N-[4-(N-Cyclo­hexyl­sulfamo­yl)phen­yl]acetamide

Khan, I.U.; Akkurt, M.; Anwar, F.; Sharif, S.

doi:10.1107/S160053681000961X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages o868-o869

doi:10.1107/S160053681000961X

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N-[4-(N-Cyclohexylsulfamoyl)phenyl]acetamide

Islam Ullah Khan,^a ‡ Mehmet Akkurt,^b ^* Faiza Anwar ^a and Shahzad Sharif ^a

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 12 March 2010; accepted 14 March 2010; online 20 March 2010)

In the title compound, C₁₄H₂₀N₂O₃S, the cyclohexyl ring adopts a chair conformation: the four coplanar C atoms of this ring make a dihedral angle of 64.8 (2)° with the benzene ring. In the molecule, an intramolecular C—H⋯O contact generates an S(6) ring motif. In the crystal structure, molecules are linked via intermolecular N—H⋯O hydrogen bonds into two-dimensional layers propagating in (100).

Related literature

For related structures, see: Sharif et al. (2010 ); Mariam et al. (2009a ,b ); Asiri et al. (2009 ); Khan et al. (2009 ); Arshad et al. (2008 , 2009 ); Gowda et al. (2007a ,b ,c ); Haider et al. (2010 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₁₄H₂₀N₂O₃S
M_r = 296.39
Monoclinic, P 2₁ /c
a = 14.6929 (19) Å
b = 13.3486 (19) Å
c = 7.9769 (12) Å
β = 102.387 (7)°
V = 1528.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.32 × 0.09 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
11442 measured reflections
3628 independent reflections
1358 reflections with I > 2σ(I)
R_int = 0.110

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.218
S = 0.94
3628 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.30 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⋯O3ⁱ	0.86	2.07	2.862 (4)	153
N2—H2⋯O2ⁱⁱ	0.86	2.11	2.970 (4)	177
C9—H9⋯O3	0.93	2.28	2.866 (5)	120
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000961X/hb5359sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000961X/hb5359Isup2.hkl

checkCIF report

Comment top

The title compound (I), (Fig.1), was prepared and characterized as part of our ongoing studies of sulfonamide derivatives (Mariam et al., 2009a,b; Sharif et al., 2010).

The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to those in similar structures (Sharif et al., 2010; Mariam et al., 2009a,b; Asiri et al., 2009; Khan et al., 2009; Arshad et al., 2008; Gowda et al., 2007a,b,c; Haider et al., 2010).

The C1–C6 cyclohexyl ring of (I) adopts a classic chair conformation [puckering parameters (Cremer & Pople, 1975) Q_T = 0.559 (6) Å, θ = 180.0 (6) ° and ϕ = 212 (16) °]. Atoms C1 and C4 deviate by -0.667 (6)Å and 0.639 (4) Å, respectively, from the plane through the other four atoms (C2,C3, C5 and C6) of the cyclohexane ring. The dihedral angle between the benzene ring (C7–C12) and the C2/C3/C5/C6 least-squares plane of the cyclohexane ring is 64.76 (20)° (Nardelli, 1983).

In the molecule of (I), intramolecular C—H···O hydrogen contacts generate S(5) and S(6) ring motifs (Bernstein et al., 1995) (Table 1). In the crystal structure of (I), molecules are linked via intermolecular N—H···O hydrogen bonds into two-dimensional layers extended along the b axis (Table 1 and Fig. 2).

Related literature top

For related structures, see: Sharif et al. (2010); Mariam et al. (2009a,b); Asiri et al. (2009); Khan et al. (2009); Arshad et al. (2008, 2009); Gowda et al. (2007a,b,c); Haider et al. (2010). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

To 0.5 g ( 1.96 mmol ) N-acetyl p-amino sulfonyl chloride in 10 ml of distilled water was added 0.23 ml of cyclohexylamine (1.96 mmol) and stirring continued at room temperature, while maintaining the pH of the reaction mixture at 8 using 3% sodium carbonate. The progress of the reaction was continuously monitored by TLC. After consumption of all the reactants the mixture was filtered, dried and recrystalized from ethyl acetate to yield colourless needles of (I).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecule of (I) with displacement ellipsoids depicted at the 50% probability level for all non-H atoms.
	Fig. 2. The packing and hydrogen bonding of (I) viewed down a-axis. Hydrogen bonding is indicated by dashed lines. For clarity, H atoms not involved in hydrogen bonding are omitted.

N-[4-(N-Cyclohexylsulfamoyl)phenyl]acetamide top

Crystal data top

C₁₄H₂₀N₂O₃S	F(000) = 632
M_r = 296.39	D_x = 1.288 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1027 reflections
a = 14.6929 (19) Å	θ = 3.0–18.7°
b = 13.3486 (19) Å	µ = 0.22 mm⁻¹
c = 7.9769 (12) Å	T = 296 K
β = 102.387 (7)°	Needle, colourless
V = 1528.1 (4) Å³	0.32 × 0.09 × 0.06 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1358 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.110
Graphite monochromator	θ_max = 28.0°, θ_min = 1.4°
ϕ and ω scans	h = −19→16
11442 measured reflections	k = −17→16
3628 independent reflections	l = −10→9

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.218	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0926P)²] where P = (F_o² + 2F_c²)/3
3628 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₄H₂₀N₂O₃S	V = 1528.1 (4) Å³
M_r = 296.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.6929 (19) Å	µ = 0.22 mm⁻¹
b = 13.3486 (19) Å	T = 296 K
c = 7.9769 (12) Å	0.32 × 0.09 × 0.06 mm
β = 102.387 (7)°

Data collection top

Bruker APEXII CCD diffractometer	1358 reflections with I > 2σ(I)
11442 measured reflections	R_int = 0.110
3628 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.218	H-atom parameters constrained
S = 0.94	Δρ_max = 0.30 e Å⁻³
3628 reflections	Δρ_min = −0.38 e Å⁻³
182 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.68133 (8)	0.41022 (7)	0.21719 (15)	0.0554 (4)
O1	0.7323 (2)	0.3332 (2)	0.1552 (4)	0.0645 (11)
O2	0.6417 (2)	0.4904 (2)	0.1059 (4)	0.0679 (11)
O3	0.2838 (2)	0.3369 (2)	0.5231 (4)	0.0801 (15)
N1	0.7470 (2)	0.4618 (2)	0.3789 (5)	0.0619 (13)
N2	0.3647 (2)	0.2116 (2)	0.4351 (4)	0.0515 (11)
C1	0.9600 (4)	0.3914 (5)	0.8177 (8)	0.098 (3)
C2	0.9654 (3)	0.3437 (5)	0.6484 (8)	0.101 (3)
C3	0.9037 (3)	0.3989 (4)	0.4997 (7)	0.078 (2)
C4	0.8045 (3)	0.4037 (3)	0.5194 (6)	0.0537 (16)
C5	0.7987 (3)	0.4482 (4)	0.6899 (6)	0.0732 (19)
C6	0.8608 (4)	0.3946 (4)	0.8377 (7)	0.085 (2)
C7	0.5888 (3)	0.3520 (3)	0.2880 (5)	0.0468 (16)
C8	0.5176 (3)	0.4092 (3)	0.3263 (6)	0.0585 (16)
C9	0.4436 (3)	0.3657 (3)	0.3762 (6)	0.0553 (16)
C10	0.4389 (3)	0.2626 (3)	0.3903 (5)	0.0437 (12)
C11	0.5109 (3)	0.2061 (3)	0.3535 (5)	0.0488 (16)
C12	0.5852 (3)	0.2493 (3)	0.3041 (5)	0.0483 (16)
C13	0.2927 (3)	0.2488 (3)	0.4952 (5)	0.0533 (17)
C14	0.2223 (3)	0.1742 (4)	0.5213 (7)	0.0773 (19)
H1	0.74890	0.52610	0.38430	0.0750*
H1A	0.99740	0.35330	0.91120	0.1180*
H1B	0.98490	0.45900	0.82250	0.1180*
H2	0.36500	0.14760	0.42250	0.0620*
H2A	0.94580	0.27430	0.64800	0.1210*
H2B	1.02940	0.34490	0.63450	0.1210*
H3A	0.92720	0.46630	0.49340	0.0940*
H3B	0.90600	0.36490	0.39320	0.0940*
H4	0.77990	0.33530	0.51440	0.0650*
H5A	0.73470	0.44490	0.70360	0.0870*
H5B	0.81650	0.51820	0.69190	0.0870*
H6A	0.85800	0.42850	0.94400	0.1010*
H6B	0.83830	0.32670	0.84440	0.1010*
H8	0.52010	0.47860	0.31800	0.0700*
H9	0.39620	0.40550	0.40070	0.0660*
H11	0.50880	0.13670	0.36270	0.0580*
H12	0.63320	0.20960	0.28140	0.0580*
H14A	0.17610	0.20640	0.57140	0.1160*
H14B	0.25220	0.12230	0.59670	0.1160*
H14C	0.19300	0.14550	0.41280	0.1160*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0707 (8)	0.0406 (6)	0.0528 (8)	−0.0034 (6)	0.0085 (6)	0.0005 (6)
O1	0.083 (2)	0.0502 (16)	0.065 (2)	0.0036 (15)	0.0264 (17)	−0.0055 (15)
O2	0.089 (2)	0.0530 (17)	0.060 (2)	−0.0026 (16)	0.0121 (17)	0.0160 (16)
O3	0.111 (3)	0.0498 (19)	0.088 (3)	0.0200 (18)	0.040 (2)	−0.0019 (18)
N1	0.077 (2)	0.0364 (18)	0.064 (3)	−0.0082 (17)	−0.003 (2)	−0.0040 (18)
N2	0.064 (2)	0.0383 (18)	0.051 (2)	−0.0023 (18)	0.0095 (18)	−0.0030 (16)
C1	0.078 (4)	0.114 (5)	0.089 (5)	−0.001 (3)	−0.013 (3)	0.001 (4)
C2	0.059 (3)	0.135 (5)	0.104 (6)	0.014 (3)	0.009 (3)	−0.004 (4)
C3	0.064 (3)	0.103 (4)	0.068 (4)	−0.003 (3)	0.017 (3)	−0.006 (3)
C4	0.056 (3)	0.040 (2)	0.062 (3)	−0.002 (2)	0.006 (2)	−0.002 (2)
C5	0.083 (3)	0.070 (3)	0.069 (4)	0.005 (3)	0.022 (3)	−0.003 (3)
C6	0.102 (4)	0.095 (4)	0.055 (4)	0.015 (3)	0.012 (3)	0.005 (3)
C7	0.062 (3)	0.040 (2)	0.033 (3)	0.001 (2)	−0.002 (2)	−0.0018 (18)
C8	0.079 (3)	0.030 (2)	0.065 (3)	0.000 (2)	0.012 (3)	−0.002 (2)
C9	0.071 (3)	0.038 (2)	0.060 (3)	0.006 (2)	0.021 (2)	0.001 (2)
C10	0.058 (2)	0.038 (2)	0.029 (2)	0.002 (2)	−0.0040 (19)	−0.0041 (18)
C11	0.068 (3)	0.031 (2)	0.043 (3)	0.000 (2)	0.002 (2)	−0.0018 (19)
C12	0.063 (3)	0.036 (2)	0.044 (3)	0.003 (2)	0.007 (2)	−0.0042 (18)
C13	0.071 (3)	0.051 (3)	0.036 (3)	0.007 (2)	0.007 (2)	0.001 (2)
C14	0.077 (3)	0.079 (3)	0.081 (4)	−0.001 (3)	0.028 (3)	−0.002 (3)

Geometric parameters (Å, º) top

S1—O1	1.422 (3)	C11—C12	1.365 (6)
S1—O2	1.432 (3)	C13—C14	1.482 (7)
S1—N1	1.592 (4)	C1—H1A	0.9700
S1—C7	1.761 (4)	C1—H1B	0.9700
O3—C13	1.209 (5)	C2—H2A	0.9700
N1—C4	1.471 (6)	C2—H2B	0.9700
N2—C10	1.395 (5)	C3—H3A	0.9700
N2—C13	1.347 (5)	C3—H3B	0.9700
N1—H1	0.8600	C4—H4	0.9800
N2—H2	0.8600	C5—H5A	0.9700
C1—C6	1.501 (9)	C5—H5B	0.9700
C1—C2	1.511 (9)	C6—H6A	0.9700
C2—C3	1.520 (8)	C6—H6B	0.9700
C3—C4	1.501 (6)	C8—H8	0.9300
C4—C5	1.503 (7)	C9—H9	0.9300
C5—C6	1.508 (7)	C11—H11	0.9300
C7—C12	1.379 (6)	C12—H12	0.9300
C7—C8	1.381 (6)	C14—H14A	0.9600
C8—C9	1.365 (6)	C14—H14B	0.9600
C9—C10	1.384 (6)	C14—H14C	0.9600
C10—C11	1.381 (6)

O1—S1—O2	119.96 (19)	C1—C2—H2A	109.00
O1—S1—N1	108.76 (18)	C1—C2—H2B	109.00
O1—S1—C7	107.04 (18)	C3—C2—H2A	109.00
O2—S1—N1	105.91 (17)	C3—C2—H2B	109.00
O2—S1—C7	106.83 (19)	H2A—C2—H2B	108.00
N1—S1—C7	107.84 (19)	C2—C3—H3A	109.00
S1—N1—C4	122.6 (2)	C2—C3—H3B	109.00
C10—N2—C13	128.9 (3)	C4—C3—H3A	109.00
C4—N1—H1	119.00	C4—C3—H3B	109.00
S1—N1—H1	119.00	H3A—C3—H3B	108.00
C10—N2—H2	116.00	N1—C4—H4	108.00
C13—N2—H2	116.00	C3—C4—H4	108.00
C2—C1—C6	110.2 (5)	C5—C4—H4	108.00
C1—C2—C3	110.9 (5)	C4—C5—H5A	109.00
C2—C3—C4	111.7 (4)	C4—C5—H5B	109.00
N1—C4—C5	110.3 (4)	C6—C5—H5A	109.00
C3—C4—C5	110.9 (4)	C6—C5—H5B	109.00
N1—C4—C3	110.8 (4)	H5A—C5—H5B	108.00
C4—C5—C6	112.2 (4)	C1—C6—H6A	109.00
C1—C6—C5	111.7 (5)	C1—C6—H6B	109.00
C8—C7—C12	118.9 (4)	C5—C6—H6A	109.00
S1—C7—C8	120.0 (3)	C5—C6—H6B	109.00
S1—C7—C12	121.1 (3)	H6A—C6—H6B	108.00
C7—C8—C9	121.2 (4)	C7—C8—H8	119.00
C8—C9—C10	120.2 (4)	C9—C8—H8	119.00
N2—C10—C9	124.2 (4)	C8—C9—H9	120.00
N2—C10—C11	117.7 (3)	C10—C9—H9	120.00
C9—C10—C11	118.2 (4)	C10—C11—H11	119.00
C10—C11—C12	121.8 (4)	C12—C11—H11	119.00
C7—C12—C11	119.7 (4)	C7—C12—H12	120.00
O3—C13—C14	121.4 (4)	C11—C12—H12	120.00
N2—C13—C14	115.3 (4)	C13—C14—H14A	110.00
O3—C13—N2	123.3 (4)	C13—C14—H14B	109.00
C2—C1—H1A	110.00	C13—C14—H14C	109.00
C2—C1—H1B	110.00	H14A—C14—H14B	109.00
C6—C1—H1A	110.00	H14A—C14—H14C	109.00
C6—C1—H1B	110.00	H14B—C14—H14C	109.00
H1A—C1—H1B	108.00

O1—S1—N1—C4	−46.6 (4)	C1—C2—C3—C4	−56.3 (6)
O2—S1—N1—C4	−176.8 (3)	C2—C3—C4—N1	177.1 (4)
C7—S1—N1—C4	69.2 (4)	C2—C3—C4—C5	54.4 (6)
O1—S1—C7—C8	−168.3 (3)	N1—C4—C5—C6	−176.8 (4)
O1—S1—C7—C12	10.9 (4)	C3—C4—C5—C6	−53.8 (5)
O2—S1—C7—C8	−38.6 (4)	C4—C5—C6—C1	55.2 (6)
O2—S1—C7—C12	140.5 (3)	S1—C7—C8—C9	177.9 (4)
N1—S1—C7—C8	74.8 (4)	C12—C7—C8—C9	−1.3 (7)
N1—S1—C7—C12	−106.0 (3)	S1—C7—C12—C11	−177.7 (3)
S1—N1—C4—C3	100.2 (4)	C8—C7—C12—C11	1.5 (6)
S1—N1—C4—C5	−136.7 (3)	C7—C8—C9—C10	0.4 (7)
C13—N2—C10—C9	−10.3 (6)	C8—C9—C10—N2	−177.9 (4)
C13—N2—C10—C11	171.5 (4)	C8—C9—C10—C11	0.3 (6)
C10—N2—C13—O3	−1.7 (7)	N2—C10—C11—C12	178.3 (4)
C10—N2—C13—C14	176.7 (4)	C9—C10—C11—C12	−0.1 (6)
C6—C1—C2—C3	56.5 (6)	C10—C11—C12—C7	−0.8 (6)
C2—C1—C6—C5	−56.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.07	2.862 (4)	153
N2—H2···O2ⁱⁱ	0.86	2.11	2.970 (4)	177
C9—H9···O3	0.93	2.28	2.866 (5)	120

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

Experimental details

Crystal data
Chemical formula	C₁₄H₂₀N₂O₃S
M_r	296.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.6929 (19), 13.3486 (19), 7.9769 (12)
β (°)	102.387 (7)
V (Å³)	1528.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.32 × 0.09 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11442, 3628, 1358
R_int	0.110
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.218, 0.94
No. of reflections	3628
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.38

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.07	2.862 (4)	153
N2—H2···O2ⁱⁱ	0.86	2.11	2.970 (4)	177
C9—H9···O3	0.93	2.28	2.866 (5)	120

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

Footnotes

‡Additional corresponding author, e-mail: iuklodhi@yahoo.com.

Acknowledgements

The authors are grateful to the Campus Engineer GCUL, Mr Bilal Ahmad, for providing support services at the Materials Chemistry Laboratory.

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