N,N-Dicyclo­hexyl­cyclo­hexa­ne­carboxamide

Sohail Saeed; Naghmana Rashid; Rizwan Hussain; Jerry P Jasinski; Amanda C Keeley

doi:10.1107/S1600536812027766

. 2012 Jun 27;68(Pt 7):o2215. doi: 10.1107/S1600536812027766

N,N-Dicyclohexylcyclohexanecarboxamide

Sohail Saeed ^a,^*, Naghmana Rashid ^a, Rizwan Hussain ^b, Jerry P Jasinski ^c, Amanda C Keeley ^c

PMCID: PMC3394010 PMID: 22798875

Abstract

In the title compound, C₁₉H₃₃NO, all three cyclohexane rings adopt chair conformations. The crystal packing features weak C—H⋯O interactions, forming a supramolecular chain along the c axis.

Related literature

For related studies of N-substituted benzamides, see: Saeed et al. (2011a ▶,b ▶). For a related structure, see: Saeed et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₉H₃₃NO
M _r = 291.46
Monoclinic,
a = 9.8237 (3) Å
b = 16.8736 (5) Å
c = 10.8886 (3) Å
β = 102.890 (3)°
V = 1759.42 (10) Å³
Z = 4
Cu Kα radiation
μ = 0.50 mm⁻¹
T = 173 K
0.44 × 0.38 × 0.18 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.940, T _max = 1.000
10594 measured reflections
3369 independent reflections
3023 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.123
S = 1.05
3369 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); 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/S1600536812027766/tk5114sup1.cif

e-68-o2215-sup1.cif^{(27.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027766/tk5114Isup2.hkl

e-68-o2215-Isup2.hkl^{(165.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812027766/tk5114Isup3.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
C2—H2⋯O1ⁱ	0.98	2.44	3.3861 (13)	163

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Symmetry code: (i) Inline graphic .

Acknowledgments

JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

In connection with on-going studies into N-substituted benzamides (Saeed et al., 2011a; Saeed et al., 2011b), we recently determined the crystal structure of N-(4-bromophenyl)-3,5-dinitrobenzamide (Saeed et al., 2012). In this paper we present the crystal structure of the title compound, (I).

In (I), Fig. 1, all three cyclohexane groups adopt a chair conformation with puckering parameters Q, θ and φ of 0.5850 (14) Å, 0.00 (14)°, and 320 (10)° (C2–C7); 0.517 (13) Å, 178.40 (13)° and 237 (4)° (C8–C13); 0.5747 (15) Å, 0.54 (15)°, and 120 (14)° (C14–C19), respectively (Cremer & Pople, 1975). Crystal packing is stabilized by weak C—H···O intermolecular interactions (Table 1) forming a 1-D supramolecular chain along the c axis (Fig. 2).

Experimental

To a 250 ml round bottom flask fitted with a condenser was added dicyclohexyl amine (0.01 mol), dichloromethane (15 ml) and triethylamine (0.5 ml) with magnetic stirring. Cyclohexanoyl chloride (0.01 mol) was added gradually. The reaction mixture was stirred at room temperature for 1 h and then refluxed for 2 h. The product precipitated as white powder, which was washed three times with water. Recrystallization from ethyl acetate produced the crystals of the title compound.