N,N-Dicyclo­hexyl-4-nitro­benzamide

Sohail Saeed; Naghmana Rashid; Ray J Butcher; Sema Öztürk Yildirim; Rizwan Hussain

doi:10.1107/S1600536812035660

. 2012 Aug 25;68(Pt 9):o2762. doi: 10.1107/S1600536812035660

N,N-Dicyclohexyl-4-nitrobenzamide

Sohail Saeed ^a,^*, Naghmana Rashid ^a, Ray J Butcher ^b, Sema Öztürk Yildirim ^b,^c, Rizwan Hussain ^d

PMCID: PMC3435797 PMID: 22969643

Abstract

The title compound, C₁₉H₂₆N₂O₃, crystallizes with two independent molecules in the asymmetric unit which differ in the twist of the phenyl rings with respect to the plane of the amide group [the C—C—C—O torsion angles are 121.5 (3) and −119.6 (3)° in the two molecules. Both cyclohexane rings adopt chair conformations. In the crystal, weak C—H⋯O interactions occur. The crystal studied was a non-merohedral twin with a minor component of 4.8 (1)%.

Related literature

For background to N-substituted benzamides, see Priya et al. (2005 ▶). For conformational analysis, see: Cremer & Pople, (1975 ▶). For related structures, see: Toda et al. (1987 ▶); Saeed et al. (2011 ▶).

Experimental

Crystal data

C₁₉H₂₆N₂O₃
M _r = 330.42
Triclinic,
a = 6.1874 (3) Å
b = 10.7109 (4) Å
c = 26.8188 (11) Å
α = 79.128 (4)°
β = 89.027 (4)°
γ = 82.883 (3)°
V = 1731.97 (13) Å³
Z = 4
Cu Kα radiation
μ = 0.69 mm⁻¹
T = 123 K
0.29 × 0.26 × 0.07 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical (Clark & Reid, 1995 ▶) T _min = 0.823, T _max = 0.950
12453 measured reflections
6952 independent reflections
6374 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.080
wR(F ²) = 0.239
S = 1.11
6952 reflections
434 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.29 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035660/ng5286sup1.cif

e-68-o2762-sup1.cif^{(45.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035660/ng5286Isup2.hkl

e-68-o2762-Isup2.hkl^{(340.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812035660/ng5286Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5B—H5BA⋯O3B ⁱ	0.95	2.54	3.148 (4)	122

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Symmetry code: (i) Inline graphic .

Acknowledgments

RJB acknowledges the NSF–MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.

supplementary crystallographic information

Comment

In (I), C₁₉H₂₆N₂O₃, there are two independent molecules (A and B) in the asymmetric unit of the title compound. In molecule A and B the nitro group is almost coplanar with the attached benzene ring in both molecules [C1—C6—N1—O1 = 1.2 (4) ° and C1—C2—N1—O2 = 3.9 (4) ° in molecule A, -3.5 (4) ° and -0.7 (4) ° in molecule B, respectively]. In each molecule, the cyclohexyl rings both adopt a chair conformation as indicated by the puckering parameters Q(2) and φ(2) (Cremer & Pople, 1975) which are 0.012 (1) Å and 177.369 (1) ° in C8A—C13A, 0.015 (1) Å and 122.495 (1) ° in C14A—C19A; 0.017 (1) Å, 21.210 (1) ° in C8B—C13B and 0.013 (1) Å, 230.094 (1) ° in C14A—C19A, respectively. In both molecules, the nitrobenzamide moiety (O3, N2, C7, C8 and C14) is planar (maximum deviation for N2, 0.049 (2) and 0.047 (2) Å in molecules A and B respectively). The dihedral angles between these planar nitrobenzamide moieties and the nitrophenyl groups in molecules A and B are 58.61 (11) and 59.95 (12)° respectively. The main difference in the two molecules lies in how the nitrophenyl rings are arranged with respect to the rest of the molecule and is shown in Figures 1 & 2. This is best illustrated by considering the C3 C4 C7 O3 torsion angle which is 121.46 (33)° in molecule A and -119.62 (34)° in molecule B, thus the phenyl groups in each molecule are twisted in different directions with respect to the plane of the amide moiety. Apart from this the bond lengths and angles in the two molecules agree within experimental error. While there are no classic hydrogen bonds found in the crystal, there are weak C—H···O intra- and intermolecular interactions.

Experimental

To a 250 ml round flask fitted with a condenser was added dicyclohexyl amine (0.1 mol), dichloromethane (15 ml) and triethylamine (0.5 ml. 4-Nitrobenzoyl chloride (0.1 mol) was added. The reaction mixture was stirred at room temperature for 1 h and then refluxed for 2 h. The product precipitated as a colorless powder, which was washed three times with water and dichloromethane. Recrystallization from ethyl acetate produced the crystals of the title compound.