)	−0.0010 (7)	0.0108 (7)	0.0024 (7)
O1	0.0658 (10)	0.0425 (9)	0.0905 (11)	−0.0052 (7)	0.0064 (8)	−0.0131 (8)
O2	0.0797 (11)	0.1027 (13)	0.0379 (8)	0.0063 (9)	0.0050 (7)	−0.0119 (8)
S1	0.0513 (3)	0.0512 (3)	0.0449 (3)	−0.0004 (2)	0.0027 (2)	−0.0090 (2)

Geometric parameters (Å, º) top

C1—C6	1.378 (3)	C9—C10	1.505 (3)
C1—C2	1.385 (3)	C9—H9A	0.9700
C1—S1	1.760 (2)	C9—H9B	0.9700
C2—C3	1.369 (3)	C10—C11	1.509 (3)
C2—H2	0.9300	C10—H10A	0.9700
C3—C4	1.364 (3)	C10—H10B	0.9700
C3—H3	0.9300	C11—C12	1.517 (3)
C4—C5	1.374 (4)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—C6	1.372 (3)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
C6—H6	0.9300	C13—N1	1.462 (3)
C7—N1	1.481 (2)	C13—H13A	0.9600
C7—C8	1.515 (3)	C13—H13B	0.9600
C7—C12	1.516 (3)	C13—H13C	0.9600
C7—H7	0.9800	N1—S1	1.6144 (16)
C8—C9	1.516 (3)	O1—S1	1.4218 (16)
C8—H8A	0.9700	O2—S1	1.4302 (15)
C8—H8B	0.9700

C6—C1—C2	120.5 (2)	H9A—C9—H9B	108.0
C6—C1—S1	119.68 (16)	C9—C10—C11	111.51 (18)
C2—C1—S1	119.84 (15)	C9—C10—H10A	109.3
C3—C2—C1	119.1 (2)	C11—C10—H10A	109.3
C3—C2—H2	120.5	C9—C10—H10B	109.3
C1—C2—H2	120.5	C11—C10—H10B	109.3
C4—C3—C2	120.8 (2)	H10A—C10—H10B	108.0
C4—C3—H3	119.6	C10—C11—C12	112.27 (18)
C2—C3—H3	119.6	C10—C11—H11A	109.2
C3—C4—C5	120.1 (2)	C12—C11—H11A	109.1
C3—C4—H4	120.0	C10—C11—H11B	109.1
C5—C4—H4	120.0	C12—C11—H11B	109.1
C6—C5—C4	120.2 (2)	H11A—C11—H11B	107.9
C6—C5—H5	119.9	C11—C12—C7	111.14 (17)
C4—C5—H5	119.9	C11—C12—H12A	109.4
C5—C6—C1	119.4 (2)	C7—C12—H12A	109.4
C5—C6—H6	120.3	C11—C12—H12B	109.4
C1—C6—H6	120.3	C7—C12—H12B	109.4
N1—C7—C8	113.90 (15)	H12A—C12—H12B	108.0
N1—C7—C12	110.43 (15)	N1—C13—H13A	109.5
C8—C7—C12	110.80 (15)	N1—C13—H13B	109.5
N1—C7—H7	107.1	H13A—C13—H13B	109.5
C8—C7—H7	107.1	N1—C13—H13C	109.5
C12—C7—H7	107.1	H13A—C13—H13C	109.5
C7—C8—C9	110.76 (17)	H13B—C13—H13C	109.5
C7—C8—H8A	109.5	C13—N1—C7	118.27 (15)
C9—C8—H8A	109.5	C13—N1—S1	118.12 (13)
C7—C8—H8B	109.5	C7—N1—S1	118.92 (12)
C9—C8—H8B	109.5	O1—S1—O2	119.63 (10)
H8A—C8—H8B	108.1	O1—S1—N1	107.52 (9)
C10—C9—C8	111.50 (17)	O2—S1—N1	107.13 (10)
C10—C9—H9A	109.3	O1—S1—C1	107.27 (10)
C8—C9—H9A	109.3	O2—S1—C1	106.79 (9)
C10—C9—H9B	109.3	N1—S1—C1	108.06 (8)
C8—C9—H9B	109.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.52	3.268 (3)	137

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₉NO₂S
M_r	253.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.2729 (5), 12.1182 (7), 12.5801 (7)
β (°)	109.103 (2)
V (Å³)	1335.79 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.28 × 0.12 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.938, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	12741, 2489, 1864
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.113, 1.08
No. of reflections	2489
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.25

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 'SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.52	3.268 (3)	137

Symmetry code: (i) x, −y+1/2, z+1/2.

References

Arshad, M. N., Tahir, M. N., Khan, I. U., Ahmad, E. & Shafiq, M. (2008). Acta Cryst. E64, o2380. Web of Science CSD CrossRef IUCr Journals Google Scholar
Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Ahmad, S. (2009). Acta Cryst. E65, o940. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR. Bonn, Germany. Google Scholar
Bruker (2005). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hacksell, U., Arvidsson, L.-E., Svensson, U., Nilsson, J. L. G., Sanchez, D., Wikstroem, H., Lindberg, P., Hjorth, S. & Carlsson, A. (1981). J. Med. Chem. 24, 1475–1482. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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